SK280521B6 - 4-benzoylizoxazolové deriváty, spôsob ich prípravy - Google Patents
4-benzoylizoxazolové deriváty, spôsob ich prípravy Download PDFInfo
- Publication number
- SK280521B6 SK280521B6 SK64-93A SK6493A SK280521B6 SK 280521 B6 SK280521 B6 SK 280521B6 SK 6493 A SK6493 A SK 6493A SK 280521 B6 SK280521 B6 SK 280521B6
- Authority
- SK
- Slovakia
- Prior art keywords
- benzoyl
- formula
- isoxazole
- cyclopropyl
- compound
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 101
- 241000196324 Embryophyta Species 0.000 claims abstract description 60
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000000460 chlorine Substances 0.000 claims abstract description 32
- 230000012010 growth Effects 0.000 claims abstract description 30
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 24
- 229910052731 fluorine Chemical group 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 125000005843 halogen group Chemical group 0.000 claims abstract description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 21
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 14
- FGGUUGIYSOGQED-UHFFFAOYSA-N 1,2-oxazol-4-yl(phenyl)methanone Chemical class C=1C=CC=CC=1C(=O)C=1C=NOC=1 FGGUUGIYSOGQED-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
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- 239000003085 diluting agent Substances 0.000 claims description 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 239000004094 surface-active agent Substances 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 15
- VHVGFEDTMPYCSX-UHFFFAOYSA-N [1-[[2,2-dimethyl-3-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]propoxy]methyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCC(C)(C)COCN1C=CC(=C[NH+]=O)C=C1 VHVGFEDTMPYCSX-UHFFFAOYSA-N 0.000 claims description 14
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
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- UXYRXGFUANQKTA-UHFFFAOYSA-N 1,2-oxazole-3-carboxylic acid Chemical compound OC(=O)C=1C=CON=1 UXYRXGFUANQKTA-UHFFFAOYSA-N 0.000 claims description 4
- VYIASUOPMNTCHK-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(3,4-dichloro-2-methylsulfinylphenyl)methanone Chemical compound CS(=O)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 VYIASUOPMNTCHK-UHFFFAOYSA-N 0.000 claims description 3
- RPUAUDBVRXGAQZ-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(3,4-difluoro-2-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C1=C(F)C(F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 RPUAUDBVRXGAQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
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- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 239000004546 suspension concentrate Substances 0.000 claims description 3
- YRNUWKXUUMBBMD-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(3,4-dichloro-2-methylsulfanylphenyl)methanone Chemical compound CSC1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 YRNUWKXUUMBBMD-UHFFFAOYSA-N 0.000 claims description 2
- GYFTVSPMBXYEJX-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(3,4-dichloro-2-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 GYFTVSPMBXYEJX-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
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- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
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- SMQJAEWHNYMQLA-UHFFFAOYSA-N ethyl 5-cyclopropyl-4-(3,4-dichloro-2-methylsulfonylbenzoyl)-1,2-oxazole-3-carboxylate Chemical compound C=1C=C(Cl)C(Cl)=C(S(C)(=O)=O)C=1C(=O)C=1C(C(=O)OCC)=NOC=1C1CC1 SMQJAEWHNYMQLA-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
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- 238000006243 chemical reaction Methods 0.000 description 25
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
- 239000000706 filtrate Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 20
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- ZVQSXJRBFRFWRO-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].[Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 ZVQSXJRBFRFWRO-UHFFFAOYSA-N 0.000 description 1
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- UXOLDCOJRAMLTQ-UTCJRWHESA-N ethyl (2z)-2-chloro-2-hydroxyiminoacetate Chemical compound CCOC(=O)C(\Cl)=N\O UXOLDCOJRAMLTQ-UTCJRWHESA-N 0.000 description 1
- MXNGESVSXGJECC-UHFFFAOYSA-N ethyl 2,4-dibromo-3-methoxybenzoate Chemical compound CCOC(=O)C1=CC=C(Br)C(OC)=C1Br MXNGESVSXGJECC-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- ISXSFOPKZQZDAO-UHFFFAOYSA-N formaldehyde;sodium Chemical compound [Na].O=C ISXSFOPKZQZDAO-UHFFFAOYSA-N 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000011968 lewis acid catalyst Substances 0.000 description 1
- NRUBUZBAZRTHHX-UHFFFAOYSA-N lithium;propan-2-ylazanide Chemical compound [Li+].CC(C)[NH-] NRUBUZBAZRTHHX-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 description 1
- YOVLJBSHMOBDEK-UHFFFAOYSA-N methyl 2-fluoro-6-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=C(F)C=CC=C1C(F)(F)F YOVLJBSHMOBDEK-UHFFFAOYSA-N 0.000 description 1
- QAFJIJWLEBLXHH-UHFFFAOYSA-N methyl 2-fluorobenzoate Chemical compound COC(=O)C1=CC=CC=C1F QAFJIJWLEBLXHH-UHFFFAOYSA-N 0.000 description 1
- MJBACRKEVLIFEI-UHFFFAOYSA-N methyl 3-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-methylsulfanyl-6-(trifluoromethyl)benzoate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=C(SC)C(C(=O)C2=C(ON=C2)C2CC2)=C1 MJBACRKEVLIFEI-UHFFFAOYSA-N 0.000 description 1
- PIDSJLQXFNQFTK-UHFFFAOYSA-N methyl 4-chloro-2-fluoro-3-methylbenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C)=C1F PIDSJLQXFNQFTK-UHFFFAOYSA-N 0.000 description 1
- KMSUFAHFENDRAH-UHFFFAOYSA-N methyl 6-chloro-3-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-methylsulfanylbenzoate Chemical compound COC(=O)C1=C(Cl)C=CC(C(=O)C2=C(ON=C2)C2CC2)=C1SC KMSUFAHFENDRAH-UHFFFAOYSA-N 0.000 description 1
- KXUHSVIMPJOSMM-UHFFFAOYSA-N methyl 6-chloro-3-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-methylsulfinylbenzoate Chemical compound COC(=O)C1=C(Cl)C=CC(C(=O)C2=C(ON=C2)C2CC2)=C1S(C)=O KXUHSVIMPJOSMM-UHFFFAOYSA-N 0.000 description 1
- LQQWQIVGAFDANY-UHFFFAOYSA-N methyl 6-chloro-3-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-methylsulfonylbenzoate Chemical compound COC(=O)C1=C(Cl)C=CC(C(=O)C2=C(ON=C2)C2CC2)=C1S(C)(=O)=O LQQWQIVGAFDANY-UHFFFAOYSA-N 0.000 description 1
- XRPYZCLXRAYDLN-UHFFFAOYSA-N methylsulfanyl benzoate Chemical compound CSOC(=O)C1=CC=CC=C1 XRPYZCLXRAYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
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- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CXPRGLWJJQBWRS-UHFFFAOYSA-N tert-butyl 3-cyclopropyl-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1CC1 CXPRGLWJJQBWRS-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85012892A | 1992-03-12 | 1992-03-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK6493A3 SK6493A3 (en) | 1993-10-06 |
| SK280521B6 true SK280521B6 (sk) | 2000-03-13 |
Family
ID=25307335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK64-93A SK280521B6 (sk) | 1992-03-12 | 1993-02-04 | 4-benzoylizoxazolové deriváty, spôsob ich prípravy |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US5334753A (cs) |
| EP (1) | EP0560482B1 (cs) |
| JP (1) | JP3310039B2 (cs) |
| KR (1) | KR100278704B1 (cs) |
| CN (1) | CN1057524C (cs) |
| AT (1) | ATE156483T1 (cs) |
| AU (1) | AU664229B2 (cs) |
| BG (1) | BG62151B1 (cs) |
| BR (1) | BR9300324A (cs) |
| CA (1) | CA2088840C (cs) |
| CZ (1) | CZ282051B6 (cs) |
| DE (1) | DE69312769T2 (cs) |
| DK (1) | DK0560482T3 (cs) |
| ES (1) | ES2105098T3 (cs) |
| FI (1) | FI930496A7 (cs) |
| GR (1) | GR3024373T3 (cs) |
| HR (1) | HRP930106B1 (cs) |
| HU (1) | HU217562B (cs) |
| IL (1) | IL104614A (cs) |
| MA (1) | MA22920A1 (cs) |
| MX (1) | MX9300627A (cs) |
| NZ (1) | NZ245844A (cs) |
| PL (1) | PL172002B1 (cs) |
| RO (1) | RO112029B1 (cs) |
| RU (1) | RU2105761C1 (cs) |
| SI (1) | SI9300063B (cs) |
| SK (1) | SK280521B6 (cs) |
| TR (1) | TR27630A (cs) |
| TW (1) | TW250426B (cs) |
| YU (1) | YU48749B (cs) |
| ZA (1) | ZA93769B (cs) |
| ZW (1) | ZW2293A1 (cs) |
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| GB9115377D0 (en) * | 1991-07-17 | 1991-09-04 | Rhone Poulenc Agriculture | New compositions of matter |
| US5530028A (en) * | 1992-11-23 | 1996-06-25 | Rohm And Haas Company | Insecticidal N'-substituted-N,N'-diacylhydrazines |
| GB9302072D0 (en) * | 1993-02-03 | 1993-03-24 | Rhone Poulenc Agriculture | New compositions of matter |
| GB9325284D0 (en) * | 1993-12-10 | 1994-02-16 | Rhone Poulenc Agriculture | Herbicidal compositions |
| US5962370A (en) * | 1993-12-10 | 1999-10-05 | Rhone-Poulenc Agriculture Ltd | Herbicidal compositions comprising a 4-benzoylisoxazole and a triazine herbicide |
| GB9325618D0 (en) * | 1993-12-15 | 1994-02-16 | Rhone Poulenc Agriculture | New herbicides |
| US5795846A (en) * | 1994-08-01 | 1998-08-18 | Rhone-Poulenc Agriculture Limited | Herbicidal compositions |
| US5552367A (en) * | 1994-11-18 | 1996-09-03 | Rhone-Poulenc Agriculture Ltd. | Synergistic herbicidal compositions comprising 4-benzoylisoxazole and dinitroaniline herbicides |
| US5912206A (en) * | 1994-12-09 | 1999-06-15 | Rhone-Poulenc Agrochimie | Herbicidal compositions |
| WO1997000013A1 (en) * | 1995-06-19 | 1997-01-03 | Rhone-Poulenc Agrochimie | New fungicidal compositions and the use thereof |
| US6004904A (en) * | 1995-06-19 | 1999-12-21 | Rhone-Poulenc Inc. | Use of 4-benzoylisoxazoles for the protection of turfgrass |
| ZA9610348B (en) * | 1995-12-20 | 1997-07-11 | Rhone Poulenc Agriculture | Herbicidal compositions |
| WO1997028122A2 (en) | 1996-02-01 | 1997-08-07 | Rhone-Poulenc Agrochimie | Process for preparing diketone compounds |
| GB9603127D0 (en) * | 1996-02-15 | 1996-04-17 | Rhone Poulenc Agriculture | New process for preparing intermediates |
| EA002126B1 (ru) * | 1996-02-16 | 2001-12-24 | Рон-Пуленк Агро | Новые промежуточные соединения для пестицидов |
| AU2096697A (en) * | 1996-03-15 | 1997-10-10 | Rhone-Poulenc Agrochimie | Herbicidal compositions |
| GB9606015D0 (en) * | 1996-03-22 | 1996-05-22 | Rhone Poulenc Agriculture | New herbicides |
| DE19614856A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide heterocyclisch anellierte Benzoylisothiazole |
| DE19614858A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide heterocyclisch substituierte Benzoylisothiazole |
| DE19614859A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide Benzoylisothiazole |
| US6297198B1 (en) | 1996-05-14 | 2001-10-02 | Syngenta Participations Ag | Isoxazole derivatives and their use as herbicides |
| WO1998051153A1 (en) * | 1997-05-15 | 1998-11-19 | Rhone-Poulenc Agriculture Ltd. | Herbicidal methods and derivatives |
| ZA984938B (en) | 1997-06-10 | 1999-01-04 | Rhone Poulenc Agrochimie | Herbicidal mixtures |
| GB9714302D0 (en) | 1997-07-07 | 1997-09-10 | Rhone Poulenc Agrochimie | Process |
| GB9714305D0 (en) * | 1997-07-07 | 1997-09-10 | Rhone Poulenc Agrochimie | Chemical process |
| US5905057A (en) * | 1997-11-06 | 1999-05-18 | Rhone-Poulenc Agrochimie | Herbicidal 4-benzoylisoxazole-3-carboxylate liquid compositions comprising N-alkylpyrrolidinone stabilizer |
| GB9804986D0 (en) | 1998-03-09 | 1998-05-06 | Rhone Poulenc Agrochimie | New herbicidal compositions |
| US6392099B1 (en) | 1998-11-19 | 2002-05-21 | Eagleview Technologies, Inc. | Method and apparatus for the preparation of ketones |
| US6369276B1 (en) | 1998-11-19 | 2002-04-09 | Eagleview Technologies, Inc. | Catalyst structure for ketone production and method of making and using the same |
| DE19853827A1 (de) | 1998-11-21 | 2000-05-25 | Aventis Cropscience Gmbh | Kombinationen aus Herbiziden und Safenern |
| UA72496C2 (uk) * | 1999-02-01 | 2005-03-15 | Авентіс Агрікалче Лімітед | Спосіб пригнічення росту бур'янів та композиція з уповільненим вивільненням гербіциду |
| IL148337A0 (en) * | 1999-09-08 | 2002-09-12 | Aventis Cropscience Uk Ltd | New herbicidal compositions |
| FR2815969B1 (fr) | 2000-10-30 | 2004-12-10 | Aventis Cropscience Sa | Plantes tolerantes aux herbicides par contournement de voie metabolique |
| US6545185B1 (en) | 2001-03-29 | 2003-04-08 | Eagleview Technologies, Inc. | Preparation of ketones from aldehydes |
| SE0201937D0 (sv) * | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | Therapeutic agents |
| FR2844142B1 (fr) | 2002-09-11 | 2007-08-17 | Bayer Cropscience Sa | Plantes transformees a biosynthese de prenylquinones amelioree |
| AR074941A1 (es) | 2009-01-07 | 2011-02-23 | Bayer Cropscience Sa | Plantas transplastomicas exentas de marcador de seleccion |
| US8153132B2 (en) | 2009-10-30 | 2012-04-10 | Ms Technologies, Inc. | Antibodies immunoreactive with mutant hydroxypenylpyruvate dioxygenase |
| AR080105A1 (es) | 2010-02-02 | 2012-03-14 | Bayer Cropscience Ag | Transformacion de soja usando inhibidores de hidrofenil piruvato dioxigenasa (hppd) como agentes de seleccion |
| CA2798067A1 (en) | 2010-05-04 | 2011-11-24 | Basf Se | Plants having increased tolerance to herbicides |
| CA2820706C (en) | 2010-12-03 | 2018-05-22 | Ms Technologies, Llc | Optimized expression of glyphosate resistance encoding nucleic acid molecules in plant cells |
| US8648230B2 (en) | 2011-03-18 | 2014-02-11 | Ms Technologies, Llc | Regulatory regions preferentially expressing in non-pollen plant tissue |
| AU2013205521B2 (en) | 2012-02-01 | 2016-10-13 | Corteva Agriscience Llc | Synthetic chloroplast transit peptides |
| AP2016009227A0 (en) | 2013-11-04 | 2016-05-31 | Dow Agrosciences Llc | Optimal maize loci |
| JP6560205B2 (ja) | 2013-11-04 | 2019-08-14 | ダウ アグロサイエンシィズ エルエルシー | 最適なダイズ遺伝子座 |
| UY35812A (es) | 2013-11-04 | 2015-05-29 | Dow Agrosciences Llc | ?loci de maíz óptimos?. |
| TW201527312A (zh) | 2013-12-31 | 2015-07-16 | Dow Agrosciences Llc | 新穎玉米泛素啓動子（一） |
| TW201527316A (zh) | 2013-12-31 | 2015-07-16 | Dow Agrosciences Llc | 新穎玉米泛素啓動子（五） |
| TW201527314A (zh) | 2013-12-31 | 2015-07-16 | Dow Agrosciences Llc | 新穎玉米泛素啓動子（三） |
| TW201527313A (zh) | 2013-12-31 | 2015-07-16 | Dow Agrosciences Llc | 新穎玉米泛素啓動子（二） |
| TW201538518A (zh) | 2014-02-28 | 2015-10-16 | Dow Agrosciences Llc | 藉由嵌合基因調控元件所賦予之根部特異性表現 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4323692A (en) * | 1978-08-04 | 1982-04-06 | Rohm And Haas Company | Process for preparing phenoxybenzoic acids |
| GB9017539D0 (en) * | 1990-08-10 | 1990-09-26 | Rhone Poulenc Agriculture | New compositions of matter |
| GB8920519D0 (en) * | 1989-09-11 | 1989-10-25 | Rhone Poulenc Ltd | New compositions of matter |
| GB9025469D0 (en) * | 1990-11-22 | 1991-01-09 | Rhone Poulenc Agriculture | New compositions of matter |
| GB9116834D0 (en) * | 1991-08-05 | 1991-09-18 | Rhone Poulenc Agriculture | Compositions of new matter |
| IL102674A (en) * | 1991-08-05 | 1996-11-14 | Rhone Poulenc Agriculture | 4-Benzoyl isoxazole derivatives process for their preparation and herbicidal compositions containing them |
-
1992
- 1992-12-23 US US07/996,046 patent/US5334753A/en not_active Expired - Lifetime
-
1993
- 1993-02-03 HR HR07/850,128A patent/HRP930106B1/xx not_active IP Right Cessation
- 1993-02-03 TR TR00116/93A patent/TR27630A/xx unknown
- 1993-02-04 NZ NZ245844A patent/NZ245844A/xx unknown
- 1993-02-04 SK SK64-93A patent/SK280521B6/sk unknown
- 1993-02-04 CN CN93101488A patent/CN1057524C/zh not_active Expired - Fee Related
- 1993-02-04 FI FI930496A patent/FI930496A7/fi unknown
- 1993-02-04 ES ES93300816T patent/ES2105098T3/es not_active Expired - Lifetime
- 1993-02-04 SI SI9300063A patent/SI9300063B/sl unknown
- 1993-02-04 RO RO93-00120A patent/RO112029B1/ro unknown
- 1993-02-04 DE DE69312769T patent/DE69312769T2/de not_active Expired - Fee Related
- 1993-02-04 DK DK93300816.1T patent/DK0560482T3/da active
- 1993-02-04 JP JP01761193A patent/JP3310039B2/ja not_active Expired - Fee Related
- 1993-02-04 HU HU9300293A patent/HU217562B/hu not_active IP Right Cessation
- 1993-02-04 ZW ZW22/93A patent/ZW2293A1/xx unknown
- 1993-02-04 ZA ZA93769A patent/ZA93769B/xx unknown
- 1993-02-04 YU YU6593A patent/YU48749B/sh unknown
- 1993-02-04 IL IL104614A patent/IL104614A/xx not_active IP Right Cessation
- 1993-02-04 EP EP93300816A patent/EP0560482B1/en not_active Expired - Lifetime
- 1993-02-04 BG BG97402A patent/BG62151B1/bg unknown
- 1993-02-04 BR BR9300324A patent/BR9300324A/pt not_active IP Right Cessation
- 1993-02-04 AT AT93300816T patent/ATE156483T1/de not_active IP Right Cessation
- 1993-02-04 MX MX9300627A patent/MX9300627A/es not_active IP Right Cessation
- 1993-02-04 PL PL93297644A patent/PL172002B1/pl unknown
- 1993-02-04 RU RU93004513A patent/RU2105761C1/ru active
- 1993-02-04 MA MA23074A patent/MA22920A1/fr unknown
- 1993-02-04 CZ CZ93132A patent/CZ282051B6/cs not_active IP Right Cessation
- 1993-02-04 AU AU32819/93A patent/AU664229B2/en not_active Ceased
- 1993-02-04 CA CA002088840A patent/CA2088840C/en not_active Expired - Fee Related
- 1993-02-04 KR KR1019930001500A patent/KR100278704B1/ko not_active Expired - Fee Related
- 1993-02-06 TW TW082100807A patent/TW250426B/zh active
-
1997
- 1997-08-07 GR GR970401067T patent/GR3024373T3/el unknown
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