OA11299A - Pesticidal 1-arylpyrazoles - Google Patents

Pesticidal 1-arylpyrazoles Download PDF

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Publication number
OA11299A
OA11299A OA9900143A OA9900143A OA11299A OA 11299 A OA11299 A OA 11299A OA 9900143 A OA9900143 A OA 9900143A OA 9900143 A OA9900143 A OA 9900143A OA 11299 A OA11299 A OA 11299A
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Prior art keywords
phenyl
trifluoromethyl
pyrazole
dichloro
alkyl
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OA9900143A
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English (en)
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Patrick Doyle Lowder
David Treadway Manning
Peter Wyatt Newsome
Jenniver Lantz Phillips
Nicholas Charles Ray
Tai-Teh Wu
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Rhone Poulenc Agrochimie
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    • 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
    • C07D231/38—Nitrogen atoms
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • 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
    • 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
    • C07D231/44—Oxygen and nitrogen or sulfur and 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (12)

  1. What is claimed is: A compound having the formula:
    N
    R Z N N
    R, 5 wherein: X is -S(O)mRô or R7, Y is hvdrogen, C-3 to C-6 alkenyl, alkynyl, formyl, alkylcarbonvl. cvcloalkylcarbonyl. halocycloalkyl carbonyl, aroyk arylalkvlcarbonyl,alkylsulfonyl, arylsulfonyl, haloalkylcarbonyl, aminoalkylcarbonyl,alkylaminoalkylcarbonyl. dialkylaminoalkylcarbonvl, alkoxyalkylcarbonyl,arvloxyalkylcarbonyl, alkylthioalkylcarbonyl, alkylsulfonylalkvlcarbonyl.arylthioalkylcarbonvl, N-alkylcarbamoyl, N-arylcarbamoyl, N-alkylthiocarbamoyl,N-arylthiocarbamoyl, alpha-hydroxyarylalkylcarbonyl. hvdroxyalkylcarbonyl.carboxyalkylcarbonyl, alkoxycarbonylalkylcarbonyl, -P(=O)(O-Alkyl)2,-P(=S)(O-aIkyl)2, -P(=O)(S-alkyl)2, -P(=S)(S-alkyl)2, trialkylsilvl,alkylcarbonylaminoalkylcarbonyl, alkylcarbonyloxyalkylcarbonyl, aryl,pyridinyl, pyrimidinyl, -C(=O)S-alkyl, -C(=O)S-aryl, -C(=O)S-alkylaryl,alkoxyalkoxycarbonyl, alkylthioalkoxy carbonyl, alkylsulfonylalkoxycarbonyl,arvlthioalkoxycarbonyl, alkoxycarbonyl, aryloxvcarbonyl and aryloxycarbonylalkylcarbonyl; or alkyl or haloalkyl both of which areunsubstituted or substituted by alkoxy, alkoxycarbonyl, carboxy. cyano,aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthio, nitro,alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, amino. alkylamino. dialkylamino,hvdroxy, alkylcarbonylamino or alkylcarbonyloxy; Z is hydrogen, halogen, -C(O)R7-,-S(O)nRg, -C(O)OR9, alkyl, haloalkyl, -OR9,-N=C(Rio)(Ri 1), alkenyl, hydrazino, alkylthiocarbonyl, 1 H-pyrrol-1 -yl orlH-pyrazol-l-yl, -CHO, -CH=NOH, amino, R^NH-or R43R14N-; -js- ο i ns 9 R] is hydrogen, alkyl or-NRi5Rl6-R2 is hydrogen or halogen; R3 and R5 are hydrogen, halogen or alkyl; R4 is halogen. haloalkyl, haloalkoxy, R]7S(O)p-or SF5; 5 R6 is alkyl or haloalkyl, alkenyl or haloalkenyl. alkynyl or haloalkynvl or cvcloalkylhaving 3 to 5 carbon atoms; R7 is alkyl or haloalkyl; R8 is R7 or phenyl; R9 and Rio are hydrogen, alkyl or haloalkyl; 10 Rl 1 is alkyl, haloalkyl, alkoxy, or a phenyl group which is unsubstituted or substituted by one or more groups selected from hydroxy, halogen. alkoxy, 1 cvano, R7 or -S(O)qR7; Rjo, R-13 and Rl4, which are identical or different, are R7S(O)r-. formyl, alkynyl, 15 alkoxycarbonyl, alkylthiocarbonyl or aroyl; or alkyl, C-3 to C-6 alkenyl or -C(O)alkyl wherein the alkyl and alkenyl portions are unsubstituted orsubstituted by one or more Rig;or Rl3 and R14 are joined so as together form a divalent radical having 4 to 6 atoms inthe chain, this divalent radical being alkylene, alkyleneoxyalkylene or 20 alkyleneaminoalkylene; Rl5 and Ri5 are independentlv hydrogen or alkyl; Rl7 is haloalkyl; Rlg is cvano, nitro, alkoxy, haloalkoxy, -C(O)R7, RgS(O)s-, -C(O)OR9. aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, halogen, hydroxy, 25 aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl; m, n, p. q. r and s are i'ndependent of one another zéro, one or two; M is C-halo, C-CH3, C-CH2F, C-CH2CI, C-NO2, or N; or a géométrie isomer, tautomeric form or pesticidally active sait thereof. 30
  2. 2. A compound of formula (I) according to Claim 1, in which: X is -SfO)mRô; Y is hydrogen; alkyl having 1 to 4 carbon atoms, cycloalkyl having up to 4 carbonsboth of which are unsubstituted or substituted by aminocarbonyl,alkylsulfonyl, alkoxy, alkoxycarbonyl, alkylcarbonyl, cyano or nitro; C-3 to C- 35 4 alkenyl; C-3 to C-5 alkynyl; alkylcarbonyl; unsubstituted or substituted aroyl; arylalkylcarbonyl; alkylsulfonyl; alkoxycarbonylalkylcarbonyl; haloalkylcarbonyl; N-alkylcarbamoyl; alkoxycarbonyl; aryloxycarbonyl; GÏ'Î2>9 alkoxyalkylcarbonvl; alpha-hydroxyarylalkvlcarbonyl; hydroxyalkylcarbonyl; aminoalkylcarbonvl: -C(=O)S-alkyl and trialkylsilyl; Z is amino. R12NH-, R13R14N-. halogen or methyl; Rl is hvdrogen, methyl, amino or methylamino; R2 is F, Cl. Br or H: R3 and R5 are hvdrogen; R4 is CF3. CF3O, CHFo, CF3S(O)p? CF2CI. CFCI2 . CF2CIO. CFCbO. Cl. Br. or F;Rô is methyl or ethyl optionally substituted by F, Cl or Br; Mis CCI, CF, CBr, or N; Rj2, R13 and R14 are CF3S(O)r-, alkynyl or alkoxycarbonyl; or alkyl, C-3 to C-6 alkenyl or -C(O)alkyl wherein the alkyl and alkenyl portions are unsubstitutedor substituted by one or more Rl g; and Rl 8 is cvano, nitro. alkoxy. haloalkoxy, -C(O)R7, RgS(O)s-, -C(O)OR9, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, halogen, hydroxy,aminosulfonyl, alkylaminosulfonvl or dialkylaminosulfonyl.
  3. 3-Acetyl-5-amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl--ΙΗ-pyrazole oxime;
    3. The compound of formula (I) according to Claim 1 or Claim 2. whichis:
  4. 4. A pesticidal composition comprising:
    wherein: X is -S(O)mR6 or R-7, Y is hydrogen, C-3 to C-6 alkenvl, alkynyl, formyl, alkylcarbonyl, aroyl,arylalkylcarbonvl, alkylsulfonyl, arylsulfonyl, haloalkylcarbonyl,aminoalkylcarbonyl. alkylaminoalkylcarbonyl, dialkylaminoalkylcarbonyl.alkoxyalkylcarbonyl, aryloxyalkylcarbonyl, alkylthioalkylcarbonyl,alkylsulfonylalkvlcarbonyl, arylthioalkylcarbonyl, N-alkyicarbamoyl,N-arylcarbamovl, N-alkylthiocarbamoyl, N-arylthiocarbamoyl, alpha-hydroxyarylalkylcarbonyl, hvdroxyalkylcarbonyl, carboxyalkylcarbonyl,alkoxycarbonylalkylcarbonyl, -P(=O)(O-Alkyl)2, -P(=S)(O-alkyl)2,-P(=O)(S-alkyl)2, -P(=S)(S-alkyl)2, trialkylsilyl, — δ’ι-' alkylcarbonvlaminoalkylcarbonyl. alkylcarbonvloxyalkylcarbonyl. aryl.pyridinyl, pyrimidinyl. -C(=O)S-alkyl. -C(=O)S-arvl. -C(=O)S-alkvlaryl.alkoxyalkoxvcarbonyl, alkylthioalkoxvcarbonyl. alkylsulfonylalkoxycarbonyl.arylthioalkoxycarbonvl, alkoxvcarbonyl. aryloxvcarbonvl and 5 aryloxycarbonylalkylcarbonyl; or alkyI or haloalkvl both of which are unsubstituted or substituted by alkoxy, alkoxycarbonyl, carboxy. cyano,aminocarbonyl, alkylaminocarbonyl. dialkvlaminocarbonyl. alkylthio, nitro,alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, amino, alkylamino, dialkylamino.hydroxy, alkyicarbonylamino or alkylcarbonyloxy; 10 Z is hvdrogen. halogen, -C(O)R7-,-S(O)nRg, -C(O)OR9, alkyl, haloalkvl. -ORç,-N^C(Riq)(Ri 1), alkenyl, hydrazino, alkylthiocarbonyl, IH-pyrrol-l-yl or I· lH-pyrazol-l-yl, -CHO, -CH=NOH, amino, R^NH-or R13R14N-; Rl is hvdrogen, alkyl or-NR]5Ri6; R2 is hvdrogen or halogen; 15 R3 and R5 are hydrogen, halogen or alkyl; R4 is halogen, haloalkyl, haloalkoxy, Ri7S(O)p-or SF5; Rô is alkyl or haloalkvl, alkenyl or haloalkenyl, alkynyl or haloalkynyl or cvcloalkylhaving 3 to 5 carbon atoms; R7 is alkyl or haloalkyl; 20 Rg is R7 or phenyl; R9 and Rio are hydrogen, alkyl or haloalkyl; Rl 1 is alkyl, haloalkyl, alkoxy, or a phenyl group which is unsubstituted or substituted by one or more groups selected from hydroxy, halogen. alkoxy.cyano, R7 or 25 -S(O)qR7; R12, Rl3 and R14, which are identical or different, are R7S(O)r-, formyl, alkynyl,alkoxycarbonyl, alkylthiocarbonyl or aroyl; or alkyl, C-3 to C-6 alkenyl or-C(O)alkyl wherein the alkyl and alkenyl portions are unsubstituted orsubstituted by one or more Ri g;or 30 Rl 3 and R14 are joined so as together form a divalent radical having 4 to 6 atoms inthe chain, this divalent radical being alkylene, alkyleneoxyalkylene oralkyleneaminoalkylene; Rl5 and Ri6 are independently hydrogen or alkyl; Rl7 is haloalkyl; 35 Rjg is cyano, nitro. alkoxy. haloalkoxy. -C(O)R7, RgS(O)s-, -C(O)OR9, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl. halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl; -Θ1- m. n. p. q. r and s are independent of one another zéro, one or two: M is C-halo. C-CH3. C-CFbF. C-CPbCl. C-NO2. or N; or a géométrie isomer. tautomeric form or pesticidally active sait thereof: and(b) an agriculturallv acceptable inert carrier therefor.
  5. 5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(tertbutyloxycarbonvlamino)-1 H-pyrazole carboximidamide;
    5-Amino-1 -[2.6-dichloro-4-(trifluoromethyl)phenyI]-4-methylsuIfïnyl-N-( 1.1-dimethylpropyloxycarbonvlamino)-1 H-pyrazole carboximidamide; or
    5-Amino-l-[2?6-dichloro-4-(trifluoromethyI)phenyl]-4-methylsulfinyl-N-(n-propoxycarbonylamino)-1 H-pyrazole carboximidamide;
    5-Amino-1 - [2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(tridecvlcarbonylamino)-1 H-pyrazole carboximidamide;
    5-Amino-1- [2.6-dichloro-4-(trifIuoromethy l)pheny l]-4-methylsulfinyl-N-chloroacetylamino-1 H-pyrazole carboximidamide;
    5-Amino- l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfînyl-N-acetylamino-1 H-pyrazole carboximidamide;
    5-Amino-1-[2,6-dichIoro-4-(trifluoromethyl)phenyl]-4-methylsulfïnyi-N-(hexylcarbonylamino)-1 H-pyrazole carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)pheny]]-4-methylsulfïnyl-N-(pentylcarbonylamino)-l H-pyrazole carboximidamide:
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyI]-4-methylsulfmyl-N-(butylcarbonylamino)-1 H-pyrazole carboximidamide;
    5-Amino-1 -[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-( 1 -ethylpropylcarbonylamino)-l H-pyrazole carboximidamide:
    5-Amino-1 -[2.6-dichloro-4-( trifluoromethyl)phenyl]-4-methylsuIfinyi-N-(propylcarbonylamino)-1 H-pyrazole carboximidamide:
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(ethylcarbonylamino)-l H-pyrazole carboximidamide;
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(2-35 methylethenylcarbonylamino)-lH-pyrazole carboximidamide;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmyl-N-(terÎ-butylcarbonyiamino)-l H-pyrazole carboximidamide;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(l-methylethenylcarbonylamino)-l H-pyrazole carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylsulfinyl-N-acetylamino-1 H-pyrazole carboximidamide;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinyl-N-amino-lH-pyrazole carboximidamide;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylsulfinyl-N-25 amino-lH-pyrazole carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmyl-N-(ethoxycarbonyl)amino-1 H-pyrazole-3-carboximidamide;
    5-Amino-1-[2,6-dÎchloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(n-heptylcarbonyl)amino-1 H-pyrazole-3-carboximidamide;
    5-Amino- l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(isopropylcarbonyl)amino-1 H-pyrazole-3-carboximidamide;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmyl-N-amino-1H-pyrazole-3-carboximidamide;
    5-Amino-1-12,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-trif!uoromethylsulfenyl-lH-pyrazole-3-carboximidamide.
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-trifluoro10 methylsulfonyl-lH-pyrazole-3-carboximidamide; or
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsuifinyl-N-[(3-acetyioxy)phenyIcarbonyloxy]-lH-pyrazole carboximidamide;
    5-Amino-1 -[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-( 1 -ethylpropyicarbonyIoxv)-lH-pyrazoie carboximidamide;
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(bromoacetyloxy)-l H-pyrazole carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsullinyl-N-(chloroacetvloxy)-l H-pyrazole carboximidamide:
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmyl-N-(iso-propylcarbonyloxy) -1 H-pyrazole carboximidamide; 35 l-[2.6-Dichloro-4-(trifluoromethyI)phenyI]-5-formylamino-4-ethylsulfinyl-N-(acetyioxy)-1 H-pyrazole carboximidamide; ‘ ! " ' i i • > i i ... y -(3^-
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyI)phenyl]-4-methylsulfinyl-N-(tert-butylcarbonyloxy) -1 H-pyrazole carboximidamide;
    5-Amino-1 -[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-30 (cyclopentylcarbonyloxy) -1 H-pyrazole carboximidamide;
    5-Amino- l-[2,6-dichloro-4-(trifluoromethyI)phenyl]-4-methylsulfenyl-N-(cyclopentylcarbonyloxy) -1 H-pyrazole carboximidamide;
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmyl-N- (butylcarbonyloxy) -1 H-pyrazole carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(pentylcarbonyloxv) -1 H-pyrazole carboximidamide;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(hexvlcarbonyloxy) -1 H-pyrazole carboximidamide;
    5-Amino-l-(2.6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylsulfmyl-N-(acetyloxy)-1 H-pyrazole carboximidamide; l-[2.6-Dichloro-4-(trifluoromethyl)phenyl]-5-formylamino-4-ethylsulfenyl-N-20 (acetvloxy)-1 H-pyrazole carboximidamide;
    5-Amino-1 -[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfenyl-N- (heptvlcarbonyloxy) -1 H-pyrazole carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfenyl-N-(acetyloXy)1 H-pyrazole carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfonyl-N-(heptylcarbonyloxy) -1 H-pyrazole carboximidamide;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-10 (heptylcarbonyloxy) -1 H-pyrazole carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfonyl-N-(acetyloxy)1 H-pyrazole carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-(benzoyloxy) -ΙΗ-pyrazole carboximidamide: 5 l-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-methylamino-4-methylsulfinyl-N-(acetyioxy)-1 H-pyrazole carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmyl-N-(2-methylethenylcarbonvloxy) -1 H-pyrazole carboximidamide:
    5-Amino-1 - [2,6-dichloro-4-(trifluoromethy l)phenyl]-4-methylsulfinyl-N-(propylcarbonyioxy) - ΙΗ-pyrazole carboximidamide;
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-rnethylsulfînyl-N-(ethylcarbonyloxy) - ΙΗ-pyrazole carboximidamide;
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinyl-N-(acetyloxy) -ΙΗ-pyrazole carboximidamide;
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsuifinyl-N-(acetyloxy) -ΙΗ-pyrazole carboximidamide;
    5. A method for the control of pests at a locus comprising applying tosaid locus a pesticidally effective amount of a compound of formula (I)
    wherein: X is -S(O)mR6 or R7, Y is hvdrogen. C-3 to C-6 alkenyl. alkynvl, formyl, alkylcarbonyl. aroyl.arylalkylcarbonyl. alkylsulfonyl, arylsulfonyl, haloalkylcarbonyl.aminoalkylcarbonyl, alkylaminoalkylcarbonyl, dialkylaminoalkylcarbonyl.alkoxyalkylcarbonyl, aryloxyalkylcarbonyl, alkylthioalkylcarbonyl,alkylsulfonylalkylcarbonyl, arylthioalkylcarbonyl, N-alkylcarbamoyl.N-arylcarbamoyl, N-alkylthiocarbamoyl, N-arylthiocarbamoyl, alpha-hydroxyarylalkylcarbonyl, hydroxyalkylcarbonyl, carboxyalkylcarbonyl,alkoxycarbonylalkylcarbonyl, -P(=O)(O-Alkyl)2, -P(=S)(O-alkyl)2,-P(=O)(S-alkyI)2, -P(=S)(S-alkyl)2, trialkylsilyl, alkylcarbonvlaminoalkylcarbonyl, alkylcarbonyloxyalkylcarbonyl, aryl,pvridinyl, pyrimidinyl, -C(=O)S-alkyl, -C(=O)S-aryl, -C(=O)S-alkylaryl,alkoxyalkoxycarbonyl, alkylthioalkoxycarbonyl, alkylsulfonylalkoxycarbonyl,arylthioalkoxycarbonyk alkoxycarbonyl, aryloxycarbonyl andaryloxycarbonvlalkylcarbonyl; or alkyl or haloalkyl both of which areunsubstituted or substituted by alkoxy, alkoxycarbonyl, carboxy, cyano,aminocarbonyl. alkylaminocarbonyl, dialkylaminocarbonyl, alkylthio, nitro, -ffS- i, i alkvlsulfinyl. alkylsulfonyl. alkylcarbonyl. amino. alkylamino. dialkylamino.hydroxy. alkvlcarbonylamino or alkylcarbonvloxy: Z is hydrogen. halogen, -C(O)R7-.-S(O)nRg. -C(O)OR9. alkyl. haloalkyl, -ORç. -N=C(R]o)(Rl l)- alkenyl. hydrazino. alkvlthiocarbonyl. ΙΗ-ρνσοΜ-yl orlH-pyrazol-l-yl, -CHO, -CH=NOH. amino. R^NH-or R13R14N-; Rl is hydrogen. alkyl or-NRi5Ri6; R2 is hydrogen or halogen; R3 and R5 are hydrogen, halogen or alkyl; R4 is halogen. haloalkyl, haloalkoxy, R}7S(O)p-or SF5; Rô is alkyl or haloalkyl, alkenyl or haloalkenyl. alkynyl or haloalkynvl or cycloalkvlhaving 3 to 5 carbon atoms; R7 is alkyl or haloalkyl; R8 is R7 or phenyl; R9 and Rio are hydrogen, alkyl or haloalkyl; Rl 1 is alkyl, haloalkyl, alkoxy, or a phenyl group which is unsubstituted or substituted bv one or more groups selected from hydroxy. halogen, alkoxy.cvano, R7 or -S(O)qR7; Rl2- Rl3 and R14, which are identical or different, are R7S(O)r-, formyl, alkynyl.alkoxvcarbonyl, alkylthiocarbonvl or arovl; or alkyl. C-3 to C-6 alkenyl or-C(O)alkyl wherein the alkyl and alkenyl portions are unsubstituted orsubstituted by one or more Rl8;or Rl3 and R14 are joined so as together form a divalent radical having 4 to 6 atoms inthe chain, this divalent radical being alkvlene, alkyleneoxyalkylene oralkyleneaminoalkylene; Rl5 and R] 6 are independently hydrogen or alkyl; Rl7 is haloalkyl; Rl8 is cyano, nitro, alkoxy, haloalkoxy, -C(O)R7. RsS(O)s-, -C(O)OR9, aminocarbonvl. alkylaminocarbonvl, dialkylaminocarbonyl, halogen. hydroxy,aminosulfonyl, alkylaminosulfonvl or dialkylaminosulfonyl; m. n, p. q. r and s are independent of one another zéro, one or two; M is C-halo, C-CH3, C-CH2F, C-CH2CI. C-NOo, or N; or a géométrie isomer, tautomeric form or pesticidally active sait thereof.
    5-Amino-l-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-methylsulfinyl-N- hydroxy-lH-pyrazole-3-carboximidamide; l-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-5-methylamino-4- methylsulfmyl-lH-pyrazole-3-carboximidamide; 20 l-[2?6-Dichloro-4-(trifluoromethyl)phenyl]-5-ethylamino-N-hydroxy-4- methylsulfinyl-1 H-pyrazole-3-carboximidamide; l-[2.6-Dichloro-4-(trifluoromethyl)phenyl]-5-[2-(ethylsulfonyl)ethylamino]N-hydroxy-4-methylsulfmyl-1 H-pyrazole-3-carboximidamide:5-[2-(Cyano)ethylamino]-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-25 hydroxy-4-methylsulfinyl-lH-pyrazole-3-carboximidamide; 5-(Aminocarbdnylmethylammo)-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]N-hydroxy-4-methy lsulfmy 1-1 H-py razole-3-carboximidamide;l-[2,6-Dichloro-4-(trifluoromethyl)phenyI]-4-rnethylsulfmyl-5-[2-(phenylsulfonyl)ethylamino]-N-hydroxy-lH-pyrazole-3-carboximidamide;30 5-Amino-l-[2.6-dibromo-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N- hydroxy-1 H-pyrazole-3-carboximidamide; l-[2-Bromo-6-chloro-4-(trifluoromethyl)phenyl]-5-ethvlamino-4-methylsulfinyl-N-hydroxy-lH-pyrazole-3-carboximidamide;5-Amino-l-[2-bromo-6-chloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl·5 lH-pyrazole-3-carboximidamide; l-[2.6-Dichloro-4-('trifluoromethyl)phenyl]-4-ethylsulfinyl-5-[2- (methylsulfmyl')ethylamino]-N-hydroxy-lH-pyrazole-3-carboxirnidamide; l-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsuifinyl-5-[2- (methylsulfinyl)ethylamino]-N-hydroxy-lH-pyrazole-3-carboximidamide; l-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinyl-5-[2-(ethylsulfmyl)ethylamino]-N-hydroxy-lH-pyrazole-3-carboximidamide;l-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-5-[(prop-2-vnyl)amino]-N-hydroxy-l H-pyrazole-3-carboximidamide; and5-Amino-l-[2-chloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-hydroxy1 H-pyrazole-3'Carboximidamide.
    5- Amino-l-[2.6-dichloro-4-(trifluoromethyI)phenyl]-N-hydroxy-4-[2-(fluoroethyl)sulfonyl]-lH-pyrazole-3-carboximidamide;5-Amino-l-[3-chIoro-5-(trifluoromethyl)-2-pyridinyl]-4-ethylsulfinyl-N- 15 hydroxv-1 H-pyrazole-3-carboximidamide;
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4- [2-(fluoroethyl)sulfmyl]-lH-pyrazole-3-carboximidamide;
    5-Arnino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-methoxy-N'-methyl· 4- methylsulfinyl-lH-pyrazole-3-carboximidamide;
    5-Amino-l-[2,6-dichloro-4“(trifluoromethyl)pheriyl]-N-methoxy-4- methylsulfinyl-lH-pyrazoIe-3-carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-ethyl- 5 sulfonvl-1 H-pyrazole-3-carboximidamide;
    5-Amino-l-[2.6-dichioro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-methyl-thio-1 H-pyrazole-3-carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-methyl- ; i _ .· > sulfonvl-lH-pyrazole-3-carboximidamide:
    5-Amino-1 -[2.6-dichloro-4-(trifluoromethoxy)phenyl]-N-hydroxy-4-methy 1-sulfmyl-lH-pyrazole-3-carboximidamide;
    5-Amibo-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-methyl-sulfinyl-1 H-pyrazole-3-carboximidamide;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-ethylthio-1 H-pyrazole-3-carboximidamide;
    5-Amino-1 -[2.6-dichloro-4-(trifluoromethyI)phenyl]-N-hydroxy-4-ethylsulfmyl-lH-pyrazole-3-carboximidamide;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-methoxy-4-trifluoro-methylsulfinyl-lH-pyrazole-3-carboximidamide;
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-trifluoro- methylsulfinyl-lH-pyrazole-3-carboximidamide;
    5-Amino-1 -[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethy 1-1H-pyrazole-3-carboxaldehyde oxime;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethoxy)phenyl]-4-ethylsulfinyl-lH-pyrazole-3-carboxaldehyde oxime;
    5-Amino-l-[3-chloro-5-(trifluoromethyl)-2-pyridinyI]-4-methylsulfinyl-lH-pyrazole-3-carboxaldehyde oxime; 1 -[2.6-Dichloro-4-(trifluoromethyl)phenyi]-4-ethylthio-5-methyl-1 H-pyrazole- 3-carboxaldehyde oxime; 1 -[2.6-Dichloro-4-(trifluoromerhyl)phenyl]-4-ethylsulfinyl-5-methyl-1H-pyrazole-3-carboxaldehyde oxime; l-[2-Chloro-4-(trifluoromethyl)phenyl]-5-[2-(ethylsulfonyl)ethylamino]-4-methylsulfinyl-1 H-pyrazole-3-carboxaldehyde oxime;l-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-dimethylamino-4-methylthio-1 H-pyrazole-3-carboxaldehyde oxime;
    5-Amino-1 -[2.6-dichloro-4-( trifiuoromethyl)phenyI]-4-methylsulfiny 1-1H-pyrazole-3-carboxaldehyde O-(2-cyanoethyl)oxime:l-[2.6-Dichloro-4-(trifluoromethyl)phenyl]-5-methyI-4-methylthio-lH-pyrazole-3-carboxaldehyde oxime; 1 -[2.6-Dichloro-4-(trifluoromethyI)phenyl]-5-methyl-4-methylsulfinyl-1 H-pyrazole-3-carboxaldehyde oxime; 1 -[2.6-Dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-methy lsulfonyl-1H-pyrazole-3-carboxaldehyde oxime;
    5-Amino-1 -[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmvl-1H- pyrazole-3-carboxaldehyde O-[2-(ethylsulfonyl)ethyl]oxime;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H- pyrazole-3-carboxaldehyde O-(aminocarbonylmethyl)oxime;
    5-Amino-1 -[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(ethoxycarbonylmethyl)oxime;
    5-Amino- l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfiny 1-1H-pyrazole-3-carboxaldehyde O-(tert-butyldimethylsilyl)oxime; 25 l-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-formyl-N-hydroxy-4- trifluoromethyrthio-1 H-pyrazole-3-carboximidamide;l-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-5-hydroxyiminomethyl-4-trifluoromethylthio-lH-pyrazole-3-carboximidamide5-Amino-1 -[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsuIfmyl- 1H- 30 pyrazole-3-carboxaldehyde O-(isopropyl)oxime;
    5-Amino-1 -[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmy 1-1H- 20 pyrazole-3-carboxaldehyde O-(carboxymethvl)oxime; 1 -[2.6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1 H-pvrazole-3-carboxaldehyde oxime;
    5-Amino-1 -[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmy 1-1H-pyrazole-3-carboxaldehyde O-(N-methylcarbamoyl)oxime;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-lH- pyrazole-3-carboxaldehyde O-(methyl)oxime;
    5-Amino-1-[2.6-dichloro-4-(îrifluoromethyl)phenyl]-4-methylsulfonyl-lH-pyrazole-3-carboxaldehyde oxime;
    5-Amino-1 -[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylthio-1H-pyrazoie-3-carboxaldehyde O-(methoxycarbonyl)oxime;
    5-Amino-1 -[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmyl-1H-pyrazole-3-carboxaldehyde O-[2-(ethoxycarbonyl)propionyl]oxime;5-Amino-1 -[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylthio-1H- 10 pyrazole-3-carboxaldehyde O-(acetyl)oxime;
    5-Amino-l-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-lH- pyrazole-3-carboxaldehyde O-(methoxycarbonyl)oxime;
    5-Amino-1-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(2-methylbenzovl)oxime:
    5-Amino-l-[2.6-dichIoro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-lH-pyrazole-3-carboxaldehyde O-(acetyl)oxime;
    5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylthio-1 H-pyrazoie-3-carboxaldehyde O-(methyl)oxime;
    5-Amino-1 -[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylthio-1H-pyrazole-3-carboxaldehyde oxime:
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-difluoromethylthio-l H-pyrazole-3-carboxaldehyde oxime;
    5-Amino-l-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylthio-lH-pyrazole-3-carboxaldehyde oxime:
    5-Amino-1 -[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfïnyl-1H-pyrazole-3-carboxaldehyde oxime;
    5-Amino-1 -[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime;
    5-Amino-1-[2.6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfmyl-lH-pyrazole-3-carboxaldehyde oxime; l-[2.6-Dichloro-4-(trifluoromethyl)phenyl]-5-ethylamino-4-methylsuIfinyl-1 H-pyrazole-3-carboxaldehyde oxime: l-[2.6-Dichloro-4-(trifluoromethyl)phenyl]-5-methylamino-4-methylsulfinyl-1 H-pyrazole-3-carboxaldehyde oxime;
  6. 6. A process for preparing a compound of formula (I) as defined in Claim 1 which comprises: ι z ~8h~ (a) when R2. R3. R4. R5. Μ. X. Y and Z are defined in Claim 1 and Rjrepresents amino, reacting a compound of formula (II):
    with a compound of formula (III): NH2OY (ΠΙ) wherein Y is defined in Claim 1 ; (b) when R2. R3, R4, R5, Μ. X, Y and Z are as defined in Claim land Rjrepresents amino, reacting a compound of formula (IV):
    (IV) wherein R represents alkyl, with a compound of formula (III) in which R is alkyl andY is defined in Claim 1; (c) when R2, R3, R4, R5, Μ, X, Y and Z are as defined in Claim 1 and Rjrepresents alkylamino or dialkylamino, reacting the corresponding compound offormula (I) wherein Rj represents amino with an alkvlating agent preferably offormula R-hal where R represents alkyl and hal is Cl, Br or I; (d) when R2, R3, R4, R5, Μ, X, Y and Z are as defined in Claim 1 and Rjrepresents hydrogen or alkyl, reacting a compound of formula (V): Γ. U -tfr-
    in which Rj represents hydrogen or alkyl with a compound of formula (III) in whichY is defined above; (e) when R2, R3, R4, R5, Μ, X and Z are as defined in Claim 1. R] representshydrogen or alkyl. and Y is defined as in Claim 1 with the exclusion of hydrogen.formyl. aryl, pyridinyl and pyrimidinyl, reacting the corresponding compound offormula (I) wherein Y represents hydrogen with an appropriate alkvlating or acylatingreagent or Michael acceptor. (f) when Z is RjoNH-or R^R^N-in which Rjg, Rj3 and R14 are alkyl or C-3 to C-6 alkenyl optionally substituted by R] 3, including the cyclic amino compoundsof formula (I), alkylating a compound of formula (I) in which Z represents amino: orby forming the imino ether followed by reducing the imino ether; or by Michaeladdition; (g) when m is 1 or 2 , oxidizing the corresponding compound of formula (I) inwhich m is 0 or 1.
  7. 7. A compound of formula (I bis):
    wherein: A is -NR26‘; Y] is hvdrogen. substituted or unsubstituted alkyl. substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted arvl. -S(O)aR?8, -P(O)R29R30' -P(S)R29r30’ "si(R31 )(R32)(R33^· -C(O)R?7, -C(S)R27, cyano or nitro; Rj9 is hydrogen, alkyl. haloalkyl. or -NR34R35; R20 is -S(O)bR36 or R37; R21 is hvdrogen, halogen. -C(O)R3g, -S(O)CR39, alkyl, haloalkyl, -OR4Q. - N=C(R41XR42), alkenyl, -NR43R44, lH-pyrrol-l-yl, lH-pyrazol-l-yl, or -CH=NOH; r22 · r23 and r25 are independently selected from hydrogen, halogen or alkyl; R24 is halogen, haloalkyl, haloalkoxy, -S(O)(jR45 or SF5; R26 is hydrogen or substituted or unsubstituted alkyl; R27 is hydrogen, substituted or unsubstituted alkyl of Cj to C20? substituted orunsubstituted aryl, -OR45 . -NR47R4g, or -SR49; R28 is substituted or unsubstituted alkyl or substituted or unsubstituted aryl; R29 and R30 are independently selected from alkoxy and thioalkoxy;r31· r32 and r33 are independentlv selected from alkyl, haloalkyl and aryl; R34 and R35 are independently selected from hydrogen or substituted or unsubstituted alkyl; R35 is alkyl, alkenyl, alkynyl, or C3-C6 cycloalkyl each of which is optionallysubstituted by one or more halogens; R37 is alkyl or haloalkyl; R38 is hydrogen, alkyl, haloalkyl. alkoxy or thioalkoxy; R39 is alkyl haloalkyl or aryl; R40 and R41 are independently selected from hydrogen, alkyl and haloalkyl; R42 is alkyl. haloalkyl. alkoxy or phenyl each of which is optionally substituted by one or more groups selected from hydroxy, halogen. alkoxy, -CN, alkyl,-S(O)ealkyl; R43 and R44 are independently selected from hydrogen, Nbb, -S(0)fR5o, -C(O)R51. substituted or unsubstituted alkyl, substituted or unsubstitutedalkenyl and alkynyl; or R43 and R44 form together a divalent alkylene radicalwhich may be interrupted by one or more heteroatoms, preferably selectedfrom oxygen. nitrogen and sulfur; R45 is haloalkyl; -<9>' R.46 and R49 are independently selected from substituted or unsubstituted alkyl andsubstituted or unsubstituted aryl; R47 and R48 are independently selected from hydrogen. substituted or unsubstitutedalkyl and substituted or unsubstituted arvl; or R47 and R48 may form togethera divalent alkylene radical which may be interrupted by one or moreheteroatoms; R5Q is substituted or unsubstituted alkyl; R 5 j is hydrogen, alkyl, haloalkyl, aryl, alkenyl, -OR52, -SR53, or -NR54R55; R52 and R53 are independently selected from alkyl and haloalkyl; R54 and R55 are independently selected from hydrogen, alkyl, haloalkyl and aryl;a, b. c. d. e and f independently represent zéro, one or two; Mi is C-halo, C-CH3, C-CH2F, C-ŒbCl, C-NO2, or N;or a pesticidally acceptable sait thereof.
  8. 8. A compound according to Claim 7 wherein the compound of formula (I bis) has one or more of the following features: A is -NR26-; Y1 is hydrogen, alkyl, or -C(O)R27; Rj9 is hydrogen or NH2; R2o is -S(O)bR36; R21 is -NR43R44; R22 is halogen; R23 and R25 are hydrogen; R24 is haloalkyl; R27 is alkyl or O-alkyl; or M is C-halo.
  9. 9. A compound according to Claims 1,2, 3, 7 or 8 wherein the compoundof formula (I) or (I bis) is:
  10. 10. A compound according to Claim 7 or Claim 8 wherein the compound15 of formula (I bis) is:
  11. 11. A pesticidal composition comprising: (a) a compound of formula (I bis)
    N R ^21 19 R04 (I bis) wherein: A is -NR.26"’' Y j is hydrogen. substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl. substituted or unsubstituted aryl. -S(O)aR.28> -p(O)R29R30> -P(s)r29r3O ~si(R31 Xr32Xr3j)· -C(O)R27, -C(S)R?7. cyano or nitro; R19 is hvdrogen. alkyl, haloalkyl. or -NR34R35; R20 is -S(O)bR36 or R37; R21 is hydrogen, halogen, -C(O)R3g, -S(O)CR39, alkyl, haloalkyl, -OR4Q, - N=C(R4|)(R42), alkenyl, -NR43R44, lH-pyrrol-l-yl. lH-pyrazol-l-yl, or-CH=NOH; R22 > r23 and r25 are independently selected from hydrogen. halogen or alkyl; R24 is halogen, haloalkyl, haloalkoxy, -S(O)cjR45 or SF5; R?6 is hydrogen or substituted or unsubstituted alkyl; R27 is hydrogen, substituted or unsubstituted alkyl of Cj to C20- substituted orunsubstituted aryl, -OR46 . -NR47R4g, or -SR49; R28 is substituted or unsubstituted alkyl or substituted or unsubstituted aryl; R?9 and R3Q are independently selected from alkoxy and thioalkoxy; R3I, R32 and R33 are independently selected from alkyl. haloalkyl and aryl; R34 and R35 are independently selected from hydrogen or substituted or unsubstituted alkyl; R36 is alkyl. alkenyl. alkynyl. or C3-C6 cycloalkyl each of which is optionallysubstituted by one or more halogens; R37 is alkyl or haloalkyl; R38 is hydrogen, alkyl, haloalkyl, alkoxy or thioalkoxy; R39 is alkyl haloalkyl or aryl; R40 and R41 are independently selected from hydrogen, alkyl and haloalkyl; R42 is alkyl, haloalkyl, alkoxy or phenyl each of which is optionally substituted by one or more groups selected from hydroxy, halogen, alkoxy, -CN, alkyl,-S(O)ealkyl; R43 and R44 are independently selected from hydrogen, NH2, -S(O)fR5Q, -C(O)R5}, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl and alkynyl; or R43 and R44 form together a divalent alkylene radical which may be interrupted by one or more heteroatoms, preferably selected from oxygen. nitrogen and sulfur; R45 is haloalkyl; R.46 and R49 are independently selected from substituted or unsubstituted alkyl andsubstituted or unsubstituted aryl; R47 and R48 are independently selected from hydrogen. substituted or unsubstitutedalkyl and substituted or unsubstituted aryl; or R47 and R48 may form together 5 a divalent alkylene radical which may be interrupted by one or more heteroatoms; R5O is substituted or unsubstituted alkyl; R5I is hydrogen, alkyl, haloalkyl. aryl, alkenyl, -OR52, -SR53, or -NR54R55; R52 and R53 are independently selected from alkyl and haloalkyl; 10 R54 and R55 are independently selected from hydrogen, alkyl, haloalkyl and aryl; a, b, c, d, e and f independently represent zéro, one or two; M] is C-halo, C-CH3, C-CH2F, C-CH2CI, C-NO2, or N;or a pesticidally acceptable sait thereof; and (b) an agriculturally acceptable carrier therefor. 15
  12. 12. A method for the control of pests at a locus comprising applying tosaid locus a pesticidally effective amount of a compound of formula (I bis):
    (I bis) 20 wherein: A is -NR26S Y1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryi. -S(O)aR28, -P(O)R29R30, -P(S)R29r30> -Si(R3lXR32)(R33)> 25 -C(O)R27, -C(S)R27, cyano or nitro; Rl 9 is hydrogen, alkyl, haloalkyl, or -NR34R35; r20 îs -S(O)bR36 or R37; R-21 >s hydrogen. halogen. -CfOlRjg. -S(O)CR.39. alkvl. haloalkyl. -OR4Q. - N=C(R4i)(R42). alkenyl. -NR43R44. ΙΗ-pyrrol-l-yL 1 H-pyrazol-1-yl. or - CH=NOH; R22 · R?3 and R25 are independently selected from hydrogen. halogen or alkyl: R74 is halogen, haloalkyl, haloalkoxy, -S(O)(}R45 or SF5; R26 is hydrogen or substituted or unsubstituted alkyl; R27 is hydrogen, substituted or unsubstituted alkyl of Cj to C20, substituted orunsubstituted aryl, -OR46 , -NR47R48, or -3R49; R28 is substituted or unsubstituted alkyl or substituted or unsubstituted aryl; R29 and R3Q are independently selected from alkoxy and thioalkoxy; R3}, R30 and R33 are independently selected from alkyl, haloalkyl and aryl; R34 and R35 are independently selected from hydrogen or substituted or unsubstituted alkyl; R36 is alkyl, alkenyl, alkynyl, or C3-C5 cycloalkyl each of which is optionallvsubstituted by one or more halogens; R37 is alkyl or haloalkyl; R33 is hydrogen, alkyl, haloalkyl, alkoxy or thioalkoxy; R39 is alkyl haloalkyl or aryl; R40 and R41 are independently selected from hydrogen, alkyl and haloalkyl; R42 is alkyl, haloalkyl, alkoxy or phenyl each of which is optionallv substituted by one or more groups selected from hydroxy/fiàlogen. alkoxy, -CN, alkyl,-S(O)ealkyl; R43 and R44 are independently selected from hydrogen, NH2, -S(O)fR5Q, -C(O)R5i, substituted or unsubstituted alkyl, substituted or unsubstitutedalkenyl and alkynyl; or R43 and R44 form together a divalent alkylene radicalwhich may be interrupted by one or more ’neteroatoms, preferably selectedfrom oxygen, nitrogen and sulfur; R45 is haloalkyl; R46 and R49 are independently selected from substituted or unsubstituted alkyl andsubstituted or unsubstituted aryl; R47 and R43 are independently selected from hydrogen, substituted or unsubstitutedalkyl and substituted or unsubstituted aryl; or R47 and R4g may form togethera divalent alkylene radical which may be interrupted by one or moreheteroatoms; R50 is substituted or unsubstituted alkyl; R5I is hydrogen, alkyl, haloalkyl, aryl, alkenyl, -OR52. -SR53, or -NR54R55; R52 and R53 are independently selected from alkyl and haloalkyl; 'Ί'- 01Ί2>9 R.54 a°d r55 are independentlv selected from hydrogen, alkyl. haloalkyi and aryla. b. c, d, e and f independentlv represent zéro, one or two; Mi is C-halo, C-CH3. C-CH2F. C-CH?C1. C-NO2, or N;or a pesticidally acceptable sait thereof.
OA9900143A 1996-12-24 1999-06-24 Pesticidal 1-arylpyrazoles OA11299A (en)

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AU745770B2 (en) 2002-03-28
ID19261A (id) 1998-06-28
EG21703A (en) 2002-02-27
CN1214010C (zh) 2005-08-10
JP2001507002A (ja) 2001-05-29
PL197799B1 (pl) 2008-04-30
BG103591A (en) 2000-11-30
MY118892A (en) 2005-02-28
PA8443401A1 (es) 2000-05-24
IL154005A0 (en) 2003-07-31
EP0948485B1 (fr) 2002-09-25
TW476757B (en) 2002-02-21
NZ336419A (en) 2001-03-30
WO1998028278A1 (fr) 1998-07-02
EA199900599A1 (ru) 2000-02-28
SK85999A3 (en) 2000-05-16
DE69715911T2 (de) 2003-05-28
AP1039A (en) 2002-01-23
ATE224877T1 (de) 2002-10-15
KR20000062320A (ko) 2000-10-25
AR028315A2 (es) 2003-05-07
DE69715911D1 (de) 2002-10-31
HUP0000482A2 (hu) 2000-06-28
CN1094928C (zh) 2002-11-27
HUP0000482A3 (en) 2001-08-28
DK0948485T3 (da) 2003-02-03
EE04306B1 (et) 2004-06-15
CO5050290A1 (es) 2001-06-27
CZ294765B6 (cs) 2005-03-16
AP9901589A0 (en) 1999-06-30
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HRP970704B1 (en) 2006-11-30
AR009154A1 (es) 2000-03-08
UA72183C2 (uk) 2005-02-15
EA003186B1 (ru) 2003-02-27
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US6350771B1 (en) 2002-02-26
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MA24431A1 (fr) 1998-07-01
BR9714187B1 (pt) 2010-05-18
EP0948485A1 (fr) 1999-10-13
HRP970704A2 (en) 1998-10-31
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SK283823B6 (sk) 2004-02-03
ES2179386T3 (es) 2003-01-16
PL334282A1 (en) 2000-02-14
CA2275920A1 (fr) 1998-07-02
IL130601A (en) 2004-07-25
IL130601A0 (en) 2000-06-01
CR5676A (es) 1998-09-28
AU5759998A (en) 1998-07-17
CZ228399A3 (cs) 1999-11-17
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