WO1995000491A1 - Sulfonates arthropodicides - Google Patents

Sulfonates arthropodicides Download PDF

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Publication number
WO1995000491A1
WO1995000491A1 PCT/US1994/006346 US9406346W WO9500491A1 WO 1995000491 A1 WO1995000491 A1 WO 1995000491A1 US 9406346 W US9406346 W US 9406346W WO 9500491 A1 WO9500491 A1 WO 9500491A1
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group
alkyl
haloalkyl
optionally substituted
independently selected
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PCT/US1994/006346
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English (en)
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Bruce Lawrence Finkelstein
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Dunlena Pty Ltd.
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Priority to AU71003/94A priority Critical patent/AU7100394A/en
Publication of WO1995000491A1 publication Critical patent/WO1995000491A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/64—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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • 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
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms 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
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms

Definitions

  • U.S. Patents 4,791,127, U.S. 4,987,141, U.S. 3,818,102 and U.S. 3,966,754 disclose insecticidal sulfonates.
  • the instant invention is distinguished from these patents in the unique character of the R 1 and R 2 substitution.
  • This invention pertains to compounds of Formula I, including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use to control arthropods in both agronomic and nonagronomic environments.
  • the compounds are:
  • R 1 is selected from the group CN, NO 2 , OR 7 , C(O)R 7 , C(O)OR 7 , C(O)N(R 7 )R 8 ,
  • R 2 is selected from the group H, C 1 -C 3 alkyl, CN, C(O)OR 7 and C(O)N(R 7 )R 8 ;
  • R 3 and R 4 are independently selected from the group C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C ! -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl,
  • C 3 -C 6 halocycloalkylsulfonyl C 5 -C 6 cycloalkenyl, C 5 -C 6 halocycloalkenyl, C 5 -C 6 cycloalkenyloxy, C 5 -C 6 halocycloalkenyloxy, C 5 -C 6 cycloalkenylthio, C 5 -C 6 halocycloalkenylthio, C 5 -C 6 cycloalkenylsulfinyl,
  • C 5 -C 6 halocycloalkenylsulfonyl each optionally substituted with a substituent selected from the group R 9 ; H; CN; NO 2 ; halogen; C 2 -C 6 alkylcarbonyl; C 2 -C 6 haloalkylcarbonyl; C 2 -C 6 alkoxycarbonyl; C 2 -C 6 haloalkoxycarbonyl; C(O)N(R 10 )R 11 ; C(S)N(R 10 )R 1 1 ; S(O) 2 N(R 10 )R 11 ; C(O)H; N(R 10 )R 11 ; phenyl optionally substituted with 1 or 2 substituents independently selected from the group W; benzyl optionally substituted with 1 or 2 substitutents independently selected from the group W;
  • R 5 is selected from the group C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl each optionally substituted with a substituent selected from the group R 9 ; C 1 -C 6 haloalkyl; C 3 -C 6 halocycloalkyl; C 2 -C 6 haloalkenyl;
  • R 6 is selected from the group halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 3 -C 6
  • halocycloalkyl C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 4 -C 7 cycloalkylalkyl,
  • R 7 and R 8 are independently selected the group C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, phenyl optionally substituted with 1 or 2 substituents independently selected from the group W and benzyl optionally substituted with 1 or 2 substitutents independently selected from the group W;
  • R 9 is selected from the group CN, SCN, NO 2 , OH, OR 12 , SR 12 , S(O)R 12 ,
  • R 10 is selected from the group C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 5 alkoxy, C 2 -C 5 alkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl and C 4 -C 7 cycloalkylalkyl each optionally substituted with a substituent selected from the group R 9 ; N(R 10 )R 11 ; pheny
  • R 11 is selected from the group H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)H,
  • R 10 and R 11 are taken together to form a member selected from the group
  • R 12 is selected from the group H, C 1 -C 3 alkyl and C 1 -C 3 haloalkyl;
  • R 13 and R 14 are independently selected from the group C 1 -C 3 alkyl and C 1 -C 3 haloalkyl;
  • G is selected from the group C(O), C(S), S, S(O) and S(O) 2 ;
  • W is selected from the group halogen, NO 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkylthio, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 4 alkylcarbonyl and C 2 -C 4 alkoxycarbonyl;
  • n 0, 1, 2, 3, 4, 5 or 6;
  • n 0 or 1.
  • Preferred Compounds A are compounds wherein: R 1 is selected from the group CN and C(O)OR 7 ;
  • R 2 is H
  • R 3 and R 4 are independently selected from the group H, halogen, CN, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy and C 1 -C 2 alkylthio;
  • R 5 is selected from the group C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6
  • R 9 is selected from the group CN and OR 12 ;
  • G is selected from the group C(O), S, S(O) and S(O) 2 .
  • Preferred Compounds B are Compounds A wherein Q is Q-2. Preferred
  • Compounds C are Compounds A wherein Q is Q-7.
  • Preferred Compounds D are
  • Preferred Compounds E are Compounds A wherein Q is Q-10.
  • Preferred Compounds F are Compounds A wherein Q is Q-11.
  • Specifically preferred for biological activity is Compound G of Preferred C which is:
  • methyl [[[1-(propylsulfonyl)-1H-pyrazol-3-yl]oxy]sulfonyl]acetate Compounds of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers and geometric isomers.
  • one stereoisomer may be more active than the others and how to separate said stereoisomers.
  • the present invention comprises racemic mixtures, individual stereoisomers, and optically active mixtures of compounds of Formula I as well as agriculturally suitable salts thereof.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” denotes straight-chain or branched alkyl such as methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers.
  • Alkenyl denotes straight-chain or branched alkenes such as 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.
  • Alkenyl also denotes polyenes such as 1,3-butadiene and 1,3,5-hexatriene.
  • Alkynyl denotes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 3-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also denote moieties comprised of multiple triple bonds such as 2,4-hexadiyne.
  • Alkoxy denotes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • alkynyloxy denotes straight-chain or branched alkynyloxy moieties. Examples include HC ⁇ CCH 2 O, CH 3 C ⁇ CCH 2 O and CH 3 C ⁇ CCH 2 CH 2 O.
  • Alkylthio denotes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylsulfinyl denotes both enantiomers of an alkylsulfinyl group. For example, CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsufinyl isomers. Examples of
  • alkylsulfonyl include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
  • Haloalkylthio alkylthio, alkylsulfinyl and alkylsulfonyl substituted by halogen.
  • Cycloalkyl denotes, for example,
  • cyclopropyl cyclobutyl, cyclopentyl, and cyclohexyl.
  • cycloalkylthio denotes the same groups linked through an sulfur atom such as cyclopentylthio and
  • cyclohexylthio denotes the cycloalkylthio substituted by halogen.
  • Cycloalkenyl denotes groups such as cyclopentenyl and cyclohexenyl.
  • cycloalkylalkyl includes cyclopropylmethyl, cyclohexylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups.
  • alkylcarbonyl denotes carbonyl attached to an alkyl group examples include CH 3 C(O), CH 3 CH 2 C(O) and the different propyl, butyl, pentyl and hexyl isomers.
  • alkoxycarbonyl denotes carbonyl attached to an alkoxy group examples include CH 3 OC(O),
  • halogen either alone or in compound words such as “haloalkyl”, denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, ClCH 2 , CF 3 CH 2 and CF 3 CCl 2 .
  • haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CCl 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, CF 2 HCH 2 CH 2 O and CF 3 CH 2 O.
  • haloalkylthio examples include CCl 3 S, CF 3 S, CCl 3 CH 2 S and CH 2 ClCH 2 CH 2 S.
  • haloalkylsulfonyl examples include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2 and CF 3 CF 2 S(O) 2 .
  • the total number of carbon atoms in a substituent group is indicated by the "C i -C j " prefix where i and j are numbers from 1 to 7.
  • C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl.
  • Compounds of Formula I can be prepared by reaction of the corresponding hydroxy compound (1) with the appropriate sulfonyl halide (2) and a base such as triethylamine or pyridine in a solvent such as dichloromethane or tetrahydrofuran as shown in Equation 1.
  • a base such as triethylamine or pyridine
  • a solvent such as dichloromethane or tetrahydrofuran
  • Sulfonyl halides 2 can be prepared by the reaction of an alkyl halide (3) with sodium sulfite followed by reaction with a halogenating agent such as phosphorous oxychloride and/or phosphorous pentachloride as shown in Equation 2.
  • Sulfonyl halides can be also be prepared by other methods known to one skilled in the art (see Hoyle, J., In the Chemistry of Sulphonic Acids, Esters and their Derivatives; Patai, S. and
  • Compounds 1 can exist as the carbonyl tautomer depending on the nature of the Q group.
  • the synthesis of hydroxy Compounds 1 wherein Q is Q-1, Q-2, Q-3, Q-4, Q-8, Q-9 or Q-10 is described in the art.
  • hydroxypyrazoles A general review for the synthesis of hydroxypyrazoles can be found in Wiley, et al., The Chemistry of Heterocyclic Compounds, Pyrazolones, Pyrazolidones and Derivatives:, Vol. 20, Wiley, New York, (1964). More specifically, the hydroxy Compounds 1 wherein Q is Q-5 can be prepared from the appropriate ⁇ -dicarbonyl compound or a synthetic equivalent such as acetylenic ester or ⁇ -oxodithioketene acetal and the appropriate Compound 4 in the presence of base as shown in Equation 3. The synthesis of Compounds 4 is known.
  • the compounds of Formula 5 can be prepared by treatment of an alkoxypyrazole 6 with the appropriate reagent (7) and base as shown in Equation 5.
  • the synthesis of 4-alkoxypyrazoles is known to one skilled in the art see, for example, Pluempe, H. and Schegk, E., Arch. Pharm., 300, 704, (1967).
  • compounds of Formula I wherein Q is Q-5 or Q-7 can be prepared by reaction of a pyrazole sulfonate 8 with a compound of Formula 7 and base as shown in Equation 6.
  • the ratio of products obtained will depend on the nature of the R 3 and R 4 groups. In some instances, only one product will be obtained.
  • the compounds of Formula 8 can be prepared by the reaction of a
  • Equation 7 hydroxypyrazole 9 with a sulfonyl halide and base as shown in Equation 7.
  • the synthesis of compounds of Formula 9 is known. Equation 7
  • compounds of Formula I wherein Q is Q-6 can be prepared from pyrazole sulfonates of Formula 10 which in turn can be prepared from hydroxy pyrazoles of Formula 11 as shown in Equation 8.
  • Equation 9 The hydroxy Compounds 1 wherein Q is Q-11 (which will exist predominantly as the carbonyl tautomer) can be prepared by treatment of the NH heterocycle 12 with the appropriate reagent 7 as shown in Equation 9. Equation 9
  • the synthesis of compounds of Formula 14 is known to one skilled in the art.
  • Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent.
  • Useful formulations include dusts, granules, baits, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent.
  • Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill.
  • Water-dispersible granules can be produced by agglomerating a fine powder
  • composition see for example, Cross et al., Pesticide Formulations, Washington, D.C., 1988, pp 251-259.
  • Suspensions are prepared by wet-milling; see, for example,
  • Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-148, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546.
  • the compounds of this invention exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding, stem or root feeding, seed-feeding, aquatic and
  • arthropods includes insects, mites and nematodes which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health. Those skilled in the art will appreciate that not all compounds are equally effective against all growth stages of all pests.
  • all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the Order Lepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order Coleoptera; eggs, immatures and adults of the Orders Hemiptera and Homoptera; eggs, larvae, nymphs and adults of the Order Acari; eggs, immatures and adults of the Orders Thysanoptera, Orthoptera and
  • the compounds of this invention are also active against pests of the Orders Hymenoptera, Isoptera, Siphonaptera, Blattaria, Thysanura and Psocoptera; pests belonging to the Class Arachnida and Phylum Platyhelminthes.
  • the compounds are active against southern corn rootworm (Diabrotica undecimpunctata howardi), aster leafhopper (Mascrosteles fascifrons), boll weevil (Anthonomus grandis), two-spotted spider mite (Tetranychus urticae), fall a ⁇ nyworm (Spodoptera frugiperda), black bean aphid (Aphis fabae), green peach aphid (Myzus persica), cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis noxia), English grain aphid (Sitobion avenae), tobacco budworm (Heliothis virescens), rice water weevil (Lissorhoptrus oryzophilus), rice leaf beetle (Oulema oryzae), whitebacked planthopper (Sogatella furcifera), green leafhopper (Nephotettix cincticeps),
  • Tetranychidae including Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus, Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi, Panonychus citri, Eotetranychus carpini borealis, Eotetranychus, hicoriae, Eotetranychus sexmaculatus, Eotetranychus yumensis, Eotetranychus banksi and Oligonychus pratensis;
  • Tenuipalpidae including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpus obovatus; Eriophyidae including Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae. See WO 90/10623 and WO 92/00673 for more detailed pest descriptions.
  • insecticides fungicides, nematocides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellants, attiractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • insecticides such as avermectin B, monocrotophos, carbofuran, tetrachlorvinphos, malathion, parathion-methyl, methomyl, chlordimeform, diazinon, deltamethrin, oxamyl, fenvalerate, esfenvalerate, permethrin, profenofos, sulprofos, triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb, acephate, azinphosmethyl, chlorpyrifos, dimethoate, fipronil, flufenprox, fonophos, isofenphos, methidathion, metha-midophos, phosmet,
  • fungicides such as carbendazim, thiuram, dodine, maneb, chloroneb, benomyl, cymoxanil, fenpropidine, fenpropimo ⁇ h, triadimefon, captan, thiophanate-methyl, thiabendazole, phosethyl-Al, chlorothalonil, dichloran, metalaxyl, captafol, iprodione, oxadixyl, vinclozolin, kas
  • nematocides such as aldoxycarb, fenamiphos and fosthietan; bactericides such as oxytetracyline, streptomycin and tribasic copper sulfate; acaricides such as binapaciyl, oxythioquinox, chlorobenzilate, dicofol, dienochlor, cyhexatin, hexythiazox, amitraz, propargite, tebufenpyrad and fenbutatin oxide; and biological agents such as
  • Arthropod pests are controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying one or more of the compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.
  • the present invention further comprises a method for the control of foliar and soil inhabiting arthropods and nematode pests and protection of agronomic and/or nonagronomic crops, comprising applying one or more of the compounds of Formula I, or compositions containing at least one such compound, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.
  • a preferred method of application is by spraying.
  • granular formulations of these compounds can be applied to the plant foliage or the soil.
  • the compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use.
  • a preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, and synergists and other solvents such as piperonyl butoxide often enhance compound efficacy.
  • the rate of application required for effective control will depend on such factors as the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.001 kg/hectare may be sufficient or as much as 8 kg hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required.
  • Control efficacy represents in3ibition of arthropod development (including mortality) that causes significantly reduced feeding.
  • the pest control protection afforded by the compounds is not limited, however, to these species. See Index Tables A-E for compound descriptions.
  • Test units each consisting of an 8 ounce (230 mL) plastic cup containing a one- inch square (2.54 cm 2 ) of a wheatgerm diet, were prepared. Solutions of each of the test compound in 75/25 acetone/distilled water solvent were sprayed into the tray and cup. Spraying was accomplished by passing the tray and cup, on a conveyer belt, directly beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.5 pounds of active ingredient per acre (about 0.55 kg/ha) at 30 p.s.i. (207 kPa). After the spray on the cups had dried, five second-instar larvae of the southern corn rootworm (Diabrotica undecimpunctata howardi) were placed into each cup.
  • Test units were prepared from a series of 12 ounce (350 mL) cups, each containing oat (Avena sativa) seedlings in a 1 inch (2.54 cm) layer of sterilized soil.
  • the test units were sprayed as described in TEST A with individual solutions of the test compounds. After the oats had dried from the spraying, between 10 and 15 adult aster leafhoppers (Mascrosteles fascifrons) were aspirated into each of the cups.
  • the cups were covered with vented lids and held at 27°C and 50% relative humidity for 48 hours, after which time mortality readings were taken. Of the compounds tested, 80% or greater control was achieved using the following compounds: 1, 4, 14*, 15 and 16.
  • kidney bean leaves that had been infested on the undersides with 25 to 30 adult mites (Tetranychus urticae) were sprayed with their undersides facing up on a hydraulic sprayer with a solution of the test compounds in 75/25 acetone/distilled water solvent. Spraying was accomplished by passing the leaves, on a conveyor belt, directly beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.55 pounds of active ingredient per acre (about 0.5 kg/ha) at

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

L'invention concerne des composés arthropodicides et nématocides, des compositions contenant ces composés, ainsi que l'utilisation des composés de formule (I) dans laquelle Q, R1 et R2 sont tels que définis dans la description.
PCT/US1994/006346 1993-06-17 1994-06-10 Sulfonates arthropodicides WO1995000491A1 (fr)

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AU71003/94A AU7100394A (en) 1993-06-17 1994-06-10 Arthropodicidal sulfonates

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US7853093A 1993-06-17 1993-06-17
US08/078,530 1993-06-17

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WO1995000491A1 true WO1995000491A1 (fr) 1995-01-05

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7067539B2 (en) 2001-02-08 2006-06-27 Schering Corporation Cannabinoid receptor ligands
US7507767B2 (en) 2001-02-08 2009-03-24 Schering Corporation Cannabinoid receptor ligands

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2233324A1 (fr) * 1973-06-14 1975-01-10 Ciba Geigy Ag
EP0220857A1 (fr) * 1985-10-07 1987-05-06 Nippon Kayaku Kabushiki Kaisha Dérivés d'alcanesulfonates et leur application comme insecticides, acaricides ou nématocides
WO1993010096A1 (fr) * 1991-11-19 1993-05-27 Dunlena Pty. Ltd. Sulfonates arthropodicides et nematocides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2233324A1 (fr) * 1973-06-14 1975-01-10 Ciba Geigy Ag
EP0220857A1 (fr) * 1985-10-07 1987-05-06 Nippon Kayaku Kabushiki Kaisha Dérivés d'alcanesulfonates et leur application comme insecticides, acaricides ou nématocides
WO1993010096A1 (fr) * 1991-11-19 1993-05-27 Dunlena Pty. Ltd. Sulfonates arthropodicides et nematocides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7067539B2 (en) 2001-02-08 2006-06-27 Schering Corporation Cannabinoid receptor ligands
US7507767B2 (en) 2001-02-08 2009-03-24 Schering Corporation Cannabinoid receptor ligands
US7718702B2 (en) 2001-02-08 2010-05-18 Schering Corporation Cannabinoid receptor ligands

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