# Patent

## Title
Aminoquinazoline compounds for combating invertebrate pests

## Abstract

The invention relates to aminoquinazoline compounds or the enantiomers or veterinarily acceptable salts thereof which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to methods for controlling invertebrate pests by using these compounds and to plant propagation material and to agricultural and veterinary compositions comprising said compounds.




wherein A1, A2, A3, A4, R1, R2, R3, R4, R5a, R5b, R5c, R5d and p are defined as in the description.

## Background
This application is a National Stage application of International Application No. PCT/EP2010/063502, filed Sep. 15, 2010, which claims the benefit of U.S. Provisional Application No. 61/245,322, filed Sep. 24, 2009, the entire contents of which are hereby incorporated herein by reference.


The present invention relates to aminoquinazoline compounds or the enantiomers or veterinarily acceptable salts thereof which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to methods for controlling invertebrate pests by using these compounds and to plant propagation material and to agricultural and veterinary compositions comprising said compounds.
Invertebrate pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating invertebrate pests, in particular insects, arachnids and nematodes.
WO 2005/087742 describes quinoline derivatives usable as agents in the control of pests for crop protection, human and animal health, acting as ethanolamine kinase inhibitors.
EP-A-393999 describes quinazolinylsulfonylureidoazines useful as herbicides.
DE-A-19756388 describes substituted 2-aryl-4-amino-quinazolines and their use as cardiovascular agents for treatment of circulatory diseases, blood pressure, angina, pectoris, heart insufficiency, thrombosis or artherosclorosis and to modulate the production of cGMP.
WO 2002/24667 describes 4-amino-quinazolines as glycoprotein IbIX antagonists.
WO 2004/030672 describes the use of 4-amino-quinazolines as anti cancer agents and PKB inhibitors.
WO 2004/092196 describes among other quinazolines derivatives compounds for modulating protein kinase enzymatic activity.
It is an object of the present invention to provide compounds that have a good pesticidal activity, in particular insecticidal activity, and show a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control arthropod pests and/or nematodes.
It has been found that these objectives can be achieved by aminoquinazoline compounds of the formula I below, by their steroisomers and by their salts and N-oxides, in particular their agriculturally or veterinarily acceptable salts.
Therefore, in a first aspect, the invention relates to aminoquinazoline compounds of the formula I and the salts and N-oxides thereof




wherein

    A1, A2, A3 and A4 are N, NX or CR4 wherein X is a lone pair or O, with the proviso that at most three of A1, A2, A3 and A4 are N or NX;
    R1, R2 are selected independently from one another from the group consisting of hydrogen, CN, NO2, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6−;
    
    
     Si(R11)2R12, OR7, S(O)mR7, NR8R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        is saturated or partially saturated,
        comprises 1, 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, wherein the nitrogen and/or the sulfur atom(s) may be oxidized,
        is unsubstituted or substituted with one to five R10, and
        wherein one or two CH2 groups in said heterocyclic ring may be replaced by one or two C═O groups;
    
    
    R3 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
    
    
     Si(R11)2R12, OR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
    
        which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
    
    
     and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated or partially saturated,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
            is unsubstituted or substituted with one to five radicals R10, and
            wherein one or two CH2 groups in said heterocyclic ring may be replaced by one or two C═O groups;
        
        
    
    
    each R4 is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
    
    
     Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl
    
        which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
    
    
     and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated or partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
            is unsubstituted or substituted with one to five radicals R10, and
            wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
        
        
    
    
     or two radicals R4 bound on adjacent carbon atoms together form a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—,
    
        wherein in each of the above group,
        one to five hydrogen atoms independently of each other may be replaced by one to five substituents selected from halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or
        one or two CH2 groups of the above groups may be replaced by one or two C═O groups;
    
    
    R5a is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
    
    
     Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
    
        which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
    
    
     and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        is saturated or partially unsaturated or aromatic,
        
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
            
                is unsubstituted or substituted with one to five radicals R10, and
                wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
            
            
        
        
    
    
     or R5a may form together with the adjacent carbon atom R5b a 5- or 6-membered ring which is at least substituted with one halogen;
    R5b is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy, wherein each mentioned radical
    
        is at least substituted with one halogen,
        may be further partially or fully halogenated, and
        may be substituted with one to five radicals R6;
    
    
     or R5b may form together with the adjacent carbon atom R5c or R5a a 5- or 6-membered ring which is at least substituted with one halogen;
    R5c is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
    
    
     Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)OR7, C(═S)OR7, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl
    
        which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
    
    
     and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        is saturated, partially unsaturated or aromatic,
        comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
        is unsubstituted or substituted with one to five radicals R10, and
        wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
    
    
     or R5c may form together with the adjacent carbon atom R5b or R5d a 5- or 6-membered ring which is at least substituted with one halogen in case of R5b beings involved;
    R5d is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
    
    
     Si(R11)2R12, OR7, S(O)mN(R8)R9, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
    
        which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
    
    
     and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated, partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
            is unsubstituted or substituted with one to five radicals R10, and
            wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
        
        
    
    
     or R5d may form together with the adjacent carbon atom R5c or with R1 or R2 a 5- or 6-membered ring;
    R6 is independently selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
    
        wherein the carbon atom of the aforementioned aliphatic and
        cycloaliphatic radicals may be substituted with one or more Rc;
    
    
     Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
    
        which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
    
    
     and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated, partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
            is unsubstituted or substituted with one to five radicals R10, and
            wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two 0=0 groups;
        
        
    
    
     or two vicinally bound radicals R6 together form a group selected from ═C(Rc)2, ═S(O)mRo, ═S(O)mN(Rn)2, ═NRn and ═NN(Rn)2;
    R7 is independently selected independently from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
    
        wherein the carbon atom of the aforementioned aliphatic and
        cycloaliphatic radicals may be substituted with one or more Rc;
    
    
     Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
    
        which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
    
    
     and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated, partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
            is unsubstituted or substituted with one to five radicals R10, and
            wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;

with the proviso that R7 is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;

        
        
    
    
    R8, R9 are selected independently from one another and independently of each occurrence from the group consisting of hydrogen, CN, NO2, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
    
        wherein the carbon atom of the aforementioned aliphatic and
        cycloaliphatic radicals may be substituted with one or more Rc;
    
    
     Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2 phenyl
    
        which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
    
    
     and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated, partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
            is unsubstituted or substituted with one to five radicals R10, and
            wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
        
        
    
    
    R10 is independently selected independently from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
    
        wherein the carbon atom of the aforementioned aliphatic and
        cycloaliphatic radicals may be substituted with one or more Rc;
    
    
     Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rc)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
    
        which may be substituted with one to five radicals independently selected independently from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
    
    
     and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated or unsaturated,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
            is unsubstituted or substituted with one to five radicals independently selected independently from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
        
        
    
    
     or two radicals R10 bound on adjacent atoms together form a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—,
    
        wherein in each of the above groups,
        one to five hydrogen atoms independently of each other may be replaced by one to five substituents selected from halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or
        one or two or more CH2 groups of the above groups may be replaced by one or two C═O groups;
    
    
    R11, R12 are selected independently of each other and independently of each occurrence from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl;
    Rc is independently selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated, partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
            is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
        
        
    
    
    Ro is independently selected independently from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated, partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
            is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

with the proviso that Ro is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;

        
        
    
    
    Rn is independently selected independently from the group consisting of hydrogen, CN, NO2, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated, partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
            is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
        
        
    
    
    m is independently 0, 1 or 2;
    p is 0, 1, 2, 3 or 4;
    or enantiomers or diastereoisomers thereof or their agriculturally or veterinarily acceptable salts.


The present invention also provides a composition comprising at least one compound of the formula I as defined herein and/or an agriculturally acceptable salt thereof and at least one inert solid/liquid and/or solid carrier
The present invention also provides an agricultural composition comprising at least one compound of the formula I as defined herein and at least one agriculturally acceptable liquid and/or solid carrier.
The present invention also provides a veterinary composition comprising at least one compound of the formula I as defined herein and/or a veterinarily acceptable salt thereof and at least one liquid and/or solid carrier.
The present invention also provides a method for controlling or combating invertebrate pests attack or infestation which method comprises treating the pests, their food supply, their habitat or their breeding, ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, with a pesticidally effective amount of at least one compound of formula I or salt thereof as defined herein.
The present invention also relates to plant propagation material, in particular to seed, comprising at least one compound of formula I or an composition comprising at least one compound of formula I or an agriculturally acceptable salt thereof as defined herein.
The present invention further relates to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of the formula I or a veterinarily acceptable salt thereof as defined herein. Bringing the animal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal.
If used, the term “steroisomers” encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
Depending on the substitution pattern, the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures. Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an imine group.
The compounds of the present invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have a different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.
Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
Suitable agriculturally acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH4+) and substituted ammonium in which one to four of the hydrogen atoms are replaced by C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formula I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
By the term “veterinarily acceptable salts” is meant salts of those cations or anions which are known and accepted in the art for the formation of salts for veterinary use. Suitable acid addition salts, e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorids, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.
The term “invertebrate pest” as used herein encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.
The term “plant propagation material” as used herein includes all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
The term “plants” comprises any types of plants including “non-cultivated plants” and in particular “cultivated plants”.
The term “non-cultivated plants” refers to any wild type species or related species or related genera of a cultivated plant.
The term “cultivated plants” as used herein includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-transitional modification of protein(s) (oligo- or polypeptides) poly for example by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties (e.g. as disclosed in Biotechnol Prog. 2001 July-August; 17(4):720-8, Protein Eng Des Sel. 2004 January; 17(1):57-66, Nat. Protoc. 2007; 2(5):1225-35, Curr. Opin. Chem. Biol. 2006 October; 10(5):487-91. Epub 2006 August 28, Biomaterials. 2001 March; 22(5):405-17, Bioconjug Chem. 2005 January-Feb.; 16(1):113-21).
The term “cultivated plants” as used herein further includes plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxy-phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g. EP-A-0242236, EP-A-242246) or oxynil herbicides (see e.g. U.S. Pat. No. 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e.g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
The term “cultivated plants” as used herein further includes plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus bacillus, particularly from bacillus thuringiensis, such as ä-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 and WO 03/052073. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins protection from harmful pests from certain taxonomic groups of arthropods insects, particularly to beetles (Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera) and to plant parasitic nematodes (Nematoda).
The term “cultivated plants” as used herein further includes plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lyso-zym (e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
The term “cultivated plants” as used herein further includes plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth limiting environ-mental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
The term “cultivated plants” as used herein further includes plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for example oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nexera® rape).
The term “cultivated plants” as used herein further includes plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato).
The organic moieties mentioned in the above definitions of the variables are—like the term halogen—collective terms for individual listings of the individual group members. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group.
The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
The term “C1-C10-alkyl” as used herein and in the alkyl moieties of alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 (“C1-C2-alkyl”), 1 to 4 (“C1-C4-alkyl”), 1 to 6 (“C1-C6-alkyl”), 1 to 8 (“C1-C8-alkyl”) or 1 to 10 (“C1-C10-alkyl”) carbon atoms. C1-C2-alkyl is methyl or ethyl. C1-C4-alkyl is additionally propyl, isopropyl, butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1,1-dimethylethyl (tert-butyl). C1-C6-alkyl is additionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl. C1-C8-alkyl is additionally also, for example, heptyl, octyl, 2-ethylhexyl and positional isomers thereof. C1-C10-alkyl is additionally also, for example, nonyl, decyl and positional isomers thereof.
The term “C1-C10-haloalkyl” as used herein, which is also expressed as “C1-C10-alkyl which is partially or fully halogenated”, refers to straight-chain or branched alkyl groups having 1 to 2 (“C1-C2-haloalkyl”), 1 to 4 (“C1-C4-haloalkyl”), 1 to 6 (“C1-C6-haloalkyl”), 1 to 8 (“C1-C8-haloalkyl”) or 1 to 10 (“C1-C10-haloalkyl”) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular C1-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl.
“Halomethyl” is methyl in which 1, 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
The term “C2-C10-alkenyl” as used herein and in the alkenyl moiety of alkenyloxy and the like refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (“C2-C4-alkenyl”), 2 to 6 (“C2-C6-alkenyl”), 2 to 8 (“C2-C8-alkenyl”), 3 to 8 (“C3-C8-alkenyl”), 2 to 10 (“C2-C10-alkenyl”) or 3 to 10 (“C3-C10-alkenyl”) carbon atoms and a double bond in any position, for example C2-C4-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like, or C2-C10-alkenyl, such as the radicals mentioned for C2-C6-alkenyl and additionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl, 1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-decenyl and the positional isomers thereof.
The term “C2-C10-haloalkenyl” as used herein, which is also expressed as “C1-C10-alkenyl which is partially or fully halogenated”, and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (“C2-C4-haloalkenyl”), 2 to 6 (“C2-C6-haloalkenyl”), 2 to 8 (“C2-C6-haloalkenyl”) or 2 to 10 (“C2-C10-haloalkenyl”) carbon atoms and a double bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.
The term “C2-C10-alkynyl” as used herein and the alkynyl moieties in alkynyloxy, alkynylcarbonyl and the like refers to straight-chain or branched hydrocarbon groups having 2 to 4 (“C2-C4-alkynyl”), 2 to 6 (“C2-C6-alkynyl”), 2 to 8 (“C2-C8-alkynyl”), 3 to 8 (“C3-C8-alkynyl”), 2 to 10 (“C2-C10-alkynyl”) or 3 to 10 (“C3-C8-alkynyl”) carbon atoms and one or two triple bonds in any position, for example C2-C4-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like, C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl and the like;
The term “C2-C10-haloalkynyl” as used herein, which is also expressed as “C1-C10-alkynyl which is partially or fully halogenated”, and the haloalkynyl moieties in haloalkynyloxy, haloalkynylcarbonyl and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (“C2-C4-haloalkynyl”), 3 to 4 (“C3-C4-haloalkynyl”), 2 to 6 (“C2-C6-haloalkynyl”), 3 to 6 (“C3-C6-haloalkynyl”), 2 to 8 (“C2-C8-haloalkynyl”), 3 to 8 (“C3-C8-haloalkynyl”), 2 to 10 (“C2-C10-haloalkynyl”) or 3 to 10 (“C3-C10-haloalkynyl”)carbon atoms and one or two triple bonds in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
The term “C3-C8-cycloalkyl” as used herein refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having 3 to 8, in particular 3 to 6 carbon atoms (“C3-C6-cycloalkyl”). Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
The term “C3-C8-halocycloalkyl” as used herein, which is also expressed as “C3-C8-cycloalkyl which is partially or fully halogenated”, and the halocycloalkyl moieties in halocycloalkoxy, halocycloalkylcarbonyl and the like refers to mono- or bi- or polycyclic saturated hydrocarbon groups having 3 to 8 (“C3-C3-halocycloalkyl”) or preferably 3 to 6 (“C3-C6-halocycloalkyl”) carbon ring members (as mentioned above) in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
The term “C3-C8-cycloalkyl-C1-C4-alkyl” refers to a C3-C8-cycloalkyl group as defined above which is bound to the remainder of the molecule via a C1-C4-alkyl group, as defined above. Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cycloppentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, and the like.
The term “C1-C2-alkoxy” is a C1-C2-alkyl group, as defined above, attached via an oxygen atom. The term “C1-C4-alkoxy” is a C1-C4-alkyl group, as defined above, attached via an oxygen atom. The term “C1-C6-alkoxy” is a C1-C6-alkyl group, as defined above, attached via an oxygen atom. The term “C1-C10-alkoxy” is a C1-C10-alkyl group, as defined above, attached via an oxygen atom. C1-C2-alkoxy is methoxy or ethoxy. C1-C4-alkoxy is additionally, for example, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). C1-C6-alkoxy is additionally, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy. C1-C8-alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. C1-C10-alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.
The term “C1-C2-haloalkoxy” is a C1-C2-haloalkyl group, as defined above, attached via an oxygen atom. The term “C1-C4-haloalkoxyl” is a C1-C4-haloalkyl group, as defined above, attached via an oxygen atom. The term “C1-C6-haloalkoxy” is a C1-C6-haloalkyl group, as defined above, attached via an oxygen atom. The term “C1-C10-haloalkoxy” is a C1-C10-haloalkyl group, as defined above, attached via an oxygen atom. C1-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5. C1-C4-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2—C2F5, OCF2—C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C1-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
The term “C1-C2-alkylthio” is a C1-C2-alkyl group, as defined above, attached via a sulfur atom. The term “C1-C4-alkylthio” is a C1-C4-alkyl group, as defined above, attached via a sulfur atom. The term “C1-C6-alkylthio” is a C1-C6-alkyl group, as defined above, attached via a sulfur atom. The term “C1-C10-alkylthio” is a C1-C10-alkyl group, as defined above, attached via a sulfur atom. C1-C2-alkylthio is methylthio or ethylthio. C1-C4-alkylthio is additionally, for example, n-propylthio, 1-methylethylthio (isopropylthio), butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1,1-dimethylethylthio (tert-butylthio). C1-C6-alkylthio is additionally, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio. C1-C8-alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof. C1-C10-alkylthio is additionally, for example, nonylthio, decylthio and positional isomers thereof.
The term “C1-C2-haloalkylthio” is a C1-C2-haloalkyl group, as defined above, attached via a sulfur atom. The term “C1-C4-haloalkylthio” is a C1-C4-haloalkyl group, as defined above, attached via a sulfur atom. The term “C1-C6-haloalkylthio” is a C1-C6-haloalkyl group, as defined above, attached via a sulfur atom. The term “C1-C10-haloalkylthio” is a C1-C10-haloalkyl group, as defined above, attached via a sulfur atom. C1-C2-haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2Cl, SCHCl2, SCCl3, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC2F5. C1-C4-Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH2—C2F5, SCF2—C2F5, 1-(CH2F)-2-fluoroethylthio, 1-(CH2Cl)-2-chloroethylthio, 1-(CH2Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. C1-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.
The term “C1-C2-alkylsulfinyl” is a C1-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C4-alkylsulfinyl” is a C1-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C6-alkylsulfinyl” is a C1-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C10-alkylsulfinyl” is a C1-C10-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. C1-C2-Alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C1-C4-Alkylsulfinyl is additionally, for example, n-propylsulfinyl, 1-methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or 1,1-dimethylethylsulfinyl (tert-butylsulfinyl). C1-C6-Alkylsulfinyl is additionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl. C1-C8-Alkylsulfinyl is additionally, for example, heptylsulfinyl, octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof. C1-C10-Alkylsulfinyl is additionally, for example, nonylsulfinyl, decylsulfinyl and positional isomers thereof.
The term “C1-C2-haloalkylsulfinyl” is a C1-C2-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C4-haloalkylsulfinyl” is a C1-C4-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C6-haloalkylsulfinyl” is a C1-C6-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C10-haloalkylsulfinyl” is a C1-C10-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. C1-C2-Haloalkylsulfinyl is, for example, S(O)CH2F, S(O)CHF2, S(O)CF3, S(O)CH2Cl, S(O)CHCl2, S(O)CCl3, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl or S(O)C2F5. C1-C4-Haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl, 2-bromopropylsulfinyl, 3-brornopropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, S(O)CH2—C2F5, S(O)CF2—C2F5, 1-(CH2F)-2-fluoroethylsulfinyl, 1-(CH2Cl)-2-chloroethylsulfinyl, 1-(CH2Br)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl. C1-C6-Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.
The term “C1-C2-alkylsulfonyl” is a C1-C2-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C4-alkylsulfonyl” is a C1-C4-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C6-alkylsulfonyl” is a C1-C6-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C10-alkylsulfonyl” is a C1-C10-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. C1-C2-Alkylsulfonyl is methylsulfonyl or ethylsulfonyl. C1-C4-Alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1-methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1-methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1,1-dimethylethylsulfonyl (tert-butylsulfonyl). C1-C6-Alkylsulfonyl is additionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dinnethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl. C1-C8-Alkylsulfonyl is additionally, for example, heptylsulfonyl, octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof. C1-C10-Alkylsulfonyl is additionally, for example, nonylsulfonyl, decylsulfonyl and positional isomers thereof.
The term “C1-C2-haloalkylsulfonyl” is a C1-C2-haloalkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C4-haloalkylsulfonyl” is a C1-C4-haloalkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C8-haloalkylsulfonyl” is a C1-C8-haloalkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C10-haloalkylsulfonyl” is a C1-C10-haloalkyl group, as defined above, attached via a sulfonyl [S(O)2] group. C1-C2-Haloalkylsulfonyl is, for example, S(O)2CH2F, S(O)2CHF2, S(O)2CF3, S(O)2CH2Cl, S(O)2CHCl2, S(O)2CCl3, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl or S(O)2C2F5. C1-C4-Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, S(O)2CH2—C2F5, S(O)2CF2—C2F5, 1-(CH2F)-2-fluoroethylsulfonyl, 1-(CH2Cl)-2-chloroethylsulfonyl, 1-(CH2Br)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl. C1-C6-Haloalkylsulfonyl is additionally, for example, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl.
The term “3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups (if one or two or at most three heteroatoms of the heterocyclic ring are oxidzed) selected from N, O, S, NO, SO and SO2, as ring members” as used herein refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic. The heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring include: Oxiranyl, aziridinyl, azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl, 2-morphollnyl, 3-morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, hexahydrooxepinyl, hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl, hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl, hexahydro-1,3-dioxepinyl, hexahydro-1,4-dioxepinyl and the like.
Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- or tetrahydrotriazin-2-yl, 1,2,4-di- or tetrahydrotriazin-3-yl, 2,3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1′-1]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or 2,3,4,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl, tetrahydro-1,3-oxazepinyl, tetrahydro-1,4-oxazepinyl, tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.
3-, 4-, 5-, 6- or 7-membered aromatic heterocyclic ring is 5- or 6-membered aromatic heterocyclic (hetaryl). Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
The remarks made below concerning preferred embodiments of the variables of the compounds of formula I, especially with respect to their substituents A1, A2, A3, A4, R1, R2, R3, R4, R5a, R5b, R5c, R5d, R6, R7, R8, R9, R10, R11, R12, Rc, Rn, Ro, m, and p the features of the use and method according to the invention and of the composition of the invention are valid both on their own and, in particular, in every possible combination with each other.
The radical A when used in the text is as following defined:




wherein # denotes the binding site to the remainder of formula I and wherein the variables p, R3, R4, A1, A2, A3 and A4 are as defined in formula I.

As a matter of course, the p radicals R4 replace a hydrogen atom on a carbon ring atom. For instance, if A1, A2, A3 or A4 is defined to be CH and if this position is to be substituted by a radical R4, then A1, A2, A3 or A4 is of course a substituted C—R4. If there is more than one radical R4, these substituents R4 can be the same or different.
Preferably, at most two of A1, A2, A3 and A4 are N.
In a preferred embodiment, A′, A2, A3 and A4 are CR4. In the case that more than one substituent R4 is present in the radical A, the different R4 are selected independently from each other. In case p is 2, the two substituents R4 are preferably bound on the position of A1 and A2. In case p is 1, the substituent R4 is preferably bound on the position of A1 or A2.
In analogy to the above cited meaning of A, A3 and A4 are respectively equivalent to A2 and A1 and thus have the same definition of preferencies.
Preferably, three of A1, A2, A3 and A4 are CH and the remaining radical is a substituted CR4. Even more preferably, A2, A3, A4 and A1 are CH.
In one embodiment,

    R3 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
    
    
     Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and
     a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated, partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
            is unsubstituted or substituted by one to five radicals R10 and wherein one or two CH2 groups in said saturated or partially saturated heterocyclic rings may be replaced by one or two C═O groups.
        
        
    
    


In another embodiment, R3 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-cycloalkoxy wherein the last four mentioned radicals are preferably at least substituted by one halogen, Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6 and C(═NR8)R6.
Within these embodiments, R3 is preferably selected from the group consisting of hydrogen, halogen, cyano, nitro, SR7, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C3-C6-cycloalkoxy wherein the four last mentioned group are preferably at least substituted by one halogen and wherein the five last mentioned radicals may be substituted by one to five radicals R6.
More preferably, R3 is selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy wherein the two last mentioned radicals are at least substituted by one halogen.
Even more preferably, R3 is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, NO2, CF3, CHF2, CH2F, CF2Cl, CFCl2, CCl3, OCF3, OCHF2 and OCF2CHF2.
More particularly, R3 is preferably fluorine or chlorine or bromine.
In an embodiment,

    R4 is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10 alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
     Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and
     a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
     wherein said heterocyclic ring
    
        is saturated or partially unsaturated or aromatic,
        comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 
        is unsubstituted or substituted by one to five radicals R10 and
        wherein one or two CH2 groups in said saturated or partially saturated heterocyclic rings may be replaced by one or two C═O groups;

or two radicals R4 bound on adjacent carbon atoms together form a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH—CHCH2—, —CH2CH2O, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—, wherein in each of the above groups one to five hydrogen atoms may be replaced by one to five substituents selected from halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy or one or two CH2 groups of the above groups may be replaced by one or two C═O groups.

    
    


In another embodiment,

    R4 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
    
    
     Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl,
    
        which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and
    
    
     a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
    
        wherein said heterocyclic ring
        
            is saturated or partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO SO and SO2,
            is unsubstituted or substituted by one to five radicals R10 and
            wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups.
        
        
    
    


In a further embodiment,

    R4 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C3-C5-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
    
    
     Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, C(═O)N(R8)R9 and C(═S)N(R8)R9.


Within these embodiments, R4 is preferably selected from the group consisting of hydrogen, halogen, cyano, nitro, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy wherein the four last mentioned radicals if substituted are preferably substituted by one halogen and wherein the five last mentioned groups may be substituted by one to five radicals R6.
More preferably, R4 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C1-C6-alkyl and C1-C6-haloalkyl.
Even more preferably, R4 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, CF3 and CHF2.
More particularly, R4 is hydrogen.
Examples of suitable radicals A are the radicals numbered A1a1 to A1a98 which are radicals of the formula A as above depicted wherein A2, A3, A4 are CH, A1 is CR4, and R4 and R3 are as defined in one row of the following Table B (radicals A1a1 to A1a98):











TABLE B







Radical A
R3
R4









A1a1
F
H



A1a2
Cl
H



A1a3
Br
H



A1a4
I
H



A1a5
CN
H



A1a6
NO2
H



A1a7
CF3
H



A1a8
CHF2
H



A1a9
CH2F
H



A1a10
CF2Cl
H



A1a11
CFCl2
H



A1a12
CCl3
H



A1a13
OCHF2
H



A1a14
SCF3
H



A1a15
F
F



A1a16
Cl
F



A1a17
Br
F



A1a18
I
F



A1a19
CN
F



A1a20
NO2
F



A1a21
CF3
F



A1a22
CHF2
F



A1a23
CH2F
F



A1a24
CF2Cl
F



A1a25
CFCl2
F



A1a26
CCl3
F



A1a27
OCHF2
F



A1a28
SCF3
F



A1a29
F
Cl



A1a30
Cl
Cl



A1a31
Br
Cl



A1a32
I
Cl



A1a33
CN
Cl



A1a34
NO2
Cl



A1a35
CF3
Cl



A1a36
CHF2
Cl



A1a37
CH2F
Cl



A1a38
CF2Cl
Cl



A1a39
CFCl2
Cl



A1a40
CCl3
Cl



A1a41
OCHF2
Cl



A1a42
SCF3
Cl



A1a43
F
Br



A1a44
Cl
Br



A1a45
Br
Br



A1a46
I
Br



A1a47
CN
Br



A1a48
NO2
Br



A1a49
CF3
Br



A1a50
CHF2
Br



A1a51
CH2F
Br



A1a52
CF2Cl
Br



A1a53
CFCl2
Br



A1a54
CCl3
Br



A1a55
OCHF2
Br



A1a56
SCF3
Br



A1a57
F
CN



A1a58
Cl
CN



A1a59
Br
CN



A1a60
I
CN



A1a61
CN
CN



A1a62
NO2
CN



A1a63
CF3
CN



A1a64
CHF2
CN



A1a65
CH2F
CN



A1a66
CF2Cl
CN



A1a67
CFCl2
CN



A1a68
CCl3
CN



A1a69
OCHF2
CN



A1a70
SCF3
CN



A1a71
F
Me



A1a72
Cl
Me



A1a73
Br
Me



A1a74
I
Me



A1a75
CN
Me



A1a76
NO2
Me



A1a77
CF3
Me



A1a78
CHF2
Me



A1a79
CH2F
Me



A1a80
CF2Cl
Me



A1a81
CFCl2
Me



A1a82
CCl3
Me



A1a83
OCHF2
Me



A1a84
SCF3
Me



A1a85
F
CF3



A1a86
Cl
CF3



A1a87
Br
CF3



A1a88
I
CF3



A1a89
CN
CF3



A1a90
NO2
CF3



A1a91
CF3
CF3



A1a92
CHF2
CF3



A1a93
CH2F
CF3



A1a94
CF2Cl
CF3



A1a95
CFCl2
CF3



A1a96
CCl3
CF3



A1a97
OCHF2
CF3



A1a98
SCF3
CF3










Analog to the above listed Table B, further examples of suitable radicals A are the radicals of the formula A numbered A1a99 to A1a197 wherein A1, A3, A4 are CH, A2 is CR4, and R4 and R3 for each radical A have the meaning of one line in Table B.
In a particular embodiment of the invention, each example of radical A numbered A1a1 to A1a197 is a preferred radical A in formula I.
In an embodiment,

    R5a is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, —SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6,
    
    
     Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl,
    
        which may be substituted by 1, 2, 3, 4 or 5 radicals R10;
    
    
     and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring
    
        wherein said heterocyclic ring
        
            is saturated or partially unsaturated or aromatic,
            comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
            is unsubstituted or substituted by one to five radicals R10, and
            wherein one or two CH2 groups in said saturated or partially saturated rings may be by one or two C═O groups;
        
        
    
    
    or R5a may form together with the adjacent carbon atom R5b a 5- or 6-membered ring which is at least substituted by one halogen.


More preferably,

    R5a is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
    
        wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
    
    
     Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6 and C(═NR8)R6.


More preferably, R5a is selected from the group consisting of hydrogen, halogen, cyano, nitro, SCF3, SOCF3, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy wherein the last four mentioned radicals may be substituted by one halogen.
More preferably, R5a is selected from the group consisting of hydrogen, halogen, cyano, nitro, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy (e.g. OCF3, OCHF2, OCF2CHF2) and C1-C6-cycloalkoxy wherein the five last mentioned group may be substituted by halogen.
Even more preferably, R5a is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl and C1-C6-haloalkyl.
Even more preferably, R5a is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, CH3, CF3, CHF2, CH2F, CF2Cl, CFCl2 and CCl3.
Even more preferably, R5a is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, CF3 and CHF2.
More particularly, R5a is hydrogen.
In a embodiment,

    R5b is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, alkoxy and C1-C6-cycloalkoxy, wherein each mentioned radical
    
        is at least substituted with one halogen,
        may be further partially or fully halogenated and
        may be substituted with one to five radicals R6;
    
    
    or may form together with the adjacent carbon atom R5c or R5a a 5- or 6-membered ring which is at least substituted with one halogen.


Within the above embodiment, R5b is preferably selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy and wherein each mentioned radical is at least substituted with one halogen.
Within the above embodiments, R5b is preferably selected from the group consisting of C1-C6-haloalkyl and C1-C6-haloalkoxy.
Even more preferably, R5b is selected from the group consisting of CF3, CHF2, CH2F, CF2F3, CF(CF3)2, COH(CF3)2, CF2Cl, CFCl2, CCl3, OCF3, OCHF2, OCF2CF3, OCF2CHF2, OCF(CF3)2, OCF2Cl, OCFCl2 and OCCl3.
Even more preferably, R5b is selected from the group consisting of CF3, CHF2, CF2F3, CF(CF3)2, COH(CF3)2, CF2Cl, CFCl2, CCl3, OCF3, OCHF2, OCF2CF3, OCF2CHF2, OCF(CF3)2, OCF2Cl, OCFCl2 and OCCl3.
More particularly R5b is CF3.
Preferably, R5c is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C3-C8-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the last four mentioned groups may be partially or fully halogenated and/or may be substituted with one to five radicals R6.
More preferably, R5c is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl and C1-C6-haloalkyl.
More particularly, R5c is hydrogen.
Preferably, R5d is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C3-C8-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the last four mentioned groups may be partially or fully halogenated and/or may be substituted with one to five radicals R6.
More preferably, R5d is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl and C1-C6-haloalkyl.
More particularly, R5d is hydrogen.
In case R6 is a substituent on an alkyl, alkenyl or alkynyl group, it is preferably selected from the group consisting of

    
    
        hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
        
            wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;
        
        
        Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)nRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl,
        
            which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and
        
        
        a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
        
            wherein said heterocyclic ring
            
                is saturated or partially unsaturated or aromatic,
                comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
                is unsubstituted or substituted with one to five radicals R10, and
                wherein one or two CH2 groups in said saturated or partially saturated heterocyclic rings may be replaced by one or two C═O groups.
            
            
        
        
    
    


In case R6 is a substituent on an alkyl, alkenyl or alkynyl group, it is more preferably selected from the group consisting of

    
    
        halogen, cyano, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, ORo, SRo, phenyl,
        
            which may be substituted with 1, 2, 3, 4 or 5 radicals R10, and
        
        
        a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
        
            wherein said heterocyclic ring
            
                is saturated or partially unsaturated or aromatic,
                comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2,
                is unsubstituted or substituted with one or more radicals R10;
            
            
        
        
        wherein Ro and R10 have one of the meanings given above or in particular one of the preferred meanings given below.
    
    


In case R6 is a substituent on an alkyl, alkenyl or alkynyl group, it is even more preferably selected from the group consisting of halogen, cyano, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, phenyl which may be substituted with 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S, wherein the heteroaromatic ring may be substituted with one or more radicals R10; and
wherein R10 has one of the meanings given above or in particular one of the preferred meanings given below.
In case R6 is a substituent on an alkyl, alkenyl or alkynyl group, it is in particular selected from the group consisting of halogen and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S, wherein the heteroaromatic ring is unsubstituted or substituted with one or more radicals R10; and
wherein R10 has one of the meanings given above or in particular one of the preferred meanings given below.
In case R6 is a substituent on a cycloalkyl group, it is preferably selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein said heterocyclic ring is saturated or partially unsaturated or aromatic, comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 and wherein said heterocyclic ring is unsubstituted or substituted with one or more radicals R10;
or two vicinally bound radicals R6 together form a group selected from ═C(Rc)2, S(O)mRc, ═S(O)mN(Rn)2, ═NRn, and ═NN(Rn)2;
or two radicals R6, together with the carbon atoms to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2;

wherein Rc, Rn, Ro, R10, R11 and R12 have one of the meanings given above or in particular one of the preferred meanings given below.

In case R6 is a substituent on a cycloalkyl group, it is more preferably selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, ORo, SRo, S(O)mRo, S(O)mN(Rn)2, N(Rn)2, C(═O)N(Rn)2, C(═S)N(Rn)2, C(═O)Ro, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted with one or more radicals R10;
wherein Rc, Rn, Ro and R10 have one of the meanings given above or in particular one of the preferred meanings given below.
In case R6 is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of halogen, C1-C4-alkyl, C1-C3-haloalkyl, C1-C4-alkoxy and C1-C3-haloalkoxy. In particular, R6 as a substituent on a cycloalkyl group is selected from halogen, C1-C4-alkyl and C1-C3-haloalkyl.
In case R6 is a substituent on C(═O), C(═S) or C(═NR8), it is preferably selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, —ORo, —SRo, —N(Rn)2, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, wherein the heterocyclic ring may be substituted with one or more radicals R10;
wherein Rc, Rn, Ro and R10 have one of the meanings given above or in particular one of the preferred meanings given below.
In case R6 is a substituent on C(═O), C(═S) or C(═NR8), it is more preferably selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, wherein the heterocyclic ring may be substituted by one or more radicals R10;
wherein R10 has one of the meanings given above or in particular one of the preferred meanings given below.
In case R6 is a substituent on C(═O), C(═S) or C(═NR8), it is even more preferably selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C3-haloalkoxy, phenyl which may be substituted with 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S, wherein the heteroaromatic ring may be substituted with one or more radicals R10;
wherein R10 has one of the meanings given above or in particular one of the preferred meanings given below.
Preferably, each R7 is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, wherein the heterocyclic ring is unsubstituted or substituted with. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10, wherein R10 has one of the meanings given above or in particular one of the preferred meanings given below.
More preferably, each R7 is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, phenyl which is unsubstituted or substituted by 1, 2, 3, 4 or 5 radicals R10; and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S, wherein the heteroaromatic ring may be substituted by one or more radicals R10; where R10 has one of the meanings given above or in particular one of the preferred meanings given below.
R8 and R9 are independently of each other and independently of each occurrence preferably selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, where the heterocyclic ring may be substituted by one or more radicals R10; and wherein R10 has one of the meanings given above or in particular one of the preferred meanings given below.
R8 and R9 are independently of each other and independently of each occurrence more preferably selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S, as ring members, wherein the heteroaromatic ring is unsubstituted or substituted by one or more radicals R10; and wherein R10 has one of the meanings given above or in particular one of the preferred meanings given below.
In particular, R8 and R9 are independently of each other and independently of each occurrence selected from the group consisting of hydrogen and C1-C4-alkyl. Preferably, each R10 is independently selected from the group consisting of halogen, cyano, C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals Rc, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals Rc, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, N(Rn)2, C(═O)Rc, C(═O)N(Rn)2, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy; and a 3-, 4-, 5-, 6- or 7-membered saturated or unsaturated heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, which may be substituted by one or more radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
or two radicals R10 bound on adjacent atoms together form a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, and —O(CH2)O—, thus forming, together with the atoms to which they are bound, a 5- or 6-membered ring, where the hydrogen atoms of the above groups may be replaced by one or more substituents selected from halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy or one or more CH2 groups of the above groups may be replaced by a C═O group,

where Rc, Rn and Ro have one of the general or in particular one of the preferred meanings given above.

More preferably, each R10 is independently selected from the group consisting of halogen, cyano, C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals Rc, —ORn, —N(Rn)2, C(═O)Rc, —C(═O)ORo, —C(═O)N(Rn)2, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy and C1-C6-haloalkoxy; and a 3-, 4-, 5-, 6- or 7-membered saturated or unsaturated heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, which may be substituted by one or more radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
where Rc, Rn, Ro have one of the general or in particular one of the preferred meanings given above.
Even more preferably, each R10 is independently selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy. In particular, each R10 is independently selected from the group consisting of halogen, C1-C4-alkyl and C1-C4-haloalkyl and is specifically halogen, more specifically chlorine.
Preferably, R11 and R12 are, independently of each other and independently of each occurrence, selected from C1-C4-alkyl and are in particular methyl.
A very preferred embodiment of the invention relates to the compounds of the formula (I-a)




wherein

A has one of the general meaning as defined here above;
A is in particular one of the preferred radical A numbered A1a1 to A1a197 as defined in table B above.
R5b, R5a, R1 and R2 have one of the general meaning or one of the preferred meaning as here above defined.
In particular, R5b, R1, and R2 have the meaning Ib numbered Ib1 to Ib1168 as defined in each line of the following Table C. It is to note that R1 and R2 are permutable in the meaning of Ib1009 to Ib1168.












TABLE C







Ib
R5b
R1
R2









Ib1
CF3
Me
Me



Ib2
CHF2
Me
Me



Ib3
CF2CF3
Me
Me



Ib4
CF(CF3)2
Me
Me



Ib5
COH(CF3)2
Me
Me



Ib6
CF2Cl
Me
Me



Ib7
CFCl2
Me
Me



Ib8
CCl3
Me
Me



Ib9
OCF3
Me
Me



Ib10
OCHF2
Me
Me



Ib11
OCF2CF3
Me
Me



Ib12
OCF2CHF2
Me
Me



Ib13
OCF(CF3)2
Me
Me



Ib14
OCF2Cl
Me
Me



Ib15
OCFCl2
Me
Me



Ib16
OCCl3
Me
Me



Ib17
CF3
Me
Et



Ib18
CHF2
Me
Et



Ib19
CF2CF3
Me
Et



Ib20
CF(CF3)2
Me
Et



Ib21
COH(CF3)2
Me
Et



Ib22
CF2Cl
Me
Et



Ib23
CFCl2
Me
Et



Ib24
CCl3
Me
Et



Ib25
OCF3
Me
Et



Ib26
OCHF2
Me
Et



Ib27
OCF2CF3
Me
Et



Ib28
OCF2CHF2
Me
Et



Ib29
OCF(CF3)2
Me
Et



Ib30
OCF2Cl
Me
Et



Ib31
OCFCl2
Me
Et



Ib32
OCCl3
Me
Et



Ib33
CF3
Me
Pr



Ib34
CHF2
Me
Pr



Ib35
CF2CF3
Me
Pr



Ib36
CF(CF3)2
Me
Pr



Ib37
COH(CF3)2
Me
Pr



Ib38
CF2Cl
Me
Pr



Ib39
CFCl2
Me
Pr



Ib40
CCl3
Me
Pr



Ib41
OCF3
Me
Pr



Ib42
OCHF2
Me
Pr



Ib43
OCF2CF3
Me
Pr



Ib44
OCF2CHF2
Me
Pr



Ib45
OCF(CF3)2
Me
Pr



Ib46
OCF2Cl
Me
Pr



Ib47
OCFCl2
Me
Pr



Ib48
OCCl3
Me
Pr



Ib49
CF3
Me
iPr



Ib50
CHF2
Me
iPr



Ib51
CF2CF3
Me
iPr



Ib52
CF(CF3)2
Me
iPr



Ib53
COH(CF3)2
Me
iPr



Ib54
CF2Cl
Me
iPr



Ib55
CFCl2
Me
iPr



Ib56
CCl3
Me
iPr



Ib57
OCF3
Me
iPr



Ib58
OCHF2
Me
iPr



Ib59
OCF2CF3
Me
iPr



Ib60
OCF2CHF2
Me
iPr



Ib61
OCF(CF3)2
Me
iPr



Ib62
OCF2Cl
Me
iPr



Ib63
OCFCl2
Me
iPr



Ib64
OCCl3
Me
iPr



Ib65
CF3
Me
Bu



Ib66
CHF2
Me
Bu



Ib67
CF2CF3
Me
Bu



Ib68
CF(CF3)2
Me
Bu



Ib69
COH(CF3)2
Me
Bu



Ib70
CF2Cl
Me
Bu



Ib71
CFCl2
Me
Bu



Ib72
CCl3
Me
Bu



Ib73
OCF3
Me
Bu



Ib74
OCHF2
Me
Bu



Ib75
OCF2CF3
Me
Bu



Ib76
OCF2CHF2
Me
Bu



Ib77
OCF(CF3)2
Me
Bu



Ib78
OCF2Cl
Me
Bu



Ib79
OCFCl2
Me
Bu



Ib80
OCCl3
Me
Bu



Ib81
CF3
Me
Pn



Ib82
CHF2
Me
Pn



Ib83
CF2CF3
Me
Pn



Ib84
CF(CF3)2
Me
Pn



Ib85
COH(CF3)2
Me
Pn



Ib86
CF2Cl
Me
Pn



Ib87
CFCl2
Me
Pn



Ib88
CCl3
Me
Pn



Ib89
OCF3
Me
Pn



Ib90
OCHF2
Me
Pn



Ib91
OCF2CF3
Me
Pn



Ib92
OCF2CHF2
Me
Pn



Ib93
OCF(CF3)2
Me
Pn



Ib94
OCF2Cl
Me
Pn



Ib95
OCFCl2
Me
Pn



Ib96
OCCl3
Me
Pn



Ib97
CF3
Me
Me—cPr



Ib98
CHF2
Me
Me—cPr



Ib99
CF2CF3
Me
Me—cPr



Ib100
CF(CF3)2
Me
Me—cPr



Ib101
COH(CF3)2
Me
Me—cPr



Ib102
CF2Cl
Me
Me—cPr



Ib103
CFCl2
Me
Me—cPr



Ib104
CCl3
Me
Me—cPr



Ib105
OCF3
Me
Me—cPr



Ib106
OCHF2
Me
Me—cPr



Ib107
OCF2CF3
Me
Me—cPr



Ib108
OCF2CHF2
Me
Me—cPr



Ib109
OCF(CF3)2
Me
Me—cPr



Ib110
OCF2Cl
Me
Me—cPr



Ib111
OCFCl2
Me
Me—cPr



Ib112
OCCl3
Me
Me—cPr



Ib113
CF3
Me
allyl



Ib114
CHF2
Me
allyl



Ib115
CF2CF3
Me
allyl



Ib116
CF(CF3)2
Me
allyl



Ib117
COH(CF3)2
Me
allyl



Ib118
CF2Cl
Me
allyl



Ib119
CFCl2
Me
allyl



Ib120
CCl3
Me
allyl



Ib121
OCF3
Me
allyl



Ib122
OCHF2
Me
allyl



Ib123
OCF2CF3
Me
allyl



Ib124
OCF2CHF2
Me
allyl



Ib125
OCF(CF3)2
Me
allyl



Ib126
OCF2Cl
Me
allyl



Ib127
OCFCl2
Me
allyl



Ib128
OCCl3
Me
allyl



Ib129
CF3
Me
propargyl



Ib130
CHF2
Me
propargyl



Ib131
CF2CF3
Me
propargyl



Ib132
CF(CF3)2
Me
propargyl



Ib133
COH(CF3)2
Me
propargyl



Ib134
CF2Cl
Me
propargyl



Ib135
CFCl2
Me
propargyl



Ib136
CCl3
Me
propargyl



Ib137
OCF3
Me
propargyl



Ib138
OCHF2
Me
propargyl



Ib139
OCF2CF3
Me
propargyl



Ib140
OCF2CHF2
Me
propargyl



Ib141
OCF(CF3)2
Me
propargyl



Ib142
OCF2Cl
Me
propargyl



Ib143
OCFCl2
Me
propargyl



Ib144
OCCl3
Me
propargyl



Ib145
CF3
Me
Me—CN



Ib146
CHF2
Me
Me—CN



Ib147
CF2CF3
Me
Me—CN



Ib148
CF(CF3)2
Me
Me—CN



Ib149
COH(CF3)2
Me
Me—CN



Ib150
CF2Cl
Me
Me—CN



Ib151
CFCl2
Me
Me—CN



Ib152
CCl3
Me
Me—CN



Ib153
OCF3
Me
Me—CN



Ib154
OCHF2
Me
Me—CN



Ib155
OCF2CF3
Me
Me—CN



Ib156
OCF2CHF2
Me
Me—CN



Ib157
OCF(CF3)2
Me
Me—CN



Ib158
OCF2Cl
Me
Me—CN



Ib159
OCFCl2
Me
Me—CN



Ib160
OCCl3
Me
Me—CN



Ib161
CF3
Et
Et



Ib162
CHF2
Et
Et



Ib163
CF2CF3
Et
Et



Ib164
CF(CF3)2
Et
Et



Ib165
COH(CF3)2
Et
Et



Ib166
CF2Cl
Et
Et



Ib167
CFCl2
Et
Et



Ib168
CCl3
Et
Et



Ib169
OCF3
Et
Et



Ib170
OCHF2
Et
Et



Ib171
OCF2CF3
Et
Et



Ib172
OCF2CHF2
Et
Et



Ib173
OCF(CF3)2
Et
Et



Ib174
OCF2Cl
Et
Et



Ib175
OCFCl2
Et
Et



Ib176
OCCl3
Et
Et



Ib177
CF3
Et
Pr



Ib178
CHF2
Et
Pr



Ib179
CF2CF3
Et
Pr



Ib180
CF(CF3)2
Et
Pr



Ib181
COH(CF3)2
Et
Pr



Ib182
CF2Cl
Et
Pr



Ib183
CFCl2
Et
Pr



Ib184
CCl3
Et
Pr



Ib185
OCF3
Et
Pr



Ib186
OCHF2
Et
Pr



Ib187
OCF2CF3
Et
Pr



Ib188
OCF2CHF2
Et
Pr



Ib189
OCF(CF3)2
Et
Pr



Ib190
OCF2Cl
Et
Pr



Ib191
OCFCl2
Et
Pr



Ib192
OCCl3
Et
Pr



Ib193
CF3
Et
iPr



Ib194
CHF2
Et
iPr



Ib195
CF2CF3
Et
iPr



Ib196
CF(CF3)2
Et
iPr



Ib197
COH(CF3)2
Et
iPr



Ib198
CF2Cl
Et
iPr



Ib199
CFCl2
Et
iPr



Ib200
CCl3
Et
iPr



Ib201
OCF3
Et
iPr



Ib202
OCHF2
Et
iPr



Ib203
OCF2CF3
Et
iPr



Ib204
OCF2CHF2
Et
iPr



Ib205
OCF(CF3)2
Et
iPr



Ib206
OCF2Cl
Et
iPr



Ib207
OCFCl2
Et
iPr



Ib208
OCCl3
Et
iPr



Ib209
CF3
Et
Bu



Ib210
CHF2
Et
Bu



Ib211
CF2CF3
Et
Bu



Ib212
CF(CF3)2
Et
Bu



Ib213
COH(CF3)2
Et
Bu



Ib214
CF2Cl
Et
Bu



Ib215
CFCl2
Et
Bu



Ib216
CCl3
Et
Bu



Ib217
OCF3
Et
Bu



Ib218
OCHF2
Et
Bu



Ib219
OCF2CF3
Et
Bu



Ib220
OCF2CHF2
Et
Bu



Ib221
OCF(CF3)2
Et
Bu



Ib222
OCF2Cl
Et
Bu



Ib223
OCFCl2
Et
Bu



Ib224
OCCl3
Et
Bu



Ib225
CF3
Et
Pn



Ib226
CHF2
Et
Pn



Ib227
CF2CF3
Et
Pn



Ib228
CF(CF3)2
Et
Pn



Ib229
COH(CF3)2
Et
Pn



Ib230
CF2Cl
Et
Pn



Ib231
CFCl2
Et
Pn



Ib232
CCl3
Et
Pn



Ib233
OCF3
Et
Pn



Ib234
OCHF2
Et
Pn



Ib235
OCF2CF3
Et
Pn



Ib236
OCF2CHF2
Et
Pn



Ib237
OCF(CF3)2
Et
Pn



Ib238
OCF2Cl
Et
Pn



Ib239
OCFCl2
Et
Pn



Ib240
OCCl3
Et
Pn



Ib241
CF3
Et
Me—cPr



Ib242
CHF2
Et
Me—cPr



Ib243
CF2CF3
Et
Me—cPr



Ib244
CF(CF3)2
Et
Me—cPr



Ib245
COH(CF3)2
Et
Me—cPr



Ib246
CF2Cl
Et
Me—cPr



Ib247
CFCl2
Et
Me—cPr



Ib248
CCl3
Et
Me—cPr



Ib249
OCF3
Et
Me—cPr



Ib250
OCHF2
Et
Me—cPr



Ib251
OCF2CF3
Et
Me—cPr



Ib252
OCF2CHF2
Et
Me—cPr



Ib253
OCF(CF3)2
Et
Me—cPr



Ib254
OCF2Cl
Et
Me—cPr



Ib255
OCFCl2
Et
Me—cPr



Ib256
OCCl3
Et
Me—cPr



Ib257
CF3
Et
allyl



Ib258
CHF2
Et
allyl



Ib259
CF2CF3
Et
allyl



Ib260
CF(CF3)2
Et
allyl



Ib261
COH(CF3)2
Et
allyl



Ib262
CF2Cl
Et
allyl



Ib263
CFCl2
Et
allyl



Ib264
CCl3
Et
allyl



Ib265
OCF3
Et
allyl



Ib266
OCHF2
Et
allyl



Ib267
OCF2CF3
Et
allyl



Ib268
OCF2CHF2
Et
allyl



Ib269
OCF(CF3)2
Et
allyl



Ib270
OCF2Cl
Et
allyl



Ib271
OCFCl2
Et
allyl



Ib272
OCCl3
Et
allyl



Ib273
CF3
Et
propargyl



Ib274
CHF2
Et
propargyl



Ib275
CF2CF3
Et
propargyl



Ib276
CF(CF3)2
Et
propargyl



Ib277
COH(CF3)2
Et
propargyl



Ib278
CF2Cl
Et
propargyl



Ib279
CFCl2
Et
propargyl



Ib280
CCl3
Et
propargyl



Ib281
OCF3
Et
propargyl



Ib282
OCHF2
Et
propargyl



Ib283
OCF2CF3
Et
propargyl



Ib284
OCF2CHF2
Et
propargyl



Ib285
OCF(CF3)2
Et
propargyl



Ib286
OCF2Cl
Et
propargyl



Ib287
OCFCl2
Et
propargyl



Ib288
OCCl3
Et
propargyl



Ib289
CF3
Et
Me—CN



Ib290
CHF2
Et
Me—CN



Ib291
CF2CF3
Et
Me—CN



Ib292
CF(CF3)2
Et
Me—CN



Ib293
COH(CF3)2
Et
Me—CN



Ib294
CF2Cl
Et
Me—CN



Ib295
CFCl2
Et
Me—CN



Ib296
CCl3
Et
Me—CN



Ib297
OCF3
Et
Me—CN



Ib298
OCHF2
Et
Me—CN



Ib299
OCF2CF3
Et
Me—CN



Ib300
OCF2CHF2
Et
Me—CN



Ib301
OCF(CF3)2
Et
Me—CN



Ib302
OCF2Cl
Et
Me—CN



Ib303
OCFCl2
Et
Me—CN



Ib304
OCCl3
Et
Me—CN



Ib305
CF3
Pr
Pr



Ib306
CHF2
Pr
Pr



Ib307
CF2CF3
Pr
Pr



Ib308
CF(CF3)2
Pr
Pr



Ib309
COH(CF3)2
Pr
Pr



Ib310
CF2Cl
Pr
Pr



Ib311
CFCl2
Pr
Pr



Ib312
CCl3
Pr
Pr



Ib313
OCF3
Pr
Pr



Ib314
OCHF2
Pr
Pr



Ib315
OCF2CF3
Pr
Pr



Ib316
OCF2CHF2
Pr
Pr



Ib317
OCF(CF3)2
Pr
Pr



Ib318
OCF2Cl
Pr
Pr



Ib319
OCFCl2
Pr
Pr



Ib320
OCCl3
Pr
Pr



Ib321
CF3
Pr
iPr



Ib322
CHF2
Pr
iPr



Ib323
CF2CF3
Pr
iPr



Ib324
CF(CF3)2
Pr
iPr



Ib325
COH(CF3)2
Pr
iPr



Ib326
CF2Cl
Pr
iPr



Ib327
CFCl2
Pr
iPr



Ib328
CCl3
Pr
iPr



Ib329
OCF3
Pr
iPr



Ib330
OCHF2
Pr
iPr



Ib331
OCF2CF3
Pr
iPr



Ib332
OCF2CHF2
Pr
iPr



Ib333
OCF(CF3)2
Pr
iPr



Ib334
OCF2Cl
Pr
iPr



Ib335
OCFCl2
Pr
iPr



Ib336
OCCl3
Pr
iPr



Ib337
CF3
Pr
Bu



Ib338
CHF2
Pr
Bu



Ib339
CF2CF3
Pr
Bu



Ib340
CF(CF3)2
Pr
Bu



Ib341
COH(CF3)2
Pr
Bu



Ib342
CF2Cl
Pr
Bu



Ib343
CFCl2
Pr
Bu



Ib344
CCl3
Pr
Bu



Ib345
OCF3
Pr
Bu



Ib346
OCHF2
Pr
Bu



Ib347
OCF2CF3
Pr
Bu



Ib348
OCF2CHF2
Pr
Bu



Ib349
OCF(CF3)2
Pr
Bu



Ib350
OCF2Cl
Pr
Bu



Ib351
OCFCl2
Pr
Bu



Ib352
OCCl3
Pr
Bu



Ib353
CF3
Pr
Pn



Ib354
CHF2
Pr
Pn



Ib355
CF2CF3
Pr
Pn



Ib356
CF(CF3)2
Pr
Pn



Ib357
COH(CF3)2
Pr
Pn



Ib358
CF2Cl
Pr
Pn



Ib359
CFCl2
Pr
Pn



Ib360
CCl3
Pr
Pn



Ib361
OCF3
Pr
Pn



Ib362
OCHF2
Pr
Pn



Ib363
OCF2CF3
Pr
Pn



Ib364
OCF2CHF2
Pr
Pn



Ib365
OCF(CF3)2
Pr
Pn



Ib366
OCF2Cl
Pr
Pn



Ib367
OCFCl2
Pr
Pn



Ib368
OCCl3
Pr
Pn



Ib369
CF3
Pr
Me—cPr



Ib370
CHF2
Pr
Me—cPr



Ib371
CF2CF3
Pr
Me—cPr



Ib372
CF(CF3)2
Pr
Me—cPr



Ib373
COH(CF3)2
Pr
Me—cPr



Ib374
CF2Cl
Pr
Me—cPr



Ib375
CFCl2
Pr
Me—cPr



Ib376
CCl3
Pr
Me—cPr



Ib377
OCF3
Pr
Me—cPr



Ib378
OCHF2
Pr
Me—cPr



Ib379
OCF2CF3
Pr
Me—cPr



Ib380
OCF2CHF2
Pr
Me—cPr



Ib381
OCF(CF3)2
Pr
Me—cPr



Ib382
OCF2Cl
Pr
Me—cPr



Ib383
OCFCl2
Pr
Me—cPr



Ib384
OCCl3
Pr
Me—cPr



Ib385
CF3
Pr
allyl



Ib386
CHF2
Pr
allyl



Ib387
CF2CF3
Pr
allyl



Ib388
CF(CF3)2
Pr
allyl



Ib389
COH(CF3)2
Pr
allyl



Ib390
CF2Cl
Pr
allyl



Ib391
CFCl2
Pr
allyl



Ib392
CCl3
Pr
allyl



Ib393
OCF3
Pr
allyl



Ib394
OCHF2
Pr
allyl



Ib395
OCF2CF3
Pr
allyl



Ib396
OCF2CHF2
Pr
allyl



Ib397
OCF(CF3)2
Pr
allyl



Ib398
OCF2Cl
Pr
allyl



Ib399
OCFCl2
Pr
allyl



Ib400
OCCl3
Pr
allyl



Ib401
CF3
Pr
propargyl



Ib402
CHF2
Pr
propargyl



Ib403
CF2CF3
Pr
propargyl



Ib404
CF(CF3)2
Pr
propargyl



Ib405
COH(CF3)2
Pr
propargyl



Ib406
CF2Cl
Pr
propargyl



Ib407
CFCl2
Pr
propargyl



Ib408
CCl3
Pr
propargyl



Ib409
OCF3
Pr
propargyl



Ib410
OCHF2
Pr
propargyl



Ib411
OCF2CF3
Pr
propargyl



Ib412
OCF2CHF2
Pr
propargyl



Ib413
OCF(CF3)2
Pr
propargyl



Ib414
OCF2Cl
Pr
propargyl



Ib415
OCFCl2
Pr
propargyl



Ib416
OCCl3
Pr
propargyl



Ib417
CF3
Pr
Me—CN



Ib418
CHF2
Pr
Me—CN



Ib419
CF2CF3
Pr
Me—CN



Ib420
CF(CF3)2
Pr
Me—CN



Ib421
COH(CF3)2
Pr
Me—CN



Ib422
CF2Cl
Pr
Me—CN



Ib423
CFCl2
Pr
Me—CN



Ib424
CCl3
Pr
Me—CN



Ib425
OCF3
Pr
Me—CN



Ib426
OCHF2
Pr
Me—CN



Ib427
OCF2CF3
Pr
Me—CN



Ib428
OCF2CHF2
Pr
Me—CN



Ib429
OCF(CF3)2
Pr
Me—CN



Ib430
OCF2Cl
Pr
Me—CN



Ib431
OCFCl2
Pr
Me—CN



Ib432
OCCl3
Pr
Me—CN



Ib433
CF3
Pr
Pr



Ib434
CHF2
Pr
Pr



Ib435
CF2CF3
Pr
Pr



Ib436
CF(CF3)2
Pr
Pr



Ib437
COH(CF3)2
Pr
Pr



Ib438
CF2Cl
Pr
Pr



Ib439
CFCl2
Pr
Pr



Ib440
CCl3
Pr
Pr



Ib441
OCF3
Pr
Pr



Ib442
OCHF2
Pr
Pr



Ib443
OCF2CF3
Pr
Pr



Ib444
OCF2CHF2
Pr
Pr



Ib445
OCF(CF3)2
Pr
Pr



Ib446
OCF2Cl
Pr
Pr



Ib447
OCFCl2
Pr
Pr



Ib448
OCCl3
Pr
Pr



Ib449
CF3
Pr
iPr



Ib450
CHF2
Pr
iPr



Ib451
CF2CF3
Pr
iPr



Ib452
CF(CF3)2
Pr
iPr



Ib453
COH(CF3)2
Pr
iPr



Ib454
CF2Cl
Pr
iPr



Ib455
CFCl2
Pr
iPr



Ib456
CCl3
Pr
iPr



Ib457
OCF3
Pr
iPr



Ib458
OCHF2
Pr
iPr



Ib459
OCF2CF3
Pr
iPr



Ib460
OCF2CHF2
Pr
iPr



Ib461
OCF(CF3)2
Pr
iPr



Ib462
OCF2Cl
Pr
iPr



Ib463
OCFCl2
Pr
iPr



Ib464
OCCl3
Pr
iPr



Ib465
CF3
Pr
Bu



Ib466
CHF2
Pr
Bu



Ib467
CF2CF3
Pr
Bu



Ib468
CF(CF3)2
Pr
Bu



Ib469
COH(CF3)2
Pr
Bu



Ib470
CF2Cl
Pr
Bu



Ib471
CFCl2
Pr
Bu



Ib472
CCl3
Pr
Bu



Ib473
OCF3
Pr
Bu



Ib474
OCHF2
Pr
Bu



Ib475
OCF2CF3
Pr
Bu



Ib476
OCF2CHF2
Pr
Bu



Ib477
OCF(CF3)2
Pr
Bu



Ib478
OCF2Cl
Pr
Bu



Ib479
OCFCl2
Pr
Bu



Ib480
OCCl3
Pr
Bu



Ib481
CF3
Pr
Pn



Ib482
CHF2
Pr
Pn



Ib483
CF2CF3
Pr
Pn



Ib484
CF(CF3)2
Pr
Pn



Ib485
COH(CF3)2
Pr
Pn



Ib486
CF2Cl
Pr
Pn



Ib487
CFCl2
Pr
Pn



Ib488
CCl3
Pr
Pn



Ib489
OCF3
Pr
Pn



Ib490
OCHF2
Pr
Pn



Ib491
OCF2CF3
Pr
Pn



Ib492
OCF2CHF2
Pr
Pn



Ib493
OCF(CF3)2
Pr
Pn



Ib494
OCF2Cl
Pr
Pn



Ib495
OCFCl2
Pr
Pn



Ib496
OCCl3
Pr
Pn



Ib497
CF3
Pr
Me—cPr



Ib498
CHF2
Pr
Me—cPr



Ib499
CF2CF3
Pr
Me—cPr



Ib500
CF(CF3)2
Pr
Me—cPr



Ib501
COH(CF3)2
Pr
Me—cPr



Ib502
CF2Cl
Pr
Me—cPr



Ib503
CFCl2
Pr
Me—cPr



Ib504
CCl3
Pr
Me—cPr



Ib505
OCF3
Pr
Me—cPr



Ib506
OCHF2
Pr
Me—cPr



Ib507
OCF2CF3
Pr
Me—cPr



Ib508
OCF2CHF2
Pr
Me—cPr



Ib509
OCF(CF3)2
Pr
Me—cPr



Ib510
OCF2Cl
Pr
Me—cPr



Ib511
OCFCl2
Pr
Me—cPr



Ib512
OCCl3
Pr
Me—cPr



Ib513
CF3
Pr
allyl



Ib514
CHF2
Pr
allyl



Ib515
CF2CF3
Pr
allyl



Ib516
CF(CF3)2
Pr
allyl



Ib517
COH(CF3)2
Pr
allyl



Ib518
CF2Cl
Pr
allyl



Ib519
CFCl2
Pr
allyl



Ib520
CCl3
Pr
allyl



Ib521
OCF3
Pr
allyl



Ib522
OCHF2
Pr
allyl



Ib523
OCF2CF3
Pr
allyl



Ib524
OCF2CHF2
Pr
allyl



Ib525
OCF(CF3)2
Pr
allyl



Ib526
OCF2Cl
Pr
allyl



Ib527
OCFCl2
Pr
allyl



Ib528
OCCl3
Pr
allyl



Ib529
CF3
Pr
propargyl



Ib530
CHF2
Pr
propargyl



Ib531
CF2CF3
Pr
propargyl



Ib532
CF(CF3)2
Pr
propargyl



Ib533
COH(CF3)2
Pr
propargyl



Ib534
CF2Cl
Pr
propargyl



Ib535
CFCl2
Pr
propargyl



Ib536
CCl3
Pr
propargyl



Ib537
OCF3
Pr
propargyl



Ib538
OCHF2
Pr
propargyl



Ib539
OCF2CF3
Pr
propargyl



Ib540
OCF2CHF2
Pr
propargyl



Ib541
OCF(CF3)2
Pr
propargyl



Ib542
OCF2Cl
Pr
propargyl



Ib543
OCFCl2
Pr
propargyl



Ib544
OCCl3
Pr
propargyl



Ib545
CF3
Pr
Me—CN



Ib546
CHF2
Pr
Me—CN



Ib547
CF2CF3
Pr
Me—CN



Ib548
CF(CF3)2
Pr
Me—CN



Ib549
COH(CF3)2
Pr
Me—CN



Ib550
CF2Cl
Pr
Me—CN



Ib551
CFCl2
Pr
Me—CN



Ib552
CCl3
Pr
Me—CN



Ib553
OCF3
Pr
Me—CN



Ib554
OCHF2
Pr
Me—CN



Ib555
OCF2CF3
Pr
Me—CN



Ib556
OCF2CHF2
Pr
Me—CN



Ib557
OCF(CF3)2
Pr
Me—CN



Ib558
OCF2Cl
Pr
Me—CN



Ib559
OCFCl2
Pr
Me—CN



Ib560
OCCl3
Pr
Me—CN



Ib561
CF3
iPr
iPr



Ib562
CHF2
iPr
iPr



Ib563
CF2CF3
iPr
iPr



Ib564
CF(CF3)2
iPr
iPr



Ib565
COH(CF3)2
iPr
iPr



Ib566
CF2Cl
iPr
iPr



Ib567
CFCl2
iPr
iPr



Ib568
CCl3
iPr
iPr



Ib569
OCF3
iPr
iPr



Ib570
OCHF2
iPr
iPr



Ib571
OCF2CF3
iPr
iPr



Ib572
OCF2CHF2
iPr
iPr



Ib573
OCF(CF3)2
iPr
iPr



Ib574
OCF2Cl
iPr
iPr



Ib575
OCFCl2
iPr
iPr



Ib576
OCCl3
iPr
iPr



Ib577
CF3
iPr
Bu



Ib578
CHF2
iPr
Bu



Ib579
CF2CF3
iPr
Bu



Ib580
CF(CF3)2
iPr
Bu



Ib581
COH(CF3)2
iPr
Bu



Ib582
CF2Cl
iPr
Bu



Ib583
CFCl2
iPr
Bu



Ib584
CCl3
iPr
Bu



Ib585
OCF3
iPr
Bu



Ib586
OCHF2
iPr
Bu



Ib587
OCF2CF3
iPr
Bu



Ib588
OCF2CHF2
iPr
Bu



Ib589
OCF(CF3)2
iPr
Bu



Ib590
OCF2Cl
iPr
Bu



Ib591
OCFCl2
iPr
Bu



Ib592
OCCl3
iPr
Bu



Ib593
CF3
iPr
Pn



Ib594
CHF2
iPr
Pn



Ib595
CF2CF3
iPr
Pn



Ib596
CF(CF3)2
iPr
Pn



Ib597
COH(CF3)2
iPr
Pn



Ib598
CF2Cl
iPr
Pn



Ib599
CFCl2
iPr
Pn



Ib600
CCl3
iPr
Pn



Ib601
OCF3
iPr
Pn



Ib602
OCHF2
iPr
Pn



Ib603
OCF2CF3
iPr
Pn



Ib604
OCF2CHF2
iPr
Pn



Ib605
OCF(CF3)2
iPr
Pn



Ib606
OCF2Cl
iPr
Pn



Ib607
OCFCl2
iPr
Pn



Ib608
OCCl3
iPr
Pn



Ib609
CF3
iPr
Me—cPr



Ib610
CHF2
iPr
Me—cPr



Ib611
CF2CF3
iPr
Me—cPr



Ib612
CF(CF3)2
iPr
Me—cPr



Ib613
COH(CF3)2
iPr
Me—cPr



Ib614
CF2Cl
iPr
Me—cPr



Ib615
CFCl2
iPr
Me—cPr



Ib616
CCl3
iPr
Me—cPr



Ib617
OCF3
iPr
Me—cPr



Ib618
OCHF2
iPr
Me—cPr



Ib619
OCF2CF3
iPr
Me—cPr



Ib620
OCF2CHF2
iPr
Me—cPr



Ib621
OCF(CF3)2
iPr
Me—cPr



Ib622
OCF2Cl
iPr
Me—cPr



Ib623
OCFCl2
iPr
Me—cPr



Ib624
OCCl3
iPr
Me—cPr



Ib625
CF3
iPr
allyl



Ib626
CHF2
iPr
allyl



Ib627
CF2CF3
iPr
allyl



Ib628
CF(CF3)2
iPr
allyl



Ib629
COH(CF3)2
iPr
allyl



Ib630
CF2Cl
iPr
allyl



Ib631
CFCl2
iPr
allyl



Ib632
CCl3
iPr
allyl



Ib633
OCF3
iPr
allyl



Ib634
OCHF2
iPr
allyl



Ib635
OCF2CF3
iPr
allyl



Ib636
OCF2CHF2
iPr
allyl



Ib637
OCF(CF3)2
iPr
allyl



Ib638
OCF2Cl
iPr
allyl



Ib639
OCFCl2
iPr
allyl



Ib640
OCCl3
iPr
allyl



Ib641
CF3
iPr
propargyl



Ib642
CHF2
iPr
propargyl



Ib643
CF2CF3
iPr
propargyl



Ib644
CF(CF3)2
iPr
propargyl



Ib645
COH(CF3)2
iPr
propargyl



Ib646
CF2Cl
iPr
propargyl



Ib647
CFCl2
iPr
propargyl



Ib648
CCl3
iPr
propargyl



Ib649
OCF3
iPr
propargyl



Ib650
OCHF2
iPr
propargyl



Ib651
OCF2CF3
iPr
propargyl



Ib652
OCF2CHF2
iPr
propargyl



Ib653
OCF(CF3)2
iPr
propargyl



Ib654
OCF2Cl
iPr
propargyl



Ib655
OCFCl2
iPr
propargyl



Ib656
OCCl3
iPr
propargyl



Ib657
CF3
iPr
Me—CN



Ib658
CHF2
iPr
Me—CN



Ib659
CF2CF3
iPr
Me—CN



Ib660
CF(CF3)2
iPr
Me—CN



Ib661
COH(CF3)2
iPr
Me—CN



Ib662
CF2Cl
iPr
Me—CN



Ib663
CFCl2
iPr
Me—CN



Ib664
CCl3
iPr
Me—CN



Ib665
OCF3
iPr
Me—CN



Ib666
OCHF2
iPr
Me—CN



Ib667
OCF2CF3
iPr
Me—CN



Ib668
OCF2CHF2
iPr
Me—CN



Ib669
OCF(CF3)2
iPr
Me—CN



Ib670
OCF2Cl
iPr
Me—CN



Ib671
OCFCl2
iPr
Me—CN



Ib672
OCCl3
iPr
Me—CN



Ib673
CF3
Bu
Bu



Ib674
CHF2
Bu
Bu



Ib675
CF2CF3
Bu
Bu



Ib676
CF(CF3)2
Bu
Bu



Ib677
COH(CF3)2
Bu
Bu



Ib678
CF2Cl
Bu
Bu



Ib679
CFCl2
Bu
Bu



Ib680
CCl3
Bu
Bu



Ib681
OCF3
Bu
Bu



Ib682
OCHF2
Bu
Bu



Ib683
OCF2CF3
Bu
Bu



Ib684
OCF2CHF2
Bu
Bu



Ib685
OCF(CF3)2
Bu
Bu



Ib686
OCF2Cl
Bu
Bu



Ib687
OCFCl2
Bu
Bu



Ib688
OCCl3
Bu
Bu



Ib689
CF3
Bu
Pn



Ib690
CHF2
Bu
Pn



Ib691
CF2CF3
Bu
Pn



Ib692
CF(CF3)2
Bu
Pn



Ib693
COH(CF3)2
Bu
Pn



Ib694
CF2Cl
Bu
Pn



Ib695
CFCl2
Bu
Pn



Ib696
CCl3
Bu
Pn



Ib697
OCF3
Bu
Pn



Ib698
OCHF2
Bu
Pn



Ib699
OCF2CF3
Bu
Pn



Ib700
OCF2CHF2
Bu
Pn



Ib701
OCF(CF3)2
Bu
Pn



Ib702
OCF2Cl
Bu
Pn



Ib703
OCFCl2
Bu
Pn



Ib704
OCCl3
Bu
Pn



Ib705
CF3
Bu
Me—cPr



Ib706
CHF2
Bu
Me—cPr



Ib707
CF2CF3
Bu
Me—cPr



Ib708
CF(CF3)2
Bu
Me—cPr



Ib709
COH(CF3)2
Bu
Me—cPr



Ib710
CF2Cl
Bu
Me—cPr



Ib711
CFCl2
Bu
Me—cPr



Ib712
CCl3
Bu
Me—cPr



Ib713
OCF3
Bu
Me—cPr



Ib714
OCHF2
Bu
Me—cPr



Ib715
OCF2CF3
Bu
Me—cPr



Ib716
OCF2CHF2
Bu
Me—cPr



Ib717
OCF(CF3)2
Bu
Me—cPr



Ib718
OCF2Cl
Bu
Me—cPr



Ib719
OCFCl2
Bu
Me—cPr



Ib720
OCCl3
Bu
Me—cPr



Ib721
CF3
Bu
allyl



Ib722
CHF2
Bu
allyl



Ib723
CF2CF3
Bu
allyl



Ib724
CF(CF3)2
Bu
allyl



Ib725
COH(CF3)2
Bu
allyl



Ib726
CF2Cl
Bu
allyl



Ib727
CFCl2
Bu
allyl



Ib728
CCl3
Bu
allyl



Ib729
OCF3
Bu
allyl



Ib730
OCHF2
Bu
allyl



Ib731
OCF2CF3
Bu
allyl



Ib732
OCF2CHF2
Bu
allyl



Ib733
OCF(CF3)2
Bu
allyl



Ib734
OCF2Cl
Bu
allyl



Ib735
OCFCl2
Bu
allyl



Ib736
OCCl3
Bu
allyl



Ib737
CF3
Bu
propargyl



Ib738
CHF2
Bu
propargyl



Ib739
CF2CF3
Bu
propargyl



Ib740
CF(CF3)2
Bu
propargyl



Ib741
COH(CF3)2
Bu
propargyl



Ib742
CF2Cl
Bu
propargyl



Ib743
CFCl2
Bu
propargyl



Ib744
CCl3
Bu
propargyl



Ib745
OCF3
Bu
propargyl



Ib746
OCHF2
Bu
propargyl



Ib747
OCF2CF3
Bu
propargyl



Ib748
OCF2CHF2
Bu
propargyl



Ib749
OCF(CF3)2
Bu
propargyl



Ib750
OCF2Cl
Bu
propargyl



Ib751
OCFCl2
Bu
propargyl



Ib752
OCCl3
Bu
propargyl



Ib753
CF3
Bu
Me—CN



Ib754
CHF2
Bu
Me—CN



Ib755
CF2CF3
Bu
Me—CN



Ib756
CF(CF3)2
Bu
Me—CN



Ib757
COH(CF3)2
Bu
Me—CN



Ib758
CF2Cl
Bu
Me—CN



Ib759
CFCl2
Bu
Me—CN



Ib760
CCl3
Bu
Me—CN



Ib761
OCF3
Bu
Me—CN



Ib762
OCHF2
Bu
Me—CN



Ib763
OCF2CF3
Bu
Me—CN



Ib764
OCF2CHF2
Bu
Me—CN



Ib765
OCF(CF3)2
Bu
Me—CN



Ib766
OCF2Cl
Bu
Me—CN



Ib767
OCFCl2
Bu
Me—CN



Ib768
OCCl3
Bu
Me—CN



Ib769
CF3
Pn
Pn



Ib770
CHF2
Pn
Pn



Ib771
CF2CF3
Pn
Pn



Ib772
CF(CF3)2
Pn
Pn



Ib773
COH(CF3)2
Pn
Pn



Ib774
CF2Cl
Pn
Pn



Ib775
CFCl2
Pn
Pn



Ib776
CCl3
Pn
Pn



Ib777
OCF3
Pn
Pn



Ib778
OCHF2
Pn
Pn



Ib779
OCF2CF3
Pn
Pn



Ib780
OCF2CHF2
Pn
Pn



Ib781
OCF(CF3)2
Pn
Pn



Ib782
OCF2Cl
Pn
Pn



Ib783
OCFCl2
Pn
Pn



Ib784
OCCl3
Pn
Pn



Ib785
CF3
Pn
Me—cPr



Ib786
CHF2
Pn
Me—cPr



Ib787
CF2CF3
Pn
Me—cPr



Ib788
CF(CF3)2
Pn
Me—cPr



Ib789
COH(CF3)2
Pn
Me—cPr



Ib790
CF2Cl
Pn
Me—cPr



Ib791
CFCl2
Pn
Me—cPr



Ib792
CCl3
Pn
Me—cPr



Ib793
OCF3
Pn
Me—cPr



Ib794
OCHF2
Pn
Me—cPr



Ib795
OCF2CF3
Pn
Me—cPr



Ib796
OCF2CHF2
Pn
Me—cPr



Ib797
OCF(CF3)2
Pn
Me—cPr



Ib798
OCF2Cl
Pn
Me—cPr



Ib799
OCFCl2
Pn
Me—cPr



Ib800
OCCl3
Pn
Me—cPr



Ib801
CF3
Pn
allyl



Ib802
CHF2
Pn
allyl



Ib803
CF2CF3
Pn
allyl



Ib804
CF(CF3)2
Pn
allyl



Ib805
COH(CF3)2
Pn
allyl



Ib806
CF2Cl
Pn
allyl



Ib807
CFCl2
Pn
allyl



Ib808
CCl3
Pn
allyl



Ib809
OCF3
Pn
allyl



Ib810
OCHF2
Pn
allyl



Ib811
OCF2CF3
Pn
allyl



Ib812
OCF2CHF2
Pn
allyl



Ib813
OCF(CF3)2
Pn
allyl



Ib814
OCF2Cl
Pn
allyl



Ib815
OCFCl2
Pn
allyl



Ib816
OCCl3
Pn
allyl



Ib817
CF3
Pn
propargyl



Ib818
CHF2
Pn
propargyl



Ib819
CF2CF3
Pn
propargyl



Ib820
CF(CF3)2
Pn
propargyl



Ib821
COH(CF3)2
Pn
propargyl



Ib822
CF2Cl
Pn
propargyl



Ib823
CFCl2
Pn
propargyl



Ib824
CCl3
Pn
propargyl



Ib825
OCF3
Pn
propargyl



Ib826
OCHF2
Pn
propargyl



Ib827
OCF2CF3
Pn
propargyl



Ib828
OCF2CHF2
Pn
propargyl



Ib829
OCF(CF3)2
Pn
propargyl



Ib830
OCF2Cl
Pn
propargyl



Ib831
OCFCl2
Pn
propargyl



Ib832
OCCl3
Pn
propargyl



Ib833
CF3
Pn
Me—CN



Ib834
CHF2
Pn
Me—CN



Ib835
CF2CF3
Pn
Me—CN



Ib836
CF(CF3)2
Pn
Me—CN



Ib837
COH(CF3)2
Pn
Me—CN



Ib838
CF2Cl
Pn
Me—CN



Ib839
CFCl2
Pn
Me—CN



Ib840
CCl3
Pn
Me—CN



Ib841
OCF3
Pn
Me—CN



Ib842
OCHF2
Pn
Me—CN



Ib843
OCF2CF3
Pn
Me—CN



Ib844
OCF2CHF2
Pn
Me—CN



Ib845
OCF(CF3)2
Pn
Me—CN



Ib846
OCF2Cl
Pn
Me—CN



Ib847
OCFCl2
Pn
Me—CN



Ib848
OCCl3
Pn
Me—CN



Ib849
CF3
Me—cPr
Me—cPr



Ib850
CHF2
Me—cPr
Me—cPr



Ib851
CF2CF3
Me—cPr
Me—cPr



Ib852
CF(CF3)2
Me—cPr
Me—cPr



Ib853
COH(CF3)2
Me—cPr
Me—cPr



Ib854
CF2Cl
Me—cPr
Me—cPr



Ib855
CFCl2
Me—cPr
Me—cPr



Ib856
CCl3
Me—cPr
Me—cPr



Ib857
OCF3
Me—cPr
Me—cPr



Ib858
OCHF2
Me—cPr
Me—cPr



Ib859
OCF2CF3
Me—cPr
Me—cPr



Ib860
OCF2CHF2
Me—cPr
Me—cPr



Ib861
OCF(CF3)2
Me—cPr
Me—cPr



Ib862
OCF2Cl
Me—cPr
Me—cPr



Ib863
OCFCl2
Me—cPr
Me—cPr



Ib864
OCCl3
Me—cPr
Me—cPr



Ib865
CF3
Me—cPr
allyl



Ib866
CHF2
Me—cPr
allyl



Ib867
CF2CF3
Me—cPr
allyl



Ib868
CF(CF3)2
Me—cPr
allyl



Ib869
COH(CF3)2
Me—cPr
allyl



Ib870
CF2Cl
Me—cPr
allyl



Ib871
CFCl2
Me—cPr
allyl



Ib872
CCl3
Me—cPr
allyl



Ib873
OCF3
Me—cPr
allyl



Ib874
OCHF2
Me—cPr
allyl



Ib875
OCF2CF3
Me—cPr
allyl



Ib876
OCF2CHF2
Me—cPr
allyl



Ib877
OCF(CF3)2
Me—cPr
allyl



Ib878
OCF2Cl
Me—cPr
allyl



Ib879
OCFCl2
Me—cPr
allyl



Ib880
OCCl3
Me—cPr
allyl



Ib881
CF3
Me—cPr
propargyl



Ib882
CHF2
Me—cPr
propargyl



Ib883
CF2CF3
Me—cPr
propargyl



Ib884
CF(CF3)2
Me—cPr
propargyl



Ib885
COH(CF3)2
Me—cPr
propargyl



Ib886
CF2Cl
Me—cPr
propargyl



Ib887
CFCl2
Me—cPr
propargyl



Ib888
CCl3
Me—cPr
propargyl



Ib889
OCF3
Me—cPr
propargyl



Ib890
OCHF2
Me—cPr
propargyl



Ib891
OCF2CF3
Me—cPr
propargyl



Ib892
OCF2CHF2
Me—cPr
propargyl



Ib893
OCF(CF3)2
Me—cPr
propargyl



Ib894
OCF2Cl
Me—cPr
propargyl



Ib895
OCFCl2
Me—cPr
propargyl



Ib896
OCCl3
Me—cPr
propargyl



Ib897
CF3
Me—cPr
Me—CN



Ib898
CHF2
Me—cPr
Me—CN



Ib899
CF2CF3
Me—cPr
Me—CN



Ib900
CF(CF3)2
Me—cPr
Me—CN



Ib901
COH(CF3)2
Me—cPr
Me—CN



Ib902
CF2Cl
Me—cPr
Me—CN



Ib903
CFCl2
Me—cPr
Me—CN



Ib904
CCl3
Me—cPr
Me—CN



Ib905
OCF3
Me—cPr
Me—CN



Ib906
OCHF2
Me—cPr
Me—CN



Ib907
OCF2CF3
Me—cPr
Me—CN



Ib908
OCF2CHF2
Me—cPr
Me—CN



Ib909
OCF(CF3)2
Me—cPr
Me—CN



Ib910
OCF2Cl
Me—cPr
Me—CN



Ib911
OCFCl2
Me—cPr
Me—CN



Ib912
OCCl3
Me—cPr
Me—CN



Ib913
CF3
allyl
allyl



Ib914
CHF2
allyl
allyl



Ib915
CF2CF3
allyl
allyl



Ib916
CF(CF3)2
allyl
allyl



Ib917
COH(CF3)2
allyl
allyl



Ib918
CF2Cl
allyl
allyl



Ib919
CFCl2
allyl
allyl



Ib920
CCl3
allyl
allyl



Ib921
OCF3
allyl
allyl



Ib922
OCHF2
allyl
allyl



Ib923
OCF2CF3
allyl
allyl



Ib924
OCF2CHF2
allyl
allyl



Ib925
OCF(CF3)2
allyl
allyl



Ib926
OCF2Cl
allyl
allyl



Ib927
OCFCl2
allyl
allyl



Ib928
OCCl3
allyl
allyl



Ib929
CF3
allyl
propargyl



Ib930
CHF2
allyl
propargyl



Ib931
CF2CF3
allyl
propargyl



Ib932
CF(CF3)2
allyl
propargyl



Ib933
COH(CF3)2
allyl
propargyl



Ib934
CF2Cl
allyl
propargyl



Ib935
CFCl2
allyl
propargyl



Ib936
CCl3
allyl
propargyl



Ib937
OCF3
allyl
propargyl



Ib938
OCHF2
allyl
propargyl



Ib939
OCF2CF3
allyl
propargyl



Ib940
OCF2CHF2
allyl
propargyl



Ib941
OCF(CF3)2
allyl
propargyl



Ib942
OCF2Cl
allyl
propargyl



Ib943
OCFCl2
allyl
propargyl



Ib944
OCCl3
allyl
propargyl



Ib945
CF3
allyl
Me—CN



Ib946
CHF2
allyl
Me—CN



Ib947
CF2CF3
allyl
Me—CN



Ib948
CF(CF3)2
allyl
Me—CN



Ib949
COH(CF3)2
allyl
Me—CN



Ib950
CF2Cl
allyl
Me—CN



Ib951
CFCl2
allyl
Me—CN



Ib952
CCl3
allyl
Me—CN



Ib953
OCF3
allyl
Me—CN



Ib954
OCHF2
allyl
Me—CN



Ib955
OCF2CF3
allyl
Me—CN



Ib956
OCF2CHF2
allyl
Me—CN



Ib957
OCF(CF3)2
allyl
Me—CN



Ib958
OCF2Cl
allyl
Me—CN



Ib959
OCFCl2
allyl
Me—CN



Ib960
OCCl3
allyl
Me—CN



Ib961
CF3
propargyl
propargyl



Ib962
CHF2
propargyl
propargyl



Ib963
CF2CF3
propargyl
propargyl



Ib964
CF(CF3)2
propargyl
propargyl



Ib965
COH(CF3)2
propargyl
propargyl



Ib966
CF2Cl
propargyl
propargyl



Ib967
CFCl2
propargyl
propargyl



Ib968
CCl3
propargyl
propargyl



Ib969
OCF3
propargyl
propargyl



Ib970
OCHF2
propargyl
propargyl



Ib971
OCF2CF3
propargyl
propargyl



Ib972
OCF2CHF2
propargyl
propargyl



Ib973
OCF(CF3)2
propargyl
propargyl



Ib974
OCF2Cl
propargyl
propargyl



Ib975
OCFCl2
propargyl
propargyl



Ib976
OCCl3
propargyl
propargyl



Ib977
CF3
propargyl
Me—CN



Ib978
CHF2
propargyl
Me—CN



Ib979
CF2CF3
propargyl
Me—CN



Ib980
CF(CF3)2
propargyl
Me—CN



Ib981
COH(CF3)2
propargyl
Me—CN



Ib982
CF2Cl
propargyl
Me—CN



Ib983
CFCl2
propargyl
Me—CN



Ib984
CCl3
propargyl
Me—CN



Ib985
OCF3
propargyl
Me—CN



Ib986
OCHF2
propargyl
Me—CN



Ib987
OCF2CF3
propargyl
Me—CN



Ib988
OCF2CHF2
propargyl
Me—CN



Ib989
OCF(CF3)2
propargyl
Me—CN



Ib990
OCF2Cl
propargyl
Me—CN



Ib991
OCFCl2
propargyl
Me—CN



Ib992
OCCl3
propargyl
Me—CN



Ib993
CF3
Me—CN
Me—CN



Ib994
CHF2
Me—CN
Me—CN



Ib995
CF2CF3
Me—CN
Me—CN



Ib996
CF(CF3)2
Me—CN
Me—CN



Ib997
COH(CF3)2
Me—CN
Me—CN



Ib998
CF2Cl
Me—CN
Me—CN



Ib999
CFCl2
Me—CN
Me—CN



Ib1000
CCl3
Me—CN
Me—CN



Ib1001
OCF3
Me—CN
Me—CN



Ib1002
OCHF2
Me—CN
Me—CN



Ib1003
OCF2CF3
Me—CN
Me—CN



Ib1004
OCF2CHF2
Me—CN
Me—CN



Ib1005
OCF(CF3)2
Me—CN
Me—CN



Ib1006
OCF2Cl
Me—CN
Me—CN



Ib1007
OCFCl2
Me—CN
Me—CN



Ib1008
OCCl3
Me—CN
Me—CN



Ib1009
CF3
H
Me



Ib1010
CHF2
H
Me



Ib1011
CF2CF3
H
Me



Ib1012
CF(CF3)2
H
Me



Ib1013
COH(CF3)2
H
Me



Ib1014
CF2Cl
H
Me



Ib1015
CFCl2
H
Me



Ib1016
CCl3
H
Me



Ib1017
OCF3
H
Me



Ib1018
OCHF2
H
Me



Ib1019
OCF2CF3
H
Me



Ib1020
OCF2CHF2
H
Me



Ib1021
OCF(CF3)2
H
Me



Ib1022
OCF2Cl
H
Me



Ib1023
OCFCl2
H
Me



Ib1024
OCCl3
H
Me



Ib1025
CF3
H
Et



Ib1026
CHF2
H
Et



Ib1027
CF2CF3
H
Et



Ib1028
CF(CF3)2
H
Et



Ib1029
COH(CF3)2
H
Et



Ib1030
CF2Cl
H
Et



Ib1031
CFCl2
H
Et



Ib1032
CCl3
H
Et



Ib1033
OCF3
H
Et



Ib1034
OCHF2
H
Et



Ib1035
OCF2CF3
H
Et



Ib1036
OCF2CHF2
H
Et



Ib1037
OCF(CF3)2
H
Et



Ib1038
OCF2Cl
H
Et



Ib1039
OCFCl2
H
Et



Ib1040
OCCl3
H
Et



Ib1041
CF3
H
Pr



Ib1042
CHF2
H
Pr



Ib1043
CF2CF3
H
Pr



Ib1044
CF(CF3)2
H
Pr



Ib1045
COH(CF3)2
H
Pr



Ib1046
CF2Cl
H
Pr



Ib1047
CFCl2
H
Pr



Ib1048
CCl3
H
Pr



Ib1049
OCF3
H
Pr



Ib1050
OCHF2
H
Pr



Ib1051
OCF2CF3
H
Pr



Ib1052
OCF2CHF2
H
Pr



Ib1053
OCF(CF3)2
H
Pr



Ib1054
OCF2Cl
H
Pr



Ib1055
OCFCl2
H
Pr



Ib1056
OCCl3
H
Pr



Ib1057
CF3
H
iPr



Ib1058
CHF2
H
iPr



Ib1059
CF2CF3
H
iPr



Ib1060
CF(CF3)2
H
iPr



Ib1061
COH(CF3)2
H
iPr



Ib1062
CF2Cl
H
iPr



Ib1063
CFCl2
H
iPr



Ib1064
CCl3
H
iPr



Ib1065
OCF3
H
iPr



Ib1066
OCHF2
H
iPr



Ib1067
OCF2CF3
H
iPr



Ib1068
OCF2CHF2
H
iPr



Ib1069
OCF(CF3)2
H
iPr



Ib1070
OCF2Cl
H
iPr



Ib1071
OCFCl2
H
iPr



Ib1072
OCCl3
H
iPr



Ib1073
CF3
H
Bu



Ib1074
CHF2
H
Bu



Ib1075
CF2CF3
H
Bu



Ib1076
CF(CF3)2
H
Bu



Ib1077
COH(CF3)2
H
Bu



Ib1078
CF2Cl
H
Bu



Ib1079
CFCl2
H
Bu



Ib1080
CCl3
H
Bu



Ib1081
OCF3
H
Bu



Ib1082
OCHF2
H
Bu



Ib1083
OCF2CF3
H
Bu



Ib1084
OCF2CHF2
H
Bu



Ib1085
OCF(CF3)2
H
Bu



Ib1086
OCF2Cl
H
Bu



Ib1087
OCFCl2
H
Bu



Ib1088
OCCl3
H
Bu



Ib1089
CF3
H
Pn



Ib1090
CHF2
H
Pn



Ib1091
CF2CF3
H
Pn



Ib1092
CF(CF3)2
H
Pn



Ib1093
COH(CF3)2
H
Pn



Ib1094
CF2Cl
H
Pn



Ib1095
CFCl2
H
Pn



Ib1096
CCl3
H
Pn



Ib1097
OCF3
H
Pn



Ib1098
OCHF2
H
Pn



Ib1099
OCF2CF3
H
Pn



Ib1100
OCF2CHF2
H
Pn



Ib1101
OCF(CF3)2
H
Pn



Ib1102
OCF2Cl
H
Pn



Ib1103
OCFCl2
H
Pn



Ib1104
OCCl3
H
Pn



Ib1105
CF3
H
Me—cPr



Ib1106
CHF2
H
Me—cPr



Ib1107
CF2CF3
H
Me—cPr



Ib1108
CF(CF3)2
H
Me—cPr



Ib1109
COH(CF3)2
H
Me—cPr



Ib1110
CF2Cl
H
Me—cPr



Ib1111
CFCl2
H
Me—cPr



Ib1112
CCl3
H
Me—cPr



Ib1113
OCF3
H
Me—cPr



Ib1114
OCHF2
H
Me—cPr



Ib1115
OCF2CF3
H
Me—cPr



Ib1116
OCF2CHF2
H
Me—cPr



Ib1117
OCF(CF3)2
H
Me—cPr



Ib1118
OCF2Cl
H
Me—cPr



Ib1119
OCFCl2
H
Me—cPr



Ib1120
OCCl3
H
Me—cPr



Ib1121
CF3
H
allyl



Ib1122
CHF2
H
allyl



Ib1123
CF2CF3
H
allyl



Ib1124
CF(CF3)2
H
allyl



Ib1125
COH(CF3)2
H
allyl



Ib1126
CF2Cl
H
allyl



Ib1127
CFCl2
H
allyl



Ib1128
CCl3
H
allyl



Ib1129
OCF3
H
allyl



Ib1130
OCHF2
H
allyl



Ib1131
OCF2CF3
H
allyl



Ib1132
OCF2CHF2
H
allyl



Ib1133
OCF(CF3)2
H
allyl



Ib1134
OCF2Cl
H
allyl



Ib1135
OCFCl2
H
allyl



Ib1136
OCCl3
H
allyl



Ib1137
CF3
H
propargyl



Ib1138
CHF2
H
propargyl



Ib1139
CF2CF3
H
propargyl



Ib1140
CF(CF3)2
H
propargyl



Ib1141
COH(CF3)2
H
propargyl



Ib1142
CF2Cl
H
propargyl



Ib1143
CFCl2
H
propargyl



Ib1144
CCl3
H
propargyl



Ib1145
OCF3
H
propargyl



Ib1146
OCHF2
H
propargyl



Ib1147
OCF2CF3
H
propargyl



Ib1148
OCF2CHF2
H
propargyl



Ib1149
OCF(CF3)2
H
propargyl



Ib1150
OCF2Cl
H
propargyl



Ib1151
OCFCl2
H
propargyl



Ib1152
OCCl3
H
propargyl



Ib1153
CF3
H
Me—CN



Ib1154
CHF2
H
Me—CN



Ib1155
CF2CF3
H
Me—CN



Ib1156
CF(CF3)2
H
Me—CN



Ib1157
COH(CF3)2
H
Me—CN



Ib1158
CF2Cl
H
Me—CN



Ib1159
CFCl2
H
Me—CN



Ib1160
CCl3
H
Me—CN



Ib1161
OCF3
H
Me—CN



Ib1162
OCHF2
H
Me—CN



Ib1163
OCF2CF3
H
Me—CN



Ib1164
OCF2CHF2
H
Me—CN



Ib1165
OCF(CF3)2
H
Me—CN



Ib1166
OCF2Cl
H
Me—CN



Ib1167
OCFCl2
H
Me—CN



Ib1168
OCCl3
H
Me—CN










Following annotation when used in the text are defined as follows:

    Me is methyl or —CH3;
    Et is ethyl or —CH2CH3;
    Pr is propyl or —(CH2)2CH3,
    iPr is isopropyl or —CH(CH3)2;
    Bu is butyl or (CH2)3CH3;
    Pn is pentyl or (CH2)4CH3;
    Me-cPr is methylcyclopropyl;
    Me-CN is cyanomethyl.


Examples of compounds of this particular preferred embodiment of such compounds are the compounds I-a given in the following tables 1 to 13.
Table 1 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is H and the remaining variables R1, R2, R5b band A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 2 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is F and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 3 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is Cl and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 4 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is Br and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 5 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is I and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 6 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is CN and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 7 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is NO2 and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 8 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is CH3 and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 9 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is CF3 and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 10 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is CHF2 and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 11 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is OCF3 and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 12 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is OCHF2 and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Table 13 Compounds of the formula I-a and their salts, wherein R5c and R5d are hydrogen, R5a is SCF3 and the remaining variables R1, R2, R5b and A correspond to each combination of the radicals numbered A1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.
Each example of the compounds of formula I-a as defined in the tables 1 to 13 constitutes a preferred embodiment of the invention.
Especially preferred embodiment of the invention are the compounds I-a wherein R5a, is hydrogen, A2, A3, A4 are CH, and the remaining variables R1, R2, R3, R4, R5b, A1 are defined in each row of the following Table D (variables R1, R2, R3, R4, R5b, A1 are defined in radical A and Ib being respectively defined in table B and C):










TABLE D







Radical A
Ib









A1a1
Ib1



A1a2
Ib1



A1a3
Ib1



A1a4
Ib1



A1a5
Ib1



A1a6
Ib1



A1a7
Ib1



A1a8
Ib1



A1a9
Ib1



A1a10
Ib1



A1a11
Ib1



A1a12
Ib1



A1a13
Ib1



A1a14
Ib1



A1a1
Ib17



A1a2
Ib17



A1a3
Ib17



A1a4
Ib17



A1a5
Ib17



A1a6
Ib17



A1a7
Ib17



A1a8
Ib17



A1a9
Ib17



A1a10
Ib17



A1a11
Ib17



A1a12
Ib17



A1a13
Ib17



A1a14
Ib17



A1a1
Ib33



A1a2
Ib33



A1a3
Ib33



A1a4
Ib33



A1a5
Ib33



A1a6
Ib33



A1a7
Ib33



A1a8
Ib33



A1a9
Ib33



A1a10
Ib33



A1a11
Ib33



A1a12
Ib33



A1a13
Ib33



A1a14
Ib33



A1a1
Ib49



A1a2
Ib49



A1a3
Ib49



A1a4
Ib49



A1a5
Ib49



A1a6
Ib49



A1a7
Ib49



A1a8
Ib49



A1a9
Ib49



A1a10
Ib49



A1a11
Ib49



A1a12
Ib49



A1a13
Ib49



A1a14
Ib49



A1a1
Ib65



A1a2
Ib65



A1a3
Ib65



A1a4
Ib65



A1a5
Ib65



A1a6
Ib65



A1a7
Ib65



A1a8
Ib65



A1a9
Ib65



A1a10
Ib65



A1a11
Ib65



A1a12
Ib65



A1a13
Ib65



A1a14
Ib65



A1a1
Ib81



A1a2
Ib81



A1a3
Ib81



A1a4
Ib81



A1a5
Ib81



A1a6
Ib81



A1a7
Ib81



A1a8
Ib81



A1a9
Ib81



A1a10
Ib81



A1a11
Ib81



A1a12
Ib81



A1a13
Ib81



A1a14
Ib81



A1a1
Ib97



A1a2
Ib97



A1a3
Ib97



A1a4
Ib97



A1a5
Ib97



A1a6
Ib97



A1a7
Ib97



A1a8
Ib97



A1a9
Ib97



A1a10
Ib97



A1a11
Ib97



A1a12
Ib97



A1a13
Ib97



A1a14
Ib97



A1a1
Ib113



A1a2
Ib113



A1a3
Ib113



A1a4
Ib113



A1a5
Ib113



A1a6
Ib113



A1a7
Ib113



A1a8
Ib113



A1a9
Ib113



A1a10
Ib113



A1a11
Ib113



A1a12
Ib113



A1a13
Ib113



A1a14
Ib113



A1a1
Ib129



A1a2
Ib129



A1a3
Ib129



A1a4
Ib129



A1a5
Ib129



A1a6
Ib129



A1a7
Ib129



A1a8
Ib129



A1a9
Ib129



A1a10
Ib129



A1a11
Ib129



A1a12
Ib129



A1a13
Ib129



A1a14
Ib129



A1a1
Ib145



A1a2
Ib145



A1a3
Ib145



A1a4
Ib145



A1a5
Ib145



A1a6
Ib145



A1a7
Ib145



A1a8
Ib145



A1a9
Ib145



A1a10
Ib145



A1a11
Ib145



A1a12
Ib145



A1a13
Ib145



A1a14
Ib145



A1a1
Ib161



A1a2
Ib161



A1a3
Ib161



A1a4
Ib161



A1a5
Ib161



A1a6
Ib161



A1a7
Ib161



A1a8
Ib161



A1a9
Ib161



A1a10
Ib161



A1a11
Ib161



A1a12
Ib161



A1a13
Ib161



A1a14
Ib161



A1a1
Ib177



A1a2
Ib177



A1a3
Ib177



A1a4
Ib177



A1a5
Ib177



A1a6
Ib177



A1a7
Ib177



A1a8
Ib177



A1a9
Ib177



A1a10
Ib177



A1a11
Ib177



A1a12
Ib177



A1a13
Ib177



A1a14
Ib177



A1a1
Ib193



A1a2
Ib193



A1a3
Ib193



A1a4
Ib193



A1a5
Ib193



A1a6
Ib193



A1a7
Ib193



A1a8
Ib193



A1a9
Ib193



A1a10
Ib193



A1a11
Ib193



A1a12
Ib193



A1a13
Ib193



A1a14
Ib193



A1a1
Ib209



A1a2
Ib209



A1a3
Ib209



A1a4
Ib209



A1a5
Ib209



A1a6
Ib209



A1a7
Ib209



A1a8
Ib209



A1a9
Ib209



A1a10
Ib209



A1a11
Ib209



A1a12
Ib209



A1a13
Ib209



A1a14
Ib209



A1a1
Ib225



A1a2
Ib225



A1a3
Ib225



A1a4
Ib225



A1a5
Ib225



A1a6
Ib225



A1a7
Ib225



A1a8
Ib225



A1a9
Ib225



A1a10
Ib225



A1a11
Ib225



A1a12
Ib225



A1a13
Ib225



A1a14
Ib225



A1a1
Ib241



A1a2
Ib241



A1a3
Ib241



A1a4
Ib241



A1a5
Ib241



A1a6
Ib241



A1a7
Ib241



A1a8
Ib241



A1a9
Ib241



A1a10
Ib241



A1a11
Ib241



A1a12
Ib241



A1a13
Ib241



A1a14
Ib241



A1a1
Ib257



A1a2
Ib257



A1a3
Ib257



A1a4
Ib257



A1a5
Ib257



A1a6
Ib257



A1a7
Ib257



A1a8
Ib257



A1a9
Ib257



A1a10
Ib257



A1a11
Ib257



A1a12
Ib257



A1a13
Ib257



A1a14
Ib257



A1a1
Ib273



A1a2
Ib273



A1a3
Ib273



A1a4
Ib273



A1a5
Ib273



A1a6
Ib273



A1a7
Ib273



A1a8
Ib273



A1a9
Ib273



A1a10
Ib273



A1a11
Ib273



A1a12
Ib273



A1a13
Ib273



A1a14
Ib273



A1a1
Ib289



A1a2
Ib289



A1a3
Ib289



A1a4
Ib289



A1a5
Ib289



A1a6
Ib289



A1a7
Ib289



A1a8
Ib289



A1a9
Ib289



A1a10
Ib289



A1a11
Ib289



A1a12
Ib289



A1a13
Ib289



A1a14
Ib289



A1a1
Ib305



A1a2
Ib305



A1a3
Ib305



A1a4
Ib305



A1a5
Ib305



A1a6
Ib305



A1a7
Ib305



A1a8
Ib305



A1a9
Ib305



A1a10
Ib305



A1a11
Ib305



A1a12
Ib305



A1a13
Ib305



A1a14
Ib305



A1a1
Ib321



A1a2
Ib321



A1a3
Ib321



A1a4
Ib321



A1a5
Ib321



A1a6
Ib321



A1a7
Ib321



A1a8
Ib321



A1a9
Ib321



A1a10
Ib321



A1a11
Ib321



A1a12
Ib321



A1a13
Ib321



A1a14
Ib321



A1a1
Ib337



A1a2
Ib337



A1a3
Ib337



A1a4
Ib337



A1a5
Ib337



A1a6
Ib337



A1a7
Ib337



A1a8
Ib337



A1a9
Ib337



A1a10
Ib337



A1a11
Ib337



A1a12
Ib337



A1a13
Ib337



A1a14
Ib337



A1a1
Ib353



A1a2
Ib353



A1a3
Ib353



A1a4
Ib353



A1a5
Ib353



A1a6
Ib353



A1a7
Ib353



A1a8
Ib353



A1a9
Ib353



A1a10
Ib353



A1a11
Ib353



A1a12
Ib353



A1a13
Ib353



A1a14
Ib353



A1a1
Ib369



A1a2
Ib369



A1a3
Ib369



A1a4
Ib369



A1a5
Ib369



A1a6
Ib369



A1a7
Ib369



A1a8
Ib369



A1a9
Ib369



A1a10
Ib369



A1a11
Ib369



A1a12
Ib369



A1a13
Ib369



A1a14
Ib369



A1a1
Ib385



A1a2
Ib385



A1a3
Ib385



A1a4
Ib385



A1a5
Ib385



A1a6
Ib385



A1a7
Ib385



A1a8
Ib385



A1a9
Ib385



A1a10
Ib385



A1a11
Ib385



A1a12
Ib385



A1a13
Ib385



A1a14
Ib385



A1a1
Ib401



A1a2
Ib401



A1a3
Ib401



A1a4
Ib401



A1a5
Ib401



A1a6
Ib401



A1a7
Ib401



A1a8
Ib401



A1a9
Ib401



A1a10
Ib401



A1a11
Ib401



A1a12
Ib401



A1a13
Ib401



A1a14
Ib401



A1a1
Ib417



A1a2
Ib417



A1a3
Ib417



A1a4
Ib417



A1a5
Ib417



A1a6
Ib417



A1a7
Ib417



A1a8
Ib417



A1a9
Ib417



A1a10
Ib417



A1a11
Ib417



A1a12
Ib417



A1a13
Ib417



A1a14
Ib417



A1a1
Ib433



A1a2
Ib433



A1a3
Ib433



A1a4
Ib433



A1a5
Ib433



A1a6
Ib433



A1a7
Ib433



A1a8
Ib433



A1a9
Ib433



A1a10
Ib433



A1a11
Ib433



A1a12
Ib433



A1a13
Ib433



A1a14
Ib433



A1a1
Ib449



A1a2
Ib449



A1a3
Ib449



A1a4
Ib449



A1a5
Ib449



A1a6
Ib449



A1a7
Ib449



A1a8
Ib449



A1a9
Ib449



A1a10
Ib449



A1a11
Ib449



A1a12
Ib449



A1a13
Ib449



A1a14
Ib449



A1a1
Ib465



A1a2
Ib465



A1a3
Ib465



A1a4
Ib465



A1a5
Ib465



A1a6
Ib465



A1a7
Ib465



A1a8
Ib465



A1a9
Ib465



A1a10
Ib465



A1a11
Ib465



A1a12
Ib465



A1a13
Ib465



A1a14
Ib465



A1a1
Ib481



A1a2
Ib481



A1a3
Ib481



A1a4
Ib481



A1a5
Ib481



A1a6
Ib481



A1a7
Ib481



A1a8
Ib481



A1a9
Ib481



A1a10
Ib481



A1a11
Ib481



A1a12
Ib481



A1a13
Ib481



A1a14
Ib481



A1a1
Ib497



A1a2
Ib497



A1a3
Ib497



A1a4
Ib497



A1a5
Ib497



A1a6
Ib497



A1a7
Ib497



A1a8
Ib497



A1a9
Ib497



A1a10
Ib497



A1a11
Ib497



A1a12
Ib497



A1a13
Ib497



A1a14
Ib497



A1a1
Ib513



A1a2
Ib513



A1a3
Ib513



A1a4
Ib513



A1a5
Ib513



A1a6
Ib513



A1a7
Ib513



A1a8
Ib513



A1a9
Ib513



A1a10
Ib513



A1a11
Ib513



A1a12
Ib513



A1a13
Ib513



A1a14
Ib513



A1a1
Ib529



A1a2
Ib529



A1a3
Ib529



A1a4
Ib529



A1a5
Ib529



A1a6
Ib529



A1a7
Ib529



A1a8
Ib529



A1a9
Ib529



A1a10
Ib529



A1a11
Ib529



A1a12
Ib529



A1a13
Ib529



A1a14
Ib529



A1a1
Ib545



A1a2
Ib545



A1a3
Ib545



A1a4
Ib545



A1a5
Ib545



A1a6
Ib545



A1a7
Ib545



A1a8
Ib545



A1a9
Ib545



A1a10
Ib545



A1a11
Ib545



A1a12
Ib545



A1a13
Ib545



A1a14
Ib545



A1a1
Ib561



A1a2
Ib561



A1a3
Ib561



A1a4
Ib561



A1a5
Ib561



A1a6
Ib561



A1a7
Ib561



A1a8
Ib561



A1a9
Ib561



A1a10
Ib561



A1a11
Ib561



A1a12
Ib561



A1a13
Ib561



A1a14
Ib561



A1a1
Ib577



A1a2
Ib577



A1a3
Ib577



A1a4
Ib577



A1a5
Ib577



A1a6
Ib577



A1a7
Ib577



A1a8
Ib577



A1a9
Ib577



A1a10
Ib577



A1a11
Ib577



A1a12
Ib577



A1a13
Ib577



A1a14
Ib577



A1a1
Ib593



A1a2
Ib593



A1a3
Ib593



A1a4
Ib593



A1a5
Ib593



A1a6
Ib593



A1a7
Ib593



A1a8
Ib593



A1a9
Ib593



A1a10
Ib593



A1a11
Ib593



A1a12
Ib593



A1a13
Ib593



A1a14
Ib593



A1a1
Ib609



A1a2
Ib609



A1a3
Ib609



A1a4
Ib609



A1a5
Ib609



A1a6
Ib609



A1a7
Ib609



A1a8
Ib609



A1a9
Ib609



A1a10
Ib609



A1a11
Ib609



A1a12
Ib609



A1a13
Ib609



A1a14
Ib609



A1a1
Ib625



A1a2
Ib625



A1a3
Ib625



A1a4
Ib625



A1a5
Ib625



A1a6
Ib625



A1a7
Ib625



A1a8
Ib625



A1a9
Ib625



A1a10
Ib625



A1a11
Ib625



A1a12
Ib625



A1a13
Ib625



A1a14
Ib625



A1a1
Ib641



A1a2
Ib641



A1a3
Ib641



A1a4
Ib641



A1a5
Ib641



A1a6
Ib641



A1a7
Ib641



A1a8
Ib641



A1a9
Ib641



A1a10
Ib641



A1a11
Ib641



A1a12
Ib641



A1a13
Ib641



A1a14
Ib641



A1a1
Ib657



A1a2
Ib657



A1a3
Ib657



A1a4
Ib657



A1a5
Ib657



A1a6
Ib657



A1a7
Ib657



A1a8
Ib657



A1a9
Ib657



A1a10
Ib657



A1a11
Ib657



A1a12
Ib657



A1a13
Ib657



A1a14
Ib657



A1a1
Ib673



A1a2
Ib673



A1a3
Ib673



A1a4
Ib673



A1a5
Ib673



A1a6
Ib673



A1a7
Ib673



A1a8
Ib673



A1a9
Ib673



A1a10
Ib673



A1a11
Ib673



A1a12
Ib673



A1a13
Ib673



A1a14
Ib673



A1a1
Ib689



A1a2
Ib689



A1a3
Ib689



A1a4
Ib689



A1a5
Ib689



A1a6
Ib689



A1a7
Ib689



A1a8
Ib689



A1a9
Ib689



A1a10
Ib689



A1a11
Ib689



A1a12
Ib689



A1a13
Ib689



A1a14
Ib689



A1a1
Ib705



A1a2
Ib705



A1a3
Ib705



A1a4
Ib705



A1a5
Ib705



A1a6
Ib705



A1a7
Ib705



A1a8
Ib705



A1a9
Ib705



A1a10
Ib705



A1a11
Ib705



A1a12
Ib705



A1a13
Ib705



A1a14
Ib705



A1a1
Ib721



A1a2
Ib721



A1a3
Ib721



A1a4
Ib721



A1a5
Ib721



A1a6
Ib721



A1a7
Ib721



A1a8
Ib721



A1a9
Ib721



A1a10
Ib721



A1a11
Ib721



A1a12
Ib721



A1a13
Ib721



A1a14
Ib721



A1a1
Ib737



A1a2
Ib737



A1a3
Ib737



A1a4
Ib737



A1a5
Ib737



A1a6
Ib737



A1a7
Ib737



A1a8
Ib737



A1a9
Ib737



A1a10
Ib737



A1a11
Ib737



A1a12
Ib737



A1a13
Ib737



A1a14
Ib737



A1a1
Ib753



A1a2
Ib753



A1a3
Ib753



A1a4
Ib753



A1a5
Ib753



A1a6
Ib753



A1a7
Ib753



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Compounds of formula I can be prepared according to the following methods and variations described in schemes 1-5. The variables R1, R2, R3, R4, R5a, R5b, R5c, R5d, A1, A2, A3, A4, and p are defined as above for formula I.
Compounds of formula I can, for example, be prepared by reaction of amines (or salts thereof) and quinazolines of the formula 4 as described by, for example, Ananthan et al, Bioorg. Med. Chem. Lett. 2002, 12, 2225 and outlined in Scheme 1. Depending on the conditions, bases such as triethylamine or potassium carbonate may be necessary. The reaction can be run in a wide variety of solvents including Tetrahydrofuran (THF), dioxane, and isopropanol or the like. The corresponding quinazolines of the formula 4 containing a leaving group (LG) wherein LG is a fluorine, chlorine, bromine, iodine, thioethers, sulfonates or another suitable leaving group can be prepared from quinazolinones of the formula 3 for example by reaction with a halogenating agent such as phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, thionyl chloride, phosphorus tribromide, phosphorus triiodide as described, for example, by Hayakawa, Bioorg. Med. Chem. 2006, 14, 6847. Depending on the conditions solvents such as dioxane, ether, toluene, DMF or the like can be employed. Quinazolinones of the formula 3 can be prepared from anthranilamides of formula 1 and aldehydes of formula 2 in the presence of reagents such as iron chloride (or hydrates thereof), iodine, sodium bisulfite or 2,3-dichloro-4,5-dicyano-1,4-benzoquinone as described, for example, by Wang et al, Bull. Chem. Soc. Jpn. 2006, 79, 1426.




Quinazolinones of the formula 3 can also be prepared as outlined in Scheme 2 from arylhalides of the formula 7 and amidines of the formula 8 under copper catalysis as described, for example, by Liu, Angew. Chem. Int. Ed. 2009, 48, 348. Alternatively, quinazolinones of the formula 3 can be prepared from anilines 5 and nitriles 6 under acidic conditions (e.g. hydrochloric acid) as described, for example, by Bogolubsky et al, J. Comb. Chem. 2008, 10, 858 for from amides of the formula 9 under basic conditions (e.g. sodium hydroxide) as described, for example, by Roy et al, J. Org. Chem. 2006, 71, 382.




Aminoquinazolines of the formula (I) can be prepared as outlined in Scheme 3 by a coupling reaction between intermediates of the formula 13 and intermediates of the formula 14 in the presence of metal catalyst derived from, for example, palladium, platinum, iron, copper or nickel where LG or Y are, for example, a fluorine, chlorine, bromine, iodine, triflate, thioether, boronic acid, boronate ester, trifluoroborate, or ganoborane or organostannane or other suitable leaving group, A phosphine-, amine-, sulfoxide-derived ligand and base such as potassium carbonate or triethylemine may also be required for the reaction as described, for example, by Itoh et al, Adv. Syn. Cat. 2004, 346, 1859. Intermediate of the formula 13 can be prepared from dichloroquinazoline of the formula 12 where LG is an analogous leaving group as described above. In turn the corresponding quinazolines of the formula 12 can be prepared from quinazoline-2,4-diones of the formula 11 using a similar method to that used to prepare intermediates of the formula 4. Quinazoline-2,4-diones of the formula 11 can be prepared from anthranilic acids of the formula 10 using reagents such as urea, isocyanate, thioisocyanate as described, for example, by Smits et al, J. Med. Chem. 2008, 7855.




Anthranilamides of the formula 1 can be prepared following an analogous route as that described in Scheme 4 [T. Sandmeyer, Helv. Chinn. Acta 1919, 2, 234 or S. J. Garden et al, Tetrahedron Lett. 1997, 38(9), 1501] starting from isatoic anhydrides of the formula 18 in one step using a reagent such as ammonia or in two steps using an amine-based nucleophile such an benzylamine, hydroxylamine or azide followed by reduction with, for example, hydrogen or ammonium formate as described, for example by Klaubert et al, J. Med. Chem. 1981, 24, 742 and Singh et at J. Heterocyclic Chem. 1990, 27, 2101. Isatoic anhydrides of the formula 18 can be synthesized from indole-2,3-diones of the formula 17 by oxidation with e.g. meta-chloroperbenzoic acid [G. M. Coppola, J. Heterocyclic Chem. 1987, 24, 1249], hydrogen peroxide or chromic acid in a solvent such as dichloromethane, acetic acid or water. In turn indole-2,3-diones of the formula 17 can be prepared in a Friedel-Crafts-type reaction from isonitrosoacetanilides of the formula 16 using a protic or Lewis acid such as sulfuric acid or aluminium trichloride. Finally isonitrosoacetanilides of the formula 16 can be prepared from substituted anilines of the formula 15 using chloral and hydroxylamine as reagents.




Anthranilamides of the formula 1, bearing strongly electron withdrawing substituents on the phenyl ring, are accessible through corresponding indole-2,3-diones of the formula 17 which in turn can be prepared following a route as that described by P. Hewawasam et al, Tetrahedron Lett. 1994, 35, 7303 and which is outlined in Scheme 5. Indole-2,3-diones of the formula 17 can be prepared by treatment of oxoacetic acid esters of the formula 20 with acids such as hydrochloric acid, trifluoroacetic acid, and triflic acid in solvents such as THF, water or CH2Cl2 as described, for example, by Hamashima et al., J. Am. Chem. Soc. 2005, 127, 10154. In turn oxoacetic acid esters of the formula 20, Rx being for example ethyl, methyl, can be prepared by exposure of carbamates of the formula 19 to strong carbon bases such as n-, sec-, or t-BuLi followed by reaction of the resultant carbanion with oxoacetic acid diesters. Finally carbamates of the formula 19 can be prepared from anilines of the formula 15 by reaction with di-t-butyldicarbonate.




If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or by customary modifications of the synthesis routes described.
The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils, which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or digestion.
The present invention also provides a method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of formula I or a salt or N-oxide thereof or a composition as defined above.
Preferably, the method of the invention serves for protecting plant propagation material (such as seed) and the plant which grows therefrom from invertebrate pest attack or infestation and comprises treating the plant propagation material (such as seed) with a pesticidally effective amount of a compound of formula I or an agriculturally acceptable salt or N-oxide thereof as defined above or with a pesticidally effective amount of an agricultural composition as defined above and below. The method of the invention is not limited to the protection of the “substrate” (plant, plant propagation materials, soil material etc.) which has been treated according to the invention, but also has a preventive effect, thus, for example, according protection to a plant which grows from a treated plant propagation materials (such as seed), the plant itself not having been treated.
In the sense of the present invention, “invertebrate pests” are preferably selected from arthropods and nematodes, more preferably from harmful insects, arachnids and nematodes, and even more preferably from insects, acarids and nematodes. In the sense of the present invention, “invertebrate pests” are most preferably insects.
The invention further provides an agricultural composition for combating such invertebrate pests, which comprises such an amount of at least one compound of the general formula I or at least one agriculturally useful salt or N-oxide thereof and at least one inert liquid and/or solid agronomically acceptable carrier that has a pesticidal action and, if desired, at least one surfactant.
Such a composition may contain a single active compound of the formula I or a salt or N-oxide thereof or a mixture of several active compounds I or their salts according to the present invention. The composition according to the present invention may comprise an individual isomer or mixtures of isomers as well as individual tautomers or mixtures of tautomers.
The compounds of the formula I and the pestidicidal compositions comprising them are effective agents for controlling arthropod pests and nematodes. Invertebrate pests controlled by the compounds of formula I include for example
insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Chematobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusiani and Zeiraphera canadensis; 
beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufi-manus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cero-toma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibi-alis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12 punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hip-pocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhyn-chus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyl-lopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria; 
dipterans (Diptera), for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya homi-nivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destruc-tor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hyso-cyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa; 
thrips (Thysanoptera), e.g. Dichromothrips corbetti, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci; 
hymenopterans (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, So-lenopsis geminata and Solenopsis invicta; 
heteropterans (Heteroptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor; 
homopterans (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Bemisia tabaci, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus persicae, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla pini, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Sogatella furcifera Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii; 
termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes flavipes, Reticulitermes lucifugus and Termes natalensis; 
orthopterans (Orthoptera), e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melano-plus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca ameri-cana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus; 
arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis; 
siphonatera, e.g. Xenopsylla cheopsis, Ceratophyllus spp.
The compositions and compounds of formula I are useful for the control of nematodes, especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species;
cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Het-erodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nema-todes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Paratylen-chus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.
In a preferred embodiment of the invention the compounds of formula I are used for controlling insects or arachnids, in particular insects of the orders Lepidoptera, Coleoptera, Thysanoptera and Homoptera and arachnids of the order Acarina. The compounds of the formula I according to the present invention are particularly useful for controlling insects of the order Thysanoptera and Homoptera.
The compounds of formula I or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by invertebrate pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of formula I. The term “crop” refers both to growing and harvested crops.
The compounds of formula I can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound according to the invention.
The formulations are prepared in a known manner (see e.g. for review U.S. Pat. No. 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, “Agglomeration”, Chemical Engi-neering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and of seq. WO 91/13546, U.S. Pat. Nos. 4,172,714, 4,144,050, 3,920,442, 5,180,587, 5,232,701, 5,208,030, GB 2,095,558, U.S. Pat. No. 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubermann, A., Formulation tech-nology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001, 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example by extending the active compound with auxiliaries suitable for the formulation of agrochemicals, such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, anti-foaming agents, anti-freezing agents, for seed treatment formulation also optionally colorants and/or binders and/or gelling agents.
Examples of suitable solvents are water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone [NMP], N-octylpyrrolidone [NOP]), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.
Suitable emulsifiers are non-ionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates).
Examples of dispersants are lignin-sulfite waste liquors and methylcellulose.
Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalene-sulfonic acid, alkylarylsulfonates, alkyl sulphates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulphated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene, oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropyl-ene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.
Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, etha-nol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.
Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides such as can be added to the formulation.
Suitable antiforming agents are for example antiforming agents based on silicon or magnesium stearate.
A suitable preservative is e.g. dichlorophen.
Seed treatment formulations may additionally comprise binders and optionally color-ants.
Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are block copolymers EO/PO surfactants but also polyvinylalcoholsl, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybute-nes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, poly-ethyleneimines (Lupasol®, Polymin®), polyethers, polyurethans, polyvinylacetate, ty-lose and copolymers derived from these polymers.
Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
An example of a gelling agent is carrageen (Satiagel®).
Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound(s). In this case, the active compound(s) are employed in a purity of from 90% to 100 by weight, preferably 95% to 100% % by weight (according to NMR spectrum).
For seed treatment purposes, respective formulations can be diluted 2- to 10-fold leading to concentrations in the ready to use preparations of 0.01 to 60% by weight active compound by weight, preferably 0.1 to 40% by weight.
The compounds of formula I can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compound(s) according to the invention.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wetable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active substance, wetting agent, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to %10, preferably from 0.01 to 1% per weight.
The active compound(s) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.
The following are examples of formulations:
1. Products for dilution with water for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.
A) Water-soluble concentrates (SL, LS)
10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of water or a water-soluble solvent, As an alternative, wetting agents or other auxiliaries are added. The active compound(s) dissolves upon dilution with water, whereby a formula-tion with 10% (w/w) of active compound(s) is obtained.
B) Dispersible concentrates (DC)
20 parts by weight of the active compound(s) are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvi-nylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of active compound(s) is obtained.
C) Emulsifiable concentrates (EC)
15 parts by weight of the active compound(s) are dissolved in 7 parts by weight of xy-lene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of active compound(s) is obtained.
D) Emulsions (EW, EO, ES)
25 parts by weight of the active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of wa-ter by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of active compound(s) is obtained.
E) Suspensions (SC, OD, FS)
In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, wetting agents and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.
F) Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of the active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetting agents and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 50% (w/w) of active compound(s) is obtained.
G) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)
75 parts by weight of the active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 75% (w/w) of active compound(s) is obtained.
H) Gel-Formulation (GF)
In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetting agents and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.
2. Products to be applied undiluted for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.
I) Dustable powders (DP, DS)
5 parts by weight of the active compound(s) are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5% (w/w) of active compound(s)
J) Granules (GR, FG, GG, MG)
0.5 parts by weight of the active compound(s) is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of active corn-pound(s) is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.
K) ULV solutions (UL)
10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of active compound(s), which is applied undiluted for foliar use.
The compounds of formula I are also suitable for the treatment of plant propagation materials (such as seed). Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible'powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pre-germinated the latter
In a preferred embodiment a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1 to 800 g/l of active ingredient, 1 to 200 g/l surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
Other preferred FS formulations of compounds of formula I for seed treatment comprise from 0.5 to 80 wt of the active ingredient, from 0.05 to 5 wt of a wetting agent, from 0.5 to 15 wt of a dispersing agent, from 0.1 to 5 wt of a thickener, from 5 to 20 wt of an anti-freeze agent, from 0.1 to 2 wt of an anti-foam agent, from 1 to 20 wt of a pigment and/or a dye, from 0 to 15 wt of a sticker/adhesion agent, from 0 to 75 wt of a filler/vehicle, and from 0.01 to 1 wt of a preservative.
Various types of oils, wetting agents, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents usually are admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.
The compounds of formula I are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).
For use against ants, termites, wasps, flies, mosquitoes, crickets, or cockroaches, com-pounds of formula I are preferably used in a bait composition.
The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spraying devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickiness, moisture retention or aging characteristics.
The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitoes, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.
Formulations of compounds of formula I as aerosols (e.g. in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably corn-posed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocar-bons (e.g. kerosenes) having boiling ranges of approximately 50 to 250° C., dimethyl-formamide, N-methylpyrrolidone, dimethyl sulphoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3 to 7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, am-photeric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.
The oil spray formulations differ from the aerosol recipes in that no propellants are used.
The compounds of formula I and their respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of formula I and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, non-wovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents for example are N,N-diethyl-meta-toluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl)acetic acid lactone, 2-ethyl-1,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and diethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.
The impregnation of curtains and bednets is done in general by dipping the textile ma-terial into emulsions or dispersions of the active compounds of formula I or spraying them onto the nets.
Methods which can be employed for treating the seed are, in principle, all suitable seed treatment and especially seed dressing techniques known in the art, such as seed coating (e.g. seed pelleting), seed dusting and seed imbibition (e.g. seed soaking). Here, “seed treatment” refers to all methods that bring seeds and the compounds of formula I into contact with each other, and “seed dressing” to methods of seed treatment which provide the seeds with an amount of the compounds of formula I, i.e. which generate a seed comprising the compound of formula I. In principle, the treatment can be applied to the seed at any time from the harvest of the seed to the sowing of the seed. The seed can be treated immediately before, or during, the planting of the seed, for example using the “planter's box” method. However, the treatment may also be carried out several weeks or months, for example up to 12 months, before planting the seed, for example in the form of a seed dressing treatment, without a substantially reduced efficacy being observed.
Expediently, the treatment is applied to unsown seed. As used herein, the term “unsown seed” is meant to include seed at any period from the harvest of the seed to the sowing of the seed in the ground for the purpose of germination and growth of the plant.
Specifically, a procedure is followed in the treatment in which the seed is mixed, in a suitable device, for example a mixing device for solid or solid/liquid mixing partners, with the desired amount of seed treatment formulations, either as such or after previ-ous dilution with water, until the composition is distributed uniformly on the seed. If ap-propriate, this is followed by a drying step.
The compounds of formula I, or the enantiomers, diastereomers or veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals.
An object of the present invention is therefore also to provide new methods to control parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in lower doses than existing pesticides. And another object of the invention is to provide pesticides for animals, which provide a long residual control of the parasites.
The invention also relates to compositions containing a parasiticidally effective amount of compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and an acceptable carrier, for combating parasites in and on animals.
The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of formula I or the enantiomers or veterinarily acceptable salts thereof or a composition comprising it.
The present invention also provides a non-therapeutic method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of formula I or the enantiomers or veterinarily acceptable salts thereof or a composition comprising it. The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises including a parasiticidally effective amount of a compound of formula I or the enantiomers or veterinarily acceptable salts thereof in a composition comprising it.
The invention relates further to the use of compounds of formula I for treating, controlling, preventing or protecting animals against infestation or infection by parasites.
The invention relates also to the use of a compound of formula I, or a composition comprising it, for the manufacture of a medicament for the therapeutic treatment of animals against infections or infestions by parasites.
Activity of compounds against agricultural pests does not suggest their suitability for control of endo- and ectoparasites in and on animals which requires, for example, low, non-emetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.
Surprisingly it has now been found that compounds of formula I are suitable for combating endo- and ectoparasites in and on animals. The compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.
Compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.
Compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.
Infestations in warm-blooded animals and fish include, but are not limited to lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.
The compounds of formula I are especially useful for combating ectoparasites.
The compounds of formula I are especially useful for combating endoparasites.
The compounds of formula I are especially useful for combating parasites of the following orders and species, respectively:
fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, 
cockroaches (Blattaria-Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis, 
flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinque fasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, 
lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus. 
ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersonii Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae, 
Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp,
Bugs (Heteropterida); Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus, 
Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp,
Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp,
Roundworms Nematoda:
Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp,
Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,
Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale, 
Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi, 
Camallanida, e.g. Dracunculus medinensis (guinea worm)
Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.,
Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp,
Planarians (Plathelminthes):
Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp,
Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.
Applications
The present invention relates to the therapeutic and the non-therapeutic use of compounds of formula I for controlling and/or combating parasites in and/or on animals.
The compounds of formula I may be used to protect the animals from attack or infestation by parasites by contacting them with a parasitically effective amount of compounds of formula I. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at it's locus for the latter) and indirect contact (applying the compounds/compositions to the locus of the parasite). The contact of the parasite through application to its locus is an example of a non-therapeutic use of compounds of formula I.
“Locus” as defined above means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal. The compounds of the invention can also be applied preventively to places at which occurrence of the pests or parasites is expected.
The compounds of formula I can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits).
The administration can be carried out prophylactically, therapeutically or non-therapeutically.
Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.
In general, “parasiticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
Generally it is favorable to apply the compounds of formula I in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.
Formulations
For oral administration to warm-blooded animals, the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the formula I compounds may be administered to the animals in their drinking, water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the formula I compounds may be formulated into an implant for subcutaneous administration. In addition the formula I compound may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.
The formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
Suitable preparations are:

    
    
        Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;
        Emulsions and suspensions for oral or dermal administration; semi-solid preparations;
        Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;
        Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.
    
    


Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.
Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methyl-pyrrolidone, 2-pyrrolidone, and mixtures thereof.
The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.
Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.
Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.
Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.
Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.
Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.
Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such, as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.
It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.
Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. The thickeners employed are the thickeners given above.
Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.
Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.
Suitable solvents which are: water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethyllacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n-butylpyrrolidone or noctylpyrrolidone, N-methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxymethylene-1,3-diox-olane and glycerol formal.
Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.
Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.
Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butyl hydroxyanisole, tocopherol.
Suitable light stabilizers are, for example, novantisolic acid.
Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.
Emulsions can be administered orally, dermally or as injections.
Emulsions are either of the water-in-oil type or of the oil-in-water type.
They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.
Suitable hydrophobic phases (oils) are
liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length C8-C12 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the C8-C10 fatty acids,
fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C16-C18, isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C12-C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof.
Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.
Suitable emulsifiers are:
non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;
ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin; anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt; cation-active surfactants, such as cetyltrimethylammonium chloride.
Suitable further auxiliaries are: substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.
Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.
Liquid suspending agents are all homogeneous solvents and solvent mixtures.
Suitable wetting agents (dispersants) are the emulsifiers given above.
Other auxiliaries which may be mentioned are those given above.
Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.
For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.
Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.
Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.
Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.
The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of formula I.
Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 percent by weight, preferably from 0.1 to 65 percent by weight, more preferably from 1 to 50 percent by weight, most preferably from 5 to 40 percent by weight.
Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 percent by weight, preferably of 1 to 50 percent by weight.
Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 percent by weight, preferably of 0.05 to 0.9 percent by weight, very particularly preferably of 0.005 to 0.25 percent by weight.
The compositions comprising the compounds of formula I can be applied orally, parenterally or topically, respectively dermally. For example, optionally the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.
Generally it is favorable to apply solid formulations which release compounds of formula I in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.
For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of formula I. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 03/086075.
The active compounds can be applied solely or in a mixture with synergists or with other active compounds which act against pathogenic endo- and ectoparasites. For example, the active compounds of formula I can be applied in mixtures with synthetic coccidiosis compounds, polyetherantibiotics as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin or with other pesticides which are described in the list M below.
Compositions to be used according to this invention for agricultural or veterinary purposes may also contain other active ingredients, for example other pesticides, insecticides, herbicides, fungicides, bactericides, fertilizers such as ammonium nitrate, urea, potash, and super-phosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.
These agents can be admixed with the agents used according to the invention in a weight ratio of 1:10 to 10:1. Mixing the compounds of formula I or the compositions comprising them in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.
The following list M of pesticides together with which the compounds according to the invention can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation:

    M.1. Organo(thio)phosphate compounds: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, flupyrazophos, fosthiazate, heptenophos, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;
    M.2. Carbamate compounds: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate;
    M.3. Pyrethroid compounds: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gammacyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, thetacypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, taufluvalinate, halfenprox, imiprothrin, metofluthrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tralomethrin, transfluthrin;
    M.4. Juvenile hormone mimics: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen;
    M.5. Nicotinic receptor agonists/antagonists compounds: acetamiprid, bensultap, cartap hydrochloride, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, nicotine, spinosad (allosteric agonist), spinetoram (allosteric agonist), thiacloprid, thiocyclam, thiosultap-sodium and AKD1022.
    M.6. GABA gated chloride channel antagonist compounds: chlordane, endosulfan, gamma-HCH (lindane); ethiprole, fipronil, pyrafluprole, pyriprole
    M.7. Chloride channel activators: abamectin, emamectin benzoate, milbemectin, lepimectin;
    M.8. METI I compounds: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, rotenone;
    M.9. METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;
    M.10. Uncouplers of oxidative phosphorylation: chlorfenapyr, DNOC;
    M.11. Inhibitors of oxidative phosphorylation: azocyclotin, cyhexatin, diafenthiuron, fenbutatin oxide, propargite, tetradifon;
    M.12. Moulting disruptors: cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide;
    M.13. Synergists: piperonyl butoxide, tribufos;
    M.14. Sodium channel blocker compounds: indoxacarb, metaflumizone;
    M.15. Fumigants: methyl bromide, chloropicrin sulfuryl fluoride;
    M.16. Selective feeding blockers: crylotie, pymetrozine, flonicamid;
    M.17. Mite growth inhibitors: clofentezine, hexythiazox, etoxazole;
    M.18. Chitin synthesis inhibitors: buprofezin, bistrifluoron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;
    M.19. Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
    M.20. Octapaminergic agonists: amitraz;
    M.21. Ryanodine receptor modulators: flubendiamide, (R)-,(S)-3-Chlor-N-1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid (M21.1)
    M.22. Isoxazoline compounds: 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-pyridin-2-ylmethyl-benzamide (M22.1), 445-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoro-ethyl)-benzamide (M22.2), 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide (M22.3), 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-amide (M22.4) and 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-[(methoxyimino)methyl]-2-methylbenzamide (M22.5);
    M.23. Anthranilamide compounds: chloranthraniliprole, cyantraniliprole, 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [4-cyano-2-(1-cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide (M23.1), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2-chloro-4-cyano-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M23.2), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2-bromo-4-cyano-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide(M23.3), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2-bromo-4-chloro-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide(M23.4), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2,4-dichloro-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M23.5), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [4-chloro-2-(1-cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide (M23.6), N′-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-hydrazinecarboxylic acid methyl ester (M23.7), N′-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-N′-methyl-hydrazinecarboxylic acid methyl ester (M23.8),
    N′-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-N,N′-dimethyl-hydrazinecarboxylic acid methyl ester (M23.9), N′-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-hydrazinecarboxylic acid methyl ester (M23.10), N′-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-n-methyl-hydrazinecarboxylic acid methyl ester (M23.11) and N′-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-N,N′-dimethyl-hydrazinecarboxylic acid methyl ester (M23.12);
    M.24. Malononitrile compounds: 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoro-propyl)malononitrile (CF2H—CF2—CF2—CF2—CH2—C(CN)2—CH2—CH2—CF3) (M24.1) and 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4-pentafluorobutyl)-malonodinitrile (CF2H—CF2—CF2—CF2—CH2—C(CN)2—CH2—CH2—CF2—CF3) (M24.2);
    M.25. Microbial disruptors: Bacillus thuringiensis subsp. Israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Tenebrionis; 
    M.26. Aminofuranone compounds:
    4-{[(6-Bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.1),
    4-{[(6-Fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-on (M26.2),
    4-{[(2-Chloro1,3-thiazolo-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.3),
    4-{[(6-Chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.4),
    4-{[(6-Chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-on (M26.5),
    4-{[(6-Chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (M26.6),
    4-{[(5,6-Dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.7),
    4-{[(6-Chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (M26.8),
    4-{[(6-Chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (M26.9) and
    4-{[(6-Chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (M26.10);
    M.27. Various compounds: aluminium phosphide, amidoflumet, benclothiaz, benzoximate, bifenazate, borax, bromopropylate, cyanide, cyenopyrafen, cyflumetofen, chinomethionate, dicofol, fluoroacetate, phosphine, pyridalyl, pyrifluquinazon, sulfur, organic sulfur compounds, tartar emetic, sulfoxaflor, N—R′-2,2-dihalo-1-R′′cyclo-propanecarboxamide-2-(2,6-dichloro-α,α,α-trifluoro-ptolyl)hydrazone or N—R′-2,2-di(R′′′)propionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-hydrazone, wherein R′ is methyl or ethyl, halo is chloro or bromo, R′′ is hydrogen or methyl and R′′′ is methyl or ethyl, 4-But-2-ynyloxy-6-(3,5-dimethyl-piperidin-1-yl)-2-fluoro-pyrimidine (M27.1), Cyclopropaneacetic acid, 1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-[2-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl]ester(M27.2) and 8-(2-Cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane(M27.3).


The commercially available compounds of the group M may be found in The Pesticide Manual, 14th Edition, British Crop Protection Council (2006).
Paraoxon and their preparation have been described in Farm Chemicals Handbook, Volume 88, Meister Publishing Company, 2001. Flupyrazofos has been described in Pesticide Science 54, 1988, p. 237-243 and in U.S. Pat. No. 4,822,779. AKD 1022 and its preparation have been described in U.S. Pat. No. 6,300,348. The anthranilamides M23.1 to M23.6 have been described in WO 2008/72743 and WO 200872783, those M23.7 to M23.12 in WO2007/043677. The phthalamide M 21.1 is known from WO 2007/101540. The alkynylether compound M27.1 is described e.g. in JP 2006131529. Organic sulfur compounds have been described in WO 2007060839. The isoxazoline compounds M 22.1 to M 22.5 have been described in e.g. WO2005/085216, WO 2007/079162 and WO 2007/026965. The aminofuranone compounds M 26.1 to M 26.10 have been described eg. in WO 2007/115644. The pyripyropene derivative M 27.2 has been described in WO 2008/66153 and WO 2008/108491. The pyridazin compound M 27.3 has been described in JP 2008/115155. Malononitrile compounds as those (M24.1) and (M24.2) have been described in WO 02/089579, WO 02/090320, WO 02/090321, WO 04/006677, WO 05/068423, WO 05/068432 and WO 05/063694.
The following list of active substances, in conjunction with which the compounds according to the invention can be used, is intended to illustrate the possible combinations but does not limit them. Fungicidal mixing partners are in particular those selected from the following groups:

    F.I) Respiration Inhibitors
    F.I-1) Inhibitors of complex III at Qo site (e.g. strobilurins)
    strobilurins: azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoximmethyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, methyl (2-chloro-5[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate and 2 (2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N methyl-acetamide; oxazolidinediones and imidazolinones: famoxadone, fenamidone;
    F.I-2) Inhibitors of complex II (e.g. carboxamides):
    carboxanilides: benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr, isopyrazam, isotianil, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4 methyl-thiazole-5-carboxanilide, N-(3′,4′,5′ trifluorobiphenyl-2 yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4 carboxamide, N-(4′-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1-methyl-1H pyrazole-4-carboxamide and N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5 fluoro-1H-pyrazole-4 carboxamide;
    F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom;
    F.I-4) Other respiration inhibitors (complex I, uncouplers) diflumetorim; tecnazen; ferimzone; ametoctradin; silthiofam;
    nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam, nitrthal-isopropyl, organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;
    F.II) Sterol biosynthesis inhibitors (SBI fungicides)
    F.II-1) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles, imidazoles) triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole;
    imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz, triflumizole; pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforine;
    F.II-2) Delta14-reductase inhibitors (Amines, e.g. morpholines, piperidines) morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph;
    piperidines: fenpropidin, piperalin;
    spiroketalamines: spiroxamine;
    F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;
    F.III) Nucleic acid synthesis inhibitors
    F.III-1) RNA, DNA synthesis
    phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;
    isoxazoles and iosothiazolones: hymexazole, octhilinone;
    F.III-2) DNA topisomerase inhibitors: oxolinic acid;
    F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase)
    hydroxy (2-amino)-pyrimidines: bupirimate;
    F.IV) Inhibitors of cell division and or cytoskeleton
    F.IV-1) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl;
    triazolopyrimidines: 5-chloro-7 (4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5 a]pyrimidine
    F.IV-2) Other cell division inhibitors
    benzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide;
    F.IV-3) Actin inhibitors: benzophenones: metrafenone;
    F.V) Inhibitors of amino acid and protein synthesis
    F.V-1) Methionine synthesis inhibitors (anilino-pyrimidines)
    anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin, pyrimethanil;
    F.V-2) Protein synthesis inhibitors (anilino-pyrimidines)
    antibiotics: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
    F.VI) Signal transduction inhibitors
    F.VI-1) MAP/Histidine kinase inhibitors (e.g. anilino-pyrimidines) dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;
    phenylpyrroles: fenpiclonil, fludioxonil;
    F.VI-2) G protein inhibitors: quinolines: quinoxyfen;
    F.VII) Lipid and membrane synthesis inhibitors
    F.VII-1) Phospholipid biosynthesis inhibitors organophosphorus compounds: edifenphos, iprobenfos, pyrazophos;
    dithiolanes: isoprothiolane;
    F.VII-2) Lipid peroxidation
    aromatic hydrocarbons: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
    F.VII-3) Carboxyl acid amides (CAA fungicides)
    cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid, pyrimorph;
    valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb, valifenalate and N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl)carbamic acid-(4-fluorophenyl)ester;
    F.VII-4) Compounds affecting cell membrane permeability and fatty acides carbamates: propamocarb, propamocarb-hydrochlorid
    F.VIII) Inhibitors with Multi Site Action
    F.VIII-1) Inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
    F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasulphocarb, metiram, propineb, thiram, zineb, ziram;
    F.VIII-3) Organochlorine compounds (e.g. phthalimides, sulfamides, chloronitriles): anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pentachiorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
    F.VIII-4) Guanidines: guanidine, dodine, dodine free base, guazatine, guazatineacetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);
    F.VIII-5) Ahtraquinones: dithianon;
    F.IX) Cell wall synthesis inhibitors
    F.IX-1) Inhibitors of glucan synthesis: validamycin, polyoxin B;
    F.IX-2) Melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamide, dicyclomet, fenoxanil;
    F.X) Plant defence inducers
    F.X-1) Salicylic acid pathway: acibenzolar-5-methyl;
    F.X-2) Others: probenazole, isotianil, tiadinil, prohexadione-calcium;
    phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts;
    F.XI) Unknown mode of action:
    bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, flumetover, flusulfamide, flutianil, methasulfocarb, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchromen-4-one, N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N methyl formamidine, N′ (4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N′-(5-difluoromethyl-2 methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amide, 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide, methoxyacetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and N-Methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamide, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine, 3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole-1 carbothioic acid S-allyl ester, N-(6-methoxy-pyridin-3-yl)cyclopropane-carboxylic acid amide, 5-chloro-1 (4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole, 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;
    F.XI) Growth regulators:
    abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6 benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodobenzoic acid, trinexapac-ethyl and uniconazole;
    F.XII) Biological control agents
    antifungal biocontrol agents: Bacillus substilis strain with NRRL No. B-21661 (e.g. RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest, Inc., USA.), Bacillus pumilus strain with NRRL No. B-30087 (e.g. SONATA® and BALLAD® Plus from AgraQuest, Inc., USA), Ulocladium oudemansii (e.g. the product BOTRY-ZEN from BotriZen Ltd., New Zealand), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., New Zealand).


The invertebrate pest, i.e. arthropodes and nematodes, the plant, soil or water in which the plant is growing can be contacted with the compound(s) of formula I or the composition(s) containing them by any application method known in the art. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the invertebrate pest or plant—typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the invertebrate pest or plant).
Moreover, invertebrate pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of formula I. As such the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.
“Locus” in general means a habitat, breeding ground, cultivated plants, plant propagation material (such as seed), soil, area, material or environment in which a pest or parasite is growing or may grow.
In general “pesticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
The compounds of formula I and the compositions comprising said compounds can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of formula I are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywood, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.
The compounds of formula I can also be applied preventively to places at which occurrence of the pests is expected.
The compounds of formula I may also be used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of formula I. As such, “contacting the plant” includes both direct contact (applying the compounds/compositions directly on the pest and/or plant—typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).
In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m2 treated material, desirably from 0.1 g to 50 g per m2.
Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95% by weight, preferably from 0.1 to 45% by weight, and more preferably from 1 to 25% by weight of at least one repellent and/or insecticide.
For use in bait compositions, the typical content of active ingredient is from 0.001% by weight to 15% by weight, desirably from 0.001% by weight to 5% by weight of active compound.
For use in spray compositions, the content of active ingredient is from 0.001 to 80% by weight, preferably from 0.01 to 50% by weight and most preferably from 0.01 to 15% by weight.
For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 5 g to 600 g per hectare, more desirably from 10 g to 300 g per hectare.
In the treatment of seed, the application rates of the active ingredients are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 1 kg per 100 kg of seed, in particular from 1 g to 250 g per 100 kg of seed, in particular from 50 g to 150 g per 100 kg of seed.
The present invention is now illustrated in further detail by the following examples which are not intended to limit the invention to them.


I. PREPARATION EXAMPLES
Products were characterized by HPLC (High Performance Liquid Chromatography Mass Spectrometry). HPLC was carried out using an analytic RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany) which was operated at 40° C. Acetonitrile with 0.1% by volume of a trifluoroacetic acid/water mixture and 0.1% by volume of trifluoroacetic acid served as mobile phase; flow rate: 1.8 mL/min and injection volume: 2 μl.
Example 1
[2-(4-Chloro-phenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine (I-99)




1.1 2-(4-Chlorophenyl)-7-trifluoromethyl-3H-quinazolin-4-one:
To a stirred suspension of 2-amino-4-(trifluoromethyl)benzamide (33.6 g, 0.16 mol) in water (750 mL) was added dropwise 4-chlorobenzaldehyde. Iron trichloride hexahydrate (133 g) was then added in portions. The reaction mixture was then heated at reflux for 24 h. After allowing the suspension to cool to room temperature, the precipitate was isolated by vacuum filtration washing with water (3×500 mL) and dried under vacuum (10 mbar, 50° C.). Yield=50 g, 94%; HPLC-mass spectrometry (LC-MS): 3.7 min, 325 (M+).
1.2 4-Chloro-2-(4-chloro-phenyl)-7-trifluoromethylquinazoline
To a stirred suspension of 2-(4-chlorophenyl)-7-trifluoromethyl-3H-quinazolin-4-one (50 g, 0.15 mol) in dioxane (400 mL) was added dropwise phosphorus oxychloride (43 mL, 0.46 mol). The suspension was then heated at reflux for 2 h then allowed to cool to room temperature and evaporated under reduced pressure. The remaining solid was dissolved in dioxane (1 L) and an aqueous solution of sodium hydroxide (50 mL, 10% weight/weight (w/w)) was added dropwise maintaining the internal temperature≦10° C.). Water (1 L) was then added to the resultant suspension followed by the dropwise addition of a further quantity of aqueous sodium hydroxide (90 mL, 10% w/w). The precipitate was isolated by vacuum filtration washing with water (3×500 mL) and dried under vacuum (10 mbar, 50° C.). Yield=49 g, 93%; LC-MS: 4.7 min, 343 (M+); 1H NMR (dimethylsulfoxide (DMSO)-d6) δ 7.68 (d, 2 H, J=8.9 Hz), 8.12 (dd, 1 H, J=8.9, 1.8 Hz), 8.48-8.54 (m, 4 H).
1.3 [2-(4-Chloro-phenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine
To a stirred solution of 4-chloro-2-(4-chloro-phenyl)-7-trifluoromethylquinazoline (52.0 g, 0.15 mol) in THF (400 mL) at 0° C. was added dropwise a solution of ethylamine (0.45 mol, 230 mL, 2 M in THF. The ice-bath was then removed and the reaction mixture was allowed to stir at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure then partitioned between ethyl acetate (400 mL) and water (400 mL) removing any undissolved solid by vacuum filtration. The filtrate was concentrated to approximately 200 mL and the resultant precipitate was removed by vacuum filtration. The filtrate was again concentrated to approximately 100 mL volume and the resultant precipitate was removed by vacuum filtration. Finally the filtrate was cooled to 0° C. upon which [2-(4-chloro-phenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine precipitated from solution. The precipitate (30 g) was isolated by vacuum filtration and dried under vacuum (10 mbar, 50° C.). A second amount of the precipitate of equal purity (19.6 g) was obtained following concentration of the filtrate to approximately 50 mL volume, cooling to 0° C., filtration and drying under vacuum. Combined yield=49.6 g, 93%; LC-MS: 2.9 min, 352 (M+); 1H NMR (DMSO-d6): δ 1.38 (t, 1 H, J=7 Hz), 3.77-3.85 (m, 2 H), 7.46 (d, 2 H, J=8.7 Hz), 7.64 (dd, 1 H, J=8.3, 1.8 Hz), 7.72-7.78 (br s, 1 H), 8.09 (s, 1 H), 8.17 (d, 1 H, J=8.3 Hz), 8.59 (d, 2 H, J=8.7 Hz).
Example 2
[2-(4-Trifluoromethylphenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine (I-209)




2.1 7-Trifluoromethyl-1H-quinazoline-2,4-dione
2-Amino-4-trifluoromethylbenzoic acid (25.0 g, 122 mmol) and urea (75.0 g, 1.2 mol) were combined and heated at 200° C. while stirring. After 1 h, the reaction mixture was allowed to cool to 100° C. and water (100 mL) was added. The reaction mixture was then allowed to cool to room temperature and the solid was isolated by vacuum filtration washing with water (500 mL). The solid was then dried under vacuum (10 mbar, 50° C.). Yield=24 g, 86%; LC-MS: 2.1 min, 230 (M+); 1H NMR (DMSO-d6) δ 7.44 (s, 1 H) 7.47 (d, 1 H), 8.07 (d, 1 H), 11.43 (br s, 1 H), 11.56 (br s, 1 H).
2.2 (2-Chloro-7-trifluoromethyl-quinazolin-4-yl)ethylamine
To a stirred suspension of 7-trifluoromethyl-1H-quinazoline-2,4-dione (25 g, 0.11 mol) and N,N-dimethylaniline (13.1 g, 0.11 mol) at 0° C. was added phosphorus oxychloride (101 mL, 1.1 mol) and the reaction mixture was heated at reflux for 6 h. The reaction mixture was allowed to cool to room temperature then concentrated under reduced pressure. The resultant solid was dissolved in THF (50 mL) then cooled to 0° C. and a solution of ethylamine (10 mL, 2 molar in THF) was added dropwise with stirring. After 2 h, the reaction mixture was concentrated under reduced pressure, diluted with water (250 mL) and extracted with ethyl acetate (2×150 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Yield=14 g, 47%; LC-MS: 3.1 min, 276 (M+); 1H NMR (DMSO-d6): δ 1.26 (apparent t, 3 H, J=7 Hz), 3.57 (ddd, 2H, J=12.7, 7.3, 5.6 Hz), 7.84 (dd, 1 H, J=8.7, 1.6 Hz), 7.93 (s, 1 H), 8.49 (d, 1 H, J=8.7 Hz), 9.05 (apparent t, 1 H, J=5 Hz).
2.3 [2-(4-Trifluoromethylphenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine
A solution of (2-chloro-7-trifluoromethyl-quinazolin-4-yl)ethylamine (276 mg, 1.00 mmol), p-trifluoromethylphenylboronic acid (285 mg, 1.50 mmol), tetrakis(triphenylphosphine)palladium (116 mg, 0.10 mmol) and sodium carbonate (0.21 g, 2.0 mmol) in dimethoxyethane/water (3 mL, 2:1) was heated at 80° C. for 16 h. The reaction mixture was then concentrated under reduced pressure, diluted with water (50 mL) and extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by flash chromatography using cyclohexane:ethyl acetate (4:1) as solvent afforded [2-(4-trifluoromethylphenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine. Yield=0.20 g, 52%; LC-MS: 3.2 min, 385 (M+); 1H NMR (DMSO-d6): δ 1.34 (t, 3 H, J=7.2 Hz), 3.68-3-78 (m, 2 H), 7.82 (dd, 1 H, J=8.6, 1.7 Hz), 7.88 (d, 2 H, J=8.1 Hz), 8.07 (s, 1 H), 8.50 (d, 1 H, J=8.6 Hz), 8.67 (d, 2 H, J=8.1 Hz), 8.70-8.76 (m, 1 H).
Example 3
[2-(4-Chlorophenyl)-5,6,difluoro-7-trifluoromethylquinazolin-4-yl]ethylamine (I-401)




3.1 2,3-Difluoro-6-iodo-4-trifluoromethylbenzoic acid
A suspension of 2,3-difluoro-4-trifluoromethylbenzoic acid (1.00 g, 4.42 mmol), palladium (II) acetate (0.199 g, 0.88 mmol) and N-iodosuccinimide (1.19 g, 5.31 mmol) in dimethylformamide (10 mL) were heated at 100° C. for 2 d. The reaction mixture was then concentrated under reduced pressure, diluted with ethyl acetate (100 mL) and washed with water (3×25 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to afford a brown solid (1.53) g which was used without further purification. LC-MS: 2.6 min, 353 (M+).
3.2 2-(4-Chlorophenyl)-5,6-difluoro-7-trifluoromethyl-3H-quinazolin-4-one
A suspension of crude 2,3-difluoro-6-iodo-4-trifluoromethylbenzoic acid (1.00 g), 4-chlorobenzamide hydrochloride (0.814 g, 4.26 mmol), copper (I) iodide (0.108 g), caesium carbonate (1.85 g, 5.68 mmol) in dimethylformamide (8 mL) were stirred under nitrogen at room temperature for 1 week. The reaction mixture was then diluted with ethyl acetate (100 mL) and washed with hydrochloric acid (1 M, 25 mL) and water (25 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure (0.98 g). The reaction was repeated with crude 2,3-difluoro-6-iodo-4-trifluoromethylbenzoic acid (0.50 g) to afford an additional portion (0.57 g) of the quinazolin-4-one. LC-MS: 3.6 min, 361 (M+).
3.3 4-chloro-2-(4-chlorophenyl)-5,6-difluoro-7-trifluoromethylquinazoline
To a suspension of the above quinazolin-4-one (1.50 g) in dioxane (45 mL) was added phosphorus oxychloride (3.9 mL, 41 mmol) and the resultant solution was heated at reflux for 16 h. The reaction mixture was then concentrated under reduced pressure to afford a gummy solid which was used without further purification.
3.4 [2-(4-Trifluoromethylphenyl)-5,6,difluoro-7-trifluoromethylquinazolin-4-yl]ethylamine
A suspension of the above crude quinazoline and ethylamine (2 M in THF, 25 mL) was stirred at room temperature for 16 h. The reaction mixture was then concentrated under reduced pressure, diluted with ethyl acetate (75 mL) and washed with water (25 mL), aqueous sodium carbonate (25 mL) and water (25 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to afford a crystalline solid. Recrystallization from hot cyclohexane:ethyl acetate (4:1) afforded [2-(4-chlorophenyl)-5,6,difluoro-7-trifluoromethylquinazolin-4-yl)ethylamine. Yield=0.10 g, 6% over 4 steps. LC-MS: 4.6 min, 388 (M+); 1H NMR (tetrahydrofuran (THF)-d6): δ 1.38 (apparent t, J=7 Hz, 3 H), 3.79-3.87 (m, 2 H), 7.47 (apparent d, J=8.8 Hz, 2 H), 7.51-7.59 (broad s, 1 H), 7.96 (dd, J=6.2, 1.4 Hz, 1 H), 8.54 (apparent d, J=8.8 Hz, 2 H).
Compounds of formula I prepared according to the above mentioned method together with their physico-chemical data are compiled below in Tables E, F and G. The corresponding physico-chemical data (LC/MS) wherein tR is retention time in minutes and M is the mass of respective molecular ion are listed in the Tables.
In Table E, compounds are of the general formula:




wherein RE is a mono- or dialkylamino derivative:

    
    
        RE is
    
    






and # denotes the binding site to the remainder










TABLE E





I
RE
LC/MS







I-1




tR:: 3.751′ M = 470.9


 


I-2




tR:: 3.672′ M = 437.9


 


I-3




tR:: 3.591′ M = 451.9


 


I-4




tR:: 3.742′ M = 437.9


 


I-5




tR:: 2.532′ M = 380.8


 


I-6




tR:: 3.057′ M = 439.9


 


I-7




tR:: 4.068′ M = 447.9


 


I-8
cyclopropylamino
tR:: 3.183′




M = 364.1


 


I-9




tR:: 3.678′ M = 461.6


 


I-10
cyclopentylamino
tR:: 3.421′




M = 391.8


I-11
#-CH2CH2OCH2CH3
tR:: 3.073′




M = 396.0


 


I-12




tR:: 3.464′ M = 440.0


 


I-13




tR:: 3.083′ M = 410.0


 


I-14




tR:: 2.507′ M = 409.1


 


I-15




tR:: 4.063′ M = 418.8


 


I-16




tR:: 3.355′ M = 389.8


 


I-17




tR:: 3.592′ M = 407.8


 


I-18




tR:: 3.91′ M = 404.8


 


I-19




tR:: 2.974′ M = 429.8


 


I-20




tR:: 4.559′ M = 393.8


 


I-21




tR:: 3.395′ M = 423.8


 


I-22




tR:: 4.275′ M = 459.9


 


I-23




tR:: 3.286′ M = 379.8


 


I-24




tR:: 3.812′ M = 465.9


 


I-25




tR:: 3.932′ M = 451.9


 


I-26




tR:: 3.174′ M = 423.8


 


I-27




tR:: 2.746′ M = 379.8


 


I-28
benzyl
tR:: 3.520′




M = 414.1


I-29
propyl
tR:: 3.330′




M = 366.1


I-30
cyclohexyl
tR:: 3.524′




M = 406.0


I-31
#-CH2C(CH3)3
tR:: 3.461′




M = 394.1


 


I-32




tR:: 3.541′ M = 439.0


 


I-33




tR:: 2.731′ M = 396.0


 


I-34




tR:: 3.908′ M = 436.1


 


I-35




tR:: 2.831′ M = 451.1


 


I-36




tR:: 2.560′ M = 409.0


 


I-37




tR:: 3.457′ M = 394.0


 


I-38
#-CH2CH2OCH3
tR:: 2.897′




M = 382.0


 


I-39




tR:: 3.201′ M = 495.1


 


I-40




tR:: 3.796′ M = 439.9


 


I-41




tR:: 3.499′ M = 441.9


 


I-42




tR:: 3.584′ M = 390.8


 


I-43




tR:: 3.415′ M = 451.9


 


I-44




tR:: 3.755′ M = 455.9


 


I-45




tR:: 2.881′ M = 436.9


 


I-46
#-CH2cyclopentyl
tR:: 3.437′




M = 405.8


 


I-47




tR:: 3.442′ M = 405.9


 


I-48




tR:: 3.383′ M = 433.9


 


I-49




tR:: 3.711′ M = 390.8


 


I-50




tR:: 3.816′ M = 455.9


 


I-51




tR:: 3.821′ M = 433.8


 


I-52




tR:: 4.003′ M = 390.7


 


I-53




tR:: 3.968′ M = 403.8


 


I-54




tR:: 3.862′ M = 433.9


 


I-55




tR:: 4.333′ M = 510.1


 


I-56




tR:: 3.176′ M = 398.0


 


I-57




tR:: 2.885′ M = 424.0


 


I-58




tR:: 3.645′ M = 425.9


 


I-59




tR:: 3.794′ M = 435.9


 


I-60




tR:: 3.593′ M = 421.9


 


I-61




tR:: 3.358′ M = 393.8


 


I-62




tR:: 3.704′ M = 407.9


 


I-63




tR:: 3.021′ M = 409.8


 


I-64




tR:: 3.54′ M = 453.9


 


I-65




tR:: 2.83′ M = 448.9


 


I-66




tR:: 3.551′ M = 437.8


 


I-67




tR:: 3.292′ M = 437.8


 


I-68




tR:: 2.895′ M = 465.9


 


I-69




tR:: 4.078′ M = 471.9


 


I-70




tR:: 4.222′ M = 461.9


 


I-71
#-NCH2cyclopropyl
tR:: 3.214′




M = 378.0


 


I-72




tR:: 3.646′ M = 408.1


 


I-73




tR:: 3.328′ M = 380.0


 


I-74




tR:: 3.624′ M = 408.1


 


I-75
#-N-cyclobutyl
tR:: 3.272′




M = 378.0


I-76
#-NH2
tR:: 2.652′




M = 324.0


 


I-77




tR:: 3.417′ M = 394.0


 


I-78
#-N-allyl
tR:: 3.116′




M = 364.0


 


I-79




tR:: 3.359′ M = 440.0


 


I-80




tR:: 2.978′ M = 396.0


 


I-81




tR:: 2.801′ M = 394.0


 


I-82




tR:: 3.028′ M = 426.0


 


I-83




tR:: 2.920′ M = 412.0


 


I-84




tR:: 3.389′ M = 451.9


 


I-85




tR:: 3.422′ M = 393.8


 


I-86




tR:: 3.725′ M = 433.9


 


I-87




tR:: 3.432′ M = 427.)


 


I-88




tR:: 3.443′ M = 446./


 


I-89




tR:: 3.025′ M = 393.8


 


I-90




tR:: 4.21′ M = 353.7


 


I-91




tR:: 3.088′ M = 409.7


 


I-92




tR:: 3.529′ M = 421.9


 


I-93




tR:: 3.9′ M = 451.9


 


I-94




tR:: 3.519′ M = 391.8


 


I-95




tR:: 3.069′ M = 409.8


 


I-96




tR:: 3.29′ M = 465.9


 


I-97




tR:: 3.795′ M = 451.9


 


I-98




tR:: 2.66′ M = 409.8


 


I-99




tR:: 3.130′ M = 352.1


 


I-100




tR:: 3.357′ M = 380.0


 


I-101




tR:: 3.298′ M = 380.0


 


I-102




tR:: 3.527′ M = 394.0


 


I-103




tR:: 2.800′ M = 410.0


 


I-104




tR:: 2.586′ M = 421.0


 


I-105




tR:: 2.508′ M = 437.0


 


I-106




tR:: 2.841′ M = 424.0


 


I-107




tR:: 2.561′ M = 423.1


 


I-108




tR:: 3.933′ M = 404.8


 


I-109




tR:: 3.209′ M = 409.8


 


I-110




tR:: 2.945′ M = 338.1


 


I-111




tR:: 3.280′ M = 366.1


 


I-112




tR:: 3.48′ M = 395.8


 


I-113




tR:: 3.713′ M = 420.1


 


I-114




tR:: 2.888′ M = 370.0


 


I-115




tR:: 3.533′ M = 437.8


 


I-116




tR:: 3.404′ M = 509.1


 


I-117




tR:: 3.040′ M = 408.0


 


I-118




tR:: 3.492′ M = 408.1


 


I-119




tR:: 3.217′ M = 412.0


 


I-120




tR:: 3.101′ M = 400.0


 


I-121




tR:: 3.043′ M = 410.0


 


I-122




tR:: 3.528′ M = 404.8


 


I-123




tR:: 3.489′ M = 407.9


 


I-124




tR:: 2.772′ M = 395.8


 


I-125




tR:: 3.682′ M = 417.9


 


I-126




tR:: 3.207′ M = 480.9


 


I-127




tR:: 3.388′ M = 379.8


 


I-128




tR:: 3.485′ M = 451.9


 


I-129




tR:: 3.209′ M = 409.8


 


I-130




tR:: 2.585′ M = 450.9


 


I-131




tR:: 3.207′ M = 411.9


 


I-132




tR:: 2.675′ M = 422.8


 


I-133




tR:: 3.295′ M = 391.8


 


I-134




tR:: 3.743′ M = 407.8


 


I-135




tR:: 4.034′ M = 441.8


 


I-136




tR:: 3.551′ M = 417.9


 


I-137




tR:: 3.721′ M = 389.8


 


I-138




tR:: 3.509′ M = 441.8


 


I-139




tR:: 3.833′ M = 463.93


 


I-140




tR:: 3.896′ M = 463.9


 


I-141




tR:: 3.038′ M = 425.8


 


I-142




tR:: 3.073′ M = 409.8


 


I-143




tR:: 3.219′ M = 467.9


 


I-144




tR:: 3.619′ M = 493.9


 


I-145




tR:: 3.271′ M = 465.9


 


I-146




tR:: 4.146′ M = 491.9


 


I-147




tR:: 3.632′ M = 414.3


 


I-148




tR:: 3.562′ M = 410.2


 


I-149




tR:: 3.932′ M = 493.9


 


I-150




tR:: 2.663′ M = 465.9


 


I-151




tR:: 3.392′ M = 388.0


 


I-152




tR:: 3.428′ M = 420.0


 


I-153




tR:: 3.308′ M = 420.0


 


I-154




tR:: 3.807′ M = 406.0


 


I-155




tR:: 3.700′ M = 432.1


 


I-156




tR:: 2.471′ M = 395.0


 


I-157




tR:: 3.482′ M = 394.0


 


I-158




tR:: 3.152′ M = 455.9


 


I-159




tR:: 3.972′ M = 419.7


 


I-160




tR:: 3.552′ M = 391.8


 


I-161




tR:: 3.558′ M = 441.9


 


I-162




tR:: 3.296′ M = 391.8


 


I-163




tR:: 3.397′ M = 433.9


 


I-164




tR:: 3.49′ M = 453.9


 


I-165




tR:: 3.432′ M = 405.85


 


I-166




tR:: 3.331′ M = 456.9


 


I-167




tR:: 3.221′ M = 409.8


 


I-168




tR:: 3.165′ M = 409.8


 


I-169




tR:: 3.855′ M = 377.8


 


I-170




tR:: 3.298′ M = 391.8


 


I-171




tR:: 3.823′ M = 395.8


 


I-172




tR:: 3.911′ M = 437.8


 


I-173




tR:: 3.402′ M = 465.9


 


I-174




tR:: 4.207′ M = 479.9


 


I-175




tR:: 3.181′ M = 423.8


 


I-176




tR:: 3.204′ M = 409.8


 


I-177




tR:: 3.463′ M = 398.2


 


I-178




tR:: 3.075′ M = 425.8


 


I-179




tR:: 3.609′ M = 423.82


 


I-180




tR:: 3.733′ M = 479.9


 


I-181




tR:: 4.32′ M = 461.9


 


I-182




tR:: 3.434′ M = 375.8


 


I-183




tR:: 3.74′ M = 479.9


 


I-184




tR:: 3.776′ M = 479.9


 


I-185




tR:: 3.471′ M = 423.9


 


I-186




tR:: 3.518′ M = 391.8


 


I-187




tR:: 3.894′ M = 455.9


 


I-188




tR:: 2.469′ M = 410.8


 


I-189




tR:: 2.469′ M = 410.8


 


I-190




tR:: 3.699′ M = 414.3


 


I-191




tR:: 3.224′ M = 395.8


 


I-192




tR:: 3.253′ M = 376.8


 


I-193




tR:: 3.331′ M = 361.7


 


I-194




tR:: 3.188′ M = 404.0


 


I-195




tR:: 3.452′ M = 394.0


 


I-196




tR:: 3.132′ M = 438.0


 


I-197




tR:: 3.698′ M = 407.9


 


I-198




tR:: 3.882′ M = 417.9


 


I-199




tR:: 4.081′ M = 445.9


 


I-200




tR:: 3.755′ M = 407.9









In Table F, compounds are of the general formula:




wherein RF in the above formula is R1 or R2 

and RF is a propyl (Pr) or an ethyl (Et) and A as indicated in Table F:











TABLE F





I
RF
A
LC/MS







I-201
Et




tR: 2.654′ M = 335.8


 


I-202
Et




tR: 3.123′ M = 398.1


 


I-203
Et




tR: 3.404′ M = 387.0


 


I-204
Pr




tR: 3.613′ M = 401.0


 


I-205
Pr




tR: 2.778′ M = 428.8


 


I-206
Et




tR: 2.922′ M = 414.2


 


I-207
Pr




tR: 3.213′ M = 428.2


 


I-208
Et 




tR: 3.109′ M = 363.0


 


I-209
Et




tR: 3.239′ M = 386.0


 


I-210
Et




tR: 3.255′ M = 410.1


 


I-211
Et




tR: 3.396′ M = 454.0


 


I-212
Et




tR: 3.147′ M = 404.0


 


I-213
Et




tR: 3.281′ M = 420.0


 


I-214
Et




tR: 2.461′ M = 333.1


 


I-215
Et




tR: 3.598′ M = 420.0


 


I-216
Et




tR: 2.778′ M = 429.0


 


I-217
Et




tR: 3.29′ M = 419.8


 


I-218
Et




tR: 2.981′ M = 369.8


 


I-219
Pr




tR: 3.183′ M = 383.8


 


I-220
Et




tR: 3.101′ M = 386.2


 


I-221
Pr




tR: 3.279′ M = 400.2


 


I-222
Et




tR: 3.35′ M = 369.8


 


I-223
Pr




tR: 3.564′ M = 383.8


 


I-224
Et




tR: 3.562′ M = 386.2


 


I-225
Pr




tR: 3.755′ M = 400.2


 


I-226
Et




tR: 3.016′ M = 374.4


 


I-227
Pr




tR: 3.201′ M = 388.4


 


I-228
Et




tR: 3.246′ M = 369.8


 


I-229
Pr




tR: 3.441′ M = 383.8


 


I-230
Et




tR: 3.05′ M = 353.3


 


I-231
Pr




tR: 3.251′ M = 367.3


 


I-232
Et




tR: 2.735′ M = 397.9


 


I-233
Pr




tR: 3.968′ M = 417.3


 


I-234
Et




tR: 3.789′ M = 403.3


 


I-235
Pr




tR: 2.945′ M = 367.6


 


I-236
Et




tR: 2.768′ M = 353.3


 


I-237
Pr




tR: 3.052′ M = 411.2


 


I-238
Et




tR: 2.885′ M = 369.8


 


I-239
Pr




tR: 3.078′ M = 383.8


 


I-240
Et




tR: 3.024′ M = 403.3


 


I-241
Pr




tR: 3.199′ M = 417.3


 


I-242
Pr




tR: 2.884′ M = 346.4


 


I-243
Et




tR: 2.706′ M = 332.3


 


I-244
Pr




tR: 3.377′ M = 416.4


 


I-245
Pr




tR: 3.6′ M = 416.4


 


I-246
Pr




tR: 3.6′ M = 448.8


 


I-247
Pr




tR: 3.295′ M = 414.4


 


I-248
Pr




tR: 3.458′ M = 428.4


 


I-249
Pr




tR: 3.423′ M = 448.8


 


I-250
Pr




tR: 3.125′ M = 412.4


 


I-251
Pr




tR: 3.594′ M = 430.4


 


I-252
Pr




tR: 3.798′ M = 456.5


 


I-253
Pr




tR: 3.252′ M = 426.4


 


I-254
Pr




tR: 3.227′ M = 402.4


 


I-255
Et




tR: 4.007′ M = 419.8


 


I-256
Pr




tR: 4.146′ M = 433.8


 


I-257
Et




tR: 4.094′ M = 454.2


 


I-258
Et




tR: 4.252′ M = 387.7


 


I-259
Et




tR: 4.044′ M = 371.3


 


I-260
Pr




tR: 4.283′ M = 385.3


 


I-261
Et




tR: 3.047′ M = 365.8


 


I-262
Et




tR: 3.577′ M = 387.7


 


I-263
Pr




tR: 3.749′ M = 401.8


 


I-264
Pr




tR: 3.223′ M = 379.8


 


I-265
Pr




tR: 4.456′ M = 401.8


 


I-266
Et




tR: 3.131′ M = 371.3


 


I-267
Pr




tR: 3.353′ M = 385.3


 


I-268
Pr




tR: 3.596′ M = 441.4


 


I-269
Pr




tR: 3.507′ M = 401.8


 


I-270
Pr




tR: 3.513′ M = 415.3


 


I-271
Pr




tR: 3.323′ M = 359.3


 


I-272
Pr




tR: 3.25′ M = 375.4


 


I-273
Pr




tR: 3.396′ M = 391.4


 


I-274
Pr




tR: 2.655′ M = 438.5


 


I-275
Pr




tR: 2.98′ M = 457.5


 


I-276
Pr




tR: 2.878′ M = 413.4


 


I-277
Pr




tR: 2.833′ M = 409.4


 


I-278
Pr




tR: 2.684′ M = 414.4


 


I-279
Pr




tR: 2.493′ M = 404.4


 


I-280
Pr




tR: 2.401′ M = 374.4


 


I-281
Pr




tR: 2.508′ M = 388.4


 


I-282
Pr




tR: 3.139′ M = 389.4


 


I-283
Pr




tR: 2.709′ M = 424.4


 


I-284
Pr




tR: 2.674′ M = 388.4


 


I-285
Pr




tR: 2.597′ M = 402.4


 


I-286
Pr




tR: 2.65′ M = 402.4


 


I-287
Pr




tR: 2.829′ M = 416.4


 


I-288
Pr




tR: 2.958′ M = 373.4


 


I-289
Pr




tR: 2.983′ M = 423.4


 


I-290
Pr




tR: 3.219′ M = 377.4


 


I-291
Pr




tR: 3.111′ M = 345.4


 


I-292
Pr




tR: 3.036′ M = 361.4


 


I-293
Pr




tR: 3.624′ M = 441.4


 


I-294
Pr




tR: 3.767′ M = 437.5


 


I-295
Pr




tR: 3.192′ M = 356.3


 


I-296
Pr




tR: 3.513′ M = 468.4


 


I-297
Pr




tR: 3.508′ M = 441.4


 


I-298
Pr




tR: 3.847′ M = 491.4


 


I-299
Pr




tR: 3.528′ M = 453.5


 


I-300
Pr




tR: 3.561′ M = 453.5


 


I-301
Pr




tR: 3.473′ M = 453.5


 


I-302
Pr




tR: 3.791′ M = 491.4


 


I-303
Pr




tR: 3.86′ M = 507.4


 


I-304
Pr




tR: 3.83′ M = 507.4


 


I-305
Et




tR: 3.308′ M = 387.7


 


I-306
Pr




tR: 3.458′ M = 422.4


 


I-307
Pr




tR: 3.237′ M = 428.5


 


I-308
Pr




tR: 3.083′ M = 413.4


 


I-309
Pr




tR: 2.942′ M = 398.4


 


I-310
Pr




tR: 3.523′ M = 465.4


 


I-311
Pr




tR: 3.121′ M = 398.4


 


I-312
Pr




tR: 2.695′ M = 398.4


 


I-313
Pr




tR: 3.359′ M = 397.4


 


I-314
Pr




tR: 2.731′ M = 431.4


 


I-315
Et




tR: 3.294′ M = 402.4


 


I-316
Et




tR: 3.075′ M = 388.4


 


I-317
Pr




tR: 2.611′ M = 415.4


 


I-318
Pr




tR: 3.184′ M = 401.4


 


I-319
Pr




tR: 3.188′ M = 473.5


 


I-320
Pr




tR: 3.532′ M = 449.5


 


I-321
Pr




tR: 3.501′ M = 397.4


 


I-322
Pr




tR: 2.183′ M = 397.4


 


I-323
Pr




tR: 3.076′ M = 425.5


 


I-324
Pr




tR: 2.668′ M = 440.4


 


I-325
Pr




tR: 3.067′ M = 491.5


 


I-326
Pr




tR: 2.922′ M = 457.5


 


I-327
Pr




tR: 2.876′ M = 411.4


 


I-328
Pr




tR: 2.876′ M = 411.4


 


I-329
Pr




tR: 2.282′ M = 417.4


 


I-330
Pr




tR: 2.132′ M = 403.4


 


I-331
Pr




tR: 2.46′ M = 431.5


 


I-332
Pr




tR: 2.476′ M = 431.5


 


I-333
Pr




tR: 2.597′ M = 445.5


 


I-334
Pr




tR: 2.334′ M = 478.4


 


I-335
Pr




tR: 2.678′ M = 347.3


 


I-336
Pr




tR: 2.867′ M = 331.3


 


I-337
Pr




tR: 3.392′ M = 427.5


 


I-338
Pr




tR: 2.763′ M = 465.5


 


I-339
Pr




tR: 2.182′ M = 419.4


 


I-340
Pr




tR: 2.527′ M = 424.4


 


I-341
Pr




tR: 3.043′ M = 498.4


 


I-342
Pr




tR: 2.994′ M = 375.4


 


I-343
Pr




tR: 4.077′ M = 365.3


 


I-344
Pr




tR: 3.11′ M = 373.4


 


I-345
Pr




tR: 3.161′ M = 370.4


 


I-346
Pr




tR: 2.679′ M = 371.4


 


I-347
Pr




tR: 2.337′ M = 478.5


 


I-348
Pr




tR: 2.995′ M = 483.5


 


I-349
Pr




tR: 2.804′ M = 478.5


 


I-350
Pr




tR: 2.974′ M = 397.4


 


I-351
Pr




tR: 3.144′ M = 472.5


 


I-352
Pr




tR: 3.062′ M = 498.4


 


I-353
Pr




tR: 3.225′ M = 492.5


 


I-354
Pr




tR: 2.843′ M = 444.5


 


I-355
Pr




tR: 3.483′ M = 390.4


 


I-356
Pr




tR: 2.749′ M = 388.4


 


I-357
Pr




tR: 4.394′ M = 400.2


 


I-358
Pr




tR: 4.769′ M = 467.3


 


I-359
Pr




tR: 2.96′ M = 345.4


 


I-360
Pr




tR: 2.794′ M = 444.5


 


I-361
Pr




tR: 3.18′ M = 492.5


 


I-362
Pr




tR: 2.789′ M = 456.5


 


I-363
Pr




tR: 3.094′ M = 472.5


 


I-364
Pr




tR: 2.751′ M = 409.4


 


I-365
Pr




tR: 3.27′ M = 460.5


 


I-366
Pr




tR: 3.155′ M = 357.3


 


I-367
Pr




tR: 3.697′ M = 505.5


 


I-368
Pr




tR: 3.222′ M = 497.3 


 


I-369
Pr




tR: 3.199′ M = 450.3


 


I-370
Pr




tR: 3.227′ M = 405.8


 


I-371
Pr




tR: 3.055′ M = 497.3


 


I-372
Pr




tR: 3.032′ M = 450.3


 


I-373
Pr




tR: 3.01′ M = 405.8


 


I-374
Pr




tR: 3.524′ M = 376.3


 


I-375
Pr




tR: 2.956′ M = 349.3


 


I-376
Pr




tR: 3.582′ M = 379.8


 


I-377
Pr




tR: 3.102′ M = 367.3196


 


I-378
Pr




tR: 3.066′ M = 365.8


 


I-379
Pr




tR: 3.239′ M = 345.4


 


I-380
Pr




tR: 3.445′ M = 359.4


 


I-381
Pr




tR: 3.009′ M = 391.4


 


I-382
Pr




tR: 3.223′ M = 349.3


 


I-383
Pr




tR: 3.203′ M = 399.3


 


I-384
Pr




tR: 3.205′ M = 359.4


 


I-385
Pr




tR: 3.229′ M = 391.4


 


I-386
Pr




tR: 3.257′ M = 359.4


 


I-387
Pr




tR: 3.32′ M = 391.4


 


I-388
Pr




tR: 3.145′ M = 361.4


 


I-389
Pr




tR: 3.325′ M = 395.8


 


I-390
Pr




tR: 3.221′ M = 377.4


 


I-391
Pr




tR: 3.529′ M = 407.4


 


I-392
Pr




tR: 3.471′ M = 437.5


 


I-393
Pr




tR: 3.498′ M = 455.4


 


I-394
Pr




tR: 3.828′ M = 521.5









In Table 3, further examples compounds of the general formula (I)




wherein R1, R2, R3, R4, R5a, R5b, R5c, R5d, A1 and A2 in each case have the meaning given in the corresponding line and wherein A3 and A4 are each CH.



















TABLE 3





I
R1
R2
R3
R4
R5a
R5b
R5c
R5d
A1
A2
LC/MS







I-395
#-CH2CN
H
Br
H
H
CF2
H
H
CH
CH
tR: 3.383′ M = 406.1


I-396
n-butyl
H
Br
H
H
CHF2
H
H
CH
CH
tR: 3.300′ M = 424.0


I-397
#-CH(CH2CH3)2
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.373′ M = 438.0


I-398
cyclohexyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.486′ M = 452.0


I-399
propargyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.119′ M= 405.9


I-400
#-CH2-thiophen-2-yl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.378′ M = 465.9


I-401
ethyl
H
Cl
H
H
CF3
F
F
CH
CH
tR: 4.647′ M = 387.7


I-402
H
H
CF3
A1-NH2
H
CF3
H
H
C
CH
tR: 2.774′ M = 372.7


I-403
2-fluoro-ethyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.018′ M = 414.2


I-404
2,2,2-tRifluoroethyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.952′ M = 450.2


I-405
#-CH2C(O)OC(CH3)3
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.722′ M = 482.3


I-406
propyl
H
Cl
H
F
CF3
H
H
CH
CH
tR: 4.848′ M = 383.8


I-407
ethyl
H
Cl
H
H
1,1,2,2-
H
H
CH
CH
tR: 3.144′ M = 399.8








tetrafluoro-








ethoxy


I-408
propargyl
H
Cl
H
H
1,1,2,2-
H
H
CH
CH
tR: 3.135′ M = 410.1








tetrafluoro-








ethoxy


I-409
propyl
H
Cl
A1-F
Cl
CF3
H
H
C
CH
tR: 4.544′ M = 418.2


I-410
ethyl
H
Cl
H
H
CF3
CH3
H
CH
CH
tR: 3.235′ M = 365.8


I-411
propyl
H
Cl
H
H
CF3
NEt
H
CH
CH
tR: 3.493′ M = 408.8


I-412
cyclopropyl-methyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.165′ M = 424.0


I-413
cyclopentyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.355′ M = 436.0


I-414
#-CH2CH(CH3)2
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.272′ M = 424.0


I-415
#-CH(CH3)CH2CH3
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.244′ M = 424.0


I-416
#-CH(CH3)2
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.098′ M = 412.0


I-417
#-CH(═NH)-
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.384′ M = 437.0



cyclopropyl


I-418
#-CH(═NH)thien-2-yl
H
Br
H
H
CF3
H
H
CH
CH
tR: 4.474′ M = 477.3


I-419
ethyl
H
Cl
H
H
CF3
H
H
CH
CH
tR: 3.213′ M = 369.7


I-420
propyl
H
Cl
H
Cl
CF3
H
H
CH
CH
tR: 4.711′ M = 400.2


I-421
#-CH2-cyclopropyl
H
Cl
H
H
CF3
OCH3
H
CH
CH
tR: 3.412′ M = 407.8


I-422
propyl
H
Cl
H
H
CF3
OCH3
H
CH
CH
tR: 3.386′ M = 395.8


I-423
propyl
H
Cl
H
H
CF3
CH3
H
CH
CH
tR: 3.445′ M = 379.8


I-424
benzyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.595′ M = 458.1


I-425
ethyl
H
Cl
H
H
CHF2
H
H
CH
CH
tR: 2.738′ M = 333.8


I-426
#-CH2-cyclohexyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.635′ M = 466.0


I-427
allyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.070′ M = 410.0


I-428
#-CH2C(CH3)3
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.410′ M = 440.0


I-429
#-CH2-2-furyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.260′ M = 450.0


I-430
propyl
H
Cl
H
CH3
CF3
H
H
CH
CH
tR: 4.892′ M = 379.8


I-431
propyl
H
Cl
A1-F
CH3
CF3
H
H
C
CH
tR: 4.078′ M = 397.8


I-432
propyl
H
F
H
H
C3F7
H
H
CH
CH
tR: 3.428′ M = 449.3


I-433
methyl
methyl
F
H
H
CF3
H
H
CH
CH
tR: 2.537′ M = 335.8


I-434
#-CH(CH3)2
cyclo-
F
H
H
CF3
H
H
CH
CH
tR: 3.120′ M = 389.8




propyl


I-435
H
H
Br
H
H
CF3
H
H
CH
CH
tR: 2.759′ M = 370.0


I-436
ethyl
H
Cl
H
H
OCF3
H
H
CH
CH
tR: 2.966′ M = 368.1


I-437
propyl
H
F
A2-Cl
Cl
CF3
H
H
CH
C
tR: 4.516′ M = 418.2


I-438
n-pentyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.474′ M = 440.0


I-439
#-CH2CH(CH2CH3)2
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.592′ M = 452.0


I-440
3,3,3-trifluoropropyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.366′ M = 463.9


I-441
CH(═NH)phenyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.947′ M = 473.0


I-442
#-CH(CH3)CH(OCH3)2
H
F
A1-F
H
CF3
H
H
C
CH
tR: 2.967′ M = 427.4


I-443
propyl
H
Cl
H
H
CF3
NSO2CH3
H
CH
CH
tR: 3.049′ M = 458.9


I-444
propyl
H
Cl
H
H
CF3
NAc
H
CH
CH
tR: 2.914′ M = 422.8


I-445
ethyl
ethyl
F
H
H
CF3
H
H
CH
CH
tR: 2.903′ M = 363.8


I-446
2,2-difluoroethyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.324′ M = 431.9


I-447
ethyl
methyl
Br
H
H
CF3
H
H
CH
CH
tR: 2.968′ M = 410.0


I-448
#-NH(CO)OC(CH3)3
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.694′ M = 483.0


I-449
propyl
H
Cl
H
H
OCF3
H
H
CH
CH
tR: 3.248′ M = 382.0


I-450
CH(═NH)cyclohexyl
H
Br
H
H
CF3
H
H
CH
CH
tR: 3.566′ M = 477.3


I-451
propyl
H
Cl
H
H
CF3
I
H
CH
CH
tR: 3.971′ M = 491.7









II. Evaluation Of Pesticidal Activity
The activity of the compounds of formula I of the present invention can be demonstrated and evaluated by the following biological test.
B.1 Southern Armyworm (Spodoptera eridania, 2nd instar larvae)
The active compounds were formulated in cyclohexanone as a 10,0000 ppm solution supplied in 1.3 ml ABgene® tubes. These tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone: 50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v). Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. Ten to 11 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at at 25° C. and 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.
In this test, compounds I-1, I-2, I-3, I-4, I-5, I-8, I-10, I-11, I-13, I-16, I-17, I-21, I-23, I-28, I-29, I-30, I-31, I-37, I-38, I-40, I-41, I-46, I-47, I-49, I-53, I-54, I-56, I-57, I-58, I-60, I-61, I-63, I-64, I-67, I-71, I-72, I-73, I-74, I-75, I-77, I-78, I-79, I-80, I-82, I-83, I-84, a85, I-88, I-91, I-94, I-99, I-100, I-101, I-102, I-109, I-110, I-111, I-114, I-117, I-118, I-119, -a120, I-123, I-124, I-125, I-128, I-130, I-132, I-133, I-136, I-143, I-151, I-152, I-153, I-154, I-155, I-157, I-159, I-160, I-161, I-162, I-163, I-167, I-168, I-169, I-170, I-172, I-175, I-176, I-177, I-182, I-183, I-184, I-185, I-186, I-187, I-191, I-192, I-193, I-194, I-195, I-196, I-197, I-198, I-200, I-201, I-202, I-204, I-205, I-206, I-207, I-208, I-210, I-218, I-219, I-222, I-223, I-224, I-225, I-226, I-227, I-229, I-230, I-231, I-233, I-234, I-235, I-236, I-244, I-245, I-246, I-248, I-249, I-250, I-251, I-252, I-253, I-254, I-264, I-266, I-268, I-269, I-270, I-273, I-292, I-295, I-297, I-299, I-300, I-301, I-302, I-303, I-304, I-305, I-306, I-307, I-308, I-309, I-310, I-311, I-312, I-323, I-327, I-329, I-330, I-331, I-332, I-335, I-395, I-396, I-397, I-399, I-400, I-403, I-406, I-407, I-408, I-412, I-413, I-414, I-415, I-416, I-417, I-420, I-421, I-424, I-430, I-431, I-433, I-438, I-440, I-445, I-446, I-447 and I-451 at 300 ppm showed a mortality of at least 50% in comparison with untreated controls.
B.2 Silverleaf Whitefly (Bemisia argentifolii, adult)
The active compounds were formulated in cyclohexanone as a 10,0000 ppm solution supplied in 1.3 ml ABgene® tubes. These tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone: 50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v). Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into a plastic cup and 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and 0.6 cm, nontoxic Tygon® tubing (R-3603) connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid (150-micron mesh polyester screen PeCap from Tetko, Inc.). Test plants were maintained in a growth room at 25° C. and 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants.
In this test, compounds I-11, I-78, I-120, I-121, I-182, I-195, I-196, I-244, I-413 and I-442 at a test concentration of 500 ppm showed a mortality of at least 50% in comparison with untreated controls.
B.3 Colorado potato beetle (Leptinotarsa decemlineata, adult)
The active compounds were formulated in cyclohexanone as a 10,0000 ppm solution supplied in 1.3 ml ABgene® tubes. These tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v). Eggplants were grown 2 plants to a pot and were selected for treatment at the 1st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. The treated foliage was then cut and removed from the pot and placed in a 5-inch Petri dish lined with moistened filter paper. Five beetle larvae were introduced into each Petri dish and the dish was covered by a Petri dish lid. Petri dishes were maintained in a growth room at 25° C. and 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the dishes. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.
In this test, compound I-201 at a test concentration of 300 ppm showed a mortality of at least 50% in comparison with untreated controls.
B.4 Diamondback moth (Plutella xylostella)
The active compound was dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water:acetone. The test solution was prepared at the day of use.
The activity against Plutella xylostella can be tested by the following experiments:
Leaves of Chinese cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dished lined with moist filter paper. Mortality was recorded 24, 72, and 120 hours after treatment.
In this test, compounds I-1, I-4, I-5, I-8, I-10, I-11, I-13, I-16, I-17, I-23, I-28, I-29, I-33, I-36, I-37, I-38, I-46, I-47, I-48, I-51, I-52, I-54, I-56, I-57, I-58, I-60, I-61, I-63, I-71, I-73, I-74, I-75, I-76, I-77, I-78, I-79, I-82, I-83, I-84, I-85, I-88, I-94, I-99, I-100, I-101, I-102, I-103, I-105, I-109, I-110, I-111, I-114, I-117, I-118, I-120, I-121, I-124, I-125, I-131, I-133, I-135, I-136, I-142, I-143, I-151, I-152, I-153, I-154, I-157, I-159, I-160, I-162, I-163, I-169, I-170, I-176, I-177, I-185, I-186, I-187, I-191, I-193, I-194, I-195, I-196, I-198, I-201, I-202, I-204, I-205, I-206, I-207, I-209, I-210, I-211, I-212, I-213, I-215, I-218, I-219, I-21, I-223, I-224, I-225, I-227, I-228, I-229, I-230, I-231, I-233, I-234, I-235, I-236, I-238, I-241, I-61, I-264, I-266, I-267, I-268, I-270, I-272, I-285, I-292, I-296, I-297, I-299, I-300, I-301, I-302, I-303, I-304, I-306, I-307, I-313, I-395, I-396, I-397, I-399, I-403 and I-404 at a test concentration of 500 ppm showed a mortality of at least 50% in comparison with untreated controls.
B.5 Orchid thrips (Dichromothrips corbetti)
Dichromothrips corbetti adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound was diluted to a concentration of 300 ppm (wt compound: vol diluent) in a 1:1 mixture of acetone:water (vol:vol), plus 0.01% vol/vol Kinetic® surfactant. Thrips potency of each compound was evaluated by using a floral-immersion technique. Plastic petri dishes were used as test arenas. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry. Treated flowers were placed into individual petri dishes along with 10-15 adult thrips. The petri dishes were then covered with lids. All test arenas were held under continuous light and a temperature of about 28° C. for duration of the assay. After 4 days, the numbers of live thrips were counted on each flower, and along inner walls of each petri dish. The level of thrips mortality was extrapolated from pre-treatment thrips numbers.
In this test, compounds I-5, I-8, I-29, I-56, I-71, I-100, I-101, I-111, I-124, I-131, I-133, I-162, I-169, I-170, I-201, I-202, I-225, I-227, I-231, I-235, I-242, I-243, I-412, I-434 and I-445 at a test concentration of 500 ppm showed a mortality of at least 50% in comparison with untreated controls.
B.6 Vetch aphid (Megoura viciae)
For evaluating control of vetch aphid (Megoura viciae) through contact or systemic means the test unit consists of 24-well-microtiter plates containing broad bean leaf disks. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the leaf disks at 2.5 μl, using a custom built micro atomizer, at two replications. After application, the leaf disks were air-dried and 5-8 adult aphids placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and incubated at about 23±1° C. and about 50±5% relative humidity for 5 days. Aphid mortality and fecundity was then visually assessed.
In this test, compounds I-11, I-32, I-34, I-35, I-47, I-66, I-78, I-84, I-86, I-87, I-122, I-162, I-164, I-165, I-169, I-170, I-197, I-205, I-217, I-220, I-232, I-233, I-235, I-240, I-241, I-264, I-282, I-330, I-413, I-415, I-418 and I-425 at a test concentration of 800 ppm showed a mortality of at least 50%.
B.7 Green Peach Aphid (Myzus persicae, mixed life stages)
The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).
Bell pepper plants at the first true-leaf stage were infested prior to treatment by placing heavily infested leaves from the main colony on top of the treatment plants. Aphids were allowed to transfer overnight to accomplish an infestation of 30-50 aphids per plant and the host leaves were removed. The infested plants were then sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood, removed, and then maintained in a growth room under fluorescent lighting in a 24-hr photoperiod at about 25° C. and about 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on untreated control plants, was determined after 5 days.
In this test, compounds I-29, I-32, I-33, I-35, I-57, I-60, I-77, I-100, I-101, I-102, I-105, I-109, I-114, I-118, I-119, I-120, I-150, I-162, I-165, I-169, I-191, I-195, I-217, I-218, I-221, I-223, I-225, I-227, I-228, I-235, I-239, I-240, I-241, I-270, I-271, I-272, I-273, I-274, I-279, I-280, I-283, I-284, I-286, I-288, I-289, I-290, I-291, I-292, I-296, I-332, I-335, I-402, I-415, I-418, I-425, I-436 and I-448 at a test concentration of 800 ppm showed a mortality of at least 50%.
B.8 Boll weevil (Anthonomus grandis)
For evaluating control of boll weevil (Anthonomus grandis) the test unit consists of 24-well-microtiter plates containing an insect diet and 20-30 A. grandis eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 20 μl, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 23±1° C. and about 50±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.
In this test, compounds I-10, I-11, I-13, I-17, I-28, I-29, I-31, I-34, I-37, I-38, I-40, I-41, I-46, I-58, I-60, I-61, I-64, I-71, I-73, I-77, I-78, I-79, I-80, I-82, I-83, I-100, I-101, I-102, I-108, I-109, I-111, I-113, I-114, I-116, I-119, I-120, I-121, I-124, I-132, I-133, I-152, I-153, I-154, I-157, I-159, I-162, I-163, I-169, I-182, I-191, I-193, I-194, I-195, I-199, I-201, I-202, I-205, I-207, I-208, I-211, I-218, I-219, I-221, I-222, I-223, I-25, I-227, I-229, I-230, I-231, I-232, I-233, I-234, I-235, I-236, I-240, I-243, I-255, I-261, I-264, I-267, I-269, I-271, I-272, I-273, I-277, I-280, I-281, I-282, I-283, I-284, I-285, I-289, I-290, I-291, I-92, I-295, I-330, I-335, I-336, I-395, I-396, I-397, I-399, I-403, I-406, I-412, I-415, I-416, I-420, I-24, I-425, I-427, I-428, I-430, I-431, I-435, I-438 and I-449 at a test concentration of 800 ppm showed a mortality of at least 50%.
B. 9 Mediterranean fruitfly (Ceratitis capitata)
For evaluating control of Mediterranean fruitfly (Ceratitis capitata) the test unit consisted of microtiter plates containing an insect diet and 50-80 C. capitata eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μl, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 28±1° C. and about 80±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.
In this test, compounds I-10, I-11, I-12, I-13, I-14, I-16, I-17, I-19, I-28, I-29, I-34, I-37, I-38, I-45, I-46, I-47, I-49, I-56, I-57, I-61, I-64, I-71, I-72, I-73, I-74, I-75, I-77, I-78, I-79, I-80, I-81, I-82, I-83, I-87, I-98, I-99, I-100, I-101, I-102, I-105, I-107, I-109, I-111, I-114, I-115, I-117, I-118, I-119, I-120, I-121, I-125, I-133, I-151, I-152, I-153, I-154, I-155, I-157, I-159, I-162, I-163, I-169, I-182, I-191, I-193, I-195, I-196, I-199, I-201, I-202, I-205, I-206, I-207, I-208, I-209, I-210, I-213, I-215, I-218, I-219, I-221, I-222, I-223, I-224, I-225, I-226, I-227, I-228, I-229, I-230, I-231, I-233, I-234, I-235, I-236, I-237, I-239, I-241, I-255, I-257, I-264, I-267, I-269, I-270, I-272, I-276, I-295, I-330, I-331, I-332, I-335, I-395, I-396, I-397, I-399, I-400, I-403, I-404, I-406, I-407, I-408, I-409, I-412, I-414, I-415, I-416, I-417, I-418, I-420, I-424, I-427, I-431, I-434, I-437, I-438, I-440, I-441, I-445, I-446, I-447, I-448 and I-449 at a test concentration of 800 ppm showed a mortality of at least 50%.
B.10 Tobacco budworm (Heliothis virescens)
For evaluating control of tobacco budworm (Heliothis virescens) the test unit consists of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 μl, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 28±1° C. and about 80±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.
In this test, compounds I-8, I-10, I-11, I-12, I-13, I-16, I-17, I-19, I-28, I-29, I-32, I-34, I-37, I-38, I-39, I-40, I-41, I-46, I-47, I-49, I-56, I-57, I-60, I-61, I-63, I-64, I-71, I-72, I-73, I-74, I-75, I-76, I-77, I-78, I-79, I-80, I-82, I-83, I-84, I-85, I-99, I-100, I-101, I-102, I-109, I-111, I-114, I-115, I-116, I-117, I-118, I-119, I-120, I-121, I-122, I-124, I-125, I-126, I-130, I-132, I-133, I-151, I-152, I-153, I-154, I-157, I-158, I-159, I-160, I-161, I-162, I-163, I-168, I-169, I-182, I-191, I-193, I-194, I-195, I-196, I-197, I-199, I-200, I-201, I-202, I-204, I-205, I-206, I-207, I-208, I-209, I-210, I-212, I-215, I-216, I-218, I-219, I-221, I-222, I-223, I-224, I-225, I-226, I-227, I-228, I-229, I-230, I-231, I-232, I-233, I-234, I-235, I-236, I-237, I-238, I-239, I-241, I-255, I-256, I-257, I-261, I-264, I-266, I-267, I-269, I-270, I-271, I-272, I-273, I-280, I-282, I-283, I-284, I-287, I-290, I-291, I-292, I-295, I-329, I-330, I-331, I-332, I-335, I-395, I-396, I-397, I-399, I-400, I-403, I-404, I-405, I-406, I-407, I-408, I-409, I-412, I-413, I-414, I-415, I-416, I-420, I-424, I-425, I-427, I-430, I-431, I-433, I-435, I-436, I-437, I-438, I-439, I-440, I-445, I-446, I-447, I-448, I-449 at a test concentration of 800 ppm showed a mortality of at least 50%.

## Claims

1. A method for controlling or combating invertebrate pests attack or infestation which method comprises treating the pests, their food supply, their habitat, their breeding ground, the plant, the plant propagation material, soil, area, material or environment in which the pests are growing or may grow, with a pesticidally effective amount of a compound of the formula (I)



wherein
A1, A2, A3 and A4 are N, NX or CR4 wherein X is a lone pair or O, with the proviso that at most three of A1, A2, A3 and A4 are N or NX;
R1, R2 are selected independently from one another from the group consisting of hydrogen, CN, NO2, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, NR8R9, N═C(R6)2, C(═O )R6, C(═S)R6, C(═NR8)R6 
 and a 3-, 4-, 5-, 6- or 7- membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially saturated,
comprises 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, wherein the nitrogen and/or the sulfur atom(s) may be oxidized,
is unsubstituted or substituted with one to five R10, and
wherein one or two CH2 groups in said heterocyclic ring may be replaced by one or two C═O groups;


R3 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5,C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially saturated,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said heterocyclic ring may be replaced by one or two C═O groups;


each R4 is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


 or two radicals R4 bound on adjacent carbon atoms together form a group selected from the group consisting of —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—,
wherein in each of the above group,
one to five hydrogen atoms independently of each other may be replaced by one to five substituents selected from the group consisting of halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or
one or two CH2 groups of the above groups may be replaced by one or two C═O groups;


R5a is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or R5a may form together with the adjacent carbon atom R5b a 5- or 6-membered ring which is at least substituted with one halogen;
R5b is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy, wherein each mentioned radical
is substituted with at least one halogen,
may be further partially or fully halogenated, and
may be substituted with one to five radicals R6;

 or R5b may form together with the adjacent carbon atom R5c or R5a a 5- or 6-membered ring which is substituted with at least one halogen;
R5c is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)OR7, C(═S)OR7, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or R5c may form together with the adjacent carbon atom R5b or R5d a 5- or 6-membered ring which is substituted with at least one halogen in case of R5b being involved;
R5d is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, S(O)mN(R8)R9, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or R5d may form together with the adjacent carbon atom R5c or with R1 or R2 a 5- or 6-membered ring;
R6 is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or two vicinally bound radicals R6 together form a group selected from ═C(Rc)2, ═S(O)mRo, ═S(O)mN(Rn)2, ═NRn and ═NN(Rn)2;
R7 is selected independently from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


with the proviso that R7 is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
R8, R9 are selected independently from one another and independently of each occurrence from the group consisting of hydrogen, CN, NO2, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2 phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


R10 is selected independently from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with one to five radicals selected independently from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or unsaturated,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals selected independently from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;


 or two radicals R10 bound on adjacent atoms together form a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—,
wherein in each of the above groups,
one to five hydrogen atoms independently of each other may be replaced by one to five substituents selected from the group consisting of halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or
one or two or more CH2 groups of the above groups may be replaced by one or two C═O groups;

R11, R12 are selected independently of each other and independently of each occurrence from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl;
Rc is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;


Ro is selected independently from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

with the proviso that Ro is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
Rn is selected independently from the group consisting of hydrogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;


m is independently 0, 1 or 2;
p is 0, 1, 2, 3 or 4;

or enantiomers or diastereoisomers thereof or their agriculturally or veterinarily acceptable salts, or a composition comprising at least one compound of formula I.

2. The method according to claim 1, wherein R5b is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy, wherein each mentioned radical is at least substituted with one halogen.

3. The method according to claim 1, wherein R3 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkoxy, C3-C6-halocycloalkoxy, Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═(R6)2, C(═O)R6, C(═S)R6 and C(═NR8)R6.

4. The method according to claim 1, wherein
R5b is selected from the group consisting of C1-C6-haloalkyl and C1-C6-haloalkoxy;
R3 is selected from the group consisting of hydrogen, halogen, CN, NO2, C(═NR8)R6, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkoxy and C3-C6-halocycloalkoxy.

5. The method according to claim 1, wherein
R5b is CF3;
R3 is halogen;
A1, A2, A3 and A4 are CR4;
R5c and R5d are independently from one another hydrogen, halogen, C1-C6-alkyl or C1-C6-haloalkyl;
R5a and each R4 are independently from one another hydrogen, halogen, CN, NO2, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy or C1-C6-cycloalkoxy.

6. The method according to claim 1, wherein
R5b is CF3;
R3 is halogen;
A1, A2, A3 and A4 are CR4;
R5c and R5d are hydrogen;
R5a and each R4 are independently from one another hydrogen, halogen, C1-C6-alkyl, or C1-C6-haloalkyl.

7. A method for protecting plants or plant propagation materials from attack or infestation by invertebrate pests, which method comprises treating the plants or the plant propagation materials or the materials, surfaces or spaces in which they grow with a pesticidally effective amount of a compound of formula (I)



wherein
A1, A2, A3 and A4 are N, NX or CR4 wherein X is a lone pair or O, with the proviso that at most three of A1, A2, A3 and A4 are N or NX;
R1, R2 are selected independently from one another from the group consisting of hydrogen, CN, NO2, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, NR8R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially saturated,
comprises 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, wherein the nitrogen and/or the sulfur atom(s) may be oxidized,
is unsubstituted or substituted with one to five R10, and
wherein one or two CH2 groups in said heterocyclic ring may be replaced by one or two C═O groups;


R3 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially saturated,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said heterocyclic ring may be replaced by one or two C═O groups;


each R4 is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


 or two radicals R4 bound on adjacent carbon atoms together form a group selected from the group consisting of —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—,
wherein in each of the above group,
one to five hydrogen atoms independently of each other may be replaced by one to five substituents selected from the group consisting of halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or
one or two CH2 groups of the above groups may be replaced by one or two C═O groups;


R5a is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or R5a may form together with the adjacent carbon atom R5b a 5- or 6-membered ring which is at least substituted with one halogen;
R5b is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy, wherein each mentioned radical
is substituted with at least one halogen,
may be further partially or fully halogenated, and
may be substituted with one to five radicals R6;

 or R5b may form together with the adjacent carbon atom R5c or R5a a 5- or 6-membered ring which is substituted with at least one halogen;
R5c is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)OR7, C(═S)OR7, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or R5c may form together with the adjacent carbon atom R5b or R5d a 5- or 6-membered ring which is substituted with at least one halogen in case of R5b being involved;
R5d is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, S(O)mN(R8)R9, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or R5d may form together with the adjacent carbon atom R5c or with R1 or R2 a 5- or 6-membered ring;
R6 is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or two vicinally bound radicals R6 together form a group selected from ═C(Rc)2, ═S(O)mRo, ═S(O)mN(Rn)2, ═NRn and ═NN(Rn)2;
R7 is selected independently from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


with the proviso that R7 is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
R8, R9 are selected independently from one another and independently of each occurrence from the group consisting of hydrogen, CN, NO2, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2 phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


R10 is selected independently from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with one to five radicals selected independently from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or unsaturated,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals selected independently from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;


 or two radicals R10 bound on adjacent atoms together form a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—,
wherein in each of the above groups,
one to five hydrogen atoms independently of each other may be replaced by one to five substituents selected from the group consisting of halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or
one or two or more CH2 groups of the above groups may be replaced by one or two C═O groups;

R11, R12 are selected independently of each other and independently of each occurrence from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl;
Rc is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;


Ro is selected independently from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

with the proviso that Ro is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
Rn is selected independently from the group consisting of hydrogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;


m is independently 0, 1 or 2;
p is 0, 1, 2, 3 or 4;

or enantiomers or diastereoisomers thereof or their agriculturally or veterinarily acceptable salts;
or a composition comprising the compound.

8. The method according to claim 7, wherein R5b is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy, wherein each mentioned radical is at least substituted with one halogen.

9. The method according to claim 7, wherein R3 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkoxy, C3-C6-halocycloalkoxy, Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═(R6)2, C(═O)R6, C(═S)R6 and C(═NR8)R6.

10. The method according to claim 7, wherein
R5b is selected from the group consisting of C1-C6-haloalkyl and C1-C6-haloalkoxy;
R3 is selected from the group consisting of hydrogen, halogen, CN, NO2, C(═NR8)R6, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkoxy and C3-C6-halocycloalkoxy.

11. The method according to claim 7, wherein
R5b is CF3;
R3 is halogen;
A1, A2, A3 and A4 are CR4;
R5c and R5d are independently from one another hydrogen, halogen, C1-C6-alkyl or C1-C6-haloalkyl;
R5a and each R4 are independently from one another hydrogen, halogen, CN, NO2, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy or C1-C6-cycloalkoxy.

12. The method according to claim 7, wherein
R5b is CF3;
R3 is halogen;
A1, A2, A3 and A4 are CR4;
R5c and R5d are hydrogen;
R5a and each R4 are independently from one another hydrogen, halogen, C1-C6-alkyl, or C1-C6-haloalkyl.

13. A method for combating invertebrate pests attack or infestation which method comprises treating the pests, their food supply, their habitat, their breeding ground, the plant, the plant propagation material, soil, area, material or environment in which the pests are growing or may grow, with a pesticidally effective amount of at least one compound of the formula I as defined in claim 1 or a composition comprising it.

14. Plant propagation material treated with the compound of claim 1 or a composition comprising the compound.

15. Seeds treated with a compound of claim 1 in an amount of from 0.1 g to 10 kg per 100 kg of seed.

16. A method for treating, controlling, preventing or protecting an animal from infestation or infection by invertebrate pests which comprises bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula I as defined in claim 1.

17. A compound of formula (I)



wherein
A1, A2, A3 and A4 are N, NX or CR4 wherein X is a lone pair or O, with the proviso that at most three of A1, A2, A3 and A4 are N or NX;
R1, R2 are selected independently from one another from the group consisting of hydrogen, CN, NO2, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12,OR7, S(O)mR7, NR8R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6 
 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially saturated,
comprises 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, wherein the nitrogen and/or the sulfur atom(s) may be oxidized,
is unsubstituted or substituted with one to five R10, and
wherein one or two CH2 groups in said heterocyclic ring may be replaced by one or two C═O groups;


R3 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially saturated,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said heterocyclic ring may be replaced by one or two C═O groups;


each R4 is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


 or two radicals R4 bound on adjacent carbon atoms together form a group selected from the group consisting of —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—,
wherein in each of the above group,
one to five hydrogen atoms independently of each other may be replaced by one to five substituents selected from the group consisting of halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or
one or two CH2 groups of the above groups may be replaced by one or two C═O groups;


R5a is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or R5a may form together with the adjacent carbon atom R5b a 5- or 6-membered ring which is at least substituted with one halogen;
R5b is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy, wherein each mentioned radical
is substituted with at least one halogen,
may be further partially or fully halogenated, and
may be substituted with one to five radicals R6;

 or R5b may form together with the adjacent carbon atom R5c or R5a a 5- or 6-membered ring which is substituted with at least one halogen;
R5c is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)OR7, C(═S)OR7, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or R5c may form together with the adjacent carbon atom R5b or R5d a 5- or 6-membered ring which is substituted with at least one halogen in case of R5b being involved;
R5d is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;

 Si(R11)2R12, OR7, S(O)mR7, S(O)mN(R8)R9, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or R5d may form together with the adjacent carbon atom R5c or with R1 or R2 a 5- or 6-membered ring;
R6 is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


or two vicinally bound radicals R6 together form a group selected from ═C(Rc)2, ═S(O)mRo, ═S(O)mN(Rn)2, ═NRn and ═NN(Rn)2;
R7 is selected independently from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


with the proviso that R7 is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
R8, R9 are selected independently from one another and independently of each occurrence from the group consisting of hydrogen, CN, NO2, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2 phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;


R10 is selected independently from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;

 Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with one to five radicals selected independently from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;

 and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or unsaturated,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals selected independently from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;


 or two radicals R10 bound on adjacent atoms together form a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—,
wherein in each of the above groups,
one to five hydrogen atoms independently of each other may be replaced by one to five substituents selected from the group consisting of halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or
one or two or more CH2 groups of the above groups may be replaced by one or two C═O groups;

R11, R12 are selected independently of each other and independently of each occurrence from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl;
Rc is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;


Ro is selected independently from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

with the proviso that Ro is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
Rn is selected independently from the group consisting of hydrogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;


m is independently 0, 1 or 2;
p is 0, 1, 2, 3 or 4;

or enantiomers or diastereoisomers thereof or their agriculturally or veterinarily acceptable salts,
with the exception of 2-[4-[2-aminoethyamino]-7-trifluoromethyl-quinazolin-2-yl]-phenol, and the salts and N-oxides thereof.

18. The compound of claim 13, wherein R5b is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy, wherein each mentioned radical is at least substituted with one halogen.

19. The compound of claim 13, wherein R3 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkoxy, C3-C6-halocycloalkoxy, Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═(R6)2, C(═O)R6, C(═S)R6 and C(═NR8)R6.

20. The compound of claim 13, wherein
R5b is selected from the group consisting of C1-C6-haloalkyl and C1-C6-haloalkoxy;
R3 is selected from the group consisting of hydrogen, halogen, CN, NO2, C(═NR8)R6, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkoxy and C3-C6-halocycloalkoxy.

21. The compound of claim 13, wherein
R5b is CF3;
R3 is halogen;
A1, A2, A3 and A4 are CR4;
R5c and R5d are independently from one another hydrogen, halogen, C1-C6-alkyl or C1-C6-haloalkyl;
R5a and each R4 are independently from one another hydrogen, halogen, CN, NO2, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy or C1-C6-cycloalkoxy.

22. The compound of claim 13, wherein
R5b is CF3;
R3 is halogen;
A1, A2, A3 and A4 are CR4;
R5c and R5d are hydrogen;
R5a and each R4 are independently from one another hydrogen, halogen, C1-C6-alkyl, or C1-C6-haloalkyl.