JPS6245228B2 - - Google Patents
Info
- Publication number
- JPS6245228B2 JPS6245228B2 JP56112039A JP11203981A JPS6245228B2 JP S6245228 B2 JPS6245228 B2 JP S6245228B2 JP 56112039 A JP56112039 A JP 56112039A JP 11203981 A JP11203981 A JP 11203981A JP S6245228 B2 JPS6245228 B2 JP S6245228B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- compound according
- atom
- urea
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 157
- 125000004432 carbon atom Chemical group C* 0.000 claims description 150
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 45
- 125000005843 halogen group Chemical group 0.000 claims description 43
- -1 -CH2 -C( CH3 )= CH2 Chemical group 0.000 claims description 41
- 239000004202 carbamide Substances 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 40
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 125000004434 sulfur atom Chemical group 0.000 claims description 26
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 241000196324 Embryophyta Species 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 229940124530 sulfonamide Drugs 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 150000003456 sulfonamides Chemical class 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 5
- 230000008635 plant growth Effects 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 4
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- OCLNXDPSSAYYNO-UHFFFAOYSA-N 1-(4-chloro-6-methylpyrimidin-2-yl)-3-[2-(difluoromethoxy)phenyl]sulfonylurea Chemical compound CC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)F)=N1 OCLNXDPSSAYYNO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- ACDVCPLIMIGCQM-UHFFFAOYSA-N 1-(4-chloro-6-methoxypyrimidin-2-yl)-3-[2-(difluoromethylsulfanyl)phenyl]sulfonylurea Chemical compound COC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)SC(F)F)=N1 ACDVCPLIMIGCQM-UHFFFAOYSA-N 0.000 claims description 2
- YNLPNHOFFDASIQ-UHFFFAOYSA-N 1-[2-(difluoromethoxy)phenyl]sulfonyl-3-(4-ethyl-6-methoxy-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(CC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)F)=N1 YNLPNHOFFDASIQ-UHFFFAOYSA-N 0.000 claims description 2
- QQXOTCILZPQVQQ-UHFFFAOYSA-N 1-[2-(difluoromethoxy)phenyl]sulfonyl-3-(4-methoxy-6-propan-2-yloxy-1,3,5-triazin-2-yl)urea Chemical compound CC(C)OC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)F)=N1 QQXOTCILZPQVQQ-UHFFFAOYSA-N 0.000 claims description 2
- WEWISYVVLDNUQR-UHFFFAOYSA-N 1-[2-(difluoromethylsulfanyl)phenyl]sulfonyl-3-(4-ethyl-6-methoxy-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(CC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)SC(F)F)=N1 WEWISYVVLDNUQR-UHFFFAOYSA-N 0.000 claims description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 244000045561 useful plants Species 0.000 claims description 2
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims 10
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 2
- LGBFWRRYCMQYJC-UHFFFAOYSA-N 1-(2-but-2-enoxyphenyl)sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical class COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCC=CC)=N1 LGBFWRRYCMQYJC-UHFFFAOYSA-N 0.000 claims 1
- CVOKIPRTQSZLNH-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(2-methoxyethoxy)phenyl]sulfonylurea Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 CVOKIPRTQSZLNH-UHFFFAOYSA-N 0.000 claims 1
- BFPPLGLSGQOCCT-UHFFFAOYSA-N 1-(4,6-dimethylpyrimidin-2-yl)-3-[2-(1,1,2,2,2-pentafluoroethoxy)phenyl]sulfonylurea Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)(F)C(F)(F)F)=N1 BFPPLGLSGQOCCT-UHFFFAOYSA-N 0.000 claims 1
- OYKHTYUXQYUQAX-UHFFFAOYSA-N 1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(1,1,2,2,2-pentafluoroethoxy)phenyl]sulfonylurea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)(F)C(F)(F)F)=N1 OYKHTYUXQYUQAX-UHFFFAOYSA-N 0.000 claims 1
- GKBXSPVLDBMDLI-UHFFFAOYSA-N 1-(4-methoxy-6-methylpyrimidin-2-yl)-3-[2-(1,1,2,2,2-pentafluoroethoxy)phenyl]sulfonylurea Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)(F)C(F)(F)F)=N1 GKBXSPVLDBMDLI-UHFFFAOYSA-N 0.000 claims 1
- LLCWDBDYLWGHMY-UHFFFAOYSA-N 1-[2-(1,2-dichloroethenoxy)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical group ClC(=CCl)OC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=NC(=N1)OC)C LLCWDBDYLWGHMY-UHFFFAOYSA-N 0.000 claims 1
- DJMMPOAWCASTNJ-UHFFFAOYSA-N 1-[2-(2,3-dibromo-2-methylpropoxy)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCC(C)(Br)CBr)=N1 DJMMPOAWCASTNJ-UHFFFAOYSA-N 0.000 claims 1
- VENWCFBYRISXKV-UHFFFAOYSA-N 1-[2-(2-methoxyethylsulfanyl)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COCCSC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VENWCFBYRISXKV-UHFFFAOYSA-N 0.000 claims 1
- 229940100389 Sulfonylurea Drugs 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000004480 active ingredient Substances 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000004094 surface-active agent Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000012141 concentrate Substances 0.000 description 11
- 235000008504 concentrate Nutrition 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 7
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 230000035784 germination Effects 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000004009 herbicide Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 244000061456 Solanum tuberosum Species 0.000 description 5
- 235000002595 Solanum tuberosum Nutrition 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 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 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 235000012015 potatoes Nutrition 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XDODAVQVIOWLPT-UHFFFAOYSA-N 2-(difluoromethoxy)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1OC(F)F XDODAVQVIOWLPT-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- ZSMAHBFDTZQZRQ-UHFFFAOYSA-N 2-(1,1,2,2,2-pentafluoroethoxy)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1OC(F)(F)C(F)(F)F ZSMAHBFDTZQZRQ-UHFFFAOYSA-N 0.000 description 3
- XYYNESSXKACQSR-UHFFFAOYSA-N 2-(1,1,2,2,2-pentafluoroethoxy)benzenesulfonyl chloride Chemical compound FC(F)(F)C(F)(F)OC1=CC=CC=C1S(Cl)(=O)=O XYYNESSXKACQSR-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MOXDGMSQFFMNHA-UHFFFAOYSA-N 2-hydroxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1O MOXDGMSQFFMNHA-UHFFFAOYSA-N 0.000 description 3
- KAVPSXHBCUWGHT-UHFFFAOYSA-N 2-prop-2-enoxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1OCC=C KAVPSXHBCUWGHT-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
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 3
- 239000005648 plant growth regulator Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- MZCYFEMRFUAIAD-UHFFFAOYSA-N 1-(4,6-dichloro-1,3,5-triazin-2-yl)-1-[2-(difluoromethoxy)phenyl]sulfonylurea Chemical compound C=1C=CC=C(OC(F)F)C=1S(=O)(=O)N(C(=O)N)C1=NC(Cl)=NC(Cl)=N1 MZCYFEMRFUAIAD-UHFFFAOYSA-N 0.000 description 2
- UJJQRJPAQKUPAQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-pyrimidin-2-ylurea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC1=NC=CC=N1 UJJQRJPAQKUPAQ-UHFFFAOYSA-N 0.000 description 2
- KKLCXLMBJIGEER-UHFFFAOYSA-N 1-[2-(2-chloroethylsulfanyl)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)SCCCl)=N1 KKLCXLMBJIGEER-UHFFFAOYSA-N 0.000 description 2
- XIAQGIIHTOTNCU-UHFFFAOYSA-N 1-methyl-3-[2-(1,1,2,2,2-pentafluoroethoxy)phenyl]sulfonylurea Chemical compound CNC(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)(F)C(F)(F)F XIAQGIIHTOTNCU-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- CSAHXQVUVOUPEY-UHFFFAOYSA-N 2-(difluoromethoxy)benzenesulfonyl chloride Chemical compound FC(F)OC1=CC=CC=C1S(Cl)(=O)=O CSAHXQVUVOUPEY-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229910021532 Calcite Inorganic materials 0.000 description 2
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- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 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 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical class [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- SMJBOENAPOXLRZ-UHFFFAOYSA-N n-(oxomethylidene)-2-(1,1,2,2,2-pentafluoroethoxy)benzenesulfonamide Chemical compound FC(F)(F)C(F)(F)OC1=CC=CC=C1S(=O)(=O)N=C=O SMJBOENAPOXLRZ-UHFFFAOYSA-N 0.000 description 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002373 plant growth inhibitor Substances 0.000 description 1
- 239000003123 plant toxin Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000004162 soil erosion Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000003760 tallow Substances 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
- GNWGXASUBJBGGD-UHFFFAOYSA-N triazin-4-ylurea Chemical compound NC(=O)NC1=CC=NN=N1 GNWGXASUBJBGGD-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5481/80A CH657849A5 (en) | 1980-07-17 | 1980-07-17 | N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinyl ureas |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5756452A JPS5756452A (en) | 1982-04-05 |
| JPS6245228B2 true JPS6245228B2 (nl) | 1987-09-25 |
Family
ID=4294310
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56112039A Granted JPS5756452A (en) | 1980-07-17 | 1981-07-17 | N-phenylsulfonyl-n'-pyrimidinyl- and -triazinylurea, manufacture and plant growth regulant composition |
| JP61214981A Granted JPS62116554A (ja) | 1980-07-17 | 1986-09-11 | フエニルスルホンアミド |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61214981A Granted JPS62116554A (ja) | 1980-07-17 | 1986-09-11 | フエニルスルホンアミド |
Country Status (10)
| Country | Link |
|---|---|
| JP (2) | JPS5756452A (nl) |
| AU (1) | AU570734B2 (nl) |
| CH (1) | CH657849A5 (nl) |
| HU (1) | HU191006B (nl) |
| LT (1) | LT2601B (nl) |
| LV (1) | LV5156A3 (nl) |
| MD (1) | MD39C2 (nl) |
| MX (1) | MX5719A (nl) |
| SU (1) | SU1289390A3 (nl) |
| ZA (1) | ZA814874B (nl) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1221698A (en) * | 1981-12-07 | 1987-05-12 | Rafael Shapiro | N-arylsulfonyl-n'-pyrimidinyl and triazinylureas |
| US4521597A (en) * | 1982-10-25 | 1985-06-04 | Ciba Geigy Corporation | Process for producing sulfonylureas having a herbicidal action |
| DE3472881D1 (de) * | 1983-03-28 | 1988-09-01 | Ciba Geigy Ag | N-phenylsulfonyl-n'-pyrimidinyl- and -triazinyl urea |
| JPS6038372A (ja) * | 1983-07-18 | 1985-02-27 | チバガイギー アクチエンゲゼルシヤフト | スルフオニル尿素の製造方法 |
| DD238318A5 (de) * | 1984-08-30 | 1986-08-20 | Bayer Ag,De | Herbizide mittel |
| US4898973A (en) * | 1985-03-07 | 1990-02-06 | Ici Americas Inc. | Trisubstituted benzoic acid intermediates |
| USH386H (en) | 1985-08-27 | 1987-12-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CA1230119A (en) | 1985-11-22 | 1987-12-08 | Craig L. Hillemann | N-2-carboxylphenylsulfonyl-n'-pyrimidin-2-yl or triazin-2-yl-urea compounds |
| JP4952819B2 (ja) * | 2010-04-27 | 2012-06-13 | 井関農機株式会社 | 脱穀機 |
| JP4952855B2 (ja) * | 2011-05-30 | 2012-06-13 | 井関農機株式会社 | 脱穀機 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52122384A (en) * | 1976-04-07 | 1977-10-14 | Du Pont | Nn*heterocyclic aminocarbonyl*aryl sulfonamide and agricultural chemicals containing same |
| JPS5636467A (en) * | 1979-07-26 | 1981-04-09 | Du Pont | Herbicidal sulfonamides and their application |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4190432A (en) * | 1977-08-01 | 1980-02-26 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4141916A (en) * | 1978-02-13 | 1979-02-27 | The Dow Chemical Company | 3,4,5-Trichloro-N,N-Di(loweralkyl)-2-((chloromethyl)thio)benzenesulfonamides |
| US4452628A (en) * | 1979-07-26 | 1984-06-05 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
-
1980
- 1980-07-17 CH CH5481/80A patent/CH657849A5/de not_active IP Right Cessation
-
1981
- 1981-07-16 HU HU812083A patent/HU191006B/hu unknown
- 1981-07-16 ZA ZA814874A patent/ZA814874B/xx unknown
- 1981-07-16 SU SU813308965A patent/SU1289390A3/ru active
- 1981-07-17 JP JP56112039A patent/JPS5756452A/ja active Granted
-
1984
- 1984-10-12 AU AU34217/84A patent/AU570734B2/en not_active Expired
-
1985
- 1985-10-01 MX MX571985A patent/MX5719A/es unknown
-
1986
- 1986-09-11 JP JP61214981A patent/JPS62116554A/ja active Granted
-
1993
- 1993-06-11 LV LV930557A patent/LV5156A3/xx unknown
- 1993-09-29 LT LTRP1271A patent/LT2601B/xx not_active IP Right Cessation
-
1994
- 1994-03-24 MD MD94-0064A patent/MD39C2/ro unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52122384A (en) * | 1976-04-07 | 1977-10-14 | Du Pont | Nn*heterocyclic aminocarbonyl*aryl sulfonamide and agricultural chemicals containing same |
| JPS5636467A (en) * | 1979-07-26 | 1981-04-09 | Du Pont | Herbicidal sulfonamides and their application |
Also Published As
| Publication number | Publication date |
|---|---|
| CH657849A5 (en) | 1986-09-30 |
| MD39B1 (ro) | 1994-08-31 |
| JPS62116554A (ja) | 1987-05-28 |
| ZA814874B (en) | 1982-08-25 |
| JPH0214347B2 (nl) | 1990-04-06 |
| HU191006B (en) | 1986-12-28 |
| LT2601B (lt) | 1994-03-25 |
| AU570734B2 (en) | 1988-03-24 |
| LV5156A3 (lv) | 1993-10-10 |
| SU1289390A3 (ru) | 1987-02-07 |
| JPS5756452A (en) | 1982-04-05 |
| MD39C2 (ro) | 1995-03-31 |
| AU3421784A (en) | 1985-02-07 |
| MX5719A (es) | 1993-09-01 |
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