# Patent

## Title
N-(oxazol-2-yl)-aryl-carboxylic acid amides and use thereof as herbicides

## Abstract

N-(Oxazol-2-yl)-aryl-carboxylic acid amides and use thereof as herbicides N-(Isoxazol-3-yl)arylcarboxamides and their use as herbicides are described.




In this formula (I), A represents N or C—Y. R, R′, V, X, Y and Z represent radicals such as hydrogen, halogen and organic radicals such as substituted alkyl.

## Background
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a §371 National Stage Application of PCT/EP2013/075297, filed 3 Dec. 2013, which claims priority to EP 12195959.7, filed 6 Dec. 2012.
BACKGROUND
Field of the Invention
The invention relates to the technical field of the herbicides, especially that of the herbicides for selective control of broad-leaved weeds and weed grasses in crops of useful plants.
Description of Related Art
WO 2011/035874 A1 discloses N-(1,2,5-oxadiazol-3-yl)benzamides and use thereof as herbicides. WO 2012/028579 A1 discloses N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides and their use as herbicides.
However, the compounds known from these documents exhibit zero or frequently inadequate herbicidal efficacy. It is an object of the present invention, therefore, to provide further herbicidally active compounds.
WO 2010/132404 A1 describes the pharmacologically active compound {[(5-methoxy-2-{[5-(2,2,2-trifluoroethyl)-1,3-oxazol-2-yl]carbamoyl}phenoxy)carbonyl]oxy}methyl 2,2-dimethylpropanoate.
Under the following CAS numbers, the compounds which are mentioned following each one are known:

    1187436-88-9: ethyl 4-methyl-2-({[2-methyl-6-(trifluoromethyl)pyridin-3-yl]carbonyl}amino)-1,3-oxazol-5-carboxylate.
    1090036-46-6: N-(4,5-dimethyl-1,3-oxazol-2-yl)-2,4-dimethylbenzamide.
    587008-52-4: 2,4-dichloro-N-(4,5-diphenyl-1,3-oxazol-2-yl)benzamide.


No herbicidal effect of the compounds known by their CAS numbers has been disclosed.
SUMMARY
It has now been found that N-(1,3-oxazol-2-yl)-arylcarboxamides which carry certain substituents in the arylcarboxylic acid moiety are particularly suitable for use as herbicides.
Accordingly, the present invention provides N-(1,3-oxazol-2-yl)arylcarboxamides of the formula (I) or salts thereof




in which

A represents N or CY,
R and R′ independently of one another each represent hydrogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C2-C6)-alkenyl, (C2-C6)-alkenyloxy, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-alkynyloxy, (C2-C6)-haloalkynyl, cyano-(C1-C6)-alkyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamine, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or heteroaryl, heterocyclyl or phenyl, each of which is substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
X represents nitro, halogen, cyano, formyl, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)NR1OR1, OR2, COOR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-OCOR1, (C1-C6)-alkyl-OSO2R2, (C1-C6)-alkyl-CO2R1, (C1-C6)-alkyl-SO2OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, NR1R2, P(O)(OR5)2, CH2P(O)(OR5)2, (C1-C6)-alkyl-heteroaryl, (C1-C6)-alkyl-heterocyclyl, where the two last-mentioned radicals are each substituted by s radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy and halo-(C1-C6)-alkoxy, and where heterocyclyl carries n oxo groups,
Y represents hydrogen, nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, CO(NOR1)R1, CHNOR1, CH2ONCR3)2, NR1SO2R2, NR1COR1, OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2 (C1-C6)-alkyl-S(O)nR2, NS(O)R8R7, S(O)R8NR9, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-OCOR1, (C1-C6)-alkyl-OSO2R2, (C1-C6)-alkyl-CO2R1, (C1-C6)-alkyl-CN, (C1-C6)-alkyl-SO2OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, N(R1)2, P(O)(OR5)2, CH2P(O)(OR5)2, (C1-C6)-alkylphenyl, (C1-C6)-alkylheteroaryl, (C1-C6)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the 6 last-mentioned radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C4)-alkyl and cyanomethyl, and where heterocyclyl carries n oxo groups,
Z represents halogen, cyano, thiocyanato, nitro, (C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)NR1OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-OCOR1, (C1-C6)-alkyl-OSO2R2, (C1-C6)-alkyl-CO2R1, (C1-C6)-alkyl-SO2OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, NR1R2, P(O)(OR5)2, heteroaryl, heterocyclyl or phenyl, where the three last-mentioned radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy or halo-(C1-C6)-alkoxy, and where heterocyclyl carries 0 to 2 oxo groups, or
Z may also represent hydrogen if Y represents the S(O)nR2 radical,
V represents hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, S(O)n—(C1-C6)-alkyl, S(O)n—(C1-C6)-haloalkyl, (C1-C6)-alkoxy-(C1-C4)-alkyl, halogen, nitro or cyano,
R1 represents hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O—(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocycl, (C1-C6)-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR3-heteroaryl, (C1-C6)-alkyl-NR3-heterocyclyl, where the 21 last-mentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4, CO2R3, COSR4, CON(R3)2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R2 represents (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O—(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, (C1-C6)-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR3-heteroaryl, (C1-C6)-alkyl-NR3-heterocyclyl, where the 21 last-mentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4, CO2R3, COSR4, CON(R3)2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R3 represents hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl,
R4 represents (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl or phenyl,
R5 represents methyl or ethyl,
R6 and R7 independently of one another each represent (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, halo-(C1-C6)-alkoxy-(C1-C6)-alkyl, phenyl, heteroaryl or heterocyclyl, where the three last-mentioned radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R1O(O)C, (R1)2N(O)C, R1O, (R1)2N, R2(O)nS, R1O(O)2S, (R1)2N(O)2S and R1O—(C1-C6)-alkyl, and where heterocyclyl carries n oxo groups,
or
R6 and R7 together with the sulfur atom to which they are attached form a 3- to 8-membered unsaturated, partly saturated or saturated ring which contains, apart from the carbon atoms and apart from the sulfur atom of the sulfoximino group, in each case m ring members from the group consisting of N(R1), O and S(O)n, and where this ring is in each case substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R1O(O)C, (R1)2N(O)C, R1O, (R1)2N, R2(O)nS, R1O(O)2S, (R1)2N(O)2S and R1O—(C1-C6)-alkyl, and where this ring carries n oxo groups,
R8 represents (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, each of which is substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C3-C6)-cycloalkyl, R1(O)C, R1(R1ON═)C, R1O(O)C, (R1)2N(O)C, R1(R1O)N(O)C, R2(O)2S(R1)N(O)C, R1O(O)2S(R1)N(O)C, (R1)2N(O)2S(R1)N(O)C, R1S(O)C, R1O, R1(O)CO, R2(O)2SO, R2O(O)CO, (R1)2N(O)CO, (R1)2N, R1O(R1)N, R1(O)C(R1)N, R2(O)2S(R1)N, R2O(O)C(R1)N, (R1)2N(O)C(R1)N, R1O(O)2S(R1)N, (R1)2N(O)2S(R1)N, R2(O)nS, R1C(O)S, R1O(O)2S, (R1)2N(O)2S, R1(O)C(R1)N(O)2S, R2O(O)C(R1)N(O)2S, (R1)2N(O)C(R1)N(O)2S and (R5O)2(O)P,
or
(C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, heteroaryl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, phenyl-O—(C1-C6)-alkyl, heteroaryl-O—(C1-C6)-alkyl, heterocyclyl-O—(C1-C6)-alkyl, phenyl-N(R1)—(C1-C6)-alkyl, heteroaryl-N(R1)—(C1-C6)-alkyl, heterocyclyl-N(R1)—(C1-C6)-alkyl, phenyl-S(O)n—(C1-C6)-alkyl, heteroaryl-S(O)n—(C1-C6)-alkyl or heterocyclyl-S(O)n—(C1-C6)-alkyl, each of which is substituted in the cyclic moiety by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R1(O)C, R1(R1ON═)C, R1O(O)C, (R1)2N(O)C, R1(R1O)N(O)C, R2(O)2S(R1)N(O)C, R1O(O)2S(R1)N(O)C, (R1)2N(O)2S(R1)N(O)C, R1S(O)C, R1O, R1(O)CO, R2(O)2SO, R2O(O)CO, (R1)2N(O)CO, (R1)2N, R1O(R1)N, R1(O)C(R1)N, R2(O)2S(R1)N, R2O(O)C(R1)N, (R1)2N(O)C(R1)N, R1O(O)2S(R1)N, (R1)2N(O)2S(R1)N, R2(O)nS, R1C(O)S, R1O(O)2S, (R1)2N(O)2S, R1(O)C(R1)N(O)2S, R2O(O)C(R1)N(O)2S, (R1)2N(O)C(R1)N(O)2S, (R5O)2(O)P and R1O—(C1-C6)-alkyl, and where heterocyclyl carries n oxo groups,
R9 represents hydrogen, nitro, halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-alkenyl, halo-(C3-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, R1(O)C, R2O(O)C, (R1)2N(O)C, R2S(O)C, (R1)2N(S)C, R1(R1O)N(O)C, R2(O)2S(R1)N(O)C, (R1)2N(O)2S(R1)N(O)C, R1O, (R1)2N, R2(O)nS, (R2)3Si—(C1-C6)-alkyl-(O)nS, R1O(O)2S, (R1)2N(O)2S, R1(O)C(R1)N(O)2S, R2O(O)C(R1)N(O)2S, (R1)2N(O)C(R1)N(O)2S, R2(O)2S(R1)N(O)2S, (R5O)2(O)P, (R2)3Si, R1(O)C—(C1-C6)-alkyl, R1O(O)C—(C1-C6)-alkyl, (R1)2N(O)C—(C1-C6)-alkyl, (R1O)(R1)N(O)C—(C1-C6)-alkyl, R2(O)2S(R1)N(O)C—(C1-C6)-alkyl, R1O(O)2S(R1)N(O)C—(C1-C6)-alkyl, (R1)2N(O)2S(R1)N(O)C—(C1-C6)-alkyl, R1O—(C1-C6)-alkyl, R1(O)CO—(C1-C6)-alkyl, R2(O)2SO—(C1-C6)-alkyl, R2O(O)CO—(C1-C6)-alkyl, (R1)2N(O)CO—(C1-C6)-alkyl, (R1)2N—(C1-C6)-alkyl, R1(O)C(R1)N—(C1-C6)-alkyl, R2(O)2S(R1)N—(C1-C6)-alkyl, R2O(O)C(R1)N—(C1-C6)-alkyl, (R1)2N(O)C(R1)N—(C1-C6)-alkyl, R1O(O)2S(R1)N—(C1-C6)-alkyl, (R1)2N(O)2S(R1)N—(C1-C6)-alkyl, R2(O)nS—(C1-C6)-alkyl, R1O(O)2S—(C1-C6)-alkyl, (R1)2N(O)2S—(C1-C6)-alkyl, R1(O)C(R1)N(O)2S—(C1-C6)-alkyl, R2O(O)C(R1)N(O)2S—(C1-C6)-alkyl, (R1)2N(O)C(R1)N(O)2S—(C1-C6)-alkyl, (R5O)2(O)P—(C1-C6)-alkyl, (R2)3Si—(C1-C6)-alkyl,
or
phenyl, heteroaryl, heterocyclyl, phenyl-(C1-C6)-alkyl, heteroaryl-(C1-C6)-alkyl or heterocyclyl-(C1-C6)-alkyl, each of which is substituted in the cyclic moiety by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R1O(O)C, (R1)2N(O)C, R1O, (R1)2N, R2(O)nS, R1O(O)2S, (R1)2N(O)2S and R1O—(C1-C6)-alkyl, and where heterocyclyl carries n oxo groups,
m represents 0, 1, 2, 3 or 4,
n represents 0, 1 or 2,
s represents 0, 1, 2 or 3,
except for the compounds {[(5-methoxy-2-{[5-(2,2,2-trifluoroethyl)-1,3-oxazol-2-yl]carbamoyl}phenoxy)carbonyl]oxy}methyl 2,2-dimethylpropanoate, ethyl 4-methyl-2-({[2-methyl-6-(trifluoromethyl)pyridin-3-yl]carbonyl}amino)-1,3-oxazol-5-carboxylate, N-(4,5-dimethyl-1,3-oxazol-2-yl)-2,4-dimethylbenzamide and 2,4-dichloro-N-(4,5-diphenyl-1,3-oxazol-2-yl)benzamide.


DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT
In the formula (I) and all the formulae which follow, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.
Heterocyclyl is a saturated, partly saturated or fully unsaturated cyclic radical which contains 3 to 6 ring atoms, of which 1 to 4 are from the group of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl.
Heteroaryl represents an aromatic cyclic radical which contains 3 to 6 ring atoms, of which 1 to 4 are from the group of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring. For example, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.
If a group is polysubstituted by radicals, this is understood to mean that this group is substituted by one or more identical or different radicals from those mentioned.
Depending on the nature of the substituents and the manner in which they are attached, the compounds of the general formula (I) may be present as stereoisomers. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers likewise occur when n is 1 (sulfoxides).
Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation processes. It is likewise possible to selectively prepare stereoisomers by using stereoselective reactions with use of optically active starting materials and/or auxiliaries. The invention also relates to all the stereoisomers and mixtures thereof that are encompassed by the general formula (I) but are not defined specifically.
Preference is given to compounds of the general formula (I) in which
A represents N or CY,
X represents nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, C1-C6)-alkyl-O—(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR1, OR2, OCOR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-COOR1, (C1-C6)-alkyl-OSO2R2, (C1-C6)-alkyl-CO2R1, (C1-C6)-alkyl-SO2OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1 or (C1-C6)-alkyl-NR1SO2R2, (C1-C6)-alkylheteroaryl, (C1-C6)-alkylheterocyclyl, where the two last-mentioned radicals each by s radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy and halo-(C1-C6)-alkoxy, and where heterocyclyl carries n oxo groups,
Y represents hydrogen, nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR1, OR1, COOR1, OSO2R2, S(O)nR2, SO2OR1, SO2 N(R1)2, N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-OCOR1, (C1-C6)-alkyl-OSO2R2, (C1-C6)-alkyl-CO2R1, (C1-C6)-alkyl-SO2OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, (C1-C6)-alkylphenyl, (C1-C6)-alkyl-heteroaryl, (C1-C6)-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, where the 6 last-mentioned radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C4)-alkyl and cyanomethyl, and where heterocyclyl carries n oxo groups,
Z represents halogen, cyano, thiocyanato, nitro, (C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR1, COOR1, C(O)N(R1)2, C(O)NR1OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-OCOR1, (C1-C6)-alkyl-OSO2R2, (C1-C6)-alkyl-CO2R1, (C1-C6)-alkyl-SO2OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, 1,2,4-triazol-1-yl, or
Z may also represent hydrogen if Y represents the S(O)nR2 radical,
V represents hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, S(O)n—(C1-C6)-alkyl, S(O)n—(C1-C6)-haloalkyl, (C1-C6)-alkoxy-(C1-C4)-alkyl, halogen, nitro or cyano,
R, R′ independently of one another each represent hydrogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, cyano-(C1-C6)-alkyl, cyano, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, methoxymethyl, or heteroaryl, heterocyclyl or phenyl, each of which is substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
R1 represents hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O—(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, (C1-C6)-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR3-heteroaryl or (C1-C6)-alkyl-NR3-heterocyclyl, where the 16 last-mentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, NR3COR3, NR3SO2R4, CO2R3, CON(R3)2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R2 represents (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O—(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, (C1-C6)-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR3-heteroaryl or (C1-C6)-alkyl-NR3-heterocyclyl, where these radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, NR3SO2R4, COR3, OCOR3, NR3COR3, CO2R3, CON(R3)2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R3 represents hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl,
R4 represents (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl,
R6 and R7 independently of one another each represent (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, halo-(C1-C6)-alkoxy-(C1-C6)-alkyl, phenyl, heteroaryl or heterocyclyl, where the three last-mentioned radicals are each substituted by s radicals from the group consisting of nitro, halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R1O(O)C, (R1)2N(O)C, R1O, (R1)2N, R2(O)nS and R1O—(C1-C6)-alkyl, and where heterocyclyl carries n oxo groups,
or R6 and R7 together with the sulfur atom to which they are attached form a 3- to 8-membered unsaturated, partly saturated or saturated ring which contains, in addition to the carbon atoms and in addition to the sulfur atom of the sulfoximino group, in each case m ring members from the group consisting of N(R1), O and S(O)n, and where this ring is in each case substituted by s radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R1O(O)C, (R1)2N(O)C, R1O, (R1)2N, R2(O)nS, R1O(O)2S, (R1)2N(O)2S and R1O—(C1-C6)-alkyl, and where this ring carries n oxo groups,
R8 represents (C1-C6)-alkyl which is in each case substituted by s radicals from the group consisting of halogen, cyano, (C3-C6)-cycloalkyl, R1(O)C, R1(R1ON═)C, R1O(O)C, (R1)2N(O)C, R2(O)2S(R1)N(O)C, R1O, (R1)2N, R1(O)C(R1)N, R2(O)2S(R1)N, R2O(O)C(R1)N, (R1)2N(O)C(R1)N, R2(O)nS, R1O(O)2S, (R1)2N(O)2S, R1(O)C(R1)N(O)2S, R2O(O)C(R1)N(O)2S and (R1)2N(O)C(R1)N(O)2S or (C3-C6)-cycloalkyl which is in each case substituted by s radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R1O(O)C and (R1)2N(O)C,
R9 represents hydrogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, R1(O)C, R2O(O)C, (R1)2N(O)C, R2(O)2S, R1(O)C—(C1-C6)-alkyl, R1O(O)C—(C1-C6)-alkyl, (R1)2N(O)C—(C1-C6)-alkyl, R1O—(C1-C6)-alkyl, (R1)2N—(C1-C6)-alkyl or R2(O)nS—(C1-C6)-alkyl,
m represents 0, 1 or 2,
n represents 0, 1 or 2,
s represents 0, 1, 2 or 3.
Particular preference is given to compounds of the general formula (I) in which A represents N or CY,
X represents nitro, halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, OR2, S(O)nR2, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, (C1-C6)-alkylheteroaryl, (C1-C6)-alkylheterocyclyl, where the two last-mentioned radicals are each substituted by s radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, and where heterocyclyl carries n oxo groups,
Y hydrogen, nitro, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, OR1, S(O)nR2, SO2N(R1)2, N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, (C1-C6)-alkylphenyl, (C1-C6)-alkylheteroaryl, (C1-C6)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the 6 last-mentioned radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C4)-alkyl and cyanomethyl, and where heterocyclyl carries n oxo groups,
Z represents halogen, cyano, nitro, (C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O)nR2, 1,2,4-triazol-1-yl, or Z may also represent hydrogen if Y represents the S(O)nR2 radical,
V represents hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, S(O)n—(C1-C6)-alkyl, S(O)n—(C1-C6)-haloalkyl, (C1-C6)-alkoxy-(C1-C4)-alkyl, halogen, nitro or cyano,
R, R′ independently of one another each represent hydrogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, cyano-(C1-C6)-alkyl, cyano, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, halogen, amino, methoxymethyl,
R1 represents hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O—(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, (C1-C6)-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR3-heteroaryl or (C1-C6)-alkyl-NR3-heterocyclyl, where the 16 last-mentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, COW, OCOR3, NR3COR3, NR3SO2R4, CO2R3, CON(R3)2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R2 represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl, where these three radicals mentioned above are each substituted by s radicals from the group consisting of halogen and OR3,
R3 represents hydrogen or (C1-C6)-alkyl,
R4 represents (C1-C6)-alkyl,
R6 and R7 independently of one another each represent methyl, ethyl or n-propyl, or
R6 and R7 together with the sulfur atom to which they are attached form a 5- or 6-membered saturated ring which, in addition to the carbon atoms and in addition to the sulfur atom of the sulfoximino group, contains m oxygen atoms,
R8 represents methyl, ethyl or n-propyl,
R9 represents hydrogen or cyano,
m represents 0 or 1,
n represents 0, 1 or 2,
s represents 0, 1, 2 or 3.
In all the formulae specified hereinafter, the substituents and symbols have the same meaning as described in formula (I), unless defined differently.
Compounds according to the invention can be prepared, for example, by the method shown in scheme 1, by base-catalyzed reaction of a benzoyl chloride (II) with a 2-amino-1,3-oxazole (III):




Compounds according to the invention can also be prepared by the method described in scheme 2, by reacting a benzoic acid of the formula (IV) with a 2-amino-1,3-oxazole (III):




For the activation, it is possible to use dehydrating reagents which are typically for amidation reactions, for example 1,1′-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P), etc.
It may be expedient to change the order of reaction steps. Thus, benzoic acids carrying a sulfoxide cannot be converted directly into their acid chlorides. Here, it is advisable to prepare initially, at the thioether stage, the amide and then to oxidize the thioether to the sulfoxide.
The benzoyl chlorides of the formula (II) or the parent benzoic acids thereof (IV) are known in principle and can be prepared, for example, by the methods described in U.S. Pat. No. 6,376,429 B1, EP 1 585 742 A1 and EP 1 202 978 A1.
The 2-amino-1,3-oxazoles of the formula (III) are either commercially available or can be prepared analogously to methods known from the literature.
Collections of compounds of the formula (I) and/or salts thereof which can be synthesized by the abovementioned reactions can also be prepared in a parallelized manner, in which case this may be accomplished in a manual, partly automated or fully automated manner. It is possible, for example, to automate the conduct of the reaction, the work-up or the purification of the products and/or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry—Synthesis, Analysis, Screening (editor Gunther Jung), Wiley, 1999, on pages 1 to 34.
For the parallelized conduct of the reaction and workup, it is possible to use a number of commercially available instruments, for example Calypso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB11 3AZ, England, or MuItiPROBE Automated Workstations from PerkinElmer, Waltham, Mass. 02451, USA. For the parallelized purification of compounds of the general formula (I) and salts thereof or of intermediates which occur in the course of preparation, available apparatuses include chromatography apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.
The apparatuses detailed lead to a modular procedure in which the individual working steps are automated, but manual operations have to be carried out between the working steps. This can be circumvented by using partly or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Automation systems of this type can be obtained, for example, from Caliper, Hopkinton, Mass. 01748, USA.
The implementation of single or multiple synthesis steps can be supported by the use of polymer-supported reagents/scavenger resins. The specialist literature describes a series of experimental protocols, for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).
Aside from the methods described here, compounds of the general formula (I) and salts thereof can be prepared completely or partially by solid-phase-supported methods. For this purpose, individual intermediates or all intermediates in the synthesis or a synthesis adapted for the corresponding procedure are bound to a synthesis resin. Solid-phase-supported synthesis methods are described adequately in the technical literature, for example Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis, Analysis, Screening (editor: Gunther Jung), Wiley, 1999. The use of solid-phase-supported synthesis methods permits a number of protocols, which are known from the literature and which for their part may be performed manually or in an automated manner. The reactions can be performed, for example, by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.
Both in the solid and in the liquid phase, individual or several synthesis steps may be supported by the use of microwave technology. The specialist literature describes a series of experimental protocols, for example in Microwaves in Organic and Medicinal Chemistry (editor: C. O. Kappe and A. Stadler), Wiley, 2005.
The preparation by the processes described here gives compounds of the formula (I) and salts thereof in the form of substance collections, which are called libraries. The present invention also provides libraries comprising at least two compounds of the formula (I) and salts thereof.
The compounds of the formula (I) according to the invention (and/or salts thereof), referred to collectively as “compounds according to the invention” hereinafter, have excellent herbicidal efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active compounds also have good control over perennial harmful plants which are difficult to control and produce shoots from rhizomes, root stocks or other perennial organs.
The present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, in which one or more compound(s) according to the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), the seed (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or the area on which the plants grow (for example the area under cultivation). The compounds according to the invention can be deployed, for example, prior to sowing (if appropriate also by incorporation into the soil), prior to emergence or after emergence. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention are as follows, though the enumeration is not intended to impose a restriction to particular species.
Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. 
Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. 
If the compounds according to the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely or the weeds grow until they have reached the cotyledon stage, but then they stop growing and ultimately die completely after three to four weeks have passed.
If the active compounds are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage of the time of application, or they die completely after a certain time, such that competition by the weeds, which is harmful to the crop plants, is thus eliminated very early and in a lasting manner.
Although the compounds according to the invention have outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, will be damaged to a negligible extent only, if at all, depending on the structure of the particular compound according to the invention and its application rate. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamental plants.
In addition, the compounds according to the invention (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plants' own metabolism with regulatory effect, and can thus be used for controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. In addition, they are also suitable for general control and inhibition of unwanted vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous plants since, for example, this can reduce or completely prevent lodging.
By virtue of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, transgenic plants are notable for particular advantageous properties, for example for resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or with a different fatty acid composition in the harvested material.
It is preferable, with respect to transgenic crops, to use the compounds according to the invention in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet/sorghum, rice and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other types of vegetable. It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.
Preference is given to the use of the compounds according to the invention or salts thereof in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet/sorghum, rice, cassava and corn, or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other types of vegetable. Preferably, the compounds according to the invention can be used as herbicides in crops of useful plants which are resistant, or have been made resistant by genetic engineering, to the phytotoxic effects of the herbicides.
Conventional ways of producing novel plants which have modified properties in comparison to plants which have occurred to date consist, for example, in traditional breeding methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, there have been descriptions in several cases of:

    
    
        genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, WO 91/19806),
        transgenic crop plants which are resistant to particular herbicides of the glufosinate type (cf., for example, EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or of the sulfonylureas (EP-A-0257993, USA 5013659),
        transgenic crop plants, for example cotton, capable of producing Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to particular pests (EP-A-0142924, EP-A-0193259),
        transgenic crop plants with a modified fatty acid composition (WO 91/13972),
        genetically modified crop plants with novel constituents or secondary metabolites, for example novel phytoalexins, which bring about an increased disease resistance (EPA 309862, EPA0464461),
        genetically modified plants having reduced photorespiration, which have higher yields and higher stress tolerance (EPA 0305398),
        transgenic crop plants which produce pharmaceutically or diagnostically important proteins (“molecular pharming”),
        transgenic crop plants which feature higher yields or better quality,
        transgenic crop plants which feature a combination, for example, of the abovementioned novel properties (“gene stacking”).
    
    


A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, “Trends in Plant Science” 1 (1996) 423-431).
For such recombinant manipulations, nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it is possible, for example, to undertake base exchanges, remove parts of sequences or add natural or synthetic sequences. For the joining of the DNA fragments to one another, adaptors or linkers can be attached to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene and Klone” [Genes and Clones], VCH Weinheim 2nd edition 1996
For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product. To this end, it is firstly possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them.
When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acid molecules can also be expressed in the organelles of the plant cells.
The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants.
Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.
The compounds according to the invention can be used with preference in transgenic crops which are resistant to growth regulators, for example dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active compounds.
When the active compounds according to the invention are used in transgenic crops, not only do the effects toward harmful plants which are observed in other crops occur, but often also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.
The invention therefore also provides for the use of the compounds according to the invention as herbicides for control of harmful plants in transgenic crop plants.
The compounds according to the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant-growth-regulating compositions which comprise the compounds according to the invention.
The compounds according to the invention can be formulated in various ways, according to the biological and/or physicochemical parameters required. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), seed-dressing products, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.
The formulation auxiliaries required, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical Engineering], volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
On the basis of these formulations, it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides, fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tankmix. Suitable safeners are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichlormid.
Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active compound, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethlated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatus such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.
Emulsifiable concentrates are produced by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonate salts such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.
Dustable powders are obtained by grinding the active compound with finely distributed solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspension concentrates may be water- or oil-based. They may be prepared, for example, by wet-grinding by means of commercial bead mills and optional addition of surfactants as have, for example, already been listed above for the other formulation types.
Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types.
Granules can be prepared either by spraying the active compound onto adsorptive granular inert material or by applying active compound concentrates to the surface of carriers, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner customary for the production of fertilizer granules—if desired as a mixture with fertilizers.
Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.
For the production of pan granules, fluidized bed granules, extruder granules and spray granules, see, for example, processes in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London, J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”, 5th ed., McGraw-Hill, New York 1973, pp. 8-57.
For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
The agrochemical preparations contain generally 0.1 to 99% by weight, especially 0.1 to 95% by weight, of compounds according to the invention.
In wettable powders, the active compound concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active compound concentration may be about 1 to 90% and preferably 5 to 80% by weight. Dust-type formulations contain 1% to 30% by weight of active compound, preferably usually 5% to 20% by weight of active compound; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends partially on whether the active compound is present in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
In addition, the active compound formulations mentioned optionally comprise the respective customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity.
On the basis of these formulations, it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides, fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tankmix.
For application, the formulations in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type formulations, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.
The required application rate of the compounds of the formula (I) varies with the external conditions, including temperature, humidity and the type of herbicide used. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha or more of active substance, but it is preferably between 0.005 and 750 g/ha.
The examples which follow illustrate the invention.
A. Chemical Examples
Synthesis of 2-chloro-4-(methylsulfonyl)-N-(1,3-oxazol-2-yl)-3-[(2,2,2-trifluoroethoxy)methyl]benzamide, (Table Example No. 1-334)
347 mg (1.0 mmol) of 2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoic acid and 84 mg (1.0 mmol) of 1,3-oxazole-2-amine are dissolved at room temperature (RT) in 7 ml of dichloromethane, and 0.14 ml (1.0 mmol) of triethylamine, 24 mg (0.20 mmol) of DMAP and 955 mg (1.5 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added. The reaction mixture is stirred at RT for 20 h and then washed twice with in each case 5 ml of water. The organic phase is dried over Na2SO4 and concentrated. The residue is purified by column chromatography (HPLC, acetonitrile/water). Yield 93 mg (20%).
Synthesis of 2-chloro-N-(4-methyl-1,3-oxazol-2-yl)-4-(methylsulfonyl)benzamide (Table example No. 7-13)
574 mg (2.0 mmol) of 2-chloro-4-methylsulfonylbenzoic acid and 240 mg (1.0 mmol) of 4-methyl-1,3-oxazole-2-amine are dissolved at RT in 7 ml of dichloromethane, and 0.34 ml (2.0 mmol) of triethylamine, 60 mg (0.49 mmol) of DMAP and 2.335 g (4 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added. The reaction mixture is stirred at RT for 20 h and then washed twice with in each case 5 ml of water. The organic phase is dried over Na2SO4 and concentrated. The residue is purified by column chromatography (HPLC, acetonitrile/water). Yield 66 mg (7.3%).
Synthesis of 2-chloro-N-(4-phenyl-1,3-oxazol-2-yl)-4-(methylsulfonyl)benzamide, (Table example No. 9-13)
293 mg (1.25 mmol) of 2-chloro-4-methylsulphonylbenzoic acid and 200 mg (1.25 mmol) of 4-phenyl-1,3-oxazol-2-amine are dissolved at RT in 7 ml of dichloromethane, and 0.17 ml (1.25 mmol) of triethylamine, 31 mg (0.25 mmol) of DMAP and 1.19 g (1.88 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added. The reaction mixture is stirred at RT for 20 h and then washed twice with in each case 5 ml of water. The organic phase is dried over Na2Sa4 and concentrated. The residue is purified by column chromatography (HPLC, acetonitrile/water). Yield 91 mg (17%).
Synthesis of 2-chloro-N-(1,3-oxazol-2-yl)-6-(trifluoromethyl)nicotinamide (Table example No. 10-1)
537 mg (2.38 mmol) of 2-Chloro-6-(trifluoromethyl)nicotinic acid and 200 mg (2.38 mmol) of 1,3-oxazol-2-amine are dissolved at RT in 7 ml of dichloromethane, and 0.33 ml (2.38 mmol) of triethylamine, 58 mg (0.47 mmol) of DMAP and 2.27 g (3.57 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added. The reaction mixture is stirred at RT for 20 h and then washed twice with in each case 5 ml of water. The organic phase is dried over Na2SO4 and concentrated. The residue is purified by column chromatography (HPLC, acetonitrile/water). Yield 40 mg (5%).
The examples listed in the tables below were prepared analogously to the abovementioned methods or are obtainable analogously to the abovementioned methods. The compounds listed in the tables below are very particularly preferred.
The abbreviations and terms used denote:
Et=ethyl Me=methyl n-Pr=n-propyl c-Pr=Cyclopropyl i-Pr=isopropyl Bn=benzyl Ph=phenyl Ac=acetyl t-Bu=tert-butyl











TABLE 1







Compounds of the general formula (I) according to the invention in which


R and R′ represents H and A represents C-Y.








 

















Physical data







(1H-NMR, DMSO-d6, 400


No.
X
Y
Z
V
MHz)





1-1 
F
H
F
H



1-2 
F
H
Cl
H



1-3 
F
H
SO2Me
H



1-4 
F
H
SO2Et
H



1-5 
F
H
CF3
H



1-6 
F
H
NO2
H



1-7 
Cl
H
F
H



1-8 
Cl
H
F
F



1-9 
Cl
H
Cl
H



1-10 
Cl
H
Br
H



1-11 
Cl
H
SMe
H



1-12 
Cl
H
SOMe
H



1-13 
Cl
H
SO2Me
H



1-14 
Cl
H
SO2Et
H



1-15 
Cl
H
CF3
H



1-16 
Cl
H
NO2
H



1-17 
Cl
H
pyrazol-1-yl
H



1-18 
Br
H
Cl
H



1-19 
Br
H
Br
H



1-20 
Br
H
SO2Me
H



1-21 
Br
H
SO2Et
H



1-22 
Br
H
CF3
H



1-23 
SO2Me
H
Cl
H



1-24 
SO2Me
H
Br
H



1-25 
SO2Me
H
SMe
H



1-26 
SO2Me
H
SOMe
H



1-27 
SO2Me
H
SO2Me
H



1-28 
SO2Me
H
SO2Et
H



1-29 
SO2Me
H
CF3
H



1-30 
SO2Et
H
Cl
H



1-31 
SO2Et
H
Br
H



1-32 
NO2
H
NO2
H



1-33 
SO2Et
H
SO2Me
H



1-34 
SO2Et
H
CF3
H



1-35 
CH2SO2Me
H
Br
H



1-36 
CH2SO2Me
H
CF3
H
12.03 (s, 1H), 7.95-7.86







(m, 4H), 7.17 (s, 1H), 4.97







(s, 2H), 2.96 (s, 3H)


1-37 
NO2
H
F
H



1-38 
NO2
H
Cl
H



1-39 
NO2
H
Br
H



1-40 
NO2
H
I
H



1-41 
NO2
H
CN
H



1-42 
NO2
H
SO2Me
H



1-43 
NO2
H
SO2Et
H



1-44 
NO2
H
CF3
H



1-45 
Me
H
F
H



1-46 
Me
H
Cl
H



1-47 
Me
H
Br
H



1-48 
Me
H
I
H



1-49 
Me
H
CN
H



1-50 
Me
H
SO2Me
H



1-51 
Me
H
SO2Et
H



1-52 
Me
H
CF3
H



1-53 
Et
H
F
H



1-54 
Et
H
Cl
H



1-55 
Et
H
Br
H



1-56 
Et
H
I
H



1-57 
Et
H
CN
H



1-58 
Et
H
SO2Me
H



1-59 
Et
H
SO2Et
H



1-60 
Et
H
CF3
H



1-61 
CF3
H
NO2
H



1-62 
CF3
H
Br
H



1-63 
CF3
H
CF3
H



1-64 
CF3
H
SO2Me
H



1-65 
CF3
H
SO2Et
H



1-66 
CF3
H
Cl
H



1-67 
NO2
NH2
F
H



1-68 
NO2
NHMe
F
H



1-69 
NO2
NMe2
F
H



1-70 
NO2
Me
Cl
H



1-71 
NO2
NH2
Cl
H



1-72 
NO2
NHMe
Cl
H



1-73 
NO2
NMe2
Cl
H



1-74 
NO2
NH2
Br
H



1-75 
NO2
NHMe
Br
H



1-76 
NO2
NMe2
Br
H



1-77 
NO2
NH2
CF3
H



1-78 
NO2
NMe2
CF3
H



1-79 
NO2
NH2
SO2Me
H



1-80 
NO2
NH2
SO2Et
H



1-81 
NO2
NHMe
SO2Me
H



1-82 
NO2
NMe2
SO2Me
H



1-83 
NO2
NMe2
SO2Et
H



1-84 
NO2
NH2
1H-1,2,4-
H






triazol-1-yl




1-85 
NO2
NHMe
1H-1,2,4-
H






triazol-1-yl




1-86 
NO2
NMe2
1H-1,2,4-
H






triazol-1-yl




1-87 
Me
F
F
H



1-88 
Me
F
Cl
H



1-89 
Me
Me
SO2Me
H



1-90 
Me
F
SO2Me
H



1-91 
Me
Cl
Cl
H



1-92 
Me
O(CH2)2OMe
Cl
H



1-93 
Me
O(CH2)3OMe
Cl
H



1-94 
Me
O(CH2)4OMe
Cl
H



1-95 
Me
OCH2CONMe2
Cl
H



1-96 
Me
O(CH2)2—CO—NMe2
Cl
H



1-97 
Me
O(CH2)2—NH(CO)NMe2
Cl
H



1-98 
Me
O(CH2)2—NH(CO)NHCO2Et
Cl
H



1-99 
Me
O(CH2)2—NHCO2Me
Cl
H



1-100
Me
OCH2—NHSO2cPr
Cl
H



1-101
Me
O(CH2)-5-2,4-dimethyl-
Cl
H





2,4-dihydro-3H-1,2,4-







triazol-3-yl





1-102
Me
O(CH2)-3,5-dimethyl-
Cl
H





1,2-oxazol-4-yl





1-103
Me
OCH2(CO)NMe2
Br
H



1-104
Me
O(CH2)-5-pyrrolidin-2-
Br
H





one





1-105
Me
Cl
CF3
H



1-106
Me
Me
SO2Me
H



1-107
Me
4,5-dihydro-1,2-oxazol-
SO2Me
H





3-yl





1-108
Me
4,5-dihydro-1,2-oxazol-
SO2Et
H





3-yl





1-109
Me
5-cyanomethyl-4,5-
SO2Me
H





dihydro-1,2-oxazol-3-yl





1-110
Me
5-cyanomethyl-4,5-
SO2Et
H





dihydro-1,2-oxazol-3-yl





1-111
Me
NHCH2C(O)NMe2
SO2Me
H



1-112
Me
SMe
Me
H



1-113
Me
SOMe
Me
H



1-114
Me
SO2Me
Me
H



1-115
Me
SEt
Me
H



1-116
Me
SOEt
Me
H



1-117
Me
SO2Et
Me
H



1-118
Me
S(CH2)2OMe
Me
H



1-119
Me
SO(CH2)2OMe
Me
H



1-120
Me
SO2(CH2)2OMe
Me
H



1-121
Me
SO2cPr
Me
H



1-122
Me
OH
SO2Me
H



1-123
Me
OMe
SO2Me
H



1-124
Me
OMe
SO2Et
H



1-125
Me
OEt
SO2Me
H



1-126
Me
OEt
SO2Et
H



1-127
Me
OiPr
SO2Me
H



1-128
Me
OiPr
SO2Et
H



1-129
Me
O(CH2)2OMe
SO2Me
H



1-130
Me
O(CH2)2OMe
SO2Et
H



1-131
Me
O(CH2)3OMe
SO2Me
H



1-132
Me
O(CH2)3OMe
SO2Et
H



1-133
Me
O(CH2)4OMe
SO2Me
H



1-134
Me
O(CH2)4OMe
SO2Et
H



1-135
Me
O(CH2)2NHSO2Me
SO2Me
H



1-136
Me
O(CH2)2NHSO2Me
SO2Et
H



1-137
Me
OCH2(CO)NMe2
SO2Me
H



1-138
Me
OCH2(CO)NMe2
SO2Et
H



1-139
Me
[1,4]dioxan-2-yl-
SO2Me
H





methoxy





1-140
Me
[1,4]dioxan-2-yl-
SO2Et
H





methoxy





1-141
Me
O(CH2)2—O-(3,5-di-
SO2Me
H





methoxypyrimidin-2-yl)





1-142
Me
Cl
SO2Me
H
8.01 (d, 1H), 7.95 (s, 1H),







7.70 (d, 1H), 7.18 (d, 1H),







3.42 (s, 3H), 2.42 (s, 1H)


1-143
Me
SMe
H
H



1-144
Me
SOMe
H
H



1-145
Me
SO2Me
H
H



1-146
Me
SEt
H
H



1-147
Me
SOEt
H
H



1-148
Me
SO2Et
H
H



1-149
Me
S(CH2)2OMe
H
H



1-150
Me
SO(CH2)2OMe
H
H



1-151
Me
SO2(CH2)2OMe
H
H



1-152
Me
SMe
F
H



1-153
Me
SOMe
F
H



1-154
Me
SO2Me
F
H



1-155
Me
SEt
F
H



1-156
Me
SOEt
F
H



1-157
Me
SO2Et
F
H



1-158
Me
S(CH2)2OMe
F
H



1-159
Me
SO(CH2)2OMe
F
H



1-160
Me
SO2(CH2)2OMe
F
H



1-161
Me
SMe
SO2Me
H



1-162
Me
SOMe
SO2Me
H



1-163
Me
SO2Me
SO2Me
H
8.23 (d, 1H), 8.01 (d, 1H),







7.94 (s, 1H), 7.19 (s, 1H),







3.59 (s, 3H), 3.55 (s, 3H),







2.68 (s, 3H)


1-164
Me
SO2Me
SO2Et
H



1-165
Me
SEt
SO2Me
H



1-166
Me
SOEt
SO2Me
H



1-167
Me
SO2Et
SO2Me
H



1-168
Me
S(CH2)2OMe
SO2Me
H



1-169
Me
SO(CH2)2OMe
SO2Me
H



1-170
Me
SO2(CH2)2OMe
SO2Me
H



1-171
Me
SMe
CF3
H
11.76 (s, 1H), 7.94 (s, 1H),







7.76 (d, 1H), 7.66 (d, 1H),







7.16 (s, 1H), 2.67 (s, 3H),







2.31 (s, 3H)


1-172
Me
SOMe
CF3
H
11.88 (s, 1H), 7.94 (s, 1H),







7.83 (d, 1H), 7.79 (d, 1H),







7.17 (s, 1H), 3.04 (s, 3H),







2.83 (s, 3H)


1-173
Me
SO2Me
CF3
H



1-174
Me
SEt
CF3
H



1-175
Me
SOEt
CF3
H



1-176
Me
SO2Et
CF3
H



1-177
Me
S(CH2)2OMe
CF3
H



1-178
Me
SO(CH2)2OMe
CF3
H



1-179
Me
SO2(CH2)2OMe
CF3
H



1-180
Me
SMe
Br
H



1-181
Me
SOMe
Br
H



1-182
Me
SO2Me
Br
H



1-183
Me
SEt
Br
H



1-184
Me
SOEt
Br
H



1-185
Me
SO2Et
Br
H



1-186
Me
SMe
I
H



1-187
Me
SOMe
I
H



1-188
Me
SO2Me
I
H



1-189
Me
SEt
I
H



1-190
Me
SOEt
I
H



1-191
Me
SO2Et
I
H



1-192
Me
SMe
Cl
H



1-193
Me
SOMe
Cl
H



1-194
Me
SO2Me
Cl
H



1-195
Me
SEt
Cl
H



1-196
Me
SOEt
Cl
H



1-197
Me
SO2Et
Cl
H



1-198
Me
S(CH2)2OMe
Cl
H



1-199
Me
SO(CH2)2OMe
Cl
H



1-200
Me
SO2(CH2)2OMe
Cl
H



1-201
CH2SMe
OMe
SO2Me
H



1-202
CH2OMe
OMe
SO2Me
H



1-203
CH2O(CH2)2OMe
NH(CH2)2OEt
SO2Me
H



1-204
CH2O(CH2)2OMe
NH(CH2)3OEt
SO2Me
H



1-205
CH2O(CH2)3OMe
OMe
SO2Me
H



1-206
CH2O(CH2)2OMe
NH(CH2)2OMe
SO2Me
H



1-207
CH2O(CH2)2OMe
NH(CH2)3OMe
SO2Me
H



1-208
Et
SMe
Cl
H



1-209
Et
SOMe
Cl
H



1-210
Et
SO2Me
Cl
H



1-211
Et
SMe
CF3
H



1-212
Et
SOMe
CF3
H



1-213
Et
SO2Me
CF3
H



1-214
Et
F
SO2Me
H



1-215
Et
NH(CH2)2OMe
SO2Me
H



1-216
iPr
SMe
CF3
H



1-217
iPr
SOMe
CF3
H



1-218
iPr
SO2Me
CF3
H



1-219
cPr
SMe
CF3
H



1-220
cPr
SOMe
CF3
H



1-221
cPr
SO2Me
CF3
H



1-222
CF3
O(CH2)2OMe
F
H



1-223
CF3
O(CH2)3OMe
F
H



1-224
CF3
OCH2CONMe2
F
H



1-225
CF3
[1,4]dioxan-2-yl-
F
H





methoxy





1-226
CF3
O(CH2)2OMe
Cl
H



1-227
CF3
O(CH2)3OMe
Cl
H



1-228
CF3
OCH2CONMe2
Cl
H



1-229
CF3
[1,4]dioxan-2-
Cl
H





ylmethoxy





1-230
CF3
O(CH2)2OMe
Br
H



1-231
CF3
O(CH2)3OMe
Br
H



1-232
CF3
OCH2CONMe2
Br
H



1-233
CF3
[1,4]dioxan-2-
Br
H





ylmethoxy





1-234
CF3
O(CH2)2OMe
I
H



1-235
CF3
O(CH2)3OMe
I
H



1-236
CF3
OCH2CONMe2
I
H



1-237
CF3
[1,4]dioxan-2-
I
H





ylmethoxy





1-238
CF3
F
SO2Me
H



1-239
CF3
F
SO2Et
H



1-240
CF3
O(CH2)2OMe
SO2Me
H



1-241
CF3
O(CH2)2OMe
SO2Et
H



1-242
CF3
O(CH2)3OMe
SO2Me
H



1-243
CF3
O(CH2)3OMe
SO2Et
H



1-244
CF3
OCH2CONMe2
SO2Me
H



1-245
CF3
OCH2CONMe2
SO2Et
H



1-246
CF3
[1,4]dioxan-2-
SO2Me
H





ylmethoxy





1-247
CF3
[1,4]dioxan-2-
SO2Et
H





ylmethoxy





1-248
F
SMe
CF3
H



1-249
F
SOMe
CF3
H



1-250
Cl
Me
SO2Et
H
11.92 (s, 1H), 8.07 (d, 1H),







8.02 (s, 1H), 7.69 (d, 1H),







7.15 (s, 1H), 3.39 (q, 2H),







2.71 (s, 3H), 1.11 (t, 3H)


1-251
Cl
OCH2CHCH2
Cl
H



1-252
Cl
OCH2CHF2
Cl
H



1-253
Cl
O(CH2)2OMe
Cl
H



1-254
Cl
OCH2CONMe2
Cl
H
11.88 (s, 1H), 7.92 (s, 1H),







7.69 (d, 1H), 7.58 (d, 1H),







7.15 (s, 1H), 4.73 (s, 2H),







3.01 (s, 3H), 2.87 (s, 3H)


1-255
Cl
O(CH2)-5-pyrrolidin-2-
Cl
H





one





1-256
Cl
SMe
H
H



1-257
Cl
SOMe
H
H



1-258
Cl
SO2Me
H
H



1-259
Cl
SEt
H
H



1-260
Cl
SOEt
H
H



1-261
Cl
SO2Et
H
H



1-262
Cl
S(CH2)2OMe
H
H



1-263
Cl
SO(CH2)2OMe
H
H



1-264
Cl
SO2(CH2)2OMe
H
H



1-265
Cl
SMe
Me
H



1-266
Cl
SOMe
Me
H



1-267
Cl
SO2Me
Me
H



1-268
Cl
SEt
Me
H



1-269
Cl
SOEt
Me
H



1-270
Cl
SO2Et
Me
H



1-271
Cl
S(CH2)2OMe
Me
H



1-272
Cl
SO(CH2)2OMe
Me
H



1-273
Cl
SO2(CH2)2OMe
Me
H



1-274
Cl
SMe
F
H



1-275
Cl
SOMe
F
H



1-276
Cl
SO2Me
F
H



1-277
Cl
SEt
F
H



1-278
Cl
SOEt
F
H



1-279
Cl
SO2Et
F
H



1-280
Cl
S(CH2)2OMe
F
H



1-281
Cl
SO(CH2)2OMe
F
H



1-282
Cl
SO2(CH2)2OMe
F
H



1-283
Cl
SMe
SO2Me
H
12.02 (s, 1H), 8.09 (d, 1H),







7.93 (s, 1H), 7.86 (d, 1H),







7.17 (s, 1H), 3.57 (s, 3H),







2.52 (s, 3H)


1-284
Cl
SOMe
SO2Me
H
8.22 (d, 1H), 8.10 (d, 1H),







7.95 (s, 1H), 7.19 (s, 1H),







3.54 (s, 3H), 2.50 (s, 3H)


1-285
Cl
SO2Me
SO2Me
H



1-286
Cl
SO2Me
SO2Et
H



1-287
Cl
SEt
SO2Me
H



1-288
Cl
SOEt
SO2Me
H



1-289
Cl
SO2Et
SO2Me
H



1-290
Cl
S(CH2)2OMe
SO2Me
H



1-291
Cl
SO(CH2)2OMe
SO2Me
H



1-292
Cl
SO2(CH2)2OMe
SO2Me
H



1-293
Cl
SMe
CF3
H
12.01 (bs, 1H), 7.92 (s,







1H), 7.89 (d, 1H), 7.86 (d,







1H), 7.18 (s, 1H), 2.09 (s,







3H)


1-294
Cl
SOMe
CF3
H
12.12 (bs, 1H), 8.01-7.92







(m, 3H), 7.18 (s, 1H), 2.50







(s, 3H)


1-295
Cl
SO2Me
CF3
H
12.20 (bs, 1H), 8.16-8.11







(m, 2H), 7.96 (s, 1H), 3.52







(s, 3H)


1-296
Cl
SEt
CF3
H



1-297
Cl
SOEt
CF3
H



1-298
Cl
SO2Et
CF3
H



1-299
Cl
S(CH2)2OMe
CF3
H



1-300
Cl
SO(CH2)2OMe
CF3
H



1-301
Cl
SO2(CH2)2OMe
CF3
H



1-302
Cl
SMe
Br
H



1-303
Cl
SOMe
Br
H



1-304
Cl
SO2Me
Br
H



1-305
Cl
SEt
Br
H



1-306
Cl
SOEt
Br
H



1-307
Cl
SO2Et
Br
H



1-308
Cl
SMe
I
H



1-309
Cl
SOMe
I
H



1-310
Cl
SO2Me
I
H



1-311
Cl
SEt
I
H



1-312
Cl
SOEt
I
H



1-313
Cl
SO2Et
I
H



1-314
Cl
SMe
Cl
H



1-315
Cl
SOMe
Cl
H



1-316
Cl
SO2Me
Cl
H



1-317
Cl
SEt
Cl
H



1-318
Cl
SOEt
Cl
H



1-319
Cl
SO2Et
Cl
H



1-320
Cl
S(CH2)2OMe
Cl
H



1-321
Cl
SO(CH2)2OMe
Cl
H



1-322
Cl
SO2(CH2)2OMe
Cl
H



1-323
Cl
F
SMe
H



1-324
Cl
Cl
SO2Me
H



1-325
Cl
COOMe
SO2Me
H



1-326
Cl
CONMe2
SO2Me
H



1-327
Cl
CONMe(OMe)
SO2Me
H



1-328
Cl
CH2OMe
SO2Me
H



1-329
Cl
CH2OMe
SO2Et
H



1-330
Cl
CH2OEt
SO2Me
H



1-331
Cl
CH2OEt
SO2Et
H



1-332
Cl
CH2OCH2CH2OMe
SO2Me
H



1-333
Cl
CH2OCH2CHF2
SO2Me
H



1-334
Cl
CH2OCH2CF3
SO2Me
H
12.05 (bs, 1H), 8.06 (d,







1H), 7.94-7.89 (m, 2H),







7.18 (s, 1H), 5.24 (s, 2H),







4.28 (q, 2H), 3.35 (s, 3H)


1-335
Cl
CH2OCH2CF3
SO2Et
H



1-336
Cl
CH2OCH2CF2CHF2
SO2Me
H



1-337
Cl
CH2OcPentyl
SO2Me
H



1-338
Cl
CH2PO(OMe)2
SO2Me
H



1-339
Cl
4,5-dihydro-1,2-oxazol-
SMe
H





3-yl





1-340
Cl
4,5-dihydro-1,2-oxazol-
SO2Me
H





3-yl





1-341
Cl
4,5-dihydro-1,2-oxazol-
SO2Et
H





3-yl





1-342
Cl
5-cyanomethyl-4,5-
SO2Me
H





dihydro-1,2-oxazol-3-yl





1-343
Cl
5-cyanomethyl-4,5-
SO2Et
H





dihydro-1,2-oxazol-3-yl





1-344
Cl
5-(methoxymethyl)-4,5-
SO2Et
H





dihydro-1,2-oxazol-3-yl





1-345
Cl
5-(methoxymethyl)-5-
SO2Et
H





methyl-4,5-dihydro-







1,2-oxazol-3-yl





1-346
Cl
CH2O-tetrahydrofuran-
SO2Me
H





3-yl





1-347
Cl
CH2O-tetrahydrofuran-
SO2Et
H





3-yl





1-348
Cl
CH2OCH2-
SO2Me
H





tetrahydrofuran-2-yl





1-349
Cl
CH2OCH2-
SO2Et
H





tetrahydrofuran-2-yl





1-350
Cl
CH2OCH2-
SO2Me
H





tetrahydrofuran-3-yl





1-351
Cl
CH2OCH2-
SO2Et
H





tetrahydrofuran-3-yl





1-352
Cl
OMe
SO2Me
H



1-353
Cl
OMe
SO2Et
H



1-354
Cl
OEt
SO2Me
H



1-355
Cl
OEt
SO2Et
H



1-356
Cl
OiPr
SO2Me
H



1-357
Cl
OiPr
SO2Et
H



1-358
Cl
OnPr
SO2Me
H



1-359
Cl
O(CH2)2F
SO2Me
H



1-360
Cl
O(CH2)2OMe
SO2Me
H



1-361
Cl
O(CH2)4OMe
SO2Me
H



1-362
Cl
O(CH2)4OMe
SO2Et
H



1-363
Cl
O(CH2)3OMe
SO2Me
H



1-364
Cl
O(CH2)3OMe
SO2Et
H



1-365
Cl
O(CH2)2OMe
SO2Me
H



1-366
Cl
O(CH2)2OMe
SO2Et
H



1-367
Cl
OCH2-c-Pr
SO2Et
H



1-368
Cl
[1,4]dioxan-2-yl-
SO2Me
H





methoxy





1-369
Cl
[1,4]dioxan-2-yl-
SO2Et
H





methoxy





1-370
Cl
OCH2(CO)NMe2
SO2Me
H



1-371
Cl
OCH2(CO)NMe2
SO2Et
H



1-372
Br
OMe
Br
H



1-373
Br
O(CH2)2OMe
Br
H



1-374
Br
O(CH2)2OMe
SO2Me
H



1-375
Br
O(CH2)2OMe
SO2Et
H



1-376
Br
O(CH2)3OMe
SO2Me
H



1-377
Br
O(CH2)3OMe
SO2Et
H



1-378
Br
O(CH2)4OMe
SO2Me
H



1-379
Br
O(CH2)4OMe
SO2Et
H



1-380
Br
[1,4]dioxan-2-
SO2Me
H





ylmethoxy





1-381
Br
[1,4]dioxan-2-
SO2Et
H





ylmethoxy





1-382
I
O(CH2)2OMe
SO2Me
H



1-383
I
O(CH2)2OMe
SO2Et
H



1-384
I
O(CH2)3OMe
SO2Me
H



1-385
I
O(CH2)3OMe
SO2Et
H



1-386
I
O(CH2)4OMe
SO2Me
H



1-387
I
O(CH2)4OMe
SO2Et
H



1-388
I
[1,4]dioxan-2-
SO2Me
H





ylmethoxy





1-389
I
[1,4]dioxan-2-
SO2Et
H





ylmethoxy





1-390
OMe
SMe
CF3
H



1-391
OMe
SOMe
CF3
H



1-392
OMe
SO2Me
CF3
H



1-393
OMe
SEt
CF3
H



1-394
OMe
SOEt
CF3
H



1-395
OMe
SO2Et
CF3
H



1-396
OMe
S(CH2)2OMe
CF3
H



1-397
OMe
SO(CH2)2OMe
CF3
H



1-398
OMe
SO2(CH2)2OMe
CF3
H



1-399
OMe
SMe
CHF2
H



1-400
OMe
SOMe
CHF2
H



1-401
OMe
SO2Me
CHF2
H



1-402
OMe
SEt
CHF2
H



1-403
OMe
SOEt
CHF2
H



1-404
OMe
SO2Et
CHF2
H



1-405
OMe
S(CH2)2OMe
CHF2
H



1-406
OMe
SO(CH2)2OMe
CHF2
H



1-407
OMe
SO2(CH2)2OMe
CHF2
H



1-408
OMe
SMe
Cl
H



1-409
OMe
SOMe
Cl
H



1-410
OMe
SO2Me
Cl
H



1-411
OMe
SEt
Cl
H



1-412
OMe
SOEt
Cl
H



1-413
OMe
SO2Et
Cl
H



1-414
OMe
S(CH2)2OMe
Cl
H



1-415
OMe
SO(CH2)2OMe
Cl
H



1-416
OMe
SO2(CH2)2OMe
Cl
H



1-417
OEt
SMe
CF3
H



1-418
OEt
SOMe
CF3
H



1-419
OEt
SO2Me
CF3
H



1-420
OEt
SEt
CF3
H



1-421
OEt
SOEt
CF3
H



1-422
OEt
SO2Et
CF3
H



1-423
OEt
S(CH2)2OMe
CF3
H



1-424
OEt
SO(CH2)2OMe
CF3
H



1-425
OEt
SO2(CH2)2OMe
CF3
H



1-426
OEt
SMe
CHF2
H



1-427
OEt
SOMe
CHF2
H



1-428
OEt
SO2Me
CHF2
H



1-429
OEt
SEt
CHF2
H



1-430
OEt
SOEt
CHF2
H



1-431
OEt
SO2Et
CHF2
H



1-432
OEt
S(CH2)2OMe
CHF2
H



1-433
OEt
SO(CH2)2OMe
CHF2
H



1-434
OEt
SO2(CH2)2OMe
CHF2
H



1-435
OEt
SMe
Cl
H



1-436
OEt
SOMe
Cl
H



1-437
OEt
SO2Me
Cl
H



1-438
OEt
SEt
Cl
H



1-439
OEt
SOEt
Cl
H



1-440
OEt
SO2Et
Cl
H



1-441
OEt
S(CH2)2OMe
Cl
H



1-442
OEt
SO(CH2)2OMe
Cl
H



1-443
OEt
SO2(CH2)2OMe
Cl
H



1-444
O(CH2)2c-Pr
SMe
CF3
H



1-445
O(CH2)2c-Pr
SOMe
CF3
H



1-446
O(CH2)2c-Pr
SO2Me
CF3
H



1-447
O(CH2)2c-Pr
SEt
CF3
H



1-448
O(CH2)2c-Pr
SOEt
CF3
H



1-449
O(CH2)2c-Pr
SO2Et
CF3
H



1-450
O(CH2)2c-Pr
S(CH2)2OMe
CF3
H



1-451
O(CH2)2c-Pr
SO(CH2)2OMe
CF3
H



1-452
O(CH2)2c-Pr
SO2(CH2)2OMe
CF3
H



1-453
O(CH2)2c-Pr
SMe
Cl
H



1-454
O(CH2)2c-Pr
SOMe
Cl
H



1-455
O(CH2)2c-Pr
SO2Me
Cl
H



1-456
O(CH2)2c-Pr
SEt
Cl
H



1-457
O(CH2)2c-Pr
SOEt
Cl
H



1-458
O(CH2)2c-Pr
SO2Et
Cl
H



1-459
O(CH2)2c-Pr
S(CH2)2OMe
Cl
H



1-460
O(CH2)2c-Pr
SO(CH2)2OMe
Cl
H



1-461
O(CH2)2c-Pr
SO2(CH2)2OMe
Cl
H



1-462
O(CH2)2c-Pr
SMe
SO2Me
H



1-463
O(CH2)2c-Pr
SOMe
SO2Me
H



1-464
O(CH2)2c-Pr
SO2Me
SO2Me
H



1-465
O(CH2)2c-Pr
SEt
SO2Me
H



1-466
O(CH2)2c-Pr
SOEt
SO2Me
H



1-467
O(CH2)2c-Pr
SO2Et
SO2Me
H



1-468
O(CH2)2c-Pr
S(CH2)2OMe
SO2Me
H



1-469
O(CH2)2c-Pr
SO(CH2)2OMe
SO2Me
H



1-470
O(CH2)2c-Pr
SO2(CH2)2OMe
SO2Me
H



1-471
SO2Me
F
CF3
H



1-472
SO2Me
NH2
CF3
H



1-473
SO2Me
NHEt
Cl
H



1-474
SMe
SEt
F
H



1-475
SMe
SMe
F
H



1-476
Me
NH2
Cl
H



1-477
Me
NHMe
Cl
H



1-478
Me
NMe2
Cl
H



1-479
Me
pyrazol-1-yl
Cl
H



1-480
Me
NH2
Br
H



1-481
Me
NHMe
Br
H



1-482
Me
NMe2
Br
H



1-483
Me
NH2
SO2Me
H



1-484
Me
NHMe
SO2Me
H



1-485
Me
NMe2
SO2Me
H



1-486
Me
NH(CH2)2OMe
SO2Me
H



1-487
Me
morpholin-4-yl
SO2Me
H



1-488
Me
1,2,3-triazol-1-yl
SO2Me
H



1-489
Me
1,2,3-triazol-2-yl
SO2Me
H



1-490
Me
pyrazol-1-yl
SO2Me
H



1-491
Me
1,2,4-triazol-1-yl
SO2Me
H



1-492
Me
NH2
CF3
H



1-493
Me
NHMe
CF3
H



1-494
Me
NMe2
CF3
H



1-495
Me
NH(CH2)2OMe
CF3
H



1-496
Me
morpholin-4-yl
CF3
H



1-497
Me
1,2,3-triazol-1-yl
CF3
H



1-498
Me
1,2,3-triazol-2-yl
CF3
H



1-499
Me
pyrazol-1-yl
CF3
H



1-500
Me
1,2,4-triazol-1-yl
CF3
H



1-501
Cl
NH2
Cl
H



1-502
Cl
NHMe
Cl
H



1-503
Cl
NMe2
Cl
H



1-504
Cl
pyrazol-1-yl
Cl
H



1-505
Cl
NH2
Br
H



1-506
Cl
NHMe
Br
H



1-507
Cl
NMe2
Br
H



1-508
Cl
NH2
SO2Me
H



1-509
Cl
NHMe
SO2Me
H



1-510
Cl
NMe2
SO2Me
H



1-511
Cl
NH(CH2)2OMe
SO2Me
H



1-512
Cl
morpholin-4-yl
SO2Me
H



1-513
Cl
1,2,3-triazol-1-yl
SO2Me
H



1-514
Cl
1,2,3-triazol-2-yl
SO2Me
H



1-515
Cl
pyrazol-1-yl
SO2Me
H



1-516
Cl
1,2,4-triazol-1-yl
SO2Me
H



1-517
Cl
NH2
CF3
H



1-518
Cl
NHMe
CF3
H



1-519
Cl
NMe2
CF3
H



1-520
Cl
NH(CH2)2OMe
CF3
H



1-521
Cl
morpholin-4-yl
CF3
H



1-522
Cl
1,2,3-triazol-1-yl
CF3
H



1-523
Cl
1,2,3-triazol-2-yl
CF3
H



1-524
Cl
pyrazol-1-yl
CF3
H



1-525
Cl
1,2,4-triazol-1-yl
CF3
H



1-526
Cl
sulfoximine 1
Cl
H



1-527
Cl
sulfoximine 2
Cl
H



1-528
Cl
sulfoximine 3
Cl
H



1-529
Cl
sulfoximine 4
Cl
H



1-530
Cl
sulfoximine 5
Cl
H



1-531
Cl
sulfoximine 3
OMe
H



1-532
Cl
sulfoximine 4
OMe
H



1-533
Cl
sulfoximine 5
OMe
H



1-534
Cl
sulfoximine 3
COOMe
H



1-535
Cl
sulfoximine 4
COOMe
H



1-536
Cl
sulfoximine 5
COOMe
H



1-537
OMe
sulfoximine 3
OMe
H



1-538
OMe
sulfoximine 4
OMe
H



1-539
OMe
sulfoximine 5
OMe
H



1-540
Me
sulfoximine 1
CF3
H



1-541
Me
sulfoximine 2
CF3
H



1-542
Me
sulfoximine 1
SO2Me
H



1-543
Me
sulfoximine 2
SO2Me
H



1-544
Me
sulfoximine 1
Cl
H



1-545
Me
sulfoximine 2
Cl
H
















TABLE 2







Compounds of the general formula (I) according to the invention in which


R represents methyl and R′ represents hydrogen, A represents C-Y, and


V, X, Y and Z have the meanings given in Table 1.








 

















Physical data


No.
X
Y
Z
V
(1H-NMR, DMSO-d6, 400 MHz)





2-173
Me
SO2Me
CF3
H
11.82 (s, 1H), 8.00 (d, 1H), 7.93







(d, 1H), 7.63 (s, 1H), 3.41 (s,







3H), 2.70 (s, 3H), 2.07 (s, 3H)
















TABLE 3





Compounds of the general formula (I) according to the invention in which


R represents ethyl and R′ represents hydrogen, A represents C—Y, 


and V, X, Y and Z have the meanings given in Table 1.



























TABLE 4





Compounds of the general formula (I) according to the invention in which


R represents phenyl and R′ represents hydrogen, A represents C—Y, 


and V, X, Y and Z have the meanings given in Table 1.



























TABLE 5







Compounds of the general formula (I) according to the invention in which


R represents benzyl and R′ represents hydrogen, A represents C—Y, 


and V, X, Y and Z have the meanings given in Table 1.








 

















Physical data


No.
X
Y
Z
V
(1H-NMR, DMSO-d6, 400 MHz)





5-163
Me
SO2Me
SO2Me
H
11.81 (s, 1H), 8.19 (d, 1H), 7.97







(d, 1H), 7.34-7.25 (m, 5H), 6.66







(s, 1H), 4.02 (s, 2H), 3.58 (s,







3H), 3.54 (s, 3H), 2.66 (s, 3H)


5-173
Me
SO2Me
CF3
H
11.79 (bs, 1H), 8.01 (d, 1H),







7.97 (d, 1H), 7.34-7.25 (m, 5H),







6.64 (s, 1H), 4.02 (s, 2H), 3.39







(s, 3H), 2.71 (s, 3H)
















TABLE 6







Compounds of the general formula (I) according to the invention in 


which R represents trifluoromethyl and R′ represents hydrogen, A 


represents C—Y, and V, X, Y and Z have the meanings given in Table 1.








 

















Physical data


No.
X
Y
Z
V
(1H-NMR, DMSO-d6, 400 MHz)





6-173
Me
SO2Me
CF3
H
7.92 (d, 1H), 7.85 (d, 1H), 7.26 







(s, 1H), 3.26 (s, 3H), 2.87 (s, 3H),
















TABLE 7







Compounds of the general formula (I) according to the invention in 


which R represents hydrogen and R′ represents methyl, A represents 


C—Y, and V, X, Y and Z have the meanings given in Table 1.








 

















Physical data







(1H-NMR, 


No.
X
Y
Z
V
DMSO-d6, 400 MHz)





7-13 
Cl
H
SO2Me
H
11.89 (s, 1H), 8.11 (s, 1H), 







7.99 (d, 1H), 7.88 (d, 1H), 







7.61 (d, 1H) 3.33 (s, 3H), 







2.07 (s, 3H)


7-334
Cl
CH2OCH2CF3
SO2Me
H
12.94 (s, 1H), 8.09 (d, 1H), 







7.88 (d, 1H), 7.62 (s, 1H), 







5.24 (s, 2H), 4.28 (q, 2H), 







3.36 (s, 3H), 2.08 (s, 3H)
















TABLE 8







Compounds of the general formula (I) according 


to the invention in which R represents hydrogen, R′ 


represents trifluoromethyl and A represents C—Y, and 


V, X, Y and Z have the meanings given in Table 1.








 

















Physical data







(1H-NMR, 


No.
X
Y
Z
V
DMSO-d6, 400 MHz)





8-13 
Cl
H
SO2Me
H
12.52 (s, 1H), 8.75 (s, 1H), 







8.13 (d, 1H), 8.01 (d, 1H), 







7.95 (d, 1H) 3.33 (s, 3H)


8-29 
CF3
H
SO2Me
H
12.65 (s, 1H), 8.75 (s, 1H), 







8.37-8.22 (m, 2H), 8.08 (d, 







1H), 3.34 (s, 3H)


8-32 
NO2
H
NO2
H
12.75 (s, 1H), 8.89 (s, 1H), 







8.81-8.65 (m, 2H), 8.13 (d, 







1H),


8-37 
NO2
H
F
H
12.79 (s, 1H), 8.89 (s, 1H), 







8.80-8.67 (m, 2H), 8.13 (d, 







1H),


8-38 
NO2
H
Cl
H
12.51 (s, 1H), 8.71 (s, 1H), 







8.31 (d, 1H), 8.01 (dd, 1H), 







7.87 (d, 1H)


8-39 
NO2
H
Br
H
12.50 (s, 1H), 8.71 (s, 1H), 







8.41 (d, 1H), 8.14 (dd, 1H), 







7.78 (d, 1H)


8-42 
NO2
H
SO2Me
H
12.67 (s, 1H), 8.74 (s, 1H), 







8.66 (d, 1H), 8.44 (dd, 1H), 







8.12 (d, 1H), 3.42 (s, 3H)


8-44 
NO2
H
CF3
H
12.62 (s, 1H), 8.72 (s, 1H), 







8.55 (s, 1H), 7.33 (d, 1H), 







8.06 (d, 1H)


8-172
Me
SOMe
CF3
H
13.38 (s, 1H), 8.73 (s, 1H), 







7.87-7.82 (m, 2H), 3.06 (s, 







3H), 2.83 (s, 3H)


8-173
Me
SO2Me
CF3
H
12.43 (s, 1H), 8.73 (s, 1H), 







8.03 (d, 1H), 7.98 (d, 1H), 







3.42 (s, 3H), 2.72 (s, 3H)


8-249
F
SOMe
CF3
H



8-334
Cl
CH2OCH2CF3
SO2Me
H
12.60 (s, 1H), 8.74 (s, 1H), 







8.11 (d, 1H), 7.95 (d, 1H), 







5.25 (s, 2H), 4.30 (q, 2H), 







3.36 (s, 3H)


8-343
Cl
5-cyanomethyl-
SO2Et
H
12.60 (s, 1H), 8.73 (s, 1H), 




4,5-dihydro- 


8.11 (d, 1H), 8.07 (d, 1H), 




1,2-oxazol-3 yl


5.19 (m, 1H), 3.66-3.54 (m, 







1H), 3.25-3.49 (m, 5H), 3.17 







(dd, 1H), 3.09-2.95 (m, 2H), 







1.15 (t, 3H)


8-348
Cl
CH2OCH2-
SO2Me

12.54 (s, 1H), 8.73 (s, 1H), 




tetrahydrofuran-


8.00 (d, 1H), 7.89 (d, 1H), 




2-yl


5.08 (s, 2H), 3.97 (m, 1H), 







3.70 (dd, 1H), 3.65-3.51 (m, 







3H), 3.40 (s, 3H), 1.93-1.70 







(m, 3H), 1.58-1.49 (m, 1H).
















TABLE 9







Compounds of the general formula (I) according 


to the invention in which R represents hydrogen, R′ 


represents phenyl and A represents C—Y, and 


V, X, Y and Z have the meanings given in Table 1.








 

















Physical data







(1H-NMR, 


No.
X
Y
Z
V
DMSO-d6, 400 MHz)





9-13 
Cl
H
SO2Me
H
8.87 (s, 1H), 8.11 (s, 1H), 8.04 







(d, 1H), 8.00 (d, 1H), 7.87 (m, 







2H), 7.49 (m, 3H), 6.92 (s, 







1H), 3.12 (s, 3H)


9-334
Cl
CH2OCH2CF3
SO2Me
H
8.99 (s, 1H), 8.17 (d, 1H), 







7.89-7.80 (m, 3H), 7.49 (m, 







3H), 6.91 (s, 1H), 5.38 (s, 2H), 







4.08 (q, 2H), 3.20 (s, 3H)
















TABLE 10







Compounds of the general formula (I) 


according to the invention in which A represents N








 



















Physical data








(1H-NMR, 








DMSO-d6, 


No.
R
R′
X
Z
V
400 MHz)





10-1 
H
H
Cl
CF3
H
8.34 (d, 1H), 7.71 








(d, 1H), 7.41 (s, 








1H), 6.92 (s, 1H)


10-2 
H
H
Me
CF3
H
8.22 (d, 1H), 7.94 








(s, 1H), 7.86 (d, 








1H), 7.18 (s, 1H, 








2.65 (s, 3H))


10-3 
H
H
CH2OMe
CF3
H



10-4 
H
H
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)-








methyl





10-5 
H
H
CH2OCH2CH2OMe
CF3
H



10-6 
H
H






10-7 
H
Me
Cl
CF3
H



10-8 
H
Me
Me
CF3
H



10-9 
H
Me
CH2OMe
CF3
H



10-10
H
Me
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)-








methyl





10-11
H
Me
CH2OCH2CH2OMe
CF3
H



10-12
H
Me






10-13
H
Et
Cl
CF3
H



10-14
H
Et
Me
CF3
H



10-15
H
Et
CH2OMe
CF3
H



10-16
H
Et
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)-








methyl





10-17
H
Et
CH2OCH2CH2OMe
CF3
H



10-18
H
Et






10-19
H
CF3
Cl
CF3
H



10-20
H
CF3
Me
CF3
H



10-21
H
CF3
CH2OMe
CF3
H



10-22
H
CF3
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)- 








methyl





10-23
H
CF3
CH2OCH2CH2OMe
CF3
H



10-24
H
CF3






10-25
H
Ph
Cl
CF3
H
9.32 (bs, 1H), 8.43 








(d, 1H), 7.88-7.69 








(m, 3H), 7.51-7.47 








(m, 3H), 6.90 (s, 








1H)


10-26
H
Ph
Me
CF3
H



10-27
H
Ph
CH2OMe
CF3
H



10-28
H
Ph
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)-








methyl





10-29
H
Ph
CH2OCH2CH2OMe
CF3
H



10-30
H
Ph






10-31
Me
H
Cl
CF3
H



10-32
Me
H
Me
CF3
H



10-33
Me
H
CH2OMe
CF3
H



10-34
Me
H
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)-








methyl





10-35
Me
H
CH2OCH2CH2OMe
CF3
H



10-36
Me
H






10-37
Et
H
Cl
CF3
H



10-38
Et
H
Me
CF3
H



10-39
Et
H
CH2OMe
CF3
H



10-40
Et
H
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)-








methyl





10-41
Et
H
CH2OCH2CH2OMe
CF3
H



10-42
Et
H






10-43
CF3
H
Cl
CF3
H



10-44
CF3
H
Me
CF3
H



10-45
CF3
H
CH2OMe
CF3
H



10-46
CF3
H
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)-








methyl





10-47
CF3
H
CH2OCH2CH2OMe
CF3
H



10-48
CF3
H






10-49
Ph
H
Cl
CF3
H



10-50
Ph
H
Me
CF3
H



10-51
Ph
H
CH2OMe
CF3
H



10-52
Ph
H
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)-








methyl





10-53
Ph
H
CH2OCH2CH2OMe
CF3
H



10-54
Ph
H






10-55
Me
Me
Cl
CF3
H
8.48 (d, 1H), 7.64 








(d, 1H), 2.22 (s, 








3H), 2.12 (s, 3H)


10-56
Me
Me
Me
CF3
H



10-57
Me
Me
CH2OMe
CF3
H



10-58
Me
Me
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)-








methyl





10-59
Me
Me
CH2OCH2CH2OMe
CF3
H



10-60
Me
Me






10-61
Ph
Ph
Cl
CF3
H



10-62
Ph
Ph
Me
CF3
H



10-63
Ph
Ph
CH2OMe
CF3
H



10-64
Ph
Ph
(1,1-dioxido-1,2-
CF3
H






thiadiazolidin-1-yl)-








methyl





10-65
Ph
Ph
CH2OCH2CH2OMe
CF3
H



10-66
Ph
Ph
















TABLE 11







Compounds of the general formula (I) according to the


invention in which R and R′ represent methyl and A represents 


C—Y, and V, X, Y and Z have the meanings given in Table 1.








 

















Physical data







(1H-NMR, 


No.
X
Y
Z
V
DMSO-d6, 400 MHz)





11-13 
Cl
H
SO2Me
H
11.48 (s, 1H), 8.02-7.97 







(m, 2H), 7.86 (d, 1H), 







3.07 (s, 3H), 2.24 (s, 







3H), 2.11 (s, 3H)


11-29 
SO2Me

CF3
H
11.89 (s, 1H), 8.30-8.14 







(m, 2H), 7.92 (d, 1H), 







3.50 (s, 3H), 2.20 (s, 







3H), 2.02 (s, 3H)


11-173
Cl
SO2Me
CF3
H
7.98 (d, 1H), 7.90 (d, 







1H), 3.37 (s, 3H), 







2.70 (s, 3H), 2.22 (s, 







3H), 2.01 (s, 3H)


11-334
Cl
CH2OCH2CF3
SO2Me
H
8.11 (d, 1H), 7.83 (d, 







1H), 5.39 (s, 2H), 







4.02 (q, 2H), 3.20 (s, 







3H), 2.24 (s, 3H), 2.13 







(s, 3H)


11-343
Cl
5-cyanomethyl- 
SO2Et
H
8.11 (d, 1H), 8.07 (d, 




4,5-dihydro-1,2-


1H), 5.18 (m, 1H), 




oxazol-3 yl


3.62-3.54 (m, 1H), 







3.25-3.49 (m, 2H), 







3.17 (dd, 1H), 3.09-







2.96 (m, 2H), 2.21 (s, 







3H), 2.01 (s, 3H), 1.15 







(t, 3H)









B. Formulation Examples

    a) A dusting product is obtained by mixing 10 parts by weight of a compound of the formula (I) and/or salts thereof and 90 parts by weight of talc as an inert substance and comminuting the mixture in a hammer mill.
    b) A readily water-dispersible wettable powder is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill.
    c) A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I) and/or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example about 255 to above 277° C.) and grinding the mixture in a friction ball mill to a fineness of below 5 microns.
    d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and/or salts thereof, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.
    e) Water-dispersible granules are obtained by mixing
    
        75 parts by weight of a compound of the formula (I) and/or salts thereof,
        10 parts by weight of calcium lignosulfonate,
        5 parts by weight of sodium laurylsulfate,
        3 parts by weight of polyvinyl alcohol and
        7 parts by weight of kaolin,
        grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid.
    
    
    f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,
    
        25 parts by weight of a compound of the formula (I) and/or salts thereof,
        5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,
        2 parts by weight of sodium oleoylmethyltaurate,
        1 part by weight of polyvinyl alcohol,
        17 parts by weight of calcium carbonate and
        50 parts by weight of water,
        then grinding the mixture in a bead mill and atomizing and drying the suspension thus obtained in a spray tower by means of a one-phase nozzle.

C. Biological Examples

    
    


1. Pre-emergence Herbicidal Action Against Harmful Plants
Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in wood-fiber pots in sandy loam and covered with soil. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the soil cover in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 l/ha, with addition of 0.2% wetting agent. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the test plants. The damage to the test plants is assessed visually after a test period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Here, for example, compounds No. 1-163, 1-171, 1-172, 1-283, 1-284, 1-294, 1-295, 1-334, 10-001 and 11-343, at an application rate of 320 g/ha, have an activity of at least 80% against Veronica persica.
2. Post-emergence Herbicidal Action Against Harmful Plants
Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in wood fiber pots in sandy loam, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plants in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 l/ha, with addition of 0.2% wetting agent. After the test plants have been left to stand in the greenhouse under optimal growth conditions for about 3 weeks, the action of the preparations is assessed visually in comparison to untreated controls (herbicidal action in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Here, for example, compounds No. 1-163, 1-171, 1-172, 1-173, 1-254, 1-283, 1-284, 1-293, 1-294 and 1-334, at an application rate of 80 g/ha, have an activity of at least 80% against Abutilon theophrasti and Amaranthus retroflexus.
3. Comparative Tests
In the tables below, the properties of the compounds according to the invention are compared to those of the structurally most similar compounds known from WO 2012/028579 A1. These tests were carried out by the pre- and post-emergence method under the conditions mentioned under item 1 and item 2. Here, the herbicidal activity against various harmful plants and the damage of some important crop plants were compared at different dosages.
The abbreviations used denote:
Harmful Plants
ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AMARE Amaranthus retroflexus AVEFA Avena fatua CYPES Cyperus serotinus ECHCG Echinochloa crus galli LOLMU Lolium multiflorum MATIN Matricaria inodora PHBPU Pharbitis purpureum POLCO Polygonum convolvulus SETVI Setaria viridis STEME Stellaria media VERPE Veronica persica
Crop Plants
BRSNW Brassica napus (Oilseed Rape) ORYZA Oryza sativa (Rice) ZEAMX Zea mays (Corn) TRZAS Triticum aestivum (Wheat)
3a. Tables A to L: Pre-emergence Action







TABLE A







Dosage 80/ha, damage of crop plants










Compound
ORYZA
TRZAS
BRSNW








   according to the invention, No. 1-171
 0%
 0%
30%


 





   WO 2012/028579, No. 4-135
60%
60%
80%
















TABLE B







Dosage 80/ha, damage of crop plants










Compound
ORYZA
TRZAS
BRSNW








   according to the invention, No. 1-171
 0%
 0%
30%


 





   WO 2012/028579, No. 5-146
90%
30%
90%
















TABLE C







Dosage 320/ha, herbicidal activity against harmful plants











Compound
ECHCG
ABUTH
AMARE
MATIN








   according to the invention, No. 1-163
70%
100%
90%
100%


 





   WO 2012/028579, No. 1-188
 0%
 0%
40%
 40%
















TABLE D







Dosage 320/ha, herbicidal activity against 


harmful plants and damage of crop plants











Harmful 



Crop plant
plant


Compound
BRSNW
ALOMY








   according to the invention, No. 1-163
10%
30%


 





   WO 2012/028579, No. 6-189
90%
 0%
















TABLE E







Dosage 320/ha, herbicidal activity against harmful plants and damage of crop plants










Crop plant
Harmful plant











Compound
ORYZA
TRZAS
LOLMU
POLCO








   according to the invention, No. 1-163
 0%
 0%
100%
70%


 





   WO 2012/028579, No. 6-189
80%
30%
 70%
 0%
















TABLE F







Dosage 320/ha, herbicidal activity against harmful plants









Compound
LOLMU
POLCO








   according to the invention, No. 1-284
100%
70%


 





   WO 2012/028579, No. 4-293
 20%
20%
















TABLE G







Dosage 320/ha, damage of crop plants










Compound
ORYZA
ZEAMX
BRSNW








   according to the invention, No. 1-294
30%
 0%
20%


 





   WO 2012/028579, No. 4-639
90%
40%
90%
















TABLE H







Dosage 80/ha, herbicidal activity against harmful plants











Compound
ECGCG
MATIN










   according to the invention, No. 10-1
70%
90%



 






   WO 2012/028579, No. 8-9
 0% 
60%

















TABLE I







Damage of ORYZA at different dosages











Compound
80 g/ha
20 g/ha










   according to the invention, No. 10-1
 0%
 0%



 






   WO 2012/028579, No. 8-10
90%
50%

















TABLE J







Herbicidal activity against AVEFA at different dosages










320 
80 


Compound
g/ha
g/ha








   according to the invention, No. 11-343
100%
80%


 





   WO 2012/028579, No. 1-267
0%
0%
















TABLE K







Herbicidal activity against AVEFA at different dosages










80 
20 


Compound
g/ha
g/ha








   according to the invention, No. 11-343
80%
80%


 





   WO 2012/028579, No. 4-268
0%
0%
















TABLE L







Herbicidal activity against AVEFA at different dosages










80 
20 


Compound
g/ha
g/ha








   according to the invention, No. 11-343
80%
80%


 





   WO 2012/028579, No. 6-268
0%
0%









3b. Tables M to X: Post-emergence Action








TABLE M







Dosage 80/ha, damage of crop plants










Compound
ORYZA
TRZAS
BRSNW








   according to the invention, No. 1-171
0%
0%
0%


 





   WO 2012/028579, No. 4-135
100%
100%
100%
















TABLE N







Dosage 80/ha, damage of crop plants










Compound
ORYZA
TRZAS
BRSNW








   according to the invention, No. 1-171
0%
0%
0%


 





   WO 2012/028579, No. 5-146
80%
60%
100%
















TABLE O







Dosage 20/ha, damage of crop plants










Compound
ORYZA
TRZAS
BRSNW








   according to the invention, No. 1-163
0%
20%
40%


 





   WO 2012/028579, No. 1-188
20%
40%
100%
















TABLE P







Dosage 80/ha, herbicidal activity against harmful plants











Compound
ALOMY
AVEFA
LOMU
SETVI








   according to the invention, No. 1-163
60%
40%
20%
100%


 





   WO 2012/028579, No. 6-189
0%
0%
0%
20%
















TABLE Q







Dosage 80/ha, herbicidal activity against harmful plants and damage 


of crop plants










Crop




plant
Harmful plants










Compound
ORYZA
CYPES
LOLMU








   according to the invention, No. 1-284
20%
60%
70%


 





   WO 2012/028579, No. 4-293
40%
40%
40%
















TABLE R







Dosage 20/ha, herbicidal activity against harmful plants









Compound
LOLMU
SETVI








   according to the invention, No. 1-284
60%
90%


 





   WO 2012/028579, No. 5-294
10%
0%
















TABLE S







Dosage 20/ha, herbicidal activity against harmful plants and damage of crop plants










Crop plants
Harmful plant











Compound
ORYZA
TRZAS
ZEAMX
PHBPU








   according to the invention, No. 1-294
0%
0%
0%
70%


 





   WO 2012/028579, No. 4-639
60%
100%
80%
40%
















TABLE T







Dosage 5/ha, herbicidal activity against harmful plants











Compound
STEME
VERPE










   according to the invention, No. 10-1
40%
90%



 






   WO 2012/028579, No. 8-9
10%
60%

















TABLE U







Dosage 80 g/ha, damage of crop plants











Compound
ORYZA
ZEAMX










   according to the invention, No. 10-1
0%
0%



 






   WO 2012/028579, No. 8-10
90%
90%

















TABLE V







Damage of BRSNW at different dosages









Compound 
80 g/ha
20 g/ha








   according to the invention, No. 11-343
0%
0%


 





   WO 2012/028579, No. 1-267
90%
90%
















TABLE W







Damage of BRSNW at different dosages









Compound
20 g/ha
5 g/ha








   according to the invention, No. 11-343
0%
0%


 





   WO 2012/028579, No. 4-268
100%
80%
















TABLE X







Damage of BRSNW at different dosages









Compound
80 g/ha
20 g/ha








   according to the invention, No. 11-343
0%
0%


 





   WO 2012/028579, No. 6-268
60%
20%

## Claims

1. An N-(oxazol-2-yl)arylcarboxamide of formula (I) and/or a salt thereof



in which
A represents CY,
X represents nitro, halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, OR2, S(O)nR2, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, or (C1-C6)-alkyl-NR1SO2R2,
Y represents hydrogen, nitro, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, OR1, S(O)nR2, SO2N(R1)2, N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, or (C1-C6)-alkylphenyl, where the (C1-C6)-alkylphenyl radical is substituted by s radicals selected from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C4)-alkyl and cyanomethyl,
Z represents halogen, cyano, nitro, (C1-C6)-alkoxy, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, or S(O)nR2, or Z optionally represents hydrogen if Y represents S(O)nR2,
V represents hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-halo-alkoxy, S(O)n—(C1-C6)-alkyl, S(O)n—(C1-C6)-haloalkyl, (C1-C6)-alkoxy-(C1-C4)-alkyl, halogen, nitro or cyano,
R and R′ independently of one another each represent hydrogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, cyano-(C1-C6)-alkyl, cyano, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, halogen, amino, or methoxymethyl, with the proviso that at least one of R and/or R′ is hydrogen,
R1 represents hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, phenyl, or phenyl-(C1-C6)-alkyl, where the radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, NR3COR3, NR3SO2R4, CO2R3, CON(R3)2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl,
R2 represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl that are each substituted by s radicals from the group consisting of halogen and OR3,
R3 represents hydrogen or (C1-C6)-alkyl,
R4 represents (C1-C6)-alkyl,
n represents 0, 1 or 2, and
s represents 0, 1, 2 or 3.

2. A herbicidal composition comprising a herbicidally active content of at least one compound of the formula (I) and/or salt as claimed in claim 1 and one or more formulation auxiliaries.

3. A method for controlling unwanted plants, comprising applying an effective amount of at least one compound of formula (I) and/or salt as claimed in claim 1 to the plants and/or to a site of unwanted plants.

4. A method as claimed in claim 3, comprising controlling one or more unwanted plants in crops of useful plants.

5. A method as claimed in claim 4, wherein the useful plants are transgenic useful plants.

6. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which Y is other than hydrogen.

7. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which V is other than hydrogen.

8. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which one of R and/or R′ is other than hydrogen.

9. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which one of R and/or R′ is other than hydrogen or (C1-C6)-alkyl.

10. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which X is other than (C1-C6)-alkyl.

11. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which Y is other than (C1-C6)-alkyl.

12. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which R, R′ and V are hydrogen.

13. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which one of R and R′ is hydrogen and the other is not hydrogen, and V is hydrogen.

14. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which
A represents CY,
X represents nitro, halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (OR2, S(O)nR2, (C1-C6)-alkyl-S(O)nR2, or (C1-C6)-alkyl-OR1,
Y represents hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, OR1, S(O)nR2, N(R1)2, or (C1-C6)-alkyl-OR1,
Z represents halogen, cyano, nitro, (C1-C6)-alkoxy, halo-(C1-C6)-alkyl, or S(O)nR2, or Z optionally represents hydrogen if Y represents S(O)nR2,
V represents hydrogen or halogen,
R and R′ independently of one another each represent hydrogen or (C1-C6)-alkyl, with the proviso that at least one of R and/or R′ is hydrogen,
R1 represents hydrogen, (C1-C6)-alkyl, or (C1-C6)-alkyl-O—(C1-C6)-alkyl, where the radicals are substituted by s radicals selected from the group consisting of cyano, halogen, OR3, and CON(R3)2,
R2 represents (C1-C6)-alkyl,
R3 represents hydrogen or (C1-C6)-alkyl,
n represents 0, 1 or 2, and
s represents 0 or 1.

15. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which
A represents CY,
X represents halogen or (C1-C6)-alkyl,
Y represents S(O)nR2 or (C1-C6)-alkyl-OR1,
Z represents halogen, halo-(C1-C6)-alkyl, or S(O)nR2,
V represents hydrogen,
R and R′ each represent hydrogen,
R1 represents (C1-C6)-alkyl substituted by s halogen radicals,
R2 represents (C1-C6)-alkyl,
n represents 0, 1 or 2, and
s represents 0 or 1.