DK2403834T3 - Fungicide pyrazoler - Google Patents

Fungicide pyrazoler Download PDF

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DK2403834T3
DK2403834T3 DK10707187.0T DK10707187T DK2403834T3 DK 2403834 T3 DK2403834 T3 DK 2403834T3 DK 10707187 T DK10707187 T DK 10707187T DK 2403834 T3 DK2403834 T3 DK 2403834T3
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dimethyl
pyrazol
oxy
alkyl
dichloro
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Jeffrey Keith Long
Andrew Edmund Taggi
Wonpyo Hong
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Du Pont
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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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
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  • Engineering & Computer Science (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (2)

FUNGICIDE PYRAZOLER
1 hvor Q1 er en phenylring eller et naphthalenylringsystem, hvor hver ring eller ringsystem eventuelt er substitueret med op til 5 substituenter uafhængigt udvalgt fra R3; eller en 5- til 6-leddet fuldt umættet heterocyklisk ring eller et 8- til 1 O-leddet heteroaromatisk bicyklisk ringsystem, hvor hver ring eller ringsystem indeholder ringdele udvalgt fra carbonatomer og op til 4 heteroatomer uafhængigt udvalgt fra op til 2 O-, op til 2 S- og op til 4 N-atomer, hvor op til 3 carbonringdele er uafhængigt udvalgt fra C(=0) og C(=S), og svovlatomringdelene er uafhængigt udvalgt fra S(=0)u(=NR14)v, hvor hver ring eller ringsystem eventuelt er substitueret med op til 5 substituenter uafhængigt udvalgt fra R3 på carbonatomringdele og udvalgt fra cyan, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Q-Q-alkoxy, C2-C6-alkoxyalkyl, C2-Cg-alkylcarbonyl, C2-Cg-alkoxycarbonyl, C2-C6-alkylaminoalkyl og C3-Cg-dialkylaminoalkyl på nitrogenatomringdele; Q2 er en phenylring eller et naphthalenylringsystem, hvor hver ring eller ringsystem eventuelt er substitueret med op til 5 substituenter uafhængigt udvalgt fra R3; eller en 5- til 6-leddet mættet, delvist umættet eller fuldt umættet heterocyklisk ring eller et 8- til 10-leddet heteroaromatisk bicyklisk ringsystem, hvor hver ring eller ringsystem indeholder ringdele udvalgt fra carbonatomer og op til 4 heteroatomer uafhængigt udvalgt fra op til 2 O-, op til 2 S- og op til 4 N-atomer, hvor op til 3 carbonringdele er uafhængigt udvalgt fra C(=0) og C(=S), og svovlatomringdelene er uafhængigt udvalgt fra S(=0)u(=NR14)v, hvor hver ring eller ringsystem eventuelt er substitueret med op til 5 substituenter uafhængigt udvalgt fra R3 på carbonatomringdele og udvalgt fra cyan, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, C2-C6-alkoxyalkyl, C2-C6-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylaminoalkyl og C3-C6-dialkylaminoalkyl på nitrogenatomringdele; eller Ci-Ci2-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl, C3-Ci2-cycloalkyl eller C3-Ci2-cycloalkenyl, hvor hver eventuelt er substitueret med op til 5 substituenter uafhængigt udvalgt fra R3; XerO, S(0)m eller NR4; R1 er H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C7-cycloalkyl, C02R5, C(0)NR6R7, cyan, Q-Q-alkoxy, Ci-C6-haloalkoxy eller C2-C5-alkoxyalkyl; eller R1 er phenyl eventuelt substitueret med op til 3 R8; eller en fem- eller seks-leddet nitrogenindeholdende aromatisk heterocyklus eventuelt substitueret med op til 3 substituenter uafhængigt udvalgt fra R9a på carbonatomringdele og R9b på nitrogenatomringdele; Rla er H; eller Rla og R1 er taget sammen med det carbonatom, hvortil de er bundet, for at danne en cyclopropylring eventuelt substitueret med op til 2 substituenter uafhængigt udvalgt fra halogen og methyl; R2 er CH3, CH2CH3, halogen, cyan, cyanmethyl, halomethyl, hydroxymethyl, methoxy eller methylthio; eller cyclopropyl eventuelt substitueret med op til 2 substituenter uafhængigt udvalgt fra halogen og methyl; hver R3 er uafhængigt udvalgt fra halogen, cyan, amino, methylamino, dimethylamino, formylamino, C2-C3-alkylcarbonylamino, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C3-alkoxy, CrC3-haloalkoxy, Ci-C3-alkylthio, Ci-C3-haloalkylthio, Ci-C3-alkylsulfinyl, Ci-C3-haloalkylsulfmyl, Ci-C3-alkylsulfonyl, Cr C3-haloalkylsulfonyl, Ci-C2-alkylsulfonyloxy, Ci-C2-haloalkylsulfonyloxy, C3-C4-cycloalkyl, C3-C7 cycloalkoxy, C4-C6-alkylcycloalkyl, C4-C6-cycloalkylalkyl, C3-C7-halocycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, hydroxy, formyl, C2-C3-alkylcarbonyl, C2-C3-alkylcarbonyloxy, -SF5, -SCN, C(=S)NR19R20 og -U-V-T; R4 er H, formyl, C2-C5-alkenyl, C3-C5-alkynyl, C3-C7-cycloalkyl, -S03M+, -S(=0)tR10, -(C=W)Rn, NH2 eller OR21; eller Ci-C6-alkyl eller Ci-C6-haloalkyl, hver eventuelt substitueret med op til 2 R12; R5 er H, Ci-Cg-alkyl eller Ci-Cg-haloalkyl; R6 og R7 er uafhængigt udvalgt fra H, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C7-cycloalkyl, C4-C8-cycloalkylalkyl og C4-C8-alkylcycloalkyl; eller R6 og R7 er taget sammen med det nitrogenatom, hvortil de er bundet, for at danne en fire- til syv-leddet nonaromatisk heterocyklisk ring indeholdende ringdele, ud over det forbindende ringnitrogenatom, udvalgt fra carbonatomer og eventuelt op til én ringdel udvalgt fra O, S(0)n og NR13; hver R8, R9a og R9b er uafhængigt udvalgt fra halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, cyan, nitro, SCH3, S(0)CH3 og S(0)2CH3; R10 er Ci-C^-alkyl eller Ci-Q-haloalkyl; R11 er Ci-C6-alkyl, Ci-C6-alkoxy, C2-C7-alkoxyalkyl, C2-C7-alkylaminoalkyl, C3-C8-dialkylaminoalkyl, Ci-C6-alkylthio eller C2-C7-alkylthioalkyl; hver R12 er uafhængigt C3-C7-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl eller cyan; R13 er H, Ci-C3-alkyl eller C2-C3-haloalkyl; hver R14 er uafhængigt H, cyan, Ci-C3-alkyl eller Ci-C3-haloalkyl; hver R19 og R20 er uafhængigt H eller CH3; R21 er H, formyl, C3-C7-cycloalkyl, -S03"M+ eller -(C=W)Rn; eller Q-Q-alkyl eller Ci-C6-haloalkyl, hver eventuelt substitueret med op til 2 R12; hver U er uafhængigt O, S(=0)w, NR22 eller en direkte binding; hver V er uafhængigt Q-Q-alkylen, C2-C6-alkenylen, C3-C6-alkynylen, C3-C6-cycloalkylen eller C3-C6-cycloalkenylene, hvor op til 3 carbonatomer er uafhængigt udvalgt fra C(=0), hver eventuelt substitueret med op til 5 substituenter uafhængigt udvalgt fra halogen, cyan, nitro, hydroxy, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy og Ci-C6-haloalkoxy; hver T er uafhængigt cyan, NR23aR23b, OR24 eller S(=0)yR25; hver R22 er uafhængigt H, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-(alkylthio)carbonyl, C2-C6-alkoxy(thiocarbonyl), C4-C8-cycloalkylcarbonyl, C4-C8-cycloalkoxycarbonyl, C4-C8-(cycloalkylthio)carbonyl eller C4-C8-cycloalkoxy(thiocarbonyl); hver R23a og R23b er uafhængigt H, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6-alkoxy(thiocarbonyl), C4-C8-cycloalkylcarbonyl, C4-C8-cycloalkoxycarbonyl, C4-C8-(cycloalkylthio)carbonyl eller C4-C8-cycloalkoxy(thiocarbonyl); eller et par af R23a og R23b forbundet til det samme nitrogenatom er taget sammen med nitrogenatomet for at danne en 3- til 6-leddet heterocyklisk ring, hvilken ring eventuelt er substitueret med op til 5 substituenter uafhængigt udvalgt fra R26; hver R24 og R25 er uafhængigt H, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6-alkoxy(thiocarbonyl), C4-C8-cycloalkylcarbonyl, C4-C8-cycloalkoxycarbonyl, C4-C8-(cycloalkylthio)carbonyl eller C4-C8-cycloalkoxy(thiocarbonyl); hver R26 er uafhængigt halogen, CrQ-alkyl, Ci-C6-haloalkyl eller Ci-C6-alkoxy; W er O eller S; M+ er en kation; m er 0, 1 eller 2; n er 0, 1 eller 2; t er 0, 1 eller 2; hver u og v er uafhængigt 0, 1 eller 2 i hvert tilfælde af S(=0)u(=NR14)v, under forudsætning af at summen af u og v er 0, 1 eller 2; hver w er uafhængigt 0, 1 eller 2; og hver y er uafhængigt 0, 1 eller 2; under forudsætning af: når Q2 er en phenylring substitueret på mindst én orthoposition med en substituent, der er udvalgt fra -U-V-T, hvor U er en direkte binding, V er C(=0) og T er NR23aR23b eller OR24, så er X andet end NR4; og under forudsætning af at forbindelsen med formlen 1 er andet end: (a) 2,4-dichlor-5-{[l,3-dimethyl-4-(3-methyl-l,2,4-oxadiazol-5-yl)-l//-pyrazol-5-yl]oxy}phenol; (b) 2,4-dichlor-5-{[l,3-dimethyl-4-(5-methyl-l,3,4-thiadiazol-2-yl)-l//-pyrazol-5-yl]oxy}phenol; (c)
(d) 2-(l,3-dimethyl-4-phenylpyrazolyl)amino-2-imidazolin HC1; (e) methyl(25)-2-(2,4-dichlor-5-{[4-(isoxazol-3-yl)-l,3-dimethyl-lF/-pyrazol-5- yl]oxy}phenoxy)propionat; (f) (25)-2-(2,4-dichlor-5-{[4-(iso xazol-3-yl)-l, 3-dimethyl-177-pyrazol-5-yl]oxy}phenoxy)propionsyre; (g) methyl (25)-2-[2,4-dichlor-5-({4-[5-(hydroxymethyl)isoxazol-3-yl]-l,3-dimethyl-177- pyrazol-5-yl}oxy)phenoxy]propionat; (h) (25)-2-[2,4-dichlor-5-({4-[5-(hydroxymethyl)isoxazol-3-yl]-l,3-dimethyl-177-pyrazol-5-yl} oxy)phenoxy]propionsyre; (i) methyl (25)-2-(2,4-dichlor-5- {[ 1,3 -dimethyl-4-(5-methylisoxazol-3 -yl)- 177-pyrazol-5 - yl]oxy}phenoxy)propionat; (j) (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(5-methylisoxazol-3-yl)-177-pyrazol-5-yl]oxy}phenoxy)propionsyre; (k) methyl (25)-2-[2,4-dichlor-5-( {4-[5-( 1 -hydroxy-1 -methylethyl)isoxazol-3 -yl] -1,3- dimethyl-177-pyrazol-5-yl}oxy)phenoxy]propionat; (l) (25)-2-[2,4-dichlor-5-( {4-[5-( 1 -hydroxy-1 -methylethyl)isoxazol-3 -yl] -1,3 -dimethyl-1H-pyrazol-5 -yl} oxy)phenoxy]propionsyre; (m) (25)-2-(2,4-dichlor-5-{[ l,3-dimethyl-4-(3-methyl-l,2,4-oxadiazol-5-yl)-177-pyrazol-5-yl]oxy}phenoxy)propionsyre; (n) methyl (25)-2-(2,4-dichlor-5-{[l, 3-dimethyl-4-(3-methyl-1,2,·4-oxadiazol-5-yl)-177- pyrazol-5 -yl] oxy} phenoxy)propionat; (o) (25)-2-(2,4-dichlor-5-{[ l,3-dimethyl-4-(5-methyl-l,3,4-thiadiazol-2-yl)-177-pyrazol-5-yl]oxy}phenoxy)propionsyre; eller (p) methyl (25)-2-(2,4-dichlor-5-{[ l,3-dimethyl-4-(5-methyl-l,3,4-thiadiazol-2-yl)-177- pyrazol-5 -yl] oxy} phenoxy)propionat.
2. Forbindelse med formlen 1, hvor: Q1 er phenyl, pyridinyl, pyrimidinyl, pyrazinyl eller pyridazinyl, hver substitueret med fra 1 til 4 substituenter uafhængigt udvalgt fra R3; under forudsætning af at når en R3-substituent er placeret ved en metaposition, så er R3-substituenten udvalgt fra F, Cl, Br og cyan; Q2 er phenyl, pyridinyl, pyrimidinyl, pyrazinyl eller pyridazinyl, hver substitueret med 1, 2 eller 3 substituenter uafhængigt udvalgt fra R3, under forudsætning af at når en R3-substituent er placeret ved en metaposition, så er R3-substituenten udvalgt fra F, Cl, Br og cyan; X er O eller NR4; R1 er H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C02R5, C(0)NR6R7, cyan, Ci-C6-alkoxy, Ci-C6-haloalkoxy eller C2-C5-alkoxyalkyl; Rla er H; R2 er CH3, CH2CH3, Cl eller Br; hver R3 er uafhængigt udvalgt fra halogen, cyan, amino, methylamino, dimethylamino, C1-C4-alkyl, Ci-Czphaloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy Ci-C3-alkylthio, Ci-C3-haloalkylthio, Ci-C3- alkylsulfinyl, Ci-C3-haloalkylsulfinyl, Ci-C3-alkylsulfonyl, Ci-C3-haloalkylsulfonyl, C3-C4-cycloalkyl, C(=S)NH2 og -U-V-T; R4 er H, formyl, C3-C7-cycloalkyl eller -SR10; eller Ci-C6-alkyl eller Ci-C6-haloalkyl, hver eventuelt substitueret med op til 2 R12; R5 er Ci-C6-alkyl; R6 er H eller Ci-Ci-alkyl; R7 er H, Ci-Ci-alkyl, Ci-C6-haloalkyl eller CzpCg-alkylcycloalkyl; eller R6 og R7 er taget sammen med det nitrogenatom, hvortil de er bundet, for at danne en fire- til syv-leddet nonaromatisk heterocyklisk ring indeholdende ringdele, ud over det forbindende nitrogenatom, udvalgt fra carbonatomer og op til én ringdel udvalgt fra O og NR13; hver R12 er uafhængigt C3-C7-cycloalkyl, Ci-C4-alkoxy eller cyan; og R13 er H eller CH3.
3. Forbindelse med formlen 2, hvor Q1 er phenyl eller pyridinyl, hver substitueret med 1, 2 eller 3 substituenter uafhængigt udvalgt fra R3; Q2 er phenyl eller pyridinyl, hver substitueret med 1, 2 eller 3 substituenter uafhængigt udvalgt fra R3; R1 er H, halogen eller Ci-C6-alkyl; R2 er CH3, Cl eller Br; hver R3 er uafhængigt udvalgt fra halogen, cyan, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy og -U-V-T; R4 er H, formyl, C3-C7-cycloalkyl eller -SR10; eller Ci-C6-alkyl substitueret med én R12; R12 er cyclopropyl, -OCH3 eller cyan; hver U er uafhængigt O eller NH; hver V er uafhængigt C2-C4-alkylen; hver T er uafhængigt NR23aR23b eller OR24; hver R23a og R23b er uafhængigt H, Ci-C6-alkyl eller Ci-C6-haloalkyl; og hver R24 er uafhængigt H, Ci-Ci-alkyl eller Ci-C6-haloalkyl.
4. Forbindelse med formlen 3, hvor mindst én af Q1 og Q2 er phenyl substitueret med 2 eller 3 substituenter uafhængigt udvalgt fra R3; R1 er H eller CH3; R2 er CH3; R4 er H; hver R3 er uafhængigt udvalgt fra halogen, cyan, Ci-C3-alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy og Ci -C3 -haloalkoxy.
5. Forbindelse med formlen 4, hvor Q1 er phenyl substitueret ved 2-, 4- og 6-positionerne med substituenter uafhængigt udvalgt fra R3; eller phenyl substitueret ved 2- og 4-positioneme med substituenter uafhængigt udvalgt fra R3; eller phenyl substitueret ved 2- og 6-positioneme med substituenter uafhængigt udvalgt fra R3; Q2 er phenyl substitueret ved 2-, 4- og 6-positionerne med substituenter uafhængigt udvalgt fra R3; eller phenyl substitueret ved 2- og 4-positioneme med substituenter uafhængigt udvalgt fra R3; eller phenyl substitueret ved 2- og 6-positioneme med substituenter uafhængigt udvalgt fra R3; R1 er H; og hver R3 er uafhængigt udvalgt fra F, Cl, Br, cyan, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy og Ci-C2-haloalkoxy.
6. Forbindelse med formlen 5, hvor hver R3 er uafhængigt udvalgt fra F, Cl, Br, cyan, methyl, Ci-C2-alkoxy og fluormethoxy.
7. Forbindelse med formlen 6, hvor X er O eller NH; og hver R3 er uafhængigt udvalgt fra F, Cl, Br, cyan og methoxy.
8. Forbindelse med formlen 1, hvor Rla er H; Q1 og Q2 er uafhængigt phenyl, thienyl, pyridinyl, pyridazinyl, pyrazinyl eller pyrimidinyl, hver eventuelt substitueret med op til 5 substituenter uafhængigt udvalgt fra R3; XerO, S(0)m eller NR4; R1 er H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C7-cycloalkyl, C02R5, C(0)NR6R7, cyan, Ci-C6-alkoxy, Ci-C6-haloalkoxy eller C2-C5-alkoxyalkyl; eller R1 er phenyl eventuelt substitueret med op til 3 R8; eller en fem- eller seks-leddet nitrogenindeholdende aromatisk heterocyklus eventuelt substitueret med op til 3 substituenter uafhængigt udvalgt fra R9a på carbonatomringdele og R9b på nitrogenatomringdele; R2 er CF13, CF12CF[3, cyclopropyl eller halogen; hver R3 er uafhængigt udvalgt fra halogen, cyan, amino, methylamino, dimethylamino, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkylthio, Ci-C3-haloalkylthio, C1-C3-alkylsulfinyl, Ci-C3-haloalkylsulfinyl, Ci-C3-alkylsulfonyl, Ci-C3-haloalkylsulfonyl, C3-C4-cycloalkyl, C3-C7-cycloalkoxy, C4-C6-alkylcycloalkyl, C4-C6-cycloalkylalkyl, C3-C7-halocycloalkyl, C2-C4-alkenyl og C2-C4-alkynyl; R4 er H, formyl, C3-C7-cycloalkyl, -S03M+, -SR10 eller -(C=W)Rn; eller Q-Q-alkyl eller CrC6-haloalkyl, hver eventuelt substitueret med op til 2 R12; R5 er H, Q-Q-alkyl eller Ci-C6-haloalkyl; R6 og R7 er uafhængigt udvalgt fra H, Q-Q-alkyl, Ci-C6-haloalkyl, C3-C7-cycloalkyl, C4-C8-cycloalkylalkyl og C4-C8-alkylcycloalkyl; eller R6 og R7 er taget sammen med det nitrogenatom, hvortil de er bundet, for at danne en fire- til syv-leddet nonaromatisk heterocyklisk ring indeholdende ringdele, ud over det forbindende ringnitrogenatom, udvalgt fra carbonatomer og eventuelt op til én ringdel udvalgt fra O, S(0)n og NR13; hver R8, R9a og R9b er uafhængigt udvalgt fra halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, cyan, nitro, SCH3, S(0)CH3 og S(0)2CH3; R10 er Ci-Ci-alkyl eller Ci-Ci-haloalkyl; R11 er Ci-Ci-alkyl, Ci-C6-alkoxy, C2-C7-alkoxyalkyl, C2-C7-alkylaminoalkyl, C3-C8-dialkylaminoalkyl, Ci-C6-alkylthio eller C2-C7-alkylthioalkyl; hver R12 er uafhængigt C3-C7-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfmyl eller CrC4-alkylsulfonyl; R13 er H, Ci-C3-alkyl eller C2-C3-haloalkyl; W er O eller S; M+ er en kation; m er 0, 1 eller 2; og n er 0, 1 eller 2.
9. Forbindelse med formlen 8, hvor Q1 er phenyl, pyridinyl, pyrimidinyl, pyrazinyl eller pyridazinyl, hver substitueret med fra 1 til 4 substituenter uafhængigt udvalgt fra R3; Q2 er phenyl, pyridinyl, pyrimidinyl, pyrazinyl eller pyridazinyl, hver substitueret med 1, 2 eller 3 substituenter uafhængigt udvalgt fra R3 X er O eller NR4; R1 er H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C02R5, C(0)NR6R7, cyan, Ci-C6-alkoxy, Ci-C6-haloalkoxy eller C2-C5-alkoxyalkyl; eller R1 er en fem- eller seks-leddet nitrogen-indeholdende aromatisk heterocyklus eventuelt substitueret med op til 3 substituenter uafhængigt udvalgt fra R9a på carbonatomringdele og R9b på nitrogenatomringdele; R2 er CH3, CH2CH3, Cl eller Br; hver R3 er uafhængigt udvalgt fra halogen, cyan, amino, methylamino, dimethylamino, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy Ci-C3-alkylthio, Ci-C3-haloalkylthio, Ci-C3-alkylsulfmyl, Ci-C3-haloalkylsulfmyl, Ci-C3-alkylsulfonyl, Ci-C3-haloalkylsulfonyl og C3-C4-cycloalkyl; R4 er H, formyl, C3-C7-cycloalkyl eller -SR10; eller Ci-C6-alkyl eller Ci-C6-haloalkyl, hver eventuelt substitueret med op til 2 R12; R5 er H eller Ci-Cg-alkyl; R6 er H eller Ci-Ci-alkyl; R7 er H, Ci-C6-alkyl, Ci-C6-haloalkyl eller C4-C8-alkylcycloalkyl; eller R6 og R7 er taget sammen med det nitrogenatom, hvortil de er bundet, for at danne en fire- til syv-leddet nonaromatisk heterocyklisk ring indeholdende ringdele, ud over det forbindende nitrogenatom, udvalgt fra carbonatomer og op til en ringdel udvalgt fra O og NR13; hver R9a er uafhængigt udvalgt fra halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, cyan og nitro; hver R9b er CrC2-alkyl; R10 er CH3, CH2CH3, CF3 eller CF2CF3; hver R12 er uafhængigt C3-C7-cycloalkyl eller Ci-C4-alkoxy; og R13 er H eller CH3.
10. Forbindelse med formlen 8 eller 9, hvor Q1 er phenyl eller pyridinyl, hver substitueret med 1, 2 eller 3 substituenter uafhængigt udvalgt fra R3; Q2 er phenyl eller pyridinyl, hver substitueret med 1, 2 eller 3 substituenter uafhængigt udvalgt fra R3; X er NR4; R1 er H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, cyan, Ci-C6-alkoxy eller Ci-C6-haloalkoxy; R2 er CH3; hver R3 er uafhængigt udvalgt fra halogen, cyan, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C3-alkoxy og Ci -C3 -haloalkoxy; R4 er H, formyl, C3-C7-cycloalkyl eller -SR10; eller Ci-C6-alkyl substitueret med én R12; R10 er CH3; og R12 er cyclopropyl eller -OCH3.
11. Forbindelse med formlen 1, hvor Q1 er phenyl substitueret ved 2- og 4-positionerne med substituenter uafhængigt udvalgt fra R3; Q2 er phenyl substitueret ved 2- og 6-positionerne med substituenter uafhængigt udvalgt fra R3; X er NR4; R1 er H; Rla er H; R2 er CH3; hver R3 er uafhængigt udvalgt fra F, Cl, Br og cyan; og R4 er H.
12. Forbindelse med formlen 1, der er udvalgt fra gruppen: 4-(2-chlor-4-fhiorphenyl)-l,3-dimethyl-lV-(2,4,6-trifluorphenyl)-l.i/-pyrazol-5-amin, iV-(4-chlorphenyl)-4-(2,6-difluor-4-methoxyphenyl)-l,3-dimethyl-l//-pyrazol-5-amin, 4-(2,6-difluor-4-methoxyphenyl)-A/-(2,4-difluorphenyl)-l,3-dimethyl-lF/-pyrazol-5-amin, 4-(2,6-difluor-4-methoxyphenyl)-l,3-dimethyl-#-(2,4,6-trifluorphenyl)-lF/-pyrazol-5-amin, lV-(2,6-difluor-4-methoxyphenyl)-4-(3,4-difluorphenyl)-1,3 -dimethyl- lF/-pyrazol-5 -amin, 4-(2,4-difluorphenyl)-l,3-dimethyl-#-(2,4,6-trifluorphenyl)-lF/-pyrazol-5-amin, 4-[[4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lF/-pyrazol-5-yl]oxy]-3,5-difluorbenzonitril, 4-[[4-(2,6-difluorphenyl)-l,3-dimethyl-lF/-pyrazol-5-yl]oxy]-3-fluorbenzonitril, 4-(2-chlor-4-fluorphenyl)-#-(2,6-difluorphenyl)-l,3-dimethyl-lF/-pyrazol-5-amin, 4-[[4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lF/-pyrazol-5-yl]oxy]-3-fluorbenzonitril, 3-chlor-4-[[4-(2,6-difluorphenyl)-l,3-dimethyl-lF/-pyrazol-5-yl]oxy]benzonitril, A^,4-bis(2-chlor-4-fluorphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, iV-(2-chlor-4-fluorphenyl)-4-(2-chlor-6-fluorphenyl)-1,3 -dimethyl- l//-pyrazol-5 -amin, A/-(2-chlor-4,6-difluorphenyl)-4-(2,6-difluorphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, #-(2-chlor-4,6-difluorphenyl)-4-(2,4-difluorphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, ,/V-(4-chlor-2,6-difluorphenyl)-4-(2,6-difluorphenyl)-l,3-dimethyl-l//-pyrazol-5-amin, #-(4-chlor-2,6-difluorphenyl)-4-(2,4-difluorphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, 3- chlor-4-[[4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-l//-pyrazol-5-yl]oxy]benzonitril, 4- [[4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-l/i-pyrazol-5-yl]amino]-3,5-difluor-benzonitril, 4-[[4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-l//-pyrazol-5-yl]oxy]-2,5-difluor-benzonitril, A/-(2-chlor-4-fluorphenyl)-4-(2,6-difluor-4-methoxyphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, Ar-(4-chlor-2,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-l/i-pyrazole-5-amin, A^-(2-chlor-4,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-l//-pyrazol-5-amin, #-(2,6-dichlor-4-fluorphenyl)-4-(2,4-difluorphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, 3-chlor-4-[5-[(2-chlor-4,6-difluorphenyl)amino]-l,3-dimethyl-l//-pyrazol-4-yl]-benzonitril, 3- chlor-4-[5-[(4-chlor-2,6-difluorphenyl)amino]-l,3-dimethyl-l//-pyrazol-4-yl]-benzonitril, A^-(2-brom-4-fluorphenyl)-4-(2,4-difluorphenyl)-l,3-dimethyl-l//-pyrazol-5-amin, 4- (2-chlor-4-fluorphenyl)-Ar-(2,4-dichlor-6-fluorphenyl)-l,3-dimethyl-l/i-pyrazol-5-amin, 4-(2-chlor-4-fluorphenyl)-A^-(2,6-dichlor-4-fluorphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, 4-[[4-(2-brom-4-fluorphenyl)-l,3-dimethyl-l//-pyrazol-5-yl]oxy]-3-fluorbenzonitril, iV-(2-brom-4-fluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-l/i-pyrazol-5-amm, 4-(2-brom-4-fluorphenyl)-1,3 -dimethyl-iV-(2,4,6-trifluorphenyl)- l//-pyrazol-5 -amin, Af-(4-brom-2,6-difluorphenyl)-4-(2,4-difluorphenyl)-1,3 -dimethyl- l//-pyrazol-5 -amin, 4-[[4-(2-brom-4-fluorphenyl)-l,3-dimethyl-l//-pyrazol-5-yl]oxy]-3,5-difluor-benzonitril, 4-(2 -brom-4-fluorphenyl)-iV-(2-chlor-4,6-difluorphenyl)-1,3 -dimethyl-177-pyrazol-5-amin, 4-(2 -brom-4-fluorphenyl)-iV-(4-chlor-2,6-difluorphenyl)-1,3 -dimethyl-177-pyrazol-5-amin, iV-(4-brom-2,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-l//-pyrazol-5-amin, 3-brom-4-[[4-(2,4-difluorphenyl)-l,3-dimethyl-l//-pyrazol-5-yl]oxy]benzonitril, 3- chlor-4-[[4-(2,4-difhiorphenyl)-l,3-dimethyl-177-pyrazol-5-yl]oxy]benzonitril, iV-(2,4-dichlor-6-fluorphenyl)-4-(2,4-difluorphenyl)-l,3-dimethyl-l//-pyrazol-5-amin, #-(2,6-dichlor-4-fluorphenyl)-4-(2,6-difluorphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, Af-(2-brom-4,6-difluorphenyl)-4-(2,4-difluorphenyl)-1,3 -dimethyl- l//-pyrazol-5 -amin, iV-(2-brom-4,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-l//-pyrazol-5-amin, #-(4-brom-2,6-difluorphenyl)-4-(2,6-difluorphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, #-(2-brom-4,6-difluorphenyl)-4-(2,6-difluorphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, #-(2-brom-4,6-difluorphenyl)-4-(2-chlor-6-fluorphenyl)-l,3-dimethyl-l_i/-pyrazol-5-amin, 4- [5-[(2-chlor-4,6-difluorphenyl)amino]-l,3-dimethyl-l_i/-pyrazol-4-yl]-3-fluorbenzonitril, og 4-[5-[(4-chlor-2,6-difhiorphenyl)amino]-l,3-dimethyl-l//-pyrazol-4-yl]-3-fhrorbenzonitril.
13. Forbindelse ifølge krav 1, der er 4-(2,6-difhior-4-methoxyphenyl)-l,3-dimethyl-lV-(2,4,6-trifluorphenyl)- l//-pyrazol-5-amin.
14. Fungicidsammensætning, der omfatter (a) en forbindelse ifølge et hvilket som helst af kravene 1 til 13 eller en forbindelse udvalgt fra 2,4-dichlor-5-{[l,3-dimethyl-4-(3-methyl-l,2,4-oxadiazol-5-yl)-l//-pyrazol-5-yl]oxy}phenol; 2,4-dichlor-5-{[l,3-dimethyl-4-(5-methyl-l,3,4-thiadiazol-2-yl)-lF/-pyrazol-5-yl]oxy}phenol;
2-(l,3-dimethyl-4-phenylpyrazolyl)amino-2-imidazolin HC1; methyl (25)-2-(2,4-dichlor-5-{[4-(isoxazol-3-yl)-l,3-dimethyl-l//-pyrazol-5-yl]oxy}phenoxy)propionat; (25)-2-(2,4-dichlor-5-{[4-(isoxazol- 3-yl)-l,3-dimethyl-l//-pyrazol-5-yl]oxy[phenoxy)propionsyre; methyl(25)-2-[2,4-dichlor-5-({4-[5- (hydroxymethyl)isoxazol-3-yl]-l,3-dimethyl-l//-pyrazol-5-yl}oxy)phenoxy]propionat; (25)-2-[2,4-dichlor- 5-( {4-[5-(hydroxymethyl)isoxazol-3 -yl] -1,3 -dimethyl- l//-pyrazol-5-yl} oxy)phenoxy]propionsyre; methyl (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(5-methylisoxazol-3-yl)-l//-pyrazol-5-yl]oxy}phenoxy)propionat; (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(5-methylisoxazol-3-yl)-l//-pyrazol-5-yl]oxy[phenoxy)propionsyre; methyl (25)-2-[2,4-dichlor-5-({4-[5-(l-hydroxy-l-methylethyl)isoxazol-3-yl]-l,3-dimethyl-lF/-pyrazol-5-yl}oxy)phenoxy]propionat; (25)-2-[2,4-dichlor-5-({4-[5-(l-hydroxy-1-methylethyl)isoxazol-3-yl]-l,3-dimethyl- l//-pyrazol-5 -yl} oxy)phenoxy]propionsyre; (25)-2-(2,4-dichlor-5- {[ 1,3 -dimethyl-4-(3 -methyl- l,2,4-oxadiazol-5-yl)-l//-pyrazol-5-yl]oxy}phenoxy)propionsyre; methyl (25)-2-(2,4-dichlor-5-{[ 1,3-dimethyl-4-(3 -methyl-1,2,4-oxadiazol-5-yl)- l//-pyrazol-5-yl]oxy}phenoxy)propionat; (25)-2-(2,4-dichlor- 5-{[ 1,3-dimethyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)-l//-pyrazol-5-yl]oxy}phenoxy)propionsyre; og methyl (25)-2-(2,4-dichlor-5-{[ 1,3 -dimethyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)-lF/-pyrazol-5 -yl]oxy}phenoxy)propionat og (b) mindst ét andet fungicid.
15. Sammensætning ifølge krav 14, hvor bestanddel (b) er udvalgt fra prothioconazol, metconazol, penthiopyrad og chlorthalonil.
16. Fungicidsammensætning, der omfatter: (a) en forbindelse ifølge et hvilket som helst af kravene 1 til 13; og (b) mindst én yderligere bestanddel udvalgt fra gruppen bestående af overfladeaktive midler, faste fortyndingsmidler og flydende fortyndingsmidler.
17. Fremgangsmåde til bekæmpelse af plantesygdomme forårsaget af svampeplantepatogener, der omfatter påføring til planten eller en del deraf, eller til plantefrøet, af en fungicidt effektiv mængde af en forbindelse ifølge et hvilket som helst af kravene 1 til 13 eller en forbindelse udvalgt fra 2,4-dichlor-5-{[l,3-dimethyl-4-(3-methyl-l,2,4-oxadiazol-5-yl)-17/-pyrazol-5-yl]oxy}phenol; 2,4-dichlor-5-{[l,3- dimethyl-4-(5-methyl-l,3,4-thiadiazol-2-yl)-lT/-pyrazol-5-yl]oxy}phenol;
2-(1,3-dimethyl-4-phenylpyrazolyl)amino-2-imidazolin HC1; methyl (25)-2-(2,4-dichlor-5-{[4-(isoxazol-3-yl)-l,3-dimethyl-l.i/-pyrazol-5-yl]oxy}phenoxy)propionat; (25)-2-(2,4-dichlor-5-{[4-(isoxazol- 3-yl)-l,3-dimethyl-l//-pyrazol-5-yl]oxy}phenoxy)propionsyre; methyl (25)-2-[2,4-dichlor-5-({4-[5-(hydroxymethyl)isoxazol-3-yl]-l,3-dimethyl-l//-pyrazol-5-yl}oxy)phenoxy]propionat; (25)-2-[2,4-dichlor- 5-( {4-[5-(hydroxymethyl)isoxazol-3 -yl] -1,3 -dimethyl- l//-pyrazol-5-yl} oxy)phenoxy]propionsyre; methyl (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(5-methylisoxazol-3-yl)-l.i/-pyrazol-5-yl]oxy}phenoxy)propionat; (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(5-methylisoxazol-3-yl)-l//-pyrazol-5- yl]oxy}phenoxy)propionsyre; methyl (25)-2-[2,4-dichlor-5-({4-[5-(l-hydroxy-1-methylethyl)isoxazol-3-yl]-l,3-dimethyl-l//-pyrazol-5-yl}oxy)phenoxy]propionat; (25)-2-[2,4-dichlor-5-({4-[5-(l-hydroxy-l- methylethyl)isoxazol-3 -yl] -1,3 -dimethyl- l//-pyrazol-5-yl} oxy)phenoxy]propionsyre; (25)-2-(2,4-dichlor-5 -{[l,3-dimethyl-4-(3-methyl-l,2,4-oxadiazol-5-yl)-l//-pyrazol-5-yl]oxy}phenoxy)propionsyre; methyl (25)- 2- (2,4-dichlor-5-{[l,3-dimethyl-4-(3-methyl-l,2,4-oxadiazol-5-yl)-l//-pyrazol-5- yl]oxy}phenoxy)propionat; (25)-2-(2,4-dichlor-5-{[l, 3-dimethyl-4-(5-methyl-1,3,·4-thiadiazol-2 -y\)AH- pyrazol-5-yl]oxy}phenoxy)propionsyre; og methyl (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(5-methyl-l,3,4-thiadiazol-2-yl)-l//-pyrazol-5-yl]oxy}phenoxy)propionat.
18. Sammensætning, der omfatter en forbindelse ifølge et hvilket som helst af kravene 1 til 13 eller en forbindelse udvalgt fra 2,4-dichlor-5- {[ 1,3 -dimethyl-4-(3 -methyl-1,2,4-oxadiazol-5-yl)- l//-pyrazol-5 -yl]oxy (phenol; 2,4-dichlor-5- {[ 1,3 -dimethyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)- l//-pyrazol-5 - yl]oxy}phenol;
1. Forbindelse udvalgt fra formel 1, A-oxider og salte deraf,
2-(l,3-dimethyl-4-phenylpyrazolyl)amino-2-imidazolin HC1; methyl (25)-2-(2,4-dichlor-5-{[4-(isoxazol-3-yl)-l,3-dimethyl-l//-pyrazol-5-yl]oxy}phenoxy)propionat; (25)-2-(2,4-dichlor-5-{[4-(isoxazol- 3- yl)-l,3-dimethyl-l//-pyrazol-5-yl]oxy}phenoxy)propionsyre; methyl (25)-2-[2,4-dichlor-5-({4-[5-(hydroxymethyl)isoxazol-3-yl]-l,3-dimethyl-l//-pyrazol-5-yl}oxy)phenoxy]propionat; (25)-2-[2,4-dichlor-5-( {4-[5-(hydroxymethyl)isoxazol-3 -yl] -1,3 -dimethyl- l//-pyrazol-5-yl} oxy)phenoxy]propionsyre; methyl (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(5-methylisoxazol-3-yl)-l//-pyrazol-5-yl]oxy}phenoxy)propionat; (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(5-methylisoxazol-3-yl)-l//-pyrazol-5- yl]oxy}phenoxy)propionsyre; methyl (25)-2-[2,4-dichlor-5-({4-[5-(l-hydroxy-l-methylethyl)isoxazol-3-yl]-l,3-dimethyl-l//-pyrazol-5-yl}oxy)phenoxy]propionat; (25)-2-[2,4-dichlor-5-({4-[5-(l-hydroxy-l-methylethyl)isoxazol-3-yl]-1,3-dimethyl-l//-pyrazol-5-yl}oxy)phenoxy]propionsyre; (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(3-methyl-l,2,4-oxadiazol-5-yl)-l//-pyrazol-5-yl]oxy}phenoxy)propionsyre; methyl (25)- 2-(2,4-dichlor-5-{[l,3-dimethyl-4-(3-methyl-l,2,4-oxadiazol-5-yl)-l//-pyrazol-5- yl]oxy}phenoxy)propionat; (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)-l//-pyrazol-5-yl]oxy}phenoxy)propionsyre; og methyl (25)-2-(2,4-dichlor-5-{[l,3-dimethyl-4-(5-methyl-l,3,4-thiadiazol-2-yl)-l//-pyrazol-5-yl]oxy}phenoxy)propionat og mindst én forbindelse eller ét middel til bekæmpelse af hvirvelløse skadedyr.
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