CA1040208A - Herbicidal n-(3-cyano-4-alkylthien-2-yl) ureas - Google Patents
Herbicidal n-(3-cyano-4-alkylthien-2-yl) ureasInfo
- Publication number
- CA1040208A CA1040208A CA220,886A CA220886A CA1040208A CA 1040208 A CA1040208 A CA 1040208A CA 220886 A CA220886 A CA 220886A CA 1040208 A CA1040208 A CA 1040208A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- alkyl
- cyano
- hydrogen
- compound
- 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
- 235000013877 carbamide Nutrition 0.000 title abstract description 11
- 150000003672 ureas Chemical class 0.000 title abstract 2
- 230000002363 herbicidal effect Effects 0.000 title description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- XWBAWKNCMUSFJH-UHFFFAOYSA-N 1-(4-butan-2-yl-3-cyanothiophen-2-yl)-3-methylurea Chemical compound CCC(C)C1=CSC(NC(=O)NC)=C1C#N XWBAWKNCMUSFJH-UHFFFAOYSA-N 0.000 claims description 2
- WKUHLXNZPPDNMN-UHFFFAOYSA-N 1-(3-cyano-4-propan-2-ylthiophen-2-yl)-3-methylurea Chemical compound CNC(=O)NC=1SC=C(C(C)C)C=1C#N WKUHLXNZPPDNMN-UHFFFAOYSA-N 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 17
- -1 thienyl ureas Chemical class 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000000370 acceptor Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HWZFIQWMNSJQCE-UHFFFAOYSA-N 4-tert-butyl-5-chlorothiophene-3-carbonitrile Chemical compound CC(C)(C)C1=C(Cl)SC=C1C#N HWZFIQWMNSJQCE-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- XSBUXOHYKAAGDQ-UHFFFAOYSA-N 1-(4-tert-butyl-3-cyanothiophen-2-yl)-3-methylurea Chemical compound CNC(=O)NC=1SC=C(C(C)(C)C)C=1C#N XSBUXOHYKAAGDQ-UHFFFAOYSA-N 0.000 description 1
- FQFUFWGVLXLVHV-UHFFFAOYSA-N 1-(4-tert-butyl-5-chloro-3-cyanothiophen-2-yl)-3-methylurea Chemical compound CNC(=O)NC=1SC(Cl)=C(C(C)(C)C)C=1C#N FQFUFWGVLXLVHV-UHFFFAOYSA-N 0.000 description 1
- NBGFGYXYMAHCID-UHFFFAOYSA-N 2-(1-cyclopropylethylidene)propanedinitrile Chemical group N#CC(C#N)=C(C)C1CC1 NBGFGYXYMAHCID-UHFFFAOYSA-N 0.000 description 1
- QPIHYNPMFIKQRM-UHFFFAOYSA-N 2-amino-4-butan-2-ylthiophene-3-carbonitrile Chemical compound CCC(C)C1=CSC(N)=C1C#N QPIHYNPMFIKQRM-UHFFFAOYSA-N 0.000 description 1
- GCJLGWPBKQCVNF-UHFFFAOYSA-N 2-amino-4-cyclopropylthiophene-3-carbonitrile Chemical compound N#CC1=C(N)SC=C1C1CC1 GCJLGWPBKQCVNF-UHFFFAOYSA-N 0.000 description 1
- HLCATPHPMNURNM-UHFFFAOYSA-N 2-amino-4-tert-butylthiophene-3-carbonitrile Chemical compound CC(C)(C)C1=CSC(N)=C1C#N HLCATPHPMNURNM-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- FHRWDLIGUYTBHR-UHFFFAOYSA-N 3-(4-tert-butyl-3-cyanothiophen-2-yl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC=1SC=C(C(C)(C)C)C=1C#N FHRWDLIGUYTBHR-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- LZDPZKBVRTYUMQ-UHFFFAOYSA-N 3-tert-butylthiophene Chemical compound CC(C)(C)C=1C=CSC=1 LZDPZKBVRTYUMQ-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000404 calcium aluminium silicate Substances 0.000 description 1
- 235000012215 calcium aluminium silicate Nutrition 0.000 description 1
- WNCYAPRTYDMSFP-UHFFFAOYSA-N calcium aluminosilicate Chemical compound [Al+3].[Al+3].[Ca+2].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O WNCYAPRTYDMSFP-UHFFFAOYSA-N 0.000 description 1
- 229940078583 calcium aluminosilicate Drugs 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229940083608 sodium hydroxide Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/453,231 US3956315A (en) | 1974-03-21 | 1974-03-21 | Herbicidal N-(3-cyano-4-alkylthien-2-yl) ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1040208A true CA1040208A (en) | 1978-10-10 |
Family
ID=23799705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA220,886A Expired CA1040208A (en) | 1974-03-21 | 1975-02-27 | Herbicidal n-(3-cyano-4-alkylthien-2-yl) ureas |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3956315A (https=) |
| JP (1) | JPS50154427A (https=) |
| CA (1) | CA1040208A (https=) |
| DE (1) | DE2510936A1 (https=) |
| FR (1) | FR2264814B1 (https=) |
| GB (1) | GB1462570A (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2619861C2 (de) * | 1976-05-03 | 1985-05-09 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1-(2-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-harnstoff sowie diesen enthaltende Mittel zur Wachstumsregulierung und zur Entlbätterung von Pflanzen |
| DE2817449A1 (de) * | 1978-04-21 | 1979-10-31 | Bayer Ag | Mittel zur regulierung des pflanzenwachstums |
| DE3529247A1 (de) * | 1985-05-17 | 1986-11-20 | Bayer Ag, 5090 Leverkusen | Verwendung von thienylharnstoffen und -isoharnstoffen als leistungsfoerdernde mittel bei tieren, neue thienylharnstoffe und -isoharnstoffe und ihre herstellung |
| DE3541628A1 (de) * | 1985-11-26 | 1987-05-27 | Bayer Ag | Thienylharnstoff-derivate |
| EP0273602A1 (en) * | 1986-12-05 | 1988-07-06 | Eli Lilly And Company | 3-Cyano-4-arylthiophenes |
| DE4039734A1 (de) * | 1990-12-13 | 1992-06-17 | Basf Ag | Substituierte 2-aminothiophene enthaltende herbizide mittel |
| US20020002199A1 (en) * | 1998-03-12 | 2002-01-03 | Lone Jeppesen | Modulators of protein tyrosine phosphatases (ptpases) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3326663A (en) * | 1964-09-25 | 1967-06-20 | Shell Oil Co | Herbicidal phenylureas |
| BE754782A (fr) * | 1969-08-14 | 1971-02-12 | May & Baker Ltd | Derives du thiophene a action herbicide |
| FR2084629A5 (en) * | 1970-03-16 | 1971-12-17 | Shell Int Research | Herbicidal thiophenes - eg amide, urea and carbamate derivs |
-
1974
- 1974-03-21 US US05/453,231 patent/US3956315A/en not_active Expired - Lifetime
-
1975
- 1975-02-27 CA CA220,886A patent/CA1040208A/en not_active Expired
- 1975-03-13 DE DE19752510936 patent/DE2510936A1/de not_active Withdrawn
- 1975-03-13 FR FR7507935A patent/FR2264814B1/fr not_active Expired
- 1975-03-20 JP JP50055557A patent/JPS50154427A/ja active Pending
- 1975-03-21 GB GB1203775A patent/GB1462570A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2510936A1 (de) | 1975-10-09 |
| FR2264814A1 (https=) | 1975-10-17 |
| JPS50154427A (https=) | 1975-12-12 |
| GB1462570A (en) | 1977-01-26 |
| FR2264814B1 (https=) | 1979-06-08 |
| US3956315A (en) | 1976-05-11 |
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