Pesticidally active heterocyclic derivatives with sulfur-containing substituents

Abstract

Compounds having the formula (I), wherein the substituents are as defined in claim 1. Furthermore, the present invention relates to agrochemical compositions comprising the compounds of formula (I), to the preparation of these compositions, and to the use of these compounds or compositions in agriculture or horticulture for combating, preventing or controlling animal pests, these animal pests include the representatives of arthropods and in particular insects, mollusks, nematodes or acarids.

Description

[0001] The present invention relates to pesticidally active, in particular insecticidal, heterocyclic derivatives containing a sulphur substituent, to processes for their preparation, to compositions comprising those compounds and to their use for controlling animal pests, including arthropods and in particular insects or representatives of the order Acarina.

[0002] Heterocyclic derivatives containing sulfur substituents are known and are described, for example, in WO 2016 / 129684, WO 2016 / 162318, WO 2017 / 061497, WO 2017 / 155103, JP 2018 / 024657, JP 2018 / 024658, JP 2018 / 027943, JP 2018 / 030834, JP 2018 / 070585, JP 2018 / 177759, WO 2018 / 050825, WO 2018 / 052136, WO 2018 / 124128, WO 2018 / 199210, JP 2019 / 043944, JP 2019 / 182855, JP 2020 / 111539、WO 2019 / 038195、WO 2019 / 068572、WO 2019 / 175045、WO 2019 / 175046、WO 2019 / 201921、JP 2020 / 169215、WO 2020 / 053282、WO 2020 / 158889、WO 2020 / 171077、WO 2020 / 203763、JP 2021 / 102584、WO 2021 / 033141、WO 2021 / 099240、WO 2021 / 140122、WO 2021 / 141106、WO 2022 / 049141、WO 2022 / 049144 and WO 2022 / 071428.

[0003] It has now been surprisingly found that certain novel sulphur-containing phenyl and pyridyl derivatives attached to a chromenone moiety possess advantageous properties as pesticides.

[0004] Therefore, the present invention provides compounds having formula I,

[0005]

[0006] in

[0007] R8 and R9 are independently of one another halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, and C1-C4 alkylsulfonyl; or R8 and R9 together form a group -O-CF2-O-;

[0008] Q is a group selected from the group consisting of formulae Qa, Qb and Qc

[0009]

[0010] The arrows indicate the points of attachment to the double ring;

[0011] A, A1 and A2 are independently CH or N;

[0012] X is S, SO, or SO2;

[0013] R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl;

[0014] R2, R3, R4 and R5 are independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted by cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, -N(R 10 R 11 ), or -N(R 10 )C(=O)R 11 ;

[0015] R 10 and R 11 are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl;

[0016] R6 and R7 are independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted by cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy or -N(R 12 )C(=O)R 13 ;and

[0017] R 12 and R 13are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl.

[0018] The present invention also provides agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compound of formula I.

[0019] Compounds of formula I with at least one basic center can form acid addition salts, for example, with strong inorganic acids (such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid or hydrohalic acids), strong organic carboxylic acids (such as unsubstituted or, for example, halogen-substituted C1-C4-alkanecarboxylic acids, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid), or organic sulfonic acids (such as unsubstituted or, for example, halogen-substituted C1-C4-alkanesulfonic acids or arylsulfonic acids, for example methanesulfonic acid or p-toluenesulfonic acid). Compounds of formula I having at least one acidic group can form salts, for example, with bases, for example mineral salts, such as alkali metal or alkaline earth metal salts, for example sodium salts, potassium salts or magnesium salts; or with ammonia or organic amines (such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethylamine, diethylamine, triethylamine or dimethylpropylamine, or mono-, di- or trihydroxy lower alkylamines, for example monoethanolamine, diethanolamine or triethanolamine).

[0020] In each case, the compounds of formula (I) according to the invention are in free form, in an oxidized form (such as an N-oxide) or in the form of a salt (for example an agronomically usable salt).

[0021] N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. They are described, for example, by A. Albini and S. Pietra in 1991 in the book "Heterocyclic N-oxides", published by CRC Press, Boca Raton.

[0022] The compounds of formula I according to the invention also include hydrates which may be formed during salt formation.

[0023] When substituents are indicated as themselves being further substituted, this means that they carry one or more identical or different substituents, for example one to four substituents. Typically, there are no more than three such optional substituents at the same time. Preferably, there are no more than two such substituents (that is, the group is replaced by one or two of the indicated substituents) at the same time. When additional substituents are larger groups such as cycloalkyl or phenyl, it is most preferred that there is only one such optional substituent. When a group is indicated as being replaced by, for example, an alkyl, this includes those groups that are a part of other groups, for example the alkyl in an alkylthio group.

[0024] As used herein, the term "aryl" refers to an unsaturated aromatic carbocyclic group having 6 to 10 ring carbon atoms, which has a single ring (e.g., phenyl) or multiple condensed (fused) rings, at least one of which is aromatic (e.g., indanyl, naphthyl). Preferred aryl groups include phenyl, naphthyl, etc., which are optionally substituted with up to three substituents; preferably, the aryl group is phenyl, which is optionally substituted with up to three substituents.

[0025] As used herein, the term "C1-C n “Alkyl” refers to a saturated straight or branched hydrocarbon group having 1 to n carbon atoms attached via any carbon atom, for example, any of the following groups: methyl, ethyl, n-propyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 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.

[0026] As used herein, the term "C1-C n“Haloalkyl” refers to a linear or branched saturated alkyl group having 1 to n carbon atoms (as mentioned above) attached via any carbon atom, wherein some or all of the hydrogen atoms in these groups may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., for example, any of the following: chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 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, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl The term "Ci-C2-fluoroalkyl" shall mean a C1-C2-alkyl group having 1, 2, 3, 4, or 5 fluorine atoms, such as difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, or pentafluoroethyl.

[0027] As used herein, the term "C1-C n "Alkoxy" refers to a straight-chain or branched saturated alkyl group having 1 to n carbon atoms (as mentioned above) attached via an oxygen atom, i.e., for example, any of the following: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy.

[0028] As used herein, the term "C1-C n "Haloalkoxy" refers to the C1-C nAlkoxy groups, which are partially or fully substituted by fluorine, chlorine, bromine and / or iodine, i.e., for example, any one of the following: chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 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 , pentafluoroethoxy, 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, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, or 4-bromobutoxy.

[0029] As used herein, the term "C1-C n "Alkylsulfanyl" refers to a linear or branched saturated alkyl group having 1 to n carbon atoms (as mentioned above) attached via a sulfur atom, i.e., for example, any of the following: methylthio, ethylthio, n-propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio.

[0030] As used herein, the term "C1-C n “Alkylsulfinyl” refers to a straight-chain or branched saturated alkyl group having 1 to n carbon atoms (as mentioned above) attached via the sulfur atom of the sulfinyl group, i.e., for example, any one of the following: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethyl-sulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethyl-ethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methyl-butylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl or 1-ethylpropylsulfinyl.

[0031] As used herein, the term "C1-C n"Alkylsulfonyl" refers to a straight-chain or branched saturated alkyl group having 1 to n carbon atoms (as mentioned above) attached via the sulfur atom of the sulfonyl group, i.e., for example, any of the following: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or tert-butylsulfonyl.

[0032] As used herein, the term "C1-C n "Haloalkylsulfanyl" refers to the C1-C n Alkylthio groups which are partially or fully substituted by fluorine, chlorine, bromine and / or iodine, i.e., for example, any one of the following: fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, or 4-bromobutylthio.

[0033] The term "C1-C n "Haloalkylsulfinyl" and "C1-C n "Haloalkylsulfonyl" refers to the above groups, but wherein the sulfur is in oxidation state 1 or 2, respectively.

[0034] As used herein, the term "C1-C n "Cyanoalkyl" refers to a straight-chain or branched saturated alkyl group having 1 to n carbon atoms (as mentioned above) substituted by a cyano group, for example, cyanomethylene, cyanoethylene, 1,1-dimethylcyanomethyl, cyanomethyl, cyanoethyl, cyanoisopropyl and 1-dimethylcyanomethyl.

[0035] The term "C1-C n "Cyanoalkoxy" refers to a straight-chain or branched saturated cyanoalkyl group (as mentioned above) having 1 to n carbon atoms attached via an oxygen atom.

[0036] As used herein, the term "C3-C6 cycloalkyl" refers to a 3-membered to 6-membered cycloalkyl group, such as cyclopropane, cyclobutane, cyclopropane, cyclopentane, and cyclohexane.

[0037] As used herein, in terms such as "C3-C n The suffix "-C1-C" after "cycloalkyl" n Alkyl" (wherein n is an integer from 1 to 6) refers to a C3-C n A cycloalkyl-substituted straight-chain or branched saturated alkyl group. n Cycloalkyl-C1-C n Examples of alkyl groups are eg cyclopropylmethyl.

[0038] As used herein, the term "C3-C6 cycloalkyl" monosubstituted by cyano refers to a 3- to 6-membered cycloalkyl group (as mentioned above) substituted by cyano. An example of a C3-C6 cycloalkyl monosubstituted by cyano is 1-cyanocyclopropyl.

[0039] Halogen is typically fluorine, chlorine, bromine or iodine. This also applies correspondingly to halogen in combination with other meanings, such as haloalkyl.

[0040] As listed below, certain embodiments according to the present invention are provided.

[0041] Example 1 provides a compound of formula I as defined above, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

[0042] Example 2 provides the compound according to Example 1 (wherein Q is Qa) and having X, R1, R2, R3, R8, R9, R 10 and R 11 The preferred value of the compound or its agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide.

[0043] Example 3 provides the compound according to Example 1 (wherein Q is Qb) and having X, R1, R4, R5, R8, R9, R 10 and R 11 The preferred value of the compound or its agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide.

[0044] Example 4 provides the compound according to Example 1 (wherein Q is Qc) and having A, A1, A2, X, R1, R6, R7, R8, R9, R 12 and R 13 The preferred value of the compound or its agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide.

[0045] Regarding Examples 1-4, X, R1, A, A1, A2, R2, R3, R4, R5, R6, R7, R8, R9, R10 、R 11 、R 12 and R 13 The preferred values ​​of are listed below in any combination:

[0046] Preferably, X is S or SO2.

[0047] Most preferably, X is SO2.

[0048] Preferably, R1 is C1-C4 alkyl or cyclopropyl-C1-C4 alkyl.

[0049] More preferably, R1 is ethyl or cyclopropylmethyl.

[0050] Most preferably, R1 is ethyl.

[0051] Preferably, R2 and R3 are independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted by cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, or -N(R 10 )C(=O)R 11 .

[0052] More preferably, R2 and R3 are independently of each other hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropoxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0053] It is also preferred that R2 and R3 are independently of one another hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0054] It is further preferred that R2 is hydrogen and R3 is hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl); or

[0055] R3 is hydrogen and R2 is chloro, bromo, iodo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0056] Even more preferably, R2 is hydrogen and R3 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or

[0057] R3 is hydrogen and R2 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0058] Most preferably, R2 is hydrogen and R3 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or

[0059] R3 is hydrogen and R2 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0060] Preferably, R4 and R5 are independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted by cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, or -N(R 10 )C(=O)R 11 .

[0061] More preferably, R4 and R5 are independently of each other hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropoxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0062] It is also preferred that R4 and R5 are independently of one another hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0063] Further preferred is when R4 is hydrogen and R5 is hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl); or

[0064] R5 is hydrogen and R4 is chloro, bromo, iodo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0065] Even more preferably, R4 is hydrogen and R5 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or

[0066] R5 is hydrogen and R4 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0067] Most preferably, R4 is hydrogen and R5 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN; or

[0068] R5 is hydrogen and R4 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN.

[0069] Hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl

[0070] Preferably, R 10 and R 11 are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl (preferably cyclopropyl).

[0071] More preferably, R 10 and R 11 are independently hydrogen or methyl.

[0072] Most preferably, R 10 is hydrogen or methyl, and R 11 It's methyl.

[0073] Preferably, A is CH or N.

[0074] Most preferably, A is N.

[0075] Preferably, A1 is CH or N.

[0076] Preferably, A2 is CH or N.

[0077] It is also preferred that A1 is CH and A2 is N.

[0078] It is also preferred that A1 is N and A2 is CH.

[0079] It is further preferred that both A1 and A2 are N.

[0080] Most preferably, both A1 and A2 are CH.

[0081] Preferably, R6 and R7 are independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted by cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, or -N(R12 )C(=O)R 13 .

[0082] More preferably, R6 and R7 are independently of each other hydrogen, chlorine, bromine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropyloxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0083] It is also preferred that R6 and R7 are independently of one another hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0084] It is further preferred that R6 is hydrogen and R7 is hydrogen, chloro, bromo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl); or

[0085] R7 is hydrogen and R6 is chloro, bromo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0086] Even more preferably, R6 is hydrogen and R7 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or

[0087] R7 is hydrogen and R6 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0088] Most preferably, R6 is hydrogen and R7 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN; or

[0089] R7 is hydrogen and R6 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN.

[0090] Preferably, R 12 and R 13 are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl (preferably cyclopropyl).

[0091] More preferably, R 12 and R 13 are independently hydrogen or methyl.

[0092] Most preferably, R 12 is hydrogen or methyl, and R 13 It's methyl.

[0093] R8 and R9 are independently of one another halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0094] More preferably, R8 and R9 are independently of each other halogen, trifluoromethyl, 1,1-difluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl, or aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, trifluoromethyl, -OCHF2, -OCF3, trifluoromethylsulfanyl, trifluoromethylsulfinyl and trifluoromethylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0095] Even more preferably, R8 and R9 are independently of one another fluoro, chloro, bromo, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, or 4-F-phenyl; or R8 and R9 together form a group -O-CF2-O-.

[0096] Most preferably, R8 is hydrogen and R9 is fluoro, chloro, bromo, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl;

[0097] or R9 is hydrogen and R8 is fluoro, chloro, bromo, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl;

[0098] Alternatively, R8 and R9 together form a group -O-CF2-O-.

[0099] As described below, further embodiments according to the present invention are provided.

[0100] A preferred group of compounds having formula I is represented by the following: Compounds having formula I-1

[0101]

[0102] Among them, X, R1, R2, R3, R8, R9, R 10 and R 11 is as defined above under formula I, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula 1-1.

[0103] In a preferred group of compounds of formula I-1, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; X is S or SO2; R2 and R3 are independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, or -N(R 10 )C(=O)R 11 ; and R 10 and R 11 are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl (preferably cyclopropyl); preferably, R 10 and R 11 are independently hydrogen or methyl; more preferably, R 10 is hydrogen or methyl, and R 11 is methyl, R8 and R9 are independently of one another halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0104] In another preferred group of compounds of formula I-1, R1 is ethyl or cyclopropylmethyl, preferably, R1 is ethyl; X is S or SO2, preferably, X is SO2; R2 and R3 are independently hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; R8 and R9 are independently of one another halogen, trifluoromethyl, 1,1-difluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, or aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, trifluoromethyl, -OCHF2, -OCF3, trifluoromethylsulfanyl, trifluoromethylsulfinyl and trifluoromethylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0105] In all preferred embodiments of compounds of formula I-1 and compounds of formula I-1 mentioned herein, unless otherwise specified, X, R1, R2, R3, R8, R9, R 10 and R 11 is as defined above under Formula I.

[0106] Another preferred embodiment of the compound having formula I-1 is the compound wherein R1 is ethyl; and X is SO2.

[0107] Also preferred are compounds of formula I-1, wherein R2 and R3 are, independently of one another, hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropoxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0108] Also preferred are compounds of formula I-1, wherein R2 is hydrogen and R3 is hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl) or a compound of formula I-1, wherein R3 is hydrogen and R2 is chloro, bromo, iodo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0109] Also preferred are compounds of formula I-1, wherein R2 is hydrogen and R3 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or compounds of formula I-1, wherein R3 is hydrogen and R2 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0110] Further preferred are compounds of formula I-1, wherein R2 is hydrogen and R3 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or compounds of formula I-1, wherein R3 is hydrogen and R2 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0111] Further preferred are compounds of formula I-1, wherein R8 is hydrogen and R9 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or compounds of formula I-1, wherein R9 is hydrogen and R8 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl;

[0112] Or a compound having formula I-1, wherein R8 and R9 together form a group -O-CF2-O-.

[0113] Another preferred group of compounds having formula I is represented by the following: Compounds having formula I-2

[0114]

[0115] Among them, X, R1, R4, R5, R8, R9, R 10 and R11 is an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound as defined above under formula I, or having formula 1-2.

[0116] In a preferred group of compounds of formula I-2, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; X is S or SO2; R4 and R5 are independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, or -N(R 10 )C(=O)R 11 ; and R 10 and R 11 are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl (preferably cyclopropyl); preferably, R 10 and R 11 are independently hydrogen or methyl; more preferably, R 10 is hydrogen or methyl, and R 11 is methyl, R8 and R9 are independently of one another halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0117] In another preferred group of compounds of formula I-2, R1 is ethyl or cyclopropylmethyl, preferably, R1 is ethyl; X is S or SO2, preferably, X is SO2; R4 and R5 are independently hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; R8 and R9 are independently of one another halogen, trifluoromethyl, 1,1-difluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, or aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, trifluoromethyl, -OCHF2, -OCF3, trifluoromethylsulfanyl, trifluoromethylsulfinyl and trifluoromethylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0118] In all preferred embodiments of compounds of formula I-2 and compounds of formula I-1 mentioned herein, unless otherwise specified, X, R1, R4, R5, R8, R9, R 10 and R 11 is as defined above under Formula I.

[0119] Another preferred embodiment of the compound of formula I-2 is the compound wherein R1 is ethyl; and X is SO2.

[0120] Also preferred are compounds of formula I-2, wherein R4 and R5 are, independently of one another, hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropoxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0121] Also preferred are compounds of formula I-2, wherein R4 is hydrogen and R5 is hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl) or a compound of formula I-2, wherein R4 is hydrogen and R5 is chloro, bromo, iodo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0122] Also preferred are compounds of formula I-2, wherein R4 is hydrogen and R5 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3, or -NCH3C(O)CH3; or compounds of formula I-1, wherein R3 is hydrogen and R2 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3, or -NCH3C(O)CH3.

[0123] Further preferred are compounds of formula I-2, wherein R4 is hydrogen and R5 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or compounds of formula I-1, wherein R3 is hydrogen and R2 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0124] Further preferred are compounds of formula I-2, wherein R8 is hydrogen and R9 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or compounds of formula I-2, wherein R9 is hydrogen and R8 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl;

[0125] Or a compound having formula I-2, wherein R8 and R9 together form a group -O-CF2-O-.

[0126] Another preferred group of compounds having formula I is represented by the following: Compounds having formula I-3

[0127]

[0128] Among them, A, A1, A2, X, R1, R6, R7, R8, R9, R 12 and R 13 is an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound as defined above under formula I, or having formula I-3.

[0129] In a preferred group of compounds of formula I-3, A is CH or N; A1 is CH or N; A2 is CH or N; R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; X is S or SO2; R6 and R7 are independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, or -N(R 12 )C(=O)R 13 ; and R 12 and R 13 are independently hydrogen or C1-C4 alkyl; preferably, R 12 and R 13 are independently hydrogen or methyl; more preferably, R 12 is hydrogen or methyl, and R 13R8 and R9 are independently of one another halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0130] In another preferred group of compounds of formula I-3, A is CH or N, preferably, A is N; A1 is CH or N; A2 is CH or N; R1 is ethyl or cyclopropylmethyl, preferably, R1 is ethyl; X is S or SO2, preferably, X is SO2; R6 and R7 are independently hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or - NCH3C(O)CH3; R8 and R9 are independently of one another halogen, trifluoromethyl, 1,1-difluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, trifluoromethyl, -OCHF2, -OCF3, trifluoromethylsulfanyl, trifluoromethylsulfinyl and trifluoromethylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0131] In all preferred embodiments of compounds of formula I-3 and compounds of formula I-3 mentioned herein, unless otherwise specified, A, A1, A2, X, R1, R6, R7, R8, R9, R 12 and R 13 is as defined above under Formula I.

[0132] Another preferred embodiment of the compound of formula I-3 is the compound wherein R1 is ethyl; and X is SO2.

[0133] Also preferred are compounds of formula I-3, wherein R6 and R7 are, independently of one another, hydrogen, chlorine, bromine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropoxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0134] Also preferred are compounds of formula I-3, wherein R6 is hydrogen and R7 is hydrogen, chloro, bromo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl) or a compound of formula I-3, wherein R7 is hydrogen and R6 is chloro, bromo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0135] Also preferred are compounds of formula I-3, wherein R6 is hydrogen and R7 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or

[0136] A compound of formula I-3, wherein R7 is hydrogen and R7 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0137] Further preferred are compounds of formula I-3, wherein R6 is hydrogen and R7 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or

[0138] A compound of formula I-3, wherein R7 is hydrogen and R6 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3.

[0139] Further preferred are compounds of formula I-3, wherein R8 is hydrogen and R9 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or compounds of formula I-3, wherein R9 is hydrogen and R8 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl;

[0140] Or a compound having formula I-3, wherein R8 and R9 together form a group -O-CF2-O-.

[0141] Another group of preferred compounds according to this embodiment are compounds of formula (I-3a), which are compounds of formula I-3, or any preferred embodiment of compounds of formula I-3, wherein A is CH.

[0142] Another group of preferred compounds according to this embodiment are compounds of formula (I-3b), which are compounds of formula I-3, or any preferred embodiment of compounds of formula I-3, wherein A is N.

[0143] Yet another group of preferred compounds according to this embodiment are compounds of formula (I-3c), which are compounds of formula I-3, or any preferred embodiment of compounds of formula I-3, wherein A1 is CH and A2 is N.

[0144] Another group of preferred compounds according to this embodiment are compounds of formula (I-3d), which are compounds of formula I-3, or any preferred embodiment of compounds of formula I-3, wherein A1 is N and A2 is CH.

[0145] Another group of preferred compounds according to this embodiment are compounds of formula (I-3e), which are compounds of formula I-3, or any preferred embodiment of compounds of formula I-3, wherein both A1 and A2 are N.

[0146] Even more preferred are compounds according to this embodiment having formula (I-3f), which are compounds having formula I-3, or any preferred embodiment of compounds having formula I-3, wherein both A1 and A2 are CH.

[0147] Most preferred are compounds according to this embodiment having formula (I-3g), which are compounds having formula I-3, or any preferred embodiment of compounds having formula I-3, wherein A is N and both A1 and A2 are CH.

[0148] Another preferred group of compounds having formula I is represented by the following: Compounds having formula I-4

[0149]

[0150] in

[0151] Q1 is a group selected from the group consisting of formulae Q1a, Q1b, and Q1c,

[0152]

[0153] wherein the arrow indicates the point of attachment to the nitrogen atom of the tricyclic ring;

[0154] And among them A, A1, A2, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 、R 12 and R 13 is an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound as defined above under formula I, or having formula I-4.

[0155] In all preferred embodiments of compounds of formula I-4 and compounds of formula I-4 mentioned herein, unless otherwise specified, A, A1, A2, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 、R 12 and R 13 is as defined above under Formula I.

[0156] A preferred group of compounds of formula I-4 are compounds of formula (I-4a), which are compounds of formula I-4, or any preferred embodiment of compounds of formula I-4, wherein Q is Q1a, R2 is hydrogen and R3 is hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, -N(R 10 R 11 ), or -N(R 10 )C(=O)R 11 ; and R 10 and R 11 are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl (preferably cyclopropyl); or

[0157] wherein Q is Q1a, R3 is hydrogen and R2 is hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, -N(R 10 R 11 ), or -N(R 10 )C(=O)R 11 ; and R 10 and R 11R8 is hydrogen and R9 is halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl which is optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl. -C4 alkylsulfonyl; or R9 is hydrogen and R8 is halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0158] Further preferred are compounds of formula I-4a, wherein R2 is hydrogen and R3 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or compounds of formula I-4a Compounds wherein R3 is hydrogen and R2 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; R8 is hydrogen and R9 is halogen, trifluoromethyl, 1,1-difluoroethyl, trifluoromethyl R9 is hydrogen and R8 is halogen, trifluoromethyl, 1,1-difluoroethyl, 1,2 ... , trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, trifluoromethyl, -OCHF2, -OCF3, trifluoromethylsulfanyl, trifluoromethylsulfinyl and trifluoromethylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0159] Also preferred are compounds of formula I-4a, wherein R2 and R3 are, independently of one another, hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropoxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0160] Also preferred are compounds of formula I-4a, wherein R2 is hydrogen and R3 is hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl) or a compound of formula I-4a, wherein R3 is hydrogen and R2 is chloro, bromo, iodo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0161] Further preferred are compounds of formula I-4a, wherein R8 is hydrogen and R9 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or compounds of formula I-4a, wherein R9 is hydrogen and R8 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or compounds of formula I-4a, wherein R8 and R9 together form a group -O-CF2-O-.

[0162] Another preferred group of compounds of formula I-4 are compounds of formula (I-4b), which are compounds of formula I-4, or any preferred embodiment of compounds of formula I-4, wherein Q is Qlb, R4 is hydrogen and R5 is hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, -N(R 10 R 11 ), or -N(R 10 )C(=O)R 11 ; and R 10 and R 11 are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl (preferably cyclopropyl); or

[0163] wherein Q is Q1b, R5 is hydrogen and R4 is hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, -N(R 10 R 11 ), or -N(R 10 )C(=O)R 11 ; R 10 and R 11 R8 is hydrogen and R9 is halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl which is optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl. -C4 alkylsulfonyl; or R9 is hydrogen and R8 is halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0164] Further preferred are compounds of formula I-4b, wherein R6 is hydrogen and R5 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or compounds of formula I-4b Compounds wherein R5 is hydrogen and R6 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; R8 is hydrogen and R9 is halogen, trifluoromethyl, 1,1-difluoroethyl, trifluoromethyl R9 is hydrogen and R8 is halogen, trifluoromethyl, 1,1-difluoroethyl, 1,2 ... , trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, trifluoromethyl, -OCHF2, -OCF3, trifluoromethylsulfanyl, trifluoromethylsulfinyl and trifluoromethylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0165] Also preferred are compounds of formula I-4b, wherein R4 and R5 are, independently of one another, hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropoxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0166] Also preferred are compounds of formula I-4b, wherein R4 is hydrogen and R5 is hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl) or a compound of formula I-4b, wherein R5 is hydrogen and R4 is chloro, bromo, iodo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0167] Further preferred are compounds of formula I-4b, wherein R8 is hydrogen and R9 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or compounds of formula I-4b, wherein R9 is hydrogen and R8 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or compounds of formula I-4b, wherein R8 and R9 together form a group -O-CF2-O-.

[0168] Another preferred group of compounds of formula I-4 are compounds of formula (I-4c), which are compounds of formula I-4, or any preferred embodiment of compounds of formula I-4, wherein Q is Q1c, R6 is hydrogen and R7 is hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy or -N(R 12 )C(=O)R 13 ; and R 12 and R 13 are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl; or

[0169] wherein Q is Q1c, R7 is hydrogen and R7 is hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy or -N(R 12 )C(=O)R 13 ; and R 12 and R 13 R8 is hydrogen and R9 is halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl which is optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl. -C4 alkylsulfonyl; or R9 is hydrogen and R8 is halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0170] Further preferred are compounds of formula I-4c, wherein R6 is hydrogen and R7 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3 or -NCH3C(O)CH3; or

[0171] A compound of formula I-4c wherein R7 is hydrogen and R8 is trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, trifluoromethoxy, -CHF2, -OC(CH3)2CN, -NHC(O)CH3, or -NCH3C(O)CH3; R8 is hydrogen and R9 is halogen, trifluoromethyl, 1,1-difluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, or optionally 1 to 3 independently selected from the group consisting of or R9 is hydrogen and R8 is halogen, trifluoromethyl, 1,1-difluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, -OCHF2, -OCH2CHF2, -OCH2CF3, cyclopropyl, or aryl optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, trifluoromethyl, -OCHF2, -OCF3, trifluoromethylsulfanyl, trifluoromethylsulfinyl and trifluoromethylsulfonyl; or R8 and R9 together form a group -O-CF2-O-.

[0172] Also preferred are compounds of formula I-4c, wherein R6 and R7 are, independently of one another, hydrogen, chlorine, bromine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropoxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0173] Also preferred are compounds of formula I-4c, wherein R6 is hydrogen and R7 is hydrogen, chloro, bromo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl) or a compound of formula I-4c, wherein R7 is hydrogen and R6 is chloro, bromo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

[0174] Further preferred are compounds of formula I-4c, wherein R8 is hydrogen and R9 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or compounds of formula I-4c, wherein R9 is hydrogen and R8 is halogen (preferably fluorine, chlorine, bromine), trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or compounds of formula I-4c, wherein R8 and R9 together form a group -O-CF2-O-.

[0175] Another group of preferred compounds according to this embodiment are compounds of formula (I-4c-1), which are compounds of formula I-4c, or any preferred embodiment of compounds of formula I-4c, wherein A is CH.

[0176] Another group of preferred compounds according to this embodiment are compounds of formula (I-4c-2), which are compounds of formula I-4c, or any preferred embodiment of compounds of formula I-4c, wherein A is N.

[0177] Yet another group of preferred compounds according to this embodiment are compounds of formula (I-4c-3), which are compounds of formula I-4c, or any preferred embodiment of compounds of formula I-4c, wherein A1 is CH and A2 is N.

[0178] Another group of preferred compounds according to this embodiment are compounds of formula (I-4c-4), which are compounds of formula I-4c, or any preferred embodiment of compounds of formula I-4c, wherein A1 is N and A2 is CH.

[0179] Another group of preferred compounds according to this embodiment are compounds of formula (I-4c-5), which are compounds of formula I-4c, or any preferred embodiment of compounds of formula I-4c, wherein both A1 and A2 are N.

[0180] Another group of preferred compounds according to this embodiment are compounds of formula (I-4c-6), which are compounds of formula I-4c, or any preferred embodiment of compounds of formula I-4c, wherein both A1 and A2 are CH.

[0181] Another group of preferred compounds according to this embodiment are compounds of formula (I-4c-7), which are compounds of formula I-4c, or any preferred embodiment of compounds of formula I-4c, wherein A is N and both A1 and A2 are CH.

[0182] The compounds according to the present invention may have any number of benefits, including, among others, favorable levels of biological activity for protecting plants against insects or superior properties for use as agrochemical active ingredients (e.g., higher biological activity, favorable activity spectrum, increased safety profile, improved physico-chemical properties, or increased biodegradability or environmental profile). In particular, it has been unexpectedly discovered that certain compounds of formula (I) may exhibit favorable safety profiles relative to non-target arthropods, particularly pollinators (such as honey bees, solitary bees, and bumblebees). Most particularly, relative to the Italian honey bee (Apis mellifera).

[0183] In another aspect, the present invention provides a composition comprising an insecticidal, acaricidal, nematicidal or molluscicidal effective amount of a compound of formula (I) as defined in any one of the Examples (above) under compounds of formula (I), (I-1), (I-2), (I-3) and (I-4), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, and optionally an adjuvant or diluent.

[0184] In another aspect, the present invention provides a method for combating and controlling insects, acarids, nematodes or molluscs, which method comprises applying to the pest, the locus of the pest, or a plant susceptible to attack by the pest an insecticidally, acaridically, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in any one of the Examples (above) under compounds of formula (I), (I), (I-1), (I-2), (I-3) and (I-4), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, or a composition as defined above.

[0185] In yet another aspect, the present invention provides a method for protecting plant propagation material from attack by insects, acarids, nematodes or molluscs, which method comprises treating the propagation material or the locus in which the propagation material is planted with a composition as defined above.

[0186] The method for preparing the compound of formula I according to the present invention is carried out in principle by methods known to those skilled in the art. More specifically, and as described in schemes 1, 2 and 3, a subgroup of compounds of formula I (wherein X is SO (sulfoxide) and / or SO2 (sulfone)) can be obtained by means of an oxidation reaction of a corresponding sulfide compound of formula I (wherein X is S), the oxidation reaction involving a reagent such as m-chloroperbenzoic acid (mCPBA), hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite or tert-butyl hypochlorite and other oxidants. The oxidation reaction is typically carried out in the presence of a solvent. Examples of solvents for the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; esters such as ethyl acetate; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof. The amount of the oxidant used in this reaction is generally 1 to 3 moles, preferably 1 to 1.2 moles, relative to 1 mole of the sulfide compound I to form the sulfoxide compound I, and preferably 2 to 2.2 moles relative to 1 mole of the sulfide compound I to form the sulfone compound I. Such oxidation reactions are disclosed, for example, in WO 2013 / 018928.

[0187] Solution 1 (All substituents are as defined in Formula I)

[0188]

[0189] The chemical process described above in Scheme 1 to obtain compounds of formula I-a2 and formula I-a3 from compounds of formula I-a1 can be applied analogously (Scheme 2) to prepare compounds of formula I-a5 and formula I-a6 from compounds of formula I-a4, wherein all previously mentioned substituent definitions remain valid.

[0190] Option 2(All substituents are as defined in Formula I)

[0191]

[0192] The chemical process described above in Scheme 1 to obtain compounds of formula I-a2 and formula I-a3 from compounds of formula I-a1 can be applied analogously (Scheme 3) to prepare compounds of formula I-a8 and formula I-a9 from compounds of formula I-a7, wherein all previously mentioned substituent definitions remain valid.

[0193] Option 3 (All substituents are as defined in Formula I)

[0194]

[0195] A subset of compounds having Formula I (wherein R8 and R9 are as defined in Formula I and wherein Q is defined as Qa, wherein R1, R2, R3 and X are as defined in Formula I) can be defined as compounds having Formula I-1.

[0196] Option 4

[0197]

[0198] Such compounds of formula I-1 can be prepared by a Suzuki cross-coupling reaction (Scheme 4), which involves, for example, reacting a compound of formula II-1 (wherein R1, R2, R3 and X are as defined in formula I, and wherein Xa is a leaving group such as, for example, chloro, bromo or iodo, or an aryl sulfonate or alkyl sulfonate such as trifluoromethanesulfonate) with a compound of formula III (wherein R8 and R9 are as defined in formula I, and wherein Ya is a boron-derived functional group such as, for example, B(OH)2 or B(OR b1 )2, where R b1 It can be C1-C4 alkyl or these two groups OR b1The reaction can be carried out by a palladium-based catalyst (e.g., tetrakis(triphenylphosphine)palladium or (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium-dichloromethane (1:1 complex)) in the presence of a base (e.g., sodium carbonate, potassium carbonate, or cesium fluoride) in a solvent or solvent mixture (e.g., a mixture of 1,2-dimethoxyethane and water, a mixture of dioxane and water, or a mixture of acetonitrile and water), preferably under an inert atmosphere. The reaction temperature can preferably range from ambient temperature to the boiling point of the reaction mixture. This type of Suzuki reaction is well known to those skilled in the art and has been reviewed, for example, in J.Orgmet.Chem. [Journal of Organometallic Chemistry] 576, 1999, 147-168.

[0199] Alternatively, compounds of formula I-1 can be prepared by a Stirler cross-coupling reaction of a compound of formula III (wherein Ya is a trialkyltin derivative, preferably tri-n-butyltin) with a compound of formula II-2 (wherein Xa is a leaving group, such as, for example, chlorine, bromine or iodine, or an arylsulfonate or alkylsulfonate, such as trifluoromethanesulfonate). Such Stirler reactions are typically carried out in the presence of a palladium catalyst (e.g., tetrakis(triphenylphosphine)-palladium(0), or (1,1'bis(diphenylphosphino)-ferrocene)dichloropalladium-dichloromethane (1:1 complex)) in an inert solvent (e.g., DMF, acetonitrile, or dioxane), optionally in the presence of an additive (e.g., cesium fluoride or lithium chloride), and optionally in the presence of an additional catalyst (e.g., copper(I) iodide). Such Stiller couplings are also familiar to those skilled in the art and have been described, for example, in J. Org. Chem., 2005, 70, 8601-8604, J. Org. Chem., 2009, 74, 5599-5602, and Angew. Chem. Int. Ed., 2004, 43, 1132-1136.

[0200] A subset of compounds having Formula I (wherein R8 and R9 are as defined in Formula I and wherein Q is defined as Qb, wherein R1, R4, R5 and X are as defined in Formula I) can be defined as compounds having Formula I-2.

[0201] Option 5

[0202]

[0203] The chemical process previously described in Scheme 4 for obtaining compounds of formula I-1 from compounds of formula III and compounds of formula II-1 can be applied analogously to the preparation of compounds of formula I-2 from compounds of formula III and compounds of formula II-2 (Scheme 5), wherein all substituent definitions mentioned previously remain valid.

[0204] A subset of compounds having Formula I (wherein R8 and R9 are as defined in Formula I and wherein Q is defined as Qc, wherein R1, R6, R7, A, A1, A2 and X are as defined in Formula I) can be defined as compounds having Formula I-3.

[0205] Option 6

[0206]

[0207] The chemical process previously described in Scheme 4 for obtaining a compound of formula I-1 from a compound of formula III and a compound of formula II-1 can be applied analogously to the preparation of a compound of formula I-3 from a compound of formula III and a compound of formula II-3 (Scheme 6), wherein all substituent definitions mentioned previously remain valid.

[0208] Compounds of formula III (wherein R8 and R9 are as defined in formula I, and wherein Ya is a boron-derived functional group such as, for example, B(OH)2 or B(OR b1 )2, where R b1 It can be C1-C4 alkyl or these two groups OR b1 can form a five-membered ring together with a boron atom, such as pinacol borate),

[0209] Option 7

[0210]

[0211] It can be prepared by reacting a compound of formula IV wherein R8 and R9 are as defined in formula I and wherein Xb is a leaving group such as, for example, chloro, bromo or iodo under the borylation conditions detailed in Scheme 8 (Scheme 7).

[0212] Alternatively, compounds of formula III, wherein R8 and R9 are as defined in formula I, and wherein Ya is a trialkyltin derivative, preferably tri-n-butyltin, can be prepared via a stannylation step involving, for example, reacting a compound of formula IV with an organometallic species, such as, for example, an organomagnesium compound (e.g., isopropylmagnesium chloride), to produce an intermediate species via a metal-halogen exchange, preferably carried out in an anhydrous aprotic solvent such as tetrahydrofuran at low temperatures, preferably between -78°C and 0°C, and quenching the intermediate species with a tin reagent of formula (alkyl)3SnCl, such as tri-n-butyltin chloride (n-butyl)3SnCl.

[0213] Similarly, compounds of formula IIIa (a subset of compounds of formula III) wherein R8 and R9 are as defined in formula I, and wherein Ya is B(OR b1 )2, where R b1 is a C1-C4 alkyl group),

[0214] Option 8

[0215]

[0216] The intermediate species may be produced by reacting a compound of formula IV wherein R8 and R9 are as defined in formula I and wherein Xb is a leaving group such as, for example, chlorine, bromine or iodine with an organometallic species such as, for example, an organomagnesium compound such as isopropylmagnesium chloride or isopropylmagnesium chloride lithium chloride complex to produce an intermediate species via a metal-halogen exchange, preferably in an anhydrous aprotic solvent such as tetrahydrofuran at low temperatures, preferably between -78°C and 0°C, and reacting the intermediate species with a compound of formula B (OR b1 )3 trialkyl borate reagent (wherein R b1 is C1-C4 alkyl) (Scheme 8). Depending on the nature of the trialkyl borate, the reaction process conditions and the post-processing conditions, dialkyl borate IIIa can be formed and isolated, or boronic acid compounds of formula IIIc (another subgroup of compounds of formula III) can be directly obtained (wherein R8 and R9 are as defined in formula I). ​​Such conditions have been described in the literature, for example, in WO 2017 / 122722.

[0217] Compounds of formula IIIb (yet another subgroup of compounds of formula III) wherein R8 and R9 are as defined in formula I, and wherein Ya is a pinacol borate (also known as a Bpin group, i.e. wherein the two groups OR b1Compounds of formula IV (wherein R and R are as defined in formula I and X is a leaving group such as, for example, chlorine, bromine or iodine) can be prepared by reacting bis(pinacolato)diborane of formula V under palladium-catalyzed reaction conditions. Typically, such conditions involve 1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (optionally as a dichloromethane adduct) in the presence of a base such as potassium acetate or potassium carbonate in an inert solvent such as dioxane, N,N-dimethylformamide or acetonitrile, preferably under an inert atmosphere, at a temperature preferably ranging from ambient temperature to the boiling point of the reaction mixture. Such conditions have been described in the literature, for example in Bioorg. Med. Chem. 15, 7138-7143 (2007). Depending on the reaction process conditions and post-processing conditions, pinacol boronate IIIb will be formed in situ, and the boronic acid compound of formula IIIc can be directly obtained. Such conditions have been described in the literature, for example, in Chem. Pharm. Bull. [Chemistry and Pharmaceutical Bulletin] 68 (8): 797-801 (2020).

[0218] The hydrolysis of the compound of formula IIIa or IIIb to the compound of formula IIIc (all substituents are as defined above) can be carried out by methods known to those skilled in the art, for example with water, optionally in the presence of a co-solvent such as pentane, tetrahydrofuran or methanol, optionally in the presence of an aqueous acid such as hydrochloric acid or an aqueous base such as lithium hydroxide, sodium hydroxide or potassium hydroxide, preferably at a temperature between 0°C and 40°C, even more preferably at a temperature of about 10°C to 30°C.

[0219] A compound of formula IV (wherein R8 and R9 are as defined in formula I and wherein Xb is a leaving group such as, for example, chloro, bromo or iodo),

[0220] Option 9

[0221]

[0222] The compound of formula VI (wherein R8 and R9 are as defined in formula I) can be reacted with an electrophilic halogen source Xb + Reagents (such as bromine Br2, N-bromosuccinimide NBS, iodine I2 or tert-butyl hypochlorite tBuOCl, etc.) (wherein Xb is chlorine, bromine or iodine) are reacted in an inert solvent (such as dichloromethane, chloroform, acetonitrile, dimethylacetamide, methanol, ethanol or pyridine) at a temperature between 0°C and 50°C to prepare (Scheme 9).

[0223] Compounds of formula VI (wherein R8 and R9 are as defined in formula I) can be prepared by reacting compounds of formula VII (wherein R8 and R9 are as defined in formula I) with a reagent of formula VIII under heating conditions, optionally in the presence of a diluent such as N,N-dimethylformamide, dimethylacetamide, toluene or xylene, at a temperature between 50° C. and 180° C., preferably at a temperature ranging from 80° C. to the boiling point of the reaction mixture. The reagent of formula VIII is commercially available N,N-dimethyl-formamide dimethyl acetal DMF-DMA. Such conditions (for both steps in Scheme 7) have been described in the literature, for example in Synthesis 901-903 (1979), Bioorg. Med. Chem. Lett. 25, 2510-2513 (2015) or Eur. J. Org. Chem. 6440-6446 (2020).

[0224] Alternatively, a compound of formula IV (wherein R8 and R9 are as defined in formula I and wherein Xb is a leaving group such as, for example, chloro, bromo or iodo),

[0225] Plan 10

[0226]

[0227] It can be prepared by halogenation of a compound of formula IX (wherein R8 and R9 are as defined in formula I) (Scheme 10). Suitable conditions may involve reacting a compound of formula IX with pyrrolidine or piperidine in an alcohol (such as methanol or ethanol) at a temperature between 30°C and 100°C, preferably at a temperature ranging from 60°C to the boiling point of the reaction mixture, to form an enaminoketone intermediate. Subsequent treatment of the enaminoketone intermediate with a halogenating agent of formula (Xb)2 (wherein Xb is chlorine, bromine or iodine) in an inert solvent (such as chloroform) at a temperature between 0°C and 40°C can provide a compound of formula IV, as described in Synthesis 719-7821 (1981) or Synthesis 901-903 (1979). Alternatively, oxidative halogenation conditions may also be suitable for forming compounds of formula IV, for example by reacting a compound of formula IX with a hydrohalic acid HXb (wherein Xb is chlorine, bromine or iodine) in the presence of oxone (Synthesis (2004), 2641-2644; preferably, Xb is chlorine or bromine) or m-chloroperbenzoic acid (Synthesis (1993), 283-4; preferably, Xb is chlorine) as an oxidant in an inert solvent such as, for example, dichloromethane or N,N-dimethylformamide at a temperature between 0°C and 40°C. Other oxidative halogenation conditions can involve cerium ammonium nitrate (CAN) and iodine (Xb is iodine) in an inert solvent (such as, for example, acetonitrile) at temperatures between 50°C and 90°C, as described in Tetrahedron Letters 72 (2021) article 153070 (https: / / doi.org / 10.1016 / j.tetlet.2021.153070).

[0228] Compounds of formula IX, wherein R and R are as defined in formula I, can be prepared by cyclizing compounds of formula X, wherein R and R are as defined in formula I, and wherein R is hydrogen or C1-C4 alkyl, in the presence of an acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, p-toluenesulfonic acid or polyphosphoric acid, in an inert solvent such as acetic acid, methanol, ethanol, dimethyl sulfoxide or water (or mixtures thereof), at temperatures between 0° C. and 100° C., preferably between room temperature and 80° C. Such conditions have been described in the literature, for example in J. Med. Chem. 33, 1859-1865 (1990). In the specific case where Ra is C1-C4 alkyl, cyclization can be achieved by using potassium carbonate (optionally in catalytic amounts) in an inert solvent such as N,N-dimethylformamide or dimethylacetamide at temperatures between 80°C and 180°C as described in Organic Letters 14, 2710-2713 (2012).

[0229] A compound of formula X (wherein R8 and R9 are as defined in formula I and wherein Ra is hydrogen or C1-C4 alkyl),

[0230] Plan 11

[0231]

[0232] Can be typically prepared from starting materials of formula VII-1 or XI by Claisen condensation type chemistry under conditions known to those skilled in the art (Scheme 11). For example, a compound of formula X can be prepared by a compound of formula VII-1 (wherein R8 and R9 are as defined in formula I, and wherein R a is hydrogen or C1-C4 alkyl) and has the formula HC(O)OR b Reagents (where R b The compounds of formula VII described above (Scheme 9) form a specific subgroup of compounds of formula VII-1 (wherein R a is hydrogen).

[0233] Alternatively, the compound of formula XIII may be prepared by reacting the compound of formula XI (wherein R8 and R9 are as defined in formula I, and wherein R a is hydrogen or C1-C4 alkyl, and R cis chlorine or C1-C4 alkoxy (preferably methoxy or ethoxy)) with a reagent having the formula HC(O)CH3 or a reagent having the formula HC(O)CH2C(O)R d Reagents (where R d is obtained by condensation of a methyl or C1-C4 alkoxy group (preferably a methoxy or ethoxy group) under similar conditions as described above or as adequately selected by a person skilled in the art. Such conditions have been described in the literature, for example in J. Med. Chem. 33, 1859-1865 (1990).

[0234] A compound of formula VII-1 (wherein R8 and R9 are as defined in formula I, and wherein R a is hydrogen or C1-C4 alkyl) (including compounds of formula VII, wherein R8 and R9 are as defined in formula I); and

[0235] A compound of formula XI (wherein R8 and R9 are as defined in formula I, and wherein R a is hydrogen or C1-C4 alkyl, and R c is chlorine or C1-C4 alkoxy (preferably methoxy or ethoxy)

[0236] are known, commercially available or can be prepared by methods known to those skilled in the art.

[0237] A compound of formula II-1 (wherein R1, R2, R3 and X are as defined in formula I, and wherein X a is a leaving group, like for example chlorine, bromine or iodine),

[0238] Plan 12

[0239]

[0240] The preparation of the present invention can be carried out by reacting a compound of formula XII (wherein R1, R2, R3 and X are as defined in formula I) with a nitrite such as tert-butyl nitrite t-BuONO or isoamyl nitrite (an example of non-aqueous conditions) or a hydrohalic acid HXa of sodium nitrite in water (aqueous conditions) and a copper salt Cu(I)Xa (wherein X a is a leaving group such as, for example, chlorine, bromine or iodine) under Sandmeyer-type reaction conditions (Scheme 12). This transformation is preferably carried out in an inert solvent such as acetonitrile or a halogenated solvent such as 1,2-dichloroethane or 1,2-dibromoethane (non-aqueous conditions), or water at a temperature between 0°C and 150°C, preferably at a temperature ranging from room temperature to the boiling point of the reaction mixture.

[0241] A compound of formula II-1 (wherein X is S, and wherein R1, R2 and R3 are as defined in formula I, and wherein X a The oxidation of the compound (wherein X is SO or SO2) to a compound of formula II-1 (wherein X is a leaving group such as, for example, chlorine, bromine or iodine) with a suitable oxidizing agent can be achieved under the conditions already described above.

[0242] The compound of formula XII (wherein R1, R2, R3 and X are as defined in formula I) can be obtained by subjecting the compound of formula XIII (wherein R1, R2, R3 and X are as defined in formula I) to a deprotection reaction (BOC group removal). The reaction can be carried out in the presence of an acid (such as trifluoroacetic acid, hydrochloric acid or sulfuric acid, etc.) and optionally in the presence of a solvent (such as dichloromethane, toluene, trifluorotoluene, etc.).

[0243] A compound of formula XIII (wherein R1, R2, R3 and X are as defined in formula I),

[0244] Plan 13

[0245]

[0246] Can be prepared by reacting a compound of formula XIV (wherein R1, R2, R3 and X are as defined in formula I) with an organic azide in the presence of a suitable base and t-butyl alcohol t-BuOH and in the presence of a coupling agent, optionally in the presence of a Lewis acid and in the presence of an inert solvent at a temperature between 50°C and the boiling point of the reaction mixture (Scheme 13). The reaction can be carried out in the presence of a coupling agent such as T3P. Examples of organic azides include TMSN3, sodium azide, or tosyl azide, and suitable solvents can be toluene, xylene, THF or acetonitrile. Examples of suitable Lewis acids can include Zn(OTf)2, Sc(OTf)2 or Cu(OTf)2 and the like.

[0247] The compound of formula XIII can also be prepared by reacting a compound of formula XIV with diphenylphosphoryl azide in the presence of an organic base (such as triethylamine or diisopropylethylamine, etc.), in the presence of tert-butyl alcohol t-BuOH, in an inert solvent (e.g., a halogenated solvent (such as dichloromethane or dichloroethane) or a cyclic ether (such as tetrahydrofuran, etc.)), and at a temperature ranging from 50° C. to the boiling point of the reaction mixture. Such reactions for converting carboxylic acids into BOC-protected amines are known to those skilled in the art under the name Curtius reaction and are reported, for example, in Org. Lett., 2005, 7, 4107-4110; Journal of Medicinal Chemistry, 49(12), 3614-3627; 2006, J. Am. Chem. Soc., 1972, 94(17), pp. 6203-6205.

[0248] Oxidation of a compound of formula XIV (wherein X is S, and wherein R1, R2 and R3 are as defined in formula I) to a compound of formula XIV (wherein X is SO or SO2) with a suitable oxidizing agent can be achieved under the conditions already described above.

[0249] Compounds of formula XIII (wherein R1, R2, R3 and X are as defined in formula I) can also be prepared from compounds of formula XV (wherein R1, R2, R3 and X are as defined in formula I) by Hofmann rearrangement reaction. The reaction can be carried out in the presence of a base (e.g., a metal hydroxide such as aqueous sodium hydroxide or potassium hydroxide, or an organic base such as DBU (1,8-diazabicyclo(5.4.0)undec-7-ene)), in the presence of an electrophilic halogenating agent such as chlorine, bromine or N-bromosuccinimide, and at a temperature ranging from 20°C to the boiling point of the reaction mixture. This type of reaction is known by the name Hofmann rearrangement and is reported in the literature, for example, in Chem. Ber. [Chemical Reports] 1881, 14, 2725.

[0250] Compounds of formula XV (wherein R1, R2, R3 and X are as defined in formula I) can be prepared by reacting compounds of formula XIV (wherein R1, R2, R3 and X are as defined above in formula I) with ammonia NH3 or other ammonia substitutes (e.g., NH4OH) in the presence of a carboxylic acid activator.

[0251] Oxidation of a compound of formula XV (wherein X is S, and wherein R1, R2 and R3 are as defined in formula I) to a compound of formula XV (wherein X is SO or SO2) with a suitable oxidizing agent can be achieved under the conditions already described above.

[0252] Compounds of formula XIV (wherein R1, R2, R3 and X are as defined in formula I) can be prepared by hydrolysis of compounds of formula XVI (wherein R1, R2, R3 and X are as defined in formula I) with a base (e.g., sodium hydroxide or sodium carbonate) in water, methyl-tetrahydrofuran, methanol, ethanol or a mixture thereof. e is C1-C6 alkyl, benzyl or phenyl, preferably methyl, ethyl or propyl).

[0253] A compound of formula XVI (wherein X is S, and wherein R1, R2 and R3 are as defined in formula I and R e The oxidation of a compound having the formula XVI (wherein X is SO or SO2) to a compound having the formula XVI (wherein X is SO or SO2) can be achieved under the conditions already described above.

[0254] Compounds of Formula XVI (wherein R1, R2 and R3 are as defined in Formula I, X is S and R e is C1-C6 alkyl, benzyl or phenyl, preferably methyl, ethyl, propyl) are known in the literature or they can be prepared by following Scheme 14 using analogous methods and conditions as described, for example, in WO / 2017 / 061497 and WO / 2018 / 052136.

[0255] Option 14:

[0256]

[0257] A compound of formula II-2 (wherein R1, R4, R5 and X are as defined in formula I, and wherein X a is a leaving group, like for example chlorine, bromine or iodine),

[0258] Plan 15

[0259]

[0260] It can be prepared by reacting a compound of formula XXI, wherein R1, R4, R5 and X are as defined in formula I, under Sandmeyer conditions as described above for Scheme 12 (Scheme 15).

[0261] A compound of formula II-2 (wherein X is S, and wherein R1, R4 and R5 are as defined in formula I, and wherein X is a The oxidation of a compound having the formula II-2 (wherein X is SO or SO2) to a compound having the formula II-2 (wherein X is a leaving group, such as for example chlorine, bromine or iodine) can be achieved under the conditions already described above.

[0262] Compounds of formula XXI (wherein R1, R4, R5 and X are as defined in formula I) can be obtained by subjecting compounds of formula XXII (wherein R1, R4, R5 and X are as defined in formula I) to a deprotection reaction (BOC group removal) as described above for Scheme 12.

[0263] A compound of formula XXII (wherein R1, R4, R5 and X are as defined in formula I),

[0264] Plan 16

[0265]

[0266] It can be prepared by reaction of a compound of formula XXIII (wherein R1, R4, R5 and X are as defined in formula I) under Curtius conditions as described above for Scheme 13 (Scheme 16).

[0267] Oxidation of a compound of formula XXIII (wherein X is S, and wherein R1, R4 and R5 are as defined in formula I) to a compound of formula XXIII (wherein X is SO or SO2) with a suitable oxidizing agent can be achieved under the conditions already described above.

[0268] Compounds of formula XXII, wherein R1, R4, R5 and X are as defined in formula I, can also be prepared from compounds of formula XXIV, wherein R1, R4, R5 and X are as defined in formula I, by a Hofmann rearrangement reaction as described above for Scheme 13.

[0269] Compounds of formula XXIV (wherein R1, R4, R5 and X are as defined in formula I) can be prepared by reacting compounds of formula XXIII (wherein R1, R4, R5 and X are as defined above in formula I) with ammonia NH3 or other ammonia substitutes (e.g., NH4OH) in the presence of a carboxylic acid activator.

[0270] Oxidation of a compound of formula XXIV (wherein X is S, and wherein R1, R4 and R5 are as defined in formula I) to a compound of formula XXIV (wherein X is SO or SO2) with a suitable oxidizing agent can be achieved under the conditions already described above.

[0271] Compounds of formula XXIII (wherein R1, R4, R5 and X are as defined in formula I) can be prepared by hydrolysis of compounds of formula XXV (wherein R1, R4, R5 and X are as defined in formula I) with a base (e.g., sodium hydroxide or sodium carbonate) in water, methyl-tetrahydrofuran, methanol, ethanol or a mixture thereof.f is C1-C6 alkyl, benzyl or phenyl, preferably methyl, ethyl or propyl).

[0272] A compound of formula XXV (wherein X is S, and wherein R1, R4 and R5 are as defined in formula I and R f The oxidation of a compound having the formula XXV (wherein X is SO or SO2) to a compound having the formula XXV (wherein X is SO or SO2) can be achieved under the conditions already described above.

[0273] Compounds of formula XXV (wherein R1, R4 and R6 are as defined in formula I, X is S and R f is C1-C6 alkyl, benzyl or phenyl, preferably methyl, ethyl, propyl) are known in the literature or they can be prepared by following Scheme 17 using analogous methods and conditions as described, for example, in WO / 2019 / 162174.

[0274] Option 17:

[0275]

[0276] A compound of formula II-3 (wherein R1, R6, R7, A, A1, A2 and X are as defined in formula I, and wherein X a is a leaving group, like for example chlorine, bromine or iodine),

[0277] Plan 18

[0278]

[0279] Can be prepared by reacting a compound of formula XXXI wherein R1, R6, R7, A, A1, A2 and X are as defined in formula I under Sandmeyer conditions as described above for Scheme 12 (Scheme 18).

[0280] A compound of formula II-3 (wherein X is S, and wherein R1, R6, R7, A, A1 and A2 are as defined in formula I, and wherein X is a The oxidation of 2-H-oxo-1-oxo-2-oxo-2-oxo-2-oxo-3-oxo-4-oxo-2 ...

[0281] Compounds of formula XXXI, wherein R1, R6, R7, A, Al, A2 and X are as defined in formula I, can be obtained by subjecting compounds of formula XXXII, wherein R1, R6, R7, A, Al, A2 and X are as defined in formula I, to deprotection reaction (BOC group removal) as described above for Scheme 12.

[0282] A compound of formula XXXII (wherein R1, R6, R7, A, A1, A2 and X are as defined in formula I),

[0283] Plan 19

[0284]

[0285] It can be prepared by reacting a compound of formula XXXIII (wherein R1, R6, R7, A, A1, A2 and X are as defined in formula I) under Curtius conditions as described above for Scheme 13 (Scheme 19).

[0286] Oxidation of a compound of formula XXXIII (wherein X is S, and wherein R1, R6, R7, A, A1, A2 and X are as defined in formula I) to a compound of formula XXXIII (wherein X is SO or SO2) with a suitable oxidizing agent can be achieved under the conditions already described above.

[0287] Compounds of formula XXXII, wherein R1, R6, R7, A, Al, A2, and X are as defined in formula I, can also be prepared from compounds of formula XXXIV, wherein R1, R6, R7, A, Al, A2, and X are as defined in formula I, by a Hofmann rearrangement reaction as described above for Scheme 13.

[0288] Compounds of formula XXXIV, wherein R1, R6, R7, A, A1, A2, and X are as defined in formula I, can be prepared by reacting compounds of formula XXXIII, wherein R1, R6, R7, A, A1, A2, and X are as defined above in formula I, with ammonia NH3 or other ammonia substitutes (e.g., NH4OH) in the presence of a carboxylic acid activator.

[0289] Oxidation of a compound of formula XXXIV (wherein X is S, and wherein R1, R6, R7, A, A1 and A2 are as defined in formula I) to a compound of formula XXXIV (wherein X is SO or SO2 and wherein R1, R6, R7, A, A1 and A2) with a suitable oxidizing agent can be achieved under the conditions already described above.

[0290] Compounds of formula XXXIII (wherein R1, R6, R7, A, A1, A2 and X are as defined in formula I) can be prepared by hydrolysis of compounds of formula XXXV (wherein R1, R6, R7, A, A1, A2 and X are as defined in formula I) with a base (e.g., sodium hydroxide or sodium carbonate) in water, methyl-tetrahydrofuran, methanol, ethanol or a mixture thereof. g is C1-C6 alkyl, benzyl or phenyl, preferably methyl, ethyl or propyl).

[0291] A compound of formula XXXV (wherein X is S, and wherein R1, R6, R7, A, A1 and A2 are as defined in formula I and R g The oxidation of a compound having the formula XXXV (wherein X is SO or SO2 and wherein R1, R6, R7, A, A1 and A2) to a compound having the formula XXXV can be achieved under the conditions already described above.

[0292] Compounds of formula XXXV are known in the literature or they can be prepared by following analogous methods as described in, for example, WO / 2016 / 142326 and WO / 2016 / 091731.

[0293] A subset of compounds having formula II-3a, wherein R1, R6, R7, A1, A2 and X are as defined in formula I, A is N and Xa is chloro or bromo, can be prepared following Scheme 20.

[0294] Plan 20

[0295]

[0296] Compounds of formula II-3a (wherein R1, R6, R7, A1 and A2 are as defined in formula I and wherein X is S and Xa is halogen, preferably bromine or chlorine) can be prepared by reacting a compound of formula XXXVI (wherein R1, R6, R7, A1 and A2 are as defined in formula I and wherein X is S) with a halogenating agent (such as POCl3 or POBr3 or trichloroacetonitrile) in the presence of triphenylphosphine or other halogenating agents capable of converting heteroaryl N-oxides into halogen-functionalized derivatives. Such reactions are well known in the literature and are described, for example, in Tetrahedron Letters (2014), 55(51), 7130-7132, Tetrahedron (2005), 61(38), 9042-9051 and European Journal of Organic Chemistry (2016), 2016(8), 1606-1611.

[0297] Compounds of formula XXXVI (wherein R1, R6, R7, A1 and A2 are as defined in formula I and wherein X is S) can be prepared by reacting compounds of formula XXXVII (wherein R1, R6, R7, A1 and A2 are as defined in formula I and wherein X is S) with an oxidizing agent (such as urea-H2O2, m-CPBA and other oxidizing agents) in the presence of a solvent (such as acetonitrile, tetrahydrofuran, dichloromethane, dichloroethane, etc.). Such reactions are well known in the literature and are described, for example, in Organic Letters (2018), 20(8), 2346-2350, Dalton Transactions (2014), 43(21), 8054-8061 and Chemische Berichte (1992), 125(8), 1965-6.

[0298] Compounds of formula XXXXVII, wherein R1, R6, R7, A1, and A2 are as defined in formula I and wherein X is S, can be prepared from compounds of formula XXXXVIII, wherein R1, R6, R7, A1, and A2 are as defined in formula I and wherein X is S. c is a halogen (or a pseudohalogen leaving group such as triflate)) by substitution reaction or by reacting the compound with a reagent having formula XXXIXa

[0299] R1-SH(XXXIXa),

[0300] or a salt thereof (wherein R1 is as defined in formula I) is optionally prepared by a cross-coupling reaction in the presence of a suitable base (such as an alkali metal carbonate, for example sodium carbonate and potassium carbonate, or an alkali metal hydride such as sodium hydride, or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide, or sodium tert-butoxide or potassium tert-butoxide) in an inert solvent at a temperature preferably between 25°C and 120°C. Examples of solvents to be used include ethers such as tetrahydrofuran THF, ethylene glycol dimethyl ether, tert-butyl methyl ether and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; or polar aprotic solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone NMP or dimethyl sulfoxide. Examples of salts of compounds of formula XXXIXa include compounds of the formula

[0301] R1-SM(XXXIXb),

[0302] wherein R1 is as defined above and wherein M is, for example, sodium or potassium. Such a process for preparing compounds of formula XXXXb from compounds of formula XXXXa can be found, for example, in WO / 2016 / 091731.

[0303] Alternatively, this reaction of forming a compound of formula XXXVII from a compound of formula XXXVIII using R1-SH(XXXIXa) or R1-SM(XXXIXb) can be carried out in the presence of a palladium catalyst such as tris(dibenzylideneacetone)dipalladium(0) in the presence of a phosphine ligand such as xanthphos, in the presence of a base such as N,N-diisopropylethylamine, and in the presence of an inert solvent such as xylene at a temperature between 100°C and 160°C (preferably 140°C) as described in Tetrahedron 2005, 61, 5253-5259.

[0304] Alternatively, a compound of formula I (wherein R8, R9 and Q are as defined in formula I)

[0305] Plan 21

[0306]

[0307] Can be prepared by cyclizing a compound of formula XXXX (wherein Q (in this Scheme 21, the arrow in Qa (respectively Qb and Qc) indicates the point of attachment to the ortho-carbon atom of the carbonyl group), R8 and R9 are as defined in formula I and wherein Ra is hydrogen or C1-C4 alkyl) under similar conditions as those described in Scheme 10 for converting a compound of formula X to a compound of formula IX (Scheme 21). Other such cyclization conditions have also been described in the literature, for example in WO / 2007 / 065888 or Eur.J.Org.Chem. [European Journal of Organic Chemistry], (2019), 2971-2983.

[0308] Compounds of formula XXXX wherein Q (in this Scheme 22, the arrows in Qa (respectively Qb and Qc) indicate the point of attachment to the carbon atom adjacent to the carbonyl group), R8 and R9 are as defined in formula I and wherein R a is hydrogen or C1-C4 alkyl),

[0309] Plan 22

[0310]

[0311] The alkyl sulfonate can be prepared by reacting a compound of formula X (wherein R8 and R9 are as defined in formula I and wherein Ra is hydrogen or C1-C4 alkyl) with a compound of formula II-1, II-2 or II-3a (wherein R1, R2, R3, R4, R5, R6, R7, X, A1 and A2 are as defined in formula I and wherein Xa is a leaving group such as, for example, chloro, bromo or iodo, or an aryl sulfonate or an alkyl sulfonate such as trifluoromethanesulfonate) in the presence of a base such as lithium diisopropylamide, potassium bis(trimethylsilyl)amide, Prepared by reacting in the presence of potassium carbonate, sodium methoxide, sodium ethoxide, potassium tert-butoxide or sodium hydride, optionally under copper or palladium catalysis, in an inert solvent such as tetrahydrofuran, tert-butyl ethyl ether or N,N-dimethylformamide and at a temperature between 0°C and 80°C (Scheme 22). Reaction of X with II-1 provides XXXX (wherein Q is Qa); similarly, reaction of X with II-2 provides XXXX (wherein Q is Qb), and reaction of X with II-3a provides XXXX (wherein Q is Qb, where A is N).

[0312] These reactants can react with each other as is, i.e. without adding solvent or diluent. However, in most cases, it is advantageous to add an inert solvent or diluent or a mixture of these. If the reaction is carried out in the presence of a base, the base (such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylaniline) used in excess can also serve as a solvent or diluent.

[0313] These reactions are advantageously carried out in a temperature range of from about -80°C to about +140°C, preferably from about -30°C to about +100°C, in many cases in a range between ambient temperature and about +80°C.

[0314] Alternatively, a compound of formula I (wherein R8, R9 and Q are as defined in formula I),

[0315] Plan 23

[0316]

[0317] Can be prepared by reacting a compound of formula XXXXII (wherein Q (in this Scheme 23, the arrow in Qa (respectively Qb and Qc) indicates the point of attachment to the ortho-carbon atom of the carbonyl group), R8 and R9 are as defined in Formula I) with a reagent of formula XIII under similar conditions already described in Scheme 9 for converting a compound of formula VII into a compound of formula VI (Scheme 23). The reagent of formula VIII is N,N-dimethylformamide dimethyl acetal DMF-DMA. Reacting XXXXII and VIII under such conditions allows the direct formation of a compound of formula I without the need to isolate a possible intermediate compound of formula XXXXI (wherein R8, R9 and Q are as defined in Formula I). ​​Such cyclization conditions have been described in the literature, for example in WO / 2015 / 047113.

[0318] Similarly, a compound of formula I (wherein R8, R9 and Q are as defined in formula I) can be prepared by reacting a compound of formula XXXXII (wherein R8, R9 and Q are as defined in formula I) with a reagent of formula XXXXIV (wherein R h is C1-C4 alkyl) is preferably prepared by reacting in the presence of an additive (optionally in catalytic amounts) such as pyridine, piperidine, morpholine or 4-dimethylaminopyridine (DMAP), optionally in the presence of a diluent such as N,N-dimethylformamide, dimethylacetamide, toluene or xylene at a temperature between 50° C. and 180° C., preferably in a temperature range from 80° C. to the boiling point of the reaction mixture (Scheme 23). Typically, the reagent of formula XXXXIV is, for example, triethyl orthoformate (R h is ethyl). Reacting XXXXII and XXXXIV under such conditions allows for the direct formation of compounds of Formula I without the need to isolate possible intermediate compounds of Formula XXXXIII (wherein R8, R9 and Q are as defined in Formula I and wherein R his C1-C4 alkyl). Such cyclization conditions have been described in the literature, for example in J. Chem Research (12), 683-685 (2008).

[0319] A compound of formula XXXXII (wherein Q (in this Scheme 24, the arrow in Qa (respectively Qb or Qc) indicates the point of attachment to the ortho-carbon atom of the carbonyl group), R8 and R9 are as defined in formula I),

[0320] Plan 24

[0321]

[0322] The compound of formula XXXXII-1 (wherein Q, R8 and R9 are as defined in formula I, and wherein R a is C1-C4 alkyl) in the presence of a reagent such as boron tribromide or aluminum chloride, in a solvent such as dichloromethane or 1,2-dichloroethane and at a temperature ranging from -78 ° C to room temperature, under conditions known to those skilled in the art and described, for example, in J Med Chem [Journal of Medicinal Chemistry] 61, 7917-7928 (2018) (Scheme 24).

[0323] Compounds of formula XXXXII-1 (wherein Q, R8 and R9 are as defined in formula I (provided that A in Qc is nitrogen), and wherein Ra is C1-C4 alkyl) can be prepared by reacting a compound of formula VII-1 (wherein R8 and R9 are as defined in formula I, and wherein Ra is C1-C4 alkyl) with a compound of formula II-1 or II-2 or II-3a (wherein R1, R3, R3, R4, R5, R6, R7, X, A1 and A2 is as defined in formula I, and wherein Xa is a leaving group, such as, for example, chlorine, bromine or iodine, or an arylsulfonate or alkylsulfonate, such as trifluoromethanesulfonate), in the presence of a base, such as potassium carbonate or cesium carbonate, sodium hydride, sodium methoxide, sodium ethoxide or potassium tert-butoxide, in an inert solvent, such as tetrahydrofuran, tert-butyl ethyl ether, acetonitrile, dimethyl sulfoxide or N,N-dimethylamide, and at a temperature in the range of 0° C. to 80° C., preferably between 20° C. and the boiling point of the reaction mixture. Such conditions have been described in the literature, for example in Tetrahedron Letters 54, 402-405 (2013). Reaction of VII-1 with II-1 provides XXXXII-1 (wherein Q is Qa); similarly, reaction of VII-1 with II-2 provides XXXXII-1 (wherein Q is Qb); and reaction of VII-1 with II-3 provides XXXXII-1 (wherein Q is Qc) (provided that A in Qc is nitrogen).

[0324] Alternatively, a compound of formula XXXXII-1 wherein Q, R8 and R9 are as defined in formula I (provided that A in Qc is nitrogen) and wherein Ra is C1-C4 alkyl) can be prepared by reacting a compound of formula VII-1 wherein R8 and R9 are as defined in formula I and wherein Ra is C1-C4 alkyl with a compound of formula II-1 or II-2 or II-3a wherein R1, R3, R3, R4, R5, R6, R7, X, A1 and A2 are as defined in formula I and wherein Xa is a leaving group such as, for example, chloro, bromo or iodo, or an aryl sulfonate or alkyl sulfonate such as trifluoromethanesulfonic acid. Ester), in the presence of a catalyst (e.g. palladium(II) acetate, palladium(II) chloride, bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) or tris(dibenzylideneacetone)-dipalladium(0) (Pd2(dba)3, optionally in the form of a chloroform adduct), in the presence of a ligand (e.g. triphenylphosphine, BINAP or Xantphos), in the presence of a base (e.g. sodium tert-butoxide or potassium tert-butoxide, cesium carbonate or potassium carbonate), in an inert solvent (e.g. tetrahydrofuran, toluene or dioxane) and at a temperature between 60°C and 120°C, optionally under microwave irradiation. Such conditions have been described in the literature, for example in WO 2016 / 097073, CN 109956928 or Angew Chem Int Ed [Applied Chemistry International Edition] 53, 1529-1533 (2014).

[0325] A compound of formula I can be converted into another compound of formula I in a manner known per se by replacing one or more substituents of the starting compound of formula I with (another) further substituent according to the invention in a conventional manner and by subsequent modification of the compound by reactions known to those skilled in the art, such as oxidation, alkylation, reduction, acylation, Pd-catalyzed cross-coupling reactions (Buchwald-Hartwig amination, Suzuki cross-coupling, Stiller cross-coupling, Negishi cross-coupling) and other methods.

[0326] Depending on the reaction conditions and the choice of starting materials, which are appropriate in the respective case, it is possible, for example, to replace only one substituent with another substituent according to the invention in one reaction step, or to replace several substituents with other substituents according to the invention in one and the same reaction step.

[0327] Salts of compounds of formula I can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula I are obtained by treatment with a suitable acid or a suitable ion exchanger reagent, and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.

[0328] Salts of compounds of the formula I can be converted in a customary manner into the free compounds I, acid addition salts (for example by treatment with suitable basic compounds or with suitable ion exchange reagents) and salts with bases (for example by treatment with suitable acids or with suitable ion exchange reagents).

[0329] Salts of compounds of the formula I can be converted into other salts, acid addition salts of compounds of the formula I in a manner known per se, for example into other acid addition salts, for example by treating salts of inorganic acids (such as hydrochlorides) with suitable metal salts of the acid (such as sodium, barium or silver salts, for example with silver acetate) in a suitable solvent in which the inorganic salt formed (such as silver chloride) is insoluble and therefore precipitates from the reaction mixture.

[0330] Depending on the procedure or reaction conditions, those compounds of the formula I which have salt-forming properties can be obtained in free form or in the form of salts.

[0331] Depending on the number of asymmetric carbon atoms present in the molecule, the absolute and relative configuration and / or on the configuration of non-aromatic double bonds present in the molecule, the compounds of the formula I and, where appropriate, their tautomers (in each case in free form or in salt form) can be present in the form of one of the possible isomers or as a mixture of these, for example in the form of pure isomers, such as enantiomers and / or diastereomers, or as isomer mixtures, such as enantiomeric mixtures, for example racemates, diastereomeric mixtures or racemic mixtures; the present invention relates to the pure isomers and also to all possible isomer mixtures, and the above and below are to be understood as such in each case, even if stereochemical details are not explicitly mentioned in each case.

[0332] Diastereomeric mixtures or racemic mixtures of compounds of formula I in free form or in salt form, the acquisition of which may depend on the starting materials and procedures chosen, can be separated in a known manner into the pure diastereomers or racemates on the basis of the physicochemical differences of the components, for example, by fractional crystallization, distillation and / or chromatography.

[0333] Enantiomeric mixtures obtainable in an analogous manner (e.g. racemates) can be resolved into the optical antipodes by known methods, for example by recrystallization from optically active solvents; by chromatography on chiral adsorbents, for example high performance liquid chromatography (HPLC) on acetylcellulose; by cleavage with specific immobilized enzymes with the aid of suitable microorganisms; by formation of inclusion compounds, for example using chiral crown ethers, in which only one enantiomer is complexed; or by conversion into diastereomeric salts, for example by reacting the basic end product racemate with an optically active acid (e.g. a carboxylic acid, for example camphoric acid, tartaric acid or malic acid, or a sulfonic acid, for example camphorsulfonic acid) and separating the diastereomeric mixtures obtainable in this way, for example by fractional crystallization on the basis of their different solubilities, thereby obtaining the diastereomers from which the desired enantiomer can be freed by the action of suitable reagents (e.g. a basic reagent).

[0334] Pure diastereomers or enantiomers can be obtained according to the invention not only by separation of the appropriate isomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the method according to the invention with starting materials having the appropriate stereochemistry.

[0335] N-oxides can be prepared by reacting a compound of formula I with a suitable oxidizing agent (e.g. H O / urea adduct) in the presence of an anhydride (e.g. trifluoroacetic anhydride). Such oxidations are known from the literature, for example from J. Med. Chem., 32 (12), 2561-73, 1989 or WO 2000 / 15615.

[0336] If the individual components have different biological activities, it is advantageous to isolate or synthesize the biologically more effective isomers, such as enantiomers or diastereomers or isomer mixtures, such as enantiomeric mixtures or diastereomeric mixtures, in each case.

[0337] If appropriate, the compounds of formula I and, where appropriate, their tautomers (in each case in free form or in salt form) can also be obtained in the form of hydrates and / or include other solvents, such as those which can be used for crystallization of compounds present in solid form.

[0338] The compounds according to the following Tables A-1 to A-78, B-1 to B-78, and C-1 to C-78 can be prepared according to the above methods. The following examples are intended to illustrate the present invention and show preferred compounds of formula I.

[0339] Tables A-1 to A-78 below illustrate specific compounds of the present invention.

[0340]

[0341] Table A-1 Provided are 18 compounds A-1.001 to A-1.018 of formula I-1, wherein R8 is F, R9 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0342] Table Y: Definition of substituents for R2, R3, R4 and R5

[0343]

[0344]

[0345] In Table Y and in Table A, "cycloC3" represents cyclopropyl.

[0346] For example, compound A-6.015 is

[0347]

[0348] Table A-2 Provided are 18 compounds A-2.001 to A-2.018 of formula I-1, wherein R8 is F, R9 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0349] Table A-3 Provided are 18 compounds A-3.001 to A-3.018 of formula I-1, wherein R8 is F, R9 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0350] Table A-4 Provided are 18 compounds A-4.001 to A-4.018 of formula I-1, wherein R8 is Cl, R9 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0351] Table A-5 Provided are 18 compounds A-5.001 to A-5.018 of formula I-1, wherein R8 is Cl, R9 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0352] Table A-6 Provided are 18 compounds A-6.001 to A-6.018 of formula I-1, wherein R8 is Cl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0353] Table A-7 Provided are 18 compounds A-7.001 to A-7.018 of formula I-1, wherein R8 is Br, R9 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen, and R3 is as defined in Table Y.

[0354] Table A-8 Provided are 18 compounds A-8.001 to A-8.018 of formula I-1, wherein R8 is Br, R9 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen, and R3 is as defined in Table Y.

[0355] Table A-9 Provided are 18 compounds A-9.001 to A-9.018 of formula I-1, wherein R8 is Br, R9 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0356] Table A-10 Provided are 18 compounds A-10.001 to A-10.018 of formula I-1, wherein R8 is CHF2, R9 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen, and R3 is as defined in Table Y.

[0357] Table A-11 Provided are 18 compounds A-11.001 to A-11.018 of formula I-1, wherein R8 is CHF2, R9 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0358] Table A-12 Provided are 18 compounds A-12.001 to A-12.018 of formula I-1, wherein R8 is CHF2, R9 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0359] Table A-13 Provided are 18 compounds A-13.001 to A-13.018 of formula I-1, wherein R8 is CF3, R9 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0360] Table A-14 Provided are 18 compounds A-14.001 to A-14.018 of formula I-1, wherein R8 is CF3, R9 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0361] Table A-15Provided are 18 compounds A-15.001 to A-15.018 of formula I-1, wherein R8 is CF3, R9 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0362] Table A-16 Provided are 18 compounds A-16.001 to A-16.018 of formula I-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0363] Table A-17 Provided are 18 compounds A-17.001 to A-17.018 of formula I-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0364] Table A-18 Provided are 18 compounds A-18.001 to A-18.018 of formula I-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0365] Table A-19 Provided are 18 compounds A-19.001 to A-19.018 of formula I-1, wherein R8 is F, R9 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0366] Table A-20 Provided are 18 compounds A-20.001 to A-20.018 of formula I-1, wherein R8 is F, R9 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0367] Table A-21 Provided are 18 compounds A-21.001 to A-21.018 of formula I-1, wherein R8 is F, R9 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0368] Table A-22 Provided are 18 compounds A-22.001 to A-22.018 of formula I-1, wherein R8 is Cl, R9 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0369] Table A-23Provided are 18 compounds A-23.001 to A-23.018 of formula I-1, wherein R8 is Cl, R9 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0370] Table A-24 Provided are 18 compounds A-24.001 to A-24.018 of formula I-1, wherein R8 is Cl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0371] Table A-25 Provided are 18 compounds A-25.001 to A-25.018 of formula I-1, wherein R8 is Br, R9 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0372] Table A-25 Provided are 18 compounds A-26.001 to A-26.018 of formula I-1, wherein R8 is Br, R9 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0373] Table A-27 Provided are 18 compounds A-27.001 to A-27.018 of formula I-1, wherein R8 is Br, R9 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0374] Table A-28 Provided are 18 compounds A-28.001 to A-28.018 of formula I-1, wherein R8 is CHF2, R9 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0375] Table A-29 Provided are 18 compounds A-29.001 to A-29.018 of formula I-1, wherein R8 is CHF2, R9 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0376] Table A-30 Provided are 18 compounds A-30.001 to A-30.018 of formula I-1, wherein R8 is CHF2, R9 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0377] Table A-31Provided are 18 compounds A-31.001 to A-31.018 of formula I-1, wherein R8 is CF3, R9 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0378] Table A-32 Provided are 18 compounds A-32.001 to A-32.018 of formula I-1, wherein R8 is CF3, R9 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0379] Table A-33 Provided are 18 compounds A-33.001 to A-33.018 of formula I-1, wherein R8 is CF3, R9 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0380] Table A-34 Provided are 18 compounds A-34.001 to A-34.018 of formula I-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0381] Table A-35 Provided are 18 compounds A-35.001 to A-35.018 of formula I-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0382] Table A-36 Provided are 18 compounds A-36.001 to A-36.018 of formula I-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0383] Table A-37 Provided are 18 compounds A-37.001 to A-37.018 of formula I-1, wherein R9 is F, R8 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen, and R3 is as defined in Table Y.

[0384] Table A-38 Provided are 18 compounds A-38.001 to A-38.018 of formula I-1, wherein R9 is F, R8 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen, and R3 is as defined in Table Y.

[0385] Table A-39Provided are 18 compounds A-39.001 to A-39.018 of formula I-1, wherein R9 is F, R8 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0386] Table A-40 Provided are 18 compounds A-40.001 to A-40.018 of formula I-1, wherein R9 is Cl, R8 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0387] Table A-41 Provided are 18 compounds A-41.001 to A-41.018 of formula I-1, wherein R9 is Cl, R8 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0388] Table A-42 Provided are 18 compounds A-42.001 to A-42.018 of formula I-1, wherein R9 is Cl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0389] Table A-43 Provided are 18 compounds A-43.001 to A-43.018 of formula I-1, wherein R9 is Br, R8 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0390] Table A-44 Provided are 18 compounds A-44.001 to A-44.018 of formula I-1, wherein R9 is Br, R8 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen, and R3 is as defined in Table Y.

[0391] Table A-45 Provided are 18 compounds A-45.001 to A-45.018 of formula I-1, wherein R9 is Br, R8 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0392] Table A-46 Provided are 18 compounds A-46.001 to A-46.018 of formula I-1, wherein R9 is CHF2, R8 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0393] Table A-47Provided are 18 compounds A-47.001 to A-47.018 of formula I-1, wherein R9 is CHF2, R8 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen, and R3 is as defined in Table Y.

[0394] Table A-48 Provided are 18 compounds A-48.001 to A-48.018 of formula I-1, wherein R9 is CHF2, R8 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0395] Table A-49 Provided are 18 compounds A-49.001 to A-49.018 of formula I-1, wherein R9 is CF3, R8 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0396] Table A-50 Provided are 18 compounds A-50.001 to A-50.018 of formula I-1, wherein R9 is CF3, R8 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0397] Table A-51 Provided are 18 compounds A-51.001 to A-51.018 of formula I-1, wherein R9 is CF3, R8 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0398] Table A-52 Provided are 18 compounds A-52.001 to A-52.018 of formula I-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is S, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0399] Table A-53 Provided are 18 compounds A-53.001 to A-53.018 of formula I-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0400] Table A-54 Provided are 18 compounds A-54.001 to A-54.018 of formula I-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0401] Table A-55Provided are 18 compounds A-55.001 to A-55.018 of formula I-1, wherein R9 is F, R8 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0402] Table A-56 Provided are 18 compounds A-56.001 to A-56.018 of formula I-1, wherein R9 is F, R8 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0403] Table A-57 Provided are 18 compounds A-57.001 to A-57.018 of formula I-1, wherein R9 is F, R8 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0404] Table A-58 Provided are 18 compounds A-58.001 to A-58.018 of formula I-1, wherein R9 is Cl, R8 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0405] Table A-59 Provided are 18 compounds A-59.001 to A-59.018 of formula I-1, wherein R9 is Cl, R8 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0406] Table A-60 Provided are 18 compounds A-60.001 to A-60.018 of formula I-1, wherein R9 is Cl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0407] Table A-61 Provided are 18 compounds A-61001 to A-61.018 of formula I-1, wherein R9 is Br, R8 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0408] Table A-62 Provided are 18 compounds A-62.001 to A-62.018 of formula I-1, wherein R9 is Br, R8 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0409] Table A-63Provided are 18 compounds A-63.001 to A-63.018 of formula I-1, wherein R9 is Br, R8 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0410] Table A-64 Provided are 18 compounds A-64.001 to A-64.018 of formula I-1, wherein R9 is CHF2, R8 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0411] Table A-65 Provided are 18 compounds A-65.001 to A-65.018 of formula I-1, wherein R9 is CHF2, R8 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen, and R2 is as defined in Table Y.

[0412] Table A-66 Provided are 18 compounds A-66.001 to A-66.018 of formula I-1, wherein R9 is CHF2, R8 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0413] Table A-67 Provided are 18 compounds A-67.001 to A-67.018 of formula I-1, wherein R9 is CF3, R8 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0414] Table A-68 Provided are 18 compounds A-68.001 to A-68.018 of formula I-1, wherein R9 is CF3, R8 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0415] Table A-69 Provided are 18 compounds A-69.001 to A-69.018 of formula I-1, wherein R9 is CF3, R8 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0416] Table A-70 Provided are 18 compounds A-70.001 to A-70.018 of formula I-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is S, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0417] Table A-71Provided are 18 compounds A-71.001 to A-71.018 of formula I-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0418] Table A-72 Provided are 18 compounds A-72.001 to A-72.018 of formula I-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0419] Table A-73 Provided are 18 compounds A-73.001 to A-73.018 of formula I-1, wherein R8 and R9 together form a group -OCF2O-, X is S, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0420] Table A-74 Provided are 18 compounds A-74.001 to A-74.018 of formula I-1, wherein R8 and R9 together form a group -OCF2O-, X is SO, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0421] Table A-75 Provided are 18 compounds A-75.001 to A-75.018 of formula I-1, wherein R8 and R9 together form a group -OCF2O-, X is SO2, R1 is CH2CH3, R2 is hydrogen and R3 is as defined in Table Y.

[0422] Table A-76 Provided are 18 compounds A-76.001 to A-76.018 of formula I-1, wherein R8 and R9 together form a group -OCF2O-, X is S, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0423] Table A-77 Provided are 18 compounds A-77.001 to A-77.018 of formula I-1, wherein R8 and R9 together form a group -OCF2O-, X is SO, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0424] Table A-78 Provided are 18 compounds A-78.001 to A-78.018 of formula I-1, wherein R8 and R9 together form a group -OCF2O-, X is SO2, R1 is CH2CH3, R3 is hydrogen and R2 is as defined in Table Y.

[0425] Tables B-1 to B-78 below further illustrate specific compounds of the present invention.

[0426]

[0427] Table B-1 Provided are 18 compounds B-1.001 to A-1.018 of formula I-2, wherein R8 is F, R9 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0428] For example, compound B-12.005 is

[0429]

[0430] Table B-2 Provided are 18 compounds B-2.001 to B-2.018 of formula I-2, wherein R8 is F, R9 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0431] Table B-3 Provided are 18 compounds B-3.001 to B-3.018 of formula I-2, wherein R8 is F, R9 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0432] Table B-4 Provided are 18 compounds B-4.001 to B-4.018 of formula I-2, wherein R8 is Cl, R9 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0433] Table B-5 Provided are 18 compounds B-5.001 to B-5.018 of formula I-2, wherein R8 is Cl, R9 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0434] Table B-6 Provided are 18 compounds B-6.001 to B-6.018 of formula I-2, wherein R8 is Cl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0435] Table B-7 Provided are 18 compounds B-7.001 to B-7.018 of formula I-2, wherein R8 is Br, R9 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0436] Table B-8Provided are 18 compounds B-8.001 to B-8.018 of formula I-2, wherein R8 is Br, R9 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0437] Table B-9 Provided are 18 compounds B-9.001 to B-9.018 of formula I-2, wherein R8 is Br, R9 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0438] Table B-10 Provided are 18 compounds B-10.001 to B-10.018 of formula I-2, wherein R8 is CHF2, R9 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0439] Table B-11 Provided are 18 compounds B-11.001 to B-11.018 of formula I-2, wherein R8 is CHF2, R9 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0440] Table B-12 Provided are 18 compounds B-12.001 to B-12.018 of formula I-2, wherein R8 is CHF2, R9 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0441] Table B-13 Provided are 18 compounds B-13.001 to B-13.018 of formula I-2, wherein R8 is CF3, R9 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0442] Table B-14 Provided are 18 compounds B-14.001 to B-14.018 of formula I-2, wherein R8 is CF3, R9 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0443] Table B-15 Provided are 18 compounds B-15.001 to B-15.018 of formula I-2, wherein R8 is CF3, R9 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0444] Table B-16Provided are 18 compounds B-16.001 to B-16.018 of formula I-2, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0445] Table B-17 Provided are 18 compounds B-17.001 to B-17.018 of formula I-2, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0446] Table B-18 Provided are 18 compounds B-18.001 to B-18.018 of formula I-2, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0447] Table B-19 Provided are 18 compounds B-19.001 to B-19.018 of formula I-2, wherein R8 is F, R9 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0448] Table B-20 Provided are 18 compounds B-20.001 to B-20.018 of formula I-2, wherein R8 is F, R9 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0449] Table B-21 Provided are 18 compounds B-21.001 to B-21.018 of formula I-2, wherein R8 is F, R9 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0450] Table B-22 Provided are 18 compounds B-22.001 to B-22.018 of formula I-2, wherein R8 is Cl, R9 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0451] Table B-23 Provided are 18 compounds B-23.001 to B-23.018 of formula I-2, wherein R8 is Cl, R9 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0452] Table B-24Provided are 18 compounds B-24.001 to B-24.018 of formula I-2, wherein R8 is Cl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0453] Table B-25 Provided are 18 compounds B-25.001 to B-25.018 of formula I-2, wherein R8 is Br, R9 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0454] Table B-25 Provided are 18 compounds B-26.001 to B-26.018 of formula I-2, wherein R8 is Br, R9 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0455] Table B-27 Provided are 18 compounds B-27.001 to B-27.018 of formula I-2, wherein R8 is Br, R9 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0456] Table B-28 Provided are 18 compounds B-28.001 to B-28.018 of formula I-2, wherein R8 is CHF2, R9 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0457] Table B-29 Provided are 18 compounds B-29.001 to B-29.018 of formula I-2, wherein R8 is CHF2, R9 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0458] Table B-30 Provided are 18 compounds B-30.001 to B-30.018 of formula I-2, wherein R8 is CHF2, R9 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0459] Table B-31 Provided are 18 compounds B-31.001 to B-31.018 of formula I-2, wherein R8 is CF3, R9 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0460] Table B-32Provided are 18 compounds B-32.001 to B-32.018 of formula I-2, wherein R8 is CF3, R9 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0461] Table B-33 Provided are 18 compounds B-33.001 to B-33.018 of formula I-2, wherein R8 is CF3, R9 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0462] Table B-34 Provided are 18 compounds B-34.001 to B-34.018 of formula I-2, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0463] Table B-35 Provided are 18 compounds B-35.001 to B-35.018 of formula I-2, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0464] Table B-36 Provided are 18 compounds B-36.001 to B-36.018 of formula I-2, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0465] Table B-37 Provided are 18 compounds B-37.001 to A-1.018 of formula I-2, wherein R9 is F, R8 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0466] Table B-38 Provided are 18 compounds B-38.001 to B-38.018 of formula I-2, wherein R9 is F, R8 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0467] Table B-39 Provided are 18 compounds B-39.001 to B-39.018 of formula I-2, wherein R9 is F, R8 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0468] Table B-40Provided are 18 compounds B-40.001 to B-40.018 of formula I-2, wherein R9 is Cl, R8 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0469] Table B-41 Provided are 18 compounds B-41.001 to B-41.018 of formula I-2, wherein R9 is Cl, R8 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0470] Table B-42 Provided are 18 compounds B-42.001 to B-42.018 of formula I-2, wherein R9 is Cl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0471] Table B-43 Provided are 18 compounds B-43.001 to B-43.018 of formula I-2, wherein R9 is Br, R8 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0472] Table B-44 Provided are 18 compounds B-44.001 to B-44.018 of formula I-2, wherein R9 is Br, R8 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0473] Table B-45 Provided are 18 compounds B-45.001 to B-45.018 of formula I-2, wherein R9 is Br, R8 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0474] Table B-46 Provided are 18 compounds B-46.001 to B-46.018 of formula I-2, wherein R9 is CHF2, R8 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0475] Table B-47 Provided are 18 compounds B-47.001 to B-47.018 of formula I-2, wherein R9 is CHF2, R8 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0476] Table B-48Provided are 18 compounds B-48.001 to B-48.018 of formula I-2, wherein R9 is CHF2, R8 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0477] Table B-49 Provided are 18 compounds B-49.001 to B-49.018 of formula I-2, wherein R9 is CF3, R8 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0478] Table B-50 Provided are 18 compounds B-50.001 to B-50.018 of formula I-2, wherein R9 is CF3, R8 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0479] Table B-51 Provided are 18 compounds B-51.001 to B-51.018 of formula I-2, wherein R9 is CF3, R8 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0480] Table B-52 Provided are 18 compounds B-52.001 to B-52.018 of formula I-2, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0481] Table B-53 Provided are 18 compounds B-53.001 to B-53.018 of formula I-2, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0482] Table B-54 Provided are 18 compounds B-54.001 to B-54.018 of formula I-2, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0483] Table B-55 Provided are 18 compounds B-55.001 to B-55.018 of formula I-2, wherein R9 is F, R8 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0484] Table B-56Provided are 18 compounds B-56.001 to B-56.018 of formula I-2, wherein R9 is F, R8 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0485] Table B-57 Provided are 18 compounds B-57.001 to B-57.018 of formula I-2, wherein R9 is F, R8 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0486] Table B-58 Provided are 18 compounds B-58.001 to B-58.018 of formula I-2, wherein R9 is Cl, R8 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0487] Table B-59 Provided are 18 compounds B-59.001 to B-59.018 of formula I-2, wherein R9 is Cl, R8 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0488] Table B-60 Provided are 18 compounds B-60.001 to B-60.018 of formula I-2, wherein R9 is Cl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0489] Table B-61 Provided are 18 compounds B-61.001 to B-61.018 of formula I-2, wherein R9 is Br, R8 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0490] Table B-62 Provided are 18 compounds B-62.001 to B-62.018 of formula I-2, wherein R9 is Br, R8 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0491] Table B-63 Provided are 18 compounds B-63.001 to B-63.018 of formula I-2, wherein R9 is Br, R8 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0492] Table B-64Provided are 18 compounds B-64.001 to B-64.018 of formula I-2, wherein R9 is CHF2, R8 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0493] Table B-65 Provided are 18 compounds B-65.001 to B-65.018 of formula I-2, wherein R9 is CHF2, R8 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0494] Table B-66 Provided are 18 compounds B-66.001 to B-66.018 of formula I-2, wherein R9 is CHF2, R8 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0495] Table B-67 Provided are 18 compounds B-67.001 to B-67.018 of formula I-2, wherein R9 is CF3, R8 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0496] Table B-68 Provided are 18 compounds B-68.001 to B-68.018 of formula I-2, wherein R9 is CF3, R8 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0497] Table B-69 Provided are 18 compounds B-69.001 to B-69.018 of formula I-2, wherein R9 is CF3, R8 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0498] Table B-70 Provided are 18 compounds B-70.001 to B-70.018 of formula I-2, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0499] Table B-71 Provided are 18 compounds B-71.001 to B-71.018 of formula I-2, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0500] Table B-72Provided are 18 compounds B-72.001 to B-72.018 of formula I-2, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0501] Table B-73 Provided are 18 compounds B-73.001 to B-73.018 of formula I-2, wherein R8 and R9 together form a group -OCF2O-, X is S, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0502] Table B-74 Provided are 18 compounds B-74.001 to B-74.018 of formula I-2, wherein R8 and R9 together form a group -OCF2O-, X is SO, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0503] Table B-75 Provided are 18 compounds B-75.001 to B-75.018 of formula I-2, wherein R8 and R9 together form a group -OCF2O-, X is SO2, R1 is CH2CH3, R4 is hydrogen and R5 is as defined in Table Y.

[0504] Table B-76 Provided are 18 compounds B-76.001 to B-76.018 of formula I-2, wherein R8 and R9 together form a group -OCF2O-, X is S, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0505] Table B-77 Provided are 18 compounds B-77.001 to B-77.018 of formula I-2, wherein R8 and R9 together form a group -OCF2O-, X is SO, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0506] Table B-78 Provided are 18 compounds B-78.001 to B-78.018 of formula I-2, wherein R8 and R9 together form a group -OCF2O-, X is SO2, R1 is CH2CH3, R5 is hydrogen and R4 is as defined in Table Y.

[0507] Tables C-1 to C-78 below further illustrate specific compounds of the present invention.

[0508]

[0509] Table C-1Provided are 18 compounds C-1.001 to C-1.018 of formula I-3-1, wherein R8 is F, R9 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0510] Table Z: Definition of substituents for R6 and R7

[0511]

[0512] In Table Z and in Table C, "cycloC3" represents cyclopropyl.

[0513] For example, compound C-15.001 is

[0514]

[0515] Table C-2 Provided are 18 compounds C-2.001 to C-2.018 of formula I-3-1, wherein R8 is F, R9 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0516] Table C-3 Provided are 18 compounds C-3.001 to C-3.018 of formula I-3-1, wherein R8 is F, R9 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0517] Table C-4 Provided are 18 compounds C-4.001 to C-4.018 of formula I-3-1, wherein R8 is Cl, R9 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0518] Table C-5 Provided are 18 compounds C-5.001 to C-5.018 of formula I-3-1, wherein R8 is Cl, R9 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen, and R7 is as defined in Table Z.

[0519] Table C-6 Provided are 18 compounds C-6.001 to C-6.018 of formula I-3-1, wherein R8 is Cl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0520] Table C-7Provided are 18 compounds C-7.001 to C-7.018 of formula I-3-1, wherein R8 is Br, R9 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen, and R7 is as defined in Table Z.

[0521] Table C-8 Provided are 18 compounds C-8.001 to C-8.018 of formula I-3-1, wherein R8 is Br, R9 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen, and R7 is as defined in Table Z.

[0522] Table C-9 Provided are 18 compounds C-9.001 to C-9.018 of formula I-3-1, wherein R8 is Br, R9 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0523] Table C-10 Provided are 18 compounds C-10.001 to C-10.018 of formula I-3-1, wherein R8 is CHF2, R9 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0524] Table C-11 Provided are 18 compounds C-11.001 to C-11.018 of formula I-3-1, wherein R8 is CHF2, R9 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen, and R7 is as defined in Table Z.

[0525] Table C-12 Provided are 18 compounds C-12.001 to C-12.018 of formula I-3-1, wherein R8 is CHF2, R9 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0526] Table C-13 Provided are 18 compounds C-13.001 to C-13.018 of formula I-3-1, wherein R8 is CF3, R9 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0527] Table C-14 Provided are 18 compounds C-14.001 to C-14.018 of formula I-3-1, wherein R8 is CF3, R9 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0528] Table C-15Provided are 18 compounds C-15.001 to C-15.018 of formula I-3-1, wherein R8 is CF3, R9 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0529] Table C-16 Provided are 18 compounds C-16.001 to C-16.018 of formula I-3-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0530] Table C-17 Provided are 18 compounds C-17.001 to C-17.018 of formula I-3-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0531] Table C-18 Provided are 18 compounds C-18.001 to C-18.018 of formula I-3-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0532] Table C-19 Provided are 18 compounds C-19.001 to C-19.018 of formula I-3-1, wherein R8 is F, R9 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Z.

[0533] Table C-20 Provided are 18 compounds C-20.001 to C-20.018 of formula I-3-1, wherein R8 is F, R9 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Z.

[0534] Table C-21 Provided are 18 compounds C-21.001 to C-21.018 of formula I-3-1, wherein R8 is F, R9 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Z.

[0535] Table C-22 Provided are 18 compounds C-22.001 to C-22.018 of formula I-3-1, wherein R8 is Cl, R9 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Z.

[0536] Table C-23Provided are 18 compounds C-23.001 to C-23.018 of formula I-3-1, wherein R8 is Cl, R9 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Z.

[0537] Table C-24 Provided are 18 compounds C-24.001 to C-24.018 of formula I-3-1, wherein R8 is Cl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Z.

[0538] Table C-25 Provided are 18 compounds C-25.001 to C-25.018 of formula I-3-1, wherein R8 is Br, R9 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Z.

[0539] Table C-25 Provided are 18 compounds C-26.001 to C-26.018 of formula I-3-1, wherein R8 is Br, R9 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Z.

[0540] Table C-27 Provided are 18 compounds C-27.001 to C-27.018 of formula I-3-1, wherein R8 is Br, R9 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Z.

[0541] Table C-28 Provided are 18 compounds C-28.001 to C-28.018 of formula I-3-1, wherein R8 is CHF2, R9 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Z.

[0542] Table C-29 Provided are 18 compounds C-29.001 to C-29.018 of formula I-3-1, wherein R8 is CHF2, R9 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Z.

[0543] Table C-30 Provided are 18 compounds C-30.001 to C-30.018 of formula I-3-1, wherein R8 is CHF2, R9 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Z.

[0544] Table C-31Provided are 18 compounds C-31.001 to C-31.018 of formula I-3-1, wherein R8 is CF3, R9 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Z.

[0545] Table C-32 Provided are 18 compounds C-32.001 to C-32.018 of formula I-3-1, wherein R8 is CF3, R9 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Z.

[0546] Table C-33 Provided are 18 compounds C-33.001 to C-33.018 of formula I-3-1, wherein R8 is CF3, R9 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Z.

[0547] Table C-34 Provided are 18 compounds C-34.001 to C-34.018 of formula I-3-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Z.

[0548] Table C-35 Provided are 18 compounds C-35.001 to C-35.018 of formula I-3-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Z.

[0549] Table C-36 Provided are 18 compounds C-36.001 to C-36.018 of formula I-3-1, wherein R8 is 4-F-phenyl, R9 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Z.

[0550] Table C-37 Provided are 18 compounds C-37.001 to C-1.018 of formula I-3-1, wherein R9 is F, R8 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Z.

[0551] Table C-38 Provided are 18 compounds C-38.001 to C-38.018 of formula I-3-1, wherein R9 is F, R8 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen, and R7 is as defined in Table Y.

[0552] Table C-39Provided are 18 compounds C-39.001 to C-39.018 of formula I-3-1, wherein R9 is F, R8 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0553] Table C-40 Provided are 18 compounds C-40.001 to C-40.018 of formula I-3-1, wherein R9 is Cl, R8 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0554] Table C-41 Provided are 18 compounds C-41.001 to C-41.018 of formula I-3-1, wherein R9 is Cl, R8 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0555] Table C-42 Provided are 18 compounds C-42.001 to C-42.018 of formula I-3-1, wherein R9 is Cl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0556] Table C-43 Provided are 18 compounds C-43.001 to C-43.018 of formula I-3-1, wherein R9 is Br, R8 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0557] Table C-44 Provided are 18 compounds C-44.001 to C-44.018 of formula I-3-1, wherein R9 is Br, R8 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen, and R7 is as defined in Table Y.

[0558] Table C-45 Provided are 18 compounds C-45.001 to C-45.018 of formula I-3-1, wherein R9 is Br, R8 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0559] Table C-46 Provided are 18 compounds C-46.001 to C-46.018 of formula I-3-1, wherein R9 is CHF2, R8 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0560] Table C-47Provided are 18 compounds C-47.001 to C-47.018 of formula I-3-1, wherein R9 is CHF2, R8 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen, and R7 is as defined in Table Y.

[0561] Table C-48 Provided are 18 compounds C-48.001 to C-48.018 of formula I-3-1, wherein R9 is CHF2, R8 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0562] Table C-49 Provided are 18 compounds C-49.001 to C-49.018 of formula I-3-1, wherein R9 is CF3, R8 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0563] Table C-50 Provided are 18 compounds C-50.001 to C-50.018 of formula I-3-1, wherein R9 is CF3, R8 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0564] Table C-51 Provided are 18 compounds C-51.001 to C-51.018 of formula I-3-1, wherein R9 is CF3, R8 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0565] Table C-52 Provided are 18 compounds C-52.001 to C-52.018 of formula I-3-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0566] Table C-53 Provided are 18 compounds C-53.001 to C-53.018 of formula I-3-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0567] Table C-54 Provided are 18 compounds C-54.001 to C-54.018 of formula I-3-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0568] Table C-55Provided are 18 compounds C-55.001 to C-55.018 of formula I-3-1, wherein R9 is F, R8 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0569] Table C-56 Provided are 18 compounds C-56.001 to C-56.018 of formula I-3-1, wherein R9 is F, R8 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Y.

[0570] Table C-57 Provided are 18 compounds C-57.001 to C-57.018 of formula I-3-1, wherein R9 is F, R8 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0571] Table C-58 Provided are 18 compounds C-58.001 to C-58.018 of formula I-3-1, wherein R9 is Cl, R8 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Y.

[0572] Table C-59 Provided are 18 compounds C-59.001 to C-59.018 of formula I-3-1, wherein R9 is Cl, R8 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Y.

[0573] Table C-60 Provided are 18 compounds C-60.001 to C-60.018 of formula I-3-1, wherein R9 is Cl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0574] Table C-61 Provided are 18 compounds C-61.001 to C-61.018 of formula I-3-1, wherein R9 is Br, R8 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0575] Table C-62 Provided are 18 compounds C-62.001 to C-62.018 of formula I-3-1, wherein R9 is Br, R8 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen, and R6 is as defined in Table Y.

[0576] Table C-63Provided are 18 compounds C-63.001 to C-63.018 of formula I-3-1, wherein R9 is Br, R8 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0577] Table C-64 Provided are 18 compounds C-64.001 to C-64.018 of formula I-3-1, wherein R9 is CHF2, R8 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0578] Table C-65 Provided are 18 compounds C-65.001 to C-65.018 of formula I-3-1, wherein R9 is CHF2, R8 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0579] Table C-66 Provided are 18 compounds C-66.001 to C-66.018 of formula I-3-1, wherein R9 is CHF2, R8 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0580] Table C-67 Provided are 18 compounds C-67.001 to C-67.018 of formula I-3-1, wherein R9 is CF3, R8 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0581] Table C-68 Provided are 18 compounds C-68.001 to C-68.018 of formula I-3-1, wherein R9 is CF3, R8 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0582] Table C-69 Provided are 18 compounds C-69.001 to C-69.018 of formula I-3-1, wherein R9 is CF3, R8 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0583] Table C-70 Provided are 18 compounds C-70.001 to C-70.018 of formula I-3-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is S, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0584] Table C-71Provided are 18 compounds C-71.001 to C-71.018 of formula I-3-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0585] Table C-72 Provided are 18 compounds C-72.001 to C-72.018 of formula I-3-1, wherein R9 is 4-F-phenyl, R8 is hydrogen, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0586] Table C-73 Provided are 18 compounds C-73.001 to C-73.018 of formula I-3-1, wherein R8 and R9 together form a group -OCF2O-, X is S, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0587] Table C-74 Provided are 18 compounds C-74.001 to C-74.018 of formula I-3-1, wherein R8 and R9 together form a group -OCF2O-, X is SO, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0588] Table C-75 Provided are 18 compounds C-75.001 to C-75.018 of formula I-3-1, wherein R8 and R9 together form a group -OCF2O-, X is SO2, R1 is CH2CH3, R6 is hydrogen and R7 is as defined in Table Y.

[0589] Table C-76 Provided are 18 compounds C-76.001 to C-76.018 of formula I-3-1, wherein R8 and R9 together form a group -OCF2O-, X is S, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0590] Table C-77 Provided are 18 compounds C-77.001 to C-77.018 of formula I-3-1, wherein R8 and R9 together form a group -OCF2O-, X is SO, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0591] Table C-78 Provided are 18 compounds C-78.001 to C-78.018 of formula I-3-1, wherein R8 and R9 together form a group -OCF2O-, X is SO2, R1 is CH2CH3, R7 is hydrogen and R6 is as defined in Table Y.

[0592] The compounds of formula I according to the invention are active ingredients of preventive and / or therapeutic value in the field of pest control. They have a very favorable biocidal spectrum even at low application rates and are well tolerated by warm-blooded species, fish, and plants. The active ingredients according to the invention act on all or individual developmental stages of normally sensitive and also resistant animal pests (such as insects or representatives of the order Acarina). The insecticidal or acaricidal activity of the active ingredients according to the invention can manifest itself directly, i.e., destruction of the pests occurs immediately or only after a certain period of time (e.g., during molting), or indirectly, for example, by reducing egg laying and / or hatching rates, corresponding to a good activity of at least 50% to 60% destruction (mortality).

[0593] Examples of the animal pests mentioned above are:

[0594] From the order Acarina, e.g.

[0595] Acalitus spp., Aculus spp., Acaricalus spp., Aceria spp., Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp., Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp., Eotetranychus spp., Eriophyes spp.), Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Olygonychus spp., Ornithodoros spp., Polyphagotarsone latus, Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp., Polyphagotarsonemus spp., Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp.), Steneotarsonemus spp., Tarsonemus spp., and Tetranychus spp.;

[0596] From the order Phthirus, e.g.

[0597] Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp., and Phylloxera spp.;

[0598] From the order Coleoptera, e.g.

[0599] Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp., Astylus atromaculatus, Ataenius spp., Atomaria linearis, Chaetocnema tibialis, Cerotoma spp., Conoderus spp., Cosmopolites spp., Cotinis nitida, Curculio spp., Cyclocephala spp., Dermestes spp., Diabrotica spp.), Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemushampei, Lagria vilosa, Leptinotarsa ​​decemLineata, Lissorhoptrus spp., Liogenys spp., Maecolaspis spp., Maladera castanea, Megascelis spp., Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp., Phlyctinus spp.), Popillia spp., Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Somaticus spp.), Cryptorhynchus spp., Sternechus subsignatus, Tenebrio spp., Tribolium spp., and Trogoderma spp.;

[0600] From the order Diptera, e.g.

[0601] Aedes spp., Anopheles spp., Antherigonas occata., Bactrocea oleae, Bibio hortulanus, Bradysia spp., Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyza tripunctata, Glossina spp.), Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis spp., Riveria quadrifasciata, Scatella spp., Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp.) and Tipula spp.;

[0602] From the order Hemiptera, e.g.

[0603] Acanthocoris scabrator, Acrosternum spp., Adelphocoris lineolatus, Amblypelta nitida, Bathycoeliathalassina, Acanthocoris spp., Clavigralla tomentosicollis, Creontiades spp., Dichelops furcatus, Edessa spp., Euschistus spp., Eurydema pulchrum, Acrosternum spp., Brown-winged stink bug, Horcias nobilellus), rice stink bug, grass stink bug, tropical scale bug, cabbage stink bug (Murgantiahistrionic), new long-margin stink bug, tobacco blind bug (Nesidiocoris tenuis), green stink bug, Nysius simulans, island stink bug, skin stink bug, wall stink bug, red assassin bug, cocoa stink bug, chestnut stink bug (Scaptocoris castanea), black stink bug (Scotinophara spp.), Thyanta spp., trypanosoma spp., cassava web stink bug (Vatigailludens);

[0604] Acyrthosium pisum, Adalges species, Agalliano ensigera, Targuiron vein psyllid, Aleurodicus species, Aleurocanthus species, sugarcane hole whitefly, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, lemon leafhopper, Nephrodisiac species, Aphididae, Aphid species, Aspidiotus species, eggplant groove aphid, Bactericera cockerelli, Aleurodicus species, Brachycaudus species, cabbage aphid, Cavariella species, Cavariella aegopodii Scop.), wax scale species, black-brown round shield scale, orange-brown round shield scale, leafhopper species, large white leafhopper (Cofana spectra), Cryptophyllum species, leafhopper species, brown soft scale, corn yellow-winged leafhopper, naked whitefly species, citrus psyllid, wheat aphid, western round tail aphid species, small green leafhopper species, apple aphid, grape leafhopper species, Gascardia species, red eucalyptus psyllid (Glycaspis brimblecombei), cabbage constrictor aphid (Hyadaphis pseudobrassicae), large tail aphid species (Hyalopterus spp.), Hyperomyzus pallidus, lemon green leafhopper (Idioscopus clypealis), African leafhopper, Laodelphax striatellus species, water-hard scale, oyster shield scale species, radish aphid (Lopaphis erysimi), Lyogenys maidis, Aphid species, Cicada species, Metcalfa pruinosa, Aphid, Cicada, Aphid species, Neotoxoptera sp, Blacktail leafhopper species, Nilaparvata spp.), pear green aphid, Odonaspis ruthae, sugarcane cotton aphid, bayberry whitefly, Caulis psyllid, Shield scale species, Gall aphid species, Corn waxhopper, Flat-horned planthopper species, Hob wart aphid, Phylloxera species, Mosella species, Mulberry white scale species, Mealybug species, Cotton blind bug (Pseudatomoscelis seriatus), Psyllid species, Cotton scale (Pulvinaria aethiopica), Toothed scale species, Quesada gigas, Electric leafhopper (Recilia dorsalis), Constrictor aphid species, Black helmet scale species, Banded leafhopper species, Aphid species, Sitobion spp., White-backed planthopper, Spissistilus triangularis festinus), Tarophagus Proserpina, aphid species, whitefly species, Tridiscus sporoboli, Trionymus spp., African psyllids, scaly scale, flame leafhopper, and Zyginidia scutellaris.

[0605] From the order Hymenoptera, e.g.

[0606] Acromyrmex, Arge spp., Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprions spp., Pogonomyrmex spp., imported fire ants, Solenopsis spp., and Vespa spp.

[0607] From the order Isoptera, e.g.

[0608] Coptotermes spp., Corniternes cumulans, Incisitermes spp., Macrotermes spp., Mastotermes spp., Microtermes spp., Reticulitermes spp.; Tropical fire ants (Solenopsis geminate)

[0609] From the order Lepidoptera, for example,

[0610] Species of the genus Long-winged Tortoise, species of the genus Brown-banded Tortoise, species of the genus Clearwing, species of the genus Noctua, cotton leafworm, species of the genus Amylois, species of the genus Mucuna, species of the genus Yellow Tortoise, species of the genus Argyresthia, species of the genus Banded Tortoise, species of the genus Spodoptera, cotton miner, corn armyworm, powdery moth, peach fruit moth, species of the genus Graminus, species of the genus Colored Tortoise, Chrysoteuchia topiaria, grape fruit moth, species of the genus Leaf Roller, species of the genus Cloud Tortoise, species of the genus Sheath Moth, Colias lesbia, Cosmophila flava), grass borer species, cabbage borer, apple anomaly moth, boxwood moth, moth moth species, boxwood moth, stem borer species, Sudan cotton bollworm, Spodoptera species, sweet potato stem borer, mealybug species, leaf moth species (Epinotias spp.), salt marsh moth (Etiella acrea), Etiella zinckinella, flower moth species, ring needle moth, yellow tussock moth species, root cutter species, Feltia jaculiferia, Grapholitas spp., cloud moth, Heliothis species, cabbage borer, leaf cutter species (Herpetogramma spp.), gypsy moth, tomato borer, Lasmopalpus lignosellus, spiral leafminer, leafminer species, grape flower moth, Loxostege bifidalis, tussock moth species, miner species, Malacosoma spp., cabbage armyworm, tobacco hornworm, Mythimna spp., noctuid species, fall moth species, Orniodes indica, European corn borer, microtomidae species, brown moth species, small-eyed moth, stem borer, red bell moth, coffee leaf miner, one-star armyworm, potato moth, cabbage butterfly, Pieris species, diamondback moth (Plutellaxylostella), white nest moth species, leaf moth species, mint ash moth (Rachiplusia nu), western bean incense (Richia albicosta), white grain borer species (Scirpophaga spp.), Spodoptera species, Cyprinodon species, Spodoptera species, Cotton leaf roller, Cnaphalocrocis species, Heteroptera species, Trichoplusia species, Tomato leafminer, and Lymantria species;

[0611] From the order Mallophaga, for example,

[0612] Damalina spp. and Trichodectes spp.;

[0613] From the order Orthoptera, for example,

[0614] Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscus spp., and Schistocerca spp.;

[0615] From the order Psocoptera, for example,

[0616] Liposcelis spp.;

[0617] From the order Siphonaptera, for example,

[0618] Ceratophyllus spp., Ctenocephalides spp., and Xenopsylla cheopis;

[0619] From the order Thysanoptera, for example,

[0620] Calliothrips phaseoli, Frankliniella spp., Heliothrips spp., Hercinothrips spp., Parthenothrips spp., Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp.

[0621] From the order of the Thysanura, for example, Lepisma saccharina.

[0622] The active ingredients according to the invention can be used for controlling, i.e. suppressing or destroying harmful organisms of the above-mentioned type, which occur in particular on plants, especially on useful and ornamental plants in agriculture, horticulture and forestry, or on organs of such plants, such as fruits, flowers, leaves, stems, tubers or roots, and in some cases even plant organs formed at a later point in time still remain protected against these harmful organisms.

[0623] In particular, suitable target crops are cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beets, such as sugar beets or fodder beets; fruits, such as pome, stone or soft fruit, such as apples, pears, plums, peaches, apricots, cherries or berries, such as strawberries, raspberries or blackberries; leguminous crops, such as beans, lentils, peas or soybeans; oilseed crops, such as rapeseed, mustard, poppy, olives, sunflower, coconut, castor, cocoa, beans or peanuts; cucurbits such as pumpkin, cucumber, or melon; fiber plants such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits, or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, or bell peppers; lauraceae such as avocado, cinnamon, or camphor; and also tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper, grapevines, hops, plantago, and latex plants.

[0624] The compositions and / or methods of the present invention may also be used on any ornamental and / or vegetable crop, including flowers, shrubs, broadleaf trees, and evergreen plants.

[0625] For example, the present invention can be used on any of the following ornamental plant species: Ageratum species, Alonsoa species, Anemone species, Anisodontea capsenisis, Anthemis species, Antirrhinum species, Aster species, Begonia species (e.g., Rieger Begonia, Begonia sempervirens, Begonia tubéreux), Bougainvillea species, Brachycome species, Brassica species (ornamental plants), Calceolaria species, Capsicum species, Catharanthus roseus, Canna species, Centaurea species, Chrysanthemum species, Cineraria species (C. maritime), Coreopsis species, Crassula coccinea, Cupheaignea, Dahlia species, Delphinium species, Dicentra species, Dorotheantus species spp.), Lisianthus, Forsythia species, Fuchsia species, Geranium gnaphalium, Gerbera species, Globe amaranth, Heliotrope species, Sunflower species, Hibiscus species, Hydrangea species, Hydrangea species, Rhododendron, Impatiens species (African balsam), Amaranth species (Iresines spp.), Kalanchoe species, Lantana, March flower, Lion's ear, Lilium species, Mesembryanthemum species, Physalis species, Monarda species, Dracaena species, Marigold species, Dianthus species (carnation), Canna species, Oxalis species, Daisy species, Pelargonium species (Shieldleaf Pelargonium, Horseshoe Pelargonium), Viola species (Viola tricolor), Petunia species, Phlox species, Plecthranthus species spp.), poinsettia species, creeper species (five-leaf creeper, Parthenocissus quinquefolia), primula species, ranunculus species, azalea species, Rosa species (roses), rudbeckia species, African violet species, salvia species, Scaevola aemola, Schizanthus wisetonensis, sedum species, Solanum species, Surfinia petunia species (Surfinia spp.), marigold species, Nicotiana species, verbena species, zinnia species, and other bedding plants.

[0626] For example, the present invention can be used on any of the following vegetable species: Allium (garlic, onion, shallot (A.oschaninii), leek, shallot, scallion), beet parsley, celery, asparagus, beet, Brassica (Brassica oleracea, Chinese cabbage, turnip), peppers, chickpeas, endive, chicory (chicory, endive), watermelon, Cucurbita (cucumber, cantaloupe), Cucurbita (zucchini, Indian pumpkin), Cynara (artichoke, cardoon), carrot, fennel, Hypericum, lettuce, Lycopersicon (tomato, cherry tomato), mint, basil, parsley, Phaseolus (bean, pea), pea, radish, edible rhubarb, rosemary, sage, black salsify, eggplant, spinach, Valerian (V.eriocarpa), and broad bean.

[0627] Preferred ornamental plant species include African violet, begonia, dahlia, gerbera, hydrangea, verbena, rose, kalanchoe, poinsettia, aster, cornflower, coreopsis, delphinium, monarda, phlox, rudbeckia, sedum, petunia, violet, impatiens, geranium, chrysanthemum, ranunculus, fuchsia, salvia, hydrangea, rosemary, sage, St. John's wort, mint, sweet pepper, tomato, and cucumber.

[0628] The active ingredients according to the invention are particularly suitable for controlling the bean aphid, cucumber leaf beetle (Diabrotica balteata), tobacco budworm, peach aphid, diamondback moth and sea armyworm (Spodopteralittoralis) on cotton, vegetables, corn, rice and soybean crops. The active ingredients according to the invention are also particularly suitable for controlling the cabbage looper (preferably on vegetables), the codling moth (preferably on apples), the green leafhopper (preferably on vegetables, in vineyards), the potato leaf beetle (Leptinotarsa) (preferably on potatoes) and the striped stem borer (preferably on rice).

[0629] In a further aspect, the present invention may also relate to a method for controlling damage to plants and parts thereof by plant-parasitic nematodes (endoparasitic, semi-endoparasitic and ectoparasitic nematodes), in particular the following plant-parasitic nematodes, such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other species of root knot nematodes; cyst-forming nematodes, Globodera rostochiensis and other species of Globodera; Heterodera avenae, Heteroderaglycines, Heterodera exigua and other species of Globodera; 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, nematodes), Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stemand bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci, and other Ditylenchus species; Awlnematodes, Dolichodorus species;Spiral nematodes, Heliocotylenchus multicinctus, and other species of the genus Helicotylenchus; Sheath and sheathoid nematodes, species of the genera Hemicycliophora, and species of the genera Hemicriconemoides; Hirshmanniella species; Lancenematodes, species of the genus Hoploaimus; False rootknot nematodes, species of the genus Nacobbus; Needle nematodes, Longidoruse longatus, and other species of the genus Longidorus; Pin nematodes, species of the genus Pratylenchus; Lesion nematodes. nematodes), Pratylenchus negletus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi, and other Pratylenchus species; Burrowing nematodes, Radopholus similis, and other Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis, 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, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.

[0630] The compounds of the present invention may also have activity against mollusks. Examples include, for example, the family Pomacea; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus); Bradybaenidae (Bradybaena fruticum); Cepaea (Cepaea hortensis, C. nemoralis); Ochlodina; Deroceras (C. spp.); Gray slugs (D. agrestis, D. empiricorum, D. laeve, D. reticulatum); Discus (D. rotundatus); Euomphalia; Galba (G. trunculata); Helicelia (H. itala, H. obvia); Helicidae (Helicigona arbustorum; Helicodiscus; Helix (H. aperta); Limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus); Lymnaea; Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.

[0631] The term "crops" is to be understood as also including crop plants which have been transformed by the use of recombinant DNA techniques so as to enable them to synthesize one or more selectively acting toxins, such as are known, for example, from toxigenic bacteria, in particular those of the genus Bacillus.

[0632] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, for example, insecticidal proteins from Bacillus cereus or Bacillus japonicus; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vips), for example Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins of bacterial colonizing nematodes, for example, Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophila, or Xenorhabdus spp. nematophilus); toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins and other insect-specific neurotoxins; toxins produced by fungi, such as streptomycin, plant lectins, such as pea lectin, barley lectin or snowdrop lectin; agglutinin; protease inhibitors, such as trypsin inhibitor, silk proteinase inhibitor, potato glycoprotein, cystatin, papain inhibitor; ribosome inactivating protein (RIP), such as ricin, maize-RIP, abrin, luffain, saporin or bryophyllin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysteroid inhibitors, HMG-COA-reductase, ion channel blockers, such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0633] In the context of the present invention, δ-endotoxins (e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C) or vegetative insecticidal proteins (Vips) (e.g., Vip1, Vip2, Vip3, or Vip3A) are understood to include, but are not limited to, mixed toxins, truncated toxins, and modified toxins. Mixed toxins are recombinantly produced by combining different domains of those proteins (see, e.g., WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of a naturally occurring toxin are replaced. In such amino acid replacements, it is preferred that a non-naturally occurring protease recognition sequence be inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0634] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed in, for example, EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073.

[0635] Methods for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367474, EP-A-0 401 979 and WO 90 / 13651.

[0636] The toxins contained in the transgenic plants confer tolerance to harmful insects. Such insects can be found in any insect taxonomic group, but are particularly common among beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera).

[0637] Transgenic plants comprising one or more genes encoding insecticide resistance and expressing one or more toxins are known and some are commercially available. Examples of such plants are: (Zea mays variety expressing Cry1Ab toxin); YieldGard (maize variety expressing Cry3Bb1 toxin); YieldGard (Zea mays varieties expressing Cry1Ab and Cry3Bb1 toxins); (Zea mays variety expressing Cry9C toxin); Herculex (a maize variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) that confers tolerance to the herbicide glufosinate-ammonium); NuCOTN (cotton variety expressing Cry1Ac toxin); Bollgard (cotton variety expressing Cry1Ac toxin); Bollgard (cotton varieties expressing Cry1Ac and Cry2Ab toxins); (cotton variety expressing Vip3A and Cry1Ab toxins); (potato variety expressing Cry3A toxin); GT Advantage (GA21 glyphosate tolerance trait), CB Advantage (Bt11 corn borer (CB) trait) and

[0638] Further examples of such genetically modified crops are:

[0639] 1. Bt11 maize, from Syngenta Seeds SAS, 27 Chemin de l'Hobit, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. This genetically modified maize is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenicly expresses the PAT enzyme to confer tolerance to the herbicide glufosinate-ammonium.

[0640] 2. Bt176 maize, from Syngenta Seeds, 27 Rue de Hobbit, F-31 790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. This genetically modified maize is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of the Cry1Ab toxin. Bt176 maize also transgenicly expresses the PAT enzyme to confer tolerance to the herbicide glufosinate-ammonium.

[0641] 3. MIR604 maize, from Syngenta Seeds, 27 Rue de Hobbit, F-31790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. This maize plant is rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055, modified by insertion of a cathepsin G protease recognition sequence. The preparation of these transgenic maize plants is described in WO 03 / 018810.

[0642] 4. MON 863 maize, from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and confers resistance to certain coleopteran insects.

[0643] 5. IPC 531 cotton, from Monsanto Europe SA, 270-272 Avenue Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0644] 6.1507 maize, from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1F for resistance to certain lepidopteran insects and the protein PAT for tolerance to the herbicide glufosinate.

[0645] 7. NK603×MON 810 maize, from Monsanto Europe, 270-272 Boulevard Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. This is a conventionally bred hybrid maize variety, constructed by crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 maize transgenically expresses the protein CP4 EPSPS obtained from the Agrobacterium strain CP4, conferring herbicide tolerance. (contains glyphosate), and also the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstakia, which confers resistance to certain lepidopteran insects, including the European corn borer.

[0646] Transgenic crops of insect-resistant plants are also described in the BATS (Zentrum für Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) report 2003 ( http: / / bats.ch )middle.

[0647] The term "crop" should be understood to also include crop plants that have been transformed using recombinant DNA technology to enable them to synthesize selectively acting antipathogenic substances, such as, for example, so-called "pathogenesis-related proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesizing such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818, and EP-A-0 353 191. Methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above.

[0648] Crops can also be modified to enhance resistance to fungal (eg, Fusarium, Anthracnose, or Phytophthora), bacterial (eg, Pseudomonas), or viral (eg, Potato Leaf Roll Virus, Tomato Spotted Wilt Virus, Cucumber Mosaic Virus) pathogens.

[0649] Crops also include those with enhanced resistance to nematodes, such as Heterodera glycines.

[0650] Crops with tolerance to abiotic stress include those with enhanced tolerance to drought, high salinity, high temperature, cold, frost or light radiation, for example, through expression of NF-YB or other proteins known in the art.

[0651] Antipathogenic substances that can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers of sodium channels and calcium channels, for example viral KP1, KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; so-called "pathogenesis-related proteins" (PRPs; see, for example, EP-A-0 392 225); antipathogenic substances produced by microorganisms, such as peptide antibiotics or heterocyclic antibiotics (see, for example, WO 95 / 33818) or proteins or polypeptide factors which are involved in plant pathogen defense (so-called "plant disease resistance genes", as described in WO 03 / 000906).

[0652] Further areas of use of the compositions according to the invention are the protection of stored goods and storage rooms and the protection of raw materials such as wood, textiles, floor coverings or buildings, and also in the hygiene sector, in particular the protection of humans, domestic animals and productive livestock from pests of the types mentioned.

[0653] The present invention also provides a method for controlling pests (such as mosquitoes and other disease vectors; see also http: / / www.who.int / malaria / vector_control / irs / en / ). In one embodiment, the method for controlling pests comprises applying the composition of the present invention to the target pests, to their locus, or to a surface or substrate by painting, rolling, spraying, spreading, or dipping. By way of example, IRS (indoor residual spraying) application to surfaces (such as walls, ceilings, or floor surfaces) is contemplated by the methods of the present invention. In another embodiment, application of such compositions to substrates, such as nonwoven or fabric materials in the form of (or for use in the manufacture of) netting, coverings, bedding, curtains, and tents is contemplated.

[0654] In one embodiment, the method for controlling this type of harmful organism comprises to target harmful organism, to their place or to surface or substrate using the composition of the present invention of pesticidal effective dose, so that on this surface or substrate, effective retained pesticidal activity is provided.This application can be carried out by brushing, rolling, spraying, spreading or dipping pesticidal composition of the present invention.By way of example, considered by method of the present invention that the IRS of surface (as wall, ceiling or floor surface) is used, so that on this surface, effective retained pesticidal activity is provided.In another embodiment, considered using this type of composition for the residual control of the harmful organism on substrate, this substrate is as the fabric material with the form (or can be used in the manufacture of these articles) of netting, covering, quilt, curtain and tent.

[0655] The substrate to be treated (including nonwovens, fabrics or nettings) can be made of natural fibers such as cotton, raffia, jute, flax, sisal, burlap or wool, or synthetic fibers such as polyamide, polyester, polypropylene, polyacrylonitrile, etc. Polyester is particularly suitable. Methods for treating textiles are known, for example WO 2008 / 151984, WO 2003 / 034823, US 5631072, WO 2005 / 64072, WO 2006 / 128870, EP 1724392, WO 2005113886 or WO 2007 / 090739.

[0656] A further field of use of the compositions according to the invention is the field of tree injection / trunk treatment of all ornamental trees and all kinds of fruit and nut trees.

[0657] In the field of tree injection / trunk treatment, the compounds according to the invention are particularly suitable for combating wood-boring insects from the orders Lepidoptera and from the orders Coleoptera mentioned above, in particular against the wood-boring insects listed in Tables A and B below:

[0658] Table A. Examples of economically important exotic wood-boring insects.

[0659]

[0660] Table B. Examples of economically important native wood-boring insects.

[0661]

[0662]

[0663]

[0664]

[0665] The present invention can also be used to control any insect pest that may be present in turfgrass, including, for example, beetles, caterpillars, fire ants, ground pearls, millipedes, woodlice, mites, mole crickets, scale insects, mealybugs, ticks, cicadas, southern wheat stink bugs, and white grubs. The present invention can be used to control insect pests at all stages of their life cycle, including eggs, larvae, nymphs, and adults.

[0666] In particular, the present invention can be used to control insect pests that feed on the roots of turfgrasses, including grubs (such as Cyclocephala spp. (e.g., marked beetles, C. lurida), Rhizotrogus spp. (e.g., European beetles, European root beetles (R. majalis)), Cotinus spp. (e.g., Green June beetles, C. nitida), Popillia spp. (e.g., Japanese beetles, P. japonica), Phyllophaga spp. (e.g., May / June beetles), Ataenius spp. (e.g., Black turfgrass ataenius, A. spretulus), Maladera spp. (e.g., Asiatic garden beetles, A. spp.), and other insect pests. beetle, M. castanea, and Tomarus genera), ground pearls (Margarodes spp.), mole crickets (tawny, southern, and short-winged; Scapteriscus spp., Gryllotalpa africana), and leatherjackets (European crane fly, Tipula spp.).

[0667] The present invention can also be used to control insect pests of turfgrass in thatched homes, including armyworms (such as the fall armyworm Spodoptera frugiperda, and the common armyworm Pseudaletia unipuncta), cutworms, weevils (Sphenophorus spp., such as S. venatus vertitus and S. parvulus), and meadow moths (such as Crambus spp. and the tropical meadow moth, Herpetogramma phaeopteralis).

[0668] The present invention can also be used to control insect pests in turfgrasses that live above ground and feed on turfgrass leaves, including wheat stink bugs (such as the southern wheat stink bug, Blissus insularis), Bermudagrass mite (Eriophyes cynodoniensis), Grass mealybug (Antonina graminis), Propsapia bicincta, leafhoppers, cutworms (Noctuidae), and Schizaphis graminis.

[0669] The present invention can also be used to control other pests in turfgrass, such as introduced fire ants (Solenopsis invicta) that create nests in lawns.

[0670] In the hygiene sector, the compositions according to the invention are effective against epiparasites such as hard ticks, soft ticks, scabies, autumn mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.

[0671] Examples of such parasites are:

[0672] From the order of the Pediculus: Haemaphysalis spp., Linognathus spp., Pediculus hominis spp., and Phtirus spp., Phitirus spp.

[0673] From the order Trichophagus: Felicola species, Felicola species, Felicola species, Felicola species, Werneckiella spp., Lepikentron spp., Felicola species, Felicola species, and Felicola species.

[0674] From the order Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp. spp.), Musca spp., Hydrotaea spp., Biting flies spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. spp.) and Melophagus spp.

[0675] From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllum spp.

[0676] From the order of the Heteropterida, for example, Cimex spp., Triatominae spp., Panstrongylus spp.

[0677] From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattelagermanica and Supella spp.

[0678] Subclass Acaria (family Acarida) and orders Meta-stigmata and Meso-stigmata, for example, Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., and Varroa spp.

[0679] From the orders Actinedida (Prostigmata) and Acaridida (Astigmata), for example, 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. spp.), Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcooptes spp., Notoedress spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp.

[0680] The compositions according to the invention are also suitable for protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and card, leather, floor coverings and construction materials from infestation by insects.

[0681] The compositions according to the invention can be used, for example, to combat the following pests: beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale), Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., and Dinoderus minutus, as well as Hymenoptera, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, and Urocerus augur, and termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes spp. indicola), Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, and Coptotermes formosanus, as well as borers such as Silverfish (Lepisma saccharina).

[0682] The compounds according to the invention can be used as pesticides in unmodified form, but they are generally formulated into compositions in various ways using formulation adjuvants such as carriers, solvents and surfactants. These formulations may be in different physical forms, for example, in the form of dusts, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent compressed tablets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, mobile oils, aqueous dispersions, oily dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or water-miscible organic solvents as carriers), impregnated polymer films or in other known forms, for example, from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, 1st edition, second revision (2010). Such formulations can be used directly or diluted before use. Dilution can be performed with, for example, water, liquid fertilizers, micronutrients, biological organisms, oils or solvents.

[0683] These formulations can be prepared, for example, by mixing the active ingredient with formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.

[0684] These active ingredients can also be contained in very fine microcapsules. Microcapsules contain active ingredients in porous carriers. This allows the active ingredient to be released (e.g., slowly released) into the environment in a controlled amount. Microcapsules typically have a diameter of 0.1 to 500 microns. The amount of active ingredient they contain is about 25% to 95% of the capsule weight by weight. These active ingredients can be in the form of a holistic solid, in the form of fine particles in a solid or liquid dispersion, or in the form of a suitable solution. The encapsulated membrane can include, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane or chemically modified polymers and starch xanthate or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed, in which the active ingredient is contained in a solid matrix of a base material in the form of finely dispersed particles, but these microcapsules themselves are not wrapped.

[0685] Formulation adjuvants suitable for preparing the compositions according to the invention are known per se. As liquid carriers, there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosinate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl methylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol, alkyl pyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, α-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glyceryl acetate, glyceryl diacetate, glyceryl triacetate, Hexadecane, hexanediol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, lactic acid propylene glycol Esters, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol and higher molecular weight alcohols such as amyl alcohol, tetrahydrofuranol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.

[0686] Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soy flour, pumice, wood flour, ground walnut shells, lignin, and similar materials.

[0687] Many surface-active substances can be used advantageously in both solid and liquid formulations, especially those which can be diluted with a carrier before use. Surface-active substances can be anionic, cationic, nonionic or polymeric and they can act as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium laurylsulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide addition products, such as ethoxylated nonylphenol; alcohol / alkylene oxide addition products, such as ethoxylated tridecanol; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; salts of dialkylsulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as dodecyltrimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphates; and further substances, such as are described, for example, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Company. Corp., Ridgewood New Jersey (1981).

[0688] Additional adjuvants that can be used in pesticidal formulations include crystallization inhibitors, viscosity regulators, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, substances and buffers that neutralize or vary the pH, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, glidants, lubricants, dispersants, thickeners, antifreeze agents, microbicides, and liquid and solid fertilizers.

[0689] The composition according to the invention may comprise an additive comprising an oil of plant or animal origin, a mineral oil, an alkyl ester of such an oil or a mixture of such an oil with an oil derivative. The amount of the oil additive in the composition according to the invention is generally from 0.01% to 10% based on the mixture to be applied. For example, the oil additive can be added to the spray tank in the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oil or an oil of plant origin, such as rapeseed oil, olive oil or sunflower oil; emulsified vegetable oils; alkyl esters of oils of plant origin, such as methyl derivatives; or oils of animal origin, such as fish oil or tallow. Preferred oil additives include C8-C 22 Alkyl esters of fatty acids, especially C 12 -C 18Methyl derivatives of fatty acids, such as the methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10th edition, Southern Illinois University, 2010.

[0690] The compositions of the present invention generally contain from 0.1% to 99% by weight, especially from 0.1% to 95% by weight, of a compound of the present invention and from 1% to 99.9% by weight of formulation adjuvants, preferably including from 0 to 25% by weight of surfactants. While commercial products may preferably be formulated as concentrates, the end user will generally employ dilute formulations.

[0691] The application rate varies within a wide range and depends on the nature of the soil, the application method, the crop plants, the harmful organisms to be controlled, the prevailing climatic conditions, and other factors dictated by the application method, the time of application, and the target crop. In general, the compound can be applied at a rate of from 1 l / ha to 2000 l / ha, in particular from 10 l / ha to 1000 l / ha.

[0692] A preferred formulation may have the following composition (wt %):

[0693] Emulsifiable concentrates :

[0694] Active ingredient: 1% to 95%, preferably 60% to 90%

[0695] Surfactant: 1% to 30%, preferably 5% to 20%

[0696] Liquid carrier: 1% to 80%, preferably 1% to 35%

[0697] Dust powder :

[0698] Active ingredient: 0.1% to 10%, preferably 0.1% to 5%

[0699] Solid carrier: 99.9% to 90%, preferably 99.9% to 99%

[0700] Suspension concentrate:

[0701] Active ingredient: 5% to 75%, preferably 10% to 50%

[0702] Water: 94% to 24%, preferably 88% to 30%

[0703] Surfactant: 1% to 40%, preferably 2% to 30%

[0704] wettable powder :

[0705] Active ingredient: 0.5% to 90%, preferably 1% to 80%

[0706] Surfactants: 0.5% to 20%, preferably 1% to 15%

[0707] Solid carrier: 5% to 95%, preferably 15% to 90%

[0708] Granules:

[0709] Active ingredient: 0.1% to 30%, preferably 0.1% to 15%

[0710] Solid carrier: 99.5% to 70%, preferably 97% to 85%

[0711] The following examples further illustrate (but do not limit) the present invention.

[0712]

[0713] The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable grinder to obtain a wettable powder which can be diluted with water to give a suspension of the desired concentration.

[0714] Powder for dry seed treatment a) b) c) Active ingredient 25％ 50％ 75％ Light mineral oil 5％ 5％ 5％ Highly dispersed silicic acid 5％ 5％ - Kaolin 65％ 40％ - talc - 20％

[0715] The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable grinder to obtain a dust that can be used directly for seed treatment.

[0716] <![CDATA[ Emulsifiable concentrates ]]> Active ingredient 10％ Octylphenol polyglycol ether (4-5 mol of ethylene oxide) 3％ Calcium dodecylbenzenesulfonate 3％ Castor oil polyglycol ether (35 mol of ethylene oxide) 4％ Cyclohexanone 30％ Xylene mixture 50％

[0717] Emulsions of any desired dilution which can be used in plant protection can be obtained from these concentrates by dilution with water.

[0718] <![CDATA[ Dust powder ]]> a) b) c) Active ingredient 5％ 6％ 4％ talc 95％ - - Kaolin - 94％ - Mineral fillers - - 96％

[0719] Ready-to-use dusts are obtained by mixing the combination with a carrier and grinding the mixture in a suitable grinder. Such dusts can also be used for dry seed dressing of seeds.

[0720] <![CDATA[ Extruder granules ]]> Active ingredient 15％ Sodium lignin sulfonate 2％ Carboxymethyl cellulose 1％ Kaolin 82％

[0721] The combination is mixed and ground with the adjuvants, and the mixture is moistened with water.

[0722] The mixture is extruded and then dried in a stream of air.

[0723] <![CDATA[ Coated granules ]]> Active ingredient 8％ Polyethylene glycol (molecular weight 200) 3％ Kaolin 89％

[0724] The finely ground combination is applied uniformly in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coated granules are obtained.

[0725] Suspension concentrates

[0726] Active ingredient 40％ Propylene glycol 10％ Nonylphenol polyglycol ether (15 mol of ethylene oxide) 6％ Sodium lignin sulfonate 10％ Carboxymethyl cellulose 1％ Silicone oil (as a 75% emulsion in water) 1％ water 32％

[0727] The finely ground combination is intimately mixed with adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation materials can be treated and protected against microbial infestation by spraying, pouring or immersion.

[0728] Flowable concentrate for seed treatment

[0729]

[0730] The finely ground combination is intimately mixed with adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation materials can be treated and protected against microbial infestation by spraying, pouring or immersion.

[0731] Extended-release capsule suspension

[0732] 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer, and 51.6 parts of water until the desired particle size is reached. To this emulsion, 2.8 parts of a mixture of 1,6-hexanediamine in 5.3 parts of water are added. The mixture is stirred until polymerization is complete. The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% active ingredient. The diameter of the medium capsules is 8-15 microns. The resulting formulation is applied to the seeds as an aqueous suspension in a device suitable for this purpose.

[0733] Formulation types include emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), emulsions, water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), oil dispersions (OD), oil suspensions (OF), oil-soluble concentrates (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume concentrates (UL), finished products (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG), or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0734] Preparation example:

[0735] "Mp" means melting point in °C. Free radicals represent methyl groups. Recorded on a Brucker 400 MHz spectrometer 1 H NMR measurements, chemical shifts are given in ppm relative to a TMS standard. Spectra were measured in deuterated solvents as specified. The compounds were characterized using any of the following LCMS methods. Characteristic LCMS values ​​obtained for each compound are the retention time ("Rt", reported in minutes) and the measured molecular ion (M+H) + or (MH) - .

[0736] LCMS and GCMS methods:

[0737] Method 1 :

[0738] Spectra were recorded on a mass spectrometer from Waters Corporation (SQD, SQDII or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative ions), capillary voltage: 0.8-3.00 kV, cone: 5-30 V, source temperature: 120°C-150°C, desolvation temperature: 350°C-600°C, cone gas flow: 50-150 l / h, desolvation gas flow: 650-1000 l / h, mass range: 110 to 950 Da and AcquityUPLC from Waters Corporation: binary pump, heated column compartment, diode array detector and ELSD. Column: Waters UPLC HSS T3, 1.8 μm, 30 x 2.1 mm, temperature: 60° C., DAD wavelength range (nm): 210 to 400, run time: 1.5 min; solvent: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; flow rate (ml / min) 0.85, gradient: 10% B isocratic for 0.2 min, then 10%-100% B in 1.0 min, 100% B isocratic for 0.2 min, 100%-10% B in 0.05 min, 10% B isocratic for 0.05 min.

[0739] Example P1: 3-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]- Preparation of 4-(2-(4-(2-methyl-1-thiazolyl)chromen-4-one (Compound P.1)

[0740]

[0741] Step 1: (E)-3-(dimethylamino)-1-[2-hydroxy-4-(trifluoromethyl)phenyl]prop-2-en-1-one (intermediate Preparation of INT1

[0742]

[0743] A mixture of 1-(2-hydroxy-4-trifluoromethyl)phenyl)ene ketone (4.77 g, 22.2 mmol) and N,N-dimethyl-formamide dimethyl acetal (3.84 mL, 28.9 mmol, 1.3 equiv) was stirred at 100 ° C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with water, and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed with water and then with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was used directly without any purification. LCMS (Method 1): Rt = 0.98 min, m / z 260 [M + H] + .

[0744] Step 2: Preparation of 3-iodo-7-(trifluoromethyl)chromen-4-one (Intermediate INT 2)

[0745]

[0746] To a solution of (E)-3-(dimethylamino)-1-[2-hydroxy-4-(trifluoromethyl)phenyl]prop-2-en-1-one (5.96 g, 23 mmol) in methanol (57 mL) cooled at 5 ° C. was added iodine (7.00 g, 27.6 mmol, 1.2 equiv). The reaction mixture was stirred at room temperature for 17 hours. The mixture was diluted with an aqueous sodium thiosulfate solution and stirred for 15 minutes. The formed precipitate was filtered and then dissolved in ethyl acetate. The organic phase was washed twice with brine, dried over magnesium sulfate, and concentrated in vacuo with isolute. The crude material was purified by flash chromatography on silica gel (ethyl acetate in cyclohexane) to give the desired product as an orange solid. LCMS (Method 1): Rt=1.02 min, m / z 341 [M+H] + .

[0747] Step 3: Preparation of [4-oxo-7-(trifluoromethyl)chromen-3-yl]boronic acid (Intermediate INT 3)

[0748]

[0749] To a solution of 3-iodo-7-(trifluoromethyl)chromen-4-one (0.3 g, 0.88 mmol) in THF (1.5 mL) cooled at -78°C was added isopropylmagnesium chloride lithium chloride complex (1.3 M in THF) (0.95 mL, 1.23 mmol, 1.4 equiv). The reaction mixture was stirred at -78°C for 15 minutes, then trimethyl borate (0.25 mL, 2.21 mmol, 2.5 equiv) was added. The reaction mixture was then allowed to warm to room temperature and stirred for 2 hours. The mixture was diluted with aqueous ammonium chloride, the product was extracted twice with ethyl acetate, the combined organic phases were dried over magnesium sulfate, and concentrated in vacuo. The crude material was used directly without any purification. LCMS (Method 1): Rt = 0.89 min, m / z 259 [M+H] + .

[0750] Step 4: Preparation of 3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-amine (Intermediate INT 4) preparation

[0751]

[0752] Hydrochloric acid (25 mL, 4.0 mol / L, 101.7 mmol, 10 equivalents) in 1,4-dioxane was slowly added to a solution of tert-butyl N- [3- ethylsulfonyl -7- (trifluoromethyl) imidazo [1,2-a] pyridine -2- yl] carbamate (4.0 g, 10.17 mmol) disclosed in WO2021 / 140122 in 1,4-dioxane (40.7 mL) and the mixture was heated to 50 ° C. After 15 hours, the mixture was concentrated under reduced pressure. The residue was suspended in ethyl acetate, saturated sodium bicarbonate aqueous solution was added, and the resulting mixture was extracted three times with ethyl acetate. The combined organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to give 3.0 g of 3- ethylsulfonyl -7- (trifluoromethyl) imidazo [1,2-a] pyridine -2- amine, which was used directly in the next step. 1 H NMR (400 MHz, DMSO-d6) δ ppm: 1.15 (t, 3H), 3.36 (q, 2H), 6.29 (broad s, 2H), 7.25 (dd, 1H), 7.83 (d, 1H), 8.66 (d, 1H).

[0753] Step 5: Preparation of 2-bromo-3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridine (Intermediate INT 5) preparation

[0754]

[0755] Under an argon atmosphere, 3- ethylsulfonyl -7- (trifluoromethyl) imidazo [1,2-a] pyridine -2- amine (2.5g, 8.5mmol) is dissolved in acetic acid (66mL). Then hydrobromic acid (1.9mL, 17mmol, 2 equivalents) is added dropwise to the reaction mixture within 5 minutes. Then sodium nitrite (0.55mL, 17mmol, 2 equivalents) is added in batches (exothermic). The resulting mixture is stirred at room temperature for 25 minutes. Copper bromide (I) (2.5g, 17mmol, 2 equivalents) is added in batches and the mixture is stirred at room temperature for 50 minutes. The mixture is poured into ice water and the resulting aqueous phase is extracted three times with ethyl acetate. The combined organic layer is dried over sodium sulfate, filtered, and concentrated under reduced pressure. Methanol is added to the residue and the suspension is filtered to obtain 1.64g of 2- bromo -3- ethylsulfonyl -7- (trifluoromethyl) imidazo [1,2-a] pyridine as an orange solid. LCMS (Method 5): Rt=0.99 min, m / z 283 / 285 [M+H] + . 1 H NMR (400MHz, CDCl3) δppm: 1.36 (t, 3H), 3.41 (q, 2H), 7.20-7.30 (m, 1H), 8.00 (s, 1H), 9.20 (d, 1H).

[0756] Step 6: 3-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]- 4-Chloro-1-one (compound P.1)

[0757]

[0758] To a solution of 2-bromo-3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridine (380 mg, 0.958 mmol) in acetonitrile (7.6 mL) and water (1.9 mL) were added [4-oxo-7-(trifluoromethyl)chromen-3-yl]boronic acid (247 mg, 0.958 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride complex with dichloromethane (164 mg, 0.192 mmol, 0.2 equiv) under argon atmosphere at room temperature. The mixture was stirred at 38°C for 4 hours, then [4-oxo-7-(trifluoromethyl)chromen-3-yl]boronic acid (247 mg, 0.958 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (164 mg, 0.192 mmol, 0.2 equivalents) were added and the mixture was stirred at 38°C for 18 hours. The reaction mixture was diluted with ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and evaporated to give a crude brown solid. The residue was purified by silica gel chromatography (cyclohexane / 0%-30% ethyl acetate / EtOH) to give 402 mg of material containing primarily the desired product. Methanol (5 mL) was added and the precipitate was filtered to give 134 mg of pure 3-[3-ethylsulfonyl-7-(trifluoromethyl)-imidazo[1,2-a]pyridin-2-yl]-7-(trifluoromethyl)chromen-4-one. LCMS (Method 1): Rt=1.06 min, m / z 491 [M+H] + . 1 HNMR(400MHz,CDCl3)δppm 1.49(t,3H),3.76(q,2H),7.25-7.32(m,1H),7.73(d,1H),7.88(s,1H),8.09(s,1H),8.36(s,1H),8.46(d,1H),9.09(d,1H).

[0759] Table P: Examples of compounds of formula (I)

[0760]

[0761] By adding other insecticides, acaricides and / or fungicidal active ingredients, the activity of the composition according to the present invention can be significantly widened and is suitable for general conditions. The mixture of a compound of Formula I with other insecticides, acaricides and / or fungicidal active ingredients can also have other unexpected advantages, which can also be described as synergistic activities in a wider sense. For example, better tolerance of plants, reduced phytotoxicity, insects can be controlled at their different developmental stages or better behavior during their production (for example, during grinding or mixing, during their storage or during their use).

[0762] Suitable active ingredients for addition are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

[0763] The following combinations of a compound of formula I and another active substance in a weight ratio of 1:1 are preferred (the abbreviation "TX" means "a compound selected from the group consisting of the compounds described in Tables A-1 to A-78, Tables B-1 to B-78, Tables C-1 to C-78 and Table P of the present invention"):

[0764] An auxiliary agent selected from the group consisting of: petroleum (alias) (628) + TX;

[0765] Abamectin + TX, acetamiprid + TX, acetamiprid + TX, flumethrin + TX, acynonapyr + TX, bifenapyr + TX, afoxolaner + TX, cotton bell carbendazim + TX, allethrin + TX, α-cypermethrin + TX, alpha-cypermethrin + TX, sulfamethoxazole + TX, cypermethrin + TX, triazotin + TX, sulfamethoxazole + TX, benzyltrimethoxam + TX, benzpyrimoxan + TX, β-cyfluthrin + TX, β-cypermethrin + TX, bifenazate + TX, bifenthrin + TX, binapacryl + TX, bioallethrin + TX, S-bioallethrin + TX, bio-resmethrin + TX, bistrifluan + TX, broflanilide + TX, brofluthrin + TX, bromophos-ethyl + TX, buprofezin + TX, butacarb + TX, cadusafos + TX, carbaryl + TX, butacarb + TX, batan + TX, CAS No.: 1632218-00-8+TX, CAS No.: 1808115-49-2+TX, CAS No.: 2032403-97-5+TX, CAS No.: 2044701-44-0+TX, CAS No.: 2128706-05-6+TX, CAS No.: 2095470-94-1+TX, CAS No.: 2377084 -09-6+TX、CAS No.:1445683-71-5+TX、CAS No.:2408220-94-8+TX、CAS No.:2408220-91-5+TX、CAS No.:1365070-72-9+TX、CAS No.:2171099-09-3+TX、CAS No.:2396747-83-2+TX、CAS No.:2133042-31-4+TX、CAS No.:2133042-44-9+TX、CAS No.:1445684-82-1+TX、CAS No.:1445684-82-1+TX、CAS No.:1922957-45-6+TX、CAS No.:1 922957-46-7+TX、CAS No.:1922957-47-8+TX、CAS No.:1922957-48-9+TX、CAS No.:2415706-16-8+TX、CAS No.:1594624-87-9+TX、CAS No.:1594637-65-6+TX、CAS No.:1594626-19-3+TX、CAS No.:1990457-52-7+TX、CAS No.:1990457-55-0+TX、CAS No.:1990457-57-2+TX、CAS No.:1990457-77-6+TX、CAS No.:1990457-66-3+TX、CAS No.: 1990457-85-6+TX, CAS No.: 2220132-55-6+TX, CAS No.: 1255091-74-7+TX, CAS No.: 2719848-60-7+TX, CAS No.: 1956329-03-5+TX, chlorantraniliprole+TX, chlordane+TX, chlorfenapyr+TX, chlorpromazide+TX, chloranil+TX, chlorfenapyr+TX, chlorfenapyr+TX, clenpyrine+TX, cloethocarb+TX, clothianidin+TX, 2-chlorophenyl N-methylcarbamate (CPMC)+TX, benzonitrile+TX, cyanantraniliprole+TX, cyclobromofenapyr+TX, cyclobutrifluanid+TX ram)+TX, pyrethroids+TX, cycloxanthrin+TX, cytoxanil+TX, cyetpyrafen+TX, cyetpyrafen or etpyrafen+TX, cyfluthrin+TX, cyhalodiamide+TX, cyhalothrin+TX, cypermethrin+TX, cypermethrin+TX, cyproflanilide+TX, cyromazine+TX, deltamethrin+TX, cyprofenuron+TX, chlorfenapyr ... Dimpropyridaz + TX, diprofenac + TX, dinotefuran + TX, vegetable phosphorus + TX, emamectin (or emamectin benzoate) + TX, dextromethorphine + TX, epsilon-momfluorothrin + TX, epsilon-metofluthrin + TX, cypermethrin + TX, ethion + TX, ethomethrin + TX, etoxazole + TX, fenmethrin + TX, fenazaquin + TX, fenfluramide + TX, pentothrin + TX, fenmezoditiaz + TX, fenitrothion + TX, fenobucarb + TX, fenthiocarb + TX, fenoxycarb + TX, cypermethrin + TX, azole Fenpyroximate + TX, fenpyrophos + TX, fenthion + TX, cypermethrin + TX, fipronil + TX, flometoquin + TX, flonicamid + TX, cypermethrin + TX, fluazaindolizine + TX, flupyralid + TX, flubendiamide + TX, fluchlordiniliprole + TX, flucitrinate + TX, flufenoxuron + TX, flucythrin + TX, fluthiazolin + TX, flumethrin + TX, flumethrin + TX, flumethrin + TX, flufenoxam + TX, fluchlordiniliprole + TX, flucitrinate + TX, flufenoxuron + TX, flucythrin + TX, fluthiazolin + TX, flumethrin + TX, flufenoxam + TX, flumethrin + TX, butenefipronil + TX,Fluhexafon + TX, fluchlorfenapyr + TX, fluopyram + TX, flupentiofenox + TX, flupyroxystrobin + TX, flupyrimin + TX, fluralaner + TX, fluvalinate + TX, fluxametamide + TX, thiazolin + TX, gamma-cyhalothrin + TX, pyrimidine + TX, chlorfenapyr + TX, benzyl ammonium chloride + TX, heptafluthrin + TX, hexathiazolin + TX, hydrazone + TX, imidazole Imicyafos + TX, imidacloprid + TX, imiprodinil + TX, indazapyroxamet + TX, indoxacarb + TX, iodomethane + TX, iprodione + TX, isocycloseram + TX, isosulfuron + TX, ivermectin + TX, κ-bifenthrin + TX, κ-tefluthrin + TX, λ-cyhalothrin + TX, ledprona + TX, lepidomycin + TX, lotilaner + TX, chlorfenuron + TX, metaflumizone + TX, metaldehyde + TX, methomyl + TX, methomyl + TX, methoxyfenozide + TX, metofluthrin + TX, Metformin + TX, chlorpyrifos + TX, cypermethrin + TX, momfluorothrin + TX, cypermethrin + TX, nicofluprole + TX; nitenpyram + TX, nithiazine + TX, omethoate + TX, oxamyl + TX, oxazosulfyl + TX, parathion-ethyl + TX, permethrin + TX, phenothrin + TX, phosphamidon + TX, piperonyl butoxide + TX, pirimicarb + TX, pirimiphos-ethyl + TX, pirimiphos-methyl + TX, polyhedrosis virus + TX, prallethrin + TX, profenofos + TX, proflurane + TX, gram Amitraz+TX, Amitraz+TX, Propoxur+TX, Prothiophos+TX, Protrifenbute+TX, Pyflubumide+TX, Pymetrozine+TX, Pyraclofos+TX, Pyrafluprole+TX, Pyridaben+TX, Pyridalyl+TX, Pyrifluquinazon+TX, Pyrimidine+TX, Pyriminostrobin+TX, Pyraclostrobin+TX, Pyrimethrin+TX, Pyriproxyfen+TX, Resmothrin+TX, Sarolaner+TX, Selamectin+TX, Silafluthrin+TX, Spinetoram+TX,Spinosad + TX, spirobudifen + TX; spirodiclofen + TX, spiromesifen + TX, spiropidion + TX, spirotetramat + TX, spidoxamat + TX, sulfonecarb + TX, tebufenozide + TX, tebufenpyrad + TX, tebupirimiphos + TX, tefluthrin + TX, tebufenoxam + TX, tetrachlorvinphos + TX, tetrafluthrin + TX, tetrachlorvinphos + TX, tetrachlorvinphos Tetradiphon + TX, tetramethrin + TX, tetrafluthrin + TX, acaricide + TX, flucyram + TX, θ-cypermethrin + TX, thiacloprid + TX, thiamethoxam + TX, thiocarb + TX, thiodicarb + TX, long-lasting carb + TX, methyl sulfamethoxam + TX, sulfamethoxam + TX, tigolaner + TX, tiorantraniliprole + TX; thiophene ( TX, thiamethoxam + TX, tolfenpyrad + TX, toxaphene + TX, tralomethrin + TX, transfluthrin + TX, triazophos + TX, trichlorfon + TX, chlorpyrifos + TX, trichlorfon + TX, trifluenfuronate + TX, triflumezopyrim + TX, tyclopyrazoflor + TX, ζ-cypermethrin + TX, seaweed extract and fermentation products derived from sugar acyl + TX, seaweed extract and fermentation products derived from sugar acyl (containing urea + TX, amino acids + TX, potassium and molybdenum and EDTA-chelated manganese) + TX, seaweed extract and fermented plant products + TX, seaweed extract and fermented plant products (containing plant hormones + TX, vitamins + TX, EDTA-chelated copper + TX, zinc + TX, and iron + TX), azadirachtin + TX, Bacillus ayuzawa (Bacillus aizawai) + TX, Bacillus chitinosporus AQ746 (NRRL registration number B-21 618)+TX, Bacillus firmus+TX, Bacillus kurstaki+TX, Bacillus mycoides AQ726 (NRRL Accession No. B-21664)+TX, Bacillus pumilus (NRRL Accession No. B-30087)+TX, Bacillus pumilus AQ717 (NRRL Accession No. B-21662)+TX, Bacillus species AQ178 (ATCC Accession No. 53522)+TX, Bacillus species AQ175 (ATCC Accession No. 55608)+TX, Bacillus species AQ177 (ATCC Accession No. 55609)+TX, unspecified Bacillus subtilis+TX, Bacillus subtilis AQ153 (ATCC Accession No. 55614)+TX,Bacillus subtilis AQ30002 (NRRL Accession No. B-50421) + TX, Bacillus subtilis AQ30004 (NRRL Accession No. B-50455) + TX, Bacillus subtilis AQ713 (NRRL Accession No. B-21661) + TX, Bacillus subtilis AQ743 (NRRL Accession No. B-21665) + TX, Bacillus thuringiensis AQ52 (NRRL Accession No. B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL Accession No. B-21530) + TX, Bacillus thuringiensis subsp. Kurstaki BMP 123+TX, Beauveria bassiana+TX, D-limonene+TX, Granulovirus+TX, Harpin+TX, Helicoverpa armigera nuclear polyhedrosis virus+TX, Helicoverpa tatarinowii nuclear polyhedrosis virus+TX, Helicoverpa virescens nuclear polyhedrosis virus+TX, Helicoverpa virescens nuclear polyhedrosis virus+TX, Helicoverpa australis nuclear polyhedrosis virus+TX, Metarhizium species+TX, Muscodor albus 620 (NRRL accession number 30547)+TX, Muscodor roseus A3-5 (NRRL accession number 30548)+TX, Neem-based products+TX, Paecilomyces fumosorum+TX, Paecilomyces lilacinus+TX, Pasteuria szabalensis+TX, Pasteuria penetrantis+TX, Pasteuria mycoides+TX, Pasteuria soreiroides thornei)+TX, Pasteurella+TX, p-cymene+TX, Plutella xylostella granulovirus+TX, Plutella xylostella nuclear polyhedrosis virus+TX, polyhedrosis virus+TX, pyrethrum+TX, QRD420 (terpenoid blend)+TX, QRD 452 (terpenoid blend)+TX, QRD 460 (terpenoid blend)+TX, Quillaja saponaria+TX, Rhodococcus sphaeroides AQ719 (NRRL Accession No. B-21663)+TX, Spodoptera frugiperda nuclear polyhedrosis virus+TX, Streptomyces flavos (NRRL Accession No. 30232)+TX, Streptomyces sp. (NRRL Accession No. B-30145)+TX, terpenoid blend+TX, and Verticillium sp.+TX;

[0766] an algaecide selected from the group consisting of bethoxazin [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endoxan (295) + TX, fentin (347) + TX, slaked lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) + TX, and triphenyltin hydroxide (IUPAC name) (347) + TX;

[0767] Anthelmintics selected from the group consisting of: avermectin (1) + TX, clefonate (1011) + TX, cyclopentane + TX, doramectin (alias) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alias) [CCN] + TX, ivermectin (alias) [CCN] + TX, milbemycin oxime (alias) [CCN] + TX, moxidectin (alias) [CCN] + TX, piperazine [CCN] + TX, selamectin (alias) [CCN] + TX, spinosad (737) + TX, and thiophanate (1435) + TX;

[0768] Avicides selected from the group consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) + TX, and strychnine (745) + TX;

[0769] Bactericide selected from the group consisting of: 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, dodesine (1112) + TX, fenaminosulf (1144) + TX, formaldehyde (404) + TX, mercaptophenone (IUPAC name) + TX, TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, chlorpheniramine (766) + TX, and thimerosal (other name) [CCN] + TX;

[0770] A biological agent selected from the group consisting of: GV of cotton brown banded moth (alias) (12) + TX, Agrobacterium radiobacterium (alias) (13) + TX, Amblyseius spp. (alias) (19) + TX, NPV of celery budworm (alias) (28) + TX, Anagrus atomus (alias) (29) + TX, Aphelinus abdominalis (alias) (33) + TX, Aphidius colemani (alias) (34) + TX, Aphidoletes aphidimyza (alias) (35) + TX, NPV of lucerne budworm (alias) (38) + TX, Bacillus firmus (alias) (48) + TX, Bacillus sphaericus Neide)(scientific name)(49)+TX、Bacillus thuringiensis Berliner)(scientific name)(51)+TX、Bacillus thuringiensis subsp.aizawai)(scientific name)(51)+TX、Bacillus thuringiensis subsp.israelensis)(scientific name)(51)+TX、Bacillus thuringiensis subsp.japonensis)(scientific name)(51)+TX、Bacillus thuringiensis subsp.kurstaki)(scientific name)(51)+TX、Bacillus thuringiensis subsp.tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alias) (53) + TX, Beauveria brongniartii (alias) (54) + TX, Chrysoperla carnea (alias) (151) + TX, Cryptolaemus montrouzieri (alias) (178) + TX, Codling moth GV (alias) (191) + TX, Dacnusa sibirica (alias) (212) + TX, Diglyphus isaea (alias) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus) (alias) (300) + TX, Spodoptera exigua NPV (alias) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alias) (433) + TX, Hippodamia convergens (alias) (442) + TX, Leptomastix dactylopii (alias) (488) + TX, Macrolophus caliginosus (alias) (491) + TX, Spodoptera exigua NPV (alias) (494) + TX, Metaphycus helvolus (alias) (522) + TX, Metarhizium anisopliae var.acridum)(scientific name)(523)+TX, Metarhizium anisopliae var.anisopliae)(scientific name)(523)+TX, Neodiprionsertifer NPV and Neodiprionsertifer rubrum (N.lecontei)NPV (alias) (575) + TX, Paecilomyces spp. (alias) (596) + TX, Paecilomyces fumosoroseus (alias) (613) + TX, Phytoseiulus persimilis (alias) (644) + TX, Spodopteraexigua multicapsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (alias) (742) + TX, Steinernema carpocapsae (alias) (742) + TX, Steinernema glaseri (alias) (742) + TX, Steinernema riobrave) (alias) (742) + TX, Steinernema riobravis (alias) (742) + TX, Steinernema scapterisci (alias) (742) + TX, Steinernema spp. (alias) (742) + TX, Trichogramma spp. (alias) (826) + TX, Typhlodromus occidentalis (alias) (844) + TX, and Verticillium lecanii (alias) (848) + TX;

[0771] Soil disinfectants selected from the group consisting of iodomethane (IUPAC name) (542) + TX, and bromomethane (537) + TX;

[0772] A chemical sterilant selected from the group consisting of: apholanate [CCN] + TX, bis(aziridine) methylaminophosphine sulfide (bisazir) (alias) [CCN] + TX, busulfan (alias) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alias) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, metepa [CCN] + TX, Methiotepa [CCN] + TX, methylapholate [CCN] + TX, morzid [CCN] + TX, penfluron [CCN] + TX, tepa [CCN] + TX, thiohempa [CCN] + TX, thiotepa [CCN] + TX, trothamide [CCN] + TX, and urethaneimide [CCN] + TX;

[0773] An insect pheromone selected from the group consisting of (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol (IUPAC name) (222) + TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285) + TX, (Z)-hexadecan-11-enal (IUPAC name) (436) + TX, (Z)-hexadecan-11-en-1-yl acetate (IUPAC name) (437) + TX X, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438) + TX, (Z)-eicos-13-en-10-one (IUPAC name) (448) + TX, (Z)-tetradec-7-en-1-al (IUPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783) + TX, (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784) + TX, (7E,9Z)-dodec-7,9-dien-1-yl acetate (IUPAC name) (283) + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9Z,12E)-tetradec-9,12-Dien-1-yl acetate (IUPAC name) (781) + TX, 14-methyloctadec-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one (IUPAC name) (544) + TX, alpha-multistriatin (alias) [CCN] + TX, western pine beetle gathering pheromone (brevicomin) (alias) [CCN] + TX, codlelure (alias) [CCN] + TX, codlemone (alias) (167) + TX, cuelure (alias) ( 179)+TX, disparlure (277)+TX, dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate (IUPAC name) (287)+TX, dodec-8+TX, 10-dien-1-yl acetate (IUPAC name) (284)+TX, dominicalure (alias) [CCN]+TX, ethyl 4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alias) [CCN]+TX, southern pine beetle aggregation pheromone (frontalin) (alias) [CCN]+TX, (Alternative name; a 1:1 mixture of (Z,E) and (Z,Z) isomers of hexadeca-7,11-dien-1-yl acetate) (420) + TX, grandlure (421) + TX, grandlure I (alternative name) (421) + TX, grandlure II (alternative name) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [ CCN]+TX, ipsenol (alias) [CCN]+TX, japonilure (alias) (481)+TX, lineatin (alias) [CCN]+TX, litlure (alias) [CCN]+TX, looplure (alias) [CCN]+TX, medlure [CCN]+TX, (3E,5Z)-tetradec-3,5-dienoic acid (megatomoic acid) (alias) [CCN]+TX, methyl Eugenol (alternative name) (540) + TX, muscalure (563) + TX, octadecane-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, octadecane-3,13-dien-1-yl acetate (IUPAC name) (589) + TX, orfralure (alternative name) [CCN] + TX, oryctalure (alternative name) (317) + TX, ostramone (alternative name) [CCN] + TX, siglure [CCN] + TX , banana bulb weevil attractant (sordidin) (alias) (736) + TX, sulcatol (alias) [CCN] + TX, tetradec-11-en-1-yl acetate (IUPAC name) (785) + TX, Mediterranean fruit fly attractant (839) + TX, Mediterranean fruit fly attractant A (alias) (839) + TX, Mediterranean fruit fly attractant B1 (alias) (839) + TX, Mediterranean fruit fly attractant B2 (alias) (839) + TX, Mediterranean fruit fly attractant C (alias) (839) TX, and trunc-call (alias) [CCN] + TX;

[0774] An insect repellent selected from the group consisting of 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, DEET [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexylurea [CCN] + TX, methoquin-butyl (1276) + TX, methyl neodecylamide [CCN] + TX, oxamate [CCN] + TX, and picaridin [CCN] + TX;

[0775] Molluscicide selected from the group consisting of: di(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, chloranil (999) + TX, copper acetyl arsenite [CCN] + TX, copper sulfate (172) + TX, triphenyltin (347) + TX, iron phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-ethanolamine (576) + TX, pentachlorophenol (62 3) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, trifenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) + TX, triphenyltin hydroxide (IUPAC name) (347) + TX, and pyriprole [394730-71-3] + TX;

[0776] A nematicide selected from the group consisting of: AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC / Chemical Abstracts name) (1045) + TX, 1,2-dichloropropane (IUPAC / Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane and 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC / Chemical Abstracts name) Abstract name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazin-3-yl acetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alias) (210) + TX, avermectin (1) + TX, acetofenamide [CCN] + TX, cotton bell carb (15) + TX, aldicarb (16) + TX, aldicarb (863) + TX, AZ 60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alias) + TX, chlorpyrifos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbofuran (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, Wei (999) + TX, cyclobutaflutol + TX, cytokinin (alias) (210) + TX, dazomethane (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, dimethoate (1051) + TX, dicliphos (alias) + TX, dimethoate (262) + TX, doramectin (alias) [ CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin (alias) [CCN]+TX, ethoprophos (312)+TX, dibromoethane (316)+TX, fenamiphos (326)+TX, fenpyrad (alias)+TX, fensulfuron (1158)+TX, thiazophos (408)+TX, butasulfophos (1196)+TX, furfural Aldehyde (alias) [CCN] + TX, GY-81 (research code) (423) + TX, cypermethrin [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, chlorfenapyr (1231) + TX, ivermectin (alias) [CCN] + TX, kinetin (alias) (210) + TX, methyl aphidoxime (1258) + TX,Metamex (519) + TX, Metamex potassium salt (alias) (519) + TX, Metamex sodium salt (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, Milbemycin oxime (alias) [CCN] + TX, Moxidectin (alias) [CCN] + TX, Myrothecium verrucaria composition (alias) (565) + TX, NC-184 (compound code) + TX, Oxamyl (602) + TX, Phorate (636) + TX, Phosphamidon (639) + TX, Phosphamidon [CCN] + TX, Clematin (alias) + TX, Selamectin (alias) [C CN]+TX, spinosad (737)+TX, terbufos (alias)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC / Chemical Abstracts name) (1422)+TX, thiafenox (alias)+TX, cypermethrin (1434)+TX, triazophos (820)+TX, triazuron (alias)+TX, dimethylol [CCN]+TX, YI-5302 (compound code)+TX, zeatin (alias) (210)+TX, fluensulfone [318290-98-1]+TX, and fluopyram+TX;

[0777] A nitrification inhibitor selected from the group consisting of potassium ethylxanthate [CCN] + TX, and nitrapyrin (580) + TX;

[0778] A plant activator selected from the group consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) + TX, and Reynoutria sachalinensis extract (alias) (720) + TX;

[0779] Rodenticide selected from the group consisting of: 2-isovaleryl indan-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, α-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, antoquinol (880) + TX, arsenic trioxide (882) + TX, barium carbonate (891) + TX, bisulfamethoxazole (912) + TX, brodifacoum (89) + TX, bromadiolone (including α-Bromadiolone) + TX, Bromadiolamine (92) + TX, Calcium Cyanide (444) + TX, Chloralose (127) + TX, Chloralone (140) + TX, Cholecalciferol (alias) (850) + TX, Chlorodiol (1004) + TX, Cyclodextrin (1005) + TX, Cyclodextrin (175) + TX, Cyclodextrin (1009) + TX, Cyclodextrin (246) + TX, Cyclodextrin (249) + TX, Cyclodextrin (273) + TX, Calciferol (301) + TX, Fluorodiol Fluorothiazolin (357) + TX, fluoroacetamide (379) + TX, fluridine (1183) + TX, fluridine hydrochloride (1183) + TX, γ-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (IUPAC name) (640) + TX, methyl bromide (537) + TX, thiamethoxam (1318) + TX, thiamethoxam (1336) + TX )+TX, phosphine (IUPAC name) (640)+TX, phosphorus [CCN]+TX, warfarin (1341)+TX, potassium arsenite [CCN]+TX, warfarin (1371)+TX, scilla glycoside (1390)+TX, sodium arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX, strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851)+TX, and zinc phosphide (640)+TX;

[0780] Synergist selected from the group consisting of: 2-(2-butoxyethoxy)ethyl piperonate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol with nerolidol (alias) (324) + TX, MB-599 (research code) (498) + TX, MGK 264 (research code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl ester ( isomer)(1358)+TX, S421 (research code) (724)+TX, sesamex (1393)+TX, sesasmolin (1394)+TX, and sulfoxide (1406)+TX;

[0781] Animal repellents selected from the group consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper cyclohexane [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetate (422) + TX, methiocarb (530) + TX, pyridin-4-amine (IUPAC name) (23) + TX, salamine (804) + TX, trimethacarb (840) + TX, zinc cyclohexane [CCN] + TX, and ziram (856) + TX;

[0782] A virucidal agent selected from the group consisting of: imamin (also known as CCN) and ribavirin (also known as CCN) + TX;

[0783] A wound protection agent selected from the group consisting of mercuric oxide (512) + TX, octhilinone (590) + TX, and thiophanate-methyl (802) + TX;

[0784] Biologically active substances selected from 1,1-bis(4-chloro-phenyl)-2-ethoxyethanol+TX, 2,4-dichlorophenylbenzenesulfonate+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide+TX, 4-chlorophenylphenylsulfone+TX, acetofenapyr+TX, aldisulfonyl+TX, sagofos+TX, fomanphos+TX, amitriptyline+TX, amitriptyline hydrogen oxalate+TX, amitraz+TX, cypermethrin+TX, arsenic trioxide+TX, azobenzene+TX, azophos+TX, benomyl+TX, benoxaphos+TX, benzyl benzoate+TX, bixafenthion+TX, bromothiophene+TX, bromothiophene+TX, bromothiophene+TX X, bromopyralid + TX, buprofezin + TX, butanone carbendazim + TX, butanone carbendazim + TX, butylpyridaben + TX, calcium polysulfide + TX, octachlorocamphene + TX, chlormethoxam + TX, trithion + TX, cypermethrin + TX, cypermethrin + TX, cypermethrin + TX, chlordimeform + TX, chlordimeform hydrochloride + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, ethyl chlorfenapyr + TX, chlorfenapyr + TX, propyl chlorfenapyr + TX, chlorfenapyr + TX, cypermethrin I + TX, cypermethrin II + TX, cypermethrin + TX, closantel + TX, coumaphos + TX, crotamiton + TX, baclofos + T X, thiophanate + TX, chlorfenapyr + TX, DCPM + TX, DDT + TX, dinapyr + TX, dinapyr-O + TX, dinapyr-S + TX, demeton-methyl + TX, demeton-O + TX, demeton-O-methyl + TX, demeton-S + TX, demeton-S-methyl + TX, demeton-S-methyl + TX, demeton-S-methyl + TX, demeton-S-methyl + TX, chlorfenapyr + TX, dichlorvos + TX, dicliphos + TX, dichlorvos + TX, dimethoate + TX, dimethoate + TX, dimethoate + TX, dinex + TX, dinex-diclexine + TX, dimethoate Pu-4+TX, diclofenac-6+TX, orthodimethoate+TX, nitropentyl+TX, nitrooctyl ester acaricide+TX, nitrobutyl+TX, dimethoate+TX, sulfodiphenyl+TX, disulfiram+TX, DNOC+TX, phenoxyacetic acid+TX, doramectin+TX, fenoxaphos+TX, eprinomectin+TX, phosphamidon+TX, ethimox+TX, anti-mite+TX, fenbutatin+TX, fenthiocarb+TX, fenpyrad+TX, fenpyraclostrobin+TX, fenamipyraclostrobin+TX, fenpyrad+TX, fluazifop+TX, flunitroaniline+TX, fluazifop+TX, flufenoxuron+TX, fluazifop+TX, FMC 1137+TX, fenvalerate+TX, fenvalerate hydrochloride+TX, carbendazim+TX, γ-HCH+TX, chlorpyrifos+TX, benzyl methoxyfen+TX, hexadecyl cyclopropane carboxylate+TX, isocarbophos+TX, jasmonate I+TX, jasmonate II+TX, iodonium sulfate+TX, lindane+TX, propanil+TX,Mefenacet + TX, dithiophos + TX, methylthiophene + TX, acarb + TX, methyl bromide + TX, methicillin + TX, chlorpyrifos + TX, milbemycin + TX, propylamine + TX, monocrotophos + TX, maoguo + TX, moxidectin + TX, dibromophos + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, fluazifop + TX, nikkomycin + TX, pentocyanamide + TX, pentocyanamide 1:1 zinc chloride complex + TX, omethoate + TX, isothiocarb + TX, sulfamethoxam + TX, pp'-DDT + TX, parathion + TX, permethrin + TX, fenthion + TX, phosalone + TX, thiophanate + TX, phosphamidon + TX, phosphamidon + TX, chlorinated turpentine + TX, acaricide + TX, proclonol + TX, cypermethrin + TX, propoxur + TX, ethidium + TX, pyrethrin + TX, pyrethrin I + TX, pyrethrin II + TX, pyrethrin + TX, pyrimethoxam + TX, pyrimithiophos + TX, quinalphos + TX, quintiofos + TX, R-1492 + TX, glyphosate + TX, rotenone + TX, octamidine + TX, clomar + TX, selamectin + TX, thiothion + TX, SSI-121 + TX, sulfluramid + TX, sulfotep + TX, sulfur + TX, fluazifop + TX, τ-fluvalinate + TX, TEPP + T X, terbucarb + TX, tetrachlorobenzene + TX, acarbicide + TX, thiafenox + TX, pyrimidine + TX, long-lasting chlorpyrifos + TX, methyl benzylphos + TX, chlorpyrifos + TX, thiamethoxam + TX, thiamethoxam + TX, triazophos + TX, chlorpyrifos + TX, triclosan + TX, triamcinol + TX, aphidoxam + TX, methyl fipronil + TX, pyrimidine + TX, copper dioctanoate + TX, copper sulfate + TX, cybutryne + TX, dichloronaphthoquinone + TX, dichlorophen + TX, endoxan + TX, triphenyltin + TX, slaked lime + TX, sodium mancozeb + TX, chlorpyrifos + TX, quinone + TX, simazine + TX, triphenyltin acetate + TX, triphenylhydrazine Tin oxide + TX, folate + TX, piperazine + TX, thiophanate + TX, chloralose + TX, fenthion + TX, pyridin-4-amine + TX, strychnine + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 8-hydroxyquinoline sulfate + TX, bronopol + TX, copper hydroxide + TX, cresol + TX, dipyrithione + TX, dodixan + TX, sodium disulfone + TX, formaldehyde + TX, mercury + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, nickel bis(dimethyldithiocarbamate) + TX, trichloromethylpyridine + TX, octhiothione + TX, oxolinic acid + TX, oxytetracycline + TX, potassium hydroxyquinoline sulfate + TX,Thiabendazole+TX, Streptomycin+TX, Streptomycin sesquisulfate+TX, Chlorophyll+TX, Thimerosal+TX, GV of the cotton brown-banded tormentor+TX, Agrobacterium radiobacterium+TX, Amblyseius species+TX, Spodoptera exigua NPV+TX, Procera ceranae+TX, Aphididae short-spurred wasp+TX, Cotton aphid parasitoid wasp+TX, Aphid midge+TX, Spodoptera lucerne NPV+TX, Bacillus sphaericus+TX, Beauveria bassiana+TX, Common lacewing+TX, Cryptochilus mandshurica+TX, GV of the codling moth+TX, Siberian sibirica+TX, Pea leafminer+TX, Aphididae ensifolia+TX , Aphididae + TX, Bacteriotrophic Heterorhabditis elegans and Heterorhabditis elegans + TX, Spotted Long-legged Ladybird + TX, Scale Parasitoid Wasp + TX, Misty Bug + TX, Cabbage Lobelia NPV + TX, Yellow-stalked Jumping Lobelia + TX, Yellow-green Metarhizium + TX, Metarhizium anisopliae Microspore Var. + TX, New European Pine Sawfly NPV and New Red-headed Pine Sawfly NPV + TX, Small Flower Bug Species + TX, Fumosomolus Roseus + TX, Chilean Small Plant Mite + TX, Hairy Mosquito Nematode + TX, Small Rolled Moth Nematode + TX, Noctuid Moth Nematode + TX, Grill's Nematode + TX, Steinernema sharpiena + TX, Steinernema riobravis+TX, mole cricket Steinernema+TX, Steinernema species+TX, Trichogramma species+TX, western blind mite+TX, Verticillium lecanii+TX, zophosphine+TX, bis(aziridine)methylaminophosphonium sulfide+TX, busulfan+TX, dimethivin+TX, hexamethylmelamine+TX, hexamethylphosphine+TX, methyl thiophosphine+TX, methylzophosphine+TX, infertility pyridine + TX, flubendiamide + TX, thiamethoxam + TX, thiamethoxam + TX, trothamide + TX, urethaneimine + TX, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-diene- 1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-eicos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)- Tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodec-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX,4-Methylnon-5-ol and 4-methylnon-5-one + TX, α-polystyrene + TX, western pine beetle gathering pheromone + TX, dodecadienol + TX, caldoxime + TX, tardione + TX, epoxynonadecane + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, dodec-8 + TX, 10-dien-1-yl acetate + TX, dominicalure + TX, ethyl 4-methyloctanoate + TX, eugenol + TX, southern pine beetle gathering pheromone + TX, tardione mixture + TX, tardione mixture I + TX, tardione mixture II + TX, tardione mixture III + TX, tardione mixture IV + TX, hexane + TX, tooth beetle dienol + TX, beetle beetle sex attractant + TX, trimethyldioxytricyclononane + TX, litlure + TX, cabbage looper sex attractant + TX, trapping ester + TX, (3E,5Z)-tetradec-3,5-dienoic acid + TX, trapping ether + TX, trapping ene + TX, octadec-2,13-dien-1-yl acetate + TX, octadec-3,13-dien-1-yl acetate + TX, Hekangbi + TX, coconut rhinoceros beetle aggregation pheromone + TX, non-lecon + TX, trapping ring + TX, sordidin + TX, fungivorous acetic acid + TX, tetradec-11-en-1-yl acetate + TX, Mediterranean fruit fly attractant + TX, Mediterranean fruit fly attractant Attractant A+TX, Mediterranean fruit fly attractant B1+TX, Mediterranean fruit fly attractant B2+TX, Mediterranean fruit fly attractant C+TX, trunc-call+TX, 2-(octylthio)ethanol+TX, dimethoate+TX, butoxy(polypropylene glycol)+TX, dibutyl adipate+TX, dibutyl phthalate+TX, dibutyl succinate+TX, DEET+TX, mosquito repellent+TX, dimethyl phthalate+TX, ethyl hexanediol+TX, hexyl urea+TX, mequindine+TX, methyl neodecylamide+TX, oxamate+TX, picaridin+TX, 1-dichloro-1-nitroethane+TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)-ethane+TX, 1, 2-Dichloropropane and 1,3-dichloropropylene + TX, 1-bromo-2-chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenylmethylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolidinone + TX, 2-isovalerylindan-1,3-dione + TX,2-Methyl (prop-2-ynyl) aminophenyl methylcarbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yl dimethyl-carbamate + TX, 4-methyl (prop-2-ynyl) amino-3,5-dimethylphenyl methylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate + TX, acethion + TX, acrylonitrile + TX, aldrin + TX, aloamicin + TX, chlorpyrifos + TX, α-decadin + TX, aluminum phosphide + TX, chlorpyrifos + TX, neonicotinoid + TX, ethyl methidathion + TX, methyl pyrifos + TX, Bacillus thuringiensis δ-endotoxin + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, cypermethrin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, β-cyfluthrin + TX, β-cypermethrin + TX, pentocyclam + TX, biopermethrin + TX, bis(2-chloroethyl) ether + TX, borax + TX, bromophenirone + TX, bromo-DDT + TX, cypermethrin + TX, cyfluthrin + TX, temirphos + TX, butyl phosphate + TX, calcium arsenate + TX, calcium cyanide + TX, carbon disulfide + TX, carbon tetrachloride + TX, cypermethrin hydrochloride + TX, servadine + TX, bornyl + TX, chlordane + TX, chlordecone + TX, chloroform + TX, chloropicrin + TX, chloranisole + TX, chlorpyrifos + TX, cis-resmethrin + TX, cis-resmethrin + TX, cypermethrin + TX, copper acetylarensite + TX, copper arsenate + TX, copper oleate + TX, cypermethrin + TX, cryolite + TX, CS 708+TX, benzonitrile+TX, cypermethrin+TX, cypermethrin+TX, cypermethrin+TX, d-cypermethrin+TX, DAEP+TX, dazomethon+TX, demethylcarbofuran+TX, chloranil+TX, isochlorvinphos+TX, chloranil+TX, dicresyl+TX, cypermethrin+TX, dieldrin+TX, diethyl 5-methylpyrazol-3-yl phosphate+TX, thiophene+TX, tetrafluthrin+TX, demacarb+TX, pyrethrin+TX, methylchlorfenapyr+TX, difenocarb+TX, propanol+TX, pentotropol+TX, dinoseb+TX, fenpropathrin+TX, vegetable phosphorus+TX, thiopyraphos+TX, DSP+TX, ecdysterone+TX, EI 1642+TX, EMPC+TX, EPBP+TX, etaphos+TX, ethiobencarb+TX, ethyl formate+TX, dibromoethane+TX, dichloroethane+TX, ethylene oxide+TX, EXD+TX, ethiobencarb+TX, ethiobencarb+TX, fenitrothion+TX, pyrimidine+TX, cypermethrin+TX, fenthion+TX, ethylfenthion+TX, chlorpyrifos+TX, butylfenthion+TX, phosphamidon+TX,Butylthion + TX, Fusalcarb + TX, Pyrethroid + TX, Biguanidine salt + TX, Biguanidine acetate + TX, Sodium tetrathiocarbonate + TX, Benzofen + TX, HCH + TX, HEOD + TX, Heptachlor + TX, Methiothion + TX, HHDN + TX, Hydrogen cyanide + TX, Quinoline + TX, IPSP + TX, Cyclofos + TX, Carbochlorin + TX, Isoaldrin + TX, Isothiophos + TX, Transplanting agent + TX, Blasticide + T X, oxazophos + TX, juvenile hormone I + TX, juvenile hormone II + TX, juvenile hormone III + TX, chlorpentyl + TX, methoprene + TX, lead arsenate + TX, bromophenophos + TX, pyralidon + TX, thiazophos + TX, m-isopropyl methylcarbamate + TX, magnesium phosphide + TX, phosphorus azide + TX, methyl azoxyphos + TX, thiamethoxam + TX, mercurous chloride + TX, methyl sulfoxide + TX, metamifene + TX, metamifene potassium salt +TX, sodium salt of Metamex +TX, methylsulfonyl fluoride +TX, butenamidophos +TX, methoprene +TX, methylthiothrin +TX, methoxychlor +TX, methyl isothiocyanate +TX, methyl chloroform +TX, dichloromethane +TX, oxadiazine +TX, mirex +TX, napeptide +TX, naphthalene +TX, NC-170 +TX, nicotine +TX, nicotine sulfate +TX, nithiazine +TX, pronicotine +TX, O-5-dichloro-4-iodo Phenyl O-ethyl ethyl phosphonothioate + TX, O,O-diethyl O-4-methyl-2-oxo-2H-benzopyran-7-yl phosphonothioate + TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphonothioate + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate + TX, oleic acid + TX, p-dichlorobenzene + TX, methyl parathion + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, PH 60-38+TX, fenthion+TX, parachlorothion+TX, phosphine+TX, methyl phoxim+TX, methamidophos+TX, polychlorinated dicyclopentadiene isomers+TX, potassium arsenite+TX, potassium thiocyanate+TX, precocious plant I+TX, precocious plant II+TX, precocious plant III+TX, amidopyrimidin+TX, fluthrin+TX, fenvalerate+TX, prothiophos+TX, pyraclostrobin+TX, anti-pyrethroid+TX, quassia extract+TX, quinalphos-methyl+TX, fenvalerate+TX, iodophos+TX, Resmethrin + TX, Rotenone + TX, Thiamphenicol + TX, Ronitin + TX, Rianodin + TX, Veratrum sabalii + TX, Phosphate + TX, Clamine + TX, SI-0009 + TX, Thiaclonitrile + TX, Sodium arsenite + TX, Sodium cyanide + TX, Sodium fluoride + TX, Sodium hexafluorosilicate + TX, Sodium pentachlorophenol + TX, Sodium selenate + TX, Sodium thiocyanate + TX, Sulfonamide + TX, Sulfonamide sodium salt + TX, Sulfuryl fluoride + TX, Thiaprophos + TX, Tar + TX, Thiamethoxam + TX, TDE + TX,Butylpyrimidinphos + TX, bispyribac + TX, cypermethrin + TX, tetrachloroethane + TX, thiochlorvos + TX, cyclohexane + TX, cyclohexane oxalate + TX, cypermethrin + TX, cypermethrin sodium + TX, tralomethrin + TX, permethrin + TX, triazolam + TX, isothiocyanate + TX, chlorpyrifos + TX, cyclohexanone + TX, trifloxystrobin + TX, chlorpyrifos + TX, chlorpyrifos + TX, trifloxystrobin + TX, chlorpyrifos + TX, chlorpyrifos + TX, veratridine + TX, veratridine + TX, XMC + TX, zetamethrin + TX, zinc phosphide + TX, tolfenphos + TX, chlorfluanid + TX X, tetrafluthrin + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, ferric phosphate + TX, niclosamide-ethanolamine + TX, tributyltin oxide + TX, pyromorph + TX, snail killer + TX, 1,2-dibromo-3-chloropropane + TX, 1,3-dichloropropylene + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6-thioxo-1,3,5-thiadiazin-3-yl acetic acid + TX, 6-isopentenylaminopurine + TX, anisiflupurin + TX, benzochlorothiazide +TX, cytokinin +TX, DCIP +TX, furfural +TX, isoamidophos +TX, kinetin +TX, verrucous myristic fungus composition +TX, tetrachlorothiophene +TX, xylenol +TX, zeatin +TX, potassium ethylxanthate +TX, acibenzolar +TX, acibenzolar-S-methyl +TX, giant knotweed extract +TX, α-chlorohydrin +TX, anto +TX, barium carbonate +TX, bismuth urea +TX, brodifacoum +TX, bromadiolone +TX, bromodiolone +TX, chlordicarb +TX, cholecalciferol +TX, chlorfenapyr +TX, chlorambucil +TX, chloramphenicol +TX, chlorambucil +TX, chloramphenicol +TX, Pyridine + TX, Felodipine + TX, Thiazide + TX, Diphacin + TX, Calciferol + TX, Fludioxaline + TX, Fluacetamide + TX, Fludioxaline + TX, Fludioxaline hydrochloride + TX, Felodipine + TX, Felodipine + TX, Felodipine + TX, Phosphate + TX, Phosphate + TX, Felodipine + TX, Felodipine + TX, Felodipine + TX, Felodipine + TX, Felodipine glycoside + TX, Sodium fluoroacetate + TX, Thallium sulfate + TX, Felodipine + TX, 2-(2-butoxyethoxy)ethyl piperate + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, Farnesol with nerolidol + TX, Synergistic alkynyl ether + TX, MGK 264+TX, piperonyl butoxide+TX, synergistic aldehyde+TX, propyl isomer+TX, S421+TX, synergistic powder+TX, sesame linolenic acid+TX, sulfoxide+TX, anthraquinone+TX, copper naphthenate+TX, copper oxychloride+TX, dicyclopentadiene+TX, ceram+TX, zinc naphthenate+TX, ziram+TX, imanin+TX, ribavirin+TX, chloroinconazide+TX, mercuric oxide+TX,Thiophanate methyl + TX, azaconazole + TX, bifenthiazolin + TX, oxadiazol + TX, cyproconazole + TX, difenoconazole + TX, diniconazole + TX, epoxiconazole + TX, fenbuconazole + TX, fluquinconazole + TX, flusilazole + TX, flutriafol + TX, furazolidone + TX, hexaconazole + TX, imazalil + TX, imidazole + TX, picronil + TX, metconazole + TX, myclobutrazol + TX, paclobutrazol + TX, blastifungin + TX, penconazole + TX, prothioconazole + TX, pyraclostrobin + TX, prochloraz + TX, propiconazole + TX, pyraclostrobin + TX, silyfenazole + TX, tebuconazole + TX, fluconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, triticonazole + TX, pyrimidine Alcohol + TX, chlorfenapyr + TX, flufenapyr + TX, pyrimidine sulfonate + TX, mefenamic acid + TX, mefenamic acid + TX, dodecacyclic morpholine + TX, fenpropidin + TX, fenpropimorph + TX, spiroxafil + TX, tridemorph + TX, cyprodinil + TX, myxazinamide + TX, myxazinamide + TX, fenpiclonil + TX, fludioxonil + TX, bensulfuron + TX, furalaxyl + TX, metalaxyl + TX, R-metalaxyl + TX, furamide + TX, oxadixyl + TX, carbendazim + TX, imidacloprid + TX, maixin + TX, thiabendazole + TX, mefenamic acid + TX, sclerotinol + TX, mefenamic acid + TX, procymidone + TX, vinclozolin + TX, boscalid + TX, carboxin + TX, mefenamic acid Furoxamide + TX, Flutolanil + TX, Mefenamic Acid + TX, Oxycarboxin + TX, Penthiopyrad + TX, Thifuranil + TX, Dodine + TX, Biguanide + TX, Azoxystrobin + TX, Dioxastrobin + TX, Enstrobin + TX, Enstrobin + TX, Fluoxastrobin + TX, Dioxastrobin + TX, Dioxastrobin + TX, Dioxastrobin + TX, Dioxastrobin + TX, Dioxastrobin + TX, Picoxystrobin + TX, Pyraclostrobin + TX, Pyraclostrobin + TX, Pyraclostrobin + TX, Ferram + TX, Mancozeb + TX, Maneb + ​​TX, Maneb + ​​TX, Metiram + TX, Methionine + TX, Maneb + ​​TX, Maneb + ​​TX, Captafol + TX, Captan + TX, Fentan + TX, Folpet + TX, Tolylfluanid + TX , Bordeaux mixture + TX, copper oxide + TX, mancozeb + TX, quinoline copper + TX, phthalocyanine + TX, kewensan + TX, isoprene + TX, chlorpyrifos + TX, tolclofos-methyl + TX, difop-butyl + TX, benzathiapiprolin + TX, blasticidin-S + TX, dimethoate + TX, chlorothalonil + TX, cyfluanid + TX, cymoxanil + TX, cyclobutrifluram + TX, dichlorocyanamide + TX, pyraclostrobin + TX, chloranil + TX, ethofluanid + TX, dimethomorph + TX, flumorph + TX, dithianon + TX, ethidiumb + TX, oxadone + TX, famoxadone + TX, imidacloprid + TX, blastic amide + TX, pyrimidine + TX, fluazinam + TX,flumetylsulforim+TX, fluopyram+TX, fluoxytioconazole+TX, sulfaquinoxaline+TX, flupyrosinone+TX, fenhexamid+TX, fosetyl-aluminum+TX, oxamexazole+TX, propineb+TX, saizoline+TX, sulfaquinoxaline+TX, mefenoxam+TX, pencycuron+TX, phthalide+TX, polyoxin+TX, propamocarb+TX, pyraclostrobin+TX, iodoquinoxaline+TX, pyroquilon+TX, fenpyrad+TX, quinoxyfen+TX, pentachloronitrobenzene+TX, thiazolinone+TX, imidazolinone+TX, tricyclazole+TX, triamcinol+TX, validamycin+TX, valosin+TX, zoxamide+TX, dimethoate Flupyrad + TX, flubeneteram + TX, pyraclostrobin + TX, flutoxazolin + TX, benzovinflupyrad + TX, flutoxazolin hydroxylamine + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, isoflurane + TX, isoflucypram + TX, dithiazolin + TX, dipymetitrone + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithia[1,2-c]isothiazole-3-carbonitrile + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3 -formamide + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, fluindapyr + TX, Jiaxiangjunzhi + TX, lvbenmixianan + TX, dichlorothiocarbamate ( dichlobentiazox) + TX, Mandespin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolinyl)oxy]phenyl]propan-2-ol + TX, thiophene + TX, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamic acid tert-butyl ester + TX, pyraziflumid + TX, inpyrfluxam + TX, trolprocarb + TX, chlorfluanidazole + TX, ipfentrifluconazole + TX,2-(Difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazole oxazol-5-yl]-3-chloro-phenyl] methanesulfonate + TX, N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamic acid but-3-ynyl ester + TX, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamic acid methyl ester + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridachlometyl + TX, 3-(difluoromethyl)-1-methyl-N -[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide+TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one+TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one+TX, aminopyrifen+TX, pyraclostrobin+TX, indazolesulfamyl+TX, fluopicolide+TX, (Z,2E)-5-[1-(4 -chlorophenyl) pyrazol-3-yl] oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine + TX, florylpicoxamid + TX, benzylpicoxamid + TX, metarylpicoxamid + TX, isobutylethoxyquinoline + TX, ipflufenoquin + TX, quinofumelin + TX, isopropylthiopyrad + TX, 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane-2-yl] methoxy] phenyl] methyl] pyrazole-3-carboxylic acid ethyl ester + TX (can be made from WO 2020 / 056090), 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enyloxy]phenyl]methyl]pyrazole-3-carboxylic acid ethyl ester + TX (can be prepared by the method described in WO 2020 / 056090), N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamic acid methyl ester + TX (can be prepared by the method described in WO 2020 / 097012),Methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate + TX (can be prepared by the method described in WO 2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide + TX (can be prepared by the method described in WO 2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide + TX (can be prepared by the method described in WO 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide+TX (can be prepared by the method described in WO 2020 / 109391), N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide+TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide+TX, thiocyanatoxin+TX, cyproconazole+TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt ( 2:1)+TX, fluopyram+TX, flufenoxadiazam+TX, fluthiazolinone+TX, fluopyram+TX, pyrapropoyne+TX, piperacodazole+TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide+TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3- Formamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, metyltetraprole + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, α-(1,1-dimethylethyl)-α-[4'- (Trifluoromethoxy) [1,1'-diphenyl] -4-yl] -5-pyrimidinemethanol + TX, fluoxapiprolin + TX, enoxastrobin + TX, (Z) -3-methoxy-2- [2-methyl-5- [4- (trifluoromethyl) triazol-2-yl] phenoxy] prop-2-enoic acid methyl ester + TX, (Z) -3-methoxy-2- [2-methyl-5- (4-propyltriazol-2-yl) phenoxy] prop-2-enoic acid methyl ester + TX,(Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoic acid methyl ester + TX (these compounds can be prepared by the method described in WO2020 / 079111), (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester + TX, (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester + TX (these compounds can be prepared by the method described in WO2020 / 079111), 2020 / 193387), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4- 1-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, trinexapac-ethyl + TX, syringostaryl + TX, zhongshengmycin + TX, thiophanate-methyl + TX, thiazole zinc + TX, amectotractin + TX, iprodione + TX, seboctylamine + TX; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX,N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared by WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared by the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared by the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX (these compounds can be prepared by WO 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1 -benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX,N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX (these compounds can be prepared by the method described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3 ,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline+TX,4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline+TX,1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline+T X (these compounds can be prepared by the method described in WO2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + TX (these compounds can be prepared by the method described in WO2017 / 025510); 2016 / 156085); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide+TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide+TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide+TX, 1-methoxy-3-methyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea+TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea+TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea+TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide+TX,4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one+TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one+TX, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester+TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine+TX. The compounds in this paragraph can be prepared by WO 2017 / 055473, WO 2017 / 055469,Prepared by the method described in WO 2017 / 093348 and WO 2017 / 118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol+TX (this compound can be prepared by the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol+TX (this compound can be prepared by the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile+TX (this compound can be prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (this compound can be prepared by the method described in WO 2016 / 156290); 2-amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxyphenyl) methyl ester + TX (this compound can be prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']bipyrrole-1,3,5,7(2H,6H)-tetraone + TX (this compound can be prepared by the method described in WO2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine + TX (this compound can be prepared by the method described in WO2011 / 138281); 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared by the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX (this compound can be prepared by the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX,(3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone+TX (these compounds can be prepared by the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide+TX (this compound can be prepared by the method described in WO 2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester+TX (this compound can be prepared by the method described in WO 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide+TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX, N-[N-methoxy-C-methyl-carbonimido]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX (these compounds can be prepared by the method described in WO 2018 / 202428);

[0785] Microorganisms, including: Acinetobacter lwoffii + TX, Acremonium + TX + TX, Cephalosporium acremonium + TX + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, and AdoxGV Agrobacterium radioactive strain K84 Alternaria + TX, Alternaria cassiae + TX, Alternaria destruens Parasitoid spores Aspergillus flavus AF36 Aspergillus flavus NRRL 21882 Aspergillus species + TX, Aureobasidium pullulans + TX, Azospirillum Azotobacter + TX, Azotobacter chroocuccum Azotobacter cysts Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinosporus strain CM-1 + TX, Bacillus chitinosporus strain AQ746 + TX, Bacillus licheniformis strain HB-2 (e.g. Biostart TM ,Before )+TX, Bacillus licheniformis strain 3086 Bacillus circulans + TX, Bacillus firmus Bacillus firmus strain I-1582 + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycoides strain AQ726 + TX, Bacillus lactis Bacillus pumilus species + TX, Bacillus pumilus strain GB34 Bacillus pumilus strain AQ717+TX, Bacillus pumilus strain QST 2808 Bacillus spahericus Bacillus species + TX, Bacillus strain AQ175 + TX, Bacillus strain AQ177 + TX, Bacillus strain AQ178 + TX, Bacillus subtilis strain QST 713 Bacillus subtilis strain QST714 Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis amyloliquefaciens variant strain FZB24 Bacillus thuringiensis Cry 2Ae+TX, Bacillus thuringiensis Cry1Ab+TX, Bacillus thuringiensis aizawai GC 91 Bacillus thuringiensis israelensis Bacillus thuringiensis kurstaki Bacillus thuringiensis kurstaki BMP 123 Bacillus thuringiensis subsp. Kurstaki HD-1 Bacillus thuringiensis strain BD#32+TX, Bacillus thuringiensis strain AQ52+TX, Bacillus thuringiensis var. aizawai Bacterial species Bacteriophage of Clavipacter michiganensis Beauveria bassiana Beauveria bassiana GHA Beauveria brongniartii Beauveria spp. + TX, Botrytiscineria + TX, Bradyrhizobium japonicum Brevibacillus brevis + TX, Bacillus thuringiensis tenebrionis BtBooster+TX, Burkholderia cepacia Burkholderiagladii+TX, Burkholderia gladioli+TX, Burkholderia spp.+TX, Canadian thistle fungus Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida elebiosica + TX, Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reukaufii + TX, Candida saitoana Candida sake + TX, Candida species + TX, Candida tenius + TX, Cedecea dravisae + TX, Cellulomonas flavigena + TX, Chaetomium cochliodes Chaetomium globosum Chromobacterium subtsugae strain PRAA4-1T Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium chlorocephalum + TX, Cladosporium spp. + TX, Cladosporium tenuissimum + TX, Clonostachys rosea Colletotrichum cutatum+TX, Coniothyrium minitans Coniothyrium spp. + TX, Cryptococcus albidus Cryptococcus humicola + TX, Cryptococcus infirmo-miniatus + TX, Cryptococcus laurentii + TX, Cryptophlebia leucotreta granulovirus Cupriavidus campinensis + TX, Cydia pomonella granulovirus Cydia pomonella granulovirus Cylindrobasidium laeve Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum spp. + TX, Filobasidium floriforme + TX, Fusarium umaminasium + TX, Fusarium chlamydosporum + TX, Fusarium oxysporum Fusarium proliferatum + TX, Fusarium spp. + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum Gliocladium roseum + TX, Gliocladium spp. Gliocladium virens Granulovirus Halobacillus halophilus + TX, Halobacillus litoralis + TX, Halobacillus trueperi + TX, Halomonas spp. + TX, Halomonas subglaciescola + TX, Halovibrio variabilis + TX, Hanseniaspora uvarum + TX, Helicoverpa armigera nucleopolyhedrovirus Helicoverpa zea nuclear polyhedrosis virus Isoflavone-formononetin Kloeckera apiculata + TX, Kloeckera spp. + TX, Lagenidium giganteum Lecanicillium longisporum Lecanicillium muscarium Lymantria Disparnucleopolyhedrosis virus Marinococcus halophilus + TX, Meira geulakonigii + TX, Metarhizium anisopliae Metarhizium anisopliae Metschnikowia fruticola Maggi yeast (Metschnikowiapulcherrima) + TX, (Microdochium dimerum) Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 Muscodor roseus strain A3-5+TX, Mycorrhizae spp. Myrothecium verrucaria strain AARC-0255 BROS Ophiostoma piliferum strain D97 Paecilomyces farinosus + TX, Paecilomyces fumosoroseus Paecilomyces linacinus Paecilomyces lilacinus strain 251 Paenibacillus polymyxa + TX, Pantoea agglomerans Pantoea spp. + TX, Pasteuria spp. Pasteurianishizawae+TX、Penicillium aurantiogriseum+TX、Penicillium billai Penicillium brevicompactum + TX, Penicillium frequentans + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp. + TX, Penicillium viridicatum + TX, Phlebiopsis gigantean Phosphate solubilizing bacteria Phytophthora cryptogea + TX, Phytophthora palmivora Pichia anomala + TX, Pichia guilermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofasciens Pseudomonas cepacia + TX, Pseudomonas chlororaphis Pseudomonas corrugate + TX, Pseudomonas fluorescens strain A506 Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp. + TX, Pseudomonas syringae Pseudomonas viridiflava + TX, Pseudomonas fluorescens Pseudozyma flocculosa strain PF-A22 UL Puccinia canaliculata + TX, Puccinia thlaspeos Pythium paroecandrum+TX, Pythium oligandrum Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizobia Rhizoctonia + TX, Rhodococcus globerulus strain AQ719 + TX, Rhodosporidium diobovatum + TX, Rhodosporidium toruloides + TX, Rhodotorula spp. + TX, Rhodotorula glutinis + TX, Rhodotorula graminis + TX, Rhodotorula mucilagnosa + TX, Rhodotorula rubra + TX, Saccharomyces cerevisiae + TX, Salinococcus roseus + TX, Sclerotiniaminor + TX, Sclerotiniaminor Scytalidium spp.+TX, Scytalidium uredinicola+TX, Spodoptera exigua nuclear polyhedrosis virus Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp. + TX, Sordaria fimicola + TX, Spodoptera littoralis nuclear polyhedrovirus Sporobolomyces roseus + TX, Stenotrophomonas maltophilia + TX, Streptomyces ahygroscopicus + TX, Streptomyces albaduncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, Streptomyces griseoplanus + TX, Streptomyces griseoviridis Streptomyces lydicus Streptomyces lydicus WYEC-108 Streptomyces violaceus + TX, Tilletiopsis minor + TX, Tilletiopsis spp. + TX, Trichoderma asperellum Trichoderma gamsii Trichoderma atroviride Trichodermahamatum TH 382+TX, Trichoderma harzianum rifai Trichoderma harzianum T-22 Trichoderma harzianum T-39 Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma spp. LC 52 Trichodermalignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum Trichoderma taxi + TX, Trichoderma virens + TX, Trichoderma virens (formerly known as Gliocladium virens GL-21) Trichoderma viride + TX, Trichoderma viride strain ICC 080 Trichosporon pullulans + TX, Trichosporon spp. + TX, Trichothecium spp. + TX, Trichothecium roseum + TX, Typhula phacorrhiza strain 94670 + TX, Typhula phacorrhiza strain 94671 + TX, Ulocladium atrum + TX, Ulocladium oudemansii Ustilago maydis + TX, various bacteria, and supplemental nutrients Various fungi Verticillium chlamydosporium + TX, Verticillium lecanii Vip3Aa20 Virgibaclillus marismortui+TX, Xanthomonas campestris pv.Poae Xenorhabdus burnetii+TX, and Xenorhabdus nematophila+TX;

[0786] Plant extracts, including pine oil Azadirachtin Plant IGR canola oil Chenopodium ambrosioides near ambrosioides Chrysanthemum Extract Neem oil extract Labiatae essential oil Clove-Rosemary-Peppermint and Thyme Oil Extracts Betaine Garlic + TX, lemongrass oil Neem oil + TX, catnip (Nepeta cataria) (catnip oil) + TX, Nepeta catarina + TX, nicotine + TX, oregano oil Pedaliaceae oil Pyrethrum + TX, Soapbark Tree (Quillaja saponaria) Rotenone Rutaceae plant extracts soybean oil Melaleuca alternifolia extract (also known as tea tree oil) Thyme oil + TX, Rosemary-sesame-peppermint-thyme and cinnamon extract blend Clove-rosemary and peppermint extract blend Clove-Peppermint-Garlic Oil and Mint Blend Kaolin Storage glucans from brown algae

[0787] Pheromones, including: Black-headed firefly pheromone Codling moth pheromone Grape leaf roller pheromone Leaf roller pheromone Housefly pheromone (Muscamone) Pear borer pheromone Peachtree Borer pheromone Tomato Pinworm Pheromone Entostat powder (from palm tree extract) (3E,8Z,11Z)-3,8,11-tetradecatriene acetate + TX, (7Z,11Z,13E)-7,11,13-hexadecatrienal + TX, (E,Z)-7,9-dodecadien-1-yl acetate + TX, 2-methyl-1-butanol + TX, calcium acetate + TX, Lavandulylsenecioate+TX;

[0788] Macrobial agents include: Short-spur Aphid Wasp + TX, Al Aphid Wasp Acerophagus papaya+TX, two-spotted ladybug Two-spotted ladybug Two-spotted ladybug Cocoon jumping wasp + TX, nest moth polyembryonic jumping wasp + TX, Anderson's blunt mite Amblyseius californicus Amblyseius cucumber mite Pseudoamniseius Amblyseius skrjabini Amblyseius osbornei Whitefly wasp + TX, original cherry winged wasp + TX, dark-bellied long-line jumping wasp + TX, Kama long-line jumping wasp + TX, Anagyrusloecki + TX, mealybug long-line jumping wasp Red wax scale flat-horned jumping wasp + TX, golden wasp + TX, woodland flower bug Short-spurred aphid wasp Short-spurred aphid wasp + TX, cotton aphid parasitic wasp Alcyonidae Tobacco aphid wasp + TX, peach red aphid wasp Aphid midge Aphid midge Lingnan yellow aphid wasp + TX, Indian yellow aphid wasp + TX, Ha's long-tailed biting wasp + TX, ant-shaped winged beetle Bombus species + TX, European bumblebee European Bumblebee Coffee berry borer parasitic wasp + TX, black-backed ladybug + TX, common lacewing Common lacewings Red lacewings + TX, exquisite flat-horned wasp + TX, four-banded sergi wasp + TX, white star orange biting wasp + TX, eucalyptus flat-horned golden wasp + TX, flat-horned golden wasp species + TX, tiny broad shield biting wasp Aphid wasp + TX, Aphid wasp + TX, Coccinella spp. + TX, Coccinella plutellae + TX, Cryptochilus moniliformis Japanese square-headed beetle + TX, Siberian gnathid + TX, Siberian gnathid Pea leafminer Diptera small black ladybug Delphastus pusillus+TX, Diachasmimorpha krausii+TX, Diaparsis jucunda+TX, Ali louse-eating wasp+TX, Pea leafminer wasp+TX, Pea leafminer wasp Siberian Braconidia Species of the genus Diplocera+TX, Aphididae+TX, Aphididae Psammocerus spp Goden aphid wasp + TX, Haidian aphid wasp + TX, thin flat hoverfly Eretmocerissiphonini+TX, Californian scimitar wasp+TX, scimitar wasp Psammocerus spp Heinrichthys+TX, Heinrichthys Eretmocerus siphonini+TX, Four-spotted Light-edged Ladybird+TX, Mite-eating Gall Midge Acarid gall midge Alishan Flyminer + TX, Fopius ceratitivorus + TX, Formononetin Slender-waisted Thrips Western static mite + TX, Scleroderma hornbeak + TX, Lycosa axyridis + TX, Harmonia axyridis Heterorhabditis species Heterorhabditis bacteriovorus Heterorhabditis elegans Spotted long-legged ladybug + TX, pointed narrow shield mite Shield mite Black branch gall wasp + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Tricolor spur wasp + TX, citrus powdery scale parasitic wasp Long-horned jumping wasp + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Green fly Tea-footed aphid wasp + TX, blind bug Mesoseiulus longipes+TX, Yellow broad-stalked jumping wasp+TX, Metaphycus lounsburyi+TX, Corner vein brown lacewing Yellow-winged jumping wasp + TX, Muscidifurax raptorellus and Spalangia cameroni Neodryinus typhlocybae+TX, Neodryinus californicus+TX, Neodryinus typhlocybae cucumber Nesideocoris tenuis + TX Bronze Blackfly Cunning flower stink bug Hairless flower stink bug Big-hipped flower bug Small black stink bug Pauesia juniperorum+TX、Phasmarhabditis hermaphrodita+TX、 Phymastichus coffea+TX, Phytoseiidae coarse hair mite+TX, Phytoseiidae chilensis Spotted-bellied stink bug Pseudacteon curvatus + TX, Pseudacteon obtusus + TX, Pseudacteon tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicana + TX, Psyttalia concolor (complex) + TX, Psyttalia species + TX, Rhyzobius lophanthae + TX, Australian ladybird + TX, Rumina decollate + TX, Semielacher petiolatus + TX, and wheat aphid Steinernema carinata Steinernema carinata Sawfly nematode Stenotrophomonas rapis Mole cricket Steinernema carinata Steinernematid species + TX, Steinernematid species Deep-spotted mite-feeding ladybug Bright-bellied Glaze Wasp+TX, Chinese Long-tailed Wasp+TX, Thropobius semiluteus+TX, Chinese Long-tailed Wasp+TX, Cabbage Moth Trichogrammatus Trichogramma brassicae Trichogramma spp.+TX, Trichogramma spp.+TX, Trichogramma spp.+TX, Trichogramma spp.+TX, Trichogramma spp.+TX, Trichogramma spp.+TX, Trichogramma spp.+TX;

[0789] Other biological agents, these other biological agents include: abscisic acid + TX, Chondrostereum purpureum Colletotrichum spp. Copper octanoate Delta trap Erwinia amylovora (Harpin) Fatty acids derived from natural by-products of extra virgin olive oil Ferric phosphate Funneltrap Grower's Homo-brassonolide + TX, iron phosphate MCP hail trap Parasitic insects Microctonushyperodae + TX, Mycoleptodiscus terrestris Pheromone Net potassium bicarbonate Potassium salts of fatty acids Potassium silicate solution +TX, potassium iodide + potassium thiocyanate Spider venom + TX, locust microsporidia Sticky catch and the catch

[0790] (1) An antibacterial agent selected from the group consisting of:

[0791] (1.1) Bacteria, examples of which are Bacillus mojavensis strain R3B (accession number NCAIM (P) B001389) (WO 2013 / 034938), from Certis USA LLC +TX; Bacillus pumilus, in particular strain BU F-33, with NRRL accession number 50185 (from BASF); EPA registration number 71840-19) + TX; Bacillus subtilis, in particular strain QST713 / AQ713 (SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, USA, with NRRL registration number B21661, U.S. Patent No. 6,060,051) + TX; Bacillus subtilis strain BU1814, (from BASF SE PLUS, FLEX and EXTRA) + TX; Bacillus subtilis variant amyloliquefaciens strain FZB24, with registration number DSM 10271 (available as or ECO (EPA registration number 70127-5) obtained from Novozymes) + TX; Bacillus subtilis CX-9060 + TX from Certis USA LLC; Bacillus species, specifically strain D747 (available as DOUBLE obtained from Kumiai Chemical Industry Co., Ltd.) with accession number FERM BP-8234, U.S. Patent No. 7,094,592+TX; Paenibacillus sp. strains with accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016 / 154297+TX; Paenibacillus polymyxa, particularly strain AC-1 (e.g., from Green Biotech Company Ltd.) ) + TX; Pantoea agglomerans, in particular strain E325 (accession number NRRL B-21856) (available as BLOOMTIME BIOLOGICAL TM FD BIOPESTICIDE (from Northwest AgriProducts) + TX; Pseudomonas proradix (e.g., from Sourcon Padena) )+TX; and

[0792] (1.2) Fungi, examples of which are Aureobasidium pullulans, in particular blastospores of strain DSM 14940, blastospores of strain DSM 14941 or a mixture of blastospores of strains DSM 14940 and DSM 14941 (e.g., blastospores from bio-ferm, Switzerland). and BLOSSOM )+TX; Pseudozyma aphidis (as disclosed in WO 2011 / 151819 by Yissum Research Development Company of the Hebrew University of Jerusalem)+TX; Saccharomyces cerevisiae, in particular strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 (as disclosed in WO 2010 / 086790, from Lesaffre et Compagnie, France)+TX;

[0793] (2) Biofungicides selected from the group consisting of:

[0794] (2.1) Bacteria, an example of which is Agrobacterium radiobacterium strain K84 (e.g., from AgBioChem, California) )+TX; radiobacterium strain K1026 (e.g. NOGALL from BASF TM )+TX; Bacillus subtilis variant amyloliquefaciens strain FZB24, with registration number DSM 10271 (available as or ECO (EPA registration number 70127-5) obtained from Novozymes) + TX; Bacillus amyloliquefaciens, specifically strain D747 (available as Double Nickel TM obtained from Kumihiko Chemical Industries, Ltd., with accession number FERM BP-8234, U.S. Patent No. 7,094,592) + TX; Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL accession number B-50768, WO 2014 / 028521) (from Marrone Bio Innovations )+TX; Bacillus amyloliquefaciens strain FZB42, registration number DSM 23117, (can be used as from ABiTEP, Germany) + TX; Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN from the University of Pretoria); TM)+TX; Bacillus licheniformis, in particular strain SB3086, having accession number ATCC 55406, WO 2003 / 000051 (available as Biofungicides and Green Release TM Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (from FMC Corporation) (WG) and (WP)) + TX; Bacillus methylotrophicus strain BAC-9912 (from the Institute of Applied Ecology, Chinese Academy of Sciences) + TX; Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) (WO 2013 / 034938), from Certis USA LLC + TX; Bacillus mycoides isolate with accession number B-30890 (available as BMJ or WG and LifeGard TM obtained from Surtice USA) + TX; Bacillus pumilus, specifically strain QST2808 (available as obtained from Bayer CropScience, USA, with registration number NRRL B-30087 and described in US Pat. No. 6,245,551) + TX; Bacillus pumilus, in particular strain GB34 (available as Yield pumilus, in particular strain BUF-33, having NRRL accession number 50185 (available as part of the CARTISSA product from BASF, EPA accession number 71840-19) + TX; Bacillus subtilis, in particular strain QST713 / AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience in the United States, having NRRL accession number B21661, and described in U.S. Patent No. 6,060,051) + TX; Bacillus subtilis Y1336 (available as WP was obtained from Bion-Tech, Taiwan, China, and registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096, and 5277) + TX; Bacillus subtilis strain MBI 600 (available as SUBTILEX from BASF, with registration number NRRL B-50595, U.S. Patent No. 5,061,495) + TX; Bacillus subtilis strain GB03 (available as obtained from Bayer AG, Germany) + TX; Bacillus subtilis strain BU1814, (available as PLUS, FLEX and EXTRA obtained from BASF) + TX; Bacillus subtilis CX-9060 + TX from Certis USA LLC; Bacillus subtilis KTSB strain (from Donaghys )+TX; Bacillus subtilis IAB / BS03 (AVIV from STK Bio-Ag Technologies) TM , from Idai Nature )+TX; Bacillus subtilis strain Y1336 (can be used as WP was obtained from Biotech, Taiwan, China, and registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096, and 5277) + TX; Paenibacillus epiphyticus (WO 2016 / 020371) from BASF + TX; Paenibacillus polymyxa plantarum species (WO 2016 / 020371) from BASF + TX; Paenibacillus species strains with registration number NRRL B-50972 or registration number NRRL B-67129, WO 2016 / 154297 + TX; Pseudomonas chlororaphis strain AFS009 with registration number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER from AgBiomeInnovations, USA) TM and ) + TX; Pseudomonas chlororaphis strains, in particular strain MA342 (e.g., from Bioagri and Koppert); and )+TX; Pseudomonas fluorescens strain A506 (e.g., from NuFarm A506) + TX; Pseudomonas proradix (e.g., from Soconpadna ) + TX; Streptomyces griseoviridis strain K61 (also known as Streptomyces luteus strain K61) (accession number DSM 7206) (from Verdera BioWorks See Crop Protection 2006, 25, 468-475) + TX; Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (from Novozymes and )+TX; and

[0795] (2.2) Fungi, an example of which is Pseudomonas aeruginosa, in particular strain AQ 10 (e.g. AQ from Intrachem Bio Italia) ) + TX; Pseudomonas aeruginosa strain AQ10, with accession number CNCM1-807 (e.g., AQ from Intrachem Biologia Italia S.A. )+TX; Aspergillus flavus strain NRRL 21882 (as a and known products) + TX; budding mold, especially the spores of strain DSM14940 + TX; budding mold, especially the spores of strain DSM 14941 + TX; budding mold, especially the mixture of spores of strains DSM14940 and DSM 14941 (for example, from Bio-Philippe Co., Ltd., Switzerland )+TX; Chaetomium cupreum (accession number CABI 353812) (e.g., BIOKUPRUM from AgriLife TM )+TX; Chaetomium globosum (can be used as from Rivale) + TX; Cladosporium cladosporioides, strain H39, with accession number CBS122244, US2010 / 0291039 (from Wageningen Research Foundation (Stichting Dienst Landbouwkundig Onderzoek)) + TX; Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM9660, e.g., from Bayer CropScience Biologics GmbH) + TX; )+TX; Cryptococcus flavescens, strain 3C (NRRL Y-50378), (B2.2.99)+TX; Dactylaria candida+TX; Dilophosphora alopecuri (can be used as TWIST Obtain) + TX; Fusarium oxysporum, strain Fo47 (can be used as obtained from Natural Plant Protection) + TX; Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g., from Lallemand) )+TX; Gliocladium roseum (also known as Clonostachys rosea), in particular strain 321U from Adjuvants Plus, strain ACM941 as disclosed in Xue AG (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can. J. Plant Sci. 2003, 83(3):519-524), or strain IK726 (Jensen DF et al. Development of a biocontrol agent for plant disease control with special emphasis on the nearcommercial fungal antagonist Clonostachys rosea). strain 'IK726' [with particular emphasis on the development of a biocontrol agent for plant disease control using the near-commercial fungal antagonist Gliocladium roseum strain 'IK726'], Australasian Plant Pathol. 2007, 36(2), 95-101) + TX; conidia of Lecanicillium lecanii (formerly Verticillium lecanii) strain KV01 (e.g., from Corbett / Arysta )+TX; Metschnikowia fructicola, in particular strain NRRL Y-30752, (B2.2.3)+TX; Microsphaeropsis ochracea+TX; Muscodor roseus, in particular strain A3-5 (accession number NRRL 30548)+TX; Penicillium steckii (DSM 27859, WO 2015 / 067800) from BASF+TX; Penicillium vermiculatum+TX; Phlebiopsis gigantea strain VRA 1992 (from Danstar Ferment) C) + TX; Pichia anomala, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183 + TX; Pseudozyma flocculosa, strain PF-A22 UL (can be used as L obtained from Plant Products Co., California) + TX; Saccharomyces cerevisiae, specifically strain LASO2 (from Agro-Levures et Dérivés), strain LAS117 cell wall (from Lesaffre From BASF ), strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM No. 1-3939 (WO 2010 / 086790) + TX from Lesaffre, France; Simplicillium lanosoniveum + TX; Talaromyces flavus, strain V117b + TX; Trichoderma asperelloides JM41R (registration number NRRL B-50759) (from TRICHO )+TX; Trichoderma asperellum, in particular strain kd (e.g., T-Gro from Andermatt Biocontrol)+TX; Trichoderma asperellum, in particular strain SKT-1, with accession number FERM P-16510 (e.g., ), strain T34 (e.g., T34 from Biocontrol Technologies SL, Spain) or strain ICC 012+TX from Isagro; Trichoderma atroviride, in particular strain SC1 (accession number CBS122089, WO 2009 / 116106 and U.S. Pat. No. 8,431,120 (from Bi-PA), strain 77B (T77 from Andermat Biocontrol) or strain LU132 (e.g., Sentinel from Agrimm Technologies Limited)+TX; Trichoderma atroviride, strain CNCM 1-1237 (e.g., Sentinel from Agrauxine, France) WP) + TX; Trichoderma viride, strain No. V08 / 002387 + TX; Trichoderma viride, strain NMI No. V08 / 002388 + TX; Trichoderma viride, strain NMI No. V08 / 002389 + TX; Trichoderma viride, strain NMI No. V08 / 002390 + TX; Trichoderma viride, strain LC52 (e.g., Tenet from Agri-Mount Technology Co., Ltd.) + TX; Trichoderma viride, strain ATCC 20476 (IMI 206040) + TX; Trichoderma viride, strain T11 (IMI352941 / CECT20498) + TX; Trichoderma viride, strain SKT-1 (FERM P-16510), Japanese Patent Publication (Kokai) 11-253151A + TX; Trichoderma viride, strain SKT-2 (FERM P-16511), Japanese Patent Publication (Kokai) 11-253151A+TX; Dark green Trichoderma, strain SKT-3 (FERM P-17021), Japanese Patent Publication (Kokai) 11-253151A+TX; Trichoderma fertile (for example, the product TrichoPlus from BASF) + TX; Trichoderma gamsii (original green Trichoderma), strain ICC080 (IMI CC392151CABI, for example, BioDerma from AGROBIOSOL DE MEXICO, SADE CV) + TX; Trichoderma gamsii (original green Trichoderma), strain ICC 080 (IMI CC392151CABI) (can be used as obtained from Agribelso Mexico) + TX; Trichoderma harmatum + TX; Trichoderma harmatum, with accession number ATCC 28012 + TX; Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Kobert) or strain Cepa SimbT5 (from Simbiose Agro) + TX; Trichoderma harzianum + TX; Trichoderma harzianum slant (rifai) T39 (e.g., from Makhteshim, USA) )+TX; Trichoderma harzianum, strain ITEM 908 (e.g., Trianum-P from Kobert)+TX; Trichoderma harzianum, strain TH35 (e.g., Root-Pro from Mycontrol)+TX; Trichoderma harzianum, strain DB 103 (can be used as 7456 from Dagutat Biolab) + TX; Trichoderma polysporum, strain IMI 206039 (e.g., Binab TF WP from BINAB Bio-Innovation AB, Sweden) + TX; Trichoderma stromaticum, with accession number Ts3550 (e.g., Tricovab from CEPLAC, Brazil) + TX; Trichoderma ...

Claims

1. A compound of formula (I), in R8 and R9 are independently of one another halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 cycloalkyl, or aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, and C1-C4 alkylsulfonyl; or R8 and R9 together form a group -O-CF2-O-; Q is a group selected from the group consisting of formulae Qa, Qb and Qc The arrows indicate the points of attachment to the double ring; A, A1 and A2 are independently CH or N; X is S, SO, or SO2; R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; R2, R3, R4 and R5 are independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted by cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, -N(R 10 R 11 ), or -N(R 10 )C(=O)R 11 ; R 10 and R 11 are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl; R6 and R7 are independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted by cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy or -N(R 12 )C(=O)R 13 ;and R 12 and R 13 are independently hydrogen, C1-C4 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I.

2. The compound of formula I according to claim 1, which is represented by the following: Among them, X, R1, R2, R3, R8, R9, R 10 and R 11 is an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound as defined under formula I in claim 1 or having formula I-1.

3. The compound of formula I according to claim 1, which is represented by the following: Among them, X, R1, R4, R5, R8, R9, R 10 and R 11 is an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound as defined under formula I in claim 1, or having formula I-2.

4. The compound of formula I according to claim 1, which is represented by the following: Among them, A, A1, A2, X, R1, R6, R7, R8, R9, R 12 and R 13 is an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound as defined under formula I in claim 1 or having formula I-3.

5. A compound of formula I according to any one of claims 1 to 4, wherein X is S or SO2; and R1 is ethyl or cyclopropylmethyl.

6. The compound of formula I according to claim 1, which is represented by the following: Compound of formula I-4 in Q1 is a group selected from the group consisting of formulae Q1a, Q1b, and Q1c, wherein the arrow indicates the point of attachment to the nitrogen atom of the tricyclic ring; And among them A, A1, A2, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 、R 12 and R 13 is an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound as defined under formula I in claim 1 or having formula I-4.

7. A compound of formula I according to any one of claims 1, 2 and 6, wherein R2 and R3 are independently hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropyloxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

8. The compound of formula I according to claim 7, wherein R2 is hydrogen and R3 is hydrogen, chloro, bromo, iodo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl); Or R3 is hydrogen and R2 is chloro, bromo, iodo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

9. A compound of formula I according to any one of claims 1, 3 and 6, wherein R4 and R5 are independently hydrogen, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropyloxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

10. The compound of formula I according to claim 9, wherein R4 is hydrogen and R5 is hydrogen, chloro, bromo, iodo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl); Or R5 is hydrogen and R4 is chloro, bromo, iodo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

11. A compound of formula I according to any one of claims 1, 4 and 6, wherein R6 and R7 are independently hydrogen, chlorine, bromine, difluoromethyl, trifluoromethyl, difluoroethyl, trifluoromethoxy, trifluoroethoxy, difluoromethoxy, cyanoisopropyloxy, difluoropropoxy, difluoroethoxy, cyclopropyl, cyanoisopropyl, cyanocyclopropyl, -NHC(O)CH3, -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

12. The compound of formula I according to claim 11, wherein R6 is hydrogen and R7 is hydrogen, chloro, bromo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl); Or R7 is hydrogen and R6 is chloro, bromo, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, trifluoromethoxy, -OCH2CF3, difluoromethoxy, 1-cyano-1-methyl-ethoxy, 2,2-difluoropropoxy, 2,2-difluoroethoxy, cyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyanocyclopropyl, -NHC(O)CH3, -NCH3C(O)CH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl).

13. A compound of formula I according to any one of the preceding claims, wherein R8 and R9 are each independently halogen, trifluoromethyl, 1,1-difluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl, or aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, trifluoromethyl, -OCHF2, -OCF3, trifluoromethylsulfanyl, trifluoromethylsulfinyl, and trifluoromethylsulfonyl; Alternatively, R8 and R9 together form a group -O-CF2-O-.

14. The compound of formula I according to claim 13, wherein R8 is hydrogen and R9 is fluorine, chlorine, bromine, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or R9 is hydrogen and R8 is fluorine, chlorine, bromine, trifluoromethyl, 1,1-difluoroethyl, -OCHF2, -OCF3, -OCH2CHF2, -OCH2CF3, cyclopropyl or 4-F-phenyl; or R8 and R9 together form a group -O-CF2-O-.

15. A compound of formula I according to any one of claims 1, 4, 6 and 11-14, wherein A is N, and A1 and A2 are CH.

16. The compound of claim 1 having formula I, which is selected from: 3-[3-Ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(trifluoro-methyl)chromen-4-one.

17. A composition comprising an insecticidal, acaricidal, nematicidal or molluscicidal effective amount of a compound of formula (I) according to any one of claims 1 to 16, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, and optionally an adjuvant or diluent.

18. A method for combating and controlling insects, acarids, nematodes or molluscs, which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) according to any one of claims 1 to 16, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, or a composition according to claim 17 to the pest, the site of the pest, or a plant susceptible to attack by the pest.

19. A method for protecting plant propagation material from attack by insects, mites, nematodes or molluscs, said method comprising treating said propagation material or the locus where said propagation material is planted with a composition according to claim 17.

Images