IL102674A - History of 4-benzoyl isoxazole, the process for their preparation and herbicides containing the same - Google Patents
History of 4-benzoyl isoxazole, the process for their preparation and herbicides containing the sameInfo
- Publication number
- IL102674A IL102674A IL10267492A IL10267492A IL102674A IL 102674 A IL102674 A IL 102674A IL 10267492 A IL10267492 A IL 10267492A IL 10267492 A IL10267492 A IL 10267492A IL 102674 A IL102674 A IL 102674A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- methoxy
- cyclopropyl
- general formula
- cyclopropylisoxazole
- Prior art date
Links
- 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 title claims abstract description 6
- 239000000203 mixture Substances 0.000 title claims description 62
- 230000002363 herbicidal effect Effects 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 33
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 9
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 88
- 241000196324 Embryophyta Species 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000003085 diluting agent Substances 0.000 claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- -1 methoxy, ethoxy Chemical group 0.000 claims description 11
- 239000000843 powder Substances 0.000 claims description 10
- 239000012141 concentrate Substances 0.000 claims description 8
- 150000002545 isoxazoles Chemical class 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 5
- 239000004550 soluble concentrate Substances 0.000 claims description 5
- ADEDOCZWFDUTFA-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-methoxy-4-methylsulfanylphenyl)methanone Chemical compound COC1=CC(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 ADEDOCZWFDUTFA-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- FCCQSHVEFQNQJK-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-methoxy-4-methylsulfinylphenyl)methanone Chemical compound COC1=CC(S(C)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 FCCQSHVEFQNQJK-UHFFFAOYSA-N 0.000 claims description 3
- AMJWNUWJYLOEOY-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-methoxy-4-methylsulfonylphenyl)methanone Chemical compound COC1=CC(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 AMJWNUWJYLOEOY-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-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
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000004546 suspension concentrate Substances 0.000 claims description 3
- MBTHBNVEOFKHAG-UHFFFAOYSA-N (3-chloro-2-methyl-4-methylsulfanylphenyl)-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CC1=C(Cl)C(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 MBTHBNVEOFKHAG-UHFFFAOYSA-N 0.000 claims description 2
- BRVPUHLWOLYFEP-UHFFFAOYSA-N (3-chloro-2-methyl-4-methylsulfinylphenyl)-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CC1=C(Cl)C(S(C)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 BRVPUHLWOLYFEP-UHFFFAOYSA-N 0.000 claims description 2
- YCAKZSFSGXUGOP-UHFFFAOYSA-N (3-chloro-2-methyl-4-methylsulfonylphenyl)-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CC1=C(Cl)C(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 YCAKZSFSGXUGOP-UHFFFAOYSA-N 0.000 claims description 2
- BXJQEJJBELAQJI-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2,3-dimethyl-4-methylsulfanylphenyl)methanone Chemical compound CC1=C(C)C(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 BXJQEJJBELAQJI-UHFFFAOYSA-N 0.000 claims description 2
- RKXCRKDIQJPVGD-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2,3-dimethyl-4-methylsulfinylphenyl)methanone Chemical compound CC1=C(C)C(S(C)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 RKXCRKDIQJPVGD-UHFFFAOYSA-N 0.000 claims description 2
- UCQUZVOEOPLHQP-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2,3-dimethyl-4-methylsulfonylphenyl)methanone Chemical compound CC1=C(C)C(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 UCQUZVOEOPLHQP-UHFFFAOYSA-N 0.000 claims description 2
- MPBUWVXWJPIEME-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-ethoxy-4-methylsulfanylphenyl)methanone Chemical compound CCOC1=CC(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 MPBUWVXWJPIEME-UHFFFAOYSA-N 0.000 claims description 2
- PRCLHEFBIJCRLY-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-ethoxy-4-methylsulfonylphenyl)methanone Chemical compound CCOC1=CC(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 PRCLHEFBIJCRLY-UHFFFAOYSA-N 0.000 claims description 2
- PMLWINRFXQKVTJ-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-ethyl-4-methylsulfanylphenyl)methanone Chemical compound CCC1=CC(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 PMLWINRFXQKVTJ-UHFFFAOYSA-N 0.000 claims description 2
- AGOSXOMNJREAQA-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-ethyl-4-methylsulfinylphenyl)methanone Chemical compound CCC1=CC(S(C)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 AGOSXOMNJREAQA-UHFFFAOYSA-N 0.000 claims description 2
- HAIZXMNVDGIOTQ-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-ethyl-4-methylsulfonylphenyl)methanone Chemical compound CCC1=CC(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 HAIZXMNVDGIOTQ-UHFFFAOYSA-N 0.000 claims description 2
- NFGRUWIOVILXPH-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-methyl-4-methylsulfanylphenyl)methanone Chemical compound CC1=CC(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 NFGRUWIOVILXPH-UHFFFAOYSA-N 0.000 claims description 2
- MPZVDOLZUCZOBV-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-methyl-4-methylsulfinylphenyl)methanone Chemical compound CC1=CC(S(C)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 MPZVDOLZUCZOBV-UHFFFAOYSA-N 0.000 claims description 2
- QGFKHAVVXBWHKK-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(2-methyl-4-methylsulfonylphenyl)methanone Chemical compound CC1=CC(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 QGFKHAVVXBWHKK-UHFFFAOYSA-N 0.000 claims description 2
- RFBCWXUXYILQBT-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(3-methoxy-2-methyl-4-methylsulfanylphenyl)methanone Chemical compound COC1=C(SC)C=CC(C(=O)C2=C(ON=C2)C2CC2)=C1C RFBCWXUXYILQBT-UHFFFAOYSA-N 0.000 claims description 2
- FODPMENGJVZYCN-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-(3-methoxy-2-methyl-4-methylsulfonylphenyl)methanone Chemical compound C1=C(S(C)(=O)=O)C(OC)=C(C)C(C(=O)C2=C(ON=C2)C2CC2)=C1 FODPMENGJVZYCN-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000004563 wettable powder Substances 0.000 claims description 2
- DBHUYJCAQSXWBZ-UHFFFAOYSA-N [5-(1-methylcyclopropyl)-1,2-oxazol-4-yl]-(2-methyl-4-methylsulfonylphenyl)methanone Chemical compound CC1=CC(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2(C)CC2)ON=C1 DBHUYJCAQSXWBZ-UHFFFAOYSA-N 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 5
- 239000007787 solid Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000969 carrier Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229940126062 Compound A Drugs 0.000 description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000011149 active material Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
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- 239000004033 plastic Substances 0.000 description 4
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- 239000000377 silicon dioxide Substances 0.000 description 4
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 4
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- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 3
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- 235000007320 Avena fatua Nutrition 0.000 description 3
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- 244000058871 Echinochloa crus-galli Species 0.000 description 3
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- 240000005702 Galium aparine Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
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- 244000067505 Xanthium strumarium Species 0.000 description 3
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- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 3
- 235000009973 maize Nutrition 0.000 description 3
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 238000010790 dilution Methods 0.000 description 2
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
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- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
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- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
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- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
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- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
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- RMGVZKRVHHSUIM-UHFFFAOYSA-L dithionate(2-) Chemical compound [O-]S(=O)(=O)S([O-])(=O)=O RMGVZKRVHHSUIM-UHFFFAOYSA-L 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
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- 230000008018 melting Effects 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
- BAZZERBWEWNHPP-UHFFFAOYSA-N methyl n-(1-butyl-4-carbamoylbenzimidazol-2-yl)carbamate Chemical compound C1=CC=C2N(CCCC)C(NC(=O)OC)=NC2=C1C(N)=O BAZZERBWEWNHPP-UHFFFAOYSA-N 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
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- 125000001979 organolithium group Chemical group 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 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
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- 150000002989 phenols Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
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- 125000006239 protecting group Chemical group 0.000 description 1
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 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
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- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 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
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919116833A GB9116833D0 (en) | 1991-08-05 | 1991-08-05 | Compositions of matter |
| US85042492A | 1992-03-12 | 1992-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL102674A true IL102674A (en) | 1996-11-14 |
Family
ID=26299355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10267492A IL102674A (en) | 1991-08-05 | 1992-07-30 | History of 4-benzoyl isoxazole, the process for their preparation and herbicides containing the same |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP0527037B1 (fr) |
| CN (2) | CN1042334C (fr) |
| AT (1) | ATE144256T1 (fr) |
| AU (1) | AU654729B2 (fr) |
| BG (1) | BG61162B1 (fr) |
| BR (1) | BR9203099A (fr) |
| CA (1) | CA2075347A1 (fr) |
| CZ (1) | CZ241392A3 (fr) |
| DE (1) | DE69214557T2 (fr) |
| DK (1) | DK0527037T3 (fr) |
| EG (1) | EG19867A (fr) |
| ES (1) | ES2093205T3 (fr) |
| FI (1) | FI923514A (fr) |
| GR (1) | GR3021391T3 (fr) |
| HR (1) | HRP920255A2 (fr) |
| HU (1) | HU212433B (fr) |
| IL (1) | IL102674A (fr) |
| MA (1) | MA22609A1 (fr) |
| MX (1) | MX9204525A (fr) |
| NZ (1) | NZ243816A (fr) |
| RO (1) | RO111679B1 (fr) |
| SI (1) | SI9200164A (fr) |
| SK (1) | SK241392A3 (fr) |
| TR (1) | TR27253A (fr) |
| YU (1) | YU74792A (fr) |
| ZW (1) | ZW12592A1 (fr) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9116834D0 (en) * | 1991-08-05 | 1991-09-18 | Rhone Poulenc Agriculture | Compositions of new matter |
| US5334753A (en) * | 1992-03-12 | 1994-08-02 | Rhone-Poulenc Agriculture Ltd | Processes for preparing ortho-substituted benzoic acids |
| HRP930105A2 (en) * | 1992-03-12 | 1996-04-30 | Rhone Poulenc Agriculture | New herbicides |
| EP0674629B1 (fr) | 1992-12-18 | 1998-07-08 | Rhone-Poulenc Agriculture Ltd. | Derives 4-benzoylisoxazole et leur utilisation comme herbicides |
| GB9302049D0 (en) * | 1993-02-03 | 1993-03-24 | Rhone Poulenc Agriculture | Compositions of new matter |
| GB9302072D0 (en) * | 1993-02-03 | 1993-03-24 | Rhone Poulenc Agriculture | New compositions of matter |
| CA2117413C (fr) * | 1993-07-30 | 2006-11-21 | Neil Geach | Derives herbicides isoxazole-4-yl-methanone |
| GB9316689D0 (en) * | 1993-08-11 | 1993-09-29 | 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 |
| DE4427998A1 (de) * | 1994-08-08 | 1996-02-15 | Basf Ag | Saccharinderivate |
| US5627131A (en) * | 1995-01-09 | 1997-05-06 | Zeneca Limited | Herbicidal compositions of 4-benzoylisoxazole and antidotes therefor |
| WO1997000014A1 (fr) * | 1995-06-19 | 1997-01-03 | Rhone-Poulenc Agrochimie | Utilisation de 4-benzoylisoxazoles pour la protection du gazon |
| GB9606015D0 (en) * | 1996-03-22 | 1996-05-22 | Rhone Poulenc Agriculture | New herbicides |
| 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 |
| DE19614856A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide heterocyclisch anellierte Benzoylisothiazole |
| US6297198B1 (en) | 1996-05-14 | 2001-10-02 | Syngenta Participations Ag | Isoxazole derivatives and their use as herbicides |
| GB9714305D0 (en) | 1997-07-07 | 1997-09-10 | Rhone Poulenc Agrochimie | Chemical process |
| US5863865A (en) * | 1997-10-28 | 1999-01-26 | Zeneca Limited | Herbicidal 4-benzoylisoxazoles derivatives |
| GB2335658A (en) * | 1998-03-25 | 1999-09-29 | Rhone Poulenc Agriculture | Processes for preparing 1-aryl-3-cyclopropyl-propane-1,3-dione intermediates |
| 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 |
| DE19920791A1 (de) | 1999-05-06 | 2000-11-09 | Bayer Ag | Substituierte Benzoylisoxazole |
| TR200200590T2 (tr) | 1999-09-08 | 2002-06-21 | Aventis Cropscience Uk Limited | Yeni herbisidal kompozisyonlar |
| US6545185B1 (en) | 2001-03-29 | 2003-04-08 | Eagleview Technologies, Inc. | Preparation of ketones from aldehydes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9025469D0 (en) * | 1990-11-22 | 1991-01-09 | Rhone Poulenc Agriculture | New compositions of matter |
| GB8920519D0 (en) * | 1989-09-11 | 1989-10-25 | Rhone Poulenc Ltd | New compositions of matter |
-
1992
- 1992-07-30 IL IL10267492A patent/IL102674A/en not_active IP Right Cessation
- 1992-07-31 YU YU74792A patent/YU74792A/sh unknown
- 1992-08-03 ZW ZW125/92A patent/ZW12592A1/xx unknown
- 1992-08-03 SK SK2413-92A patent/SK241392A3/sk unknown
- 1992-08-03 AU AU20731/92A patent/AU654729B2/en not_active Ceased
- 1992-08-03 CZ CS922413A patent/CZ241392A3/cs unknown
- 1992-08-03 MA MA22898A patent/MA22609A1/fr unknown
- 1992-08-03 NZ NZ243816A patent/NZ243816A/xx unknown
- 1992-08-04 BG BG96746A patent/BG61162B1/bg unknown
- 1992-08-04 ES ES92307123T patent/ES2093205T3/es not_active Expired - Lifetime
- 1992-08-04 RO RO92-01067A patent/RO111679B1/ro unknown
- 1992-08-04 EG EG44192A patent/EG19867A/xx active
- 1992-08-04 DE DE69214557T patent/DE69214557T2/de not_active Expired - Fee Related
- 1992-08-04 DK DK92307123.7T patent/DK0527037T3/da active
- 1992-08-04 EP EP92307123A patent/EP0527037B1/fr not_active Expired - Lifetime
- 1992-08-04 AT AT92307123T patent/ATE144256T1/de not_active IP Right Cessation
- 1992-08-04 FI FI923514A patent/FI923514A/fi unknown
- 1992-08-04 HU HU9202531A patent/HU212433B/hu not_active IP Right Cessation
- 1992-08-04 MX MX9204525A patent/MX9204525A/es not_active IP Right Cessation
- 1992-08-05 BR BR929203099A patent/BR9203099A/pt not_active Application Discontinuation
- 1992-08-05 HR HR920255A patent/HRP920255A2/hr not_active Application Discontinuation
- 1992-08-05 TR TR00790/92A patent/TR27253A/xx unknown
- 1992-08-05 CN CN92109246.6A patent/CN1042334C/zh not_active Expired - Fee Related
- 1992-08-05 SI SI19929200164A patent/SI9200164A/sl unknown
- 1992-08-05 CA CA002075347A patent/CA2075347A1/fr not_active Abandoned
-
1996
- 1996-05-17 CN CN96107422.1A patent/CN1141295A/zh active Pending
- 1996-10-17 GR GR960401439T patent/GR3021391T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SI9200164A (en) | 1993-03-31 |
| GR3021391T3 (en) | 1997-01-31 |
| NZ243816A (en) | 1995-01-27 |
| SK241392A3 (en) | 1995-02-08 |
| AU2073192A (en) | 1993-02-11 |
| HU212433B (en) | 1996-06-28 |
| TR27253A (tr) | 1994-12-21 |
| EG19867A (en) | 1996-03-31 |
| MA22609A1 (fr) | 1993-04-01 |
| CN1141295A (zh) | 1997-01-29 |
| ATE144256T1 (de) | 1996-11-15 |
| DE69214557D1 (de) | 1996-11-21 |
| BG96746A (bg) | 1993-12-24 |
| CA2075347A1 (fr) | 1993-02-06 |
| BR9203099A (pt) | 1993-03-30 |
| FI923514A (fi) | 1993-02-06 |
| DE69214557T2 (de) | 1997-02-27 |
| ES2093205T3 (es) | 1996-12-16 |
| HRP920255A2 (en) | 1995-08-31 |
| CN1069267A (zh) | 1993-02-24 |
| AU654729B2 (en) | 1994-11-17 |
| EP0527037B1 (fr) | 1996-10-16 |
| MX9204525A (es) | 1993-09-01 |
| EP0527037A1 (fr) | 1993-02-10 |
| CZ241392A3 (en) | 1993-02-17 |
| DK0527037T3 (da) | 1996-11-18 |
| CN1042334C (zh) | 1999-03-03 |
| YU74792A (sh) | 1995-10-03 |
| BG61162B1 (bg) | 1997-01-31 |
| HUT61733A (en) | 1993-03-01 |
| RO111679B1 (ro) | 1996-12-30 |
| FI923514A0 (fi) | 1992-08-04 |
| ZW12592A1 (en) | 1993-09-15 |
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| KB | Patent renewed | ||
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| MM9K | Patent not in force due to non-payment of renewal fees |