Compounds, method for controlling insects, mites, nematodes or molluscs, insecticidal, acaricidal, nematicidal or molluscidal composition and method of protecting useful plants

Description

COMPOUNDS, METHOD FOR CONTROLLING INSECTS, MITES, NEMATODES OR MOLLUSCS, INSECTICIDAL, ACARICIDAL, NEMATICIDAL OR MOLLUSCIDIC COMPOSITION AND METHOD FOR PROTECTING USEFUL PLANTS (Divided from BR 112016014774-0, filed on 12 / 19 / 2014)

[0001] The present invention relates to bisamide derivatives, to processes and intermediates for the preparation thereof, to methods of using them to control insect, mite, nematode and mollusc pests, and to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising them.

[0002] Compounds with insecticidal properties are known, for example, from WO2008075454, WO08075465 and WO2006137376 (= US2009233962). There is a need for alternative methods of pest control. Preferably, the new compounds may possess improved insecticidal properties, such as improved efficacy, improved selectivity, reduced toxicity, lower tendency to generate resistance, or activity against a wider range of pests. The compounds may be more advantageously formulated or provide more effective distribution and retention at the sites of action, or may be more readily biodegradable.

[0003] It has been surprisingly discovered that certain bisamide derivatives, which are replaced with a specific arylperfluoroalkyl group, have beneficial properties, making them particularly suitable for use as insecticides.

[0004] The present invention therefore provides a compound of formula (I) Petition 870190116135, dated 11 / 11 / 2019, page 11 / 216 2 / 200 (I) Xo is bromine, chlorine, or hydrogen; Xi is methoxy, fluorine, or hydrogen; X2 is selected from hydrogen, a cyano, methoxy, halogen, or methyl group; Yi and Y2 are independently chlorine, bromine, iodine, C1-C4 alkyl groups, C1-C4 haloalkyl groups, C1-C4 alkoxy groups, and C1-C4 haloalkoxy groups; Ri and R2 are independently of each other hydrogen, C1-C8 alkyl groups, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, hydroxyl, C1-C8 alkyloxy, and C1-C4 aminocarbonylalkylene; G1 and G2 are independently of each other oxygen or sulfur; Q represents an optionally substituted aryl group with one to five R3 substituents, which may be the same or different, or a five-membered monocyclic heterocycle containing 1 to 3 independently selected heteroatoms of nitrogen, oxygen, and sulfur, optionally substituted with one to four R3 substituents, which may be the same or different, or a six-membered monocyclic heterocycle containing 1 to 3 independently selected heteroatoms of nitrogen, oxygen, and sulfur, optionally substituted with one to five R3 substituents, which may be the same or different; Petition 870190116135, dated 11 / 11 / 2019, page 12 / 216 3 / 200 Ra is selected from cyano, nitro, halogen, hydroxyl, acetoxy, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxy-C1-C4 alkoxy, C1-C4 CNalkyl, C1-C4-C(O)O alkyl, C1-C4-S(O)2 alkyl, NH2, C1-C4-NH alkyl, (C1-C4UN alkyl, (C1-C4-O)2P(O)O alkyl), phenyl and a five- to six-membered monocyclic heterocycle containing 1 to 3 heteroatoms independently selected from nitrogen, oxygen and sulfur provided that (I) is not 3benzamido-N-[4-[1-[bromo(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-2,6-dimethylphenyl]benzamide or N-[4-[1[bromo(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-2-iodo-6(trifluoromethyl)phenyl]-2-fluoro-3-[(4-fluorobenzoyl)methylamino]benzamide, or an agrochemically acceptable salt or N-oxides thereof.

[0005] The compounds of formula (I) may exist in different geometric or optical isomers (enantiomers and / or diastereomers) or tautomeric forms. This invention encompasses all such isomers and tautomers and their mixtures in all proportions, as well as isotopic forms such as deuterated compounds.

[0006] Compounds of formula I having at least one basic center can form, for example, addition salts of acids, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphorous acid or a hydrohalic acid, with strong organic carboxylic acids, such as C1-C4 alkanecarboxylic acids that are unsubstituted or substituted, for example with Petition 870190116135, dated 11 / 11 / 2019, page 13 / 216 4 / 200 halogens, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as alkane- or aryl-C1-C4 sulfonic acids that are unsubstituted or substituted, for example with halogen, for example methane- or ptoluenesulfonic acid.Compounds of formula I having at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali or alkaline earth metal salts, for example sodium, potassium or magnesium, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a short-chain mono-, di- or trialkylamine, for example ethyl, diethyl, triethyl or dimethylpropylamine, or a short-chain mono-, di- or trihydroxyalkylamine, for example mono-, di- or triethanolamine.

[0007] Alkyl groups occurring in substituent definitions can be linear or branched chains and include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, nonyl, decyl, and their branched isomers. Alkoxy, alkenyl, and alkynyl radicals are derived from the aforementioned alkyl radicals. Alkenyl and alkynyl groups can be mono- or polyunsaturated.

[0008] The halogen is usually fluorine, chlorine, bromine, or iodine. This also applies, correspondingly, to Petition 870190116135, dated 11 / 11 / 2019, page 14 / 216 5 / 200 halogens in combination with other meanings, such as haloalkyls or halophenyls.

[0009] Haloalkyl groups preferably have a chain length of 1 to 6 carbon atoms. A haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

[0010] Alkoxy groups preferably have a preferred chain length of 1 to 4 carbon atoms. Alkoxy groups are, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy; preferably methoxy and ethoxy.

[0011] Haloalkoxy groups preferably have a chain length of 1 to 4 carbon atoms. A haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.

[0012] A heterocycle in the present invention represents a five- to six-membered monocyclic heterocycle containing 1 to 3 independently selected heteroatoms of nitrogen, oxygen, and sulfur, and designates a 5-membered aromatic heterocyclic group or a 5-membered non-aromatic heterocyclic group, or a group Petition 870190116135, dated 11 / 11 / 2019, p. 15 / 216 6 / 200 aromatic heterocyclic group with 6 members or a non-aromatic heterocyclic group with 6 members.

[0013] A 5- or 6-membered heterocyclic group, which may be substituted in the present invention, designates a heterocyclic group in which the hydrogen atom(s) bonded to the carbon atom(s), nitrogen atom(s) and / or sulfur atom(s) is / are optionally substituted by one or more atoms or groups selected from a predefined list, wherein the group has two or more atoms or groups selected from a predefined list, these atoms or groups being the same or different from each other. In the context of an N atom or an S atom, when it oxidizes to form an N-oxide or a sulfone and a sulfoxide respectively, the oxidized analogue is not substituted; however, such an analogue is within the scope of the invention.

[0014] Examples of 5- or 6-membered heterocyclic groups include a pyrrolidine-1-yl group, a tetrahydrofuran-2-yl group, a piperidyl group, a morpholyl group, a thiomorpholyl group, and the like.

[0015] Examples of 5- or 6-membered aromatic heterocyclic groups are 2-pyrrole, the 2-furyl group, 3-furyl, 5-pyrazolyl, 4-pyrazolyl, 1-pyrrole, 2-thienyl, 3-thienyl, imidazol-l-yl, 1,2,4-triazol-l-yl, a 1,2,4-triazol-l-yl group, a 1,2,3,4-tetrazol-l-yl group, a 1,2,3,5-tetrazol-l-yl group, pyrazinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, a 2-pyrimidinyl group, and the like.

[0016] The following list provides settings, including preferred settings, for R1 substitutes, Petition 870190116135, dated 11 / 11 / 2019, p. 16 / 216 7 / 200 R2, R3, Xo, Xi, X2, Yi, Y2, Gi, G2 and Q, with respect to compounds of formula (I). For any of these substituents, any of the definitions shown below may be combined with any definition of any other substituent shown below or elsewhere in this document.

[0017] Preferably, R3 is selected from cyano, nitro, halogen, hydroxyl, acetoxy, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio groups.

[0018] Preferably, G1 and G2 are both oxygen;

[0019] In a preferred embodiment of the invention, Q is a selected group of Q1, Q2, Q3, Q4 and Q5, wherein Q1 is a group of formula (IIa)(W1)n1qi·κ5(IIa) where the W1 substituents are independently selected from hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or haloalkoxy groups. C1-C4, n1 is 0, 1 or 2 Q2 is a formula group (IIb) Q2 = (IIb) where W2 is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, alkoxy groups Petition 870190116135, dated 11 / 11 / 2019, page 17 / 216 8 / 200 C1-C4 or C1-C4 haloalkoxy, Q3 is a formula group (IIc) Q3 = (IIc) where W3 is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy groups, Q4 is a formula group (IId) Q4 = (IId) where W4 is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy groups, Q5 is a group of formula (IIe) / W5Q5= (IIe) where W5 is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy groups.

[0020] In a more preferred embodiment of the invention, Q is a selected group of Q1, Q2, Q3, Q4 and Q5, where Q1 is a formula group (IIa) Q1 = I (IIa) Petition 870190116135, dated 11 / 11 / 2019, p. 18 / 216 9 / 200 where the Wi substituents are cyano groups, and nl is 1; Q2 is a formula group (Ilb) Q2 = (IIb) where W2 is hydrogen; Q3 is a formula group (IIc) (IIc) where W3 is hydrogen; Q4 is a formula group (Ild) Q4 = (IId) where W4 is hydrogen; and Q5 is a formula group (Ile) Q5 = (IIe) where W5 is hydrogen.

[0021] In a preferred embodiment, Q1 is a formula group (IIa)

[0022] In a preferred embodiment, Q2 is a formula group (IIb)

[0023] In a preferred embodiment, Q3 is a group of formula (IIc) Petition 870190116135, dated 11 / 11 / 2019, p. 19 / 216 10 / 200

[0024] In a preferred embodiment, Q4 is a formula group (IId)

[0025] In a preferred embodiment, Q5 is a formula group (IIe)

[0026] In a further preferred embodiment, Yi and Y2 are selected from Cl, Br, I, methyl, ethyl, methoxy, difluoromethoxy, and trifluoromethoxy, Xo is hydrogen or Br or Cl R1 is selected from hydrogen or C1-C2 alkyl groups; R2 is selected from hydrogen, C1-C2 alkyl groups; X1 is methoxy, fluorine, or hydrogen; X2 is hydrogen; G1 and G2 are both oxygen.

[0027] In an even more preferred embodiment, Yi and Y2 are selected from Cl, Br, ethyl, methoxy, and difluoromethoxy; X0 is Br, R1 is selected from hydrogen or C1-C2 alkyl groups; R2 is selected from hydrogen, C1-C2 alkyl groups; X1 is methoxy; X2 is hydrogen; G1 and G2 are both oxygen;

[0028] In another preferred embodiment, Yi and Y2 are selected from Cl, Br, ethyl, methoxy, and difluoromethoxy; X0 is Cl; R1 is selected from hydrogen or alkyl groups. Petition 870190116135, dated 11 / 11 / 2019, page 20 / 216 11 / 200 C1-C2; R2 is selected from hydrogen, C1-C2 alkyl groups; X1 is methoxy; X2 is hydrogen; G1 and G2 are both oxygen;

[0029] In an even more preferred embodiment, Y1 and Y2 are selected from Cl, Br, ethyl, methoxy, and difluoromethoxy; X0 is Br, R1 is selected from hydrogen or C1-C2 alkyl groups; R2 is selected from hydrogen, C1-C2 alkyl groups; X1 is fluorine or hydrogen; X2 is hydrogen; G1 and G2 are both oxygen;

[0030] In another preferred embodiment, Y1 and Y2 are selected from Cl, Br, ethyl, methoxy, and difluoromethoxy; X0 is Cl; R1 is selected from hydrogen or C1-C2 alkyl groups; R2 is selected from hydrogen, C1-C2 alkyl groups; X1 is fluorine or hydrogen; X2 is hydrogen; G1 and G2 are both oxygen.

[0031] In a further preferred embodiment, Y1 and Y2 are selected from Cl, Br, I, methyl, ethyl, methoxy, difluoromethoxy, and trifluoromethoxy, Petition 870190116135, dated 11 / 11 / 2019, page 21 / 216 12 / 200 Xo is hydrogen or Br or Cl Ri is selected from hydrogen or C1-C2 alkyl groups; R2 is selected from hydrogen, C1-C2 alkyl groups; X1 is hydrogen; X2 is hydrogen, a cyano, methoxy, halogen, or methyl group; G1 and G2 are both oxygen;

[0032] In an even more preferred embodiment, Yi and Y2 are selected from Cl, Br, ethyl, methoxy, and difluoromethoxy; X0 is Br, R1 is selected from hydrogen or C1-C2 alkyl groups; R2 is selected from hydrogen, C1-C2 alkyl groups; X1 is hydrogen; X2 is cyan; G1 and G2 are both oxygen;

[0033] In another preferred embodiment, Y1 and Y2 are selected from Cl, Br, ethyl, methoxy, and difluoromethoxy; X0 is Cl; R1 is selected from hydrogen or C1-C2 alkyl groups; R2 is selected from hydrogen, C1-C2 alkyl groups; X1 is hydrogen; X2 is cyan; G1 and G2 are both oxygen; Petition 870190116135, dated 11 / 11 / 2019, page 22 / 216 13 / 200

[0034] In an even more preferred embodiment, Yi and Y2 are selected from Cl, Br, ethyl, methoxy, and difluoromethoxy; Xo is Br, R1 is selected from hydrogen or C1-C2 alkyl groups; R2 is selected from hydrogen, C1-C2 alkyl groups; X1 is hydrogen; X2 is cyan; G1 and G2 are both oxygen;

[0035] In another preferred embodiment, Y1 and Y2 are selected from Cl, Br, ethyl, methoxy, and difluoromethoxy; X0 is Cl; R1 is selected from hydrogen or C1-C2 alkyl groups; R2 is selected from hydrogen, C1-C2 alkyl groups; X1 is hydrogen; X2 is cyan; G1 and G2 are both oxygen;

[0036] In a preferred embodiment, X1 is hydrogen and X2 is CN;

[0037] In another preferred embodiment, X1 is methoxy and X2 is hydrogen;

[0038] In another preferred embodiment of the invention, X1 is fluorine and X2 is H;

[0039] Another aspect of the present invention relates to compounds of formula (III) Petition 870190116135, dated 11 / 11 / 2019, page 23 / 216 14 / 200 (III) wherein Xo, Yi, Y2, Xi, X2, Ri, and R2 are as defined in formula (I), which are useful in the synthesis of compounds according to formula (I).

[0040] The compounds of the invention can be prepared by a variety of methods, for example, by the methods disclosed in WO 08 / 000438 or WO 2010 / 127928. [004i]Compounds of formula (I) can be prepared by treating compounds of formula (IV), wherein R4 is OH, an alkoxy group Ci-Ce, Cl, F or Br, with a compound of formula III, wherein Q, X0, Xi, X2, Yi, Y2, Ri and R2 are as defined for formula I. When R4 is OH, such reactions can be carried out in the presence of a coupling reagent such as DCC (N,N'-dicyclohexylcarbodiimide), EDC (i-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride) or BOP-Cl (bis(2oxo-3-oxazolidinyl)phosphonic chloride), in the presence of a base such as pyridine, triethylamine, 4-(dimethylamino)pyridine or diisopropylethylamine, and optionally in the presence of a nucleophilic catalyst such as hydroxybenzotriazole. When R4 is Cl, such reactions can be carried out under basic conditions, for example in the presence of pyridine, triethylamine, 4-(dimethylamino)pyridine or diisopropylethylamine, and optionally in the presence of a nucleophilic catalyst. Alternatively, it can be Petition 870190116135, dated 11 / 11 / 2019, p. 24 / 216 15 / 200 added a catalytic amount of an iodide salt, for example potassium iodide, to the chloride acid in an inert solvent, such as acetonitrile, to give rise to the product (see for example Organic Letters, 15 (3), pp. 702-705, 2013). Alternatively, the reaction can be carried out in a two-phase system comprising an organic solvent, preferably ethyl acetate, and an aqueous solvent, preferably a sodium bicarbonate solution. When R4 is a C1-C6 alkoxy, the ester can be directly converted to the amide by heating the ester and amine together in a thermal process. (V)

[0042] 1) The compounds of Hydrogen can be prepared from compounds of formula I, wherein X0 is Cl or Br, by catalytic hydrogenation using methods known to those skilled in the art.

[0043] 2) Acid halides of formula (IV), where R4 is Cl, F or Br, can be prepared from carboxylic acids of formula (IV) where R4 is OH, by treatment with thionyl chloride or oxalyl chloride. Petition 870190116135, dated 11 / 11 / 2019, p. 25 / 216 16 / 200

[0044] 3) Carboxylic acids of formula (IV), wherein R4 is OH, can be formed from esters of formula (IV), wherein R4 is a C1-C6 alkoxy group, by treating the ester with an alkaline hydroxide such as sodium hydroxide, in a solvent such as ethanol.

[0045] 4) Esters of formula (IV), wherein R4 is a C1-C6 alkoxy, can be prepared by treating R4a-OH wherein R4a is a C1-C6 alkyl, by acylation with a carboxylic acid of formula Q-COOH or an acid halide of formula Q-COHal, wherein Hal is Cl, F or Br, under standard conditions as described in 1).

[0046] 5) Compounds of formula III can be prepared by forming the N-R2 bond. For example, reductive amination can be achieved by treating amine IIIa with an aldehyde or ketone and a reducing agent such as sodium cyanoborohydride. Alternatively, alkylation can be achieved by treating amine IIIa with an alkylating agent such as an alkyl halide, optionally in the presence of a base. Alternatively, arylation can be achieved by treating the amine with an aryl halide or sulfonate in the presence of a suitable catalyst / ligand system, often a palladium complex (0). Petition 870190116135, dated 11 / 11 / 2019, page 26 / 216 17 / 200

[0047] 6) Compounds with the formula Alkoxy compounds with C1-C6 groups can be prepared from a compound of formula (V), wherein R5 is a C1-C6 alkoxy group and LG is a leaving group, such as bromine, chlorine or sulfonate, by replacing the leaving group with an amine of formula R2-NH2 or another imine analogue, followed by hydrolysis with a metal catalyst. See, for example: Chemical Communications 2009, (14), 1891-1893 or Journal of Organic Chemistry,2000, 65(8), 2612-2614. R5z=\ LGX1 UR2 (V) (VI)

[0048] Compounds of formula (V) and amines of formula R2-NH2 are compounds known or that can be prepared by methods known to those skilled in the art.

[0049] 6a) Alternatively, compounds of formula (VI), where R5 is a C1-C6 alkoxy group, may be Petition 870190116135, dated 11 / 11 / 2019, p. 27 / 216 18 / 200 prepared from compounds of formula VII, wherein R5 is a C1-C1 alkoxy group, by reduction in the presence of a metallic catalyst and a suitable two-carbon building block such as acetaldehyde or acetonitrile. See, for example: J. Org. Chem. 2007, 72, 9815 or Org. Lett. 2005, 7, 471

[0050] 7) Alternatively, compounds of formula (I) can be prepared by treating compounds of formula (III) with a carboxylic acid of formula Q-COOH or an acid halide of formula Q-COHal, wherein Hal is Cl, F or Br, under standard conditions as described in 1). q-co2h or Q-COHal

[0051] 7) Compounds of formula (III) can be formed from compounds of formula (VIII), where P Petition 870190116135, dated 11 / 11 / 2019, p. 28 / 216 19 / 200 is a suitable protecting group and Rg is OH, Cl or a Ci-Cg alkoxy group, by forming an amide linkage with an amine of formula (X) under standard conditions as described in 1), followed by removal of the protecting group P* under standard conditions. Re (IX) Re (VIII) (III)

[0052] 9) Compounds of formula (VIII), where Rg is OH or a C1-C1 alkoxy group, can be prepared by protecting the amine functionality in compounds of formula (IX), where Rg is OH or a C1-C1 alkoxy group. Suitable protecting groups include carbamates (such as tert-butyloxycarbonyl, allyloxycarbonyl and benzyloxycarbonyl), trialkylsilyl groups (such as tert-butyldimethylsilyl) and acyl groups (such as acetyl).

[0053] 10) For compounds of formula (IX) and compounds of formula (VI), the esters, wherein R5 and Rg are Ci-Cg alkoxy groups, can be hydrolyzed to give the acids, wherein R5 and Rg are OH, by treatment with an alkaline hydroxide such as sodium hydroxide, in a solvent such as ethanol. The acids can be converted into the acid chlorides, wherein R5 and Rg are Cl, by treatment with thionyl chloride or oxalyl chloride as described in 2) and 3).

[0054] 11) Alternatively, compounds of formula (VI), where R5 is OH, Cl, F, Br or a C1-Cg alkoxy group, can be directly converted into compounds of formula (III) by forming an amide linkage with an amine of Petition 870190116135, dated 11 / 11 / 2019, p. 29 / 216 20 / 200 formula (X) under standard conditions as described in 1).

[0055] 12) Alternatively, compounds of formula (III) can be prepared from compounds of formula (XII), wherein LG is a leaving group such as iodine, bromine, chlorine or sulfonate, by replacing the leaving group with a compound of formula R2-NH2 or another imine analogue followed by hydrogenolysis with a metal catalyst. See, for example: Chemical Communications (2009), (14), 1891 1893 or Journal of Organic Chemistry (2000), 65(8), 26122614. (XII) (III)

[0056] 13) Compounds of formula (XII) can be prepared from compounds of formula (XI), wherein R7 is Cl or OH and LG is a leaving group as described in 12), by forming an amide linkage under standard conditions as described in 1). Compounds of formula (XI) are known compounds or compounds that can be prepared by methods known to those skilled in the art.

[0057] 14) An alternative synthesis of compounds of formula (IIIb), wherein R2 is hydrogen, can be achieved by reducing nitro compounds of formula (XIII), such as by treatment with tin chloride under acidic conditions, Petition 870190116135, dated 11 / 11 / 2019, p. 30 / 216 21 / 200 or hydrogenation catalyzed by a noble metal such as palladium on carbon.

[0058] 15) Compounds of formula (XIII) can be derived from compounds of formula (XIV), where R7 is OH, Cl or a C1-C6 alkoxy group, by acylation with an amine of formula (X) under standard conditions as described in 1).

[0059] 16) For compounds of formula (XIV), esters in which R7 is a C1-C6 alkoxy group can be hydrolyzed to give acids in which R7 is OH, by treatment with an alkaline hydroxide such as sodium hydroxide, in a solvent such as ethanol as described in 3). The acids can be converted into acid chlorides, where R7 is Cl, by treatment with thionyl chloride or oxalyl chloride as described in 2). Compounds of formula (XIV) are known compounds or compounds that can be prepared by methods known to those skilled in the art.

[0060] 17) Compounds of formula (XIV) where X1 is F (XIVa) can be prepared from a compound of formula (XV) where LG is a leaving group, such as Petition 870190116135, dated 11 / 11 / 2019, p. 31 / 216 22 / 200 diazonium or chloride, by reaction with a fluoride, such as KF.

[0061] The substitution of a halogen with a fluoride nucleophile can also be carried out in intermediates of formula (XIII) in cases where X1 is LG, as defined in compounds of formula (XV).

[0062] 18) Compounds of formula (XIII) where Ri is selected from C1-C5 alkyl groups, C2-C8 alkenyl, C2-C8 alkynyl, can be prepared from compounds of formula (XIII) where Ri is hydrogen, by treating them with a base, followed by an appropriate electrophile. Examples of bases may be metal hydrides, such as sodium hydride, potassium hydride or calcium hydride, or metal alkoxides, such as potassium t-butoxide, or organometals, such as methyllithium, butyllithium, alkylmagnesium halide, metal amides such as lithium diisopropylamide or lithium hexamethyldisylazide, or a basic salt such as potassium carbonate. A solvent may be used. This may be, for example, a polar aprotic solvent such as DMF, or an ether such as THF or dimethoxyethane. The reaction can be carried out below 0 °C or above 80 °C, but preferably in DMF between 0 °C and 25 °C.The electrophile is R2-X', where R2 is selected from C1-C5 alkyl groups, C2-C8 alkenyl groups, C2-C8 alkynyl groups, and X' is a leaving group such as bromide, chloride, iodide, mesylate, triflate, tosylate, and the like. The base can be used in excess as well. Petition 870190116135, dated 11 / 11 / 2019, page 32 / 216 23 / 200 electrophile, but preferably the base is used in equivalent quantities as well as the electrophilic reagent. Base. Ri-X'

[0063] 19) Compounds of formula (I) wherein Q is as defined in the description, R2 is other than hydrogen and R1 is selected from a C1-C5 alkyl group, C2-C8 alkenyl, C2-C8 alkynyl, can be prepared from compound of formula (Ia) wherein Q is as defined in the description, R2 is other than hydrogen and Ri is hydrogen, by treating them with a base, followed by an appropriate electrophile. Examples of bases may be metal hydrides, such as sodium hydride, potassium hydride or calcium hydride, or metal alkoxides, such as potassium t-butoxide, or organometals, such as methyllithium, butyllithium, alkylmagnesium halide, metal amides such as lithium diisopropylamide or lithium hexamethyldisylazide, or a basic salt, such as potassium carbonate. A solvent may be used. This could be, for example, a polar aprotic solvent such as DMF, or an ether such as THF or dimethoxyethane.The reaction can be carried out below 0 °C or above 80 °C, but preferably in DMF between 0 °C and 25 °C. The electrophile is Ri-X', where Ri is selected from C1-C5 alkyl groups, C2-C8 alkenyl, C2-C8 alkynyl and X' is a leaving group such as bromide, chloride, iodide, mesylate, triflate, tosylate and the like. The base can be used in excess, as well as the... Petition 870190116135, dated 11 / 11 / 2019, page 33 / 216 24 / 200 electrophile, but preferably the base is used in equivalent quantities as well as the electrophilic reagent. Preferred conditions are sodium hydride in DMF between 0 (Example: NaH, DMF, Mel) (X' is a leaving group) Base, Ri-X'

[0064] 20) Compounds of formula (I) wherein Q is as defined in the description, R2 is selected from C1-C5 alkyl groups, C2-C8 alkenyl, C2-C8 alkynyl and Ri is other than hydrogen, may be prepared from compound of formula (Ic) wherein Q is as defined in the description, R2 is hydrogen and Ri is other than hydrogen, by treating them with a base, followed by an appropriate electrophile. Examples of bases may be metal hydrides, such as sodium hydride, potassium hydride or calcium hydride, or metal alkoxides, such as potassium t-butoxide, or organometals, such as methyllithium, butyllithium, alkylmagnesium halide, metal amides such as lithium diisopropylamide or lithium hexamethyldisylazide, Petition 870190116135, dated 11 / 11 / 2019, page 34 / 216 25 / 200 or a basic salt, such as potassium carbonate. A solvent may be used. This may be, for example, a polar aprotic solvent such as DMF, or an ether such as THF or dimethoxyethane. The reaction may be carried out below 0 °C or above 80 °C, but preferably in DMF between 0 °C and 25 °C. The electrophile is R2-X', where R2 is selected from C1-C5 alkyl groups, C2-C8 alkenyl, C2-C8 alkynyl and X' is a leaving group such as bromide, chloride, iodide, mesylate, triflate, tosylate and the like. The base may be used in excess as well as the electrophile, but preferably the base is used in equivalent amounts as well as the electrophilic reagent. Preferred conditions are sodium hydride in DMF between 0 °C (Example: NaH, DMF, Mel) (X' is a leaving group) Base, R2-X'

[0065] Compounds of formula I in which Yi, Y2, Ri, Gi, Xi, X2, R2, G2 and Q are as described in formula I, and Xo is hydrogen (i.e., compounds of formula Id), can be obtained from compounds of formula I in which Xo is chlorine or bromine by reduction, for example with a trisPetição 870190116135, dated 11 / 11 / 2019, pág. 35 / 216 26 / 200 (trimethylsilyl)silane, in an inert solvent at temperatures between 30-150 °C, in the presence of an initiating radical such as Azo-bis-(isobutyronitrile), or alternatively with a metal such as iron, in an acidic medium (Bechamp reduction). Reduction, e.g.

[0066] Compounds with formula (X) can be prepared according to the following scheme: Petition 870190116135, dated 11 / 11 / 2019, p. 36 / 216 27 / 200

[0067] In the scheme above, aniline (XVI) is treated with a compound of formula (XIX) (where Xo is bromine and LG is bromide when Xo is chlorine and LG is iodide when Xo is iodide) in a mixture of inert solvents, such as tert-butyl methyl ether and water, in the presence of sodium dithionite at room temperature, in the presence of a phase transfer catalyst (e.g. tetrabutylammonium hydrogen sulfate) to give Petition 870190116135, dated 11 / 11 / 2019, page 37 / 216 28 / 200 compounds of formula XVII. The compounds of formula XVII can be converted into compounds of formula (Xa), wherein Hal is Cl, Br, or I, by treatment with 2 or more equivalents of N-halosucciniamide in a polar aprotic solvent such as dimethylformamide or N-methylpyrolidine at temperatures. The compounds of formula (Xa) thus obtained have the same halogens (chlorine, bromine, or iodine) at positions 2,6 of aniline (Xa). Alternatively, the halogens can be introduced sequentially by treating 1 equivalent of N-halosucciniamide, to give an intermediate of formula (XVIII), which by treatment with another equivalent of N-halosucciniamide leads to compounds of formula (Xa) wherein the halogens at positions 2,6 of (Xa) are different from each other. Alternatively, the compounds of formula X can be prepared as shown in the following scheme: Y2(XVIa)

[0068] In the scheme above, treatment of compounds of formula (XVIa), wherein Yi is a C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, or C1-C4 haloalkoxy group and Y2 is hydrogen or a C1-C4 alkyl group, by treatment with compounds of formula XIX as described above, leads to compounds of formula XVIIa wherein Y1 is a C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, or C1-C4 haloalkoxy group and Y2 is hydrogen or a C1-C4 alkyl group. The compounds of Petition 870190116135, dated 11 / 11 / 2019, p. 38 / 216 29 / 200 formula (XVIIa) in which Y2 is hydrogen, by treatment with N-halosuccinamide as described above, leads to compounds of formula X in which Y1 is a C1-C4 alkyl group, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy and Y2 is Cl, Br, or I. Compounds of formula (XIX) can be prepared according to literature procedures (see Eur. Pat. Appl., 1418163) when LG and Xo are Br, and J. Amer. Chem.

[0069] The compounds according to the invention, namely the compounds of formula (I) and (III), and the compounds mentioned in the method according to the invention, may exist in different geometric or optical isomers, or tautomeric forms.

[0070] This invention covers all such isomers and tautomers and their mixtures in all proportions, as well as isotopic forms such as deuterated compounds.

[0071] The invention also covers salts of all compounds of the invention.

[0072] The compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera, and also other invertebrate pests, for example, mite, nematode and mollusc pests. Insects, mites, nematodes and molluscs are hereinafter collectively referred to as pests. The pests that can be combated and controlled by the use of the compounds of the invention include those pests associated with agriculture (the term includes the cultivation of crops for Petition 870190116135, dated 11 / 11 / 2019, page 39 / 216 30 / 200 food and fibrous products), horticulture and animal husbandry, pets, forestry and the storage of plant-based products (such as fruits, grains and wood); pests associated with damage to man-made structures and the transmission of diseases to humans and animals; and also nuisance pests (such as flies).

[0073] Examples of the animal pests mentioned above are: of the Acarina order, for example, Acalitus spp., Aculus spp., Acaricalus spp., Aceria spp., Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp., Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp., Eotetranychus spp., Eriophyes spp. , Hemitarsonemus spp., Hyalomma spp., Ixodes spp. , Olygonychus spp., Ornithodoros spp., Polyphagotarsone latus, Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp., Polyphagotarsonemus spp., Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp., Tarsonemus spp., and Tetranychus spp.; give order Anoplura, por example Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp., and Phylloxera spp.; give the order Coleoptera, for example Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp., Astylus atromaculatus, Ataenius spp., Atomaria linearis, Chaetocnema tibialis, Cerotoma spp., Conoderus spp., Cosmopolites spp., Cotinis nitida, Curculio spp., Petition 870190116135, dated 11 / 11 / 2019, p. 40 / 216 31 / 200 Cyclocephala spp., Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa ​​decemLineata, Lissorhoptrus spp., Liogenys spp., Maecolaspis spp., Maladera castanea, Megascelis spp., Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Somaticus spp., Sphenophorus spp., Sternechus subsignatus, Tenebrio spp., Tribolium spp., and Trogoderma spp.; give the order Diptera, for example Aedes spp., Anopheles spp., Antherigona soccata, Bactrocea oleae, Bibio hortulanus, Bradysia spp., Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyza tripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis spp., Rivelia quadrifasciata, Scatella spp., Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp., and Tipula spp.; give the order Hemiptera, for example Acanthocoris scabrator, Acrosternum spp., Adelphocoris lineolatus, Amblypelta nitida, Bathycoelia thalassina, Blissus spp., Cimex spp., Clavigralla tomentosicollis, Creontiades spp., Distantiella theobroma, Petition 870190116135, dated 11 / 11 / 2019, p. 41 / 216 32 / 200 Dichelops furcatus, Dysdercus spp., Edessa spp., Euchistus spp., Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus, Leptocorisa spp., Lygus spp., Margarodes spp., Murgantia histrionic, Neomegalotomus spp., Nesidiocoris tenuis, Nezara spp., Nysius simulans, Oebalus insularis, Piesma spp., Piezodorus spp., Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp., Thyanta spp., Triatoma spp., Vatiga illudens; Acyrthosium pisum, Adalges spp., Agalliana ensigera, Agonoscena targionii, Aleurodicus spp., Aleurocanthus spp., Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp., Brachycaudus spp., Brevicoryne brassicae, Cacopsylla spp., Cavariella aegopodii Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp., Cofana spectra, Cryptomyzus spp., Cicadulina spp., Coccus hesperidum, Dalbulus maidis, Dialeurodes spp., Diaphorina citri, Diuraphis noxia, Dysaphis spp., Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp., Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp., Mahanarva spp., Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp., Neotoxoptera spp., Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae,. Petition 870190116135, dated 11 / 11 / 2019, p. 42 / 216 33 / 200 Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp., Phorodon humuli, Phylloxera spp., Planococcus spp., Pseudaulacaspis spp. , Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp. , Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina, Toxoptera spp., Trialeurodes spp., Tridiscus sporoboli, Trionymus spp., Trioza erytreae, Unaspis citri, Zygina flammigera, Zyginidia scutellaris; give the order Hymenoptera, for example Acromyrmex, Arge spp., Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Pogonomyrmex spp., Slenopsis invicta, Solenopsis spp., and Vespa spp.; of the order Isoptera, for example, Coptotermes spp., Corniternes cumulans, Incisitermes spp., Macrotermes spp., Mastotermes spp., Microtermes spp., Reticulitermes spp.; Solenopsis geminate of the order Lepidoptera, for example, Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp., Argyrotaenia spp., Autographa spp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias lesbia, Cosmophila flava, Petition 870190116135, dated 11 / 11 / 2019, p. 43 / 216 34 / 200 Crambus spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp., Eldana saccharina, Ephestia spp., Epinotia spp., Estigmene acrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp., Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp., Noctua spp., Operophtera spp., Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Papaipema nebris, Pectinophora gossypiela, Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Pseudoplusia spp., Rachiplusia nu, Richia albicosta, Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta, and Yponomeuta spp.;. order Mallophaga, for example, Damalinea spp., and Trichodectes spp.; order Orthoptera, for example, Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscus spp., and Schistocerca spp.; give the order Psocoptera, for example, Liposcelis spp.; Petition 870190116135, dated 11 / 11 / 2019, p. 44 / 216 35 / 200 of the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp., and Xenopsylla cheopis; order Thysanoptera, for example, Calliothrips phaseoli, Frankliniella spp. , Heliothrips spp., Hercinothrips spp., Parthenothrips spp., Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp.; of the order Thysanura, for example, Lepisma saccharina.

[0074] The active ingredients according to the invention can be used for the control, that is, containment or destruction, of pests of the above-mentioned type that occur in particular in plants, especially in useful plants and ornamental plants in agriculture, horticulture and forestry, or in organs such as fruits, flowers, foliage, stems, tubers or roots of such plants, and in some cases even plant organs that are formed at a later time remain protected against these pests.

[0075] Suitable target crops are, in particular, cereals such as wheat, barley, rye, oats, rice, maize or sorghum; beet such as sugar beet or fodder beet; fruits, for example pome fruits, stone fruits or soft fruits, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous crops such as beans, lentils, peas or soybeans; oilseed crops such as rapeseed, mustard, poppies, olives, sunflowers, coconuts, castor beans, cocoa or peanuts; cucurbits such as Petition 870190116135, dated 11 / 11 / 2019, p. 45 / 216 36 / 200 pumpkins, cucumbers or melons; fibrous plants such as cotton, flax, hemp or jute; citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or peppers; Lauraceae such as avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, vines, hops, the plantain family, latex plants and ornamental plants.

[0076] The invention therefore provides a method for combating and controlling insects, mites, nematodes or molluscs, comprising applying an effective amount in terms of insecticide, acaricide, nematicide or molluscicide of a compound of formula (I), or a composition containing a compound of formula (I), to a pest, a pest locus, preferably a plant, or a plant susceptible to attack by a pest. The compounds of formula (I) are preferably used against insects, mites or nematodes.

[0077] Regarding mites, for example, Tetranychus cinnabarinus, Tetranychus urticae, Panonychus citri, Aculops pelekassi, Tarsonemus spp..

[0078] Regarding nematodes, for example, Meloidogyne incognita, Bursaphelenchus lignicolus Mamiya et Kiyohara, Aphelenchoides besseyi, Heterodera glycines, Pratylenchus spp. .

[0079] Additionally, the compounds can be used for the control of animal pests, in particular insects, arachnids, helminths, nematodes and mollusks, which are found in agriculture, horticulture, and the surrounding area. Petition 870190116135, dated 11 / 11 / 2019, page 46 / 216 37 / 200 veterinary medicine, in forests, gardens and recreational areas, in the protection of stored products and materials, and in the hygiene sector. They may be preferentially used as plant protection agents. They may be active against normally sensitive and resistant species, and against all or some of the developmental stages.

[0080] These pests include inter alia: From the order Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.. From the class of Arachnida, for example, Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici. Give a class of bivalves, for example, Dreissena spp.. Give the order of Chilopoda, for example, Geophilus spp., Scutigera spp.. From the order Coleoptera, for example, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Petition 870190116135, dated 11 / 11 / 2019, p. 47 / 216 38 / 200 Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp. , Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa ​​decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp. Give the order of Collembola, for example, Onychiurus armed. Give the order of two Dermaptera, for example, the Fork auricularia. Give the order Diplopoda, for example, Blaniulus guttulatus. From the order of Diptera, for example, Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila Petition 870190116135, dated 11 / 11 / 2019, p. 48 / 216 39 / 200 spp. , Fannia spp., Gastrophilus spp., Hylemyia spp. . . Da classe dos Gastropoda, por exemplo, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.. From the class of helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Strongyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.

[0081] Pode ser além do mais possibile controlar protozoários, tais como Eimeria. Give the order of the Heteroptera, for example, the duck Petition 870190116135, dated 11 / 11 / 2019, p. 49 / 216 40 / 200 tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp. Give the order Homoptera, for example, Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp. , Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp. , Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi,. Petition 870190116135, dated 11 / 11 / 2019, page 50 / 216 41 / 200 Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp. , Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastroccus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii. From the order Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.. From the order of Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber. From the order Isoptera, for example, Reticulitermes spp., Odontotermes spp.. From the order Lepidoptera, for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Petition 870190116135, dated 11 / 11 / 2019, page 51 / 216 42 / 200 Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma spp., Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia species. From the order Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria. From the order Siphonaptera, for example, Ceratophyllus spp., Xenopsylla cheopis. From the order Symphyla, for example, Scutigerella immaculata. From the order Thysanoptera, for example, Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.. From the order Thysanura, for example, Lepisma saccharina. Petition 870190116135, dated 11 / 11 / 2019, page 52 / 216 43 / 200

[0082] Phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp. , Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp..

[0083] Furthermore, in the field of veterinary medicine, the new compounds of the present invention can be effectively used against various harmful animal parasitic pests (endoparasites and ectoparasites), for example, insects and helminths.

[0084] Examples of such parasitic animal pests include the pests described below. [0 0 85]Examples of insects include Gasterophilus spp. , Stomoxys spp., Trichodectes spp., Rhodnius spp., Ctenocephalides canis, Cimx lecturius, Ctenocephalides felis, Lucilia cuprina, and the like.

[0086] Examples of mites include Ornithodoros spp., Ixodes spp., Boophilus spp., and similar mites.

[0087] In veterinary areas, e.g., in the field of veterinary medicine, the active compounds according to the present invention are active against animal parasites, in particular ectoparasites or endoparasites.

[0088] The term endoparasites includes in particular helminths such as cestodes, nematodes or trematodes, and protozoa, such as coccidia.

[0089] Ectoparasites are typically and preferentially arthropods, in particular insects such as flies. Petition 870190116135, dated 11 / 11 / 2019, page 53 / 216 44 / 200 (biting and licking insects), parasitic fly larvae, lice, head lice, bird lice, fleas and similar insects; or mites, such as ticks, for example hard-bodied ticks or soft-bodied ticks, or mites, such as scabies mites, crop mites, bird mites and similar insects.

[0090] These parasites include: From the order of Anoplurida, for example Haematopinus spp. , Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; particular examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotes capillatus; from the order of Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp. , Werneckiella spp., Lepikentron spp., Damalina spp. , Trichodectes spp., Felicola spp.; particular examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; give order Diptera e das suborder Nematocerina e Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,. Petition 870190116135, de 11 / 11 / 2019, pág. 54 / 216 45 / 200 Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp. , Oestrus spp., Hypoderma spp., Gasterophilus spp. , Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; particular examples are: Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis, Haematopota italica, Musca autumnalis, Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua,Haematobia stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi, Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca; of the order of Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; particular examples are: Ctenocephalides canis, Petition 870190116135, dated 11 / 11 / 2019, p. 55 / 216 46 / 200 Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. . From the order Blattarida, for example Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp. (e.g., Suppella longipalpa). From the subclass Acari (Acarina) of the orders Meta- and Mesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (the original gene of multi-host ticks), Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; particular examples are: Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum,. Petition 870190116135, dated 11 / 11 / 2019, p. 56 / 216 47 / 200 Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroa jacobsoni; of the order Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.; particular examples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri, Neoschongastia xerothermobia, Trombicula akamushi, Otodectes cynotis, Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae (S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum, Acarapis woodi.

[0091] The active compounds according to the invention are also suitable for controlling arthropods, helminths and protozoa that attack animals.

[0092] Animals include farm livestock such as, for example, cattle, sheep, goats, horses, pigs, Petition 870190116135, dated 11 / 11 / 2019, page 57 / 216 48 / 200 donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey-producing bees.

[0093] Furthermore, animals include domestic animals - also referred to as companion animals - such as, for example, dogs, cats, caged birds, aquarium fish and those known as experimental animals such as, for example, hamsters, guinea pigs, rats and mice.

[0094] By controlling these arthropods, helminths and / or protozoa, the aim is to reduce deaths and improve the performance (in the case of meat, milk, wool, hides, eggs, honey and the like) and health of the host animal, so that it becomes possible to maintain animals more economically and more simply through the use of the active compounds according to the invention.

[0095] For example, it may be desirable to prevent or stop parasites from drawing blood from their hosts.

[0096] Likewise, controlling parasites can help prevent the transmission of infectious agents.

[0097] The term control, as used here in the veterinary field, means that the active compounds are effective in reducing the incidence of the respective parasite in an animal infected with such parasites to harmless levels.

[0098] More specifically, control, as used herein, means that the active compound is effective in killing the respective parasite, inhibiting its growth, or inhibiting its proliferation. Generally, when used for the treatment of animals, the active compounds according Petition 870190116135, dated 11 / 11 / 2019, page 58 / 216 49 / 200 with the invention can be applied directly.

[0099] They are preferably applied as pharmaceutical compositions that may contain pharmaceutically acceptable excipients and / or auxiliaries that are known in the art.

[0100] In the veterinary field and in animal production, the active compounds are applied (e.g., administered) in the manner known as enteral administration in the form of, for example, tablets, capsules, drinks, potions, granules, pastes, boli, by means of nutrition, suppositories; by parenteral administration, such as, for example, by injections (intramuscular, subcutaneous, intravenous, intraperitoneal and similar), implants, by nasal application, by dermal application in the form of, for example, bathing or immersion, spraying, pouring and local application, washing, dusting, and with the aid of configured articles comprising the active compound such as collars, ear tags, tail tags, limb bands, halters, marking devices and the like.

[0101] The active compounds can be formulated as shampoos or as suitable formulations usable in aerosols, non-pressurized sprayers, for example pump sprayers and atomizer sprayers.

[0102] When used for livestock, poultry, domestic animals and the like, the active compounds according to the invention can be applied as formulations (e.g., powders, wettable powders [WP], emulsions, emulsifiable concentrates [EC], fluids, homogeneous solutions, and suspension concentrates [SC]) comprising the active compounds in an amount from 1 to 80 percent Petition 870190116135, dated 11 / 11 / 2019, page 59 / 216 50 / 200 by weight, directly or after dilution (for example, dilution from 100 to 10,000 times), or as a chemical bath.

[0103] When used in the veterinary field, the active compounds according to the invention can be used in combination with synergistic agents or other suitable active compounds, such as, for example, acaricidal, insecticidal, anthelmintic, and antiprotozoal drugs.

[0104] In the present invention, a substance with an insecticidal action against pests including all of these is referred to as an insecticide.

[0105] An active compound of the present invention can be prepared in conventional formulation forms when used as an insecticide.

[0106] Examples of formulation forms include solutions, emulsions, wettable powders, water-dispersible granules, suspensions, powders, foams, pastes, tablets, granules, aerosols, natural and synthetic materials with infiltrated active compound, microcapsules, seed coating agents, formulations used with a combustion apparatus (e.g., cartridges, cans, fumigation coils or similar smoke-generating devices as a combustion apparatus), ULV (cold mist, hot mist), and similar.

[0107] These formulations can be produced by methods that are known per se.

[0108] For example, a formulation may be produced by mixing the active compound with a developing agent, that is, a diluent or liquid vehicle; a liquefied gas diluent or vehicle; a diluent or Petition 870190116135, dated 11 / 11 / 2019, page 60 / 216 51 / 200 solid vehicle, and optionally with a surfactant, i.e., an emulsifying and / or dispersing and / or foaming agent.

[0109] In the case where water is used as a developing agent, for example, an organic solvent may also be used as an auxiliary solvent.

[0110] Examples of the diluent or liquid vehicle include aromatic hydrocarbons (e.g., xylene, toluene, alkylnaphthalene and the like), chlorinated aromatic or aliphatic hydrocarbons (e.g., chlorobenzenes, ethylene chlorides, methylene chlorides), aliphatic hydrocarbons (e.g., cyclohexanes), paraffins (e.g., mineral oil fractions), alcohols (e.g., butanol, glycols and their ethers, esters and the like), ketones (e.g., acetone, methyl and ethyl ketone, methyl and isobutyl ketone, cyclohexanone and the like), strongly polar solvents (e.g., dimethylformamide, dimethyl sulfoxide and the like), water and the like. The diluent or liquefied gas carrier can be those that are gaseous at normal temperature and normal pressure, for example, aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, and halogenated hydrocarbons.Examples of solid diluents include pulverized natural minerals (e.g., kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, and the like), pulverized synthetic minerals (e.g., highly dispersed silicic acid, alumina, silicates, and the like), and similar materials. Examples of solid carriers for granules include pulverized and sieved rocks (e.g., calcite, marble, pumice, sepiolite, dolomite). Petition 870190116135, dated 11 / 11 / 2019, page 61 / 216 52 / 200 and similar), synthetic granules of inorganic and organic powder, fine particles of organic materials (e.g., sawdust, coconut husks, corn cobs, tobacco stems, and similar), and similar. Examples of emulsifying and / or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (e.g., polyglycol alkylaryl ester), alkyl sulfonates, alkyl sulfates, aryl sulfonates, and similar], albumin hydrolysate, and similar. Examples of dispersants include lignin sulfite residual liquor and methylcellulose.

[0111] Fixing agents may also be used in formulations (powders, granules, emulsions), and examples of fixing agents include carboxymethylcellulose, natural and synthetic polymers (e.g., gum arabic, polyvinyl alcohol, polyvinyl acetate, and the like) and the like. Colorants may also be used, and examples of colorants include inorganic pigments (e.g., iron oxide, titanium oxide, Prussian blue and the like), organic colorants such as alizarin dyes, azo dyes or metallic phthalocyanine dyes, and additionally, trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. Formulations may generally contain the active ingredient in an amount ranging from 0.1 to 95 percent by weight, and preferably 0.5 to 90 percent by weight.The compound according to the present invention may also exist as a mixture with other active compounds, for example, insecticides, poison baits, bactericides, miticides, etc. Petition 870190116135, dated 11 / 11 / 2019, page 62 / 216 53 / 200 nematicides, fungicides, growth regulators, herbicides and similar products, in the form of their commercially useful formulations and in application forms prepared from these formulations.

[0112] The content of the compound according to the present invention in a commercially useful application form may vary within a wide range.

[0113] The concentration of the active compound according to the present invention in actual use may be, for example, in the range of 0.0000001 to 100 percent by weight, and preferably 0.00001 to 1 percent by weight.

[0114] The compounds according to the present invention can be used through conventional methods that are appropriate for the form of use.

[0115] The active compound of the present invention, when used against pests that compromise hygiene and pests associated with stored products, has effective stability against alkalis in lime materials, and also shows excellent residual efficacy in wood and soil. The compounds of the invention may have favorable properties regarding the amount applied, residue formulation, selectivity, toxicity, production methodology, high activity, broad spectrum of control, safety, control of resistant organisms, e.g., pests that are resistant to phosphorus agents and / or organic carbamate agents.

[0116] Additional embodiments of the invention are described below.

[0117] Compounds of formula (I) can be used to combat and control infestations of insect pests such as Petition 870190116135, dated 11 / 11 / 2019, page 63 / 216 54 / 200 such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera, and also other invertebrate pests, for example, mite, nematode and mollusk pests. Insects, mites, nematodes and mollusks are hereinafter collectively referred to as pests. The pests that can be combated and controlled by the use of the compounds of the invention include those pests associated with agriculture (the term includes the cultivation of crops for food and fiber products), horticulture and animal husbandry, pets, forestry and the storage of plant products (such as fruits, grains and wood); those pests associated with damage to man-made structures and the transmission of diseases to humans and animals; and also nuisance pests (such as flies).

[0118] The compounds of the invention can be used, for example, on grass, ornamental plants such as flowers, shrubs, deciduous or evergreen trees, for example conifers, as well as for injection into trees, pest management and the like.

[0119] The compounds of the invention can be used to control domestic animal pests including: Ants, Bedbugs (adults), Bees, Beetles, Woodlice, Carpenter Bees, Carpet Beetles, Centipedes, Cicadas, Beetles, Clover Mites, Cockroaches, Confused Meal Weevil, Crickets, Dog Weevils, Earwigs, Fleas, Flies, Smaller Grain Borers, Millipedes, Mosquitoes, Red Meal Beetles, Rice Weevils, Serrated Grain Beetles, Petition 870190116135, dated 11 / 11 / 2019, page 64 / 216 55 / 200 Silverfish, Damp Mealybugs, Spiders, Termites, Ticks, Wasps, Cockroaches, Crickets, Flies, Maca Beetles (such as Darkling, Hide, and Carrion), Mosquitoes, Damp Mealybugs, Scorpions, Spiders, Spider Mites (Two Spot, Spruce), Ticks.

[0120] The compounds of the invention can be used to control pests of ornamental plants including: Ants (Including imported fire ants), Armyworms, Azalea caterpillars, Aphids, Sackworms, Black Vine Weevils (adult), Bordonegundo Stink Bugs, Bud Worms, California Woodworms, Locusts, Cockroaches, Crickets, Cutworms, Oriental Fruithoppers, Elm Chrysomelas, European Hornets, Autumn Spiders, Flea Beetles, Forest Fruithoppers, Hairy Caterpillar larvae, Japanese Beetles (adults), S. Beetles.John (adults), Maple aphids, Leafhoppers, Leaf miners (adults), Cigarette ants, Leaf strippers, Groundflies, Mosquitoes, Oleander moth larvae, Damp scale insects, Pine defoliators, Pine bud beetles, Pine bud moths, Plant bugs, Root weevils, Defoliators, Scale insects (crawling), Spiders, Leafhoppers, Striped beetles, Striped woodworms, Thrips, Shoot moths, Lymanthrid larvae, Wasps, White mites, Brown soft-bodied scale insects, Red California scale insects (crawling), Clover mites, Mealybugs, Pine needle scale insects (crawling) Spider mites, whiteflies.

[0121] The compounds of the invention can be used for Petition 870190116135, dated 11 / 11 / 2019, p. 65 / 216 56 / 200 controls lawn pests including: Ants (including imported Fire Ants), Armyworms, Centipedes, Crickets, Cutworms, Dogworms, Fleas (adult), Grasshoppers, Japanese Beetles (adult), Millipedes, Mites, Mosquitoes (adult), Damp Scale, Lawn Moths, Scale Insects, Ticks (including species that transmit Lyme disease), Meadow Grass Weevils (adult), Black Lawn Ataenius (adult), Chigoe Fleas, Fleas (adult), Larvae (suppression), Hyperodes Weevils (adult), Weevils (nymphs and young adults), Weevils (mature adults), Grass Bugs.

[0122] Examples of pest species that can be controlled by compounds of formula (I) include: Myzus persicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid), Lygus spp. (capsid), Dysdercus spp. (capsid), Nilaparvata lugens (grasshopper), Nephotettix incticeps (cicada), Nezara spp. (true bugs), Euschistus spp. (true bugs), Leptocorisa spp. (true bugs), Frankliniella occidentalis (thrips), Thrips spp. (thrips), Leptinotarsa ​​decemlineata (Colorado potato beetle), Anthonomus grandis (boll weevil), Aonidiella spp. (mealybug), Trialeurodes spp. (whitefly), Bemisia tabaci (whitefly), Ostrinia nubilalis (European corn borer), Spodoptera littoralis (cotton fluke), Heliothis virescens (tobacco worm), Helicoverpa armigera (cotton fluke), Helicoverpa zea (cotton fluke), Sylepta derogata (cotton leafworm), Pieris brassicae (white butterfly), Plutella xylostella (black diamond moth), Agrotis spp.(worm), Chilo suppressalis (borer of. Petition 870190116135, dated 11 / 11 / 2019, page 66 / 216 57 / 200 rice stem), Locusta migratoria (grasshopper), Chortiocetes terminifera (grasshopper), Diabrotica spp. (root worms), Panonychus ulmi (European red mite), Panonychus citri (citrus red mite), Tetranychus urticae (two-spotted spider mite), Tetranychus cinnabarinus (crimson spider mite), Phyllocoptruta oleivora (citrus rust mite), Polyphagotarsonemus latus (large mite), Brevipalpus spp. (flat mites), Boophilus microplus (cattle tick), Dermacentor variabilis (American dog tick), Ctenocephalides felis (cat flea), Liriomyza spp. (leaf miner), Musca domestica (housefly), Aedes aegypti (mosquito), Anopheles spp. (mosquitoes), Culex spp. (mosquitoes), Lucillia spp. (blowflies), Blattella germanica (cockroach), Periplaneta americana (cockroach), Blatta orientalis (cockroach), termites of the Mastotermitidae family (e.g., Mastotermes spp.), of the Kalotermitidae family (e.g., Neotermes spp.)), of the Rhinotermitidae family (e.g., Coptotermes formosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis) and of the Termitidae family (e.g., Globitermes sulphureus), Solenopsis geminata (fire ant), Monomorium pharaonis (pharaoh ant), Damalinia spp. and Linognathus spp. (biting and sucking lice), Meloidogyne spp. (root-node nematodes), Globodera spp. and Heterodera spp. (cyst nematodes), Pratylenchus spp. (lesion nematodes), Rhodopholus spp. (banana nematodes), Tylenchulus spp. (citrus nematodes), Haemonchus contortus (worm), Caenorhabditis elegans (golden nematode), Trichostrongylus spp. (gastrointestinal nematodes) and Deroceras reticulatum. Petition 870190116135, dated 11 / 11 / 2019, page 67 / 216 58 / 200 (slugs).

[0123] The compounds of the invention can be used for pest control in various plants, including soybeans (e.g., in some cases 10-70 g / ha), corn (e.g., in some cases 10-70 g / ha), sugarcane (e.g., in some cases 20-200 g / ha), alfalfa (e.g., in some cases 10-70 g / ha), brassicas (e.g., in some cases 10-50 g / ha), rapeseed (e.g., canola) (e.g., in some cases 20-70 g / ha), potatoes (including sweet potatoes) (e.g., in some cases 10-70 g / ha), cotton (e.g., in some cases 10-70 g / ha), rice (e.g., in some cases 10-70 g / ha), coffee (e.g., in some cases 30-150 g / ha), citrus fruits (e.g., in some cases 60-200 g / ha), almonds (e.g., in some cases 40-180 g / ha), vegetables (e.g., tomatoes, bell peppers, chili peppers, eggplant, cucumber, pumpkin, etc.).) (e.g., in some cases 10-80 g / ha), tea (e.g., in some cases 20-150 g / ha), bulb vegetables (e.g., onions, leeks, etc.) (e.g., in some cases 30-90 g / ha), grapes (e.g., in some cases 30-180 g / ha), pomes (e.g., apples, pears, etc.) (e.g., in some cases 30-180 g / ha), and stone fruit (e.g., pears, plums, etc.) (e.g., in some cases 30-180 g / ha).

[0124] The compounds of the invention can be used in soybeans to control, for example, Elasmopalpus lignosellus, Diloboderus abderus, Diabrotica speciosa, Sternechus subsignatus, Formicidae, Agrotis ypsilon, Julus spp., Anticarsia gemmatalis, Megascelis spp., Procornitermes spp., Gryllotalpidae, Nezara viridula, Piezodorus spp., Petition 870190116135, dated 11 / 11 / 2019, page 68 / 216 59 / 200 Acrosternum spp., Neomegalotomus spp., Cerotoma trifurcata, Popillia japonica, Edessa spp., Liogenys fuscus, Euchistus heros, stalk borer, Scaptocoris castanea, phyllophaga spp., Pseudoplusia includens, Spodoptera spp., Bemisia tabaci, Agriotes spp.. The compounds of the invention are preferably used in soybean to control Diloboderus abderus, Diabrotica speciosa, Nezara viridula, Piezodorus spp., Acrosternum spp., Cerotoma trifurcata, Popillia japonica, Euchistus heros, phyllophaga spp., Agriotes spp..

[0125] The compounds of the invention can be used in corn to control, for example, Euchistus heros, Dichelops furcatus, Diloboderus abderus, Elasmopalpus lignosellus, Spodoptera frugiperda, Nezara viridula, Cerotoma trifurcata, Popillia japonica, Agrotis ypsilon, Diabrotica speciosa, Heteroptera, Procornitermes ssp., Scaptocoris castanea, Formicidae, Julus ssp., Dalbulus maidis, Diabrotica virgifera, Mocis latipes, Bemisia tabaci, heliothis spp., Tetranychus spp., Thrips spp., phyllophaga spp., scaptocoris spp., Liogenys fuscus, Spodoptera spp., Ostrinia spp., Sesamia spp., Agriotes spp. The compounds of the invention are preferably used in corn to control Euchistus heros, Dichelops furcatus, Diloboderus abderus, Nezara viridula, Cerotoma trifurcata, Popillia japonica, Diabrotica speciosa, Diabrotica virgifera, Tetranychus spp., Thrips spp., Phyllophaga spp., Scaptocoris spp., Agriotes spp.

[0126] The compounds of the invention can be used in sugarcane to control, for example, Sphenophorus spp., termites, Mahanarva spp. The compounds of the invention are preferably used in sugarcane to Petition 870190116135, dated 11 / 11 / 2019, page 69 / 216 60 / 200 control termites, Mahanarva spp.

[0127] The compounds of the invention can be used in alfalfa to control, for example, Hypera brunneipennis, Hypera postica, Colias eurytheme, Collops spp., Empoasca solana, Epitrix, Geocoris spp., Lygus hesperus, Lygus lineolaris, Spissistilus spp., Spodoptera spp., Trichoplusia ni. The compounds of the invention are preferably used on alfalfa to control Hypera brunneipennis, Hypera postica, Empoasca solana, Epitrix, Lygus hesperus, Lygus lineolaris, Trichoplusia ni.

[0128] The compounds of the invention can be used in brassicas to control, for example, Plutella xylostella, Pieris spp., Mamestra spp., Plusia spp., Trichoplusia ni, Phyllotreta spp., Spodoptera spp., Empoasca solana, Thrips spp., Spodoptera spp., Delia spp.. The compounds of the invention are preferably used in brassicas to control Plutella xylostella, Pieris spp., Plusia spp., Trichoplusia ni, Phyllotreta spp., Thrips spp..

[0129] The compounds of the invention can be used in rapeseed, e.g., canola, to control, for example, Meligethes spp., Ceutorhynchus napi, Psylloides spp..

[0130] The compounds of the invention can be used in potatoes, including sweet potatoes, to control, for example, Empoasca spp., Leptinotarsa ​​spp., Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Maladera matrida, Agriotes spp.. The compounds of the invention are preferably used in potatoes, including sweet potatoes, to control Empoasca spp., Leptinotarsa ​​spp., Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Agriotes spp.. Petition 870190116135, dated 11 / 11 / 2019, page 70 / 216 61 / 200

[0131] The compounds of the invention can be used in cotton to control, for example, Anthonomus grandis, Pectinophora spp., Heliothis spp., Spodoptera spp., Tetranychus spp., Empoasca spp., Thrips spp., Bemisia tabaci, Lygus spp., Phyllophaga spp., Scaptocoris spp.. The compounds of the invention are preferably used in cotton to control Anthonomus grandis, Tetranychus spp., Empoasca spp., Thrips spp., Lygus spp., Phyllophaga spp., Scaptocoris spp..

[0132] The compounds of the invention can be used in rice to control, for example, Leptocorisa spp., Cnaphalocrosis spp., Chilo spp., Scirpophaga spp., Lissorhoptrus spp., Oebalus pugnax. The compounds of the invention are preferably used in rice to control Leptocorisa spp., Lissorhoptrus spp., Oebalus pugnax.

[0133] The compounds of the invention can be used in coffee to control, for example, Hypothenemus Hampei, Perileucoptera Coffeella, Tetranychus spp.. The compounds of the invention are preferably used in coffee to control Hypothenemus Hampei, Perileucoptera Coffeella.

[0134] The compounds of the invention can be used in citrus to control, for example, Panonychus citri, Phyllocoptruta oleivora, Brevipalpus spp., Diaphorina citri, Scirtothrips spp., Thrips spp., Unaspis spp., Ceratitis capitata, Phyllocnistis spp.. The compounds of the invention are preferably used in citrus to control Panonychus citri, Phyllocoptruta oleivora, Brevipalpus spp., Diaphorina citri, Scirtothrips spp., Thrips spp., Phyllocnistis spp.. Petition 870190116135, dated 11 / 11 / 2019, page 71 / 216 62 / 200

[0135] The compounds of the invention can be used in almonds to control, for example, Amyelois transitella, Tetranychus spp..

[0136] The compounds of the invention can be used on fruits and vegetables, including tomatoes, peppers, chili peppers, eggplant, cucumbers, pumpkins, etc., to control Thrips spp, Tetranychus spp., Polyphagotarsonemus spp., Aculops spp., Empoasca spp., Spodoptera spp., Heliothis spp., Tuta absoluta, Liriomyza spp., Bemisia tabaci, Trialeurodes spp., Paratrioza spp., Frankliniella occidentalis, Frankliniella spp., Anthonomus spp. The compounds of the invention are preferably used in fruits and vegetables, including tomatoes, peppers, chili peppers, eggplant, cucumber, pumpkin, etc., to control, for example, Thrips spp., Tetranychus spp., Polyphagotarsonemus spp., Aculops spp., Empoasca spp., Spodoptera spp., Heliothis spp., Tuta absoluta, Liriomyza spp., Paratrioza spp., Frankliniella occidentalis, Frankliniella spp., Amrasca spp., Scirtothrips spp., Leucinodes spp., Neoleucinodes spp.

[0137] The compounds of the invention can be used in tea to control, for example, Pseudaulacaspis spp., Empoasca spp., Scirtothrips spp., Caloptilia theivora. The compounds of the invention are preferably used in tea to control Empoasca spp., Scirtothrips spp..

[0138] The compounds of the invention can be used on bulb vegetables, including onions, leeks, etc., to control, for example, Thrips spp., Spodoptera spp., Petition 870190116135, dated 11 / 11 / 2019, p. 72 / 216 63 / 200 Heliothis spp. The compounds of the invention are preferably used in bulb vegetables, including onions, leeks, etc., to control Thrips spp.

[0139] The compounds of the invention can be used in grapes to control, for example, Empoasca spp., Lobesia spp., Frankliniella spp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus, Eotetranychus Willamettei, Erythroneura Elegantula, Scaphoides spp. The compounds of the invention are preferably used in grapes to control Frankliniella spp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus, Scaphoides spp.

[0140] The compounds of the invention can be used on pome fruits, including apples, pears, etc., to control, for example, Cacopsylla spp., Psylla spp., Panonychus ulmi, Cydia pomonella. The compounds of the invention are preferably used on pome fruits, including apples, pears, etc., to control Cacopsylla spp., Psylla spp., Panonychus ulmi.

[0141] The compounds of the invention can be used on stone fruits to control, for example, Grapholita molesta, Scirtothrips spp., Thrips spp., Frankliniella spp., Tetranychus spp. The compounds of the invention are preferably used on stone fruits to control Scirtothrips spp., Thrips spp., Frankliniella spp., Tetranychus spp. The invention therefore provides a method for combating and / or controlling an animal pest, e.g., an invertebrate animal pest, comprising applying to the pest, to a locus of the pest, or to a plant susceptible to attack by the pest, an effective quantity in pesticidal terms of a compound of formula (I). In Petition 870190116135, dated 11 / 11 / 2019, page 73 / 216 64 / 200 in particular, the invention provides a method for combating and / or controlling insects, mites, nematodes or molluscs comprising applying an effective amount in terms of insecticide, acaricide, nematicide or molluscicide of a compound of formula (I), or of a composition containing a compound of formula (I), to a pest, a pest locus, preferably a plant, or to a plant susceptible to attack by a pest. The compounds of formula (I) are preferably used against insects, mites or nematodes.

[0142] The term plant, as used herein, includes seedlings, shrubs and trees. Crops are to be understood as also including those crops that have been made tolerant to herbicides or classes of herbicides (e.g., ALS, GS, EPSPS, PPO and HPPD inhibitors) by conventional breeding or genetic engineering methods. An example of a crop that has been made tolerant to imidazolinones, e.g., imazamox, by conventional breeding methods is Clearfield® summer rapeseed (canola). Examples of crops that have been made herbicide-tolerant by genetic engineering methods include, e.g., glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®.

[0143] Crops are also to be understood as those that have been made resistant to harmful insects by genetic engineering methods, for example Bt corn (resistant to the European corn borer), Bt cotton (resistant to the boll weevil) and also Bt potatoes (resistant to the Colorado potato beetle). Examples Petition 870190116135, dated 11 / 11 / 2019, page 74 / 216 65 / 200 Bt corn hybrids are the Bt 176 corn hybrids from NK® (Syngenta Seeds). Examples of transgenic plants comprising one or more genes encoding insecticide resistance and expressing one or more toxins are KnockOut® (corn), Yield Gard® (corn), NuCOTIN33B® (cotton), Bollgard® (cotton), Newleaf® (potatoes), NatureGard®, and Protexcta®. Plant crops or their seed material may be herbicide-resistant and simultaneously resistant to insect feeding (stacked transgenic events). For example, seeds may have the ability to express an insecticidal Cry3 protein while simultaneously being tolerant to glyphosate.

[0144] Crops are also to be understood as those that are obtained by conventional breeding or genetic engineering methods, and that contain the so-called production characteristics (e.g., improved stability in storage, higher nutritional value and improved flavor).

[0145] In order to apply a compound of formula (I) as an insecticide, acaricide, nematicide or molluscicide to a pest, a pest locus, or a plant susceptible to attack by a pest, a compound of formula (I) is usually formulated in a composition that includes, in addition to the compound of formula (I), a suitable diluent or inert vehicle and, optionally, a surfactant (SFA). SFAs are chemical compounds capable of modifying the properties of an interface (e.g., liquid / solid, liquid / air or liquid / liquid interfaces) by decreasing the interfacial tension and thus leading to changes in other properties (e.g., dispersion, Petition 870190116135, dated 11 / 11 / 2019, page 75 / 216 66 / 200 emulsification and wetting). It is preferred that all compositions (solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60% of a compound of formula (I). The composition is generally used for pest control, such that a compound of formula (I) is applied at a rate of 0.1 ga 10 kg per hectare, preferably 1 ga 6 kg per hectare, more preferably 1 ga 1 kg per hectare.

[0146] When used in a seed coating, a compound of formula (I) is generally used at a rate of 0.0001 ga 10 g (e.g., 0.001 g or 0.05 g), preferably 0.005 ga 10 g, more preferably 0.005 ga 4 g, per kilogram of seeds.

[0147] In another aspect, the present invention provides a composition comprising an effective pesticidal amount of a compound of formula (I), in particular an insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an effective insecticidal, acaricidal, nematicidal or molluscicidal amount of a compound of formula (I) and a suitable carrier or diluent therefor. The composition is preferably an insecticidal, acaricidal, nematicidal or molluscicidal composition.

[0148] Compositions can be selected from a number of formulation types, including dustable powders (DP), soluble powders (SP), water-soluble granules (SG), water-dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil-miscible liquids (OL), bulk liquids Petition 870190116135, dated 11 / 11 / 2019, page 76 / 216 67 / 200 ultra-low (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil-in-water (EW) and water-in-oil (EO)), microemulsions (ME), suspension concentrates (SC), aerosols, misting / fumigation formulations, capsule suspensions (CS) and seed treatment formulations. The type of formulation chosen in any case will depend on the particular intended purpose and the physical, chemical and biological properties of the compound of formula (I).

[0149] Pulverizable powders (PP) can be prepared by mixing a compound of formula (I) with one or more solid diluents (for example, natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earth, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture into a fine powder.

[0150] Soluble powders (SP) can be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve dispersibility / solubility in water. The mixture is then ground to a fine powder. Similar compositions can also be granulated to form water-soluble granules (GS).

[0151] Wettable powders (WP) can be prepared by Petition 870190116135, dated 11 / 11 / 2019, page 77 / 216 68 / 200 mixture of a compound of formula (I) with one or more diluents or solid carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate dispersion in liquids. The mixture is then ground into a fine powder. Similar compositions may also be granulated to form water-dispersible granules (WG).

[0152] The granules (GR) can be formed by granulating a mixture of a compound of formula (I) and one or more solid powder diluents or carriers, or from blank granules pre-formed by absorption of a compound of formula (I) (or a solution thereof, in a suitable agent) into a porous granular material (such as pumice, attapulgite clays, Fuller's earth, kieselguhr, diatomaceous earth or crushed corn cobs) or by adsorption of a compound of formula (I) (or a solution thereof, in a suitable agent) onto a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary. Agents that are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones, and esters) and adhesive agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars, and vegetable oils).One or more other additives may also be included in granules (for example, an emulsifying agent, wetting agent or dispersing agent).

[0153] Dispersible Concentrates (DC) can be prepared by dissolving a compound of formula (I) in Petition 870190116135, dated 11 / 11 / 2019, page 78 / 216 69 / 200 water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surfactant (for example to improve dilution in water or to prevent crystallization in a spray tank).

[0154] Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) can be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in EC include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trademark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidones or N-octylpyrrolidones), dimethyl amides of fatty acids (such as C8-C10 dimethylamide of fatty acids) and chlorinated hydrocarbons.An EC product can emulsify spontaneously upon addition to water, so as to produce an emulsion with sufficient stability to permit spray application using appropriate equipment. The preparation of an EW involves obtaining a compound of formula (I) in the form of a liquid (if not a liquid at room temperature, it can be melted at a reasonable temperature, typically below 70 °C) or in solution (by dissolving it in a suitable solvent) and then emulsifying the resulting liquid or solution in water containing one or more SFAs, under high conditions. Petition 870190116135, dated 11 / 11 / 2019, page 79 / 216 70 / 200 shear, to produce an emulsion. Suitable solvents for use in EW include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other suitable organic solvents that have low solubility in water.

[0155] Microemulsions (ME) can be prepared by mixing water with a mixture of one or more solvents with one or more SFAs to spontaneously produce a thermodynamically stable isotropic liquid formulation. A compound of formula (I) is initially present in the water or in the solvent / SFA combination. Suitable solvents for use in ME include those previously described herein for use in EC or EW. An ME can be an oil-in-water or water-in-oil system (the system present can be determined by conductivity measurements), and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. An ME is suitable for dilution in water, remaining as a microemulsion or forming a conventional oil-in-water emulsion.

[0156] Suspended concentrates (SCs) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I). SCs may be prepared by grinding the solid compound of formula (I) in a ball or spherule mill in a suitable medium, optionally with one or more dispersing agents, to produce a suspension of fine particles of the compound. One or more wetting agents and a suspending agent may be included in the composition to reduce the rate at which the particles Petition 870190116135, dated 11 / 11 / 2019, p. 80 / 216 71 / 200 sediment. Alternatively, a compound of formula (I) can be dry-ground and added to water containing the agents described herein above to prepare the desired final product.

[0157] The aerosol formulations comprise a compound of formula (I) and a suitable propellant (e.g., n-butane). A compound of formula (I) may also be dissolved or dispersed in a suitable medium (e.g., water or a water-miscible liquid such as n-propanol) to provide compositions for use in non-pressurized, hand-held spray pumps.

[0158] A compound of formula (I) can be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.

[0159] Capsule suspensions (CS) can be prepared in a similar manner to the preparation of EW formulations, but with an additional polymerization step such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (I) and, optionally, a vehicle or diluent for the same. The polymeric shell can be produced by an interfacial polycondensation reaction or by a coacervation procedure. The compositions can provide controlled release of the compound of formula (I) and can be used for seed treatment. A compound of formula (I) can also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound. Petition 870190116135, dated 11 / 11 / 2019, page 81 / 216 72 / 200

[0160] A composition may include one or more additives to improve the biological performance of the composition (for example, by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula (I)). Such additives include surfactants, oil-based spray additives, for example certain mineral oils or natural vegetable oils (such as soybean and rapeseed oil), and combinations of these with other bio-enhancing adjuvants (ingredients that can assist or modify the action of a compound of formula (I)).

[0161] A compound of formula (I) may also be formulated for use as a seed treatment, for example as a powder composition, including a dry seed treatment powder (DS), a water-soluble powder (SS) or a water-dispersible paste treatment powder (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS). The preparations of DS, SS, WS, FS and LS compositions are very similar, respectively, to those of DP, SP, WP, SC and DC compositions. The seed treatment compositions may include an agent to aid adhesion of the composition to the seed (for example, a mineral oil or a film-forming barrier).

[0162] Wetting agents, dispersing agents and emulsifying agents may be surface-mounted SFAs of the cationic, anionic, amphoteric or non-ionic type.

[0163] Suitable cationic-type SFAs include compounds Petition 870190116135, dated 11 / 11 / 2019, page 82 / 216 73 / 200 quaternary ammonium compounds (e.g., cetyltrimethylammonium bromide), imidazolines, and amine salts.

[0164] Suitable anionic SFAs include alkali metal salts of fatty acids, aliphatic monoester salts of sulfuric acid (e.g. sodium lauryl sulfate), salts of sulfonated aromatic compounds (e.g. sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalenesulfonate and mixtures of sodium diisopropyl- and triisopropyl-naphthalenesulfonates), ether sulfates, alcohol ether sulfates (e.g. sodium laureth-3-sulfate), ether carboxylates (e.g. sodium laureth-3-carboxylate), phosphate esters (products of the reaction between one or more fatty alcohols and phosphoric acid (predominantly monoesters) or phosphorus pentoxide (predominantly diesters), for example, from the reaction between lauryl alcohol and tetraphosphoric acid; additionally, These products may be ethoxylated, sulfosuccinates, paraffin or sulfonates, taurates and olefin lignosulfonates.

[0165] Suitable amphoteric-type SFAs include betaines, propionates, and glycinates.

[0166] Suitable non-ionic SFAs include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long-chain fatty acids or hexitol anhydrides; condensation products of these partial esters with ethylene oxide; block polymers (comprising oxide of Petition 870190116135, dated 11 / 11 / 2019, p. 83 / 216 74 / 200 ethylene and propylene oxide); alkanolamides; simple esters (e.g. polyethylene glycol esters of fatty acids); amine oxides (e.g. lauryldimethylamine oxide); and lecithins.

[0167] Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and expandable clays (such as bentonite or attapulgite).

[0168] A compound of formula (I) may be applied by any of the known means of applying pesticide compounds. For example, it may be applied, in a formulated or unformulated manner, to pests or to a pest site (such as a pest habitat, or a growing plant susceptible to infestation by pests) or to any part of the plant, including foliage, stems, branches or roots, to the seed before planting or to other media where plants are growing or will be planted (such as the soil surrounding the roots, the soil in general, water-sheet or hydroponic cropping systems), directly or sprayed, dusted, applied by immersion, applied as a cream or paste formulation, applied as a vapor or applied by distribution or incorporation of a composition (such as a granular composition or a composition packaged in a water-soluble bag) into the soil or an aqueous environment.

[0169] A compound of formula (I) can also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low-volume methods, or applied by terrestrial or aerial irrigation systems. Petition 870190116135, dated 11 / 11 / 2019, page 84 / 216 75 / 200

[0170] Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use. It is frequently required that these concentrates, which may include DC, SC, EC, EW, ME, SG, SP, WP, WG, and CS, withstand storage for extended periods and, after such storage, be able to be added to water to form aqueous preparations that remain homogeneous for a period of time sufficient to allow them to be applied by conventional spraying equipment. Such aqueous preparations may contain varying amounts of a compound of formula (I) (e.g., 0.0001 to 10% by weight) depending on the purpose for which they are to be used.

[0171] A compound of formula (I) can be used in mixtures with fertilizers (e.g., fertilizers containing nitrogen, potassium, or phosphorus). Suitable formulation types include fertilizer granules. The mixtures preferably contain up to 25% by weight of the compound of formula (I).

[0172] The invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of formula (I).

[0173] The compositions of this invention may contain other compounds with biological activity, for example, micronutrients or compounds with fungicidal activity or that have plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.

[0174] The compound with formula (I) can be the only Petition 870190116135, dated 11 / 11 / 2019, page 85 / 216 76 / 200 active ingredient of the composition, or may be mixed with one or more additional active ingredients such as a pesticide, e.g., an insecticide, fungicide or herbicide, or a synergistic agent or plant growth regulator where appropriate. An additional active ingredient may provide a composition having a broader spectrum of activity or increased persistence at a locus; have a synergistic effect on the activity or complement the activity (e.g., by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components. The particular additional active ingredient will depend on the intended use of the composition.

[0175] The compounds of the invention are also useful in the field of animal health, e.g., they can be used against parasitic invertebrate pests, more preferably against parasitic invertebrate pests in or on an animal. Examples of pests include nematodes, trematodes, cestodes, flies, mites, ticks, lice, fleas, bedbugs and larvae. The animal can be a non-human animal, e.g., an animal associated with agriculture, e.g., a cow, a pig, a sheep, a goat, a horse, or a donkey, or a pet, e.g., a dog or a cat.

[0176] In a further aspect, the invention provides a compound of the invention for use in a therapeutic treatment method.

[0177] In a further aspect, the invention relates to a method of controlling parasitic invertebrate pests in or on an animal, comprising administering a Petition 870190116135, dated 11 / 11 / 2019, page 86 / 216 77 / 200 effective pesticidal quantity of a compound of the invention. Administration may be, for example, oral administration, parenteral administration, or external administration, e.g., to the surface of the animal's body. In a further aspect, the invention relates to a compound of the invention for controlling parasitic invertebrate pests on or in an animal. In a further aspect, the invention relates to the use of a compound of the invention in the manufacture of a medicament for controlling parasitic invertebrate pests on or in an animal.

[0178] In a further aspect, the invention relates to a method of controlling parasitic invertebrate pests comprising administering a pesticide-effective amount of a compound of the invention into the environment in which an animal resides.

[0179] In a further aspect, the invention relates to a method of protecting an animal from a parasitic invertebrate pest comprising administering to the animal an effective amount in pesticide terms of a compound of the invention. In a further aspect, the invention relates to a compound of the invention for use in protecting an animal from a parasitic invertebrate pest. In a further aspect, the invention relates to the use of a compound of the invention in the manufacture of a medicament for protecting an animal from a parasitic invertebrate pest.

[0180] In a further aspect, the invention provides a method of treating an animal suffering from a parasitic invertebrate pest, comprising administering to the animal a pesticide-effective amount of a compound of the invention. In a further aspect, the invention... Petition 870190116135, dated 11 / 11 / 2019, p. 87 / 216 78 / 200 refers to a compound of the invention for use in the treatment of an animal suffering from a parasitic invertebrate plague. In a further aspect, the invention relates to the use of a compound of the invention in the manufacture of a medicament for the treatment of an animal suffering from a parasitic invertebrate plague.

[0181] In a further aspect, the invention provides a pharmaceutical composition comprising a compound of the invention and a pharmaceutically suitable excipient.

[0182] The compounds of the invention can be used alone or in combination with one or more other biologically active ingredients.

[0183] In one aspect, the invention provides a combination product comprising a pesticide-effective amount of component A and a pesticide-effective amount of component B, wherein component A is a compound of the invention and component B is a compound as described below.

[0184] The compounds of the invention can be used in combination with anthelmintic agents. Such anthelmintic agents include compounds selected from the class of macrocyclic lactone compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives, as described in EP-357460, EP444964 and EP-594291. Additional anthelmintic agents include semi-synthetic and biosynthetic avermectin / milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include benzimidazoles such as Petition 870190116135, dated 11 / 11 / 2019, page 88 / 216 79 / 200 albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel, or morantel. Additional anthelmintic agents include fluquicides such as triclabendazole and clorsulone, and cestocides such as praziquantel and epsiprantel.

[0185] The compounds of the invention can be used in combination with derivatives and analogues of the paraherquamide / marcfortine class of anthelmintic agents, as well as with antiparasitic oxazolines such as those disclosed in US-5478855, US-4639771 and DE-19520936.

[0186] The compounds of the invention can be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO-9615121, and also with anthelmintically active cyclic depsipeptides such as those described in WO9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO9419334, EP-382173, and EP-503538.

[0187] The compounds of the invention can be used in combination with other ectoparasiticides, for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdison agonists, such as tebufenozide and similar drugs; neonicotinoids such as imidacloprid and similar drugs.

[0188] The compounds of the invention can be used in combination with terpene alkaloids, for example those described in International Patent Application Publications Numbers WO95 / 19363 or WO04 / 72086, Petition 870190116135, dated 11 / 11 / 2019, page 89 / 216 80 / 200 particularly the compounds disclosed therein.

[0189] Other examples of such biologically active compounds with which the compounds of the invention may be used in combination include, but are not limited to, the following:

[0190] Organophosphates: acephate, azamethiphos, azinphosetyl, azinphos-methyl, bromophos, bromo-ethyl, cadusaphos, chlorethoxiphos, chlorpyrifos, chlorphenvinphos, chlormephos, demethone, demethone-S-methyl, demethylame sulfone, dimethyl, diazinon, dichlorvos, dicrotophos, dimethoate, disulphoton, ethion, ethoprophos, etrimphos, famfur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazophos, phonophos, formothion, phosthiazate, heptenophos, isazophos, isothioate, isomixation, metaphoslation, metaphoslation metidation, methyl-parathion, mevinphos, monocrotophos, naled, ometoate, oxidemeton-methyl, paraoxon, parathion, parathion-methyl, phentoate, phosalone, phospholan, phosphocarbe, phosmet, phosphamidone, phorate, phoxime, pirimiphos, pirimiphos-methyl, prophosphos, prophos, prophos, prophos pyraclophos, pyridapenthion, quinalphos, sulprophos, temephos, terbuphos, tebupyrimphos, tetrachlorvinphos, thymetone, triazophos, trichlorfon, vamidothion.

[0191] Carbamates: alanicarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, chloretocarb, ethiofencarb, fenoxycarb, fenthiocarb, furatiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-mcumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, UC-51717.

[0192] Pyrethroids: acrinatin, allethrin, alphamethrin, Petition 870190116135, dated 11 / 11 / 2019, pp. 90 / 216 81 / 200 (E) (1 R)-cis-2,2-dimethyl-3-(2-oxothiolan-3ylidenomethyl)cyclopropanecarboxylate de 5-benzyl-3furylmethyl, bifenthrin, beta-cyfluthrin, cyfluthrin, acypermethrin, beta-cypermethrin, bioalethrin, bioalethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI85193, cycloprothrin, cyhalothrin, cytithrin, cyphenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucitrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, pralethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluophene, t-fluvalinate, tefluthrin, tralomethrin, Zeta-cypermethrin.

[0193] Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezine, diofenolan, hexithiazox, ethoxazole, chlorfenazoline; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

[0194] Other antiparasitics: acequinocil, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultape, bifenazate, binapacril, bromopropylate, BTG504, BTG-505, camfeclor, Cartape, chlorobenzylate, chlordimeform, chlorfenapyr, chromafenozide, clothianidin, Petition 870190116135, dated 11 / 11 / 2019, page 91 / 216 82 / 200 ciromazina, diaclodeno, diafentiuron, DBI-3204, dinactina, diidroximetildiidroxipirrolidina, dinobuton, dinocape, endossulfano, etiprol, etofenprox, fenazaquina, flumite, MTI-800, fenpiroximato, fluacripirim, flubenzimina, flubrocitrinato, flufenzina, flufenprox, fluproxifeno, halofenprox, hidrametilnon, IKI-220, canemita, NC-196, Neemgard, nidinorterfurano, nitenpiram, SD-35651, WL108477, piridaril, propargite, protrifenbute, pimetrozina, piridabeno, pirimidifeno, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofeno, silomadina, espinosade, tebufenpirade, tetradifon, tetranactina, tiacloprida, tiociclame, tiametoxame, tolfenpirade, triazamato, trietoxispinosina, trinactina, verbutina, vertalec, YI-5301.

[0195] Fungicides: acibenzolar, aldimorph, ampropylphos, andoprim, azaconazole, azoxystrobin, benalaxyl, benomyl, bialaphos, blasticidin-S, Bordeaux mixture, bromuconazole, bupirimate, carpropamide, Captafol, Captan, carbendazim, chlorphenazole, chloroneb, chloropicrin, chlorothalonil, clozolinate, copper oxychloride, copper salts, cyflufenamide, cymoxanil, cyproconazole, cyprodinil, cyprofuram, RH-7281, diclocimet, diclobutrazol, diclomezine, dichlorane, difenoconazole, RP-407213, dimethomorph, domoxystrobin, diniconazole, diniconazole-M, dodine, edifenfos, epoxiconazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramide, fenpiclonil, fenpropidine, fenpropimorph, fentin acetate, fluaziname, fludioxonil, flumetover, flumorph / flumorlin, fentin hydroxide, fluoxastrobin, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl Petition 870190116135, dated 11 / 11 / 2019, page 92 / 216 83 / 200 aluminum, furalaxil, furametapyr, hexaconazole, ipconazole, iprobenphos, iprodione, isoprothiolane, casugamycin, cresoxim-methyl, mancozebe, manebe, mefenoxame, mepronil, metalaxyl, metconazole, metominostrobin / phenominostrobin, metrafenone, myclobutanil, neo-asozine, nicobifen, orisastrobin, oxadixil, penconazole, pencicuron, probenazole, prochloraz, propamocarbe, propioconazole, proquinazide, protioconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxifene, spiroxamine, enxofre, tebuconazole, tetraconazole, thiabendazole, tifluzamide, thiophanate-methyl, tyrame, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin, vinclozine.

[0196] Biological agents: Bacillus thuringiensis ssp. aizawai, kurstaki, delta endotoxin of Bacillus thuringiensis, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0197] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0198] Other biological agents: enrofloxacin, febantel, penetamate, moloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, piriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole.

[0199] When used in combination with other active ingredients, the compounds of the invention are preferably used in combination with the following (where Tx designates a specific compound selected from Tables 1 to 126 or Table B), which may result in a combination Petition 870190116135, dated 11 / 11 / 2019, page 93 / 216 84 / 200 synergistic with a specific active principle): imidacloprid + Tx, enrofloxacin + Tx, praziquantel + Tx, pyrantel embonate + Tx, febantel + Tx, penetamate + Tx, moloxicam + Tx, cephalexin + Tx, kanamycin + Tx, pimobendan + Tx, clenbuterol + Tx, fipronil + Tx, ivermectin + Tx, omeprazole + Tx, tiamulin + Tx, benazepril +Tx, milbemycin + Tx, ciromazine + Tx, thiamethoxam +Tx, pyriprol + Tx, deltamethrin + Tx, cefquinome +Tx, florfenicol + Tx, buserelin + Tx, cefovecin + Tx, tulathromycin + Tx, ceftiour + Tx, selamectin +Tx, carprofen + Tx, metaflumizone + Tx, moxidectin + Tx, methoprene (including S-methoprene) + Tx, clorsulon + Tx, pyrantel + Tx, amitraz + Tx, triclabendazole + Tx, avermectin + Tx, abamectin + Tx, emamectin + Tx, eprinomectin + Tx, doramectin + Tx, selamectin + Tx, nemadectin + Tx, albendazole + Tx, cambendazole + Tx, fenbendazole + Tx, flubendazole + Tx, mebendazole + Tx, oxfendazole + Tx, oxibendazole + Tx, parbendazole + Tx, tetramisole + Tx,Levamisole + Tx, pyrantel pamoate + Tx, oxantel + Tx, morantel + Tx, triclabendazole + Tx, epsiprantel + Tx, fipronil + Tx, lufenuron + Tx, ecdysone + Tx or tebufenozide + Tx; with greater preference, enrofloxacin + Tx, praziquantel + Tx, pyrantel embonate + Tx, febantel + Tx, penetamate + Tx, moloxicam + Tx, cephalexin + Tx, kanamycin + Tx, pimobendan + Tx, clenbuterol + Tx, omeprazole + Tx, tiamulin + Tx, benazepril + Tx, piriprole + Tx, cefquinome + Tx, florfenicol + Tx, buserelin + Tx, cefovecin + Tx, tulathromycin + Tx, ceftiour + Tx, selamectin + Tx, carprofen + Tx, moxidectin + Tx, clorsulon + Tx, pyrantel, Petition 870190116135, dated 11 / 11 / 2019, pp. 94 / 216 85 / 200 + Tx, eprinomectin + Tx, doramectin + Tx, selamectin + Tx, nemadectin + Tx, albendazole + Tx, cambendazole + Tx, fenbendazole + Tx, flubendazole + Tx, mebendazole + Tx, oxfendazole + Tx, oxibendazole + Tx, parbendazole + Tx, tetramisole + Tx, levamisole + Tx, pyrantel pamoate + Tx, oxantel + Tx, morantel + Tx, triclabendazole + Tx, epsiprantel + Tx, lufenuron + Tx or ecdysone + Tx; still with more preference enrofloxacin + Tx, praziquantel + Tx, pyrantel embonate + Tx, febantel + Tx, penetamate + Tx, moloxicam + Tx, cephalexin + Tx, kanamycin + Tx, pimobendan + Tx, clenbuterol + Tx, omeprazole + Tx, tiamulin + Tx, benazepril + Tx, piriprol + Tx, cefquinoma + Tx, florfenicol + Tx, buserelin + Tx, cefovecin + Tx, tulathromycin + Tx, ceftiour + Tx, selamectin + Tx, carprofen + Tx, moxidectin + Tx, clorsulon + Tx or pyrantel + Tx.

[0200] Examples of ratios include 100:1 to 1:6000, 50:1 to 1:50, 20:1 to 1:20, even more especially 10:1 to 1:10, 5:1 to 1:5, 2:1 to 1:2, 4:1 to 2:1, 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. These mixing ratios are understood as including, on the one hand, weight ratios, and also, on the other hand, molar ratios.

[0201] Of particular note is a combination where the additional active ingredient has a different site of action than the compound of formula I. In certain cases, a combination Petition 870190116135, dated 11 / 11 / 2019, pp. 95 / 216 86 / 200 with at least one other active ingredient for controlling parasitic invertebrate pests having a similar control spectrum but a different site of action will be particularly advantageous for resistance management. Thus, a combination product of the invention may comprise an effective pesticide amount of a compound of formula I and an effective pesticide amount of at least one additional active ingredient for controlling parasitic invertebrate pests having a similar control spectrum but a different site of action.

[0202] An expert in the technique recognizes that, since in the environment and under physiological conditions the salts of chemical compounds are in equilibrium with their corresponding non-saline forms, the salts share the biological usefulness of the non-saline forms.

[0203] Thus, a wide variety of salts of compounds of the invention (and active ingredients used in combination with the active ingredients of the invention) can be useful for the control of invertebrate pests and animal parasites. Salts include acid addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. The compounds of the invention also include N-oxides. Consequently, the invention comprises combinations of compounds of the invention including their N-oxides and salts, and an additional active ingredient including its N-oxides and salts.

[0204] Compositions for use in animal health may Petition 870190116135, dated 11 / 11 / 2019, pp. 96 / 216 87 / 200 may also contain formulation aids and additives, known to those skilled in the art as formulation aids (some of which may be considered as also functioning as solid diluents, liquid diluents or surfactants). Such formulation aids and additives may control: pH (buffers), foaming during processing (antifoaming agents such as polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), microbial growth within the container (antimicrobials), product freezing (antifreeze agents), color (dye / pigment dispersions), removal by washing (film formers or binders), evaporation (evaporation retarders), and other attributes of the formulations.Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers, and waxes. Examples of formulation aids and additives include those listed in McCutcheon's Volume 2: Functional Materials, annual international and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03 / 024222.

[0205] The compounds of the invention can be applied without other adjuvants, but more frequently, the application will be of a formulation comprising one or more active ingredients with suitable carriers, diluents, and surfactants and possibly in combination with a food, depending on the contemplated end use. One method of application Petition 870190116135, dated 11 / 11 / 2019, page 97 / 216 88 / 200 involves spraying an aqueous dispersion or refined oily solution of the combination products. Compositions with spray oils, spray oil concentrations, spreading agents, adjuvants, other solvents, and synergistic agents such as piperonyl butoxide often enhance the effectiveness of the compounds. Such sprays can be applied from spray containers such as a can, bottle, or other container, by means of a pump or by releasing it from a pressurized container, e.g., a pressurized aerosol spray can. Such spray compositions can take various forms, for example, sprays, mists, foams, smokes, or fog. Such spray compositions may thus additionally comprise propellants, foaming agents, etc., as the case may be.Of note is a spray composition comprising an effective pesticidal amount of a compound of the invention and a carrier. One embodiment of such a spray composition comprises an effective pesticidal amount of a compound of the invention and a propellant. Representative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures thereof. Of note is a spray composition (and a method using such a spray composition dispensed from a spray container) used to control at least one parasitic invertebrate pest selected from the group consisting of mosquitoes, blackflies, stable flies, etc. Petition 870190116135, dated 11 / 11 / 2019, pp. 98 / 216 89 / 200 deer flies, horseflies, wasps, yellow jackets, hornets, ticks, spiders, ants, gnats, and similar insects, including individually or in combinations.

[0206] Animal parasite control includes the control of external parasites that are parasitic on the surface of the host animal's body (e.g., forequarters, armpits, abdomen, inner thighs) and internal parasites that are parasitic inside the host animal's body (e.g., stomach, intestines, lungs, veins, under the skin, lymphatic tissue). External parasitic or disease-transmitting pests include, for example, larvae, ticks, lice, mosquitoes, flies, mites, and fleas. Internal parasites include heartworms, hookworms, and helminths. The compounds of the invention may be particularly suitable for controlling external parasitic pests. The compounds of the invention may be suitable for the systemic and / or non-systemic control of parasite infestation or infection in animals.

[0207] The compounds of the invention may be suitable for combating parasitic invertebrate pests that infest animal subjects, including those in wild animals, livestock and agricultural working animals. Livestock is the term used to refer (singularly or plurally) to a domesticated animal, intentionally raised in an agricultural setting to produce products such as food or fiber, or for its labor; examples of livestock include cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks and geese (e.g., raised for the use of meat, milk, butter, eggs, fur, Petition 870190116135, dated 11 / 11 / 2019, pp. 99 / 216 90 / 200 leather, feathers and / or wool). By combating parasites, fatalities and reduced performance (in terms of meat, milk, wool, hides, eggs, etc.) are reduced, such that the application of the compounds of the invention allows for more economical and simpler animal farming.

[0208] The compounds of the invention may be suitable for combating parasitic invertebrate pests that infest companion animals and pets (e.g., dogs, cats, pet birds and aquarium fish), research and experimental animals (e.g., hamsters, guinea pigs, rats and mice), as well as animals raised for / in zoos, wildlife habitats and / or circuses.

[0209] In one embodiment of this invention, the animal is preferably a vertebrate, and more preferably a mammal, bird or fish. In a particular embodiment, the animal subject is a mammal (including great apes, such as humans). Other mammalian subjects include primates (e.g., monkeys), bovines (e.g., cattle or dairy cows), porcines (e.g., swine or pigs), ovines (e.g., goats or sheep), equines (e.g., horses), canines (e.g., dogs), felines (e.g., domestic cats), camels, deer, donkeys, buffalo, antelopes, rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils, and hamsters). Birds include Anatidae (swans, ducks, and geese), Columbidae (e.g., turtle doves and pigeons), Phasianidae (e.g., partridges, grouse, and turkeys), Thesienidae (e.g., domestic chickens), Psittacines (e.g., parakeets, macaws, and parrots), game birds, and flightless birds (e.g., ostriches).

[0210] The birds treated or protected by Petition 870190116135, dated 11 / 11 / 2019, pp. 100 / 216 91 / 200 compounds of the invention may be associated with commercial or non-commercial poultry farming. These include Anatidae, such as swans, geese, and ducks; Columbidae, such as turtle doves and domestic pigeons; Phasianidae, such as partridges, grouse, and turkeys; Thesienidae, such as domestic chickens; and Psittacines, such as parakeets, macaws, and parrots raised for the pet or collector market, among others.

[0211] For the purposes of the present invention, the term fish is understood to include, without limitation, the grouping of Teleosti fish, i.e., teleosts. Both the order Salmoniformes (which includes the family Salmonidae) and the order Perciformes (which includes the family Centrarchidae) are contained within the Teleosti grouping. Examples of potential recipient fish include Salmonidae, Serranidae, Sparidae, Cichlidae, and Centrarchidae, among others.

[0212] Other animals are also contemplated as benefiting from the inventive methods, including marsupials (such as kangaroos), reptiles (such as farmed turtles), and other economically important domestic animals, for which the inventive methods are safe and effective in treating or preventing parasitic infection or infestation.

[0213] Examples of parasitic invertebrate pests controlled by administering a pesticide-effective amount of the compounds of the invention to an animal to be protected include ectoparasites (arthropods, mites, etc.) and endoparasites (helminths, e.g., nematodes, trematodes, cestodes, acanthocephalans, etc.). Petition 870190116135, dated 11 / 11 / 2019, pp. 101 / 216 92 / 200

[0214] The disease or group of diseases generically described as helminthiasis is due to infection of an animal host with parasitic worms known as helminths. The term helminths is intended to include nematodes, trematodes, cestodes, and acanthocephalans. Helminthiasis is a prevalent and serious economic problem in domesticated animals such as pigs, sheep, horses, cattle, goats, dogs, cats, and poultry.

[0215] Among helminths, the group of worms described as nematodes causes widespread and sometimes severe infection in various animal species.

[0216] Nematodes contemplated for treatment by the compounds of the invention include, without limitation, the following genera: Acanthocheilonema, Aelurostrongylus, Ancylostoma, Angiostrongylus, Ascaridia, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Crenosoma, Dictyocaulus, Dioctophyme, Dipetalonema, Diphyllobothrium, Dirofilaria, Dracunculus, Enterobius, Filaroides, Haemonchus, Heterakis, Lagochilascaris, Loa, Mansonella, Muellerius, Necator, Nematodirus, Oesophagostomum, Ostertagia, Oxyuris, Parafilaria, Parascaris, Physaloptera, Protostrongylus, Setaria, Spirocerca, Stephanofilaria, Strongyloides, Strongylus, Thelazia, Toxascaris, Toxocara, Trichinella, Trichonema, Trichostrongylus, Trichuris, Uncinaria and Wuchereria.

[0217] Of the nematode genera listed above, the most common ones that infect the animals mentioned above are Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Petition 870190116135, dated 11 / 11 / 2019, pp. 102 / 216 93 / 200 Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, and Parascaris. Some of these, such as Nematodirus, Cooperia, and Oesophagostomum, primarily attack the intestinal tract, while others, such as Haemonchus and Ostertagia, are more prevalent in the stomach, while others, such as Dictyocaulus, are found in the lungs. Still other parasites may be located in other tissues such as the heart and blood vessels, subcutaneous and lymphatic tissue, and similar tissues.

[0218] Trematodes contemplated for treatment by the invention and inventive methods include, without limitation, the following genera: Alaria, Fasciola, Nanophyetus, Opisthorchis, Paragonimus and Schistosoma.

[0219] Cestodes contemplated for treatment by the invention and inventive methods include, without limitation, the following genera: Diphyllobothrium, Diplydium, Spirometra and Taenia.

[0220] The most common genera of parasites in the human gastrointestinal tract are

[0221] Ancylostoma, Necator, Ascaris, Strongy hids, Trichinella, Capillaria, Trichuris and Enterobius. Other genera of medically important parasites that are found in the blood or other tissues and organs outside the gastrointestinal tract are filarial worms such as Wuchereria, Brugia, Onchocerca and Loa, as well as Dracunculus and extraintestinal stages of the intestinal worms Strongyloides and Trichinella.

[0222] Numerous other genera and species of helminths are known to the art, and are also contemplated for Petition 870190116135, dated 11 / 11 / 2019, pp. 103 / 216 94 / 200 to be treated by the compounds of the invention. These are listed in great detail in Textbook of Veterinary Clinical Parasitology, Volume 1, Helminths, EJL Soulsby, FA Davis Co., Philadelphia, Pa.; Helminths, Arthropods and Protozoa (6th Edition of Monnig's Veterinary Helminthology and Entomology), EJL Soulsby, Williams and Wilkins Co., Baltimore, Md.

[0223] The compounds of the invention may be effective against a number of animal ectoparasites (e.g., arthropod ectoparasites of mammals and birds).

[0224] Insect and mite pests include, for example, biting insects such as flies and mosquitoes, mites, ticks, lice, fleas, bedbugs, parasitic worms, and the like.

[0225] Adult flies include, for example, the horn fly or Haematobia irritans, the horse fly or Tabanus spp., the stable fly or Stomoxys calcitrans, the black fly or Simulium spp., the deer fly or Chrysops spp., the sheep fly or Melophagus ovinus, and the tsetse fly or Glossina spp. Parasitic worms include, for example, the horse fly (Oestrus ovis and Cuterebra spp.), the blowfly or Phaenicia spp., the screwworm or Cochliomyia hominivorax, the cattle grub or Hypoderma spp., the woolly grub, and the equine Gastrophilus. Mosquitoes include, for example, Culex spp., Anopheles spp., and Aedes spp.

[0226] Mites include Mesostigmalphatalpha spp., e.g., mesostigmatids such as the chicken mite, Dermalphanyssus galphallinalphae; scabies mites such as Sarcoptidae spp., for example, Petition 870190116135, dated 11 / 11 / 2019, pp. 104 / 216 95 / 200 Salpharcoptes scalphabiei; scabies mites such as Psoroptidae spp., including Chorioptes bovis and Psoroptes ovis; larvae, e.g., Trombiculidae spp., e.g. the North American larva, Trombiculalpha alphalfreddugesi.

[0227] Ticks include, for example, soft-bodied ticks including Argasidae spp., for example Argalphas spp. and Ornithodoros spp.; hard-bodied ticks including Ixodidae spp., for example Rhipicephalphalus sanguineus, Dermacentor variabilis, Dermacentor andersoni, Amblyomma americanum, Ixodes scapularis and other Rhipicephalus spp. (including the former genus Boophilus).

[0228] Lice include, for example, sucking lice, e.g., Menopon spp. and Bovicola spp.; biting lice, e.g., Haematopinus spp., Linognathus spp., and Solenopotes spp.

[0229] Fleas include, for example, Ctenocephalides spp., such as dog flea (Ctenocephalides canis) and cat flea (Ctenocephalides felis); Xenopsylla spp., such as oriental rat flea (Xenopsylla cheopis); and Pulex spp., such as human flea (Pulex irritans).

[0230] Bed bugs include, for example, Cimicidae or, for example, the common bed bug (Cimex lectularius); Triatominae spp., including triatomine bugs also known as kissing bugs; for example Rhodnius prolixus and Triatoma spp.

[0231] Generally, flies, fleas, lice, mosquitoes, gnats, mites, ticks, and helminths cause tremendous losses in the livestock and pet sectors. Arthropod parasites are also a nuisance to humans and can be vectors of disease-causing organisms in humans and animals. Petition 870190116135, dated 11 / 11 / 2019, pages 105 / 216 96 / 200

[0232] Numerous different parasitic invertebrate pests are known in the art, and are also contemplated for treatment by the compounds of the invention. These are listed in great detail in Medical and Veterinary Entomology, DS Kettle, John Wiley and Sons, New York and Toronto; Livestock Arthropod Pest Control: A Technology Review, RO Drummand, JE George, and SE Kunz, CRC Press, Boca Raton, F1A.

[0233] The compounds of the invention may also be effective against ectoparasites including: flies such as Haematobia (Lyperosia) irritans (horn fly), Simulium spp., (black fly), Glossina spp., (tsetse flies), Hydrotaea irritans (head fly), Musca autumnalis (face fly), Musca domestica (house fly), Morellia simplex (sweat fly), Tabanus spp., (horse fly), Hypoderma bovis, Hypoderma lineatum, Lucilia sericata, Lucilia cuprina (green blowfly), Calliphora spp., (blowfly), Protophormia spp., Oestrus ovis (nasal botfly), Culicoides spp., (mosquitoes), Hippobosca equine, Gastrophilus intestinalis, Gastrophilus haemorrhoidalis and Gastrophilus nasalis; Lice such as Bovicola (Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicola subrostratus, Heterodoxus spiniger, Lignonathus setosus and Trichodectes canis; lice flies such as Melophagus ovinus; and mites such as Psoroptes spp., Sarcoptes scabiei, Chorioptes bovis, Demodex equi, Cheyletiella spp., Notoedres cati, Trombicula spp., and Otodectes cyanotis (ear mites).

[0234] The treatments of the invention are carried out by conventional means such as by enteral administration in Petition 870190116135, dated 11 / 11 / 2019, pages 106 / 216 97 / 200 form, for example, of tablets, capsules, drinks, potions, granules, pastes, pills, nutritional procedures, or suppositories; or by parenteral administration, such as, for example, by injection (including intramuscular, subcutaneous, intravenous, intraperitoneal) or implants; or by nasal administration.

[0235] When the compounds of the invention are applied in combination with an additional biologically active ingredient, they can be administered separately, e.g., as separate compositions. In this case, the biologically active ingredients can be administered simultaneously or sequentially. Alternatively, the biologically active ingredients can be components of a composition.

[0236] The compounds of the invention can be administered in a controlled-release form, for example in slow-release formulations administered subcutaneously or orally.

[0237] Typically, a parasiticidal composition according to the present invention comprises a compound of the invention, optionally in combination with an additional biologically active ingredient, or its N-oxides or salts, with one or more pharmaceutically or veterinary acceptable carriers comprising excipients and auxiliaries selected with respect to the intended route of administration (e.g., oral or parenteral administration such as injection) and in accordance with common practice. Additionally, a suitable carrier is selected based on compatibility with one or more active ingredients in the composition, including considerations such as stability. Petition 870190116135, dated 11 / 11 / 2019, pp. 107 / 216 98 / 200 with respect to pH and moisture content. Therefore, noteworthy compounds of the invention for protecting an animal from an invertebrate parasitic pest comprise an effective amount in parasiticidal terms of a compound of the invention, optionally in combination with an additional biologically active ingredient and at least one carrier.

[0238] For parenteral administration including intravenous, intramuscular and subcutaneous injection, the compounds of the invention may be formulated as a suspension, solution or emulsion in oily or aqueous vehicles, and may contain adjuncts such as suspending, stabilizing and / or dispersing agents.

[0239] The compounds of the invention can also be formulated for bolus injection or continuous infusion. Pharmaceutical compositions for injection include aqueous solutions of water-soluble forms of active ingredients (e.g., a salt of an active compound), preferably in physiologically compatible buffers containing other excipients or auxiliaries as are known in the pharmaceutical formulation art. Additionally, suspensions of the active compounds can be prepared in a lipophilic vehicle. Suitable lipophilic vehicles include fatty oils such as sesame oil, esters of synthetic fatty acids such as ethyl oleate and triglycerides, or materials such as liposomes.

[0240] Aqueous suspensions for injection may contain substances that increase the viscosity of the suspension, such as sodium carboxymethylcellulose, sorbitol, or dextran. Injection formulations may be presented in unit dosage form, e.g., in ampoules or containers. Petition 870190116135, dated 11 / 11 / 2019, pp. 108 / 216 99 / 200 multidose. Alternatively, the active ingredient may be in powder form for mixing with a suitable vehicle, e.g., sterile, pyrogen-free water, prior to use.

[0241] In addition to the formulations described above, the compounds of the invention may also be formulated as a depot preparation. Such long-acting formulations may be administered by implantation (e.g. subcutaneously or intramuscularly) or by intramuscular or subcutaneous injection.

[0242] The compounds of the invention can be formulated for this route of administration with suitable polymeric or hydrophobic materials (for example, in an emulsion with a pharmacologically acceptable oil), with ion-exchange resins, or as a sparingly soluble derivative such as, without limitation, a sparingly soluble salt.

[0243] For administration by inhalation, the compounds of the invention can be administered in the form of an aerosol spray using a pressurized container or a nebulizer and a suitable propellant, e.g., without limitation, dichlorodifluoromethane, trichlorofluoromethane, dichlorotetrafluoroethane or carbon dioxide. In the case of a pressurized aerosol, the dosing unit can be controlled by a valve to dispense a calibrated quantity.

[0244] Capsules and cartridges, for example of gelatin, may be formulated for use in an inhaler or insufflator containing a powder mixture of the compound and a suitable powder base such as lactose or starch.

[0245] The compounds of the invention may have favorable pharmacokinetic and pharmacodynamic properties, Petition 870190116135, dated 11 / 11 / 2019, pp. 109 / 216 100 / 200 providing systemic availability from oral administration and ingestion. Therefore, after ingestion by the animal to be protected, effective parasiticidal concentrations of a compound of the invention in the bloodstream can protect the treated animal from blood-sucking pests such as fleas, ticks and lice. Therefore, noteworthy is a composition for protecting an animal from an invertebrate parasitic pest in a form for oral administration (i.e., comprising, in addition to an effective parasiticidal amount of a compound of the invention, one or more selected carriers of binders and fillers suitable for oral administration and carriers of feed concentrates).

[0246] For oral administration in the form of solutions (the form most rapidly available for absorption), emulsions, suspensions, pastes, gels, capsules, tablets, boli, powders, granules, rumen retention blocks and feed / water / lick blocks, the compounds of the invention can be formulated with binders / fillers known in the art to be suitable for compositions for oral administration, such as sugars and sugar derivatives (e.g., lactose, sucrose, mannitol, sorbitol), starch (e.g., corn starch, wheat starch, rice starch, potato starch), cellulose and derivatives (e.g., methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), protein derivatives (e.g., zein, gelatin), and synthetic polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone). If desired, lubricants (e.g., magnesium stearate) and disintegrating agents (e.g., polyvinylpyrrolidone) may be added. Petition 870190116135, dated 11 / 11 / 2019, pages 110 / 216 101 / 200 crosslinked, agar, alginic acid) and dyes or pigments. Pastes and gels also frequently contain adhesives (e.g., acacia, alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) to help maintain the composition in contact with the oral cavity and prevent them from being easily ejected.

[0247] In one embodiment, a composition of the present invention is formulated in a chewable and / or edible product (e.g., a chewable treat or edible tablet). Such a product will ideally have a taste, texture and / or aroma that is agreeable to the animal to be protected, in order to facilitate oral administration of the compounds of the invention.

[0248] If the parasiticidal compositions are in the form of feed concentrates, the carrier is typically selected from high-performance feed, feed cereals or protein concentrates.

[0249] Such compositions containing feed concentrates may, in addition to the active parasiticidal ingredients, comprise additives that promote animal health or growth, improve meat quality in animals destined for slaughter, or are otherwise useful for animal husbandry.

[0250] These additives may include, for example, vitamins, antibiotics, chemotherapeutic agents, bacteriostatic agents, fungistatic agents, coccidiostatic agents and hormones.

[0251] The compound of the invention can also be formulated in rectal compositions such as suppositories or retention enemas, using, for example, conventional bases for Petition 870190116135, dated 11 / 11 / 2019, pages 111 / 216 102 / 200 suppositories such as cocoa butter or other glycerides.

[0252] The formulations for the method of this invention may include an antioxidant, such as BHT (butylated hydroxytoluene). The antioxidant is generally present in amounts of 0.1-5 percent (w / vol). Some formulations require a solubilizer, such as oleic acid, to dissolve the active agent, particularly if spinosad is included. Common spreading agents used in these pouring formulations include isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of saturated C12-C18 fatty alcohols, oleic acid, oleyl ester, ethyl oleate, triglycerides, silicone oils, and dipropylene glycol methyl ether. The pouring formulations for the method of this invention are prepared according to known techniques. When the spill formulation is a solution, the parasiticide / insecticide is mixed with the carrier or vehicle, using heat and agitation if required.Auxiliary or supplementary ingredients may be added to the active agent and vehicle mixture, or they may be mixed with the active agent before the vehicle is added. Pour formulations in the form of emulsions or suspensions are similarly prepared using known techniques.

[0253] Other delivery systems may be employed for relatively hydrophobic pharmaceutical compounds. Liposomes and emulsions are well-known examples of delivery vehicles or carriers for hydrophobic drugs. Additionally, they may be Petition 870190116135, dated 11 / 11 / 2019, pp. 112 / 216 103 / 200 organic solvents such as dimethyl sulfoxide are used if necessary.

[0254] The application rate required for effective control of parasitic invertebrate pests (e.g., effective amount of pesticide) will depend on factors such as the species of parasitic invertebrate pest to be controlled, the pest's life cycle, life stage, size, location, time of year, crop or animal host, feeding behavior, mating behavior, ambient humidity, temperature, and the like. An expert in the art can easily determine the effective amount of pesticide required for the desired level of control of parasitic invertebrate pests.

[0255] In general, for veterinary use, the compounds of the invention are administered in an amount effective in pesticidal terms to an animal, particularly a homeothermic animal, to be protected from parasitic invertebrate pests.

[0256] An effective amount of pesticide is the amount of active ingredient required to achieve an observable effect of decreasing the occurrence or activity of the target parasitic invertebrate pest. A person skilled in the art will appreciate that the effective dose in pesticide terms may vary for the various compounds and compositions useful for the method of the present invention, the desired pesticidal effect and duration, the target species of parasitic invertebrate pest, the animal to be protected, the method of application and the like, and the amount required to achieve a particular result can be determined by Petition 870190116135, dated 11 / 11 / 2019, pages 113 / 216 104 / 200 simple experimentation.

[0257] For oral or parenteral administration to animals, a dose of the compositions of the present invention administered at appropriate intervals typically ranges from about 0.01 mg / kg to about 100 mg / kg, and preferably from about 0.01 mg / kg to about 30 mg / kg of the animal's body weight.

[0258] Suitable intervals for administering the compositions of the present invention to animals range from about daily to about annually. Administration intervals of note range from about weekly to about once every 6 months. Of particular note are monthly administration intervals (i.e., administering the compounds to the animal once a month).

[0259] The present invention also provides a process 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 pest control comprises applying the compositions of the invention to the target pests, their locus, or a surface or substrate by brushing, rolling, spraying, spreading, or immersion. As an example, an application by IRS (internal residual spraying) to a surface such as a wall, ceiling, or floor surface is contemplated by the method of the invention. In another embodiment, the application of such compositions to a substrate such as a nonwoven or woven material in the form of (or which can be used in the manufacture of) knitwear, clothing, bedding, curtains, and tents is contemplated.

[0260] In one embodiment, the method for controlling such Petition 870190116135, dated 11 / 11 / 2019, pp. 114 / 216 105 / 200 pests comprises applying an effective amount of the compositions according to the invention to the target pests, their locus, or a surface or substrate, so as to provide effective residual pesticidal activity on the surface or substrate. Such application may be done by brushing, displacement, spraying, spreading or immersion of the pesticidal composition of the present invention. As an example, an IRS application to a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention, so as to provide effective residual pesticidal activity on the surface. In another embodiment, the application of such compositions for residual pest control to a substrate such as a woven material in the form of (or that can be used in the manufacture of) knitwear, clothing, bedding, curtains and tents is contemplated.

[0261] The substrates including nonwovens, wovens or knitted fabrics to be treated may be made of natural fibers such as cotton, raffia, jute, linen, sisal, plain warp, or wool, or synthetic fibers such as polyamide, polyester, polypropylene, polyacrylonitrile or similar. Polyesters are particularly suitable. Methods of textile treatment are known, e.g., from Handbuch Textilveredlung: Band 1: Ausrüstung, Band 2: Farbgebung, Band 3: Beschichtung, Band 4: Umwelttechnik; Verlag: Deutscher Fachverlag; Auflage: 15., überarbeitete Ausgabe (17 April 2006); ISBN-10: 3866410123; ISBN-13: 9783866410121, see especially Volume 1: Assembly pages 27-198, more preferably on page 118; or WO2008151984 or WO2003034823 or US5631072 or WO200564072 or Petition 870190116135, dated 11 / 11 / 2019, pages 115 / 216 106 / 200 WO2006128870 or EP1724392 or WO2005064072 or WO2005113886 or WO2007090739.

[0262] The term plant, as used here, includes seedlings, shrubs and trees.

[0263] The term crops or plants is to be understood as also including culture plants that have been so transformed by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as those known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

[0264] The toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as 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; or insecticidal proteins from nematode-colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or white bellflower lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin inhibitors, cystatin, papain; proteins. Petition 870190116135, dated 11 / 11 / 2019, pages 116 / 216 107 / 200 ribosome inactivating agents (RIPs), such as ricin, maize RIP, abrin, lufin, saporin or briodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyltransferase, cholesterol oxidases, ecdysone inhibitors, HMG-CoA reductase, ion channel blockers, such as sodium or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

[0265] In the context of the present invention, δ-endotoxins are to be understood to mean, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A, also expressly hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are recombinantly produced by a novel combination of different domains of these proteins (see, for example, WO 02 / 15701). Truncated toxins are known, for example a truncated Cry1Ab. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are substituted. In such amino acid substitutions, protease recognition sequences not naturally present are preferentially inserted into the toxin, as for example in the case of Cry3A055, a cathepsin G recognition sequence is inserted into a Cry3A toxin (see WO 03 / 018810).

[0266] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-APetition 870190116135, dated 11 / 11 / 2019, p. 117 / 216 108 / 200 427 529, EP-A-451 878 and WO 03 / 052073.

[0267] The processes for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90 / 13651.

[0268] The toxin contained in transgenic plants gives the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).

[0269] Transgenic plants containing one or more genes that encode insecticide resistance and express one or more toxins are known, and some of them are commercially available. Examples of such plants are: YieldGard® (a variety of maize that expresses a Cry1Ab toxin); YieldGard Rootworm® (a variety of maize that expresses a Cry3Bb1 toxin); YieldGard Plus® (a variety of maize that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink® (a variety of maize that expresses a Cry9C toxin); Herculex I® (a variety of maize that expresses a Cry1Fa2 toxin and the enzyme phosphinothricin-N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a variety of cotton that expresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses a Cry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac and a Cry2Ab toxin); VipCot® (cotton variety that Petition 870190116135, dated 11 / 11 / 2019, pages 118 / 216 109 / 200 expresses Vip3A and Cry1Ab toxin); NewLeaf® (potato variety that expresses Cry3A toxin); NatureGard®, Agrisure® GT Advantage (glyphosate-tolerant trait GA21), Agrisure® CB Advantage (corn borer (CB) trait Bt11) and Protecta®.

[0270] Additional examples of such transgenic crops are: 1. Bt11 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays that has been made resistant to attack by the European maize borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium. 2. Bt176 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays that has been made resistant to attack by the European maize borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a Cry1Ab toxin. Bt176 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium. 3. Maize MIR604 from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize that has been made insect-resistant through the transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by the insertion of a cathepsin G protease recognition sequence. The preparation of such maize plants Petition 870190116135, dated 11 / 11 / 2019, pages 119 / 216 110 / 200 transgenic is described in WO 03 / 018810. 4. MON 863 from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects. 5. IPC 531 Cotton from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02. 6. Maís 1507 from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Maís genetically modified to express the Cry1F protein in order to achieve resistance to certain Lepidoptera insects, and the PAT protein in order to achieve tolerance to the herbicide glufosinate ammonium. 7. Maís NK603 x MON 810 from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. It consists of conventionally improved hybrid maize varieties obtained by crossing the genetically modified varieties NK603 and MON 810. The NK603 χ MON 810 maize transgenically expresses the CP4 EPSPS protein, obtained from the CP4 strain of Agrobacterium spp., which provides tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki which provides tolerance to certain Lepidoptera, including the European corn borer.

[0271] The activity of the compositions according to the invention can be considerably extended, and adapted to prevailing circumstances, by the addition of other active ingredients in terms of insecticides, acaricides and / or Petition 870190116135, dated 11 / 11 / 2019, pp. 120 / 216 111 / 200 fungicides. Mixtures of compounds of formula I with other active ingredients from an insecticidal, acaricidal and / or fungicidal point of view may also have surprising additional advantages, which can also be described, in a broader sense, as synergistic activity. For example, better plant tolerance, reduced phytotoxicity, insects can be controlled at different stages of development, or better behavior during production, for example during grinding or mixing, during storage or during use.

[0272] The suitable additions to active ingredients here are, for example, representative of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

[0273] The following mixtures of compounds of formula I with active ingredients are preferred (the abbreviation TX means “a specific compound selected from Table 1 to 126 or Table B of the present invention”): an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX, an acaricide selected from the group of substances consisting of 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate Petition 870190116135, dated 11 / 11 / 2019, pp. 121 / 216 112 / 200 (IUPAC / Chemical Abstracts name) (1059) + TX, 2-fluoro-Nmethyl-N -1-naphthylacetamide (IUPAC name) (1295) + TX, 4chlorophenylphenylsulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocil (3) + TX, acetoprol [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidithin (870) + TX, amidoflumet [CCN] + TX, amidothioate (872) + TX, amiton (875) + TX, hydrogen oxalate amiton (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenious oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (IUPAC name) (888) + TX, azocyclotine (46) + TX, azotoate (889) + TX, benomyl (62) + TX, benoxaphos (alternative name) [CCN] + TX, benzoximate (71) + TX, benzyl benzoate (IUPAC name) [CCN] + TX, bifenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name) + TX, bromocyclene (918) + TX,bromophos (920) + TX, bromophos-ethyl (921) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butocarboxim (103) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, calcium polysulfide (IUPAC name) (111) + TX, camfeclor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophenothione (947) + TX, CGA 50'439 (development code) (125) + TX, quinomethionate (126) + TX, chlorbenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorfenetol (968) + TX, chlorfenson (970) + TX, chlorfen sulfide (971) + TX, chlorfenvinphos (131) + TX, chlorobenzilate (975) + TX, chlormebuform (977) + TX, Petition 870190116135, dated 11 / 11 / 2019, pp. 122 / 216 113 / 200 chloromethioron (978) + TX, chloropropylate (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, cinerin I (696) + TX, cinerin II (696) (696) + TX, clofentezine (158) + TX, closantel (alternate name) [CCN] + TX, coumaphos (174) + TX, crotamitone (alternate name) [CCN] + TX, crotoxifos (1010) + TX, cufranebe (1013) + TX, ciantho (1020) + TX ciflumethofen (CAS Reg. No.: 400882-07-7) + TX, cihalothrin (196) + TX, cihexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX, demefion (13,37) + TX-O (1037) + TX, demephion-S (1037) + TX, demetone (1038) + TX, demetone-methyl (224) + TX, demetone-O (1038) + TX, demetone-O-methyl (224) + TX, demethone-S (1038) + TX, demetone-S (224) + TX-demethyl (224) demetone-S-methylsulfone (1039) + TX, diaphentiuron (226) + TX, dialiphos (1042) + TX, diazinon (227) + TX, diclofluanide (230) + TX, dichlorvos (236) + TX, diclyphos (alternative name) + TX, dico (22) + TXdicrotophos (243) + TX, dienochlor (1071) + TX, dimefox (1081) + TX, dimethoate (262) + TX, dinactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinobuton (269) + TX, dinocape (270) + TX, dinocape-4 [CCN] + TX, dinocape-6 [CCN] + TX, dinocton (1090) + TX, dinopenton (1092) + TX, dinosulfone (1097) + TX, dinoterbon (1098) + TX, dioxathione (1102) + TX, diphenylsulfone (IUPAC name) (1103) + TX, disulfiram (alternative name) [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dofenapin (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothion (1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethion (309) + TX, ethoate-methyl (1134) + TX, ethoxazole, Petition 870190116135, dated 11 / 11 / 2019, pages 123 / 216 114 / 200 (320) + TX, etrinphos (1142) + TX, phenazaflor (1147) + TX, phenazaquine (328) + TX, phenbutatine oxide (330) + TX, phenothiocarbe (337) + TX, phenpropatrine (TX34) + alternative phenotype + TX, fenpiroximate (345) + TX, fensone (1157) + TX, fentriphanil (1161) +TX, fenvalerato (349) + TX, fipronil (354) + TX, fluacripirim (360) + TX, fluazurone (1166) + TX, flubenzimine (117) + TX (366) + TX, flucitrinate (367)+ TX, fluenethyl (1169) + TX, flufenoxurone (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (developmental clotting) (115) TX, formatanate (405) + TX, formatanate hydrochloride (405) + TX, formotion (1192) + TX, formparanate (1193) + TX, gammaHCH (430) + TX, gliodine (1205) + TX, halfenprox (424) + TX, heptanate (405) + TX, + TX hexadecyl cyclopropanocarboxylate (IUPAC name / Chemical Abstracts) (1216) + TX, hexithiazox (441) + TX, iodomethane (IUPAC name) (542) + TX,isocarbophos (alternative name) (473) + TX, Isopropyl (methoxyaminothiophosphoryl)salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, iodofenphos (1248) + TX, lindane (430) + TX, lufenuron (490) + TX, malathion (492) + TX, malonobene (1254) + TX, mecarban (502) + TX, mephospholan (1261) + TX, mesulfene (alternative name) [CCN] + TX, methacryphos (1266) + TX, methamidophos (527) + TX, methidathion (529) + TX, methiocarb (530) + TX, methomyl (531) + TX, methyl bromide (537) +, TX, metolcarb (550) + TX, mevinfos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, Petition 870190116135, dated 11 / 11 / 2019, pages 124 / 216 115 / 200 monocrotophos (561) + TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naled (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, nifluride (1309) + TX, nicomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb 1:1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxideprophos (1324) + TX, oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, fencapton (1330) + TX, fentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholan (1338) + TX, phosmet (638) + TX, phosfamidon (639) + TX, foxim (642) + TX, pirimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacil (1354) + TX, propargita (671) + TX,propetanphos (673) + TX, propoxur (678) + TX, protidation (1360) + TX, protoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridabene (699) + TX, pyridafenthion (701) + TX, pyrimidifene (706) + TX, pyrimitate (1370) + TX, quinalfos (711) + TX, quinthiophos (1381) + TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, scradane (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, sofamide (1402) + TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternative name), Petition 870190116135, dated 11 / 11 / 2019, pages 125 / 216 116 / 200 [CCN] + TX, sulfluramide (750) + TX, sulfotepe (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, tau-fluvalinate (398) + TX, tebufenpyrad (763) + TX, TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorvinphos (777) + TX, tetradifon (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, thiafenox (alternative name) + TX, thiocarboxymine (1431) + TX, thiofanox (800) + TX, thiometon (801) + TX, thioquinox (1436) + TX, thuringiensin (alternative name) [CCN] + TX, triamiphos (1441) + TX, triaratene (1443) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trifenophos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothion (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX, an algaecide selected from the group of substances consisting of betoxazine [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, cibutrin [CCN] + TX, diclone (1052) + TX,dichlorophene (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name), Petition 870190116135, dated 11 / 11 / 2019, pages 126 / 216 117 / 200 [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX, an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, dioctanoate copper (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophene (232) + TX, dipyrithione (1105) + TX, dodicine (1112) + TX, phenaminosulfe (1144) + TX, formaldehyde (404) + TX, hydrargaphene (alternative name) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrin (580) + TX,octilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, hydroxyquinoline-potassium sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, teclophthalam (766) + TX, and thiomersal (alternative name), [CCN] + TX, a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus Petition 870190116135, dated 11 / 11 / 2019, pp. 127 / 216 118 / 200 (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea (alternative name) (151) + TX, Cryptolaemus montrouzieri (alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433) + TX, Hippodamia convergens (alternative name) (442) + TX, Leptomastix dactylopii (alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, Metaphycus helvolus (alternative name) (522) + TX, Metarhizium anisopliae var. Petition 870190116135, 11 / 11 / 2019, pág. 128 / 216119 / 200 acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575) + TX, Orius spp. (alternative name) (596) + TX, Paecilomyces fumosoroseus (alternative name) (613) + TX, Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua multicapsid nuclear poliedrose virus (scientific name) (741) + TX, Steinernema bibionis (alternative name) (742) + TX, Steinernema carpocapsae (alternative name) (742) + TX, Steinernema feltiae (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp.(alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX, a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX, a chemosterifying agent selected from the group of substances consisting of afolate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatife (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa. [CCN] + TX, metepa [CCN] + TX, metiotepa [CCN] + TX, methyl afolate [CCN] + TX, morzide [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa Petition 870190116135, dated 11 / 11 / 2019, pp. 129 / 216 120 / 200 (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX, an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222) + TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E,Z)tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) IUPAC) (285) + TX, (Z)hexadec-11-enal (IUPAC name) (436) + TX, (Z)hexadec-11-en-1-yl acetate (IUPAC name) (437) + TX, (Z)-hexadec-13-en-11-en-1-yl acetate (IUPAC name) (438) + TX, (Z)icos-13-en-10-one (IUPAC name) (448) + TX, (Z)-tetradec-7en-1-al (IUPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783) + TX, (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784) + TX, acetate (7E,9Z)-dodeca-7,9dien-1-yl (IUPAC name) (283) + TX, (9Z, acetate)11E)tetradeca-9,11-dien-1-yl (IUPAC name) (780) + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781) + TX, 14-methyloctadec-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name) (544) + TX, alpha-multistriatin (alternative name) [CCN] + TX, brevicomine (alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemone (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, acetate dodec-8-en-1-yl (IUPAC name) (286) + TX, dodec-9-en-1-yl acetate (IUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, 4, Petition 870190116135, dated 11 / 11 / 2019, pp. 130 / 216 121 / 200 ethyl methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN] + TX, gossylure (alternative name) (420) + TX, grandlure (421) + TX, grandlure I (alternative name) (421) + TX, grandlure II (alternative name) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, methyl eugenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, octadeca-3,13-dien-1-yl acetate (IUPAC name) (589) + TX, orfralure (alternative name) [CCN] + TX, orictalure (alternative name) (317) + TX,ostramona (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidine (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-11-en-1-yl acetate (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B1 (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) [CCN] + TX, an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate, Petition 870190116135, dated 11 / 11 / 2019, pp. 131 / 216 122 / 200 (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquinone-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX, an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane (IUPAC / Chemical Abstracts name) (1058) + TX, 1,1-dichloro-2,2-bis(4ethylphenyl)ethane (IUPAC name) (1056), + TX, 1,2dichloropropane (IUPAC / Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1-bromo-2-chloroethane (IUPAC / Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1-(3,4dichlorophenyl)ethyl acetate (IUPAC name) (1451) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethylmethyl phosphate (IUPAC name) (1066) + TX, 2-(1,3-dithiolan-2-yl)phenyl (IUPAC / Chemical Abstracts name) (1109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC / Chemical Abstracts name) (935) + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC / Chemical Abstracts name) (1084) + TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986) + TX, 2-chlorovinyldiethylphosphate (IUPAC name) (984) + TX, 2-imidazolidone (IUPAC name) (1225) + TX, 2-isovalerilindane-1,3-dione (IUPAC name) (1246) + TX, methylcarbamate 2-methyl(prop-2-ynyl)aminophenyl (IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917) + TX, 3-methyl-1-phenylpyrazole-5-dimethylcarbamate Petition 870190116135, dated 11 / 11 / 2019, page 132 / 216, 123 / 200 ila (IUPAC name) (1283) + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name) (1285) + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPAC name) (1085) + TX, abamectin (1) + TX, acephate (2) + TX, acetamiprid (4) + TX, acetion (alternative name) [CCN] + TX, acetoprol [CCN] + TX, acrinathrine (9) + TX, acrylonitrile (IUPAC name) (861) + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, aldrin (864) + TX, allethrin (17) + TX, alosamidine (alternative name) [CCN] + TX, alixicarb (866) + TX, alphacypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminum phosphide (640) + TX, amidition (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amiton (875) + TX, amiton hydrogenoxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, atidation (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azadirachtin (alternative name) (41) + TX, azamethiphos (42) + TX, azinphos-ethyl (44) + TX, azinphosmethyl (45) + TX, nitrogenate (889) + TX,Bacillus thuringiensis delta-endotoxins (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (IUPAC / Chemical Abstracts name) (892) + TX, barthrin [CCN] + TX, Bayer 22 / 190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultape (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioallethrin (78) + TX, Scyclopentenyl isomer bioallethrin (alternative name) (79) + TX, bioethanometrin [CCN] + TX, biopermethrin (908)+ TX, Petition 870190116135, dated 11 / 11 / 2019, pp. 133 / 216 124 / 200 bioresmethrin (80) + TX, bis(2-chloroethyl) ether (name IUPAC) (909) + TX, bistrifluron (83) + TX, borax (86) + TX, brofenvalerate (alternative name) + TX, bromofenvinphos (914) + TX, bromocycline (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophosethyl (921) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, butatiophos (927) + TX, butocarboxim (103) + TX, butonate (932) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, cadusaphos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX, camfechlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (IUPAC / Chemical Abstracts name) (945) + TX, carbon tetrachloride (IUPAC name) (946) + TX, carbenothione (947) + TX, carbosulfan (119) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, cevadine (alternative name) (725) + TX, chlorbicyclolene (960) + TX, chlordane (128) + TX, chlordecone (963) + TX,chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorxifos (129) + TX, chlorfenapyr (130) + TX, chlorfenvinphos (131) + TX, chlorfluazuron (132) + TX, chlormomephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorfoxim (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, chromenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, cis-resmethrin (alternative name) + TX, cismethrin (80) + TX, clocitrin (alternative name) + TX, cloetocarb (999) + TX, closantel (name, Petition 870190116135, dated 11 / 11 / 2019, pp. 134 / 216 125 / 200 alternative) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, coumitoate (1006) + TX, crotamitone (alternative name) [CCN] + TX, crotoxifós (1010) + TX, crufomato (1011) + TX, criolita (alternative name) (177) + TX, CS 708 (código desenvolvimento) (1012) + TX, cianofenifós (1019) + TX, cianofós (184) + TX, cyanthoate (1020) + TX, cyclethrin [CCN] + TX, cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cythioate (alternative name) [CCN] + TX, d-limoneno (alternative name) [CCN] + TX, d-tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX, dazomete (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demefion (1037) + TX, demefion-O (1037) + TX, demefionS (1037) + TX, demeton (1038) + TX, demeton-methyla (224) + TX, demeton-O (1038) + TX, demeton-O-methyla (224) + TX, demeton-S (1038) + TX, demeton-S-methyla (224) + TX, demeton-S-methylsulfona (1039) + TX, diafentiuron (226) + TX, dialifós (1042) + TX, diamidafós (1044) + TX, diazinon (227) + TX, dicapton (1050) + TX,diclofenthion (1051) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicresyl (alternative name) [CCN] + TX, dicrotophos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, diethyl-5-methylpyrazol-3-yl phosphate (name IUPAC) (1076) + TX, diflubenzuron (250) + TX, dilor (alternative name) [CCN] + TX, dimefluthrin [CCN] + TX, dimefox (1081) + TX, dimetan (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinphos (265) + TX, dimethylan (1086) + TX, dinax, Petition 870190116135, dated 11 / 11 / 2019, pages 135 / 216 126 / 200 (1089) + TX, dinex-diclexin (1089) + TX, dinoprope (1093) + TX, dinosam (1094) + TX, dinosebe (1095) + TX, dinotefuran (271) + TX, diophenolan (1099) + Tzophos (1100) + TX, dioxacarbe (1101) + TX, dioxathione (1102) + TX, disulfoton (278) + TX, diticrophos (1108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX1, DX1, sterone + TX, etc. alternative) [CCN] + TX, EI 1642 (development code) (1118) + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, EMPC (1120) + TX, empenthrin (292) + TX, endosulfan (294) + TX (1121) + TX, endrine (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epophenonan (1124) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, ethaphos (alternative name) (308) + TX, ethion (309) + TX, ethiprole (310) + TX, etoate-methyl (1134) + TX, ethoprophos (312) + TX, ethyl formate (IUPAC name) [CCN] + TX, ethyl-DDD (alternate name) (+ TX, 1056)ethylene dibromo (316) + TX, ethylene dichlor (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrimfós (1142) + TX, EXD (1143) + TX, famfur (323) + TX, fenamifós (326) + TX, fenazaflor (1147) + TX, fenclorfós (1148) + TX, fenetacarb (1149) + TX, fenfluthrin (1150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1153) + TX, fenoxicarb (340) + TX, fenpyrithrin (1155) + TX, fenpropathrin (342) + TX, fenpirade (alternative name) + TX, fensulfotion (1158) + TX, fenthion (346) + TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamid (358) + TX, flubendiamide (No. Reg. CAS.: 272451-65-7) +, Petition 870190116135, dated 11 / 11 / 2019, p. 136 / 216 127 / 200 TX, flucofuron (1168) + TX, flucicloxuron (366) + TX, flucitrinato (367) + TX, fluenetil (1169) + TX, flufenorim [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1171) + TX, flumetrina (372) + TX, fluvalinato (1184) + TX, FMC 1137 (development code) (1185) + TX, fonofos (1191) + TX, formetanato (405) + TX, formetanato hydrochloride (405) + TX, formotion (1192) + TX, formparanato (1193) + TX, fosmetilan (1194) + TX, fospirato (1195) + TX, fostiazato (408) + TX, fosthiethane (1196) + TX, furatiocarb (412) + TX, furethrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, GY-81 (code development) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (1211) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hiquincarb (1223) + TX,imidacloprid (458) + TX, imiprotrin (460) + TX, indoxacarb (465) + TX, iodomethane (IUPAC name) (542) + TX, IPSP (1229) + TX, isazophos (1231) + TX, isobenzane (1232) + TX, isocarbophos (alternative name) (473) + TX, isodrine (1235) + TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxation (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmolina I (696) + TX, jasmolina II (696) + TX, iodofenphos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name, Petition 870190116135, dated 11 / 11 / 2019, pp. 137 / 216 128 / 200 alternative) [CCN] + TX, quelevane (1249) + TX, quinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin [CCN] + TX, leptophos (1250) + TX, lindane (430) + TX, lirinphos (1251) + TX, lufenuron (490) + TX, litidation (1253) + TX, m-cumenyl methylcarbamate (IUPAC name) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malathion (492) + TX, malonobene (1254) + TX, mazidox (1255) + TX, mecarbam (502) + TX, mecarfon (1258) + TX, menazone (1260) + TX, mephospholan (1261) + TX, mercurous chloride (513) + TX, mesulfenphos (1263) + TX, metaflumizone [CCN] + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methacryphos (1266) + TX, methamidophos (527) + TX, methanesulfonyl fluoride (IUPAC / Chemical Abstracts name) (1268) + TX, methidation (529) + TX, methiocarb (530) + TX, metocrotophos (1273) + TX, methomyl (531) + TX, methoprene (532) + TX, methochin-butyl (1276) + TX,methotrin (alternative name) (533) + TX, methoxychlor (534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, methofluthrin [CCN] + TX, metolcarb (550) + TX, methoxadiazone (1288) + TX, mevinfos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemicinoxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, morphation (1300) + TX, moxidectin (alternative name) [CCN] + TX, naphthalophos (alternative name) [CCN] + TX, naled (567) + TX, naphthalene (IUPAC / Chemical Abstracts name) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) +, Petition 870190116135, dated 11 / 11 / 2019, pages 138 / 216 129 / 200 TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluride (1309) + TX, nitenpyram (579) + TX, nitiazine (1311) + TX, nitrilacarb (1313) + TX, nitrilacarb 1:1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novaluron (585) + TX, noviflumuron (586) + TX, O-5-dichloro-4-iodophenyl and O-ethyl ethylphosphonothioate (IUPAC name) (1057) + TX, O,O-diethyl and phosphorothioate O-4-methyl-2-oxo-2Hchromen-7-yl (IUPAC name) (1074) + TX, phosphorothioate O,O-diethyl and O-6-methyl-2-propylpyrimidine-4-yl (IUPAC name) (1075) + TX, dithiopyrophosphate of O,O,O',O'tetrapropyl (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX (594) TX, oxamyl (602) + TX, oxidemeton-methyl (609) + TX, oxideprophos (1324) + TX, oxidissulphoton (1325) + TX, pp'-DDT (219) + TX, paradichlorobenzene [CCN] + TX, parathion (XX15) + paramethyl (609) + TX penfluron (alternative name) [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (IUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH-38 (1328) + TX, fencapton (1330) + TX, phenothrin (630) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholan (1338) + TX, phosmet (638) + TX, phosphate (139) (639) + TX, phosphine (IUPAC name) (640) + TX, phoxime (642) + TX, phoximethyl (1340) + TX, pyrimetaphos (1344) + TX, pirimicarbe (651) + TX, pyrimiphos-ethyl (1345) + TX,pirimiphos-methyl (652) + TX, isomers of polychlorodicyclopentadiene (name, IUPAC) (1346) + TX, polychloroterpenes (traditional name) Petition 870190116135, dated 11 / 11 / 2019, pp. 139 / 216 130 / 200 (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, pralethrin (655) + TX, precocene I (alternate name) [CCN] + TX, precocene II (alternate name) [CCN] + TX, precocene II (alternate name) [CCN] + TX, precocene III (alternate name) [CCN] TX, primidophos (1349) + TX, profenophos (662) + TX, profluthrin [CCN] + TX, promacil (1354) + TX, promecarbe (1355) + TX, propaphos (1356) + TX, propetamphos (673) + TX, propoxur + TX (678) (1360) + TX, prothiophos (686) + TX, protoate (1362) + TX, protriphenbut [CCN] + TX, pimetrozine (688) + TX, pyraclophos (689) + TX, pyrazophos (693) + TX, pyresmethrin (136) + pyrethrin (TX) + pyrethrin (X6,696) pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridalyl (700) + TX, pyridafenthion (701) + TX, pyrimidiphene (706) + TX, pyrimitate (1370) + TX, pyriproxyphenone (708) + TX (alternative nomenclature) [CCN] + TX, quinalphos (711) + TX, quinalphos-methyl (1376) + TX, quinothion (1380) + TX, quinthiophos (1381) + TX,R-1492 (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, ryania (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (alternative name) (725) + TX, scandane (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) compound) + TX, SI-0405 (compound code) + TX, silafluophene (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (name, Petition 870190116135, dated 11 / 11 / 2019, pages 140 / 216 131 / 200 IUPAC / Chemical Abstracts) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (IUPAC name) (1401) + TX, sodium thiocyanate [CCN] + TX, somamide (1402) + TX, spinosad (737) + TX, spiromesifen (739) + TX, spirotetramate [CCN] + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramide (750) + TX, sulfotepe (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrad (763) +TX, tebupirinphos (764) + TX, teflubenzuron (768) +TX, tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, teralethrin (1418) + TX, terbam (alternative name) + TX, terbufós (773) + TX, tetrachloroethane [CCN] +TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, tetacypermethrin (204) + TX, thiacloprid (791) + TX, tiafenox (alternative name) + TX, thiamethoxam (792) + TX,ticrophos (1428) + TX, thiocarboxime (1431) + TX, thiocyclam (798) + TX, thiocyclam hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiophanox (800) + TX, thiometon (801) + TX, thionazine (1434) + TX, thiosultape (803) + TX, thiosultapesodium (803) + TX, thuringiensin (alternative name) [CCN] + TX, tolfenpyrad (809) + TX, tralomethrin (812) + TX, transfluthrin (813) + TX, transpermethrin (1440) + TX, triamiphos (1441) + TX, triazamate (818) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trichlormetaphos-3 (alternative name) [CCN] + TX, trichloronate (1452) + TX, tripenophos (1455) + TX, triflumuron (835) + TX, trimetacarb (840) + TX, triprene, Petition 870190116135, dated 11 / 11 / 2019, pp. 141 / 216 132 / 200 (1459) + TX, vamidothion (847) + TX, vaniliprole [CCN] + TX, veratridine (alternative name) (725) + TX, veratrine (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zetamethrin (alternative name) + TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprole [736994-63-19] + TX, chlorantraniliprole [500008-45-7] + TX, cienopirafen [560121-52-0] + TX, cyflumetofen [400882-07-7] + TX, pyrifluquinazon [337458-27-2] + TX, spinetoram [187166-401 + 187166-15-0] + TX, spirotetramate [203313-25-1] + TX, sulfoxaflor [946578-00-3] + TX, flufiprol [704886-18-0] + TX, meperfluthrin [915288-13-0] + TX, tetramethylfluthrin [84937-88-2] + TX, a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, chloretocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, trifenmorph (1454) + TX, trimetacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprole [394730-71-3] + TX, a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1,2 Petition 870190116135, dated 11 / 11 / 2019, pages 142 / 216 133 / 200 dibromo-3-cloropropano (nome da IUPAC / Chemical Abstracts) (1045) + TX, 1,2-dicloropropano (nome IUPAC / Chemical Abstracts) (1062) + TX, 1,2-dichloropropane with 1,3dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 1,1-dichlorotetrahydrothiophene dioxide (IUPAC / Chemical Abstracts name) (1065) + TX, 3-(4chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprol [CCN] + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, AZ 60541 (compound code) + TX, benclotiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, cadusaphos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, cloetocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidaphos (1044) + TX, diclofenthion (1051) + TX, diclyphos (alternative name) + TX,dimethoate (262) + TX, doramectin (alternate name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternate name) [CCN] + TX, ethoprophos (312) + TX, ethylene dibromide (316) (326) + TX, fenpyrade (alternate name) + TX, fensulfothion (1158) + TX, phosthiazate (408) + TX, phostiethane (1196) + TX, furfural (alternate name) [CCN] + TX, GY-81 (development code) (423) + heterologous TX, N TX, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazophos (1231) + TX, ivermectin (alternate name) [CCN], Petition 870190116135, of 11 / 11 / 2019, p. 143 / 216 134 / 200 + TX, kinetin (alternative name) (210) + TX, mecarfon (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, Myrothecium verrucaria composition (alternative name) (565) + TX, NC184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosphocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC / Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazine (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1] + TX, a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapirin (580) + TX, a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX, a rodenticide selected from the group of substances consisting of 2-isovalerilindan-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, antu (880) + TX, oxide Petition 870190116135, dated 11 / 11 / 2019, pp. 144 / 216 135 / 200 arsenious (882) + TX, barium carbonate (891) + TX, bistiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuril (1005) + TX, coumateryl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difethialone (249) + TX, difacinone (273) + TX, ergocalciferol (301) + TX, flocoumaphene (357) +TX, fluoroacetamide (379) + TX, flupropadine (1183) +TX, flupropadine hydrochloride (1183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) +TX, iodomethane (IUPAC name) (542) + TX, lindane (430) +TX, magnesium phosphide (IUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, phosacetim (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, sciliroside (1390) + TX,sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX, a synergistic agent selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, butoxide of piperonyl (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, Petition 870190116135, dated 11 / 11 / 2019, pages 145 / 216 136 / 200 S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX, an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4amine (IUPAC name) (23) + TX, thiram (804) + TX, trimetacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX, a virucide selected from the group of substances consisting of imanine (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX, a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octilinone (590) and thiophanate-methyl (802) + TX, and biologically active compounds selected from the group consisting of azaconazole (60207-31-0] + TX, bitertanol [70585-36-3] + TX,bromuconazol [116255-48-2] + TX, ciproconazol [94361-06-5] + TX, difenoconazol [119446-68-3] + TX, diniconazol [83657-24-3] + TX, epoxiconazol [10632508-0] + TX, fenbuconazol [114369-43-6] + TX, fluquinconazol [136426-54-5] + TX, flusilazol [85509-19-9] + TX, flutriafol [76674-21-0] + TX, hexaconazol [79983-71-4] + TX, imazalil [35554-44-0] + TX, imibenconazol [86598-92-7] + TX, ipconazol [125225-28-7] + TX, metconazol [125116-236] + TX, miclobutanil [88671-89-0] + TX, pefurazoato [101903-30-4] + TX, penconazol [66246-88-6] + TX, protioconazol [178928-70-6] + TX, pirifenox [88283-41-4] +, Petição 870190116135, de 11 / 11 / 2019, pág. 146 / 216 137 / 200 TX, procloraz [67747-09-5] + TX, propiconazole [60207-90-1] + TX, simeconazole [149508-90-7] + TX, tebuconazole [10753496-3] + TX, tetraconazole [112281-77-3] + TX, triadimefon [43121-43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] + TX, triticonazole [131983-72-7] + TX, ancimidol [12771-68-5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71-9] + TX, bupirimate [41483-43-6] + TX, dimethylmol [5221-53-4] + TX, etirimol [23947-60-6] + TX, dodemorph [1593-77-7] + TX, fenpropidine [67306-00-7] + TX, fenpropimorph [67564-91-4] + TX, spiroxamine [11813430-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552-61-2] + TX, mepanipirim [110235-47-7] + TX, pyrimethanil [53112-28-0] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [131341-86-1] + TX, benalaxil [71626-11-4] + TX, furalaxyl [57646-30-7] + TX, metalaxyl [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX,carbendazim [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-79-8] + TX, clozolina [84332-86-5] + TX, diclozolin [24201-58-9] + TX, iprodione [36734-19-7] + TX, myclozolin [54864-61-8] + TX, procimidone [32809-16-8] + TX, vinclozolin [50471-448] + TX, boscalid [188425-85-6] + TX, carboxin [5234-684] + TX, fenfuram [24691-80-3] + TX, flutolanil [66332-965] + TX, mepronil [55814-41-0] + TX, oxycarboxin [5259-881] + TX, penthiopyrad [183675-82-3] + TX, thifluzamide [130000-40-7] + TX, guazatine [108173-90-6] + TX, dodine [2439-10-3] [112-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, dimoxystrobin [149961-52-4] + TX, enostroburin {Proc., Petition 870190116135, dated 11 / 11 / 2019, p. 147 / 216 138 / 200 BCPC, Int. Congr., Glasgow, 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX, kresoxim-methyl [14339089-0] + TX, metominostrobin [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, oryzastrobin [24859316-0] + TX, picoxystrobin [117428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, ferbam [14484-64-1] + TX, mancozeb [8018-01-7] + TX, maneb [12427-38-2] + TX, they messed up [9006-42-2] + TX, propineb [12071-83-9] + TX, thiram [137-26-8] + TX, zineb [12122-67-7] + TX, ziram [137-30-4] + TX, captafol [2425-06-1] + TX, captan [13306-2] + TX, diclofluanide [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folpet [133-07-3] + TX, tolylfluanide [731-27-1] + TX, Bordeaux mixture [8011-63-0] + TX, copper hydroxide [20427-59-2] + TX, copper oxychloride [1332-40-7] + TX, copper sulfate [7758-98-7] + TX, copper oxide [1317-39-1] + TX, mancobre [53988-93-5] + TX, copper oxine [10380-28-6] + TX, dinocape [131-72-6] + TX, nitrotal-isopropyl [10552-74-6] + TX,edifenphos [17109-498] + TX, iprobenfos [26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdifen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclophos-methyl [57018-04-9] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-053] + TX, bentiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, quinomethionate [2439-01-2] + TX, chloroneb [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamide [180409-60-3] + TX, cymoxanil [57966-95-7] ​​+ TX, diclone [117-80-6] + TX, diclocimet [139920-32-4] + TX, diclomezine [62865-36-5] + TX, dichloran [99-30-9] + TX, diethofencarb [87130-20-9] + TX, dimethomorph [110488-70-5] + TX, SYP-LI90 (Flumorph) [211867-47-9] + TX, dithianon, Petition 870190116135, dated 11 / 11 / 2019, pp. 148 / 216 139 / 200 [3347-22-6] + TX, etaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [131807-57-3] + TX, phenamidone [161326-34-7] + TX, phenoxanil [115852-48-7] + TX, fentin [668-34-8] + TX, ferimzone [89269-64-7] + TX, fluazinam [79622-59-6] + TX, fluopicolide [239110-15-7] + TX, flusulfamide [106917-52-6] + TX, fenhexamide [126833-17-8] + TX, fosetyl aluminum [39148-24-8] + TX, himexazol [1000444-1] + TX, iprovalicarb [140923-17-7] + TX, IKF-916 (Ciazofamide) [120116-88-3] + TX, casugamicin [6980-18-3] + TX, metasulfocarb [66952-49-6] + TX, metrafenone [220899-03-6] + TX, pencycuron [66063-05-6] + TX, phthalide [27355-22-2] + TX, polyoxins [11113-80-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazide [189278-12-4] + TX, piroquilon [57369-32-1] + TX, quinoxifene [124495-18-7] + TX, quintazene [82-68-8] + TX, sulfur [7704-34-9] + TX, thiadinil [223580-51-6] + TX, triazoxide [72459-58-6] + TX, tricyclazole [41814-78-2] + TX, triforin [26644-46-2] + TX, validamycin [37248-47-8] + TX, zoxamide (RH7281) [156052-68-5] + TX, mandipropamide [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, sedaxane [874967-67-6] + TX, (9-dichloromethylene-1,2,3,4-tetrahydro1,4-methane-naphthalen-5-yl)-3-difluoromethyl-1methyl-1H-pyrazol-4-carboxylic acid amide (disclosed in WO 2007 / 048556) + TX, [2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (disclosed in WO 2008 / 148570) + TX, 1-[4-[4[(5S)5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3(trifluoromethyl)-1H-pyrazol-1-yl]ethanone + TX, 1-[4-[4-[5(2,6-difluorophenyl)-4,5-dihydroa-1,3-ylzol]-oxa Petition 870190116135, dated 11 / 11 / 2019, p. 149 / 216 140 / 200 2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1Hpyrazol-1-yl]ethanone [1003318-67-9], both disclosed in WO 2010 / 123791, WO 2006 / 8 / 0139250 WO13925 2011 / 051243 page 20) +TX, (3',4',5'-trifluoro-biphenyl-2yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazol-4carboxylic acid (disclosed in WO 2003, TX +43 / 087 1-methyl2-(2,4,5-trichloro-thiophen-3-yl)-ethyl] + TX.

[0274] The parenthetical references after the active ingredients, for example, [3878-19-1] refer to the Chemical Abstracts Registration Number. The mixing partners described above are known. When the active ingredients are included in The Pesticide Manual [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: CDS TomLin; The British Crop Protection Council], they are described therein under the entry number given in parentheses above in this document for the particular compound; for example, the compound abamectin is described under entry number (1). When [CCN] is added above in this document to the particular compound, the compound in question is included in the Compendium of Pesticide Common Names, which is accessible via the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; For example, the compound acetoprole is described at the internet address http: / / www.alanwood.net / pesticides / acetoprole.html.

[0275] Most of the active ingredients described above are referred to previously by a so-called common name, being the relevant ISO common name or another common name used in individual cases. If the designation is not a common name, the nature of the alternative designation used is Petition 870190116135, dated 11 / 11 / 2019, pages 150 / 216 141 / 200 given in parentheses for the particular compound; in this case, the IUPAC name, the IUPAC / Chemical Abstracts name, a chemical name, a traditional name, a compound name, or a development code is used, or, if none of these designations nor a common name is used, an alternative name is used. No. Reg. Cas means the Chemical Abstracts Registration Number.

[0276] The mixture of active ingredients of the compounds of formula I or of a specific compound selected from Tables 1 to 126 or Table B, and of an active ingredient as described above preferably consists of a mixing ratio from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio from 20:1 to 1:20, even more especially from 10:1 to 1:10, most especially between 5:1 and 1:5, special preference being given to a ratio from 2:1 to 1:2, and a ratio from 4:1 to 2:1 being equally preferred, above all a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750.These mixing ratios are understood to include, on the one hand, weight ratios, and also, on the other hand, molar ratios.

[0277] The mixtures as described above may be used in a method for pest control, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception Petition 870190116135, dated 11 / 11 / 2019, pages 151 / 216 142 / 200 of a method for treating the human or animal body by surgery or therapy, and diagnostic methods practiced on the human or animal body.

[0278] Mixtures comprising a compound of formula I or a specific compound selected from Tables 1 to 126 or Table B and one or more active ingredients as described above may be applied, for example, in a single ready-to-mix form, in a combined spray mixture composed of separate formulations of the components of the individual active ingredients, such as a mixing tank, and in a combined use of the individual active ingredients when applied sequentially, i.e., one after the other, within a reasonably short period, such as a few hours or days. The order of application of the compounds of formula I or of a specific compound selected from Tables 1 to 126 or Table B, and of the active ingredients as described above is not essential for carrying out the present invention.

[0279] The compositions may also comprise additional solid or liquid auxiliaries such as stabilizers, for example epoxidized or non-epoxidized vegetable oils (for example epoxidized soybean oil, rapeseed oil or coconut oil), antifoaming agents, for example silicone oil, preservatives, viscosity regulators, binders and / or tack promoters, fertilizers or other active ingredients to achieve specific effects, for example bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0280] The compositions according to the invention are Petition 870190116135, dated 11 / 11 / 2019, pages 152 / 216 143 / 200 prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, sieving and / or compressing a solid active ingredient and in the presence of at least one auxiliary, for example by intimate mixing and / or grinding of the active ingredient with the auxiliary (auxiliaries). These processes for preparing the compositions and the use of compounds I for preparing these compositions are also a subject of the invention.

[0281] The application methods for the compositions, that is, the pest control methods of the type mentioned above, such as spraying, atomizing, dusting, brushing, covering, scattering or pouring – which are to be selected so as to suit the desired objectives of the prevailing circumstances – and the use of the compositions for pest control of the type mentioned above, are other subjects of the invention. Typical concentration rates are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. The application rate per hectare is generally from 1 to 2000 g of active ingredient per hectare, in particular from 10 to 1000 g / ha, preferably from 10 to 600 g / ha.

[0282] A preferred method of application in the area of ​​crop protection consists of application to the foliage of plants (foliar application), making it possible to select the frequency and rate of application corresponding to the risk of infestation with the pest in question. Alternatively, the active ingredient can reach the plants through the root system (systemic action), by soaking the plant locus with a liquid composition or by Petition 870190116135, dated 11 / 11 / 2019, pages 153 / 216 144 / 200 incorporation of the active ingredient in solid form at the plant site, for example in the soil, for example in the form of granules (soil application). In the case of rice paddies, such granules can be applied to the flooded rice paddy.

[0283] The compositions according to the invention are also suitable for protecting plant propagation material, for example seeds, such as fruit, tubers or nuclei, or nursery plants, against pests of the type mentioned above. The propagation material can be treated with the compositions before planting, for example the seed can be treated before sowing. Alternatively, the compositions can be applied to the seed nuclei (coating), either by soaking the nuclei in a liquid composition, or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted at the application site, for example in the seed furrow during the row formation process. These methods of treatment for the plant propagation material, and the plant propagation material thus treated, are further subjects of the invention.

[0284] The compounds of formula (I) according to the invention can also be used in combination with plant protection agents. Preferably, in these mixtures, the compound of formula (I) or a specific compound selected from Tables 1 to 126 or Table B. The following mixtures with plant protection agents are considered in particular: compound of formula (I) + cloquintocete-mexil, Petition 870190116135, dated 11 / 11 / 2019, pp. 154 / 216 145 / 200 compound of formula (I) + cloquintocet acid and its salts, compound of formula (I) + fenchlorazole-ethyl, compound of formula (I) + fenchlorazole acid and its salts, compound of formula (I) + mefenpyr-diethyl, compound of formula (I) + mefenpyr diacid, compound of formula (I) + isoxadifen-ethyl, compound of formula (I) + isoxadifen acid, compound of formula (I) + furilazole, compound of formula (I) + furilazole R isomer, compound of formula (I) + benoxacor, compound of formula (I) + dichlormide, compound of formula (I) + AD-67, compound of formula (I) + oxabetrinil, compound of formula (I) + ciometrinil, compound of formula (I) + ciometrinil Z isomer, compound of formula (I) + fenclorim, compound of formula (I) + cyprosulfamide, compound of formula (I) + naphthalic anhydride, compound of formula (I) + flurazole, compound of formula I + N-(2-methoxybenzoyl)-4[(methylaminocarbonyl)amino]benzenesulfonamide, compound of formula (I) + CL 304,415,compound of formula (I) + dicyclonone, compound of formula (I) + fluxofenim, compound of formula (I) + DKA-24, compound of formula (I) + R-29148 and compound of formula (I) + PPG-1292. A phytoprotective effect can also be observed for the mixtures compound of formula (I) + dimron, compound of formula (I) + MCPA, compound of formula (I) + mecoprope and compound of formula (I) + mecoprope-P.

[0285] TX mixing partners may also be in the form of esters or salts, as mentioned, for example, in The Pesticide Manual, 12th Edition (BCPC), 2000.

[0286] In the different lists above of active ingredients to be mixed with a TX, the compound with formula I is of Petition 870190116135, dated 11 / 11 / 2019, pp. 155 / 216 146 / 200 preference a specific compound selected from Table 1 to 126 or from Table B.

[0287] In the above-mentioned mixtures of compounds of formula I, in particular a specific compound selected from Table 1 to 126 or from Table B, with other insecticides, fungicides, herbicides, plant protectants, adjuvants and the like, the mixing ratios may vary within a wide range, preferably from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially from 20:1 to 1:20, even more especially from 10:1 to 1:10. These mixing ratios are understood as including, on the one hand, weight ratios, and also, on the other hand, molar ratios.

[0288] Mixtures can advantageously be used in the formulations mentioned above (and in this case, “active ingredient” refers to the respective mixture of TX with the mixing partner).

[0289] Some mixtures may comprise active ingredients that have significantly different physical, chemical, or biological properties, such that they do not readily lead by themselves to the same type of conventional formulation. In these circumstances, other types of formulations may be prepared. For example, when one active ingredient is a water-insoluble solid and the other a water-insoluble liquid, it may still be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of a SC), but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resulting composition is a suspoemulsion formulation. Petition 870190116135, dated 11 / 11 / 2019, pages 156 / 216 147 / 200 (SE) .

[0290] Mixtures comprising a specific TX compound selected from Table 1 to 126 or Table B and one or more active ingredients as described above may be applied, for example, in a single ready-to-mix form, in a combined spray mixture composed of separate formulations of the individual active ingredient components, such as a mixing tank, and in a combined use of the individual active ingredients when applied sequentially, i.e., one after the other, within a reasonably short period, such as a few hours or days.

[0291] The compounds of formula (I) can be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.

[0292] Examples of suitable synergistic agents for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

[0293] The herbicides and plant growth regulators suitable for inclusion in the compositions will depend on the intended target and the required effect.

[0294] An example of a selective herbicide for rice that could be included is propanil. An example of a plant growth regulator for use in cotton is PIX™.

[0295] Some mixtures may comprise active ingredients that have significantly different physical, chemical, or biological properties, so that they do not readily lead by themselves to the same type of Petition 870190116135, dated 11 / 11 / 2019, pp. 157 / 216 148 / 200 conventional formulation. Under these circumstances, other types of formulations can be prepared. For example, when one active ingredient is a water-insoluble solid and the other a water-insoluble liquid, it may still be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of a SC), but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resulting composition is a suspoemulsion (SE) formulation.

[0296] The following Examples illustrate, but do not limit, the invention.

[0297] The compounds of the invention can be distinguished from known compounds by virtue of greater effectiveness at low application rates, which can be verified by a person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example, 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.8 ppm. Preparatory Examples Examples

[0298] The following abbreviations have been used throughout this section: s = singlet; bs = wide singlet; d = doublet; dd = double doublet; dt = double triplet; t = triplet, tt = triple triplet, q = quartet, sept = septet; m = multiplet; Me = methyl; Et = ethyl; Pr = propyl; Bu = butyl; Pf = melting point; EtOAc = Ethyl acetate; TBME = tert-butyl methyl ether Example P1:N- [3- [ [2-bromo-4- [1Petition 870190116135, of 11 / 11 / 2019, page 158 / 216 149 / 200 [bromo(difluoro)methyl]-1,2,2,2-tetrafluoro-ethyl]-6-chlorophenyl]carbamoyl]-2-methoxy-phenyl]pyridine-4-carboxamide (Table B Entry 3) Step 1: 4-[1-[bromo(difluoro)methyl]-1,2,2,2- [02 99] Aniline (40 g, 425 mmol) was dissolved in 670 mL of TBME and 470 mL of water, and treated with sodium dithionite (102 g, 510 mmol), tetrabutylammonium hydrogen sulfate (11.6 g, 34 mmol), and sodium bicarbonate (42.9 g, 510 mmol, 1.2 eq.). The yellow emulsion was treated dropwise with 1,2-Dibromo-1,1,2,3,3,3-hexafluoropropane (72.9 mL, 510 mmol, prepared as described in Eur. Pat. Appl., 1418163) maintaining the temperature below 250 °C, with vigorous stirring. After the addition, the reaction was stirred for another 3 hours, the organic phase separated, and the aqueous phase extracted again (x3) with tert-butylmethyl ether. The combined organic phases were washed with saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo to yield 46 g (33%) of the compound described above as a dark brownish oil, which was used in the next step without purification. Petition 870190116135, dated 11 / 11 / 2019, pages 159 / 216 150 / 200 additional.

[0300] 1H RMN (400 MHz, CDCI3, δ em ppm): 7.36-7.43 (d, J=8.4 Hz, 1H); 6.78 (d, J=8.4 Hz, 1H); 4,14 (sl, 2H) Etapa 2.: 2-bromo-4-[1-[bromo(difluoro)metil]-ddd-tetrxiucrc-et' / sni'ns

[0301] 4-[1-[bromo(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]aniline (46.0 g, 136 mmol) was dissolved in DMF (370 mL) and treated in small portions with N-bromosuccinimide (25.1 g, 138 mmol), while the reaction temperature was maintained below 30 °C. The mixture was stirred at room temperature until TLC analysis after 3 hours showed that the reaction was complete. The reaction mixture was diluted with TBME and water, the organic phase separated, and the aqueous phase extracted again with 2 x 100 mL of tert-butylmethyl ether. The combined organic phases were washed with water, saturated sodium chloride solution, dried with Na2SO4, filtered, and concentrated under vacuum. This resulted in 62 g of the aforementioned compound (containing a small amount of DMF) as a brown oil which was used in the next step without further purification.

[0302] 1H NMR (400 MHz, CDCl3, δ in ppm): 7.64 (s, 1H); 7.32 (d, J=8.4 Hz, 1H); 6.81 (d, J=8.4Hz, 1H); 3.36 (s l. 2H). Step 3: 2-bromo-4-[1-[bromo(difluoro)methyl]1,2,2,2-tetrafluoro-ethyl]-6-chloro-aniline: Petition 870190116135, dated 11 / 11 / 2019, pages 160 / 216 151 / 200

[0303] A solution of 2-bromo-4-[1[bromo(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]aniline (62 g, 139 mmol) in DMF (450 mL) was treated with N-chlorosuccinimide (19.9 g, 146 mmol), and the mixture was heated to 70 °C. An LCMS after 2 hours showed that the reaction was complete. The reaction mixture was diluted with TBME and water, the organic phase separated, and the aqueous phase extracted again with 2 x 100 mL of TBME. The combined organic phases were washed with water, saturated sodium chloride solution, dried with Na2SO4, filtered, and concentrated in vacuo to yield 59.2 g of a brown oil, which was purified using a silica gel cartridge (Torrent) eluting with 100:0 --> 50:50 heptane / EtOAc. This yielded the compound in epigraph (46 g, 76%) as a pale brown oil.

[0304] 1H NMR (400 MHz, CDCl3, δ in ppm): 7.60 (s, 1H); 7.46 (s, 1H); 4.78 (sl, 2H). Step 4: N-[2-bromo-4-[1-[bromo(difluoro)methyl]1,2,2,2-tetrafluoro-ethyl]-6-chloro-phenyl]-2-fluoro-3-nitrobenzamide Petition 870190116135, dated 11 / 11 / 2019, pages 161 / 216 152 / 200

[0305] A solution of 2-bromo-4-[1[bromo(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6-chloroaniline (46 g, 104 mmol) and potassium iodide (4.3 g, 25.9 mmol) was dissolved in acetonitrile (460 mL). 2-fluoro-3-nitrobenzoyl chloride (45.8 g, 207 mmol) was added to this solution, prepared as described in J. Amer. Chem. Soc, 135(26), (9675, 2013) and the mixture was heated to 82 °C overnight. An LCMS after this period showed that the reaction was complete. The mixture was diluted with 400 mL of dichloromethane, inactivated with NaHSO3 solution, and extracted with 2 x 250 mL of dichloromethane. The combined organic phases were washed with saturated sodium chloride solution, dried with Na2SO4, filtered, and evaporated to give 86 g of impure product as a yellow resin. Purification using a silica gel cartridge (Torrent) eluting with Heptane / EtOAc 100:0 --> 50:50 yielded 62 g (100%) of the compound described above as pale yellow crystals.

[0306] 1H NMR (400 MHz, CDCl3, δ in ppm): 8.44-8.54 (m, 1H); 8.28 (td, J=7.7, 1.8 Hz, 1H), 8.14 (d, J=12.1 Hz, 1H); 7.86 (s, 1H), 7.74 (s, 1H), 7.53 (t, J=8.1 Hz, 1H).

[0307] LCMS: (Method ZDQ13): 599, 601 (M + H), 603, retention time 1.17 min Step 5: N-[2-bromo-4-[1-[bromo(difluoro)methyl]1,2,2,2-tetrafluoroethyl]-6-chlorophenyl]-2-methoxy-3-nitro Petition 870190116135, dated 11 / 11 / 2019, page 162 / 216 153 / 200 benzamide

[0308] A solution of N-[2-bromo-4-[1[bromo(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6-chlorophenyl]-2-fluoro-3-nitrobenzamide (62 g, 102 mmol) was dissolved in MeOH (450 mL) and treated with a solution of sodium methoxide in methanol (5.4 mol / L, 29 mL, 158 mmol) at room temperature. The mixture was stirred at room temperature until an LCMS / TLC showed that the reaction was complete. The reaction mixture was diluted with 100 mL of water and stirred for 6 hours at room temperature. Then, the mixture was evaporated, the residue dissolved in EtOAc, and the EtOAc solution washed with saturated sodium chloride solution, the organic phase dried with Na2SO4, filtered, and concentrated in vacuo. The impure product was used in the next step without further purification.

[0309] 1H NMR (CDCls, 400MHz): δ (ppm) 9.22 (s, 1H); 8.45 (dd, J=7.7, 1.8 Hz, 1H); 8.08 (dd, J=8.1, 1.8 Hz, 1H); 7.86 (s, 1H); 7.74 (s, 1H); 7.45 (t, J=8.1 Hz, 1H); 7.27 (s, 1H); 4.12 (s, 3H).

[0310] LCMS: (ZDQ13 Method): 611, 613 (M + H), 615, retention time 1.18 min Step 6:3-amino-N-[2-bromo-4-[1[bromo(difluoro)methyl]-1,2,2,2-tetrafluoro-ethyl]-6-chlorophenyl]-2-:methoxy-benzamide Petition 870190116135, dated 11 / 11 / 2019, pp. 163 / 216 154 / 200

[0311] This was N-[2-bromo-4-[1-[bromo(difluoro)methyl] [1,2,2,2-tetrafluoroethyl]-6-chlorophenyl]-2-methoxy-3-nitrobenzamide (5.6 g, 8.4 mmol) was dissolved in isopropanol (120 mL) with anhydrous tin chloride (5.7 g, 30 mmol), and then added dropwise with concentrated hydrochloric acid (8 mL) at room temperature. The mixture was then heated to 90 °C for 1 hour, after which an LCMS / TLC showed that the reaction was complete. The mixture was poured over water, adjusted to pH 10 with 2N NaOH, and extracted with 3 x 100 mL of EtOAc. The combined organic phases were washed with saturated sodium chloride solution, dried with MgSO4, filtered, and concentrated under vacuum. Purification using a silica gel cartridge (Rf200) eluting with Cyclohexane / EtOAc 95:5 --> 60:40 gave the compound described above (4.6 g, 94%) as a brownish resin:

[0312] 1H NMR (400 MHz, CDCl3, δ in ppm): 9.53 (s, 1H); 7.84 (s, 1H); 7.72 (s, 1H), 7.59 (dd, J=7.7, 1.8 Hz, 1H); 7.12 (t, J=7.7 Hz, 1H); 7.01 (dd, J=7.9, 1.7 Hz, 1H); 4.18 (sl, 2H); 4.01 (s, 3H).

[0313] LCMS: (ZDQ13 Method): 583, 585 (M + H), 587, retention time 1.14 min Step 7: N-[3-[[2-bromo-4-[1[bromo(difluoro)methyl]-1,2,2,2-tetrafluoro-ethyl]-6-chlorophenyl]carbamoyl]-2-methoxyphenyl]pyridine-4-carboxamide Petition 870190116135, dated 11 / 11 / 2019, pages 164 / 216 155 / 200

[0314] To a solution of 3-amino-N-[2-bromo-4-[1[bromo(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6-chlorophenyl]-2-methoxybenzamide (83 mg, 0.14 mmol) and pyridine (45 μL, 0.55 mmol) in THF (4 mL) was added pyridine-4-carbonyl chloride hydrochloride (28 mg, 0.15 mmol). The mixture was stirred at room temperature and monitored by TLC / LCMS. After 23 hours, approximately 20% of the starting material was still present, and thus more pyridine-4-carbonyl chloride hydrochloride (25 mg, 0.14 mmol) was added. After the reaction was complete, the mixture was inactivated with water and saturated NaHCO3 solution, and extracted with 2 x 20 mL of EtOAc. The combined organic phases were washed with a saturated sodium chloride solution, dried with Na2SO4, filtered, and concentrated under vacuum.

[0315] The impure product was purified using a silica gel cartridge (Rf200) eluting with Cyclohexane / EtOAc 10:90 --> 0:100 to give the compound in epigraph (87 mg, 93%) as a pale yellow resin.

[0316] 1H NMR (400 MHz, CDCl3, δ in ppm): 9.03 (s, 1H); 8.89 (d, J=4.9 Hz, 2H); 8.69 (dd, J=8.1, 1.5 Hz, 1H); 8.51 (s, 1H); 7.96 (dd, J=7.9, 1.7 Hz, 1H); 7.86 (s, 1H); 7,747.81 (m, 3H); 7.41 (t, J=8.1 Hz, 1H); 4.09 (s, 3H).

[0317] LCMS: (ZDQ13 Method): 688, 690 (M + H), 692, retention time 1.10 min Example P2: Step 2: N- [2-bromo-4- [1 Petition 870190116135, dated 11 / 11 / 2019, page 165 / 216 156 / 200 [bromo(difluoro)methyl]-1,2,2,2-tetrafluoro-ethyl]-6-chlorophenyl]-3-[(4-cyanobenzoyl)-ethyl-amino]-2-:methoxy-benzamide (Entry 1 in Table B) Step 1: N-[2-bromo-4-[1-[bromo(difluoro)methyl]1,2,2,2-tetrafluoro-ethyl]-6-chloro-phenyl]-3-(ethylamino)-2methoxy-benzamide

[0318] A solution of N-[2-bromo-4-[1[bromo(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6-chlorophenyl]-2-methoxy-3-nitrobenzamide (5.0 g, 8.1 mmol, Step 6, Example P1), acetaldehyde (0.61 mL, 10.6 mmol), and acetic acid (0.61 mL, 10.6 mmol) in MeOH (100 mL) was treated with sodium cyanoborohydride (699 mg, 10.6 mmol) at room temperature. The resulting mixture was stirred at room temperature and after 4 hours, LCMS showed complete conversion. The mixture was concentrated in vacuo, the residue inactivated with 25 mL of water, and extracted with 3 x 50 mL of dichloromethane. The combined organic phases were washed with water, saturated sodium chloride solution, dried with Na2SO4, filtered, and concentrated under vacuum. Purification using a silica gel cartridge (Rf200) eluting with dichloromethane / MeOH yielded the compound described above (4.8 g, 96%) as dirty white crystals.

[0319] 1H NMR (400 MHz, CDCl3, δ in ppm): 9.49 (s, 1H); 7.84 (s, 1H); 7.72 (s, 1H); 7.48 (dd, J=7.7, 1.5 Hz, 1H); 7.18 (t, J=7.9 Hz, 1H); 6.89 (dd, J=8.1, 1.5 Hz, 1H); 4.17 Petition 870190116135, dated 11 / 11 / 2019, pp. 166 / 216 157 / 200 (sl, 1H), 3.97 (s, 3H); 3.24 (q, J=7.0 Hz, 2H); 1.35 (t, J=7.2 Hz, 3H).

[0320] LCMS: (ZDQ13 Method): 611, 613 (M + H), 615, retention time 1.27 min Step 2: N-[2-bromo-4-[1-[bromo(difluoro)methyl]1,2,2,2-tetrafluoro-ethyl]-6-chloro-phenyl]-3-[(4cyanobenzoyl)-ethyl-amino]-2-methoxy-benzamide

[0321] 4-Cyanobenzoyl chloride (105 mg, 0.615 mmol) was added to a solution of N-[2-bromo-4-[1[bromo(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6-chlorophenyl]-3-(ethylamino)-2-methoxybenzamide (353 mg, 0.559 mmol) and pyridine (183 μL, 2.24 mmol) in THF (15 mL). The mixture was stirred at room temperature and monitored by TLC / LCMS. After the reaction was complete, the reaction mixture was inactivated with water and saturated NaHCO3 solution, and extracted with 2 x 20 mL of EtOAc. The combined organic phases were washed with saturated sodium chloride solution, dried with Na2SO4, filtered, and evaporated.

[0322] Purification using a silica gel cartridge (Rf200) eluting with Cyclohexane / EtOAc 100:0 --> 60:40 gave the compound described above (368 mg, 89%) as a white foam.

[0323] 1H NMR (400 MHz, CDCla, δ in ppm): Selected signals, rotamere mix: 8.05 (d, J=7.7 Hz); 7.81 (s), 7.70 (s);7.38-7.63 (m), 3.52-4.57 (m); 1.11-1.69 Petition 870190116135, dated 11 / 11 / 2019, pp. 167 / 216 158 / 200 (m) .

[0324] LCMS: (ZDQ13 Method): 740, 742 (M + H), 744, retention time 1.20 min Example P3: N-[3-[[2-bromo-4-[1[chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6-(difluoromethoxy)phenyl]carbamoyl]-2-methoxyphenyl]-Netyl-1-oxidopyridin-1-io-4-carboxamide (Entry 44 of Table B)

[0325] A colorless solution of N-[3-[[2-bromo-4-[1[chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6(difluoromethoxy)phenyl]carbamoyl]-2-methoxyphenyl]-N-ethylpyridine-4-carboxamide (Entry 36 of Table B) (0.095 g) in dichloromethane (3.0 mL) was treated with 0.040 g of 70% meta-chloroperbenzoic acid. After 16 hours of stirring at 20 °C, complete conversion was observed by LC-MS and TLC analysis. The reaction mixture was washed with an aqueous solution of sodium sulfite, and then twice with an aqueous solution of sodium bicarbonate. The organic phase was dried with sodium sulfate and evaporated to yield the compound in question as a white powder, with a melting range of 109–228 °C.

[0326] 1H NMR (400 MHz, CDCl3, δ in ppm): 8.60 (sl, 1H), 8.05 (d, J = 8.1 Hz, 1H), 7.97 (dl, 2H), 7.78 (s, 1H), 7.53 (d, J = 8.1 Hz, 1H), 7.49 (s, 1H), 7.8 (t, J = Petition 870190116135, dated 11 / 11 / 2019, pp. 168 / 216 159 / 200 8,1 Hz, 1H), 7,20 (d l, 2H), 6,61 (t, J = 73 Hz, 1H), 4,30 (m l, 1H), 3,91 (s, 3H), 3,75 (m l, 1 H), 1,41 (t l, 3H). Exemplo P4: N-[3-[[2-bromo-6-(difluorometoxi)-4[1,2,2,2-tetrafluoro-1(trifluorometil)etil]fenil]carbamoil]-2-metoxi-fenil]-Nmetil-piridino-4-carboxamida (Entrada 36 da tabela B) Etapa 1: 4-[1-[cloro(difluoro)metil]-1,2,2,2tetrafluoro-etil]-2-(difluorometoxi)anilina

[0327] A solution of 2-difluoromethoxyaniline (4.5 g) in a mixture of 2-methoxy-2-methylpropane (41 mL) and water (41 mL) was stirred at 20 °C. Sodium hydrosulfite (6.8 g), sodium bicarbonate (2.8 g), and tetrabutylammonium hydrogen sulfate (0.69 g) were added, followed by 1-chloro-1,1,2,3,3,3-hexafluoro-2-iodopropane (preparation described in Patent FR 1337264) (10.0 g). Gas release was observed during the first 4 hours. The mixture was stirred for 3 days, after which the phases were separated. The aqueous phase was extracted twice with 2-methoxy-2-methylpropane, and the combined organic phases were washed twice with aqueous hydrochloric acid. Petition 870190116135, dated 11 / 11 / 2019, pages 169 / 216 A 160 / 200 molar solution (100 mL) was used, followed by two washes with water (100 mL), then a saturated sodium chloride solution (100 mL). The organic phase was dried with sodium sulfate and the solvent removed under reduced pressure to yield 4-[1[chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-2(difluoromethoxy)aniline as an orange oil, which was used in the next step without further purification.

[0328] 1H NMR (400 MHz, CDCla, δ in ppm): 7.29 (m, 2H), 6.84 (d, J = 8.1 Hz, 1H), 6.49 (t, J = 73 Hz, 1H), 4.15 (sl, 2H). Step 2: 2-bromo-4-[1-[chloro(difluoro)methyl]1,2,2,2-tetrafluoroethyl]-6-(difluoromethoxy)aniline

[0329] To an orange solution of 4-[1[chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-2(difluoromethoxy)aniline (3.88 g) (preparation described in step 1) in dichloromethane (24 mL) was added in small pieces N-bromosuccinimide (2.41 g) under stirring at 20 °C. The reaction mixture turned dark brown. The reaction was complete after 1 hour (analysis by LC-MS). An aqueous solution of sodium hydroxide (100 mL, 1 mol / L) was added to the reaction mixture under stirring. After separation of the phases, the organic phase was washed with another 100 mL portion of 0.1 M sodium hydroxide. The combined aqueous phases were extracted twice with 100 mL of dichloromethane. The organic phases were combined and dried. Petition 870190116135, dated 11 / 11 / 2019, pages 170 / 216 161 / 200 with sodium sulfate and the solvent was removed under reduced pressure to give rise to 2-bromo-4-[1[chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6(difluoromethoxy)aniline as a brown oil which was used in the next step without further purification.

[0330] 1H NMR (400 MHz, CDCla, δ in ppm): 7.55 (s, 1H), 7.25 (s, 1H), 6.60 (t, J = 72.7 Hz, 1H), 4.60 (sl, 2H). Step 3: N-[2-bromo-4-[1-[chloro(difluoro)methyl] 1,2,2,2-tetrafluoro-ethyl]-6-(difluoromethoxy)phenyl]-2fluoro-3-nitro-benzamide

[0331] A solution of 2-bromo-4-[1[chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6(difluoromethoxy)aniline (4.38 g) (preparation described in step 2) in acetonitrile (25 mL) was treated with potassium iodide powder (0.172 g) followed by a solution of 2-fluoro-3-nitrobenzoyl chloride (2.53 g) in acetonitrile (20 mL). The resulting mixture was stirred under reflux for 20 hours. The reaction mixture was evaporated to dryness and the residue partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried with sodium sulfate and evaporated. The residue was purified by flash chromatography on silica gel eluting with a mixture of ethyl acetate and heptanes. Petition 870190116135, dated 11 / 11 / 2019, pages 171 / 216 162 / 200 N-[2-bromo-4-[1-[chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6-(difluoromethoxy)phenyl]-2-fluoro-3-nitrobenzamide was isolated as a solid that melts at 125-127 °C. Step 4: N-[2-bromo-4-[1-[chloro(difluoro)methyl]1,2,2,2-tetrafluoro-ethyl]-6-(difluoromethoxy)phenyl]-2methoxy-3-nitro-benzamide F

[0332] For a pale brown solution of N-[2-bromo-4-[1 [chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6-(difluoromethoxy)phenyl]-2-fluoro-3-nitrobenzamide (2.23 g) (preparation described in step 3) in methyl alcohol (35.6 mL) was added to potassium carbonate (1.10 g) and the resulting suspension was heated to 50 °C with stirring for 4 hours. The reaction was complete, and the reaction mixture was filtered. The filtrate was evaporated and the residue partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane and the organic solution dried with sodium sulfate and evaporated to give the desired compound as a brown oil. This was used in the next step without further purification.

[0333] 1H NMR (400 MHz, CDCla, δ in ppm): 9.09 (s, 1H), 8.37 (dd, J = 8.2 Hz, J = 2 Hz, 1H), 8.05 (dd, J = 8.2 Hz, J = 2 Hz, 1H), 7.82 (s, 1H), 7.52 (s, 1H), 7.43 (t, J = 8.2 Hz, 1H), 6.60 (t, J = 73.5 Hz, 1H), 4.14 (s, 3H). Stage 5 :3-amino-N- [2-bromo-4- [1[chloro(difluoro)methyl]-1,2,2,2-tetrafluoro-ethyl]-6Petition 870190116135, dated 11 / 11 / 2019, p. 172 / 216 163 / 200 (difluoromethoxy)phenyl]-2-methoxy-benzamide

[0334] A mixture of 2.306 g of N-[2-bromo-4-[1 [chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6-(difluoromethoxy)phenyl]-2-methoxy-3-nitrobenzamide (preparation described in step 4), iron powder (0.535 g), ethyl alcohol (31 mL), and water (6 mL) were mixed with 0.016 mL of concentrated aqueous hydrochloric acid. The pale green suspension was heated under reflux and rapidly turned brown. After stirring for two hours, the reaction was complete (analysis by LC-MS and TLC). The reaction mixture was filtered through a layer of celite, and the solid residue was washed with dichloromethane. The filtrate was evaporated and extracted with dichloromethane. The organic phase was dried with sodium sulfate and evaporated to yield the impure compound as a thick brown oil. This compound was used without further purification in the following step.

[0335] 1H NMR (400 MHz, CDCl3, δ in ppm): 9.42 (sl, 1H), 7.81 (s, 1H), 7.50 (m, 2H), 7.10 (t, J = 8.2 Hz, 1H), 6.97 (d, J = 8.2 Hz, 1H), 6.61 (t, J = 73.5 Hz, 1H), 3.98 (s, 3H), 3.95 (s, wide, 2H). Step 6: N-[2-bromo-4-[1-[chloro(difluoro)methyl]1,2,2,2-tetrafluoro-ethyl]-6-(difluoromethoxy)phenyl]-3(ethylamino)-2-methoxy-benzamide Petition 870190116135, dated 11 / 11 / 2019, pp. 173 / 216 164 / 200

[0336] To a solution of 1.411 g of 3-amino-N-[2-bromo-4[1-[chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6(difluoromethoxy)phenyl]-2-methoxybenzamide (preparation described in step 5) in 20 mL of methanol, 0.156 mL of acetic acid and 0.109 g of acetaldehyde were added, followed by 0.180 g of sodium cyanoborohydride. Gas release was observed. The reaction mixture was stirred at 20 °C for 17 hours. Then, the solvent was evaporated and the residue partitioned between dichloromethane and water. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried with sodium sulfate and evaporated. The impure product was subjected to flash chromatography on silica gel using a gradient from 10% ethyl acetate in cyclohexane to 20% ethyl acetate in cyclohexane. The desired product was isolated as a colorless solid with a melting point of 121–123 °C. Step 7: N-[3-[[2-bromo-6-(difluoromethoxy)-4[1,2,2,2-tetrafluoro-1(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenyl]-N-methyl-pyridine-4-carboxamide (Table B Entry 36) Petition 870190116135, dated 11 / 11 / 2019, pp. 174 / 216 165 / 200

[0337] To a colorless solution of 0.300 g of N-[2-bromo-4[1-[chloro(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6(difluoromethoxy)phenyl]-3-(ethylamino)-2-methoxybenzamide (preparation described in step 6) in 5.0 mL of tetrahydrofuran, 138 mg of isonicotinoyl chloride hydrochloride was added. The suspension was heated to 70 °C for 1 hour. The reaction was complete, as shown by LC-MS and TLC analyses. The reaction mixture was concentrated under reduced pressure and the extracted residue dissolved in dichloromethane. The organic phase was washed with saturated aqueous sodium bicarbonate. The aqueous phase was extracted again twice with dichloromethane. The organic phases were combined and dried with sodium sulfate and evaporated. The impure product was chromatographed on silica gel eluting with a mixture of 50% ethyl acetate and 50% cyclohexane.After solvent removal, N-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxyphenyl]-N-methylpyridine-4-carboxamide was obtained as a white powder with a melting range of 112-161 °C.

[0338] 1H NMR (400 MHz, CDCla, δ in ppm): 8.50 (s, broad, 2H), 8.02 (t, 1H), 7.83 (d, 1H), 7.78 (s, 1H), 7.49 (s, 1H), 7.43 (t, 1H), 7.28 (t, 1H), 7.18 (s, wide, 2H),6.55 (t, 1H), 4.00 (m, wide, 2H), 1.28 (t, wide, 3H). Example P5: N-[3-[[2-bromo-6-chloro-4-[1-(difluoromethyl)-1,2,2,2-tetrafluoroethyl]phenyl]carbamoyl]2-methoxyphenyl]-N-ethylpyridine-4-carboxamide (Entry 51 of Table B) Petition 870190116135, dated 11 / 11 / 2019, pp. 175 / 216 166 / 200 FF Cl

[0339] A solution of N-[3-[[2-bromo-4-[ 1[bromo(difluoro)methyl]-1,2,2,2-tetrafluoroethyl]-6-chlorophenyl]carbamoyl]-2-methoxyphenyl]-N-ethylpyridine-4-carboxamide (115 mg, 0.16 mmol, prepared analogously to the methods described above, entry 2, table B) dissolved in toluene (3 mL) was degassed with nitrogen, and then treated with tris(trimethylsilyl)silane (61 mg, 0.2404 mmol) and azo-bis(isobutyronitrile, AIBN) (61 mg, 0.016 mmol). The reaction was stirred at room temperature for 23 h, after which an LCMS showed that the reaction was complete. The reaction mixture was inactivated with 5 mL of water and extracted with 3 x 10 mL of ethyl acetate. The combined organic phases were washed with 10 mL of HCl solution (2 mol) and then with 20 mL of NaCl solution, dried with Na2SO4, filtered, and concentrated in vacuo. The impure product was purified by reverse-phase chromatography to give the product described above as a yellow resin.LCMS: (OA_Standard) : 638, 640, 642 (M + H), retention time. 1.03min 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.44 (t, J=7.15 Hz, 3H); 3.73 (m, 1H); 3.96 (s, 3H); 4.26 (m, 1 H); 5.99 - 6.41 (m, 1 H); 7.25 (1, 1H); 7.32 (d, J=5.50 Hz, H); 7.51 (d, J=6.97 Hz, 1 H); 7.62 - 7.70 (m, 1 H); 7.78 (s, 1 H); 7.96 - 8.11 (m, 1 H) 8.49 (sl, 2 H) 8.68 (sl, 1 H). Petition 870190116135, dated 11 / 11 / 2019, pp. 176 / 216 167 / 200 LC-MS method: ZCQ13 Waters ZQ Mass Spectrometer (Simple Quadrupole Mass Spectrometer) Instrument Parameters: Ionization method: Electrospraying. Polarity: positive and negative ions. Capillary: 3.00 kV. Cone: 30 V. Extractor: 2.00 V Source Temperature: 150 °C Desolvation Temperature: 350C Gas Flow in the Cone: 50 L / Hr Desolvation Gas Flow Rate: 400 L / Hr Mass Range: 100 to 900 Da Waters Acquity UPLC: Binary pump, heated column compartment and diode array detector. Solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 pm, 30 x 2.1 mm, Temp: 60 °C Wavelength range of DAD (nm): 210 to 500 Solvent Gradient: A = H2O + 5% MeOH + 0.05% HCOOH B= Acetonitrile + 0.05% HCOOH Flow Time A% B% (mL / min) Petition 870190116135, dated 11 / 11 / 2019, pp. 177 / 216 168 / 200 0.00 90 10 0.85 1.20 0 100.0 0.85 1.50 0 100.0 0.85 LC-MS Method: Waters ZDQ13 Mass Spectrometer (Single quadrupole mass spectrometer) Instrument Parameters: Ionization method: Electrospraying. Polarity: positive and negative ions. Capillary: 3.00 kV. Cone: 30 V. Extractor: 2.00 V Source Temperature: 150 °C Desolvation Temperature: 350C Gas Flow in the Cone: 50 L / Hr Desolvation Gas Flow Rate: 400 L / Hr Mass Range: 100 to 900 Da Waters Acquity UPLC: Binary pump, heated column compartment and diode array detector. Solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 pm, 30 x 2.1 mm, Temp: 60 °C Wavelength range of DAD (nm): 210 to 500 Solvent Gradient: A = H2O + 5% MeOH + 0.05% HCOOH Petition 870190116135, dated 11 / 11 / 2019, pp. 178 / 216 169 / 200 B = Acetonitrile + 0.05% HCOOH Time A% B% Flow (mL / min) 0.00 90 10 0.85 1.20 0 100.0 0.85 1.50 0 100.0 LC-MS Method: OA STANDARD 0.85 Waters ZQ Mass Spectrometer (Single Quadripole Mass Spectrometer) Instrument Parameters: Ionization method: Electrospraying. Polarity: positive and negative ions. Capillary: 3.00 kV. Cone: 30 V. Extractor: 2.00 V Source Temperature: 150 °C Desolvation Temperature: 350C Gas Flow in the Cone: 50 L / Hr Desolvation Gas Flow Rate: 400 L / Hr Mass Range: 100 to 900 Da Waters Acquity UPLC: Binary pump, heated column compartment and diode array detector. Solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 pm, 30 x 2.1 mm, Temp: 60 °C Wavelength range of DAD (nm): 210 to Petition 870190116135, dated 11 / 11 / 2019, pp. 179 / 216 170 / 200 500 Solvent Gradient: A = H2O + 5% MeOH + 0.05% HCOOH B= Acetonitrile + 0.05% HCOOH Temperature Flow A% B% o (mL / min) 0.00 90 10 0.85 1.20 0 100.0 0.85 1.50 0 100.0 0.85 The following compounds illustrate the invention: Table A. Radicals of formula (I) In which: Line X1 F CN 3-Pyridyl Petition 870190116135, dated 11 / 11 / 2019, pp. 180 / 216 171 / 200 11 OCH3 CN 3-Pyridyl 12 H CN 3-Pyridyl 13 FH 4-Cyanophenyl 14 OCH3 H 4-Cyanophenyl 15 HH 4-Cyanophenyl 16 F CN 4-Cyanophenyl 17 OCH3 CN 4-Cyanophenyl 18 H CN 4-Cyanophenyl 19 FH 4-Pyridyl-N-oxide 20 OCH3 H 4-Pyridyl-N-oxide 21 HH 4-Pyridyl-N-oxide 22 F CN 4-Pyridyl-N-oxide 23 OCH3 CN 4-Pyridyl-N-oxide 24 H CN 4-Pyridyl-N-oxide 25 FH 3-Pyridyl-N-oxide 26 OCH3 H 3-Pyridyl-N-oxide 27 HH 3-Pyridyl-N-oxide 28 F CN 3-Pyridyl-N-oxide 29 OCH3 CN 3-Pyridyl-N-oxide 30 H CN 3-Pyridyl-N-oxide 31 FH 4-Cyano-2-methylphenyl 32 OCH3 H 4-Cyano-2-methylphenyl 33 HH 4-Cyano-2-methylphenyl 34 F CN 4-Cyano-2-methylphenyl 35 OCH3 CN 4-Cyano-2-methylphenyl 36 H CN 4-Cyano-2-methylphenyl

[0340] Table 1 provides 36 compounds of formula (I) where X0 is H, Y1 is Cl, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36. Petition 870190116135, dated 11 / 11 / 2019, pp. 181 / 216 172 / 200

[0341] Table 2 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Cl, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0342] Table 3 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Cl, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0343] Table 4 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Br, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0344] Table 5 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Br, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0345] Table 6 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Br, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0346] Table 7 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Me, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0347] Table 8 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Me, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0348] Table 9 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Me, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0349] Table 10 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Et, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0350] Table 11 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36. Petition 870190116135, dated 11 / 11 / 2019, pages 182 / 216 173 / 200

[0351] Table 12 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Et, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0352] Table 13 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0353] Table 14 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0354] Table 15 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Cl, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0355] Table 16 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Br, Y2 is Br, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0356] Table 17 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Br, Y2 is Br, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0357] Table 18 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Br, Y2 is Br, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0358] Table 19 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Et, Y2 is Br, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0359] Table 20 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Br, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0360] Table 21 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Et, Y2 is Br, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36. Petition 870190116135, dated 11 / 11 / 2019, pages 183 / 216 174 / 200

[0361] Table 22 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Br, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0362] Table 23 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Br, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0363] Table 24 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Br, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-30 rows 136.

[0364] Table 25 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Br, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0365] Table 26 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Br, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0366] Table 27 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Br, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0367] Table 28 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Me, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0368] Table 29 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Me, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0369] Table 30 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Me, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0370] Table 31 provides 36 compounds of formula (I) where X0 is H, Y1 is Et, Y2 is Me, R2 is H, and X1, X2 and Q are Petition 870190116135, dated 11 / 11 / 2019, pp. 184 / 216 175 / 200 as defined in Table A, rows 1-36.

[0371] Table 32 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0372] Table 33 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Et, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0373] Table 34 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0374] Table 35 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0375] Table 36 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Me, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0376] Table 37 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Et, Y2 is Et, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0377] Table 38 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Et, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0378] Table 39 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Et, Y2 is Et, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0379] Table 40 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Et, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0380] Table 41 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Et, R2 is H, and X1, X2 and Q Petition 870190116135, dated 11 / 11 / 2019, pages 185 / 216 176 / 200 are as defined in Table A, rows 1-36.

[0381] Table 42 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Et, R2 is H, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0382] Table 43 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Cl, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0383] Table 44 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Cl, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0384] Table 45 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Cl, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0385] Table 46 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Br, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0386] Table 47 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Br, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0387] Table 48 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Br, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0388] Table 49 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Me, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0389] Table 50 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Me, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0390] Table 51 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Me, Y2 is Cl, R2 is Me, and X1, X2 and Q are Petition 870190116135, dated 11 / 11 / 2019, pages 186 / 216 177 / 200 as defined in Table A, rows 1-36.

[0391] Table 52 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Et, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0392] Table 53 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0393] Table 54 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Et, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0394] Table 55 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0395] Table 56 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0396] Table 57 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Cl, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0397] Table 58 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Br, Y2 is Br, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0398] Table 59 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Br, Y2 is Br, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0399] Table 60 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Br, Y2 is Br, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0400] Table 61 provides 36 compounds of formula (I) where X0 is H, Y1 is Et, Y2 is Br, R2 is Me, and X1, X2 and Q are Petition 870190116135, dated 11 / 11 / 2019, pages 187 / 216 178 / 200 as defined in Table A, rows 1-36.

[0401] Table 62 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Br, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0402] Table 63 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Et, Y2 is Br, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0403] Table 64 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Br, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0404] Table 65 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Br, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0405] Table 66 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Br, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0406] Table 67 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Br, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0407] Table 68 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Br, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0408] Table 69 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Br, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0409] Table 70 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Me, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0410] Table 71 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Me, Y2 is Me, R2 is Me, and X1, X2 and Q are Petition 870190116135, dated 11 / 11 / 2019, pages 188 / 216 179 / 200 as defined in Table A, rows 1-36.

[0411] Table 72 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Me, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0412] Table 73 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Et, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0413] Table 74 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0414] Table 75 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Et, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0415] Table 76 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0416] Table 77 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0417] Table 78 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Me, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0418] Table 79 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Et, Y2 is Et, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0419] Table 80 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Et, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0420] Table 81 provides 36 compounds of formula (I) where X0 is Br, Y1 is Et, Y2 is Et, R2 is Me, and X1, X2 and Q are Petition 870190116135, dated 11 / 11 / 2019, pages 189 / 216 180 / 200 as defined in Table A, rows 1-36.

[0421] Table 82 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Et, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0422] Table 83 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Et, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0423] Table 84 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Et, R2 is Me, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0424] Table 85 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Cl, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0425] Table 86 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Cl, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0426] Table 87 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Cl, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0427] Table 88 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Br, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0428] Table 89 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Br, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0429] Table 90 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Br, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0430] Table 91 provides 36 compounds of formula (I) where X0 is H, Y1 is Me, Y2 is Cl, R2 is Et, and X1, X2 and Q are Petition 870190116135, dated 11 / 11 / 2019, pages 190 / 216 181 / 200 as defined in Table A, rows 1-36.

[0431] Table 92 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Me, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0432] Table 93 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Me, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0433] Table 94 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Et, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0434] Table 95 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0435] Table 96 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Et, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0436] Table 97 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0437] Table 98 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0438] Table 99 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Cl, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0439] Table 100 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Br, Y2 is Br, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0440] Table 101 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Br, Y2 is Br, R2 is Et, and X1, X2 and Q are Petition 870190116135, dated 11 / 11 / 2019, pages 191 / 216 182 / 200 as defined in Table A, rows 1-36.

[0441] Table 102 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Br, Y2 is Br, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0442] Table 103 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Et, Y2 is Br, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0443] Table 104 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Br, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0444] Table 105 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Et, Y2 is Br, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0445] Table 106 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Br, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0446] Table 107 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Br, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0447] Table 108 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Br, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0448] Table 109 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Br, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0449] Table 110 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Br, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0450] Table 111 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Br, Y2 is Me, R2 is Et, and X1, X2 and Q are Petition 870190116135, dated 11 / 11 / 2019, pages 192 / 216 183 / 200 as defined in Table A, rows 1-36.

[0451] Table 112 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Me, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0452] Table 113 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Me, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0453] Table 114 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Me, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0454] Table 115 provides 36 compounds of formula (I) wherein X0 is H, Y1 is Et, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0455] Table 116 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is Et, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0456] Table 117 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is Et, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0457] Table 118 provides 36 compounds of formula (I) wherein X0 is H, Y1 is OCHF2, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0458] Table 119 provides 36 compounds of formula (I) wherein X0 is Cl, Y1 is OCHF2, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0459] Table 120 provides 36 compounds of formula (I) wherein X0 is Br, Y1 is OCHF2, Y2 is Me, R2 is Et, and X1, X2 and Q are as defined in Table A, rows 1-36.

[0460] Table 121 provides 36 compounds of formula (I) where X0 is H, Y1 is Et, Y2 is Et, R2 is Et, and X1, X2 and Q are Petition 870190116135, dated 11 / 11 / 2019, pages 193 / 216 184 / 200 as defined in Table A, rows 1-36.

[0461] Table 122 provides 36 compounds of formula (I) wherein XO is Cl, Y1 is Et, Y2 is Et, R2 is Et, and XI, X2 and Q are as defined in Table A, rows 1-36.

[0462] Table 123 provides 36 compounds of formula (I) wherein XO is Br, Y1 is Et, Y2 is Et, R2 is Et, and XI, X2 and Q are as defined in Table A, rows 1-36.

[0463] Table 124 provides 36 compounds of formula (I) wherein XO is H, Y1 is OCHF2, Y2 is Et, R2 is Et, and XI, X2 and Q are as defined in Table A, rows 1-36.

[0464] Table 125 provides 36 compounds of formula (I) wherein XO is Cl, Y1 is OCHF2, Y2 is Et, R2 is Et, and XI, X2 and Q are as defined in Table A, rows 1-36.

[0465] Table 126 provides 36 compounds of formula (I) wherein XO is Br, Y1 is OCHF2, Y2 is Et, R2 is Et, and XI, X2 and Q are as defined in Table A, rows 1-36. Table B: Properties of the Prepared Compounds Input STRUCTURE TR (min ) [M+H] (measure) Method PF °C 1 \ ιΆ' °' CX II 1 n F AÇ^^Br f \-FFF 1.20 740, 742, 744 ZDQ13 Petition 870190116135, dated 11 / 11 / 2019, pages 194 / 216 185 / 200 Input STRUCTURE TR (min ) [M+H] (measurement) Method PE °C 2 F BrA / NH °x Br FAF ff 1, 10 688, 690, 692 ZDQ13 4 jQl0 a hn r 0 FAF HN. THE. f M 0 ϊιx F τΌ ff 1, 07 708, 710, 712 ZCQ13 5 hn ° AF HN. A. cp ífj 0 ΥΊ x N F- / F<F 1, 15 732, 734, 736 ZCQ13 6 O > =< o OJ 1.00 724, 726, 728 ZCQ13 Petition 870190116135, dated 11 / 11 / 2019, pages 195 / 216 186 / 200 Entrada ESTRUTURA TR (min ) [M+H] (medida) Método PF °C 7 TI W \ V / \ ° ” z-^ x \ ’O / —Z ' )=° 1, 10 736, 738, 740 162 164 8 F f F k X 1 l| F —^Br F \-F Br F 1, 17 760, 762, 764 ZCQ13 9 f ΒΓ,Λγ™ °s X F \-F Á F F f f 1, 11 748, 750, 752 ZCQ13 10 f βγτΑτνη °x x x\ X 1 II xn FF >F 1 f^F F F 1, 18 772, 774, 776 ZCQ13 11 HN O^F F ΗΝγ\ fk / Br^ACCI f-Z F f f 1,06 6 64, 666, 668 ZCQ13 118 157 Petição 870190116135, de 11 / 11 / 2019, pág. 196 / 216 187 / 200 Entrada ESTRUTURA TR (min ) [M+H] (medida) Método PE °C 12 XXX ojO F NH F Y T ° u 1,08 6 64, 666, 668 ZCQ13 140 151 13 XXo a HN γ γ 0 F F HN. d. f jQ) 0 XI x N f-ZF 1, 15 688, 690, 692 ZCQ13 116 151 14 jCLo i HN 1 ( 0 f fj 0 Tji χ Br 7x F -Z F F^F 172 174 15 F / F F / NX fj-α T í| Ί FX Ίτ Η ° 0 1 — F F A^Js^NH ; - U 1, 10 676, 678, 680 ZCQ13 90 170 16 XXo A HN 0 F c F ju 0 Xlx N F-A f f^f 2Η RMN (400 MHz, CDCls, δ em ppm): 8,90 (s, 1H) , 8,67 (d, J = 8, 1 97 172 Petition 870190116135, dated 11 / 11 / 2019, p. 197 / 216 188 / 200 Input STRUCTURE TR (min ) [M+H] (measured) PE Method °C Hz, 1H), 8.46 (s, 1H), 8.03 (d, J = 9 Hz, 2H), 7.90-7.80 (m, 4H), 7.52 (s, J, 1 =3) 1H), 6, 63 (t, J = 73 Hz, 1H), 4.04 (s, 3H) . 17 XX0, hn 1 Γ l XF HN . FLUENT. c F fj 0 Yjx F - / f F f 1, 10 626, 628, 630 ZCQ13 108 190 18 Ar o λ FF Sp NH F 171 173 Petition 870190116135, dated 11 / 11 / 2019, p. 198 / 216 189 / 200 Input STRUCTURE TR (min ) [M+H] (measurement) PE Method °C 19 jCUo . hn 1 jQj 0 Yjl X Br ClN F - / F ff 1, 17 650, 652, 654 ZCQ13 123 202 20 \_za- o / pz « cP \=^ o Q 1, 12 613, 64 2 ZJC, 60 FJ Cl o JÔ FF P-. / XXF γ nh ο γ UQr 1, 12 638, 640, 642 ZCQ13 87 168 22 ΗΝ^Ρψ5 f Xjj 0 Xjlx NF 6 6 1, / FF^f ZCQ13 110 170 23 HN 0^F ^s. F HN . FLUENT. . f lí^J 0 Ϊ1Χ O'N^ Br^^SCci FZ F f F 230 232 Petition 870190116135, dated 11 / 11 / 2019, p. 199 / 216 190 / 200 Entrada ESTRUTURA TR (min ) [M+H] (medida) Método PE °C 24 jÇUo A HN er yx OF tho f hn . xL r FN O YF / U BrJWa F- / FF^F 197 201 25 iXo 1 hn ΙΓ i 0 F λ. A os.hn. A. F (Cj 0 il xf Vf ff 1, 02 692, 694, 696 ZCQ13 177 186 26 jQLo a HN γ γΧ OF Of x^A O. HN. A. - r UB,V / a fV F f^f 1, 02 692, 694, 696 ZCQ13 177 186 26 27 xCL?0 / hn γ p AF hn. c F Cj 0 ilx FZ 1, 02 644, 646 ÁXo . HN qx p Of X3^ At F HN . c FN Ο FFU „ FAF ff Petition 870190116135, de 11 / 11 / 2019, pág. 200 / 216 191 / 200 Entrada ESTRUTURA TR (min ) [M+H] (medida) Método PE °C 29 o Y Φ * 7^ o 1, 04 654, 656, 658 ZCQ13 158 167 30 hn IG C 1 OJ O^HN, Y rr U BrV / c. f-ZF FF 229 231 31 z Λ ° ' / Z—' \ I ^-2 £ O u u_ 1, 17 716, 718, 720 ZCQ13 80 150 32 «“'τΌ' fVji F Cl Xy-NH O^ \ XL li NF^V^tx^o F \-F 1 FFFF 1,19 728, 730, 732 ZCQ13 80 159 33 f F fXNHI F \ X [1 1 N FF Cl F 1.19 678, 680, 682 ZCQ13 99 173 Petition 870190116135, dated 11 / 11 / 2019, pages 201 / 216 192 / 200 Input STRUCTURE TR (min ) [M+H] (measurement) Method PE °C 34 F Cl °X \ fXXJL F Af 1 f F 1,22 690, 692, 694 ZCQ13 106 152 35 F FF \ X / NFF Af Cl F 1, 10 692, 694, 696 ZCQ13 106 154 36 F Cl °\ XX / NFF AF 1 FFFF 1, 12 704, 706, 708 ZCQ13 120 171 38 o^jÇL F Cl ΑγΝΗ °xk F AF 1 FF 1, 14 6 6 6, 668, 670 ZCQ13 90 155 Petition 870190116135, dated 11 / 11 / 2019, pages 202 / 216 193 / 200 Input STRUCTURE TR (min ) [M+H] (measurement) Method PE °C 39 f 1, 11 692, 694, 696 ZCQ13 100 162 40 F / / N\ f / / -<=> ' Γη F / fT° ° ° f F Br H 1 1, 13 704, 706, 708 ZCQ13 110 164 41 •n A ú 1, 14 652, 654, 656 ZDQ13 96 144 42 O / =\ / °“O o=( --» ZX u. 1,16 6 6 6, 668, 670 ZDQ13 80 137 43 •n - / \ ° ? Z-^1\z—Z' )=° 0 o 1 1.03 708, 710, 712 ZCQ13 115 203 Petition 870190116135, dated 11 / 11 / 2019, pages 203 / 216 194 / 200 Input TR STRUCTURE (min ) [M+H] (measurement) Method PE °C 44 v rVH °' ^“'o- f \-F 1 FF ff 1, 04 720, 722, 724 ZCQ13 109 228 45 •n - AJ / \ ° x \ / —z / \=OOO i 1.05 670, 672, 674 ZCQ13 118 209 46 v rrNH °x ^N'o· FF AF 1 ff 1, 04 + 1.06 682, 684, 686 ZCQ13 112 220 47 n Q 'yU' / \ ° ? z-4 I \ y—Z / \=O °'O 1.03 708, 710, 712 ZCQ13 98 211 48 o^Çl F ri NH °κ < Ί \ Cl < N ,ΟΛ i- F Af Á FF f = 1, 04 720, 722, 724 ZCQ13 104 202 Petition 870190116135, dated 11 / 11 / 2019, pages 204 / 216 195 / 200 Input STRUCTURE TR (min) [M+H] (measurement) Method PE °C 49 X JL1C a- F*y^Br o F Af Cl F 1.05 670, 672, 674 ZCQ13 118 230 50 \ Cl / vNH °x < FUÀ ó- f Af IFF 1.06 682, 684, 686 ZCQ13 99 208 51 Cl 1.03 638, 640, 642 OA_PADRÃO Biological examples

[0466] These Examples illustrate the insecticidal and acaricidal properties of the compounds of formula (I). The tests were carried out as follows:

[0467] Bemisia tabaci (Cotton whitefly): Cotton leaf discs are placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs are infested with adult whiteflies. After an incubation period of 6 DAI, the samples are checked for mortality. Petition 870190116135, dated 11 / 11 / 2019, pages 205 / 216 196 / 200 The following compound provided at least 80% control of Bemisia tabaci: 2, 3, 4, 5, 6, 7. Diabrotica balteata (Corn rootworm):

[0468] A 24-well microtiter plate (MTP) with an artificial feeding regime was treated with test solutions at an application rate of 200 ppm (concentration in the well 18 ppm) by pipetting. After drying, the MTPs were infested with L2 larvae (6-10 per well). After a 5-day incubation period, the samples were checked for larval mortality. The following compound gave at least 80% control of Diabrotica balteata: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51. Frankliniella occidentalis (Western Flower Thrips):

[0469] Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with a mixed-age Frankliniella population. After an incubation period of 7 DAT, the samples were checked for mortality.

[0470] The following compounds gave control of at least 80% of Frankliniella occidentalis: 2, 3, 4, 5, 6, 7. Heliothis virescens (Tobacco caterpillar):

[0471] Eggs (0-24 h old) were placed in 24-well microtiter plates with an artificial feeding regime and treated with test solutions at a rate of Petition 870190116135, dated 11 / 11 / 2019, pages 206 / 216 197 / 200 application of 200 ppm (concentration in the well 18 ppm) by pipetting. After an incubation period of 4 days, the samples were checked for larval mortality.

[0472] The following compounds gave control of at least 80% of Heliothis virescens: 1, 2, 3, 4. Myzus persicae (Green peach aphid):

[0473] Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with a population of mixed-age aphids. After an incubation period of 6 DAT, the samples were checked for mortality.

[0474] The following compounds gave control of at least 80% of Myzus persicae: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51. Myzus persicae (Green peach aphid):

[0475] Pea seedling roots, infested with a mixed-age aphid population, are placed directly into test solutions at an application rate of 24 ppm. Six days after introduction, samples are checked for mortality.

[0476] The following compounds gave control of at least 80% of Myzus persicae: 14, 43, 44, 45, 46. Myzus persicae (Green peach aphid):

[0477] The test compounds were applied via pipette to 24-well plates and mixed with sucrose solution. Application rate: 12.5 ppm. The plates were Petition 870190116135, dated 11 / 11 / 2019, pages 207 / 216 198 / 200 plates were sealed with a stretched Parafilm. A plastic stencil with 24 holes was placed on the plate, and infested pea seedlings were placed directly on the Parafilm. The infested plate was sealed with gel blotting paper and another plastic stencil, then turned upside down. Five days after infestation, the samples were checked for mortality.

[0478] The following compounds gave control of at least 80% of Myzus persicae: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51. Plutella xylostella (Cruciferous moth):

[0479] A 24-well microtiter plate (MTP) was treated with an artificial feeding regime using test solutions at an application rate of 200 ppm (concentration in the well 18 ppm) by pipetting. After drying, the MTPs were infested with L2 larvae (7-12 per well). After a 6-day incubation period, the samples were checked for larval mortality and growth regulation. The following compounds resulted in at least 80% mortality of Plutella xylostella: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50. Spodoptera littoralis (Egyptian cotton leafworm):

[0480] Cotton leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate. Petition 870190116135, dated 11 / 11 / 2019, pages 208 / 216 199 / 200 of 200 ppm. After drying, the leaf discs were infested with 5 L1 larvae. The samples were evaluated for mortality 3 days after treatment (DAT).

[0481] The following compounds gave a mortality rate of at least 80% of Spodoptera littoralis: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51.

[0482] Spodoptera littoralis (Egyptian cotton bollworm): Test compounds were applied via pipette to 24-well plates and mixed with agar. Application rate: 12.5 ppm. Lettuce seeds were placed in the agar, and the multi-well plate was sealed with another plate also containing agar. After 7 days, the roots absorbed the compound, and the lettuce grew onto the lid plate. Lettuce leaves were then cut onto the lid plate. Spodoptera eggs were pipetted with a plastic stencil onto a wet gel staining paper, and the plate was sealed with the same. Samples were checked for mortality 6 days after infestation.

[0483] The following compounds gave control of at least 80% of Spodoptera littoralis: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 21, 23, 24, 25, 26, 31, 32, 35, 36, 39, 40, 41, 43, 44, 47, 48, 50. Tetranychus urticae (Two-spotted spider mite):

[0484] Bean leaf discs on agar in 24-well microtiter plates were sprayed with test solutions at an application rate of 200 ppm. After drying, Petition 870190116135, dated 11 / 11 / 2019, pages 209 / 216 200 / 200 leaf discs are infested with mixed-age mite populations. Eight days later, the discs were checked for mortality.

[0485] The following compounds gave a mortality rate of at least 80% of Tetranychus urticae: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51. Thrips tabaci (Onion thrips):

[0486] Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with a population of mixed-age aphids. After a 7-day incubation period, the samples were checked for mortality.

[0487] The following compounds gave control of at least 80% of Thrips tabaci: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51.

Claims

1. Compound of formula (I) (I) characterized in that Xo is hydrogen; X1 is hydrogen; X2 is a cyano group; Y1 and Y2 are independently chlorine, bromine, iodine, C1-C4 alkyl groups, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R1 and R2 are independently hydrogen, C1-C8 alkyl groups, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, hydroxyl, C1-C8 alkyloxy, and C1-C4 aminocarbonylalkylene; G1 and G2 are both oxygen; Q is a group selected from Q1, Q2, Q3, Q4 and Q5, where Q1 is a group of formula (IIa) (W1)n1 Qi = I—C y (IIa) where the substituents W1 are independently selected from hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy groups, and n1 is 0, 1 or 2; Petition 870210086464, dated 20 / 09 / 2021, p.15 / 18 2 / 4 Q2 is a group of formula (IIb) Q2 = (IIb) where W2 is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy groups; Q3 is a group of formula (IIc) Q3 = (IIc) where W3 is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy groups; Q4 is a group of formula (IId) w4 i_ / A Q4 = K / (IId) where W4 is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy groups; and Q5 is a group of formula (IIe) / W5Q5 = (IIe) where W5 is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy groups; Petition 870210086464, dated 20 / 09 / 2021, page 16 / 18 3 / 4 or an agrochemically acceptable salt or N-oxides thereof.

2. Compound of formula (I), according to claim 1, characterized in that Y1 and Y2 are selected from Cl, Br, I, methyl, ethyl, methoxy, difluoromethoxy and trifluoromethoxy, R1 is selected from hydrogen and C1-C2 alkyl groups; R2 is selected from hydrogen and C1-C2 alkyl groups; Xi is hydrogen; X2 is a cyano group; and G1 and G2 are both oxygen.

3. Compound of formula (III) (III) characterized in that Xo, Yi, Y2, Xi, X2, R1, and R2 are as defined in claim 1 or 2.

4. Method for controlling insects, mites, nematodes or molluscs characterized by comprising the application to a pest, a locus of a pest, or a plant susceptible to attack by a pest, of an effective quantity in terms of insecticide, acaricide, nematicide or molluscicide of a compound of formula (I), as defined in claim 1 or 2, with the exception of a therapeutic and / or treatment method applied to the human or animal body. Petition 870210086464, dated 20 / 09 / 2021, pp. 17 / 18 4 / 4 5. Insecticidal, acaricidal, nematicidal or molluscicidal composition characterized by comprising an effective amount in terms of insecticidal, acaricidal, nematicidal or molluscicidal activity of a compound of formula (I), as defined in claim 1 or 2, together with an agrochemically acceptable diluent or carrier.

6. Composition according to claim 5, characterized by further comprising one or more insecticidal, acaricidal, nematicidal or molluscicidal compounds.

7. A method for protecting useful plants from insects, mites, nematodes or molluscs, characterized by comprising the application to said plants, to their locus, or to plant propagation material thereof, of an amount effective in terms of insecticide, acaricide, nematicide or molluscicide of a compound of formula I as defined in claim 1 or 2.