JPH0471041B2 - - Google Patents
Info
- Publication number
- JPH0471041B2 JPH0471041B2 JP59267466A JP26746684A JPH0471041B2 JP H0471041 B2 JPH0471041 B2 JP H0471041B2 JP 59267466 A JP59267466 A JP 59267466A JP 26746684 A JP26746684 A JP 26746684A JP H0471041 B2 JPH0471041 B2 JP H0471041B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- groups
- general formula
- substituted
- represented
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 41
- 230000002363 herbicidal effect Effects 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 239000004009 herbicide Substances 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 claims description 3
- -1 N-substituted chloroacetanilide Chemical class 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000009472 formulation Methods 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- 239000008187 granular material Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- 230000000379 polymerizing effect Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 8
- 235000012239 silicon dioxide Nutrition 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 239000012433 hydrogen halide Substances 0.000 description 7
- 229910000039 hydrogen halide Inorganic materials 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000000454 talc Substances 0.000 description 6
- 229910052623 talc Inorganic materials 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 150000001448 anilines Chemical class 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 235000013312 flour Nutrition 0.000 description 5
- 239000002516 radical scavenger Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000009333 weeding Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000238366 Cephalopoda Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003945 anionic surfactant Substances 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
- 238000009835 boiling Methods 0.000 description 3
- 239000000378 calcium silicate Substances 0.000 description 3
- 229910052918 calcium silicate Inorganic materials 0.000 description 3
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 235000019832 sodium triphosphate Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- XXXFZKQPYACQLD-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl acetate Chemical compound CC(=O)OCCOCCO XXXFZKQPYACQLD-UHFFFAOYSA-N 0.000 description 2
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions 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
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N (2,6-Me2C6H3)NH2 Natural products CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CUOSYYRDANYHTL-UHFFFAOYSA-N 1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid;sodium Chemical compound [Na].CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC CUOSYYRDANYHTL-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- VURUNMWLBDYAMB-UHFFFAOYSA-N 2-butylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CCCC)=CC=C21 VURUNMWLBDYAMB-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 239000004859 Copal Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000301850 Cupressus sempervirens Species 0.000 description 1
- 229920002871 Dammar gum Polymers 0.000 description 1
- 239000004860 Dammar gum Substances 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001536352 Fraxinus americana Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000782205 Guibourtia conjugata Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241001076438 Oxya japonica Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- DSRXQXXHDIAVJT-UHFFFAOYSA-N acetonitrile;n,n-dimethylformamide Chemical compound CC#N.CN(C)C=O DSRXQXXHDIAVJT-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 210000003323 beak Anatomy 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000004071 biological effect Effects 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
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical class NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical group O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- JTXUVYOABGUBMX-UHFFFAOYSA-N didodecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCC JTXUVYOABGUBMX-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 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
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000010436 fluorite Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000010985 glycerol esters of wood rosin Nutrition 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 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
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([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
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical group [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004712 n-pentylthio group Chemical group C(CCCC)S* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- LCRMGUFGEDUSOG-UHFFFAOYSA-N naphthalen-1-ylsulfonyloxymethyl naphthalene-1-sulfonate;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(OCOS(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 LCRMGUFGEDUSOG-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000642 polymer Chemical class 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- IXYACKYHUWCLAM-UHFFFAOYSA-M sodium;2-ethylhex-1-ene-1-sulfonate Chemical compound [Na+].CCCCC(CC)=CS([O-])(=O)=O IXYACKYHUWCLAM-UHFFFAOYSA-M 0.000 description 1
- FGDMJJQHQDFUCP-UHFFFAOYSA-M sodium;2-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C(C)C)=CC=C21 FGDMJJQHQDFUCP-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
〔産業上の利用分野〕
本発明はＮ−置換クロロアセトアニリドにホワ
イトカーボン（以下ホワイカと略記する）類を混
合することを特徴とする除草剤組成物に関するも
のである。
〔従来の技術及び発明が解決しようとする問題
点〕
本質的に除草剤製剤に要求される性質として、
下記の４つの事項がある。即ち、１つには先物に
安全であること、２つには雑草に対してムラのな
い安定した除草効果を示すこと。３つには除草剤
の効力が長期的に持続すること、４つには環境問
題、コスト等から有効成分が低含有量でより効果
的な除草作用を有すること、である。
本発明者らは優れた除草剤として下記の一般式
で示される製剤の開発を目指して鋭意研究を重ね
た。
下記の一般式〔〕、
（但し、式中R1、R2及びR3は同種又は異種の水
素原子、ハロゲン原子、アルキル基、アルコキシ
基、アルキルチオ基、アルコキシアルキル基又は
アルキルチオアルキル基を示し、R4は水素原子
又はアルキル基を示し、R5、R6及びR7は同種又
は異種の水素原子、ハロゲン原子、アルキル基、
アルケニル基、アルキニル基、アルコキシ基、又
はアルキルチオ基を示す。）
で表わされるＮ−置換−クロロアセトアニリドを
既に提案した（特願昭58−111077号その他）。当
然のことではあるが、除草剤の効果発現に於ける
製剤の役割は非常に重要なものである。即ち、原
体のもつ物理的あるいは化学的性質を熟慮して最
適の製剤処方を行わない限り十分な除草効果を期
待することはほとんど不可能である。
本発明者らは、上記一般式〔〕で示されるＮ
−置換−クロロアセトアニリドを除草剤として、
より効果的に使用することを目的として、その製
剤処方に関して鋭意研究を続けてきたところ、上
記一般式〔〕で示されるＮ−置換−クロロアセ
トアニリドにホワイカ類を混合することによつて
得られる除草剤組成物が、それぞれ単独の性質か
らは全く予期できない程の相乗作用を現わすこ
と、即ち、低薬量で安定した除草効果をもつこと
を見い出した。本発明者らはこれらの新知見に基
づき、本発明を完成し提案するに至つた。
〔問題点を解決するための手段〕
本発明は、下記一般式〔〕、
（但し、式中R1、R2及びR3は同種又は異種の水
素原子、ハロゲン原子、アルキル基、アルコキシ
基、アルキルチオ基、アルコキシアルキル基又は
アルキルチオアルキル基を示し、R4は水素原子
又はアルキル基を示し、R5、R6及びR7は同種又
は異種の水素原子、ハロゲン原子、アルキル基、
アルケニル基、アルキニル基、アルコキシ基、又
はアルキルチオ基を示す。）
で表わされるＮ−置換−クロロアセトアニリドと
ホワイカ類を混合することを特徴とする除草剤組
成物である。
尚本発明で云うホワイカ類とは人工的に造られ
た微粒子のケイ酸、ケイ酸塩を包含するシリカ系
白色充填剤の総称である。
本発明の除草剤組成物の成分は、下記の一般式
〔〕で示されるＮ−置換−クロロアセトアニリ
ドである。
上記一般式〔〕で示されるＮ−置換−クロロ
アセトアニリドのうち、チオフエン環の２位と
[Industrial Application Field] The present invention relates to a herbicidal composition characterized by mixing N-substituted chloroacetanilide with white carbon (hereinafter abbreviated as white carbon). [Problems to be solved by the prior art and the invention] Properties essentially required for herbicide preparations include:
There are four matters below. That is, one, it must be safe for future use, and two, it must exhibit an even and stable weeding effect against weeds. The third reason is that the herbicide's effectiveness lasts for a long period of time, and the fourth reason is that the herbicide has a more effective herbicidal effect with a lower content of active ingredients due to environmental issues, cost, etc. The present inventors have conducted extensive research with the aim of developing a formulation represented by the following general formula as an excellent herbicide. The following general formula [], (However, in the formula, R 1 , R 2 and R 3 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups or alkylthioalkyl groups, and R 4 represents a hydrogen atom or an alkyl group, R 5 , R 6 and R 7 are the same or different hydrogen atoms, halogen atoms, alkyl groups,
Indicates an alkenyl group, an alkynyl group, an alkoxy group, or an alkylthio group. ) have already been proposed (Japanese Patent Application No. 111077/1983 and others). Naturally, the role of formulations in the expression of herbicide effects is very important. In other words, it is almost impossible to expect a sufficient herbicidal effect unless the physical or chemical properties of the drug substance are carefully considered and the optimal formulation is formulated. The present inventors have discovered that N represented by the above general formula []
-Substituted-chloroacetanilide as a herbicide,
With the aim of using it more effectively, we have continued intensive research on its formulation, and have found that weed killers obtained by mixing whicas with the N-substituted chloroacetanilide represented by the above general formula [] It has been discovered that the drug composition exhibits a synergistic effect that could not be predicted from the properties of each agent alone, that is, it has a stable herbicidal effect at a low dose. Based on these new findings, the present inventors have completed and proposed the present invention. [Means for solving the problems] The present invention is based on the following general formula [], (However, in the formula, R 1 , R 2 and R 3 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups or alkylthioalkyl groups, and R 4 represents a hydrogen atom or an alkyl group, R 5 , R 6 and R 7 are the same or different hydrogen atoms, halogen atoms, alkyl groups,
Indicates an alkenyl group, an alkynyl group, an alkoxy group, or an alkylthio group. This is a herbicidal composition characterized by mixing N-substituted-chloroacetanilide represented by the following formula with a whiker. In the present invention, the term "white ash" is a general term for silica-based white fillers containing artificially produced fine particles of silicic acid and silicate. The component of the herbicidal composition of the present invention is an N-substituted-chloroacetanilide represented by the following general formula []. Among the N-substituted-chloroacetanilides represented by the above general formula [], the 2-position of the thiophene ring
【式】とが結合しており、R1が水素原子また
はアルキル基、R2、R3及びR4が水素原子であり、
R5はアルキル基であり、R6が水素原子、アルキ
ル基またはアルコキシ基であり、R7は水素原子、
アルキル基またはハロゲン原子である化合物は、
米国特許第3901917号により公知である。しかし、
その他の大部分は、新規な化合物である。
前記一般式〔〕中、R1、R2、R3、R5、R6及
びR7で示されるハロゲン原子の具体例としては、
塩素、臭素、フツ素、ヨウ素の各原子が挙げられ
る。また、前記一般式中、R1、R2、R3、R4、
R5、R6及びR7で示されるアルキル基は、直鎖状、
分枝状のいずれであつても良く、炭素数も特に制
限されない。しかし、原料入手の容易さから炭素
数は１〜６個であることが好適である。該アルキ
ル基の具体例を例示すると、メチル基、エチル
基、ｎ−プロピル基、iso−プロピル基、ｎ−ブ
チル基、iso−ブチル基、ｔ−ブチル基、ｎ−ペ
ンチル基、ｎ−ヘキシル基等が挙げられる。前記
一般式〔〕中、R1、R2、R3、R5、R6及びR7で
示されるアルコキシ基は特に限定されないが、一
般には炭素原子数１〜６個の直鎖状または分枝状
の飽和あるいは不飽和基が好適である。一般に好
適に使用される該アルコキシ基の具体例を提示す
ると、メトキシ基、エトキシ基、ｎ−プロポキシ
基、ｔ−ブトキシ基、ｎ−ペントキシ基、ｎ−ヘ
キソキシ基、アリルオキシ等が挙げられる。
前記一般式〔〕中、R1、R2、R3、R5、R6及
びR7で示されるアルキルチオ基は、特に限定さ
れず公知のものが使用出来るが、一般には炭素原
子数１〜６個の直鎖状または分枝状の飽和あるい
は不飽和基が好適である。好適に使用される該ア
ルキルチオ基の具体例を提示すると、メチルチオ
基、エチルチオ基、ｎ−プロピルチオ基、ｔ−ブ
チルチオ基、ｎ−ペンチルチオ基、ｎ−ヘキシル
チオ基、アリルチオ基等が挙げられる。また、前
記一般式中、R1、R2、及びR3で示されるアルコ
キシアルキル基は炭素数に特に制限されないが、
炭素数２〜６個の直鎖状または分枝状の飽和ある
いは不飽和基が好適であり、該アルコキシアルキ
ル基の具体例を例示すると、メトキシメチル基、
メトキシエチル基、エトキシメチル基、ｎ−プロ
ポキシメチル基、ｔ−ブトキシエチル基、アリル
オキシエチル基等が挙げられる。更にまた、前記
一般式中、R1、R2、及びR3で示されるアルキル
チオアルキル基は炭素数に特に制限されないが、
炭素数２〜６個の直鎖状または分枝状の飽和ある
いは不飽和基が好適であり、該アルキルチオアル
キル基の具体例を例示すると、メチルチオメチル
基、メチルチオエチル基、エチルチオメチル基、
ｎ−プロピルチオメチル基、ｔ−ブチルチオエチ
ル基、アリルチオエチル基等が挙げられる。ま
た、前記一般式中、R5、R6、及びR7で示される
アルケニル基は、直鎖状、分枝状を問わず、炭素
数も特に制限されない。しかし、原料入手の容易
さから炭素数は２〜４個であることが好適であ
る。該アルケニル基の具体例を例示すると、ビニ
ル基、アリル基、iso−プロペニル基、２−ブテ
ニル基、３−ブテニル基等が挙げられる。また、
前記一般式中、R5、R6及びR7で示されるアルキ
ルニル基は、直鎖状、分枝状を問わず、炭素数も
特に制限されないが、前記と同様に炭素数が２〜
４個であることが好適である。該アルキニル基の
具体例を例示すると、エチニル基、２−プロピル
ニル基が挙げられる。
上記のＮ−置換−クロロアセトアニリドのう
ち、R1が同種又は異種のハロゲン原子、アルコ
キシ基、アルキルチオ基、アルコキシアルキル
基、又はアルキルチオ基、アルコキシアルキル
基、又はアルキルチオアルキル基であり、R2及
びR3が同種又は異種の水素原子、ハロゲン原子、
アルキル基、アルコキシ基、アルキルチオ基、ア
ルコキシアルキル基、又はアルキルチオアルキル
基であり、R4は水素原子又はアルキル基であり、
R5、R6及びR7は同種又は異種の水素原子、ハロ
ゲン原子、アルキル基、アルケニル基、アルキニ
ル基、アルコキシ基又はアルキルチオ基である化
合物は、15ｇ／10aあるいはそれ以下の低濃度で
使用しても、ノビエなどの一年生雑草及びミズガ
ヤツリなどの多年生雑草をも完全に枯死させる程
の優れた除草効果をもつばかりでなく、500ｇ／
10aという高濃度で使用しても稲に対して全く無
害であるため、本発明に於いて好適に用いられ
る。就中、R1〜R3のうち少なくとも１つが水素
原子以外の置換基であり、この置換基がチオフエ
ン環に結合した[Formula] is bonded, R 1 is a hydrogen atom or an alkyl group, R 2 , R 3 and R 4 are hydrogen atoms,
R 5 is an alkyl group, R 6 is a hydrogen atom, an alkyl group, or an alkoxy group, R 7 is a hydrogen atom,
A compound that is an alkyl group or a halogen atom is
It is known from US Pat. No. 3,901,917. but,
Most of the others are new compounds. In the general formula [], specific examples of the halogen atoms represented by R 1 , R 2 , R 3 , R 5 , R 6 and R 7 include:
Examples include chlorine, bromine, fluorine, and iodine atoms. Furthermore, in the general formula, R 1 , R 2 , R 3 , R 4 ,
The alkyl groups represented by R 5 , R 6 and R 7 are linear,
It may be in any branched form, and the number of carbon atoms is not particularly limited. However, from the viewpoint of easy availability of raw materials, the number of carbon atoms is preferably 1 to 6. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, t-butyl group, n-pentyl group, n-hexyl group. etc. In the general formula [], the alkoxy groups represented by R 1 , R 2 , R 3 , R 5 , R 6 and R 7 are not particularly limited, but are generally linear or branched groups having 1 to 6 carbon atoms. Branched saturated or unsaturated groups are preferred. Specific examples of the alkoxy group that are generally preferably used include methoxy group, ethoxy group, n-propoxy group, t-butoxy group, n-pentoxy group, n-hexoxy group, allyloxy group, and the like. In the general formula [], the alkylthio groups represented by R 1 , R 2 , R 3 , R 5 , R 6 and R 7 are not particularly limited and any known alkylthio group can be used, but they generally have 1 to 1 carbon atoms. Six straight-chain or branched saturated or unsaturated groups are preferred. Specific examples of the alkylthio group suitably used include methylthio group, ethylthio group, n-propylthio group, t-butylthio group, n-pentylthio group, n-hexylthio group, and allylthio group. Furthermore, in the general formula, the alkoxyalkyl groups represented by R 1 , R 2 , and R 3 are not particularly limited in number of carbon atoms, but
Straight chain or branched saturated or unsaturated groups having 2 to 6 carbon atoms are preferred, and specific examples of the alkoxyalkyl group include methoxymethyl group,
Examples include methoxyethyl group, ethoxymethyl group, n-propoxymethyl group, t-butoxyethyl group, and allyloxyethyl group. Furthermore, in the general formula, the alkylthioalkyl groups represented by R 1 , R 2 , and R 3 are not particularly limited in number of carbon atoms,
Straight chain or branched saturated or unsaturated groups having 2 to 6 carbon atoms are preferred, and specific examples of the alkylthioalkyl group include methylthiomethyl group, methylthioethyl group, ethylthiomethyl group,
Examples include n-propylthiomethyl group, t-butylthioethyl group, and allylthioethyl group. Furthermore, in the general formula, the alkenyl groups represented by R 5 , R 6 , and R 7 may be linear or branched, and the number of carbon atoms is not particularly limited. However, from the viewpoint of easy availability of raw materials, the number of carbon atoms is preferably 2 to 4. Specific examples of the alkenyl group include vinyl group, allyl group, iso-propenyl group, 2-butenyl group, and 3-butenyl group. Also,
In the above general formula, the alkylnyl group represented by R 5 , R 6 and R 7 may be linear or branched, and the number of carbon atoms is not particularly limited.
It is preferable that the number is four. Specific examples of the alkynyl group include an ethynyl group and a 2-propylnyl group. In the above N-substituted-chloroacetanilide, R 1 is the same or different halogen atom, alkoxy group, alkylthio group, alkoxyalkyl group, or an alkylthio group, alkoxyalkyl group, or alkylthioalkyl group, and R 2 and R 3 is the same or different hydrogen atom, halogen atom,
an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, or an alkylthioalkyl group, R 4 is a hydrogen atom or an alkyl group,
Compounds in which R 5 , R 6 , and R 7 are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, or alkylthio groups may be used at a low concentration of 15 g/10a or less. However, it not only has an excellent weeding effect that completely kills annual weeds such as field weeds and perennial weeds such as water cypress, but also has an excellent weeding effect of 500 g/
Since it is completely harmless to rice even when used at a high concentration of 10a, it is suitably used in the present invention. In particular, at least one of R 1 to R 3 is a substituent other than a hydrogen atom, and this substituent is bonded to the thiophene ring.
【式】のオルソ位に置換して
おり、R4は水素原子であり、さらにR5〜R7のう
ち少くとも２つが水素原子以外の置換基であり、
これらの置換基がフエニル基の２位と６位に置換
したＮ−置換−クロロアセトアニリドが上記の性
質がより強いため、特に好ましく用いられる。
前記一般式〔〕で示されるＮ−置換−クロロ
アセトアニリドの構造は、次の手段によつて確認
することができる。
(イ) 赤外吸収スペクトル（IR）を測定すること
により、3150−2800cm-1付近にCH結合に基づ
く吸収、1680−1660cm-1付近にアミド基のカル
ボニル結合に基づく特性吸収を観察することが
出来る。
(ロ) 質量スペクトル（MS）を測定し、観察され
る各ピーク（一般にはイオン質量数ｍをイオン
の荷電数ｅで除したｍ／ｅで表わされる値）に
相当する組成式を算出することにより、測定に
供した化合物の分子量ならびに該分子内におけ
る各原子団の結合様式を知ることが出来る。す
なわち、測定に供した試料を一般式〔〕
で表わした場合、一般に分子イオンピーク（以
下Ｍ
と略記する）が分子中に含有されるハロ
ゲン原子の個数に応じて同位体存在比に従つた
強度比で観察されるため、測定に供した化合物
の分子量を決定することが出来る。さらに前記
一般式〔〕で示されるＮ−置換−クロロアセ
トアニリドについては、Ｍ
−Cl、Ｍ
−
COCH2Cl及び
に相当する特徴的な強いピークが観察され、該
分子の結合様式を知ることが出来る。
(ハ) 1H−核磁気共鳴スペクトル（1H−NMR）
を測定することにより、前記一般式〔〕で表
わされるＮ−置換−クロロアセトアニリド中に
存在する水素原子の結合様式を知ることが出来
る。前記一般式〔〕で示されるＮ−置換−ク
ロロアセトアニリドの1H−NMR（δ、ppm：
テトラメチルシラン基準、重クロロホルム溶媒
中）の具体例として、Ｎ−〔2′−（5′−ブロム）
−チエニルメチル〕−Ｎ−クロロアセト−２，
６−ジメチルアニリドについて1H−NMR図を
第１図に示す。その解析結果を示すと次のとお
りである。
すなわち、2.0ppmにプロトン６個分に相当
する一重線が認められ、これはフエニル基の２
及び６位に置換したメチル基(d)によるものと帰
属できる。3.6ppmにプロトン２個分の相当す
る一重線が認められ、これはクロルアセチル基
中のメチレン基(h)によるものと帰属できる。
4.75ppmにプロトン２個分に相当する一重線が
認められ、これはメチレン基(c)によるものと帰
属できる。6.67ppmにプロトン２個分に相当す
る四重線が認められ、これはチオフエン環に置
換したプロトン(a)、(b)によるものと帰属でき
る。6.95〜7.30ppmにプロトン３個分に相当す
る多重線が認められ、これはフエニル基に置換
したプロトン(e)、(h)、(g)によるものと帰属でき
る。
前述の一般式〔〕で示されるＮ−置換−ク
ロロアセトアニリドの1H−NMRの特徴を総括
すると、クロロアセチル基のメチレンプロトン
は、通常一重線で3.6〜3.8ppm付近に現われ、
R4が水素原子である場合にはアミノメチレン
基のメチレンプロトンは一重線で4.7〜5.0ppm
付近に（ただし、アニリン側の２、６位が非対
称的に置換基が存在する場合には二重線となつ
て現われる場合がある）、R4がアルキル基であ
る場合にはアミノメチン基のメチンプロトンは
5.7〜6.7ppmに、チオフエン環側のプロトンは
5.8〜7.4ppmに、ベンゼン環側のプロトンは6.0
〜7.7ppmに特徴的なピークを示す傾向がある。
(ニ) 元素分析によつて炭素、水素、窒素、硫黄、
及びハロゲンの各重量％を求め、さらに確認さ
れた各元素の重量％の和を100から減じること
により、酸素の重量％を算出することが出来、
従つて、組成式を決定することが出来る。
また、Ｎ−置換−クロロアセトアニリドは、
前記一般式〔〕中のR1、R2、R3、R4、R5、
R6及びR7の種類によつてその性状が多少異な
るが、一般に常温常圧においては淡黄色または
黄色の粘稠液体または固体であり、極めて高沸
点を有するものが多い。具体的には後述する合
成例に示すが、上記化合物は一般の有機化合物
と同じように分子量が大きくなる程沸点が高く
なる傾向がある。該化合物は、ベンゼン、エー
テル、アルコール、クロロホルム、四塩化炭
素、アセトニトリル、Ｎ，Ｎ−ジメチルホルム
アミド、ジメチルスルホキシドなどの一般有機
溶媒に可溶であるが、水にはほとんど溶けな
い。
前記一般式〔〕で示されるＮ−置換−クロロ
アセトアニリドの製造方法は特に限定化されるも
のではない。代表的な製造方法を記述すれば以下
のとおりである。一般式〔〕、
（但し、式中R1、R2及びR3は同種又は異種の水
素原子、ハロゲン原子、アルキル基、アルコキシ
基、アルキルチオ基、アルコキシアルキル基又は
アルキルチオアルキル基を示し、R4は水素原子
又はアルキル基を示し、R5、R6及びR7は同種又
は異種の水素原子、ハロゲン原子、アルキル基、
アルケニル基、アルキニル基、アルコキシ基、又
はアルキルチオ基を示す。）
で表わされるアニリン誘導体と、一般式
ClCH2COX（ただし、Ｘはハロゲン原子を示す。）
で表わされるクロロアセチルハロゲニドとを反応
させることによつて、前記一般式〔〕で表わさ
れるＮ−置換−クロロアセトアニリドを得ること
が出来る。
原料となる前記一般式〔〕で表わされるアニ
リン誘導体は如何なる方法で得られたものでも使
用出来る。
前記一般式〔〕で表わされる化合物とクロロ
アセチルハロゲニドとの反応において、両化合物
の仕込みモル比は必要に応じて適宜決定すればよ
いが、通常等モルもしくはクロロアセチルハロゲ
ニドをやや過剰モルを使用するのが一般的であ
る。
また前記反応においてはハロゲン化水素が副生
する。このハロゲン化水素は反応系内で一般式
〔〕で表わされるアニリン誘導体と反応し、生
成物の収率を低下させる原因になるので、通常は
反応系内にハロゲン化水素捕捉剤を共存させるこ
とが好ましい。該ハロゲン化水素捕捉剤は特に限
定されず公知のものを使用することが出来る。一
般に好適に使用される該捕捉剤としてトリメチル
アミン、トリエチルアミン、トリプロピルアミン
等のトリアルキルアミン、ピリジン、ナトリウム
アルラート、炭酸ナトリウム等が挙げられる。
前記反応に際しては一般に有機溶媒を用いるの
が好ましい。該溶媒として好適に使用されるもの
を例示すれば、ベンゼン、トルエン、キシレン、
ヘキサン、ヘプタン、石油エーテル、クロロホル
ム、塩化メチレン、塩化エチレン等の脂肪族また
は芳香族の炭化水素類あるいはハロゲン化炭化水
素類；ジエチルエーテル、ジオキサン、テトラヒ
ドロフラン等のエーテル類；アセトン、メチルエ
チルケトン等のケトン類；アセトニトリルなどの
ニトリル類；Ｎ，Ｎ−ジメチルホルムアミド、
Ｎ，Ｎ−ジエチルホルムアミド等のＮ，Ｎ−ジア
ルキルアミド類；ジメチルスルホキシド等が挙げ
られる。
前記反応における原料の添加順序は特に限定さ
れないが、一般には溶媒に前記一般式〔〕で示
されるアニリン誘導体を溶解して反応器に仕込み
溶媒に溶解したクロロアセチルハロゲニドを撹拌
下に添加するのがよい。勿論連続的に反応系に原
料を添加し生成した反応物を連続的に該反応系か
ら取出すことも出来る。
前記反応における温度は広い範囲から選択出
来、一般には−20℃〜150℃好ましくは０℃〜120
℃の範囲から選べば十分である。反応時間は原料
の種類によつてもちがうが、通常５分〜10日間、
好ましくは１〜40時間の範囲から選べば十分であ
る。また反応中においては、撹拌を行うのが好ま
しい。
反応系から目的生成物すなわち前記一般式
〔〕で示されるＮ−置換−クロロアセトアニリ
ドを単離精製する方法は特に限定されず公知の方
法を採用出来る。例えば反応液を冷却または自然
放冷で、室温またはその近くにもどし、反応溶
媒、残存するハロゲン化水素捕捉剤を留去した
後、残渣をベンゼン抽出する。上記操作で、副生
するハロゲン化水素とハロゲン化水素捕捉剤とか
ら生成する塩及び高分子量化合物を分離する。該
ベンゼン層については、芒硝、塩化カルシウム等
の乾燥剤で乾燥した後、ベンゼンを留去し、残渣
を真空蒸留することによつて目的物を取得する。
真空蒸留により単離精製する他、クロマトグラフ
イーによる精製、あるいは生成物が固体である場
合にはヘキサン等の溶媒から再結晶することによ
り精製することも出来る。
前記一般市〔〕で示されるＮ−置換−クロロ
アセトアニリドの他の製造方法として、次に述べ
る方法も好ましく採用される。
一般式
（但し、式中R1、R2及びR3は同種又は異種の水
素原子、ハロゲン原子、アルキル基、アルコキシ
基、アルキルチオ基、アルコキシアルキル基、ア
ルキルチオアルキル基を示し、R4は水素原子又
はアルキル基を示し、Ｘはハロゲン原子を示す。）
で表わされる置換−チオフエンと、一般式
（但し、式中、R5、R6及びR7は同種又は異種の
水素原子、ハロゲン原子、アルキル基、アルケニ
ル基、アルキニル基、アルコキシ基、アルキルチ
オ基を示す。）
で表わされるクロロアセトアニリドとを反応させ
ることによつても前記一般式〔〕で表わされる
Ｎ−置換−クロロアセトアニリドを得ることが出
来る。
原料となる該置換チオフエンならびに該クロロ
アセトアニリドは如何なる方法で得られたもので
も使用出来る。また、該反応を実施する際の諸条
件ならびに単離精製方法は既に述べた一般式
〔〕で示されるアニリン誘導体とクロロアセモ
ルハロゲニドとの反応において用いた諸条件がな
らびに単離精製方法とほぼ同様な条件が採用出来
る。
前記の一般式〔〕で示されるＮ−置換−クロ
ロアセトアニリドは水田に発生するノビエ、コナ
ギ、等の一年生雑草に加え、ホタルイ、オモダカ
等の多年生雑草に対して幅広い殺草スペクトラム
を有し、かつ水稲に薬害を与えることなく、効率
的に防除し得る優れた除草剤である。
本発明の除草剤組成物の他方の成分はホワイカ
類である。該ホワイカ類は特に限定されず公知の
ものがそのまま使用される。例えば化学工業社発
行「プラスチツクおよびゴム用添加剤実用便覧」
（昭和45年８月10日発行）541頁〜560頁に示され
るような人工的に製造されたケイ酸、ケイ酸塩が
好適に使用出来る。特に湿式法で製造された含水
ケイ酸、乾式法で製造された無水ケイ酸と称され
るホワイカが好適である。またケイ酸塩のなかで
は微粉のケイ酸カルシウムが好適である。これら
のホワイカ類は単独で使用してもまた異種のもの
を混合して使用してもよい。
上述の如く本発明の除草剤組成物は、前記一般
式〔〕で示されるＮ−置換クロロアセトアニリ
ドと、ホワイカ類とを含有する混合物からなり、
本発明のＮ−置換クロロアセトアニリドとホワイ
カ類との除草剤組成物に於いて、Ｎ−置換クロロ
アセトアニリドとホワイカ類は極めて幅広い使用
割合で優れた除草効果が得られる。しかし、一般
的にホワイカ類の使用量は前記Ｎ−置換−クロロ
アセトアニリドに対して重量で15〜400倍の範囲
好ましくは30〜200倍の範囲となるように選べば
好適である。
本発明の除草剤組成物は粒剤としての使用で効
果を発揮するものがあるが、該粒剤の製法は特に
限定されず公知の方法をそのまま採用出来る。例
えば前記Ｎ−置換−クロロアセトアニリド及びホ
ワイカ類以外に、通常、粒剤の調製に使用され
る、界面活性剤、担体、崩壊性等の性状を改善す
る目的で使用される補助剤（一般にカゼイン、ゼ
ラチン、ニカワ、セルローズ等の高分子化合物）
等の混合は本発明の効果をそこなわない限り適宜
選択して使用出来る。
例えば次ぎのような方法が好適に採用出来る。
即ち、Ｎ−置換−クロロアセトアニリド１重量
部、界面活性剤及び水をよく混練し、続いて、ホ
ワイカ類を含んだ担体及び界面活性剤を加えて、
よくかきまぜた後、所定の粒径に押し出し、乾燥
することにより粒剤を得る方法がある。
該担体は公知なものから適宜選べばよいが一般
に好適に使用されるものを例示すれば、例えばカ
オリナイト群、モンモリロナイト群、アタパルジ
ヤイト群或いはジークライト等で代表されるクレ
ー類；タルク、雲母、葉ロウ石、軽石、バーミキ
ユライト、石こう、炭酸カルシウム、ドロマイ
ト、けいそう土マグネシウム、石灰、リン灰石、
ゼライト；大豆粉、タバコ粉、クルミ粉、小麦
粉、木粉、結晶セルロース等の植物性有機物質；
クマロン樹脂、石油樹脂、アルキド樹脂、ポリ塩
化ビニル、ポリアルキレングリコール、ケトン樹
脂、エステルガム、コーパルガム、ダンマルガム
等の合成または天然の高分子化合物；カルナバロ
ウ、蜜ロウ等のワツクス類あるいは尿素の固体担
体等が挙げられる。
また、液体担体としては、ケロシン、鉱油、ス
ピンドル油、ホワイトオイル等のパラフイン径も
しくはナフテン系炭化水素；ベンゼン、トルエ
ン、キシレン、エチルベンゼン、クメン、メチル
ナフタリン等の芳香族炭化水素；四塩化炭素、ク
ロロホルム、トリクロルエチレン、モノクロルベ
ンゼン、ｏ−クロルトルエン等の塩素系炭化水
素；ジオキサン、テトラヒドロフランのようなエ
ーテル類；アセトン、メチルエチルケトン、ジイ
ソブチルケトン、シクロヘキサノン、アセトフエ
ノン、イソホロン等のケトン類；酢酸エチル、酢
酸アミル、エチレングリコールアセテート、ジエ
チレングリコールアセテート、ジエチレングリコ
ールアセテート、マレイン酸ジブチル、コハク酸
ジエチル等のエステル類；メタノール、ｎ−ヘキ
サノール、エチレングリコール、ジエチレングリ
コール等のアルコール類；エチレングリコールフ
エニルエーテル、ジエチレングリコールエチルエ
ーテル、ジエチレングリコールブチルエーテル等
のエーテルアルコール類；ジメチルホルムアミ
ド、ジメチルスルホキシド等の極性溶媒あるいは
水等が挙げられる。
また前記界面活性剤としては、非イオン性、陽
イオン性、陰イオン性及び両イオン性のものが使
用されるが通常は非イオン性および（または）陰
イオン性のものが好適に使用される。適当な非イ
オン性界面活性剤としては、たとえば、ラウリル
アルコール、ステアリルアルコール、オレイルア
ルコール等の高級アルコールにエチレンオキシド
を重合付加させたもの；イソオクチルフエノー
ル、ノニルフエノール等のアルキルフエノールに
エチレンオキシドを重合付加させたもの；イソオ
クチルフエノール、ノニルフエノール等のアルキ
ルフエノールにエチレンオキシドを重合付加させ
たもの；ブチルナフトール、オクチルナフトール
等のアルキルナフトールにエチレンオキシドを重
合付加させたもの；パルミチン酸、ステアリン
酸、オイレン酸等の高級脂肪酸にエチレンオキシ
ドを重合付加させたもの；ステアリルりん酸、ジ
ラウリルりん酸もモノもしくはジアルキルりん酸
にエチレンオキシドを重合付加させたもの；ドデ
シルアミン、ステアリン酸アミド等のアミンにエ
チレンオキシドを重合付加させたもの；ソルビタ
ン等の多価アルコールの高級脂肪酸エステルおよ
びそれにエチレンオキシドを重合付加させたも
の；エチレンオキシドとプロピレンオキシドを重
合付加させたもの；ジオクチルサクシネート等の
多価脂肪酸とアルコールとのエステル等があげら
れる。適当な陰イオン性界面活性剤としては、た
とえば、ラウリル硫酸ナトリウム、オレイルアル
コール硫酸エステルアミン塩等のアルキル硫酸エ
ステル塩；スルホこはく酸ジオクチルエステルナ
トリウム、２−エチルヘキセンスルホン酸ナトリ
ウム等のアルキルスルホン酸塩；イソプロピルナ
フタレンスルホン酸ナトリウム、メチレンビスナ
フタレンスルホン酸ナトリウム、リグニンスルホ
ン酸ナトリウム、ドデシルベンゼンスルホン酸ナ
トリウム等のアリールスルホン酸塩；トリポリり
ん酸ソーダ等のりん酸塩等が挙げられる。
（作用及び効果）
本発明の除草剤組成物はその組成内にホワイカ
類を含有しないものに比べて、或いはホワイカの
含有量が少ないものに比べて著しく安定した薬効
を発現し、更にはＮ−置換−クロロアセトアニリ
ドの含有量を減らしても同等或いはそれ以上の除
草効果を発現するようになる。しかしながらこれ
らの効果の発現作用がどのような作用機構で発現
するのか現在尚明確ではない。たゞホワイカ類を
混合した粒剤は水中での崩壊拡展性が該ホワイカ
類を含まない粒剤に比べると異質である現象を考
慮すると、この崩壊拡展性の相違が生物効果に何
らかの影響を与えていると推定される。
本発明の除草剤組成物は、剤草の発芽前および
発芽後に処理しても効果を有し、土壌処理、茎葉
処理においても高い効果が得られる。施用場所と
しては水田はもちろんのこと、各種穀類、マメ
類、ワタ、そ菜類等の畑、果樹園、芝生地、牧草
地、茶園、桑園、森林地、非農耕地等で広範囲に
有用である。
また本発明の除草剤組成物は除草剤に要求され
る性質を十分に満すものであつて、その有用性は
極めて大きい。
（実施例）
以下に、本発明の除草剤組成物を実施例で具体
例で説明するが、本発明は、これら実施例に限定
されるものではない。
Ｎ−置換−クロロアセトアニリドの合成
合成例 １
Ｎ−〔2′−（5′−ブロム）−チエニルメチル〕−
２，６−ジメチルアニリン1.81ｇ（6.14×
10-3mole）をベンゼン40mlに溶解しトリエチル
アミン0.81ｇ（7.98×10-3mole）を加え、氷水中
に設置した。次いでクロルアセチルクロリド0.83
ｇ（7.37×10-3mole）のベンゼン溶液（15ml）を
徐々に添加した。３時間撹拌した後、50℃で１時
間加熱した。該反応混合物を室温に冷却した後、
水50ml、2N−塩酸50ml、続いて水50mlによつて
順次洗浄し、ベンゼン層を無水硫酸ナトリウムで
乾燥した。その後カラムクロマトにて精製し、黄
色固体1.13ｇを得た。このものの赤外吸収スペク
トルを測定した結果、3110〜2900cm-1にＣ−Ｈ結
合に基づく吸収、1670cm-1にアミド基のカルボニ
ル結合に基づく強い吸収を示した。その元素分析
値はC48.43％、H4.05％、N3.99％であつて、
C15H15NSOBrCl（372.71）に対する計算値である
C48.20％、H4.32％、N3.75％に良く一致した。
また、質量スペクトルを測定したところ、ｍ／
e371に分子量に対応する分子イオンピーク（Ｍ
）、ｍ／e336にＭ
−Clに対応するビーク、
ｍ／e293にＭ
−COCH2Clに対応するピーク、
ｍ／e143（100％）に
に対応する各ピークを示した。
さらに、1H−核磁気共鳴スペクトルについて
は、明細書に具体例として示したとおりである。
上記の結果から、単離生成物がＮ−〔2′−（5′−
ブロム）−チエニルメチル〕−Ｎ−クロロアセト−
２，６−ジメチルアニリド（以下、化合物(1)と略
記する）であることが明らかとなつた。収率はＮ
−〔2′−（5′−ブロム）−チエニルメチル〕−２，６
−ジメチルアニリンに対し、49.5％（3.04％×
10-3mole）であつた。
合成例 ２
合成例１と同様にして合成したＮ−置換−クロ
ロアセトアニリドの性状、物性（沸点）、赤外ス
ペクトルにおける特性吸収値及び元素分析結果を
併せて第１表に略記した。
尚、第１表中の一般式
は、前記一般式〔〕
に対応し、Ａは[Formula] is substituted at the ortho position, R 4 is a hydrogen atom, and at least two of R 5 to R 7 are substituents other than hydrogen atoms,
N-substituted chloroacetanilide in which these substituents are substituted at the 2- and 6-positions of the phenyl group is particularly preferably used because the above-mentioned properties are stronger. The structure of the N-substituted-chloroacetanilide represented by the general formula [] can be confirmed by the following means. (b) By measuring the infrared absorption spectrum (IR), it is possible to observe an absorption based on the CH bond in the vicinity of 3150-2800 cm -1 and a characteristic absorption based on the carbonyl bond of the amide group in the vicinity of 1680-1660 cm -1 . I can do it. (b) Measuring the mass spectrum (MS) and calculating the composition formula corresponding to each peak observed (generally a value expressed as m/e, which is the ion mass number m divided by the ion charge number e). Accordingly, it is possible to know the molecular weight of the compound subjected to measurement and the bonding mode of each atomic group within the molecule. In other words, the sample subjected to measurement is expressed by the general formula [] When expressed as The molecular weight of can be determined. Furthermore, regarding the N-substituted-chloroacetanilide represented by the general formula [], M -Cl, M -
COCH2Cl and A characteristic strong peak corresponding to is observed, and the binding mode of the molecule can be known. (c) 1 H-Nuclear Magnetic Resonance Spectrum ( 1 H-NMR)
By measuring , it is possible to know the bonding mode of hydrogen atoms present in the N-substituted chloroacetanilide represented by the general formula []. 1 H-NMR (δ, ppm:
(based on tetramethylsilane, in deuterated chloroform solvent), N-[2'-(5'-bromo)
-thienylmethyl]-N-chloroaceto-2,
Figure 1 shows a 1 H-NMR diagram of 6-dimethylanilide. The analysis results are as follows. In other words, a singlet corresponding to 6 protons is observed at 2.0 ppm, which is the 2nd line of the phenyl group.
It can be attributed to the methyl group (d) substituted at the 6-position. A singlet corresponding to two protons was observed at 3.6 ppm, and this can be attributed to the methylene group (h) in the chloroacetyl group.
A singlet corresponding to two protons was observed at 4.75 ppm, and this can be attributed to the methylene group (c). A quartet corresponding to two protons was observed at 6.67 ppm, and this can be attributed to protons (a) and (b) substituted on the thiophene ring. A multiplet corresponding to three protons was observed at 6.95 to 7.30 ppm, and this can be attributed to protons (e), (h), and (g) substituted with phenyl groups. To summarize the 1 H-NMR characteristics of the N-substituted chloroacetanilide represented by the above general formula [], the methylene proton of the chloroacetyl group usually appears as a singlet around 3.6 to 3.8 ppm,
When R 4 is a hydrogen atom, the methylene proton of the aminomethylene group is 4.7 to 5.0 ppm as a singlet.
(However, if there are substituents asymmetrically at the 2 and 6 positions on the aniline side, a double line may appear), if R 4 is an alkyl group, the methine of the aminomethine group proton is
From 5.7 to 6.7 ppm, the proton on the thiophene ring side is
5.8 to 7.4ppm, and the proton on the benzene ring side is 6.0
It tends to show a characteristic peak at ~7.7ppm. (d) Carbon, hydrogen, nitrogen, sulfur,
By determining the weight percent of each element and halogen, and subtracting the sum of the weight percent of each confirmed element from 100, the weight percent of oxygen can be calculated.
Therefore, the compositional formula can be determined. In addition, N-substituted-chloroacetanilide is
R 1 , R 2 , R 3 , R 4 , R 5 in the general formula [],
Although their properties differ somewhat depending on the type of R 6 and R 7 , they are generally pale yellow or yellow viscous liquids or solids at room temperature and pressure, and many have extremely high boiling points. More specifically, as shown in the synthesis examples described later, the boiling point of the above compound tends to increase as the molecular weight increases, like general organic compounds. The compound is soluble in common organic solvents such as benzene, ether, alcohol, chloroform, carbon tetrachloride, acetonitrile, N,N-dimethylformamide, and dimethyl sulfoxide, but almost insoluble in water. The method for producing the N-substituted chloroacetanilide represented by the general formula [] is not particularly limited. A typical manufacturing method is described below. General formula [], (However, in the formula, R 1 , R 2 and R 3 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups or alkylthioalkyl groups, and R 4 represents a hydrogen atom or an alkyl R 5 , R 6 and R 7 are the same or different hydrogen atoms, halogen atoms, alkyl groups,
Indicates an alkenyl group, an alkynyl group, an alkoxy group, or an alkylthio group. ) Aniline derivatives represented by and the general formula
ClCH 2 COX (X represents a halogen atom)
The N-substituted-chloroacetanilide represented by the general formula [] can be obtained by reacting with the chloroacetyl halide represented by the formula []. The aniline derivative represented by the above general formula [], which is a raw material, can be obtained by any method. In the reaction between the compound represented by the above general formula [] and chloroacetyl halide, the molar ratio of both compounds may be appropriately determined as necessary, but it is usually the same molar ratio or a slight excess molar amount of chloroacetyl halide. It is common to use Further, in the above reaction, hydrogen halide is produced as a by-product. This hydrogen halide reacts with the aniline derivative represented by the general formula [] in the reaction system, causing a decrease in the yield of the product, so a hydrogen halide scavenger is usually allowed to coexist in the reaction system. is preferred. The hydrogen halide scavenger is not particularly limited, and any known one can be used. Examples of the scavenger that are generally suitably used include trialkylamines such as trimethylamine, triethylamine, and tripropylamine, pyridine, sodium alllate, and sodium carbonate. It is generally preferable to use an organic solvent in the reaction. Examples of solvents preferably used include benzene, toluene, xylene,
Aliphatic or aromatic hydrocarbons or halogenated hydrocarbons such as hexane, heptane, petroleum ether, chloroform, methylene chloride, and ethylene chloride; Ethers such as diethyl ether, dioxane, and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone ; Nitriles such as acetonitrile; N,N-dimethylformamide,
Examples include N,N-dialkylamides such as N,N-diethylformamide; dimethyl sulfoxide and the like. The order of addition of the raw materials in the reaction is not particularly limited, but generally, the aniline derivative represented by the general formula [] is dissolved in a solvent, the mixture is charged into a reactor, and the chloroacetyl halide dissolved in the solvent is added under stirring. Good. Of course, it is also possible to continuously add raw materials to the reaction system and take out the produced reactants continuously from the reaction system. The temperature in the reaction can be selected from a wide range, generally -20°C to 150°C, preferably 0°C to 120°C.
It is sufficient to choose from the range of °C. Reaction time varies depending on the type of raw material, but is usually 5 minutes to 10 days.
Preferably, it is sufficient to select from the range of 1 to 40 hours. Further, during the reaction, it is preferable to perform stirring. The method for isolating and purifying the desired product, ie, the N-substituted chloroacetanilide represented by the above general formula [], from the reaction system is not particularly limited, and any known method can be employed. For example, the reaction solution is cooled or allowed to cool naturally to return to room temperature or near room temperature, the reaction solvent and the remaining hydrogen halide scavenger are distilled off, and the residue is extracted with benzene. In the above operation, the salt and high molecular weight compound produced from the by-produced hydrogen halide and the hydrogen halide scavenger are separated. The benzene layer is dried with a desiccant such as Glauber's salt or calcium chloride, and then benzene is distilled off and the residue is vacuum distilled to obtain the desired product.
In addition to isolation and purification by vacuum distillation, it can also be purified by chromatography or, if the product is a solid, by recrystallization from a solvent such as hexane. As another method for producing the N-substituted-chloroacetanilide represented by the general formula [], the following method is also preferably employed. general formula (However, in the formula, R 1 , R 2 and R 3 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups, and alkylthioalkyl groups, and R 4 represents a hydrogen atom or an alkyl group, and X represents a halogen atom.)
Substituted-thiophene represented by and the general formula (However, in the formula, R 5 , R 6 and R 7 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, and alkylthio groups.) The N-substituted chloroacetanilide represented by the above general formula [] can also be obtained by reaction. The substituted thiophene and the chloroacetanilide used as raw materials can be obtained by any method. In addition, the conditions and isolation and purification method for carrying out the reaction are the same as the conditions and isolation and purification method used in the reaction of the aniline derivative represented by the general formula [] and chloroacemol halide. Almost similar conditions can be adopted. The N-substituted chloroacetanilide represented by the above general formula [] has a wide herbicidal spectrum against annual weeds such as field weeds and Japanese grasshoppers that occur in rice fields, as well as perennial weeds such as bulrushes and omodaka, and It is an excellent herbicide that can efficiently control paddy rice without causing chemical damage. The other component of the herbicidal composition of the present invention is a white squid. The white squid is not particularly limited, and known ones can be used as they are. For example, "Practical Handbook of Additives for Plastics and Rubber" published by Kagaku Kogyosha.
(Published August 10, 1970) Artificially produced silicic acid and silicate as shown on pages 541 to 560 can be suitably used. Particularly suitable are hydrated silicic acid produced by a wet method, and whica called anhydrous silicic acid produced by a dry method. Among silicates, fine powder calcium silicate is preferred. These white squids may be used alone or in a mixture of different types. As mentioned above, the herbicidal composition of the present invention consists of a mixture containing an N-substituted chloroacetanilide represented by the general formula [] and a whica,
In the herbicidal composition of the present invention containing an N-substituted chloroacetanilide and a whiker, excellent herbicidal effects can be obtained in an extremely wide range of usage ratios of the N-substituted chloroacetanilide and a whiker. However, in general, it is preferable to select the amount of whiter to be used in a range of 15 to 400 times, preferably 30 to 200 times, the weight of the N-substituted chloroacetanilide. Although some of the herbicide compositions of the present invention exhibit their effects when used as granules, the method for producing the granules is not particularly limited, and any known method can be used as is. For example, in addition to the N-substituted-chloroacetanilide and the whicas, surfactants, carriers, and adjuvants used to improve properties such as disintegration (generally casein, polymer compounds such as gelatin, glue, cellulose)
Mixtures such as these can be appropriately selected and used as long as the effects of the present invention are not impaired. For example, the following method can be suitably employed.
That is, 1 part by weight of N-substituted chloroacetanilide, a surfactant, and water are thoroughly kneaded, and then a carrier containing a whica and a surfactant are added,
There is a method of obtaining granules by stirring well, extruding to a predetermined particle size, and drying. The carrier may be appropriately selected from known carriers, but examples of carriers that are generally preferred include clays represented by kaolinite group, montmorillonite group, attapulgite group, ziecrite, etc.; talc, mica, and leaves. Waxite, pumice, vermiculite, gypsum, calcium carbonate, dolomite, magnesium diatomaceous earth, lime, apatite,
Gelite; vegetable organic substances such as soybean flour, tobacco flour, walnut flour, wheat flour, wood flour, crystalline cellulose;
Synthetic or natural polymer compounds such as coumaron resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, copal gum, and dammar gum; Waxes such as carnauba wax and beeswax, or solid carriers of urea, etc. can be mentioned. Liquid carriers include paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, and white oil; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, and methylnaphthalene; carbon tetrachloride, and chloroform. , trichlorethylene, monochlorobenzene, o-chlorotoluene; ethers such as dioxane, tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone; ethyl acetate, amyl acetate, Esters such as ethylene glycol acetate, diethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate; Alcohols such as methanol, n-hexanol, ethylene glycol, diethylene glycol; ethylene glycol phenyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether, etc. Ether alcohols; polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. Furthermore, as the surfactant, nonionic, cationic, anionic, and amphoteric surfactants are used, but nonionic and/or anionic surfactants are usually preferably used. . Suitable nonionic surfactants include, for example, those obtained by polymerizing and adding ethylene oxide to higher alcohols such as lauryl alcohol, stearyl alcohol, and oleyl alcohol; and those obtained by polymerizing and adding ethylene oxide to alkyl phenols such as isooctylphenol and nonylphenol. Products obtained by polymerizing and adding ethylene oxide to alkyl phenols such as isooctylphenol and nonylphenol; Products obtained by polymerizing and adding ethylene oxide to alkylnaphthols such as butylnaphthol and octylnaphthol; Products such as palmitic acid, stearic acid, and oleic acid. Products obtained by polymerizing and adding ethylene oxide to higher fatty acids; Stearyl phosphoric acid and dilauryl phosphoric acid are also products obtained by polymerizing and adding ethylene oxide to mono- or dialkyl phosphoric acid; Products obtained by polymerizing and adding ethylene oxide to amines such as dodecylamine and stearic acid amide. Examples include higher fatty acid esters of polyhydric alcohols such as sorbitan and those obtained by polymerizing and adding ethylene oxide to them; those obtained by polymerizing and adding ethylene oxide and propylene oxide; and esters of polyhydric fatty acids and alcohols such as dioctyl succinate. Suitable anionic surfactants include, for example, alkyl sulfate salts such as sodium lauryl sulfate and oleyl alcohol sulfate amine salt; alkyl sulfonate salts such as sodium sulfosuccinate dioctyl ester and sodium 2-ethylhexene sulfonate. ; Aryl sulfonates such as sodium isopropylnaphthalene sulfonate, sodium methylene bisnaphthalene sulfonate, sodium lignin sulfonate, and sodium dodecylbenzenesulfonate; and phosphates such as sodium tripolyphosphate. (Actions and Effects) The herbicidal composition of the present invention exhibits significantly more stable medicinal efficacy than a composition that does not contain white mosquitoes or a composition that contains a small amount of white mosquito, and furthermore, Even if the content of substituted chloroacetanilide is reduced, the same or higher herbicidal effect can be achieved. However, it is currently not clear what kind of action mechanism causes these effects. Considering the phenomenon that granules mixed with white powder have different disintegration and spreadability in water compared to granules that do not contain white powder, it is possible that this difference in disintegration and spreadability has some influence on biological effects. It is estimated that the The herbicide composition of the present invention is effective even when treated before and after germination of herbs, and is also highly effective in soil treatment and foliage treatment. It is useful in a wide range of areas where it can be applied, including rice fields, fields of various grains, legumes, cotton, vegetable crops, orchards, lawns, pastures, tea gardens, mulberry gardens, forests, non-agricultural lands, etc. . Furthermore, the herbicidal composition of the present invention fully satisfies the properties required of a herbicide, and is extremely useful. (Examples) Hereinafter, the herbicidal composition of the present invention will be explained using specific examples, but the present invention is not limited to these examples. Synthesis of N-substituted-chloroacetanilide Synthesis example 1 N-[2'-(5'-bromo)-thienylmethyl]-
2,6-dimethylaniline 1.81g (6.14×
10 -3 mole) was dissolved in 40 ml of benzene, 0.81 g (7.98 x 10 -3 mole) of triethylamine was added, and the mixture was placed in ice water. Then chloracetyl chloride 0.83
g (7.37×10 −3 mole) in benzene solution (15 ml) was gradually added. After stirring for 3 hours, the mixture was heated at 50°C for 1 hour. After cooling the reaction mixture to room temperature,
It was washed successively with 50 ml of water, 50 ml of 2N hydrochloric acid, and then 50 ml of water, and the benzene layer was dried over anhydrous sodium sulfate. Thereafter, it was purified by column chromatography to obtain 1.13 g of a yellow solid. As a result of measuring the infrared absorption spectrum of this product, it showed an absorption based on the C-H bond at 3110 to 2900 cm -1 and a strong absorption based on the carbonyl bond of the amide group at 1670 cm -1 . Its elemental analysis values are C48.43%, H4.05%, N3.99%,
Calculated value for C 15 H 15 NSOBrCl (372.71)
It matched well with C48.20%, H4.32%, and N3.75%. In addition, when mass spectra were measured, m/
Molecular ion peak corresponding to molecular weight (M
), the beak corresponding to M −Cl at m/e336,
A peak corresponding to M-COCH 2 Cl at m/e293,
m/e143 (100%) The corresponding peaks are shown. Furthermore, the 1 H-nuclear magnetic resonance spectrum is as shown as a specific example in the specification. From the above results, it is clear that the isolated product is N-[2'-(5'-
bromo)-thienylmethyl]-N-chloroaceto-
It became clear that it was 2,6-dimethylanilide (hereinafter abbreviated as compound (1)). The yield is N
-[2'-(5'-bromo)-thienylmethyl]-2,6
-49.5% (3.04% x
10 -3 mole). Synthesis Example 2 The properties, physical properties (boiling point), characteristic absorption values in the infrared spectrum, and elemental analysis results of N-substituted-chloroacetanilide synthesized in the same manner as in Synthesis Example 1 are summarized in Table 1. Furthermore, the general formula in Table 1 is the general formula [] Corresponding to, A is
【式】 はR4を、Ｄは[Formula] is R 4 , D is
【式】を意味する。It means [formula].
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
製剤例 １
前記第１表化合物No.39の化合物１重量部、含水
珪酸〔トクシールＰ（徳山曹達(株)製、商品名）〕50
重量部、ジオクチルサクシネート４重量部、トリ
ポリりん酸ソーダ４重量部、ベントナイト25重量
部およびタルク16重量部をよく混合粉砕し、水を
加えて混練した後造粒乾燥し、14〜32メツシユに
整流して粒剤を得た。
製剤例 ２
珪酸カルシウム〔フローライトＲ（徳山曹達(株)
製、商品名）〕30重量部、ベントナイト15重量部、
タルク50重量部およびトリポリりん酸ソーダ５重
量部を粉砕混合し、加水、混練後造粒乾燥し、粒
状物とした。この粒状物99重量部に前記第１表化
合物No.40の化合物を１重量部含浸させて粒剤とし
た。
製剤例 ３
前記第１表化合物No.50の化合物５重量部、含水
珪酸〔カープレツクス＃80（塩野義製薬(株)製、商
品名）〕60重量部、リグニンスルホン酸ソーダ３
重量部、ジオクチルサクシネート１重量部、ベン
トナイト20重量部、タルク11重量部をよく混合粉
砕し、水を加えて混練した後造粒乾燥し、14〜32
メツシユに整粒して粒剤を得た。
比較製剤例 １
製剤例１で用いた含水珪酸に代りクレーを用い
た以外は製剤例１と同様に製剤して粒剤を得た。
比較製剤例 ２
製剤例２で用いた珪酸カルシウムに代りケイソ
ウ土を用いた以外は製剤例２と同様に製剤して粒
剤を得た。
比較製剤例 ３
製剤例３で用いた含水珪酸60重量部に代り炭酸
カルシウム20重量部を用い、また同タルク11重量
部に代りタルク51重量部を用いた以外は製剤例３
と同様に製剤して粒剤を得た。
実施例
8850分の１アルコール相当のワグナーポツト
に、加水混練した水田土壌を充填し、土壌表層に
ノビエの種子を播種し、約３cmの湛水条件とし、
20〜25℃のガラス室内で育成し、14日後（ノビエ
が約２葉期の時期）に、製剤例に準じて調製した
粒剤を所定量（３Kg／10a）処理した。その後ガ
ラス室内で育成し、薬剤処理後21日目に除草効果
を調査した。その結果は第２表に示した。尚第２
表に於ける化合物No.は第１表に於いて確認した化
合物No.の化合物を示す。また除草効果は次の６段
階方式で評価した。
除草効果
抑草率（％）
５：100（完全枯死）
４：75〜99
３：50〜74
２：25〜49
１：１〜24
０：０（全く効果が認められない。）[Table] Formulation Example 1 1 part by weight of Compound No. 39 in Table 1 above, hydrated silicic acid [Tokusil P (manufactured by Tokuyama Soda Co., Ltd., trade name)] 50
parts by weight, 4 parts by weight of dioctyl succinate, 4 parts by weight of sodium tripolyphosphate, 25 parts by weight of bentonite and 16 parts by weight of talc were thoroughly mixed and pulverized, water was added and kneaded, and then granulated and dried to form 14 to 32 meshes. The mixture was rectified to obtain granules. Formulation example 2 Calcium silicate [Fluorite R (Tokuyama Soda Co., Ltd.)
product name)] 30 parts by weight, bentonite 15 parts by weight,
50 parts by weight of talc and 5 parts by weight of sodium tripolyphosphate were ground and mixed, added with water, kneaded, and then granulated and dried to obtain granules. 99 parts by weight of the granules were impregnated with 1 part by weight of the compound No. 40 in Table 1 to prepare granules. Formulation Example 3 5 parts by weight of Compound No. 50 in Table 1, 60 parts by weight of hydrated silicic acid [Carplex #80 (trade name, manufactured by Shionogi & Co., Ltd.)], 3 parts by weight of sodium lignin sulfonate
parts by weight, 1 part by weight of dioctyl succinate, 20 parts by weight of bentonite, and 11 parts by weight of talc are thoroughly mixed and pulverized, water is added, kneaded, and granulated and dried.
Granules were obtained by sizing into mesh. Comparative Formulation Example 1 Granules were prepared in the same manner as Formulation Example 1 except that clay was used in place of the hydrated silicic acid used in Formulation Example 1. Comparative Formulation Example 2 Granules were prepared in the same manner as Formulation Example 2 except that diatomaceous earth was used in place of the calcium silicate used in Formulation Example 2. Comparative Formulation Example 3 Formulation Example 3 except that 20 parts by weight of calcium carbonate was used instead of 60 parts by weight of hydrated silicic acid used in Formulation Example 3, and 51 parts by weight of talc was used instead of 11 parts by weight of talc.
Granules were prepared in the same manner as above. Example A Wagner pot containing 1/8850 alcohol equivalent was filled with water-mixed paddy soil, seeds of wild grass were sown on the surface layer of the soil, and the soil was flooded to a depth of about 3 cm.
The plants were grown in a glass room at 20 to 25° C., and 14 days later (when the wild plants were at about the two-leaf stage), they were treated with a predetermined amount (3 kg/10 a) of granules prepared according to the formulation example. The plants were then grown in a glass room, and the herbicidal effect was investigated on the 21st day after the chemical treatment. The results are shown in Table 2. Furthermore, the second
Compound No. in the table indicates the compound No. confirmed in Table 1. In addition, the herbicidal effect was evaluated using the following 6-level method. Weeding effect Weed suppression rate (%) 5:100 (complete death) 4:75-99 3:50-74 2:25-49 1:1-24 0:0 (no effect observed at all)
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
比較例
前記実施例において用いた粒剤に代り比較製剤
例１〜３で得た粒剤を用いた以外は実施例と同様
に実施した。その結果は第３表に示した。[Table] Comparative Example The same procedure as in the Example was carried out except that the granules obtained in Comparative Formulation Examples 1 to 3 were used in place of the granules used in the above Examples. The results are shown in Table 3.
第１図は合成例１で得られたＮ−置換−クロロ
アセトアニリドの1H−NMRのチヤートを示す。
FIG. 1 shows a 1 H-NMR chart of N-substituted-chloroacetanilide obtained in Synthesis Example 1.
Claims (1)
素原子、ハロゲン原子、アルキル基、アルコキシ
基、アルキルチオ基、アルコキシアルキル基、又
はアルキルチオアルキル基を示し、R4は水素原
子又はアルキル基を示し、R5、R6及びR7は同種
又は異種の水素原子、ハロゲン原子、アルキル
基、アルケニル基、アルキニル基、アルコキシ
基、又はアルキルチオ基を示す。） で表わされるＮ−置換−クロロアセトアニリドに
対して、ホワイトカーボン類を重量で15〜400倍
混合することを特徴とする除草剤組成物。[Claims] 1. The following general formula (However, in the formula, R 1 , R 2 and R 3 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups, or alkylthioalkyl groups, and R 4 represents a hydrogen atom or N - substituted- A herbicide composition characterized in that white carbon is mixed 15 to 400 times the weight of chloroacetanilide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26746684A JPS61145101A (en) | 1984-12-20 | 1984-12-20 | Herbicide composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26746684A JPS61145101A (en) | 1984-12-20 | 1984-12-20 | Herbicide composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61145101A JPS61145101A (en) | 1986-07-02 |
| JPH0471041B2 true JPH0471041B2 (en) | 1992-11-12 |
Family
ID=17445228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26746684A Granted JPS61145101A (en) | 1984-12-20 | 1984-12-20 | Herbicide composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61145101A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59157083A (en) * | 1983-02-25 | 1984-09-06 | Tokuyama Soda Co Ltd | N-substituted-chloroacetanilide and its preparation |
-
1984
- 1984-12-20 JP JP26746684A patent/JPS61145101A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59157083A (en) * | 1983-02-25 | 1984-09-06 | Tokuyama Soda Co Ltd | N-substituted-chloroacetanilide and its preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61145101A (en) | 1986-07-02 |
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