JP2738010B2 - Pyrazole inducers and selective herbicides - Google Patents
Pyrazole inducers and selective herbicidesInfo
- Publication number
- JP2738010B2 JP2738010B2 JP1120983A JP12098389A JP2738010B2 JP 2738010 B2 JP2738010 B2 JP 2738010B2 JP 1120983 A JP1120983 A JP 1120983A JP 12098389 A JP12098389 A JP 12098389A JP 2738010 B2 JP2738010 B2 JP 2738010B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- och
- carbon atoms
- ome
- same meaning
- 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 - Fee Related
Links
- 239000004009 herbicide Substances 0.000 title claims description 19
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title claims description 3
- 239000000411 inducer Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 134
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 36
- 230000002363 herbicidal effect Effects 0.000 claims description 32
- -1 cyanomethyl group Chemical group 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 229910004013 NO 2 Inorganic materials 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 6
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- 150000003217 pyrazoles Chemical class 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 2
- 229960001231 choline Drugs 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 2
- 229910052777 Praseodymium Inorganic materials 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002689 soil Substances 0.000 description 14
- 238000009472 formulation Methods 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- 238000005507 spraying Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- 235000005822 corn Nutrition 0.000 description 8
- 239000002841 Lewis acid Substances 0.000 description 7
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- 230000009969 flowable effect Effects 0.000 description 7
- 150000007517 lewis acids Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000002736 nonionic surfactant Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 5
- NPRXQXFTKCBAAY-UHFFFAOYSA-N 4-benzoylpyrazole Chemical class C=1C=CC=CC=1C(=O)C=1C=NNC=1 NPRXQXFTKCBAAY-UHFFFAOYSA-N 0.000 description 5
- CKVRMLXDWKZMOW-UHFFFAOYSA-N CCN1N=CC(C(=O)C=2C(=C(OCC=3C=CC=CC=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O Chemical compound CCN1N=CC(C(=O)C=2C(=C(OCC=3C=CC=CC=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O CKVRMLXDWKZMOW-UHFFFAOYSA-N 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- 240000006394 Sorghum bicolor Species 0.000 description 5
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
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- 238000009835 boiling Methods 0.000 description 5
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- 239000004563 wettable powder Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- XPNHHPXSCYDOKL-UHFFFAOYSA-N 4-benzoyl-1,2-dihydropyrazol-3-one Chemical class N1N=CC(C(=O)C=2C=CC=CC=2)=C1O XPNHHPXSCYDOKL-UHFFFAOYSA-N 0.000 description 4
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- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
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- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 3
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- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
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- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- 238000006482 condensation reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- WVANEDDSWQMDIK-UHFFFAOYSA-N 2-chloro-3-(2-methoxyethoxy)-4-methylsulfonylbenzoic acid Chemical compound COCCOC1=C(Cl)C(C(O)=O)=CC=C1S(C)(=O)=O WVANEDDSWQMDIK-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000005494 Chlorotoluron Substances 0.000 description 1
- 239000005496 Chlorsulfuron Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000005853 Cyperus esculentus Nutrition 0.000 description 1
- 244000075634 Cyperus rotundus Species 0.000 description 1
- 239000005504 Dicamba Substances 0.000 description 1
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
- 239000005507 Diflufenican Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001596950 Larimichthys crocea Species 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- IBZHOAONZVJLOB-UHFFFAOYSA-N Tridiphane Chemical compound ClC1=CC(Cl)=CC(C2(CC(Cl)(Cl)Cl)OC2)=C1 IBZHOAONZVJLOB-UHFFFAOYSA-N 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 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
- 230000000386 athletic effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical class N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 1
- NTIYZHVRDWFFLS-UHFFFAOYSA-N benzyl 2-chloro-4-methylsulfonyl-3-phenylmethoxybenzoate Chemical compound ClC1=C(OCC=2C=CC=CC=2)C(S(=O)(=O)C)=CC=C1C(=O)OCC1=CC=CC=C1 NTIYZHVRDWFFLS-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-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
- 150000007527 lewis bases Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical group CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 1
- DJUMDLDURBDBJJ-UHFFFAOYSA-N methyl 3-bromo-5-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-1-methylpyrazole-4-carboxylate Chemical compound BrC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC DJUMDLDURBDBJJ-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は新規な４−ベンゾイルピラゾール誘導体およ
び該誘導体を有効成分として含有する選択性除草剤に関
するものであり、特に畑地用除草剤として有用である。Description: TECHNICAL FIELD The present invention relates to a novel 4-benzoylpyrazole derivative and a selective herbicide containing the derivative as an active ingredient, and is particularly useful as a herbicide for upland fields. is there.
従来、長年にわたる除草剤の研究開発の中から多種多
様な薬剤が実用化され、これら除草剤は雑草防除作業の
省力化や農園芸作物の生産性向上に寄与してきた。Conventionally, a wide variety of chemicals have been put into practical use from many years of research and development of herbicides, and these herbicides have contributed to labor saving of weed control work and improvement of productivity of agricultural and horticultural crops.
今日においても、より卓越した除草特性を有する新規
薬剤の開発が要望され、特に農園芸用除草剤としては栽
培作物に薬害を及ぼすことなく対象雑草のみを選択的に
かつ低薬量で防除し得ることが望ましいが、既存の薬剤
は必ずしも好適な除草特性を有するものではない。Even today, there is a demand for the development of a new drug having more excellent herbicidal properties. In particular, as an agricultural and horticultural herbicide, it is possible to control only the target weed selectively and at a low dose without damaging the cultivated crop. Desirably, existing agents do not necessarily have favorable herbicidal properties.
一方、４−ベンゾイルピラゾール誘導体の特定の化合
物が除草活性を有することは、すでに公知であり、例え
ば、ピラゾレート（一般名）およびピラゾキシフェン
（一般名）は、水田用除草剤として実用化されている。
しかし、これらの化合物は水田用除草剤としては、優れ
た除草活性を有するが、畑地の雑草に対しては、その活
性が弱く、畑作用除草剤としては、適当なものではな
い。４−ベンゾイルピラゾール誘導体の中で、畑作用除
草剤として、さらに優れた化合物が要望されている。On the other hand, it is already known that a specific compound of a 4-benzoylpyrazole derivative has herbicidal activity. For example, pyrazolate (common name) and pyrazoxifen (common name) have been put to practical use as paddy herbicides.
However, these compounds have excellent herbicidal activity as a paddy field herbicide, but have weak activity against weeds in the field, and are not suitable as field-acting herbicides. Among the 4-benzoylpyrazole derivatives, more excellent compounds have been demanded as field-acting herbicides.
本発明は、 〔式中、Ａは炭素原子数１〜３のアルキル基、炭素原
子数２〜４のアルケニル基または炭素原子数２〜４のア
ルキニル基を表す。The present invention [In the formula, A represents an alkyl group having 1 to 3 carbon atoms, an alkenyl group having 2 to 4 carbon atoms or an alkynyl group having 2 to 4 carbon atoms.
Ｂは水素原子、炭素原子数１〜３のアルキル基、ハロ
ゲン原子、炭素原子数１〜３のハロアルキル基、炭素原
子数１〜３のアルコキシ基、炭素原子数１〜３のアルキ
ルチオ基、炭素原子数２〜４のアルコキシアルキル基、
炭素原子数２〜４のアルキルチオアルキル基または炭素
原子数２〜４のアルコキシカルボニル基を表す。B is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a halogen atom, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, an alkylthio group having 1 to 3 carbon atoms, a carbon atom An alkoxyalkyl group of Formulas 2 to 4,
Represents an alkylthioalkyl group having 2 to 4 carbon atoms or an alkoxycarbonyl group having 2 to 4 carbon atoms.
Ｘは炭素原子数１〜６のアルキル基、炭素原子数１〜
６のアルコキシ基、ハロゲン原子、ニトロ基、シアノ
基、炭素原子数１〜６のハロアルキル基、炭素原子数２
〜６のアルコキシアルキル基、炭素原子数２〜６のアル
キルカルボニル基、炭素原子数２〜６のアルコキシカル
ボニル基、互いに独立して水素または炭素原子数１〜６
のアルキル基により置換れているアミノカルボニル基、
炭素原子数１〜６のハロアルコキシ基、炭素原子数１〜
６のアルキルチオ基または炭素原子数２〜６のアルキル
チオアルキル基を表す。X is an alkyl group having 1 to 6 carbon atoms,
6 alkoxy groups, halogen atoms, nitro groups, cyano groups, haloalkyl groups having 1 to 6 carbon atoms, 2 carbon atoms
-C6 alkoxyalkyl group, C2-C6 alkylcarbonyl group, C2-C6 alkoxycarbonyl group, independently of each other hydrogen or C1-C6
An aminocarbonyl group substituted by an alkyl group of
Haloalkoxy group having 1 to 6 carbon atoms, 1 to 6 carbon atoms
6 represents an alkylthio group or an alkylthioalkyl group having 2 to 6 carbon atoms.
ＹはOR1基〔但し、R1は炭素原子数３〜８のシクロア
ルキル基、炭素原子数４〜８のシクロアルキルアルキル
基、炭素原子数３〜６のアルケニル基、炭素原子数２〜
６のアルキニル基、炭素原子数１〜６のハロアルキル
基、炭素原子数３〜８のハロシクロアルキルアルキル
基、炭素原子数３〜６のハロアルケニル基、炭素原子数
２〜６のハロアルキニル基、炭素原子数２〜６のニトロ
アルキル基または、炭素原子数１〜３のアルキル基、ハ
ロゲン原子、ニトロ基もしくは炭素原子数１〜３のアル
コキシ基により置換されていてもよいフェニル基を表
す。〕、 Ｏ−Ｌ−Ｏ−R1基〔但し、Ｌは炭素原子数１〜３のアル
キル基で置換されていてもよい炭素原子数１〜６のアル
キル基を表し、R1は前記と同様の意味を表す。〕、 Ｏ−Ｌ−OH基〔但し、Ｌは前記と同様の意味を表
す。〕、 Ｏ−Ｌ−Ｏ−Ｌ−Ｏ−R2基〔但し、Ｌは前記と同様の意
味を表し、R2は水素原子、炭素原子数１〜６のアルキル
基または、炭素原子数１〜３のアルキル基、ハロゲン原
子、ニトロ基もしくは炭素原子数１〜３のアルコキシ基
により置換されていてもよいフェニル基を表す。〕、 Ｏ−Ｌ−R3基〔但し、Ｌは前記と同様の意味を表す。R3
は炭素原子１〜３のアルキル基、ハロゲン原子、ニトロ
基もしくは炭素原子数１〜３のアルコキシ基により置換
されていてもよいフェニル基を表す。〕、 Ｏ−Ｍ基〔但し、Ｍは２個以内のイオウ原子あるいは酸
素原子を含み１〜４個の炭素原子と結合することによっ
て形成される員数３〜６の脂環式残基を表す。〕、 Ｏ−Ｌ−Ｍ基〔但し、ＬおよびＭは前記と同様の意味を
表す。〕、 Ｏ−Ｌ−NR4R5〔但し、Ｌは前記と同様の意味を表す。R
4およびR5は互いに独立して水素原子または炭素原子数
１〜６のアルキル基を表す。R4とR5は環を形成してもよ
い。〕、 Ｏ−Ｌ−COOR4基〔但し、ＬおよびR4は前記と同様の意
味を表す。〕、 Ｏ−CH＝CH-COOR4基〔但し、R4は前記と同様の意味を表
す。〕、 Ｏ−Ｌ−CN基〔但し、Ｌは前記と同様の意味を表
す。〕、 Ｏ−Ｌ−Ｃ（Ｏ）−R2基〔但し、ＬおよびR2は前記と同
様の意味を表す。〕、 Ｏ−Ｌ−S(O)n-R4基〔但し、ＬおよびR4は前記と同様の
意味を表す。ｎは０〜２の整数を表す。〕、 Ｏ−COOR4基〔但し、R4は前記と同様の意味を表
す。〕、 Ｏ−CONR4R5基〔但し、R4およびR5は前記と同様の意味
を表す。〕、 OP(O)(OR4)2基〔但し、R4は前記と同様の意味を表
す。〕、 S(O)nR1基〔但し、R1およびｎは前記と同様の意味を表
す。〕または S(O)n−Ｌ−Ｏ−R1基〔但し、Ｌ、R1およびｎは前記と
同様の意味を表す。〕を表す。Y is an OR 1 group, provided that R 1 is a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkylalkyl group having 4 to 8 carbon atoms, an alkenyl group having 3 to 6 carbon atoms,
6 alkynyl groups, haloalkyl groups having 1 to 6 carbon atoms, halocycloalkylalkyl groups having 3 to 8 carbon atoms, haloalkenyl groups having 3 to 6 carbon atoms, haloalkynyl groups having 2 to 6 carbon atoms, Represents a nitroalkyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 3 carbon atoms, a halogen atom, a nitro group, or a phenyl group which may be substituted by an alkoxy group having 1 to 3 carbon atoms. ], O-O-R 1 group [where L represents an alkyl group having 1 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 3 carbon atoms, and R 1 is the same as defined above. Represents the meaning of ], An O-L-OH group wherein L represents the same meaning as described above. ], O-OLOLOR 2 group [where L represents the same meaning as described above, and R 2 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a 1 to 2 carbon atoms. 3 represents a phenyl group which may be substituted by an alkyl group, a halogen atom, a nitro group or an alkoxy group having 1 to 3 carbon atoms. ], O-L-R 3 groups, wherein L represents the same meaning as described above. R 3
Represents a phenyl group which may be substituted by an alkyl group having 1 to 3 carbon atoms, a halogen atom, a nitro group or an alkoxy group having 1 to 3 carbon atoms. ], An O-M group [where M represents an alicyclic residue having 3 to 6 members formed by bonding to 1 to 4 carbon atoms containing up to 2 sulfur atoms or oxygen atoms. ], An OLM group [where L and M represent the same meaning as described above.] ], O-L-NR 4 R 5 [where, L is the same meanings as defined above. R
4 and R 5 independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 4 and R 5 may form a ring. ], An OL-COOR 4 group [where L and R 4 represent the same meaning as described above.] ], O-CH = CH-COOR 4 group [where R 4 represents the same meaning as described above.] ], An O-L-CN group wherein L represents the same meaning as described above. ], O-L-C (O ) -R 2 group [where, L and R 2 have the same meanings as defined above. ], O-LS (O) n -R 4 group [where L and R 4 represent the same meaning as described above.] n represents the integer of 0-2. ], O-COOR 4 group [where R 4 represents the same meaning as described above.] ], O-CONR 4 R 5 group [where, R 4 and R 5 have the same meanings as defined above. ], OP (O) (OR 4 ) 2 groups, provided that R 4 has the same meaning as described above. ], S (O) n R 1 group [where R 1 and n represent the same meaning as described above.] ] Or S (O) n -L—O—R 1 group, wherein L, R 1 and n represent the same meaning as described above. ].
Ｚはハロゲン原子、ニトロ基、炭素原子数１〜３のア
ルコキシ基、トリフルオロメチル基、トリフルオロメト
キシ基、シアノ基またはS(O)nR6基〔但し、ｎは前記と
同様の意味を表す。R6は炭素原子数１〜３のアルキル基
または炭素原子数１〜３のハロアルキル基を表す。〕を
表す。Z is a halogen atom, a nitro group, an alkoxy group having 1 to 3 carbon atoms, a trifluoromethyl group, a trifluoromethoxy group, a cyano group or an S (O) n R 6 group (where n has the same meaning as described above) Represent. R 6 represents an alkyl group having 1 to 3 carbon atoms or a haloalkyl group having 1 to 3 carbon atoms. ].
Ｖは水素原子、ハロゲン原子、炭素原子数１〜４のア
ルキル基または炭素原子数１〜４のアルコキシ基を表
す。V represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
Ｗは水素原子、ハロゲン原子、炭素原子数１〜４のア
ルキル基、炭素原子数１〜４のハロアルキル基、炭素原
子数１〜４のアルコキシ基、炭素原子数２〜６のアルコ
キシアルキル基、炭素原子数２〜５のアルコキシカルボ
ニル基、炭素原子数１〜３のハロアルコキシ基、ニトロ
基、シアノ基またはS(O)n-R6基〔但し、ｎおよびR6は前
記と同様の意味を表す。〕を表す。W represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, An alkoxycarbonyl group having 2 to 5 atoms, a haloalkoxy group having 1 to 3 carbon atoms, a nitro group, a cyano group or an S (O) n -R 6 group (where n and R 6 have the same meanings as described above) Represent. ].
Ｑは水素原子、ハロゲン原子で置換されていてもよい
炭素原子数１〜６のアルキル基、ハロゲン原子で置換さ
れていてもよい炭素原子数１〜６のアルケニル基、ハロ
ゲン原子で置換されていてもよい炭素原子数１〜６のア
ルキニル基、シアノメチル基、 −Ｃ（Ｏ）−R7基〔但し、R7は炭素原子数１〜６のアル
キル基、炭素原子数１〜６のアルケニル基、炭素原子数
１〜６のアルキニル基、炭素原子数１〜６のハロアルキ
ル基、炭素原子数１〜６のハロアルケニル基、炭素原子
数１〜６のハロアルキニル基、ハロゲン原子、ニトロ基
もしくはトルフルオロメチル基から選ばれた同一もしく
は相異なる置換基で置換されていてもよいフェニル基、
炭素原子数１〜６のアルキル基、炭素原子数１〜６のア
ルコキシ基または水酸基を表す。〕、 −S(O)2R7基〔但し、R7は前記と同様の意味を表
す。〕、 −P(O)(OR7)2基〔但し、R7は前記と同様の意味を表
す。〕、 −Ｌ−Ｃ（Ｏ）−R7基〔但し、ＬおよびR7は前記と同様
の意味を表す。〕 −Ｌ−Ｃ（Ｏ）−Ｎ（R8）（R9）基〔但し、Ｌは前記と
同様の意味を表す。R8およびR9は互いに独立して水素原
子または炭素原子数１〜６のアルキル基を表す。〕 −Ｌ−R10基〔但し、Ｌは前記と同様の意味を表す。〕 R10はハロゲン原子、ニトロ基もしくはトリフルオロ
メチル基から選ばれた同一もしくは相異なる置換基で置
換されていてもよいフェニル基、炭素原子数１〜６のア
ルキル基、炭素原子数１〜６のアルコキシ基または水酸
基を表す。〕、 −Ｌ−Ｎ（R8）（R9）基〔但し、Ｌ、R8およびR9は前記
と同様の意味を表す。〕、 −Ｌ−OR11基〔但し、Ｌは前記と同様の意味を表し、R
11は水素原子、炭素原子数１〜６のアルキル基、炭素原
子数１〜６のアルケニル基を表す。〕、 −Ｌ−OC(O)R12基〔但し、Ｌは前記と同様の意味を表
し、R12は炭素原子数１〜６のアルキル基または炭素原
子数１〜６のアルコキシ基を表す。〕、 −Ｌ−S(O)nR11基〔但し、Ｌ、ｎおよびR11は前記と同
様の意味を表す。〕、 −Ｌ−SC(O)R8基〔但し、ＬおよびR8は前記と同様の意
味を表す。〕、 〔但し、L1およびL2は互いに独立してメチレン、酸素原
子またはイオウ原子を表す。Q represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be substituted by a halogen atom, an alkenyl group having 1 to 6 carbon atoms which may be substituted by a halogen atom, A alkynyl group having 1 to 6 carbon atoms, a cyanomethyl group, a —C (O) —R 7 group [where R 7 is an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, An alkynyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a haloalkenyl group having 1 to 6 carbon atoms, a haloalkynyl group having 1 to 6 carbon atoms, a halogen atom, a nitro group or trifluoro. A phenyl group which may be substituted with the same or different substituent (s) selected from a methyl group,
Represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or a hydroxyl group. ], -S (O) 2 R 7 group [where, R 7 have the same meanings as defined above. ], -P (O) (OR 7 ) 2 groups, wherein R 7 has the same meaning as described above. ], -L-C (O) -R 7 group [where, L and R 7 have the same meanings as defined above. ] -L-C (O) -N ( R 8) (R 9) group [where, L is the same meanings as defined above. R 8 and R 9 independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ] -LR 10 groups [where L represents the same meaning as described above.] R 10 is a phenyl group which may be substituted with the same or different substituent (s) selected from a halogen atom, a nitro group or a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms and 1 to 6 carbon atoms. Represents an alkoxy group or a hydroxyl group. ], -L-N (R 8 ) (R 9 ) group [however, L, R 8 and R 9 represent the same meaning as described above. ], -L-OR 11 group [where L represents the same meaning as described above;
11 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkenyl group having 1 to 6 carbon atoms. ], -L-OC (O) R 12 group [where, L is the meaning similar to the above, R 12 represents an alkyl group or an alkoxy group having 1 to 6 carbon atoms having 1 to 6 carbon atoms. ], -L-S (O) n R 11 group [where, L, n and R 11 have the same meanings as defined above. ], -L-SC (O) R 8 group [where, L and R 8 have the same meanings as defined above. ], [However, L1 and L2 independently represent a methylene, an oxygen atom or a sulfur atom.
R12は水素原子または炭素原子数１〜３のアルキル基
を表す。ｍは２または３を表す〕〕 で表されるピラゾール誘導体およびその塩の１種または
２種以上を有効成分として含有することを特徴とする選
択性除草剤に関する。R 12 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. m represents 2 or 3]] and a selective herbicide characterized by containing one or more of a pyrazole derivative represented by the following formula and a salt thereof as an active ingredient.
本発明化合物の置換基Ａ、Ｂ、Ｘ、Ｙ、ＺおよびＱと
しては以下の置換基が好ましい。As the substituents A, B, X, Y, Z and Q of the compound of the present invention, the following substituents are preferred.
A:Me,Et,n−Pr,i−Pr,CH2CH＝CH2，CH2C≡CH B:H,Me,Et,n−Pr,i−Pr,Cl,Br,CH2Cl，CF3,OMe,OEt,OPr
−i,SMe,CH2OMe，CH2SMe，CO2Me，CO2Et X:Me,Et,n−Pr,i−Pr,n−Bu,i−Bu,s−Bu,t−Bu,OMe,OE
t,OPr−n,OPr−i,OBu−n,OBu−i,OBu−s,OBu−t,F,Cl,B
r,I,NO2,CN,CH2F，CHF2，CF3，CH2CF3，CH2Cl，CCl3,CH
ClMe,CH2CH2Cl，CHClCH2Cl，CH2Br,CHBrMe,CH2CH2Br，C
H2OMe，CH2OEt，CH2OPr−n,CH2OPr−i,CH2OBu−n,CH2OB
u−i,CH2OBu−s,CH2OBu−t,CHMeOMe,CHMeOEt,CHMeOPr−
n,CHMeOPr−i,CHMeOBu−n,CHMeOBu−i,CHMeOBu−s,CHMe
OBu−t,CH2CH2OMe，CH2CH2OEt，CH2CH2OPr−i,Ac,COEt,
COPr−n,COPr−i,COOMe,COOEt,COOPr−i,CONHMe,CONHE
t,CONMe2，CONEt2,CONEtMe,OCHF2，OCF3，OCH2CF3,SMe,
SEt,CH2SMe，CH2SEt,CHMeSMe,CHMeSEt OCHMeCH＝CH2，OCMe2CH＝CH2，OCH2CMe＝CH2，OCH2CH＝
CHMe,OCH2CH＝CMe2，OCH2C≡CH,OCHMeC≡CH,OCMe2C≡C
H,OCH2C≡CMe,OCH2CH2F，OCH2CHF2，OCH2CF3，OCH2CH2C
l，OCHMeCH2Cl，OCH2CCl3，OCH2CH2CH2Cl， OCH2CH2CH＝CH2， OCH2CCl＝CHCl,OCH2CH2NO2,OPh,OPh−Me−２ OPh-Cl−4,OPh-NO2−4, OCH2CH2OMe，OCH2CH2OEt，OCH2CH2OPr−n,OCH2CH2OPr−
i,OCH2CH2OBu−n,OCH2CH2OBu−i,OCH2CH2OBu−s,OCH2CH
2OBu−t,OCHMeCH2OMe，OCH2CH2OPh，OCH2CH2OCH2CH2OM
e，OCH2CH2OH，OCH2CH2OCHMeCH2OMe，OCH2Ph,OCHMePh, OCH2Ph−４−Me,OCH2Ph−４−Cl,OCH2CH2Ph， OCH2COOEt，OCH2COOPr−n,OCH2COOPr−i,OCH2COOBu−t,
OCHMeCOOMe,OCHMeCOOEt OCHMeCOOPr−n,OCHMeCOOPr−
i,OCHMeCOOBu−ｔ OCH2CH2CN，OCH2CN,OCHMeCN,OCH2SM
e，OCH2C(O)Ph，OCH2C(O)Me， OCH2CH2SMe，OCH2CH2SOMe，OCH2CH2SO2Me，OCH2CH2SE
t，OCH2CH2SO2Et,OCOOMe,OCOOEt,OCOOPr−i,OCONH2,OCO
NHMe,OCONMe2，OP(O)(OMe)2，OP(O)(OEt)2， SO2Ph，SO2CH2CH2OMe，SO2CH2CH2OEt，SO2CH2CH2OPr−
i, Z:F,Cl,Br,I,NO2,OMe,OEt,OPr−n,OPr−i,CF3,CN,SMe,S
OMe,SO2Me，SCF3，SOCF3，SO2CF3 Q:H,Me,Et,n−Pr,i−Pr,n−Bu,i−Bu,s−Bu,t−Bu,CH2C
H2Cl，CH2CF3,CHClMe,CH2CH2Br，CHClCH2Cl，CH2CH＝CH
2，CH2CMe＝CH2，CH2CH＝CHMe,CH2C≡CH,CH2CCl＝CH2，
CH2CN，CH2Ph，CH2Ph‐Cl−2, CH2Ph‐Me2-2,4,CH2Ph‐Me−4,CHMePh,CHEtPh,CH2Ph-NO
2−2,CH2Ph‐CF3−3,CH2OMe，CH2OEt，CH2OH,CHMeOH,CH
2NHMe，CH2NMe2，CHMeNMe2，CH2COPh，CH2COPh‐NO2−
4,CH2COPh‐Me−4,CH2COPh‐Cl−4,CH2COPh‐Me2-2,4,C
H2COPh‐CF3−4,CH2Ac，CH2COEt,CHMeAc,CH2CO2Me，CH2
CO2Et，CH2CO2Pr−n,CH2CO2Pr−i,CH2CO2Bu−t,CH2CO
2H，CHMeCO2H，CH2CONHMe，CH2CONMe2，CH2CONHEt，CH2
CONEt2，CH2CONPr-n2，CH2OCH2CH＝CH2，CH2OAc，CH2CO
Et，CH2COPr−i,CH2COBu−t,CH2OCO2Me，CH2OCO2Et，CH
2OCO2Pr−i,CH2OCO2Bu−t,CH2SMe，CH2SEt，CH2SCH2CH
＝CH2，CH2SAc，CH2SCOBu−t,CH2SO2Me，CH2SO2Et，CH2
SO2CH2CH＝CH2，CH2NHCH2CH＝CH2，CH2NMeCH2CH＝CH2，
CH2NHAc，CH2NHCOEt，CH2NHCO2Me，CH2NHCO2Et，CH2NMe
CO2Me,COPh,COPh-Me−4,COPh-NO2−2,COPh-Cl2-2,4,Ac,
COEt,COPr−n,COPr−i,COBu−n,COBu−t,COCH2Cl，COCH
Cl2，COCCl3，COCF3，COCH3OMe，COCH2OPh，COCH2CH＝C
HCH3，CO2Me，CO2Et，CO2Bu−t,CO2Pr−i,CONHMe,CONMe
2,CONHEt,CONEt2，CONPr-n2,CON（CH2CH＝CH2）2,CONMe
Ph, CO2CH2Ph，CO2Ph，SO2Me，SO2Et，SO2CH2CH＝CH2，SO2P
h，SO2Ph‐Me−4,SO2Ph‐Cl−4,SO2Ph‐(NO2)2-2,4,SO2
CF3,P（＝Ｏ）（OMe）2,P（＝Ｏ）（OEt）2,P（＝Ｏ）
（OPr−ｎ）2,P（＝Ｏ）（OPr−ｉ）2,P（＝Ｓ）（OM
e）2,P（＝Ｓ）（OEt）2,P（＝Ｏ）OMeOPh,P（＝Ｏ）
（OCH2CH＝2）2,P（＝Ｏ）OPhOCH2CH＝CH2 また、Ｑが水素原子で表わされる化合物の場合、金属
もしくは、有機塩基と容易に塩を形成する。A: Me, Et, n-Pr, i-Pr, CH 2 CH = CH 2 , CH 2 C≡CH B: H, Me, Et, n-Pr, i-Pr, Cl, Br, CH 2 Cl, CF 3 , OMe, OEt, OPr
−i, SMe, CH 2 OMe, CH 2 SMe, CO 2 Me, CO 2 Et X: Me, Et, n−Pr, i−Pr, n−Bu, i−Bu, s−Bu, t−Bu, OMe, OE
t, OPr-n, OPr-i, OBu-n, OBu-i, OBu-s, OBu-t, F, Cl, B
r, I, NO 2 , CN, CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CH 2 Cl, CCl 3 , CH
ClMe, CH 2 CH 2 Cl, CHClCH 2 Cl, CH 2 Br, CHBrMe, CH 2 CH 2 Br, C
H 2 OMe, CH 2 OEt, CH 2 OPr-n, CH 2 OPr-i, CH 2 OBu-n, CH 2 OB
u-i, CH 2 OBu- s, CH 2 OBu-t, CHMeOMe, CHMeOEt, CHMeOPr-
n, CHMeOPr-i, CHMeOBu-n, CHMeOBu-i, CHMeOBu-s, CHMe
OBu-t, CH 2 CH 2 OMe, CH 2 CH 2 OEt, CH 2 CH 2 OPr-i, Ac, COEt,
COPr-n, COPr-i, COOMe, COOEt, COOPr-i, CONHMe, CONHE
t, CONMe 2 , CONEt 2 , CONEtMe, OCHF 2 , OCF 3 , OCH 2 CF 3 , SMe,
SEt, CH 2 SMe, CH 2 SEt, CHMeSMe, CHMeSEt OCHMeCH = CH 2 , OCMe 2 CH = CH 2 , OCH 2 CMe = CH 2 , OCH 2 CH =
CHMe, OCH 2 CH = CMe 2 , OCH 2 C≡CH, OCHMeC≡CH, OCMe 2 C≡C
H, OCH 2 C≡CMe, OCH 2 CH 2 F, OCH 2 CHF 2 , OCH 2 CF 3 , OCH 2 CH 2 C
l, OCHMeCH 2 Cl, OCH 2 CCl 3 , OCH 2 CH 2 CH 2 Cl, OCH 2 CH 2 CH = CH 2 , OCH 2 CCl = CHCl, OCH 2 CH 2 NO 2 , OPh, OPh-Me-2 OPh-Cl-4, OPh-NO 2 -4, OCH 2 CH 2 OMe, OCH 2 CH 2 OEt, OCH 2 CH 2 OPr−n, OCH 2 CH 2 OPr−
i, OCH 2 CH 2 OBu-n, OCH 2 CH 2 OBu-i, OCH 2 CH 2 OBu-s, OCH 2 CH
2 OBu-t, OCHMeCH 2 OMe, OCH 2 CH 2 OPh, OCH 2 CH 2 OCH 2 CH 2 OM
e, OCH 2 CH 2 OH, OCH 2 CH 2 OCHMeCH 2 OMe, OCH 2 Ph, OCHMePh, OCH 2 Ph-4-Me, OCH 2 Ph-4-Cl, OCH 2 CH 2 Ph, OCH 2 COOEt, OCH 2 COOPr-n, OCH 2 COOPr-i, OCH 2 COOBu-t,
OCHMeCOOMe, OCHMeCOOEt OCHMeCOOPr-n, OCHMeCOOPr-
i, OCHMeCOOBu-t OCH 2 CH 2 CN, OCH 2 CN, OCHMeCN, OCH 2 SM
e, OCH 2 C (O) Ph, OCH 2 C (O) Me, OCH 2 CH 2 SMe, OCH 2 CH 2 SOMe, OCH 2 CH 2 SO 2 Me, OCH 2 CH 2 SE
t, OCH 2 CH 2 SO 2 Et, OCOOMe, OCOOEt, OCOOPr-i, OCONH 2 , OCO
NHMe, OCONMe 2 , OP (O) (OMe) 2 , OP (O) (OEt) 2 , SO 2 Ph, SO 2 CH 2 CH 2 OMe, SO 2 CH 2 CH 2 OEt, SO 2 CH 2 CH 2 OPr−
i, Z: F, Cl, Br, I, NO 2, OMe, OEt, OPr-n, OPr-i, CF 3, CN, SMe, S
OMe, SO 2 Me, SCF 3 , SOCF 3 , SO 2 CF 3 Q: H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH 2 C
H 2 Cl, CH 2 CF 3 , CHClMe, CH 2 CH 2 Br, CHClCH 2 Cl, CH 2 CH = CH
2 , CH 2 CMe = CH 2 , CH 2 CH = CHMe, CH 2 C≡CH, CH 2 CCl = CH 2 ,
CH 2 CN, CH 2 Ph, CH 2 Ph-Cl-2, CH 2 Ph-Me 2 -2,4, CH 2 Ph-Me-4, CHMePh, CHEtPh, CH 2 Ph-NO
2 -2, CH 2 Ph-CF 3 -3, CH 2 OMe, CH 2 OEt, CH 2 OH, CHMeOH, CH
2 NHMe, CH 2 NMe 2 , CHMeNMe 2 , CH 2 COPh, CH 2 COPh-NO 2 −
4, CH 2 COPh-Me-4, CH 2 COPh-Cl-4, CH 2 COPh-Me 2 -2,4, C
H 2 COPh-CF 3 -4, CH 2 Ac, CH 2 COEt, CHMeAc, CH 2 CO 2 Me, CH 2
CO 2 Et, CH 2 CO 2 Pr-n, CH 2 CO 2 Pr-i, CH 2 CO 2 Bu-t, CH 2 CO
2 H, CHMeCO 2 H, CH 2 CONHMe, CH 2 CONMe 2 , CH 2 CONHEt, CH 2
CONEt 2 , CH 2 CONPr-n 2 , CH 2 OCH 2 CH = CH 2 , CH 2 OAc, CH 2 CO
Et, CH 2 COPr-i, CH 2 COBu-t, CH 2 OCO 2 Me, CH 2 OCO 2 Et, CH
2 OCO 2 Pr-i, CH 2 OCO 2 Bu-t, CH 2 SMe, CH 2 SEt, CH 2 SCH 2 CH
= CH 2, CH 2 SAc, CH 2 SCOBu-t, CH 2 SO 2 Me, CH 2 SO 2 Et, CH 2
SO 2 CH 2 CH = CH 2 , CH 2 NHCH 2 CH = CH 2 , CH 2 NMeCH 2 CH = CH 2 ,
CH 2 NHAc, CH 2 NHCOEt, CH 2 NHCO 2 Me, CH 2 NHCO 2 Et, CH 2 NMe
CO 2 Me, COPh, COPh-Me-4, COPh-NO 2 -2, COPh-Cl 2 -2,4, Ac,
COEt, COPr-n, COPr- i, COBu-n, COBu-t, COCH 2 Cl, COCH
Cl 2 , COCCl 3 , COCF 3 , COCH 3 OMe, COCH 2 OPh, COCH 2 CH = C
HCH 3 , CO 2 Me, CO 2 Et, CO 2 Bu-t, CO 2 Pr-i, CONHMe, CONMe
2 , CONHEt, CONEt 2 , CONPr-n 2 , CON (CH 2 CH = CH 2 ) 2 , CONMe
Ph, CO 2 CH 2 Ph, CO 2 Ph, SO 2 Me, SO 2 Et, SO 2 CH 2 CH = CH 2 , SO 2 P
h, SO 2 Ph-Me-4, SO 2 Ph-Cl-4, SO 2 Ph- (NO 2 ) 2 -2,4, SO 2
CF 3 , P (= O) (OMe) 2 , P (= O) (OEt) 2 , P (= O)
(OPr-n) 2 , P (= O) (OPr-i) 2 , P (= S) (OM
e) 2 , P (= S) (OEt) 2 , P (= O) OMeOPh, P (= O)
(OCH 2 CH = 2 ) 2 , P (＝ O) OPhOCH 2 CH ＝ CH 2 When Q is a hydrogen atom, it easily forms a salt with a metal or an organic base.
金属としてはナトリウム、カリウム、カルシウム、リ
チウム、バリウム、マグネシウム、鉄、銅、ニッケル、
マンガンなどがあげられる。Metals include sodium, potassium, calcium, lithium, barium, magnesium, iron, copper, nickel,
Manganese and the like.
有機塩基としては、メチルアミン，ジメチルアミン，
トリメチルアミン，エチルアミン，ジエチルアミン，ト
リエチルアミン，ノルマルプロピルアミン，ジノルマル
プロピルアミン，イソプロピルアミン，ジイソプロピル
アミン、ノルマルチルアミン，イソブチルアミン，セカ
ンダリーブチルアミン，ターシャリーブチルアミン，ピ
ペリジン，ピロリジン，モルホリン，ピリジン,N,N−ジ
メチルアニリン，コリンなどがあげられる。Organic bases include methylamine, dimethylamine,
Trimethylamine, ethylamine, diethylamine, triethylamine, normal propylamine, dinormal propylamine, isopropylamine, diisopropylamine, normartilamine, isobutylamine, secondary butylamine, tertiary butylamine, piperidine, pyrrolidine, morpholine, pyridine, N, N-dimethyl Examples include aniline and choline.
本発明者等は、有用な除草剤の開発を目的に各種有機
化合物の除草特性に関する研究を進める中で、前記の本
発明化合物が、禾木科植物（イネ科およびカヤツリグサ
科）および各種広葉雑草に対し卓越した殺草効力を有
し、かつ有用作物、例えばトーモロコシ、ソルガム、コ
ムギ、オオムギ等の栽培作物に対しては実質上無害であ
るという知見を得、本発明を完成した。The present inventors have been conducting research on the herbicidal properties of various organic compounds for the purpose of developing useful herbicides. The present inventors have found that they have excellent herbicidal activity and that they are substantially harmless to useful crops such as cultivated crops such as corn, sorghum, wheat, and barley, and thus completed the present invention.
本発明化合物は、土壌処理、土壌混和処理および茎葉
処理のいずれでも、強い除草活性を示し、一方栽培作
物、例えばトーモロコシ、ソルガム、コムギ、オオムギ
等に対しては土壌処理、土壌混和処理および茎葉処理の
いずれの方法でも、実用上、薬害が全く認められず、高
度の選択性を有するもので、これらの作物の栽培時にお
ける雑草防除には、極めて有効である。すなわち、トー
モロコシ、ソルガム栽培時に発生する有害雑草のエノコ
ログサ、ノビエ、イヌビユ、イヌタデ、オナモミ、イチ
ビ、ハマスゲ等に対して強い殺草活性を示すものであ
る。特にイネ科雑草及びハマスゲ類に対する除草活性は
著しく高く、極めてユニークである。従来、トーモロコ
シやソルガムの栽培時にはトリアジン系の除草剤である
アトラジンやシアナジン、酸アニライド系の除草剤であ
るアラクロールおよびメトラクロールが用いられてき
た。しかしながらアトラジンやシアナジンは広葉雑草に
は高い活性を示すが、イネ科雑草に対する活性が低く、
またハマスゲ類に対する活性は著しく低い。The compound of the present invention shows strong herbicidal activity in any of soil treatment, soil admixture treatment and foliage treatment, while soil treatment, soil admixture treatment and foliage treatment for cultivated crops such as corn, sorghum, wheat, barley and the like. Both methods have practically no phytotoxicity and high selectivity, and are extremely effective in controlling weeds during cultivation of these crops. In other words, it shows strong herbicidal activity against corn, harmful weeds generated during cultivation of sorghum, such as enokorogusa, nobie, inuyubu, inutake, onamimi, ibis, and locust. In particular, the herbicidal activity against grasses and weeds is remarkably high, and is very unique. Conventionally, at cultivation of corn and sorghum, triazine-based herbicides atrazine and cyanazine, and acid anilide-based herbicides alachlor and metolachlor have been used. However, atrazine and cyanazine have high activity on broadleaf weeds but low activity on grass weeds,
In addition, the activity against hummus is extremely low.
一方、アラクロールやメトラクロールではイネ科に対
する活性は高いが、広葉雑草に対する活性は低く、また
ハマスゲに対する活性は極めて不充分である。従って、
すべての雑草種を一回の薬剤処理で撲滅することは至難
であった。On the other hand, arachlor and metolachlor have a high activity against grasses, but a low activity against broadleaf weeds, and have an extremely insufficient activity against nutsedge. Therefore,
Eradication of all weed species with a single drug treatment was very difficult.
本発明者らは、種々検討を重ねてきた結果、広範囲の
雑草に効力を示す本発明化合物を見い出し、本発明を完
成するに至った。また、本発明化合物は、トーモコロ
シ、ソルガム、コムギ、オオムギに対する薬害が全くな
く完全に使用できるという効果も有するものである。The present inventors have made various studies, and as a result, have found a compound of the present invention that is effective against a wide range of weeds, and have completed the present invention. Further, the compound of the present invention has an effect that it can be completely used without any phytotoxicity against corn, sorghum, wheat, and barley.
さらに、本発明化合物には、イネ−ヒエ間の選択性を
示す化合物も含まれ、また、ワタ、ビート、ダイズ、ナ
タネなどの有用作物に選択性を有する化合物も含まれ
る。Further, the compound of the present invention includes a compound showing selectivity between rice and barley, and also includes a compound having selectivity for useful crops such as cotton, beet, soybean, and rape.
従来、４−ベンゾイルピラゾール誘導体が、すぐれた
除草活性を有することは知られており例えばピラゾレー
ト（一般名）が支配され、広く実用に供されている。し
かしこれらはいずれも実用場面としては水田に限定され
ており、畑条件では著しく活性が低下する。しかしなが
ら本発明者らは４−ベンゾイルピラゾール誘導体につい
て長年研究を重ねた結果、上記の本発明化合物の構造式
の置換基の条件を同時に満たす場合に、畑条件において
土壌処理、土壌混和処理、茎葉処理のいずれでも強力な
除草活性を発現し、特に、イネ科雑草及びハマスゲ類に
は著しく高い活性を示すことも見出した。Heretofore, it has been known that 4-benzoylpyrazole derivatives have excellent herbicidal activity. For example, pyrazolate (common name) is dominant and widely used. However, all of these are practically limited to paddy fields, and their activity is significantly reduced under field conditions. However, as a result of many years of research on the 4-benzoylpyrazole derivative, the present inventors have found that when the above-mentioned conditions for the substituents of the structural formula of the compound of the present invention are simultaneously satisfied, soil treatment, soil admixture treatment, foliage treatment under field conditions are required. It was also found that any of these exhibited a strong herbicidal activity, and in particular, exhibited a remarkably high activity on grasses and weeds.
本発明化合物は例えば下記の反応式のいずれかによっ
て容易に合成される。The compound of the present invention is easily synthesized, for example, by any of the following reaction formulas.
（式中A,B,V,W,X,Y,ZおよびＱは前記と同じ意味を表
わし、Ｅはハロゲン原子、メタンスルホニルオキシ基ま
たはパラトルエンスルホニルオキシ基を表わす。さらに と互変異性体であり、いずれの構造式で表わすこともで
きる。） 反応式（１）は、それぞれ適当な置換基を有する安息
香酸と５−ヒドロキシピラゾールを、縮合剤及び塩基の
存在下、不活性溶媒中で反応させて４−ベンゾイル−５
−ヒドロキシピラゾールを得る反応を表わす。縮合剤は
安息香酸及びピラゾールに対し1.0〜1.5倍モル用いるの
が望ましい。縮合剤としては、例えばN,N′−ジシクロ
ヘキシルカルボジイミドがあげられる。溶媒は反応に不
活性であればいずれでもよいが、特にターシャリブチル
アルコール、ターシャリアミルアルコール、イソプロピ
ルアルコールなどがすぐれる。塩基は必ずしも必要とし
ないが一般に使用することにより、収率が向上する。特
に限定はないが炭酸カリウム、炭酸ナトリウムなどがす
ぐれる。反応温度は室温から溶媒の沸点までいずれでも
可能であるが、50〜100℃程度が望ましい。反応時間は
通常0.5〜20時間程度である。 (Wherein A, B, V, W, X, Y, Z and Q have the same meaning as described above, and E represents a halogen atom, a methanesulfonyloxy group or a paratoluenesulfonyloxy group. And can be represented by any structural formula. In the reaction formula (1), 4-benzoyl-5 is obtained by reacting benzoic acid having an appropriate substituent with 5-hydroxypyrazole in an inert solvent in the presence of a condensing agent and a base.
-Reaction to obtain hydroxypyrazole. The condensing agent is desirably used in an amount of 1.0 to 1.5 times the molar amount of benzoic acid and pyrazole. Examples of the condensing agent include N, N'-dicyclohexylcarbodiimide. The solvent may be any as long as it is inert to the reaction, but tertiary butyl alcohol, tertiary milk alcohol, isopropyl alcohol and the like are particularly excellent. Although a base is not necessarily required, its use generally improves the yield. Although not particularly limited, potassium carbonate, sodium carbonate and the like are excellent. The reaction temperature can be any from room temperature to the boiling point of the solvent, but is preferably about 50 to 100 ° C. The reaction time is usually about 0.5 to 20 hours.
反応式（２）はそれぞれ適当な置換基を有するベンゾ
イルクロリドと５−ヒドロキシピラゾールとより、ベン
ゾイルエステルとしこれを転位させて４−ベンゾイル体
とる反応を示す。The reaction formula (2) shows a reaction in which benzoyl chloride having an appropriate substituent and 5-hydroxypyrazole are converted into a benzoyl ester and rearranged to form a 4-benzoyl compound.
ベンゾイルエステル化は反応に不活性な溶媒（芳香族
炭化水素類、脂肪酸エステル類、ハロゲン化炭化水素
類、エーテル類、アセトニトリル、ジメチルスルホキシ
ド、N,N′−ジメチルホルムアミドなど）中、またはそ
れらと水との二相系や混合系中で、適当な脱塩化水素剤
（苛性ソーダ、苛性カリ、炭酸水素ナトリウムなどの無
機塩基、ピリジン、トリエチルアミンなどの有効塩基）
存在下、室温ないし100℃で通常10分から５時間で達成
される。Benzoyl esterification is carried out in a solvent inert to the reaction (such as aromatic hydrocarbons, fatty acid esters, halogenated hydrocarbons, ethers, acetonitrile, dimethyl sulfoxide, N, N'-dimethylformamide, etc.) or in water. Suitable dehydrochlorinating agents (inorganic bases such as caustic soda, caustic potash, sodium bicarbonate, and effective bases such as pyridine and triethylamine)
It is usually achieved in the presence at room temperature to 100 ° C. in 10 minutes to 5 hours.
転位反応は無水塩化アルミニウムに代表されるルイス
酸または塩基によって達成される。塩基としては炭酸カ
リウム、水酸化カルシウム、炭酸ナトリウム等が使用さ
れる。The rearrangement reaction is achieved by a Lewis acid or base typified by anhydrous aluminum chloride. As the base, potassium carbonate, calcium hydroxide, sodium carbonate and the like are used.
ルイス酸も塩基も通常１〜10倍モル使用される。 The Lewis acid and the base are usually used in a molar amount of 1 to 10 times.
溶媒は特には必要としないが反応に不活性であり、適
当な沸点をもつものは操作性、収率などを向上させる場
合がある。好適な例としてジオキサン、ジグライム、ト
ルエン、キシレンなどがあげられる。A solvent is not particularly required, but is inert to the reaction, and a solvent having an appropriate boiling point may improve operability, yield and the like. Preferred examples include dioxane, diglyme, toluene, xylene and the like.
反応温度は通常50〜150℃、反応時間は15分〜30時間
である。The reaction temperature is usually 50 to 150 ° C, and the reaction time is 15 minutes to 30 hours.
反応式（３）は、ベンゼン誘導体、５−ヒドロキシピ
ラゾール誘導体および四塩化炭素をルイス酸の存在下、
無溶媒または不活性溶媒中で縮合させ、次いで加水分解
して４−ベンゾイル−５−ヒドロキシピラゾール誘導体
を得る反応を表す。ルイス酸としては反応理論量以上の
無水塩化アルミニウム、無水臭化アルミニウムなどが望
ましい。溶媒は反応に不活性であれば何れでもよいが、
塩素系溶媒、たとえば塩化メチレン、ジクロロエタン、
テトラクロロエタンなどが優れる。縮合温度は０℃から
溶媒の沸点までが可能であるが10〜80℃が望ましい。加
水分解反応は塩酸または硫酸の存在下で行われる。反応
温度は室温から100℃が望ましく、反応時間は通常0.1〜
10時間である。The reaction formula (3) is obtained by converting a benzene derivative, a 5-hydroxypyrazole derivative and carbon tetrachloride in the presence of a Lewis acid.
This represents a reaction in which condensation is performed in a solvent-free or inert solvent, and then hydrolysis is performed to obtain a 4-benzoyl-5-hydroxypyrazole derivative. As the Lewis acid, anhydrous aluminum chloride, anhydrous aluminum bromide and the like in a stoichiometric amount or more are desirable. The solvent may be any as long as it is inert to the reaction,
Chlorinated solvents such as methylene chloride, dichloroethane,
Tetrachloroethane is excellent. The condensation temperature can range from 0 ° C to the boiling point of the solvent, but is preferably from 10 to 80 ° C. The hydrolysis reaction is performed in the presence of hydrochloric acid or sulfuric acid. The reaction temperature is preferably from room temperature to 100 ° C, and the reaction time is usually 0.1 to
10 hours.
反応式（４）はシアン化ベンゾイル誘導体と５−ヒド
ロキシピラゾール誘導体をルイス酸および塩基の存在下
で、無溶媒または不活性溶媒中で反応させて４−ベンゾ
イル５−ヒドロキシピラゾールを得る反応を表す。ルイ
ス酸としては塩化亜鉛、塩化アルミニウム、臭化アルミ
ニウムなどがあげられる。塩基としては、ピリジン、ト
リエチルアミンなどがあげられる。ルイス酸も塩基も通
常１〜10倍モル使用される。溶媒は塩化メチレン、ジク
ロロエタン、テトラクロロエタンなどがあげられる。反
応温度は０〜80℃、好ましくは10〜50℃である。反応時
間は0.5〜20時間である。Reaction formula (4) represents a reaction in which a benzoyl cyanide derivative and a 5-hydroxypyrazole derivative are reacted in the presence of a Lewis acid and a base in a solvent-free or inert solvent to obtain 4-benzoyl5-hydroxypyrazole. Examples of the Lewis acid include zinc chloride, aluminum chloride, and aluminum bromide. Examples of the base include pyridine, triethylamine and the like. The Lewis acid and the base are usually used in a molar amount of 1 to 10 times. Examples of the solvent include methylene chloride, dichloroethane, tetrachloroethane and the like. The reaction temperature is 0 to 80 ° C, preferably 10 to 50 ° C. The reaction time is between 0.5 and 20 hours.
反応式（５）は４−ベンゾイル−５−ヒドロキシピラ
ゾールとハライド類、メタンスルホン酸エステルまたは
ｐ−トルエンスルホン酸エステルとを縮合させる反応を
示す。Reaction formula (5) shows a reaction for condensing 4-benzoyl-5-hydroxypyrazole with a halide, methanesulfonic acid ester or p-toluenesulfonic acid ester.
この反応には１〜３倍モルの脱ハロゲン化水素剤を使
用することが望ましい。脱ハロゲン化水素剤としては苛
性ソーダ、苛性カリ、炭酸ナトリウム、炭酸水素ナトリ
ウム、炭酸カリウムなどの無機塩基、ピリジン、トリエ
チルアミンなどの有機塩基があげられる。It is desirable to use 1 to 3 moles of a dehydrohalogenating agent for this reaction. Examples of the dehydrohalogenating agent include inorganic bases such as caustic soda, caustic potash, sodium carbonate, sodium bicarbonate and potassium carbonate, and organic bases such as pyridine and triethylamine.
溶媒は反応に不活性であれば特に限定はなく、芳香族
炭化水素類、脂肪族エステル類、ハロゲン化炭化水素
類、エーテル類、ケトン類、脂肪族炭化水素類、アセト
ニトリル、ジメチルスルホキシド、ジメチルホルムアミ
ドなど広く使用されうる。The solvent is not particularly limited as long as it is inert to the reaction. Aromatic hydrocarbons, aliphatic esters, halogenated hydrocarbons, ethers, ketones, aliphatic hydrocarbons, acetonitrile, dimethylsulfoxide, dimethylformamide It can be widely used.
反応温度は室温から溶媒の沸点まで任意に選択するこ
とができ、反応時間は通常30分〜30時間程度である。The reaction temperature can be arbitrarily selected from room temperature to the boiling point of the solvent, and the reaction time is usually about 30 minutes to 30 hours.
反応式（６）は４−ベンゾイル−５−ヒドロキシピラ
ゾールをハロゲン化剤で５−ハロゲノ体とした後、ある
いはメタンスルホニルクロリドもしくはｐ−トルエンス
ルホニルクロリドによってメタンスルホネート体もしく
はｐ−トルエンスルホネート体とした後、適当なアルコ
ールまたは酸と縮合させる反応を示す。In the reaction formula (6), 4-benzoyl-5-hydroxypyrazole is converted into a 5-halogeno form with a halogenating agent, or after methanesulfonyl chloride or p-toluenesulfonyl chloride is converted into a methanesulfonate form or a p-toluenesulfonate form. , A condensation reaction with an appropriate alcohol or acid.
ハロゲン化剤としてはオキシ塩化リン、五塩化リン、
チオニルクロリドなどをあげることができる。Phosphorus oxychloride, phosphorus pentachloride,
Thionyl chloride and the like.
溶媒としてはジメチルホルムアミドなど反応に不活性
な溶媒を広く使用でき、無溶媒でもよい。As the solvent, a solvent inert to the reaction such as dimethylformamide can be widely used, and may be solventless.
反応温度は30〜150℃程度が望ましく、反応時間は30
分〜10時間程度であるが、脱ハロゲン化水素剤の添加で
時間の短縮、収率の向上がはかられる場合もある。The reaction temperature is preferably about 30 to 150 ° C, and the reaction time is about 30 ° C.
The time is about 10 minutes to 10 hours, but the addition of the dehydrohalogenating agent may shorten the time and improve the yield in some cases.
アルコールまたは酸との縮合反応は脱ハロゲン化水素
剤を添加する。The condensation reaction with an alcohol or acid adds a dehydrohalogenating agent.
脱ハロゲン化水素剤としては苛性ソーダ、苛性カリ、
炭酸ナトリウム、炭酸カリウム、ナトリウムアルコキシ
ド、水素化ナトリウムなどの塩基が用いられる。As dehydrohalogenating agents, caustic soda, caustic potash,
Bases such as sodium carbonate, potassium carbonate, sodium alkoxide, sodium hydride and the like are used.
溶媒は反応に不活性な溶媒（例えば芳香族炭化水素
類、エーテル類、ケトン類、N,N′−ジメチルホルムア
ミドなど）を用いることができ温度は室温から溶媒の沸
点までの間で可能である。As the solvent, a solvent inert to the reaction (eg, aromatic hydrocarbons, ethers, ketones, N, N'-dimethylformamide, etc.) can be used, and the temperature can be from room temperature to the boiling point of the solvent. .
本発明化合物の原料となる置換ベンゼン誘導体は何れ
も新規な構造をもち、種々の既知の合成法の組み合わせ
により、容易に合成が可能である。Each of the substituted benzene derivatives used as a raw material of the compound of the present invention has a novel structure, and can be easily synthesized by a combination of various known synthesis methods.
ベンゼン環の置換基ＺがS(O)nCH3の化合物において一
例を示せば下記の反応式に従って製造できる。An example of a compound in which the substituent Z on the benzene ring is S (O) nCH 3 can be produced according to the following reaction formula.
（上記式中、ＸおよびＹは前記と同じ意味を表し、Ha
lはハロゲン原子を表す。）などが挙げられる。 (In the above formula, X and Y represent the same meaning as described above;
l represents a halogen atom. ).
次に置換ベンゼン誘導体およびピラゾール誘導体の合
成を実施例をあげて詳細に説明するが、本発明はこれら
のよって限定されるものではない。Next, the synthesis of the substituted benzene derivative and the pyrazole derivative will be described in detail with reference to examples, but the present invention is not limited thereto.
実施例１ ４−（２−クロロ−４−メタンスルホニル−３−（２−
メトキシ）エトキシベンゾイル）−１−エチル−５−ヒ
ドロキシピラゾールの合成 （１） ２−クロロ−４−メタンスルホニル−３−（２
−メトキシ）エトキシ安息香酸（２−メトキシ）エチル ２−クロロ−３−ヒドロキシ−４−メタンスルホニル
安息香酸1.2g、炭酸カリウム1.4gおよび２−ブロモエチ
ルメチルエーテル2.1gをN,N−ジメチルホルムアミド20m
l中に入れ、60〜70°で６〜７時間加熱反応させ、溶媒
を留去した後、水を加えクロロホルム抽出した。これを
無水硫酸ナトリウムで乾燥後、溶媒を留去して粗製の目
的物1.9gを得た。Example 1 4- (2-chloro-4-methanesulfonyl-3- (2-
Synthesis of methoxy) ethoxybenzoyl) -1-ethyl-5-hydroxypyrazole (1) 2-chloro-4-methanesulfonyl-3- (2
(Methoxy) ethoxy (2-methoxy) ethyl benzoate 1.2 g of 2-chloro-3-hydroxy-4-methanesulfonylbenzoic acid, 1.4 g of potassium carbonate and 2.1 g of 2-bromoethyl methyl ether in N, N-dimethylformamide 20 m
Then, the mixture was heated and reacted at 60-70 ° for 6-7 hours. After the solvent was distilled off, water was added and the mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the solvent was distilled off to obtain 1.9 g of a crude target product.
（２） ２−２−クロロ−４−メタンスルホニル−３−
（２−メトキシ）エトキシ安息香酸 ２−クロロ−４−メタンスルホニル−３−（２−メト
キシ）エトキシ安息香酸（２−メトキシ）エチルの粗物
1.9gをエタノール50mlに溶解し、これに水酸化ナトリウ
ム1gの水溶液20mlを加えた。室温で30分間撹拌した後、
エタノールを留去し、水を加えた。これをクロロホルム
洗浄した後、濃塩酸で酸性にし、クロロホルムで抽出し
た。これを無水硫酸ナトリウムで乾燥後、溶媒を留去し
て粗製の目的物1.4gを得た。粗製物にｎ−ヘキサンを加
え、放置すると次第に目的物が結晶化した。(2) 2-2-chloro-4-methanesulfonyl-3-
(2-Methoxy) ethoxybenzoic acid 2-chloro-4-methanesulfonyl-3- (2-methoxy) ethoxybenzoic acid (2-methoxy) ethyl crude product
1.9 g was dissolved in 50 ml of ethanol, and 20 ml of an aqueous solution of 1 g of sodium hydroxide was added thereto. After stirring at room temperature for 30 minutes,
The ethanol was distilled off and water was added. This was washed with chloroform, made acidic with concentrated hydrochloric acid, and extracted with chloroform. After drying over anhydrous sodium sulfate, the solvent was distilled off to obtain 1.4 g of a crude target product. N-Hexane was added to the crude product, and the target product gradually crystallized on standing.
融点89〜92℃ （３） ４−（２−クロロ−４−メタンスルホニル−３
−（２−メトキシ）エトキシベンゾイル）−１−エチル
−５−ヒドロキシピラゾール ２−クロロ−４−メタンスルホニル−３−（２−メト
キシ）エトキシ安息香酸の粗物1.2g、炭酸カリウム0.3
g、１−エチル−５−ヒドロキシピラゾール0.45gおよび
N,N′−ジシクロヘキシルカルボジイミド0.77gをｔ−ア
ミルアルコール液40ml中に入れ、80〜90°で４〜５時間
加熱撹拌した。溶媒を留去した後、希炭酸カリウム水溶
液を加えて、クロロホルムで洗浄した。水層を濃塩酸で
酸性にし、クロロホルムで抽出した。これを無水硫酸ナ
トリウムで乾燥後、溶媒を留去し、粗製の目的物を得
た。エタノールで再結晶することにより目的物0.3gを得
た。融点159〜160℃ 実施例２ ４−（３−ベンジルオキシ−２−クロロ−４−メタンス
ルホニルベンゾイル）−１−エチル−５−ヒドロキシピ
ラゾールの合成 （１） ３−ベンジルオキシ−２−クロロ−４−メタン
スルホニル安息香酸ベンジル ２−クロロ−３−ヒドロキシ−４−メタンスルホニル
安息香酸1.5g、炭酸カリウム1.7gおよびベンジルブロマ
イド5.1gをDMF 50ml中に入れ、室温で一晩撹拌した後、
60〜70°で３時間加熱した。溶媒を留去した後、水を加
え、クロロホルムにて抽出した。これを無水硫酸ナトリ
ウムで乾燥後、溶媒を留去して粗製の目的物を得た。エ
タノール中で再結晶することにより目的物2.5gを得た。89-92 ° C (3) 4- (2-chloro-4-methanesulfonyl-3)
-(2-methoxy) ethoxybenzoyl) -1-ethyl-5-hydroxypyrazole 1.2 g of crude 2-chloro-4-methanesulfonyl-3- (2-methoxy) ethoxybenzoic acid, potassium carbonate 0.3
g, 0.45 g of 1-ethyl-5-hydroxypyrazole and
0.77 g of N, N'-dicyclohexylcarbodiimide was put in 40 ml of t-amyl alcohol solution, and the mixture was heated and stirred at 80 to 90 ° for 4 to 5 hours. After the solvent was distilled off, a diluted potassium carbonate aqueous solution was added, and the mixture was washed with chloroform. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with chloroform. After drying this over anhydrous sodium sulfate, the solvent was distilled off to obtain a crude target product. Recrystallization from ethanol yielded 0.3 g of the desired product. Melting point: 159 to 160 ° C. Example 2 Synthesis of 4- (3-benzyloxy-2-chloro-4-methanesulfonylbenzoyl) -1-ethyl-5-hydroxypyrazole (1) 3-benzyloxy-2-chloro-4 -Benzyl methanesulfonylbenzoate 1.5 g of 2-chloro-3-hydroxy-4-methanesulfonylbenzoic acid, 1.7 g of potassium carbonate and 5.1 g of benzylbromide in 50 ml of DMF, and stirred at room temperature overnight,
Heat at 60-70 ° for 3 hours. After the solvent was distilled off, water was added, and the mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the solvent was distilled off to obtain a crude target product. Recrystallization in ethanol gave 2.5 g of the desired product.
（２） ３−ベンジルオキシ−２−クロロ−４−メタン
スルホニル安息香酸 ３−ベンジルオキシ−２−クロロ−４−メタンスルホ
ニル安息香酸ベンジル2.5gをエタノール50mlに入れ、こ
れに水酸化ナトリウム1gの水溶液25mlを加えた。室温で
30分間撹拌した後、エタノールを留去し、水を加え、ク
ロロホルムで洗浄した。水層を濃塩酸で酸性にし、クロ
ロホルムで抽出した。これを無水硫酸ナトリウムで乾燥
後、溶媒を留去して、粗製の目的物を得た。エタノール
−イソプロピルエーテルで洗浄し、目的物1.0gを得た。(2) 3-benzyloxy-2-chloro-4-methanesulfonylbenzoic acid 2.5 g of benzyl 3-benzyloxy-2-chloro-4-methanesulfonylbenzoate was placed in 50 ml of ethanol, and an aqueous solution of 1 g of sodium hydroxide was added thereto. 25 ml were added. At room temperature
After stirring for 30 minutes, ethanol was distilled off, water was added, and the mixture was washed with chloroform. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with chloroform. After drying over anhydrous sodium sulfate, the solvent was distilled off to obtain a crude target product. Washing with ethanol-isopropyl ether gave 1.0 g of the desired product.
（３） ３−ベンジルオキシ−２−クロロ−４−メタン
スルホニル安息香酸1.0g、炭酸カリウム0.23g、１−エ
チル−５−ヒドロキシ−ピラゾール0.24gおよびN,N′−
ジシクロヘキシルカルボジイミド0.59gをｔ−アミルア
ルコール20ml中に入れ、80〜90°で４時間加熱撹拌し
た。溶媒を留去した後、炭酸カリウム水溶液を加え、ク
ロロホルムで洗浄した。水層と濃塩酸で酸性にした後、
クロロホルムで抽出した。これを無水硫酸ナトリウムで
乾燥後、溶媒を留去し、粗製の目的物を得た。これをエ
タノール中で再結晶することにより目的物0.3gを得た。
融点162〜165℃ 前記実施例に準じて合成した安息香酸類およびピラゾ
ール誘導体の物性値を前記実施例を含めて第１表及び第
２表に示す。(3) 3-benzyloxy-2-chloro-4-methanesulfonylbenzoic acid 1.0 g, potassium carbonate 0.23 g, 1-ethyl-5-hydroxy-pyrazole 0.24 g and N, N'-
0.59 g of dicyclohexylcarbodiimide was placed in 20 ml of t-amyl alcohol, and heated and stirred at 80 to 90 ° for 4 hours. After the solvent was distilled off, an aqueous potassium carbonate solution was added, and the mixture was washed with chloroform. After acidifying with aqueous layer and concentrated hydrochloric acid,
Extracted with chloroform. After drying this over anhydrous sodium sulfate, the solvent was distilled off to obtain a crude target product. This was recrystallized in ethanol to obtain 0.3 g of the desired product.
Melting point: 162 to 165 ° C. Physical properties of benzoic acids and pyrazole derivatives synthesized according to the above Examples are shown in Tables 1 and 2 including the above Examples.
次に前記実施例に準じて合成される化合物を前記実施
例を含めて第３表〜第８表に示す。ただし本発明はこれ
らのみに限定されるものではない。 Next, Tables 3 to 8 show the compounds synthesized according to the above Examples, including the Examples. However, the present invention is not limited only to these.
ただし第３表〜第８表で使用される記号は以下の意味
を表す。However, the symbols used in Tables 3 to 8 represent the following meanings.
本発明化合物を農園芸用除草剤として使用するにあた
っては，一般には適当な担体，例えばクレー，タルク，
ベントナイト，珪藻土等の固体担体あるいは水，アルコ
ール類（メタノール，エタノール等），芳香族炭化水素
類（ベンゼン，トルエン，キシレン等），塩素化炭化水
素類，エーテル類，ケトン類，エステル類（酢酸エチル
等），酢アミド類（ジメチルホルムアミド等）などの液
体担体と混用して適用することができ，所望により乳化
剤，分散剤，懸濁剤，浸透剤，展着剤，安定剤などを添
加し，液剤，乳剤，水和剤，粉剤，粒剤，フロアブル剤
等任意の剤型にて実用に供することができる。また，必
要に応じて製剤または撒布時に他種の除草剤，各種殺虫
剤，殺菌剤，植物生長調節剤，共力剤などと混合施用し
てもよい。混合する除草剤の種類としては，例えば，フ
ァーム・ケミカルズ・ハンドブック（Farm Chemicals H
andbook），第73版（1987）に記載されている化合物な
どがある。その中からいくつかを挙げれば、アトラジ
ン、シアナジン、アラクロール、メトラクロール、EPT
C、2,4−Ｄ、ブチレート、ジカンバ、ブロモキシニル、
トリジファン、イソプロチウロン、クロロトルロン、ト
リアレート、ジフルフェニカン、ジクロホップメチル、
ジフェンゾコート、イマザメタベンズ−メチル、アイオ
キシニル、メタベンズチアズロン、フルロキシピル、ク
ロルスルフロンおよびＮ−［（4,6−ジ（ジフルオロメ
トキシ）ピリミジン−２−イル）アミノカルボニル］−
２−メトキシカルボニルベンゼンスルホンアミドなどが
挙げられる。またこの他にも米国特許第4,668,277号記
載のＮ−［（4,6−ジメトキシピリミジン−２−イル）
アミノカルボニル］−３−クロロ−４−メトキシカルボ
ニル−１−メチルピラゾール−５−スルホンアミドある
いはＮ−［（4,6−ジメトキシピリミジン−２−イル）
アミノカルボニル］−３−ブロモ−４−メトキシカルボ
ニル−１−メチルピラゾール−５−スルホンアミド、特
開昭62-223180号公報記載のＮ−［（4,6−ジメトキシピ
リジン−２−イル）アミノカルボニル］−３−ジメチル
アミノカルボニルピリジン−２−スルホンアミドなどと
混合施用してもよい。その施用薬量は適用場面、施用時
期、施用方法、栽培作物等により差異はあるが一般には
有効成分量としてヘクタール当たり0.001〜10kg程度が
適当である。 In using the compound of the present invention as an agricultural or horticultural herbicide, a suitable carrier such as clay, talc, or the like is generally used.
Solid carriers such as bentonite and diatomaceous earth or water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate) ), Vinegar amides (dimethylformamide, etc.), and can be used in admixture. If desired, emulsifiers, dispersants, suspending agents, penetrants, spreading agents, stabilizers, etc. can be added. It can be put to practical use in any form such as liquid, emulsion, wettable powder, powder, granule, flowable and the like. If necessary, it may be mixed with other kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like during preparation or spraying. Examples of the types of herbicides to be mixed include, for example, Farm Chemicals H.
and book), 73rd edition (1987). Some of them are atrazine, cyanazine, arachlor, metolachlor, EPT
C, 2,4-D, butyrate, dicamba, bromoxynil,
Tridiphan, isoprothiuron, chlorotoluron, trilate, diflufenican, diclohop-methyl,
Difenzoquat, imazametabenz-methyl, ioxynil, metabenzthiazulone, fluoroxypyr, chlorsulfuron and N-[(4,6-di (difluoromethoxy) pyrimidin-2-yl) aminocarbonyl]-
2-methoxycarbonylbenzenesulfonamide and the like. In addition, N-[(4,6-dimethoxypyrimidin-2-yl) described in U.S. Pat. No. 4,668,277.
Aminocarbonyl] -3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide or N-[(4,6-dimethoxypyrimidin-2-yl)
Aminocarbonyl] -3-bromo-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide, N-[(4,6-dimethoxypyridin-2-yl) aminocarbonyl described in JP-A-62-223180 ] -3-dimethylaminocarbonylpyridine-2-sulfonamide. The amount of the applied medicine varies depending on the application scene, application time, application method, cultivated crops and the like, but generally the amount of the effective ingredient is about 0.001 to 10 kg per hectare.
つぎに本発明化合物を有効成分とする除草剤の配合例
を示すがこれらのみに限定されるものではない。なお、
以下の配合例において「部」は重量部を意味する。Next, formulation examples of the herbicide containing the compound of the present invention as an active ingredient are shown, but the invention is not limited thereto. In addition,
In the following formulation examples, “parts” means parts by weight.
配合例１ 水和剤 本発明化合物No.1 ……60部 ジークライトPFP ……33部 （カオリン系クレー：ジークライト工業（株）商品名） ソルポール5039 ……５部 （非イオン系界面活性剤とアニオン性界面活性剤との混
合物：東邦化学工業（株）商品名） カープレックス（固結防止剤） ……２部 （ホワイトカーボン：塩野義製薬（株）商品名） 以上を均一に混合粉砕して水和剤とする。Formulation Example 1 Water-dispersible compound of the present invention No. 1 60 parts Siglite PFP 33 parts (Kaolin-based clay: trade name of Siglite Industry Co., Ltd.) Solpol 5039 5 parts (Non-ionic surfactant) Mixture of phenol and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd. Carplex (anti-caking agent) 2 parts (white carbon: trade name of Shionogi & Co., Ltd.) To obtain a wettable powder.
配合例２ 乳剤 本発明化合物No.1 ……1.5部 キシレン ……78.5部 N,N−ジメチルホルムアミド ……15部 ソルポール2680 ……５部 （非イオン系界面活性剤とアニオン性界面活性剤との混
合物：東邦化学工業（株）商品名） 以上を均一に混合して乳剤とする。Formulation Example 2 Emulsion Compound No. 1 of the present invention 1.5 parts Xylene 78.5 parts N, N-dimethylformamide 15 parts Solpol 2680 5 parts (A mixture of a nonionic surfactant and an anionic surfactant Mixture: trade name of Toho Chemical Industry Co., Ltd.) The above are mixed uniformly to form an emulsion.
配合例３ フロアブル剤 本発明化合物No.1 ……40部 アグリゾールＢ−710 ……10部 （非イオン性界面活性剤：花王（株）商品名） ルノックス1000C ……0.5部 （陰イオン界面活性剤：東邦化学工業（株）商品名） １％ロドポール水 ……20部 （増粘剤：ローン・プーラン社商品名） 水 ……29.5部 以上を均一に混合して、フロアブル剤とする。Formulation Example 3 Flowable agent Compound of the present invention No. 1 40 parts Agrisol B-710 10 parts (Nonionic surfactant: trade name of Kao Corporation) Lunox 1000C 0.5 parts (Anionic surfactant) : Toho Chemical Industry Co., Ltd. 1% Rhodopol water 20 parts (Thickener: Lorn Poulin Co., Ltd.) Water 29.5 parts The above are mixed uniformly to form a flowable agent.
配合例４ 液剤 本発明化合物No.1のナトリウム塩 ……30部 ニッポール ……10部 （非イオン性界面活性剤：日産化学工業（株）商品名） 水 ……60部 以上を均一に混合して、液剤とする。Formulation Example 4 Liquid Formulation Sodium salt of Compound No. 1 of the present invention 30 parts Nippol 10 parts (Nonionic surfactant: Nissan Chemical Industry Co., Ltd.) Water 60 parts Into a liquid.
配合例５ 液剤 本発明化合物No.1のカリウム塩 ……30部 ニッポール ……10部 （非イオン性界面活性剤：日産化学工業（株）商品名） 水 ……60部 以上を均一に混合して、液剤とする。Formulation Example 5 Solution Potassium salt of Compound No. 1 of the present invention: 30 parts Nippol: 10 parts (Nonionic surfactant: Nissan Chemical Industries, Ltd.) Water: 60 parts Into a liquid.
配合例６ 液剤 本発明化合物No.1のカルシウム塩 ……30部 ニッポール ……10部 （非イオン性界面活性剤：日産化学工業（株）商品名） 水 ……60部 以上を均一に混合して、液剤とする。Formulation Example 6 Liquid Formulation Calcium salt of Compound No. 1 of the present invention 30 parts Nippol 10 parts (Nonionic surfactant: Nissan Chemical Industry Co., Ltd.) Water 60 parts Into a liquid.
配合例７ 液剤 本発明化合物No.1のイソプロピルアミン塩 ……10部 ソルポールＷ−150 ……10部 （非イオン性界面活性剤：東邦化学工業（株）商品名） 水 ……80部 以上を均一に混合して、液剤とする。Formulation Example 7 Liquid agent Isopropylamine salt of compound No. 1 of the present invention 10 parts Solpol W-150 10 parts (nonionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) Water 80 parts Mix uniformly to form a liquid.
使用に際しては上記水和剤、乳剤、フロアブル剤、液
剤を水で50〜1000倍に希釈して、有効成分が１ヘクター
ル当たり0.001〜5kgになるように散布する。For use, the above water-dispersible powder, emulsion, flowable and liquid preparation are diluted 50 to 1000 times with water and dispersed so that the active ingredient becomes 0.001 to 5 kg per hectare.
なお、本発明化合物は、畑地、水田、果樹園などの農
園芸以外に運動場、空地、線路端など非農耕地における
各種雑草の防除にも適用することができ、その施用薬量
は適用場面、施用時期、対象草種、栽培作物等により差
異はあるが一般には１ヘクタール当たり0.001〜5kg程度
になるように散布するのが適当である。In addition, the compound of the present invention can be applied to the control of various weeds in non-agricultural lands such as athletic fields, open spaces, track ends in addition to agricultural and horticultural fields such as fields, paddy fields, orchards, Although there are differences depending on the application time, target grass species, cultivated crops, etc., it is generally appropriate to spray so that the amount becomes about 0.001 to 5 kg per hectare.
次に本発明化合物の除草効果について、具体的に試験
例を挙げて説明する。Next, the herbicidal effect of the compound of the present invention will be specifically described with reference to test examples.
試験例−１ 土壌処理による除草効果試験 縦15cm,横22cm,深さ6cmのプラスチック製箱に殺菌し
た洪積土壌を入れ，ノビエ、エノコログサ、オヒシバ、
メヒシバ、オオクサキビ、イチビ、イヌビユ、イヌタ
デ、トーモロコシを播種し，更にキイロハマスゲ塊茎を
置床し、1.5cm覆土した後有効成分量が所定の割合とな
るように土壌表面へ均一に散布した。散布の際の薬液
は、前記配合例等に準じて適宜調整された水和剤、乳
剤、液剤またはフロアブル剤を水で希釈して小型スプレ
ーで全面に散布した。薬液散布３週間後に各種雑草に対
する除草効果を以下の判定基準に従い調査した。結果を
第９表に示す。化合物番号は第２表の化合物番号と同じ
である。Test Example-1 Herbicidal effect test by soil treatment Put a sterilized flood soil in a plastic box of 15 cm in length, 22 cm in width and 6 cm in depth, and add nobie, enokorogosa, ohishiba,
The crabgrass, Oosakakibi, Ichibiki, Inubiyu, Inutake, and corn were sowed, and the yellow tuber tuber was laid on the ground, covered with 1.5 cm of soil, and then uniformly spread on the soil surface so that the amount of the active ingredient became a predetermined ratio. The chemical solution at the time of spraying was prepared by diluting a wettable powder, an emulsion, a liquid formulation, or a flowable formulation appropriately adjusted according to the above-mentioned formulation examples and the like with water and spraying the whole surface with a small spray. Three weeks after spraying the chemical, the herbicidal effect on various weeds was examined according to the following criteria. The results are shown in Table 9. The compound numbers are the same as the compound numbers in Table 2.
判定基準 ５……殺草率 90％以上（ほとんど完全枯死） ４……殺草率 70〜90％ ３……殺草率 40〜70％ ２……殺草率 20〜40％ １……殺草率 5〜20％ ０……殺草率 5％未満（ほとんど効力なし） ただし，上記の殺草率は，薬剤処理区の地上部生草重
および無処理区の地上部生草重を測定して下記の式によ
り求めたものである。Judgment criteria 5: Herbicidal rate 90% or more (almost completely dead) 4: Herbicidal rate 70-90% 3: Herbicidal rate 40-70% 2: Herbicidal rate 20-40% 1: Herbicidal rate 5-20 % 0: Herbicidal rate is less than 5% (almost no effect) However, the above-mentioned herbicidal rate is calculated by the following formula by measuring the above-ground fresh grass weight in the chemical treatment area and the above-ground fresh grass weight in the untreated area. It is a thing.
試験例−２ 茎葉処理による除草効果試験１ 縦15cm,横22cm.深さ6cmのプラスチック製箱に殺菌し
た洪積土壌を入れ，ノビエ、エノコログサ、オヒシバ、
メヒシバ、オオクサキビ、オナモミ、イチビ、イヌビ
ユ、イヌタデ、トーモロコシの種子をそれぞれスポット
状に播腫し、更にキイロハマスゲ塊茎を置床し、約1.5c
m覆土した。各種植物が２〜３葉期に達したとき，有効
成分量が所定の割合となるように茎葉部へ均一に散布し
た。 Test Example-2 Test of herbicidal effect by foliage treatment 1 Put sterilized flooded soil into a plastic box of 15 cm in length, 22 cm in width and 6 cm in depth, and add nobie, enokorogosa, ohishiba,
Seeds of seeds of crabgrass, crispa, firgrass, ibis, inubuyu, inutake, and corn are spotted in spots, and a tuber of yellow croaker is placed on the tuber for about 1.5c.
m Covered soil. When the various plants reached the 2-3 leaf stage, they were evenly sprayed on the foliage so that the amount of the active ingredient became a predetermined ratio.
散布の際の約液は、前記配合例の水和剤、乳剤、液剤
またはフロアブル剤を水で希釈して小型スプレーで各種
雑草および作物の茎葉部の全面に散布した。薬液散布２
週間後に各種雑草およびトウモロコシに対する除草効果
を試験例−１の判定基準に従い，調査した。結果を第10
表に示す。化合物番号は第２表の化合物番号と同じであ
る。About the solution at the time of spraying, the wettable powder, emulsion, solution or flowable of the above-mentioned formulation example was diluted with water and sprayed with a small spray over the entire foliage of various weeds and crops. Chemical spraying 2
After a week, the herbicidal effect on various weeds and corn was investigated in accordance with the criteria of Test Example-1. Result 10
It is shown in the table. The compound numbers are the same as the compound numbers in Table 2.
試験例−３ 茎葉処理による除草効果試験２ 縦15cm,横22cm,深さ6cmのプラスチック製箱に殺菌し
た洪積土壌を入れ，オオイヌノフグリ、ハコベ、アエム
グラ、コシカギク、ハルタデ、ヒメオドリコソウ、イヌ
ホーズキ、コムギの種子をそれぞれスポット状に播腫
し、約1.5cm覆土した。各種植物が２〜３葉期に達した
とき，有効成分量が所定の割合となるように茎葉部へ均
一に散布した。Test Example-3 Test of herbicidal effect by foliage treatment 2 Put sterilized flooded soil in a plastic box of 15 cm in length, 22 cm in width and 6 cm in depth. Were seeded in spots and covered with soil of about 1.5 cm. When the various plants reached the 2-3 leaf stage, they were evenly sprayed on the foliage so that the amount of the active ingredient became a predetermined ratio.
散布の際の薬液は、前記配合例の水和剤、乳剤、液剤
またはフロアブル剤を水で希釈して小型スプレーで各種
雑草およびコムギ部の全面に散布した。薬液散布２週間
後に各種雑草およびコムギに対する除草効果を試験例−
１の判定基準に従い調査した。結果を第10表に示す。化
合物番号は、第２表の化合物番号と同じである。The chemical solution at the time of spraying was prepared by diluting the wettable powder, emulsion, solution or flowable agent of the above-mentioned formulation example with water and spraying it over the entire surface of various weeds and wheat with a small spray. Test Example-Herbicidal effect on various weeds and wheat 2 weeks after spraying the chemical
Investigation was performed according to the criteria of 1. The results are shown in Table 10. The compound numbers are the same as the compound numbers in Table 2.
第９表，第10表中の対照化合物は下記のとおりであ
る。 The control compounds in Tables 9 and 10 are as follows.
第11表中の対照化合物は下記のとおりである。 The control compounds in Table 11 are as follows.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０７Ｄ 409/14 Ｃ０７Ｄ 409/14 411/12 411/12 411/14 411/14 (72)発明者 鈴木 宏一 埼玉県南埼玉郡白岡町大字白岡1470 日 産化学工業株式会社生物科学研究所内 (72)発明者 縄巻 勤 埼玉県南埼玉郡白岡町大字白岡1470 日 産化学工業株式会社生物科学研究所内 (72)発明者 渡辺 重臣 埼玉県南埼玉郡白岡町大字白岡1470 日 産化学工業株式会社生物科学研究所内 審査官 佐野 整博 (56)参考文献 特開 昭50−126830（ＪＰ，Ａ) 特開 昭55−33454（ＪＰ，Ａ) 特開 昭55−113706（ＪＰ，Ａ) 特開 昭59−181259（ＪＰ，Ａ) 特開 昭62−53971（ＪＰ，Ａ) 特開 昭63−122673（ＪＰ，Ａ)──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 6 Identification code FI C07D 409/14 C07D 409/14 411/12 411/12 411/14 411/14 (72) Inventor Koichi Suzuki Minami Saitama-gun, Saitama 1470 Okamachi Shirooka, Nissan Chemical Industry Co., Ltd.Biological Science Research Laboratory (72) Inventor Tsutomu Nawamaki 1470 Shirookamachi Shirookamachi, Minami Saitama-gun, Saitama Prefecture Nissan Chemical Industry Co., Ltd. 1470 Shiraoka, Shiraoka-cho, Saitama-gun Niisan Chemical Industry Co., Ltd. Biological Science Research Laboratory Examiner Norihiro Sano (56) References JP-A-50-126830 (JP, A) JP-A-55-33454 (JP, A) JP-A-55-113706 (JP, A) JP-A-59-181259 (JP, A) JP-A-62-53971 (JP, A) JP-A-63-122673 (JP, A)
Claims (5)
数２〜４のアルケニル基または炭素原子数２〜４のアル
キニル基を表す。 Ｂは水素原子、炭素原子数１〜３のアルキル基、ハロゲ
ン原子、炭素原子数１〜３のハロアルキル基、炭素原子
数１〜３のアルコキシ基、炭素原子数１〜３のアルキル
チオ基、炭素原子数２〜４のアルコキシアルキル基、炭
素原子数２〜４のアルキルチオアルキル基または炭素原
子数２〜４のアルコキシカルボニル基を表す。 Ｘは炭素原子数１〜６のアルキル基、炭素原子数１〜６
のアルコキシ基、ハロゲン原子、ニトロ基、シアノ基、
炭素原子数１〜６のハロアルキル基、炭素原子数２〜６
のアルコキシアルキル基、炭素原子数２〜６のアルキル
カルボニル基、炭素原子数２〜６のアルコキシカルボニ
ル基、互いに独立して水素または炭素原子数１〜６のア
ルキル基により置換されているアミノカルボニル基、炭
素原子数１〜６のハロアルコキシ基、炭素原子数１〜６
のアルキルチオ基または炭素原子数２〜６のアルキルチ
オアルキル基を表す。 ＹはOR1基〔但し、R1は炭素原子数３〜８のシクロアル
キル基、炭素原子数４〜８のシクロアルキルアルキル
基、炭素原子数３〜６のアルケニル基、炭素原子数２〜
６のアルキニル基、炭素原子数１〜６のハロアルキル
基、炭素原子数３〜８のハロシクロアルキルアルキル
基、炭素原子数３〜６のハロアルケニル基、炭素原子数
２〜６のハロアルキニル基、炭素原子数２〜６のニトロ
アルキル基または、炭素原子数１〜３のアルキル基、ハ
ロゲン原子、ニトロ基もしくは炭素原子数１〜３のアル
コキシ基により置換されていてもよいフェニル基を表
す。〕、 Ｏ−Ｌ−Ｏ−Ｒ基〔但し、Ｌは炭素原子数１〜３のアル
キル基で置換されていてもよい炭素原子数１〜６のアル
キレン基を表す。Ｒは炭素原子数１〜４のアルキル基を
表す。〕、 Ｏ−Ｌ−Ｏ−R1基〔但し、ＬおよびR1は前記と同様の意
味を表す。〕、 Ｏ−Ｌ−OH基〔但し、Ｌは前記と同様の意味を表
す。〕、 Ｏ−Ｌ−Ｏ−Ｌ−Ｏ−R2基〔但し、Ｌは前記と同様の意
味を表す。R2は水素原子、炭素原子数１〜６のアルキル
基または、炭素原子数１〜３のアルキル基、ハロゲン原
子、ニトロ基もしくは炭素原子数１〜３のアルコキシ基
により置換されていてもよいフェニル基を表す。〕、 Ｏ−Ｌ−R3基〔但し、Ｌは前記と同様の意味を表す。R3
は炭素原子数１〜３のアルキル基、ハロゲン原子、ニト
ロ基もしくは炭素原子数１〜３のアルコキシ基により置
換されていてもよいフェニル基を表す。〕、 Ｏ−Ｍ基〔但し、Ｍは２個以内のイオウ原子あるいは酸
素原子を含み１〜４個の炭素原子と結合することによっ
て形成される員数３〜６の脂環式残基を表す。〕、 Ｏ−Ｌ−Ｍ基〔但し、ＬおよびＭは前記と同様の意味を
表す。〕、 Ｏ−Ｌ−NR4R5〔但し、Ｌは前記と同様の意味を表す。R
4およびR5は互いに独立して水素原子または炭素原子数
１〜６のアルキル基を表す。R4とR5は環を形成してもよ
い。〕、 Ｏ−Ｌ−COOR4基〔但し、ＬおよびR4は前記と同様の意
味を表す。〕、 Ｏ−CH＝CH−COOR4基〔但し、R4は前記と同様の意味を
表す。〕、 Ｏ−Ｌ−CN基〔但し、Ｌは前記と同様の意味を表
す。〕、 Ｏ−Ｌ−Ｃ（Ｏ）−R2基〔但し、ＬおよびR2は前記と同
様の意味を表す。〕、 Ｏ−Ｌ−S(O)n-R4基〔但し、ＬおよびR4は前記と同様の
意味を表す。ｎは０〜２の整数を表す。〕、 Ｏ−COOR4基〔但し、R4は前記と同様の意味を表
す。〕、 Ｏ−CONR4R5基〔但し、R4およびR5は前記と同様の意味
を表す。〕 OP(O)(OR4)2基〔但し、R4は前記と同様の意味を表
す。〕、 S(O)nR1基〔但し、R1およびｎは前記と同様の意味を表
す。〕または S(O)n−Ｌ−Ｏ−R1基〔但し、Ｌ、R1およびｎは前記と
同様の意味を表す。〕を表す。 Ｚはハロゲン原子、ニトロ基、炭素原子数１〜３のアル
コキシ基、トリフルオロメチル基、トリフルオロメトキ
シ基、シアノ基またはS(O)nR6基〔但し、ｎは前記と同
様の意味を表す。R6は炭素原子数１〜３のアルキル基ま
たは炭素原子数１〜３のハロアルキル基を表す。〕を表
す。 Ｖは水素原子、ハロゲン原子、炭素原子数１〜４のアル
キル基または炭素原子数１〜４のアルコキシ基を表す。 Ｗは水素原子、ハロゲン原子、炭素原子数１〜４のアル
キル基、炭素原子数１〜４のハロアルキル基、炭素原子
数１〜４のアルコキシ基、炭素原子数２〜６のアルコキ
シアルキル基、炭素原子数２〜５のアルコキシカルボニ
ル基、炭素原子数１〜３のハロアルコキシ基、ニトロ
基、シアノ基またはS(O)nR6〔但し、ｎおよびR6は前記
と同様の意味を表す。〕を表す。 Ｑは水素原子、ハロゲン原子で置換されていてもよい炭
素原子数１〜６のアルキル基、ハロゲン原子で置換され
ていてもよい炭素原子数１〜６のアルケニル基、ハロゲ
ン原子で置換されていてもよい炭素原子数１〜６のアル
キニル基、シアノメチル基、 −Ｃ（Ｏ）−R7基〔但し、R7は炭素原子数１〜６のアル
キル基、炭素原子数１〜６のアルケニル基、炭素原子数
１〜６のアルキニル基、炭素原子数１〜６のハロアルキ
ル基、炭素原子数１〜６のハロアルケニル基、炭素原子
数１〜６のハロアルキニル基、ハロゲン原子、ニトロ基
もしくはトルフルオロメチル基から選ばれた同一もしく
は相異なる置換基で置換されていてもよいフェニル基、
炭素原子数１〜６のアルキル基、炭素原子数１〜６のア
ルコキシ基または水酸基を表す。〕、 −S(O)2R7基〔但し、R7は前記と同様の意味を表
す。〕、 −P(O)(OR7)2基〔但し、R7は前記と同様の意味を表
す。〕、 −Ｌ−Ｃ（Ｏ）−R7基〔但し、ＬおよびR7は前記と同様
の意味を表す。〕 −Ｌ−Ｃ（Ｏ）−Ｎ（R8）（R9）〔但し、Ｌは前記と同
様の意味を表す。R8およびR9は互いに独立して水素原子
または炭素原子数１〜６のアルキル基を表す。〕 −Ｌ−R10基〔但し、Ｌは前記と同様の意味を表す。R10
はハロゲン原子、ニトロ基もしくはトリフルオロメチル
基から選ばれた同一もしくは相異なる置換基で置換され
ていてもよいフェニル基、炭素原子数１〜６のアルキル
基、炭素原子数１〜６のアルコキシ基または水酸基を表
す。〕、 −Ｌ−Ｎ（R8）（R9）基〔但し、Ｌ、R8およびR9は前記
と同様の意味を表す。〕、 −Ｌ−OR11基〔但し、Ｌは前記と同様の意味を表す。R
11は水素原子、炭素原子数１〜６のアルキル基または炭
素原子数１〜６のアルケニル基を表す。〕、 −Ｌ−OC(O)R12基〔但し、Ｌは前記と同様の意味を表
す。R12は炭素原子数１〜６のアルキル基または炭素原
子数１〜６のアルコキシ基を表す。〕、 −Ｌ−S(O)nR11基〔但し、Ｌ、ｎおよびR11は前記と同
様の意味を表す。〕、 −Ｌ−SC(O)R8基〔但し、ＬおよびR8は前記と同様の意
味を表す。〕、または 〔但し、L1およびL2は互いに独立してメチレン、酸素原
子またはイオウ原子を表す。R12は水素原子または炭素
原子数１〜３のアルキル基を表す。ｍは２または３を表
す。〕 を表す。〕 で表されるピラゾール誘導体およびその塩。1. The compound of the general formula (I) [In the formula, A represents an alkyl group having 1 to 3 carbon atoms, an alkenyl group having 2 to 4 carbon atoms or an alkynyl group having 2 to 4 carbon atoms. B is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a halogen atom, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, an alkylthio group having 1 to 3 carbon atoms, a carbon atom Represents an alkoxyalkyl group having 2 to 4 carbon atoms, an alkylthioalkyl group having 2 to 4 carbon atoms or an alkoxycarbonyl group having 2 to 4 carbon atoms. X is an alkyl group having 1 to 6 carbon atoms, 1 to 6 carbon atoms
An alkoxy group, a halogen atom, a nitro group, a cyano group,
Haloalkyl group having 1 to 6 carbon atoms, 2 to 6 carbon atoms
An alkoxycarbonyl group, an alkylcarbonyl group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, an aminocarbonyl group independently substituted by hydrogen or an alkyl group having 1 to 6 carbon atoms A haloalkoxy group having 1 to 6 carbon atoms, 1 to 6 carbon atoms
Or an alkylthioalkyl group having 2 to 6 carbon atoms. Y is an OR 1 group, provided that R 1 is a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkylalkyl group having 4 to 8 carbon atoms, an alkenyl group having 3 to 6 carbon atoms,
6 alkynyl groups, haloalkyl groups having 1 to 6 carbon atoms, halocycloalkylalkyl groups having 3 to 8 carbon atoms, haloalkenyl groups having 3 to 6 carbon atoms, haloalkynyl groups having 2 to 6 carbon atoms, Represents a nitroalkyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 3 carbon atoms, a halogen atom, a nitro group, or a phenyl group which may be substituted by an alkoxy group having 1 to 3 carbon atoms. ], An OLOR group [where L represents an alkylene group having 1 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 3 carbon atoms. R represents an alkyl group having 1 to 4 carbon atoms. ], An O-L-O-R 1 group, wherein L and R 1 have the same meanings as described above. ], An O-L-OH group wherein L represents the same meaning as described above. ], O-OLOLOR 2 group, wherein L represents the same meaning as described above. R 2 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 3 carbon atoms, a halogen atom, a nitro group or a phenyl which may be substituted by an alkoxy group having 1 to 3 carbon atoms. Represents a group. ], O-L-R 3 groups, wherein L represents the same meaning as described above. R 3
Represents a phenyl group which may be substituted by an alkyl group having 1 to 3 carbon atoms, a halogen atom, a nitro group or an alkoxy group having 1 to 3 carbon atoms. ], An O-M group [where M represents an alicyclic residue having 3 to 6 members formed by bonding to 1 to 4 carbon atoms containing up to 2 sulfur atoms or oxygen atoms. ], An OLM group [where L and M represent the same meaning as described above.] ], O-L-NR 4 R 5 [where, L is the same meanings as defined above. R
4 and R 5 independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 4 and R 5 may form a ring. ], An OL-COOR 4 group [where L and R 4 represent the same meaning as described above.] ], O-CH = CH-COOR 4 group [where R 4 represents the same meaning as described above.] ], An O-L-CN group wherein L represents the same meaning as described above. ], O-L-C (O ) -R 2 group [where, L and R 2 have the same meanings as defined above. ], O-LS (O) n -R 4 group [where L and R 4 represent the same meaning as described above.] n represents the integer of 0-2. ], O-COOR 4 group [where R 4 represents the same meaning as described above.] ], O-CONR 4 R 5 group [where, R 4 and R 5 have the same meanings as defined above. ] OP (O) (OR 4 ) 2 groups, provided that R 4 has the same meaning as described above. ], S (O) n R 1 group [where R 1 and n represent the same meaning as described above.] ] Or S (O) n -L—O—R 1 group, wherein L, R 1 and n represent the same meaning as described above. ]. Z is a halogen atom, a nitro group, an alkoxy group having 1 to 3 carbon atoms, a trifluoromethyl group, a trifluoromethoxy group, a cyano group or an S (O) n R 6 group (where n has the same meaning as described above) Represent. R 6 represents an alkyl group having 1 to 3 carbon atoms or a haloalkyl group having 1 to 3 carbon atoms. ]. V represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. W represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, An alkoxycarbonyl group having 2 to 5 atoms, a haloalkoxy group having 1 to 3 carbon atoms, a nitro group, a cyano group or S (O) n R 6 [where n and R 6 represent the same meaning as described above. ]. Q represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be substituted by a halogen atom, an alkenyl group having 1 to 6 carbon atoms which may be substituted by a halogen atom, A alkynyl group having 1 to 6 carbon atoms, a cyanomethyl group, a —C (O) —R 7 group [where R 7 is an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, An alkynyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a haloalkenyl group having 1 to 6 carbon atoms, a haloalkynyl group having 1 to 6 carbon atoms, a halogen atom, a nitro group or trifluoro. A phenyl group which may be substituted with the same or different substituent (s) selected from a methyl group,
Represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or a hydroxyl group. ], -S (O) 2 R 7 group [where, R 7 have the same meanings as defined above. ], -P (O) (OR 7 ) 2 groups, wherein R 7 has the same meaning as described above. ], -L-C (O) -R 7 group [where, L and R 7 have the same meanings as defined above. -LC (O) -N (R 8 ) (R 9 ) wherein L represents the same meaning as described above. R 8 and R 9 independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ] -LR 10 groups [where L represents the same meaning as described above.] R 10
Is a phenyl group which may be substituted by the same or different substituents selected from a halogen atom, a nitro group or a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms Or represents a hydroxyl group. ], -L-N (R 8 ) (R 9 ) group [however, L, R 8 and R 9 represent the same meaning as described above. ], -L-OR 11 group [where, L is the same meanings as defined above. R
11 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkenyl group having 1 to 6 carbon atoms. ], -L-OC (O) R 12 group [where, L is the same meanings as defined above. R 12 represents an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. ], -L-S (O) n R 11 group [where, L, n and R 11 have the same meanings as defined above. ], -L-SC (O) R 8 group [where, L and R 8 have the same meanings as defined above. ], Or [However, L1 and L2 independently represent a methylene, an oxygen atom or a sulfur atom. R 12 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. m represents 2 or 3. ] Is represented. ] The pyrazole derivative represented by these, and its salt.
上を有効成分として含有することを特徴とする選択性除
草剤。2. A selective herbicide comprising one or more of the compounds according to claim 1 as an active ingredient.
Ｚ、Ｖ、ＷおよびＱが以下から選ばれるピラゾール誘導
体 A:Me,Et,n−Pr,i−Pr,CH2CH＝CH2，CH2C≡CH; B:H,Me,Et,n−Pr,i−Pr,Cl,Br,CH2Cl，CF3,OMe,OEt,OPr
−i,SMe,CH2OMe，CH2SMe，CO2Me，CO2Et； X:Me,Et,n−Pr,i−Pr,n−Bu,i−Bu,s−Bu,t−Bu,OMe,OE
t,OPr−n,OPr−i,OBu−n,OBu−i,OBu−s,OBu−t,F,Cl,B
r,I,NO2,CN,CH2F，CHF2，CF3，CH2CF3，CH2Cl，CCl3,CH
ClMe,CH2CH2Cl，CHClCH2Cl，CH2Br,CHBrMe,CH2CH2Br，C
H2OMe，CH2OEt，CH2OPr−n,CH2OPr−i,CH2OBu−n,CH2OB
u−i,CH2OBu−s,CH2OBu−t,CHMeOMe,CHMeOEt,CHMeOPr−
n,CHMeOPr−i,CHMeOBu−n,CHMeOBu−i,CHMeOBu−s,CHMe
OBu−t,CH2CH2OMe，CH2CH2OEt，CH2CH2OPr−i,Ac,COEt,
COPr−n,COPr−i,COOMe,COOEt,COOPr−i,CONHMe,CONHE
t,CONMe2，CONEt2,CONEtMe,OCHF2，OCF3，OCH2CF3,SMe,
SEt,CH2SMe，CH2SEt,CHMeSMe,CHMeSEt; Y:O−シクロペンチル,O−シクロヘキシル、Ｏ−シクロ
プロピル、OCH2−シクロプロピル，OCH2-2,2−ジメチル
シクロプロピル，OCH2−シクロペンチル、OCH2−シクロ
ヘキシル，OCH2CH＝CH2,OCHMeCH＝CH2，OCMe2CH＝CH2，
OCH2CMe＝CH2，OCH2CH＝CHMe,OCH2CH＝CMe2，OCH2C≡C
H,OCHMeC≡CH,OCMe2C≡CH,OCH2C≡CMe,OCH2CH2F，OCH2C
HF2，OCH2CF3，OCH2CH2Cl，OCHMeCH2Cl，OCH2CCl3，OCH
2CH2CH2Cl，OCH2CH2Br，OCH2-2,2−ジクロロシクロプロ
ピル，OCH2CCl＝CH2，OCH2CH2CH＝CH2，OCH2CCl＝CHCl,
OCH2CH2NO2,OPh,OPh-Me−2,OPh-Cl−4,OPh-NO2−4,OCH2
CH2OMe，OCH2CH2OEt，OCH2CH2OPr−n,OCH2CH2OPr−i,OC
H2CH2OBu−n,OCH2CH2OBu−i,OCH2CH2OBu−s,OCH2CH2OBu
−t,OCHMeCH2OMe，OCH2CH2OPh，OCH2CH2OCH2CH2OMe，OC
H2CH2OH，OCH2CH2OCHMeCH2OMe，OCH2Ph,OCHMePh,OCH2Ph
−４−Me,OCH2Ph−４−Cl,OCH2CH2Ph,O−３−テトラヒ
ドロフラニル,O−２−テトラヒドロピラニル,O−４−テ
トラヒドロピラニル,O−３−テトラヒドロピラニル,O−
３−テトラヒドロチエニル，OCH2エポキシエチル，OCH2
−３−テトラヒドロフラニル，OCH2−２−テトラヒドロ
フラニル，OCH2−２−テトラヒドロピラニル，OCH2−３
−テトラヒドロチオピラニル，OCH2CH2NH2，OCH2CH2NHM
e，OCH2CH2NMe2，OCH2CH2NEt2，OCH2CH2N(CH2)5，OCH2C
OOMe，OCH2COOEt，OCH2COOPr−n,OCH2COOPr−i,OCH2COO
Bu−t,OCHMeCOOMe,OCHMeCOOEt,OCHMeCOOPr−n,OCHMeCOO
Pr−i,OCHMeCOOBu−t,OCH2CH2CN，OCH2CN,OCHMeCN,OCH2
SMe，OCH2C(O)Ph，OCH2C(O)Me，OCH2CH2SMe，OCH2CH2SO
Me，OCH2CH2SO2Me，OCH2CH2SEt，OCH2CH2SO2Et,OCOOMe,
OCOOEt,OCOOPr−i,OCONH2,OCONHMe,OCONMe2，OP(O)(OM
e)2，OP(O)(OEt)2，SCH2−シクロプロピル，SCH2CH＝CH
2，SCH2C≡CH,SCH2CF3，SCH2CH2Cl，SCH2CCl3，SCH2-2,
2−ジクロロシクロプロピル,SPh,SCH2CH2OMe，SCH2CH2O
Et，SCH2CH2OPr−i,SCH2CH2OPh，S(O)CH2−シクロプロ
ピル，S(O)CH2CH＝CH2，S(O)CH2C≡CH,S(O)CH2CF3，S
(O)CH2CH2Cl，S(O)CH2-2,2−ジクロロシクロプロピル,S
（Ｏ）Ph,S(O)CH2CH2OMe，S(O)CH2CH2OEt，S(O)CH2CH2O
Pr−i,S(O)CH2CH2OPh，SO2CH2−シクロプロピル，SO2CH
2CH＝CH2，SO2CH2C≡CH,SO2CH2CF3，SO2CH2CH2Cl，SO2C
H2-2,2−ジクロロシクロプロピル，SO2Ph，SO2CH2CH2OM
e，SO2CH2CH2OEt，SO2CH2CH2OPr−i; Z:F,Cl,Br,I,NO2,OMe,OEt,OPr−n,OPr−i,CF3,CN,SMe,S
OMe,SO2Me，SCF3，SOCF3，SO2CF3； V:H; W:H; Q:H,Me,Et,n−Pr,i−Pr,n−Bu,i−Bu,s−Bu,t−Bu,CH2C
H2Cl，CH2CF3,CHClMe,CH2CH2Br，CHClCH2Cl，CH2CH＝CH
2，CH2CMe＝CH2，CH2CH＝CHMe,CH2C≡CH,CH2CCl＝CH2，
CH2CN，CH2Ph，CH2Ph‐Cl−2,CH2Ph‐Cl−3,CH2Ph‐Me
−2,ペンタフルオロベンジル，CH2Ph‐Me2-2,4,CH2Ph‐
Me−4,CHMePh,CHEtPh,CH2Ph‐NO2−2,CH2Ph‐CF3−3,CH
2OMe，CH2OEt，CH2OH,CHMeOH,CH2NHMe，CH2NMe2，CHMeN
Me2，CH2COPh，CH2COPh‐NO2−4,CH2COPh‐Me−4,CH2CO
Ph‐Cl−4,CH2COPh‐Me2-2,4,CH2COPh-CF3−4,CH2Ac，C
H2Et,CHMeAc,CH2CO2Me，CH2CO2Et，CH2CO2Pr−n,CH2CO2
Pr−i,CH2CO2Bu−t,CH2CO2H，CHMeCO2H，CH2CONHMe，CH
2CONMe2，CH2CONHEt，CH2CONEt2，CH2CONPr-n2，CH2OCH
2CH＝CH2，CH2OAc，CH2COEt，CH2COPr−i,CH2COBu−t,C
H2OCO2Me，CH2OCO2Et，CH2OCO2Pr−i,CH2OCO2Bu−t,CH2
SMe，CH2SEt，CH2SCH2CH＝CH2，CH2SAc，CH2SCOBu−t,C
H2SO2Me，CH2SO2Et，CH2SO2CH2CH＝CH2，CH2NHCH2CH＝C
H2，CH2NMeCH2CH＝CH2，CH2NHAc，CH2NHCOEt，CH2NHCO2
Me，CH2NHCO2Et，CH2NMeCO2Me,COPh,COPh-Me−4,COPh-N
O2−2,COPh-Cl2-2,4,Ac,COEt,COPr−n,COPr−i,COBu−
n,COBu−t,COCH2Cl，COCHCl2，COCCl3，COCF3，COCH3OM
e，COCH2OPh，COCH2CH＝CHCH3，CO2Me，CO2Et，CO2Bu−
t,CO2Pr−i,CONHMe,CONMe2,CONHEt,CONEt2，CONPr-n2,C
ON（CH2CH＝CH2）2,CONMePh,CON(CH2)4，CON(CH2)5,CO
（モルホリノ），CO2CH2Ph，CO2Ph，SO2Me，SO2Et，SO2
CH2CH＝CH2，SO2Ph，SO2Ph‐Me−4,SO2Ph‐Cl−4,SO2Ph
-(NO2)2-2,4,SO2CF3,P（＝Ｏ）（OMe）2,P（＝Ｏ）（OE
t）2,P（＝Ｏ）（OPr−ｎ）2,P（＝Ｏ）（OPr−ｉ）2,P
（＝Ｓ）（OMe）2,P（＝Ｓ）（OEt）2,P（＝Ｏ）OMeOP
h,P（＝Ｏ）（OCH2CH＝CH2）2,P（＝Ｏ）OPhOCH2CH＝CH
2． およびＱが水素原子を表すとき、以下から選ばれる金属
もしくは有機塩基からなる塩。 金属：ナトリウム，カリウム，カルシウム，リチウム，
バリウム，マグネシウム，鉄，銅，ニッケル，マンガ
ン． 有機塩基：メチルアミン，ジメチルアミン，トリメチル
アミン，エチルアミン，ジエチルアミン，トリエチルア
ミン，ノルマルプロピルアミン，ジノルマルプロピルア
ミン，イソプロピルアミン，ジイソプロピルアミン，ノ
ルマルブチルアミン，イソブチルアミン，セカンダリー
ブチルアミン，ターシャリーブチルアミン，ピペリジ
ン，ピロリジン，モルホリン，ピリジン,N,N−ジメチル
アニリン，コリン．3. The method according to claim 1, wherein A, B, X, Y,
Z, V, W and Q pyrazole is selected from the following derivatives A: Me, Et, n- Pr, i-Pr, CH 2 CH = CH 2, CH 2 C≡CH; B: H, Me, Et, n −Pr, i−Pr, Cl, Br, CH 2 Cl, CF 3 , OMe, OEt, OPr
−i, SMe, CH 2 OMe, CH 2 SMe, CO 2 Me, CO 2 Et; X: Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu , OMe, OE
t, OPr-n, OPr-i, OBu-n, OBu-i, OBu-s, OBu-t, F, Cl, B
r, I, NO 2 , CN, CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CH 2 Cl, CCl 3 , CH
ClMe, CH 2 CH 2 Cl, CHClCH 2 Cl, CH 2 Br, CHBrMe, CH 2 CH 2 Br, C
H 2 OMe, CH 2 OEt, CH 2 OPr-n, CH 2 OPr-i, CH 2 OBu-n, CH 2 OB
u-i, CH 2 OBu- s, CH 2 OBu-t, CHMeOMe, CHMeOEt, CHMeOPr-
n, CHMeOPr-i, CHMeOBu-n, CHMeOBu-i, CHMeOBu-s, CHMe
OBu-t, CH 2 CH 2 OMe, CH 2 CH 2 OEt, CH 2 CH 2 OPr-i, Ac, COEt,
COPr-n, COPr-i, COOMe, COOEt, COOPr-i, CONHMe, CONHE
t, CONMe 2 , CONEt 2 , CONEtMe, OCHF 2 , OCF 3 , OCH 2 CF 3 , SMe,
SEt, CH 2 SMe, CH 2 SEt, CHMeSMe, CHMeSEt; Y: O-cyclopentyl, O-cyclohexyl, O-cyclopropyl, OCH 2 -cyclopropyl, OCH 2 -2,2-dimethylcyclopropyl, OCH 2 -cyclopentyl , OCH 2 - cyclohexyl, OCH 2 CH = CH 2, OCHMeCH = CH 2, OCMe 2 CH = CH 2,
OCH 2 CMe = CH 2 , OCH 2 CH = CHMe, OCH 2 CH = CMe 2 , OCH 2 C≡C
H, OCHMeC≡CH, OCMe 2 C≡CH, OCH 2 C≡CMe, OCH 2 CH 2 F, OCH 2 C
HF 2 , OCH 2 CF 3 , OCH 2 CH 2 Cl, OCHMeCH 2 Cl, OCH 2 CCl 3 , OCH
2 CH 2 CH 2 Cl, OCH 2 CH 2 Br, OCH 2 -2,2-dichlorocyclopropyl, OCH 2 CCl = CH 2 , OCH 2 CH 2 CH = CH 2 , OCH 2 CCl = CHCl,
OCH 2 CH 2 NO 2, OPh , OPh-Me-2, OPh-Cl-4, OPh-NO 2 -4, OCH 2
CH 2 OMe, OCH 2 CH 2 OEt, OCH 2 CH 2 OPr-n, OCH 2 CH 2 OPr-i, OC
H 2 CH 2 OBu-n, OCH 2 CH 2 OBu-i, OCH 2 CH 2 OBu-s, OCH 2 CH 2 OBu
−t, OCHMeCH 2 OMe, OCH 2 CH 2 OPh, OCH 2 CH 2 OCH 2 CH 2 OMe, OC
H 2 CH 2 OH, OCH 2 CH 2 OCHMeCH 2 OMe, OCH 2 Ph, OCHMePh, OCH 2 Ph
-4-Me, OCH 2 Ph- 4-Cl, OCH 2 CH 2 Ph, O-3- tetrahydrofuranyl, O-2-tetrahydropyranyl, O-4-tetrahydropyranyl, O-3- tetrahydropyranyl, O-
3-tetrahydrothienyl, OCH 2 epoxyethyl, OCH 2
-3-tetrahydrofuranyl, OCH 2-2-tetrahydrofuranyl, OCH 2-2-tetrahydropyranyl, OCH 2 -3
-Tetrahydrothiopyranyl, OCH 2 CH 2 NH 2 , OCH 2 CH 2 NHM
e, OCH 2 CH 2 NMe 2 , OCH 2 CH 2 NEt 2 , OCH 2 CH 2 N (CH 2 ) 5 , OCH 2 C
OOMe, OCH 2 COOEt, OCH 2 COOPr-n, OCH 2 COOPr-i, OCH 2 COO
Bu-t, OCHMeCOOMe, OCHMeCOOEt, OCHMeCOOPr-n, OCHMeCOO
Pr-i, OCHMeCOOBu-t, OCH 2 CH 2 CN, OCH 2 CN, OCHMeCN, OCH 2
SMe, OCH 2 C (O) Ph, OCH 2 C (O) Me, OCH 2 CH 2 SMe, OCH 2 CH 2 SO
Me, OCH 2 CH 2 SO 2 Me, OCH 2 CH 2 SEt, OCH 2 CH 2 SO 2 Et, OCOOMe,
OCOOEt, OCOOPr-i, OCONH 2 , OCONHMe, OCONMe 2, OP (O) (OM
e) 2 , OP (O) (OEt) 2 , SCH 2 -cyclopropyl, SCH 2 CH = CH
2 , SCH 2 C≡CH, SCH 2 CF 3 , SCH 2 CH 2 Cl, SCH 2 CCl 3 , SCH 2 -2,
2-dichlorocyclopropyl, SPh, SCH 2 CH 2 OMe, SCH 2 CH 2 O
Et, SCH 2 CH 2 OPr-i, SCH 2 CH 2 OPh, S (O) CH 2 -cyclopropyl, S (O) CH 2 CH = CH 2 , S (O) CH 2 C≡CH, S (O ) CH 2 CF 3 , S
(O) CH 2 CH 2 Cl, S (O) CH 2 -2,2-dichlorocyclopropyl, S
(O) Ph, S (O) CH 2 CH 2 OMe, S (O) CH 2 CH 2 OEt, S (O) CH 2 CH 2 O
Pr-i, S (O) CH 2 CH 2 OPh, SO 2 CH 2 - cyclopropyl, SO 2 CH
2 CH = CH 2 , SO 2 CH 2 C≡CH, SO 2 CH 2 CF 3 , SO 2 CH 2 CH 2 Cl, SO 2 C
H 2 -2,2-dichlorocyclopropyl, SO 2 Ph, SO 2 CH 2 CH 2 OM
e, SO 2 CH 2 CH 2 OEt, SO 2 CH 2 CH 2 OPr-i; Z: F, Cl, Br, I, NO 2, OMe, OEt, OPr-n, OPr-i, CF 3, CN, SMe, S
OMe, SO 2 Me, SCF 3 , SOCF 3 , SO 2 CF 3 ; V: H; W: H; Q: H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s −Bu, t−Bu, CH 2 C
H 2 Cl, CH 2 CF 3 , CHClMe, CH 2 CH 2 Br, CHClCH 2 Cl, CH 2 CH = CH
2 , CH 2 CMe = CH 2 , CH 2 CH = CHMe, CH 2 C≡CH, CH 2 CCl = CH 2 ,
CH 2 CN, CH 2 Ph, CH 2 Ph-Cl-2, CH 2 Ph-Cl-3, CH 2 Ph-Me
−2, pentafluorobenzyl, CH 2 Ph-Me 2 -2,4, CH 2 Ph-
Me-4, CHMePh, CHEtPh, CH 2 Ph-NO 2 -2, CH 2 Ph-CF 3 -3, CH
2 OMe, CH 2 OEt, CH 2 OH, CHMeOH, CH 2 NHMe, CH 2 NMe 2 , CHMeN
Me 2, CH 2 COPh, CH 2 COPh-NO 2 -4, CH 2 COPh-Me-4, CH 2 CO
Ph-Cl-4, CH 2 COPh-Me 2 -2,4, CH 2 COPh-CF 3 -4, CH 2 Ac, C
H 2 Et, CHMeAc, CH 2 CO 2 Me, CH 2 CO 2 Et, CH 2 CO 2 Pr-n, CH 2 CO 2
Pr-i, CH 2 CO 2 Bu-t, CH 2 CO 2 H, CHMeCO 2 H, CH 2 CONHMe, CH
2 CONMe 2 , CH 2 CONHEt, CH 2 CONEt 2 , CH 2 CONPr-n 2 , CH 2 OCH
2 CH = CH 2 , CH 2 OAc, CH 2 COEt, CH 2 COPr-i, CH 2 COBu-t, C
H 2 OCO 2 Me, CH 2 OCO 2 Et, CH 2 OCO 2 Pr-i, CH 2 OCO 2 Bu-t, CH 2
SMe, CH 2 SEt, CH 2 SCH 2 CH = CH 2 , CH 2 SAc, CH 2 SCOBu−t, C
H 2 SO 2 Me, CH 2 SO 2 Et, CH 2 SO 2 CH 2 CH = CH 2 , CH 2 NHCH 2 CH = C
H 2 , CH 2 NMeCH 2 CH = CH 2 , CH 2 NHAc, CH 2 NHCOEt, CH 2 NHCO 2
Me, CH 2 NHCO 2 Et, CH 2 NMeCO 2 Me, COPh, COPh-Me-4, COPh-N
O 2 -2, COPh-Cl 2 -2,4, Ac, COEt, COPr-n, COPr-i, COBu-
n, COBu-t, COCH 2 Cl, COCHCl 2 , COCCl 3 , COCF 3 , COCH 3 OM
e, COCH 2 OPh, COCH 2 CH = CHCH 3 , CO 2 Me, CO 2 Et, CO 2 Bu−
t, CO 2 Pr-i, CONHMe, CONMe 2 , CONHEt, CONEt 2 , CONPr-n 2 , C
ON (CH 2 CH = CH 2 ) 2 , CONMePh, CON (CH 2 ) 4 , CON (CH 2 ) 5 , CO
(Morpholino), CO 2 CH 2 Ph, CO 2 Ph, SO 2 Me, SO 2 Et, SO 2
CH 2 CH = CH 2 , SO 2 Ph, SO 2 Ph-Me-4, SO 2 Ph-Cl-4, SO 2 Ph
-(NO 2 ) 2 -2,4, SO 2 CF 3 , P (= O) (OMe) 2 , P (= O) (OE
t) 2 , P (= O) (OPr-n) 2 , P (= O) (OPr-i) 2 , P
(= S) (OMe) 2 , P (= S) (OEt) 2 , P (= O) OMeOP
h, P (= O) (OCH 2 CH = CH 2 ) 2 , P (= O) OPhOCH 2 CH = CH
2 . And when Q represents a hydrogen atom, a salt comprising a metal or an organic base selected from the following. Metals: sodium, potassium, calcium, lithium,
Barium, magnesium, iron, copper, nickel, manganese. Organic base: methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, normal propylamine, dinormalpropylamine, isopropylamine, diisopropylamine, normal butylamine, isobutylamine, secondary butylamine, tertiary butylamine, piperidine, pyrrolidine, morpholine , Pyridine, N, N-dimethylaniline, choline.
Ｚ、Ｖ、ＷおよびＱが以下から選ばれるピラゾール誘導
体。 A:Me,Et,Pr−i; B:H,Me; X:Cl; Y:OCH2CH2OMe，OCH2CH2OEt，OCH2CH2OPr−i; Z:SO2Me； V:H; W:H; Q:H.4. The method according to claim 3, wherein A, B, X, Y,
A pyrazole derivative wherein Z, V, W and Q are selected from the following. A: Me, Et, Pr-i; B: H, Me; X: Cl; Y: OCH 2 CH 2 OMe, OCH 2 CH 2 OEt, OCH 2 CH 2 OPr-i; Z: SO 2 Me; V: H; W: H; Q: H.
Ｚ、Ｖ、ＷおよびＱが以下から選ばれるピラゾール誘導
体。 A:Me,Et,Pr−i; B:H; X:Cl; Y:OCH2CH2OMe； Z:SO2Me； V:H; W:H; Q:H.5. The method according to claim 4, wherein A, B, X, Y,
A pyrazole derivative wherein Z, V, W and Q are selected from the following. A: Me, Et, Pr-i; B: H; X: Cl; Y: OCH 2 CH 2 OMe; Z: SO 2 Me; V: H; W: H; Q: H.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1120983A JP2738010B2 (en) | 1988-07-15 | 1989-05-15 | Pyrazole inducers and selective herbicides |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17675888 | 1988-07-15 | ||
| JP63-176758 | 1989-02-03 | ||
| JP2603089 | 1989-02-03 | ||
| JP1-26030 | 1989-02-03 | ||
| JP1120983A JP2738010B2 (en) | 1988-07-15 | 1989-05-15 | Pyrazole inducers and selective herbicides |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26944197A Division JP2907333B2 (en) | 1988-07-15 | 1997-10-02 | Substituted benzenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02288866A JPH02288866A (en) | 1990-11-28 |
| JP2738010B2 true JP2738010B2 (en) | 1998-04-08 |
Family
ID=27285243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1120983A Expired - Fee Related JP2738010B2 (en) | 1988-07-15 | 1989-05-15 | Pyrazole inducers and selective herbicides |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2738010B2 (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4092524T (en) * | 1990-03-07 | 1992-04-23 | ||
| WO1993018031A1 (en) * | 1992-03-03 | 1993-09-16 | Idemitsu Kosan Co., Ltd. | Pyrazole derivative |
| BR9408026A (en) * | 1993-11-09 | 1996-12-17 | Idemitsu Kosan Co | Pyrazole derivatives and herbicides containing the same |
| AU6523498A (en) * | 1997-04-08 | 1998-10-30 | Nippon Soda Co., Ltd. | 4-benzoylpyrazole derivatives and herbicides |
| WO1998056766A1 (en) * | 1997-06-12 | 1998-12-17 | Nippon Soda Co., Ltd. | Benzoylpyrazole derivatives having specified substituents and herbicides |
| JP4592129B2 (en) * | 1998-07-14 | 2010-12-01 | 日本曹達株式会社 | Novel benzoic acid derivatives and process for producing the same |
| DE10235945A1 (en) * | 2002-08-06 | 2004-02-19 | Bayer Cropscience Gmbh | New 4-(3-substituted benzoyl)-pyrazol-5-one derivatives, useful as broad-spectrum, pre- and post-emergence herbicides especially for selective weed control in crops e.g. wheat, maize and rice |
| AR056889A1 (en) | 2005-12-15 | 2007-10-31 | Ishihara Sangyo Kaisha | BENZOILPIRAZOL AND HERBICIDE COMPOUNDS CONTAINING THEM |
| JP5420169B2 (en) * | 2006-12-27 | 2014-02-19 | 石原産業株式会社 | Herbicides containing benzoylpyrazole compounds |
| JP2010006798A (en) * | 2008-05-27 | 2010-01-14 | Ishihara Sangyo Kaisha Ltd | Benzoylpyrazole-based compound, method for producing the same, and herbicide containing the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5436648B2 (en) * | 1974-03-28 | 1979-11-10 | ||
| JPS6022713B2 (en) * | 1978-09-01 | 1985-06-03 | 三共株式会社 | Pyrazole derivative |
| JPS55113706A (en) * | 1979-02-02 | 1980-09-02 | Sankyo Co Ltd | Herbicide |
| JPS59181259A (en) * | 1983-03-29 | 1984-10-15 | Nippon Nohyaku Co Ltd | Pyrazole derivative, insecticide, fungicide, and herbicide |
| JPH0625133B2 (en) * | 1985-09-03 | 1994-04-06 | 日産化学工業株式会社 | Pyrazole derivative, its production method and selective herbicide |
| JPS63122673A (en) * | 1986-11-10 | 1988-05-26 | Nissan Chem Ind Ltd | Pyrazole derivative and herbicide |
-
1989
- 1989-05-15 JP JP1120983A patent/JP2738010B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02288866A (en) | 1990-11-28 |
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| LAPS | Cancellation because of no payment of annual fees |