JPH0143732B2 - - Google Patents
Info
- Publication number
- JPH0143732B2 JPH0143732B2 JP56166343A JP16634381A JPH0143732B2 JP H0143732 B2 JPH0143732 B2 JP H0143732B2 JP 56166343 A JP56166343 A JP 56166343A JP 16634381 A JP16634381 A JP 16634381A JP H0143732 B2 JPH0143732 B2 JP H0143732B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl group
- lower alkyl
- group
- benzene
- hydrogen atom
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 230000002363 herbicidal effect Effects 0.000 claims description 14
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 10
- 239000004009 herbicide Substances 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 230000006378 damage Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- -1 dimethylphenoxy Chemical group 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 229930192334 Auxin Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 244000301850 Cupressus sempervirens Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000002363 auxin 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
- 239000000969 carrier Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 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
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HIJGEOLLVWCERD-UHFFFAOYSA-N n-benzyl-2-(3,5-dimethylphenoxy)butanamide Chemical compound C=1C=CC=CC=1CNC(=O)C(CC)OC1=CC(C)=CC(C)=C1 HIJGEOLLVWCERD-UHFFFAOYSA-N 0.000 description 2
- VCMUDUGCNXORRR-UHFFFAOYSA-N n-benzyl-2-(4-chloro-3-methylphenoxy)pentanamide Chemical compound C=1C=CC=CC=1CNC(=O)C(CCC)OC1=CC=C(Cl)C(C)=C1 VCMUDUGCNXORRR-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000013459 phenoxy herbicide Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 1
- UFWSTLURZCKNHB-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)butanoyl chloride Chemical compound CCC(C(Cl)=O)OC1=CC(Cl)=CC(Cl)=C1 UFWSTLURZCKNHB-UHFFFAOYSA-N 0.000 description 1
- YQCBRBMIKOTNPC-UHFFFAOYSA-N 2-(3,5-dimethylphenoxy)butanoyl chloride Chemical compound CCC(C(Cl)=O)OC1=CC(C)=CC(C)=C1 YQCBRBMIKOTNPC-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001520921 Leersia virginica Species 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- HTJOSNUJPXUNGU-UHFFFAOYSA-N n-benzyl-2-bromopentanamide Chemical compound CCCC(Br)C(=O)NCC1=CC=CC=C1 HTJOSNUJPXUNGU-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Inorganic materials [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16634381A JPS5867653A (ja) | 1981-10-20 | 1981-10-20 | フエノキシアルカン酸のベンジルアミド誘導体および除草剤 |
GB08228676A GB2108498B (en) | 1981-10-20 | 1982-10-07 | Phenoxyalkylamide derivative, process for preparing the same, herbicidal composition containing the same and method for controlling weeds by the use of the same |
DE3237998A DE3237998C2 (de) | 1981-10-20 | 1982-10-13 | Phenoxyalkylamidderivate, Verfahren zu deren Herstellung und herbizide Zusammensetzungen, welche diese enthalten |
CA000413389A CA1188697A (en) | 1981-10-20 | 1982-10-14 | Phenoxyalkylamide derivative, process for preparing the same, herbicidal composition containing the same and method for controlling weeds by the use of the same |
FR8217318A FR2514757B1 (fr) | 1981-10-20 | 1982-10-15 | Phenoxyalkylamides, leur preparation, compositions herbicides en contenant et leur utilisation dans la destruction des mauvaises herbes |
KR8204683A KR880002603B1 (ko) | 1981-10-20 | 1982-10-18 | 페녹시알킬아마이드 유도체의 제조방법 |
BR8206093A BR8206093A (pt) | 1981-10-20 | 1982-10-19 | Derivado de fenoxialquilamida,processo para sua preparacao,composicao herbicida contendo tal derivado e processo para controle de ervas daninhas pelo uso do mesmo |
US06/579,655 US4753674A (en) | 1981-10-20 | 1984-02-13 | Herbicidal composition containing a phenoxyalkylamide derivative and method for controlling weeds by the use of the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16634381A JPS5867653A (ja) | 1981-10-20 | 1981-10-20 | フエノキシアルカン酸のベンジルアミド誘導体および除草剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5867653A JPS5867653A (ja) | 1983-04-22 |
JPH0143732B2 true JPH0143732B2 (ru) | 1989-09-22 |
Family
ID=15829607
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16634381A Granted JPS5867653A (ja) | 1981-10-20 | 1981-10-20 | フエノキシアルカン酸のベンジルアミド誘導体および除草剤 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5867653A (ru) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58113156A (ja) * | 1981-12-28 | 1983-07-05 | Ube Ind Ltd | フエノキシアルカン酸のベンジルアミド誘導体および除草剤 |
EP2731608B1 (en) * | 2011-07-13 | 2018-03-14 | Microbiotix, Inc. | Inhibitors of bacterial type iii secretion system |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52120123A (en) * | 1976-04-02 | 1977-10-08 | Ube Ind Ltd | Herbicide |
JPS5396323A (en) * | 1977-02-02 | 1978-08-23 | Hodogaya Chem Co Ltd | Herbicide |
JPS5657752A (en) * | 1979-10-15 | 1981-05-20 | Sumitomo Chem Co Ltd | M-diaminobenzene derivative, its preparation, and herbicide constaining said compound as effective component |
-
1981
- 1981-10-20 JP JP16634381A patent/JPS5867653A/ja active Granted
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52120123A (en) * | 1976-04-02 | 1977-10-08 | Ube Ind Ltd | Herbicide |
JPS5396323A (en) * | 1977-02-02 | 1978-08-23 | Hodogaya Chem Co Ltd | Herbicide |
JPS5657752A (en) * | 1979-10-15 | 1981-05-20 | Sumitomo Chem Co Ltd | M-diaminobenzene derivative, its preparation, and herbicide constaining said compound as effective component |
Also Published As
Publication number | Publication date |
---|---|
JPS5867653A (ja) | 1983-04-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH0143732B2 (ru) | ||
KR880002603B1 (ko) | 페녹시알킬아마이드 유도체의 제조방법 | |
JP2810544B2 (ja) | N−アシル−n−フェニルテトラヒドロフタラミン酸誘導体、その製造法およびそれを有効成分とする除草剤 | |
JPS6127962A (ja) | N−置換ジカルボキシミド類およびこれを有効成分とする除草剤 | |
JPH0142257B2 (ru) | ||
JPS585900B2 (ja) | 新規ジフェニルエ−テル系化合物と殺草剤 | |
JPH0655705B2 (ja) | アシルアミノバレロニトリル誘導体、その製造法およびそれらを含有する除草剤および農園芸用殺菌剤 | |
JPS6054954B2 (ja) | ジフエニルエ−テル誘導体,およびジフエニルエ−テル誘導体を含有する除草剤 | |
JPS5827763B2 (ja) | 除草剤 | |
JP2650824B2 (ja) | N−アシル−n−フェニルマレアミド酸誘導体およびその製造法ならびにそれを有効成分とする除草剤 | |
JPS6365063B2 (ru) | ||
JPS5976045A (ja) | α,α−ジメチルフエニル酢酸アニリド誘導体、その製造法及びそれを含有する除草剤 | |
JPH0259141B2 (ru) | ||
JPS5911561B2 (ja) | 農園芸用土壌殺菌剤 | |
JP2745737B2 (ja) | ベンジリデンアミノオキシアルカン酸アミド誘導体、その製造法及び除草剤 | |
JPH0142256B2 (ru) | ||
JPH02115157A (ja) | スルホニルグリシン誘導体および除草剤 | |
KR830001714B1 (ko) | 디페닐 에테르 유도체의 제조방법 | |
JPS6353184B2 (ru) | ||
JPS585163B2 (ja) | サツソウザイ | |
JPH05230034A (ja) | ピリミジン誘導体、その製造法およびそれを有効成分とする除草剤 | |
JPS59130847A (ja) | α−メチル−α−エチルフェニル酢酸アニリド誘導体、その製造法及びそれを含有する除草剤 | |
JPS6145985B2 (ru) | ||
JPS61126003A (ja) | 除草剤 | |
JPS61134373A (ja) | テトラヒドロフタルイミド誘導体、その製造法およびそれを有効成分とする除草剤 |