WO2010025870A1 - Synergistic combinations of thiadiazol carbonic acid derivatives - Google Patents

Synergistic combinations of thiadiazol carbonic acid derivatives Download PDF

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Publication number
WO2010025870A1
WO2010025870A1 PCT/EP2009/006202 EP2009006202W WO2010025870A1 WO 2010025870 A1 WO2010025870 A1 WO 2010025870A1 EP 2009006202 W EP2009006202 W EP 2009006202W WO 2010025870 A1 WO2010025870 A1 WO 2010025870A1
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Prior art keywords
cyclopropyl
thiadiazole
methyl
carboxamide
carboxylate
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PCT/EP2009/006202
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French (fr)
Inventor
Oswald Ort
Peter Dahmen
Daniela Portz
Uirike Wachendorff-Neumann
Tomoki Tsuchiya
Kerstin Ilg
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Bayer Cropscience Ag
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Publication of WO2010025870A1 publication Critical patent/WO2010025870A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention relates to active compound combinations, in particular within a pesticide composition, which comprises (A) a compound of formula (I) and other pesticides (B). Moreover, the invention relates to a method for curatively or preventively controlling the phytopathogenic fungi and/or pests and/or microorganisms of plants or crops, to the use of a combination according to the invention for the treatment of seed, to a method for protecting a seed and not at least to the treated seed.

Description

Synergistic combinations of thiadiazol carbonic acid derivatives
The invention relates to active compound combinations, in particular within a pesticide composition, which comprises (A) at least one compound of formula (I) and at least one further pesticidally active compound (B). Moreover, the invention relates to a method for curatively or preventively controlling the phytopathogenic fungi and/or pests and/or microorganisms of plants or crops, to the use of a combination according to the invention for the treatment of seed, to a method for protecting a seed and not at least to the treated seed.
The compounds according to formula (I) and the preparation thereof are disclosed in WO 2006/098128 sowie JP 2007-84566.
Since, moreover, the environmental and economic requirements imposed on modern-day pesticides are continually increasing, with regard, for example, to the spectrum of action, toxicity, selectivity, application rate, formation of residues, and favourable preparation ability, and since, furthermore, there may be problems, for example, with resistances, a constant task is to develop new pesticide agents which in some areas at least have advantages over their known counterparts.
The invention provides active compound combinations/compositions which in some aspects at least achieve the stated objectives.
It has now been found, surprisingly, that the combinations according to the invention not only bring about the additive enhancement of the spectrum of action with respect to the pathogen to be controlled that was in principle to be expected but achieves a synergistic effect which extends the range of action of the component (A) and of the component (B) in two ways. Firstly, the rates of application of the component (A) and of the component (B) are lowered whilst the action remains equally good. Secondly, the combination still achieves a high degree of pathogen control even where the two individual compounds have become totally ineffective in such a low application rate range. This allows, on the one hand, a substantial broadening of the spectrum of phytopathogens that can be controlled and, on the other hand, increased safety in use.
However, besides the actual synergistic action with respect to pesticidal activity, the pesticidal combinations according to the invention also have further surprising advantageous properties which can also be described, in a wider sense, as synergistic activity. Examples of such advantageous properties that may be mentioned are:
a broadening of the spectrum of pesticidal activity to other phytopathogens, for example to resistant strains; a reduction in the rate of application of the active ingredients; adequate pest control with the aid of the compositions according to the invention, even at a rate of application at which the individual compounds are totally ineffective;
advantageous behaviour during formulation or upon application, for example upon grinding, sieving, emulsifying, dissolving or dispensing; increased storage stability; improved stability to light; more advantageuos degradability; improved toxicological or ecotoxicological behaviour; improved characteristics of the useful plants including: emergence, crop yields, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf color, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigor, and early germination; or any other advantages familiar to a person skilled in the art.
The combination according to the invention can also provide an improved systemicity to the active compounds that are used. Indeed, even if some of the used pesticide compounds do not possess any or a satisfying systemicity, within the composition according to the invention these compounds can exhibit such a property.
In a similar manner, the combination according to the invention can allow an increased persistence of the pesticide efficacy of the active compounds that are employed.
Another advantage of the combination according to the invention relies in that an increased curativity is achievable.
Accordingly, the present invention provides a combination comprising:
(A) At least one 1,2,3-thiadiazole compound represented by formula (I)
Figure imgf000004_0001
(I) wherein R1 represents:
(a)
-C(=W')YR2
wherein R2 represents a hydrogen atom; (Ci-C2o)alkyl; halo(Ci-C20)alkyl; (C2-C2o)alkenyl; halo(C2- C20)alkenyl; (C2-C20)alkynyl; halo(C2-C20)alkynyl; (C3-C12)cycloalkyl; halo(C3-Ci2)cycloalkyl; (Cr C6)alkoxy(Ci-C6)alkyl; (C1-C6)alkylthio(C1-C6)alkyl; aryl(CrC6)alkyl which may be substituted on its ring with a substituent Z; aryloxy (Ci-C6)alkyl which may be substituted on its ring with a substituent Z; arylthio(CrC6)alkyl which may be substituted on its ring with a substituent Z; aryl which may be substituted with a substituent Z;
Figure imgf000005_0001
(Ci-C6)alkoxycarbonyl(Ci- C6)alkyl; carbamoyl(Ci-C6)alkyl; carbamoyl(Ci-C6)alkyl, having on the nitrogen atom 1 or 2 substituents which are the same or different and are selected from (Ci-Cio)alkyl, halo(Ci-Cio)alkyl, (C2-Cio)alkenyl, (C3-Ci0)cycloalkyl, phenyl which may be substituted with a substituent Z, or phenyl(Ci-C6) alkyl which may be substituted on its ring with a substituent Z; cyano(CrQ)alkyl; a heterocyclic ring which may be substituted with a substituent Z; heterocyclic (Ci-C6)alkyl which may be substituted on its ring with a substituent Z; (Ci-C2o)alkylcarbonyl; (C2- C20)alkynylcarbonyl; (C2-C6)alkenylcarbonyl; (C3-C6)cycloalkylcarbonyl; phenylcarbonyl which may be substituted with a substituent Z; heterocyclic carbonyl which may be substituted with a substituent Z; (Ci-C2o)alkylsulfonyl; halo(Ci-C2o)alkylsulfonyl; arylsulfonyl which may be substituted with a substituent Z; aryl(Ci-C6)alkylsulfonyl which may be substituted on its ring with a substituent Z;
-C(=W2)NR3R4
wherein R3 and R4 are the same or different and each represents a hydrogen atom, (Ci-Cio)alkyl, halo(Ci-Cio) alkyl, (C2-Ci0)alkenyl, (C3-Ci0)cycloalkyl, phenyl which may be substituted with a substituent Z, phenyl(Ci-C6)alkyl which may be substituted on its ring with a substituent Z, (Q- C6)alkoxy, phenoxy which may be substituted with a substituent Z or phenyl(Ci-C6)alkyloxy which may be substituted on its ring with a substituent Z, or R3 and R4 may be taken together to form (C2-C6)alkylene which may be interrupted by an oxygen atom, a sulfur atom or NR5 wherein R5 represents a hydrogen atom, (Ci-C6)alkyl or phenyl which may be substituted with a substituent Z, and W2 represents an oxygen atom or a sulfur atom; -SO2NR3R4 wherein R3 and R4 have the same meanings as defined above; or -N=C(R3)R4 wherein R3 and R4 have the same meanings as defined above, Y represents an oxygen atom; a sulfur atom; -N(R6)- wherein R6 represents a hydrogen atom, (Ci-C6)alkyl, (C3-C6)cycloalkyl, phenyl which may be substituted with a substituent Z, phenyl(Ci-C6)alkyl which may be substituted with a substituent Z, (Cj- - A -
Cio)alkylcarbonyl, (C2-C i0)alkynylcarbonyl, (C2-Ci0)alkenylcarbonyl, (C3-C6)cycloalkylcarbonyl, phenylcarbonyl which may be substituted with a substituent Z, or heterocyclic ring-carbonyl which may be substituted with a substituent Z; or -N(R6)O- wherein R6 has the same meaning as defined above,
and W1 represents an oxygen atom or a sulfur atom,
(b) a group represented by the following formula
Figure imgf000006_0001
wherein n represents an integer of from 0 to 4, and W3 and W4 are the same or different and each represents an oxygen atom or a sulfur atom,
or
(c) cyano;
wherein
Z' s are the same or different and each represents one or more substituents selected from a halogen atom; hydroxyl; cyano; nitro; (CrC6)alkyl; halo(CrC6)alkyl; (C3-Ci2)cycloalkyl; halo(Q- Ci2)cycloalkyl; phenyl which may be substituted with 1 to 5 substituents which are the same or different and are selected from a halogen atom, hydroxyl, cyano, nitro, (Q-C6)alkyl, halo(Q- C6)alkyl, (Q-C6)alkoxy, halo(Q-C6)alkoxy, (Q-C6)alkylthio, halo(CrC6)alkylthio, carboxyl, (C1- C6)alkoxycarbonyl, carbamoyl and substituted carbamoyl having a substituent(s) X which are the same or different on the nitrogen atom; phenyl(Q-C6)alkyl which may have on its ring from 1 to 5 substituents which are the same or different and are selected from a halogen atom, hydroxyl, cyano, nitro, (CrC6)alkyl, halo(CrC6)alkyl, (CrC6)alkoxy, halo(CrC6)alkoxy, (CrC6)alkylthio, halo(Q- C6)alkylthio, carboxyl, (Ci-C6)alkoxycarbonyl, carbamoyl and substituted carbamoyl having a substituent(s) X which are the same or different on the nitrogen atom; (CrC6)alkoxy; halo(Q- C6)alkoxy; (CrC6)alkylthio; halo(CrC6)alkylthio; (CrC6)alkylsulfinyl; halo(Ci-C6)alkylsulfinyl; (CrC6)alkylsulfonyl; halo(Q-C6)alkylsulfonyl; phenoxy which may have from 1 to 5 substituents which are the same or different and are selected from a halogen atom, hydroxyl, cyano, nitro, (Q- C6)alkyl, halo(Q-C6)alkyl, (Q-C6)alkoxy, halo(Q-C6)alkoxy, (Q-C6)alkylthio, halo(Q- C6)alkylthio, carboxyl, (Q-C6)alkoxycarbonyl, carbamoyl and substituted carbamoyl having a substituent(s) X which are the same or different on the nitrogen atom; phenylthio which may have from 1 to 5 substituents which are the same or different and are selected from a halogen atom, hydroxyl, cyano, nitro, (Ci-C6)alkyl, halo(Q-Q)alkyl, (Ci-C6)alkoxy, halo(Q-C6)alkoxy, (Q- C6)alkylthio, halo(Ci-Q)alkylthio, carboxyl, (Q-C6)alkoxycarbonyl, carbamoyl and substituted carbamoyl having a substituent(s) X on the nitrogen atom; phenylsulfϊnyl which may have from 1 to 5 substituents which are the same or different and are selected from a halogen atom, hydroxyl, cyano, nitro, (CrC6)alkyl, halo(CrC6)alkyl, (CrC6)alkoxy, halo(CrC6)alkoxy, (CrC6)alkylthio, halo (Ci-C6)alkylthio, carboxyl, (Q-C6)alkoxycarbonyl, carbamoyl and substituted carbamoyl having a substituent(s) X on the nitrogen atom; phenylsulfonyl which may have from 1 to 5 substituents which are the same or different and are selected from a halogen atom, hydroxyl, cyano, nitro, (CrC6)alkyl, halo(d-C6)alkyl, (Ci-C6)alkoxy, halo(CrC6)alkoxy, (CrC6)alkylthio, halo(CrC6)alkylthio, carboxyl, (Q-C6)alkoxycarbonyl, carbamoyl and substituted carbamoyl having a substituent(s) X on the nitrogen atom; phenyl(Ci-C6)alkyloxy which may have on its ring from 1 to 5 substituents which are the same or different and are selected from a halogen atom, hydroxyl, cyano, nitro, (CrC6)alkyl, halo(CrC6)alkyl, (Q-C6)alkoxy, halo(CrC6)alkoxy, (Q- C6)alkylthio, halo(Ci-C6)alkylthio, carboxyl, (Ci-C6)alkoxycarbonyl, carbamoyl and substituted carbamoyl having a substituent(s) X on the nitrogen atom; carboxyl; (Ci-C6)alkoxycarbonyl; carbamoyl which may be substituted with a substituent(s) X; (Ci-C6)alkylcarbonyl or phenylcarbonyl which may have from 1 to 5 substituents which are the same or different and are selected from a halogen atom, hydroxyl, cyano, nitro, (Q-C6)alkyl, halo(Ci-C6)alkyl, (Q- C6)alkoxy, halo(CrC6)alkoxy, (CrC6)alkylthio, halo(CrC6)alkylthio, carboxyl, (Q- C6)alkoxycarbonyl, carbamoyl and substituted carbamoyl having a substituent(s) X on the nitrogen atom;
X represents (Q-Qo)alkyl; halo(Q-Q0)alkyl; phenyl which may have from 1 to 5 substituents which are the same or different and are selected from a halogen atom, cyano, nitro, (Q-C6)alkyl, halo(Q-C6)alkyl, (Q-C6)alkoxy, halo(Q-C6)alkoxy, (Q-C6)alkylthio or halo(Q-C6)alkylthio; or phenyl(Q-C6)alkyl which may have on its ring from 1 to 5 substituents which are the same or different and are selected from a halogen atom, cyano, nitro, (Q-C6)alkyl, halo(Q-C6)alkyl, (Q- C6)alkoxy, halo(Q-C6)alkoxy, (Q-C6)alkylthio or halo(Q-C6)Alkylthio;
and
(B) at least one further active compound selected from the group consisting of
(B-I) Inhibitors of the nucleic acid synthesis, for example benalaxyl, benalaxyl-M, bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M, ofurace, oxadixyl and oxolinic acid. (B-2) Inhibitors of the mitosis and cell division, for example benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fuberidazole, pencycuron, thiabendazole, thiophanate, thiophanate-methyl and zoxamide.
(B-3) Inhibitors of the respiration, for example diflumetorim as CI-respiration inhibitor; bixafen, boscalid, carboxin, fenfuram, flutolanil, fluopyram, furametpyr, furmecyclox, isopyrazam (9R-component), isopyrazam (9S- component), mepronil, oxycarboxin, penthiopyrad, thifluzamide as CII- respiration inhibitor; amisulbrom, azoxystrobin, cyazofamid, dimoxystrobin, enestroburin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyribencarb, trifloxystrobin as CHI-respiration inhibitor.
(B-4) Compounds capable to act as an uncoupler, like for example binapacryl, dinocap, fluazinam and meptyldinocap.
(B-5) Inhibitors of the ATP production, for example fentin acetate, fentin chloride, fentin hydroxide, and silthiofam.
(B-6) Inhibitors of the amino acid and/or protein biosynthesis, for example andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim and pyrimethanil.
(B-7) mhibitors of the signal transduction, for example fenpiclonil, fludioxonil and quinoxyfen.
(B-8) Inhibitors of the lipid and membrane synthesis, for example biphenyl, chlozolinate, edifenphos, etridiazole, iodocarb, iprobenfos, iprodione, isoprothiolane, procymidone, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-methyl and vinclozolin.
(B-9) Inhibitors of the ergosterol biosynthesis, for example aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemoφh acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol, pefurazoate, penconazole, piperalin, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon, triadimenol, tridemoφh, triflumizole, triforine, triticonazole, uniconazole, viniconazole and voriconazole.
(B- 10) Inhibitors of the cell wall synthesis, for example benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins, polyoxorim, prothiocarb, validamycin A, and valiphenal.
(B-I l) Inhibitors of the melanine biosynthesis, for example carpropamid, diclocymet, fenoxanil, phthalide, pyroquilon and tricyclazole.
(B-12) Compounds capable to induce a host defence, like for example acibenzolar-S- methyl, probenazole, and tiadinil.
(B-13) Compounds capable to have a multisite action, like for example bordeaux mixture, captafol, captan, chlorothalonil, copper naphthenate, copper oxide, copper oxychloride, copper preparations such as copper hydroxide, copper sulphate, dichlofluanid, dithianon, dodine, dodine free base, ferbam, fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper, propamidine, propineb, sulphur and sulphur preparations including calcium polysulphide, thiram, tolylfluanid, zineb and ziram.
(B-14) Further compounds like for example 2,3-dibutyl-6-chlorothieno[2,3- d]pyrimidin-4(3H)-one, ethyl (2Z)-3-amino-2-cyano-3-phenylprop-2-enoate, N- [2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4- carboxamide, N- {2-[ 1 , 1 '-bi(cyclopropyl)-2-yl]phenyl} -3 -(difluoromethyl)- 1 - methyl- lH-pyrazole-4-carboxamide, 3 -(difluoromethyl)- 1 -methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)- 1 H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-[4- fluoro-2-( 1 , 1 ,2,3,3 ,3-hexafluoropropoxy)phenyl]- 1 -methyl- 1 H-pyrazole-4- carboxamide, (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4- yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide, (2E)-2- {2- [( {[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2- ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide, 2-chloro-N-( 1 , 1 ,3 -trimethy 1-2,3 -dihydro- 1 H-inden-4-yl)pyridine-3 - carboxamide, N-(3 -ethyl-3 ,5 ,5 -trimethylcyclohexyl)-3 -(formylamino)-2- hydroxybenzamide, 5-methoxy-2-methyl-4-(2-{[({(lE)-l-[3-
(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro- 3H-l,2,4-triazol-3-one, (2E)-2-(methoxyimmo)-N-methyl-2-(2-{[({(lE)-l-[3- (trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide, (2E)-2-(methoxyimino)-N-methyl-2- {2-[(E)-( { 1 -[3 -
(trifluoromethyl)phenyl]ethoxy} imino)methyl]phenyl} ethanamide, (2E)-2- {2- [({[(lE)-l-(3-{[(E)-l-fluoro-2- phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2- (methoxyimino)-N-methylethanamide, 1 -(4-chlorophenyl)-2-( IH-1 ,2,4-triazol- l-yl)cycloheptanol, methyl l-(2,2-dimethyl-2,3-dihydro-lH-inden-l-yl)-lH- imidazole-5-carboxylate, N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)- 4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide, N'-{5-(difluoromethyl)- 2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N- methylimidoformamide, O- { 1 -[(4-methoxyphenoxy)methyl]-2,2- dimethylpropyl} lH-imidazole-1-carbothioate, N-[2-(4-{[3-(4- chlorophenyl)prop-2-yn-l -yl]oxy} -3-methoxyphenyl)ethyl]-N2- (methylsulfonyl)valinamide, 5-chloro-7-(4-methylpiperidin- 1 -yl)-6-(2,4,6- trifluorophenyl)[l ,2,4]triazolo[ 1 ,5-a]pyrimidine, 5-amino-l ,3,4-thiadiazole-2- thiol, propamocarb-fosetyl, 1 -[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl 1 H-imidazole- 1 -carboxylate, 1 -methyl-N-[2-( 1 , 1 ,2,2-tetrafluoroethoxy)phenyl]-
3-(trifluoromethyl)-lH-pyrazole-4-carboxamide, 2,3,5,6-tetrachloro-4-
(methylsulfonyl)pyridine, 2-butoxy-6-iodo-3 -propyl -4H-chromen-4-one, 2- phenylphenol and salts, 3-(difluoromethyl)-l-methyl-N-[2-(l, 1,2,2- tetrafluoroethoxy)phenyl]-lH-pyrazole-4-carboxamide, 3,4,5-trichloropyridine- 2,6-dicarbonitrile, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3- yl]pyridine, 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6- methylpyridazine, 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6- dimethylpyridazine, quinolin-8-ol, quinolin-8-ol sulfate (2:1) (salt), 5-methyl-6- octyl-3,7-dihydro[l,2,4]triazolo[l,5-a]pyrimidin-7-amine, 5-ethyl-6-octyl-3,7- dihydro[l,2,4]triazolo[l,5-a]pyrimidin-7-amine, benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, chloroneb, cufiraneb, cyflufenamid, cymoxanil, cyprosulfamide, dazomet, debacarb, dichlorophen, diclomezine, dicloran, difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomate, ferimzone, flumetover, fluopicolide, fluoroimide, flusulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin, isotianil, methasulfocarb, methyl (2E)-2-{2-[({cyclopropyl[(4- methoxyphenyl)imino]methyl } thio)methyl]phenyl } -3 -methoxyacrylate, methyl isothiocyanate, metrafenone, (5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4- trimethoxy-6-methylphenyl)methanone, mildiomycin, tolnifanide, N-(4- chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-l-yloxy)phenyl]propanamide, N-[(4- chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-l - yloxy)phenyl]propanamide, N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4- dichloropyridine-3-carboxamide, N-[ 1 -(5-bromo-3-chloropyridin-2-yl)ethyl]- 2,4-dichloropyridine-3-carboxamide, N-[l-(5-bromo-3-chloropyridin-2- yl)ethyl]-2-fluoro-4-iodopyridine-3 -carboxamide, N- ((Z)- [(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3- difluorophenyl]methyl} -2-phenylacetamide, N- ((E)-
[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3- difluorophenyl]methyl} -2-phenylacetamide, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts, phenazine-1-carboxylic acid, phenothrin, phosphorous acid and its salts, propamocarb fosetylate, propanosine-sodium, proquinazid, pyrrolnitrine, quintozene, S-prop-2-en-l-yl 5-amino-2-(l-methylethyl)-4-(2-methylphenyl)-3-oxo-2,3-dihydro-lH- pyrazole-1-carbothioate, tecloftalam, tecnazene, triazoxide, trichlamide, 5- chloro-N'-phenyl-N'-prop-2-yn-l -ylthiophene-2-sulfonohydrazide and zarilamid;
(B- 15) Acetylcholinesterase (AChE) inhibitors, for example
carbamates, e.g. alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam- sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, and xylylcarb; or
organophosphates, e.g. acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chloφyrifos
(-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphon, dialifos, diazinon, dichlofenthion, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formo- thion, fosmethilan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl, O-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/
-ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion, and imicyafos.
(B- 16) GABA-gated chloride channel antagonists, for example
organochlorines, e.g. camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, and methoxychlor; or
fiproles (phenylpyrazoles), e.g. acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, and vaniliprole.
(B- 17) Sodium channel modulators/voltage-dependent sodium channel blockers, for example
pyrethroids, e.g. acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin
(alpha-, beta-, theta-, zeta-), cyphenothrin, deltamethrin, empenthrin (IR isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin (IR trans isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau- fluvalinate, tefluthrin, terallethrin, tetramethrin (-1R- isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum), eflusilanat;
DDT; or methoxychlor.
(B-18) Nicotinergic acetylcholine receptor agonists/antagonists, for example chloronicotinyls, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, imidaclothiz, nitenpyram, nithiazine, thiacloprid, thiamethoxam, AKD- 1022,
nicotine, bensultap, cartap, thiosultap-sodium, and thiocylam.
(B- 19) Allosteric acetylcholine receptor modulators (agonists), for example
spinosyns, e.g. spinosad and spinetoram.
(6) Chloride channel activators, for example
mectins/macrolides, e.g. abamectin, emamectin, emamectin benzoate, ivermectin, lepimectin, and milbemectin; or
juvenile hormone analogues, e.g. hydroprene, kinoprene, methoprene, epofenonane, triprene, fenoxycarb, pyriproxifen, and diofenolan.
(B-20) Active ingredients with unknown or non-specific mechanisms of action, for example
gassing agents, e.g. methyl bromide, chloropicrin and sulfuryl fluoride;
selective antifeedants, e.g. cryolite, pymetrozine, pyrifluquinazon and flonicamid; or
mite growth inhibitors, e.g. clofentezine, hexythiazox, etoxazole.
(B-21) Oxidative phosphorylation inhibitors, ATP disruptors, for example
diafenthiuron;
organotin compounds, e.g. azocyclotin, cyhexatin and fenbutatin oxide; or
propargite, tetradifon.
(B-22) Oxidative phoshorylation decouplers acting by interrupting the H proton gradient, for example chlorfenapyr, binapacryl, dinobuton, dinocap and DNOC.
(B-23) Microbial disruptors of the insect gut membrane, for example Bacillus thuringiensis strains.
(B-24) Chitin biosynthesis inhibitors, for example benzoylureas, e.g. bistrifluron, chlorfluazuron, difiubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron or triflumuron.
(B-25) Buprofezin.
(B-26) Moulting disruptors, for example cyromazine.
(B-27) Ecdysone agonists/disruptors, for example
diacylhydrazines, e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide, and Fufenozide (JSl 18); or
azadirachtin.
(B-27) Octopaminergic agonists, for example amitraz.
(B-28) Site EI electron transport inhibitors/site II electron transport inhibitors, for example hydramethylnon; acequinocyl; fluacrypyrim; or cyflumetofen and cyenopyrafen.
(B-29) Electron transport inhibitors, for example
Site I electron transport inhibitors, from the group of the METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, and rotenone; or
voltage-dependent sodium channel blockers, e.g. indoxacarb and metaflumizone.
(B-30) Fatty acid biosynthesis inhibitors, for example tetronic acid derivatives, e.g. spirodiclofen and spiromesifen; or
tetramic acid derivatives, e.g. spirotetramat.
(B-31) Neuronal inhibitors with unknown mechanism of action, e.g. bifenazate.
(B-32) Ryanodine receptor effectors, for example diamides, e.g. flubendiamide,
(R)1(S)-S-ChIOr0-N1 - {2-methyl-4-[ 1 ,2,2,2-tetrafluoro- 1 - (trifluoromethyl)ethyl]phenyl} -N2 -(I -methyl -2 -methylsulphonyl- ethyl)phthalamide, chlorantraniliprole (Rynaxypyr), or Cyantraniliprole (Cyazypyr). (B-33) Further active ingredients with unknown mechanism of action, for example amidoflumet, fenamiphos, aldicarb, ethoprofos, oxamyl, benclothiaz, benzoximate, bromopropylate, buprofezin, chinomethionat, chlordimeform, chlorobenzilate, clothiazoben, cycloprene, dicofol, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure, japonilure, metoxadiazone, petroleum, potassium oleate, pyridalyl, sulfluramid, tetrasul, triarathene or verbutine; or one of the following known active compounds
4- { [(6-brompyrid-3 -yl)methyl] (2-fluorethyl)amino } furan-2(5H)-on (known from WO 2007/115644), 4-{[(6-fluorpyrid-3-yl)methyl](2,2- difluorethyl)amino}furan-2(5H)-on (known from WO 2007/115644), 4-{[(2- chlor-l,3-thiazol-5-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (known from WO 2007/115644), 4-{[(6-cmorpyrid-3-yl)methyl](2- fluorethyl)amino}furan-2(5H)-on (known from WO 2007/ 115644), 4- {[(6- chlθφyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on known from WO 2007/115644), 4-{[(6-chlor-5-fluorpyrid-3- yl)methyl](methyl)amino}furan-2(5H)-on (known from WO 2007/115643), 4- {[(5,6-dichloφyrid-3-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (known from WO 2007/115646), 4-{[(6-chlor-5-fluorpyrid-3- yl)methyl](cyclopropyl)amino}furan-2(5H)-on (known from WO 2007/115643), 4-{[(6-chloφyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)- on (known from EP-A-O 539 588), 4-{[(6-chlθφyrid-3- yl)methyl](methyl)amino}furan-2(5H)-on (known from EP-A-O 539 588), [(6- chlθφyridin-3-yl)methyl](methyl)oxido-λ4-sulfanylidencyanamid (known from WO 2007/149134), [l-(6-chloφyridin-3-yl)ethyl](methyl)oxido-λ4- sulfanylidencyanamid (known from WO 2007/149134) and its diastereomeres
(A) and (B)
Figure imgf000015_0001
(A) (B)
(also known from WO 2007/149134), [(6-trifluormethylpyridin-3-yl)methyl](methyl)oxido-λ4- sulfanylidencyanamid (known from WO 2007/095229), or [l-(6-trifluormethylpyridin-3- yl)ethyl](methyl)oxido-λ4-sulfanylidencyanamid (known from WO 2007/149134) and its diastereomeres (C) and (D), namely Sulfoxaflor
Figure imgf000016_0001
(C) (D).
(also known from WO 2007/149134).
Preference is given to combinations comprising compounds of the formula (T), wherein R1 represents -C(=W1)YR2, wherein R2 represents (C3-C io)alkyl or substituted phenyl(Ci-C6)alkyl having on its ring one or more substituents which are the same or different and are selected from a halogen atom, cyano, (Ci-C6)alkyl, halo(Ci-C6)alkyl, (CrC6) alkoxy, halo(Ci-C6)alkoxy and (Q- C6)alkoxycarbonyl, and W1 and Y represent an oxygen atom, or a salt thereof.
Preference is given to combinations comprising compounds of the formula (I), wherein R1 represents -C(=W')YR2, wherein R2 represents (C3-Ci0)alkyl or substituted phenyl(Ci-C6)alkyl having on its ring one or more substituents which are the same or different and are selected from a halogen atom, cyano, (Ci-C6)alkyl, halo(Ci-C6)alkyl, (Ci-C6) alkoxy, halo(Ci-C6)alkoxy and (Cr C6)alkoxycarbonyl, and W1 and Y represent an oxygen atom, or a salt thereof.
Preference is given to combinations comprising compounds of the formula (I), wherein R1 represents -C(=W1)YR2, wherein R2 represents (CrC6)alkyl; substituted phenyl(CrC6)alkyl having on its ring one or more substituents which are the same or different and are selected from a halogen atom, cyano, (CrC6)alkyl, halo(CrC6)alkyl, (d-C6)alkoxy, halo(Ci-C6)alkoxy and (Ci- C6)alkoxycarbonyl; substituted phenyl having one or more substituents which are the same or different and are selected from a halogen atom, cyano, methyl, ethyl, n-propyl, n-butyl, t-butyl, halo(Ci-C6)alkyl, methoxy, ethoxy, halo(CrC6)alkoxy and (Ci-C6)alkoxycarbonyl; thiazolyl; substituted thiazolyl having one or more substituents which are the same or different and are selected from a halogen atom, cyano, (C'-C6)alkyl, halo(Ci-C6)alkyl, (Ci-C6)alkoxy, halo(Cr C6)alkoxy and phenyl; benzothiazolyl; substituted benzothiazolyl having one or more substituents which are the same or different and are selected from a halogen atom, cyano, (Cp C6)alkyl, halo(Ci-C6)alkyl, (CrC6)alkoxy, halo(CrC6)alkoxy and phenyl; pyrimidyl; substituted pyrimidyl having one or more substituents which are the same or different and are selected from a halogen atom, cyano, (Ci-C6) alkyl, halo(CrC6)alkyl, (CrC6)alkoxy, halo(CrC6)alkoxy and phenyl; phenylsulfonyl; or phenylsulfonyl having one or more substituents which are the same or different and are selected from a halogen atom, cyano, (CrC6)alkyl, halo(Ci-C6)alkyl, (Cr C6)alkoxy, halo(d-C6)alkoxy and phenyl,
W1 represents an oxygen atom, and Y represents -NH-, or a salt thereof.
Particularly preferred are combinations wherein the compound of formula (I) is selected from the group consisting of:
(A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate,
(A-2) (2-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate,
(A-3) (3-chlorobenzyl) 4-cyclopropyl-l ,2,3-thiadiazole-5-carboxylate,
(A-4) (4-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate,
(A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l ,2,3-thiadiazole-5-carboxylate,
(A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate,
(A-7) N-benzyl -4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide,
(A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide,
(A-9) 3 ' -chloro^-cyclopropyM ' -methyl- 1 ,2,3 -thiadiazole-5 -carboxanilide,
(A- 10) 4-cyclopropyl-2 ' ,4 ' -dimethoxy- 1,2,3 -thiadiazole-5 -carboxanilide,
(A- 11) 4-cyclopropyl-3 ' ,4 ' -dimethoxy- 1 ,2,3 -thiadiazole-5 -carboxanilide,
(A-12) 2'-carboxy-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxanilide,
(A- 13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl- 1 ,2,3 -thiadiazole-5 -carboxamide,
(A-14) N-phenylsulfonyl-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide,
(A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l ,2,3 -thiadiazole-5 -carboxamide,
(A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide,
(A-17) 2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, or a salt thereof. Preference is further given to combinations comprising compound (B) selected from the list consisting of bixafen, boscalid, isopyrazam (9R-component), isopyrazam (9S-component), sedaxane (trans-isomer), sedaxane (cis-isomer), sedaxane (mixture of cis-/trans-isomers 0- 20%: 100-80%), penthiopyrad, azoxystrobin, fluoxastrobin, kresoxim-methyl, picoxystrobin, pyraclostrobin, trifloxystrobin, quinoxyfen, epoxiconazole, fenpropidin, fenpropimorph, fluquinconazole, prochloraz, propiconazole, prothioconazole, spiroxamine, tebuconazole, metrafenone.
Particularly preferred combinations are listed below:
(A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and bixafen; (A-I) octyl 4- cyclopropyl-l^^-thiadiazole-S-carboxylate, and boscalid; (A-I) octyl 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and isopyrazam (9R-component); (A-I) octyl 4-cyclopropyl- 1,2,3- thiadiazole-5-carboxylate, and isopyrazam (9S-component); (A-I) octyl 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and sedaxane (trans-isomer); (A-I) octyl 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and sedaxane (cis-isomer); (A-I) octyl 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and penthiopyrad;(A-l) octyl 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and azoxystrobin;(A-l) octyl 4-cyclopropyl- 1,2,3- thiadiazole-5-carboxylate, and fluoxastrobin; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and kresoxim-methyl; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and picoxystrobin; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and pyraclostrobin; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and trifloxystrobin; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and quinoxyfen; (A-I) octyl 4- cyclopropyl- 1,2,3 -thiadiazole-5-carboxylate, and epoxiconazole; (A-I) octyl 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and fenpropidin; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and fenpropimorph; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fluquinconazole; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and prochloraz; (A- 1) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and propiconazole; (A-I) octyl 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and prothioconazole; (A-I) octyl 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and prothioconazole; (A-I) octyl 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and spiroxamine; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and tebuconazole; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and metrafenone;
(A-2) (2-chlorobenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and bixafen; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and boscalid; (A-2) (2- chlorobenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and isopyrazam (9R-component); (A-2) (2-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and isopyrazam (9S- component); (A-2) (2-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and sedaxane (trans-isomer); (A-2) (2-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and sedaxane (cis-isomer); (A-2) (2-chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5- carboxylate, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-tbiadiazole-5-carboxylate, and penthiopyrad; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and azoxystrobin; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fluoxastrobin; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and kresoxim-methyl; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and picoxystrobin; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and pyraclostrobin; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and trifloxystrobin; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and quinoxyfen; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3 -thiadiazole-5 -carboxylate, and epoxiconazole; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and fenpropidin; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and fenpropimorph; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and fluquinconazole; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and prochloraz; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and propiconazole; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and prothioconazole; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and prothioconazole; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and spiroxamine; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3 -thiadiazole-5 -carboxylate, and tebuconazole; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l, 2,3 -thiadiazole-5-carboxylate, and metrafenone;
(A-3) (3 -chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and bixafen; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l, 2,3 -thiadiazole-5 -carboxylate, and boscalid; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and isopyrazam (9R-component); (A-3) (3-chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and isopyrazam (9S- component); (A-3) (3-chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and sedaxane (trans-isomer); (A-3) (3-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and sedaxane (cis-isomer); (A-3) (3-chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5- carboxylate, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-3) (3- chlorobenzyl) 4-cyclopropyl-l, 2,3 -thiadiazole-5-carboxylate, and penthiopyrad; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and azoxystrobin; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and fluoxastrobin; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and kresoxim-methyl; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and picoxystrobin; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and pyraclostrobin; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and trifloxystrobin; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and quinoxyfen; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and epoxiconazole; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenpropidin; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenpropimoφh; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fluquinconazole; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and prochloraz; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and propiconazole; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and prothioconazole; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and prothioconazole; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and spiroxamine; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and tebuconazole; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l ,2,3-thiadiazole-5-carboxylate, and metrafenone;
(A-4) (4-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and bixafen; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and boscalid; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and isopyrazam (9R-component); (A-4) (4-chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and isopyrazam (9S- component); (A-4) (4-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and sedaxane (trans-isomer); (A-4) (4-chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and sedaxane (cis-isomer); (A-4) (4-chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5- carboxylate, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3 -thiadiazole-5-carboxylate, and penthiopyrad; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and azoxystrobin; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fluoxastrobin; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and kresoxim-methyl; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and picoxystrobin; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3-tbiadiazole-5-carboxylate, and pyraclostrobin; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and trifloxystrobin; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and quinoxyfen; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and epoxiconazole; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3 -thiadiazole-5-carboxylate, and fenpropidin; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and fenpropimoφh; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2, 3 -thiadiazole-5-carboxylate, and fluquinconazole; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l, 2,3-thiadiazole-5-carboxylate, and prochloraz; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and propiconazole; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and prothioconazole; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and prothioconazole; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and spiroxamine; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and tebuconazole; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and metrafenone;
(A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and bixafen; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and boscalid; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and isopyrazam (9R-component); (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole- 5-carboxylate, and isopyrazam (9S-component); (A-5) (4-chloro-α-methylbenzyl) 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and sedaxane (trans-isomer); (A-5) (4-chloro-α- methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and sedaxane (cis-isomer); (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-5) (4-chloro-α-methylbenzyl) 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and penthiopyrad; (A-5) (4-chloro-α- methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and azoxystrobin; (A-5) (4- chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fluoxastrobin; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and kresoxim- methyl; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and picoxystrobin; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and pyraclostrobin; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and trifloxystrobin; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and quinoxyfen; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and epoxiconazole; (A-5) (4-chloro-α-methylbenzyl) 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenpropidin; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenpropimorph; (A-5) (4-chloro-α- methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fluquinconazole; (A-5) (4- chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and prochloraz; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and propiconazole; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and prothioconazole; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and prothioconazole; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and spiroxamine; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and tebuconazole; (A-5) (4-chloro-α-methylbenzyl) 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and metrafenone; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and bixafen; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-tbiadiazole-5-carboxylate, and boscalid; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and isopyrazam (9R-component); (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and isopyrazam (9S-component); (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and sedaxane (trans-isomer); (A-6) (4- methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and sedaxane (cis- isomer); (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-6) (4-methoxycarbonylbenzyl) 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and penthiopyrad; (A-6) (4- methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and azoxystrobin; (A- 6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fluoxastrobin; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and kresoxim-methyl; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and picoxystrobin; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and pyraclostrobin; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and trifloxystrobin; (A-6) (4-methoxycarbonylbenzyl) 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and quinoxyfen; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and epoxiconazole; (A-6) (4- methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenpropidin; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenpropimorph; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fluquinconazole; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and prochloraz; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl- 1,2,3-thiadiazole- 5 -carboxylate, and propiconazole; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl- 1,2,3 - thiadiazole-5-carboxylate, and prothioconazole; (A-6) (4-methoxycarbonylbenzyl) 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and prothioconazole; (A-6) (4- methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and spiroxamine; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl- 1,2,3 -thiadiazole-5-carboxylate, and tebuconazole; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and metrafenone;
(A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and bixafen; (A-7) N-benzyl-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and boscalid; (A-7) N-benzyl-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and isopyrazam (9R-component); (A-7) N-benzyl-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and isopyrazam (9S-component); (A-7) N- benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and sedaxane (trans-isomer); (A-7) N- benzyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and sedaxane (cis-isomer); (A-7) N- benzyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and sedaxane (mixture of cis-/trans- isomers 0-20%: 100-80%); (A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and penthiopyrad; (A-7) N-benzyM-cyclopropyl-l^S-thiadiazole-S-carboxamide, and azoxystrobin; (A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and fluoxastrobin; (A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and kresoxim- methyl; (A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and picoxystrobin; (A- 7) N-benzyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and pyraclostrobin; (A-7) N- beiizyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and trifloxystrobin; (A-7) N-benzyl-4- cyclopropyl-l^^-thiadiazole-S-carboxamide, and quinoxyfen; (A-7) N-benzyl-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and epoxiconazole; (A-7) N-benzyl-4-cyclopropyl-l,2,3- thiadiazole-5-carboxamide, and fenpropidin; (A-7) N-benzyl-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and fenpropimorph; (A-7) N-benzyl-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and fluquinconazole; (A-7) N-benzyl-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and prochloraz; (A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and propiconazole; (A-7) N-benzyM-cyclopropyl-l^jS-thiadiazole-S-carboxamide, and prothioconazole; (A-7) N-benzyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and prothioconazole; (A-7) N-benzyM-cyclopropyl-l^^-tbiadiazole-S-carboxamide, and spiroxamine; (A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and tebuconazole; (A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and metrafenone;
(A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and bixafen; (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and boscalid; (A-8) N-(4-t- butylbenzy^^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and isopyrazam (9R-component); (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and isopyrazam (PS- component); (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and sedaxane (trans-isomer); (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and sedaxane (cis-isomer); (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A- 8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and penthiopyrad; (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and azoxystrobin; (A-8) N- (4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fluoxastrobin; (A-8) N- (4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and kresoxim-methyl; (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and picoxystrobin; (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and pyraclostrobin; (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and trifloxystrobin; (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and quinoxyfen; (A-8) N- (4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and epoxiconazole; (A-8) N- (4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fenpropidin; (A-8) N-(4- t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fenpropimorph; (A-8) N-(4- t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fluquinconazole; (A-8) N- (4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and prochloraz; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and propiconazole; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and protbioconazole; (A-8) N-(4- t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and prothioconazole; (A-8) N- (4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spiroxamine; (A-8) N-(4- t-butylbenzyl^-cyclopropyl-l^^-truadiazole-S-carboxamide, and tebuconazole; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and metrafenone;
(A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and bixafen; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and boscalid; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and isopyrazam (9R- component); (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and isopyrazam (9S-component); (A-9) S'-chloro^-cyclopropyW-methyl-l^jS-thiadiazole-S- carboxanilide, and sedaxane (trans-isomer); (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3- thiadiazole-5-carboxanilide, and sedaxane (cis-isomer); (A-9) S'-chloro^-cyclopropyW- methyl-l,2,3-thiadiazole-5-carboxanilide, and sedaxane (mixture of cis-/trans-isomers 0- 20%:100-80%); (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and penthiopyrad; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and azoxystrobin; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and fluoxastrobin; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and kresoxim-methyl; (A-9) S'-chloro^-cyclopropyW-methyl-l^^-thiadiazole-S- carboxanilide, and picoxystrobin; (A-9) S'-chloro^-cyclopropyW-methyl-l^^-thiadiazole-S- carboxanilide, and pyraclostrobin; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5- carboxanilide, and trifloxystrobin; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5- carboxanilide, and quinoxyfen; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5- carboxanilide, and epoxiconazole; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5- carboxanilide, and fenpropidin; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5- carboxanilide, and fenpropimoφh; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole- 5 -carboxanilide, and fluquinconazole; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3- thiadiazole-5 -carboxanilide, and prochloraz; (A-9) 3'-chloro-4-cyclopropyl-4'-metbyl-l,2,3- thiadiazole-5 -carboxanilide, and propiconazole; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3- thiadiazole-5 -carboxanilide, and prothioconazole; (A-9) 3 '-chloro^-cyclopropyW -methyl- l,2,3-thiadiazole-5-carboxanilide, and prothioconazole; (A-9) 3'-chloro-4-cyclopropyl-4'- methyl-l,2,3-thiadiazole-5-carboxanilide, and spiroxamine; (A-9) S'-chloro^-cyclopropyW- methyl-l,2,3-thiadiazole-5-carboxanilide, and tebuconazole; (A-9) S'-chloro^-cyclopropyW- methyl-l,2,3-thiadiazole-5-carboxanilide, and metrafenone;
(A-IO) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and bixafen; (A-10) 4- cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and boscalid; (A-10) 4- cyclopropyl-2\4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and isopyrazam (9R- component); (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and isopyrazam (9S-component); (A-IO) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5- carboxanilide, and sedaxane (trans-isomer); (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3- thiadiazole-5-carboxanilide, and sedaxane (cis-isomer); (A-10) 4-cyclopropyl-2',4'-dimethoxy- l,2,3-thiadiazole-5-carboxanilide, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100- 80%); (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and penthiopyrad; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and azoxystrobin; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fluoxastrobin; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and kresoxim-methyl; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and picoxystrobin; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and pyraclostrobin; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and trifloxystrobin; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and quinoxyfen; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and epoxiconazole; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fenpropidin; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fenpropimoφh; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fluquinconazole; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and prochloraz; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and propiconazole; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and prothioconazole; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and prothioconazole; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and spiroxamine; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and tebuconazole; (A-10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and metrafenone;
(A-11) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and bixafen; (A-11) 4- cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and boscalid; (A-I l) 4- cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and isopyrazam (9R- component); (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and isopyrazam (9S-component); (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5- carboxanilide, and sedaxane (trans-isomer); (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3- thiadiazole-5-carboxanilide, and sedaxane (cis-isomer); (A-I l) 4-cyclopropyl-3',4'-dimethoxy- l,2,3-thiadiazole-5-carboxanilide, and sedaxane (mixture of cis-/trans-isomers 0-20%:100- 80%); (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and penthiopyrad; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and azoxystrobin; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fluoxastrobin; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and kresoxim-methyl; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and picoxystrobin; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and pyraclostrobin; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and trifloxystrobin; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and quinoxyfen; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and epoxiconazole; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fenpropidin; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fenpropimoφh; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fluquinconazole; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and prochloraz; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and propiconazole; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and prothioconazole; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and prothioconazole; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and spiroxamine; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-tbiadiazole-5-carboxanilide, and tebuconazole; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and metrafenone;
(A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and bixafen; (A-12) T- carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and boscalid; (A-12) 2'-carboxy-4- cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and isopyrazam (9R-component); (A-12) 2'- carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and isopyrazam (9S-component); (A- 12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and sedaxane (trans-isomer); (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and sedaxane (cis-isomer); (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and penthiopyrad; (A-12) 2'-carboxy~4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and azoxystrobin; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and fluoxastrobin; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and kresoxim-methyl; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and picoxystrobin; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and pyraclostrobin; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and trifloxystrobin; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and quinoxyfen; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and epoxiconazole; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and fenpropidin; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and fenpropimoφh; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and fluquinconazole; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and prochloraz; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and propiconazole; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and prothioconazole; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and prothioconazole; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and spiroxamine; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and tebuconazole; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and metrafenone;
(A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and bixafen; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and boscalid; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and isopyrazam (9R-component); (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl- 1,2,3 - thiadiazole-5-carboxamide, and isopyrazam (9S-component); (A-13) N-(4-isobutylthiazol-2-yl)- 4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and sedaxane (trans-isomer); (A-13) N-(4- isobutylthiazol-2-yl)-4-cyclopropyl- 1,2,3 -thiadiazole-5-carboxamide, and sedaxane (cis- isomer); (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-13) N-(4-isobutylthiazol-2-yl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and penthiopyrad; (A-13) N-(4-isobutylthiazol-2- yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and azoxystrobin; (A-13) N-(4- isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fluoxastrobin; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and kresoxim- methyl; (A-13) N-(4-isobutyltbiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and picoxystrobin; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and pyraclostrobin; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3- thiadiazole-5-carboxamide, and trifloxystrobin; (A-13) N-(4-isobutylthiazol-2-yl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and quinoxyfen; (A-13) N-(4-isobutylthiazol-2- yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and epoxiconazole; (A-13) N-(4- isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fenpropidin; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and fenpropimorph; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and fluquinconazole; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and prochloraz; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl- 1,2,3 - thiadiazole-5-carboxamide, and propiconazole; (A-13) N-(4-isobutylthiazol-2-yl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and prothioconazole; (A-13) N-(4- isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and prothioconazole; (A-
13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spiroxamine; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and tebuconazole; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and metrafenone;
(A-14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and bixafen; (A-14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and boscalid; (A-14) N- phenylsιUfonyl-4-cydopropyl- 1,2,3 -thiadiazole-5-carboxamide, and isopyrazam (9R- component); (A-14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and isopyrazam (9S-component); (A-14) N-phenylsulfonyl-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and sedaxane (trans-isomer); (A-14) N-phenylsulfonyl-4-cyclopropyl- 1,2,3 - thiadiazole-5-carboxamide, and sedaxane (cis-isomer); (A-14) N-phenylsulfonyl-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-14) N-phenylsulfonyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and penthiopyrad; (A-14) N-phenylsulfonyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and azoxystrobin; (A-
14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and fluoxastrobin; (A- 14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxaniide, and kresoxim-methyl; (A-14) N-phenylsulfonyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and picoxystrobin; (A-14) N-phenylsulfonyl-4-cyclopropyl- 1,2,3 -thiadiazole-5-carboxamide, and pyraclostrobin; (A-14) N-phenylsulfonyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and trifioxystrobin; (A-14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and quinoxyfen; (A- 14) N-phenylsulfonyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and epoxiconazole; (A- 14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and fenpropidin; (A-14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and fenpropimorph; (A-14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and fluquinconazole; (A-14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and prochloraz; (A-14) N- phenylsulfonyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and propiconazole; (A-14) N- phenylsulfonyM-cyclopropyl-l^^-tm'adiazole-S-carboxamide, and prothioconazole; (A-14) N- phenylsulfonyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and prothioconazole; (A-14) N- phenylsulfonyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spiroxamine; (A-14) N- phenylsulfonyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and tebuconazole; (A-14) N- phenylsulfonyl-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and metrafenone;
(A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and bixafen; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and boscalid; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and isopyrazam (9R-component); (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole- 5-carboxamide, and isopyrazam (9S-component); (A-15) N-(3,4-dimethoxybenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxarnide, and sedaxane (trans-isomer); (A-15) N-(3,4- dimethoxybenzy^^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and sedaxane (cis-isomer); (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-15) N-(3,4-dimethoxybenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and penthiopyrad; (A-15) N-(3,4- dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and azoxystrobin; (A-15) N- (3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fluoxastrobin; (A- 15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and kresoxim- methyl; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and picoxystrobin; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l ,2,3-thiadiazole-5- carboxamide, and pyraclostrobin; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5-carboxamide, and trifloxystrobin; (A-15) N-(3,4-dimethoxybenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and quinoxyfen; (A-15) N-(3,4- dimethoxyberizyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and epoxiconazole; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fenpropidin; (A- 15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and fenpropimorph; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and fluquinconazole; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5-carboxamide, and prochloraz; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and propiconazole; (A-15) N-(3,4-dimethoxybenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and prothioconazole; (A-15) N-(3,4- dimethoxybenzyO^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and prothioconazole; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spiroxamine; (A- 15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and tebuconazole; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and metrafenone; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and bixafen; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and boscalid; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and isopyrazam (9R-component); (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl- 1 ,2,3-thiadiazole-5- carboxamide, and isopyrazam (9S-component); (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and sedaxane (trans-isomer); (A-16) N-(3,5-dichlorobenzyl)- 4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and sedaxane (cis-isomer); (A-16) N-(3,5- dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and sedaxane (mixture of cis- /trans-isomers 0-20%: 100-80%); (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and penthiopyrad; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and azoxystrobin; (A-16) N-(3,5-dichlorobenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fluoxastrobin; (A-16) N-(3,5- dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and kresoxim-methyl; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and picoxystrobin; (A- 16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and pyraclostrobin; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and trifloxystrobin; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and quinoxyfen; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and epoxiconazole; (A-16) N-β^-dicMorobenzyl^-cyclopropyl-l^^-thiadiazole-S- carboxamide, and fenpropidin; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole- 5 -carboxamide, and fenpropimorph; (A-16) N-^S-dichlorobenzyl^-cyclopropyl-l^^- thiadiazole-5 -carboxamide, and fluquinconazole; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and prochloraz; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and propiconazole; (A-16) N-(3,5-dichlorobenzyl)-4- cyclopropyl-l^^-thiadiazole-S-carboxamide, and prothioconazole; (A-16) N-(3,5- dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and prothioconazole; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spiroxamine; (A- 16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-tbiadiazole-5-carboxamide, and tebuconazole; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l ,2,3-tbiadiazole-5-carboxamide, and metrafenone;
(A-17) 2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and bixafen; (A-17) 2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and boscalid; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and isopyrazam (9R-component); (A-17) 2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and isopyrazam (9S- component); (A-17) 2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and sedaxane (trans-isomer); (A-17) 2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4- one, and sedaxane (cis-isomer); (A-17) 2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l- benzoxazin-4-one, and sedaxane (mixture of cis-/trans-isomers 0-20%: 100-80%); (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and penthiopyrad; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and azoxystrobin; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and fluoxastrobin; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and kresoxim-methyl; (A-17) 2- (4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and picoxystrobin; (A-17) 2- (4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and pyraclostrobin; (A-17) 2- (4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and trifloxystrobin; (A-17) 2- (4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and quinoxyfen; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and epoxiconazole; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and fenpropidin; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and fenpropimorph; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and fluquinconazole; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and prochloraz; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and propiconazole; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and prothioconazole; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and prothioconazole; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and spiroxamine; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and tebuconazole; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and metrafenone;
(A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and clothianidin; (A-I) octyl 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and imidacloprid; (A-I) octyl 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and fipronil; (A-I) octyl 4-cyclopropyl- l,2,3-thiadiazole-5- carboxylate, and ethiprole; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and β- cyfluthrin; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and tefluthrin; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and methiocarb; (A-I) octyl 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and thiodicarb; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and spinosad; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and rynaxypyr; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and cyazypyr; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiamethoxam; (A-I) octyl 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenamiphos; (A-I) octyl 4-cyclopropyl- 1,2,3- thiadiazole-5 -carboxylate, and aldicarb; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and aldicarb; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and ethoprofos; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and oxamyl; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and deltamethrin; (A-I) octyl 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and spirotetramat; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-
5-carboxylate, and BYI 02960; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and flubendiamide; (A-I) octyl 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiacloprid;
(A-2) (2-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and clothianidin; (A-2) (2-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and imidacloprid; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fipronil; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and ethiprole; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and β-cyfluthrin; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and tefluthrin; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and methiocarb; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiodicarb; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and spinosad; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and rynaxypyr; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and cyazypyr; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiamethoxam; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenamiphos; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and aldicarb; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and aldicarb; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and ethoprofos; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and oxamyl; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and deltamethrin; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and spirotetramat; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and BYI 02960; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and flubendiamide; (A-2) (2- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiacloprid;
(A-3) (3 -chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and clothianidin; (A-3)
(3 -chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and imidacloprid; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fipronil; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and ethiprole; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and β-cyfluthrin; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and tefluthrin; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and methiocarb; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiodicarb; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and spinosad; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and rynaxypyr; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and cyazypyr; (A-3) (3- chloroben2yl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiamethoxam; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenamiphos; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-tbiadiazole-5-carboxylate, and aldicarb; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and aldicarb; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and ethoprofos; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and oxamyl; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and deltamethrin; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and spirotetramat; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and BYI 02960; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and flubendiamide; (A-3) (3- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiacloprid;
(A-4) (4-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and clothianidin; (A-4)
(4-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and imidacloprid; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fipronil; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and ethiprole; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and β-cyfluthrin; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and tefluthrin; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and methiocarb; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiodicarb; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and spinosad; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and rynaxypyr; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and cyazypyr; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiamethoxam; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenamiphos; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and aldicarb; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and aldicarb; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and ethoprofos; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and oxamyl; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and deltamethrin; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and spirotetramat; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and BYI 02960; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and flubendiamide; (A-4) (4- chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiacloprid; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and clothianidin; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and imidacloprid; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and fipronil; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and ethiprole; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl- 1,2,3 -thiadiazole-5 - carboxylate, and β-cyfluthrin; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl- 1, 2,3 -thiadiazole- 5-carboxylate, and tefluthrin; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole- 5-carboxylate, and methiocarb; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3- thiadiazole-5 -carboxylate, and thiodicarb; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and spinosad; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and rynaxypyr; (A-5) (4-chloro-α-methylbenzyl) 4- cyclopropyl-1, 2,3 -thiadiazole-5 -carboxylate, and cyazypyr; (A-5) (4-chloro-α-methylbenzyl) 4- cyclopropyl-1, 2,3 -thiadiazole-5 -carboxylate, and thiamethoxam; (A-5) (4-chloro-α- methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenamiphos; (A-5) (4-chloro- α-methylbenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and aldicarb; (A-5) (4-chloro- α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and aldicarb; (A-5) (4-chloro- α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and ethoprofos; (A-5) (4- chloro-α-methylbenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and oxamyl; (A-5) (4- chloro-α-methylbenzyl) 4-cyclopropyl- 1,2,3 -thiadiazole-5 -carboxylate, and deltamethrin; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and spirotetramat; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and BYI 02960; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl- 1,2,3 -thiadiazole-5 -carboxylate, and flubendiamide; (A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiacloprid;
(A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and clothianidin; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl- 1,2,3 -thiadiazole-5 -carboxylate, and imidacloprid; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and fipronil; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and ethiprole; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole- 5 -carboxylate, and β-cyfluthrin; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3- thiadiazole-5 -carboxylate, and tefluthrin; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and methiocarb; (A-6) (4-methoxycarbonylbenzyl) 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiodicarb; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and spinosad; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and rynaxypyr; (A-6) (4- methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and cyazypyr; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiamethoxam; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and fenamiphos; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and aldicarb; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and aldicarb; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and ethoprofos; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and oxamyl; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5- carboxylate, and deltamethrin; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3- thiadiazole-5-carboxylate, and spirotetramat; (A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate, and BYI 02960; (A-6) (4-methoxycarbonylbenzyl) 4- cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and flubendiamide; (A-6) (4- methoxycarbonylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate, and thiacloprid;
(A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and clothianidin; (A-7) N- benzyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and imidacloprid; (A-7) N-benzyl-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fipronil; (A-7) N-benzyl-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and ethiprole; (A-7) N-benzyl-4-cyclopropyl-l,2,3- thiadiazole-5-carboxamide, and β-cyfluthrin; (A-7) N-benzyl-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and tefluthrin; (A-7) N-benzyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and methiocarb; (A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and thiodicarb; (A-7) N-benzyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spinosad; (A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and rynaxypyr; (A-7) N-benzyl-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and cyazypyr; (A-7) N-benzyl-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and thiamethoxam; (A-7) N-benzyl-4-cyclopropyl-l,2,3- thiadiazole-5-carboxamide, and fenamiphos; (A-7) N-benzyl-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and aldicarb; (A-7) N-benzyM-cyclopropyl-l^S-thiadiazole-S-carboxamide, and aldicarb; (A-7) N-benzyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and ethoprofos; (A-7) N-benzyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and oxamyl; (A-7) N-benzyl-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and deltamethrin; (A-7) N-benzyl-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and spirotetramat; (A-7) N-benzyl-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and BYI 02960; (A-7) N-benzyl-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and flubendiamide; (A-7) N-benzyl-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and thiacloprid;
(A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and clothianidin; (A-
8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and imidacloprid; (A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fipronil; (A-8) N-(4-t- butylbenzyl^-cyclopropyl-l^S-thiadiazole-S-carboxamide, and ethiprole; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and β-cyfluthrin; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and tefluthrin; (A-8) N-(4-t- butylbenzyO^-cyclopropyl-l^.S-thiadiazole-S-carboxamide, and methiocarb; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and thiodicarb; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spinosad; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and rynaxypyr; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and cyazypyr; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and thiamethoxam; (A-8) N-(4-t- butylbenzyO^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and fenamiphos; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and aldicarb; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and aldicarb; (A-8) N-(4-t- butylbenzy^^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and ethoprofos; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and oxamyl; (A-8) N-(4-t- butylbenzy^^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and deltamethrin; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spirotetramat; (A-8) N-(4-t- butylbenzy^^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and BYI 02960; (A-8) N-(4-t- butylbenzy^^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and flubendiamide; (A-8) N-(4-t- butylbenzyl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and thiacloprid;
(A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and clothianidin; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and imidacloprid; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and fϊpronil; (A-9) 3'-chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and ethiprole; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and β-cyfluthrin; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and tefluthrin; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and methiocarb; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and thiodicarb; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and spinosad; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and rynaxypyr; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and cyazypyr; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and thiamethoxam; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and fenamiphos; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and aldicarb; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and aldicarb; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and ethoprofos; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and oxamyl; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and deltamethrin; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and spirotetramat; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and BYI 02960; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and flubendiamide; (A-9) 3'- chloro-4-cyclopropyl-4'-methyl-l,2,3-thiadiazole-5-carboxanilide, and thiacloprid;
(A-IO) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and clothianidin; (A-
10) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-tbiadiazole-5-carboxanilide, and imidacloprid; (A-IO) 4-cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fipronil; (A-10) 4- cyclopropyl-2\4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and ethiprole; (A-10) 4- cyclopropyl^'^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and β-cyfluthrin; (A-10) 4- cydopropyl-2\4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and tefluthrin; (A-10) 4- cyclopropyl^'^'-dimethoxy-l^jS-thiadiazole-S-carboxanilide, and methiocarb; (A-10) 4- cyclopropyl-2\4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and thiodicarb; (A-10) 4- cyclopropyW^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and spinosad; (A-10) 4- cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and rynaxypyr; (A-10) 4- cyclopropyl^'^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and cyazypyr; (A-10) 4- cyclopropyl^'^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and thiamethoxam; (A-10) 4- cyclopropyl^'^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and fenamiphos; (A-10) 4- cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and aldicarb; (A-10) 4- cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and aldicarb; (A-10) 4- cyclopropyl^'^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and ethoprofos; (A-10) 4- cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and oxamyl; (A-10) 4- cyclopropyl-2',4'-dimethoxy-l,2,3-tbiadiazole-5-carboxanilide, and deltamethrin; (A-10) 4- cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and spirotetramat; (A-10) 4- cyclopropyl^'^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and BYI 02960; (A-10) 4- cyclopropyl-2',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and flubendiamide; (A-10) 4- cyclopropyl-2',4'-dimethoxy-l ,2,3-thiadiazole-5-carboxanilide, and thiacloprid;
(A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and clothianidin; (A-
11) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and imidacloprid; (A-I l) 4-cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fϊpronil; (A-I l) 4- cyclopropyl^'^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and ethiprole; (A-I l) 4- cyclopropyl-3',4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and β-cyfluthrin; (A-I l) 4- cyclopropyl-S'^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and tefluthrin; (A-I l) 4- cyclopropyl-S'^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and methiocarb; (A-I l) 4- cyclopropyl-S'^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and thiodicarb; (A-I l) 4- cyclopropyl-3\4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and spinosad; (A-I l) 4- cyclopropyW^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and rynaxypyr; (A-I l) 4- cyclopropyW^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and cyazypyr; (A-I l) 4- cyclopropyl-S'^'-dimethoxy-l^jS-thiadiazole-S-carboxanilide, and thiamethoxam; (A-I l) 4- cyclopropyl-3\4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and fenamiphos; (A-I l) 4- cyclopropyl-S'^'-dimethoxy-l^jS-thiadiazole-S-carboxanilide, and aldicarb; (A-I l) 4- cyclopropyl-3\4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and aldicarb; (A-I l) 4- cyclopropyl-S^'-dimethoxy-l^^-thiadiazole-S-carboxanilide, and ethoprofos; (A-I l) 4- cydopropyl-3\4'-dimethoxy-l,2,3-thiadiazole-5-carboxanilide, and oxamyl; (A-I l) 4- cyclopropyW^'-dimethoxy- 1,2,3 -thiadiazole-5 -carboxanilide, and deltamethrin; (A-I l) 4- cyclopropyl-3\4'-dimethoxy- 1,2,3 -thiadiazole-5 -carboxanilide, and spirotetramat; (A-I l) 4- cyclopropyl-3\4'-dimethoxy- 1,2,3 -thiadiazole-5 -carboxanilide, and BYI 02960; (A-I l) 4- cyclopropyl-S'^'-dimethoxy-l^jS-thiadiazole-S-carboxanilide, and flubendiamide; (A-I l) 4- cyclopropyl-3 ' ,4 ' -dimethoxy- 1 ,2,3 -thiadiazole-5 -carboxanilide, and thiacloprid;
(A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and clothianidin; (A-12) 2'- carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and imidacloprid; (A-12) 2'-carboxy- 4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and fϊpronil; (A-12) 2'-carboxy-4-cyclopropyl- l,2,3-thiadiazole-5-carboxanilide, and ethiprole; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxanilide, and β-cyfluthrin; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxanilide, and tefluthrin; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole- 5 -carboxanilide, and methiocarb; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and thiodicarb; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and spinosad; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and rynaxypyr; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and cyazypyr; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and thiamethoxam; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and fenamiphos; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5- carboxanilide, and aldicarb; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and aldicarb; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and ethoprofos; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and oxamyl; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and deltamethrin; (A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and spirotetramat; (A-12) 2'- carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide, and BYI 02960; (A-12) 2'-carboxy-4- cyclopropyl-l^^-thiadiazole-S-carboxanilide, and flubendiamide; (A-12) 2'-carboxy-4- cyclopropyl-l,2,3-thiadiazole-5 -carboxanilide, and thiacloprid; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and clothianidin; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and imidacloprid; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and fipronil; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and ethiprole; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole- 5-carboxamide, and β-cyfluthrin; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and tefluthrin; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and methiocarb; (A-13) N-(4-isobutylthiazol-2-yl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and thiodicarb; (A-13) N-(4-isobutylthiazol-2- yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spinosad; (A-13) N-(4-isobutylthiazol- 2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and rynaxypyr; (A-13) N-(4- isobutyltruazol^-yl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and cyazypyr; (A-13) N- (4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and thiamethoxam; (A-
13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and fenamiphos; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5 -carboxamide, and aldicarb;
(A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and aldicarb; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and ethoprofos; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and oxamyl; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and deltamethrin; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and spirotetramat; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and BYI 02960; (A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and flubendiamide; (A-13) N-(4-isobutylthiazol-2-yl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and thiacloprid;
(A-14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxarnide, and clothianidin; (A-
14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and imidacloprid; (A-14) N-phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and fipronil; (A-14) N- phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and ethiprole; (A-14) N- phenylsulfonyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and β-cyfluthrin; (A-14) N- phenylsulfonyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and tefluthrin; (A-14) N- phenylsulfonyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and methiocarb; (A-14) N- phenylsulfonyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and thiodicarb; (A-14) N- phenylsulfonyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and spinosad; (A-14) N- phenylsulfonyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and rynaxypyr; (A-14) N- phenylsulfonyl^-cyclopropyl-l^^-thiadiazole-S-carboxamide, and cyazypyr; (A-14) N- phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and thiamethoxam; (A-14) N- phenylsulfonyl^-cyclopropyl-l^S-thiadiazole-S-carboxamide, and fenamiphos; (A-14) N- phenylsulfonyM-cyclopropyl-l^jS-thiadiazole-S-carboxamide, and aldicarb; (A-14) N- phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and aldicarb; (A-14) N- phenylsulfonyM-cyclopropyl-l^jS-thiadiazole-S-carboxamide, and ethoprofos; (A-14) N- phenylsulfonyM-cyclopropyl-l^^-thiadiazole-S-carboxamide, and oxamyl; (A-14) N- phenylsulfonyM-cyclopropyl-l^jS-tln'adiazole-S-carboxamide, and deltamethrin; (A-14) N- phenylsulfonyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spirotetramat; (A-14) N- phenylsulfonyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and BYI 02960; (A-14) N- phenylsulfonyl-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and flubendiamide; (A-14) N- phenylsulfonyM-cyclopropyl-l^jS-thiadiazole-S-carboxamide, and thiacloprid;
(A- 15) N-(3 ,4-dimethoxybenzyl)-4-cyclopropyl- 1 ,2,3-thiadiazole-5 -carboxamide, and clothianidin; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and imidacloprid; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and fipronil; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and ethiprole; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole- 5 -carboxamide, and
Figure imgf000040_0001
(A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and tefluthrin; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and methiocarb; (A-15) N-(3,4-dimethoxybenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and tbiodicarb; (A-15) N-(3,4-dimethoxybenzyl)- 4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and spinosad; (A-15) N-(3,4- dimethoxybenzyl)-4-cyclopropyl-l, 2,3 -thiadiazole-5 -carboxamide, and rynaxypyr; (A-15) N- (3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and cyazypyr; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and thiamethoxam; (A- 15) N-(3 ,4-dimethoxybenzyl)-4-cyclopropyl- 1 ,2,3-thiadiazole-5-carboxamide, and fenamiphos; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and aldicarb; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and aldicarb; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and ethoprofos; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and oxamyl; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and deltamethrin; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and spirotetramat; (A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and BYI 02960; (A-15) N-(3,4-dimethoxybenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and flubendiamide; (A-15) N-(3,4- dimethoxybenzyl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide, and thiacloprid; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and clothianidin; (A- 16) N-(3 ,5 -dichlorobenzy^^-cyclopropyl- 1,2,3 -thiadiazole-5 -carboxamide, and imidacloprid; (A-16) N-(3,5-dichloroben2yl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and fipronil; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and ethiprole; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide, and β-cyfluthrin; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole- 5-carboxamide, and tefluthrin; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole- 5-carboxamide, and methiocarb; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and thiodicarb; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and spinosad; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and rynaxypyr; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and cyazypyr; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3- thiadiazole-5 -carboxamide, and thiamethoxam; (A-16) N-(3,5-dichlorobenzyl)-4-cyclopropyl- l,2,3-thiadiazole-5-carboxamide, and fenamiphos; (A-16) N-(3,5-dichlorobenzyl)-4- cyclopropyl-l^^-thiadiazole-S-carboxamide, and aldicarb; (A-16) N-(3,5-dichlorobenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and aldicarb; (A-16) N-(3,5-dichlorobenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and ethoprofos; (A-16) N-(3,5-dichlorobenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and oxamyl; (A-16) N-(3,5-dichlorobenzyl)-4- cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and deltamethrin; (A-16) N-(3,5-dichlorobenzyl)- 4-cyclopropyl- 1,2,3 -thiadiazole-5 -carboxamide, and spirotetramat; (A-16) N-(3,5- dichlorobenzyl)-4-cyclopropyl- 1,2,3 -thiadiazole-5 -carboxamide, and BYI 02960; (A-16) N- (3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and flubendiamide; (A- 16) N-(3,5-dichlorobenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide, and thiacloprid;
(A-17) 2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and clothianidin; (A- 17) 2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and imidacloprid; (A-17)
2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and fipronil; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and ethiprole; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and β-cyfluthrin; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and tefluthrin; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and methiocarb; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and thiodicarb; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and spinosad; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and rynaxypyr; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and cyazypyr; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and thiamethoxam; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and fenamiphos; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and aldicarb; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and aldicarb; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and ethoprofos; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and oxamyl; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and deltamethrin; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and spirotetramat; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and BYI 02960; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and flubendiamide; (A-17) 2-(4- cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, and thiacloprid;
In conjunction with the present invention compounds (A) and (B) are different from each other.
In the combinations according to the invention the compounds (A) and (B) are present in a synergistically effective weight ratio of A:B in a range of 1000:1 to 1 :1000, preferably in a weight ratio of 500: 1 to 1 :500, most preferably in a weight ratio of 250: 1 to 1 :250. Further ratios of A:B which can be used according to the present invention with increasing preference in the order given are: 1: 100 to 100:1, 95:1 to 1:95, 90:1 to 1 :90, 85:1 to 1 :85, 80:1 to 1 :80, 75: 1 to 1:75, 70:1 to 1:70, 65:1 to 1 :65, 60:1 to 1:60, 55:1 to 1 :55, 50:1 to 1:50, 45:1 to 1 :45, 40:1 to 1:40, 35:1 to 1:35, 30:1 to 1:30, 25:1 to 1 :25, 15:1 to 1:15, 10:1 to 1:10, 5:1 to 1:5, 4:1 to 1:4, 3: 1 to 1:3, 2:1 to 1:2.
Where a compound (A) or a compound (B) can be present in tautomeric form, such a compound is understood hereinabove and hereinbelow also to include, where applicable, corresponding tautomeric forms, even when these are not specifically mentioned in each case.
Compounds (A) or compounds (B) having at least one basic centre are capable of forming, for example, acid addition salts, e.g. with strong inorganic acids, such as mineral acids, e.g. perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted substituted, e.g. halo-substituted, C]-C4 alkanecarboxylic acids, e.g. acetic acid, saturated or unsaturated dicarboxylic acids, e.g. oxalic, malonic, succinic, maleic, fumaric and phthalic acid, hydroxycarboxylic acids, e.g. ascorbic, lactic, malic, tartaric and citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted, e.g. halo-substituted, Ci-C4alkane- or aryl-sulfonic acids, e.g. methane- or p-toluene-sulfonic acid. Compounds (A) or compounds (B) having at least one acid group are capable of forming, for example, salts with bases, e.g. metal salts, such as alkali metal or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri- lower alkylamine, e.g. ethyl-, diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- or tri-hydroxy-lower alkylamine, e.g. mono-, di- or tri-ethanolamine. In addition, corresponding internal salts may optionally be formed. In the context of the invention, preference is given to agrochemically advantageous salts. In view of the close relationship between the compounds (A) or the compounds (B) in free form and in the form of their salts, hereinabove and herein below any reference to the free compounds (A) or free compounds (B) or to their salts should be understood as including also the corresponding salts or the free compounds (A) or free compounds (B), respectively, where appropriate and expedient. The equivalent also applies to tautomers of compounds (A) or compounds (B) and to their salts.
According to the invention the expression "combination" stands for the various combinations of compounds (A) and (B), for example in a single "ready-mix" form, in a combined spray mixture composed from separate formulations of the single active compounds, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. Preferably the order of applying the compounds (A) and (B) is not essential for working the present invention.
The compounds (B) are listed by common names followed by the corresponding CAS-numbers in parenthesis. If no common name was available at the priority date of the application compounds (B) are listed by IUPAC-names followed by the corresponding CAS-numbers in parenthesis.
According to the invention the expression "pathogen" stands for all organisms which cause damages on plants or any part of a plant. Pathogens are for example phytopathogenic fungi, pests, viruses and microorganisms.
According to the invention the expression "fungi" stands for all fungal and chromista organisms.
According to the invention the expression "phytopathogenic fungi" stands for all fungal and chromista organisms which cause damages on plants or any part of a plant. Examples for fungal taxonomic groups are Ascomycota, Basidiomycota, Chytridiomycota, Deuteromycota, Glomeromycota, Microsporidia, Zygomycota, and anamorphic fungi. Examples for Chromista are Oomycota.
According to the invention the expression "microorganisms" stands for all bacterial and protozoan organisms. Examples are Plasmodiophoromycetes. According to the invention the expression "viruses" stands for all viruses which cause damages on plants or any part of a plant. Examples are DNA-, RNA, and DNA and RNA reverse transcribing viruses as well as sub viral agents.
According to the invention the expression "pests" stands for all aschelminthes and panarthropoda organisms which cause damages on plants or any part of a plant. Examples are Nematoda, Arthopoda, Hexapoda and Arachnida.
The active compounds within the composition according to the invention have potent microbicide activity and can be employed for controlling undesired phytopathogenic fungi and/or microorganisms and/or pests, in crop protection or in the protection of materials.
Within the composition according to the invention, pesticide compounds can be employed in crop protection for example for controlling phytopathogenic fungi and/or microorganisms such as Plasmodiophoromycetes, Oomycota, Chytridiomycota, Zygomycota, Ascomycota, Basidiomycota and Deuteromycota.
Within the composition according to the invention, pesticide compounds can be employed in crop protection for controlling microorganisms for example Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Within the composition according to the invention, pesticide compounds can be employed in crop protection for example for controlling pests such as lepidoptera.
The pesticidal combination and/or composition according to the invention can be used to curatively or preventively control the phytopathogenic fungi and/or microorganisms and/or pests of plants or crops. Thus, according to a further aspect of the invention, there is provided a method for curatively or preventively controlling the phytopathogenic fungi and/or microorganisms and/or pests of plants or crops comprising the use of a pesticide composition according to the invention by application to the seed, the plant or to the fruit of the plant or to the soil in which the plant is growing or in which it is desired to grow.
In a further aspect there is provided a composition comprising a combination according to this invention. Preferably the pesticidal composition comprises an agriculturally acceptable support, carrier or filler.
According to the invention, the term "support" denotes a natural or synthetic, organic or inorganic compound with which the active compound of formula (I) is combined or associated to make it easier to apply, notably to the parts of the plant. This support is thus generally inert and should be agriculturally acceptable. The support may be a solid or a liquid. Examples of suitable supports include clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers, water, alcohols, in particular butanol, organic solvents, mineral and plant oils and derivatives thereof. Mixtures of such supports may also be used.
The composition according to the invention may also comprise additional components. In particular, the composition may further comprise a surfactant. The surfactant can be an emulsifier, a dispersing agent or a wetting agent of ionic or non-ionic type or a mixture of such surfactants. Mention may be made, for example, of polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (in particular alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (in particular alkyl taurates), phosphoric esters of polyoxyethylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the present compounds containing sulphate, sulphonate and phosphate functions. The presence of at least one surfactant is generally essential when the active compound and / or the inert support are water-insoluble and when the vector agent for the application is water. Preferably, surfactant content may be comprised from 5% to 40% by weight of the composition.
Colouring agents such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyanblue, and organic pigments such as alizarin, azo and metallophthalocyanine dyes, and trace elements such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts can be used.
Optionally, other additional components may also be included, e.g. protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents. More generally, the active compounds can be combined with any solid or liquid additive, which complies with the usual formulation techniques.
In general, the composition according to the invention may contain from 0.05 to 99% by weight of active compounds, preferably from 10 to 70% by weight.
The combination or composition according to the invention can be used as such, in form of their formulations or as the use forms prepared therefrom, such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifϊable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ULV) liquid, ultra low volume (ULV) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.
The treatment of plants and plant parts with the active compound combination according to the invention is carried out directly or by action on their environment, habitat or storage area by means of the normal treatment methods, for example by watering (drenching), drip irrigation, spraying, atomizing, broadcasting, dusting, foaming, spreading-on, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water- soluble powder for slurry treatment, or by encrusting.
These compositions include not only compositions which are ready to be applied to the plant or seed to be treated by means of a suitable device, such as a spraying or dusting device, but also concentrated commercial compositions which must be diluted before application to the crop.
The active compounds within the composition according to the invention have potent microbicide activity and can be employed for controlling undesired micro-organisms, such as fungi or bacteria, in crop protection or in the protection of materials.
Within the composition according to the invention, pesticide compounds can be employed in crop protection for example for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes as well as all aschelminthes and panarthropoda organisms which cause damages on plants or any part of a plant like Nematoda, Arthopoda, Hexapoda and Arachnida.
Within the composition according to the invention, bactericide compounds can be employed in crop protection for example for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
The pesticide composition according to the invention can be used to curatively or preventively control phytopathogenic fungi and/or pests and/or microorganisms of plants or crops. Thus, according to a further aspect of the invention, there is provided a method for curatively or preventively controlling the phytopathogenic fungi and/or pests and/or microorganisms of plants or crops comprising the use of a pesticide composition according to the invention by application to the seed, the plant or to the fruit of the plant or to the soil in which the plant is growing or in which it is desired to grow. The composition of the invention is also suitable for the treatment of seeds. (A) large part of the damage caused by pests on cultigens occurs by infestation of the seed during storage and after sowing the seed in the ground as well as during and after germination of the plants. This phase is especially critical since the roots and shoots of the growing plant are particularly sensitive and even a small amount of damage can lead to withering of the whole plant.
The method of treatment according to the invention may also be useful to treat propagation material such as tubers or rhizomes, but also seeds, seedlings or seedlings pricking out and plants or plants pricking out. This method of treatment can also be useful to treat roots. The method of treatment according to the invention can also be useful to treat the over-ground parts of the plant such as trunks, stems or stalks, leaves, flowers and fruit of the concerned plant.
Among the plants that can be protected by the method according to the invention, mention may be made of cotton ; flax ; vine ; fruit or vegetable crops such as Rosaceae sp. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana trees and plantins), Rubiaceae sp., Theaceae sp., StercuHceae sp., Rutaceae sp. (for instance lemons, oranges and grapefruit) ; Solanaceae sp. (for instance tomatoes), Liliaceae sp., Asteraceae sp. (for instance lettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp. (for instance strawberries) ; major crops such as Graminae sp. (for instance maize, lawn or cereals such as wheat, rye, rice, barley and triticale), Asteraceae sp. (for instance sunflower), Cruciferae sp. (for instance colza), Fabacae sp. (for instance peanuts), Papilionaceae sp. (for instance soybean), Solanaceae sp. (for instance potatoes), Chenopodiaceae sp. (for instance beetroots) ; horticultural and forest crops ; as well as genetically modified homologues of these crops.
The method of treatment according to the invention can be used in the treatment of genetically modified organisms, e.g. plants or seeds. Genetically modified plants are plants of which a heterologous gene encoding a protein of interest has been stably integrated into genome. The expression "heterologous gene encoding a protein of interest" essentially means genes which give the transformed plant new agronomic properties, or genes for improving the agronomic quality of the modified plant.
A further aspect of the instant invention is a method of protecting natural substances of vegetable or animal origin or their processed forms, which have been taken from the natural life cycle, which comprises applying to said natural substances of vegetable or animal origin or then- processed forms a combination of compounds (A) and (B) in a synergistically effective amount. A preferred embodiment is a method of protecting natural substances of vegetable origin or their processed forms, which have been taken from the natural life cycle, which comprises applying to said natural substances of vegetable origin or their processed forms a combination of compounds (A) and (B) in a synergistically effective amount.
A further preferred embodiment is a method of protecting fruit, preferably pomes, stone fruits, soft fruits and citrus fruits, or their processed forms, which have been taken from the natural life cycle, which comprises applying to said natural substances of vegetable origin or their processed forms a combination of compounds (A) and (B) in a synergistically effective amount.
The combinations of the present invention may also be used in the field of protecting technical material against attack of fungi. According to the instant invention, the term "technical material" includes paper; carpets; constructions; cooling and heating systems; wall-boards; ventilation and air conditioning systems and the like. The combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably "storage goods" is understood to denote wall-boards.
The method of treatment according to the invention can also be used in the field of protecting storage goods against attack of fungi. According to the instant invention, the term "storage goods" is understood to denote natural substances of vegetable or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Storage goods of vegetable origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted. Also falling under the definition of storage goods is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Storage goods of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably "storage goods" is understood to denote natural substances of vegetable origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
In another preferred embodiment of the invention "storage goods" is understood to denote wood. The pesticide combination or composition according to the invention may also be used against fungal diseases liable to grow on or inside timber. The term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting one or more compounds according to the invention, or a composition according to the invention ; this includes for example direct application, spraying, dipping, injection or any other suitable means.
Among the diseases of plants or crops that can be controlled by the method according to the invention, mention may be made of :
Powdery Mildew Diseases such as
Blumeria diseases caused for example by Blumeria graminis
Podosphaera diseases caused for example by Podosphaera leucotricha
Sphaerotheca diseases caused for example by Sphaerotheca fuliginea
Uncinula diseases caused for example by Uncinula necator
Rust Diseases such as
Gymnosporangium diseases caused for example by Gymnosporangium sabinae
Hemileia diseases caused for example by Hemileia vastatrix
Phakopsora diseases caused for example by Phakopsora pachyrhizi and Phakopsora meibomiae
Puccinia diseases caused for example by Puccinia recondite, and Puccinia triticina;
Uromyces diseases caused for example by Uromyces appendiculatus
Oomycete Diseases such as
Bremia diseases caused for example by Bremia lactucae
Peronospora diseases caused for example by Peronospora pisi and Peronospora brassicae
Phytophthora diseases caused for example by Phytophthora infestans
Plasmopara diseases caused for example by Plasmopara viticola
Pseudoperonospora diseases caused for example by Pseudoperonospora humuli and Pseudoperonospora cubensis
Pythium diseases caused for example by Pythium ultimum Leafspot, Leaf blotch and Leaf Blight Diseases such as
Alternaria diseases caused for example by Alternaria solani
Cercospora diseases caused for example by Cercospora beticola
Cladiosporium diseases caused for example by Cladiosporium cucumerinum
Cochliobolus diseases caused for example by Cochliobolus sativus
(Conidiaform: Drechslera, Syn: Helminthosporium);
Colletotrichum diseases caused for example by Colletotrichum lindemuthianum
Cycloconium diseases caused for example by Cycloconium oleaginum
Diaporthe diseases caused for example by Diaporthe citri
Elsinoe diseases caused for example by Elsinoe fawcettii
Gloeosporium diseases caused for example by Gloeosporium laeticolor
Glomerella diseases caused for example by Glomerella cingulata
Guignardia diseases caused for example by Guignardia bidwellii
Leptosphaeria diseases caused for example by Leptosphaeria maculans
Magnaporthe diseases caused for example by Magnaporthe grisea
Mycosphaerella diseases caused for example by Mycosphaerella graminicola and Mycosphaerella fijiensis
Phaeosphaeria diseases caused for example by Phaeosphaeria nodorum
Pyrenophora diseases caused for example by Pyrenophora teres
Ramularia diseases caused for example by Ramularia collo-cygni
Rhynchosporium diseases caused for example by Rhynchosporium secalis
Septoria diseases caused for example by Septoria apii;
Typhula diseases caused for example by Thyphula incarnata Venturia diseases caused for example by Venturia inaequalis
Root- and Stem Diseases such as
Corticium diseases caused for example by Corticium graminearum
Fusarium diseases caused for example by Fusarium oxysporum Gaeumannomyces diseases caused for example by Gaeumannomyces graminis
Rhizoctonia diseases caused for example by Rhizoctonia solani
Oculimacula (Tapesia) diseases caused for example by Oculimacula Tapesia acuformis
Thielaviopsis diseases caused for example by Thielaviopsis basicola
Ear and Panicle Diseases including Maize cob such as Alternaria diseases caused for example by Alternaria spp.
Aspergillus diseases caused for example by Aspergillus flavus
Cladosporium diseases caused for example by Cladiosporium cladosporioides
Claviceps diseases caused for example by Claviceps purpurea
Fusarium diseases caused for example by Fusarium culmorum Gibberella diseases caused for example by Gibberella zeae
Monographella diseases caused for example by Monographella nivalis
Smut- and Bunt Diseases such as
Sphacelotheca diseases caused for example by Sphacelotheca reiliana
Tilletia diseases caused for example by Tilletia caries Urocystis diseases Urocystis occulta
Ustilago diseases caused for example by Ustilago nuda;
Fruit Rot and Mould Diseases such as
Aspergillus diseases caused for example by Aspergillus flavus Botrytis diseases caused for example by Botrytis cinerea
Penicillium diseases caused for example by Penicillium expansum and Penicillium purpurogenum
Sclerotinia diseases caused for example by Sclerotinia sclerotiorum;
Verticillium diseases caused for example by Verticillium alboatrum
Seed- and Soilborne Decay, Mould, Wilt, Rot and Damping-off diseases
Fusarium diseases caused for example by Fusarium culmorum
Phytophthora diseases caused for example by Phytophthora cactorum
Pythium diseases caused for example by Pythium ultimum
Rhizoctonia diseases caused for example by Rhizoctonia solani
Sclerotium diseases caused for example by Sclerotium rolfsii
Canker, Broom and Dieback Diseases such as
Nectria diseases caused for example by Nectria galligena
Blight Diseases such as
Monilinia diseases caused for example by Monilinia laxa
Leaf Blister or Leaf Curl Diseases including deformation of blooms and fruits such as
Taphrina diseases caused for example by Taphrina deformans
Decline Diseases of Wooden Plants such as
Esca disease caused for example by Phaeomoniella clamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea
Diseases of Flowers and Seeds such as
Botrytis diseases caused for example by Botrytis cinerea
Diseases of Tubers such as Rhizoctonia diseases caused for example by Rhizoctonia solani
Helminthosporium diseases caused for example by Helminthosporium solani
Diseases caused by Bacterial Organisms such as
Xanthomanas species for example Xanthomonas campestris pv. Oryzae
Pseudomonas species for example Pseudomonas syringae pv. Lachrymans
Erwinia species for example Erwinia amylovora.
The compounds releated to this invention are preferably used to control the following soybean diseases:
Fungal Diseases of the Foliage, Upper Stems, Pods and Seeds for example
Alternaria leaf spot (Alternaria spec, atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye Leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica Leaf Spot (Phyllosticta sojaecola), Pod and Stem Blight (Phomopsis sojae), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi, Phakopsora meibomiae), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot (Corynespora cassiicola)
Fungal Disease of the Roots and Lower Stems for example
Black Root Rot (Calonectria crotalariae), Charcoal Rot (Macrophomina phaseolina), Fusarium Blight or Wilt, Root Rot, and Pod and Collar Rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Rot (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Stem Blight (Diaporthe phaseolorum), Stem Canker (Diaporthe phaseolorum var. caulivora), Phytophthora Rot (Phytophthora megasperma), Brown Stem Rot (Phialophora gregata), Pythium Rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Rot, Stem Decay, and Damping-Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Rot (Thielaviopsis basicola)
They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include:
From the order of the Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
From the class of the 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., Scoφio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
From the class of the Bivalva, for example, Dreissena spp.
From the order of the Chilopoda, for example, Geophilus spp., Scutigera spp.
From the order of the Coleoptera, for example, Acanthoscelides obtectus, Adoretus spp., Agelastica ami, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., 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.
From the order of the Collembola, for example, Onychiurus armatus. From the order of the Dermaptera, for example, Forfϊcula auricularia.
From the order of the Diplopoda, for example, Blaniulus guttulatus.
From the order of the 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 spp., Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.
From the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
From the class of the 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, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.
It is furthermore possible to control protozoa, such as Eimeria.
From the order of the Heteroptera, for example, Anasa 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.
From the order of the 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, Cameocephala 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, Macrosiphum spp., Mahanarva fϊmbriolata, Melanaphis sacchari, Metcalfϊella 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., Proto- pulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella fiircifera, 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 of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber.
From the order of the Isoptera, for example, Reticulitermes spp., Odontotermes spp.
From the order of the Lepidoptera, for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Caφocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoveφa 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 spp.
From the order of the Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
From the order of the Siphonaptera, for example, Ceratophyllus spp., Xenopsylla cheopis.
From the order of the Symphyla, for example, Scutigerella immaculata.
From the order of the Thysanoptera, for example, Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamom, Thrips spp.
From the order of the Thysanura, for example, Lepisma saccharina.
The 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.
The method of treatment according to the invention also provides the use of compounds (A) and (B) in a simultaneous, separate or sequential manner.
The dose of active compound usually applied in the method of treatment according to the invention is generally and advantageously
for foliar treatments: from 0.1 to 10,000 g/ha, preferably from 10 to 1,000 g/ha, more preferably from 50 to 300g/ha; in case of drench or drip application, the dose can even be reduced, especially while using inert substrates like rockwool or perlite;
- for seed treatment: from 2 to 200 g per 100 kilogram of seed, preferably from 3 to 150 g per 100 kilogram of seed;
for soil treatment: from 0.1 to 10,000 g/ha, preferably from 1 to 5,000 g/ha. The doses herein indicated are given as illustrative examples of the method according to the invention. A person skilled in the art will know how to adapt the application doses, notably according to the nature of the plant or crop to be treated.
The compounds or mixtures according to the invention may also be used for the preparation of composition useful to curatively or preventively treat human or animal fungal diseases such as, for example, mycoses, dermatoses, trichophyton diseases and candidiases or diseases caused by Aspergillus spp., for example Aspergillus fiimigatus.
Mycotoxins
Furthermore compounds or mixtures according to the invention may also be used to reduce the contents of mycotoxins in the harvested crops and therefore in foods and animal feed stuff made therefrom.
Especially but not exclusively the following mycotoxins can be specified:
Deoxynivalenole (DON), Nivalenole, 15-Ac-DON, 3-Ac-DON, T2- und HT2- Toxins, Fumonisines, Zearalenone Moniliformine, Fusarine, Diaceotoxyscirpenole (DAS), Beauvericine, Enniatine, Fusaroproliferine, Fusarenole, Ochratoxines, Patuline, Ergotalcaloides und Aflatoxines, which are caused for example by the following fungal diseases: Fusarium spec., like Fusarium acuminatum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides and others but also by Aspergillus spec, Penicillium spec., Claviceps purpurea, Stachybotrys spec, and others.
Treatment of seeds
The invention comprises a procedure in which the seed is treated at the same time with a compound of Group (A) and a compound selected from group (B). It further comprises a method in which the seed is treated with compound of Group (A) and a compound selected from group (B) separately.
The invention also comprises a seed, which has been treated with a compound of Group (A) and a compound selected from group (B) at the same time. The invention also comprises a seed, which has been treated with a compound of Group (A) and a compound selected from group (B) separately. For the latter seed, the active ingredients can be applied in separate layers. These layers can optionally be separated by an additional layer that may or may not contain an active ingredient.
The mixtures of the invention are particularly suitable for the treatment of seeds. A large part of the damage caused by pests on cultigens occurs by infestation of the seed during storage and after sowing the seed in the ground as well as during and after germination of the plants. This phase is especially critical since the roots and shoots of the growing plant are particularly sensitive and even a small amount of damage can lead to withering of the whole plant. There is therefore considerable interest in protecting the seed and the germinating plant by the use of suitable agents.
The control of pests by treatment of the seeds of plants has been known for a considerable time and is the object of continuous improvement. However, there are a number of problems in the treatment of seed that cannot always be satisfactorily solved. Therefore it is worthwhile to develop methods for the protection of seeds and germinating plants which makes the additional application of plant protection agents after seeding or after germination of the plants superfluous. It is further worthwhile to optimize the amount of the applied active material such that the seed and the germinating plants are protected against infestation by pests as best as possible without the plants themselves being damaged by the active compound applied. In particular, methods for the treatment seed should also take into account the intrinsic insecticidal properties of transgenic plants in order to achieve optimal protection of the seed and germinating plants with a minimal expenditure of plant protection agents.
The present invention relates therefore especially to a method for the protection of seed and germinating plants from infestation with pests in that the seed is treated with the combination/composition of the invention. In addition the invention relates also to the use of the combination/composition of the invention for the treatment seed for protection of the seed and the germinating plants from pests. Furthermore the invention relates to seed which was treated with an combination/ composition of the invention for protection from pests.
One of the advantages of the invention is because of the special systemic properties of the combination/ composition of the invention treatment with these combination/ composition protects not only the seed itself from pests but also the plants emerging after sprouting. In this way the direct treatment of the culture at the time of sowing or shortly thereafter can be omitted.
A further advantage is the synergistic increase in insecticidal activity of the combination/ composition of the invention in comparison to the respective individual active compounds, which extends beyond the sum of the activity of both individually applied active compounds. In this way an optimization of the amount of active compound applied is made possible.
It is also be regarded as advantageous that the mixtures of the invention can also be used in particular with transgenic seeds whereby the plants emerging from this seed are capable of the expression of a protein directed against pests. By treatment of such seed with the agents of the invention certain pests can already be controlled by expression of the, for example, insecticidal protein, and it is additionally surprising that a synergistic activity supplementation occurs with the agents of the invention, which improves still further the effectiveness of the protection from pest infestation.
The agents of the invention are suitable for the protection of seed of plant varieties of all types as already described which are used in agriculture, in greenhouses, in forestry, in garden construction or in vineyards. In particular, this concerns seed of maize, peanut, canola, rape, poppy, olive, coconut, cacao, soy, cotton, beet, (e.g. sugar beet and feed beet), rice, millet, wheat, barley, oats, rye, sunflower, sugar cane or tobacco. The combination/ compositions of the invention are also suitable for the treatment of the seed of fruit plants and vegetables as previously described. Particular importance is attached to the treatment of the seed of maize, soy, cotton, wheat and canola or rape.
As already described, the treatment of transgenic seed with a combination/ composition of the invention is of particular importance. This concerns the seeds of plants which generally contain at least one heterologous gene that controls the expression of a polypeptide with special insecticidal properties. The heterologous gene in transgenic seed can originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seed that contains at least one heterologous gene that originates from Bacillus sp. and whose gene product exhibits activity against the European corn borer and/or western corn rootworm. Particularly preferred is a heterologous gene that originates from Bacillus thuringiensis.
Within the context of the present invention the combination/ composition of the invention is applied to the seed alone or in a suitable formulation. Preferably the seed is handled in a state in which it is so stable, that no damage occurs during treatment. In general treatment of the seed can be carried out at any time between harvest and sowing. Normally seed is used that was separated from the plant and has been freed of spadix, husks, stalks, pods, wool or fruit flesh. Use of seed that was harvested, purified, and dried to moisture content of below 15 % w/w. Alternatively, seed treated with water after drying and then dried again can also be used. In general care must be taken during the treatment of the seed that the amount of the combination/ composition of the invention and/or further additive applied to the seed is so chosen that the germination of the seed is not impaired and the emerging plant is not damaged. This is to be noted above all with active compounds which can show phytotoxic effects when applied in certain amounts.
The combination/ compositions of the invention can be applied directly, that is without containing additional components and without being diluted. It is normally preferred to apply the combination/ composition to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to the person skilled in the art and are described, for example, in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 Al, WO 2002/080675 Al, WO 2002/028186 A2.
According to another aspect of the present invention, in the combination or composition according to the invention, the compound ratio A/B may be advantageously chosen so as to produce a synergistic effect. The term synergistic effect is understood to mean in particular that defined by Colby in an article entitled "Calculation of the synergistic and antagonistic responses of herbicide combinations" Weeds, (1967), 15, pages 20-22.
The latter article mentions the formula:
XY
E=X+Y —
100
wherein E represents the expected percentage of inhibition of the pest for the combination of the two compounds at defined doses (for example equal to x and y respectively), X is the percentage of inhibition observed for the pest by compound (A) at a defined dose (equal to x), Y is the percentage of inhibition observed for the pest by compound (B) at a defined dose (equal to y). When the percentage of inhibition observed for the combination is greater than E, there is a synergistic effect.
The term "synergistic effect" also means the effect defined by application of the Tammes method, "Isoboles, a graphic representation of synergism in pesticides", Netherlands Journal of Plant Pathology, 70(1964), pages 73-80.

Claims

Claims:
1. A combination comprising
(A) At least one 1,2,3-thiadiazole compound represented by formula (I)
Figure imgf000062_0001
(I)
wherein R1 represents:
(a)
-C(=W')YR2
wherein R2 represents a hydrogen atom; (C]-C2o)alkyl; halo(Ci-C2o)alkyl; (C2-C2o)alkenyl; halo(C2-C20)alkenyl; (C2-C20)alkynyl; halo(C2-C2o)alkynyl; (C3-Ci2)cycloalkyl; halo(C3- C12)cycloalkyl; (C,-C6)alkoxy(CrC6)alkyl; (CrC6)alkylthio(CrC6)alkyl; aryl(C,-C6)alkyl which may be substituted on its ring with a substituent Z; aryloxy (CrC6)alkyl which may be substituted on its ring with a substituent Z; arylthio(Ci-C6)alkyl which may be substituted on its ring with a substituent Z; aryl which may be substituted with a substituent Z; carboxy(Ci-C6)alkyl; (Ci-C6)alkoxycarbonyl(Ci-C6)alkyl; carbamoyl(CrC6)alkyl; carbamoyl^! -C6)alkyl, having on the nitrogen atom 1 or 2 substituents which are the same or different and are selected from (Ci-Cio)alkyl, halo(C]-Cio)alkyl, (C2-C]0)alkenyl, (C3-Cio)cycloalkyl, phenyl which may be substituted with a substituent Z, or phenyl(Ci- C6) alkyl which may be substituted on its ring with a substituent Z; cyano(Ci-C6)alkyl; a heterocyclic ring which may be substituted with a substituent Z; heterocyclic (Ci-C6)alkyl which may be substituted on its ring with a substituent Z; (Ci-C2o)alkylcarbonyl; (C2-
C2o)alkynylcarbonyl; (C2-C6)alkenylcarbonyl; (C3-C6)cycloalkylcarbonyl; phenylcarbonyl which may be substituted with a substituent Z; heterocyclic carbonyl which may be substituted with a substituent Z; (Ci-C2o)alkylsulfonyl; halo(Ci-C2o)alkylsulfonyl; arylsulfonyl which may be substituted with a substituent Z; aryl(Ci-C6)alkylsulfonyl which may be substituted on its ring with a substituent Z; -C(=W2)NR3R4
wherein R3 and R4 are the same or different and each represents a hydrogen atom, (Q - Cio)alkyl, halo(Ci-Cio) alkyl, (C2-Ci0)alkenyl, (C3-Ci0)cycloalkyl, phenyl which may be substituted with a substituent Z, phenyl(Ci-C6)alkyl which may be substituted on its ring with a substituent Z, (Ci-C6)alkoxy, phenoxy which may be substituted with a substituent Z or phenyl(Ci-C6)alkyloxy which may be substituted on its ring with a substituent Z, or R3 and R4 may be taken together to form (C2-C6)alkylene which may be interrupted by an oxygen atom, a sulfur atom or NR5 wherein R5 represents a hydrogen atom, (Ci-C6)alkyl or phenyl which may be substituted with a substituent Z, and W2 represents an oxygen atom or a sulfur atom; -Sθ2NR3R4 wherein R3 and R4 have the same meanings as defined above; or -N=C(R3)R4 wherein R3 and R4 have the same meanings as defined above, Y represents an oxygen atom; a sulfur atom; -N(R6)- wherein R6 represents a hydrogen atom, (Ci-C6)alkyl, (C3-C6)cycloalkyl, phenyl which may be substituted with a substituent Z, phenyl(Ci-C6)alkyl which may be substituted with a substituent Z, (Q- Cio)alkylcarbonyl, (C2-C i0)alkynylcarbonyl, (C2-Cio)alkenylcarbonyl, (C3-
C6)cycloalkylcarbonyl, phenylcarbonyl which may be substituted with a substituent Z, or heterocyclic ring-carbonyl which may be substituted with a substituent Z; or -N(R6)O- wherein R6 has the same meaning as defined above,
and W1 represents an oxygen atom or a sulfur atom,
(b)
a group represented by the following formula
Figure imgf000063_0001
wherein n represents an integer of from 0 to 4, and W3 and W4 are the same or different and each represents an oxygen atom or a sulfur atom,
or
(c) cyano,
and
(B) at least one further active compound selected from the group consisting of (B-I) Inhibitors of the nucleic acid synthesis, for example benalaxyl, benalaxyl-M, bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M, ofurace, oxadixyl and oxolinic acid.
(B-2) Inhibitors of the mitosis and cell division, for example benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fuberidazole, pencycuron, thiabendazole, thiophanate, thiophanate-methyl and zoxamide.
(B-3) Inhibitors of the respiration, for example difiumetorim as CI-respiration inhibitor; bixafen, boscalid, carboxin, fenfuram, flutolanil, fluopyram, furametpyr, furmecyclox, isopyrazam (9R-component), isopyrazam (9S-component), mepronil, oxycarboxin, penthiopyrad, thifluzamide as CII-respiration inhibitor; amisulbrom, azoxystrobin, cyazofamid, dimoxystrobin, enestroburin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyribencarb, trifloxystrobin as CHI-respiration inhibitor.
(B-4) Compounds capable to act as an uncoupler, like for example binapacryl, dinocap, fluazinam and meptyldinocap.
(B-5) Inhibitors of the ATP production, for example fentin acetate, fentin chloride, fentin hydroxide, and silthiofam.
(B-6) Inhibitors of the amino acid and/or protein biosynthesis, for example andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim and pyrimethanil.
(B-7) Inhibitors of the signal transduction, for example fenpiclonil, fludioxonil and quinoxyfen.
(B-8) Inhibitors of the lipid and membrane synthesis, for example biphenyl, chlozolinate, edifenphos, etridiazole, iodocarb, iprobenfos, iprodione, isoprothiolane, procymidone, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-methyl and vinclozolin. (B-9) Inhibitors of the ergosterol biosynthesis, for example aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemoφh, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimoφh, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol, pefurazoate, penconazole, piperalin, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon, triadimenol, tridemoφh, triflumizole, triforine, triticonazole, uniconazole, viniconazole and voriconazole.
(B-IO) Inhibitors of the cell wall synthesis, for example benthiavalicarb, dimethomoφh, fiumoφh, iprovalicarb, mandipropamid, polyoxins, polyoxorim, prothiocarb, validamycin A, and valiphenal.
(B-I l) Inhibitors of the melanine biosynthesis, for example caφropamid, diclocymet, fenoxanil, phthalide, pyroquilon and tricyclazole.
(B- 12) Compounds capable to induce a host defence, like for example acibenzolar-S-methyl, probenazole, and tiadinil.
(B- 13) Compounds capable to have a multisite action, like for example bordeaux mixture, captafol, captan, chlorothalonil, copper naphthenate, copper oxide, copper oxychloride, copper preparations such as copper hydroxide, copper sulphate, dichlofluanid, dithianon, dodine, dodine free base, ferbam, fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper, propamidine, propineb, sulphur and sulphur preparations including calcium polysulphide, thiram, tolylfluanid, zineb and ziram.
(B-14) Further compounds like for example 2,3-dibutyl-6-chlorothieno[2,3- d]pyrimidin-4(3H)-one, ethyl (2Z)-3-amino-2-cyano-3-phenylprop-2- enoate, N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl-lH- pyrazole-4-carboxamide, N- {2-[ 1 , 1 '-bi(cyclopropyl)-2-yl]phenyl} -3- (difluoromethyl)- 1 -methyl- 1 H-pyrazole-4-carboxamide, 3-
(difluoromethyl)- 1 -methyl-N-(3 ',4',5 '-trifluorobiphenyl-2-yl)- 1 H- pyrazole-4-carboxamide, 3-(difluoromethyl)-N-[4-fluoro-2-
(1,1,2,3,3 ,3-hexafluoropropoxy)phenyl] - 1 -methyl- 1 H-pyrazole-4-
5 carboxamide, (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5- fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N- methylethanamide, (2E)-2- {2-[( {[(2E,3E)-4-(2,6-dichlorophenyl)but-3- en-2-ylidene]amino} oxy)methyl]phenyl} -2-(methoxyimino)-N- methylethanamide, 2-chloro-N-( 1,1,3 -trimethyl-2,3 -dihydro- 1 H-inden-
10 4-yl)pyridine-3 -carboxamide, N-(3 -ethyl-3 ,5 ,5 -trimethylcyclohexyl)-3 -
(formylamino)-2-hydroxybenzamide, 5-methoxy-2-methyl-4-(2-
{ [( {( 1 E)- 1 -[3-(trifluoromethyl)phenyl]ethylidene} amino)oxy] methyl}phenyl)-2,4-dihydro-3H-l,2,4-triazol-3-one, (2E)-2-
(methoxyimino)-N-methyl-2-(2- { [( {( 1 E)- 1 -[3-
15 (trifluoromethyl)phenyl]ethylidene}amino)oxy] methyl }phenyl)ethanamide, (2E)-2-(methoxyimino)-N-methyl-2- {2- [(E)-( { 1 -[3-(trifluoromethyl)phenyl]ethoxy} imino) methyl]phenyl}ethanamide, (2E)-2-{2-[({[(lE)-l-(3-{[(E)-l-fluoro-2- phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-
20 (methoxyimino)-N-methylethanamide, l-(4-chlorophenyl)-2-(lH-l,2,4- triazol-1 -yl)cycloheptanol, methyl 1 -(2,2-dimethyl-2,3-dihydro-lH- inden- 1 -yl)- 1 H-imidazole-5-carboxylate, N-ethyl-N-methyl-N'- {2- methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl} imidoformamide, N'- {5-(difluoromethyl)-2-methyl-4-[3-
25 (trimethylsilyl)propoxy]phenyl} -N-ethyl-N-methylimidoformamide, O-
{l-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl} lH-imidazole-1- carbothioate, N-[2-(4- { [3-(4-chlorophenyl)prop-2-yn- 1 -yl]oxy } -3- methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamide, 5-chloro-7-(4- methylpiperidin- 1 -yl)-6-(2,4,6-trifluorophenyl)[ 1 ,2,4]triazolo[ 1,5-
30 a]pyrimidine, 5-amino-l,3,4-thiadiazole-2 -thiol, propamocarb-fosetyl,
1 -[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl 1 H-imidazole- 1 - carboxylate, 1 -methyl-N-[2-(l , 1 ,2,2-tetrafluoroethoxy)phenyl]-3-
(trifluoromethyl)- 1 H-pyrazole-4-carboxamide, 2,3 ,5,6-tetrachloro-4- (methylsulfonyl)pyridine, 2-butoxy-6-iodo-3-propyl-4H-chromen-4-
35 one, 2-phenylphenol and salts, 3-(difluoromethyl)-l-methyl-N-[2-
(1,1 ,2,2-tetrafluoroethoxy)phenyl]- 1 H-pyrazole-4-carboxamide, 3 ,4,5- trichloropyridine-2,6-dicarbonitrile, 3-[5-(4-chlorophenyl)-2,3- dimethylisoxazolidin-3-yl]pyridine, 3-chloro-5-(4-chlorophenyl)-4- (2,6-difluorophenyl)-6-methylpyridazine, 4-(4-chlorophenyl)-5-(2,6- difluorophenyl)-3,6-dimethylpyridazine, quinolin-8-ol, quinolin-8-ol sulfate (2:1) (salt), 5-methyl-6-octyl-3,7-dihydro[l,2,4]triazolo[l,5- a]pyrimidin-7 -amine, 5-ethyl-6-octyl-3,7-dihydro[l,2,4]triazolo[l,5- a]pyrimidin-7-amine, benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, chloroneb, cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, dazomet, debacarb, dichlorophen, diclomezine, dicloran, difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomate, ferimzone, flumetover, fluopicolide, fluoroimide, flusulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl- sodium, hexachlorobenzene, irumamycin, isotianil, methasulfocarb, methyl (2E)-2- {2-[( {cyclopropyl[(4-methoxyphenyl)imino]methyl} thio)methyl]phenyl}-3-methoxyacrylate, methyl isothiocyanate, metrafenone, (5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4- trimethoxy-6-methylphenyl)methanone, mildiomycin, tolnifanide, N- (4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-l-yloxy)phenyl] propanamide, N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4- (prop-2-yn-l-yloxy)phenyl]propanamide, N-[(5-bromo-3- chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide, N-[ 1 - (5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3- carboxamide, N-[ 1 -(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4- iodopyridine-3-carboxamide, N-{(Z)-[(cyclopropylmethoxy)imino][6- (difluoromethoxy)-2,3-difluorophenyl]methyl} -2-phenylacetamide, N-
{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3- difluorophenyl]methyl} -2-phenylacetamide, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts, phenazine-1-carboxylic acid, phenothrin, phosphorous acid and its salts, propamocarb fosetylate, propanosine-sodium, proquinazid, pyrrolnitrine, quintozene, S-prop-2- en-l-yl 5-amino-2-(l-methylethyl)-4-(2-methylphenyl)-3-oxo-2,3- dihydro-lH-pyrazole-1-carbothioate, tecloftalam, tecnazene, triazoxide, trichlamide, 5-chloro-N'-phenyl-N'-prop-2-yn-l -ylthiophene-2- sulfonohydrazide and zarilatnid,
(B-15) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g. alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, and xylylcarb; or
organophosphates, e.g. acephate, azamethiphos, azinphos (-methyl, - ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chloφyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S- methylsulphon, dialifos, diazinon, dichlofenthion, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl, O-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (- methyl/-ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/ -ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion, and imicyafos.
(B- 16) GABA-gated chloride channel antagonists, for example
organochlorines, e.g. camphechlor, chlordane, endosulfan, gamma- HCH, HCH, heptachlor, lindane, and methoxychlor; or
fϊproles (phenylpyrazoles), e.g. acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, and vaniliprole.
(B- 17) Sodium channel modulators/voltage-dependent sodium channel blockers, for example pyrethroids, e.g. acrinathrin, allethrin (d-cis-trans, d-trans), beta- cyfluthrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis- cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, deltamethrin, empenthrin (IR isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda- cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin (IR trans isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (-1R- isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum), eflusilanat;
DDT; or methoxychlor.
(B- 18) Nicotinergic acetylcholine receptor agonists/antagonists, for example
chloronicotinyls, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, imidaclothiz, nitenpyram, nithiazine, thiacloprid, thiamethoxam, AKD- 1022,
nicotine, bensultap, cartap, thiosultap-sodium, and thiocylam.
(B- 19) Allosteric acetylcholine receptor modulators (agonists), for example
spinosyns, e.g. spinosad and spinetoram.
(6) Chloride channel activators, for example
mectins/macrolides, e.g. abamectin, emamectin, emamectin benzoate, ivermectin, lepimectin, and milbemectin; or
juvenile hormone analogues, e.g. hydroprene, kinoprene, methoprene, epofenonane, triprene, fenoxycarb, pyriproxifen, and diofenolan.
(B-20) Active ingredients with unknown or non-specific mechanisms of action, for example gassing agents, e.g. methyl bromide, chloropicrin and sulfiiryl fluoride;
selective antifeedants, e.g. cryolite, pymetrozine, pyrifluquinazon and flonicamid; or
mite growth inhibitors, e.g. clofentezine, hexythiazox, etoxazole.
(B-21) Oxidative phosphorylation inhibitors, ATP disruptors, for example
diafenthiuron;
organotin compounds, e.g. azocyclotin, cyhexatin and fenbutatin oxide; or
propargite, tetradifon.
(B-22) Oxidative phoshorylation decouplers acting by interrupting the H proton gradient, for example chlorfenapyr, binapacryl, dinobuton, dinocap and DNOC.
(B-23) Microbial disruptors of the insect gut membrane, for example Bacillus thuringiensis strains.
(B-24) Chitin biosynthesis inhibitors, for example benzoylureas, e.g. bistrifluron, chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron or triflumuron.
(B-25) Buprofezin.
(B-26) Moulting disruptors, for example cyromazine.
(B-27) Ecdysone agonists/disruptors, for example
diacylhydrazines, e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide, and Fufenozide (JSl 18); or
azadirachtin.
(B-27) Octopaminergic agonists, for example amitraz. (B-28) Site III electron transport inhibitors/site II electron transport inhibitors, for example hydramethylnon; acequinocyl; fluacrypyrim; or cyflumetofen and cyenopyrafen.
(B-29) Electron transport inhibitors, for example
Site I electron transport inhibitors, from the group of the METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, and rotenone; or
voltage-dependent sodium channel blockers, e.g. indoxacarb and metaflumizone.
(B-30) Fatty acid biosynthesis inhibitors, for example tetronic acid derivatives, e.g. spirodiclofen and spiromesifen; or
tetramic acid derivatives, e.g. spirotetramat.
(B-31) Neuronal inhibitors with unknown mechanism of action, e.g. bifenazate.
(B-32) Ryanodine receptor effectors, for example diamides, e.g. fiubendiamide, (R)1(S)-S-ChIOrO-N1 - {2-methyl-4-[ 1 ,2,2,2-tetrafluoro- 1 - (trifluoromethyl)ethyl]phenyl} -N2-( 1 -methyl-2-methylsulphonyl- ethyl)phthalamide, chlorantraniliprole (Rynaxypyr), or Cyantraniliprole (Cyazypyr).
(B-33) Further active ingredients with unknown mechanism of action, for example amidoflumet, fenamiphos, aldicarb, ethoprofos, oxamyl, benclothiaz, benzoximate, bromopropylate, buprofezin, chinomethionat, chlordimeform, chlorobenzilate, clothiazoben, cycloprene, dicofol, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure, japonilure, metoxadiazone, petroleum, potassium oleate, pyridalyl, sulfluramid, tetrasul, triarathene or verbutine; or one of the following known active compounds
4-{[(6-brompyrid-3-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (known from WO
2007/115644), 4-{[(6-fluoφyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on (known from WO 2007/115644), 4-{[(2-chlor-l,3-thiazol-5-yl)methyl](2- fluorethyl)amino}furan-2(5H)-on (known from WO 2007/115644), 4-{[(6-chlorpyrid-3- yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (known from WO 2007/ 115644), 4- {[(6-chloφyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on known from WO 2007/115644), 4-{[(6-chlor-5-fluoφyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (known from WO 2007/115643), 4-{[(5,6-dichlθφyrid-3-yl)methyl](2- fluorethyl)amino}furan-2(5H)-on (known from WO 2007/115646), 4-{[(6-chlor-5- fluoφyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (known from WO 2007/115643), 4-{[(6-chloφyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on
(known from EP-A-O 539 588), 4-{[(6-chloφyrid-3-yl)methyl](methyl)amino}furan- 2(5H)-on (known from EP-A-O 539 588), [(6-chloφyridin-3-yl)methyl](methyl)oxido- λ4-sulfanylidencyanamid (known from WO 2007/149134), [l-(6-chlθφyridin-3- yl)ethyl](methyl)oxido-λ4-sulfanylidencyanamid (known from WO 2007/149134) and its diastereomeres (A) and (B)
Figure imgf000072_0001
(A) (B)
(also known from WO 2007/149134), [(6-trifluormethylpyridin-3- yl)methyl](methyl)oxido-λ4-sulfanylidencyanamid (known from WO 2007/095229), or [ 1 -(6-trifluormethylpyridin-3-yl)ethyl](methyl)oxido-λ4-sulfanylidencyanamid (known from WO 2007/149134) and its diastereomeres (C) and (D), namely Sulfoxaflor
Figure imgf000072_0002
(C) (D).
(also known from WO 2007/149134).
2. Combination according to claim 1 wherein the 1,2,3-thiadiazole compound according to formula (I) is selected from the group consisting of
(A- 1 ) octyl 4-cyclopropyl- 1 ,2,3 -thiadiazole-5 -carboxylate,
(A-2) (2-chlorobenzyl) 4-cyclopropyl- 1 ,2,3-thiadiazole-5-carboxylate,
(A-3) (3-chlorobenzyl) 4-cyclopropyl- l,2,3-thiadiazole-5-carboxylate,
(A-4) (4-chlorobenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate,
(A-5) (4-chloro-α-methylbenzyl) 4-cyclopropyl-l,2,3-thiadiazole-5-carboxylate,
(A-6) (4-methoxycarbonylbenzyl) 4-cyclopropyl- 1 ,2,3-thiadiazole-5-carboxylate,
(A-7) N-benzyl-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide,
(A-8) N-(4-t-butylbenzyl)-4-cyclopropyl-l ,2,3-thiadiazole-5-carboxamide,
(A-9) 3 ' -chloro^-cyclopropyM ' -methyl- 1,2,3 -thiadiazole-5 -carboxanilide,
(A- 10) 4-cyclopropyl-2 ' ,4 ' -dimethoxy- 1 ,2,3 -thiadiazole-5 -carboxanilide,
(A-11) 4-cyclopropyl-3 ',4' -dimethoxy- 1 ,2,3-thiadiazole-5-carboxanilide,
(A-12) 2'-carboxy-4-cyclopropyl-l,2,3-thiadiazole-5-carboxanilide,
(A-13) N-(4-isobutylthiazol-2-yl)-4-cyclopropyl-l,2,3-thiadiazole-5-carboxamide,
(A- 14) N-phenylsulfonyl-4-cyclopropyl- 1 ,2,3 -thiadiazole-5 -carboxamide,
(A-15) N-(3,4-dimethoxybenzyl)-4-cyclopropyl-l,2,3-thiadiazole-5- carboxamide,
(A-16) N-βjS-dichlorobenzyl^-cyclopropyl-l^^-thiadiazole-S- carboxamide,
(A-17) 2-(4-cyclopropyl-l,2,3-thiadiazol-5-yl)-4H-3,l-benzoxazin-4-one, or a salt thereof.
3. Combination according to claims 1 or 2 wherein mixing partners (B) selected from the group consisting of bixafen, boscalid, isopyrazam (9R-component), isopyrazam (9S- component), sedaxane (trans-isomer), sedaxane (cis-isomer), sedaxane (mixture of cis-
/trans-isomers 0-20%: 100-80%), penthiopyrad, azoxystrobin, fluoxastrobin, kresoxim- methyl, picoxystrobin, pyraclostrobin, trifloxystrobin, quinoxyfen, epoxiconazole, fenpropidin, fenpropimoφh, fluquinconazole, prochloraz, propiconazole, prothioconazole, spiroxamine, tebuconazole, metrafenone, clothianidin, imidacloprid, fϊpronil, ethiprole, β-cyfluthrin, tefluthrin, methiocarb, thiodicarb, spinosad, rynaxypyr, cyazypyr, thiamethoxam, fenamiphos, aldicarb, ethoprofos, oxamyl, deltamethrin, spirotetramat, BYI 02960, flubendiamide, thiacloprid.
4. Combination according to claims 1 to 3 comprising mixing partners (A):(B) in a weight ratio of 1 :1000 to 1000:1.
5. Combination according to claims 1 to 4 being a pesticidally active combination.
6. A composition comprising a combination according to claims 1 to 5.
7. A composition according to claim 6 further comprising adjuvants, solvents, carrier, surfactants or extenders.
8. A method for curatively or preventively controlling the phytopathogenic fungi and/or pests and/or microorganisms of plants or crops comprising the use of a pesticide composition according to claims 6 to 7 by application to the seed, the plant or to the fruit of the plant or to the soil in which the plant is growing or in which it is desired to grow.
9. The method according to claim 8 comprising applying the mixing partners (A) and (B) simultaneously or sequentially.
10. The method according to claims 8 or 9 wherein the amount of the combination of claims 1 to 6 is from 0.1 g/ha to 10 kg/ha for foliar and soil treatment and from 2 to 200 g/ 100 kg of seed for seed treatment.
11. Use of a combination according to any of claims 1 to 5 for the treatment of seed.
12. Use according to claim 11 for the treatment of transgenic seed.
13. Method for protecting a seed and/or shoots and foliage of a plant grown from the seed from damage by phytopathogenic fungi and/or pests and/or microorganisms, the method comprising treating an unsown seed with a combination according to any of claims 1 to 5/
14. Method according to claim 13, wherein the seed is treated with component (A) at the same time that it is treated with component(s) (B).
15. Method according to claim 13, wherein the seed is treated with component (A) at a different time than it is treated with component(s) (B).
16. Seed that has been treated with a combination according to any of claims 1 to 5.
PCT/EP2009/006202 2008-09-03 2009-08-27 Synergistic combinations of thiadiazol carbonic acid derivatives WO2010025870A1 (en)

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