JPS6151583B2 - - Google Patents
Info
- Publication number
- JPS6151583B2 JPS6151583B2 JP53065876A JP6587678A JPS6151583B2 JP S6151583 B2 JPS6151583 B2 JP S6151583B2 JP 53065876 A JP53065876 A JP 53065876A JP 6587678 A JP6587678 A JP 6587678A JP S6151583 B2 JPS6151583 B2 JP S6151583B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- weight
- parts
- alkyl
- halogen
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052736 halogen Chemical group 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- 241000196324 Embryophyta Species 0.000 description 26
- 239000013543 active substance Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- -1 chloroformate thioester Chemical class 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 230000002363 herbicidal effect Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 239000000047 product Substances 0.000 description 6
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 6
- 235000012239 silicon dioxide Nutrition 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 4
- 240000002791 Brassica napus Species 0.000 description 4
- 235000011293 Brassica napus Nutrition 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000010726 Vigna sinensis Nutrition 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- YSJKYAHYBFJVKV-UHFFFAOYSA-N ethyl n-nitrocarbamate Chemical compound CCOC(=O)N[N+]([O-])=O YSJKYAHYBFJVKV-UHFFFAOYSA-N 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- 235000021533 Beta vulgaris Nutrition 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 235000021538 Chard Nutrition 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241001506137 Rapa Species 0.000 description 3
- 241000219977 Vigna Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 229940018564 m-phenylenediamine Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- 244000291564 Allium cepa Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 2
- 235000007119 Ananas comosus Nutrition 0.000 description 2
- 235000005340 Asparagus officinalis Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 244000307700 Fragaria vesca Species 0.000 description 2
- 235000016623 Fragaria vesca Nutrition 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003230 Helianthus tuberosus Nutrition 0.000 description 2
- 240000008892 Helianthus tuberosus Species 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 240000004322 Lens culinaris Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000218657 Picea Species 0.000 description 2
- 240000005809 Prunus persica Species 0.000 description 2
- 235000014443 Pyrus communis Nutrition 0.000 description 2
- 240000001987 Pyrus communis Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 244000281247 Ribes rubrum Species 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- 244000000231 Sesamum indicum Species 0.000 description 2
- 235000003434 Sesamum indicum Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- 244000300264 Spinacia oleracea Species 0.000 description 2
- 235000009337 Spinacia oleracea Nutrition 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 244000299461 Theobroma cacao Species 0.000 description 2
- 235000009470 Theobroma cacao Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 235000010749 Vicia faba Nutrition 0.000 description 2
- 240000006677 Vicia faba Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000155 melt Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- VPGSXIKVUASQIY-UHFFFAOYSA-N 1,2-dibutylnaphthalene Chemical class C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 VPGSXIKVUASQIY-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- H—ELECTRICITY
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- H01L25/00—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof
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- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
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- A—HUMAN NECESSITIES
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- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
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- 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<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C271/38—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/62—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Power Engineering (AREA)
- Computer Hardware Design (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
本発明は優れた除草作用を有する新規の価値あ
る硫黄含有ジウレタン、これ等化合物を含有する
除草剤、及びこれ等化合物にて望ましからぬ植物
を撲滅する方法に係る。
メチル―Ｎ―（３―（N′―（3′―メチルフエニ
ルカルバモイルオキシ）―フエニル）―カルバマ
ート、エチル―Ｎ―（N′―フエニルカルバモイ
ルオキシ）―フエニル）―カルバマート、メチル
―Ｎ―（３―N′―メチル―N′―フエニルカルバ
モイルオキシ）―フエニル）―カルバマート（独
乙連邦共和国特許公告公報第1567151号）又は３
―イソプロピル―２，１，３―ベンゾチアジアジ
ノン―(4)―２，２―ジオキシド（独乙連邦共和国
特許公告公報第1542836号）を除草剤として使用
することは公知である。
然るに
一般式
（式中Ｚは残基
The present invention relates to novel and valuable sulfur-containing diurethanes with excellent herbicidal activity, herbicides containing these compounds, and methods for combating undesirable plants with these compounds. Methyl-N-(3-(N'-(3'-methylphenylcarbamoyloxy)-phenyl)-carbamate, Ethyl-N-(N'-phenylcarbamoyloxy)-phenyl)-carbamate, Methyl-N- (3-N'-methyl-N'-phenylcarbamoyloxy)-phenyl)-carbamate (Germany and Commonwealth Republic Patent Publication No. 1567151) or 3
It is known to use -isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide (German Patent Publication No. 1542836) as a herbicide. However, the general formula (In the formula, Z is a residue
【式】を意味し、Ｙ は残基[Formula] means Y is a residue
【式】を意味し、その際Ｚは常
にＹとは異なり、かつR1とR2は、それぞれ互い
に関係なく、水素，１〜４の炭素原子を有するア
ルキル、２〜４の炭素原子を有するアルコキシア
ルキル、３〜５の炭素原子を有するアルコキシカ
ルボニルアルキル、１〜４の炭素原子を有するハ
ロゲンアルキル、場合によつては１〜４の炭素原
子を有するアルキルまたはハロゲンで置換したベ
ンジルであり、R3およびR4は、それぞれ互いに
関係なく、１〜６の炭素原子を有する非置換アル
キルまたはハロゲンでまたは１〜２の炭素原子を
有するアルコキシでまたはハロゲンで置換または
非置換フエニルで置換した１〜４の炭素原子を有
するアルキシ、２〜４の炭素原子を有するアルケ
ニル、３〜４の炭素原子を有するアルキニル、場
合によつては１〜４の炭素原子を有するアルキル
で置換した５〜８の炭素原子を有するシクロアル
キル、７〜８の炭素原子を有するビシクロアルキ
ル、10〜15の炭素原子を有するトリシクロアルキ
ル、縮合環系を有するフエニル環、フエニル、一
重または多重に置換されたフエニル、置換基と共
に１〜４の炭素原子を有するアルキル、ハロゲ
ン、または１〜３の炭素原子を有するアルコキシ
であり、かつＸは、水素、１〜４の炭素原子を有
するアルキル、１〜３の炭素原子を有するハロゲ
ンアルキル、１〜２の炭素原子を有するアルコキ
シ、ハロゲン、ニトロ、またはアミノであり、ｎ
は１〜４であり、かつＡ，Ｂ，Ｄ，Ｅは、それぞ
れ互いに関係なく、酸素または硫黄であり、その
際すべての残基Ａ，Ｂ，Ｄ，Ｅが、同時に酸素で
あることはなく、かつその際これら残基の少なく
とも１つは常に硫黄を表わす）で示される新規の
硫黄含有ジウレタンが多数の主要な望ましからぬ
植物に対する良好な除草作用と同時に多くの栽培
植物に於ける良好な忍容性を有することが知られ
た。これ等作用は公知の有効物質の作用よりも良
好である。
新規の化合物は例えば次の方法に依り製造され
ることができ、この場合残基Ａ，Ｂ，Ｄ，E.R，
R1，R2，R3.R4，Ｘ及びｎは前記の意味を有する
ことができる。以下ウレタン及びクロル蟻酸エス
テルに係わる場合には、これ等両総合概念の下に
はチオノ、チオ及びジチオウレタン、並びにクロ
ル蟻酸チオノエステル、クロル蟻酸チオエステル
及びクロル蟻酸ジチオエステルも包含されるもの
とする。
前示された反応式より原料物質間の相互の関係
は極めて明らかである。更に置換基Ａ，Ｂ，Ｄ，
Ｅ，R1，R2，R3，R4及びＸの性質に応じて並び
に夫々の反応干与体の利用性に応じて一方又は他
方の方法が有利であることも明らかである。
公知のメターニトラニリン(A)より出発してメタ
―ニトロフエニルイソ（チオ）シアナート(B)が製
造され（W.Siefken，J.Liebigs Annalen der
Chemie第562巻第75頁及び夫以下1949年）、この
もの自体は成分R3―BHと円滑に反応してニトロ
（チオ）ウレタン(C)を生じ（S.Petersen in
Methoden der Crgan.Chemie，第巻第131頁、
Georg Thieme―Verlag，Stuttgart，第４版1952
年）、これは勿論直接メタ―ニトラニリン(A)とク
ロル蟻酸エステル（R3B―CA―Cl）とより（独
乙連邦共和国特許公開公報第1643763号）、又は二
硫化炭素或はオキシ硫化炭素、塩基及びアルキル
化剤とより（Methoden der Organischen
Chemie.第巻第831頁及び夫以下、Georg
Thieme―Verlag，Stuttgart，第４版1955年）も
得られる。次の還元はアミノ化合物（Ｆ，R2＝
Ｈ）を生じ（S.Schrｏ¨ter in Methoden der
Organischen Chemie，第XI／１巻第360頁及び
夫以下、Georg Thieme―Verlag，Stuttgart，第
４版1957年）これは直接又はアミノ窒素に於てモ
ノ置換された生成物に変じた後（Ｆ，R2＝Ｈ）
（Methoden der Organischen Chemie，第XI／
１巻、第24頁及び夫以下、Georg―Thieme―
Verlag，Stuttgart第４版1957年）クロル蟻酸エ
ステル（R4D―CE―Cl）（独乙連邦共和国特許公
開公告第1643763号）と、又は二硫化炭素或はオ
キシ硫化炭素、塩基及びアルキル化剤と反応せし
められて（Methoden der Organischen
Chemie，第巻第831頁及び夫以下、Georg―
Thieme―Verlag，Stuttgart，第４版1955年）所
望のジウレタン(H)を生ずる。しかもアミノウレタ
ン(F)はメタ―フエニレンジアミン(D)をクロル蟻酸
エステルと反応せしめることに依ても得られる。
更に他の合成可能性はアリール―１，３―ジイソ
（チオ）シアナート(E)をイソ（チオ）シアナトウ
レタン(G)に導く成分R3―BH1モルのみと反応せ
しめる点に存し（J.A.Parker，J.J.Thomas及び
C.L.Zeise，J.Org.Chem、第22巻第594乃至596頁
1957）、これ等はアミノウレタン(F)のチオフオス
ゲン化に依ても得られる（独乙連邦共和国特許公
開公報第1914270号第５頁例８）。続行の成分R4
―DHとの反応は所望の最終生成物を生ずる。原
則的に言うならば―CABR3或は―CEDR4基の順
序は任意である。
次に有利な合成ステツプを更に詳細に説明す
る：
(a) ３―ニトロフエニルイソ（チオ）シアナート
(B)の反応はイソ（チオ）シアナート反応に対し
て慣用の触媒例えば第３級アミン（トリエチル
アミン、１，４―ジアザビシクロ―（２，２，
２）―オクタン）、窒素含有複素環式化合物
（ピリジン、１，２―ジメチルイミダゾール）
又は有機錫化合物（ジブチル錫ジアセタート、
ジメチル錫ジクロリド）を使用し又は使用せず
に、場合に依り反応条件下にて不活性の溶剤例
えば炭化水素（リグロイン、ベンジン、トルオ
ール、ペンタン、シクロヘキサン）、ハロゲン
化炭化水素（メチレンクロリド、クロロフオル
ム、ジクロルエタン、クロルベンゾール，ｏ
―，ｍ―又はｐ―ジクロルベンゾール）、ニト
ロ炭化水素（ニトロベンゾール、ニトロメタ
ン）、ニトリル（アセトニトリル、ブチロニト
リル、ベンゾニトリル）、エーテル（ジエチル
エーテル、テトラヒドロフラン、ジオキサ
ン）、エステル（醋酸エチルエステル、プロピ
オン酸メチルエステル）、ケトン（アセトン、
メチルエチルケトン）又はアミド（ジメチルフ
オルムアミド、フオルムアミド）（独乙連邦共
和国特許公開公報第1568138号）中にて０乃至
150℃の範囲殊に40乃至100℃の範囲の温度に於
て行われる。
(b) ３―ニトラニリン(A)をクロル蟻酸エステルと
適当な溶剤例えば水、アルコール（メタノー
ル、エタノール、イソプロパノール）又は(a)に
記載したように普通の酸結合剤例えば水酸化ア
ルカリ、炭酸アルカリ、重炭酸アルカリ、酸化
アルカリ土類、水酸化アルカリ土類、炭酸アル
カリ土類、重炭酸アルカリ土類、第３級有機塩
基（例えばトリエチルアミン、ピリジン、Ｎ，
Ｎ―ジメチルアニリン、Ｎ，Ｎ―ジメチルシク
ロヘキシルアミン、キノリン、トリブチルアミ
ン）の助けに依り、又は原料物質３―ニトラニ
リンを−20乃至150℃殊に20乃至80℃の範囲の
温度に於て反応せしめられる。
(c) ニトロウレタン(C)の還元は公知の方法の１つ
に依り、例えば接触的水素添加に依り、金属―
酸組合せ例えば組合せ鉄―酸に依り、金属―ア
ルコール―組合せ例えば亜鉛末―水性アルコー
ル、鉄―水性アルコールに依り行われるとがで
きる。
(d) ｍ―フエニレンジアミン(D)の反応に対しては
(b)に対するような比較可能の条件が該当する
が、過剰のｍ―フエニレンジアミンにて操作す
るのが有利なこともある。
(e) アミノウレタン(E)とクロル蟻酸エステルとの
反応は(b)と同様にして行われるが、この場合例
えばニトロウレタン(C)の水素添加に依り得られ
る溶液も更に精製することなしに直接使用され
ることができる。
次の諸例は新規のジウレタン及びその前生成物
の製造を説明するものである：
ニトロウレタン
例 Ａ
４―クロルベンゾール64.3重量部及びトリエチ
ルアミン３重量部をトルオール（無水）430重量
部中に溶解せる溶液に、20乃至25℃に於て撹拌し
つつ、３―ニトロフエニルイソシアナート85重量
部乃びトルオール（無水）43重量部の混合物を添
加調合した。
反応を完全ならしめるために１時間室温に於て
後撹拌する。０℃に冷却せる後反応生成物を吸引
濾別する：
熔融点137乃至138℃
化合物は次の構造式を有する：
例 Ｂ
テトラヒドロフラン（THF）500重量部中に於
けるｍ―ニトラニリン138重量部に重炭酸ナトリ
ウム87重量部を添加する。撹拌しつつ室温に於て
クロル蟻酸チオメチルエステル120重量部を滴加
し、16時間室温に於て後撹拌し、濾過し、溶剤を
回転蒸発器に於て溜別し且つ得られる油状物質を
トルオール中に撹拌混入する。分離する結晶を吸
引濾別し且つ乾燥する：
熔融点137−138℃。
化合物は次の構造式を有する：
例 Ｃ
醋酸エチルエステル320重量部中に於ける３―
ニトロ―Ｎ―メチルアニリン26重量部に重炭酸ナ
トリウム17.4重量部を添加する。撹拌しつつ徐々
にクロル蟻酸―ｍ―トリエステル33重量部を添加
し、20時間室温に於て撹拌し、濾過し、溶剤を真
空中にて除去し且つ残留する残滓をトルオール／
シクロヘキサンより再結晶せしめる。熔融点114
乃至116℃。
化合物は次の構造式を有する：
相当する方法に依り次のニトロウレタン(C)が製
造されることができる：[Formula], Z is always different from Y, and R 1 and R 2 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, having 2 to 4 carbon atoms R 3 and R 4 are each, independently of each other, 1 to 4 substituted with unsubstituted alkyl having 1 to 6 carbon atoms or halogen or with alkoxy having 1 to 2 carbon atoms or with halogen or unsubstituted phenyl; from 5 to 8 carbon atoms optionally substituted by alkoxy having from 2 to 4 carbon atoms, alkenyl from 2 to 4 carbon atoms, alkynyl from 3 to 4 carbon atoms, alkyl from 1 to 4 carbon atoms; cycloalkyl with 7 to 8 carbon atoms, tricycloalkyl with 10 to 15 carbon atoms, phenyl rings with fused ring systems, phenyl, singly or multiply substituted phenyl, together with substituents alkyl having 1 to 4 carbon atoms, halogen, or alkoxy having 1 to 3 carbon atoms, and X is hydrogen, alkyl having 1 to 4 carbon atoms, halogen having 1 to 3 carbon atoms alkyl, alkoxy having 1 to 2 carbon atoms, halogen, nitro, or amino, n
is 1 to 4, and A, B, D, and E are each independently oxygen or sulfur, in which case all residues A, B, D, and E cannot be oxygen at the same time. , and at least one of these residues always represents sulfur) has a good herbicidal action against a number of major undesirable plants and at the same time a good herbicidal action on many cultivated plants. It is known to have good tolerability. These effects are better than those of known active substances. New compounds can be produced, for example, by the following method, in which residues A, B, D, ER,
R 1 , R 2 , R 3 .R 4 , X and n can have the meanings given above. In the following, when referring to urethane and chloroformate, these general concepts include thiono, thio, and dithiourethane, as well as chloroformate thionoester, chloroformate thioester, and chloroformate dithioester. From the reaction formula shown above, the mutual relationship between the raw materials is very clear. Furthermore, substituents A, B, D,
It is also clear that one or the other method may be advantageous depending on the nature of E, R 1 , R 2 , R 3 , R 4 and X and on the availability of the respective reaction donor. Meta-nitrophenyl iso(thio)cyanate (B) was prepared starting from the known meta-nitraniline (A) (W. Siefken, J. Liebigs Annalen der
Chemie Vol. 562, p. 75 and Husband et al. 1949), which itself reacts smoothly with component R 3 -BH to form nitro(thio)urethane (C) (S. Petersen in 1949).
Methoden der Crgan.Chemie, Volume No. 131,
Georg Thieme—Verlag, Stuttgart, 4th edition 1952
), this can, of course, be directly prepared by meta-nitraniline (A) and chloroformate (R 3 B-CA-Cl) (German Patent Publication No. 1643763), or by carbon disulfide or carbon oxysulfide. , base and alkylating agent (Methoden der Organischen)
Chemie. Vol. 831 and Husband, Georg
Thieme-Verlag, Stuttgart, 4th edition 1955) is also available. The next reduction is an amino compound (F, R 2 =
H) results in (S. Schroter in Methoden der
Organischen Chemie, Vol. R2 =H)
(Methoden der Organischen Chemie, Chapter XI/
Volume 1, page 24 and below, Georg-Thieme-
Verlag, Stuttgart 4th edition 1957) chloroformate (R 4 D-CE-Cl) (German Patent Publication No. 1643763), or carbon disulfide or carbon oxysulfide, a base and an alkylating agent. (Methoden der Organischen)
Chemie, Vol. 831, and my husband, George.
Thieme-Verlag, Stuttgart, 4th edition 1955) yields the desired diurethane (H). Furthermore, aminourethane (F) can also be obtained by reacting meta-phenylenediamine (D) with chloroformate.
Yet another synthetic possibility consists in reacting aryl-1,3-diiso(thio)cyanato (E) with only 1 mole of component R 3 -BH leading to iso(thio)cyanatourethane (G) (JAParker , JJThomas and
CLZeise, J.Org.Chem, Vol. 22, pp. 594-596.
1957), these can also be obtained by thiophosgenation of aminourethane (F) (Example 8, German Patent Publication No. 1914270, page 5). Continue component R 4
-Reaction with DH yields the desired final product. In principle, the order of the three CABR or four CEDR groups is arbitrary. The following advantageous synthetic steps are explained in more detail: (a) 3-nitrophenyliso(thio)cyanate
Reaction (B) is carried out using catalysts customary for iso(thio)cyanate reactions such as tertiary amines (triethylamine, 1,4-diazabicyclo-(2,2,
2)-octane), nitrogen-containing heterocyclic compounds (pyridine, 1,2-dimethylimidazole)
or organotin compounds (dibutyltin diacetate,
optionally with or without the use of solvents inert under the reaction conditions, such as hydrocarbons (ligroin, benzine, toluol, pentane, cyclohexane), halogenated hydrocarbons (methylene chloride, chloroform, dichloroethane, chlorobenzole, o
-, m- or p-dichlorobenzole), nitrohydrocarbons (nitrobenzole, nitromethane), nitriles (acetonitrile, butyronitrile, benzonitrile), ethers (diethyl ether, tetrahydrofuran, dioxane), esters (acetic acid ethyl ester, propionic acid) methyl ester), ketone (acetone,
methyl ethyl ketone) or amide (dimethyl formamide, formamide) (Federal Republic of Germany Patent Publication No. 1568138).
It is carried out at a temperature in the range of 150°C, especially in the range of 40 to 100°C. (b) 3-Nitraniline (A) is mixed with a chloroformate and a suitable solvent such as water, an alcohol (methanol, ethanol, isopropanol) or a common acid binder as described in (a) such as an alkali hydroxide, alkali carbonate, Alkali bicarbonates, alkaline earth oxides, alkaline earth hydroxides, alkaline earth carbonates, alkaline earth bicarbonates, tertiary organic bases (e.g. triethylamine, pyridine, N,
N-dimethylaniline, N,N-dimethylcyclohexylamine, quinoline, tributylamine) or by reacting the raw material 3-nitraniline at temperatures in the range -20 to 150°C, especially 20 to 80°C. It will be done. (c) The reduction of the nitrourethane (C) can be carried out by one of the known methods, for example by catalytic hydrogenation.
Acid combinations can be carried out, for example iron-acid combinations, metal-alcohol combinations such as zinc dust-aqueous alcohol, iron-aqueous alcohol. (d) For the reaction of m-phenylenediamine (D)
Comparable conditions as for (b) apply, but it may be advantageous to operate with an excess of m-phenylenediamine. (e) The reaction of aminourethane (E) with chloroformate is carried out analogously to (b), but in this case the solution obtained, for example, by hydrogenation of nitrourethane (C), is also reacted without further purification. Can be used directly. The following examples illustrate the preparation of novel diurethanes and their precursors: Nitrourethane Example A 64.3 parts by weight of 4-chlorobenzole and 3 parts by weight of triethylamine are dissolved in 430 parts by weight of toluene (anhydrous). A mixture of 85 parts by weight of 3-nitrophenyl isocyanate and 43 parts by weight of toluene (anhydrous) was added to the solution while stirring at 20 to 25°C. Stirring is continued for 1 hour at room temperature in order to complete the reaction. After cooling to 0° C., the reaction product is filtered off with suction: melting point 137-138° C. The compound has the following structural formula: Example B 87 parts by weight of sodium bicarbonate are added to 138 parts by weight of m-nitraniline in 500 parts by weight of tetrahydrofuran (THF). 120 parts by weight of chloroformic acid thiomethyl ester are added dropwise at room temperature with stirring, the mixture is stirred for 16 hours at room temperature, filtered, the solvent is distilled off in a rotary evaporator and the oil obtained is Stir into toluene. The crystals that separate are filtered off with suction and dried: melting point 137-138°C. The compound has the following structural formula: Example C 3- in 320 parts by weight of acetic acid ethyl ester
17.4 parts by weight of sodium bicarbonate are added to 26 parts by weight of nitro-N-methylaniline. 33 parts by weight of chloroformic acid-m-triester are slowly added with stirring, stirred at room temperature for 20 hours, filtered, the solvent removed in vacuo and the remaining residue dissolved in toluene/m-triester.
Recrystallize from cyclohexane. Melting point 114
〜116℃. The compound has the following structural formula: The following nitrourethanes (C) can be prepared by a corresponding method:
【表】【table】
【表】【table】
【表】【table】
【表】
アミノウレタン
例 Ｄ
Ｎ―（３―ニトロフエニル）―カルバミン酸―
４―クロルフエニルエステル135重量部をテトラ
ヒドロフラン（無水）900重量部中に溶解せる溶
液を水素添加触媒（獣炭上に於けるパラジウム10
％）３重量部と混和し、且つ室温及び0.02バール
H2圧に於て不変になるまで水素添加する。処理
するために触媒より分離され且つMgSO4にて乾
燥された溶液を結晶性反応生成物が良好に吸引濾
別されるに至るまで溶剤より分離した：186−187
℃。
構造式：
例 Ｅ
ｍ―フエニレンジアミン108重量部を水1000重
量部中に溶解せる溶液に、激しく撹拌しつつ極め
て徐々にクロル蟻酸フエニルエステル25.2重量部
を滴加する。反応終了後吸引濾別し、固状物質を
多数回稀塩酸にて洗滌し、合併せる酸性溶液をア
ンモニアにて中和し且つ吸引濾別する。斯しくて
得たる乾燥生成物は178乃至180℃に於て分解下に
熔融する。
構造式：
例 Ｆ
テトラヒドロフラン600重量部中に於ける２，
４―ジアミノニトロベンゾール51重量部及び重炭
酸ナトリウム43重量部に、激しく撹拌しつつ徐々
にクロル蟻酸フエニルエステル52.1重量部を滴加
する。14時間撹拌せる後濾過し、テトラヒドロフ
ランにて後洗滌する。結晶性粗製生成物が良好に
吸引されるに至るまで溶液を溶剤より分離し、ジ
エチルエーテルにて洗滌し且つ乾燥せる後物質は
223乃至225℃に於て熔融する。NMRスペクトル
及び元素分析に依れば物質は次の構造式を有す
る：
例 Ｇ
鉄粉末33重量部、アルコール75重量部、水60重
量部及び濃塩酸３重量部よりの80℃に加熱された
混合物に、激しく撹拌しつつ３（Ｓ―メチルチオ
カルバモイル）―ニトロベンゾール40重量部を、
温度が追加的加熱なしに80℃に保持されるような
部分にて添加する。次になお１時間還流しつつ煮
沸し、熱状態にて吸引濾別し、残滓を浸漬し、且
つ濾液をメチレンクロリド約1000重量部にて硫酸
ナトリウム上にて乾燥し、濃縮し且つトルオール
より再結晶せしめる：熔融点101乃至103℃。
構造式：
相当する方法に依り次のアミノウレタン(F)が製
造されることができる：[Table] Aminourethane examples D N-(3-nitrophenyl)-carbamic acid-
A solution of 135 parts by weight of 4-chlorophenyl ester dissolved in 900 parts by weight of tetrahydrofuran (anhydrous) was prepared using a hydrogenation catalyst (palladium-10 on animal charcoal).
%) 3 parts by weight and at room temperature and 0.02 bar
Hydrogenate until constant under H 2 pressure. For treatment, the solution was separated from the catalyst and dried with MgSO 4 and separated from the solvent until the crystalline reaction product was successfully filtered off with suction: 186-187
℃. Structural formula: Example E To a solution of 108 parts by weight of m-phenylenediamine dissolved in 1000 parts by weight of water, 25.2 parts by weight of phenyl chloroformate are added dropwise very slowly with vigorous stirring. After the reaction is complete, it is filtered off with suction, the solid material is washed several times with dilute hydrochloric acid, the combined acidic solution is neutralized with ammonia and filtered off with suction. The dry product thus obtained melts with decomposition at 178-180°C. Structural formula: Example F 2, in 600 parts by weight of tetrahydrofuran
52.1 parts by weight of chloroformic acid phenyl ester are gradually added dropwise to 51 parts by weight of 4-diaminonitrobenzole and 43 parts by weight of sodium bicarbonate with vigorous stirring. After stirring for 14 hours, it is filtered and washed with tetrahydrofuran. After separating the solution from the solvent, washing with diethyl ether and drying until the crystalline crude product was well aspirated, the material was
Melts at 223-225°C. According to NMR spectrum and elemental analysis, the substance has the following structural formula: Example G Add 40 parts by weight of 3(S-methylthiocarbamoyl)-nitrobenzole to a mixture heated to 80°C of 33 parts by weight of iron powder, 75 parts by weight of alcohol, 60 parts by weight of water and 3 parts by weight of concentrated hydrochloric acid with vigorous stirring. Department,
Addition is made in such a way that the temperature is maintained at 80° C. without additional heating. It is then boiled under reflux for another hour, filtered off hot with suction, the residue is soaked, and the filtrate is dried over sodium sulfate with about 1000 parts by weight of methylene chloride, concentrated and reconstituted from toluene. Crystallization: Melting point 101-103℃. Structural formula: The following aminourethanes (F) can be prepared by a corresponding method:
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
ジウレタン
例 １
Ｎ―（３―アミノフエニル）―カルバミン酸フ
エニルエステル22.8重量部をテトラヒドロフラン
（無水）200重量部中に溶解せる溶液に重炭酸ナト
リウム11重量部を添加し、続いて冷却下20乃至25
℃に於てクロル蟻酸チオメチルエステル13.3重量
部を添加調合する。反応を完全ならしめるために
１時間室温に於て撹拌する。続いて反応混合物を
濾過し且つ濾液を真空中にて濃縮する。油状残滓
をトルオールの添加に依り結晶せしめた。熔融点
155−157℃（第１号）。化合物は次の構造式を有
する：
例 ２
Ｎ―（３―イソチオシアナトフエニル）―０―
メチルカルバマート〔Ｎ―（３―アミノフエニ
ル）―０―メチルカルバマート及びチオフオスゲ
ンより得られる。熔融点99〜100℃〕20重量部、
メタノール20重量部、トリエチルアミン３重量部
及びトルオール150重量部よりの混合物を６時間
沸騰加熱する。濃縮後トルオールより再結晶せし
める：熔融点147−149℃（第２号）。化合物は次
の構造式を有する：
例 ３
Ｎ（３―アミノフエニル）―０―メチルウレタ
ン16.6重量部及びトリエチルアミン10.1重量部を
ジエチルエーテル300重量部中に溶解せる溶液
に、室温に於て二硫化炭素10重量部を滴加する。
残滓を水120重量部中に懸濁し、且つ撹拌しつつ
ジエチルスルフアート9.1容量部と混和する。20
時間撹拌せる後吸引濾別し、水に洗滌し且つ空気
中にて乾燥する：熔融点122−124℃（第３号）。
化合物は次の構造式を有する：
相当する方法にて次の化合物が製造されること
ができる：[Table] Diurethane Example 1 To a solution of 22.8 parts by weight of N-(3-aminophenyl)-carbamic acid phenyl ester dissolved in 200 parts by weight of tetrahydrofuran (anhydrous), 11 parts by weight of sodium bicarbonate were added, followed by cooling. 20 to 25
13.3 parts by weight of chloroformic acid thiomethyl ester was added and prepared at ℃. Stir at room temperature for 1 hour to complete the reaction. The reaction mixture is subsequently filtered and the filtrate is concentrated in vacuo. The oily residue was crystallized by addition of toluene. melting point
155-157℃ (No. 1). The compound has the following structural formula: Example 2 N-(3-isothiocyanatophenyl)-0-
Methyl carbamate [obtained from N-(3-aminophenyl)-0-methyl carbamate and thiophosgene. Melting point 99-100℃〕20 parts by weight,
A mixture of 20 parts by weight of methanol, 3 parts by weight of triethylamine and 150 parts by weight of toluene is heated to boiling for 6 hours. After concentration, recrystallize from toluene: melting point 147-149°C (No. 2). The compound has the following structural formula: Example 3 10 parts by weight of carbon disulfide are added dropwise at room temperature to a solution of 16.6 parts by weight of N(3-aminophenyl)-0-methylurethane and 10.1 parts by weight of triethylamine in 300 parts by weight of diethyl ether.
The residue is suspended in 120 parts by weight of water and mixed with 9.1 parts by volume of diethyl sulfate with stirring. 20
After stirring for an hour, it is filtered off with suction, washed with water and dried in air: melting point 122-124°C (No. 3).
The compound has the following structural formula: The following compounds can be prepared in a corresponding manner:
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
次の試験に対しては公知の除草有効物質が比較
のために干与せしめられた。メチル―Ｎ―（３―
N′―（3′―メチルフエニル―カルバモイル）―フ
エニル）―カルバマート及びエチル―Ｎ―
（N′―フエニルカルバモイルオキシ）―フエニ
ル）―カルバマート（独乙連邦共和国特許公告公
報第1567151号）は、そのフダンソウに対し注目
に値する程度の忍容性に於て、望ましからぬ濶葉
植物に対する著しく異なる作用に依て優れてい
る。然し乍らこの場合には公知のように差異を記
録しなければならない。何となればメチル―Ｎ―
（３―（N′―（3′―メチルフエニルカルバモイル
オキシ）―フエニル）―カルバマートは、このタ
イプの前記第２の化合物よりもなお有利なこの栽
培植物に於ける選択性を有するからである。３―
イソプロピル―２，１，３―ベンゾチアジアジノ
ン―(4)―２，２―ジオキシド（独乙連邦共和国特
許公告公報第1542836号）は全く異なる使用範囲
を有する。この化合物にて大豆、落花生、穀物、
玉蜀黍及び若干の野菜類中に於ける種々の濶葉雑
草が撲滅された。然し乍らこの場合にはなお作用
隙間が存在していた。メチル―Ｎ―（３―N′―
メチル―N′―フエニル―カルバモイルオキシ）
―フエニル）―カルバマートは、その級に対する
良好な除草作用に於て栽培植物選択性を殆んど示
さない。そのためにこの化合物は例えば大豆に対
しては下葉吹きつけに対してのみ推奨されたに過
ぎなかつた（Arndt，F.and G.Boroschewsky：
New Selective Herbicides―International
Plant Protection Congress，Reports and
Information，Section Chemical Control，
Part，Moskow 1975年第42−49頁）。この場合
栽培植物の若い芽部分及び葉は噴射液に依ては当
てられずに、これ等の下に存在する望ましからぬ
植物だけが当てられるようにしなければならな
い。
新規の硫黄含有ジウレタンの除草作用に対する
例
多数の試験結果は新規の化合物の良好な除草性
質を証明する。試験結果はその除草能及びその栽
培植物中に於ける選択性に関し、次の試験に依る
生物学的作用に依り特徴づけられている：
温室試験
内容300cm3のプラスチツク植木鉢に粘土質砂土
を充填し、且つ試験植物を種類に依て分けて植付
けた。この場合は主として種子のまきつけ又は植
物的に増殖た種類に於ける移植に係る。有効物質
は分布剤として水中に懸濁又は乳濁され、且つ細
分布ノズルに依り発芽後使用に於て試験植物の葉
及びなお裸のままの土地表面上に吹きつけられ
た。葉処理のために植物を生長形に応じて試験容
器中に於て３乃至10cmの高さまで栽培し、次にこ
れを処理した。試験植物の温度要求には、試験植
物を温室設備の比較的冷たい区分又は比較的暖か
い区分に配置することに依り答えた。試験期間は
２乃至４週間続いた。この期間中植物を栽培し且
つその個々の処理に対する反応を評価した。試験
物質の使用量は１ヘクタール当りの有効物質のKg
となつている。評価のために０乃至100の規準が
役立つた。この場合０は損傷なしを意味し、100
は植物の枯死を意味する。
結 果
添附の表中の番号にて表示の材料は栽培植物及
び望ましからぬ植物の発芽後の葉処理に際しての
有効物質の作用を説明するものである（表２乃至
12）。この場合注目すべきことは、新規の化合物
が除草活性度及び作用スペクトルに関し比較剤と
して干与せしめられたジウレタンに比し優れてい
る点である。然し乍ら栽培植物に対する選択性に
於ける主要点は相違する。このことは例えば大豆
及び穀物に於ては完全に示される。これ等栽培植
物に於ては、公知の３―イソプロピル―２，１，
３―ベンゾチアジアジノン―(4)―２，２―ジオキ
シドに同等である忍容度が達成される（表５，
６）。その外にその余裕が正に本発明に依る化合
物に対して際立つており、これに反し試験された
比較剤が不適当である一列の栽培植物が存在する
（表２，４，５）。
適用方法としては、勿論土中への埋入又は土地
表面の処理が考慮されることができるが、発芽し
た植物の処理が殊に有利である。特殊使用例えば
葉下吹きつけも考慮される。この場合には発芽し
た敏感な栽培植物の葉にはできるだけ当らない
で、剤がその下に在る土地表面又はそこに生長し
ている望ましからぬ植物上に達するように噴射流
が指向される。
適用方法の多方面性を考慮して本発明に依る剤
又はこれを含有する混合物は、表中に挙げられた
有用植物に於ける外に、更に多数の栽培植物に於
て望ましからぬ植物成長を阻止するために使用さ
れることができる。この場合使用濃度は撲滅対象
物に応じて１ヘクタールにつき0.1乃至15Kgであ
ることができる。
詳細には次の有用植物が挙げられる：
タマネギ（Allium cepa）
パイナツプル（Ananas comosus）
アスパラガス（Asparagus officinalis）
オートムギ（Avena sativa）
フダンソウ（Beta vulgaris spp.altissima）
サトウジシヤ（Beta vulgaris spp.rapa）
アカテンサイ（Beta vulgaris spp.esculenta）
ブラシーカ ナパス（変種 ナパス）（Brassica
napus var.napus）
ブラシーカ ナパス（変種 ナポブラシーカ）
（Brassica napus var.napobrassica）
ブラシーカ ナパス（変種 ラパ）（Brassica
napus var.rapa）
ブラシーカ ナパス（変種 シルベストリス）
（Brassica rapa var.silvestris）
トウツバキ（Camellia sinensis）
マルブシユカン（Citrus limon）
グレープフルーツ（Citrus maxima）
ダイダイ（Citrus reticulata）
ナツミカン（Citrus sinensis）
コーヒーノキ〔Coffea arabica （Coffea
canephora.Coffea liberica）〕
アミメロン（Cucumis melo）
キユウリ（Cucumis sativus）
ギヨウギシバ（Cynodon dactylon）
アブラヤミ（Elaeis guineensis）
イチゴ（Fragaria vesca）
木綿〔Gossypium hirsutum）
（Gossypium arboreum
Gossypium herbaceum
Gossypium vitifolium）〕
ヒマワリ（Helianthus annuus）
キクイモ（Helianthus tuberosus）
ゴムノキ（Hevea brasiliensis）
大麦（Hordeum vulgare）
カラハナソウ（Humulus lupulus）
アメリカイモ（lpomoea batatas）
ニガナ（Lactuca sativa）
レンズマメ（Lens culinaris）
アマ（Linum usitatissimum）
トマト（Lycopersicon lycopersicum）
リンゴ属（Malus spp.）
キヤツサバ（Manihot esculenta）
ムラサキウマゴヤシ（Medicago sativa）
ハツカ（Mentha piperita）
バシヨウ（Musa spp.）
タバコ〔Nicotiana tabacum（N.rustica）〕
オリーブ（Olea europaea）
イネ（Oryza sativa）
キビ（Panicum miliaceum）
アズキ（Phaseolus lunatus）
ササゲ（Phaseolus mungo）
ゴガツササゲ（Phaseolus vulgaris）
パセリ（Pennisetum glaucum）
（Petroselinum crispumspp.tuberosum）
トウヒ（Picea abies）
モミ（Abies alba）
マツ属（Pinus spp.）
シロエンドウ（Pisum sativum）
サクラ（Prunus avium）
アンズ（Prunus domestica）
モモ（Prunus persica）
ナシ（Pyrus communis）
サグリ（Ribes sylvestre）
サンザシ（Ribes uva―crispa）
トウゴマ（Ricinus communis）
サトウキビ（Saccharum officinarum）
ライムギ（Secale cereale）
ゴマ（Sesamum indicum）
ジヤガイモ（Solanun tuberosum）
モロコシ〔Sorghum bicolor（s.vulgare）〕
モロコシガヤ（Sorghum dochna）
ホウレンソウ（Spinacia oleracea）
カカオノキ（Theobroma cacao）
ムラサキツユクサ（Trifolium pratense）
イワツツジ（Vaccinium corymbosum）
コケモモ（Vaccinium vitis―idaea）
ソラマメ（Vicia faba）
ササゲ（Vigna sinensis）（V.unguiculata）
ブドウ（Vitis vinifera）
新規の個々の作用スペクトルを更に拡大するた
めに、相乗効果を達成するために又は土地上に於
ける残留作用を改善するために、新規の化合物は
互に混合され、又は多数の他の除草性又は生長制
御性化合物が混合又は組合せパートナーとして使
用されることができる。使用領域及び撲滅計画に
応じて次の化合物又は化学的に類似の誘導体がパ
ートナーとして役立つ：[Table] For the following tests, known herbicidal active substances were dried for comparison. Methyl-N-(3-
N'-(3'-methylphenyl-carbamoyl)-phenyl)-carbamate and ethyl-N-
(N'-phenylcarbamoyloxy)-phenyl)-carbamate (German Patent Publication No. 1567151) has a remarkable degree of tolerability to Swiss chard, and has been shown to have an undesirable effect on chard. They are distinguished by their significantly different effects on plants. However, in this case the differences must be recorded in a known manner. What about methyl-N-?
(3-(N′-(3′-methylphenylcarbamoyloxy)-phenyl)-carbamate has an even more advantageous selectivity in this cultivated plant than said second compound of this type. .3-
Isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide (German Patent Publication No. 1542836) has a completely different range of use. This compound contains soybeans, peanuts, grains,
Various leafy weeds in corn and some vegetables have been eradicated. However, in this case there was still a working gap. Methyl-N-(3-N'-
methyl-N′-phenyl-carbamoyloxy)
-Phenyl)-carbamates exhibit little plant selectivity in their good herbicidal action against their class. This compound was therefore only recommended for under-leaf spraying, for example on soybeans (Arndt, F. and G. Boroschewsky:
New Selective Herbicides―International
Plant Protection Congress, Reports and
Information, Section Chemical Control,
Part, Moscow 1975, pp. 42-49). In this case, it must be ensured that the young shoots and leaves of the cultivated plants are not exposed to the spray, but only the undesirable plants located beneath them. Example for the herbicidal action of the new sulfur-containing diurethanes Numerous test results demonstrate the good herbicidal properties of the new compounds. The test results, regarding its herbicidal ability and its selectivity in cultivated plants, are characterized by its biological action according to the following tests: Greenhouse test Description: 300 cm 3 plastic flower pots filled with clay sandy soil. The test plants were then planted according to type. This case mainly concerns sowing seeds or transplanting in vegetatively propagated varieties. The active substance was suspended or emulsified in water as a distribution agent and sprayed by means of a fine distribution nozzle onto the leaves of the test plants and the still bare soil surface in post-emergence application. For foliar treatment, plants were grown in test containers to a height of 3 to 10 cm, depending on the growth form, and then treated. The temperature requirements of the test plants were met by placing the test plants in either a cooler section or a warmer section of the greenhouse facility. The study period lasted from 2 to 4 weeks. Plants were grown during this period and their responses to individual treatments were evaluated. The amount of test substance used is Kg of active substance per hectare.
It is becoming. A scale of 0 to 100 was useful for evaluation. In this case 0 means no damage, 100
means the death of the plant. Results The materials indicated by numbers in the attached table illustrate the action of the active substances in post-emergence leaf treatment of cultivated and undesirable plants (Tables 2 and 3).
12). What is noteworthy in this case is the superiority of the new compounds in terms of herbicidal activity and spectrum of action compared to the dried diurethane used as a comparison agent. However, the key points in selectivity for cultivated plants are different. This is perfectly demonstrated in soybeans and grains, for example. In these cultivated plants, the known 3-isopropyl-2,1,
Tolerability comparable to that of 3-benzothiadiazinone-(4)-2,2-dioxide is achieved (Table 5,
6). In addition, there is a row of cultivated plants whose margins are particularly pronounced for the compounds according to the invention, and for which the comparative agents tested are unsuitable (Tables 2, 4, 5). As a method of application, of course, embedding in the soil or treatment of the land surface can be considered, but treatment of germinated plants is particularly advantageous. Special uses such as under-leaf spraying are also considered. In this case, the jet stream is directed in such a way that it reaches the underlying soil surface or the undesirable plants growing thereon, with as little as possible hitting the leaves of germinated sensitive cultivated plants. Ru. Taking into account the versatility of application methods, the agent according to the present invention or the mixture containing the same can be used not only for the useful plants listed in the table, but also for a large number of undesirable cultivated plants. Can be used to inhibit growth. In this case, the concentration used can be from 0.1 to 15 kg per hectare, depending on the species to be eradicated. In detail, the following useful plants are mentioned: Onion (Allium cepa) Pineapple (Ananas comosus) Asparagus (Asparagus officinalis) Oat (Avena sativa) Chard (Beta vulgaris spp. altissima) Sugar beet (Beta vulgaris spp. rapa) Red beet ( Beta vulgaris spp.esculenta) Brassica (var. Napus) (Brassica
napus var.napus) Brassica napus (variety napus var.napus)
(Brassica napus var.napobrassica) Brassica napus (var. rapa) (Brassica
napus var.rapa) Brassica napus (var. sylvestris)
(Brassica rapa var.silvestris) Camellia sinensis Citrus limon Grapefruit (Citrus maxima) Citrus reticulata Jujube mandarin (Citrus sinensis) Coffea arabica (Coffea
canephora.Coffea liberica)] Canephora (Cucumis melo) Cucurbita (Cucumis sativus) Cynodon dactylon Elaeis guineensis Strawberry (Fragaria vesca) Cotton (Gossypium hirsutum) (Gossypium arboreum Gossypium herbaceum Gossypium vi tifolium)〕 Sunflower (Helianthus annuus) Jerusalem artichoke (Helianthus tuberosus) Rubber tree (Hevea brasiliensis) Barley (Hordeum vulgare) Humulus lupulus American potato (lpomoea batatas) Bittersweet (Lactuca sativa) Lentil (Lens culinaris) Linum (Linum usitatissimum) Tomato (Lycopersicon lycopersicum) Malus spp.) Manihot esculenta Medicago sativa Mentha piperita Musa spp. Tobacco (Nicotiana tabacum (N.rustica)) Olive (Olea europaea) Rice (Oryza sativa) Millet (Panicum miliaceum) Azuki (Phaseolus lunatus) Cowpea (Phaseolus mungo) Cowpea (Phaseolus vulgaris) Parsley (Pennisetum glaucum) (Petroselinum crispumspp.tuberosum) Spruce (Picea abies) Fir (Abies alba) Pinus spp. White pea (Pisum sativum) Cherry tree (Prunus avium) Apricot (Prunus domestica) Peach (Prunus persica) Pear (Pyrus communis) Currant (Ribes sylvestre) Hawthorn (Ribes uva-crispa) Castor (Ricinus communis) Sugarcane (Saccharum officinarum) Rye (Secale cereale) Sesame (Sesamum indicum) ) Solanun tuberosum Sorghum bicolor (s.vulgare) Sorghum dochna Spinach (Spinacia oleracea) Cocoa (Theobroma cacao) Trifolium pratense Vaccinium corymbosum Cowberry (Vaccinium vitis-ida) ea) Broad beans ( Vicia faba) Cowpea (Vigna sinensis) (V. unguiculata) Grapevine (Vitis vinifera) To further expand the spectrum of new individual actions, to achieve synergistic effects or to improve residual action on the land. Additionally, the novel compounds can be mixed with each other or a number of other herbicidal or growth-regulating compounds can be used as mixing or combination partners. Depending on the area of use and eradication program, the following compounds or chemically similar derivatives can serve as partners:
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
＝
O
[Table] =
O
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【表】【table】
【表】
合害虫又は植物病糸状菌又は細菌を撲滅する剤を
考えることができる。更に栄養又は稀有元素不足
を除くために使用される無機塩溶液との混合性も
重要である。
除草作用を活性化するために、湿潤剤、接着剤
並びに非植物毒性油を添加することができる。
使用は例えば直接飛散可能の溶液、粉末、懸濁
液又は分散液、乳濁液、油分散液、ペースト、振
りかけ剤、撒布剤、粒状体の形に於て飛散、噴
霧、振りかけ、撒布又は傾注に依り行われる。使
用形は完全に使用目的に適合せしめられる；使用
形は何れの場合にもできるだけ本発明に依る有効
物質の極めて細かい分布を保証しなければならな
い。
直接飛散可能の溶液、乳濁液、ペースト及び油
分散液を製造するために、中位乃至高位の沸点の
鉱油溜分例えば燈油又はデイーゼル油、更にコー
ルタール油等、並びに植物性又は動物性産出源の
油、脂肪族、環状及び芳香族炭化水素例えばベン
ゾール、トルオール、キシロール、パラフイン、
テトラヒドロナフタリン、アルキル置換ナフタリ
ン又はその誘導体、例えばメタノール、エタノー
ル、プロパノール、ブタノール、クロロフオル
ム、四塩化炭素、シクロヘキサノール、シクロヘ
キサノン、クロルベンゾール、イソフオロン等、
強極性溶剤例えばジメチルフオルムアミド、ジメ
チルスルフオキシド、Ｎ―メチルピロリドン、水
等が使用される。
水性使用形は乳濁液濃縮物、ペースト又は湿潤
可能の粉末（噴射粉末）、油分散液より水の添加
により製造されることができる。乳濁液、ペース
ト又は油分散液を製造するためには、物質はその
まま又は油又は溶剤中に溶解して、湿潤剤、接着
剤、分散剤又は乳化剤に依り水中に均質に混合さ
れることができる。然かも有効物質、湿潤剤、接
着剤、分散剤又は乳化剤及び場合に依り溶剤又は
油より成れる濃縮物を製造することもでき、これ
は水にて稀釈するのに適する。
表面活性物質としては次のものが挙げられる：
リグニンスルフオン酸、ナフタリンスルフオン
酸、フエノールスルフオン酸のアルカリ塩、アル
カリ土類塩、アンモニウム塩、アルキルアリール
スルフオナート、アルキルスルフアート、アルキ
ルスルフオナート、ジブチルナフタリンスルフオ
ン酸のアルカリ塩及びアルカリ土類塩、ラウリル
エーテルスルフアート、脂肪アルコールスルフア
ート、脂肪酸アルカリ塩及びアルカリ土類塩、硫
酸化ヘキサデカノール、ヘプタデカノール、オク
タデカノールの塩、硫酸化脂肪アルコールグリコ
ールエーテルの塩、スルフオン化ナフタリン又は
ナフタリン誘導体とフオルムアルデヒドとの縮合
生成物、ナフタリン或はナフタリンスルフオン酸
とフエノール及びフオルムアルデヒドとの縮合生
成物、ポリオキシエチレン―オクチルフエノール
エーテル、エトキシル化イソオクチルフエノール
―、オクチルフエノール―，ノニルフエノール
―，アルキルフエノールポリグリコールエーテ
ル、トリブチルフエニルポリグリコールエーテ
ル，アルキルアリールポリエーテルアルコール，
イソトリデシルアルコール、脂肪アルコールエチ
レンオキシド―縮合物、エトキシル化ヒマシ油、
ポリオキシエチレンアルキルエーテル，エトキシ
ル化ポリオキシプロピレン、ラウリルアルコール
ポリグリコールエーテルアセタール、ソルビツト
エステル、リグニン，亜硫酸廃液及びメチル繊維
素。
粉末、撒布剤及び振りかけ剤は有効物質と固状
担体物質とを混合又は一緒に磨砕することに依り
製造されることができる。
粒状体例えば被覆、透浸及び均質粒状体は、有
効物質を固状担体物質に結合することに依り製造
されることができる。固状担体物質は例えば鉱物
土例えばシリカゲル、珪酸、珪酸ゲル、珪酸塩，
滑石，カオリン，アタクレー，石灰石，石灰，白
亜，膠塊粒土，石灰質黄色粘土，粘土，白雲石；
珪藻土、硫酸カルシウム，硫酸マグネシウム，酸
化マグネシウム，磨砕合成樹脂，肥料例えば硫酸
アンモニウム，燐酸アンモニウム，硝酸アンモニ
ウム，尿素及び植物性生成物例えば穀物粉，樹
皮，木材及びクルミ殻粉，繊維素粉末及び他の固
状担体物質である。
使用形は有効物質0.1乃至95重量％殊に0.5乃至
90重量％を含有する。
例 ４
化合物２：90重量部をＮ―メチル―α―ピロリ
ドン10重量部と混合する時は、極めて小さい滴の
形にて使用するのに適する溶液が得られる。
例 ５
化合物８：20重量部を、キシロール80重量部，
エチレンオキシド８乃至10モルをオレイン酸―Ｎ
―モノエタノールアミド１モルに附加せる附加生
成物10重量部、ドデシルベンゾールスルフオン酸
のカルシウム塩５重量部及びエチレンオキシド40
モルをヒマシ油１モルに附加せる附加生成物５重
量部より成れる混合物中に溶解する。この溶液を
水100000重量部中に注入し且つ細分布することに
より、有効物質0.02重量％を含有する水性分散液
が得られる。
例 ６
化合物13：20重量部を、シクロヘキサノン40重
量部、イソブタノール30重量部、エチレンオキシ
ド７モルをイソオクチルフエノール１モルに附加
せる附加生成物20重量部及びエチレンオキシド40
モルをヒマシ油１モルに附加せる附加生成物10重
量部より成れる混合物中に溶解する。この溶液を
水100000重量部中に注入し且つ細分布することに
依り、有効物質0.02重量％を含有する水性分散液
が得られる。
例 ７
化合物23：20重量部を、シクロヘキサノール25
重量部、沸点210乃至280℃の鉱油溜分65重量部及
びエチレンオキシド40モルをヒマシ油１モルに附
加せる附加生成物10重量部より成れる混合物中に
溶解する。この溶液を水100000重量部中に注入し
且つ細分布することに依り、有効物質0.02重量％
を含有する水性分散液が得られる。
例 ８
有効物質７：20重量部を、ジイソブチル―ナフ
タリン―α―スルフオン酸のナトリウム塩３重量
部、亜硫酸―廃液よりのリグニンスルフオン酸の
ナトリウム塩17重量部及び粉末状珪酸ゲル60重量
部と充分に混和し、且つハンマーミル中に於て磨
砕する。混合物を水20000重量部中に細分布する
ことに依り、有効物質0.1重量％を含有する噴射
液が得られる。
例 ９
化合物46：３重量部を細粒状カオリン97重量部
と密に混和する。斯くして有効物質３重量％を含
有する噴霧剤が得られる。
例 10
化合物２：30重量部を粉末状珪酸ゲル92重量部
及びこの珪酸ゲルの表面上に吹きつけられたパラ
フイン油８重量部より成る混合物と密に混和す
る。斯くして良好な接着性を有する有効物質の製
剤が得られる。
例 11
有効物質７：40重量部をフエノールスルフオン
酸―尿素―フオルムアルデヒド―縮合物のナトリ
ウム塩10重量部、珪酸ゲル２重量部及び水48重量
部と密に混和する。安定な水性分散液が得られ
る。水100000重量部にて稀釈することに依り、有
効物質0.04重量％を含有する水性分散液が得られ
る。
例 12
有効物質８：20重量部をドデシルベンゾールス
ルフオン酸のカルシウム塩２重量部、脂肪アルコ
ール―ポリグリコールエーテル８重量部、フエノ
ールスルフオン酸―尿素―フオルムアルデヒド―
縮合物のナトリウム塩２重量部及びパラフイン系
鉱油68重量部と密に混和する。安定な油状分散液
が得られる。[Table] Agents for eradicating pests or plant-pathogenic fungi or bacteria can be considered. Furthermore, miscibility with inorganic salt solutions used to eliminate nutritional or rare element deficiencies is also important. Wetting agents, adhesives as well as non-phytotoxic oils can be added to activate the herbicidal action. The use may be, for example, in the form of directly splashable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, sprinkles, spreaders, granules, scattering, spraying, sprinkling, scattering or pouring. It is carried out depending on. The use form is perfectly adapted to the intended use; the use form must in each case ensure as fine a distribution of the active substance according to the invention as possible. For the production of directly splashable solutions, emulsions, pastes and oil dispersions, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, as well as coal tar oil, etc., as well as vegetable or animal products, can be used. source oils, aliphatic, cyclic and aromatic hydrocarbons such as benzol, toluol, xylol, paraffin,
Tetrahydronaphthalene, alkyl-substituted naphthalene or derivatives thereof, such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzole, isophorone, etc.
Strong polar solvents such as dimethyl formamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. are used. Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders), oil dispersions by addition of water. To produce emulsions, pastes or oil dispersions, the substances can be mixed homogeneously in water, either as such or dissolved in oil or solvents, by means of wetting agents, adhesives, dispersants or emulsifiers. can. It is also possible, however, to prepare concentrates consisting of the active substance, wetting agents, adhesives, dispersing agents or emulsifiers and, if appropriate, solvents or oils, which are suitable for dilution with water. Surface-active substances include:
Alkali salts of lignin sulfonic acid, naphthalene sulfonic acid, phenolsulfonic acid, alkaline earth salts, ammonium salts, alkylaryl sulfonates, alkyl sulfonates, alkyl sulfonates, alkali salts of dibutylnaphthalene sulfonic acid and alkaline earth salts, lauryl ether sulfate, fatty alcohol sulfate, fatty acid alkali salts and alkaline earth salts, salts of sulfated hexadecanol, heptadecanol, octadecanol, sulfated fatty alcohol glycol ethers. salts, condensation products of sulfonated naphthalene or naphthalene derivatives and formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid and phenol and formaldehyde, polyoxyethylene-octylphenol ether, ethoxylated isooctylphenol ―, octylphenol―, nonylphenol―, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohol,
Isotridecyl alcohol, fatty alcohol ethylene oxide condensate, ethoxylated castor oil,
Polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbit ester, lignin, sulfite waste liquor and methyl cellulose. Powders, sprays and sprinkles can be produced by mixing or milling together the active substance and a solid carrier material. Granules, such as coated, impregnated and homogeneous granules, can be produced by binding the active substance to solid carrier materials. Solid support materials include, for example, mineral earths such as silica gel, silicic acid, silicic acid gel, silicates,
Talc, kaolin, atakulay, limestone, chalk, chalk, agglomerate granular soil, calcareous yellow clay, clay, dolomite;
Diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic resins, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and vegetable products such as flour, bark, wood and walnut shell flour, cellulose powder and other solids. carrier material. The used form contains 0.1 to 95% by weight of active substance, especially 0.5 to 95% by weight.
Contains 90% by weight. Example 4 Compound 2: When 90 parts by weight are mixed with 10 parts by weight of N-methyl-α-pyrrolidone, a solution is obtained which is suitable for use in the form of very small drops. Example 5 Compound 8: 20 parts by weight, xylol 80 parts by weight,
8 to 10 moles of ethylene oxide to oleic acid-N
- 10 parts by weight of addition product added to 1 mole of monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzole sulfonic acid and 40 parts by weight of ethylene oxide
mol of castor oil is dissolved in a mixture consisting of 5 parts by weight of the adduct. By pouring this solution into 100,000 parts by weight of water and finely distributing it, an aqueous dispersion containing 0.02% by weight of active substance is obtained. Example 6 Compound 13: Addition product of 20 parts by weight, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 7 moles of ethylene oxide to 1 mole of isooctylphenol, and 40 parts by weight of ethylene oxide.
mol of castor oil is added to 1 mol of castor oil in a mixture consisting of 10 parts by weight of the addition product. By pouring this solution into 100,000 parts by weight of water and finely distributing it, an aqueous dispersion containing 0.02% by weight of active substance is obtained. Example 7 Compound 23: 20 parts by weight, cyclohexanol 25
parts by weight, 65 parts by weight of a mineral oil fraction with a boiling point of 210 DEG -280 DEG C. and 10 parts by weight of an adduct of 40 moles of ethylene oxide added to 1 mole of castor oil. By pouring this solution into 100,000 parts by weight of water and finely distributing it, 0.02% by weight of the active substance was obtained.
An aqueous dispersion containing . Example 8 Active substance 7: 20 parts by weight, 3 parts by weight of sodium salt of diisobutyl-naphthalene-α-sulfonic acid, 17 parts by weight of sodium salt of lignin sulfonic acid from sulfite waste liquid, and 60 parts by weight of powdered silicic acid gel. Mix thoroughly and grind in a hammer mill. By subdividing the mixture in 20,000 parts by weight of water, a propellant containing 0.1% by weight of active substance is obtained. Example 9 Compound 46: 3 parts by weight are intimately mixed with 97 parts by weight of finely divided kaolin. A propellant containing 3% by weight of active substance is thus obtained. Example 10 Compound 2: 30 parts by weight are intimately mixed with a mixture consisting of 92 parts by weight of powdered silicic acid gel and 8 parts by weight of paraffin oil which is sprayed onto the surface of this silicic acid gel. Active substance formulations with good adhesive properties are thus obtained. Example 11 Active substance 7: 40 parts by weight are intimately mixed with 10 parts by weight of the sodium salt of phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silicic acid gel and 48 parts by weight of water. A stable aqueous dispersion is obtained. By diluting with 100,000 parts by weight of water, an aqueous dispersion containing 0.04% by weight of active substance is obtained. Example 12 Active substance 8: 20 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol-polyglycol ether, phenolsulfonic acid-urea-formaldehyde.
Mix intimately with 2 parts by weight of the sodium salt of the condensate and 68 parts by weight of paraffinic mineral oil. A stable oily dispersion is obtained.
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【表】【table】
【表】【table】
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【表】【table】
Claims (1)
に関係なく、水素、１〜４の炭素原子を有するア
ルキル、２〜４の炭素原子を有するアルコキシア
ルキル、３〜５の炭素原子を有するアルコキシカ
ルボニルアルキル、１〜４の炭素原子を有するハ
ロゲンアルキル、場合によつては１〜４の炭素原
子を有するアルキルまたはハロゲンで置換したベ
ンジルであり、R3およびR4は、それぞれ互いに
関係なく、１〜６の炭素原子を有する非置換アル
キルまたはハロゲンでまたは１〜２の炭素原子を
有するアルコキシでまたはハロゲンで置換または
非置換フエニルで置換した１〜４の炭素原子を有
するアルキル、２〜４の炭素原子を有するアルケ
ニル、３〜４の炭素原子を有するアルキニル、場
合によつては１〜４の炭素原子を有するアルキル
で置換した５〜８の炭素原子を有するシクロアル
キル、７〜８の炭素原子を有するビシクロアルキ
ル、10〜15の炭素原子を有するトリシクロアルキ
ル、縮合環系を有するフエニル環、フエニル、一
重または多重に置換されたフエニル、置換基と共
に１〜４の炭素原子を有するアルキル、ハロゲ
ン、または１〜３の炭素原子を有するアルコキシ
であり、かつＸは、水素、１〜４の炭素原子を有
するアルキル、１〜３の炭素原子を有するハロゲ
ンアルキル、１〜２の炭素原子を有するアルコキ
シ、ハロゲン、ニトロ、またはアミノであり、ｎ
は１〜４であり、かつＡ，Ｂ，Ｄ，Ｅは、それぞ
れ互いに関係なく、酸素または硫黄であり、その
際すべての残基Ａ，Ｂ，Ｄ，Ｅが、同時に酸素で
あることはなく、かつその際これら残基の少なく
とも１つは常に硫黄を表わす）で示されることを
特徴とする硫黄含有ジウレタン。 ２ 一般式 （式中Ｚは残基【式】を意味し、Ｙ は残基【式】を意味し、その際Ｚは常 にＹとは異なり、かつR1とR2は、それぞれ互い
に関係なく、水素、１〜４の炭素原子を有するア
ルキル、２〜４の炭素原子を有するアルコキシア
ルキル、３〜５の炭素原子を有するアルコキシカ
ルボニルアルキル、１〜４の炭素原子を有するハ
ロゲンアルキル、場合によつては１〜４の炭素原
子を有するアルキルまたはハロゲンで置換したベ
ンジルであり、R3およびR4は、それぞれ互いに
関係なく、１〜６の炭素原子を有する非置換アル
キルまたはハロゲンでまたは１〜２の炭素原子を
有するアルコキシでまたはハロゲンで置換または
非置換フエニルで置換した１〜４の炭素原子を有
するアルキル、２〜４の炭素原子を有するアルケ
ニル、３〜４の炭素原子を有するアルキニル、場
合によつては１〜４の炭素原子を有するアルキル
で置換した５〜８の炭素原子を有するシクロアル
キル、７〜８の炭素原子を有するビシクロアルキ
ル、10〜15の炭素原子を有するトリシクロアルキ
ル、縮合環系を有するフエニル環、フエニル、一
重または多重に置換されたフエニル、置換基と共
に１〜４の炭素原子を有するアルキル、ハロゲ
ン、または１〜３の炭素原子を有するアルコキシ
であり、かつＸは、水素、１〜４の炭素原子を有
するアルキル、１〜３の炭素原子を有するハロゲ
ンアルキル、１〜２の炭素原子を有するアルコキ
シ、ハロゲン、ニトロ、またはアミノであり、ｎ
は１〜４であり、かつＡ，Ｂ，Ｄ，Ｅは、それぞ
れ互いに関係なく、酸素または硫黄であり、その
際すべての残基Ａ，Ｂ，Ｄ，Ｅが、同時に酸素で
あることはなく、かつその際これら残基の少なく
とも１つは常に硫黄を表わす）で示される硫黄含
有ジウレタンを含有することを特徴とする除草
剤。[Claims] 1. General formula (wherein Z means a residue [formula], Y means a residue [formula], Z is always different from Y, and R 1 and R 2 are each independently hydrogen, Alkyl with 1 to 4 carbon atoms, alkoxyalkyl with 2 to 4 carbon atoms, alkoxycarbonylalkyl with 3 to 5 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, optionally 1 benzyl substituted with alkyl or halogen having ~4 carbon atoms, and R 3 and R 4 are each, independently of each other, unsubstituted alkyl or halogen having 1 to 6 carbon atoms or benzyl substituted with 1 to 2 carbon atoms; alkyl having 1 to 4 carbon atoms substituted with alkoxy having or with halogen or unsubstituted phenyl, alkenyl having 2 to 4 carbon atoms, alkynyl having 3 to 4 carbon atoms, optionally Cycloalkyl with 5 to 8 carbon atoms substituted with alkyl with 1 to 4 carbon atoms, bicycloalkyl with 7 to 8 carbon atoms, tricycloalkyl with 10 to 15 carbon atoms, fused ring systems phenyl ring, phenyl, singly or multiply substituted phenyl, alkyl having 1 to 4 carbon atoms together with substituents, halogen, or alkoxy having 1 to 3 carbon atoms, and X is hydrogen, 1 alkyl having ~4 carbon atoms, halogenalkyl having 1 to 3 carbon atoms, alkoxy having 1 to 2 carbon atoms, halogen, nitro, or amino, n
is 1 to 4, and A, B, D, and E are each independently oxygen or sulfur, in which case all residues A, B, D, and E cannot be oxygen at the same time. , and at least one of these residues always represents sulfur). 2 General formula (wherein Z means a residue [formula], Y means a residue [formula], Z is always different from Y, and R 1 and R 2 are each independently hydrogen, Alkyl with 1 to 4 carbon atoms, alkoxyalkyl with 2 to 4 carbon atoms, alkoxycarbonylalkyl with 3 to 5 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, optionally 1 benzyl substituted with alkyl or halogen having ~4 carbon atoms, and R 3 and R 4 are each, independently of each other, unsubstituted alkyl or halogen having 1 to 6 carbon atoms or benzyl substituted with 1 to 2 carbon atoms; alkyl having 1 to 4 carbon atoms substituted with alkoxy having or with halogen or unsubstituted phenyl, alkenyl having 2 to 4 carbon atoms, alkynyl having 3 to 4 carbon atoms, optionally Cycloalkyl with 5 to 8 carbon atoms substituted with alkyl with 1 to 4 carbon atoms, bicycloalkyl with 7 to 8 carbon atoms, tricycloalkyl with 10 to 15 carbon atoms, fused ring systems phenyl ring, phenyl, singly or multiply substituted phenyl, alkyl having 1 to 4 carbon atoms together with substituents, halogen, or alkoxy having 1 to 3 carbon atoms, and X is hydrogen, 1 alkyl having ~4 carbon atoms, halogenalkyl having 1 to 3 carbon atoms, alkoxy having 1 to 2 carbon atoms, halogen, nitro, or amino, n
is 1 to 4, and A, B, D, and E are each independently oxygen or sulfur, in which case all residues A, B, D, and E cannot be oxygen at the same time. , and at least one of these residues always represents sulfur).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772725146 DE2725146A1 (en) | 1977-06-03 | 1977-06-03 | DIURETHANE AND HERBICIDES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS543038A JPS543038A (en) | 1979-01-11 |
| JPS6151583B2 true JPS6151583B2 (en) | 1986-11-10 |
Family
ID=6010672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6587678A Granted JPS543038A (en) | 1977-06-03 | 1978-06-02 | Sulfurrcontaining diurethanes and herbicide containing same |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0000030B1 (en) |
| JP (1) | JPS543038A (en) |
| AT (1) | AT358869B (en) |
| AU (1) | AU519196B2 (en) |
| BR (1) | BR7803528A (en) |
| CA (1) | CA1110264A (en) |
| CS (1) | CS196429B2 (en) |
| DD (1) | DD135853A5 (en) |
| DE (2) | DE2725146A1 (en) |
| DK (1) | DK247278A (en) |
| ES (1) | ES470367A1 (en) |
| FI (1) | FI781762A (en) |
| HU (1) | HU177551B (en) |
| IE (1) | IE46905B1 (en) |
| IL (1) | IL54779A (en) |
| IT (1) | IT1104710B (en) |
| NO (1) | NO781931L (en) |
| NZ (1) | NZ187460A (en) |
| PL (1) | PL106564B1 (en) |
| PT (1) | PT68091A (en) |
| SU (1) | SU725541A1 (en) |
| TR (1) | TR20048A (en) |
| YU (1) | YU132578A (en) |
| ZA (1) | ZA783163B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3113449A1 (en) * | 1981-04-03 | 1982-11-11 | Hoechst Ag, 6000 Frankfurt | "THIOCARBAMIC ACID ESTER, METHOD FOR THE PRODUCTION THEREOF, MEDICINAL PRODUCTS CONTAINING IT AND THEIR USE" |
| JPS5951205A (en) * | 1982-06-23 | 1984-03-24 | Toyo Soda Mfg Co Ltd | Herbicide containing carbamate derivative |
| DE19800531A1 (en) * | 1998-01-09 | 1999-07-15 | Bayer Ag | Process for the preparation of N- (3-amino-4-fluorophenyl) sulfonamides, N- (3-amino-4-fluorophenyl) carboxamides and N- (3-amino-4-fluorophenyl) - carbamates |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS537474A (en) * | 1976-07-12 | 1978-01-23 | Tsuneto Yoshii | Process for producing soil conditioner and fertilizers from waste woods of artificial bed log for shiitake* shiitake aseptic timber and other edible or medicinal fungi culture base |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1037578B (en) * | 1975-04-23 | 1979-11-20 | Snam Progetti | PROCEDURE FOR THE SYNTHESIS OF ESTERS OF THIOCARBAMIC ACIDS |
-
1977
- 1977-06-03 DE DE19772725146 patent/DE2725146A1/en not_active Withdrawn
-
1978
- 1978-05-24 IL IL54779A patent/IL54779A/en unknown
- 1978-05-26 PT PT197868091A patent/PT68091A/en unknown
- 1978-05-29 AU AU36576/78A patent/AU519196B2/en not_active Expired
- 1978-05-29 IE IE1065/78A patent/IE46905B1/en unknown
- 1978-05-29 CA CA304,279A patent/CA1110264A/en not_active Expired
- 1978-05-30 TR TR20048A patent/TR20048A/en unknown
- 1978-05-31 ES ES470367A patent/ES470367A1/en not_active Expired
- 1978-06-01 DD DD78205730A patent/DD135853A5/en unknown
- 1978-06-01 EP EP78100050A patent/EP0000030B1/en not_active Expired
- 1978-06-01 CS CS783577A patent/CS196429B2/en unknown
- 1978-06-01 PL PL1978207278A patent/PL106564B1/en unknown
- 1978-06-01 SU SU2619253A patent/SU725541A1/en active
- 1978-06-01 BR BR787803528A patent/BR7803528A/en unknown
- 1978-06-01 DE DE7878100050T patent/DE2860287D1/en not_active Expired
- 1978-06-02 YU YU01325/78A patent/YU132578A/en unknown
- 1978-06-02 IT IT49686/78A patent/IT1104710B/en active
- 1978-06-02 NO NO781931A patent/NO781931L/en unknown
- 1978-06-02 ZA ZA00783163A patent/ZA783163B/en unknown
- 1978-06-02 FI FI781762A patent/FI781762A/en not_active Application Discontinuation
- 1978-06-02 AT AT403178A patent/AT358869B/en not_active IP Right Cessation
- 1978-06-02 HU HU78BA3662A patent/HU177551B/en unknown
- 1978-06-02 JP JP6587678A patent/JPS543038A/en active Granted
- 1978-06-02 DK DK247278A patent/DK247278A/en not_active Application Discontinuation
- 1978-06-02 NZ NZ187460A patent/NZ187460A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS537474A (en) * | 1976-07-12 | 1978-01-23 | Tsuneto Yoshii | Process for producing soil conditioner and fertilizers from waste woods of artificial bed log for shiitake* shiitake aseptic timber and other edible or medicinal fungi culture base |
Also Published As
| Publication number | Publication date |
|---|---|
| SU725541A3 (en) | 1980-03-30 |
| EP0000030A1 (en) | 1978-12-20 |
| FI781762A (en) | 1978-12-04 |
| IT1104710B (en) | 1985-10-28 |
| AT358869B (en) | 1980-10-10 |
| PL207278A1 (en) | 1979-03-26 |
| NZ187460A (en) | 1980-11-28 |
| EP0000030B1 (en) | 1980-12-10 |
| BR7803528A (en) | 1979-02-20 |
| ATA403178A (en) | 1980-02-15 |
| IE46905B1 (en) | 1983-11-02 |
| IE781065L (en) | 1978-12-03 |
| HU177551B (en) | 1981-11-28 |
| TR20048A (en) | 1980-07-02 |
| NO781931L (en) | 1978-12-05 |
| ES470367A1 (en) | 1979-09-16 |
| ZA783163B (en) | 1979-07-25 |
| DE2860287D1 (en) | 1981-02-19 |
| YU132578A (en) | 1983-01-21 |
| IL54779A0 (en) | 1978-07-31 |
| DK247278A (en) | 1978-12-04 |
| SU725541A1 (en) | 1980-03-30 |
| JPS543038A (en) | 1979-01-11 |
| DD135853A5 (en) | 1979-06-06 |
| IT7849686A0 (en) | 1978-06-02 |
| IL54779A (en) | 1982-12-31 |
| PT68091A (en) | 1978-05-31 |
| AU519196B2 (en) | 1981-11-19 |
| AU3657678A (en) | 1979-12-06 |
| DE2725146A1 (en) | 1978-12-14 |
| CA1110264A (en) | 1981-10-06 |
| CS196429B2 (en) | 1980-03-31 |
| PL106564B1 (en) | 1979-12-31 |
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