HRP950137A2 - New sulfonylureas - Google Patents

New sulfonylureas Download PDF

Info

Publication number: HRP950137A2
Authority: HR; Croatia
Prior art keywords: formula; alkyl; methyl; compounds; image
Prior art date: 1991-01-25

Application number

HRP-60/92A

Other languages

English (en)

Croatian (hr)

Original Assignee

Ciba Geigy Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-01-25

Filing date

1995-03-23

Publication date

1997-08-31

1992-01-20 Priority claimed from YU6092A external-priority patent/YU6092A/sh

1995-03-23 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1997-08-31 Publication of HRP950137A2 publication Critical patent/HRP950137A2/hr

Links

229940100389 Sulfonylurea Drugs 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 57
239000000126 substance Substances 0.000 claims description 55
-1 methoxy, ethoxy Chemical group 0.000 claims description 52
241000196324 Embryophyta Species 0.000 claims description 34
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
238000000034 method Methods 0.000 claims description 24
239000000460 chlorine Substances 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
229910052801 chlorine Inorganic materials 0.000 claims description 21
229910052760 oxygen Inorganic materials 0.000 claims description 19
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
239000011737 fluorine Substances 0.000 claims description 18
229910052731 fluorine Inorganic materials 0.000 claims description 18
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
239000004202 carbamide Substances 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
230000008635 plant growth Effects 0.000 claims description 11
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 8
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
239000011593 sulfur Substances 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 6
239000005864 Sulphur Substances 0.000 claims description 6
239000013543 active substance Substances 0.000 claims description 6
230000008859 change Effects 0.000 claims description 6
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
XBXHEDNNWSJZPK-UHFFFAOYSA-N chlorosulfonyloxybenzene Chemical class ClS(=O)(=O)OC1=CC=CC=C1 XBXHEDNNWSJZPK-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 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 compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
101100054666 Streptomyces halstedii sch3 gene Chemical group 0.000 claims description 3
239000004009 herbicide Substances 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
244000045561 useful plants Species 0.000 claims description 3
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
229910003204 NH2 Inorganic materials 0.000 claims description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000006011 chloroethoxy group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 2
YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 claims description 2
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims 1
235000019256 formaldehyde Nutrition 0.000 claims 1
239000012948 isocyanate Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000843 powder Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
230000002363 herbicidal effect Effects 0.000 description 10
230000000694 effects Effects 0.000 description 9
239000008187 granular material Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
239000004094 surface-active agent Substances 0.000 description 8
239000000839 emulsion Substances 0.000 description 7
238000002386 leaching Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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 6
238000001704 evaporation Methods 0.000 description 6
238000009472 formulation Methods 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000005507 spraying Methods 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
235000013877 carbamide Nutrition 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
230000001105 regulatory effect Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
239000005457 ice water Substances 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
FGXMGZDXXPFRPN-UHFFFAOYSA-N oxetan-3-yl 2-sulfamoylbenzoate Chemical compound NS(=O)(=O)C1=CC=CC=C1C(=O)OC1COC1 FGXMGZDXXPFRPN-UHFFFAOYSA-N 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000002689 soil Substances 0.000 description 4
238000009331 sowing Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
BSGLKJAXBCHKOQ-UHFFFAOYSA-N 2-propan-2-ylbenzenecarbothioic s-acid Chemical compound CC(C)C1=CC=CC=C1C(O)=S BSGLKJAXBCHKOQ-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000001931 aliphatic group Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000000969 carrier Substances 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000006378 damage Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
230000035784 germination Effects 0.000 description 3
230000012010 growth Effects 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
150000004679 hydroxides Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000002736 nonionic surfactant Substances 0.000 description 3
OHAXOTJFANLXGC-UHFFFAOYSA-N oxetan-3-yl 2-chlorosulfonyloxybenzoate Chemical compound ClS(=O)(=O)OC1=CC=CC=C1C(=O)OC1COC1 OHAXOTJFANLXGC-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
238000012545 processing Methods 0.000 description 3
238000002791 soaking Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000004546 suspension concentrate Substances 0.000 description 3
230000009105 vegetative growth Effects 0.000 description 3
FQVVJFIHGLIEBJ-UHFFFAOYSA-N 2-chlorosulfonylbenzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1S(Cl)(=O)=O FQVVJFIHGLIEBJ-UHFFFAOYSA-N 0.000 description 2
HLUGXOQWZICRTA-UHFFFAOYSA-N 2-propan-2-ylbenzenecarbothioyl chloride Chemical compound CC(C)C1=CC=CC=C1C(Cl)=S HLUGXOQWZICRTA-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
240000002791 Brassica napus Species 0.000 description 2
235000006008 Brassica napus var napus Nutrition 0.000 description 2
229910021532 Calcite Inorganic materials 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
235000019484 Rapeseed oil Nutrition 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
230000000274 adsorptive effect Effects 0.000 description 2
230000009418 agronomic effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000012237 artificial material Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000003240 coconut oil Substances 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
238000007865 diluting Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000010410 dusting Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
235000019197 fats Nutrition 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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 2
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150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000003672 ureas Chemical class 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
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Indole Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Saccharide Compounds (AREA)

HRP-60/92A 1991-01-25 1995-03-23 New sulfonylureas HRP950137A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH22091		1991-01-25
YU6092A YU6092A (sh)	1992-01-20	1992-01-20	Novi sulfonilkarbamidi

Publications (1)

Publication Number	Publication Date
HRP950137A2 true HRP950137A2 (en)	1997-08-31

Family

ID=4182017

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HRP-60/92A HRP950137A2 (en)	1991-01-25	1995-03-23	New sulfonylureas

Country Status (39)

Country	Link
US (4)	US5209771A (no)
EP (1)	EP0496701B1 (no)
JP (1)	JPH04346983A (no)
KR (1)	KR920014807A (no)
CN (1)	CN1039771C (no)
AP (1)	AP296A (no)
AT (1)	ATE135004T1 (no)
AU (2)	AU645389B2 (no)
BG (1)	BG61187B1 (no)
BR (1)	BR9200213A (no)
CA (1)	CA2059882C (no)
CZ (1)	CZ279595B6 (no)
DE (1)	DE59205530D1 (no)
DK (1)	DK0496701T3 (no)
EE (1)	EE02947B1 (no)
EG (1)	EG19684A (no)
ES (1)	ES2084975T3 (no)
FI (1)	FI920279A (no)
GR (1)	GR3019245T3 (no)
HR (1)	HRP950137A2 (no)
HU (1)	HUT60603A (no)
IE (1)	IE71042B1 (no)
IL (3)	IL100741A (no)
LT (1)	LT3731B (no)
LV (1)	LV10610B (no)
MA (1)	MA22399A1 (no)
MD (1)	MD707C2 (no)
MX (1)	MX9200273A (no)
NO (1)	NO179251C (no)
NZ (1)	NZ241385A (no)
PL (2)	PL169554B1 (no)
RO (1)	RO106991B1 (no)
RU (1)	RU2056415C1 (no)
SI (1)	SI9210060A (no)
SK (1)	SK278536B6 (no)
TN (1)	TNSN92005A1 (no)
TR (1)	TR25726A (no)
UY (1)	UY23364A1 (no)
ZA (1)	ZA92503B (no)

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US5519148A (en) *	1991-01-25	1996-05-21	Ciba-Geigy Corporation	Sulfonylureas
EP0496701B1 (de) *	1991-01-25	1996-03-06	Ciba-Geigy Ag	Sulfonylharnstoffe als Herbizide
WO1993017015A1 (en)	1992-02-21	1993-09-02	Ciba-Geigy Ag	Sulfonylureas as herbicides
CA2128325A1 (en) *	1992-02-21	1993-09-02	Beat Jau	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
EP0746514B1 (en)	1994-02-24	1999-04-14	Novartis AG	Process for the fabrication of a container for chemicals
AU3387395A (en) *	1994-09-06	1996-03-29	Novartis Ag	Herbicidal synergistic composition and method of weed conrol
CA2199604C (en) *	1994-09-13	2002-03-05	Donald J. Townsend	Continuous chewing gum manufacturing from base concentrate
BR9606948A (pt) *	1995-02-13	1997-12-23	Novartis Ag Novartis S A Novar	Composições herbicida e método de controle de plantas daninhas
EP0751136B1 (de) *	1995-06-29	1999-12-29	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
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
PL217234B1 (pl)	1998-08-13	2014-06-30	Bayer Cropscience Ag	Zastosowanie kompozycji herbicydów zawierającej glufosynat i sulkotrion lub mezotrion do zwalczania szkodliwych roślin w uprawach kukurydzy, sposób zwalczania szkodliwych roślin w uprawach kukurydzy oraz kompozycja herbicydów
WO2003082008A1 (fr) *	2002-03-29	2003-10-09	Kumiai Chemical Industry Co., Ltd.	Composition agrochimique granulaire
EP2052606A1 (de)	2007-10-24	2009-04-29	Bayer CropScience AG	Herbizid-Kombination
DE102008037620A1 (de)	2008-08-14	2010-02-18	Bayer Crop Science Ag	Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden
CN103220911B (zh)	2010-10-15	2017-02-15	拜耳知识产权有限责任公司	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
EA029716B1 (ru)	2011-05-04	2018-05-31	Байер Интеллектчуал Проперти Гмбх	Применение гербицидов ингибиторов als для борьбы с нежелательными растениями среди растений brassica, таких как b. napus, толерантных к гербицидам ингибиторов als
WO2014090760A1 (en)	2012-12-13	2014-06-19	Bayer Cropscience Ag	Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants
MD1088Z (ro) *	2016-04-13	2017-06-30	Институт Генетики, Физиологии И Защиты Растений Академии Наук Молдовы	Procedeu de cultivare a plantelor de cultură
CN118201483A (zh)	2021-10-15	2024-06-14	科沃施种子欧洲股份两合公司	ALS抑制剂除草剂耐受的甜菜(Beta Vulgaris)突变体

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ATE32892T1 (de) *	1982-08-23	1988-03-15	Ciba Geigy Ag	Verfahren zur herstellung von herbiziden und pflanzenwuchsregulierenden sulfonylharnstoffen.
EP0126711B1 (de)	1983-05-16	1989-08-02	Ciba-Geigy Ag	Herbizid wirksame und pflanzenwuchsregulierende Pyrimidin-Derivate, deren Herstellung und Verwendung
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US5084082A (en) *	1988-09-22	1992-01-28	E. I. Du Pont De Nemours And Company	Soybean plants with dominant selectable trait for herbicide resistance
JP2598317B2 (ja) *	1989-02-08	1997-04-09	呉羽化学工業株式会社	Ｎ‐置換‐３‐（含窒素５員環）ベンゼンスルホンアミド誘導体、その製造方法及び除草剤
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EP0496701B1 (de) *	1991-01-25	1996-03-06	Ciba-Geigy Ag	Sulfonylharnstoffe als Herbizide

1992
- 1992-01-16 EP EP92810027A patent/EP0496701B1/de not_active Expired - Lifetime
- 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 AT AT92810027T patent/ATE135004T1/de not_active IP Right Cessation
- 1992-01-16 DE DE59205530T patent/DE59205530D1/de not_active Expired - Fee Related
- 1992-01-20 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/FI920279A/fi unknown
- 1992-01-22 MX MX9200273A patent/MX9200273A/es not_active IP Right Cessation
- 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 AU AU10432/92A patent/AU645389B2/en not_active Ceased
- 1992-01-23 NZ NZ241385A patent/NZ241385A/xx unknown
- 1992-01-23 CA CA002059882A patent/CA2059882C/en not_active Expired - Lifetime
- 1992-01-23 KR KR1019920000923A patent/KR920014807A/ko not_active Application Discontinuation
- 1992-01-24 MA MA22685A patent/MA22399A1/fr unknown
- 1992-01-24 HU HU9200237A patent/HUT60603A/hu unknown
- 1992-01-24 PL PL92293282A patent/PL169554B1/pl unknown
- 1992-01-24 IE IE920224A patent/IE71042B1/en not_active IP Right Cessation
- 1992-01-24 PL PL92296107A patent/PL169407B1/pl unknown
- 1992-01-24 RO RO9200013A patent/RO106991B1/ro unknown
- 1992-01-24 SK SK215-92A patent/SK278536B6/sk unknown
- 1992-01-24 TN TNTNSN92005A patent/TNSN92005A1/fr unknown
- 1992-01-24 RU SU925010749A patent/RU2056415C1/ru active
- 1992-01-24 ZA ZA92503A patent/ZA92503B/xx unknown
- 1992-01-24 TR TR92/0071A patent/TR25726A/xx unknown
- 1992-01-24 JP JP4034412A patent/JPH04346983A/ja active Pending
- 1992-01-24 NO NO920328A patent/NO179251C/no unknown
- 1992-01-24 BG BG95816A patent/BG61187B1/bg unknown
- 1992-01-24 CZ CS92215A patent/CZ279595B6/cs unknown
- 1992-01-24 AP APAP/P/1992/000351A patent/AP296A/en active
- 1992-01-24 CN CN92100442A patent/CN1039771C/zh not_active Expired - Lifetime
- 1992-01-27 UY UY23364A patent/UY23364A1/es unknown
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
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
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

Also Published As

Publication number	Publication date
MD707B2 (en)	1997-04-30
IL100741A (en)	1996-10-16
MA22399A1 (fr)	1992-10-01
PL169554B1 (pl)	1996-08-30
BG95816A (en)	1994-06-30
FI920279A (fi)	1992-07-26
DK0496701T3 (da)	1996-04-01
NO920328L (no)	1992-07-27
BR9200213A (pt)	1992-10-06
LV10610B (en)	1996-04-20
IE71042B1 (en)	1997-01-15
GR3019245T3 (en)	1996-06-30
SI9210060A (en)	1994-06-30
ATE135004T1 (de)	1996-03-15
NZ241385A (en)	1993-03-26
PL296107A1 (en)	1993-05-31
US5412107A (en)	1995-05-02
MX9200273A (es)	1992-07-01
ES2084975T3 (es)	1996-05-16
AP296A (en)	1994-01-14
PL169407B1 (pl)	1996-07-31
KR920014807A (ko)	1992-08-25
RU2056415C1 (ru)	1996-03-20
AU653480B2 (en)	1994-09-29
NO179251B (no)	1996-05-28
PL293282A1 (no)	1993-02-08
CA2059882C (en)	2005-10-25
IE920224A1 (en)	1992-07-29
EP0496701B1 (de)	1996-03-06
US5597779A (en)	1997-01-28
LTIP1655A (en)	1995-07-25
AU1043292A (en)	1992-07-30
BG61187B1 (bg)	1997-02-28
EE02947B1 (et)	1996-12-16
LV10610A (lv)	1995-04-20
US5286709A (en)	1994-02-15
IL100741A0 (en)	1992-09-06
TNSN92005A1 (fr)	1993-06-08
HUT60603A (en)	1992-10-28
IL116253A0 (en)	1996-03-31
CN1063490A (zh)	1992-08-12
LT3731B (en)	1996-02-26
RO106991B1 (ro)	1993-08-30
ZA92503B (en)	1992-11-25
CA2059882A1 (en)	1992-07-26
AP9200351A0 (en)	1992-01-31
EG19684A (en)	1995-09-30
NO179251C (no)	1996-09-04
SK278536B6 (en)	1997-09-10
DE59205530D1 (de)	1996-04-11
HU9200237D0 (en)	1992-05-28
UY23364A1 (es)	1992-06-16
EP0496701A1 (de)	1992-07-29
AU645389B2 (en)	1994-01-13
TR25726A (tr)	1993-09-01
US5209771A (en)	1993-05-11
CN1039771C (zh)	1998-09-16
JPH04346983A (ja)	1992-12-02
NO920328D0 (no)	1992-01-24
CS21592A3 (en)	1992-08-12
CZ279595B6 (cs)	1995-05-17
IL116254A0 (en)	1996-03-31
MD940282A (en)	1996-10-31
AU5513794A (en)	1994-04-14
FI920279A0 (fi)	1992-01-22
MD707C2 (ro)	1998-02-28

Legal Events

Date	Code	Title	Description
1997-08-31	A1OB	Publication of a patent application
1997-09-30	PPPP	Transfer of rights	Owner name: NOVARTIS AKTIENGESELLSCHAFT, CH
1998-04-16	ODBC	Application rejected

Publication	Publication Date	Title
HRP950137A2 (en)	1997-08-31	New sulfonylureas
US4940482A (en)	1990-07-10	Aminopyrazinones and aminotriazinones of the formula
CA1229086A (en)	1987-11-10	Herbicidal halopyrimidines
US5336773A (en)	1994-08-09	Certain-3-amino-2-pyridine-sulfonamide intermediates
JPH0656827A (ja)	1994-03-01	新規のスルホニル尿素
NO176714B (no)	1995-02-06	Herbicide [[(1,3,5-triazin-2-yl)aminokarbonylÅ-aminosulfonylÅbenzosyreestere og herbicid middel, og anvendelse av disse
AU634239B2 (en)	1993-02-18	N-pyridinesulfonyl-n'-pyrimidinyl-(triazin-yl-) ureas and herbicidal and plant growth regulating compositions containing the same
LT3236B (en)	1995-04-25	Novel sulfonylcarbamides
US5552368A (en)	1996-09-03	Sulfonylureas
AU627946B2 (en)	1992-09-03	Sulfamidosulfonylurea derivatives
LT3020B (lt)	1994-08-25	Nauji sulfonilkarbamidai