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EP0228447A1 - Derives de polyhaloalcene a effet pesticide - Google Patents

Derives de polyhaloalcene a effet pesticide

Info

Publication number
EP0228447A1
EP0228447A1 EP86904515A EP86904515A EP0228447A1 EP 0228447 A1 EP0228447 A1 EP 0228447A1 EP 86904515 A EP86904515 A EP 86904515A EP 86904515 A EP86904515 A EP 86904515A EP 0228447 A1 EP0228447 A1 EP 0228447A1
Authority
EP
European Patent Office
Prior art keywords
trifluoro
compound
effective amount
butenylthio
acceptable carrier
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP86904515A
Other languages
German (de)
English (en)
Other versions
EP0228447A4 (en
Inventor
Thomas Gerard Cullen
Anthony Joseph Martinez
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
FMC Corp
Original Assignee
FMC Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by FMC Corp filed Critical FMC Corp
Publication of EP0228447A1 publication Critical patent/EP0228447A1/fr
Priority to MYPI87002201A priority Critical patent/MY102076A/en
Publication of EP0228447A4 publication Critical patent/EP0228447A4/en
Ceased legal-status Critical Current

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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
    • C07D207/34—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 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/42—Halogenated unsaturated alcohols acyclic
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/42—Halogenated unsaturated alcohols acyclic
    • C07C33/423—Halogenated unsaturated alcohols acyclic containing only double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/16—Isothiocyanates
    • C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
    • C07C331/22—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/63—Halogen-containing esters of saturated acids
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    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D207/34—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 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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    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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    • C07D221/06—Ring systems of three rings
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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D277/16—Sulfur atoms
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    • 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
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    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
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    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • 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
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    • 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
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    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring

Definitions

  • This invention relates to pesticidal polyhaloalkene derivatives and use for combatting infestations of nematodes in soil and in plant systems, particularly agricultural crops, and for combatting plant- destructive diseases caused whol ly or in part by nematodes .
  • the i nvent ion further concerns anthelmintic applications of the compounds.
  • U.S. Patent 3,513,172 - Brokke and divisional patents thereof disclose nematicidal trifluorobutenyl derivatives of the formula
  • F 2 C CFCH 2 CH 2 -R
  • R is selected from various substituents including some heterocyclics such as 2-thio-4-alkylthiazolyl.
  • a new class of polyhaloalkene derivatives has now been found having high nematicidal activity and good soil mobility.
  • the compounds exhibit control of a variety of nematodes, and in some cases systemic activity.
  • the compounds also are effective against helminths that are indicators of animal anthelmintic activity.
  • novel nematicidal compounds of the invention are polyhaloalkene derivatives of the formula (I): wherein X is sulfur, oxygen, nitrogen or methylene, Y 1 and Y 2 independently are fluorine, chlorine or bromine, Z is hydrogen or the same as Y 1 or Y 2 , and n is 1-4, preferably 1 or 2; provided that: (A) when X is. sulfur, R is thiazolyl, optionally substituted thienyl, optionally substituted thianaphthyl, optionally substituted thiazolinyl, optionally substituted thiadiazolyl, optionally substituted oxadiazolyl or 3,4,4-trifluoro-3-butenyloxycarbonyl- methyl;
  • R when X is oxygen, R is C(O)R 1 wherein R 1 is perfluoroalkyl, optionally substituted phenyl, optionally substituted thienyl, optionally substituted furanyl, optionally substituted pyrrolyl or dihydro- thiazolylthiomethyl;
  • Other aspects of the invention include methods of controlling nematode populations and arresting plant and animal diseases caused by nematodes and helminths, and nematicidal and anthelmintic formulations based on the polyhaloalkene derivatives.
  • Typical nematode species controlled in accordance with the invention are the root-knot, stunt, lesion, cyst and C. elegans nematodes.
  • available carbon atoms of the heterocyclic rings other than thiazolyl optionally may be substituted with any group or groups which are non-destruc tive of the nematicidal or anthelmintic activity of the compounds.
  • Typical substituents include aliphatic, aromatic and heterocyclic groups, halo, nitro, cyano, alkoxy, alkylthio, haloalkyl, haloalkoxy, halo-, nitro-, cyano- or alkoxy-substituted phenyl, polyhaloalkenylthio, phenylalkylthio, phenylthioalkylthio, propargylthio, cycloalkylmethylthio, and the like, further including straight and branched chain structures, and the various isomers of such substituents.
  • alkyl, alkenyl and alkynyl groups may contain 1-11 or more carbon atoms and may be straight. chain or branched. Cycloalkyl groups may contain 3-8 or more carbon atoms.
  • alkyl, alkenyl, alkynyl and alkoxy are lower alkyl, lower alkenyl, lower alkynyl or lower alkoxy, meaning that these groups contain 1-8 carbon atoms, more preferably 1-4 carbon atoms such as methyl, propenyl and methoxy.
  • Halo or halogen means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
  • Aromatic substituents include phenyl, naphthyl, anthracene, diphenyl, and the like.
  • R is a thiadiazolyl group of the structure:
  • R 2 is 3,4,4-trifluoro-3-butenyl, or a phenylmethyl or phenylthiomethyl group each optionally substituted with halogen or nitro.
  • the R 2 S- group may be in the 3- or 5-position of the 1,2,4-thiadiazole ring;
  • R is a thiadiazolyl group as in (1) above but with lodo in place of R 2 S;
  • R is a thiadiazolyl group of the structure:
  • R 3 is aryl, arylalkyl, aryloxyalkyl, alkylthio, haloalkylthio, cyanoalkylthio, arylalkylthio, aryloxyalkylthio, arylthioalkylthio, heterocycloalkylthio, alkenylthio, haloalkenyl- thio, halocycloalkylalkenylthio, or an amino group mono- or disubstituted with members selected independently from alkyl, alkylcarbonyl, haloalkylcarbonyl, aryl, arylaminocarbonyl, arylalkylcarbonyl, arylalkoxycarbonyl and 3-(2,2-di- chloroethenyl)-2,2-dimethylcyclopropanecarbonyl;
  • R is an oxadiazolyl group of the structure:
  • R 4 is aryl or arylalkyl substituted with chloro, fluoro, alkyl, haloalkyl, alkoxy, or nitro.
  • the R 4 group may be in the 3- or 5- position of the 1,2,4-oxadiazole ring; or
  • R is an oxadiazolyl group of the structure:
  • R 5 is alkyl, haloalkyl, aryl, arylalkyl, aryloxyalkyl, arylthioalkyl, heterocyclo- alkyl, arylalkenyl or alkynyl (C 2 -C 11 ).
  • Aryl and the heterocycles described in (3) and (4) above are optionally substituted with one or more groups selected independently from halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano, nitro and phenyl.
  • Aryl and the heterocycles described in (5) above are optionally substituted with one or more groups selected independently from halogen, alkyl, alkoxy, nitro, amino, hydroxy, acetyloxy and alkylaminocarbonyloxy.
  • R is a thiazolyl group.
  • the compounds of formula I are prepared in a known manner. For example, a polyhaloalkene such as 4-bromo-1,1,2-trifluoro-1-butene is reacted with a mercaptothiazole (prepared by reaction of thiazole and elemental sulfur) or mercaptothiazoline in a reaction solvent medium containing sodium ethoxide to form the thiazolyl or thiothiazoline derivative of the polyhaloalkene.
  • Compounds of formula I wherein X is oxygen (subclass B) may be prepared as described in Examples 3 and 4.
  • polyhaloalkenes may be used in known ways to prepare other compounds of formula I.
  • trifluoroethylene can be chain-extended with methyl dibromide and the 1,3-dibromo-1,1,2-trifluoropropane product then reacted with a mercaptan to form a thio intermediate.
  • the intermediate is then dehydrohalo- genated, as follows, wherein "BP” is benzoyl peroxide and "DBU” is 1,8-diazabicyclo[5.4.0]undec-7-ene catalyst, as described by Tarrant and Tandon, J. Org. Chem. 34(4), 864 (1969): 2 2
  • Dihalopropene derivatives within the scope of formula I may be prepared by the following general reaction, wherein Y 1 and Y 2 are as defined above and one of Y 1 and Y 2 also may be hydrogen:
  • Trihalopropene derivatives also may be prepared in a manner and reaction similar to the Tarrant and Tandon scheme to form other compounds of formula I, wherein Y and Z are as defined in formula I
  • Examples 1-9 correspond to compounds 1-9 listed in Tables 1 and lb.
  • Examples 10-17 identify the tabulated compounds to which they relate.
  • ethoxide was prepared by stirring 0.25 gram (0.011 mole) of sodium metal in 30 ml of absolute ethanol. To this was added 1.2 grams (0.01 mole) of 2-mercaptothiazoline. The reaction mixture was stirred for one hour and the excess ethanol was removed under reduced pressure. The residue was dissolved in 35 ml of methyl ethyl ketone and 2.0 grams (0.01 mole) of 4-bromo-1,1,2-trifluoro-1-butene was added. The reaction mixture was stirred at ambient temperature for four hours, then concentrated under reduced pressure to a residue. The residue was dissolved in 50 ml of toluene and washed with three 25 ml portions of water.
  • Example 4 (3,4,4-Trifluoro-3-butenyl) 4-chlorobenzoate To a stirred solution of 1.6 grams (0.01 mole) of 4-chlorobenzoic acid in 35 ml of acetonitrile was added 1.5 ml (0.01 mole) of 1,8-diazabicyclo[5.4.0]- undec-7-ene, followed by 1.9 grams (0.01 mole) of 4-bromo-1,1,2-trifluoro-1-butene. The reaction mixture was heated under reflux for four hours then allowed to cool to ambient temperature. Water, 25 ml, was added to the reaction mixture, and the reaction mixture was extracted with three 20 ml portions of diethyl ether.
  • Example 5 N-(3,4,4-trifluoro-3-butenyl)succinimide This compound was prepared in a manner analogous to that of Example 1 using 1.1 grams (0.01 mole) of succinimide, 1.9 grams (0.01 mole) of 4-bromo-1,1,2- trifluoro-1-butene, 0.25 gram (0.01 mole) of sodium metal, 30 ml of absolute ethanol and 20 ml of di- methylformamide. The yield of N-(3,4,4-trifluoro-3- butenyl) succinimide was 0.3 gram as an oil. The nmr and the ir spectra were consistent with the proposed structure.
  • Example 6 (3,4,4-Trifluoro-3-butenyl)isothiocyanate (A) To a stirred solution of 10.0 grams (0.053 mole) of 4-bromo-1,1,2-trifluoro-1-butene in 50 ml of dimethylformamide was added 10.4 grams (0.056) of the commercially available potassium salt of phthalimide. The reaction mixture was warmed to 50°C where it stirred for four hours. The reaction mixture was allowed to cool and 50 ml of chloroform was added. The mixture was poured into 200 ml of water. The aqueous layer was separated and extracted with two 50 ml portions of chloroform.
  • Example 7 4,5,5-Trifluoro-4-penten-1-ol (A) To a stirred mixture of 2.4 grams (0.1 mole) of magnesium turnings in 100 ml of diethyl ether was added 18.9 grams (0.1 mole) of 4-bromo-1,1,2-tri- fluoro-1-butene. Upon completion of addition the reaction mixture was heated under reflux until the reaction was complete. The reaction mixture was cooled to 0oC and 9.0 grams (0.2 mole) of carbon dioxide was bubbled in slowly. Upon completion of addition the reaction mixture was stirred for one hour, then 100 ml of aqueous 20% hydrochloric acid was added to destroy the excess magnesium. The reaction mixture was extracted with three 40 ml portions of diethyl ether.
  • Example 8 3-Chloro-5-(3,4,4-trifluoro-3- butenylthio)-1,2,4-thiadiazole
  • reaction mixture Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred for 16 hours. The reaction mixture was concentrated under reduced pressure to a residual solid. The solid was dissolved in ethyl acetate and filtered. The filtrate was concentrated under reduced pressure, and the residual solid dried in a vacuum oven. The dried solid was dissolved in hot chloroform - ethyl acetate and filtered. The filtrate was concentrated under reduced pressure, and the residual solid dried in a vacuum oven to give 4.4 grams of potassium (3,4,4-trifluoro-3-butenyl) cyanoimidodithiocarbonate. The nmr spectrum was consistent with the proposed structure.
  • 1,2,4-dithiazol-3-thione was added portionwise. After all of the 5-amino intermediate was in solution, 4.7 grams (0.027 mole) of 4-nitrophenylmethyl chloride was added dropwise. Upon completion of addition the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in 20 ml of water then extracted with two 25 ml portions of diethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid to yield a gummy solid. The solid was extracted from the aqueous layer with two 25 ml portions of ethyl acetate. The combined extracts were dried with sodium sulfate and filtered.
  • Example 12 2-(1-Methylethylthio)-5-(3,4,4-trifluoro-3- butenylthio)-1,3,4-thiadiazole
  • a solution of 22.5 grams (0.15 mole) of 2,5-di- mercapto-1,3,4-thiadiazole in 200 ml of tetrahydrofuran was stirred and 21 ml (0.15 mole) of triethyl- amine was added dropwise.
  • the reaction mixture was stirred at ambient temperature for 15 minutes, then 28.4 grams (0.15 mole) of 4-bromo-1,1,2-trifluoro-1-butene was added dropwise.
  • the reaction mixture was heated under reflux for two hours.
  • the cooled reaction mixture was concentrated under reduced pressure to a residue.
  • the residue was stirred in 250 ml of diethyl ether and extracted with two 100 ml portions of aqueous 10% potassium hydroxide.
  • the combined extracts were acidified with aqueous 10% hydrochloric acid, then were extracted with two 100 ml portions of diethyl ether.
  • the combined ether extracts were dried with sodium sulfate and filtered.
  • the filtrate was concentrated under reduced pressure to yield, after drying, 35.6 grams of 2-mercapto-5-(3,4,4-tri- fluoro-3-butenylthio)-1,3,4-thiadiazole as a solid.
  • the nmr spectrum was consistent with the proposed structure.
  • the extract was acidified with an aqueous 5% hydrochloric acid solution, and then was extracted with diethyl ether.
  • the ether extract was concentrated under reduced pressure to yield 0.3 gram of 2-(4-chlorophenyl)-5-mercapto-1,3,4-thiadiazole; m.p. 178°C.
  • reaction mixture Upon completion of addition the reaction mixture is stirred for three hours during which time it is allowed to warm to ambient temperature. The solvent is removed under reduced pressure. The residue is dissolved in diethyl ether and washed with two portions of an aqueous solution saturated with sodium chloride. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residual semi-solid. The semi-solid is subjected to column chromatography on silica gel. Elution is accomplished with 1:1 - hexane:diethyl ether. The appropriate fractions are combined and concentrated under reduced pressure to give 0.4 gram of 2-(3,4,4-trifluoro-3-butenylthio) thiazole as an oil. The nmr and ir spectra are consistent with the proposed structure.
  • Example 17 (Compound 231) Synthesis of 2-(2,3,3-trifluoro-2- propenylthio) thiazole (A) A stainless steel autoclave is charged with 50 grams (0.6 mole) of trifluoroethylene, 300 grams (1.7 moles) of dibromomethane, and 5 grams (0.02 mole) of benzoyl peroxide. The reaction mixture is stirred and heated at 100°C for six hours, then is cooled to -70oC. The autoclave is opened and the reaction mixture fractionally distilled. The appropriate fractions are combined to give 1,3-dibromo-1,1,2-tri- fluoropropane.
  • the reaction mixture is concentrated under reduced pressure to a residue.
  • the residue is dissolved in diethyl ether and is washed with two portions of aqueous sodium chloride.
  • the organic layer is dried with magnesium sulfate and filtered.
  • the filtrate is concentrated under reduced pressure to a residue.
  • the residue is purified by column chromatography to give 2-(3-bromo-2,3,3-trifluoropropylthio)- thiazole.
  • Tables la and lc the compounds are those of formula I wherein Y 1 , Y 2 and Z are fluoro, based upon the use of 4-bromo-1,1,2-trifluoro-1-butene as the starting material in the synthesis.
  • Pesticidal Use The compounds of the invention can be used against a variety of pests that attack plants and animals. In agriculture, they are useful as nematicides, particularly against plant-parasitic nematodes and "free-living" nematodes, i.e., nematodes not dependent on any specific plant or other host. An example of the latter is the microbivorous nematode Caenorhabditis elegans. This nematode will feed on bacteria such as Escherichia coli and is used as a screen for both agricultural and veterinary nematicides or anthelmintics.
  • the compounds When used as anthelmintics, in veterinary treatments for treatment of infestations of Ascaris lumbricoides (roundworm in pigs) for example, the compounds may be administered orally, parenterally or topically either alone but more usually in a pharmaceutically acceptable carrier, to provide an appropriate dosage .
  • a pharmaceutically acceptable carrier include one or more of water , gelati ne , sugars, starches, organic acids such as stearic or citric acid and salts thereof, talc, vegetable fats or oils, gums, glycols and other excipients, for administ ration as solids ( e . g . , tablets or capsules) or liquids (e.g., solutions, suspensions or emulsions).
  • compositions may also contain preservatives, stabilizers, wetting or emulsifying agents, buffers, salts and other therapeutic agents.
  • the compositions may be formulated by conventional methods to contain about 5 to 95% by weight of the anthelmintic compound, preferably about 25 to 75% by weight. Further guidance to anthelmintic activity, formulations and modes of treatment, utilizing the compounds of the invention, is available from publications on the subject, such as the article "Chemotherapeutics, Anthelmintic” in Kirk-Othmer, Encyclopedia of Chemical Technology, Third ed., 5 451-468, and articles cited therein, and in the patent literature, such as U.S. Patent 3,576,892, col. 3, lines 29-56.
  • the compounds are generally not applied full strength, but are formulated with agriculturally acceptable carriers and various additives normally employed for facilitating the dispersion of active ingredients, optionally with other active ingredients, recognizing that the formulation and mode of application of a toxicant may affect the activity of the material.
  • the present compounds may be applied, for example, as powders or liquids, the choice of application varying with the nematode species and environmental factors present at the particular locus of infestation.
  • the compounds may be formulated as granules, dusts, wettable powders, emu ⁇ sifiable concentrates, solutions, suspensions, dispersions, controlled release compositions, and the like.
  • a typical formulation may vary widely in concentration of the active ingredient depending on the particular agent used, additives, carriers or other active ingredients used, the nematode species to be controlled, and the desired mode of application.
  • the active ingredient of a typical formulation may, for example, suitably be present at a concentration of from about 0.5% up to about 99.5% by weight of the formulation.
  • Surface active agents, if employed in the formulation, may be present at various concentrations, suitably in the range of 1 to 30% by weight.
  • Dusts are admixtures of the active ingredient with finely divided solid carriers and/or diluents such as talc, natural clays, kieselguhr, pyrophyllite, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, and other organic and inorganic solid carriers.
  • finely divided formulations generally have an average particle size of less than about 50 microns (325 mesh, Standard U.S. Sieve Series).
  • the active ingredient will be present in dust formulations at a concentration in the range of 1 to 15%, and occasionally from 1% to about 30%, the balance of the composition typically comprising one or more agriculturally acceptable inerts as adjuvant, carrier, or diluent.
  • the nematicidal compounds of the invention may also be formulated as wettable powders. These formulations are in the form of finely divided particles which disperse readily in water or other liquid vehicles.
  • the wettable powder is ultimately applied as a dry dust or a dispersion in water or other liquid.
  • Typical carriers for wettable powders include fuller's earth, kaolin clays, silicas, and other highly absorbent or adsorbent inorganic diluents.
  • the concentration of active ingredient in wettable powders is dependent upon physical properties of the active ingredient and the absorbency of the carriers.
  • Liquids and low melting solids are suitably formulated in the concentration range of 5 to 50% by weight; usually 10 to 30%; high melting solids (mp greater than 100°C) being formulated in the range of 5 to 95% by weight, usually 50 to 85%.
  • Microencapsulated or other controlled release formulations may also be used for application of compounds in accordance with this invention.
  • Emulsifiable concentrates are homogeneous liquid compositions, usually containing the active ingredient dissolved in a liquid carrier.
  • Commonly used liquid carriers include xylene, heavy aromatic naphthas, isophorone, and other nonvolatile or slightly volatile organic solvents.
  • these concentrates are dispersed in water, or other liquid vehicle, forming an emulsion, and are normally applied as a spray to the area to be treated.
  • the concentration of the essential active ingredient in EC's may vary according to the manner in which the composition is to be applied, but, in general, is in the range of 0.5 to 95%, frequently 10 to 80%, by weight of active ingredient, with the remaining 99.5% to 5% being surfactant and liquid, carrier.
  • Flowables are similar to EC's except that the ingredient is suspended in a liquid carrier, generally water.
  • Flowables like EC's, may include a small amount of a surfactant, and contain active ingredient in the range of 0.5 to 95%, frequently from 10 to 50%, by weight of the composition.
  • flow- ables may be diluted in water or other. liquid vehicle, and are normally applied as a spray to the area to be treated.
  • Typical wetting, dispersing or emulsifying agents used in these formulations include, but are not limited to, the alkyl and alkylaryl sulfonates and sulfates and their sodium or calcium salts; alkylaryl polyether alcohols; sulfated higher alcohols; poly- ethylene oxides; sulfonated animal and vegetable oils; sulfonated petroleum oils; fatty acid esters of poly- hydric alcohols and the ethylene oxide addition products of such esters; addition products of long- chain mercaptans and ethylene oxide; and addition products of alkylphenols such as nonylphenol and ethylene oxide.
  • the surface-active agent when used, normally comprises from 1 to 15% by weight of the nematicidal composition;
  • compositions include simple solutions of the active ingredient in a relatively non-volatile solvent such as corn oil, kerosene, propylene glycol, or other organic solvents. This type of formulation is particularly useful for ultra-low volume application.
  • the concentration of active ingredient in use dilution is normally in the range of about 2% to about 0.1%.
  • Many variations of spraying, dusting, and controlled or slow release compositions in the art may be used by substituting or adding a compound of this invention to compositions known or apparent to the art.
  • the compositions may be formulated and applied with other suitable active ingredients, including other nematicides, insecticides, acaricides, fungicides, plant regulators, herbicides, fertilizers, etc.
  • an effective nematode controlling amount of active ingredient must be applied, sometimes referred to herein as a "nematicidal amount.” While the application rate will vary widely depending on the choice of compound, the formulation and mode of application, the plant species being protected and the planting density, a suitable use rate may be in the range of 0.5 to 25 kg/hectare, preferably 1 to about 20 kg/hectare.
  • the compounds of this invention are usually applied by incorporating a formulation thereof into the soil in which plants or agricultural crops are or are to be planted, i.e., the locus of infestation. This may be achieved by incorporating the compounds into the soil or by broadcasting the formulation over the planted area or the area to be planted or by limiting the application to a small area or band in the root zone where plants are or are to be planted. It will be readily apparent where the latter method is employed that a nematicidal amount, that is, a nematicidal concentration in the soil, must be applied to the root zone.
  • a suitable concentration for this purpose is in the range of 0.1 to about 50 parts by weight of compound of the invention per million parts of soil.
  • Emulsifier A 4.0%
  • Emulsifier B 0.4% Emulsifier C 0.8%
  • Emulsifier A is the anionic calcium salt of dodecylbenzene sulfonate.
  • Emulsifier B is a nonionic 6-molar ethylene oxide condensation product of nonylphenol.
  • Emulsifier C is a nonionic 30-molar ethylene oxide condensation product of nonylphenol.
  • Emulsifier D is a nonionic paste of 100% polyalkylene glycol ether.
  • Emulsifier A 4.2%
  • Emulsifier B 0.5%
  • Emulsifier D 1.4% Refined xylene solvent 71.7%
  • Emulsifier F 3.0%
  • Emulsifier G 3.0% Dormant spray oil solvent
  • Emulsifier E is an oil-soluble nonionic blend of polyoxyethylene ethers commercially available under the trademark and designation "T Mulz 808A”.
  • Emulsifier F is a formulated nonionic concentrate commercially available under the trademark and designation "FloMo 200-4”.
  • Emulsifier G is the anionic free acid of a complex organic phosphate ester commercially available under the trademark and designation "Gafac RE-410". 3. Typical granule formulations:
  • the carrier/diluent is a 20/40 or 60/90 mesh hydrated aluminum magnesium silicate of low volatile matter having 2% free moisture.
  • Biological Testing Compounds of this invention were tested as follows for nematicidal and anthelmintic activity as dust formulations (initial and residual activity) and as acetone/water formulations (systemic activity). The formulations are described above.
  • Root-Knot Nematicidal Activity The activity against root-knot nematode (Meloidogyne incognita) was determined by incorporating the compound of the invention in nematode infested soil at rates in the range of 10 ppm to 0.078 ppm of compound. Several tomato or cucumber seedlings were planted in the nematode infested soil. Two weeks after planting the test pots were evaluated to ascertain the degree of galling (swelling) on the roots of the plants, indicating the control provided by the test chemical.
  • Knot index is a numerical designation assigned at evaluation, having the following meanings:
  • Percent control is related to knot index as follows:
  • Knot Index When the Knot Index is between 0 and 1 it is further subdivided as follows to indicate how close the percent control is to 75% or 100%:
  • Residual Root-Knot Nematicidal Activity The ability of nematicidal compounds of the invention to control root-knot nematode infestations in soil over a period of time after treatment was evaluated. Dust formulations of test compound (5%) were incorporated into soil samples at test compound rates of 5 and 10 ppm. Subsequently, the treated soil samples were inoculated with nematode inoculum at weekly intervals, and Knot Index and Percent Control determined on seedlings planted in the soil samples. Specifically, soil treated with test compound was placed in 7.6 cm. diameter fiber pots and stored in a greenhouse.
  • nematicidal compounds of the invention to move through nematode-infested soil and to control the nematodes was evaluated by incorporating 5% dust formulations of test compound at 30 ppm rates into pots of root-knot nematode infested soil, and subsequently eluting the soil with 15 cm of water (equivalent to 15 cm of rainfall) into a series of two or more pots of untreated, but nematode-infested, soil.
  • the pots were 8 cm diameter plastic pots containing a 10 cm 3 layer of sand over a coarse grade filter paper disc. Sufficient soil was placed over the sand to fill the pots, and a second filter paper disc was placed over the soil.
  • Each test compound-treated pot was nested over a series of two or more pots containing untreated, but nematode- infested soil, also containing sand filter paper discs as described for the treated soil pots. Fifteen cm of water was slowly dripped into the top pots and the pots were allowed to drain for 16-18 hours to remove excess water. The top filter of each pot was then removed and the pots were planted with a cucumber or tomato seedling. The seedlings were evaluated approximately two weeks after planting to give the test results reported in Tables 7 and 7a appended. The data indicate good soil mobility and nematicide control at the application rates tested as compared to untreated systems which showed no nematode control. "Knot Index" and "Percent Control" are as defined in the initial root-knot nematode tests above. 8. Systemic Activity
  • the plants are then grown in a growth chamber at 25oC for three days and inoculated with a standard nematode culture by incorporating the inoculum into the top cm of soil in the pots.
  • the plants are returned to the growth chamber for about two weeks at which time the pots are allowed to dry until the plants begin to wilt.
  • the roots are shaken free of soil and the degree of galling (swelling) noted as compared to galling of untreated control plants.
  • the results are expressed as Knot Index and Percent Control as defined in the initial root-knot nematode activity tests reported above in Table 2. Table 8 appended reports the test results.
  • test medium consisting of 5 mg ampicillin, 10,000 units of mycostatin and 10 ml of a dense suspension of Escherichia coli per 100 ml of a buffer solution, was pipetted into each well of a 24-well microtiter plate.
  • the candidate nematicide suspended at the appropriate concentration in dimethylsulfoxide, was added to the wells in 2.5 1 volumes. Each rate of application was replicated two to three times. After thorough mixing of the contents of each well, 50 to 100 1 of a nematode suspension in a buffer was added so that each well received 10-15 nematodes. After the nematodes were added, the microtiter plates were incubated at 20°C for 5-6 days.

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Abstract

Des composés de polyhaloalcène ont la formule (I), dans laquelle X représente soufre, oxygène, azote ou méthylène, Y1 et Y2 représentent indépendamment fluor, chlore ou brome, Z représente hydrogène ou le même élément que Y1ou Y2, et n est compris entre 1 et 4; à condition que A) Lorsque X représente du soufre, R représente thiazolyl, thiényle éventuellement substitué, thianaphtyle éventuellement substitué, thiazolinyle éventuellement substitué, thiadiazolyle éventuellement substitué, oxadiazolyle éventuellement substitué ou 3,4,4- trifluoro-3- butényloxycarbonyleméthyle; B) Lorsque X représente de l'oxygène, R représente C(0)R1, où R1 est perfluoroalkyle, phényle éventuellement substitué, thiényle éventuellement substitué, furanyle éventuellement substitué, pyrolyle éventuellement substitué ou dihydrothiazolylthiométyle; C) Lorsque X est de l'azote, R associé à l'azote soit un groupe isothiocyanate, succinimide ou saccharine, et D) Lorsque X représente du méthylène, R représente un hydroxyde. Ces composés agissent contre des nématodes et des helminthes des végétaux qui indiquent une activité anthelmintique chez l'animal sont par conséquent utiles pour des applications agricoles et vétérinaires.
EP19860904515 1985-06-20 1986-06-12 Pesticidal polyhaloalkene derivatives Ceased EP0228447A4 (en)

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EP0263066A3 (fr) * 1986-09-26 1988-06-01 Ciba-Geigy Ag Dérivés de 2-mercapto-oxadiazole et -thiadiazole, procédé pour leur préparation et nématicides les contenant
EP0290379A3 (fr) * 1987-04-03 1989-02-22 Ciba-Geigy Ag 2-Mercapto-5-pyrazinyl-1,3,4-oxadiazoles et -1,3,4-thiadiazoles, procédé pour leur préparation et leur utilisation comme agents nematicides
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DK84387A (da) 1987-02-19
CN86104207A (zh) 1987-04-01
HU204022B (en) 1991-11-28
IL79143A0 (en) 1986-09-30
BR8606746A (pt) 1987-10-13
KR910000247B1 (ko) 1991-01-23
AU6122986A (en) 1987-01-13
OA08484A (fr) 1988-07-29
HUT42424A (en) 1987-07-28
WO1986007590A1 (fr) 1986-12-31
AU601656B2 (en) 1990-09-13
CA1277668C (fr) 1990-12-11
EP0228447A4 (en) 1990-12-27
MY102076A (en) 1992-03-31
DK84387D0 (da) 1987-02-19
KR870700589A (ko) 1987-12-30

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