GB1577523A - Herbicidally active 2-dimethylcarbamoylimino-1,3,4-thiadiazolin-3-ide derivatives process for their manufacture and their use - Google Patents
Herbicidally active 2-dimethylcarbamoylimino-1,3,4-thiadiazolin-3-ide derivatives process for their manufacture and their use Download PDFInfo
- Publication number
- GB1577523A GB1577523A GB7192/77A GB719277A GB1577523A GB 1577523 A GB1577523 A GB 1577523A GB 7192/77 A GB7192/77 A GB 7192/77A GB 719277 A GB719277 A GB 719277A GB 1577523 A GB1577523 A GB 1577523A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiadiazolin
- ide
- dimethylcarbamoylimino
- salt
- 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
- 238000000034 method Methods 0.000 title claims description 35
- IDAFAPNAZCWRKV-UHFFFAOYSA-N 1,1-dimethyl-3-(1,3,4-thiadiazol-2-yl)urea Chemical class CN(C)C(=O)NC1=NN=CS1 IDAFAPNAZCWRKV-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 76
- -1 dimethylcarbamoylimino Chemical group 0.000 claims description 58
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 41
- 229910003002 lithium salt Inorganic materials 0.000 claims description 37
- 159000000000 sodium salts Chemical class 0.000 claims description 34
- 159000000002 lithium salts Chemical class 0.000 claims description 33
- 241000196324 Embryophyta Species 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 20
- 230000002363 herbicidal effect Effects 0.000 claims description 17
- 239000004009 herbicide Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000002736 metal compounds Chemical class 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 239000002699 waste material Substances 0.000 claims description 5
- ZXARPZDAWRAOIT-UHFFFAOYSA-N 1,1-dimethyl-3-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CN(C)C(=O)NC1=NN=C(S(C)(=O)=O)S1 ZXARPZDAWRAOIT-UHFFFAOYSA-N 0.000 claims description 4
- GARHMFKENWNGGC-UHFFFAOYSA-N 3-(5-ethylsulfanyl-1,3,4-thiadiazol-2-yl)-1,1-dimethylurea Chemical compound CCSC1=NN=C(S1)NC(=O)N(C)C GARHMFKENWNGGC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- VKRGLHLCUMMXHA-UHFFFAOYSA-N 2,3-dihydro-1,3,4-thiadiazole Chemical compound C1NN=CS1 VKRGLHLCUMMXHA-UHFFFAOYSA-N 0.000 claims description 2
- PNWXIVHAFKHCRF-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylic acid Chemical compound CN(C(=O)N=C1SC=NN1C(=O)O)C PNWXIVHAFKHCRF-UHFFFAOYSA-N 0.000 claims description 2
- 235000003276 Apios tuberosa Nutrition 0.000 claims description 2
- 244000105624 Arachis hypogaea Species 0.000 claims description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
- 235000010744 Arachis villosulicarpa Nutrition 0.000 claims description 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- 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 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 241001300479 Macroptilium Species 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 235000010582 Pisum sativum Nutrition 0.000 claims description 2
- 240000004713 Pisum sativum Species 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 244000061456 Solanum tuberosum Species 0.000 claims description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
- 240000006394 Sorghum bicolor Species 0.000 claims description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 235000009973 maize Nutrition 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- PFXWXVDBAIXSCP-UHFFFAOYSA-N 1,1-dimethyl-3-(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CSC1=NN=C(NC(=O)N(C)C)S1 PFXWXVDBAIXSCP-UHFFFAOYSA-N 0.000 claims 3
- FKHOIGLKVUJMSA-UHFFFAOYSA-N 1,1-dimethyl-3-(5-pentylsulfanyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CCCCCSC1=NN=C(S1)NC(=O)N(C)C FKHOIGLKVUJMSA-UHFFFAOYSA-N 0.000 claims 3
- WJKMBNBLMLYDRS-UHFFFAOYSA-N 1,1-dimethyl-3-(5-pentylsulfinyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CCCCCS(=O)C1=NN=C(S1)NC(=O)N(C)C WJKMBNBLMLYDRS-UHFFFAOYSA-N 0.000 claims 3
- GKELLKGKUGXTIY-UHFFFAOYSA-N 1,1-dimethyl-3-(5-pentylsulfonyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CCCCCS(=O)(=O)C1=NN=C(S1)NC(=O)N(C)C GKELLKGKUGXTIY-UHFFFAOYSA-N 0.000 claims 3
- DCTHZADHZXFSSS-UHFFFAOYSA-N 1,1-dimethyl-3-(5-propan-2-ylsulfanyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CC(C)SC1=NN=C(S1)NC(=O)N(C)C DCTHZADHZXFSSS-UHFFFAOYSA-N 0.000 claims 3
- KGXGTRIYWGCMGQ-UHFFFAOYSA-N 1,1-dimethyl-3-(5-propan-2-ylsulfinyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CC(C)S(=O)C1=NN=C(S1)NC(=O)N(C)C KGXGTRIYWGCMGQ-UHFFFAOYSA-N 0.000 claims 3
- GYGUPMMMTFPKGW-UHFFFAOYSA-N 1,1-dimethyl-3-(5-propan-2-ylsulfonyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CC(C)S(=O)(=O)C1=NN=C(S1)NC(=O)N(C)C GYGUPMMMTFPKGW-UHFFFAOYSA-N 0.000 claims 3
- HNNGQWJQWDCSIV-UHFFFAOYSA-N 1,1-dimethyl-3-(5-propylsulfanyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CCCSC1=NN=C(S1)NC(=O)N(C)C HNNGQWJQWDCSIV-UHFFFAOYSA-N 0.000 claims 3
- OVDAJFNZJYIWKB-UHFFFAOYSA-N 1,1-dimethyl-3-(5-propylsulfonyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CCCS(=O)(=O)C1=NN=C(S1)NC(=O)N(C)C OVDAJFNZJYIWKB-UHFFFAOYSA-N 0.000 claims 3
- UKWPBNKWVRGHAJ-UHFFFAOYSA-N 1,1-dimethyl-3-[5-(2-methylpropylsulfanyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CC(C)CSC1=NN=C(S1)NC(=O)N(C)C UKWPBNKWVRGHAJ-UHFFFAOYSA-N 0.000 claims 3
- PBXMVTYKTFMWOE-UHFFFAOYSA-N 1,1-dimethyl-3-[5-(2-methylpropylsulfinyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CC(C)CS(=O)C1=NN=C(S1)NC(=O)N(C)C PBXMVTYKTFMWOE-UHFFFAOYSA-N 0.000 claims 3
- DHBDEBJACXPFOV-UHFFFAOYSA-N 1,1-dimethyl-3-[5-(2-methylpropylsulfonyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CC(C)CS(=O)(=O)C1=NN=C(S1)NC(=O)N(C)C DHBDEBJACXPFOV-UHFFFAOYSA-N 0.000 claims 3
- SGDWLBRFQSYURG-UHFFFAOYSA-N 3-(5-butylsulfanyl-1,3,4-thiadiazol-2-yl)-1,1-dimethylurea Chemical compound CCCCSC1=NN=C(S1)NC(=O)N(C)C SGDWLBRFQSYURG-UHFFFAOYSA-N 0.000 claims 3
- YACFYZZDFYGUJS-UHFFFAOYSA-N 3-(5-hexylsulfanyl-1,3,4-thiadiazol-2-yl)-1,1-dimethylurea Chemical compound CCCCCCSC1=NN=C(S1)NC(=O)N(C)C YACFYZZDFYGUJS-UHFFFAOYSA-N 0.000 claims 3
- UELVORNTLCQNFH-UHFFFAOYSA-N 3-(5-hexylsulfinyl-1,3,4-thiadiazol-2-yl)-1,1-dimethylurea Chemical compound CCCCCCS(=O)C1=NN=C(S1)NC(=O)N(C)C UELVORNTLCQNFH-UHFFFAOYSA-N 0.000 claims 3
- CISJTFJIGIXLHO-UHFFFAOYSA-N 3-(5-hexylsulfonyl-1,3,4-thiadiazol-2-yl)-1,1-dimethylurea Chemical compound CN(C(=O)N=C1SC(=NN1)S(=O)(=O)CCCCCC)C CISJTFJIGIXLHO-UHFFFAOYSA-N 0.000 claims 3
- OQDBQQKROMZPGT-UHFFFAOYSA-N 1,1-dimethyl-3-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CN(C)C(=O)NC1=NN=C(S1)S(=O)C OQDBQQKROMZPGT-UHFFFAOYSA-N 0.000 claims 2
- PRQMEMARDGHXHK-UHFFFAOYSA-N 1,1-dimethyl-3-(5-prop-2-ynylsulfanyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CN(C)C(=O)NC1=NN=C(S1)SCC#C PRQMEMARDGHXHK-UHFFFAOYSA-N 0.000 claims 2
- VGLIMTJJGCXMNZ-UHFFFAOYSA-N 1,1-dimethyl-3-(5-propylsulfinyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CCCS(=O)C1=NN=C(S1)NC(=O)N(C)C VGLIMTJJGCXMNZ-UHFFFAOYSA-N 0.000 claims 2
- VODPBWXMJPZDJF-UHFFFAOYSA-N 1,1-dimethyl-3-[5-(2-methylprop-2-enylsulfanyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CC(=C)CSC1=NN=C(S1)NC(=O)N(C)C VODPBWXMJPZDJF-UHFFFAOYSA-N 0.000 claims 2
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 claims 1
- HHQJJOQNRLPQJF-UHFFFAOYSA-N 3-(5-ethylsulfonyl-1,3,4-thiadiazol-2-yl)-1,1-dimethylurea Chemical compound CCS(=O)(=O)C1=NN=C(NC(=O)N(C)C)S1 HHQJJOQNRLPQJF-UHFFFAOYSA-N 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 239000013543 active substance Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 241000219198 Brassica Species 0.000 description 5
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- 229910052700 potassium Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- LPXPCDVHAXMSRH-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-5-ethylsulfanyl-n,n-dimethyl-1,3,4-thiadiazole-3-carboxamide Chemical compound CCSC1=NN(C(=O)N(C)C)C(=NC(=O)N(C)C)S1 LPXPCDVHAXMSRH-UHFFFAOYSA-N 0.000 description 1
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([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
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- MIKLBXXZYUBIIG-UHFFFAOYSA-N lithium 2-propan-2-ylsulfanyl-1-thia-4-aza-3-azanidacyclopent-4-ene Chemical compound [Li+].C(C)(C)SC1SC=N[N-]1 MIKLBXXZYUBIIG-UHFFFAOYSA-N 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- 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
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material 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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762607481 DE2607481A1 (de) | 1976-02-20 | 1976-02-20 | 2-dimethylcarbamoylimino-1,3,4- thiadiazolin-3-id-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1577523A true GB1577523A (en) | 1980-10-22 |
Family
ID=5970729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7192/77A Expired GB1577523A (en) | 1976-02-20 | 1977-02-21 | Herbicidally active 2-dimethylcarbamoylimino-1,3,4-thiadiazolin-3-ide derivatives process for their manufacture and their use |
Country Status (32)
| Country | Link |
|---|---|
| JP (1) | JPS52102277A (OSRAM) |
| AR (1) | AR217638A1 (OSRAM) |
| AT (1) | AT351314B (OSRAM) |
| AU (1) | AU2186377A (OSRAM) |
| BE (1) | BE851600A (OSRAM) |
| BG (1) | BG27713A3 (OSRAM) |
| BR (1) | BR7700890A (OSRAM) |
| CA (1) | CA1077044A (OSRAM) |
| CS (1) | CS193083B2 (OSRAM) |
| DD (1) | DD128655A5 (OSRAM) |
| DE (1) | DE2607481A1 (OSRAM) |
| DK (1) | DK29577A (OSRAM) |
| EG (1) | EG12458A (OSRAM) |
| ES (1) | ES456051A1 (OSRAM) |
| FI (1) | FI770452A7 (OSRAM) |
| FR (1) | FR2341573A1 (OSRAM) |
| GB (1) | GB1577523A (OSRAM) |
| GR (1) | GR62395B (OSRAM) |
| IE (1) | IE44565B1 (OSRAM) |
| IL (1) | IL51461A (OSRAM) |
| IN (1) | IN155287B (OSRAM) |
| IT (1) | IT1118003B (OSRAM) |
| LU (1) | LU76741A1 (OSRAM) |
| NL (1) | NL7701752A (OSRAM) |
| NZ (1) | NZ183378A (OSRAM) |
| PL (1) | PL101774B1 (OSRAM) |
| PT (1) | PT66210B (OSRAM) |
| RO (1) | RO73052A (OSRAM) |
| SE (1) | SE7701776L (OSRAM) |
| SU (2) | SU648098A3 (OSRAM) |
| TR (1) | TR20545A (OSRAM) |
| ZA (1) | ZA77985B (OSRAM) |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3565901A (en) * | 1969-01-29 | 1971-02-23 | Air Prod & Chem | Certain salts of 1,3,4-thiadiazol-2-ylureas |
| GB1290223A (OSRAM) * | 1969-04-21 | 1972-09-20 | ||
| CH554886A (fr) * | 1970-01-15 | 1974-10-15 | Air Prod & Chem | Procede de preparation de thiadiazoles. |
| CH570391A5 (en) * | 1970-01-15 | 1975-12-15 | Air Prod & Chem | 1,3,4-Thiadiazole herbicides and fungicides - prepd. by reaction of carbamoyl chlorides with alkali metal derivs. of 2-amino-1,3,4-thiadiazoles |
| CH556862A (en) * | 1970-01-15 | 1974-12-13 | Air Prod & Chem | 1-(1,3,4-Thiadiazol-2-yl)-urea derivs as herbicides - and fungicides, prepd. from 2-amino-1,3,4-thiadiazoles |
| DE2028778A1 (en) * | 1970-06-06 | 1971-12-23 | Thiadiazolyl-urea herbicides - 5 - substd by sulphinyl or sulphonyl | |
| DE2044442C2 (de) * | 1970-09-03 | 1983-11-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3-(-5-Äthylsulfonyl-1,3,4-Thiadiazol-2-yl)-Harnstoff mit herbizider Wirkung |
| JPS5235672B2 (OSRAM) * | 1972-05-22 | 1977-09-10 | ||
| DE2246461C2 (de) * | 1972-09-21 | 1985-07-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3-(5-Butylsulfonyl-1,3,4-thiadiazol-2-yl)-harnstoff und herbizide Mittel enthaltend diese Verbindung |
| FR2237894A1 (en) * | 1973-06-29 | 1975-02-14 | Velsicol Chemical Corp | Thidiazolyl ureidoacetaldehyde acetals - as herbicies |
| DE2341816A1 (de) * | 1973-08-16 | 1975-02-27 | Schering Ag | Herbizide 1,3,4-thiadiazol-2-ylharnstoffe |
| DE2350709A1 (de) * | 1973-10-05 | 1975-04-24 | Schering Ag | 1,3,4-thiadiazol-2-yl-harnstoffe mit selektiv-herbizider wirkung |
| JPS583585B2 (ja) * | 1977-06-10 | 1983-01-21 | 株式会社日立製作所 | 電子顕徴鏡等の試料室 |
-
1976
- 1976-02-20 DE DE19762607481 patent/DE2607481A1/de not_active Withdrawn
-
1977
- 1977-01-07 RO RO7788970A patent/RO73052A/ro unknown
- 1977-01-13 SU SU772439828A patent/SU648098A3/ru active
- 1977-01-25 DK DK29577A patent/DK29577A/da unknown
- 1977-01-29 IN IN127/CAL/77A patent/IN155287B/en unknown
- 1977-02-01 CS CS77664A patent/CS193083B2/cs unknown
- 1977-02-02 AR AR266423A patent/AR217638A1/es active
- 1977-02-02 AU AU21863/77A patent/AU2186377A/en not_active Expired
- 1977-02-03 BG BG035323A patent/BG27713A3/xx unknown
- 1977-02-10 CA CA271,481A patent/CA1077044A/en not_active Expired
- 1977-02-10 LU LU76741A patent/LU76741A1/xx unknown
- 1977-02-11 FI FI770452A patent/FI770452A7/fi not_active Application Discontinuation
- 1977-02-11 TR TR20545A patent/TR20545A/xx unknown
- 1977-02-14 BR BR7700890A patent/BR7700890A/pt unknown
- 1977-02-16 IL IL51461A patent/IL51461A/xx unknown
- 1977-02-17 SE SE7701776A patent/SE7701776L/xx unknown
- 1977-02-18 PL PL1977196093A patent/PL101774B1/pl unknown
- 1977-02-18 IE IE346/77A patent/IE44565B1/en unknown
- 1977-02-18 SU SU772453508A patent/SU605520A3/ru active
- 1977-02-18 DD DD7700197438A patent/DD128655A5/xx unknown
- 1977-02-18 PT PT66210A patent/PT66210B/pt unknown
- 1977-02-18 GR GR52805A patent/GR62395B/el unknown
- 1977-02-18 IT IT20428/77A patent/IT1118003B/it active
- 1977-02-18 ZA ZA770985A patent/ZA77985B/xx unknown
- 1977-02-18 ES ES456051A patent/ES456051A1/es not_active Expired
- 1977-02-18 NZ NZ183378A patent/NZ183378A/xx unknown
- 1977-02-18 BE BE175074A patent/BE851600A/xx unknown
- 1977-02-18 AT AT111377A patent/AT351314B/de not_active IP Right Cessation
- 1977-02-18 NL NL7701752A patent/NL7701752A/xx not_active Application Discontinuation
- 1977-02-19 EG EG97/77A patent/EG12458A/xx active
- 1977-02-21 JP JP1802077A patent/JPS52102277A/ja active Pending
- 1977-02-21 FR FR7704886A patent/FR2341573A1/fr not_active Withdrawn
- 1977-02-21 GB GB7192/77A patent/GB1577523A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU648098A3 (ru) | 1979-02-15 |
| AU2186377A (en) | 1978-08-10 |
| EG12458A (en) | 1979-03-31 |
| BE851600A (fr) | 1977-08-18 |
| IE44565L (en) | 1977-08-20 |
| GR62395B (en) | 1979-04-10 |
| IL51461A0 (en) | 1977-04-29 |
| CA1077044A (en) | 1980-05-06 |
| PT66210A (de) | 1977-03-01 |
| BG27713A3 (bg) | 1979-12-12 |
| RO73052A (ro) | 1982-05-10 |
| IL51461A (en) | 1980-03-31 |
| SE7701776L (sv) | 1977-08-21 |
| FR2341573A1 (fr) | 1977-09-16 |
| DK29577A (da) | 1977-08-21 |
| TR20545A (tr) | 1981-10-15 |
| ZA77985B (en) | 1977-12-28 |
| DE2607481A1 (de) | 1977-08-25 |
| CS193083B2 (en) | 1979-09-17 |
| LU76741A1 (OSRAM) | 1977-06-30 |
| IT1118003B (it) | 1986-02-24 |
| DD128655A5 (de) | 1977-11-30 |
| SU605520A3 (ru) | 1978-04-30 |
| PL101774B1 (pl) | 1979-01-31 |
| AT351314B (de) | 1979-07-25 |
| FI770452A7 (OSRAM) | 1977-08-21 |
| JPS52102277A (en) | 1977-08-27 |
| NZ183378A (en) | 1979-01-11 |
| IN155287B (OSRAM) | 1985-01-12 |
| NL7701752A (nl) | 1977-08-23 |
| PT66210B (de) | 1978-07-12 |
| BR7700890A (pt) | 1977-10-18 |
| AR217638A1 (es) | 1980-04-15 |
| IE44565B1 (en) | 1982-01-13 |
| ATA111377A (de) | 1978-12-15 |
| ES456051A1 (es) | 1978-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |