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WO1997003976A1 - Derives de semicarbazone et pesticides - Google Patents

Derives de semicarbazone et pesticides Download PDF

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Publication number
WO1997003976A1
WO1997003976A1 PCT/JP1996/002022 JP9602022W WO9703976A1 WO 1997003976 A1 WO1997003976 A1 WO 1997003976A1 JP 9602022 W JP9602022 W JP 9602022W WO 9703976 A1 WO9703976 A1 WO 9703976A1
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Prior art keywords
group
substituted
alkyl
hydrogen atom
och
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PCT/JP1996/002022
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English (en)
Inventor
Kazuo Yagi
Tadashi Ohtsu
Atsushi Irimata
Tomoyuki Ogura
Takeshi Mita
Toshiro Miyake
Youichi Inoue
Norihiko Mimori
Shinji Takii
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Nissan Chemical Industries, Ltd.
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Application filed by Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to AU64703/96A priority Critical patent/AU6470396A/en
Publication of WO1997003976A1 publication Critical patent/WO1997003976A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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    • 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
    • C07D213/86—Hydrazides; Thio or imino analogues thereof
    • 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
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    • 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
    • C07D231/40—Acylated on said nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • the present invention relates to novel semicarbazone derivatives and pesticides containing such derivatives as active ingredients.
  • the present inventors have conducted extensive researches on semicarbazone derivatives and as a result, have found that novel 5- or 6-membered hetero ring-substituted semicarbazone derivatives and their salts exhibit excellent pesticidal activities, particularly insecticidal activities at a low dose, and they are very useful compounds substantially free from adverse effects against mammals, fishes and beneficial insects.
  • the present invention has been accomplished on the basis of these discoveries.
  • the present invention provides a semicarbazone derivative of the formula (I) or its salt:
  • Q is any one of Q-1 to Q-37:
  • J is any one of J-1 to J-33, provided that when Q is and G is G-1, J is other than J-33;
  • G is any one of G-1 to G-8, provided that when Q is Q-37 and J is J-33, G is other than G-1;
  • W is an oxygen atom or a sulfur atom
  • each of X, Y and Z which are independent of one another, is a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 1-6 haloalkyl group, a C 2-6 haloalkenyl group, a C 2-6
  • haloalkynyl group a C 3-6 cycloalkyl group, a C 3-6
  • halocycloalkyl group a C 4-7 cycloalkylalkyl group, -OR 10 , -CN, -N 3 , -SCN, -NO 2 , -SH, -S(O) r R 7 , -OCHO, -CHO, -C(O)R 7 , -C(O)OR 7 , -C(O)NR 7 R 8 , -S(O) 2 NR 7 R 8 , -NR 7 R 8 , -NR 8 CHO,
  • each of R 1 , R 2 and R 3 which are independent of one another, is a hydrogen atom, a C 1-6 alkyl group, a
  • -N CR 11 R 12 , -P(O)(OR 13 ) 2 , -P(S)(OR 13 ) 2 , -S(O) r R 7 ,
  • each of R 4 and R 5 which are independent of each other, is a hydrogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 1-6 haloalkyl group, a C 2-6 haloalkenyl group, a C 2-6 haloalkynyl group, a C 3-6 cycloalkyl group, a C 3-6 halocycloalkyl group, a C 4-7 cycloalkylalkyl group, a C 2-6 alkoxyalkyl group, a C 2-6 alkylthioalkyl group, a C 1-6 nitroalkyl group, a C 2-6 cyanoalkyl group, a C 3-8 alkoxycarbonylalkyl group, -CHO, -C(O)R 7 , -C(O)OR 7 , -C(O)NR 7 R 8 , or -S(O) 2
  • R 6 is a hydrogen atom, a halogen atom, a hydroxyl group, -CN, -NO 2 , a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, a C 1- 6 alkylthio group, a C 1-6 haloalkylthio group, a C 1-6 alkylsufonyl group, a C 1-6 haloalkylsulfonyl group, a C 2-6 alkoxycarbonyl group, an amino group, or a di-C 1-6 alkylamino group;
  • R 7 is a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 1-6 haloalkyl group, a C 2-6 haloalkenyl group, a C 2-6 haloalkynyl group, a C 3-6 cycloalkyl group, a C 3-6 halocycloalkyl group, a C 4-7 cycloalkylalkyl group, a C 2-6 alkoxyalkyl group, a C 2-6 alkylthioalkyl group, a C 1-6 nitroalkyl group, a C 2-6 cyanoalkyl group, a C 3-8 alkoxycarbonylalkyl group, a phenyl group which may be substituted by (R 6 ) q , a benzyl group which may be
  • R 8 is a hydrogen atom, a C 1-4 alkyl group, a C 2-4 alkenyl group, or a C 2-4 alkynyl group;
  • R 7 and R 8 may together form -CH 2 CH 2 CH 2 CH 2 -,
  • R 9 is a C 1-3 alkoxy group, a C 1-3 haloalkoxy group, -CN, -NO 2 , -S(O) r R 7 , -P(O)(OR 13 ) 2 , -P(S) (OR 13 ) 2 , -C(O)R 7 , -C(O)OR 7 , or a phenyl group which may be substituted by
  • R 10 is a hydrogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 1-6 haloalkyl group, a C 2-6 haloalkenyl group, a C 2-6 haloalkynyl group.
  • R 11 is a hydrogen atom, a C 1-4 alkyl group, -C(O)R 7 , or -C(O)OR 7 ;
  • R 12 is a hydrogen atom, a C 1-4 alkyl group, a C 1-4 haloalkyl group, or a phenyl group which may be
  • R 11 and R 12 may together form
  • R 13 is a C 1-3 alkyl group, or a phenyl group which may be substituted by (R 6 ) q ;
  • R 14 is a C 1-4 alkyl group
  • R 15 is a C 1-18 alkyl group
  • R 16 and R 17 which are independent of each other is a C 1-4 alkyl group, or R 16 and R 17 may together form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, or -CH 2 CH 2 OCH 2 CH 2 -; each of R 18 and R 19 which are independent of each other, is a C 1-4 alkyl group;
  • R 20 is a C 1-4 alkyl group, or a phenyl group which may be substituted by (R 6 ) q ;
  • k is an integer of from 0 to 5, provided that when k is from 2 to 5, the plurality of X may be the same or different;
  • n is an integer of from 0 to 5, provided that when m is from 2 to 5, the plurality of Y may be the same or different;
  • n is an integer of from 0 to 5, provided that when n is from 2 to 5, the plurality of Z may be the same or different;
  • p is an integer of from 1 to 3, provided that when p is 2 or 3, the plurality of R 9 may be the same or
  • q is an integer of from 0 to 4, provided that when q is from 2 or 4, the plurality of R 6 may be the same or different;
  • r is an integer of from 0 to 2.
  • the present invention also provides a pesticide which contains at least one such semicarbazone derivative or its salt as an active ingredient.
  • each substituent disclosed above may be linear, branched or cyclic.
  • n- means normal, i- means iso, sec- means secondary, t- means tertiary, and c- means cyclo.
  • the alkyl group may, for example, be a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a sec-butyl group, a t- butyl group, a n-pentyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a 1-ethylbutyl group, a 2-ethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, or a 1-ethyl-1-butyl group.
  • the alkenyl group may, for example, be an ethenyl group, a 1-propenyl group, a 2-propenyl group, a 2-methyl-2-propenyl group, a 2-butenyl group, a 3-methyl-2-butenyl group, a 3-butenyl group, a 4-pentenyl group, or a 2,3-dimethyl-2-butenyl group.
  • the alkynyl group may, for example, be an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, or a 4,4-dimethylpentynyl group.
  • the cycloalkyl group may, for example, be a c-propyl group, a c-butyl group, a c-pentyl group, a c-hexyl group or a 1-methyl-c-propyl group.
  • the pyridyl group may, for example, be a 2-pyridyl group, a 3-pyridyl group or a 4-pyridyl group.
  • the alkoxy group may, for example, be a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, an i-butoxy group, a sec-butoxy group or a t-butoxy group.
  • the alkylthio group may, for example, be a methylthio group, an ethylthio group, a n-propylthio group, an i-propylthio group, a n-butylthio group, an i-butylthio group, a sec-butylthio group or a t-butylthio group.
  • the halogen atom may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • W is an oxygen atom or a sulfur atom, preferably an oxygen atom.
  • Each of X, Y and Z which are independent of one another, may, for example, be a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, C 1-6 haloalkyl group, a C 2-6 haloalkenyl group, a C 2-6 haloalkynyl group, a C 3-6 cycloalkyl group, a C 3-6 halocycloalkyl group, a C 4-7 cycloalkylalkyl group, a hydroxyl group, a C 1-6 alkoxy group, a C 2-6 alkenyloxy group, a C 2-6 alkynyloxy group, a C 1-6 haloalkoxy group, a C 2-6 haloalkenyloxy group, a C 2-6 haloalkynyloxy group, a C 3-6 cycloalkyloxy group,
  • alkylthioalkyloxy group a C 2-7 cyanoalkyloxy group, a C 3-8 alkoxycarbonylalkyloxy group, a C 2-7 alkylcarbonyloxy group, a C 3-7 alkenylcarbonyloxy group, a C 3-7
  • alkynylcarbonyloxy group a C 2-7 haloalkylcarbonyloxy group, a C 3-7 haloalkenylcarbonyloxy group, a C 3-7
  • alkoxyalkylcarbonyloxy group a C 3-7 alkylthioalkylcarbonyloxy group, a C 3-7
  • alkylthioalkylthio group a C 2-6 cyanoalkylthio group, a C 3-8 alkoxycarbonylalkylthio group, a phenylthio group which may be substituted by (R 6 ) q , a benzylthio group which may be substituted by (R 6 ) q , a pyridylthio group which may be substituted by (R 6 ) q , a C 1-6 alkylsulfinyl group, a C 2-6 alkenylsulfinyl group, a C 2-6
  • alkynylsulfinyl group a C 1-6 haloalkylsulfinyl group, a C 2-6 haloalkenylsulfinyl group, a C 2-6 haloalkynylsulfinyl group, a C 3-6 cycloalkylsulfinyl group, a C 3-6
  • cycloalkylalkylsulfinyl group a C 2-6 alkoxyalkylsulfinyl group, a C 2-6 alkylthioalkylsulfinyl group, a
  • phenylsulfinyl group which may be substituted by (R 6 ) q , a benzylsulfinyl group which may be substituted by (R 6 ) q , a pyridylsulfinyl group which may be substituted by (R 6 ) q , a C 1-6 alkylsulfonyl group, a C 2-6 alk ⁇ nylsulfonyl group, a C 2-6 alkynylsulfonyl group, a C 1-6 haloalkylsulfonyl group, a C 2-6 haloalkenylsulfonyl group, a C 2-6
  • haloalkynylsulfonyl group a C 3-6 cycloalkylsulfonyl group, a C 3-6 halocycloalkylsulfonyl group, a C 4-7 cycloalkylalkylsulfonyl group, a C 2-6 alkoxyalkylsulfonyl group, a C 2-6 alkylthioalkylsulfonyl group, a C 2-6 cyanoalkylsulfonyl group, a C 3-8
  • alkoxycarbonylalkylsulfonyl group a phenylsulfonyl group which may be substituted by (R 6 ) q , a benzylsulfonyl group which may be substituted by (R 6 ) q , a pyridylsulfonyl group which may be substituted by (R 6 ) q , -CHO, a C 2-7 alkylcarbonyl group, a C 3-7 alkenylcarbonyl group, a C 3-7 alkynylcarbonyl group, a C 2-7 haloalkylcarbonyl group, a C 4-7 cycloaklylcarbonyl group, a C 4-7
  • halocycloalkylcarbonyl group a C 3-7 alkoxyalkylcarbonyl group, a C 3-7 alkylthioalkylcarbonyl group, a C 3-7 cyanoalkylcarbonyl group, a benzoyl group which may be substituted by (R 6 ) q , a benzylcarbonyl group which may be substituted by (R 6 ) q , a pyridylcarbonyl group which may be substituted by (R 6 ) q , a C 2-7 alkoxycarbonyl group, a C 2-7 haloalkoxycarbonyl group, a C 4-7
  • pyridyloxycarbonyl group which may be substituted by (R 6 ) q , an N-C 1-6 alkyl-C 2-5 alkylcarbamoyl group, a C 2-7 mono-alkylaminocarbonyl group, an N-C 1-6 haloalkyl-C 2-5 alkylcarbamoyl group, a C 2-7 monohaloalkylaminocarbonyl group, a phenylaminocarbonyl group which may be
  • haloalkylcarbonylamino group an N-C 1-4 alkyl-C 4-7 cycloalkylcarbonylamino group, an N-C 1-4 alkyl-C 4-7 halocycloalkylcarbonylamino group, a phenylcarbonylamino group which may be substituted by (R 6 ) q , a
  • alkylsulfonylamino group an N-C 1-4 alkyl-C 1-6
  • haloalkylsulfonylamino group a C 1-6 alkylsulfonylamino group, a C 1-6 haloalkylsulfonylamino group, a
  • R 6 may, for example, be a hydrogen atom, a halogen atom, a hydroxyl group, -CN, -NO 2 , a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, a C 1-6 alkylthio group, a C 1-6 haloalkylthio group, a C 1-6 alkylsulfonyl group, a C 1-6 haloalkylsulfonyl group, a C 2-6 alkoxycarbonyl group, an amino group, or a di-C 1-6 alkyl-amino group, and q is an integer of from 0 to 4.
  • X may preferably be, for example, a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, a C 1-6 alkylthio group, a C 1-6 haloalkylthio group, a C 1-6 alkylsulfonyl group, or a C 1-6 haloalkylsulfonyl group.
  • k is an integer of from 0 to 5, preferably 0, 1 or 2.
  • the plurality of X may be the same or different.
  • Z may preferably be, for example, a halogen atom, a cyano group, a nitro group, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, a C 1-6 alkylthio group, a C 1-6 haloalkylthio group, a C 1-6 alkylsulfinyl group, a C 1-6 haloalkylsulfinyl group, a C 1-6 alkylsulfonyl group, a C 1-6
  • n is an integer of from 0 to 5, preferably 1 or 2.
  • the plurality of Z may be the same or different.
  • R 1 , R 2 and R 3 which are independent of one another, may, for example, be a hydrogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 1-6 haloalkyl group, a C 2-6 haloalkenyl group, a C 2-6 haloalkynyl group, a C 3-6 cycloalkyl group, a C 3-6 halocycloalkyl group, a C 4-7 cycloalkylalkyl group, -CHO, a C 2-7 alkylcarbonyl group, a C 3-7 alkenylcarbonyl group, a C 3-7 alkylcarbonyl group, a C 2-7 haloalkylcarbonyl group, a C 3-7 haloalkenylcarbonyl group, a C 3-7
  • haloalkynylcarbonyl group a C 4-7 cycloalkylcarbonyl group, a C 4-7 halocycloalkylcarbonyl group, a C 5-8 cycloalkylalkylcarbonyl group, a C 3-7 alkoxyalkylcarbonyl group, a C 3-7 alkylthioalkylcarbonyl group, a C 3-7 cyanoalkylcarbonyl group, a C 4-9
  • alkoxycarbonylalkylcarbonyl group a benzoyl group which may be substituted by (R 6 ) q , a benzylcarbonyl group which may be substituted by (R 6 ) q , a pyridylcarbonyl group which may be substituted by (R 6 ) q , a C 2-7 alkoxycarbonyl group, a C 3-7 alkenyloxycarbonyl group, a C 3-7
  • alkynyloxycarbonyl group a C 2-7 haloalkoxycarbonyl group, a C 3-7 haloalkenyloxycarbonyl group, a C 3-7 haloalkynyloxycarbonyl group, a C 4-7
  • alkoxyalkoxycarbonyl group a C 3-7
  • alkylthioalkoxycarbonyl group a C 3-7
  • pyridyloxycarbonyl group which may be substituted by (R 6 ) q , a C 2-7 alkyl-thiocarbonyl group, a C 2-7 haloalkyl- thiocarbonyl group, a C 2-7 alkylthio-carbonyl group, a C 2-7 haloalkylthio-carbonyl group, a C 2-7 alkylthio- thiocarbonyl group, a C 2-7 haloalkylthio-thiocarbonyl group, a C 3-8 alkoxycarbonylcarbonyl group, a C 3-8 haloalkoxycarbonylcarbonyl group, an amino group, a C 1-6 alkylamino group, an N-C 1-4 alkyl-C 1-6 alkylamino group, a C 2-7 alkylcarbonylamino group, a di-C 2-7 alkylcarbonylamino group, a C 2-7 alkoxycarbonylamino group
  • alkoxycarbonylalkylsulfonyl group an N-C 1-4 alkyl-C 2-19 alkoxycarbonylaminothio group, a di-C 1-4 alkyl-aminothio group, a 1-pyrrolidin ⁇ thio group, a 1-piperidinothio group, a 1-morpholinothio group, a phenyl group which may be substituted by (R 6 ) q , a C 2-9 alkoxyalkyl group, a C 2-9 haloalkoxyalkyl group, a C 2-7 cyanoalkyl group, a C 2-12 alkylthioalkyl group, a C 3-13 alkylcarbonylalkyl group, a C 3-13 alkoxycarbonylalkyl group, or a benzyl group which may be substituted by (R 6 ) q .
  • R 6 may, for example, be a hydrogen atom, a halogen atom, a hydroxyl group, -CN, -NO 2 , a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, a C 1- 6 alkylthio group, a C 1-6 haloalkylthio group, a C 1-6 alkylsulfonyl group, a C 1-6 haloalkylsulfonyl group, a C 2-6 alkoxycarbonyl group, an amino group, or a di-C 1-6 alkyl-amino group, and q is preferably an integer of from 0 to 2.
  • R 1 may, for example, be preferably a hydrogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 1-6 haloalkyl group, a C 2-6 haloalkenyl group, a C 2-6 haloalkynyl group, a C 3-6 cycloalkyl group, a C 3-6 halocycloalkyl group, a C 4-7 cycloalkylalkyl group, a C 2-9 alkoxyalkyl group, a C 2-9 haloalkoxyalkyl group, a C 2-7 cyanoalkyl group, a C 2-12 alkylthioalkyl group, a C 2-12 alkylcarbonylalkyl group, a C 2-12 alkoxycarbonylalkyl group, or a benzyl group which may be substituted by (R 6 ) q .
  • R 6 may, for example, be a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, or a C 1-6 haloalkoxy group, and q is preferably an integer of from 0 to 2.
  • R 2 may, for example, be preferably a hydrogen atom, a C 1-6 alkyl group, a C 2-9 alkoxyalkyl group, or a C 2-7 alkoxycarbonyl group.
  • R 3 may, for example, be preferably a hydrogen atom, a C 1-6 alkyl group, -CHO, a C 2-7 alkylcarbonyl group, a C 3-7 alkenylcarbonyl group, a C 3-7 alkynylcarbonyl group, a C 2-7 haloalkylcarbonyl group, a C 4-7 cycloalkylcarbonyl group, a C 4-7 halocycloalkylcarbonyl group, a C 3-7 alkoxyalkylcarbonyl group, a C 3-7 alkylthioalkylcarbonyl group, a C 3-7 cyanoalkylcarbonyl group, a benzoyl group which may be substituted by (R 6 ) q , a benzylcarbonyl group which may be substituted by (R 6 ) q , a pyridylcarbonyl group which may be substituted by (R 6 ) q , a C 2-7
  • alkoxycarbonyl group a C 2-7 haloalkoxycarbonyl group, a C 4-7 cycloalkyloxycarbonyl group, a C 4-7
  • R 6 may, for example, be a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, or a C 1-6 haloalkoxy group, and q is preferably an integer of from 0 to 2.
  • X is a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-5 alkynyl group, a C 1-6 haloalkyl group, a C 2-6 haloalkenyl group, a C 2-6
  • haloalkynyl group a C 3-6 cycloalkyl group, a C 3-6
  • halocycloalkyl group a C 4-7 cycloalkylalkyl group, -OR 10 , -CN, -NO 2 , -S(O) r R 7 , -OS(O) 2 R 7 , or -C(O)OR 7 ;
  • Y is a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 1-6 haloalkyl group, a C 2-6 haloalkenyl group, a C 2-6
  • haloalkynyl group a C 3-6 cycloalkyl group, a C 3-6
  • R 1 is a hydrogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 1-6 haloalkyl group, a C 2-6 haloalkenyl group, a C 2-6 haloalkynyl group, a C 3-6 cycloalkyl group, a C 3-6 halocycloalkyl group, a C 4 - 7 cycloalkylalkyl group, -CHO, -C(O)R 7 , -C(O)OR 7 ,
  • R 2 is a hydrogen atom, a C 1-6 alkyl group, a C 1-6 alkyl group which may be substituted by (R 9 ) p , or
  • each of R 4 and R 5 which are independent of each other is a hydrogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 3-6 cycloalkyl group, a C 2-6
  • alkoxyalkyl group a C 2-6 alkylthioalkyl group, -C(O)OR 7 , -C(O)NR 7 R 8 , or -S(O) 2 NR 7 R 8 ;
  • R 7 is a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 3-6 cycloalkyl group, or a phenyl group which may be substituted by (R 6 ) q ;
  • R 9 is a C 1-3 alkoxy group, -CN, or -C(O)OR 7 ;
  • R 10 is a hydrogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 3-6 cycloalkyl group, a C 2-7
  • k is an integer of from 0 to 2, provided that when k is 2, two X may be the same or different;
  • n is an integer of from 0 to 3, provided that when m is 2 or 3, the plurality of Y may be the same or
  • n is an integer of from 1 to 3, provided that when n is 2 or 3, the plurality of Z may be the same or
  • Q is Q-1, Q-2, Q-3, Q-4, Q-5, Q-8, Q-9, Q-10, Q-14, Q-15, Q-16, Q-17, Q-18, Q-22, Q-25, Q-27, Q-28, Q-29, Q-30, Q-31, Q-32 or Q-37.
  • J is J-1, J-2, J-7, J-8, J-9, J-10, J-13, J-14, J-15, J-24, J-25, J-26, J-27, J-28, J-30 or J-33.
  • G is G-1.
  • J is J-1, J-2, J-7, J-8, J-9, J-10, J-13, J-14, J-15, J-24, J-25, J-26, J-27, J-28, J-30 or J-33;
  • G is G-1.
  • Q is Q-1 or Q-37;
  • n is an integer of 1 or 2, provided that when m is 2, two Y may be the same or different;
  • n is an integer of 1 or 2, provided that when n is 2, two Z may be the same or different, and the substituted position is the 3-position, the 4-position or the 3- and 4-positions.
  • n is an integer of 1 or 2, provided that when m is 2, two Y may be the same or different, and the substituted position is the 3-position, the 4-position or the 3- and 4-positions;
  • n is an integer of 1 or 2, provided that when n is 2, two Z may be the same or different, and the substituted position is the 3-position, the 4-position or the 3- and 4-positions.
  • W is an oxygen atom
  • X is a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, a C 1-6 alkylthio group, a C 1-6
  • haloalkylthio group a C 1-6 alkylsulfonyl group, or a C 1-6 haloalkylsulfonyl group;
  • Y is a halogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, a C 1-6 alkylthio group, a C 1-6 haloalkylthio group, a C 1-6 alkylsulfonyl group, a C 1-6 haloalkylsulfonyl group, a C 1-6 alkylsulfonyloxy group, a C 1-6
  • Z is a halogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, a C 1-6 alkylthio group, a C 1-6 haloalkylthio group, a C 1-6 alkylsulfinyl group, a C 1-6 haloalkylsulfinyl group, a C 1-6 alkylsulfonyl group, a C 1-6
  • n is an integer of 1 or 2, provided that when m is 2, two Y may be the same or different;
  • n is an integer of 1 or 2, provided that when n is 2, two Z may be the same or different, and the substituted position is the 3-position, the 4-position or the 3- and 4-positions;
  • R 1 is a hydrogen atom, a C 1-6 alkyl group, a C 2-6 alkoxyalkyl group, or a C 2-6 alkylthioalkyl group;
  • R 2 is a hydrogen atom, a C 1-6 alkyl group, a C 2-6 alkoxyalkyl group, or a -C(O)O-C 1-6 alkyl group;
  • R 3 is a hydrogen atom, an amino group, a C 1-6 alkyl group, a -C (O) -C 1-6 alkyl group or a -C (O)O-C 1-6 alkyl group.
  • the compound of the present invention may have E-form and Z-form isomers.
  • the present invention covers such E-form and Z-form as well as a mixture containing such E-form and Z-form in an optional ratio.
  • the compound of the present invention has an asymmetric carbon atom, it includes R-form and S-form.
  • R 1 is a hydrogen atom
  • the compound of the present invention may be in the form of the following tautomers, and such structures are also covered by the present invention.
  • the pesticide means in particular, an agent for controlling insect pests.
  • the compound of the present invention exhibits pesticidal effects against various insect pests at an extremely low dose.
  • the insect pests include, for example, agricultural insect pests such as green rice leafhopper (Nephotettix cincticeps), brown rice
  • sanitary insect pests such as common gnat (Culex pipiens pallens), housefly, German cockroach
  • Formosan subterranean termite Coptotermes formosanus
  • animal pests such as mites, fleas and louses
  • indoor dust mites such as acarid mites (Acaridae), Dermatophaqoides farinae, and Chenyletus malaccensis
  • mollusks such as slugs (Philomycidae) and snails.
  • the compound of the present invention is capable of effectively
  • the compound of the present invention has been found to be an extremely useful compound which is substantially free from adverse effects against mammals, fishes, Crustacea and beneficial insects. On the basis of this discovery, the present invention has been accomplished.
  • the compounds of the present invention are novel semicarbazone
  • each of L 1 , L 2 , L 3 and L 4 is an excellent leaving group such as a chlorine atom, a bromine atom, an iodine atom, an alkylsulfonate group or an arylsulfonate group.
  • a compound of the formula (III) can be obtained by reacting a compound of the formula (II) with e.g.
  • a compound of the formula (I) of the present invention can be obtained by reacting the compound of the formula (V) of the present invention and a compound of the formula (VI) in the presence or absence of a base in an inert solvent.
  • the solvent to be used in Process 1 may, for example, be an aromatic hydrocarbon such as benzene or toluene, or a halogenated hydrocarbon such as carbon tetrachloride or 1,1,2-trichloroethane. It is preferred to employ from 1 to 3 equivalents of phosphorus pentachloride in toluene.
  • the reaction temperature can be set at an optional level within a range of from 0°C to the reflux temperature of the reaction mixture. However, it is preferred to conduct the reaction at a temperature of from 60°C to the reflux temperature.
  • the base to be used in Process 2 may, for example, be an alkali metal alkoxide such as sodium ethoxide or potassium tert-butoxide, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali metal carbonate such as sodium carbonate, potassium carbonate or sodium hydrogen carbonate, an alkali metal hydride such as sodium hydride or potassium hydride, or an organic base such as triethylamine or pyridine.
  • the solvent to be used may be any solvent so long as it does not hinder the reaction.
  • a lower alcohol such as methanol or ethanol
  • an aromatic hydrocarbon such as benzene or toluene
  • an ether such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or 1,4-dioxane
  • an ester such as ethyl acetate
  • a halogenated hydrocarbon such as dichloromethane or 1,2-dichloroethane
  • an amide such as dimethylformamide or dimethylacetamide
  • inert solvents may be used alone or in combination as a mixture.
  • base usually, it is preferred to use as the base, from 1 to 2 equivalents of an organic base such as triethylamine or pyridine and as a solvent an aromatic hydrocarbon such as benzene or toluene, or an ether such as tetrahydrofuran or diethyl ether.
  • the reaction temperature may be set at an optional level within a range of from -60°C to the reflux temperature of the reaction mixture. However, it is preferred to conduct the reaction within a range of from 0°C to reflux temperature of the reaction mixture.
  • the base to be used in Process 3 may, for example, be the same as used in Process 2.
  • the solvent to be used may be any solvent so long as it does not hinder the reaction.
  • it may be a lower alcohol such as methanol or ethanol, an aromatic hydrocarbon such as benzene or toluene, an ether such as diethyl ether, 1,2- dimethoxyethane, tetrahydrofuran or 1,4-dioxane, an ester such as ethyl acetate, a ketone such as acetone or methyl ethyl ketone, a halogenated hydrocarbon such as
  • dichloromethane or 1,2-dichloroethane an amide such as dimethylformamide or dimethylacetamide, acetonitrile, dimethylsulfoxide, or water.
  • amide such as dimethylformamide or dimethylacetamide, acetonitrile, dimethylsulfoxide, or water.
  • inert solvents may be used alone or in combination as a mixture.
  • reaction temperature can be set at an optional level within a range of from -60°C to the reflux temperature of the reaction mixture. However, it is preferred to conduct the reaction at a temperature of from 0°C to 90°C.
  • a compound of the formula (VIII) can be obtained by reacting a compound of the formula (VII) and diphosphorus pentasulfide in an inert solvent or without solvent, or by reacting a compound of the formula (VII) with a
  • the compound of the formula (X) and a compound of the formula (XI) are reacted in an inert solvent in the presence or absence of a base to obtain a compound of the formula (XII) (a compound of the formula (I) of the present invention wherein R 3 is a hydrogen atom).
  • the compound of the formula (X) can also be obtained by reacting the compound of the formula (IX) to the compound of the formula (III) obtained in Process 1 of Method A.
  • the solvent to be used in Process 1 may be any solvent so long as it does not hinder the reaction.
  • it may be an aromatic hydrocarbon such as benzene or toluene, an ether such as diethyl ether, 1,2- dimethoxyethane, tetrahydrofuran or 1,4-dioxane, an ester such as ethyl acetate, a halogenated hydrocarbon such as dichloromethane or 1,2-dichloroethane, an amide such as dimethylformamide or dimethylacetamide, acetonitrile, pyridine, dimethylsulfoxide, or water.
  • aromatic hydrocarbon such as benzene or toluene
  • an ether such as diethyl ether, 1,2- dimethoxyethane, tetrahydrofuran or 1,4-dioxane
  • an ester such as ethyl acetate
  • a halogenated hydrocarbon such as dichloromethane or
  • reaction temperature can be set at an optional level within a range of from 0°C to the reflux temperature of the reaction mixture. However, it is preferred to conduct the reaction at a temperature of from 60°C to the reflux temperature.
  • the solvent to be used for Process 2 may be any solvent so long as it does not hinder the reaction.
  • a lower alcohol such as methanol or ethanol
  • an aromatic hydrocarbon such as benzene or toluene
  • an ether such as diethyl ether, 1,2-dimethoxyethane
  • dichloromethane or 1,2-dichloroethane an amide such as dimethylformamide or dimethylacetamide, acetonitrile, pyridine, dimethylsulfoxide or water, may be mentioned.
  • amide such as dimethylformamide or dimethylacetamide, acetonitrile, pyridine, dimethylsulfoxide or water.
  • solvents may be used alone or in combination as a mixture of two or more of them.
  • a copper salt such as copper chloride may, for example, be mentioned.
  • the reaction temperature may be set at any optional level from 0°C to the reflux temperature of the reaction mixture. However, it is usually preferred to conduct the reaction, for example, at a temperature within a range of from 60°C to the reflux temperature in ethanol.
  • the base and the solvent to be used in Process 3 may be the same as used in Process 2 in Method A.
  • the reaction temperature can be set at an optional level within a range of from 0°C to the reflux temperature of the reaction mixture. However, it is preferred to conduct the reaction at a temperature of from 0°C to 50°C.
  • a compound of the formula (XV) can be obtained by reacting a compound of the formula (XIII) (an
  • the base to be used in Process 1 may be the same as used in Process 2 in Method A.
  • the solvent to be used may be the same as used in Process 3 in Method A.
  • a base for example, from 1 to 3 equivalents, based on the substrate.
  • the reaction temperature may be set at any optional level from -60°C to the reflux temperature of the
  • reaction mixture it is preferred to conduct the reaction within a range of from 0°C to 90°C.
  • Processes 2 and 3 can be carried out in the same manner as in Method B.
  • a compound of the formula (XIX) can be obtained by reacting a compound of the formula (XVIII) with phosgene or a phosgene equivalent (phosgen dimer or triphosgene), if necessary in the presence of a suitable base.
  • the base to be used in Process 1, may be the same as used in Process 2 in Method A.
  • the solvent to be used may be any solvent so long as it does not hinder the reaction.
  • an organic solvent such as an organic solvent so long as it does not hinder the reaction.
  • an organic solvent such as an organic solvent so long as it does not hinder the reaction.
  • an organic solvent to be used such as an organic solvent so long as it does not hinder the reaction.
  • aromatic hydrocarbon such as benzene or toluene
  • an ether such as diethyl ether, 1,2-dimethoxyethane, ethylene glycol dimethyl ether, tetrahydrofuran or 1,4-dioxane
  • an ester such as ethyl acetate
  • a halogenated hydrocarbon such as dichloromethane or 1,2-dichloroethane
  • an amide such as dimethylformamide or dimethylacetamide
  • acetonitrile or pyridine
  • solvents may be used alone or in combination as a mixture of two or more of them.
  • the reaction temperature may be set at an optional level from 0°C to the reflux temperature of the reaction mixture. However, it is preferred to carry out the reaction within a range of from 0°C to 25°C.
  • the base to be used in Process 2 may be the same as used in Process 2 in Method A.
  • the solvent to be employed may be the same as used in Process 1 of this method.
  • the reaction temperature may be set at any optional level from 0°C to the reflux temperature of the reaction mixture. However, it is preferred to carry out the reaction within a range of from 0 to 25°C.
  • a compound of the formula (XII) of the present invention can be obtained by reacting a compound of the formula (XX) of the present invention and a compound of the formula (XXI) in the presence of a base in an inert solvent. Then, the compound of the formula (XII) of the present invention and a compound of the formula (XXII) are reacted in the presence of a base in an inert solvent to obtain a compound of the formula (I) of the present invention.
  • the base to be used in this reaction may, for example, be the same as used in Process 2 in Method A.
  • the solvent to be used may be any solvent so long as it does not hinder the reaction.
  • it may be the same as in Process 3 in Method A.
  • the reaction temperature can be set at an optional level within a range of from -60°C to the reflux temperature of the reaction mixture. However, it is preferred to conduct the reaction at a temperature of from 0°C to 90°C.
  • a compound of the formula (I) of the present invention can be obtained without isolating the compound of the formula (XII) by using two equivalents of the compound of the formula (XXI) and two equivalents of a base.
  • the compound of the formula (XV) can be prepared from the compound of the formula (XXIII) or
  • the suitable solvent to be used for this reaction may, for example, be an ether such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or 1,4-dioxane, or a phosphoric amide such as hexamethylphosphoric triamide. These solvents may be used alone or in combination as a mixture of two or more of them.
  • the reaction temperature can be set at an optional level from -78°C to the reflux temperature of the
  • reaction mixture it is preferred to carry out the reaction within a range of from -78°C to 25°C.
  • the compound of the formula (XXIII) wherein Q is Q-5, Q-14, Q-18 or Q-22 may be reacted with a compound of the formula (XXV) in a solvent inert to the reaction, if necessary in the presence of a suitable base, to obtain a compound of the formula (XIII) wherein Q is Q-5, Q-14, Q-18 or Q-22.
  • the base to be used for this reaction may be the same as used in Process 2 in Method A.
  • the solvent to be used may be the same as used in Process 3 in Method A.
  • reaction in a solvent such as tetrahydrofuran or dichloromethane without using any base, or to carry out the reaction by firstly preparing an alkali metal salt by using as a base from 0.01 to 2 equivalents, based on the substrate, of an organic base such as triethylamine, or from 1 to 2 equivalents, based on the substrate, of sodium hydride or the like.
  • a solvent such as tetrahydrofuran or dichloromethane
  • organic base such as triethylamine
  • the reaction temperature may be set at an optional level from -20°C to the reflux temperature of the
  • the base to be used for this reaction may, for example, be an alkali metal carbonate such as sodium carbonate, potassium carbonate or sodium
  • an alkali metal hydride such as sodium hydride or potassium hydride
  • an organic base such as triethylamine or pyridine.
  • the solvent to be used may be any solvent so long as it does not hinder the reaction.
  • an organic solvent such as an organic solvent so long as it does not hinder the reaction.
  • an organic solvent such as an organic solvent so long as it does not hinder the reaction.
  • aromatic hydrocarbon such as benzene or toluene
  • an ether such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or 1,4-dioxane
  • an ester such as ethyl acetate
  • a halogenated hydrocarbon such as
  • dichloromethane or 1,2-dichloroethane an amide such as dimethylformamide, dimethylacetamide, acetone,
  • acetonitrile or water
  • solvents may be used alone or in combination as a mixture of two or more of them.
  • the base usually, it is preferred to employ as the base from 1 to 3 equivalents, based on the substrate, of an organic base such as triethylamine or pyridine in a solvent such as tetrahydrofuran, ethyl acetate, dichloromethane or benzene.
  • the reaction temperature may be set at any optional level from -60°C to the reflux temperature of the reaction mixture. However, it is preferred to carry out the reaction within a range of from 0 to 120°C.
  • the compound of the formula (VII) wherein R 1 ⁇ H can be produced also by reacting a compound of the formula (II) which can be produced by reacting the compound of the formula (XXVI) and the compound of the formula (XXVIII) in the same manner, with a compound of the formula (VI), if necessary in the presence of a base in a solvent inert to the reaction.
  • the base to be used here may be the same as used in Process 2 in Method A.
  • the solvent to be used may be the same as used in Process 3 is Method A.
  • the base usually, it is preferred to use as the base from 1 to 3 equivalents, based on the substrate, of sodium hydride, potassium hydride, potassium tert-butoxide or potassium hydroxide in a polar solvent such as tetrahydrofuran or dimethylformamide, or to use as the base from 1 to 3 equivalents, based on the substrate, of potassium
  • the reaction temperature may be set at an optional level of from -60°C to the reflux temperature of the reaction mixture. However, it is preferred to carry out the reaction within a range of from 0 to 90°C.
  • the catalyst to be used in this reaction may, for example, be an organic base such as triethylenediamine or diazabicycloundecene.
  • the amount of the catalyst to be used can be set at an optional level within a range of from 0.001 wt% to 10 wt%, relative to the compound of the formula (XI).
  • the solvent may be any solvent so long as it does not hinder the reaction.
  • it may be an aromatic hydrocarbon such as benzene or toluene, an ether such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or 1,4-dioxane, an ester such as ethyl acetate, a
  • halogenated hydrocarbon such as dichloromethane
  • the reaction temperature can be set at an optional level within a range of from -60°C to the reflux temperature of the reaction mixture. However, it is preferred to conduct the reaction at a temperature of from 0°C to 50°C. In this reaction, the molar ratio of the reactants is not particularly limited. However, in order to obtain the compound of the formula (XXIX) in good yield, it is preferred to employ the compound of the formula (IX) in a slightly excess amount relative to the compound of the formula (XI).
  • a compound of the formula (XXXI) can be obtained by reacting a compound of the formula (XXX) and a compound of the formula (XI) in the presence or absence of a catalyst in an inert solvent.
  • the catalyst, the solvent and the reaction conditions such as the temperature to be used in this reaction may be similar to those in
  • the compound of the formula (XXIX) can be obtained in good yield by using equimolar amounts of the compound of the formula (XXX) and the compound of the formula (XI).
  • the acid to be used may, for example, be an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as
  • the solvent may be any solvent so long as it does not hinder the reaction.
  • it may be a lower alcohol such as methanol or ethanol, an aromatic hydrocarbon such as benzene or toluene, an ether such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or 1,4-dioxane, an ester such as ethyl acetate, a halogenated hydrocarbon such as dichloromethane, carbon tetrachloride or 1,2-dichloroethane, an amide such as dimethylformamide or dimethylacetamide, acetonitrile, dimethylsulfoxide, acetic acid, or water.
  • These inert solvents may be used alone or in combination as a mixture. Usually, it is preferred to employ from 1 to 50 equivalents of
  • the reaction temperature can be set at an optional level within a range of from -60°C to the reflux temperature of the reaction mixture. However, it is preferred to conduct the reaction at a temperature of from 0°C to the reflux temperature of the reaction mixture.
  • the molar ratios of the respective reactants are not particularly limited.
  • the compound of the present invention can be separated and purified by an optional purification method such as recrystallization, column chromatography or thin layer chromatography.
  • a suitable carrier for example, a solid carrier such as clay, pulp, bentonite, diatomaceous earth or fine silica powder, or a liquid carrier such as water, an alcohol (such as isopropanol, butanol, benzyl alcohol or furfuryl alcohol), an aromatic hydrocarbon (such as toluene or xylene), an ether (such as anisol), a ketone (such as cyclohexanone or isophorone), an ester (such as butyl acetate), an acid amide (such as N-methylpyrrolidone) or a halogenated hydrocarbon (such as chlorobenzene).
  • thickener an anti-freezing agent, an anti-solidification agent and/or a stabilizer may be added. It may be practically used in the form of an optional formulation such as a liquid formulation, an emulsifiable
  • the compound of the present invention may be mixed with various other herbicides, insecticides, miticides, nematocides, fungicides, plant growth regulating agents, synergists, fertilizers or soil improving agents, as the case requires.
  • the dose in application of the compound of the present invention varies depending upon the application site, the application season, the manner of application and the type of the crop plant. However, it is usually in an amount of from 0.005 to 50 kg/ha as the amount of active ingredient.
  • an antisolidification agent may, for example, be mentioned.
  • an antifreezing agent and a thickener may, for example, be mentioned.
  • the compounds of the present invention were prepared or can be prepared in accordance with the following
  • pentasulfide were added to 30 ml of pyridine, and the mixture was stirred for 2 hours under reflux under heating and then added to 300 ml of ice water.
  • the mixture was made alkaline by an addition of an aqueous sodium hydroxide solution and then extracted with 200 ml of ethyl acetate.
  • the organic layer was washed twice with dilute hydrochloric acid and dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure. The residue was washed with
  • isothiocyanate was dropwise added thereto.
  • the mixture was returned to room temperature, and then the stirring was further continued overnight.
  • 30 ml of 1N HCl was added to the reaction solution, and the mixture was extracted with 200 ml of ethyl acetate.
  • the organic layer was washed with water and dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure. The residue was washed with
  • Ethyl 2-aminothiazole-4-carboxylate was added to a mixture comprising 30 ml of concentrated hydrochloric acid and 10 ml of phosphoric acid, and the mixture was stirred under cooling with ice. Then, 10 ml of an aqueous solution containing 1.6 g of sodium nitrite was dropwise added thereto. After completion of the dropwise addition, stirring was further continued for 4 hours at room temperature. The mixture was dropwise added to 50 ml of chloroform having 1.90 g of copper chloride
  • 2-chlorothiazole-4-carboxylic acid was converted to 2-chlorothiazole-4-carboxylic acid chloride by means of thionyl chloride. Then, 10 ml of a dichloromethane solution thereof was dropwise added to 50 ml of a
  • tetrahydrofuran solution containing 1.5 g of pyrrole was dropwise added with stirring at room temperature. After completion of the dropwise addition, the mixture was stirred for one hour at room temperature. Then, 20 ml of a tetrahydrofuran solution containing 3.2 g of
  • hydrazine monohydrate was added to 5 ml of an ethanol solution containing 0.48 g of methyl N-(4-cyanophenyl)pyrrole-1-thioimidate, and the mixture was stirred for 1.5 hours at room temperature. Then, 5 ml of ethanol was further added thereto, and the mixture was stirred overnight. Then, 20 ml of ethyl acetate was added to the reaction mixture, and the mixture was washed with water and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was dissolved in 5 ml of tetrahydrofuran, and 0.5 g of 4-trifluoromethylphenyl isocyanate was added
  • the compounds of the present invention can be synthesized in accordance with the above described production methods and Examples. Specific examples of such compounds are shown in Tables 6 to 9. However, it should be understood that the present invention is by no means restricted to such specific Examples.
  • Compound of the present invention 50 parts Zeeklite PFP (tradename for Kaoline-type clay, manufactured by Zeeklite Mining Industries Co., Ltd.)
  • Sorpol 5050 (tradename for anionic surfactant, manufactured by Toho Chemicals Ind. Co., Ltd.)
  • Lunox 1000C (tradename for anionic surfactant, manufactured by Toho Chemicals Ind. Co., Ltd.)
  • Carplex #80 antioxidant (tradename for fine silica, manufactured by Shionogi & Co., Ltd.)
  • Sorpol 3005X (tradename for a mixture of a nonionic surfactant and an anionic surfactant, manufactured by Toho Chemicals Ind. Co., Ltd.)
  • Agrisol S-711 (tradename for a nonionic surfactant, manufactured by Kao Corporation)
  • Lunox 1000C (tradename for anionic surfactant, manufactured by Toho Chemicals Ind. Co., Ltd.)
  • Rodopol water (tradename for a thickener,
  • the above components are uniformly mixed to obtain a flowable.
  • Compound of the present invention 75 parts Isoban No. 1 (tradename for an anion surfactant, manufactured by Kuraray Isoprene Chemical K.K.)
  • Anilex N (tradename for anionic surfactant,
  • Carplex #80 (tradename for fine silica, manufactured by Shionogi & Co., Ltd.)
  • the above components are uniformly mixed and finely pulverized to obtain a dry flowable.
  • the above components are uniformly mixed and triturated. Then, a small amount of water is added thereto. The mixture is stirred, kneaded and then granulated by an extrusion-type granulator, followed by drying to obtain a granule.
  • Carplex #80 (tradename for fine silica, manufactured by Shionogi & Co., Ltd.)
  • the above wettable powder, emulsifiable concentrate, flowable or dry flowable is diluted from 50 to 20,000 times with water and applied so that the active ingredient will be from 0.05 to 50 kg/ha.
  • 5% emulsifiable concentrates of the compounds of the present invention (25% wettable powders in the case of certain compounds) were diluted with water containing a spreader to prepare the samples of liquid insecticides with a concentration of 1,000 ppm. Leaves of cabbage were immersed in the respective samples of liquid
  • insects per dish 10 insects per dish.
  • the dishes were closed with a perforated cover and kept in a 25°C thermostatic chamber.
  • the percentage of mortality of the insects after the lapse of 6 days was calculated by the following formula. The tests were conducted twice for each compound.
  • TEST EXAMPLE 2 Insecticidal test on twenty eight-spotted ladybird (Epilachna vigintioctopunctata)
  • 5% emulsifiable concentrates of the compounds of the present invention (25% wettable powders in the case of certain compounds) were diluted with water containing a spreader to prepare the samples of liquid insecticides with a concentration of 1,000 ppm. Leaves of tomato were immersed in the respective samples of liquid insecticides for about 10 seconds. Then, after air drying the leaves, they were placed in the Petri dishes and the second instar nymphae of twenty eight-spotted ladybird

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

Abstract

Dérivé de semicarbazone représenté par la formule (I) ou son sel et pesticide contenant ledit dérivé. Dans la formule (I), Q représente Q-1, Q-2 ou similaire, J représente J-1, J-2 ou similaire, G représente G-1, G-2 ou similaire, W représente un atome d'oxygène ou un atome de soufre; chacun de X, Y et Z, indépendants les uns des autres, représente un atome d'hydrogène, un atome d'halogène, un groupe alkyle C1-6, un groupe haloalkyle C1-6 ou similaire, k est un entier de 0 à 5, à condition que, quand k est de 2 à 5, la pluralité de X peut être similaire ou différente; m est un entier de 0 à 5, à condition que, quand m est de 2 à 5, la pluralité de Y peut être similaire ou différente; n est un entier de 0 à 5, à condition que, quand n est de 2 à 5, la pluralité de Z peut être similaire ou différente; chacun de R?1, R2 et R3¿, qui sont indépendants les uns des autres, représente un atome d'hydrogène, un groupe alkyle C¿1-6?, un groupe haloalkyle C1-6, un groupe haloalkényle C2-6.
PCT/JP1996/002022 1995-07-21 1996-07-19 Derives de semicarbazone et pesticides WO1997003976A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU64703/96A AU6470396A (en) 1995-07-21 1996-07-19 Semicarbazone derivatives and pesticides

Applications Claiming Priority (4)

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JP7/185814 1995-07-21
JP18581495 1995-07-21
JP14837996 1996-05-17
JP8/148379 1996-05-17

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7094807B2 (en) 2002-11-19 2006-08-22 Achillion Pharmaceuticals, Inc. Substituted aryl thioureas and related compounds; inhibitors of viral replication
US7767706B2 (en) 2004-05-18 2010-08-03 Achillion Pharmaceuticals, Inc. Substituted aryl acylthioureas and related compounds; inhibitors of viral replication
CN104163792A (zh) * 2013-05-20 2014-11-26 湖南化工研究院 N-吡啶酰胺类化合物及其制备方法与应用
WO2014187297A1 (fr) * 2013-05-20 2014-11-27 湖南化工研究院有限公司 Composé de n-pyridine-amide (hétéro)aromatique et procédé pour le préparer et l'utiliser
US11884682B2 (en) * 2020-06-23 2024-01-30 Nanjing Immunophage Biotech Co., Ltd. Compounds and their uses as MIF inhibitors

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JPH07165697A (ja) * 1993-10-04 1995-06-27 Nissan Chem Ind Ltd セミカルバゾン化合物及び有害生物防除剤

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CHEMICAL ABSTRACTS, vol. 117, no. 25, 1992, Columbus, Ohio, US; abstract no. 251312, L.S. SAMOILENKO ET AL.: "Synthesis of substituted 2-amino-4-methylpyrimidine based on the arylamides of alpha-phenylaminomethylidene-beta-ketothiobutyric acid" page 688; column 1; XP002016751 *
CHEMICAL ABSTRACTS, vol. 124, no. 7, 19 February 1996, Columbus, Ohio, US; abstract no. 86903, B. MODZELWSKA: "The reaction of N3-substituted amidrazones of 4-picoline with isothiocyanates" page 1304; column 1; XP002016750 *
CHEMICAL ABSTRACTS, vol. 95, no. 1, 1981, Columbus, Ohio, US; abstract no. 7159, T. BANY ET AL.: "Synthesis of some derivatives of 1,2,4-triazole and 1,3,4-thiadiazole using N3-substituted amidrazones as starting materials" page 678; column 1; XP002016752 *
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7094807B2 (en) 2002-11-19 2006-08-22 Achillion Pharmaceuticals, Inc. Substituted aryl thioureas and related compounds; inhibitors of viral replication
US7476686B2 (en) 2002-11-19 2009-01-13 Achillion Pharmaceuticals, Inc. Substituted aryl thioureas and related compounds; inhibitors of viral replication
US7767706B2 (en) 2004-05-18 2010-08-03 Achillion Pharmaceuticals, Inc. Substituted aryl acylthioureas and related compounds; inhibitors of viral replication
CN104163792A (zh) * 2013-05-20 2014-11-26 湖南化工研究院 N-吡啶酰胺类化合物及其制备方法与应用
WO2014187297A1 (fr) * 2013-05-20 2014-11-27 湖南化工研究院有限公司 Composé de n-pyridine-amide (hétéro)aromatique et procédé pour le préparer et l'utiliser
US11884682B2 (en) * 2020-06-23 2024-01-30 Nanjing Immunophage Biotech Co., Ltd. Compounds and their uses as MIF inhibitors

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