JPS6128642B2 - - Google Patents
Info
- Publication number
- JPS6128642B2 JPS6128642B2 JP54011227A JP1122779A JPS6128642B2 JP S6128642 B2 JPS6128642 B2 JP S6128642B2 JP 54011227 A JP54011227 A JP 54011227A JP 1122779 A JP1122779 A JP 1122779A JP S6128642 B2 JPS6128642 B2 JP S6128642B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- compound
- hydroxypyrazole
- weeds
- 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
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 2
- -1 methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy Chemical group 0.000 description 59
- 150000001875 compounds Chemical class 0.000 description 45
- 241000196324 Embryophyta Species 0.000 description 43
- 239000004009 herbicide Substances 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000002689 soil Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 230000002363 herbicidal effect Effects 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- 241000234653 Cyperus Species 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- 244000184734 Pyrus japonica Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 5
- 239000000920 calcium hydroxide Substances 0.000 description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 240000007019 Oxalis corniculata Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000208838 Asteraceae Species 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 240000008444 Celtis occidentalis Species 0.000 description 3
- 235000018962 Celtis occidentalis Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 241001076438 Oxya japonica Species 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001266 acyl halides Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 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
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- JYUXDXWXTPSAEL-UHFFFAOYSA-N 1,4-dioxane;oxolane Chemical compound C1CCOC1.C1COCCO1 JYUXDXWXTPSAEL-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
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 240000004731 Acer pseudoplatanus Species 0.000 description 2
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000219317 Amaranthaceae Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000219321 Caryophyllaceae Species 0.000 description 2
- KZGVRGZLCUDNAB-UHFFFAOYSA-N Cc1ccccc1C(=O)c2c(C)nn(c2O)c3ccccc3 Chemical compound Cc1ccccc1C(=O)c2c(C)nn(c2O)c3ccccc3 KZGVRGZLCUDNAB-UHFFFAOYSA-N 0.000 description 2
- PAYUZNASXZTNFC-UHFFFAOYSA-N Cc1nn(c(O)c1C(=O)c1ccc(Cl)cc1)-c1ccccc1 Chemical compound Cc1nn(c(O)c1C(=O)c1ccc(Cl)cc1)-c1ccccc1 PAYUZNASXZTNFC-UHFFFAOYSA-N 0.000 description 2
- MXUDACDLCWMNPA-UHFFFAOYSA-N Cc1nn(c(O)c1C(=O)c2ccc(Cl)cc2)c3ccc(Cl)cc3 Chemical compound Cc1nn(c(O)c1C(=O)c2ccc(Cl)cc2)c3ccc(Cl)cc3 MXUDACDLCWMNPA-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- SENFJXMAKBODHY-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)C(=O)C=1C(=NN(C=1O)C1=CC=CC=C1)C Chemical compound ClC1=C(C=CC(=C1)Cl)C(=O)C=1C(=NN(C=1O)C1=CC=CC=C1)C SENFJXMAKBODHY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 240000003173 Drymaria cordata Species 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UDBIAGILKCRUNB-UHFFFAOYSA-N OC1=C(C(=NN1C1=CC=CC=C1)C)C(=O)C1=CC=C(C=C1)C Chemical compound OC1=C(C(=NN1C1=CC=CC=C1)C)C(=O)C1=CC=C(C=C1)C UDBIAGILKCRUNB-UHFFFAOYSA-N 0.000 description 2
- 235000016499 Oxalis corniculata Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000006485 Platanus occidentalis Nutrition 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 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
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000013078 crystal Substances 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
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000013312 flour Nutrition 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
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 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
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-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
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-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
- CJUUXVFWKYRHAR-UHFFFAOYSA-M 1-Naphthaleneacetic acid sodium salt Chemical compound [Na+].C1=CC=C2C(CC(=O)[O-])=CC=CC2=C1 CJUUXVFWKYRHAR-UHFFFAOYSA-M 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-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
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- 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
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 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
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 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
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 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
- 238000002156 mixing Methods 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
- 239000012053 oil suspension Substances 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
- 239000002420 orchard Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000013459 phenoxy herbicide Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000014774 prunus Nutrition 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 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
- 238000003892 spreading Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、一般式
(式中、R1が低級アルキル基を示すとき、R2
はフエニル基またはハロゲン置換フエニル基を示
し、R1がフエニル基またはホルミル基を示すと
き、R2は低級アルキル基を示す。
Xは低級アルキル基、低級アルコキシ基、ニト
ロ基またはハロゲン原子を示し、nは0,1また
は2を示し、nが2のときXは互いに同一もしく
は異なつてもよい。)を有する化合物、その塩ま
たはその脂肪族もしくは芳香族カルボン酸または
スルホン酸エステルを有効成分とする除草剤に関
するものである。
前記一般式()の化合物は次に示すような互
変異性として存在することができる。
(式中、R1,R2,Xおよびnは前述したもの
と同じ)
前記一般式()において、R1およびR2の一
方は好適にはメチル、エチル、n−プロピル、イ
ソプロピル、n−ブチルまたはイソブチルのよう
な炭素数1乃至4個を有する直鎖状または分枝鎖
状の低級アルキル基を示す。Xは好適には上記に
例示したのと同様な炭素数1乃至4個を有する直
鎖状または分枝鎖状の低級アルキル基;メトキ
シ、エトキシ、n−プロポキシ、イソプロポキ
シ、n−ブトキシまたはイソプトキシのような炭
素数1乃至4個を有する直鎖状または分枝鎖状の
低級アルコキシ基;ニトロ基;塩素、臭素、弗素
または沃素のようなハロゲン原子を示す。
前記一般式()の化合物の塩としては、例え
ばナトリウム、カリウム、カルシウム、マグネシ
ウム、アルミニウム、鉄、マンガン、亜鉛、ニツ
ケル、コバルトまたは銅のような1価ないし3価
の金属イオンとの塩;〔Cu(H2O)2〕++,〔Mn
(H2O)2〕++,〔Ni(H2O)4〕++,〔Al(OH)〕++,
〔Zn(OH)〕+,〔Cu(OH)〕+,〔Cu(NH3)2〕++ま
たは〔Co(NH2CH2CH2NH2)〕++のような錯イオ
ンとの塩;N+H4,N+H(CH3)3,N+H2
(C2H5)2,N+H3CH(CH3)2,N+H3CH2CH2OH
またはN+H3CH3CH2CH2OC2H5のようなアンモ
ニウムイオンとの塩;塩酸硫酸、硝酸または臭化
水素酸などの鉱酸との塩が含まれる。
前記一般式()の化合物の有機酸エステルは
ピラゾール環の5位において形成され、分解によ
り一般式()の化合物を生成する有機酸とのエ
ステルであればよい。このような有機酸として
は、
(1) 脂肪酸または芳香族カルボン酸、例えば
式 R3COOH
上記式中R3はメチル、エチル、n−プロピ
ル、イソプロピル、n−ブチル、イソブチルま
たはtert−ブチルのような炭素数1乃至4個を
有する直鎖状または分枝鎖状のアルキル基;あ
るいはフエニル、2−もしくは4−ニトロフエ
ニル、2−、3−もしくは4−トリル、2−も
しくは4−クロロフエニル、2−もしくは4−
ブロモフエニル、2,4−ジクロロフエニル、
2,4,6−トリクロロフエニルまたは2−ク
ロロ−4−ニトロフエニルのようなニトロ、ハ
ロゲンおよび(または)炭素数1乃至4個、特
に1個を有するアルキル基を置換分として1乃
至3個有するか有しないフエニル基を示す。
(2) スルホン酸、例えば
式 R4−SO2−OH
上記式中R4はメチル、エチル、n−プロピ
ル、イソプロピル、n−ブチルまたはイソブチ
ルのような炭素数1乃至4個を有する直鎖状ま
たは分枝鎖状の低級アルキル基;あるいはメチ
ル、エチル、n−プロピル、イソプロピル、n
−ブチルまたはイソブチルのような炭素数1乃
至4個特に1または2個を有する直鎖状または
分枝鎖状のアルキルまたはクロロのようなハロ
ゲンを置換分として有するか有しないフエニル
基を示す。
本発明の除草剤において用いられる前記一般式
()を有する化合物を例示すれば次のとおりで
ある(なお、化合物番号は以下の記載において参
照される。)
化合物番号 化 合 物
1 1−フエニル−3−メチル−4−ベンゾイル
−5−ヒドロキシピラゾール
2 1−(4−クロロフエニル)−3−メチル−−
4−ベンゾイル−5−ヒドロキシピラゾール
3 1−(4−クロロフエニル)−3−メチル−4
−(2−クロロベンゾイル)−5−ヒドロキシピ
ラゾール
4 1−(4−クロロフエニル)−3−メチル−4
−(4−クロロベンゾイル)−5−ヒドロキシピ
ラゾール
5 1−フエニル−3−メチル−4−(2−クロ
ロベンゾイル)−5−ヒドロキシピラゾール
6 1−フエニル−3−メチル−4−(4−クロ
ロベンゾイル)−5−ヒドロキシピラゾール
7 1−フエニル−3−メチル−4−(2−メト
キシベンゾイル)−5−ヒドロキシピラゾール
8 1−フエニル−3−メチル−4−(4−ニト
ロベンゾイル)−5−ヒドロキシピラゾール
9 1−(4−クロロフエニル)−3−メチル−4
−(4−ニトロベンゾイル)−5−ヒドロキシピ
ラゾール
10 1−(4−クロロフエニル)−3−メチル−4
−(2−メトキシベンゾイル)−5−ヒドロキシ
ピラゾール
11 1−(2−クロロフエニル)−3−メチル−4
−(2−クロロベンゾイル)−5−ヒドロキシピ
ラゾール
12 1−フエニル−3−メチル−4−ベンゾイル
−5−ヒドロキシピラゾール アルミニウム塩
13 1−フエニル−3−メチル−4−o−トルオ
イル−5−ヒドロキシピラゾール アルミニウ
ム塩
14 1−フエニル−3−メチル−4−o−トルオ
イル−5−ヒドロキシピラゾール
15 1−フエニル−3−メチル−4−p−トルオ
イル−5−ヒドロキシピラゾール
17 1−フエニル−3−メチル−4−(2,4−
ジクロロベンゾイル)−5−ヒドロキシピラゾ
ール
18 5−アセトキシ−4−(2,4−ジクロロベ
ンゾイル)−3−メチル−1−フエニルピラゾ
ール
19 4−(2,4−ジクロロベンゾイル)−3−メ
チル−1フエニル−5−ピラゾリルp−トルエ
ンスルホネート
20 1−フエニル−3−メチル−4−(3−メチ
ル−6−ニトロベンゾイル)−5−ヒドロキシ
ピラゾール
21 5−ヒドロキシ−1−メチル−3−フエニル
−4−(4−ニトロベンゾイル)ピラゾール
22 5−ヒドロキシ−1−メチル−3−フエニル
−4−(2−メトキシベンゾイル)ピラゾール
23 4−(2−クロロベンゾイル)−5−ヒドロキ
シ−1−メチル−3−フエニルピラゾール
24 4−(4−クロロベンゾイル)−5−ヒドロキ
シ−1−メチル−3−フエニルピラゾール
25 4−(3,5−ジメトキベンゾイル)−5−ヒ
ドロキシ−1−メチル−3−フエニルピラゾー
ル
29 4−ベンゾイル−1−メチル−3−フエニル
−5−ヒドロキシピラゾール アルミニウム塩
30 1−メチル−3−フエニル−4−ベンゾイル
−5−ヒドロキシピラゾール
34 4−(2,4−ジクロロベンゾイル)−5−ヒ
ドロキシ−1−メチル−3−ピラゾリルアルデ
ヒド
35 1−メチル−3−フエニル−4−(2,4−
ジクロロベンゾイル)−5−ヒドロキシピラゾ
ール
36 5−ヒドロキシ−4−(5−メチル−2−ニ
トロベンゾイル)−1−メチル−3−フエニル
ピラゾール
上記の化合物は、化合物番号1,5,8で示さ
れる化合物を除き、いずれも文献未載の新規化合
物であり、前記一般式()を有する化合物、そ
の塩およびその有機酸エステルは次の方法により
製造される。
(1) 一般式()を有する化合物は、次式に示す
ように、5−ピラゾロン誘導体()に触媒の
存在下、アシルハライド()を反応させるこ
とによつて容易に製造される。
(式中R1,R2,Xおよびnは前述したもの
と同一である。)
上記の反応は溶剤の存在下で好適に行なわれ
る。使用される溶剤としては本反応に関与しな
ければ特に限定はなく、例えばジエチルエーテ
ル、テトラヒドロフラン、ジエチルエーテル−
ジオキサン、テトラヒドロフラン−ジオキサン
などのエーテル類またはこれらの混合溶剤;ジ
クロロメタン、四塩化炭素などのハロゲン化炭
化水素類;イソプロパノール、イソブタノー
ル、tert−ブタノールなどの2級または3級ア
ルコール類等があげられ、特にエーテル類およ
び2級アルコール類が好適に使用される。反応
はまた、触媒の存在下で好適に行なわれる。使
用される触媒としては、水酸化カルシウムなど
のアルカリ土類金属の水酸化物、塩化アルミニ
ウムなどの金属塩化物等があげられ、特に水酸
化カルシウムが好適に使用される。触媒の使用
量は好適には式()の原料化合物1モルに対
して1〜2モルが使用される。反応温度は特に
限定はなく室温乃至溶剤の還流温度で行なわ
れ、特に好適には溶剤の還流温度近くで行なわ
れる。反応時間は主に反応温度、使用される試
薬の種類によつて異なるが約1乃至10時間であ
る。
また、上記の反応において使用されるアシル
ハライドは、例えば酸クロライドまたは酸ブロ
マイドが用いられる。
反応終了後、目的化合物は常法に従つて反応
混合物から採取される。なお、式()の原料
化合物はベリヒテ(Ber.)43,2106(1910)に
記載の方法に準じて製造される。
(2) 一般式()を有する化合物は、次式に示す
ように、相当する5−ハロゲノビラゾール誘導
体()を水酸化ナトリウム、水酸化カリウム
のようなアルカリ金属水酸化物と加熱すること
によつても得られる。
(式中R1,R2,Xおよびnは前述したもの
と同意義を示す。)
上記の反応は水を溶剤として使用することが
できる。また、水と有機溶剤との混合溶剤を使
用することもでき、そのような有機溶剤として
は例えばテトラヒドロフラン、ジオキサンなど
のエーテル類;メタノール、エタノールなどの
アルコール類があげられる。反応温度は特に限
定はなく、室温乃至溶剤の還流温度で行なわ
れ、特に好適には溶剤の還流温度近くで行なわ
れる。反応時間は主に反応温度、使用される試
薬の種類によつて異なるが約1乃至10時間であ
る。
なお、式()の原料化合物は、ベリヒテ
(Ber.)50,737(1917)および英国特許第
1268608号明細書に記載の方法に準じて製造さ
れる。
(3) 一般式()を有する化合物の有機酸エステ
ル()や次式に示すように式()の化合物
にアシル化剤を反応させることにより容易に製
造される。
(式中R1,R2,Xおよびnは前述したもの
と同意義を示し、R5は有機酸残基を示す。)
上記の反応は溶剤の存在下で好適に行なわれ
る。使用される溶剤としては本反応に関与しな
ければ特に限定はなく、例えばジエチルエーテ
ル、テトラヒドロフラン、ジエチルエーテル−
ジオキサン、テトラヒドロフラン−ジオキサン
などのエーテル類またはこれらの混合溶剤;ベ
ンゼン、トルエン、キシレンなどの芳香族炭化
水素類;ジクロロメタン、クロロホルム、四塩
化炭素などのハロゲン化炭化水素類等があげら
れ、特に芳香族炭化水素類およびエーテル類が
好適に使用される。また、使用されるアシル化
剤は、酸クロライド、酸ブロマイドのようなア
シルハライド;1,3−ジシクロヘキシルカル
ボジイミドのようなカルボジイミドの存在下に
おけるカルボン酸;または酸無水物、好適には
アシルクロライドであり、脱酸剤の存在下行な
われる。反応温度は特に限定はなく、室温乃至
溶剤の還流温度で行なわれる。反応時間は主に
反応温度、使用される試薬の種類によつて異な
るが約1乃至24時間である。
(4) 一般式()を有する化合物と金属との塩、
錯イオンとの塩およびアンモニウムイオンとの
塩は、式()の化合物をカチオンの存在下で
溶液のPHを約3以上に調整することにより形成
される。前記塩を形成させるための溶剤として
は特に限定はなくたとえば水;メタノール、エ
タノールのようなアルコール類;テトラヒドロ
フラン、ジオキサンのようなエーテル類;ベン
ゼンなどの芳香族炭化水素類;ジクロルメタ
ン、クロロホルムなどのハロゲン化炭化水素類
またはこれらの有機溶剤と水との混合溶剤が好
適に使用される。カチオンの原子価および溶剤
の変化に応じて、式()を有する化合物とカ
チオンが配位する割合は1:1,1:2,1:
3などと相異なる各種の塩が形成される。
なお、前記一般式()を有する化合物と金
属との塩は、特開昭52−265号または特開昭52
−266号明細書に記載の方法に準じて、対応す
るピラゾール誘導体の5−エステルを塩化アル
ミニウム、塩基性アルカリ金属塩または塩基性
アルカリ土類金属塩の存在下で反応させること
によつても得ることができる。
(5) 一般式()を有する化合物と鉱酸との塩
は、式()の化合物と鉱酸とを適当な溶剤中
で混和することにより容易に形成される。使用
される溶剤としては特に限定はなくたとえば
水;メタノール、エタノールのようなアルコー
ル類;テトラヒドロフラン、ジオキサンのよう
なエーテル類;ベンゼンなどの芳香族炭化水
素;ジクロルメタン、クロロホルムなどのハロ
ゲン化炭化水素類;アセトンのようなケトン類
またはこれらの有機溶剤と水との混合溶剤が好
適に使用される。一般に溶液のPHが約3以下に
おいて鉱酸との塩が形成される。
次に前記一般式()を有する化合物の製造法
を実施例によつて説明する。
実施例 1
1−(4−クロロフエニル)−3−メチル−4−
ベンゾイル−5−ヒドロキシピラゾール
1−(4−クロロフエニル)−3−メチル−5−
ピラゾロン1.043g、水酸化カルシウム0.74g、
ジオキサン3mlおよび塩化ベンゾイル0.705gの
混合物を撹拌しながら0.5時間加熱還流し、室温
に放冷後反応混合物を2N−塩酸溶液14.5mlを用
いて酸性となし、析出した結晶を取しメタノー
ルより再結晶して融点150.5〜152.5℃を有する目
的化合物0.994gを得た。(収率63.7%)
元素分析値(%)C17H13ClN2O2として
計算値 C,65.29;H,4.19;N,8.96;
Cl,11.33
実測値 C,65.03;H,4.12;N,8.99;
Cl,11.49
実施例 2
5−ヒドロキシ−1−メチル−3−フエニル−
4−(4−ニトロベンゾイル)ピラゾール
1−メチル−3−フエニル−5−ピラゾロン
0.87g、水酸化カルシウム0.74gおよびジオキサ
ン12mlの混合物を室温で撹拌しながら4−ニトロ
ベンゾイルクロリド0.93gをジオキサン3mlに溶
解した溶液を加え、1時間加熱還流し、放冷後反
応混合物に2N−塩酸溶液15mlおよび水50mlを加
え析出した結晶を取し、水で洗滌し乾燥して融
点159〜160℃(再結溶媒;エタノール)を有する
目的化合物1.0gを得た。収率62%
元素分析値(%)C17H13H3C4として
計算値 C,63.15;H,4.05;N,13.00
実測値 C,63.41;H,4.07;N,12.85
上記実施例1または2の方法に準じて次の化合
物が製造された。
1−(4−クロロフエニル)−3−メチル−4−
(2−クロロベンゾイル)−5−ヒドロキシピラゾ
ール、
m.p.138.5〜140℃
1−(4−クロロフエニル)−3−メチル−4−
(4−クロロベンゾイル)−5−ヒドロキシピラゾ
ール、
m.p.185〜186℃
1−フエニル−3−メチル−4−(4−クロロ
ベンゾイル)−5−ヒドロキシピラゾール、
m.p.150〜151℃
1−(フエニル−3−メチル−4−(2−メトキ
シベンゾイル)−5−ヒドロキシピラゾール、
νC=0;1600cm-1
1−(4−クロロフエニル)−3−メチル−4−
(4−ニトロベンゾイル)−5−ヒドロキシピラゾ
ール、
m.p.229〜230℃
1−(4−クロロフエニル)−3−メチル−4−
(2−メトキシベンゾイル)−5−ヒドロキシピラ
ゾール、
m.p.134〜135℃
1−(2−クロロフエニル)−3−メチル−4−
(2−クロロベンゾイル)−5−ヒドロキシピラゾ
ール、
m.p.132〜133℃
1−フエニル−3−メチル−4−o−トルオイ
ル−ヒドロキシピラゾール、
m.p.119〜120℃
1−フエニル−3−メチル−4−p−トルオイ
ル−5−ヒドロキシピラゾール、
m.p.101〜102℃
1−フエニル−3−メチル−4−(2,4−ジ
クロロベンゾイル)−5−ヒドロキシピラゾー
ル、
m.p.161〜162℃
1−フエニル−3−メチル−4−(3−メチル
−6−ニトロベンゾイル)−5−ヒドロキシピラ
ゾール、
m.p.240.5〜242℃
5−ヒドロキシ−1−メチル−3−フエニル−
4−(2−メトキシベンゾイル)ピラゾール、
m.p.102〜103℃
4−(2−クロロベンゾイル)−5−ヒドロキシ
−1−メチル−3−フエニルピラゾール、
m.p.142〜143℃
4−(4−クロロベンゾイル)−5−ヒドロキシ
−1−メチル−3−フエニルピラゾール、
m.p.100〜101.5℃
4−(3,5−ジメトキシベンゾイル)−5−ヒ
ドロキシ−1−メチル−3−フエニルピラゾー
ル、
m.p.128.5〜129.5℃
1−メチル−3−フエニル−4−ベンゾイル−
5−ヒドロキシピラゾール、
m.p.113〜114℃
4−(2,4−ジクロロベンゾイル)−5−ヒド
ロキシ−1−メチル−3−ピラゾリルアルデヒ
ド、
m.p.164〜165℃
1−メチル−3−フエニル−4−(2,4−ジ
クロロベンゾイル)−5−ヒドロキシピラゾー
ル、
m.p.114〜115℃
5−ヒドロキシ−4−(5−メチル−2−ニト
ロベンゾイル)−1−メチル−3−フエニルピラ
ゾール、
m.p.190〜191℃
実施例 3
1−フエニル−3−メチル−4−ベンゾイル−
5−ヒドロキシピラゾール アルミニウム塩
1−フエニル−3−メチル−5−ベンゾイルオ
キシピラゾール6gおよび塩化アルミニウム4.0
gを120〜130℃で加熱溶融し、冷後ジクロルエタ
ン30mlを加えて約1時間加熱撹拌する。放冷後、
反応混合物を水100ml中にあけ、ジクロルエタン
100mlを加えて撹拌した後、ジクロルエタン層を
分取し濃縮し、リグロインを加えて放置すると融
点265〜270℃を有する目的化合物6.0gを得た。
元素分析値(%)C17H13N2O2・Al/3として
計算値 C,71.32;H,4.58;N,9.78
実測値 C,70.41;H,4.47;N,9.68
上記実施例3の方法に準じて次の化合物が製造
された。
1−フエニル−3−メチル−4−o−トルオイ
ル−5−ヒドロキシピラゾール アルミニウム
塩、
m.p.125〜130℃
4−ベンゾイル−1−メチル−3−フエニル−
5−ヒドロキシピラゾール アルミニウム塩、
m.p.187〜189℃
実施例 4
5−アセトキシ−4−(2,4−クロロベンゾ
イル)3−メチル−1−フエニルピラゾール
1−フエニル−3−メチル−4−(2,4−ク
ロロベンゾイル)−5−ヒドロキシピラゾール
1.735gにベンゼン20mlおよびトリエチルアミン
0.51gを加え、室温で撹拌しながら塩化アセチル
0.4gを加えて更に室温で4時間撹拌した後、反
応混合物に水を加え析出した塩を除去し、ベンゼ
ン層を分取して5%炭酸水素ナトリウム水溶液、
水で順次洗滌し、無水硫酸ナトリウムで乾燥後、
減圧下に溶媒を留去すること目的化合物1.95gが
定量的に得られた。
融点89〜90℃(再結晶溶媒;n−ヘキサン)
元素分析値(%)C19H14Cl2O3として
計算値 C,58.63;H,3.62;N,7.19;
Cl,18.22
実測値 C,58.90;H,3.63;N,6.86;
Cl,18.41
上記実施例4の方法に準じて次の化合物が製造
された。
4−(2,4−ジクロロベンゾイル)−3−メチ
ル−1−フエニル−5−ピラゾリル p−トルエ
ンスルホネート、
前記一般式()の化合物、その塩およびその
有機酸エステルは除草剤として用いられ、雑草を
白化せしめ枯死に至らしめる特徴を有する。
水田においては、雑草の発芽前または発芽後に
土壌処理することにより、移植水稲および直播水
稲に対し害作用を及ぼすことなく、通常の除草剤
では防除が困難なホタルイ、ミズカヤツリ等のカ
ヤリツグサ科雑草、オモダカ、ウリカワ等のオモ
ダカ科雑草など多年生雑草を特に強力に駆除する
ことができ、さらに、タイヌビエ、イヌビエ、ハ
イヌメリ等のイネ科雑草など単子葉雑草、また、
アゼナ、ムラサキサギゴケ、アブノメ等のゴマノ
ハグサ科雑草、タネツケバナ、ミズタガラシ、ス
カシタゴボウ等のアブラナ科雑草、キカシグサ、
ミズマツバ等のミソハギ科雑草、オグルマ、タカ
サブロウ等のキク科雑草などの広葉雑草をも有効
に駆除することができる。
また、畑地においては、雑草の発芽前または発
芽後に土壌処理することにより、畑地の強雑草で
あるハコベ、ノミノフスマ、ミミナグサ、ツメク
サ等のナデシコ科雑草に特に有効であるほか、ス
ベリヒユ等のスベリヒユ科雑草、イヌビユ、アオ
ビユ等のヒユ科雑草、アカザ、シロザ、コアカザ
等のアカザ科雑草、ツユクサ等のツユクサ科雑
草、ホトケノザ、キランソウ等のシソ科雑草、カ
タバミ、ムラサキカタバミ等のカタバミ科雑草、
ネコハギ、スズメノエンドウ、カラスノエンドウ
等のマメ科雑草、エノキグサ、コニシキソウ等の
トウダイグサ科雑草などの広葉雑草を有効に駆除
することができる。
さらに、狭葉雑草では、ハマスゲ、カヤツリグ
サ等のカヤツリグサ科雑草に特に有効であるほ
か、カモジグサ、メヒシバ、コメヒシバ、イヌビ
エ、エノコログサ、アキノエノコログサ、スズメ
ノテツポウ等のイネ科雑草も有効に駆除すること
ができる。一方、実用薬量では稲、トウモロコ
シ、ビート、ダイズ、ワタ、ダイコン、トマト、
ニンジン、ハクサイ、レタス等の作物は薬害をう
けることはない。
さらに、前記一般式()を有する化合物は、
果樹園、非農耕地、山林等においても除草剤とし
て有効に使用することができる。
本発明の化合物は、担体および必要に応じて他
の補助剤と混合して、除草剤として通常用いられ
る製剤形態、たとえば、粉剤、粗粉剤、微粒剤、
粒剤、水和剤、乳剤、水溶液剤、水溶剤、油懸濁
剤等に調製されて使用される。ここでいう担体と
は、処理すべき部位へ有効成分化合物の到達性を
助け、また、有効成分化合物の貯蔵、輸送あるい
は取り扱いを容易にするために、除草剤中に混合
される合成または天然の無機または有機物質を意
味する。
適当な個体担体としては、カオリナイト群、モ
ンモリロナイト群あるいはアタバルジヤイト群等
で代表されるクレー類、タルク、雲母、葉ロウ
石、軽石、バーミユキライト、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、りん石灰、ゼオライト、無水ケイ酸、合成
ケイ酸カルシウム、等の無機物質、大豆粉、タバ
コ粉、クルミ粉、小麦粉、木粉、でんぷん、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、コーバルガム、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、密ロウ等の
ワックス類、あるいは尿素等があげられる。
適当な液体担体としては、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系も
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、0−クロルトルエン等の塩素化炭化水
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、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、シクロヘキサノール、ベン
ジルアルコール等のアルコール類、エチレングリ
コールエチルエーテル、ニ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
があげられる。
乳化、分散、湿潤、拡展、結合、崩壊性調節、
有効成分安定化、流動性改良、防錆等の目的で使
用される界面活性剤は、非イオン性、陰イオン
性、陽イオンおよび両性イオン性のいずれのもの
をも使用しうるが、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、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、オレイン酸等
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、ジラウリルりん酸等
の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
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等
があげられる。
さらに本発明の除草剤には製剤の性状を改善
し、生物効果を高める目的で、カゼイン、ゼラチ
ン、アルブミン、ニカワ、アルギン酸ソーダ、カ
ルボキシメチルセルロース、メチルセルロース、
ヒドロキシエチルセルロース、ポリビニルアルコ
ール等の高分子化合物や他の補助剤を併用するこ
ともできる。
上記の担体および種々の補助剤は製剤の剤型、
適用場面等を考慮して、目的に応じてそれぞれ単
独にあるいは組合せて適宜使用される。
粉剤は、例えば有効成分化合物を通常1ないし
25重量部含有し、残部は固体担体である。
水和剤は、例えば有効成分化合物を通常25ない
し90重量部含有し、残部は固体担体、分散湿潤剤
であつて、必要に応じて保護コロイド剤、チキソ
トロピー剤、消泡剤等が加えられる。
粒剤は、例えば有効成分化合物を通常1ないし
35重量部含有し、残部は大部分が固体担体であ
る。有効成分化合物は固体担体と均一に混合され
ているか、あるいは固体担体の表面に均一に固着
もしくは吸着されており、粒の径は約0.2ないし
1.5mm程度である。
乳剤は、例えば有効成分化合物を通常5ないし
50重量部含有しており、これに約5ないし20重量
部の乳化剤が含まれ、残部は液体担体であり、必
要に応じて防錆剤が加えられる。
このようにして種々の剤型に調製された本発明
の除草剤を、たとえば、水田または畑地において
雑草の発芽前または発芽後に土壌処理するとき
は、10aあたり有効成分として10ないし2000g好
ましくは100〜500gを投ずることにより、有効に
雑草を駆除することができる。また、非農耕地た
とえば、道路、グランド、家屋敷地、線路等にお
いて非選択的に雑草を駆除しようとするときは、
10aあたり有効成分として200ないし4000gを投ず
ることにより、有効に雑草を駆除できる。
本発明の除草剤は、殺草スペクトラムを広げる
ために他の除草剤が配合されることは好ましく、
場合によつては相乗効果を期待することもでき
る。このような他の除草剤の例としては、たとえ
ば、2−メチルチオ−4,6−ビスエチルアミノ
−1,3,5−トリアジン;2−クロル−4,6
−ビスエチルアミノ−1,3,5−トリアジン;
2−メトキシ−4−エチルアミノ−6−イソプロ
ピルアミノ−1,3,5−トリアジン;2−クロ
ル−4−エチルアミノ−6−イソプロピルアミノ
−S−トリアジン;2−メチルチオ−4,6−ビ
ス(イソプロピルアミノ)−S−トリアジン;2
−メチルチオ−4−エチルアミノ−6−イソプロ
ピルアミノ−S−トリアジン等のトリアジン系除
草剤、2,4−ジクロルフエノキシ酢酸およびそ
のメチル、エチルまたはブチルエステル;2−ク
ロル−4−メチルフエノキシ酢酸;4−クロル−
2−メチルフエノキシ酢酸、エチル2−メチル−
4−クロルフエノキシブチレート等のフエノキシ
系除草剤、2,4,6−トリクロルフエニル−
4′−ニトロフエニルエーテル、2,4−ジクロル
フエニル−4′−ニトロフエニルエーテル、2,4
−ジクロルフエニル−3′−メトキシ−4′−ニトロ
フエニルエーテル−;3,5−ジメチルフエニル
−4′−ニトロフエニルエーテル等のジフエニルエ
ーテル系除草剤、3−(3,4−ジクロルフエニ
ル)−1−メトキシ−1−メチルウレア;3−
(3,4−ジクロルフエニル)−1,1−ジメチル
ウレア;1−(α,α−ジメチルベンジル)−3−
(p−トリル)ウレア;3−(4−クロロフエニ
ル)−1,1−ジメチルウレア等の尿素系除草
剤、3−メトキシカルボニルアミノフエニル−N
−(3−メチルフエニル)カーバメート;イソピ
ロピル−N−(3−クロルフエニル)カーバメー
ト;メチルN−(3,4−ジクロロフエニル)カ
ーバメート等のカーバメート系除草剤、5−ブロ
ム−3−sec−ブチル−6−メチルウラシル;1
−シクロヘキシル−3,5−プロピレンウラシル
等のウラシル系除草剤、S−(4−クロルベンジ
ル)N,N−ジエチルチオールカーバメート;S
−エチルN−シクロヘキシル−N−エチルチオー
ルカーバメート;S−エチル−ヘキサヒドロ−
1H−アゼピン−1−カーボチオエート;S−エ
チル−N,N−ジノルマルプロピルチオカーバメ
ート等のチオールカーバメート系除草剤、1,
1′ジメチル−4,4′−ビスピリジニウムジクロラ
イド等のピリジニウム塩系除草剤、N−(ホスホ
ノメチル)グリシン等のリン系除草剤、α,α,
α−トリフルオロ−2,6−ジニトロ−N,N−
ジプロピル−p−トルイジン;4−(メチルスル
ホニル)2,6−ジニトロ−N,N−ジプロピル
アニリン等のアニリン系除草剤、2−クロル−
2′,6′ジエチル−N−(ブトキシメチル)アセト
アニリド、2−クロル−2′,6′−ジエチル−N−
(プロポキシエチル)アセトアニリド、2−クロ
ル−2′,6′−ジエチル−N−(メトキシメチル)
アセトアニリド;3,4−ジクロロプロピオンア
ニリド等の酸アニリド系除草剤、5−tert−ブチ
ル−3−(2,4−ジクロロ−5−イソプロポキ
シフエニル)1,3,4−オキサジアゾリン−2
−オン;2−〔N−イソプロピル、N−(4−クロ
ルフエニル)カルバモイル〕−4−クロル−5−
メチル−4−イソオキサゾリン−3−オン;3−
イソプロピル−ベンゾ−2−チア−1,3−ジア
ノゾン−(4)−2,2−ジオキシド;3−(2−メ
チルフエノキシ)ピリダジン等があげられるが、
これに限られるものではない。
本発明の除草剤はまた、ナフタリン酢酸ナトリ
ウム;1,2−ジヒドロピリダジン−3,6−ジ
オン;ジベレリン等の植物生長調節剤、メチル1
−(ブチルカルバモイル)−2−ベンズイミダゾー
ルカーバメート;1,2−ビス(3−メトキシカ
ルボニル−2−チオウレイド)ベンゼン;3−ヒ
ドロキシ−5−メチルイソキサゾール;N−2,
3−ジクロルフエニルテトラクロルフタルアミド
酸;5−メチルS−トリアゾール(3,4−b)
ベンズチアゾール;0,0−ジイソプロピル−S
−ベンジルホスホロチオエート;ペンタクロロニ
トロベンゼン;カスガマイシン;ブラストサイジ
ンS;4,5,6,7−テトラクロロフタリド等
の殺菌剤、0,0−ジエチル0−(2−イソプロ
ピル−4−メチル−6−ピリミジニル)ホスホロ
チオエート;0,0−ジエチルS−2−〔(エチル
チオ)エチル〕ホスホロジチオエート;1−ナフ
チルN−メチルカーバメート;0,0−ジメチル
0−(3−メチル−4−ニトロフエニル)チオホ
スフエート;0,0−ジメチルS−(N−メチル
カーバモイルメチル)ホスホロジチオエート;S
−メチル−N−〔(メチルカーバモイル)オキシ〕
チオアセトイミデート;0,0−ジメチルS−
(N−メチル−N−ホルミルカ−バモイルメチ
ル)ホスホロジチオエート;0,0−ジメチルS
−2−(エチルチオ)エチルホスホロジチオエー
ト;0,0−ジエチルS−2〔(エチルチオ)エ
チル〕ホスホロジチオエート;0,0−ジメチル
−1−ヒドロキシ−2,2,2−トリクロロエチ
ルホスホネート等の殺虫剤あるいは肥料等を混合
して使用することができる。
本発明の除草剤の製剤例を次にあげる。文中、
単に部とあるのは全て重量部を意味する。
製剤例 1
粒 剤
化合物番号2の化合物70部を微細に粉砕し、こ
れにクレー30部を加えて混合機中で混和してプレ
ミツクスとする。このプレミツクス10部をクレー
60部およびベントナイト30部と共に混合機中で均
一に混和する。このものに適当量の水を加え、ニ
ーダー中で捏和し、直径0.8mmのスクリーンより
押し出し、50℃の通風乾燥機中で乾燥する。この
ものをシフターによつて整粒して粒剤を得る。
製剤例 2
粒 剤
化合物番号4の化合物35部およびS−(4−ク
ロロベンジル)N,N−ジエチルチオールカーバ
メート35部を微細に粉砕し、これにホワイトカー
ボン30部を加えて混合機中で混和してプレミツク
スを得る。このプレミツクス20部をクレー50部お
よびベントナイト30部と共に混合機中で均一に混
和する。このものに適当量の水を加え、ニーダー
中で捏和し、直径0.8mmのスクリーンより押し出
し、50℃の通風乾燥機中で乾燥する。このものを
シフターによつて整粒して混合粒剤を得る。
製剤例 3
水和剤
化合物番号17の化合物50部、クレー29部、硅藻
土10部、ホワイトカーボン5部、リグニンスルホ
ン酸ナトリウム3部、ニユーコール1106(日本乳
化剤社商品名)2部およびポリビニルアルコール
1部を混合機中で均一に混合し、ハンマーミルで
3回粉砕して水和剤を得る。
製剤例 4
乳 剤
化合物番号34の化合物20部、キシレン65部およ
びパコラールps(日本乳化剤社商品名)15部を
混合し、均一に溶解させて乳剤を得る。
このようにして調製された本発明の除草剤の試
験例を次にあげる。なお、供試薬剤は前記製剤例
3に準じて製造し、本発明の有効成分化合物を50
%含有する水和剤を用いた。
試験例 1
水田雑草湛水土壌処理試験
表面積45cm2のポリエチレン製ポツト3ケ(A,
B,Cと略称する)に水田土壌を充填し、ポツト
Aに水稲(品種:金南風)2.5葉期の苗を1株
(2本)移植し、多年生雑草の代表としてウリカ
ワの塊茎を2ケ植え込む。ポツトBに広葉雑草の
代表としてコナギ、アゼナおよびアブノメの各種
子を土とよく混和する。さらにマツバイの生育株
を1株移植し、多年生雑草のミズカヤツリの塊茎
をポツトあたり2ケを植え込む。ポツトCには狭
葉雑草の代表として、タイヌビエおよびホタルイ
の各種子を土とよく混和する。さらに多年生雑草
のオモダカの塊茎をポツトあたり2ケ植え込む。
ポツトA,BおよびCとも水田状態として3日間
温室内で栽培し、植物の活養後供試薬剤の懸濁液
をポツトあたり10c.c.ずつ湛水状態で土壌処理し
た。処理20日後に各雑草に対する除草効果および
水稲に対する薬害を観察判定した。その結果を第
1表に示す。ただし、表中におる有効薬量(g/
a)は、各植物の生育阻害程度(植物体表面の白
化面積)ぱ70%以上となる最低薬量を示す。
The present invention is based on the general formula (In the formula, when R 1 represents a lower alkyl group, R 2
represents a phenyl group or a halogen-substituted phenyl group, and when R 1 represents a phenyl group or a formyl group, R 2 represents a lower alkyl group. X represents a lower alkyl group, lower alkoxy group, nitro group or halogen atom, n represents 0, 1 or 2, and when n is 2, X may be the same or different from each other. ), a salt thereof, or an aliphatic or aromatic carboxylic acid or sulfonic acid ester thereof as an active ingredient. The compound of the general formula () can exist as a tautomer as shown below. (In the formula, R 1 , R 2 , It represents a straight or branched lower alkyl group having 1 to 4 carbon atoms such as butyl or isobutyl. X is preferably a linear or branched lower alkyl group having 1 to 4 carbon atoms as exemplified above; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isoptoxy A linear or branched lower alkoxy group having 1 to 4 carbon atoms; a nitro group; a halogen atom such as chlorine, bromine, fluorine or iodine. Examples of the salt of the compound of the general formula () include salts with monovalent to trivalent metal ions such as sodium, potassium, calcium, magnesium, aluminum, iron, manganese, zinc, nickel, cobalt, or copper; Cu(H 2 O) 2 ] ++ , [Mn
(H 2 O) 2 ] ++ , [Ni(H 2 O) 4 ] ++ , [Al(OH)] ++ ,
Salts with complex ions such as [Zn(OH)] + , [Cu(OH)] + , [Cu(NH 3 ) 2 ] ++ or [Co(NH 2 CH 2 CH 2 NH 2 )] ++ ;N + H 4 , N + H(CH 3 ) 3 , N + H 2
(C 2 H 5 ) 2 , N + H 3 CH (CH 3 ) 2 , N + H 3 CH 2 CH 2 OH
or salts with ammonium ions such as N + H 3 CH 3 CH 2 CH 2 OC 2 H 5 ; salts with mineral acids such as hydrochloric, sulfuric, nitric or hydrobromic acids. The organic acid ester of the compound of the general formula () may be an ester with an organic acid that is formed at the 5-position of the pyrazole ring and produces the compound of the general formula () upon decomposition. Such organic acids include (1) fatty acids or aromatic carboxylic acids, such as those of the formula R 3 COOH, where R 3 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl; a straight-chain or branched alkyl group having 1 to 4 carbon atoms; or phenyl, 2- or 4-nitrophenyl, 2-, 3- or 4-tolyl, 2- or 4-chlorophenyl, 2- Or 4-
Bromophenyl, 2,4-dichlorophenyl,
Having 1 to 3 nitro, halogen, and/or alkyl groups having 1 to 4, especially 1, carbon atoms as substituents, such as 2,4,6-trichlorophenyl or 2-chloro-4-nitrophenyl Indicates a phenyl group with or without. (2) Sulfonic acid, for example, formula R 4 -SO 2 -OH where R 4 is a straight chain having 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl or isobutyl. or a branched lower alkyl group; or methyl, ethyl, n-propyl, isopropyl, n
- A phenyl group with or without a linear or branched alkyl having 1 to 4 carbon atoms, especially 1 or 2 carbon atoms, such as butyl or isobutyl, or a halogen such as chloro, as a substituent. Examples of compounds having the general formula () used in the herbicide of the present invention are as follows (compound numbers are referred to in the following description) Compound number Compound 1 1-Phenyl- 3-Methyl-4-benzoyl-5-hydroxypyrazole 2 1-(4-chlorophenyl)-3-methyl-
4-benzoyl-5-hydroxypyrazole 3 1-(4-chlorophenyl)-3-methyl-4
-(2-chlorobenzoyl)-5-hydroxypyrazole 4 1-(4-chlorophenyl)-3-methyl-4
-(4-chlorobenzoyl)-5-hydroxypyrazole 5 1-phenyl-3-methyl-4-(2-chlorobenzoyl)-5-hydroxypyrazole 6 1-phenyl-3-methyl-4-(4-chlorobenzoyl )-5-hydroxypyrazole 7 1-phenyl-3-methyl-4-(2-methoxybenzoyl)-5-hydroxypyrazole 8 1-phenyl-3-methyl-4-(4-nitrobenzoyl)-5-hydroxypyrazole 9 1-(4-chlorophenyl)-3-methyl-4
-(4-nitrobenzoyl)-5-hydroxypyrazole 10 1-(4-chlorophenyl)-3-methyl-4
-(2-methoxybenzoyl)-5-hydroxypyrazole 11 1-(2-chlorophenyl)-3-methyl-4
-(2-chlorobenzoyl)-5-hydroxypyrazole 12 1-phenyl-3-methyl-4-benzoyl-5-hydroxypyrazole Aluminum salt 13 1-phenyl-3-methyl-4-o-toluoyl-5-hydroxypyrazole Aluminum salt 14 1-phenyl-3-methyl-4-o-toluoyl-5-hydroxypyrazole 15 1-phenyl-3-methyl-4-p-toluoyl-5-hydroxypyrazole 17 1-phenyl-3-methyl-4 -(2,4-
dichlorobenzoyl)-5-hydroxypyrazole 18 5-acetoxy-4-(2,4-dichlorobenzoyl)-3-methyl-1-phenylpyrazole 19 4-(2,4-dichlorobenzoyl)-3-methyl-1 Phenyl-5-pyrazolyl p-toluenesulfonate 20 1-phenyl-3-methyl-4-(3-methyl-6-nitrobenzoyl)-5-hydroxypyrazole 21 5-hydroxy-1-methyl-3-phenyl-4- (4-nitrobenzoyl)pyrazole22 5-hydroxy-1-methyl-3-phenyl-4-(2-methoxybenzoyl)pyrazole23 4-(2-chlorobenzoyl)-5-hydroxy-1-methyl-3-phenyl Enylpyrazole24 4-(4-chlorobenzoyl)-5-hydroxy-1-methyl-3-phenylpyrazole25 4-(3,5-dimethoxybenzoyl)-5-hydroxy-1-methyl-3-phenyl Pyrazole 29 4-benzoyl-1-methyl-3-phenyl-5-hydroxypyrazole aluminum salt 30 1-methyl-3-phenyl-4-benzoyl-5-hydroxypyrazole 34 4-(2,4-dichlorobenzoyl)-5 -Hydroxy-1-methyl-3-pyrazolylaldehyde35 1-methyl-3-phenyl-4-(2,4-
dichlorobenzoyl)-5-hydroxypyrazole36 5-hydroxy-4-(5-methyl-2-nitrobenzoyl)-1-methyl-3-phenylpyrazole The above compounds are represented by compound numbers 1, 5, 8. Except for the compound, all of them are new compounds that have not been published in literature, and the compound having the general formula (), its salt, and its organic acid ester are produced by the following method. (1) A compound having the general formula () is easily produced by reacting a 5-pyrazolone derivative () with an acyl halide () in the presence of a catalyst, as shown in the following formula. (In the formula, R 1 , R 2 , X and n are the same as those described above.) The above reaction is suitably carried out in the presence of a solvent. The solvent used is not particularly limited as long as it does not participate in this reaction, and examples include diethyl ether, tetrahydrofuran, and diethyl ether.
Ethers or mixed solvents thereof such as dioxane, tetrahydrofuran-dioxane; halogenated hydrocarbons such as dichloromethane and carbon tetrachloride; secondary or tertiary alcohols such as isopropanol, isobutanol, tert-butanol, etc. In particular, ethers and secondary alcohols are preferably used. The reaction is also suitably carried out in the presence of a catalyst. Examples of the catalyst used include alkaline earth metal hydroxides such as calcium hydroxide, metal chlorides such as aluminum chloride, and particularly calcium hydroxide is preferably used. The amount of catalyst to be used is preferably 1 to 2 mol per 1 mol of the starting compound of formula (). The reaction temperature is not particularly limited and is carried out at room temperature to the reflux temperature of the solvent, particularly preferably near the reflux temperature of the solvent. The reaction time varies mainly depending on the reaction temperature and the type of reagent used, but is about 1 to 10 hours. Furthermore, the acyl halide used in the above reaction is, for example, acid chloride or acid bromide. After the reaction is completed, the target compound is collected from the reaction mixture according to a conventional method. The starting compound of formula () is produced according to the method described in Berichte (Ber.) 43, 2106 (1910). (2) A compound having the general formula () can be prepared by heating the corresponding 5-halogenovirazole derivative () with an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, as shown in the following formula. You can get it even if you twist it. (In the formula, R 1 , R 2 , X and n have the same meanings as described above.) In the above reaction, water can be used as a solvent. Further, a mixed solvent of water and an organic solvent can also be used, and examples of such organic solvents include ethers such as tetrahydrofuran and dioxane; and alcohols such as methanol and ethanol. The reaction temperature is not particularly limited, and is carried out at room temperature to the reflux temperature of the solvent, particularly preferably near the reflux temperature of the solvent. The reaction time varies mainly depending on the reaction temperature and the type of reagent used, but is about 1 to 10 hours. The raw material compound of formula () is based on Berichte (Ber.) 50, 737 (1917) and British Patent No.
Manufactured according to the method described in No. 1268608. (3) It is easily produced by reacting an organic acid ester () of a compound having the general formula () or a compound of the formula () as shown in the following formula with an acylating agent. (In the formula, R 1 , R 2 , X and n have the same meanings as defined above, and R 5 represents an organic acid residue.) The above reaction is preferably carried out in the presence of a solvent. The solvent used is not particularly limited as long as it does not participate in this reaction, and examples include diethyl ether, tetrahydrofuran, and diethyl ether.
Ethers such as dioxane, tetrahydrofuran-dioxane, or mixed solvents thereof; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; Hydrocarbons and ethers are preferably used. The acylating agent used can also be an acyl halide, such as an acid chloride, an acid bromide; a carboxylic acid in the presence of a carbodiimide, such as 1,3-dicyclohexylcarbodiimide; or an acid anhydride, preferably an acyl chloride. , carried out in the presence of a deoxidizing agent. The reaction temperature is not particularly limited, and is carried out at room temperature to the reflux temperature of the solvent. The reaction time varies mainly depending on the reaction temperature and the type of reagent used, but is about 1 to 24 hours. (4) a salt of a compound having the general formula () and a metal;
Salts with complex ions and salts with ammonium ions are formed by adjusting the pH of the solution of the compound of formula () to about 3 or higher in the presence of a cation. The solvent for forming the salt is not particularly limited, and includes, for example, water; alcohols such as methanol and ethanol; ethers such as tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene; and halogens such as dichloromethane and chloroform. Hydrocarbons or a mixed solvent of these organic solvents and water are preferably used. Depending on the valence of the cation and the solvent, the coordination ratio of the compound having the formula () and the cation is 1:1, 1:2, 1:
Various types of salts, such as 3, are formed. In addition, the salt of the compound having the general formula () with a metal is disclosed in JP-A No. 52-265 or JP-A-52
It can also be obtained by reacting the 5-ester of the corresponding pyrazole derivative in the presence of aluminum chloride, a basic alkali metal salt or a basic alkaline earth metal salt, according to the method described in No. 266. be able to. (5) A salt of a compound having general formula () and a mineral acid can be easily formed by mixing the compound of formula () and a mineral acid in an appropriate solvent. The solvent used is not particularly limited, and includes, for example, water; alcohols such as methanol and ethanol; ethers such as tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene; halogenated hydrocarbons such as dichloromethane and chloroform; Ketones such as acetone or a mixed solvent of these organic solvents and water are preferably used. Generally, salts with mineral acids are formed when the pH of the solution is about 3 or less. Next, a method for producing a compound having the above general formula () will be explained with reference to Examples. Example 1 1-(4-chlorophenyl)-3-methyl-4-
Benzoyl-5-hydroxypyrazole 1-(4-chlorophenyl)-3-methyl-5-
Pyrazolone 1.043g, calcium hydroxide 0.74g,
A mixture of 3 ml of dioxane and 0.705 g of benzoyl chloride was heated to reflux for 0.5 hour with stirring, and after cooling to room temperature, the reaction mixture was made acidic using 14.5 ml of 2N hydrochloric acid solution, and the precipitated crystals were collected and recrystallized from methanol. 0.994 g of the target compound having a melting point of 150.5-152.5°C was obtained. (Yield 63.7%) Elemental analysis value (%) Calculated value as C 17 H 13 ClN 2 O 2 C, 65.29; H, 4.19; N, 8.96;
Cl, 11.33 Actual value C, 65.03; H, 4.12; N, 8.99;
Cl, 11.49 Example 2 5-hydroxy-1-methyl-3-phenyl-
4-(4-nitrobenzoyl)pyrazole 1-methyl-3-phenyl-5-pyrazolone
A solution of 0.93 g of 4-nitrobenzoyl chloride dissolved in 3 ml of dioxane was added to a mixture of 0.87 g of calcium hydroxide, 0.74 g of calcium hydroxide, and 12 ml of dioxane with stirring at room temperature, heated under reflux for 1 hour, and after cooling, the reaction mixture was diluted with 2N- 15 ml of hydrochloric acid solution and 50 ml of water were added, and the precipitated crystals were collected, washed with water and dried to obtain 1.0 g of the target compound having a melting point of 159-160°C (recrystallization solvent: ethanol). Yield 62% Elemental analysis value (%) C 17 H 13 H 3 C 4 Calculated value C, 63.15; H, 4.05; N, 13.00 Actual value C, 63.41; H, 4.07; N, 12.85 Above Example 1 or The following compound was produced according to method 2. 1-(4-chlorophenyl)-3-methyl-4-
(2-chlorobenzoyl)-5-hydroxypyrazole, mp138.5-140℃ 1-(4-chlorophenyl)-3-methyl-4-
(4-chlorobenzoyl)-5-hydroxypyrazole, mp185-186℃ 1-phenyl-3-methyl-4-(4-chlorobenzoyl)-5-hydroxypyrazole, mp150-151℃ 1-(phenyl-3-methyl -4-(2-methoxybenzoyl)-5-hydroxypyrazole, ν C=0 ; 1600cm -1 1-(4-chlorophenyl)-3-methyl-4-
(4-Nitrobenzoyl)-5-hydroxypyrazole, mp229-230℃ 1-(4-chlorophenyl)-3-methyl-4-
(2-methoxybenzoyl)-5-hydroxypyrazole, mp134-135℃ 1-(2-chlorophenyl)-3-methyl-4-
(2-chlorobenzoyl)-5-hydroxypyrazole, mp132-133°C 1-phenyl-3-methyl-4-o-toluoyl-hydroxypyrazole, mp119-120°C 1-phenyl-3-methyl-4-p-toluoyl -5-hydroxypyrazole, mp101~102℃ 1-phenyl-3-methyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole, mp161~162℃ 1-phenyl-3-methyl-4-(3 -Methyl-6-nitrobenzoyl)-5-hydroxypyrazole, mp240.5-242℃ 5-hydroxy-1-methyl-3-phenyl-
4-(2-methoxybenzoyl)pyrazole, mp102-103℃ 4-(2-chlorobenzoyl)-5-hydroxy-1-methyl-3-phenylpyrazole, mp142-143℃ 4-(4-chlorobenzoyl)- 5-Hydroxy-1-methyl-3-phenylpyrazole, mp100-101.5℃ 4-(3,5-dimethoxybenzoyl)-5-hydroxy-1-methyl-3-phenylpyrazole, mp128.5-129.5℃ 1 -Methyl-3-phenyl-4-benzoyl-
5-hydroxypyrazole, mp113-114℃ 4-(2,4-dichlorobenzoyl)-5-hydroxy-1-methyl-3-pyrazolyl aldehyde, mp164-165℃ 1-methyl-3-phenyl-4-(2, 4-Dichlorobenzoyl)-5-hydroxypyrazole, mp114-115°C 5-hydroxy-4-(5-methyl-2-nitrobenzoyl)-1-methyl-3-phenylpyrazole, mp190-191°C Example 3 1 -Phenyl-3-methyl-4-benzoyl-
5-hydroxypyrazole aluminum salt 1-phenyl-3-methyl-5-benzoyloxypyrazole 6g and aluminum chloride 4.0
After cooling, 30 ml of dichloroethane is added and the mixture is heated and stirred for about 1 hour. After cooling,
Pour the reaction mixture into 100ml of water and add dichloroethane.
After adding 100 ml and stirring, the dichloroethane layer was separated and concentrated, and ligroin was added and left to stand to obtain 6.0 g of the target compound having a melting point of 265-270°C. Elemental analysis value (%) C 17 H 13 N 2 O 2・Al/ As 3 Calculated value C, 71.32; H, 4.58; N, 9.78 Actual value C, 70.41; H, 4.47; N, 9.68 The following compounds were produced according to the method. 1-phenyl-3-methyl-4-o-toluoyl-5-hydroxypyrazole aluminum salt, mp125-130℃ 4-benzoyl-1-methyl-3-phenyl-
5-hydroxypyrazole aluminum salt, mp187-189℃ Example 4 5-acetoxy-4-(2,4-chlorobenzoyl)3-methyl-1-phenylpyrazole 1-phenyl-3-methyl-4-(2, 4-chlorobenzoyl)-5-hydroxypyrazole
1.735g with 20ml of benzene and triethylamine
Add 0.51g of acetyl chloride while stirring at room temperature.
After adding 0.4 g and further stirring at room temperature for 4 hours, water was added to the reaction mixture to remove the precipitated salt, and the benzene layer was separated, and 5% aqueous sodium hydrogen carbonate solution,
After sequentially washing with water and drying with anhydrous sodium sulfate,
By distilling off the solvent under reduced pressure, 1.95 g of the target compound was quantitatively obtained. Melting point 89-90℃ (recrystallization solvent: n-hexane) Elemental analysis value (%) Calculated value as C 19 H 14 Cl 2 O 3 C, 58.63; H, 3.62; N, 7.19;
Cl, 18.22 Actual value C, 58.90; H, 3.63; N, 6.86;
Cl, 18.41 The following compound was prepared according to the method of Example 4 above. 4-(2,4-dichlorobenzoyl)-3-methyl-1-phenyl-5-pyrazolyl p-toluenesulfonate, the compound of the general formula (), its salts, and its organic acid esters are used as herbicides and are used to control weeds. It has the characteristic of causing whitening and death. In paddy fields, by treating the soil before or after the germination of weeds, it is possible to eliminate harmful effects on transplanted rice and direct-seeded rice. It can particularly powerfully exterminate perennial weeds such as Omodacaceae weeds such as Prunus japonicus, and monocotyledonous weeds such as Poaceae weeds such as Japanese grasshopper, Japanese grasshopper, and Poaceae weeds.
Weeds of the Weedaceae family, such as azeena, Japanese aphrodisiac moss, and Abnome;
It is also possible to effectively exterminate broad-leaved weeds such as weeds of the Lythraceae family, such as Physcomitrella japonica, and weeds of the Asteraceae family, such as Asteraceae and Asteraceae. In addition, in fields, by treating the soil before or after the germination of weeds, it is particularly effective against weeds of the Caryophyllaceae family, such as chickweed, flea weed, Japanese clover, and clover, as well as weeds of the Caryophyllaceae family, such as Purslane. , weeds of the Amaranthaceae family, such as oxalis, and oxalis; weeds of the Chenopodiaceae family, such as pigweed, white daisy, and koakaza; weeds of the genus Cypressaceae, such as dayflower; weeds of the Lamiaceae family, such as Oxalis oxalis and Oxalis oxalis;
It is possible to effectively exterminate broad-leaved weeds such as leguminous weeds such as catfish, sycamore, and crow pea, and weeds of the euphorbiaceae family such as hackberry and cornucopia. Furthermore, among narrow-leaved weeds, it is particularly effective against weeds of the Cyperaceae family, such as Cyperus japonica and Cyperus japonica, as well as weeds of the Poaceae family, such as Cyperus japonica, Cyperus japonica, Rice grass weed, Golden millet, hackberry grass, Golden foxtail grass, and Sparrow grass. On the other hand, in practical doses, rice, corn, beets, soybeans, cotton, radish, tomatoes,
Crops such as carrots, Chinese cabbage, and lettuce are not harmed by the plant. Furthermore, the compound having the general formula () is
It can also be effectively used as a herbicide in orchards, non-agricultural lands, forests, etc. The compound of the present invention can be mixed with a carrier and, if necessary, other adjuvants, to form a formulation commonly used as a herbicide, such as powder, coarse powder, fine granules, etc.
It is prepared and used as granules, wettable powders, emulsions, aqueous solutions, aqueous solutions, oil suspensions, etc. The carrier here refers to a synthetic or natural carrier that is mixed into the herbicide to aid in the reach of the active ingredient to the area to be treated, and to facilitate the storage, transportation, or handling of the active ingredient. means an inorganic or organic substance. Suitable solid carriers include clays represented by kaolinite group, montmorillonite group, or attabulgite group, talc, mica, phyllite, pumice, vermiyquilite, gypsum, calcium carbonate, dolomite, diatomaceous earth, and magnesium. Inorganic substances such as lime, phosphoric lime, zeolite, anhydrous silicic acid, synthetic calcium silicate, vegetable organic substances such as soybean powder, tobacco powder, walnut powder, wheat flour, wood flour, starch, crystalline cellulose, coumaron resin,
Examples include synthetic or natural polymeric compounds such as petroleum resins, alkyd resins, polyvinyl chloride, polyalkylene glycols, ketone resins, ester gums, cobal gums, and dammar gums, waxes such as carnauba wax and beeswax, and urea. Suitable liquid carriers include paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, white oil, aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, methylnaphthalene, carbon tetrachloride, chloroform, etc. , chlorinated hydrocarbons such as trichloroethylene, monochlorobenzene, 0-chlorotoluene, ethers such as dioxane and 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, dibutyl maleate, diethyl succinate, alcohols such as methanol, n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, benzyl alcohol, ethylene glycol ethyl ether, nitylene glycol phenyl ether , ether alcohols such as diethylene glycol ethyl ether and diethylene glycol butyl ether, dimethylformamide,
Examples include polar solvents such as dimethyl sulfoxide, water, and the like. Emulsification, dispersion, wetting, spreading, binding, disintegration control,
Surfactants used for the purpose of stabilizing active ingredients, improving fluidity, preventing rust, etc. can be nonionic, anionic, cationic, or amphoteric, but usually Non-ionic and/or anionic ones are 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 alkylnaphthols such as butylnaphthol and octylnaphthol, products obtained by polymerizing and adding ethylene oxide to higher fatty acids such as palmitic acid, stearic acid, and oleic acid, stearyl phosphoric acid, dilauryl phosphoric acid, etc. mono- or dialkyl phosphoric acid with ethylene oxide polymerized and added, amines such as dodecylamine and stearic acid amide with ethylene oxide polymerized and added, higher fatty acid esters of polyhydric alcohols such as sorbitan, and ethylene oxide polymerized and added to them. Examples include those obtained by polymerizing and adding ethylene oxide and propylene oxide. Suitable anionic surfactants include, for example, sodium lauryl sulfate, alkyl sulfate salts such as oleyl alcohol sulfate amine salts, alkyl sulfonates 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. Furthermore, the herbicide of the present invention includes casein, gelatin, albumin, glue, sodium alginate, carboxymethyl cellulose, methyl cellulose,
High molecular compounds such as hydroxyethyl cellulose and polyvinyl alcohol and other auxiliary agents can also be used in combination. The above-mentioned carriers and various adjuvants are used in the dosage form of the preparation,
They are used individually or in combination as appropriate depending on the purpose, taking into consideration the application situation. Powders, for example, usually contain 1 to 10% of the active ingredient compound.
It contains 25 parts by weight, and the remainder is solid carrier. Wettable powders usually contain, for example, 25 to 90 parts by weight of the active ingredient compound, with the remainder being a solid carrier and a dispersing wetting agent, with protective colloid agents, thixotropic agents, antifoaming agents, etc. being added as necessary. Granules, for example, usually contain 1 to 1 active ingredient compound.
It contains 35 parts by weight, and the remainder is mostly solid carrier. The active ingredient compound is uniformly mixed with the solid carrier, or is uniformly fixed or adsorbed on the surface of the solid carrier, and the particle size is about 0.2 to
It is about 1.5mm. Emulsions, for example, usually contain 5 to 5 active ingredients.
This includes approximately 5 to 20 parts by weight of an emulsifier, and the remainder is a liquid carrier, with a rust preventive added as needed. When the herbicide of the present invention prepared in various dosage forms in this way is used to treat soil before or after the germination of weeds in rice fields or fields, the amount of active ingredient per 10 acres is preferably 10 to 2000 g, preferably 100 to 2000 g. Weeds can be effectively exterminated by throwing 500g. In addition, when trying to non-selectively exterminate weeds in non-agricultural lands, such as roads, grounds, house grounds, railroad tracks, etc.,
Weeds can be effectively exterminated by applying 200 to 4000g of the active ingredient per 10 acres. The herbicide of the present invention is preferably blended with other herbicides in order to broaden the herbicidal spectrum.
In some cases, synergistic effects can be expected. Examples of such other herbicides include, for example, 2-methylthio-4,6-bisethylamino-1,3,5-triazine; 2-chloro-4,6
-bisethylamino-1,3,5-triazine;
2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine; 2-chloro-4-ethylamino-6-isopropylamino-S-triazine; 2-methylthio-4,6-bis( isopropylamino)-S-triazine; 2
- Triazine herbicides such as methylthio-4-ethylamino-6-isopropylamino-S-triazine, 2,4-dichlorophenoxyacetic acid and its methyl, ethyl or butyl ester; 2-chloro-4-methylphenoxyacetic acid; 4-chlor-
2-methylphenoxyacetic acid, ethyl 2-methyl-
Phenoxy herbicides such as 4-chlorophenoxybutyrate, 2,4,6-trichlorophenyl-
4'-nitrophenyl ether, 2,4-dichlorophenyl-4'-nitrophenyl ether, 2,4
-Dichlorophenyl-3'-methoxy-4'-nitrophenyl ether-; Diphenyl ether herbicides such as 3,5-dimethylphenyl-4'-nitrophenyl ether, 3-(3,4-dichlorophenyl) -1-methoxy-1-methylurea; 3-
(3,4-dichlorophenyl)-1,1-dimethylurea; 1-(α,α-dimethylbenzyl)-3-
(p-tolyl)urea; urea-based herbicides such as 3-(4-chlorophenyl)-1,1-dimethylurea, 3-methoxycarbonylaminophenyl-N
-(3-methylphenyl)carbamate; Isopropyl-N-(3-chlorophenyl)carbamate; Carbamate herbicides such as methyl N-(3,4-dichlorophenyl)carbamate, 5-bromo-3-sec-butyl-6 -Methyluracil; 1
- Uracil herbicides such as cyclohexyl-3,5-propylene uracil, S-(4-chlorobenzyl) N,N-diethylthiol carbamate; S
-ethyl N-cyclohexyl-N-ethylthiol carbamate; S-ethyl-hexahydro-
1H-Azepine-1-carbothioate; Thiol carbamate herbicides such as S-ethyl-N,N-dinorpropylthiocarbamate, 1,
Pyridinium salt herbicides such as 1'dimethyl-4,4'-bispyridinium dichloride, phosphorus herbicides such as N-(phosphonomethyl)glycine, α, α,
α-Trifluoro-2,6-dinitro-N,N-
Dipropyl-p-toluidine; aniline herbicides such as 4-(methylsulfonyl)2,6-dinitro-N,N-dipropylaniline, 2-chloro-
2',6'diethyl-N-(butoxymethyl)acetanilide, 2-chloro-2',6'-diethyl-N-
(Propoxyethyl)acetanilide, 2-chloro-2',6'-diethyl-N-(methoxymethyl)
Acetanilide; acid anilide herbicides such as 3,4-dichloropropionanilide, 5-tert-butyl-3-(2,4-dichloro-5-isopropoxyphenyl) 1,3,4-oxadiazoline-2
-one; 2-[N-isopropyl, N-(4-chlorophenyl)carbamoyl]-4-chloro-5-
Methyl-4-isoxazolin-3-one; 3-
Examples include isopropyl-benzo-2-thia-1,3-dianozone-(4)-2,2-dioxide; 3-(2-methylphenoxy)pyridazine, etc.
It is not limited to this. The herbicides of the present invention may also be used as plant growth regulators such as sodium naphthalene acetate; 1,2-dihydropyridazine-3,6-dione; gibberellin;
-(Butylcarbamoyl)-2-benzimidazole carbamate; 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene; 3-hydroxy-5-methylisoxazole; N-2,
3-Dichlorophenyltetrachlorophthalamic acid; 5-methyl S-triazole (3,4-b)
Benzthiazole; 0,0-diisopropyl-S
-benzyl phosphorothioate; pentachloronitrobenzene; kasugamycin; blasticidin S; fungicides such as 4,5,6,7-tetrachlorophthalide, 0,0-diethyl 0-(2-isopropyl-4-methyl-6- pyrimidinyl) phosphorothioate; 0,0-diethyl S-2-[(ethylthio)ethyl] phosphorodithioate; 1-naphthyl N-methyl carbamate; 0,0-dimethyl 0-(3-methyl-4-nitrophenyl) thiophosphate; 0,0-dimethyl S-(N-methylcarbamoylmethyl)phosphorodithioate; S
-Methyl-N-[(methylcarbamoyl)oxy]
Thioacetimidate; 0,0-dimethyl S-
(N-methyl-N-formylcarbamoylmethyl)phosphorodithioate; 0,0-dimethyl S
-2-(ethylthio)ethylphosphorodithioate; 0,0-diethyl S-2[(ethylthio)ethyl]phosphorodithioate; 0,0-dimethyl-1-hydroxy-2,2,2-trichloroethylphosphonate It can be used in combination with other pesticides or fertilizers. Examples of formulations of the herbicide of the present invention are given below. In the text,
All parts simply refer to parts by weight. Formulation Example 1 Granules Finely grind 70 parts of Compound No. 2, add 30 parts of clay, and mix in a mixer to obtain a premix. Clay 10 parts of this premix.
Mix homogeneously in a mixer with 60 parts and 30 parts of bentonite. Add an appropriate amount of water to this mixture, knead it in a kneader, extrude it through a screen with a diameter of 0.8 mm, and dry it in a ventilation dryer at 50°C. This material is sized using a sifter to obtain granules. Formulation Example 2 Granules 35 parts of Compound No. 4 and 35 parts of S-(4-chlorobenzyl)N,N-diethylthiol carbamate were finely ground, 30 parts of white carbon was added thereto, and the mixture was mixed in a mixer. and get premixes. 20 parts of this premix are homogeneously mixed in a mixer with 50 parts of clay and 30 parts of bentonite. Add an appropriate amount of water to this mixture, knead it in a kneader, extrude it through a screen with a diameter of 0.8 mm, and dry it in a ventilation dryer at 50°C. This product is sized using a sifter to obtain mixed granules. Formulation example 3 Wettable powder 50 parts of Compound No. 17, 29 parts of clay, 10 parts of diatomaceous earth, 5 parts of white carbon, 3 parts of sodium lignin sulfonate, 2 parts of Newcol 1106 (trade name of Nippon Nyukazai Co., Ltd.), and polyvinyl alcohol One part was mixed uniformly in a mixer and ground three times in a hammer mill to obtain a wettable powder. Formulation Example 4 Emulsion 20 parts of Compound No. 34, 65 parts of xylene and 15 parts of Pacolar PS (trade name of Nippon Nyukazai Co., Ltd.) are mixed and uniformly dissolved to obtain an emulsion. Test examples of the herbicide of the present invention prepared in this way are given below. The test drug was manufactured according to Formulation Example 3 above, and the active ingredient compound of the present invention was added to the
A hydrating agent containing %. Test example 1 Paddy weed flooded soil treatment test 3 polyethylene pots (A,
Fill pots (abbreviated as B and C) with paddy soil, transplant one (two) seedlings of paddy rice (variety: Kinnanfu) at the 2.5 leaf stage into pot A, and add two tubers of Urikawa to represent perennial weeds. Insert. In pot B, the seeds of Japanese azalea, azalea, and sycamore, representative of broad-leaved weeds, are mixed well with the soil. In addition, I transplanted one growing stock of Pinus spp., and planted two tubers of the perennial weed Cyperus japonica per pot. For Pot C, seeds of Japanese grasshopper and firefly, which are representative of narrow-leaved weeds, are mixed well with the soil. In addition, two tubers of the perennial weed Omodaka are planted per pot.
Pots A, B, and C were cultivated in a greenhouse for 3 days as a paddy field, and after the plants were cultivated, the soil was treated with 10 c.c. of suspension of the test chemical per pot in a flooded state. After 20 days of treatment, the herbicidal effect on each weed and the chemical damage to paddy rice were observed and determined. The results are shown in Table 1. However, the effective dose (g/
a) indicates the lowest drug dose at which the degree of growth inhibition (whitening area on the plant surface) of each plant is 70% or more.
【表】
試験例 2
畑雑草発芽前土壌処理試験
表面積150cm2のポリエチレン製ポツトに畑土壌
を充填し、狭葉雑草の代表としてケイヌビエ、メ
ヒシバ、エノコログサ、オヒシバ、カヤツリグサ
および広葉雑草の代表としてナズナの各種子を播
種して覆土した。
別に、表面積150cm2のポリエチレン製ポツトに
畑土壌を充填し、狭葉雑草のケイヌビエ、メヒシ
バ、エノコログサ、オヒシバ、カヤツリグサ、広
葉雑草のハコベ、ツユクサ、オオツメクサ、イヌ
ビエ、スベリヒユ、シロザ、ナヅナの各種子を播
種して覆土した。
両ポツトとも覆土後直ちに供試薬剤の懸濁液を
ポツトあたり10c.c.ずつ土壌表面に処理した。処理
20日後に各雑草に対する除草効果を観察した。そ
の結果を表2表に示す。ただし、判定基準は試験
例1と同じであり、有効薬量(g/a)で示す。[Table] Test Example 2 Pre-emergence soil treatment test for field weeds A polyethylene pot with a surface area of 150 cm 2 was filled with field soil, and a field soil was added to the field to represent narrow-leaved weeds such as cane millet, cicada, cyperus, cyperus, and broad-leaved weeds. Each seed was sown and covered with soil. Separately, a polyethylene pot with a surface area of 150 cm 2 was filled with field soil, and seeds of narrow-leaved weeds such as cane millet, blackberry, hackberry, cyperus, and cyperus, and broad-leaved weeds such as chickweed, commonweed, common clover, golden millet, purslane, whitewort, and napus were added. The seeds were sown and covered with soil. Immediately after covering both pots with soil, a suspension of the test chemical was applied to the soil surface in an amount of 10 c.c. per pot. process
After 20 days, the herbicidal effect on each weed was observed. The results are shown in Table 2. However, the judgment criteria are the same as in Test Example 1, and are expressed in effective dose (g/a).
Claims (1)
はフエニル基またはハロゲン置換フエニル基を示
し、R1がフエニル基またはホルミル基を示すと
き、R2は低級アルキル基を示す。Xは低級アル
キル基、低級アルコキシ基、ニトロ基またはハロ
ゲン原子を示し、nは0,1または2を示し、n
が2のときXは互いに同一もしくは異なつてもよ
い。)を有する化合物、その塩またはその脂肪族
もしくは芳香族カルボン酸またはスルホン酸エス
テルを有効成分とする除草剤。[Claims] 1 formula (In the formula, when R 1 represents a lower alkyl group, R 2
represents a phenyl group or a halogen-substituted phenyl group, and when R 1 represents a phenyl group or a formyl group, R 2 represents a lower alkyl group. X represents a lower alkyl group, lower alkoxy group, nitro group or halogen atom, n represents 0, 1 or 2, n
When is 2, X may be the same or different from each other. ), a salt thereof, or an aliphatic or aromatic carboxylic acid or sulfonic acid ester thereof as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1122779A JPS55113706A (en) | 1979-02-02 | 1979-02-02 | Herbicide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1122779A JPS55113706A (en) | 1979-02-02 | 1979-02-02 | Herbicide |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS55113706A JPS55113706A (en) | 1980-09-02 |
JPS6128642B2 true JPS6128642B2 (en) | 1986-07-01 |
Family
ID=11772060
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1122779A Granted JPS55113706A (en) | 1979-02-02 | 1979-02-02 | Herbicide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS55113706A (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2738010B2 (en) * | 1988-07-15 | 1998-04-08 | 日産化学工業株式会社 | Pyrazole inducers and selective herbicides |
US5264451A (en) * | 1992-04-07 | 1993-11-23 | American Home Products Corporation | Process for treating hyperglycemia using trifluoromethyl substituted 3H-pyrazol-3-ones |
WO1996024589A1 (en) * | 1995-02-07 | 1996-08-15 | Nissan Chemical Industries, Ltd. | Pyrazole derivatives and herbicides |
JPH09136887A (en) * | 1995-09-13 | 1997-05-27 | Nippon Bayeragrochem Kk | Chloropyridylcarbonyl derivative |
WO2013082756A1 (en) * | 2011-12-06 | 2013-06-13 | Leo Pharma A/S | Phosphate transport inhibitors ii |
WO2013082751A1 (en) * | 2011-12-06 | 2013-06-13 | Leo Pharma A/S | Phosphate transport inhibitors i |
EP3352020B1 (en) * | 2015-09-17 | 2021-06-16 | Hodogaya Chemical Co., Ltd. | Toner and charge control agent using pyrazolone derivative or a salt of said derivative |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50126830A (en) * | 1974-03-28 | 1975-10-06 | ||
JPS51106738A (en) * | 1975-03-12 | 1976-09-21 | Sankyo Co | JOSOZAI |
-
1979
- 1979-02-02 JP JP1122779A patent/JPS55113706A/en active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50126830A (en) * | 1974-03-28 | 1975-10-06 | ||
JPS51106738A (en) * | 1975-03-12 | 1976-09-21 | Sankyo Co | JOSOZAI |
Also Published As
Publication number | Publication date |
---|---|
JPS55113706A (en) | 1980-09-02 |
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