JPH0446169A - New benzofuran derivative and herbicide containing same derivative - Google Patents
New benzofuran derivative and herbicide containing same derivativeInfo
- Publication number
- JPH0446169A JPH0446169A JP15391090A JP15391090A JPH0446169A JP H0446169 A JPH0446169 A JP H0446169A JP 15391090 A JP15391090 A JP 15391090A JP 15391090 A JP15391090 A JP 15391090A JP H0446169 A JPH0446169 A JP H0446169A
- Authority
- JP
- Japan
- Prior art keywords
- group
- optionally substituted
- groups
- carbon atoms
- compound
- 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.)
- Pending
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 17
- 239000004009 herbicide Substances 0.000 title claims abstract description 15
- 150000001907 coumarones Chemical class 0.000 title claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 19
- 239000004480 active ingredient Substances 0.000 claims description 14
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 4
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 53
- 125000003118 aryl group Chemical group 0.000 abstract description 21
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 125000005843 halogen group Chemical group 0.000 abstract description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 6
- 239000003513 alkali Substances 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 3
- 239000002585 base Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 49
- -1 3-chloroproyl group Chemical group 0.000 description 35
- 125000002947 alkylene group Chemical group 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- 125000004429 atom Chemical group 0.000 description 14
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 229940124530 sulfonamide Drugs 0.000 description 9
- 150000003456 sulfonamides Chemical class 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 241000218691 Cupressaceae Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 238000003973 irrigation Methods 0.000 description 5
- 230000002262 irrigation Effects 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-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
- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241000254158 Lampyridae Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000005243 carbonyl alkyl group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000008282 halocarbons Chemical class 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
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- WHXAHMHWAOFQMS-UHFFFAOYSA-N n,3,3-trimethyl-2h-1-benzofuran-5-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C2OCC(C)(C)C2=C1 WHXAHMHWAOFQMS-UHFFFAOYSA-N 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
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene 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
- 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
- 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
- SXFQAFFSEZRQCJ-UHFFFAOYSA-N 1-benzofuran-5-carbonitrile Chemical class N#CC1=CC=C2OC=CC2=C1 SXFQAFFSEZRQCJ-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- XXXFZKQPYACQLD-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl acetate Chemical compound CC(=O)OCCOCCO XXXFZKQPYACQLD-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- VURUNMWLBDYAMB-UHFFFAOYSA-N 2-butylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CCCC)=CC=C21 VURUNMWLBDYAMB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241001638133 Bidyanus welchi Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 108010076119 Caseins Proteins 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229920002871 Dammar gum Polymers 0.000 description 1
- 239000004860 Dammar gum Substances 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000287116 Paridae Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- YVBSAPDHRXHFHV-UHFFFAOYSA-N [chloro(methoxy)methyl]benzene Chemical compound COC(Cl)C1=CC=CC=C1 YVBSAPDHRXHFHV-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical 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 1
- 235000021240 caseins Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical group O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 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
- DWHOIYXAMUMQTI-UHFFFAOYSA-L disodium;2-[(1-sulfonatonaphthalen-2-yl)methyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC2=CC=CC=C2C(S(=O)(=O)[O-])=C1CC1=CC=C(C=CC=C2)C2=C1S([O-])(=O)=O DWHOIYXAMUMQTI-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000010985 glycerol esters of wood rosin Nutrition 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 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
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 239000003350 kerosene Substances 0.000 description 1
- 239000011419 magnesium lime Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-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
- HWWVAHCWJLGKLW-UHFFFAOYSA-N n,n-dimethylhydroxylamine;hydron;chloride Chemical compound Cl.CN(C)O HWWVAHCWJLGKLW-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
- 229920005615 natural polymer Polymers 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 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
- 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
- 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
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 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
- 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
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-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
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009333 weeding Methods 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
Landscapes
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
(産業上の利用分野)
本発明は、新規なベンゾフラン誘導体及びこれを有効成
分として含有する除草剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel benzofuran derivative and a herbicide containing the same as an active ingredient.
(従来の技術及び発明が解決しようとする課題)従来、
特開昭55−20788号公報に、2゜3−ジヒドロ−
5−シアノベンゾフラン化合物が除草剤の有効成分とし
て用うろことが記載され公知である。(Prior art and problems to be solved by the invention) Conventionally,
In JP-A No. 55-20788, 2゜3-dihydro-
The use of 5-cyanobenzofuran compounds as active ingredients in herbicides has been described and is known.
しかしながら、これらの化合物は、除草効力が不十分で
あっt;す、作物・雑草間の選択性に劣っt;すするこ
とから、必ずしも満足すべきものとは言い難い。However, these compounds are not necessarily satisfactory because they have insufficient herbicidal efficacy and poor selectivity between crops and weeds.
(課題を解決するための手段)
本発明者らは、わずかな施用量でも好ましくない植物に
対して優れた除草効果を有し、かつ、作物・雑草間に高
度の選択性を示す化合物を提供すべく、種々研究した結
果、下記の一般式(I)で示されるベンゾフラン誘導体
を見い出し、本発明に到達した。(Means for Solving the Problems) The present inventors provide a compound that has an excellent herbicidal effect against undesirable plants even at a small application amount, and shows a high degree of selectivity between crops and weeds. As a result of various studies, a benzofuran derivative represented by the following general formula (I) was discovered, and the present invention was achieved.
すなわち、本発明は、−船蔵(1)
[式中、R′、R2は同一でも異なってもよく水素原子
または低級アルキル基を表わし、R1は水素原子、低級
アルキル基、低級ハロアルキル基、低級シアノアルキル
基、低級アルケニル基、低級アルキニル基、置換されて
もよいアリール基まt:は置換されてもよいアラルキル
基を表わし、R4はヒドロキシ基、低級ハロアルキル基
、低級シアノアルキル基、低級アルケニル基、低級アル
キニル基、置換されてもよいアリール基、置換されても
よいアラルキル基、低級アルコキシ基、置換されてもよ
いアリールオキシ基、置換されてもよいアラルキルオキ
シ基、アルコキシアルキル基、置換されてもよいアリー
ルオキシアルキル基、置換されてもよいアラルキルオキ
シアルキル基、アルキルカルボニル基、置換されてもよ
いアリールカルボニル基、置換されてもよいアラルキル
カルボニル基、アルキルカルボニルアルキル基、置換さ
れてもよいアリールカルボニルアルキル基、置換されて
もよいアラルキルカルボニルアルキル基、アルコキシカ
ルボニル基、置換されてもよいアリールオキシカルボニ
ル基、置換されてもよいアラルキルオキシカルボニル基
、アルコキシカルボニルアルキル基、置換されてもよい
アリールオキシカルボニルアルキル基、置換されてもよ
いアラルキルオキシカルボニルアルキル基またはアルコ
キシカルボニルアルコキシ基を表わす。]で表わされる
新規ベンゾフラン誘導体である。That is, the present invention provides - Funazura (1) [wherein R' and R2 may be the same or different and represent a hydrogen atom or a lower alkyl group, and R1 is a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower cyanoalkyl group, lower alkenyl group, lower alkynyl group, optionally substituted aryl group or t: represents optionally substituted aralkyl group, R4 is hydroxy group, lower haloalkyl group, lower cyanoalkyl group, lower alkenyl group , lower alkynyl group, optionally substituted aryl group, optionally substituted aralkyl group, lower alkoxy group, optionally substituted aryloxy group, optionally substituted aralkyloxy group, alkoxyalkyl group, substituted optionally substituted aryloxyalkyl group, optionally substituted aralkyloxyalkyl group, alkylcarbonyl group, optionally substituted arylcarbonyl group, optionally substituted aralkylcarbonyl group, alkylcarbonylalkyl group, optionally substituted aryl Carbonylalkyl group, optionally substituted aralkylcarbonylalkyl group, alkoxycarbonyl group, optionally substituted aryloxycarbonyl group, optionally substituted aralkyloxycarbonyl group, alkoxycarbonylalkyl group, optionally substituted aryloxy Represents a carbonylalkyl group, an optionally substituted aralkyloxycarbonylalkyl group, or an alkoxycarbonylalkoxy group. ] is a new benzofuran derivative.
前記一般式(I)においてR1,Rjが低級アルキル基
である場合、その例としては、炭素数1〜3の低級アル
キル基が好ましく、例えばメチル基、エチル基、n−プ
ロピル基、イソプロピル基などを挙げることができる。In the general formula (I), when R1 and Rj are lower alkyl groups, preferred examples thereof include lower alkyl groups having 1 to 3 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, etc. can be mentioned.
前記一般式(1)におけるR18よびR6の具体的な原
子または基について以下列挙する。Specific atoms or groups of R18 and R6 in the general formula (1) are listed below.
R3の具体的:
(i)水素原子;
(■)低級アルキル基、低級アルケニル基および低級ア
ルキニル基:
炭素数1ないし5のものが好ましく、例えばメチル基、
エチル基、n−プロピル基、イソプロピル基、n−ブチ
ル基、t−ブチル基、ネオペンチル基、アリル基、メタ
アリル基、クロチル基、プロパルギル基、2−ブチニル
基などを挙げることができる。Specifics of R3: (i) Hydrogen atom; (■) Lower alkyl group, lower alkenyl group, and lower alkynyl group: Those having 1 to 5 carbon atoms are preferred, such as methyl group,
Examples include ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, neopentyl group, allyl group, metaallyl group, crotyl group, propargyl group, and 2-butynyl group.
(ii)低級ハロアルキル基:
炭素数1ないし5のハロアルキル基が好ましく、例えば
2.2.2−トリフルオロエチル基、2−クロロエチル
基、3−クロロプロヒルi&、2−ブロモエチル基、3
−ブロモプロピル基などを挙げることができる。(ii) Lower haloalkyl group: A haloalkyl group having 1 to 5 carbon atoms is preferable, such as 2.2.2-trifluoroethyl group, 2-chloroethyl group, 3-chloroproyl group, 2-bromoethyl group, 3
-bromopropyl group and the like.
(iv)低級シアノアルキル基;
炭素数1ないし5の直鎖または分岐のアルキレン部を有
するシアノアルキル基が好ましい。(iv) Lower cyanoalkyl group: A cyanoalkyl group having a linear or branched alkylene moiety having 1 to 5 carbon atoms is preferred.
(v)置換されてもよいアリール基および置換されても
よいアラルキル基:
これらアリール基及びアラルキル基を形成するアリール
部としては、ベンゼン環、ピリジン環、7ラン環または
チオフェン環が好ましい。これらのアリール部は1個ま
たはそれ以上、好ましくは1個〜3個の原子または基に
より置換されてもよい。置換されうる原子または基とし
ては、ハロゲン原子、炭素数l〜3の低級アルキル基、
炭素数1〜3の低級ハロアルキル基、炭素数1〜3の低
級アルコキシ基、ニトロ基などが挙げられ、フッ素原子
、塩素原子、臭素原子、メチル基、エチル基、n−プロ
ピル基、イソプロピル基、トリフルオロメチル基、メト
キシ基、エトキシ基、インプロポキシ基、ニトロ基が好
ましい。アラルキル基のアルキレン部としては炭素数1
〜5の直鎖または分岐の低級アルキレンが好ましい。(v) Aryl group that may be substituted and aralkyl group that may be substituted: The aryl moiety forming these aryl groups and aralkyl groups is preferably a benzene ring, a pyridine ring, a 7-ran ring, or a thiophene ring. These aryl moieties may be substituted by one or more, preferably from 1 to 3 atoms or groups. Atoms or groups that can be substituted include halogen atoms, lower alkyl groups having 1 to 3 carbon atoms,
Examples include lower haloalkyl groups having 1 to 3 carbon atoms, lower alkoxy groups having 1 to 3 carbon atoms, nitro groups, and fluorine atoms, chlorine atoms, bromine atoms, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, Trifluoromethyl, methoxy, ethoxy, impropoxy, and nitro groups are preferred. The alkylene part of the aralkyl group has 1 carbon number
~5 linear or branched lower alkylene is preferred.
R1の具体例:
(+)ヒドロキシ基(OH)、
(2)低級ハロアルキル基;
炭素数1〜5のハロアルキル基が好ましく、例えば2.
2.2−)リフルオロエチル基、2−クロロエチル基、
3−クロロプロピル基、2−ブロモエチル基、3−ブロ
モプロピル基などを挙げることができる。Specific examples of R1: (+) hydroxy group (OH), (2) lower haloalkyl group; A haloalkyl group having 1 to 5 carbon atoms is preferred, for example 2.
2.2-) Lifluoroethyl group, 2-chloroethyl group,
Examples include 3-chloropropyl group, 2-bromoethyl group, and 3-bromopropyl group.
(3)°低級シアノアルキル基:
炭素数lないし5の直鎖または分岐のアルキレン部を有
するシアノアルキル基が好ましい。(3) Lower cyanoalkyl group: A cyanoalkyl group having a linear or branched alkylene moiety having 1 to 5 carbon atoms is preferred.
(4)低級アルケニル基および低級アルキニル基;
炭素数1ないし5のものが好ましく、例えばアリル基、
メタアリル基、クロチル、プロパルギル基、2−ブチニ
ル基などを挙げることができる。(4) Lower alkenyl group and lower alkynyl group; preferably those having 1 to 5 carbon atoms, such as allyl group,
Examples include metaallyl group, crotyl group, propargyl group, and 2-butynyl group.
(5)置換されてもよいアリール基および置換されでも
よいアラルキル基;
これらアリール基及びアラルキル基を形成するアリール
部としては、ベンゼン環、ピリジン環、フラン環まI;
はチオフェン環が好ましい。これらのアリール部は1個
またはそれ以上、好まし・:は1個〜3個の原子または
基により置換されていてもよい。It換されうる原子ま
たは基として、ハロゲン原子、炭素数1〜3の低級アル
キル基、炭素数1〜3の低級ハロアルキル基、炭素数1
〜3の低級アルコキシ基、ニトロ基などが挙げられ、フ
ッ素原子、塩素原子、臭素原子、メチル基、エチル基、
n−プロピル基、イソプロピル基、トリフルオロメチル
基、メトキシ基、エトキシ基、インプロポキシ基、ニト
ロ基が好ましい。(5) An optionally substituted aryl group and an optionally substituted aralkyl group; The aryl moiety forming these aryl groups and aralkyl groups includes a benzene ring, a pyridine ring, a furan ring, or I;
is preferably a thiophene ring. These aryl moieties may be substituted with one or more atoms or groups, preferably 1 to 3 atoms or groups. Examples of atoms or groups that can be replaced with It include halogen atoms, lower alkyl groups having 1 to 3 carbon atoms, lower haloalkyl groups having 1 to 3 carbon atoms, and 1 carbon atoms.
~3 lower alkoxy groups, nitro groups, etc., fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group,
Preferred are n-propyl group, isopropyl group, trifluoromethyl group, methoxy group, ethoxy group, impropoxy group, and nitro group.
一方前記アラルキル基のアルキレン部としては炭素数1
〜5の直鎖または分岐の低級アルキレンが好ましい。On the other hand, the alkylene moiety of the aralkyl group has 1 carbon number
~5 linear or branched lower alkylene is preferred.
このアルキレン部は1個またはそれ以上の原子または基
により置換され得る。その例としては、ハロゲン原子、
炭素数1〜3の低級アルコキシ基、炭素数1〜5の低級
アルコキンカルボニル基またはンアノ基などが挙げられ
、フッ素原子、塩素原子、臭素原子、メトキシ基、エト
キシ基、n−プロポキシ基、メトキシカルボニル基、エ
トキシカルボニル基、シアノ基が好ましい。The alkylene moiety may be substituted with one or more atoms or groups. Examples include halogen atoms,
Examples include a lower alkoxy group having 1 to 3 carbon atoms, a lower alkoxycarbonyl group having 1 to 5 carbon atoms, or an ano group; fluorine atom, chlorine atom, bromine atom, methoxy group, ethoxy group, n-propoxy group, methoxy A carbonyl group, an ethoxycarbonyl group, and a cyano group are preferred.
(6)低級アルコキシ基:
炭素数1〜5の低級アルコキシ基が好ましく、例えばメ
トキシ基、エトキシ基、n−プロポキシ基、インプロポ
キシ基などが挙げられる。(6) Lower alkoxy group: A lower alkoxy group having 1 to 5 carbon atoms is preferred, and examples thereof include methoxy group, ethoxy group, n-propoxy group, and impropoxy group.
(7)置換されてもよいアリールオキシ基および置換さ
れてもよいアラルキルオキシ基:これらアリールオキシ
基およびアラルキルオキシ基を形成するアリール部とし
ては、ベンゼン環、ピリジン環、7ラン環またはチオフ
ェン環が好ましい。これらのアリール部は1個またはそ
れ以上の原子まI;は基により置換され得るがその例と
しては、例えばハロゲン原子、炭素数1〜3の低級アル
キル基、炭素数l〜3の低級ハロアルキル基、炭素数1
〜3の低級アルコキシ基、ニトロ基などが挙げられ、フ
ッ素原子、塩素原子、臭素原子、メチル基、エチル基、
n−プロピル基、イソプロピル基、トリフルオロメチル
基、メトキン基、エトキシ基、インプロポキシ基、ニト
ロ基が好ましい。(7) An optionally substituted aryloxy group and an optionally substituted aralkyloxy group: The aryl moiety forming these aryloxy groups and aralkyloxy groups includes a benzene ring, a pyridine ring, a heptad ring, or a thiophene ring. preferable. These aryl moieties may be substituted with one or more atoms or groups, such as halogen atoms, lower alkyl groups having 1 to 3 carbon atoms, and lower haloalkyl groups having 1 to 3 carbon atoms. , carbon number 1
~3 lower alkoxy groups, nitro groups, etc., fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group,
Preferred are n-propyl group, isopropyl group, trifluoromethyl group, metquine group, ethoxy group, impropoxy group, and nitro group.
一方前記アラルキルオキシ基のアルキレン部としては炭
素数l〜5の直鎖または分岐の低級アルキレンが好まし
い。On the other hand, the alkylene moiety of the aralkyloxy group is preferably a linear or branched lower alkylene having 1 to 5 carbon atoms.
(8)アルコキシアルキル基:
アルコキシ部としては炭素数1〜5の低級アルコキシ基
が好ましく、例えばメトキシ基、エトキシ基、n−プロ
ポキシ基、インプロポキシ基などを挙げることができる
。アルコキシアルキル基のアルキレン部としては炭素数
1〜5の直鎖または分岐の低級アルキレンが好ましい。(8) Alkoxyalkyl group: The alkoxy moiety is preferably a lower alkoxy group having 1 to 5 carbon atoms, such as a methoxy group, an ethoxy group, an n-propoxy group, an inpropoxy group, and the like. The alkylene moiety of the alkoxyalkyl group is preferably a linear or branched lower alkylene having 1 to 5 carbon atoms.
(9)置換されてもよいアリールオキシアルキル基およ
び置換されてもよいアラルキルオキ・ンアルキル基:
これらの基を形成しているアリール部としては、ベンゼ
ン環、ピリジン環、フラン環またはチオフェン環が好ま
しい。これらのアリール部は、1個またはそれ以上の原
子または基により置換され得るが、その例としては、ハ
ロゲン原子、炭素数l〜3の低級アルキル基、炭素数l
〜3の低級ハロアルキル基、炭素数l〜3の低級アルコ
キシ基、ニトロ基などが挙げられ、フッ素原子、塩素原
子、臭素原子、メチル基、エチル基、n−プロピル基、
インプロピル基、トリフルオロメチル基、メトキシ基、
エトキシ基、インプロポキシ基、ニトロ基が好ましい。(9) Optionally substituted aryloxyalkyl group and optionally substituted aralkyloxyalkyl group: The aryl moiety forming these groups is preferably a benzene ring, pyridine ring, furan ring or thiophene ring. . These aryl moieties may be substituted with one or more atoms or groups, such as halogen atoms, lower alkyl groups having 1 to 3 carbon atoms, and 1 to 3 carbon atoms.
-3 lower haloalkyl groups, lower alkoxy groups having 1 to 3 carbon atoms, nitro groups, etc., fluorine atoms, chlorine atoms, bromine atoms, methyl groups, ethyl groups, n-propyl groups,
Inpropyl group, trifluoromethyl group, methoxy group,
Ethoxy, impropoxy and nitro groups are preferred.
アリールオキシアルキル基のフルキレン部およびアラル
キルオキシアルキル基のアルキレン部としては各々炭素
数l〜5の直鎖または分岐の低級アルキレンが好ましい
。The fullkylene moiety of the aryloxyalkyl group and the alkylene moiety of the aralkyloxyalkyl group are each preferably a linear or branched lower alkylene having 1 to 5 carbon atoms.
(10)アルキルカルボニル基:
アルキルカルボニル基のアルキル部としては炭素数1〜
5の低級アルキル基が好ましく、例えば、メチル基、エ
チル基、n−プロピル基、イソプロピル基、n−ブチル
基などが挙げられる。(10) Alkylcarbonyl group: The alkyl part of the alkylcarbonyl group has 1 to 1 carbon atoms.
A lower alkyl group of 5 is preferable, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group.
(II) R換されてもよいアリールカルボニル基およ
び置換されてもよいアラルキルカルボニル基;
これらの基を形成しているアリール部としては、ベンゼ
ン環、ピリジン環、7ラン環またはチオフェン環が好ま
しい。これらのアリール部は、Jfjiまたはそれ以上
の原子まI−は基により置換され得るが、その例として
は、ハロゲン原子、炭素数1〜3の低級アルキル基、炭
素数1〜3の低級ハロアルキル基、炭素数1〜3の低級
アルコキシ基、ニトロ基などが挙げられ、77素原子、
塩素原子、臭素原子、メチル基、エチル基、n−プロピ
ル基、イソプロピル基、トリフルオロメチル基、メトキ
シ基、エトキシ基、インプロポキシ基、ニトロ基が好ま
しい。アラルキルカルボニル基のアルキレン部としては
炭素数1〜5の直鎖または分岐の低級アルキレンが好ま
しい。(II) Arylcarbonyl group which may be substituted with R and aralkylcarbonyl group which may be substituted; The aryl moiety forming these groups is preferably a benzene ring, a pyridine ring, a heptad ring or a thiophene ring. These aryl moieties may be substituted with Jfji or more atoms or groups, such as halogen atoms, lower alkyl groups having 1 to 3 carbon atoms, lower haloalkyl groups having 1 to 3 carbon atoms. , a lower alkoxy group having 1 to 3 carbon atoms, a nitro group, etc., with 77 atoms,
Preferred are a chlorine atom, a bromine atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, an inpropoxy group, and a nitro group. The alkylene moiety of the aralkylcarbonyl group is preferably a straight chain or branched lower alkylene having 1 to 5 carbon atoms.
(+2)アルキルカルボニルアルキル基:この基におけ
るアルキル部としては、炭素数lないし5の低級アルキ
ル基が好ましく、例えば、メチル基、エチル基、n−プ
ロピル基、イソプロピル基、n−ブチル基、などが挙げ
られる。一方アルキル力ルポニルアルキル基のアルキレ
ン部としては、炭素数1ないし5の直鎖または分岐の低
級アルキレンが好ましい。(+2) Alkylcarbonylalkyl group: The alkyl moiety in this group is preferably a lower alkyl group having 1 to 5 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, etc. can be mentioned. On the other hand, the alkylene moiety of the alkyl group is preferably a linear or branched lower alkylene having 1 to 5 carbon atoms.
(13)lit換されてもよいアリールカルボニルアル
キル基および置換されてもよいアラルキルカルボニルア
ルキル基;
これらの基を形成しているアリール部としては、ベンゼ
ン環、ピリジン環、7ラン環またはチオフェン環が好ま
しい。これらのアリール部は、1個またはそれ以上の原
子または基により置換され得るが、その例としては、ハ
ロゲン原子、炭素数1〜3の低級アルキル基、炭素数1
〜3の低級ハロアルキル基、炭素数1〜3の低級アルコ
キシ基、ニトロ基などが挙げられ、フッ素原子、塩素原
子、臭素原子、メチル基、エチル基、n−プロピル基、
イソプロピル基、トリフルオロメチル基、メトキシ基、
エトキシ基、イソプロポキシ基、ニトロ基が好ましい。(13) An optionally substituted arylcarbonylalkyl group and an optionally substituted aralkylcarbonylalkyl group; As the aryl moiety forming these groups, a benzene ring, a pyridine ring, a heptad ring or a thiophene ring is used. preferable. These aryl moieties may be substituted with one or more atoms or groups, such as halogen atoms, lower alkyl groups having 1 to 3 carbon atoms, and 1 to 3 carbon atoms.
-3 lower haloalkyl group, lower alkoxy group having 1 to 3 carbon atoms, nitro group, etc., fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group, n-propyl group,
Isopropyl group, trifluoromethyl group, methoxy group,
Ethoxy, isopropoxy and nitro groups are preferred.
アリールカルボニルアルキル基のアルキレン部及びアラ
ルキルカルボニルアルキル基のアルキレン部としては、
各々、炭素数1〜5の直鎖または分岐の低級アルキレン
が好ましい。As the alkylene part of the arylcarbonylalkyl group and the alkylene part of the aralkylcarbonylalkyl group,
Each of them is preferably a linear or branched lower alkylene having 1 to 5 carbon atoms.
(14)アルコキ/カルボニル基:
この基におけるアルコキン部としては炭素数1〜5の低
級アルコキン基が好ましく、例えばメトキシ基、エトキ
シ基、n−プロポキシ基、インプロポキシ基などが挙げ
られる。(14) Alkokyne/carbonyl group: The alkoxy moiety in this group is preferably a lower alkoxy group having 1 to 5 carbon atoms, such as a methoxy group, an ethoxy group, an n-propoxy group, an impropoxy group, and the like.
(15)置換されてもよいアリールオキシカルボニル基
および置換されてもよいアラルキルオキン力ルボニル基
;
これらの基を形成しているアリール部としては、ベンゼ
ン環、ピリジン環、フラン環またはチオフェン環が好ま
しい。これらのアリール部は、1個またはそれ以上の原
子または基により置換され得るが、その例としては、ハ
ロゲン原子、炭素数1〜3の低級アルキル基、炭素数1
〜3の低級ハロアルキル基、炭素数1〜3の低級アルコ
キシ基、ニトロ基などが挙げられ、フッ素原子、塩素原
子、臭素原子、メチル基、エチル基、n−プロピル基、
イソプロピル基、トリフルオロメチル基、メトキシ基、
エトキシ基、インプロポキシ基、ニトロ基が好ましい。(15) An optionally substituted aryloxycarbonyl group and an optionally substituted aralkyloxycarbonyl group; The aryl moiety forming these groups includes a benzene ring, a pyridine ring, a furan ring, or a thiophene ring. preferable. These aryl moieties may be substituted with one or more atoms or groups, such as halogen atoms, lower alkyl groups having 1 to 3 carbon atoms, and 1 to 3 carbon atoms.
-3 lower haloalkyl group, lower alkoxy group having 1 to 3 carbon atoms, nitro group, etc., fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group, n-propyl group,
Isopropyl group, trifluoromethyl group, methoxy group,
Ethoxy, impropoxy and nitro groups are preferred.
一方アラルキルオキシ力ルポニル基のアルキレン部とし
ては、炭素数1〜5の直鎖または分岐の低級アルキレン
が好ましい。On the other hand, the alkylene moiety of the aralkyloxyluponyl group is preferably a linear or branched lower alkylene having 1 to 5 carbon atoms.
(16)アルコキシカルボニルアルキル基:この基にお
けるアルコキシ部としては、炭素数1ないし5の低級ア
ルコキシ基が好ましく、・倒えばメトキシ基、エトキシ
基、n−プロポキシ基、インプロポキシ基などが挙げら
れる。一方このアルコキシカルボニルアルキル基のアル
キレン部としては炭素1〜5の直鎖まt;は分岐の低級
アルキレンが好ましい。(16) Alkoxycarbonylalkyl group: The alkoxy moiety in this group is preferably a lower alkoxy group having 1 to 5 carbon atoms, and examples thereof include methoxy, ethoxy, n-propoxy, and impropoxy groups. On the other hand, the alkylene moiety of this alkoxycarbonylalkyl group is preferably a linear or branched lower alkylene having 1 to 5 carbon atoms.
(17)置換されてもよいアリールオキシカルボニルア
ルキル基および置換されていてもよいアラルキルオキシ
カルボニルアルキル基;
これらの基を形成しているアリール部としては、ベンゼ
ン環、ピリジン環、7ラン環まt;はチオフェン環が好
ましい。これらのアリール部は、1個またはそれ以上の
原子または基により置換され得るが、その例としては、
ハロゲン原子、炭素数l〜3の低級アルキル基、炭素数
1〜3の低級ハロアルキル基、炭素数1〜3の低級アル
コキシ基、ニトロ基などが挙げられ、フッ素原子、塩素
原子、臭素原子、メチル基、エチル基、n−プロピル基
、イソプロピル基、トリフルオロメチル基、メトキシ基
、エトキシ基、イソプロポキン基、ニトロ基が好ましい
。アリールオキシカルボニルアルキル基のアルキレン部
及びアラルキルオキシカルボニルアルキル基のアルキレ
ン部としては、各々炭素数l〜5の直鎖または分岐の低
級アルキレンが好ましい。(17) An optionally substituted aryloxycarbonylalkyl group and an optionally substituted aralkyloxycarbonylalkyl group; The aryl moiety forming these groups includes a benzene ring, a pyridine ring, a heptad ring, or ; is preferably a thiophene ring. These aryl moieties may be substituted with one or more atoms or groups, examples of which include:
Examples include halogen atoms, lower alkyl groups having 1 to 3 carbon atoms, lower haloalkyl groups having 1 to 3 carbon atoms, lower alkoxy groups having 1 to 3 carbon atoms, nitro groups, fluorine atoms, chlorine atoms, bromine atoms, methyl Preferred are ethyl group, n-propyl group, isopropyl group, trifluoromethyl group, methoxy group, ethoxy group, isopropoquine group, and nitro group. The alkylene moiety of the aryloxycarbonylalkyl group and the alkylene moiety of the aralkyloxycarbonylalkyl group are each preferably a linear or branched lower alkylene having 1 to 5 carbon atoms.
(18)アルコキシカルボニルアルコキシ基;この基に
おけるアルコキシ部としては、炭素数1〜5の低級アル
コキシ基が好ましく、例えばメトキシ基、エトキシ基、
n−プロピル基、イソプロピル基などが挙げられる。一
方アルキレン部としては、炭素数l〜3の直鎖または分
岐の低級アルキレンが好ましい。(18) Alkoxycarbonylalkoxy group; the alkoxy moiety in this group is preferably a lower alkoxy group having 1 to 5 carbon atoms, such as a methoxy group, an ethoxy group,
Examples include n-propyl group and isopropyl group. On the other hand, as the alkylene moiety, a linear or branched lower alkylene having 1 to 3 carbon atoms is preferable.
勿論、前記−船蔵(I)で表わされる化合物において、
光学異性体が存在するものについては、ラセミ体のみな
らずその光学異性体も本発明の範囲内に含まれることを
理解すべきである。Of course, in the compound represented by -Funazou (I),
Where optical isomers exist, it should be understood that not only the racemate but also the optical isomers are included within the scope of the present invention.
前記−船蔵(1)で表わされる本発明の化合物の具体例
を表1に例示する。表中、光学異性体が存在するものに
ついて、(R)または(S)と表記されたものは各々R
体、5体を表わし、無記載のものはラセミ体を表わす。Specific examples of the compound of the present invention represented by the above-mentioned -Funzo (1) are shown in Table 1. In the table, for those in which optical isomers exist, those expressed as (R) or (S) are respectively R
5 bodies, and those not mentioned represent racemic bodies.
本発明の前記−船蔵(I)で表わされるベンゾフラン誘
導体は、例えば下記に示す方法により製造することがで
きるが、これらの方法に限定されるものではない。The benzofuran derivative represented by the above-mentioned (I) of the present invention can be produced, for example, by the method shown below, but is not limited to these methods.
A法
(I[)
(II[)
(I−a)
1式中、
Xはハロゲン原子を表わし、
Yは基
R1は前記−船蔵(I)におけると同じ意味を示す。]
上記−船蔵(I−a)で表わされる本発明化合物は式(
II)で表わされる化合物と式(Ill)で表わされる
化合物とを塩基性物質の存在下に適当な溶媒中で反応さ
せることにより得ることができる。Method A (I[) (II[) (I-a) In formula 1, X represents a halogen atom, and Y is a group R1 has the same meaning as in the above-mentioned -Funazura (I). ] The compound of the present invention represented by the above-Funazura (I-a) has the formula (
It can be obtained by reacting the compound represented by II) with the compound represented by formula (Ill) in a suitable solvent in the presence of a basic substance.
中間体(II)のスルホニルノ・ライドは、それ自体公
知の方法或いはそれに準する製造方法によって得ること
がでさる[例えば(J ournal of theC
he+oical 5ociety、 5eries
C、p 1265 ;(1965年)参照。]
使用される化合物(I[I)は、化合物(I[)に対し
、通常1.0ないし5.0モル倍が適当である。The sulfonylnolide of intermediate (II) can be obtained by a method known per se or a production method analogous thereto [for example, (Journal of the C.
he+oical 5ociety, 5eries
C, p 1265; (1965). ] Compound (I[I) to be used is usually suitably used in an amount of 1.0 to 5.0 times the mole of compound (I[).
溶媒としては、例えば、アセトンなどのケトン類:テト
ラヒドロフラン、ジオキサン、エーテルなどのエーテル
類:酢酸エチルなどのエステルwiニジクロロメタンな
どのハロゲン化炭化水素;ベンゼン、クロロベンゼンな
どの芳香族炭化水素類;ジメチルホルムアミドなどの極
性溶媒などを単狡または混合して使用することができる
。更に、水と前記溶媒類との混合系も実施可能である。Examples of solvents include ketones such as acetone; ethers such as tetrahydrofuran, dioxane, and ether; esters such as ethyl acetate; halogenated hydrocarbons such as dichloromethane; aromatic hydrocarbons such as benzene and chlorobenzene; dimethylformamide. Polar solvents such as, etc. can be used alone or in combination. Furthermore, a mixed system of water and the above-mentioned solvents can also be implemented.
溶媒の使用量には特別な制限はないが、通常、化合物(
II)の量の5ないし20重量倍が適当である。There are no particular restrictions on the amount of solvent used, but it is usually
5 to 20 times by weight the amount of II) is suitable.
塩基性物資としては、例えば、炭酸アルカリ、苛性アル
カリなどの無機物資、トリエチルアミン、ピリジンなど
のアミン類の他、化合物(I[l)自身を塩基性物質と
して使用することもできる。塩基性物質の使用量は、化
合物(It)に対し、通常1゜0ないし5.0モル倍が
適当である。As the basic substance, for example, in addition to inorganic substances such as alkali carbonate and caustic alkali, and amines such as triethylamine and pyridine, the compound (I[l) itself can also be used as the basic substance. The appropriate amount of the basic substance to be used is usually 1.0 to 5.0 times the amount of compound (It) by mole.
反応温度は、水冷下ないし溶媒の沸点の温度範囲で任意
に設定できる。The reaction temperature can be arbitrarily set within the temperature range of water cooling to the boiling point of the solvent.
反応時間は、設定条件によって変化するが通常、lない
し24時間で終了させることができる。Although the reaction time varies depending on the set conditions, the reaction can usually be completed in 1 to 24 hours.
生成物(I−a)は常法により反応混合物から単離でき
、再結晶、カラムクロマトグラフィーなどにより容易に
精製することができる。Product (Ia) can be isolated from the reaction mixture by conventional methods and easily purified by recrystallization, column chromatography, etc.
B法
(IV) (V)
[式中、Zはハロゲン原子を表わし、AがR1を表わす
ときBはR4を表わし、AがR4を表わすときBはR1
を表わし、R1、R1、R3およびR′は前記−船蔵(
1)におけると同じ意味を示す。】上記反応式において
式(1−b)で表わされる本発明化合物は、化合物(I
V)と化合物(V)とを塩基性物質の存在下に適当な溶
媒中で反応させることにより得ることができる。化合物
(rV)は前述のA法あるいは特願平 号
明細書に記載の方法により製造することができる。Method B (IV) (V) [In the formula, Z represents a halogen atom, when A represents R1, B represents R4, and when A represents R4, B represents R1
, and R1, R1, R3 and R' are the above-mentioned - ship warehouse (
It has the same meaning as in 1). ] In the above reaction formula, the compound of the present invention represented by formula (1-b) is compound (I
It can be obtained by reacting V) with compound (V) in an appropriate solvent in the presence of a basic substance. Compound (rV) can be produced by the method A described above or the method described in the specification of the patent application No. 1.
使用される化合物(V)は、化合物(mV)に対し、通
常1.0ないし5.0モル倍が適当である。The amount of compound (V) to be used is usually 1.0 to 5.0 times the amount of compound (mV) by mole.
溶媒としては、例えば、アセトンなどのクトン類;ラト
ラヒドロフラン、ジオキサン、エーテルなどのエーテル
類;酢酸エチルなどのエステル類ニジクロロメタンなど
のハロゲン化炭化水素f:ベンゼン、クロロベンゼンな
どの芳香族炭化水素類;ジメチルホルムアミドなどの極
性溶媒などを単独または混合して使用することができる
。更に、水と前記溶媒類との混合系も実施可能である。Examples of solvents include chthons such as acetone; ethers such as latrahydrofuran, dioxane, and ether; esters such as ethyl acetate; halogenated hydrocarbons such as dichloromethane; and aromatic hydrocarbons such as benzene and chlorobenzene. ; Polar solvents such as dimethylformamide can be used alone or in combination. Furthermore, a mixed system of water and the above-mentioned solvents can also be implemented.
溶媒の使用量には特別な制限はないが、通常、化合物(
IV)の量の5ないし20重量倍が適当である。There are no particular restrictions on the amount of solvent used, but it is usually
5 to 20 times by weight the amount of IV) is suitable.
塩基性物質としては、例えば、炭酸アルカリ、苛性アル
カリなどの無機物質、水素化ナトリウム、水素化カリウ
ムなどの金属水素化物等が使用され、その使用量は、化
合物(mV)に対し、通常1.0ないし5.0モル倍が
適当である。As the basic substance, for example, inorganic substances such as alkali carbonate and caustic alkali, metal hydrides such as sodium hydride and potassium hydride, etc. are used, and the amount used is usually 1. 0 to 5.0 mole times is appropriate.
反応温度は、水冷下ないし溶媒の沸点の温度範囲で任意
に設定できる。The reaction temperature can be arbitrarily set within the temperature range of water cooling to the boiling point of the solvent.
反応時間は、設定条件によって変化するが通常、■ない
し24時間で終了させることができる。The reaction time varies depending on the setting conditions, but usually the reaction can be completed in 2 to 24 hours.
生成物(I−b)は常法により反応混合物から単離でき
、再結晶、カラムクロマトグラフィーなどにより容易に
精製することができる。Product (I-b) can be isolated from the reaction mixture by conventional methods and easily purified by recrystallization, column chromatography, etc.
次に具体例を挙げて、本発明を更に具体的に説明する。Next, the present invention will be explained in more detail by giving specific examples.
実施例 l
スルホンアミド(化合物No、318)の合成:0、N
−ジメチルヒドロキシルアミン塩酸塩2゜6gを水冷下
、30%水酸化ナトリウム水溶液に加え、室温にて1時
間撹拌を続けた。この水溶液をエーテル抽出し、乾燥し
た後、エーテル溶液のまま、3.3−ジメチル−2,3
−ジヒドロベンゾ7ランー5−イルスルホニルクロライ
ド59をテトラヒドロ7ラン5+iQに溶解した溶液に
、水冷下、撹拌しながら滴下した。さらに室温にて12
時間撹拌し、反応液をエーテル抽出し、IN塩酸、飽和
食塩水で順次洗浄した後、乾燥し、溶媒を留去してシリ
カゲルカラムクロマトグラフィーで精製した。目的のN
−メトキシ−N−メチル− (3.3−ジメチル−2.
3−ジヒドロベンゾフラン−5−イル)スルホンアミF
0.35g (収率49%)を得た。Example l Synthesis of sulfonamide (compound No. 318): 0, N
-2.6 g of dimethylhydroxylamine hydrochloride was added to a 30% aqueous sodium hydroxide solution under water cooling, and stirring was continued at room temperature for 1 hour. This aqueous solution was extracted with ether, and after drying, 3.3-dimethyl-2,3
-Dihydrobenzo7rane-5-ylsulfonyl chloride 59 was added dropwise to a solution of tetrahydro7rane 5+iQ with stirring under water cooling. Further at room temperature 12
After stirring for hours, the reaction solution was extracted with ether, washed successively with IN hydrochloric acid and saturated brine, dried, the solvent was distilled off, and the mixture was purified by silica gel column chromatography. Purpose N
-Methoxy-N-methyl- (3.3-dimethyl-2.
3-dihydrobenzofuran-5-yl)sulfonamide F
0.35 g (yield 49%) was obtained.
実施例 2 3。Example 2 3.
3−ジメチル−2。3-dimethyl-2.
3−ジヒドロベンゾ7
ラン−5−イルスルホンアミド1.0g、無水炭酸カリ
ウム0.809にアセトン7WQを添力口し、撹拌下、
室温でアセチルクロライドQ、41+++12を徐々に
加え、13時間還流温度にて撹拌した。3-Dihydrobenzo 7 Acetone 7WQ was added to 1.0 g of ran-5-ylsulfonamide and 0.809 g of anhydrous potassium carbonate, and while stirring,
Acetyl chloride Q, 41+++12 was gradually added at room temperature, and the mixture was stirred at reflux temperature for 13 hours.
反応液を壇酸酸性にし、エーテル抽出し、このエーテル
層を炭酸水素ナトリウム水溶液にて抽出したそ後、この
水層を再び塩r11酸性にしてエーテル抽出した。乾燥
後、溶媒を留去し、目的のN−アセチル−(3,3−ジ
メチル−2,3−ジヒドロベンゾ7ランー5−イル)ス
ルホンアミド0.619 (収率51%)を得た。The reaction solution was made acidic with acidic acid and extracted with ether. The ether layer was extracted with an aqueous solution of sodium bicarbonate, and then the aqueous layer was made acidic with salt r11 again and extracted with ether. After drying, the solvent was distilled off to obtain the target N-acetyl-(3,3-dimethyl-2,3-dihydrobenzo7ran-5-yl)sulfonamide 0.619 (yield 51%).
実施例 3
3.3−ジメチル−2,3−ジヒドロペンツ7ランー5
−イルスルホニルクロライ、ド1.9gをテトラヒドロ
フラン5+e12に溶解し、水冷下、撹拌しながらアニ
リン3.6IIlflを徐々に加え、12時間室温にて
撹拌した。反応液をエーテルにて抽出し、IN塩酸、飽
和食塩水で順次洗浄し!−後、乾燥し、溶媒を留去して
シリカゲルカラムクロマトグラフィーで精製した。目的
のN−フェニル−(3,3−ジメチル−2,3−ジヒド
ロベンゾフラン−5−イル)スルホンアミド1.Og
(収率43%)を得た。Example 3 3.3-dimethyl-2,3-dihydropenz7ran-5
1.9 g of -ylsulfonyl chloride was dissolved in 5+e12 of tetrahydrofuran, and 3.6 IIlf of aniline was gradually added while stirring under water cooling, followed by stirring at room temperature for 12 hours. The reaction solution was extracted with ether and washed successively with IN hydrochloric acid and saturated saline! After drying, the solvent was distilled off and the product was purified by silica gel column chromatography. Desired N-phenyl-(3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)sulfonamide 1. Og
(yield 43%).
実施例 4
60%水素化ナトリウム0.109をジメチルホルムア
ミド5+o12に溶解し、水冷下で撹拌しながら、ジメ
チルホルムアミド5iに溶解したN−メチル−(3,3
−ジメチル−2,3−ジヒドロベンゾフラン−5−イル
)スルホンアミド0゜609を滴下した。次いで、室温
にてブロモ酢酸メチル0.429を徐々に加え、室温の
まま18時間撹拌を続けた。反応液をエーテル抽出し、
水洗した後、乾燥した。溶媒を留去し、シリカゲルクロ
マトグラフィーで精製しt;。目的のN−メトキシカル
ボニルメチル−N−メチル−(3,3−ジメチル−2,
3−ジヒドロベンゾフラン−5−イル)スルホンアミド
0.579 (収率73%)を得た。Example 4 60% sodium hydride 0.109 was dissolved in dimethylformamide 5+o12, and while stirring under water cooling, N-methyl-(3,3
-dimethyl-2,3-dihydrobenzofuran-5-yl)sulfonamide 0°609 was added dropwise. Then, 0.429 g of methyl bromoacetate was gradually added at room temperature, and stirring was continued for 18 hours at room temperature. The reaction solution was extracted with ether,
After washing with water, it was dried. The solvent was distilled off and purified by silica gel chromatography. The desired N-methoxycarbonylmethyl-N-methyl-(3,3-dimethyl-2,
0.579 (yield: 73%) of 3-dihydrobenzofuran-5-yl)sulfonamide was obtained.
実施例 5
N−インプロポキシ−(3,3−ジメチル−23−ジヒ
ドロベンゾフラン−5−イル)スルホンアミド0.50
g、無水炭酸カリウム0.299にジメチルホルホルム
アミド4vaQを添加し、撹拌下、室温で臭化ベンジル
0.369を徐々に加え、12時間室温にて撹拌した。Example 5 N-inpropoxy-(3,3-dimethyl-23-dihydrobenzofuran-5-yl)sulfonamide 0.50
4 vaQ of dimethylformamide was added to 0.299 g of anhydrous potassium carbonate, and while stirring, 0.369 g of benzyl bromide was gradually added at room temperature, and the mixture was stirred at room temperature for 12 hours.
反応液をエーテルにて抽出し、水洗した後、乾燥し、溶
媒を留去してシリカゲルクロマトグラフィーで精製した
。The reaction solution was extracted with ether, washed with water, dried, the solvent was distilled off, and the extract was purified by silica gel chromatography.
目的のN−ベンジル−N−インプロポキシ−(33−ジ
メチル−2,3−ジヒドロベンゾ7ランー5−イル)ス
ルホンアミド0゜
3g
(収率96
%)を得た6
実施例 6
60%水素化ナトリウム0.12gをジメチルホルムア
ミド4raQに溶解し、水冷下で撹拌しながら、ジメチ
ルホルムアミド4tnQに溶解したN−ベンジル−(3
,3−ジメチル−2,3−ジヒドロベンゾ7ランー5−
イル)スルホンアミド0゜909を滴下した。次いで、
室温にてヨウ化メチル0.449を徐々に加え、室温の
まま2時間半撹拌を続けた。反応液をエーテル抽出し、
水洗し、乾燥した後、再結晶により、目的のN−ベンジ
ル−N−メチル−(3,3−ジメチル−2,3−ジヒド
ロベンゾフラン−5−イル)スルホンアミド0.63g
(収率67%)を得た。Example 6 60% hydrogenation 0.3 g (yield 96%) of the desired N-benzyl-N-inpropoxy-(33-dimethyl-2,3-dihydrobenzo7lan-5-yl)sulfonamide was obtained. Dissolve 0.12 g of sodium in dimethylformamide 4raQ, and while stirring under water cooling, dissolve N-benzyl-(3
,3-dimethyl-2,3-dihydrobenzo7ran-5-
0.909 ml of sulfonamide was added dropwise. Then,
0.449 g of methyl iodide was gradually added at room temperature, and stirring was continued for 2.5 hours at room temperature. The reaction solution was extracted with ether,
After washing with water and drying, 0.63 g of the desired N-benzyl-N-methyl-(3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)sulfonamide was obtained by recrystallization.
(yield 67%).
実施例 7
N−(σ−メトキシベンジル)−N−メチルー(3,3
−ジメチル−2,3−ジヒドロベンゾフロ0%水素化ナ
トリウム0.14gをジメチルホルムアミド51に溶解
し、水冷下撹拌しながら、ジメチルホルムアミド5mf
fに溶解したN−メチル−(3,3−ジメチル−2,3
−ジヒドロベンゾフラン−5−イル)スルホンアミド0
.80gを滴下しt;。次いで、室温にてα−メトキシ
ベンジルクロライド0.57gを徐々に加え、室温のま
ま18時間撹拌を続けた0反応液をエーテル抽出し、水
洗し、乾燥した後、溶媒を留去してシリカゲルカラムク
ロマトグラフィーで精製した。Example 7 N-(σ-methoxybenzyl)-N-methyl-(3,3
-Dimethyl-2,3-dihydrobenzofuro 0% sodium hydride 0.14g was dissolved in dimethylformamide 51, and while stirring under water cooling, dimethylformamide 5mf was added.
N-methyl-(3,3-dimethyl-2,3
-dihydrobenzofuran-5-yl)sulfonamide 0
.. Drop 80g. Next, 0.57 g of α-methoxybenzyl chloride was gradually added at room temperature, and stirring was continued for 18 hours at room temperature.The reaction solution was extracted with ether, washed with water, dried, and the solvent was distilled off. Purified by chromatography.
目的のN−(σ−メトキシベンジル)−N−メチル−(
3,3−ジメチル−2,3−ジヒドロベンゾ7ランー5
−イル)スルホンアミド1.059(収率88%)を得
た。The desired N-(σ-methoxybenzyl)-N-methyl-(
3,3-dimethyl-2,3-dihydrobenzo7lane-5
-yl) sulfonamide 1.059 (yield 88%) was obtained.
同様の方法により下記衣2記載の化合物を合成した。そ
れらの化合物のNMRデータを下記衣2に示す。A compound described in Cloth 2 below was synthesized in a similar manner. NMR data of those compounds are shown in Figure 2 below.
表
本発明の除草剤は、前記−船蔵(1)の新規ベンゾフラ
ン誘導体を有効成分として含有している。Table: The herbicide of the present invention contains the above-mentioned novel benzofuran derivative (1) as an active ingredient.
本発明の前記化合物を除草剤として用いる場合には、農
薬の調製に一般的に使用される担体もしくは希釈剤、添
加剤及び補助剤等とそれ自体公知の手法で混合して、通
常農薬として用いられる製剤形態、例えば粉剤、粒剤、
水和剤、札割、水溶剤、フロアブル剤等に調製して使用
される。また他の農薬、例えば殺菌剤、殺虫剤、殺ダニ
剤、他の除草剤、植物生長調節剤及び肥料、土壌改良剤
等と混合または併用して使用することができる。When the compound of the present invention is used as a herbicide, it is mixed with carriers, diluents, additives, auxiliaries, etc. commonly used in the preparation of agricultural chemicals by a method known per se. formulations such as powders, granules,
It is prepared and used in hydrating powders, bill splitters, water solvents, flowable agents, etc. It can also be mixed or used in combination with other agricultural chemicals, such as fungicides, insecticides, acaricides, other herbicides, plant growth regulators, fertilizers, soil conditioners, and the like.
特に他の除草剤と混合使用することにより、使用薬量を
減少させ、また省力化をもたらすのみならず、両薬剤の
共力作用による殺草ス”ペクトラムの拡大並びに相乗作
用による一層高い効果も期待できる。In particular, when used in combination with other herbicides, it not only reduces the amount of chemicals used and saves labor, but also expands the herbicidal spectrum due to the synergistic action of both herbicides, and increases the effectiveness due to the synergistic action. You can expect it.
製剤に際して用いられる担体若くは希釈剤としては、一
般に農業上使用される固体ないしは液体の担体が用いら
れる。固体担体としてはカオリナイト群、モンモリロナ
イト群あるいはアバタルジャイト群等で代表されるクレ
ー類やタルク、雲母、ロウ石、軽石、バーミキュライト
、石膏、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、りん久方、ゼオライト、無水ケイ酸、
合成ケイ酸力ルンウム等の無機物質;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
ッド樹脂、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、フーバルガム、ダンマル
ガム等の合成または天然の高分子化合物;そのほかカル
ナバロウ、蜜ロウ等のワックス類あるいは尿素等が例示
できる。As the carrier or diluent used in formulation, solid or liquid carriers commonly used in agriculture are used. Solid carriers include clays represented by the kaolinite group, montmorillonite group, or abatalgite group, talc, mica, waxite, pumice, vermiculite, gypsum, calcium carbonate, dolomite, diatomaceous earth, magnesium lime, and phosphorus. , zeolite, silicic anhydride,
Inorganic substances such as synthetic silicate; organic substances such as soybean flour, tobacco powder, walnut flour, wheat flour, wood flour, starch, crystalline cellulose; coumaron resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene Synthetic or natural polymer compounds such as glycol, ketone resin, ester gum, fuval gum, and dammar gum; other examples include waxes such as carnauba wax and beeswax, and urea.
適当な液体年休としては、例えば、ケロシン、鉱油、ス
ピンドル油、ホワイトオイル等のパラフィン系もしくは
ナフテン系炭化水素;トルエン、キシレン、エチルベン
ゼン、クメン、メチルナフタレン等の芳香族炭化水素二
ジオキサン、テトラヒドロ7ラン等のエーテル類: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、アセトフェノン、インホロン等のケトン
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、エチレンクリコールフェニルエーテル、ジエチレン
グリコールエチルエーテル、ジエチレングリコールブチ
ルエーテル等のエーテルアルコール類;ジメチルホルム
アミド、ジメチルスルホキシド等の極性溶媒あるいは水
等が挙げられる。Suitable liquid annual leave includes, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, white oil; aromatic hydrocarbons such as toluene, xylene, ethylbenzene, cumene, methylnaphthalene, didioxane, tetrahydro7 Ethers such as oran: Ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, inholone; Esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate, etc.: methanol, Alcohols such as n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, benzyl alcohol; Ether alcohols such as ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether; polarity such as dimethylformamide, dimethyl sulfoxide, etc. Examples include a solvent or water.
その他に本発明の化合物の乳化、分散、湿潤、拡展、結
合、崩解性調節、有効成分安定化、流動性改良、防錆等
の目的で界面活性剤その他の補助剤を使用することもで
きる。使用される界面活性剤の例としては、非イオン性
、陰イオン性、陽イオン性及び両性イオン性のいずれの
化合物も使用しうるが、通常は非イオン性及び(又は)
陰イオン性の化合物が使用される。適当な非イオン性界
面活性剤としては、例えば、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化合物、イン
オクチルフェノール、ノニルフェノール等のアルキルフ
ェノールにエチレンオキシドを重合付加させた化合物、
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化合物、ソルビタ
ン等の多価アルコールの高級脂肪酸エステル及びそれに
エチレンオキシドを重合付加させた化合物及びエチレン
オキシドとプロピレンオキシドを重合付加させた化合物
等が挙げられる。In addition, surfactants and other auxiliary agents may be used for the purposes of emulsifying, dispersing, wetting, spreading, binding, adjusting disintegration, stabilizing active ingredients, improving fluidity, and preventing rust of the compound of the present invention. can. Examples of surfactants used include nonionic, anionic, cationic, and zwitterionic compounds, but typically nonionic and/or
Anionic compounds are used. Suitable nonionic surfactants include, for example, compounds in which ethylene oxide is polymerized and added to higher alcohols such as lauryl alcohol, stearyl alcohol, and oleyl alcohol; compounds in which ethylene oxide is polymerized and added to alkyl phenols such as inoctylphenol and nonylphenol;
Compounds obtained by polymerizing and adding ethylene oxide to alkylnaphthols such as butylnaphthol and octylnaphthol, compounds obtained by polymerizing and adding ethylene oxide to higher fatty acids such as palmitic acid, stearic acid, and oleic acid, higher fatty acid esters of polyhydric alcohols such as sorbitan, and Examples thereof include a compound obtained by polymerizing and adding ethylene oxide and a compound obtained by polymerizing and adding ethylene oxide and propylene oxide.
適当な陰イオン性界面活性剤としては、例えば、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i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挙げられる。Suitable anionic surfactants include, for example, sodium lauryl sulfate, alkyl acid ester salts such as oleyl alcohol sulfate amine salts, alkyl sulfonic acids such as sodium sulfosuccinate dioctyl ester, and sodium 2-ethylhexene sulfonate. Salts include arylsulfonates such as sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, sodium ligninsulfonate, and sodium dodecylbenzenesulfonate.
更に本発明の除草剤には製剤の性状を改善し、除草効果
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
用することもでさる。Furthermore, the herbicide of the present invention may contain polymeric compounds such as casein, gelatin, albumin, glue, sodium alginate, carboxymethylcellulose, methylcellulose, hydroxyethylcellulose, polyvinyl alcohol, etc., in order to improve the properties of the preparation and increase the herbicidal effect. It is also possible to use adjuvants.
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本独あるいは組み
合わせて適宜使用される。The above-mentioned carriers and various auxiliary agents are used individually or in combination as appropriate depending on the purpose, taking into account the dosage form of the preparation, the application situation, etc.
このようにして得られた各種製剤形における本発明化合
物(有効成分)含有率は製剤形により種々変化するもの
であるが、通常0.1〜99重量%が適当であり、とり
わけ1〜8011量%が最も好ましい。The content of the compound of the present invention (active ingredient) in the various formulations thus obtained varies depending on the formulation, but it is usually appropriate to range from 0.1 to 99% by weight, especially from 1 to 8011% by weight. % is most preferred.
粉剤の場合は、たとえば有効成分化合物を通常1〜25
重量%含有し、残部は固体担体である。In the case of powders, for example, the active ingredient compound is usually 1 to 25
% by weight, the remainder being solid carrier.
水利剤の場合は、たとえば有効成分化合物を通常25〜
90重量%含有し、残部は固体担体、分散湿潤剤であっ
て、必要に応じて保護コロイド剤、消泡剤等が加えられ
る。In the case of irrigation agents, for example, the active ingredient compound is usually 25 to
The content is 90% by weight, and the remainder is a solid carrier, a dispersion wetting agent, and a protective colloid agent, an antifoaming agent, etc. are added as necessary.
粒剤の場合は、たとえば有効成分化合物を通常1〜35
重量%含有し、残部は大部分が固体担体及び界面活性剤
等である。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1.5mI
!+である。In the case of granules, for example, the active ingredient compound is usually 1 to 35
% by weight, and the remainder consists mostly of solid carriers, surfactants, etc. 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 1.5 mI.
! It is +.
乳剤の場合は、たとえば有効成分化合物を通常5〜30
重量%含有しており、これに約5ないし20重量%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。In the case of emulsions, for example, the active ingredient compound is usually 5 to 30
This includes approximately 5 to 20% by weight of emulsifier, the remainder being a liquid carrier, and a rust inhibitor added as needed.
70アブル剤の場合は、例えば有効成分化合物を通常5
〜50%含有しており、これに3ないし10重量%の分
散1liij!!S剤が含まれ残部は水であり必要に応
じて保護コロイド剤、防腐剤、消泡剤等が加えられる。For example, in the case of a 70-tablet drug, the active ingredient compound is usually 5%
~50%, with a dispersion of 3 to 10% by weight! ! The S agent is contained and the remainder is water, and a protective colloid agent, preservative, antifoaming agent, etc. are added as necessary.
本発明の新規なベンゾフラン誘導体は、−数式(I)の
化合物のままあるいは上述した様な任意の調製形態で施
用することができる。The novel benzofuran derivatives of the invention can be applied as compounds of the formula (I) or in any preparation form as described above.
本発明の除草剤は、水田および畑地に生育する発生前か
ら生育期までの諸雑草の駆除または防除に施用できる。The herbicide of the present invention can be applied to exterminate or control various weeds growing in rice fields and fields from before emergence to the growing season.
その施用量は一般式(1)で表わされる化合物量(有効
成分量)としてIha当り、0.01〜5kg程度、好
ましくは0−1−1kg程度であり、目的とする雑草の
種類、生育段階、施用場所、施用時期、天候等によって
適宜に選択変更できる。The application amount is about 0.01 to 5 kg, preferably about 0-1-1 kg, per Iha as the amount of the compound represented by general formula (1) (active ingredient amount), and the amount of the compound expressed by general formula (1) is about 0.01 to 5 kg, preferably about 0-1 to 1 kg. , the selection can be changed as appropriate depending on the application location, application time, weather, etc.
次に、本発明の化合物を用い9た製剤例の数態様を示す
。下記製剤例中の「部」は重量基準である。Next, several embodiments of formulation examples using the compound of the present invention will be shown. "Parts" in the following formulation examples are based on weight.
製剤例1(粒剤)
化合物No、14 5部ベントナイト
50部タルク
40部ドデシルベンゼン
スルホン酸ソーダ 2部
リグニンスルホン酸ソーダ 2部
ポリオキシエチレンスチリル
フェニルエーテル 1部
以上を充分に混合した後、適量の水を加えて混練し、造
粒機用いて造粒して粒剤100部を得た。Formulation example 1 (granules) Compound No. 14 5 parts bentonite
50 parts talc
40 parts Sodium dodecylbenzenesulfonate 2 parts Sodium ligninsulfonate 2 parts Polyoxyethylene styrylphenyl ether After thoroughly mixing 1 part or more, add an appropriate amount of water, knead, and granulate using a granulator. 100 parts of the agent were obtained.
製剤例2(水利剤)
化合物No、7Q 20部ケイソウ土
60部
ホワイトカーボン 15部
リグニンスルホン酸ソーダ 3部
Ffシルベンゼンスルホン酸
ソーダ 2部
以上を混合し、ニーダ−で均一に混合粉砕して水利剤1
00部を得た。Formulation Example 2 (Irrigation agent) Compound No. 7Q 20 parts diatomaceous earth
60 parts White carbon 15 parts Sodium lignin sulfonate 3 parts Ff Sodium sylbenzene sulfonate Mix 2 or more parts and mix and crush them uniformly in a kneader to obtain irrigation agent 1.
I got 00 copies.
製剤例3(乳剤)
化合物Noニア5 30部キシレン
55部
シクロヘキサノン 10部
ドデシルベンゼン
スルホン酸カルシウム 3部
ポリオキシエチレン
スチリルフェニルニーf ル2部
以上を均一に混合溶解して乳剤100部を得I―。Formulation example 3 (emulsion) Compound Nonia 5 30 parts xylene
55 parts cyclohexanone 10 parts Calcium dodecylbenzenesulfonate 3 parts Polyoxyethylene styrylphenyl needle 2 or more parts were uniformly mixed and dissolved to obtain 100 parts of emulsion I-.
上述の製剤例に準じて本発明の化合物を用いた薬剤がそ
れぞれ製剤できた。Drugs using the compounds of the present invention were prepared according to the above-mentioned formulation examples.
(発明の効果)
本発明の上記−数式(りで表わされるベンゾフラン訴導
体は、文献未記載の新規な化合物である。この上記−数
式(1)で表わされる化合物は、ベンゾフラン骨格の5
位にスルホンアミドが結合しt;構造をとっていること
が特徴であり1、°その構造的特徴によって、優れた除
草効果が発現するものと考えられる。(Effects of the Invention) The benzofuran compound represented by the above-mentioned formula (RI) of the present invention is a novel compound that has not been described in any literature.
It is characterized by having a structure in which a sulfonamide is bonded to the 1,° position, and it is thought that this structural feature provides excellent herbicidal effects.
本発明の化合物及び除草剤は農耕地に生育する発生前か
ら生育期までの諸雑草を防除でさる1例えば、ノビエ、
ホタルイ、マツバイ、ミズガヤツリ、コウキャガラ、ク
ログワイ、シズイ等の水田雑草や、メヒシバ、エノコロ
グサ、オヒシシバ、スズメツヒエ、スズメノテッポウ、
ヒス類等の畑地雑草を防除できる。更に、水田、畑地の
みならず、果樹園、桑畑、芝生、非農耕地においても試
用することができる。The compounds and herbicides of the present invention can control various weeds growing in agricultural land from the pre-emergence stage to the growing season.
Paddy field weeds such as bulrush, Japanese cypress, Japanese cypress, black chickadee, black bream, and staghorn;
Can control field weeds such as hissies. Furthermore, it can be used not only in rice paddies and fields, but also in orchards, mulberry fields, lawns, and non-agricultural lands.
しかも、本発明化合物は栽培作物に選択性を有し、特に
、イネに対する安全性が極めて高く、水田に発生する諸
雑草を有効に防除することがら、優れた水田用除草剤と
しての効果が期待できる。Moreover, the compound of the present invention has selectivity to cultivated crops, is particularly safe for rice, and effectively controls various weeds that occur in rice fields, so it is expected to be effective as an excellent herbicide for rice fields. can.
次に本発明除草剤の効果を試験例をあげて説明する。Next, the effect of the herbicide of the present invention will be explained by giving test examples.
試験例 l(水田土壌処理)
面積200ca’のプラスチックポットに適量の化成肥
料を混合した水田土壌を詰め、これに予め温室内で生育
させた2葉期の水稲(品種:コシヒカリ)を3株(2本
1株)移植し、更にノビエ、ホタルイの種子と、ミズガ
ヤツリ及びクログワイの塊茎を播種した。Test Example l (Paddy soil treatment) A plastic pot with an area of 200 ca' was filled with paddy soil mixed with an appropriate amount of chemical fertilizer, and three plants of paddy rice (variety: Koshihikari) at the two-leaf stage that had been grown in a greenhouse in advance ( Two plants (one plant) were transplanted, and seeds of Japanese wildflower and firefly, as well as tubers of Japanese cypress and Japanese cypress were sown.
水稲移植及び雑草播種3日後に、表3に示す各化合物を
製剤例2に準じて水利剤に調整し、有効成分でlha当
り0−5kgとなるように適量の水で希釈し、ピペット
で滴下処理した。除草効果及び薬害程度の調査は、薬剤
処理30日後に次の基準に従い行った。Three days after paddy rice transplantation and weed sowing, each compound shown in Table 3 was prepared as an irrigation agent according to Formulation Example 2, diluted with an appropriate amount of water to give an active ingredient of 0-5 kg per lha, and dripped with a pipette. Processed. The herbicidal effect and the degree of chemical damage were investigated 30 days after the chemical treatment according to the following criteria.
その結果を表3に示す。The results are shown in Table 3.
除草効果 浅草率(無九理区に対す浅草率)10
0% 〜 1%未満
9 1%以上〜 lO%//
8 11%〃〜 20%!/
21 %
31%
41 %
51%
61%
71%
81%
91%
〜 30%
〜 40%
〜 50%
〜 60%
〜 70%
〜 80%
〜 90%
〜100%
完全枯死
90%〜99%抑制
80%〜89%
70%〜79%
60%〜69%
50%〜59%
40%〜49%
30%〜39%
20%〜29%
10%〜19%
0%〜 9%
表
表
(つづき)
表
(つづき)
比較化合物Aは下記の化合物を表す。(以下の表におい
ても同様)
(特開昭55−20788号公報参照)試験例 2(水
田生育期処理)
面積200ca+”のプラスチックポットに適量の化成
肥料を混合した水田土壌を詰め、これに予め温室内で生
育させた2葉期の水稲(品種:コシヒカリ)を3株(2
本1株)移植し、更にノビエ、ホタルイの種子と、ミズ
ガヤツリ及びクログワイの塊茎を播種した。Weeding effect Asakusa rate (Asakusa rate for Mukuri area) 10
0% ~ less than 1% 9 1% or more ~ lO% // 8 11% ~ 20%! / 21% 31% 41% 51% 61% 71% 81% 91% ~ 30% ~ 40% ~ 50% ~ 60% ~ 70% ~ 80% ~ 90% ~ 100% Complete suppression of death by 90% ~ 99% 80 %~89% 70%~79% 60%~69% 50%~59% 40%~49% 30%~39% 20%~29% 10%~19% 0%~9% Table (continued) Table (continued) Comparative compound A represents the following compound. (The same applies to the table below) (Refer to Japanese Unexamined Patent Publication No. 55-20788) Test Example 2 (Paddy growing season treatment) A plastic pot with an area of 200 ca+" was filled with paddy soil mixed with an appropriate amount of chemical fertilizer, and the soil was preliminarily poured into the pot. Three plants (2
This 1st plant) was transplanted, and seeds of Japanese wildflower and firefly, and tubers of Japanese cypress and Japanese cypress were sown.
水稲移植及び雑草播種10日後に、表4に示す各化合物
を製剤例2に準じて水利剤に調整し、有効成分でlha
当り0.5kg又は1.okgとなるように適量の水で
希釈し、ピペットで滴下処理した。除草効果及び薬害程
度の調査は、薬剤処理30日後に次の基準に従い行った
。Ten days after transplanting paddy rice and sowing weeds, each compound shown in Table 4 was adjusted to an irrigation agent according to Formulation Example 2, and lha
0.5kg or 1. The solution was diluted with an appropriate amount of water to give a solution of 1.0 kg, and added dropwise with a pipette. The herbicidal effect and the degree of chemical damage were investigated 30 days after the chemical treatment according to the following criteria.
その結果を表4に示す。The results are shown in Table 4.
表 4 表 (つづき) (つづき)Table 4 table (continued) (continued)
Claims (2)
原子または低級アルキル基を表わし、R^3は水素原子
、低級アルキル基、低級ハロアルキル基、低級シアノア
ルキル基、低級アルケニル基、低級アルキニル基、置換
されてもよいアリール基または置換されてもよいアラル
キル基を表わし、R^4はヒドロキシ基、低級ハロアル
キル基、低級シアノアルキル基、低級アルケニル基、低
級アルキニル基、置換されてもよいアリール基、置換さ
れてもよいアラルキル基、低級アルコキシ基、置換され
てもよいアリールオキシ基、置換されてもよいアラルキ
ルオキシ基、アルコキシアルキル基、置換されてもよい
アリールオキシアルキル基、置換されてもよいアラルキ
ルオキシアルキル基、アルキルカルボニル基、置換され
てもよいアリールカルボニル基、置換されてもよいアラ
ルキルカルボニル基、アルキルカルボニルアルキル基、
置換されてもよいアリールカルボニルアルキル基、置換
されてもよいアラルキルカルボニルアルキル基、アルコ
キシカルボニル基、置換されてもよいアリールオキシカ
ルボニル基、置換されてもよいアラルキルオキシカルボ
ニル基、アルコキシカルボニルアルキル基、置換されて
もよいアリールオキシカルボニルアルキル基、置換され
てもよいアラルキルオキシカルボニルアルキル基または
アルコキシカルボニルアルコキシ基を表わす。]で表わ
される新規ベンゾフラン誘導体。(1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R^1 and R^2 may be the same or different and represent a hydrogen atom or a lower alkyl group, 3 represents a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower cyanoalkyl group, a lower alkenyl group, a lower alkynyl group, an optionally substituted aryl group, or an optionally substituted aralkyl group, and R^4 is a hydroxy group , lower haloalkyl group, lower cyanoalkyl group, lower alkenyl group, lower alkynyl group, optionally substituted aryl group, optionally substituted aralkyl group, lower alkoxy group, optionally substituted aryloxy group, substituted optional aralkyloxy group, alkoxyalkyl group, optionally substituted aryloxyalkyl group, optionally substituted aralkyloxyalkyl group, alkylcarbonyl group, optionally substituted arylcarbonyl group, optionally substituted aralkylcarbonyl group, alkylcarbonylalkyl group,
Optionally substituted arylcarbonylalkyl group, optionally substituted aralkylcarbonylalkyl group, alkoxycarbonyl group, optionally substituted aryloxycarbonyl group, optionally substituted aralkyloxycarbonyl group, alkoxycarbonylalkyl group, substituted represents an optionally substituted aryloxycarbonylalkyl group, an optionally substituted aralkyloxycarbonylalkyl group, or an optionally substituted alkoxycarbonylalkoxy group. ] A novel benzofuran derivative represented by.
原子または低級アルキル基を表わし、R^3は水素原子
、低級アルキル基、低級ハロアルキル基、低級シアノア
ルキル基、低級アルケニル基、低級アルキニル基、置換
されてもよいアリール基または置換されてもよいアラル
キル基を表わし、R^4はヒドロキシ基、低級ハロアル
キル基、低級シアノアルキル基、低級アルケニル基、低
級アルキニル基、置換されてもよいアリール基、置換さ
れてもよいアラルキル基、低級アルコキシ基、置換され
てもよいアリールオキシ基、置換されてもよいアラルキ
ルオキシ基、アルコキシアルキル基、置換されてもよい
アリールオキシアルキル基、置換されてもよいアラルキ
ルオキシアルキル基、アルキルカルボニル基、置換され
てもよいアリールカルボニル基、置換されてもよいアラ
ルキルカルボニル基、アルキルカルボニルアルキル基、
置換されてもよいアリールカルボニルアルキル基、置換
されてもよいアラルキルカルボニルアルキル基、アルコ
キシカルボニル基、置換されてもよいアリールオキシカ
ルボニル基、置換されてもよいアラルキルオキシカルボ
ニル基、アルコキシカルボニルアルキル基、置換されて
もよいアリールオキシカルボニルアルキル基、置換され
てもよいアラルキルオキシカルボニルアルキル基または
アルコキシカルボニルアルコキシ基を表わす。]で表わ
される、ベンゾフラン誘導体を有効成分として含有する
ことを特徴とする除草剤。(2) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R^1 and R^2 may be the same or different and represent a hydrogen atom or a lower alkyl group, and R^ 3 represents a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower cyanoalkyl group, a lower alkenyl group, a lower alkynyl group, an optionally substituted aryl group, or an optionally substituted aralkyl group, and R^4 is a hydroxy group , lower haloalkyl group, lower cyanoalkyl group, lower alkenyl group, lower alkynyl group, optionally substituted aryl group, optionally substituted aralkyl group, lower alkoxy group, optionally substituted aryloxy group, substituted optional aralkyloxy group, alkoxyalkyl group, optionally substituted aryloxyalkyl group, optionally substituted aralkyloxyalkyl group, alkylcarbonyl group, optionally substituted arylcarbonyl group, optionally substituted aralkylcarbonyl group, alkylcarbonylalkyl group,
Optionally substituted arylcarbonylalkyl group, optionally substituted aralkylcarbonylalkyl group, alkoxycarbonyl group, optionally substituted aryloxycarbonyl group, optionally substituted aralkyloxycarbonyl group, alkoxycarbonylalkyl group, substituted represents an optionally substituted aryloxycarbonylalkyl group, an optionally substituted aralkyloxycarbonylalkyl group, or an optionally substituted alkoxycarbonylalkoxy group. ] A herbicide characterized by containing a benzofuran derivative as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15391090A JPH0446169A (en) | 1990-06-14 | 1990-06-14 | New benzofuran derivative and herbicide containing same derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15391090A JPH0446169A (en) | 1990-06-14 | 1990-06-14 | New benzofuran derivative and herbicide containing same derivative |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0446169A true JPH0446169A (en) | 1992-02-17 |
Family
ID=15572780
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP15391090A Pending JPH0446169A (en) | 1990-06-14 | 1990-06-14 | New benzofuran derivative and herbicide containing same derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0446169A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015096525A (en) * | 2006-03-17 | 2015-05-21 | ザ ジョンズ ホプキンス ユニバーシティ | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
WO2016097394A1 (en) * | 2014-12-19 | 2016-06-23 | Galderma Research & Development | Bicyclic sulfonamide derivatives as inverse agonists of retinoid-related orphan receptor gamma (ror gamma (t)) |
US9617208B2 (en) | 2007-09-26 | 2017-04-11 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
US9932303B2 (en) | 2014-01-17 | 2018-04-03 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxymethanesulfonamide nitroxyl donors |
-
1990
- 1990-06-14 JP JP15391090A patent/JPH0446169A/en active Pending
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015096525A (en) * | 2006-03-17 | 2015-05-21 | ザ ジョンズ ホプキンス ユニバーシティ | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
US9487498B2 (en) | 2006-03-17 | 2016-11-08 | The Johns Hopkins University | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
US9725410B2 (en) | 2006-03-17 | 2017-08-08 | The Johns Hopkins University | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
US9969684B2 (en) | 2006-03-17 | 2018-05-15 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
US10179765B2 (en) | 2006-03-17 | 2019-01-15 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
US10487049B2 (en) | 2006-03-17 | 2019-11-26 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
US10829445B2 (en) | 2006-03-17 | 2020-11-10 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
US11306056B2 (en) | 2006-03-17 | 2022-04-19 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
US9617208B2 (en) | 2007-09-26 | 2017-04-11 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
US9932303B2 (en) | 2014-01-17 | 2018-04-03 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxymethanesulfonamide nitroxyl donors |
WO2016097394A1 (en) * | 2014-12-19 | 2016-06-23 | Galderma Research & Development | Bicyclic sulfonamide derivatives as inverse agonists of retinoid-related orphan receptor gamma (ror gamma (t)) |
FR3030517A1 (en) * | 2014-12-19 | 2016-06-24 | Galderma Res & Dev | BICYCLIC SULFONAMIDE DERIVATIVES AS REVERSE AGONISTS OF GAMMA RETINOID-ASSOCIATED GAMMA ORPHAN RECEPTOR (T) |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH0446169A (en) | New benzofuran derivative and herbicide containing same derivative | |
JPS60156601A (en) | Herbicide for paddy field | |
JPS6116246B2 (en) | ||
JPS6116247B2 (en) | ||
JPH0446168A (en) | New benzofuran derivative and herbicide containing same derivative | |
JPH045282A (en) | New 2-hydrazinobenzothiazole derivative and herbicide comprising the same derivative as active ingredient | |
JPH04145070A (en) | Azidomethylquinoline derivative and herbicide containing the same as active ingredient | |
JP3085412B2 (en) | 1,3,4-thiadiazole derivatives, their production and herbicides | |
JPH0232080A (en) | Pyrano or thiopyrano(4,3-c)pyrazole derivative and herbicide containing said derivative as active ingredient | |
JPH02178266A (en) | Nicotinic acid anilide compound and herbicide containing the compound | |
JPH02142774A (en) | 2-(4-substituted phenyl) imidazolinones, production thereof and herbicide containing the same imidazolinones as active ingredient | |
JPH0446170A (en) | New benzofuran derivative and herbicide containing same derivative | |
JPH045279A (en) | New oxime ether derivative and herbicide and agricultural and horticultural fungicide comprising the same derivative as active ingredient | |
JPH0418070A (en) | Tetrahydrophtalimide derivative and herbicide with the same as active ingredient | |
JPH0429980A (en) | Arylpropionic acid derivative and herbicide | |
JPH03287579A (en) | Novel phenoxypropionic acid derivative and plant growth regulator with the same as active ingredient | |
JPH0532641A (en) | Mercaptotriazine derivative and herbicide containing the same as active ingredient | |
JPH0588225B2 (en) | ||
JPH01180869A (en) | Cyclohexane derivative, its production, herbicide containing it, and method combating weeds using it | |
JPS61145105A (en) | Herbicide composition | |
JPH0466578A (en) | 5-substituted-2,4-diphenylpyrimidine derivative and herbicide comprising the same derivative as active ingredient | |
JPH054973A (en) | 2-pyrimidinyloxyurea derivative and herbicide containing the derivative as active component | |
JPH0477475A (en) | New cyclohexenyloxypyrimidine derivative and herbicide containing the same as active ingredient | |
JPH06329690A (en) | Pyrimidine derivative and herbicide comprising the same as active ingredient | |
JPH0366656A (en) | 1,3,4-oxadiazol-2-(thi)one derivative and herbicide containing the same as active ingredient |