JPH0247464B2 - - Google Patents
Info
- Publication number
- JPH0247464B2 JPH0247464B2 JP56138044A JP13804481A JPH0247464B2 JP H0247464 B2 JPH0247464 B2 JP H0247464B2 JP 56138044 A JP56138044 A JP 56138044A JP 13804481 A JP13804481 A JP 13804481A JP H0247464 B2 JPH0247464 B2 JP H0247464B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- compound
- group
- chloro
- weight
- 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
- 230000002363 herbicidal effect Effects 0.000 claims description 19
- 239000004009 herbicide Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 240000008042 Zea mays Species 0.000 claims description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 9
- 235000005822 corn Nutrition 0.000 claims description 9
- CCFNMXDJVOYPEY-UHFFFAOYSA-N 2-phenyl-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical class O=C1C2CCC=CC2C(=O)N1C1=CC=CC=C1 CCFNMXDJVOYPEY-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 31
- 241000196324 Embryophyta Species 0.000 description 27
- -1 etc.) Polymers 0.000 description 19
- 239000002689 soil Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 244000025254 Cannabis sativa Species 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- 240000001549 Ipomoea eriocarpa Species 0.000 description 3
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 3
- 244000062793 Sorghum vulgare Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- CGWJDVCUCCBSNL-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Cl)C(O)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F CGWJDVCUCCBSNL-UHFFFAOYSA-N 0.000 description 2
- QAWLSTWQUFLACC-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-prop-2-ynoxyphenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound FC1=CC(Cl)=C(OCC#C)C=C1N1C(=O)C(CCCC2)=C2C1=O QAWLSTWQUFLACC-UHFFFAOYSA-N 0.000 description 2
- MFUPLJQNEXUUDW-UHFFFAOYSA-N 2-phenylisoindole-1,3-dione Chemical class O=C1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 MFUPLJQNEXUUDW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 240000008955 Dioscorea japonica Species 0.000 description 2
- 235000005251 Dioscorea japonica Nutrition 0.000 description 2
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000254158 Lampyridae Species 0.000 description 2
- 229920001732 Lignosulfonate Polymers 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 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
- 239000004202 carbamide Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 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
- 239000004563 wettable powder Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FLTFAXYVWNGCHY-UHFFFAOYSA-N 1-[(6,6-dimethylcyclohexa-2,4-dien-1-yl)methyl]-3-(4-methylphenyl)urea Chemical compound C1=CC(C)=CC=C1NC(=O)NCC1C(C)(C)C=CC=C1 FLTFAXYVWNGCHY-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- XVIRIXVOLLJIPF-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1[N+]([O-])=O XVIRIXVOLLJIPF-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 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
- IGYXYGDEYHNFFT-UHFFFAOYSA-N 2-chloro-4-fluorophenol Chemical compound OC1=CC=C(F)C=C1Cl IGYXYGDEYHNFFT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- ITUJTNVTYSHLGM-UHFFFAOYSA-N 2-methylsulfanyl-4,6-di(propan-2-yl)-2h-1,3,5-triazin-1-amine Chemical compound CSC1N=C(C(C)C)N=C(C(C)C)N1N ITUJTNVTYSHLGM-UHFFFAOYSA-N 0.000 description 1
- TVHCLUNXRJSPGX-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1,1-dimethylurea;3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1.CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 TVHCLUNXRJSPGX-UHFFFAOYSA-N 0.000 description 1
- VLSWUCCBDZJTNF-UHFFFAOYSA-N 3-(aminomethylsulfanyl)-6-tert-butyl-4H-1,2,4-triazin-5-one Chemical compound NCSC1=NN=C(C(N1)=O)C(C)(C)C VLSWUCCBDZJTNF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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
- UDVZOMAEGATTSE-UHFFFAOYSA-N 4-methyl-2,6-dinitro-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O UDVZOMAEGATTSE-UHFFFAOYSA-N 0.000 description 1
- AFZLCOLNTRPSIF-UHFFFAOYSA-N 5-amino-2-chloro-4-fluorophenol Chemical compound NC1=CC(O)=C(Cl)C=C1F AFZLCOLNTRPSIF-UHFFFAOYSA-N 0.000 description 1
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000480037 Argyrosomus japonicus Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000209763 Avena sativa Species 0.000 description 1
- 235000007558 Avena sp Nutrition 0.000 description 1
- 240000008100 Brassica rapa Species 0.000 description 1
- 235000011292 Brassica rapa Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 244000277285 Cassia obtusifolia Species 0.000 description 1
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920002871 Dammar gum Polymers 0.000 description 1
- 239000004860 Dammar gum Substances 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- YWBVHLJPRPCRSD-UHFFFAOYSA-N Fluridone Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC=C1 YWBVHLJPRPCRSD-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- LRUUNMYPIBZBQH-UHFFFAOYSA-N Methazole Chemical compound O=C1N(C)C(=O)ON1C1=CC=C(Cl)C(Cl)=C1 LRUUNMYPIBZBQH-UHFFFAOYSA-N 0.000 description 1
- 240000003433 Miscanthus floridulus Species 0.000 description 1
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 description 1
- 241000681978 Rhododendron japonicum Species 0.000 description 1
- WOZQBERUBLYCEG-UHFFFAOYSA-N SWEP Chemical compound COC(=O)NC1=CC=C(Cl)C(Cl)=C1 WOZQBERUBLYCEG-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UHJMECPUUCQFRL-UHFFFAOYSA-N ethyl 2-(2,6-diethylanilino)acetate Chemical compound CCOC(=O)CNC1=C(CC)C=CC=C1CC UHJMECPUUCQFRL-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- OXHDYFKENBXUEM-UHFFFAOYSA-N glyphosine Chemical compound OC(=O)CN(CP(O)(O)=O)CP(O)(O)=O OXHDYFKENBXUEM-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000004898 kneading Methods 0.000 description 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000013459 phenoxy herbicide Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、
(1) 一般式()
〔式中、Rは炭素数1〜4のアルキル基、炭素
数3〜4のアルケニル基または炭素数3〜4の
アルキニル基を表わす。ただし、Rがイソプロ
ピル基である場合は含まれない。〕
で示されるN−フエニルテトラヒドロフタルイ
ミド誘導体、
(2) 一般式()
RX ()
〔式中、Rは前述のとおりであり、Xはハロゲ
ン原子を表わす。〕
で示されるハロゲン化合物とN−(4−クロロ
−2−フルオロ−5−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と
を塩基の存在下で反応させることを特徴とする
一般式()で示されるN−フエニルフタルイ
ミド誘導体の製造法および(3)一般式()で示
される化合物を有効成分として含有する除草剤
である。
従来N−フエニルテトラヒドロフタルイミド誘
導体が除草活性を有することは特公昭48−11940
号公報等において公知である。本発明者らは、テ
トラヒドロフタルイミド誘導体に関して研究を進
めてきた結果、N−(4−クロロ−2−フルオロ
−5−イソプロポキシフエニル)−3,4,5,
6−テトラヒドロフタルイミドがきわめて低薬量
で優れた除草効力を有し、同時にトウモロコシ等
の重要作物に選択性を有することを見い出した
(特開昭57−163365号)が、引きつづき同系統化
合物の研究を続けてきた結果、一般式()で示
される化合物群が同様に低薬量で優れた除草効力
を有し、かつトウモロコシ、ワタ、ダイズ、イネ
などの重要作物に対して、雑草に対して除草活性
を示す薬量ではほとんど影響を与えないという優
れた性質を見出すにいたり、本発明を完成した。
さらに詳しくは、本発明化合物を細状土壌処理、
茎葉処理において用いた場合、既存の類似化合
物、たとえば特開昭51−51521号および特開昭55
−139305号公報等に記載の化合物に比較して、格
段に優れた除草作用を有し、ワタ、ダイズ、トウ
モロコシ等の重要作物に選択性を有し、また水田
において用いた場合、イネに対して害が少なく既
存の類似化合物に比べてより強い除草作用を示
し、該化合物では活性の見出されていないタイヌ
ビエ、ホタルイ、ウリカワに対しても優れた除草
作用を有している。本発明化合物は細状土壌処
理、茎葉処理で用いた場合にトウモロコシに対し
て安全に使用できることが特に優れた性質といえ
る。
次に本発明化合物の製造法について詳しく説明
する。一般式()で示される化合物は下記の反
応式に従つて合成され得る。
〔式中、RおよびXは前述のとおりである。〕
この反応はジメチルホルムアミド、ジメチルス
ルホキサイド等の極性非プロトン溶媒中、炭酸カ
リウム、炭酸ナトリウム等の塩基を用いて室温、
必要な場合は加熱することで行なわれる。原料化
合物であるN−(4−クロロ−2−フルオロ−5
−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は、既知化合物である2−
クロロ−4−フルオロフエノールより合成された
5−アミノ−2−クロロ−4−フルオロフエノー
ルと3,4,5,6−テトラヒドロフタル酸無水
物との反応で得られる(特願昭56−47816号)。
次に実施例をあげ本発明をより詳しく説明す
る。
実施例 1
N−(4−クロロ−2−フルオロ−5−プロパ
ルギルオキシフエニル)−3,4,5,6−テト
ラヒドロフタルイミド(化合物8)N−(4−ク
ロロ−2−フルオロ−5−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1
gをジメチルホルムアミド10mlに溶解し、室温で
無水炭酸カリウム0.34gを加え撹拌した。40℃付
近で30分間撹拌した後、臭化プロパルギル1gを
加え50〜60℃で3時間撹拌した。室温まで放冷
後、反応液を水にあけ、エーテル抽出した。エー
テル層は水洗して無水硫酸ナトリウムで乾燥、濃
縮残渣をシリカゲルカラムクロマトグラフイーに
より精製し、0.8gの結晶を得た。mp136.4℃
元素分析値
実測値 C(%) 61.09 H(%) 4.00
N(%) 4.20
計算値 C(%) 61.18 H(%) 4.19
N(%) 3.92
実施例1と同様の方法で第1表に示した化合物
を合成した。
The present invention has the following features: (1) General formula () [In the formula, R represents an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, or an alkynyl group having 3 to 4 carbon atoms. However, it is not included when R is an isopropyl group. ] N-phenyltetrahydrophthalimide derivative represented by (2) general formula () RX () [wherein R is as described above and X represents a halogen atom. ] A halogen compound represented by and N-(4-chloro-2-fluoro-5-hydroxyphenyl)-
A method for producing an N-phenylphthalimide derivative represented by the general formula (), characterized by reacting 3,4,5,6-tetrahydrophthalimide in the presence of a base, and (3) a method for producing an N-phenylphthalimide derivative represented by the general formula (). It is a herbicide containing a compound as an active ingredient. Conventionally, it was reported in Japanese Patent Publication No. 11940-1973 that N-phenyltetrahydrophthalimide derivatives have herbicidal activity.
It is publicly known in the publication No. The present inventors have conducted research on tetrahydrophthalimide derivatives and found that N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-3,4,5,
It was discovered that 6-tetrahydrophthalimide has excellent herbicidal efficacy at an extremely low dose and at the same time has selectivity for important crops such as corn (Japanese Patent Application Laid-open No. 163365/1983). As a result of continued research, we have found that the compound group represented by the general formula () has similarly excellent herbicidal efficacy at low doses and is effective against weeds in important crops such as corn, cotton, soybean, and rice. The present invention has been completed based on the discovery of the excellent property that the herbicidal activity has almost no effect at the dosage level.
More specifically, the compound of the present invention is applied to fine soil treatment,
When used in foliage treatment, existing similar compounds, such as JP-A-51-51521 and JP-A-55
-Compared to the compounds described in Publication No. 139305, etc., it has significantly superior herbicidal activity and is selective for important crops such as cotton, soybean, and corn, and when used in rice fields, it is effective against rice. It is less harmful and has a stronger herbicidal effect than existing similar compounds, and also has excellent herbicidal activity against Japanese millet, firefly, and silver grass, for which no activity has been found with these compounds. It can be said that the compound of the present invention has a particularly excellent property that it can be safely used on corn when used in fine soil treatment and foliage treatment. Next, the method for producing the compound of the present invention will be explained in detail. The compound represented by the general formula () can be synthesized according to the reaction formula below. [In the formula, R and X are as described above.] ] This reaction is carried out at room temperature using a base such as potassium carbonate or sodium carbonate in a polar aprotic solvent such as dimethylformamide or dimethyl sulfoxide.
This is done by heating if necessary. The raw material compound N-(4-chloro-2-fluoro-5
-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide is a known compound 2-
Obtained by the reaction of 5-amino-2-chloro-4-fluorophenol synthesized from chloro-4-fluorophenol and 3,4,5,6-tetrahydrophthalic anhydride (Japanese Patent Application No. 56-47816) ). Next, the present invention will be explained in more detail with reference to Examples. Example 1 N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-3,4,5,6-tetrahydrophthalimide (compound 8) N-(4-chloro-2-fluoro-5-hydroxy phenyl)
-3,4,5,6-tetrahydrophthalimide 1
g was dissolved in 10 ml of dimethylformamide, and 0.34 g of anhydrous potassium carbonate was added and stirred at room temperature. After stirring at around 40°C for 30 minutes, 1 g of propargyl bromide was added and stirred at 50 to 60°C for 3 hours. After cooling to room temperature, the reaction solution was poured into water and extracted with ether. The ether layer was washed with water, dried over anhydrous sodium sulfate, and the concentrated residue was purified by silica gel column chromatography to obtain 0.8 g of crystals. mp136.4℃ Elemental analysis value Actual value C (%) 61.09 H (%) 4.00
N (%) 4.20 Calculated value C (%) 61.18 H (%) 4.19
N (%) 3.92 The compounds shown in Table 1 were synthesized in the same manner as in Example 1.
【表】
なお、第1表に示す化合物番号は以下の配合例
および実施例において共通に使用される。
なお、より明確に本化合物の性質を明らかにす
るために第2表の類似化合物を比較化合物とす
る。[Table] The compound numbers shown in Table 1 are commonly used in the following formulation examples and examples. In order to clarify the properties of the present compound more clearly, the similar compounds in Table 2 are used as comparative compounds.
【表】【table】
【表】
本発明化合物を実際に使用する際は、原体その
ものを散布することができ、また水和剤、乳剤、
粒剤、微粒剤、粉剤等のいずれの製剤形態のもの
でも使用できる。
本発明化合物を使用する場合、製剤形態、適用
作物、適用雑草あるいは土壌条件などによつても
異なるが、有効成分として1アール当り約0.01〜
50gの割合で用いることができるが、好ましくは
0.1〜20gである。
これらの製剤品を作成するにあたつて、固体担
体としては、たとえば鉱物質粉末(カオリン、ベ
ントナイト、クレー、モンモリロナイト、タル
ク、珪藻土、雲母、バーミキユライト、石こう、
炭酸カルシウム、りん灰石など)、植物質粉末
(大豆粉、小麦粉、木粉、タバコ粉、でんぷん、
結晶セルロースなど)、高分子化合物(石油樹脂、
ポリ塩化ビニール、ダンマルガム、ケトン樹脂な
ど)、さらにアルミナ、ワツクス類などがあげら
れる。
また、液体担体としては、たとえばアルコール
類(メチルアルコール、エチルアルコール、エチ
レングリコール、ベンジルアルコールなど)、芳
香族炭化水素類(トルエン、ベンゼン、キシレ
ン、メチルフタレンなど)、塩素化炭化水素類
(クロロホルム、四塩化炭素、モノクロロベンゼ
ンなど)、エーテル類(ジオキサン、テトラヒド
ロフランなど)、ケトン類(アセトン、メチルエ
チルケトン、シクロヘキサノンなど)、エステル
類(酢酸エチル、酢酸ブチル、エチレングリコー
ルアセテートなど)、酸アミド類(ジメチルホル
ムアミドなど)、ニトリル類(アセトニトリルな
ど)、エーテルアルコール類(エチレングリコー
ルエチルエーテルなど)および水などがあげられ
る。
乳化、分散、拡展等の目的で使用される界面活
性剤は非イオン性、陰イオン性、陽イオン性およ
び両イオン性のいずれのものも使用できる。使用
される界面活性剤の例をあげると、ポリオキシエ
チレンアルキルエーテル、ポリオキシエチレンア
ルキルアリールエーテル、ポリオキシエチレン脂
肪酸エステル、ソルビタン脂肪酸エステル、ポリ
オキシエチレンソルビタン脂肪酸エステル、オキ
シエチレンオキシプロピレンポリマー、ポリオキ
シエチレンアルキルリン酸エステル、脂肪酸塩、
アルキル硫酸エステル塩、アルキルスルホン酸
塩、アルキルアリールスルホン酸塩、アルキルリ
ン酸エステル塩、ポリオキシエチレンアルキル硫
酸エステル、第4級アンモニウム塩等であるが、
もちろんこれらのみに限定されるものではない。
また、これらの目的には必要に応じてゼラチン、
カゼイン、アルギン酸ソーダ、澱粉、寒天、ポリ
ビニルアルコールなどを補助剤として用いること
ができる。
本発明化合物を除草剤として製剤する場合、有
効成分として本発明化合物を0.1〜95%含有する
こと可能であるが、好ましくは0.5〜80%を含有
させるのがよい。
以下に本発明化合物の配合例を示す。
なお、化合物名は前記例示(第1表)の番号に
よつて示す。
配合例 1
本発明化合物(1)80重量部、アルキルサルフエー
ト3重量部、リグニンスルホン酸塩2重量部およ
びホワイトカーボン15重量部をよく粉砕混合して
水和剤を得る。
配合例 2
本発明化物(2)80重量部、ポリオキシエチレンア
ルキルアリールエーテルの50%パウダー6重量
部、リグニンスルホン酸塩2重量部およびホワイ
トカーボン12重量部をよく粉砕混合して水和剤を
得る。
配合例 3
本発明化合物(3)10重量部、乳化剤ソルポール
2680(東邦化学登録商標名)10重量部、シクロヘ
キサノン60重量部およびキシレン20重量部をよく
混合して乳剤を得る。
配合例 4
本発明化合物(5)0.5重量部、ホワイトカーボン
0.5重量部、ベントナイト35重量部およびクレー
64重量部をよく粉砕混合し、水を加えてよく練り
合わせた後、造粒乾燥して粒剤を得る。
配合例 5
本発明化合物(6)3重量部、リン酸イソプロピル
0.3重量部、クレー66.7重量部およびタルク30重
量部をよく粉砕混合して粉剤を得る。
また本発明化合物は除草剤としての効力向上を
目指し、他の除草剤との混用も可能であり、場合
によつては相乗効果を期待することもできる。こ
の例としては、たとえば2,4−ジクロルフエノ
キシ酢酸;2−メチル−4−クロルフエノキシ酪
酸;2−メチル−4−クロルフエノキシ酢酸(エ
ステル、塩類を含む)等のフエノキシ系除草剤、
2,4−ジクロルフエニル−4′ーニトロフエニル
エーテル;2,4,6−トリクロルフエニル−
4′−ニトロフエニルエーテル;2−クロロ−4−
トリフルオロメチルフエニル−3′−エトキシ−
4′−ニトロフエニルエーテル;2,4−ジクロル
フエニル−4′−ニトロ−3′−メトキシフエニルエ
ーテル;2,4−ジクロルフエニル−3′−メトキ
シカルボニル−4′−ニトロフエニルエーテル等の
ジフエニルエーテル系除草剤、2−クロル−4,
6−ビスエチルアミノ−1,3,5−トリアジ
ン;2−クロル−4エチルアミノ−6−イソプロ
ピルアミノ−1,3,5−トリアジン;2−メチ
ルチオ−4,6−ビスエチルアミノ−1,3,5
−トリアジン;2−メチルチオ−4,6−ビスイ
ソプロピルアミノ−1,3,5−トリアジン;4
−アミノ−6−ターシヤリーブチル−3−メチル
チオ−1,2,4−トリアジン−5−オン等のト
リアジン系除草剤、3−(3,4−ジクロルフエ
ニル)−1,1−ジメチルウレア;3−(3,4−
ジクロルフエニル)−1−メトキシ−1−メチル
ウレア、1−(2,2−ジメチルベンジル)−3−
p−トリルウレア、1,1−ジメチル−3−(3
−トリフルオロメチルフエニル)ウレア等の尿素
系除草剤、イソプロピル−N−(3−クロルフエ
ニル)カーバメイト;メチル−N−(3,4−ジ
クロルフエニル)カーバメイト等のカーバメイト
系除草剤、S−(4−クロルベンジル)−N,N−
ジエチルチオールカーバメイト;S−エチル−
N,N−ヘキサメチレンチオールカーバメイト;
S−エチル−N,N−ジイソブチルチオールカー
バメイト、S−エチル−N,N−ジノルマルプロ
ピルチオールカーバメイト、S−ノルマルプロピ
ル−N,N−ジノルマルプロピルチオールカーバ
メイト等のチオールカーバメイト系除草剤、3,
4−ジクロルプロピオンアニリド;N−メトキシ
メチル−2,6−ジエチル−α−クロルアセトア
ニリド;2−クロル−2′,6′−ジエチル−N−
(ブトキシメチル)−アセトアニリド;2−クロル
−2′,6′−ジエチル−N−(n−プロポキシエチ
ル)−アセトアニリド;N−クロルアセチル−N
−(2,6−ジエチルフエニル)−グリシンエチル
エステル等の酸アニリド系除草剤、2−クロル−
N−(2−エチル−6−メチルフエニル)−N−
(2−メトキシ−1−メチル)アセトアミド、5
−ブロム−3−セカンダリーブチル−6−メチル
ウラシル;3−シクロヘキシル−5,6−トリメ
チレンウラシル等のウラシル系除草剤、1,1′−
ジメチル−4,4−ビスピリジニウムクロライド
等のピリジニウム塩素系除草剤、N,N−ビス
(ホスホノメチル)−グリシン、O−エチル−O−
(2−ニトロ−5−メチルフエニル)−N−セカン
ダリーブチルホスホロアミドチオネート、S−
(2−メチル−1−ピペリジルカルボニルメチル)
O,O−ジ−n−プロピルジチオホスフエート等
のリン系除草剤、α,α,α−トリフルオロ−
2,6−ジニトロ−N,N−ジプロピル−p−ト
ルイジン等のトルイジン系除草剤、5−ターシヤ
リーブチル−3−(2,4−ジクロル−5−イソ
プロポキシフエニル−1,3,4−オキサジアゾ
リン−2−オン;3−イソプロピル−1H−2,
1,3−ベンゾチアジアジン−(4)−3H−オン−
2,2−ジオキシド、α−(β−ナフトキシ)−プ
ロピオンアニライド、4−(2,4−ジクロロベ
ンゾイル)−1,3−ジメチルピラゾール−5−
イル p−トルエンスルホネート、4′−フエニル
スルホニル−1,1,1−トリフルオロスルホノ
−o−トルイダイド、4−クロロ−5−メチルア
ミノ−2−(3−トリフルオロメチルフエニル)
ピリダジン−3(2H)−オン、1−メチル−3−
フエニル−5−(3−トリフルオロメチルフエニ
ル)−ピリジン−4(1H)−オン、2−メチル−4
−フエニルスルホニルトリフルオロメチルスルホ
アニライド、2−(3′,4′−ジクロロフエニル)−
4−メチルテトラヒドロ−1,2,4−オキサジ
アゾール−3,5−ジオン、4−クロロ−5−メ
チルアミノ−2−(3−トリフルオロメチルフエ
ニル)ピリダジン−3(2H)−オンなどがあげら
れるが、これらに限られるものではない。
さらに本発明化合物は必要に応じて殺虫剤、殺
線虫剤、殺菌剤、植物生長調節剤および肥料等と
の混用も可能である。
次に除草剤としての実施例にあげ、本発明をさ
らに詳細に説明するが、除草剤としての以下の各
実施例において栽培植物に対する薬害と雑草に対
する効力との評価はすべて以下に述べる基準にし
たがい、0から5までの整数による評価値で表わ
した。調査時点に枯れ残つた植物体の地上部の生
重量をはかり、無処理区の植物体の生重量と比較
したときの比率(%)を計算する。栽培植物と雑
草について下表のような基準にもとづき、薬害と
除草効力を0から5までの数字で評価した。栽培
植物に対する評価値0または1あるいは雑草に対
する評価値5または4は一般に妥当な栽培植物保
護効果、あるいは雑草防除効果とみなされる。
なお、水稲試験の場合のみ、植物体の乾燥重量
により評価値を算出している。[Table] When actually using the compound of the present invention, the raw material itself can be sprayed, and hydrating powders, emulsions,
Any formulation form such as granules, fine granules, or powders can be used. When using the compound of the present invention, the active ingredient is approximately 0.01 to 10% per are, although it varies depending on the formulation form, applicable crops, applicable weeds, soil conditions, etc.
It can be used at a rate of 50g, but preferably
It is 0.1-20g. In preparing these pharmaceutical products, solid carriers such as mineral powders (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum,
calcium carbonate, apatite, etc.), vegetable powders (soybean flour, wheat flour, wood flour, tobacco flour, starch,
crystalline cellulose, etc.), polymer compounds (petroleum resin,
(polyvinyl chloride, dammargum, ketone resin, etc.), alumina, waxes, etc. Examples of liquid carriers include alcohols (methyl alcohol, ethyl alcohol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xylene, methylphthalene, etc.), and chlorinated hydrocarbons (chloroform, carbon chloride, monochlorobenzene, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, etc.), acid amides (dimethylformamide, etc.) ), nitriles (such as acetonitrile), ether alcohols (such as ethylene glycol ethyl ether), and water. The surfactant used for the purpose of emulsification, dispersion, spreading, etc. may be nonionic, anionic, cationic, or amphoteric. Examples of surfactants used include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, oxyethylene oxypropylene polymer, polyoxy Ethylene alkyl phosphate ester, fatty acid salt,
Alkyl sulfate salts, alkyl sulfonates, alkylaryl sulfonates, alkyl phosphate salts, polyoxyethylene alkyl sulfate esters, quaternary ammonium salts, etc.
Of course, it is not limited to these.
In addition, gelatin,
Casein, sodium alginate, starch, agar, polyvinyl alcohol, etc. can be used as adjuvants. When the compound of the present invention is formulated as a herbicide, the compound of the present invention can be contained as an active ingredient in an amount of 0.1 to 95%, preferably 0.5 to 80%. Examples of blending the compounds of the present invention are shown below. Note that the compound names are indicated by the numbers in the above examples (Table 1). Formulation Example 1 80 parts by weight of the compound (1) of the present invention, 3 parts by weight of alkyl sulfate, 2 parts by weight of lignin sulfonate and 15 parts by weight of white carbon are thoroughly ground and mixed to obtain a wettable powder. Formulation Example 2 80 parts by weight of the compound of the present invention (2), 6 parts by weight of 50% polyoxyethylene alkylaryl ether powder, 2 parts by weight of lignin sulfonate and 12 parts by weight of white carbon were thoroughly ground and mixed to form a wettable powder. obtain. Formulation example 3 10 parts by weight of the compound of the present invention (3), emulsifier Solpol
10 parts by weight of 2680 (registered trademark of Toho Chemical), 60 parts by weight of cyclohexanone, and 20 parts by weight of xylene are thoroughly mixed to obtain an emulsion. Formulation example 4 0.5 parts by weight of the present compound (5), white carbon
0.5 parts by weight, 35 parts by weight of bentonite and clay
After thoroughly grinding and mixing 64 parts by weight, adding water and kneading well, the mixture is granulated and dried to obtain granules. Formulation example 5 3 parts by weight of the compound (6) of the present invention, isopropyl phosphate
0.3 parts by weight, 66.7 parts by weight of clay, and 30 parts by weight of talc are thoroughly ground and mixed to obtain a powder. Furthermore, the compound of the present invention can be used in combination with other herbicides in order to improve its effectiveness as a herbicide, and in some cases a synergistic effect can be expected. Examples include phenoxy herbicides such as 2,4-dichlorophenoxyacetic acid; 2-methyl-4-chlorophenoxybutyric acid; 2-methyl-4-chlorophenoxyacetic acid (including esters and salts);
2,4-dichlorophenyl-4' nitrophenyl ether; 2,4,6-trichlorophenyl-
4'-nitrophenyl ether; 2-chloro-4-
Trifluoromethylphenyl-3'-ethoxy-
Diphenyl such as 4'-nitrophenyl ether; 2,4-dichlorophenyl-4'-nitro-3'-methoxyphenyl ether; 2,4-dichlorophenyl-3'-methoxycarbonyl-4'-nitrophenyl ether Ether herbicide, 2-chloro-4,
6-bisethylamino-1,3,5-triazine; 2-chloro-4ethylamino-6-isopropylamino-1,3,5-triazine; 2-methylthio-4,6-bisethylamino-1,3 ,5
-triazine; 2-methylthio-4,6-bisisopropylamino-1,3,5-triazine; 4
- Triazine herbicides such as amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5-one, 3-(3,4-dichlorophenyl)-1,1-dimethylurea; 3- (3,4-
dichlorophenyl)-1-methoxy-1-methylurea, 1-(2,2-dimethylbenzyl)-3-
p-Tolylurea, 1,1-dimethyl-3-(3
urea-based herbicides such as -trifluoromethylphenyl)urea, isopropyl-N-(3-chlorophenyl)carbamate; carbamate-based herbicides such as methyl-N-(3,4-dichlorophenyl)carbamate, S-(4- Chlorbenzyl)-N,N-
Diethylthiol carbamate; S-ethyl-
N,N-hexamethylenethiol carbamate;
Thiol carbamate herbicides such as S-ethyl-N,N-diisobutylthiolcarbamate, S-ethyl-N,N-dinormalpropylthiolcarbamate, S-normalpropyl-N,N-dinormalpropylthiolcarbamate, 3.
4-dichloropropionanilide; N-methoxymethyl-2,6-diethyl-α-chloroacetanilide; 2-chloro-2',6'-diethyl-N-
(Butoxymethyl)-acetanilide; 2-chloro-2',6'-diethyl-N-(n-propoxyethyl)-acetanilide; N-chloroacetyl-N
-Acid anilide herbicides such as (2,6-diethylphenyl)-glycine ethyl ester, 2-chloro-
N-(2-ethyl-6-methylphenyl)-N-
(2-methoxy-1-methyl)acetamide, 5
-bromo-3-sec-butyl-6-methyluracil; uracil herbicides such as 3-cyclohexyl-5,6-trimethyleneuracil, 1,1'-
Pyridinium chlorine herbicides such as dimethyl-4,4-bispyridinium chloride, N,N-bis(phosphonomethyl)-glycine, O-ethyl-O-
(2-Nitro-5-methylphenyl)-N-secondary butylphosphoroamidothionate, S-
(2-methyl-1-piperidylcarbonylmethyl)
Phosphorus herbicides such as O,O-di-n-propyldithiophosphate, α,α,α-trifluoro-
Toluidine herbicides such as 2,6-dinitro-N,N-dipropyl-p-toluidine, 5-tert-butyl-3-(2,4-dichloro-5-isopropoxyphenyl-1,3,4- Oxadiazolin-2-one; 3-isopropyl-1H-2,
1,3-Benzothiadiazin-(4)-3H-one-
2,2-dioxide, α-(β-naphthoxy)-propionanilide, 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazole-5-
p-toluenesulfonate, 4'-phenylsulfonyl-1,1,1-trifluorosulfono-o-toluidide, 4-chloro-5-methylamino-2-(3-trifluoromethylphenyl)
Pyridazin-3(2H)-one, 1-methyl-3-
Phenyl-5-(3-trifluoromethylphenyl)-pyridin-4(1H)-one, 2-methyl-4
-Phenylsulfonyltrifluoromethylsulfoanilide, 2-(3',4'-dichlorophenyl)-
4-methyltetrahydro-1,2,4-oxadiazole-3,5-dione, 4-chloro-5-methylamino-2-(3-trifluoromethylphenyl)pyridazin-3(2H)-one, etc. Examples include, but are not limited to. Furthermore, the compound of the present invention can be used in combination with insecticides, nematicides, fungicides, plant growth regulators, fertilizers, etc., if necessary. Next, the present invention will be explained in more detail with reference to Examples as herbicides. In each of the following Examples as herbicides, the evaluation of phytotoxicity to cultivated plants and efficacy against weeds was all in accordance with the criteria described below. , expressed as an evaluation value using an integer from 0 to 5. The fresh weight of the above-ground parts of the plants that remained withered at the time of the survey was measured, and the ratio (%) compared to the fresh weight of the plants in the untreated area was calculated. Cultivated plants and weeds were evaluated for chemical damage and herbicidal efficacy using numbers from 0 to 5 based on the criteria shown in the table below. An evaluation value of 0 or 1 for cultivated plants or an evaluation value of 5 or 4 for weeds is generally considered to be an appropriate cultivated plant protection effect or weed control effect. In addition, only in the case of the paddy rice test, the evaluation value is calculated based on the dry weight of the plant.
【表】
実施例 2
発芽後茎葉処理効力比較試験
直径10cm、高さ10cmの円筒プラスチツクビーカ
ーに畑地土壌を詰め、ヒエ、カラスムギ、ノハラ
ガラシ、イチビの雑草種子を播種した。覆土後、
温室内で2週間育生したあと、所定量の薬剤をハ
ンドスプレヤーで植物体の上方から茎葉部全面に
処理した。薬剤処理後、さらに3週間温室内で育
生したあと、各植物について除草効力を調査し
た。
その結果を第3表に示す。なお、処理薬剤は乳
剤に製剤し、所定量を水(展着剤を含む)に分散
させ、1アールあたり5散布の割合で試験を行
なつた。[Table] Example 2 Post-germination foliage treatment efficacy comparative test A cylindrical plastic beaker with a diameter of 10 cm and a height of 10 cm was filled with field soil, and weed seeds of Japanese barnyard grass, oat, wild mustard, and Japanese yam were sown. After covering with soil,
After growing in a greenhouse for two weeks, a predetermined amount of the chemical was applied to the entire stem and leaves from the top of the plant using a hand sprayer. After the chemical treatment, each plant was grown in a greenhouse for another three weeks, and then the herbicidal efficacy of each plant was investigated. The results are shown in Table 3. The processing agent was formulated into an emulsion, a predetermined amount was dispersed in water (including a spreading agent), and the test was conducted at a rate of 5 sprays per are.
【表】【table】
【表】
実施例 3
トウモロコシ除草試験(茎葉処理)
たて35cm、よこ25cm、たかさ10cmのプラスチツ
クトレーに畑地土壌を詰め、トウモロコシ、イチ
ビ、ヒマワリ、エビスグサ、マルバアサガオ、ノ
ハラガラシ、ハコベおよびエノコログサを播種
し、温室内で2週間育成したあと、たて50cm、よ
こ100cm、たかさ40cmの枠内にこのトレーを2個
並べ、植物体の上方から小型噴霧器で各薬剤の所
定量を枠内全面に茎葉処理した。薬剤散布後さら
に3週間温室内で育生したあと、各植物ごとに薬
害あるいは除草効力を調査した。その結果を第4
表に示す。なお処理薬剤は配合例3の処方に準じ
て作つた乳剤を使用し、展着剤を加えた水25mlに
乳化させたものを供試した。薬剤処理時の植物の
大きさは種類によつて異なるが、ほぼ本葉1〜3
葉期で草丈2〜20cmであつた。[Table] Example 3 Corn weeding test (stem and foliage treatment) Field soil was packed into plastic trays measuring 35 cm in height, 25 cm in width, and 10 cm in height, and corn, Japanese croaker, sunflower, Ebisu grass, Maruba morning glory, Wildflower, chickweed, and Japanese foxtail were sown. After growing in a greenhouse for two weeks, two of these trays were arranged in a frame measuring 50 cm in length, 100 cm in width, and 40 cm in height, and a small sprayer was used from above the plant to spray a predetermined amount of each chemical over the entire frame. The stems and leaves were treated. After being grown in a greenhouse for an additional three weeks after spraying the chemicals, each plant was examined for chemical damage or herbicidal efficacy. The result is the fourth
Shown in the table. The processing agent used was an emulsion prepared according to the recipe in Formulation Example 3, and the emulsion was emulsified in 25 ml of water to which a spreading agent was added. The size of plants when treated with chemicals varies depending on the species, but approximately 1 to 3 true leaves.
The plant height was 2 to 20 cm at the leaf stage.
【表】
実施例 4
畑地発芽前土壌処理効力比較試験
直径10cm、高さ10cmの円筒プラスチツクビーカ
ーに畑地土壌を詰め、トウモロコシ、ワタ、ダイ
ズの作物種子およびアサガオ、イチビ、セイバン
モロコシ、エノコログサの雑草種子を播種した。
覆土後、所定量の原体を乳剤にし、水で希釈し
ハンドスプレヤーにて土壌処理した。
その後、温室内にて育生し、処理後20日目に除
草効力を観察し、その結果を第5表に示す。[Table] Example 4 Pre-emergence soil treatment efficacy comparison test for upland fields A cylindrical plastic beaker with a diameter of 10 cm and a height of 10 cm was filled with upland soil, and crop seeds of corn, cotton, and soybean and weed seeds of morning glory, Japanese yam, Seiban sorghum, and foxtail were added. was sown. After covering with soil, a predetermined amount of the raw material was made into an emulsion, diluted with water, and the soil was treated with a hand sprayer. Thereafter, the plants were grown in a greenhouse, and the herbicidal efficacy was observed on the 20th day after treatment. The results are shown in Table 5.
【表】【table】
【表】
実施例 5
発芽前土壌処理試験
たて35cm、よこ25cm、たかさ15cmのプラスチツ
クトレーに畑地土壌を詰め、マルバアサガオ、イ
チビ、エビスグサ、セイバンモロコシおよびトウ
モロコシを播種した。
所定量の水和剤を水に分散させ、1アールあた
り5散布の割合でトレーの上方から小型噴霧器
で土壌全面にスプレー処理した。
処理後、20日間温室に置き、薬害および除草効
力を調査した。
その結果を第6表に示す。[Table] Example 5 Pre-germination soil treatment test A plastic tray measuring 35 cm in length, 25 cm in width, and 15 cm in height was filled with field soil and sown with morning glory, Japanese sorghum, Ebisugusa, Seiban sorghum, and corn. A predetermined amount of the hydrating agent was dispersed in water, and the entire surface of the soil was sprayed from above the tray using a small sprayer at a rate of 5 sprays per are. After treatment, the plants were placed in a greenhouse for 20 days and their phytotoxicity and herbicidal efficacy were investigated. The results are shown in Table 6.
【表】
実施例 6
湛水処理
1/5000aのワグネルポツトに各種の雑草種子
を含んだ水田土壌を詰め、水深が4cmになるまで
水を加えたあと、3.5葉期のイネ苗およびウリカ
ワ塊茎を移植して2日間温室で育生する。乳剤に
製剤した所定量の薬剤を水に分散させ、1アール
あたり10の割合でポツト内に潅注処理した。さ
らに3週間温室内で育生したあと各植物について
除草効力を調査した。なお、この土壌中にはタイ
ヌビエ、ホタルイおよび広葉雑草(コナギ、アゼ
ナ、キカシグサなど)の種子を混入しておいた。
上記3種の調査結果を第7表に示す。[Table] Example 6 Flooding Treatment A 1/5000a Wagner pot was filled with paddy soil containing various weed seeds, and after adding water to a depth of 4 cm, rice seedlings at the 3.5 leaf stage and Urikawa tubers were transplanted. Then grow in a greenhouse for 2 days. A predetermined amount of the drug formulated into an emulsion was dispersed in water and irrigated into the pot at a rate of 10 per are. After growing in the greenhouse for an additional three weeks, the herbicidal efficacy of each plant was investigated. The soil was mixed with seeds of Japanese millet, firefly, and broad-leaved weeds (Japanese grass, Japanese azalea, Japanese grass, etc.). Table 7 shows the results of the above three types of investigations.
Claims (1)
3〜4のアルケニル基または炭素数3〜4のアル
キニル基を表わす。ただし、Rがイソプロピル基
である場合は含まれない。〕 で示されるN−フエニルテトラヒドロフタルイミ
ド誘導体。 2 一般式 RX 〔式中、Rは炭素数1〜4のアルキル基、炭素数
3〜4のアルケニル基または炭素数3〜4のアル
キニル基を表わす。ただし、Rがイソプロピル基
である場合は含まれない。〕 で示されるハロゲン化合物とN−(4−クロロ−
2−フルオロ−5−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とを塩基
の存在下で反応させることを特徴とする一般式 〔式中、Rは前述のとおりである。〕 で示されるN−フエニルテトラヒドロフタルイミ
ド誘導体の製造法。 3 一般式 〔式中、Rは炭素数1〜4のアルキル基、炭素数
3〜4のアルケニル基または炭素数3〜4のアル
キニル基を表わす。ただし、Rがイソプロピル基
である場合は含まれない。〕 で示されるN−フエニルテトラヒドロフタルイミ
ド誘導体を有効成分として含有することを特徴と
する除草剤。 4 有効成分がN−(4−クロロ−2−フルオロ
−5−プロパルギルオキシフエニル)−3,4,
5,6−テトラヒドロフタルイミドである特許請
求の範囲第3項に記載のトウモロコシ用選択性除
草剤。[Claims] 1. General formula [In the formula, R represents an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, or an alkynyl group having 3 to 4 carbon atoms. However, it is not included when R is an isopropyl group. ] N-phenyltetrahydrophthalimide derivative represented by these. 2 General Formula RX [In the formula, R represents an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, or an alkynyl group having 3 to 4 carbon atoms. However, it is not included when R is an isopropyl group. ] The halogen compound shown by and N-(4-chloro-
2-fluoro-5-hydroxyphenyl)-3,
General formula characterized by reacting 4,5,6-tetrahydrophthalimide in the presence of a base [In the formula, R is as described above.] ] A method for producing an N-phenyltetrahydrophthalimide derivative shown in the following. 3 General formula [In the formula, R represents an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, or an alkynyl group having 3 to 4 carbon atoms. However, it is not included when R is an isopropyl group. ] A herbicide characterized by containing an N-phenyltetrahydrophthalimide derivative as an active ingredient. 4 The active ingredient is N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-3,4,
The selective herbicide for corn according to claim 3, which is 5,6-tetrahydrophthalimide.
Priority Applications (29)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13804481A JPS5838256A (en) | 1981-09-01 | 1981-09-01 | N-phenyltetrahydrophthalimide derivative, its preparation and herbicide containing the same as active constituent |
US06/360,997 US4484940A (en) | 1981-09-01 | 1982-03-23 | Tetrahydrophthalimides, and their production and use as herbicides |
US06/360,999 US4484941A (en) | 1981-09-01 | 1982-03-23 | Tetrahydrophthalimides, and their production and use as herbicides |
AU81930/82A AU550845B2 (en) | 1981-03-30 | 1982-03-25 | Tetrahydrophthalimides and their starting compounds |
DE8282102565T DE3266288D1 (en) | 1981-03-30 | 1982-03-26 | Tetrahydrophthalimides, and their production and use |
DK140382A DK154212C (en) | 1981-03-30 | 1982-03-26 | TETRAHYDROPHTHALIMIDES, A HERBICID PREPARATION CONTAINING THESE, AND THEIR USE FOR THE FERTILIZATION OF WEEDS |
EP82102565A EP0061741B1 (en) | 1981-03-30 | 1982-03-26 | Tetrahydrophthalimides, and their production and use |
HU95382A HU187451B (en) | 1981-03-30 | 1982-03-29 | Herbicide compositions containing tetrahydro-phtalimide derivatives as active agents, and process for producing the active agents |
CA000399608A CA1164467A (en) | 1981-09-01 | 1982-03-29 | Tetrahydrophthalimides, and their production and use |
AR28891182A AR230424A1 (en) | 1981-03-30 | 1982-03-29 | NEW DERIVATIVES OF 2-FLUOR-4-CHLORINE OR 5-HYDROXY ANILINE NITROBENZENE PROCEDURE FOR PREPARING THEM; N- (2-FLUOR-HALO-5-PHENYL) 3,4,5,6-TETRAHYDROPHTHALIMIDES OBTAINED FROM THESE DERIVATIVES PROCEDURES FOR ITS PREPARATION |
CA000399595A CA1164002A (en) | 1981-09-01 | 1982-03-29 | Tetrahydrophthalimides, and their production and use |
SU823415050A SU1611206A3 (en) | 1981-03-30 | 1982-03-29 | Method of control of unwanted vegetation |
KR8201345A KR890000766B1 (en) | 1981-03-30 | 1982-03-29 | Process for preparing of tetrahydrophthalimides |
ES510917A ES510917A0 (en) | 1981-03-30 | 1982-03-29 | A PROCEDURE FOR THE PREPARATION OF TETRAHIDROFTALIMIDAS. |
MX793482A MX155119A (en) | 1981-03-30 | 1982-03-30 | PROCEDURE FOR THE PREPARATION OF N- (2-FLUORO-4-HALO-5-PHENYL-SUBSTITUTED) -3,4,5,6-TETRA-HYDROPHTHALIMIDES |
BG5602082A BG40644A3 (en) | 1981-03-30 | 1982-03-30 | Herbicide means and method for protection from weeds |
PL23570882A PL133782B1 (en) | 1981-03-30 | 1982-03-30 | Herbicide and process for preparing n-/4-halo-2-fluoro-5-substituted phenyl/-3,4,5,6-tetrahydrophtalimide |
BR8201807A BR8201807A (en) | 1981-03-30 | 1982-03-30 | COMPOUND INTERMEDIATE COMPOUNDS FOR THE SAME PROCESSES FOR ITS RESPECTIVE PREPARATION HERBICIDE COMPOSITION PROCESS TO CONTROL WEEDS AND USE OF A COMPOUND |
CA000428781A CA1186337A (en) | 1981-09-01 | 1983-05-24 | Intermediates for producing tetrahydrophthalimides |
CA000429249A CA1186338A (en) | 1981-09-01 | 1983-05-30 | Starting materials for producing tetrahydrophthalimides |
US06/651,877 US5030760A (en) | 1981-09-01 | 1984-09-18 | Tetrahydrophthalimides, and their production and use |
US06/903,830 US4736068A (en) | 1981-09-01 | 1986-09-03 | Tetrahydrophthalimides and their production and use as herbicides |
MX922587A MX9225A (en) | 1981-09-01 | 1987-02-10 | PROCEDURE FOR PREPARING N- (2-FLUORO-4-HALO-5-PHENYL SUBSTITUTED) -3,4,5,6 TETRAHIDROFTALIMIDAS AND COMPOUND OBTAINED. |
DK591387A DK159845C (en) | 1981-03-30 | 1987-11-11 | 1-AMINO-2-FLUORO-4-HALOGENE BENZEN DERIVATIVES AND A PROCEDURE FOR PREPARING THEREOF |
US07/130,522 US4835324A (en) | 1981-09-01 | 1987-12-09 | Tetrahydrophthalimides, and their production and use |
MY8800096A MY8800096A (en) | 1981-03-30 | 1988-12-30 | Tetrahydro phthalimides and their production and use |
DK142990A DK163818C (en) | 1981-03-30 | 1990-06-11 | 4-FLUORO-2-HALOGEN-5-NITROPHENOLS AND A PROCEDURE FOR PREPARING THEREOF |
DK143090A DK160487C (en) | 1981-03-30 | 1990-06-11 | N- (2-FLUORO-4-HALOGEN-5-HYDROXYPHENYL) -3,4,5,6-TETRAHYDROPHTHALIMIDE COMPOUNDS AND A PROCEDURE FOR PREPARING THEREOF |
US07/650,943 US5191105A (en) | 1981-09-01 | 1991-02-05 | Tetrahydrophthalimides, and their production and use as herbicides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13804481A JPS5838256A (en) | 1981-09-01 | 1981-09-01 | N-phenyltetrahydrophthalimide derivative, its preparation and herbicide containing the same as active constituent |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5838256A JPS5838256A (en) | 1983-03-05 |
JPH0247464B2 true JPH0247464B2 (en) | 1990-10-19 |
Family
ID=15212693
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP13804481A Granted JPS5838256A (en) | 1981-03-30 | 1981-09-01 | N-phenyltetrahydrophthalimide derivative, its preparation and herbicide containing the same as active constituent |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPS5838256A (en) |
MX (1) | MX9225A (en) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5373557A (en) * | 1976-12-13 | 1978-06-30 | Mitsubishi Chem Ind Ltd | 3,4,5,6,-tetrahydrophthalimide and herbicide containing the same |
JPS5419965A (en) * | 1977-07-12 | 1979-02-15 | Mitsubishi Chem Ind Ltd | Preparation of n-substituted phenyl-3,4,5,6-tetrahydro-phthalimide |
JPS55139305A (en) * | 1979-04-13 | 1980-10-31 | Mitsubishi Chem Ind Ltd | Herbicide |
JPS55139359A (en) * | 1979-04-13 | 1980-10-31 | Mitsubishi Chem Ind Ltd | Tetrahydrophthalimides, and herbicide containing compound as effective component |
-
1981
- 1981-09-01 JP JP13804481A patent/JPS5838256A/en active Granted
-
1987
- 1987-02-10 MX MX922587A patent/MX9225A/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5373557A (en) * | 1976-12-13 | 1978-06-30 | Mitsubishi Chem Ind Ltd | 3,4,5,6,-tetrahydrophthalimide and herbicide containing the same |
JPS5419965A (en) * | 1977-07-12 | 1979-02-15 | Mitsubishi Chem Ind Ltd | Preparation of n-substituted phenyl-3,4,5,6-tetrahydro-phthalimide |
JPS55139305A (en) * | 1979-04-13 | 1980-10-31 | Mitsubishi Chem Ind Ltd | Herbicide |
JPS55139359A (en) * | 1979-04-13 | 1980-10-31 | Mitsubishi Chem Ind Ltd | Tetrahydrophthalimides, and herbicide containing compound as effective component |
Also Published As
Publication number | Publication date |
---|---|
MX9225A (en) | 1993-09-01 |
JPS5838256A (en) | 1983-03-05 |
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