JPH04145078A - Pyrroledicarboxylic acid derivative and herbicide - Google Patents
Pyrroledicarboxylic acid derivative and herbicideInfo
- Publication number
- JPH04145078A JPH04145078A JP26523290A JP26523290A JPH04145078A JP H04145078 A JPH04145078 A JP H04145078A JP 26523290 A JP26523290 A JP 26523290A JP 26523290 A JP26523290 A JP 26523290A JP H04145078 A JPH04145078 A JP H04145078A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- lower alkyl
- herbicide
- 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.)
- Pending
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 22
- 239000004009 herbicide Substances 0.000 title claims abstract description 15
- OEUSNWDYXDEXDR-UHFFFAOYSA-N 1h-pyrrole-2,3-dicarboxylic acid Chemical class OC(=O)C=1C=CNC=1C(O)=O OEUSNWDYXDEXDR-UHFFFAOYSA-N 0.000 title claims description 8
- -1 2,6-diethylphenyl Chemical group 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 60
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 24
- 239000003960 organic solvent Substances 0.000 abstract description 10
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 17
- 239000000843 powder Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000012044 organic layer 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
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- 239000002344 surface layer Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 244000296912 Ageratum conyzoides Species 0.000 description 2
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 2
- 235000005476 Digitaria cruciata Nutrition 0.000 description 2
- 235000006830 Digitaria didactyla Nutrition 0.000 description 2
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 244000025670 Eleusine indica Species 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- 241000254158 Lampyridae Species 0.000 description 2
- 235000000391 Lepidium draba Nutrition 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 240000001341 Reynoutria japonica Species 0.000 description 2
- 235000018167 Reynoutria japonica Nutrition 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 125000000304 alkynyl group Chemical group 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
- 238000009835 boiling Methods 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 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
- 239000002023 wood Substances 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical group CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 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
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- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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- 235000010469 Glycine max Nutrition 0.000 description 1
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- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
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- 229920002472 Starch Polymers 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
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- 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
- 238000007112 amidation reaction Methods 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- QKZIVVMOMKTVIK-UHFFFAOYSA-M anilinomethanesulfonate Chemical group [O-]S(=O)(=O)CNC1=CC=CC=C1 QKZIVVMOMKTVIK-UHFFFAOYSA-M 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
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- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000004983 dialkoxyalkyl group Chemical group 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 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
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- WKHJZIRDAONVML-UHFFFAOYSA-N dichloromethane;tetrachloromethane Chemical compound ClCCl.ClC(Cl)(Cl)Cl WKHJZIRDAONVML-UHFFFAOYSA-N 0.000 description 1
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 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
- 239000003350 kerosene Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 239000003209 petroleum derivative 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
- 230000008654 plant damage Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000004424 polypyridyl Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane 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
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】 発明の目的 産業上の利用分野 本発明は、新規なピロールカルホン酸銹導体に関する。[Detailed description of the invention] Purpose of invention Industrial applications The present invention relates to a novel pyrrolecarphonic acid conductor.
より詳しくは、後記一般式(I)て表わされる新規なピ
ロールジカルボン酸誘導体、ならひに当該訪導体を活性
成分として含有することを特徴とする除草剤に関するも
のである。し・たかって、本発明は化学工業ならひに農
業、特に農薬製造分野て有用である。More specifically, the present invention relates to a herbicide characterized by containing a novel pyrrole dicarboxylic acid derivative represented by the general formula (I) below as an active ingredient. Therefore, the present invention is useful in the chemical industry, agriculture, and especially in the agricultural chemical manufacturing field.
従来の技術
これまて、後記−数式(I)の化合物に近似化学構造を
有する化合物はいくつか知られている。BACKGROUND OF THE INVENTION Several compounds have been known that have chemical structures similar to those of formula (I) below.
例えば、下記の(II)式化合物かイキリス特許第21
94788号公報、(m)式化合物かイキリス特許第2
21480号公報などに開示され、これらの化合物か除
草活性を有するとの記載かある。For example, the following formula (II) compound or Ikiris Patent No. 21
Publication No. 94788, Formula (m) compound or Ikiris Patent No. 2
It is disclosed in Japanese Patent No. 21480, etc., and there is a description that these compounds have herbicidal activity.
(II )式化合物
(R,R’は独立してアルケニル基、アルキニル基ある
いはハロゲン化アルキル基を示しX l 、 X 2は
それぞれ独立して水素原子、ハロゲン原子、アルキル基
、ヒドロキシル基、アルコキシ基、モノもしくはジアル
コキシアルキル基、ジフルオロメトロキシ基、アルキル
チオ基、アミノ基、モノもしくはジアルキルアミノ基、
シアノ基、ニトロ基を示し、R2は水素原子、ヒドロキ
シメチル基、ジアルキルホウ素基、アルキルカルボニル
基、アルキルカルボニルオキシアルキル基、アルキルオ
キシカルホニルチオ基、フェニルオキシカルボニルチオ
基を示す。)
(m)式化合物
(RおよびR1は、おのおの独立してアルキル基、モノ
もしくはポリハロゲン化アルキル基、アルケニル基、ア
ルキニル基を示し、AはC1〜C3アルキル基を示し、
Jは窒素原子を含むペテロ環を示し R2は水素原子、
ヒドロキシメチル基、ジアルキルホウ素基、アルキルカ
ルボニル基を示す。)
しかしなから、本発明のビロールジカルボン酸誘導体は
これまてに文献に記載されておらず、新規化合物である
。Compounds of formula (II) (R and R' independently represent an alkenyl group, an alkynyl group, or a halogenated alkyl group; , mono- or dialkoxyalkyl group, difluorometholoxy group, alkylthio group, amino group, mono- or dialkylamino group,
A cyano group or a nitro group is represented, and R2 represents a hydrogen atom, a hydroxymethyl group, a dialkylboron group, an alkylcarbonyl group, an alkylcarbonyloxyalkyl group, an alkyloxycarbonylthio group, or a phenyloxycarbonylthio group. ) Compound of formula (m) (R and R1 each independently represent an alkyl group, a mono- or polyhalogenated alkyl group, an alkenyl group, an alkynyl group, A represents a C1-C3 alkyl group,
J represents a petro ring containing a nitrogen atom, R2 is a hydrogen atom,
Indicates a hydroxymethyl group, dialkylboron group, and alkylcarbonyl group. ) However, the pyrroldicarboxylic acid derivative of the present invention has not been described in any literature and is a new compound.
発明か解決しようとする課題
本発明化合物に化学構造上近似の化合物4例えば2−メ
チル−5−ピリジルピロールカルボン酸誘導体は後記の
試験例に示したとおり除草効果と薬害の点から除草剤と
して実用上必ずしも満足すべきものてはない。Problems to be Solved by the Invention Compounds 4 that are chemically structurally similar to the compounds of the present invention, such as 2-methyl-5-pyridylpyrrole carboxylic acid derivatives, are practical as herbicides in terms of herbicidal effects and phytotoxicity, as shown in the test examples below. The above is not necessarily satisfactory.
本発明はこれらの公知化合物に代わり、水稲用除草剤お
よび畑作用除草剤としてより優れた除草活性と安全性を
有する新規な除草剤を提供することにある。The object of the present invention is to provide a new herbicide having superior herbicidal activity and safety as a paddy rice herbicide and an upland herbicide in place of these known compounds.
発明の構成
課題を解決するための手段
本発明者らは、上記の目的を達成するために数多くのピ
ロールシカルホン酸類を合成し、それらの有用性につい
て鋭意検討した。その結果、後記ビロールジカルボン酸
誘導体か文献未記載の新規化合物てあり、高い除草活性
と安全性を有し、上記目的を達成するものであることを
見出した。Means for Solving the Constituent Problems of the Invention In order to achieve the above object, the present inventors synthesized a large number of pyrrole sicaphonic acids and conducted extensive studies on their usefulness. As a result, it was discovered that the pyrroldicarboxylic acid derivative described below is a new compound that has not been described in any literature, has high herbicidal activity and safety, and achieves the above objectives.
したかって、第1の本発明の要旨とするところは次の一
般式(I)
(式中、R,は水素原子、低級アルキル基、フェニル低
級アルキル基を示し、R2はヒドロキシル基、低級アル
コキシ基、低級アルキルチオ基、てもよい水素原子、低
級アルキル基、2.6−シエチルフエニル基を示す。)
を示し、R1はピリジル基、チエニル基、フリル基、ト
リフルオロメチル基を示す。〕て表わされるビロールジ
カルボン酸誘導体にある。Therefore, the gist of the first invention is represented by the following general formula (I) (wherein R represents a hydrogen atom, a lower alkyl group, or a phenyl lower alkyl group, and R2 represents a hydroxyl group or a lower alkoxy group). , lower alkylthio group, optional hydrogen atom, lower alkyl group, 2,6-ethylphenyl group)
and R1 represents a pyridyl group, a thienyl group, a furyl group, or a trifluoromethyl group. ] It is a pyrroldicarboxylic acid derivative represented by
低級アルコキシ基のアルキル基および低級アルキル基と
は直鎖状てあっても分岐状てあってもよい。また、低級
とは炭素数1〜6を意味する。The alkyl group of the lower alkoxy group and the lower alkyl group may be linear or branched. Moreover, lower means carbon number 1-6.
また第2の本発明の要旨とするところは、上記−数式(
I )のピロールジカルボン酸誘導体を活性成分として
含有することを特徴とする除草剤にある。Furthermore, the gist of the second invention is as follows:
A herbicide characterized by containing the pyrrole dicarboxylic acid derivative of I) as an active ingredient.
次に本発明の一般式(I)の化合物の代表的ななお、本
発明化合物陥は以下の実施例、試験例ても参照される。Next, the following examples and test examples are also referred to for typical effects of the compounds of the present invention of the general formula (I).
第 表 i月 本発明の一般式(1)の化合物は、新規化合物である。No. table i month The compound of general formula (1) of the present invention is a new compound.
そして、この一般式(I)の化合物は水田あるいは畑作
地における各種雑草を防除するための活性成分として作
用する。The compound of general formula (I) acts as an active ingredient for controlling various weeds in paddy fields or upland fields.
次に本発明化合物の製造法について説明する。Next, a method for producing the compound of the present invention will be explained.
実施例 本発明化合物の製造法
第1の本発明による一般式(I)の化合物の製造は、次
−に説明する3つの方法、すなわち方法(A)、方法(
B)、または方法(C)によって行い得る。Examples Manufacturing method of the compound of the present invention The first method of manufacturing the compound of general formula (I) according to the present invention can be carried out by the following three methods, namely, method (A), method (
B) or method (C).
方法(A)
一般式(I)てR1か水素原子てR2か低級アルコキシ
基の化合物(■)′は、一般式(TV)て示されるアセ
チレンジカルボン酸エステル誘導体に一般式(V)て示
されるN−アシルフェニルクリシン誘導体を反応させる
ことにより製造てきる。Method (A) A compound (■)' in which R1, a hydrogen atom, and R2 is a lower alkoxy group in the general formula (I) is an acetylene dicarboxylic acid ester derivative represented by the general formula (TV), and the compound (■)' is represented by the general formula (V). It can be produced by reacting N-acylphenylchrysine derivatives.
(TV)
(V)
■
(式中、R3は前記に同しである。)
この環化反応は通常有機溶媒中て行う。使用できる溶媒
としてはベンゼン、トルエン、キシレンなとの炭化水素
類、無水酢酸、無水プロピオン酸などのカルボン酸無水
物なとてあり、好ましくは無水酢酸である。反応温度は
通常室温から溶媒の沸点まてであるか、好ましくは10
0℃以上である。(TV) (V) (In the formula, R3 is as defined above.) This cyclization reaction is usually carried out in an organic solvent. Usable solvents include hydrocarbons such as benzene, toluene and xylene, and carboxylic acid anhydrides such as acetic anhydride and propionic anhydride, with acetic anhydride being preferred. The reaction temperature is usually from room temperature to the boiling point of the solvent, preferably 10
The temperature is 0°C or higher.
反応終了後は水とベンゼン、トルエン、テトラヒドロフ
ラン、クロロホルムなどの有機溶媒を加えて目的物を分
取し、溶媒を留去することによって本発明化合物を得る
ことかできる。この方法による製造例を実施例1〜2に
示した。なお出発原料である(IV)式化合物は公知化
合物てあり、(V)式化合物は公知化合物または公知化
合(Chem、Ber、)第103巻、第2356頁〜
2367頁(1970年)に記載の製造法に準じ、対応
するカルボン酸ハライドとフェニルクリシンとの反応に
より容易に製造てきる。After the reaction is completed, the compound of the present invention can be obtained by adding water and an organic solvent such as benzene, toluene, tetrahydrofuran, chloroform, etc. to separate the desired product and distilling off the solvent. Examples of production by this method are shown in Examples 1 and 2. Note that the compound of formula (IV), which is a starting material, is a known compound, and the compound of formula (V) is a known compound or a compound of known compound (Chem, Ber), Vol. 103, p. 2356-
It can be easily produced by reacting the corresponding carboxylic acid halide with phenylchrysine according to the production method described on page 2367 (1970).
方法(B)
一般式(I)てR1か低級アルキル基、フェニル低級ア
ルキル基てR2か低級アルコキシの化合物(I ) ″
は方法(A)で得られた化合物(I)′と低級アルキル
ハライドあるいはフェニル低級アルキルハライドとを反
応させることにより製造てきる。Method (B) Compound (I) of general formula (I) where R1 is a lower alkyl group, phenyl lower alkyl group and R2 is lower alkoxy
can be produced by reacting the compound (I)' obtained in method (A) with a lower alkyl halide or a phenyl lower alkyl halide.
(I ) ′
(I ) ”
(式中、R4は前記に同してあり、Xはハロゲン原子を
示す6)
この反応は通常有機溶媒中て行う。使用てきる溶媒とし
ては、ヘンセン、トルエン、ヘキサンなとの炭化水素類
、エチルエーテル、ジオキサン、テトラヒドロフランな
どのエーテル類、酢酸メチル、酢酸エチルなとのエステ
ル類、アセトン、メチルイソフチルケトンなとのケトン
類、アセトニトリル、プロピオニトリルなとのニトリル
類、ジメチルホルムアミド、ジメチルスルホキシドなど
である。(I)'(I)'' (In the formula, R4 is the same as above, and X represents a halogen atom6) This reaction is usually carried out in an organic solvent. Examples of solvents that can be used include Hensen, toluene, Hydrocarbons such as hexane, ethers such as ethyl ether, dioxane, and tetrahydrofuran, esters such as methyl acetate and ethyl acetate, ketones such as acetone and methyl isophthyl ketone, acetonitrile, propionitrile, etc. Nitriles, dimethylformamide, dimethyl sulfoxide, etc.
酸結合剤としては、水素化ナトリウム、炭酸カリウムな
どの無機塩基、あるいはトリエチルアミン、とリシンな
との有機塩基か使用てきる。As acid binders, inorganic bases such as sodium hydride and potassium carbonate, or organic bases such as triethylamine and lysine can be used.
反応は室温ても進行するか、溶媒の沸点まての範囲て加
湿することにより、反応時間を短縮てきる。The reaction can proceed at room temperature, or the reaction time can be shortened by humidifying the solvent up to its boiling point.
反応終了後は水とヘンセン、トルエン、テトラヒドロフ
ランなどの有機溶媒を加えて目的物を分取し、溶媒を留
去することによって1本発明化合物を得ることかてきる
。方法(B)による製造例を実施例3〜4に示した。After the reaction is completed, water and an organic solvent such as Hensen, toluene, or tetrahydrofuran are added to separate the desired product, and the solvent is distilled off to obtain a compound of the present invention. Examples of production by method (B) are shown in Examples 3 and 4.
方】L工C>−
一般式(I)てR2かヒドロキシル基、低級アし)であ
る化合物CI ) ’は方法(A)あるいは方法(B)
により得た一般式(I)のR2か低級アルコキシである
化合物(1)′あるいは(I ) ″を加水分解するこ
と、さらに加水分解物を酸ハロゲン化物(■)した後、
低級アルキルメルカプタンあるいはアンモニア、低級ア
ルキルアミン、2,6−シエチルアニリンと反応させる
ことにより製造てきる。Method] Compound CI whose general formula (I) is R2, hydroxyl group, lower acetate) ' is method (A) or method (B)
After hydrolyzing the compound (1)' or (I)'' in which R2 of the general formula (I) obtained by is lower alkoxy, and further converting the hydrolyzate into an acid halide (■),
It can be produced by reacting with a lower alkyl mercaptan, ammonia, a lower alkylamine, or 2,6-ethylaniline.
■ あるいは 工 ■ )゛ 〔 ■ ″式中 R1 は前記に 同し、 は低級アルコキシ基を示す。■ or Engineering ■ )゛ [ ■ ″During the ceremony R1 is mentioned above Same, represents a lower alkoxy group.
〕 ■ )′ 式中、 R1 は前記に同じ。) (V) (I ) ’ (V)式中、 は前記に同し。] ■ )′ During the ceremony, R1 is the same as above. ) (V) (I)’ (V) In the formula, is the same as above.
〕
〔(1)″′式中、P−1,Rsは前記に同してあR6
は前記に同しである。)〕
この加水分解反応は通常有機溶媒中、水中あるいは水と
有機溶媒の混合溶媒中て酸あるいはアルカリを使用して
行う。使用てきる溶媒としてはアルコール類、エーテル
類、水なとかある。使用てきる酸としては、塩酸、硫酸
などの鉱酸類かあり、また使用てきるアルカリとしては
、水酸化ナトリウム、水酸化カリウムなとかある。] [(1)'' In the formula, P-1 and Rs are the same as above and R6
is the same as above. )] This hydrolysis reaction is usually carried out using an acid or an alkali in an organic solvent, water, or a mixed solvent of water and an organic solvent. Examples of solvents that can be used include alcohols, ethers, and water. Examples of acids that can be used include mineral acids such as hydrochloric acid and sulfuric acid, and examples of alkalis that can be used include sodium hydroxide and potassium hydroxide.
処理法としては酸を用いて加水分解した場合は反応後ベ
ンゼン、トルエン、クロロホルムなどの有機溶媒を加え
、適宜水洗して目的物を分取し、溶媒を留去する。また
アルカリを用いて加水分解した場合は、反応終了後、塩
酸なとの酸を加えて酸性とし、ベンゼン、トルエン、ク
ロロホルムなとの有機溶媒を加え、適宜水洗して目的物
を分取し、溶媒を留去する。上記の酸クロライド反応は
加水分解反応により得られる化合物(I ) ’のカル
ホキシル銹導体と塩化チオニルなととの反応により行い
得る。この反応に使用てきる溶媒としては、ベンセン、
トルエンなとの炭化水素類、クロロホルムなどのハロゲ
ン化炭化水素類なとがある。−数式(V)の酸ハロゲン
化物とアミン類あるいはチオール類とのアミド化反応あ
るいはチオエステル化反応は通常有機溶媒中て酸結合剤
を用いて行う。使用てきる溶媒としては、ベンセン、ト
ルエンなどの炭化水素類、クロロホルムなとのハロゲン
化炭化水素なとかある。As a treatment method, when hydrolysis is performed using an acid, an organic solvent such as benzene, toluene, or chloroform is added after the reaction, the target product is separated by washing with water as appropriate, and the solvent is distilled off. In addition, in the case of hydrolysis using an alkali, after the reaction is completed, add an acid such as hydrochloric acid to make it acidic, add an organic solvent such as benzene, toluene, or chloroform, wash with water as appropriate, and separate the target product. The solvent is distilled off. The above acid chloride reaction can be carried out by reacting a carboxyl salt conductor of compound (I)' obtained by a hydrolysis reaction with thionyl chloride. Solvents that can be used for this reaction include benzene,
These include hydrocarbons such as toluene and halogenated hydrocarbons such as chloroform. - The amidation reaction or thioesterification reaction between the acid halide of formula (V) and amines or thiols is usually carried out in an organic solvent using an acid binder. Examples of solvents that can be used include hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as chloroform.
酸結合剤としてはトリエチルアミン、ピリジンなとの有
機塩基か使用てきる。Organic bases such as triethylamine and pyridine can be used as acid binders.
方法(C)による製造例を実施例5〜6に示した。Examples of production by method (C) are shown in Examples 5 and 6.
アセチレンカルボン酸ジメチルエステル7 。Acetylene carboxylic acid dimethyl ester 7.
gとN−ニコチノイルフェニルクリシン8gおよび無水
酢酸 150m文の混合物を140°Cて1時間攪拌し
た。冷却後、無水酢酸を減圧下に留去し、トルエンと水
を加え、有機層を分取した。水洗後、減圧下にて溶媒を
留去すると標記化合物か褐色油状物として 10.0g
得られた。これをシリカケルカラムクロマトクラフィー
にて精製すると白色結晶となり、融点132−135℃
を示した。A mixture of 8 g of N-nicotinoylphenylchrysine and 150 m of acetic anhydride was stirred at 140°C for 1 hour. After cooling, acetic anhydride was distilled off under reduced pressure, toluene and water were added, and the organic layer was separated. After washing with water, the solvent was distilled off under reduced pressure to obtain 10.0 g of the title compound as a brown oil.
Obtained. When this is purified by silica gel column chromatography, it becomes white crystals with a melting point of 132-135℃.
showed that.
アセチレンジカルボン酸ジメチルエステル 71gとN
−)−リフルオロアセチルフェニルクリシン 12.4
gおよび無水酢酸 150m文の混合物を140°Cて
2時間攪拌した。冷却後、無水酢酸を減圧下に留去し、
トルエンと水を加え、有機層を分取した。水洗後、減圧
下に溶媒を留去すると標記化合物か褐色油状物として1
2.9g得られた。これをシリカケルクロマトクラフィ
ーにて精製すると無色油状物となり、
n、=1゜
186を示した。Acetylenedicarboxylic acid dimethyl ester 71g and N
-)-Lifluoroacetylphenylchrysin 12.4
A mixture of 150 ml of acetic anhydride and 150 ml of acetic anhydride was stirred at 140°C for 2 hours. After cooling, acetic anhydride was distilled off under reduced pressure.
Toluene and water were added, and the organic layer was separated. After washing with water, the solvent was distilled off under reduced pressure to obtain the title compound as a brown oil.
2.9g was obtained. When this was purified by silica gel chromatography, it became a colorless oil with n=1°186.
実施例1て得た2−(3−ピリジル)−5−フェニル−
3,4−ジカルボン酸ジメチルエステル(化合物ND2
)6.7gとペンシルクロライド2.6gをジメチルホ
ルムアミド 100rnJJに溶解し、水素化ナトリウ
ム 500 m gを加え80°Cにて2時間攪拌した
。冷却後、トルエンと水を加え、有機層を分取した。水
洗後、減圧にて溶媒を留去すると標記化合物か淡褐色油
状物として8.0g得られた。これをシリカゲルカラム
クロマトクラフィーにて精製すると白色結晶となり、融
点 104−106℃を示した。2-(3-pyridyl)-5-phenyl- obtained in Example 1
3,4-dicarboxylic acid dimethyl ester (compound ND2
) and 2.6 g of pencil chloride were dissolved in 100 rnJJ of dimethylformamide, 500 mg of sodium hydride was added, and the mixture was stirred at 80°C for 2 hours. After cooling, toluene and water were added, and the organic layer was separated. After washing with water, the solvent was distilled off under reduced pressure to obtain 8.0 g of the title compound as a pale brown oil. When this was purified by silica gel column chromatography, it became white crystals with a melting point of 104-106°C.
実施例41−メチル−2−(2−チエニル)方法(A)
により製造した2−(2−−F−エニル)−5−フェニ
ル−3,4−ジカルボン酸ジメチルエステル(化合物N
o1O)6.8gとヨウ化メチル 3.0gと炭酸カリ
3.0gおよびジメチルスルホキシド 100mJJ
の混合物を6゜0Cて3時間攪拌した。冷却後、木とト
ルエンを加え、有機層を分取した。水洗後、減圧にて溶
媒を留去すると標記化合物か淡褐色油状物として6゜5
g得られた。これをシリカケルカラムクロマトクラフィ
ーにて精製すると白色結晶となり、融点75−78℃を
示した。Example 4 1-Methyl-2-(2-thienyl) Method (A)
2-(2--F-enyl)-5-phenyl-3,4-dicarboxylic acid dimethyl ester (compound N
o1O) 6.8g, methyl iodide 3.0g, potassium carbonate 3.0g and dimethyl sulfoxide 100mJJ
The mixture was stirred at 6°0C for 3 hours. After cooling, wood and toluene were added, and the organic layer was separated. After washing with water, the solvent was distilled off under reduced pressure, and the title compound was obtained as a pale brown oil at 6°5.
g was obtained. When this was purified by silica gel column chromatography, it became white crystals with a melting point of 75-78°C.
実施例1て製造した2−(3−ピリジル)−5フェニル
−ビロール−3
4−ジカルボン酸シ
メチルエステル(化合物Nb2)6.7g、水酸化ナト
リウム 2.0g、エタノール 50mMと水 50m
文の混合物を70 ’Cて1時間攪拌した。冷却後、水
50 m fL、クロロホルム lo。6.7 g of 2-(3-pyridyl)-5phenyl-virol-3 4-dicarboxylic acid dimethyl ester (compound Nb2) prepared in Example 1, 2.0 g of sodium hydroxide, 50 mM of ethanol, and 50 m of water.
The mixture was stirred at 70'C for 1 hour. After cooling, add 50 m fL of water, lo of chloroform.
m文を加え、次いてl規定塩酸55m文て酸性とした。Then, the mixture was made acidic with 55 m of 1 normal hydrochloric acid.
クロロホルム層を分取し、減圧にて溶媒を留去すると標
記化合物か白色結晶として6.0g得られた。これをヘ
キサン、アセトン混合溶媒て再結晶すると、融点177
−180’Cを示した。The chloroform layer was separated and the solvent was distilled off under reduced pressure to obtain 6.0 g of the title compound as white crystals. When this is recrystallized from a mixed solvent of hexane and acetone, the melting point is 177.
-180'C was shown.
(C) 〕
実施例5て製造した2−(3−ピリジル)−5〜フェニ
ル−ピロール−3,5−ジカルボン酸(化合物No1)
6.2gと塩化チオニル8g、触媒量のピリジンおよび
ベンセン100mMの混合物を60〜70℃て1時間攪
拌した。冷却後、過剰の塩化チオニルとベンセンを減圧
下に留去した。この残液と2,6−シエチルアニリン
6゜0g、トリエチルアミン4.1g、クロロホルム1
00mMの混合物に氷水冷下3°Cにて滴下した。滴下
後、室温下て1時間撹拌した。この後、水100 m
lを加えてクロロホルム層を分取した。水洗後、減圧下
にて溶媒を留去すると標記化合物か淡黄色結晶として
11.og得られた。(C)] 2-(3-pyridyl)-5-phenyl-pyrrole-3,5-dicarboxylic acid produced in Example 5 (Compound No. 1)
A mixture of 6.2 g, 8 g of thionyl chloride, a catalytic amount of pyridine, and 100 mM of benzene was stirred at 60 to 70° C. for 1 hour. After cooling, excess thionyl chloride and benzene were distilled off under reduced pressure. This residual liquid and 2,6-ethylaniline
6゜0g, triethylamine 4.1g, chloroform 1
It was added dropwise to the 00mM mixture at 3°C while cooling with ice water. After the addition, the mixture was stirred at room temperature for 1 hour. After this, 100 m of water
1 was added and the chloroform layer was separated. After washing with water, the solvent is distilled off under reduced pressure to obtain the title compound as pale yellow crystals.
11. og obtained.
これをトルエン、アセトン混合溶媒て再結晶すると白色
結晶となり、融点230−234°Cを示した。When this was recrystallized from a mixed solvent of toluene and acetone, it became white crystals with a melting point of 230-234°C.
一虹害]虻カつ−除草剤の製剤化方法
節2の本発明の除草剤は、前記した一般式(I)の化合
物を慣用の処方により、乳剤、水和剤、液剤、フロアフ
ル(ゾル)剤、粉剤、トリフトレス(DL)粉剤、粒剤
、微粒剤、錠剤なとの適宜の形態として調製てきる。こ
こに使用される担体としては、農園共用薬剤に常用され
るものならば固体または液体のいずれても使用てき、特
定のものに限定されるものてはない。例えば、これら担
体としては、鉱eJ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
ーミキュライト、石膏、炭酸カルシウム、リン灰石、ホ
ワイトカーホン、消石灰珪砂、硫安、尿素など)、植物
質粉末(大豆粉、小麦粉、木粉、タバコ粉、デンプン、
結晶セルロースなと)、高分子化合物(石油樹脂、ポリ
塩化ビニル、ケトン樹脂、ダンツルヵムなと)、アルミ
ナ、ケイ酸塩、糖重合体、高分散性ケイ酸、ワックス類
などが挙げられる。また、液体担体としては、水、アル
コール類(メチルアルコールエチルアルコール、n−プ
ロピルアルコール l5O−プロピルアルコール、フタ
ノール、エチレンクリコール、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
、エチルヘンゼン、メチルナフタレンなど)、ハロゲン
化炭化水素類(クロロホルム、四塩化炭素ジクロルメタ
ン、クロルエチレン、モノクロルヘンゼン、トリクロル
フルオルメタン、ジクロルフルオルメタンなど)、エー
テル類(エチルエーテル、エチレンオキシド、ジオキサ
ン、テトラヒドロフランなと)、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、メチルイソメ
チルケトン、インホロンなと)、エステル類(酢酸エチ
ル、酢酸メチル、エチレンクリコールアセテート、酢酸
アミルなと)、酸アミド類(ジメチルホルムアミド、ジ
メチルアセトアミドなと)、ニトリル類(アセトニトリ
ル、プロピオニトリル、アクリロニトリルなど)、スル
ホキシド類(ジメチルスルホキシドなど)、アルコール
エーテル類(エチレンクリコールモノメチルエーテル、
エチレンクリコールモノエチルエーテルなと)、脂肪族
または脂環式炭化水素類(n−ヘキサン、シクロヘキサ
ンなと)、工業用ガソリン(石油エーテル、ソルベント
ナフサなと)、石油留分(パラフィン類、灯油、軽油な
と)などが挙げられる。The herbicide of the present invention described in Section 2 of Formulation Method of Herbicide can be prepared by adding the compound of general formula (I) to emulsions, wettable powders, liquids, floorfuls (sols), etc. ), powder, trifless (DL) powder, granules, fine granules, and tablets. As the carrier used herein, any solid or liquid carrier that is commonly used for agricultural common medicines may be used, and the carrier is not limited to a specific carrier. For example, these carriers include mineral powders (kaolin, bentonite,
Clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate, apatite, white carbon, slaked lime silica sand, ammonium sulfate, urea, etc.), vegetable powder (soybean flour, wheat flour, wood flour, tobacco flour, starch) ,
Examples include crystalline cellulose), polymer compounds (petroleum resin, polyvinyl chloride, ketone resin, Danzurcum), alumina, silicates, sugar polymers, highly dispersed silicic acid, and waxes. Liquid carriers include water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, l5O-propyl alcohol, phthanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xylene, ethyl alcohol, etc.). , methylnaphthalene, etc.), halogenated hydrocarbons (chloroform, carbon tetrachloride dichloromethane, chloroethylene, monochlorohensen, trichlorofluoromethane, dichlorofluoromethane, etc.), ethers (ethyl ether, ethylene oxide, dioxane, tetrahydrofuran, etc.) ), ketones (acetone,
Methyl ethyl ketone, cyclohexanone, methyl isomethyl ketone, inholon, etc.), esters (ethyl acetate, methyl acetate, ethylene glycol acetate, amyl acetate, etc.), acid amides (dimethylformamide, dimethylacetamide, etc.), nitriles ( acetonitrile, propionitrile, acrylonitrile, etc.), sulfoxides (dimethyl sulfoxide, etc.), alcohol ethers (ethylene glycol monomethyl ether,
(ethylene glycol monoethyl ether, etc.), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane, etc.), industrial gasoline (petroleum ether, solvent naphtha, etc.), petroleum distillates (paraffins, kerosene, etc.) , light oil), etc.
また、乳剤、水和剤、フロアツル剤なとの製剤に際して
、乳化、分散、可溶化、湿潤、発泡、潤滑、拡展なとの
目的て各種の界面活性剤(または乳化剤)か使用される
。このような界面活性剤としては、非イオン型(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
ルキルエステル、ポリオキシエチレンソルヒタンアルキ
ルエステルなと)、陰イオン型(アルキルベンゼンスル
ホネート、アルキルスルホサクシネート、アルキルサル
フェート、ポリオキシエチレンアルキルサルフェート、
アリールスルホネートなと)、陽イオン型(アルキルア
ミン類(ラウリルアミン、ステアリルトリメチルアンモ
ニウムクロライド、アルギルジメチルペンシルアンモニ
ウムクロライドなと)、ポリオキシエチレンアルキルア
ミン類)、両性型〔カルボン酸(ヘタイン型)、硫酸エ
ステル塩など〕などが挙けられるか、もちろんこれらの
例示のみに限定されるものてはない。In addition, various surfactants (or emulsifiers) are used for the purposes of emulsification, dispersion, solubilization, wetting, foaming, lubrication, and spreading when preparing emulsions, wettable powders, and flooring agents. Such surfactants include nonionic types (polyoxyethylene alkyl ethers, polyoxyethylene alkyl esters, polyoxyethylene solhitane alkyl esters, etc.) and anionic types (alkylbenzene sulfonates, alkyl sulfosuccinates, alkyl sulfates, etc.). , polyoxyethylene alkyl sulfate,
arylsulfonate), cationic type (alkylamines (laurylamine, stearyltrimethylammonium chloride, argyldimethylpentylammonium chloride), polyoxyethylene alkylamines), amphoteric type [carboxylic acid (hetaine type), sulfuric acid ester salts, etc.], but the present invention is not limited to these examples.
また、これらのほかにポリビニルアルコール(PVA)
、カルホキジメチルセルロース(CMC)、アラビアゴ
ム、ポリ上ニルアセテート1セラチン、アルキン酸ソー
タ、トラカカントゴムなとの各種補助剤を使用すること
かてきる。In addition to these, polyvinyl alcohol (PVA)
It is possible to use various adjuvants such as , carboxydimethylcellulose (CMC), gum arabic, polypyridyl acetate 1-seratin, alkinoic acid sorta, and gum tracacanth.
本発明においては、前記した各種製剤を製造するに際し
て、本発明化合物を0.001%〜95%(重量%:以
下同し)、好ましくは、0.01%〜90%の範囲て含
有するように製剤化することかてきる。例えば、通常、
粉剤、DL粉剤、微粉剤(F)の場合は、0.01%〜
5%1粒剤の場合は、0.01%〜10%、水和剤、乳
剤、液剤の場合は、1%〜75%の範囲て含有てきる。In the present invention, when producing the various preparations described above, the compound of the present invention is contained in a range of 0.001% to 95% (weight %: the same hereinafter), preferably 0.01% to 90%. It can be formulated into a formulation. For example, usually
For powders, DL powders, and fine powders (F), 0.01%~
In the case of 5% single granules, the content ranges from 0.01% to 10%, and in the case of wettable powders, emulsions, and liquids, the content ranges from 1% to 75%.
このように調製された製剤は、例えば、粒剤の場合は、
そのまま土壌表面、土壌中または水中に活性成分量とし
てlOアール当り0.3g〜300g程度の範囲て散布
すればよい。水和剤、乳剤およびツル剤などの場合は、
水または適当な溶剤に希釈し、活性成分量として10ア
ール当り0.3〜300g程度の範囲て散布すればよい
。For example, in the case of a granule, the preparation prepared in this way is
The active ingredient may be sprayed directly on the soil surface, in the soil, or in water in an amount of about 0.3 to 300 g per 10 are. For wettable powders, emulsions and vines,
It may be diluted with water or a suitable solvent and sprayed in an amount of about 0.3 to 300 g of active ingredient per 10 ares.
また本発明化合物を除草剤として使用するに際して、既
知の除草剤、殺虫剤あるいは植物調節剤などと混用して
適用性の拡大を図ることかてきまた場合によっては、相
乗効果を期待することもてきる。Furthermore, when using the compound of the present invention as a herbicide, it may be possible to expand its applicability by mixing it with known herbicides, insecticides, or plant regulators, and in some cases, it may be possible to expect a synergistic effect. Ru.
前記した一般式(I)の本発明化合物を除草剤として製
剤化する方法について以下の実施例7〜lOをもって説
明する。たたし1本発明はこれらの実施例に限定される
ものてはなく、他の種々の添加物と任意の割合て混合て
き、また前述のような他の除草剤などを任意の割合て混
合し製剤化することもてきる。A method for formulating the compound of the present invention of general formula (I) as a herbicide will be explained with reference to Examples 7 to 1O below. However, the present invention is not limited to these examples, and may be mixed with various other additives in any proportion, and other herbicides as described above may be mixed in any proportion. It can also be made into a formulation.
なお、化合物陥は、前記の第1表に示したものてあり、
また実施例中て部とは、すべて重量部を示す。In addition, the compound defects are shown in Table 1 above,
Furthermore, all parts in the examples refer to parts by weight.
実施例7(粒剤)
化合物Nolの化合Th1部、ラウリルサルフェート
1部、リクニンスルホン酸カルシウム1部、ベントナイ
ト 30部および白土 67部に水 15部を加えて混
線機て混線した後、造粒機て造粒し、流動乾燥機て乾燥
して、活性成分1%を含む粒剤を得る。Example 7 (granules) 1 part of compound Th of compound Nol, lauryl sulfate
1 part of calcium ricnin sulfonate, 30 parts of bentonite, and 67 parts of white clay were mixed with 15 parts of water, mixed in a mixer, granulated in a granulator, and dried in a fluidized dryer to obtain the active ingredient. Granules containing 1% are obtained.
実施例8(水利剤)
化合物No2の化合物 15部、ホワイトカーホン 1
5部、リクニンスルホン酸カルシウム3部、ポリオキシ
エチレンノニルフェニルエーテル2部、珪藻± 5部お
よびクレー 60部を粉砕混合機て均一に混合して、活
性成分15%を含む水和剤を得る。Example 8 (Irrigation agent) Compound No. 2 compound 15 parts, white carphone 1
5 parts of calcium likunin sulfonate, 3 parts of polyoxyethylene nonyl phenyl ether, 5 parts of diatom and 60 parts of clay are uniformly mixed in a grinding mixer to obtain a wettable powder containing 15% of the active ingredient. .
施例9(乳剤)
化合物No19の化合物 20部、ツルポール700H
(東邦化学工業株式会社製乳化剤)20部、およびキシ
レン 60部を混合して、活性成分20%を含む乳剤を
得る。Example 9 (emulsion) 20 parts of compound No. 19, Tsurupol 700H
(Emulsifier manufactured by Toho Chemical Industry Co., Ltd.) 20 parts and xylene 60 parts are mixed to obtain an emulsion containing 20% of the active ingredient.
実施例10(粉剤)
化合物Nb26の化合物 0.5部、無水珪酸微粉末
0.5部、ステアリン酸カルシウム 0゜5部、クレー
50部およびタルク 48.5部を均一に混合粉砕し
て、活性成分0.5%を含む粉剤を得る。Example 10 (powder) Compound Nb26 0.5 part, silicic anhydride fine powder
0.5 parts of calcium stearate, 0.5 parts of calcium stearate, 50 parts of clay and 48.5 parts of talc are uniformly mixed and ground to obtain a powder containing 0.5% of the active ingredient.
発明の効果
一般式(I)の本発明化合物は、既知の類似化合物に比
較し、優れた除草活性と安全性を有する。Effects of the Invention The compound of the present invention represented by general formula (I) has superior herbicidal activity and safety compared to known similar compounds.
すなわち、本発明化合物は、ヒエ、ホタルイ、ヘラオモ
タカ、コナキ、アゼナ、キカシクサなどの水田雑草に対
して輻広く作用して、−これらの雑草に対して10アー
ル当り活性成分として、50gの施用量の処理て多くの
雑草をほぼ完全に除草することかてきる。また、メヒシ
バ、エノコログサ、シロザ、イヌビニ、イヌタデなどの
各種の畑地雑草に対しても、lOアール当り活性成分と
して100gの施用量の処理てほぼ完全に除草すること
かてきる。しかも水稲、クイズ、トウモロコシ、ヒート
、ナタネ、コムギなどの有用作物には薬害を与えない。That is, the compound of the present invention acts extensively on paddy field weeds such as barnyard grass, firefly, grasshopper, konaki, azalea, and kikashikusa. Many weeds can be almost completely eradicated by treatment. In addition, it is possible to almost completely eliminate various upland weeds such as crabgrass, foxtail grass, whiteweed, dogweed, and knotweed by applying 100 g of the active ingredient per 10 are. Moreover, it does not cause any chemical damage to useful crops such as paddy rice, corn, corn, heat, rapeseed, and wheat.
その上、人畜毒性や魚毒性もない。したかって、安全に
使用てきる。Furthermore, it is not toxic to humans or fish. It's safe to use if you want.
−数式(I)の本発明化合物の除草活性を例証するため
に試験例1乃至2を示す。- Test Examples 1 and 2 are shown to illustrate the herbicidal activity of the compound of the present invention represented by formula (I).
175000アールの大きさのワクネルポットに水田土
壌(沖積壌土)をつめ、その表層部にヒエ ホタルイ、
ヘラオモタカ、コナキ、アセナおよびキカシグサの種子
を各50粒ずつ均一に播種した。播種1日後に湛水し、
水深を2cmに保つた。播種3日後に水稲の2.5葉期
苗を1株2本植えてポット当り3株移植した。水稲移植
1日後に実施例9に準して調製した乳剤を水て希釈しポ
ット当りlOmjL(活性成分の使用量換算てlOアー
ル当り50g相当)を滴下した。A Wachner pot with a size of 175,000 are is filled with paddy soil (alluvial loam), and the surface layer is filled with barnyard grass, firefly,
Fifty seeds each of Helaomotaka, Konaki, Asena, and Kikashigusa were uniformly sown. Flooded one day after sowing,
The water depth was kept at 2 cm. Three days after sowing, two 2.5-leaf stage seedlings of paddy rice were planted, and three plants were transplanted per pot. One day after transplanting paddy rice, an emulsion prepared according to Example 9 was diluted with water, and 10mjL per pot (equivalent to 50 g per 1OmjL in terms of the amount of active ingredient used) was added dropwise.
本試験はl薬液濃度区当り2連制て行い、薬剤処理30
日後に以下に示す評価の指標に基づいて、除草効果およ
び水稲の薬害程度を調査した。This test was conducted in duplicate per 1 drug solution concentration section, and the drug treatment
After a day, the herbicidal effect and the degree of phytotoxicity of paddy rice were investigated based on the evaluation index shown below.
その結果は第2表のとおりである。The results are shown in Table 2.
除草率(%)
100%
80〜lOO%未満
60〜801ノ
40〜60I1
20〜401ノ
20ノl
薬害の評価値
薬害程度
枯 死
薬害大
Iノ中
lノ小
ツノ僅小
Is
第
表
(イギリス特許第2194788号公報記載の化合e5
>(−膜化・フタクロール)
試験例2 畑作雑草に対する除草効果および作物1)雑
草に対する除草効果試験
115000アールの大きさの素焼製ポットに畑土壌(
沖積壌土)をつめ、表層1cmの土壌とメヒシバ、エノ
コログサ、シロザ、イヌヒュ、イヌタデの各種雑草種子
それぞれ50粒を均一に混合し1表層を軽く押圧した。Weeding rate (%) 100% Less than 80-1OO% 60-801, 40-60I1 20-401, 20Nl Evaluation value of drug damage Degree of drug damage Blight Plant damage Major I Medium Small horn Slight Is Table (UK) Compound e5 described in Patent No. 2194788
>(-Film formation/Futachlor) Test Example 2 Herbicidal effect on field weeds and crops 1) Test of herbicidal effect on weeds Field soil (
Alluvial loam) was packed, and 50 seeds each of various weeds such as crabgrass, foxtail grass, whiteweed, Japanese knotweed, and Japanese knotweed were evenly mixed with the soil in the surface layer of 1 cm, and one surface layer was lightly pressed.
播種2日後に実施例9に準して調製した乳剤を水て希釈
し、lOアール当り1001の処理薬剤(活性成分の施
用量換算てlOアール当り100g相当)を土壌表面に
OJi霧して処理した。Two days after sowing, the emulsion prepared according to Example 9 was diluted with water, and 1001 treatment chemicals per 10 are (equivalent to 100 g per 10 are in terms of application amount of active ingredient) were sprayed onto the soil surface. did.
本試験はl薬液濃度区当り2連制て行い、薬剤処理30
日後に除草効果を試験例1と同様の評価の指標に基づい
て調査した。This test was conducted in duplicate per 1 drug solution concentration section, and the drug treatment
Days later, the herbicidal effect was investigated based on the same evaluation index as in Test Example 1.
2)作物に対する薬害試験
1/10,000アールの素焼製ポットに畑土壌(沖積
壌土)をつめ、各作物の種子(ダイス5粒、トウモロコ
シ5粒、ビート10粒、ナタネ10粒およびコムギ10
粒をそれぞれ別のポットに播種し、表層を軽く押圧した
。播種1日後に実施例9に準して調製した乳剤を水て希
釈し、10アール当り100又の処理薬剤(活性成分量
てlOアール当り100g相当)を土壌表面に噴霧した
。2) Test for phytotoxicity on crops Fill field soil (alluvial loam) in 1/10,000 are clay pots, and add seeds of each crop (5 dice, 5 corn, 10 beets, 10 rapeseed, and 10 wheat).
The grains were sown in separate pots, and the surface layer was lightly pressed. One day after sowing, an emulsion prepared according to Example 9 was diluted with water, and a treatment agent of 100 per 10 are (active ingredient amount equivalent to 100 g per 10 are) was sprayed onto the soil surface.
本試験はl薬液濃度区当り2連制て行い、薬剤処理30
日後に各作物に対する薬害程度を、試験例1と同様の評
価の指標に基づいて調査した。その結果は第3表のとお
りである。This test was conducted in duplicate per 1 drug solution concentration section, and the drug treatment
Days later, the degree of chemical damage to each crop was investigated based on the same evaluation index as in Test Example 1. The results are shown in Table 3.
Claims (1)
低級アルキル基を示し、R_2はヒドロキシル基、低級
アルコキシ基、低級アルキルチオ基、▲数式、化学式、
表等があります▼(式中、R_4、R_5は同一または
相異なってもよい水素原子、低級アルキル基、2,6−
ジエチルフェニル基を示す。)を示し、R_3はピリジ
ル基、チエニル基、フリル基、トリフルオロメチル基を
示す。)で表わされるピロールジカルボン酸誘導体。 2)一般式 ▲数式、化学式、表等があります▼ 〔式中、R_1は水素原子、低級アルキル基、フェニル
低級アルキル基を示し、R_2はヒドロキシル基、低級
アルコキシ基、低級アルキルチオ基、▲数式、化学式、
表等があります▼(式中、R_4、R_5は同一または
相異なってもよい水素原子、低級アルキル基、2,6−
ジエチルフェニル基を示す。)を示し、R_3はピリジ
ル基、チエニル基、フリル基、トリフルオロメチル基を
示す。〕で表わされるピロールジカルボン酸誘導体を活
性成分として含有することを特徴とする除草剤。[Claims] 1) General formula ▲ Numerical formula, chemical formula, table, etc. Alkylthio group, ▲mathematical formula, chemical formula,
There are tables, etc. ▼ (In the formula, R_4 and R_5 may be the same or different hydrogen atoms, lower alkyl groups, 2,6-
Indicates diethylphenyl group. ), and R_3 represents a pyridyl group, thienyl group, furyl group, or trifluoromethyl group. ) A pyrrole dicarboxylic acid derivative represented by 2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_1 represents a hydrogen atom, lower alkyl group, phenyl lower alkyl group, R_2 represents a hydroxyl group, lower alkoxy group, lower alkylthio group, ▲ Numerical formula, Chemical formula,
There are tables, etc. ▼ (In the formula, R_4 and R_5 may be the same or different hydrogen atoms, lower alkyl groups, 2,6-
Indicates diethylphenyl group. ), and R_3 represents a pyridyl group, thienyl group, furyl group, or trifluoromethyl group. ] A herbicide characterized by containing a pyrrole dicarboxylic acid derivative represented by the following as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26523290A JPH04145078A (en) | 1990-10-04 | 1990-10-04 | Pyrroledicarboxylic acid derivative and herbicide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26523290A JPH04145078A (en) | 1990-10-04 | 1990-10-04 | Pyrroledicarboxylic acid derivative and herbicide |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04145078A true JPH04145078A (en) | 1992-05-19 |
Family
ID=17414357
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP26523290A Pending JPH04145078A (en) | 1990-10-04 | 1990-10-04 | Pyrroledicarboxylic acid derivative and herbicide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04145078A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996017841A1 (en) * | 1994-12-06 | 1996-06-13 | Nippon Soda Co., Ltd. | Pyridylpyrrole compounds, process for production, and agrohorticultural bactericide |
JP2008508308A (en) * | 2004-07-30 | 2008-03-21 | エグゼリクシス, インコーポレイテッド | Pyrrole derivatives as pharmaceutical agents |
IT201800003680A1 (en) * | 2018-03-16 | 2019-09-16 | Univ Degli Studi Di Siena | ANTIVIRAL COMPOUNDS AND USES OF THEM |
-
1990
- 1990-10-04 JP JP26523290A patent/JPH04145078A/en active Pending
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996017841A1 (en) * | 1994-12-06 | 1996-06-13 | Nippon Soda Co., Ltd. | Pyridylpyrrole compounds, process for production, and agrohorticultural bactericide |
JP2008508308A (en) * | 2004-07-30 | 2008-03-21 | エグゼリクシス, インコーポレイテッド | Pyrrole derivatives as pharmaceutical agents |
JP2010077166A (en) * | 2004-07-30 | 2010-04-08 | Exelixis Inc | Pyrrole derivative as pharmaceutical factor |
US8026237B2 (en) | 2004-07-30 | 2011-09-27 | Exelixis, Inc. | Pyrrole derivatives as pharmaceutical agents |
US8367667B2 (en) | 2004-07-30 | 2013-02-05 | Exelixis, Inc. | Pyrrole derivatives as pharmaceutical agents |
IT201800003680A1 (en) * | 2018-03-16 | 2019-09-16 | Univ Degli Studi Di Siena | ANTIVIRAL COMPOUNDS AND USES OF THEM |
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