JPS64382B2 - - Google Patents
Info
- Publication number
- JPS64382B2 JPS64382B2 JP9748681A JP9748681A JPS64382B2 JP S64382 B2 JPS64382 B2 JP S64382B2 JP 9748681 A JP9748681 A JP 9748681A JP 9748681 A JP9748681 A JP 9748681A JP S64382 B2 JPS64382 B2 JP S64382B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- lower alkyl
- phenoxy
- propionic acid
- 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
- 150000001875 compounds Chemical class 0.000 claims description 52
- -1 phenoxypropionate ester Chemical class 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 230000002363 herbicidal effect Effects 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000004009 herbicide Substances 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- XIKRHZPYZYARLS-UHFFFAOYSA-N 1-phenylmethoxypropan-2-yl 2-[4-(3,5-dichloropyridin-2-yl)oxyphenoxy]propanoate Chemical compound C=1C=C(OC=2C(=CC(Cl)=CN=2)Cl)C=CC=1OC(C)C(=O)OC(C)COCC1=CC=CC=C1 XIKRHZPYZYARLS-UHFFFAOYSA-N 0.000 claims description 2
- KNOUUEYNFHXIEM-UHFFFAOYSA-N 2-phenylmethoxyethyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C=1C=CC=CC=1COCCOC(=O)C(C)OC(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 KNOUUEYNFHXIEM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- SJSIKMPGHJLKMD-UHFFFAOYSA-N 1-phenylmethoxypropan-2-yl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C=1C=C(OC=2C=CC(=CC=2)C(F)(F)F)C=CC=1OC(C)C(=O)OC(C)COCC1=CC=CC=C1 SJSIKMPGHJLKMD-UHFFFAOYSA-N 0.000 claims 1
- BVPSASAWYIPTIJ-UHFFFAOYSA-N 2-(1-phenylethoxy)ethyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C=1C=CC=CC=1C(C)OCCOC(=O)C(C)OC(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 BVPSASAWYIPTIJ-UHFFFAOYSA-N 0.000 claims 1
- HZRSJETYNMBYKJ-UHFFFAOYSA-N 2-[(2-fluorophenyl)methoxy]ethyl 2-[4-(3,5-dichloropyridin-2-yl)oxyphenoxy]propanoate Chemical compound C=1C=CC=C(F)C=1COCCOC(=O)C(C)OC(C=C1)=CC=C1OC1=NC=C(Cl)C=C1Cl HZRSJETYNMBYKJ-UHFFFAOYSA-N 0.000 claims 1
- CTVLBBBHXAAPPO-UHFFFAOYSA-N 2-[(2-fluorophenyl)methoxy]ethyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C=1C=CC=C(F)C=1COCCOC(=O)C(C)OC(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 CTVLBBBHXAAPPO-UHFFFAOYSA-N 0.000 claims 1
- TZLANYAEIQMUGT-UHFFFAOYSA-N 2-[(4-chlorophenyl)methoxy]ethyl 2-[4-(3,5-dichloropyridin-2-yl)oxyphenoxy]propanoate Chemical compound C=1C=C(Cl)C=CC=1COCCOC(=O)C(C)OC(C=C1)=CC=C1OC1=NC=C(Cl)C=C1Cl TZLANYAEIQMUGT-UHFFFAOYSA-N 0.000 claims 1
- VMAKMZQHRCAKNJ-UHFFFAOYSA-N 2-phenylmethoxyethyl 2-[4-(3,5-dichloropyridin-2-yl)oxyphenoxy]propanoate Chemical compound C=1C=CC=CC=1COCCOC(=O)C(C)OC(C=C1)=CC=C1OC1=NC=C(Cl)C=C1Cl VMAKMZQHRCAKNJ-UHFFFAOYSA-N 0.000 claims 1
- UKGCEYHGLOIEMF-UHFFFAOYSA-N 3-phenylmethoxypropyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C=1C=CC=CC=1COCCCOC(=O)C(C)OC(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 UKGCEYHGLOIEMF-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000012360 testing method Methods 0.000 description 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 24
- 125000001246 bromo group Chemical group Br* 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 21
- 229910052736 halogen Chemical group 0.000 description 19
- 235000019260 propionic acid Nutrition 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 239000002689 soil Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000002367 halogens Chemical group 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- 244000025254 Cannabis sativa Species 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000003905 agrochemical Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 235000016068 Berberis vulgaris Nutrition 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000088415 Raphanus sativus Species 0.000 description 3
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000006501 nitrophenyl group Chemical group 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- 238000009333 weeding Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KJBPYIUAQLPHJG-UHFFFAOYSA-N 1-phenylmethoxypropan-2-ol Chemical compound CC(O)COCC1=CC=CC=C1 KJBPYIUAQLPHJG-UHFFFAOYSA-N 0.000 description 2
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical class OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 2
- MCVIDUDFKDIJMZ-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methoxy]ethanol Chemical compound OCCOCC1=C(Cl)C=CC=C1Cl MCVIDUDFKDIJMZ-UHFFFAOYSA-N 0.000 description 2
- VOTIBUBWWVMJIZ-UHFFFAOYSA-N 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoyl chloride Chemical compound C1=CC(OC(C)C(Cl)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 VOTIBUBWWVMJIZ-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- FJFSSESWAFPCSU-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 FJFSSESWAFPCSU-UHFFFAOYSA-N 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 229940072049 amyl acetate Drugs 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound 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 2
- 235000021240 caseins Nutrition 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
- 239000002734 clay mineral Substances 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound 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 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000005599 propionic acid derivatives Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9748681A JPS57212144A (en) | 1981-06-25 | 1981-06-25 | Substituted phenoxypropionic ester, its preparation, and herbicide |
| PH27376A PH18417A (en) | 1981-06-25 | 1982-05-31 | Substituted phenoxypropionates and herbicidal compositions |
| DE8282105172T DE3269600D1 (en) | 1981-06-25 | 1982-06-14 | Substituted phenoxypropionates, process for their preparation and their use as herbicides |
| EP82105172A EP0068260B1 (de) | 1981-06-25 | 1982-06-14 | Substituierte Phenoxypropionate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| AT82105172T ATE18390T1 (de) | 1981-06-25 | 1982-06-14 | Substituierte phenoxypropionate, verfahren zu ihrer herstellung und ihre verwendung als herbizide. |
| PT75053A PT75053B (en) | 1981-06-25 | 1982-06-15 | Process for the preparation of an herbicidal composition containing substituted phenoxypropionates |
| US06/389,525 US4441913A (en) | 1981-06-25 | 1982-06-17 | Substituted phenoxypropionates and herbicidal compositions |
| IL7320382A IL73203A (en) | 1981-06-25 | 1982-06-22 | Benzyloxyalkyl-2-halopropionates and their preparation |
| IL66096A IL66096A (en) | 1981-06-25 | 1982-06-22 | Benzyloxyalkyl esters of substituted 4-phenoxy and 4-pyridinyloxy phenoxypropionic acids,their preparation and their use as herbicides |
| AU85091/82A AU556522B2 (en) | 1981-06-25 | 1982-06-22 | Phenoxypropionate esters, herbicides |
| NZ201042A NZ201042A (en) | 1981-06-25 | 1982-06-22 | Substituted phenoxypropionates and herbicidal compositions |
| DD82240964A DD202087A5 (de) | 1981-06-25 | 1982-06-22 | Herbizide mittel |
| GR68546A GR76837B (pl) | 1981-06-25 | 1982-06-23 | |
| CA000405784A CA1175839A (en) | 1981-06-25 | 1982-06-23 | Substituted phenoxypropionates and herbicidal compositions |
| TR21452A TR21452A (tr) | 1981-06-25 | 1982-06-23 | Yeni suebstitueye fenoksipropionatlar,bunlarin hazirlanisi icin bir usul ve yeni ara ueruenler ve bunlarin herbisidler olarak kullanilmalari |
| ZA824488A ZA824488B (en) | 1981-06-25 | 1982-06-24 | Novel substituted phenoxypropionates, a process and new intermediates for their preparation and their use as herbicides |
| CS471182A CS229683B2 (en) | 1981-06-25 | 1982-06-24 | Herbicide agent and manufacturing process of effective component |
| BR8203706A BR8203706A (pt) | 1981-06-25 | 1982-06-24 | Processo para a preparacao de fenoxipropionatos substituidos composicoes herbicidas e processo para o combate de ervas daninhas |
| PL23708782A PL134782B1 (en) | 1981-06-25 | 1982-06-24 | Herbicide and method of obtaining new substituted phenoxyproprionates |
| DK285782A DK285782A (da) | 1981-06-25 | 1982-06-24 | Substituerede phenoxypropionater fremgangsmaader samt mellemprodukter til fremstilling heraf og deres anvendelse som herbicider |
| ES513476A ES513476A0 (es) | 1981-06-25 | 1982-06-25 | Procedimiento para la obtencion de fenoxipropionatos sustituidos. |
| HU822065A HU189596B (en) | 1981-06-25 | 1982-06-25 | Herbicide compositions containing new substituted phenoxy-propionates as active agents and process for producing the active agents |
| KR8202834A KR880002413B1 (ko) | 1981-06-25 | 1982-06-25 | 페녹시프로피오네이트 제조방법 |
| CS831993A CS229699B2 (cs) | 1981-06-25 | 1983-03-23 | Způsob výroby nových substituovaných fenoxypropionátů |
| ES522324A ES522324A0 (es) | 1981-06-25 | 1983-05-12 | Procedimiento para la obtencion de 2-(4-hidroxifenoxi)-propionatos. |
| ES83522322A ES522322A0 (es) | 1981-06-25 | 1983-05-12 | Procedimiento para la obtencion de fenoxipropionatos sustituidos. |
| ES522323A ES8406999A1 (es) | 1981-06-25 | 1983-05-12 | Procedimiento para la obtencion de 2-halogenopropionatos sustituidos. |
| US06/546,216 US4584396A (en) | 1981-06-25 | 1983-12-12 | Substituted phenoxypropionates and herbicidal compositions |
| CA000444790A CA1234142A (en) | 1981-06-25 | 1984-01-05 | Substituted 2-halogenopropionates as intermediates for herbicides |
| IL73203A IL73203A0 (en) | 1981-06-25 | 1984-10-09 | Substituted 2-halopropionates and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9748681A JPS57212144A (en) | 1981-06-25 | 1981-06-25 | Substituted phenoxypropionic ester, its preparation, and herbicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57212144A JPS57212144A (en) | 1982-12-27 |
| JPS64382B2 true JPS64382B2 (pl) | 1989-01-06 |
Family
ID=14193598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9748681A Granted JPS57212144A (en) | 1981-06-25 | 1981-06-25 | Substituted phenoxypropionic ester, its preparation, and herbicide |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS57212144A (pl) |
| CS (1) | CS229683B2 (pl) |
| PL (1) | PL134782B1 (pl) |
| ZA (1) | ZA824488B (pl) |
-
1981
- 1981-06-25 JP JP9748681A patent/JPS57212144A/ja active Granted
-
1982
- 1982-06-24 CS CS471182A patent/CS229683B2/cs unknown
- 1982-06-24 PL PL23708782A patent/PL134782B1/pl unknown
- 1982-06-24 ZA ZA824488A patent/ZA824488B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL237087A1 (en) | 1984-05-21 |
| ZA824488B (en) | 1983-04-27 |
| JPS57212144A (en) | 1982-12-27 |
| CS229683B2 (en) | 1984-06-18 |
| PL134782B1 (en) | 1985-09-30 |
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