Pesticidal cyclic amine compounds

Abstract

Compounds of formula (I) - wherein the substituents are as defined in claim 1 - and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds can be used as insecticides. (I).

Description

[0001] This invention relates to piperazine-pyridyl carbonyl compounds with pest-killing activity (particularly insecticidal activity), methods for their preparation, compositions comprising those compounds, and their use for controlling animal pests (including arthropods and particularly insects or representatives of mites).

[0002] WO 2015032280, WO 2019039429, JP2019077618, WO 2021053161, WO 2022070023 and WO 2022207462 describe certain piperazine-pyridinyl carbonyl compounds for the control of harmful organisms that damage plants.

[0003] Another novel piperazine-pyridinyl carbonyl compound that kills pests has now been discovered.

[0004] Therefore, in a first aspect, the present invention relates to compounds having formula (I).

[0005] (I)

[0006] in

[0007] R 1 It is ethyl;

[0008] R 2 It is H or methyl;

[0009] R 3 It is a C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, or C3-C4-halocycloalkyl;

[0010] R 4 It is a phenyl group, substituent with 1 to 3 R groups. 5 Substituted phenyl, heteroaryl (which is a 5- or 6-membered monocyclic or a 9- or 10-membered bicyclic), or substituted with 1 to 3 R groups 6 Substituted heteroaryl groups (which are 5 or 6-membered monocyclic or 9 or 10-membered bicyclic).

[0011] R 5 and R 6 The components are independently selected from halogens, C1-C3-haloalkyl and C1-C3-haloalkoxy; and if the two C1-C3-haloalkoxy groups are substituted on adjacent atoms on the phenyl ring, they can form a 5- or 6-membered ring (e.g., –OC1-C2-haloalkylO-) together with the carbon of the phenyl ring.

[0012] Or, chemically acceptable salts, stereoisomers, enantiomers, tautomers, and N-oxides of compounds having formula (I).

[0013] Compounds having at least one basic center and having formula (I) can form, for example, acid addition salts with: strong inorganic acids (such as mineral acids, such as perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid, or hydrohalic acid), strong organic carboxylic acids (such as unsubstituted or, for example, halogenated C1-C4 alkylcarboxylic acids, such as acetic acid, saturated or unsaturated dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, or phthalic acid, such as hydroxycarboxylic acids, such as ascorbic acid, lactic acid, malic acid, tartaric acid, or citric acid, or such as benzoic acid), or organic sulfonic acids (such as unsubstituted or, for example, halogenated C1-C4 alkylsulfonic acids or arylsulfonic acids, such as methanesulfonic acid or p-toluenesulfonic acid). A compound having at least one acidic group of formula (I) may, for example, form a salt with a base, such as a mineral salt, like an alkali metal or alkaline earth metal salt, such as a sodium salt, potassium salt or magnesium salt; or form a salt with ammonia or an organic amine (such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-alkylamines, such as ethylamine, diethylamine, triethylamine or dimethylpropylamine, or mono-, di- or tri-hydroxyalkylamines, such as monoethanolamine, diethanolamine or triethanolamine).

[0014] In each case, the compound having formula (I) according to the invention is in a free form, in an oxidized form (such as an N-oxide) or in a salt form (e.g., in the form of an agronomically available salt).

[0015] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing heteroaromatic compounds. They are described, for example, in A. Albini and S. Pietra’s book “Heterocyclic N-oxides”, CRC Press, Boca Raton, 1991.

[0016] The compounds of formula (I) according to the invention also include hydrates that may form during salt formation.

[0017] As used in this article, the term "C1-C" n "-alkyl" refers to a saturated straight-chain or branched hydrocarbon group having 1 to n carbon atoms attached to any one of these carbon atoms, such as any one of the groups methyl, ethyl or n-propyl.

[0018] As used in this article, the term "C3-C" n "-Cycloalkyl" refers to 3- or n-membered cycloalkyl groups, such as cyclopropane and cyclobutane.

[0019] Halogens are typically fluorine, chlorine, bromine, or iodine. This also applies accordingly to halogens combined with other meanings, such as alkyl halogens.

[0020] As used in this article, the term "C1-C" n"-Halogenated alkyl" refers to a straight-chain or branched saturated alkyl group (as mentioned above) having 1 to n carbon atoms attached to any one of these 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., any one of the following: chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-fluoroethyl -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, or 1-(bromomethyl)-2-bromoethyl. Accordingly, the term "C1-C2 fluoroalkyl" will refer to a C1-C2 alkyl group having 1, 2, 3, 4, or 5 fluorine atoms, such as any one of the following groups: difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, or pentafluoroethyl. Similarly, as used herein, the term "C3-C n "-Halocycloalkyl" refers to a C3-C structure that is substituted with one or more halogen atoms that may be the same or different. n -Cycloalkyl. Similarly, as used herein, the term "C1-C" refers to... n "-Haloalkoxy" refers to a C1-C group that is substituted by one or more halogen atoms that may be the same or different. n -alkoxy group, and if both C1-C n When a haloalkoxy group is substituted on an adjacent atom of the phenyl ring, it can form a 5- or 6-membered ring with the carbon atom of the phenyl ring (e.g., –OC1-C2-haloalkylO-; or -OC). 1-2 (haloalkyldiyl-O-substituent).

[0021] As used herein, the term "5- or 6-membered monocyclic heteroaryl" refers to a 5- or 6-membered aromatic ring in which 1 to 3 carbon atoms are independently replaced by nitrogen, sulfur, or oxygen. Examples are pyridinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyrroleyl, pyrazolyl, imidazolyl, triazolyl (e.g., 1,2,4-triazolyl), furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, and thiadiazolyl.

[0022] As used herein, the term "9- or 10-membered bicyclic heteroaryl" refers to a 9- or 10-membered aromatic ring consisting of two rings, wherein one to three carbon atoms in the ring are independently replaced by nitrogen, sulfur, or oxygen (these heteroatoms may be in one ring or distributed across both rings). Examples are purine, quinolinyl, cenolinyl, quinoxalinyl, indole, indazole, benzimidazolyl, benzothiophene, and benzothiazolyl.

[0023] As used herein, the term “control” refers to reducing the number of pests, eliminating pests, and / or preventing further pest damage, thereby reducing damage to plants or plant-derived products.

[0024] As used herein, the term "pest" refers to insects and mollusks present in the storage of agricultural, horticultural, forestry, and plant-derived products (such as fruits, grains, and timber); as well as pests associated with damage to man-made structures. The term "pest" encompasses all stages of the pest life cycle.

[0025] As used herein, the term "effective amount" refers to the amount of a compound or its salt that provides the desired effect when applied in a single or multiple applications.

[0026] The effective amount is readily determined by those skilled in the art using known techniques and by observing results obtained under similar conditions. In determining the effective amount, numerous factors are considered, including but not limited to: the type of plant or derivative to be applied; the pest to be controlled and its life cycle; the specific compound applied; the type of application; and other relevant circumstances.

[0027] Embodiments of the present invention are provided, as listed below.

[0028] In embodiments of each aspect of the invention, R 2 yes

[0029] A. Hydrogen, or

[0030] B. Methyl.

[0031] In embodiments of each aspect of the invention, R 3 yes

[0032] A. C1-C3-alkyl, C1-C3-haloalkyl, or C3-C4-cycloalkyl, or

[0033] B. Methyl, ethyl, difluoromethyl, trifluoromethyl, or cyclopropyl; or

[0034] C. Methyl, difluoromethyl, trifluoromethyl, or cyclopropyl; or

[0035] D. Difluoromethyl or trifluoromethyl; or

[0036] E. Difluoromethyl.

[0037] In embodiments of each aspect of the invention, R 4 yes

[0038] A. Phenyl, with 1 to 3 substituents R 5 Substituted phenyl, 5- or 6-membered monocyclic heteroaryl, or substituted with 1 to 3 R groups 6 Substituted 5- or 6-membered monocyclic heteroaryl groups; or

[0039] B. 5- or 6-membered monocyclic heteroaryl group, or substituented by 1 to 3 R groups 6 Substituted 5- or 6-membered monocyclic heteroaryl groups; or

[0040] C. Substituted with 1 to 3 R groups 6 Substituted 6-membered monocyclic heteroaryl; or

[0041] D. Substituted with 1 to 3 R groups 6 Substituted pyridine; or

[0042] E. Pyridine substituted with 1 to 3 halogens; or

[0043] F. Substituted by 1 R group 6 Substituted pyridine; or

[0044] G. Pyridine substituted with one halogen; or

[0045] H. pyridine substituted with bromine; or

[0046] I. Substituted with 1 to 3 R groups 5 Substituted phenyl; or

[0047] J. A phenyl group substituted with one to three independent substituents selected from halogens, C1-C3-haloalkyl groups, and C1-C3-haloalkoxy groups; and if the two C1-C3-haloalkoxy groups are substituted on adjacent atoms of the phenyl ring, they can form a 5- or 6-membered ring (e.g., -OC) together with the carbon atoms of the phenyl ring. 1-2 (haloalkyldiyl-O-substituent); or

[0048] K. A phenyl group substituted with one or two independent substituents selected from halogens, C1-C3-haloalkyl groups, and C1-C3-haloalkoxy groups; and if the two C1-C3-haloalkoxy groups are substituted on adjacent atoms of the phenyl ring, they can form a 5- or 6-membered ring (e.g., -OC) together with the carbon atoms of the phenyl ring. 1-2 (haloalkyldiyl-O-substituent); or

[0049] L. A phenyl group substituted with 1-2 independent substituents selected from halogens, difluoromethyl, trifluoromethyl, difluoromethoxy, and trifluoromethoxy; and if the two fluoroalkoxy groups are substituted on adjacent atoms of the phenyl ring, they can form a 5- or 6-membered ring (e.g., -OC) together with the carbon atom of the phenyl ring. 1-2 (haloalkyldiyl-O-substituent); or

[0050] M. A phenyl group substituted with one or two substituents independently selected from chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, and -OCF2-O- groups forming a 5-membered ring with the carbon atom of the phenyl ring (substituted on adjacent carbon atoms of the phenyl ring); or

[0051] N. A phenyl group that is substituted on an adjacent carbon by a -OCF2-O- group that forms a 5-membered ring together with the carbon of the phenyl ring.

[0052] In embodiments of each aspect of the invention, R 5 Selected independently

[0053] A. Halogens, C1-C3-haloalkyl groups, C1-C3-haloalkoxy groups, and -OCF2-O- (substituted later on adjacent carbons, the group forming a 5-membered ring with the carbon of the phenyl ring); or

[0054] B. Fluorine, chlorine, bromine, iodine, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, and -OCF2-O- (substituted later on adjacent carbons, the group forming a 5-membered ring with the carbon of the phenyl ring), or

[0055] C. Fluorine, chlorine, bromine, iodine, trifluoromethyl, and -OCF2-O- (substituted later on adjacent carbons, the group forming a 5-membered ring with the carbon of the phenyl ring), or

[0056] D. Fluorine, chlorine, bromine, iodine, and -OCF2-O- (substituted later on adjacent carbons, the group forming a 5-membered ring with the carbon of the phenyl ring), or

[0057] E. -OCF2-O- (substitution on adjacent carbons, the group together with the carbon of the phenyl ring forms a 5-membered ring).

[0058] In embodiments of each aspect of the invention, R 6 Selected independently

[0059] A. Halogens, C1-C3-haloalkyl groups, and C1-C3-haloalkoxy groups; or

[0060] B. Fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl, trifluoromethoxy, and difluoromethoxy; or

[0061] C. Fluorine, chlorine, bromine, trifluoromethyl, and difluoromethyl; or

[0062] D. Bromine.

[0063] Therefore, the present invention makes it possible to obtain substituents R having all combinations / permutations as defined above. 1 R 2 R 3 and R 4 Compounds having formula (I). Therefore, for example, it is possible to obtain compounds having formula (I), wherein R... 1 It is ethyl; R 2 It is Implementation Example B (i.e., R) 2 (It is methyl); R 3 This is Example A (i.e., R) 3 It is a C1-C3-alkyl, C1-C3-haloalkyl, or C3-C4-cycloalkyl); and R 4 This is Example I (i.e., R) 4 It is substituent by 1 to 3 R groups 5 Substituted phenyl; wherein R 5 It is Implementation D (i.e., R) 5 Independently selected from fluorine, chlorine, bromine, iodine and -OCF2-O-).

[0064] In embodiments of each aspect of the invention, the compound having formula (I) has as R 1 Ethyl group, as R 2 The hydrogen or methyl group, as R 3 Selected from methyl, difluoromethyl, trifluoromethyl, or cyclopropyl; and as R 4 R with 1 to 3 substituents 5 Substituted phenyl, wherein R 5 It is independently selected from halogens, C1-C3-haloalkyl, C1-C3-haloalkoxy and -OCF2-O-.

[0065] In embodiments of each aspect of the invention, the compound having formula (I) has as R 1 Ethyl group, as R 2 Hydrogen, as R 3 difluoromethyl or trifluoromethyl; and as R 4 R with 1 to 3 substituents 5 Substituted phenyl, wherein R 5 It is independently selected from halogens, C1-C3-haloalkyl, C1-C3-haloalkoxy and -OCF2-O-.

[0066] In embodiments of each aspect of the invention, the compound having formula (I) has as R 1 Ethyl group, as R2 Hydrogen, as R 3 difluoromethyl or trifluoromethyl; and as R 4 R with 1 to 2 substituents 5 Substituted phenyl, wherein R 5 It is independently selected from halogens, C1-C3-haloalkyl, C1-C3-haloalkoxy and -OCF2-O-.

[0067] In embodiments of each aspect of the invention, the compound having formula (I) has as R 1 Ethyl group, as R 2 Hydrogen, as R 3 difluoromethyl; and as R 4 A phenyl group substituted with one or two independent substituents selected from fluorine, chlorine, bromine, iodine and -OCF2-O-.

[0068] In a second aspect, the invention makes it possible to obtain a composition comprising a compound having formula (I) as defined in the first aspect, one or more adjuvants and diluents, and optionally one or more other active ingredients.

[0069] In a third aspect, the invention enables the provision of a method for combating and controlling insects, mites, nematodes, or mollusks, the method comprising applying to the pest, the site of the pest, or plants susceptible to pest attack an effective amount of an insecticidal, acaricidal, nematodeic, or molluskic compound as defined in the first aspect or a composition as defined in the second aspect.

[0070] In a fourth aspect, the present invention provides a method for protecting plant propagation material from attacks by insects, mites, nematodes or mollusks, the method comprising treating the propagation material or the site where the propagation material is grown with an effective amount of a compound having formula (I) as defined in the first aspect or a composition as defined in the second aspect.

[0071] In a fifth aspect, the present invention makes it possible to obtain a plant propagation material, such as a seed, which comprises a compound having formula (I) as defined in the first aspect or a composition as defined in the second aspect, or is treated with the compound or the composition, or has the compound or the composition attached thereto.

[0072] In another aspect, the present invention provides a method for controlling parasites internal or external to an animal in need, the method comprising administering an effective amount of the compound of the first aspect. The present invention further provides a method for controlling external parasites in an animal in need, the method comprising administering an effective amount of a compound having formula (I) as defined in the first aspect. The present invention further provides a method for preventing and / or treating diseases transmitted by ectoparasites, the method comprising administering an effective amount of a compound having formula (I) as defined in the first aspect to an animal in need.

[0073] Compounds having formula (I) can be prepared by those skilled in the art using known methods. More specifically, compounds having formula I and their intermediates can be prepared as described below in the schemes and examples. For clarity, certain stereocenters are not specified and are not intended to limit the teaching of these schemes in any way.

[0074] The method according to the invention for preparing compounds having formula (I) is carried out by methods known to those skilled in the art.

[0075] Compounds having formula (I) (where R) 1 R 2 R 3 and R 4 As defined in the first aspect) is new and can be prepared according to scheme 1 by: making acid II (wherein R) 3 and R 4 As defined in the first aspect) and piperazine III (where R 1 and R 2 As defined in the first aspect, a known amide coupling agent (such as 1-[bis(dimethylamino)-methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), propanephosphonic anhydride (T3P), or butanephosphonic anhydride (T4P)) and a base are reacted in a suitable solvent. Suitable bases are, for example, triethylamine, N,N-diisopropylethylamine (Hooning's base), and pyridine. Suitable solvents are, for example, 2-methyltetrahydrofuran, dimethylformamide (DMF), dimethylacetamide (DMA), and ethyl acetate. Instead of piperazine III, corresponding salts of piperazine III, such as chloride or bromide salts of piperazine III, may also be used.

[0076] Option 1:

[0077]

[0078] Alternatively, compounds having formula (I) (where R) 1 R 2 R3 and R 4 As defined in the first aspect, it can be prepared according to scheme 2 by the following method: making acyl chloride IV (wherein R...) 3 and R 4 As defined in the first aspect) and amine III (where R 1 and R 2 As defined in the first aspect, the reaction takes place in the presence of a base (e.g., triethylamine or pyridine) and a suitable solvent (e.g., dichloromethane (DCM), tetrahydrofuran (THF), 2-methyl-tetrahydrofuran (2-methyl-THF) or toluene). Instead of piperazine III, corresponding salts of piperazine III, such as chloride or bromide salts of piperazine III, may also be used.

[0079] Option 2:

[0080]

[0081] Acyl chloride IV (where R) 3 and R 4 As defined in the first aspect, it can be determined according to scheme 3 by the corresponding acid II (where R... 3 and R 4 As defined in the first aspect, it is prepared by treatment with, for example, oxalyl chloride or thionyl chloride in an inert solvent (such as DCM, THF or 2-methyl-THF) at a temperature between 20°C and 100°C, preferably 25°C, in the presence of a catalytic amount of DMF.

[0082] Option 3:

[0083]

[0084] Acid II (where R) 3 and R 4 As defined in the first aspect, it can be prepared according to scheme 4 by the following method: making the corresponding ester V (where R) 3 and R 4 As defined in the first aspect and R a = C1-C6-alkyl) is hydrolyzed under alkaline conditions, for example using inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide or potassium carbonate in water, methanol, ethanol, THF or 2-methyl-THF.

[0085] Option 4:

[0086]

[0087] Ester V (where R) 3 and R 4 As defined in the first aspect, and Ra As previously defined, pyridone VI (where R) can be prepared according to scheme 5 by the following method: 3 As defined in the first aspect and R a As previously defined) and alkylating agent VII (where LG 1 The reaction involves leaving groups, such as halogens (e.g., bromine, chlorine, iodine, or methanesulfonates), reacting in the presence of a base (e.g., an inorganic base such as lithium hydroxide, sodium hydroxide, potassium hydroxide, or potassium carbonate) and a suitable solvent (e.g., water, methanol, ethanol, acetone, THF, 2-methyl-THF, DMF, or toluene). The addition of sodium iodide or a phase-transfer catalyst such as tetrabutylammonium bromide or tetrabutylammonium iodide may be advantageous.

[0088] Option 5:

[0089]

[0090] Alternatively, ester V (where R) 3 and R 4 As defined in the first aspect, and R a As previously defined, pyridine VIII (where R) can be prepared according to scheme 6 by the following method: 3 As defined in the first aspect, and R a As previously defined and LG 2 The leaving group (such as halogens, for example fluorine, bromine, chlorine, iodine, or methanesulfonate) reacts with alcohol IX in the presence of a base (such as sodium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, or potassium carbonate) and a suitable solvent (such as THF, 2-methyl-THF, DMF, or toluene).

[0091] Option 6:

[0092]

[0093] Alternatively, compounds having formula (I) (where R) 1 R 2 R 3 and R 4 As defined in the first aspect, it can be obtained according to scheme 7 via pyridone X (where R... 1 R 2 and R 3 As defined in the first aspect) and alkylating agent VII (wherein LG) 1It is obtained by reacting leaving groups, such as halogens, bromine, chlorine, iodine, or methanesulfonates, in the presence of a base (such as an inorganic base, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, or potassium carbonate) in a suitable solvent (such as water, methanol, ethanol, acetone, THF, 2-methyl-THF, DMF, or toluene). The addition of sodium iodide or a phase-transfer catalyst such as tetrabutylammonium bromide or tetrabutylammonium iodide may be advantageous.

[0094] Option 7:

[0095]

[0096] Alternatively, compounds having formula (I) (where R) 2 R 3 and R 4 As defined in the first aspect, pyridine XI (wherein R) can be prepared according to scheme 8 by the following method: 1 R 2 and R 3 As defined in the first aspect and LG 2 The leaving group (such as halogens, for example fluorine, bromine, chlorine, iodine, or methanesulfonate) reacts with alcohol IX in the presence of a base (such as sodium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, or potassium carbonate) and a suitable solvent (such as THF, 2-methyl-THF, DMF, or toluene).

[0097] Option 8:

[0098]

[0099] Compounds having formula XI (where R 1 R 2 and R 3 As defined in the first aspect and LG 2 (It is a leaving group) can be obtained by treating pyridinone X (where R is a leaving group) with a halogenating agent (such as phosphoryl chloride, oxaloyl chloride, or methanesulfonyl chloride) according to scheme 9. 1 R 2 and R 3 (as defined in the first aspect) to obtain.

[0100] Option 9:

[0101]

[0102] Pyridone X (where R) 1 R 2 and R 3 As defined in the first aspect, it can be prepared according to scheme 10 by the following method: making acid XII (wherein R...) 3As defined in the first aspect) and piperazine III (where R 1 and R 2 As defined in the first aspect, a known amide coupling agent such as HATU and a base (e.g., a humin' base) are reacted in a suitable solvent (e.g., DMF or DMA). Instead of piperazine III, corresponding salts of piperazine III, such as chloride or bromide salts of piperazine III, may also be used.

[0103] Option 10:

[0104]

[0105] Alternatively, compounds having formula X (where R) 1 R 2 and R 3 As defined in the first aspect, it can be prepared according to scheme 11 by the following method: making acyl chloride XIII (wherein R...) 3 As defined in the first aspect) and piperazine III (where R 1 and R 2 (As defined in the first aspect) The reaction takes place in the presence of a base (e.g., triethylamine or pyridine) and a suitable solvent (e.g., DCM, THF, 2-methyl-THF, or toluene). Instead of piperazine III, corresponding salts of piperazine III, such as chloride or bromide salts of piperazine III, may also be used.

[0106] Option 11:

[0107]

[0108] Acyl chloride XIII (where R) 3 As defined in the first aspect, it can be determined according to scheme 12 by the corresponding acid XII (where R... 3 As defined in the first aspect, it is prepared by treatment with, for example, oxalyl chloride or thionyl chloride in an inert solvent (such as DCM, THF or 2-methyl-THF) at a temperature between 20°C and 100°C, preferably 25°C, in the presence of a catalytic amount of DMF.

[0109] Option 12:

[0110]

[0111] Acid XII (where R) 3 As defined in the first aspect, it can be prepared by making the corresponding ester XIV (where R) into a powder. 3 As defined in the first aspect and R a(C1-C6-alkyl) under alkaline conditions, for example using inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, or potassium carbonate in water, methanol, ethanol, THF, or 2-methyl-THF, as shown in Scheme 13. Esters having formula XIV (where R) 3 As defined in the first aspect, and R a As previously defined, it is known in the literature (e.g., Y. Xie et al., Pest Manag. Sci. [Science of Pest Management] 2017, 73, 945-952) or can be prepared by those skilled in the art.

[0112] Option 13:

[0113]

[0114] Piperazine III (of which R 1 and R 2 As defined in the first aspect, compound XV can be prepared according to scheme 14 by treating it with an acid (e.g., hydrochloric acid, hydrobromic acid, or trifluoroacetic acid) in a suitable solvent (e.g., methanol, ethanol, ethyl acetate, DCM, THF, 2-methyl-THF, or toluene) at a temperature between 20°C and 80°C, preferably between 20°C and 30°C. 1 and R 2 (As defined in the first aspect). Depending on the post-treatment, a corresponding salt of piperazine III may be obtained, such as a chloride or bromide salt of piperazine III instead of piperazine III.

[0115] Option 14:

[0116]

[0117] Piperazine XV (where R 1 and R 2 As defined in the first aspect, it can be prepared according to scheme 15 by reacting compound XVI with sulfonyl chloride XVII (wherein R... 1 and R 2 (As defined in the first aspect) the reaction is carried out in a suitable solvent (e.g., acetonitrile, ethyl acetate, DCM, THF, 2-methyl-THF or toluene) at a temperature between 20°C and 80°C, preferably between 20°C and 30°C.

[0118] Option 15:

[0119]

[0120] Alternatively, piperazine XV (where R 1 and R2 As defined in the first aspect, compound XVI can be prepared according to scheme 16 by first reacting it with thiocyanate chloride, followed by reacting it with amine XIX (wherein R...). 1 and R 2 (As defined in the first aspect) the reaction is carried out in a suitable solvent (e.g., acetonitrile, ethyl acetate, DCM, THF, 2-methyl-THF or toluene) at a temperature between 20°C and 80°C, preferably between 20°C and 30°C.

[0121] Option 16:

[0122]

[0123] The compounds having formula (I) according to Tables 1 to 4 below can be prepared according to the methods described above. The following examples are intended to illustrate the invention and show preferred compounds having formula (I) (in the form of compounds having formula (Ia)).

[0124] (Ia)

[0125] Each of Tables 1 through 4 following Table M includes 62 compounds having formula (Ia), where R 2 and R 5 It has the values ​​given in each row of table M, and R 3 It has the values ​​given in the relevant tables 1 to 4.

[0126] Therefore, compound 1.1 corresponds to a compound having formula (Ia), where R 2 and R 5 As defined in the first row of Table M, and where R 3 As defined in Table 1; compound 4.10 corresponds to a compound having formula (Ia), where R 2 and R 5 As defined in row 10 of table M, and where R 3 As defined in Table 4; etc.

[0127] Table M:

[0128]

[0129] Table 1: The table discloses 62 compounds with formula (Ia) from 1.1 to 1.62, of which R 3 It is methyl and R 2 and R 5As defined in Table M. For example, compound number 1.1 has the following structure:

[0130] (1.1)

[0131] Table 2 The table discloses 62 compounds having formula (Ia) 2.1 to 2.62, of which R 3 It is difluoromethyl and R 2 and R 5 As defined in Table M.

[0132] Table 3 The table discloses 62 compounds having formula (Ia) 3.1 to 3.62, of which R 3 It is trifluoromethyl and R 2 and R 5 As defined in Table M.

[0133] Table 4 The table discloses 62 compounds having formula (Ia) 4.1 to 4.62, of which R 3 It is cyclopropyl and R 2 and R 5 As defined in Table M.

[0134] It also makes it possible to obtain certain intermediate compounds having the formulas Xa and XI-a, some of which are novel.

[0135] Therefore, in this paper, we can obtain:

[0136] Compounds having formula Xa

[0137] Xa

[0138] Where R 2 and R 3 As defined in the first aspect; in the embodiments, R 2 It is hydrogen or methyl and R 3 It is methyl, difluoromethyl, trifluoromethyl, or cyclopropyl;

[0139] XI-a compounds

[0140] XI-a

[0141] Where R 2 and R 3 As defined in the first aspect; in the embodiments, R 2 It is hydrogen or methyl, R 3 It is methyl, difluoromethyl, trifluoromethyl, or cyclopropyl; and LG 2 It is chlorine, bromine, or fluorine.

[0142] The compounds of formula (I) according to the invention are active ingredients with preventative and / or therapeutic value in the field of pest control. Even at low application rates, they possess a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish, and plants. The active ingredients according to the invention act on all or individual developmental stages of normally susceptible and resistant animal pests (such as insects or representatives of mites). The insecticidal or acaricidal activity of the active ingredients according to the invention can manifest directly, i.e., immediate or only after some time (e.g., during molting), causing damage to pests; or indirectly, for example, by reducing oviposition and / or hatching rates.

[0143] Examples of animal pests mentioned above are:

[0144] From the order Acari, for example,

[0145] Species of the genera *Acalitus* spp., *Aculus* spp., *Acaricalus* spp., *Aceria* spp., *Acarus siro*, *Amblyomma* spp., *Argas* spp., *Boophilus* spp., *Brevipalpus* spp., *Bryobia* spp., *Calipitrimerus* spp., *Chorioptes* spp., *Dermanyssusgallinae*, *Dermatophagoides* spp., *Eotetranychus* spp., and *Eriophyes*. Species of the genera *Hemitarsonemus*, *Hyalomma*, *Ixodes*, *Olygonychus*, *Ornithodoros*, *Polyphagotarsone latus*, *Panonychus*, *Phyllocoptruta oleivora*, *Phytonemus*, *Polyphagotarsonemus*, *Psoroptes*, *Rhipicephalus*, *Rhizoglyphus*, and *Sarcoptes*. spp.), species of the genera *Steneotarsonemus*, *Tarsonemus*, and *Tetranychus*;

[0146] From lice, for example,

[0147] Species of the genera *Haematopinus* spp., *Linognathus* spp., *Pediculus* spp., *Pemphigus* spp., and *Phylloxera* spp.;

[0148] From Coleoptera, for example,

[0149] Species of the genera *Agriotes* spp., *Amphimallon majale*, *Anomala orientalis*, *Anthonomus* spp., *Aphodius* spp., *Astylus atromaculatus*, *Ataenius* spp., *Atomaria linearis*, *Chaetocnema tibialis*, *Cerotomas* spp., *Conoderus* spp., *Cosmopolites* spp., *Cotinis nitida*, *Curculio* spp., *Cyclocephalas* spp., *Dermestes* spp., and *Diabrotica*. spp.), Argentine rhinoceros beetle (Diloboderus abderus), species of ladybugs (Epilachna spp.), species of Eremnus, black cane beetle (Heteronychus arator), coffee berry beetle (Hypothenemus hampei), Lagria vilosa, potato beetle (Leptinotarsa ​​decemlineata), rice weevils (Lissorhoptrus spp.), species of Liogenys, species of Maecolaspis, chestnut velvet beetle (Maladera castanea), American leaf beetle (Megascelis spp.), rapeseed flower beetle (Melighetes aeneus), dwarf beetle (Melolontha spp.), Myochrousarmatus, sawmill beetle (Orycaephilus spp.), ear-beaked beetle (Otiorhynchus spp.), dwarf beetle (Phyllophaga) spp.), species of the genus *Phlyctinus*, species of the genus *Popillia*, species of the genus *Psylliodes*, species of the genus *Rhyssomatus aubtilis*, species of the genus *Rhizopertha*, species of the family Scarabidae, species of the genus *Sitophilus*, and species of the genus *Sitotroga*.), species of the genera *Somaticus*, *Sternechus subsignatus*, *Tenebrio*, *Tribolium*, and *Trogoderma*.

[0150] From the order Diptera, for example,

[0151] Species of the genera *Aedes*, *Anopheles*, *Antherigonasoccata*, *Bactrocea oleae*, *Bibio hortulanus*, *Bradysia*, *Calliphora erythrocephala*, *Ceratitis*, *Chrysomyia*, *Culex*, *Cuterebra*, *Dacus*, *Delia*, *Drosophila melanogaster*, *Fannia*, *Gastrophilus*, *Geomyza tripunctata*, and *Glossina*. Species of the genera *Hypodermas*, *Hyppobosca*, *Liriomyza*, *Lucilia*, *Melanagromyza*, *Musca*, *Oestrus*, *Orseolia*, *Oscinella frit*, *Pegomyia hyoscyami*, *Phorbia*, *Rhagoletis*, *Rivelia quadrifasciata*, *Scatella*, *Sciara*, *Stomoxys*, *Tabanus*, and *Tannia*. spp.) and species of the genus Tipula spp.;

[0152] From Hemiptera, for example,

[0153] *Acanthocoris scabrator*, *Acrosternum* species, *Adelphocoris lineolatus*, *Aleurodes* species, *Amblypeltanitida*, *Bathycoelia thalassina*, *Clavigralla* species, *Creontiades* species, *Dichelops furcatus*, *Edessa* species, *Euchistus* species, *Eurydema pulchrum*, *Platyscutella* species, *Tea-winged Bug*, *Horcias* *Nobilellus*, *Rhizophora*, *Nesidiocoris*, *Nesidiocoris tenuis*, *Nesidiocoris*, *Nesidiocoris simulans ...

[0154] Pea webless long-tubed aphid (Acyrthosium pisum), species of the genus *Adalges*, *Agalliana ensigera*, *Talguiron vein psyllid*, species of the genus *Aleurodicus*, species of the genus *Aleurocanthus*, sugarcane hole whitefly, soft-haired whitefly (*Aleurothrixus floccosus*), cabbage whitefly (*Aleyrodes brassicae*), cotton leafhopper (*Amarasca biguttula*), lemon long-spotted leafhopper, species of the genus *Nephrodisiac*, aphids, species of the genus *Aspidiotus*, *Achyranthes aphid*, potato / tomato psyllid (*Bactericera cockerelli*), species of the genus *Small whitefly*, species of the genus *Brachycaudus*, cabbage aphid, species of the genus *Cavariella*, etc. *Aegopodii Scop.*, *C.* species, *C.* species, *C.* species, *C.* species, *C.* species, *C.* species, *C.* species, *C.* species, *C.* species, *C.* soft scale, *C.* yellow-winged corn leafhopper, *C.* species, *C.* citrus psyllid, *C.* species, *C.* species, *C.* species, *C.* species, *C.* species, *C.* woolly aphid, *C.* species ... erysimi), Lyogenys maidis, species of the genus *Lyogenys*, species of the genus *Lyogenys*, species of the genus *Metcalfa pruinosa*, *Metcalfa pruinosa*, *Metcalfa pruinosa*, *Metcalfa pruinosa*, *Metcalfa pruinosa*, *Metcalfa pruinosa*, species of the genus *Metcalfa pruinosa*, species of the genus *Neotoxoptera*, species of the genus *Neotoxoptera*, species of the genus *Neotoxoptera*, and species of the genus *Nilaparvata*.), Pear Green Aphid, Odonaspis ruthae, Sugarcane Cotton Aphid, Myrica Marginata Whitefly, Coxsackia, Species of the genus *Pseudatomoscelis*, Species of the genus *Gallus*, Corn Lanternfly, Species of the genus *Phylloxera*, Species of the genus *Phylloxera*, Species of the genus *Pseudatomoscelis*, Species of the genus *Pulvinaria*, Species of the genus *Pulvinaria*, Species of the genus *Pulvinaria*, Species of the genus *Quesada gigas*, Species of the genus *Recilia dorsalis*, Species of the genus *Pseudocybe ... *Festinus*, *Tarophagus Proserpina*, species of *Aphid*, species of *Whitefly*, *Tridiscus sporoboli*, species of *Trionymus* spp., African psyllid, arrowhead scale, flame leafhopper, *Zyginidia scutellaris*.

[0155] From Hymenoptera, for example,

[0156] Species from the genera *Acromyrmex*, *Arge* spp., *Attaspp.*, *Cephus* spp., *Diprion* spp., *Diprionidae*, *Gilpinia polytoma*, *Hoplocampa* spp., *Lasius* spp., *Monomorium pharaonis*, *Neodiprions* spp., *Pogonomyrmex* spp., *Solenopsis* spp., and *Vespa* spp.;

[0157] From the order Isoptera, for example,

[0158] Species of the genera *Coptotermes* spp., *Corniternes cumulans*, *Incisitermes* spp., *Macrotermes* spp., *Mastotermes* spp., *Microtermes* spp., and *Reticulitermes* spp.; tropical fire ant (*Solenopsis geminate*).

[0159] From the order Lepidoptera, for example,

[0160] Species of the genera *Longwinged Roller*, *Brown-banded Roller*, *Clearwing Moth*, *Noctuid Moth*, cotton leafhopper, *Amylois*, *Lysimachia*, *Yellow Roller*, *Argyresthia spp.*, *Betweenleaf Roller*, *Striped Roller*, cotton leafminer, corn leafminer, powdery leafminer, peach fruit borer, *Grass borer*, *Colored Roller*, *Chrysoteuchia topiaria*, grape fruit borer, *Leaf Roller*, *Cloud Roller*, *Striped Roller*, *Sheath Moth*, *Colias lesbia*, *Cosmophila* *Flava* species, including *Catharanthus*, *Catharanthus*, *Catharanthus*, *Catharanthus*, *Catharanthus*, *Catharanthus*, *Catharanthus*, *Catharanthus*, *Catharanthus*, *Catharanthus*, *Catharanthus*, *Elasmopalpus*, *Elasmopalpus*, *Catharanthus*, *Epinotia*, *Estigmene acrea*, *Etiellazinckinella*, *Estigmene ... *Lignosellus*, *Leaf Miner*, *Leaf Miner* species, *Grape Flower Roller*, *Loxostege bifidalis*, *Tortoise Moth* species, *Minter* species, *Malacosoma* spp., *Cabbage Noctuid*, *Tobacco Hawk Moth*, *Mythimna* spp., *Noctuid* species, *Autumn Geyser* species, *Orniodes indica*, European Corn Borer, *Small Leaf Roller* species, *Brown Leaf Roller* species, *Small-eyed Noctuid*, *Stem-boring Noctuid*, *Red Bollworm*, *Coffee Leaf Miner*, *One-spotted Armyworm*, *Potato Leaf Moth*, *Cabbage White*, *White Leaf Butterfly* species, *Plutella xylostella*, *Small White Nest Moth* species, *Geometrid Leaf Moth* species, *Rachiplusianu*, *Richia albicosta*, *Scirpophaga* species spp.), species of the genera *Steel borer*, *Long-haired leafroller*, *Grey-winged leafroller*, *Cotton leafroller*, *Clearwinged moth*, *Heterodactylus*, *Rollerella*, *Powdered moth*, *Tomato leafminer*, and *Ophiopogon*.

[0161] From the order Mallophaga, for example,

[0162] Species of the genera *Damalinea* and *Trichodectes*.

[0163] From the order Orthoptera, for example,

[0164] Species of the genera *Blatta*, *Blattella*, *Gryllotalpa*, *Leucophaea maderae*, *Locusta*, *Neocurtilla hexadactyla*, *Periplaneta*, *Scapteriscus*, and *Schistocerca*.

[0165] From the order Psocoptera, for example,

[0166] Species of the genus *Liposcelis*;

[0167] From the order Siphonaptera, for example,

[0168] Species of the genera *Ceratophyllus* spp., *Ctenocephalides* spp., and *Xenopsylla cheopis*;

[0169] From the order Thysanoptera, for example,

[0170] Calliothrips phaseoli, species of the genus *Frankliniella*, species of the genus *Heliothrips*, species of the genus *Hercinothrips*, species of the genus *Parthenothrips*, species of the genus *Scirtothrips aurantii*, species of the genus *Sericothrips*, species of the genus *Taeniothrips*, and species of the genus *Thripsspp*.

[0171] From the order Thysanura, for example, silverfish (Lepisma saccharina).

[0172] In another aspect, the present invention may also relate to a method for controlling damage to plants and their parts caused by plant parasitic nematodes (endoparasitic, semi-endoparasitic, and ectoparasitic nematodes), particularly the following plant parasitic nematodes: root knot nematodes, northern root knot nematode (Meloidogyne hapla), southern root knot nematode (Meloidogyne incognita), Javan root knot nematode (Meloidogyne javanica), peanut root knot nematode (Meloidogyne arenaria), and other root knot nematode species; cyst-forming nematodes, potato golden nematode (Globodera rostochiensis), and other Globodera species; cereal cyst nematode (Heterodera avenae), soybean cyst nematode (Heteroderaglycines), and beet cyst nematode (Heterodera... *Heterodera trifolii* and other species of the genus *Heterodera*; *Seed gall nematodes* and *Anguina* species; *Stem and foliar nematodes* and *Aphelenchoides* species; *Sting nematodes*, *Belonolaimus longicaudatus* and other species of the genus *Belonolaimus*; *Pine nematodes*, *Bursaphelenchus xylophilus* and other species of the genus *Bursaphelenchus*; *Ring nematodes*. Species of the genera *Criconema*, *Criconemella*, *Criconemoides*, and *Mesocriconema*; *Stemand bulb nematodes*, *Ditylenchus destructor*, *Ditylenchus dipsaci*, and other *Ditylenchus* species; *Awl nematodes* and *Dolichodorus* species;Spiral nematodes, Heliocotylenchus multicinctus and other species of the genus *Helicotylenchus*; Sheath and sheathoid nematodes, species of the genus *Hemicycliophora* and *Hemicriconemoides*; species of the genus *Hirshmanniella*; species of the genus *Lancenematodes* and *Hoploaimus*; species of the genus *false rootknot nematodes* and *Nacobbus*; Needle nematodes, Longidoruselongatus and other species of the genus *Longidorus*; Pin nematodes and species of the genus *Pratylenchus*; Lesion nematodes. *Pratylenchus neglectus*, *Pratylenchus penetrans*, *Pratylenchus curvitatus*, *Pratylenchus goodeyi*, and other species of the genus *Pratylenchus*; *Burrowing nematodes*, *Radipholus similis*, and other species of the genus *Radipholus*; *Reniform nematodes*, *Rotylenchus robustus*, *Rotylenchus reniformis*, and other species of the genus *Rotylenchus*; species of the genus *Scutellonema*; *Stubby root nematodes*, *Trichodorus*. primitivus) and other species of the genus *Trichodorus*, species of the genus *Paratrichodorus*; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other species of the genus *Tylenchorhynchus*;Citrus nematode species (Citrus nematodes, Tylenchulus); Dagger nematodes and Xiphinema species; and other plant-parasitic nematode species, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.

[0173] The compounds of this invention may also have activity against mollusks. Examples include, for instance, the families Pomacea canaliculata (golden apple snail); Arion (black slug (A. ater), A. circumscriptus, A. hortensis, A. rufus)); Bradybaenidae (shrub snail (Bradybaena fruticum)); Cepaea (garden snail (C. hortensis, forest snail (C. Nemoralis)); ochlodina; Deroceras (grey slug (D. agrestis), D. empiricorum, D. laeve, D. reticulatum)); and Discus (round disc snail (D.). *Galba* (G. trunculata); *Helicelia* (H. itala, H. obvia); *Helicidae* (Helicigona arbustorum); *Helicodiscus*; *Helix* (H. aperta); *Limax* (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus); *Lymnaea*; *Milax* (M. black slug). gagates), marginal slug (M. marginatus), sowerbyi slug (M. sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.

[0174] The active ingredients according to the invention can be used to control, i.e., to suppress or destroy pests of the types described above, which are particularly found on plants, especially useful and ornamental plants in agriculture, horticulture and forestry, or on the organs of such plants, such as fruits, flowers, leaves, stems, tubers or roots, and in some cases, even plant organs formed at a later point in time remain protected against these pests.

[0175] Specifically, suitable target crops include: cereals such as wheat, barley, rye, oats, rice, corn, or sorghum; sugar beets such as sugar beets or forage beets; fruits such as pome, stone fruits, or seedless small fruits such as apples, pears, plums, peaches, apricots, cherries, or berries such as strawberries, raspberries, or blackberries; legumes such as beans, lentils, peas, or soybeans; and oilseed crops such as rapeseed, mustard, poppies, olives, sunflowers, coconuts, castor beans, and cocoa. Beans or peanuts; cucurbits such as pumpkins, cucumbers, or melons; fiber plants such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits, or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, or bell peppers; Lauraceae, such as avocados, cinnamon, or camphor; and also tobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines, hops, plantains, and latex plants.

[0176] In a specific embodiment, the compound having formula (I) controls mites, rust mites and leaf mites selected from vegetables (especially tomatoes and gourds), citrus fruits, pome fruits, stone fruits, nuts, cotton, tropical crops, avocados, ornamental plants, beans, soybeans, strawberries and grapes, as well as trees and plants.

[0177] The compositions and / or methods of the present invention can also be used on any ornamental plants and / or vegetable crops (including flowers, shrubs, broad-leaved trees and evergreens).

[0178] For example, this invention can be used for any of the following ornamental plant species: *Ageratum* species, *Alonsoa* species, *Anisodontea capsenisis* species, *Chrysanthemum* species, *Snapdragon* species, *Aster* species, *Begonia* species (e.g., *Begonia riegerii*, *Begonia semperflorens*, *Begonia tubéreux*), *Bougainvillea* species, *Brachycome* species, *Brachycome* species (ornamental plants), *Pueraria* species, pepper, periwinkle, *Canna* species, *Cornflower* species, *Chrysanthemum* species, *Cinnamomum maritime* species, *Coreopsis* species, *Crassula coccinea*, *Cuphea ignea*, *Dahlia* species, *Delphinium* species, bleeding heart, *Dorotheantus* species. spp.), lisianthus, forsythia species, fuchsia species, geranium gnaphalium, semperflorens species, globe amaranth, heliotrope species, sunflower species, hibiscus species, hydrangea species, hydrangea species, crape myrtle species, impatiens species (African impatiens), Iresines spp., kalanchoe species, lantana, Marchflower, lion's ear flower species, lily species, pine needle chrysanthemum species, ground cherry species, peppermint species, dragon's face chrysanthemum species, marigold species, carnation species, canna species, oxalis species, daisy species, geranium species (shield geranium, horseshoe geranium), violet species (pansy), petunia species, oleander species, sedum species. spp.), species of the genera *Poinsettia*, *Parthenocissus* (including five-leafed Parthenocissus and Virginia creeper), species of the genera *Primula*, *Rhododendron*, species of the genera *Rosa*, species of the genera *Datura*, species of the genera *Viola*, species of the genera *Salvia*, *Scaevola aemola*, *Schizanthus wisetonensis*, species of the genera *Sedum*, species of the genera *Solanum*, species of the genera *Surfinia*, species of the genera *Marigold*, species of the genera *Nicotiana*, species of the genera *Verbena*, species of the genera *Zinnia*, and other bedding plants.

[0179] For example, this invention can be used for any of the following vegetable species: Allium (garlic, onion, shallot (A. oschaninii), leek, scallion, green onion), parsley, celery, asparagus, beet, Brassica (cabbage, Chinese cabbage, turnip), chili, chickpea, endive, chicory (chicory, endive), watermelon, cucumber (cucumber, melon), squash (zucchini, squash), artichoke (artichoke, spiny artichoke), carrot, fennel, St. John's wort, lettuce, tomato (tomato, cherry tomato), mint, basil, parsley, common bean (bean, green bean), pea, radish, edible rhubarb, rosemary, sage, black ginseng, eggplant, spinach, neovalerian (lettuce valerian, V. eriocarpa), and broad bean.

[0180] Preferred ornamental plant species include African violet, Begonia, Dahlia, Sedum, Hydrangea, Verbena, Rosa, Kalanchoe, Poinsettia, Aster, Cornflower, Coreopsis, Delphinium, Mentha, Oleander, Yellow Daisy, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Sage, Hydrangea, Rosemary, Sage, St. John's Wort, Mint, Sweet Pepper, Tomato, and Cucumber.

[0181] The active ingredients according to the invention are particularly suitable for controlling bean aphids, cucumber leaf beetles (Diabrotica balteata), tobacco shoot borers, peach aphids, diamondback moths, and sea gray winged moths (Spodoptera littoralis) on cotton, vegetables, corn, rice, and soybean crops. These active ingredients according to the invention are also particularly suitable for controlling cabbage borers (preferably on vegetables), codling moths (preferably on apples), small green leafhoppers (preferably in vegetables and vineyards), potato leaf beetles (Leptinotarsa) (preferably on potatoes), and rice stem borers (preferably on rice).

[0182] Compounds having formula (I) are particularly suitable for controlling mites, spider mites, and rust mites, such as species of the genus *Vepithecus*; *Vepithecus var. var.*; *Vepithecus var. coccinea*; *Vepithecus* species; *Citrus gallisepticus*; *Ixodes citrinum*; *Ixodes citrinum*; *Ixodes squarrosa*; *Ixodes squarrosa* species; *Pseudo-agilea*; *Ixodes brevicornu* species; *Ixodes purpureus*; *Ixodes squarrosa*; *Ixodes squarrosa*; *Ixodes squarrosa* species; *Ixodes squarrosa* species; *Ixodes squarrosa* species; *Ixodes squarrosa* species; *Ixodes squarrosa* species; *Ixodes squarrosa* species; *Ixodes squarrosa* species; *Demodex bovis*; *Demodex* *cacalli*; canine demodicus; goat demodicus; horse demodicus; sheep demodicus; species of the genus *Demodex*; pig demodicus; chicken spiny mite; species of the genus *Spirodactylus*; species of the genus *Tetranychus*; *Tetranychus spp.*; pear gall mite; tea gall mite; species of the genus *Tetranychus*; grape gall mite; species of the genus *Tetranychus*; *Halotydeus destructor*; species of the genus *Halotydeus ... ilicis); species of the genus *Spodoptera*; species of the genus *Ceratophora*; species of the genus *Ceratophora*; species of the genus *Ceratophora*; species of the genus *Ceratophora*; species of the genus *Otorrhea*; species of the genus *Psorergates ... rupicaprae); species of the genus *Sarcasmium*; *Sarcasmium suis*; *Sarcasmium stenotarsii*; species of the genus *Sarcasmium stenotarsii*; species of the genus *Sarcasmium*; species of the genus *Tetranychus cinnabarinus*; *Tetranychus kansawa*; species of the genus *Tetranychus*; *Tetranychus two-spotted*; *Tetranychus rubrum*; species of the genus *Tetranychus ...

[0183] In the embodiments, compounds having formula (I) are particularly suitable for controlling one or more of the following: Citrus gall mite; Aculus lycopersici; Aculus pilosa; Aculus skeletalus; Aculus purpuratus; species of the genus Aculus; fruit moth; Carpinus hornbeam; species of the genus Aculus; pear gall mite; Eriophyes piri; species of the genus Eriophyes; grape gall mite; African true spider mite; Oriental true spider mite; meadow claw mite; Citrus psoriid; Apple claw mite; grape rust mite; Citrus rust mite; Lateral tarsiers; Carmine spider mite; Tetranychus kamizawa; species of the genus Tetranychus; and Tetranychus two-spotted.

[0184] In another embodiment, compounds having formula (I) are particularly suitable for controlling one or more of the following: Citrus gall mite; Piper's needle gall mite; *Eriophyes piri*; species of the genus *Eriophyes*; *Eriophyes piri*; *Eriophyes gracilis*; *Tetranychus africanus*; *Tetranychus orientalis*; *Tetranychus gracilis*; *Tetranychus maculata*; *Tetranychus gracilis*; *Tetranychus citrinum*; *Tetranychus lateralis*; *Tetranychus carmineus*; *Tetranychus kamizawa*; species of the genus *Tetranychus*; and *Tetranychus two-spotted*.

[0185] The term "crop" should be understood to also include crop plants that have been transformed using recombinant DNA technology to enable them to synthesize one or more selectively acting toxins, such as those known to originate from toxin-producing bacteria, particularly those of the genus Bacillus.

[0186] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, such as those from Bacillus cereus or Bacillus spp.; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins from nematode-parasitic bacteria, such as species of the genus Photorhabdus or species of the genus Xenorhabdus, such as Photorhabdus luminescens and Xenorhabdus. (nematophilus); toxins produced by animals, such as scorpion venom, spider venom, bee venom, and other insect-specific neurotoxins; toxins produced by fungi, such as streptotoxins; lectins, such as pea lectin, barley lectin, or snowdrop lectin; agglutinin; protease inhibitors, such as trypsin inhibitors, serine inhibitors, potato glycoproteins, cystatin, and papain inhibitors; ribosome-inactivating proteins (RIPs), such as ricin, maize-RIP, absinthecin, loofah seed toxin, saponin toxin, or cassia root toxin; steroid metabolic enzymes, such as 3-hydroxysteroid oxidase, decidual steroid-UDP-glycosyltransferase, cholesterol oxidase, decidualin inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase, and glucanase.

[0187] In the context of this invention, δ-endotoxins (e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C) or vegetative insecticidal proteins (Vip) (e.g., Vip1, Vip2, Vip3, or Vip3A) should be understood to obviously also include mixed toxins, truncated toxins, and modified toxins. Mixed toxins are generated by recombination of new combinations of different domains of those 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 naturally occurring toxin are substituted. In such amino acid substitutions, it is preferable to insert a non-naturally occurring protease recognition sequence into the toxin, for example, as in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0188] Examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0 374753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073.

[0189] Methods for preparing such transgenic plants are generally known to those skilled in the art and are described in, for example, the disclosures mentioned above. CryI type deoxyribonucleic acid and its preparation are known, for example, from WO 95 / 34656, EP-A-0 367474, EP-A-0 401 979 and WO 90 / 13651.

[0190] Toxins contained in genetically modified plants confer tolerance to harmful insects. Such insects can exist in any insect taxonomy, but are particularly common in beetles (Coleoptera), dipterans (Diptera), and moths (Lepidoptera).

[0191] Transgenic plants containing one or more genes encoding insecticidal resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants are: YieldGard® (a corn variety expressing Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing both Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing Cry9C toxin); Herculex I® (a corn variety expressing Cry1Fa2 toxin and the enzyme phosphatidylin N-acetyltransferase (PAT) for acquiring resistance to the herbicide glufosinate-ammonium); NuCOTN 33B® (a cotton variety expressing Cry1Ac toxin); Bollgard I® (a cotton variety expressing Cry1Ac toxin); Bollgard II® (cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate resistance trait), Agrisure® CBAdvantage (Bt11 corn borer (CB) trait), and Protecta®.

[0192] Another example of such genetically modified crops is:

[0193] 1. Bt11 corn, from Syngenta Seeds SAS, Cheminde l'Hobit 27, F-31 790 St. Sauveur, France, Registry No. C / FR / 96 / 05 / 10. A genetically modified corn variety that expresses a truncated Cry1Ab toxin to resist the European corn borer (corn borer and mealybug). Bt11 corn is also transgenic to express the PAT enzyme for tolerance to the herbicide glufosinate.

[0194] 2. Bt176 corn, from Syngenta Seed Company, 27 Hobbit Road, F-31 790 Saint-Soville, France, Registry No. C / FR / 96 / 05 / 10. A genetically modified corn variety that expresses the Cry1Ab toxin transgenic to resist the European corn borer (corn borer and mealybug). Bt176 corn is also transgenic to express the enzyme PAT for tolerance to the herbicide glufosinate.

[0195] 3. MIR604 corn, from Syngenta Seed Company, 27 Hobbit Road, F-31 790 Saint-Soville, France, Registry No. C / FR / 96 / 05 / 10. A transgenic corn variety resistant to insects by expressing a modified Cry3A toxin. This toxin is modified by inserting a cathepsin-G-protease recognition sequence, Cry3A055. The preparation of such transgenic corn plants is described in WO 03 / 018810.

[0196] 4. MON 863 corn, from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses Cry3Bb1 toxin and is resistant to certain Coleoptera.

[0197] 5. IPC 531 cotton, from Monsanto Europe, 270-272 Teflon Boulevard, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0198] 6.1507 maize, from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, Registry No. C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1F to acquire resistance to certain lepidopteran insects and expressing the PAT protein to acquire tolerance to the herbicide glufosinate.

[0199] 7. NK603 × MON 810 corn, from Monsanto Europe, 270-272 Boulevard de Tverren, B-1150 Brussels, Belgium, Registry No. C / GB / 02 / M3 / 03. This hybrid corn variety was created by crossing the genetically modified cultivar NK603 with MON 810, using conventional breeding methods. NK603 × MON 810 transgenic corn expresses the protein CP4 EPSPS obtained from the Agrobacterium strain CP4, conferring resistance to the herbicide Roundup® (containing glyphosate), and also contains the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. Kurstak, conferring resistance to certain lepidopteran insects, including the European corn borer.

[0200] Transgenic crops of insect-resistant plants were also described in BATS (Zentrum für Biosicherheit und Nachhaltigkeit, BATS Center, Clarastrasse 13, Basel 4058, Switzerland) report 2003. http: / / bats.ch )middle.

[0201] The term "crop" should be understood to also include crop plants that have been transformed using recombinant DNA technology to enable them to synthesize selectively active resistance substances, such as so-called "pathogenesis-associated proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such resistance substances and transgenic plants capable of synthesizing such resistance 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 in, for example, the disclosures mentioned above.

[0202] Crops can also be modified to enhance their resistance to pathogens such as fungi (e.g., Fusarium, Anthracnose, or Phytophthora), bacteria (e.g., Pseudomonas), or viruses (e.g., Potato Leaf Roll Virus, Tomato Spotted Wilt Virus, Cucumber Mosaic Virus).

[0203] Crops also include those that have enhanced resistance to nematodes such as the soybean heterodermal nematode.

[0204] Crops that are tolerant to abiotic stresses include those that exhibit enhanced tolerance to drought, high salinity, high temperature, cold, frost, or light radiation, for example, through the expression of NF-YB or other proteins known in the art.

[0205] Antipathogenic substances that can be expressed by such transgenic plants include, for example, ion channel blockers, such as sodium and calcium channel blockers, such as viral KP1, KP4 or KP6 toxins; stilbene synthase; bibenzyl synthase; chitinase; glucanase; so-called "pathogenesis-associated proteins" (PRP; see, for example, EP-A-0 392 225); antipathogenic substances produced by microorganisms, such as peptide antibiotics or heterocyclic antibiotics (see, for example, WO 95 / 33818) or proteins or polypeptide factors involved in plant pathogen defense (so-called "plant disease resistance genes", as described in WO 03 / 000906).

[0206] Another area of ​​use for the compositions according to the invention is the protection of stored articles and storage rooms, as well as the protection of raw materials such as timber, textiles, flooring, or buildings, and also in the field of hygiene, particularly the protection of humans, livestock, and productive animals from pests of the types mentioned.

[0207] This invention provides compounds for use in a first aspect of therapy. This invention provides compounds for controlling parasites internal or external to an animal. This invention further provides compounds for controlling ectoparasites in an animal. This invention further provides compounds for preventing and / or treating diseases transmitted by ectoparasites.

[0208] This invention provides the use of the compound of the first aspect in the manufacture of a medicament for controlling parasites inside or outside the body of animals. This invention further provides the use of the compound of the first aspect in the manufacture of a medicament for controlling ectoparasites in animals. This invention further provides the use of the compound of the first aspect in the manufacture of a medicament for preventing and / or treating diseases transmitted by ectoparasites.

[0209] This invention provides the use of the compound of the first aspect in controlling parasites inside or on the surface of animals. This invention further provides the use of the compound of the first aspect in controlling ectoparasites of animals.

[0210] When used in the context of parasites inside or on the surface of an animal, the term "control" refers to reducing the number of pests or parasites, eliminating pests or parasites, and / or preventing further infestation by pests or parasites.

[0211] When used in the context of parasites inside or on the surface of an animal, the term "treatment" refers to the suppression, mitigation, cessation, or reversal of the progression or severity of existing symptoms or disease.

[0212] When used in the context of parasites inside or on the surface of an animal, the term "prevention" refers to the avoidance of the development of symptoms or disease in the animal.

[0213] When used in the context of parasites inside or on the body of an animal, the term "animal" can refer to both mammals and non-mammals, such as birds or fish. In the case of mammals, it can be either human or non-human mammals. Non-human mammals include, but are not limited to, livestock and pets. Livestock include, but are not limited to, cattle, camels, pigs, sheep, goats, and horses. Pets include, but are not limited to, dogs, cats, and rabbits.

[0214] Parasites are harmful organisms that live inside or on the surface of a host animal and benefit from it by obtaining nutrients at the expense of the host. Internal parasites are parasites that live inside the body of a host animal. External parasites are parasites that live on the surface of the body of a host animal. External parasites include, but are not limited to, ticks, insects, and crustaceans (such as sea lice). The subclass Ticks (or Acari) includes ticks and mites. Ticks include, but are not limited to, members of the following genera: *Rhipicaphalus*, such as *Rhipicaphalus microplus* (Boophilus microplus) and *Rhipicephalus sanguineus*; *Amblyomrna*; *Dermacentor*; *Haemaphysalis*; *Hyalomma*; *Ixodes*; *Rhipicentor*; *Margaropus*; *Argas*; *Otobius*; and *Ornithodoros*. Mites include, but are not limited to, members of the following genera: *Dermatophytes*, such as *Mammillaria vesicola*; *Ophiopogon*, such as *Mammillaria gravidae*; *Ceratophytes*; *Dermatophytes*, such as *Dermatophytes gravidae*; *Ortnithonyssus*; *Demodex*, such as *Demodex canis*; *Scabies*, such as *Scabies mansii*; and *Scabies*. Insects include, but are not limited to, members of the following orders: *Fleas*, *Diptera*, *Liceta*, *Lepidoptera*, *Coleoptera*, and *Homoptera*. Members of the order *Fleas* include, but are not limited to, *Ctenocephatides canis* and *Ctenocephatides canis*. Members of the order *Diptera* include, but are not limited to, species of the genus *Fly*; *Dermatophytes*, such as *Hippophae rhamnoides* and *Hemiptera*; *Bungarus*, such as *Bungarus* and *Bungarus*; *Bungarus*; *Bungarus*; midges; and mosquitoes. Members of the order Tetranychida include, but are not limited to, blood-sucking lice and chewing lice, such as the woolly lice (Bovicola ovvis) and the cow lice.

[0215] When used in the context of parasites inside or outside an animal, the term "effective amount" refers to the amount or dose of the compound of the present invention or a salt thereof, which, when administered to an animal in a single or multiple doses, provides the desired effect inside or outside the animal. An attending diagnostic expert (as a person skilled in the art) can readily determine the effective amount by using known techniques and by observing results obtained under similar conditions. In determining the effective amount, the attending diagnostic expert considers a number of factors, including but not limited to: the species of the mammal; its size, age, and general health status; the parasite to be controlled and the extent of infection; the specific disease or condition involved; the extent or severity of the disease or condition; the individual response; the specific compound administered; the administration pattern; the bioavailability characteristics of the administered formulation; the selected dosage regimen; the use of concomitant drugs; and other relevant factors.

[0216] The compounds of the present invention can be administered to animals by any route with the desired effect, including but not limited to topical, oral, parenteral, and subcutaneous administration. Topical administration is preferred. Formulations suitable for topical administration include, for example, solutions, emulsions, and suspensions, and can be in the form of pouring, dotting, spraying, spray race, or dipping. Alternatively, the compounds of the present invention can be administered by ear tag or collar.

[0217] The salt forms of the compounds of the present invention include both pharmaceutically acceptable and veterinary acceptable salts, which may differ from those chemically acceptable for agricultural use. Pharmaceutically and veterinary acceptable salts and common methods for preparing them are well known in the art. See, for example, Gould, PL, "Salt selection for basic drugs", International Journal of Pharmaceutics, 33: 201-217 (1986); Bastin, RJ et al., "Salt Selection and Optimization Procedures for Pharmaceutical New Chemical Entities", Organic Process Research and Development, 4: 427-435 (2000); and Berge, SM et al., "Pharmaceutical Salts", Journal of Pharmaceutical Sciences, 66: 1-19, (1977). Those skilled in the art of synthesis will understand that, using techniques and conditions well known to those of ordinary skill in the art, the compounds of the present invention can be readily converted into salts and can be separated as salts (such as hydrochlorides). Furthermore, those skilled in the art of synthesis will understand that the compounds of the present invention can be readily converted into the corresponding free bases and can be separated from the corresponding salts as the corresponding free bases.

[0218] The present invention also provides a method for controlling pests such as mosquitoes and other disease vectors; see also http: / / www.who.int / malaria / vector_control / irs / en / . In one embodiment, the method for controlling pests includes applying the composition of the invention to the target pests, their location, or a surface or substrate by brushing, rolling, spraying, sprinkling, or impregnation. By way of example, the method of the present invention is contemplated for application of IRS (Indoor Residual Spray) to surfaces such as walls, ceilings, or floor surfaces. In another embodiment, the application of such compositions to substrates, such as nonwoven or woven materials, in the form of mesh fabrics, covers, bedding, curtains, and tents (or materials that can be used in the manufacture of these articles), is contemplated.

[0219] In one embodiment, a method for controlling such pests includes applying a biocidally effective amount of the composition of the invention to the target pests, to their location, or to a surface or substrate to provide effective residual biocidal activity on the surface or substrate. This application can be carried out by brushing, rolling, spraying, sprinkling, or impregnating the biocidal composition of the invention. By way of example, the method of the invention is considered for IRS application to surfaces (such as wall, ceiling, or floor surfaces) to provide effective residual biocidal activity on the surface. In another embodiment, the application of such a composition for residual control of pests on a substrate, such as a fabric material (or potentially used in the manufacture of these articles) in the form of netting, coverings, bedding, curtains, and tents, is considered.

[0220] The substrate to be treated (including nonwovens, fabrics, or meshes) can be made of natural fibers such as cotton, raffia leaf fibers, jute, flax, sisal, burlap, or wool, or synthetic fibers such as polyamide, polyester, polypropylene, polyacrylonitrile, etc. Polyester is particularly suitable. Methods for treating textiles are known, for example, WO 2008 / 151984, WO 2003 / 034823, US 5631072, WO 2005 / 64072, WO 2006 / 128870, EP 1724392, WO 2005113886, or WO2007 / 090739.

[0221] Another area of ​​application for the compositions according to the invention is in the field of tree injection / trunk treatment for all ornamental trees as well as all kinds of fruit and nut trees.

[0222] In the field of tree injection / trunk treatment, the compounds according to the present invention are particularly suitable for combating wood-boring insects from the Lepidoptera and Coleoptera mentioned above, especially those listed in Tables A and B below:

[0223] Table A. Examples of economically important invasive wood-boring insects.

[0224]

[0225] Table B. Examples of local wood-boring insects of economic importance.

[0226]

[0227] This invention can also be used to control any insect pests that can exist in lawn grass, including, for example, beetles, caterpillars, fire ants, ground pearls, millipedes, sowbugs, mites, mole crickets, scale insects, mealybugs, ticks, froghoppers, southern wheat bugs, and grubs. This invention can be used to control insect pests at all stages of their life cycle, including eggs, larvae, nymphs, and adults.

[0228] Specifically, this invention can be used to control insect pests that feed on the roots of lawn grasses, including grubs (such as Cyclocephala spp., e.g., the marked scarab beetle, C. lurida), Rhizotrogus (e.g., the European scarab beetle, R. majalis), Cotinus (e.g., the green June beetle, C. nitida), Popillia spp. (e.g., the Japanese beetle, P. japonica), Phyllophoraga spp. (e.g., the May / June beetle), Ataenius (e.g., the Black turfgrass ataenius, A. spretulus), Malladeras spp. (e.g., the Asiatic garden beetle, M. castanea and Tomarus), ground pearl (Margarodes spp.), mole crickets (brownish-yellow, southern, and short-winged; Scapteriscus spp., Gryllotalpa africana) and leatherjackets (European crane fly, Tipula spp.)).

[0229] This invention can also be used to control insect pests in lawn grasses of thatched houses, including armyworms (such as the fall armyworm and the common armyworm Pseudaletia unipuncta), root cutters, weevils (species of the genus Sphenophorus, such as S. venatusverstitus and S. parvulus), and grass moths (such as species of the genus Crambus and the tropical grass moth Herpetogramma phaeopteralis).

[0230] This invention can also be used to control insect pests in turfgrass that live on the ground and feed on the leaves of turfgrass. These insect pests include wheat bugs (such as southern wheat bugs and southern stem bugs (Blissus insularis)), bermudagrass mite (Eriophyes cynodoniensis), grass mealybug (Antonina graminis)), two-lined grasshopper (Propsapia bicincta), leafhoppers, root-cutting moths (Noctuidae), and wheat aphids.

[0231] This invention can also be used to control other harmful organisms in lawn grass, such as introduced red imported fire ants (Solenopsis invicta) that create nests in lawns.

[0232] In the field of hygiene, the compositions according to the invention are effective against ectoparasites such as hard ticks, soft ticks, scabies mites, fall mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.

[0233] Examples of this type of parasite are:

[0234] Lice: Species of the genera *Linognathus*, *Linognathus*, *Phtirus*, and *Phtirus*.

[0235] Trichophagia: Species of the genera *Hymenopteris*, *Hymenopteris*, *Hymenopteris*, *Hymenopteris*, *Hymenopteris*, *Hymenopteris*, *Hymenopteris*, *Hymenopteris*, *Hymenopteris*, *Hymenopteris*, and *Hymenopteris*.

[0236] Diptera and the suborders Nematocerina and Brachycerina, such as species of the genera *Aedes*, *Anopheles*, *Culex*, *Simulium*, *Eusimulium*, *Phlebotomus*, *Lutzomyia*, *Culicoides*, *Chrysops*, *Hybomitra*, *Atylotus*, *Tabanus*, *Haematopota*, and *Philipomyia*. spp.), species of the genera *Braulaspp.*, *Musca spp.*, *Hydrotaea spp.*, *Haematobia spp.*, *Morellia spp.*, *Fannia spp.*, *Glossina spp.*, *Calliphora spp.*, *Lucilia spp.*, *Chrysomyia spp.*, *Wohlfahrtia spp.*, *Sarcophagas spp.*, *Oestrus spp.*, *Hypoderma spp.*, *Gasterophilus spp.*, *Hippobosca spp.*, and *Lipoptena*. spp.) and species of the genus Melophagos (Melophagus spp.).

[0237] Siphonapterida, including species of the genera *Pulex*, *Xenopsylla*, and *Xenopsylla*.

[0238] Heteropterida, including species of the genera *Pycnodon*, *Triatomine*, *Aspergillus*, and *Panstrongylus* spp.

[0239] Blattodea, including species such as the Oriental cockroach (Blatta orientalis), the American cockroach (Periplaneta americana), the German cockroach (Blattelagermanica), and species of the genus Supella (Supella spp.).

[0240] Acaria (subclass Acaria, family Acarida), and the orders Meta-stigmata and Meso-stigmata, including species of the genera *Argas*, *Ornithodorus*, *Otobius*, *Ixodes*, *Amblyommas*, *Boophilus*, *Dermacentor*, *Haemophysalis*, *Hyalomma*, *Rhipicephalus*, *Dermanyssus*, *Raillietia*, and *Pneumonyssus*. spp.), species of the genus *Sternostoma* spp., and species of the genus *Varroaspp.*.

[0241] Actinedida (prostigmata) and Acaridida (Astigmata), including species of the genera *Acarapis*, *Cheyletiella*, *Ornithocheyletia*, *Myobia*, *Psorergates*, *Demodex*, *Trombicula*, *Listrophorus*, *Acarus*, *Tyrophagus*, *Caloglyphus*, *Hypodectes*, and *Pterolichus*. Species of the genera *Psoroptes*, *Chorioptes*, *Otodectes*, *Sarcoptes*, *Notoedress*, *Knemidocoptes*, *Cytodites*, and *Laminosioptes*.

[0242] The compositions according to the invention are also suitable for protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and cards, leather, flooring and buildings from insect infestation.

[0243] The compositions according to the invention can be used, for example, to combat the following pests: beetles, such as the North American house longhorn beetle, long-haired longhorn beetle, furniture borer, red-haired borer, comb-horned vein borer, pine longhorn beetle (Dendrobium pertinex), pine bud twig borer, carpini beetle, brown powdery beetle, African powdery beetle, southern powdery beetle, oak powdery beetle, pubescent powdery beetle, breast powdery beetle, scale powdery beetle, species of the genus *Bark beetle*, species of the genus *Bark beetle*, coffee black longhorn beetle, oak longhorn beetle, brown heteroptera longhorn beetle, *Bacillus longhorn beetle*, and bamboo longhorn beetle; and also hymenoptera, such as the blue-black tree beetle, spruce tree beetle, thiaga tree beetle, and tree beetle (Urocerus augur); and termites, such as the European wood termite (Kalotermes). *Flavocortis flavicollis*, *Reticulitermes simonii*, *Reticulitermes sanctus*, *Reticulitermes cerana*, *Reticulitermes cerana*, *Reticulitermes cerana*, *Reticulitermes cerana*, *Reticulitermes cerana*, *Reticulitermes cerana*, *Reticulitermes neriifolius*, and *Reticulitermes neriifolius*; and borers, such as silverfish. Compounds having Formula I, or salts thereof, are particularly suitable for controlling one or more pests selected from the following families: Noctuidae, Pyrenidae, Chrysophagidae, Thripsidae, Stink bugs, Toxascaridae, Planthoppers, Aphids, Noctuidae, Pyralidae, Root-knot nematodes, and Heterodermidae. In a preferred embodiment of each aspect, compound TX (wherein the abbreviation "TX" means "a compound selected from the compounds defined in Tables 1 to 4 and Tables P1 to P2") controls one or more pests selected from the following families: Noctuidae, Pyrenidae, Chrysophagidae, Thripsidae, Stink bugs, Toxascaridae, Planthoppers, Aphids, Noctuidae, Pyralidae, Root-knot nematodes, and Heterodermidae.

[0244] Compounds having Formula I or salts thereof are particularly suitable for controlling one or more pests selected from the genera *Gnaphalium*, *Plutella*, *Thrips*, *Plutella*, *Cydia*, *Rhizoctonia*, *Aphidius*, *Aphidius*, *Leymus*, *Aphidius*, *Leymus*, *Aphidius*, *Leptochloa*, *Leptochloa*, and *Potentilla*. In a preferred embodiment of each aspect, compound TX (wherein the abbreviation "TX" means "a compound selected from the compounds defined in Tables 1 to 4 and Tables P1 to P2") controls one or more pests selected from the genera *Gnaphalium*, *Plutella*, *Thrips*, *Plutella*, *Cydia*, *Leptochloa*, *Aphidius*, *Aphidius*, *Leymus*, *Aphidius*, *Leptochloa*, and *Potentilla*.

[0245] Compounds having formula I or salts thereof are particularly suitable for controlling one or more of the following: sea grebe moth, diamondback moth, western flower thrips, tobacco thrips, hero American bug, codling moth, brown rice leafhopper, peach aphid, soybean looper, soybean aphid, cucumber leaf beetle, cereal constrictor aphid, and rice stem borer.

[0246] In preferred embodiments of each aspect, compound TX (where the abbreviation "TX" means "a compound selected from the compounds defined in Tables 1 to 4 and Tables P1 to P2") controls one or more of the following: sea worm, diamondback moth, western flower thrips, tobacco thrips, American stink bug, codling moth, brown rice leafhopper, peach aphid, soybean looper, soybean aphid, cucumber leaf beetle, cereal constrictor aphid, and rice stem borer, such as sea worm + TX, diamondback moth + TX; western flower thrips + TX, tobacco thrips + TX, American stink bug + TX, codling moth + TX, brown rice leaf beetle + TX, peach aphid + TX, soybean looper + TX, soybean aphid + TX, cucumber leaf beetle + TX, cereal constrictor aphid + TX, and rice stem borer + TX.

[0247] In each embodiment, a compound from Tables 1 to 4 and Tables P1 to P2 is suitable for controlling the following pests on cotton, vegetables, corn, cereals, rice, and soybean crops: sea grebe moth, diamondback moth, western flower thrips, tobacco thrips, hero American bug, codling moth, brown rice leafhopper, peach aphid, soybean looper, soybean aphid, cucumber leaf beetle, cereal constrictor aphid, and rice stem borer.

[0248] In the embodiments, one compound from Tables 1 to 4 and Tables P1 to P2 is suitable for controlling the cabbage looper (Mamestra) (preferably on vegetables), the codling moth (preferably on apples), the small green leafhopper (Empoasca) (preferably on vegetables and vineyards), the potato leaf beetle (Leptinotarsa) (preferably on potatoes), and the rice stem borer (preferably on rice).

[0249] Compounds according to the invention can have any number of benefits, particularly including favorable levels of bioactivity for protecting plants against insects or superior properties for use as active ingredients in agrochemicals (e.g., higher bioactivity, favorable activity spectrum, increased safety (against non-target organisms such as fish, birds, and bees), improved physicochemical properties, or increased biodegradability). In particular, it has been unexpectedly found that certain compounds having formula (I) can exhibit favorable safety relative to non-target arthropods, especially pollinators (such as honeybees, solitary bees, and bumblebees). Most particularly, relative to the Italian bee (Apis mellifera).

[0250] The compounds according to the invention can be used as pest control agents in their unmodified form, but they are generally formulated into compositions in a variety of ways using formulation aids such as carriers, solvents, and surfactants. These formulations can be in various physical forms, for example, as dusts, gels, wettable powders, water-dispersible granules, water-dispersible tablets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, flowable oils, aqueous dispersions, oily dispersions, suspensions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as a carrier), impregnated polymer films, or in other known forms, such as those described in the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, 1st Edition, Second Revision (2010). Such formulations can be used directly or diluted before use. It can be diluted with, for example, water, liquid fertilizer, micronutrients, biological organisms, oil or solvents.

[0251] These formulations can be prepared, for example, by mixing the active ingredients with formulation aids to obtain compositions in the form of finely dispersed solids, particles, solutions, dispersions, or emulsions. These active ingredients can also be formulated with other aids, such as finely dispersed solids, mineral oils, oils of plant or animal origin, modified oils of plant or animal origin, organic solvents, water, surfactants, or combinations thereof.

[0252] These active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredient within a porous carrier. This allows the active ingredient to be released into the environment in a controlled amount (e.g., slow release). Microcapsules typically have a diameter of 0.1 to 500 micrometers. They contain an amount of active ingredient that is approximately 25% to 95% by weight of the capsule. These active ingredients can be in the form of a monolithic solid, fine particles in a solid or liquid dispersion, or in a solution-suitable form. The encapsulating membrane can contain, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, or chemically modified polymers, as well as starch xanthates, or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely dispersed particles within a solid matrix of the base material, but these microcapsules themselves are not encapsulated.

[0253] Suitable formulation aids for preparing compositions according to the invention are known in themselves. As liquid carriers, the following can be used: water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosinate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N Dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol ether, 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, glyceryl acetate, glyceryl diacetate, triacetic acid Glyceryl esters, hexadecane, hexanediol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, isopropylidene acetone, methoxypropanol, methyl isopentyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleyleneamine, o-xylene, phenol, polyethylene glycol, propionic acid, lactic acid Propylene acetate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin wax, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols with higher molecular weights, such as pentanol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.

[0254] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin, and similar substances.

[0255] Many surfactants can be advantageously used in both solid and liquid formulations, particularly those that can be diluted with a carrier before use. Surfactants can be anionic, cationic, nonionic, or polymeric, and they can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include, for example, salts of alkyl sulfates, such as diethanolammonium dodecyl sulfate; salts of alkyl aryl sulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / olefin oxide addition products, such as ethoxylated nonylphenol; alcohol / olefin oxide addition products, such as ethoxylated tridecyl alcohol; soaps, such as sodium stearate; salts of alkyl naphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate; salts of dialkyl sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary ammonium, such as dodecyltrimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of monoalkyl and dialkyl phosphate esters; and other substances, such as those described in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing. Corp.), Ridgewood, New Jersey (1981).

[0256] Other adjuvants that can be used in formulations for killing harmful organisms include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, substances that neutralize or change pH and buffer solutions, corrosion inhibitors, fragrances, humectants, absorption enhancers, micronutrients, plasticizers, flow aids, lubricants, dispersants, thickeners, antifreeze agents, microbial agents, and liquid and solid fertilizers.

[0257] The compositions according to the invention may include additives comprising oils of plant or animal origin, mineral oils, alkyl esters of such oils, or mixtures of such oils with oil derivatives. The amount of oil additive in the compositions according to the invention is typically 0.01% to 10% of the mixture to be applied. For example, the oil additive may be added to the spray can at the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oils or plant-derived oils, such as rapeseed oil, olive oil, or sunflower oil; emulsified vegetable oils; alkyl esters of plant-derived oils, such as methyl derivatives; or animal-derived oils, such as fish oil or tallow. Preferred oil additives include C8-C... 22 Alkyl esters of fatty acids, especially C 12 -C 18Methyl derivatives of fatty acids, such as methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are known in the Compendium of Herbicide Adjuvants, 10th edition, Southern Illinois University, 2010.

[0258] The compositions of the present invention typically comprise 0.1% to 99%, particularly 0.1% to 95% by weight, of the compound of the present invention and 1% to 99.9% by weight, of formulation aids, which preferably comprise 0 to 25% by weight of a surfactant. Commercial products may preferably be formulated as concentrates, while end users will typically use diluted formulations.

[0259] Application rates vary widely and depend on soil properties, application method, crop, pests to be controlled, primary climatic conditions, and other factors governed by application method, application time, and target crop. Generally, compounds can be applied at rates from 1 l / ha to 2000 l / ha, especially from 10 l / ha to 1000 l / ha.

[0260] Preferred formulations may have the following composition (by weight%):

[0261] Emulsifiable concentrate :

[0262] Active ingredient: 1% to 95%, preferably 60% to 90%

[0263] Surfactant: 1% to 30%, preferably 5% to 20%

[0264] Liquid carrier: 1% to 80%, preferably 1% to 35%

[0265] Dust powder :

[0266] Active ingredient: 0.1% to 10%, preferably 0.1% to 5%.

[0267] Solid carrier: 99.9% to 90%, preferably 99.9% to 99%.

[0268] Suspension concentrate:

[0269] Active ingredient: 5% to 75%, preferably 10% to 50%

[0270] Water: 94% to 24%, preferably 88% to 30%

[0271] Surfactant: 1% to 40%, preferably 2% to 30%

[0272] wettable powder :

[0273] Active ingredient: 0.5% to 90%, preferably 1% to 80%

[0274] Surfactant: 0.5% to 20%, preferably 1% to 15%

[0275] Solid carrier: 5% to 95%, preferably 15% to 90%

[0276] Granules:

[0277] Active ingredient: 0.1% to 30%, preferably 0.1% to 15%

[0278] Solid carrier: 99.5% to 70%, preferably 97% to 85%

[0279] The following examples further illustrate (but do not limit) the invention.

[0280]

[0281] The combination is thoroughly mixed with these adjuvants and the mixture is thoroughly ground in a suitable grinder to obtain a wettable powder that can be diluted with water to give a suspension of the desired concentration.

[0282]

[0283] The combination is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable grinder to obtain a powder that can be used directly for seed treatment.

[0284]

[0285] Emulsions with any required dilution that can be used in plant protection can be obtained by diluting such concentrates with water.

[0286]

[0287] A ready-to-use dust powder is obtained by mixing the mixture with a carrier and grinding the mixture in a suitable grinder. Such a powder can also be used for dry seed dressing.

[0288]

[0289] The mixture is combined with these additives and ground, and then the mixture is moistened with water. The mixture is extruded and then dried in an air stream.

[0290]

[0291] The finely ground mixture is then uniformly applied in a mixer to kaolin moistened with polyethylene glycol. This process yields dust-free coated particles.

[0292] suspension concentrate

[0293]

[0294] The finely ground mixture is tightly mixed with an auxiliary agent to obtain a suspension concentrate, from which a suspension concentrate can be diluted with water to obtain a suspension of any desired dilution. Using such a dilution, living plants along with their propagation material can be treated and protected against microbial infections by spraying, watering, or immersion.

[0295] Flowable concentrate for seed treatment

[0296]

[0297] The finely ground mixture is tightly mixed with an auxiliary agent to obtain a suspension concentrate, from which a suspension concentrate can be diluted with water to obtain a suspension of any desired dilution. Using such a dilution, living plants along with their propagation material can be treated and protected against microbial infections by spraying, watering, or immersion.

[0298] Sustained-release capsule suspension

[0299] 28 parts of the mixture were combined with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture was emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of an antifoaming agent, and 51.6 parts of water until the desired particle size was achieved. 2.8 parts of a 1,6-hexanediamine mixture in 5.3 parts of water were added to this emulsion. The mixture was stirred until polymerization was complete. The resulting capsule suspension was stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. This capsule suspension formulation contained 28% of the active ingredient. The diameter of the medium capsules was 8-15 micrometers. The resulting formulation was applied to seeds as an aqueous suspension suitable for this purpose.

[0300] Formulation types include emulsion concentrates (EC), suspension concentrates (SC), suspension emulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), oil dispersions (OD), oil suspensions (OF), oil-soluble liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical grade (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG), or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0301] Preparation example:

[0302] LCMS method:

[0303] Method 1:

[0304] Spectra were recorded on a Waters mass spectrometer (SQD, SQDII, or QDA single quadrupole mass spectrometer) equipped with an electro-ejector source (polarity: positive and negative ions), capillary voltage: 0.8–3.00 kV, cone voltage: 5–30 V, source temperature: 120–150°C, desolvation temperature: 350–600°C, cone gas flow rate: 50–150 l / h, desolvation gas flow rate: 650–1000 l / h, mass range: 110–950 Da, and a Waters Acquity UPLC: binary pump, heated column chamber, diode array detector, and ELSD. Column: Waters UPLC HSS T3, 1.8 µm, 30 x 2.1 mm, temperature: 60°C, DAD wavelength range (nm): 210 to 400, run time: 1.5 min; solvent: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; flow rate (ml / min): 0.85, gradient: 10% B isocratic for 0.2 min, then 10%-100% B, 100% B isocratic for 0.2 min over 1.0 min, then 100%-10% B, 10% B isocratic for 0.05 min over 0.05 min.

[0305] Method 2 :

[0306] Spectra were recorded on a mass spectrometer (SQD2 or QDA single quadrupole mass spectrometer) from Waters Corporation, equipped with an electro-jet source (polarity: positive and negative polarity switching), capillary voltage: 0.8–3.00 kV, cone range: 25, source temperature: 120°C–150°C, desolvation temperature: 500°C–600°C, cone gas flow rate: 50 L / h, desolvation gas flow rate: 1000 L / h, mass range: 110–850 Da) and an Acquity UPLC from Waters Corporation: quaternary solvent manager, heated column chamber, 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 to 400, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.05% HCOOH; gradient: 0 min 10% B; 0. min-0.2 min 10%-50% B; 0.2-0.6 min 50%-100% B; 0.6 min-1.3 min 100% B; 1.3 min-1.4 min 100%-10% B; 1.4 min-1.6 min 10% B; flow rate (mL / min): 0.6.

[0307] Method 3:

[0308] Spectra were recorded on an ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) from Waters Corporation, which is equipped with an electro-ejector source (polarity: positive or negative ion, capillary: 3.0 kV, cone: 30 V, extractor: 3.00 V, source temperature: 150°C, desolvation temperature: 400°C, cone gas flow rate: 60 L / hr, desolvation gas flow rate: 700 L / hr, mass range: 140 to 800 Da) and an ACQUITY UPLC from Waters Corporation, which has a solvent degassing device, a binary pump, a heated column chamber, and a diode array detector. Column: Waters UPLC HSS T3, 1.8 µm, 30 x 2.1 mm, temperature: 60°C, DAD wavelength range (nm): 210 to 400, solvent gradient: A = water / methanol 9:1 + 0.1% formic acid, B = acetonitrile + 0.1% formic acid, gradient: 0%-100% B, over 2.5 min; flow rate (ml / min): 0.75.

[0309] The following abbreviations are used in the experimental description below: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, RT = retention time, min = minutes.

[0310] Example P1: 4-[5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine- 3-Carbonyl]-N-ethyl-piperazine-1-sulfonamide (compound P1.1):

[0311]

[0312] Step 1: Ethyl 5-cyano-6-hydroxy-2-(trifluoromethyl)pyridine-3-carboxylate

[0313]

[0314] A solution of sodium ethoxide (1.1 equivalents) in ethanol (20% w / w) was slowly added to a suspension of 2-cyanoacetamide (5.9 g, 70.2 mmol, 1 equivalent) at 4°C, and the mixture was stirred for 15 minutes. Then, a solution of ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxo-butyrate (17 g, 70.1 mmol) in 34 ml of ethanol was added under ice-cooling. The reaction mixture was stirred for 16 hours and allowed to reach room temperature. The reaction mixture was then poured into an ice-cold 1 N hydrochloric acid solution. The resulting mixture was diluted with ice-cold water and stirred for 20 minutes. The precipitate was filtered, washed twice with ice-cold water, and dried. 12.4 g of ethyl 5-cyano-6-hydroxy-2-(trifluoromethyl)pyridine-3-carboxylate was obtained, with a purity greater than 95% as determined by quantitative NMR. 1 ¹H-NMR [ppm] in CDCl₃: 1.29 (t, 3H), 4.29 (q, 2H), 8.27 (s, 1H).

[0315] Step 2: 4-(Ethylaminosulfonyl)piperazine-1-carboxylic acid tert-butyl ester

[0316]

[0317] Piperazine-1-carboxylate tert-butyl ester (2.00 g, 10.7 mmol) was dissolved in DCM (43 mL), and pyridine (1.31 mL, 16.1 mmol, 1.5 equivalents) was added under nitrogen atmosphere, followed by the addition of thioyl chloride (1.01 mL, 12.9 mmol, 1.2 equivalents). The mixture was stirred at room temperature for 16 hours. Then 1N HCl was added and the mixture was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered, and concentrated under vacuum. The residue consisting of 4-chlorosulfonylpiperazine-1-carboxylate tert-butyl ester (2 g, 7.02 mmol) was dissolved in DCM (14 mL). Triethylamine (1.97 mL, 14.04 mmol, 2 equivalents), 4-dimethylaminopyridine (172 mg, 0.18 mL, 1.40 mmol, 0.2 equivalents), and ethylamine (14.04 mmol, 7 mL of a 2.0 mol / L solution in THF) were added. The reaction mixture was stirred at room temperature for 16 hours. Then 1N HCl was added and the mixture was extracted twice with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under vacuum to give 2.20 g of tert-butyl 4-(ethylaminosulfonyl)piperazine-1-carboxylate. 1 H-NMR [ppm] in CDCl3: 1.17 (t, 3 H), 1.45 (s, 9 H), 3.09 (quintet, 2 H), 3.12–3.17 (m, 4 H), 3.45–3.50 (m, 4 H), 4.57 (t, 1 H).

[0318] Step 3: N-ethylpiperazine-4-onthium-1-sulfonamide chloride

[0319]

[0320] Hydrogen chloride (35 mL, 4 mol / L solution in 1,4-dioxane) was added to a solution of tert-butyl 4-(ethylaminosulfonyl)piperazine-1-carboxylate (3.50 g, 12.0 mmol) in methanol (35 mL). The reaction mixture was stirred at room temperature for 16 hours and then evaporated to dryness. The residue was washed with n-pentane, followed by ethyl acetate and dried under vacuum to give 2.5 g of N-ethylpiperazine-4-onthium-1-sulfonamide chloride. 1¹H-NMR [ppm] in DMSO-d6: 1.06 (t, 3 H), 2.93 (quintet, 2 H), 3.05–3.18 (m, 4 H), 3.23–3.32 (m, 4 H), 7.45–7.53 (m, 1 H), 9.48 (broad s, 2 H).

[0321] Step 4: Ethyl 5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine-3-carboxylate

[0322]

[0323] Potassium carbonate (4.88 g, 34.6 mmol, 3 equivalents) and sodium iodide (364 mg, 2.31 mmol, 0.2 equivalents) were added to a solution of ethyl 5-cyano-6-hydroxy-2-(trifluoromethyl)pyridine-3-carboxylate (3.00 g, 11.5 mmol) in acetone (58 mL), followed by the addition of 2-(bromomethyl)-1-fluoro-4-(trifluoromethyl)benzene (4.45 g, 2.71 mL, 17.3 mmol, 1.5 equivalents). The reaction mixture was stirred at 70°C for 3 hours. The suspension was filtered, washed with acetone, and dried under vacuum. The residue was purified by combiflash to give 4.55 g of ethyl 5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine-3-carboxylate. 1 ¹H-NMR [ppm], in CDCl₃: 1.39 (t, 3H), 4.45 (q, 2H), 5.70 (s, 2H), 7.22–7.29 (m, 1H), 7.64–7.72 (m, 1H), 7.89–7.94 (m, 1H), 8.42 (s, 1H). LC-MS (Method 1): RT = 1.21 min; [M+H] + = 437.

[0324] Step 5: 5-Cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine-3-carboxylic acid

[0325]

[0326] Ethyl 5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine-3-carboxylic acid (4.50 g, 10.3 mmol) was dissolved in THF (26 mL) and water (12 mL), and lithium hydroxide monohydrate (1.01 g, 41.3 mmol, 4 equivalents) was added at room temperature. The reaction mixture was stirred at room temperature until the starting material disappeared on TLC. The reaction mixture was then diluted with ethyl acetate and 2N hydrochloric acid. The mixture was extracted three times with ethyl acetate. The combined organic phases were washed twice with water and once with brine, dried over sodium sulfate, filtered, and concentrated under vacuum. After milling with a small amount of DCM, 1.63 g of 5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine-3-carboxylic acid was obtained. ¹H-NMR [ppm] in DMSO-d6: 5.68 (s, 2H), 7.54 (t, 1H), 7.83–7.89 (m, 1H), 8.05–8.11 (m, 1H), 8.83 (s, 1H), 14.16 (wide s, 1H). LC-MS (Method 1): RT = 1.04 min; [M+H]+ = 409.

[0327] Step 6: 4-[5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine-3-carbonyl]-N-ethyl-piperazine-1-sulfonamide (compound P1.1)

[0328]

[0329] To a solution of 5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine-3-carboxylic acid (180 mg, 0.441 mmol) in ethyl acetate (6.6 mL), N-ethylpiperazine-1-sulfonamide (128 mg, 0.661 mmol, 1.5 equivalents) was added, followed by propanephosphonic anhydride (T3P, 505 mg, 0.473 mL, 0.794 mmol, 1.8 equivalents; 50% solution in ethyl acetate) and N,N-diisopropylethylamine (228 mg, 0.307 mL, 1.76 mmol, 4.0 equivalents). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into an aqueous solution of NaHCO3. The mixture was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by combiflash. 180 mg of 4-[5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine-3-carbonyl]-N-ethyl-piperazine-1-sulfonamide was obtained as a white foam. 1 ¹H-NMR [ppm] in CDCl₃: 1.24 (t, 3H), 3.16 (quintet, 2H), 3.11–3.43 (m, 6H), 3.74–3.87 (m, 1H), 3.93–4.04 (m, 1H), 4.08 (t, 1H), 5.62–5.73 (m, 2H), 7.22–7.29 (m, 1H), 7.64–7.72 (m, 1H), 7.88–7.94 (m, 1H), 7.98 (s, 1H). LC-MS (Method 1): RT = 1.07 min; [M+H] + = 584.

[0330] Example P2: 4-[5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine- 3-Carbonyl]-N-ethyl-N-methyl-piperazine-1-sulfonamide (compound P1.2):

[0331]

[0332] To a solution of 5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine-3-carboxylic acid (200 mg, 0.490 mmol) in ethyl acetate (7.4 mL), N-ethyl-N-methyl-piperazine-1-sulfonamide (152 mg, 0.735 mmol, 1.5 equivalents) was added, followed by propanephosphonic anhydride (T3P, 561 mg, 0.523 mL, 0.882 mmol, 1.8 equivalents; 50% solution in ethyl acetate) and N,N-diisopropylethylamine (253 mg, 0.341 mL, 1.96 mmol, 4.0 equivalents). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into an aqueous solution of NaHCO3. The mixture was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by combiflash. 230 mg of 4-[5-cyano-6-[[2-fluoro-5-(trifluoromethyl)phenyl]methoxy]-2-(trifluoromethyl)pyridine-3-carbonyl]-N-ethyl-N-methyl-piperazine-1-sulfonamide was obtained as a white foam. 1 ¹H-NMR [ppm] in CDCl₃: 1.21 (t, 3H), 2.86 (s, 3H), 3.12–3.40 (m, 8H), 3.74–3.86 (m, 1H), 3.90–3.99 (m, 1H), 5.63–5.73 (m, 2H), 7.22–7.29 (m, 1H), 7.63–7.72 (m, 1H), 7.88–7.94 (m, 1H), 7.96 (s, 1H). LC-MS (Method 1): RT = 1.12 min; [M+H] + = 598.

[0333] Example P3: 4-[5-cyano-6-[(2,2-difluoro-1,3-benzodioxane-5-yl)methoxy]-2- [(difluoromethyl)pyridine-3-carbonyl]-N-ethyl-piperazine-1-sulfonamide (compound P1.3):

[0334]

[0335] Step 1: Ethyl 5-cyano-6-[(2,2-difluoro-1,3-benzodioxane-5-yl)methoxy]-2-(difluoromethyl)pyridine-3-carboxylate

[0336]

[0337] Ethyl 5-cyano-2-(difluoromethyl)-6-hydroxy-pyridine-3-carboxylate (5.0 g, 20.6 mmol) was synthesized as described in patent application WO 2017195703 of Ruzoda Co., Ltd. Potassium carbonate (8.5 g, 61.8 mmol, 3 equivalents) and 5-(chloromethyl)-2,2-difluoro-1,3-benzodioxane (5.4 g, 25 mmol, 1.2 equivalents) were added to a solution of DMF (52 mL). The mixture was stirred at 60°C for 3 hours. Water (30 mL) was then added, and the mixture was extracted with ethyl acetate (2 × 20 mL). The organic layers were combined, washed with brine (20 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified using combiflash (40%-50% ethyl acetate / cyclohexane) to give 3.8 g of ethyl 5-cyano-6-[(2,2-difluoro-1,3-benzodioxane-5-yl)methoxy]-2-(difluoromethyl)pyridine-3-carboxylate. 1 H-NMR 400 MHz, in CDCl3 [ppm]: 1.44 (t, 3H), 4.45 (q, 2H), 5.63 (s, 2H), 7.08 (d, 1H), 7.30 (d, 1H), 7.34 (s, 1H), 7.52 (t, 1H), 8.59 (s, 1H).

[0338] Step 2: 5-Cyano-6-[(2,2-difluoro-1,3-benzodioxane-5-yl)methoxy]-2-(difluoromethyl)pyridine-3-carboxylic acid

[0339]

[0340] Ethyl 5-cyano-6-[(2,2-difluoro-1,3-benzodioxane-5-yl)methoxy]-2-(difluoromethyl)pyridine-3-carboxylic acid (3.8 g, 9.2 mmol) was dissolved in 1,4-dioxane (17 mL) and water (14 mL). Lithium hydroxide hydrate (0.55 g, 23 mmol, 2.5 equivalents) was then added, and the mixture was stirred at room temperature for 6 hours. Dilute hydrochloric acid was then added, and a precipitate formed upon cooling. The precipitate was filtered, washed with cold water, and dissolved in ethyl acetate. The solution was dried over sodium sulfate, filtered, and concentrated under vacuum to give 3.5 g of 5-cyano-6-[(2,2-difluoro-1,3-benzodioxane-5-yl)methoxy]-2-(difluoromethyl)pyridine-3-carboxylic acid. 1H-NMR 400 MHz, in DMSO-d6 [ppm]: 5.58 (s, 2H), 7.34–7.47 (m, 2H), 7.55 (t, 1H), 7.58 (s, 1H), 8.80 (s, 1H), 13.73–14.69 (wide s, 1H).

[0341] Step 3: 4-[5-cyano-6-[(2,2-difluoro-1,3-benzodioxane-5-yl)methoxy]-2-(difluoromethyl)pyridine-3-carbonyl]-N-ethyl-piperazine-1-sulfonamide (compound P1.3):

[0342]

[0343] The mixture of 5-cyano-6-[(2,2-difluoro-1,3-benzodioxane-5-yl)methoxy]-2-(difluoromethyl)pyridine-3-carboxylic acid (250 mg, 0.651 mmol) in ethyl acetate (5.2 mL) was treated with N,N-diisopropylethylamine (0.33 mL, 1.95 mmol, 3.0 equivalents), N-ethylpiperazine-4-onthium-1-sulfonamide chloride (209 mg, 0.911 mmol, 1.4 equivalents), and propanephosphonic anhydride (T3P, 1.24 g, 1.16 mL, 1.95 mmol, 3 equivalents; 50% solution in ethyl acetate). The resulting pale yellow solution was stirred at room temperature for 3 hours. Water was added to the reaction mixture. The mixture was extracted three times with ethyl acetate. The combined organic layers were washed with saturated potassium carbonate solution (10 mL) and brine (10 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by reversed-phase chromatography to give 150 mg of 4-[5-cyano-6-[(2,2-difluoro-1,3-benzodioxane-5-yl)methoxy]-2-(difluoromethyl)pyridine-3-carbonyl]-N-ethyl-piperazine-1-sulfonamide. 1 ¹H-NMR [ppm] in CDCl₃: 1.21 (t, 3H), 3.14 (quintet, 2H), 3.11–3.22 (m, 2H), 3.25–3.43 (m, 4H), 3.65–4.10 (m, 2H), 4.19 (t, 1H), 5.54 (s, 2H), 6.71 (t, 1H), 7.08 (d, 1H), 7.23–7.28 (m, 2H), 7.89 (s, 1H). LC-MS (Method 1): RT = 1.06 min; [M+H] + = 560.

[0344] Example P4: 4-[6-[(4-bromophenyl)methoxy]-5-cyano-2-(difluoromethyl)pyridine-3-carbonyl]-N-ethyl 1-Piperazine-1-sulfonamide (compound P1.7):

[0345]

[0346] Step 1: 5-Cyano-2-(difluoromethyl)-6-hydroxypyridine-3-carboxylic acid

[0347]

[0348] Ethyl 5-cyano-2-(difluoromethyl)-6-hydroxy-pyridine-3-carboxylic acid (4.0 g, 17 mmol) synthesized as described in patent application WO 2017195703 of Soda Corporation was dissolved in ethanol (130 mL) and potassium hydroxide (3.3 g, 50 mmol, 2.9 equivalents) dissolved in ethanol (33 mL) was added. The reaction mixture was stirred under reflux for 20 hours. The reaction mixture was then diluted with ethyl acetate and 2 N hydrochloric acid. The mixture was extracted three times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over sodium sulfate, and the solvent was removed. 3.5 g of 5-cyano-2-(difluoromethyl)-6-hydroxy-pyridine-3-carboxylic acid as a white solid was obtained. 1 ¹H-NMR [ppm]: 7.59 (t, 1H), 8.58 (s, 1H), 13.75 (wide s, 2H). LC-MS (Method 2): RT = 0.23 min; [M+H] + = 215.

[0349] Step 2: 4-[5-cyano-2-(difluoromethyl)-6-hydroxy-pyridine-3-carbonyl]-N-ethyl-piperazine-1-sulfonamide

[0350]

[0351] To a solution of 5-cyano-2-(difluoromethyl)-6-hydroxypyridine-3-carboxylic acid (2.00 g, 9.34 mmol) in ethyl acetate (140 mL), N-ethylpiperazine-1-sulfonamide (2.71 g, 14 mmol, 1.5 equivalents), N,N-diisopropylethylamine (8.13 mL, 46.7 mmol, 5.0 equivalents), and propanephosphonic anhydride (T3P, 10.7 g, 10.0 mL, 16.8 mmol, 1.8 equivalents; 50% solution in ethyl acetate) were added. The reaction mixture was stirred at room temperature for 18 hours and then quenched with 2 NHCl. The mixture was diluted with water and extracted three times with 2-methyl-THF. The combined organic layers were dried over Na₂SO₄, filtered, and concentrated under reduced pressure. The residue was suspended in methanol and filtered to give 2.00 g of 4-[5-cyano-2-(difluoromethyl)-6-hydroxy-pyridine-3-carbonyl]-N-ethyl-piperazine-1-sulfonamide as a white solid. 1 ¹H-NMR [ppm] in DMSO-d6: 1.03 (t, 3H), 2.96 (quintet, 2H), 2.95–3.18 (m, 4H), 3.23–3.45 (m, 2H), 3.58–3.75 (m, 2H), 6.91 (t, 1H), 7.34 (t, 1H), 8.38 (s, 1H), 13.62 (broad s, 1H). LC-MS (Method 1): RT = 0.55 min; [M+H] + = 390.

[0352] Step 3: 4-[6-[(4-bromophenyl)methoxy]-5-cyano-2-(difluoromethyl)pyridine-3-carbonyl]-N-ethyl-piperazine-1-sulfonamide (compound P1.7)

[0353]

[0354] Potassium carbonate (272 mg, 1.93 mmol, 3.0 equivalents) and sodium iodide (20 mg, 0.128 mmol, 0.2 equivalents) were added to a solution of 4-[5-cyano-2-(difluoromethyl)-6-hydroxy-pyridine-3-carbonyl]-N-ethyl-piperazine-1-sulfonamide (250 mg, 0.642 mmol) in acetone (3.2 mL), followed by the addition of 1-bromo-4-(bromomethyl)benzene (180 mg, 0.706 mmol, 1.1 equivalents). The reaction mixture was stirred at 70°C for 4 hours. The suspension was then filtered. The residue was washed with acetone, dried under vacuum, suspended in methanol, filtered, and dried to give 240 mg of 4-[6-[(4-bromophenyl)methoxy]-5-cyano-2-(difluoromethyl)pyridine-3-carbonyl]-N-ethyl-piperazine-1-sulfonamide (compound P1.7). 1 ¹H-NMR [ppm] in CDCl₃: 1.22 (t, 3H), 3.12 (quintet, 2H), 3.10–3.44 (m, 6H), 3.72–4.08 (m, 2H), 4.28 (t, 1H), 5.04 (s, 2H), 6.71 (t, 1H), 7.39 (d, 2H), 7.55 (d, 2H), 7.90 (s, 1H). LC-MS (Method 1): RT = 1.04 min; [M+H] + = 558 / 560.

[0355] The compounds in Tables P1 and P2 are prepared by methods described in the examples above or similar methods.

[0356] Table P1: Compounds with formula (Ia)

[0357] (Ia)

[0358] The compounds in Table P1 can be prepared by methods described in the examples above or similar. The following abbreviations are used in the tables below: RT = retention time, min = minutes.

[0359] Table P1:

[0360]

[0361] Table P2: Compounds with formula (Ib)

[0362] (Ib)

[0363] The compounds in Table P2 can be prepared by methods described in the examples above or similar. The following abbreviations are used in the tables below: RT = retention time, min = minutes.

[0364] Table P2:

[0365]

[0366] The intermediates in Table U1 are novel and can be used in the synthesis of some compounds with general structure I. They can be prepared by methods described in the examples above or similar methods. The following abbreviations are used in the tables below: RT = retention time, min = minutes.

[0367] Table U1:

[0368]

[0369] Table C: Comparative Compounds

[0370]

[0371] The activity of the compositions according to the invention can be significantly broadened and adapted to general conditions by adding other insecticidal, acaricidal, and / or fungicidal activities. Mixtures of compounds having formula (I) with other insecticidal, acaricidal, and / or fungicidal activities can also have additional unexpected advantages, which can be described more broadly as synergistic activity. For example, better plant tolerance, reduced phytotoxicity, control of insects at different developmental stages, or better behavior during their production (e.g., during grinding or mixing, during storage, or during use).

[0372] Suitable active ingredients to be added here are, for example, representatives of the following categories of active ingredients: organophosphorus compounds, nitrophenol derivatives, thiourea, juvenile hormones, formamidin, benzophenone derivatives, urea, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylurea, pyridylmethylene amino derivatives, macrolides, neonicotinoids, and Bacillus thuringiensis preparations.

[0373] The following combinations (or mixtures) of compounds having formula (I) and another active substance in a 1:1 weight ratio are preferred (the abbreviation "TX" means "a compound selected from the compounds defined in Tables 1 to 4 and Tables P1 to P2"):

[0374] (7E,9Z)-Dodec-7,9-dien-1-yl acetate + TX, (9Z,11E)-Tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-Tetradec-9,12-dien-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-Tedec-4-en-1-yl acetate + TX, (E,Z)-Tetradec-4,10-dien-1-yl acetate + TX, (Z)-Dodec-7-en-1-yl acetate + TX, (Z)-Hexadec-11-en-1-yl acetate + TX, (Z)-Hexadec-11-enal + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-eicos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, 1,2-dibromo-3-chloropropane + TX, 1,2-dichloropropane + TX, 1,2-dichloropropane and 1,3-dichloropropene + TX, 1,3-dichloropropene + TX, 14-methyloctadec-1-ene + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 2-(octylthio)ethanol + TX, 2-[5-(2-chloro-3,3,3-trifluoro-prop-1-enyl)-1-methyl-imidazol-2-yl]-5-cyclopropyl-3-ethylsulfonyl-pyridine + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 4-(quinoxalo-2-ylamino)benzenesulfonamide + TX, 4-methylnon-5-ol and 4-methylnon-5-one + TX, 5-methyl-6-thio-1,3,5-thiadiazin-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 8-hydroxyquinoline sulfate + TX, avermectin + TX, miticide + TX, acetamiprid + TX, acetamiprid + TX, flufenoxuron + TX, acynonapyr + TX, Cotton brown belt moth GV + TX, difenoconazole + TX, afolanar + TX, *Agrobacterium radioduran* + TX, AKD-3088 + TX, cotton bollworm + TX, aldicarb + TX, aldicarb + TX, propyrene + TX, cis-cypermethrin + TX, lambda-cyhalothrin + TX, alpha-multistriatin + TX, *Amblyseius* species +TX, Sulfamethoxam + TX, Amino Acids + TX, Cypermethrin + TX, Celery Earworm NPV + TX, *Protoceratops chinensis* + TX, *Aphidius septemlobus* + TX, Cotton Aphid Parasitic Wasp + TX, Aphid Gall midge + TX, Azoxystrobin + TX, Alfalfa Silver-striped Earworm NPV + TX, AZ 60541 + TX, Azadirachtin + TX, Triazole Tin + TX, Bacillus spp. *Aphidius* + TX, *Bacillus chitinosporus* AQ746 (NRRL Registry No. B-21 618) + TX, *Bacillus stolonifer* + TX, *Bacillus kurstak* + TX, *Bacillus mycosisrin* AQ726 (NRRL Registry No. B-21664) + TX, *Bacillus pumilus* (NRRL Registry No. B-30087) + TX, Bacillus pumilus AQ717 (NRRL accession number B-21662) + TX, Bacillus species AQ175 (ATCC accession number 55608) + TX, Bacillus species AQ177 (ATCC accession number 55609) + TX, Bacillus species AQ178 (ATCC accession number 53522) + TX, Bacillus spheroidae + 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 registry number B-21665) + TX, Bacillus subtilis not specified + TX, Bacillus thuringiensis AQ52 (NRRL registry number B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL registry number B-21530) + TX, Bacillus thuringiensis + TX, Bacillus thuringiensis subsp. Ayuzawa + TX, Bacillus thuringiensis subsp. Israel + TX, Bacillus thuringiensis subsp. Japan + TX, Bacillus thuringiensis subsp. Kurstak + TX, Bacillus thuringiensis subsp. Tenebrionis + TX, Bacillus thuringiensis subsp. Kurstak BMP 123 + TX, Beauveria bassiana + TX, Beauveria bassiana + TX, Benzyl + TX, Benomyl + TX, chlorpyrifos + TX, benzimidone (CAS No.: 2566451-67-8) + TX, benzimidone + TX, pyrimethanil + TX, β-cyhalothrin + TX, β-cypermethrin + TX, cypermethrin + TX, bifenazate + TX, bifenthrin + TX, chlorfenapyr + TX, bio-allethrin + TX, bio-benzylfuran +TX, bis(tributyltin) oxide + TX, bis(aziridine)methylaminophosphine sulfide + TX, bis(triflufenoxuron) + TX, flufenoxuron + TX, brevicomin + TX, broflanilide + TX, deltamethrin + TX, bromoacetamide + TX, thiophanate-ethyl + TX, bromonitol + TX, busulfan + TX, methyl ethyl ketone + TX, butopyronoxyl + TX, butoxy(polypropylene glycol) + TX, butylpyridaben + TX, thion + TX, calcium arsenate + TX, carbofuran + TX, carbon disulfide + TX, thiophanate-methyl + TX, batatan + TX, CAS No.: 1594624-87-9 +TX, CAS No.: 1922957-47-8 + TX, CAS No.: 1255091-74-7 + TX, CAS No.: 1365070-72-9 + TX, CAS No.: 158062-71-6 + TX, CAS No.: 1594626-19-3 + TX, CAS No.: 1594637-65-6 + TX, CAS No.: 1632218-00-8 + TX, CAS No.: 1808115-49-2 + TX, CAS No.: 1922957-46-7 + TX, CAS No.: 1922957-48-9 + TX, CAS No.: 1956329-03-5 + TX, CAS No.: 1990457-52-7 + TX, CAS No.: 1990457-55-0 + TX, CAS No.: 1990457-57-2 + TX, CAS No.: 1990457-66-3 + TX, CAS No.: 1990457-77-6 + TX, CAS No.: 1990457-85-6 + TX, CAS No.: 2032403-97-5 + TX, CAS No.: 2044701-44-0 + TX, CAS No.: 2095470-94-1 + TX, CAS No.: 2128706-05-6 + TX, CAS No.: 2133042-31-4 + TX, CAS No.: 2133042-44-9 + TX, CAS No.: 2171099-09-3 + TX, CAS No.: 2220132-55-6 + TX, CAS No.: 2396747-83-2 + TX, CAS No.: 2408220-91-5 + TX, CAS No.: 2408220-94-8 + TX, CAS No.: 2415706-16-8 + TX, CAS No.: 2583740-14-9 +TX, CAS No.: 2583751-98-6 + TX, CAS No.: 2719848-60-7 + TX, CAS No.: 2898489-71-7 + TX, CAS No.: 34763-86-5 + TX, CAS No.: RNA (Potato Beetle-Specific Recombinant Double-Strand Interference GS2) + TX, Chlorantraniliprole + TX, Chlordane + TX, Bromnifloxacin + TX, Chlorothalonil + TX, D-trans-Cypermethrin + TX, Chlorpyrifos + TX, Cyclofenac + TX, Chrysoperla carnea + TX, Clenbuterol + TX, Naproxetine + TX, Thiamethoxam + TX, Codlelure + TX, Codlemone + TX, Copper Acetate + TX, Copper Dioctanoate + TX TX, copper hydroxide + TX, copper sulfate + TX, cresol + TX, phosmet + TX, Cryptolaemus montrouzieri + TX, melon fly pheromone + TX, benzoylphosphonate + TX, bromocyanamide + TX, oxazolidinone (CAS No.: 2128706-04-5) + TX, cyclopyridoxine + TX, cyclobromin + TX, trifluralin + TX, cypermethrin + TX, epoxim + TX, codling moth GV + TX, cypermethrin + TX, etoxazole + TX, diflubenzuron + TX, lambda-cyhalothrin + TX, cyhalothrin + TX, deltamethrin + TX, cyprodinil + TX, cyprodinil + TX, cyprodinil + TX, cyprodinil + TX, cyprodinil + TX, cyprodinil + TX, cyromazine + TX, cyromazine + TX, cytokinin + TX, Siberian Dacnusa sibirica + TX, Dazomet + TX, DBCP + TX, DCIP + TX, deltamethrin + TX, diethyl ether + TX, chlorpyrifos + TX, fenpropathrin + TX, dibromophos + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, dichloronaphthoquinone + TX, dichlorophenol + TX, dicliphos + TX, dichlorothiamethoxam + TX, DEET + TX, diflubenzuron + TX, Diglyphus isaea + TX, sterile amine + TX, dimethoate + TX, mosquito repellent + TX, dimethyl phthalate + TX, chlorfenapyr + TX, dinactin + TX, abamectin + TX TX, fipronil + TX, phosmet + TX, pyraclostrobin + TX, nonadecanedane+ TX, D-limonene + TX, dodecano-8-en-1-yl acetate + TX, dodecano-9-en-1-yl acetate + TX, dodecano-8,10-dien-1-yl acetate + TX, multi-emodin + TX, domi attractant + TX, doramectin + TX, emamectin + TX, emamectin benzoate + TX, dextromethorphan + TX, Encarsia formosa + TX, cypermethrin + TX, isodrin + TX, epoxim + TX, ε-methoxyflufenoxuron + TX, ε-methoxybenzylflufenoxuron + TX, Eretmocerus eremicus + TX, cypermethrin + TX, ethion + TX, acetamiprid + TX, ethoprofen + TX, ethyl 4-methyloctanoate + TX, ethylhexanediol + TX, Dibromoethane + TX, Ethylhexyl + TX, Etoxazole + TX, Etoxazole + TX, Eugenol + TX, Seaweed Extract and Molasses-Derived Fermentation Products + TX, Seaweed Extract and Molasses-Derived Fermentation Products Containing Urea + TX, Seaweed Extract and Fermented Plant Products + TX, Seaweed Extract and Fermentation Products Containing Plant Hormones, Vitamins, EDTA-chelated Copper, Zinc and Iron + TX, Valproate + TX, Sodium Dimethoate + TX, Benzophos + TX, Quinoxyfen + TX, Penflubenzuron + TX, Fenitrothion + TX, Dimethoate + TX, Butyricin + TX, Benthiocarb + TX, Fenoxycarb + TX, Cypermethrin + Tx, Fenpyrad + TX, Azoxystrobin + TX, Fentoxazone + TX, Fenthion + TX, Triphenyltin + TX, Triphenyltin Acetate + TX, Cypermethrin + TX, Ferric Phosphate + TX, Fipronil + TX, Flufenoxuron + TX, Flupyridine + TX, Pyrimethanil + TX, Trifluralin + TX, Acetobacter + TX, Flubendiamide + TX, Flufenoxuron + TX, Fluchlorfenapyr + TX, Flucitrinate + TX, Flucyclovir + TX, Cypermethrin + TX, Flufenoxuron + TX, Flufenoxuron [318290-98-1] + TX, Flufenoxuron + TX, Pyrimethanil + TX, Trifluralin + TX, Difenoconazole + TX, Flupyrazole + TX, Flupyridine + TX, Flurranazine + TX, Flufenoxuron + TX, Flufenoxuron + TX, Flufenoxuron + TX, Flufenoxuron + TX, Flufenoxuron + TX, Flufenoxuron + TX, Flufenoxuron + TX, Flufenoxuron + TX, Flufenoxuron + TX TX, fluoxazolamide + TX, formaldehyde + TX, thiazophosphine +TX, thionyl phosphate + TX, Southern pine bark beetle pheromone + TX, furfural + TX, graphite methyl methacrylate (CAS No.: 2644770-30-7) + TX, high-efficiency cyhalothrin + TX, Gossyplure® (a 1:1 mixture of (Z,E) and (Z,Z) isomers of hexadecano-7,11-dien-1-yl-acetate) + TX, cotton weevil pheromone + TX, cotton weevil pheromone I + TX, cotton weevil pheromone II + TX, cotton weevil pheromone III + TX, cotton weevil pheromone IV + TX, granulovirus + TX, pendimethalin + TX, GY-81 + TX, benzyl ether + TX, chlorfenapyr + TX, hypersensitive protein + TX, cotton bollworm nucleopolyhedrovirus + TX, corn armyworm NPV + TX, corn armyworm nucleopolyhedrovirus + TX, Cotton bollworm nucleopolyhedrovirus + TX, Tobacco bud moth nucleopolyhedrovirus + TX, Hexamethyl melamine + TX, Hexamethyl phosphonate + TX, Heptamethrin + TX, Phosphate + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hexobarbital + TX, Thiamethoxam + TX, Spotted ladybug + TX, Fluroxypyr + TX, Mercaptan + TX, Quicklime + TX, Imidacloprid + TX, Imidacloprid + TX, Propyrethroid + TX, Indoxam + TX, Indoxacarb + TX, Ioprofen + TX, Tebufenozide + TX, Tebufenozide + TX, Isoprofenozide + TX, Chlorpyrifos + TX, isoxaflutole + TX, oxadiazon (CAS No.: 2892524-05-7) + TX, isopyram + TX, ivermectin + TX, scarab beetle pheromone + TX, κ-bifenthrin + TX, κ-heptafluthrin + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, kinetin + TX, lambda-cyhalothrin + TX, ledprona + TX, resveratrol + TX, citrus scale insect parasitic wasp + TX, trimethyldioxane + TX, litlure + TX, white armyworm pheromone + TX, lotelanar + TX, lufenuron + TX, mirid bug + TX, cabbage looper NPV + TX, methyl phosmet + TX, attractant + TX, megatomoicacid + TX, cyfluthrin + TX, metaldehyde + TX, β-Beta + TX, β-Beta potassium salt + TX, β-Beta sodium salt + TX, *Metarhizium anisopliae* + TX, *Metarhizium anisopliae* + TX, *Metarhizium anisopliae* microsporum variant +TX, *Metarhizium anisopliae* species + TX, methyl thiophanate + TX, cypermethrin + TX, thiophanate-methyl + TX, methomyl + TX, methylquinalkonium chloride + TX, methoxyfenozide + TX, methylphosphonazine + TX, methyl bromide + TX, chlorfenapyr + TX, methyl isothiocyanate + TX, methyl neodecanoate + TX, methoxyfenozide + TX, cypermethrin + TX, chlorfenapyr + TX, milbemime + TX, methoxyfenozide + TX, doxycycline + TX, pyridaben + TX, malathion + TX, moxifloxacin + TX, pyridaben + TX, putrefactive white fungus 620 (NRRL Registry No. 30547) + TX, *Muscodor roseus* A3-5 (NRRL Registry No. 30548) + TX, *Lysimachia verrucae* composition + TX, sodium mancozeb + TX, NC-184 + TX, Neem-based products + TX, Neodiprionsertifer NPV and N. lecontei NPV + TX, bis(dimethyldithiocarbamate) nickel + TX, niclosamide + TX, niclosamide-ethanolamine + TX, acetamiprid + TX, nitenpyram + TX, trichloromethylpyridine + TX, octadecanoic acid-2,13-dien-1-yl acetate + TX, octadecanoic acid-3,13-dien-1-yl acetate + TX, octathiazone + TX, omethoate + TX, hymexazol + TX, small flower bug species + TX, coconut beetle aggregation pheromone + TX, fenvalerate + TX, oxaloacetate + TX, oxazolidin + TX, oxazolidin + TX, oxadiazine + TX, oxadiazine + TX, oxadiazine + TX, oxytetracycline + TX TX, *Paecilomyces rosenbergii* + TX, *Paecilomyces lilacinus* + TX, parathion-ethyl + TX, *Paecilomyces szawa* + TX, *Paecilomyces punctata* + TX, *Paecilomyces cladosporioides* + TX, *Paecilomyces cerevisiae* + TX, *Paecilomyces cerevisiae* + TX, p-cypermethrin + TX, flufenoxuron + TX, pentachlorophenol + TX, permethrin + TX, phenoxybenzyl + TX, phorate + TX, phosphamidon + TX, phosphamidon + TX, phosmet + TX, phosmet + TX, phytosylcarbide + TX, picaridin + TX, thiophanate-methyl + TX, piperazine + TX, flufenoxuron (CAS No.: 2615135-05-0) + TX, piperonyl butyl ether + TX, pirimicarb + TX, pyrimidinium-ethyl + TX, pyrimidinium-methyl + TX, diamondback moth granulovirus + TX, diamondback moth nucleopolyhedrovirus + TX, polyhedrosis virus + TX, potassium and molybdenum and EDTA chelated manganese + TX, potassium ethyl xanthate + TX, potassium hydroxyquinoline sulfate +TX, propargite + TX, thiabendazole + TX, profenofos + TX, propofol + TX, chlorfenapyr + TX, acetamiprid + TX, propoxur + TX, propoxur + TX, propoxur + TX, propoxur + TX, propoxur + TX, pyrimethanil + TX, pymetrozine + TX, pyrazophos + TX, pyrethrum + TX, pyridaben + TX, pyridaben + TX, pyridaben + TX, pyridaben + TX, pyridaben + TX, flufenoxuron + TX, pyrimethanil + TX, pyrimethanil + TX, pyrazophos + TX, pyrazophos + TX, pyrazophos + TX, pyrazophos + TX, pyrazophos + TX, pyrazophos + TX, pyrazophos + TX, pyrazophos + TX, QRD 420 (terpene blend) + TX, QRD 452 (terpene blend) + TX, QRD460 (terpene blend) + TX, soapberry + TX, Alginate + TX, Quinoline + TX, Benzylfuran + TX, Rhodococcus aureus AQ719 (NRRL Registry No. B-21663) + TX, Sarolaner + TX, S-Bio-Allethrin + TX, Ketoconazole + TX, Silaketin + TX, Insect-attracting Ring + TX, Flumethrin + TX, Simazine + TX, Sodium Pentachlorophenoxide + TX, Banana Bulb Weevil Attractant (sordidin) + TX, Spidoxacarb + TX, Ethyl Spinosad + TX, Spinosad + TX, Spirodiclofen + TX, Spirodiclofen + TX, Spirodiclofen + TX, Ethyl Methoxyfen + TX, Spirodiclofen + TX, Beet Armyworm Nucleopolyhedrovirus + TX, Fall Armyworm Nucleopolyhedrovirus + TX, hairy nematode + TX, small leafroller nematode + TX, noctuid moth nematode + TX, Grignard nematode + TX, Rhabditis nematode + TX, Steinernema riobravis + TX, mole cricket nematode + TX, nematode species + TX, Streptomyces flavus (NRRL registry number 30232) + TX, Streptomyces species (NRRL registry number B-30145) + TX, streptomycin + TX, streptomycin sesquisulfate + TX, strychnine + TX, tebufenozide + TX, thiophanate-methyl (CAS number: 2377084-09-6) + TX, sulfadiazine + TX, thiamethoxam + TX, tebufenozide + TX, pyridaben + TX, butylpyrimidine + TX, chlorothalonil + TX, pyridaben ... TX, tert-butylcarbate + TX, tert-butylphosphide + TX, terpene blend + TX, tetrachlorantraniliprole + TX, tetrachlorothiophene + TX, tetradec-11-en-1-ylacetate+TX, Tetrachlorfenapyr + TX, Acephate + TX, Tetrafluthrin + TX, Acaricide + TX, Flufenoxuron + TX, θ-Cypermethrin + TX, Thiafenox + TX, Thiamethoxam + TX, Cypermethrin + TX, Thiamethoxam + TX, Thiamethoxam + TX, Thiamethoxam + TX, Thiammonium thiophanate + TX, Thiamethoxam + TX, Thiamethoxam + TX, Thiamethoxam + TX, Thiamethoxam + TX, Thiamethoxam + TX, Thiamethoxam (CAS No.: 1255091-74-7) + TX, Tigorana + TX, Thiamethoxam + TX, Tioxazafen + TX, Azoxystrobin + TX, Toxaphene + TX, Tetrabromopyrethrin + TX, Tetrafluthrin + TX, Tratamide + TX, Azoxystrobin + TX, Triazophos + TX, Azoxystrobin + TX, Tributyltin Oxide + TX, Trichlorfon + TX, Toxamethonium + TX, Trichlorfon + TX, Trichogrammae + TX, Snail Killer + TX, Trifluralin + TX, Trifluralin + TX, Mediterranean Fruit Fly Attractant + TX, Mediterranean Fruit Fly Attractant A + TX, Mediterranean Fruit Fly Attractant B1 + TX, Mediterranean Fruit Fly Attractant B2 + TX, Mediterranean Fruit Fly Attractant C + TX, Mixed Carbendazim + TX, Triphenyltin Acetate + TX, Triphenyltin Hydroxide + TX, Trunc-Call + TX, Tyclopyrazoflor + TX, Western Blind Mite + TX, Urethroid + TX, Verticillium + TX, Verticillium Species + TX, Xylenol + TX, YI-5302 + TX, Zeatin + TX, ζ-Cypermethrin + TX;

[0375] 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-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methylformamidinium (these compounds can be prepared by the method described in WO2019 / 110427) + TX, (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl ketone (these compounds can be prepared by ... (Prepared by the method described in WO 2017 / 220485) + TX, methyl 2-amino-6-methyl-pyridin-3-carboxylic acid (4-phenoxyphenyl) (this compound can be prepared by the method described in WO 2014 / 006945) + TX, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] ketone + TX, (7E,9Z)-dodec-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-tetadecedec-4-en-1-yl acetate + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazol-4-carboxamide + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-eicosode-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, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine (this compound can be prepared by the method described in WO 2018 / 153707) +TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]thiazolyl-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate + TX, 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, 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, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds can be prepared by the method described in WO 2017 / 025510) + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dibromo-3-chloropropane + TX, 1,2-dichloropropane and 1,3-dichloropropene + TX, 1,3-dichloropropene + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazole-5-one + TX, 10-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX, 1-bromo-2-chloroethane + TX, 1-dichloro-1-nitrobenzene + TX, 1-hydroxy-1H-pyridin-2-thione + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazole-5-one + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(1,3-dithiopentane-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl piperate +TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolane-2-yl)phenylmethylcarbamate + TX, 2-(4-chloro-3,5-dimethylmethyloxy)ethanol + TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indane-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indane-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indane-4-yl]pyridine-3-carboxamide + TX (This compound can be prepared by the method described in WO 2014 / 095675) + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(octylthio)ethanol + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl-2-ethylsulfinyl ethylmethyl phosphate + TX, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2,6-dimethyl-1H,5H-[1,4]dithia[2,3-c:5,6-c']bipyrrole-1,3,5,7(2H,6H)-tetraone (this compound can be derived from WO Prepared by the method described in WO 2011 / 138281) + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolinyl)oxy]phenyl]prop-2-ol + TX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (this compound can be prepared by the method described in WO 2017 / 029179) + TX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (this compound can be prepared by the method described in WO 2017 / 029179) + TX, 2-chlorovinyl diethyl phosphate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 2-imidazolinone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methyl carbamate + TX, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared by the method described in WO 2018 / 065414) + TX, 2-cyanothioethyl laurate +TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolinyl)-7,8-dihydro-6H-cyclopentadien[e]benzimidazole (these compounds can be prepared by the method described in WO 2016 / 156085) + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazol-4-carboxamide + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxynitrile (this compound can be prepared by WO 2016 / 156085) + TX, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxynitrile (these compounds can be prepared by the method described in WO 2016 / 156085) + TX, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxynitrile (these compounds can be prepared by ... (Prepared by the method described in WO 2016 / 156290) + TX, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazolium-4-carboxynitrile (this compound can be prepared by the method described in WO 2016 / 156290) + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid + TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-methyl-1-phenylpyrazole-5-yl dimethylcarbamate + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazin-3-carboxynitrile + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethyl-pyrazole-3-amine + TX, 4-(quinoxaloline-2-ylamino)benzenesulfonamide + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-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, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isooxazolin-3-one + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile +TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioalkyl-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-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazine-3-one + TX, 4-chlorophenylphenyl sulfone + TX, 4-methyl(prop-2-ynyl)amino-3,5-dimethylmethylcarbamate + TX, 4-methylnon-5-ol and 4-methylnon-5-one + TX, 5-(1,3-benzodioxane-5-yl)-3-hexylcyclohex-2-enone + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-3-one + TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate + TX, 5-amino-1,3,4-thiadiazol-2-thiol zinc salt (2:1) + TX, 5-methyl-6-thio-1,3,5-thiadiazine-3-ylacetic acid + TX, 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (which can be prepared by the method described in WO 2020 / 109391) + TX, 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (which can be prepared by the method described in WO 2020 / 109391) + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (which can be prepared by the method described in WO 2020 / 109391) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithia[1,2-c]isothiazolyl-3-carboxynitrile + TX, 6-isopentenylaminopurine + 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, 8-hydroxyquinoline sulfate + TX, Aspergillus+TX, Acetaminophen + TX, Aramacin + TX, Aramacin-S-methyl + TX, Acrylonitrile + TX, Cotton Brown Leaf Roller GV + TX, Agrobacterium radiata + TX, Aldicarb + TX, Aldrin + TX, Alpromethazine + TX, Dimethomorph + TX, α-Chlorohydrin + TX, α-Decidin + TX, α-Polycarb + TX, Aluminum Phosphide + TX, Amphetus species + TX, Amectotractin + TX, Azoxystrobin + TX, Cypermethrin + TX, Phosphamidon + Tx, Dimethomorph + TX, Ampicillin + TX, Indoxamyl + TX, Ammonium oxadixyl + TX, Amitraz + TX, Neonicotinic acid + TX, Celery Earworm NPV + TX, Pyrimidinol + TX, Dimethomorph + TX, Fluorophenyladenine + TX, Anthraquinone + TX, Antoxin + TX, Short-spur Aphid Parasite + TX, Cotton Aphid Parasite + TX, Aphid Gall Moth + TX, Azoxystrobin + TX, Acaricide + TX, Arsenic Trioxide + TX, Ethyl Chlorpyrifos + TX, Alfalfa Silver-striped Armyworm NPV + TX, Azaconazole + TX, Methylpyridinium + TX, Azobenzene + TX, Azophos + TX, Azoxystrobin + TX, Bacillus spheroides + TX, Bacillus thuringiensis δ-endotoxin + TX, Barium Carbonate + TX, Barium Hexafluorosilicate + TX, Barium Polysulfide + TX, Fumethrin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, Beauveria bassiana + TX, Benzophenone + TX, Benzyl + TX, Benzothiamethoxam + TX, Benzothiamethoxam + TX, Benzothiamethoxam + TX TX, bensulfuron-methyl + TX, bensulfuron-methyl + TX, benzoyl benzoate + TX, β-cyhalothrin + TX, β-cypermethrin + TX, cypermethrin + TX, pendimethalin + TX, bio-cypermethrin + TX, bis(2-chloroethyl) ether + TX, bis(tributyltin) oxide + TX, bis(aziridine)methylaminophosphine sulfide + TX, bismuth subtilis + TX, bifenthrin + TX, bifenthrin + TX, blasticidin-S + TX, borax + TX, Bordeaux mixture + TX, boscalid + TX, western pine bark beetle pheromone + TX, bromadiolone + TX, bromadiolone + TX, bromadiolone + TX, bromophenylenephos + TX, bromoacetamide + TX, bromophenylenephos + TX TX, Bromo-DDT + TX, Bromothion + TX, Bromodimethalin + TX, Fenoxacillin + TX, Bronitrothion + TX, Dimethoate +TX, Ethylpyrimethanil Sulfate + TX, Thiazide + TX, Busulfan + TX, N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate butyl-3-yne ester + TX, Butylcarbamate + TX, Terfenoxam + TX, Butylcarbamate + TX, Dimethoate + TX, Butoxyl (polypropylene glycol) + TX, Butylcarbamate sulfonate + TX, Butylpyridinium + TX, Calcium Arsenate + TX, Calcium Cyanide + TX, Calcium Polysulfide + TX, Camphene Octadec + TX, Captan + TX, Captan + TX, Chlorpyrifos + TX, Carbendazim + TX, Carbon Disulfide + TX, Carbon Tetrachloride + TX, Trithion + TX, Carbendazim + TX, Bataan Hydrochloride + TX, CAS No.: 2454319-63-0 + TX, CAS No.: 83-46-5 + TX, Servadine + TX, Acaricide + TX, Chlorpyrifos + TX, Acaricide + TX, Borneol + TX, Chlordane + TX, Decachlor + TX, Amitraz + TX, Amitraz Hydrochloride + TX, Dichlorvos + TX, Dichlorvos + TX, Dichlorvos + TX, Dichlorvos + TX, Dichlorvos + TX, Dichlorvos + TX, Dichlorvos + TX, Chlorpyrifos + TX, Chlorothalonil + TX, Chlorothalonil + TX, Chlorothalonil + TX, Propyl chlorpyrifos + TX, Chlorothalonil + TX, Chlorothalonil + TX, Chlorpyrifos + TX, Chlorpyrifos + TX, Ethylmethrin + TX, Cholecalciferol + TX, common lacewing + TX, ciprofloxacin I + TX, ciprofloxacin II + TX, ciprofloxacin + TX, cis-resmethrin + TX, cypermethrin + TX, clotrimazole + TX, dodecadienol + TX, codlemone + TX, copper acetylacetonate + TX, copper arsenate + TX, copper dioctanoate + TX, copper hydroxide + TX, copper naphthenate + TX, copper oleate + TX, copper oxide + TX, copper oxychloride + TX, chlorpyrifos + TX, phosmet + TX, phosmet + TX, naphthalene + TX, jiaxiangjunzhi + TX, phosmet + TX, eugenol + TX, cresol + TX, pyrimidine + TX, clomiphene + TX, phosmet + TX, phosmet + TX, cryolite + TX, *Cryptospira moniliformis* + TX, CS 708 + TX, pyridaben + TX, thiamethoxam + TX, benzonitrile+ TX, pyrethroid + TX, phosmet + TX, cymoxanil + TX, cyclopropane + TX, pyrethrum + TX, trifluralin + TX, codling moth GV + TX, cycloflufenicol + TX, abamectin + TX, cymoxanil + TX, cyclohexane + TX, pyrimethanil + TX, phosmet + TX, cytokinin + TX, Siberian chamaejasper + TX, DAEP + TX, dazomet + TX, DCIP + TX, DCPM + TX, DDT + TX, imidacloprid + TX, demethylcarbofuran + TX, phosmet + TX, phosmet-O + TX, phosmet-S + TX, demeton-methyl + TX, demeton-O + TX, demeton-O-methyl + TX, demeton-S + TX, demeton-S-methyl + TX TX, demeton-S-methylsulfon + TX, chlorpyrifos + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, isochlorpyrifos + TX, dichlorvos + TX, chlorpyrifos + TX, bactericide + TX, dichloronaphthoquinone + TX, dichlorophenol + TX, dichlorvos + TX, sclerotinia + TX, dichlorvos + TX, cypermethrin + TX, pyridaben + TX, chlorfenapyr + TX, chlorfenapyr + TX, diethylcarbamide + TX, diethylpyrazol-3-yl phosphate + TX, DEET + TX, dimethomorph + TX, difenoconazole + TX, dimethomorph + TX, flufenoxam + TX TX, Pea Leafminer Wasp + TX, Bantam + TX, Dimethoate + TX, Tetrafluoromethrin + TX, Mefenoxam + TX, Dimethoate + TX, Mefenoxam + TX, Mefenoxam + TX, Dimethoate + TX, Dimethoate + TX, Mosquito Repellent + TX, Dimethyl Phthalate + TX, Methyl Tortillaria + TX, Difenoconazole + TX, Difenoconazole + TX, Difenoconazole-4 + TX, Difenoconazole-6 + TX, Difenoconazole + TX, Amyl nitrate + TX, Pronitrophenol + TX, Pennitrophenol + TX, Diphenoxylate + TX, Oxyl Nitrate + TX, Nitrobutyl Nitrate + TX, Benzyl + TX, Phosphate + TX, Dichlorvos + TX, Ratnitrile + TX TX, sulfadiazine + TX, thiamethoxam + TX, dipyridoxine + TX, nonadecanedane + TX, dithionine + TX, dithionine+ TX, Thiamethoxam + TX, DNOC + TX, Dodecano-8-en-1-ylacetate + TX, Dodecano-9-en-1-ylacetate + TX, Dodecano-8 + TX, Dodecylmorpholine + TX, Dodecyl + TX, Dodecyl + TX, Phenoxypropyne + TX, Domi attractant + TX, Dolactin + TX, DSP + TX, D-methoxyphenoxyacetate + TX, Ecstatone + TX, Kebenzan + TX, EI 1642 + TX, EMPC + TX, Encarsia formosa + TX, Indomethacin + TX, Indomethacin + TX, Enstroburin + TX, Enoxastrobin + TX, EPBP + TX, Flutriafol + TX, Irinoctin + TX, Aphidida albicans + TX, Calcium alcohol + TX, Etaphos + TX, thiamethoxam + TX, ethylcarbendazim + TX, ethoprofen + TX, phosmet + TX, 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylic acid ethyl ester (which can be prepared by the method described in WO 2020 / 056090) + TX, 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylic acid ethyl ester (which can be prepared by the method described in WO 2020 / 056090) + TX, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester + TX, 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester (this compound can be prepared by the method described in WO 2018 / 158365) + TX, 4-methyloctanoic acid ethyl ester + TX, formate + TX, ethylhexane glycol + TX, dibromoethane + TX, dichloroethane + TX, ethylene oxide + TX, tebuconazole + TX, ethirimol + TX, ethirimol + TX, eugenol + TX, EXD + TX, oxadiazon + TX, farnesol + TX, farnesol with nerolidol + TX, imidacloprid + TX, sodium dichloroisocyanurate + TX, tebuconazole + TX, chlorpyrifos + TX, fenbutatin + TX, phosmet + TX TX, Quinoline (CAS No.: 2132414-04-9) + TX, Ethylcarbendazim + TX, Mefenoxam + TX, Cyclomethrin + TX, Fenitrothion + TX, Difenoconazole (CAS No.: 2344721-61-3) + TX, Benthiocarb + TX, Oxypyrimethanil + TX, Isoprothiolane+ TX, Seed dressing + TX, Fenpicoxamid + TX, Cypermethrin + TX, Benzoyl + TX, Butyroxim + TX, Fenpyrad + TX, Amifloxacin + TX, Acaricide + TX, Acaricide + TX, Fenoxam + TX, Fenthion + TX, Ethyl Fenthion + TX, Triphenyltin + TX, Flunitrodiphenylamine + TX, Ferrous Sulfate + TX, Azoxystrobin + TX, Ferric Phosphate + TX, Fludioxonil + TX, Diflubenzuron + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX, Fluazinam + TX TX, fluopyram + TX, fluopyram + TX, fluopyram + TX, fluazinam + TX, fluazinam + TX, fluoxastrobin + TX, fluoxastrobin + TX, fluopyram + TX, fluopyram + TX, fluazinam + TX, fluazinam hydrochloride + TX, fluquinazole + TX, flusilazole + TX, sulfadiazine + TX, fluoxastrobin + TX, fluoxastrobin + TX, fenbendazole + TX, fluopyram + TX, FMC 1137 + TX, captan + TX, formaldehyde + TX, chlorpyrifos + TX, chlorpyrifos hydrochloride + TX, carbendazim + TX, aluminum tris(ethyl phosphonate) + TX, phosmet + TX, phosphamidon + TX, phosmet + TX, southern pine bark beetle pheromone + TX, malathion + TX, Furazolidone + TX, Furazolidone + TX, Furazolidone + TX, Pyrethrum + TX, Furfural + TX, γ-HCH + TX, Frucamide + TX, Acaricide Mixture + TX, Acaricide Mixture I + TX, Acaricide Mixture II + TX, Acaricide Mixture III + TX, Acaricide Mixture IV + TX, Biguanide Octyl Salt + TX, Biguanide Octyl Acetate + TX, Benzylfentanyl + TX, HCH + TX, Hexamethylmelamine + TX, Hexamethylphos + TX, HEOD + TX, Heptachlor + TX, Phosphate + TX, Heterochloride + TX, Heterochloride and Heterochloride Megidis + TX, Hexaconazole + TX, Cetylcyclopropane Carboxylate + TX, Hexaconazole + TX, Hexaconazole + TX, Hexaconazole + TX, HHDN + TX, Ladybug + TX, Mercurochrome + TX, Quicklime + TX, Hydrogen Cyanide + TX, Hymexazol + TX, Quinoline+ TX, Imanin + TX, Imazalil + TX, Imidazole + TX, Biguanidine Octylamine + TX, Fluinbam + TX, Succinazole + TX, Isothiazinon + TX, Isotriflufenazole + TX, Isoprothiolane + TX, Isoprothiolane + TX, Propineb + ​​TX, Toothril Dienol + TX, Small Enol + TX, IPSP + TX, Isamidophos + TX, Chlorpyrifos + TX, Carbochlor + TX, Methamidophos + TX, Isofenphos + TX, Isofenphos + TX, Isoprothiolane + TX, Isoprothiolane + TX, Isoprothiolane + TX, Isoprothiolane + TX, Transplanting Agent + TX, Isoprothiolane + TX, Pyraclostrobin + TX, Isoprothiolane + TX, Oxadiazon + TX, Scarab Beetle Sex Toxicant + TX, Jasminyl I + TX, Jasminyl II + TX, Iodine-thion + TX, Juvenile Hormone I + TX, Juvenile Hormone II + TX, Juvenile Hormone III + TX, Thiamethoxam + TX, Kasugamycin + TX, Kasugamycin Hydrochloride Hydrate + TX, Chloramphenicol + TX, Kinetin + TX, Acetylpyridinium + TX, Azoxystrobin + TX, Lead Arsenate + TX, Citrus Scale Parasitic Wasp + TX, Bromophos + TX, Lindane + TX, Trimethyldioxane-Nonane + TX, Acetaminophen + TX, Noctuid Moth Sex Pluton + TX, White-spotted Noctuid Moth Sex Pluton + TX, Ivbenmixianan + TX, Thiazolium + TX, Mirid Bug + TX, Magnesium Phosphate + TX, Profenofosine + TX, Cabbage Noctuid Moth NPV + TX, Mancozeb + TX, Mancozeb + TX, Mandespin + TX, Dimethomorph + TX, Mancozeb + TX, Azoxystrobin + TX, m-isopropylphenyl methyl carbamate + TX, Phoxim + TX, Methyl phosmet + TX, Acetate + TX, Chlorfluazuron + TX, Megatomoic acid + TX, Phoxim + TX, Azoxystrobin + TX, Cypermethrin + TX, Dithiamethoxam + TX, Methionine + TX, Mercuric oxide + TX, Mercurous chloride + TX, Methyl sulfoxide + TX, Methyl sulfoxide + TX, Metalaxyl + TX, Magnetitan + TX, Magnetitan potassium salt + TX, Magnetitan sodium salt + TX, Yellow-spotted flea + TX, Metarhizium anisopliae + TX, Metarhizium anisopliae Microsporum var. spp. + TX, Pyridaben + TX, Ethiophanate-methyl + TX, Methyl thiamethoxam + TX, Acaricide + TX, Methylsulfonyl fluoride + TX, Sulfocarb + TX, thiophanate-methyl + TX, methoxyprolin + TX, methylquinolone + TX, methoxydiphenyl ether + TX, methoxydiphenyltrichloroethane + TX, methoxydiphenyltrichloroethane (DDT)+ TX, (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester + TX, (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (these compounds can be prepared by the method described in WO 2020 / 193387) + TX, (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate (these compounds can be prepared by the method described in WO 2020 / 079111) + TX, (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate + TX, methylphosphonazine + TX, bromomethane + TX, insecticide + TX, methyl isothiocyanate + TX, N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (can be prepared by the method described in WO 2020 / 097012) + TX, N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (can be prepared by the method described in WO 2020 / 097012) + TX, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, methyl chloroform + TX, dichloromethane + TX, methyl neodecanoamide + TX, mancozeb + TX, methamidophos + TX, metomi-nostrobin + TX, oxadixyl + TX, benomyl + TX, tetrazolium + TX, MGK 264 + TX, milbemime + TX, propanil + TX, methamidophos + TX, phosmet + TX, phosmet + TX, methamidophos + TX, cypermethrin + TX, styramine + TX, moxifloxacin + TX, pyraclostrobin + TX, cyproconazole + TX, methamidophos + TX, *Variococcus verrucosum* composition + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared by the method described in WO 2017 / 153380) +TX, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared by the method described in WO 2017 / 153380) + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin + TX, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin + TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds can be prepared by the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO2017 / 118689) + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-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-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide + TX, 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, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidinium (this compound can be prepared by the method described in WO 2016 / 202742) +TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidin + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidin (these compounds can be prepared by the method described in WO 2015 / 155075) + TX, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin (this compound can be prepared by the method described in IPCOM000249876D) + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidin + TX, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidin + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin + TX, N-[N-methoxy-C-methyl-carboimino]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared by the method described in WO 2018 / 202428) + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidin (these compounds can be prepared by the method described in WO 2018 / 228896) + TX, sodium mancozeb + TX, naphthylphosphide + TX, dibromophos + TX, naphthalene + TX, NC-170 + TX, Neodiprionsertifer NPV and N. lecontei NPV + TX, nerolidol + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidin + TX, bis(dimethyldithiocarbamate)nickel + TX, nicotine-ethanolamine + TX, nicotine sulfate + TX, flufenoxuron + TX, nicotinic acid +TX, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidin + TX, nitrazepam + TX, trichloromethylpyridine + TX, pendicarb + TX, pendicarb 1:1 zinc chloride complex + TX, phthalimide + TX, N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide + TX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenylthioamide + TX, glutathione + TX, fluorophenylpyrimidin + TX, O,O,O',O'-Tetrapropyl dithiophosphate + TX, Octadec-2,13-dien-1-yl acetate + TX, Octadec-3,13-dien-1-yl acetate + TX, Octathiazoline + TX, Furazolidone + TX, Oleic acid + TX, Omethoate + TX, Heconazole + TX, Small-flowered bug species + TX, Coconut beetle aggregation pheromone + TX, Oximethiophanate-methyl + TX, Filacon + TX, Oxysulfanilamide + TX, Glufosinate + TX, Oxysulfanilamide ... TX, isoprothiolane + TX, tebuconazole + TX, pendimethalin + TX, fluopyram + TX, flufenoxuron + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, pyraclostrobin + TX, permethrin + TX, pH 60-38 + TX, cyazofamid + TX, fenthion + TX, phosphamidon + TX, fenpyroxen + TX, chlorpyrifos + TX, thiophanate-methyl + TX, glyphosate + TX, parachlorfon + TX, phosphamidon + TX, phosphine + TX, phosphorus + TX, methyl phoxim + TX, phthalide + TX, phytoseidocarb + TX, piperazine + TX, picaridin + TX, azoxystrobin + TX, rodenticide + TX, piperazine + TX, piperonyl butyl ether + TX, synergistic aldehyde + TX, methamidophos + TX, polychlorinated dicyclopentadiene isomer + TX, chlorinated turpentine oil + TX, acaricide + TX, polyoxin + TX, potassium arsenite + TX, potassium ethyl xanthate + TX, potassium hydroxyquinoline sulfate + TX, potassium thiocyanate + TX, pp'-DDT + TX, precocious puberty agent I +TX, Precozid II + TX, Precozid III + TX, Aminopyrim + TX, Thiamethoxam + TX, Prochloraz + TX, Prochloraz + TX, Iprodione + TX, Procymidone + TX, Iprodione + TX, Mancozeb + TX, Cymoxanil + TX, Propiconazole + TX, Zineb + ​​TX, Procymidone + TX, Propiconazole + TX, Prothioconazole + TX, Prothioconazole + TX, Frylopimerethroid + TX, Fluopyram + TX, Azoxystrobin + TX, Azoxystrobin + TX, Azoxystrobin + TX, Pyridaben + TX, Bifenazate + TX, Pyridaben + TX, Pyrethroid + TX, Pyrethroid I + TX, Pyrethroid II + TX, Pyrethroid + TX, Pyraclostrobin + TX, Fluopyram + TX, Pyridazine + TX, Pyridazine + TX, Pyridaben + TX, Pyridaben + TX, Pyridaben + TX, Pyrmethrin + TX, Rodenticide + TX, Pyridaben + TX, Pyridaben + TX, Pyridaben + TX, Pyridaben + TX, Pyridaben + TX, Magnolia extract + TX, Quinoline + TX, Quinoline-methyl + TX, Alginate + TX, Fluopyram + TX, Quinoline + TX, Phosphatidylcholine + TX, Phosphatidylcholine + TX, Quinoline + TX, Quinoline + TX, Quinoline + TX, Quinoline + TX, Quinoline + TX, Quinoline + TX, Pentachloronitrobenzene + TX, R-1492 + TX, Iodosylamine + TX, Cypermethrin + TX, Polygonum cuspidatum extract + TX, Ribavirin + TX, R-Methamphetamine + TX, Rotenone + TX, Ryanoidin + TX, Rianodin + TX, S421 + TX, Veratrum nigrum + TX, Magnaporphine + TX, Onion glycoside + TX, Cymoxanil + TX, Ketoconazole + TX, Fluoxetine + TX, Silachlor + TX, Synergistic Powder + TX, Sesamin + TX, SI-0009 + TX, Insect Attractant Ring + TX, Simazine + TX, Silozolone + TX, Sodium Arsenite + TX, Sodium Cyanide + TX, Sodium Fluoride + TX, Sodium Fluoroacetate + TX, Sodium Hexafluorosilicate + TX, Sodium Pentachlorophenolate + TX, Sodium Selenate + TX, Sodium Tetrathiocarbonate + TX, Sodium Thiocyanate + TX, Threthonium + TX, Banana Bulb Weevil Attractant (sordidin) + TX, Spirocyclophosphamide + TX, SSI-121 + TX, Hairy Moth Nematode + TX, Small Roller Nematode (Stokes' Nematode) + TX, Noctuid Moth Nematode + TX, *Nematodes gravidarum* + TX, *Nematodes rubescens* + TX, *Steinernema riobravis* + TX, *Nematodes riobravis* +TX, *Nematodes* species + TX, streptomycin + TX, streptomycin sesquisulfate + TX, strychnine + TX, methamidophos + TX, sulfadiazine + TX, sulfadiazine sodium salt + TX, dimethomorph + TX, fipronil + TX, thiophanate-methyl + TX, sulfoxide + TX, sulfur + TX, thiophanate-methyl + TX, thiophanate-methyl + TX, tar + TX, t-flumethrin + TX, thiamethoxam + TX, thiamethoxam + TX, TDE + TX, tebuconazole + TX, isobutylethoxyquin + TX, butylpyrimidine + TX, phosmet + TX, dithion + TX, thiamethoxam + TX, tebuconazole + TX, cyclopentylpyrethrin + TX, tert-butylcarbate + TX TX, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]tert-butyl carbamate + TX, Tetrachloroethane + TX, Tetrachlorothiophene + TX, Flufenoxuron + TX, Tetradec-11-en-1-ylacetate + TX, Tetrachlorpyrifos + TX, Tetrafluthrin + TX, Acaricide + TX, Thallium Sulfate + TX, Thiabendazole + TX, Thiafenox + TX, Thiamethoxam + TX, Thiamethoxam + TX, Thifluthrin + TX, Insecticidal + TX, Cyclochlor + TX, Cyclochloroxam Oxalate + TX, Thiamethoxam + TX, Thiamethoxam + TX, Thiammonium Chloride ... TX, Insecticidal + TX, Insecticidal Sodium + TX, Thiaben + TX, Selenopyrethroid + TX, Thiamethoxam + TX, Methyl thiophanate + TX, Trifluthoxycarb + TX, Paramethoprim + TX, Tetrabromopropylate + TX, Permethrin + TX, Tratamide + TX, Triadimefon + TX, Triadimefon + TX, Triadimefon + TX, Azoxystrobin + TX, Benfenthion + TX, Azoxystrobin + TX, Triazophos + TX, Imidazin + TX, Azoxystrobin + TX, Tributyltin Oxide + TX, Isofenphos-3 + TX, Phosphate + TX, Trichogrammae + TX, Chlorpyrifos + TX, Tricyclazole + TX, Tridemorph + TX, Snailicide + TX, Trichloropropoxyphos + Tx, Azoxystrobin + TX, Fluopyram + TX, Azoxystrobin + TX, Mediterranean fruit fly attractant + TX, Mediterranean fruit fly attractant A + TX, Mediterranean fruit fly attractant B1 + TX, Mediterranean fruit fly attractant B2 + TX, Mediterranean fruit fly attractant C + TX, Mixed cypermethrin + TX, Trichloroisocyanuric acid + TX, Anti-rot ester + TX, Triphenyltin acetate +TX, Triphenyltin hydroxide + TX, Tebufenozide + TX, Mefenoxam + TX, Trunc-call + TX, Western Vibrio + TX, Urethroid + TX, Validamycin + TX, Valamidil + TX, Aphid + TX, Mefenoxam + TX, Veratrine + TX, Veratrine + TX, Synergistic Alkyl Ether + TX, Verticillium spp. + TX, Ethylene + TX, Rodenticide + TX, XMC + TX, Xylenol + TX, Zeatin + TX, Zetamethrin + TX, Kasugamycin + TX, Zinc naphthenate + TX, Zinc phosphide + TX, Thiazole zinc + TX, Zineb + ​​TX, Zinc thiram + TX, Azoxystrobin + TX, Benzoylamidol + TX;

[0376] Acinetobacter rumenella + TX, Cladosporium fungi + TX, Cephalosporium + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Cotton brown belt moth granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiodurans strain K84 (Galltrol-A®) + TX, Alternaria + TX, Alternaria cassia + TX, Alternaria destruens (Smolder®) + TX, Powdery mildew (AQ10®) + TX, Aspergillus flavus AF36 (AF36®) + TX, Aspergillus flavus NRRL 21882 (Aflaguard®) + TX, Aspergillus species + TX, Budding bryophytes + TX, Azospirillum (MicroAZ®, TAZO B®) + TX, Azotobacter + TX, Azotobacter chroocuccum (Azotomeal®) + TX, Bionatural Blooming Blossoms® + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinosporus strain AQ746 + TX, Bacillus chitinosporus strain CM-1 + TX, Bacillus circulans + TX, Bacillus sturdier (BioSafe®, BioNem-WP®) especially strain CNMC 1-1582 (e.g., VOTIVO® from BASF) + TX, Bacillus licheniformis strain 3086 (EcoGuard®, Green Releaf®) + TX, Bacillus licheniformis strain HB-2 (Biostart™ formerly known as Rhizoboost®) + TX, Bacillus hempensis + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycosis fungoides strain AQ726 + TX, Bacillus lactis (Milky Spore Powder®) + TX, Bacillus pumilus species + TX, Bacillus pumilus strain AQ717 + TX, Bacillus pumilus strain GB34 (Yield Shield®) + TX, Bacillus pumilus strain QST 2808 (Sonata®, Ballad Plus®) + TX, Bacillus spheroids (VectoLex®) + TX, Bacillus spp. species + TX, Bacillus spp. strain AQ175 + TX, Bacillus spp. strain AQ177 +TX, Bacillus strain AQ178 + TX, Bacillus subtilis strain AQ153 + TX, Bacillus subtilis strain AQ743 + TX, Bacillus subtilis strain QST 713 (CEASE®, Serenade®, Rhapsody®) + TX, Bacillus subtilis strain QST 714 (JAZZ®) + TX, Bacillus subtilis strain QST3002 + TX, Bacillus subtilis strain QST3004 + TX, Bacillus amyloliquefaciens variant strain FZB24 (Taegro®, Rhizopro®) + TX, Bacillus thuringiensis aizawai GC 91 (Agree®) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry1Ab + TX, Bacillus thuringiensis Israel Bacillus thuringiensis (BMP123®, Aquabac®, VectoBac®) + TX, Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bonide®, Scutella WP®, Turilav WP®, Astuto®, Dipel WP®, Biobit®, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensistenebrionis (Novodor®, BtBooster) + TX, Bacillus thuringiensis var. aizawai (XenTari®, DiPel®) + TX, Bacteria spp. (GROWMEND®, GROWSWEET®, Shootup®) + TX, Clavipacter michiganensis bacteriophage (AgriPhage®, Bakflor®) + TX, Beauveria bassiana (Beaugenic®, Brocaril WP®) + TX, Beauveria bassiana GHA (Mycotrol ES®, Mycotrol)O®, BotaniGuard®) + TX, Beauveria brongniartii (Engerlingspilz®, Schweizer Beauveria®, Melocont®) + TX, Beauveria spp. + TX, Botrytis cineria + TX, Bradyrhizobium japonicum (TerraMax®) + TX, Brevibacillus brevis + TX, Burkholderia cepacia (Deny®, Intercept®, Blue Circle®) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp. + TX, Canadian thistle fungus Candida 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®, Biocure®) + TX TX, Candida sake + TX, Candida spp. + TX, Candida tenius + TX, Cediclofenac + TX, Cellulomonas flavigena + TX, Chaetomium* *Cochliodes* (Nova-Cide®) + TX, *Chaetomium globosum* (Nova-Cide®) + TX, *Chromobacterium subtsugae* strain PRAA4-1T (Grandevo®) + TX, *Cladosporium chlorocephalum* + TX, *Cladosporium cladosporioides* + TX, *Cladosporium oxysporum* + TX, *Cladosporium spp.* + TX, *Cladosporium tenuissimum* + TX, *Clonostachys rosea* (EndoFine®) + TX, *Colletotrichum acutatum* + TX, *Coniothyrium minitans* (Cotans WG®) + TX TX, Coniothyrium spp. + TX, Cryptococcus albidus (YIELDPLUS®) + TX, Cryptococcus humicola + TX, Infirmo-miniatus + TX, Cryptococcus laurentii + TX, Cryptoophlebia leucotreta granulovirus (Cryptex®) + TX, Cupriavidus campinensis + TX, Cydia pomonella granulovirus (CYD-X®, Madex®, Madex® Plus, Madex Max, Carpovirusine® + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophthoravirulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum species + TX, Filobasidium floriforme + TX, Fusarium argentis + TX, Fusarium chlamydosporium + TX, Fusaclean®, Biofox C® + TX, Fusarium flocculation + TX, Fusarium species + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum (Primastop®, Prestop®) + TX, Gliocladium roseum + TX, SoilGard® species + TX, Soilgard® + TX, Granupom® + TX, Halobacillus halophilus + TX, Halobacillus litoralis + TX, Halobacillus trueperi + TX, Halomonas species + TX, Halomonas subglaciescola + TX, Halovibrio variabilis + TX, Hansenula polymorpha of grape juice + TX, Helicovex® nucleopolyhedrovirus for cotton bollworm + TX, Gemstar® nucleopolyhedrovirus for corn moth + TX, Cladosporium flavum (formerly known as Paecilomyces flavum strain, PFR-97®, PreFeRal®) + TX, Myconate® isoflavone + TX, Klebsiella citrinum + TX, Klebsiella species + TX, Lagenidium giganteum (Laginex®) + TX, Verticillium lecanii (formerly known as strain KV01 (e.g., Vertalec® of Koppert / Arysta) conidia (Mycotal®) + TX, Lecanicillium longisporum (Vertiblast®) + TX, Lecanicillium muscarium (Vertikil®) + TXTX, Disparvirus® + TX, Halophilic sea cocci + TX, Meira geulakonigii + TX, Destruxin WP® + TX, Met52® + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 (Muscudor®) + TX, Muscodor roseus, especially strain A3-5 (registration number NRRL 30548) + TX, Mycorrhiza species spp. (AMykor®, RootMaximizer®) + TX, *Lycium verrucosum* strain AARC-0255 (DiTera®, BROS PLUS®) + TX, *Ophiostomapiliferum* strain D97 (Sylvanex®) + TX, *Paecilomyces farinosus* + TX, *Paecilomyces lilacinus* strain 251 (MeloCon WG®) + TX, *Paecilomyces lilacinus* (Biostat WP®) + TX, *Bacillus polymyxa* + TX, *BlightBan C9-1®* + TX, *Panthera* species + TX, *Paecilomyces nishizawae*, especially strain Pn1 (from Syngenta / ChemChina's CLARIVA) + TX; *Bacillus* species (Econem®) + TX TX, Penicillium globosum + TX, Penicillium barometz (Jumpstart®, TagTeam®) + TX, Penicillium brevicornum + TX, Penicillium commensalum + TX, Penicillium globosum + TX, Penicillium purpureum + TX, Penicillium species + TX, pure green Penicillium + TX, Rotstop® + TX, Phosphohomeal® phosphate solubilizing bacteria + TX, Phytophthora cryptogea +TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilliermondii + 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, Zequanox® + TX, BlightBan A506® strain of Pseudomonas fluorescens + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp. + TX, Bio-Save® strain of Pseudomonas syringae + TX, Pseudomonas viridiflava + TX, Sporodex L® strain of Pseudozyma flocculosa + TX, Puccinia canaliculata + TX, Wood Warrior® strain of Puccinia thlaspeos + TX, Pythium Paroecandrum + TX, Pythium oligandrum (Polygandron®, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizobia (Dormal®, Vault®) +TX, Rhizoctonia + TX, Rhodococcus globerulus strain AQ719 + TX, Rhodosporidium diobovatum + TX, Rhodosporidium toruloides + TX, Rhodotorula glutinis + TX, Rhodotorula graminis + TX, Rhodotorula mucilagnosa + TX, Rhodotorularubra + TX, Rhodotorula spp. + TX, Saccharomyces cerevisiae + TX, Salinococcus roseus + TX, SARRITOR® + TX, Sclerotinia minor + TX, *Scytalidium* spp. + TX, *Scytalidium uredinicola* + TX, *Serratia marcescens* + TX, *Serratia plymuthica* + TX, *Serratia* spp. + TX, *Sordaria fimicola* + TX, *Spod-X®*, *Spexit®* + TX, *Spodoptera littoralis* nucleopolyhedrovirus (Littovir®) + TX, *Sporobolomyces roseus* + TX, *Stenotrophomonas maltophilia* + TX, *Streptomyces albaduncus* + TX, *Streptomyces exfoliates* + TX, *Streptomyces galbus* + TX, *Streptomyces griseoplanus* + TX, *Streptomyces griseoviridis* (Mycostop®) + TX, *Streptomyces hygroscopicus* +TX, *Streptomyces lydicus* (Actinovate®) + TX, *Streptomyces lydicus* WYEC-108 (ActinoGrow®) + TX, *Streptomyces violaceus* + TX, *Tilletiopsis minor* + TX, *Tilletiopsis* spp. + TX, *Trichoderma asperellum* (T34Biocontrol®) + TX, *Trichoderma atroviride* (Plantmate®) + TX, *Trichoderma gamsii* (Tenet®) + TX, *Trichoderma hamatum* TH 382 + TX, *Trichoderma harzianum rifai* (Mycostar®) + TX, *Trichoderma... Trichoderma harzianum T-22 (Trianum-P®, PlantShield HC®, RootShield®, Tririanum-G®) + TX, Trichoderma harzianum T-39 (Trichodex®) + TX, Trichoderma non-hook (Trichoderma mainhamatum) + TX, Trichoderma koningii + TX, Trichoderma malignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma spp. LC 52 (Sentinel®) + TX, Trichoderma taxi + TX, Trichoderma virens (formerly known as green broom mold GL-21) (SoilGuard®) + TX, Trichoderma virens + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier®) + TX, Trichosporon pullulans + TX, Trichosporon spp. + TX, Trichothecium roseum +TX, Trichothecium spp. + 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 nutrients (Natural II®) + TX, Various fungi (Millennium Microbes®) + TX, Verticillium chlamydosporium + TX, Vip3Aa20 (VIPtera®) + TX, Virgibaclillus marismortui + TX, Xanthomonas campestris pv. Poae (Camperico®) + TX, Burkholderia caudatus + TX, Nematophyte pathogenic bacillus + TX;

[0377] AGNIQUE® MMF + TX, Azadirachtin (Plasma Neem Oil®, AzaGuard®, MeemAzal®, Molt-X®, e.g., AZATIN XL from Certis, Inc.) + TX, Plant IGR (Neemazad®, Neemix®) + TX, BugOil® + TX, Canola Oil (Lilly Miller Vegol®) + TX, Chestnut (Chenopodium ambrosioides near ambrosioides) (Requiem®) + TX, Chrysanthemum Extract (Crisant®) + TX, Lamiaceae Essential Oil (Botania®) + TX, Azadirachtin Oil Extract (Trilogy®) + TX, Clove-Rosemary-Peppermint and Thyme Oil Extract (Garden Insect Killer®) + TX, Garlic + TX, Betaine (Greenstim®) + TX, Kaolin (Screen®) + TX TX, Lemongrass Oil (GreenMatch®) + TX, Tea Tree Oil Extract (also known as Tea Tree Oil) (Timorex Gold®) + TX, Clove-Peppermint-Garlic Oil and Peppermint Blend (Soil Shot®) + TX, Clove-Rosemary and Peppermint Extract Blend (EF 400®) + TX, Rosemary-Sesame-Peppermint-Thyme and Cinnamon Extract Blend (EF 300®) + TX, Neem Oil + TX, Catnip (Nepeta cataria) (Catnip Oil) + TX, Nepeta catarina + TX, Nicotine + TX, Oregano Oil (MossBuster®) + TX, Pedaliaceae Oil (Nematon®) + TX, Pine Oil (Retenol®) + TX, Pyrethrum + TX, Quillaja saponaria (NemaQ®) + TX, Polygonum cuspidatum (Regalia®, Sakalia®) + TX, Rotenone (EcoRoten®) + TX, Rutaceae plant extract (Soleo®) + TX, Soybean oil (Ortho ecosense®) + TX, Brown algae storage glucan (Laminarin®) + TX, Thyme oil + TX;

[0378] (E,Z)-7,9-dodecadien-1-yl acetate + TX, (E,Z,Z)-3,8,11-tetradecanetrienyl acetate + TX, (Z,Z,E)-7,11,13-hexadecanetrienal + TX, 2-methyl-1-butanol + TX, Biolure® + TX, 3M Sprayable Blackheaded Fireworm Pheromone® + TX, Calcium acetate + TX, Check-Mate® + TX, Paramount dispenser-(CM) / Isomate C-Plus® + TX, Entostat powder (extract from palm trees) (Exosex CM®) + TX, Grape leafroller pheromone (3M MEC-GBM Sprayable Pheromone®) + TX, Lavender sensate + TX, Leafroller pheromone (3M MEC – LR) Sprayable Pheromone® + TX, Snip7 Fly Bait® + TX, 3M oriental fruit moth sprayable pheromone® + TX, Peach tree borer pheromone (Isomate-P®) + TX, Scenturion® + TX, Starbar PremiumFly Bait® + TX, Tomato pinworm pheromone (3M Sprayable pheromone®) + TX;

[0379] Acerophagus papaya + TX, Adalia-System® + TX, Adaline® + TX, Aphidalia® + TX, *Aphidalia fasciata* + TX, ... loecki + TX, Citripar® + TX, Red Wax Scale + TX, Golden Wasp + TX, Woodland Flower Bug (Anthocoris nemoralis) (Anthocoris-System®) + TX, Short-spurred Aphid Wasp (Apheline®, Aphiline®) + TX, Short-winged Aphid Wasp + TX, Cotton Aphid Parasitic Wasp (Aphipar®) + TX, Aphelinus-System® + TX, Aphelinus® + TX, Ervipar® + TX, Tobacco Aphid Wasp + TX, Peach Red Aphid Wasp (Aphipar-M®) + TX, Aphidend®, Aphidoline® + TX, Lingnan Yellow Aphid Wasp + TX, Indian and Pakistani Yellow Aphid Wasp + TX, Hassell's Long-tailed Gnatant Wasp + TX TX, Staphyline® + TX, Bumblebee species + TX, Beeline®, Tripol® + TX, Natupol Beehive® + TX, Cephalonomia stephanoderis + TX, Black-backed ladybug + TX, Chrysoline®, Chrysopa® + TX, Red lacewing + TX, Cirrospilus ingenuus + TX, Four-banded serpent wasp + TX, White-spotted orange wasp + TX, Closterocerus chamaeleon + TX, Closterocerus species + TX, Coccidoxenoides perminutus (Planopar®) +TX, *Aphidius chinensis* + TX, *Aphidius lepidopterus* + TX, *Aphidius spp.* + TX, *Aphidius spp.* + TX, *Cryptobug®*, *Cryptoline®* + TX, *Cryptobug spp.* + TX, *Minusa®*, *DacDigline®*, *Minex®* + TX, *Delphastus®* + TX, *Delphastus pusillus* + TX, *Diachasmimorpha krausii* + TX, *Aphidius spp.* + TX, *Diaparsis jucunda* + TX, *Aphidius spp.* + TX, *Diminex®*, *Miglyphus®*, *Digline®* + TX, *Aphidius spp.* species + TX, *Aphidius spp.* + TX, *Encarsia* max®, Encarline®, En-Strip®) + TX, Gondien aphid + TX, Haitian aphid + TX, Syrphidend® + TX, Eretmoceris siphonini + TX, California horned aphid + TX, horned aphid (Enermix®, Ercal®, Eretline e®, Bemimix®) + TX, Haitian horned aphid + TX, Montgomery horned aphid (Bemipar®, Eretline m®) + TX, Eretmocerussiphonini + TX, Four-spotted ladybug + TX, Feltiline® + TX, Spidend® + TX, Alishan leafminer parasitic wasp + TX, Fopius ceratitivorus + TX, WirlessBeehome® + TX, Vespop® + TX, Western Stony Mite + TX, Leystilts scabra + TX, Brachycarpus scabra + TX, HarmoBeetle® + TX, NemaShield HB®, Nemaseek®, Terrane-Nam®, Terrane®, Largenem®, B-Green®, NemAttack®, Nematop® + TX, Nemasys H®, BioNem H®, Exhibitline hm®, Largenem-M® + TX, Lawn Patrol® + TX, Spotted Long-legged Ladybug +TX, Aculeifer-System®, Entomite-A® + TX, Hypoline m®, Entomite-M® + TX, Black Gall Wasp + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Tricolor Flying Wasp + TX, Leptopar® (Orange Scale Parasite) + TX, Longhorn Flying Wasp + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Natufly® (Forked Leaf Greenfly) + TX, Tea-footed Aphid Parasitoide + TX, Mirid Bug (Mirical-N®, Macroline c®, Miral®) + TX, Mesoseiulus longipes + TX, Yellow Broad-stalked Flying Wasp + TX, Metaphycus lounsburyi + TX, Milacewing® + TX, Yellow-winged Flying Wasp + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®) + TX, Neodryinus typhlocybae + TX, Neoseuis californicus + TX, Neoseuis cucumber (THRYPEX®) + TX, Pseudoneoseuis + TX, Nesideocoris tenuis (NesidioBug®, Nesibug®) + TX, Biofly® + TX, Thripor-I®, Oriline i® + TX, Orius laevigatus (Thripor-L®, Oriline l®) + TX, Oriline m® + TX, Thripor-S® + TX, Pauesia juniperorum + TX, Ladybug stalked pygmy wasp + TX, Phasmarhabditishermaphrodita (Nemaslug®) + TX, Phymastichus coffea + TX, Rough-haired phytosei mite + TX, Chilean phytosei mite (Spidex®, Phytoline p®) + TX, Spotted-bellied thorny bug (Podisus®) + TX, Parasitic flea fly curvatus + TX, Parasitic flea fly obtusus + TX, Parasitic flea fly tricuspis + TX, Pseudaphycus maculipennis +TX, Pseudleptomastix mexicana + TX, Psyllid flea wasp + TX, Braconid wasp of the same color (complex) + TX, species of the genus Psyllid wasp + TX, Rhyzobius lophanthae + TX, Australian ladybug + TX, Rumina decollate + TX, Semielacher petiolatus + TX, wheat aphid (Ervibank®) + TX, Steinernema nematode (Nematac C®, Millenium®, BioNem C®, NemAttack®, Nemastar®, Capsanem®) + TX, Steinernema nematode (NemaShield®, Nemasys F®, BioNem F®, Steinernema-System®, NemAttack®, Nemaplus®, Exhibitline sf®, Scia-rid®, Entenem®) + TX, sawfly nematode (Nemasys L®, BioNem) L®, Exhibitline srb®) + TX, BioVector®, BioVektor® + TX, Nematac S® + TX, Species of the genus Nematodes + TX, Species of the family Guardian Nematodes + TX, Stethorus® + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymussinensis + TX, Tricholine b® + TX, Tricho-Strip® + TX, Trichogramma bacillus + TX, Trichogramma spp. ... TX;

[0380] Abscisic acid + TX, Aminomite® + TX, BioGain® + TX, bioSea® + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Collego® + TX, Cueva® + TX, Delta trap (Trapline d®) + TX, Harpin (ProAct®, Ni-HIBIT Gold CST®) + TX, Fatty acids derived from natural byproducts of extra virgin olive oil (FLIPPER®) + TX, Ferromolybdate® + TX, Funnel trap (Trapline y®) + TX, Gallex® + TX, Grower's Secret® + TX, Homo-brassonolide + TX, Ferric phosphate (Lilly Miller Worry Free Ferramol) Slug & Snail Bait® + TX, MCP hail trap (Trapline f®) + TX, parasitic insect Microctonus hyperodae + TX, Mycoleptodiscus terrestris (Des-X®) + TX, locust microsporidia (Semaspore Organic Grasshopper Control®) + TX, pheromone net (Thripline ams®) + TX, potassium bicarbonate (MilStop®) + TX, potassium iodide + potassium thiocyanate (Enzicur®) + TX, potassium salt of fatty acids (Sanova®) + TX, potassium silicate solution (Sil-Matrix®) + TX, spider venom + TX, sticky trap (Trapline YF®, Rebell Amarillo®) + TX, SuffOil-X® + TX, trap (Takitrapline y + b®) + TX TX, Varroa RNA interference agent (vadescana) (CAS No.: 2643947-26-4) + TX;

[0381] Bacillus mojaveii strain R3B (accession number NCAIM (P) B001389) (WO2013 / 034938) from Certis USA + TX, Bacillus pumilus, particularly strain BU F-33, with NRRL accession number 50185 (from BASF's CARTISSA®, EPA accession number 71840-19) + TX, Bacillus subtilis CX-9060 from Certis USA, Bacillus species, particularly strain D747 (available from Kumiai Chemical Industry Co., Ltd. under DOUBLE NICKEL®), with accession number FERM BP-8234, US Patent No. 7,094,592 + TX, Bacillus subtilis strain BU1814 (from BASF's VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA) + TX, Bacillus subtilis variant strain FZB24, with accession number DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA accession number 70127-5)) + TX, Bacillus subtilis, particularly strain QST713 / AQ713 (with NRRL accession number B-21661 and described in US Patent No. 6,060,051, available from Bayer CropScience LP as SERENADE® OPTI or SERENADE® ASO) + TX, Bacillus polymyxa, particularly strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) + TX, Bacillus species, with accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016 / 154297 + TX, Pseudomonas proradix, especially strain E325 (registration number NRRL B-21856) (available from Northwest AgriProducts as BLOOMTIME BIOLOGICAL™ FD BIOPESTICIDE) + TX, Pseudomonas proradix (e.g. PRORADIX® from Sourcon Padena) + TX;

[0382] Budding short-stemmed fungi, especially budding spores of strain DSM14940, budding spores of strain DSM14941, or mixtures of budding spores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, Switzerland) + TX; Pseudozyma aphidis (as disclosed by Yissum Research Development Company, Hebrew University of Jerusalem in WO 2011 / 151819) + TX; Saccharomyces cerevisiae, especially strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 (WO 2010 / 086790) from Lesaffre et Compagnie, France + TX;

[0383] Agrobacterium radialis strain K84 (e.g., GALLTROL-A® from AgBioChem, California) + TX, Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN™ from the University of Pretoria) + TX, Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL registry number B-50768, WO 2014 / 028521) (STARGUS® from Marrone BioInnovations) + TX, Bacillus amyloliquefaciens strain FZB42, registry number DSM 23117 (available from ABiTEP, Germany under RHIZOVITAL®) + TX, Bacillus amyloliquefaciens, particularly strain D747 (available from Combinatorial Chemicals Industries under Double Nickel™, with registry number FERM) BP-8234 (US Patent No. 7,094,592) + TX, Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (from FMC's QUARTZO® (WG) and PRESENCE® (WP)) + TX, Bacillus licheniformis, particularly strain SB3086, with accession number ATCC 55406, WO 2003 / 000051 (available from Novozymes as ECOGUARD® biofungicide and GREEN RELEAF™) + TX, Bacillus methylotrophicus strain BAC-9912 (from the Chinese Academy of Sciences' Institute of Applied Ecology) + TX, Bacillus mycosis fungi, isolate, with accession number B-30890 (available from Certis USA as BMJ TGAI® or WG and LifeGard™) + TX, Bacillus pumilus, particularly strain GB34 (available from Bayer AG, Germany under YieldShield®) + TX, Bacillus pumilus, particularly strain QST2808 (available from Bayer Crop Science, USA under SONATA®, with registration number NRRL B-30087 and described in US Patent No. 6,245,551 (in Chinese) + TX, Bacillus subtilis CX-9060 from Certis USA + TX, Bacillus subtilis IAB / BS03 (AVIV™ from STK Bio-Ag Technologies, PORTENTO® from IdaiNature) + TX, Bacillus subtilis KTSB strain (FOLIACTIVE® from Donaghys) + TX, Bacillus subtilis strain BU1814 (available from BASF AG as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA) + TX, Bacillus subtilis strain GB03 (available from Bayer AG, Germany as Kodiak®) + TX, Bacillus subtilis strain MBI 600 (available from BASF AG as SUBTILEX), with registration number NRRL B-50595, US Patent No. 5,061,495 + TX, Bacillus subtilis strain Y1336 (available from Bion-Tech Ltd., Taiwan under BIOBAC® WP, registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096, and 5277) + TX, Bacillus amyloliquefaciens variant strain FZB24, with registration number DSM 10271 (available from Novozymes under TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) + TX, Bacillus subtilis strain Y1336 (available from Bion-Tech Ltd., Taiwan under BIOBAC® WP, registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096, and 5277) + TX, Epiphytic Bacillus from BASF AG (WO 2016 / 020371) + TX, a *Bacillus polymyxa* plant species from BASF (WO 2016 / 020371) + TX, a *Bacillus* species strain with accession number NRRL B-50972 or NRRL B-67129, WO 2016 / 154297 + TX, *Pseudomonas aeruginosa* strain AFS009 with accession number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER™ and ZIO® from AgBiome Innovations) + TX, *Pseudomonas aeruginosa*, particularly strain MA342 (e.g., CEDOMON®, CERALL®, and CEDRESS® from Bioagri and Koppert) + TX, *Pseudomonas fluorescens* strain A506 (e.g., BLIGHTBAN® from NuFarm). A506) + TX, Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) + TX, Streptomyces glaucusi strain K61 (also known as Streptomyces flavus strain K61) (accession number DSM 7206) (from Verdera's MYCOSTOP®, from BioWorks' PREFENCE®, see Crop Protection 2006, 25, 468-475) + TX, Streptomyces lidystrophy strain WYEC108 (also known as Streptomyces lidystrophy strain WYCD108US) (from Novozymes' ACTINO-IRON® and ACTINOVATE®) + TX;

[0384] Trichoderma viride strain T11 (IMI352941 / CECT20498) + TX, powdery mildew strain AQ10 with registration number CNCM 1-807 (e.g., AQ 10® from IntrachemBio Italia) + TX, powdery mildew, especially strain AQ 10 (e.g., AQ 10® from IntrachemBio Italia) + TX, Aspergillus flavus strain NRRL 21882 (as a known product from Syngenta / ChemChina's AFLA-GUARD®) + TX, budding short-stemmed fungi, especially budding spores of strain DSM 14941 + TX, budding short-stemmed fungi, especially budding spores of strain DSM14940 + TX, budding short-stemmed fungi, especially strains DSM14940 and DSM A mixture of budding spores of 14941 (e.g., Botector® from bio-ferm, Switzerland) + TX, *Chaetomium cupreum* (registration number CABI 353812) (e.g., BIOKUPRUM™ from AgriLife) + TX, *Chaetomium globosum* (available from Rivale under RIVADIOM®) + TX, *Cladosporium cladosporioides*, strain H39, with registration number CBS122244, US 2010 / 0291039 (by Stichting Dienst Landbouwkundig Onderzoek) + TX, *Scutellaria*, particularly strain CON / M / 91-8 (registration number DSM9660, e.g., Contans® from Bayer CropScience Biosciences) + TX, *Cryptococcus* flavescens), strain 3C (NRRL Y-50378) + TX, Dactylariacandida, Dilophosphora alopecuri (available with TWIST FUNGUS®), Fusarium oxysporum, strain Fo47 (available with FUSACLEAN® from Natural Plant Protection) + TX, Alternaria solani (synonym: Alternaria solani) strain J1446 (e.g., Prestop® from Lallemand) + TX,Clonostachys rosea 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'), Australasian Plant Pathol. 2007, 36(2):95-101) + TX, Clonostachys rosea strain ACM941, especially strain 321U from Adjuvants Plus, such as Xue AG (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the roottot complex of field pea [Efficacy of Pink Broom Fungus strain ACM941 and fungicide seed treatment for controlling root rot complex in field peas], Can Jour Plant Sci 2003, 83(3):519-524) disclosed the following strains: Metschnikowia fructicola, especially strain NRRLY-30752 + TX, Microsphaeropsis ochracea, Penicillium steckii from BASF (DSM 27859, WO 2015 / 067800) + TX, Trichoderma strain ICC 012 (also known as Trichoderma harzianum ICC012), with accession number CABI CC IMI 392716 and Trichoderma gesii (formerly Trichoderma viride) strain ICC 080, with accession number IMI 392151 mixture (e.g.,BIO-TAM™ from Isagro USA, Inc. or BIODERMA® from Agrobiosol de Mexico, SA de CV) + TX, Penicillium vermiculatum + TX, Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from Danstar Ferment) + TX, Pseudozyma flocculosa strain PF-A22 UL (available from Plant Products Co., California as SPORODEX® L) + TX, Saccharomyces cerevisiae strain LAS117 cell wall (CEREVISANE® from Lesaffre, ROMEO® from BASF) + TX TX, from Lesaffre Saccharomyces cerevisiae strains CNCM 1-3936, CNCM 1-3937, CNCM 1-3938, CNCM 1-3939 (WO 2010 / 086790) + TX, Saccharomyces cerevisiae, especially strain LASO2 (from Agro-Levures et Dérivés) + TX, *Simplicillium lanosoniveum* + TX, strain T34 (e.g., T34 from Biocontrol Technologies SL, Spain) or strain ICC 012 from ISEG + TX, strain WRL-076 (NRRL Y-30842), US Patent No. 7,579,183 + TX, *Talaromyces flavus*, strain V117b + TX, *Trichoderma asperelloides* JM41R (registration number NRRL) B-50759 (from BASF AG's TRICHO PLUS®) + TX, *Trichoderma echinococcus*, especially strain SKT-1, with registration number FERM P-16510 (e.g., from Combinatorial Chemicals Industries' ECO-HOPE®) + TX, *Trichoderma echinococcus*, especially strain kd (e.g., from Andermatt Biocontrol's T-Gro) + TX, *Trichoderma viride* strain 77B (from Andermatt Biocontrol's T77) + TX, *Trichoderma viride* strain ATCC 20476 (IMI 206040) + TX,Trichoderma LC52 (e.g., Tenet from Agrim Technologies Limited) + TX, Trichoderma LU132 (e.g., Sentinel from Agrim Technologies Limited) + TX, Trichoderma NMI No. V08 / 002388 + TX, Trichoderma NMI No. V08 / 002389 + TX, Trichoderma NMI No. V08 / 002390 + TX, Trichoderma V08 / 002387 + TX, Trichoderma SKT-1 (FERM P-16510), Japanese Patent Application (Kokai) 11-253151 A + TX, Trichoderma SKT-2 (FERM P-16511), Japanese Patent Application (Kokai) 11-253151A + TX, Trichoderma SKT-3 (FERM P-16511) + TX, P-17021), Japanese Patent Application (Kokai Co., Ltd.) 11-253151 A +TX, Trichoderma viride, particularly strain SC1 (registration number CBS 122089, WO 2009 / 116106 and US Patent No. 8,431,120 (from Bi-PA) +TX, Trichoderma viride, strain CNCM 1-1237 (e.g. Esquive® WP from Agrauxine, France) +TX, Trichoderma pygmycin (e.g., TrichoPlus from BASF) +TX, Trichoderma galmus (formerly Trichoderma viride) +TX, Trichoderma galmus (formerly Trichoderma viride) strain ICC 080 (IMICC 392151 CABI) (available from Agriberso Mexico under BIODERMA®) +TX, Trichoderma galmus strain ICC080 (IMI CC 392151) CABI, e.g., BioDerma from Agribairso Mexico + TX, Trichoderma hookeri + TX, Trichoderma hookeri with registration number ATCC 28012 + TX, Trichoderma harzianum + TX, Trichoderma harzianum rifaiT39 (e.g., Trichodex® from Makhteshim, USA) + TX, Trichoderma harzianum strain CepaSimbT5 (from Simbiose Agro) + TX, Trichoderma harzianum strain DB 103 (available from Dagutat Biolab as T-GRO®7456) + TX, Trichoderma harzianum strain ITEM 908 (e.g., Trianum-P from Koppert) + TX, Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) + TX,Trichoderma harzianum strain TH35 (e.g., Root-Pro from Mycontrol) + TX, Trichoderma polysporum strain IMI 206039 (e.g., Binab TF WP from BINAB Bio-Innovation AB, Sweden) + TX, Trichoderma stromaticum with accession number Ts3550 (e.g., Tricovab from CEPLAC, Brazil) + TX, Trichoderma viride (also known as green broom mold) especially strain GL-21 (e.g., SoilGard from Sertis, USA) + TX, Trichoderma viride strain G-41, formerly known as green broom mold (accession number ATCC 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from Bywards, USA) + TX, Trichoderma viride especially strain B35 (Pietr et al., 1993, Zesz.Nauk.AR w Szczecinie 161: 125-137) + TX, *Trichoderma viride* strain TV1 (e.g., *Trianum-P* from Corbert) + TX, *Ulocladium oudemansii* strain U3, with accession number NM 99 / 06216 (e.g., *BOTRY-ZEN®* from Botry-Zen Ltd, New Zealand, and *BOTRYSTOP®* from Bywards) + TX, *Verticillium albo-atrum* (formerly *Verticillium dahliae*) strain WCS850, with accession number WCS850, deposited at the Fungal Culture Centre (e.g., *DUTCH TRIG®* from Tree Care Innovations) + TX, *Verticillium chlamydosporium* + TX;

[0385] A mixture of brown azotobacters and Clostridium pasteurellii (available from Agrinos under INVIGORATE®) + TX; a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC under QUARTZO® (WG) and PRESENCE® (WP)) + TX; *Sinapis latifolia* stem nodule, particularly strain ZB-SK-5 + TX; *Azospirillum brasiliensis* (e.g., VIGOR® from KALO) + TX; *Azospirillum lipophilicus* (e.g., VERTEX-IF™ from TerraMax) + TX; *Azotobacter spheroidae*, particularly strain H23 + TX; brown azotobacters, particularly strain ATCC 12837 + TX; *Bacillus amyloliquefaciens* BS27 (registration number NRRL B-5015) + TX. TX, Bacillus amyloliquefaciens, especially strain FZB42 (e.g., RHIZOVITAL® from Abitep GmbH, Germany) + TX, Bacillus amyloliquefaciens, especially strain IN937a + 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 from Novozymes as QUIKROOTS®) + TX, Bacillus cereus member EE128 (NRRL No. B-50917) + TX, Bacillus cereus member EE349 (NRRL No. B-50928) + TX, Bacillus cereus, especially strain BP01 (ATCC 55675, such as MEPICHLOR® from Arysta Lifescience (USA) + TX, Bacillus mycosis fungoides BT155 (NRRL No. B-50921) + TX, Bacillus mycosis fungoides BT46-3 (NRRL No. B-50922) + TX, Bacillus mycosis fungoides EE118 (NRRL No. B-50918) + TX, Bacillus mycosis fungoides EE141 (NRRL No. B-50916) + TX, Bacillus pumilus, especially strain GB34 (e.g., YIELD SHIELD® from Bayer CropScience, Germany) + TX, Bacillus pumilus, especially strain QST2808 (registration No. B-30087) + TX, Bacillus sicca, especially strain KCTC 13613T + TX. TX, Bacillus subtilis, particularly strain AQ30002 (registration number NRRL B-50421 and described in U.S. Patent Application No. 13 / 330,576) + TX, Bacillus subtilis strain AQ30004 (NRRL No. B-50455 and described in U.S. Patent Application No. 13 / 330,576) + TX, Bacillus subtilis strain MBI 600 (e.g., SUBTILEX® from BASF) + TX, Bacillus subtilis strain rm303 (RHIZOMAX® from Biofilm Crop Protection) + TX, Bacillus subtilis strain BU1814 (available from BASF as TEQUALIS®) + TX, Bacillus tekirae strain NII-0943 + TX, Bacillus thuringiensis BT013A (NRRL No. B-50924), also known as Bacillus thuringiensis 4Q7 + TX, Slow-growing rhizobium of soybean (e.g., OPTIMIZE® from Novozymes) + TX, Delft acidophilus strain RAY209 (e.g., from Brett Young Seeds' BIOBOOST® + TX, Lactobacillus species (e.g., LACTOPLANT® from LactoPAFI) + TX, Meso- and Slow-growing Rhizobia (e.g., NODULATOR from BASF) + TX, Bacillus polymyxa, especially strain AC-1 (e.g., TOPSEED® from Green Biotechnology Ltd.) + TX, Pseudomonas aeruginosa, especially strain PN1 + TX, Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) + TX, Rhizobium leguminosarium biovarviciae (e.g., NODULATOR from BASF) + TX, Rhizobium leguminosarium biovarviciae, especially strain Z25 (CECT 4585) + TX, Serratia marcescens, especially strain SRM (MTCC 8708) + TX TX, *Rhizobium sinense* strain NRG-185-1 (from Bayer Crop Science NITRAGIN® GOLD) + TX, *Thiobacillus* species (e.g., CROPAID® from Cropaid Ltd, UK) + TX;

[0386] Varicella salina strain AARC-0255 (e.g., DiTera™ from Valent Biosciences) + TX, Penicillium baicalensis strain ATCC 22348 (e.g., JumpStart® from Acceleron BioAg) + TX, Penicillium baicalensis strain ATCC ATCC20851 + TX, Paecilomyces lilacinus (formerly known as Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, e.g., BioAct from Bayer CropScience Biosciences) + TX, Pythium oligandrum strain DV74 + TX, Pythium oligandrum strain M1 (ATCC 38472, e.g., Polyversum from Bioprepraty, Czech Republic) + TX TX, *Rhizopogon amylopogon* (from Agri-Enterprise, formerly Myco-Sol of Helena Chemical Company) + TX, *Rhizopogon fulvigleba* (e.g., from Agri-Enterprise, formerly Myco-Sol of Helena Chemical Company) + TX, *Rhizopogon vulgaris* strain V117b + TX, *Trichoderma echinococcus* strain (from Plant Health Products, South Africa, Eco-T) + TX, *Trichoderma echinococcus* strain kd (e.g., T-Gro from Andermart Biocontrol) + TX, *Trichoderma viride*, especially strain number V08 / 002387 + TX, *Trichoderma viride* strain CNCM 1-1237 (e.g., Esquive® WP from Aglaucus, France) + TX, Trichoderma viride strain LC52 (also known as Trichoderma viride strain LU132, e.g., Sentinel from Agrim Technology Ltd.) + TX, Trichoderma viride strain NMI number V08 / 002388 + TX, Trichoderma viride strain NMI number V08 / 002389 + TX, Trichoderma viride strain NMI number V08 / 002390 + TX, Trichoderma viride strain SC1 (described in WO 2009 / 116106) + TX, Trichoderma harzianum strain 1295-22 + TX, Trichoderma harzianum strain ITEM 908 + TX, Trichoderma harzianum strain T-22 (e.g., from Andermatt Biocontrol or Corbett's Trianum-P) + TX, Trichoderma harzianum strain TSTh20 + TX, Trichoderma viride strain GI-3 + TX, Trichoderma viride strain GL-21 (e.g., SoilGard® from Sertex Corporation, USA) + TX,Trichoderma viride strain B35 (Pietr et al., 1993, Zesz.Nauk.AR w Szczecinie161: 125-137) + TX, Verticillium leuciscinum (formerly Verticillium dahliae) strain WCS850 (CBS 276.92, e.g. Dutch Trig from Tree Care Innovations) + TX;

[0387] Agrobacterium radialis strain K84 (Galltrol from Ager Biosciences) + TX, Bacillus amyloliquefaciens, especially strain PTS-4838 (e.g., AVEO from Valencia Biosciences) + TX, Bacillus mycosis fungoides isolate J. (e.g., BmJ from Certis USA) + TX, Bacillus spheroidae, especially serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., VECTOLEX® from Valencia Biosciences) + TX, Bacillus thuringiensis Israel strain BMP 144 (e.g., AQUABAC® from Becker Microbial Products IL, Illinois) + TX, Bacillus thuringiensis subsp. niger strain GC-91 + TX, Bacillus thuringiensis subsp. niger, especially serotype H-7 (e.g., FLORBAC® WG from Valencia Biosciences) + TX TX, Bacillus thuringiensis subsp. niger, especially strain ABTS-1857 (SD-1372, e.g., XENTARI® from Valencia Biosciences) + TX, Bacillus thuringiensis subsp. niger (serotype H-14) strain AM65-52 (accession number ATCC1276) (e.g., VECTOBAC® from Valencia Biosciences) + TX, Bacillus thuringiensis subsp. Kurstak strain ABTS 351 + TX, Bacillus thuringiensis subsp. Kurstak strain BMP 123 (from Becker Microbial Products, Illinois, and BARITONE from Bayer Crop Science) + TX, Bacillus thuringiensis subsp. Kurstak strain EG 2348 (from Certis, Inc., USA) + TX, Bacillus thuringiensis subsp. Kurstak strain EG 7841 (from CRYMAX, Certis, Inc., USA) + TX, Bacillus thuringiensis Kurstak subspecies HD-1 (e.g., DIPEL® ES from Valencia Biosciences, USA) + TX, Bacillus thuringiensis Kurstak subspecies PB 54 + TX, Bacillus thuringiensis Kurstak subspecies SA 11 (JAVELIN from Certis, USA) + TX, Bacillus thuringiensis Kurstak subspecies SA 12 (THURICIDE from Certis, USA) + TX, Bacillus thuringiensis Tenebrionibacterium subspecies NB 176 (SD-5428, e.g., NOVODOR® FC from BioFa DE, Germany) + TX, Bacillus thuringiensis Colmer variant (e.g., TIANBAOBTC from Changzhou Jianghai Chemical Factory) + TX,Bacillus thuringiensis Japanese variant strain Buibui + TX, Bacillus thuringiensis Kurstak variant strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global) + TX, Bacillus laterosporus + TX, Burkholderia species, especially Burkholderia renogeri strain A396 (also known as Burkholderia renogeri strain MBI305) (accession numbers NRRL B-50319, WO 2011 / 106491 and WO 2013 / 032693, e.g., MBI206 TGAI and ZELTO® from Maronni BioInnovation) + TX, Chromobacterium subtsugae, especially strain PRAA4-1T (e.g., MBI-203, e.g., GRANDEVO® from Maronni BioInnovation) + TX. TX, *Scabiei* Ve6 (from MYCOTAL, Corbett) + TX, *Paenibacillus popilliae* (formerly *Bacillus popilliae*, e.g., MILKY SPORE POWDER™ or MILKY SPORE GRANULAR™ from St. Gabriel Laboratories) + TX, *Serratia entomophila* (e.g., INVADE® from Wrightson Seeds) + TX, *Serratia muscaria* strain SRM (accession number MTCC 8708) + TX, *Trichoderma echinococcus* (from TRICHODERMAX, Novozymes) + TX, *Wolbachia pipientis* ZAP strain (e.g., ZAP MALES® from MosquitoMate) + TX;

[0388] Beauveria bassiana strain ATCC 74040 (e.g., NATURALIS® from IntrachemBio Italia) + TX, Beauveria bassiana strain ATP02 (accession number DSM 24665), Apopka 97 (PREFERAL from SePRO) + TX, Beauveria bassiana strain GHA (accession number ATCC74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation) + TX, Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074, disclosed in WO 2017 / 066094, Pioneer Hi-Bred International) + TX, Metarhizium anisopliae Roberts 15013-1 (deposited under NRRL accession number 67073) + TX TX, Metarhizium anisopliae 23013-3 (extracted under NRRL accession number 67075) + TX, Paecilomyces lilacinus strain 251 (from MELOCON, Ceres, Inc., USA) + TX;

[0389] The following viruses were tested: Codling moth (Cydia pomonella) granulovirus (GV) + TX; Cotton bollworm (Helicoverpa armigera) nucleopolyhedrovirus (NPV) + TX; Summer fruit tortrix (Adoxophyes orana) granulovirus (GV) + TX; Beet armyworm (Spodopteraexigua) mNPV + TX; Fall armyworm (Spodoptera frugiperda) mNPV + TX.

[0390] Burkholderia species, especially Burkholderia cepacia (formerly known as Pseudomonas cepacia) + TX, Gigasparora species + TX, Glomus species + TX, Laccaria species + TX, LactoBacillus buchneri + TX, Paraglomus species + TX, Pisolithus tinctorus + TX, Pseudomonas species + TX, Rhizobium species, especially Rhizobium trifolium + TX, Rhizopogon species + TX, Scleroderma species + TX, Streptomyces species + TX, Suillus species spp.) + TX, Agrobacterium spp. + TX, Azorhizobium caulinodans + TX, Azospirillum spp. + TX, Azotobacter spp. + TX, Bradyrhizobium spp. + TX, Gigasparora monosporum + TX;

[0391] Garlic (NEMGUARD from Eco-Spray, BRALIC from ADAMA) + TX, Armour-Zen + TX, Wormwood + TX, Biokeeper WP + TX, Cruciferous extracts, especially rapeseed powder or mustard powder + TX, Cassia nigricans + TX, Bitter orange vine + TX, Chenopodium anthelminticum + TX, Quinoa saponin extract from quinoa seeds (e.g., Heads Up® (quinoa saponins) from Heads Up plant Protectants, Canada) + TX, Chitin + TX, Dryopteris filix-mas + TX, Horsetail + TX, Fortune Aza + TX, Fungastop + TX, Melaleuca alternifolia extract (TIMOREX GOLD from Stockton, STK) + TX TX, naturally occurring blad peptides extracted from lupin seeds (FRACTURE® from FMC) + TX, naturally occurring blad peptides extracted from lupin seeds (PROBLAD® from Sertis Europe) + TX, pyrethroids + TX, Quassia amara + TX, Quercus + TX, soapberry extract (QL AGRI 35 from BASF) + TX, REGALIA MAXX (from Maronni Bio) + TX, Requiem™ insecticide + TX, Reynoutria sachalinensis extract (REGALLIA + TX, ryanodine / rennetine + TX, comfrey + TX, artemisia + 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, Tropaeulum majus + TX, nettle + TX, veratrine + TX, mistletoe + TX;

[0392] Mercuric oxide + TX, octathione + TX, methyl thiophanate + TX;

[0393] MGK 264 + TX, 2-(2-butoxyethoxy)ethyl piperine + TX, 2-isovaleryl indan-1,3-dione + TX, 4-(quinoxalo-2-ylamino)benzenesulfonamide + TX, 5-(1,3-benzo[2-dioxane-5-yl]-3-hexylcyclohex-2-enone + TX, aramaenobenzene + TX, aramaenobenzene-S-methyl + TX, α-bromadiolone + TX, α-chlorool + TX, aluminum phosphide + TX, anthraquinone + TX, antagonist + TX, arsenic trioxide + TX, barium carbonate + TX, chlorpyrifos + TX, dimethomorph + TX, bromadiolone + TX, bromadiolone + TX, bromadiolone + TX, calcium cyanide + TX, chloralose + TX, chlorpyrifos + TX, cholecalciferol + TX, cloquintocet (including cloquintocet-mexyl) + TX, copper naphthenate + TX, copper oxychloride + TX, chlorpyrifos + TX, cyprodinil + TX, cyprodinil + TX, pyrimethanil + TX, cyprodinil + TX, diazinon + TX, allyl oxychloride + TX, dicyclopentadiene + TX, cyprodinil + TX, thiamethoxam + TX, phosmet + TX, calciferol + TX, farnesol + TX, farnesol with nerolidol + TX, fenchlorazole (including fenchlorazole-ethyl) + TX, fenchlordine + TX, flufenoxuron + TX, fluoroacetamide + TX, flufenoxuron + TX, flufenoxuron hydrochloride + TX, flufenoxuron + TX, fenchlordine + TX, γ-HCH + TX, Biguanide Octyl Salt + TX, Biguanide Octyl Acetate + TX, HCH + TX, Hydrogen Cyanide + TX, Imanin + TX, Iodomethyl + TX, Isoxafen (including isoxadifen-ethyl) + TX, Lindane + TX, Magnesium Phosphide + TX, MB-599 + TX, Mefenpyr (including mefenpyr-diethyl) + TX, Mefenpyr Sulfonamide + TX, Cypermethrin + TX, Methyl Bromomethyl + TX, Nerolidol + TX, Sodium Chloride + TX, Petroleum Oil + TX, Ratphosphide + TX, Phosphine + TX, Phosphine + TX, Warfarin + TX, Piperyl Butyl Ether + TX, Synergistic Aldehyde + TX, Potassium Arsenite + TX, Thiamethoxam + TX, Propyl Isomer + TX, pyridine-4-amine + TX, rodenticide + TX, Polygonum cuspidatum extract + TX, ribavirin +TX, S421 + TX, onion glycoside + TX, synergistic powder + TX, sesamin + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoroacetate + TX, strychnine + TX, sulfoxide + TX, thallium sulfate + TX, silane + TX, mixed carbendazim + TX, warfarin + TX, zinc naphthenate + TX, zinc phosphide + TX, zinc thiram + TX.

[0394] References in parentheses following the active ingredient (if present), such as [3878-19-1], refer to Chemical Abstracts Registry Numbers. The mixtures described above are known. In cases where the active ingredient is included in “The Pesticide Manual” [The Pesticide Manual - A World Compendium; 13th Edition; edited by CDS TomLin; The British Crop Protection Council], they are described therein by the entry number given in parentheses above for the specific compound; for example, the compound “avermectin” is described by entry number (1). In cases where “[CCN]” is added above for the specific compound, the compound in question is included in “Compendium of Pesticide Common Names”, which is available on the Internet [A. Wood; Compendium of Pesticide Common Names [Copyright © 1995-2004] obtained; for example, the compound "acetaminophen" is described at the Internet address http: / / www.alanwood.net / pesticides / acetoprole.html middle.

[0395] Most of the active ingredients described above are indicated by what are referred to as “common names” above, with the corresponding “ISO common name” or another “common name” used in different contexts. If the name is not a “common name,” the type of name used is replaced by the name given in parentheses for the specific compound; in this case, the IUPAC name, IUPAC / Chemical Abstracts name, “chemical name,” “traditional name,” “compound name,” or “research code” is used, or if neither of those names nor a “common name” is used, an “alias” is used. “CAS Registry Number” refers to the Chemical Abstracts Registry Number.

[0396] A mixture of compounds of formula (I) selected from those defined in Tables 1 to 4 and Tables P1 to P2 with the active ingredient described above comprises a compound selected from those defined in Tables 1 to 4 and Tables P1 to P2 and the active ingredient described above. These are preferably in a mixing ratio of 100:1 to 1:6000, especially 50:1 to 1:50, more especially in a ratio of 20:1 to 1:20, even more especially 10:1 to 1:10, very especially 5:1 and 1:5, particularly preferably 2:1 to 1:2, and also preferably 4:1 to 2:1, especially 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. The ratios are: 2, 2:1, 1:5, 2:5, 3:5, 4:5, 1:4, 2:4, 3:4, 1:3, 2:3, 1:2, 1:600, 1:300, 1:150, 1:35, 2:35, 4:35, 1:75, 2:75, 4:75, 1:6000, 1:3000, 1:1500, 1:350, 2:350, 4:350, 1:750, 2:750, or 4:750. Those mixing ratios are by weight.

[0397] The mixture described above can be used in methods for controlling pests, excluding methods of treating humans or animals by surgery or therapy, and diagnostic methods performed on humans or animals.

[0398] A mixture of compounds of formula (I) selected from those defined in Tables 1 to 4 and Tables P1 to P2, and one or more active ingredients as described above, can be applied, for example, as a single "ready-to-use" solution, as a combined spray mixture (the mixture being composed of separate formulations of these single active ingredient components, such as "bucket mixes"), and in combination when applied sequentially (i.e., one after another within a moderately short period of time, such as hours or days). The order in which the compounds of formula (I) and the active ingredients as described above are applied is not essential for carrying out the invention.

[0399] The compositions according to the invention may also contain additional solid or liquid adjuvants, such as stabilizers, for example un-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil, or soybean oil), defoamers (e.g., silicone oil), preservatives, viscosity modifiers, binders and / or thickeners, fertilizers, or other active ingredients for achieving specific effects, such as bactericides, fungicides, nematicides, plant activators, molluscicides, or herbicides.

[0400] The compositions according to the invention are prepared in a manner known per se, in the absence of adjuvants, for example by grinding, sieving, and / or compressing solid active ingredients; and in the presence of at least one adjuvant, for example by tightly mixing the active ingredient with one or more adjuvants and / or grinding the active ingredient together with one or more adjuvants. These methods and compounds (I) for preparing the compositions and their uses in preparing these compositions are also the subject of this invention.

[0401] The methods of applying these compositions, i.e., methods for controlling the aforementioned types of pests, such as spraying, atomizing, dusting, brushing, coating, spreading, or irrigating—selected to suit the intended purpose in general circumstances—and the use of these compositions for controlling the aforementioned types of pests are other subjects of the invention. Typical concentration ratios are between 0.1 ppm and 1000 ppm, preferably between 0.1 ppm and 500 ppm of active ingredient. The application rate per metric item is generally 1 to 2000 g of active ingredient per metric item, particularly 10 to 1000 g / ha, preferably 10 to 600 g / ha.

[0402] In the field of crop protection, the preferred method of application is to the leaves of these plants (foliar application), with the frequency and ratio of application likely chosen to match the risk of infection by the pests in question. Alternatively, the active ingredient can reach the plant via the root system (systemic action), by saturating the plant site with a liquid composition, or by introducing the active ingredient in solid form into the plant site (e.g., into the soil, for example, in granular form (soil application)). In the case of rice crops, such granules can be metered and added to the irrigated paddy field.

[0403] The compounds of formula (I) and their compositions of the present invention are also suitable for the protection of plant propagation material (e.g., seeds, fruits, tubers, or grains, or nursery plants) against pests of the types described above. The propagation material can be treated with the compound before planting, for example, seeds can be treated before sowing. Alternatively, the compound can be applied to the seeds by soaking the grains in the liquid composition or by applying a layer of the solid composition (coating). These compositions can also be applied when the propagation material is planted at the application site, for example, by applying the compositions to the seed furrows during row sowing. These methods of treating plant propagation material and the plant propagation material thus treated are further subjects of the present invention. Typical treatment ratios will depend on the plant to be controlled and the pest / fungus, and are generally between 1 and 200 grams per 100 kg of seeds, preferably between 5 and 150 grams per 100 kg of seeds, such as between 10 and 100 grams per 100 kg of seeds.

[0404] The term "seed" includes all kinds of seeds and plant propagules, including but not limited to true seeds, seed tubers, suckers, grains, bulbs, fruits, tubers, cereals, rhizomes, cuttings, cut branches, etc., and in a preferred embodiment refers to true seeds.

[0405] The present invention also includes seeds coated or treated with a compound having Formula I, or seeds containing a compound having Formula I. Although more or less of the ingredient may penetrate into the seed material depending on the method of application, the term "coated or treated with and / or containing" generally indicates that, at the time of application, the active ingredient is, in most cases, on the surface of the seed. When said seed product is (re)planted, it can absorb the active ingredient. In embodiments, the present invention makes it possible to obtain plant propagation material having a compound having Formula I adhered thereto. Furthermore, it makes it possible to obtain compositions comprising plant propagation material treated with a compound having Formula I.

[0406] Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, and seed granulation. Seed treatment with a compound of formula (I) can be applied by any known method, such as spraying or dusting the seeds before sowing or during sowing / planting.

[0407] The compounds of this invention can be distinguished from other similar compounds by their greater efficacy and / or different pest control at lower application rates, which can be achieved by those skilled in the art using experimental procedures with lower concentrations (if necessary), such as 10 ppm, 5 ppm, 2 ppm, 1 ppm, or 0.2 ppm; or lower application rates, such as per m 2The efficacy can be confirmed with 300, 200, or 100 mg AI. Greater efficacy can be observed through increased safety (against non-target organisms such as fish, birds, and bees), improved physicochemical properties, or increased biodegradability.

[0408] In each aspect and embodiment of the invention, “consistently made of” and variations thereof are preferred embodiments of “comprising” and variations thereof, and “consistently made of” and variations thereof are preferred embodiments of “consistently made of” and variations thereof.

[0409] The disclosures in this application make it possible to obtain every combination of the embodiments disclosed herein.

[0410] Biological examples:

[0411] The following examples illustrate the invention. Some compounds of the present invention may differ from known compounds in that they exhibit greater efficacy at lower application rates, which can be demonstrated by those skilled in the art using the experimental procedures outlined in the examples, employing even lower application rates (if necessary), such as 50 ppm, 24 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm, or 0.2 ppm.

[0412] Example B1: Two-spotted spider mite (Tetranychus urticae) mite): Ingestion / Contact Activity

[0413] Bean leaf discs on agar in 24-well microtiter plates were sprayed with an aqueous test solution prepared from a 10,000 ppm DMSO stock solution. After drying, the leaf discs were infected with a mixed-age mite population. The mortality rate of these samples was assessed for the mixed population (active stage) 6 days after infection.

[0414] The following compounds produce a mortality rate of at least 80% at an application rate of 200 ppm:

[0415] P1.1, P1.2, P1.3, P1.4, P1.5, P1.6, P1.7, P1.8, P1.9, P1.10, P1.11, P1.12, P1.13, P1.14, P1.15, P1.16, P1.17, P1.1 8. P1.19, P1.20, P1.21, P1.22, P1.23, P1.24, P1.25, P1.26, P1.27, P1.28, P1.29, P1.30, P1.31, P1.32, P1.33, P2.1.

[0416] Comparison of P1.3 with C1.4 and C1.5

[0417]

[0418] Example B2: Two-spotted spider mite (Tetranychus urticae) mite): Mixed groups, feeding / contact

[0419] One day after infection, French bean plants infected with a mixed-age mite population were sprayed with a diluted test solution in a spray chamber. Larval and adult mortality rates were examined at different concentrations after 1 and 8 days.

[0420] Compound C1.1

[0421]

[0422] Compound P1.1

[0423]

[0424] Compound C1.2

[0425]

[0426] Compound P1.2

[0427]

[0428] Compound C1.4

[0429]

[0430] Compound P1.3

[0431]

[0432] Compound C1.3

[0433]

[0434] Compound P1.4

[0435] .

Claims

1. A compound having formula (I) (I) in R 1 It is ethyl; R 2 It is H or methyl; R 3 It is a C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, or C3-C4-halocycloalkyl; R 4 It is a phenyl group, substituent with 1 to 3 R groups. 5 Substituted phenyl, heteroaryl (which is a 5- or 6-membered monocyclic or a 9- or 10-membered bicyclic), or substituted with 1 to 3 R groups 6 Substituted heteroaryl groups (which are 5 or 6-membered monocyclic or 9 or 10-membered bicyclic). R 5 and R 6 The components are independently selected from halogens, C1-C3-haloalkyl and C1-C3-haloalkoxy; and if the two C1-C3-haloalkoxy groups are substituted on adjacent atoms on the phenyl ring, they can form a 5- or 6-membered ring (e.g., –OC1-C2-haloalkylO-) together with the carbon of the phenyl ring. Or an agriculturally chemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide of the compound having formula (I).

2. The compound according to claim 1, wherein, R 2 It is a methyl group.

3. The compound according to claim 1, wherein, R 2 It is H.

4. The compound according to any one of claims 1 to 3, wherein, R 3 It is methyl, difluoromethyl, trifluoromethyl, or cyclopropyl.

5. The compound according to any one of claims 1 to 4, wherein, R 4 It is a phenyl group substituted with one or two substituents independently selected from chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy and -OCF2-O- groups that form a 5-membered ring with the carbon of the phenyl ring (substituted on adjacent carbon atoms of the phenyl ring).

6. The compound according to claim 1, wherein, R 1 It is ethyl; R 2 It is H; R 3 It is difluoromethyl or trifluoromethyl; and R 4 It is a phenyl group substituted with one or two substituents independently selected from chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy and -OCF2-O- groups that form a 5-membered ring with the carbon of the phenyl ring (substituted on adjacent carbon atoms of the phenyl ring).

7. A composition comprising a compound as defined in any one of claims 1 to 6, one or more adjuvants and diluents, and optionally one or more other active ingredients.

8. A method, which is (i) A method for combating and controlling insects, mites, nematodes, or mollusks, said method comprising applying to the pest, the site of the pest, or plants susceptible to pest attack an effective amount of an insecticidal, acaricidal, nematodeicidal, or molluskic compound as defined in any one of claims 1 to 6 or a composition as defined in claim 7; or (ii) A method for protecting plant propagation material from attack by insects, mites, nematodes, or mollusks, said method comprising treating the propagation material or the site where the propagation material is grown with an effective amount of a compound as defined in any one of claims 1 to 6 or a composition as defined in claim 7; or (iii) A method for controlling parasites inside or on the surface of an animal in need, the method comprising administering an effective amount of a compound as defined in any one of claims 1 to 6 or a composition as defined in claim 7.

9. A plant propagation material, such as a seed, said plant propagation material comprising, or being treated with, said compound or said composition, as defined in any one of claims 1 to 6 or as defined in claim 7, or having said compound or said composition adhered thereto.

10. A compound having the formula Xa X-a Where R 2 and R 3 It is as defined in claim 1.

11. A XI-a compound XI-a Where R 2 and R 3 It is as defined in claim 1, and LG 2 It is chlorine, bromine, or fluorine.

Images