GB1583271A - Herbicidally active 2-(dimethylcarbamoylimino)-1,3,4-thiadiazolin-3-carboxylic acid esters process for their manufacture and their use - Google Patents
Herbicidally active 2-(dimethylcarbamoylimino)-1,3,4-thiadiazolin-3-carboxylic acid esters process for their manufacture and their use Download PDFInfo
- Publication number
- GB1583271A GB1583271A GB18232/77A GB1823277A GB1583271A GB 1583271 A GB1583271 A GB 1583271A GB 18232/77 A GB18232/77 A GB 18232/77A GB 1823277 A GB1823277 A GB 1823277A GB 1583271 A GB1583271 A GB 1583271A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethylcarbamoylimino
- carboxylic acid
- thiadiazolin
- ester
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- PNWXIVHAFKHCRF-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylic acid Chemical class CN(C(=O)N=C1SC=NN1C(=O)O)C PNWXIVHAFKHCRF-UHFFFAOYSA-N 0.000 title claims description 3
- -1 Ethylthio 2 (dimethylcarbamoylimino) 1,3,4 thiadiazolin Chemical compound 0.000 claims description 134
- 150000001875 compounds Chemical class 0.000 claims description 92
- 241000196324 Embryophyta Species 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 230000002363 herbicidal effect Effects 0.000 claims description 15
- 150000002736 metal compounds Chemical class 0.000 claims description 13
- 239000004009 herbicide Substances 0.000 claims description 9
- 239000007800 oxidant agent Substances 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- UIOKUCVRQRCTOG-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-ethylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)SCC)=NC(N(C)C)=O UIOKUCVRQRCTOG-UHFFFAOYSA-N 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 239000002699 waste material Substances 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 3
- TWWMBNSWODEWEW-UHFFFAOYSA-N 2H-1,3,4-thiadiazole-3-carboxylic acid Chemical compound S1C=NN(C1)C(=O)O TWWMBNSWODEWEW-UHFFFAOYSA-N 0.000 claims description 3
- OVFGZYLIJLMMOS-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-ethylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)OC(=O)N1C(SC(=N1)SCC)=NC(N(C)C)=O OVFGZYLIJLMMOS-UHFFFAOYSA-N 0.000 claims description 3
- CPFFMIWOJNRVDE-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1N=C(SC)SC1=NC(=O)N(C)C CPFFMIWOJNRVDE-UHFFFAOYSA-N 0.000 claims description 3
- WFKJKLPLEWIXLO-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-5-propylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCS(=O)(=O)C1=NN(C(=O)OC(C)C)C(=NC(=O)N(C)C)S1 WFKJKLPLEWIXLO-UHFFFAOYSA-N 0.000 claims description 3
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical class CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 claims description 2
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 claims description 2
- AYLWYVAKWIUMPJ-UHFFFAOYSA-N 2-methylpropyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CC(C)COC(=O)N1N=C(S(C)(=O)=O)SC1=NC(=O)N(C)C AYLWYVAKWIUMPJ-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
- 240000005979 Hordeum vulgare Species 0.000 claims description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 240000004713 Pisum sativum Species 0.000 claims description 2
- 235000010582 Pisum sativum Nutrition 0.000 claims description 2
- 244000061456 Solanum tuberosum Species 0.000 claims description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
- 235000021307 Triticum Nutrition 0.000 claims description 2
- 244000098338 Triticum aestivum Species 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
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- SYHNGBXGISEMEC-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-(2-methylprop-2-enylsulfanyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SCC(=C)C)=NC(N(C)C)=O SYHNGBXGISEMEC-UHFFFAOYSA-N 0.000 claims description 2
- VXHCZOQTDNVASO-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-(2-methylpropylsulfonyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)CC(C)C)=NC(N(C)C)=O VXHCZOQTDNVASO-UHFFFAOYSA-N 0.000 claims description 2
- DOUXLYWKNBLYRU-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-hexylsulfinyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)CCCCCC)=NC(N(C)C)=O DOUXLYWKNBLYRU-UHFFFAOYSA-N 0.000 claims description 2
- RUUBHXQXIINWNE-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-pentylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SCCCCC)=NC(N(C)C)=O RUUBHXQXIINWNE-UHFFFAOYSA-N 0.000 claims description 2
- MMZCPCKRLGYQJR-UHFFFAOYSA-N butyl 5-butylsulfonyl-2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)CCCC)=NC(N(C)C)=O MMZCPCKRLGYQJR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- PQHUNICQRBELNW-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCOC(=O)N1N=C(SC)SC1=NC(=O)N(C)C PQHUNICQRBELNW-UHFFFAOYSA-N 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 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
- 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
- JWFKMJXJIRILME-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-(2-methylprop-2-enylsulfanyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1N=C(SCC(C)=C)SC1=NC(=O)N(C)C JWFKMJXJIRILME-UHFFFAOYSA-N 0.000 claims description 2
- SPEDCIDJBOQOLU-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-propylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCSC1=NN(C(=O)OC)C(=NC(=O)N(C)C)S1 SPEDCIDJBOQOLU-UHFFFAOYSA-N 0.000 claims description 2
- NTVVQODQIKFJKZ-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-propylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)SCCC)=NC(N(C)C)=O NTVVQODQIKFJKZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- ABZMLLKVVODUGL-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CN(C)C(=O)N=C1SC(S(C)(=O)=O)=NN1C(=O)OCC=C ABZMLLKVVODUGL-UHFFFAOYSA-N 0.000 claims description 2
- SMRXPJJNPPOUAO-UHFFFAOYSA-N prop-2-ynyl 2-(dimethylcarbamoylimino)-5-(2-methylpropylsulfonyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C#C)OC(=O)N1C(SC(=N1)S(=O)(=O)CC(C)C)=NC(N(C)C)=O SMRXPJJNPPOUAO-UHFFFAOYSA-N 0.000 claims description 2
- HVPAJZYCKDTFSO-UHFFFAOYSA-N prop-2-ynyl 2-(dimethylcarbamoylimino)-5-pentylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C#C)OC(=O)N1C(SC(=N1)S(=O)(=O)CCCCC)=NC(N(C)C)=O HVPAJZYCKDTFSO-UHFFFAOYSA-N 0.000 claims description 2
- AFLGLGACODWYCU-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-5-ethylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCSC1=NN(C(=O)OC(C)C)C(=NC(=O)N(C)C)S1 AFLGLGACODWYCU-UHFFFAOYSA-N 0.000 claims description 2
- BFZUTKGQUKGURD-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-5-propylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCSC1=NN(C(=O)OC(C)C)C(=NC(=O)N(C)C)S1 BFZUTKGQUKGURD-UHFFFAOYSA-N 0.000 claims description 2
- WHDCAAUJQJHRLP-UHFFFAOYSA-N propyl 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CC)OC(=O)N1C(SC(=N1)SCCCCCC)=NC(N(C)C)=O WHDCAAUJQJHRLP-UHFFFAOYSA-N 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- NITRGUSNTHABMT-UHFFFAOYSA-N 2,2,2-trichloroethyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CSC1=NN(C(=O)OCC(Cl)(Cl)Cl)C(=NC(=O)N(C)C)S1 NITRGUSNTHABMT-UHFFFAOYSA-N 0.000 claims 1
- QDWYHFRTJNLKGU-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylic acid Chemical compound CN(C(=O)N=C1SC(=NN1C(=O)O)SC)C QDWYHFRTJNLKGU-UHFFFAOYSA-N 0.000 claims 1
- PMRUKVCRVFJRCV-UHFFFAOYSA-N 2-methylpropyl 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C(C)C)OC(=O)N1C(SC(=N1)SCCCCCC)=NC(N(C)C)=O PMRUKVCRVFJRCV-UHFFFAOYSA-N 0.000 claims 1
- WJWPGCWZJCWDCO-UHFFFAOYSA-N 2-methylpropyl 2-(dimethylcarbamoylimino)-5-hexylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCCCCS(=O)(=O)C1=NN(C(=O)OCC(C)C)C(=NC(=O)N(C)C)S1 WJWPGCWZJCWDCO-UHFFFAOYSA-N 0.000 claims 1
- PHGPCARYJWOZOV-UHFFFAOYSA-N 2-methylpropyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CSC1=NN(C(=O)OCC(C)C)C(=NC(=O)N(C)C)S1 PHGPCARYJWOZOV-UHFFFAOYSA-N 0.000 claims 1
- LNGORYLUJOKKDE-UHFFFAOYSA-N 3-chloropropyl 2-(dimethylcarbamoylimino)-5-propylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCSC1=NN(C(=O)OCCCCl)C(=NC(=O)N(C)C)S1 LNGORYLUJOKKDE-UHFFFAOYSA-N 0.000 claims 1
- 240000006394 Sorghum bicolor Species 0.000 claims 1
- MNWBHFFKAXSNBL-UHFFFAOYSA-N benzyl 2-(dimethylcarbamoylimino)-5-ethylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC(=O)N1C(SC(=N1)SCC)=NC(N(C)C)=O MNWBHFFKAXSNBL-UHFFFAOYSA-N 0.000 claims 1
- ADEXXHUUUUVMRL-UHFFFAOYSA-N benzyl 2-(dimethylcarbamoylimino)-5-ethylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC(=O)N1C(SC(=N1)S(=O)(=O)CC)=NC(N(C)C)=O ADEXXHUUUUVMRL-UHFFFAOYSA-N 0.000 claims 1
- AFWVBPDRQSUBHX-UHFFFAOYSA-N benzyl 2-(dimethylcarbamoylimino)-5-pentylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC(=O)N1C(SC(=N1)SCCCCC)=NC(N(C)C)=O AFWVBPDRQSUBHX-UHFFFAOYSA-N 0.000 claims 1
- ATVSVKZZVQKCJU-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SCCCCCC)=NC(N(C)C)=O ATVSVKZZVQKCJU-UHFFFAOYSA-N 0.000 claims 1
- YFXPCVAXBXYKPG-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-hexylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)CCCCCC)=NC(N(C)C)=O YFXPCVAXBXYKPG-UHFFFAOYSA-N 0.000 claims 1
- ZSVHBDFRUWPVKA-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)C)=NC(N(C)C)=O ZSVHBDFRUWPVKA-UHFFFAOYSA-N 0.000 claims 1
- WOUZLXVBMOTPNP-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-prop-2-enylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SCC=C)=NC(N(C)C)=O WOUZLXVBMOTPNP-UHFFFAOYSA-N 0.000 claims 1
- HYCPJJSOQOUYMK-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SC(C)C)=NC(N(C)C)=O HYCPJJSOQOUYMK-UHFFFAOYSA-N 0.000 claims 1
- ZKQACGNMTPDKJK-UHFFFAOYSA-N butyl 5-butylsulfanyl-2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SCCCC)=NC(N(C)C)=O ZKQACGNMTPDKJK-UHFFFAOYSA-N 0.000 claims 1
- VWUWDLNNJGVACI-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-(2-methylprop-2-enylsulfanyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)OC(=O)N1C(SC(=N1)SCC(=C)C)=NC(N(C)C)=O VWUWDLNNJGVACI-UHFFFAOYSA-N 0.000 claims 1
- MESJFFQDKMUSPD-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-(2-methylprop-2-enylsulfonyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)OC(=O)N1C(SC(=N1)S(=O)(=O)CC(=C)C)=NC(N(C)C)=O MESJFFQDKMUSPD-UHFFFAOYSA-N 0.000 claims 1
- GFVQHFDOPMKUFO-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-ethylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCOC(=O)N1N=C(S(=O)(=O)CC)SC1=NC(=O)N(C)C GFVQHFDOPMKUFO-UHFFFAOYSA-N 0.000 claims 1
- RGKYKNZRPPLJCY-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)OC(=O)N1C(SC(=N1)SCCCCCC)=NC(N(C)C)=O RGKYKNZRPPLJCY-UHFFFAOYSA-N 0.000 claims 1
- UMRWCJFXLYJWES-UHFFFAOYSA-N hexyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCCC)OC(=O)N1C(SC(=N1)SC)=NC(N(C)C)=O UMRWCJFXLYJWES-UHFFFAOYSA-N 0.000 claims 1
- MKIZCXBFBRAUHT-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-ethylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCS(=O)(=O)C1=NN(C(=O)OC)C(=NC(=O)N(C)C)S1 MKIZCXBFBRAUHT-UHFFFAOYSA-N 0.000 claims 1
- YLCGVEMJQIIEGX-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCCCCSC1=NN(C(=O)OC)C(=NC(=O)N(C)C)S1 YLCGVEMJQIIEGX-UHFFFAOYSA-N 0.000 claims 1
- HOTXYOPRCDCSOP-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1N=C(S(C)(=O)=O)SC1=NC(=O)N(C)C HOTXYOPRCDCSOP-UHFFFAOYSA-N 0.000 claims 1
- LZJZKPWZKHFBTC-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-prop-2-enylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1N=C(SCC=C)SC1=NC(=O)N(C)C LZJZKPWZKHFBTC-UHFFFAOYSA-N 0.000 claims 1
- YCHYQWHDEFAUDW-UHFFFAOYSA-N methyl 5-but-2-enylsulfanyl-2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1N=C(SCC=CC)SC1=NC(=O)N(C)C YCHYQWHDEFAUDW-UHFFFAOYSA-N 0.000 claims 1
- RDEGPHUKFCYVRH-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)SC)=NC(N(C)C)=O RDEGPHUKFCYVRH-UHFFFAOYSA-N 0.000 claims 1
- GCHJRLPOSBCUSO-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)S(=O)(=O)C)=NC(N(C)C)=O GCHJRLPOSBCUSO-UHFFFAOYSA-N 0.000 claims 1
- WNRIXTZCYAFSJO-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)SC(C)C)=NC(N(C)C)=O WNRIXTZCYAFSJO-UHFFFAOYSA-N 0.000 claims 1
- PRQHFEVGGQJMSK-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)S(=O)(=O)C(C)C)=NC(N(C)C)=O PRQHFEVGGQJMSK-UHFFFAOYSA-N 0.000 claims 1
- LTQMKJDPXAGXDG-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-propylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)S(=O)(=O)CCC)=NC(N(C)C)=O LTQMKJDPXAGXDG-UHFFFAOYSA-N 0.000 claims 1
- QZMRVRCBMZXZME-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CSC1=NN(C(=O)OCC=C)C(=NC(=O)N(C)C)S1 QZMRVRCBMZXZME-UHFFFAOYSA-N 0.000 claims 1
- IAGBXQSMFXXOLQ-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CC(C)SC1=NN(C(=O)OCC=C)C(=NC(=O)N(C)C)S1 IAGBXQSMFXXOLQ-UHFFFAOYSA-N 0.000 claims 1
- FILXGDSYXYDAMN-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CC(C)S(=O)(=O)C1=NN(C(=O)OCC=C)C(=NC(=O)N(C)C)S1 FILXGDSYXYDAMN-UHFFFAOYSA-N 0.000 claims 1
- HACNBSYTQOAGBM-UHFFFAOYSA-N prop-2-enyl 5-but-2-enylsulfanyl-2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylate Chemical compound CC=CCSC1=NN(C(=O)OCC=C)C(=NC(=O)N(C)C)S1 HACNBSYTQOAGBM-UHFFFAOYSA-N 0.000 claims 1
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- 239000006028 limestone Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Inorganic materials O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 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
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- OEAMSRQVBHUCCJ-UHFFFAOYSA-N prop-2-enyl 2H-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C=C)OC(=O)N1CSC=N1 OEAMSRQVBHUCCJ-UHFFFAOYSA-N 0.000 description 1
- MSIHCVVMACRQMT-UHFFFAOYSA-N prop-2-ynyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C#C)OC(=O)N1C(SC(=N1)SC)=NC(N(C)C)=O MSIHCVVMACRQMT-UHFFFAOYSA-N 0.000 description 1
- MPGDMWCVIWYLSI-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)(C)OC(=O)N1C(SC(=N1)S(=O)(=O)C)=NC(N(C)C)=O MPGDMWCVIWYLSI-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 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
- 230000002194 synthesizing effect Effects 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 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
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762621647 DE2621647A1 (de) | 1976-05-13 | 1976-05-13 | 2-(dimethylcarbamoylimino)-1,3,4- thiadiazolin-3-carbonsaeure-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1583271A true GB1583271A (en) | 1981-01-21 |
Family
ID=5978046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18232/77A Expired GB1583271A (en) | 1976-05-13 | 1977-05-02 | Herbicidally active 2-(dimethylcarbamoylimino)-1,3,4-thiadiazolin-3-carboxylic acid esters process for their manufacture and their use |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4169718A (enExample) |
| JP (1) | JPS52139062A (enExample) |
| AT (1) | AT354802B (enExample) |
| AU (1) | AU2513377A (enExample) |
| BE (1) | BE854614A (enExample) |
| BG (1) | BG27716A3 (enExample) |
| CA (1) | CA1090808A (enExample) |
| CS (1) | CS192480B2 (enExample) |
| DD (1) | DD130201A5 (enExample) |
| DE (1) | DE2621647A1 (enExample) |
| DK (1) | DK114477A (enExample) |
| ES (1) | ES457730A1 (enExample) |
| FI (1) | FI771298A7 (enExample) |
| FR (1) | FR2351110A1 (enExample) |
| GB (1) | GB1583271A (enExample) |
| GR (1) | GR63745B (enExample) |
| IE (1) | IE45053B1 (enExample) |
| IL (1) | IL52033A (enExample) |
| IT (1) | IT1085078B (enExample) |
| LU (1) | LU76938A1 (enExample) |
| NL (1) | NL7703889A (enExample) |
| NO (1) | NO771675L (enExample) |
| PL (1) | PL102602B1 (enExample) |
| PT (1) | PT66533B (enExample) |
| RO (1) | RO72224A (enExample) |
| SE (1) | SE7705508L (enExample) |
| SU (2) | SU649320A3 (enExample) |
| TR (1) | TR19696A (enExample) |
| ZA (1) | ZA772869B (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL293262A (enExample) * | 1962-05-28 | |||
| DE2124260A1 (de) * | 1971-05-15 | 1972-11-30 | Farbenfabriken Bayer AG, 5090 Le verkusen | Verfahren zur Herstellung von 4 sub stituierten 1,3,4 Thiadiazolon (5) yl (2) harnstoffen |
-
1976
- 1976-05-13 DE DE19762621647 patent/DE2621647A1/de not_active Withdrawn
-
1977
- 1977-03-11 LU LU76938A patent/LU76938A1/xx unknown
- 1977-03-16 DK DK114477A patent/DK114477A/da unknown
- 1977-03-18 CS CS771820A patent/CS192480B2/cs unknown
- 1977-04-07 NL NL7703889A patent/NL7703889A/xx not_active Application Discontinuation
- 1977-04-12 SU SU772468202A patent/SU649320A3/ru active
- 1977-04-12 ES ES457730A patent/ES457730A1/es not_active Expired
- 1977-04-25 FI FI771298A patent/FI771298A7/fi not_active Application Discontinuation
- 1977-04-26 BG BG036125A patent/BG27716A3/xx unknown
- 1977-04-28 SU SU772475610A patent/SU648048A3/ru active
- 1977-05-02 GB GB18232/77A patent/GB1583271A/en not_active Expired
- 1977-05-05 IL IL52033A patent/IL52033A/xx unknown
- 1977-05-06 IE IE928/77A patent/IE45053B1/en unknown
- 1977-05-07 RO RO7790253A patent/RO72224A/ro unknown
- 1977-05-10 TR TR19696A patent/TR19696A/xx unknown
- 1977-05-10 US US05/795,642 patent/US4169718A/en not_active Expired - Lifetime
- 1977-05-11 DD DD7700198870A patent/DD130201A5/xx unknown
- 1977-05-11 SE SE7705508A patent/SE7705508L/xx unknown
- 1977-05-11 PL PL1977198027A patent/PL102602B1/pl unknown
- 1977-05-11 AT AT336177A patent/AT354802B/de not_active IP Right Cessation
- 1977-05-11 PT PT66533A patent/PT66533B/pt unknown
- 1977-05-11 GR GR53442A patent/GR63745B/el unknown
- 1977-05-12 IT IT23469/77A patent/IT1085078B/it active
- 1977-05-12 NO NO771675A patent/NO771675L/no unknown
- 1977-05-12 CA CA278,440A patent/CA1090808A/en not_active Expired
- 1977-05-13 ZA ZA00772869A patent/ZA772869B/xx unknown
- 1977-05-13 JP JP5523377A patent/JPS52139062A/ja active Granted
- 1977-05-13 FR FR7714692A patent/FR2351110A1/fr active Pending
- 1977-05-13 AU AU25133/77A patent/AU2513377A/en not_active Expired
- 1977-05-13 BE BE177559A patent/BE854614A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU76938A1 (enExample) | 1977-07-14 |
| JPS5538342B2 (enExample) | 1980-10-03 |
| NL7703889A (nl) | 1977-11-15 |
| ATA336177A (de) | 1979-06-15 |
| IL52033A (en) | 1980-03-31 |
| IL52033A0 (en) | 1977-07-31 |
| ES457730A1 (es) | 1978-02-16 |
| IE45053L (en) | 1977-11-13 |
| BG27716A3 (bg) | 1979-12-12 |
| DK114477A (da) | 1977-11-14 |
| NO771675L (no) | 1977-11-15 |
| SU649320A3 (ru) | 1979-02-25 |
| DE2621647A1 (de) | 1977-12-01 |
| US4169718A (en) | 1979-10-02 |
| ZA772869B (en) | 1978-03-29 |
| PL102602B1 (pl) | 1979-04-30 |
| JPS52139062A (en) | 1977-11-19 |
| FR2351110A1 (fr) | 1977-12-09 |
| SE7705508L (sv) | 1977-11-14 |
| AU2513377A (en) | 1978-11-16 |
| DD130201A5 (de) | 1978-03-15 |
| SU648048A3 (ru) | 1979-02-15 |
| CS192480B2 (en) | 1979-08-31 |
| PT66533B (de) | 1978-10-17 |
| IE45053B1 (en) | 1982-06-16 |
| PL198027A1 (pl) | 1978-02-13 |
| TR19696A (tr) | 1979-10-11 |
| FI771298A7 (enExample) | 1977-11-14 |
| RO72224A (ro) | 1982-05-10 |
| AT354802B (de) | 1979-01-25 |
| BE854614A (fr) | 1977-11-14 |
| PT66533A (de) | 1977-06-01 |
| GR63745B (en) | 1979-12-04 |
| CA1090808A (en) | 1980-12-02 |
| IT1085078B (it) | 1985-05-28 |
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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 |