RU2124505C1 - Производное 4-бензоилизоксазола или его приемлемая для сельского хозяйства соль, гербицидная композиция и способ борьбы с сорняками - Google Patents
Производное 4-бензоилизоксазола или его приемлемая для сельского хозяйства соль, гербицидная композиция и способ борьбы с сорняками Download PDFInfo
- Publication number
- RU2124505C1 RU2124505C1 RU94002996A RU94002996A RU2124505C1 RU 2124505 C1 RU2124505 C1 RU 2124505C1 RU 94002996 A RU94002996 A RU 94002996A RU 94002996 A RU94002996 A RU 94002996A RU 2124505 C1 RU2124505 C1 RU 2124505C1
- Authority
- RU
- Russia
- Prior art keywords
- benzoyl
- cyclopropylisoxazole
- bromo
- cyclopropyl
- isoxazole
- Prior art date
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- 241000196324 Embryophyta Species 0.000 title claims abstract description 53
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 33
- 150000003839 salts Chemical class 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 16
- 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 15
- 239000000203 mixture Substances 0.000 title claims description 97
- 239000004009 herbicide Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 132
- 125000005843 halogen group Chemical group 0.000 claims abstract description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- -1 [2,4-dichloro-3- (methylsulfonylmethyl) benzoyl] isoxazole Chemical compound 0.000 claims description 33
- 239000003085 diluting agent Substances 0.000 claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 14
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 239000012141 concentrate Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 239000008187 granular material Substances 0.000 claims description 7
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- SIMACDMCZBJRHO-UHFFFAOYSA-N [4-bromo-2-(methylsulfonylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)(=O)CC1=CC(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 SIMACDMCZBJRHO-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- SZDKGSQKOZBBSL-UHFFFAOYSA-N [4-bromo-2-(methylsulfanylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CSCC1=CC(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 SZDKGSQKOZBBSL-UHFFFAOYSA-N 0.000 claims description 4
- 239000004550 soluble concentrate Substances 0.000 claims description 4
- BVMBBJJZGDJOIO-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-[3,4-dichloro-2-(methylsulfonylmethyl)phenyl]methanone Chemical compound CS(=O)(=O)CC1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 BVMBBJJZGDJOIO-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- ZFWQNMRTYJXQQW-UHFFFAOYSA-N [3-chloro-4-methylsulfanyl-2-(methylsulfanylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CSCC1=C(Cl)C(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 ZFWQNMRTYJXQQW-UHFFFAOYSA-N 0.000 claims description 3
- FEDKTIYCLWZBCV-UHFFFAOYSA-N [3-chloro-4-methylsulfonyl-2-(methylsulfonylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)(=O)CC1=C(Cl)C(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 FEDKTIYCLWZBCV-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- BFINATOFIPGXQG-UHFFFAOYSA-N [4-chloro-2-methoxy-3-(methylsulfonylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound COC1=C(CS(C)(=O)=O)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 BFINATOFIPGXQG-UHFFFAOYSA-N 0.000 claims description 3
- NKSQGFUGEKUDSL-UHFFFAOYSA-N [4-chloro-2-methylsulfanyl-3-(methylsulfanylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CSCC1=C(Cl)C=CC(C(=O)C2=C(ON=C2)C2CC2)=C1SC NKSQGFUGEKUDSL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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- USNASDSPDDYDOL-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-[2-(ethylsulfonylmethyl)phenyl]methanone Chemical compound CCS(=O)(=O)CC1=CC=CC=C1C(=O)C1=C(C2CC2)ON=C1 USNASDSPDDYDOL-UHFFFAOYSA-N 0.000 claims description 2
- GJJSWPAKRBZOBD-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-[2-(methylsulfanylmethyl)-4-(trifluoromethyl)phenyl]methanone Chemical compound CSCC1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 GJJSWPAKRBZOBD-UHFFFAOYSA-N 0.000 claims description 2
- BELPKTFWNFMPCF-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-[2-(methylsulfanylmethyl)phenyl]methanone Chemical compound CSCC1=CC=CC=C1C(=O)C1=C(C2CC2)ON=C1 BELPKTFWNFMPCF-UHFFFAOYSA-N 0.000 claims description 2
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- QIZBANYXVZFBJN-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-[2-fluoro-4-(methylsulfanylmethyl)phenyl]methanone Chemical compound FC1=CC(CSC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 QIZBANYXVZFBJN-UHFFFAOYSA-N 0.000 claims description 2
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- IOZWDNCMKVUSPG-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-[4-methylsulfanyl-2-(methylsulfanylmethyl)phenyl]methanone Chemical compound CSCC1=CC(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 IOZWDNCMKVUSPG-UHFFFAOYSA-N 0.000 claims description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
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- JAIMMEZJDFKGOR-UHFFFAOYSA-N [2-chloro-4-(methylsulfonylmethyl)phenyl]-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound ClC1=CC(CS(=O)(=O)C)=CC=C1C(=O)C1=C(C2CC2)ON=C1 JAIMMEZJDFKGOR-UHFFFAOYSA-N 0.000 claims description 2
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- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
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- 239000003513 alkali Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
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- 125000003118 aryl group Chemical group 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
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
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- 238000005260 corrosion Methods 0.000 description 1
- 244000038559 crop plants Species 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
- 238000006114 decarboxylation reaction Methods 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
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- UXOLDCOJRAMLTQ-ZZXKWVIFSA-N ethyl (2e)-2-chloro-2-hydroxyiminoacetate Chemical compound CCOC(=O)C(\Cl)=N/O UXOLDCOJRAMLTQ-ZZXKWVIFSA-N 0.000 description 1
- WTEQINJFCLXCAE-UHFFFAOYSA-N ethyl 2,4-dichloro-3-methylsulfanylbenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(SC)=C1Cl WTEQINJFCLXCAE-UHFFFAOYSA-N 0.000 description 1
- UWJIPHNMKAWAEJ-UHFFFAOYSA-N ethyl 2-(bromomethyl)-3,4-dichlorobenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(Cl)=C1CBr UWJIPHNMKAWAEJ-UHFFFAOYSA-N 0.000 description 1
- QGFBNJIOZBYJNZ-UHFFFAOYSA-N ethyl 2-chloro-4-methylsulfanyl-3-(methylsulfanylmethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(SC)C(CSC)=C1Cl QGFBNJIOZBYJNZ-UHFFFAOYSA-N 0.000 description 1
- FCMORLMTGFYBMJ-UHFFFAOYSA-N ethyl 3,4-dichloro-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(Cl)=C1C FCMORLMTGFYBMJ-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
- ISZDEZLLBGJTTF-UHFFFAOYSA-N ethyl 3-bromo-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC(Br)=C1C ISZDEZLLBGJTTF-UHFFFAOYSA-N 0.000 description 1
- WKOFEYJLYIZHEI-UHFFFAOYSA-N ethyl 3-bromo-4-chloro-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(Br)=C1C WKOFEYJLYIZHEI-UHFFFAOYSA-N 0.000 description 1
- PCVXGKLHVDJCRW-UHFFFAOYSA-N ethyl 4-[4-bromo-2-(methylsulfonylmethyl)benzoyl]-5-cyclopropyl-1,2-oxazole-3-carboxylate Chemical compound C=1C=C(Br)C=C(CS(C)(=O)=O)C=1C(=O)C=1C(C(=O)OCC)=NOC=1C1CC1 PCVXGKLHVDJCRW-UHFFFAOYSA-N 0.000 description 1
- UKXAOTFMEODWMU-UHFFFAOYSA-N ethyl 4-chloro-3-methylsulfanyl-2-(methylsulfanylmethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(SC)=C1CSC UKXAOTFMEODWMU-UHFFFAOYSA-N 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical class CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 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
- BPQPBEVHMFRECG-UHFFFAOYSA-N fluoro formate Chemical compound FOC=O BPQPBEVHMFRECG-UHFFFAOYSA-N 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000003993 interaction 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 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
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- 238000006263 metalation reaction Methods 0.000 description 1
- YZDSJOYLKATLSR-UHFFFAOYSA-N methyl 2,4-bis(methylsulfanyl)benzoate Chemical compound COC(=O)C1=CC=C(SC)C=C1SC YZDSJOYLKATLSR-UHFFFAOYSA-N 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
- FXUCZTPNPZEZID-UHFFFAOYSA-N methyl 2-fluoro-4-(methylsulfanylmethyl)benzoate Chemical compound COC(=O)C1=CC=C(CSC)C=C1F FXUCZTPNPZEZID-UHFFFAOYSA-N 0.000 description 1
- VECDHZFZAGCNDL-UHFFFAOYSA-N methyl 2-fluoro-4-methylsulfanylbenzoate Chemical compound COC(=O)C1=CC=C(SC)C=C1F VECDHZFZAGCNDL-UHFFFAOYSA-N 0.000 description 1
- OHJKSLDVIIEODM-UHFFFAOYSA-N methyl 4-bromo-2-(phenylsulfanylmethyl)benzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1CSC1=CC=CC=C1 OHJKSLDVIIEODM-UHFFFAOYSA-N 0.000 description 1
- OPSJXXIGPVSDKH-UHFFFAOYSA-N methyl 4-bromo-2-(prop-2-enylsulfanylmethyl)benzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1CSCC=C OPSJXXIGPVSDKH-UHFFFAOYSA-N 0.000 description 1
- NMOXESSENNEUBL-UHFFFAOYSA-N methyl 4-bromo-2-(tert-butylsulfanylmethyl)benzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1CSC(C)(C)C NMOXESSENNEUBL-UHFFFAOYSA-N 0.000 description 1
- GMMUSDPTZLAPTI-UHFFFAOYSA-N methyl 4-chloro-2-fluoro-3-(methylsulfanylmethyl)benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(CSC)=C1F GMMUSDPTZLAPTI-UHFFFAOYSA-N 0.000 description 1
- DGLWBZVTOAUIGP-UHFFFAOYSA-N methyl 4-chloro-2-methoxy-3-(methylsulfanylmethyl)benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(CSC)=C1OC DGLWBZVTOAUIGP-UHFFFAOYSA-N 0.000 description 1
- KATQQXZAUWKHNH-UHFFFAOYSA-N methyl 4-chloro-3-(ethylsulfanylmethyl)-2-fluorobenzoate Chemical compound CCSCC1=C(Cl)C=CC(C(=O)OC)=C1F KATQQXZAUWKHNH-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
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- 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
- 150000002823 nitrates Chemical class 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
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- 235000020232 peanut Nutrition 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
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- 235000021317 phosphate Nutrition 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
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- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- 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
- 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
- 238000012360 testing method Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 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
- 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
- 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
- 239000004552 water soluble powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
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 |
| GB932049 | 1993-02-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU94002996A RU94002996A (ru) | 1995-09-27 |
| RU2124505C1 true RU2124505C1 (ru) | 1999-01-10 |
Family
ID=10729728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU94002996A RU2124505C1 (ru) | 1993-02-03 | 1994-02-01 | Производное 4-бензоилизоксазола или его приемлемая для сельского хозяйства соль, гербицидная композиция и способ борьбы с сорняками |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (34)
| 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 |
| AU4634096A (en) * | 1995-02-15 | 1996-09-04 | Idemitsu Kosan Co. Ltd | Isoxazole derivatives |
| ZA9610348B (en) * | 1995-12-20 | 1997-07-11 | Rhone Poulenc Agriculture | Herbicidal compositions |
| PT880498E (pt) | 1996-02-01 | 2002-05-31 | Aventis Cropscience Sa | Processo para a preparacao de compostos dicetonicos |
| GB9603127D0 (en) * | 1996-02-15 | 1996-04-17 | Rhone Poulenc Agriculture | New process for preparing intermediates |
| AU722612B2 (en) * | 1996-02-16 | 2000-08-10 | Rhone-Poulenc Agro | New intermediates to pesticides |
| 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 |
| US6924251B1 (en) | 1998-07-24 | 2005-08-02 | Bayer Aktiengesellschaft | Substituted benzoylcyclohexandiones |
| US6369276B1 (en) | 1998-11-19 | 2002-04-09 | Eagleview Technologies, Inc. | Catalyst structure for ketone production and method of making and using the same |
| US6392099B1 (en) | 1998-11-19 | 2002-05-21 | Eagleview Technologies, Inc. | Method and apparatus for the preparation of ketones |
| DE19920791A1 (de) | 1999-05-06 | 2000-11-09 | Bayer Ag | Substituierte Benzoylisoxazole |
| DE19946853A1 (de) | 1999-09-30 | 2001-04-05 | Bayer Ag | Substituierte Arylketone |
| MXPA02006966A (es) * | 2000-01-17 | 2003-01-28 | Bayer Ag | Arilcetonas substituidas. |
| 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 |
| MXPA03010120A (es) * | 2001-05-09 | 2004-03-10 | Bayer Cropscience Ag | Arilcetonas substituidas. |
| 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 |
| JP5283020B2 (ja) | 2007-04-05 | 2013-09-04 | メッツオ ミネラルズ インク． | 破砕機の制御方法、破砕機及びコンピュータソフトウェア製品 |
| CN104244713B (zh) | 2012-02-21 | 2016-08-24 | 拜耳知识产权有限责任公司 | 除草的亚磺酰亚氨酰基苯甲酰基衍生物和磺酰亚氨酰基苯甲酰基衍生物 |
| 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 |
| UA128004C2 (uk) | 2019-01-14 | 2024-03-06 | Байєр Акцієнгезелльшафт | Гербіцидні заміщені n-тетразоліл-арилкарбоксаміди |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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
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1994
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- 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 ES ES94101365T patent/ES2180549T3/es not_active Expired - Lifetime
- 1994-01-31 EP EP94101365A patent/EP0609798B1/en not_active Expired - Lifetime
- 1994-01-31 DK DK94101365T patent/DK0609798T3/da active
- 1994-01-31 MY MYPI94000240A patent/MY110536A/en unknown
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- 1994-01-31 DE DE69431450T patent/DE69431450T2/de not_active Expired - Fee Related
- 1994-01-31 AT AT94101365T patent/ATE225338T1/de not_active IP Right Cessation
- 1994-02-01 EG EG6394A patent/EG20523A/xx active
- 1994-02-01 CA CA002114696A patent/CA2114696C/en not_active Expired - Fee Related
- 1994-02-01 MA MA23408A patent/MA23102A1/fr unknown
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- 1994-02-01 CZ CZ1994220A patent/CZ287416B6/cs not_active IP Right Cessation
- 1994-02-01 RU RU94002996A patent/RU2124505C1/ru not_active IP Right Cessation
- 1994-02-01 HR HR9302049.3A patent/HRP940054A2/xx not_active Application Discontinuation
- 1994-02-02 HU HU9400298A patent/HU214159B/hu not_active IP Right Cessation
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- 1994-02-02 AU AU54861/94A patent/AU670155B2/en not_active Ceased
- 1994-02-02 KR KR1019940001904A patent/KR100313724B1/ko not_active Expired - Fee Related
- 1994-02-02 RO RO94-00158A patent/RO112725B1/ro unknown
- 1994-02-02 BG BG98436A patent/BG62207B1/bg unknown
- 1994-02-02 YU YU5294A patent/YU5294A/sh unknown
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- 1994-02-02 PL PL94302119A patent/PL178627B1/pl not_active IP Right Cessation
- 1994-02-02 NZ NZ250806A patent/NZ250806A/en unknown
- 1994-02-03 AP APAP/P/1994/000617A patent/AP432A/en active
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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