# Patent

## Title
Pest control composition including novel iminopyridine derivative

## Abstract

Provided is a pest control composition containing an iminopyridine derivative represented by the following Formula (I) and at least one of other pest control agents:




    
    
        [in the formula (I), Ar represents a 5- to 6-membered heterocycle which may be substituted, A represents a heterocycle having a 5- to 10-membered unsaturated bond including one or more nitrogen atoms, and has an imino group substituted with an R group at a position adjacent to the nitrogen atom present on the cycle, Y represents hydrogen, halogen and the like, and R represents any one of groups represented by the following Formulae (a) to (e), (y) or (z)].

## Background
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a pest control composition containing a novel iminopyridine derivative and at least one of other pest control agents.
2. Related Background Art
Although numerous pest control agents have been discovered so far, the development of novel drugs which has high safety is still required in view of the problem of reduction in drug sensitivity, the issue of long-term efficacy, safety to workers or safety in terms of environmental impacts. Further, in agriculture, in order to achieve a reduction in labor for the pest control work, it is general to mix a plurality of components of a chemical for pest control and treat seeds or farm products during the growing seedling period with the chemical, and under these circumstances, it is required to use a long-term residual efficacy type chemical having penetrating and migrating property. In addition, it is also possible to solve problems such as scattering of a chemical to the surrounding environment outside agricultural land or exposure to a person who performs pest control by seed treatment or treatment during the growing seedling period.
European Patent Application Laid-Open No. 432600 (PTL1) discloses a plurality of compounds having the same ring structure as that of a compound represented by Formula (I), but the compounds are used as herbicides and there is no description about pest control.
Japanese Patent Application Laid-Open (JP-A) No. 5-78323 (PTL2) discloses the structural formula of N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound No. 3 in Table 1 of JP-A No. 5-78323), but fails to disclose a preparation method thereof and the compound is not included in a list of the group of compounds that are recognized to have pest control activity (Tables 2 and 3 of JP-A No. 5-78323).
European Patent Application Laid-Open No. 268915 (PTL3) discloses the structural formula of N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Example No. 12 in Table 7 of European Patent Application Laid-Open No. 268915), but fails to disclose a preparation method thereof and the Example does not include the compound as an example of the compounds having pest control activity.
Chemische Berichte (1955), 88, 1103-8 (NPL1) discloses a plurality of compounds having a ring structure similar to that of a compound represented by Formula (I) to be described below, but the compounds are disclosed only as synthetic intermediates.
European Patent Application Laid-Open No. 259738 (PTL4) discloses a plurality of compounds having a ring structure similar to that of a compound represented by Formula (I), but fails to disclose or suggest a compound having a trifluoroacetic acid imino structure.
Furthermore, these documents do not describe pest control activity when the novel iminopyridine derivative of the present invention is mixed with another pest control agent.
SUMMARY OF THE INVENTION
The present invention is contrived to provide a novel pest control agent to solve problems which chemicals in the related art have, such as reduction in drug sensitivity, long-term efficacy, safety during the use thereof and the like in the field of pest control.
In order to solve the problems, the present inventors have intensively studied, and as a result, have found that a novel iminopyridine derivative represented by Formula (I) has excellent pest control effects against pests and discovered a composition showing excellent pest control effects by containing these novel iminopyridine derivatives and at least one of other pest control agents, compared to when a single agent is used, and a use method thereof. The present invention is based on the finding.
Therefore, an object of the present invention is to provide a pest control composition prepared by containing at least one of a novel iminopyridine derivative represented by the following Formula (I) or acid addition salts thereof and at least one of other pest control agents, which is used in a low dose and shows excellent pest control effects against a wide range of pests.
(1) There is provided a pest control composition containing at least one of a novel iminopyridine derivative represented by the following Formula (I) or acid addition salts thereof as an active ingredient and at least one of other pest control agents:




[in the formula (I), Ar represents a phenyl group which may be substituted, a 5- to 6-membered heterocycle which may be substituted, or a 4- to 10-membered heterocycloalkyl group,
A represents a heterocycle having a 5- to 10-membered unsaturated bond including one or more nitrogen atoms, and has an imino group substituted with an R group at a position adjacent to the nitrogen atom present on the cycle,
Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and
R represents any one of groups represented by the following Formulae (a) to (e), (y) or (z),




[here, R1 represents a hydrogen atom, a substituted C1 to C6 alkyl group, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, or a pentafluorophenyl group,
R2 represents a C1 to C6 alkyl group substituted with a halogen atom, an unsubstituted C3 to C6 branched or cyclic alkyl group, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted 5- to 10-membered heterocycle, or a substituted or unsubstituted benzyl group,
R3 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,
R4 represents a hydrogen atom, a formyl group, a C1 to C6 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, a (C1 to C4) alkylthio (C2 to C5) alkynyl group, or a group represented by any of the following Formulae (f) to (n)




here, R4a, R4b and R4c represent a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle group, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,
R4d represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle, and
R4e and R4f each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle,
R5 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,
R6 represents a hydrogen atom, a formyl group, a O,O′-C1 to C4 alkyl phosphoryl group, a C1 to C18 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, a (C1 to C4) alkylthio (C2 to C5) alkynyl group, or a group represented by any of the following Formulae (o) to (x)




here, R6a, R6b and R6c represent a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle group, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, and a (C1 to C4) alkylthio (C2 to C5) alkynyl group,
R6d represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle,
R6e and R6f each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, or a substituted or unsubstituted 5- to 10-membered heterocycle,
R6g and R6h each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle, and
R6i, R6j and R6k each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, or a substituted or unsubstituted (C6 to C10) aryl group), and
R7 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,
Y1 and Y2 represent an oxygen atom or a sulfur atom, and may be the same or different, and
Ry represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, or a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group,
Rz represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group, and n represents 1 or 2],
(2) There is provided the pest control composition according to (1), containing at least one of an amine derivative represented by the following Formula (Ia) or acid addition salts thereof as an active ingredient and at least one of other pest control agents:




[here, Ar represents a pyridyl group which may be substituted with a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, or a pyrimidyl group which may be substituted with a halogen atom, a C1 to C4 alkyl group which may be substituted with a halogen atom, an alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, or a nitro group,
Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and
R1 represents a C1 to C6 alkyl group which is substituted with a halogen atom].
(3) There is provided the pest control composition according to (1), wherein Ar is a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, or a 2-chloro-5-pyrimidyl group.
(4) There is provided the pest control composition according to (1) or (3), wherein in Formula (I), A is the following Formula (A-1):




and Y is a hydrogen atom, a halogen atom, or a cyano group.
(5) There is provided the pest control composition according to (1), (3) to (4), wherein R in Formula (I) is a group with Formula (c).




(6) There is provided the pest control composition according to (1), (3) to (4), wherein R in Formula (I) is a group with Formula (a).




(7) There is provided the pest control composition according to (1), (3) to (4), wherein R in Formula (I) is a group with Formula (d)




and R4 is a C1 to C18 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group, and
R5 is a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, and R5 is a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, or a C2 to C6 alkynyl group which may be substituted with a halogen atom.
(8) There is provided the pest control composition according to (1), wherein the iminopyridine derivative is N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide, or N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide.
(9) There is provided a method for protecting useful plants or animals from pests, including: treating pests, useful plants, seeds of useful plants, soil, cultivation carriers or animals as a target with an effective amount of the pest control composition.
(10) There is provided a combination (combined product) including the iminopyridine derivative represented by Formula (I) and at least one of other pest control agents.
(11) There is provided a use of the pest control composition for protecting useful plants or animals from pests.
It is possible to effectively perform pest control against cabbage moths, Spodoptera litura, aphids, planthoppers, leafhoppers, thrips and other numerous pests by using novel iminopyridine derivative of the present invention.
BRIEF DESCRIPTION OF THE DRAWINGS
A novel iminopyridine derivative represented by Formula (I) may be prepared by the following method.




(I-1) may be obtained by reacting a compound represented by the following Formula (II-1) with a compound represented by ArCH2X [the definition of Ar, A, Y and R1 has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide, and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.
The reaction may be performed usually at 0° C. to 200° C., and it is preferred that reagents are added at 20° C. to 40° C. and the reaction is performed at 60° C. to 80° C.
The compound represented by Formula (II-1) may be obtained by reacting a compound represented by R1-C(═O)X, R1-C(═O)OC(═O)R1, R1C(═O)OR′ [X represents a halogen atom or OTs, OMs and the like, R′ represents a C1 to C6 alkyl group, and the definition of R1, A and Y has the same meaning as the definition described above] and the like with a compound represented by the following Formula (III) in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C. The compound represented by Formula (II-1) may be obtained by reacting the compound represented by Formula (III) with a carboxylic acid represented by R1-COOH [the definition of R1 has the same meaning as the definition described above] using a dehydration condensation agent in the presence or absence of a base, or may be obtained by performing the reaction using phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride in the absence of a base.
It is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide and 1-ethyl-3-(3-[dimethylaminopropyl])carbodiimide hydrochloride as the dehydration condensation agent.
When the reaction is performed in the presence of a base, it is possible to use, for example, a carbonate such as potassium carbonate or sodium carbonate, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.
The reaction is preferably performed by using a solvent, and it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C. The compound represented by Formula (I-1) may be obtained by reacting a compound represented by R1-C(═O)X, R1-C(═O)OC(═O)R1, R1C(═O)OR′ [X represents a halogen atom or OTs, OMs and the like, R′ represents a C1 to C6 alkyl group, and the definition of Ar, A, Y and R1 has the same meaning as the definition described above] and the like with a compound represented by the following Formula (IV) in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C. The compound represented by Formula (I-1) may be obtained by reacting the above-described compound represented by Formula (IV) with a carboxylic acid represented by R1-COOH [the definition of R1 has the same meaning as the definition described above] using a dehydration condensation agent in the presence or absence of a base, or may be obtained by performing the reaction using phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride in the absence of a base.
It is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride as the dehydration condensation agent.
When the reaction is performed in the presence of a base, it is possible to use, for example, a carbonate such as potassium carbonate or sodium carbonate, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.
The reaction is preferably performed by using a solvent, and it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C. The compound represented by Formula (IV) may be obtained by reacting the above-described compound represented by Formula (III) with a compound represented by ArCH2X [the definition of Ar and X has the same meaning as the definition described above] in the presence or absence of a base.
When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but N,N-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.
When Formula (I-1) is synthesized via Formula (II-1) from the compound represented by Formula (III), or when Formula (I-1) is synthesized via Formula (IV) from the compound represented by Formula (III), the reaction may be continuously performed without taking out Formula (II-1) or Formula (IV), or the reactions from Formula (III) to Formula (I-1) may be simultaneously performed in the same vessel.




The compound represented by Formula (I-2) may be obtained by reacting a compound represented by the following Formula (I-2a) with a compound represented by ArCH2X [the definition of Ar, A, Y and R2 has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.
The reaction may be performed usually at 0° C. to 200° C., and it is preferred that reagents are added at 20° C. to 40° C. and the reaction is performed at 60° C. to 80° C.
The compound represented by Formula (I-2a) may be obtained by reacting the above-described compound represented by Formula (III) with a compound represented by R2OC(═O)X (the definition of R2 and X has the same meaning as the definition described above] or represented by the following Formula (I-2b) in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether, and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but acetonitrile, dichloromethane or the like is preferably used.
The reaction may be performed usually at 0° C. to 200° C., and is performed preferably at 20° C. to 80° C.
The compound represented by Formula (I-2) may be obtained by reacting the above-described compound represented by Formula (IV) with a compound represented by R2OC(═O)X (the definition of R2 and X has the same meaning as the definition described above] or represented by the above-described Formula (I-2b) in the presence or absence of a base. When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but acetonitrile, dichloromethane or the like is preferably used.
The reaction may be performed usually at 0° C. to 200° C., and is performed preferably at 20° C. to 80° C.




The compound represented by Formula (I-3) may be synthesized by acting a sulfurizing reagent on a compound (the definition of Ar, A, Y and R3 has the same meaning as the definition described above) represented by the following Formula (II-3a), which may be synthesized in the same manner as described in Formula (I-1), in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base, but potassium carbonate, sodium carbonate or the like is preferably used.
As the sulfurizing reagent, phosphorus pentasulfide, Lawesson's reagent, hydrogen sulfide and the like may be used.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but toluene, tetrahydrofuran or the like is preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C. The compound represented by Formula (I-3) may be obtained by reacting a compound represented by the following Formula (II-3b) with a compound represented by ArCH2X [the definition of Ar, A, Y and R3 has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.
The reaction may be performed usually at 0° C. to 200° C., and it is preferred that reagents are added at 20° C. to 40° C. and the reaction is performed at 60° C. to 80° C.
The compound represented by Formula (II-3b) may be synthesized by acting a sulfurizing reagent on a compound (the definition of A, Y and R3 has the same meaning as the definition described above) represented by Formula (II-3c), which may be synthesized in the same manner as described in Formula (II-1), in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base, but potassium carbonate, sodium carbonate or the like is preferably used.
As the sulfurizing reagent, phosphorus pentasulfide, Lawesson's reagent, hydrogen sulfide and the like may be used. The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but toluene, tetrahydrofuran and the like are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.




The compound represented by Formula (I-4) may be obtained by reacting a compound represented by the following Formula (II-4a), which may be synthesized in the same manner as described in Formula (I-3) with a compound represented by R4-NH2 (the definition of Ar, A, Y, R4 and R5 has the same meaning as the definition described above).




The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but alcohols such as methanol and ethanol are preferably used.
The reaction, if performed in the presence of silver carbonate, copper carbonate and the like, progresses quickly, but may proceed without the compound.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.
The compound represented by Formula (I-4) may be obtained by reacting a compound represented by the following Formula (I-4b) or a salt thereof with R4-X, R4-O—R4 and R4-OR′ (the definition of R4, R′, Ar, A, Y and R5 has the same meaning as the definition described above, and X represents a halogen atom) in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water either alone or in combination of two or more thereof, but toluene, dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C. The compound represented by Formula (I-4b) may be obtained by reacting a compound represented by Formula (II-4a) with ammonia or an alcohol solution thereof, ammonium chloride and the like.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but alcohols such as methanol and ethanol are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C.




The compound represented by Formula (I-5) may be obtained by reacting a compound represented by the following Formula (II-5b) with R6-X (the definition of AR, A, Y, R6 and R7 has the same meaning as the definition described above, and X represents a halogen atom), R6-O—R6 or R6-OR′ (the definition of R′ has the same meaning as the definition described above) in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers, dichloromethane and chloroform are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C.
When R6 represents —C(═O)R6a (R6a has the same meaning as described above), the compound represented by Formula (I-5) may be obtained by reacting the compound represented by Formula (II-5b) with a carboxylic acid represented by R6a-C(═O)OH (the definition of R6a has the same meaning as the definition described above) using a dehydration condensation agent in the presence or absence of a base, or may be obtained by performing the reaction using phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride in the absence of a base.
It is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and the like as the dehydration condensation agent.
When the reaction is performed in the presence of a base, it is possible to use, for example, a carbonate such as potassium carbonate or sodium carbonate, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction is preferably performed by using a solvent, and it is possible to use, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C.
When R6 represents CONR6eR6f (the definition of R6e and R6f has the same meaning as the definition described above, and R6e or R6f represents a hydrogen atom) or CSNR6gR6h (the definition of R6g and R6h has the same meaning as the definition described above, and R6g or R6h represents a hydrogen atom), the compound of Formula (I-5) may be obtained by reacting the Formula (II-5b) with a compound represented by R′′N═C═O (R′′ represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a substituted or unsubstituted (C6 to C10) aryl group, and a substituted or unsubstituted 5- to 10-membered heterocycle) in the presence or absence of a base. When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base. The reaction is preferably performed by using a solvent, and it is possible to use, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but nitriles such as acetonitrile are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.
When R6 represents CONR6eR6f (the definition of R6e and R6f has the same meaning as the definition described above), the compound of Formula (I-5) may be obtained by reacting the above-described compound represented by Formula (II-5b) with a compound represented by the following Formula (II-5c) in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction is preferably performed by using a solvent, and it is possible to use, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but nitriles such as acetonitrile are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.
The compound represented by Formula (II-5b) may be obtained by reacting the compound (the definition of Ar, A, Y and R7 has the same meaning as the definition described above) represented by Formula (II-5a), which may be synthesized in the same manner as described in Formula (I-3) with hydroxylamine or a salt thereof in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.
The compound represented by Formula (I-5) may also be obtained by reacting the compound represented by Formula (II-5a) with a compound represented by R6-ONH2 or a salt thereof in the presence or absence of a base.
When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but alcohols such as methanol and ethanol are preferably used.
The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.
The reaction, if performed in the presence of silver carbonate, copper carbonate and the like, progresses quickly, but may proceed without the compound.




The compound represented by Formula (I-6) [the definition of Ar, A, Y, Y1, Y2, and Ry has the same meaning as the definition described above] may be obtained by reacting according to Phosphorus, sulfur, and silicon and the related elements (2006) 181, 2337-2344.




The compound represented by Formula (I-7) [the definition of Ar, A, Y, Ry and n has the same meaning as the definition described above] may be obtained by reacting a compound represented by the following Formula (II-7a) with a compound represented by ArCH2X [the definition of Ar has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride and the like, a carbonate such as potassium carbonate or sodium carbonate and the like, an alkali metal hydroxide such as potassium hydroxide, sodium hydroxide and the like, tertiary amines such as triethylamine, 1,8-diazabicyclo[4.3.0]non-5-ene and the like, and unsubstituted or substituent-containing pyridines, such as pyridine, 4-dimethylaminopyridine and the like, as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when the solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.
The reaction may be performed usually at from 0° C. to 200° C., and it is preferred that reagents are added at from 20° C. to 40° C. and the reaction is performed at from 60° C. to 80° C.
The compound represented by Formula (II-7a) may be obtained by reacting a compound represented by (II-7b) [X represents a halogen atom, and the definition of Rz and n has the same meaning as the definition described above] with a compound represented by in the following Formula (III) in the presence or absence of a base.




When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride and the like, a carbonate such as potassium carbonate or sodium carbonate and the like, an alkali metal hydroxide such as potassium hydroxide, sodium hydroxide and the like, tertiary amines such as triethylamine, 1,8-diazabicyclo[4.3.0]non-5-ene and the like, and unsubstituted or substituent-containing pyridines, such as pyridine, 4-dimethylaminopyridine and the like, as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when the solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.
The reaction may be performed usually at from 0° C. to 200° C., and it is preferred that reagents are added at from 20° C. to 40° C. and the reaction is performed at from 60° C. to 80° C.
The compound represented by Formula (I-7) may be obtained by reacting a compound represented by (II-7b) [X represents a halogen atom, and the definition of Rz has the same meaning as the definition described above] with a compound represented by in the following Formula (IV) in the presence or absence of a base.
When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride and the like, a carbonate such as potassium carbonate or sodium carbonate and the like, an alkali metal hydroxide such as potassium hydroxide, sodium hydroxide and the like, tertiary amines such as triethylamine, 1,8-diazabicyclo[4.3.0]non-5-ene and the like, and unsubstituted or substituent-containing pyridines, such as pyridine, 4-dimethylaminopyridine and the like, as the base.
The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when the solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.
The reaction may be performed usually at from 0° C. to 200° C., and it is preferred that the reaction is performed at from 0° C. to 80° C.
Examples of a substituent that may be substituted of “a phenyl group which may be substituted” and “a 5- to 6-membered heterocycle which may be substituted”, which are represented by Ar, include a halogen atom, a C1 to C4 alkyl group which may be substituted with a halogen atom, a C1 to C4 alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, a nitro group and the like, preferably a halogen atom, a trifluoromethyl group and a cyano group, and particularly preferably a halogen atom.
Specific examples of the “a phenyl group which may be substituted” represented by Ar of a nitrogen-containing heterocyclic derivative compound having a 2-imino group represented by Formula (I) include a phenyl group and a 3-cyano phenyl group.
“A 5- to 6-membered heterocycle which may be substituted”, represented by Ar of a nitrogen-containing heterocyclic derivative compound having a 2-imino group represented by Formula (I) represents an aromatic 5- to 6-membered heterocycle including one or two of a heteroatom such as an oxygen atom, a sulfur atom or a nitrogen atom, specific examples thereof include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a thiazole ring, an oxazole ring and the like, and preferable aspects thereof include a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-trifluoromethyl-3-pyridyl group, a 6-chloro-3-pyridazinyl group, a 5-chloro-2-pyrazinyl group, a 2-chloro-5-pyrimidinyl group, a 2-chloro-5-thiazolyl group, a 2-chloro-4-pyridyl group, and more preferably a 6-chloro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidinyl group.
Specific examples of “a 4- to 10-membered heterocycloalkyl group” represented by Ar of a nitrogen-containing hetero ring derivative having a 2-imino group represented by Formula (I) include a 2-tetrahydrofuranyl group, a 3-tetrahydrofuranyl group and the like and preferably a 3-tetrahydrofuranyl group. “A heterocycle having a 5- to 10-membered unsaturated bond including one or more nitrogen atoms”, which A of a nitrogen-containing heterocyclic derivative having a 2-imino group represented by Formula (I) represents, means that




in Formula (I) represents any one ring represented by each of the following Formulae A-1 to A-40. In each formula, the end of a double bond is the substitution position of a nitrogen atom.
















The ring is preferably the ring of Formulae A-1, A-13, A-14, A-15, A-16, A-23, A-25, A-38 and A-39 and more preferably the ring of Formula A-1.
“A C1 to C6 alkyl group which may be substituted with a halogen atom”, which Y represents, is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of halogen atoms which may be substituted is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more.
Specific examples of “a C1 to C6 alkyloxy group which may be substituted with a halogen atom” which Y represents include a methoxy group, an ethoxy group, a trifluoromethyloxy group and a difluoromethyloxy group.
A preferred aspect of Y is preferably a hydrogen atom or a halogen atom and more preferably a hydrogen atom.
A preferred aspect of R is a group represented by the Formula (a), (c) and (d) described above.
in Formula (I), “a substituted C1 to C6 alkyl group” which R1 represents is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted substituents is the number of hydrogen atoms which the alkyl group has. Examples of the substituted substituent include a halogen atom, a hydroxyl group, a cyano group, a nitro group, a phenyl group (this phenyl group may be substituted with a C1 to C4 alkyl group which may be substituted with a halogen, a C1 to C4 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), a phenoxy group (this phenyl group may be substituted with a C1 to C4 alkyl group which may be substituted with a halogen, a C1 to C4 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), a benzyloxy group (the phenyl group in this benzyloxy group may be substituted with a C1 to C4 alkyl group which may be substituted with a halogen, a C1 to C4 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), and the like. Specific examples thereof include a 1,1,1-trifluoroethyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 2-cyanoethyl group, a 2-nitroethyl group and the like. A 1,1,1-trifluoroethyl group, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group are preferred, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group are more preferred, and a trifluoromethyl group are particularly preferred.
In Formula (I), “a C1 to C6 alkyl group which may be substituted with a halogen atom” which R3, R5, R7, Ry, and Rz represent is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a trifluoroisopropyl group, and a hexafluoroisopropyl group, and the like.
R3 is each preferably an ethyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group. R5 is preferably a trifluoromethyl group, a trichloromethyl group, a dichloromethyl group, a difluoromethyl group, a difluorochloromethyl group, a chloromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluoromethyl group, a difluorochloromethyl group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group. R7 is preferably a trifluoromethyl group, a trichloromethyl group, a dichloromethyl group, a difluoromethyl group, a difluorochloromethyl group, a chloromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluoromethyl group, a difluorochloromethyl group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group.
Ry is preferably a methyl group, ethyl group, propyl group or isopropyl group. Rz is preferably a methyl group or trifluoromethyl group.
“A C1 to C6 alkyl group which may be substituted with a halogen atom”, which R2 represents, is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 1-(trifluoromethyl)ethyl group, a 1-trifluoromethyl-2,2,2-trifluoroethyl group, a pentafluoroethyl group, and a difluorocyclopropyl group, and the like, and preferred examples thereof include a 2,2,2-trifluoroethyl group, a 1-(trifluoromethyl)ethyl group and a 1-trifluoromethyl-2,2,2-trifluoroethyl group.
“A C1 to C6 alkyl group which may be substituted” which R4 and R6 represent is an alkyl group having 1 to 18 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituents which may be substituted is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more. Examples of the substituent which may be substituted include a halogen atom, a hydroxyl group, a cyano group, a nitro group and the like. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, a t-butyl group, a 3-methyl-2-butyl group, a 3-pentyl group, a 4-heptyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an n-octyl group, an n-tridecyl group, an n-hexadecyl group, an n-octadecyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 2-hydroxyethyl group, a 2-hydroxy-n-propyl group, a 3-hydroxy-n-propyl group, a 2,3-dihydroxy-n-propyl group, a cyanomethyl group, a 2-cyanoethyl group, a 2-nitroethyl group and the like.
R4 is each preferably a methyl group, an ethyl group, a 2,2,2-trifluoroethyl group, a 2,2-difluoroethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, a t-butyl group, a cyclopentyl group, a cyclohexyl group and a 2-hydroxyethyl group, and more preferably a methyl group, an ethyl group and a cyclopropyl group. R6 is preferably a methyl group, an ethyl group, an isopropyl group a cyclopropyl group, a t-butyl group and a cyanomethyl group, and more preferably a methyl group, an ethyl group, a cyclopropyl group and a t-butyl group.
“A C1 to C6 alkyl group which may be substituted with a halogen atom”, which R4a, R4b, R4c, R4d, R4e, R4f, R6a, R6b, R6c, R6d, R6e, R6f, R6g, R6h, R6i, R6j and R6k represent, is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a 2-chloroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group and the like. R6a is preferably a methyl group, an ethyl group, an isopropyl group and a cyclopropyl group. R6b is preferably a methyl group.
“A C2 to C6 alkenyl group which may be substituted with a halogen atom”, which R1, R2, R3, R4, R4a, R4b, R4c, R4d, R4e, R4f, R5, R6, R6a, R6b, R6c, R6d, R6e, R6f, R6g, R6h, R6i, R6j, R6k, R7, Ry and Rz represent, is an alkenyl group having 2 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkenyl group has. When a branched or cyclic alkenyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include an ethenyl group, a 1-propenyl group, a 2-propenyl group, a 2-fluoro-1-propenyl group, a 2-methyl-1-propenyl group and the like, and preferred examples thereof include an ethenyl group.
“A C2 to C6 alkynyl group which may be substituted with a halogen atom”, which R1, R2, R3, R4, R4a, R4b, R4c, R4d, R4e, R4f, R5, R6, R6a, R6b, R6c, R6d, R6e, R6f, R6g, R6h, R6i, R6j, R6k, R7, Ry and Rz represent, is an alkynyl group having 2 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkynyl group has. When a branched or cyclic alkynyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group and the like, and preferred examples thereof include a 1-propynyl group, a 2-propynyl group and a 2-butynyl group.
The (C6 to C10) aryl of “a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group and a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7, Ry and Rz represent, specifically represents a phenyl group and a naphthyl group, and the (C1 to C6) alkyl group, the (C2 to C6) alkenyl group and the (C2 to C6) alkynyl group may have a straight chain, branch or ring. Examples of the substituent which may be substituted with an aryl group include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a phenyl group, a benzyl group, a 2-phenylethyl group, a 2-phenylethenyl group, a 2-phenylethynyl group, a 4-methylphenyl group, a 2-cyanophenyl group, a 3-chlorophenyl group, a 4-methoxyphenyl group, a 3-cyanophenyl group, 1,1-diphenylmethyl group, a naphthylethyl group, a naphthylpropyl group and the like, and preferred examples thereof include a benzyl group and a 2-phenylethyl group, a naphthylethyl group, a naphthylpropyl group.
The (C1 to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group of “a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group and a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7, Ry and Rz represent, may have a straight chain, branch or ring. Examples of the substituent which may be substituted with a phenoxy group include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a phenoxy group, a phenoxymethyl group, a 2-phenoxyethyl group, a 2-phenoxyethenyl group, a 2-phenoxyethynyl group, a 4-chlorophenoxy group, a 2-methylphenoxy group and the like, and preferred examples thereof include a 2-phenoxyethyl group.
The 5- to 10-membered heterocycle of “a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group and a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7, Ry and Rz represent, represents a ring including a hetero atom, such as an oxygen atom, a sulfur atom or a nitrogen atom as an atom constituting 1 to 4 rings, and examples thereof include a furanyl group, a thienyl group, a pyridyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a pyrimidinyl group, a morpholinyl group, a thiazolyl group, an imidazolyl group, a triazolyl group, a tetrahydrofuranyl group, a quinolinyl group and the like. Examples of the substituent which may be substituted with a heterocycle include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. The (C1 to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group may have a straight chain, branch or ring. Specific examples thereof include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-pyridylmethyl group, a 3-pyridylmethyl group, a 4-pyridylmethyl group, a 2-(4-pyridyl)ethenyl group, a 2-(4-pyridyl)ethynyl group, a 2-furanylmethyl group, a 2-thienylmethyl group, a 2-tetrahydrofuranylmethyl group and the like, and preferred examples thereof include a 2-pyridylmethyl group, a 3-pyridylmethyl group, a 4-pyridylmethyl group, a 2-furanylmethyl group, a 2-thienylmethyl group and a 2-tetrahydrofuranylmethyl group.
The (C1 to C4) alkoxy of “a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group and a (C1 to C4) alkoxy (C2 to C5) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R6e, R6f, R7 and Rz represent, represents a (C1 to C4) alkyloxy, alkenyloxy and alkynyloxy having a straight chain, branch or ring. Specific examples thereof include a methoxymethyl group, a 2-methoxyethyl group, an ethoxymethyl group, a 2-ethoxyethyl group, a 3-methoxy-2-propenyl group, a 3-methoxy-2-propynyl group and the like. R4 is preferably a 2-methoxyethyl group.
The (C1 to C4) alkylthio of “a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group and a (C1 to C4) alkylthio (C2 to C5) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R6e, R6f, R7 and Rz represent, represents a (C1 to C4) alkylthio, alkenylthio and alkynylthio having a straight chain, branch or ring. Examples thereof include a methylthiomethyl group, a 2-methylthioethyl group, an ethylthiomethyl group, a 2-ethylthioethyl group, a 3-methylthio-2-propenyl group, a 3-methylthio-2-propynyl group and the like. R4 is preferably a 2-methylthioethyl group.
The (C6 to C10) aryl of “a substituted or unsubstituted (C6 to C10) aryl group”, which R2, R4d, R4e, R4f, R6d, R6e, R6f, R6g, R6h, R6i, R6j and R6k represent, specifically represents a phenyl group and a naphthyl group, and the (C1 to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group may have a straight chain, branch or ring. Examples of the substituent which may be substituted with an aryl group include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methoxyphenyl group, a 4-nitrophenyl group, a 4-cyanophenyl group and the like.
The 5- to 10-membered heterocycle of “a substituted or unsubstituted 5- to 10-membered heterocycle”, which R2, R4d, R4e, R4f, R6d, R6e, R6f, R6g and R6h represent, represents a ring including a hetero atom, such as an oxygen atom, a sulfur atom or a nitrogen atom as an atom constituting 1 to 4 rings, and examples thereof include a furanyl group, a thienyl group, a pyridyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a pyrimidinyl group, a morpholinyl group, a thiazolyl group, an imidazolyl group, a triazolyl group, a tetrahydrofuranyl group, a quinolinyl group and the like. Examples of the substituent which may be substituted with a heterocycle include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-furanyl group, a 2-thienyl group, a 2-tetrahydrofuranyl group and the like.
As a preferred aspect of a compound represented by Formula (I),
R represents the following Formula (a),




Ar represents a 6-chloro-3-pyridyl group, a 2-chloro-5-thiazolyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 2-chloro-5-pyrimidinyl group, a 6-trifluoromethyl-3-pyridyl group and a 2-chloro-5-pyrimidinyl group,
A represents a ring represented by A-1, A-13, A-14, A-15, A-16, A-23 and A-38,
Y represents a hydrogen atom and a 3-cyano group, and
R1 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group, a pentafluoroethyl group, a trifluoroethyl group, an ethenyl group and a 2-propynyl group.
As another preferred aspect of a compound represented by Formula (I),
R represents the following Formula (c),




Ar represents a 6-chloro-3-pyridyl group, a 2-chloro-5-thiazolyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 2-chloro-5-pyrimidyl group and a 6-trifluoromethyl-3-pyridyl group,
A represents a ring represented by A-1,
Y represents a hydrogen atom, and
R3 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group.
As still another preferred aspect of a compound represented by Formula (I),
R represents the following Formula (d),




Ar represents a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidyl group,
A represents a ring represented by A-1,
Y represents a hydrogen atom,
R4 represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, a cyclobutyl group, a cyclohexyl group, and cyclopentyl group, and
R5 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group.
As yet another preferred aspect of a compound represented by Formula (I),
R represents the following Formula (e) group




Ar represents a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidyl group,
A represents a ring represented by A-1,
Y represents a hydrogen atom, and
R6 represents a hydrogen atom, a methyl group, an ethyl group, a 2-propenyl group, a methylcarbonyl group, an ethylcarbonyl group, a cyclopropylcarbonyl group, an ethenylcarbonyl group, a 2-propynylcarbonyl group, a benzoyl group, a 3-pyridylcarbonyl group, a methyloxycarbonyl group and a phenyloxycarbonyl group, and
R7 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group.
Specific examples of the compound of Formula (I) include a compound represented by a combination of the following Table A and Table B.







TABLE 1







Table A













Compound







No.
Ar
A
Y
R
















Table
1-
6-Chloro-3-
A-1
H
represents a


1
5~1-
pyridyl


combination of



710



substituents







corresponding to







each row of Nos. (1







and 6) below of







Table B


Table
2-
2-Chloro-5-
A-1
H
represents a


2
1~2-
thiazolyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
3-
6-Fluoro-3-
A-1
H
represents a


3
2~3-
pyridyl


combination of



710



substituents







corresponding to







each row of Nos. (1







and 3) below of







Table B


Table
4-
6-Bromo-3-
A-1
H
represents a


4
2~4-
pyridyl


combination of



710



substituents







corresponding to







each row of Nos. (1







and 3) below of







Table B


Table
5-
6-Chloro-5-
A-1
H
represents a


5
2~5-
fluoro-3-


combination of



710
pyridyl


substituents







corresponding to







each row of Nos. (1







and 3) below of







Table B


Table
6-
2-Chloro-5-
A-1
H
represents a


6
2~6-
pyrimidinyl


combination of



710



substituents







corresponding to







each row of Nos. (1







and 3) below of







Table B


Table
7-
5-
A-1
H
represents a


7
1~7-
Chloropyrazin-


combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
8-
6-
A-1
H
represents a


8
1~8-
Chloropyridazin-


combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
9-
2-Chloro-5-
A-1
H
represents a


9
1~9-
oxazolyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
10-
6-
A-1
H
represents a


10
1~10-
trifluoromethyl-


combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
11-
3-
A-1
H
represents a


11
1~11-
tetrahydrofu-


combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
12-
2-Chloro-4-
A-1
H
represents a


12
1~12-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
13-
3-Cyanophenyl
A-1
H
represents a


13
1~13-



combination of



710



substituents







corresponding to







each row of







Table B


Table
14-
6-Chloro-3-
A-1
3-
represents a


14
1~14-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
15-
2-Chloro-5-
A-1
3-
represents a


15
1~15-
thiazolyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
16-
6-Fluoro-3-
A-1
3-
represents a


16
1~16-
pyridyI

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
17-
6-Bromo-3-
A-1
3-
represents a


17
1~17-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
18-
6-Chloro-5-
A-1
3-
represents a


18
1~18-
fluoro-3-

F
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
19-
2-Chloro-5-
A-1
3-
represents a


19
1~19-
pyrimidinyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
20-
5-
A-1
3-
represents a


20
1~20-
Chloropyrazin-

F
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
21-
6-
A-1
3-
represents a


21
1~21-
Chloropyridazin-

F
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
22-
2-Chloro-5-
A-1
3-
represents a


22
1~22-
oxazolyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
23-
6-
A-1
3-
represents a


23
1~23-
trifluoromethyl-

F
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
24-
3-
A-1
3-
represents a


24
1~24-
tetrahydrofu-

F
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
25-
6-Chloro-3-
A-1
4-
represents a


25
1~25-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
26-
2-Chloro-5-
A-1
4-
represents a


26
1~26-
thiazolyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
27-
6-Fluoro-3-
A-1
4-
represents a


27
1~27-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
28-
6-Bromo-3-
A-1
4-
represents a


28
1~28-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
29-
6-Chloro-5-
A-1
4-
represents a


29
1~29-
fluoro-3-

F
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
30-
2-Chloro-5-
A-1
4-
represents a


30
1~30-
pyrimidinyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
31-
5-
A-1
4-
represents a


31
1~31-
Chloropyrazin-

F
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
32-
6-
A-1
4-
represents a


32
1~32-
Chloropyridazin-

F
combination of



710
3-yl


substituents







corresponding to







each row of







Table B
















TABLE 2







Table A













Compound







No.
Ar
A
Y
R
















Table
33-
2-Chloro-5-
A-1
4-
represents a


33
1~33-
oxazolyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
34-
6-
A-1
4-
represents a


34
1~34-
trifluoromethyl-

F
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
35-
3-
A-1
4-
represents a


35
1~35-
tetrahydrofu-

F
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
36-
6-Chloro-3-
A-1
5-
represents a


36
1~36-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
37-
2-Chloro-5-
A-1
5-
represents a


37
1~37-
thiazolyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
38-
6-Fluoro-3-
A-1
5-
represents a


38
1~38-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
39-
6-Bromo-3-
A-1
5-
represents a


39
1~39-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
40-
6-Chloro-5-
A-1
5-
represents a


40
1~40-
fluoro-3-

F
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
41-
2-Chloro-5-
A-1
5-
represents a


41
1~41-
pyrimidinyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
42-
5-
A-1
5-
represents a


42
1~42-
Chloropyrazin-

F
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
43-
6-
A-1
5-
represents a


43
1~43-
Chloropyridazin-

F
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
44-
2-Chloro-5-
A-1
5-
represents a


44
1~44-
oxazolyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
45-
6-
A-1
5-
represents a


45
1~45-
trifluoromethyl-

F
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
46-
3-
A-1
5-
represents a


46
1~46-
tetrahydrofu-

F
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
47-
6-Chloro-3-
A-1
6-
represents a


47
1~47-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
48-
2-Chloro-5-
A-1
6-
represents a


48
1~48-
thiazolyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
49-
6-Fluoro-3-
A-1
6-
represents a


49
1~49-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
50-
6-Bromo-3-
A-1
6-
represents a


50
1~50-
pyridyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
51-
6-Chloro-5-
A-1
6-
represents a


51
1~51-
fluoro-3-

F
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
52-
2-Chloro-5-
A-1
6-
represents a


52
1~52-
pyrimidinyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
53-
5-
A-1
6-
represents a


53
1~53-
Chloropyrazin-

F
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
54-
6-
A-1
6-
represents a


54
1~54-
Chloropyridazin-

F
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
55-
2-Chloro-5-
A-1
6-
represents a


55
1~55-
oxazolyl

F
combination of



710



substituents







corresponding to







each row of







Table B


Table
56-
6-
A-1
6-
represents a


56
1~56-
trifluoromethyl-

F
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
57-
3-
A-1
6-
represents a


57
1~57-
tetrahydrofu-

F
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
58-
6-Chloro-3-
A-1
3-
represents a


58
1~58-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
59-
2-Chloro-5-
A-1
3-
represents a


59
1~59-
thiazolyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
60-
6-Fluoro-3-
A-1
3-
represents a


60
1~60-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
61-
6-Bromo-3-
A-1
3-
represents a


61
1~61-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
62-
6-Chloro-5-
A-1
3-
represents a


62
1~62-
fluoro-3-

Cl
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
63-
2-Chloro-5-
A-1
3-
represents a


63
1~63-
pyrimidinyl

Cl
combination of



642



substituents







corresponding to







each row of







Table B


Table
64-
5-
A-1
3-
represents a


64
1~64-
Chloropyrazin-

Cl
combination of



710
2-yl


substituents







corresponding to







each row of







Table B
















TABLE 3







Table A













Compound







No.
Ar
A
Y
R
















Table
65-
6-
A-1
3-
represents a


65
1~65-
Chloropyridazin-

Cl
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
66-
2-Chloro-5-
A-1
3-
represents a


66
1~66-
oxazolyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
67-
6-
A-1
3-
represents a


67
1~67-
trifluoromethyl-

Cl
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
68-
3-
A-1
3-
represents a


68
1~68-
tetrahydrofu-

Cl
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
69-
6-Chloro-3-
A-1
4-
represents a


69
1~69-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
70-
2-Chloro-5-
A-1
4-
represents a


70
1~70-
thiazolyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
71-
6-Fluoro-3-
A-1
4-
represents a


71
1~71-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
72-
6-Bromo-3-
A-1
4-
represents a


72
1~72-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
73-
6-Chloro-5-
A-1
4-
represents a


73
1~73-
fluoro-3-

Cl
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
74-
2-Chloro-5-
A-1
4-
represents a


74
1~74-
pyrimidinyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
75-
5-
A-1
4-
represents a


75
1~75-
Chloropyrazin-

Cl
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
76-
6-
A-1
4-
represents a


76
1~76-
Chloropyridazin-

Cl
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
77-
2-Chloro-5-
A-1
4-
represents a


77
1~77-
oxazolyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
78-
6-
A-1
4-
represents a


78
1~78-
trifluoromethyl-

Cl
combination of



710
3-pyridyI


substituents







corresponding to







each row of







Table B


Table
79-
3-
A-1
4-
represents a


79
1~79-
tetrahydrofu-

Cl
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
80-
6-Chloro-3-
A-1
5-
represents a


80
1~80-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
81-
2-Chloro-5-
A-1
5-
represents a


81
1~81-
thiazolyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
82-
6-Fluoro-3-
A-1
5-
represents a


82
1~82-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
83-
6-Bromo-3-
A-1
5-
represents a


83
1~83-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
84-
6-Chloro-5-
A-1
5-
represents a


84
1~84-
fluoro-3-

Cl
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
85-
2-Chloro-5-
A-1
5-
represents a


85
1~85-
pyrimidinyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
86-
5-
A-1
5-
represents a


86
1~86-
Chloropyrazin-

Cl
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
87-
6-
A-1
5-
represents a


87
1~87-
Chloropyridazin-

Cl
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
88-
2-Chloro-5-
A-1
5-
represents a


88
1~88-
oxazolyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
89-
6-
A-1
5-
represents a


89
1~89-
trifluoromethyl-

Cl
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
90-
3-
A-1
5-
represents a


90
1~90-
tetrahydrofu-

Cl
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
91-
6-Chloro-3-
A-1
6-
represents a


91
1~91-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
92-
2-Chloro-
A-1
6-
represents a


92
1~92-
5-thiazolyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
93-
6-Fluoro-3-
A-1
6-Cl
represents a


93
1~93-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
94-
6-Bromo-3-
A-1
6-
represents a


94
1~94-
pyridyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
95-
6-Chloro-5-
A-1
6-
represents a


95
1~95-
fluoro-3-

Cl
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
96-
2-Chloro-5-
A-1
6-
represents a


96
1~96-
pyrimidinyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B
















TABLE 4







Table A













Compound







No.
Ar
A
Y
R
















Table
97-
5-
A-1
6-
represents a


97
1~97-
Chloropyrazin-

Cl
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
98-
6-
A-1
6-
represents a


98
1~98-
Chloropyridazin-

Cl
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
99-
2-Chloro-5-
A-1
6-
represents a


99
1~99-
oxazolyl

Cl
combination of



710



substituents







corresponding to







each row of







Table B


Table
100-
6-
A-1
6-
represents a


100
1~100-
trifluoromethyl-

Cl
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
101-
3-
A-1
6-
represents a


101
1~101-
tetrahydrofu-

Cl
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
102-
6-Chloro-3-
A-1
3-
represents a


102
1~102-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
103-
2-Chloro-5-
A-1
3-
represents a


103
1~103-
thiazolyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
104-
6-Fluoro-3-
A-1
3-
represents a


104
1~104-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
105-
6-Bromo-3-
A-1
3-
represents a


105
1~105-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
106-
6-Chloro-5-
A-1
3-
represents a


106
1~106-
fluoro-3-

CN
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
107-
2-Chloro-5-
A-1
3-
represents a


107
1~107-
pyrimidinyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
108-
5-
A-1
3-
represents a


108
1~108-
Chloropyrazin-

CN
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
109-
6-
A-1
3-
represents a


109
1~109-
Chloropyridazin-

CN
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
110-
2-Chloro-5-
A-1
3-
represents a


110
1~110-
oxazolyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
111-
6-
A-1
3-
represents a


111
1~111-
trifluoromethyl-

CN
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
112-
3-
A-1
3-
represents a


112
1~112-
tetrahydrofu-

CN
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
113-
6-Chloro-3-
A-1
4-
represents a


113
1~113-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
114-
2-Chloro-5-
A-1
4-
represents a


114
1~114-
thiazolyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
115-
6-Fluoro-3-
A-1
4-
represents a


115
1~115-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
116-
6-Bromo-3-
A-1
4-
represents a


116
1~116-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
117-
6-Chloro-5-
A-1
4-
represents a


117
1~117-
Fluoro-3-

CN
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
118-
2-Chloro-5-
A-1
4-
represents a


118
1~118-
pyrimidinyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
119-
5-
A-1
4-
represents a


119
1~119-
Chloropyrazin-

CN
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
120-
6-
A-1
4-
represents a


120
1~120-
Chloropyridazin-

CN
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
121-
2-Chloro-5-
A-1
4-
represents a


121
1~121-
oxazolyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
122-
6-
A-1
4-
represents a


122
1~122-
trifluoromethyl-

CN
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
123-
3-
A-1
4-
represents a


123
1~123-
tetrahydrofu-

CN
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
124-
6-Chloro-3-
A-1
5-
represents a


124
1~124-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
125-
2-Chloro-5-
A-1
5-
represents a


125
1~155-
thiazolyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
126-
6-Fluoro-3-
A-1
5-
represents a


126
1~126-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
127-
6-Bromo-3-
A-1
5-
represents a


127
1~127-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
128-
6-Chloro-5-
A-1
5-
represents a


128
1~128-
fluoro-3-

CN
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B
















TABLE 5







Table A













Compound







No.
Ar
A
Y
R
















Table
129-
2-Chloro-5-
A-1
5-
represents a


129
1~129-
pyrimidinyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
130-
5-Chloro-
A-1
5-
represents a


130
1~130-
pyrazin-2-yl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
131-
6-Chloro-
A-1
5-
represents a


131
1~131-
pyridazin-3-yl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
132-
2-Chloro-5-
A-1
5-
represents a


132
1~132-
oxazolyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
133-
6-tri-
A-1
5-
represents a


133
1~133-
fluoromethyl-

CN
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
134-
3-tetra-
A-1
5-
represents a


134
1~134-
hydrofuranyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
135-
6-Chloro-
A-1
6-
represents a


135
1~135-
3-pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
136-
2-Chloro-5-
A-1
6-
represents a


136
1~136-
thiazolyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
137-
6-Fluoro-3-
A-1
6-
represents a


137
1~137-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
138-
6-Bromo-3-
A-1
6-
represents a


138
1~138-
pyridyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
139-
6-Chloro-5-
A-1
6-
represents a


139
1~139-
fluoro-3-

CN
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
140-
2-Chloro-5-
A-1
6-
represents a


140
1~140-
pyrimidinyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
141-
5-Chloro-
A-1
6-
represents a


141
1~141-
pyrazin-2-yl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
142-
6-Chloro-
A-1
6-
represents a


142
1~142-
pyridazin-3-yl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
143-
2-Chloro-5-
A-1
6-
represents a


143
1~143-
oxazolyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
144-
6-tri-
A-1
6-
represents a


144
1~144-
fluoromethyl-

CN
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
145-
3-tetra-
A-1
6-
represents a


145
1~145-
hydrofuranyl

CN
combination of



710



substituents







corresponding to







each row of







Table B


Table
146-
6-Chloro-3-
A-1
3-
represents a


146
1~146-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
147-
2-Chloro-5-
A-1
3-
represents a


147
1~147-
thiazolyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
148-
6-Fluoro-3-
A-1
3-
represents a


148
1~148-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
149-
6-Bromo-3-
A-1
3-
represents a


149
1~149-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
150-
6-Chloro-5-
A-1
3-
represents a


150
1~150-
Fluoro-3-

OH
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
151-
2-Chloro-5-
A-1
3-
represents a


151
1~151-
pyrimidinyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
152-
5-Chloro-
A-1
3-
represents a


152
1~152-
pyrazin-2-yl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
153-
6-Chloro-
A-1
3-
represents a


153
1~153-
pyridazin-3-yl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
154-
2-Chloro-5-
A-1
3-
represents a


154
1~154-
oxazolyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
155-
6-tri-
A-1
3-
represents a


155
1~155-
fluoromethyl-

OH
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
156-
3-tetra-
A-1
3-
represents a


156
1~156-
hydrofuranyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
157-
6-Chloro-3-
A-1
4-
represents a


157
1~157-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
158-
2-Chloro-5-
A-1
4-
represents a


158
1~158-
thiazolyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
159-
6-Fluoro-3-
A-1
4-
represents a


159
1~159-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
160-
6-Bromo-3-
A-1
4-
represents a


160
1~160-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B
















TABLE 6







Table A













Compound







No.
Ar
A
Y
R
















Table
161-
6-Chloro-5-
A-1
4-
represents a


161
1~161-
fluoro-3-

OH
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
162-
2-Chloro-5-
A-1
4-
represents a


162
1~162-
pyrimidinyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
163-
5-Chloro-
A-1
4-
represents a


163
1~163-
pyrazin-2-yl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
164-
6-Chloro-
A-1
4-
represents a


164
1~164-
pyridazin-3-yl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
165-
2-Chloro-5-
A-1
4-
represents a


165
1~165-
oxazolyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
166-
6-tri-
A-1
4-
represents a


166
1~166-
fluoromethyl-

OH
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
167-
3-tetra-
A-1
4-
represents a


167
1~167-
hydrofuranyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
168-
6-Chloro-3-
A-1
5-
represents a


168
1~168-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
169-
2-Chloro-5-
A-1
5-
represents a


169
1~169-
thiazolyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
170-
6-Fluoro-3-
A-1
5-
represents a


170
1~170-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
171-
6-Bromo-3-
A-1
5-
represents a


171
1~171-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
172-
6-Chloro-5-
A-1
5-
represents a


172
1~172-
fluoro-3-

OH
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
173-
2-Chloro-5-
A-1
5-
represents a


173
1~173-
pyrimidinyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
174-
5-Chloro-
A-1
5-
represents a


174
1~174-
pyrazin-2-yl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
175-
6-Chloro-
A-1
5-
represents a


175
1~175-
pyridazin-3-yl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
176-
2-Chloro-5-
A-1
5-
represents a


176
1~176-
oxazolyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
177-
6-tri-
A-1
5-
represents a


177
1~77-
fluoromethyl-

OH
combination of



710
3-pyridyI


substituents







corresponding to







each row of







Table B


Table
178-
3-tetra-
A-1
5-
represents a


178
1~178-
hydrofuranyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
179-
6-Chloro-3-
A-1
6-
represents a


179
1~179-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
180-
2-Chloro-5-
A-1
6-
represents a


180
1~180-
thiazolyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
181-
6-Fluoro-3-
A-1
6-
represents a


181
1~181-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
182-
6-Bromo-3-
A-1
6-
represents a


182
1~182-
pyridyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
183-
6-Chloro-5-
A-1
6-
represents a


183
1~183-
fluoro-3-

OH
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
184-
2-Chloro-5-
A-1
6-
represents a


184
1~184-
pyrimidinyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
185-
5-Chloro-
A-1
6-
represents a


185
1~185-
pyrazin-2-yl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
186-
6-Chloro-
A-1
6-
represents a


186
1~186-
pyridazin-3-yl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
187-
2-Chloro-5-
A-1
6-
represents a


187
1~187-
oxazolyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
188-
6-tri-
A-1
6-
represents a


188
1~188-
fluoromethyl-

OH
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
189-
3-tetra-
A-1
6-
represents a


189
1~189-
hydrofuranyl

OH
combination of



710



substituents







corresponding to







each row of







Table B


Table
190-
6-Chloro-3-
A-13
H
represents a


190
1~190-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
191-
2-Chloro-5-
A-13
H
represents a


191
1~191-
thiazolyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
192-
6-Fluoro-3-
A-13
H
represents a


192
1~192-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B
















TABLE 7







Table A













Compound







No.
Ar
A
Y
R
















Table
193-
6-Bromo-3-
A-13
H
represents a


193
1~193-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
194-
6-Chloro-5-
A-13
H
represents a


194
1~194-
fluoro-3-


combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
195-
2-Chloro-5-
A-13
H
represents a


195
1~195-
pyrimidinyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
196-
5-Chloro-
A-13
H
represents a


196
1~196-
pyrazin-2-yl


combination of



710



substituents







corresponding to







each row of







Table B


Table
197-
6-Chloro-
A-13
H
represents a


197
1~197-
pyridazin-3-yl


combination of



710



substituents







corresponding to







each row of







Table B


Table
198-
2-Chloro-5-
A-13
H
represents a


198
1~198-
oxazolyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
199-
6-tri-
A-13
H
represents a


199
1~199-
fluoromethyl-


combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
200-
3-tetra-
A-13
H
represents a


200
1~200-
hydrofuranyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
201-
6-Chloro-3-
A-14
H
represents a


201
1~201-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
202-
2-Chloro-5-
A-14
H
represents a


202
1~202-
thiazolyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
203-
6-Fluoro-3-
A-14
H
represents a


203
1~203-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
204-
6-Bromo-3-
A-14
H
represents a


204
1~204-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
205-
6-Chloro-5-
A-14
H
represents a


205
1~205-
fluoro-3-


combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
206-
2-Chloro-5-
A-14
H
represents a


206
1~206-
pyrimidinyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
207-
5-Chloro-
A-14
H
represents a


207
1~207-
pyrazin-2-yl


combination of



710



substituents







corresponding to







each row of







Table B


Table
208-
6-Chloro-
A-14
H
represents a


208
1~208-
pyridazin-3-yl


combination of



710



substituents







corresponding to







each row of







Table B


Table
209-
2-Chloro-5-
A-14
H
represents a


209
1~209-
oxazolyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
210-
6-tri-
A-14
H
represents a


210
1~210-
fluoromethyl-


combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
211-
3-tetra-
A-14
H
represents a


211
1~211-
hydrofuranyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
212-
6-Chloro-3-
A-15
H
represents a


212
1~212-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
213-
2-Chloro-5-
A-15
H
represents a


213
1~213-
thiazolyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
214-
6-Fluoro-3-
A-15
H
represents a


214
1~214-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
215-
6-Bromo-3-
A-15
H
represents a


215
1~215-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
216-
6-Chloro-5-
A-15
H
represents a


216
1~216-
fluoro-3-


combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
217-
2-Chloro-5-
A-15
H
represents a


217
1~217-
pyrimidinyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
218-
5-Chloro-
A-15
H
represents a


218
1~218-
pyrazin-2-yl


combination of



710



substituents







corresponding to







each row of







Table B


Table
219-
6-Chloro-
A-15
H
represents a


219
1~219-
pyridazin-3-yl


combination of



710



substituents







corresponding to







each row of







Table B


Table
220-
2-Chloro-5-
A-15
H
represents a


220
1~220-
oxazolyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
221-
6-tri-
A-15
H
represents a


221
1~221-
fluoromethyl-


combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
222-
3-tetra-
A-15
H
represents a


222
1~222-
hydrofuranyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
223-
6-Chloro-3-
A-16
H
represents a


223
1~223-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
224-
2-Chloro-5-
A-16
H
represents a


224
1~224-
thiazolyl


combination of



710



substituents







corresponding to







each row of







Table B
















TABLE 8







Table A













Compound







No.
Ar
A
Y
R
















Table
225-
6-Fluoro-3-
A-16
H
represents a


225
1~225-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
226-
6-Bromo-3-
A-16
H
represents a


226
1~226-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
227-
6-Chloro-5-
A-16
H
represents a


227
1~227-
fluoro-3-


combination of



710
pyridyl


substituents







corresponding







to each row of







Table B


Table
228-
2-Chloro-5-
A-16
H
represents a


228
1~228-
pyrimidinyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
229-
5-Chloro-
A-16
H
represents a


229
1~229-
pyrazin-2-yl


combination of



710



substituents







corresponding







to each row of







Table B


Table
230-
6-Chloro-
A-16
H
represents a


230
1~230-
pyridazin-3-yl


combination of



710



substituents







corresponding







to each row of







Table B


Table
231-
2-Chloro-5-
A-16
H
represents a


231
1~231-
oxazolyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
232-
6-tri-
A-16
H
represents a


232
1~232-
fluoromethyl-


combination of



710
3-pyridyl


substituents







corresponding







to each row of







Table B


Table
233-
3-tetra-
A-16
H
represents a


233
1~233-
hydrofuranyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
234-
6-Chloro-3-
A-2
H
represents a


234
1~234-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
235-
6-Chloro-3-
A-3
H
represents a


235
1~235-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
236-
6-Chloro-3-
A-4
H
represents a


236
1~236-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
237-
6-Chloro-3-
A-5
H
represents a


237
1~237-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
238-
6-Chloro-3-
A-6
H
represents a


238
1~238-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
239-
6-Chloro-3-
A-7
H
represents a


239
1~239-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
240-
6-Chloro-3-
A-8
H
represents a


240
1~240-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
241-
6-Chloro-3-
A-9
H
represents a


241
1~241-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
242-
6-Chloro~3-
A-10
H
represents a


242
1~242-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
243-
6-Chloro-3-
A-11
H
represents a


243
1~243-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
244-
6-Chloro-3-
A-12
H
represents a


244
1~244-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
245-
6-Chloro-3-
A-17
H
represents a


245
1~245-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
246-
6-Chloro-3-
A-18
H
represents a


246
1~246-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
247-
6-Chloro-3-
A-19
H
represents a


247
1~247-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
248-
6-Chloro-3-
A-20
H
represents a


248
1~248-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
249-
6-Chloro-3-
A-21
H
represents a


249
1~249-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
250-
6-Chloro-3-
A-22
H
represents a


250
1~250-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
251-
6-Chloro-3-
A-23
H
represents a


251
1~251-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
252-
6-Chloro-3-
A-24
H
represents a


252
1~252-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
253-
6-Chloro-3-
A-25
H
represents a


253
1~253-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
254-
6-Chloro-3-
A-26
H
represents a


254
1~254-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
255-
6-Chloro-3-
A-27
H
represents a


255
1~255-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
256-
6-Chloro-3-
A-28
H
represents a


256
1~256-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B
















TABLE 9







Table A













Compound







No.
Ar
A
Y
R
















Table
257-
6-Chloro-3-
A-29
H
represents a


257
1~257-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
258-
6-Chloro-3-
A-30
H
represents a


258
1~258-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
259-
6-Chloro-3-
A-31
H
represents a


259
1~259-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
260-
6-Chloro-3-
A-32
H
represents a


260
1~260-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
261-
6-Chloro-3-
A-33
H
represents a


261
1~261-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
262-
6-Chloro-3-
A-34
H
represents a


262
1~262-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
263-
6-Chloro-3-
A-35
H
represents a


263
1~263-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
264-
6-Chloro-3-
A-36
H
represents a


264
1~264-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
265-
6-Chloro-3-
A-37
H
represents a


265
1~265-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
266-
6-Chloro-3-
A-38
H
represents a


266
1~266-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
267-
6-Chloro-3-
A-39
H
represents a


267
1~267-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
268-
6-Chloro-3-
A-40
H
represents a


268
1~268-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
269-
6-Chloro-3-
A-2
H
represents a


269
1-269-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
270-
6-Chloro-3-
A-3
H
represents a


270
1~270-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
271-
6-Chloro-3-
A-4
H
represents a


271
1~271-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
272-
6-Chloro-3-
A-5
H
represents a


272
1~272-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
273-
6-Chloro-3-
A-6
H
represents a


273
1~273-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
274-
6-Chloro-3-
A-7
H
represents a


274
1~274-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
275-
6-Chloro-3-
A-8
H
represents a


275
1~275-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
276-
6-Chloro-3-
A-9
H
represents a


276
1~276-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
277-
6-Chloro-3-
A-10
H
represents a


277
1~277-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
278-
6-Chloro-3-
A-11
H
represents a


278
1~278-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
279-
6-Chloro-3-
A-12
H
represents a


279
1~279-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
280-
6-Chloro-3-
A-17
H
represents a


280
1~280-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
281-
6-Chloro-3-
A-18
H
represents a


281
1~281-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
282-
6-Chloro-3-
A-19
H
represents a


282
1~282-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
283-
6-Chloro-3-
A-20
H
represents a


283
1~283-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
284-
6-Chloro-3-
A-21
H
represents a


284
1~284-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
285-
6-Chloro-3-
A-22
H
represents a


285
1~285-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
286-
6-Chloro-3-
A-23
H
represents a


286
1~286-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
287-
6-Chloro-3-
A-24
H
represents a


287
1~287-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
288-
6-Chloro-3-
A-25
H
represents a


288
1~288-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B






















TABLE A







Compound







No.
Ar
A
Y
R





















Table
289-
6-Chloro-3-
A-
H
represents a


289
1~289-
pyridyl
26

combination of



710



substituents







corresponding







to each row of







Table B


Table
290-
6-Chloro-3-
A-
H
represents a


290
1~290-
pyridyl
27

combination of



710



substituents







corresponding







to each row of







Table B


Table
291-
6-Chloro-3-
A-
H
represents a


291
1~291-
pyridyl
28

combination of



710



substituents







corresponding







to each row of







Table B


Table
292-
6-Chloro-3-
A-
H
represents a


292
1~292-
pyridyl
29

combination of



710



substituents







corresponding







to each row of







Table B


Table
293-
6-Chloro-3-
A-
H
represents a


293
1~293-
pyridyl
30

combination of



710



substituents







corresponding







to each row of







Table B


Table
294-
6-Chloro-3-
A-
H
represents a


294
1~294-
pyridyl
31

combination of



710



substituents







corresponding







to each row of







Table B


Table
295-
6-Chloro-3-
A-
H
represents a


295
1~295-
pyridyl
32

combination of



710



substituents







corresponding







to each row of







Table B


Table
296-
6-Chloro-3-
A-
H
represents a


296
1~296-
pyridyl
33

combination of



710



substituents







corresponding







to each row of







Table B


Table
297-
6-Chloro-3-
A-
H
represents a


297
1~297-
pyridyl
34

combination of



710



substituents







corresponding







to each row of







Table B


Table
298-
6-Chloro-3-
A-
H
represents a


298
1~298-
pyridyl
35

combination of



710



substituents







corresponding







to each row of







Table B


Table
299-
6-Chloro-3-
A-
H
represents a


299
1~299-
pyridyl
36

combination of



710



substituents







corresponding







to each row of







Table B


Table
300-
6-Chloro-3-
A-
H
represents a


300
1~300-
pyridyl
37

combination of



710



substituents







corresponding







to each row of







Table B


Table
301-
6-Chloro-3-
A-
H
represents a


301
1~301-
pyridyl
38

combination of



710



substituents







corresponding







to each row of







Table B


Table
302-
6-Chloro-3-
A-
H
represents a


302
1~302-
pyridyl
39

combination of



710



substituents







corresponding







to each row of







Table B


Table
303-
6-Chloro-3-
A-
H
represents a


303
1~303-
pyridyl
40

combination of



710



substituents







corresponding







to each row of







Table B


Table
304-
6-Chloro-3-
A-2
H
represents a


304
1~304-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
305-
6-Chloro-3-
A-3
H
represents a


305
1~305-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
306-
6-Chloro-3-
A-4
H
represents a


306
1~306-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
307-
6-Chloro-3-
A-5
H
represents a


307
1~307-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
308-
6-Chloro-3-
A-6
H
represents a


308
1~308-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
309-
6-Chloro-3-
A-7
H
represents a


309
1~309-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
310-
6-Chloro-3-
A-8
H
represents a


310
1~310-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
311-
6-Chloro-3-
A-9
H
represents a


311
1~311-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
312-
6-Chloro-3-
A-
H
represents a


312
1~312-
pyridyl
10

combination of



710



substituents







corresponding







to each row of







Table B


Table
313-
6-Chloro-3-
A-
H
represents a


313
1~313-
pyridyl
11

combination of



710



substituents







corresponding







to each row of







Table B


Table
314-
6-Chloro-3-
A-
H
represents a


314
1~314-
pyridyl
12

combination of



710



substituents







corresponding







to each row of







Table B


Table
315-
6-Chloro-3-
A-
H
represents a


315
1~315-
pyridyl
17

combination of



710



substituents







corresponding







to each row of







Table B


Table
316-
6-Chloro-3-
A-
H
represents a


316
1~316-
pyridyl
18

combination of



710



substituents







corresponding







to each row of







Table B


Table
317-
6-Chloro-3-
A-
H
represents a


317
1~317-
pyridyl
19

combination of



710



substituents







corresponding







to each row of







Table B


Table
318-
6-Chloro-3-
A-
H
represents a


318
1~318-
pyridyl
20

combination of



710



substituents







corresponding







to each row of







Table B


Table
319-
6-Chloro-3-
A-
H
represents a


319
1~319-
pyridyl
21

combination of



710



substituents







corresponding







to each row of







Table B


Table
320-
6-Chloro-3-
A-
H
represents a


320
1~320-
pyridyl
22

combination of



710



substituents







corresponding







to each row of







Table B






















TABLE A







Com-







pound



No
Ar
A
Y
R





















Table
321-
6-Chloro-3-
A-
H
represents a


321
1~321-
pyridyl
23

combination of



710



substituents







corresponding to







each row of Table B


Table
322-
6-Chloro-3-
A-
H
represents a


322
1~322-
pyridyl
24

combination of



710



substituents







corresponding to







each row of Table B


Table
323-
6-Chloro-3-
A-
H
represents a


323
1~323-
pyridyl
25

combination of



710



substituents







corresponding to







each row of Table B


Table
324-
6-Chloro-3-
A-
H
represents a


324
1~324-
pyridyl
26

combination of



710



substituents







corresponding to







each row of Table B


Table
325-
6-Chloro-3-
A-
H
represents a


325
1~325-
pyridyl
27

combination of



710



substituents







corresponding to







each row of







Table B


Table
326-
6-Chloro-3-
A-
H
represents a


326
1~326-
pyridyl
28

combination of



710



substituents







corresponding to







each row of







Table B


Table
327-
6-Chloro-3-
A-
H
represents a


327
1~327-
pyridyl
29

combination of



710



substituents







corresponding to







each row of







Table B


Table
328-
6-Chloro-3-
A-
H
represents a


328
1~328-
pyridyl
30

combination of



710



substituents







corresponding to







each row of







Table B


Table
329-
6-Chloro-3-
A-
H
represents a


329
1~329-
pyridyl
31

combination of



710



substituents







corresponding to







each row of







Table B


Table
330-
6-Chloro-3-
A-
H
represents a


330
1~330-
pyridyl
32

combination of



710



substituents







corresponding to







each row of







Table B


Table
331-
6-Chloro-3-
A-
H
represents a


331
1~331-
pyridyl
33

combination of



710



substituents







corresponding to







each row of







Table B


Table
332-
6-Chloro-3-
A-
H
represents a


332
1~332-
pyridyl
34

combination of



710



substituents







corresponding to







each row of







Table B


Table
333-
6-Chloro-3-
A-
H
represents a


333
1~333-
pyridyl
35

combination of



710



substituents







corresponding to







each row of







Table B


Table
334-
6-Chloro-3-
A-
H
represents a


334
1~334-
pyridyl
36

combination of



710



substituents







corresponding to







each row of







Table B


Table
335-
6-Chloro-3-
A-
H
represents a


335
1~335-
pyridyl
37

combination of



710



substituents







corresponding to







each row of







Table B


Table
336-
6-Chloro-3-
A-
H
represents a


336
1~336-
pyridyl
38

combination of



710



substituents







corresponding to







each row of







Table B


Table
337-
6-Chloro-3-
A-
H
represents a


337
1~337-
pyridyl
39

combination of



710



substituents







corresponding to







each row of







Table B


Table
338-
6-Chloro-3-
A-
H
represents a


338
1~338-
pyridyl
40

combination of



710



substituents







corresponding to







each row of







Table B


Table
339-
2-Chloro-5-
A-2
H
represents a


339
1~339-
thiazolyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
340-
3-
A-3
H
represents a


340
1~340-
Trifluoromethylphenyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
341-
2-
A-4
H
represents a


341
1~341-
Methylphenyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
342-
3-
A-5
H
represents a


342
1~342-
Methylphenyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
343-
4-
A-6
H
represents a


343
1~343-
Methylphenyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
344-
4-
A-7
H
represents a


344
1~344-
Trifluoromethylphenyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
345-
2-
A-8
H
represents a


345
1~345-
Trifluoromethylphenyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
346-
2-
A-9
H
represents a


346
1~346-
Methoxyphenyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
347-
3-
A-
H
represents a


347
1~347-
Methoxyphenyl
10

combination of



710



substituents







corresponding to







each row of







Table B


Table
348-
4-
A-
H
represents a


348
1~348-
Methoxyphenyl
11

combination of



710



substituents







corresponding to







each row of







Table B


Table
349-
2-Cyanophenyl
A-
H
represents a


349
1~349-

12

combination of



710



substituents







corresponding to







each row of







Table B


Table
350-
3-Cyanophenyl
A-
H
represents a


350
1~350-

17

combination of



710



substituents







corresponding to







each row of







Table B


Table
351-
4-Cyanophenyl
A-
H
represents a


351
1~351-

18

combination of



710



substituents







corresponding to







each row of







Table B


Table
352-
2-Nitrophenyl
A-
H
represents a


352
1~352-

19

combination of



710



substituents







corresponding to







each row of







Table B






















TABLE A







Compound







No
Ar
A
Y
R





















Table
353-
3-Nitrophenyl
A-
H
represents a


353
1~353-

20

combination of



710



substituents







corresponding to







each row of Table B


Table
354-
4-Nitrophenyl
A-
H
represents a


354
1~354-

21

combination of



710



substituents







corresponding to







each row of Table B


Table
355-
3-Hydroxy-2-
A-
H
represents a


355
1~355-
pyridyl
22

combination of



710



substituents







corresponding to







each row of Table B


Table
356-
4-hydroxy-2-
A-
H
represents a


356
1~356-
pyridyl
23

combination of



710



substituents







corresponding to







each row of Table B


Table
357-
5-hydroxy-2-
A-
H
represents a


357
1~357-
pyridyl
24

combination of



710



substituents







corresponding to







each row of







Table B


Table
358-
6-hydroxy-2-
A-
H
represents a


358
1~358-
pyridyl
25

combination of



710



substituents







corresponding to







each row of







Table B


Table
359-
2-Hydroxy-3-
A-
H
represents a


359
1~359-
pyridyl
26

combination of



710



substituents







corresponding to







each row of







Table B


Table
360-
5-Hydroxy-3-
A-
H
represents a


360
1~360-
pyridyl
27

combination of



710



substituents







corresponding to







each row of







Table B


Table
361-
6-Hydroxy-3-
A-
H
represents a


361
1~361-
pyridyl
28

combination of



710



substituents







corresponding to







each row of







Table B


Table
362-
4-Hydroxy-3-
A-
H
represents a


362
1~362-
pyridyl
29

combination of



710



substituents







corresponding to







each row of







Table B


Table
363-
2-Hydroxy-4-
A-
H
represents a


363
1~363-
pyridyl
30

combination of



710



substituents







corresponding to







each row of







Table B


Table
364-
3-Hydroxy-4-
A-
H
represents a


364
1~364-
pyridyl
31

combination of



710



substituents







corresponding to







each row of







Table B


Table
365-
3-Chloro-2-
A-
H
represents a


365
1~365-
pyridyl
32

combination of



710



substituents







corresponding to







each row of







Table B


Table
366-
4-Chloro-2-
A-
H
represents a


366
1~366-
pyridyl
33

combination of



710



substituents







corresponding to







each row of







Table B


Table
367-
5-Chloro-2-
A-
H
represents a


367
1~367-
pyridyl
34

combination of



710



substituents







corresponding to







each row of







Table B


Table
368-
6-Chloro-2-
A-
H
represents a


368
1~368-
pyridyl
35

combination of



710



substituents







corresponding to







each row of







Table B


Table
369-
2-Chloro-3-
A-
H
represents a


369
1~369-
pyridyl
36

combination of



710



substituents







corresponding to







each row of







Table B


Table
370-
5-Chloro-3-
A-
H
represents a


370
1~370-
pyridyl
37

combination of



710



substituents







corresponding to







each row of







Table B


Table
371-
6-Chloro-3-
A-
H
represents a


371
1~371-
pyridyl
38

combination of



710



substituents







corresponding to







each row of







Table B


Table
372-
4-Chloro-3-
A-
H
represents a


372
1~372-
pyridyl
39

combination of



710



substituents







corresponding to







each row of







Table B


Table
373-
2-Chloro-4-
A-
H
represents a


373
1~373-
pyridyl
40

combination of



710



substituents







corresponding to







each row of







Table B


Table
374-
3-Chloro-4-
A-2
H
represents a


374
1~374-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
375-
3-bromo-2-
A-3
H
represents a


375
1~375-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
376-
4-bromo-2-
A-4
H
represents a


376
1~376-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
377-
5-bromo-2-
A-5
H
represents a


377
1~377-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
378-
6-bromo-2-
A-6
H
represents a


378
1~378-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
379-
2-bromo-3-
A-7
H
represents a


379
1~379-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
380-
5-bromo-3-
A-8
H
represents a


380
1~380-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
381-
6-bromo-3-
A-9
H
represents a


381
1~381-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
382-
4-bromo-3-
A-
H
represents a


382
1~382-
pyridyl
10

combination of



710



substituents







corresponding to







each row of







Table B


Table
383-
2-bromo-4-
A-
H
represents a


383
1~383-
pyridyl
11

combination of



710



substituents







corresponding to







each row of







Table B


Table
384-
3-bromo-4-
A-
H
represents a


384
1~384-
pyridyl
12

combination of



710



substituents







corresponding to







each row of







Table B






















TABLE A







Compound







No
Ar
A
Y
R





















Table
385-
3-Fluoro-2-
A-
H
represents a


385
1~385-
pyridyl
17

combination of



710



substituents







corresponding







to each row of







Table B


Table
386-
4-Fluoro-2-
A-
H
represents a


386
1~386-
pyridyl
18

combination of



710



substituents







corresponding







to each row of







Table B


Table
387-
5-Fluoro-2-
A-
H
represents a


387
1~387-
pyridyl
19

combination of



710



substituents







corresponding







to each row of







Table B


Table
388-
6-Fluoro-2-
A-
H
represents a


388
1~388-
pyridyl
20

combination of



710



substituents







corresponding







to each row of







Table B


Table
389-
2-Fluoro-3-
A-
H
represents a


389
1~389-
pyridyl
21

combination of



710



substituents







corresponding







to each row of







Table B


Table
390-
5-Fluoro-3-
A-
H
represents a


390
1~390-
pyridyl
22

combination of



710



substituents







corresponding







to each row of







Table B


Table
391-
6-Fluoro-3-
A-
H
represents a


391
1~391-
pyridyl
23

combination of



710



substituents







corresponding







to each row of







Table B


Table
392-
4-Fluoro-3-
A-
H
represents a


392
1~392-
pyridyl
24

combination of



710



substituents







corresponding







to each row of







Table B


Table
393-
2-Fluoro-4-
A-
H
represents a


393
1~393-
pyridyl
25

combination of



710



substituents







corresponding







to each row of







Table B


Table
394-
3-Fluoro-4-
A-
H
represents a


394
1~394-
pyridyl
26

combination of



710



substituents







corresponding







to each row of







Table B


Table
395-
6-Fluoro-3-
A-
H
represents a


395
1~395-
pyridyl
27

combination of



710



substituents







corresponding







to each row of







Table B


Table
396-
3-iodo-2-
A-
H
represents a


396
1~396-
pyridyl
28

combination of



710



substituents







corresponding







to each row of







Table B


Table
397-
4-iodo-2-
A-
H
represents a


397
1~397-
pyridyl
29

combination of



710



substituents







corresponding







to each row of







Table B


Table
398-
5-iodo-2-
A-
H
represents a


398
1~398-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
399-
6-iodo-
A-
H
represents a


399
1~399-
2~pyridyl
31

combination of



710



substituents







corresponding







to each row of







Table B


Table
400-
2-iodo-3-
A-
H
represents a


400
1~400-
pyridyl
32

combination of



710



substituents







corresponding







to each row of







Table B


Table
401-
5-iodo-3-
A-
H
represents a


401
1~401-
pyridyl
33

combination of



710



substituents







corresponding







to each row of







Table B


Table
402-
6-iodo-3-
A-
H
represents a


402
1~402-
pyridyl
34

combination of



710



substituents







corresponding







to each row of







Table B


Table
403-
4-iodo~3-
A-
H
represents a


403
1~403-
pyridyl
35

combination of



710



substituents







corresponding







to each row of







Table B


Table
404-
2-iodo-4-
A-
H
represents a


404
1~404-
pyridyl
36

combination of



710



substituents







corresponding







to each row of







Table B


Table
405-
3-iodo-4-
A-
H
represents a


405
1~405-
pyridyl
37

combination of



710



substituents







corresponding







to each row of







Table B


Table
406-
6-iodo-3-
A-
H
represents a


406
1~406-
pyridyl
38

combination of



710



substituents







corresponding







to each row of







Table B


Table
407-
6-iodo-3-
A-
H
represents a


407
1~407-
pyridyl
39

combination of



710



substituents







corresponding







to each row of







Table B


Table
408-
2-
A-
H
represents a


408
1~408-
tetrahydrofuranyl
40

combination of



710



substituents







corresponding







to each row of







Table B


Table
409-
3-
A-2
H
represents a


409
1~409-
tetrahydrofuranyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
410-
5-Chloro-2-
A-3
H
represents a


410
1~410-
thiazolyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
411-
6-Fluoro-3-
A-4
H
represents a


411
1~411-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
412-
6-Bromo-3-
A-5
H
represents a


412
1~412-
pyridyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
413-
6-Chloro-5-
A-6
H
represents a


413
1~413-
Fluoro-3-


combination of



710
pyridyl


substituents







corresponding







to each row of







Table B


Table
414-
3,5-
A-7
H
represents a


414
1~414-
Dimethylphenyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
415-
2,3-
A-8
H
represents a


415
1~415-
Dimethylphenyl


combination of



710



substituents







corresponding







to each row of







Table B


Table
416-
2,4-
A-9
H
represents a


416
1~416-
Dimethyophenyl


combination of



710



substituents







corresponding







to each row of







Table B
















TABLE 14







Table A













Compound







No.
Ar
A
Y
R
















Table
417-
Phenyl
A-10
H
represents a


417
1~417-



combination of



710



substituents







corresponding to







each row of







Table B


Table
418-
cyclopentyl
A-11
H
represents a


418
1~418-



combination of



710



substituents







corresponding to







each row of







Table B


Table
419-
cyclohexyl
A-12
H
represents a


419
1~419-



combination of



710



substituents







corresponding to







each row of







Table B


Table
420-
3-
A-17
H
represents a


420
1~420-
methyl-


combination of



710
cyclohexyl


substituents







corresponding to







each row of







Table B


Table
421-
cyclobutyl
A-18
H
represents a


421
1~421-



combination of



710



substituents







corresponding to







each row of







Table B


Table
422-
2-oxetanyl
A-19
H
represents a


422
1~422-



combination of



710



substituents







corresponding to







each row of







Table B


Table
423-
3-oxetanyl
A-20
H
represents a


423
1~423-



combination of



710



substituents







corresponding to







each row of







Table B


Table
424-
2-thietanyl
A-21
H
represents a


424
1~424-



combination of



710



substituents







corresponding to







each row of







Table B


Table
425-
3-thietanyl
A-22
H
represents a


425
1~425-



combination of



710



substituents







corresponding to







each row of







Table B


Table
426-
2-azetidinyl
A-23
H
represents a


426
1~426-



combination of



710



substituents







corresponding to







each row of







Table B


Table
427-
3-azetidinyl
A-24
H
represents a


427
1~427-



combination of



710



substituents







corresponding to







each row of







Table B


Table
428-
6-iodo-3-
A-25
H
represents a


428
1~428-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
429-
6-iodo-
A-26
H
represents a


429
1~429-
3-pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
430-
2-
A-27
H
represents a


430
1~430-
tetrahydrofu-


combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
431-
2-Chloro-3-
A-28
H
represents a


431
1~431-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
432-
5-Chloro-3-
A-29
H
represents a


432
1~432-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
433-
6-Chloro-3-
A-30
H
represents a


433
1~433-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
434-
4-Chloro-3-
A-31
H
represents a


434
1~434-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
435-
2-Chloro-4-
A-32
H
represents a


435
1~435-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
436-
3-Chloro-4-
A-33
H
represents a


436
1~436-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
437-
3-bromo-2-
A-34
H
represents a


437
1~437-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
438-
4-bromo-2-
A-35
H
represents a


438
1~438-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
439-
2-FIuoro-4-
A-36
H
represents a


439
1~439-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
440-
3-Fluoro-4-
A-37
H
represents a


440
1~440-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
441-
6-Fluoro-3-
A-38
H
represents a


441
1~441-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
442-
3-iodo-
A-39
H
represents a


442
1~442-
2-pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
443-
6-Fluoro-3-
A-40
H
represents a


443
1~443-
pyridyl


combination of



710



substituents







corresponding to







each row of







Table B


Table
444-
2-Chloro-5-
A-38
H
represents a


444
1~444-
thiazolyl


combination of



710



substituents







corresponding to







each row of







Table B
















TABLE 15







Table A













Compound







No.
Ar
A
Y
R
















Table
445-
6-Chloro-3-
A-1
3-
represents a


445
1~445-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
446-
2-Chloro-5-
A-1
3-
represents a


446
1~446-
thiazolyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
447-
6-Fluoro-3-
A-1
3-
represents a


447
1~447-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
448-
6-Bromo-3-
A-1
3-
represents a


448
1~448-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
449-
6-Chloro-5-
A-1
3-
represents a


449
1~449-
fluoro-3-

CH3
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
450-
2-Chloro-5-
A-1
3-
represents a


450
1~450-
pyrimidinyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
451-
5-
A-1
3-
represents a


451
1~451-
Chloropyrazin-

CH3
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
452-
6-
A-1
3-
represents a


452
1~452-
Chloropyridazin-

CH3
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
453-
2-Chloro-5-
A-1
3-
represents a


453
1~453-
oxazolyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
454-
6-
A-1
3-
represents a


454
1~454-
trifluoromethyl-

CH3
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
455-
3-
A-1
3-
represents a


455
1~455-
tetrahydrofu-

CH3
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
456-
6-Chloro-3-
A-1
4-
represents a


456
1~456-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
457-
2-Chloro-5-
A-1
4-
represents a


457
1~457-
thiazolyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
458-
6-Fluoro-3-
A-1
4-
represents a


458
1~458-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
459-
6-Bromo-3-
A-1
4-
represents a


459
1~459-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
460-
6-Chloro-5-
A-1
4-
represents a


460
1~460-
Fluoro-3-

CH3
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
461-
2-Chloro-5-
A-1
4-
represents a


461
1~461-
pyrimidinyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
462-
5-
A-1
4-
represents a


462
1~462-
Chloropyrazin-

CH3
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
463-
6-
A-1
4-
represents a


463
1~463-
Chloropyridazin-

CH3
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
464-
2-Chloro-5-
A-1
4-
represents a


464
1~464-
oxazolyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
465-
6-
A-1
4-
represents a


465
1~465-
trifluoromethyl-

CH3
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
466-
3-
A-1
4-
represents a


466
1~466-
tetrahydrofu-

CH3
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
467-
6-Chloro-3-
A-1
5-
represents a


467
1~467-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
468-
2-Chloro-5-
A-1
5-
represents a


468
1~468-
thiazolyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
469-
6-Fluoro-3-
A-1
5-
represents a


469
1~469-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
470-
6-Bromo-3-
A-1
5-
represents a


470
1~470-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
471-
6-Chloro-5-
A-1
5-
represents a


471
1~471-
fluoro-3-

CH3
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
472-
2-Chloro-5-
A-1
5-
represents a


472
1~472-
pyrimidinyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
473-
5-
A-1
5-
represents a


473
1~473-
Chloropyrazin-

CH3
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
474-
6-
A-1
5-
represents a


474
1~474-
Chloropyridazin-

CH3
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
475-
2-Chloro-5-
A-1
5-
represents a


475
1~475-
oxazolyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
476-
6-
A-1
5-
represents a


476
1~476-
trifluoromethyl-

CH3
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B
















TABLE 16







Table A













Compound







No.
Ar
A
Y
R
















Table
477-
3-
A-1
5-
represents a


477
1~477-
tetrahydrofu-

CH3
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
478-
6-Chloro-3-
A-1
6-
represents a


478
1~478-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
479-
2-Chloro-5-
A-1
6-
represents a


479
1~479-
thiazolyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
480-
6-Fluoro-3-
A-1
6-
represents a


480
1~480-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
481-
6-Bromo-3-
A-1
6-
represents a


481
1~481-
pyridyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
482-
6-Chloro-5-
A-1
6-
represents a


482
1~482-
fluoro-3-

CH3
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
483-
2-Chloro-5-
A-1
6-
represents a


483
1~483-
pyrimidinyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
484-
5-
A-1
6-
represents a


484
1~484-
Chloropyrazin-

CH3
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
485-
6-
A-1
6-
represents a


485
1~485-
Chloropyridazin-

CH3
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
486-
2-Chloro-5-
A-1
6-
represents a


486
1~486-
oxazolyl

CH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
487-
6-
A-1
6-
represents a


487
1~487-
trifluoromethyl-

CH3
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
488-
3-
A-1
6-
represents a


488
1~488-
tetrahydrofu-

CH3
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
489-
6-Chloro-3-
A-1
3-
represents a


489
1~489-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
490-
2-Chloro-5-
A-1
3-
represents a


490
1~490-
thiazolyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
491-
6-Fluoro-3-
A-1
3-
represents a


491
1~491-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
492-
6-Bromo-
A-1
3-
represents a


492
1~492-
3-pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
493-
6-Chloro-5-
A-1
3-
represents a


493
1~493-
Fluoro-3-

NO2
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
494-
2-Chloro-5-
A-1
3-
represents a


494
1~494-
pyrimidinyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
495-
5-
A-1
3-
represents a


495
1~495-
Chloropyrazin-

NO2
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
496-
6-
A-1
3-
represents a


496
1~496-
Chloropyridazin-

NO2
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
497-
2-Chloro-5-
A-1
3-
represents a


497
1~497-
oxazolyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
498-
6-
A-1
3-
represents a


498
1~498-
trifluoromethyl-

NO2
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
499-
3-
A-1
3-
represents a


499
1~499-
tetrahydrofu-

NO2
combination of



710
ranyl


substituents







corresponding to







each row of







Table B


Table
500-
6-Chloro-3-
A-1
4-
represents a


500
1~500-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
501-
2-Chloro-5-
A-1
4-
represents a


501
1~501-
thiazolyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
502-
6-Fluoro-3-
A-1
4-
represents a


502
1~502-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
503-
6-Bromo-3-
A-1
4-
represents a


503
1~503-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
504-
6-Chloro-5-
A-1
4-
represents a


504
1~504-
fluoro-3-

NO2
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
505-
2-Chloro-5-
A-1
4-
represents a


505
1~505-
pyrimidinyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
506-
5-
A-1
4-
represents a


506
1~506-
Chloropyrazin-

NO2
combination of



710
2-yl


substituents







corresponding to







each row of







Table B


Table
507-
6-
A-1
4-
represents a


507
1~507-
Chloropyridazin-

NO2
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
508-
2-Chloro-5-
A-1
4-
represents a


508
1~508-
oxazolyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B
















TABLE 17







Table A













Compound







No.
Ar
A
Y
R
















Table
509~
6-tri-
A-1
4-
represents a


509
1~509-
fluoromethyl-

NO2
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
510-
3-
A-1
4-
represents a


510
1~510-
tetrahydro-

NO2
combination of



710
furanyl


substituents







corresponding to







each row of







Table B


Table
511-
6-Chloro-3-
A-1
5-
represents a


511
1~511-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
512-
2-Chloro-5-
A-1
5-
represents a


512
1~512-
thiazolyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
513-
6-Fluoro-3-
A-1
5-
represents a


513
1~513-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
514-
6-Bromo-3-
A-1
5-
represents a


514
1~514-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
515-
6-Chloro-5-
A-1
5-
represents a


515
1~515-
fluoro-3-

NO2
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
516-
2-Chloro-5-
A-1
5-
represents a


516
1~516-
pyrimidinyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
517-
5-Chloro-
A-1
5-
represents a


517
1~517-
pyrazin-2-yl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
518-
6-Chloro-
A-1
5-
represents a


518
1~518-
pyridazin-

NO2
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
519-
2-Chloro-5-
A-1
5-
represents a


519
1~519-
oxazolyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
520-
6-tri-
A-1
5-
represents a


520
1~520-
fluoromethyl-

NO2
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
521-
3-tetrahydro-
A-1
5-
represents a


521
1~521-
furanyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
522-
6-Chloro-3-
A-1
6-
represents a


522
1~522-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
523-
2-Chloro-5-
A-1
6-
represents a


523
1~523-
thiazolyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
524-
6-Fluoro-3-
A-1
6-
represents a


524
1~524-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
525-
6-Bromo-3-
A-1
6-
represents a


525
1~525-
pyridyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
526-
6-Chloro-5-
A-1
6-
represents a


526
1~526-
Fluoro-3-

NO2
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
527-
2-Chloro-5-
A-1
6-
represents a


527
1~527-
pyrimidinyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
528-
5-Chloro-
A-1
6-
represents a


528
1~528-
pyrazin-2-yl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
529-
6-Chloro-
A-1
6-
represents a


529
1~529-
pyridazin-

NO2
combination of



710
3-yl


substituents







corresponding to







each row of







Table B


Table
530-
2-Chloro-5-
A-1
6-
represents a


530
1~530-
oxazolyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
531-
6-tri-
A-1
6-
represents a


531
1~531-
fluoromethyl-

NO2
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
532-
3-tetra-
A-1
6-
represents a


532
1~532-
hydrofuranyl

NO2
combination of



710



substituents







corresponding to







each row of







Table B


Table
533-
6-Chloro-3-
A-1
3-
represents a


533
1~533-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
534-
2-Chloro-5-
A-1
3-
represents a


534
1~534-
thiazolyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
535-
6-Fluoro-3-
A-1
3-
represents a


535
1~535-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
536-
6-Bromo-3-
A-1
3-
represents a


536
1~536-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
537-
6-Chloro-5-
A-1
3-
represents a


537
1~537-
fluoro-3-

OCH3
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
538-
2-Chloro-5-
A-1
3-
represents a


538
1~538-
pyrimidinyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
539-
5-Chloro-
A-1
3-
represents a


539
1~539-
pyrazin-2-yl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
540-
6-Chloro-
A-1
3-
represents a


540
1~540-
pyridazin-3-yl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B
















TABLE 18







Table A













Compound







No.
Ar
A
Y
R
















Table
541-
2-Chloro-5-
A-1
3-
represents a


541
1~541-
oxazolyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
542-
6-tri-
A-1
3-
represents a


542
1~542-
fluoromethyl-

OCH3
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
543-
3-tetra-
A-1
3-
represents a


543
1~543-
hydrofuranyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
544-
6-Chloro-3-
A-1
4-
represents a


544
1~544-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
545-
2-Chloro-5-
A-1
4-
represents a


545
1~545-
thiazolyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
546-
6-Fluoro-3-
A-1
4-
represents a


546
1~546-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
547-
6-Bromo-3-
A-1
4-
represents a


547
1~547-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
548-
6-Chloro-5-
A-1
4-
represents a


548
1~548-
Fluoro-3-

OCH3
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
549-
2-Chloro-5-
A-1
4-
represents a


549
1~549-
pyrimidinyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
550-
5-Chloro-
A-1
4-
represents a


550
1~550-
pyrazin-2-yl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
551-
6-Chloro-
A-1
4-
represents a


551
1~551-
pyridazin-3-yl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
552-
2-Chloro-5-
A-1
4-
represents a


552
1~552-
oxazolyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
553-
6-tri-
A-1
4-
represents a


553
1~553-
fluoromethyl-

OCH3
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
554-
3-tetra-
A-1
4-
represents a


554
1~554-
hydrofuranyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
555-
6-Chloro-3-
A-1
5-
represents a


555
1~555-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
556-
2-Chloro-5-
A-1
5-
represents a


556
1~556-
thiazolyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
557-
6-Fluoro-3-
A-1
5-
represents a


557
1~557-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
558-
6-Bromo-3-
A-1
5-
represents a


558
1~558-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
559-
6-Chloro-5-
A-1
5-
represents a


559
1~559-
fluoro-3-

OCH3
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
560-
2-Chloro-5-
A-1
5-
represents a


560
1~560-
pyrimidinyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
561-
5-Chloro-
A-1
5-
represents a


561
1~561-
pyrazin-2-yl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
562-
6-Chloro-
A-1
5-
represents a


562
1~562-
pyridazin-3-yl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
563-
2-Chloro-5-
A-1
5-
represents a


563
1~563-
oxazolyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
564-
6-tri-
A-1
5-
represents a


564
1~564-
fluoromethyl-

OCH3
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
565-
3-tetra-
A-1
5-
represents a


565
1~565-
hydrofuranyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
566-
6-Chloro-3-
A-1
6-
represents a


566
1~566-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
567-
2-Chloro-5-
A-1
6-
represents a


567
1~567-
thiazolyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
568-
6-Fluoro-3-
A-1
6-
represents a


568
1~568-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
569-
6-Bromo-3-
A-1
6-
represents a


569
1~569-
pyridyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
570-
6-Chloro-5-
A-1
6-
represents a


570
1~570-
Fluoro-3-

OCH3
combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
571-
2-Chloro-5-
A-1
6-
represents a


571
1~571-
pyrimidinyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
572-
5-Chloro-
A-1
6-
represents a


572
1~572-
pyrazin-2-yl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B
















TABLE 19







Table A













Compound







No.
Ar
A
Y
R
















Table
573-
6-Chloro-
A-1
6-
represents a


573
1~573-
pyridazin-3-yl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
574-
2-Chloro-5-
A-1
6-
represents a


574
1~574-
oxazolyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
575-
6-tri-
A-1
6-
represents a


575
1~575-
fluoromethyl-

OCH3
combination of



710
3-pyridyl


substituents







corresponding to







each row of







Table B


Table
576-
3-tetra-
A-1
6-
represents a


576
1~576-
hydrofuranyl

OCH3
combination of



710



substituents







corresponding to







each row of







Table B


Table
577-
2,6-
A-1
H
represents a


577
1~577-
dichloro-3-


combination of



710
pyridyl


substituents







corresponding to







each row of







Table B


Table
578-
3-pyridyl
A-1
H
represents a


578
1~578-



combination of



710



substituents







corresponding to







each row of







Table B


Table
579-
4-pyridyl
A-1
H
represents a


579
1~579-



combination of



710



substituents







corresponding to







each row of







Table B


Table
580-
6-chloro-3-
A-1
H
represents a


580
1~580-
pyridyl-N-


combination of



710
oxide


substituents







corresponding to







each row of







Table B



















TABLE B








R

























R1







1

H



2

CF3



3

CHF2



4

CF2Cl



5

CF2CF3



6

CH2Cl



7

CHCl2



8

CCl3



9

CHClBr



10

2,2-





difluorocyclopropyl



11

2,3,3-





trifluoroacryl



12

CH2CHF2



13

CH2CF3



14

CH═CH2



15

CH2C≡CH



16

CH2CH2C≡CH












R2







17

CH2CF3



18

CH(Me)CF3



19

CH(CF3)2












R3







20

CF3



21

CHF2



22

CF2Cl



23

CF2CF3



24

CH2Cl



25

CHCl2



26

CCl3



27

CHClBr



28

CHBr2



29

2,3,3-





trifluoroacryl



30

CH2CHF2



31

CH2CF3



32

CH═CH2



33

CH2C≡CH



34

CH2CF3



35

CH2CH2Ph



36

Me



37

Et



38

n-Pr



39

i-Pr



40

cyclopropyl




















TABLE B










R











 












R4
R5







41
H
CF3



42
Me
CF3



43
Et
CF3



44
n-Pr
CF3



45
i-Pr
CF3



46
t-Bu
CF3



47
n-Bu
CF3



48
n-Pentyl
CF3



49
n-Hexyl
CF3



50
cyclopropyl
CF3



51
cyclobutyl
CF3



52
cyclopentyl
CF3



53
cyclohexyl
CF3



54
CH═CH2
CF3



55
CH2CH═CH2
CF3



56
CH2C≡CH
CF3



57
CH2CH2CΞCH
CF3



58
CH2CHF2
CF3



59
CH2CCF3
CF3



60
CH2CH2Cl
CF3



61
CH2CHCl2
CF3



62
2-fluoro-2-
CF3




chloroethyl




63
CH2CCl3
CF3



64
CH2CN
CF3



65
CH2CH2CN
CF3



66
CH2CH(CN)CH2CN
CF3



67
CH2CH2OH
CF3



68
CH2CH2CH2OH
CF3



69
CH2CH(OH)CH2OH
CF3



70
CH2CH2NO2
CF3



71
Phenyl
CF3



72
CH2-Phenyl
CF3



73
CH(Me)-Phenyl
CF3



74
C(Me2)-Phenyl
CF3



75
C(cyclopropyl)-Phenyl
CF3



76
CH2CH2-Phenyl 
CF3



77
CH2-(2-
CF3




Methylphenyl)




78
CH2-(3-
CF3




Methylphenyl)




79
CH2-(4-
CF3




Methylphenyl)




80
CH2-(2-
CF3




Methoxylphenyl)




81
CH2-(3-
CF3




Methoxylphenyl)




82
CH2-(4-
CF3




Methoxylphenyl)




83
CH2-(2-
CF3




fluorolphenyl)




84
CH2-(3-
CF3




fluorolphenyl)




85
CH2-(4-
CF3




fluorolphenyl)




86
CH2-(2-
CF3




Chlorophenyl)




87
CH2-(3-
CF3




Chlorophenyl)




88
CH2-(4-
CF3




Chlorophenyl)




89
CH2-(2-
CF3




Bromophenyl)




90
CH2-(3-
CF3




Bromophenyl)




91
CH2-(4-
CF3




Bromophenyl)




92
CH2-(2-
CF3




iodophenyl)




93
CH2-(3-
CF3




iodophenyl)




















TABLE B










R



 




















R4
R5







 94
CH2-(4-iodophenyl)
CF3



 95
CH2-(1-naphthalenyl)
CF3



 96
CH2-(2-naphthalenyl)
CF3



 97
naphthalen-1-ylmethyl
CF3



 98
naphthalen-2-ylmethyl
CF3



 99
quinolin-2-ylmethyl
CF3



100
quinolin-7-ylmethyl
CF3



101
isoquinolin-7-ylmethyl
CF3



102
isoquinolin-6-ylmethyl 
CF3



103
quinolin-6-ylmethyl
CF3



104
quinolin-3-ylmethyl
CF3



105
isoquinolin-3-ylmethyl
CF3



106
isoquinolin-1-ylmethyl
CF3



107
isoquinolin-4-ylmethyl
CF3



108
quinolin-4-ylmethyl
CF3



109
quinolin-5-ylmethyl
CF3



110
isoquinolin-5-ylmethyl
CF3



111
isoquinolin-8-ylmethyl
CF3



112
quinolin-8-ylmethyl
CF3



113
CH2O-Phenyl
CF3



114
CH2CH2O-Phenyl
CF3



115
2-pyridyl
CF3



116
3-pyridyl
CF3



117
4-pyridyl
CF3



118
CH2-(2-pyridyl)
CF3



119
CH2-(3-pyridyl)
CF3



120
CH2-(4-Chloro-3-pyridyl)
CF3



121
CH2-(4-pyridyl)
CF3



122
CH2-(2-thienyl)
CF3



123
CH2-(3-thienyl)
CF3



124
CH2-(2-furanyl)
CF3



125
CH2-(3-furanyl)
CF3



126
CH2-(2-tetrahydrofuranyl)
CF3



127
CH2-(3-tetrahydrofuranyl)
CF3



128
(1H-imidazol-2-yl)methyl
CF3



129
(1H-imidazol-1-yl)methyl
CF3



130
(1H-imidazol-4-yl)methyl
CF3



131
CH2-(2-thiazolyl)
CF3



132
CH2-(3-thiazolyl)
CF3



133
CH2-(2-pyrrolyl)
CF3



134
CH2-(3-pyrrolyl)
CF3



135
CH2-(5-methylpyrazol-1-yl)
CF3



136
CH2-(1-pyrazolyl)
CF3



137
CH2-(2-pyrazolyl)
CF3



138
CH2-(3-pyrazolyl)
CF3



139
CH2-(4-pyrazolyl)
CF3



140
CH2-(5-pyrazolyl)
CF3



141
CH2-(2-oxazolyl)
CF3



142
CH2-(3-oxazolyl)
CF3



143
CH2-(3-isoxazolyl)
CF3



144
CH2-(4-isoxazolyl)
CF3



145
CH2-(5-isoxazolyl)
CF3



146
CH2CH2OCH3
CF3



147
CH2CH2OCH2CH3
CF3




















TABLE B










R



 




















R4
R5







148
CH2CH2CH2OCH3
CF3



149
CH2CH2CH2OCH2CH3
CF3



150
CH2CH2SCH3
CF3



151
CH2CH2SCH2CH3
CF3



152
CH2CH2CH2SCH3
CF3



153
CH2CH2CH2SCH2CH3
CF3



154
Me
CHF2



155
Et
CHF2



156
n-Pr
CHF2



157
i-Pr
CHF2



158
t-Bu
CHF2



159
n-Bu
CHF2



160
n-Pentyl
CHF2



161
n-Hexyl
CHF2



162
cyclopropyl
CHF2



163
cyclobutyl
CHF2



164
cyclopentyl
CHF2



165
cyclohexyl
CHF2



166
CH═CH2
CHF2



167
CH2CH═CH2
CHF2



168
CH2C≡CH
CHF2



169
CH2CH2C≡CH
CHF2



170
CH2CHF2
CHF2



171
CH2CCF3
CHF2



172
CH2CH2Cl
CHF2



173
CH2CHCl2
CHF2



174
2-fluoro-2-chloroethyl
CHF2



175
CH2CCl3
CHF2



176
CH2CH2CN
CHF2



177
CH2CH2CH2CN
CHF2



178
CH2CH(CN)CH2CN
CHF2



179
CH2CH2OH
CHF2



180
CH2CH2CH2OH
CHF2



181
CH2CH(OH)CH2OH 
CHF2



182
CH2CH2NO2
CHF2



183
Phenyl
CHF2



184
CH2-Phenyl
CHF2



185
CH(Me)-Phenyl
CHF2



186
C(Me2)-Phenyl
CHF2



187
C(cyclopropyl)-Phenyl
CHF2



188
CH2CH2-Phenyl
CHF2



189
CH2-(2-Methylphenyl)
CHF2



190
CH2-(3-Methylphenyl)
CHF2



191
CH2-(4-Methylphenyl)
CHF2



192
CH2-(2-Methoxylphenyl)
CHF2



193
CH2-(3-Methoxylphenyl)
CHF2



194
CH2-(4-Methoxylphenyl)
CHF2



195
CH2-(2-fluorolphenyl)
CHF2



196
CH2-(3-fluorolphenyl)
CHF2



197
CH2-(4-fluorolphenyl)
CHF2



198
CH2-(2-Chlorophenyl)
CHF2



199
CH2-(3-Chlorophenyl)
CHF2



200
CH2-(4-Chlorophenyl)
CHF2



201
CH2-(2-Bromophenyl)
CHF2




















TABLE B










R



 




















R4
R5







202
CH2-(3-Bromophenyl)
CHF2



203
CH2-(4-Bromophenyl)
CHF2



204
CH2-(2-iodophenyl)
CHF2



205
CH2-(3-iodophenyl)
CHF2



206
CH2-(4-iodophenyl)
CHF2



207
CH2-(1-naphthalenyl)
CHF2



208
CH2-(2-naphthalenyl)
CHF2



209
naphthalen-1-ylmethyl
CHF2



210
naphthalen-2-ylmethyl
CHF2



211
quinolin-2-ylmethyl
CHF2



212
quinolin-7-ylmethyl
CHF2



213
isoquinolin-7-ylmethyl
CHF2



214
isoquinolin-6-ylmethyl
CHF2



215
quinolin-6-ylmethyl
CHF2



216
quinolin-3-ylmethyl
CHF2



217
isoquinolin-3-ylmethyl
CHF2



218
isoquinolin-1-ylmethyl
CHF2



219
isoquinolin-4-ylmethyl
CHF2



220
quinolin-4-ylmethyl
CHF2



221
quinolin-5-ylmethyl
CHF2



222
isoquinolin-5-ylmethyl
CHF2



223
isoquinolin-8-ylmethyl
CHF2



224
quinolin-8-ylmethyl
CHF2



225
CH2O-Phenyl
CHF2



226
CH2CH2O-Phenyl
CHF2



227
2-pyridyl
CHF2



228
3-pyridyl
CHF2



229
4-pyridyl
CHF2



230
CH2-(2-pyridyl)
CHF2



231
CH2-(3-pyridyl)
CHF2



232
CH2-(4-Chloro-3-pyridyl)
CHF2



233
CH2-(4-pyridyl)
CHF2



234
CH2-(2-thienyl)
CHF2



235
CH2-(3-thienyl)
CHF2



236
CH2-(2-furanyl)
CHF2



237
CH2-(3-furanyl)
CHF2



238
CH2-(2-tetrahydrofuranyl)
CHF2



239
CH2-(3-tetrahydrofurany1)
CHF2



240
(1H-imidazol-2-yl)methyl
CHF2



241
(1H-imidazol-1-yl)methyl
CHF2



242
(1H-imidazol-4-yl)methyl
CHF2



243
CH2-(2-thiazolyl)
CHF2



244
CH2-(3-thiazolyl)
CHF2



245
CH2-(2-pyrrolyl)
CHF2



246
CH2-(3-pyrrolyl)
CHF2



247
CH2-(5-methylpyrazol-1-yl)
CHF2



248
CH2-(1-pyrazolyl)
CHF2



249
CH2-(2-pyrazolyl)
CHF2



250
CH2-(3-pyrazolyl)
CHF2



251
CH2-(4-pyrazolyl)
CHF2



252
CH2-(5-pyrazolyl)
CHF2



253
CH2-(2-oxazolyl)
CHF2



254
CH2-(3-oxazolyl
CHF2



255
CH2-(3-isoxazolyl)
CHF2




















TABLE B










R



 




















R4
R5







256
CH2-(4-isoxazolyl)
CHF2



257
CH2-(5-isoxazolyl)
CHF2



258
CH2CH2OCH3
CHF2



259
CH2CH2OCH2CH3
CHF2



260
CH2CH2CH2OCH3
CHF2



261
CH2CH2CH2OCH2CH3
CHF2



262
CH2CH2SCH3
CHF2



263
CH2CH2SCH2CH3
CHF2



264
CH2CH2CH2SCH3
CHF2



265
CH2CH2CH2SCH2CH3
CHF2



266
Me
CF2Cl



267
Et
CF2Cl



268
n-Pr
CF2Cl



269
i-Pr
CF2Cl



270
t-Bu
CF2Cl



271
n-Bu
CF2Cl



272
n-Pentyl
CF2Cl



273
n-Hexyl
CF2Cl



274
cyclopropyl
CF2Cl



275
cyclobutyl
CF2Cl



276
cyclopentyl
CF2Cl



277
cyclohexyl
CF2Cl



278
CH═CH2
CF2Cl



279
CH2CH═CH2
CF2Cl



280
CH2C≡CH
CF2Cl



281
CH2CH2C≡CH
CF2Cl



282
CH2CHF2
CF2Cl



283
CH2CCF3
CF2Cl



284
CH2CH2Cl
CF2Cl



285
CH2CHCl2
CF2Cl



286
2-fluoro-2-chloroethyl
CF2Cl



287
CH2CCl3
CF2Cl



288
CH2CH2CN
CF2Cl



289
CH2CH2CH2CN
CF2Cl



290
CH2CH(CN)CH2CN
CF2Cl



291
CH2CH2OH
CF2Cl



292
CH2CH2CH2OH
CF2Cl



293
CH2CH(OH)CH2OH
CF2Cl



294
CH2CH2NO2
CF2Cl



295
Phenyl
CF2Cl



296
CH2-Phenyl
CF2Cl



297
CH(Me)-Phenyl
CF2Cl



298
C(Me2)-Phenyl
CF2Cl



299
C(cyclopropyl)-Phenyl
CF2Cl



300
CH2CH2-Phenyl
CF2Cl



301
CH2-(2-Methylphenyl)
CF2Cl



302
CH2-(3-Methylphenyl)
CF2Cl



303
CH2-(4-Methylphenyl)
CF2Cl



304
CH2-(2-Methoxylphenyl)
CF2Cl



305
CH2-(3-Methoxylphenyl)
CF2Cl



306
CH2-(4-Methoxylphenyl)
CF2Cl



307
CH2-(2-fluorolphenyl)
CF2Cl



308
CH2-(3-fluorolphenyl)
CF2Cl



309
CH2-(4-fluorolphenyl)
CF2Cl




















TABLE B










R



 




















R4
R5







310
CH2-(2-Chlorophenyl)
CF2Cl



311
CH2-(3-Chlorophenyl)
CF2Cl



312
CH2-(4-Chlorophenyl)
CF2Cl



313
CH2-(2-Bromophenyl)
CF2Cl



314
CH2-(3-Bromophenyl)
CF2Cl



315
CH2-(4-Bromophenyl) 
CF2Cl



316
CH2-(2-iodophenyl)
CF2Cl



317
CH2-(3-iodophenyl)
CF2Cl



318
CH2-(4-iodophenyl)
CF2Cl



319
CH2-(1-naphthalenyl)
CF2Cl



320
CH2-(2-naphthalenyl)
CF2Cl



321
naphthalen-1-ylmethyl
CF2Cl



322
naphthalen-2-ylmethyl
CF2Cl



323
quinolin-2-ylmethyl
CF2Cl



324
quinolin-7-ylmethyl
CF2Cl



325
isoquinolin-7-ylmethyl
CF2Cl



326
isoquinolin-6-ylmethyl
CF2Cl



327
quinolin-6-ylmethyl
CF2Cl



328
quinolin-3-ylmethyl
CF2Cl



329
isoquinolin-3-ylmethyl
CF2Cl



330
isoquinolin-1-ylmethyl
CF2Cl



331
isoquinolin-4-ylmethyl 
CF2Cl



332
quinolin-4-ylmethyl
CF2Cl



333
quinolin-5-ylmethyl
CF2Cl



334
isoquinolin-5-ylmethyl
CF2Cl



335
isoquinolin-8-ylmethyl
CF2Cl



336
quinolin-8-ylmethyl
CF2Cl



337
CH2O-Phenyl
CF2Cl



338
CH2CH2O-Phenyl
CF2Cl



339
2-pyridyl
CF2Cl



340
3-pyridyl
CF2Cl



341
4-pyridyl
CF2Cl



342
CH2-(2-pyridyl)
CF2Cl



343
CH2-(3-pyridyl)
CF2Cl



344
CH2-(4-Chloro-3-pyridyl)
CF2Cl



345
CH2-(4-pyridyl)
CF2Cl



346
CH2-(2-thienyl)
CF2Cl



347
CH2-(3-thienyl)
CF2Cl



348
CH2-(2-furanyl)
CF2Cl



349
CH2-(3-furanyl)
CF2Cl



350
CH2-(2-tetrahydrofuranyl)
CF2Cl



351
CH2-(3-tetrahydrofuranyl)
CF2Cl



352
(1H-imidazol-2-yl)methyl
CF2Cl



353
(1H-imidazol-1-yl)methyl
CF2Cl



354
(1H-imidazol-4-yl)methyl
CF2Cl



355
CH2-(2-thiazolyl)
CF2Cl



356
CH2-(3-thiazolyl)
CF2Cl



357
CH2-(2-pyrrolyl)
CF2Cl



358
CH2-(3-pyrrolyl)
CF2Cl



359
CH2-(1-pyrazolyl)
CF2Cl



360
CH2-(2-pyrazolyl)
CF2Cl



361
CH2-(3-pyrazolyl)
CF2Cl



362
CH2-(4-pyrazolyl)
CF2Cl



363
CH2-(5-pyrazolyl)
CF2Cl




















TABLE B










R



 




















R4
R5







364
CH2-(5-pyrazolyl)
CF2Cl



365
CH2-(2-oxazolyl)
CF2Cl



366
CH2-(3-oxazolyl)
CF2Cl



367
CH2-(3-isoxazolyl)
CF2Cl



368
CH2-(4-isoxazolyl)
CF2Cl



369
CH2-(5-isoxazolyl)
CF2Cl



370
CH2CH2OCH3
CF2Cl



371
CH2CH2OCH2CH3
CF2Cl



372
CH2CH2CH2OCH3
CF2Cl



373
CH2CH2CH2OCH2CH3
CF2Cl



374
CH2CH2SCH3
CF2Cl



375
CH2CH2SCH2CH3
CF2Cl



376
CH2CH2CH2SCH3
CF2Cl



377
CH2CH2CH2SCH2CH3
CF2Cl



378
Me
CF2CF3



379
Et
CF2CF3



380
n-Pr
CF2CF3



381
i-Pr
CF2CF3



382
t-Bu
CF2CF3



383
n-Bu
CF2CF3



384
n-Pentyl
CF2CF3



385
n-Hexyl
CF2CF3



386
cyclopropyl
CF2CF3



387
cyclobutyl
CF2CF3



388
cyclopentyl
CF2CF3



389
cyclohexyl
CF2CF3



390
CH═CH2
CF2CF3



391
CH2CH═CH2
CF2CF3



392
CH2C≡CH
CF2CF3



393
CH2CH2C≡CH
CF2CF3



394
CH2CHF2
CF2CF3



395
CH2CCF3
CF2CF3



396
CH2CH2Cl
CF2CF3



397
CH2CHCl2
CF2CF3



398
2-fluoro-2-chloroethyl
CF2CF3



399
CH2CCl3
CF2CF3



400
CH2CH2CN
CF2CF3



401
CH2CH2CH2CN
CF2CF3



402
CH2CH(CN)CH2CN
CF2CF3



403
CH2CH2OH
CF2CF3



404
CH2CH2CH2OH
CF2CF3



405
CH2CH(OH)CH2OH
CF2CF3



406
CH2CH2NO2
CF2CF3



407
Phenyl
CF2CF3



408
CH2-Phenyl
CF2CF3



409
CH(Me)-Phenyl
CF2CF3



410
C(Me2)-Phenyl
CF2CF3



411
C(cyclopropyl)-Phenyl
CF2CF3



412
CH2CH2-Phenyl
CF2CF3



413
CH2-(2-Methylphenyl)
CF2CF3



414
CH2-(3-Methylphenyl)
CF2CF3



415
CH2-(4-Methylphenyl)
CF2CF3



416
CH2-(2-Methoxylphenyl)
CF2CF3



417
CH2-(3-Methoxylphenyl)
CF2CF3


















TABLE B








R


 

















R4
R5





418
CH2-(4-Methoxylphenyl)
CF2CF3


419
CH2-(2-fluorolphenyl)
CF2CF3


420
CH2-(3-fluorolphenyl)
CF2CF3


421
CH2-(4-fluorolphenyl)
CF2CF3


422
CH2-(2-Chlorophenyl)
CF2CF3


423
CH2-(3-Chlorophenyl)
CF2CF3


424
CH2-(4-Chlorophenyl)
CF2CF3


425
CH2-(2-Bromophenyl)
CF2CF3


426
CH2-(3-Bromophenyl)
CF2CF3


427
CH2-(4-Bromophenyl)
CF2CF3


428
CH2-(2-iodophenyl)
CF2CF3


429
CH2-(3-iodophenyl)
CF2CF3


430
CH2-(4-iodophenyl)
CF2CF3


431
CH2-(1-naphthalenyl)
CF2CF3


432
CH2-(2-naphthalenyl)
CF2CF3


433
naphthalen-1-ylmethyl
CF2CF3


434
naphthalen-2-ylmethyl
CF2CF3


435
quinolin-2-ylmethyl
CF2CF3


436
quinolin-7-ylmethyl
CF2CF3


437
isoquinolin-7-ylmethyl
CF2CF3


438
isoquinolin-6-ylmethyl
CF2CF3


439
quinolin-6-ylmethyl
CF2CF3


440
quinolin-3-ylmethyl
CF2CF3


441
isoquinolin-3-ylmethyl
CF2CF3


442
isoquinolin-1-ylmethyl
CF2CF3


443
isoquinolin-4-ylmethyl
CF2CF3


444
quinolin-4-ylmethyl
CF2CF3


445
quinolin-5-ylmethyl
CF2CF3


446
isoquinolin-5-ylmethyI
CF2CF3


447
isoquinolin-8-ylmethyl
CF2CF3


448
quinolin-8-ylmethyl
CF2CF3


449
CH2O-Phenyl
CF2CF3


450
CH2CH2O-Phenyl
CF2CF3


451
2-pyridyl
CF2CF3


452
3-pyridyl
CF2CF3


453
4-pyridyl
CF2CF3


454
CH2-(2-pyridyl)
CF2CF3


455
CH2-(3-pyridyl)
CF2CF3


456
CH2-(4-Chloro-3-pyridyl)
CF2CF3


457
CH2-(4-pyridyl)
CF2CF3


458
CH2-(2-thienyl)
CF2CF3


459
CH2-(3-thienyl)
CF2CF3


460
CH2-(2-furanyl)
CF2CF3


461
CH2-(3-furanyl)
CF2CF3


462
CH2-(2-tetrahydrofuranyl)
CF2CF3


463
CH2-(3-tetrahydrofuranyl)
CF2CF3


464
(1H-imidazol-2-yl)methyl
CF2CF3


465
(1H-imidazol-1-yImethyl
CF2CF3


466
(1H-imidazol-4-yl)methyl
CF2CF3


467
CH2-(2-thiazolyl)
CF2CF3


468
CH2-(3-thiazolyl)
CF2CF3


469
CH2-(2-pyrrolyl)
CF2CF3


470
CH2-(3-pyrrolyl)
CF2CF3


471
CH2-(5-methylpyrazolyl-1-yl)
CF2CF3

















TABLE B








R


 

















R4
R5





472
CH2-(1-pyrazolyl)
CF2CF3


473
CH2-(2-pyrazolyl)
CF2CF3


474
CH2-(3-pyrazolyl)
CF2CF3


475
CH2-(4-pyrazolyl)
CF2CF3


476
CH2-(5-pyrazolyl)
CF2CF3


477
CH2-(2-oxazolyl)
CF2CF3


478
CH2-(3-oxazolyl)
CF2CF3


479
CH2-(3-isoxazolyl)
CF2CF3


480
CH2-(4-isoxazolyl)
CF2CF3


481
CH2-(5-isoxazolyl)
CF2CF3


482
CH2CH2OCH3
CF2CF3


483
CH2CH2OCH2CH3
CF2CF3


484
CH2CH2CH2OCH3
CF2CF3


485
CH2CH2CH2OCH2CH3
CF2CF3


486
CH2CH2SCH3
CF2CF3


487
CH2CH2SCH2CH3
CF2CF3


488
CH2CH2CH2SCH3
CF2CF3


489
CH2CH2CH2SCH2CH3
CF2CF3


490
Me
CH2CF3


491
Et
CH2Cl


492
n-Pr
CHCl2


493
i-Pr
CCl3


494
t-Bu
CHClBr


495
n-Bu
CHBr2


496
n-Pentyl
CH═CH2


497
n-Hexyl
CH2CH═CH2


498
cyclopropyl
CH2C≡CH












R


 

















R6
R7





499
H
CF3


500
Me
CF3


501
Et
CF3


502
n-Pr
CF3


503
i-Pr
CF3


504
t-Bu
CF3


505
cyclopropyl
CF3


506
CH═CH2
CF3


507
CH2CH═CH2
CF3


508
CH2C≡CH
CF3


509
Ph
CF3


510
CH2Ph
CF3


511
COMe
CF3


512
COEt
CF3


513
CO-n-Pr
CF3


514
CO-i-Pr
CF3


515
CO-cyclopropyl
CF3


516
COCH═CH2
CF3


517
COCH2CH═CH2
CF3


518
COCH2C≡CH
CF3


519
COPh
CF3


520
CO-(2-pyridyl)
CF3

















TABLE B








R


 

















R6
R7





521
CO-(3-pyridyl)
CF3


522
CO-(4-pyridyl)
CF3


523
COOMe
CF3


524
COOEt
CF3


525
COO-i-Pr
CF3


526
COO-t-Bu
CF3


527
COOPh
CF3


528
SO2Me
CF3


529
SO2Et
CF3


530
SO2Ph
CF3


531
SO2-(4-methylphenyl)
CF3


532
NHMe
CF3


533
NHEt
CF3


534
NH-n-Pr
CF3


535
NHCH2CH2Cl
CF3


536
NHCH2Ph
CF3


537
N(Me)2
CF3


538
Me
CHF2


539
Et
CHF2


540
n-Pr
CHF2


541
i-Pr
CHF2


542
t-Bu
CHF2


543
cyclopropyl
CHF2


544
CH═CH2
CHF2


545
CH2CH═CH2
CHF2


546
CH2C≡CH
CHF2


547
Ph
CHF2


548
CH2Ph
CHF2


549
COMe
CHF2


550
COEt
CHF2


551
CO-n-Pr
CHF2


552
CO-i-Pr
CHF2


553
CO-cyclopropyl
CHF2


554
COCH═CH2
CHF2


555
COCH2CH═CH2
CHF2


556
COCH2C≡CH
CHF2


557
COPh
CHF2


558
CO-(2-pyridyl)
CHF2


559
CO-(3-pyridyl)
CHF2


560
CO-(4-pyridyl)
CHF2


561
COOMe
CHF2


562
COOEt
CHF2


563
COO-i-Pr
CHF2


564
COO-t-Bu
CHF2


565
COOPh
CHF2


566
SO2Me
CHF2


567
SO2Et
CHF2


568
SO2Ph
CHF2


569
SO2-(4-methylphenyl)
CHF2


570
Me
CF2Cl


571
Et
CF2Cl


572
n-Pr
CF2Cl


573
i-Pr
CF2Cl


574
t-Bu
CF2Cl

















TABLE B








R


 

















R6
R7





575
cyclopropyl
CF2Cl


576
CH═CH2
CF2Cl


577
CH2CH═CH2
CF2Cl


578
CH2C≡CH
CF2Cl


579
Ph
CF2Cl


580
CH2Ph
CF2Cl


581
COMe
CF2Cl


582
COEt
CF2Cl


583
CO-n-Pr
CF2Cl


584
CO-i-Pr
CF2Cl


585
CO-cyclopropyl
CF2Cl


586
COCH═CH2
CF2Cl


587
COCH2CH═CH2
CF2Cl


588
COCH2C≡CH
CF2Cl


589
COPh
CF2Cl


590
CO-(2-pyridyl)
CF2Cl


591
CO-(3-pyridyl)
CF2Cl


592
CO-(4-pyridyl)
CF2Cl


593
COOMe
CF2Cl


594
COOEt
CF2Cl


595
COO-i-Pr
CF2Cl


596
COO-t-Bu
CF2Cl


597
COOPh
CF2Cl


598
SO2Me
CF2Cl


599
SO2Et
CF2Cl


600
SO2Ph
CF2Cl


601
SO2-(4-methylphenyl)
CF2Cl


602
Me
CF2CF3


603
Et
CF2CF3


604
n-Pr
CF2CF3


605
i-Pr
CF2CF3


606
t-Bu
CF2CF3


607
cyclopropyl
CF2CF3


608
CH═CH2
CF2CF3


609
CH2CH═CH2
CF2CF3


610
CH2C≡CH
CF2CF3


611
Ph
CF2CF3


612
CH2Ph
CF2CF3


613
COMe
CF2CF3


614
COEt
CF2CF3


615
CO-n-Pr
CF2CF3


616
CO-i-Pr
CF2CF3


617
CO-cyclopropyl
CF2CF3


618
COCH═CH2
CF2CF3


619
COCH2CH═CH2
CF2CF3


620
COCH2C≡CH
CF2CF3


621
COPh
CF2CF3


622
CO-(2-pyridyl)
CF2CF3


623
CO-(3-pyridyl)
CF2CF3


624
CO-(4-pyridyl)
CF2CF3


625
COOMe
CF2CF3


626
COOEt
CF2CF3


627
COO-i-Pr
CF2CF3

















TABLE B








R


 

















R6
R7





628
COO-t-Bu
CF2CF3


629
COOPh
CF2CF3


630
SO2Me
CF2CF3


631
SO2Et
CF2CF3


632
SO2Ph
CF2CF3


633
SO2-(4-methylphenyl)
CF2CF3


634
Me
CH2CF3


635
Et
CH2Cl


636
n-Pr
CHCl2


637
i-Pr
CCl3


638
t-Bu
CHClBr


639
cyclopropyl
CHBr2


640
CH═CH2
CH═CH2


641
CH2CH═CH2
CH2CH═CH2


642
CH2C≡CH
CH2C≡CH

















TABLE B






R














 



R1





643
C6F5


644
CH2OCH2C6H5












 



R2





645
CH2C6H5


646
isopropyl


697
CH2CH2CH═CH2












 



R3





648
C6F5


649
CH2OCH2C6H5

















TABLE B








R


 

















R4
R5





650
Ethyl
CH2CF3


651
n-Propyl
CH2CF3


652
iso-Propyl
CH2CF3


653
t-Butyl
CH2CF3


654
n-Butyl
CH2CF3


655
cyclopropyl
CH2CF3


656
cyclopentyl
CH2CF3


657
cyclohexyl
CH2CF3


658
n-hexa decyl
CF3


659
n-tridecyl
CF3


660
CH(CH3)CH2CH3
CF3


661
CH(CH3)CH2CH2CH3
CF3


662
CH(CH3)-isopropyl
CF3


663
1-phenylethyl
CF3


664
1,2,3,4-tetrahydronaphthalen-1-yl
CF3


665
1-(naphthalen-1-yl)ethyl
CF3


666
1-(naphthalen-1-yl)propyl
CF3


667
1-(furan-2-yl)ethyl
CF3


668
3.3-dimethylbutan-2-yl
CF3


669
1-(thiophen-2-yl)ethyl
CF3


670
CH2CH2F
CF3


671
n-Octyl
CF3


672
n-Octyl
CHF2


673
n-Octyl
CF2Cl


674
n-Octyl
CF2CF3


675
n-Octyl
CF2CF3


676
CH(C6H5)2
CF3


677
CH(C6H5)2
CHF2


678
CH(C6H5)2
CF2Cl


679
CH(C6H5)2
CF2CF3


680
CH(C6H5)2
CH2CF3


681
CH(CH2CH3)2
CF3


682
CH(CH2CH3)2
CHF2


683
CH(CH2CH3)2
CF2Cl


684
CH(CH2CH3)2
CF2CF3


685
CH(CH2CH3)2
CH2CF3


686
CH(CH2CH2CH3)2
CF3


687
CH(CH2CH2CH3)2
CHF2


688
CH(CH2CH2CH3)2
CF2Cl


689
CH(CH2CH2CH3)2
CF2CF3


690
CH(CH2CH2CH3)2
CF2CF3

















TABLE B








R


 


















Y1
Y2
Ry





691
O
O
Methyl


692
O
O
Ethyl


693
O
O
Propyl


694
O
O
isopropyl


695
S
O
Methyl


696
S
O
Ethyl


697
S
O
Propyl


698
S
O
isopropyl


699
S
S
Methyl


700
S
S
Ethyl


701
S
S
Propyl


702
S
S
isopropyl


























n
Rz





703
1
CF3


704
1
CF2CF3


705
1
CH2CF3


706
1
Me


707
2
CF3


708
2
CF2CF3


709
2
CH2CF3


710
2
Me









Examples of preferred compounds of Formula (I) include compounds shown in the following Tables.











TABLE 36





Compound






No
Ar
A
Y
R







266-2  
6-Chloro-3-
A-38
H
COCF3



pyridyl


444-2  
2-chloro-5-
A-38
H
COCF3



thiazolyl


190-2  
6-Chloro-3-
A-13
H
COCF3



pyridyl


201-2  
6-Chloro-3-
A-14
H
COCF3



pyridyl


223-2  
6-Chloro-3-
A-16
H
COCF3



pyridyl


146-2  
6-Chloro-3-
A-1
3-
COCF3



pyridyl

OH


224-2  
2-chloro-5-
A-16
H
COCF3



thiazolyl


102-2  
6-Chloro-3-
A-1
3-
COCF3



pyridyl

CN


212-2  
6-Chloro-3-
A-15
H
COCF3



pyridyl


1-20
6-Chloro-3-
A-1
H
CSCF3



pyridyl


12-2 
2-Chloro-4-
A-1
H
COCF3



pyridyl


213-2  
2-chloro-5-
A-15
H
COCF3



thiazolyl


1-17
6-Chloro-3-
A-1
H
COOCH2CF3



pyridyl


1-18
6-Chloro-3-
A-1
H
COOCH(Me)CF3



pyridyl


1-19
6-Chloro-3-
A-1
H
COOCH(CF3)2



pyridyl


7-2 
5-Chloro-
A-1
H
COCF3



pyrazin-2-yl


1-13
6-Chloro-3-
A-1
H
COCH2CF3



pyridyl


168-2  
6-Chloro-3-
A-1
5-
COCF3



pyridyl

OH


1-21
6-Chloro-3-
A-1
H
CSCHF2



pyridyl


3-20
6-Fluoro-3-
A-1
H
CSCF3



pyridyl


4-20
6-Bromo-3-
A-1
H
CSCF3



pyridyl


3-3 
6-Fluoro-3-
A-1
H
COCHF2



pyridyl


4-3 
6-Bromo-3-
A-1
H
COCHF2



pyridyl


5-5 
6-Chloro-5-
A-1
H
COCF2CF3



fluoro-3-pyridyl


6-5 
2-Chloro-5-
A-1
H
COCF2CF3



pyrimidinyl


1-22
6-Chloro-3-
A-1
H
CSCF2Cl



pyridyl


1-23
6-Chloro-3-
A-1
H
CSCF2CF3



pyridyl


5-20
6-Chloro-5-
A-1
H
CSCF3



fluoro-3-pyridyl


5-3 
6-Chloro-5-
A-1
H
COCHF2



fluoro-3-pyridyl


6-3 
2-Chloro-5-
A-1
H
COCHF2



pyrimidinyl


8-2 
6-Chloro-
A-1
H
COCF3



pyridazin-3-yl


5-4 
6-Chloro-5-
A-1
H
COCF2Cl



fluoro-3-pyridyl


4-4 
6-Bromo-3-
A-1
H
COCF2Cl



pyridyl


6-4 
2-Chloro-5-
A-1
H
COCF2Cl



pyrimidinyl


4-5 
6-Bromo-3-
A-1
H
COCF2CF3



pyridyl


2-20
2-chloro-5-
A-1
H
CSCF3



thiazolyl


10-20 
6-tri-
A-1
H
CSCF3



fluoromethyl-



3-pyridyl


3-4 
6-Fluoro-3-
A-1
H
COCF2Cl



pyridyl


3-5 
6-Fluoro-3-
A-1
H
COCF2CF3



pyridyl


11-20 
3-THF
A-1
H
CSCF3


1-14
6-Chloro-3-
A-1
H
COCH═CH2



pyridyl


1-37
6-Chloro-3-
A-1
H
CSEt



pyridyl


1-39
6-Chloro-3-
A-1
H
CS—i-Pr



pyridyl


1-40
6-Chloro-3-
A-1
H
CS-cyclopropyl



pyridyl


1-15
6-Chloro-3-
A-1
H
COCH2CΞCH



pyridyl


1-35
6-Chloro-3-
A-1
H
CSCH2CH2Ph



pyridyl


 1-501
6-Chloro-3-
A-1
H
C(═NOEt)CF3



pyridyl


 1-499
6-Chloro-3-
A-1
H
C(═NOH)CF3



pyridyl


 1-510
6-Chloro-3-
A-1
H
C(═NOCH2Ph)CF3



pyridyl


 1-511
6-Chloro-3-
A-1
H
C(═NOCOMe)CF3



pyridyl


 1-519
6-Chloro-3-
A-1
H
C(═NOCOPh)CF3



pyridyl


 1-523
6-Chloro-3-
A-1
H
C(═NOCOOMe)CF3



pyridyl




















TABLE 37





Compound






No
Ar
A
Y
R







1-528
6-Chloro-3-
A-1
H
C(═NOSO2Me)CF3



pyridyl


1-531
6-Chloro-3-
A-1
H
C(═NOSO2-(4-



pyridyl


Methylphenyl))CF3


1-507
6-Chloro-3-
A-1
H
C(═NOCH2CH═CH2)CF3



pyridyl


1-516
6-Chloro-3-
A-1
H
C(═NOCOCH═CH2)CF3



pyridyl


1-518
6-Chloro-3-
A-1
H
C(═NOCOCH2C≡CH)CF3



pyridyl


1-527
6-Chloro-3-
A-1
H
C(═NOCOOPh)CF3



pyridyl


1-521
6-Chloro-3-
A-1
H
C(═NOCO-3-pyr)CF3



pyridyl


1-43 
6-Chloro-3-
A-1
H
C(═NEt)CF3



pyridyl


1-536
6-Chloro-3-
A-1
H
C(═NOCONHCH2Ph)CF3



pyridyl


1-42 
6-Chloro-3-
A-1
H
C(═NMe)CF3



pyridyl


1-500
6-Chloro-3-
A-1
H
C(═NOMe)CF3



pyridyl


1-504
6-Chloro-3-
A-1
H
C(═NOtBu)CF3



pyridyl


1-534
6-Chloro-3-
A-1
H
C(═NOCONHnPr)CF3



pyridyl


1-535
6-Chloro-3-
A-1
H
C(═NOCONHCH2CH2Cl)CF3



pyridyl


1-72 
6-Chloro-3-
A-1
H
C(═NCH2Ph)CF3



pyridyl


1-150
6-Chloro-3-
A-1
H
C(═NCH2CH2SMe)CF3



pyridyl


1-67 
6-Chloro-3-
A-1
H
C(═NCH2CH2OH)



pyridyl


1-515
6-Chloro-3-
A-1
H
C(═NOCO-



pyridyl


cyclopropyl)CF3


1-56 
6-Chloro-3-
A-1
H
C(═NCH2C Ξ CH)CF3



pyridyl


1-512
6-Chloro-3-
A-1
H
C(═NOCOCH2CH3)CF3



pyridyl


1-514
6-Chloro-3-
A-1
H
C(═NOCOiPr)CF3



pyridyl


1-50 
6-Chloro-3-
A-1
H
C(═N-cyclopropyl)CF3



pyridyl


1-114
6-Chloro-3-
A-1
H
C(═NCH2CH2OPh)CF3



pyridyl


1-44 
6-Chloro-3-
A-1
H
C(═N—n-Pr)CF3



pyridyl


1-118
6-Chloro-3-
A-1
H
C(═NCH2-(2-



pyridyl


pyridyl))CF3


1-119
6-Chloro-3-
A-1
H
C(═NCH2-(3-



pyridyl


pyridyl))CF3


1-47 
6-Chloro-3-
A-1
H
C(═N—n-Bu)CF3



pyridyl


1-55 
6-Chloro-3-
A-1
H
C(═N—CH2CH═CH2)CF3



pyridyl


1-122
6-Chloro-3-
A-1
H
C(═NCH2-(2-



pyridyl


thienyl))CF3


1-45 
6-Chloro-3-
A-1
H
C(═N—i-Pr)CF3



pyridyl


1-124
6-Chloro-3-
A-1
H
C(═NCH2-(2-



pyridyl


furanyl))CF3


1-126
6-Chloro-3-
A-1
H
C(═NCH2-(2-



pyridyl


tetrahydrofuranyl))CF3


1-64 
6-Chloro-3-
A-1
H
C(═NCH2CN)CF3



pyridyl


1-146
6-Chloro-3-
A-1
H
C(═NCH2CH2OCH3)CF3



pyridyl


1-52 
6-Chloro-3-
A-1
H
C(═N-cyclopentyl)CF3



pyridyl


1-121
6-Chloro-3-
A-1
H
C(═NCH2-(4-



pyridyl


pyridyl))CF3


1-53 
6-Chloro-3-
A-1
H
C(═N-cyclohexyl)CF3



pyridyl


1-76 
6-Chloro-3-
A-1
H
C(═NCH2CH2Ph)CF3



pyridyl


267-2  
6-Chloro-3-
A-39
H
COCF3



pyridyl


253-2  
6-Chloro-3-
A-25
H
COCF3



pyridyl


251-2  
6-Chloro-3-
A-23
H
COCF3



pyridyl


13-2  
3-
A-1
H
COCF3



Cyanophenyl


1-1 
6-Chloro-3-
A-1
H
CHO



pyridyl


1-41 
6-Chloro-3-
A-1
H
C(═NH)CF3



pyridyl




















TABLE 38





Compound






No.
Ar
A
Y
R







1-647
6-Chloro-3-
A-1
H
COOCH2CH2CH═CH2



pyridyl


1-670
6-Chloro-3-
A-1
H
C(═NCH2CH2F)CF3



pyridyl


157-2  
6-Chloro-3-
A-1
4-
COCF3



pyridyl

OH


1-10 
6-Chloro-3-
A-1
H
CO(2,2-



pyridyl


difluonocyclopropyl)


580-2  
6-chloro-3-
A-1
H
COCF3



pyridyl-N-



oxid


1-671
6-Chloro-3-
A-1
H
C(═N(CH2)7CH3)CF3



pyridyl


1-658
6-Chloro-3-
A-1
H
C(═N(CH2)15CH3)CF3



pyridyl


1-659
6-Chloro-3-
A-1
H
C(═N(CH2)11CH3)CF3



pyridyl


1-660
6-Chloro-3-
A-1
H
C(═NCH(CH3)CH2CH3)CF3



pyridyl


1-681
6-Chloro-3-
A-1
H
C(═NCH(CH2CH3)2)CF3



pyridyl


1-686
6-Chloro-3-
A-1
H
C(═NCH(CH2CH2CH3)2)CF3



pyridyl


1-661
6-Chloro-3-
A-1
H
C(═NCH(CH3)CH2CH2CH3)CF3



pyridyl


1-662
6-Chloro-3-
A-1
H
C(═NCH(iso-



pyridyl


propyl)CH3)CF3


1-663
6-Chloro-3-
A-1
H
C(═N(1-phenylethyl))CF3



pyridyl


1-664
6-Chloro-3-
A-1
H
C(═N(1,2,3,4-



pyridyl


tetrahydronaphthalen-1-






yl)CF3


1-665
6-Chloro-3-
A-1
H
C(═N(1-(naphthalen-1-



pyridyl


yl)ethyl))CF3


1-666
6-Chloro-3-
A-1
H
C(═N(1-(naphthalen-1-



pyridyl


yl)propyl))CF3


1-667
6-Chloro-3-
A-1
H
C(═N(1-(furan-2-



pyridyl


yl)ethyl))CF3


1-676
6-Chloro-3-
A-1
H
C(═NCH(C6H5)2)CF3



pyridyl


1-668
6-Chloro-3-
A-1
H
C(═N(3,3-dimethylbutan-



pyridyl


2-yl))CF3


47-2  
6-Chloro-3-
A-1
6-
COCF3



pyridyl

F


91-2  
6-Chloro-3-
A-1
6-
COCF3



pyridyl

Cl


478-2  
6-Chloro-3-
A-1
6-
COCF3



pyridyl

CH3


479-2  
2-Chloro-5-
A-1
6-
COCF3



thiazolyl

CH3


1-51 
6-Chloro-3-
A-1
H
C(═N-cyclobutyl)CF3



pyridyl


566-2  
6-Chloro-3-
A-1
6-
COCF3



pyridyl

CH3O


488-2  
3-
A-1
6-
COCF3



tetrahydrofu-

CH3



ranyl


511-2  
6-Chloro-3-
A-1
5-
COCF3



pyridyl

NO2


1-669
6-Chloro-3-
A-1
H
C(═N(1-(thiophen-



pyridyl


2-yl)ethyl))CF3


179-2  
6-Chloro-3-
A-1
6-
COCF3 (also represents



pyridyl

OH
a tautomer)


555-2  
6-Chloro-3-
A-1
5-
COCF3



pyridyl

OCH3


577-2  
2,6-dichrolo-
A-1
H
COCF3



3-pyridyl


544-2  
6-Chloro-3-
A-1
4-
COCF3



pyridyl

OCH3


168-2  
6-Chloro-3-
A-1
5-
COCF3



pyridyl

OH


1-644
6-Chloro-3-
A-1
H
COCH2OCH2C6H5



pyridyl


578-644 
3-pyridyl
A-1
H
COCH2OCH2C6H5


1-703
6-Chloro-3-
A-1
H
SOCF3



pyridyl


1-707
6-Chloro-3-
A-1
H
SO2CF3



pyridyl


1-706
6-Chloro-3-
A-1
H
SOCH3



pyridyl


1-692
6-Chloro-3-
A-1
H
P(═O)(OEt)2



pyridyl


1-700
6-Chloro-3-
A-1
H
P(═S)(SEt)2



pyridyl


1-701
6-Chloro-3-
A-1
H
P(═S)(S-n-propyl)2



pyridyl


1-702
6-Chloro-3-
A-1
H
P(═S)(S-isopropyl)2



pyridyl


1-646
6-Chloro-3-
A-1
H
COO-iso-Pr



pyridyl


1-645
6-Chloro-3-
A-1
H
COOCH2C6H5



pyridyl


1-643
6-Chloro-3-
A-1
H
COC6F5



pyridyl


2-643
2-Chloro-5-
A-1
H
COC6F5



thiazolyl
















TABLE 39













 












Compound






No.
Ar
R1a
Y







P212
6-chloro-3-
CF3
H




pyridyl





P213
2-chloro-5-
CF3
H




thiazolyl





P214
6-chloro-3-
OCH3
H




pyridyl





P215
6-chloro-3-
CF3
5-Cl




pyridyl





P216
6-chloro-3-
CF3
5-F




pyridyl





P217
6-chloro-3-
CF3
4-Cl




pyridyl





P218
2-chloro-5-
CF3
5-Cl




thiazolyl





P219
2-chloro-5-
CF3
5-F




thiazolyl





P220
2-chloro-5-
CF3
4-Cl




thiazolyl





P221
6-chloro-3-
CF3
3-Me




pyridyl





P222
6-chloro-3-
CF3
4-Me




pyridyl





P223
6-chloro-3-
CF3
5-Me




pyridyl





P224
phenyl
CF3
H



P225
4-chloro-
CF3
H




phenyl





P226
3-pyridyl
CF3
H



P227
6-chloro-
CF3
H




5-fluoro-






3-pyridyl





P228
6-trifluoro-
CF3
H




methyl-






3-pyridyl





P229
6-fluoro-
CF3
H




3-pyridyl





P230
5,6-dichloro-
CF3
H




3-pyridyl





P231
6-bromo-
CF3
H




3-pyridyl





P232
6-chloro-3-
CF3
4-F




pyridyl





P233
6-chloro-3-
CF3
3-F




pyridyl





P234
6-chloro-3-
CHCl2
H




pyridyl





P235
6-chloro-3-
CCl3
H




pyridyl





P236
6-chloro-3-
CH2Cl
H




pyridyl





P238
6-chloro-3-
CHF2
H




pyridyl





P239
6-chloro-3-
CF2Cl
H




pyridyl





P240
6-chloro-3-
CHClBr
H




pyridyl





P241
6-chloro-3-
CHBr2
H




pyridyl





P242
6-chloro-3-
CF2CF3
H




pyridyl





P243
2-chloro-5-
CF3
H




pyrimidinyl





P244
6-chloro-3-
CH2Br
H




pyridyl










Examples of more preferred compounds include

    N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P212) and
    N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (Compound 1-20), N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide (Compound 1-45).


In addition, in the present invention, an acid addition salt of a novel iminopyridine derivative represented by Formula (I) (preferably, an agriculturally and zootechnically acceptable acid addition salt) may also be used, and examples thereof include an acid addition salt such as hydrochloride, nitrate, sulfate, phosphate, or acetate and the like.
The novel iminopyridine derivative represented by Formula (I) itself shows excellent pest control effects against pest insects, and is mixed and used with other pest control agents, thereby showing excellent pest control effects compared to when a single agent is used. Therefore, the present invention provides a pest control composition prepared by containing at least one of novel iminopyridine derivatives represented by Formula (I) and at least one of other pest control agents. Furthermore, the present invention provides an excellent pest control composition prepared by containing at least one of novel iminopyridine derivatives represented by Formula (I) and at least one of other insecticides and/or fungicides.
Examples of a pest control composition provided by the present invention include a pest control agent for agricultural and horticultural, a control agent for animal parasitic pests, an agent for controlling hygiene pests, an agent for controlling nuisance pests, an agent for controlling stored grain and stored product pests, an agent for controlling house pests and the like, preferred examples thereof include a pest control agent for agricultural and horticultural and a control agent for animal parasitic pests.
Examples of the insect species against which a pest control composition containing a novel iminopyridine derivative represented by Formula (I) or at least one of acid addition salts thereof, and at least one of other pest control agents shows pest control effects include lepidopteran pests (for example, Spodoptera litura, cabbage armyworm, Mythimna separata, cabbageworm, cabbage moth, Spodoptera exigua, rice stem borer, grass leaf roller, tortricid, codling moth, leafminer moth, tussock moth, Agrotis spp), Helicoverpa spp, Heliothis spp and the like), hemipteran pests (for example, aphids (Aphididae, Adelgidae, Phylloxeridae) such as Myzus persicae, Aphis gossypii, Aphis fabae, corn leaf aphid, pea aphid, Aulacorthum solani, Aphis craccivora, Macrosiphum euphorbiae, Macrosiphum avenae, Methopolophium dirhodum, Rhopalosiphum padi, greenbug, Brevicoryne brassicae, Lipaphis erysimi, Aphis citricola, Rosy apple aphid, apple blight, Toxoptera aurantii and Toxoptera citricidus, leafhoppers such as Nephotettix cincticeps and Empoasca vitis, planthoppers such as Laodelphax striatellus, Nilaparvata lugens and Sogatella furcifera, Pentatomorpha such as Eysarcoris ventralis, Nezara viridula and Trigonotylus coelestialium, whiteflies (Aleyrodidae) such as silverleaf whitefly, Bemisia tabaci and greenhouse whitefly, and scale insects (Diaspididae, Margarodidae, Ortheziidae, Aclerdiae, Dactylopiidae, Kerridae, Pseudoccccidae, Coccidae, Eriococcidae, Asterolecaniidae, Beesonidae, Lecanodiaspididae, Cerococcidae and the like) such as Pseudococcus comstocki, Planococcus citri, Pseudaulacaspis pentagona and Aonidiella aurantii), coleopteran pests (for example, Lissorhoptrus oryzophilus, Callosobruchus chinensis, Tenebrio molitor, Diabrotica virgifera virgifera, Diabrotica undecimpunctata howardi, Anomala cuprea, Anomala rufocuprea, Phyllotreta striolata, Aulacophora femoralis, Leptinotarsa decemlineata, Oulema oryzae, Bostrichidae, Cerambycidae and the like), Acarina (for example, Tetranychus urticae, Tetranychus kanzawai, Panonychus citri and the like), hymenopteran pests (for example, Tenthredinidae), orthopteran pests (for example, Acridioidea), dipteran pests (for example, Agromyzidae), thysanopteran pests (for example, Thrips palmi, Frankliniella occidentalis and the like), phytoparasitic nematode (for example, Meloidogyne, Pratylenchus, Aphelenchoides besseyi, Bursaphelenchus xylophilus and the like), and the like, examples of zooparasites include Ixodidae (for example, Amblyomma americanum, Amblyomma maculatum, Boophilus microplus, Dermacentor andersoni, Dermacentor occidentalis, Dermacentor variabilis, Haemaphysalis campanulata, Haemaphysalis flava, Haemaphysalis longicornis, Haemaphysalis megaspinosa Saito, Ixodes nipponensis, Ixodes ovatus, Ixodes pacifcus, Ixodes persulcatus, Ixodes ricinus, Ixodes scapularis, Ornithodoros moubata pacifcus and Rhipicephalus sanguineus), Cheyletidae (for example, Cheyletiella blakei and Cheyletiella yasguri), Demodex (for example, Demodex canis and Demodex cati), Psoroptidae (for example, Psoroptes communis), Sarcoptidae (for example, Chorioptes bovis and Otodectes cynotis), Dermanyssidae (for example, Ornithonyssus sylviarum), Dermanyssus gallinae, Pterolichus (for example, Megninia cubitalis and Pterolichus obtusus), Trombiculidae (for example, Helenicula miyagawai and Leptotrombidium akamushi), Shiphonaptera (for example, Ctenocephalides felis, Pulex irritans, Xenopsylla cheopis and Xenopsylla), Mallophaga (for example, Trichodectes canis and Menopon gallinae), Anoplura (for example, Haematopinus suis, Linognathus setosus, Pediculus humanus humanus, Pediculus humanus, Pthirus pubis and Cimex lectularius), Diptera (for example, Musca domestica, Hypoderma bovis, Stomoxys calcitrans and Gasterophilus), Psychodidae (for example, Phlebotomus), Glossina morsitans, Tabanidae, Ormosia tokionis (for example, Aedes albopictus and Aedes aegypti), Culicidae (for example, Culex pipiens pallens), Anophelini, Ceratopogonidae and the like), Simuliidae, Ceratopogonidae, Reduviidae, Monomorium pharaonis, Nematoda (for example, Strongyloides, Ancylostomatoidea, Strongyloidea (for example, Haemonchus contortus and Nippostrongylus braziliensis), Trichostrongyloidea, Metastrongyloidea (for example, Metastrongylus elongatus, Angiostrongylus cantonensis and Aelurostrongylus abstrutus), Oxyuroidea, Haterakoidea (for example, Ascaridia galli), Ascaridoidea (for example, Anisakis simplex, Ascaris suum, Parascaris equorum, Toxocara canis and Toxocara cati), Spiruroidea (for example, Subuluroidea, Gnathostoma spinigerum, Physaloptea praeputialis, Ascarops strongylina, Draschia megastoma and Ascaria hamulosa, Dracunculus medinensis), Filarioidea (for example, Dirofilaria immitis, lymphatic filarial, Onchocerca volvulus and Loa loa), Dioctophymatoidea, Trichinella (for example, Trichuris vulpis and Trichinella spiralis), Trematoda (for example, Schistosoma japonicum and Fasciola hepatica), Acanthocephala, Taenia (for example, Pseudophyllidea (for example, Spirometra erinaceieuropaei) and Cyclophyllidea (for example, Dipylidium caninum)), Protozoa, and the like, and examples of hygiene pests include Periplaneta (for example, Blattella germanica), Acaridae (for example, Tyrophagus putrescentiae), and Isoptera (for example, Coptotermes formosanus). Among them, preferred examples of an insect species, to which the pest control agent of the present invention is applied, include lepidopteran pests, hemipteran pests, thysanopteran pests, dipteran pests, coleopteran pests, zooparasitic Shiphonaptera or Acari, Dirofilaria immitis, Periplaneta and Isoptera (for example, at least one insect species selected from the group consisting of cabbage moth, Spodoptera litura, Aphis gossypii, Myzus persicae, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Nephotettix cincticeps, Frankliniella occidentalis, Aulacophora femoralis, Oulema oryzae, Lissorhoptrus oryzophilus, Trigonotylus coelestialium, Musca domestica, Haemaphysalis longicornis, Dirofilaria immitis, Blattella germanica and Coptotermes formosanus), and particularly preferred examples thereof include cabbage moth, Aphis gossypii, Myzus persicae, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Nephotettix cincticeps, Aulacophora femoralis, Oulema oryzae, Lissorhoptrus oryzophilus, Trigonotylus coelestialium, Musca domestica and Haemaphysalis longicornis. 
In the present specification, examples of other pest control agents which may be mixed with the novel iminopyridine derivative represented by Formula (I) include an insecticide, a fungicide, a miticide, a herbicide, a plant growth regulator and a control agent for animal parasites, and examples of a specific chemical include those described in The Pesticide Manual (13th edition and published by the British Crop Protection Council) and the SHIBUYA INDEX (15th edition, 2010 and published by SHIBUYA INDEX RESEARCH GROUP).
Examples of other pest control agents which may be mixed with the novel iminopyridine derivative represented by Formula (I) preferably include an insecticide, a fungicide, a herbicide and a control agent for animal parasitic pests, and also those prepared by mixing a fungicide with an insecticide.
Preferred examples of other pest control agents which may be mixed with the novel iminopyridine derivative represented by Formula (I) include an organic phosphoric ester compound, a carbamate-based compound, a nereistoxin derivative, an organochlorine compound, a pyrethroid-based compound, a benzoyl urea-based compound, a juvenile hormone-like compound, a molting hormone-like compound, a neonicotinoid-based compound, a sodium channel blocker for nerve cells, an insecticidalmacrocyclic lactone, a γ-aminobutyric acid (GABA) antagonist, a ryanodine receptor agonistic compound, insecticidal ureas, a BT agent, an entomopathogenic viral agent and the like, as an insecticide, and more preferred examples thereof include an organic phosphoric ester compound such as acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenofos, pyraclofos, chlorpyrifos-methyl, diazinon, trichlorfon, tetrachlorvinphos, bromofenofos and cythioate, a carbamate-based compound such as methomyl, thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicarb, carbofuran and benfuracarb, a nereistoxin derivative such as cartap and thiocyclam, an organochlorine compound such as dicofol and tetradifon, a pyrethroid-based compound such as allethrin, d•d-T allethrin, dl•d-T80 allethrin, pyrethrins, phenothrin, flumethrin, cyfluthrin, d•d-T80 prarethrin, phthalthrin, transfluthrin, resmethrin, cyphenothrin, pyrethrum extract, synepirin222, synepirin500, permethrin, tefluthrin, cypermethrin, deltamethrin, cyhalothrin, fenvalerate, fluvalinate, ethofenprox and silafluofen, a benzoyl urea-based compound such as diflubenzuron, teflubenzuron, flufenoxuron, chlorfluazuron and lufenuron, a juvenile hormone-like compound such as methoprene and a molting hormone-like compound such as chromafenozide. In addition, examples of other compounds include buprofezin, hexythiazox, amitraz, chlordimeform, pyridaben, fenpyroxymate, Pyrimidifen, tebufenpyrad, tolfenpyrad, acequinocyl, cyflumetofen, flubendizmide, ethiprole, fipronil, etoxazole, imidacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, thiacloprid, dinotefuran, pymetrozine, bifenazate, spirodiclofen, spiromesifen, spirotetramat, flonicamid, chlorfenapyr, pyriproxyfen, indoxacarb, pyridalyl, spinosad, spinetoram, avermectin, milbemycin, pyflubumide, cyenopyrafen, pyrifluquinazon, chlorantraniliprole, cyantraniliprole, lepimectin, metaflumizone, pyrafluprole, pyriprole, hydramethylnon, triazamate, sulfoxaflor, flupyradifurone, flometoquin, ivermectin, selamectin, moxidectin, doramectin, eprinomectin, milbemycin oxime, deet, metoxadiazon, cyromazine, triflumuron, star anise oil, triclabendazole, flubendazole, fenbendazole, antimony sodium gluconate, levamisole hydrochloride, bithionol, dichlorofen, phenothiazine, piperazine carbon bisulfide, piperazine phosphate, piperazine adipate, piperazine citrate, melarsomine dihydrochloride, metyridine, santonin, pyrantel pamoate, pyrantel, praziquantel, febantel, emodepside, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, an organic metal-based compound, a dinitro-based compound, an organic sulfur compound, a urea-based compound, a triazine-based compound, a hydrazine-based compound, and a compound represented by the following Formula (II) or agriculturally and zootechnically acceptable acid addition salts thereof. Examples of those acid addition salts include hydrochloride, nitrate, sulfate, phosphate, or acetate and the like.




[in the formula (II), Het1 represents a 3-pyridyl group,
R1 represents a hydroxyl group,
R2 and R3 represent a cyclopropylcarbonyloxy group, and
R4 represents a hydroxyl group]
More preferred examples of other insecticides which may be mixed with the novel iminopyridine derivative represented by Formula (I) include acetamiprid, imidacloprid, nitenpyram, clothianidin, acetamiprid, dinotefuran, thiacloprid, thiamethoxam, pymetrozine, spinosad, spinetram, fipronil, chloranthraniliprole, cyantraniliprole), cartap, thiocyclam, benfuracarb, buprofezin, ethofenprox, silafluofen, ethiprole, flonicamid, sulfoxaflor, flupyradifurone, flometoquin, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, afidopyropen, and the compound represented by Formula (II), or agriculturally and zootechnically acceptable acid addition salts thereof, and particularly preferred examples thereof include permethrin, acetamiprid, imidacloprid, clothianidin, dinotefuran, thiacloprid, thiamethoxam, pymetrozine, spinosad, spinetram, fipronil, chloranthraniliprole, cyantraniliprole, amitraz, ethofenprox, silafluofen, ethiprole, flonicamid, sulfoxaflor, flupyradifurone, flometoquin, ivermectin, moxidectin, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, and afidopyropen, or agriculturally and zootechnically acceptable acid addition salts thereof.
The novel iminopyridine derivative represented by Formula (I) may be used together or in combination with a microbial pesticide such as a BT agent and an entomopathogenic viral agent.
Examples of the fungicide which may be mixed with the novel iminopyridine derivative represented by Formula (I) include, for example, a strobilurin-based compound such as azoxystrobin, orysastrobin, kresoxym-methyl and trifloxystrobin, an anilinopyrimidine-based compound such as mepanipyrim, pyrimethanil and cyprodinil, an azole-based compound such as triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, prochloraz and simeconazole, a quinoxaline-based compound such as quinomethionate, a dithiocarbamate-based compound such as maneb, zineb, mancozeb, polycarbamate and propineb, a phenyl carbamate-based compound such as diethofencarb, an organochlorine compound such as chlorothalonil and quintozene, a benzimidazole-based compound such as benomyl, thiophanate-methyl and carbendazole, a phenyl amide-based compound such as metalaxyl, oxadixyl, ofurase, benalaxyl, furalaxyl and cyprofuram, a sulfenic acid-based compound such as dichlofluanid, a copper-based compound such as copper hydroxide and copper oxyquinoline (oxine-copper), an isoxazole-based compound such as hydroxyisoxazole, an organic phosphorus-based compound such as fosetyl-aluminium and tolclofos-methyl, an N-halogenothioalkyl-based compound such as captan, captafol and folpet, a dicarboximide-based compound such as procymidone, iprodione and vinchlozolin, a benzanilide-based compound such as thifluzamide, furametpyr, flutolanil and mepronil, a morpholine-based compound such as fenpropimorph and dimethomorph, an organic tin-based compound such as fenthin hydroxide and fenthin acetate, a cyanopyrrole-based compound such as fludioxonil and fenpiclonil, 9-membered cyclic dilactone compounds such as acibenzolar-S-methyl, isotianil, tiadinil, carpropamid, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, fthalide, fluazinam, cymoxanil, triforine, pyrifenox, probenazole, fenarimol, fenpropidin, pencycuron, cyazofamid, iprovalicarb, tebufloquin, benthiavalicarb-isopropyl, tolprocarb, validamycin, Kasugamycin, Streptomycin and UK-2As, a compound represented by the following Formula (III), which is described in JP-A No. 2009-078991, a compound represented by the following Formula (IV), which is described in Republication No. WO08/066148, and a compound represented by the following Formula (V), which is described in Republication No. WO09/028280, or agriculturally and zootechnically acceptable acid addition salts thereof.




[in the formula (III), R1 and R2 represent a hydrogen atom or a haloalkyl group having 1 to 6 carbon atoms and the like (however, at least one of R1 and R2 represents a haloalkyl group having 1 to 6 carbon atoms), R3 represents a hydrogen atom and the like, A represents OR4, SR5, NR6R7 or NR8NR9R10, R4 represents an alkyl group having 8 to 12 carbon atoms and the like, R5 represents an alkyl group having 1 to 12 carbon atoms and the like, R6 and R7 represent a hydrogen atom or an alkyl group having 8 to 12 carbon atoms, and R8, R9 and R10 represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms and the like]




[in the formula (IV), R1 and R2 represent a C1 to C6 alkyl group, an aryl group, a heteroaryl group, or a aralkyl group,
R3 and R4 represent a hydrogen atom, a C1 to C6 alkyl group, a halogen atom, or a C1 to C6 alkoxy group,
X represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, a C2 to C6 alkenyl group, a C2 to C6 alkynyl group, an aryl group, a heteroaryl group, or a C1 to C6 alkoxy group,
Y represents a hydrogen atom a halogen atom, a C1 to C6 alkyl group, or a C1 to C 6 alkoxy group, and
n represents 0 to 4, and m represents 0 to 6]




[in the formula (V), R1 represents an alkyl group and the like, R2 and R3 each independently represent a hydrogen atom, a haloalkyl group and the like (however, at least one of R2 and R3 is a haloalkyl group having 1 to 6 carbon atoms), A represents —OR4, —SR5, —NR6R7 or —NR8NR9R10, R4 represents an alkyl group having 3 to 12 carbon atoms, R5 represents an alkyl group having 1 to 12 carbon atoms, R6 represents a hydrogen atom, R7 represents an alkyl group having 5 to 12 carbon atoms, and R8, R9 and R10 each represent an alkyl group having 3 to 12 carbon atoms and the like, an alkyl group having 1 to 12 carbon atoms and the like, a hydrogen atom and the like, an alkyl group having 5 to 12 carbon atoms and the like, and an alkyl group having 1 to 12 carbon atoms, respectively.]
More preferred examples of other fungicides which may be mixed with the novel iminopyridine derivative represented by Formula (I) include azoxystrobin, orysastrobin, thifluzamide, furametpyr, fthalide, probenazole, acibenzolar-S-methyl, tiadinil, isotianil, carpropamid, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, tebufloquin, simeconazole, validamycin, kasugamycin and pencycuron, and particularly preferred examples thereof include probenazole and tebufloquin.
Preferred examples of other pest control agents which may be mixed with the novel iminopyridine derivatives represented by Formula (I) also include herbicides such as lipid synthesis inhibitors, acetolactate synthesis inhibitors, photosystem inhibitors, protoporphyrinogen IX oxidation inhibitors, bleacher herbicides, amino acid synthesis inhibitors, dihydropteroate synthetase inhibitors, cell division inhibitors, very-long-chain fatty acid synthesis inhibitors, cellulose biosynthesis inhibitors, decoupling agents, auxin-like herbicides, auxin transport inhibitors, and the like. Specific examples here are alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-P-methyl, haloxyfop-P, haloxyfop-P-methyl ester, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate, ethyl dipropylthiocarbamat (EPTC), esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, trichloroacetic acid (TCA), thiobencarb, tiocarbazil, triallate, vernolate, sulfonylureas (amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl, and tritosulfuron), imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, triazolopyrimidine herbicides (chloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan, and pyroxsulam), bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, flucarbazone, flucarbazone-sodium, propoxycarbazon, propoxycarbazon-sodium, thiencarbazone, thiencarbazone-methyl, triazine herbicides (chlorotriazine, triazinones, triazindiones, methylthiotriazines, and pyridazinones (for example, ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometryn, propazine, simazin, simetryn, terbumeton, terbuthylazin, terbutryn, and trietazin)), arylureas (for example, chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, and thiadiazuron), phenylcarbamate esters (for example, desmedipham, karbutilat, phenmedipham, and phenmedipham-ethyl), nitrile herbicides (for example, bromofenoxim, bromoxynil and its salts and esters, and ioxynil and its salts and esters), uracils (for example, bromacil, lenacil, and terbacil), bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, propanil, inhibitors of the photosystem (such as diquat, diquat-dibromide, paraquat, paraquatdichloride, and paraquat dimethyl sulfate), acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, ozadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, pyrazolate, picolinafen, aclonifen, amitrole, clomazone, flumeturon, glyphosate and its salts, bialaphos, bialaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium, asulam, dinitroanilines (for example, benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, and trifluralin), phosphoramidate herbicides (for example, amiprophos, amiprophos-methyl, and butamifos), benzoic acid herbicides (for example, chlorthal and chlorthal-dimethyl), pyridines (for example, dithiopyr and thiazopyr), benzamides (for example, propyzamide and tebutam), chloroacetamides (for example, acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamide, pretilachlor, propachlor, propisochlor, and thenylchlor), oxyacetanilides (for example, flufenacet and mefenacet), acetanilides (for example, diphenamide, naproanilide, and napropamide), tetrazolinones (for example, fentrazamide), anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, chlorthiamid, dichlobenil, flupoxam, isoxaben, dinoseb, dinoterb, 4,6-dinitro-o-cresol (DNOC) and its salts, 2,4-D and its salts and esters, 2,4-B and its salts and esters, aminopyralid and its salts (for example, aminopyralid-tris(2-hydroxypropyl)ammonium) and esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr and its salts and esters, 2-methyl-4-chlorophenoxyacetic acid (MCPA) and its salts and esters, MCPA-thioethyl, 4-(2-methyl-4-chlorophenoxy)butyric acid (MCPB) and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, 2,3,6-trichlorobenzoic acid (TBA (2,3,6)) and its salts and esters, triclopyr and its salts and esters, aminocyclopyrachlor and its salts and esters, diflufenzopyr and its salts, naptalam and its salts, bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-methyl sulfate, dimethipin, disodium methanearsonate (DSMA), dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters.
Control agents for animal parasitic pests which may be mixed with the novel iminopyridine derivatives represented by Formula (I) can be exemplified by organophosphate ester compounds, carbamate-based compounds, nereistoxin derivatives, organochlorine compounds, pyrethroid-based compounds, benzoyl urea-based compounds, juvenile hormone-like compounds, molting hormone-like compounds, neonicotinoid-based compounds, sodium channel blockers for nerve cells, insecticidal macrocyclic lactones, γ-aminobutyric acid (GABA) antagonists, ryanodine receptor agonistic compounds, insecticidal ureas, and the like. More preferred specific examples include organophosphate esters such as dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenofos, pyraclofos, chlorpyrifos-methyl, diazinon, trichlorfon, tetrachlorvinphos, bromofenofos, cythioate, and fenthion; carbamate-based compounds such as methomyl, thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicarb, carbofuran, and benfuracarb; nereistoxin derivatives such as cartap and thiocyclam; organochlorine compounds such as dicofol and tetradifon; pyrethroid-based compounds such as allethrin, d•d-T allethrin, dl•d-T80 allethrin, pyrethrins, phenothrin, flumethrin, cyfluthrin, d•d-T80 prarethrin, phthalthrin, transfluthrin, resmethrin, cyphenothrin, pyrethrum extract, synepirin 222, synepirin 500, permethrin, tefluthrin, cypermethrin, deltamethrin, cyhalothrin, fenvalerate, fluvalinate, ethofenprox, and silafluofen; benzoyl urea-based compounds such as diflubenzuron, teflubenzuron, flufenoxuron, chlorfluazuron, and lufenuron; juvenile hormone-like compounds such as methoprene; molting hormone-like compounds such as chromafenozide; and other compounds such as amitraz, chlordimeform, fipronil, etoxazole, imidacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, thiacloprid, dinotefuran, spirodiclofen, pyriproxyfen, indoxacarb, spinosad, spinetoram, avermectin, milbemycin, metaflumizone, pyrafluprole, pyriprole, hydramethylnon, triazamate, sulfoxaflor, flupyradifurone, ivermectin, selamectin, moxidectin, doramectin, eprinomectin, milbemycin oxim, diethylcarbamazine citrate, deet, metoxadiazon, cyromazine, triflumuron, star anise oil, triclabendazole, flubendazole, fenbendazole, antimony sodium gluconate, levamisole hydrochloride, bithionol, dichlorofen, phenothiazine, piperazine carbon bisulfide, piperazine phosphate, piperazine adipate, piperazine citrate, melarsomine dihydrochloride, metyridine, santonin, pyrantel pamoate, pyrantel, praziquantel, febantel, emodepside, derquantel, monopantel, emamectin benzoate, cycloxaprid, and a compound represented by the following Formula (VI) or agriculturally and zootechnically acceptable acid addition salts thereof. Examples of those acid addition salts include hydrochloride, nitrate, sulfate, phosphate, or acetate and the like.
More preferred examples are flumethrin, permethrin, fipronyl, pyriprol, imidacloprid, thiamethoxam, acetamiprid, dinotefuran, amitraz, metaflumizon, pyriproxyfen, fenitrothion, lufenuron, ethoxazol, spinosad, spinetoram, emodepside, emamectin benzoate, ivermectin, selamectin, moxidectin, doramectin, eprinomectin, derquantel, and monopantel.
Particularly preferred examples include amitraz and the like.
When the pest control composition is a pest control agent for agricultural and horticultural, particularly preferred examples for the present invention are pest control compositions in which the novel iminopyridine derivative represented by Formula (I) is at least one compound selected from N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P212), N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (compound 1-20), or N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide (compound 1-45), and the other pest control agent includes at least one insecticide or fungicide selected from acetamiprid, imidacloprid, clothianidin, dinotefuran, thiacloprid, fipronil, thiamethoxam, pymetrozine, flonicamid, spinosad, cyantraniliprole, chloranthraniliprole, ethofenprox, silafluofen, ethiprole, sulfoxaflor, flupyradifurone, flometoquin, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, and afidopyropen, orysastrobin, thifluzamide, furametpyr, fthalide, probenazole, acibenzolar-S-methyl, tiadinil, isotianil, carpropamid, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, tebufloquin, azoxystrobin, simeconazole, validamycin, thifluzamide, furametpyr, and pencycuron.
The pest control composition of the present invention may be prepared using the novel iminopyridine derivative represented by Formula (I), other insecticides, fungicides, herbicides, or control agents for animal parasites, and an agriculturally and zootechnically acceptable carrier (solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant, and other preparation adjuvants).
(Specific Examples of Pesticide Preparations)
When the pest control composition of the present invention is a pest control agent for agricultural and horticultural, the composition is usually mixed with an agriculturally and horticulturally acceptable carrier (solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant and other adjuvants for preparation to be provided in any formulation form of emulsifiable concentrates, liquid formulations, suspensions, wettable powders, flowables, dust, granules, tablets, oils, aerosols, fumigants and the like.
Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate and the like.
Examples of the liquid carrier include alcohols such as methanol, n-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane, kerosene and lamp oil, aromatic hydrocarbons such as toluene, xylene and methyl naphthalene, ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyl nitrile, acid amides such as dimethylformamide and dimethylacetamide, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, water and the like.
Further, examples of the gaseous carrier include LPG, air, nitrogen, carbonic acid gas, dimethyl ether and the like.
As the surfactant or dispersant for emulsification, dispersion, spreading and the like, it is possible to use, for example, alkylsulfate esters, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydricalcohol esters, lignin sulfonates or the like.
In addition, as the adjuvant for improving the properties of the preparation, it is possible to use, for example, carboxymethylcellulose, gum arabic, polyethylene glycol, calcium stearate or the like.
The aforementioned solid carriers, liquid carriers, gaseous carriers, surfactants, dispersants and adjuvants may be used either alone or in combination, if necessary.
The content of active ingredients in the preparation is not particularly limited, but is usually in the range of 1 to 75% by weight for the emulsifiable concentrate, 0.3 to 25% by weight for the dust, 1 to 90% by weight for the wettable powder, and 0.5 to 10% by weight for the granular formulation.
The novel iminopyridine derivatives represented by Formula (I), a preparation including the same and a mixed formulation of other pest control agents with the same may be applied to pest insects, plants, plant propagation materials (for example, seeds, plant leaves and stems, roots, soil, water surface and materials for cultivation), rooms which require disturbing the invasion of pests and the like. The application thereof may be performed before and after the invasion of pests.
A pest control agent including at least one of the novel iminopyridine derivatives represented by Formula (I) may also be applied to genetically-modified crops.
In a preferred aspect thereof, examples of a pest control composition further including an agriculturally and horticulturally acceptable carrier include:
(1) a wettable powder composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 0.6 to 30% by weight of a wetting agent and a dispersant, and 20 to 95% by weight of an extender,
(2) a water dispersible granule composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 0.6 to 30% by weight of a wetting agent, a dispersant and a binder, and 20 to 95% by weight of an extender,
(3) a flowable composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 5 to 40% by weight of a dispersant, a thickener, an antifreeze, an antiseptic and an antifoaming agent, and 20 to 94% by weight of water,
(4) an emulsifiable concentrate composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 1 to 30% by weight of an emulsifier and an emulsion stabilizer, and 20 to 97% by weight of an organic solvent,
(5) a dust composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, and 70 to 99.8% by weight of an extender,
(6) a low drift dust composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, and 70 to 99.8% by weight of an extender,
(7) a microgranule fine composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 0.2 to 10% by weight of a solvent or binder, and 70 to 99.6% by weight of an extender,
(8) a granule composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 0.5 to 30% by weight of a granulation auxiliary (surfactant) and a binder, and 20 to 98% by weight of an extender, and
(9) a microcapsule composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 1 to 50% by weight of a covering agent, an emulsifier, a dispersant and an antiseptic, and 20 to 98% by weight of water. Preferably, examples thereof include compositions of (2), (3), (6) and (8).
(Specific Examples of Formulations for Animals)
When the pest control agent of the present invention is a control agent for animal parasitic pests, the agent is provided in the form of liquid formulations, emulsifiable concentrates, liquid drops, sprays, foam preparations, granules, fine granules, dust, capsules, pills, tablets, chewable formulations, injections, suppositories, creams, shampoos, rinses, resin agents, fumigants, poison baits and the like, and is particularly preferably provided in the form of liquid formulations and liquid drops. These forms can be prepared using the following pharmaceutically acceptable carriers.
The liquid formulation may also be blended with a typical adjuvant for preparation, such as an emulsifier, a dispersant, a spreading agent, a wetting agent, a suspending agent, a preservative and a propellant, and may also be blended with a typical film former. As the surfactant for emulsification, dispersion, spreading and the like, it is possible to use, for example, soaps, polyoxyalkylene alkyl (aryl) ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene fatty acid ester, higher alcohols, alkyl aryl sulfonates and the like. Examples of dispersants include casein, gelatin, polysaccharides, lignin derivatives, saccharides, synthetic water soluble polymers and the like. Examples of spreading-wetting agents include glycerin, polyethylene glycol and the like. Examples of suspending agents include casein, gelatin, hydroxypropylcellulose, gum arabic and the like, and examples of stabilizers include phenolic antioxidants (BHT, BHA and the like), amine antioxidants (diphenylamine and the like), organic sulfur antioxidants and the like. Examples of preservatives include methyl p-oxybenzoate, ethyl p-oxybenzoate, propyl p-oxybenzoate, butyl p-oxybenzoate and the like. The aforementioned carriers, surfactants, dispersants and adjuvants may be used either alone or in combination, if necessary. Furthermore, perfumes, synergists and the like may also be incorporated. The suitable content of the active ingredients in the pest control agent of the present invention is usually 1 to 75% by weight for the liquid formulation.
Examples of carriers used for the preparation of creams include non-volatile hydrocarbons (liquid paraffin and the like), lanolin hydrogenated fats and oils, higher fatty acids, fatty acid esters, animal and vegetable oils, silicone oils, water and the like. Further, emulsifiers, humectants, antioxidants, perfumes, borax and ultraviolet absorbers may also be used either alone or in combination, if necessary. Examples of emulsifiers include fatty acid sorbitan, polyoxyethylene alkyl ethers, and fatty acid polyoxyethylene and the like. The suitable content of the active ingredients in the pest control agent of the present invention is usually 0.5 to 75% by weight for the cream.
The capsules, pills or tablets may be used such that the active ingredients in the composition of the present invention are mixed with a carrier such as starch, lactose or talc, a disintegrator and/or a binder, such as magnesium stearate is added thereto, and, if necessary, the mixture is tableted.
Carriers for the preparation of injections need to be prepared as an aseptic solution, but the solution may contain other substances, for example, a salt or glucose enough to isotonicate the solution with blood. As available carriers, “injections need to be prepared as an aseptic solution. For injections, the solution may contain, for example, a salt or glucose enough to isotonicate the solution with blood. Examples of available carriers for the preparation of injections include esters such as fatty acid derivatives of glyceride, benzyl benzoate, isopropyl myristate and propylene glycol, and organic solvents such as N-methylpyrrolidone and glycerol formal. The content of the active ingredients in the pest control agent of the present invention is usually 0.01 to 10% by weight for the injection.
Examples of carriers for the preparation of resin agents include vinyl chloride polymers, polyurethane and the like. Plasticizers such as phthalic acid esters, adipic acid esters and stearic acid may be added to these bases, if necessary. After the active ingredients are kneaded into the base, the kneaded product may be molded by injection molding, extrusion molding, press molding and the like. In addition, the molded product may also be properly subjected to processes such as molding or cutting to form an ear tag for animals or insecticidal collar for animals.
Examples of carriers for toxic baits include bait substances and attraction substances (farina such as wheat flour and corn flour, starch such as corn starch and potato starch, saccharides such as granulated sugar, malt sugar and honey, food flavors such as glycerin, onion flavor and milk flavor, animal powders such as pupal powder and fish powder, various pheromones and the like). The suitable content of the active ingredients in the pest control agent of the present invention is usually 0.0001 to 90% by weight for the toxic bait.
The pest control composition according to the present invention may be used such that a preparation form prepared by independently including at least one of the novel iminopyridine derivative represented by Formula (I) as the active ingredient in the composition, or acid addition salts thereof and at least one of other pest control agents alone is formulated and these ingredients when used are mixed on the spot.
Therefore, according to another aspect of the present invention, there is provided a combined product prepared by including at least one of the novel iminopyridine derivative represented by Formula (I) as the active ingredient or acid addition salts thereof and at least one of other pest control agents.
According to another preferred aspect of the present invention, in the combined product, the novel iminopyridine derivative represented by Formula (I) or acid addition salts thereof is provided as a first composition prepared by including the same as active ingredients, and other pest control agents is provided as a second composition prepared by including the same as active ingredients. In this case, the first composition and the second composition may be any formulation form which uses appropriate carriers or adjuvants in combination thereof in the same manner as in the case of the aforementioned pest control composition. The combined product may be provided in the form of a pharmaceutical set.
According to still another aspect of the present invention, there is provided a method for protecting useful plants or animals from pests, including: simultaneously or independently (preferably, each ingredient simultaneously) applying at least one of the novel iminopyridine derivative represented by Formula (I), enantiomers thereof, mixtures thereof or acid addition salts thereof as an active ingredient and at least one of other pest control agents to a region to be treated.
In the method, “simultaneously” applying also includes mixing at least one of the novel iminopyridine derivative represented by Formula (I) or acid addition salts thereof and at least one of other pest control agents before being applied to a region to be treated, and applying the mixture thereto. “Independently” applying includes, without mixing these ingredients in advance, applying the novel iminopyridine derivative represented by Formula (I) or acid addition salts thereof earlier than the other ingredients, or applying the novel iminopyridine derivative represented by Formula (I) or acid addition salts thereof later than the other ingredients.
According to still another preferred aspect of the present invention,
there is provided a method for protecting useful plants or animals from pests, including: applying
(1) a first composition prepared by including at least one of the novel iminopyridine derivative represented by Formula (I) or acid addition salts thereof as an active ingredient, and
(2) a second composition prepared by including at least one of other pest control agents as an active ingredient
to a region to be treated.
According to yet another aspect of the present invention, there is provided a method for protecting useful plants from pests, including: applying the composition or combined product of the present invention as it is or diluted to pests, useful plants, seeds of useful plants, soil, cultivation carriers or animals as a target, and preferably to useful plants, soil or animals.
According to still yet another aspect of the present invention, there is provided a use of the composition or combined product of the present invention in order to protect useful plants or animals from pests.
Furthermore, preferred examples of the method for applying the composition or combined product of the present invention to pests, useful plants, seeds of useful plants, soil or cultivation carriers as a target include spray treatment, water surface treatment, soil treatment (mixing, irrigation and the like), nursery box treatment, surface treatment (application, dust coating and covering) or fumigation treatment (treatment in enclosed space, such as covering soil with a polyfilm after soil injection) and the like, and more preferred examples include water surface treatment, soil treatment, nursery box treatment or surface treatment.
The throughput in the case of application to plants by spray treatment is 0.1 g to 10 kg per 10 ares of cultivated land and preferably 1 g to 1 kg, as an amount of active ingredients of the composition of the present invention.
Further, examples of a method for treating seeds, roots, tubers, bulbs or rhizomes of plants include a dipping method, a dust coating method, a smearing method, a spraying method, a pelleting method, a coating method and a fumigating method for the seed. The dipping method is a method in which seeds are dipped in a liquid chemical solution, and the dust coating method is classified into a dry dust coating method in which a granular chemical is adhered onto dry seeds, and a wet dust coating method in which a powdery chemical is adhered onto seeds which have been slightly soaked in water. In addition, the smearing method is a method in which a suspended chemical is applied on the surface of seeds within a mixer and the spraying method is a method in which a suspended chemical is sprayed onto the surface of seeds. Furthermore, the pelleting method is a method in which a chemical is mixed with a filler and treated when seeds are pelleted together with the filler to form pellets having certain size and shape, the coating method is a method in which a chemical-containing film is coated onto seeds, and the fumigating method is a method in which seeds are sterilized with a chemical which has been gasified within a hermetically sealed container.
Examples of the preferred treatment method of the composition of the present invention include a dipping method, a dust coating method, a smearing method, a spraying method, a pelleting method and a coating method.
Further, the composition of the present invention may also be used to, in addition to seeds, germinated plants which are transplanted after germination or after budding from soil, and embryo plants. These plants may be protected by the treatment of the whole or a part thereof by dipping before transplantation.
The throughput in the case of application to seeds of plants is not particularly limited, but preferably 1 g to 10 kg and more preferably 100 g to 1 kg per 100 kg of seeds, as an amount of active ingredients of the composition of the present invention.
In addition, the method for application of the composition of the present invention to soil is not particularly limited, but preferred application methods are as follows.
Examples of the method include a method in which granules including the composition of the present invention are applied into soil or on soil. Particularly preferred soil application methods include spraying, stripe application, groove application, and planting hole application.
Furthermore, application by irrigating soil with a solution prepared by emulsifying or dissolving the composition of the present invention in water is also a preferred soil application method.
Besides these methods, examples of preferred soil application methods include application into a nutrient solution in nutrient solution culture systems such as solid medium culture, for example, hydroponic culture, sand culture, NFT (nutrient film technique), rock wool culture and the like for the production of vegetables and flowering plants, or application into a nursery box for paddy rice seedling (mixing with bed soil and the like). The compound of the present invention may be applied directly to artificial culture soil including vermiculite and a solid medium including an artificial mat for growing seedling.
The throughput of the composition of the present invention into water surface, a nursery box or soil is not particularly limited, but is 0.1 g to 10 kg of preferably active ingredients per 10 ares of cultivated land and preferably 1 g to 1 kg. Further, as the method for applying the composition or combined product of the present invention to an applied organism, it is possible to control pests by administering the pest control composition of the present invention into the applied organism either orally or by injection, wholly or partly administering the composition into the body surface of an applied animal, or mounting the pest control agent formulated into a resin preparation or sheet preparation on the applied organism. In addition, it is also possible to control pests by covering places in which the invasion, parasitism and movement of pests are expected with the pest control composition of the present invention.
The pest control composition of the present invention may be used as it is, but may be diluted with water, liquid carriers, commercially available shampoos, rinses, baits, breed cage bottoms and the like and applied in some cases. When the pest control composition of the present invention is diluted with a dilution liquid (water) such as an emulsifiable concentrate, a flowable and a wettable powder and used, the amount is not particularly limited, but, preferably, the composition is applied by diluting the composition in water and spraying the mixture such that the concentration of active ingredients is 10 to 10,000 ppm. Furthermore, when the pest control composition of the present invention is administered to a target organism, the administration amount thereof is not particularly limited, but when the composition is percutaneously applied, the amount of the composition is preferably in a range from 0.01 to 500 mg per 1 kg of the body weight of the target organism. When the composition is orally administered, the amount of the composition is in a range from 0.01 to 100 mg per 1 kg of the body weight of the target organism. When a resin preparation is mounted on the target organism, the amount of the composition contained in the resin preparation is preferably in a range from 0.01 to 50% by weight per weight of the resin preparation.


EXAMPLES
Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited to the Examples.
Synthetic Example P1
N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P212)
(1) 25 g (270 mmol) of 2-aminopyridine was dissolved in 200 ml of anhydrous dichloromethane, 41 ml (30 g, 300 mmol) of triethylamine was added thereto, and the mixture was cooled to 0° C. 38 ml (57 g, 270 mmol) of anhydrous trifluoroacetic acid was added dropwise thereto over 15 minutes, and the resulting mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was injected into about 100 ml of iced water, and the mixture was stirred for 10 minutes. The mixture was transferred to a separatory funnel to perform liquid separation, and the organic layer was washed twice with 150 ml of water and twice with 150 ml of a 1% HCl aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 36 g (yield 71%) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide.
1H-NMR (CDCl3, δ, ppm): 7.20 (1H, ddd), 7.83 (1H, td), 8.20 (1H, d), 8.35 (1H, d), 10.07 (1H, brs)
13C-NMR (CDCl3, δ, ppm): 115.3, 115.5 (q), 121.6, 139.1, 147.9, 149.5, 155.3 (q)
MS: m/z=191 (M+H)
(2) 20 g (126 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 200 ml of anhydrous acetonitrile, 24 g (126 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the above-described method and 21 g (151 mmol) of potassium carbonate were added thereto, and the resulting mixture was heated and refluxed for 6 hours, and then stirred at room temperature for 10 hours. After the reaction was completed, the reaction solution was filtered and the liquid was concentrated under reduced pressure. Diethyl ether was added thereto for crystallization, and the crystals thus obtained were collected and washed well with diethyl ether and water. The crystals thus obtained were dried under reduced pressure at 60° C. for 1 hour to obtain the subject material. Amount obtained 26 g (yield 66%).
1H-NMR (CDCl3, δ, ppm): 5.57 (2H, s), 6.92 (1H, td), 7.31 (1H, d), 7.80 (1H, td), 7.87 (1H, dd), 7.99 (1H, dd), 8.48 (2H, m)
13C-NMR (CDCl3, δ, ppm): 53.8, 115.5, 117.2 (q), 122.1, 124.7, 130.0, 139.2, 140.0, 142.5, 149.7, 151.8, 158.9, 163.5 (q)
MS: m/z=316 (M+H)
(3) Powder X-ray crystal analysis
In the powder X-ray diffraction, measurement was performed under the following conditions.
Device name: RINT-2200 (Rigaku Corporation)
X-ray: Cu-Kα (40 kV, 20 mA)
Scanning range: 4 to 400, sampling width: 0.02° and scanning rate: 1°/min
The results are as follows.
Diffraction angle (2θ) 8.7°, 14.2°, 17.5°, 18.3°, 19.8°, 22.4°, 30.9° and 35.3°
(4) Differential Scanning Calorimetry (DSC)
In the differential scanning calorimetry, measurement was performed under the following conditions.
Device name: DSC-60
Sample cell: aluminum
Temperature range: 50° C. to 250° C. (heating rate: 10° C./min)
As a result, the melting point was observed at 155° C. to 158° C.
Another Method of Synthetic Example P1
3.00 g (18.6 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 20 ml of anhydrous DMF, 1.75 g (18.6 mmol) of 2-aminopyridine was added thereto, and the resulting mixture was stirred at 80° C. for 8 hours and at room temperature for 5 hours. After the reaction was completed, DMF was distilled off under reduced pressure, acetonitrile was added thereto to precipitate a solid, and the solid was collected, washed well with acetonitrile and dried to obtain 2.07 g (yield 44%) of 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride.
1H-NMR (DMSO-d6, δ, ppm): 5.65 (2H, s), 6.96 (1H, t), 7.23 (1H, m), 7.57 (1H, d), 7.80 (1H, m), 7.91 (1H, m), 8.28 (1H, m), 8.49 (1H, d), 9.13 (2H, brs)
50 mg (0.20 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the above-described method was dissolved in 5 ml of anhydrous dichloromethane, 122 mg (1.00 mmol) of DMAP and 50 mg (0.24 mmol) of anhydrous trifluoroacetic acid were added thereto in sequence under ice cold conditions, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed with 1% hydrochloric acid, and then dried over anhydrous magnesium sulfate. Dichloromethane was distilled off under reduced pressure to obtain the subject material. Amount obtained 42 mg (yield 67%). NMR was the same as that of the above-described method.
Synthetic Example P2
2,2-dibromo-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide (Compound P241)
200 mg (0.78 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1, 238 mg (1.95 mmol) of DMAP and 224 mg (1.17 mmol) of EDC-HCl were dissolved in 10 ml of anhydrous dichloromethane, 101 μl (202 mg, 1.17 mmol) of dibromoacetic acid was added thereto, and the resulting mixture was stirred at room temperature overnight. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with a 1% HCl aqueous solution, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the subject material. Amount obtained 50 mg (yield 15%)
1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 5.99 (1H, s), 6.78 (1H, td), 7.33 (1H, d), 7.69 (1H, td), 7.76 (1H, dd), 7.93 (1H, dd), 8.39 (1H, d), 8.50 (1H, d)
13C-NMR (CDCl3, δ, ppm): 44.6, 53.1, 113.7, 121.9, 124.8, 130.1, 138.2, 139.7, 141.2, 149.5, 152.0, 159.4, 172.2
MS: m/z=418 (M+H)
Synthetic Example P3
N-[1-((6-chloro-5-fluoropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P227)
4.00 g (27.6 mmol) of 2-chloro-3-fluoro-5-methyl pyridine was dissolved in 80 ml of carbon tetrachloride, 7.37 g (41.4 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed overnight. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 3.06 g (yield 51%) of 5-(bromomethyl)-2-chloro-3-fluoropyridine.
1H-NMR (CDCl3, δ, ppm): 4.45 (2H, s), 7.54 (1H, dd), 8.23 (1H, s)
50 mg (0.22 mmol) of the 5-(bromomethyl)-2-chloro-3-fluoropyridine obtained by the aforementioned method was dissolved in 5 ml of anhydrous acetonitrile, 42 mg (0.22 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide obtained by the method described in (1) of Reference Example 1 and 36 mg (0.26 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 7 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter insoluble materials, and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected, washed with diethyl ether, and then dried under reduced pressure in a desiccator to obtain the subject material. Amount obtained 29 mg (yield 40%).
1H-NMR (CDCl3, δ, ppm): 5.54 (2H, s), 6.89 (1H, td), 7.76 (1H, dd), 7.80 (1H, td), 7.85 (1H, d), 8.29 (1H, d), 8.57 (1H, d)
MS: m/z=334 (M+H)
Synthetic Example P4
N-[1-((6-fluoropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P229)
500 mg (4.50 mmol) of 2-fluoro-5-methyl pyridine was dissolved in 50 ml of carbon tetrachloride, 1.20 g (6.76 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 2.5 hours. After the reaction was completed, the reaction solution was returned to room temperature, and the solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 300 mg (yield 35%) of 5-bromomethyl-2-fluoropyridine.
57 mg (0.30 mmol) of the 5-bromomethyl-2-fluoropyridine obtained by the aforementioned method was dissolved in 10 ml of anhydrous acetonitrile, 57 mg (0.30 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide synthesized by the method described in (1) of Synthetic Example P1 and 69 mg (0.50 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter insoluble materials, and the filtrate was concentrated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→3:1) to obtain the subject material. Amount obtained 21 mg (yield 23%).
1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 6.89 (1H, td), 6.94 (1H, d), 7.79 (1H, td), 7.87 (1H, d), 8.03 (1H, m), 8.31 (1H, s), 8.54 (1H, d)
MS: m/z=300 (M+H)
Synthetic Example P5
N-[1-((6-bromopyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P231)
500 mg (2.92 mmol) of 2-bromo-5-methylpyridine was dissolved in 15 ml of carbon tetrachloride, 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 19 hours. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 143 mg (yield 20%) of 2-bromo-5-bromomethylpyridine.
1H-NMR (CDCl3, δ, ppm): 4.42 (2H, s), 7.47 (1H, d), 7.59 (1H, dd), 8.38 (1H, d)
70 mg (0.28 mmol) of the 2-bromo-5-bromomethylpyridine obtained by the aforementioned method was dissolved in 10 ml of anhydrous acetonitrile, 54 mg (0.28 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide synthesized by the method described in (1) of Synthetic Example P1 and 46 mg (0.34 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter insoluble materials, and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected, washed with diethyl ether, and then dried under reduced pressure in a desiccator to obtain the subject material. Amount obtained 81 mg (yield 82%).
1H-NMR (CDCl3, δ, ppm): 5.52 (2H, s), 6.88 (1H, t), 7.48 (1H, d), 7.78 (2H, m), 7.84 (1H, d), 8.44 (1H, d), 8.53 (1H, d)
MS: m/z=360 (M+H)
Synthetic Example P6
2-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide (Compound P236)
70 mg (0.27 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1 was dissolved in 4 ml of anhydrous dichloromethane, 82 mg (0.67 mmol) of DMAP, 25 mg (0.27 mmol) of chloroacetic acid and 62 mg (0.32 mmol) of EDC-HCl were added thereto in sequence, and the resulting mixture was stirred at room temperature overnight. After the reaction was completed, dichloromethane was added thereto to dilute the mixture, and the mixture was washed with water and a 1% HCl aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the subject material. Amount obtained 4 mg (yield 5%).
1H-NMR (CDCl3, δ, ppm): 4.17 (2H, s), 5.46 (2H, s), 6.64 (1H, td), 7.31 (1H, d), 7.60 (1H, td), 7.64 (1H, dd), 7.80 (1H, dd), 8.32 (1H, d), 8.45 (1H, d)
MS: m/z=296 (M+H)
Synthetic Example P7
N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2-difluoroacetamide (Compound P238)
400 mg (4.26 mmol) of 2-aminopyridine was dissolved in 10 ml of anhydrous dichloromethane, 322 μl (490 mg, 5.11 mmol) of difluoroacetic acid, 982 mg (5.10 mmol) of EDC-HCl and 622 mg (5.11 mmol) of DMAP were added thereto, and the resulting mixture was stirred at room temperature for 61 hours. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with a 1% HCl aqueous solution, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 102 mg (yield 14%) of 2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide.
1H-NMR (CDCl3, δ, ppm): 6.03 (1H, t), 7.15 (1H, m), 7.78 (1H, td), 8.20 (1H, d), 8.34 (1H, dd), 8.72 (1H, brs)
100 mg (0.58 mmol) of the 2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the aforementioned method was dissolved in 10 ml of anhydrous acetonitrile, 94 mg (0.58 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 5 ml of anhydrous acetonitrile and added thereto, and subsequently, 84 mg (0.63 mmol) of potassium carbonate was added thereto and the resulting mixture was heated and refluxed for 140 minutes. After the reaction was completed, the reaction solution was returned to room temperature to filter off insoluble materials, and the filtrate was concentrated under reduced pressure. Ether was added thereto to precipitate a solid, and thus the solid was collected and dried well to obtain the subject material. Amount obtained 63 mg (yield 37%).
1H-NMR (CDCl3, δ, ppm): 5.52 (2H, s), 5.90 (1H, t), 6.79 (1H, td), 7.33 (1H, d), 7.71 (1H, m), 7.77 (1H, dd), 7.85 (1H, dd), 8.45 (1H, d), 8.50 (1H, d)
13C-NMR (DMSO-d6, δ, ppm): 53.0, 111.0 (t), 115.2, 120.7, 124.7, 131.7, 140.6, 141.6, 143.2, 150.4, 150.9, 158.3, 169.4 (t)
MS: m/z=298 (M+H)
Synthetic Example P8
2-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2-difluoroacetamide (Compound P239)
200 mg (2.13 mmol) of 2-aminopyridine was dissolved in 5 ml of dichloromethane, 491 mg (2.55 mmol) of EDC-HCl, 311 mg (2.55 mmol) of DMAP and 187 μl (2.23 mmol, 290 mg) of chlorodifluoroacetic acid were added thereto in sequence, and the resulting mixture was stirred overnight. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed with water and 1% hydrochloric acid, and then dried over anhydrous magnesium sulfate to obtain 105 mg (yield 24%) of 2-chloro-2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide.
1H-NMR (CDCl3, δ, ppm): 7.19 (1H, dd), 7.82 (1H, m), 8.18 (1H, d), 8.36 (1H, d), 9.35 (1H, brs)
53 mg (0.33 mmol) of 2-chloro-5-chloromethyl pyridine dissolved in 6 ml of anhydrous acetonitrile was added to 68 mg (0.33 mmol) of the 2-chloro-2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide synthesized by the aforementioned method, and subsequently, 50 mg (0.36 mmol) of potassium carbonate was added thereto and the resulting mixture was heated and refluxed for 1 hours. After the reaction was completed, the reaction solution was returned to room temperature and then concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected and dried to obtain the subject material. Amount obtained 49 mg (yield 45%).
1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 6.92 (1H, t), 7.33 (1H, d), 7.82 (1H, m), 7.91 (1H, dd), 8.02 (1H, d), 8.45 (1H, d), 8.48 (1H, d)
13C-NMR (CDCl3, δ, ppm): 53.8, 115.2, 120.1 (t), 122.1, 124.8, 139.0, 140.0, 142.3, 150.0, 151.9, 159.1, 159.1, 165.8 (t)
MS: m/z=332 (M+H)
Synthetic Example P9
2,2,2-trichloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide (Compound P235)
70 mg (0.27 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1 was dissolved in 4 ml of anhydrous dichloromethane, 94 μl (0.68 mmol, 68 mg) of triethylamine and 33 g (0.27 mmol, 49 mg) of trichloroacetyl chloride were added thereto in sequence, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, water was added thereto to stop the reaction and liquid separation was performed with dichloromethane and water. The organic layer was washed once with water and twice with 1% hydrochloric acid, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected and dried to obtain the subject material. Amount obtained 61 mg (yield 62%).
1H-NMR (CDCl3, δ, ppm): 5.59 (2H, s), 6.86 (1H, t), 7.32 (1H, d), 7.78 (1H, td), 7.91 (2H, m), 8.43 (1H, d), 8.50 (1H, d)
MS: m/z=364 (M+H)
Synthetic Example P10
N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,3,3-pentafluoropropanamide (Compound P242)
300 mg (3.19 mmol) of 2-aminopyridine was dissolved in 15 ml of anhydrous dichloromethane, 919 mg (4.78 mmol) of EDC-HCl, 583 mg (4.78 mmol) of DMAP and 397 μl (628 mg, 3.83 mmol) of pentafluoropropionic acid were added thereto in sequence, and the resulting mixture was stirred at room temperature overnight. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with 1% hydrochloric acid, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 85 mg (yield 11%) of 2,2,3,3,3-pentafluoro-N-(pyridin-2(1H)-ylidene)propanamide.
52 mg (0.32 mmol) of 2-chloro-5-chloromethyl pyridine dissolved in 8 ml of anhydrous acetonitrile and 49 mg (0.35 mmol) of potassium carbonate were added to 77 mg (0.32 mmol) of the 2,2,3,3,3-pentafluoro-N-(pyridin-2(1H)-ylidene)propanamide obtained by the aforementioned method, and the resulting mixture was heated and refluxed for 11 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter insoluble materials, and the filtrate was concentrated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=1:3) to obtain the subject material. Amount obtained 12 mg (yield 10%).
1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 6.90 (1H, td), 7.32 (1H, d), 7.79 (2H, m), 7.84 (1H, d), 8.43 (1H, d), 8.56 (1H, d)
MS: m/z=366 (M+H)
Synthetic Example P11
N-[1-((2-chloropyrimidin-5-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P243)
1.04 g (8.13 mmol) of 2-chloro-5-methyl pyrimidine was dissolved in 30 ml of carbon tetrachloride, 1.73 g (9.75 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 641 mg (yield 38%) of 5-bromomethyl-2-chloropyridine.
1H-NMR (CDCl3, δ, ppm): 4.42 (2H, s), 8.66 (2H, s)
104 mg (0.50 mmol) of the 5-bromomethyl-2-chloropyridine obtained by the aforementioned method was dissolved in 6 ml of anhydrous acetonitrile, 96 mg (0.50 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide obtained by the method described in (1) of Synthetic Example P1 and 76 mg (0.55 mmol) of potassium carbonate were added thereto, and the resulting mixture was heated and refluxed for 1 hour. After the reaction was completed, the reaction solution was returned to room temperature to filter off insoluble materials, and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected, washed with diethyl ether, and then dried under reduced pressure in a desiccator to obtain the subject material. Amount obtained 92 mg (yield 58%).
1H-NMR (CDCl3, δ, ppm): 5.54 (2H, s), 6.98 (1H, m), 7.87 (1H, m), 8.18 (1H, m), 8.48 (1H, m), 8.83 (2H, m)
13C-NMR (CDCl3, δ, ppm): 60.0, 115.6, 117.1 (q), 122.1, 127.5, 139.2, 142.9, 158.8, 160.3 (2C), 161.4, 163.8 (q)
MS: m/z=317 (M+H)
The compounds of P213 to P226, P228, P230, P232 to P234, P240 and P244 shown in the following Table were synthesized by the methods in accordance with Synthetic Examples P1 to P11.







TABLE 40













 












Com-




IR (KBr,


pound




v, cm−1)


No.
Ar
R1a
Y
1H-NMR (CDCl3, δ, ppm)
or MS





P212
6-chloro-
CF3
H
5.57 (2H, s), 6.92
m/z =



3-pyridyl


(1H, td), 7.31 (1H,
316






d), 7.80 (1H, td),
(M + H)






7.87 (1H, dd), 7.99







(1H, dd), 8.48 (2H, m)



P213
2-chloro-
CF3
H
5.61 (2H, s), 6.93
m/z = 



5-


(1H, dd), 7.68 (1H, s),
322



thiazolyl


7.83 (1H, td), 7.97
(M + H)






(1H, d), 8.53 (1H, d)



P214
6-chloro-
OCH3
H
3.74 (3H, s), 5.40
m/z = 



3-pyridyl


(2H, s), 6.45 (1H,
278






td), 7.29 (1H, d),
(M + H)






7.46 (2H, m), 7.73







(1H, dd), 8.12 (1H,







dd), 8.40 (1H, d)



P215
6-chloro-
CF3
5-Cl
5.53 (2H, s), 7.34
m/z = 



3-pyridyl


(1H, d), 7.71 (1H,
350






dd), 7.87 (1H, dd),
(M + H)






7.94 (1H, s), 8.49







(1H, d), 8.55 (1H, s)



P216 
6-chloro-
CF3
5-F
5.54 (2H, s), 7.34
m/z = 



3-pyridyl


(1H, d), 7.70 (1H, m),
334






7.80 (1H, m), 7.88
(M + H)






(1H, dd), 8.48 (1H,







d), 8.64 (1H, m)



P217
6-chloro-
CF3
4-Cl
5.49 (2H, s), 6.85
m/z = 



3-pyridyl


(1H, dd), 7.35 (1H,
350






d), 7.76 (1H, dd),
(M + H)






7.85 (1H, dd), 8.44







(1H, d), 8.62 (1H, s)



P218
2-chloro-
CF3
5-Cl
5.56 (2H, s), 7.68
m/z = 



5-


(1H, s), 7.74 (1H,
356



thiazolyl


dd), 7.84 (1H, d),
(M + H)






8.58 (1H, d)



P219
2-chloro-
CF3
5-F
5.60 (2H, s), 7.69
m/z = 



5-


(1H, s), 7.72 (1H,
340



thiazolyl


td), 7.86 (1H, m),
(M + H)






8.67 (1H, m)



P220
2-chloro-
CF3
4-Cl
5.58 (2H, s), 6.90
m/z = 



5-


(1H, d), 7.67 (1H, s),
356



thiazolyl


7.90 (1H, d), 8.61
(M + H)






(1H, s)



P221
6-chloro-
CF3
3-Me
2.31 (3H, s), 5.50
m/z = 



3-pyridyl


(2H, s), 6.98 (1H, m),
330






7.34 (1H, d), 7.73
(M + H)






(1H, dd), 7.77 (2H,







m), 8.42 (1H, d)



P222
6-chloro-
CF3
4-Me
2.40 (3H, s), 5.49
m/z = 



3-pyridyl


(2H, s), 6.70 (1H,
330






dd), 7.32 (1H, d),
(M + H)






7.70 (1H, d), 7.86







(1H, dd), 8.37 (1H,







s), 8.43 (1H, d)



P223
6-chloro-
CF3
5-Me
2.29 (3H, s), 5.52
m/z = 



3-pyridyl


(2H, s), 7.32 (1H, d),
330






7.62 (1H, s), 7.65
(M + H)






(1H, dd), 7.88 (1H,







dd), 8.46 (1H, d),







8.50 (1H, d)



P224
phenyl
CF3
H
5.58 (2H, s), 6.81
m/z = 






(1H, m), 7.37 (4H, m),
281






7.77 (2H, m), 8.50
(M + H)






(1H, d)



P225
4-chloro-
CF3
H
5.52 (2H, s), 6.85
m/z = 



phenyl


(1H, m), 7.30 (2H, d),
315






7.36 (2H, d), 7.75
(M + H)






(1H, td), 7.84 (1H,







d), 8.47 (1H, d)



P226
3-pyridyl
CF3
H
5.57 (2H, s), 6.86
m/z = 






(1H, m), 7.26-7.35
282






(2H, m), 7.78 (1H,
(M + H)






td), 7.86 (1H, m),







8.63 (2H, m), 8.67







(1H, d)



P227
6-chloro-
CF3
H
5.54 (2H, s), 6.89
m/z = 



5-fluoro-


(1H, td), 7.76 (1H,
334



3-pyridyl


dd), 7.80 (1H, td),
(M + H)






7.85 (1H, d), 8.29







(1H, d), 8.57 (1H, d)



P228
6-trifluoro-
CF3
H
5.62 (2H, s), 6.90
m/z = 



methyl-3-


(1H, t), 7.69 (1H,
350



pyridyl


d), 7.81 (1H, t),
(M + H)






7.88 (1H, d), 8.06







(1H, d), 8.56 (1H,







d), 8.78 (1H, s)



P229
6-fluoro-
CF3
H
5.56 (2H, s), 6.89
m/z = 



3-pyridyl


(1H, td), 6.94 (1H,
300






d), 7.79 (1H, td),
(M + H)






7.87 (1H, d), 8.03







(1H, m), 8.31 (1H,







s), 8.54 (1H, d)



P230
5,6-dichloro-
CF3
H
5.49 (2H, s), 6.89
m/z = 



3-pyridyl


(1H, t), 7.79-7.90
350






(2H, m), 8.04 (1H,
(M + H)






d), 8.37 (1H, d),







8.56 (1H, m)
















TABLE 41













 












Com-




IR (KBr,


pound




v, cm−1)


No.
Ar
R1a
Y
1H-NMR (CDCl3, δ, ppm)
or MS





P231
6-bromo-
CF3
H
5.52 (2H, s), 6.88
m/z =



3-pyridyl


(1H, t), 7.48 (1H, d), 
360






7.78 (2H, m), 7.84
(M + H)






(1H, d), 8.44 (1H, d),







8.53 (1H, d)



P232
6-chloro-
CF3
4-F
5.52 (2H, s), 6.71
m/z = 



3-pyridyl


(1H, m), 7.35 (1H, d),
334






7.86 (1H, dd), 7.94
(M + H)






(1H, m), 8.33 (1H,







dd), 8.44 (1H, d)



P233
6-chloro-
CF3
3-F
5.53 (2H, s), 6.74
m/z = 



3-pyridyl


(1H, m), 7.33 (1H, d),
334






7.87 (1H, dd), 8.07
(M + H)






(1H, m), 8.29 (1H,







dd), 8.45 (1H, d)



P234
6-chloro-
CHCl2
H
5.54 (2H, s), 6.02
m/z = 



3-pyridyl


(1H, s), 6.77 (1H, t),
330






7.32 (1H, m), 7.69
(M + H)






(1H, m), 7.77 (1H, d),







7.89 (1H, m), 8.42







(1H, m), 8.49 (1H, s)



P235 
6-chloro-
CCl3
H
5.59 (2H, s), 6.86
m/z = 



3-pyridyl


(1H, t), 7.32 (1H, d),
364






7.78 (1H, td), 7.91
(M + H)






(2H, m), 8.43 (1H, d),







8.50 (1H, d)



P236
6-chloro-
CH2Cl
H
4.17 (2H, s), 5.46
m/z = 



3-pyridyl


(2H, s), 6.64 (1H,
296






td), 7.31 (1H, d),
(M + H)






7.60 (1H, td), 7.64







(1H, dd), 7.80 (1H,







dd), 8.32 (1H, d),







8.45 (1H, d)



P238
6-chloro-
CHF2
H
5.52 (2H, s), 5.90
m/z = 



3-pyridyl


(1H, t), 6.79 (1H,
298






td), 7.33 (1H, d),
(M + H)






7.71 (1H, m), 7.77







(1H, dd), 7.85 (1H,







dd), 8.45 (1H, d),







8.50 (1H, d)



P239
6-chloro-
CF2Cl
H
5.56 (2H, s), 6.92
m/z = 



3-pyridyl


(1H, t), 7.33 (1H, d),
332






7.82 (1H, m), 7.91
(M + H)






(1H, dd), 8.02 (1H,







d), 8.45 (1H, d), 8.48







(1H, d)



P240
6-chloro-
CHClBr
H
5.53 (1H, d), 5.58
m/z = 



3-pyridyl


(1H, d), 6.06 (1H, s),
374






6.76 (1H, td), 7.32
(M + H)






(1H, d), 7.69 (1H, m),







7.70 (1H, m), 7.90







(1H, dd), 8.40 (1H,







d), 8.50 (1H, d)



P241
6-chloro-
CHBr2
H
5.56 (2H, s), 5.99
m/z = 



3-pyridyl


(1H, s), 6.78 (1H,
418






td), 7.33 (1H, d),
(M + H)






7.69 (1H, td), 7.76







(1H, dd), 7.93 (1H,







dd), 8.39 (1H, d),







8.50 (1H, d)



P242
6-chloro-
CF2C
H
5.56 (2H, s), 6.90
m/z = 



3-pyridyl
F 3

(1H, td), 7.32 (1H,
366






d), 7.79 (2H, m), 7.84
(M + H)






(1H, d), 8.43 (1H, d),







8.56 (1H, d)



P243
2-chloro-
CF3
H
5.54 (2H, s), 6.98
m/z = 



5-pyri-


(1H, m), 7.87 (1H, m),
317



midinyl


8.18 (1H, m), 8.48
(M + H)






(1H, m), 8.83 (2H, m)



P244
6-chloro-
CH2Br
H
4.17 (2H, s), 5.46




3-pyridyl


(2H, s), 6.63 (1H,







td), 7.31 (1H, d),







7.60 (1H, td), 7.65







(1H, dd), 7.80 (1H,







dd), 8.32 (1H, d),







8.47 (1H, d)









Synthetic Example 1
2,2-difluoro-N-[1-((6-fluoropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]acetamide (Compound 3-3)




(1) 400 mg (4.26 mmol) of 2-aminopyridine was dissolved in 10 ml of anhydrous dichloromethane, 322 μl (490 mg, 5.11 mmol) of difluoroacetic acid, 982 mg (5.10 mmol) of EDC-HCl and 622 mg (5.11 mmol) of DMAP were added thereto, and the resulting mixture was stirred at room temperature for 61 hours. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with a 1% HCl aqueous solution, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 102 mg (yield 14%) of 2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide.
1H-NMR (CDCl3, δ, ppm): 6.03 (1H, t), 7.15 (1H, m), 7.78 (1H, td), 8.20 (1H, d), 8.34 (1H, dd), 8.72 (1H, brs)
(2) 128 mg (0.75 mmol) of 5-bromomethyl-2-fluoropyridine was dissolved in 3 ml of anhydrous DMF, 116 mg (0.68 mmol) of 2,2-difluoro-N-[pyridin-2(1H)-ylidene]acetamide was dissolved in 3 ml of anhydrous DMF and added thereto, and subsequently, 103 mg (0.75 mmol) of potassium carbonate was added thereto and the resulting mixture was stirred at 65° C. for 2 hours. After the reaction was completed, the reaction solution was returned to room temperature, and ethyl acetate and water were added thereto to perform liquid separation. The organic layer was washed with 1% hydrochloric acid, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. A small amount of hexane and diethyl ether were added thereto to precipitate crystals, and thus the crystals were collected and dried to obtain the subject material. Amount obtained 50 mg (yield 26%).
Synthetic Example 2
N-[1-((6-chloropyridin-3-yl)methyl)pyrimidin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound 190-2)




(1) 300 mg (1.86 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 6 ml of anhydrous DMF, 118 mg (1.24 mmol) of 2-aminopyrimidine was added thereto, and the resulting mixture was stirred at 80° C. for 8 hours. After the reaction was completed, the reaction solution was returned to room temperature to distill off DMF under reduced pressure. Diethyl ether was added thereto, and thus crystallization was occurred on the wall surface of an eggplant flask. Diethyl ether was removed by decantation and dried well to obtain 1-((6-chloropyridin-3-yl)methyl)pyrimidin-2(1H)-imine hydrochloride. Amount obtained 107 mg (yield 34%)
(2) 71 mg (0.27 mmol) of the 1-((6-chloropyridin-3-yl)methyl)pyrimidin-2(1H)-imine hydrochloride obtained by the aforementioned method was suspended in 5 ml of anhydrous dichloromethane, 114 μl (0.83 mmol, 83 mg) of triethylamine and 53 μl (0.38 mmol) of trifluoroacetic anhydride were added thereto in sequence, and the resulting mixture was stirred at room temperature for 2 hours. After the reaction was completed, dichloromethane and water were added to the reaction solution to perform liquid separation, and the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. A small amount of diethyl ether was added thereto to precipitate crystals, and thus the crystals were collected, washed with a small amount of diethyl ether, and then dried to obtain the subject material. Amount obtained 24 mg (yield 28%).
Synthetic Example 3
2,2,2-trifluoroethyl-[1-((6-chloropyridin-3-yl)methyl)pyridin-(2H)-ylidene]carbamate (Compound 1-17)




(1) 3.00 g (18.6 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 20 ml of anhydrous DMF, 1.75 g (18.6 mmol) of 2-aminopyridine was added thereto, and the resulting mixture was stirred at 80° C. for 8 hours and at room temperature for 5 hours. After the reaction was completed, DMF was distilled off under reduced pressure, acetonitrile was added thereto to precipitate a solid, and the solid was collected, washed well with acetonitrile and then dried to obtain 2.07 g (yield 44%) of 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride.
1H-NMR (DMSO-d6, δ, ppm): 5.65 (2H, s), 6.96 (1H, t), 7.23 (1H, m), 7.57 (1H, d), 7.80 (1H, m), 7.91 (1H, m), 8.28 (1H, m), 8.49 (1H, d)
(2) 10 ml of anhydrous acetonitrile was added to 150 mg (0.66 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the aforementioned method, 177 mg (0.66 mmol) of 4-nitrophenyl(2,2,2-trifluoroethyl)carbamate and 200 mg (1.46 mmol) of potassium carbonate were added, and the resulting mixture was stirred at 50° C. for 2 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter off insoluble materials, and the filtrate was concentrated under reduced pressure. Dichloromethane and water were added thereto to perform liquid separation, and the organic layer was washed with 1% hydrochloric acid, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. A small amount of diethyl ether was added thereto to precipitate crystals, and thus the crystals were collected and dried well to obtain the subject material. Amount obtained 48 mg (yield 21%).
Synthetic Example 4
N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (Compound 1-20)




(1) 25 g (270 mmol) of 2-aminopyridine was dissolved in 200 ml of anhydrous dichloromethane, 41 ml (30 g, 300 mmol) of triethylamine was added thereto, and the mixture was cooled to 0° C. 38 ml (57 g, 270 mmol) of anhydrous trifluoroacetic acid was added dropwise thereto over 15 minutes, and the resulting mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was injected into about 100 ml of iced water, and the mixture was stirred for 10 minutes. The mixture was transferred to a separatory funnel to perform liquid separation, and the organic layer was washed twice with 150 ml of water and twice with 150 ml of a 1% HCl aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 36 g (yield 71%) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide.
1H-NMR (CDCl3, δ, ppm): 7.20 (1H, m), 7.83 (1H, m), 8.20 (1H, d), 8.35 (1H, d), 10.07 (1H, brs)
13C-NMR (CDCl3, δ, ppm): 115.3, 115.5 (q), 121.6, 139.1, 147.9, 149.5, 155.3 (q)
(2) 20 g (126 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 200 ml of anhydrous acetonitrile, 24 g (126 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the above-described method and 21 g (151 mmol) of potassium carbonate were added thereto, and the resulting mixture was heated and refluxed for 6 hours, and then stirred at room temperature for 10 hours. After the reaction was completed, the reaction solution was filtered and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto for crystallization, and the crystals thus obtained were collected and washed well with diethyl ether and water. The crystals thus obtained were dried under reduced pressure at 60° C. for 1 hour to obtain N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (P212). Amount obtained 26 g (yield 66%).
1H-NMR (CDCl3, δ, ppm): 5.57 (2H, s), 6.92 (1H, td), 7.31 (1H, d), 7.80 (1H, td), 7.87 (1H, dd), 7.99 (1H, dd), 8.48 (2H, m)
13C-NMR (CDCl3, δ, ppm): 53.8, 115.5, 117.2 (q), 122.1, 124.7, 130.0, 139.2, 140.0, 142.5, 149.7, 151.8, 158.9, 163.5 (q)
MS: m/z=316 (M+H)
(3) 180 ml of toluene was added to 16.3 g (36.7 mmol) of phosphorus pentasulfide, 6.72 g (63.4 mmol) of sodium carbonate was added thereto and the resulting mixture was stirred at room temperature for 5 minutes. 20.0 g (63.4 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide obtained by the above-described method was added thereto, and the resulting mixture was stirred at 50° C. for 19 hours. 150 ml of ethyl acetate was added to the reaction solution, the resulting mixture was stirred at 50° C. for 10 minutes, then insoluble materials were filtered off, and 250 ml of ethyl acetate was used to wash the mixture. The mixture was transferred to a separatory funnel, washed therein with 300 ml of a saturated sodium bicarbonate water and 200 ml of a saturated saline solution, and then concentrated under reduced pressure. 200 ml of water was added thereto to precipitate crystals. The mixture was stirred at room temperature for 1 hour, and then the crystals were collected, subjected to slurry washing twice with 150 ml of water and twice with 150 ml of hexane, and dried at 60° C. under reduced pressure for 2 hours to obtain the subject material. Amount obtained 19.5 g (yield 94%).
1H-NMR (CDCl3, δ, ppm): 5.48 (2H, s), 7.12 (1H, td), 7.34 (1H, d), 7.77 (1H, dd), 7.96 (1H, m), 8.05 (1H, dd), 8.45 (1H, d), 8.56 (1H, d)
MS: m/z=332 (M+H)
Synthetic Example 5
N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-methylacetimidamide (Compound 1-42)




150 mg (0.45 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (1-20) synthesized by the method in Synthetic Example 4 was dissolved in 5 ml of methanol, 105 μl (42 mg, 1.36 mmol) of methylamine (40% methanol solution) and 124 mg (0.45 mmol) of silver carbonate were added thereto, and the resulting mixture was stirred at 50° C. for 1 hour. After the reaction was completed, the reaction solution was returned to room temperature and subjected to suction filtration by using celite to remove insoluble materials. Ethyl acetate and water were added thereto to perform liquid separation, and the organic layer was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and purified with silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 81 mg (yield 56%).
Synthetic Example 6
N′-(aryloxy)-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetimidamide (Compound 1-507)




30 mg (0.09 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (1-20) synthesized by the method in Synthetic Example 4 was dissolved in 5 ml of ethanol, 50 mg (0.45 mmol) of 0-ally hydroxylamine hydrochloride, 62 μl (0.45 mmol, 45 mg) of triethylamine and 25 mg (0.09 mmol) of silver carbonate were added thereto, and the resulting mixture was stirred at 50° C. for 5 hours and 20 minutes. After the reaction was completed, the reaction solution was returned to room temperature to filter off insoluble materials. The filtrate was concentrated under reduced pressure to perform liquid separation with ethyl acetate and 1% hydrochloric acid, then the ethyl acetate layer was washed with a saturated saline solution, and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The ethyl acetate layer was purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 15 mg (yield 45%).
Synthetic Example 7
N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide (Compound 1-499)




25 ml of ethanol was added to 1.00 g (3.00 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (1-20) 1 synthesized by the method in Synthetic Example 4, 1.04 g (15.0 mmol) of hydroxylamine hydrochloride and 2.00 ml (1.50 g, 15.0 mmol) of triethylamine were added thereto in sequence, and the resulting mixture was stirred at 50° C. for 21.5 hours. After the reaction was completed, ethyl acetate and 1% hydrochloric acid were added to the reaction solution to perform liquid separation, and the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The organic layer was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 625 mg (yield 63%).
Synthetic Example 8
N-(benzoyloxy)-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetimidamide (Compound 1-519)




30 mg (0.09 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide (1-499) synthesized by the method in Synthetic Example 7 was dissolved in 3 ml of anhydrous acetonitrile, 24 μl (17 mg, 0.17 mmol) of triethylamine and 20 μg (22 mg, 0.17 mmol) of benzoyl chloride were added thereto in sequence, and the resulting mixture was stirred at room temperature for 10 minutes. After the reaction was completed, ethyl acetate and 1% hydrochloric acid were added to the reaction solution to perform liquid separation, and the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The organic layer was purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 26 mg (yield 67%).
Synthetic Example 9
N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-((propylcarbamoyl)oxy)acetimidamide (Compound 1-534)




5 ml of anhydrous acetonitrile was added to 11 mg (0.13 mmol) of normal propyl isocyanate, 40 mg (0.12 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide (1-499) synthesized by the method in Synthetic Example 7 and 4 mg (0.04 mmol) of potassium-t-butoxide were added thereto, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and ethyl acetate and a saturated saline solution were added thereto to perform liquid separation. The ethyl acetate layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure and purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane:ethyl acetate=1:3) to obtain the subject material. Amount obtained 16 mg (yield 32%).
Synthetic Example 10
Diisopropyl 1-((6-chloropyridin-3-yl)methyl)pyridyn-2(1H)-ylidenphospholamide trithioate (Compound 1-702)




4.0g (15.7 mmol) of 1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-imine hydrochloride obtained by the above-described method was suspended in 24.6 ml of dichloromethane, and under ice-cooling 1.35 ml of phosphorous trichloride over 10 mins, following 3.16 g (31.2 mmol) of triethylamine dissolved in 37 ml of dichloromethane was added thereto. After the mixture was stirred for 2 hours at room temperature, 499 mg (15.6 mmol) of sulfur was added to the mixture, and the mixture was stirred over night at room temperature. Under ice-cooling 3.16 g (31.2 mmol) of triethylamine, following 2.38 g (31.2 mmol) of 2-propanethiol dissolved in 10 ml of dichloromethane were added to the mixture, additionary the mixture was stirred for a day. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and was extracted by 100 ml of diethylether twice. The ether solution was concentrated under reduced pressure, and 2.49g of cruede compounds was obtained. 186 mg of crude compound was purified by a TLC plate (5 sheets of 0.5 mm plate, evolved with ethyl acetate to obtain the subject material (47 mg. yield 9%) and (1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene)phosphoramidothioic dichloride (19 mg. yield 5%).




(1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene)phosphoramidothioic dichloride
Synthetic Example 11
N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2 (1H)-ylidene]-1,1,1-trifluoromethanesulfinamide (Compound 1-703)




330 mg (2 mmol) of sodium trifluoromethanesulfonate was added by 2 ml of ethylacetate and 154 mg (1 mmol) of phosphorus oxychloride and stirred for 5 min at room temperature. And 220 mg (0.86 mmol) of 1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-imine hydrochloride obtained by the above-described method was added to the mixture, and stirred for 2 hours. After the reaction was completed, the reaction mixture was purified by silica-gel column chromatography (eluent ethylacetate:hexane=1:1) to obtain the subject material (115 mg. yield 39%)
The compounds shown in the following Table were prepared by the method in accordance with Synthetic Examples 1 to 11.














TABLE 42










Reaction




Compound


Base and

temperature,
Method
Yield


No.
Raw material 1
Raw material 2
the like
Solvent
Time
(Table)
(%)







266-2
69 mg (0.43 mmol) of
84 mg (0.43
71 mg (0.52
Acetonitrile
reflux, 20 h
A
32



2-chloro-5-
mmol) of 2,2,2-
mmol) of



(chloromethyl)pyridine
trifluoro-N-
potassium




(1,3,4-thiadiazol-
carbonate




2(3H)-ylidene))acetamide


444-2
56 mg (0.41 mmol) of
66 mg (0.34
56 mg (0.41
Acetonitrile
reflux, 20 h
A
21



2-chloro-5-
mmol) of 2,2,2-
mmol) of



(chloromethyl)thiazole
trifluoro-N-
potassium




(1,3,4-thiadiazol-
carbonate




2(3H)-ylidene))acetamide


190-2
71 mg (0.27 mmol) of
53 μl (0.38 mmol) of
53 μl (0.38
Dichloromethane
Room
B
28



1-((6-chloropyridin-
anhydrous
mmol) of

temperature,



3-yl)methyl)pyrimidin-
trifluoroacetic
triethylamine

1 h



2(1H)-imine
acid



hydrochloride


201-2
120 mg (0.47 mmol) of
99 μl (0.71
160 μl (1.17
Dichloromethane
Room
B
11



1-((6-chloropyridin-
mmol) of
mmol) of

temperature,



3-yl)methyl)pyrazin-
anhydrous
triethylamine

30 min



2(1H)-imine
trifluoroacetic



hydrochloride
acid


223-2
530 mg (2.07 mmol) of 2-
390 μl (2.79 mmol)
537 μl (2.79
Dichloromethane
Room
B
14



chloro-2-((6-chloropyridin-3-
of anhydrous
mmol) of

temperature,



yl)methyl)pyridazin-
trifluoroacetic acid
triethylamine

2 h



3(2H)-imine hydrochloride


146-2
113 mg (0.70 mmol) of 2-
145 mg (0.70 mmol)
116 mg (0.84
Acetonitrile
reflux, 13 h
A
15



chloro-5-
of 2,2,2-trifluoro-
mmol) of



(chloromethyl)pyridine
N-(3-hydroxypyridin-
potassium




2(1H)-
carbonate




ylidene))acetamide


224-2
190 mg (0.73 mmol) of 2-
168 μl (1.20 mmol)
220 μl (1.60
Dichloromethane
Room
B
16



((2-chlorothiazol-5-
of anhydrous
mmol) of

temperature,



yl)methyl)pyridazin-
trifluoroacetic acid
triethylamine

5 min



3(2H)-imine hydrochloride


102-2
116 mg (0.72 mmol) of 2-
155 mg (0.72 mmol)
109 mg (0.79
Acetonitrile
reflux, 8 h
A
22



chloro-5-
of N-(3-
mmol) of



(chloromethyl)pyridine
cyanopyridin-2(1H)-
potassium




ylidene))2,2,2-
carbonate




trifluoroacetamide


212-2
59 mg (0.37 mmol) of 2-
70 mg (0.37 mmol) of
55 mg (0.40
Acetonitrile
reflux, 7 h
A
32



chloro-5-
2,2,2-trifluoro-N-
mmol) of



(chloromethyl)pyridine
(pyrimidin-4(3H)-
potassium




ylidene))acetamide
carbonate


  1-20
20.0 g (63.4 mmol) of N-[1-
16.3 g (36.7 mmol) of
6.72 mg (63.4
Toluene
50° C.,
D
94



((6-chloropyridin-3-
phosphorus pentasulfide
mmol) of

19 h



yl)methyl)pyridin-2(1H)-

sodium



ylidene]-2,2,2-

carbonate



trifluoroacetamide


 12-2
78 mg (0.38 mmol) of 2-
73 mg (0.38 mmol) of 2,2,2-
58 mg (0.42
Acetonitrile
reflux, 3.5 h
A
44



chloro-4-
trifluoro-N-(pyridin-2(1H)-
mmol) of



(bromomethyl)pyridine
ylidene))acetamide
potassium





carbonate


213-2
79 mg (0.47 mmol) of 2-
90 mg (0.47 mmol) of 2,2,2-
72 mg (0.52
Acetonitrile
reflux, 12 h
A
42



chloro-5-
trifluoro-N-(pyrimidin-
mmol) of



(chloromethyl)thiazole
4(3H)-ylidene))acetamide
potassium





carbonate


  1-17
150 mg (0.66 mmol) of 1-
177 mg (0.66 mmol) of 4-
200 mg (1.46
Acetonitrile
50° C., 2 h
C
21



[(6-chloropyridin-3-
nitrophenyl(2,2,2-
mmol) of



yl)methyl]pyridin-2(1H)-
trifluoroethyl)carbamate
potassium



imine hydrochloride

carbonate


  1-18
150 mg (0.66 mmol) of 1-
184 mg (0.66 mmol) of 4-
200 mg (1.46
Acetonitrile
50° C., 2 h
C
30



[(6-chloropyridin-3-
nitrophenyl(1,1,1-
mmol) of



yl)methyl]pyridin-2(1H)-
trifluoropropan-2-
potassium



imine hydrochloride
yl)carbamate
carbonate


  1-19
150 mg (0.66 mmol) of
220 mg (0.66 mmol) of
200 mg (1.46
Acetonitrile
50° C., 3 h
C
27



1-[(6-chloropyridin-3-
1,1,1,3,3,3-hexafluoro-
mmol) of



yl)methyl]pyridin-2(1H)-
propan-2-yl(4-nitro-
potassium



imine hydrochloride
phenyl)carbamate
carbonate


 7-2
116 mg (0.72 mmol) of
137 mg (0.72 mmol) of
110 mg (0.80
Acetonitrile
reflux, 5 h
A
49



2-chloro-5-
2,2,2-trifluoro-N-
mmol) of



(chloromethyl)pyrazine
(pyridin-2(1H)-
potassium




ylidene))acetamide
carbonate


  1-13
200 mg (0.78 mmol) of
103 μl (1.17 mmol) of
EDC-HCl 225 mg
Dichloromethane
Room
B
21



1-[(6-chloropyridin-3-
2,2,2-trilfluoropropionic
(1.17 mmol),

temperature,



yl)methyl]pyridin 2(1H)-
acid
DMAP 238 mg

12 h



imine hydrochloride

(1.95 mmol)























TABLE 43










Reaction




Compound


Base and

temperature,
Method
Yield


No.
Raw material 1
Raw material 2
the like
Solvent
Time
(Table)
(%)






















168-2 
273 mg (1.70 mmol) of 2-
350 mg (1.70 mmol)
248 mg
DMF
65° C., 2 h
A
15



chloro-5-
of 2,2,2-trifluoro-
(1.80



(chloromethyl)pyridine
N-(5-
mmol) of




hydroxypyridin-
potassium




2(1H)-
carbonate




ylidene))acetamide


 1-21
23 mg (0.077 mmol) of N-
41 mg (0.092 mmol)
10 mg
THF
Room
D
49



[1-((6-chloropyridin-3-
of phosphorus
(0.092

temperature,



yl)methyl)pyridin-2(1H) -
pentasulfide
mmol) of

2 h



ylidene]-2,2-

sodium



difluoroacetamide

carbonate


 3-20
30 mg (0.10 mmol) of N-
49 mg (0.11 mmol)
12 mg
THF
Room
D
49



[1-((6-fluoropyridin-3-
of phosphorus
(0.11

temperature,



yl)methyl)pyridin-2(1H)-
pentasulfide
mmol) of

3 h



ylidene]-2,2,2-

sodium



trifluoroacetamide

carbonate


 4-20
30 mg (0.083 mmol) of N-
41 mg (0.09 mmol)
10 mg
THF
Room
D
61



[1-((6-bromopyridin-3-
of phosphorus
(0.09

temperature,



yl)methyl)pyridin-2(1H)-
pentasulide
mmol) of

3 h



ylidene]-2,2,2-

sodium



trifluoroacetamide

carbonate


3-3
116 mg (0.72 mmol) of 2-
116 mg (0.68 mmol)
110 mg
Acetonitrile
reflux, 6 h
A
27



fluoro-5-
of 2,2-difluoro-N-
(0.80



(bromomethyl)pyridine
(pyridin-2(1H)-
mmol) of




ylidene))acetamide
potassium





carbonate


4-3
50 mg (0.20 mmol) of 2-
35 mg (0.20 mmol) of
33 mg
Acetonitrile
reflux, 6 h
A
53



bromo-5-
2,2-difluoro-N-
(0.24



(bromomethyl)pyridine
(pyridin-2(1H)-
mmol) of




ylidene))acetamide
potassium





carbonate


5-5
46 mg (0.21 mmol) of 5-
50 mg (0.21 mmol) of
35 mg
Acetonitrile
reflux, 2 h
A
26



(bromomethyl)-2-chloro-
2,2,3,3,3-pentafluoro-N-
(0.25



3-fluoropyridine
(pyridin-2(1H)-
mmol) of




ylidene))propanamide
potassium





carbonate


6-5
43 mg (0.21 mmol) of 5-
50 mg (0.21 mmol) of
35 mg
Acetonitrile
reflux, 2 h
A
21



(bromomethyl)-2-
2,2,3,3,3-pentafluoro-N-
(0.25



chloropyrimidine
(pyridin-2(1H)-
mmol) of




ylidene))propanamide
potassium





carbonate


 1-22
37 mg (0.11 mmol) of 2-
49 mg (0.11 mmol) of
12 mg
THF
Room
D
31



chloro-N-[1-((6-chloropyridin-3-
phosphorus
(0.11

temperature,



yl)methyl)pyridin-2(1H)-
pentasulfide
mmol) of

4 h



ylidene]-2,2-

sodium



difluoroacetamide

carbonate


 1-23
31 mg (0.085 mmol) of N-
38 mg (0.085 mmol)
9 mg
THF
Room
D
59



[1-((6-chloropyridin-3-
of phosphorus
(0.0854

temperature,



yl)methyl)pyridin-2(1H)-
pentasulfide
mmol) of

4 h



ylidene]-2,2,3,3,3-

sodium



pentafluoropropanamide

carbonate


 5-20
36 mg (0.11 mmol) of N-
49 mg (0.11 mmol) of
12 mg
THF
Room
D
100



[1-((6-chloro-5-
phosphorus
(0.11

temperature,



fluoropyridin-3-
pentasulfide
mmol) of

4 h



yl)methyl)pyridin-2(1H)-

sodium



ylidene]-2,2,2-

carbonate



trifluoroacetamide


5-3
65 mg (0.29 mmol) of 5-
50 mg (0.29 mmol) of
48 mg
Acetonitrile
reflux, 3 h
A
38



(bromomethyl)-2-chloro-
2,2-difluoro-N-
(0.35



3-fluoropyridine
(pyridin-2(1H)-
mmol) of




ylidene))acetamide
potassium





carbonate


6-3
60 mg (0.29 mmol) of 5-
50 mg (0.29 mmol) of
48 mg
Acetonitrile
reflux, 3 h
A
37



(bromomethyl)-2-
2,2-difluoro-N-
(0.35



chloropyrimidine
(pyridin-2(1H)-
mmol) of




ylidene))acetamide
potassium





carbonate


8-2
73 mg (0.45 mmol) of 3-
97 mg (0.51 mmol) of
83 mg
DMF
65° C., 3 h
A
32



chloro-6-
2,2,2-trifluoro-N-
(0.60



(chloromethyl)pyridazine
(pyridin-2(1H)-
mmol) of




ylidene))acetamide
potassium





carbonate


5-4
54 mg (0.24 mmol) of 5-
50 mg (0.24 mmol) of
41 mg
Acetonitrile
reflux, 6 h
A
51



(bromomethyl)-2-chloro-
2-chloro-2,2-
(0.30



3-fluoropyridine
difluoro-N-(pyridin-
mmol) of




2(1H)-ylidene))acetamide
potassium





carbonate


4-4
60 mg (0.24 mmol) of 2-
50 mg (0.24 mmol) of
41 mg
Acetonitrile
reflux, 6 h
A
48



bromo-5-
2-chloro-2,2-
(0.30



bromomethylpyridine
difluoro-N-(pyridin-
mmol) of




2(1H)-ylidene))acetamide
potassium





carbonate


6-4
49 mg (0.24 mmol) of 5-
50 mg (0.24 mmol) of
41 mg
Acetonitrile
reflux, 6 h
A
55



(bromomethyl)-2-
2-chloro-2,2-
(0.30



chloropyrimidine
difluoro-N-(pyridin-
mmol) of




2(1H)-ylidene))acetamide
potassium





carbonate


4-5
65 mg (0.26 mmol) of 2-
50 mg (0.26 mmol) of
41 mg
Acetonitrile
reflux, 2 h
A
8



bromo-5-
2,2,3,3,3-pentafluoro-N-
(0.30



bromomethylpyridine
(pyridin-2(1H)-
mmol) of




ylidene))propanamide
potassium





carbonate























TABLE 44










Reaction




Compound


Base and

temperature,
Method
Yield


No.
Raw material 1
Raw material 2
the like
Solvent
Time
(Table)
(%)







2-20
70 mg (0.22 mmol) of N-
107 mg (0.24 mmol)
25 mg (0.24
THF
Room
D
11



[1-((2-chlorothiazol-5-
of phosphorus
mmol) of

temperature,



yl)methyl)pyridin-
pentasulfide
sodium

4 h



2(1H)-ylidene]-2,2,2-

carbonate



trifluoroacetamide


10-20 
130 mg (0.37 mmol) of
181 mg (0.41 mmol)
43 mg (0.41
THF
Room
D
93



2,2,2-trifluoro-N-[1-
of phosphorus
mmol) of

temperature,



((6-trifluoromethyl)pyridin-3-
pentasulfide
sodium

4 h



yl)methyl)pyridin-

carbonate



2(1H)-ylidene]-acetamide


3-4 
110 mg (0.58 mmol) of
105 mg (0.51 mmol)
103 mg (0.75
DMF
65° C., 2 h
A
63



2-fluoro-5-
of 2-chloro-2,2-
mmol) of



(bromomethyl)pyridine
difluoro-N-
potassium




(pyridin-2(1H)-
carbonate




ylidene))acetamide


3-5 
110 mg (0.58 mmol) of
139 mg (0.58 mmol)
88 mg (0.63
DMF
65° C., 2 h
A
22



2-fluoro-5-
of 2,2,3,3,3-pentafluoro-N-
mmol) of



(bromomethyl)pyridine
(pyridin-2(1H)-
potassium




ylidene)propanamide
carbonate


11-20 
40 mg (0.15 mmol) of
65 mg (0.11 mmol)
16 mg (0.15
THF
Room
D
53



2,2,2-trifluoro-N-[1-
of phosphorus
mmol) of

temperature,



((tetrahydrofuran-3-
pentasulfide
sodium

4 h



yl)methyl)pyridin-

carbonate



2(1H)-ylidene]acetamide


1-14
200 mg (0.78 mmol) of
76 μl (0.94 mmol)
32 μl (0.23
Acetonitrile
reflux, 1 h
B
28



1-[(6-chloropyridin-3-
of acrylic acid
mmol) of



yl)methyl]pyridin-
chloride
triethylamine



2(1H)-imine



hydrochloride


1-37
78 mg (0.28 mmol) of N-
125 mg (0.28 mmol)
30 mg (0.28
THF
Room
D
21



[1-((6-chloropyridin-3-
of phosphorus
mmol) of

temperature,



yl)methyl)pyridin-
pentasulfide
sodium

2 h



2(1H)-ylidene]-

carbonate



propionamide


1-39
180 mg (0.96 mmol) of
341 mg (0.75 mmol)
102 mg (0.96
THF
Room
D
29



N-[1-((6-chloropyridin-
of phosphorus
mmol) of

temperature,



3-yl)methyl)pyridin-
pentasulfide
sodium

2 h



2(1H)-ylidene]-

carbonate



isobutyramide


1-40
54 mg (0.19 mmol) of N-
54 mg (0.19 mmol)
20 mg (0.19
THF
Room
D
12



[1-((6-chloropyridin-3-
of phosphorus
mmol) of

temperature,



yl)methyl)pyridin-
pentasulfide
sodium

2 h



2(1H)-ylidene]-

carbonate



cyclopropane



carboxyamide


1-15
200 mg (0.78 mmol) of 1-
83 mg (0.94 mmol)
320 μl (2.34
Acetonitrile
reflux, 5 h
B
19



[(6-chloropyridin-3-
of propyol
mmol) of



yl)methyl]pyridin-2(1H)-
oxychloride
triethylamine



imine hydrochloride


1-35
26 mg (0.074 mmol) of N-
26 mg (0.06 mmol)
8 mg (0.074
THF
Room
D
23



[1-((6-chloropyridin-3-
of phosphorus
mmol) of

temperature,



yl)methyl)pyridin-2(1H)-
pentasulfide
sodium

1.5 h



ylidene]-3-

carbonate



phyenylpropanamide


 1-501
100 mg (0.30 mmol) of N-
145 mg (1.50 mmol)
205 μl (1.50
Ethanol
50° C., 19.5 h
F
14



[1-((6-chloropyridin-3-
of O-ethyl
mmol) of



yl)methyl)pyridin-2(1H)-
hydroxylamine
triethylamine



ylidene]-2,2,2-
hydrochloride



trifluoroethanethioamide


 1-499
1.00 g (3.00 mmol) of N-
1.04 g (15.0 mmol)
2.00 ml (15.0
Ethanol
50° C., 21 h
F
63



[1-((6-chloropyridin-3-
of hydroxylamine
mmol) of



yl)methyl)pyridin-2(1H)-
hydrochloride
triethylamine



ylidene]-2,2,2-



trifluoroethanethioamide


 1-510
1.00 g (3.00 mmol) of N-
239 mg (1.50 mmol)
205 μl (1.50
Ethanol
50° C., 19.5 h
F
20



[1-((6-chloropyridin-3-
of O-benzyl
mmol) of



yl)methyl)pyridin-2(1H)-
hydroxylamine
triethylamine



ylidene]-2,2,2-
hydrochloride



trifluoroethanethioamide


 1-511
30 mg (0.09 mmol) of N-
20 μl (0.28 mmol)
38 μl (0.28
Acetonitrile
Room
G
72



[1-((6-chloropyridin-3-
of acetyl chloride
mmol) of

temperature,



yl)methyl)pyridin-

triethylamine

15 min



2(1H)-ylidene]-2,2,2-



trifluoro-N′-



hydroxyacetimidamide























TABLE 45










Reaction




Compound


Base and

temperature,
Method
Yield


No.
Raw material 1
Raw material 2
the like
Solvent
Time
(Table)
(%)






















1-519
30 mg (0.09 mmol) of
20 μl (0.17
24 μl (0.17
Acetonitrile
Room
G
67



N-1-((6-chloropyridin-3-
mmol) of
mmol) of

temperature,



yl)methyl)pyridin-
benzoyl
triethylamine

10 min



2(1H)-ylidene]-2,2,2-
chloride



trifluoro-N′-



hydroxyacetimidamide


1-523
30 mg (0.09 mmol) of
20 μl (0.26
36 μl (0.26
Acetonitrile
Room
G
49



N-[1-((6-chloropyridin-3-
mmol) of methyl
mmol) of

temperature,



yl)methyl)pyridin-
chloroformate
triethylamine

20 min



2(1H)-ylidene]-2,2,2-



trifluoro-N′-



hydroxyacetimidamide


1-528
30 mg (0.09 mmol) of
20 μl (0.18
25 μl (0.18
Acetonitrile
Room
G
100



N-[1-((6-chloropyridin-3-
mmol) of
mmol) of

temperature,



yl)methyl)pyridin-
methanesulfonyl
triethylamine

20 min



2(1H)-ylidene]-2,2,2-
chloride



trifluoro-N′-



hydroxyacetimidamide


1-531
30 mg (0.09 mmol) of
28 mg (0.15
21 μl (0.15
Acetonitrile
Room
G
100



N-[1-((6-chloropyridin-3-
mmol) of 4-
mmol) of

temperature,



yl)methyl)pyridin-
methylbenzene-
triethylamine

12 h



2(1H)-ylidene]-
sufonyl chloride



2,2,2-trifluoro-N′-



hydroxyacetimidamide


1-507
30 mg (0.09 mmol) of
50 mg (0.45
62 μl (0.45
Ethanol
50° C., 5 h
F
45



N-[1-((6-chloropyridin-3-
mmol) of O-
mmol) of



yl)methyl)pyridin-
allyl
triethylamine,



2(1H)-ylidene]-
hydroxylamine
25 mg (0.09



2,2,2-trifluoroethanethioamide
hydrochloride
mmol) of silver





carbonate


1-516
30 mg (0.09 mmol) of
20 μl (0.25
34 μl (0.25
Acetonitrile
Room
G
64



N-[1-((6-chloropyridin-3-
mmol) of
mmol) of

temperature,



yl)methyl)pyridin-
acryloyl
triethylamine

20 min



2(1H)-ylidene]-
chloride



2,2,2-trifluoro-N′-



hydroxyacetimidamide


1-518
30 mg (0.09 mmol) of
15 mg (0.18
EDC-HCl 135 mg
Dichloromethane
Room
G
22



N-[1-((6-chloropyridin-3-
mmol) of 3-
(0.18 mmol),

temperature,



yl)methyl)pyridin-
butynoate
DMAP 22 mg(0.18

21 h



2(1H)-ylidene]-

mmol)



2,2,2-trifluoro-N′-



hydroxyacetimidamide


1-527
30 mg (0.09 mmol) of
20 μl (0.16
22 μl (0.16
Acetonitrile
Room
G
54



N-[1-((6-chloropyridin-3-
mmol) of phenyl
mmol) of

temperature,



yl)methyl)pyridin-
chloroformate
triethylamine

1.5 h



2(1H)-ylidene]-



2,2,2-trifluoro-N′-



hydroxyacetimidamide


1-521
30 mg (0.09 mmol) of
20 mg (0.14
40 μl (0.28
Acetonitrile
Room
G
46



N-[1-((6-chloropyridin-3-
mmol) of
mmol) of

temperature,



yl)methyl)pyridin-
nicotinic acid
triethylamine

1.5 h



2(1H)-ylidene]-
chloride



2,2,2-trifluoro-N′-
hydrochloride



hydroxyacetimidamide


1-43 
100 mg (0.30 mmol)
Ethylamine (30%
90 μl (0.60
Ethanol
50° C,. 1.5 h
E
57



of N-[1-(6-chloropyridin-3-
methanol
mmol) of



yl)methyl)pyridin-
solution, 0.60
triethylamine,



2(1H)-ylidene]-
mmol)
91 mg (0.33



2,2,2-

mmol) of silver



trifluoroethanethioamide

carbonate


1-536
50 mg (0.15 mmol) of
20 μl (0.17
tBuOK
Acetonitrile
Room
H
30



N-[1-((6-chloropyridin-3-
mmol) of benzyl
5 mg (0.04 mmol)

temperature,



yl)methyl)pyridin-
isocyanate


1 h



2(1H)-ylidene]-



2,2,2-trifluoro-N′-



hydroxyacetimidamide























TABLE 46










Reaction




Compound


Base and

temperature,
Method
Yield


No.
Raw material 1
Raw material 2
the like
Solvent
Time
(Table)
(%)







1-42 
150 mg (0.45 mmol) of N-
Methylamine
124 mg (0.45
Methanol
50°C, 1 h
E
56



[1-((6-chloropyridin-3-
(40% methanol
mmol) of



yl)methyl)pyridin-2(1H)-
solution,
silver



ylidene]-2,2,2-
1.36 mmol)
carbonate



trifluoroethanethioamide


1-500
50 mg (0.15 mmol) of N-
63 mg (0.75
103 μl (0.75
Ethanol
50° C., 5 h
F
50



[1-((6-chloropyridin-3-
mmol) of O-
mmol) of



yl)methyl)pyridin-2(1H)-
methyl
triethylamine,



ylidene]-2,2,2-
hydroxylamine
41 mg (0.15



trifluoroethanethioamide
hydrochloride
mmol) of





silver





carbonate


1-504
50 mg (0.15 mmol) of N-
95 mg (0.75
165 μl (1.20
Ethanol
50° C., 5 h
F
19



[1-((6-chloropyridin-3-
mmol) of O-t-
mmol) of



yl)methyl)pyridin-2(1H)-
butyl
triethylamine,



ylidene]-2,2,2-
hydroxylamine
62 mg (0.23



trifluoroethanethioamide
hydrochloride
mmol) of





silver





carbonate


1-534
40 mg (0.12 mmol) of N-
11 mg (0.13
tBuOK 4 mg
Acetonitrile
Room
H
32



[1-((6-chloropyridin-3-
mmol) of n-
(0.04 mmol)

temperature,



yl)methyl)pyridin-2(1H)-
propyl


1 h



ylidene]-2,2,2-trifluoro-
isocyanate



N′-hydroxyacetimidamide


1-535
40 mg (0.12 mmol) of N-
14 mg (0.13
tBuOK 4 mg
Acetonitrile
Room
H
54



[1-((6-chloropyridin-3-
mmol) of
(0.04 mmol)

temperature,



yl)methyl)pyridin-2(1H)-
chloroethyl


1 h



ylidene]-2,2,2-trifluoro-
isocyanate



N′-hydroxyacetimidamide


1-72 
150 mg (0.45 mmol) of N-
74 μl (0.68
137 mg (0.50
Ethanol
50° C., 3 h
E
45



[1-((6-chloropyridin-3-
mmol) of
mmol) of silver



yl)methyl)pyridin-2(1H)-
benzylamine
carbonate



ylidene]-2,2,2-



trifluoroethanethioamide


1-150
100 mg (0.30 mmol) of N-
56 μl (0.60
91 mg (0.33
Ethanol
50° C., 5 h
E
50



[1-((6-chloropyridin-3-
mmol) of
mmol) of silver



yl)methyl)pyridin-2(1H)-
methylthioethylamine
carbonate



ylidene]-2,2,2-



trifluoroethanethioamide


1-67 
100 mg (0.30 mmol) of N-
74 μl (1.20
91 mg (0.33
Ethanol
50° C., 2 h
E
49



[1-((6-chloropyridin-3-
mmol) of 2-
mmol) of silver



yl)methyl)pyridin-2(1H)-
aminoethanol
carbonate



ylidene]-2,2,2-



trifluoroethanethioamide


1-515
30 mg (0.09 mmol) of N-
40 μl (0.44
30 μl (0.22
Acetonitrile
50° C. 2 h
G
67



[1-((6-chloropyridin-3-
mmol) of
mmol) of



yl)methyl)pyridin-2(1H) -
cyclopropanecarboxylic
triethylamine



ylidene]-2,2,2-trifluoro-
acid chloride



N′-hydroxyacetimidamide


1-56 
100 mg (0.30 mmol) of N-
38 μl (0.60
91 mg (0.33
Ethanol
50° C., 2 h →
E
57



[1-((6-chloropyridin-3-
mmol) of
mmol) of silver

reflux, 2 h



yl)methyl)pyridin-2(1H)-
propargylamine
carbonate



ylidene]-2,2,2-



trifluoroethanethioamide


1-512
30 mg (0.09 mmol) of N-
20 μl (0.23
34 μl (0.25
Acetonitrile
Room
G
32



[1-((6-chloropyridin-3-
mmol) of
mmol) of

temperature,



yl)methyl)pyridin-2(1H)-
propionyl
triethylamine

30 min



ylidene]-2,2,2-trifluoro-
chloride



N′-hydroxyacetimidamide


1-514
30 mg (0.09 mmol) of N-
20 μl (0.19
27 μl (0.20
Acetonitrile
Room
G
61



[1-((6-chloropyridin-3-
mmol) of
mmol) of

temperature,



yl)methyl)pyridin-2(1H)-
isopropionyl
triethylamine

2 h



ylidene]-2,2,2-trifluoro-
chloride



N′-hydroxyacetimidamide


1-50 
100 mg (0.30 mmol) of N-
48 μl (1.20
91 mg (0.33
Ethanol
50° C., 1.5 h →
E
44



[1-((6-chloropyridin-3-
mmol) of
mmol) of silver

reflux, 4.5 h



yl)methyl)pyridin-2(1H)-
cyclopropylamine
carbonate



ylidene]-2,2,2-



trifluoroethanethioamide























TABLE 47










Reaction




Compound


Base and

temperature,
Method
Yield


No.
Raw material 1
Raw material 2
the like
Solvent
Time
(Table)
(%)







1-114
80 mg (0.30 mmol) of N-
48 μl (0.36 mmol) of
73 mg
Ethanol
50° C., 3.5 h
E
52



[1-((6-chloropyridin-3-
2-phenyloxyethylamine
(0.33



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-44 
80 mg (0.30 mmol) of N-
60 μl (0.72 mmol) of
73 mg
Ethanol
50° C., 2 h
E
55



[1-((6-chloropyridin-3-
n-propylamine
(0.33



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-118
100 mg (0.30 mmol) of N-
62 μl (0.60 mmol) of
91 mg
Ethanol
50° C., 5 h
E
70



[1-((6-chloropyridin-3-
2-aminomethylpyridine
(0.33



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-119
100 mg (0.30 mmol) of N-
62 μl (0.60 mmol) of
91 mg
Ethanol
50° C., 5 h
E
58



[1-((6-chloropyridin-3-
3-aminomethylpyridine
(0.33



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-47 
100 mg (0.30 mmol) of N-
44 mg (0.60 mmol) of
91 mg
Ethanol
50° C., 5 h
E
49



[1-((6-chloropyridin-3-
n-butylamine
(0.33



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-55 
100 mg (0.30 mmol) of N-
CH2═CHCH2NH2 34 mg
91 mg
Ethanol
50° C., 2 h →
E
53



[1-((6-chloropyridin-3-
(0.60 mmol)
(0.33

reflux, 1 h



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-122
100 mg (0.30 mmol) of N-
H2NCH2-(2-thienyl)
91 mg
Ethanol
50° C., 2 h →
E
30



[1-((6-chloropyridin-3-
68 mg (0.60 mmol)
(0.33

reflux, 1 h



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-45 
100 mg (0.30 mmol) of N-
70 mg (1.20 mmol) of
91 mg
Ethanol
50° C., 2 h →
E
35



[1-((6-chloropyridin-3-
isopropylamine
(0.33

reflux, 5 h



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-124
100 mg (0.30 mmol) of N-
H2NCH2-(2-furanyl)
91 mg
Ethanol
50° C., 2.5 h
E
56



[1-((6-chloropyridin-3-
58 mg (0.60 mmol)
(0.33



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-126
100 mg (0.30 mmol) of N-
H2NCH2-(2-
91 mg
Ethanol
50° C., 1 h
E
43



[1-((6-chloropyridin-3-
thienyldrofuranyl)
(0.33



yl)methyl)pyridin-2(1H)-
61 mg (0.60 mmol)
mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-64 
100 mg (0.30 mmol) of N-
110 mg (1.20 mmol)
91 mg
Ethanol
50° C., 1 h →
E
22



[1-((6-chloropyridin-3-
of aminoacetonitrile
(0.33

reflux, 6 h



yl)methyl)pyridin-2(1H)-
hydrochloride
mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-146
100 mg (0.30 mmol) of N-
CH3OCH2CH2NH2
91 mg
Ethanol
50° C., 5 h
E
30



[1-((6-chloropyridin-3-
45 mg (0.60 mmol)
(0.33



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-52 
100 mg (0.30 mmol) of N-
51 mg (0.60 mmol) of
91 mg
Ethanol
50° C., 4 h
E
30



[1-((6-chloropyridin-3-
cyclopentylamine
(0.33



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-121
100 mg (0.30 mmol) of N-
65 mg (0.60 mmol) of
91 mg
Ethanol
60° C., 4 h
E
33



[1-((6-chloropyridin-3-
4-aminomethyl
(0.33



yl)methyl)pyridin-2(1H)-
pyridine
mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate























TABLE 48










Reaction




Compound


Base and

temperature,
Method
Yield


No.
Raw material 1
Raw material 2
the like
Solvent
Time
(Table)
(%)







1-53
100 mg (0.30 mmol) of N-
59 mg (0.60 mmol) of
91 mg
Ethanol
60° C., 2 h
E
28



[1-((6-chloropyridin-3-
cyclohexylamine
(0.33



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


1-76
100 mg (0.30 mmol) of N-
73 mg (0.60 mmol) of
91 mg
Ethanol
60° C., 4 h
E
60



[1-((6-chloropyridin-3-
phenethylamine
(0.33



yl)methyl)pyridin-2(1H)-

mmol) of



ylidene]-2,2,2-

silver



trifluoroethanethioamide

carbonate


















TABLE 49







MS or IR


Compound

(KBr, v,


No.
1H-NMR (CDCl3, δ, ppm)
cm−1)







266-2  
5.62 (2H, s), 7.33 (1H, d), 7.83
m/z = 323



(1H, d), 8.57 (2H, m)
(M + H)


444-2  
5.73 (2H, s), 7.69 (1H, s), 8.56
m/z = 329



(1H, s)
(M + H)


190-2  
5.39 (2H, s), 6.87 (1H, dd),
m/z = 317



7.36 (1H, d), 7.91 (1H, dd),
(M + H)



8.39 (1H, d), 8.49 (1H, s), 8.79



(1H, d)


201-2  
5.45 (2H, s), 7.37 (1H, d), 7.65
m/z = 317



(1H, d), 7.87 (1H, dd), 7.99
(M + H)



(1H, d), 8.49 (1H, d), 9.80 (1H,



d)


223-2  
5.69 (2H, s), 7.31 (1H, d), 7.55
m/z = 317



(1H, dd), 7.92 (1H, dd), 8.28
(M + H)



(1H, dd), 8.59 (1H, d), 8.78



(1H, dd)


146-2  
5.64 (2H, s), 7.14 (1H, dd),
m/z = 332



7.33 (1H, d), 7.47 (1H, dd),
(M + H)



7.71 (1H, dd). 7.74 (1H, dd),



8.42 (1H, d), 11.64 (1H, br s)


224-2  
5.78 (2H, s), 7.57, 7.63 (1H,
m/z = 323



dd × 2), 7.70 (1H, s), 8.26, 8.41
(M + H)



(1H, dd × 2), 8.82, 9.04 (1H,



dd × 2)


102-2  
5.56 (2H, s), 7.15 (1H, m), 7.38
m/z = 341



(1H, d), 7.84 (1H, dd), 8.26
(M + H)



(1H, dd), 8.48 (1H, d), 8.60



(1H, d)


212-2  
5.43 (2H, s), 7.35 (1H, d), 7.87
m/z = 317



(1H, dd), 8.20 (1H, d), 8.29
(M + H)



(1H, d), 8.51 (1H, d), 8.77 (1H,



s)


1-20
5.48 (2H, s), 7.12 (1H, td),
m/z = 332



7.34 (1H, d), 7.77 (1H, dd),
(M + H)



7.96 (1H, m), 8.05 (1H, dd),



8.45 (1H, d), 8.56 (1H, d)


12-2 
5.54 (2H, s), 6.96 (1H, m), 7.21
m/z = 316



(1H, d), 7.87 (1H, m), 7.97 (1H,
(M + H)



m), 8.34 (1H, d), 8.50 (1H, d)


213-2  
5.51 (2H, s), 7.69 (1H, s), 8.25
m/z = 323



(1H, d), 8.30 (1H, d), 8.57 (1H,
(M + H)



s)


1-17
4.52 (2H, q), 5.44 (2H, s), 6.85
m/z = 346



(1H, td), 7.31 (1H, d), 7.57 (2H,
(M + H)



m), 7.79 (1H, dd), 8.14 (1H, d),



8.40 (1H, d)


1-18
1.44 (3H, d), 5.31 (1H, m), 5.42
m/z = 360



(2H, q), 6.54 (1H, td), 7.30 (1H,
(M + H)



d), 7.53 (2H, m). 7.79 (1H, dd),



8.10 (1H, d), 8.40 (1H, d)


1-19
5.47 (2H, s), 5.81 (1H, m), 6.69
m/z = 414



(1H, m), 7.31 (1H, d), 7.65 (1H,
(M + H)



m), 7.68 (1H, dd), 7.85 (1H, dd),



8.17 (1H, d), 8.40 (1H, d)


7-2 
5.57 (2H, s), 6.91 (1H, m), 7.80



(1H, m), 8.10 (1H, m), 8.47 (1H,



s), 8.49 (1H, d), 8.72 (1H, d)


1-13
3.22 (2H, q), 5.46 (2H, s), 6.65
m/s = 330



(1H, td), 7.31 (1H, d), 7.62 (lH,
(M + H)



m), 7.66 (1H, dd). 7.70 (1H, dd),



8.35 (1H, d), 8.41 (1H, d)


168-2  
5.11 (2H, s), 7.40 (2H, m), 7.75
m/z = 332.0426



(1H, dd), 8.09 (1H, d), 8.15 (1H,
(M + H)



d), 8.46 (1H, d), 8.81 (1H, br s)


1-21
5.49 (2H, s), 6.21 (1H, t), 7.05
m/z = 314.0346



(1H, td), 7.34 (1H, d), 7.82 (1H,
(M + H)



dd), 7.90 (1H, m), 7.94 (1H, dd),



8.45 (1H, d), 8.49 (1H, d)


3-20
5.51 (2H, s), 6.95 (1H, d), 7.15
m/z = 316.0559



(1H, td), 7.96 (2H, m), 8.09 (1H,
(M + H)



d), 8.29 (1H, d), 8.52 (1H, d)


4-20
5.47 (2H, s), 7.13 (1H, m), 7.50
m/z = 375.9



(1H, m), 7.66 (1H, m), 7.97 (1H,
(M + H)



m), 8.07 (1H, m), 8.43 (1H, s),



8.54 (1H, m)


3-3 
5.54 (2H, s), 5.92 (1H, t), 6.79



(1H, td), 6.94 (1H, dd), 7.70



(1H, m), 7.78 (1H, dd), 8.03 (1H,



td), 8.30 (1H, d), 8.50 (1H, d)


4-3 
5.50 (2H, s), 5.90 (1H, t), 6.79
m/z = 342



(1H, m), 7.48 (1H, d), 7.74 (3H,
(M + H)



m), 8.43 (1H, d), 8.50 (1H, d)


5-5 
5.56 (2H, s), 6.91 (1H, m), 7.69
m/z = 384.0372



(1H, dd), 7.82 (2H, m), 8.26 (1H,
(M + H)



d), 8.60 (1H, d)


6-5 
5.52 (2H, s), 6.93 (1H, m), 7.86
m/z = 367.0687



(2H, m). 8.61 (1H, d), 8.75 (2H,
(M + H)



s)


1-22
5.49 (2H, s), 7.09 (1H, td),
m/z = 347.9972



7.35 (1H, d), 7.78 (1H, dd),
(M + H)



7.95 (2H, m), 8.46 (1H, d), 8.55



(1H, d)


1-23
5.47 (2H, s), 7.10 (1H, td),
m/z = 382.0246



7.34 (1H, d), 7.68 (1H, dd),
(M + H)



7.95 (2H, m), 8.41 (1H, d), 8.55



(1H, dd)


5-20
5.49 (2H, s), 7.10 (1H, m), 7.65
m/z = 350.0188



(1H, dd), 7.96 (1H, m), 8.00
(M + H)



(1H, m), 8.27 (1H, d), 8.63 (1H,



d)


5-3 
5.53 (2H, s), 5.90 (1H, t), 6.80
m/z = 316.0507



(1H, td), 7.76 (2H, m), 8.29
(M + H)



(1H, d), 8.52 (1H, d)


















TABLE 50







MS or IR


Compound

(KBr, v.


No.
1H-NMR (CDCl3, δ, ppm)
cm−1)







6-3
5.45 (2H, s), 5.89 (1H, t), 6.83
m/z = 299.0532



(1H, td), 7.75 (1H, m), 7.82
(M + H)



(1H, dd), 8.52 (1H, d), 8.81



(2H, s)


8-2
5.73 (2H, s), 6.90 (1H, td),



7.54 (1H, d), 7.81 (1H, td),



7.97 (1H, d), 8.22 (1H, d), 8.53



(1H, d)


5-4
5.54 (2H, s), 6.86 (1H, td),
m/z = 350.0082



7.99 (3H, m). 8.30 (1H, d), 8.54
(M + H)



(1H, d)


4-4
5.52 (2H, s), 6.86 (1H, td),
m/z = 375.96



7.49 (1H, d), 7.77 (2H, m), 7.83
(M + H)



(1H, dd), 8.45 (1H, d), 8.52



(1H, d)


6-4
5.49 (2H, s), 6.90 (1H, td),
m/z = 333.0121



7.82 (1H, td), 7.87 (1H, dd),
(M + H)



8.54 (1H, d), 8.81 (2H, s)


4-5
5.53 (2H, s), 6.89 (1H, td),
m/z = 410



7.48 (1H, d), 7.70 (1H, dd),
(M + H)



7.82 (2H, m), 8.41 (1H, d), 8.58



(1H, d)


 2-20
5.57 (2H, s), 7.12 (1H, m), 7.68
m/z = 338



(1H, s), 7.97 (1H, m), 8.12 (1H,
(M + H)



d), 8.67 (1H, d)


10-20
5.58 (2H, s), 7.12 (1H, m), 7.70
m/z = 366



(1H, d), 7.97 (2H, m), 8.02 (1H,
(M + H)



d), 8.62 (1H, d), 8.77 (1H, s)


3-4
5.55 (2H, s), 6.86 (1H, td),
m/z = 316



6.95 (1H, dd), 7.77 (1H, td),
(M + H)



7.85 (1H, dd), 8.06 (1H, td),



8.31 (1H, d), 8.53 (1H, d)


3-5
5.56 (2H, s), 6.89 (1H, m), 6.94
m/z = 350



(1H, dd), 7.80 (2H, m), 7.97
(M + H)



(1H, td), 8.27 (1H, d), 8.58



(1H. d)


11-20
1.69 (1H, m), 2.07 (1H, m), 2.84
m/z = 291



(1H, m), 3.59 (1H, dd), 3.71
(M + H)



(1H, dd), 3.77 (1H, m), 3.96



(1H, m), 4.13 (1H, dd), 4.42



(1H, dd), 7.11 (1H, m), 7.92



(1H, dd), 7.98 (1H, m), 8.40



(1H, d)


 1-14
5.44 (2H, s), 5.61 (1H, dd),
m/z = 274



6.28 (1H, dd), 6.36 (1H, dd),
(M + H)



6.52 (1H, m), 7.30 (1H, d), 7.52



(1H, m), 7.57 (1H, d), 7.73 (1H,



dd), 8.28 (1H, d), 8.44 (1H, d)


 1-37
1.28 (3H, t), 2.88 (2H, q), 5.41
m/z = 292



(2H, s), 6.86 (1H, t), 7.35 (1H,
(M + H)



d), 7.75 (3H, m), 8.10 (1H, d),



8.44 (1H, d)


 1-39
1.26 (6H, d), 2.55 (1H, m), 5.51
m/z = 306



(2H, s), 6.98 (1H, m), 7.36 (1H,
(M + H)



d), 7.76 (1H, dd), 7.77 (2H, m),



8.08 (1H, d), 8.44 (1H, d)


 1-40
0.92 (2H, m), 1.22 (2H, m), 2.40
m/z = 304



(1H, m), 5.36 (2H, s), 6.77 (1H,
(M + H)



td), 7.34 (1H, d), 7.66 (2H, m),



7.71 (1H, dd), 8.14 (1H, d),



8.41 (1H, d)


 1-15
5.08 (2H, d), 5.40 (2H, s), 5.84
m/z = 286



(1H, t), 6.50 (1H, m), 7.30 (1H,
(M + H)



d), 7.50 (1H, m), 7.56 (1H, m),



7.80 (1H, dd), 8.25 (1H, d),



8.47 (1H, d)


 1-35
3.18 (4H, m), 5.05 (2H, s), 6.83
m/z = 368



(1H, td), 7.05 (1H, t), 7.25
(M + H)



(2H, m), 7.38 (3H, m), 7.59 (1H,



dd), 7.67 (1H, d), 7.72 (1H,



td), 7.99 (1H, d), 8.30 (1H, d)


 1-501
1.20 (3H, t), 4.10 (2H, q), 5.22
m/z = 359



(2H, s), 6.15 (1H, td), 6.27
(M + H)



(1H, d), 7.13 (1H, m), 7.27 (2H,



m), 7.79 (1H, dd), 8.37 (1H, d)


 1-499
5.26 (2H, s), 6.11 (1H, d), 6.31
m/z = 331



(1H, m), 7.31 (1H, m), 7.50 (1H,
(M + H)



d), 7.83 (1H, dd), 7.90 (1H,



dd), 8.44 (1H, d), 11.0 (1H, s)


 1-510
5.07 (2H, s), 5.19 (2H, s), 6.13
m/z = 421



(1H, td), 6.22 (1H, d), 7.07
(M + H)



(1H, m), 7.18-7.40 (8H, m), 7.69



(1H, dd), 8.34 (1H, d)


 1-511
1.99 (3H, s), 5.27 (2H, s), 6.37
m/z = 373



(2H, m), 7.31 (2H, m), 7.44 (1H,
(M + H)



dd), 7.76 (1H, dd), 8.37 (1H. d)


 1-519
5.31 (2H, s), 6.36 (1H, t), 6.51
m/z = 435



(1H, d), 7.17 (1H, d), 7.25 (4H,
(M + H)



m), 7.50 (3H, m), 7.78 (1H, dd),



8.41 (1H, d)


 1-523
3.84 (3H, s), 5.26 (2H, s), 6.35
m/z = 389



(1H, m), 6.40 (1H, d), 7.30 (2H,
(M + H)



m), 7.37 (1H, dd), 7.73 (1H,



dd), 8.37 (1H, d)


 1-528
3.14 (3H, s), 5.27 (2H, s), 6.44
m/z = 409



(1H, td), 6.54 (1H, dd), 7.32
(M + H)



(1H, d), 7.41 (2H, m), 7.68 (1H,



dd), 8.39 (1H, d)


 1-531
2.45 (3H, s), 5.23 (2H, s), 6.37
m/z = 485



(1H, d), 6.42 (1H, td), 7.29
(M + H)



(4H, m), 7.45 (1H, d), 7.70 (1H,



dd), 7.80 (2H, d), 8.35 (1H, d)


 1-507
4.54 (2H, m), 5.16 (2H, m), 5.22
m/z = 371



(2H, s), 5.91 (1H, m), 6.17 (1H,
(M + H)



td), 6.29 (1H, d), 7.15 (1H, m),



7.27 (2H, m), 7.79 (1H, dd),



8.37 (1H, d)


















TABLE 51







MS or IR


Compound

(KBr, v,


No.
1H-NMR (CDCl3, δ, ppm)
cm−1)







1-516
5.27 (2H, s), 5.76 (1H, dd), 5.91
m/z = 385



(1H, dd), 6.22 (1H, dd), 6.36 (1H,
(M + H)



m), 6.42 (1H, d), 7.29 (2H, m), 7.42



(1H, d), 7.76 (1H, dd), 8.37 (1H, d)


1-518
1.25 (1H, s), 1.98 (2H, s), 5.28
m/z = 397



(2H, s), 6.38 (2H, m), 7.30 (2H, m),
(M + H)



7.41 (1H, d), 7.75 (1H, dd), 8.38



(1H, d)


1-527
5.28 (2H, s), 6.39 (1H, m), 6.50
m/z = 451



(1H, d), 7.13 (1H, d), 7.22-7.41
(M + H)



(7H, m), 7.76 (1H, dd), 8.40 (1H, d)


1-521
5.30 (2H, s), 6.42 (1H, t), 6.52
m/z = 436



(1H, d), 7.20 (1H, d), 7.32 (2H, m),
(M + H)



7.53 (1H, dd), 7.75 (1H, dd), 8.01



(1H, dd), 8.41 (1H, d), 8.54 (1H,



d), 8.71 (1H, dd)


1-43 
1.13(3H, t), 3.03 (2H, q), 5.15 (2H,
m/z = 343



s), 6.12 (1H, m), 6.19 (1H, d),
(M + H)



7.14(1H, m), 7.27 (1H, m), 7.33 (1H,



d), 7.72 (1H, dd), 8.37 (1H, d)


1-536
4.48 (2H, d), 5.25 (2H, s), 6.36
m/z = 464



(1H, td), 6.41 (1H, d), 6.79 (1H,
(M + H)



m), 7.41 (7H, m), 7.73 (1H, dd),



8.40 (1H, d)


1-42 
2.86 (3H, s), 5.16 (2H, s), 6.15
m/z = 329



(2H, m), 7.16 (1H, m), 7.26 (1H,
(M + H)



dd), 7.31 (1H, d), 7.73 (1H, dd),



8.38 (1H, d)


1-500
3.86 (3H, s), 5.22 (2H, s), 6.17
m/z = 345



(1H, m), 6.26 (1H, d), 7.14 (1H, m),
(M + H)



7.23 (1H, dd), 7.30 (1H, d), 7.78



(1H, dd), 8.39 (1H, d)


1-504
1.23 ( 9H, s), 5.23 (2H, s), 6.10
m/z = 387



(1H, m), 6.22 (1H, d), 7.09 (1H, m),
(M + H)



7.20 (1H, dd), 7.26 (1H, m), 7.79



(1H, dd), 8.35 (1H, d)


1-534
0.95 (3H, t), 1.61 (2H, m), 3.23
m/z = 416



(2H, t), 5.24 (2H, s), 6.32 (1H, t),
(M + H)



6.39 (1H, d), 6.48 (1H, m), 7.33 (3H,



m), 7.74 (1H, dd), 8.40 (1H, d)


1-535
3.65 (4H, m), 5.25 (2H, s), 6.36
m/z = 436



(1H, t), 6.41 (1H, d), 6.82 (1H,
(M + H)



m), 7.36 (3H, m), 7.74 (1H, dd),



8.41 (1H, d)


1-72 
4.22 (2H, s), 5.13 (2H, s), 6.14
m/z = 405



(1H, m), 6.21 (1H, d), 7.13 (1H,
(M + H)



m), 7.26 (7H, m), 7.68 (1H, dd),



8.36 (1H, d)


1-150
2.08 (3H, s), 2.70 (2H, t), 3.22
m/z = 389



(2H, t), 5.15 (2H, s), 6.16 (1H,
(M + H)



t), 6.22 (1H, d), 7.17 (1H, m),



7.29 (1H, d), 7.33 (1H, d), 7.70



(1H, dd), 8.38 (1H, d)


1-67 
3.13 (2H, m), 3.73 (2H, t), 5.15
m/z = 359



(2H, s), 6.18 (2H, m), 7.17 (1H,
(M + H)



m), 7.33 (2H, m), 7.71 (1H, dd),



8.37 (1H, d)


1-515
0.82 (2H, m), 0.93 (2H, m), 1.40
m/z = 399



(1H, m), 5.27 (2H, s), 6.35 (1H,
(M + H)



m), 6.42 (1H, d), 7.31 (2H, m),



7.41 (1H, d), 7.77 (1H, dd),



8.38 (1H, d)


1-56 
2.13 (1H, t), 3.85 (2H, d), 5.18
m/z = 353



(2H, s), 6.21 (1H, t), 6.25 (1H,
(M + H)



d), 7.18 (1H, m), 7.29 (1H, d),



7.33 (1H, d), 7.70 (1H, dd),



8.38 (1H, d)


1-512
1.02 (3H, t), 2.23 (2H, q), 5.26
m/z = 387



(2 H, s), 6.34 (1H, m), 6.39 (1H,
(M + H)



m), 7.29 (2H, m), 7.40 (1H, d),



7.75 (1H, dd), 8.37 (1H, d)


1-514
0.97 (6H, s), 2.37 (1H, m), 5.26
m/z = 399



(2H, s), 6.35 (1H, m), 6.40 (1H,
(M + H)



d), 7.27 (2H, m), 7.42 (1H, dd),



7.77 (1H, dd), 8.38 (1H, d)


1-50 
0.74 (2H, m), 0.85 (2H, m), 2.51
m/z = 355



(1H, m), 5.18 (2H, s), 6.12 (1H,
(M + H)



m), 6.30 (1H, d), 7.15 (1H, m),



7.27 (1H, m), 7.31 (1H, d), 7.79



(1H, dd), 8.39 (1H, d)


1-114
3.44 (2H, td), 4.18 (2H, t),
m/z = 435



5.14 (2H, s), 6.15 (1H, td),
(M + H)



6.26 (1H, d), 6.86 (2H, d), 6.92



(1H, m), 7.16 (1H, m), 7.28 (4H,



m), 7.71 (1H, dd), 8.38 (1H, d)


1-44 
0.83 (3H, t), 1.55 (2H, m), 2.91
m/z = 357



(2H, m), 5.14 (2H, s), 6.12 (1H,
(M + H)



td), 6.18 (1H, d), 7.13 (1H, m),



7.30 (2H, m), 7.71 (1H, dd),



8.36 (1H, d)


1-118
4.41 (2H, s), 5.15 (2H, s), 6.18
m/z = 406



(1H, t), 6.24 (1H, d), 7.14 (2H,
(M + H)



m), 7.26 (2H, m), 7.54 (1H, d),



7.68 (1H, dd), 7.71 (1H, dd),



8.38 (1H, d), 8.47 (1H, d)


1-119
4.22 (2 H, s), 5.16 (2H, s), 6.20
m/z = 406



(2H, m), 7.15-7.30 (3H, m), 7.34
(M + H)



(1H, dd), 7.61 (1H, d), 7.79



(1H, dd), 8.37 (1H, d), 8.42



(1H, d), 8.46 (1H, d)


















TABLE 52







MS or IR


Compound

(KBr, v,


No.
1H-NMR (CDCl3, δ, ppm)
cm−1)







1-47
0.85 (3H, t), 1.25 (2H, m), 1.53
m/z = 371



(2H, m), 2.96 (2H, m), 5.14 (2H,
(M + H)



s), 6.10 (1H, m), 6.17 (1H, d),



6.99 (1H, m), 7.27 (2H, m), 7.70



(1H, dd), 8.36 (1H, d)


1-55
3.65 (2H, m), 5.04 (2H, m), 5.15
m/z = 355



(2H, s), 5.90 (1H, m), 6.13 (1H,
(M + H)



m), 6.20 (1H, d), 7.13 (1H, m),



7.28 (2H, m), 7.71 (1H, dd),



8.36 (1H, d)


 1-122
4.41 (2H, s), 5.17 (2H, s), 6.17
m/z = 411



(2H, m), 6.82 (1H, m), 6.91 (1H,
(M + H)



m), 7.16 (2H, m), 7.30 (2H, m),



7.70 (1H, dd), 8.38 (1H, d)


1-45
1.02 (6H, d), 3.34 (1H, m), 5.13
m/z = 357



(2H, s), 6.10 (1H, m), 6.24 (1H,
(M + H)



d), 7.11 (1H, m), 7.26 (1H, m),



7.31 (1H, d), 7.68 (1H, dd),



8.35 (1H, d)


 1-124
4.20 (2H, s), 5.17 (2H, s),
m/z = 395



6.13-6.29 (4H, m), 7.17 (1H, m),
(M + H)



7.30 (3H, m), 7.71 (1H, dd),



8.38 (1H, d)


 1-126
1.49 (1H, m), 1.84 (2H, m), 1.99
m/z = 399



(1H, m), 2.98 (1H, ddd), 3.14
(M + H)



(1H, ddd), 3.73 (2H, m), 4.09



(1H, m), 5.13 (2H, m), 6.13 (1H,



m), 6.20 (1H, d), 7.14 (1H, m),



7.30 (2H, m), 7.70 (1H, dd),



8.37 (1H, d)


1-64
4.01 (2H, s), 5.24 (2H, s), 6.34
m/z = 354



(2H, m), 7.34 (2H, m), 7.41 (1H,
(M + H)



dd), 7.66 (1H, dd), 8.36 (1H, d)


 1-146
3.21 (2H, m), 3.34 (2H, s), 3.57
m/z = 373



(2H, t), 5.14 (2H, s), 6.15 (1H,
(M + H)



m), 6.21 (1H, m), 7.15 (1H, m),



7.30 (2H, m), 7.72 (1H, dd),



8.37 (1H, d)


1-52
1.40-1.77 (8H, m), 3.48 (1H, m),
m/z = 383



5.12 (2H, s), 6.09 (1H, m), 6.23
(M + H)



(1H, d), 7.12 (1H, m), 7.24 (1H,



m), 7.31 (1H, d), 7.69 (1H, dd),



8.35 (1H, d)


 1-121
4.18 (2H, s), 5.14 (2H, s), 6.20
m/z = 406



(2H, m), 7.19 (3H, m), 7.26 (1H,
(M + H)



m), 7.35 (1H, dd), 7.75 (1H,



dd), 8.36 (1H, d), 8.51 (2H, m)


1-53
0.98-1.72 (10H, m), 2.91 (1H,
m/z = 397



m), 5.11 (2H, s), 6.11 (1H, td),
(M + H)



6.24 (1H, d), 7.11 (1H, m), 7.29



(3H, m), 7.66 (1H, dd), 8.34



(1H, d)


1-76
2.90 (2H, t), 3.24 (2H, td),
m/z = 419



5.07 (2H, s), 6.01 (1H, d), 6.09
(M + H)



(1H, td), 7.02-7.30 (8H, m),



7.61 (1H, dd), 8.34 (1H, d)


267-2  
4.34 (1H, d), 4.62 (1H, d), 6.40
1730, 1689,



(1H, d), 7.20 (1H, d), 7.51 (2H,
1556, 1467,



m), 7.59 (1H, dd), 7.63 (2H, m),
1440, 1418



7.82 (1H, d), 8.23 (1H, d)


253-2  
5.31 (2H, s), 7.28 (2H, m), 7.50
1644, 1557,



(1H, d), 7.72 (3H, m), 7.85 (1H,
1508, 1483



m), 8.25 (1H, d), 8.45 (1H, d)


251-2  
5.20 (2H, s), 7.26 (2H, m), 7.63
3065, 1696,



(2H, m), 7.85 (2H, m), 8.02 (1H,
1463, 1403



d), 8.23 (2H, m)


13-2 
5.76 (2H, s), 6.91 (1H, m), 7.46
3060, 2226,



(1H, m), 7.60 (1H, m), 7.70 (1H,
1641, 1556,



d), 7.80 (2H, m), 8.12 (1H, d),
1509



8.53 (1H, d)


1-1 
5.49 (2H, s), 6.67 (1H, m), 7.30
—



(1H, m), 7.60 (1H, m), 7.72 (2H,



m), 7.81 (1H, dd), 8.42 (1H, d),



9.06 (1H, s)


1-41
5.64 (2H, s), 7.50 (2H, m), 7.70
m/z = 315.16



(1H, d), 7.78 (1H, dd), 8.27
(M + H)



(1H, m), 8.37 (1H, d), 8.78 (1H,



d) (methanol-d4)


















TABLE 53







MS or IR


Compound

(KBr, v,


No.
1H-NMR (CDCl3, δ, ppm)
cm−1)







2-2 
2.47 (2H, m), 4.17 (2H, t), 5.07
m/z = 322



(1H, d), 5.15 (1H, dd), 5.39 (2H,
(M + H)



s), 5.85 (1H, m), 6.43 (1H, td),



7.30 (1H, d), 7.44 (2H, m), 7.75



(1H, dd), 8.08 (1H, d), 8.40 (1H, d)


1-647
2.47 (2H, m), 4.17 (2H, t), 5.07
m/z = 318.1013



(1H, d), 5.15 (1H, dd), 5.39 (2H,
(M + H)



s), 5.85 (1H, m), 6.43 (1H, td),



7.30 (1H, d), 7.44 (2H, m), 7.75



(1H, dd), 8.08 (1H, d), 8.40 (1H, d)


1-670
3.35(2H, tdd), 5.17 (2H, s), 6.02
m/z = 379



(1H, tt), 6.23 (2H, m), 7.22 (1H,
(M + H)



m), 7.33 (2H, m), 7.69 (1H, dd),



8.37 (1H, d)


157-2  
5.51 (2H, s), 6.63 (1H, dd), 7.42
m/z = 332



(1H, d), 7.77 (1H, d), 7.84 (1H,
(M + H)



dd), 8.26 (1H, d), 8.45 (1H, d)


1-10 
1.61 (1H, m), 2.29 (2H, m), 4.73
m/z = 324



(2H, s), 7.26 (1H, m), 7.31 (1H, m),
(M + H)



7.69 (1H, m), 7.79 (1H, m), 8.23



(1H, d), 8.40 (1H, d), 8.57 (1H, d)


580-2  
5.47 (2H, s), 6.89 (1H, m), 7.47
m/z = 332



(2H, m), 7.82 (2H, m), 8.41 (1H, s),
(M + H)



8.56 (1H, d)


1-671
0.87 (3H, t), 1.28 (10H, m), 1.55
m/z = 427



(2H, m), 2.96 (2H, t), 5.14 (2H, s),
(M + H)



6.13 (1H, t), 6.18 (1H, d), 7.13



(1H, m), 7.30 (2H, m), 7.71 (1H,



dd), 8.37 (1H, d)


1-658
0.87 (3H, t), 1.25 (26H, m), 1.55
m/z = 539



(2H, m), 2.96 (2H, t), 5.14 (2H, s),
(M + H)



6.11 (1H, t), 6.17 (1H, d), 7.13



(1H, m), 7.30 (2H, m), 7.70 (1H,



dd), 8.36 (1H, d)


1-659
0.87 (3H, t), 1.26 (18H, m), 1.53
m/z = 483



(2H, m), 2.95 (2H, t), 5.14 (2H, s),
(M + H)



6.12 (1H, t), 6.18 (1H, d), 7.13



(1H, m), 7.31 (2H, m), 7.71 (1H,



dd), 8.36 (1H, d)


1-660
0.74 (3H, t), 0.97 (3H, d), 1.42
m/z = 371



(2H, m), 3.08 (1H, m), 5.12 (2H,
(M + H)



dd), 6.09 (1H, t), 6.23 (1H, d),



7.11 (1H, m), 7.24 (1H, m), 7.30



(1H, d), 7.67 (1H, dd), 8.35



(1H, d)


1-681
0.77, 0.90 (6H, t × 2), 1.40 (4H,
m/z = 385



m), 2.97 (1H, m), 5.11 (2H, s),
(M + H)



6.10 (1H, t), 6.25 (1H, d), 7.11



(1H, m), 7.24 (1H, d), 7.32 (1H,



d), 7.66 (1H, dd), 8.34 (1H, d)


1-686
0.81, 0.91 (6H, t × 2), 1.02-1.45
m/z = 413



(8H, m), 3.19 (1H, m), 5.12 (2H,
(M + H)



s), 6.10 (1H, t), 6.25 (1H, d),



7.11 (1H, m), 7.22 (1H, d), 7.30



(1H, d), 7.64 (1H, dd), 8.33



(1H, d)


1-661
0.81 (3H, t), 0.97 (3H, d),
m/z = 385



0.90-1.50 (4H, m), 3.19 (1H, m),
(M + H)



5.07 (1H, d), 5.15 (1H, d), 6.09



(1H, t), 6.24 (1H, d), 7.11 (1H,



m), 7.27 (2H, m), 7.66 (1H, dd),



8.34 (1H, d)


1-662
0.75 (3H, d), 0.80 (3H, d), 0.94
m/z = 385



(3H, d), 1.61 (1H, m), 2.86 (1H,
(M + H)



m), 5.11 (2H, s), 6.09 (1H, t),



6.23 (1H, d), 7.11 (1H, t), 7.25



(1H, d), 7.30 (1H, d), 7.66 (1H,



dd), 8.34 (1H, d)


1-663
1.35 (3H, d), 4.33 (1H, q), 5.05
m/z = 419



(1H, d), 5.11 (1H, d), 6.00 (1H,
(M + H)



d), 6.08 (1H, t), 6.96 (1H, m),



7.15-7.26 (7H, m), 7.63 (1H,



dd), 8.33 (1H, d)


1-664
1.55-1.75 (3H, m), 1.95 (1H, m),
m/z = 445



2.70-2.88 (2H, m), 4.36 (1H, t),
(M + H)



5.05 (1H, d), 5.20 (1H, d), 6.13



(1H, t), 6.38 (1H, d), 6.96 (1H,



m), 7.02-7.20 (5H, m), 7.28 (1H,



d), 7.62 (1H, dd), 8.3 (1H, d)


1-665
1.57 (3H, d), 4.78 (1H, d), 4.91
m/z = 469



(1H, d), 5.18 (1H, q), 5.80 (1H,
(M + H)



d), 5.93 (1H, t), 6.72 (1H, m),



7.05 (1H, d), 7.14 (1H, d), 7.38



(3H, m), 7.54 (1H, dd), 7.62



(1H, d), 7.66 (1H, d), 7.80 (1H,



d), 7.84 (1H, d), 8.28 (1H, d)


1-666
0.74 (3H, t), 1.75 (2H, m), 4.03
m/z = 433



(1H, t), 5.06 (2H, dd), 5.85
(M + H)



(1H, d), 6.05 (1H, m), 6.86 (1H,



m), 7.10-7.28 (7H, m), 7.63 (1H,



dd), 8.33 (1H, d)


1-667
1.34 (3H, d), 4.45 (1H, q), 5.11
m/z = 409



(1H, d), 5.16 (1H, d), 6.07 (1H,
(M + H)



m), 6.14 (1H, td), 6.26 (2H, m),



7.11 (1H, m), 7.28 (3H, m), 7.67



(1H, dd), 8.36 (1H, d)


1-676
5.06 (2H, s), 5.37 (1H, s), 5.38
m/z = 481



(1H, d), 6.07 (1H, t), 6.85 (1H,
(M + H)



t), 7.10-7.28 (12H, m), 7.61



(1H, d), 8.33 (1H, s)


1-668
0.79 (9H, s), 0.85 (3H, d), 2.89
m/z = 399



(1H, q), 5.11 (2H, s), 6.08 (1H,
(M + H)



t), 6.23 (1H, d), 7.10 (1H, t),



7.23 (1H, d), 7.30 (1H, d), 7.65



(1H, d), 8.34 (1H, s)


















TABLE 54







MS or IR


Compound

(KBr, v,


No.
1H-NMR (CDCl3, δ, ppm)
cm−1)







47-2  
5.68 (2H, d), 6.57 (1H, m), 7.34
m/z = 334



(1H, d), 7.80 (1H, m), 7.97 (1H,
(M + H)



dd), 8.39 (1H, d), 8.57 (1H, s)


91-2  
5.92 (2H, s), 6.95 (1H, d), 7.30
m/z = 350



(1H, d), 7.69 (1H, m), 7.86 (1H,
(M + H)



dd), 8..49 (1H, dd), 8.53 (1H, d)


478-2  
2.59 (3H, s), 5.77 (2H, s), 6.75
m/z = 330



(1H, d), 7.31 (1H, d), 7.63 (1H,
(M + H)



dd), 7.72 (1H, m), 8.33 (1H, d),



8.45 (1H, d)


479-2  
2.73 (3H, s), 5.71 (2H, s), 6.73
m/z = 336



(1H, d), 7.63 (1H, s), 7.69 (1H,
(M + H)



t), 8.44 (1H, d)


1-51 
1.60 (2H, m), 1.73 (1H, m), 2.03
m/z = 369



(4H, m), 3.75 (1H, m), 5.12 (2H,
(M + H)



s), 6.12 (1H, t), 6.16 (1H, d),



7.10 (1H, m), 7.25 (1H, d), 7.32



(1H, d), 7.71 (1H, dd), 8.37



(1H, d)


566-2  
4.09 (3H, s), 5.71 (2H, s), 6.25
m/z = 346



(1H, d), 7.29 (1H, d), 7.74 (1H,
(M + H)



t), 7.97 (1H, dd), 8.17 (1H, d),



8.50 (1H, d)


488-2  
1.77 (1H, m), 2.11 (1H, m), 2.62
m/z = 289



(3H, s), 2.98 (1H, m), 3.53 (1H,
(M + H)



dd), 3.67 (1H, dd), 3.78 (1H,



m), 3.98 (1H, m), 4.22 (1H, m),



4.65 (1H, m), 6.73 (1H, d), 7.66



(1H, t), 8.32 (1H, d)


511-2  
5.58 (2H, s), 7.38 (1H, d), 7.86
m/z = 361



(1H, dd), 8.40 (1H, dd), 8.47
(M + H)



(1H, d), 8.55 (1H, d), 8.93 (1H, d)


1-669
1.42 (3H, d), 4.65 (1H, q), 5.12
m/z = 425



(2H, s), 6.13 (2H, m), 6.75 (1H,
(M + H)



d), 6.88 (1H, dd), 7.07 (1H, m),



7.11 (1H, d), 7.26 (2H, m), 7.65



(1H, dd), 8.35 (1H, d)


179-2  
5.30 (2H, s), 6.43 (1H, dd),
m/z = 332



6.66 (1H, dd), 7.40 (1H, d),
(M + H)



7.60 (2H, m), 8.20 (1H, d)


555-2  
3.87 (3H, s), 5.60 (2H, s), 7.51
m/z = 346



(1H, d), 7.88 (1H, dd), 7.93
(M + H)



(1H, dd), 8.34 (1H, d), 8.49



(1H, d), 8.56 (1H, d) (DMSO-d6)


577-2  
5.65 (2H, s), 6.87 (1H, td),
m/z = 349



7.30 (1H, d), 7.81 (1H, m), 8.08
(M + H)



(1H, dd), 8.13 (1H, d), 8.54



(1H, d)


544-2  
3.93 (3H, s), 5.45 (2H, s), 6.49
m/z = 346



(1H, dd), 7.31 (1H, d), 7.66
(M + H)



(1H, d), 7.83 (1H, dd), 8.13



(1H, d), 8.42 (1H, d)


168-2  
5.62 (2H, s), 7.43 (1H, d), 7.64
m/z = 332



(1H, dd), 7.88 (1H, dd), 7.94
(M + H)



(1H, d), 8.26 (1H, d), 8.49 (1H, d)


1-644
4.18 (2H, s), 4.68 (2H, s),
m/z = 368



5.36 (2H, s), 6.55 (1H, m),
(M + H)



7.16 (1H, d), 7.29 (1H, d),



7.35 (2H, m), 7.40 (2H, m),



1.52 (2H, m), 7.75 (1H, dd),



8.28 (1H, d), 8.40 (1H, d)


578-644 
4.19 (2H, s), 4.69 (2H, s),
m/z = 334



5.42 (2H, s), 6.52 (1H, m),
(M + H)



7.20 (1H, m), 7.30 (1H, m),



7.32 (2H, m), 7.40 (2H, m),



7.55 (2H, m), 7.72 (1H, dd),



8.30 (1H, dd), 8.52 (1H, dd),



8.62 (1H, d)


1-703
5.20 (1H, d), 5.45 (1H, d),
1715, 1636,



6.55 (1H, m) 7.34 (1H, m),
1552, 1505,



7.50 (1H, m), 7.60 (1H, m),
1457, 1174,



7.79 (1H, dd), 8.39 (1H, d)
1144


1-707
5.43 (2H, s), 6.93 (1H, m),
(EI-HRMS)



7.36 (1H, d), 7.77-7.85 (3H,
m/z = 351.0084



m), 7.95 (1H, dd), 8.39 (1H, d)
(M+)


1-706
1.20 (6H, m), 2.67 (4H, m),
m/z = 298



5.22 (2H, s), 6.52 (1H, m),.
(M + H)



7.31 (1H, m), 7.51 (1H, m),



7.60 (1H, dd), 7.73 (1H, m),



7.84 (1H, d), 8.41 (1H, d)


1-692
1.11 (3H, t), 1.20 (3H, t), 3.76
m/z = 356



(2H, m), 3.92 (2H, m), 6.58 (1H,
(M + H)



m), 7.26 (1H, d)., 7.53 (2H, m),



7.74 (1H, dd), 8.12 (1H, d), 8.40



(1H, d) (DMSO-d6)


1-700
1.20 (6H, m), 2.67 (4H, m), 5.22
m/z = 404



(2H, s), 6.52 (1H, m),. 7.31 (1H,
(M + H)



m), 7.51 (1H, m), 7.60 (1H, dd),



7.73 (1H, m), 7.84 (1H, d), 8.41



(1H, d)


1-701
0.95 (6H, m), 1.56 (4H, m), 2.62
m/z = 432



(4H, m), 5.18 (2H, s), 6.52 (1H,
(M + H)



m), 7.34 (1H, m), 7.49 (1H, m),



7.59 (1H, m), 7.77 (1H, dd), 7.84



(1H, d), 8.42 (1H, d)


1-702
1.13-1.46 (m, 12H), 3.20 (m, 2H),
m/z = 432



5.27 (s, 2H), 6.51 (m, 1H), 7.31
(M + H)



(m, 1H), 7.52 (m, 1H), 7.63 (m,



1H), 7.78 (m, 2H), 8.43 (d, 1H)


1-646
1.31 (6H, d), 4.95 (1H, sep),
1646, 1620,



5.40 (2H, s), 6.40 (1H, m), 7.28
1548, 1504,



(1H, d), 7.40 (2H, m), 7.73 (1H,
1453,



dd) 8.05 (1H, m), 8.40 (1H, d)


1-645
5.18 (2H, s), 5.37 (2H, s), 6.43
1655, 1518,



(1H, m), 7.25-7.36 (4H, m),
1455, 1399,



7.41-7.46 (4H, m), 7.72 (1H,
1235



dd), 8.12 (1H, m), 8.38 (1H, d)


1-643
5.52 (2H, s), 6.78 (1H, m), 7.31
1633, 1601,



(1H, d), 7.68-7.75 (3H, m), 8.39
1541, 1502,



(1H, m), 8.56 (1H, s)
1482, 1453,




1384


2-643
5.51 (2H, s), 6.80 (1H, m), 7.60
1632, 1597,



(1H, s), 7.75 (2H, m), 8.57 (1H, m)
1541, 1506,




1483, 1455,




1388









Further, the synthetic methods in the Table are described as follows.
A: the same method as in Synthetic Example 1
B: the same method as in Synthetic Example 2
C: the same method as in Synthetic Example 3
D: the same method as in Synthetic Example 4
E: the same method as in Synthetic Example 5
F: the same method as in Synthetic Example 6
G: the same method as in Synthetic Examples 7 and 8
H: the same method as in Synthetic Example 9
Preparation Example
Preparation Example 1 [Wettable Powder]
















Compound P212
10% by weight



Imidacloprid
20% by weight



Clay
50% by weight



White carbon
 2% by weight



Diatomaceous earth
13% by weight



Calcium ligninsulfonate
 4% by weight



Sodium lauryl sulfate
 1% by weight










The ingredients were homogeneously mixed and ground to obtain wettable powder.
Preparation Example 2 [Water Dispersible Granule]
















Compound P212
10% by weight



Imidacloprid
20% by weight



Clay
60% by weight



Dextrin
 5% by weight



Alkyl maleate copolymer
 4% by weight



Sodium lauryl sulfate
 1% by weight










The ingredients were homogeneously ground and mixed, water was added thereto to knead the ingredients thoroughly and then the mixture was granulated and dried to obtain water dispersible granules.
Preparation Example 3 [Flowables]














Compound 1-20
5%
by weight


Imidacloprid
20%
by weight


POE polystyrylphenyl ether sulfate
5%
by weight


Propylene glycol
6%
by weight


Bentonite
1%
by weight


1% xanthan-gum aqueous solution
3%
by weight


PRONALEX-300 (TOHO Chemical
0.05%
by weight


Industry Co., Ltd.)


ADDAC827 (KI Chemical Industry Co.,
0.02%
by weight


Ltd.)


Water
added to 100%
by weight









All the ingredients except for the 1% xanthan-gum aqueous solution and a suitable amount of water were premixed together from the blending, and the mixture was then ground by a wet grinder. Thereafter, the 1% xanthan-gum aqueous solution and the remaining water were added thereto to obtain 100% by weight of flowables.
Preparation Example 4 [Emulsifiable Concentrate]
















Compound P212
 2% by weight



Imidacloprid
13% by weight



N,N-dimethylformamide
20% by weight



Solvesso 150 (Exxon Mobil Corporation)
55% by weight



Polyoxyethylene alkyl aryl ether
10% by weight










The ingredients were homogeneously mixed and dissolved to obtain an emulsifiable concentrate.
Preparation Example 5 [Dust]
















Compound P212
0.5% by weight



Imidacloprid
1.5% by weight



Clay
 60% by weight



Talc
 37% by weight



Calcium stearate
  1% by weight










The ingredients were homogeneously mixed to obtain dust.
Preparation Example 6 [DL Dust]
















Compound P212
1% by weight



Tebufloquin
1% by weight



Ethofenprox
1% by weight



DL clay
94.5% by weight  



White carbon
2% by weight



Light liquid paraffin
0.5% by weight  










The ingredients were homogeneously mixed to obtain dust.
Preparation Example 7 [Microgranule Fine]
















Compound P212
1% by weight



Imidacloprid
1% by weight



Carrier
94% by weight 



White carbon
2% by weight



Hisol SAS-296
2% by weight










The ingredients were homogeneously mixed to obtain dust.
Preparation Example 8 [Granules]

















Compound 1-20
2%
by weight



Chlorantraniliprole
1%
by weight



Bentonite
39%
by weight



Talc
10%
by weight



Clay
46%
by weight



Calcium ligninsulfonate
2%
by weight










The ingredients were homogeneously ground and mixed, water was added thereto to knead the ingredients thoroughly, and then the mixture was granulated and dried to obtain granules.
Preparation Example 9 [Microcapsules]

















Compound 1-20
2%
by weight



Imidacloprid
3%
by weight



Urethane resin
25%
by weight



Emulsifier/Dispersant
5%
by weight



Antiseptic
0.2%
by weight



Water
64.8%
by weight










Microcapsules were obtained by forming a urethane resin coating on the surface of particles of the compound represented by Formula (I) and imidacloprid particles using the ingredients by interfacial polymerization.
Preparation Example 10 [Granules]
















Compound P212
2% by weight



Probenazole
24% by weight 



Sodium lauryl sulfate
1% by weight



Bentonite
2% by weight



Calcium stearate
1% by weight



PVA
2% by weight



Clay
68% by weight 










The ingredients were homogeneously ground and mixed, water was added thereto to knead the ingredients thoroughly, and then the mixture was granulated and dried to obtain granules.
Preparation Example 11 [Granules]

















Compound P212
2%
by weight



Chlorantraniliprole
1%
by weight



Probenazole
24%
by weight



Bentonite
40%
by weight



Talc
10%
by weight



Clay
21%
by weight



Calcium ligninsulfonate
2%
by weight










The ingredients were homogeneously ground and mixed, water was added thereto to knead the ingredients thoroughly, and then the mixture was granulated and dried to obtain granules.
Preparation Example 12 [Liquid Drops]

















Compound 1-20
10%
by weight



Fipronil
1%
by weight



Benzyl alcohol
73.9%
by weight



Propylene carbonate
15%
by weight



BHT
0.1%
by weight










The ingredients were homogeneously stirred and dissolved to obtain liquid drops.
Preparation Example 13 [Liquid Drops]
















Compound P212
48% by weight



Fipronil
 2% by weight



Ethanol
50% by weight










The ingredients were homogeneously mixed to obtain liquid drops.
Preparation Example 14 [Emulsifiable Concentrate]
















Compound 1-20
 5% by weight



Etoxazole
 5% by weight



Xylene
35% by weight



Dimethyl sulfoxide
35% by weight










The ingredients were dissolved, and 14% by weight of polyoxyethylene styryl phenyl ether and 6% calcium dodecylbenzenesulfonate were added thereto, and the mixture was thoroughly stirred and mixed to obtain a 10% emulsifiable concentrate.
Preparation Example 15 [Liquid Drops]
















Compound P212
10% by weight



Etoxazole
 5% by weight



Glycol (glycol mono alkyl ether)
85% by weight



BHT or BHA
appropriate amount










An appropriate amount of sorbitan monooleate or sorbitan monolaurate, caprylic acid monoglyceride or isostearic acid monoglyceride, or propylene glycol monocaprylate was added to the ingredients, and alcohol or propylene carbonate, N-methyl-2-pyrrolidone or water was added thereto to obtain liquid drops as 100% by weight.
Reference Test Example
<Foliar Treatment Test of Single Agent>
Reference Test Example 1 Pest Control Test of Plutella xylostella 
A leaf disk having a diameter of 5.0 cm was cut out from a cabbage in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.
Reference Test Example 2 Pest Control Test of Spodoptera litura 
A leaf disk having a diameter of 5.0 cm was cut out from a cabbage in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, third instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 500 ppm.
Reference Test Example 3 Pest Control Test of Aphis gossypii 
A leaf disk having a diameter of 2.0 cm was cut out from a cucumber in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, first instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.
Reference Test Example 4 Pest Control Test of Laodelphax striatella 
A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.
Reference Test Example 5 Pest Control Test of Nilaparvata lugens 
A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Six days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.
Reference Test Example 6 Pest Control Test of Sogatella furcifera 
A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Four days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.
Reference Test Example 7 Pest Control Test of Nephotettix cincticeps 
A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Four days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compound P212 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.
Reference Test Example 8 Pest Control Test of Trialeurodes vaporariorum 
Adult greenhouse whiteflies were released to a cucumber in pot culture and allowed to lay eggs overnight. One day after the onset of egg laying, the adults were removed and the eggs were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the completion of egg laying, a leaf disk having a diameter of 2.0 cm was cut out from the cucumber, it was confirmed that the eggs had been laid, and then a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After the spraying, the leaf disk was left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Fourteen days after the spraying, larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={(number of eggs laid −number of survived larvae)/number of eggs laid)}×100

As a result, compound P212 exhibited high insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 9 Pest Control Test of Frankliniella occidentalis 
A leaf disk having a diameter of 2.8 cm was cut out from a kidney bean in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, first instar larvae were released to the leaf disk. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidal activity having a mortality of 80% or higher by a foliage treatment at 500 ppm.
Reference Test Example 10 Pest Control Test of Trigonotylus caelestialium 
Wheat seedling leaves and stems four days after the dissemination of seedlings were dipped for 30 seconds in a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available). After an air drying process, the wheat seedling leaves and stems were placed into a glass tube, and two second instar larvae of Trigonotylus coelestialium were released to the same glass tube. After the larvae were released, the tube was lidded to leave the larvae to stand in a thermostatic chamber at 25° C. In order to supply water to the wheat during the test, water was given to the wheat from the bottom of the glass tube. Three days after the treatment, the larvae were observed for survival or death, and the death rate of larvae was calculated by the following equation. Test in triplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a dipping treatment of the drug solution at 50 ppm.
Reference Test Example 11 Pest Control Test of Plautia crossota stali 
A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to a young fruit of apple collected outdoors. After an air drying process, the young fruit was placed into a plastic cup, and two adults of Plautia crossota stall were released thereto. Six days after the release, the adults were observed for survival or death, the Mortality of adults was calculated by the following equation.

Mortality of adults (%)={number of dead adults/(number of survived adults+number of dead adults)}×100

As a result, compound P212 exhibited insecticidal activity having a mortality of 60% or higher by a foliar treatment at 50 ppm.
Reference Test Example 12 Pest Control Test of Oulema oryzae 
1 μL (/head) of a drug solution of the compound of Formula (I) prepared at a predetermined concentration with acetone was topically applied and treated to the back of adults collected outdoors by a micro syringe. After the drug treatment, the adults were transferred to rice seedlings and left to stand in a thermostatic chamber at 25° C. so as to obtain 5 heads per stem. Forty eight hours after the treatment, the adults were observed for survival or death, and the mortality of adults was calculated by the following equation. Test in duplicate.

Mortality of adults (%)={number of dead adults/(number of survived adults+number of dead adults)}×100

As a result, compound P212 exhibited high insecticidal activity having a mortality of 80% or higher in a throughput of 0.5 μg/head.
Reference Test Example 13 Pest Control Test of Musca domestica 
The backs of female adults raised indoors were treated with 1 μL (/head) of a drug solution of the compound of Formula (I) prepared at a predetermined concentration with acetone. After the drug treatment, the adults were transferred to a plastic cup and left to stand in a thermostatic chamber at 25° C. so as to obtain 5 heads per cup. Twenty four hours after the treatment, the agony situation of the adults was observed, and the rate of agonized adults was calculated by the following equation. Test in duplicate.

Mortality of adults (%)={number of dead adults/(number of survived adults+dead adults)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidal activity having a mortality of 80% or higher in a throughput of 2 μg/head.
<Soil Drench Test of Single Agent>
Reference Test Example 14 Pest Control Test of Laodelphax striatella 
A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second instar larvae of Laodelphax striatella were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidal activity having a mortality of 80% or higher in a throughput of 0.05 mg/seedling.
Reference Test Example 15 Pest Control Test of Sogatella furcifera 
A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second instar larvae of Sogatella furcifera were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidal activity having a mortality of 80% or higher in a throughput of 0.05 mg/seedling.
Reference Test Example 16 Pest Control Test of Nilaparvata lugens 
A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I), which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second instar larvae of Nilaparvata lugens were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidal activity having a death rate of 80% or higher in a throughput of 0.05 mg/seedling.
Reference Test Example 17 Pest Control Test of Lissorhoptrus oryzophilus 
A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I), which had been prepared so as to be a 10% acetone water. Two days after the treatment, five adults of Lissorhoptrus oryzophilus were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compound P212 exhibited high insecticidal activity having a mortality of 80% or higher in a throughput of 0.1 mg/seedling.
Reference Test Example 18 Pest Control Test of Laodelphax striatella 
Wheat seedling roots forty eight hours after the dissemination of seeds were treated with a drug solution of the compound of the present invention at a predetermined concentration, which had been prepared so as to be a 10% acetone water. The drug was absorbed from the roots for 72 hours, and then ten second instar larvae of Laodelphax striatella were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Four days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-204 exhibited insecticidal activity having a mortality of 80% or higher in a throughput of 20 kg/seedling.
The results of Reference Test Examples 1, 3 and 18 are shown in the following Table.













TABLE 55









Plutella

Laodelphax






xylostella
Aphisgossypii
striatella


Reference



(Reference
(Reference
(Reference


Example



Test
Test
Test


Compound



Example
Example
Example


No.
Ar
Y
R
1)
3)
18)





















P-212
6-chloro-
H
COCF3
100
100
100



3-pyridyl


P-213
2-chloro-
H
COCF3
100
100
100



5-



thiazolyl


P-215
6-chloro-
5-
COCF3
100
80
75



3-pyridyl
Cl


P-216
6-chloro-
5-F
COCF3
100
95
100



3-pyridyl


P-218
2-chloro-
5-
COCF3
100
60



5-
Cl



thiazolyl


P-219
2-chloro-
5-F
COCF3
80
85



5-



thiazolyl


P-222
6-chloro-
4-
COCF3

100
100



3-pyridyl
Me


P-223
6-chloro-
5-
COCF3

75
75



3-pyridyl
Me


P-225
4-chloro-
H
COCF3

90



phenyl


P-226
3-pyridyl
H
COCF3
60
100


P-227
6-chloro-
H
COCF3
100
100
100



5-fluoro-



3-pyridyl


P-228
6-
H
COCF3
30
95
100



trifluoromethyl-



3-



pyridyl


P-229
6-fluoro-
H
COCF3
100
100
100



3-pyridyl


P-230
5,6-
H
COCF3
100
100



dichloro-



3-pyridyl


P-231
6-bromo-3-
H
COCF3
100
100
100



pyridyl


P-232
6-chloro-
4-F
COCF3

80



3-pyridyl


P-233
6-chloro-
3-F
COCF3

100
75



3-pyridyl


P-234
6-chloro-
H
COCHCl2
100
100
100



3-pyridyl


P-235
6-chloro-
H
COCCl3
100
95
75



3-pyridyl


P-236
6-chloro-
H
COCH2Cl

100



3-pyridyl


P-238
6-chloro-
H
COCHF2
100
100
100



3-pyridyl


P-239
6-chloro-
H
COCF2Cl
100
100
100



3-pyridyI


P-240
6-chloro-
H
COCHClBr

100
100



3-pyridyl


P-241
6-chloro-
H
COCHBr2

100
100



3-pyridyl


P-242
6-chloro-
H
COCF2CF3
100
100
100



3-pyridyl


P-243
2-chloro-
H
COCF3
100
100
100



5-



pyrimidinyl


P-244
6-chloro-
H
COCH2Br

100
100



3-pyridyl


1-20
6-chloro-
H
CSCF3
100
100
100



3-pyridyl


1-21
6-chloro-
H
CSCHF2
80
100
100



3-pyridyl


1-22
6-chloro-
H
CSCF2Cl
100

100



3-pyridyl


1-23
6-chloro-
H
CSCF2CF3
100

100



3-pyridyl


1-42
6-chloro-
H
C(═NOMe)CF3
100
100
100



3-pyridyl


1-150
6-chloro-
H
C(═NCH2CH2SMe)CF3
100
100
80



3-pyridyl


3-3
6-fluoro-
H
COCHF2
50
100
80



3-pyridyl


3-4
6-fluoro-
H
COCF2Cl
100
100
100



3-pyridyl


3-5
6-fluoro-
H
COCF2CF3
100
55
80



3-pyridyl


3-20
6-fluoro-
H
CSCF3
55
100
80



3-pyridyl


4-3
6-Bromo-3-
H
COCHF2
100

100



pyridyl


4-4
6-Bromo-3-
H
COCF2Cl
100

100



pyridyl


4-5
6-Bromo-3-
H
COCF2CF3
100
100
100



pyridyl


4-20
6-Bromo-3-
H
CSCF3
100
100
100



pyridyl


5-3
6Chloro-
H
COCHF2
100

100



5fluoro-



3pyridyl


5-4
6Chloro-
H
COCF2Cl
100

100



5fluoro-



3pyridyl


5-20
6Chloro-
H
CSCF3
100

100



5fluoro-



3pyridyl


6-3
2-Cl-5-
H
COCHF2
80

100



pyrimidinyl


6-4
2-Cl-5-
H
COCF3Cl
90
100
100



pyrimidinyl


102-2
6-chloro-
3-
COCF3
10
100
100



3-pyridyl
CN









<Effects Against Insecticide Resistant Pests>
Reference Test Example 19 Pest Control Test of Nilaparvata lugens 
A rice seedling in pot culture was subjected to soil drench with a solution of the compound of Formula (I), which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second instar larvae of Nilaparvata lugens, which had been collected outdoors and proliferated indoors, were each released to the rice seedling. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Six days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, for comparison, the test against a species of Nilaparvata lugens which is highly susceptible to imidacloprid was performed by the same method as described above, and the results thereof are shown in Table 45. As described in Table 45, Compound P212 and Compound 1-20 exhibited high insecticidal effects against susceptible species and drug resistant species of Nilaparvata lugens, and the death rates of larvae at 0.005 mg/seedling were (susceptible species) 100% and 100%, (resistant population I) 95% and 77% and (resistant population II) 100% and 85%, respectively. Meanwhile, the death rates of imidacloprid at 0.05 mg/seedling were (susceptible species) 100%, (resistant population I) 38% and (resistant population II) 69%, and the insecticidal effect thereof was also low even at a high dose. From the above results, it became obvious that Compound P212 and Compound 1-20 have high insecticidal effects even against Nilaparvata lugens resistance against imidacloprid.
Further, for the origin of test pests, bugs collected outdoors from the Kumamoto prefecture (I) in 2007 and from the Fukuoka prefecture (II) in 2005 as resistant population of Nilaparvata lugens, and bugs collected from the Kagoshima prefecture and then successively reared indoors for a long time as the imidacloprid susceptible population of Nilaparvata lugens were used.







TABLE 56







Insecticidal effects against Nilaparvata lugens (death rate %)









Effects against Nilaparvata lugens













Susceptible
Resistant
Resistant




population
population I
population II




six days
six days
six days



Throughput
after the
after the
after the



(mg/seedling)
treatment
treatment
treatment















P212
0.05
100
100
100



0.005
100
95
100


1-20
0.01
95
100
100



0.005
100
77
85


Imidacloprid
0.05
100
38
69



0.01
100

39









<Mixed Agent Test Example>
Test Example 1 Soil Irrigation Treatment Test of Laodelphax striatella 
A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 10% acetone water. After the rice seedling was left to stand for 3 days, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

In addition, when there was no synergistic effect, a theoretical value was calculated by the Colby's equation shown as follows, and the results are shown in the Table.

theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212 or Compound 1-20)
B: 100−(mortality of larvae or adults when treated only with each of imidacloprid, fipronil, chlorantraniliprole, spinosad, clothianidin, dinotefuran, sulfoxaflor, pymetrozine, thiamethoxam, flupyradifurone and cycloxaprid))
Method for Judging Synergistic Effects
When the mortality against Laodelphax striatella in the case of a mixture with another agent exceeded the theoretical value by the Colby's equation, a synergistic effect was judged to be present.
It was demonstrated that mixed agents of the insecticides of imidacloprid, fipronil, chlorantraniliprole, spinosad, clothianidin, dinotefuran, sulfoxaflor, pymetrozine, thiamethoxam, flupyradifurone and cycoxaprid, which were provided and tested as Compound P212, all show a mortality of larvae or adults, exceed the theoretical value and have synergistic effects.
In addition, it was demonstrated that mixed agents of the insecticides of imidacloprid and fipronil, which were provided and tested as Compound 1-20, all show a mortality of larvae or adults, exceed the theoretical value and have synergistic effects.
Furthermore, it was demonstrated that mixed agents of the fungicides of probenazole, isotianil, tiadinil and orysastrobin, which were provided and tested as Compound P212, all exhibit insecticidal effect equal to or higher than the insecticidal effect when treated with Compound P212 alone and may be mixed and treated with a fungicide. Likewise, it was demonstrated that mixed agents of the fungicide of probenazole, which was provided and tested as Compound 1-20, exhibit insecticidal effect equal to or higher than the insecticidal effect when treated with Compound 1-20 alone and may be mixed and treated with a fungicide.
<Example of Mixed Agent with Insecticide>







TABLE 57







Mortality (%) of single agent and mixed


agent against Laodelphax striatella











Rate
Compound P212













Insecticide name
mg/Seedling
0
0.005
















—
—
0
39



Imidacloprid
0.005
0
70



Fipronil
0.005
26
65



Chlorantraniliprole
0.05
9
60



Spinosad
0.5
0
62

















TABLE 58







Theoretical value (%) by Colby's equation











Rate
Compound P212













Insecticide name
mg/Seedling
0
0.005
















—
—
0
39



Imidacloprid
0.005
0
39



Fipronil
0.005
26
55



Chlorantraniliprole
0.05
9
44



Spinosad
0.5
0
39

















TABLE 59







Mortality (%) of single agent and mixed


agent against Laodelphax striatella











Rate
Compound P212













Insecticide name
mg/Seedling
0
0.005
















—
—
0
18



Clothianidin
0.005
23
56



Dinotefuran
0.005
0
30



Sulfoxaflor
0.005
1
63



Pymetrozine
0.05
15
89

















TABLE 60







Theoretical value (%) by Colby's equation











Rate
Compound P212













Insecticide name
mg/Seedling
0
0.005
















—
—
0
18



Clothianidin
0.005
23
37



Dinotefuran
0.005
0
18



Sulfoxaflor
0.005
1
19



Pymetrozine
0.05
15
30

















TABLE 61







Mortality (%) of single agent and mixed


agent against Laodelphax striatella











Rate
Compound P212













Insecticide name
mg/Seedling
0
0.005
















—
—
0
14



Thiamethoxam
0.01
23
45

















TABLE 62







Theoretical value (%) by Colby's equation











Rate
Compound P212













Insecticide name
mg/Seedling
0
0.005
















—
—
0
14



Thiamethoxam
0.01
23
34

















TABLE 63







Mortality (%) of single agent and mixed


agent against Laodelphax striatella











Rate
Compound P212













Insecticide name
mg/Seedling
0
0.005







—
—
0
45



Flupyradifurone
0.01
5
85

















TABLE 64







Theoretical value (%) by Colby's equation











Rate
Compound P212













Insecticide name
mg/Seedling
0
0.005







—
—
0
45



Flupyradifurone
0.01
5
48

















TABLE 65







Mortality (%) of single agent and mixed


agent against Laodelphax striatella











Rate
Compound 1-20













Insecticide name
mg/Seedling
0
0.005







—
—
0
12



Imidacloprid
0.005
0
74



Fipronil
0.001
0
80

















TABLE 66







Theoretical value (%) by Colby's equation











Rate
Compound 1-20













Insecticide name
mg/Seedling
0
0.005







—
—
0
12



Imidacloprid
0.005
0
12



Fipronil
0.001
0
12

















TABLE 67







Mortality (%) of single agent and mixed


agent against Laodelphax striatella











Rate
Compound P212













Insecticide name
mg/Seedling
0
0.005







—
—
0
0



Cycloxaprid
0.005
0
7

















TABLE 68







Theoretical value (%) by Colby's equation











Rate
Compound P212













Insecticide name
mg/Seedling
0
0.005







—
—
0
0



Cycloxaprid
0.005
0
0

















TABLE 69







Mortality (%) of single agent and mixed


agent against Laodelphax striatella











Rate
Compound P212
Compound 1-20












Fungicide name
mg/Seedling
0
0.005
0
0.005















—
—
0
39
0
8


Probenazole
0.5
9
59
9
65
















TABLE 70







Theoretical value (%) by Colby's equation











Rate
Compound P212
Compound 1-20












Fungicide name
mg/Seedling
0
0.005
0
0.005















—
—
0
39
0
8


Probenazole
0.5
9
44
9
16
















TABLE 71







Mortality (%) of single agent and mixed


agent against Laodelphax striatella











Rate
Compound P212













Fungicide name
mg/Seedling
0
0.005







—
—
0
19



Isotianil
0.5
5
30



Tiadinil
0.5
8
30



Orysastrobin
0.5
4
70

















TABLE 72







Theoretical value (%) by Colby's equation











Rate
Compound P212













Fungicide name
mg/Seedling
0
0.005







—
—
0
19



Isotianil
0.5
5
23



Tiadinil
0.5
8
25



Orysastrobin
0.5
4
22










Test Example 2 Foliar Treatment Test Against Laodelphax striatella 
A drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Further, when there was no synergistic effect, a theoretical value was calculated by the Colby's equation shown as follows, and the results are shown in the Table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212 or Compound 1-20)
B: 100−(mortality of larvae or adults when treated only with etofenprox or silafluofen))
Method for Judging Synergistic Effects
When the mortality against Laodelphax striatella in the case of a mixture with another agent exceeded the theoretical value by the Colby's equation, a synergistic effect was judged to be present.
It was demonstrated that mixed agents of the insecticides of etofenprox and silafluofen, which were provided and tested as Compound P212 or Compound 1-20, all show a mortality of larvae or adults approximately equal to the theoretical value, and may be mixed with the insecticide even in a foliar treatment-like usage.







TABLE 73







Mortality (%) of single agent and mixed agent


against Laodelphax s striatella
















Compound
Compound



Insecticide
Rate
—
P212
1-20



name
(ppm)
0
0.625
0.625

















—

0
95
90



Etofenprox
10
30
90
95



Silafluofen
5
55
100
100

















TABLE 74







Theoretical value (%) by Colby's equation
















Compound
Compound



Insecticide
Rate
—
P212
1-20



name
(ppm)
0
0.625
0.625

















—

0
95
90



Etofenprox
10
30
97
93



Silafluofen
5
55
98
95










Test Example 3 Pest Control Test of Aphis gossypii 
A leaf disk having a diameter of 2.0 cm was cut out from a cucumber in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, first instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

In addition, when there was no synergistic effect, a theoretical value was calculated by the Colby's equation shown as follows, and the results are shown in the Table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212 or Compound 1-20)
B: 100−(mortality of larvae or adults when treated only with afidopyropen)
Method for Judging Synergistic Effects
When the mortality against Aphis gossypii in the case of a mixture with another agent exceeded the theoretical value by the Colby's equation, a synergistic effect was judged to be present.
It was demonstrated that mixed agents of compounds of Formula (II), which were provided and tested as Compound P212 or Compound 1-20, all show a mortality of larvae or adults, exceed the theoretical value and have synergistic effects.







TABLE 75







Mortality (%) of single agent and mixed


agent against Aphis gossypii










Insecticide
Rate
Compound P212
Compound 1-20












name
ppm
0
0.313
0
0.625















—
—
0
45
0
19


Afidopyropen
0.002
25
70
25
40
















TABLE 76







Theoretical value (%) by Colby's equation










Insecticide
Rate
Compound P212
Compound 1-20












name
ppm
0
0.313
0
0.625















—
—
0
45
0
19


Afidopyropen
0.002
25
59
25
39









Test Example 4 Pest Control Test of Plutella xylostella 
A leaf disk having a diameter of 5.0 cm was cut out from a cabbage in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, when there was no synergistic effect, a theoretical value was calculated by the Colby's equation shown as follows, and the results are shown in the Table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated with only Compound P212)
B: 100−(mortality of larvae or adults when treated with only flometoquin, spinosad, fipronil, chlorantraniliprole, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, or afidopyropen))
Method for Judging Synergistic Effects
When the mortality against Plutella xylostella in the case of a mixture with another agent exceeded the theoretical value by the Colby's equation, a synergistic effect was judged to be present.
It was demonstrated that a mixed agent of the insecticide of flometoquin, which was provided and tested, with Compound P212, shows a death rate of larvae or adults, exceeds the theoretical value and has synergistic effects.







TABLE 77







Mortality (%) of single agent and mixed agent against


Plutella xylostella











Rate
Compound P212













Insecticide name
ppm
0
1.25
















—
—
0
0



Flometoquin
0.313
0
30

















TABLE 78







Theoretical value (%) by Colby's equation












Insecticide
Rate
Compound P212













name
ppm
0
1.25







—
—
0
0



Flometoquin
0.313
0
0

















TABLE 79







Mortality (%) of single agent and mixed agent


against Plutella xylostella










Compound P212




Rate ppm












Insecticide name

0
1.0
















—

0
40













Afidopyropen
Rate
10
20
70



Spinosad
ppm
0.01
11
70

















TABLE 80







Theoretical value (%) by Colby's equation










Compound P212




Rate ppm












Insecticide name

0
1.0
















—

0
40













Afidopyropen
Rate
10
20
52



Spinosad
ppm
0.01
11
45

















TABLE 81







Mortality (%) of single agent and mixed agent


against Plutella xylostella










Compound P212




Rate ppm












Insecticide name

0
1.0







—

0
30













Afidopyropen
Rate
5
0
80




ppm

















TABLE 82







Theoretical value (%) by Colby's equation










Compound P212




Rate ppm












Insecticide name

0
1.0







—

0
30













Afidopyropen
Rate
5
0
30




ppm

















TABLE 83







Mortality (%) of single agent and mixed agent


against Plutella xylostella










Compound P212




Rate ppm












Insecticide name

0
2.0
















—

0
60













Fipronil
Rate
0.04
50
100



Chlorantraniliprole
ppm
0.002
60
100

















TABLE 84







Theoretical value (%) by Colby's equation










Compound P212




Rate ppm












Insecticide name

0
2.0
















—

0
60













Fipronil
Rate
0.04
50
80



Chlorantraniliprole
ppm
0.002
60
84

















TABLE 85







Mortality (%) of single agent and mixed agent


against Plutella xylostella










Compound P212




Rate ppm












Insecticide name

0
2.0
















—

0
50













1-((6-
Rate
1
30
70



chloropyridin-
ppm



3-yl)methyl)-4-



oxo-3-phenyl-



4H-pyrido[1,2-



a]pyrimidin-1-



ium-2-olate



Afidopyropen

5
0
100

















TABLE 86







Theoretical value (%) by Colby's equation










Compound P212




Rate ppm












Insecticide name

0
2.0
















—

0
50













1-((6-
Rate
1
30
65



chloropyridin-
ppm



3-yl)methyl)-4-



oxo-3-phenyl-



4H-pyrido[1,2-



a]pyrimidin-1-



ium-2-olate



Afidopyropen

5
0
50










Test Example 5 Pest Control Test of Spodoptera litura 
A leaf disk having a diameter of 5.0 cm was cut out from a cabbage in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, third instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby's equation given below, and the results are shown in the tables.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212)
B: 100−(mortality of larvae or adults when treated with only the insecticide chlorantraniliprole, emamectin benzoate, flometoquin, or afidopyropen))
Method for Judging Synergistic Effects
When the mortality against Spodoptera litura in the case of a mixture with another agent exceeded the theoretical value given by Colby's equation, a synergistic effect was judged to be present.
It was demonstrated that a mixed agent of the insecticide chlorantraniliprole, emamectin benzoate, flometoquin, or afidopyropen tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value and has synergistic effects.







TABLE 87







Mortality (%) of single agent and mixed agent


against Spodoptera litura (1)










Compound P212




Rate ppm












Insecticide name

0
20







—

0
40













Afidopyropen
Rate
10
0
80




ppm

















TABLE 88







Theoretical value (%) by Colby's equation










Compound P212




Rate ppm












Insecticide name

0
20







—

0
40













Afidopyropen
Rate
10
0
40




ppm

















TABLE 89







Mortality (%) of single agent and mixed agent


against Spodoptera litura (2)










Compound P212




Rate ppm












Insecticide name

0
20
















—

0
10













Chlorantraniliprole
Rate
0.02
20
30



Emamectin benzoate
ppm
0.02
0
20

















TABLE 90







Theoretical value (%) by Colby's equation










Compound P212




Rate ppm












Insecticide name

0
20
















—

0
10













Chlorantraniliprole
Rate
0.02
20
28



Emamectin benzoate
ppm
0.02
0
10

















TABLE 91







Mortality (%) of single agent and mixed agent


against Spodoptera litura (3)










Compound P212




Rate ppm












Insecticide name

0
50
















—

0
10













Flometoquin
Rate
5
10
20



Afidopyropen
ppm
5
0
50

















TABLE 92







Theoretical value (%) by Colby's equation










Compound




P212



Rate



ppm











Insecticide name
0
50















—
0
10













Flometoquin
Rate
5
10
19



Afidopyropen
ppm
5
0
10










Test Example 6 Pest Control Test of Frankliniella occidentalis 
A leaf disk having a diameter of 2.8 cm was cut out from the common bean in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, first instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby's equation given below, and the results are shown in the table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212)
B: 100−(mortality of larvae or adults when treated with only the insecticide imidacloprid, dinotefuran, or acetamiprid))
Method for Judging Synergistic Effects
When the mortality against Frankliniella occidentalis in the case of a mixture with another agent exceeded the theoretical value given by Colby's equation, a synergistic effect was judged to be present.
It was demonstrated that a mixed agent of the insecticide imidacloprid or dinotefuran tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value and has synergistic effects.







TABLE 93







Mortality (%) of single agent and mixed agent


against Frankliniella occidentalis (1)










Compound




P212



Rate



ppm











Insecticide name
0
10















—
0
69













Imidacloprid
Rate
20
69
94




ppm

















TABLE 94







Theoretical value (%) by Colby's equation










Compound




P212



Rate



ppm











Insecticide name
0
10















—
0
69













Imidacloprid
Rate
20
69
90




ppm

















TABLE 95







Mortality (%) of single agent and mixed agent


against Frankliniella occidentalis (2)










Compound




P212



Rate



ppm











Insecticide name
0
20















—
0
70













Dinotefuran
Rate
5
35
85




ppm

















TABLE 96







Theoretical value (%) by Colby's equation










Compound




P212



Rate



ppm











Insecticide name
0
20















—
0
70













Dinotefuran
Rate
5
35
81




ppm










Test Example 7 Soil Irrigation Treatment Test on Chilo suppressalis 
Rice seedlings in pot culture were submitted to a soil irrigation treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 10% acetone water. After standing for 3 days, second instar larvae were released thereto. This was followed by standing in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Six days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby's equation given below, and the results are shown in the table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212)
B: 100−(mortality of larvae or adults when treated with only the insecticide fipronil, cyantraniliprole or spinosad))
Method for Judging Synergistic Effects
When the insecticidal effect (table) against Chilo suppressalis in the case of a mixture with another agent exceeded the theoretical value given by Colby's equation, a synergistic effect was judged to be present.
It was demonstrated that a mixed agent of the insecticide fipronil, cyantraniliprole or spinosad tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value in both cases and has synergistic effects.







TABLE 97







Mortality (%) of single agent and mixed agent


against Chilo suppressalis (1)










Compound




P212



Rate



mg/seedling











Insecticide name
0
0.01















—
0
33













Cyantraniliprole
Rate
0.005
83
100




mg/seedling

















TABLE 98







Theoretical value (%) by Colby's equation










Compound




P212



Rate



mg/seedling











Insecticide name
0
0.01















—
0
33













Cyantraniliprole
Rate
0.005
83
89




mg/seedling

















TABLE 99







Mortality (%) of single agent and mixed agent


against Chilo suppressalis (2)










Compound




P212



Rate



mg/seedling











Insecticide name
0
0.002















—
0
40













Fipronil
Rate
0.0005
40
80



Chlorantraniliprole
mg/seedling
0.0005
60
80



Spinosad

0.002
80
100

















TABLE 100







Theoretical value (%) by Colby's equation










Compound




P212



Rate



mg/seedling











Insecticide name
0
0.002















—
0
40













Fipronil
Rate
0.0005
40
64



Chlorantraniliprole
mg/seedling
0.0005
60
76



Spinosad

0.002
80
88










Test Example 8 Soil Irrigation Treatment Test on Naranga aenescens 
Rice seedlings in pot culture were subjected to a soil irrigation treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 10% acetone water. After standing for 3 days, first instar larvae were released thereto. This was followed by standing in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Five days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby's equation given below, and the results are shown in the table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212)
B: 100−(mortality of larvae or adults when treated with only the insecticide spinosad or fipronil))
Method for Judging Synergistic Effects
When the mortality against Naranga aenescens in the case of a mixture with another agent exceeded the theoretical value given by Colby's equation, a synergistic effect was judged to be present.
It was demonstrated that a mixed agent of the insecticide spinosad or fipronil tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value in all cases and has synergistic effects.







TABLE 101







Mortality (%) of single agent and mixed agent


against Naranga aenescens










Compound




P212



Rate



mg/seedling











Insecticide name
0
0.01















—
0
60













Spinosad
Rate
0.005
40
100



Fipronil
mg/seedling
0.01
20
80

















TABLE 102







Theoretical value (%) by Colby's equation










Compound




P212



Rate



mg/seedling











Insecticide name
0
0.01















—
0
60













Spinosad
Rate
0.005
40
76



Fipronil
mg/seedling
0.01
20
68










Test Example 9 Test on Callosobruchus chinensis 
A compound of Formula (I) and the insecticide indicated below, prepared in predetermined concentrations using acetone, were separately topically applied to the back of the same adult Callosobruchus chinensis. The Callosobruchus chinensis was then introduced into a plastic cup and held in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. One day after the release, the insects were observed for survival or death, and the insect mortality was calculated by the following equation. The test was performed in duplicate.

Insect mortality (%)={number of dead insects/(number of survived insects+number of dead insects)}×100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby's equation given below, and the results are shown in the table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(insect mortality for treatment with only Compound P212)
B: 100−(insect mortality for treatment with only the insecticide fipronil or imidacloprid))
Method for Judging Synergistic Effects
When the mortality against Callosobruchus chinensis in the case of a mixture with another agent exceeded the theoretical value given by Colby's equation, a synergistic effect was judged to be present.
It was demonstrated that co-treatment with the insecticide fipronil or imidacloprid tested with Compound P212 shows an insect mortality in excess of the theoretical value in both cases and has synergistic effects.







TABLE 103







Mortality (%) of single agent and mixed agent


against Callosobruchus chinensis










Compound




P212



Rate



ng/head











Insecticide name
0
0.2















—
0
20













Fipronil
Rate
0.2
0
36



Imidacloprid
ng/head
0.2
40
60

















TABLE 104







Theoretical value (%) by Colby's equation










Compound




P212



Rate



ng/head











Insecticide name
0
0.2















—
0
20













Fipronil
Rate
0.2
0
20



Imidacloprid
ng/head
0.2
40
52










Test Example 10 Pest Control Test of Rice Blast
A rice seedling in pot culture was subjected to soil irrigation treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared with a 10% acetone water. Three days after the treatment, a spore suspension (2×105 ea/mL, 0.05% Tween available) of rice blast bacteria was sprayed and inoculated thereto, and the rice seedling was placed in a moist chamber for 24 hours to promote infection. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Seven days after the inoculation, the number of lesions was measured, and the preventive value was calculated by the following equation. The test was performed in triplicate.

Preventive value={(number of lesions in a zone without treatment−number of lesions in a zone with treatment)/(number of lesions without treatment)}×100

As a result, it was demonstrated that in a throughput of probenazole at 0.125 mg/seedling, any one mixed agent of Compound P212 and Compound 1-20 exhibits insecticidal effect equal to the insecticidal effect when treated with probenazole alone and may be mixed and treated with a fungicide.










TABLE 105









Compound
Compound



P212
1-20









Rate



mg/seedling











Insecticide name
0
2.5
0
2.5














—
0
3.3
0
52.5













Probenazole
Rate
0.125
96.7
93.4
96. 7
91.8



mg/seedling









Test Example 11 Test of Rice Blast Control (Foliar Treatment)
Rice seedlings were treated by foliar application with a drug solution of the compound of Formula (I), or a drug solution of a mixture of a compound of Formula (I) and the fungicide indicated below, prepared in a predetermined concentration with 10% acetone water. After the treatment, a rice blast spore suspension (1.5×105 ea/mL, 0.05% Tween available) was sprayed and inoculated thereto followed by holding in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Fourteen days after the inoculation, the number of lesions was measured, and the preventive value was calculated by the following equation. The test was performed in triplicate.

Preventive value={(number of lesions in a zone without treatment−number of lesions in a zone with treatment)/(number of lesions in a zone without treatment)}×100

As a result, it was demonstrated that at a treatment concentration of 0.5 ppm using tiadinil, isotianil, orysastrobin, tricyclazole, diclocymet, tebufloquin, azoxystrobin or kasugamycin, the mixed agent with Compound P212 also exhibits a fungicidal effect equal to that for treatment with tiadinil, isotianil, orysastrobin, tricyclazole, diclocymet, tebufloquin, azoxystrobin or kasugamycin alone and a mixed treatment with a fungicide is therefore possible.







TABLE 106







(Rice blast test 1)










Compound




P212



Rate



ppm











Fungicide name
0
50















—
0
4













Tiadinil
Rate
0.5
0
18



Isotianil
ppm
0.5
66
72

















TABLE 107







(Rice blast test 2)










Compound




P212



Rate



ppm











Fungicide name
0
50















—
0
16













Orysastrobin
Rate
0.5
20
91



Tricyclazole
ppm
0.5
72
92



Diclocymet

0.5
8
52



Tebufloquin

0.5
48
72

















TABLE 108







(Rice blast test 3)










Compound P212




Rate ppm












Fungicide name

0
50















—
0
0













Azoxystrobin
Rate
0.5
37
35



Kasugamycin
ppm
0.5
0
37










Test Example 12 Test of Control of Rice Sheath Blight (Rhizoctonia solani)
Six weeks after planting, rice seedlings were subjected to foliar spray treatment with a drug solution of the compound of Formula (I), or a drug solution of a mixture of a compound of Formula (I) and a fungicide as indicated below, prepared in a predetermined concentration with 10% acetone water. After an air drying process, a plug of growing Rhizoctonia solani (1.0 cm2 agar square each) was allowed to stand at the base of the rice. This was followed by holding in a thermostatic chamber (30° C. 15 day-25° C. night, 16 hours of light period-8 hours of dark period). Six days after the inoculation, the lesion height was measured, and the preventive value was calculated by the following equation. The test was performed in duplicate.

Preventive value={(lesion height in a zone without treatment−lesion height in a zone with treatment)/(lesion height in a zone without treatment)}×100

As a result, it was demonstrated that, at a treatment concentration of 5 ppm using thifluzamide, furametpyr, pencycuron, azoxystrobin, simeconazole, validamycin, or orysastrobin, the mixed agent with 50 ppm Compound P212 presented the same fungicidal effect as for treatment with thifluzamide, furametpyr, pencycuron, azoxystrobin, simeconazole, validamycin, or orysastrobin alone, and mixed treatment with a fungicide is therefore possible.







TABLE 109







(Sheath blight test 1)










Compound P212




Rate ppm












Fungicide name

0
50















—
0
14













Thifluzamide
Rate
5
92
97



Furametpyr
ppm
5
77
94



Pencycuron

5
69
77

















TABLE 110







(Sheath blight test 2)










Compound P212




Rate ppm












Fungicide name

0
50















—
0
9













Azoxystrobin
Rate
5
95
100



Simeconazole
ppm
5
5
24



Validamycin

5
32
74



Orysastrobin

5
72
59










Test Example 13 Test with Laodelphax striatellus by Treatment During the Vegetative Phase
Rice was planted in nursery boxes and emergence was carried out for three days a 30° C. followed by transfer of the nursery boxes to a glass greenhouse at 25° C. During the vegetative phase five days after planting, the nursery boxes were treated with a prescribed amount of a mixed granule of 0.24 mg/mg probenazole (24%) and 0.02 mg/mg Compound P212 (2%). The rice seedlings were transplanted to 1/5000a Wagner pots 22 days after planting and were grown in a greenhouse at 25° C. Second instar larvae of 15 Laodelphax striatellus were released at 13, 26, and 38 days post-transplantation to the Wagner pots; this was followed by holding in a glass greenhouse at 25° C. Five days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

According to the results, it was shown that the mixed granule of probenazole and Compound P212 presented a high insecticidal effect of 100% mortality and exhibited control at a practical level.
Test Example 14 Test with Laodelphax striatellus by Soil Irrigation Treatment
Rice seedlings in pot cultivation were subjected to a soil irrigation treatment with a drug solution of a compound of Formula (I) or a drug solution of a mixture of a compound of Formula (I) and a paddy herbicide as indicated below, prepared in predetermined concentrations so as to be a 10% acetone water. After standing for three 20 days, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. five days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

The mixed agent of Imazosulfuron, cafenstrole, cyhalofop-butyl, daimuron and pyrazolate tested with the Compound P212 was shown in all instances to exhibit an insecticidal effect at least equal to that for treatment with Compound P212 by itself, and a mixed treatment with a herbicide is thus possible.










TABLE 111









Compound P212




Rate mg/seedling












Herbicide name
0
0.005
0.01













—
0
0
100












Imazosulfuron
Rate
0.05
0
0
100


Cafenstrole
mg/seedling
0.05
0
0
100


Cyhalofop-

0.05
0
0
100


butyl


Daimuron

0.05
0
0
100


Pyrazolate

0.05
0
0
100









Test Example 15 Test of the Control of Haemaphysalis longicornis 
A capsule with a diameter of 2 cm and a height of 2 cm was attached to the dorsal surface of a mouse. A compound of Formula (I), ivermectin, moxidectin, permethrin, amitraz, fipronil, spinetram and the mixture of the compound of Formula (I) and each insecticide were dissolved in ethanol at the concentrations given in Table O, and each of these was dripped onto the surface of a mouse body within a capsule. After thorough drying, eight Haemaphysalis longicornis nymphs were released and the top of the capsule was sealed with a lid. The mouse was kept in a cage at 25° C. using a 12-hour light period and a 12-hour dark period. Five days after the release, the capsule was removed and the number of surviving and dead nymphs and the number of engorged individuals were counted and the insect mortality and agonal rate was calculated by the following equation.

Insect mortality and agonal rate (%)={number of dead and agonal insects/(number of survived insects+number of dead and agonal insects)}×100

The results showed that, at a rate of 0.009 μg of ivermectin or moxidectin, the mixed agent of either with Compound P212 also gave a tick control effect that was the same as treatment with ivermectin, moxidectin, permethrin, amitraz, fipronil and spinetram alone and mixed treatment with ivermectin, moxidectin, permethrin, amitraz, fipronil and spinetram is thus possible.







TABLE 112







Mortality (%) of single agent and mixed


agent against Haemaphysalis longicornis(1)










Compound P212




Rate μg












Insecticide name

0
1.18















—
0
53













Ivermectin
Rate
0.009
3
53



Moxidectin
μg
0.009
6
44

















TABLE 113







Mortality (%) of single agent and mixed


agent against Haemaphysalis longicornis(2)










Compound P212




Rate μg












Insecticide name

0
1.18















—
0
60













Amitraz
Rate
0.38
41
90



Permethrin
μg
9.5
71
86

















TABLE 114







Theoretical value (%) by Colby's equation










Compound P212




Rate μg












Insecticide name

0
1.18















—
0
60













Amitraz
Rate
0.38
41
77



Permethrin
μg
9.5
71
88

















TABLE 115







Mortality (%) of single agent and mixed


agent against Haemaphysalis longicornis(3)










Compound P212




Rate μg












Insecticide name

0
1.18















—
0
38













fipronil
Rate
0.38
78
93



spinetoram
μg
0.38
6
22

















TABLE 116







Theoretical value (%) by Colby's equation










Compound P212




Rate μg












Insecticide name

0
1.18















—
0
38













fipronil
Rate
0.38
78
86



spinetoram
μg
0.38
6
41

















TABLE 117







Mortality (%) of single agent and mixed


agent against Haemaphysalis longicornis(4)










Compound P212




Rate μg












Insecticide name

0
1.18















—
0
18













pyriproxyfen
Rate
0.0475
2
44



spinosad
μg
1.9
2.5
43

















TABLE 118







Theoretical value (%) by Colby's equation










Compound P212




Rate μg












Insecticide name

0
1.18















—
0
18













pyriproxyfen
Rate
0.0475
2
20



spinosad
μg
1.9
2.5
20

















TABLE 119







Mortality (%) of single agent and mixed


agent against Haemaphysalis longicornis(5)










Compound P212




Rate μg












Insecticide name

0
1.18















—
0
23













imidacloprid
Rate
1.9
7.7
60



dinotefuran
μg
1.9
0

















TABLE 120







Theoretical value (%) by Colby's equation










Compound P212




Rate μg












Insecticide name

0
1.18















—
0
23













imidacloprid
Rate
1.9
7.7
32



dinotefuran
μg
1.9
0
25

## Claims

1. A pest control composition comprising:
at least one iminopyridine derivative selected from the group consisting of N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide and acid addition salts thereof; and
at least one insecticide selected from the group consisting of thiamethoxam, pymetrozine, spinosad, fipronil, cyantraniliprole, silafluofen, sulfoxaflor, flupyradifurone, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, and agriculturally and/or zootechnically acceptable acid addition salts thereof.

2. A pest control composition comprising:
at least one iminopyridine derivative selected from the group consisting of N[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide and acid addition salts thereof; and
at least one fungicide selected from the group consisting of orysastrobin, thifluzamide, furametpyr, probenazole, tiadinil, isotianil, diclocymet, tricyclazole, tebufloquin, simeconazole, pencycuron, and agriculturally and/or zootechnically acceptable acid addition salts thereof.

3. A combined product comprising:
at least one iminopyridine derivative selected from the group consisting of N-[1((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide and acid addition salts thereof; and
at least one insecticide selected from the group consisting of thiamethoxam, pymetrozine, spinosad, fipronil, cyantraniliprole, silafluofen, sulfoxaflor, flupyradifurone, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, and agriculturally and/or zootechnically acceptable acid addition salts thereof.

4. A pest control composition comprising:
at least one iminopyridine derivative selected from the group consisting of N[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide and acid addition salts thereof; and
at least one other pest control agent, wherein the other pest control agent is a control agent for animal parasitic pests and is selected from the group consisting of fipronil, amitraz, pyriproxyfen, spinosad, and agriculturally and/or zootechnically acceptable acid addition salts thereof.

5. A combined product comprising:
at least one iminopyridine derivative selected from the group consisting of N-[1((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide and acid addition salts thereof; and
at least one fungicide selected from the group consisting of orysastrobin, thifluzamide, furametpyr, tiadinil, isotianil, diclocymet, tricyclazole, tebufloquin, simeconazole, pencycuron, and agriculturally and/or zootechnically acceptable acid addition salts thereof.

6. A combined product comprising:
at least one iminopyridine derivative selected from the group consisting of N-[1(6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide and acid addition salts thereof; and
at least one other pest control agent, wherein the other pest control agent is a control agent for animal parasitic pests and is selected from the group consisting of fipronil, amitraz, pyriproxyfen, spinosad, and agriculturally and/or zootechnically acceptable acid addition salts thereof.

7. A method for protecting useful plants or animals from pests comprising
simultaneously or independently applying the pest control composition of claim 1, 2 or 4 to a region to be treated.

8. A method for protecting useful plants or animals from pests by treating pests, useful plants, seeds of useful plants, soil, cultivation carriers or animals as a target, with an effective amount of the pest control composition of claim 1, 2 or 4.

9. A method for protecting useful plants or animals from pests by applying the combined product of claim 3, 5 or 6 to pests, useful plants, seeds of useful plants, soil, cultivation carriers or animals as a target.