DE2144700C3 - Benzyl-N.N-di-sek.-butylthiolcarbamat, seine Herstellung und Verwendung - Google Patents
Benzyl-N.N-di-sek.-butylthiolcarbamat, seine Herstellung und VerwendungInfo
- Publication number
- DE2144700C3 DE2144700C3 DE2144700A DE2144700A DE2144700C3 DE 2144700 C3 DE2144700 C3 DE 2144700C3 DE 2144700 A DE2144700 A DE 2144700A DE 2144700 A DE2144700 A DE 2144700A DE 2144700 C3 DE2144700 C3 DE 2144700C3
- Authority
- DE
- Germany
- Prior art keywords
- sec
- benzyl
- carbamate
- rice
- plants
- 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
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title claims description 50
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 11
- 241000196324 Embryophyta Species 0.000 claims description 95
- 241000209094 Oryza Species 0.000 claims description 69
- 235000007164 Oryza sativa Nutrition 0.000 claims description 61
- 235000009566 rice Nutrition 0.000 claims description 61
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 230000012010 growth Effects 0.000 claims description 14
- -1 benzyl halide Chemical class 0.000 claims description 9
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 claims description 9
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims description 8
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- QVMFDLLOVZUZLH-UHFFFAOYSA-N n,n-di(butan-2-yl)carbamoyl chloride Chemical compound CCC(C)N(C(Cl)=O)C(C)CC QVMFDLLOVZUZLH-UHFFFAOYSA-N 0.000 claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 239000000370 acceptor Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 78
- 238000011282 treatment Methods 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 238000012360 testing method Methods 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000002689 soil Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000009472 formulation Methods 0.000 description 14
- 239000004009 herbicide Substances 0.000 description 14
- 238000011161 development Methods 0.000 description 12
- 230000018109 developmental process Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 230000002147 killing effect Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 230000004936 stimulating effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000006378 damage Effects 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- UYAQBKOPWJQDRY-UHFFFAOYSA-N C(N)(O)=O.C(CCC)S Chemical compound C(N)(O)=O.C(CCC)S UYAQBKOPWJQDRY-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000003337 fertilizer Substances 0.000 description 6
- 238000009331 sowing Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- UJXIOVIFPTXDHU-UHFFFAOYSA-N 2-phenylethanethioyl chloride Chemical compound ClC(=S)CC1=CC=CC=C1 UJXIOVIFPTXDHU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000009499 grossing Methods 0.000 description 3
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 241000743339 Agrostis Species 0.000 description 2
- 241000748223 Alisma Species 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 230000009418 agronomic effect Effects 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000001066 destructive effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000002367 phosphate rock Substances 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 1
- WIUUBCPPAWFIOL-UHFFFAOYSA-N 4-(6-methylheptoxy)-4-oxo-3-sulfobutanoic acid Chemical compound CC(C)CCCCCOC(=O)C(S(O)(=O)=O)CC(O)=O WIUUBCPPAWFIOL-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000033714 Clidemia hirta Species 0.000 description 1
- 235000014277 Clidemia hirta Nutrition 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000209210 Dactylis Species 0.000 description 1
- 240000004585 Dactylis glomerata Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 244000100545 Lolium multiflorum Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000202758 Scirpus Species 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 240000005498 Setaria italica Species 0.000 description 1
- 235000007226 Setaria italica Nutrition 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 231100000360 alopecia Toxicity 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
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KNLINLAXQBLGJI-UHFFFAOYSA-N bis(2-hydroxyethyl)-(13-phenyltridecyl)azanium;chloride Chemical compound [Cl-].OCC[NH+](CCO)CCCCCCCCCCCCCC1=CC=CC=C1 KNLINLAXQBLGJI-UHFFFAOYSA-N 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
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- CKJFPVNRRHVMKZ-UHFFFAOYSA-L calcium;naphthalene-1-sulfonate Chemical compound [Ca+2].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1.C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 CKJFPVNRRHVMKZ-UHFFFAOYSA-L 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012364 cultivation method Methods 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- CKAOXDUSLQBRSY-UHFFFAOYSA-N dodecyl(2-phenylethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[NH2+]CCC1=CC=CC=C1 CKAOXDUSLQBRSY-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011440 grout Substances 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- UAGGVDVXSRGPRP-UHFFFAOYSA-M n,n-diethylcarbamothioate Chemical compound CCN(CC)C([O-])=S UAGGVDVXSRGPRP-UHFFFAOYSA-M 0.000 description 1
- HXMTZADTMCGSBJ-UHFFFAOYSA-N n-butylcarbamoyl chloride Chemical compound CCCCNC(Cl)=O HXMTZADTMCGSBJ-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000017363 positive regulation of growth Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- BKXRWLMGHBHCFY-UHFFFAOYSA-N s-benzyl n,n-diethylcarbamothioate Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1 BKXRWLMGHBHCFY-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000009333 weeding Methods 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
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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)
- Catching Or Destruction (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2954670 | 1970-09-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2144700A1 DE2144700A1 (de) | 1972-03-16 |
| DE2144700B2 DE2144700B2 (de) | 1979-02-08 |
| DE2144700C3 true DE2144700C3 (de) | 1979-10-04 |
Family
ID=11227655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2144700A Expired DE2144700C3 (de) | 1970-09-10 | 1971-09-07 | Benzyl-N.N-di-sek.-butylthiolcarbamat, seine Herstellung und Verwendung |
Country Status (14)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5458009A (en) * | 1977-10-17 | 1979-05-10 | Toshiba Corp | Magnetic disc device |
| JPS57118584U (enrdf_load_stackoverflow) * | 1981-01-17 | 1982-07-23 | ||
| JPS63164859U (enrdf_load_stackoverflow) * | 1987-04-13 | 1988-10-27 | ||
| JP6405190B2 (ja) | 2014-10-10 | 2018-10-17 | 株式会社コスメック | 出力装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL280296A (enrdf_load_stackoverflow) * | 1961-07-03 |
-
1971
- 1971-09-03 BG BG018497A patent/BG36923A3/xx unknown
- 1971-09-06 SU SU1692768A patent/SU503484A3/ru active
- 1971-09-07 DE DE2144700A patent/DE2144700C3/de not_active Expired
- 1971-09-07 OA OA54356A patent/OA03790A/xx unknown
- 1971-09-07 RO RO7177160A patent/RO64417A/ro unknown
- 1971-09-07 FR FR7132228A patent/FR2107342A5/fr not_active Expired
- 1971-09-07 AU AU33167/71A patent/AU458052B2/en not_active Expired
- 1971-09-07 RO RO7100068159A patent/RO63190A/ro unknown
- 1971-09-07 ES ES394857A patent/ES394857A1/es not_active Expired
- 1971-09-09 GB GB4219771A patent/GB1356306A/en not_active Expired
- 1971-09-09 BR BR5929/71A patent/BR7105929D0/pt unknown
- 1971-09-09 HU HUMO807A patent/HU163427B/hu unknown
- 1971-09-10 PH PH12834A patent/PH10363A/en unknown
- 1971-09-10 JP JP46069787A patent/JPS5231411B1/ja active Pending
-
1973
- 1973-12-31 ES ES421938A patent/ES421938A1/es not_active Expired
- 1973-12-31 ES ES421939A patent/ES421939A1/es not_active Expired
-
1975
- 1975-12-30 MY MY72/75A patent/MY7500072A/xx unknown
-
1976
- 1976-04-09 JP JP51039425A patent/JPS51131851A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SU503484A3 (ru) | 1976-02-15 |
| JPS5231411B1 (enrdf_load_stackoverflow) | 1977-08-15 |
| ES421939A1 (es) | 1976-05-01 |
| AU458052B2 (en) | 1975-02-20 |
| JPS51131851A (en) | 1976-11-16 |
| BR7105929D0 (pt) | 1973-02-15 |
| ES394857A1 (es) | 1974-12-01 |
| PH10363A (en) | 1977-01-18 |
| HU163427B (enrdf_load_stackoverflow) | 1973-08-28 |
| DE2144700A1 (de) | 1972-03-16 |
| ES421938A1 (es) | 1976-05-01 |
| RO63190A (fr) | 1978-08-15 |
| FR2107342A5 (enrdf_load_stackoverflow) | 1972-05-05 |
| AU3316771A (en) | 1973-03-15 |
| DE2144700B2 (de) | 1979-02-08 |
| JPS5344461B2 (enrdf_load_stackoverflow) | 1978-11-29 |
| MY7500072A (en) | 1975-12-31 |
| OA03790A (fr) | 1971-12-24 |
| BG36923A3 (en) | 1985-02-15 |
| RO64417A (ro) | 1980-04-15 |
| GB1356306A (en) | 1974-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |