NO744703L - - Google Patents
Info
- Publication number
- NO744703L NO744703L NO744703A NO744703A NO744703L NO 744703 L NO744703 L NO 744703L NO 744703 A NO744703 A NO 744703A NO 744703 A NO744703 A NO 744703A NO 744703 L NO744703 L NO 744703L
- Authority
- NO
- Norway
- Prior art keywords
- substituted
- salts
- acids
- amides
- esters
- Prior art date
Links
- -1 haloalkyl radicals Chemical group 0.000 claims description 28
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 19
- 150000001408 amides Chemical class 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 13
- 239000013543 active substance Substances 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- SHXGGYLLZCCNAX-UHFFFAOYSA-N (3-chlorophenyl) carbamate Chemical compound NC(=O)OC1=CC=CC(Cl)=C1 SHXGGYLLZCCNAX-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates 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
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- MFVFDTCSVFBOTL-UHFFFAOYSA-N 1,3-diazetidine Chemical class C1NCN1 MFVFDTCSVFBOTL-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- JCRNSBKSAQHNIN-UHFFFAOYSA-N 2,4-dibutylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC(CCCC)=C21 JCRNSBKSAQHNIN-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- QTDIEDOANJISNP-UHFFFAOYSA-N 2-dodecoxyethyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOCCOS(O)(=O)=O QTDIEDOANJISNP-UHFFFAOYSA-N 0.000 description 1
- UOCUSOBVEHOMMB-UHFFFAOYSA-N 2h-1$l^{6},2,3-benzothiadiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)NN=CC2=C1 UOCUSOBVEHOMMB-UHFFFAOYSA-N 0.000 description 1
- BXVXHZXQVJERJR-UHFFFAOYSA-N 4-chlorobut-3-yn-2-yl n-(3-chlorophenyl)carbamate Chemical compound ClC#CC(C)OC(=O)NC1=CC=CC(Cl)=C1 BXVXHZXQVJERJR-UHFFFAOYSA-N 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- JHIKYTSPSBOJLJ-UHFFFAOYSA-N 4-hydroxybut-3-yn-2-yl carbamate Chemical compound NC(=O)OC(C)C#CO JHIKYTSPSBOJLJ-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical group C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 241000551547 Dione <red algae> Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000002303 anti-venom Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical class O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- QQSGDKKFXBGYON-UHFFFAOYSA-N ethoxy-methylperoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane Chemical class CCOP(=S)(OOC)OC1=CC(C)=NC(C(C)C)=N1 QQSGDKKFXBGYON-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 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 1
- 238000000227 grinding Methods 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UJJUEJRWNWVHCM-UHFFFAOYSA-N n-methylsulfamoyl chloride Chemical compound CNS(Cl)(=O)=O UJJUEJRWNWVHCM-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- SDRLFDJOSQLRPB-UHFFFAOYSA-N oxadiazine-4,5-dione Chemical class O=C1CON=NC1=O SDRLFDJOSQLRPB-UHFFFAOYSA-N 0.000 description 1
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003585 thioureas Chemical group 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Den foreliggende oppfinnelse angår nye substituerte butynylkarbamater med herbicid virkning, samt herbicider inneholdende disse forbindelser, og deres anvendelse som herbicider.
Bruken av 4~klorbutyn-2-yl-N-(3-klorfenyl)-karbamat som herbicid er kjent (DT-AS 1 137 255). Dets virkning er imidlertid liten.
Det ble nå funnet at butynylkarbamater med formelen Is
hvor R1 betyr en arylrest som på enkelt eller blandet måte eventuelt er substituert med ett eller flere halogenatomer, nitrogrup-2 per, alkylgrupper, alkoksygrupper, halogenalkylrester, R betyr hydrogen eller en alkylrest (metyl, etyl, propyl, isopropyl, bu-tyl, isobutyl, sek.butyl) eller en halogenalkylrest (B-kloretyl), • har en god herbicid virkning. De nye substituerte butynylkarbamater med formelen I kan fremstilles ved omsetning av et 4-hydroksybutyn-2-yl-karbamat med den generelle formel II hvor R<1>har samme betydning som ovenfor, med et aminosulfonylhalo-genid med den generelle formal III hvor R 2 har samme betydning som ovenfor, og hvor x er halogen (for eksempel klor eller brom). Denne fremstillingsmåte er foretrukket. Likeledes kan de nye butynylkarbamater med den generelle formel I fremstilles ved omsetning av en forbindelse med den generelle formel IV
hvor R 2 har samme betydning som ovenfor, med et isocyanat med den
generelle formel V hvor R<1>har samme betydning som ovenfor, eller med et fosgen og et amin med den generelle formel VI
hvor R1 har den ovenfor angitte betydning.
Forbindelsene med de generelle formler,II, III og IV er generelt kjent eller kan fremstilles som følger: Forbindelser med den generelle formål II kan fremstilles ved omsetning av en 1,4-butyndiol og et isocyanat med formelen V, eller fosgen og et amin med formelen VI. Forbindelser med formelen III kan blant annet fremstilles etter de fremgangsmåter som er beskre-vet i Liebigs Ann. Chem. 729 40 - 51 (1969). Forbindelser med formelen IV kan fremstilles ved omsetning av en 1,4-butyndiol og en forbindelse med formelen III R NHSOjX, hyor x er halogen.
De følgende eksempler vil ytterligere belyse oppfinnelsen.
Eksempel 1
Til en oppløsning av 23,95 vektdeler 4-hydroksy-butyn-2-yl-N-(3-klorf enyl)-karbamat i 650vektdeler metylenklorid ble det ved 0-5°c og under omrøring samtidig tilsatt 20,8 vektdeler metyl-aminosulfonylklorid (ca. 90%'s) og 16,6 vektdeler trletylamin. 30 minutter etter at reaksjonen var fullført ble reaksjonsblandlngen behandlet med isvann, fortynnet vandig saltsyre, vann, natriumbi-karbonatoppløsning og til slutt igjen med vann. Etter inndamping av den med magnesiumsulfat tørrede metyienkloridoppløsning fikk man 33 deler råprodukt, sm.p. 99-102°C.
Etter omkrystallisering fra 1,2-dikloretan/benzen smelter forbindelsen ved 103-105°c.
Forbindelsen 4-metylaminosulfonyloksy-butyn-l-yl-N-(3-klor-fenyl)-karbamat har følgende formelt
De følgende forbindelser med den generelle formel I ble fremstilt analogt den i eksempel 1 beskrevne metode, idet man gikk ut fra det tilsvarende 4-hydroksy-butyn-2-yl-substituerte karbamat og et tilsvarende aminosulfonylklorid.
De virksomme stoffer har en sterk herbicid virkning og kan derfor anvendes som ugrasdrepende midler eller til bekjempelse av uønsket plantevekst. Om midlene anvendes som totale eller selektive midler avhenger hovedsakelig av den mengde virksomt stoff som anvendes pr. flateenhet.
Mad ugras eller uønsket plantevekst menes alle enfrøbladede og tofrøbladede planter som vokser på steder hvor de Ikke er øns-ket.
Således kan eksempelvis de følgende planter bekjempes med midlene ifølge oppfinnelseni
Planter av grasfamillen, så som
Herbicidene ifølge oppfinnelsen Han anvendes i kornkul-turer, så som og i kulturer av tofrøblådédé planter, så som
De mengder som anvendes av midlene ifølge oppfinnelsen, kan variere. Mengden avhenger hovedsakelig av arten av den Ønskede
virkning.
Den mengde som anvendes, ligger i regelen mellom 0,1 og
15 kg eller mer, fortrinnsvis mélloø 0,2 og 6 kg, virksomt stoff pr. hektar. v
Midlene ifølge oppfinnelsen kan blant annet anvendes før plantingen, etter plantingen, før såingen, før plantene kommer opp av jorden, etter at plantene er kommet opp av jorden eller mens kultur- eller de uønskede planter er i ferd med å komme opp av jorden, og midlene kan brukes en eller flere ganger.
Anvendelsen skjer eksempelvis i form av direkte sprøytbare løsninger, pulvere, suspensjoner eller dispersjoner, emulsjoner, oljedispersjoner, pastaer, støvformige midler, strømidler, granulater, ved sprøyting, forstøving, utspreding eller utheIling. An-vende lees formene retter seg helt etter anvendelsesformålets man tar alltid sikte på å oppnå en mest mulig fin fordeling av de virksomme stoffer ifølge oppfinnelsen.
For fremstilling av direkte sprøytbare løsninger, emulsjoner, pastaer og oljedispersjoner kan man bruke mineraloljefraksjoner med midlere til høyt kokepunkt, så som kerosin eller dieselolje, ennvidere kulltjsereoljer etc., samt oljer av vegetabilsk eller ani-malsk opprinnelse, alifatiske, cykliske og aromatiske hydrokarboner, som for eksempel benzen, toluen, xylen, paraffin, tetrahydronafta-lin, alkylerte naftaliner eller deres derivater, for eksempel meta-nol, etanol, propanol, butanol, kloroform, karbontetraklorid, cyk-loheksanol, cykloheksanon, klorbenxen, isoforon etc., sterkt po-lare løsningsmidler som for eksempel dimetylformamid, dimetylsulfok-syd, N-metylpyrrolidon, vann etc.
Vandige bruksformer kan fremstilles av emulsjonskonsentrater, pastaer eller fuktbare pulvere,(sprøytepulvere) eller oljedispersjoner ved tilsetning av vann. ved fremstilling av emulsjoner, pastaer eller oljedispersjoner kan stoffene som sådanne eller løst i olje eller løsningsmiddel homogeniseres i vann ved hjelp av fukte-, klebe-, dispergerings- eller emulgeringsmidler. Det kan imidlertid også fremstilles konsentrater bestående av virksomt stoff, fukte-, klebe-, dispergerings- eller emulgeringsmiddel og eventuelt løsnings-middel eller olje, hvilke konsentrater er egnet til å fortynnes med vann.
Blant overflateaktive stoffer kan neveess alkali-, jord-alkali-, ammoniumsalter av ligninsulfonsyre, naftalinsulfonsyrér, fenolsulfonsyrer, alkylarylsulfonater, alkylsulfater, alkylsulfo-nater. alkali- og jordalkaUsalter ay dibutylnaftalinsulfonsyre, lauryletersulfat, fettelkoholsulfater, f ettsure alkali- og jord-
alkalisalter; salter av sulfaterte heksadekanoler, heptadekanoler, oktadekanoler, salter av sulfatert féttalkoholglykoleter, kondensasjonsprodukter av sulfonert naftalin og naftalinderivater med formaldehyd, kondensasjonsprodukter av naftalin eller naftalinsul-fonsyrer med fenol og formaldehyd, polyoksyotylén-oktylfenoleter, etoksylert isooktylfenol-, oktylfenol-, nonylfenol, alkylfenol-polyglykoleter, tributylfenylpolyglykoleter, alkylarylpolyeter-alkoholer, isotridecylalkohol, fettalkoholetylenoksyd-kondensater, etoksylert ricinusolje.polyoksyetylenalkyleter, etoksylert poly-oksypropylen, laurylalkoholpolyglykoleteracetal, sorbitolester,
lignin, sulfittavluter og metylcellulose.
Pulver, stjfø- og støvformigé midler kan fremstilles ved blanding eller sammaling av de virksomme stoffer med et fast bære-materiale.
Granulater, for eksempel omhyllings-, impregnerings- og homogengranulater kan fremstilles ved binding av de virksomme stoffer på faste bærematerialer. Faste bærematerialer er eksempelvis mineraImaterialer så som silikagel, kiselsyrer, kiselgeler, silika-ter, talkum, kaolin, attaclay, kalkstein, kalk, kritt, bolus, løss,
leire, dolomitt, diatoméjord, kalsium- og magnesiumsulfat, raagne-siumoksyd, malte harpikser, gjødningsstoffer som for eksempel am-moniumsulfat, ammoniumfosfat, amraonlumnitrat, urinstoff er og vege-tabilske produkter så som mel av korn, bark, tre dg nøtteskall, cellulosepulver og andre faste bærematerialer.
Preparatene inneholder mellom 0,1 og 95 vekt% virksomt
stoff, fortrinnsvis mellom 0,5 og 90 vekt%.v
Til blandingene eller de enkelte virksomme stoffer kan man, eventuelt først umiddelbart før anvendelsen (tankblanding), tilsette oljer av forskjellige typer, herbicider, fungicider, nematocider,
insekticider, baktericider, sporelementer, gjødningsstoffer, skum-hindrende midler (for eksempel silikoner), vekstrogulotorer, iaot-giftmidler eller andre herbicid virksomme forbindelser, som for :■ eksempel
substituerte aniliner
substituerte aryloksykarboksyloyrer og deres salter, estere og amider,
substituerte etere
substituerte arsonsyrer og deres salter, estere og amider substituerte benziroidazoler
substituerte benzisotiazoler
substituerte isooksazolpyrimidoner
substituerte imidaeoler
substituerte isotiazolpyrimidoner
substituerte ketoner
substituerte naftokinoner
substituerte alifatiske nitriler
substituerte aromatiske nitriler
substituerte oksadiaeoler
substituerte oksadiazinoner
substituerte oksadiazolidindioner
substituerte oksadiazindioner
substituerte fenoler og deres salter og estere substituerte fosforsyrer og deres salter, estere og amider substituerte fosfoniumklorider
substituerte fosfonalkylglyciner
substituerte fosfiter
substituerte fosforsyrer og deres salter, estere og amider substituerte piperidiner
substituerte pyrazoler
substituerte pyrazolalkylkarboksylsyrer og deres salter, estere og amider
substituerte pyrazoliumsalter
substituerte pyrazoliumalkylsulfater
substituerte pyridaziner , substituerte pyridazoner
substituerte pyridinkarboksylsyrer og deres salter,0 estere og amider
substituerte benztiadiazinondioksyder
substituerte benzoksaziner
substituerte benzoksazinoner substituerte benztiadiazoler
substituerte blureter
substituerte kinoliner
substituerte karbamater
substituerte alifatiske karboksylsyrer og deres salter, estere og amider
substituerte aromatiske karboksylsyrer og deres salter/ estere
pg, amider substituerte karbamoylalkyl-tiol- oller ditiofosfater substituerte kinaisoliner
substituerte cykloslkylamidekarbontiolsyrer og deres salter, ©ster© og amider substituerte cykloalRylkarbonaiaido-tiaEolQr
substituerte dikarboksylsyrer og salter, ester© og amider substituert© dihydrobensofurany1sulf onater
substituert© disulfider
substituert© dipyridyltumsoltsr
substituerte ditlokarbamator
oubstituert©ditiofosforsyrer og derec salter,©-ster©og amider substituort© urinotoffer
substituert©heksabydrb-l-H-knrbotioater substituerte hydantc-åner substituerte hydrasider
substituert© hydrasoniumsalter
substituert©pyridiner substituerte pyridinkarboksyleter 1 ■ substituert© pyridinoner eebstituert©pyrimidiner s substituert© pyrimldoner
substituert© pyrrolidinkarboksylsyr©og dennes saltor, ©ster© og-amider substituert©pyrrolidiner
substituerte pyrrolidoner ..substituert©/arylsulfonsyrer og dores, salter/ester©og amider - ' substirusrt©: • styraner ..'''Substituerte totrahydro-oksédioBindioner substituort© tetrahydro-oksadiaEoldioner, substituerte tetrahydrometanbindoner substituert©tetrahydro-dioEOl-tioner substituert©tøtrahydro-tiadiaBin-tioner substituert©tetrahydro-tiadiasoldioner
substituert© aromatiske tiokarbokoylsyreamider
substituert© tiokarboksylsyrer og deres salter, estere og amider substituert®; tiolkarbamater ' substituert© tiourinstoff©r substituerte tiofosforsyrer og deres salter, ester© og amider.
substituerte triaziner
sugstituerte triazoler
substituerte uraciler
substituerte uretidindioner.
De sistnevnte herbicide forbindelser kan bringes til anvendelse før eller etter de virksomme enkeltstoffer eller blandinger ifølge oppfinnelsen.
Tilblandingen av disse midler til herbicidene ifølge oppfinnelsen kan skje i vektforholdet 1:10 til 10:1. Det samme gjelder for oljer, fungicider/ nematocider, insekticider, baktericider, mot-giftmidler og vekstregulatorer.
Eksempel 2
I et drivhus ble forskjellige planter ved en veksfchøyde på 2-18 cm behandlet med de virksomme stoffer
4-metylaminosulfonyloksy-butyn-2-yl-N-(3-klorfenyl)-karbamat (I)
4-etylarainosulfonyloksy-butyn-2-yl-N~(3-klorfenyl)-karbamat (II)
og det virksomme sammenligningsstoff
4-klor-butyn-2-yl-N-(3-klorfenyl)-karbamat (III).
De anvendtejmengder var i hvert tilfelle 0,5 kg virksomt stoff pr. hektar og var i hvert tilfelle dispergert eller emulgert i 500 liter vann pr. hektar.
Etter 2-3 uker ble det slått fast at de virksomme stoffer
I og II viste en bedre herbicid virkning ved samme forenlighet med kulturplantene enn det virksomme stoff III.
Forsøksresultatet vil fremgå av den følgende tabell.
Eksempel 3
I et drivhus ble leirholdig sandjord fy lit i forsøkakasser, og frø av forskjellige planter ble sådd. Umiddelbart deretter fulgte behandling med
4-metylarainosulfonyloksy-butyn-2-yl-N-(3-klorfenyl)-karbamat (I)
4-«tylaminosulfony,lokay-butyn-2-yl-N-(3-klorfenyl)-karbamat (II)
og til sammenligning med
4-klor-butyn-2-yl-N-(klorfenyl)-karbamat (III),
i hvert tilfelle med en anvendt mengde på 2 kg virksomt stoff pr. hektar, dispergert eller emulgert i 500 liter vann pr. hektar.
Etter 3-4 uker ble det slått fast at de virksomme stoffer I og II viste en bedre herbicid virkning ved samme forenlighet med kulturplantene enn sammenligningsmiddelet III.
Resultatet vil fremgå av den følgende tabell.
Claims (1)
- Herbicid,karakterisert vedat det inneholder et butynylkarbamat med formelen1 hvor R betyr en arylrest som eventuelt er enhetlig eller blandet substituert med et eller flere halogenatomer, nitrogrupper, alkylgrupper, alkoksygrupper, halogenalkylrester, og hvor R 2 betyr hydrogen eller en alkylrest eller en halogenalkylrest.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2364876A DE2364876A1 (de) | 1973-12-28 | 1973-12-28 | Butinylcarbamate |
Publications (1)
Publication Number | Publication Date |
---|---|
NO744703L true NO744703L (no) | 1975-07-28 |
Family
ID=5902098
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO744703A NO744703L (no) | 1973-12-28 | 1974-12-27 |
Country Status (22)
Country | Link |
---|---|
JP (1) | JPS5095427A (no) |
AR (1) | AR207026A1 (no) |
AT (1) | AT338557B (no) |
AU (1) | AU7659974A (no) |
BE (1) | BE823160A (no) |
BG (1) | BG21835A3 (no) |
BR (1) | BR7410809D0 (no) |
CS (1) | CS192465B2 (no) |
DD (1) | DD115562A5 (no) |
DE (1) | DE2364876A1 (no) |
DK (1) | DK682674A (no) |
EG (1) | EG11491A (no) |
ES (1) | ES433385A1 (no) |
FR (1) | FR2272077A1 (no) |
GB (1) | GB1488274A (no) |
IL (1) | IL46284A (no) |
IT (1) | IT1050276B (no) |
LU (1) | LU71281A1 (no) |
NL (1) | NL7416702A (no) |
NO (1) | NO744703L (no) |
PL (1) | PL92121B1 (no) |
SE (1) | SE7415553L (no) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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KR970027051A (ko) * | 1995-11-02 | 1997-06-24 | 조규향 | 카바모일기를 포함하는 신규한 설파메이트 화합물 |
-
1973
- 1973-12-28 DE DE2364876A patent/DE2364876A1/de active Pending
-
1974
- 1974-01-01 AR AR257104A patent/AR207026A1/es active
- 1974-11-13 LU LU71281A patent/LU71281A1/xx unknown
- 1974-11-18 JP JP49132104A patent/JPS5095427A/ja active Pending
- 1974-12-10 BE BE151336A patent/BE823160A/xx unknown
- 1974-12-11 SE SE7415553A patent/SE7415553L/xx unknown
- 1974-12-11 FR FR7440792A patent/FR2272077A1/fr not_active Withdrawn
- 1974-12-18 AU AU76599/74A patent/AU7659974A/en not_active Expired
- 1974-12-18 IL IL46284A patent/IL46284A/en unknown
- 1974-12-18 IT IT54633/74A patent/IT1050276B/it active
- 1974-12-20 NL NL7416702A patent/NL7416702A/xx unknown
- 1974-12-20 DD DD183285A patent/DD115562A5/xx unknown
- 1974-12-20 GB GB55094/74A patent/GB1488274A/en not_active Expired
- 1974-12-23 CS CS748972A patent/CS192465B2/cs unknown
- 1974-12-24 BG BG28545A patent/BG21835A3/xx unknown
- 1974-12-26 BR BR10809/74A patent/BR7410809D0/pt unknown
- 1974-12-27 DK DK682674A patent/DK682674A/da unknown
- 1974-12-27 NO NO744703A patent/NO744703L/no unknown
- 1974-12-27 ES ES433385A patent/ES433385A1/es not_active Expired
- 1974-12-27 AT AT1033674A patent/AT338557B/de not_active IP Right Cessation
- 1974-12-27 PL PL1974176899A patent/PL92121B1/xx unknown
- 1974-12-28 EG EG587/74A patent/EG11491A/xx active
Also Published As
Publication number | Publication date |
---|---|
NL7416702A (nl) | 1975-07-01 |
GB1488274A (en) | 1977-10-12 |
AR207026A1 (es) | 1976-09-09 |
AU7659974A (en) | 1976-06-24 |
DK682674A (no) | 1975-09-08 |
ATA1033674A (de) | 1976-12-15 |
IL46284A (en) | 1977-11-30 |
AT338557B (de) | 1977-09-12 |
PL92121B1 (no) | 1977-03-31 |
JPS5095427A (no) | 1975-07-29 |
CS192465B2 (en) | 1979-08-31 |
BG21835A3 (no) | 1976-09-20 |
BR7410809D0 (pt) | 1975-09-02 |
IL46284A0 (en) | 1975-03-13 |
SE7415553L (no) | 1975-06-30 |
BE823160A (fr) | 1975-06-10 |
ES433385A1 (es) | 1976-12-01 |
EG11491A (en) | 1977-09-30 |
IT1050276B (it) | 1981-03-10 |
LU71281A1 (no) | 1975-05-28 |
DD115562A5 (no) | 1975-10-12 |
DE2364876A1 (de) | 1975-07-03 |
FR2272077A1 (no) | 1975-12-19 |
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