LV10610B - Sulfonilurea derivatives, process for preparing thereof, intermediates, herbicidal agent and means containing sulfonilurea for prevent of plant growing, struggle method against weed - Google Patents
Sulfonilurea derivatives, process for preparing thereof, intermediates, herbicidal agent and means containing sulfonilurea for prevent of plant growing, struggle method against weed Download PDFInfo
- Publication number
- LV10610B LV10610B LVP-93-413A LV930413A LV10610B LV 10610 B LV10610 B LV 10610B LV 930413 A LV930413 A LV 930413A LV 10610 B LV10610 B LV 10610B
- Authority
- LV
- Latvia
- Prior art keywords
- anspruch
- alkyl
- formel
- methyl
- och3
- Prior art date
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- 241000196324 Embryophyta Species 0.000 title claims description 10
- 239000004009 herbicide Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 2
- GQSFASWYVBMKSL-UHFFFAOYSA-N 1-methyl-3-methylsulfonylurea Chemical class CNC(=O)NS(C)(=O)=O GQSFASWYVBMKSL-UHFFFAOYSA-N 0.000 title 2
- 239000000543 intermediate Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 C 1 -C 4 -Alkoxy Chemical group 0.000 claims description 67
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 14
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical group CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- XBXHEDNNWSJZPK-UHFFFAOYSA-N chlorosulfonyloxybenzene Chemical compound ClS(=O)(=O)OC1=CC=CC=C1 XBXHEDNNWSJZPK-UHFFFAOYSA-N 0.000 claims description 4
- WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical compound OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 claims description 4
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical group [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 3
- SBUKLPSBNFWJCU-UHFFFAOYSA-N ClIBr Chemical compound ClIBr SBUKLPSBNFWJCU-UHFFFAOYSA-N 0.000 claims description 3
- 240000005979 Hordeum vulgare Species 0.000 claims description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- RRLXFVUQHVOUOT-UHFFFAOYSA-N 4-isocyanatotriazine Chemical compound O=C=NC1=CC=NN=N1 RRLXFVUQHVOUOT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 claims description 2
- FHIDNBAQOFJWCA-UAKXSSHOSA-N 5-fluorouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 FHIDNBAQOFJWCA-UAKXSSHOSA-N 0.000 claims 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- UJTMLNARSPORHR-UHFFFAOYSA-N oc2h5 Chemical compound C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 235000012054 meals Nutrition 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 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 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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- 229910052708 sodium Inorganic materials 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 206010013786 Dry skin Diseases 0.000 description 3
- 206010018612 Gonorrhoea Diseases 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 208000001786 gonorrhea Diseases 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- FGXMGZDXXPFRPN-UHFFFAOYSA-N oxetan-3-yl 2-sulfamoylbenzoate Chemical class NS(=O)(=O)C1=CC=CC=C1C(=O)OC1COC1 FGXMGZDXXPFRPN-UHFFFAOYSA-N 0.000 description 3
- 238000010422 painting Methods 0.000 description 3
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- 239000011591 potassium Substances 0.000 description 3
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- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- GABQKHQNXWNJJJ-UHFFFAOYSA-N diphenylcarbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)C1=CC=CC=C1 GABQKHQNXWNJJJ-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
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- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical compound CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical compound CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
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- RDWBWBOPAWKJAZ-UHFFFAOYSA-N n-(ethylamino)-n-(methylamino)propan-1-amine Chemical compound CCCN(NC)NCC RDWBWBOPAWKJAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- QMLWSAXEQSBAAQ-UHFFFAOYSA-N oxetan-3-ol Chemical compound OC1COC1 QMLWSAXEQSBAAQ-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-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
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 102200108034 rs41311087 Human genes 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- XEQVFTJINCDKEW-UHFFFAOYSA-N thietan-2-yl 2-chlorosulfonyloxybenzoate Chemical compound ClS(=O)(=O)OC1=CC=CC=C1C(=O)OC1SCC1 XEQVFTJINCDKEW-UHFFFAOYSA-N 0.000 description 1
- FXUIDSNQABZUQQ-UHFFFAOYSA-N thietan-2-yl 2-sulfamoylbenzoate Chemical compound NS(=O)(=O)C1=CC=CC=C1C(=O)OC1SCC1 FXUIDSNQABZUQQ-UHFFFAOYSA-N 0.000 description 1
- MZULBPRXGFCDQL-UHFFFAOYSA-N thietan-3-yl 2-chlorosulfonyloxybenzoate Chemical compound ClS(=O)(=O)OC1=CC=CC=C1C(=O)OC1CSC1 MZULBPRXGFCDQL-UHFFFAOYSA-N 0.000 description 1
- QHHVRULMESYJFF-UHFFFAOYSA-N thietan-3-yl 2-sulfamoylbenzoate Chemical compound NS(=O)(=O)C1=CC=CC=C1C(=O)OC1CSC1 QHHVRULMESYJFF-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- XSYLPIPLYOCKKP-UHFFFAOYSA-N triazin-4-ylcarbamic acid Chemical compound OC(=O)NC1=CC=NN=N1 XSYLPIPLYOCKKP-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no 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 atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/04—Four-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH22091 | 1991-01-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV10610A LV10610A (lv) | 1995-04-20 |
| LV10610B true LV10610B (en) | 1996-04-20 |
Family
ID=4182017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-93-413A LV10610B (en) | 1991-01-25 | 1993-05-25 | Sulfonilurea derivatives, process for preparing thereof, intermediates, herbicidal agent and means containing sulfonilurea for prevent of plant growing, struggle method against weed |
Country Status (39)
| Country | Link |
|---|---|
| US (4) | US5209771A (cs) |
| EP (1) | EP0496701B1 (cs) |
| JP (1) | JPH04346983A (cs) |
| KR (1) | KR920014807A (cs) |
| CN (1) | CN1039771C (cs) |
| AP (1) | AP296A (cs) |
| AT (1) | ATE135004T1 (cs) |
| AU (2) | AU645389B2 (cs) |
| BG (1) | BG61187B1 (cs) |
| BR (1) | BR9200213A (cs) |
| CA (1) | CA2059882C (cs) |
| CZ (1) | CZ279595B6 (cs) |
| DE (1) | DE59205530D1 (cs) |
| DK (1) | DK0496701T3 (cs) |
| EE (1) | EE02947B1 (cs) |
| EG (1) | EG19684A (cs) |
| ES (1) | ES2084975T3 (cs) |
| FI (1) | FI920279A7 (cs) |
| GR (1) | GR3019245T3 (cs) |
| HR (1) | HRP950137A2 (cs) |
| HU (1) | HUT60603A (cs) |
| IE (1) | IE71042B1 (cs) |
| IL (3) | IL100741A (cs) |
| LT (1) | LT3731B (cs) |
| LV (1) | LV10610B (cs) |
| MA (1) | MA22399A1 (cs) |
| MD (1) | MD707C2 (cs) |
| MX (1) | MX9200273A (cs) |
| NO (1) | NO179251C (cs) |
| NZ (1) | NZ241385A (cs) |
| PL (2) | PL169554B1 (cs) |
| RO (1) | RO106991B1 (cs) |
| RU (1) | RU2056415C1 (cs) |
| SI (1) | SI9210060A (cs) |
| SK (1) | SK278536B6 (cs) |
| TN (1) | TNSN92005A1 (cs) |
| TR (1) | TR25726A (cs) |
| UY (1) | UY23364A1 (cs) |
| ZA (1) | ZA92503B (cs) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5489695A (en) * | 1991-01-25 | 1996-02-06 | Ciba-Geigy Corporation | Sulfonylureas |
| ATE135004T1 (de) * | 1991-01-25 | 1996-03-15 | Ciba Geigy Ag | Sulfonylharnstoffe als herbizide |
| AU3496493A (en) * | 1992-02-21 | 1993-09-13 | Ciba-Geigy Ag | Sulfonylureas as herbicides |
| WO1993017015A1 (en) | 1992-02-21 | 1993-09-02 | Ciba-Geigy Ag | Sulfonylureas as herbicides |
| MY109136A (en) * | 1992-07-30 | 1996-12-31 | Ciba Geigy Ag | Selective herbicidal composition |
| EE9400262A (et) * | 1993-12-08 | 1996-02-15 | Ciba-Geigy Ag | Selektiivne herbitsiidsegu ja selle kasutamise meetod |
| AU1757095A (en) | 1994-02-24 | 1995-09-11 | Ciba-Geigy Ag | Container for chemicals |
| WO1996008146A2 (en) * | 1994-09-06 | 1996-03-21 | Novartis Ag | Herbicidal synergistic composition and method of weed control |
| PL319143A1 (en) * | 1994-09-13 | 1997-07-21 | Wrigley W M Jun Co | Continuous method of making chewing gum from the chewing gum base concentrate |
| DE69606855D1 (de) * | 1995-02-13 | 2000-04-06 | Novartis Ag | Herbizide zusammensetzung und verfahren zur bekämpfung und unkräutern |
| DE59604010D1 (de) * | 1995-06-29 | 2000-02-03 | Novartis Ag | Verfahren zur Herstellung von 3-hydroxyoxetanen |
| US6586367B2 (en) | 1996-09-05 | 2003-07-01 | Syngenta Crop Protection, Inc. | Process for the control of weeds |
| EP0929543B1 (en) * | 1996-09-26 | 2001-10-31 | Syngenta Participations AG | Herbicidal composition |
| DE19702200A1 (de) | 1997-01-23 | 1998-07-30 | Hoechst Schering Agrevo Gmbh | Phenylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| DE19821614A1 (de) | 1998-05-14 | 1999-11-18 | Hoechst Schering Agrevo Gmbh | Sulfonylharnstoff-tolerante Zuckerrübenmutanten |
| DE19821613A1 (de) | 1998-05-14 | 1999-11-18 | Hoechst Schering Agrevo Gmbh | Transgene Sulfonylharnstoff-tolerante Zuckerrübenmutanten |
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| DE19836660A1 (de) | 1998-08-13 | 2000-02-17 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel für tolerante oder resistente Sojakulturen |
| DE19836659A1 (de) | 1998-08-13 | 2000-02-17 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel für tolerante oder resistente Baumwollkulturen |
| EP1498030B1 (en) * | 2002-03-29 | 2012-02-22 | Kumiai Chemical Industry Co., Ltd. | Granular agricultural-chemical composition |
| EP2052606A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| USD585914S1 (en) * | 2008-06-20 | 2009-02-03 | Illinois Tool Works Inc. | Grinder/polisher |
| DE102008037620A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| PT3284346T (pt) | 2010-10-15 | 2021-09-29 | Bayer Cropscience Ag | Utilização de herbicidas inibidores de als para controlo de vegetação indesejada em plantas de beta vulgaris tolerantes a inibidor de als |
| EP2713733B1 (en) | 2011-05-04 | 2018-03-14 | Bayer Intellectual Property GmbH | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant brassica, such as b. napus, plants |
| CN105377028B (zh) | 2012-12-13 | 2018-11-30 | 拜耳作物科学股份公司 | Als抑制剂除草剂用于在对als抑制剂除草剂耐受的甜菜植物中防治不想要的植物的用途 |
| MD1088Z (ro) * | 2016-04-13 | 2017-06-30 | Институт Генетики, Физиологии И Защиты Растений Академии Наук Молдовы | Procedeu de cultivare a plantelor de cultură |
| JP2024537389A (ja) | 2021-10-15 | 2024-10-10 | カー・ヴェー・エス ザート エス・エー ウント コー． カー・ゲー・アー・アー | Ａｌｓ阻害剤除草剤耐性ベータ・ブルガリス（ｂｅｔａ ｖｕｌｇａｒｉｓ）突然変異体 |
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| DK163123C (da) * | 1978-05-30 | 1992-06-09 | Du Pont | Benzensulfonylurinstoffer til anvendelse som herbicider eller plantevaekstregulatorer, praeparat indeholdende dem samt deres anvendelse |
| US4383113A (en) * | 1978-05-30 | 1983-05-10 | E. I. Du Pont De Nemours And Company | Agricultural sulfonamides |
| ZA806970B (en) * | 1979-11-30 | 1982-06-30 | Du Pont | Agricultural sulfonamides |
| US4892946A (en) * | 1979-11-30 | 1990-01-09 | E. I. Du Pont De Nemours And Company | Agricultural sulfonamides |
| JPS5947600B2 (ja) * | 1980-06-12 | 1984-11-20 | 旭化成株式会社 | 加工殿粉 |
| GR71993B (cs) * | 1980-11-19 | 1983-08-26 | Stavffer Chemical Company | |
| AU550945B2 (en) * | 1981-07-10 | 1986-04-10 | E.I. Du Pont De Nemours And Company | Triazolyl-(imidazolyl)-sulphonyl-ureas |
| US4579584A (en) * | 1981-10-13 | 1986-04-01 | Ciba-Geigy Corporation | N-phenylsulfonyl-N'-triazinylureas |
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| US4546179A (en) * | 1983-11-23 | 1985-10-08 | E. I. Du Pont De Nemours And Company | Process for preparing sulfonylureas |
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| DE3811777A1 (de) * | 1988-04-08 | 1989-10-19 | Hoechst Ag | Heterocyclisch substituierte alkyl- und alkenylsulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren |
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-
1992
- 1992-01-16 AT AT92810027T patent/ATE135004T1/de not_active IP Right Cessation
- 1992-01-16 DE DE59205530T patent/DE59205530D1/de not_active Expired - Fee Related
- 1992-01-16 DK DK92810027.0T patent/DK0496701T3/da not_active Application Discontinuation
- 1992-01-16 ES ES92810027T patent/ES2084975T3/es not_active Expired - Lifetime
- 1992-01-16 EP EP92810027A patent/EP0496701B1/de not_active Expired - Lifetime
- 1992-01-20 SI SI9210060A patent/SI9210060A/sl unknown
- 1992-01-21 US US07/823,515 patent/US5209771A/en not_active Expired - Lifetime
- 1992-01-21 EG EG3692A patent/EG19684A/xx active
- 1992-01-22 FI FI920279A patent/FI920279A7/fi unknown
- 1992-01-22 MX MX9200273A patent/MX9200273A/es not_active IP Right Cessation
- 1992-01-23 NZ NZ241385A patent/NZ241385A/xx unknown
- 1992-01-23 IL IL10074192A patent/IL100741A/en not_active IP Right Cessation
- 1992-01-23 BR BR929200213A patent/BR9200213A/pt not_active IP Right Cessation
- 1992-01-23 CA CA002059882A patent/CA2059882C/en not_active Expired - Lifetime
- 1992-01-23 AU AU10432/92A patent/AU645389B2/en not_active Ceased
- 1992-01-23 KR KR1019920000923A patent/KR920014807A/ko not_active Ceased
- 1992-01-24 RU SU925010749A patent/RU2056415C1/ru active
- 1992-01-24 ZA ZA92503A patent/ZA92503B/xx unknown
- 1992-01-24 RO RO9200013A patent/RO106991B1/ro unknown
- 1992-01-24 TN TNTNSN92005A patent/TNSN92005A1/fr unknown
- 1992-01-24 BG BG95816A patent/BG61187B1/bg unknown
- 1992-01-24 JP JP4034412A patent/JPH04346983A/ja active Pending
- 1992-01-24 PL PL92293282A patent/PL169554B1/pl unknown
- 1992-01-24 HU HU9200237A patent/HUT60603A/hu unknown
- 1992-01-24 TR TR92/0071A patent/TR25726A/xx unknown
- 1992-01-24 AP APAP/P/1992/000351A patent/AP296A/en active
- 1992-01-24 PL PL92296107A patent/PL169407B1/pl unknown
- 1992-01-24 IE IE920224A patent/IE71042B1/en not_active IP Right Cessation
- 1992-01-24 CN CN92100442A patent/CN1039771C/zh not_active Expired - Lifetime
- 1992-01-24 SK SK215-92A patent/SK278536B6/sk unknown
- 1992-01-24 CZ CS92215A patent/CZ279595B6/cs unknown
- 1992-01-24 NO NO920328A patent/NO179251C/no unknown
- 1992-01-24 MA MA22685A patent/MA22399A1/fr unknown
- 1992-01-27 UY UY23364A patent/UY23364A1/es unknown
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1993
- 1993-02-08 US US08/014,947 patent/US5286709A/en not_active Expired - Lifetime
- 1993-05-25 LV LVP-93-413A patent/LV10610B/lv unknown
- 1993-11-19 US US08/154,768 patent/US5412107A/en not_active Expired - Lifetime
- 1993-12-21 LT LTIP1655A patent/LT3731B/lt not_active IP Right Cessation
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1994
- 1994-02-14 AU AU55137/94A patent/AU653480B2/en not_active Ceased
- 1994-07-14 MD MD94-0282A patent/MD707C2/ro unknown
- 1994-11-17 EE EE9400402A patent/EE02947B1/xx unknown
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1995
- 1995-03-23 HR HRP-60/92A patent/HRP950137A2/hr not_active Application Discontinuation
- 1995-04-10 US US08/419,307 patent/US5597779A/en not_active Expired - Lifetime
- 1995-12-05 IL IL11625395A patent/IL116253A0/xx unknown
- 1995-12-05 IL IL11625495A patent/IL116254A0/xx unknown
-
1996
- 1996-03-07 GR GR960400509T patent/GR3019245T3/el unknown
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