WO2011056463A4 - Fungicidal mixtures - Google Patents

Fungicidal mixtures Download PDF

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Publication number
WO2011056463A4
WO2011056463A4 PCT/US2010/053679 US2010053679W WO2011056463A4 WO 2011056463 A4 WO2011056463 A4 WO 2011056463A4 US 2010053679 W US2010053679 W US 2010053679W WO 2011056463 A4 WO2011056463 A4 WO 2011056463A4
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Prior art keywords
fungicides
methyl
chloro
phenyl
composition
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PCT/US2010/053679
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French (fr)
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WO2011056463A3 (en
WO2011056463A2 (en
Inventor
Vann Gregory
Andrew Edmund Taggi
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E. I. Du Pont De Nemours And Company
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Publication of WO2011056463A3 publication Critical patent/WO2011056463A3/en
Publication of WO2011056463A4 publication Critical patent/WO2011056463A4/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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3

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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)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Disclosed is a fungicidal composition comprising (a) at least one compound selected from the compounds of Formula 1, N-oxides, and salts thereof, wherein R1, R2, Q1 and Q2 are as defined in the disclosure; and (b) at least one additional fungicidal compound. Also disclosed is a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of a compound of Formula 1, an N-oxide, or salt thereof (e.g., as a component in the aforesaid composition). Also disclosed is a composition comprising: (a) at least one compound selected from the compounds of Formula 1 described above, N-oxides, and salts thereof; and at least one invertebrate pest control compound or agent.

Claims

AMENDED CLAIMS
received by the International Bureau on 30 September 2011 (30.09.2011 ).
What is claimed is:
1. A fungicidal composition comprising:
(a) at least one compound selected from the compounds of Formula 1, N-oxides, and salts thereof:
Figure imgf000002_0001
wherein
Q1 is phenyl, thienyl, thiazolyl, pyrazolyl, irnidazolyl, pyridinyl, pyridazinyl,
pyrimidinyl, quinolinyl or benzyl, each optionally substituted with up to 4 substituents independently selected from R3 on carbon atom ring members and R4 on nitrogen atom ring members;
Q2 is phenyl, thienyl, thiazolyl, pyrazolyl, irnidazolyl, pyridinyl, pyridazinyl,
pyrimidinyl, quinolinyl or benzyl, each optionally substituted with up to 4 substituents independently selected from R5 on carbon atom ring members and R6 on nitrogen atom ring members;
R1 and R2 are independently halogen, cyano, nitro, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, cyclopropyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 haloalkylthio or C1-C7 hydroxyalkyl;
each R3 and R5 is independently halogen, cyano, hydroxy, nitro, C1-C7 alkyl, C2- C7 alkenyl, C2-C7 alkynyl, C2-C7 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C10
allcylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C3-C7 cycloalkoxy, C3-C7 halocycloalkoxy, C1-C7 alkoxy, C2-C7 cyanoalkoxy, C1-C7 haloalkoxy, C1-C6 alkylthio, C1-C7 haloalkylthio, C1-C7 alkylsulfinyl, C1-C7 alkylsulfonyl, C1-C7 haloalkylsulfinyl, C1-C7 haloalkylsulfonyl, C1- C7 alkylamino, C2-C7 dialkylamino, C2-C7 allcylcarbonyl, C2-C7
alkoxycarbonyl, aminocarbonyl, C2-C7 alkylaminocarbonyl, C3-C7 dialkylaminocarbonyl, C2-C7 alkylcarbonylamino, C3-C]0 trialkylsilyl, - SCN, C(=S)NH2 or -X-U-Z;
each R4 and R6 is independently cyano, CrC6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C C6 haloalkyl, C3-C6 cycloalkyl, CrC6 alkoxy, C2-C6 alkoxyalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminoalkyl or C3-Cg dialkylaminoalkyl ;
each X is independently O, S(— 0)n, NR7 or a direct bond;
each U is independently C]-C6 alkylene, C2-C6 alkenylene, C3-C6 alkynylene,
C3-C6 cycloalkylene or C3-C6 cycloalkenylene, wherein up to 3 carbon atoms are independently selected from C(=0), each optionally substituted with up to 5 substituents independently selected from halogen, cyano, nitro, hydroxy, C}-C6 alkyl, C C6 haloalkyl, Ci-Cg alkoxy and C1-C6 haloalkoxy;
each Z is independently NR8aR8b, ORJ or S(=0)nRl°;
each R7 is independently H, C1-C6 alkyl, i~C6 haloalkyl, C2-C6 allcylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6
alkoxy(thiocarbonyl), C4-Cg cycloalkylcarbonyl, C4-Cg cycloalkoxycarbonyl, C4-Cg (cycloalkylthio)carbonyl or C4-Cg cycloalkoxy(thiocarbonyl);
each R8a and R8b is independently H, C C6 alkyl, CrC6 haloalkyl, C2-C6 alkenyl, C3-C5 alkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6
alkylcarbonyl, C2-C5 alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6 alkoxy(thiocarbonyl), C4-Cg cycloalkylcarbonyl, C4-Cg cycloalkoxycarbonyl, C4-Cg (cycloalkylthio)carbonyl or C4-Cg cycloalkoxy(thiocarbonyl);
each R9 and R1 0 is independently H, -C7 alkyl, C}-C6 haloalkyl, C2-C6 alkenyl, C3-Cg alkynyl, C3-C^ cycloalkyl, C3-Cg halocycloalkyl, C2-C6
alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 (alkyl thio)carbonyl, C2-C6 alkoxy(thiocarbonyl), C4-C8 cycloalkylcarbonyl, C4-Cg cycloalkoxycarbonyl, C4-Cg (cycloalkylthio)carbonyl or C4-Cg cycloalkoxy(thiocarbonyl);
each n is independently 0, 1 or 2; and
(b) at least one additional fungicidal compound;
provided that component (a) is other than 4-chloro-5-(4-ethoxy-2,6- difluorophenyl)-2-methyl-l-(4-rnethylphenyl)-lH-irnidazole, 4-chloro-5-(4- ethoxy-2,6-difluorophenyl)--l -(4-fluorophenyl)-2--methyl-lH-imidazole, 4-[4- chloro- 1 -(3 ,4-difluorophenyl)-2-methyl- lH-imidazol-5-yl]- 3,5-difluorobenzonitrile or 4-[2-chloro-l -(4-chlorophenyl)-4-methyl-lH- imidazol-5-yl]-3,5-difluorobenzonitril6.
Figure imgf000004_0001
pyrimidinyl or benzyl, each optionally substituted with up to 3 substituents independently selected from R3 on carbon atom ring members and R4 on nitrogen atom ring members;
Q2 is phenyl, thienyl, thiazolyl, pyrazolyl, imidazolyl, pyndinyl, pyridazinyl,
pyrimidinyl or benzyl, each optionally substituted with up to 3 substituents independently selected from R5 on carbon atom ring members and R6 on nitrogen atom ring members; and
R1 and R2 are independently halogen, cyano, ethenyl, ethynyl, methoxy or
methylthio; or methyl optionally substituted with one substituent selected from halogen, -ΟΗ and methyl.
3. The composition of Claim 2 wherein in Formula 1,
Q1 is phenyl, pyridinyl or benzyl, each optionally substituted with up to 3
substituents independently selected from R3 on carbon atom ring members;
Q2 is phenyl, pyridinyl or benzyl, each optionally substituted with up to 3
substituents independently selected from R5 on carbon atom ring members; and
each R3 and R5 is independently halogen, cyano, C C3 alkyl, C2-C3 alkenyl, C2- C alkynyl, C1-C3 haloalkyl, cyclopropyl, C1-C3 alkoxy, Cj-C3 haloalkoxy, CrC3 alkylthio, C1-C3 alkylamino, C2-C4 dialkylamino, C2-C4
alkylcarbonyl, C2-C4 alkoxycarbonyl or C2-C4 alkylcarbonylamino.
4. The composition of Claim 3 wherein in Formula I,
Q1 is a phenyl or 3-pyridinyl ring optionally substituted with up to 3 substituents independently selected from R3 on carbon atom ring members; and
Q2 is a phenyl or 3-pyridinyl ring optionally substituted with up to 3 substituents independently selected from R5 on carbon atom ring members.
5. The composition of Claim 4 wherein in Formula 1,
R 1 and R2 are independently halogen, cyano or methoxy; or methyl optionally substituted with one substituent selected from F, CI or methyl; and each R3 and R5 is independently halogen, cyano, CrC3 alky I, C2-C3 alkenyl, Cr C3 haloalkyl, C1-C3 alkoxy, Cj^ haloalkoxy, C]-C3 alkylthio or C1-C3 alkylamino.
6. The composition of Claim 5 wherein in Formula 1,
R1 and R2 are independently CI, Br, I or C^C^ alkyl;
each R3 and R5 is independently F, CI, Br, cyano, C j-C2 alkyl, C | -C2 haloalkyl,
C1-C2 alkoxy or C1-C2 haloalkoxy; and
the ring of one of Q1 and Q2 is substituted with 2 or 3 substituents and the ring of the other of Q1 and Q2 is substituted with 1 or 2 substituents.
7. The composition of Claim 6 wherein in Formula 1,
R1 and R2 are independently CI, Br or methyl;
the ring of one of Q1 and Q2 is a phenyl or 3-pyridinyl ring substituted at a meta or para position with one substituent selected from F, CI, methyl, methoxy and fluoromethoxy, and optionally substituted with one F at a remaining position; and
the ring of the other of Q1 and Q2 is a phenyl ring substituted at both ortho
positions with F and substituted at a meta or para position with a substituent selected from cyano and. C^-C^ alkoxy.
8. The composition of Claim 1 wherein component (a) comprises a compound selected from the group consisting of
4-chloro-5-(2,6-difluoro-4-methoxyphenyl)-l -(3-fluorophenyl)-2-methyl- lH-imidazole,
3- [4-chloro-l -(4-chlorophenyl)-2-methyl-lH-imidazol-5-yl]-2,4- difluoiObenzonitrile,
2-bromo-l-(2,6-difluoro-4-methoxyphenyl)-5-(3-fluorophenyr)-4-methyl- 1 //-imidazole,
4- [2-chloro-l-(6-chloro-3-pyTidinyl)-4-methyl- lH-imidazol-5-yl]-
3 ,5-difluorobenzonitrile, 2-bromo-4-chloro-5-(4-ethoxy-2,6-difluorophenyl)-l-(3-fluorophenyl)-lH- imidazole,
4-chloro-5-(4-ethoxy-2,6-difluorophenyl)-l-(3-fluorophenyl)-2-methyl-lH- imidazole,
2-bromo-4-chloro- 1 - [ 3 - (difluoromethoxy)phenyl] -5 -(4- ethoxy-2, 6-difhiorophenyl)- lH-imidazole,
2,4-dicMoro-l -[3-(difluorometh.oxy)phenyl]-5-(4-ethoxy-2,6-difl iOTophenyl)- lH-imidazole,
4-[2-chloro- 1 -(6-methoxy-3 -pyridinyl)-4-methyl- lH-imidazol-5-yl]-
3 , -difluorobenzonitrile,
4-[2-bromo-l -(6-methoxy-3-pyridinyl)-4-methyl-lH-imidazoI-5-yl]-
3 , 5 -difluorobenzonitrile,
4- [2-bromo-4-chloro- 1 -(4-methylphenyl) - 1 H-imidazol - 5 -yl] -3 , 5 - difluorobenzonitrile,
4-chloro-l -[3-(difluoromethoxy)phenyl]-5-(4-ethoxy-2,6-difluorophenyl)-2- methyl- 1 H-rmidazole,
4-[2-bromo-4-chloro- 1 -(3-fluorophenyl)- lH-imidazol-5-yl]-3,5- difluorob enzonitrile,
4-[4-chloro-l-(3-fluorophenyl)-2-methyl-lH-imidazol-5-yl]-3,5- difluorobenzonitrile,
4-[2-bromo-4-chloro-l-(4-fluoTopherLyl)-lH-imidazol-5-yl]-3,5- difluorobenzonitrile,
2-chloro-l-[4-(difluoromethoxy)phenyl]-5-(2,6-difluoro-4-methoxyphenyl)-4- methyl- 1 //-imidazole,
4-[2-chloro-l-(3-fliiorophenyl)-4-metbyl-lH-imiclazol-5-yl]-3,5- difluorobcnzonitrile,
4-[4-chloro-l -(2,4-difluorophenyl)-2-methyl-lH-imidazol-5-yl]-
3 ,5-difluorobenzonitrile,
4-[2-chloro-l-[3-(difluoromethoxy)phenyl]-4-methyl-lH-imidazol-5-yl]-
3 ,5-difluorbbenzonitrile,
4-[2,4-dicMoro-l -[4-(difluoromet oxy)phenyl]-lH-imidazol-5-yl]-
3 ,5-difluorobenzonitrile, 4-[4-cUoro-l-(2-iluoro-4-methylphenyl)-2-methyl-lH-imidazol-5-yl]-
3,5-difluorobenzonitrile,
4-[4-bromo-l-(2-fIuoro-4-methylpheiiyl)-2-methyl-lH-imidazol-5-yl]-
3,5-difluorobenzonitrile, and
4-[2,4-dibromo-l -(3-fluorophenyl)-l^
9. The composition of any one of Claims 1 through 8 wherein component (b) includes at least one fungicide selected from the group consisting of:
(b 1 ) methyl benzimidazole carbamate fungicides;
(b2) dicarboxirnide fungicides;
(b3) dernethylation inhibitor fungicides;
(b4) phenylamide fungicides;
(b5) amine/morphoiine fungicides;
(b6) phospholipid biosynthesis inhibitor fungicides;
(b7) carboxamide fungicides;
(b8) hydroxy(2-amino-)pyrirnidine fungicides;
(b9) anilinopyrimidine fungicides;
(blO) N-phenyl carbamate fungicides;
(b l 1 ) quinone outside inhibitor fungicides;
(bl2) phenylpyrrole fungicides;
(bl3) quinoline fungicides;
(bl4) lipid peroxidation inhibitor fungicides;
(bl5) melanin biosynthesis inhibitors-reductase fungicides;
(bl6) melanin biosynthesis inhibitors-dehydratase fungicides;
(bl7) hydroxyanilide fungicides;
(bl8) squalene-epoxidase inhibitor fungicides;
bl ) polyoxin fungicides;
b20) phenylurea fungicides;
(b21) quinone inside inliibitor fungicides;
(b22) benzamide fungicides;
(b23) enopyranuronic acid antibiotic fungicides;
(b24) hexopyranosyl antibiotic fungicides;
b25) glucopyranosyl antibiotic: protein synthesis fungicides;
(b26) glucopyranosyl antibiotic: trehalase and inositol biosynthesis fungicides; (b27) cyanoacetamideoxime fungicides;
(b28) carbamate fungicides;
(b29) oxidative phosphorylation uncoupling fungicides;
(b30) organo tin fungicides;
(b31 ) carboxylic acid fungicides;
(b32) beteroaromatic fungicides;
(b33) phospbonate fungicides;
(b34) phthalamic acid fungicides;
(b35) benzotriazine fungicides;
(b36) benzene-sulfonamide fungicides;
(b37) pyridazinone fungicides;
(b38) thiophene-carboxamide fungicides;
(b39) pyrimidinamide fungicides;
(b40) carboxylic acid amide fungicides;
(b41) tetracycline antibiotic fungicides;
(b42) thiocarbamate fungicides;
(b46) fungicides other than fungicides of component (a) and components (bl) through (b45); and salts of compounds of (bl) through (b46).
10. The composition of Claim 9 wherein component (b) comprises at least one fungicide from each of two different groups selected from (bl) through (b4<5).
1 1. The composition of Claim 1 wherein component (b) includes at least one compound selected from acibenzolar-S-methyl, aldimorph, ametoctradin, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl, benalaxyl-M, benodanil, benomyl, benthiavalicarb, benthiavalicarb-isopropyl, bethoxazin, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, boscalid, bromuconazole, bupirimate, carboxin, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, cnlozolinate, clotrimazole, copper salts, cyazofamid, cyflufenaniid, cymoxanil, cyproconazole, cyprodinil, dichlofluanid, diclocymet, diclomezine, dicloran, diethofencarb, difenoconazole, diflumetorim, dimemirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinocap, dithianon, dodemorph, dodine, edifenphos, enestroburin, epoxiconazole, ethaboxam, ethirimol, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin,
fenpropimorph, fenpyrazamine, fentin acetate, fentin chloride, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, ilumetover, flumorph, fiuopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, fkitolanil, flutriafol, fhixapyroxad, folpet, fosetyl-aluminum, fuberidazole, furalaxyl, furametpyr, hexaconazole, hymexazol, guazatine, imazalil, imibenconazole, iminoctadine, iodocarb, ipconazole, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, maneb, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metconazole, methasulfocarb, metiram, metommostrobin, mepanipyrim, metrafenone, myclobutanil, naftifme, neo-asozin (ferric methanearsonate), nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxin, oxytetracycline, penconazole, pencycuron, penflufen, penthiopyrad, pefurazoate, phosphorous acid and salts, phthalide, picoxystrobin, piperalin, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propamocarb- hydrochloride, propiconazole, propineb, proquinazid, prothiocarb, prothioconazole, pyraclostrobin, pyrametostrobm, pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, pyrrolnitrin, quinomethionate, quinoxyfen, quintozene, sedaxane, silthiofam, simeconazole, spiroxarriine, streptomycin, s ilfur, tebuconazole, tebufloquin, tecloftalam, tecnazene, terbinafine, tetraconazole, thiabendazole, tliiiluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil, tolclofos- methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, triflumizole, tricyclazole, trifloxystrobin, triforine, trimorphamide, triticonazole, uniconazole, validamycin, valifenalate, vinclozolin, zineb, ziram, zoxamide, N-[4-[4- chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N- methylmethanimidamide, 5-chloro-6-(2,4,6-tTif]uorophenyl)-7-(4-methylpiperidin- 1 - yl)[l ,2,4]triazolo[l,5-a]pyrimidine, N-[2-[4-[[3-(4-cnlorophenyl)-2-propyn-l-yl]oxy]-3- memoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)aminojbutanarnide, N-[2-[4-[[3-(4- chlorophenyl)-2-propyn- 1 -yl] oxy] -3 -methoxyphenyl] ethyl] -3 -methyl-2-[(ethylsulfonyl)- amino]butanamide, 2-butoxy-6-iodo-3-propyl-4H-l-benzopyran-4-one, 3-[5-(4-chloro- phenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine, 4-fluorophenyl N-[ 1 -[[[ 1 -(4- cyai ophenyl)ethyl]sulfonyl]methyl]propyl]carbamate, N- [[(cycloprop ylmethoxy)amino] [6-(difluoromethoxy)-2,3 -difiuoro- phenyl]methylene]benzeneacetamide, a-(memoxyimino)-N-methyl-2- [ [ [ 1 - [3 -(triiluoro- mcdiyl)pheiiyl]ethoxy]imino]methyl]benzeneacetamide, N-[4-[4-chloro-3-(trifluoiO- methyl)phenoxy]-2,5~dimethylphenyl]-N-em^ jV-(4-chloro- 2-nitroplienyl)-N''-ethyl-4-methylbenzenesulfonamide, 2-[[[[3-(2,6-dichlorophenyl)-l- methyl-2-propen- 1 -ylidene]arnmo]oxy]methyl]-a-(niethoxyirrino)- N-memylbenzeneacetamide, 1 -[(2-propenylthio)carbonyl]-2-(l -methylethyl)-4-(2- methylphenyl)-5-amino- lH-pyrazol-3-one, 5-ethyl-6-octyl-[ 1 ,2,4]triazolo[ 1 ,5- a]pyriinidm-7-ylamine, pentyl N-[4-[[[[(l -methyl- lH-tetrazol-5-yl)phenylmcthylene]- amino]oxy]methyl]-2-thiazolyl]carbamate and pentyl N-[6-[[[[(l -methyl- lH-tetrazol-5- yl)plienylmethylene]ammo]oxy]methyl]-2-pyridinyl]carbamate.
12. A composition comprising:
(a) at least one compound selected from the, compounds of Formula 1 as defined in Claim 1 , N-oxides, and salts thereof; and at least one invertebrate pest control compound or agent,
13. A composition comprising the composition of any one of Claims 1 through 12 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.
14. A method for protecting a plant or plant seed from diseases caused by fungal pathogens comprisin applying a fungicidally effective amount of the composition of any one of Claims 1 through 13 to the plant or plant seed.
15. A method for protecting a plant from a Septoria disease comprising applying to the plant a fungicidally effective amount of the composition of any one of Claims 1 through 8 wherein component (b) includes at least one fungicidal compound selected from (b5) amine/morpholine fungicides.
16. A compound selected from the compounds of Formula 1 as defined in Claim 1, N-oxides, and salts thereof; pro vided that
when Q1 is phenyl, thienyl, thiazolyl, pyrazolyl, imidazolyl, pyridinyl,
pyridazinyl, pyrimidinyl, quiiiolinyl or benzyl, each optionally substituted with up to 4 substititents independently selected from R3a on carbon atom ring members and R4a on nitrogen atom ring members; wherein each R3a is independently halogen, cyano, hydroxy, nitro, Cj -C7 alkyl, C2- C7 alkenyl, C2-C7 alkynyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C^CJQ alkyl cycloalkyl, C4-CJO cycloalkylalkyl, Cg-C^ cycloalkylcycloalkyl, C3-C7 cycloalkoxy, C3-C7 halocycloalkoxy, C1-C7 alkoxy, C1-C7 haloalkoxy, C1-C alkylthio, C]-C haloalkylthio, C j -C7 alkylsulflnyl, C j -C7 alkylsulfonyl, C } -C7
haloalkylsulfinyl, CrC7 haloalkylsulfonyl, C C7 alkylamino, C2-C7 dialkylamino, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C2-C7 alkylcarbonylamino, C3-C10 trialkylsilyl, -SCN, C(=S)NH2 or -X-U-Z; and each R4a is independently cyano, Cj-C^ alkyl, C3-Cg alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C2-C6 alkoxyalkyl, Co-C^ alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminoalkyl or C3-C5 dialkylaminoalkyl;
then Q2 is phenyl, thienyl, thiazolyl, pyrazolyl, imidazolyl, pyridinyl, pyridazinyl, pyrimidinyl, quinolinyl or benzyl, each substituted with 1 to 4 substituents independently selected from R5 on carbon atom ring members and R6 on nitrogen atom ring members; provided that least one substituent is C2-C7 cyanoalkyl, C2-C7 cyanoalkoxy, aminocarbonyl, C2-C7 alkylaminocarbonyl or C3-C7 dialkylaminocarbonyl on a carbon atom ring member, or C1-Cg haloalkyl on a nitrogen atom ring member.
PCT/US2010/053679 2009-11-04 2010-10-22 Fungicidal mixtures WO2011056463A2 (en)

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