DE2042110C3 - Substituierte Phenylthionocarbamate, Verfahren zu ihrer Herstellung und solche Carbamate enthaltende herbizide Mittel - Google Patents
Substituierte Phenylthionocarbamate, Verfahren zu ihrer Herstellung und solche Carbamate enthaltende herbizide MittelInfo
- Publication number
- DE2042110C3 DE2042110C3 DE2042110A DE2042110A DE2042110C3 DE 2042110 C3 DE2042110 C3 DE 2042110C3 DE 2042110 A DE2042110 A DE 2042110A DE 2042110 A DE2042110 A DE 2042110A DE 2042110 C3 DE2042110 C3 DE 2042110C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- thionocarbamate
- phenyl
- carbamoyloxy
- acid
- 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
- 230000002363 herbicidal effect Effects 0.000 title description 11
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 5
- 239000000203 mixture Substances 0.000 title description 4
- BMBJSXKEXRFGAV-UHFFFAOYSA-N phenylcarbamothioic s-acid Chemical class SC(=O)NC1=CC=CC=C1 BMBJSXKEXRFGAV-UHFFFAOYSA-N 0.000 title description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- -1 halogenoethyl Chemical group 0.000 description 33
- 239000004480 active ingredient Substances 0.000 description 21
- 244000178937 Brassica oleracea var. capitata Species 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 14
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 5
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 3
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- UBMONMNZSGNXMV-UHFFFAOYSA-N (3-aminophenyl) carbamate Chemical compound NC(=O)OC1=CC=CC(N)=C1 UBMONMNZSGNXMV-UHFFFAOYSA-N 0.000 description 2
- 229940018563 3-aminophenol Drugs 0.000 description 2
- 235000004221 Brassica oleracea var gemmifera Nutrition 0.000 description 2
- 244000308368 Brassica oleracea var. gemmifera Species 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- TUAYUUVAVSRLIC-UHFFFAOYSA-N O-methyl N-(3-hydroxyphenyl)carbamothioate Chemical compound COC(NC1=CC(=CC=C1)O)=S TUAYUUVAVSRLIC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000008164 mustard oil Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 244000281940 Brassica oleracea var. costata Species 0.000 description 1
- KACGXUFNGOZMKC-UHFFFAOYSA-N COC(NC1=CC=CC=C1)=[S+]O Chemical compound COC(NC1=CC=CC=C1)=[S+]O KACGXUFNGOZMKC-UHFFFAOYSA-N 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 241001140714 Citrus latifolia Species 0.000 description 1
- 241001354404 Cyanus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000214240 Galinsoga parviflora Species 0.000 description 1
- 235000018914 Galinsoga parviflora Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000520028 Lamium Species 0.000 description 1
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 1
- 244000303225 Lamium amplexicaule Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FNLCLRVXMIXOQE-UHFFFAOYSA-N O-ethyl N-(3-hydroxyphenyl)carbamothioate Chemical compound CCOC(=S)Nc1cccc(O)c1 FNLCLRVXMIXOQE-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- DXNQLZJOTVNBOZ-UHFFFAOYSA-N [O]C(=O)Nc1ccccc1 Chemical group [O]C(=O)Nc1ccccc1 DXNQLZJOTVNBOZ-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 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
- 150000004891 diazines Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 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
- 235000009973 maize Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- GRSBAMVBFWRBBH-UHFFFAOYSA-N o-ethyl chloromethanethioate Chemical compound CCOC(Cl)=S GRSBAMVBFWRBBH-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- LHUNTIHZLBVJKW-UHFFFAOYSA-N phenyl n-sulfanylidenecarbamate Chemical class S=NC(=O)OC1=CC=CC=C1 LHUNTIHZLBVJKW-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 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
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/16—Salts of dithiocarbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Moulds For Moulding Plastics Or The Like (AREA)
- Heating, Cooling, Or Curing Plastics Or The Like In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (34)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2042110A DE2042110C3 (de) | 1970-08-20 | 1970-08-20 | Substituierte Phenylthionocarbamate, Verfahren zu ihrer Herstellung und solche Carbamate enthaltende herbizide Mittel |
| ZA714526A ZA714526B (en) | 1970-08-20 | 1971-07-08 | Substituted phenylthiocarbamates having a herbicidal activity and processes for their manufacture |
| YU01874/71A YU36159B (en) | 1970-08-20 | 1971-07-16 | Process for obtaining novel substituted phenlthiocarbamates with herbicidal activity |
| FI2030/71A FI56169C (fi) | 1970-08-20 | 1971-07-16 | Saosom herbicid foer kaolodlingar anvaendbar 0-metyl-n-(3-(n'-(3-metylfenyl)-karbamoyloxi)-fenyl)-tiokarbamat |
| ES393477A ES393477A1 (es) | 1970-08-20 | 1971-07-21 | Procedimiento para la preparacion de herbicidas. |
| CS5482A CS167938B2 (enExample) | 1970-08-20 | 1971-07-27 | |
| GB3512971A GB1362705A (en) | 1970-08-20 | 1971-07-27 | Substituted phenylthiocarbamates having a herbicidal activity and processes for their manufacture |
| CA119,327A CA975776A (en) | 1970-08-20 | 1971-07-28 | Substituted phenylthiocarbamates having a herbicidal activity and processes for their manufacture |
| DK370571AA DK130788B (da) | 1970-08-20 | 1971-07-28 | Phenylthiocarbamater til anvendelse i herbicider. |
| BR4980/71A BR7104980D0 (pt) | 1970-08-20 | 1971-08-04 | Processo para a preparacao de fenil tiocarbamatos substituidos e composicoes herbicidas a base destes |
| DD156961A DD102056A5 (enExample) | 1970-08-20 | 1971-08-05 | |
| IL37474A IL37474A (en) | 1970-08-20 | 1971-08-09 | M-carbamoyloxy-phenylthiocarbamates having a herbicidal activity and processes for their manufacture |
| IE1007/71A IE35500B1 (en) | 1970-08-20 | 1971-08-10 | Substituted phenylthiocarbamates having a herbicidal activity and processes for their manufacture |
| EG356/71A EG10378A (en) | 1970-08-20 | 1971-08-11 | Substituted phenylthio carbamates active as herbicides and process for their preparation |
| BG018326A BG18577A3 (bg) | 1970-08-20 | 1971-08-12 | Хербицидно средство |
| CH1220671A CH553173A (de) | 1970-08-20 | 1971-08-18 | Verfahren zur herstellung von substituierten phenylthiocarbamaten. |
| PH12763A PH10964A (en) | 1970-08-20 | 1971-08-18 | Substituted phenylthiocarbamates having a herbicidal activity |
| LU63744D LU63744A1 (enExample) | 1970-08-20 | 1971-08-18 | |
| AT722171A AT311714B (de) | 1970-08-20 | 1971-08-18 | Herbizide Mittel |
| PL1971150080A PL81787B1 (enExample) | 1970-08-20 | 1971-08-18 | |
| RO67995A RO61101A (enExample) | 1970-08-20 | 1971-08-19 | |
| AU32518/71A AU456914B2 (en) | 1970-08-20 | 1971-08-19 | Substituted phenylthccarbamates having a herbicidal activity and processes for their manufacture |
| SE10562/71A SE364706B (enExample) | 1970-08-20 | 1971-08-19 | |
| HUSC346A HU162897B (enExample) | 1970-08-20 | 1971-08-19 | |
| NO3085/71A NO134209C (enExample) | 1970-08-20 | 1971-08-19 | |
| RO76449A RO60883A (enExample) | 1970-08-20 | 1971-08-19 | |
| NO3058/71A NO134209B (enExample) | 1970-08-20 | 1971-08-19 | |
| SU1691718A SU404192A1 (ru) | 1971-08-19 | Гербицид | |
| OA54337A OA03781A (fr) | 1970-08-20 | 1971-08-20 | Phénylthiocarbamates substitués possédant une activité herbicide et leur préparation. |
| NL7111549A NL7111549A (enExample) | 1970-08-20 | 1971-08-20 | |
| JP46063538A JPS5015848B1 (enExample) | 1970-08-20 | 1971-08-20 | |
| BE771600A BE771600A (fr) | 1970-08-20 | 1971-08-20 | Thiocarbamates de phenyle substitues et leur procede de preparation |
| FR7130373A FR2104583A5 (enExample) | 1970-08-20 | 1971-08-20 | |
| US05/672,940 US4076518A (en) | 1970-08-20 | 1976-04-02 | Substituted phenyl thiocarbamates with herbicidal action and method for their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2042110A DE2042110C3 (de) | 1970-08-20 | 1970-08-20 | Substituierte Phenylthionocarbamate, Verfahren zu ihrer Herstellung und solche Carbamate enthaltende herbizide Mittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2042110A1 DE2042110A1 (de) | 1972-02-24 |
| DE2042110B2 DE2042110B2 (de) | 1978-10-26 |
| DE2042110C3 true DE2042110C3 (de) | 1979-06-21 |
Family
ID=5780676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2042110A Expired DE2042110C3 (de) | 1970-08-20 | 1970-08-20 | Substituierte Phenylthionocarbamate, Verfahren zu ihrer Herstellung und solche Carbamate enthaltende herbizide Mittel |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS5015848B1 (enExample) |
| AT (1) | AT311714B (enExample) |
| AU (1) | AU456914B2 (enExample) |
| BE (1) | BE771600A (enExample) |
| BG (1) | BG18577A3 (enExample) |
| BR (1) | BR7104980D0 (enExample) |
| CA (1) | CA975776A (enExample) |
| CH (1) | CH553173A (enExample) |
| CS (1) | CS167938B2 (enExample) |
| DD (1) | DD102056A5 (enExample) |
| DE (1) | DE2042110C3 (enExample) |
| DK (1) | DK130788B (enExample) |
| EG (1) | EG10378A (enExample) |
| ES (1) | ES393477A1 (enExample) |
| FI (1) | FI56169C (enExample) |
| FR (1) | FR2104583A5 (enExample) |
| GB (1) | GB1362705A (enExample) |
| HU (1) | HU162897B (enExample) |
| IE (1) | IE35500B1 (enExample) |
| IL (1) | IL37474A (enExample) |
| LU (1) | LU63744A1 (enExample) |
| NL (1) | NL7111549A (enExample) |
| NO (2) | NO134209C (enExample) |
| OA (1) | OA03781A (enExample) |
| PH (1) | PH10964A (enExample) |
| PL (1) | PL81787B1 (enExample) |
| RO (2) | RO60883A (enExample) |
| SE (1) | SE364706B (enExample) |
| YU (1) | YU36159B (enExample) |
| ZA (1) | ZA714526B (enExample) |
-
1970
- 1970-08-20 DE DE2042110A patent/DE2042110C3/de not_active Expired
-
1971
- 1971-07-08 ZA ZA714526A patent/ZA714526B/xx unknown
- 1971-07-16 YU YU01874/71A patent/YU36159B/xx unknown
- 1971-07-16 FI FI2030/71A patent/FI56169C/fi active
- 1971-07-21 ES ES393477A patent/ES393477A1/es not_active Expired
- 1971-07-27 CS CS5482A patent/CS167938B2/cs unknown
- 1971-07-27 GB GB3512971A patent/GB1362705A/en not_active Expired
- 1971-07-28 CA CA119,327A patent/CA975776A/en not_active Expired
- 1971-07-28 DK DK370571AA patent/DK130788B/da unknown
- 1971-08-04 BR BR4980/71A patent/BR7104980D0/pt unknown
- 1971-08-05 DD DD156961A patent/DD102056A5/xx unknown
- 1971-08-09 IL IL37474A patent/IL37474A/xx unknown
- 1971-08-10 IE IE1007/71A patent/IE35500B1/xx unknown
- 1971-08-11 EG EG356/71A patent/EG10378A/xx active
- 1971-08-12 BG BG018326A patent/BG18577A3/xx unknown
- 1971-08-18 PH PH12763A patent/PH10964A/en unknown
- 1971-08-18 CH CH1220671A patent/CH553173A/xx not_active IP Right Cessation
- 1971-08-18 LU LU63744D patent/LU63744A1/xx unknown
- 1971-08-18 PL PL1971150080A patent/PL81787B1/pl unknown
- 1971-08-18 AT AT722171A patent/AT311714B/de not_active IP Right Cessation
- 1971-08-19 HU HUSC346A patent/HU162897B/hu unknown
- 1971-08-19 RO RO76449A patent/RO60883A/ro unknown
- 1971-08-19 SE SE10562/71A patent/SE364706B/xx unknown
- 1971-08-19 NO NO3085/71A patent/NO134209C/no unknown
- 1971-08-19 AU AU32518/71A patent/AU456914B2/en not_active Expired
- 1971-08-19 RO RO67995A patent/RO61101A/ro unknown
- 1971-08-19 NO NO3058/71A patent/NO134209B/no unknown
- 1971-08-20 OA OA54337A patent/OA03781A/xx unknown
- 1971-08-20 FR FR7130373A patent/FR2104583A5/fr not_active Expired
- 1971-08-20 NL NL7111549A patent/NL7111549A/xx not_active Application Discontinuation
- 1971-08-20 JP JP46063538A patent/JPS5015848B1/ja active Pending
- 1971-08-20 BE BE771600A patent/BE771600A/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1567151C3 (de) | Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende herbizide Mittel | |
| DE3618662A1 (de) | Trisubstituierte 1,3,5-triazin-2,4,6-trione | |
| DE1567164C2 (de) | Herbizide Mittel auf Basis von N-Carbamoyloxyphenyl-Carbamaten | |
| DE2101938C2 (de) | 3-[2-Chlor-4-(3,3-dimethylureido)-phenyl]-5-tert.-butyl-1,3,4-oxadiazolon-(2), seine Herstellung und herbicide Zusammensetzungen, die es enthalten | |
| EP0037971B1 (de) | Trisubstituierte Cyanguanidine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| DE2945530A1 (de) | Harnstoffe mit cyclischen substituenten, ihre herstellung und verwendung als herbizide | |
| DE2108975C3 (de) | N-Acyl-Diurethane sowie diese enthaltendes herbizides Mittel | |
| DE2928410A1 (de) | Acylharnstoffe, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung | |
| DE1593520C3 (de) | 3-(Carbamoyloxyphenyl)-harnstoffe bzw. -thioharnstoffe, diese enthaltende Mittel mit selektiver herbizider Wirkung sowie Verfahren zu deren Herstellung | |
| EP0257294B1 (de) | E/Z-Isomerengemische und reine Z-Isomere von N alpha-(2-Cyan-2-alkoximinoacetyl) aminosäurederivaten und- peptiden | |
| DE1567044A1 (de) | Pestizides,insbesondere herbizides Mittel | |
| DE2121957C3 (de) | Diurethane sowie diese enthaltende herbizide Mittel | |
| DE2210540C2 (de) | Cyanphenylcarbonate, Verfahren zu deren Herstellung sowie diese enthaltende herbizide Mittel | |
| DE2042110B2 (de) | Substituierte Phenylthionocarbamate, Verfahren zu ihrer Herstellung und solche Carbamate enthaltende herbizide Mittel | |
| DE2310648C3 (de) | Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende selektive herbizide Mittel | |
| DE2310649C3 (de) | Diurethane sowie diese enthaltende selektive herbizide Mittel | |
| DE1567022A1 (de) | Herbizid | |
| DE2320362A1 (de) | Dichlorthiazolylharnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide | |
| DE2843691A1 (de) | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel | |
| DE1932827B2 (de) | Cycloaliphatische imidazolidin-2-on- 1-carbonsaeure-amide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide | |
| DE2003143C3 (de) | N-Arylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende herbicide Mittel | |
| AT275961B (de) | Herbizide Mittel mit verstärkter Wirksamkeit | |
| DE3214227A1 (de) | 1-(trihalogenmethyl-sulfenyl)-4-methylimidazol-5-carboxamide und diese enthaltende fungizide | |
| DE1668003C3 (de) | 3-Chlor-4-trifluormethylphenylhamstoffe, Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von Unkräutern | |
| DE1567163C3 (de) | Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie herbizide und algizide Mittel enthaltend diese Verbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |