Method for controlling or preventing plants from being infected by plant pathogenic microorganism Corynespora polytomata

Abstract

The present invention relates to a method for controlling or preventing plants from being infected by the plant pathogenic microorganism Coryneformis, which comprises applying a fungicidally effective amount of a compound as defined in claim 1 to the plant pathogen, the site of the plant pathogen, or a plant susceptible to attack by the plant pathogen, or its propagation material.

Description

Technical Field

[0001] The present invention relates to a method for controlling or preventing plants from being infected by the plant pathogenic microorganism Corynespora cassiicola. Background Art

[0002] Coryneformis infects more than 530 species of plants from 53 families (Dixon, LJ, et al., 2009, Phytopathology 99 (9) 1015-27). Coryneformis is most common in tropical and subtropical areas. Also, it has been isolated from nematodes and human skin. Coryneformis is known to be a pathogen of many crop plants (e.g., beans, cowpeas, cucumbers, papayas, soybeans, sweet potatoes, and tomatoes). The disease caused by Coryneformis is called target leaf spot or target spot on several plants (e.g., tomatoes).

[0003] The plant pathogen Coryneformis multifilaments has developed resistance to many current commercial solutions, which limits their effectiveness, and, although the development of new classes of agricultural chemical fungicides is ongoing, many of these new chemical classes are limited in their fungicidal spectrum and only control certain specific plant pathogens. That is, when a new chemical class is shown to control certain specific plant pathogens on certain specific crops, it is not expected that the same chemical class will prove useful for controlling the plant pathogen Coryneformis multifilaments on, for example, soybeans.

[0004] Therefore, there is a need to develop new methods for controlling or preventing infection by the plant pathogen Corynespora multilocus. DETAILED DESCRIPTION

[0005] In WO 2017 / 153380 and WO 2018 / 172133, carboxamide quinoline compounds and methods for their preparation are disclosed. It has now been surprisingly found that specific carboxamide quinoline compounds disclosed in WO 2017 / 153380 and / or WO 2018 / 172133 are very effective in controlling or preventing plants from being infected by the plant pathogenic microorganism Coryneformis. Therefore, these very effective compounds provide farmers with an important new solution for controlling or preventing plants from being infected by the plant pathogenic microorganism Coryneformis.

[0006] Therefore, as in Example 1, a method for controlling or preventing plants from being infected by the plant pathogenic microorganism Coryneformis is provided, the method comprising applying a fungicidal effective amount of a compound to the plant pathogen, the site of the plant pathogen, or a plant susceptible to the plant pathogen, or its propagation material, the compound is selected from

[0007]

[0008]

[0009] or an enantiomer thereof.

[0010] Methods for preparing compounds as described in Example 1 are described in WO 2017 / 153380 and WO 2018 / 172133.

[0011] A more preferred method as described in Example 1 is given in the following examples.

[0012] As embodiment 2, there is provided a method as described in embodiment 1, wherein the compound is selected from

[0013]

[0014]

[0015]

[0016] As embodiment 3, there is provided a method as described in embodiment 1 or embodiment 2, wherein the compound is selected from

[0017]

[0018] As example 4, there is provided a method as described in example 1 or example 2, wherein the compound is selected from

[0019]

[0020] As example 5, there is provided a method as described in example 1 or example 2, wherein the compound is selected from

[0021]

[0022] As example 6, there is provided a method as described in example 1 or example 2, wherein the compound is selected from

[0023]

[0024] As example 7, there is provided a method as described in example 1 or example 2, wherein the compound is selected from

[0025]

[0026] As in embodiment 8, there is provided a method as in embodiment 1 or embodiment 2, wherein the compound is selected from

[0027]

[0028] The compounds described as example 1 represent racemic compounds, whereas the compounds disclosed in examples 2 to 8 disclose enantiomers ((R) or (S)) with a specific stereochemistry. How to resolve racemic mixtures (e.g. by chiral chromatography) is part of the common general knowledge of the person skilled in the art.

[0029] As embodiment 9, provided is the method of any one of embodiments 2 to 8, wherein the compound is the (R)-enantiomer.

[0030] As embodiment 10, provided is the method of any one of embodiments 2 to 8, wherein the compound is the (S)-enantiomer.

[0031] The racemic compound as described in Example 1 is a 1:1 mixture of (R) and (S) enantiomers.

[0032] The skilled person knows that, as in any one of the methods of Examples 1 to 8, the compound is usually applied as part of a pesticidal composition. Therefore, as in Example 11, a method for controlling or preventing a plant from being infected by a plant pathogenic microorganism, Coryspora multinomial, is provided, the method comprising applying a pesticidal composition to a plant pathogen, a site of the plant pathogen, or a plant susceptible to the attack of the plant pathogen, or its propagation material, the pesticidal composition comprising a compound as defined in any one of Examples 1-8 and one or more formulation adjuvants. As in Example 12, a method for controlling or preventing a plant from being infected by a plant pathogenic microorganism, Coryspora multinomial, is provided, the method comprising applying a pesticidal composition to a plant pathogen, a site of the plant pathogen, or a plant susceptible to the attack of the plant pathogen, or its propagation material, the pesticidal composition comprising an (R)-enantiomer of a compound as defined in any one of Examples 1 to 8 and one or more formulation adjuvants. As in Example 13, a method for controlling or preventing plants from being infected by the plant pathogenic microorganism Coryneformis is provided, the method comprising applying a pesticidal composition to the plant pathogen, the locus of the plant pathogen, or a plant susceptible to attack by the plant pathogen, or its propagation material, the pesticidal composition comprising the (S)-enantiomer of the compound defined in any one of Examples 1 to 8 and one or more formulation adjuvants. In the method as in Example 14, for the pesticidal composition comprising both the (R)-enantiomer of the compound defined in any one of Examples 1 to 8 and the (S)-enantiomer of the compound defined in any one of Examples 1 to 8, the ratio of the (R)-enantiomer to the (S)-enantiomer is preferably greater than 1:1. More preferably, the ratio of (R)-enantiomer to (S)-enantiomer is greater than 1.5:1, even more preferably greater than 2.5:1, especially greater than 4:1, advantageously greater than 9:1, desirably greater than 20:1, in particular greater than 35:1.

[0033] As embodiment 15, a method as described in any one of embodiments 1 to 14 is provided, wherein the method comprises the following steps

[0034] providing a composition comprising a compound as defined in any one of embodiments 1 to 14;

[0035] applying the composition to propagation material;

[0036] The propagation material is planted.

[0037] As embodiment 16, a method as described in any one of embodiments 1 to 14 is provided, wherein the method comprises the following steps

[0038] providing a composition comprising a compound as defined in any one of embodiments 1 to 14;

[0039] The composition is applied to a phytopathogen, the locus of the phytopathogen, or a plant susceptible to attack by the phytopathogen.

[0040] As embodiment 17, there is provided use of a compound as defined in any one of embodiments 1 to 14 for controlling or preventing plants from being infected by the plant pathogenic microorganism Corynespora multilocus.

[0041] As in embodiment 18, a method or use as described in any one of embodiments 1 to 17 is provided, wherein the plant is selected from beans, cowpeas, cucumbers, papayas, soybeans, sweet potatoes, tomatoes, cotton, eggplants, basil, thyme, rubber trees, papaya trees, azaleas and hydrangeas.

[0042] As embodiment 19, there is provided a method or use as described in any one of embodiments 1 to 17, wherein the plant is selected from beans, cowpeas, cucumbers, papayas, soybeans, sweet potatoes and tomatoes.

[0043] As embodiment 20, provided is the method or use of any one of embodiments 1 to 17, wherein the plant is soybean.

[0044] The preparation of compounds as defined in the method of any one of Examples 1 to 14 has been disclosed in WO 2017 / 153380 and WO 2018 / 172133, which are incorporated herein by reference.

[0045] The method and use as described in any one of Examples 1 to 20 are preferably used to control or prevent crops from being infected by plant pathogenic microorganisms that are resistant to other fungicides. "Resistant" to a particular fungicide is a fungus strain that is less sensitive to that fungicide, for example, compared to the expected sensitivity of the same fungus species. The expected sensitivity can be measured using, for example, a strain that has not been previously exposed to a fungicide.

[0046] According to the method or use as described in any one of embodiments 1 to 20, preferably applied to plant crops, their place or their propagation materials. Preferably applied to plant pathogens, the place of the plant pathogens, or plants susceptible to the plant pathogens, or their propagation materials. The application of the compound as defined in any one of embodiments 1 to 14 can be carried out according to any common application mode (e.g., leaf application, drench application, soil application, furrow irrigation application, etc.).

[0047] The compound as defined in any one of embodiments 1 to 14 is preferably used for pest control at a rate of 1 to 500 g / ha, preferably 50-300 g / ha.

[0048] The compounds as defined in any one of embodiments 1 to 14 are suitable for use on any plant, including those that have been genetically modified to be resistant to active ingredients such as herbicides, or those that have been genetically modified to produce biologically active compounds that control infestation by plant pests.

[0049] Typically, the compound as defined in any one of Examples 1 to 14 is used in the form of a composition (eg, a formulation) containing a carrier. The compounds and compositions thereof as defined in any one of Examples 1 to 14 can be used in different forms, such as aerosol sprays, capsule suspensions, concentrated cold mists, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, encapsulated granules, fine granules, flowable concentrates for seed treatment, gases (under pressure), gas-producing products, granules, concentrated hot mists, large granules, microgranules, oil-dispersible powders, oil suspensions, oil-soluble liquids, pastes, plant sticks, powders for dry seed treatment, seeds coated with pesticides, soluble concentrates, soluble powders, solutions for seed treatment, suspension concentrates (flowable concentrates), ultra-low volume (ulv) liquids, ultra-low volume (ulv) suspensions, water-dispersible granules or tablets, water-dispersible powders for slurry treatment, water-soluble granules or tablets, water-soluble powders for seed treatment and wettable powders.

[0050] The compositions of the present invention, including all of the above disclosed embodiments and preferred examples thereof, may be mixed with one or more additional pesticides, including additional fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form multi-component pesticides giving a broader spectrum of agricultural protection.

[0051] Examples of mixture compositions are as follows, and wherein the term "TX" represents a compound as defined in any one of Examples 1 to 8:

[0052] A compound selected from the group consisting of: petroleum + TX, 1,1-bis(4-chloro-phenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenylphenyl sulfone + TX, acetofenamide + TX, aldicarb + TX, sirox + TX, fruit manphos + TX, amine dephosphite + TX, ammonium dephosphite hydrogen oxalate + TX, amitraz + TX, cypermethrin + TX, arsenic trioxide + TX, azobenzene + TX, azophos + TX, benomyl + TX, benoxafos + TX, benzyl benzoate + TX, bixafen + TX, bromomethrin + TX, bromophenazine + TX X, bromophos + TX, bromopyralid + TX, buprofezin + TX, butanone + TX, butanone sulfone + TX, butyl pyridaben + TX, calcium polysulfide + TX, octachlorocamphene + TX, chlormethoxam + TX, trithion + TX, cypermethrin + TX, cypermethrin + TX, cypermethrin + TX, cypermethrin hydrochloride + TX, cypermethrin + TX, cypermethrin + TX, dimethoate + TX, ethyl cypermethrin + TX, cypermethrin (chloromebuform) + TX, cypermethrin + TX, propyl cypermethrin + TX, cypermethrin + TX, cypermethrin I + TX, cypermethrin II + TX, cypermethrin + TX, closantel + TX, coumaphos + TX, crotamiton + TX 、Batophos+TX、Thiophanate+TX、Fructofen+TX、DCPM+TX、DDT+TX、Tianlephos+TX、Tianlephos-O+TX、Tianlephos-S+TX、Demeton-methyl+TX、Demeton-O+TX、Demeton-O-methyl+TX、Demeton-S+TX、Demeton-S-methyl+TX、Demeton-S-methyl+TX、Demeton-S-methyl+TX、Demeton-S-methyl+TX、Bioflavonoid+TX、Dichlorvos+TX、Dicliphos+TX、Dicerin+TX、Mefluphos+TX、Dinex+TX、Dinex-diclexine+TX、Dinex-4+TX、 Dimethoate-6+TX, antrimide+TX, nitropentyl+TX, nitrobenzene+TX, nitrobenzene acaricide+TX, nitrobutyl+TX, dimethoate+TX, sulfodiphenyl+TX, disulfiram+TX, DNOC+TX, dofenapyn+TX, doramectin+TX, indole+TX, eprinomectin+TX, phosphosulfate+TX, ethiprox+TX, anti-mite+TX, fenbutatin+TX, fenthiocarb+TX, fenpyrad+TX, fenpyraclostrobin+TX, fenamipyraclostrobin+TX, fentrifanil+TX, fluazifop+TX, flufenoxuron+TX, diflunisal+TX, flufenicol+TX, FMC 1137+TX, flufenamic acid+TX, flufenamic acid hydrochloride+TX, formparanate+TX,γ-HCH+TX, fruit green +TX, benzyl acarboxylate +TX, hexadecyl cyclopropane carboxylate +TX, isocarbophos +TX, jasmonate I +TX, jasmonate II +TX, iodine +TX, lindane +TX, propanil +TX, cypermethrin +TX, dithiophos +TX, methylthiophene +TX, cypermethrin +TX, methyl bromide +TX, cypermethrin +TX, chlorpyrifos +TX, milbemycin +TX, propylamine +TX, monocrotophos +TX, maoguo +TX, moxidectin +TX, naled +TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazine-3-one +TX, fluazifop +TX, nikkomycin +TX, Pencyprodinil + TX, Pencyprodinil 1:1 zinc chloride complex + TX, Oxydemeton-methyl + TX, Isopropylphos + TX, Sulfonate + TX, pp'-DDT + TX, Parathion + TX, Permethrin + TX, Fenthion + TX, Phosalone + TX, Sulfonate + TX, Phosphamidon + TX, Polychloroterpenes + TX, Polynactins + TX, Proclorvin + TX, Fenthiazine + TX, Propoxur + TX, Ethiothiazophos + TX, Fenthiazine + TX, Pyrethrin I + TX, Pyrethrin II + TX, Pyrethrin + TX, Pyrithiophos + TX, Pyrithiophos + TX, Quinalphos + TX, Quinalphos (quintiofos) + TX, R-1492 + TX, glyphosate + TX, rotenone + TX, octamethrin + TX, clematin + TX, selamectin + TX, thion + TX, SSI-121 + TX, sulfilam + TX, sulfluramid + TX, sulfotep + TX, sulfur + TX, flumethoxam + TX, τ-fluvalinate + TX, TEPP + TX, tert-butylcarb + TX, tetrachlorocarbamide + TX, miticide + TX, thiafenox + TX, anthelmintic + TX, long-lasting anthelmintic + TX, methyl thiocarb + TX, miticide + TX, thuremycin + TX, fenthion + TX, benzyl thiocarb + TX, triazophos + TX, triazuron + TX, triazophos + TX, Chloropropoxyphos + TX, triactin + TX, aphidicide + TX, vaniliprole + TX, bethoxazin + TX, copper dioctanoate + TX, copper sulfate + TX, cybutryne + TX, dichloronaphthoquinone + TX, dichlorophen + TX, endoxan + TX, triphenyltin + TX, slaked lime + TX, mancozeb + TX, algaquinone + TX, quinone + TX, simazine + TX, triphenyltin acetate + TX, triphenyltin hydroxide + TX, yuxu phosphorus + TX, piperazine + TX, thiophanate + TX, chloralose + TX, fenthion + TX, pyridine-4-amine + TX, strychnine + TX, 1-hydroxy-1H-pyridine-2-thione + TX,4-(Quinoxalin-2-ylamino)benzenesulfonamide+TX, 8-Hydroxyquinoline sulfate+TX, bronopol+TX, copper hydroxide+TX, cresol+TX, dipyrithione+TX, dodesine+TX, sodium sulfadiazine+TX, formaldehyde+TX, mercurygafen+TX, kasugamycin+TX, kasugamycin hydrochloride hydrate+TX, nickel di(dimethyldithiocarbamate)+TX, trichloromethylpyridine+TX, octhilthione+TX, oxolinic acid+TX, oxytetracycline+TX, potassium hydroxyquinoline sulfate+TX, thiabendazole+TX, streptomycin+TX, streptomycin sesquisulfate+TX, chlorothiazide+TX, thimerosal+TX, cotton brown banded moth GV+TX, Agrobacterium radiobacterium+TX, Amblyseius spp.+TX, Spodoptera exigua NPV+TX, Anagrus spp. atomus+TX, short-spurred aphid wasp+TX, Aphidius colemani+TX, Aphidoletes aphidimyza+TX, Spodoptera lucerne NPV+TX, Bacillus sphaericus Neide+TX, Beauveria brongniartii+TX, Chrysoperla carnea+TX, Cryptolaemus montrouzieri+TX, Codling moth GV+TX, Dacnusasibirica+TX, Diglyphus isaea+TX, Encarsia formosa+TX, Eretmocerus eremicus)+TX, Heterorhabditis bacteriophora and H. megidis+TX, Hippodamia convergens+TX, Leptomastix dactylopii+TX, Macrolophus caliginosus+TX, Cabbage armyworm NPV+TX, Metaphycus helvolus+TX, Metarhizium anisopliae var. acridum+TX, Metarhizium anisopliae var. anisopliae+TX, Neodiprion sertifer NPV and N. lecontei NPV+TX,+TX, Paecilomyces fumosorum +TX, Phytoseiulus persimilis +TX, Steinernema bibionis +TX, Steinernema carpocapsae +TX, Steinernema glaseri +TX, Steinernema riobrave +TX, Steinernema riobravis +TX, Steinernema capterisci +TX, Steinernema spp. +TX, Trichogramma +TX, Typhlodromus occidentalis +TX, Verticillium lecanii +TX, Steinernema spp. +TX, Trichogramma +TX, Typhlodromus occidentalis +TX, Verticillium lecanii +TX, Steinernema spp. +TX, lecanii)+TX, apholanate+TX, bis(aziridine) methylaminophosphine sulfide (bisazir)+TX, busulfan+TX, dimatif+TX, hemel+TX, hemp+TX, metepa+TX, methiotepa+TX, methyl apholanate+TX, methyl oxazolidinone (methyl apholanate) ... apholate) + TX, morzid + TX, penfluron + TX, tepa + TX, thiohempa + TX, thiohempa + TX, trothamide + TX, urethaneimide + TX, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-eicos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodec-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX,4-Methylnonan-5-ol and 4-methylnonan-5-one + TX, α-polystyrene + TX, western pine beetle aggregation pheromone + TX, codlelure + TX, codlemone + TX, cuelure + TX, epoxide nonadecane + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, dodec-8 + TX, 10-10-dien-1-yl acetate + TX, dominicalure + TX, 4-methyloctanoic acid ethyl ester + TX, eugenol + TX, southern pine beetle aggregation pheromone (frontalin )+TX, grandlure+TX, grandlure I+TX, grandlure II+TX, grandlure III+TX, grandlure IV+TX, hexalure+TX, ipsdienol+TX, ipsenol+TX, japonilure+TX, lineatin+TX, litlure+TX, looplure+TX, medlure+TX, megatomoic acid+TX, methyl eugenol + TX, muscalure + TX, 18-decane-2,13-diene-1-yl acetate + TX, 18-decane-3,13-diene-1-yl acetate + TX, orfralure + TX, oryctalure + TX, ostramone + TX, siglure + TX, sordidin + TX, sulcatol + TX, tetradecane-11-ene -1-acetate + TX, Mediterranean fruit fly attractant + TX, Mediterranean fruit fly attractant A + TX, Mediterranean fruit fly attractant B1 + TX, Mediterranean fruit fly attractant B2 + TX, Mediterranean fruit fly attractant C + TX, trunc-call + TX, 2-(octylthio)-ethanol + TX, butopyronoxyl + TX, butoxy (polypropylene glycol) + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, DEET + TX, dimethyl carbate + TX, dimethyl phthalate + TX, ethyl hexanediol + TX, hexamide + TX, methoquin-butyl + TX, methyl neodecylamide + TX, oxamate + TX, picaridin + TX, 1-dichloro-1-nitroethane + TX,1,1-dichloro-2,2-di(4-ethylphenyl)-ethane + TX, 1,2-dichloropropane and 1,3-dichloropropylene + TX, 1-bromo-2-chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphonate Acid ester + TX, 2-imidazolidinone + TX, 2-isovaleryl indan-1,3-dione + TX, 2-methyl (prop-2-ynyl) aminophenyl methyl carbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yl dimethyl carbamate + TX, 4-methyl (prop-2-ynyl) amino-3,5-xylyl methyl carbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethyl carbamate + TX, acethion + TX, acrylonitrile + TX, aldrin + TX, alloamicin + TX, chloranil + TX, α-decandrin + TX, aluminum phosphide + TX, chloranil + TX, neonicotinoids + TX, ethyl athidathion + TX, methyl pyrifos + TX, Bacillus thuringiensis δ-endotoxin + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, fumonisin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, β-cyfluthrin + TX, β-cypermethrin + TX, bioethanomethrin + TX, biopermethrin + TX, bis (2-chloroethyl) ether + TX, borax + TX, bromophenazone + TX, bromo-DDT + TX, synthracen + TX, cypermethrin + TX, butathiofos + TX, butyl ester + TX, arsenic acid Calcium + TX, calcium cyanide + TX, carbon disulfide + TX, carbon tetrachloride + TX, cevadine + TX, borneol + TX, chlordane + TX, chlordecone + TX, chloroform + TX, chloropicrin + TX, chlornitrophos + TX, chlorprazophos + TX, cis-resmethrin + TX, cismethrin + TX, clocythrin (alias) + TX, copper acetoarsenite + TX, copper arsenate + TX, copper oleate + TX, coumithoate + TX, cryolite + TX, CS 708 + TX, benzonitrile + TX, cypermethrin + TX, pyrethroid + TX,Cypermethrin + TX, d-carbofuran + TX, DAEP + TX, dazomethane + TX, decarbofuran + TX, diamidafos + TX, isochlorphos + TX, dimethophos + TX, dicresyl + TX, cyclohexanil + TX, dieldrin + TX, diethyl 5-methylpyrazol-3-yl phosphate + TX, dilor + TX, tetrafluthrin + TX, dimethoate + TX, pyrethrin + TX, methylchlorfenapyr + TX, dichlorvos + TX, propanol + TX, pentotropol + TX, dinofuranoside + TX, benzylpyridin + TX, vegetable and fruit phosphorus + TX, thiopyraphos + TX, DSP + TX, ecdysterone + TX, EI 1642+TX, EMPC+TX, EPBP+TX, etaphos+TX, ethiobencarb+TX, ethyl formate+TX, ethylene dibromide+TX, ethylene dichloride+TX, ethylene oxide+TX, EXD+TX, ethiobencarb+TX, fenthion+TX, fenoxacrim+TX, cypermethrin+TX, fenthion+TX, ethylfenthion+TX, flucofuron+TX, butylfenthion+TX, phosphophos+TX, butylphosphine+TX, butylphosphine+TX, butylphosphine Cyclothion + TX, Furoxil + TX, Pyrethroid + TX, Biguanidine + TX, Biguanidine acetate + TX, Sodium tetrathiocarbonate + TX, Benzylfen + TX, HCH + TX, HEOD + TX, Heptachlor + TX, Cypermethrin + TX, HHDN + TX, Hydrogen cyanide + TX, Quinoline + TX, IPSP + TX, Chlorpheniramine + TX, Carbonyl + TX, Isochlor + TX, Isothiophos + TX, Transplanting + TX, Rice Blast + TX, Oxazophos + TX, Juvenile Hormone I + TX, Juvenile Hormone II + TX, Juvenile Hormone III + TX, chlorpentyl + TX, methoprene + TX, lead arsenate + TX, bromophenylphos + TX, acetamiprid + TX, thiamethoxam + TX, m-isopropyl methylcarbamate + TX, magnesium phosphide + TX, phosphorus azide + TX, methyl aphid + TX, aphidoxam + TX, mercurous chloride + TX, methyl sulfoxide + TX, metamethylenetetramine + TX, metamethylenetetramine + TX, potassium metamethylenetetramine + TX, sodium metamethylenetetramine + TX, methylsulfonyl fluoride + TX, butenylphos + TX, methoprene + TX, methylthiocyanate + TX, methoxychlor + TX, isothiocyanic acid Methyl ester + TX, methyl chloroform + TX, dichloromethane + TX, anthracene + TX, anticide + TX, naphthiophos + TX, naphthalene + TX, NC-170 + TX, nicotine + TX, nicotine sulfate + TX, nithiazine + TX, orthonicotine + TX, O-5-dichloro-4-iodophenyl O-ethylethyl phosphonothioate + TX, O,O-diethyl O-4-methyl-2-oxo-2H-benzopyran-7-ylphosphonothioate + TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphonothioate + TX,O,O,O',O'-Tetrapropyl dithiodipyrophosphate + TX, oleic acid + TX, p-dichlorobenzene + TX, methyl parathion + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, PH 60-38+TX, fenthion+TX, parachlorothion+TX, phosphine+TX, methyl phoxim+TX, methamidophos+TX, polychlorinated dicyclopentadiene isomers+TX, potassium arsenite+TX, potassium thiocyanate+TX, precocious element I+TX, precocious element II+TX, precocious element III+TX, amidophos+TX, profluthrin+TX, fenthion+TX, pyraclostrobin+TX, anti-pyrethroid+TX, quassia extract+TX, quinalphos-methyl+TX, oxazolidinone+TX, iodophos+TX, resmethrin+TX, rotenone+TX, thiamethoxam+TX, ryanodine+TX, ryanodine+TX, Sabadilla + TX, octamethrin + TX, clostridium + TX, SI-0009 + TX, thiopropionitrile + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoride + TX, sodium hexafluorosilicate + TX, sodium pentachlorophenol + TX, sodium selenate + TX, sodium thiocyanate + TX, sulcofuron + TX, sulcofuron-sodium + TX, sulfuryl fluoride + TX, thiopromide + TX, tar + TX, thiocarb + TX, TDE + TX, butylpyrimidinphos + TX, dimethoate + TX, cyclopentylthrin + TX, tetrachloroethane + TX, thiochlorvos + TX, Insect ring + TX, insect ring oxalate + TX, cypermethrin + TX, cypermethrin + TX, cypermethrin sodium + TX, tetrabromothrin + TX, permethrin + TX, trichlormetaphos-3 + TX, chlorpyrifos + TX, cyclohexanil + TX, trichlormetaphos-3 + TX, chlorpyrifos + TX, tolprocarb + TX, chlorpyrifos + TX, methoxam + TX, veratridine + TX, veratridine + TX, XMC + TX, zetamethrin + TX, zinc phosphide + TX, tolfenphos + TX, and cypermethrin + TX, tetrafluthrin + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, ferric phosphate + TX, niclosamide-ethanolamine + TX, tributyltin oxide + TX, pyromorph + TX, snail killer + TX, 1,2-dibromo-3-chloropropane + TX, 1,3-dichloropropylene + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6-thio-1,3,5-thiadiazin-3-yl acetic acid + TX, 6-isopentenylaminopurine + TX, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine + TX, benclothiaz + TX, cytokinin + TX, DCIP + TX, furfural + TX,Isamidofos + TX, kinetin + TX, verrucospore mycorrhizal composition + TX, tetrachlorothiophene + TX, xylenol + TX, zeatin + TX, potassium ethyl xanthate + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, Polygonum cuspidatum extract + TX, α-chlorohydrin + TX, antu + TX, barium carbonate + TX, bismuth urea + TX, brodifacoum + TX, bromodiolone + TX, bromodiolone + TX, chloranil + TX, cholecalciferol + TX, chlorfenapyr + TX, cypermethrin + TX, cypermethrin + TX, cypermethrin + TX, fodoxime + TX, thiazolin + TX, difacoum + TX, calciferol + TX, fludioxime + TX, fluoroacetamide + TX, fludioxidine + TX, fludioxidine hydrochloride + TX, fodoxime + TX, phosphorus + TX, warfarin + TX, warfarin + TX, scopol glycoside + TX, sodium -fluoroacetate + TX, thallium sulfate + TX, warfarin + TX, -2-(2-butoxyethoxy)ethyl piperate + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, farnesol with nerolidol + TX, synergistic acetylene ether + TX, MGK 264+TX, piperonyl butoxide+TX, synergistic aldehyde+TX, propyl isomer+TX, S421+TX, synergistic powder+TX, sesasmolin+TX, sulfoxide+TX, anthraquinone+TX, copper cyclohexaneate+TX, copper oxychloride+TX, dicyclopentadiene+TX, serene+TX, zinc cyclohexaneate+TX, zinc thiram+TX, imanin+TX, ribavirin+TX, mercuric oxide+TX, thiophanate-methyl+TX, azaconazole+TX, bifenthrin+TX, oxadiazole+TX, cyproconazole+TX, fenpropimorph+TX, diniconazole-+TX, epoxiconazole+TX, fenbuconazole+TX, fluquinconazole+TX, flusilazole+TX, flutriafol+TX, furopyram+TX, hexaconazole+TX, imazalil-+TX, imipenem+TX, cyproconazole+TX, metconazole+TX, myclobutanil+TX , paclobutrazol + TX, pyriclobutrazol + TX, penconazole + TX, prothioconazole + TX, pyrifenox + TX, prochloraz + TX, propiconazole + TX, pyraclostrobin + TX, simeconazole + TX, tebuconazole + TX, fluconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, trichlorfon + TX, pyrimidine + TX, chlorfenapyr + TX, flufenapyr + TX, bupirimate + TX, dimethirimol + TX, ethirimol + TX, dodecacyclic morpholine + TX, fenpropidine + TX, fenpropimorph + TX, spiroxaplanol + TX, tridecamorph + TX, cyprodinil + TX, pyrimidine + TX,Pyrimethanil + TX, fenpiclonil + TX, fludioxonil + TX, benalaxyl + TX, furalaxyl + TX, -metalaxyl- + TX, R-metalaxyl + TX, furamide + TX, oxadixyl + TX, carbendazim + TX, debacarb + TX, oxadixyl- + TX, thiabendazole + TX, chlozolinate + TX, dichlozoline + TX, myclozoline- + TX, procymidone + TX, vinclozoline ozoline)+TX, boscalid+TX, carboxin+TX, furamide+TX, flutolanil+TX, oxamoxadine+TX, penthiopyrad+TX, thiofuran+TX, dodine+TX, biguanide+TX, azoxystrobin+TX, enestroburin+TX, enestroburin+TX, flutolanil+TX, fluoxastrobin+TX, enestroburin+TX, fluoxastrobin+TX, enestroburin+TX, oxamoxadine+TX, oxamoxadine+TX, oxamoxadine+TX, pyraclostrobin+TX, pyraclostrobin+TX, fumei Iron + TX, mancozeb + TX, maneb + ​​TX, metiram + TX, methyl propineb + ​​TX, mancozeb + TX, captan + TX, oxazolidinone + TX, folpet + TX, tolylfluanid + TX, Bordeaux mixture + TX, copper oxide + TX, mancozeb + TX, quinoline copper + TX, phthalocyanine + TX, kefansan + TX, isoblastic acid + TX, chlorpyrifos + TX, methyl tolclofos + TX, captan + TX, benzathine + TX, blasticidin-S + TX, chloroneb + ​​TX, chlorothalonil + TX, cyfluanid + TX, cymoxanil + TX, cypermethrin + TX, diclofenac + TX cymet + TX, diclomezine + TX, dicloran + TX, diethofencarb + TX, oxadiazine + TX, flumorph + TX, dithianon + TX, ethaboxam + TX, etridiazole + TX, oxadiazine + TX, fenamidone + TX, fenoxanil + TX, ferimzone + TX, fluazinam + TX, fluopicolide + TX,Flusulfamide + TX, flupyraclostrobin + TX, -fenacet + TX, fosetyl-aluminium + TX, hymexazol + TX, propineb + ​​TX, cyazofamid + TX, methasulfocarb + TX, mefenacet + TX, pencycuron + TX, phthalide + TX, polyoxins + TX, propamocarb + TX, pyrimidine + TX, proquinazid + TX, pyroquilon )+TX, pyriofenone+TX, quinoxyfenone+TX, pentachloronitrobenzene+TX, thiazolamide+TX, triazoxide+TX, tricyclazole+TX, quinazoline+TX, validamycin+TX, valeramide+TX, zoxamide+TX, mandipropamid+TX, fluorophenyletheramide+TX, isopyrazam+TX, sedaxane+TX, benzovintriazole+TX, fluoropyraclostrobin+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2- 1,2-c]isothiazol-3-carbonitrile + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carbonitrile + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6 -Fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine+TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine+TX, fluindapyr+TX, Jiaxiangjunzhi+TX, lvbenmixianan+TX, dichlobentiazox+TX, mandestrobin+TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone+TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol+TX,Oxathiapiprolin + TX, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamic acid tert-butyl ester + TX, pyraziflumid + TX, inpyrfluxam + TX, trolprocarb + TX, clofoconazole + TX, ipfentrifluconazole + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4 -(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate + TX, N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamic acid but-3-ynyl ester + TX, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamic acid methyl + TX, 3-chloro-6-methyl-5- Phenyl-4-(2,4,6-trifluorophenyl)pyridazine+TX, pyridachlometyl+TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide+TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazolyl-5-one+TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazolyl-5-one+TX, aminopyrifen+TX, pyraclostrobin+TX, indazolesulfazoline+TX, fluopicolide+TX, (Z,2E)- 5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine+TX, florylpicoxamid+TX, fenpicoxamid+TX, isobutylethoxyquinoline+TX, ipflufenoquin+TX, quinofumelin+TX, isopropylthiocyanate+TX, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide+TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide+TX, benzathiostrobin+TX,Cyanoconazole + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, fluopyram + TX, fluthiazolinil + TX, fluopyram + TX, pyrapropoyne + TX, picarbutrazox + TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2, 4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile+TX, metyltetraprole+TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide+TX, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-diphenyl]-4-yl]-5-pyrimidinemethanol+TX, fluoxapiprolin+TX, enoxastrobin+TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazole-1- 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile+TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile+TX, trinexapac-ethyl+TX, syringoxystrobin+TX, zhongshengmycin+TX, thiophanate-copper+TX, thiazole zinc+TX, amectotractin+TX, iprodione+TX X; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX,N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared by WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared by the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared by the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX (these compounds can be prepared by WO 2019 / 110427); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline+TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline+TX, 4,4-difluoro-3,3-dimethyl -1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline+TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline+TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline+TX (these compounds can be prepared by WO 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX,3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole+TX (these compounds can be prepared by the method described in WO 2016 / 156085); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide+TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide+TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide+TX, )-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-ethyl-1-methoxy-1-[[4-[ 5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea+TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide+TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one+TX, 5,5-dimethyl-2-[[4-[5 -(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one+TX, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester+TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine+TX. The compounds in this paragraph can be prepared from WO 2017 / 055473, WO 2017 / 055469,WO 2017 / 093348 and WO 2017 / 118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol+TX (the compound can be prepared by the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol+TX (the compound can be prepared by the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile+TX (the compound can be prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (the compound can be prepared by the method described in WO2016 / 156290); 2-amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxyphenyl) methyl ester + TX (the compound can be prepared by the method described in WO2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraketone + TX (this compound can be prepared by the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine+TX (this compound can be prepared by the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine+TX; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine+TX (this compound can be prepared by the method described in WO 2-(Difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide+TX (this compound can be prepared by the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone+TX,(3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX (these compounds can be prepared by the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX (this compound can be prepared by the method described in WO2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester + TX (this compound can be prepared by the method described in WO 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide+TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX, N-[N-methoxy-C-methyl-carbonimide]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX (these compounds can be prepared by the method described in WO 2018 / 202428),

[0053] N'-(2-chloro-S-methyl-4-phenoxyphenyl)-N-ethyl-N-methyliminocarboxamide + TX,

[0054] N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyliminocarboxamide + TX,

[0055] N'-[2-chloro-4-(3-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyliminocarboxamide + TX,

[0056] N'-(2-bromo-S-methyl-4-phenoxyphenyl)-N-ethyl-N-methyliminocarboxamide + TX,

[0057] N'-[2-bromo-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyliminocarboxamide + TX,

[0058] N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-isopropyl-N-methyliminocarboxamide + TX,

[0059] N'-[4-(2-cyanophenoxy)-2-methyl-5-(trifluoromethyl)phenyl]-N-ethyl-N-methyliminocarboxamide + TX,

[0060] N'-[5-bromo-2-methyl-4-(2-methylphenoxy)phenyl]-N-ethyl-N-methyliminocarboxamide + TX,

[0061] N-ethyl-N'-[4-(2-fluorophenoxy)-2-methyl-5-(trifluoromethyl)phenyl]-N-methyliminocarboxamide (these compounds can be prepared by the method described in WO 2018 / 108977) + TX,

[0062] N-(1-ethylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0063] N-(2-isopropylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0064] N-(2-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0065] N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0066] N-(2-ethylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0067] N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared by the method described in WO 2019 / 115511) + TX,

[0068] N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0069] N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0070] N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0071] N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropanecarboxamide+TX, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX,

[0072] 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX,

[0073] N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide + TX,

[0074] N-[N-methoxy-C-methyl-carbonimido]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0075] N-[(Z)-N-methoxy-C-methyl-carbonimido]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0076] N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acrylamide + TX,

[0077] 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one+TX,

[0078] N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenethioamide + TX,

[0079] 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one+TX,

[0080] (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX,

[0081] (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX,

[0082] 2,6-Dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone + TX,

[0083] N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenethioamide + TX,

[0084] N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,

[0085] (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine + TX,

[0086] N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX,

[0087] N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX,

[0088] N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX,

[0089] N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX,

[0090] 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol+TX,

[0091] 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol+TX,

[0092] 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX,

[0093] 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX,

[0094] 2-(Difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX,

[0095] 2-(Difluoromethyl)-N-[(3R)-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-3-pyridinecarboxamide + TX,

[0096] Methyl (E)-3-methoxy-2-[2-[(5-methoxy-1,3-benzothiazol-2-yl)sulfanylmethyl]phenyl]prop-2-enoate + TX,

[0097] 2-Chloro-N-(4'-chloro[1,1'-diphenyl]-2-yl)-3-pyridinecarboxamide + TX,

[0098] 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX,

[0099] 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX,

[0100] 3-(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazole 1,1-dioxide + TX,

[0101] (3S,6S,7R,8R)-8-benzyl-3-{3-[(isobutyryloxy)methoxy]-4-methoxypyridine-2-carboxamido}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate + TX,

[0102] [(1S)-2,2-bis(4-fluorophenyl)-1-methyl-ethyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + TX,

[0103] 3-(Difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide + TX,

[0104] [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate + TX,

[0105] 3-(Difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX,

[0106] (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol+TX,

[0107] 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol + TX, N-[1,1-dimethyl-2-(4-isopropoxy-o-tolyl)-2-oxyethyl]-3-methylthiophene-2-carboxamide + TX,

[0108] N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide + TX,

[0109] 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl-acetamide + TX,

[0110] (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol+TX,

[0111] 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazolyl-5-one + TX,

[0112] (Z)-N-{2-[3-chloro-5-(cyclopropylethynyl)-2-pyridyl]-2-(isopropoxyimino)ethyl}-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + TX,

[0113] N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide + TX,

[0114] 3-Chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine + TX,

[0115] 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinoline + TX,

[0116] N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX,

[0117] N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX,

[0118] Avermectin + TX, acetamiprid + TX, acetamiprid + TX, flumethrin + TX, Acynonapyr + TX, bifenthrin + TX, afolan + TX, cotton bell carbendazim + TX, allethrin + TX, cis-cypermethrin + TX, alpha-cypermethrin + TX, sulfamethoxazole + TX, cypermethrin + TX, triazotin + TX, sulfanilamide + TX, benzylchlor + TX, benzylchlor + TX, Benzpyrimoxan + TX, β-cypermethrin + TX, β-cypermethrin + TX, bifenazate + TX, bifenthrin + TX, binachlor + TX, bio-allethrin + TX, bio-allethrin S)-cyclopentyl isomer + TX, bio-resmethrin + TX, bistrifluan + T X, Broflanilide + TX, Bromothrin + TX, Bromophos-ethyl + TX, Buprofezin + TX, Butanone + TX, Cadrenophos + TX, Carbaryl + TX, Butansulfuron + TX, Badan + TX, CAS No.: 1472050-04-6 + TX, CAS No.: 1632218-00-8 + TX, CAS No.: 1808115-49-2 + TX, CAS No.: 2032403-97-5 + TX, CAS No.: 2044701-44-0 + TX, CAS No.: 2128706-05-6 + TX, CAS No.: 2249718-27-0 + TX, Chlorantraniliprole + TX, Chlordane + TX , chlorfenapyr + TX, chloranil + TX, chlorfenapyr + TX, clenpyr + TX, chlorfenapyr + TX, clothianidin + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, benzonitrile + TX, cyantraniliprole + TX, cyclobrominamide + TX, pyrethroids + TX, cyclohexidine + TX, cyclohexidine + TX, cypermethrin + TX, cyfluthrin + TX, cyhalodiamide + TX, cyhalothrin + TX, cypermethrin + TX, cyfluthrin + TX, cypermethrin + TX, cyfluthrin + TX, cypermethrin + TX, cyfluthrin + TX, cypermethrin + TX, cypermethrin + TX, Phosphorus chlormequat + TX, Dibrom + TX, Dicloromezotiaz + TX, Fluomezozinc + TX, Diflubenzuron + TX, Dipropyridaz + TX, Diactivin + TX, Dimethoate + TX, Dinotefuran + TX, Vegetable phosphorus + TX, Emamectin + TX, Dextran + TX, ε-momfluorothrin + TX, ε-Methiofluthrin + TX, Cypermethrin + TX, Ethion + TX, Ethiopromide + TX, Ethofenapyr + TX, Ethozolin + TX, Ethiopromide + TX, Fenamiphos + TX, Penfluthrin + TX, Fenitrothion + TX, Fenbuterol + TX, Fenoxycarb + TX, Cypermethrin + TX,Fenpyroxymate + TX, Fensulfuron + TX, Fenthion + TX, Yesalin + TX, Cypermethrin + TX, Fipronil + TX, Flometoquin + TX, Flyoxalamide + TX, Flyoxaline + TX, Fluazaindolizine + TX, Flufenac + TX, Fluflufenamide + TX, Flucitrinate + TX, Flufenac + TX, Flucythrin + TX, Fluthiazolin + TX, Flumethrin + TX, Trifluthrin + TX, Butene Fipronil + TX, Fluhexafon + TX, Flucythrin + TX, Fluopyram + TX, Flupentiofenox +TX, Flupyrimin+TX, Flupyrimin+TX, Fluralaner+TX, Fluvalinate+TX, Fluxametamide+TX, Thiathiathion+TX, γ-Cyhalothrin+TX, GossyplureTM+TX, Pentofenguanyl+TX, Chlorfenapyr+TX, Chlorfenapyr+TX, Halofenprox+TX, Heptafluthrin+TX, Hexythiazox+TX, Hydrazine+TX, Imicyafos+TX, Imidacloprid+TX, Imidacloprid+TX, Indoxacarb+TX, Methyl iodide+TX, Iprodione+TX, Isocycloser am+TX, isothiocarb+TX, ivermectin+TX, κ-bifenthrin+TX, κ-tefluthrin+TX, λ-cyhalothrin+TX, lepidomectin+TX, chlorfenuron+TX, metaflumizone+TX, metaldehyde+TX, metamectin+TX, methomyl+TX, methoxyfenozide+TX, methoxyfluthrin+TX, cypermethrin+TX, cypermethrin+TX, cypermethrin+TX, cypermethrin+TX, cypermethrin+TX, cypermethrin+TX, cypermethrin+TX, cypermethrin+TX, momfluorothrin+TX, cypermethrin+TX, nitenpyram+TX, nithiazine+TX, oxydemeton-methyl+TX, oxamectin+TX, oxazolidinone ... X, pirimicarb + TX, pyrimidinephos-ethyl + TX, polyhedrosis virus + TX, prallethrin + TX, profenofos + TX, profenofos + TX, profluthrin + TX, propargyl + TX, amine propanil + TX, propoxur + TX, prothiophos + TX, protrifenbute + TX, pyflubumide + TX, pymetrozine + TX, pyraclostrobin + TX, pyrafluprole + TX, pyridaben + TX, pyrifluquinazon + TX, pyrimidine + TX, pyrimostrobin + TX, pyraflufen + TX,Resmothrin + TX, Sarolaner + TX, Selamectin + TX, Fluosimethrin + TX, Ethyl Spinetoram + TX, Spinetoram + TX, Spirodiclofen + TX, Spiromesib + TX, Spiropyrim + TX, Spiropyrim + TX, Spirotetramat + TX, Sulfonamidin + TX, Tebufenazide + TX, Tebufenpyrad + TX, Tebupirimiphos + TX, Tefluthrin + TX, Tetrachloraniliprole + TX, Tetradiphon + TX, Tetramethrin + TX, Tetrafluthrin + TX, Cypermethrin + TX, Cypermethrin + TX, Flucythramide + TX, θ-Cypermethrin + TX, Thiacloprid + TX, Thiamethoxam + TX, Cypermethrin + TX, Thiamethoxam + TX, Thiocyclan + TX, Thiodicarb + TX, Long-acting Carb + TX, Methyl Ethophos + TX, Cypermethrin + TX, Tio xazafen+TX, tolfenpyrad+TX, toxaphene+TX, tralomethrin+TX, transfluthrin+TX, thiamethoxam+TX, triazophos+TX, trichlorfon+TX, chlorpyrifos+TX, trichlorfon+TX, triflumezopyrim+TX, Tyclopyrazoflor+TX, ζ-cypermethrin+TX, seaweed extract and fermentation products derived from sugar acyl+TX, seaweed extract and fermentation products derived from sugar acyl (containing urea+TX, amino acids+TX, potassium and molybdenum, and EDTA-chelated manganese+TX), seaweed extract and fermented plant products+TX, seaweed extract and fermented plant products (containing plant hormones+TX, vitamins+TX, EDTA-chelated copper+TX, zinc+TX, and iron+TX), azadirachtin+TX, Bacillus ayuzawa (Bacillus aizawai) + TX, Bacillus chitinosporus AQ746 (NRRL Accession No. B-21 618) + TX, Bacillus firmus + TX, Bacillus kurstaki + TX, Bacillus mycoides AQ726 (NRRL Accession No. B-21664) + TX, Bacillus pumilus (NRRL Accession No. B-30087) + TX, Bacillus pumilus AQ717 (NRRL Accession No. B-21662) + TX, Bacillus species AQ178 (ATCC Accession No. 53522) + TX, Bacillus Species AQ175 (ATCC Accession No. 55608) + TX, Bacillus species AQ177 (ATCC Accession No. 55609) + TX, unspecified Bacillus subtilis + TX, Bacillus subtilis AQ153 (ATCC Accession No. 55614) + TX, Bacillus subtilis AQ30002 (NRRL Accession No. B-50421) + TX, Bacillus subtilis AQ30004 (NRRL Accession No. B-50455) + TX,Bacillus subtilis AQ713 (NRRL registration number B-21661) + TX, Bacillus subtilis AQ743 (NRRL registration number B-21665) + TX, Bacillus thuringiensis AQ52 (NRRL registration number B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL registration number B-21530) + TX, Bacillus thuringiensis subspec. kurstaki BMP 123 + TX, Beauveria bassiana + TX, D-limonene + TX, granulovirus + TX, Harpin + TX, Helicoverpa armigera nuclear polyhedrosis virus + TX, Helicoverpa tatarinowii nuclear polyhedrosis virus + TX, Helicoverpa viridis nuclear polyhedrosis virus + TX, Helicoverpa viridis nuclear polyhedrosis virus + TX, Metarhizium species + TX, Muscodor albus 620 (NRRL registration number 30547) + TX, Muscodor roseus A3-5 (NRRL registration number 30548) + TX, neem-based products + TX, Paecilomyces fumosorum + TX, Paecilomyces lilacinus + TX, Pasteuria szabalensis + TX, Pasteuria penetrantis + TX, Pasteuria thornei + TX, Pasteuria thornei + TX, p-cymene + TX, Plutella xylostella granulosis virus + TX, Plutella xylostella nuclear polyhedrosis virus + TX, polyhedrosis virus + TX, pyrethrum + TX, QRD 420 (terpenoid blend) + TX, QRD452 (terpenoid blend) + TX, QRD460 (terpenoid blend) + TX, Quillaja saponaria + TX, Rhodococcus sphaeroides AQ719 (NRRL registration number B-21663) + TX, Spodoptera frugiperda nuclear polyhedrosis virus + TX, Streptomyces flavus (NRRL registration number 30232) + TX, Streptomyces species (NRRL registration number B-30145) + TX, terpenoid blend + TX, Verticillium species + TX, N-octyl-N'-[2-(octylamino)ethyl]ethane-1,2-diamine + TX, chloroindole hydrazide + TX, spidoxamat + TX, cintamidine + TX, cyprofenamide + TX, cypr ofluoranilide+TX, fluorophenyletheramide+TX, fluconazole+TX, gemflutioconazole+TX, hydroxytioconazole+TX, pyrimidine fungicide (flumetylsulforim)+TX, chloroindole hydrazide+TX, methylpyrimidine (metarylpicoxamid)+TX, toluolpicoxamid+TX, flufenoxadiazam+TX, nicofluprole+TX, 2-(3-ethylsulfonyl-2-pyridyl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine+TX,1-[6-(2,2-difluoro-7-methyl-[1,3]dioxol[4,5-f]benzimidazol-6-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitrile + TX, racemic-(2Z)-2-[2-fluoro-5-[hydroxy(2,2,2-trifluoroethyl)-λ4-sulfanyl]-4-methyl-phenyl]imino-3-(2,2,2-trifluoroethyl)thiazolidin-4-one-ethane + TX.

[0119] The formulation typically comprises a liquid or solid carrier and optionally one or more conventional formulation adjuvants, which may be solid or liquid adjuvants, for example, non-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (e.g., silicone oils), preservatives, clays, inorganic compounds, viscosity modifiers, surfactants, binders and / or tackifiers. The composition may further comprise fertilizers, micronutrient donors or other preparations that influence plant growth, and comprises combinations containing the compounds of the invention and one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides and insecticides.

[0120] The compositions are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid compound according to the invention, and in the presence of at least one auxiliary, for example by intimately mixing and / or grinding the compound according to the invention with one or more auxiliary agents. In the case of the solid compounds according to the invention, the grinding / milling of the compound is to ensure a specific particle size.

[0121] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersions, directly sprayable or dilutable solutions, spreadable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or capsules in a polymeric substance, these compositions comprising at least a compound as defined in any one of embodiments 1 to 14 and the type of composition being chosen to suit the intended purpose and the prevailing circumstances.

[0122] Typically, the composition comprises 0.1% to 99% (especially 0.1% to 95%) of a compound as defined in any one of Examples 1 to 14 and 1% to 99.9% (especially 5% to 99.9%) of at least one solid or liquid carrier, and it is usually possible that 0 to 25% (especially 0.1% to 20%) of the composition is a surfactant (% means percentage by weight in each case). Although for commercial products, concentrated compositions tend to be preferred, the final consumer usually uses a dilute composition with a significantly lower concentration of active ingredients.

[0123] Examples of leaf formulation types for use in premix compositions are:

[0124] GR: Granules

[0125] WP: Wettable Powder

[0126] WG: Water dispersible granules (powder)

[0127] SG: Water-soluble granules

[0128] SL: Soluble Concentrate

[0129] EC: Emulsifiable Concentrate

[0130] EW: Oil in water emulsion

[0131] ME: Microemulsion

[0132] SC: Aqueous Suspension Concentrate

[0133] CS: Aqueous Capsule Suspension

[0134] OD: Oil-based suspension concentrates, and

[0135] SE: aqueous suspension emulsion.

[0136] While examples of the types of seed treatment formulations useful in premix compositions are:

[0137] WS: Wettable powder for seed treatment slurry

[0138] LS: Solution for seed treatment

[0139] ES: Emulsion for seed treatment

[0140] FS: Suspension concentrate for seed treatment

[0141] WG: water dispersible granules, and

[0142] CS: aqueous capsule suspension.

[0143] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions or mixtures thereof, and dusts.

[0144] In view of the nature of the formulation, the application method (such as foliar application, drenching application, spraying application, atomization application, dusting application, broadcasting application, coating application or pouring application) can be selected according to the intended purpose and the prevailing circumstances.

[0145] Tank-mix compositions are generally prepared by diluting one or more premix compositions containing different pesticides and optionally additional adjuvants with a solvent (eg, water).

[0146] Suitable carriers and adjuvants can be solid or liquid and are the substances customary in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0147] Generally, tank-mix formulations for foliar or soil application contain 0.1% to 20% (especially 0.1% to 15%) of the desired ingredients and 99.9% to 80% (especially 99.9% to 85%) of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 20% (especially 0.1% to 15%) based on the tank-mix formulation.

[0148] Typically, premix formulations for foliar application contain 0.1% to 99.9% (especially 1% to 95%) of the desired ingredient and 99.9% to 0.1% (especially 99% to 5%) of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 50% (especially 0.5% to 40%) based on the premix formulation.

[0149] Typically, tank-mix formulations for seed treatment applications contain 0.25% to 80% (especially 1% to 75%) of the desired ingredients and 99.75% to 20% (especially 99% to 25%) of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 40% (especially 0.5% to 30%) based on the tank-mix formulation.

[0150] Typically, premix formulations for seed treatment applications contain 0.5% to 99.9% (especially 1% to 95%) of the desired ingredients and 99.5% to 0.1% (especially 99% to 5%) of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 50% (especially 0.5% to 40%) based on the premix formulation.

[0151] Whereas commercial products will preferably be formulated as concentrates (eg, premix compositions (formulations)), the end user will typically use a diluted formulation (eg, a tank-mix composition).

[0152] Preferred seed treatment premix formulations are aqueous suspension concentrates. Conventional treatment techniques and machines, such as fluidized bed technology, drum milling methods, rotostatic seed treatment machines and drum coating machines, can be used to apply the formulation to the seeds. Other methods (such as spouted beds) may also be useful. The seeds may be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compound of the present invention is particularly suitable for use in soil and seed treatment applications.

[0153] Typically, the premix composition of the present invention contains 0.5% to 99.9% by mass, especially 1% to 95%, advantageously 1% to 50% of the desired ingredients and 99.5% to 0.1% by mass, especially 99% to 5% by mass of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant (or adjuvant) may be a surfactant, in an amount of 0 to 50% by mass, especially 0.5% to 40%, based on the mass of the premix formulation.

[0154] In addition, further, other biocidal active ingredients or compositions can be combined with the composition of the present invention, and used in the method of the present invention and applied simultaneously or sequentially with the composition of the present invention. When applied simultaneously, these other active ingredients can be prepared or mixed in, for example, a spray tank together with the composition of the present invention. These other biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0155] In addition, the compositions of the invention may also be administered with one or more inducers of systemic acquired resistance ("SAR" inducers). SAR inducers are known and described, for example, in U.S. Pat. No. 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[0156] The compounds as defined in any one of Examples 1 to 14 are usually used in the form of compositions and can be applied to crop areas or plants to be treated simultaneously or sequentially with other compounds. For example, these other compounds can be fertilizers or micronutrient donors or other preparations that affect plant growth. They can also be selective herbicides or non-selective herbicides, together with insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with other carriers, surfactants or adjuvants that are commonly used in the field of formulations to promote application.

[0157] The compounds of formula (I) can be used in the form of (fungicidal) compositions for controlling or protecting against the plant pathogen Coryneformis multilocus, which compositions comprise at least one compound as defined in any one of Examples 1 to 14 as active ingredient (in free form or in the form of an agrochemically acceptable salt) and at least one of the above-mentioned adjuvants.

[0158] Plants and / or target crops according to the invention include conventional as well as genetically enhanced or genetically engineered varieties, such as, for example, insect-resistant (e.g., Bt. and VIP varieties) as well as disease-resistant, herbicide-tolerant (e.g., glyphosate-resistant and glufosinate-resistant corn varieties, marketed under the trade names and Commercially available) and nematode-tolerant varieties. By way of example, suitable genetically enhanced or genetically engineered crop varieties include Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.

[0159] The terms "plants" and / or "target crops" are to be understood as also including plants which have been rendered tolerant to herbicides such as bromoxynil or classes of herbicides such as, for example, HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors as a result of conventional methods of breeding or genetic engineering. Examples of crops which have been rendered tolerant to imidazolinones such as imazamox by conventional methods of breeding (mutagenesis) are Summer rapeseed (canola). Examples of crops that have been rendered tolerant to herbicides or herbicides by genetic engineering methods include glyphosate-resistant and glufosinate-resistant maize varieties, which are based on and Commercially available under the trade name ANTIQUID®.

[0160] The terms "plants" and / or "target crops" are to be understood as including those that are naturally or have been rendered resistant to harmful insects. This includes plants that have been transformed using recombinant DNA technology so as to, for example, synthesize one or more selectively acting toxins, such as are known from, for example, toxin-producing bacteria. Examples of toxins that may be expressed include delta-endotoxins, vegetative insecticidal proteins (Vips), insecticidal proteins of bacterial colonizing nematodes, and toxins produced by scorpions, arachnids, wasps and fungi. Examples of crops that have been modified to express Bacillus thuringiensis toxins are Bt maize, Bt thuringiensis toxins ... (Syngenta Seeds). Examples of crops that include more than one gene encoding insecticide resistance and thereby expressing more than one toxin are (Syngenta Seeds). Crops or their seed material may also be resistant to multiple types of pests (so-called stacked transgenic events when produced by genetic modification). For example, a plant may have the ability to express an insecticidal protein while being tolerant to a herbicide, such as Herculex (Dow AgroSciences, Pioneer Hi-Bred International).

[0161] The term "plants" and / or "target crops" is to be understood as also including plants which have been transformed by the use of recombinant DNA techniques so that they are able to synthesize selectively active antipathogenic substances, such as, for example, so-called "pathogenesis-related proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants which are able to synthesize such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818 and EP-A-0 353 191. Methods for producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

[0162] Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vips), for example Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins of bacterial colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus spp. luminescens), Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins and other insect-specific neurotoxins; toxins produced by fungi, such as streptomycin, plant lectins, such as pea agglutinin, barley agglutinin or snowdrop agglutinin; agglutinin; protease inhibitors, such as trypsin inhibitors, silk proteinase inhibitors, potato glycoproteins, cystatins, papaya Protease inhibitors; ribosome inactivating proteins (RIPs), such as ricin, maize-RIP, abrin, luffa seed toxin, saponin or bryophyllin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysteroid inhibitors, HMG-COA-reductase, ion channel blockers such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0163] Further, in the context of the present invention, delta-endotoxins (e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C) or vegetative insecticidal proteins (Vips) (e.g., Vip1, Vip2, Vip3 or Vip3A) are understood to include obviously also mixed toxins, truncated toxins and modified toxins. Mixed toxins are recombinantly produced by new combinations of different domains of those proteins (see, e.g., WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, it is preferred that a non-naturally occurring protease recognition sequence is inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0164] Further examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed in, for example, EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073.

[0165] Methods for preparing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367474, EP-A-0 401 979 and WO 90 / 13651.

[0166] The toxins contained in the transgenic plants render the plants tolerant to harmful insects. Such insects can be found in any insect taxonomic group, but are particularly common among beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera).

[0167] Transgenic plants comprising one or more genes encoding insecticide resistance and expressing one or more toxins are known and some of them are commercially available. Examples of such plants are: (corn variety expressing Cry1Ab toxin); YieldGard (corn variety expressing Cry3Bb1 toxin); YieldGard (corn varieties expressing Cry1Ab and Cry3Bb1 toxins); (corn variety expressing Cry9C toxin); Herculex (a corn variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) that confers tolerance to the herbicide glufosinate ammonium); NuCOTN (cotton variety expressing Cry1Ac toxin); Bollgard (cotton variety expressing Cry1Ac toxin); Bollgard (cotton varieties expressing Cry1Ac and Cry2Ab toxins); (cotton varieties expressing Vip3A and Cry1Ab toxins); (potato variety, expressing Cry3A toxin); GT Advantage (GA21 glyphosate tolerance trait), CB Advantage (Bt11 corn borer (CB) trait) and

[0168] Further examples of such genetically modified crops are:

[0169] 1. Bt11 corn, from Syngenta Seeds SAS, Chemin del'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) resistant to attack by European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of a truncated Cry1Ab toxin. Bt11 corn also transgenic expression of the PAT enzyme to obtain tolerance to the herbicide glufosinate ammonium.

[0170] 2. Bt176 corn, from Syngenta Seeds, 27 Hobbit Road, F-31 790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, which is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of the Cry1Ab toxin. Bt176 corn also transgenic expression of the PAT enzyme to obtain tolerance to the herbicide glufosinate ammonium.

[0171] 3. MIR604 corn, from Syngenta Seeds, 27 Rue Hobbitt, F-31790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. Corn rendered insect resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic corn plants is described in WO 03 / 018810.

[0172] 4. MON 863 maize, from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain coleopteran insects.

[0173] 5. IPC 531 Cotton, from Monsanto Europe NV, 270-272 Avenue Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0174] 6.1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1F for resistance to certain lepidopteran insects and the protein PAT for tolerance to the herbicide glufosinate ammonium.

[0175] 7. NK603×MON 810 maize, from Monsanto Europe, 270-272 Avenue Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. It is a conventionally bred hybrid maize variety made by crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 maize transgenically expresses the CP4 EPSPS protein obtained from the Agrobacterium sp. strain CP4, which confers resistance to herbicides. The strain also expresses the CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki, which confers tolerance to certain lepidopteran insects, including the European corn borer.

[0176] As used herein, the term "locus" means a place where or on which plants grow, or where seeds of cultivated plants are sown, or where seeds are to be placed in the soil. It includes soil, seeds, and seedlings, together with established vegetation.

[0177] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0178] The term "plant propagation material" is understood to mean the reproductive parts of plants, such as seeds (which can be used for the propagation of plants), and vegetative materials, such as cuttings or tubers (e.g. potatoes). For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants may be mentioned. Germinated plants and young plants that will be transplanted after germination or after emergence may also be mentioned. These young plants may be treated completely or partially by dipping and protected before transplanting. Preferably, "plant propagation material" is understood to mean seeds.

[0179] Pesticides referred to herein using their common names are known, for example, from “The Pesticide Manual”, 15th edition, British Crop Protection Council 2009.

[0180] The compound for use in the method of the invention as defined in any one of Examples 1 to 14 can be the sole active ingredient of the composition, or it can be mixed with one or more additional active ingredients (such as pesticides, fungicides, synergists, herbicides or plant growth regulators) as appropriate. In some cases, the additional active ingredients can produce unexpected synergistic activity.

[0181] The compositions according to the invention may also contain further solid or liquid adjuvants, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (e.g. epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (e.g. silicone oils), preservatives, viscosity regulators, adhesives and / or tackifiers, fertilizers or other active ingredients for obtaining specific effects, such as bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0182] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, screening and / or compressing the solid active ingredient, and in the presence of at least one auxiliary, for example by intimately mixing and / or grinding the active ingredient with one or more auxiliary agents. These methods for preparing the compositions and the use of compound (I) for preparing these compositions are also subject matter of the present invention.

[0183] Another aspect of the invention relates to the use of a compound as defined in any one of embodiments 1 to 14, a composition comprising at least one compound as defined in any one of embodiments 1 to 14, or a fungicidal or insecticidal mixture comprising at least one compound as defined in any one of embodiments 1 to 14 (mixed with other fungicides or insecticides as described above) for controlling or preventing infestation of plants, such as plants (such as crop plants), their propagation materials (such as seeds), harvested crops (such as harvested food crops), or non-living materials by insects or phytopathogenic microorganisms, preferably fungal organisms.

[0184] Another aspect of the present invention relates to a method for controlling or preventing plants (e.g. plants (e.g. crop plants)), their propagation materials (e.g. seeds), harvested crops (e.g. harvested food crops), or non-living materials from being infested by phytopathogenic microorganisms or spoilage microorganisms or organisms potentially harmful to humans (especially fungal organisms), which method comprises applying a compound as defined in any one of Embodiments 1 to 14 as an active ingredient to these plants, parts of these plants or their loci, their propagation materials, or any parts of these non-living materials.

[0185] Control or prevention means the reduction of infestation by insects or phytopathogenic or spoilage microorganisms or organisms potentially harmful to humans, especially fungal organisms, to such a level that an improvement is demonstrated.

[0186] The preferred method of controlling or preventing crop plants from being infected by plant pathogenic microorganisms (especially fungal organisms) or insects is leaf application, which includes applying a compound as defined in any one of Examples 1 to 14 or an agrochemical composition containing at least one of the compounds. Frequency of application and application ratio will depend on the risk of infection by the corresponding pathogen or insect. However, the compound with formula (I) can also be applied to the soil (soil application) by roots (systemic action) by irrigating the place of plants with liquid formulations or by applying the compound in solid form, for example, in granular form to the soil. In rice crops, such granules can be applied to the paddy field of irrigation. The compound with formula (I) can also be applied to seeds (coating) by impregnating seeds or tubers with liquid formulations of fungicides or coating them with solid formulations.

[0187] The invention will now be illustrated by the following non-limiting examples.All references cited are incorporated by reference.

[0188] Examples

[0189]

[0190]

[0191]

[0192]

[0193] Biological Examples

[0194] experiment:

[0195] The fungus conidia from frozen storage is directly mixed in the nutrient broth (PDB potato dextrose broth). The DMSO solution of the test compound is placed in a microtiter plate (96 wells) and the nutrient broth comprising the fungus spore is added thereto. These test plates are hatched at 24°C and after 3-4 days, the inhibition of growth (to the control percentage of the multi-primary coryneform bacteria) is determined by photometry at 620nm. The activity of the compound is drawn by comparing the growth inhibition in the treated test solution with the growth in the untreated control solution (check). The concentration of the compound is 6.7, 2.2, 0.74, 0.25, 0.082 and 0.027ppm.

[0196] The following compounds gave at least 70% control of Corynespora polymyxinii at 6.7 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Examples 2, 4, 6, 9, 11, 12, 13, 16.

[0197] The compounds as defined in any one of Examples 1 to 14 can be distinguished from other compounds by a greater efficacy at low application rates, which can be verified by a person skilled in the art using the experimental procedures outlined in the above biological tests, using lower application rates (if necessary) such as 6ppm, 3ppm, 2.2ppm, 1.5ppm, 0.8ppm, 0.74ppm, 0.25ppm, 0.2ppm, 0.082ppm or 0.027ppm.

Claims

1. A method for controlling or preventing a plant from being infected by a plant pathogenic microorganism, the method comprising applying a fungicidal effective amount of a compound selected from the group consisting of: 、 、 、 、 ,and 。 2. The method according to claim 1, wherein the compound is selected from 、 、 、 、 、 、 、 、 、 、 ,and 。 3. The method according to claim 1 or claim 2, wherein the compound is the (R)-enantiomer.

4. The method according to claim 1 or claim 2, wherein the compound is the (S)-enantiomer.

5. The method of claim 1 or claim 2, wherein the plant is selected from beans, cucumbers, papayas, sweet potatoes and tomatoes.

6. The method according to claim 1 or claim 2, wherein the plant is selected from cowpea and soybean.

7. The method of claim 1 or claim 2, wherein the plant is soybean.

8. Use of a compound as defined in any one of claims 1 to 4 for controlling or preventing infection of plants by the phytopathogenic microorganism Corynespora polytomata.

9. The use according to claim 8, wherein the plant is selected from beans, cucumbers, papayas, sweet potatoes and tomatoes.

10. The use according to claim 8, wherein the plant is selected from cowpea and soybean.

11. The use according to claim 8, wherein the plant is soybean.

12. The method according to claim 5, wherein the compound is selected from 、 ,and 。 13. The method according to claim 12, wherein the plant is soybean.

14. The use according to claim 8, wherein the compound is selected from 、 ,and 。 15. The use according to claim 14, wherein the plant is soybean.

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