JPH0257543B2 - - Google Patents
Info
- Publication number
- JPH0257543B2 JPH0257543B2 JP56199847A JP19984781A JPH0257543B2 JP H0257543 B2 JPH0257543 B2 JP H0257543B2 JP 56199847 A JP56199847 A JP 56199847A JP 19984781 A JP19984781 A JP 19984781A JP H0257543 B2 JPH0257543 B2 JP H0257543B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- groups
- represented
- alkyl group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 239000004009 herbicide Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- SPAMRUYRVYMHPV-UHFFFAOYSA-N 3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical class C1=CCCC2C(=O)NC(=O)C21 SPAMRUYRVYMHPV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 30
- 239000000203 mixture Substances 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 19
- 230000002363 herbicidal effect Effects 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- -1 tricrene Substances 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000002689 soil Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 description 3
- AFJWMGOTLUUGHF-UHFFFAOYSA-N 4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1CCCC2=C1C(=O)NC2=O AFJWMGOTLUUGHF-UHFFFAOYSA-N 0.000 description 3
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 240000001341 Reynoutria japonica Species 0.000 description 3
- 235000018167 Reynoutria japonica Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-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
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 244000178993 Brassica juncea Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000217446 Calystegia sepium Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 240000003176 Digitaria ciliaris Species 0.000 description 2
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 2
- 235000005476 Digitaria cruciata Nutrition 0.000 description 2
- 235000006830 Digitaria didactyla Nutrition 0.000 description 2
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 240000003173 Drymaria cordata Species 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 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
- 240000007218 Ipomoea hederacea Species 0.000 description 2
- 241000254158 Lampyridae Species 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 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
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 241001233957 eudicotyledons Species 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000004720 fertilization Effects 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- HMXIYEFOOMZRBQ-UHFFFAOYSA-N n-butan-2-yl-2-[3-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-4-fluoroanilino]propanamide Chemical class CCC(C)NC(=O)C(C)NC1=CC=C(F)C(N2C(C3=C(CCCC3)C2=O)=O)=C1 HMXIYEFOOMZRBQ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229960003975 potassium Drugs 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
- 235000007715 potassium iodide Nutrition 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- MFEVGQHCNVXMER-UHFFFAOYSA-L 1,3,2$l^{2}-dioxaplumbetan-4-one Chemical compound [Pb+2].[O-]C([O-])=O MFEVGQHCNVXMER-UHFFFAOYSA-L 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 1
- ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 description 1
- LGTLSVHXYXZUJP-UHFFFAOYSA-N 2-[4-chloro-3-(propylamino)phenyl]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Cl)C(NCCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 LGTLSVHXYXZUJP-UHFFFAOYSA-N 0.000 description 1
- HWSUMDDSUWWNOP-UHFFFAOYSA-N 2-bromo-n-(2-methylbutyl)butanamide Chemical compound CCC(C)CNC(=O)C(Br)CC HWSUMDDSUWWNOP-UHFFFAOYSA-N 0.000 description 1
- HFJATYJXQDZHGW-UHFFFAOYSA-N 2-bromo-n-butan-2-ylpropanamide Chemical compound CCC(C)NC(=O)C(C)Br HFJATYJXQDZHGW-UHFFFAOYSA-N 0.000 description 1
- INQYNAYJCVFXOC-UHFFFAOYSA-N 2-bromo-n-heptan-2-ylpropanamide Chemical compound CCCCCC(C)NC(=O)C(C)Br INQYNAYJCVFXOC-UHFFFAOYSA-N 0.000 description 1
- NGGMOPBLOCRQGW-UHFFFAOYSA-N 2-chloro-2-ethyl-n-phenylbutanamide Chemical compound CCC(Cl)(CC)C(=O)NC1=CC=CC=C1 NGGMOPBLOCRQGW-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZWUBBMDHSZDNTA-UHFFFAOYSA-N 4-Chloro-meta-phenylenediamine Chemical compound NC1=CC=C(Cl)C(N)=C1 ZWUBBMDHSZDNTA-UHFFFAOYSA-N 0.000 description 1
- LLIOADBCFIXIEU-UHFFFAOYSA-N 4-fluoro-3-nitroaniline Chemical compound NC1=CC=C(F)C([N+]([O-])=O)=C1 LLIOADBCFIXIEU-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 1
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 235000006463 Brassica alba Nutrition 0.000 description 1
- 235000011371 Brassica hirta Nutrition 0.000 description 1
- 235000011292 Brassica rapa Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 240000003538 Chamaemelum nobile Species 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001517923 Douglasiidae Species 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- 241000428981 Dyssodia Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- 241001473475 Eutrochium fistulosum Species 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 241001473402 Hieracium Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910000003 Lead carbonate Inorganic materials 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000878007 Miscanthus Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 235000005205 Pinus Nutrition 0.000 description 1
- 241000218602 Pinus <genus> Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 235000003484 annual ragweed Nutrition 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 235000006263 bur ragweed Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000003488 common ragweed Nutrition 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- ORSIRXYHFPHWTN-UHFFFAOYSA-N ethyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC ORSIRXYHFPHWTN-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- SHQJHXLWZDMQEJ-UHFFFAOYSA-N n-methoxy-n-methylcarbamoyl chloride Chemical compound CON(C)C(Cl)=O SHQJHXLWZDMQEJ-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000002364 soil amendment Substances 0.000 description 1
- 239000002881 soil fertilizer Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は新規なテトラヒドロフタルイミド類お
よびこれを有効成分とする除草剤に関する。
従来、Ｎ−アリール−３，４，５，６−テトラ
ヒドロフタルイミド類は優れた除草活性を有する
ことが知られているが、これらの構造の僅かな改
変（置換基の種類、数、位置など）により除草活
性の有無あるいは強弱あるいは選択性などが著し
く異なる場合が多く、単なる化学構造的類似性か
ら新たな化合物の殺草活性あるいは選択性を予知
することは困難である。
本発明者らは、より優れた除草活性と作物安全
性とを有するテトラヒドロフタルイミド類を提供
すべく鋭意研究した結果、Ｎ−置換アリールが、
２位および６位に水素原子またはハロゲン原子、
４位に水素原子、ハロゲン原子、メチル基または
メトキシ基を有し、かつ３位に特定の置換基を有
するフエニルである新規なＮ−アリール−３，
４，５，６−テトラヒドロフタルイミド類が除草
剤として極めて優れた特長を示すことを見出し、
本発明に到達した。
すなわち、本発明の要旨は
一般式
式中、
Ａは水素原子またはメチル基を示す。
Ｘは水素原子、ハロゲン原子、メチル基または
メトキシ基を示し、ＹおよびＺは互いに同一また
は相異なる水素原子またはハロゲン原子を示す。
ＵおよびＶは互いに同一または相異なる水素原
子：
The present invention relates to novel tetrahydrophthalimides and herbicides containing them as active ingredients. Conventionally, N-aryl-3,4,5,6-tetrahydrophthalimides have been known to have excellent herbicidal activity, but slight modifications to their structures (type, number, position of substituents, etc.) In many cases, the presence or absence of herbicidal activity, strength, or selectivity of a new compound differs significantly depending on the compound, and it is difficult to predict the herbicidal activity or selectivity of a new compound based on mere chemical structural similarity. The present inventors conducted intensive research to provide tetrahydrophthalimides with superior herbicidal activity and crop safety, and found that N-substituted aryl
Hydrogen atoms or halogen atoms at the 2nd and 6th positions,
Novel N-aryl-3, which is phenyl having a hydrogen atom, halogen atom, methyl group or methoxy group at the 4-position and a specific substituent at the 3-position.
We discovered that 4,5,6-tetrahydrophthalimides exhibit extremely excellent characteristics as herbicides,
We have arrived at the present invention. That is, the gist of the present invention is the general formula In the formula, A represents a hydrogen atom or a methyl group. X represents a hydrogen atom, a halogen atom, a methyl group or a methoxy group, and Y and Z represent hydrogen atoms or halogen atoms which are the same or different from each other. U and V are hydrogen atoms that are the same or different from each other:
【式】で表わされる基：ハロゲン
原子、アルコキシ基、シアノ基およびハロゲン原
子で置換されていてもよいアリール基から選ばれ
る置換基で置換されていてもよいアルキル基：ア
ルコキシカルボニル基またはシアノ基で置換され
ていてもよいアルケニル基：アルキニル基：
Group represented by [Formula]: Alkyl group optionally substituted with a substituent selected from a halogen atom, an alkoxy group, a cyano group, and an aryl group optionally substituted with a halogen atom: an alkoxycarbonyl group or a cyano group. Optionally substituted alkenyl group: Alkynyl group:
【式】で表わされる基またはアルキルスルホ
ニル基を示す。
上記置換基中、
R1は水素原子、アルキル基またはフエニル基
を示し、R2は水素原子またはメチル基を示し、
ｎは１〜６の整数を示す。
Ｂは−OR3、−SR4、またはIndicates a group represented by the formula or an alkylsulfonyl group. In the above substituents, R 1 represents a hydrogen atom, an alkyl group or a phenyl group, R 2 represents a hydrogen atom or a methyl group,
n represents an integer of 1 to 6. B is −OR 3 , −SR 4 , or
【式】で表わさ れる基を示す。 ＥはR7、OR8、SR9またはIndicates a group represented by [Formula]. E is R 7 , OR 8 , SR 9 or
【式】で表わさ
れる基またはハロゲン原子で置換されていてもよ
いアルキル基：アルケニル基；ハロゲン原子で置
換されていてもよいアリール基または水素原子を
示す。
上記置換基中、
R3は水素原子、アルキル基、アルケニル基、
アルキニル基、シクロアルキル基、アリール基、
アラルキル基またはA group represented by the formula or an alkyl group optionally substituted with a halogen atom: an alkenyl group; an aryl group optionally substituted with a halogen atom or a hydrogen atom. Among the above substituents, R 3 is a hydrogen atom, an alkyl group, an alkenyl group,
Alkynyl group, cycloalkyl group, aryl group,
aralkyl group or
【式】で表わされる
基を示す。
R4はアルキル基を示す。
R5およびR6は互いに同一または相異なる水素
原子、アルキル基、アルコキシ基、アルコキシア
ルキル基、アルケニル基、アルキニル基、アリー
ル基、アラルキル基、シクロアルキル基、アルキ
ルスルホニル基またはIndicates a group represented by [Formula]. R 4 represents an alkyl group. R 5 and R 6 are the same or different hydrogen atoms, alkyl groups, alkoxy groups, alkoxyalkyl groups, alkenyl groups, alkynyl groups, aryl groups, aralkyl groups, cycloalkyl groups, alkylsulfonyl groups, or
【式】で表わされ
る基を示すか、またはR5およびR6は式中の窒素
原子とともに酸素原子を含んでいてもよい複素環
基を示す。
R7はハロゲン原子で置換されていてもよいア
ルキル基：アルケニル基またはハロゲン原子で置
換されていてもよいアリール基を示す。
R8はアルキル基、シクロアルキル基、アラル
キル基またはアリール基を示す。
R9はアルキル基またはアリール基を示す。
R10およびR11は同一または相異なるアルキル
基、アルコキシ基またはハロゲンで置換されてい
てもよいアリール基を示す。
上記置換基中、
R12は水素原子またはアルキル基を示す。
Ｄは水酸基、アルコキシ基または１個または２
個のアルキル基またはアルケニル基で置換されて
いてもよいアミノ基を示す。
但し、Ｘが塩素原子を表わし、かつＹおよびＺ
が同時に水素原子を表わすとき、ＵおよびＶが下
記表に示される組合せを表わすことはない。It represents a group represented by the formula, or R 5 and R 6 represent a heterocyclic group which may contain an oxygen atom together with the nitrogen atom in the formula. R 7 represents an alkyl group optionally substituted with a halogen atom: an alkenyl group or an aryl group optionally substituted with a halogen atom. R 8 represents an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group. R 9 represents an alkyl group or an aryl group. R 10 and R 11 represent the same or different alkyl groups, alkoxy groups, or aryl groups which may be substituted with halogen. In the above substituents, R 12 represents a hydrogen atom or an alkyl group. D is a hydroxyl group, an alkoxy group, or 1 or 2
represents an amino group which may be substituted with an alkyl group or an alkenyl group. However, X represents a chlorine atom, and Y and Z
When simultaneously represent a hydrogen atom, U and V do not represent the combinations shown in the table below.
【表】【table】
【表】
で表わされるテトラヒドロフタルイミド類および
これを有効成分とする除草剤にある。
次に本発明を具体例に説明する。
本発明において除草剤として用いられるテトラ
ヒドロフタルイミド類は、前記一般式（）で表
わされる。好ましくは、前記一般式（）乃至一
般式（）で表わされる。式中、Ａは水素原子、
３−メチル基または４−メチル基を示し、Ｘは水
素原子、弗素原子、塩素原子、臭素原子等のハロ
ゲン原子、メチル基またはメトキシ基を示し、Ｙ
およびＺは水素原子または弗素原子、塩素原子、
臭素原子等のハロゲン原子を示し、ＵおよびＶは
互いに同一または相異なる水素原子；
[Table] Tetrahydrophthalimides and herbicides containing them as active ingredients. Next, the present invention will be explained using a specific example. The tetrahydrophthalimide used as a herbicide in the present invention is represented by the above general formula (). Preferably, it is represented by the above general formula () to general formula (). In the formula, A is a hydrogen atom,
3-methyl group or 4-methyl group, X represents a halogen atom such as a hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl group or methoxy group,
and Z is a hydrogen atom, a fluorine atom, a chlorine atom,
Represents a halogen atom such as a bromine atom, and U and V are hydrogen atoms that are the same or different from each other;
【式】で表わされる基〔式中、R1は水
素原子、C1〜C12のアルキル基好ましくはC1〜C8
のアルキル基更に好ましくはC1〜C6のアルキル
基、またはフエニル基を示し、R2は水素原子ま
たはメチル基を示し、ｎは１〜６の整数好ましく
は１〜４の整数を示し、Ｂは−OR3｛式中、R3は
水素原子、C1〜C30のアルキル基好ましくはC1〜
C20のアルキル基更に好ましくはC1〜C12のアルキ
ル基、C2〜C6のアルケニル基好ましくはC3〜C4
のアルケニル基、C2〜C6のアルキニル基好まし
くはC3〜C4のアルキニル基、C3〜C8のシクロア
ルキル基好ましくはC5〜C7のシクロアルキル基、
フエニル基等のアリール基、ベンジル基等のアラ
ルキル基、またはA group represented by [formula] [wherein R 1 is a hydrogen atom, a C 1 to C 12 alkyl group, preferably a C 1 to C 8
more preferably a C 1 to C 6 alkyl group or a phenyl group, R 2 represents a hydrogen atom or a methyl group, n represents an integer of 1 to 6, preferably an integer of 1 to 4, B is -OR 3 {wherein R 3 is a hydrogen atom, a C 1 to C 30 alkyl group, preferably a C 1 to
C20 alkyl group, more preferably C1 - C12 alkyl group, C2 - C6 alkenyl group, preferably C3 - C4
a C2 - C6 alkynyl group, preferably a C3 - C4 alkynyl group, a C3 - C8 cycloalkyl group, preferably a C5 - C7 cycloalkyl group,
Aryl group such as phenyl group, aralkyl group such as benzyl group, or
【式】で表わされる基
（式中、R12は水素原子またはC1〜C6のアルキル
基好ましくはC1〜C4のアルキル基を示し、Ｄは
水酸基、C1〜C4のアルコキシ基、または１個ま
たは２個のC1〜C8のアルキル基好ましくはC1〜
C5のアルキル基またはC3〜C4のアルケニル基で
置換されていてもよいアミノ基を示す）を示す｝、
−SR4（式中、R4はC1〜C10のアルキル基好ましく
はC2〜C5のアルキル基を示す）、または
A group represented by the formula (wherein R 12 is a hydrogen atom or a C 1 to C 6 alkyl group, preferably a C 1 to C 4 alkyl group, and D is a hydroxyl group or a C 1 to C 4 alkoxy group) , or one or two C1 - C8 alkyl groups, preferably C1- C8
represents an amino group optionally substituted with a C 5 alkyl group or a C 3 to C 4 alkenyl group},
-SR 4 (wherein R 4 represents a C 1 to C 10 alkyl group, preferably a C 2 to C 5 alkyl group), or
【式】｛式中、R5およびR6は同一または相
異なる水素原子、C1〜C30のアルキル基好ましく
はC1〜C20のアルキル基更に好ましくはC1〜C12の
アルキル基、C1〜C12のアルコキシ基好ましくは
C1〜C8のアルコキシ基更に好ましくはC1〜C4の
アルコキシ基、C2〜C8のアルコキシアルキル基
好ましくはC2〜C6のアルコキシアルキル基更に
好ましくはC2〜C4のアルコキシアルキル基、C2
〜C8のアルケニル基好ましくはC3〜C5のアルケ
ニル基、C2〜C8のアルキニル基好ましくはC3〜
C5のアルキル基、フエニル基等のアリール基、
ベンジル基等のアラルキル基、C3〜C8のシクロ
アルキル基好ましくはC3〜C6のシクロアルキル
基、C1〜C8のアルキルスルホニル基好ましくは
C1〜C5のアルキルスルホニル基、または
[Formula] {wherein R 5 and R 6 are the same or different hydrogen atoms, a C 1 to C 30 alkyl group, preferably a C 1 to C 20 alkyl group, more preferably a C 1 to C 12 alkyl group, C1 - C12 alkoxy group preferably
C1 - C8 alkoxy group, more preferably C1 - C4 alkoxy group, C2 - C8 alkoxyalkyl group, preferably C2 - C6 alkoxyalkyl group, more preferably C2 - C4 alkoxy Alkyl group, C2
~ C8 alkenyl group, preferably C3 ~ C5 alkenyl group, C2 ~ C8 alkynyl group, preferably C3 ~
C5 alkyl group, aryl group such as phenyl group,
Aralkyl group such as benzyl group, C3 - C8 cycloalkyl group, preferably C3 - C6 cycloalkyl group, preferably C1 - C8 alkylsulfonyl group
C1 - C5 alkylsulfonyl group, or
【式】で表わされる基（式中、R12およ
びＤは前記と同義を示す）を示すか、またはR5
およびR6は式中の窒素原子とともに酸素原子を
含んでいてもよい５〜７員の複数環基好ましくは
５〜７員の飽和複素環基を示す｝で表わされる基
を示す〕；弗素原子または塩素原子等のハロゲン
原子好ましくは塩素原子、C1〜C4のアルコキシ
基、シアノ基、および塩素原子等のハロゲン原子
で置換されていてもよいアリール基好ましくはフ
エニル基等の置換基で置換されてもよいC1〜C6
のアルキル基好ましくはC1〜C4のアルキル基；
１個または２個のC2〜C5のアルコキシカルボニ
ル基またはシアノ基で置換されていてもよいC2
〜C6のアルケニル基好ましくはC2〜C4のアルケ
ニル基；C2〜C6のアルキニル基好ましくはC3〜
C4のアルキニル基；represents a group represented by [Formula] (in the formula, R 12 and D have the same meanings as above), or R 5
and R 6 represents a 5- to 7-membered multicyclic group, preferably a 5- to 7-membered saturated heterocyclic group, which may contain an oxygen atom together with the nitrogen atom in the formula]; a fluorine atom or a halogen atom such as a chlorine atom, preferably a chlorine atom, a C1 to C4 alkoxy group, a cyano group, and an aryl group optionally substituted with a halogen atom such as a chlorine atom, preferably a substituent such as a phenyl group C 1 to C 6 which may be
an alkyl group, preferably a C 1 -C 4 alkyl group;
C2 optionally substituted with one or two C2 - C5 alkoxycarbonyl groups or cyano groups
~ C6 alkenyl group, preferably C2 ~ C4 alkenyl group; C2 ~ C6 alkynyl group, preferably C3 ~
C4 alkynyl group;
【式】で表わされる基
〔式中、Ｅは−R7（式中、R7は１〜３個のハロゲ
ン原子好ましくは弗素原子または塩素原子で置換
されていてもよいC1〜C5のアルキル基好ましく
はC1〜C3のアルキル基、C2〜C5のアルケニル基
好ましくはC3〜C4のアルケニル基、または塩素
原子等のハロゲン原子で置換されていてもよいア
リール基好ましくはフエニル基を示す）、−OR8
（式中、R8はC1〜C12のアルキル基好ましくはC1
〜C8のアルキル基、C3〜C8のシクロアルキル基
好ましくはC5〜C7のシクロアルキル基、C7〜C9
のアラルキル基好ましくはベンジル基、またはフ
エニル基等のアリール基を示す）、−SR9（式中、
R9はC1〜C6のアルキル基好ましくはC1〜C4のア
ルキル基、またはフエニル基等のアリール基を示
す）、またはA group represented by the formula [wherein E is -R 7 (wherein R 7 is a C 1 to C 5 group which may be substituted with 1 to 3 halogen atoms, preferably a fluorine atom or a chlorine atom)] Alkyl group, preferably a C1 - C3 alkyl group, a C2 - C5 alkenyl group, preferably a C3 - C4 alkenyl group, or an aryl group optionally substituted with a halogen atom such as a chlorine atom, preferably phenyl group), -OR 8
(In the formula, R 8 is a C 1 to C 12 alkyl group, preferably C 1
-C8 alkyl group, C3 - C8 cycloalkyl group, preferably C5 - C7 cycloalkyl group, C7 - C9
an aralkyl group, preferably a benzyl group or an aryl group such as a phenyl group), -SR 9 (in the formula,
R 9 represents a C 1 to C 6 alkyl group, preferably a C 1 to C 4 alkyl group, or an aryl group such as a phenyl group), or
【式】（式中、R10およびR11は
同一または相異なる水素原子、C1〜C4のアルキ
ル基好ましくはC1〜C2のアルキル基、C1〜C4の
アルコキシ基好ましくはC1〜C2のアルコキシ基、
または塩素原子等のハロゲン原子で置換されてい
てもよいアリール基好ましくはフエニル基を示
す）で表わされる基を示す〕またはC1〜C4のア
ルキルスルホニル基好ましくはC1〜C2のアルキ
ルスルホニル基を示す。
但し、Ｘが塩素原子を表わし、かつＹおよびＺ
が同時に水素原子を表わすとき、ＵおよびＶが下
記表に示される組合せを表わすことはない。[Formula] (where R 10 and R 11 are the same or different hydrogen atoms, a C 1 to C 4 alkyl group, preferably a C 1 to C 2 alkyl group, a C 1 to C 4 alkoxy group, preferably a C 1 - C2 alkoxy group,
or an aryl group optionally substituted with a halogen atom such as a chlorine atom, preferably a phenyl group] or a C1 - C4 alkylsulfonyl group, preferably a C1 - C2 alkylsulfonyl Indicates the group. However, X represents a chlorine atom, and Y and Z
When simultaneously represent a hydrogen atom, U and V do not represent the combinations shown in the table below.
【表】【table】
【表】
本発明の式（）で示される化合物は、場合に
より光学異性体またはジアステレオマーなどの異
性体が存在し得る。多くの場合、該異性体は全て
の異性体を含む混合物として得られる。これらの
異性体は既知の様々な方法（例えば、不斉合成、
不斉炭素源を有する出発原料を利用する合成、光
学分割、再結晶、またはカラムクロマトグラフイ
ー、薄層クロマトグラフイー、高速液体クロマト
グラフイーなどの各種クロマトグラフイー）によ
つてそれぞれの異性体を得ることも可能である。
ジアステレオマーの分離例を実施例No.５として示
す。
式（）で示される化合物は各種原料を用いて
下記反応式に従つて製造することができる。
（上記反応式中、Ａ、Ｘ、ＹおよびＺは前記と同
義を示す）
上記還元反応は酢酸、エタノール、酢酸エチ
ル、ベンゼン、トルエン等の溶媒中、パラジウ
ム、ラネーニツケル等の触媒の存在下に、常圧ま
たは加圧下０〜150℃にて行われる。尚、出発原
料となるＮ−（３−ニトロフエニル）−３，４，
５，６−（テトラヒドロフタルイミド類はシクロ
ヘキセン−１，２−ジカルボン酸無水物とニトロ
アニリン類とを無溶媒または酢酸、メタノール、
トルエン、ジオキサン、水等の溶媒中60〜200゜に
て反応することにより容易に得ることができ、か
つ、それを単離することなく本還元反応に付すこ
とも可能である。
（上記反応式中、Ａ、Ｘ、Ｙ、Ｚ、ＵおよびＶは
前記と同義を示す）
上記シクロヘキセン−１，２−ジカルボン酸無
水物とｎ−フエニレンジアミン類との反応は無溶
媒または酢酸、メタノール、トルエン、ジオキサ
ン、水等の溶媒中60〜200℃で行われる。
（上記反応式中、Ａ、Ｘ、Ｙ、Ｚ、ＵおよびＶは
前記と同義を示し、V′およびU′は水素原子：
[Table] The compound represented by the formula () of the present invention may exist in isomers such as optical isomers or diastereomers. In many cases, the isomers are obtained as a mixture containing all isomers. These isomers can be obtained by various known methods (e.g. asymmetric synthesis,
Each isomer is synthesized using a starting material having an asymmetric carbon source, optical resolution, recrystallization, or various chromatography methods such as column chromatography, thin layer chromatography, and high performance liquid chromatography). It is also possible to obtain
An example of separation of diastereomers is shown as Example No. 5. The compound represented by the formula () can be produced using various raw materials according to the reaction formula below. (In the above reaction formula, A, X, Y and Z have the same meanings as above) The above reduction reaction is carried out in a solvent such as acetic acid, ethanol, ethyl acetate, benzene, toluene, etc. in the presence of a catalyst such as palladium or Raney nickel, It is carried out at 0 to 150°C under normal pressure or increased pressure. In addition, the starting material N-(3-nitrophenyl)-3,4,
5,6-(Tetrahydrophthalimides are prepared by combining cyclohexene-1,2-dicarboxylic anhydride and nitroanilines without solvent or with acetic acid, methanol,
It can be easily obtained by reaction at 60 to 200° in a solvent such as toluene, dioxane, water, etc., and can also be subjected to the main reduction reaction without isolation. (In the reaction formula, A, , carried out at 60-200 °C in a solvent such as methanol, toluene, dioxane, water, etc. (In the above reaction formula, A, X, Y, Z, U and V have the same meanings as above, and V' and U' are hydrogen atoms:
【式】で表わされる基：ハロゲン原
子、アルコキシ基、シアノ基およびハロゲン原子
で置換されていてもよいアリール基から選ばれる
置換基で置換されていてもよいアルキル基：アル
ケニル基：アルキニル基またはアルキルスルホニ
ル基を示し、但し、Ｘが塩素原子を表わし、かつ
ＹおよびＺが同時に水素原子を表わすとき、Ｕお
よびＶが下記表に示される組合せを表わすことは
ない。Group represented by [Formula]: Alkyl group optionally substituted with a substituent selected from a halogen atom, an alkoxy group, a cyano group, and an aryl group optionally substituted with a halogen atom: Alkenyl group: Alkynyl group or alkyl group represents a sulfonyl group, provided that when X represents a chlorine atom and Y and Z simultaneously represent a hydrogen atom, U and V do not represent the combinations shown in the table below.
【表】【table】
【表】
Ｑはハロゲン原子または場合によりメシラー
ト、トシラート、メトキシ基またはエトキシ基な
どのアルコキシ基を示すか、ＱはＵとともに酸無
水物または混合酸無水物を示す）
本反応は無溶媒またはテトラヒドロフラン、ジ
オキサン、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，
Ｎ−ジメチルアセトアミド、ジメチルスルホキシ
ド、スルホラン、ベンゼン、トルエン、キシレ
ン、クメン、クロルベンゼン、ジクロルベンゼ
ン、塩化メチレン、クロロホルム、四塩化炭素、
トリクレン、酢酸エチル、アセトン、エチルメチ
ルケトン、エーテル、ジイソプロピルエーテル等
の溶媒中、酢酸ナトリウム、炭酸水素カリウム、
炭酸ナトリウム、炭酸カリウム、水酸化ナトリウ
ム、水酸化カリウム、水酸化バリウム、水酸化カ
ルシウム、金属リチウム、金属ナトリウム、金属
カリウム、水素化ナトリウム、水素化カリウム、
ナトリウムアミド、塩化リチウム、塩化ナトリウ
ム、塩化カリウム、塩化マグネシウム、塩化亜
鉛、塩化鉄（）、塩化鉄（）、塩化銅（）、
塩化銅（）、沃化リチウム、沃化ナトリウム、
沃化カリウム、弗化カリウム、弗化セシウム、酸
化亜銅、酸化カルシウム、酸化バリウム、酸化鉄
（）、酸化鉄（）、炭酸鉛、ピリジン、４−ジ
メチルアミノピリジン、トリエチルアミン、Ｎ，
Ｎ−ジエチルアニリン、ベンジルトリメチルアン
モニウムクロリド（ブロミド）、ベンジルトリエ
チルアンモニウムクロリド（ブロミド）、テトラ
ｎ−ブチルアンモニウムブロミド（ヨージド）、
クラウンエーテル類；ポリオキシエチレン類等の
存在下または不存在下−20〜250℃好ましくは０
〜200℃にて行われる。
（上記反応式中、Ａ、ＵおよびＶは前記と同義を
示し、Ｘ、ＹおよびＺの少くとも１つはハロゲン
原子を、他は前記と同義を示し、X′、Y′および
Z′の少くとも１つは水素原子を、他は対応する
Ｘ、ＹおよびＺと同義を示す）
本反応は酢酸、クロロホルム、四塩化炭素、ベ
ンゼン、クロルベンゼン等の溶媒中、塩素、臭
素、塩化スルフリル、Ｎ−クロルスクシンイミ
ド、Ｎ−ブロムスクシンイミド等のハロゲン化剤
を、−70〜150℃好ましくは−20〜120℃にて作用
せしめて行われる。
（上記反応式中、Ａ、Ｘ、Ｙ、Ｚ、R1、R2およ
びｎは前記と同義を示し、ＵおよびＶは水素原
子、アルキル基、アルケニル基またはアルキニル
基を示し、Ｂは−OR3、−SR4または[Table] Q represents a halogen atom or an alkoxy group such as mesylate, tosylate, methoxy group or ethoxy group, or Q represents an acid anhydride or mixed acid anhydride together with U) This reaction can be carried out without a solvent or with tetrahydrofuran, Dioxane, N,N-dimethylformamide, N,
N-dimethylacetamide, dimethylsulfoxide, sulfolane, benzene, toluene, xylene, cumene, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride,
Sodium acetate, potassium hydrogen carbonate, in a solvent such as tricrene, ethyl acetate, acetone, ethyl methyl ketone, ether, diisopropyl ether, etc.
Sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide, metallic lithium, metallic sodium, metallic potassium, sodium hydride, potassium hydride,
Sodium amide, lithium chloride, sodium chloride, potassium chloride, magnesium chloride, zinc chloride, iron chloride (), iron chloride (), copper chloride (),
Copper chloride (), lithium iodide, sodium iodide,
Potassium iodide, potassium fluoride, cesium fluoride, cuprous oxide, calcium oxide, barium oxide, iron oxide (), iron oxide (), lead carbonate, pyridine, 4-dimethylaminopyridine, triethylamine, N,
N-diethylaniline, benzyltrimethylammonium chloride (bromide), benzyltriethylammonium chloride (bromide), tetra n-butylammonium bromide (iodide),
Crown ethers; -20 to 250°C, preferably 0 in the presence or absence of polyoxyethylenes, etc.
Performed at ~200°C. (In the above reaction formula, A, U and V have the same meanings as above, at least one of X, Y and Z represents a halogen atom, the others have the same meanings as above, X', Y' and
(At least one of Z' represents a hydrogen atom, and the others have the same meaning as the corresponding X, Y, and Z.) This reaction is performed in a solvent such as acetic acid, chloroform, carbon tetrachloride, benzene, chlorobenzene, etc., using chlorine, bromine, The reaction is carried out using a halogenating agent such as sulfuryl chloride, N-chlorosuccinimide, N-bromsuccinimide, etc. at -70 to 150°C, preferably -20 to 120°C. (In the above reaction formula , A, 3 , −SR 4 or
【式】を
示し、R3、R4、R5およびR6は前記と同義を示
す）
上記加水分解反応は、(i)水、水−メタノール、
水−エタノール、水−ジオキサン等の溶媒中、塩
酸、硫酸等の酸の存在下０〜120℃、または蟻酸、
酢酸等の溶媒中、メタンスルホン酸、ｐ−トルエ
ンスルホン酸等の存在下80〜180℃で行われる：
(ii)Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチル−
２−ピロリドン、２，４，６−コリジン、２，６
−ルチジン、ピリジン等の溶媒中、水酸化リチウ
ム、臭化リチウム、沃化リチウム、沃化ナトリウ
ム等の存在下100〜200℃で行われる：(iii)水、水−
メタノール、水−エタノール、水−ジオキサン、
水−アセトンなどの溶媒中、水酸化ナトリウム、
水酸化カリウム、水酸化バリウム等の存在下−20
〜150℃にて反応後溶媒を留去し、残留物を酢酸、
希塩酸、希塩酸−ジオキサンなどの溶媒中50〜
200℃にて反応することにより行われる。
（上記反応式中、Ａ、Ｘ、Ｙ、Ｚ、R1、R2およ
びｎは前記と同義を示し、ＵおよびＶは水素原
子、アルキル基、アルケニル基またはアルキニル
基を示し、Ｂは−OR3、−SR4または[Formula] and R 3 , R 4 , R 5 and R 6 have the same meanings as above) The above hydrolysis reaction consists of (i) water, water-methanol,
In a solvent such as water-ethanol or water-dioxane, in the presence of an acid such as hydrochloric acid or sulfuric acid, at 0 to 120°C, or formic acid,
Performed at 80-180°C in a solvent such as acetic acid in the presence of methanesulfonic acid, p-toluenesulfonic acid, etc.:
(ii) N,N-dimethylformamide, N-methyl-
2-pyrrolidone, 2,4,6-collidine, 2,6
-Carried out at 100-200°C in a solvent such as lutidine or pyridine in the presence of lithium hydroxide, lithium bromide, lithium iodide, sodium iodide, etc.: (iii) Water, water-
methanol, water-ethanol, water-dioxane,
In a solvent such as water-acetone, sodium hydroxide,
In the presence of potassium hydroxide, barium hydroxide, etc. -20
After the reaction at ~150°C, the solvent was distilled off and the residue was diluted with acetic acid,
50~ in solvents such as dilute hydrochloric acid, dilute hydrochloric acid-dioxane, etc.
This is done by reacting at 200°C. (In the above reaction formula , A, 3 , −SR 4 or
【式】を
示し、R3、R4、R5およびR6は前記と同義を示
す）
上記反応は、無溶媒またはベンゼン、トルエ
ン、塩化メチレン、クロロホルム、四塩化炭素、
テトラヒドロフラン、ジオキサン、エーテル、ア
セトニトリル、ピリジン、Ｎ，Ｎ−ジメチルホル
ムアミド等の溶媒中、塩酸、硫酸、燐酸、メタン
スルホン酸、ｐ−トルエンスルホン酸、塩化チオ
ニル、オキシ塩化燐、クロル炭酸メチル、クロル
炭酸エチル、Ｎ，N′−ジシクロヘキシルカルボ
ジイミド等の存在下、炭酸水素ナトリウム、炭酸
水素カリウム、炭酸ナトリウム、炭酸カリウム、
水酸化ナトリウム、水酸化カリウム、ピリジン、
トリエチルアミン、Ｎ，Ｎ−ジエチルアニリン等
の塩基の存在下または不存在下−20〜150゜にて行
われる。
本縮合反応においては、出発物質であるカルボ
ン酸類は、場合により酸塩化物、酸無水物、混合
酸無水物等の各種中間体を形成し、各種アルコー
ル類、メルカプタン類、アミン類等と反応するこ
とより目的化合物を生成する。これらの中間体を
単離して用いることも場合により可能である。
（上記反応式中、Ａ、Ｘ、Ｙ、Ｚ、R1、R2、ｎ
およびR3は前記と同義を示し、ＵおよびＶは水
素原子またはアルキル基を示し、Ｑは塩素、臭
素、沃素等のハロゲン原子またはメシラート、ト
シラート等を示す）
上記反応は、アセトン、エチルメチルケトン、
アセトニトリル、ベンゼン、トルエン、Ｎ，Ｎ−
ジメチルホルムアミド、テトラヒドロフラン、ジ
オキサン等の溶媒中、炭酸ナトリウム、炭酸カリ
ウム、水酸化ナトリウム、水酸化カリウム、金属
ナトリウム、金属カリウム、水素化ナトリウム、
弗化カリウム、弗化セシウム等の存在下、０〜
180℃にて行われる。
かくして得られる本発明の化合物はそのままで
も除草剤として使用できるが、通常、不活性な液
体担体または固体と混合し、これに適当な界面活
性剤などを加え、乳剤、粉剤、粒剤、錠剤、水和
剤等の形態として使用する。
液体担体としては、トルエン、キシレン、メチ
ルナフタレン、シクロヘキサン、ブタノール、グ
リコール、ジメチルスルホキシド、ジメチルホル
ムアミド、アセトン、メチルイソブチルケトン、
動植物性油、脂肪酸、脂肪酸エステル、水など
が、また固体担体としては、粘土、カオリンクレ
ー、タルク、ベントナイト、硅藻土、シリカ、炭
酸カルシウムおよびダイズ粉、コムギ粉等の植物
性粉末などがあげられる。さらに必要があれば、
他の活性成分、例えば農業用殺菌剤、殺虫剤、殺
線虫剤または他の除草剤、植物生長調節剤、土壌
改良剤および肥料などと混ぜて使用することもで
きる。また、確実な除草効果を得るため、展着
剤、乳化剤、湿展剤、固着剤などの補助剤を適当
に混合してもよい。
本発明の除草剤の施用量は、当然選ばれる化合
物の種類、対象雑草、処理時期、処理方法または
土壌の性質などの状況によつて異なるが、通常有
効成分として１アール当り0.1〜80gr、好ましく
は0.5〜20grの範囲が適当である。
本発明の除草剤は移植水田での雑草発芽前湛水
土壌処理または生育期処理のいずれにも使用可能
であり、１年生雑草および多年生雑草に対し高い
殺草活性を示し、加えて移植水稲に対する影響が
極めて少ないという水田用除草剤として極めて好
ましい性質を有する特徴がある。
また畑作での雑草発芽前土壌処理および茎葉兼
土壌処理においても、１年生雑草および多年生雑
草に対し優れた殺草活性と十分な残効性とを示
し、高濃度で処理した場合においても作物に対す
る影響が極めて軽微であるという優れた特徴を有
している。特に、今まで既存の除草剤では防除困
難とされてきた、野性アサガオ、チヨウセンアサ
ガオ、イチビ等にも他の雑草と同様に卓効を示す
ことが特徴である。
本発明化合物は、例えば次の雑草を防除するの
に用いられる。
双子葉植物である雑草、例えば野性アサガオ、
シロザ、イヌタデ、チヨウセンアサガオ、イチ
ビ、ヤエムグラ、シロカラシナ、野性カラシナ、
ハコベ、ハキダメギク、ギシギシ、イヌビユ、ブ
タクサ、オナモミ、カミルレ、キカシグサ、アゼ
ナ、タカサブロウ、タウコギ、アブノメ、ミゾハ
コベ、ミゾソバ。
単子葉植物である雑草、例えばタイヌビエ、メ
ヒシバ、オヒシバ、エノコログサ、スズメノカタ
ビラ、スズメノテツポウ、ギヨウギシバ、シバム
ギ、カヤツリグサ、タマガヤツリ、クログワイ、
マツバイ、ホタルイ、ミズガヤツリ、コウキヤガ
ラ、コナギ、ウリカワ、ヘラオモダカ、オモダ
カ。
本発明化合物は、例えば次の作物の栽培におい
て選択的除草剤として使用できる。
双子葉植物である栽培作物：ダイズ、ワタ、テ
ンサイ、ヒマワリ、エンドウ、ジヤガイモ、キユ
ウリ。
単子葉植物である栽培作物：イネ、コムギ、オ
オムギ、カラスムギ、ライムギ、トウモロコシ、
サトウキビ。
本発明化合物の適用範囲は以上の種類の植物の
みに限定されるものではなく、他の植物に対して
も同様な施用方法により使用することができる。
次に本発明を実施例をあげて、さらに具体的に
説明するが、本発明はその要旨を超えない限り、
以下の実施例に限定するものではない。
実施例 １
Ｎ−（５−アミノ−４−クロル−２−フルオル
フエニル）−３，４，５，６−テトラヒドロフ
タルイミドの製造
シクロヘキサン−１，２−ジカルボン酸無水物
と４−クロル−２−フルオル−５−ニトロアニリ
ンとを酢酸中加熱することにより得たＮ−（４−
クロル−２−フルオル−５−ニトロフエニル）−
３，４，５，６−テトラヒドロフタルイミド
（mp.136〜138℃）60.0gおよびベンゼン250mlの
混合物を５％パラジウム／炭素の存在下に55℃に
て接触還元を行つた。還元後触媒を別し、溶媒
を留去すると結晶が得られた。これをベンゼン−
ｎ−ヘキサンより再結晶し表１記載の化合物（No.
277）50.8gを得た。
実施例 ２
Ｎ−（３−アミノ−４−クロルフエニル）−３，
４，５，６−テトラヒドロフタルイミドの製造
シクロヘキセン−１，２−ジカルボン酸無水物
16.0g、４−クロル−ｍ−フエニレンジアミン
14.3gおよび水200mlの混合物を撹拌しつつ100℃
にて９時間反応した。冷後、析出せる結晶を取
し表１記載の化合物（No.270）26.8gを得た。
実施例 ３
Ｎ−〔２−フルオル−５−〔１−（１−メチルプ
ロピルカルバモイル）エチル〕アミノフエニ
ル〕−３，４，５，６−テトラヒドロフタルイ
ミド類の調製
２−（４−フルオル−３−ニトロフエニルアミ
ノ）−Ｎ−（１−メチルプロピル）プロピオンアミ
ド7.86gを酢酸35ml中５％パラジウム／炭素の存
在下に接触還元した後触媒を別した。生成した
２−（３−アミノ−４−フルオルフエニル）アミ
ノ−Ｎ−（１−メチルプロピル）プロピオンアミ
ドを単離することなく、液にシクロヘキセン−
１，２−ジカルボン酸無水物4.21gを加え、２時
間撹拌しつつ加熱還流後、溶媒を留去した。酢酸
エチル50mlを加え、水洗、芒硝乾燥後溶媒を留去
し、残留物をシリカゲルカラム（展開溶媒系酢酸
エチル−ｎ−ヘキサン３：２）で精製し、表１記
載の化合物（No.51）8.30gを得た。
尚、原料として用いた２−（４−フルオル−３
−ニトロフエニル）アミノ−Ｎ−（１−メチルプ
ロピル）プロピオンアミドは以下の如く調製し
た。即ち、４−フルオル−３−ニトロアニリン
5.20g、Ｎ−（１−メチルプロピル）−２−ブロム
プロピオンアミドおよび炭酸水素ナトリウム
3.05gの混合物を160℃にて１時間加熱後、シリカ
ゲルカラム（展開溶媒系酢酸エチル−ｎ−ヘキサ
ン１：１）にて精製し、上記プロピオンアミド誘
導体9.19g（mp.101〜102℃）を得た。
実施例 ４
Ｎ−〔４−クロル−３−〔１−（１−メチルプロ
ピル）カルバモイルプロピル〕アミノフエニ
ル〕−３，４，５，６−テトラヒドロフタルイ
ミドの製造
Ｎ−（３−アミノ−４−クロルフエニル）−３，
４，５，６−テトラヒドロフタルイミド2.77g、
２−ブロム−Ｎ−（１−メチルプロピル）酪酸ア
ミド4.44gおよび酸化亜鉛0.41gの混合物を160℃
にて５時間撹拌後室温迄冷却し酢酸エチル30mlを
加えて不溶部を別した。液を減圧濃縮後残留
物をシリカゲルカラム（展開溶媒系酢酸エチル−
ｎ−ヘキサン１：２）にて精製し表１記載の化合
物（No.151）2.72gを得た。
実施例 ５
Ｎ−〔４−クロル−３−〔１−（メチルヘキシル）
カルバモイルエチル〕アミノフエニル〕−３，
４，５，６−テトラヒドロフタルイミドの製造
および生成したジアステレオマー異性体の分離
Ｎ−（３−アミノ−４−クロルフエニル）−３，
４，５，６−テトラヒドロフタルイミド2.77g、
２−ブロム−Ｎ−（１−メチルヘキシル）プロピ
オンアミド6.00gおよび炭酸水素ナトリウムの混
合物を160℃にて2.5時間撹拌後室温迄冷却し酢酸
エチル30mlを加え、水洗、芒硝乾燥した。このも
ののシリカゲル薄層クロマトグラフイー（展開溶
媒系酢酸エチル−ｎ−ヘキサン１：２）はRf0.33
および0.28に２種の生成物を示した。溶媒を留去
後、残留物をシリカゲルカラム（展開溶媒：クロ
ロホルム）にて分離し、表１記載の化合物（No.
77、高Rf値を有する）0.92g、（No.78、低Rf値を有
する）0.93gおよびそれらの混合物0.90gを得た。
実施例 ６
Ｎ−〔５−〔１−（アリルカルバモイル）プロピ
ル〕アミノ−４−クロル−２−フルオルフエニ
ル〕−３，４，５，６−テトラヒドロフタルイ
ミドの製造
Ｎ−（５−アミノ−４−クロル−２−フルオル
フエニル）−３，４，５，６−テトラヒドロフタ
ルイミド2.77g、Ｎ−アリル−２−ブロム酪酸ア
ミド4.12gおよび炭酸水素ナトリウム1.01gの混合
物を150℃にて２時間撹拌後室温迄冷却し、酢酸
エチル０mlを加え水洗、芒硝乾燥後溶媒を留去し
た。残留物をシリカゲルカラム（展開溶媒系、酢
酸エチル−ｎ−ヘキサン１：２）にて精製し表１
記載の化合物（No.175）2.30gを得た。
実施例 ７
Ｎ−〔４−クロル−３−〔１−（２−メチルブチ
ルカルバモイル）プロピル〕アミノフエニル〕
−３，４，５，６−テトラヒドロフタルイミド
の製造
Ｎ−（３−アミノ−４−クロルフエニル）−３，
４，５，６−テトラヒドロフタルイミド2.77g、
Ｎ−（２−メチルブチル）−２−ブロム酪酸アミド
4.60g、炭酸水素ナトリウム1.01g、沃化カリウム
0.38gおよびスルホラン５mlの混合物を160℃にて
３時間撹拌後室温迄冷却し酢酸エチル30mlを加え
水洗、芒硝乾燥後溶媒を留去した。残留物をシリ
カゲルカラム（展開溶媒系酢酸エチル−ｎ−ヘキ
サン１：３）にて精製し表１記載の化合物（No.
166）1.90gを得た。
実施例 ８
Ｎ−〔２，４−ジブロム−５−フルオル３−〔１
−（１−メチルプロピル）カルバモイルエチル〕
アミノフエニル〕−３，４，５，６−テトラヒ
ドロフタルイミドの製造
Ｎ−〔２−フルオル−５−〔１−（１−メチルプ
ロピル）カルバモイルエチル〕アミノフエニル〕
−３，４，５，６−テトラヒドロフタルイミド
1.93gおよび酢酸５mlの溶液に撹拌しつつ室温に
て臭素1.60gを滴加した。0.5時間後酢酸エチル20
mlを加え、水洗、芒硝乾繰後溶媒を留去した。残
留物をシリカゲルカラム（展開溶媒系酢酸エチル
−ｎ−ヘキサン１：１）にて精製し表１記載の化
合物（No.55）3.10gを得た。
実施例 ９
Ｎ−〔２−クロル−３−（１−エトキシカルボニ
ルプロピル）アミノ−６−フルオルフエニル〕
−３，４，５，６−テトラヒドロフタルイミド
の製造
Ｎ−〔５−（１−エトキシカルボニルプロピル）
アミノ−２−フルオルフエニル〕−３，４，５，
６−テトラヒドロフタルイミド1.87gおよびベン
ゼン20mlの溶液に撹拌しつつ10℃にて塩化スルフ
リル0.70gを滴加した。１時間後、溶媒を留去し
残留物をシリカゲルカラム（展開溶媒系酢酸エチ
ル−ｎ−ヘキサン１：２）にて精製し表１記載の
化合物（No.135）0.95gを得た。
実施例 10
Ｎ−〔３−（１−カルボキシエチル）アミノ−４
−メチルフエニル〕−３，４，５，６−テトラ
ヒドロフタルイミドの調製
Ｎ−〔３−（１−エトキシカルボニルエチル）ア
ミノ−４−メチルフエニル〕−３，４，５，６−
テトラヒドロフタルイミド24.0g、水酸化ナトリ
ウム8.9g、水15mlおよびメタノール80mlの混合物
を80℃にて１時間撹拌後溶媒を留去した。残留物
にシクロヘキセン−１，２−ジカルボン酸無水物
2.1gおよび酢酸80mlを加え撹拌しつつ３時間加熱
還流後再び溶媒を留去し、これに酢酸エチル120
mlを加え、水洗、芒硝乾繰後溶媒を留去した。残
留物を酢酸エチル−ｎ−ヘキサンより再結晶して
表１記載の化合物（No.９）15.7gを得た。
実施例 11
Ｎ−〔４−クロル−３−〔１−（Ｎ−メトキシ−
Ｎ−メチルカルバモイル）ブチル〕アミノフエ
ニル〕−３，４，５，６−テトラヒドロフタル
イミドの製造
Ｎ−〔４−クロル−３−（１−カルボキシブチ
ル）アミノフエニル〕−３，４，５，６−テトラ
ヒドロフタルイミド1.88g、ピリジン0.99gおよび
ジクロルメタン15mlの混合物中に、撹拌下７℃に
て塩化チオニル0.65gをジクロルメタン１mlに溶
解せしめたものを滴加し、20分間撹拌した。これ
に、Ｎ，Ｏ−ジメチルヒドロキシルアミン0.39g、
トリエチルアミン0.56gおよびジクロルメタン３
mlの混合物を滴加し、更に1.5時間室温にて撹拌
後、反応液を2N塩酸および水で順次洗浄した。
有機層を芒硝乾繰後溶媒を留去し、残留物をシリ
カゲルカラム（展開溶媒系酢酸エチル−ｎ−ヘキ
サン４：７）にて精製し表１記載の化合物（No.
208）1.85gを得た。
実施例 12
Ｎ−〔４−クロル−３−〔１−（１−エトキシカ
ルボニルブチルオキシカルボニル）エチル〕ア
ミノフエニル〕−３，４，５，６−テトラヒド
ロフタルイミドの調製
Ｎ−〔４−クロル−３−（１−カルボキシエチ
ル）アミノフエニル〕−３，４，５，６−テトラ
ヒドロフタルイミド1.74g、２−ブロム吉草酸エ
チルエステル1.15g、弗化カリウム0.64gおよびア
セトニトリル10mlの混合物を撹拌しつつ30時間加
熱還流後、溶媒を留去した。これに酢酸エチル20
mlを加え水洗、芒硝乾繰後溶媒を留去し残留物を
シリカゲルカラム（展開溶媒系酢酸エチル−ｎ−
ヘキサン４：７）で精製し表１記載の化合物（No.
25）1.85gを得た。
実施例 13
Ｎ−〔４−クロル−３−（Ｎ−エトキシカルボニ
ル−Ｎ−プロピル）アミノフエニル〕−３，４，
５，６−テトラヒドロフタルイミドの製造
Ｎ−（４−クロル−３−プロピルアミノフエニ
ル）−３，４，５，６−テトラヒドロフタルイミ
ド1.50g、クロル炭酸エチル0.56g、ピリジン0.45g
および無水テトラヒドロフラン20mlの混合物を撹
拌しつつ２時間加熱還流後溶媒を留去した。残留
物を酢酸エチルで抽出し、水洗、芒硝乾繰後溶媒
を留去し、残留物をシリカゲルカラム（展開溶媒
系酢酸エチル−ｎ−ヘキサン１：３）にて精製
し、表１記載の化合物（No.243）1.25gを得た。
実施例 16
Ｎ−〔４−クロル−３−（Ｎ−メトキシ−Ｎ−メ
チルカルバモイル）アミノフエニル〕−３，４，
５，６−テトラヒドロフタルイミドの製造
Ｎ−（３−アミノ−４−クロルフエニル）−３，
４，５，６−テトラヒドロフタルイミド2.77g、
Ｎ−メトキシ−Ｎ−メチルカルバモイルクロリド
1.19gおよびピリジン10mlの混合物を室温にて12
時間放置後水30mlを加えた。析出せる結晶を取
し、水洗、乾燥後酢酸エチル−ｎ−ヘキサンより
再結晶して表１記載の化合物（No.265）1.99gを得
た。
前示一般式に含まれるその他の化合物も以上で
説明した方法のいずれかによつて製造した。製造
法については後記表１の実施例No.の欄に示した。
尚、表１記載の化合物はすべてIRスペクトル
および／または 1H−NMRスペクトルによつて
確認した。[Formula] and R 3 , R 4 , R 5 and R 6 have the same meanings as above) The above reaction can be carried out without solvent or using benzene, toluene, methylene chloride, chloroform, carbon tetrachloride,
Hydrochloric acid, sulfuric acid, phosphoric acid, methanesulfonic acid, p-toluenesulfonic acid, thionyl chloride, phosphorus oxychloride, methyl chlorocarbonate, chlorocarbonate in a solvent such as tetrahydrofuran, dioxane, ether, acetonitrile, pyridine, N,N-dimethylformamide, etc. In the presence of ethyl, N,N'-dicyclohexylcarbodiimide, etc., sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate,
Sodium hydroxide, potassium hydroxide, pyridine,
The reaction is carried out at -20 to 150° in the presence or absence of a base such as triethylamine or N,N-diethylaniline. In this condensation reaction, carboxylic acids, which are the starting materials, form various intermediates such as acid chlorides, acid anhydrides, and mixed acid anhydrides, depending on the case, and react with various alcohols, mercaptans, amines, etc. In particular, the target compound is produced. It is also possible to isolate and use these intermediates in some cases. (In the above reaction formula, A, X, Y, Z, R 1 , R 2 , n
and R 3 have the same meanings as above, U and V represent a hydrogen atom or an alkyl group, and Q represents a halogen atom such as chlorine, bromine, iodine, mesylate, tosylate, etc.) ,
Acetonitrile, benzene, toluene, N,N-
Sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, metallic sodium, metallic potassium, sodium hydride, in a solvent such as dimethylformamide, tetrahydrofuran, dioxane, etc.
In the presence of potassium fluoride, cesium fluoride, etc., 0-
It is carried out at 180℃. The compound of the present invention thus obtained can be used as a herbicide as it is, but it is usually mixed with an inert liquid carrier or solid, and a suitable surfactant is added thereto to form an emulsion, powder, granule, tablet, etc. Used in the form of hydrating powders, etc. Liquid carriers include toluene, xylene, methylnaphthalene, cyclohexane, butanol, glycol, dimethyl sulfoxide, dimethyl formamide, acetone, methyl isobutyl ketone,
Animal and vegetable oils, fatty acids, fatty acid esters, water, etc., and solid carriers include clay, kaolin clay, talc, bentonite, diatomaceous earth, silica, calcium carbonate, and vegetable powders such as soy flour and wheat flour. It will be done. If you need more,
It may also be used in admixture with other active ingredients such as agricultural fungicides, insecticides, nematicides or other herbicides, plant growth regulators, soil amendments and fertilizers. Further, in order to obtain a reliable herbicidal effect, auxiliary agents such as a spreading agent, an emulsifier, a wetting agent, and a fixing agent may be appropriately mixed. The application amount of the herbicide of the present invention naturally varies depending on the type of compound selected, the target weed, the treatment time, the treatment method, the nature of the soil, etc., but it is usually 0.1 to 80g per are as the active ingredient, preferably A range of 0.5 to 20gr is appropriate. The herbicide of the present invention can be used in either pre-emergence flooded soil treatment or growing season treatment in transplanted rice fields, and exhibits high herbicidal activity against annual and perennial weeds. It has the characteristic that it has extremely favorable properties as a herbicide for paddy fields, with extremely little impact. In addition, pre-emergence soil treatment and foliage and soil treatment in field crops show excellent herbicidal activity and sufficient residual efficacy against annual and perennial weeds, and even when treated at high concentrations, they are effective against crops. It has the excellent feature of having extremely minimal impact. In particular, it is unique in that it is as effective as other weeds, such as wild morning glory, Japanese morning glory, and common weed, which have been considered difficult to control with existing herbicides. The compounds of the present invention can be used, for example, to control the following weeds. Weeds that are dicots, such as wild morning glory,
Shiroza, Japanese knotweed, Japanese morning glory, Ichibi, Yaemugura, white mustard, wild mustard,
Chickweed, leafminer, squeak, dogweed, ragweed, stagweed, chamomile, kikashigusa, azaena, hawkweed, trumpetweed, abnome, chickweed, swamp buckwheat. Weeds that are monocotyledonous plants, such as black-and-white grass, black-and-white grass, black-and-white grass, black-and-white grass, black-and-white grass, grasshopper, silver grass, grasshopper, Japanese cyperus, Japanese cyperus, black grass,
Pinus vulgaris, firefly, water cypera, kouki tita, kosanagi, urikawa, yellow-tailed butterfly, and white-tailed butterfly. The compounds of the invention can be used as selective herbicides, for example in the cultivation of the following crops: Cultivated crops that are dicotyledons: soybeans, cotton, sugar beets, sunflowers, peas, potatoes, and cucumbers. Cultivated crops that are monocots: rice, wheat, barley, oats, rye, corn,
sugar cane. The scope of application of the compound of the present invention is not limited to the above-mentioned types of plants, and can be used for other plants by the same application method. Next, the present invention will be described in more detail with reference to examples, but the present invention will not exceed the gist thereof.
The present invention is not limited to the following examples. Example 1 Production of N-(5-amino-4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide Cyclohexane-1,2-dicarboxylic anhydride and 4-chloro-2- N-(4-
Chlor-2-fluoro-5-nitrophenyl)-
A mixture of 60.0 g of 3,4,5,6-tetrahydrophthalimide (mp. 136-138°C) and 250 ml of benzene was subjected to catalytic reduction at 55°C in the presence of 5% palladium/carbon. After reduction, the catalyst was separated and the solvent was distilled off to obtain crystals. This is benzene
Recrystallized from n-hexane, the compound listed in Table 1 (No.
277) Obtained 50.8g. Example 2 N-(3-amino-4-chlorophenyl)-3,
Production of 4,5,6-tetrahydrophthalimide Cyclohexene-1,2-dicarboxylic anhydride
16.0g, 4-chloro-m-phenylenediamine
A mixture of 14.3 g and 200 ml of water was heated to 100°C with stirring.
The reaction was carried out for 9 hours. After cooling, the precipitated crystals were collected to obtain 26.8 g of the compound (No. 270) listed in Table 1. Example 3 Preparation of N-[2-fluoro-5-[1-(1-methylpropylcarbamoyl)ethyl]aminophenyl]-3,4,5,6-tetrahydrophthalimides 2-(4-fluoro-3-nitro After catalytic reduction of 7.86 g of (phenylamino)-N-(1-methylpropyl)propionamide in the presence of 5% palladium on carbon in 35 ml of acetic acid, the catalyst was separated off. Cyclohexene-
4.21 g of 1,2-dicarboxylic anhydride was added, and the mixture was heated under reflux with stirring for 2 hours, and then the solvent was distilled off. After adding 50 ml of ethyl acetate, washing with water and drying with Glauber's salt, the solvent was distilled off, and the residue was purified with a silica gel column (developing solvent: ethyl acetate-n-hexane 3:2) to form the compound listed in Table 1 (No. 51). Obtained 8.30g. In addition, 2-(4-fluoro-3 used as a raw material)
-Nitrophenyl)amino-N-(1-methylpropyl)propionamide was prepared as follows. That is, 4-fluoro-3-nitroaniline
5.20g, N-(1-methylpropyl)-2-bromopropionamide and sodium bicarbonate
After heating 3.05 g of the mixture at 160°C for 1 hour, it was purified using a silica gel column (developing solvent: ethyl acetate-n-hexane 1:1) to obtain 9.19g (mp. 101-102°C) of the above propionamide derivative. Obtained. Example 4 Production of N-[4-chloro-3-[1-(1-methylpropyl)carbamoylpropyl]aminophenyl]-3,4,5,6-tetrahydrophthalimide N-(3-amino-4-chlorophenyl) -3,
2.77g of 4,5,6-tetrahydrophthalimide,
A mixture of 4.44 g of 2-bromo-N-(1-methylpropyl)butyric acid amide and 0.41 g of zinc oxide was heated at 160°C.
After stirring for 5 hours at room temperature, the mixture was cooled to room temperature, 30 ml of ethyl acetate was added, and the insoluble portion was separated. After concentrating the liquid under reduced pressure, the residue was transferred to a silica gel column (developing solvent: ethyl acetate).
The product was purified with n-hexane (1:2) to obtain 2.72 g of the compound (No. 151) listed in Table 1. Example 5 N-[4-chloro-3-[1-(methylhexyl)
Carbamoylethyl]aminophenyl]-3,
Production of 4,5,6-tetrahydrophthalimide and separation of generated diastereoisomers N-(3-amino-4-chlorophenyl)-3,
2.77g of 4,5,6-tetrahydrophthalimide,
A mixture of 6.00 g of 2-bromo-N-(1-methylhexyl)propionamide and sodium hydrogen carbonate was stirred at 160° C. for 2.5 hours, cooled to room temperature, added with 30 ml of ethyl acetate, washed with water, and dried with mirabilite. Silica gel thin layer chromatography (developing solvent: ethyl acetate-n-hexane 1:2) of this product showed R f 0.33.
and 0.28 showed two types of products. After distilling off the solvent, the residue was separated using a silica gel column (developing solvent: chloroform), and the compounds listed in Table 1 (No.
0.92 g (No. 77, with high R f value), 0.93 g (No. 78, with low R f value) and 0.90 g of their mixture were obtained. Example 6 Preparation of N-[5-[1-(allylcarbamoyl)propyl]amino-4-chloro-2-fluorophenyl]-3,4,5,6-tetrahydrophthalimide N-(5-amino-4 A mixture of 2.77 g of -chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide, 4.12 g of N-allyl-2-bromobutyric acid amide, and 1.01 g of sodium hydrogen carbonate was stirred at 150°C for 2 hours. After that, the mixture was cooled to room temperature, 0 ml of ethyl acetate was added, washed with water, dried with sodium sulfate, and the solvent was distilled off. The residue was purified using a silica gel column (developing solvent system: ethyl acetate-n-hexane 1:2) and shown in Table 1.
2.30 g of the described compound (No. 175) was obtained. Example 7 N-[4-chloro-3-[1-(2-methylbutylcarbamoyl)propyl]aminophenyl]
-Production of 3,4,5,6-tetrahydrophthalimide N-(3-amino-4-chlorophenyl)-3,
2.77g of 4,5,6-tetrahydrophthalimide,
N-(2-methylbutyl)-2-bromobutyric acid amide
4.60g, sodium bicarbonate 1.01g, potassium iodide
A mixture of 0.38 g and 5 ml of sulfolane was stirred at 160° C. for 3 hours, cooled to room temperature, added with 30 ml of ethyl acetate, washed with water, dried with sodium sulfate, and then the solvent was distilled off. The residue was purified using a silica gel column (developing solvent: ethyl acetate-n-hexane 1:3) to produce the compounds listed in Table 1 (No.
166) Obtained 1.90g. Example 8 N-[2,4-dibromo-5-fluoro3-[1
-(1-methylpropyl)carbamoylethyl]
Production of aminophenyl]-3,4,5,6-tetrahydrophthalimide N-[2-fluoro-5-[1-(1-methylpropyl)carbamoylethyl]aminophenyl]
-3,4,5,6-tetrahydrophthalimide
1.60 g of bromine was added dropwise to a solution of 1.93 g and 5 ml of acetic acid at room temperature with stirring. After 0.5 hours ethyl acetate 20
After washing with water and drying the solution with sodium sulfate, the solvent was distilled off. The residue was purified using a silica gel column (developing solvent: ethyl acetate-n-hexane 1:1) to obtain 3.10 g of the compound (No. 55) listed in Table 1. Example 9 N-[2-chloro-3-(1-ethoxycarbonylpropyl)amino-6-fluorophenyl]
-Production of 3,4,5,6-tetrahydrophthalimide N-[5-(1-ethoxycarbonylpropyl)
Amino-2-fluorophenyl]-3,4,5,
0.70 g of sulfuryl chloride was added dropwise to a stirred solution of 1.87 g of 6-tetrahydrophthalimide and 20 ml of benzene at 10°C. After 1 hour, the solvent was distilled off and the residue was purified using a silica gel column (developing solvent: ethyl acetate-n-hexane 1:2) to obtain 0.95 g of the compound (No. 135) listed in Table 1. Example 10 N-[3-(1-carboxyethyl)amino-4
Preparation of -methylphenyl]-3,4,5,6-tetrahydrophthalimide N-[3-(1-ethoxycarbonylethyl)amino-4-methylphenyl]-3,4,5,6-
A mixture of 24.0 g of tetrahydrophthalimide, 8.9 g of sodium hydroxide, 15 ml of water and 80 ml of methanol was stirred at 80° C. for 1 hour, and then the solvent was distilled off. Cyclohexene-1,2-dicarboxylic anhydride in the residue
After adding 2.1 g and 80 ml of acetic acid and heating under reflux for 3 hours with stirring, the solvent was distilled off again, and 120 ml of ethyl acetate was added.
After washing with water and drying the solution with sodium sulfate, the solvent was distilled off. The residue was recrystallized from ethyl acetate-n-hexane to obtain 15.7 g of the compound (No. 9) listed in Table 1. Example 11 N-[4-chloro-3-[1-(N-methoxy-
Production of N-methylcarbamoyl)butyl]aminophenyl]-3,4,5,6-tetrahydrophthalimide N-[4-chloro-3-(1-carboxybutyl)aminophenyl]-3,4,5,6-tetrahydrophthalimide A solution of 0.65 g of thionyl chloride dissolved in 1 ml of dichloromethane was added dropwise to a mixture of 1.88 g of thionyl chloride, 0.99 g of pyridine, and 15 ml of dichloromethane at 7°C with stirring, and the mixture was stirred for 20 minutes. To this, 0.39 g of N,O-dimethylhydroxylamine,
Triethylamine 0.56g and dichloromethane 3
ml of the mixture was added dropwise, and after further stirring at room temperature for 1.5 hours, the reaction solution was washed successively with 2N hydrochloric acid and water.
After drying the organic layer with sodium sulfate, the solvent was distilled off, and the residue was purified using a silica gel column (developing solvent: ethyl acetate-n-hexane 4:7) to form the compounds listed in Table 1 (No.
208) Obtained 1.85g. Example 12 Preparation of N-[4-chloro-3-[1-(1-ethoxycarbonylbutyloxycarbonyl)ethyl]aminophenyl]-3,4,5,6-tetrahydrophthalimide N-[4-chloro-3- A mixture of 1.74 g of (1-carboxyethyl)aminophenyl]-3,4,5,6-tetrahydrophthalimide, 1.15 g of 2-bromovaleric acid ethyl ester, 0.64 g of potassium fluoride, and 10 ml of acetonitrile was heated under reflux for 30 hours with stirring. After that, the solvent was distilled off. Add 20 ethyl acetate to this
ml was added, washed with water, dried repeatedly with sodium sulfate, the solvent was distilled off, and the residue was transferred to a silica gel column (developing solvent: ethyl acetate-n-
Hexane 4:7) was used to purify the compound listed in Table 1 (No.
25) Obtained 1.85g. Example 13 N-[4-chloro-3-(N-ethoxycarbonyl-N-propyl)aminophenyl]-3,4,
Production of 5,6-tetrahydrophthalimide N-(4-chloro-3-propylaminophenyl)-3,4,5,6-tetrahydrophthalimide 1.50g, ethyl chlorocarbonate 0.56g, pyridine 0.45g
A mixture of 20 ml of anhydrous tetrahydrofuran and 20 ml of anhydrous tetrahydrofuran was heated under reflux for 2 hours with stirring, and then the solvent was distilled off. The residue was extracted with ethyl acetate, washed with water, dried with sodium sulfate, and then the solvent was distilled off. The residue was purified with a silica gel column (developing solvent: ethyl acetate-n-hexane 1:3) to obtain the compounds listed in Table 1. (No.243) 1.25g was obtained. Example 16 N-[4-chloro-3-(N-methoxy-N-methylcarbamoyl)aminophenyl]-3,4,
Production of 5,6-tetrahydrophthalimide N-(3-amino-4-chlorophenyl)-3,
2.77g of 4,5,6-tetrahydrophthalimide,
N-methoxy-N-methylcarbamoyl chloride
A mixture of 1.19 g and 10 ml of pyridine at room temperature
After standing for a period of time, 30 ml of water was added. The precipitated crystals were collected, washed with water, dried, and recrystallized from ethyl acetate-n-hexane to obtain 1.99 g of the compound (No. 265) listed in Table 1. Other compounds included in the above general formula were also prepared by any of the methods described above. The manufacturing method is shown in the Example No. column of Table 1 below. All the compounds listed in Table 1 were confirmed by IR spectrum and/or 1 H-NMR spectrum.
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【表】
製剤例 １
水和剤の製造法
表１記載の化合物または比較剤50部（以下の部
は全て重量部を示す。）、白土カープレツクス＃80
（塩野義製薬社商標）15部、Ｎ，Ｎカオリンクレ
ー（土屋カオリン社商標）30部および高級アルコ
ール硫酸エステス系界面活性剤ソルボール8070
（東邦化学社商標）５部を配合し、均一に混合粉
砕して有効成分50％を含有する水和剤を得た。
製剤例 ２
粒剤の製造法
表１記載の化合物または比較剤５部（以下の部
は全て重量部を示す。）、クレー（日本タルク社
製）38部、ベントナイト（豊順洋行社製）55部、
サクシネート系界面活性剤エヤロールCT−１（東
邦化学社商標）２部を混合し、更に水を加えて練
り合せ、造粒機を用いて造粒する。次いで、これ
を60℃で２時間乾燥し、有効成分５％を含有する
粒剤を得た。
製剤例 ３
乳剤の製造法
表１記載の化合物または比較剤30部（以下の部
は全て重量部を示す。）をキシレン30部とジメチ
ルホルムアミド25部からなる混合溶媒に溶解し、
更にポリオキシエチレン系界面活性剤ソルポール
3005X（東邦化学社商標）15部を加えて有効成分
30％を含有する乳剤を得た。
実施例 17
畑地土壌処理試験
2500分の１アールの樹脂性バツトに、畑地黒ぼ
く土壌を充填し、施肥後、トウモロコシ、コム
ギ、オオムギの各種子を播種して、2.5cmの覆土
を行なつた。
この土壌表層内に、表２に示した各種雑草種子
を混合した後、製剤例１に準じて調製した各薬剤
の水和剤および比較剤として、３−（3′，4′−ジ
クロルフエニル）−１−メトキシ−１−メチルウ
レア（以下比較剤Ａと略記する。）、２，４−ジク
ロルフエニル−4′−ニトロフエニルエーテル（以
下比較剤Ｂと略記する。）またはＮ−メトキシメ
チル−２，６−ジエチル−α−クロルアセトアニ
リド（以下比較剤Ｃと略記する。）を有効成分と
する水和剤または乳剤を水で希釈調整し、有効成
分量が、１アール当り3.125、6.25、12.5、25gと
なる様に土壌表面に小型動力加圧噴霧機で均一に
散布した。薬剤散布後30日目に除草効果の調査を
行い、同時に各作物に対する薬害についても調査
を行なつた。その結果を表２に示す。
尚、除草力の評価は
（１−処理区における雑草の地上部生体重
／無処理区における雑草の地上部生体重）×100＝Ｙ（
％）
を求め下記の基準による除草効果係数で表わし
た。[Table] Formulation example 1 Manufacturing method of wettable powder 50 parts of the compound listed in Table 1 or comparative agent (all parts below indicate parts by weight), White Clay Carplex #80
(Shionogi & Co., Ltd. trademark) 15 parts, N,N kaolin clay (Tsuchiya Kaolin Co., Ltd. trademark) 30 parts and higher alcohol sulfate Esthes surfactant Solbol 8070
(Trademark of Toho Chemical Co., Ltd.) 5 parts were mixed and pulverized uniformly to obtain a wettable powder containing 50% of the active ingredient. Formulation example 2 Manufacturing method of granules 5 parts of the compound listed in Table 1 or comparative agent (all parts below indicate parts by weight), 38 parts of clay (manufactured by Nippon Talc Co., Ltd.), 55 parts of bentonite (manufactured by Hojun Yoko Co., Ltd.) Department,
Two parts of the succinate surfactant Airol CT-1 (trademark of Toho Chemical Co., Ltd.) are mixed, water is added, the mixture is kneaded, and the mixture is granulated using a granulator. Next, this was dried at 60° C. for 2 hours to obtain granules containing 5% of the active ingredient. Formulation Example 3 Emulsion Manufacturing Method 30 parts of the compound listed in Table 1 or the comparative agent (all parts below indicate parts by weight) were dissolved in a mixed solvent consisting of 30 parts of xylene and 25 parts of dimethylformamide,
Furthermore, the polyoxyethylene surfactant Solpol
Add 15 parts of 3005X (trademark of Toho Chemical Co., Ltd.) to the active ingredient
An emulsion containing 30% was obtained. Example 17 Upland soil treatment test A 1/2500 are resin vat was filled with upland Kuroboku soil, and after fertilization, each seed of corn, wheat, and barley was sown and covered with 2.5 cm of soil. . After mixing various weed seeds shown in Table 2 into the soil surface layer, 3-(3',4'-dichlorophenyl)- 1-methoxy-1-methylurea (hereinafter abbreviated as comparative agent A), 2,4-dichlorophenyl-4'-nitrophenyl ether (hereinafter abbreviated as comparative agent B) or N-methoxymethyl-2,6 - A wettable powder or emulsion containing diethyl-α-chloroacetanilide (hereinafter abbreviated as Comparative Agent C) as an active ingredient was diluted with water, and the amount of active ingredient was 3.125, 6.25, 12.5, and 25g per are. It was evenly spread over the soil surface using a small powered pressurized sprayer. The herbicidal effect was investigated 30 days after the chemical was sprayed, and at the same time, the chemical damage to each crop was also investigated. The results are shown in Table 2. In addition, the evaluation of herbicidal power is (1 - above-ground fresh weight of weeds in treated area / above-ground fresh weight of weeds in non-treated area) x 100 = Y (
%) was determined and expressed as a herbicidal effectiveness coefficient based on the following criteria.
【表】【table】
【表】
尚、薬害の評価は、
（１−処理区における作物の地上部生体重
／無処理区における作物の地上部生体重）×100＝Ｙ（
％）
を求め、下記の基準による薬害係数で表わした。[Table] In addition, the evaluation of chemical damage is as follows: (1 - above-ground fresh weight of crops in treated area / above-ground fresh weight of crops in non-treated area) x 100 = Y (
%) was calculated and expressed as a drug toxicity coefficient according to the following criteria.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
実施例 18
茎葉処理試験
小型ポリエチレン製ポツトに畑地黒ぼく土壌を
充填し施肥後、食用ビエ、メヒシバ、ダイコン、
イヌタデ、コムギ、トウモロコシ、イネの種子を
播種した。温室内で栽培管理を続け、供試植物の
生育程度が、食用ビエは２葉期、メヒシバは３葉
期、ダイコンは第１本葉期、イヌタデは2.5葉期、
コムギは２葉期、トウモロコシは2.5葉期、イネ
は３葉期に達した時、製剤例３に準じて調製した
各薬剤の乳剤および比較剤３，４−ジクロルプロ
ピオン酸アニリド（以下比較剤Ｄと略記する。）
を有効成分とする乳剤を水で希釈調整し、有効成
分濃度が0.0625、0.125、0.25％となる様にして得
られた各調製液を１アール当り、10リツトルの液
量となる様に小型動力加圧噴霧機で散布処理を行
なつた。
その後、温室内で観察を続け、薬剤散布後15日
目に除草効果および薬害の調査を行なつた。その
結果を表３に示す。
尚、除草力および薬害の評価については試験例
１と同様に表わした。[Table] Example 18 Stem and leaf treatment test After filling small polyethylene pots with upland black soil and fertilizing, edible millet, crabgrass, radish,
Seeds of Japanese knotweed, wheat, corn, and rice were sown. Cultivation management continued in the greenhouse, and the growth levels of the test plants were as follows: edible millet at the 2-leaf stage, crabgrass at the 3-leaf stage, radish at the 1st true leaf stage, Japanese knotweed at the 2.5-leaf stage,
When wheat reached the 2-leaf stage, corn the 2.5-leaf stage, and rice the 3-leaf stage, the emulsion of each drug prepared according to Formulation Example 3 and the comparative agent 3,4-dichloropropionic acid anilide (hereinafter referred to as the comparative agent) (Abbreviated as D)
The emulsion containing the active ingredient is diluted with water, and each prepared liquid obtained by adjusting the active ingredient concentration to 0.0625, 0.125, and 0.25% is heated using a small power source so that the liquid volume is 10 liters per are. Spraying treatment was carried out using a pressurized sprayer. Afterwards, observations were continued in the greenhouse, and on the 15th day after spraying, we investigated herbicidal effects and chemical damage. The results are shown in Table 3. The evaluation of herbicidal power and phytotoxicity was expressed in the same manner as in Test Example 1.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
実施例 19
水田雑草発生前湛水土壌処理試験
2500分の１アールのバツトに水田沖積埴壌土を
充填し、施肥後、タイヌビエ、キカシグサ、ホタ
ルイ、ヘラオモダカの各種子を播種した。
一方、３葉期の水稲苗（品種：ササニシキ、草
丈：15cm、苗質：良）をポツト当り２本２株で挿
入後約２cmの浅植えを行つた。３cmの水深を保
ち、移植後翌日に製剤例２に準じて調製した粒剤
およびＳ−（４−クロルベンジル）−Ｎ，Ｎ−ジエ
チル−チオールカーバメイト（以下比較剤Ｅと略
記する。）を有効成分とする粒剤を、有効成分量
として１アール当り6.25、12.5、25gとなる様に
所定量湛水面に落下させた。処理後３日間３cm／
日の減水深を与え、その後温室内で管理し、薬剤
処理後21日目に除草効果および薬害の調査を行な
つた。
その結果を表４に示す。
尚、除草力および薬害の評価は試験例１の基準
と同様に表わした。[Table] Example 19 Flooded soil treatment test before weed emergence in paddy fields Paddy alluvial clay loam was filled in a 1/2500 are vat, and after fertilization, seeds of Japanese millet, Kikashigusa, Firefly, and Helaomodaka were sown. On the other hand, 3-leaf stage paddy rice seedlings (variety: Sasanishiki, plant height: 15 cm, seedling quality: good) were inserted into each pot with 2 plants and then planted at a shallow depth of approximately 2 cm. A water depth of 3 cm was maintained, and the next day after transplantation, granules prepared according to Formulation Example 2 and S-(4-chlorobenzyl)-N,N-diethyl-thiol carbamate (hereinafter abbreviated as Comparative Agent E) were added. Predetermined amounts of granules as ingredients were dropped onto the flooded surface so that the amount of active ingredient was 6.25, 12.5, and 25 g per are. 3cm/3 days after treatment
After that, the plants were kept in a greenhouse, and the herbicidal effects and damage were investigated on the 21st day after the chemical treatment. The results are shown in Table 4. The evaluation of herbicidal power and phytotoxicity was expressed in the same manner as in Test Example 1.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
Claims (1)
メトキシ基を示し、ＹおよびＺは互いに同一また
は相異なる水素原子またはハロゲン原子を示す。 ＵおよびＶは互いに同一または相異なる水素原
子：【式】で表わされる基：ハロゲン 原子、アルコキシ基、シアノ基およびハロゲン原
子で置換されていてもよいアリール基から選ばれ
る置換基で置換されていてもよいアルキル基：ア
ルコキシカルボニル基またはシアノ基で置換され
ていてもよいアルケニル基：アルキニル基： 【式】で表わされる基またはアルキルスルホ ニル基を示す。 上記置換基中、 R1は水素原子、アルキル基またはフエニル基
を示し、R2は水素原子またはメチル基を示し、
ｎは１〜６の整数を示す。 Ｂは−OR3、−SR4、または【式】で表わさ れる基を示す。 Ｅは水素原子、R7、OR8、SR9または
【式】で表わされる基を示す。 上記置換基中、 R3は水素原子、アルキル基、アルケニル基、
アルキニル基、シクロアルキル基、アリール基、
アラルキル基または【式】で表わされる 基を示す。 R4はアルキル基を示す。 R5およびR6は互いに同一または相異なる水素
原子、アルキル基、アルコキシ基、アルコキシア
ルキル基、アルケニル基、アルキニル基、アリー
ル基、アラルキル基、シクロアルキル基、アルキ
ルスルホニル基または【式】で表わされ る基を示すか、またはR5およびR6は式中の窒素
原子とともに酸素原子を含んでいてもよい複素環
基を示す。 R7はハロゲン原子で置換されていてもよいア
ルキル基：アルケニル基またはハロゲン原子で置
換されていてもよいアリール基を示す。 R8はアルキル基、シクロアルキル基、アラル
キル基またはアリール基を示す。 R9はアルキル基またはアリール基を示す。 R10およびR11は同一または相異なるアルキル
基、アルコキシ基またはハロゲンで置換されてい
てもよいアリール基を示す。 上記置換基中、 R12は水素原子またはアルキル基を示す。 Ｄは水酸基：アルコキシ基：または１個乃至２
個のアルキル基またはアルケニル基で置換されて
いてもよいアミノ基を示す。 但し、Ｘが塩素原子を表わし、かつＹおよびＺ
が同時に水素原子を表わすとき、ＵおよびＶが下
記表に示される組合せを表わすことはない。 【表】 【表】 で表わされるテトラヒドロフタルイミド類。 ２ 一般式 式中Ａ、Ｘ、Ｙ、Ｚ、R1、R2、ｎおよびＢは
前記と同義を示し、Ｖは水素原子、アルキル基、
【式】（式中、R7はハロゲン原子で置換され ていてもよいアルキル基を示す）で表わされる基
または【式】（式中、R8はアルキル基を示 す）で表わされる基を示す。 で表わされる特許請求の範囲第１項記載のテトラ
ヒドロフタルイミド類。 ３ 一般式 式中、Ｕはハロゲン原子、アルコキシ基、シア
ノ基およびハロゲン原子で置換されていてもよい
アリール基から選ばれる置換基で置換されていて
もよいアルキル基：アルコキシカルボニル基また
はシアノ基で置換されていてもよいアルケニル
基：アルキニル基：【式】（式中、Ｅは前記 と同義を示す）で表わされる基またはアルキルス
ルホニル基を示し、Ｖは水素原子またはアルキル
基を示す。 で表わされる特許請求の範囲第１項記載のテトラ
ヒドロフタルイミド類。 ４ 一般式 式中、Ｕはアルコキシ基またはシアノ基で置換
されていてもよいアルキル基、アルケニル基また
はアルキニル基を示し、Ｖは水素原子またはアル
キル基を示す。 で表わされる特許請求の範囲第１項記載のテトラ
ヒドロフタルイミド類。 ５ 一般式 式中、Ｕは【式】（式中、R8は前記と同 義を示す）で表わされる基または【式】 （式中、R9は前記と同義を示す）で表わされる基
を示し、Ｖはアルキル基を示す。 で表わされる特許請求の範囲第１項記載のテトラ
ヒドロフタルイミド類。 ６ 一般式 式中、Ａ、Ｘ、ＹおよびＺは前記と同義を示
す。 で表わされる特許請求の範囲第１項記載のテトラ
ヒドロフタルイミド類。 ７ 一般式 式中、 Ａは水素原子またはメチル基を示す。 Ｘは水素原子、ハロゲン原子、メチル基または
メトキシ基を示し、ＹおよびＺは互いに同一また
は相異なる水素原子またはハロゲン原子を示す。 ＵおよびＶは互いに同一または相異なる水素原
子：【式】で表わされる基：ハロゲン 原子、アルコキシ基、シアノ基およびハロゲン原
子で置換されていてもよいアリール基から選ばれ
る置換基で置換されていてもよいアルキル基：ア
ルコキシカルボニル基またはシアノ基で置換され
ていてもよいアルケニル基：アルキニル基： 【式】で表わされる基またはアルキルスルホ ニル基を示す。 上記置換基中、 R1は水素原子、アルキル基またはフエニル基
を示し、R2は水素原子またはメチル基を示し、
ｎは１〜６の整数を示す。 Ｂは−OR3、−SR4、または【式】で表わさ れる基を示す。 Ｅは水素原子、R7、OR8、SR9または
【式】で表わされる基を示す。 上記置換基中、 R3は水素原子、アルキル基、アルケニル基、
アルキニル基、シクロアルキル基、アリール基、
アラルキル基または【式】で表わされる 基を示す。 R4はアルキル基を示す。 R5およびR6は互いに同一または相異なる水素
原子、アルキル基、アルコキシ基、アルコキシア
ルキル基、アルケニル基、アルキニル基、アリー
ル基、アラルキル基、シクロアルキル基、アルキ
ルスルホニル基または【式】で表わされ る基を示すか、またはR5およびR6は式中の窒素
原子とともに酸素原子を含んでいてもよい複素環
基を示す。 R7はハロゲン原子で置換されていてもよいア
ルキル基：アルケニル基またはハロゲン原子で置
換されていてもよいアリール基を示す。 R8はアルキル基、シクロアルキル基、アラル
キル基またはアリール基を示す。 R9はアルキル基またはアリール基を示す。 R10およびR11は同一または相異なるアルキル
基、アルコキシ基またはハロゲンで置換されてい
てもよいアリール基を示す。 上記置換基中、 R12は水素原子またはアルキル基を示す。 Ｄは水酸基：アルコキシ基：または１個乃至２
個のアルキル基またはアルケニル基で置換されて
いてもよいアミノ基を示す。 但し、Ｘが塩素原子を表わし、かつＹおよびＺ
が同時に水素原子を表わすとき、ＵおよびＶが下
記表に示される組み合わせを表わすことはない。 【表】 【表】 で表わされるテトラヒドロフタルイミド類を有効
成分とする除草剤。[Claims] 1. General formula In the formula, A represents a hydrogen atom or a methyl group. X represents a hydrogen atom, a halogen atom, a methyl group or a methoxy group, and Y and Z represent hydrogen atoms or halogen atoms which are the same or different from each other. U and V are hydrogen atoms that are the same or different from each other: a group represented by the formula: substituted with a substituent selected from a halogen atom, an alkoxy group, a cyano group, and an aryl group optionally substituted with a halogen atom; Alkyl group: Alkenyl group optionally substituted with an alkoxycarbonyl group or cyano group: Alkynyl group: Indicates a group represented by the formula or an alkylsulfonyl group. In the above substituents, R 1 represents a hydrogen atom, an alkyl group or a phenyl group, R 2 represents a hydrogen atom or a methyl group,
n represents an integer of 1 to 6. B represents -OR 3 , -SR 4 or a group represented by [Formula]. E represents a hydrogen atom, R 7 , OR 8 , SR 9 or a group represented by [Formula]. Among the above substituents, R 3 is a hydrogen atom, an alkyl group, an alkenyl group,
Alkynyl group, cycloalkyl group, aryl group,
Indicates an aralkyl group or a group represented by [Formula]. R 4 represents an alkyl group. R 5 and R 6 are the same or different hydrogen atoms, alkyl groups, alkoxy groups, alkoxyalkyl groups, alkenyl groups, alkynyl groups, aryl groups, aralkyl groups, cycloalkyl groups, alkylsulfonyl groups, or represented by [Formula] R 5 and R 6 represent a heterocyclic group which may contain an oxygen atom together with the nitrogen atom in the formula. R 7 represents an alkyl group optionally substituted with a halogen atom: an alkenyl group or an aryl group optionally substituted with a halogen atom. R 8 represents an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group. R 9 represents an alkyl group or an aryl group. R 10 and R 11 represent the same or different alkyl groups, alkoxy groups, or aryl groups which may be substituted with halogen. In the above substituents, R 12 represents a hydrogen atom or an alkyl group. D is hydroxyl group: alkoxy group: or 1 to 2
represents an amino group which may be substituted with an alkyl group or an alkenyl group. However, X represents a chlorine atom, and Y and Z
When simultaneously represent a hydrogen atom, U and V do not represent the combinations shown in the table below. [Table] Tetrahydrophthalimides represented by [Table]. 2 General formula In the formula, A, X, Y, Z, R 1 , R 2 , n and B have the same meanings as above, and V is a hydrogen atom, an alkyl group,
Represents a group represented by [Formula] (in the formula, R 7 represents an alkyl group optionally substituted with a halogen atom) or a group represented by [formula] (in the formula, R 8 represents an alkyl group) . Tetrahydrophthalimide according to claim 1, which is represented by: 3 General formula In the formula, U is an alkyl group optionally substituted with a substituent selected from a halogen atom, an alkoxy group, a cyano group, and an aryl group optionally substituted with a halogen atom: an alkyl group substituted with an alkoxycarbonyl group or a cyano group. An optional alkenyl group: Alkynyl group: represents a group represented by the formula (wherein E has the same meaning as above) or an alkylsulfonyl group, and V represents a hydrogen atom or an alkyl group. Tetrahydrophthalimide according to claim 1, which is represented by: 4 General formula In the formula, U represents an alkyl group, an alkenyl group, or an alkynyl group which may be substituted with an alkoxy group or a cyano group, and V represents a hydrogen atom or an alkyl group. Tetrahydrophthalimide according to claim 1, which is represented by: 5 General formula In the formula, U represents a group represented by [formula] (in which R 8 has the same meaning as above) or a group represented by [formula] (wherein R 9 shows the same meaning as above), and V represents an alkyl group. Tetrahydrophthalimide according to claim 1, which is represented by: 6 General formula In the formula, A, X, Y and Z have the same meanings as above. Tetrahydrophthalimide according to claim 1, which is represented by: 7 General formula In the formula, A represents a hydrogen atom or a methyl group. X represents a hydrogen atom, a halogen atom, a methyl group or a methoxy group, and Y and Z represent hydrogen atoms or halogen atoms which are the same or different from each other. U and V are hydrogen atoms that are the same or different from each other: a group represented by the formula: substituted with a substituent selected from a halogen atom, an alkoxy group, a cyano group, and an aryl group optionally substituted with a halogen atom; Alkyl group: Alkenyl group optionally substituted with an alkoxycarbonyl group or cyano group: Alkynyl group: Indicates a group represented by the formula or an alkylsulfonyl group. In the above substituents, R 1 represents a hydrogen atom, an alkyl group or a phenyl group, R 2 represents a hydrogen atom or a methyl group,
n represents an integer of 1 to 6. B represents -OR 3 , -SR 4 or a group represented by [Formula]. E represents a hydrogen atom, R 7 , OR 8 , SR 9 or a group represented by [Formula]. Among the above substituents, R 3 is a hydrogen atom, an alkyl group, an alkenyl group,
Alkynyl group, cycloalkyl group, aryl group,
Indicates an aralkyl group or a group represented by [Formula]. R 4 represents an alkyl group. R 5 and R 6 are the same or different hydrogen atoms, alkyl groups, alkoxy groups, alkoxyalkyl groups, alkenyl groups, alkynyl groups, aryl groups, aralkyl groups, cycloalkyl groups, alkylsulfonyl groups, or represented by [Formula] R 5 and R 6 represent a heterocyclic group which may contain an oxygen atom together with the nitrogen atom in the formula. R 7 represents an alkyl group optionally substituted with a halogen atom: an alkenyl group or an aryl group optionally substituted with a halogen atom. R 8 represents an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group. R 9 represents an alkyl group or an aryl group. R 10 and R 11 represent the same or different alkyl groups, alkoxy groups, or aryl groups which may be substituted with halogen. In the above substituents, R 12 represents a hydrogen atom or an alkyl group. D is hydroxyl group: alkoxy group: or 1 to 2
represents an amino group which may be substituted with an alkyl group or an alkenyl group. However, X represents a chlorine atom, and Y and Z
When both represent a hydrogen atom, U and V do not represent the combinations shown in the table below. [Table] [Table] Herbicides containing tetrahydrophthalimides as active ingredients.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19984781A JPS58103363A (en) | 1981-12-11 | 1981-12-11 | Tetrahydrophthalimide and herbicide containing the same as active constituent |
| EP82109201A EP0077938A3 (en) | 1981-10-23 | 1982-10-05 | N-(3-substituted aminophenyl) tetrahydrophthalimides and herbicidal composition |
| AU89463/82A AU8946382A (en) | 1981-10-23 | 1982-10-18 | N-(3-substituted amino phenyl) tetra hydrophthalimides |
| IL67025A IL67025A0 (en) | 1981-10-23 | 1982-10-20 | N-(3-substituted aminophenyl)tetrahydrophthalimides and herbicidal composition |
| BR8206186A BR8206186A (en) | 1981-10-23 | 1982-10-22 | TETRAHYDROFTALIMID, HERBICIDE COMPOSITION, PROCESS FOR THE PRODUCTION OF A TETRAHYDROFTALIMID AND PROCESS FOR CONTROL OF UNDESIRABLE WEEDS |
| ES516765A ES8401031A1 (en) | 1981-10-23 | 1982-10-22 | N-(3-substituted aminophenyl) tetrahydrophthalimides and herbicidal composition. |
| DK470082A DK470082A (en) | 1981-10-23 | 1982-10-22 | TETRAHYDROPHTHALIMIDES, METHOD OF PREPARING IT AND USING ITS ACTIVE INGREDIENT IN HERBICIDES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19984781A JPS58103363A (en) | 1981-12-11 | 1981-12-11 | Tetrahydrophthalimide and herbicide containing the same as active constituent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58103363A JPS58103363A (en) | 1983-06-20 |
| JPH0257543B2 true JPH0257543B2 (en) | 1990-12-05 |
Family
ID=16414633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19984781A Granted JPS58103363A (en) | 1981-10-23 | 1981-12-11 | Tetrahydrophthalimide and herbicide containing the same as active constituent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58103363A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03169859A (en) * | 1982-10-29 | 1991-07-23 | Sumitomo Chem Co Ltd | N-phenyltetrahydrophthalimide derivative and herbicide containing the same as active ingredient |
| JPS5980661A (en) * | 1982-10-29 | 1984-05-10 | Sumitomo Chem Co Ltd | N-phenyltetrahydrophthalimide derivative, its preparation and herbicide containing the same as active constituent |
| JPS59181256A (en) * | 1983-03-30 | 1984-10-15 | Sumitomo Chem Co Ltd | 2h-4,5,6,7-tetrahydro-isoindole-1,3-dione derivative, its preparation, and herbicide containing it as active ingredient |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5813567A (en) * | 1981-06-29 | 1983-01-26 | ロ−ム・アンド・ハ−ス・コンパニ− | Substituted phthalimide compound and herbicidal composition |
-
1981
- 1981-12-11 JP JP19984781A patent/JPS58103363A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5813567A (en) * | 1981-06-29 | 1983-01-26 | ロ−ム・アンド・ハ−ス・コンパニ− | Substituted phthalimide compound and herbicidal composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58103363A (en) | 1983-06-20 |
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