KR900007311A - 살충제 - Google Patents
살충제 Download PDFInfo
- Publication number
- KR900007311A KR900007311A KR1019890016642A KR890016642A KR900007311A KR 900007311 A KR900007311 A KR 900007311A KR 1019890016642 A KR1019890016642 A KR 1019890016642A KR 890016642 A KR890016642 A KR 890016642A KR 900007311 A KR900007311 A KR 900007311A
- Authority
- KR
- South Korea
- Prior art keywords
- cyclopropyl
- dieneamide
- penta
- methyl
- trans
- Prior art date
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- 239000000575 pesticide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- -1 trifuoromethyl Chemical group 0.000 claims abstract 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 13
- 239000001257 hydrogen Substances 0.000 claims abstract 13
- 125000005843 halogen group Chemical group 0.000 claims abstract 12
- 125000003118 aryl group Chemical group 0.000 claims abstract 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract 8
- 239000000203 mixture Substances 0.000 claims abstract 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000004429 atom Chemical group 0.000 claims abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- 241000607479 Yersinia pestis Species 0.000 claims abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- 239000001301 oxygen Substances 0.000 claims abstract 4
- 230000000361 pesticidal effect Effects 0.000 claims abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims abstract 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims abstract 2
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 125000004276 dioxalanyl group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 17
- FDSSYPNUQHQSIQ-UHFFFAOYSA-N penta-2,4-dienamide Chemical compound NC(=O)C=CC=C FDSSYPNUQHQSIQ-UHFFFAOYSA-N 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 9
- 238000000034 method Methods 0.000 claims 7
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000005540 biological transmission Effects 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000002405 diagnostic procedure Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/247—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aromatic amines (N-C aromatic linkage)
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/10—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing rings other than six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C327/44—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
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- C—CHEMISTRY; METALLURGY
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- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
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- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/457—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing halogen
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- C07C47/546—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings polycyclic
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- C07C47/00—Compounds having —CHO groups
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C07C49/237—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
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- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
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- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
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- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/72—Polycyclic acids
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C07C2601/00—Systems containing only non-condensed rings
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- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- Insects & Arthropods (AREA)
- Biochemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Lubricants (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyamides (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
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Description
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Claims (15)
- a) 위티그(Wittia)형 반응을 통해 하기식(Ⅰ)의 잔기를 형성하거나, b) X가 산소일때, 상응하는 산 또는 하기식(B)의 산유도체를 하기식(c)의 아민과 반응시킨 뒤, 임의로 기술분야에서 잘 알려진 방법으로 식(Ⅰ)의 화할물을 식(Ⅰ)의 화합물을 식(Ⅰ)의 다른 화합물로 전환시키는 것을 포함하는 하기식(Ⅰ)의 화합물 또는 그 염의 제조방법QQ1CR2=CR3CR4=CR5C(=X)NHR1(Ⅰ)tf; 식중, Q는 모노사이클 방향족 고리 또는 하나의 원자가 질소이고 나머지 탄소 각각의 고리 시스템이 임의로 치환된 9 또는 10개의 원자를 함유하는 방향족인 적어도 하나의 고리를 지닌 융해된 비사이클 고리시스템, 또는 Q는 디할로비닐기 또는 R6가 C1-4알킬, 트리 C1-4알킬실릴, 할로겐 또는 수소이며, Q1은 C1-3알킬, 할로 C1-3할로알킬, 알키닐, 또는 시아노로 부터 선택된 하나 이상의 기에 의해 임의 치환된 1, 2-시클로프로필 고리이며, R2, R3, R4및 R5는 동일하거나 서로 다르며, 적어도 하나는 수소이고, 나머지는 수소, 할로, C1-4알킬 또는 C1-4할로알킬로 부터 각각 선택되며 X는 산소 또는 황이며, R1은 수소 및 디옥살란일, 할로, 시아노, 트리플루오로 메틸, 트리플루오로메틸티오 또는 C1-6알콕시에 의해 임의 치환된 C1-5히드로 카르빌로 부터 선택된다.CR2=CR3CR4=CR5C(=X)NHR1(A)QQ1CR2=CR3CR4=CR5C(=X)Z' (B)H2NR1(C)상기 식중, Q,Q',R2, R3,R4,R5및 R1상기에서 정의한 바와 같으며 Z1은 히트록시, C1-6알콕시, 할로 또는 포스포로 이미데이트 에스테트(-P(0) (0-아릴)NH-아릴(여기서, 아릴은 C6-10=0아릴임이며, X는 산소이다.
- 제1항에 있어서, Q가, 내지 3개의 할로 또는 할로, 시아노 또는 너트로에 의해 각각 임의 치환된 C1-6히드로카르빌 C1-6알콕시 또는 메틸렌디옥시로 부터 선택된, 1내지 4개의 기에 의해 각각 임의 치환된 페닐, 피리닐, 티에닐 또는 나프틸기, 또는 치환체가 n=0, 1 또는 2이고, R7이 하나 또는 두개의 C1-6알킬 또는 R7이 하나 이상의 할토에 임의 치환된 C1-6알킬기에 의해 임의 치환된 아미노인 S(O)7NR7기 또는 회전체가 및 R8및 R9가 각각 수소, C1-6알킬로 부터 선택된 NR8R9기 또는 R10이 C1-6알킬인 COR10기인 것을 특징으로 하는(Ⅰ)의 화합물의 제조방법.
- 제1항 또는 제2항에 있어서, R2, R3,R4및 R5가 수소, 메틸 또는 플루오로로 부터 선택되는 것을 특징으로 하는 식(Ⅰ)의 화합물의 제조방법.
- 제1항 내지 제3항중 어느 한항에 있어서, 시클로프로필 고리 Q1은 비치환되고2-위치는 플루오로 또는 클로로에 의해 치환 또는 비치환 되는 것을 특징으로 하는 식(I)의 화합물의 제조방법.
- 제1항 내지 제4항중 어느 한항에 있어서, R1이소부틸, 1, 2-디메틸프로필, 1,1,2-트리메틸프로필, 2,2-디메틸프로필, 2-메틸프로프-2-에닐 또는 (2-메틸-1, 3-디옥산-2-일)메틸인 것을 특징으로 하는 식(I)의 화합물의 제조방법
- 하기식(Ⅱ) 또는 그 염의 제조방법.QaQ1aCR2a=CR3aCR4aCR5aC(=Xa)NHR1a(Ⅱ)상기식에서 Qa는 임의로 치환된 페닐 또는 페닐기, 또는 하나의 원자가 질소이고, 나머지가 탄소인 9 또는 10개의 원자를 함유하는 방향족인 적어도 하나의 고리를 지닌 융해된 비사이클 고리 시스템, 또는 Qa는 디할로비닐기 또는 R6a가 C1-4알킬, 트리알킬실릴 또는 수소인 R6a-C=C-기이며, Q19는 C1-3알킬, 할로 또는 X1-3할로알킬로 부터 선택된 하나이상의 기로 임의 치환된 1,2-시클로필로필 고리이며, R2a, R3a, R4a및 R5a는 동일하거나 사로 다르며, 적어도 하나는 수소이고, 나머지는 수소, 할로 C1-4알킬 또는 C1-4할로알킬로 부터 각각 선택되며, R1a는 소수 및 디옥살란일, 할로, 시아노, 트리플루오로 메틸, 트리플루오로메틸티오 는C1-6알콕시에 의해 임의 치완된 C1-6히드로카르빌로 부터 선택된다.
- (±)-(2E,43) N-이소부틸-3-메틸-5-메틸-5-[트랜스-2-(4-클로로 페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-(2-메틸프로프-2-에닐)-3-메틸-5-[트랜스-2-(3,4-디브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-[트랜스-2-(3-트리플루오로메틸-4-클로로페닐)시클로프로필] 펜타-2-4디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-[트랜스-2-(3.5-디클로로-4-브로모페닐) 시클로프로필] 펜타-2,4-디엔아미드, ±)-(2E,4E) N-이소부틸-3-메틸-5-[트랜스-8-(3,4,5-트리클로로-페닐) 시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-4-플루오로-5-[트랜스-2-(3,4-디클로페닐) 시클로프로필] 펜타2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)5-[트랜스-2-(3-클로로-4-브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-[트랜스-2-(3-클로로-4-브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-5-[트랜스-2-(4-브로모페닐)-시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-(트랜스-2-(3,5-비스트리 플루오로메틸-페닐)시클로프로필)-2,4-디엔아미드, (±)-(2E,4E) N-(1-2-디메틸프로필)-5-(트랜스-2-(3,5-비스트리 플루오로메틸프로필)시클로프로필)-2,4-디엔아미드, (±)-(2E,4E) N-(1-2-디메틸프로필)-5-(트랜스-2-(3,4-디클로로페닐)시클로프로필)-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-(트랜스-2-(3,4-디클로로페닐시클로프로필)-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-5(트랜스-2-(4-클로로페닐)시클로프로필)-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-5-[트랜스-2-(3,4-디블로모-페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-[트랜드-2-(3,4-디브로모-페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-5-[트랜스-2-(3-브로모-4-클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-[r-1-플루오프-c-2-(3,4,5-트리클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-[r-1-플루오로-c-2-(3,4,5-트리클로로페닐)시클로프로필]펜타-2,4-3-디엔아미드, (±)-(2Z,4E) N-이소부틸-2-플루오로-3-메틸-5-[트랜스-2-(3,4-디클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2Z,4E) N-(2-메틸프로필-2-에닐)-2-에닐)-2-플루오로-3-메틸-5-(트랜스-2-(3,4-디클로로페닐)시클로프로필 펜타-2,4-디엔아미드, (±)-(2E,4E) N-(S-부틸)-5-[트랜스-2-(3,4-디클로로페닐)시클로프로필 펜타-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-5-[r-1-플로오로-c-2-(3,4-디클로로페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(2-메틸프로프-2-에닐)-3-[r-1-플로오로-c-2-(3,4-디브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-이소부틸-3-메틸-5-메틸-5-[r-1-플로오로-c-2-(3,4-디브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(1,2-디메틸프로필)-5-[r-1-플로오로-c-2-(3,4-디브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-이소부틸-3-메틸-5-[r-1-플루오로-c-2-(3,4-디클로로페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(1,2-디메틸프로필)-5-[r-1-클로로-c-2-(3,4-디클로로페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(2-메틸프로로프-2-에닐)-3-메틸-4-플루오로-5-트랜스-2-(3,4-디클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-이소부틸-3-3메틸-[r-1-클로로-2-c-(3,4-디클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(2-메틸프로프-2-에닐)-3-메틸-[r-1-플루오로-2-c-(3,4-디클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(2-메닐프로프-2-에닐)-3-메틸-5-[r-1-플루오로-2-c-(3,4-5트리클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E,4E) N-(2-메닐프로프-2-에닐)-3-메틸-5-[트랜스-2-(3,4-디브로모페닐)시클로프로필]펜타-2,4-디엔아미드로 부터 선택되는 화합물의 제조 방법.
- 제1항에 있어서, 상기(a)방법이 알데히드기 또는 케톤기를아미드/티오 아미드 말단부 또는 식(I)의 QQ1분절에 부착시키고 이어서 이것을 적당한 포스포러스 일리드와 반응시키는 것을 포함하는 방법.
- 제9항에 있어서, QQ1(CR2-CR3)COR4를 Z2CHR5(C=X)NHR1과 반응시키거나, QQ1COR2를 Z2CHR3CR4=(C=X)NHR1과 반응시키거나, 또는 QQ1(CR2=CR3)CHR4Z2를 R5CO=(C=X)NHR1과 반응시키거나, 또는 QQ1(CR2=CR3)CHR4Z2를 방법.[상기식중, Q,Q1,X 및 R1내지 R5는 상기 식(I)에서 정의한 바와같이며, Z2는 (아릴)3P, (아릴)P(O) 또는 (C1-4알콕시)2PC(O)이다.
- 식 QQ1CR2=CR3CR4=CR5(=X)Z1, QQ1(CR2=CR3)COR4QQ1COR2또는 QQ1(CR2-CR3)CR4Z2의 신규 화학중간체.
- 제1항 내지 제8항중의 어느 한항에 기술된 식(I)의 화합물의 혼합도니 담체 또는 희석제를 포함하는 살충 또는 진드기 구제 조성물.
- 식(I)의 화합물 및 담체 또는 희석제의 상승 작용을 위해 제1항 내지 제8항중 어느 한항에 기술된 식(I)의 화합물을 포함하는 상승 작용된 살충 조성물.
- 제1항 내지 제8항중의 어느 한항에 기술된 식(I)의 화합물과 다른 살충 화합물의 혼합물.
- 제1항 내지 제8항중의 어느 한항에 기재된 화합물 또는 제11항 내지 제13항중의 어느 한항에 기재된 조성물 또는 혼합물을 해충 또는 해충 전염에 민감한 환경에 적용되는 것을 포함하는 해충의 구제 방법.
- 인체 또는 동물에서 행하는 외과 수술 또는 치료 방법, 또는 인체 또는 동물에서 행하는 진단 방법에 유용한 제1항 내지 제8항중의 어느 한항에 기재된 화합물 또는 제11항 내지 제13항중의 어느 한항에 기재된 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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DE (1) | DE68911876T2 (ko) |
DK (1) | DK571489A (ko) |
ES (1) | ES2062036T3 (ko) |
FI (1) | FI895433A0 (ko) |
GB (1) | GB8826760D0 (ko) |
HU (2) | HU9300081D0 (ko) |
IE (1) | IE64377B1 (ko) |
IL (1) | IL92317A (ko) |
MC (1) | MC2070A1 (ko) |
OA (1) | OA09145A (ko) |
PL (3) | PL162284B1 (ko) |
PT (1) | PT92323B (ko) |
RU (3) | RU2010025C1 (ko) |
SK (1) | SK646189A3 (ko) |
TR (1) | TR25218A (ko) |
ZA (1) | ZA898725B (ko) |
ZW (1) | ZW15189A1 (ko) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9113624D0 (en) * | 1991-06-25 | 1991-08-14 | Wellcome Found | Pesticides |
GB9126955D0 (en) * | 1991-12-19 | 1992-02-19 | Wellcome Found | Pesticides |
EP0549418A3 (en) * | 1991-12-23 | 1993-10-20 | Roussel Uclaf | Unsaturated amides with pesticidal activity |
FR2729945B1 (fr) * | 1995-01-26 | 1997-04-25 | Hoechst Schering Agrevo Sa | Nouveaux amides aromatiques, leur procede de preparation, les compostions les contenant et leur utilisation comme pesticides |
US6403638B1 (en) | 1998-10-01 | 2002-06-11 | Allergan Sales, Inc. | 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
US6147224A (en) * | 1998-10-01 | 2000-11-14 | Allergan Sales, Inc. | 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
DE10018370A1 (de) | 2000-04-14 | 2001-10-18 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4855086A (en) * | 1982-10-15 | 1989-08-08 | Burroughs Wellcome Co. | Novel pesticides, preparation and use |
GB8504097D0 (en) * | 1985-02-18 | 1985-03-20 | Wellcome Found | Pesticidal compounds |
ZW3686A1 (en) * | 1985-02-18 | 1987-09-23 | Wellcome Found | Pesticidal compounds |
-
1988
- 1988-11-16 GB GB888826760A patent/GB8826760D0/en active Pending
-
1989
- 1989-11-15 MC MC892076A patent/MC2070A1/xx unknown
- 1989-11-15 PT PT92323A patent/PT92323B/pt not_active IP Right Cessation
- 1989-11-15 CN CN93117309A patent/CN1091423A/zh active Pending
- 1989-11-15 IL IL9231789A patent/IL92317A/en not_active IP Right Cessation
- 1989-11-15 ZA ZA898725A patent/ZA898725B/xx unknown
- 1989-11-15 CN CN89109195A patent/CN1027692C/zh not_active Expired - Fee Related
- 1989-11-15 PL PL89284065A patent/PL162284B1/pl unknown
- 1989-11-15 HU HU9300081A patent/HU9300081D0/hu unknown
- 1989-11-15 IE IE365789A patent/IE64377B1/en not_active IP Right Cessation
- 1989-11-15 AT AT89311815T patent/ATE99286T1/de active
- 1989-11-15 TR TR89/0964A patent/TR25218A/xx unknown
- 1989-11-15 CA CA002003052A patent/CA2003052A1/en not_active Abandoned
- 1989-11-15 PL PL89282310A patent/PL163550B1/pl unknown
- 1989-11-15 FI FI895433A patent/FI895433A0/fi not_active IP Right Cessation
- 1989-11-15 CZ CS896461A patent/CZ646189A3/cs unknown
- 1989-11-15 KR KR1019890016642A patent/KR0140890B1/ko not_active IP Right Cessation
- 1989-11-15 DK DK571489A patent/DK571489A/da not_active Application Discontinuation
- 1989-11-15 OA OA59682A patent/OA09145A/xx unknown
- 1989-11-15 HU HU895912A patent/HU209286B/hu unknown
- 1989-11-15 PL PL89297791A patent/PL163669B1/pl unknown
- 1989-11-15 RU SU894742606A patent/RU2010025C1/ru active
- 1989-11-15 AU AU44716/89A patent/AU630123B2/en not_active Ceased
- 1989-11-15 EP EP89311815A patent/EP0369762B1/en not_active Expired - Lifetime
- 1989-11-15 ZW ZW151/89A patent/ZW15189A1/xx unknown
- 1989-11-15 ES ES89311815T patent/ES2062036T3/es not_active Expired - Lifetime
- 1989-11-15 DD DD89334602A patent/DD298926A5/de not_active IP Right Cessation
- 1989-11-15 SK SK6461-89A patent/SK646189A3/sk unknown
- 1989-11-15 DE DE89311815T patent/DE68911876T2/de not_active Expired - Fee Related
- 1989-11-15 JP JP1297232A patent/JP2667916B2/ja not_active Expired - Lifetime
- 1989-11-16 BR BR898905808A patent/BR8905808A/pt not_active IP Right Cessation
-
1990
- 1990-05-15 RU SU904743786A patent/RU2055476C1/ru active
-
1992
- 1992-09-16 RU SU925052551A patent/RU2072351C1/ru active
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