Heterocyclic derivatives having pesticidally active sulfur-containing substituents - Patent Application 20070229633

Abstract

The substituents are as defined in claim 1. JPEG2024539980000072.jpg37158. 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 the compounds or compositions for combating, preventing or controlling animal pests, including in particular arthropods such as insects, mollusks, nematodes or representatives of the order Acarina, in agriculture or horticulture.

Description

[Technical Field]

[0001] The present invention relates to pesticidally active, in particular insecticidally active, heterocyclic derivatives containing sulfur substituents, processes for their preparation, compositions containing these compounds, and their use for controlling animal pests, including arthropods and in particular insects or representatives of the order Acarina. [Background technology]

[0002] Heterocyclic derivatives containing sulfur substituents are known and are described, for example, in WO 2019 / 131575, WO 2019 / 131587, WO 2020 / 158889, WO 2020 / 171077, WO 2020 / 203763, WO 2021 / 141106, WO 2020 / 178789 and WO 2021 / 033141. Summary of the Invention [Means for solving the problem]

[0003] Surprisingly, it has now been found that certain novel sulfur-containing phenyl and pyridyl derivatives attached to an (aza)chromenone moiety have favorable properties as pesticides.

[0004] The present invention therefore provides a compound of formula I [ka] (In the formula, R2 is C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or C1-C6 haloalkoxy; G is CH or N; X1 is O, S or NR6, where R6 is C1-C4 alkyl; R7 is hydrogen, C1-C4 alkyl or halogen; Q is a function of the formula Qa and Qb [ka] (wherein the arrow indicates the point of attachment to the bicyclic ring; and A represents CH or N; X is S, SO, SO2; R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; Q1 is hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, C1-C6 haloalkoxy, -N(R4)2, -N(R4)COR5 or 2-pyridyloxy; or Q1 is a 5- to 6-membered aromatic or heteroaromatic ring system bonded via a ring carbon atom to a ring containing substituent A, said ring system being unsubstituted or mono- or polysubstituted with substituents 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; and said ring system may contain one, two or three ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein said ring system may not contain more than one ring oxygen atom and may not contain more than one ring sulfur atom; or Q1 is a 5-membered aromatic heterocyclic ring system bonded to a ring containing substituent A via a ring nitrogen atom, said ring system being unsubstituted or mono- or polysubstituted with substituents 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; and said ring system contains 1, 2 or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein said ring system contains at least one ring nitrogen atom and may not contain more than one ring oxygen atom and may not contain more than one ring sulfur atom; R3 is hydrogen or C1-C4 alkyl; each R4 is independently hydrogen, C1-C4 alkyl, or C3-C6 cycloalkyl; and R5 is C1-C6 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl. is a group selected from the group consisting of to provide.

[0005] The present invention also provides agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of compounds of formula I. DETAILED DESCRIPTION OF THE INVENTION

[0006] Compounds of formula I having at least one basic centre can, for example, form acid addition salts 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, for example C1-C4 alkanecarboxylic acids which are unsubstituted or substituted, for example, by halogens, such as acetic acid; saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid; hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or for example benzoic acid; or organic sulfonic acids, for example C1-C4 alkane- or arylsulfonic acids which are unsubstituted or substituted, for example, by halogens, such as methane- or p-toluenesulfonic acid. Compounds of formula I having at least one acidic group can, for example, form salts with bases, for example inorganic salts, for example alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or organic amines, for example morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or mono-, di- or trihydroxy-lower alkylamines, for example mono-, di- or triethanolamine.

[0007] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as N-oxides, or in salt form, for example in agriculturally usable salt form.

[0008] N-oxides are oxidized forms of tertiary amines or nitrogen-containing aromatic heterocyclic compounds, as described, for example, in the book "Heterocyclic N-oxides", A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0009] The compounds of formula I according to the present invention also include the hydrates which may be formed during salt formation.

[0010] When substituents themselves are described as being further substituted, this means that they bear one or more equal or different substituents, for example, 1 to 4 substituents. Typically, no more than three such optional substituents are present at one time. Preferably, no more than two such substituents are present at one time (i.e., the group is substituted with one or two of the listed substituents). When the additional substituent is a larger group such as cycloalkyl or phenyl, it is most preferred that only one of such optional substituents is present. When a group, e.g., alkyl, is described as being substituted, this includes groups that are part of another group, e.g., alkyl in alkylthio.

[0011] As used herein, "C1-C nThe term "alkyl" refers to a saturated straight or branched hydrocarbon group having 1 to n carbon atoms attached via any of the carbon atoms, such as any one 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.

[0012] As used herein, "C1-C nThe term "haloalkyl" refers to a straight or branched saturated alkyl group (as defined above) having 1 to n carbon atoms attached via any of the carbon atoms, 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, 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, and any one of 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, and nonafluorobutyl. Thus, the term "C1-C2 fluoroalkyl" refers to a C1-C2 alkyl group having 1, 2, 3, 4 or 5 fluorine atoms, such as any one of difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl.

[0013] As used herein, "C1-C nThe term "alkoxy" refers to a straight or branched saturated alkyl group (as defined above) having 1 to n carbon atoms attached through an oxygen atom, i.e., any one of, for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy.

[0014] As used herein, "C1-C n The term "haloalkoxy" refers to any of the above C1-C alkyl groups partially or fully substituted with fluorine, chlorine, bromine and / or iodine. n alkoxy groups, i.e., for example, 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, 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.

[0015] As used herein, "C1-C nThe term "-alkylsulfanyl" refers to a straight or branched saturated alkyl group having 1 to n carbon atoms (as defined above) attached through a sulfur atom, i.e., any one of methylthio, ethylthio, n-propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, or 1,1-dimethylethylthio.

[0016] As used herein, "C1-C n The term "alkylsulfinyl" refers to a straight or branched saturated alkyl group having 1 to n carbon atoms (as defined above) attached through the sulfur atom of a sulfinyl group, i.e., any one of, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethyl-ethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl or 1-ethylpropylsulfinyl.

[0017] As used herein, "C1-C n The term "alkylsulfonyl" refers to a straight or branched saturated alkyl group having 1 to n carbon atoms (as defined above) attached through the sulfur atom of a sulfonyl group, i.e., any one of methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, or t-butylsulfonyl.

[0018] As used herein, "C1-C n The term "haloalkylsulfanyl" refers to any of the above C1-C alkyls which are partially or fully substituted with fluorine, chlorine, bromine and / or iodine. nIt refers to an alkylthio group, i.e., for example, 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, 3-fluoropropylthio, 2-chloro- Heptafluoropropylthio refers to any one of 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(chloromethyl)-2-bromoethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, and 4-bromobutylthio.

[0019] "C1~C n Haloalkylsulfinyl" and "C1-C n The term "haloalkylsulfonyl" refers to the above groups but with sulfur in the 1 or 2 oxidation state, respectively.

[0020] As used herein, "C1-C n The term "cyanoalkyl" refers to a linear or branched saturated alkyl group having 1 to n carbon atoms (as defined above) substituted with a cyano group, such as cyanomethylene, cyanoethylene, 1,1-dimethylcyanomethyl, cyanomethyl, cyanoethyl, and 1-dimethylcyanomethyl.

[0021] "C1~C nThe term "cyanoalkoxy" refers to the above groups but attached through an oxygen atom.

[0022] As used in this specification, "C3 to C n The suffix "-C1-C cycloalkyl" after a term such as "-C1-C cycloalkyl" (where n is an integer from 1 to 6) n Alkyl is C3 to C n It refers to a linear or branched saturated alkyl group substituted with a cycloalkyl. C3-C n Cycloalkyl-C1~C n An example of alkyl is for example cyclopropylmethyl.

[0023] As used herein, the term "C3-C6 cycloalkyl" refers to 3- to 6-membered cycloylkyl groups such as cyclopropane, cyclobutane, cyclopropane, cyclopentane, and cyclohexane.

[0024] As used herein, a "C3-C monosubstituted with cyano" is n The term "cycloalkyl" refers to a saturated or partially saturated monocyclic-, bicyclic-, or tricyclic hydrocarbon having 3 to n carbon atoms (as defined above) substituted with a cyano group.

[0025] Halogen is generally fluorine, chlorine, bromine or iodine. This applies correspondingly to halogen in combination with other meanings, such as haloalkyl.

[0026] In the context of the present invention, "mono- or polysubstituted" in the definition of the Q1 substituent typically means mono- to penta-substituted, more preferably mono-, di- or tri-substituted, depending on the chemical structure of the substituent.

[0027] In the context of the present invention, the phrases "Q1 is a 5- to 6-membered aromatic or heteroaromatic ring system bonded via a ring carbon atom..." and "Q1 is a 5-membered aromatic heterocyclic ring system bonded via a ring nitrogen atom..." refer to specific embodiments of the mode of attachment of the substituent Q1 to the group Q of formula Qa or Qb (which can optionally be pyridyl or phenyl when A represents N or CH, respectively), where Q is also substituted by X-R1 and R3 as described above.

[0028] In the context of the present invention, examples of "Q1 is a 5-6 membered aromatic or heteroaromatic ring system bonded via a ring carbon atom...; and said ring system may contain 1, 2 or 3 heteroatoms..." include, but are not limited to, phenyl, pyrazolyl, triazolyl, pyridinyl and pyrimidinyl; preferably phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidin-2-yl, pyrimidin-4-yl and pyrimidin-5-yl.

[0029] In the context of the present invention, examples of "Q1 is a 5-membered aromatic heterocyclic ring system bonded via a ring nitrogen atom...; and said ring system contains 1, 2 or 3 heteroatoms..." are particularly, but not limited to, pyrazolyl, pyrrolyl, imidazolyl and triazolyl; preferably pyrrol-1-yl, pyrazol-1-yl, triazol-2-yl, 1,2,4-triazol-1-yl, triazol-1-yl and imidazol-1-yl.

[0030] Certain embodiments of the present invention are provided as described below.

[0031] Embodiment 1 provides a compound of formula I, as defined above, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof.

[0032] Embodiment 2 provides a compound according to embodiment 1, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, wherein Q is Qa and has the preferred values ​​for R2, G, X1, R6, R7, A, X, R1, Q1, R3, R4, and R5 described below.

[0033] Embodiment 3 provides a compound of embodiment 1, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, wherein Q is Qb and has the preferred values ​​for R2, G, X1, R6, R7, A, X, R1, Q1, R3, R4, and R5 described below.

[0034] For embodiments 1-3, preferred values ​​for R2, G, X1, R6, R7, A, X, R1, Q1, R3, R4, and R5, in any combination thereof, are as set forth below. Preferably, R2 is C1-C2 fluoroalkyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl or C1-C2 fluoroalkoxy.

[0035] It is also preferred that R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy.

[0036] More preferably, R2 is -CF3, -CF2CF3, -CHF2, -SCF3, -SO2CF3, -OCF3 or -OCHF2.

[0037] Even more preferably, R2 is -CF3, -SO2CF3, -OCF3 or -OCHF2.

[0038] Most preferably, R2 is -CF3, -OCF3 or -OCHF2.

[0039] Preferably, G is CH or N.

[0040] Most preferably, G is CH.

[0041] Preferably, X1 is O, S or N(C1-C2 alkyl).

[0042] More preferably, X1 is O, S or NCH3.

[0043] Most preferably, X1 is O.

[0044] Preferably, R6 is a C1-C2 alkyl.

[0045] More preferably, R6 is methyl or ethyl.

[0046] Most preferably, R6 is methyl.

[0047] Preferably, R7 is hydrogen, C1-C2 alkyl or chloro.

[0048] More preferably, R7 is hydrogen or methyl.

[0049] Most preferably, R7 is hydrogen.

[0050] Preferably, A is N or CH.

[0051] Most preferably, A is N.

[0052] Preferably, X is S or SO2.

[0053] Most preferably, X is SO2.

[0054] Preferably, R1 is C1-C4 alkyl or cyclopropyl-C1-C4 alkyl.

[0055] More preferably, R1 is ethyl or cyclopropylmethyl.

[0056] Most preferably, R1 is ethyl.

[0057] When Q is Qa, preferably Q1 is hydrogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, C1-C6 haloalkoxy, -N(R4)COR5 or 2-pyridyloxy.

[0058] Also preferably, when Q1 is a 5- to 6-membered aromatic or heteroaromatic ring system bonded to a ring containing substituent A via a ring carbon atom, the ring system is unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, cyano, and C1-C4 haloalkyl; and the ring system may contain one or two ring nitrogen atoms.

[0059] Also preferably, when Q1 is a 5-membered aromatic heterocyclic ring system bonded to a ring containing substituent A via a ring nitrogen atom, said ring system is unsubstituted or mono-substituted with a substituent selected from the group consisting of halogen, cyano and C1-C4 haloalkyl; and said ring system contains 2 or 3 ring nitrogen atoms.

[0060] More preferably, Q1 is hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, -N(R4)COR5 (wherein R4 is hydrogen or methyl and R5 is methyl, ethyl or cyclopropyl); or Q1 is N-linked pyrazolyl which may be monosubstituted with 2-pyridyloxy, chloro, cyano or trifluoromethyl; or Q1 is N-linked triazolyl or C-linked pyrimidinyl.

[0061] Most preferably, Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 2-pyridyloxy, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0062] When Q is Qb, preferably Q1 is hydrogen, C3-C6 cycloalkyl, -N(R4)2 or -N(R4)COR5.

[0063] Also preferably, when Q1 is a 5- to 6-membered aromatic or heteroaromatic ring system bonded to a ring containing substituent A via a ring carbon atom, the ring system is unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, cyano, and C1-C4 haloalkyl; and the ring system may contain one or two ring nitrogen atoms.

[0064] Also preferably, when Q1 is a 5-membered aromatic heterocyclic ring system bonded to a ring containing substituent A via a ring nitrogen atom, said ring system is unsubstituted or mono-substituted with a substituent selected from the group consisting of halogen, cyano and C1-C4 haloalkyl; and said ring system contains 2 or 3 ring nitrogen atoms.

[0065] More preferably, Q1 is hydrogen, cyclopropyl, -N(R4)2 or -N(R4)COR5 (wherein in each of these, R4 is independently hydrogen or methyl, and R5 is methyl, ethyl or cyclopropyl); or Q1 is N-linked triazolyl or C-linked pyrimidinyl.

[0066] Most preferably, Q1 is hydrogen, cyclopropyl, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0067] Preferably, R3 is hydrogen or C1-C4 alkyl.

[0068] More preferably, R3 is hydrogen or methyl.

[0069] Most preferably, R3 is hydrogen.

[0070] Preferably, each R4 is independently hydrogen or C1-C4 alkyl.

[0071] Most preferably, each R4 is independently hydrogen or methyl.

[0072] Preferably, R5 is C1-C6 alkyl or C3-C6 cycloalkyl.

[0073] More preferably, R5 is methyl, ethyl or cyclopropyl.

[0074] Most preferably, R5 is methyl.

[0075] Further embodiments of the present invention are provided as described below.

[0076] A preferred group of compounds of formula I is the compound of formula I-1 [ka] (wherein R2, G, X1, R6, R7, A, X, R1, Q1, R3, R4 and R5 are as defined in formula I above), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-1.

[0077] In a preferred group of compounds of formula I-1, R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N or CH; X is S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, C1-C6 haloalkoxy, 2-pyridyloxy, or -N(R4)COR5 (wherein R4 is hydrogen or methyl and R5 is methyl, ethyl, or cyclopropyl); and R3 is hydrogen or methyl.

[0078] In another preferred group of compounds of formula I-1, R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N or CH; X is S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, 2-pyridyloxy, or -N(R4)COR5 (wherein R4 is hydrogen or methyl, and R5 is methyl, ethyl, or cyclopropyl); and R3 is hydrogen or methyl.

[0079] In another preferred group of compounds of formula I-1, R2 is -CF3, -OCF3 or -OCHF2; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N or CH; X is S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl) or 2-pyridyloxy; and R3 is hydrogen or methyl.

[0080] In another preferred group of compounds of formula I-1, R2 is -CF3, -OCF3 or -OCHF2; G is CH; X1 is O; R7 is hydrogen; A is N; X is SO2; R1 is ethyl; Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl) or 2-pyridyloxy; and R3 is hydrogen.

[0081] In another further preferred group of compounds of formula I-1, Q1 is a 5- to 6-membered aromatic or heteroaromatic ring system bonded via a ring carbon atom to the ring containing substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, cyano, and C1-C4 haloalkyl; and said ring system may contain one or two ring nitrogen atoms. In this embodiment, more preferably, Q1 is C-linked pyrimidinyl.

[0082] Also preferred are compounds of formula I-1 in which Q1 is a 5-membered aromatic heterocyclic ring system bonded to a ring containing substituent A via a ring nitrogen atom, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, cyano, and C1-C4 haloalkyl; and said ring system containing two or three ring nitrogen atoms. In this embodiment, more preferably, Q1 is N-linked pyrazolyl, which may be monosubstituted with chloro, cyano, or trifluoromethyl; or Q1 is N-linked triazolyl.

[0083] In another preferred group of compounds of formula I-1, R2 is -CF3, -OCF3 or -OCHF2; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N or CH; X is S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is N-linked triazolyl, C-linked pyrimidinyl, or N-linked pyrazolyl, which may be monosubstituted with chloro, cyano, or trifluoromethyl; and R3 is hydrogen or methyl.

[0084] In another preferred group of compounds of formula I-1, R2 is -CF3, -OCF3 or -OCHF2; G is CH; X1 is O; R7 is hydrogen; A is N; X is SO2; R1 is ethyl; Q1 is pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl; and R3 is hydrogen.

[0085] In the compounds of formula I-1 and all of the preferred embodiments of compounds of formula I-1 above, unless otherwise specified, R2, G, X1, R6, R7, A, X, R1, Q1, R3, R4 and R5 are as defined in formula I above; Preferably, R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy; most preferably, R2 is -CF3, -OCF3, or -OCHF2; Preferably, G is CH or N; most preferably, G is CH; Preferably, X1 is O, S, or NCH3; most preferably, X1 is O; Preferably, R7 is hydrogen or methyl; most preferably, R7 is hydrogen; Preferably, A is N or CH; most preferably, A is N; Preferably, X is S or SO; most preferably, X is SO; Preferably, R1 is ethyl or cyclopropylmethyl; most preferably, R1 is ethyl; Preferably, Q1 is hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, 2-pyridyloxy, N-linked triazolyl, C-linked pyrimidinyl, N-linked pyrazolyl optionally monosubstituted with chloro, cyano, or trifluoromethyl; or Q1 is -N(R4)COR5 (where R4 is hydrogen or methyl and R5 is methyl, ethyl, or cyclopropyl); most preferably, Q1 is hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, 2-pyridyloxy, N-linked triazolyl, C-linked pyrimidinyl, N-linked pyrazolyl optionally monosubstituted with chloro, cyano, or trifluoromethyl; or Q1 is -N(R4)COR5 (where R4 is hydrogen or methyl, and R5 is methyl, ethyl, or cyclopropyl); most preferably, Q1 is hydrogen, trifluoromethyl, difluoroethyl, 2-pyridyloxy, N-linked triazolyl, C-linked pyrimidinyl, N-linked pyrazolyl optionally monosubstituted with chloro, cyano, or trifluoromethyl; or Q1 is -N(R4)COR5 (where R4 is hydrogen or methyl, and R5 is methyl, ethyl, or cyclopropyl); chloromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 2-pyridyloxy, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl; Preferably, R3 is hydrogen or methyl; most preferably, R3 is hydrogen.

[0086] A further preferred group of compounds according to this embodiment are compounds of formula (I-1), namely compounds of formula (I-1-1), wherein: R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N or CH; X is S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is N-linked pyrazolyl, which may be monosubstituted with hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, 2-pyridyloxy, chloro, cyano, or trifluoromethyl; or Q1 is N-linked triazolyl, C-linked pyrimidinyl, or -N(R4)COR5, where R4 is hydrogen or methyl and R5 is methyl, ethyl, or cyclopropyl; and R3 is hydrogen or methyl.

[0087] A further preferred group of compounds according to this embodiment are compounds of formula (I-1-2), which are compounds of formula (I-1-1), wherein: Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 2-pyridyloxy, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0088] A further preferred group of compounds according to this embodiment are compounds of formula (I-1-3), which are compounds of formula (I-1-1), wherein: Q1 is hydrogen, cyclopropyl, cyanocyclopropyl, cyanoisopropyl or cyanoisopropoxy.

[0089] A further preferred group of compounds according to this embodiment are compounds of formula (I-1-4), which are compounds of formula (I-1-1), wherein: Q1 is hydrogen, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl or 1-cyano-1-methyl-ethoxy.

[0090] A further preferred group of compounds according to this embodiment are compounds of formula (I-1), namely compounds of formula (I-1-5), wherein: R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy, preferably R2 is -CF3, -OCF3 or -OCHF2; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N; X is SO2; R1 is ethyl; Q1 is hydrogen, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl or 1-cyano-1-methyl-ethoxy; and R3 is hydrogen.

[0091] A further preferred group of compounds according to this embodiment are compounds of formula (I-1-6), which are compounds of formula (I-1-5), wherein: G is CH; X1 is O; and R7 is hydrogen or methyl, preferably hydrogen.

[0092] A further preferred group of compounds according to this embodiment are compounds of formula (I-1-7), which are compounds of formula (I-1-5), wherein: G is N; X1 is O; and R7 is hydrogen or methyl, preferably hydrogen.

[0093] Another preferred group of compounds of formula I is the compounds of formula I-2 [ka] (wherein R2, G, X1, R6, R7, A, X, R1, Q1, R3, R4 and R5 are as defined in formula I above), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-2.

[0094] In a preferred group of compounds of formula I-2, R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N or CH; X is S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, C3-C6 cycloalkyl, -N(R4)2, or -N(R4)COR5, in each of which R4 is independently hydrogen or methyl, and R5 is methyl, ethyl, or cyclopropyl; and R3 is hydrogen or methyl.

[0095] In another preferred group of compounds of formula I-2, R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N or CH; X is S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, cyclopropyl, -N(R4)2, or -N(R4)COR5, in each of which R4 is independently hydrogen or methyl, and R5 is methyl, ethyl, or cyclopropyl; and R3 is hydrogen or methyl.

[0096] In another preferred group of compounds of formula I-2, R2 is -CF3, -OCF3 or -OCHF2; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N or CH; X is S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, cyclopropyl, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl); and R3 is hydrogen or methyl.

[0097] In another preferred group of compounds of formula I-2, R2 is -CF3, -OCF3 or -OCHF2; G is CH; X1 is O; R7 is hydrogen; A is N; X is SO2; R1 is ethyl; Q1 is hydrogen, cyclopropyl, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl); and R3 is hydrogen.

[0098] In another further preferred group of compounds of formula I-2, Q1 is a 5- to 6-membered aromatic or heteroaromatic ring system bonded via a ring carbon atom to the ring containing substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, cyano, and C1-C4 haloalkyl; and said ring system may contain one or two ring nitrogen atoms. In this embodiment, more preferably, Q1 is C-linked pyrimidinyl.

[0099] Also preferred compounds of formula I-2 include those in which Q1 is a 5-membered aromatic heterocyclic ring system bonded via a ring nitrogen atom to a ring containing substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, cyano, and C1-C4 haloalkyl; and said ring system containing two or three ring nitrogen atoms. In this embodiment, more preferably, Q1 is an N-linked triazolyl.

[0100] In another preferred group of compounds of formula I-2, R2 is -CF3, -OCF3 or -OCHF2; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N or CH; X is S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is N-linked triazolyl or C-linked pyrimidinyl; and R3 is hydrogen or methyl.

[0101] In another preferred group of compounds of formula I-2, R2 is -CF3, -OCF3 or -OCHF2; G is CH; X1 is O; R7 is hydrogen; A is N; X is SO2; R1 is ethyl; Q1 is 1,2,4-triazol-1-yl or pyrimidin-2-yl; and R3 is hydrogen.

[0102] In the compounds of formula I-2 and all of the preferred embodiments of compounds of formula I-2 above, unless otherwise specified, R2, G, X1, R6, R7, A, X, R1, Q1, R3, R4, and R5 are as defined in formula I above; Preferably, R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy; most preferably, R2 is -CF3, -OCF3, or -OCHF2; Preferably, G is CH or N; most preferably, G is CH; Preferably, X1 is O, S, or NCH3; most preferably, X1 is O; Preferably, R7 is hydrogen or methyl; most preferably, R7 is hydrogen; Preferably, A is N or CH; most preferably, A is N; Preferably, X is S or SO; most preferably, X is SO; Preferably, R1 is ethyl or cyclopropylmethyl; most preferably, R1 is ethyl; Preferably, Q1 is hydrogen, cyclopropyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, or -N(R4)COR5 (wherein in each of these, R4 is independently hydrogen or methyl, and R5 is methyl, ethyl, or cyclopropyl); most preferably, Q1 is hydrogen, cyclopropyl, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 1,2,4-triazol-1-yl, or pyrimidin-2-yl; Preferably, R3 is hydrogen or methyl; most preferably, R3 is hydrogen.

[0103] A further preferred group of compounds according to this embodiment are compounds of formula (I-2), compounds of formula (I-2-1), wherein: R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N or CH; X is S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, cyclopropyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, or -N(R4)COR5, in each of which R4 is independently hydrogen or methyl, and R5 is methyl, ethyl, or cyclopropyl; and R3 is hydrogen or methyl.

[0104] A further preferred group of compounds according to this embodiment are compounds of formula (I-2-2), which are compounds of formula (I-2-1), wherein: Q1 is hydrogen, cyclopropyl, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0105] A further preferred group of compounds according to this embodiment are compounds of formula (I-2-3), which are compounds of formula (I-2-1), wherein: Q1 is hydrogen, cyclopropyl, N-linked triazolyl, or C-linked pyrimidinyl.

[0106] A further preferred group of compounds according to this embodiment are compounds of formula (I-2-4), which are compounds of formula (I-2-1), wherein: Q1 is hydrogen, cyclopropyl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0107] A further preferred group of compounds according to this embodiment are compounds of formula (I-2), namely compounds of formula (I-2-5), wherein: R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy, preferably R2 is -CF3, -OCF3 or -OCHF2; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; A is N; X is SO2; R1 is ethyl; Q1 is hydrogen, cyclopropyl, 1,2,4-triazol-1-yl or pyrimidin-2-yl; and R3 is hydrogen.

[0108] A further preferred group of compounds according to this embodiment are compounds of formula (I-2-6), which are compounds of formula (I-2-5), wherein: G is CH; X1 is O; and R7 is hydrogen or methyl, preferably hydrogen.

[0109] A further preferred group of compounds according to this embodiment are compounds of formula (I-2-7), which are compounds of formula (I-2-5), wherein: G is N; X1 is O; and R7 is hydrogen or methyl, preferably hydrogen.

[0110] A notable group of compounds according to the invention is represented by formula I-3 [ka] (In the formula, R2 is C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy, preferably R2 is -CF3, -OCF3 or -OCHF2; G is CH or N; X1 is O, S or NCH3; R7 is hydrogen or methyl; Q' is a group of the formulas Qa1 and Qb1 [ka] (wherein the arrow indicates the point of attachment to the bicyclic ring; and, Q1 is N-linked pyrazolyl, which may be monosubstituted with hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, 2-pyridyloxy, chloro, cyano, or trifluoromethyl; or Q1 is N-linked triazolyl, C-linked pyrimidinyl, or -N(R4)COR5, where R4 is hydrogen or methyl and R5 is methyl, ethyl, or cyclopropyl. or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-3.

[0111] A further notable group of compounds according to this embodiment are compounds of formula (I-3), compounds of formula (I-3-1), wherein: Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 2-pyridyloxy, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0112] A further notable group of compounds according to this embodiment are compounds of formula (I-3), namely compounds of formula (I-3-2), wherein: Q1 is hydrogen, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, N-linked triazolyl, or C-linked pyrimidinyl.

[0113] A further notable group of compounds according to this embodiment are compounds of formula (I-3), compounds of formula (I-3-3), wherein: Q1 is hydrogen, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0114] A further notable group of compounds according to this embodiment are compounds of formula (I-3-4), which are compounds of formula (I-3-3), wherein: G is CH; X1 is O; and R7 is hydrogen or methyl, preferably hydrogen.

[0115] A further notable group of compounds according to this embodiment are compounds of formula (I-3-5), which are compounds of formula (I-3-3), wherein: G is N; X1 is O; and R7 is hydrogen or methyl, preferably hydrogen.

[0116] The compounds of the present invention may have any number of benefits, including, inter alia, advantageous levels of biological activity for protecting plants against insects, or excellent properties for use as agrochemical active ingredients (e.g., high biological activity, advantageous activity spectrum, high safety profile, improved physicochemical properties, or high biodegradability or environmental profile). In particular, it has been unexpectedly found that certain compounds of formula (I) may exhibit advantageous safety profiles against non-target arthropods, particularly pollinators such as honeybees, solitary bees, and bumblebees. Most particularly, the European honeybee (Apis mellifera).

[0117] In another aspect, the present invention provides compositions comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), as defined in embodiments by compounds of formulae (I-1), (I-2) and (I-3) (above), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, and, optionally, an adjuvant or diluent.

[0118] In a further aspect, the present invention provides a method for combating and controlling insects, acaridae, nematodes or molluscs, which method comprises applying to the pest, the pest's habitat or plants susceptible to attack by the pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), as defined in any of the embodiments of the compounds of formulae (I-1), (I-2) and (I-3) (above), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, or a composition as defined above.

[0119] In a further aspect, the present invention provides a method for protecting plant propagation material from attack by insects, mites, nematodes or mollusks, comprising the step of treating the propagation material or the site where the propagation material is to be planted with a composition as defined above.

[0120] The process according to the present invention for preparing compounds of formula I is carried out in principle by methods known to those skilled in the art. More specifically, and as shown in Schemes 1 and 2, the subgroup of compounds of formula I in which X is SO (sulfoxide) and / or SO (sulfone) can be obtained by oxidation of the corresponding sulfide compounds of formula I in which X is S, using reagents such as metachloroperbenzoic acid (mCPBA), hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite, or other oxidizing agents such as tert-butyl hypochlorite. This oxidation reaction is generally carried out in the presence of a solvent. Examples of solvents used in this 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 oxidizing agent used in this reaction is generally 1 to 3 moles, preferably 1 to 1.2 moles, per mole of sulfide compound I to produce sulfoxide compound I, and preferably 2 to 2.2 moles per mole of sulfide compound I to produce sulfone compound I. Such an oxidation reaction is disclosed, for example, in WO 2013 / 018928.

[0121] Scheme 1 (all substituents are as defined in Formula I) [ka] The chemistry described above in Scheme 1 for obtaining compounds of formulae I-a2 and I-a3 from compounds of formula I-a1 is equally applicable to the preparation of compounds of formulae I-a5 and I-a6 from compounds of formula I-a4 (Scheme 2), where all previously described substituent definitions remain valid.

[0122] Scheme 2 [ka] A subgroup of compounds of formula I (wherein R2, G, X1 and R7 are as defined in formula I, and Q is defined as Qa, where Q1, R3, X, A and R1 are as defined in formula I) may be defined as compounds of formula I-Qa.

[0123] Scheme 3 [ka] Such compounds of formula I-Qa can be prepared, for example, by reacting a compound of formula II-Qa (wherein Q1, R3, X, A and R1 are as defined in formula I and Xa is a leaving group such as, for example, chlorine, bromine or iodine, or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid) with a compound of formula III (wherein R2, G, X1 and R7 are as defined in formula I and Ya is, for example, B(OH)2 or B(OR b1 )2(wherein, R b1 can be a C1-C4 alkyl group, or two groups OR b1 The compound can be prepared by a Suzuki cross-coupling reaction involving the reaction of a boron-derived functional group such as (wherein, together with the boron atom, may form a five-membered ring, e.g., a boronic acid pinacol ester) with 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. Such Suzuki reactions are well known to those skilled in the art and are reviewed, for example, in J. Orgmet. Chem. 576, 1999, pp. 147-168.

[0124] Alternatively, compounds of formula I-Qa can be prepared by a Stille cross-coupling reaction between a compound of formula III (wherein Ya is a trialkyltin derivative, preferably tri-n-butyltin) and a compound of formula II-Qa (wherein Xa is a leaving group such as chlorine, bromine, or iodine, or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid). Such Stille reactions are typically carried out in the presence of a palladium catalyst, such as tetrakis(triphenylphosphine)-palladium(0) or (1,1'-bis(diphenylphosphino)-ferrocene)dichloropalladium-dichloromethane (1:1 complex), in an inert solvent such as DMF, acetonitrile, or dioxane, optionally in the presence of an additive such as cesium fluoride or lithium chloride, and optionally in the presence of a further catalyst, such as copper(I) iodide. Such Stille couplings are also well known to those skilled in the art and are 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.

[0125] Compounds of formula III, wherein R, G, X, and R are as defined in formula I, and Ya is, for example, B(OH) or B(OR b1 )2(wherein, R b1 can be a C1-C4 alkyl group, or two groups OR b1 can be combined with the boron atom to form a five-membered ring, e.g., boronic acid pinacol ester). Scheme 4 [ka] can be prepared by reacting a compound of formula IV, where R, G, X, and R are as defined in formula I, and X is a leaving group such as chlorine, bromine, or iodine, under boronation conditions detailed in Scheme 5 (Scheme 4).

[0126] Alternatively, compounds of formula III (wherein R2, G, X1 and R7 are as defined in formula I and Ya is a trialkyltin derivative, preferably tri-n-butyltin) can be prepared, for example, by reacting a compound of formula IV with an organometallic species, such as an organomagnesium compound (e.g. isopropylmagnesium chloride), to produce an intermediate species via metal-halogen exchange, preferably carried out in an anhydrous aprotic solvent such as tetrahydrofuran, preferably at low temperatures between −78° C. and 0° C., followed by a stannylation step in which the intermediate species is quenched with a tin reagent of formula (alkyl)3SnCl, such as tri-n-butyltin chloride (n-butyl)3SnCl.

[0127] Similarly, compounds of formula IIIa (a subgroup of compounds of formula III) wherein R2, G, X1 and R7 are as defined in formula I and Ya is B(OR b1 )2, where R b1 is a C1-C4 alkyl group) Scheme 5 [ka] is prepared by reacting a compound of formula IV (wherein R2, G, X1, and R7 are as defined in formula I, and Xb is a leaving group such as, for example, chlorine, bromine, or iodine) with an organometallic species, for example, an organomagnesium compound (e.g., isopropylmagnesium chloride or isopropylmagnesium chloride lithium chloride complex), via metal-halogen exchange, which is preferably carried out in an anhydrous aprotic solvent such as tetrahydrofuran, preferably at low temperatures, preferably between −78° C. and 0° C., to produce an intermediate species of formula B (OR b1 ) 3 of a trialkyl borate reagent (wherein R b1is a C1-C4 alkyl group) (Scheme 5). Depending on the nature of the trialkyl borate, the reaction conditions, and the work-up conditions, dialkylboronates IIIa can be formed and isolated, or boronic acid compounds of formula IIIc (another subgroup of compounds of formula III), where R2, G, X1, and R7 are as defined in formula I, can be obtained directly. Such conditions are described in the literature, for example in WO 2017 / 122722.

[0128] Compounds of formula IIIb (a further subgroup of compounds of formula III) wherein R2, G, X1 and R7 are as defined in formula I and Ya is a boronic acid pinacol ester (also known as a Bpin group) which is a boronic acid pinacol ester having two groups OR b1 (wherein R, G, X, and R are as defined in Formula I, and X is a leaving group such as chlorine, bromine, or iodine) can be prepared by reacting a compound of Formula IV with a bis(pinacolato)diborane of Formula V under palladium-catalyzed reaction conditions. Typically, such conditions involve 1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (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 are described in the literature, for example, in Bioorg. Med. Chem. 15, 7138-7143 (2007). Depending on the reaction and workup conditions, the boronic acid pinacol ester IIIb can be formed in situ, directly affording the boronic acid compound of formula IIIc. Such conditions are described in the literature, for example, in Chem. Pharm. Bull. 68(8):797-801 (2020).

[0129] The hydrolysis of either the compound of formula IIIa or the compound of formula 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 of 0 to 40°C, even more preferably about 10 to 30°C.

[0130] Compounds of Formula II-Qa, wherein Q1, R3, X, A, and R1 are as defined in Formula I, and Xa is a leaving group such as chlorine, bromine, or iodine. Scheme 6 [ka] can be prepared by reacting a compound of Formula VI-Qa (where Q1, R3, X, A, and R1 are as defined in Formula I) with a nitrite such as tert-butyl nitrite t-BuONO or isoamyl nitrite (examples of non-aqueous conditions) or sodium nitrite in the presence of a hydrohalic acid HXa and a copper salt Cu(I)Xa (where Xa is a leaving group such as chlorine, bromine, or iodine) in water (aqueous conditions) under Sandmeyer-type reaction conditions (Scheme 6). This transformation is preferably carried out in an inert solvent such as acetonitrile, a halogenated solvent such as 1,2-dichloroethane or 1,2-dibromoethane (non-aqueous conditions), or water, at a temperature between 0 and 150°C, preferably between room temperature and the boiling point of the reaction mixture.

[0131] Alternatively, a compound of formula II-Qa (wherein X is S and Q1, R3, A and R1 are as defined in formula I and Xa is a leaving group such as, for example, chlorine, bromine or iodine, or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid) can be reacted with a compound of formula VII-Qa (wherein Q1, R3 and A are as defined in formula I and Xa is a leaving group such as, for example, chlorine, bromine or iodine, or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid) and a reagent of formula VIII R1-SH(VIII) or a salt thereof (wherein R1 is as defined in Formula I), optionally in the presence of an alkali metal carbonate such as sodium carbonate or potassium carbonate, an alkali metal hydride such as sodium hydride, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, or a suitable base such as sodium or potassium tert-butoxide, in an inert solvent, preferably at a temperature of 25 to 120°C. Examples of solvents that can 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 the compound of Formula VIII include compounds of Formula VIIIa R1-SM(VIIIa) (wherein R1 is as defined above and M is, for example, sodium or potassium). Such processes for preparing compounds of formula VIII can be found, for example, in WO 16 / 091731.

[0132] Alternatively, this reaction to form II-Qa 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 an inert solvent such as xylene at a temperature between 100 and 160°C, preferably 140°C, as described in Tetrahedron 2005, 61, 5253-5259.

[0133] Oxidation of a compound of formula II-Qa (wherein X is S and Q1, R3, A and R1 are as defined in formula I, and Xa is a leaving group such as, for example, chlorine, bromine or iodine, or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid) to a compound of formula II-Qa (wherein X is SO or SO2) with a suitable oxidizing agent can be achieved under the conditions already described above.

[0134] Certain compounds of formula II-Qa (wherein Q1, R3, X, A, and R1 are as defined in formula I, and Xa is a leaving group such as chlorine) are known and are described in WO 2019 / 131587. Other compounds of formula II-Qa can be prepared analogously to the preparation instructions found therein.

[0135] Certain compounds of formula VI-Qa (wherein Q1, R3, X, A, and R1 are as defined in formula I) are known and are described in WO 2020 / 174094. Other compounds of formula VI-Qa can be prepared analogously to the preparation instructions found therein or by methods known to those skilled in the art.

[0136] Compounds of formula VII-Qa, wherein Q, R and A are as defined in formula I, and X is a leaving group such as, for example, chlorine, bromine or iodine, or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid, and X is a leaving group such as, for example, fluoro or nitro; and Reagents of formula VIII and VIIIa or salts thereof, wherein R1 is as defined in formula I. are all known, commercially available, or can be prepared by methods known to those skilled in the art.

[0137] A compound of formula IV, wherein R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl, and Xb is a leaving group such as, for example, chlorine, bromine, or iodine. Scheme 7 [ka] is a compound of formula IX, wherein R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl, and an electrophilic halogen source Xb + They can be prepared by reacting them with a reagent (e.g., bromine Br2, N-bromosuccinimide NBS, iodine I2, or t-butyl hypochlorite tBuOCl, in particular) (wherein Xb is chlorine, bromine, or iodine) in an inert solvent such as dichloromethane, chloroform, acetonitrile, dimethylacetamide, methanol, ethanol, or pyridine at a temperature of 0 to 50°C (Scheme 7).

[0138] A compound of formula IX (wherein R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl) can be prepared by reacting a compound of formula X (wherein R2, G, and X1 are as defined in formula I) with a reagent of formula XI (wherein R7 is hydrogen or C1-C4 alkyl) under heated conditions, optionally in the presence of a diluent such as N,N-dimethylformamide, dimethylacetamide, toluene, or xylene, at a temperature of 50 to 180°C, preferably from 80°C to the boiling point of the reaction mixture. Typically, the reagent of formula XI is, for example, N,N-dimethylformamide dimethylacetal DMF-DMA (wherein R7 is H) or 1,1-dimethoxy-N,N-dimethyl-ethanamine (wherein R7 is methyl), which are commercially available or can be prepared according to known procedures. Such conditions (for both steps in Scheme 7) are 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).

[0139] Alternatively, a compound of formula IV, wherein R, G, X, and R are as defined in formula I, and X is a leaving group such as, for example, chlorine, bromine, or iodine. Scheme 8 [ka] can be prepared by carrying out a halogenation reaction on a compound of formula XII, where R2, G, X1, and R7 are as defined in formula I (Scheme 8). Preferably, when R7 is hydrogen or C1-C4 alkyl, suitable conditions may involve the formation of an enaminoketone intermediate by reacting a compound of formula XII with pyrrolidine or piperidine in an alcohol (such as methanol or ethanol) at a temperature ranging from 30 to 100°C, preferably from 60°C to the boiling point of the reaction mixture. Subsequent treatment of the enaminoketone intermediate with a halogenating reagent of formula (Xb)2, where Xb is chlorine, bromine, or iodine, in an inert solvent (such as chloroform) at a temperature ranging from 0 to 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 producing compounds of formula IV, for example, by reacting compounds of formula XII with hydrohalic acids 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 oxidizing agent in an inert solvent such as dichloromethane or N,N-dimethylformamide at a temperature of 0-40°C. Other oxidative halogenation conditions can include the use of ceric ammonium nitrate (CAN) and iodine (Xb is iodine) in an inert solvent (e.g., acetonitrile) at temperatures between 50 and 90 °C, as described in Tetrahedron Letters 72 (2021) article 153070 (https: / / doi.org / 10.1016 / j.tetlet.2021.153070).

[0140] Compounds of formula XII (wherein R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl) can be prepared by cyclizing compounds of formula XIII (wherein R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl, and Ra 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 a mixture thereof) at a temperature of 0 to 100° C., preferably room temperature to 80° C. Such conditions are described in the literature, for example, in J. Med. Chem. 33, 1859-1865 (1990). In the particular situation where Ra is C1-C4 alkyl, cyclization can be achieved using potassium carbonate, optionally in catalytic amounts, in an inert solvent such as N,N-dimethylformamide or dimethylacetamide at temperatures between 80 and 180°C, as described in Organic Letters 14, 2710-2713 (2012).

[0141] Compounds of formula XIII (wherein R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl, and Ra is hydrogen or C1-C4 alkyl). Scheme 9 [ka] can typically be prepared by Claisen condensation chemistry from starting materials of formula X-1 or XIV under conditions known to those skilled in the art (Scheme 9). For example, compounds of formula XIII can be prepared by reacting compounds of formula R7C(O)OR2 with compounds of formula R7C(O)OR2 in the presence of a base such as sodium hydride, sodium methoxide, sodium ethoxide, or potassium t-butoxide in an inert solvent such as tetrahydrofuran, diethyl ether, or t-butyl ethyl ether. b wherein R7 is hydrogen or C1-C4 alkyl, and R bis C1-C4 alkyl (preferably methyl or ethyl)). The compounds of formula X above (Scheme 7) constitute a particular subgroup of compounds of formula X-1 in which Ra is hydrogen.

[0142] Alternatively, compounds of formula XIII can be prepared by reacting a compound of formula R7C(O)CH3 or a compound of formula R7C(O)CH2C(O)R under conditions similar to those described above or under conditions appropriately selected by one skilled in the art. d wherein R7 is hydrogen or C1-C4 alkyl, and R d is methyl or C1-C4 alkoxy (preferably methoxy or ethoxy)), wherein R2, G and X1 are as defined in formula I, and Ra is hydrogen or C1-C4 alkyl, and R c can be obtained by condensation with chloro or C1-C4 alkoxy (preferably methoxy or ethoxy). Such conditions are described in the literature, for example, in J. Med. Chem. 33, 1859-1865 (1990).

[0143] Compounds of formula X-1, where R2, G, and X1 are as defined in formula I, and Ra is hydrogen or C1-C4 alkyl (including compounds of formula X, where R2, G, and X1 are as defined in formula I); and A compound of formula XIV, wherein R2, G, and X1 are as defined in formula I, and Ra is hydrogen or C1-C4 alkyl, and R c is chloro or C1-C4 alkoxy (preferably methoxy or ethoxy) are known, commercially available, or can be prepared by methods known to those skilled in the art.

[0144] A subgroup of compounds of formula I (wherein R2, G, X1 and R7 are as defined in formula I, and Q is defined as Qb, where Q1, R3, X, A and R1 are as defined in formula I) may be defined as compounds of formula I-Qb.

[0145] Scheme 10 [ka] The chemistry described above in Scheme 3 for obtaining compounds of formula I-Qa from compounds of formula III and compounds of formula II-Qa is equally applicable to the preparation of compounds of formula I-Qb from compounds of formula III and compounds of formula II-Qb (Scheme 10), where all previously described substituent definitions remain valid.

[0146] The chemistry previously described in Scheme 6 for obtaining compounds of formula II-Qa from either compounds of formula VI-Qa or compounds of formula VII-Qa is equally applicable to the preparation of compounds of formula II-Qb from either compounds of formula VI-Qb or compounds of formula VII-Qb (Scheme 11), where all previously described substituent definitions remain valid.

[0147] Scheme 11 [ka] Alternatively, compounds of formula I-Qb (wherein Q1, R3, X, A, R1, R2, G, X1, and R7 are as defined in formula I) can be prepared as illustrated in Scheme 12.

[0148] Scheme 12 [ka] (a) Suzuki reaction: Pd catalyst (e.g., Pd(PPh3)4 or Pd(dppf)Cl2), base (e.g., Na2CO3), solvent (e.g., 1,2-dimethoxyethane / water), 25-180°C. (b) Stille reaction: Pd catalyst (e.g., Pd(PPh3)4 or Pd(PPh3)Cl2), solvent (e.g., toluene), 25-180°C. (c) C-N bond formation: any base (e.g., K2CO3 or Cs2CO3), optionally in the presence of a copper or palladium catalyst, any additive (e.g., N,N'-dimethylethylenediamine), any ligand (e.g., Xantphos), solvent (e.g., dioxane, pyridine, or N,N-dimethylformamide (DMF)), 25-180°C.

[0149] In certain circumstances in Scheme 12, when Q1 is an optionally substituted triazole bonded to a ring containing group A via a ring nitrogen atom, compounds of formula I-Qb (wherein X is SO or SO2) can be converted to compounds of formula XVb (wherein R3, X, A, R1, R2, G, X1 and R7 are as defined in formula I above, and X is SO or SO2, and Xd is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid). group) with an optionally substituted triazole Q1-H (containing a suitable NH functionality) (XVIaa), where Q1 is an N-linked triazolyl, optionally in the presence of an additional base such as potassium carbonate K2CO3 or cesium carbonate Cs2CO3, and optionally in the presence of a copper catalyst, for example copper(I) iodide, at a temperature between 30 and 180°C, optionally under microwave irradiation (CN bond formation).

[0150] In certain circumstances in Scheme 12, when Q1 is -N(R4)COR5 (wherein R4 and R5 are as defined in Formula I), compounds of formula I-Qb (wherein X is SO or SO2) can be prepared from compounds of formula XVb (wherein R3, X, A, R1, R2, G, X1 and R7 are as defined in Formula I above, and X is SO or SO2, and Xd is a leaving group such as, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid) by reaction (CN bond formation) with a reagent Q1-H(XVIaa) which is equivalent to HN(R4)COR5 (wherein R4 and R5 are as defined in Formula I). Such reactions can be carried out in the presence of a base such as potassium carbonate, cesium carbonate, sodium hydroxide, or the like, in an inert solvent such as toluene, dimethylformamide (DMF), N-methylpyrrolidine (NMP), dimethyl sulfoxide (DMSO), dioxane, tetrahydrofuran (THF), or the like, optionally with, for example, palladium(II) acetate, bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) or tris(dibenzylideneacetone)-dipalladium(0) (Pd2(dba)3, optionally in the form of the chloroform adduct), or, for example, tert-BuBrettPhos Pd G3 [(2-di-tert-butylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate or BrettPhos Pd In the presence of a catalyst, such as a palladium precatalyst, for example G3[(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate, and optionally in the presence of a ligand, for example SPhos, t-BuBrettPhos or Xantphos, the reaction is carried out at a temperature of 60-120°C, optionally under microwave irradiation.

[0151] In certain circumstances in Scheme 12, when Q1 is -N(R4)2 (wherein R4 is as defined in Formula I), compounds of formula I-Qb (wherein X is SO or SO2) can be prepared from compounds of formula XVb (wherein R3, X, A, R1, R2, G, X1 and R7 are as defined in Formula I above, and X is SO or SO2, and Xd is a leaving group such as, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid) by reaction (CN bond formation) with a reagent Q1-H(XVIaa) equivalent to HN(R4)2 or a salt thereof (such as a hydrohalide, preferably hydrochloride, or hydrobromide, or trifluoroacetate, or any other equivalent salt) (wherein R4 is as defined in Formula I). Such reactions are typically carried out in inert solvents such as alcohols, amides, esters, ethers, nitriles and water, particularly preferably methanol, ethanol, 2,2,2-trifluoroethanol, propanol, isopropanol, N,N-dimethylformamide, N,N-dimethylacetamide, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, ethyl acetate, toluene, water or mixtures thereof, at temperatures between 0 and 150°C, optionally under microwave irradiation or under pressure in an autoclave, optionally in the presence of a copper catalyst such as copper powder, copper(I) iodide or copper sulfate (optionally in the form of a hydrate) or mixtures thereof, optionally in the presence of a ligand such as, for example, a diamine ligand (for example, N,N'-dimethylethylenediamine or trans-cyclohexyldiamine) or dibenzylideneacetone (dba) or 1,10-phenanthroline, and optionally in the presence of a base such as potassium phosphate.

[0152] The reagents HN(R4)2 or HN(R4)COR5 (wherein R4 and R5 are as defined in Formula I) are known, commercially available, or can be prepared by methods known to those skilled in the art.

[0153] Alternatively, a compound of formula I-Qb (wherein X is SO or SO) can be prepared by reacting a compound of formula XVb (wherein R, X, A, R, R, G, X and R are as defined in formula I above, and X is SO or SO, and X is a leaving group such as, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid) with a compound of formula (XVI) (wherein Q is as defined in formula I and Y b1 is, for example, B(OH)2 or B(OR b1 )2(wherein, R b1 can be a C1-C4 alkyl group, or two groups OR b1 can be a boron-derived functional group such as (R)( ... The reaction temperature can be preferably in the range of room temperature to the boiling point of the reaction mixture, or the reaction can be carried out under microwave irradiation. Such Suzuki reactions are well known to those skilled in the art and are reviewed, for example, in J. Organomet. Chem. 576, 1999, 147-168.

[0154] Alternatively, a compound of formula I-Qb, wherein X is SO or SO, can be prepared by reacting a compound of formula (XVIa), wherein Q is as defined above and Y b2 is a trialkyltin derivative, preferably tri-n-butyltin or tri-methyltin, with a compound of formula XVb (wherein R, X, A, R, R, G, X, and R are as defined in formula I above, and X is SO or SO, and X is a leaving group such as chlorine, bromine, or iodine (preferably chlorine or bromine), or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid). Such a Stille reaction is typically carried out in the presence of a palladium catalyst, such as tetrakis(triphenylphosphine)palladium(0) or bis(triphenylphosphine)palladium(II) dichloride, in an inert solvent such as N,N-dimethylformamide, acetonitrile, toluene, or dioxane, optionally in the presence of an additive such as cesium fluoride or lithium chloride, and optionally in the presence of a further catalyst, such as copper(I) iodide. Such Stille couplings are also well known to those skilled in the art and are 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.

[0155] When Q1 is a 5-membered aromatic ring system bonded to the ring containing the substituent A via a ring nitrogen atom, compounds of formula I-Qb (wherein X is SO or SO2) can be prepared from compounds of formula XVb (wherein R3, X, A, R1, R2, G, X1 and R7 are as defined in formula I above, and X is SO or SO2, and Xd is a leaving group such as, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid) by reaction with potassium carbonate K2CO3 or cesium carbonate. It can be prepared by reaction with a heterocycle Q1-H (containing a suitable NH function) (XVIaa), where Q1 is as defined above, in the presence of a base such as Cs2CO3, optionally in the presence of a copper catalyst, for example copper(I) iodide, with or without an additive such as L-proline, N,N'-dimethylcyclohexane-1,2-diamine or N,N'-dimethyl-ethylene-diamine, in an inert solvent such as N-methylpyrrolidone NMP or N,N-dimethylformamide DMF, at a temperature between 30 and 150°C, optionally under microwave irradiation.

[0156] Oxidation of a compound of formula XVb (wherein R, X, A, R, R, G, X and R are as defined in formula I above, and X is S and X is a leaving group such as, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid) with a suitable oxidizing agent to a compound of formula XVb (wherein X is SO or SO) can be achieved under the conditions already described above.

[0157] Many compounds of formula (XVI), (XVIa) and (XVIaa) are commercially available or can be prepared by one skilled in the art.

[0158] Alternatively, compounds of formula I-Qb (where X is SO or SO) can be prepared from compounds of formula XVb (where X is S (sulfide)) using the same chemistry as above but by changing the order of steps (i.e., XVb (X is S) to I-Qb (X is S) via Suzuki, Stille, or C-N bond formation, followed by an oxidation step to form I-Qb (X is SO or SO)).

[0159] The chemistry previously described in Scheme 12 for obtaining compounds of formula I-Qb from compounds of formula XVb is equally applicable to the preparation of compounds of formula I-Qa from compounds of formula XVa (Scheme 13), where all previously described substituent definitions remain valid.

[0160] Scheme 13 [ka] (a) Suzuki reaction: Pd catalyst (e.g., Pd(PPh3)4 or Pd(dppf)Cl2), base (e.g., Na2CO3), solvent (e.g., 1,2-dimethoxyethane / water), 25-180°C. (b) Stille reaction: Pd catalyst (e.g., Pd(PPh3)4 or Pd(PPh3)Cl2), solvent (e.g., toluene), 25-180°C. (c) C-N bond formation: any base (e.g., K2CO3 or Cs2CO3), optionally in the presence of a copper or palladium catalyst, any additive (e.g., N,N'-dimethylethylenediamine), any ligand (e.g., Xantphos), solvent (e.g., dioxane, pyridine, or N,N-dimethylformamide (DMF)), 25-180°C.

[0161] Alternatively, a compound of formula I, wherein Q, R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl. Scheme 14 [ka] can be prepared by reacting a compound of formula XVIII (wherein Q (in this Scheme 14, the arrows in each of Qa and Qb indicate the point of attachment to the carbon atom ortho to the carbonyl group), R2, G and X1 are as defined in formula I) with a reagent of formula XI (wherein R7 is hydrogen or C1-C4 alkyl) under conditions similar to those already described in Scheme 7 for the conversion of a compound of formula X to a compound of formula IX (Scheme 14). Typically, the reagent of formula XI is, for example, N,N-dimethylformamide dimethyl acetal DMF-DMA (where R7 is H) or 1,1-dimethoxy-N,N-dimethyl-ethanamine (where R7 is methyl). Process XVIII+XI under such conditions allows the direct formation of compounds of formula I without isolation of the intermediate compound of formula XVII that may be formed (wherein Q, R2, G and X1 are as defined in formula I and R7 is hydrogen or C1-C4 alkyl). Such cyclization conditions are described in the literature, for example in WO 2015 / 047113.

[0162] Similarly, a compound of formula I, wherein Q, R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl, can be reacted with a compound of formula XVIII, wherein Q, R2, G, and X1 are as defined in formula I, and a reagent of formula XIX, wherein R7 is hydrogen or C1-C4 alkyl, and R f is C1-C4 alkyl) preferably in the presence of an additive (optionally in catalytic amount) 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 ranging from 50 to 180°C, preferably from 80°C to the boiling point of the reaction mixture (Scheme 14). Typically, the reagent of formula XIX can be prepared by reacting, for example, triethyl orthoformate (where R7 is H and R fis ethyl). Under such conditions, process XVIII+XIX can produce an intermediate compound of formula XX (wherein Q, R2, G, and X1 are as defined in formula I, R7 is hydrogen or C1-C4 alkyl, and R f This allows for the direct production of the compound of formula I without the isolation of the aryl group (wherein is C1-C4 alkyl). Such cyclization conditions are described in literature, for example, J. Chem Research (12), 683-685 (2008).

[0163] Alternatively, a compound of formula I, wherein Q, R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl. Scheme 15 [ka] can be prepared by cyclizing a compound of formula XXI (wherein Q (in this Scheme 15, the arrows in each of Qa and Qb indicate the point of attachment to the carbon atom ortho to the carbonyl group), R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl, and Ra is hydrogen or C1-C4 alkyl) under conditions similar to those already described in Scheme 8 for the conversion of a compound of formula XIII to a compound of formula XII (Scheme 15). Other such cyclization conditions are also described in the literature, for example in WO 2007 / 065888 or Eur. J. Org. Chem. 2971-2983 (2019).

[0164] A compound of formula XVIII, wherein Q (in this Scheme 18, the arrows in each of Qa and Qb indicate the point of attachment to the carbon atom ortho to the carbonyl group), R2, G, and X1 are as defined in formula I. Scheme 16 [ka] can be prepared by dealkylation of compounds of formula XVIII-1 (wherein Q, R2, G, and X1 are as defined in formula I, and Ra 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 61, 7917-7928 (2018) (Scheme 16).

[0165] Compounds of formula XVIII-1 (wherein Q, R2, G, and X1 are as defined in formula I, and Ra is hydrogen or C1-C4 alkyl) (including compounds of formula XVIII (wherein Q, R2, G, and X1 are as defined in formula I)) can be synthesized by the reaction of compounds of formula X-1 (wherein R2, G, and X1 are as defined in formula I, and Ra is hydrogen or C1-C4 alkyl) (including compounds of formula X (wherein R2, G, and X1 are as defined in formula I)) with compounds of formula II-Qa or II-Qb (wherein Q1, R3, X, A, and R1 are as defined in formula I). X-1 can be prepared by reacting XVIII-1 with II-Qa (wherein Xa is a leaving group such as, for example, chlorine, bromine, or iodine, or an aryl or alkyl sulfonate such as trifluoromethanesulfonate) in the presence of a base such as potassium carbonate or cesium carbonate, sodium hydride, sodium methoxide, sodium ethoxide, or potassium t-butoxide in an inert solvent such as tetrahydrofuran, t-butyl ethyl ether, acetonitrile, dimethyl sulfoxide, or N,N-dimethylformamide at a temperature ranging from 0 to 80°C, preferably from 20°C to the boiling point of the reaction mixture. Such conditions are described in, for example, Tetrahedron Letters 54, 402-405 (2013). Reaction of X-1 with II-Qa gives XVIII-1, where Q is Qa; similarly, reaction of X-1 with II-Qb gives XVIII-1, where Q is Qb.

[0166] Alternatively, a compound of formula XVIII-1 (wherein Q, R2, G, and X1 are as defined in formula I, and Ra is hydrogen or C1-C4 alkyl) can be prepared by reacting a compound of formula X-1 (wherein R2, G, and X1 are as defined in formula I, and Ra is hydrogen or C1-C4 alkyl) with a compound of formula II-Qa or II-Qb (wherein Q1, R3, X, A, and R1 are as defined in formula I, and Xa is a leaving group such as chlorine, bromine, or iodine, or an aryl- or alkylsulfonate such as trifluoromethanesulfonate), for example, with palladium acetate. The compound can be prepared by reacting the compound in the presence of a catalyst such as palladium(II), palladium(II) chloride, bis(dibenzylideneacetone)palladium(0) (Pd(dba)), or tris(dibenzylideneacetone)-dipalladium(0) (Pd(dba)), optionally in the form of a chloroform adduct, in the presence of a ligand such as triphenylphosphine, BINAP, or xantphos, in the presence of a base such as sodium or potassium t-butoxide, cesium carbonate, or potassium carbonate, in an inert solvent such as tetrahydrofuran, toluene, or dioxane, at a temperature of 60 to 120 °C, optionally under microwave irradiation. Such conditions are described, for example, in WO 2016 / 097073, CN 109956928, or Angew Chem Int Ed 53, 1529-1533 (2014).

[0167] Compounds of formula XXI (wherein Q (in this Scheme 17, the arrows in each of Qa and Qb indicate the point of attachment to the carbon atom ortho to the carbonyl group), R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl, and Ra is hydrogen or C1-C4 alkyl). Scheme 17 [ka] can be prepared by reacting a compound of formula XIII (wherein R2, G, and X1 are as defined in formula I, and R7 is hydrogen or C1-C4 alkyl, and Ra is hydrogen or C1-C4 alkyl) with a compound of formula II-Qa or II-Qb (wherein Q1, R3, X, A, and R1 are as defined in formula I, and Xa is a leaving group such as chlorine, bromine, or iodine, or an aryl- or alkylsulfonate such as trifluoromethanesulfonic acid) in the presence of a base such as lithium diisopropylamide, potassium bis(trimethylsilyl)amide, sodium methoxide, sodium ethoxide, potassium t-butoxide, or sodium hydride, optionally over a copper or palladium catalyst, in an inert solvent such as tetrahydrofuran, t-butyl ethyl ether, or N,N-dimethylformamide, and at a temperature between 0 and 80°C (Scheme 17). Reaction of XIII with II-Qa gives XXI where Q is Qa; similarly, reaction of XIII with II-Qb gives XXI where Q is Qb.

[0168] The reactants can be reacted in the presence of a base. Examples of suitable bases include alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamides, alkylenediamides, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxide and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

[0169] The reactants can be reacted with each other as they are, i.e., without the addition of a solvent or diluent. However, in most cases, it is advantageous to add an inert solvent or diluent or a mixture thereof. When the reaction is carried out in the presence of a base, the base used in excess, such as triethylamine, pyridine, N-methylmorpholine, or N,N-diethylaniline, can also serve as the solvent or diluent.

[0170] The reaction is advantageously carried out in the temperature range of about -80°C to about +140°C, preferably about -30°C to about +100°C, and in many cases in the range of room temperature to about +80°C.

[0171] Compounds of formula I can be converted into other compounds of formula I in a manner known per se by conventional methods by replacing one or more substituents of the starting compound of formula I by other substituents according to the invention, as well as by subsequent modification of the compound by reactions such as oxidation, alkylation, reduction, acylation and other methods known to those skilled in the art.

[0172] Depending on the respective suitable reaction conditions and the choice of starting materials, it is possible, for example, to simply replace one substituent with another substituent according to the invention in one reaction step, or multiple substituents can be replaced with other substituents according to the invention in the same reaction step.

[0173] 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 can be obtained by treatment with a suitable acid or with a suitable ion exchange reagent, and base salts can be obtained by treatment with a suitable base or with a suitable ion exchange reagent.

[0174] Salts of compounds of formula I can be converted in a customary manner into acid addition salts of the free compounds I, for example by treatment with suitable basic compounds or suitable ion exchange reagents, and into salts with bases, for example by treatment with suitable acids or suitable ion exchange reagents.

[0175] Salts of compounds of formula I may be converted into other salts, such as acid addition salts, of compounds of formula I in a manner known per se, for example by treating the inorganic acid salt, such as the hydrochloride, with a suitable metal salt, such as the sodium, barium or silver salt of the acid, for example silver acetate, in a suitable solvent in which the inorganic salt that forms silver chloride is insoluble and therefore precipitates from the reaction mixture.

[0176] Depending on the procedure or reaction conditions, compounds of formula I having salt-forming properties may be obtained in free form or in salt form.

[0177] The compounds of formula I and, where appropriate, their tautomers, can exist in the form of one of the possible isomers or as mixtures thereof, in the form of pure isomers, such as enantiomers and / or diastereomers, or as isomeric mixtures, such as enantiomeric mixtures, such as racemates, diastereomeric mixtures or racemic mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms occurring in the molecule and / or depending on the configuration of non-aromatic double bonds occurring in the molecule, in each case in free form or in salt form; the invention relates to the pure isomers and also to all possible isomeric mixtures, and is to be understood in this sense above and below, respectively, even if details of the stereochemistry are not specifically stated in each case.

[0178] Diastereomeric or racemic mixtures of compounds of formula I, in free or salt form, obtained depending on which starting materials and procedures are selected, can be separated in known manner into pure diastereomers or racemates on the basis of the physical chemical differences of the components, for example, by fractional crystallization, distillation, and / or chromatography.

[0179] Enantiomeric mixtures, such as racemates, obtained in a similar manner can be resolved into their optical antipodes by known methods, for example by recrystallization from optically active solvents, by chromatography on chiral adsorbents, for example by high-performance liquid chromatography (HPLC) on acetylcellulose using suitable microorganisms, by cleavage with specific immobilized enzymes via the formation of inclusion compounds, for example with chiral crown ethers, in which only one enantiomer is complexed, or by conversion to diastereomeric salts, for example by reacting the basic final product racemate with an optically active acid, such as 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 thus obtained, for example by fractional crystallization based on their different solubilities, to give diastereomers from which the desired enantiomer can be released by the action of a suitable substance, for example a basic substance.

[0180] Pure diastereomers or enantiomers can be obtained according to the present invention not only by separating the appropriate isomeric mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, e.g. by carrying out the process according to the present invention using stereochemically characterized starting materials.

[0181] The N-oxides can be prepared by reacting the compounds of formula I with a suitable oxidizing agent, such as the H2O2 / urea adduct, in the presence of an acid anhydride, such as trifluoroacetic anhydride. Such oxidations are known from the literature, for example, J. Med. Chem., 32(12), 2561-73, 1989 or WO 2000 / 15615.

[0182] When the individual components have different biological activities, it may be advantageous to isolate or synthesize the respective more biologically active isomer, e.g., enantiomer or diastereomer, or mixture of isomers, e.g., mixture of enantiomers or diastereomers.

[0183] The compounds of formula I and, where appropriate, their tautomers, may also be obtained in free or salt form, optionally in the form of hydrates, and / or contain other solvents, for example solvents that may have been used for the crystallization of compounds present in solid form.

[0184] In the following, the compounds according to the following Tables A-1 to A-36, Tables B-1 to B-36, Tables C-1 to C-36 and Tables D-1 to D-36 can be prepared according to the above-mentioned methods. The following examples are intended to illustrate the present invention and to show preferred compounds of formula I.

[0185] The following Tables A-1 to A-36 show specific compounds of the present invention. [ka]

[0186] Table A-1 provides 20 compounds A-1.001 to A-1.020 of formula Ia-Qa, where R2 is CF3, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0187] [Table 1]

[0188] In Table Y and in Table A, "cycloC3" represents cyclopropyl.

[0189] For example, compound A-10.018 is [ka] is.

[0190] Table A-2 provides 20 compounds A-2.001 to A-2.020 of formula Ia-Qa, where R2 is CF3, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0191] Table A-3 provides 20 compounds A-3.001 to A-3.020 of formula Ia-Qa, where R2 is CF3, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0192] Table A-4 provides 20 compounds A-4.001 to A-4.020 of formula Ia-Qa, where R2 is CF3, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0193] Table A-5 provides 20 compounds A-5.001 to A-5.020 of formula Ia-Qa, where R2 is CF3, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0194] Table A-6 provides 20 compounds A-6.001 to A-6.020 of formula Ia-Qa, where R2 is CF3, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0195] Table A-7 provides 20 compounds A-7.001 to A-7.020 of formula Ia-Qa, where R2 is CF3, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0196] Table A-8 provides 20 compounds A-8.001 to A-8.020 of formula Ia-Qa, where R2 is CF3, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0197] Table A-9 provides 20 compounds A-9.001 to A-9.020 of formula Ia-Qa, where R2 is CF3, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0198] Table A-10 provides 20 compounds A-10.001 to A-10.020 of formula Ia-Qa, where R2 is CF3, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0199] Table A-11 provides 20 compounds A-11.001 to A-11.020 of formula Ia-Qa, where R2 is CF3, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0200] Table A-12 provides 20 compounds A-12.001 to A-12.020 of formula Ia-Qa, where R2 is CF3, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0201] Table A-13 provides 20 compounds A-13.001 to A-13.020 of formula Ia-Qa, where R2 is OCHF2, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0202] Table A-14 provides 20 compounds A-14.001 to A-14.019 of formula Ia-Qa, where R2 is OCHF2, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0203] Table A-15 provides 20 compounds A-15.001 to A-15.020 of formula Ia-Qa, where R2 is OCHF2, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0204] Table A-16 provides 20 compounds A-16.001 to A-16.020 of formula Ia-Qa, where R2 is OCHF2, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0205] Table A-17 provides 20 compounds A-17.001 to A-17.020 of formula Ia-Qa, where R2 is OCHF2, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0206] Table A-18 provides 20 compounds A-18.001 to A-18.020 of formula Ia-Qa, where R2 is OCHF2, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0207] Table A-19 provides 20 compounds A-19.001 to A-19.020 of formula Ia-Qa, where R2 is OCHF2, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0208] Table A-20 provides twenty compounds A-20.001 to A-20.020 of formula Ia-Qa, where R2 is OCHF2, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0209] Table A-21 provides 20 compounds A-21.001 to A-21.020 of formula Ia-Qa, where R2 is OCHF2, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0210] Table A-22 provides 20 compounds A-22.001 to A-22.020 of formula Ia-Qa, where R2 is OCHF2, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0211] Table A-23 provides 20 compounds A-23.001 to A-23.020 of formula Ia-Qa, where R2 is OCHF2, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0212] Table A-24 provides 20 compounds A-24.001 to A-24.020 of formula Ia-Qa, where R2 is OCHF2, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0213] Table A-25 provides 20 compounds A-25.001 to A-25.020 of formula Ia-Qa, where R2 is OCF3, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0214] Table A-26 provides 20 compounds A-26.001 to A-26.020 of formula Ia-Qa, where R2 is OCF3, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0215] Table A-27 provides 20 compounds A-27.001 to A-27.020 of formula Ia-Qa, where R2 is OCF3, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0216] Table A-28 provides 20 compounds A-28.001 to A-28.020 of formula Ia-Qa, where R2 is OCF3, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0217] Table A-29 provides 20 compounds A-29.001 to A-29.020 of formula Ia-Qa, where R2 is OCF3, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0218] Table A-30 provides 20 compounds A-30.001 to A-30.020 of formula Ia-Qa, where R2 is OCF3, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0219] Table A-31 provides 20 compounds A-31.001 to A-31.020 of formula Ia-Qa, where R2 is OCF3, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0220] Table A-32 provides 20 compounds A-32.001 to A-32.020 of formula Ia-Qa, where R2 is OCF3, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0221] Table A-33 provides 20 compounds A-33.001 to A-33.020 of formula Ia-Qa, where R2 is OCF3, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0222] Table A-34 provides 20 compounds A-34.001 to A-34.020 of formula Ia-Qa, where R2 is OCF3, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0223] Table A-35 provides 20 compounds A-35.001 to A-35.020 of formula Ia-Qa, where R2 is OCF3, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0224] Table A-36 provides 20 compounds A-36.001 to A-36.020 of formula Ia-Qa, where R2 is OCF3, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0225] The following Tables B-1 to B-36 further illustrate specific compounds of the present invention. [ka]

[0226] Table B-1 provides 12 compounds B-1.001 to B-1.012 of formula Ia-Qb, where R2 is CF3, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0227] [Table 2]

[0228] In Table Z and in Table B, "cycloC3" represents cyclopropyl.

[0229] Table B-2 provides 12 compounds B-2.001 to B-2.012 of formula Ia-Qb, where R2 is CF3, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0230] Table B-3 provides 12 compounds B-3.001 to B-3.012 of formula Ia-Qb, where R2 is CF3, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0231] Table B-4 provides 12 compounds B-4.001 to B-4.012 of formula Ia-Qb, where R2 is CF3, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0232] Table B-5 provides 12 compounds B-5.001 to B-5.012 of formula Ia-Qb, where R2 is CF3, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0233] Table B-6 provides 12 compounds B-6.001 to B-6.012 of formula Ia-Qb, where R2 is CF3, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0234] Table B-7 provides 12 compounds B-7.001 to B-7.012 of formula Ia-Qb, where R2 is CF3, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0235] Table B-8 provides 12 compounds B-8.001 to B-8.012 of formula Ia-Qb, where R2 is CF3, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0236] Table B-9 provides 12 compounds B-9.001 to B-9.012 of formula Ia-Qb, where R2 is CF3, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0237] Table B-10 provides 12 compounds B-10.001 to B-10.012 of formula Ia-Qb, where R2 is CF3, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0238] Table B-11 provides 12 compounds B-11.001 to B-11.012 of formula Ia-Qb, where R2 is CF3, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0239] Table B-12 provides twelve compounds B-12.001 to B-12.012 of formula Ia-Qb, where R2 is CF3, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0240] Table B-13 provides twelve compounds B-13.001 to B-13.012 of formula Ia-Qb, where R2 is OCHF2, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0241] Table B-14 provides twelve compounds B-14.001 to B-14.012 of formula Ia-Qb, where R2 is OCHF2, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0242] Table B-15 provides twelve compounds B-15.001 to B-15.012 of formula Ia-Qb, where R2 is OCHF2, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0243] Table B-16 provides 12 compounds B-16.001 to B-16.012 of formula Ia-Qb, where R2 is OCHF2, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0244] Table B-17 provides 12 compounds B-17.001 to B-17.012 of formula Ia-Qb, where R2 is OCHF2, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0245] Table B-18 provides 12 compounds B-18.001 to B-18.012 of formula Ia-Qb, where R2 is OCHF2, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0246] Table B-19 provides 12 compounds B-19.001 to B-19.012 of formula Ia-Qb, where R2 is OCHF2, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0247] Table B-20 provides 12 compounds B-20.001 to B-20.012 of formula Ia-Qb, where R2 is OCHF2, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0248] Table B-21 provides 12 compounds B-21.001 to B-21.012 of formula Ia-Qb, where R2 is OCHF2, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0249] Table B-22 provides 12 compounds B-22.001 to B-22.012 of formula Ia-Qb, where R2 is OCHF2, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0250] Table B-23 provides 12 compounds B-23.001 to B-23.012 of formula Ia-Qb, where R2 is OCHF2, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0251] Table B-24 provides 12 compounds B-24.001 to B-24.012 of formula Ia-Qb, where R2 is OCHF2, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0252] Table B-25 provides 12 compounds B-25.001 to B-25.012 of formula Ia-Qb, where R2 is OCF3, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0253] Table B-26 provides 12 compounds B-26.001 to B-26.012 of formula Ia-Qb, where R2 is OCF3, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0254] Table B-27 provides 12 compounds B-27.001 to B-27.012 of formula Ia-Qb, where R2 is OCF3, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0255] Table B-28 provides 12 compounds B-28.001 to B-28.012 of formula Ia-Qb, where R2 is OCF3, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0256] Table B-29 provides 12 compounds B-29.001 to B-29.012 of formula Ia-Qb, where R2 is OCF3, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0257] Table B-30 provides 12 compounds B-30.001 to B-30.012 of formula Ia-Qb, where R2 is OCF3, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0258] Table B-31 provides 12 compounds B-31.001 to B-31.012 of formula Ia-Qb, where R2 is OCF3, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0259] Table B-32 provides 12 compounds B-32.001 to B-32.012 of formula Ia-Qb, where R2 is OCF3, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0260] Table B-33 provides 12 compounds B-33.001 to B-33.012 of formula Ia-Qb, where R2 is OCF3, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0261] Table B-34 provides 12 compounds B-34.001 to B-34.012 of formula Ia-Qb, where R2 is OCF3, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0262] Table B-35 provides 12 compounds B-35.001 to B-35.012 of formula Ia-Qb, where R2 is OCF3, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0263] Table B-36 provides 12 compounds B-36.001 to B-36.012 of formula Ia-Qb, where R2 is OCF3, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0264] Tables C-1 to C-36 below further illustrate specific compounds of the present invention. [ka]

[0265] In Table Y and in Table C, "cycloC3" represents cyclopropyl.

[0266] Table C-1 provides 20 compounds C-1.001 to C-1.020 of formula Ib-Qa, where R2 is CF3, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0267] Table C-2 provides 20 compounds C-2.001 to C-2.020 of formula Ib-Qa, where R2 is CF3, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0268] Table C-3 provides 20 compounds C-3.001 to C-3.020 of formula Ib-Qa, where R2 is CF3, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0269] Table C-4 provides 20 compounds C-4.001 to C-4.020 of formula Ib-Qa, where R2 is CF3, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0270] Table C-5 provides 20 compounds C-5.001 to C-5.020 of formula Ib-Qa, where R2 is CF3, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0271] Table C-6 provides 20 compounds C-6.001 to C-6.020 of formula Ib-Qa, where R2 is CF3, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0272] Table C-7 provides 20 compounds C-7.001 to C-7.020 of formula Ib-Qa, where R2 is CF3, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0273] Table C-8 provides 20 compounds C-8.001 to C-8.020 of formula Ib-Qa, where R2 is CF3, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0274] Table C-9 provides 20 compounds C-9.001 to C-9.020 of formula Ib-Qa, where R2 is CF3, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0275] Table C-10 provides 20 compounds C-10.001 to C-10.020 of formula Ib-Qa, where R2 is CF3, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0276] Table C-11 provides 20 compounds C-11.001 to C-11.020 of formula Ib-Qa, where R2 is CF3, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0277] Table C-12 provides 20 compounds C-12.001 to C-12.020 of formula Ib-Qa, where R2 is CF3, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0278] Table C-13 provides 20 compounds C-13.001 to C-13.020 of formula Ib-Qa, where R2 is OCHF2, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0279] Table C-14 provides 20 compounds C-14.001 to C-14.020 of formula Ib-Qa, where R2 is OCHF2, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0280] Table C-15 provides 20 compounds C-15.001 to C-15.020 of formula Ib-Qa, where R2 is OCHF2, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0281] Table C-16 provides 20 compounds C-16.001 to C-16.020 of formula Ib-Qa, where R2 is OCHF2, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0282] Table C-17 provides 20 compounds C-17.001 to C-17.020 of formula Ib-Qa, where R2 is OCHF2, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0283] Table C-18 provides 20 compounds C-18.001 to C-18.020 of formula Ib-Qa, where R2 is OCHF2, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0284] Table C-19 provides 20 compounds C-19.001 to C-19.20 of formula Ib-Qa, where R2 is OCHF2, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0285] Table C-20 provides 20 compounds C-20.001 to C-20.020 of formula Ib-Qa, where R2 is OCHF2, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0286] Table C-21 provides 20 compounds C-21.001 to C-21.020 of formula Ib-Qa, where R2 is OCHF2, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0287] Table C-22 provides 20 compounds C-22.001 to C-22.020 of formula Ib-Qa, where R2 is OCHF2, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0288] Table C-23 provides 20 compounds C-23.001 to C-23.020 of formula Ib-Qa, where R2 is OCHF2, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0289] Table C-24 provides 20 compounds C-24.001 to C-24.020 of formula Ib-Qa, where R2 is OCHF2, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0290] Table C-25 provides 20 compounds C-25.001 to C-25.020 of formula Ib-Qa, where R2 is OCF3, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0291] Table C-26 provides 20 compounds C-26.001 to C-26.020 of formula Ib-Qa, where R2 is OCF3, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0292] Table C-27 provides 20 compounds C-27.001 to C-27.020 of formula Ib-Qa, where R2 is OCF3, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0293] Table C-28 provides 20 compounds C-28.001 to C-28.020 of formula Ib-Qa, where R2 is OCF3, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0294] Table C-29 provides 20 compounds C-29.001 to C-29.020 of formula Ib-Qa, where R2 is OCF3, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0295] Table C-30 provides 20 compounds C-30.001 to C-30.020 of formula Ib-Qa, where R2 is OCF3, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0296] Table C-31 provides 20 compounds C-31.001 to C-31.020 of formula Ib-Qa, where R2 is OCF3, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0297] Table C-32 provides 20 compounds C-32.001 to C-32.020 of formula Ib-Qa, where R2 is OCF3, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0298] Table C-33 provides 20 compounds C-33.001 to C-33.020 of formula Ib-Qa, where R2 is OCF3, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0299] Table C-34 provides 20 compounds C-34.001 to C-34.020 of formula Ib-Qa, where R2 is OCF3, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0300] Table C-35 provides 20 compounds C-35.001 to C-35.020 of formula Ib-Qa, where R2 is OCF3, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0301] Table C-36 provides 20 compounds C-36.001 to C-36.020 of formula Ib-Qa, where R2 is OCF3, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0302] Tables D-1 to D-36 below further illustrate specific compounds of the present invention. [ka]

[0303] In Table Z and in Table D, "cycloC3" represents cyclopropyl.

[0304] Table D-1 provides 12 compounds D-1.001 to D-1.012 of formula Ib-Qb, where R2 is CF3, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0305] Table D-2 provides 12 compounds D-2.001 to D-2.012 of formula Ib-Qb, where R2 is CF3, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0306] Table D-3 provides 12 compounds D-3.001 to D-3.012 of formula Ib-Qb, where R2 is CF3, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0307] Table D-4 provides 12 compounds D-4.001 to D-4.012 of formula Ib-Qb, where R2 is CF3, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0308] Table D-5 provides 12 compounds D-5.001 to D-5.012 of formula Ib-Qb, where R2 is CF3, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0309] Table D-6 provides 12 compounds D-6.001 to D-6.012 of formula Ib-Qb, where R2 is CF3, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0310] Table D-7 provides 12 compounds D-7.001 to D-7.012 of formula Ib-Qb, where R2 is CF3, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0311] Table D-8 provides 12 compounds D-8.001 to D-8.012 of formula Ib-Qb, where R2 is CF3, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0312] Table D-9 provides 12 compounds D-9.001 to D-9.012 of formula Ib-Qb, where R2 is CF3, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0313] Table D-10 provides twelve compounds D-10.001 to D-10.012 of formula Ib-Qb, where R2 is CF3, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0314] Table D-11 provides twelve compounds D-11.001 to D-11.012 of formula Ib-Qb, where R2 is CF3, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0315] Table D-12 provides twelve compounds D-12.001 to D-12.012 of formula Ib-Qb, where R2 is CF3, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0316] Table D-13 provides twelve compounds D-13.001 to D-13.012 of formula Ib-Qb, where R2 is OCHF2, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0317] Table D-14 provides twelve compounds D-14.001 to D-14.012 of formula Ib-Qb, where R2 is OCHF2, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0318] Table D-15 provides twelve compounds D-15.001 to D-15.012 of formula Ib-Qb, where R2 is OCHF2, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0319] Table D-16 provides twelve compounds D-16.001 to D-16.012 of formula Ib-Qb, where R2 is OCHF2, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0320] Table D-17 provides twelve compounds D-17.001 to D-17.012 of formula Ib-Qb, where R2 is OCHF2, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0321] Table D-18 provides twelve compounds D-18.001 to D-18.012 of formula Ib-Qb, where R2 is OCHF2, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0322] Table D-19 provides twelve compounds D-19.001 to D-19.012 of formula Ib-Qb, where R2 is OCHF2, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0323] Table D-20 provides twelve compounds D-20.001 to D-20.012 of formula Ib-Qb, where R2 is OCHF2, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0324] Table D-21 provides twelve compounds D-21.001 to D-21.012 of formula Ib-Qb, where R2 is OCHF2, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0325] Table D-22 provides twelve compounds D-22.001 to D-22.012 of formula Ib-Qb, where R2 is OCHF2, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0326] Table D-23 provides twelve compounds D-23.001 to D-23.012 of formula Ib-Qb, where R2 is OCHF2, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0327] Table D-24 provides twelve compounds D-24.001 to D-24.012 of formula Ib-Qb, where R2 is OCHF2, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0328] Table D-25 provides twelve compounds D-25.001 to D-25.012 of formula Ib-Qb, where R2 is OCF3, R7 is H, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0329] Table D-26 provides twelve compounds D-26.001 to D-26.012 of formula Ib-Qb, where R2 is OCF3, R7 is H, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0330] Table D-27 provides twelve compounds D-27.001 to D-27.012 of formula Ib-Qb, where R2 is OCF3, R7 is H, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0331] Table D-28 provides twelve compounds D-28.001 to D-28.012 of formula Ib-Qb, where R2 is OCF3, R7 is H, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0332] Table D-29 provides twelve compounds D-29.001 to D-29.012 of formula Ib-Qb, where R2 is OCF3, R7 is H, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0333] Table D-30 provides twelve compounds D-30.001 to D-30.012 of formula Ib-Qb, where R2 is OCF3, R7 is H, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0334] Table D-31 provides twelve compounds D-31.001 to D-31.012 of formula Ib-Qb, where R2 is OCF3, R7 is CH3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0335] Table D-32 provides twelve compounds D-32.001 to D-32.012 of formula Ib-Qb, where R2 is OCF3, R7 is CH3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0336] Table D-33 provides twelve compounds D-33.001 to D-33.012 of formula Ib-Qb, where R2 is OCF3, R7 is CH3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0337] Table D-34 provides twelve compounds D-34.001 to D-34.012 of formula Ib-Qb, where R2 is OCF3, R7 is CH3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0338] Table D-35 provides twelve compounds D-35.001 to D-35.012 of formula Ib-Qb, where R2 is OCF3, R7 is CH3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0339] Table D-36 provides twelve compounds D-36.001 to D-36.012 of formula Ib-Qb, where R2 is OCF3, R7 is CH3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0340] The compounds of formula I according to the invention are preventively and / or therapeutically useful active ingredients in the field of pest control, even at low application rates, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded animal species, fish, and plants. The active ingredients according to the invention act not only against normally susceptible animal pests, such as insects or representatives of the order Acarina, but also against all or individual developmental stages of resistant animal pests. The insecticidal or acaricidal activity of the active ingredients according to the invention can be manifested directly (i.e., killing of the pest immediately or only after a certain period of time, for example, during molting) or indirectly (e.g., by reducing egg production and / or hatching rate, a good activity corresponding to a killing rate (mortality) of at least 50-60%).

[0341] Examples of the above animal pests are: From the order Acarina, for example: 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. 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.; From the order Anoplura, for example: Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; From the order Coleoptera, for example: 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, Hypothenemus hampei, Lagria vilosa, Leptinotarsa ​​decemLineata, Lissorhoptrus spp., Liogenys spp., Maecolaspis spp., Maladera castanea, Megascelis spp. spp., Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp., Phlyctinus spp., Popillia spp.), Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabaeidae, Sitophilus spp., Sitotroga spp., Somaticus spp., Sphenophorus spp., Sternechus subsignatus, Tenebrio spp., Tribolium spp. and Trogoderma spp.;. From the order Diptera, for example: Aedes spp., Anopheles spp., Antherigona soccata, Bactrocea oleae, Bibio hortulanus, Bradysia spp., Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp., Drosophila melanogaster, Fannia spp. 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. spp.), Rhagoletis spp., Rivelia quadrifasciata, Scatella spp., Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.; From the order Hemiptera, for example: Acanthocoris scabrator, Acrosternum spp., Adelphocoris lineolatus, Amblypelta nitida, Bathycoelia thalassina, Blissus spp., Cimex spp., Clavigrella tomentosicollis, Creontiades spp., Distantiella theobroma, Dichelops furcatus, Dysdercus spp., Edessa spp., Euschistus spp. spp.), Eurydema pulchrum, Eurygaster spp., Brown marmorated stink bugs (Halyomorpha halys), Horcias nobilellus, Leptocorisa spp., Mire bugs (Lygus spp.), Margarodes spp., Murgantia histrionic, Neomegalotomus spp., Nesidiocoris tenuis, Nezara spp., Nysius simulans, Oebalus insularis, Piesma spp. spp.), Piezodorus spp., Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp., Thyanta spp., Triatoma spp.), Vatiga illudens;. Acyrthosium pisum, Adalges spp., Agalliana ensigera, Agonoscena targionii, Aleurodicus spp., Aleurocanthus spp., Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp. spp.), Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp., Brachycaudus spp., Brevicoryne brassicae, Cacopsylla spp., Cavariella aegopodii Scop., Ceroplaster spp.), Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp., Cofana spectra, Cryptomyzus spp., Cicadulina spp., Coccus hesperidum, Dalbulus maidis, Dialeurodes spp., Diaphorina citri, Diuraphis noxia, Dysaphis spp., Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp., Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp., Mahanarva spp., Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp.), Neotoxoptera spp., Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Bayberry whitefly (Parabemisia myricae), Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Corn planthopper (Peregrinus maidis), Perkinsiella spp., Hop wart aphid (Phorodon humuli, Phylloxera spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp., Scaphoideus spp. spp.), Schizaphis spp., Sitobion spp.), Sogatella furcifera, Spisstilus festinus, Tarophagus Proserpina, Toxoptera spp., Trialeurodes spp., Tridiscus sporoboli, Trionymus spp., Trioza erytreae, Unaspis citri, Zygina flammigera, Zyginidia scutellaris; From the order Hymenoptera, for example: Acromyrmex ants, Arge spp., Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis ants, Neodiprion spp., Pogonomyrmex spp., Slenopsis invicta, Solenopsis spp. and Vespa spp.; From the order Isoptera, for example: Coptotermes spp., Corniternes cumulans, Incisitermes spp., Macrotermes spp., Mastotermes spp., Microtermes spp., Reticulitermes spp.; Solenopsis geminate From the order Lepidoptera, for example: Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp., Argyrotaenia spp., Autographa spp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp., Eldana saccharina, Ephestia spp.), Epinotia spp., Estigmene acrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp., Hyphantria cunea, Keiferia lycopersicella lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp., Noctua spp., Operophtera spp., Orniodes indica indica), European corn borer (Ostrinia nubilalis), Pammene spp., Pandemis spp.), pine sawyer moth (Panolis flammea), Papaipema nebris, pink bollworm (Pectinophora gossypiela), coffee leafminer (Perileucoptera coffeella), Pseudaletia unipuncta, potato tuber moth (Phthorimaea operculella), cabbage white butterfly (Pieris rapae), Pieris spp., diamondback moth (Plutella xylostella), Prays spp., Pseudoplusia spp., Rachiplusia nu, Richia albicosta, Scirpophaga spp., Sesamia spp.), Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta and Yponomeuta spp.;. From the order Mallophaga, for example: Damalinea spp. and Trichodectes spp.; From the order Orthoptera, for example: Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscus spp. and Schistocerca spp.; From the order Psocoptera, for example: Liposcelis spp.; From the order Siphonaptera, for example: Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis; From the order Thysanoptera, for example: Calliothrips phaseoli, Frankliniella spp., Heliothrips spp., Hercinothrips spp., Parthenothrips spp., Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp.; From the order Thysanura, for example, Lepisma saccharina.

[0342] The active ingredients according to the invention can be used to control, i.e. suppress or destroy, pests of the above-mentioned types occurring in particular on plants, in particular on useful plants and ornamental plants in agriculture, horticulture and forestry, or on organs such as the fruits, flowers, leaves, stems, tubers or roots of such plants, in some cases even plant organs formed at a later time remaining protected from these pests.

[0343] Suitable target crops are, in particular, cereals such as wheat, barley, rye, oats, rice, maize or sorghum; beets such as sugar beet or fodder beet; fruits, such as pome fruits, stone fruits or soft fruits, for example apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; legumes, such as beans, lentils, peas or soybeans; rapeseed, mustard, poppy, olive, sunflower, palm, castor, cocoa or groundnut. citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes or peppers; plants of the Lauraceae family such as avocado, cinnamon or camphor; and also tobacco, tree nuts, coffee, eggplant, sugarcane, tea, pepper, grapes, hops, plantains and latex plants.

[0344] The compositions and / or methods of the present invention may be used on any ornamental and / or vegetable crop, including flowers, shrubs, broadleaf trees and evergreen trees.

[0345] For example, the present invention relates to the use of the following ornamental species: Ageratum spp., Alonsoa spp., Anemone spp., Anisodontea capsenisis, Anthemis spp., Antirrhinum spp., Aster spp., Begonia spp. (e.g., B. elatior, B. semperflorens, B. tubereux), Bougainvillea spp., Brachycome spp. spp.), Brassica spp. (ornamental), Calceolaria spp., Capsicum annuum, Catharanthus roseus, Canna spp., Centaurea spp., Chrysanthemum spp., Cineraria spp. (C. maritime), Coreopsis spp., Crassula coccinea, Cuphea ignea, Dahlia spp., Delphinium spp., Bleeding hearts spectabilis, Dorotheantus spp., Lisianthus (Eustoma grandiflorum), Forsythia spp., Fuchsia spp., Geranium gnaphalium, Gerbera spp., Globetrotter (Gomphrena globosa), Heliotropium spp., Helianthus spp., Hibiscus spp.), Hortensia spp., Hydrangea spp., Hypoestes phyllostachya, Impatiens spp. (I. Walleriana), Iresines spp., Kalanchoe spp., Lantana camara, Lavatera trimestris, Leonotis leonurus, Lilium spp., Mesembryanthemum spp., Mimulus spp., Monarda spp. spp.), Nemesia spp., Tagetes spp., Dianthus spp. (carnations), Canna spp., Oxalis spp., Bellis spp., Pelargonium spp. (ivy geranium (P. peltatum), P. Zonale), Viola spp. (pansies), Petunia spp., Phlox spp., Plecthranthus spp., Poinsettia spp. spp.), Parthenocissus spp. (American Creeper (P. quinquefolia), Ivy (P. tricuspidata)), Primula spp., Ranunculus spp., Rhododendron spp., Rosa spp. (roses), Rudbeckia spp., Saintpaulia spp., Salvia spp.), Scaevola aemola, Schizanthus wisetonensis, Sedum spp., Solanum spp., Surfinia spp., Tagetes spp., Nicotinia spp., Verbena spp., Zinnia spp., and other bedding plants.

[0346] For example, the present invention relates to the use of the following vegetable species: Allium spp. (garlic (A. sativum), onion (A. cepa), shallot (A. oschaninii), leek (A. porrum), scallion (A. ascalonicum), green onion (A. fistulosum)), chervil (Anthriscus cerefolium), celery (Apium graveolus), asparagus (Asparagus officinalis), beet (Beta vulgarus), Brassica spp. (B. oleracea, Chinese cabbage (B. pekinensis), turnip (B. rapa)), chili pepper (Capsicum annuum), chickpea (Cicer arietinum), endive (Cichorium endivia), Cichorum spp. spp.) (chicory (C. intybus), endive (C. endivia)), watermelon (Citrillus lanatus), Cucumis spp. (saffron (C. sativus), melon (C. melo)), Cucurbita spp. (Cucurbita pepo, Cucurbita maxima), Cyanara spp. (artichoke (C. scolymus), cardoon (C. cardunculus)), carrot (Daucus carota), fennel (Foeniculum vulgare), Hypericum spp., lettuce (Lactuca sativa), tomato spp. spp.) (tomato (L. esculentum), tomato (L. lycopersicum)), mint species (Mentha spp.), basil (Ocimum basilicum), parsley (Petroselinum crispum), Phaseolus species (Phaseolus spp.) (P. vulgaris, runner bean (P.The present invention may be used in any of the following plants: pea (Pisum sativum), radish (Raphanus sativus), rhubarb (Rheum rhaponticum), rosemary (Rosemarinus spp.), salvia (Salvia spp.), yellow rosemary (Scorzonera hispanica), eggplant (Solanum melongena), spinach (Spinacea oleracea), Valerianella spp. (V. locusta, V. eriocarpa), and broad bean (Vicia faba).

[0347] Preferred ornamental species include Saintpaulia, Begonia, Dahlia, Gerbera, Hydrangea, Vervain, Rosa, Kalanchoe, Poinsettia, Aster, Centaurea, Coreopsis, Delphinium, Monarda, Phlox, Rudbeckia, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Salvia, Hydrangea, Rosemary, Sage, St. John's Wort, Mint, Bell Pepper, Tomato, and Cucumber.

[0348] The active ingredients according to the invention are particularly suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and Spodoptera littoralis in cotton, vegetables, corn, rice and soybean crops. The active ingredients according to the invention are particularly suitable for controlling Mamestra (preferably on vegetables), codling moth (Cydia pomonella) (preferably on apple), Empoasca (preferably on vegetables and vineyards), Leptinotarsa ​​(preferably on potato) and Chilo supressalis (preferably on rice).

[0349] The active ingredients according to the invention are particularly suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and Spodoptera littoralis in cotton, vegetables, corn, rice and soybean crops. The active ingredients according to the invention are particularly suitable for controlling Mamestra (preferably on vegetables), codling moth (Cydia pomonella) (preferably on apple), Empoasca (preferably on vegetables and vineyards), Leptinotarsa ​​(preferably on potato) and Chilo supressalis (preferably on rice).

[0350] In a further aspect, the present invention also relates to plant parasitic nematodes (endoparasitic, semi-endoparasitic and ectoparasitic nematodes), in particular the root-knot nematode Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes Globodera rostochiensis and other Globodera species; wheat cyst nematode Heterodera avenae, soybean cyst nematode Heterodera glycines, sugar beet cyst nematode Heterodera schachtii, clover cyst nematode Heterodera trifolii and other cyst nematodes (Heterodera species); seed gall nematodes, Anguina species; stem and peel nematodes, Aphelenchoides species; sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; pine wood nematode, Bursaphelenchus xylophilus and other Bursaphelenchus species; ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; fire nematodes, Dolichodorus species;Screw nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Spear nematodes, Hoploaimus species; False root-knot nematodes, Nacobbus species; Tylenchidae, Longidorus elongatus elongatus and other Longidorus species; pin nematodes, Pratylenchus species; root-lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; root-lesion nematodes, Radopholus similis and other Radopholus species; false nematodes, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Trichodorus primitivus and other Trichodorus species, Paratrichodorus species;plant-parasitic nematodes such as the claytonid nematode, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; the burrowing nematode, Tylenchulus species; plant-parasitic nematodes such as the giant sting nematode, Xiphinema species; and plant-parasitic nematodes such as Subanguina species, Hypsoperine species, Macroposthonia species, Melinius species, Punctodera species and Quinisulcius species. The present invention may also relate to a method for preventing damage to plants and parts thereof by other plant-parasitic nematode species, such as Pseudomonas spp.;

[0351] The compounds of the present invention may also have activity against mollusks, such as, for example, the family Ampullariidae; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus); Bradybaenidae (Bradybaena furticum); fruticum); Cepaea (C. hortensis, C. nemoralis); Ochlodina; Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum) tum); Discus (D. rotundatus); Euomphalia; Galba (G. trunculata); Helicelia (H. itala, H. obvia); Helicidae (Helicigona albustrum) arbustorum); Helicodiscus; Helix (H. aperta); Limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus); Monoa These include the genera Lymnaea; Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.

[0352] The term "crop plant" should also be understood to include crop plants that have been transformed by the use of recombinant DNA techniques so as to be capable of synthesizing one or more selectively acting toxins, such as those known to be derived from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0353] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, insecticidal proteins from Bacillus thuringiensis or plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A; or bacterial-colonizing nematodes, such as Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus, etc. insecticidal proteins of Azotoxins; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and neurotoxins specific to other insects; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectin, barley lectin or snowdrop lectin; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin and papain inhibitors; ricin, corn-RIP, abrin, rufin, saporin ribosome-inactivating proteins (RIPs) such as erythrin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as blockers of sodium channels or calcium channels, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0354] In the context of the present invention, delta-endotoxins are understood to mean, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, and also specifically hybrid toxins, truncated toxins, and modified toxins. Hybrid toxins are produced recombinantly by combining different domains of these proteins (see, for example, WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the native toxin are replaced. In such amino acid substitutions, preferably a non-naturally occurring protease recognition sequence is inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0355] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 93 / 07278, WO 95 / 34656, EP 0 427 529, EP 451 878 and WO 03 / 052073.

[0356] Methods for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. Deoxyribonucleic acids of the CryI type and their preparation are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0357] The toxins contained in the transgenic plants confer resistance to pests found in a range of insect taxa, but are particularly common in beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera).

[0358] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants include YieldGard® (a corn variety expressing the Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing the Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing the Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing the Cry9C toxin); Herculex I® (a corn variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) for tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing the Cry1Ac toxin); Bollgard I® (a cotton variety expressing the Cry1Ac toxin); Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (a cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0359] Further examples of such transgenic crops are: 1. Bt11 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS (Chemin de l'Hobit 27, F-31 790 St. Sauveur, France). This genetically modified maize is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through the transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also genetically expresses the enzyme PAT to confer tolerance to the herbicide glufosinate ammonium.

[0360] 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS (Chemin de l'Hobit 27, F-31 790 St. Sauveur, France). This genetically modified maize is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the Cry1Ab toxin. Bt176 maize also genetically expresses the enzyme PAT to confer tolerance to the herbicide glufosinate ammonium.

[0361] 3. MIR604 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS (Chemin de l'Hobit 27, F-31 790 St. Sauveur, France). This maize has been made insect-resistant by transgenic expression of a modified Cry3A toxin. The toxin is Cry3A055, modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03 / 018810.

[0362] 4. MON 863 maize, registration number C / DE / 02 / 9, manufactured by Monsanto Europe SA (270-272 Avenue de Tervuren, B-1150 Brussels, Belgium). MON 863 expresses the Cry3Bb1 toxin and confers resistance to certain Coleoptera insects.

[0363] 5. IPC 531 cotton, registration number C / ES / 96 / 02, manufactured by Monsanto Europe SA (270-272 Avenue de Tervuren, B-1150 Brussels, Belgium).

[0364] 6. 1507 Maize, registration number C / NL / 00 / 10, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium. Genetically modified maize for expression of the protein Cry1F for resistance to certain Lepidoptera insects and the protein PAT for resistance to the herbicide glufosinate ammonium.

[0365] 7. NK603 x MON 810 maize, registration number C / GB / 02 / M3 / 03, manufactured by Monsanto Europe SA (270-272 Avenue de Tervuren, B-1150 Brussels, Belgium). This maize consists of a conventionally bred hybrid maize variety by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 maize also genetically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which confers resistance to the herbicide Roundup® (containing glyphosate), and the Cry1Ab toxin, obtained from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain Lepidoptera, including the European corn borer.

[0366] 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).

[0367] The term "crop plant" should also be understood to include crop plants that have been transformed by the use of recombinant DNA technology so as to be able to synthesize antipathogenic substances with selective action, such as, for example, so-called "pathogenicity-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 above-mentioned publications.

[0368] Crops can also be improved to increase resistance to fungal (e.g., Fusarium, anthracnose, or Phytophthora), bacterial (e.g., Pseudomonas), or viral (e.g., potato leaf curl virus, tomato spotted wilt virus, cucumber mosaic virus) pathogens.

[0369] Crops also include those that have a high resistance to nematodes, such as the soybean cyst nematode.

[0370] Crops that are tolerant to abiotic stress include those that have increased tolerance to drought, high salinity, high temperature, low temperature, frost, or light due to, for example, expression of NF-YB or other proteins known in the art.

[0371] Antipathogenic substances that can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers of sodium or calcium channels, e.g., viral KP1, KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; so-called "pathogenesis-related proteins" (PRPs; see, for example, EP 0 392 225); antipathogenic substances produced by microorganisms, such as peptide or heterocyclic antibiotics (see, for example, WO 95 / 33818) or proteins or polypeptide factors involved in plant pathogen defense (the so-called "plant disease resistance genes" described in WO 03 / 000906).

[0372] Further fields of use of the compositions according to the invention are the protection of stored goods and storage rooms and of raw materials (such as wood and textiles), floor coverings and buildings, and in the hygiene sector, in particular the protection of humans, domestic animals and productive livestock from pests of the above-mentioned types.

[0373] The present invention also provides methods 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 a composition of the present invention to the target pest, its habitat, or a surface or substrate by brushing, rolling, spraying, painting, or dipping. By way of example, IRS (indoor residual spray) application of surfaces such as walls, ceilings, or floors is contemplated by the method of the present invention. In another embodiment, it is contemplated to apply such compositions to substrates such as nonwoven or woven materials in the form of (or in a form that can be used to manufacture) netting, clothing, bedding, curtains, and tents.

[0374] In one embodiment, a method for controlling such pests comprises applying a pesticidally effective amount of a composition of the present invention to a target pest, its habitat, or a surface or substrate to provide effective, residual pest control activity to the surface or substrate. Such application may be by brushing, rolling, spraying, painting, or dipping the pesticidal composition of the present invention. For example, IRS application to surfaces such as walls, ceilings, or floors is contemplated by the method of the present invention to provide effective, residual pest control activity to the surface. In another embodiment, the application of such compositions for residual pest control on substrates such as fabric materials in the form of (or in the form that can be used to manufacture) netting, clothing, bedding, curtains, and tents is contemplated.

[0375] The substrates to be treated, including nonwovens, fabrics, or nets, can be made of natural fibers such as cotton, raffia, jute, flax, sisal, hemp, or wool, or synthetic fibers such as polyamide, polyester, polypropylene, or polyacrylonitrile. Polyesters are particularly suitable. Methods for treating textiles are known, for example, from WO 2008 / 151984, WO 2003 / 034823, U.S. Pat. No. 5,631,072, WO 2005 / 64072, WO 2006 / 128870, EP 1 724 392, WO 2005 113 886, or WO 2007 / 090739.

[0376] A further field of use for the compositions according to the invention is that of trunk injection / trunk treatment of all ornamental trees and all kinds of fruit and nut-bearing trees.

[0377] In the field of trunk injection / trunk treatment, the compounds according to the invention are particularly suitable against wood-boring insects of the above-mentioned orders Lepidoptera and Coleoptera, in particular the woodborers listed in Tables A and B below.

[0378] [Table 3]

[0379] [Table 4] JPEG2024539980000034.jpg206156

[0380] The present invention may be used to control any insect pest that may be present in turfgrass, including, for example, beetles, caterpillars, fire ants, ground pearls, millipedes, pill bugs, mites, mole crickets, scale insects, mealybugs, mites, boxworms, southern chinch bugs, and grubs. The present invention may also be used to control insect pests in various stages of their life cycle, including eggs, larvae, nymphs, and adults.

[0381] In particular, the present invention relates to the treatment of grubs (Cyclocephala spp. (e.g., masked chafer, C. lurida), Rhizotrogus spp. (e.g., European chafer, R. majalis), Cotinus spp. (e.g., blue swallowtail, C. nitida), Popillia spp. (e.g., Japanese beetle, P. japonica), Phyllophaga spp. (e.g., May / June beetle), Ataenius spp., and the like). spp. (e.g., Black turfgrass ataenius, A. spretulus), Maladera spp. (e.g., red-veined scarab beetle, M. castanea) and Tomarus spp.), cotton bollworms (Margarodes spp.), mole crickets (tawny, southern and brachypterous; Scapteriscus spp., Gryllotalpa africana) and leatherjackets (European crane fly, Tipula The compounds may be used to control insect pests that feed on the roots of turfgrass, including Pseudomonas spp.

[0382] The present invention may also be used to control straw-dwelling insect pests of turfgrass, including cutworms (such as Spodoptera frugiperda and the common armyworm (Pseudaletia unipuncta)), cutworms, weevils (such as Sphenophorus spp., S. venatus verstitus, and S. parvulus) and sod webworms (such as Crambus spp. and the tropical sod webworm, Herpetogramma phaeopteralis).

[0383] The present invention may also be used to control insect pests that live on the ground and feed on turfgrass leaves, including the lesser stink bug (such as the southern kinkbag, Blissus insularis), bermudagrass mite (Eriophyes cynodoniensis), rhodesgrass mealybug (Antonina graminis), two-lined spittlebug (Propsapia bicincta), leafhoppers, cutworms (Noctuidae), and greengrass aphids.

[0384] The present invention may also be used to control other pests of turfgrass, such as the red fire ant (Solenopsis invicta), which creates ant mounds in turfgrass.

[0385] In the hygiene field, the compositions according to the invention are effective against ectoparasites such as hard ticks, soft ticks, scabies mites, chiggers, flies (stable flies and licking flies), parasitic fly larvae, lice, pubic lice, biting lice and fleas.

[0386] Examples of such parasites are: Among the Anoplurida, the genera Haematopinus, Linognathus, Pediculus, Phtirus, and Solenopotes are included.

[0387] From the order Mallophagida, the genera Trimenopon, Menopon, Trinoton, Bovicola, Werneckiella, Lepikentron, Damalina, Trichodectes and Felicola.

[0388] Among the order Diptera and its suborders Nematocerina and Brachycerina, for example, the genera Aedes, Anopheles, Culex, Simulium, Eusimulium, Phlebotomus, Lutzomyia, Culicoides, Chrysops, Hybomitra, Atylotus, Tabanus, Haematopota, spp.), Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp.), sheep flies (Oestrus spp.), cow flies (Hypoderma spp.), bot flies (Gasterophilus spp.), hood flies (Hippobosca spp.), deer flies (Lipoptena spp.) and sheep hood flies (Melophagus spp.).

[0389] Among the Siphonapterida, for example, the human flea genus (Pulex spp.), the dog flea genus (Ctenocephalides spp.), the mouse flea genus (Xenopsylla spp.), and the long flea genus (Ceratophyllus spp.).

[0390] From the order Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., and Panstrongylus spp.

[0391] From the order Blattaria, for example, the Asian cockroach (Blatta orientalis), the American cockroach (Periplaneta americana), the German cockroach (Blattela germanica) and the genus Supella.

[0392] Among the subclass Acaria (Acarida) and the suborder Metastigmata and Mesostigmata, for example, the genera Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp. spp.), Pneumonyssus spp., Sternostoma spp. and Varroa spp.

[0393] From the orders Actinedida (Prostigmata) and Acaridida (Astigmata), for example, the genera Acarapis, Cheyletiella, Ornithocheyletia, Myobia, Psorergates, Demodex, Trombicula, Listrophorus, Acarus, Tyrophagus, Caloglyphus, Hypodectes spp.), Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0394] The compositions according to the invention are also suitable for protecting against insect infestation in materials such as wood, textiles, plastics, adhesives, glues, paints, paper and cardboard, leather, floor coverings and building materials.

[0395] The compositions according to the invention can be used, for example, against the following pests: European house borer (Hylotrupes bajulus), Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, pine wood beetle (Ernobius mollis), longhorn beetle (Priobium carpini), flat-headed beetle (Lyctus brunneus), African flat-headed beetle (Lyctus africanus), American flat-headed beetle (Lyctus planicollis), oak flat-headed beetle (Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec.and Dinoderus minutus, as well as hymenopteran insects such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, and Urocerus augur, as well as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, and other insects of the genus Kalotermes. Termites such as Mastotermes darwiniensis, Zootermopsis nevadensis, and Coptotermes formosanus, as well as wood mites such as Lepisma saccharina.

[0396] Although the compounds of the present invention can be used as pesticides in their native form, they are generally formulated into compositions using formulation aids such as carriers, solvents, and surfactants in various ways. The formulations can be in various physical forms, such as dustable powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil-based flowables, aqueous dispersions, oil-based dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (containing water or a water-miscible organic solvent as a carrier), impregnated polymer films, or other forms known from, for example, the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can be used directly or diluted before use. Dilution can be carried out, for example, with water, liquid fertilizers, trace elements, biological materials, oils, or solvents.

[0397] The formulations can be prepared by mixing the active ingredient with formulation aids to obtain a composition in the form of, for example, finely divided solids, granules, solutions, dispersions, or emulsions. The active ingredient can also be formulated with other adjuvants, such as finely divided solids, mineral oil, vegetable or animal oil, modified vegetable or animal oil, organic solvent, water, surfactant, or combinations thereof.

[0398] The active ingredient can also be contained in extremely fine microcapsules. Microcapsules contain the active ingredient in a porous carrier, allowing the active ingredient to be released into the environment in controlled amounts (e.g., sustained release). Microcapsules typically have diameters of 0.1 to 500 microns. They contain the active ingredient in an amount of about 25 to 95% by weight of the capsule. The active ingredient can be in the form of a bulk solid, fine particles in a solid or liquid dispersion, or a suitable solution. The encapsulating membrane can comprise, 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, extremely fine microcapsules can be formed containing the active ingredient in the form of fine particles in a base solid matrix, but the microcapsules themselves are not encapsulated.

[0399] The formulation auxiliaries suitable for preparing the compositions according to the invention are known per se. Examples of liquid carriers include 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 esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietic acid, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, 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, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate Examples of suitable solvents include ethanol, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, 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 high molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, and N-methyl-2-pyrrolidone.

[0400] Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, Kiesslager, limestone, calcium carbonate, bentonite, calcium montmorillonite, cotton hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin, and similar materials.

[0401] Many surface-active substances can be used advantageously in both solid and liquid formulations, especially in formulations that can be diluted with a carrier before use. The surface-active substances can be anionic, cationic, nonionic, or polymeric, and they can be used as emulsifying agents, wetting agents, or suspending agents, or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide adducts such as nonylphenol ethoxylate; alcohol / alkylene oxide adducts such as tridecyl alcohol ethoxylate; soaps such as sodium stearate; salts of alkylnaphthalenesulfonates such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryltrimethylammonium 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 di-alkyl phosphate esters; and further substances described, for example, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey (1981).

[0402] Additional adjuvants that may be used in the pest control formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, antifoaming agents, complexing agents, neutralizing or pH adjusting and buffering agents, corrosion inhibitors, fragrances, wetting agents, uptake enhancers, trace elements, plasticizers, glidants, lubricants, dispersants, thickeners, antifreeze agents, fungicides and liquid and solid fertilizers.

[0403] The compositions of the present invention may contain additives including vegetable or animal oils, mineral oils, alkyl esters of such oils, or mixtures of such oils and oil derivatives. The amount of oil additive in the compositions of the present invention is generally 0.01 to 10% based on the mixture to be applied. For example, the oil additive can be added to the spray tank at the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oils or vegetable oils such as rapeseed oil, olive oil, or sunflower oil, emulsified vegetable oils, alkyl esters of vegetable oils such as methyl derivatives, or animal oils such as fish oil or beef tallow. Preferred oil additives are C8 to C 22 Alkyl esters of fatty acids, especially C 12 ~C 18 Methyl derivatives of fatty acids, including, for example, the methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are listed in the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.

[0404] The compositions of the present invention generally comprise 0.1 to 99% by weight, especially 0.1 to 95% by weight, of the compounds of the present invention and 1 to 99.9% by weight of formulation aids, which preferably include 0 to 25% by weight of surfactants. Although commercial products may preferably be formulated as concentrates, end users will typically utilize diluted formulations.

[0405] The application rates vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pests to be controlled, the prevailing weather conditions and other factors which depend on the method, time of application and the target crop. As a general guideline, the compounds may be applied in amounts of 1 to 2000 l / ha, especially 10 to 1000 l / ha.

[0406] A preferred formulation may have the following composition (by weight): Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surface active agent: 1 to 30%, preferably 5 to 20% Liquid carrier: 1 to 80%, preferably 1 to 35%

[0407] Powder: Active ingredient: 0.1 to 10%, preferably 0.1 to 5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

[0408] Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surface active agent: 1 to 40%, preferably 2 to 30%

[0409] Wettable powder: Active ingredient: 0.5 to 90%, preferably 1 to 80% Surface active agent: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 95%, preferably 15 to 90%

[0410] Granules: Active ingredient: 0.1 to 30%, preferably 0.1 to 15% Solid carrier: 99.5 to 70%, preferably 97 to 85%

[0411] The following examples further illustrate, but do not limit, the present invention.

[0412] [Table 5]

[0413] The complex is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a wettable powder that can be diluted with water to obtain a suspension of the desired concentration.

[0414] [Table 6]

[0415] The complex is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be used directly as a seed treatment.

[0416] [Table 7]

[0417] Emulsions of any required dilution that can be used for plant protection are available from this concentrate by dilution with water.

[0418] [Table 8]

[0419] Ready-to-use dusts are obtained by mixing the complex with a carrier and grinding the mixture in a suitable mill. Such powders can also be used as dry seed dressings.

[0420] [Table 9]

[0421] The compound is mixed and ground with the adjuvant, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0422] [Table 10]

[0423] In a mixer, the finely ground composite is applied uniformly to kaolin moistened with polyethylene glycol, resulting in coated granules that do not generate dust.

[0424] [Table 11]

[0425] The finely divided composite is thoroughly mixed with adjuvants to give a suspension concentrate which can be diluted with water to give a suspension of any desired dilution, and can be used to treat and protect living plants and plant propagation material against microbial infestation by spraying, pouring or dipping.

[0426] [Table 12]

[0427] The finely ground composite is thoroughly mixed with adjuvants to give a suspension concentrate which can be diluted with water to give a suspension of any desired dilution, and such dilutions can be used to treat and protect living plants and plant propagation material against microbial infestation by spraying, pouring or dipping.

[0428] slow-release capsule suspension 28 parts of the composite are mixed with 2 parts aromatic solvent and 7 parts toluene diisocyanate / polymethylene-polyphenylisocyanate (8:1) mixture. This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts defoamer, and 51.6 parts water until the desired particle size is achieved. A mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water is added to this emulsion. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by adding 0.25 parts thickener and 3 parts dispersant. The capsule suspension formulation contains 28% active ingredient. The diameter of the medium-sized capsules is 8 to 15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for this purpose.

[0429] 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 (EO), emulsions, oil-in-water (EW), microemulsions (ME), oil dispersions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG) or any technically preferred formulation in combination with agriculturally acceptable adjuvants. [Example]

[0430] Preparation example: "Mp" means melting point (°C). The free radical represents a methyl group. 1 H NMR measurements were recorded on a Brucker 400 MHz spectrometer and chemical shifts are given in ppm relative to a TMS standard. Spectra were run in deuterated solvents as specified. Compounds were characterized using one of the following LCMS methods. The unique LCMS values ​​obtained for each compound consist of the retention time ("Rt", reported in minutes) and the observed molecular ion (M+H). + or (M+H) - It was.

[0431] LCMS and GCMS methods: Method 1: Spectra were recorded on a Waters Corporation mass spectrometer (SQD, SQDII, or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative ions), capillary: 0.8-3.00 kV, cone: 5-30 V, source temperature: 120-150 °C, desolvation temperature: 350-600 °C, cone gas flow: 50-150 l / h, desolvation gas flow: 650-1000 l / h, mass range: 110-950 Da, and a Waters Corporation Acquity UPLC: binary pump, heated column compartment, diode-array detector, and ELSD. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, Temperature: 60 °C, DAD wavelength range (nm): 210–400, Run time: 1.5 min; Solvents: A = water + 5% MeOH + 0.05% HC(O)OH, B = acetonitrile + 0.05% HC(O)OH; Flow (ml / min): 0.85, Gradient: isocratic at 10% B for 0.2 min, then 10–100% B for 1.0 min, isocratic at 100% B for 0.2 min, 100–10% B for 0.05 min, isocratic at 10% B for 0.05 min.

[0432] Method 2: Spectra were recorded on a Waters Corporation mass spectrometer (SQD, SQDII, or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative ions), capillary: 0.8-3.00 kV, cone: 5-30 V, source temperature: 120-150 °C, desolvation temperature: 350-600 °C, cone gas flow: 50-150 l / h, desolvation gas flow: 650-1000 l / h, mass range: 110-950 Da, and a Waters Corporation Acquity UPLC: binary pump, heated column compartment, diode-array detector, and ELSD. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, Temperature: 60 °C, DAD wavelength range (nm): 210–400, Run time: 3.0 min; Solvents: A = water + 5% MeOH + 0.05% HC(O)OH, B = acetonitrile + 0.05% HC(O)OH; Flow (ml / min): 0.85, Gradient: isocratic at 10% B for 0.2 min, then 10–100% B in 2.5 min, isocratic at 100% B for 0.3 min.

[0433] Method 3: Spectra were recorded on a Waters mass spectrometer (SQD2 or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: switched anode and cathode), capillary voltage: 0.8–3.00 kV, cone range: 25°C, source temperature: 120–150°C, desolvation temperature: 500–600°C, cone gas flow: 50 L / h, desolvation gas flow: 1000 L / h, mass range: 110–850 Da) and a Waters Acquity UPLC: Quaternary solvent manager, heated column compartment, and diode-array detector. Column: Acquity UPLC HSS T3 C18, 1.8 μm, 30 × 2.1 mm; Temperature: 40 °C; DAD wavelength range (nm): 200–400; Solvent gradient: A = water + 5% acetonitrile + 0.1% HC(O)OH, B = acetonitrile + 0.05% HC(O)OH; Gradient: 0 min 10% B; 0.–0.2 min 10–50% B; 0.2–0.6 min 50–100% B; 0.6–1.3 min 100% B; 1.3–1.4 min 100–10% B; 1.4–1.6 min 10% B; Flow (mL / min) 0.6.

[0434] Method 4: Spectra were recorded on an Agilent Technologies mass spectrometer (MSD-IQ mass spectrometer) equipped with an electrospray source (polarity: positive or negative ion, MS2 Scan, capillary: 3.5 kV, fragmentor: 110 V, desolvation temperature: 325 °C, gas flow: 13 L / min, nebulizer gas: 55 psi, mass range: 110–850 Da) and an Agilent 1290 Series HPLC: quaternary pump, heated column compartment, and diode-array detector. Column: AGILENT POROSHELL 120 EC-C18, 1.9 μm, 50 × 2.1 mm; Temperature: 40 °C; DAD wavelength range (nm): 190–400; Solvent gradient: A = water + 5% acetonitrile + 0.1% HC(O)OH, B = acetonitrile + 0.1% HC(O)OH; Gradient: 0–0.5 min 10% B, 90% A; 1.2–1.5 min 95% B, 0.5% A; 1.8–2.5 min 10% B, 90% A; Flow (mL / min): 0.8.

[0435] Method 5: Spectra were recorded on a Waters Corporation ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive or negative, capillary: 3.0 kV, cone: 30 V, extractor: 3.00 V, source temperature: 150 °C, desolvation temperature: 400 °C, cone gas flow: 60 L / hr, desolvation gas flow: 700 L / hr, mass range: 140-800 Da) and a Waters Corporation ACQUITY UPLC equipped with a solvent degasser, binary pump, heated column compartment, and diode-array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210–400; Solvent gradient: A = water / methanol 9:1 + 0.1% formic acid, B = acetonitrile + 0.1% formic acid; Gradient: 0–100% B in 2.5 min; Flow (ml / min): 0.75.

[0436] Example P1: Preparation of 3-(3-ethylsulfanyl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (compound P1) [ka] Step 1: Preparation of (E)-3-(dimethylamino)-1-[2-hydroxy-4-(trifluoromethyl)phenyl]prop-2-en-1-one (Intermediate I1) [ka] A mixture of 1-(2-hydroxy-4-trifluoromethyl)phenyl)ethanone (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, then 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] + .

[0437] Step 2: Preparation of 3-iodo-7-(trifluoromethyl)chromen-4-one (Intermediate I2) [ka] 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., iodine (7.00 g, 27.6 mmol, 1.2 equiv.) was added. The reaction mixture was stirred at room temperature for 17 hours. The mixture was diluted with aqueous sodium thiosulfate and stirred for 15 minutes. The precipitate formed was filtered and then dissolved in ethyl acetate. The organic phase was washed twice with brine, dried over magnesium sulfate, and concentrated in vacuo using an 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] + .

[0438] Step 3: Preparation of [4-oxo-7-(trifluoromethyl)chromen-3-yl]boronic acid (intermediate I3) [ka] 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, isopropylmagnesium chloride lithium chloride complex (1.3 M in THF) (0.95 mL, 1.23 mmol, 1.4 equiv.) was added dropwise. The reaction mixture was stirred at -78 °C for 15 minutes, after which trimethyl borate (0.25 mL, 2.21 mmol, 2.5 equiv.) was added. The reaction mixture was then warmed to room temperature and stirred for 2 hours. The mixture was diluted with aqueous ammonium chloride, the product was extracted twice with ethyl acetate, and 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] + .

[0439] Step 4: Preparation of 2-bromo-3-ethylsulfanyl-pyridine (Intermediate I4) [ka] To a solution of 2-bromo-3-fluoro-pyridine (CAS: 40273-45-8) (24.9 g, 141 mmol) in N,N-dimethyl-formamide (80 mL) cooled at -50 °C was added sodiothioethane (13.2 g, 141 mmol, 1 equiv.). The reaction mixture was cooled to -60 °C, stirred at this temperature for 20 min, and then warmed to room temperature. The reaction mixture was diluted with water and ethyl acetate. The aqueous phase was extracted with ethyl acetate (3 times). The combined organic phases were washed twice with water, then with brine, dried over magnesium sulfate, and concentrated in vacuo using an isolute. The crude material was purified by flash chromatography on silica gel (ethyl acetate in cyclohexane) to give the desired product as a colorless oil. LCMS (Method 1): Rt = 0.94 min, m / z 218 / 220 [M+H] + .

[0440] Step 5: Preparation of 3-(3-ethylsulfanyl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (compound P1) [ka] To a solution of 2-bromo-3-ethylsulfanyl-pyridine (0.025 g, 0.116 mmol) and [4-oxo-7-(trifluoromethyl)chromen-3-yl]boronic acid (0.03 g, 0.116 mmol, 1 equiv.) in dioxane (0.46 mL) degassed with argon, 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex was added along with dichloromethane (0.010 g, 0.0116 mmol, 0.1 equiv.), water (0.17 mL), and potassium carbonate (0.048 g, 0.348 mmol, 3 equiv.). The reaction mixture was stirred at 60 °C for 70 min under an argon atmosphere. The mixture was cooled to room temperature, diluted with aqueous sodium bicarbonate, and the product was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (ethyl acetate in cyclohexane) to give the desired product. LCMS (Method 1): Rt=1.03 min, m / z 352 [M+H] + .

[0441] Example P2: Preparation of 3-(3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (compound P2) [ka] To a solution of 3-(3-ethylsulfanyl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (0.048 g, 0.137 mmol) in ethyl acetate (0.72 mL) at 0° C., 3-chlorobenzoic acid (0.064 g, 0.288 mmol, 2.1 equiv.) was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with aqueous sodium bisulfite, and the product was extracted with ethyl acetate. The organic phase was washed with water, then with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by preparative HPLC (acetonitrile in water + formic acid) to give the desired product as a solid. LCMS (Method 1): Rt = 0.91 min, m / z 384 [M+H] + .1 H NMR(400MHz,CDCl3)δ ppm 1.34(t,3H),3.40(q,2H),7.62(dd,1H),7.71(dd,1H),7.85(s,1H),8.16(s,1H),8.42(m,2H),8.94(dd,1H).

[0442] Example P3: Preparation of 1-[5-ethylsulfanyl-6-[4-oxo-7-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropane-carbonitrile (compound P3) [ka] Step 1: Preparation of 1-(6-bromo-5-ethylsulfanyl-3-pyridyl)cyclopropanecarbonitrile (Intermediate I5) [ka] To a solution of 1-(6-amino-5-ethylsulfanyl-3-pyridyl)cyclopropanecarbonitrile (prepared as described in WO 2020 / 174094) (6.95 g, 31.7 mmol) in ethylene dibromide (69.5 mL) was added copper(II) bromide (10.7 g, 47.5 mmol, 1.5 equiv.). The reaction mixture was stirred at room temperature for 10 minutes, after which isoamyl nitrite (6.52 mL, 47.5 mmol, 1.5 equiv.) was added dropwise. The mixture was further stirred at room temperature for 4.5 hours. The reaction mixture was diluted with aqueous sodium bicarbonate and ethyl acetate and then filtered through Celite. The aqueous phase was extracted twice with ethyl acetate. The combined organic phase was washed with water, then with aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under reduced pressure using isolute. The crude material was purified by flash chromatography on silica gel (ethyl acetate in cyclohexane) to give the desired product as a yellow solid. LCMS (Method 1): Rt=0.99 min, m / z 283 / 285 [M+H] + . 1H NMR(400MHz,CDCl3)δ ppm 1.44(t,3H),1.47(m,2H),1.83(m,2H),3.01(q,2H),7.45(d,1H),7.94(d,1H).

[0443] Step 2: Preparation of 1-[5-ethylsulfanyl-6-[4-oxo-7-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropane-carbonitrile (compound P3) [ka] To a solution of 1-(6-bromo-5-ethylsulfanyl-3-pyridyl)cyclopropanecarbonitrile (0.030 g, 0.106 mmol) and [4-oxo-7-(trifluoromethyl)chromen-3-yl]boronic acid (0.027 g, 0.106 mmol, 1 equiv.) in acetonitrile (0.82 mL) degassed with argon, 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex was added along with dichloromethane (0.009 g, 0.011 mmol, 0.1 equiv.), water (0.32 mL), and potassium carbonate (0.037 g, 0.265 mmol, 2.5 equiv.). The reaction mixture was stirred at 60 °C for 45 min under an argon atmosphere. The mixture was cooled to room temperature, diluted with aqueous sodium bicarbonate, and the product was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (ethyl acetate in cyclohexane) to give the desired product as a solid. LCMS (Method 1): Rt = 1.07 min, m / z 417 [M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 1.29(t,3H),1.54(m,2H),1.87(m,2H),2.95(q,2H),7.69(d,1H),7.72(d,1H),7.83(s,1H),8.13(s,1H),8.34(d,1H),8.44(d,1H).

[0444] Example P4: Preparation of 1-[5-ethylsulfonyl-6-[4-oxo-7-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropane-carbonitrile (compound P4) [ka] Step 1: Preparation of 1-(6-bromo-5-ethylsulfonyl-3-pyridyl)cyclopropanecarbonitrile (Intermediate I6) [ka] To a solution of 1-(6-bromo-5-ethylsulfanyl-3-pyridyl)cyclopropanecarbonitrile (4.19 g, 14.8 mmol) in ethyl acetate (59 mL) at 0° C., 3-chlorobenzoic acid (7.83 g, 34 mmol, 2.3 equiv.) was added portionwise, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched by dropwise addition of aqueous sodium bisulfite, stirred for 10 minutes, then diluted with aqueous sodium bicarbonate, and the product was extracted with ethyl acetate. The organic phase was washed with aqueous sodium hydroxide, then aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was used directly without any purification. LCMS (Method 1): Rt=0.77 min, m / z 315 / 317 [M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 1.34(t,3H),1.55(m,2H),1.94(m,2H),3.56(q,2H),8.17(d,1H),8.67(d,1H).

[0445] Step 2: Preparation of 1-[5-ethylsulfonyl-6-[4-oxo-7-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropane-carbonitrile (compound P4) [ka] To an argon-degassed solution of 1-(6-bromo-5-ethylsulfonyl-3-pyridyl)cyclopropanecarbonitrile (0.696 g, 2.7 mmol) and [4-oxo-7-(trifluoromethyl)chromen-3-yl]boronic acid (0.858 g, 2.7 mmol, 1 equiv.) in acetonitrile (14 mL) was added 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex along with dichloromethane (0.231 g, 0.27 mmol, 0.1 equiv.), water (5.4 mL), and potassium carbonate (0.858 g, 6.21 mmol, 2.3 equiv.) at 0 °C. The mixture was stirred at 60 °C for 20 min. The reaction mixture was cooled to room temperature, diluted with water, and the product was extracted twice with ethyl acetate. The combined organic phases were washed with aqueous sodium hydroxide and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo using an isolute. The crude material was purified by flash chromatography on silica gel (ethyl acetate in cyclohexane) to give the desired product as a solid. LCMS (Method 1): Rt = 0.98 min, m / z 449 [M+H] + .

[0446] Example P5: Preparation of 3-(5-bromo-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)-chromen-4-one (compound P9) [ka] Step 1: 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-1-[2-hydroxy-4-(trifluoromethyl)phenyl]ethanone (Intermediate I7) [ka] To a solution of 2-hydroxy-4-(trifluoromethyl)phenyl-ethanone (3.00 g, 14.70 mmol) and 2,5-dibromo-3-ethylsulfonyl-pyridine (4.835 g, 14.70 mmol) in DMSO (21 mL) was added potassium carbonate (2.641 g, 19.104 mmol, 1.30 equiv.). The mixture was stirred at room temperature for 1 day. Additional potassium carbonate (2.0 g) was then added, and the mixture was stirred at room temperature for another day. Water was then added, and the mixture was extracted twice with ethyl acetate. The combined organic phases were washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by chromatography (cyclohexane-ethyl acetate-1% AcOH) to give 3.18 g of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-1-[2-hydroxy-4-(trifluoromethyl)phenyl]-ethanone. LCMS (method 1): Rt=1.10 min, m / z452 / 454[M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 1.34(t,3H),3.24(q,2H),5.12(s,2H),7.24(d,1H),7.31(s,1H),8.02(d,1H),8.48(d,1H),8.87(d,1H),11.78(s,1H).

[0447] Step 2: 3-(5-Bromo-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)-chromen-4-one (compound P9) [ka] A mixture of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-1-[2-hydroxy-4-(trifluoromethyl)phenyl]ethanone (2.48 g, 5.48 mmol) and N,N-dimethylformamide dimethyl acetal (0.949 mL, 7.13 mmol, 1.30 equiv.) in methanol (19.8 mL) was stirred under reflux for 2.5 h. Water was then added, and the mixture was extracted twice with ethyl acetate. The combined organic phases were washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. Chromatography (cyclohexane-ethyl acetate) afforded a mixture of the desired product and starting material. The mixture was dissolved in methanol (20 mL), and N,N-dimethylformamide dimethyl acetal (0.5 mL) was added. The mixture was stirred at reflux for 16 h. LC / MS showed complete conversion with no trace of starting material. Water was added, and the mixture was extracted twice with ethyl acetate. The combined organic phases were washed with water and brine, dried over magnesium sulfate, filtered and concentrated to give 1.66 g of 3-(5-bromo-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)-chromen-4-one. LCMS (Method 1): Rt=1.04 min, m / z 462 / 464 [M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 1.38(t,3H),3.43(q,2H),7.72(d,1H),7.88(s,1H),8.18(s,1H),8.41(d,1H),8.54(d,1H),8.98(d,1H).

[0448] Example P6: Preparation of 3-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P16) [ka] To a solution of 3-(5-bromo-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (105 mg, 0.227 mmol) in toluene (20 mL) and water (4 mL) was added sodium carbonate (61 mg, 0.568 mmol, 2.5 equiv.) and (4-fluorophenyl)boronic acid (111 mg, 0.7951 mmol, 3.5 equiv.). The reaction mixture was stirred at room temperature under a nitrogen atmosphere, and then tetrakis-(triphenylphosphine)-palladium(0) (27 mg, 0.0227 mmol, 0.1 equiv.) was added, and the reaction mixture was stirred at 90° C. for 12 hours. After the reaction was complete, the reaction mass was cooled to room temperature, and water (20 mL) was added. The mixture was extracted with ethyl acetate (3 times). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography using 30% ethyl acetate in cyclohexane to give 65 mg of 3-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridyl]-7-(trifluoromethyl)chromen-4-one. LCMS (Method 3): Rt=1.07 min, m / z 478 [M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 1.37(t,3H),3.43(d,2H),7.15-7.28(m,2H),7.60-7.69(m,2H),7.73(d,1H),7.87(s,1H),8.21(s,1H),8.42(d,1H),8.54(d,1H),9.10(broad) s,1H).

[0449] [Table 13] JPEG2024539980000061.jpg250159 JPEG2024539980000062.jpg249160 JPEG2024539980000063.jpg249152 JPEG2024539980000064.jpg249155 JPEG2024539980000065.jpg107166

[0450] The activity of the compositions according to the invention can be considerably broadened and adapted to epidemic situations by adding other insecticidally, acaricidally and / or fungicidal active ingredients. Mixtures of compounds of formula I with other insecticidally, acaricidally and / or fungicidal active ingredients can also have further unexpected advantages, which can be described in a broader sense as synergistic activity, such as better plant resistance, lower herbicidal activity, the ability to control insects at different stages of development, or better behavior during their preparation, for example during grinding or mixing, during their storage, or during their use.

[0451] Suitable additives for the active ingredients here are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, urea, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylurea, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

[0452] The following mixtures of compounds of formula I with active ingredients are preferred (the abbreviation "TX" means "one compound selected from the group consisting of the compounds described in Tables A-1 to A-36, Tables B-1 to B-36, Tables C-1 to C-36, and Tables D-1 to D-36, and Table P of the present invention"): An adjuvant selected from the group of substances consisting of petroleum (alternative name) (628) + TX; Abamectin +TX, Acequinocyl +TX, Acetamiprid +TX, Acetoprole +TX, Acrinathrin +TX, Acinonapyr +TX, Afidopiropen +TX, Afoxolaner +TX, Alanycarb +TX, Allethrin +TX, α-Cypermethrin +TX, Alphamethrin +TX, Amidoflumet +TX, Aminocarb +TX, Azocyclotine +TX, Bensultap +TX, Benzoximate +TX, Benzpyrimoxane + TX, beta-cyfluthrin + TX, beta-cypermethrin + TX, bifenazate + TX, bifenthrin + TX, binapacryl + TX, bioallethrin + TX, S bioallethrin + TX, bioresmethrin + TX, bistrifluron + TX, brofuranilide + TX, brofluthrinate + TX, bromophos-ethyl + TX, buprofezin + TX, butocarboxim + TX, cadusafos + TX, carbaryl + TX, carbosulfan + TX, Kartap+TX, CAS number: 1632218-00-8+TX, CAS number: 1808115-49-2+TX, CAS number: 2032403-97-5+ TX, CAS number:2044701-44-0+TX, CAS number:2128706-05-6+TX, CAS number:2095470-94-1+TX, CAS number:2 377084-09-6+TX, CAS number: 1445683-71-5+TX, CAS number: 2408220-94-8+TX, CAS number: 2408220-91- 5+TX, CAS number: 1365070-72-9+TX, CAS number: 2171099-09-3+TX, CAS number: 2396747-83-2+TX, CAS number :2133042-31-4+TX, CAS number:2133042-44-9+TX, CAS number:1445684-82-1+TX, CAS number:1445684- 82-1+TX, CAS number:1922957-45-6+TX, CAS number:1922957-46-7+TX, CAS number:1922957-47-8+TX, CA S number: 1922957-48-9+TX, CAS number: 2415706-16-8+TX, CAS number: 1594624-87-9+TX, CAS number: 159463 7-65-6+TX, CAS number: 1594626-19-3+TX, CAS number: 1990457-52-7+TX, CAS number: 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.: RNA (Colorado potato beetle (Leptinotarsa decemLineata)-specific recombinant double-stranded interference (GS2) + TX, CAS No.: 2719848-60-7 + TX, CAS No.: 1956329-03-5 + TX, chlorantraniliprole + TX, chlordane + TX, chlorfenapyr + TX, chlorprallethrin + TX, chromafenozide + TX, clenpirin + TX, cloetocarb + TX, clothianidin + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, cyanofenphos +TX, cyantraniliprole +TX, cyclaniliprole +TX, cyclobutrifluram +TX, cycloprothrin +TX, cycloxapride +TX, cyenopyrafen +TX, cetopyrafen (or ethopyrafen) +TX, cyflumetofen +TX, cyfluthrin +TX, cyhalodiamide +TX, cyhalothrin +TX, cypermethrin +TX, cyphenothrin +TX, cyprofanilide +TX, cyromazine +TX, deltamethrin +TX, diafenthin Uron + TX, Dialifos + TX, Dibrom + TX, Dichloromezothiaz + TX, Diflobidazin + TX, Diflubenzuron + TX, Dinpropylidaz + TX, Dinactin + TX, Dinocap + TX, Dinotefuran + TX, Dioxabenzophos + TX, Emamectin (or Emamectin benzoate) + TX, Empenthrin + TX, Epsilon-Monfluorothrin + TX, Epsilon-Metofluthrin + TX, Esfenvalerate + TX, Ethion + TX, Ethion Tiprole +TX, Etofenprox +TX, Etoxazole +TX, Famflur +TX, Fenazaquin +TX, Fenfluthrin +TX, Fenmezodithiaz +TX, Fenitrothion +TX, Fenobucarb +TX, Fenothiocarb +TX, Fenoxycarb +TX, Fenpropathrin +TX, Fenpyroximate +TX, Fensulfothion +TX, Fenthion +TX, Fentin acetate +TX, Fenvalerate +TX, Fipronil +TX,Flometquine +TX, Flonicamid +TX, Fluacrypyrim +TX, Fluazaindolizine +TX, Fluazuron +TX, Flubendiamide +TX, Flubenzoimine +TX, Fluchlordiniliprole +TX, Flucythrinate +TX, Flucycloxuron +TX, Flucythrinate +TX, Fluensulfone +TX, Flufenerim +TX, Flufenprox +TX, Flufiprole +TX, Fluhexafon +TX, Flumethrin +TX, Fluopyram +TX, Flupentiofenox +TX, Flupyradifurone +TX, Flupirimine +TX X, fluralaner + TX, fluvalinate + TX, fluxamethamide + TX, fosthiazate + TX, gamma-cyhalothrin + TX, guadipyr + TX, halofenozide + TX, halfenprox + TX, heptafluthrin + TX, hexythiazox + TX, hydramethylnon + TX, imicyafos + TX, imidacloprid + TX, imiprothrin + TX, indazapiroxameth + TX, indoxacarb + TX, iodomethane + TX, iprodione + TX, isocycloceram + TX, isothioate + TX, ivermectin + TX, kappa-bifu Fentrin + TX, kappa-tefluthrin + TX, lambda-cyhalothrin + TX, lepimectin + TX, lotilaner + TX, lufenuron + TX, metaflumizone + TX, metaldehyde + TX, metam + TX, methomyl + TX, methoxyfenozide + TX, metofluthrin + TX, metolcarb + TX, mexacarbate + TX, milbemectin + TX, momfluorotrin + TX, niclosamide + TX, nicofluprole + TX, nitenpyram + TX, nithiazine + TX, omethoate + TX, oxamyl + TX, oxazosulfil + TX, parathion Onethyl + TX, Permethrin + TX, Fenothrin + TX, Phosphocarb + TX, Piperonyl butoxide + TX, Pirimicarb + TX, Pirimiphos-ethyl + TX, Pirimiphos-methyl + TX, Polyhedrosis virus + TX, Prallethrin + TX, Profenofos + TX, Profluthrin + TX, Propargite + TX, Propetamphos + TX, Propoxur + TX, Prothiofos + TX, Protrifenbut + TX, Piflubumid + TX, Pymetrozine + TX, Pyraclofos + TX, Pyrafluprole + TX, Pyridaben + TX, Pyridalyl + TX,Pyrifluquinazone +TX, pyrimidifen +TX, pyriminostrobin +TX, pyriprole +TX, pyriproxyfen +TX, resmethrin +TX, sarolaner +TX, selamectin +TX, silafluofen +TX, spinetoram +TX, spinosad +TX, spirobudifen +TX, spirodiclofen +TX, spiromesifen +TX, spiropydione +TX, Spirotetramat +TX, Spidoxamat +TX, Sulfoxaflor +TX, Tebufenozide +TX, Tebufenpyrad +TX, Tebupirimiphos +TX, Tefluthrin +TX, Temephos +TX, Tetrachlorantraniliprole +TX, Tetradifon +TX, Tetramethrin +TX, Tetramethylfluthrin +TX, Tetranactin +TX, Tetraniliprole +TX, Theta-Cypermethrin +TX, Thiacloprid +TX, Thiamethoxam +TX, Thiocyclam +TX, Thiodicarb +TX, Thiofanox +TX, Thiometon +TX, Thiosultap +TX, Tigolaner +TX, Thiolantraniliprole +TX, Thioxazaphene +TX, Tolfenpyrad +TX, Toxaphene +TX, Tralomethrin + TX, transfluthrin + TX, triazamate + TX, triazophos + TX, trichlorfon + TX, trichloronate + TX, trichlorfon + TX, trifluenfuronate + TX, triflumezopyrim + TX, cyclopyrazoflor + TX, zeta-cypermethrin + TX, seaweed extract and fermented product from Melasse + TX, seaweed extract and fermented product from Melasse containing urea + TX, amino acids + TX, potassium and molybdenum and EDTA-chelated manganese + TX, seaweed extract and fermented plant product + TX, seaweed extract and fermented plant product containing plant hormones + TX, vitamins + TX, EDTA-chelated copper + TX, zinc + TX, and iron + TX, azadirachtin + TX, Bacillus aizawai (Bacillus aizawai + TX, Bacillus chitinosporus AQ746 (NRRL accession number B-21618) + TX, Bacillus firmus + TX, Bacillus kurstaki + TX, Bacillus mycoides AQ726 (NRRL accession number B-21664) + TX, Bacillus pumilus (NRRL accession number B-30087) + TX, Bacillus pumilus AQ717 (NRRL accession number B-21662) + TX, Bacillus sp.) AQ178 (ATCC accession number 53522) + TX, Bacillus sp. AQ175 (ATCC accession number 55608) + TX, Bacillus sp. AQ177 (ATCC accession number 55609) + TX, Bacillus subtilis unspecified + TX, Bacillus subtilis AQ153 (ATCC accession number 55614) + TX, Bacillus subtilis AQ30002 (NRRL accession number B-50421) + TX, Bacillus subtilis AQ30004 (NRRL accession number B-50455) + TX, Bacillus subtilis AQ713 (NRRL accession number B-21661) + TX, Bacillus subtilis AQ743 (NRRL accession number B-21665) + TX, Bacillus thuringiensis AQ52 (NRRL accession number B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL accession number B-21530) + TX, Bacillus thuringiensis subspec. kurstaki BMP123 + TX, Beauveria bassiana + TX, D-limonene + TX, granulovirus + TX, harpin + TX, Helicoverpa armigera armigera nucleopolyhedrovirus + TX, Helicoverpa zea nucleopolyhedrovirus + TX, Heliothis virescens nucleopolyhedrovirus + TX, Heliothis punctigera nucleopolyhedrovirus + TX, Metarhizium spp.) + TX, Muscodor albus 620 (NRRL accession number 30547) + TX, Muscodor roseus A3-5 (NRRL accession number 30548) + TX, Neem tree-based products + TX, Paecilomyces fumosoroseus + TX, Paecilomyces lilacinus + TX, Pasteuria nishizawae + TX, Pasteuria penetrans + TX, Pasteuria ramosa + TX, Pasteuria thornei + TX, Pasteuria usugae usgae + TX, P-cymene + TX, Plutella xylostella granulosis virus + TX, Plutella xylostella nucleopolyhedrovirus + TX, polyhedrovirus + TX, pyrethrum + TX, QRD420 (terpenoid blend) + TX, QRD452 (terpenoid blend) + TX, QRD460 (terpenoid blend) + TX, Quillaja saponaria + TX, Rhodococcus globerulus AQ719 (NRRL accession number B-21663) + TX, Spodoptera frugiperda nucleopolyhedrovirus + TX, Streptomyces gallus galbus (NRRL accession number 30232) + TX, Streptomyces sp. (NRRL accession number B-30145) + TX, terpenoid blend + TX, and Verticillium spp. + TX; an algicide selected from the group of substances consisting of bethoxadin [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, sibutrin [CCN] + TX, dichloron (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX; an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, cyclobutrifluram + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX; an avian repellent selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX; 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, dodisin (1112) + TX, fenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargafen (alternative name) [CCN] + T a fungicide selected from the group of substances consisting of X, 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, tecloftalam (766) + TX, and thiomersal (alternative name) [CCN] + TX; Adoxophyes orana GV (alternate name) (12) + TX, Agrobacterium radiobacter (alternate name) (13) + TX, Amblyseius spp. (alternate name) (19) + TX, Anagrapha falcifera NPV (alternate name) (28) + TX, Anagrus atomus (alternate name) (29) + TX, Aphelinus abdominalis (alternate name) (33) + TX, Aphidius colemani (alternate name) (34) + TX, Aphidoletes aphidimyza (alternate name) (35) + TX, Autographa californica californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (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 subsp. japonensis) (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (Bacillus thuringiensis subsp.tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternate name) (53) + TX, Beauveria brongniartii (alternate name) (54) + TX, Chrysoperla carnea (alternate name) (151) + TX, Cryptolaemus montrouzieri (red ladybird beetle) (alternate name) (178) + TX, Cydia pomonella GV (alternate name) (191) + TX, Dacnusa sibirica (alternate name) (212) + TX, Diglyphus isaea (alternate name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternate name) (300) + TX, Helicoverpa zea NPV (alternate name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternate name) (433) + TX, Hippodamia convergens (alternate name) (442) + TX, Leptomastix dactylopii (alternate name) (488) + TX, Macrolophus caliginosus (alternate name) (491) + TX, Mamestra brassicae brassicae NPV (alternate name) (494) + TX, Metaphycus helvolus (alternate name) (522) + TX, Metarhizium anisopliae var. acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. leconti (N.lecontei NPV (alternate name) (575) + TX, Orius spp. (alternate name) (596) + TX, Paecilomyces fumosoroseus (alternate name) (613) + TX, Phytoseiulus persimilis (alternate name) (644) + TX, Spodoptera exigua multicapsid nucleopolyhedrovirus (scientific name) (741) + TX, Steinernema bibionis (alternate name) (742) + TX, Steinernema carpocapsae (alternate name) (742) + TX, Steinernema felziae feltiae (alternate name) (742) + TX, Steinernema glaseri (alternate name) (742) + TX, Steinernema riobrave (alternate name) (742) + TX, Steinernema riobravis (alternate name) (742) + TX, Steinernema scapterisci (alternate name) (742) + TX, Steinernema spp. (alternate name) (742) + TX, Trichogramma spp. (alternate name) (826) + TX, Typhlodromus occidentalis a biological agent selected from the group of substances consisting of Verticillium lecanii (alternative name) (848) + TX; a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX; chemical disinfectants selected from the group of substances consisting of Apholate [CCN] + TX, Visadyl (alternative name) [CCN] + TX, Busulfan (alternative name) [CCN] + TX, Diflubenzuron (250) + TX, Dimatif (alternative name) [CCN] + TX, Hemel [CCN] + TX, Hempa [CCN] + TX, Metepa [CCN] + TX, Methiotepa [CCN] + TX, Methyl Apholate [CCN] + TX, Morzide [CCN] + TX, Penfluron (alternative name) [CCN] + TX, Tepa [CCN] + TX, Thiohempa (alternative name) [CCN] + TX, Thiotepa (alternative name) [CCN] + TX, Tretamine (alternative name) [CCN] and Uredepa (alternative name) [CCN] + TX; (E)-Deca-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-4,1 0-Dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-Dodec-7-en-1-yl acetate (IUPAC name) (285) + TX, (Z)-Hexadec-11-enal (IUPAC name) (436) + TX, (Z)-Hexadec-11-en-1-yl acetate (IUPAC name) (437) + TX, (Z)-Hex Sadec-13-en-11-yn-1-yl acetate (IUPAC name) (438) + TX, (Z)-Icos-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)-Tetradeca-9-en-1-yl acetate (IUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283) + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9Z,12E)-tetradeca-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 (alternative name) [CCN] + TX, Brevicomin (alternative name) [CCN] + TX, Codrelure (alternative name) [CCN] + TX, Codlemone (alternative name) (167) + TX, Cure (alternative name) (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 (alternative name) [CCN] + TX, Ethyl 4-methyloctanoate (IUPAC name) (317) + TX, Eugenol (alternative name) [CCN] + TX, Frontalin (alternative name) [CCN] + T X, a 1:1 mixture of the (Z,E) and (Z,Z) isomers of Gossyplure® (alternative name: hexadeca-7,11-dien-1-yl-acetate) (420) + TX, Grandolure (421) + TX, Grandolure I (alternative name) (421) + TX, Grandolure II (alternative name) (421) + TX, Grandolure III (alternative name) (421) + TX, Grandolure IV (alternative name) (421) + TX, Hexalure [CCN] + TX, Ipsdienol (alternative name) [CCN] + TX, Ipsenol (alternative name) [CCN] + TX, Japonirua (alternative name) (481) + TX, Lineatin (alternative name) [CCN] + TX, Litirua (alternative name) [CCN] + TX, Lupulua (alternative name) [CCN] + TX, Medurua [CCN] + TX, Megatomoic acid (alternative name) [CCN] + TX, Methyleugenol (alternative name) (540) + TX, Muscalua (563) + TX, Octadeca-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, Octadeca-3,13-Dien-1-yl acetate (IUPAC name) (589) + TX, Olfrulure (alternative name) [CCN] + TX, Orictalure (alternative name) (317) + TX, Ostramon (alternative name) [CCN] + TX, Siglua [CCN] + TX, Soldigin (alternative name) (736) + TX, Sulcatol (alternative name) [CCN] + TX, Tetradec-11-en-1-yl acetate (IU an insect pheromone selected from the group of substances consisting of Trimedulla (PAC name) (785) + TX, Trimedulla (839) + TX, Trimedulla A (alternate name) (839) + TX, Trimedulla B1 (alternate name) (839) + TX, Trimedulla B2 (alternate name) (839) + TX, Trimedulla C (alternate name) (839) and Trunk-call (alternate name) [CCN] + TX; an insect repellent selected from the group of substances 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, diethyltoluamide [CCN] + TX, dimethylcarbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX; Bis(tributyltin)oxide (IUPAC name) (913) + TX, Bromoacetamide [CCN] + TX, Calcium arsenate [CCN] + TX, Cloethocarb (999) + TX, Copper acetarsenite [CCN] + TX, Copper sulfate (172) + TX, Fentin (347) + TX, Ferric phosphate (IUPAC name) (352) + TX, Metaldehyde (518) + TX, Methiocarb (530) + TX, Niclosamide (576) + TX, Niclosamide-olamine (576) + TX, Pentachloroethylene (Phenylalanine) a molluscicide selected from the group of substances consisting of: chlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, thazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprole [394730-71-3] + TX; 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) (1065) + TX, 3-(4-chlorophenyl) -5-Methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprole [CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, AZ60541 (compound code) + TX, benclotiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, Cadusafos (109) + TX, Carbofuran (118) + TX, Carbon Disulfide (945) + TX, Carbosulfan (119) + TX, Chloropicrin (141) + TX, Chlorpyrifos (145) + TX, Cloetocarb (999) + TX, Cyclobutrifluram + TX, Cytokinin (alternative name) (210) + TX, Dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, Diamidafos (1044) + TX, Diclofenthion (1051) + TX, Dicrifos (alternative name) + TX, Dimethoate (262) + T X, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ethoprophos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpyrad (alternative name) + TX, fensulfothion (1158) + TX, fosthiazate (408) + TX, fostietan (1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX,Iodomethane (IUPAC name) (542) + TX, Isamidophos (1230) + TX, Isazophos (1231) + TX, Ivermectin (alternative name) [CCN] + TX, Kinetin (alternative name) (210) + TX, Mecarfone (1258) + TX, Metam (519) + TX, Metam-potassium (alternative name) (519) + TX, Metam-sodium (519) + TX, Methyl bromide (537) + TX, Methyl isothiocyanate (543) + TX, Milbemycin oxime (alternative name) [CCN] + TX, Moxidectin (alternative name [CCN] + TX, Myrothecium verrucaria) Composition (alternative name) (565) + TX, NC-184 (compound code) + TX, Oxamyl (602) + TX, Phorate (636) + TX, Phosphamidon (639) + TX, Phosphocarb [CCN] + TX, Cebufos (alternative name) + TX, Selamectin (alternative name) [CCN] + TX, Spinosad (737) + TX, Terbam (alternative name) + TX, Terbufos (773) + TX, Tetrachlorothiophene (IUP a nematicide selected from the group of substances consisting of AC / Chemical Abstracts Name) (1422) + TX, Thiafenox (alternative name) + TX, Thionazine (1434) + TX, Triazophos (820) + TX, Triazuron (alternative name) + TX, Xylenol [CCN] + TX, YI-5302 (compound code) and Zeatin (alternative name) (210) + TX, Fluensulfone [318290-98-1] + TX, Fluopyram + TX; a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX; a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX; 2-Isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, anthracene (880) + TX, arsenic trioxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, brodifacoium (89) + TX, bromadiolone (including alpha-bromadiolone) +TX, Bromethalin (92) +TX, Calcium cyanide (444) +TX, Chloralose (127) +TX, Chlorophacinone (140) +TX, Cholecalciferol (alternative name) (850) +TX, Coumacrol (1004) +TX, Coumafuryl (1005) +TX, Coumatetralyl (175) +TX, Crimidine (1009) +TX, Difenacoum (246) +TX, Difethialone (249) +TX, Diphacinone (273) +TX, Ergocalciferol (301) +TX, Flo Coumaphene (357) + TX, Fluoroacetamide (379) + TX, Flupropaline (1183) + TX, Flupropaline Hydrochloride (1183) + TX, gamma-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, Norbormide (1318) + TX, Fosacetim (1336) + TX, Fosacetim a rodenticide selected from the group of substances consisting of sphingosine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, sciliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX; a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol and nerolidol (alternative names) (324) + TX, MB-599 (development code) (498) + TX, MGK264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piperotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesamolin (1394) and sulfoxide (1406) + TX; an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [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, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN], and ziram (856) + TX; a virucidal agent selected from the group of substances consisting of Imanin (alternative name) [CCN] and Ribavirin (alternative name) [CCN] + TX; a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octilinone (590) and thiophanate-methyl (802) + TX; 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenylphenylsulfone + TX, acetoprole + TX, aldoxicarb + TX, amidithione + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, alamite + TX, arsenic oxide + TX, azobenzene + TX, azotoate + TX, benomyl + TX, benoxaphos + TX, ben Dibenzoate + TX, Bixafen + TX, Brofenvalerate + TX, Bromocyclen + TX, Bromophos + TX, Bromopropylate + TX, Buprofezin + TX, Butocarboxim + TX, Butoxycarboxim + TX, Butylpyridaben + TX, Calcium polysulfide + TX, Camphechlor + TX, Carbanolate + TX, Carbophenothion + TX, Cimiazol + TX, Thiomethionate + TX, Chlorbeside + TX, Chlordimeform + TX, Chlordimeform hydrochloride + TX, Chlorphenetole + TX, Chlor Fenson +TX, Chlorphenesulfide +TX, Chlorobenzilate +TX, Chlormebform +TX, Chlormethiuron +TX, Chloropropylate +TX, Chlorthiophos +TX, Cinerin I +TX, Cinerin II +TX, Cinerins +TX, Closantel +TX, Coumaphos +TX, Crotamiton +TX, Crotoxyphos +TX, Kufraeb +TX, Cyanthoate +TX, DCPM +TX, DDT +TX, Demefion +TX, Demefion-O +TX, Demefion-S +TX, Demeton-methyl +TX, Demeton-O +TX, Demeton- O-Methyl + TX, Demeton-S + TX, Demeton-S-methyl + TX, Demeton-S-methyl sulfone + TX, Dichlofluanid + TX, Dichlorvos + TX, Dicrifos + TX, Dienochlor + TX, Dimefox + TX, Zinex + TX, Zinex-Diclexin + TX, Dinocap-4 + TX, Dinocap-6 + TX, Dinocton + TX, Dinopenton + TX, Dinosulfone + TX, Dinotervon + TX, Dioxathion + TX, Diphenylsulfone + TX, Disulfiram + TX, DNOC + TX, Dofenapine + TX, Doramectin + TX,Endothion + TX, Epirinomectin + TX, Ethoate-methyl + TX, Etrimphos + TX, Fenazaflor + TX, Fenbutatin oxide + TX, Fenothiocarb + TX, Fenpyrad + TX, Fen-pyroximate + TX, Fenpyrazamine + TX, Fenson + TX, Fentrifanil + TX, Flubenzimine + TX, Flucycloxuron + TX, Fluenethyl + TX, Fluorobenside + TX, FMC 1137+TX, formetanate+TX, formetanate hydrochloride+TX, formparanate+TX, gamma-HCH+TX, gliodin+TX, halfenprox+TX, hexadecylcyclopropanecarboxylate+TX, isocarbophos+TX, jasmolin I+TX, jasmolin II+TX, jodofenphos+TX, lindane+TX, malonoven+TX, mecarbam+TX, mefosfolan+TX, mesulfen+TX, methacrifos+TX, methyl bromide+TX, metolcarb+TX, mexacarbate+TX, milbemycin oxime+TX, mipafox+TX, monocrotophos+TX, morphothion+TX, moxidectin+TX, Naled + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, Nifluridide + TX, Nikkomycin + TX, Nitrilacarb + TX, Nitrilacarb 1:1 zinc chloride complex + TX, Omethoate + TX, Oxydeprophos + TX, Oxydisulfoton + TX, pp'-DDT + TX, Parathion + TX, Permethrin + TX, Fenkapton + TX, Phosalone + TX, Phosphorane + TX, Phosphamidon + TX, Polychloroterpenes + TX, Polynactin + TX, Proclonol + TX, Promacyl + TX, Propoxur + TX, Protidathion + TX, Prothoate + TX, Pyrethrin I + TX, Pyrethrin II + TX , pyrethrins + TX, pyridaphenthion + TX, pirimitate + TX, quinalphos + TX, quinthiofos + TX, R-1492 + TX, phosglycine + TX, rotenone + TX, shladan + TX, cebufos + TX, selamectin + TX, sofamid + TX, SSI-121 + TX, sulfiram + TX, sulfuramide + TX, sulfotep + TX, sulfur + TX, diflobidazin + TX, tau-fluvalinate + TX, TEPP + TX, terbam + TX, tetradifon + TX, tetrasul + TX, thiafenox + TX, thiocarboxim + TX, thiofanox + TX, thiometon + TX, thioquinox + TX, thuringiensin + TX, triamiphos + TX, triatene + TX, triazophos + TX, Triazuron + TX, Trifenofos + TX, Trinactin + TX, Vamidothion + TX, Vaniliprole + TX, Bethoxazin + TX, Copper dioctanoate + TX, Copper sulfate + TX, Sibutrin + TX, Dichlorn + TX, Dichlorophen + TX, Endothal + TX, Fentin + TX, Slaked lime + TX, Nabam + TX, Quinoclamine + TX, Quinoneamide + TX, Simazine + TX, Triphenyltin acetate + TX, Triphenyltin hydroxide + TX, Crufomate + 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)benzene Sulfonamides + TX, 8-hydroxyquinoline sulfate + TX, Bronopol + TX, Copper hydroxide + TX, Cresol + TX, Dipyrithione + TX, Doditin + TX, Fenaminosulf + TX, Formaldehyde + TX, Hydralgafen + TX, Kasugamycin + TX, Kasugamycin hydrochloride hydrate + TX, Nickel bis(dimethyldithiocarbamate) + TX, Nitrapyrin + TX, Octilinone + TX, Oxolinic acid + TX, Oxytetracycline + TX, Hydroxyquinoline potassium sulfate + TX, Probenazole + TX, Streptomycin + TX, Streptomycin sesquisulfate + TX, Tecloftalam + TX, Thiomersal + TX, Adoxophyes orana GV+TX, Agrobacterium radiobacter+TX, Amblyseius spp.+TX, Anagrapha falcifera NPV+TX, Anagrus atomus+TX, Aphelinus abdominalis+TX, Aphidius colemani+TX, Aphidoletes aphidimyza+TX, Autographa californica NPV+TX, Bacillus sphaericus Neide+TX,Beauveria brongniartii + TX, Chrysoperla carnea + TX, Cryptolaemus montrouzieri + TX, Codling moth (Cydia pomonella) GV + TX, Dacnusa sibirica + TX, Diglyphus isaea + TX, Encarsia formosa + TX, Eretmocerus eremicus + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hippodamia convergens convergens + TX, Fuji bark wasp (Leptomastix dactylopii) + TX, Macrolophus caliginosus + TX, Armyworm moth (Mamestra brassicae) NPV + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, pine sawfly (Neodiprion sertifer) NPV and N. lecontei NPV + TX, Orius species spp.) + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX,Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Trichogramma spp. + TX, Typhlodromus occidentalis + TX, Verticillium lecanii) + TX, Apholate + TX, Visadil + TX, Busulfan + TX, Dimatif + TX, Hemel + TX, Hempa + TX, Metepa + TX, Methiotepa + TX, Methyl Apholate + TX, Molzide + TX, Penfluron + TX, Tepa + TX, Thiohempa + TX, Thiotepa + TX, Tretamine + TX, Uredepa + TX, (E)-Deca-5-en-1-yl acetate and (E)-Deca-5-en-1-yl acetate ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-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)-icosa-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)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradec-9,11-dien-1-yl a acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one + TX, alpha-multistriatin + TX, Brevicomin + TX, Codrelle + TX, Codlemone + TX, Querle + TX, Disparlure + 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, Frontalin + TX, Grandolure + TX, Grandolure I + TX, Grandolure II + TX, Grandolure III + TX, Grandolure IV + TX, Hexalure + TX, Ipsdienol + TX, Ipsenol + TX, Japonilure + TX, Lineatin + TX, Littlea + TX, Looplure + TX, Medlarure + TX, Megatomoic acid + TX, Methyleugenol Nol + TX, Muscalua + TX, Octadeca-2,13-dien-1-yl acetate + TX, Octadeca-3,13-dien-1-yl acetate + TX, Olfuralua + TX, Orictalua + TX, Ostramon + TX, Siglua + TX, Soldigin + TX, Sulcatol + TX, Tetradec-11-en-1-yl acetate + TX, Trimedulua + TX, Trimedulua A + TX, Trimedulua B1 + TX, Trimedulua B2 + TX, Trimedulua C + TX, Trunc-call + TX, 2-(Octylthio)-Ethanol butyl phthalate + TX, butapyronoxyl + TX, butoxy(polypropylene glycol) + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, diethyl toluamide + TX, dimethylcarbate + TX, dimethyl phthalate + TX, ethyl hexanediol + TX, hexamide + TX, methoquin-butyl + TX, methyl neodecanoamide + TX, oxamate + TX, picaridin + TX, 1-dichloro-1-nitroethane + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)-ethane + TX, 1,2-dichloropropane Pan and 1,3-dichloropropene + TX, 1-bromo-2-chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)acetic acid ethyl + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethyl carbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX,2-Chlorovinyldiethylphosphate + TX, 2-imidazolidone + 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-yldimethylcarbamate + TX, 4-methyl(prop-2-ynyl)amino-3, 5-Xylylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate + TX, acetione + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, alixycarb + TX, α-ecdysone + TX, aluminum phosphide + TX, aminocarb + TX, anabasine + TX, atidathion + TX, azamethiphos + TX, Bacillus thuringiensis (Bacillus thuringiensis) delta-endotoxin +TX, barium hexafluorosilicate +TX, barium polysulfide +TX, bartholin +TX, Bayer 22 / 190 +TX, Bayer 22408 +TX, beta-cyfluthrin +TX, beta-cypermethrin +TX, bioethanomethrin +TX, biopermethrin +TX, bis(2-chloroethyl) ether +TX, borax +TX, bromfenvinphos +TX, bromo-DDT +TX, bufencarb +TX, butacarb +TX, butathiophos +TX, butonate +TX, calcium arsenate +TX, calcium cyanide +TX, carbon disulfide +TX, carbon tetrachloride +TX, cartap hydrochloride +TX, cetethoxybenzoate ... Vadim + TX, chlorbicyclen + TX, chlordane + TX, chlordecone + TX, chloroform + TX, chloropicrin + TX, chlorphoxim + TX, chlorprazophos + TX, cis-resmethrin + TX, cismethrin + TX, clocitrin + TX, copper acetoarsenite + TX, copper arsenate + TX, copper oleate + TX, chumithoate + TX, cryolite + TX, CS708 + TX, cyanofenphos + TX, cyanophos + TX, cicrethrin + TX, cithioate + TX, d-tetramethrin + TX, DAEP + TX, dazomet + TX, decarbofuran + TX, diamidaphos + TX, dikapton + TX, dichlorophenthion + TX, dicresyl + TX, dicyclanil + TX,Dieldrin + TX, diethyl 5-methylpyrazol-3-yl phosphate + TX, dilol + TX, dimefluthrin + TX, dimethane + TX, Dimethryn + TX, Dimethylvinphos + TX, Dimethylan + TX, Dinoprop + TX, Dinosam + TX, Dinoseb + TX, Diofenolan + TX, Dioxabenzophos + TX, Dicyclophos + TX, DSP + TX, Ecdysterone + TX, EI 1642 + TX, EMPC + TX, EPBP + TX, Ethyl Formate + TX, Ethylene Dibromide + TX, Dichloroethane + TX, Ethylene Oxide + TX, EXD + TX, Fenchlorphos + TX, Fenetacarb + TX, Fenitrothion + TX, Fenoxacrim + TX, Fenpyrithrin + TX, Fensulfothion + TX, Fenthion-Ethyl + TX, Flucofuron + TX, Fosmetyllan + TX, Fospirate + TX, Fos Thietane +TX, Furathiocarb +TX, Frethrin +TX, Guazatine +TX, Guazatine acetate +TX, Sodium tetrathiocarbonate +TX, Halfenprox +TX, HCH +TX, HEOD +TX, Heptachlor +TX, Heterofos +TX, HHDN +TX, Hydrogen cyanide +TX, Hikincarb +TX, IPSP +TX, Isazophos +TX, Isobenzane +TX, Isodrin +TX, Isofenphos +TX, Isolane +TX, Isoprothiolane +TX, Isoxa Thione + TX, larval hormone I + TX, larval hormone II + TX, larval hormone III + TX, Kelevan + TX, Kinoprene + TX, lead arsenate + TX, leptophos + TX, lilimphos + TX, ritidathion + TX, m-cumenylmethylcarbamate + TX, magnesium phosphide + TX, magidox + TX, mecarfone + TX, menasone + TX, mercurous chloride + TX, mesulfenphos + TX, metam + TX, metam-potassium + TX, metam-sodium + TX, methane sulfonate Phonyl + TX, Metocrotophos + TX, Methoprene + TX, Methotrin + TX, Methoxychlor + TX, Methyl isothiocyanate + TX, Methyl chloroform + TX, Methylene chloride + TX, Methoxadiazone + TX, Mirex + TX, Naphthalophos + TX, Naphthalene + TX, NC-170 + TX, Nicotine + TX, Nicotine sulfate + TX, Nithiazine + TX, Nornicotine + TX, O-5-Dichloro-4-iodophenyl O-ethylethylphosphonothioate + TX,O,O-Diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate + TX, O,O-Diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate + TX, O,O,O',O'-Tetrapropyldithiopyrophosphate + TX, Oleic acid + TX, para-dichlorobenzene + TX, parathion-methyl + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, PH60-38 + TX, fenkapton + TX, fosnichlor + TX, phosphine + TX, phoxim-methyl + TX, pyri Metaphos + TX, Polychlorodicyclopentadiene Isomers + TX, Potassium Arsenite + TX, Potassium Thiocyanate + TX, Precocene I + TX, Precocene II + TX, Precocene III + TX, Pyrimidophos + TX, Profluthrin + TX, Promecarb + TX, Prothiofos + TX, Pyrazophos + TX, Pyresmethrin + TX, Cassia + TX, Quinalphos-methyl + TX, Quinothione + TX, Lafoxanide + TX, Resmethrin + TX, Rotenone + TX, Kadethrin + TX, Riania + TX, Ryanodine + TX, Sabadila + TX, Shradan + TX , Cebufos + TX, SI-0009 + TX, Tiapronil + TX, Sodium arsenite + TX, Sodium cyanide + TX, Sodium fluoride + TX, Sodium hexafluorosilicate + TX, Pentachlorophenoxide sodium salt + TX, Sodium selenate + TX, Sodium thiocyanate + TX, Sulcofuron + TX, Sulcofuron-sodium + TX, Sulfuryl fluoride + TX, Sulprofos + TX, Tar oil + TX, Thazimcarb + TX, TDE + TX, Tebupirimfos + TX, Temephos + TX, Telarethrin + TX, Tetrachloroethane + TX , Cyclophos + TX, Thiocyclam + TX, Thiocyclam Hydrogen Oxalate + TX, Thionazine + TX, Thiosultap + TX, Thiosultap-Sodium + TX, Tralomethrin + TX, Transpermethrin + TX, Triazamate + TX, Trichlormethaphos-3 + TX, Trichloronat + TX, Trimethacarb + TX, Tolprocarb + TX, Triclopyricarb + TX, Triplene + TX, Veratridine + TX, Veratrine + TX, XMC + TX, Zetamethrin + TX, Zinc Phosphide + TX, Zolaprofos + TX, Meperfluthrin + TX,Tetramethylfluthrin + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, ferric phosphate + TX, niclosamide-olamine + TX, tributyltin oxide + TX, pyrimorph + TX, triphenmorph + TX, 1,2-dibromo-3-chloropropane + TX, 1,3-dichloropropene + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine + TX, benclothiaz + TX, cytokinin + TX, DCIP + TX, rufural + TX, isamidophos + TX, Kinetin +TX, Myrothecium verrucaria composition +TX, Tetrachlorothiophene +TX, Xylenol +TX, Zeatin +TX, Potassium ethylxanthate +TX, Acibenzolar +TX, Acibenzolar-S-methyl +TX, Reynoutria sachalinensis extract +TX, Alpha-chlorohydrin +TX, Anth +TX, Barium carbonate +TX, Bisthiosemi +TX, Brodifacoum +TX, Bromadiolone +TX, Bromethalin +TX, Chlorophacinone +TX, Cholecalciferol +TX, Coumarol +TX, Coumafuryl +TX, Coumatetralyl +TX, Crimidine +TX, Difenacoum +TX, Difethialone +TX, Diphacinone +TX, Ergocalciferol +TX, Flocouma Phen + TX, Fluoroacetamide + TX, Flupropazine + TX, Flupropazine Hydrochloride + TX, Norbormide + TX, Fosacetim + TX, Phosphate + TX, Pindone + TX, Pyrinuron + TX, Sciliroside + TX, Sodium Fluoroacetate + TX, Thallium Sulfate + TX, Warfarin + TX, 2-(2-Butoxyethoxy)ethyl Piperonylate + TX, 5-(1,3-Benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, Fa Lunesol and nerolidol +TX, Verbutin +TX, MGK264 +TX, Piperonyl butoxide +TX, Piprotal +TX, Propyl isomer +TX, S421 +TX, Sesamex +TX, Sesamolin +TX, Sulfoxide +TX, Anthraquinone +TX, Copper naphthenate +TX, Copper oxychloride +TX, Dicyclopentadiene +TX, Thiram +TX, Zinc naphthenate +TX, Ziram +TX, Imanin +TX, Ribavirin +TX, Chlorinconazide +TX, Oxidation Mercury(II) + TX, thiophanate-methyl + TX, azaconazole + TX, bitertanol + TX, bromuconazole + TX, cyproconazole + TX, difenoconazole + TX, diniconazole + TX, epoxiconazole + TX, fenbuconazole + TX, fluquinconazole + TX, flusilazole + TX, flutriafol + TX, furametpyr + TX, hexaconazole + TX, imazalil + TX, imibenconazole + TX, ipconazole + TX,Metconazole + TX, myclobutanil + TX, paclobutrazol + TX, pefurazoate + TX, penconazole + TX, prothioconazole + TX, pyrifenox + TX, prochloraz + TX, propiconazole + TX, pyrisoxazole + TX, simeconazole + TX, tebuconazole + TX, tetraconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, triticonazole + TX, ancymidol + TX, fenarimol + TX, nuarimol + TX, bupirimate + TX, dimethirimol + TX, Ethirimol + TX, Dodemorph + TX, Fenpropidin + TX, Fenpropimorph + TX, Spiroxamine + TX, Tridemorph + TX, Cyprodinil + TX, Mepanipyrim + TX, Pyrimethanil + TX, Fenpiclonil + TX, Fludioxonil + TX, Benalaxyl + TX, Furalaxyl + TX, -Metalaxyl- + TX, R-Metalaxyl + TX, Ofrace + TX, Oxadixyl + TX, Carbendazim + TX, Debacarb + TX, Fuberidazole + TX, Thiabendazole + TX, Chlozolinate + TX, Dichlozolin + TX, Miclozolin Clozolin + TX, Procymidone + TX, Vinclozolin + TX, Boscalid + TX, Carboxin + TX, Fenfuram + TX, Flutolanil + TX, Mepronil + TX, Oxycarboxin + TX, Penthiopyrad + TX, Thifluzamide + TX, Dodine + TX, Iminoctadine + TX, Azoxystrobin + TX, Dimoxystrobin + TX, Enestrobulin + TX, Phenaminestrobin + TX, Flufenoxystrobin + TX, Fluoxastrobin + TX, Kresoxim-methyl + TX, Metominostrobin + TX, Trifloxystrobin Robin + TX, Oryzastrobin + TX, Picoxystrobin + TX, Pyraclostrobin + TX, Pyrametstrobin + TX, Pyraoxystrobin + TX, Ferbam + TX, Mancozeb + TX, Maneb + ​​TX, Methiram + TX, Propineb + ​​TX, Zineb + ​​TX, Captafol + TX, Captan + TX, Fluorimide + TX, Folpet + TX, Tolylfluanid + TX, Bordeaux mixture + TX, Copper oxide + TX, Mancopper + TX, Oxine-copper + TX, Nitrothal-isopropyl + TX, Edifenphos + TX, Iprobenfos + TX,Phosdifen +TX, Turcophos-methyl +TX, Anilazine +TX, Benthiavalicarb +TX, Blasticidin-S +TX, Chloroneb +TX, Chlorothalonil +TX, Cyflufenamid +TX, Cymoxanil +TX, Diclocymet +TX, Diclomedine +TX, Dicloran +TX, Diethofencarb +TX, Dimethomorph +TX, Flumorph +TX, Dithianon +TX, Ethaboxam +TX, Etridiazole +TX, Famoxadone +TX, Fenamidon +TX, Fenoxanil +TX, Ferimzone +T X, fluazinam + TX, fluopicolide + TX, flusulfamide + TX, fluxapyroxad + TX, fenhexamid + TX, fosetyl-aluminum + TX, hymexazole + TX, iprovalicarb + TX, cyazofamid + TX, methasulfocarb + TX, metrafenone + TX, pencycuron + TX, phthalide + TX, polyoxin + TX, propamocarb + TX, pyribencarb + TX, proquinazid + TX, pyroquilon + TX, pyriophenone + TX, quinoxyfen + TX, quintozene + TX, tiadinil +TX, triazoxide +TX, tricyclazole +TX, triforine +TX, validamycin +TX, valifenalate +TX, zoxamide +TX, mandipropamide +TX, fluveneteram +TX, isopyrazam +TX, sedaxane +TX, benzovindiflupyr +TX, pydiflumetofen +TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide +TX, isoflucipram +TX, isotianil +TX, dipimethitrone +T X, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + 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-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-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, methoxystrobin (jiaxiangjunzhi) + TX, rubenmixianan + TX, diclobenthiazox + TX, mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + TX, 2-[2-fluoro-6-[(8-fluro[( N-(2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, oxathiapiproline + TX, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, pyraziflumide + TX, inpirfluxam + TX, turolprocarb + TX, mefentrifluconazole + 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-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonic acid + TX, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridaclomethyl + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 1-[2-[[1-(4-chloro (Z,2E)-5-[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, ametoctrazine + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyisothiazolinone + 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, ametoctrazine + TX, amisulbrom + TX, penflufen + TX, mino-N,3-dimethyl-pent-3-enamide + TX, florylpicoxamide + TX, fenpicoxamide + TX, tebufloquine + TX, ipulfenoquine + TX, quinofumelin + TX, isofetamide + TX, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate + TX (which may be prepared from the method described in WO 2020 / 056090), ...(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate + TX (which may be prepared from the method described in WO 2020 / 056090), methyl N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate + TX (which may be prepared from 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 (which may be prepared from 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 (which may be prepared from 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- 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide + TX (which may be prepared from 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, benzothiostrobin + TX, fenamacril + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, fluopyram + TX, flufenoxadiazam + TX, flutianil + TX, fluopimomide + TX, pyrapropoin + TX, picarbutrazox + 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-carboxamide + 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, Methyltetraprole + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine- 3-Carboxamide + TX, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol + TX, fluoxapiprolin + TX, enoxastrobin + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate + TX, methyl methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate + TX (these compounds can be prepared by the method described in WO 2020 / 079111), methyl (Z) -2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate + TX, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate + TX (these compounds can be prepared from the method described in WO 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-[[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, 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 + TX, Cumoxystrobin + TX, Chungcheongmycin (zh ongshengmycin) + TX, copper thiodiazole + TX, zinc thiazole + TX, amethotractin + TX, iprodione + TX, seboxylamine + TX; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[ 5-Bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds are disclosed in WO 2015 / 15 5075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-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-trifluoro 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-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline Phosphorus-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 + TX (these compounds can be prepared by the method described in WO 2017 / 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 methods described in WO 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]propanamide + TX, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX phenyl]phenyl]methyl]propanamide + 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]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + 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, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + 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 the methods described in WO 2017 / 055473, WO 2017 / 055469, 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-hydroxypropyl]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-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared by the method described in WO 2016 / 156290); (4-phenoxyphen N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzene (N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzene) with 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']dipyrrole-1,3,5,7(2H,6H)-tetrone with TX (this compound can be prepared by the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzene Carbothioamide + 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-enamide + TX (this compound can be prepared by the method described in WO 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 (3-methylisoxazol-5-yl)-[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 / 06 5414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + TX (this compound can be prepared by the method described in WO 2018 / 158365); 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]phenyl]acetamide + TX a biologically active agent selected from N-[(Z)-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-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared by the methods described in WO 2018 / 202428); Microorganisms including: Acinetobacter lwoffii + TX, Acremonium alternatum + TX, Acremonium cephalosporium + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternata + TX, Alternaria cassia + TX, cassia) + TX, Alternaria destruens (Smolder®) + TX, Ampelomyces quisqualis (AQ10®) + TX, Aspergillus flavus AF36 (AF36®) + TX, Aspergillus flavus NRRL21882 (Aflaguard®) + TX, Aspergillus spp.) + TX, Aureobasidium pullulans + TX, Azospirillum + TX, (MicroAZ® + TX, TAZO B®) + TX, Azotobacter + TX, Azotobacter chroocuccum (Azotomeal®) + TX, Azotobacter cysts (Bionatural Blooming Blossoms®) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinosporus strain CM-1 + TX, Bacillus chitinosporus strain AQ746+TX, Bacillus licheniformis strain HB-2 (Biostart™ Rhizoboost®)+TX, Bacillus licheniformis strain 3086 (EcoGuard®+TX, Green Releaf®)+TX, Bacillus circulans+TX. Bacillus firmus (BioSafe® +TX, BioNem-WP® +TX, VOTiVO®) +TX, Bacillus firmus strain I-1582 +TX, Bacillus macerans +TX, Bacillus marismortui +TX, Bacillus megaterium +TX, Bacillus mycoides strain AQ726 +TX, Bacillus papillae (Milky Spore Powder®) +TX, Bacillus pumilus spp. +TX, Bacillus pumilus strain GB34 (Yield Shield®) + TX, Bacillus pumilus strain AQ717 + TX, Bacillus pumilus strain QST 2808 (Sonata® + TX, Ballad Plus®) + TX, Bacillus spahericus (VectoLex®) + TX, Bacillus spp. + TX, Bacillus spp. strain AQ175 + TX, Bacillus spp. strain AQ177 + TX, Bacillus spp.) strain AQ178+TX, Bacillus subtilis strain QST 713 (CEASE®+TX, Serenade®+TX, Rhapsody®)+TX, Bacillus subtilis strain QST 714 (JAZZ®)+TX, Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis var. amyloliquefaciensamyloliquefaciens strain FZB24 (Taegro® +TX, Rhizopro®) +TX, Bacillus thuringiensis Cry2Ae +TX, Bacillus thuringiensis Cry1Ab +TX, Bacillus thuringiensis aizawai GC91 (Agree®) +TX, Bacillus thuringiensis israelensis (BMP123® +TX, Aquabac® +TX, VectoBac®) +TX, Bacillus thuringiensis kurstaki Bacillus thuringiensis kurstaki (Javelin® + TX, Deliver® + TX, CryMax® + TX, Bondide® + TX, Scutella WP® + TX, Turilav WP® + TX, Astuto® + TX, Dipel WP® + TX, Biobit® + TX, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain BD#32 ... thuringiensis strain AQ52+TX, Bacillus thuringiensis var. aizawai (XenTari®+TX, DiPel®)+TX, Bacteria spp.) (GROWMEND® +TX, GROWSWEET® +TX, Shootup®) +TX, Clavipacter michiganensis bacteriophage (AgriPhage®) +TX, Bakflor® +TX, Beauveria bassiana (Beaugenic® +TX, Brocaril WP®) +TX, Beauveria bassiana GHA (Mycotrol ES® +TX, Mycotrol O® +TX, BotaniGuard®) +TX, Beauveria brongniartii (Engerlingspilz® +TX, Schweizer Beauveria® +TX, Melocont®) +TX, Beauveria species (Beauveria spp.) + TX, Botrytis cineria + TX, Bradyrhizobium japonicum (TerraMax®) + TX, Brevibacillus brevis + TX, Bacillus thuringiensis tenebrionis (Novodor®) + TX, BtBooster + TX, Burkholderia cepacia (Deny® + TX, Intercept® + TX, Blue Circle®) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp.) + TX, Canadian thistle fungus (CBH Canadian Bioherbicide®) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oleophila strain O+. TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reukaufii + TX, Candida saitoana (Bio-Coat® + TX, Biocure®) + TX, Candida sake + TX, Candida spp. + TX, Candida tenius + TX, Cedecea dravisae + TX, Cellulomonas flavigena + TX, Chaetomium cochlioides cochliodes (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugae strain PRAA4-1T (Grandevo®) + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium chlorocephalum + TX, Cladosporium spp. + TX, Cladosporium tenuissimum + TX, Clonostachys rosea rosea) (EndoFine®) + TX, Colletotrichum acutatum + TX, Coniothyrium minitans (Cotans WG®) + TX, Coniothyrium spp.) + TX, Cryptococcus albidus (YIELDPLUS®) + TX, Cryptococcus humicola + TX, Cryptococcus infirmo-miniatus + TX, Cryptococcus laurentii + TX, Cryptophlebia leucotreta granulovirus (Cryptex®) + TX, Cupriavidus campinensis + TX, Cydia pomonella granulovirus (CYD-X®) + TX, Cydia pomonella granulovirus (Madex® + TX, Madex Plus® + TX, Madex Max / Carpovirusine®) + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum nigrum) + TX, Epicoccum purpurascens + TX, Epicoccum spp.) + TX, Filobasidium floriforme + TX, Fusarium acuminatum + TX, Fusarium chlamydosporum + TX, Fusarium oxysporum (Fusaclean® / Biofox C®) + TX, Fusarium proliferatum + TX, Fusarium spp. + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum (Primastop® + TX, Prestop®) + TX, Gliocladium roseum roseum + TX, Gliocladium spp. (SoilGard®) + TX, Gliocladium virens (Soilgard®) + TX, Granulovirus (Granupom®) + TX, Halobacillus halophilus + TX, Halobacillus litoralis + TX, Halobacillus trueperi + TX, Halomonas spp.) + TX, Halomonas subglaciescola + TX, Halovibrio variabilis + TX, Hanseniaspora uvarum + TX, Helicoverpa armigera nucleopolyhedrovirus (Helicovex®) + TX, Helicoverpa zea nucleopolyhedrovirus (Gemstar®) + TX, isoflavone-formononetin (Myconate®) + TX, Kloeckera apiculata + TX, Kloeckera spp.) + TX, Lagenidium giganteum (Laginex®) + TX, Greenhouse whitefly (Lecanicillium longisporum) (Vertiblast®) + TX, Lecanicillium muscarium (Vertikil®) + TX, Gypsy moth (Lymantria dispar) nucleopolyhedrovirus (Disparvirus®) + TX, Marinococcus halophilus + TX, Meira geulakonigii + TX, Metarhizium anisopliae (Met52®) + TX, Metarhizium anisopliae (Destruxin®) + TX, WP®) + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX, Micromonospora coerulea + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 (Muscudor®) + TX, Muscodor roseus strain A3-5 + TX, Mycorrhizae spp.) (AMykor® +TX, Root Maximizer®) +TX, Myrothecium verrucaria strain AARC-0255 (DiTera®) +TX, BROS PLUS® +TX, Ophiostoma piliferum strain D97 (Sylvanex®) +TX, Paecilomyces farinosus +TX, Paecilomyces fumosoroseus (PFR-97® +TX, PreFeRal®) +TX, Paecilomyces linacinus (Biostat WP®) +TX, Paecilomyces lilacinus strain 251 (MeloCon WG®) + TX, Paenibacillus polymyxa + TX, Pantoea agglomerans (BlightBan C9-1®) + TX, Pantoea spp. + TX, Pasteuria spp. (Econem®) + TX, Pasteuria nishizawae + TX, Penicillium aurantiogriseum + TX, Penicillium billai (Jumpstart® + TX, TagTeam®) + TX, Penicillium brevicompactum brevicompactum + TX, Penicillium frequentans + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp.) + TX, Penicillium viridicatum + TX, Phlebiopsis gigantea (Phlebiopsis. gigantean (Rotstop®) + TX, Phosphhomeal® + TX, Phytophthora cryptogea + TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp.) + TX, Pseudomonas syringae (Bio-Save®) + TX, Pseudomonas viridiflava + TX, Pseudomonas fluorescens (Zequanox®) + TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®) + TX, Puccinia canaliculata + TX, Puccinia thlaspeos (Wood Warrior®) + TX, Pythium paroecandrum + TX, Pythium oligandrum oligandrum (Polygandron® + TX, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizoctonia (Dormal® + TX, Vault®) + TX, 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, Sclerotinia minor + TX, Sclerotinia minor (SARRITOR®) + TX, Scytalidium spp. + TX, Scytalidium uredinicola + TX, Spodoptera exigua nuclear polyhedrosis virus (Spod-X® + TX, Spexit®) + TX, Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp.) + TX, Sordaria fimicola + TX, Spodoptera littoralis nuclear polyhedrosis virus (Littovir®) + TX, Sporobolomyces roseus + TX, Stenotrophomonas maltophilia + TX, Streptomyces ahygroscopicus + TX, Streptomyces albaduncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, Streptomyces griseoplanus griseoplanus + TX, Streptomyces griseoviridis (Mycostop®) + TX, Streptomyces lydicus (Actinovate®) + TX, Streptomyces lydicus WYEC-108 (ActinoGrow®) + TX, Streptomyces violaceus + TX, Tilletiopsis minor + TX, Tilletiopsis spp.) + TX, Trichoderma asperellum (T34 Biocontrol®) + TX, Trichoderma gamsii (Tenet®) + TX, Trichoderma atroviride (Plantmate®) + TX, Trichoderma hamatum TH 382 + TX, Trichoderma harzianum rifai (Mycostar®) + TX, Trichoderma harzianum T-22 (Trianum-P® + TX, PlantShield HC® + TX, RootShield® + TX, Trianum-G®) + TX, Trichoderma harzianum harzianum) T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma spp.) LC 52 (Sentinel®) + TX, Trichoderma lignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma taxi + TX, Trichoderma virens + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard®) + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier®) + TX, 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 (Botry-Zen®) + TX, Ustilago maydis + TX, various bacteria and supplemental micronutrients (Natural II®) + TX, various fungi (Millennium Microbes®) + TX, Verticillium chlamydosporium + TX, Verticillium lecanii lecanii (Mycotal® + TX, Vertalec®) + TX, Vip3Aa20 (VIPtera®) + TX, Virgibaclillus marismortui + TX, Xanthomonas campestris pv. Poae (Camperico®) + TX, Xenorhabdus bovienii + TX, Xenorhabdus nematophilus; Plant extracts including: pine oil (Retenol®) +TX, azadirachtin (Plasma), Neem Oil® +TX, AzaGuard® +TX, MeemAzal® +TX, Molt-X® +TX, botanical insect growth regulators (Neemazad® +TX, Neemix®) +TX, rapeseed oil (Lilly Miller Vegol®) +TX, American ant's weed (Chenopodium ambrosioides near ambrosioides) (Requiem®) +TX, Chrysanthemum extract (Crisant®) +TX, neem oil extract (Trilogy®) +TX, Labiatae essential oil (Botania®) +TX, clove, rosemary, peppermint, and thyme oil extracts (Garden insect killer®) + TX, glycine betaine (Greenstim®) + TX, garlic + TX, lemongrass oil (GreenMatch®) + TX, neem oil + TX, catnip (Nepeta cataria) (catnip oil) + TX, catnip (Nepeta catarina) + TX, nicotine + TX, oregano oil (MossBuster®) + TX, sesame (Pedaliaceae) oil (Nematon®) + TX, pyrethrum + TX, soapberry (Quillaja saponaria) (NemaQ®) + TX, giant knotweed (Reynoutria sachalinensis) (Regalia® + TX, Sakalia®) + TX, rotenone (Eco Roten®) + TX, Rutaceae extract (Soleo®) + TX, soybean oil (Ortho ecosense®) +TX, tea tree oil (Timorex Gold®) +TX, thyme oil +TX, AGNIQUE® MMF +TX, BugOil® +TX, a mixture of rosemary, sesame, peppermint, thyme and cinnamon extracts (EF300®) + TX, a mixture of clove rosemary and peppermint extracts (EF 400®) + TX, a mixture of clove peppermint garlic oil and mint (Soil Shot®) + TX, kaolin (Screen®) + TX, storage glucan from brown algae (Laminarin®); Pheromones, including: blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, codling moth pheromone (Paramount dispenser-(CM) / Isomate C-Plus®) + TX, grape berry moth pheromone (3M MEC-GBM Sprayable Pheromone®) + TX, leafroller pheromone (3M MEC-LR Sprayable Pheromone®) + TX, muscamone (Snip7 Fly Bait® + TX, Starbar Premium Fly Bait®) + TX, oriental fruit moth pheromone (3M oriental fruit moth sprayable pheromone®) + TX, peachtree Borer pheromone (Isomate-P®) + TX, Tomato Pinworm pheromone (3M Sprayable pheromone®) + TX, Entostat powder (palm tree extract) (Exosex CM®) + TX, (3E,8Z,11Z)-3,8,11-tetradecatrienyl 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, Scenturion® + TX, Biolure® + TX, Check-Mate® + TX, Lavandulyl senecioate + TX; Macroorganisms including: Aphelinus abdominalis + TX, Aphidius ervi (Aphelinus-System®) + TX, Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline® + TX, Andersoni-System®) + TX, Amblyseius californicus californicus (Amblyline® + TX, Spical®) + TX, Amblyseius cucumeris (Thripex® + TX, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline swirskii® + TX, Swirskii-Mite®) + TX, Amblyseius womersleyi (WomerMite®) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fusciventris fusciventris) + TX, Anagyrus kamali + TX, Anagyrus loecki + TX, Anagyrus pseudococcus (Anagyruspseudococci (Citripar®) + TX, Anicetus benefices + TX, Anisopteromalus calandrae + TX, Anthocoris nemoralis (Anthocoris-System®) + TX, Aphelinus abdominalis (Apheline® + TX, Aphiline®) + TX, Aphelinus asychis + TX, Aphidius colemani (Aphipar®) + TX, Aphidius ervi (Ervipar®) + TX, Aphidius gifuensis + TX, Aphidius matricariae matricariae (Aphipar-M®) + TX, Aphidoletes aphidimyza (Aphidend®) + TX, Aphidoletes aphidimyza (Aphidoline®) + TX, Aphytis lingnanensis + TX, Aphytis melinus + TX, Aprostocetus hagenowii + TX, Atheta coriaria (Staphyline®) + TX, Bombus spp. + TX, Bombus terrestris (Natupol Beehive® + TX, Bombus terrestris (Beeline® + TX, Tripol®) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, Chrysoperlacarnea (Chrysoline®) + TX, Chrysoperla carnea (Chrysopa®) + TX, Chrysoperla rufilabris + TX, Cirrospilus ingenuus + TX, Cirrospilus quadristriatus + TX, Citrostichus phyllocnistoides + TX, Closterocerus chamaeleon + TX, Closterocerus spp. + TX, Coccidoxenoides perminutus (Planopar®) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae + TX, Cryptolaemus montrouzieri (Cryptobug® + TX, Cryptoline®) + TX, Cybocephalus nipponicus (Dacnusa sibirica) + TX, Dacnusa sibirica (Minusa®) + TX, Diglyphus isaea (Diminex®) + TX, Delphastus catarinae (Delphastus catalinae) (Delphastus®) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudata + TX, Diaparsisjucunda + TX, Diaphorencyrtus aligarhensis + TX, Diglyphus isaea + TX, Diglyphus isaea (Miglyphus® + TX, Digline®) + TX, Dacnusa sibirica (DacDigline® + TX, Minex®) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max® + TX, Encarline® + TX, En-Strip®) + TX, Eretmocerus eremicus (Enermix®) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend®) + TX, Eretmoceris siphonini + TX, Eretmocerus californicus + TX, Eretmocerus eremicus (Ercal® + TX, Eretline e®) + TX, Eretmocerus eremicus (Bemimix®) + TX, Eretmocerus hayati + TX, Eretmocerus mundus mundus) (Bemipar® + TX, Eretline m®) + TX, Eretmocerus siphonini + TX, Exochomus quadripustulatus + TX, Feltiellaacarisuga (Spidend®) + TX, Feltiella acarisuga (Feltiline®) + TX, Fopius arisanus + TX, Fopius ceratitivorus + TX, formononetin (Wirless Beehome®) + TX, Franklinothrips vespiformis (Vespop®) + TX, Galendromus occidentalis + TX, Goniozus legneri + TX, Habrobracon hebetor + TX, Harmonia axyridis axyridis (HarmoBeetle®) + TX, Heterorhabditis spp. (Lawn Patrol®) + TX, Heterorhabditis bacteriophora (NemaShield HB® + TX, Nemaseek® + TX, Terranem-Nam® + TX, Terranem® + TX, Larvanem® + TX, B-Green® + TX, NemAttack® + TX, Nematop®) + TX, Heterorhabditis megidis (Nemasys H® + TX, BioNem H® + TX, Exhibitline hm® + TX, Larvanem-M®) + TX, Hippodamia convergens) + TX, Hypoaspis aculeifer (Aculeifer-System® + TX, Entomite-A®) + TX, Hypoaspis miles (Hypoline m® + TX, Entomite-M®) + TX, Lbalia leucospoides + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar®) + TX, Leptomastix epona + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Lucilia caesar (Natufly®) + TX, Lysiphlebus testacapes testaceipes + TX, Macrolophus caliginosus (Mirical-N® + TX, Macroline c® + TX, Mirical®) + TX, Mesoseiulus longipes + TX, Metaphycus flavus + TX, Metaphycus lounsburyi + TX, Micromus angulatus (Milacewing®) + TX, Microterys flavus + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®) + TX, Neodryinus typhlocybae) + TX, Miyako Phytoseiulus (Neoseiulus californicus) + TX, Neoseiulus cucumeris (THRYPEX®) + TX, Neoseiulus fallasis (Neoseiulusfallacis + TX, Nesideocoris tenuis (NesidioBug® + TX, Nesibug®) + TX, Ophyra aenescens (Biofly®) + TX, Orius insidiosus (Thripor-I® + TX, Oriline i®) + TX, Orius laevigatus (Thripor-L® + TX, Oriline l®) + TX, Orius majusculus (Oriline m®) + TX, Orius strigicollis (Thripor-S®) + TX, Pauesia juniperum (Pauesia juniperorum + TX, Pediobius foveolatus + TX, Phasmarhabditis hermaphrodita (Nemaslug®) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimilis (Spidex® + TX, Phytoline p®) + TX, Podisus maculiventris (Podisus®) + TX, Pseudacteon curvatus + TX, Pseudacteon obtusus + TX, Pseudacteon tricuspis tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicana + TX, Psyllaephagus pilosuspilosus + TX, Psyttalia concolor (complex) + TX, Quadrastichus spp. + TX, Rhyzobius lophanthae + TX, Rodolia cardinalis + TX, Rumina decollate + TX, Semielacher petiolatus + TX, Sitobion avenae (Ervibank®) + TX, Steinernema carpocapsae (Nematac C® + TX, Millennium® + TX, BioNem C®+TX, NemAttack®+TX, Nemastar®+TX, Capsanem®+TX, Steinernema feltiae (NemaShield®+TX, Nemasys F®+TX, BioNem F®+TX, Steinernema-System®+TX, NemAttack®+TX, Nemaplus®+TX, Exhibitline sf®+TX, Scia-rid®+TX, Entonem®)+TX, Steinernema kraussei (Nemasys L®+TX, BioNem L®+TX, Exhibitline srb®)+TX, Steinernema riobrave riobrave (BioVector® + TX, BioVektor®) + TX, Steinernema scapterisci (Nematac S®) + TX, Steinernema spp. + TX, Steinernema spp. (Guardian Nematodes®) + TX, Stethorus punctilumpunctillum (Stethorus®) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae (Tricholine b®) + TX, Trichogramma brassicae (Tricho-Strip®) + TX, Trichogramma evanescens + TX, Trichogramma minutum + TX, Trichogramma ostriniae + TX, Trichogramma pratoneri platneri + TX, Trichogramma pretiosum + TX, Xanthopimpla stemmator + TX; Other biological agents include: abscisic acid +TX, bioSea® +TX, Chondrostereum purpureum (Chontrol Paste®) +TX, Colletotrichum gloeosporioides (Collego®) +TX, copper octanoate (Cueva®) +TX, delta traps (Trapline d®) +TX, Erwinia amylovora (Harpin) (ProAct® +TX, Ni-HIBIT Gold CST®) +TX, fatty acids derived from natural by-products of extra virgin olive oil (FLIPPER®) +TX, ferric phosphate (Ferri-phosphate) (Ferramol®) +TX, funnel traps (Trapline y®) +TX, Gallex® +TX, Grower's Secret® +TX, Homo-brassonolide +TX, Iron phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait®) +TX, MCP hail trap (Trapline f®) +TX, Microctonus hyperodae +TX, Mycoleptodiscus terrestris (Des-X®) +TX, BioGain® +TX, Aminomite® +TX, Zenox® +TX, pheromone trap (Thripline ams®) + TX, potassium bicarbonate (MilStop®) + TX, potassium salts of fatty acids (Sanova®) + TX, potassium silicate solution (Sil-Matrix®) + TX, potassium iodide + potassium thiocyanate (Enzicur®) + TX, SuffOil-X® + TX, spider venom + TX, Nosema locustae (Semaspore Organic Grasshopper)Control®) + TX, sticky traps (Trapline YF® + TX, Rebell Amarillo®) + TX and traps (Takitrapline y+b®) + TX; (1) an antibacterial agent selected from the group consisting of: (1.1) Examples of such bacteria are: Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.) (WO 2013 / 034938) + TX; Bacillus pumilus, in particular the strain BU F-33 with NRRL accession number 50185 (available as part of the CARTISSA® range from BASF, EPA registration number 71840-19) + TX; Bacillus subtilis, in particular the strain QST713 / AQ713 (SERENADE OPTI or SERENADE OPTI® from Bayer CropScience LP, US). No. 6,060,051 (available as ASO, NRRL accession number B21661) +TX; Bacillus subtilis strain BU1814 (available as VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA from BASF SE) +TX; Bacillus subtilis var. amyloliquefaciens strain FZB24 (available as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5) from Novozymes) +TX, with accession number DSM10271 +TX; Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.) +TX; Bacillus sp. sp.), in particular strain D747 (available as DOUBLE NICKEL® from Kumiai Chemical Industry Co., Ltd.), having accession number FERM BP-8234, U.S. Pat. No. 7,094,592+TX; Paenibacillus sp., having accession number NRRL B-50972 or accession number NRRL B-67129) strain, WO 2016 / 154297 +TX; Paenibacillus polymyxa, in particular strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) +TX; Pantoea agglomerans, in particular strain E325 (accession number NRRL B-21856) (available as BLOOMTIME BIOLOGICAL™ FD BIOPESTICIDE from Northwest Agri Products) +TX; Pseudomonas proradix from Sourcon Padena (e.g., PRORADIX®) +TX; and (1.2) Examples are fungi: Aureobasidium pullulans, in particular blastospores of the strain DSM 14940, blastospores of the strain DSM 14941 or a mixture of blastospores of the strains DSM 14940 and DSM 14941 (for example BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, CH) + TX; Pseudozyma aphidis (disclosed in WO 2011 / 151819 by Yissum Research Development Company of the Hebrew University of Jerusalem) + TX; Saccharomyces cerevisiae cerevisiae), in particular the strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 (disclosed in WO 2010 / 086790 from Lesaffre et Compagnie, FR) + TX; (2) A biological bactericide or fungicide selected from the following group: (2.1) Examples are bacteria such as: Agrobacterium radiobacter strain K84 (e.g., GALLTROL-A® from AgBioChem, CA) + TX; Agrobacterium radiobacter strain K1026 (e.g., NOGALL® from BASF SE) + TX; Bacillus subtilis var. amyloliquefaciens strain FZB24 with accession number DSM10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) + TX; Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel™ from Kumiai Chemical Industry Co., Ltd., with accession number FERM BP-8234, U.S. Pat. No. 7,094,592) +TX; Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL accession number B-50768, WO 2014 / 028521) (STARGUS® from Marrone Bio Innovations) +TX; Bacillus amyloliquefaciens strain FZB42, accession number DSM 23117 (available as RHIZOVITAL® from ABiTEP, DE) +TX; Bacillus amyloliquefaciens isolate B246 (e.g. AVOGREEN™ from the University of Pretoria) +TX; Bacillus licheniformis, in particular strain SB3086 with accession number ATCC 55406, WO 2003 / 000051 (available as ECOGUARD™ Biofungicide and GREEN RELEAF™ from Novozymes) +TX +TX;Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation) + TX; Bacillus methylotrophicus strain BAC-9912 (from the Chinese Academy of Sciences' Institute of Applied Ecology) + TX; Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.) (WO 2013 / 034938) + TX; Bacillus mycoides mycoides, isolate, having accession number B-30890 (available from Certis USA LLC, a subsidiary of Mitsui & Co., Ltd., as BMJ TGAI® or WG and LifeGard®) +TX; Bacillus pumilus, particularly strain QST2808 (available from Bayer CropScience LP, US as SONATA®, having accession number NRRL B-30087, and described in U.S. Pat. No. 6,245,551) +TX; Bacillus pumilus, particularly strain GB34 (available from Bayer AG, DE as Yield Shield®) +TX; Bacillus pumilus, particularly strain BU, having NRRL accession number 50185 F-33 ​​(available as part of the CARTISSA product line from BASF, EPA registration number 71840-19) + TX; Bacillus subtilis, specifically strain QST713 / AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, with NRRL accession number B21661, as described in U.S. Pat. No. 6,060,051) + TX;Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan as BIOBAC® WP, registered in Taiwan as a biological fungicide under registration numbers 4764, 5454, 5096, and 5277) +TX; Bacillus subtilis strain MBI 600 (available from BASF SE as SUBTILEX), having accession number NRRL B-50595, U.S. Pat. No. 5,061,495 +TX; Bacillus subtilis strain GB03 (available from Bayer AG, DE as Kodiak®) +TX; Bacillus subtilis strain BU1814 (available from BASF SE as VELONDIS® PLUS; Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.) + TX; Bacillus subtilis KTSB strain (FOLIACTIVE® from Donaghys) + TX; Bacillus subtilis IAB / BS03 (AVIV® from STK Bio-Ag Technologies, PORTENTO® from Idai Nature) + TX; Bacillus subtilis subtilis strain Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under registration numbers 4764, 5454, 5096, and 5277) +TX; Paenibacillus epiphyticus from BASF SE (WO 2016 / 020371) +TX; Paenibacillus polymyxa ssp. plantarum from BASF SE (WO 2016 / 020371) +TX; Paenibacillus sp. with accession number NRRL B-50972 or accession number NRRL B-67129.Pseudomonas chlororaphis strain AFS009, with accession number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER™ and ZIO™ from AgBiome Innovations, US) + TX; Pseudomonas chlororaphis, in particular strain MA342 (e.g., CEDOMON™, CERALL™ and CEDRESS™ from Bioagri and Koppert) + TX; Pseudomonas fluorescens strain A506 (e.g., BLIGHTBAN™ A506 from NuFarm) + TX; Pseudomonas proradix (e.g., Sourcon™). PRORADIX® from Padena) + TX; Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (Accession number DSM7206) (MYCOSTOP® from Verdera, PREFENCE® from BioWorks, see Crop Protection 2006, 25, 468-475) + TX; Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (ACTINO-IRON® and ACTINOVATE® from Novozymes) + TX; and (2.2) Examples of fungi are: Ampelomyces quisqualis, in particular the strain AQ 10 (for example AQ 10® from IntrachemBio Italia) + TX; Ampelomyces quisqualis strain AQ10 with accession number CNCM1-807 (for example AQ 10® from IntrachemBio Italia) + TX; Aspergillus flavus strain NRRL 21882 (product known as AFLA-GUARD® from Syngenta / ChemChina) + TX; Aureobasidium pullulans, in particular blastospores of the strain DSM 14940 + TX; Aureobasidium pullulans, in particular the strain DSM Aureobasidium pullulans, in particular a mixture of blastospores of strains DSM 14940 and DSM 14941 (e.g., Botector® by bio-ferm, CH) + TX; Chaetomium cupreum (accession number CABI 353812) (e.g., BIOKUPRUM® by AgriLife) + TX; Chaetomium globosum (available as RIVADIOM® by Rivale) + TX; Cladosporium cladosporioides, strain H39, with accession number CBS122244, as described in US Patent Application Publication No. 2010 / 0291039 (Stichting Dienst Landbouwkundig). Onderzoek)+TX; Coniothyrium minitans, In particular, strain CON / M / 91-8 (accession number DSM9660, e.g. Contans® from Bayer CropScience Biologics GmbH) + TX; Cryptococcus flavescens, strain 3C (NRRL Y-50378) (B2.2.99) + TX; Dactylaria Candida + TX; Dilophosphora alopecuri (available as TWIST FUNGUS®) + TX; Fusarium oxysporum, strain Fo47 (available as FUSACLEAN® from Natural Plant Protection) + TX; Gliocladium catenulatum (syn. Clonostachys rosea f. catenulata) + TX; rosea f. catenulate) strain J1446 (e.g. Prestop® by Lallemand) + TX;Gliocladium roseum (also known as Clonostachys rosea f rosea), particularly strain 321U from the fungus Adjuvants Plus, strain ACM941 disclosed by Xue (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 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 near commercial fungal antagonist Clonostachys rosea strain 'IK726', Australas Plant Pathol. 2007,36:95-101) +TX; Lecanicillium lecanii from strain KV01 Conidia of Metschnikowia fructicola (formerly known as Verticillium lecanii) (e.g. Vertalec® by Koppert / Arysta) +TX; Metschnikowia fructicola, in particular the strain NRRL Y-30752, (B2.2.3) +TX; Microsphaeropsis ochracea +TX; Muscodor roseus, in particular the strain A3-5 (accession number NRRL 30548) +TX; Penicillium steckii from BASF SE (DSM 27859, WO 2015 / 067800) +TX; Penicillium vermiculatum vermiculatum)+TX;Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from Danstar Ferment) +TX; Pichia anomala, strain WRL-076 (NRRL Y-30842), U.S. Pat. No. 7,579,183 +TX; Pseudozyma flocculosa, strain PF-A22 UL (available as SPORODEX® L from Plant Products Co., CA) +TX; Saccharomyces cerevisiae, specifically strain LASO2 (Agro-Levures et Derives), strain LAS117 cell wall (CEREVISANE® from Lesaffre, ROMEO® from BASF SE), Lesaffre et strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM No. 1-3939 from Compagnie, FR (WO 2010 / 086790) + TX; Simplicillium lanosoniveum + TX; Talaromyces flavus, strain V117b + TX; Trichoderma asperelloides JM41R (accession number NRRL B-50759) (TRICHO PLUS® from BASF SE) + TX; Trichoderma asperellum, in particular strain kd (e.g. T-Gro from Andermatt Biocontrol) + TX; Trichoderma asperellum asperellum), in particular the strain SKT-1, with the accession number FERM P-16510 (for example ECO-HOPE® from Kumiai Chemical Industry Co., Ltd.), the strain T34 (for example T34 Biocontrol from Biocontrol Technologies SL, ES) or the strain ICC 012+TX from Isagro;Trichoderma atroviride, in particular the strain SC1 (with accession number CBS 122089, WO 2009 / 116106 and US Pat. No. 8,431,120 (Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g. Sentinel from Agrimm Technologies Limited) + TX; Trichoderma atroviride, strain CNCM 1-1237 (e.g. Esquive® WP from Agrauxine, FR) + TX; Trichoderma atroviride, strain number V08 / 002387 + TX; Trichoderma atroviride atroviride, strain NMI number V08 / 002388+TX; Trichoderma atroviride, strain NMI number V08 / 002389+TX; Trichoderma atroviride, strain NMI number V08 / 002390+TX; Trichoderma atroviride, strain LC52 (e.g., Tenet by Agrimm Technologies Limited)+TX; Trichoderma atroviride, strain ATCC 20476 (IMI 206040)+TX; Trichoderma atroviride Trichoderma atroviride, strain T11 (IMI352941 / CECT20498) + TX; Trichoderma atroviride, strain SKT-1 (FERM P-16510), JP 11-253151 A + TX; Trichoderma atroviride, strain SKT-2 (FERM P-16511), JP 11-253151 A + TX; Trichoderma atroviride, strain SKT-3 (FERM P-17021), JP 11-253151 A + TX;Trichoderma fertile (e.g., the product TrichoPlus from BASF) +TX; Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151 CABI, e.g., BioDerma from AGROBIOSOL DE MEXICO, SADE CV) +TX; Trichoderma gamsii (formerly T. viride), strain ICC 080 (IMI CC 392151 CABI) (available as BIODERMA® from AGROBIOSOL DE MEXICO, SADE CV) +TX; Trichoderma harmatum +TX; Trichoderma harmatum with accession number ATCC 28012 harmatum + TX; Trichoderma harzianum strain T-22 (e.g. Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa SimbT5 (Simbiose Agro) + TX; Trichoderma harzianum + TX; Trichoderma harzianum rifai T39 (e.g. Trichodex® from Makhteshim, US) + TX; Trichoderma harzianum strain ITEM 908 (e.g. Trianum-P from Koppert) + TX; Trichoderma harzianum strain TH35 (e.g. Root-Pro from Mycontrol) + TX; Trichoderma harzianum harzianum), strain DB 103 (available as T-GRO® 7456 by Dagutat Biolab) + TX;Trichoderma polysporum, strain IMI 206039 (e.g., Binab TF WP by BINAB Bio-Innovation AB, Sweden) + TX; Trichoderma stromaticum with accession number Ts3550 (e.g., Tricovab by CEPLAC, Brazil) + TX; Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g., SoilGard by Certis, US) + TX; Trichoderma virens strain G-41, formerly known as Gliocladium virens (accession number ATCC 20906) (e.g. ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US) +TX; Trichoderma viride, strain TV1 (e.g. Trianum-P by Koppert) +TX; Trichoderma viride, in particular strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) +TX; Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012), having the accession number CABI CC IMI 392716, Trichoderma gamsii gamsii) (formerly known as T. viride) strain ICC 080, accession number; a mixture of IMI 392151 (e.g., BIO-TAM™ from Isagro USA, Inc. and BIODERMA® from Agrobiosol de Mexico, SA de CV) +TX; Ulocladium oudemansii strain U3 with accession number NM 99 / 06216 (e.g., BOTRY-ZEN® from Botry-Zen Ltd, New Zealand and BOTRYSTOP® from BioWorks, Inc.) +TX; Verticillium albo-atrum (formerly V. dahliae), strain WCS850 with accession number WCS850, deposited at the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® from Tree Care Innovations) +TX; Verticillium chlamydosporium chlamydosporium)+TX; (3) A biological control agent having the effect of improving plant growth and / or plant health selected from the following group: (3.1) Examples of bacteria include Azospirillum brasilense (e.g., VIGOR® from KALO, Inc.) + TX; Azospirillum lipoferum (e.g., VERTEX-IF® from TerraMax, Inc.) + TX; Azorhizobium caulinodans, in particular the strain ZB-SK-5 + TX; Azotobacter chroococcum, in particular the strain H23 + TX; Azotobacter vinelandii, in particular the strain ATCC 12837 + TX; Azotobacter vinelandii and Clostridium pasteurianum. a mixture of Bacillus pasteurianum (available as INVIGORATE® from Agrinos) + TX; Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® from Biofilm Crop Protection) + TX; Bacillus amyloliquefaciens SB3281 (ATCC #PTA-7542, WO 2017 / 205258) + TX; Bacillus amyloliquefaciens TJ1000 (available as QUIKROOTS® from Novozymes) + TX; Bacillus Bacillus amyloliquefaciens, in particular the strain IN937a + TX; Bacillus amyloliquefaciens, in particular the strain FZB42 (e.g. RHIZOVITAL® from ABiTEP, DE) + TX; Bacillus amyloliquefaciens BS27 (accession number NRRL B-5015) + TX;Bacillus cereus family member EE128 (NRRL No. B-50917) + TX; Bacillus cereus family member EE349 (NRRL No. B-50928) + TX; Bacillus cereus, in particular strain BP01 (ATCC 55675, e.g., MEPICHLOR® from Arysta Lifescience, US) + TX; Bacillus firmus, in particular strain CNMC 1-1582 (e.g., VOTIVO® from BASF SE) + TX; Bacillus mycoides BT155 (NRRL No. B-50921) + TX; Bacillus mycoides EE118 (Bacillus mycoides Bacillus mycoides EE118 (NRRL No. B-50918) + TX; Bacillus mycoides EE141 (NRRL No. B-50916) + TX; Bacillus mycoides BT46-3 (NRRL No. B-50922) + TX; Bacillus pumilus, particularly strain QST2808 (Accession No. NRRL No. B-30087) + TX; Bacillus pumilus, particularly strain GB34 (e.g., YIELD SHIELD® from Bayer Crop Science, DE) + TX; Bacillus siamensis, particularly strain KCTC 13613T + TX; Bacillus subtilis subtilis ), specifically strain QST713 / AQ713 (having NRRL accession number B-21661 ; and described in U.S. Pat. No. 6,060,051, available as SERENADE® OPTI or SERENADE® ASO from Bayer CropScience LP, US) +TX; Bacillus subtilis, particularly strain AQ30002 (having accession number NRRL B-50421 and described in U.S. Patent Application Publication No. 13 / 330,576) +TX; Bacillus subtilis, particularly strain AQ30004 (and described in NRRL B-50455 and U.S. Patent Application Publication No. 13 / 330,576) +TX; Bacillus subtilis strain BU1814, (available as TEQUALIS® from BASF SE), Bacillus subtilis rm303 (Biofilm Crop RHIZOMAX® from BioProtein® + TX; Bacillus thuringiensis BT013A (NRRL No. B-50924) (also known as Bacillus thuringiensis 4Q7) + TX; a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation as QUARTZO® (WG), PRESENCE® (WP)) + TX; Bacillus subtilis, particularly strain MBI 600 (e.g., SUBTILEX® from BASF SE) + TX; Bacillus techiensis tequilensis), in particular the strain NII-0943+TX; Bradyrhizobium japonicum (e.g. OPTIMIZE® from Novozymes)+TX;Delftia acidovorans, in particular the strain RAY209 (e.g. BIOBOOST® from Brett Young Seeds) + TX; Mesorhizobium cicer (e.g. NODULATOR from BASF SE) + TX; Lactobacillus sp. (e.g. LACTOPLANT® from LactoPAFI) + TX; Rhizobium leguminosarium biovar viciae (e.g. NODULATOR from BASF SE) + TX; Pseudomonas proradix (e.g. PRORADIX® from Sourcon Padena) + TX; Pseudomonas aeruginosa, in particular the strain PN1 + TX; Rhizobium leguminosarum leguminosarum, in particular bv.viceae strain Z25 (accession number CECT 4585) + TX; Paenibacillus polymyxa, in particular strain AC-1 (e.g. TOPSEED® from Green Biotech Company Ltd.) + TX; Serratia marcescens, in particular strain SRM (accession number MTCC 8708) + TX; Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience) + TX; Thiobacillus sp. (e.g. CROPAID® from Cropaid Ltd UK) + TX; and (3.2) Examples of fungi are: Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, e.g. BioAct from Bayer CropScience Biologics GmbH) +TX; Penicillium bilaii, strain ATCC 22348 (e.g. JumpStart® from Acceleron BioAg), Talaromyces flavus, strain V117b +TX; Trichoderma atroviride strain CNCM 1-1237 (e.g. Esquive® WP from Agrauxine, FR), Trichoderma viride viride), e.g., strain B35 (Pietr et al., 1993, Zesz. Nauk.AR w Szczecinie 161:125-137) +TX; Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, e.g. Sentinel from Agrimm Technologies Limited) +TX; Trichoderma atroviride strain SC1 as described in International Patent Application PCT / Italian Patent Application Publication No. 2008 / 000196 +TX; Trichoderma asperellum strain kd (e.g. T-Gro from Andermatt Biocontrol) +TX; Trichoderma asperellum strain Eco-T (Plant Health Products, ZA), Trichoderma harzianum harzianum strain T-22 (e.g. Trianum-P from Andermatt Biocontrol or Koppert) + TX; Myrothecium verrucaria strain AARC-0255 (e.g. DiTera™ from Valent Biosciences) + TX; Penicillium bilaii strain ATCC ATCC20851 + TX; Pythium oligandrum strain M1 (ATCC38472, e.g. Polyversum from Bioprepraty, CZ) + TX; Trichoderma virens strain GL-21 (e.g. SoilGard™ from Certis, USA) + TX; Verticillium alboatrum albo-atrum (formerly V. dahliae) strain WCS850 (CBS276).92, e.g. Dutch Trig from Tree Care Innovations) +TX; Trichoderma atroviride, in particular strain number V08 / 002387, strain number NMI number V08 / 002388, strain number NMI number V08 / 002389, strain number NMI number V08 / 002390 +TX; Trichoderma harzianum strain ITEM 908, Trichoderma harzianum strain TSTh20 +TX; Trichoderma harzianum strain 1295-22 +TX; Pythium oligandrum strain DV74 +TX; Rhizopogon amylopogon amylopogon (e.g., in Myco-Sol from Helena Chemical Company) + TX; Rhizopogon fulvigleba (e.g., in Myco-Sol from Helena Chemical Company) + TX; Trichoderma virens strain GI-3 + TX; (4) an insecticidally effective biological control agent selected from the following: (4.1) Examples are bacteria such as: Agrobacterium radiobacter strain K84 (Galltrol from AgBiochem Inc.) + TX; Bacillus amyloliquefaciens, in particular the strain PTS-4838 (e.g. AVEO from Valent Biosciences, US) + TX; Bacillus firmus, in particular the strain CNMC1-1582 (e.g. VOTIVO® from BASF SE) + TX; Bacillus mycoides, isolate J. (e.g. BmJ from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.)) + TX; Bacillus sphaericus, in particular the serotype H5a5b strain 2362 (strain ABTS-1743) (e.g. Valent Biosciences, US) + TX; BioSciences, US) + TX; Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372, e.g., XENTARI® from Valent BioSciences) + TX; Bacillus thuringiensis subsp. aizawai, in particular serotype H-7 (e.g., FLORBAC® WG from Valent BioSciences, US) + TX; Bacillus thuringiensis israelensis strain BMP 144 (e.g., AQUABAC® from Becker Microbial Products, IL) + TX; Bacillus thuringiensis subsp. israelensis (Bacillus thuringiensis subsp.israelensis (serotype H-14) strain AM65-52 (accession number ATCC 1276) (e.g., VECTOBAC® from Valent BioSciences, US) +TX; Bacillus thuringiensis subsp. aizawai strain GC-91 +TX; Bacillus thuringiensis var. colmeri (e.g., TIANBAOBTC from Changzhou Jianghai Chemical Factory) +TX; Bacillus thuringiensis var. japonensis strain Buibui +TX; Bacillus thuringiensis subsp. kurstaki strain BMP 123 +TX from Becker Microbial Products, IL; Bacillus thuringiensis subsp. kurstaki strain BMP 123 by Bayer CropScience, Inc., IL, e.g., BARITONE+TX from Bayer CropScience; Bacillus thuringiensis subsp. kurstaki strain HD-1 (e.g., DIPEL® ES from Valent BioSciences, US)+TX; Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global)+TX; Bacillus thuringiensis subsp. kurstaki strain ABTS351 ...kurstaki strain PB 54 + TX; Bacillus thuringiensis subsp. kurstaki strain SA 11 (JAVELIN from Certis, US) + TX; Bacillus thuringiensis subsp. kurstaki strain SA 12 (THURICIDE from Certis, US) + TX; Bacillus thuringiensis subsp. kurstaki strain EG2348 (LEPINOX from Certis, US) + TX; Bacillus thuringiensis subsp. kurstaki strain EG 7841 (CRYMAX from Certis, US) + TX; Bacillus thuringiensis subsp. tenebrionis thuringiensis subsp. tenebrionis strain NB176 (SD-5428, e.g. NOVODOR® FC from BioFa DE) + TX; Brevibacillus laterosporus (LATERAL from Ecolibrium Biologicals) + TX; Burkholderia spp.), in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (Accession No. NRRL B-50319 +TX; WO 2011 / 106491 and WO 2013 / 032693 +TX; e.g., MBI206 TGAI and ZELTO® +TX from Marrone Bio Innovations); Chromobacterium subtsugae, in particular strain PRAA4-1T (MBI-203 +TX; e.g., GRANDEVO® from Marrone Bio Innovations) +TX; Lecanicillium muscarium Ve6 (Lecanicillium muscarium Ve6) (MYCOTAL from Koppert) + TX; Paenibacillus popilliae (formerly Bacillus popilliae) + TX; e.g., MILKY SPORE POWDER™ and MILKY SPORE GRANULAR™ from St. Gabriel Laboratories + TX; Pasteuria nishizawae strain Pn1 (CLARIVA from Syngenta / ChemChina) + TX; Serratia entomophila (e.g., INVADE® by Wrightson Seeds) + TX; Serratia marcescens, particularly strain SRM (accession number MTCC 8708) + TX; Trichoderma asperellum asperellum (TRICHODERMAX from Novozymes) + TX; Wolbachia pipientis ZAP strain (e.g., ZAP MALES® from MosquitoMate) + TX; and (4.2) Examples of fungi are: Beauveria bassiana strain ATCC 74040 (e.g. NATURALIS® from Intrachem Bio Italia) + TX; Beauveria bassiana strain GHA (accession number ATCC 74250, e.g. BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation) + TX; Beauveria bassiana strain ATP02 (accession number DSM24665) + TX; Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain Apopka from SePRO. 97) PREFERAL + TX; Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074) (WO 2017 / 066094 + TX; Pioneer Hi-Bred International) + TX; Metarhizium robertsii 15013-1 (deposited under NRRL accession number 67073) + TX; Metarhizium robertsii 23013-3 (deposited under NRRL accession number 67075) + TX; Paecilomyces lilacinus strain 251 (MELOCON from Certis, US) + TX; Zooftora radicans + TX; (5) A virus selected from the group consisting of: Adoxophyes orana (smaller apple tortrix) granulosis virus (GV) + TX; Cydia pomonella (codling moth) granulosis virus (GV) + TX; Helicoverpa armigera (cotton bollworm) nucleopolyhedrovirus (NPV) + TX; Spodoptera exigua (beet armyworm) mNPV + TX; Spodoptera frugiperda (stalk armyworm) mNPV + TX; Spodoptera littoralis (Egyptian armyworm) NPV + TX; (6) Bacteria and fungi that can be added as an "inoculant" to plants or plant parts or plant tissues and that promote plant growth and plant health due to their specific properties, selected from the following: Agrobacterium spp. + TX; Azorhizobium caulinodans + TX; Azospirillum spp. + TX; Azotobacter spp. + TX; Bradyrhizobium spp. + TX; Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia) + TX; Gigaspora spp. spp.) or Gigaspora monosporum + TX; Glomus spp. + TX; Laccaria spp. + TX; Lactobacillus buchneri + TX; Paraglomus spp. + TX; Pisolithus tinctorus + TX; Pseudomonas spp. + TX; Rhizobium spp., especially Rhizobium trifolii + TX; Rhizopogon spp. + TX; Scleroderma spp. + TX; Suillus spp.) + TX;Streptomyces spp.) + TX; (7) Plant extracts and products formed by microorganisms containing proteins and secondary metabolites that can be used as biological control agents, selected from the following: garlic (Allium sativum) (NEMGUARD from Eco-Spray) + TX; BRALIC from ADAMA) + TX; Armour-Zen + TX; Artemisia absinthium + TX; azadirachtin (e.g. AZATIN XL from Certis, US) + TX; Biokeeper WP + TX; Brassicaceae extracts, in particular rapeseed powder or mustard powder + TX; Cassia nigricans + TX; Celastrus angulatus + TX; Chenopodium anthelminticum + TX; chitin + TX; Dryopteris filix-mas) + TX; Horsetail (Equisetum arvense) + TX; Fortune Aza + TX; Fungastop + TX; Heads Up (Quinoa (Chenopodium quinoa) saponin extract) + TX; PROBLAD (Natural Blad Polypeptide from Lupine Seed), Certis EU + TX; FRACTURE (Natural Blad Polypeptide from Lupine Seed), FMC + TX; Calyx / Pyrethrin + TX; Quassia amara + TX; Quercus (Quercus spp.) + TX; Quillaja (Quillaja) extract (QL AGRI 35 from BASF) + TX; Giant Knotweed (Reynoutria sachalinensis) extract (REGALLIA / REGALIA from Marrone Bio) MAXX) + TX; "Requiem™ Insecticide" + TX; Rotenone + TX; Ryania / Ryanodine + TX; Comfrey (Symphytum officinale) + TX; Tansy (Tanacetum vulgare) + TX; Thymol + TX; Thymol mixed with geraniol (CEDROZ from Eden Research) + TX;Thymol mixed with geraniol and eugenol (MEVALONE from Eden Research) +TX; Triact 70 +TX; TriCon +TX; nasturtium (Tropaeulum majus) +TX; Melaleuca alternifolia extract (TIMOREX GOLD from STK) +TX; nettle (Urtica dioica) +TX; veratrine +TX; and mistletoe (Viscum album) +TX; and Safeners such as benoxacor + TX, cloquintocet (including cloquintocet-mexyl) + TX, cyprosulfamide + TX, dichlormid + TX, fenchlorazole (including fenchlorazole-ethyl) + TX, fenclorim + TX, fluxofenim + TX, furilazole + TX, isoxadifen (including isoxadifen-ethyl) + TX, mefenpyr (including mefenpyr-diethyl) + TX, metcamifen + TX and oxabetrinil + TX.

[0453] The reference numbers in square brackets after the active ingredient, such as [3878-19-1], refer to the Chemical Abstracts Registration Number. The above-mentioned compounds are known. When the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: CDS Tomlin; The British Crop Protection Council], they are listed therein under the section number shown in parentheses above for the specific compound; for example, the compound "abamectin" is listed under section number (1). When "[CCN]" is added to a specific compound above, the corresponding compound is included in the "Compendium of Pesticide Common Names," which is accessible on the Internet [A. Wood; Compendium of Pesticide Common Names, (Copyright) 1995-2004]; for example, the compound "acetoprole" is listed at the Internet address: http: / / www.alanwood.net / pesticides / acetoprole.html.

[0454] Most of the active ingredients mentioned above are referred to above by so-called "common names", and the relevant "ISO common names" or another "common name" is used in individual cases. If the designation is not a "common name", the nature of the designation used instead is indicated in parentheses for the particular compound; in that case, the IUPAC name, IUPAC / Chemical Abstracts name, "chemical name", "trivial name", "compound name" or "development code" is used, or if neither one of these designations nor a "common name" is used, an "alternative name" is used. "CAS Registry Number" means the Chemical Abstracts Registry Number.

[0455] The active ingredient mixture of a compound of formula I selected from Tables A-1 to A-36, Tables B-1 to B-36, Tables C-1 to C-36, Tables D-1 to D-36 and Table P with the above active ingredient is preferably a mixture of a compound selected from Tables A-1 to A-36, Tables B-1 to B-36, Tables C-1 to C-36, Tables D-1 to D-36 and Table P with the above active ingredient in a mixing ratio of preferably 100:1 to 1:6000, in particular 50:1 to 1:50, more in particular 20:1 to 1:20, even more in particular 10:1 to 1:10, very in particular 5:1 and 1:5 (a ratio of 2:1 to 1:2 is particularly preferred, and a ratio of 4:1 to 2:1 is likewise preferred), especially 1:1 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. These mixing ratios are by weight.

[0456] The mixture can be used in a method of controlling pests, the method comprising the step of applying a composition comprising the mixture to the pest or its environment, excluding methods of treatment of the human or animal body by surgery or therapy and diagnostic methods performed on the human or animal body.

[0457] Mixtures comprising a compound of formula I selected from Tables A-1 to A-36, Tables B-1 to B-36, Tables C-1 to C-36, Tables D-1 to D-36, and Table P and one or more of the active ingredients described above can be applied, for example, in a single ready-mix form, as a combined spray mixture made up of separate formulations of a single active ingredient, such as a "tank mix," and in combination with a single active ingredient when applied sequentially, i.e., within a fairly short period of time, such as a few hours or days. The order of application of a compound of formula I selected from Tables A-1 to A-36, Tables B-1 to B-36, Tables C-1 to C-36, Tables D-1 to D-36, and Table P and the active ingredients described above is not critical to the practice of the present invention.

[0458] The compositions according to the invention may also comprise further solid or liquid auxiliaries, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example epoxidized palm oil, rapeseed oil or soybean oil), antifoaming agents, for example silicone oils, preservatives, viscosity regulators, binders and / or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0459] The compositions according to the invention can be prepared in a manner known per se in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid active ingredient, and in the presence of at least one auxiliary, for example by intimately mixing the active ingredient with one or more auxiliaries and / or grinding it. These methods for preparing the compositions and the use of compound I for preparing these compositions are also the subject of the present invention.

[0460] The application methods for the compositions, i.e., spraying, atomizing, dusting, brushing, dusting, spreading, or pouring (which should be selected according to the intended purpose in the prevailing situation), are other subjects of the present invention. Typical concentration rates are 0.1 to 1000 ppm, preferably 0.1 to 500 ppm, of active ingredient. The application rate per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g / ha, preferably 10 to 600 g / ha.

[0461] The preferred method of application in the field of crop protection is application to the foliage of plants (foliar application), and the frequency and rate of application can be selected according to the risk of infestation by the relevant pest. Alternatively, the active ingredient can reach the plant via the root system (systemic action) by irrigating the plant habitat with a liquid composition or by introducing the active ingredient in solid form into the plant habitat, for example, the soil, for example in the form of granules (soil application). In the case of paddy rice plants, such granules can be metered into the paddy field.

[0462] The compounds of the present invention and compositions thereof are also suitable for protecting plant propagation material, such as seeds or seedlings of fruits, tubers, or grains, from the above-mentioned types of pests. The propagation material can be treated with the compounds before planting, for example, seeds can be treated before sowing. Alternatively, the compounds can be applied to the seed kernels by immersing them in a liquid composition or by applying a layer of a solid composition (coating). When the propagation material is planted at the application site, the compositions can also be applied between the furrows, for example, during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the present invention. Typical treatment rates depend on the plant and the pests / fungi to be controlled and are generally 1 to 200 grams per 100 kg of seeds, preferably 5 to 150 grams per 100 kg of seeds (e.g., 10 to 100 grams per 100 kg of seeds).

[0463] The term seed encompasses all types of seeds and plant propagules, including but not limited to true seeds, seed pieces, suckers, kernels, bulbs, fruits, tubers, grains, rhizomes, cuttings, cuttings, etc., and in preferred embodiments refers to true seeds.

[0464] The present invention also includes seeds coated or treated with or containing a compound of formula (I). The term "coated or treated with and / or containing" generally indicates that the active ingredient is most often on the surface of the seed upon application, but that depending on the application method, some of the ingredient may penetrate to varying degrees into the seed material. When the seed product is (re)planted, it may absorb the active ingredient. In an embodiment, the present invention provides a plant propagation material having a compound of formula (I) attached thereto. Furthermore, the present invention provides a composition comprising plant propagation material treated with a compound of formula (I).

[0465] Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. The seed treatment application of the compound of formula (I) can be carried out by any known method, such as spraying, or by dusting the seeds before sowing or during sowing / planting of the seeds.

[0466] Biological Examples: The following examples illustrate the invention. Certain compounds of the invention can be distinguished from known compounds by their high efficacy at low application rates, which can be verified by those skilled in the art using the experimental procedures outlined in the examples, using lower application rates, such as 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm, if necessary.

[0467] Example B1: Activity against Chilo suppressalis (rice stem borer) Twenty-four-well microtiter plates containing artificial diet were treated by pipette with test solutions prepared from a 10,000 ppm DMSO stock solution. After drying, the plates were infested with L2 larvae (6-8 per well). Samples were evaluated for mortality, antifeedant effect, and growth inhibition compared to untreated samples 6 days after infestation. Control of rice stem borer (Chilo suppressalis) by the test sample was indicated if at least one of the categories of mortality, antifeedant effect, and growth inhibition was higher than that of untreated samples.

[0468] The following compounds provided at least 80% control at an application rate of 200 ppm: P2, P4, P5, P7, P8, P9, P10, P11, P13, P14, P15.

[0469] Example B2: Activity against Diabrotica balteata (corn rootworm) Corn sprouts placed on agar layers in 24-well microtiter plates were treated by spraying with test solutions prepared from a 10,000 ppm DMSO stock solution. After drying, the plates were infested with L2 larvae (6-10 per well). Samples were evaluated for mortality and growth inhibition four days after infestation compared to untreated samples.

[0470] The following compounds produced at least 80% efficacy in at least one of two categories (mortality or growth inhibition) at an application rate of 200 ppm: P2, P3, P4, P5, P7, P9, P10, P11, P13, P14, P15.

[0471] Example B3: Activity against Euschistus heros (Neotropical Brown Stink Bug) Soybean leaves on agar in 24-well microtiter plates were sprayed with test solutions prepared from a 10,000 ppm DMSO stock solution. After drying, the leaves were infested with N2 nymphs. Samples were evaluated for mortality and growth inhibition 5 days after infestation compared to untreated samples.

[0472] The following compounds produced at least 80% efficacy in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P2, P3, P4, P5, P7, P11, P13, P14, P15. 【04...

Claims

1. Compounds of formula (I) 【Chemistry 1】 (In the formula, R 2 is C 1 ~C 6 Haloalkyl, C 1 ~C 4 Haloalkylsulfanyl, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl or C 1 ~C 6 haloalkoxy; G is CH or N; X 1 is O, S or NR 6 where R 6 is C 1 ~C 4 is alkyl; R 7 is hydrogen, C 1 ~C 4 is alkyl or halogen; Q is a compound of formula Qa and Qb 【Chemistry 2】 where the arrow indicates the point of attachment to the bicyclic ring; and A represents CH or N; X is S, SO, SO 2 and R 1 is C 1 ~C 4 Alkyl or C 3 ~C 6 Cycloalkyl-C 1 ~C 4 is alkyl; Q 1 is hydrogen, halogen, C 1 ~C 6 Haloalkyl, C 3 ~C 6 Cycloalkyl, monosubstituted with cyano 3 ~C 6 Cycloalkyl, C 1 ~C 6 Cyanoalkyl, C 1 ~C 6 Cyanoalkoxy, C 1 ~C 6 haloalkoxy, —N(R 4 ) 2 , -N(R 4 ) COR 5 or 2-pyridyloxy; or Q 1 is a 5- to 6-membered aromatic or heteroaromatic ring system bonded via a ring carbon atom to the ring containing the substituent A, the ring system being unsubstituted or substituted with halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl and C 1 ~C 4 alkylsulfonyl; and the ring system may contain 1, 2, or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, wherein the ring system may contain no more than one ring oxygen atom and no more than one ring sulfur atom; or Q 1 is a 5-membered aromatic heterocyclic ring system bonded to the ring containing the substituent A via a ring nitrogen atom, the ring system being unsubstituted or substituted with halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl and C 1 ~C 4 alkylsulfonyl; and said ring system contains 1, 2, or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, wherein said ring system contains at least one ring nitrogen atom and may contain no more than one ring oxygen atom and may contain no more than one ring sulfur atom; R 3 is hydrogen or C 1 ~C 4 is alkyl; Each R 4 are independently hydrogen, C 1 ~C 4 Alkyl or C 3 ~C 6 is cycloalkyl; and R 5 is C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl or C 3 ~C 6 cycloalkyl) is a group selected from the group consisting of or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I.

2. Compound of Formula I-1 【Transformation 3】 (In the formula, R 2 , G, X 1 , R 6 , R 7 , A, X, R 1 , Q 1 , R 3 , R 4 and R 5 is as defined for formula I in claim 1), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of the compound of formula I-1.

3. R 2 is -CF 3 , -OCF 3 or -OCHF 2 and G is CH or N; X 1 is O, S or NCH 3 and R 7 is hydrogen or methyl; A is N or CH; X is S or SO 2 and R 1 is ethyl or cyclopropylmethyl; Q 1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, —N(CH 3 ) COCH 3 , -N(CH 3 ) COCH 2 CH 3 , -N(CH 3 )CO(cyclopropyl) or 2-pyridyloxy; and R 3 The compound of formula I-1 according to claim 2, wherein is hydrogen or methyl.

4. R 2 is -CF 3 , -OCF 3 or -OCHF 2 and G is CH; X 1 is O; R 7 is hydrogen; A is N; X is SO 2 and R 1 is ethyl; Q 1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, —N(CH 3 ) COCH 3 , -N(CH 3 ) COCH 2 CH 3 , -N(CH 3 )CO(cyclopropyl) or 2-pyridyloxy; and R 3 The compound of formula I-1 according to claim 2, wherein is hydrogen.

5. R 2 is -CF 3 , -OCF 3 or -OCHF 2 and G is CH or N; X 1 is O, S or NCH 3 and R 7 is hydrogen or methyl; A is N or CH; X is S or SO 2 and R 1 is ethyl or cyclopropylmethyl; Q 1 is N-linked triazolyl, C-linked pyrimidinyl, or N-linked pyrazolyl, which may be monosubstituted with chloro, cyano, or trifluoromethyl; and R 3 The compound of formula I-1 according to claim 2, wherein is hydrogen or methyl.

6. R 2 is -CF 3 , -OCF 3 or -OCHF 2 and G is CH; X 1 is O; R 7 is hydrogen; A is N; X is SO 2 and R 1 is ethyl; Q 1 is pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl; and R 3 The compound of formula I-1 according to claim 2, wherein is hydrogen.

7. Compound of Formula I-2 【Chemistry 4】 (In the formula, R 2 , G, X 1 , R 6 , R 7 , A, X, R 1 , Q 1 , R 3 , R 4 and R 5 is as defined for formula I in claim 1), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-2.

8. R 2 is -CF 3 , -OCF 3 or -OCHF 2 and G is CH or N; X 1 is O, S or NCH 3 and R 7 is hydrogen or methyl; A is N or CH; X is S or SO 2 and R 1 is ethyl or cyclopropylmethyl; Q 1 is hydrogen, cyclopropyl, -NH(CH 3 ), -N(CH 3 ) COCH 3 , -N(CH 3 ) COCH 2 CH 3 or -N(CH 3 )CO(cyclopropyl); and R 3 The compound of formula I-2 according to claim 7, wherein is hydrogen or methyl.

9. R 2 is -CF 3 , -OCF 3 or -OCHF 2 and G is CH; X 1 is O; R 7 is hydrogen; A is N; X is SO 2 and R 1 is ethyl; Q 1 is hydrogen, cyclopropyl, -NH(CH 3 ), -N(CH 3 ) COCH 3 , -N(CH 3 ) COCH 2 CH 3 or -N(CH 3 )CO(cyclopropyl); and R 3 The compound of formula I-2 according to claim 7, wherein is hydrogen.

10. R 2 is -CF 3 , -OCF 3 or -OCHF 2 and G is CH or N; X 1 is O, S or NCH 3 and R 7 is hydrogen or methyl; A is N or CH; X is S or SO 2 and R 1 is ethyl or cyclopropylmethyl; Q 1 is N-linked triazolyl or C-linked pyrimidinyl; and R 3 The compound of formula I-2 according to claim 7, wherein is hydrogen or methyl.

11. R 2 is -CF 3 , -OCF 3 or -OCHF 2 and G is CH; X 1 is O; R 7 is hydrogen; A is N; X is SO 2 and R 1 is ethyl; Q 1 is 1,2,4-triazol-1-yl or pyrimidin-2-yl; and R 3 The compound of formula I-2 according to claim 7, wherein is hydrogen.

12. Compound of Formula I-3 【Transformation 5】 (In the formula, R 2 is C 1 ~C 2 Fluoroalkyl or C 1 ~C 2 fluoroalkoxy, preferably R 2 is -CF 3 , -OCF 3 or -OCHF 2 and G is CH or N; X 1 is O, S or NCH 3 and R 7 is hydrogen or methyl; Q' is a group of the formula Qa1 and Qb1 【Transformation 6】 where the arrow indicates the point of attachment to the bicyclic ring; and Q 1 is an N-linked pyrazolyl which may be monosubstituted with hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, 2-pyridyloxy, chloro, cyano, or trifluoromethyl; or Q 1 is an N-linked triazolyl, a C-linked pyrimidinyl or —N(R 4 ) COR 5 where R 4 is hydrogen or methyl, and R 5 is methyl, ethyl or cyclopropyl) or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of the compound of formula I-3.

13. Q 1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, —N(CH 3 ) COCH 3 , -N(CH 3 ) COCH 2 CH 3 , -N(CH 3 13. The compound of formula I-3 according to claim 12, wherein the compound is 2-pyridyloxy, 3-chloro-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

14. Q 1 The compound of formula I-3 according to claim 12, wherein is hydrogen, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, N-linked triazolyl or C-linked pyrimidinyl.

15. Q 1 Compounds of formula I-3 according to claim 12, wherein is hydrogen, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

16. G is CH; X 1 is O; and R 7 Compounds of formula I-3 according to claim 12, wherein is hydrogen or methyl, preferably hydrogen.

17. G is N; X 1 is O; and R 7 Compounds of formula I-3 according to claim 12, wherein is hydrogen or methyl, preferably hydrogen.

18. 3-(3-ethylsulfanyl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (compound P1); 3-(3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (compound P2); 1-[5-ethylsulfanyl-6-[4-oxo-7-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropanecarbonitrile (compound P3); 1-[5-ethylsulfonyl-6-[4-oxo-7-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropane-carbonitrile (compound P4); 2-[5-ethylsulfonyl-6-[4-oxo-7-(trifluoromethyl)chromen-3-yl]-3-pyridyl]-2-methyl-propane-nitrile (compound P5); 2-[[5-ethylsulfonyl-6-[4-oxo-7-(trifluoromethyl)chromen-3-yl]-3-pyridyl]oxy]-2-methyl-propanenitrile (compound P6) 1-[5-ethylsulfonyl-6-[2-methyl-4-oxo-7-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropane-carbonitrile (compound P7); 3-(5-bromo-3-ethylsulfonyl-2-pyridyl)-2-methyl-7-(trifluoromethyl)chromen-4-one (compound P8); 3-(5-bromo-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)-chromen-4-one (compound P9); 3-(6-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (compound P10); 3-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (compound P11); 1-[5-ethylsulfonyl-6-[4-oxo-7-(trifluoromethyl)pyrano[2,3-b]pyridin-3-yl]-3-pyridyl]-cyclopropanecarbonitrile (compound P12); 1-[6-[7-(difluoromethoxy)-4-oxo-chromen-3-yl]-5-ethylsulfonyl-3-pyridyl]-cyclopropanecarbonitrile (compound P13); 1-[5-ethylsulfonyl-6-[1-methyl-4-oxo-7-(trifluoromethyl)-3-quinolyl]-3-pyridyl]-cyclopropanecarbonitrile (compound P14); 1-[5-ethylsulfonyl-6-[4-oxo-7-(trifluoromethoxy)chromen-3-yl]-3-pyridyl]-cyclopropane-carbonitrile (compound P15); 3-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P16); 3-[5-(difluoromethoxy)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P17); 3-(3-ethylsulfonyl-5-pyrimidin-2-yl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (compound P18); 3-[3-ethylsulfonyl-5-(2,4,5-trifluorophenyl)-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P19); 3-[3-ethylsulfonyl-5-[4-(trifluoromethyl)phenyl]-2-pyridyl]-7-(trifluoromethyl)-chromen-4-one (compound P20); 3-[5-(4-chloro-2,6-dimethyl-phenyl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)-chromen-4-one (compound P21); 3-[5-(4-chlorophenyl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P22); 3-[5-(6-chloro-3-pyridyl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P23); 3-[3-ethylsulfonyl-5-(5-fluoro-2-thienyl)-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P24); 3-[5-(3-chloro-4-fluoro-phenyl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P25); 3-[5-(1-ethyl-3,5-dimethyl-pyrazol-4-yl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)-chromen-4-one (compound P26); 3-[3-ethylsulfonyl-5-(3-pyridyl)-2-pyridyl]-7-(trifluoromethyl)-chromen-4-one (compound P27); 3-(3-ethylsulfonyl-5-pyrimidin-5-yl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (compound P28); 3-[5-(1,3-dimethylpyrazol-4-yl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P29); 3-[3-ethylsulfonyl-5-(6-fluoro-3-pyridyl)-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P30); 3-[5-(1,4-dimethylpyrazol-3-yl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P31); 3-[5-(5-chloro-2-thienyl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P32); 3-[3-ethylsulfonyl-5-(1-isopropylpyrazol-4-yl)-2-pyridyl]-7-(trifluoromethyl)-chromen-4-one (compound P33); 3-[3-ethylsulfonyl-5-(2-methylpyrimidin-5-yl)-2-pyridyl]-7-(trifluoromethyl)-chromen-4-one (compound P34); 3-[3-ethylsulfonyl-5-(3-fluorophenyl)-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P35); 3-[5-(1,5-dimethylpyrazol-4-yl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P36); 3-[3-ethylsulfonyl-5-(3,4,5-trifluorophenyl)-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P37); 3-[3-ethylsulfonyl-5-[4-(trifluoromethyl)-2-thienyl]-2-pyridyl]-7-(trifluoromethyl)-chromen-4-one (compound P38); 3-[3-ethylsulfonyl-5-[5-(trifluoromethyl)-3-thienyl]-2-pyridyl]-7-(trifluoromethyl)-chromen-4-one (compound P39); 3-(3-ethylsulfonyl-5-isoxazol-4-yl-2-pyridyl)-7-(trifluoromethyl)-chromen-4-one (compound P40); 3-[3-ethylsulfonyl-5-(1-methylpyrrol-3-yl)-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P41); 3-[3-ethylsulfonyl-5-[6-(trifluoromethoxy)-3-pyridyl]-2-pyridyl]-7-(trifluoromethyl)-chromen-4-one (compound P42); 3-[5-(3,5-dichloro-4-fluoro-phenyl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)-chromen-4-one (compound P43); 3-[5-(3-chloro-5-fluoro-phenyl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P44); 3-[5-(3,5-dichlorophenyl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P45); 3-[5-(1-ethylpyrazol-3-yl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P46); 3-(3-ethylsulfonyl-5-pyrazin-2-yl-2-pyridyl)-7-(trifluoromethyl)chromen-4-one (compound P47); 3-[5-(4-chloro-2-fluoro-phenyl)-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)chromen-4-one (compound P48), 2. The compound of formula I according to claim 1, selected from the group consisting of:

19. 19. A composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) according to any one of claims 1 to 18, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, and optionally an auxiliary or diluent.

20. 20. A method for combating and controlling insects, acaridae, nematodes or molluscs, the method comprising the step of applying to the pest, the pest's habitat or plants susceptible to attack by the pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) according to any one of claims 1 to 18 or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

21. A method for the extermination and control of insects, mites, nematodes or molluscs, comprising the step of applying to the pest, the pest's habitat or plants susceptible to attack by the pest an insecticidally, acaricidally, nematicidally or molluscicidal amount of the composition of claim 19.

22. 20. A method for protecting plant propagation material from attack by insects, mites, nematodes or mollusks, comprising treating the propagation material or the location where the propagation material is planted with the composition of claim 19.

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