JPH0245621B2 - TETORAHIDOROFUTARUIMIDORUIOYOBIKOREOJUKOSEIBUNTOSURUJOSOZAI - Google Patents
TETORAHIDOROFUTARUIMIDORUIOYOBIKOREOJUKOSEIBUNTOSURUJOSOZAIInfo
- Publication number
- JPH0245621B2 JPH0245621B2 JP14007680A JP14007680A JPH0245621B2 JP H0245621 B2 JPH0245621 B2 JP H0245621B2 JP 14007680 A JP14007680 A JP 14007680A JP 14007680 A JP14007680 A JP 14007680A JP H0245621 B2 JPH0245621 B2 JP H0245621B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- hydrogen atom
- phenyl
- methyl
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 230000002363 herbicidal effect Effects 0.000 claims description 25
- 239000004480 active ingredient Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000004009 herbicide Substances 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 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 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 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 3
- -1 n-octyl group Chemical group 0.000 description 104
- 150000001875 compounds Chemical class 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000004927 clay Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000003136 n-heptyl 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])* 0.000 description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000234653 Cyperus Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- 235000003270 potassium fluoride Nutrition 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 3
- 240000003176 Digitaria ciliaris Species 0.000 description 3
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 3
- 235000005476 Digitaria cruciata Nutrition 0.000 description 3
- 235000006830 Digitaria didactyla Nutrition 0.000 description 3
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
- 240000003173 Drymaria cordata Species 0.000 description 3
- 235000014716 Eleusine indica Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 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
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 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
- 239000000969 carrier Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-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
- LSOUNTYMFZHTCD-UHFFFAOYSA-N 2-[2-bromo-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)phenoxy]propanoic acid Chemical compound C1=C(Br)C(OC(C)C(O)=O)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 LSOUNTYMFZHTCD-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 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 2
- 240000004731 Acer pseudoplatanus Species 0.000 description 2
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000254158 Lampyridae Species 0.000 description 2
- 240000000486 Lepidium draba Species 0.000 description 2
- 235000000391 Lepidium draba Nutrition 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 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
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 235000006485 Platanus occidentalis Nutrition 0.000 description 2
- 244000292697 Polygonum aviculare Species 0.000 description 2
- 235000006386 Polygonum aviculare Nutrition 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- 235000006140 Raphanus sativus var sativus Nutrition 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
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 125000005998 bromoethyl group Chemical group 0.000 description 2
- 125000004799 bromophenyl group Chemical group 0.000 description 2
- 125000006226 butoxyethyl group Chemical group 0.000 description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000006003 dichloroethyl group Chemical group 0.000 description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 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
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
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- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 125000006000 trichloroethyl group Chemical group 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-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
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical group CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
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- ZQXWTERAJPSRBP-UHFFFAOYSA-N 2-(4-bromo-3-methoxyphenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Br)C(OC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 ZQXWTERAJPSRBP-UHFFFAOYSA-N 0.000 description 1
- OHPXGBJJBLZLJS-UHFFFAOYSA-N 2-(4-chloro-3-methoxyphenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Cl)C(OC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 OHPXGBJJBLZLJS-UHFFFAOYSA-N 0.000 description 1
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- AFJWMGOTLUUGHF-UHFFFAOYSA-N 4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1CCCC2=C1C(=O)NC2=O AFJWMGOTLUUGHF-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
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
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- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
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- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- 235000005205 Pinus Nutrition 0.000 description 1
- 241000218602 Pinus <genus> Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
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- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
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- 239000012752 auxiliary agent Substances 0.000 description 1
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- NEDMOHHWRPHBAL-UHFFFAOYSA-N benzyl pyrrolidin-1-ium-2-carboxylate;chloride Chemical compound Cl.C1CCNC1C(=O)OCC1=CC=CC=C1 NEDMOHHWRPHBAL-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
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- 235000006263 bur ragweed Nutrition 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical group CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 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
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 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
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- 239000012320 chlorinating reagent Substances 0.000 description 1
- XQNAUQUKWRBODG-UHFFFAOYSA-N chlornitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(Cl)C=C1Cl XQNAUQUKWRBODG-UHFFFAOYSA-N 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
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- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- 238000005755 formation reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 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
- 239000002917 insecticide Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical group 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 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
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical group CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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- 229920000573 polyethylene Polymers 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical group C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
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- 125000005270 trialkylamine group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical group CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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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）により殺草活
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を予知することは困
難である。
本発明者らは、テトラヒドロフタルイミド類を
有効成分とする除草剤について鋭意研究した結
果、Ｎ置換アリールが、２位に水素またはハロゲ
ン、４位にハロゲンまたは水素を有し、かつ５位
に特定の置換基を有するフエニル基である新規な
Ｎ―アリール―3.4，５，６―テトラヒドロフタ
ルイミド類が極めて優れた除草活性を示すことを
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、Ｘ，Ｙは水素原子またはハロゲン原子
を示し；Ａは
The present invention relates to novel tetrahydrophthalimides and herbicides containing them as active ingredients. Conventionally, N-aryl-3,4,5,6-tetrahydrophthalimides are known to have excellent herbicidal activity, but slight modifications to these structures (type, number, position, etc. of substituents) In many cases, the presence or absence of herbicidal activity, strength, or selectivity of herbicidal activity differs significantly depending on the compound, and it is difficult to predict the herbicidal activity of a new compound based on mere chemical structural similarity. As a result of intensive research on herbicides containing tetrahydrophthalimides as active ingredients, the present inventors found that N-substituted aryl has hydrogen or halogen at the 2-position, halogen or hydrogen at the 4-position, and a specific type of herbicide at the 5-position. It was discovered that novel N-aryl-3,4,5,6-tetrahydrophthalimides, which are phenyl groups having a substituent, exhibit extremely excellent herbicidal activity, and the present invention was achieved. That is, the gist of the present invention is the general formula [In the formula, X and Y represent hydrogen atoms or halogen atoms; A is
【式】（式中、R1は水素原
子、アルキル基、または、ハロゲン原子で置換さ
れていてもよいフエニル基を示し、R2は水素原
子または低級アルキル基を示し、ｎは１〜３の整
数を示す）、[Formula] (wherein, R 1 represents a hydrogen atom, an alkyl group, or a phenyl group optionally substituted with a halogen atom, R 2 represents a hydrogen atom or a lower alkyl group, and n represents 1 to 3 indicating an integer),
【式】または、―CH2CH＝
CH―を示し、；Ｂは―OR3（式中、R3は水素原
子、アルキル基、アルケニル基、炭素数３〜４の
アルキニル基、ハロアルキル基、ハロアルケニル
基、シアノアルキル基、ヒドロキシアルキル基、
アルコキシアルキル基、アルコキシアルコキシア
ルキル基、アルコキシアルコキシアルコキシアル
キル基、アルキルチオアルキル基、シクロアルキ
ル基、アラルキル基、フエニル基または、メチル
基で置換されていてもよいγ―ブチロラクトン
基、または、アルカリ金属、アルカリ土金属、お
よび、アルキル基で置換されていてもよいアンモ
ニウム基から選ばれる塩形成残基を示す）、―
SR4（中、R4はアルキル基、アルコキシカルボニ
ルアルキル基またはベンジル基を示す）、
[Formula] or -CH 2 CH= CH-; B is -OR 3 (wherein R 3 is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group having 3 to 4 carbon atoms, a haloalkyl group, a halo alkenyl group, cyanoalkyl group, hydroxyalkyl group,
Alkoxyalkyl group, alkoxyalkoxyalkyl group, alkoxyalkoxyalkoxyalkyl group, alkylthioalkyl group, cycloalkyl group, aralkyl group, phenyl group, or γ-butyrolactone group optionally substituted with methyl group, or alkali metal, alkali represents a salt-forming residue selected from earth metals and ammonium groups optionally substituted with alkyl groups), -
SR 4 (in which R 4 represents an alkyl group, an alkoxycarbonylalkyl group or a benzyl group),
【式】（式中、R5は水素原子ま
たはメチル基を示し、R6はメチル基またはフエ
ニル基を示し、ｍは１から３の整数を示す）を示
す。〕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存する。
次に本発明を具体的に説明する。
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。
前記一般式（）において、化合物の除草活性
を考慮した場合、Ｘ，Ｙ，ＡおよびＢが次の様な
ものが好適に使用される。
即ち、Ｘは塩素原子、臭素原子、沃素原子また
は水素原子、好ましくは塩素原子、臭素原子また
は水素原子を表わし、Ｙは水素原子、弗素原子ま
たは塩素原子、好ましくは水素原子または塩素原
子を表わし、特に好ましくは、Ｙが水素原子のと
きＸは塩素原子、臭素原子または水素原子、Ｙが
塩素原子のときＸは塩素原子を表わす。
Ａは[Formula] (wherein R 5 represents a hydrogen atom or a methyl group, R 6 represents a methyl group or a phenyl group, and m represents an integer from 1 to 3). ] Tetrahydrophthalimides and herbicides containing them as active ingredients. Next, the present invention will be specifically explained. The tetrahydrophthalimide used as a herbicide in the present invention is represented by the above general formula (). In the general formula (), when considering the herbicidal activity of the compound, the following compounds are preferably used for X, Y, A and B. That is, X represents a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom, preferably a chlorine atom, a bromine atom or a hydrogen atom, and Y represents a hydrogen atom, a fluorine atom or a chlorine atom, preferably a hydrogen atom or a chlorine atom, Particularly preferably, when Y is a hydrogen atom, X represents a chlorine atom, a bromine atom or a hydrogen atom, and when Y is a chlorine atom, X represents a chlorine atom. A is
【式】（式中、R1は水素原子；メチ
ル基、エチル基、ｎ―プロピル基、イソプロピレ
ン基、ｎ―ブチル基、イソブチル基、Sec―ブチ
ル基、ｎ―ペンチル基、ｎ―ヘキシル基、ｎ―ヘ
プチル基、ｎ―オクチル基、ｎ―ノニル基または
ｎ―デシル基などの炭素数１〜10のアルキル基好
ましくはメチル基、エチル基、ｎ―プロピル、イ
ソプロピル基、ｎ―ブチル基、イソブチル基、ｎ
―ペンチル基、ｎ―ヘキシル基、またはｎ―ヘプ
チル基などの炭素数１〜７のアルキル基；フエニ
ル基；またはクロロフエニル基、ブロモフエニル
基、ジクロロフエニル基などの置換フエニル基、
好ましくはクロロフエニル基、ブロモフエニル
基、ジクロロフエニル基などの置換フエニル基を
表わし、R2は水素原子またはメチル基、エチル
基、プロピル基またはブチル基などの炭素数１〜
４のアルキル基、好ましくは水素原子またはメチ
ル基を表わす。）[Formula] (In the formula, R 1 is a hydrogen atom; methyl group, ethyl group, n-propyl group, isopropylene group, n-butyl group, isobutyl group, Sec-butyl group, n-pentyl group, n-hexyl group , an alkyl group having 1 to 10 carbon atoms such as n-heptyl group, n-octyl group, n-nonyl group or n-decyl group, preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, n
- Alkyl group having 1 to 7 carbon atoms such as pentyl group, n-hexyl group, or n-heptyl group; phenyl group; or substituted phenyl group such as chlorophenyl group, bromophenyl group, dichlorophenyl group,
Preferably, it represents a substituted phenyl group such as a chlorophenyl group, bromophenyl group, or dichlorophenyl group, and R 2 is a hydrogen atom or a group having 1 to 1 carbon atoms such as a methyl group, an ethyl group, a propyl group, or a butyl group.
4 represents an alkyl group, preferably a hydrogen atom or a methyl group. )
【式】または、―CH2CH＝CH―を表わ
し、ｎは１から３の整数を表わしく特に好ましく
はｎが１以外の整数の場合、R1およびR2は水素
原子を表わす。
Ｂは―OR3；SR4；２―オキソプロピル基、３
―オキソブチル基、４―オキソペンチル基、２―
オキソメチルプロピル基、３―オキソメチルブチ
ル基、４―オキソメチルペンチル基、フエナシル
基、３―オキソフエニルプロピル基または４―オ
キソフエニルブチル基などの炭素数３〜10の
[Formula] or represents -CH 2 CH=CH-, n represents an integer from 1 to 3, particularly preferably when n is an integer other than 1, R 1 and R 2 represent a hydrogen atom. B is -OR 3 ; SR 4 ; 2-oxopropyl group, 3
-Oxobutyl group, 4-oxopentyl group, 2-
having 3 to 10 carbon atoms such as oxomethylpropyl group, 3-oxomethylbutyl group, 4-oxomethylpentyl group, phenacyl group, 3-oxophenylpropyl group or 4-oxophenylbutyl group.
【式】（式中、R5は水素または
メチル基、R6はメチル基またはフエニル基を示
し、ｍは１から３の整数を表わす）で示される基
上記式においてR3は水素原子、メチル基、エ
チル基、ｎ―プロピル基、イソプロピル基、ｎ―
ブチル基、イソブチル基、sec―ブチル基、ｔ―
ブチル基、ｎ―ペンチル基、３―メチルブチル
基、２，２―ジメチルプロピル基、ｎ―ヘキシル
基、ｎ―ヘプチル基、ｎ―オクチル基、ｎ―ノニ
ル基、ｎ―デシル基、ｎ―ウンデシル基、または
ｎ―ドデシル基などの炭素数１〜12のアルキル基
好ましくはメチル基、エチル基、ｎ―プロピル
基、イソプロピル基、ｎ―ブチル基、イソブチル
基、sec―ブチル基、ｔ―ブチル基、ｎ―ペンチ
ル基、３―メチルブチル基、２，３―ジメチルプ
ロピル基またはｎ―ヘキシル基などの炭素数１〜
６のアルキル基；ビニル基、アリル基、メタクリ
ル基、２―ブテニル基または３―メチル―２―ブ
テニル基などの炭素数２〜５のアルケニル基好ま
しくはアリル基、メタリル基または２―ブテニル
基などの炭素数３〜４のアルケニル基；プロパル
ギル基、２―ブチニル基または１，１―ジメチル
プロパルギル基などの炭素数３〜４のアルキニル
基好ましくはプロパルギル基または２―ブチニル
基などの炭素数３〜４のアルキニル基；フルオロ
エチル基、クロロエチル基、ブロモエチル基、ヨ
ードエチル基、ジフルオロエチル基、ジクロロエ
チル基、ジブロモエチル基、トリフルオロエチル
基、トリクロロエチル基、トリブロモエチル基、
フルオロプロピル基、クロロプロピル基、ブロモ
プロピル基、ヨードプロピル基、ジフルオロプロ
ピル基、ジクロロプロピル基、ジブロモプロピル
基、トリフルオロプロピル基、トリクロロプロピ
ル基、トリブロモプロピル基、テトラフルオロプ
ロピル基、クロロブチル基、ブロモブチル基、ト
リフルオロブチル基、クロロペンチル基またはブ
ロモペンチル基などの１〜４個のハロゲンを含む
炭素数１〜５のハロアルキル基好ましくは、フル
オロエチル基、クロロエチル基、ブロモエチル
基、ジクロロエチル基、ジブロモエチル基、トリ
フルオロエチル基、トリクロロエチル基、クロロ
プロピル基、ブロモプロピル基、ジクロロプロピ
ル基、ジブロモプロピル基、テトラフルオロプロ
ピル基、クロロブチル基またはブロモブチル基な
どの１〜４個のハロゲンを含む炭素数２〜４のハ
ロアルキル基；クロロアリル基、ブロモアリル
基、ジクロロアリル基、ジブロモアリル基、トリ
クロロアリル基、トリブロモアリル基またはクロ
ロブテニル基などの１〜３個のハロゲンを含む炭
素数３〜４のハロアルケニル基、好ましくはクロ
ロアリル基、ジクロロアリル基またはトリクロロ
アリル基などの１〜３個の塩素原子を含む炭素数
３のハロアルケニル基；シアノメチル基、シアノ
エチル基またはシアノプロピル基などの炭素数２
〜４のシアノアルキル基；ヒドロキシエチル基、
ヒドロキシプロピル基またはヒドロキシブチル基
などの炭素数２〜４のヒドロキシアルキル基；メ
トキシエチル基、エトキシエチル基、プロポキシ
エチル基、ブトキシエチル基、ペンチルオキシエ
チル基、ヘキシルオキシエチル基、メトキシプロ
ピル基、エトキシプロピル基、プロポキシプロピ
ル基またはエトキシブチル基などの炭素数３〜８
のアルコキシアルキル基好ましくはメトキシエチ
ル基、エトキシエチル基、プロポキシエチル基、
ブトキシエチル基、メトキシプロピル基、エトキ
シプロピル基またはプロポキシプロピル基などの
炭素数３〜６のアルコキシアルキル基；メトキシ
エトキシエチル基、エトキシエトキシエチル基、
プロポキシエトキシエチル基、ブトキシエトキシ
エチル基、メトキシプロポキシプロピル基、エト
キシプロポキシプロピル基またはブトキシプロポ
キシプロピル基などの炭素数５〜10のアルコキシ
アルコキシアルキル基好ましくはメトキシエトキ
シエチル基、エトキシエトキシエチル基、プロポ
キシエトキシエチル基、ブトキシエトキシエチル
基またはメトキシプロポキシプロピル基などの炭
素数５〜８のアルコキシアルコキシアルキル基；
メトキシエトキシエトキシエチル基、エトキシエ
トキシエトキシエチル基、プロポキシエトキシエ
トキシエチル基、ブトキシエトキシエトキシエチ
ル基、メトキシプロポキシプロポキシプロピル
基、エトキシプロポキシプロポキシプロピル基ま
たはブトキシプロポキシプロポキシプロピル基な
どの炭素数７〜13のアルコキシアルコキシアルコ
キシアルキル基好ましくはメトキシエトキシエト
キシエチル基、エトキシ、エトキシエトキシエチ
ル基、プロポキシエトキシエトキシエチル基、ブ
トキシエトキシエトキシエチル基またはメトキシ
プロポキシプロポキシプロピル基などの炭素数７
〜10のアルコキシアルコキシアルコキシアルキル
基；メチルチオエチル基、エチルチオエチル基、
プロピルチオエチル基、ブチルチオエチル基、ペ
ンチルチオエチル基などの炭素数３〜８のアルキ
ルチオアルキル基；シクロブチル基、シクロペン
チル基、シクロヘキシル基、メチルシクロヘキシ
ル基、シクロヘプチル基またはシクロオクチル基
などの炭素数４〜８のシクロアルキル基好ましく
はシクロブチル基、シクロペンチル基、シクロヘ
キシル基またはシクロヘプチル基などの炭素数４
〜７のシクロアルキル基；ベンジル基、クロロベ
ンジル基、ブロモベンジル基、メチルベンジル
基、α―メチルベンジル基、α，α―ジメチルベ
ンジル基、フエネチル基、メチルフエネチル基ま
たはフエニルプロピル基などの炭素数７〜９のア
ラルキル基；フエニル基；メチル基で置換されて
いてもよいγ―ブチロラクトン基；またはナトリ
ウム、カリウム、カルシウムなどのアルカリ金
属、アルカリ土金属、およびアンモニウム基、メ
チルアンモニウム基、エチルアンモニウム基、プ
ロピルアンモニウム基、ブチルアンモニウム基、
ペンチルアンモニウム基、ヘキシルアンモニウム
基、ジメチルアンモニウム基、ジエチルアンモニ
ウム基、ジプロピルアンモニウム基、ジブチルア
ンモニウム基、トリメチルアンモニウム基、トリ
エチルアンモニウム基、トリプロピルアンモニウ
ム基、テトラメチルアンモニウム基、テトラエチ
ルアンモニウム基などの総炭素数４〜９のアルキ
ル基を０〜４個有するアンモニウム基から選ばれ
る塩形成残基を表わす。
また、R4はメチル基、エチル基、ｎ―プロピ
ル基、イソプロピル基、ｎ―ブチル基、イソブチ
ル基、sec―ブチル基、ｎ―ペンチル基、sec―ペ
ンチル基、ｎ―ヘキシル基、ｎ―ヘプチル基、ｎ
―オクチル基、ｎ―ノニル基、ｎ―デシル基、ｎ
―ウンデシル基またはｎ―ドデシル基などの炭素
数１〜12のアルキル基好ましくはメチル基、エチ
ル基、ｎ―プロピル基、イソプロピル基、ｎ―ブ
チル基、イソブチル基、ｎ―ペンチル基、sec―
ペンチル基、ｎ―ヘキシル基、ｎ―ヘプチル基、
ｎ―オクチル基、ｎ―ノニル基またはｎ―デシル
基などの炭素数１〜10のアルキル基；メトキシカ
ルボニルメチル基、エトキシカルボニルメチル
基、プロポキシカルボニルメチル基またはブトキ
シカルボニルメチル基などの炭素数３〜６のアル
コキシカルボニルアルキル基；またはベンジル基
を表わす。
本発明の式（）で示される化合物は、場合に
より光学異性体、Ｚ―Ｅ異性体またはジアステレ
オマーなどの各種異性体が存在し得る。それぞれ
の異性体のいずれかが存在し得るとき、多くの場
合、該異性体は全ての異性体を含有する混合物と
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、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）を用いてそれぞれの異性体を
得ることも可能である。
以下に上記各種異性体を与え得る式（）で示
される化合物の例を挙げる。
光学異性体の存在し得る例
式（）で示される化合物に包含される式(a)で
示される化合物は、R1が水素原子以外の特定の
基を示すとき、光学異性体を与える。またR1が
水素原子である場合においてＢが不斉中心を有す
る基である場合（例えば、[Formula] (wherein, R 5 is hydrogen or a methyl group, R 6 is a methyl group or a phenyl group, and m is an integer from 1 to 3) In the above formula, R 3 is a hydrogen atom or a methyl group. group, ethyl group, n-propyl group, isopropyl group, n-
Butyl group, isobutyl group, sec-butyl group, t-
Butyl group, n-pentyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group , or an alkyl group having 1 to 12 carbon atoms such as n-dodecyl group, preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 1 or more carbon atoms such as n-pentyl group, 3-methylbutyl group, 2,3-dimethylpropyl group or n-hexyl group
Alkyl group of 6; C2-5 alkenyl group such as vinyl group, allyl group, methacryl group, 2-butenyl group or 3-methyl-2-butenyl group, preferably allyl group, methallyl group or 2-butenyl group. Alkenyl group having 3 to 4 carbon atoms; an alkynyl group having 3 to 4 carbon atoms such as propargyl group, 2-butynyl group or 1,1-dimethylpropargyl group, preferably 3 to 4 carbon atoms such as propargyl group or 2-butynyl group Alkynyl group of 4; fluoroethyl group, chloroethyl group, bromoethyl group, iodoethyl group, difluoroethyl group, dichloroethyl group, dibromoethyl group, trifluoroethyl group, trichloroethyl group, tribromoethyl group,
Fluoropropyl group, chloropropyl group, bromopropyl group, iodopropyl group, difluoropropyl group, dichloropropyl group, dibromopropyl group, trifluoropropyl group, trichloropropyl group, tribromopropyl group, tetrafluoropropyl group, chlorobutyl group, A haloalkyl group having 1 to 5 carbon atoms and containing 1 to 4 halogens, such as a bromobutyl group, a trifluorobutyl group, a chloropentyl group, or a bromopentyl group, preferably a fluoroethyl group, a chloroethyl group, a bromoethyl group, a dichloroethyl group, Carbon containing 1 to 4 halogens such as dibromoethyl group, trifluoroethyl group, trichloroethyl group, chloropropyl group, bromopropyl group, dichloropropyl group, dibromopropyl group, tetrafluoropropyl group, chlorobutyl group or bromobutyl group Haloalkyl group of number 2 to 4; C3 to C4 halo containing 1 to 3 halogens such as chloroallyl group, bromoallyl group, dichloroallyl group, dibromoallyl group, trichloroallyl group, tribromoallyl group or chlorobutenyl group An alkenyl group, preferably a C3 haloalkenyl group containing 1 to 3 chlorine atoms such as a chloroallyl group, dichloroallyl group or trichloroallyl group; a C2 haloalkenyl group such as a cyanomethyl group, a cyanoethyl group or a cyanopropyl group
~4 cyanoalkyl group; hydroxyethyl group,
Hydroxyalkyl group having 2 to 4 carbon atoms such as hydroxypropyl group or hydroxybutyl group; methoxyethyl group, ethoxyethyl group, propoxyethyl group, butoxyethyl group, pentyloxyethyl group, hexyloxyethyl group, methoxypropyl group, ethoxy 3-8 carbon atoms such as propyl group, propoxypropyl group or ethoxybutyl group
an alkoxyalkyl group, preferably a methoxyethyl group, an ethoxyethyl group, a propoxyethyl group,
Alkoxyalkyl group having 3 to 6 carbon atoms such as butoxyethyl group, methoxypropyl group, ethoxypropyl group or propoxypropyl group; methoxyethoxyethyl group, ethoxyethoxyethyl group,
An alkoxyalkoxyalkyl group having 5 to 10 carbon atoms, such as propoxyethoxyethyl group, butoxyethoxyethyl group, methoxypropoxypropyl group, ethoxypropoxypropyl group, or butoxypropoxypropyl group, preferably methoxyethoxyethyl group, ethoxyethoxyethyl group, propoxyethoxy an alkoxyalkoxyalkyl group having 5 to 8 carbon atoms, such as an ethyl group, a butoxyethoxyethyl group, or a methoxypropoxypropyl group;
Alkoxy having 7 to 13 carbon atoms such as methoxyethoxyethoxyethyl group, ethoxyethoxyethoxyethyl group, propoxyethoxyethoxyethyl group, butoxyethoxyethoxyethyl group, methoxypropoxypropoxypropyl group, ethoxypropoxypropoxypropyl group or butoxypropoxypropoxypropyl group Alkoxyalkoxyalkyl group preferably has 7 carbon atoms such as methoxyethoxyethoxyethyl group, ethoxy, ethoxyethoxyethyl group, propoxyethoxyethoxyethyl group, butoxyethoxyethoxyethyl group or methoxypropoxypropoxypropyl group
~10 alkoxyalkoxyalkoxyalkyl groups; methylthioethyl group, ethylthioethyl group,
Alkylthioalkyl groups having 3 to 8 carbon atoms such as propylthioethyl group, butylthioethyl group, pentylthioethyl group; carbon number such as cyclobutyl group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group, cycloheptyl group or cyclooctyl group 4-8 cycloalkyl group, preferably 4 carbon atoms such as cyclobutyl group, cyclopentyl group, cyclohexyl group or cycloheptyl group
~7 cycloalkyl group; carbon number such as benzyl group, chlorobenzyl group, bromobenzyl group, methylbenzyl group, α-methylbenzyl group, α,α-dimethylbenzyl group, phenethyl group, methylphenethyl group or phenylpropyl group 7-9 aralkyl group; phenyl group; γ-butyrolactone group optionally substituted with methyl group; or alkali metals such as sodium, potassium, and calcium, alkaline earth metals, and ammonium, methylammonium, and ethylammonium groups , propylammonium group, butylammonium group,
Total carbon such as pentylammonium group, hexylammonium group, dimethylammonium group, diethylammonium group, dipropylammonium group, dibutylammonium group, trimethylammonium group, triethylammonium group, tripropylammonium group, tetramethylammonium group, tetraethylammonium group, etc. It represents a salt-forming residue selected from ammonium groups having 0 to 4 alkyl groups of numbers 4 to 9. In addition, R 4 is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, n-pentyl group, sec-pentyl group, n-hexyl group, n-heptyl group. base, n
-Octyl group, n-nonyl group, n-decyl group, n
-Alkyl group having 1 to 12 carbon atoms such as undecyl group or n-dodecyl group, preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, n-pentyl group, sec-
pentyl group, n-hexyl group, n-heptyl group,
Alkyl groups with 1 to 10 carbon atoms, such as n-octyl, n-nonyl, or n-decyl; 3 to 10 carbon atoms, such as methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, or butoxycarbonylmethyl 6 represents an alkoxycarbonylalkyl group; or a benzyl group. The compound represented by formula () of the present invention may exist in various isomers such as optical isomers, Z--E isomers, and diastereomers. When any of the respective isomers may be present, the isomers are often obtained as a mixture containing all isomers. These isomers can be obtained using various known methods (e.g., asymmetric synthesis, 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 isomers of Examples of compounds represented by formula () that can give the above various isomers are listed below. Possible examples of optical isomers The compound represented by formula (a) included in the compound represented by formula () gives optical isomers when R 1 represents a specific group other than a hydrogen atom. Furthermore, when R 1 is a hydrogen atom and B is a group having an asymmetric center (for example,
【式】も
光学異性体を与える。
Ｚ―Ｅ異性体の存在し得る例
式（Ｉ）で示される化合物に包含される式(b)で
示される化合物は、Ｚ―Ｅ異性体を与える。
ジアステレオマーの存在し得る例；
式（）で示される化合物に包含される式(c)で
示される化合物は、２個の不斉中心を有しており
ジアステレオマーを与える。
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。
上記反応式でＺは塩素、臭素または沃素などの
ハロゲン原子を示す。反応はアセトン、エチルメ
チルケトン、ベンゼン、トルエン、アセトニトリ
ル、テトラヒドロフラン、Ｎ，Ｎ―ジメチルホル
ムアミドなどの溶媒中、炭酸ナトリウム、炭酸カ
リウム、水酸化ナトリウム、水酸化カリウムなど
の塩基性化合物または弗化カリウム、弗化セシウ
ム、弗化テトラｎ―ブチルアンモニウムなどの弗
素化合物の存在下、沃化ナトリウム、沃化カリウ
ムなどの沃素化合物の存在下あるいは不存在下０
〜150℃で行なわれる。
テトラヒドロフタル酸無水物と上記アニリン類
との反応は、無溶媒または酢酸、トルエン、メタ
ノール、水などの溶媒中60〜200℃で行なわれる。
上記加水分解反応は、(i)水、水―メタノール、
水―エタノール、水、ジオキサンなどの溶媒中、
塩酸、硫酸などの酸の存在下０〜120℃、または
蟻酸、酢酸などの溶媒中メタンスルホン酸、ｐ―
トルエンスルホン酸の存在下80〜180℃で行なわ
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、ピリジンなどの溶媒中、水酸
化リチウム、臭素化リチウム、沃素化リチウム、
沃素化ナトリウムなどの存在下100〜200℃で行な
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
バリウムなどの存在下−20〜150℃において反応
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℃で反応する
ことにより行われる。
本反応を用いて式（）で示されるカルボン酸
類を製造する場合には原料として用いられる式
（）の化合物としては、より安価かつ容易に得
られるＢがメトキシ基またはエトキシ基であるエ
ステル類を用いるのが好ましい。
上記エステル化反応は、無溶媒下、塩化水素、
硫酸、ｐ―トルエンスルホン酸などの酸触媒の存
在下０〜100℃で行なわれる。
この反応は、無溶媒またはベンゼン、トルエ
ン、キシレンなどの溶媒中塩化チオニル、五塩化
リンなどの塩素化剤を０〜150℃で作用させ式
（）で示される酸塩化物を形成せしめ、これに
式（）で示される化合物を、無溶媒またはベン
ゼン、トルエン、テトラクロルエタン、トリクロ
ルエチレンなどの溶媒中、トリエチルアミン、ピ
リジン、Ｎ，Ｎ―ジメチルアニリン、炭酸水素ナ
トリウム、炭酸ナトリウム、炭酸カリウムなどの
塩基性化合物の存在下または不存在下−20〜130
℃で行なわれる。
本反応を用いて式（）で示される化合物を製
造する場合、式（）で示される酸塩化物を特に
単離精製する必要はなく一容器（one pot）反応
で目的物が得られる。また式（）で示される酸
塩化物の生成はそのirスペクトルを測定すること
により容易に確認できる。
上記反応式でＺは塩素、臭素、沃素などのハロ
ゲン原子、Ｂは―OR3で示される基を示す。本反
応は、アセトン、エチルメチルケトン、ベンゼ
ン、トルエン、アセトニトリル、テトラヒドロフ
ラン、Ｎ，Ｎ―ジメチルホルムアミド、塩化メチ
レン、クロロホルムなどの溶媒中、炭酸ナトリウ
ム、炭酸カリウム、金属ナトリウム、水素化ナト
リウム、弗化カリウム、弗化セシウムなどの酸結
合剤を用いて０〜150℃で行なわれる。
上記反応式でB′はＢで定義した前出の基中特
定の基を示す。本エステル交換反応は通常無溶媒
下、塩化水素、硫酸、ｐ―トルエンスルホン酸な
どの酸触媒の存在下０〜150℃にて行なわれる。
上記反応式でＺは塩素、臭素または沃素などの
ハロゲン原子を示す。反応はアセトン、エチルメ
チルケトン、ベンゼン、トルエン、アセトニトリ
ル、テトラヒドロフラン、Ｎ，Ｎ―ジメチルホル
ムアミドなどの溶媒中、炭酸ナトリウム、炭酸カ
リウム、水酸化ナトリウム、水酸化カリウムなど
の塩基性化合物の存在下、沃化ナトリウム、沃化
カリウムの存在下あるいは不存在下０〜150℃で
行なわれる。なお、本反応は下記中間体（）を
経て進行するものと考えられる。
本反応式でＢはOR3を示し、R3は塩形成残基
を示す。本塩形成反応は、水、水―メタノール、
水―エタノール、ベンゼン、トルエン、テトラヒ
ドロフランなどの溶媒中−20℃〜150℃で行なわ
れる。用いられる塩基性化合物としては、水酸化
ナトリウム、水酸化カリウム、水酸化カルシウム
などの水酸化アルカリ金属またはアルカリ土金
属、水素化ナトリウム、水素化カリウムなどの水
素化アルカリ金属、金属ナトリウム、金属カリウ
ムなどのアルカリ金属、アンモニア、モノ、ジま
たはトリアルキルアミンなどが挙げられる。
これら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担
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
て、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、土壤
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
土壤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２―80gr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
土壤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壤処理および茎葉兼
土壤処理においても、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。
本発明の除草剤は、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、例えば野生アサガオ、
ヤエムグラ、ハコベ、ハキダメギク、アカザ、シ
ロザ、イチビ、野性カラシナ、ナズナ、ギシギ
シ、タデ、スベリヒユ、イヌビユ、ブタクサ、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、例えばノビエ、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。
本発明の除草剤は、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。
双子葉植物である裁培作物：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。
単子葉植物である裁培作物：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。
本発明の除草剤の適用範囲は以上の種属の植物
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されるものではない。
実施例 １
Ｎ―〔４―ブロモ―３―（１―エトキシカルボ
ニルブチルオキシ）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―ブロモ―３―ヒドロキシフエニル）
―３，４，５，６―テトラヒドロフタルイミド
15.0gr、α―ブロモ吉草酸エチル12.0gr、炭酸カ
リウム7.7gr、沃化カリウム2.5grおよびアセトン
50mlの混合物を撹拌下に３時間加熱還流した後、
室温迄冷却し、塩を別した。液を減圧濃縮し
残留物に2N塩酸を加えて結晶を析出させた。こ
の結晶を取し、水洗、乾燥後、シリカゲルカラ
ムで酢酸エチル―ｎ―ヘキサン１：３を展開溶媒
として溶出し、表１記載の化合物（No.92）17.6gr
を得た。
実施例 ２
Ｎ―〔４―ブロモ―３―（１―エトキシカルボ
ニルエチルオキシ）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
1.52gr、４―ブロモ―３―（１―エトキシカルボ
ニルエチルオキシ）アニリン（n25 D1.5590）2.88gr
および酢酸10mlの混合物を撹拌下に２時間加熱還
流後、室温迄冷却しこれに水を加えた。析出した
結晶を取した後、ベンゼン―シクロヘキサンよ
り再結晶し表１記載の化合物（No.18）3.89grを得
た。
実施例 ３
Ｎ―〔２，４―ジクロロ―５―（１―カルボキ
シルエチルオキシ）フエニル〕―３，４，５，
６―テトラヒドロフタルイミドの製造
Ｎ―〔２，４―ジクロロ―５―（１―エトキシ
カルボニルエチルオキシ）フエニル〕―３，４，
５，６―テトラヒドロフタルイミド14.4gr、メタ
ンスルホン酸3.40gr、86％蟻酸35mlの混合物を撹
拌下に15時間加熱還流後、室温迄冷却しこれに水
を加え酢酸エチルにて抽出した。抽出液を減圧濃
縮して得られた油状物にｎ―ヘキサンを加えトリ
チユレートすると結晶が得られた。これをベンゼ
ン―シクロヘキサンより再結晶し、表１記載の化
合物（No.11）8.7grを得た。
実施例 ４
Ｎ―〔４―ブロモ―３―（１―カルボキシエチ
ルオキシ）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―ブロモ―３―（１―エトキシカルボ
ニルエチルオキシ）フエニル〕―３，４，５，６
―テトラヒドロフタルイミド1gr、沃化リチウム
5gr、乾燥Ｎ，Ｎジメチルホルムアミド120mlの混
合物を撹拌下に窒素気流中で140℃にて1.5時間加
熱後、室温迄冷却し2N塩酸を加え、エーテルで
抽出した。抽出液を減圧濃縮して得られた結晶を
ベンゼン―シクロヘキサンより再結晶して表１記
載の化合物（No.10）0.72grを得た。
実施例 ５
Ｎ―〔４―ブロモ―３―（１―カルボキシエチ
ルオキシ）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―ブロモ―３―（１―エトキシカルボ
ニルエチルオキシ）フエニル〕―３，４，５，６
―テトラヒドロフタルイミド4.7gr、メタノール
15ml、40％水酸化ナトリウム水溶液４mlの混合物
を撹拌下に１時間加熱還流後、溶媒を減圧下に留
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0.4grおよび氷酢酸20mlを加えて
得られた混合物を撹忰下３時間加熱還流後、１
の水に注ぎ結晶を析出させた。この結晶を取
し、水洗、乾燥後、シリカゲルカラムで酢酸エチ
ル―ｎ―ヘキサン８：１を展開溶媒として溶出
し、表１記載の化合物（No.10）3.8grを得た。
実施例 ６
Ｎ―（４―ブロモ―３―メトキシカルボニルメ
チルオキシ）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―ブロモ―３―カルボキシメチルオキ
シ）フエニル―3.4，５，６―テトラヒドロフタ
ルイミド1.5grおよびメタノール15mlの混合物に、
撹拌下室温にて塩化水素ガスを0.5時間通じた後、
溶媒を留去した後、得られた結晶をシクロヘキサ
ンより再結晶して表１記載の化合物（No.２）
1.5grを得た。
実施例 ７
Ｎ―〔４―ブロモ―３―（１―プロピルメルカ
プトカルボニルプロピルオキシ）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―ブロモ―３―（１―カルボキシプロ
ピルオキシ）フエニル〕―３，４，４，６―テト
ラヒドロフタルイミド2.0grおよび塩化チオニル
2.5mlの混合物を1.5時間加熱還流後、過剰の塩化
チオニルを留去し、残留物をトルエン10mlに溶解
させた。これに１―プロパンチオール0.45grおよ
びトリエチルアミン0.60grのトルエン５ml溶液を
加え、室温にて２時間、その後加熱還流下に0.5
時間撹拌した。
室温迄冷却し、析出せる塩を別し、液を減
圧濃縮した。
得られた油状物をシリカゲルカラムで酢酸エチ
ル―ｎ―ヘキサン１：４を展開溶媒として溶出
し、表１記載の化合物（No.65）2.26grを得た。
実施例 ８
Ｎ―〔４―ブロモ―３―（１―フエナシルオキ
シカルボニルブチルオキシ）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―ブロモ―３―（１―カルボキシブチ
ルオキシ）フエニル〕３，４，５，６―テトラヒ
ドロフタルイミド2.11gr、臭化フエナシル
11.19gr、弗化カリウム0.64grおよびアセトニト
リル10mlの混合物を撹拌下に8.5時間加熱還流後
室温迄冷却し、析出せる塩を別した。液を減
圧濃縮して得られた残留物をシリカゲルカラムで
ベンゼンを展開溶媒として溶出し、表１記載の化
合物（No.141）2.20grを得た。
実施例 ９
Ｎ―〔４―ブロモ―３―（１―メトキシカルボ
ニルエチルオキシ）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―ブロモ―３―（１―エトキシカルボ
ニルエチルオキシ）フエニル〕―３，４，５，６
―テトラヒドロフタルイミド2.5grをメタノール
30mlに溶解せしめ、塩化水素ガスを室温にて0.5
時間通じた後一夜放置した。
析出した結晶を取し、メタノールで洗浄し表
１記載の化合物（No.16）2.21grを得た。
実施例 10
Ｎ―〔４―クロロ―３―（１―エトキシカルボ
ニル―１―プロペニルオキシ）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―クロロ―３―ヒドロキシフエニル）
―３，４，５，６―テトラヒドロフタルイミド
4.0gr、２，３―ジブロモ酪酸エチル4.7gr、炭酸
カリウム2.4grおよびアセトン35mlの混合物を撹
拌下、６時間加熱還流後、析出せる塩を別し
た。液を減圧濃縮し、残留物に2N塩酸を加え
て粗結晶を得た。この粗結晶を水洗、乾燥後、シ
リカゲルカラム（展開溶媒系酢酸エチル―ｎ―ヘ
キサン３：７）で精製し、表１記載の化合物（No.
158）5.2grを得た。
実施例 11
Ｎ―〔４―ブロモ―３―（１―カルボキシブチ
ルオキシ）フエニル〕―３，４，５，６―テト
ラヒドロフタルイミドナトリウム塩の製造
Ｎ―〔４―ブロモ―３―（１―カルボキシブチ
ルオキシ）フエニル〕―３，４，５，６―テトラ
ヒドロフタルイミド2.11grを乾燥ベンゼン20mlに
溶解せしめ、これに水素化ナトリウム0.12grを加
えた。水素の発生が止んだ後、溶媒を留去して表
１記載の化合物（No.84）2.18grを得た。
実施例 12
Ｎ―〔４―クロロ―３―（１―カルボキシペン
チルオキシ）フエニル〕―３，４，５，６―テ
トラヒドロフタルイミドジイソプロピルアミン
塩の製造
Ｎ〔４―クロロ―３―（１―カルボキシペンチ
ルオキシ）フエニル〕―３，４，５，６―テトラ
ヒドロフタルイミド1.18gr、ジイソプロピルアミ
ン0.33grおよびベンゼン８mlの混合物を80℃に５
分間加熱後室温にて一夜放置した。析出する結晶
を取し表１記載の化合物（No.171）1.15gr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する
ことができるが、製造法の詳細は後記表１の製造
法実施例No.で示す。
なお、表１記載の化合物の構造はすべて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] also gives optical isomers. Possible examples of Z-E isomers Compounds of formula (b) included in compounds of formula (I) give ZE isomers. Examples of possible diastereomers; The compound represented by formula (c) included in the compound represented by formula () has two asymmetric centers and gives a diastereomer. The compound represented by the formula () can be produced using various raw materials according to the reaction formula below. In the above reaction formula, Z represents a halogen atom such as chlorine, bromine or iodine. The reaction is carried out in a solvent such as acetone, ethyl methyl ketone, benzene, toluene, acetonitrile, tetrahydrofuran, N,N-dimethylformamide, etc., with a basic compound such as sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, or potassium fluoride. In the presence of fluorine compounds such as cesium fluoride and tetra-n-butylammonium fluoride, and in the presence or absence of iodine compounds such as sodium iodide and potassium iodide.
Performed at ~150°C. The reaction between tetrahydrophthalic anhydride and the above-mentioned anilines is carried out at 60 to 200°C without a solvent or in a solvent such as acetic acid, toluene, methanol, or water. The above hydrolysis reaction consists of (i) water, water-methanol,
Water - in solvents such as ethanol, water, dioxane, etc.
Methanesulfonic acid, p-
It is carried out at 80-180°C in the presence of toluenesulfonic acid. (ii) N,N-dimethylformamide, N-methyl-2-pyrrolidone, 2,4,6-collidine,
In a solvent such as 2,6-lutidine or pyridine, lithium hydroxide, lithium bromide, lithium iodide,
It is carried out at 100-200°C in the presence of sodium iodide, etc. (iii) After reaction at -20 to 150°C in the presence of sodium hydroxide, potassium hydroxide, barium hydroxide, etc. in a solvent such as water, water-methanol, water, -ethanol, water-dioxane, water-acetone, etc. The reaction is carried out by distilling off the solvent and reacting the residue at 50 to 200°C in a solvent such as acetic acid, dilute hydrochloric acid, or dilute hydrochloric acid-dioxane. When producing carboxylic acids represented by the formula () using this reaction, the compounds of the formula () used as raw materials include esters in which B is a methoxy group or an ethoxy group, which are cheaper and easier to obtain. It is preferable to use The above esterification reaction is carried out without solvent using hydrogen chloride,
It is carried out at 0 to 100°C in the presence of an acid catalyst such as sulfuric acid or p-toluenesulfonic acid. In this reaction, a chlorinating agent such as thionyl chloride or phosphorus pentachloride is reacted without a solvent or in a solvent such as benzene, toluene, or xylene at 0 to 150°C to form an acid chloride represented by the formula (). The compound represented by formula () is mixed with a base such as triethylamine, pyridine, N,N-dimethylaniline, sodium bicarbonate, sodium carbonate, potassium carbonate, etc., without a solvent or in a solvent such as benzene, toluene, tetrachloroethane, or trichloroethylene. -20 to 130 in the presence or absence of a sexual compound
It is carried out at ℃. When producing the compound represented by the formula () using this reaction, there is no need to particularly isolate and purify the acid chloride represented by the formula (), and the desired product can be obtained by a one pot reaction. Further, the production of the acid chloride represented by the formula () can be easily confirmed by measuring its IR spectrum. In the above reaction formula, Z represents a halogen atom such as chlorine, bromine or iodine, and B represents a group represented by -OR 3 . This reaction is carried out in a solvent such as acetone, ethyl methyl ketone, benzene, toluene, acetonitrile, tetrahydrofuran, N,N-dimethylformamide, methylene chloride, chloroform, etc., using sodium carbonate, potassium carbonate, metallic sodium, sodium hydride, potassium fluoride. , using an acid binder such as cesium fluoride at 0-150°C. In the above reaction formula, B' represents a specific group among the groups defined above. This transesterification reaction is usually carried out in the absence of a solvent at 0 to 150°C in the presence of an acid catalyst such as hydrogen chloride, sulfuric acid or p-toluenesulfonic acid. In the above reaction formula, Z represents a halogen atom such as chlorine, bromine or iodine. The reaction is carried out in a solvent such as acetone, ethyl methyl ketone, benzene, toluene, acetonitrile, tetrahydrofuran, and N,N-dimethylformamide in the presence of a basic compound such as sodium carbonate, potassium carbonate, sodium hydroxide, or potassium hydroxide. The reaction is carried out at 0 to 150°C in the presence or absence of sodium chloride or potassium iodide. Note that this reaction is thought to proceed through the following intermediate (). In this reaction formula, B represents OR 3 and R 3 represents a salt-forming residue. This salt formation reaction consists of water, water-methanol,
It is carried out at -20°C to 150°C in a solvent such as water-ethanol, benzene, toluene, or tetrahydrofuran. Basic compounds used include alkali metal hydroxides or alkaline earth metals such as sodium hydroxide, potassium hydroxide, and calcium hydroxide, alkali metal hydrides such as sodium hydride and potassium hydride, sodium metal, potassium metal, etc. Examples include alkali metals, ammonia, mono-, di- or trialkylamines, and the like. These compounds can be used as herbicides as they are, but they are usually mixed with an inert liquid carrier or solid carrier, and a suitable surfactant is added thereto to form emulsions, powders, granules, tablets, wettable powders, etc. used as a form of Liquid carriers include toluene, xylene, methylnaphthalene, cyclohexane, butanol, glycol, dimethyl sulfoxide, dimethyl formamide, acetone, methyl isobutyl ketone,
Examples of solid carriers include 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 soybean 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 improvers 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 in the range of 2-80gr per are as the active ingredient. is appropriate. The herbicide of the present invention can be used in either pre-emergence flooded soil treatment or growing season treatment in transplanted paddy 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 stem and leaf combined soil treatment in field crops also 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. The herbicide of the present invention is used, for example, to control the following weeds. Weeds that are dicots, such as wild morning glory,
Chickweed, chickweed, silverwort, pigweed, whiteweed, Japanese crocodile, wild mustard, shepherd's purse, stagweed, knotweed, purslane, dogweed, ragweed, yellowweed, azalea, hawkweed, trumpetweed, horsefly, Japanese chickweed, and Japanese buckwheat. Weeds that are monocotyledonous plants, such as grasshopper, grasshopper, blackberry, foxglove, sycamore, sycamore, cyperus, cyperus, cyperus, cyperus,
Pinus vulgaris, firefly, water cypera, kouki tita, kosanagi, urikawa, yellow-tailed butterfly, and white-tailed butterfly. The herbicide of the present invention can be used as a selective herbicide, for example in the cultivation of the following crops: Dicotyledonous cultivated crops: 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 herbicide of the present invention is not limited to plants of the above-mentioned species and genera, 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 N-[4-bromo-3-(1-ethoxycarbonylbutyloxy)phenyl]-3,4,5,
Production of 6-tetrahydrophthalimide N-(4-bromo-3-hydroxyphenyl)
-3,4,5,6-tetrahydrophthalimide
15.0gr, ethyl alpha-bromovalerate 12.0gr, potassium carbonate 7.7gr, potassium iodide 2.5gr and acetone
After heating 50 ml of the mixture under stirring and refluxing for 3 hours,
It was cooled to room temperature and the salt was separated. The liquid was concentrated under reduced pressure, and 2N hydrochloric acid was added to the residue to precipitate crystals. The crystals were collected, washed with water, dried, and eluted with a silica gel column using ethyl acetate-n-hexane 1:3 as a developing solvent.
I got it. Example 2 N-[4-bromo-3-(1-ethoxycarbonylethyloxy)phenyl]-3,4,5,
Production of 6-tetrahydrophthalimide Cyclohexene-1,2-dicarboxylic anhydride
1.52gr, 4-bromo-3-(1-ethoxycarbonylethyloxy)aniline (n 25 D 1.5590) 2.88gr
A mixture of 10 ml of acetic acid and 10 ml of acetic acid was heated under reflux for 2 hours with stirring, cooled to room temperature, and water was added thereto. After collecting the precipitated crystals, the crystals were recrystallized from benzene-cyclohexane to obtain 3.89 gr of the compound (No. 18) listed in Table 1. Example 3 N-[2,4-dichloro-5-(1-carboxylethyloxy)phenyl]-3,4,5,
Production of 6-tetrahydrophthalimide N-[2,4-dichloro-5-(1-ethoxycarbonylethyloxy)phenyl]-3,4,
A mixture of 14.4 gr of 5,6-tetrahydrophthalimide, 3.40 gr of methanesulfonic acid, and 35 ml of 86% formic acid was heated under reflux for 15 hours with stirring, then cooled to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the obtained oil was tritiated with n-hexane to obtain crystals. This was recrystallized from benzene-cyclohexane to obtain 8.7 gr of the compound (No. 11) listed in Table 1. Example 4 Production of N-[4-bromo-3-(1-carboxyethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide N-[4-bromo-3-(1-ethoxycarbonylethyloxy) ) phenyl]-3,4,5,6
-Tetrahydrophthalimide 1gr, lithium iodide
A mixture of 5gr and 120ml of dry N,N dimethylformamide was heated with stirring at 140°C in a nitrogen stream for 1.5 hours, cooled to room temperature, added with 2N hydrochloric acid, and extracted with ether. The extract was concentrated under reduced pressure, and the resulting crystals were recrystallized from benzene-cyclohexane to obtain 0.72 gr of the compound (No. 10) listed in Table 1. Example 5 Production of N-[4-bromo-3-(1-carboxyethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide N-[4-bromo-3-(1-ethoxycarbonylethyloxy) ) phenyl]-3,4,5,6
-Tetrahydrophthalimide 4.7gr, methanol
A mixture of 15 ml and 4 ml of 40% aqueous sodium hydroxide solution was heated under reflux for 1 hour with stirring, and then the solvent was distilled off under reduced pressure. The mixture obtained by adding 0.4 gr of cyclohexene-1,2-dicarboxylic anhydride and 20 ml of glacial acetic acid to the residue was heated under reflux for 3 hours under stirring, and then
of water to precipitate crystals. The crystals were collected, washed with water, dried, and then eluted with a silica gel column using ethyl acetate-n-hexane 8:1 as a developing solvent to obtain 3.8 gr of the compound (No. 10) listed in Table 1. Example 6 Production of N-(4-bromo-3-methoxycarbonylmethyloxy)phenyl-3,4,5,6-tetrahydrophthalimide N-(4-bromo-3-carboxymethyloxy)phenyl-3.4,5, In a mixture of 1.5 gr of 6-tetrahydrophthalimide and 15 ml of methanol,
After passing hydrogen chloride gas for 0.5 hour at room temperature with stirring,
After distilling off the solvent, the obtained crystals were recrystallized from cyclohexane to obtain the compound (No. 2) listed in Table 1.
Got 1.5gr. Example 7 N-[4-bromo-3-(1-propylmercaptocarbonylpropyloxy)phenyl]-
Production of 3,4,5,6-tetrahydrophthalimide N-[4-bromo-3-(1-carboxypropyloxy)phenyl]-3,4,4,6-tetrahydrophthalimide 2.0gr and thionyl chloride
After heating 2.5 ml of the mixture under reflux for 1.5 hours, excess thionyl chloride was distilled off, and the residue was dissolved in 10 ml of toluene. To this was added 5 ml of toluene solution of 0.45 gr of 1-propanethiol and 0.60 gr of triethylamine, and the mixture was heated at room temperature for 2 hours, then heated to reflux for 0.5 ml of toluene solution.
Stir for hours. The mixture was cooled to room temperature, precipitated salts were separated, and the liquid was concentrated under reduced pressure. The obtained oil was eluted with a silica gel column using ethyl acetate-n-hexane 1:4 as a developing solvent to obtain 2.26 gr of the compound (No. 65) listed in Table 1. Example 8 N-[4-bromo-3-(1-phenacyloxycarbonylbutyloxy)phenyl]-3,
Production of 4,5,6-tetrahydrophthalimide N-[4-bromo-3-(1-carboxybutyloxy)phenyl]3,4,5,6-tetrahydrophthalimide 2.11gr, phenacyl bromide
A mixture of 11.19gr of potassium fluoride, 0.64gr of potassium fluoride, and 10ml of acetonitrile was heated under reflux for 8.5 hours with stirring, then cooled to room temperature, and the precipitated salt was separated. The residue obtained by concentrating the liquid under reduced pressure was eluted with a silica gel column using benzene as a developing solvent to obtain 2.20 gr of the compound (No. 141) listed in Table 1. Example 9 N-[4-bromo-3-(1-methoxycarbonylethyloxy)phenyl]-3,4,5,
Production of 6-tetrahydrophthalimide N-[4-bromo-3-(1-ethoxycarbonylethyloxy)phenyl]-3,4,5,6
- 2.5gr of tetrahydrophthalimide in methanol
Dissolve in 30ml and add 0.5% hydrogen chloride gas at room temperature.
After the time had passed, I left it overnight. The precipitated crystals were collected and washed with methanol to obtain 2.21g of the compound (No. 16) listed in Table 1. Example 10 N-[4-chloro-3-(1-ethoxycarbonyl-1-propenyloxy)phenyl]-
Production of 3,4,5,6-tetrahydrophthalimide N-(4-chloro-3-hydroxyphenyl)
-3,4,5,6-tetrahydrophthalimide
A mixture of 4.0 gr of ethyl 2,3-dibromobutyrate, 4.7 gr of potassium carbonate, 2.4 gr of potassium carbonate, and 35 ml of acetone was heated under reflux for 6 hours with stirring, and the precipitated salt was separated. The liquid was concentrated under reduced pressure, and 2N hydrochloric acid was added to the residue to obtain crude crystals. The crude crystals were washed with water, dried, and then purified with a silica gel column (developing solvent: ethyl acetate-n-hexane 3:7) to produce the compounds listed in Table 1 (No.
158) Got 5.2gr. Example 11 Production of N-[4-bromo-3-(1-carboxybutyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide sodium salt N-[4-bromo-3-(1-carboxybutyl) 2.11 gr of [oxy)phenyl]-3,4,5,6-tetrahydrophthalimide was dissolved in 20 ml of dry benzene, and 0.12 gr of sodium hydride was added thereto. After the generation of hydrogen had stopped, the solvent was distilled off to obtain 2.18 gr of the compound (No. 84) listed in Table 1. Example 12 Production of N-[4-chloro-3-(1-carboxypentyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide diisopropylamine salt N[4-chloro-3-(1-carboxypentyl) A mixture of 1.18 gr of oxy)phenyl-3,4,5,6-tetrahydrophthalimide, 0.33 gr of diisopropylamine and 8 ml of benzene was heated to 80°C for 5 minutes.
After heating for a minute, it was left at room temperature overnight. The precipitated crystals were collected and 1.15g of the compound (No. 171) listed in Table 1 was obtained. Other compounds included in the general formula () can also be produced by any of the methods described above, and the details of the production method are shown in the production method example No. in Table 1 below. The structures of all the compounds listed in Table 1 were confirmed by IR spectra and/or 1 H-NMR spectra.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
製剤例 １ 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。）、白土カーブレツクス＃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
コール硫酸エステル系界面活性剤ソルポール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界性剤エヤロール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ボール
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 13
水田雑草発生前湛水土壤処理試験
2500分の１アールのバツトに水田沖積埴壤土を
充填し、施肥後のタイヌビエ、キカシグサ、ホタ
ルイ、ヘラオモダカの各種子を播種した。この種
子を表層２cm内に良く混合し、深さ約３cmの湛水
状態を維持した。翌日、化合物No.１乃至100、No.
150乃至200を有効成分とする水和剤および比較剤
としてＮ―（３―メトキシ―４―クロルフエニ
ル）―３，４，５，６―テトラヒドロフタルイミ
ド（以下比較剤Ａと略記する。）Ｎ―（３―メト
キシ―４―ブロムフエニル）―３，４，５，６―
テトラヒドロフタルイミド（以下比較剤Ｂと略記
する。）、２，４，６―トリクロルフエニル―4′―
ニトロフエニルエーテル（以下比較剤Ｃと略記す
る。）またはＳ―（２―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Ｄと略記する。）を有効成分とする水和剤を水
で希釈調製し、これを有効成分量として１アール
当り40，20，10，5gとなる様に所定量湛水面に
滴加処理した。
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日目に除草効果の
調査を行つた。
その結果を表２に示す。
尚、評価は
（１−処理区に於ける雑草の地上部生体重／無処理
区に於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), Shirato Curbrex #80
(Shionogi Pharmaceutical Co., Ltd. trademark) 15 parts, N,N kaolin clay (Tsuchiya Kaolin Co., Ltd. trademark), 30 parts and higher alcohol sulfate ester surfactant Solpol 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 Eyarol 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,
In addition, the polyoxyethylene surfactant Solbol
Add 15 parts of 3005X (trademark of Toho Chemical Co., Ltd.) to the active ingredient
An emulsion containing 30% was obtained. Example 13 Flooded soil treatment test before rice field weed emergence A paddy field alluvial clay was filled in a vat of 1/2500 are, and the fertilized seeds of Japanese millet, Kikashigusa, Firefly, and Helaomodaka were sown. These seeds were well mixed within 2 cm of the surface layer to maintain a submerged state at a depth of about 3 cm. The next day, compounds No. 1 to 100, No.
N-(3-methoxy-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide (hereinafter abbreviated as comparative agent A) N-( 3-methoxy-4-bromphenyl)-3,4,5,6-
Tetrahydrophthalimide (hereinafter abbreviated as comparative agent B), 2,4,6-trichlorophenyl-4'-
Nitrophenyl ether (hereinafter abbreviated as comparative agent C) or S-(2-chlorobenzyl)-N,
A wettable powder containing N-diethyl-thiol carbamate (hereinafter abbreviated as Comparative Agent D) as an active ingredient was diluted with water, and the amount of active ingredient was 40, 20, 10, 5g per are. A predetermined amount was added dropwise to the flooded surface. After treatment, the plants were given a reduced water depth of 3 cm/day for 3 days, and then kept in a greenhouse, and the herbicidal effect was investigated on the 21st day after the chemical treatment. The results are shown in Table 2. For evaluation, calculate (1 - above-ground fresh weight of weeds in treated area / above-ground fresh weight of weeds in non-treated area) x 100 = Y (%), and use the herbicidal effect coefficient according to the following criteria. expressed.
【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 14
稚苗水稲に対する薬害試験
5000分の１アールのワグネルポツトに水田沖積
埴壤土を充填し、施肥後適量の水で代掻きを行
い、2.7葉期の水稲苗（品種：ササニシキ、草
丈：14.7cm、苗質：やや良）をポツト当り２本２
株で挿入深約1.5cmの浅植えを行つた。3.5cmの水
深を保ち、移植後翌日または７日目に化合物No.１
乃至50、No.150乃至215を有効成分とする粒剤およ
び比較剤としてＡ，Ｂ，Ｃ，Ｄ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40，20，
10gとす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
温室内で栽培管理し、薬剤処理後21日目に薬害状
況の調査を行つた。
その結果を表３に示す。
尚、評価は
（１−処理区に於ける水稲の地上部生体重／無処理
区に於ける水稲の地上部生体重）×100＝Ｙ（％）
を求め、下記の基準による被害度係数で表わし
た。[Table] Example 14 Phytotoxicity test on young rice seedlings A Wagner pot with a size of 1/5000 are was filled with paddy alluvial clay soil, and after fertilizing, it was raked with an appropriate amount of water. : 14.7cm, seedling quality: Fairly good) 2 plants per pot
Plants were planted shallowly with an insertion depth of approximately 1.5 cm. Maintain a water depth of 3.5 cm and add compound No. 1 on the next day or 7th day after transplanting.
50 to 50, No. 150 to 215 as active ingredients, and granules containing A, B, C, and D as active ingredients as a comparative agent.The active ingredient amount is 40, 20,
A predetermined amount of 10g was dropped onto the flooded surface. After treatment, the plants were given a reduced water depth of 3 cm/day for 3 days, and then cultivated in a greenhouse, and the status of chemical damage was investigated on the 21st day after the chemical treatment. The results are shown in Table 3. For evaluation, calculate (1 - fresh weight of above-ground parts of paddy rice in treated area/live weight of above-ground parts of paddy rice in non-treated area) x 100 = Y (%), and use the damage coefficient according to the following criteria. expressed.
【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 15
畑地土壤処理試験
2500分の１アールの樹脂製バツトに畑地黒ぼく
土壤を充填し、施肥後コムギ、トウモロコシ、ダ
イズ、ワタの各種子を播種して２〜３cmの覆土を
行つた。
この土壤表層内にメヒシバ、タデ、シロザの雑
草種子を播種混合した後、化合物No.25乃至76、No.
105乃至125を有効成分とする水和剤および比較剤
としてＡ，Ｂ，３―（3′，4′―ジクロルフエニ
ル）―１，１―ジメチルウレア（以下比較剤Ｅと
略記する。）または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Ｆと略
記する。）を有効成分とする水和剤を水で希釈調
製し、有効成分量が１アール当り40，20，10gと
なる様に土壤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20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つ
た。
その結果を表４に示す。
尚、除草力の評価は実施例13の基準と同様に表
わし、各作物の薬害についての評価は実施例14の
基準と同様に表わした。[Table] Example 15 Upland Soil Treatment Test A 1/2500 are resin bucket was filled with upland Kuroboku soil, and after fertilization, wheat, corn, soybean, and cotton seeds were sown and covered with 2 to 3 cm of soil. I went. After sowing and mixing weed seeds of crabgrass, knotweed, and whiteweed in the surface layer of this soil, compounds Nos. 25 to 76 and No.
A, B, 3-(3',4'-dichlorophenyl)-1,1-dimethylurea (hereinafter abbreviated as comparative agent E) or 2, as a hydrating agent and comparative agent containing 105 to 125 as active ingredients. 4-dichlorophenyl-
A hydrating agent containing 4'-nitrophenyl ether (hereinafter abbreviated as Comparative Agent F) as an active ingredient was diluted with water, and the amount of active ingredient was 40, 20, and 10 g per 1A on the surface of the clay. It was evenly sprayed using a small powered pressurized sprayer. The herbicidal effect was investigated 20 days after spraying, and at the same time, the chemical damage to each crop was also investigated. The results are shown in Table 4. The evaluation of herbicidal power was expressed in the same manner as in Example 13, and the evaluation of phytotoxicity of each crop was expressed in the same manner as in Example 14.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
実施例 16
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壤を
充填し、施肥後食用ビエ、メヒシバ、ダイコンの
種子を各々ポツト別に播種した。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、メヒ
シバは２葉期、ダイコンは第一本葉期に達した
時、化合物No.１乃至50、No.90乃至120、No.190乃至
205を有効成分とする乳剤および比較剤Ａ，Ｂま
たは３，４―ジクロルプロピオン酸アニリド（以
下比較剤Ｇと略記する。）を有効成分とする乳剤
を水で希釈調製し、有効成分濃度が0.5，0.25，
0.125％となる様にして得られた各調製液を１ア
ール当り10の液量となる様に小型動力加圧噴霧
機で散布処理を行つた。
その後、温室内で観察を続け、薬剤散布後15日
目に除草効果の調査を行つた。
その結果を表５に示す。
尚、評価については実施例13と同様に除草効果
係数で表わした。[Table] Example 16 Stalk and foliage treatment test Small polyethylene pots were filled with upland black soil, and after fertilization, seeds of edible millet, crabgrass, and radish were sown separately in each pot. Cultivation management continued in the greenhouse, and when the test plants reached the two-leaf stage for edible millet, crabgrass and first true leaf stage for radish, compounds No. 1 to 50, No. 90 to 120, No. .190~
An emulsion containing 205 as an active ingredient and an emulsion containing Comparative Agent A, B or 3,4-dichloropropionic acid anilide (hereinafter abbreviated as Comparative Agent G) as an active ingredient were diluted with water to determine the concentration of the active ingredient. 0.5，0.25，
Each of the prepared liquids obtained at a concentration of 0.125% was sprayed using a small power pressurized sprayer at a volume of 10 liquid per are. Afterwards, observations were continued in the greenhouse, and the herbicidal effect was investigated 15 days after spraying. The results are shown in Table 5. Note that the evaluation was expressed in terms of herbicidal effect coefficients as in Example 13.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
Claims (1)
を示し；Ａは【式】（式中、R1は水素原 子、アルキル基、または、ハロゲン原子で置換さ
れていてもよいフエニル基を示し、R2は水素原
子または低級アルキル基を示し、ｎは１〜３の整
数を示す）、【式】または、―CH2CH＝ CH―を示し、；Ｂは―OR3（式中、R3は水素原
子、アルキル基、アルケニル基、炭素数３〜４の
アルキニル基、ハロアルキル基、ハロアルケニル
基、シアノアルキル基、ヒドロキシアルキル基、
アルコキシアルキル基、アルコキシアルコキシア
ルキル基、アルコキシアルコキシアルコキシアル
キル基、アルキルチオアルキル基、シクロアルキ
ル基、アラルキル基、フエニル基、または、メチ
ル基で置換されていてもよいγ―ブチロラクトン
基を示す）、―SR4（式中、R4はアルキル基、アル
コキシカルボニルアルキル基またはベンジル基を
示す）、【式】（式中、R5は水 素原子またはメチル基を示し、R6はメチル基ま
たはフエニル基を示し、ｍは１から３の整数を示
す）、または、アルカリ金属、アルカリ土金属、
および、アルキル基で置換されていてもよいアン
モニウム基から選ばれる塩形成残基を示す。〕 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、Ｘ，Ｙは水素原子またはハロゲン原子
を示し；Ａは【式】（式中、R1は水素原 子、アルキル基、または、ハロゲン原子で置換さ
れていてもよいフエニル基を示し、R2は水素原
子または低級アルキル基を示し、ｎは１〜３の整
数を示す）、【式】または、―CH2CH＝ CH―を示し、；Ｂは―OR3（式中、R3は水素原
子、アルキル基、アルケニル基、炭素数３〜４の
アルキニル基、ハロアルキル基、ハロアルケニル
基、シアノアルキル基、ヒドロキシアルキル基、
アルコキシアルキル基、アルコキシアルコキシア
ルキル基、アルコキシアルコキシアルコキシアル
キル基、アルキルチオアルキル基、シクロアルキ
ル基、アラルキル基、フエニル基、または、メチ
ル基で置換されていてもよいγ―ブチロラクトン
基を示す）、―SR4（式中、R4はアルキル基、アル
コキシカルボニルアルキル基またはベンジル基を
示す）、【式】（式中、R5は水 素原子またはメチル基を示し、R6はメチル基ま
たはフエニル基を示し、ｍは１から３の整数を示
す）、または、アルカリ金属、アルカリ土金属、
および、アルキル基で置換されていてもよいアン
モニウム基から選ばれる塩形成残基を示す。〕 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, X and Y represent a hydrogen atom or a halogen atom; R 2 represents a hydrogen atom or a lower alkyl group, n represents an integer of 1 to 3), [Formula] or -CH 2 CH= CH-; B represents -OR 3 (In the formula, R is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group having 3 to 4 carbon atoms, a haloalkyl group, a haloalkenyl group, a cyanoalkyl group, a hydroxyalkyl group,
(represents an alkoxyalkyl group, an alkoxyalkoxyalkyl group, an alkoxyalkoxyalkoxyalkyl group, an alkylthioalkyl group, a cycloalkyl group, an aralkyl group, a phenyl group, or a γ-butyrolactone group optionally substituted with a methyl group), -SR 4 (in the formula, R 4 represents an alkyl group, an alkoxycarbonylalkyl group or a benzyl group), [Formula] (in the formula, R 5 represents a hydrogen atom or a methyl group, and R 6 represents a methyl group or a phenyl group) , m represents an integer from 1 to 3), or an alkali metal, an alkaline earth metal,
and a salt-forming residue selected from an ammonium group optionally substituted with an alkyl group. ] Tetrahydrophthalimides represented by. 2 General formula [In the formula, X and Y represent a hydrogen atom or a halogen atom; R 2 represents a hydrogen atom or a lower alkyl group, n represents an integer of 1 to 3), [Formula] or -CH 2 CH= CH-; B represents -OR 3 (In the formula, R is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group having 3 to 4 carbon atoms, a haloalkyl group, a haloalkenyl group, a cyanoalkyl group, a hydroxyalkyl group,
(represents an alkoxyalkyl group, an alkoxyalkoxyalkyl group, an alkoxyalkoxyalkoxyalkyl group, an alkylthioalkyl group, a cycloalkyl group, an aralkyl group, a phenyl group, or a γ-butyrolactone group optionally substituted with a methyl group), -SR 4 (in the formula, R 4 represents an alkyl group, an alkoxycarbonylalkyl group or a benzyl group), [Formula] (in the formula, R 5 represents a hydrogen atom or a methyl group, and R 6 represents a methyl group or a phenyl group) , m represents an integer from 1 to 3), or an alkali metal, an alkaline earth metal,
and a salt-forming residue selected from an ammonium group optionally substituted with an alkyl group. ] A herbicide containing a tetrahydrophthalimide represented by the following as an active ingredient.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14007680A JPH0245621B2 (en) | 1980-10-07 | 1980-10-07 | TETORAHIDOROFUTARUIMIDORUIOYOBIKOREOJUKOSEIBUNTOSURUJOSOZAI |
| US06/308,825 US4536209A (en) | 1980-10-07 | 1981-10-05 | N-(3-substituted oxyphenyl)tetrahydrophthalimides and herbicidal composition |
| EP81107937A EP0049508A1 (en) | 1980-10-07 | 1981-10-05 | N-(3-Substituted oxyphenyl) tetrahydrophthalimides and herbicidal composition |
| CA000387319A CA1163635A (en) | 1980-10-07 | 1981-10-05 | N-(3-substituted oxyphenyl)-tetrahydrophthalimides and herbicidal composition |
| BR8106478A BR8106478A (en) | 1980-10-07 | 1981-10-07 | COMPOUNDS HERBICIDE COMPOSITION PROCESS FOR WEED CONTROL IN A CULTURE AND PROCESS FOR THE PRODUCTION OF SUCH COMPOUNDS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14007680A JPH0245621B2 (en) | 1980-10-07 | 1980-10-07 | TETORAHIDOROFUTARUIMIDORUIOYOBIKOREOJUKOSEIBUNTOSURUJOSOZAI |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5764671A JPS5764671A (en) | 1982-04-19 |
| JPH0245621B2 true JPH0245621B2 (en) | 1990-10-11 |
Family
ID=15260398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14007680A Expired - Lifetime JPH0245621B2 (en) | 1980-10-07 | 1980-10-07 | TETORAHIDOROFUTARUIMIDORUIOYOBIKOREOJUKOSEIBUNTOSURUJOSOZAI |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0245621B2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58131969A (en) * | 1982-01-29 | 1983-08-06 | Sumitomo Chem Co Ltd | 2-phenyl-4,5,6,7-tetrahydro-2h-isoindole derivative, its preparation and herbicide containing said derivative as active component |
| JPS58135864A (en) * | 1982-02-05 | 1983-08-12 | Sumitomo Chem Co Ltd | 2-phenyl-4,5,6,7-tetrahydro-2h-indole derivative, its preparation and herbicide comprising it as active ingredient |
| JPS58110566A (en) * | 1981-12-25 | 1983-07-01 | Sumitomo Chem Co Ltd | 2-phenyl-4,5,6,7-tetrahydro-2h-isoindole derivative, its preparation and herbicide containing said derivative as active component |
| JPS58192868A (en) * | 1982-05-06 | 1983-11-10 | Sumitomo Chem Co Ltd | 2-phenyl-4,5,6,7-tetrahydro-2h-isoindole derivative, its preparation and herbicide containing said compound as active component |
| JPS5953466A (en) * | 1982-09-21 | 1984-03-28 | Sumitomo Chem Co Ltd | N-phenyltetrahydrophthalimide derivative, its preparation and herbicide containing said derivative as active component |
| JPS5965074A (en) * | 1982-10-06 | 1984-04-13 | Sumitomo Chem Co Ltd | 2-phenyl-4,5,6,7-tetrahydro-2h-isoindole derivative, its preparation and herbicide containing it as active ingredient |
| 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 |
-
1980
- 1980-10-07 JP JP14007680A patent/JPH0245621B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5764671A (en) | 1982-04-19 |
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