JPS6320427B2 - - Google Patents
Info
- Publication number
- JPS6320427B2 JPS6320427B2 JP14177680A JP14177680A JPS6320427B2 JP S6320427 B2 JPS6320427 B2 JP S6320427B2 JP 14177680 A JP14177680 A JP 14177680A JP 14177680 A JP14177680 A JP 14177680A JP S6320427 B2 JPS6320427 B2 JP S6320427B2
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydrophthalimide
- phenyl
- atom
- parts
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 230000002363 herbicidal effect Effects 0.000 description 23
- 239000004480 active ingredient Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 17
- -1 N-(2,4-dichloro-5-cyanomethoxyphenyl)-3,4,5,6-tetrahydrophthalimide Chemical compound 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000004009 herbicide Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002689 soil Substances 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241000234653 Cyperus Species 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- SPAMRUYRVYMHPV-UHFFFAOYSA-N 3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical class C1=CCCC2C(=O)NC(=O)C21 SPAMRUYRVYMHPV-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- AFJWMGOTLUUGHF-UHFFFAOYSA-N 4,5,6,7-tetrahydroisoindole-1,3-dione Chemical class C1CCCC2=C1C(=O)NC2=O AFJWMGOTLUUGHF-UHFFFAOYSA-N 0.000 description 2
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- 235000004405 Ageratum conyzoides Nutrition 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 240000000486 Lepidium draba Species 0.000 description 2
- 235000000391 Lepidium draba Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 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
- 244000088415 Raphanus sativus Species 0.000 description 2
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- 235000012211 aluminium silicate Nutrition 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
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 230000000887 hydrating effect Effects 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
- 239000007788 liquid Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring 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
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 239000008096 xylene Substances 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
- ZTWKFBCCQIPEKB-UHFFFAOYSA-N 2-(4-bromo-3-hydroxyphenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Br)C(O)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 ZTWKFBCCQIPEKB-UHFFFAOYSA-N 0.000 description 1
- 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
- WDWZKDSIKMGTOR-UHFFFAOYSA-N 2-(5-amino-2-chlorophenoxy)acetonitrile Chemical compound NC1=CC=C(Cl)C(OCC#N)=C1 WDWZKDSIKMGTOR-UHFFFAOYSA-N 0.000 description 1
- CNHZUQAHWWNRBK-UHFFFAOYSA-N 2-[2-bromo-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)phenoxy]acetonitrile Chemical compound C1=C(OCC#N)C(Br)=CC=C1N1C(=O)C(CCCC2)=C2C1=O CNHZUQAHWWNRBK-UHFFFAOYSA-N 0.000 description 1
- MJUJEQMBJPNYKZ-UHFFFAOYSA-N 2-[2-bromo-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)phenoxy]hexanenitrile Chemical compound C1=C(Br)C(OC(CCCC)C#N)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 MJUJEQMBJPNYKZ-UHFFFAOYSA-N 0.000 description 1
- GGZVBJFVHGTFTP-UHFFFAOYSA-N 2-[2-bromo-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)phenoxy]propanenitrile Chemical compound C1=C(Br)C(OC(C)C#N)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 GGZVBJFVHGTFTP-UHFFFAOYSA-N 0.000 description 1
- RLEGPPMNFHTOFA-UHFFFAOYSA-N 2-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)phenoxy]acetonitrile Chemical compound C1=C(OCC#N)C(Cl)=CC=C1N1C(=O)C(CCCC2)=C2C1=O RLEGPPMNFHTOFA-UHFFFAOYSA-N 0.000 description 1
- HYVNNNVJZXLHNG-UHFFFAOYSA-N 2-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)phenoxy]butanenitrile Chemical compound C1=C(Cl)C(OC(CC)C#N)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 HYVNNNVJZXLHNG-UHFFFAOYSA-N 0.000 description 1
- SGQZILOPSFANSR-UHFFFAOYSA-N 2-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)phenoxy]hexanenitrile Chemical compound C1=C(Cl)C(OC(CCCC)C#N)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 SGQZILOPSFANSR-UHFFFAOYSA-N 0.000 description 1
- QYDZSFQJEPDMGH-UHFFFAOYSA-N 2-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)phenoxy]propanenitrile Chemical compound C1=C(Cl)C(OC(C)C#N)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 QYDZSFQJEPDMGH-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 239000002994 raw material Substances 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000002364 soil amendment Substances 0.000 description 1
- 239000002881 soil fertilizer Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
Landscapes
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14177680A JPS5767560A (en) | 1980-10-09 | 1980-10-09 | Tetrahydrophthalimide and herbicide containing the same |
| 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 |
| US06/308,825 US4536209A (en) | 1980-10-07 | 1981-10-05 | N-(3-substituted oxyphenyl)tetrahydrophthalimides and herbicidal composition |
| BR8106478A BR8106478A (pt) | 1980-10-07 | 1981-10-07 | Compostos composicao herbicida processo para controle de ervas daninhas em uma cultura e processo para producao de tais compostos |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14177680A JPS5767560A (en) | 1980-10-09 | 1980-10-09 | Tetrahydrophthalimide and herbicide containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5767560A JPS5767560A (en) | 1982-04-24 |
| JPS6320427B2 true JPS6320427B2 (enrdf_load_stackoverflow) | 1988-04-27 |
Family
ID=15299898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14177680A Granted JPS5767560A (en) | 1980-10-07 | 1980-10-09 | Tetrahydrophthalimide and herbicide containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5767560A (enrdf_load_stackoverflow) |
-
1980
- 1980-10-09 JP JP14177680A patent/JPS5767560A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5767560A (en) | 1982-04-24 |
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