CN1101040A - 二芳基衍生物及其作为作物保护剂的应用 - Google Patents
二芳基衍生物及其作为作物保护剂的应用 Download PDFInfo
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- CN1101040A CN1101040A CN94105153A CN94105153A CN1101040A CN 1101040 A CN1101040 A CN 1101040A CN 94105153 A CN94105153 A CN 94105153A CN 94105153 A CN94105153 A CN 94105153A CN 1101040 A CN1101040 A CN 1101040A
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- 238000010413 gardening Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
- QJPWUUJVYOJNMH-UHFFFAOYSA-N homoserine lactone Chemical compound NC1CCOC1=O QJPWUUJVYOJNMH-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical class CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- WJZHMLNIAZSFDO-UHFFFAOYSA-N manganese zinc Chemical compound [Mn].[Zn] WJZHMLNIAZSFDO-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SPUACDWLOLSOQO-UHFFFAOYSA-M methoxyazanium;chloride Chemical compound [Cl-].CO[NH3+] SPUACDWLOLSOQO-UHFFFAOYSA-M 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- ACUBUDUYSFODKZ-UHFFFAOYSA-N methyl n-(phenylcarbamothioyl)carbamate Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1 ACUBUDUYSFODKZ-UHFFFAOYSA-N 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical compound NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000009700 powder processing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ZSWXYQDKHXCYPG-UHFFFAOYSA-N triethyl(1,3-thiazol-2-yl)stannane Chemical compound CC[Sn](CC)(CC)C1=NC=CS1 ZSWXYQDKHXCYPG-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- 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
- C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
-
- 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
- A01N43/14—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 six-membered rings
- A01N43/18—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 six-membered rings with sulfur as the ring hetero 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
- 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
- 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
- A01N43/80—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
-
- 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
- A01N43/82—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 three ring hetero atoms
-
- 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
- C07D261/08—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- 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
-
- 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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pyrrole Compounds (AREA)
Abstract
通式I二芳基衍生物及包含该化合物的杀真菌
剂,通式I如下,其中A是=CHOR’,=CHSR’,=CHR’,=CHCl或=NOR’,B是OR2,SR2或NR2R3且Het是未取代的或被R取代的单环、双环或三环的芳族5元或6元杂环结构;R1-R5相同或不同,各自是氢或烷基;U,V,W相同或不同各自是卤素、烷基或烷氧基。
Description
本发明涉及通式Ⅰ的新的二芳基衍生物
式中
A是=CHOR′,=CHSR′,=CHR′,=CHCl或=NOR′,
B是OR2,SR2或NR2R3,
Het是可带有1-3个R基团的单环、双环或三环的5元或6元杂环结构。
R是卤素、硝基、氰基、CO2R4、NR4R5、CONR4R5、S(O)nR4P(O)(OR4)2、取代或未取代的C1-6烷基、C1-4卤代烷基、取代或未取代的C3-6环烷基、C1-4烷氧基C1-4烷基、C1-4烷硫基C1-4烷基、取代或未取代的C2-6链烯基、取代或未取代的C2-6炔基、C1-6烷氧基、C1-4硫代烷氧基、取代或未取代的苄硫基、C1-4烷基羰基、取代或未取代的苯基羰基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的芳硫基、取代或未取代的芳基C1-4烷基、取代或未取代的芳基C2-4链烯基、取代或未取代的芳基C2-4炔基、取代或未取代的芳氧基C1-4烷基、取代或未取代的芳硫基C1-4烷基、取代或未取代的杂芳基、取代或未取代的杂芳氧基、取代或未取代的杂芳基C1-4烷基、取代或未取代的杂芳基C2-4链烯基、取代或未取代的杂芳氧基C1-4烷基,
“取代或未取代的”所指的取代基是卤素、氰基、硝基、C1-4烷基、C1-4烷氧基、C1-4卤代烷基、C1-4卤代烷氧基或C1-4烷氧基亚氨基C1-2烷基,其中
n是0,1或2。
R1,R2,R3,R4,R5相同或不同,各自是氢或C1-4烷基,
U,V,W相同或不同,各自是卤素、C1-4烷基或C1-4烷氧基。
本发明还涉及用这些化合物抗害虫,尤其是真菌,线虫和螨的方法。
2-苯基-3-甲氧基丙烯酸苯酯或苯基乙醛酸甲酯-0-甲肟的苯基上的2位被杂芳甲基、杂芳乙基、杂芳氧基、苯基或杂芳氧基甲基取代时可用作杂真菌剂这一事实已经公开(EP-A178826,EP-A350691,EP-A363818,EP-A378755和EP-A254426)。但其杀真菌作用并不令人满意。
本发明的目的是提供性能更好的新化合物。
我们发现该目的可通过新化合物Ⅰ达到。我们还发现,化合物Ⅰ具有极好的杀真菌、杀昆虫、杀线虫、和杀螨作用。其杀真菌和杀昆虫作用特别好。
通式Ⅰ化合物的制备描述如下:
基团
通式Ⅰb的新化合物可用例如下述方法制备:按常规方法,将通式1的溴代芳族化合物与杂芳族锡化合物2或杂芳族硼化合物3反应,反应在过渡金属催化剂(TM)、最好在诸如NiCl2,Pd(OAc)2,PdCl2或Pd(PPh3)4之类的镍或钯化合物存在下进行(参见:例如Synthesis,693(1987),T.R.Bailey,Tetrah.Lett.4407(1986);Y.Yamamoto,Hetercycles 16,1161(1981))。杂芳族锡和硼化合物是已知的或者可按类似于已知方法制备的。
路线1
通式Ⅰ化合物的另一种制备方法是[3+2]-偶极环化加成,Het代表芳香5元杂环结构。
这样,乙炔衍生物4可以按常规方式与1,3-偶极5反应得到所需的芳香5元杂环结构6(参见Houben-Weyl,vol 5/2a,pp.830 et seq.(1977))。
路线2
例如这样可制得下列衍生物:
-与氧代氰7反应可制得异噁唑衍生物8和9。
路线3
-也可以在高氯酸盐存在下将通式10肟与乙炔11反应,得到异噁唑12和13。
路线4
-将乙炔4与叠氮化物14反应可制得通式15三唑。
路线5
-与重氮基烷16反应可制得吡咯17和18。
路线6
噁唑衍生物22可以例如从酰脘21制得,而酰脘21可通过醛19与酰肼20反应制得(参见EP499823)。
路线7
-脘21氧化变成噁二唑22的过程例如可在溶剂或稀释剂如二氯甲烷或稀释剂如二氯甲烷或氯仿中用四乙酸铅或溴进行(参见例如Synthesis,411,1986)。
还有一种可能的制备式Ⅰ新化合物的方法如路线8所示:
路线8
-醛可按常规方式经过氰醇26转变为扁桃酸衍生物29(参见例如US-A2892847),它又可按类似于已知的方法氧化成酮酯30,例如用次氯酸钠氧化(参见例如EP-A140454)。
-从卤代衍生物24经过Grignard或金属有机中间体阶段也可一步制得酮酯30(参见例如Synth.Comm.20,1781(1990))。
-还有一种可能的制备酮酯的方法是将酰氯25转变为苯甲酰腈28,然后用Pinner反应将它转变为酮酯30(参见例如EP-A493711)。
由上面制得的酮酯30可按下述方法制得通式Ⅰ的酯:
路线9
a)用甲氧基氨基盐酸化物将酮酯23转变成肟醚Ⅰc,或者
路线10
b)通过Witting反应或Witting-Horner反应,使酮酯23与内鎓盐31反应。
按如下的常规方式从酯Ⅰe可制得硫醇酯或甲酰胺:
路线11
用常规方式经过中间体化合物酸32和酰氯33可制得硫醇酯Ⅰg(参见EP-A432503)。
甲酰胺Ⅰf可直接通过酯Ⅰe的氨解(参见EP-A477631)或通过酰氯33的氨解(EP-A477631)制得。
由于存在C=C或C=N双键,通式Ⅰ新化合物可以E/Z异构体混合物的形式得到,这些异构体可按常规方式分离得到单独成份。例如用结晶法或色谱法分离。单独的异构体化合物及其混合物都包括在本发明范围内,并且可用作杀虫剂。
通式Ⅰ中的基团具有例如如下意义:
A是=CHOR′,=CHSR′,=CHR′,=CHCl或=NOR′,
B是OR2,SR2或NR2R3,
Het 是单环,双环或三环的芳族5元或6元杂环,例如吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、四嗪基、喹啉基、吩嗪基、噻吩基、吡咯基、咪唑基、噁唑基、异噁唑基、噻唑基、噻二唑基、噁二唑基、四唑基、苯并噻吩基、苯并呋喃基、吲哚基、苯并咪唑基、苯并恶唑基、苯并噻唑基或苯并异恶唑基,它们也可以是被1-3个基团R取代的,其中
R 可相同或不同,是氢、卤素(例如氟、氯、溴、碘)、硝基、氰基、NR4R5、CO2R4,CONR4R5,S(O)nR4(其中n=0,1或2)、P(O)(OR4)2、直链或支链C1-10烷基(例如甲基、乙基、正丙基和异丙基,正丁基、异丁基、仲丁基和叔丁基,正戊基、新戊基、正已基、正癸基)、C1-4卤代烷基(例如氯甲基、溴甲基、氟甲基、二氯甲基、二氟甲基、三氟甲基、1,2-二溴甲基、1,1,2,2-四氟乙基、五氟乙基)、C3-6环烷基(例如环丙基、1-甲基环丙基、环丁基、环戊基、环已基)、C1-4烷氧基C1-4烷基(例如甲氧基甲基、乙氧基甲基、叔丁氧基甲基、甲氧基乙基、乙氧基乙基、丁氧基乙基)、C1-4烷硫基C1-4烷基(例如甲硫基甲基、甲硫基乙基)、C2-6链烯基(例如乙烯基、丙烯-1-基、丙烯-2-基、丙烯-3-基、2-丁烯-2-基)、取代或未取代的C2-6炔基(例如:乙炔基、甲氧基乙炔基、丙炔基、3-苯基乙炔-1-基、3-羟基丙炔-1-基;3-氯丙炔-1-基)、C1-6烷氧基(例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基),C1-4烷硫基(例如甲硫基)、取代或未取代的苄硫基(例如2-氯苄硫基)、C1-4烷基羰基(例如乙酰基、丙酰基、异丁酰基)、取代或未取代的苯基羰基(例如2-氯苯基羰基、4-甲基苯基羰基)、取代或未取代的芳基、苯基、萘基(例如4-甲基苯基、3-羟基-4-甲基苯基、1-萘基、2-甲基-1-萘基)、取代或未取代的芳氧基(例如苯氧基、2-甲基苯氧基、4-氯苯氧基、3-硝基苯氧基)、取代或未取代的芳硫基(例如苯硫基)、取代或未取代的芳基C1-4烷基(例如苄基、2-氯苄基、2,5-二甲氧基苄基、苯乙基、4-甲基苯乙基)、取代或未取代的芳基C-链烯基(苯乙烯基、2-氯苯乙烯基)、取代或未取代的芳基C2-4炔基(例如苯乙炔基、4-甲基苯乙炔基、2-萘基乙炔基)、取代或未取代的芳氧基C1-4烷基(例如苯氧基甲基、2-氰基苯氧基甲基、1-萘氧基甲基、苯氧基乙基)、取代或未取代的芳硫基C1-4烷基(例如苯硫基甲基)、取代或未取代的杂芳基(例如吡啶基、噻吩基、2-氯噻吩-5-基)、取代或未取代的杂芳氧基(例如2-吡啶基氧基、2-苯并噻吩基氧基、2-苯并恶唑基氧基)、取代或未取代的杂芳基C1-4烷基(例如,4-吡啶基甲基、4-氯-2-噻吩基甲基)、取代或未取代的杂芳基C2-4链烯基(例如2-吡啶基乙烯基、6-氯-2-吡啶基乙烯基、2-噻唑基乙烯基)、取代或未取代的杂芳氧基C1-4烷基(例如吡啶氧基甲基、2-苯并恶唑氧基甲基、6-甲氧基-2-苯并噻唑氧基甲基),其中“取代或未取代的”是指取代基卤素、氰基、硝基、C1-4烷基(例如甲基、乙基)、C1-4烷氧基(例如甲氧基、乙氧基、叔丁氧基)、C1-4卤代烷基(例如三氟甲基)、C1-4卤代烷氧基(例如三氟甲氧基)、C-烷氧基亚氨基C1-2烷基(例如甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基),“杂芳基”一词定义同上;且
R1、R2、R3、R4、R5相同或不同,各自是氢或C1-4烷基(例如甲基、乙基、正丙基或异丙基、或正丁基、异丁基、仲丁基或叔丁基),且
U、V、W相同或不同,各自是氢、卤素、C1-4烷基(例如甲基、乙基、丙基、丁基)或C1-4烷氧基(例如甲氧基、乙氧基)。
优选的式Ⅰ化合物是其中A是=CHOCH3或=NOCH3的化合物。
B是甲氧基或甲氨基的化合物Ⅰ也是优选的。
U,V和W同时是氢的式Ⅰ化合物也是优选的。
而且,Het是选自下列基团的未代或未取代的杂环结构的式Ⅰ化合物是优选的:噻唑基、苯噻唑基、异噁唑基、噻二唑基、噁三唑基和噻吩基,
特别优选的式Ⅰ化合物是那些Het是选自下列基团的取代或未取代的杂环结构的化合物:噻唑-2-,苯并噻唑-2-基、异噁唑-3-基、1,3,4-噻二唑-2-基,1,3,4-噁二唑-2-基和噻吩-2-基。
Het的优选的取代基是:
C1-4烷基,它可部分或完全取代(即,其氢原子可部分或完全被选自氟、氯和/或溴的卤原子取代),和/或它可带有下列基团之一:羟基、C1-4烷氧基、C1-4烷基羰基氧基、C1-4烷基羰基氧基、苯基、萘基、苯氧基、萘氧基、苯甲酰氧基、萘甲酰氧基或噻吩基,而上述芳香基团又可带有1-3个下列基团:氰基、硝基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、C1-4卤代烷氧基和C1-4烷硫基;
C3-8环烷基,它可部分卤代和/或带有1-3个下列基团:C1-4烷基、C1-4卤代烷基、C1-4烷氧基和C1-4卤代烷氧基,
C2-6烷氧基,它可部分或完全卤代(即,其氢原子可部分或完全被选自氟、氯和/或溴的卤原子取代),和/或它可带有下列基团之一:苯基、萘基、苯氧基、萘氧基、苯甲酰氧基、萘甲酰氧基或噻吩基,而上述芳香基团又可部分或完全卤代和/或带有1-3个下列基团:氰基、硝基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、C1-4卤代烷氧基和C1-4烷硫基;
苯基、咪唑基、噻吩基、苯并噻吩基和吡啶基,这些基团本身又可部分或完全卤代和/或带有1-3个下列基团:氰基、硝基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、C1-4卤代烷氧基和C1-4烷硫基。
优选的化合物是取代基如下定义的化合物:
A是=CHOCH3或=NOCH3
B是OCH3或NHCH3
U,V,W是氢,并且
Het,R和R4,R5具有上文给出的意义
式Ⅰ新化合物适合作杀真菌剂。
新化合物或含它们的药剂可以例如以下述形式通过喷雾、雾化、喷粉、撒插或浇水来施用:可直接喷雾的溶液、粉末、悬浮液(包括高百分率水、油或其它的悬浮液)、分散体、乳液、油分散体、糊剂、喷粉剂、撒播剂或颗粒剂。施用形式完全取决于使用药剂的目的,但必须确保本发明活性成分尽可能分布均匀。
通常,用所述活性成分对植物进行喷雾或喷干粉处理,或者用活性成分处理植物的种子。
按已知方法来生产制剂,例如将活性成分掺入溶剂和/或载体中,可用或不用乳化剂和分散剂;若用水作溶剂,也可以使用其它有机溶剂作助溶剂。适于此目的助剂是溶剂,例如芳族化合物(例如二甲苯),氯代芳族化合物(例如氯代苯类),石蜡(例如粗油馏分),醇类(例如甲醇、丁醇),酮类(例如环已酮),胺类(例如乙醇胺、二甲基甲酰胺)和水;载体,例如磨细的天然矿物质(例如高岭土、氧化铝、滑石粉和白垩)和磨细的人造矿石(例如高度分散的二氧化硅和硅酸盐);乳化剂,例如非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐);和分散剂,例如木素-亚硫酸盐废液和甲基纤维素。
表面活性剂的例子有芳族磺酸的碱金属、碱土金属和铵盐,例如木素磺酸、苯酚磺酸、萘磺酸、二丁基萘磺酸和脂肪酸的碱金属、碱土金属和铵盐,烷基和烷基芳基磺酸盐,烷基、十二烷基醚和脂肪醇硫酸酯,硫酸化十六烷醇、十七烷醇和十八烷醇的盐,脂肪醇乙二醇醚的盐,磺化萘和萘衍生物与甲醛的缩合产物,萘或萘磺酸与苯酚和甲醛的缩合产物,聚氧乙烯辛基苯酚醚类,乙氧基化异辛基苯酚、乙氧基化辛基苯酚和乙氧基化壬基苯酚,烷基苯酚聚乙二醇醚,三丁基苯基聚乙二醇醚,烷基芳基聚醚醇类,异三癸基醇,脂肪醇环氧乙烷缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,十二烷醇聚乙二醇醚缩醛,山梨醇酯,木素-亚硫酸盐废液和甲基纤维素。
可以通过将活性成分与固体载体混合或一同研磨来制备粉末、喷粉剂和撒播剂。
颗粒剂,例如包衣、浸制的或均相的颗粒剂可以通过将活性成分粘合在固体载体上来制备。固体载体的例子有矿土,例如硅酸、硅胶、硅酸盐、滑石粉、高岭土、美国活性白土、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的塑料,肥料,例如硫酸铵、磷酸铵、硝酸铵和尿素,和植物产品,如谷物粉、树皮粉、木材粉、坚果壳粉、纤维素粉等。
制剂举例如下:
Ⅰ.90重量重量份本发明化合物和10重量份N-甲基-d-吡咯烷酮的溶液,适于以极细滴的形式施用。
Ⅱ.20重量份本发明化合物、80重量份二甲苯、10重量份8至10mol环氧乙烷和1mol油酸-N-一乙醇酰胺(oleic acid-N-monoethanolamide)的加合物,5重量份十二烷基苯磺酸的钙盐和5重量份40mol环氧乙烷和1mol蓖麻油的加合物的混合物。通过将该溶液细致地分散在水中而获得分散体。
Ⅲ.20重量份本发明化合物、40重量份环已酮、30重量份异丁醇、20重量份40mol环氧乙烷和1mol蓖麻油的加合物的水性分散体。
Ⅳ.20重量份本发明化合物、25重量份环已醇、65重量份沸点在210-280℃之间的矿物油馏分和10重量份40mol环氧乙烷和1mol蓖麻油的加合物的水性分散性。
Ⅴ.80重量份本发明化合物、3重量份二异丁基萘-2-磺酸的钠盐、10重量份得自亚硫酸盐废液的木素磺酸的钠盐和7重量份硅胶粉的锺磨混合物。通过将该混合物细分散在水中,制得喷雾液剂。
Ⅵ.3重量份本发明化合物和97重量份高岭土颗粒的紧密混合物。该喷粉剂含3重量%的活性成分。
Ⅶ.30重量份本发明化合物、92重量份硅胶粉和8重量份喷啉在所述硅胶表面的石蜡油的紧密混合物。活性性成分的这种制剂显示良好的粘附性。
Ⅷ.40重量份本发明化合物、10重量份苯酚磺酸-脲-甲醛缩合物的钠盐、2重量份硅胶和48重量份水的稳定的水性分散体。该分散体可进一步稀释。
Ⅸ.20重量份本发明化合物、2重量份十二烷基苯磺酸的钙盐、8重量份脂肪酸聚乙二醇醚、20重量份苯酚磺酸-脲-甲醛缩合物的钠盐和68重量份石蜡矿物油的稳定的油性分散体。
这些新化合物对广谱的植物病原性真菌极为有效,特别是对子囊菌纲和担子菌纲的真菌极有效。其中一些具有系统作用,可用作叶和土壤的杀真菌剂。
这些化合物对于防治下列植物中大量的真菌特别有用:各种作物或其种子尤其是小麦、黑麦、大麦、燕麦、水稻、玉米、草坪、棉花、大豆、咖啡、蔗糖、园艺及葡萄园中的水果和观赏植物,和蔬菜如黄瓜、豆类及南瓜。
这些化合物按下述方法来应用:用杀真菌有效量的活性成分处理种子、植物、材料或土壤以防止真菌侵害。
这些化合物可以在材料、植物或种子被真菌感染前或感染后施用。
这些新化合物尤其可用于防治下列植物疾病:
谷类中的禾白粉菌,
南瓜中的二孢白粉菌和单丝壳,
苹果中的白叉丝单囊壳,
葡萄藤中的葡萄钩丝壳,
谷类中的柄锈菌,
棉花中的立枯丝核菌,
谷类和蔗糖中的黑粉菌,
苹果中的苹果黑星菌(疮痂病),
谷类中的长蠕孢,
小麦中的颖枯壳针孢,
草莓和葡萄中的灰葡萄孢(灰霉),
花衙的落花生尾孢,
小麦和大麦中的Pseudocercosporella herpotrichoides,
水稻中的Pyricularia oryzae,
马铃薯和西红柿中的致病疫霉,
各种植物中的镰孢和轮枝孢,
葡萄中的葡萄生单轴霉,
水果和蔬菜中的链格孢。
新组合物也可以用于保护材料(树木)免受例如拟青霉侵素。
杀真菌剂通常含0.1至95重量%、优选0.5至90重量%的活性成分。
施用率取决于所需效应的种类,但一般为每公倾0.02-3kg活性成分组合物。
当用该组合物处理种子时,一般需要每公斤种子0.001-50g,优选0.01至10g的施用率。
在这些施用形式中,按照本发明的药剂也可与其它活性成分如除莠剂、杀虫剂、生长调节剂和其它杀真菌剂合用,而且可与肥料混合并一同施用。与其它杀真菌剂混合使用常常能产生更广泛的杀真菌作用。
下列的可与这些新化合物合用的杀真菌剂意在举例说明可能的配合,但对本发明范围无任何限定。
可与新化合物合用的杀真菌剂的例子有:
硫,
二硫代氨基甲酸盐类及其衍生物,例如
二甲基二硫代氨基甲酸铁,
二甲基二硫代氨基甲酸锌,
亚乙基双二硫代氨基甲酸锌,
亚乙基双二硫代氨基甲酸锰,
乙二胺双二硫代氨基甲酸锌锰,
二硫代四甲基秋兰姆,
N,N′-亚乙基双二硫代氨基甲酸锌的氨复合物;
N,N′-亚丙基双二硫代氨基甲酸锌的氨复合物;
N,N′-亚丙基双二硫代氨基甲酸锌和
N,N′-聚丙烯双(硫代氨基甲酰基)二硫化物;
硝基衍生物,例如
巴豆酸二硝基(1-甲基庚基)苯酯,3,3-二甲基丙烯酸2-仲丁基-4,6-二硝基苯酯,异丙基碳酸2-仲丁基-4,6-二硝基苯酯和5-硝基间苯二甲酸二异丙酯;
杂环物质,例如
2-十七烷基咪唑-2-基乙酸盐,
2,4-二氯-6-(邻氯苯胺基)-S-三嗪,
苯二甲酰亚氨基硫代膦酸0,0-二乙酯,
5-氨基-1-[双(二甲氨基)氧膦基]-3-苯基-1,2,4-三唑,
2,3-二氰基-1,4-二硫代蒽棍,
2-硫代-1,3-二硫代[4,5-b]喹喔啉,
1-(丁基氨基甲酰)-2-苯并咪唑氨基甲酸甲酯,
2-甲氧基羰基氨基苯并咪唑,
2-(呋喃-2-基)苯并咪唑,
2-(噻唑-4-基)苯并咪唑,
N-(1,1,2,2-四氯乙硫基)四氢苯邻二甲酰亚胺,
N-三氯甲硫基四氢苯邻二甲酰亚胺,
N-三氯氟甲硫基苯邻二甲酰亚胺,
N-二氯氟甲硫基-N′,N′-二甲基-N-苯基硫酸二酰胺,
5-乙氧基-3-三氯甲基-1,2,3-噻二唑,
2-氰硫基甲硫基苯并噻唑,
1,4-二氯-2,5-二甲氧基苯,
4-(2-氯苯基亚肼基)-3-甲基-5-异恶唑酮,
2-硫代吡啶1-氧化物,
8-羟基喹啉及其铜盐,
2,3-二氢-5-(碳化N,N′-草酰二苯胺基)-6-甲基-1,4-氧硫杂环已炔(oxathiyne),
2,3-二氢-5-(碳化N,N′-草酰二苯胺基)-6-甲基-1,4-氧硫杂环已炔4,4-二氧化物,
2-甲基-5,6-二氢-4H-吡喃-3-碳化N,N′-草酰二苯胺(carboxanilide),
2-甲基呋喃-3-碳化N,N′-草酰二苯胺,
2,5-二甲基呋喃-3-碳化N,N′-草酰二苯胺,
2,4,5-三甲基呋喃-3-碳化N,N′-草酰二苯胺,
2,5-二甲基-N-环已基呋喃-3-甲酰胺
N-环已基-N-甲氧基-2,5-二乙基呋喃-3-甲酰胺,
2-甲基-N-苯甲酰苯胺,
2-碘-N-苯甲酰苯胺,
N-甲酰基-N-吗啉-2,2,2-三氯乙基缩醛,哌嗪-1,4-二基双-(1-(2,2,2-三氯乙基)甲酰胺),1-(3,4-二氯苯胺基)-1-甲酰氨基-2,2,2-三氯乙烷,
2,6-二甲基-N-三癸基吗啉及其盐,
2,6-二甲基-N-环十二烷基吗啉及其盐,
N-[3-(对叔丁基苯基)-2-甲基丙基]-顺-2,6-二甲基吗啉,
N-[3-(对叔丁基苯基)]-2-甲基丙基哌啶,
1-[2-(2,4-二氯苯基)-4-乙基-1,3-二氧戊环-2-基-乙基]-1H-1,2,4-三唑,
1-[2-(2,4-二氯苯基)-4-正丙基-1,3-二氧戊环-2-基-乙基]-1H-1,2,4-三唑,
N-正丙基-N-(2,4,6-三氯苯氧基乙基)-N′-咪唑基脲,
1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)丁-2-酮,
1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)丁-2-醇,
α-(2-氯苯基)-α-(4-氯苯基)-5-嘧啶甲醇,
5-丁基-(2-二甲氨基-4-羟基-6-甲基嘧啶,
双(对氯苯基)-3-哌啶甲醇,
1,2-双(3-乙氧羰基-2-硫脲基)苯,
1,2-双(3-甲氧羰基-2-硫脲基)苯,和
各种杀真菌剂,例如
十二烷基胍乙酸盐,
3-[3-(3,5-二甲基-2-氧环已基)-2-羟乙基]戊二酰胺,六氯苯,
DL-N-(2,6-二甲基苯基)-N-呋喃-2-基丙氨酸甲酯,
DL-N-(2,6-二甲基苯基)-N-(2′-甲氧乙酰基)丙氨酸甲酯,
N-(2,6-二甲基苯基)-N-氯乙酰基-DL-2-氨基丁内酯,
DL-N-(2,6-二甲基苯基)-N-(苯基乙酰基)丙氨酸甲酯,
5-甲基-5-乙烯基-3-(3,5-二氯苯基)-2,4-二氧代-1,3-噁唑烷,
3-(3,5-二氯苯基]-5-甲基-5-甲氧基甲基-1,3-恶唑烷-2,4-二酮,
3-[3,5-二氯苯基)-1-异丙基氨基甲酰基乙内酰脲,
N-(3,5-二氯苯基)-1,2-二甲基环丙烷-1,2-甲酰亚胺,
2-氰基-[N-(乙氨基羰基)-2-甲氧亚氨基]乙酰胺,
1-[2-(2,4-二氯苯基)戊基]-1H-1,2,4三唑,
2,4-二氟-α-(1H-1,2,4-三唑-1-基甲基)二苯甲醇,
N-(3-氯-2,6-二硝基-4-三氟甲基苯基)-5-三氟甲基-3-氯-2-氨基吡啶,
1-((双-(4-氟苯基)甲基甲硅烷基)甲基)-1H-1,2,4-三唑。
合成实施例
使用下面合成实施例中给出的方法,经过适当改进起始物质之后,进一步得到化合物Ⅰ。这样得到的化合物连同其物理数据在下表中给出。
实施例1
邻甲酰苯基二羟乙酸甲酯-0-甲肟(化合物A)
将32g(0.236mol)水合N-甲基吗啉-N-肟加到20g(0.07mol)2-溴甲基苯基二羟乙酸甲酯-0-甲肟的CCl4(300ml)溶液中。将混合物回流4小时,然后冷却。用水及10%浓度盐酸洗涤、干燥并蒸发。用环已烷/乙酸乙酯硅胶色谱纯化后,剩余9.5g(61%)醛(A),为无色固体。
1H-NMR(CDCl3/TMS):δ=3.86,4.01(s,3H),7.32-7.93(m,4H),9.88 ppm(s,1H).
实施列2
2-(甲酰基羟基氨基)苯基二羟乙酸甲酯-0-甲肟(化合物B)
在60-70℃,将10g(45mmol)醛A分批加入到7.15g(67.5mol)Na2CO3和4.7g(67.5mmol)盐酸羟胺的异丙醇(50ml)溶液中。加完后将混合物冷却并在室温下搅拌过夜。将混合物蒸发,将残余物溶于乙酸乙酯中,用水洗涤、干燥并蒸发。用环已烷/乙酸乙酯色谱纯化,剩余7.5g(71%)肟(B)。
1H-NMR(CDCl3/TMS):δ=3.86,4.03(s,3H),7.20-7.68(m,4H),8.00(s,1H),8.34 ppm(br,1H).
实施例3
2-羟基羰基苯基二羟乙酸甲酯-0-甲肟(化合物C)。
将10g(45mmol)化合物A、5.5g(55mmol)三氧化铬和100ml浓乙酸在50℃搅拌2小时。将混合物冷却,然后用水稀释,用乙酸乙酯提取,干燥并蒸发。剩余9.9g(92.5%)苯甲酸C,为油状物。
1H-NMR(DMSO-d6):δ=3.70,3.89(s,3H),7.28-7.89(m,4H),12.8 ppm(br,1H).
实施例4
2-氯代羰基苯基二羟乙酸甲酯-0-甲肟(化合物D)
在-10~0℃,将1.1g(9.3mmol)亚硫酰氯滴加到苯甲酸C(2g,8.43mmol)和吡啶(1.3g,16.4mmol)的甲基叔丁基醚(20ml)和二氯甲烷(10ml)溶液中。将混合物升温至室温,然后在室温(RT)下搅拌过夜。减压除去溶剂。粗产物可直接用于进一步反应。
实施例5
2-溴代苯基二羟乙酸甲酯-0-甲肟(化合物E)
将5.2g(62mmol)0-甲基羟胺盐酸加入到2-溴代苯基二羟乙酸甲酯(10g,41mmol)的甲醇(30ml)溶液中,并将混合物回流2小时。蒸发混合物,将残余物溶于乙酸乙酯中并用水洗涤。干燥并蒸发后,剩余6.9g(62%)化合物E。
1H-NMR(CDCl3/TMS)δ=3.88,4.07(s,3H),7.17-7.61ppm(m,4H).
实施例6
2-乙炔基苯基二羟乙酸甲酯-0-甲肟(化合物F)
将33.3g(0.35mol)三甲基甲硅烷基乙炔、3.8g乙酸钯(Ⅱ)、3.2g碘化铜和8.9g三苯膦加入到55.4g(0.23mol)2-溴代苯基二羟乙酸甲酯在415ml三乙胺中的溶液之中,并对溶液通氮30分钟。然后将反应混合物在90℃加热45分钟。将混合物冷却并过滤。蒸发滤液,溶于乙酸乙酯中并用水洗涤。将有机相干燥并蒸发。剩余56.8gα-酮酯,为黑色油状物。
将如此制得的粗产物溶于50ml甲醇中,加入38.9g(0.37mol)0-甲基羟胺盐酸盐,并将混合物在60℃加热15分钟。蒸发混合物,将残余物溶于乙酸乙酯中并用水洗涤。将有机相干燥并蒸发。剩余52.4g三甲基甲硅烷基化合物,为黑色油状物。
1H-NMR(CDCl3/TMS):δ=0.22(s,9H,SiMe3);3.86;4.06(s,3H,OCH3);7.25-7.61 ppm(m,4H,芳基).
将如此制备的三甲基甲硅烷基乙炔化合物溶于320ml甲醇中,并在室温(20℃)下与3.2g碳酸钾一同搅拌1小时。蒸发混合物,将残余物溶于二氯甲烷中并用浓度为10%的碳酸钠溶液洗涤。将有机相干燥并蒸发。残余36g(72%,基于2-溴苯基二羟乙酸甲酯计算)化合物F,为黑色固体。
1H-NMR(CDCl3/TMS):δ=3.17(s,3H,≡C-H);3.87;4.07(s,3H,OCH3);7.27-7.60ppm(m,4H,芳基).
实施例7
2-(5-苯基异噁唑-3-基)苯基二羟乙酸甲酯-0-甲肟(化合物37,表Ⅰ)。
将5.7g(7.6mmol)次氯酸钠和3滴稀氢氧化钠加到在20ml二氯甲烷中的700mg(7.6mmol)苯基乙炔和1.2g(5mmol)化合物B中,并将混合物在室温下搅拌过夜。分出二氯甲烷相并蒸发。用环已烷/乙酸乙酯硅胶色谱纯化后,得到700mg(42%)化合物37(表Ⅰ),为油状物。
1H-NMR(CDCl3/TMS):δ=3.80,4.01(s,3H),6.67(s,2H),7.35-7.80ppm(m,9H).
实施例8
2-[3-(2-甲苯基)异噁唑-5-基]苯基二羟乙酸甲酯-0-甲肟(化合物38,表Ⅰ)
将4.5g次氯酸钠加到在50ml二氯甲烷中的1g(3.15mmol)化合物F和600mg(4.73mmol)2-甲基苯甲醛肟中,并将整个体系在室温搅拌1小时。分出有机相、干燥并蒸发,硅胶色谱纯化后得到1g化合物38(表Ⅰ),为油状物。
1H-NMR(CDCl3/TMS):δ=2.48,3.79,4.02(s,3H),6.52(s,1H),7.26-7.94 ppm(8H).
实施例9
2-[5-(3-甲苯基)-1,3,4-恶二唑-2-基]苯基二羟乙酸甲酯-0-甲肟(化合物50,表Ⅰ)。
a)将2g(13.6mmol)3-甲基苯基腙加到化合物A(3g,13.6mmol)的甲醇(100ml)溶液中,并将整个体系在室温下搅拌过夜。将沉淀出的固体抽滤、用二异丙醚洗涤并减压干燥。得到3.6g(75%)亚氨基腙,为固体。M.P.:231-233℃。
b)将4.2g(9.5mmol)四乙酸铅加入到1.6g(4.5mmol)亚氨腙化合物(1.6g,4.5mmol,按a制备)的氯仿(100ml)溶液中,并将整个体系在室温下搅拌过夜。加入750ml水,分出有机相,干燥并蒸发。剩余1.5g(95%)化合物50(表Ⅰ),为固体。M.P.:166-167℃。
实施例10
2-(噻唑-2-基)苯基二羟乙酸甲酯-0-甲肟(化合物1,表Ⅰ)
在氮气气氛下,将1.7g 2-三乙基甲锡烷基噻唑加入到1.4g(5.1gmmol)溴化合物(化合物E)、100mg氯化钯(Ⅱ)和310mg三苯膦在30ml四氢呋喃中的混合物中,并将整个体系回流2小时。然后将混合物过滤并蒸发。用环已烷/乙酸乙酯硅胶色谱纯化后,剩余700mg(49%)化合物1(表Ⅰ),为油状物。
1H-NMR(CDCl3/TMS)δ=3.75,3.97(s,3H),7.28-7.86 ppm(m,6H).
实施例11
2-[5-环已基-1,3,4-噻二唑-2-基]苯基二羟乙酸甲酯-0-甲肟(化合物48,表Ⅰ)
在0℃,将在25ml甲醇中的3.6g二硫代环已烷甲酸甲酯加到水合肼(2.1g)的水(7ml)溶液中。将混合物搅拌10分钟,然后倾入到100ml水中。然后用10%(浓度)盐酸中和,用甲基叔丁基醚萃取、干燥并蒸发。将残余物溶于50ml乙腈中。在0℃,滴入5.5g(23mmol)化合物D在30ml乙腈中的溶液,将混合物回流2小时。然后加入二氯甲烷,并将混合物用饱和NaHCO3溶液、水洗涤、干燥并蒸发。
用环已烷/乙酸乙酯硅胶色谱纯化后,剩余3.5g(49%)化合物8(表Ⅰ),为油状物。
1H-NMR(CDCl3/TMS)δ=1.26-3.21(m,11H),3.81,3.96(s,3H)7.30-7.81ppm(m,4H).
实施例12
2-[苯并噻唑-2-基]苯基二羟乙酸甲酯-0-甲肟(化合物2,表Ⅰ)
a)在-78℃,氮气气氛下,将1.5当量正丁基锂滴入2-苯并噻唑-2-基溴苯(2g,6.9mmol)的THF(20ml)溶液中。在此温度下将混合物搅拌1小时,然后加入在20ml THF中的1.6g草酸二甲酯。让混合物升温,加入水,并用甲基叔丁基醚萃取混合物。用已烷/甲基叔丁基进行醚硅胶色谱纯化后剩余300mg(15%)相应的苯基酮酯。
1H-NMR(CDCl3/TMS):δ=3.76,3.99(s,3H),7.35-8.03 ppm(m,8H).
使用实施例
在下列使用实施例中,为进行比较而使用了下列化合物:EP-A254426的2-(2-苯基苯基)二羟乙酸甲酯-0-甲氧翁(A)和EP-A178826公开的2-(2-苯基苯基)-3-甲氧丙烯酸甲酯(B)。
使用实施例1
对葡萄生单轴菌的作用
将包含(干基)80%活性成分和20%乳化剂含水悬浮液喷淋在Maller-Thurgau品种的盆栽葡萄的叶上。为评估作用的延续性,在喷啉涂层已干燥之后将植物在温室中培育8天。然后将叶子用葡萄生单轴菌的游动孢子悬浮液侵染。先将植物在24℃水蒸气饱和的室中放置48小时,然后在20-30℃温室中放置5天。为加速并强化孢囊孢子排出,然后再将植物在潮湿室中放置16小时。然后评估在叶子的阴暗面上受真菌侵害的程度。
结果表明:表Ⅰ中化合物21、32、37、38、39、40和45在用作含63ppm活性成分的喷啉液时,杀真菌作用(95%)优于先有技术活性成分A和B(70%)。
使用实施例2
对Pyricularia oryzae的作用(防护型)
用包含(干基)80%活性成分和20%乳化剂的含水乳液对“Tai Nong”品种的盆生稻苗叶进行喷淋,24小时后用Pyricularia oryzae的含水孢子悬浮液接种。然后将植物在22-24℃,相对湿度95-99%的人工气候保温箱中培育。6天后评估受真菌侵害的程度。
结果表明:化合物20、40、41、42、43、44、45、46和50在作为含250ppm活性成分的喷淋液施用时,其杀真菌作用(85%)优于先有技术活性成分A(20%)。
Claims (10)
1、式Ⅰ二芳基衍生物:
式中
A是=CHOR′,=CHSR′,=CHR′,=CHCl或=NOR′,
B是OR2,SR2或NR2R3,
Het是可带有1-3个R基团的单环、双环或三环的5元或6元杂环结构。
R是卤素、硝基、氰基、CO2R4、NR4R5、CONR4R5、S(O)nR4P(O)(OR4)2、取代或未取代的C1-6烷基、C1-4卤代烷基、取代或未取代的C3-6环烷基、C1-4烷氧基C1-4烷基、C1-4烷硫基C1-4烷基、取代或未取代的C2-6链烯基、取代或未取代的C2-6炔基、C1-6烷氧基、C1-4硫代烷氧基、取代或未取代的苄硫基、C1-4烷基羰基、取代或未取代的苯基羰基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的芳硫基、取代或未取代的芳基C1-4烷基、取代或未取代的芳基C2-4链烯基、取代或未取代的芳基C2-4炔基、取代或未取代的芳氧基C1-4烷基、取代或未取代的芳硫基C1-4烷基、取代或未取代的杂芳基、取代或未取代的杂芳氧基、取代或未取代的杂芳基C1-4烷基、取代或未取代的杂芳基C2-4链烯基、取代或未取代的杂芳氧基C1-4烷基,
“取代或未取代的”所指的取代基是卤素、氰基、硝基、C1-4烷基、C1-4烷氧基、C1-4卤代烷基、C1-4卤代烷氧基或C1-4烷氧基亚氨基C1-2烷基,
其中
n是0,1或2。
R1,R2,R3,R4,R5相同或不同,各自是氢或C1-4烷基,
U,V,W相同或不同,各自是卤素、C1-4烷基或C1-4烷氧基。
2、一种杀虫剂,它含有固体或液体载体和杀真菌有效量的权利要求1所述的通式Ⅰ二芳基衍生物。
3、一种抗真菌的方法,其中用杀真菌有效量的权利要求1所述的通式Ⅰ二芳基衍生物处理真菌或受真菌威协的植物、种子、材料或土壤。
4、权利要求1所述的式Ⅰ化合物,其中A是NOCH3,B是OCH3,Het是异噁唑基-3,R是5-苯基且U,V,W是氢。
5、权利要求1所述的式Ⅰ化合物,其中A是NOCH3,B是OCH3,Het是异噁唑基-5,R是3-(2-甲基苯基),且U,V,W是氢。
6、权利要求1所述的式Ⅰ化合物,其中A是NOCH3,B是OCH3,Het是1,3,4-噁二唑基-2,R是5-(3-甲基苯基),且U,V,W是氢。
7、权利要求1所述的式Ⅰ化合物,其中A是NOCH3,B是OCH3,Het是噻唑基-2,且U,V,W是氢。
8、权利要求1所述的式Ⅰ化合物,其中A是NOCH3,B是OCH3,Het是1,3,4-噻二唑基-2,R是5-环已基,且U,V,W是氢。
9、权利要求1所述的式Ⅰ化合物,其中A是NOCH3,B是OCH3,Het是苯并噻唑基-2,且U,V,W是氢。
10、一种抗真菌的方法,其中使杀虫有效量的权利要求1所述的式Ⅰ二芳基化合物作用于昆虫、线虫或螨或其栖息地。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DEP4313267.7 | 1993-04-23 | ||
DE4313267A DE4313267A1 (de) | 1993-04-23 | 1993-04-23 | Diarylderivate und deren Verwendung als Pflanzenschutzmittel |
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CN1101040A true CN1101040A (zh) | 1995-04-05 |
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CN94105153A Pending CN1101040A (zh) | 1993-04-23 | 1994-04-23 | 二芳基衍生物及其作为作物保护剂的应用 |
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Country | Link |
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US (2) | US5594020A (zh) |
EP (1) | EP0621277A3 (zh) |
JP (1) | JPH0748347A (zh) |
CN (1) | CN1101040A (zh) |
AU (1) | AU673053B2 (zh) |
CA (1) | CA2121979A1 (zh) |
DE (1) | DE4313267A1 (zh) |
HU (1) | HUT67183A (zh) |
IL (1) | IL109335A0 (zh) |
NZ (1) | NZ260366A (zh) |
ZA (1) | ZA942800B (zh) |
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TW201029997A (en) * | 2008-12-23 | 2010-08-16 | Basf Se | Imine compounds for combating invertebrate pests |
CN108137568A (zh) * | 2015-10-13 | 2018-06-08 | 日本农药株式会社 | 具有肟基的稠杂环化合物或其盐类及含有该化合物的农业园艺用杀虫剂以及其使用方法 |
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US3816443A (en) * | 1972-02-17 | 1974-06-11 | Merck & Co Inc | 4-(benzothiazol-2-yl)fluoro phenyl-acetic acids |
US3947582A (en) * | 1973-08-16 | 1976-03-30 | Merck & Co., Inc. | Phenylacetic acid compounds in treating abnormal platelet aggregation |
DE3823991A1 (de) * | 1988-07-15 | 1990-02-15 | Basf Ag | Heterocyclisch substituierte (alpha)-aryl-acrylsaeureester und fungizide, die diese verbindungen enthalten |
DE3835028A1 (de) * | 1988-10-14 | 1990-04-19 | Basf Ag | Oximether-derivate, verfahren zu ihrer herstellung und diese enthaltende fungizide |
US5112860A (en) * | 1989-11-16 | 1992-05-12 | Basf Aktiengesellschaft | Thiocarboxylic esters and fungicides containing them |
DE4030038A1 (de) * | 1990-09-22 | 1992-03-26 | Basf Ag | Ortho-substituierte phenylessigsaeureamide |
DE4103695A1 (de) * | 1991-02-07 | 1992-08-13 | Basf Ag | Oximether und diese enthaltende fungizide |
DE4116090A1 (de) * | 1991-05-17 | 1992-11-19 | Basf Ag | (alpha)-phenylacrylsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen und schadpilzen |
DE4126994A1 (de) * | 1991-08-16 | 1993-02-18 | Basf Ag | (alpha)-arylacrylsaeurederivate, ihre herstellung und verwendung zur bekaempfung von schaedlingen und pilzen |
JP3217191B2 (ja) * | 1992-07-16 | 2001-10-09 | ビーエーエスエフ アクチェンゲゼルシャフト | ヘテロ芳香族化合物およびこれを含有する植物保護剤 |
EP0581095A2 (de) * | 1992-07-24 | 1994-02-02 | BASF Aktiengesellschaft | Substituierte Acrylsäureester und diese enthaltende Pflanzenschutzmittel |
IT1263751B (it) * | 1993-02-05 | 1996-08-27 | Mini Ricerca Scient Tecnolog | Derivati di esteri arilacetici ad attivita' fungicida |
IL109785A0 (en) * | 1993-06-03 | 1994-08-26 | Basf Ag | Azine-substituted phenylacetic acid derivatives and fungicidal compositions containing them |
-
1993
- 1993-04-23 DE DE4313267A patent/DE4313267A1/de not_active Withdrawn
-
1994
- 1994-04-08 EP EP94105448A patent/EP0621277A3/de not_active Withdrawn
- 1994-04-18 IL IL10933594A patent/IL109335A0/xx unknown
- 1994-04-21 JP JP6083000A patent/JPH0748347A/ja not_active Withdrawn
- 1994-04-21 NZ NZ260366A patent/NZ260366A/en unknown
- 1994-04-21 AU AU60628/94A patent/AU673053B2/en not_active Ceased
- 1994-04-22 ZA ZA942800A patent/ZA942800B/xx unknown
- 1994-04-22 HU HU9401168A patent/HUT67183A/hu unknown
- 1994-04-22 CA CA002121979A patent/CA2121979A1/en not_active Abandoned
- 1994-04-22 US US08/231,487 patent/US5594020A/en not_active Expired - Fee Related
- 1994-04-23 CN CN94105153A patent/CN1101040A/zh active Pending
-
1995
- 1995-06-07 US US08/479,453 patent/US5719171A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
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DE4313267A1 (de) | 1994-10-27 |
HU9401168D0 (en) | 1994-07-28 |
HUT67183A (en) | 1995-02-28 |
AU6062894A (en) | 1994-10-27 |
US5594020A (en) | 1997-01-14 |
IL109335A0 (en) | 1994-07-31 |
EP0621277A3 (de) | 1995-05-03 |
JPH0748347A (ja) | 1995-02-21 |
CA2121979A1 (en) | 1994-10-24 |
EP0621277A2 (de) | 1994-10-26 |
ZA942800B (en) | 1995-10-23 |
NZ260366A (en) | 1995-12-21 |
AU673053B2 (en) | 1996-10-24 |
US5719171A (en) | 1998-02-17 |
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