CN1039229C - 4-苯甲酰异噁唑衍生物及其除草剂组合物和制备方法 - Google Patents
4-苯甲酰异噁唑衍生物及其除草剂组合物和制备方法 Download PDFInfo
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- CN1039229C CN1039229C CN94101760A CN94101760A CN1039229C CN 1039229 C CN1039229 C CN 1039229C CN 94101760 A CN94101760 A CN 94101760A CN 94101760 A CN94101760 A CN 94101760A CN 1039229 C CN1039229 C CN 1039229C
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- Prior art keywords
- methyl
- benzoyl
- isoxazole
- cyclopropyl
- chloro
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- 239000004009 herbicide Substances 0.000 title abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 165
- 150000001875 compounds Chemical class 0.000 claims description 131
- 239000000203 mixture Substances 0.000 claims description 90
- -1 4-(4-bromo-2-(sulfonyloxy methyl methyl) benzoyl)-5-cyclopropyl isoxazole Chemical class 0.000 claims description 76
- 241000196324 Embryophyta Species 0.000 claims description 62
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 40
- 239000013543 active substance Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 230000002363 herbicidal effect Effects 0.000 claims description 27
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 24
- 125000004494 ethyl ester group Chemical group 0.000 claims description 22
- 230000012010 growth Effects 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 239000003085 diluting agent Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 18
- WNVZOHNNPDZYFN-UHFFFAOYSA-N 1,2-oxazole-3-carbaldehyde Chemical class O=CC=1C=CON=1 WNVZOHNNPDZYFN-UHFFFAOYSA-N 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 230000008635 plant growth Effects 0.000 claims description 7
- PWJBIKGCZAYWGQ-UHFFFAOYSA-N [4-bromo-2-(methylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)CC1=CC(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 PWJBIKGCZAYWGQ-UHFFFAOYSA-N 0.000 claims description 6
- YIRWEZBQCXAEGN-UHFFFAOYSA-N 4-[4-bromo-2-(methylsulfinylmethyl)benzoyl]-5-cyclopropyl-1,2-oxazole-3-carboxylic acid Chemical compound CS(=O)CC1=CC(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1C(O)=O YIRWEZBQCXAEGN-UHFFFAOYSA-N 0.000 claims description 5
- HGPUDLNUBVSVPA-UHFFFAOYSA-N CS(CC(C(Cl)=C(C=C1)S(C)=O)=C1C(C1=C(C2CC2)ON=C1)=O)=O Chemical compound CS(CC(C(Cl)=C(C=C1)S(C)=O)=C1C(C1=C(C2CC2)ON=C1)=O)=O HGPUDLNUBVSVPA-UHFFFAOYSA-N 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
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- HAUZNAUJENNXJM-UHFFFAOYSA-N 4-[3-bromo-2-(methylsulfinylmethyl)benzoyl]-5-cyclopropyl-1,2-oxazole-3-carboxylic acid Chemical compound CS(=O)CC1=C(Br)C=CC=C1C(=O)C1=C(C2CC2)ON=C1C(O)=O HAUZNAUJENNXJM-UHFFFAOYSA-N 0.000 claims description 4
- BHVXNEKSSGWBAE-UHFFFAOYSA-N CS(CC(C(S(C)=O)=C(C=C1)Cl)=C1C(C1=C(C2CC2)ON=C1)=O)=O Chemical compound CS(CC(C(S(C)=O)=C(C=C1)Cl)=C1C(C1=C(C2CC2)ON=C1)=O)=O BHVXNEKSSGWBAE-UHFFFAOYSA-N 0.000 claims description 4
- HKOPOVKCYGPJPE-UHFFFAOYSA-N [2-bromo-4-(methylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound BrC1=CC(CS(=O)C)=CC=C1C(=O)C1=C(C2CC2)ON=C1 HKOPOVKCYGPJPE-UHFFFAOYSA-N 0.000 claims description 4
- NBAIZRLRQLOXEL-UHFFFAOYSA-N [2-chloro-4-(methylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound ClC1=CC(CS(=O)C)=CC=C1C(=O)C1=C(C2CC2)ON=C1 NBAIZRLRQLOXEL-UHFFFAOYSA-N 0.000 claims description 4
- IYRQRPYWOIPXMD-UHFFFAOYSA-N [3-bromo-2-(methylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)CC1=C(Br)C=CC=C1C(=O)C1=C(C2CC2)ON=C1 IYRQRPYWOIPXMD-UHFFFAOYSA-N 0.000 claims description 4
- BJLLGMOFLVWPDL-UHFFFAOYSA-N [3-bromo-4-chloro-2-(methylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)CC1=C(Br)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 BJLLGMOFLVWPDL-UHFFFAOYSA-N 0.000 claims description 4
- NZIWHWZNEGQTAT-UHFFFAOYSA-N [4-bromo-2-(prop-2-enylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound C=CCS(=O)CC1=CC(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 NZIWHWZNEGQTAT-UHFFFAOYSA-N 0.000 claims description 4
- GGUWMQAXOWOXHP-UHFFFAOYSA-N [4-bromo-2-(propylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CCCS(=O)CC1=CC(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 GGUWMQAXOWOXHP-UHFFFAOYSA-N 0.000 claims description 4
- GIQFFCIORWWTJF-UHFFFAOYSA-N [4-chloro-2-(methylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)CC1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 GIQFFCIORWWTJF-UHFFFAOYSA-N 0.000 claims description 4
- OFPBYURDFYQECK-UHFFFAOYSA-N [4-chloro-3-fluoro-2-(methylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)CC1=C(F)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OFPBYURDFYQECK-UHFFFAOYSA-N 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
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- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- CKEZORGILUGFBH-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-[2-(ethylsulfinylmethyl)phenyl]methanone Chemical compound CCS(=O)CC1=CC=CC=C1C(=O)C1=C(C2CC2)ON=C1 CKEZORGILUGFBH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- JMPJSERZUVQXMR-UHFFFAOYSA-N BrC1=CC(=C(C(=O)C=2C=NOC2C2CC2)C=C1)CS(=O)C(C)(C)C Chemical compound BrC1=CC(=C(C(=O)C=2C=NOC2C2CC2)C=C1)CS(=O)C(C)(C)C JMPJSERZUVQXMR-UHFFFAOYSA-N 0.000 claims description 2
- POBDAZPEXKMUIV-UHFFFAOYSA-N BrC1=CC(=C(C(=O)C=2C=NOC2C2CC2)C=C1)CS(=O)C1=CC=CC=C1 Chemical compound BrC1=CC(=C(C(=O)C=2C=NOC2C2CC2)C=C1)CS(=O)C1=CC=CC=C1 POBDAZPEXKMUIV-UHFFFAOYSA-N 0.000 claims description 2
- YLBPQXMRUJMBCB-UHFFFAOYSA-N C(=O)C1=NOC=C1.C1=CC=CC=C1 Chemical compound C(=O)C1=NOC=C1.C1=CC=CC=C1 YLBPQXMRUJMBCB-UHFFFAOYSA-N 0.000 claims description 2
- QFOQKSKCWBOUAJ-UHFFFAOYSA-N ClC1=C(C(=C(C(=O)C=2C=NOC2C2CC2)C=C1)S(=O)C)CS(=O)CC Chemical compound ClC1=C(C(=C(C(=O)C=2C=NOC2C2CC2)C=C1)S(=O)C)CS(=O)CC QFOQKSKCWBOUAJ-UHFFFAOYSA-N 0.000 claims description 2
- RWLJAMMZDUQYDP-UHFFFAOYSA-N ClC1=C(C(=O)C=2C=NOC2C2CC2)C=CC(=C1CS(=O)C)S(=O)C Chemical compound ClC1=C(C(=O)C=2C=NOC2C2CC2)C=CC(=C1CS(=O)C)S(=O)C RWLJAMMZDUQYDP-UHFFFAOYSA-N 0.000 claims description 2
- UCVRNXUPKCXHJL-UHFFFAOYSA-N ClC1=C(C=C(C(=O)C=2C=NOC2C2CC2)C=C1)CS(=O)C Chemical compound ClC1=C(C=C(C(=O)C=2C=NOC2C2CC2)C=C1)CS(=O)C UCVRNXUPKCXHJL-UHFFFAOYSA-N 0.000 claims description 2
- NDFCKRLPFYVVJW-UHFFFAOYSA-N [2-(benzenesulfonylmethyl)-4-bromophenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound C=1C=CC=CC=1S(=O)(=O)CC1=CC(Br)=CC=C1C(=O)C=1C=NOC=1C1CC1 NDFCKRLPFYVVJW-UHFFFAOYSA-N 0.000 claims description 2
- JKOBDHYLVWIYPE-UHFFFAOYSA-N [4-bromo-2-(ethylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CCS(=O)CC1=CC(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 JKOBDHYLVWIYPE-UHFFFAOYSA-N 0.000 claims description 2
- ITKADROZLAHODH-UHFFFAOYSA-N [4-bromo-2-(prop-1-enylsulfinylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CC=CS(=O)CC1=CC(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 ITKADROZLAHODH-UHFFFAOYSA-N 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 1
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- 125000004434 sulfur atom Chemical group 0.000 claims 1
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- 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 abstract 1
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- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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- 230000008025 crystallization Effects 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000010908 decantation Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- UXOLDCOJRAMLTQ-UHFFFAOYSA-N ethyl 2-chloro-2-hydroxyiminoacetate Chemical compound CCOC(=O)C(Cl)=NO UXOLDCOJRAMLTQ-UHFFFAOYSA-N 0.000 description 1
- PZWBBVLRCWNTDT-UHFFFAOYSA-N ethyl 3-amino-4-chlorobenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(N)=C1 PZWBBVLRCWNTDT-UHFFFAOYSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 159000000003 magnesium salts Chemical class 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- SGFACFBLUAWICV-UHFFFAOYSA-N methyl 4-bromo-2-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1CBr SGFACFBLUAWICV-UHFFFAOYSA-N 0.000 description 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- RHUHXMPSKUCNKR-UHFFFAOYSA-N tert-butyl 3-cyclopropyl-3-oxopropanoate;magnesium Chemical compound [Mg].CC(C)(C)OC(=O)CC(=O)C1CC1 RHUHXMPSKUCNKR-UHFFFAOYSA-N 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 150000003568 thioethers Chemical class 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
- 150000003613 toluenes Chemical class 0.000 description 1
- 229950004288 tosilate Drugs 0.000 description 1
- 230000009466 transformation Effects 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- 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)
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939302049A GB9302049D0 (en) | 1993-02-03 | 1993-02-03 | Compositions of new matter |
| GB9302049 | 1993-02-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1091739A CN1091739A (zh) | 1994-09-07 |
| CN1039229C true CN1039229C (zh) | 1998-07-22 |
Family
ID=10729728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94101760A Expired - Fee Related CN1039229C (zh) | 1993-02-03 | 1994-02-03 | 4-苯甲酰异噁唑衍生物及其除草剂组合物和制备方法 |
Country Status (36)
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9302072D0 (en) * | 1993-02-03 | 1993-03-24 | Rhone Poulenc Agriculture | New compositions of matter |
| AU1758595A (en) * | 1994-02-25 | 1995-09-11 | Rhone-Poulenc Agrochimie | Pesticidal method |
| US5552367A (en) * | 1994-11-18 | 1996-09-03 | Rhone-Poulenc Agriculture Ltd. | Synergistic herbicidal compositions comprising 4-benzoylisoxazole and dinitroaniline herbicides |
| US5627131A (en) * | 1995-01-09 | 1997-05-06 | Zeneca Limited | Herbicidal compositions of 4-benzoylisoxazole and antidotes therefor |
| CA2213078A1 (en) * | 1995-02-15 | 1996-08-22 | Kazufumi Nakamura | Isoxazole derivatives |
| ZA9610348B (en) * | 1995-12-20 | 1997-07-11 | Rhone Poulenc Agriculture | Herbicidal compositions |
| ES2163729T3 (es) | 1996-02-01 | 2002-02-01 | Aventis Cropscience Sa | Procedimiento para preparar compuestos dicetonicos. |
| GB9603127D0 (en) * | 1996-02-15 | 1996-04-17 | Rhone Poulenc Agriculture | New process for preparing intermediates |
| CN1211241A (zh) * | 1996-02-16 | 1999-03-17 | 罗纳-普朗克农业公司 | 制备杀虫剂的新颖的中间体 |
| DE19614858A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide heterocyclisch substituierte Benzoylisothiazole |
| DE19614856A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide heterocyclisch anellierte 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 |
| US20030041357A1 (en) * | 1996-11-07 | 2003-02-27 | Zeneca Limited | Herbicide resistant plants |
| 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 |
| US6069115A (en) * | 1997-11-12 | 2000-05-30 | Rhone-Poulenc Agrochimie | Method of controlling weeds in transgenic crops |
| CN1597672A (zh) | 1998-07-24 | 2005-03-23 | 拜尔公司 | 取代的苯甲酰基环己二酮类化合物 |
| 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 |
| DE19920791A1 (de) * | 1999-05-06 | 2000-11-09 | Bayer Ag | Substituierte Benzoylisoxazole |
| DE19946853A1 (de) | 1999-09-30 | 2001-04-05 | Bayer Ag | Substituierte Arylketone |
| CN1509285A (zh) * | 2000-01-17 | 2004-06-30 | 被取代的芳基酮类 | |
| DE10037149A1 (de) * | 2000-07-29 | 2002-02-07 | Bayer Ag | Substituierte Arylketone |
| US6545185B1 (en) | 2001-03-29 | 2003-04-08 | Eagleview Technologies, Inc. | Preparation of ketones from aldehydes |
| DE10136449A1 (de) * | 2001-05-09 | 2002-11-14 | Bayer Ag | Substituierte Arylketone |
| WO2002090336A1 (de) * | 2001-05-09 | 2002-11-14 | Bayer Cropscience Ag | Substituierte arylketone |
| DE10206792A1 (de) | 2002-02-19 | 2003-08-28 | Bayer Cropscience Ag | Substituierte Arylketone |
| DE10209645A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Ag | Substituierte Arylketone |
| DE10341534A1 (de) * | 2003-09-09 | 2005-03-31 | Bayer Chemicals Ag | Difluoralkylaromaten |
| US8899502B2 (en) | 2007-04-05 | 2014-12-02 | Metso Minerals Inc. | Crusher and control method for a crusher |
| WO2013124230A1 (de) | 2012-02-21 | 2013-08-29 | Bayer Intellectual Property Gmbh | Herbizid wirksame sulfinimidoyl- und sulfonimidoylbenzoylderivate |
| US9580398B2 (en) | 2012-04-02 | 2017-02-28 | The Trustees Of Columbia University In The City Of New York | Compounds, compositions, and methods for modulating ferroptosis and treating excitotoxic disorders |
| RU2538601C2 (ru) * | 2012-12-20 | 2015-01-10 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Способ получения [n-(трет-бутилсульфанилметил)-бензиланилин щавелевокислый] сульфата меди пентагидрата и его применение в качестве водорастворимого средства для борьбы с почвенной и поверхностно-семенной инфекцией |
| US12492173B2 (en) | 2019-01-14 | 2025-12-09 | Bayer Aktiengesellschaft | Herbicidal substituted N-tetrazolyl aryl carboxamides |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1050188A (zh) * | 1989-09-11 | 1991-03-27 | 罗纳-普朗克农业化学公司 | 异唑除草剂 |
| CN1058777A (zh) * | 1990-08-10 | 1992-02-19 | 罗纳-普朗克农业有限公司 | 异唑衍生物 |
| CN1061596A (zh) * | 1990-11-22 | 1992-06-03 | 罗纳-普朗克农业有限公司 | 4-苯甲酰异唑衍生物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL102674A (en) * | 1991-08-05 | 1996-11-14 | Rhone Poulenc Agriculture | 4-Benzoyl isoxazole derivatives process for their preparation and herbicidal compositions containing them |
| GB9116834D0 (en) * | 1991-08-05 | 1991-09-18 | Rhone Poulenc Agriculture | Compositions of new matter |
-
1993
- 1993-02-03 GB GB939302049A patent/GB9302049D0/en active Pending
-
1994
- 1994-01-21 ZA ZA94451A patent/ZA94451B/xx unknown
- 1994-01-26 PH PH47666A patent/PH30125A/en unknown
- 1994-01-27 IL IL108451A patent/IL108451A/en not_active IP Right Cessation
- 1994-01-28 BR BR9400234A patent/BR9400234A/pt not_active IP Right Cessation
- 1994-01-31 AT AT94101365T patent/ATE225338T1/de not_active IP Right Cessation
- 1994-01-31 EP EP94101365A patent/EP0609798B1/en not_active Expired - Lifetime
- 1994-01-31 ES ES94101365T patent/ES2180549T3/es not_active Expired - Lifetime
- 1994-01-31 VN VNS-689/94A patent/VN279A1/vi unknown
- 1994-01-31 DE DE69431450T patent/DE69431450T2/de not_active Expired - Fee Related
- 1994-01-31 MY MYPI94000240A patent/MY110536A/en unknown
- 1994-01-31 DK DK94101365T patent/DK0609798T3/da active
- 1994-02-01 HR HR9302049.3A patent/HRP940054A2/xx not_active Application Discontinuation
- 1994-02-01 EG EG6394A patent/EG20523A/xx active
- 1994-02-01 RU RU94002996A patent/RU2124505C1/ru not_active IP Right Cessation
- 1994-02-01 SK SK107-94A patent/SK281356B6/sk unknown
- 1994-02-01 CZ CZ1994220A patent/CZ287416B6/cs not_active IP Right Cessation
- 1994-02-01 MA MA23408A patent/MA23102A1/fr unknown
- 1994-02-01 CA CA002114696A patent/CA2114696C/en not_active Expired - Fee Related
- 1994-02-02 RO RO94-00158A patent/RO112725B1/ro unknown
- 1994-02-02 TR TR00085/94A patent/TR27580A/xx unknown
- 1994-02-02 YU YU5294A patent/YU5294A/sh unknown
- 1994-02-02 PL PL94302119A patent/PL178627B1/pl not_active IP Right Cessation
- 1994-02-02 ZW ZW1094A patent/ZW1094A1/xx unknown
- 1994-02-02 KR KR1019940001904A patent/KR100313724B1/ko not_active Expired - Fee Related
- 1994-02-02 HU HU9400298A patent/HU214159B/hu not_active IP Right Cessation
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1050188A (zh) * | 1989-09-11 | 1991-03-27 | 罗纳-普朗克农业化学公司 | 异唑除草剂 |
| CN1058777A (zh) * | 1990-08-10 | 1992-02-19 | 罗纳-普朗克农业有限公司 | 异唑衍生物 |
| CN1061596A (zh) * | 1990-11-22 | 1992-06-03 | 罗纳-普朗克农业有限公司 | 4-苯甲酰异唑衍生物 |
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