JPS6222981B2 - - Google Patents
Info
- Publication number
- JPS6222981B2 JPS6222981B2 JP13664880A JP13664880A JPS6222981B2 JP S6222981 B2 JPS6222981 B2 JP S6222981B2 JP 13664880 A JP13664880 A JP 13664880A JP 13664880 A JP13664880 A JP 13664880A JP S6222981 B2 JPS6222981 B2 JP S6222981B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- methoxycarbonyl
- acetylsulfanilamide
- weeds
- germination
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 230000002363 herbicidal effect Effects 0.000 claims description 18
- 239000004009 herbicide Substances 0.000 claims description 16
- -1 N1 -methoxycarbonyl- N4- (4-nitrophenoxy)acetylsulfanilamide Chemical compound 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- IZAJBHQZQNCLOX-UHFFFAOYSA-N methyl N-[4-[[2-(3,5-dichlorophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC(=CC(=C1)Cl)Cl)=O)=O IZAJBHQZQNCLOX-UHFFFAOYSA-N 0.000 claims description 3
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 claims description 3
- UXMAGKILYFLLLD-UHFFFAOYSA-N methyl N-[4-[[2-(2,4-dinitrophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-])=O)=O UXMAGKILYFLLLD-UHFFFAOYSA-N 0.000 claims 2
- WUDZMGQBDQGBMS-UHFFFAOYSA-N methyl N-[4-[[2-(3-nitrophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC(=CC=C1)[N+](=O)[O-])=O)=O WUDZMGQBDQGBMS-UHFFFAOYSA-N 0.000 claims 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 description 62
- 241000196324 Embryophyta Species 0.000 description 42
- 230000000694 effects Effects 0.000 description 33
- 238000011282 treatment Methods 0.000 description 24
- 230000035784 germination Effects 0.000 description 15
- 240000007594 Oryza sativa Species 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000007164 Oryza sativa Nutrition 0.000 description 11
- 235000009566 rice Nutrition 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 231100000674 Phytotoxicity Toxicity 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
- 239000007900 aqueous suspension Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002516 radical scavenger Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 244000301850 Cupressus sempervirens Species 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241001076438 Oxya japonica Species 0.000 description 2
- 244000184734 Pyrus japonica Species 0.000 description 2
- 240000001341 Reynoutria japonica Species 0.000 description 2
- 235000018167 Reynoutria japonica Nutrition 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 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
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 1
- HHQQTVXFKGIICR-UHFFFAOYSA-N 1,2-dichloroethane-1,2-diol Chemical class OC(Cl)C(O)Cl HHQQTVXFKGIICR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OWEDBRWCJFWVFZ-UHFFFAOYSA-N 2-(2,4-dinitrophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O OWEDBRWCJFWVFZ-UHFFFAOYSA-N 0.000 description 1
- LXWGIMHMQOCPCR-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC(Cl)=C1 LXWGIMHMQOCPCR-UHFFFAOYSA-N 0.000 description 1
- NIPZZANLNKBKIS-UHFFFAOYSA-N 2-(3,5-dimethylphenoxy)acetic acid Chemical compound CC1=CC(C)=CC(OCC(O)=O)=C1 NIPZZANLNKBKIS-UHFFFAOYSA-N 0.000 description 1
- ABYSGRXBGLVRGO-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetyl chloride Chemical compound CC1=CC(Cl)=CC=C1OCC(Cl)=O ABYSGRXBGLVRGO-UHFFFAOYSA-N 0.000 description 1
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
- QATKOZUHTGAWMG-UHFFFAOYSA-N 4-fluoro-3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(O)=C1 QATKOZUHTGAWMG-UHFFFAOYSA-N 0.000 description 1
- AVDLFIONKHGQAP-UHFFFAOYSA-N 4-nitrophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1 AVDLFIONKHGQAP-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 229920006070 Nilamid® Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910001502 inorganic halide Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UIUFVYXXKCVRHB-UHFFFAOYSA-N methyl N-[4-[[2-(3,5-dimethylphenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC(=CC(=C1)C)C)=O)=O UIUFVYXXKCVRHB-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YQCUHZQMGUYNJA-UHFFFAOYSA-N sulfanylideneurea Chemical compound NC(=O)N=S YQCUHZQMGUYNJA-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
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The present invention provides N 1 -methoxycarbonyl-N 4 -[2-
(2-Methyl-4-chlorophenoxy)propionyl]sulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dichlorophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dimethylphenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (4-nitrophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (3-nitrophenoxy) Acetyl sulfanilamide, N 1 -methoxycarbonyl-N 4 -
(2,4-dinitrophenoxy)acetylsulfanilamide and N1 -acetyl- N4- (2-methyl-4-chlorophenoxy)acetylsulfur
N4 -phenoxyalkanoylsulfanilamides selected from the group consisting of nilamides (),
The present invention also relates to a herbicide containing at least one of these N4 -phenoxyalkanoylsulfanilamides or water-soluble metal salts thereof as an active ingredient. Compounds of the above formula are, for example, the corresponding phenoxyalkanoyl derivatives ()
When X is a halogen, the reaction is carried out in an inert organic solvent with a salt forming agent or a hydrogen halide scavenger, specifically an inorganic or hydrogen halide scavenger. It proceeds by contacting in the presence of an organic base. Examples of the phenoxyalkanoyl halides in () include 3-nitrophenoxyacetic acid, 4-nitrophenoxyacetic acid, and
-Nitrophenoxyacetic acid, 2,4-dinitrophenoxyacetic acid, 3,5-dichlorophenoxyacetic acid,
3,5-dimethylphenoxyacetic acid, 2-methyl-
Examples include chloride or bromide of 4-chlorophenoxyacetic acid and 2-methyl-4-chlorophenoxypropionic acid. Examples of the sulfanilamide () include N 1 -methoxycarbonylsulfanilamide and N 1 -acetylsulfanilamide. Examples of salt forming agents include sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium amide, sodium alkoxide, and the like; examples of hydrogen chloride scavengers include pyridine and triethylamine. Examples of the inert organic solvent include aromatic hydrocarbons such as benzene and toluene, dioxane, tetrahydrofuran, diethyl ether, pyridine, dimethylformamide, and dimethyl sulfoxide. The use of a solvent that also functions as the hydrogen chloride scavenger, such as pyridine, is convenient for simplifying the manufacturing process. The reaction is usually carried out at room temperature or slightly warmed, but in some cases, the mixture of the sulfanilamide and the solvent in () is cooled, and the acid halide in () is added to it or the solution thereof is added. A method such as dripping may also be used. Thereafter, the reaction is allowed to proceed under desired conditions, and the liquid properties are adjusted to obtain the optimum yield to complete the reaction. In addition, if the physical properties of the starting material and the product are acceptable, for example, if the melting point of the product is sufficiently higher than the melting points of both starting materials and both are highly stable against heat, phenoxyacetic acid, phenoxypropionyl The target substance can also be directly obtained by melting the free carboxylic acid together with the sulfanilamide under reduced pressure without converting the acid into a halide. The compound () obtained by the above method is recrystallized from a suitable solvent, such as aqueous methanol, or purified by chromatography. Alternatively, the obtained compound can be dissolved in water and treated with an alkali metal hydroxide or an alkaline earth metal to form a metal salt thereof. When the compounds () of the present invention are used as herbicides, they are usually diluted with a liquid or solid carrier that is inert to these compounds, and if necessary, a suitable auxiliary agent such as a surfactant is added thereto. emulsion,
It is used in the form of powder, wettable powder, granules, etc. Further, if necessary, other active ingredients may be mixed in for use. Liquid carriers used in the present invention include various organic solvents such as hydrocarbons such as kerosene, benzene, and xylene, halogenated hydrocarbons such as chlorobenzene and dichloroethylene, alcohols, and ketones such as acetone. Solid carriers include bentonite, kaolin, clay, talc, acid clay, diatomaceous earth,
Examples include silica sand, finely powdered silica, and calcium carbonate. Examples of the surfactant include alkylbenzenesulfonates, ligninsulfonates, higher alcohol sulfates, polyoxyethylene sorbitan fatty acid esters, dialkylsulfosuccinates, alkyltrimethylammonium chlorides, and the like. The amount of the compound of the present invention to be used as a herbicide is usually 1.0 to 20.0 g per are as the active ingredient, but it is not necessarily limited to this range, and as described below, the use situation, application method, timing, etc. It can be used in an appropriate amount depending on the crop to which it is applied and other conditions. ããããã
The herbicidal action of the compounds of the present invention is not only more powerful than existing drugs, but also very unique. That is, at least in fields, these act only during the germination of weed seeds and strongly suppress the germination, but they do not act at all on weeds after germination. This is safe for seeds of useful crops that have different germination depths, and it is possible to kill only weeds.Furthermore, by performing treatment after transplanting crops, it is possible to selectively prevent the emergence of only weeds. Can be suppressed. The structure of the compound of the present invention has parts similar to existing known phenoxycarboxylic acid herbicides and N 1 -acylsulfanilamide or sulfanylylurea herbicides, but their herbicidal properties are different from those of these herbicides. It has a completely different taste. This fact was confirmed as a very significant difference in properties by the test examples described below in which these existing herbicides were used as controls. The compounds of the present invention have strong herbicidal activity, and therefore, sufficient effects can be expected with low chemical damage even when applied in small amounts. In this way, this compound can be used not only as a non-selective herbicide for non-agricultural land and forests, but also as a selective herbicide for agricultural land, for soil treatment before or after sowing useful crops, before or after transplantation. For use, its herbicidal activity can be exerted arbitrarily in upland fields or paddy fields. When using the compound of the present invention as a herbicide, the optimum compound should be selected depending on the purpose of use, especially the type of weeds to be removed, and the planting, cultivation, and cropping type of useful crops in the fields or paddy fields to which it will be applied. or combinations are made. The selection or combination of optimal compounds can be carried out as appropriate, taking into consideration the detailed disclosure in the Examples below. Hereinafter, the present invention will be explained in more detail using compound synthesis examples, formulation examples, and test examples. Synthesis Example 1 A mixture of 1-(2-methyl-4-chlorophenoxy)propionic acid (4.0 g, 0.018 mol) and thionyl chloride (4.4 g, 0.037 mol) was mixed at 90-110°C with 3
After refluxing for a while, leave it overnight. Excess thionyl chloride was distilled off under reduced pressure from this reaction solution, and in the solution,
A solution of N 1 -methoxycarbonylsulfanilamide (4.0 g, 0.032 mol) in pyridine (26.0 ml) is added dropwise over about 3 minutes while maintaining the temperature at 15-20°C. The reaction mixture was stirred at 20-30°C for about 1.5 hours, and then a mixture of 35% hydrochloric acid (31.6 g) and water (32 ml) was added to adjust the pH to about 2. As a result, the viscous substance produced in the mixture is separated by decantation, dissolved in a dilute aqueous sodium hydroxide solution, and then about 20% hydrochloric acid is added to remove the precipitated crude crystals. This crude crystal is recrystallized from benzene to give N 1 â
Methoxycarbonyl-N 4 -[2-(2-methyl-
4-Chlorphenoxy)propionyl]sulfanilamide (compound No. 1) is obtained (powder, yield
5.7g, yield 71.6%). Melting point 86-87â. Similarly, Compound No. 3 listed in Table 1 below
I got a score of 7. These N 1 -salts can be easily obtained by reacting these with sodium hydroxide or potassium hydroxide in an aqueous solution. Synthesis Example 2 (2-Methyl-4-chlorophenoxy)acetic acid chloride (10.98 g, 0.048 mol) was added dropwise to a solution of N 1 -acetylsulfanilamide (9.64 g, 0.048 mol) in pyridine (95 ml) to give a solution of 50 to 75 After reacting at â for about 30 minutes with stirring, pyridine was distilled off under reduced pressure. Pour 100ml of water into the residue to make a slurry,
Adjust the pH to 2 with % hydrochloric acid and collect the precipitated crude crystals. Add this crude crystal to acetone (300ml) and water (140ml).
10% sodium hydroxide was added dropwise to dissolve it, and a small amount of decolorizing charcoal was added.The filtered mother liquor was neutralized with 35% hydrochloric acid, the precipitated crystals were removed, and N 1 -acetyl-N 4 -(2-methyl-4-
Chlorphenoxy) acetylsulfanilamide (compound No. 2) was obtained (yield: 11.84 g, yield: 60.24
%, lobular). Melting point 253-255â. ããããã
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ã«ãªã€ãã[Table] Formulation Example 1 Wettable powder: 50 parts of the compound of the present invention, 5 parts of Solpol (Toho Chemical Industries, trade name), 3 parts of Lunox (Toho Chemical Industries, trade name), Carplex #80 (Shionogi Pharmaceuticals, trade name) 15 parts and 27 parts of kaolin are ground and mixed to obtain a wettable powder containing 50% of the active ingredient. 2 Granules: 5 parts of the compound of the present invention, 5 parts of calcium lignosulfonate, 30 parts of bentonite, and 60 parts of clay
After pulverizing, mixing, adding water and kneading to granulate, the mixture is dried to obtain granules containing 5% of the active ingredient. Test Example (Field Condition) Pre-germination and post-germination treatments in Examples 1 to 3 below were carried out in accordance with the following methods. (1) Pre-germination treatment (germination inhibitory activity) test and its evaluation: 25 seeds of test plants were sown according to type into polyethylene cups 9 cm in diameter filled with sandy loam. After seeding, an aqueous suspension of the test compound (compound acetone solution, Tween 20 as a spreading agent, 100 ppm
It was applied to the soil surface using a sprayer and immediately covered with soil to a thickness of about 5 mm. The amount of dilution water was adjusted to 10 per are. Control was carried out in a greenhouse with natural sunlight at a temperature of 25°C, and the results observed 3 weeks after treatment were expressed using the following 6-level evaluation (common to the following tests). 5: Dead or non-germinated 4: On the verge of withering 3: Large effect 2: Small effect 1: Slightly affected 0: No effect (2) Post-emergence treatment (growth inhibition activity) test: 10 days after sowing of test plants The seedlings were treated with the test compound in the same manner as the pre-germination treatment.
Management, observation and evaluation 3 weeks after treatment were performed in the same manner. Example 1 The results are summarized in Table 2. These results demonstrate that the compound of the present invention has the activity of strongly inhibiting weed germination. This has been shown to be in sharp contrast to the post-emergence growth inhibitory activity against the same weed. More specifically, by using the compounds of the present invention before transplanting or during the growing of useful crops, it is possible to control only weeds that will germinate later on without affecting the growth of the crops. Obviouslyããããã
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[Table] Table 2 shows that although the compound of the present invention contains a part of its structure that is similar to that of the control compound, there is a significant difference in herbicidal activity when used. It is shown that there is. For this reason, although there are restrictions on the time when the compounds of the present invention can be treated, as far as farmland is concerned,
It proves to be extremely useful for the treatment of crops after transplantation or post-emergence. Furthermore, whereas the control compound acts after germination or is effective only against broad-leaved weeds, the compound of the present invention has been shown to be effective against both grass and broad-leaved weeds only before germination. . Example 2 In accordance with the post-emergence treatment method described in (2) above, the effects on useful crops after sowing and the germination-suppressing activity of symbiotic weeds were compared, and the results summarized in Table 3 on the next page were obtained. In other words, all of the compounds of the present invention exhibit strong germination-suppressing or herbicidal effects against major weed species occurring in fields through post-sowing treatment, and all have no effect on corn and soybean. Nakatsuta. Of these, compounds Nos. 1, 2, 5 and 6 had no effect on wheat, Nos. 1, 2, 3, 5 and 6 had no effect on cucumber, and No. 5 had no effect on rapeseed. On the other hand, among the control compounds A and B, herbicidal or germination inhibiting activity was observed, but they had a significant effect on all useful crops, and the others (C, D, and E) had no effect on both. It was inactive. ããããã
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[Table] Here, Compound No. 1 had a considerable effect on corn, sorghum, wheat, and beet in the pre-germination treatment, and Compound No. 4 had a considerable effect on wheat, but Compound No. 3 had a considerable effect on wheat. It was confirmed that there was no effect to the extent that it would be a practical problem either before or after germination, and it was confirmed that none of the compounds had any effect on the crops after germination. Linyuron (F), which was used as a control, inhibited the growth of all the tested crops, except for the pre-emergence treatment of maize. Example 4 This example was conducted according to the following test method. (3) Soil mixing treatment test: A vat (40 m x 40 m) was filled with sandy loam soil, a predetermined amount of the test compound was mixed in to a mixing depth of 5 cm, and then the test plants were sown. Management, observation (3 weeks after treatment), and evaluation were performed according to (1) and (2) above, and the results are summarized in Table 5 on the next page. ããããã
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ãçµæãåŸãã[Table] Table 5 shows that even when the compound of the present invention is used in soil mixing treatment to expand the depth of the treatment layer, it has the characteristic that high selectivity between weeds and beneficial effects can be maintained. I can see that you are doing it. Regarding the herbicidal spectrum, Compound No. 1 affected all tested weeds, including Japanese grasshopper, while Compounds No. 3, 4, and 6 had a considerable effect on Japanese grasshopper, Japanese knotweed, and Japanese knotweed.
If the dose is sufficient, it can cause complete or near-killing effects. Regarding the effects on useful crops, none of the compounds showed any phytotoxicity to corn except for Compound No. 1. None of the compounds showed any toxicity to soybean. Compound No. 6 was completely harmless to wheat, and Compounds No. 3, 4, and 6 did not cause any practical damage to tomatoes. From the above results, compound No. 6 is corn,
Compound No. 1 is found in wheat, soybeans, tomatoes, and cucumbers.
Compound No. 3 and 4 were found to be useful for corn and soybeans, and Compound No. 1 was found to be useful for soybeans. Example 5 This example was conducted according to the following test method. (4) Rice test (pot) method: Fill a/5000 Wagner pot with paddy soil,
Pre-flooded weed seeds were sown, and a predetermined amount of an aqueous suspension of the test compound was added dropwise to the weeds before germination. Immediately thereafter, two rice plants per pot were planted. Management was carried out according to (1) to (3) above, and the weight of the plants was measured one month after the treatment and expressed as a percentage (%) of the untreated plant weight, and the results shown in Table 6 below were obtained. .
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ãè¡šããïŒã[Table] As is clear from the previous table, under flooded conditions, all the test compounds suppressed the emergence of major weeds in paddy fields such as Japanese millet, Cyperus japonica, and other broad-leaved weeds at dosages of 5 g/a and 10 g/a. do.
In particular, Compound No. 1 completely inhibits the growth of almost all important weeds in paddy fields at a dosage of 5 g/a. Regarding the safety of the test compounds on rice, a slight effect was observed on Compound No. 1, but no effects were observed on the other compounds. Example 5 (5) Paddy rice test (field) method: Pre-germination treatment A 50 x 50 x 50 cm concrete pot set up in an outdoor field is filled with paddy soil (sandy loam) and 5 cm
The area was flooded. Four rice plants (2.5 leaf stage) per pot were planted there, underground stems or tubers of important perennial weeds in paddy fields were embedded, and annual paddy weeds were sown. Immediately thereafter, a predetermined amount of an aqueous suspension of the test compound was added dropwise for treatment. After being left for 30 days under natural sunlight conditions at an average temperature of 17-28â, rice and annual weeds (naturally occurring)
We pulled out and perennial weeds, separated them, and weighed them to observe and evaluate the weed control effect and impact on rice under paddy field conditions, and obtained the results summarized in Table 7 below in comparison with the untreated plot. (represents grass amount%).
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At each dose, germination of the annual weeds tested was completely suppressed. Furthermore, No. 1 is less effective against perennial weeds that are difficult to control than the control drug H, which is a perennial weed herbicide currently on the market, against Japanese black grubs. It was highly effective. In this case, the effect on rice was significantly lower than that of H. On the other hand, a control drug widely used as an initial herbicide for paddy fields in Japan had no effect on perennial weeds. Comparative drug H, which is a mixture, shows strong phytotoxicity to rice at this treatment stage, whereas Compound No. 1, although a single agent, has only slight phytotoxicity and has excellent properties as a herbicide for paddy fields. It was recognized that Example 6 (6) Rice test (pot) method (growth inhibition effect by post-germination treatment): Pack paddy soil into a/5000 Wagner pot,
Before flooding, seeds of annual weeds were sown and tubers of perennial weeds were planted. Immediately thereafter, two rice plants per pot were planted and flooded. Thereafter, when the rice and weeds reached the following leaf stage (leaf stage), a predetermined amount of the test compound was applied and treated. Rice: 3.8 leaves Cyperus japonica: 3 leaves (15cm) Black-capped cypress: 5 leaves (5cm) Urikawa: 4 leaves (5cm) Japanese millet: 1.5 leaves (8cm) Management was carried out in the same manner as in (4) above, and the effect on rice after 1 month of treatment The effects on weeds were also measured, and the results shown in Table 8 below were obtained.
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[Table] As is clear from the previous table, compound No. 1 is
At a dosage of 10 g/a, it completely suppressed annual broad-leaved weeds and showed a moderate suppressive effect on perennial weeds such as pine snail and cypress. In contrast, control drugs A' and E' had little effect on both annual and perennial weeds. In this way, under flooded conditions, Compound No. 1 is effective against broad-leaved weeds and perennial weeds with considerably advanced leaf stages.
It was also found that it is effective against herbicides and has excellent properties as a paddy herbicide. ããããã
Claims (1)
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æããé€èå€ã[Claims] 1 N 1 -methoxycarbonyl-N 4 -[2-(2-
Methyl-4-chlorophenoxy)propionyl]
Sulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dichlorophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dimethylphenoxy)acetyl Sulfanilamide, N1 -methoxycarbonyl- N4- (4-nitrophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4-
(3-nitrophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (2.4
-dinitrophenoxy)acetylsulfanilamide and N1 -acetyl- N4- (2-methyl-4
-N4 -phenoxyalkanoylsulfanilamide selected from the group consisting of -chlorophenoxy)acetylsulfanilamide. 2 N 1 -Methoxycarbonyl-N 4 -[2-(2-
Methyl-4-chlorophenoxy)propionyl]
Sulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dichlorophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dimethylphenoxy)acetyl Sulfanilamide, N1 -methoxycarbonyl- N4- (4-nitrophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4-
(3-nitrophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (2.4
-dinitrophenoxy)acetylsulfanilamide and N1 -acetyl- N4- (2-methyl-4
A herbicide containing as an active ingredient at least one N 4 -phenoxyalkanoylsulfanilamide or a water-soluble metal salt thereof selected from the group consisting of -chlorophenoxy)acetylsulfanilamide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13664880A JPS5759855A (en) | 1980-09-29 | 1980-09-29 | N4-phenoxyalkanoylsulfanilamide and herbicide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13664880A JPS5759855A (en) | 1980-09-29 | 1980-09-29 | N4-phenoxyalkanoylsulfanilamide and herbicide |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5759855A JPS5759855A (en) | 1982-04-10 |
JPS6222981B2 true JPS6222981B2 (en) | 1987-05-20 |
Family
ID=15180231
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP13664880A Granted JPS5759855A (en) | 1980-09-29 | 1980-09-29 | N4-phenoxyalkanoylsulfanilamide and herbicide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5759855A (en) |
-
1980
- 1980-09-29 JP JP13664880A patent/JPS5759855A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5759855A (en) | 1982-04-10 |
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