JPS63122672A - Pyrazole derivative and selective herbicide - Google Patents
Pyrazole derivative and selective herbicideInfo
- Publication number
- JPS63122672A JPS63122672A JP26686286A JP26686286A JPS63122672A JP S63122672 A JPS63122672 A JP S63122672A JP 26686286 A JP26686286 A JP 26686286A JP 26686286 A JP26686286 A JP 26686286A JP S63122672 A JPS63122672 A JP S63122672A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- parts
- compound shown
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 29
- 239000004009 herbicide Substances 0.000 title claims abstract description 13
- 150000003217 pyrazoles Chemical class 0.000 title claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 240000008042 Zea mays Species 0.000 claims abstract description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims abstract description 10
- 241000209140 Triticum Species 0.000 claims abstract description 8
- 235000021307 Triticum Nutrition 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 9
- 235000005822 corn Nutrition 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 46
- 239000003795 chemical substances by application Substances 0.000 abstract description 15
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 10
- -1 1-substituted-5-hydroxypyrazole Chemical class 0.000 abstract description 9
- 235000010233 benzoic acid Nutrition 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 239000005711 Benzoic acid Substances 0.000 abstract description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012442 inert solvent Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 abstract 1
- 235000009973 maize Nutrition 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 25
- 239000000203 mixture Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- 239000004563 wettable powder Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000002736 nonionic surfactant Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 239000003945 anionic surfactant Substances 0.000 description 9
- 230000009969 flowable effect Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 231100000674 Phytotoxicity Toxicity 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 240000001341 Reynoutria japonica Species 0.000 description 6
- 235000018167 Reynoutria japonica Nutrition 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 5
- 240000002439 Sorghum halepense Species 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 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 5
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000003173 Drymaria cordata Species 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- 239000012669 liquid formulation Substances 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 240000008100 Brassica rapa Species 0.000 description 2
- 241001038806 Carex kobomugi Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 1
- RRFGGUXLGOVPOP-UHFFFAOYSA-N 2-chloro-3-methyl-4-methylsulfonylbenzoic acid Chemical compound CC1=C(Cl)C(C(O)=O)=CC=C1S(C)(=O)=O RRFGGUXLGOVPOP-UHFFFAOYSA-N 0.000 description 1
- QZVRXWBKQJFSLP-UHFFFAOYSA-N 2-ethyl-1h-pyrazol-3-one Chemical compound CCN1NC=CC1=O QZVRXWBKQJFSLP-UHFFFAOYSA-N 0.000 description 1
- XPNHHPXSCYDOKL-UHFFFAOYSA-N 4-benzoyl-1,2-dihydropyrazol-3-one Chemical compound N1N=CC(C(=O)C=2C=CC=CC=2)=C1O XPNHHPXSCYDOKL-UHFFFAOYSA-N 0.000 description 1
- OBTFNIOWJJRVQV-UHFFFAOYSA-N 5-ethyl-1,2-dihydropyrazol-3-one Chemical compound CCC1=CC(=O)NN1 OBTFNIOWJJRVQV-UHFFFAOYSA-N 0.000 description 1
- 241001311476 Abies veitchii Species 0.000 description 1
- 235000005637 Brassica campestris Nutrition 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 235000011292 Brassica rapa Nutrition 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- NYVBMLSJJYADGC-UHFFFAOYSA-N CC(C)N1N=CC=C1O Chemical compound CC(C)N1N=CC=C1O NYVBMLSJJYADGC-UHFFFAOYSA-N 0.000 description 1
- AYLNCWPBDCCFGV-UHFFFAOYSA-N CC1=C(C(=O)C=2C=NN(C2O)CC)C=CC(=C1C)S(=O)(=O)C Chemical compound CC1=C(C(=O)C=2C=NN(C2O)CC)C=CC(=C1C)S(=O)(=O)C AYLNCWPBDCCFGV-UHFFFAOYSA-N 0.000 description 1
- HDZGLVYIHGTDFF-UHFFFAOYSA-N CCN1N=CC(C(=O)C=2C(=C(C)C(=CC=2)S(C)(=O)=O)Cl)=C1O Chemical compound CCN1N=CC(C(=O)C=2C(=C(C)C(=CC=2)S(C)(=O)=O)Cl)=C1O HDZGLVYIHGTDFF-UHFFFAOYSA-N 0.000 description 1
- 241001244495 Carex flava Species 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 244000260524 Chrysanthemum balsamita Species 0.000 description 1
- 235000005633 Chrysanthemum balsamita Nutrition 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 244000301850 Cupressus sempervirens Species 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 241001656769 Lilium canadense Species 0.000 description 1
- 241001502129 Mullus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000277269 Oncorhynchus masou Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001076438 Oxya japonica Species 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 240000004155 Saccharum barberi Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 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
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 239000006227 byproduct Substances 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 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
- 239000002552 dosage form Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000004094 surface-active 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
- UTLZBWAGLRNNAY-UHFFFAOYSA-J thorium(4+);dicarbonate Chemical compound [Th+4].[O-]C([O-])=O.[O-]C([O-])=O UTLZBWAGLRNNAY-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規なピラゾール誘導体および該誘導体を含
有する選択性除草剤に関するものであり、特にトウモロ
コシ畑および小麦畑に繁茂する各種の雑草に対して、極
めて低薬量で殺草効果を示す優れた選択性除草剤に関す
るものである。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a new pyrazole derivative and a selective herbicide containing the derivative, and is particularly effective against various weeds growing in corn and wheat fields. On the other hand, it relates to an excellent selective herbicide that exhibits herbicidal effects at extremely low dosages.
従来、除草活性を有するピラゾール誘４体に関しては数
多（知られている。例えば特公昭５４−３６６４８号公
報、特開昭６０−５１１７５号公報等が挙げられる。Conventionally, a large number of pyrazole derivatives having herbicidal activity are known. For example, Japanese Patent Publication No. 54-36648, Japanese Patent Application Laid-Open No. 60-51175, etc. are known.
特公昭５４−３６６４８号公報に記載のピラゾール誘導
体は、主として水田用除草剤に関するものである。The pyrazole derivatives described in Japanese Patent Publication No. 54-36648 are mainly related to herbicides for paddy fields.
特開昭６０−５１１７５号公報は、本願出願人が先に出
願したものであり、トウモロコシ畑の雑草に対して除草
効果を有することが記載されている。Japanese Unexamined Patent Publication No. 60-51175 was previously filed by the applicant of the present invention, and describes that it has a herbicidal effect on weeds in corn fields.
しかしながら、従来の数多くのピラゾール誘導体の中で
極めて低薬量で特にトウモロコシ畑や小麦畑に繁茂する
各種の雑草や難防除雑草に対して、優れた殺草効果を示
す選択性除草剤は、はとんどないのが現状である。However, among the many conventional pyrazole derivatives, there are selective herbicides that exhibit excellent herbicidal effects against various weeds and difficult-to-control weeds that grow especially in corn and wheat fields at extremely low doses. The current situation is terrible.
本発明は、一般式（１）
で表されるピラゾール誘導体またはその塩ならびに該誘
導体またはその塩の１種もしくは２種以上を有効成分と
して含有する選択性除草剤に関する。The present invention relates to a pyrazole derivative represented by the general formula (1) or a salt thereof, and a selective herbicide containing one or more of the derivatives or salts thereof as active ingredients.
〔上記式中、Ｒは、炭素数２または３のアルキル基を、
Ｘは、炭素数１．２もしくは３のアルキル基またはハロ
ゲン原子を、Ｙは、水素原子、炭素数１もしくは２のア
ルキル基またはハロゲン原子を表す。〕
本発明において、Ｒとしてはエチル基、イソプロピル基
、ノルマルプロピル基が挙げられるが、エチル基および
イソプロピル基が好ましい。Ｘとしてはメチル基、エチ
ル基、イソプロピル基、ノルマルプロピル基が挙げられ
るが、特にメチル基が好ましく、ハロゲン原子としては
塩素原子が好ましい。Ｙとしては水素原子、メチル基お
よびエチル基が挙げられるが、特にメチル基が好ましく
、ハロゲン原子としては弗素原子が好ましい。[In the above formula, R is an alkyl group having 2 or 3 carbon atoms,
X represents an alkyl group having 1.2 or 3 carbon atoms or a halogen atom, and Y represents a hydrogen atom, an alkyl group having 1 or 2 carbon atoms, or a halogen atom. ] In the present invention, examples of R include ethyl group, isopropyl group, and normal propyl group, and ethyl group and isopropyl group are preferable. Examples of X include a methyl group, an ethyl group, an isopropyl group, and a normal propyl group, with a methyl group being particularly preferred, and a chlorine atom being preferred as the halogen atom. Examples of Y include a hydrogen atom, a methyl group and an ethyl group, with a methyl group being particularly preferred, and a fluorine atom being preferred as the halogen atom.
ピラゾール誘導体の塩としては、例えばナトリウム、カ
リウムなどのアルカリ金属塩、カルシウムなどのアルカ
リ土類金属塩、トリエチルアミンなどとの４級アンモニ
ウム塩などが挙げられる。Examples of salts of pyrazole derivatives include alkali metal salts such as sodium and potassium salts, alkaline earth metal salts such as calcium salts, and quaternary ammonium salts with triethylamine and the like.
本発明化合物の化学構造上の特徴点は、ピラゾール環の
１位が炭素数２または３のアルキル基であり、３位が水
素原子であり、且つベンゾイル基のフェニル環の４位が
一５ＯＩＣＩｌｆｆ基であり、２位が炭素数１．２もし
くは３のアルキル基またはハロゲン原子であり、３位が
水素原子、炭素数１もしくは２のアルキル基またはハロ
ゲン原子である。The chemical structure of the compound of the present invention is characterized in that the 1st position of the pyrazole ring is an alkyl group having 2 or 3 carbon atoms, the 3rd position is a hydrogen atom, and the 4th position of the phenyl ring of the benzoyl group is an 15OICIlff group. The 2nd position is an alkyl group having 1.2 or 3 carbon atoms or a halogen atom, and the 3rd position is a hydrogen atom, an alkyl group having 1 or 2 carbon atoms, or a halogen atom.
本発明化合物は、前記の特公昭５４−３６６４８号公報
に記載されている一般式の化合物に包含されるが、本発
明化合物については全く開示も示唆もされていない。一
方、前記の特開昭６０−５１１７５号公報に記載されて
いる化合物は、除草効果が優れたものであり、本発明化
合物に化学構造上も類似してはいるが、しかし本発明化
合物は更に優れた特異な効果を有するものである。The compound of the present invention is included in the compounds of the general formula described in the above-mentioned Japanese Patent Publication No. 54-36648, but the compound of the present invention is not disclosed or suggested at all. On the other hand, the compound described in JP-A No. 60-51175 has an excellent herbicidal effect and is similar in chemical structure to the compound of the present invention, but the compound of the present invention has a further It has excellent and unique effects.
次に本発明化合物の優れた効果を挙げる。Next, the excellent effects of the compounds of the present invention will be listed.
本発明化合物は、稲に対して薬害が強く水田用には使用
が困難であるが、しかしトウモロコシに対しては薬害が
なく、その雑草に対して極めて低薬量、例えばＩｇ／ｙ
−＋ｂ以下の処理量でも充分に殺草効力を有し、各種の
多種類の雑草に対し卓効を有し殺草スペクトラムが広い
という特徴を有している。また難防除雑草であるキハマ
スゲおよびジョンソングラスに対しても極めて低薬量で
殺草効力を有している。更に、雑草の発芽前の土壌処理
に効果を有すると共に、発芽後の雑草が、かなり大きく
生育した時期に処理しても充分に除草効果を有している
。The compound of the present invention has strong phytotoxic effects on rice, making it difficult to use in paddy fields; however, it has no phytotoxic effects on corn, and can be used against weeds at extremely low doses, such as Ig/y.
It has a sufficient herbicidal effect even at a treatment amount of −+b or less, is highly effective against a wide variety of weeds, and has a wide herbicidal spectrum. It also has a herbicidal effect against weeds that are difficult to control, such as yellow mullet and johnson grass, at extremely low doses. Furthermore, it is effective in treating soil before weeds germinate, and has a sufficient herbicidal effect even when treated after germination when weeds have grown considerably.
本発明化合物は、トウモロコシ以外に小麦に対しても薬
害がなく、その雑草、特に各種の広葉雑草に対しも極め
、て低薬量で除草効果を有している。The compound of the present invention has no phytotoxic effects on wheat as well as corn, and has a herbicidal effect on these weeds, especially various broad-leaved weeds, even at extremely low doses.
本発明化合物が除草効力を示す雑草としては、トウモロ
コシ畑では、例えばヒエ、エノコログサ、オオクサキビ
、キハマスゲ、イチビ、オナモミ、イヌビニ、ジョンソ
ングラスなどが挙げられ、小麦畑では、例えばハコベ、
イヌタデ、ノハラガラシ、ノボロギク、コアカザなどが
挙げられる。Weeds for which the compound of the present invention exhibits herbicidal activity include, in corn fields, for example, barnyard grass, foxtail grass, staghorn grass, yellow sedge, Japanese sedge, Japanese sedge, Japanese snail, and johnson grass; in wheat fields, for example, chickweed,
Examples include Japanese knotweed, Japanese wildflower, Japanese wildflower, and koakaza.
上記のように本発明化合物は、優れた性能を有し実用的
な選択性除草剤である。As mentioned above, the compound of the present invention has excellent performance and is a practical selective herbicide.
次に、本発明化合物は、下記の反応式に従って容易に製
造できる。Next, the compound of the present invention can be easily produced according to the following reaction formula.
電 または Ｏ （式中、Ｘ、 ＹおよびＲは前記と同じ意味を表わす。electric or O (In the formula, X, Y and R have the same meanings as above.
）
反応式（１）は適当な置換基を有する安息香酸と１−置
換−５−ヒドロキシピラゾールを、ＤＣＣ（Ｎ、Ｎ’ジ
シクロへキシルカルボジイミド）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。) Reaction formula (1) is a reaction between benzoic acid having an appropriate substituent and 1-substituted-5-hydroxypyrazole in an inert solvent in the presence of DCC (N, N' dicyclohexylcarbodiimide) and a base. represents the reaction to obtain 4-benzoyl-5-hydroxypyrazole.
ＤＣＣは安息香酸及びピラゾールに対し１．０〜１．５
倍モル、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
ている。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。特に限定されるもので
はないが炭酸カリウム、炭酸ナトリウムなどがすぐれて
いる。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。DCC is 1.0-1.5 for benzoic acid and pyrazole
Any solvent may be used as long as it is inert to the reaction, but tertiary-butyl alcohol, tertiary-amyl alcohol, and isopropyl alcohol are particularly preferred. Although a base is not necessarily required, its use generally improves the yield. Although not particularly limited, potassium carbonate, sodium carbonate, etc. are excellent. The reaction temperature can be anywhere from room temperature to the boiling point of the solvent, but is preferably about 50°C to 100°C.
反応時間は通常０．５〜２０時間程度である。The reaction time is usually about 0.5 to 20 hours.
反応式（２）は適当な置換基を有するベンゾイルクロラ
イドと１−置換−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
体とする反応を示す。Reaction formula (2) shows a reaction between benzoyl chloride having an appropriate substituent and 1-substituted-5-hydroxypyrazole to form a benzoyl ester, which is then 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機塩基）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 uses inert solvents (aromatic hydrocarbons, fatty acid esters, halogenated hydrocarbons,
Ethers, acetonitrile, dimethyl sulfoxide,
N,N'-dimethylformamide, etc.) or in a two-phase system or mixed system of these and water.
This is usually achieved in 10 minutes to 5 hours at room temperature to 100°C in the presence of an inorganic base such as caustic soda, caustic potash, or sodium hydrogen carbonate, or an organic base such as pyridine or triethylamine.
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、炭酸すトリウム等が使用され
る。The rearrangement reaction is achieved using a Lewis acid or base, typified by anhydrous aluminum chloride. Potassium carbonate, calcium hydroxide, thorium carbonate, etc. are used as the base.
ルイス酸も塩基も通常１〜１０倍モル使用される。Both the Lewis acid and the base are usually used in 1 to 10 times the molar amount.
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、ジグライムなどが
あげられる。Although a solvent is not particularly required, it is inert to the reaction, and one with an appropriate boiling point may improve operability, yield, etc. Suitable examples include dioxane and diglyme.
反応温度は通常５０〜１５０℃、反応時間は１５分〜ｌ
Ｏ時間である。The reaction temperature is usually 50 to 150°C, and the reaction time is 15 minutes to 1
It's O time.
本発明の原料となる安息香酸類またはベンゾイルクロラ
イドもまた容易に製造できる。製造法としては種々の方
法があるが、−例を示せば下記の反応式に従って製造で
きる。Benzoic acids or benzoyl chloride, which are raw materials for the present invention, can also be easily produced. There are various manufacturing methods, but for example, it can be manufactured according to the following reaction formula.
↓酸化
（上記式中、ＸおよびＹは前記と同じ意味を表し、
□１１ａＡはハロゲン原子を表す。）
“上記のような反応式に従って合成された安息香
酸を以下に示す。↓Oxidation (in the above formula, X and Y represent the same meanings as above,
□11aA represents a halogen atom. )
“Benzoic acid synthesized according to the above reaction formula is shown below.
第 １ 表 ５ｘｙ
合成法 融点（’Ｃ）ＣＩ Ｈ（
３１１９５〜１９６
Ｃ１１３ＩＩ Ｃ５） ２０４〜２０６
Ｃｚｌｌｓ Ｉｔ ＋５１ １５３
〜１５６（ＣＩｌ：ｔ）ＺＣＩＩ ＩＩ
（５） １５４〜１５６ＣＡ Ｃ１ｈ
（４） ２３６〜２３７ＣＩ Ｃｚｔ
ｌｓ （５１１７１〜１７３ＣＩｌ＋ Ｃ
１１ｚ （４） ２２５〜２２６Ｃ１ｈ
Ｆ （５］ １９４〜１９６安息
香酸はさらに五塩化リン、チオニルクロライドなどの塩
素化剤により通常の方法により容易こベンゾイルクロラ
イドに誘導されうる。一方、５−ヒドロキシピラゾール
は特願昭６１−７６２８７号男細書に記載の方法に従っ
て容易に製造しうる。Table 1 5xy
Synthesis method Melting point ('C) CI H (
31195~196 C113II C5) 204~206
Czlls It +51 153
~156 (CIl:t) ZCII II
(5) 154-156CA C1h
(4) 236-237CI Czt
ls (51171~173CIl+C
11z (4) 225~226C1h
F (5) 194-196 benzoic acid can be further easily converted to benzoyl chloride using a chlorinating agent such as phosphorus pentachloride or thionyl chloride in a conventional manner.On the other hand, 5-hydroxypyrazole can be easily converted to benzoyl chloride using a chlorinating agent such as phosphorus pentachloride or thionyl chloride. It can be easily produced according to the method described in the manual.
次に、本発明について実施例を具体的に挙げて北明する
。ただし、本発明はこれらのみに限定さｈるものではな
い。Next, the present invention will be explained with specific examples. However, the present invention is not limited to these.
〔実施例１〕
１−エチル−４−（２−クロル−３−メチル−４−メタ
ンスルホニルベンゾイル）−５−ヒドロキシピラゾール
の合成（本発明化合物患５）１−エチル−５−ヒドロキ
シピラゾール１．１２ｇ（０，０１モル）をターシャリ
−アミルアルコール２０ｍ１に溶解したのち、２−クロ
ル−３−メチル−４−メタンスルホニル安息香酸２．４
９ ｇ（０，０１モル）、Ｎ、Ｎ’−ジシクロへキシル
カルボジイミド２．０６ ｇ （０，０１モル）、無水
炭酸カリウム０．６９ ｇ （０，００５モル）を加え
、温度を８０℃に保ち、攪拌しながら８時間反応させた
。[Example 1] Synthesis of 1-ethyl-4-(2-chloro-3-methyl-4-methanesulfonylbenzoyl)-5-hydroxypyrazole (Compound of the present invention 5) 1-ethyl-5-hydroxypyrazole 1. After dissolving 12 g (0.01 mol) in 20 ml of tertiary amyl alcohol, 2.4 g of 2-chloro-3-methyl-4-methanesulfonylbenzoic acid
9 g (0.01 mol), 2.06 g (0.01 mol) of N,N'-dicyclohexylcarbodiimide, and 0.69 g (0.005 mol) of anhydrous potassium carbonate were added, and the temperature was raised to 80°C. The mixture was maintained and stirred for 8 hours.
反応終了後、減圧にて溶媒を留去したのちに、水を加え
不溶部分を濾別した。得られた水層をクロロホルムで洗
浄したのちに、濃塩酸を加えてｐｌｌ＜１とし、析出し
た固体を濾取し、水洗後、再結晶（エタノール：水＝９
７１）を行ない、目的物を２、５６ ｇ得た。After the reaction was completed, the solvent was distilled off under reduced pressure, water was added, and the insoluble portion was filtered off. After washing the obtained aqueous layer with chloroform, concentrated hydrochloric acid was added to make pll<1, the precipitated solid was collected by filtration, washed with water, and then recrystallized (ethanol:water = 9
71) to obtain 2.56 g of the desired product.
収率ニア５％
〔実施例２〕
１−エチル−４−（２，３−ジメチル−４−メタンスル
ホニルベンゾイル）−５−ヒドロキシピラゾールの合成
（本発明化合物Ｎ１７）
８５％水酸化カリウム１．３２ ｇ （０，０２モル）
を水１０ｍｆに溶解し、ｌ−エチル−５−ヒドロキシピ
ラゾール２．２４ｇ（０，０２モル）を加えて均一溶液
とした。Yield near 5% [Example 2] Synthesis of 1-ethyl-4-(2,3-dimethyl-4-methanesulfonylbenzoyl)-5-hydroxypyrazole (present compound N17) 85% potassium hydroxide 1.32 g (0.02 mol)
was dissolved in 10 mf of water, and 2.24 g (0.02 mol) of l-ethyl-5-hydroxypyrazole was added to form a homogeneous solution.
さらに、クロロホルム３０ｍｊ２を加えて２層とし、２
．３−ジメチル−４−メタンスルホニルベンゾイルクロ
ライド４．９３ｇ（０，０２モル）を加えて、室温で攪
拌しながら３時間反応させた。反応後、クロロホルム層
を分取し、５％炭酸水素ナトリウム水溶液、水、飽和食
塩水で順次洗浄し、無水硫酸ナトリウムで乾燥後、減圧
にて溶媒を留去し、ピラゾールのベンゾイルエステルの
組物を得た。このエステルに１．４−ジオキサン３ ｍ
ｌを加えて均一としたのち、無水炭酸カリウム４．１４
ｇ（０，０３モル）を加え、温度を１３０℃に上げて
２時間反応させた。反応後、水３０ｍ１を加えて、粗反
応物を溶解後、この水溶液に、クロロホルムを加えて洗
浄し、水層を分取した。得られた水溶液に濃塩酸を加え
、ｐＨ＜１とし、析出した固体を濾取し、水洗後、再結
晶（エタノール：水＝９５＝５）を行ない、目的物を３
．４１ｇ得た。Furthermore, 30mj2 of chloroform was added to make two layers.
．． 4.93 g (0.02 mol) of 3-dimethyl-4-methanesulfonylbenzoyl chloride was added, and the mixture was reacted for 3 hours with stirring at room temperature. After the reaction, the chloroform layer was separated, washed sequentially with a 5% aqueous sodium bicarbonate solution, water, and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a benzoyl ester composition of pyrazole. I got it. Add 3 m of 1,4-dioxane to this ester.
1 of anhydrous potassium carbonate.
g (0.03 mol) was added, the temperature was raised to 130°C, and the reaction was carried out for 2 hours. After the reaction, 30 ml of water was added to dissolve the crude reaction product, and the aqueous solution was washed with chloroform, and the aqueous layer was separated. Concentrated hydrochloric acid was added to the resulting aqueous solution to make the pH <1, and the precipitated solid was collected by filtration, washed with water, and then recrystallized (ethanol:water = 95 = 5) to obtain the desired product.
．． 41g was obtained.
収率：５３％
〔実施例３〕
１−イソプロピル−４−（２−クロル−３−メチル−４
−メタンスルホニルベンゾイル）−５−ヒドロキシピラ
ゾールの合成（本発明化合物患前記実施例１において、
■−エチルー５−ヒドロキシピラゾール１．１２ ｇを
１−イソプロピル−５−ヒドロキシピラゾール１．２６
ｇに代えることを除いては、全く同様の掻作と処理を行
ない、目的化合物を２．５７ ｇ得た。Yield: 53% [Example 3] 1-isopropyl-4-(2-chloro-3-methyl-4
Synthesis of -methanesulfonylbenzoyl)-5-hydroxypyrazole (using the compound of the present invention) In Example 1 above,
■-1.12 g of ethyl-5-hydroxypyrazole to 1.26 g of 1-isopropyl-5-hydroxypyrazole
2.57 g of the target compound was obtained by carrying out exactly the same scraping and treatment except that 2.5 g of the target compound was used.
収率ニア２％
前記実施例１〜３に準じて合成された化合物およびその
物性を、実施例１〜３で得られた化合物も含めて、次の
第２表に示す。Yield near 2% Compounds synthesized according to Examples 1 to 3 and their physical properties, including the compounds obtained in Examples 1 to 3, are shown in Table 2 below.
なお、第２表中のＥｔはエチル基を、ｉ −Ｐｒはイソ
プロピル基を表す。In addition, Et in Table 2 represents an ethyl group, and i-Pr represents an isopropyl group.
第 ２ 表
〔以下、余白〕
本発明化合物を除草剤として施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）。Table 2 [Hereinafter, blank space] When applying the compound of the present invention as a herbicide, a suitable carrier is generally used, such as a solid carrier such as clay, talc, bentonite diatomaceous earth, or water, alcohols (methanol, ethanol, etc.).
芳香族炭化水素類（ベンゼン、トルエン、キシレン等）
、エーテル類、ケトン類、エステルＭ （１％酸エチル
類等）、酸アミド類（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、所望により界
面活性剤２分散剤、Ｑｉ剤、浸透剤、展着剤、安定剤な
どを添加し、乳剤。Aromatic hydrocarbons (benzene, toluene, xylene, etc.)
, ethers, ketones, ester M (1% ethyl acids, etc.), acid amides (dimethylformamide, etc.), and if desired, surfactants 2 dispersants, Qi Emulsions are made by adding agents, penetrating agents, spreading agents, stabilizers, etc.
水和剤、粉剤９粒剤等任意の剤型にて実用に供すること
ができる。It can be put to practical use in any dosage form such as a wettable powder or a 9-grain powder.
また必要に応じて製剤または散布時に他種の除草剤〔例
えば、ファーム・ケミカル・ハンドブック７０． （
１９８４）に記載された化合物〕、各種殺虫剤、殺菌剤
、共力剤などと混合施用してもよい。In addition, other types of herbicides may be used during formulation or spraying as necessary [for example, Farm Chemical Handbook 70. (
1984)], various insecticides, fungicides, synergists, etc. may be applied in combination.
次に具体的に本発明化合物を用いる場合の製剤の配合例
を示す。部は重量を示す。但し本発明の配合例は、これ
らのみに限定されるものではない。Next, specific formulation examples of formulations using the compounds of the present invention will be shown. Parts indicate weight. However, the formulation examples of the present invention are not limited to these only.
■丘胴工 水和剤
本発明化合物 阻４ ・・・・・・６０部ジー
クライトＰＦＰ ・・・・・・３３部（カオ
リン系クレー：ジ−クライト工業側商品名）
ツルポール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■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■商品名）以上を均一に混
合粉砕して水和剤とする。■Hyadoko Wettable powder Compound of the present invention Inhibition 4...60 parts Siegrite PFP...33 parts (Kaolin clay: Zikrite Industry trade name) Tsurupol 5039... ...5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■trade name) Carplex (anti-caking agent) ...2 parts (white carbon: Shionogi & Co., Ltd.) ■Product name) Mix and grind the above ingredients uniformly to make a wettable powder.
ｙ會銖ｌ 水和剤
本発明化合物 患５ ・・・・・・６０部ジー
クライトＰＰＰ ・・・・・・３３部（カオ
リン系クレー：ジ−クライト工業側商品名）
ツルポール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■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■商品名）以上を均一に混
合粉砕して水和剤とする。Hydrating agent Compound of the present invention Patient 5: 60 parts Siegrite PPP: 33 parts (Kaolin clay: Siecrite Industrial trade name) Tsurupol 5039... ...5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■trade name) Carplex (anti-caking agent) ...2 parts (white carbon: Shionogi & Co., Ltd.) ■Product name) Mix and grind the above ingredients uniformly to make a wettable powder.
ＡＢＬ倒」−水和剤
本発明化合物 隘７ ・・・・・・６０部ジー
クライトＰＦＰ ・・・・・・３３部（カオ
リン系クレー：ジ−クライト工業側商品名）
ツルポール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■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：塩野義製薬側商品名）以上を均一に混
合粉砕して水和剤とする。ABL - Hydrating agent Compound of the present invention 7...60 parts Siegrite PFP...33 parts (Kaolin clay: Sickleite Industrial product name) Tsurupol 5039... ...5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■trade name) Carplex (anti-caking agent) ...2 parts (white carbon: Shionogi & Co., Ltd.) Side product name) The above is mixed and pulverized uniformly to make a wettable powder.
へＢＬ例」ユ 水和剤
本発明化合物 ｍ１２ ・・・・・・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■商品名）
ツルポール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
：東邦化学住荀商品名）
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■商品名）以上を均一に混
合粉砕して水和剤とする。To BL Example "U Wettable powder Compound of the present invention m12...60 parts Siegrite PFP...33 parts (Kaolin clay: Sieglite Kogyo ■trade name) Tsurupol 5039...・5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Kagaku Shushō brand name) Carplex (anti-caking agent) 2 parts (white carbon: Shionogi & Co., Ltd.) ■Product name) Mix and grind the above ingredients uniformly to make a wettable powder.
皿査開工 水和剤
本発明化合物 隘１４ ・・・・・・６０部ジー
クライトＰＰＰ ・・・・・・３３部（カオ
リン系クレー：ジ−クライト工業側商品名）
ツルポール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■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０＠商品名）以上を均一に
混合粉砕して水和剤とする。Discretionary powder Wettable powder Compound of the present invention 14...60 parts Siegrite PPP...33 parts (Kaolin clay: Zigrite Industrial product name) Tsurupol 5039...・5 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■Product name) Carplex (anti-caking agent) 2 parts (White carbon: Shionogi & Co., Ltd. 0 @Product name) Mix and grind the above ingredients uniformly to make a wettable powder.
筐査■工 乳剤
本発明化合物 阻６ ・・・・・弓、５部キ
シ し ン ・・・・
・・７ ａ、 ５ 部ジメチルホルムアミド
・・・・・・１５部ツルポール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■商品名）
以上を均一に混合して乳剤とする。Emulsion Compound of the Invention 6... Bow, Part 5
Shin...
・・7 a, 5 parts dimethylformamide
・・・・・・Part 15 Tsurupol 2680 ・・・
...5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■trade name) The above is mixed uniformly to form an emulsion.
筐金■エ フロアブル
本発明化合物 １１ｈ２ ・・・・・・４０
部アゲリリンルＢ−７１０・・・・・・１０部（非イオ
ン性界面活性剤：花王■商品名）ルノックス１００Ｏｃ
・・・・・・０．５部（アニオン性界面活性
剤：東邦化学■商品名）１％ロドボール水
・・・・・・２０部（増粘剤：ローン・ブーラン社商品
名）水 ・・・・
・・２９．５部以上を均一に混合し、フロアブル剤とす
る。Kogane E Flowable Compound of the Invention 11h2 ・・・・・・40
Part Agelirinlu B-710...10 parts (Nonionic surfactant: Kao brand name) Lunox 100Oc
...0.5 part (anionic surfactant: Toho Chemical ■trade name) 1% Rhodobol water
・・・・・・20 parts (thickener: Lone Boulin product name) Water ・・・・
...Mix 29.5 parts or more uniformly to make a flowable agent.
■金Ｍ主 フロアブル
本発明化合物 １１ｈ５ ・・・・・・４０
部アゲリリンルＢ−７１０・・・・・弓０部（非イオン
性界面活性剤：花王ａ１商品名）ルノックス１ｏｏｏｃ
・・・・・・０．５部（アニオン性界面活性
剤：東邦化学■商品名）１％ロドボール水
・・・・・・２０部（増粘剤：ローン・ブーラン社商品
名）水 ・・・・・・
２９．５部以上を均一に混合し、フロアブル剤とする。■ Gold M main flowable compound of the present invention 11h5 ・・・・・・40
Part Agelirinlu B-710... 0 parts (nonionic surfactant: Kao a1 brand name) Lunox 1oooc
...0.5 part (anionic surfactant: Toho Chemical ■trade name) 1% Rhodobol water
・・・・・・20 parts (thickener: Lone Boulin product name) Water ・・・・・・
29.5 parts or more are mixed uniformly to form a flowable agent.
況論」Ｌ［−フロアブル
本発明化合物 阻１２ ・・・・・・４０部アゲ
リリンルＢ−７１０・・・・・・１０部（非イオン性界
面活性剤：花王側商品名）ルノックス１００ＯＣ・・・
・・・０．５部（アニオン性界面活性剤：東邦化学０１
商品名）１％ロドボール水 ・・・・・・２
０部（増粘剤：ローン・ブーラン社商品名）水
・・・・・・２９．５部以
上を均一に混合し、フロアブル剤とする。L[-Flowable Compound of the Invention 12...40 parts Ageryrin B-710...10 parts (nonionic surfactant: Kao brand name) Lunox 100OC...
...0.5 part (anionic surfactant: Toho Chemical 01
Product name) 1% Rhodobol water ・・・・・・2
0 parts (thickener: Lone Boulin product name) water
... 29.5 parts or more are mixed uniformly to form a flowable agent.
Ｅイ１殊上」−液剤
本発明化合物 １１１１１Ｌ５のソーダ塩 ・・・
３０部ニフボール ・・・・・・１０
部（非イオン性界面活性剤：日産化学ａ１商品名）水
・・・・・・６０
部以上を均一に混合して液剤とする。E-1-Soda salt of the compound of the present invention 11111L5...
Part 30 Nifball...10
Part (Nonionic surfactant: Nissan Chemical A1 brand name) Water
・・・・・・60
Mix 10 parts or more uniformly to make a liquid.
几３１舛」」−液剤
ツルポール Ｗ−１５０、・・・・・・１０部（非イオ
ン性界面活性剤：東邦化学■商品名）水
・・・・・・８０部以上を均
一に混合して液剤とする。31 Masu” - Liquid Tsurupol W-150, 10 parts (Non-ionic surfactant: Toho Chemical ■Product name) Water
... 80 parts or more are mixed uniformly to form a liquid agent.
使用に際しては上記水和剤、乳剤、フロアブル剤、液剤
は水で５０〜１０００倍に希釈して、有効成分がｌｈａ
当たり０．００１〜５ ｋｇの割合になるように散布す
る。When using, the above-mentioned hydrating powders, emulsions, flowable preparations, and liquid preparations should be diluted 50 to 1000 times with water to ensure that the active ingredients are lha
Spray at a ratio of 0.001 to 5 kg per person.
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（ｈａ）当たり０．ＯＯ
１〜５ｋｇ程度の割合が適当である。In addition, the compound of the present invention can be applied to control various weeds in non-agricultural lands such as playgrounds, open spaces, and railroad tracks, in addition to agricultural and horticultural fields such as fields, paddy fields, and orchards, and the amount of application depends on the application situation. There are differences depending on the application period, target grass species, cultivated crops, etc., but in general, the application rate is 0.00% per hectare (ha). OO
A proportion of about 1 to 5 kg is appropriate.
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 effects of the compounds of the present invention will be specifically explained by giving test examples.
μ」ｌ舛：」−土壌処理による除草効果試験線４０ｃｍ
、横４００．深さ１２ｃｎ＋のプラスチック製箱に殺菌
した洪積土壌を入れ、トウモロコシコムギ、ヒエ、エノ
コログサ、メヒシバ、オオクサキビ、イヌビニ、イヌタ
デ、イチビ、ハコベ、ノハラガラシ、ノボロギク、コア
カザの種子をそれぞれ播種し、またキハマスゲの塊茎を
植えつけて、約１ｃｍ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。μ"l舛:" - Test line for herbicidal effect by soil treatment 40cm
, width 400. Sterilized diluvial soil was placed in a plastic box with a depth of 12 cn+, and seeds of corn wheat, barnyard grass, foxtail grass, Japanese grasshopper, Japanese knotweed, Japanese knotweed, Japanese knotweed, Japanese thornweed, chickweed, field mustard, yellow chestnut, and koakaza were sown. After planting the tubers and covering them with soil to a depth of about 1 cm, the amount of the active ingredient was uniformly spread over the soil surface at a predetermined ratio.
散布の際の薬液は、前記配合例の液剤、水和剤、乳剤ま
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
果を下記の判定基準に従い調査した。The chemical solution used for spraying was the liquid formulation, wettable powder, emulsion or flowable formulation of the formulation example described above, diluted with water and sprayed over the entire surface with a small sprayer. Three weeks after spraying the chemical solution, the herbicidal effect on various weeds was investigated according to the following criteria.
判定基準
５・・・殺草率９０％以上（はとんど完全枯死）４・・
・殺草率７０〜９０％
３・・・殺草率４０〜７０％
２・・・殺草率２０〜４０％
１・・・殺草率 ５〜２０％
Ｏ・・・殺草率 ５％以下（はとんど効力なし）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 Criterion 5: Weed killing rate of 90% or more (almost complete death) 4...
・Weed killing rate 70-90% 3... Weed killing rate 40-70% 2... Weed killing rate 20-40% 1... Weed killing rate 5-20% O... Weed killing rate 5% or less (Haton However, the above-mentioned herbicidal rate was determined by measuring the weight of above-ground plants in the chemically treated area and the weight of above-ground plants in the non-treated area using the following formula.
また各種作物に対する薬害を下記判定基準に従い調査し
た。In addition, phytotoxicity to various crops was investigated according to the following criteria.
判定基準
５・・・作物はほとんど完全枯死
４・・・作物に対する薬害が顕著
３・・・作物に対する薬害が認められる２・・・作物に
対する薬害が若干認められる１・・・作物に対する薬害
は殆んど認められない０・・・作物に対する薬害は認め
られないこの結果は第３表に示す。Criterion 5: The crop is almost completely dead 4: The phytotoxicity of the crop is significant 3: The phytotoxicity of the crop is observed 2: Some phytotoxicity of the crop is observed 1: There is almost no phytotoxicity of the crop 0: No phytotoxicity observed on crops The results are shown in Table 3.
なお、表中の処理薬量のｇ／ａはｇ／アールである。In addition, g/a of the treatment chemical amount in the table is g/are.
拭鼓斑二又 Ｗ藁処理による除草効果試験線４０ＣＩ、
横４０ｃｍ、深さ１２ｃｍのプラスチック製箱に殺菌し
た洪積土壌を入れ、トウモロコシコムギ、ヒエ、エノコ
ログサ、メヒシバ、オオクサキビ、イヌビニ、イヌタデ
、イチビ、ハコベ、ノハラガラシ、ノボロギク、コアカ
ザ、オナモミの種子をそれぞれ播種し、またキハマスゲ
の塊茎を植えつけて、約１ ｃｍ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。Wiping spot bifurcated W herbicidal effect test line by straw treatment 40CI,
Sterilized diluvial soil was placed in a plastic box measuring 40 cm wide and 12 cm deep, and seeds of corn wheat, barnyard grass, foxtail grass, snailweed, Japanese cane, Japanese knotweed, Japanese knotweed, Japanese jackweed, chickweed, wild mustard, yellow daisy, Japanese cypress, and Japanese fir were sown. Then, I planted tubers of yellow lily and covered with soil to a depth of about 1 cm. When each plant reached the 2-3 leaf stage, the active ingredient was uniformly sprayed onto the stems and leaves so that the amount of the active ingredient was at a predetermined ratio.
散布の際の薬液は、前記配合例の液剤、水和剤、乳剤ま
たはフロアブル剤を水で希釈して小型スプレーで各種植
物の茎葉部の全面に散布した。The chemical solution used for spraying was the liquid formulation, wettable powder, emulsion, or flowable formulation of the formulation example described above, which was diluted with water and sprayed over the entire surface of the stems and leaves of various plants using a small sprayer.
薬液散布３週間後に各種雑草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。Three weeks after spraying the chemical solution, the herbicidal effect on various weeds was investigated according to the criteria of Test Example-1.
結果を第４表に示す。The results are shown in Table 4.
Ｍ」ｕ性二」−ジョンソングラス（塊茎）に対する菫葉
処理除草効果試験
直径１２ｃｍ、深さ１２ｃｍののプラスチック製ポット
に殺菌した洪積土壌を入れ、ジョンソングラスの塊茎を
約１．５ｃｍの深さに埋め込んだ。- Test of herbicidal effect of violet leaf treatment on Johnson grass (tubers) Sterilized diluvial soil was placed in a plastic pot with a diameter of 12 cm and a depth of 12 cm, and Johnson grass tubers were placed in a plastic pot with a depth of approximately 1.5 cm. embedded in it.
ジョンソングラスが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。When the Johnson grass reached the 2-3 leaf stage, the active ingredients were uniformly sprayed onto the stems and leaves at a predetermined ratio.
散布の際の薬液は、前記配合例の液剤、水和剤、乳剤ま
たはフロアブル剤を水で希釈して小型スプレーで茎葉部
の全面に散布した。The chemical solution used for spraying was the liquid formulation, wettable powder, emulsion or flowable formulation of the formulation example described above, which was diluted with water and sprayed over the entire surface of the foliage using a small sprayer.
薬液散布４週間後に除草効果を試験例−１の判定基準に
従い調査した。Four weeks after spraying the chemical solution, the herbicidal effect was investigated according to the criteria of Test Example-1.
結果を第５表に示す。The results are shown in Table 5.
なお、第３表、第４表および第５表中の化合物の欄のＡ
、Ｂ、Ｃ，ＤおよびＥは、比較のための対照化合物（公
知化合物）で、その構造式は後記に記載した。In addition, A in the compound column in Tables 3, 4 and 5
, B, C, D and E are control compounds (known compounds) for comparison, and their structural formulas are described below.
第３表
第３表頷き）
第３表頷き）
第３表＠＠）
一下、余白〕
第４表
第４表頷き）
第４表億諺）
第４表頷き）
は下、余白〕
第５表 第５表（続き）前記の
第３表より第５表までの対照化合物は、下記のとおりで
ある。Table 3 Table 3 Nod) Table 3 Nod) Table 3 @@) Bottom, margin〕 Table 4 Table 4 Nod) Table 4 Hundred Proverbs) Table 4 Nod) Bottom, margin〕 Table 5 Table 5 (Continued) The control compounds in Tables 3 through 5 above are as follows.
対照化合物Ａ： Ｃ１１゜ 対照化合物Ｂ： ＣＨ２ 対照化合物Ｃ： ＣＨ３ 対照化合物Ｄ： ＣＨ３０ 対照化合物Ｅ：Control compound A: C11゜ Control compound B: CH2 Control compound C: CH3 Control compound D: CH30 Control compound E:
Claims (5)
Ｘは、炭素数１、２もしくは３のアルキル基またはハロ
ゲン原子を、Ｙは、水素原子、炭素数１もしくは２のア
ルキル基またはハロゲン原子を表す。〕(1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼Pyrazole derivatives or their salts represented by (I). [In the above formula, R is an alkyl group having 2 or 3 carbon atoms,
X represents an alkyl group having 1, 2 or 3 carbon atoms or a halogen atom, and Y represents a hydrogen atom, an alkyl group having 1 or 2 carbon atoms or a halogen atom. ]
ル基または塩素原子で、Ｙがメチル基である特許請求の
範囲第１項記載のピラゾール誘導体またはその塩。(2) The pyrazole derivative or its salt according to claim 1, wherein R is an ethyl group or an isopropyl group, X is a methyl group or a chlorine atom, and Y is a methyl group.
は２種以上を有効成分として含有する選択性除草剤。 〔上記式中、Ｒは、炭素数２または３のアルキル基を、
Ｘは、炭素数１、２もしくは３のアルキル基またはハロ
ゲン原子を、Ｙは、水素原子、炭素数１もしくは２のア
ルキル基またはハロゲン原子を表す。〕(3) A selective herbicide containing one or more pyrazole derivatives or salts thereof as an active ingredient represented by the general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼. [In the above formula, R is an alkyl group having 2 or 3 carbon atoms,
X represents an alkyl group having 1, 2 or 3 carbon atoms or a halogen atom, and Y represents a hydrogen atom, an alkyl group having 1 or 2 carbon atoms or a halogen atom. ]
３項記載の選択性除草剤。(4) The selective herbicide according to claim 3, which is selective for corn.
の選択性除草剤。(5) The selective herbicide according to claim 3, which is selective for wheat.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26686286A JPS63122672A (en) | 1986-11-10 | 1986-11-10 | Pyrazole derivative and selective herbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26686286A JPS63122672A (en) | 1986-11-10 | 1986-11-10 | Pyrazole derivative and selective herbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63122672A true JPS63122672A (en) | 1988-05-26 |
Family
ID=17436690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26686286A Pending JPS63122672A (en) | 1986-11-10 | 1986-11-10 | Pyrazole derivative and selective herbicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63122672A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0629623A1 (en) * | 1992-03-03 | 1994-12-21 | Idemitsu Kosan Company Limited | Pyrazole derivative |
| WO1995004054A1 (en) * | 1993-08-02 | 1995-02-09 | Idemitsu Kosan Co., Ltd. | Pyrazole derivative |
| US5756759A (en) * | 1993-11-09 | 1998-05-26 | Idemitsu Kosan Co., Ltd. | Pyrazole compounds having a thiochroman ring and pesticides containing such compounds |
| US5767289A (en) * | 1993-08-02 | 1998-06-16 | Idemitsu Kosan Company, Limited | Aromatic carboxylic acid bicyclic sulfur compounds |
| WO1998042678A1 (en) * | 1997-03-24 | 1998-10-01 | Dow Agrosciences Llc | 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides |
| WO1998052926A3 (en) * | 1997-05-23 | 1999-02-25 | Dow Agrosciences Llc | 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0625133A (en) * | 1992-07-04 | 1994-02-01 | Nippon Nohyaku Co Ltd | N-@(3754/24)substituted benzyloxy) imine derivative, its production and agricultural and horticultural fungicide |
-
1986
- 1986-11-10 JP JP26686286A patent/JPS63122672A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0625133A (en) * | 1992-07-04 | 1994-02-01 | Nippon Nohyaku Co Ltd | N-@(3754/24)substituted benzyloxy) imine derivative, its production and agricultural and horticultural fungicide |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0629623B1 (en) * | 1992-03-03 | 1999-05-19 | Idemitsu Kosan Company Limited | Pyrazole derivative |
| EP0629623A1 (en) * | 1992-03-03 | 1994-12-21 | Idemitsu Kosan Company Limited | Pyrazole derivative |
| US6063936A (en) * | 1993-08-02 | 2000-05-16 | Idemitsu Kosan Co., Ltd. | Aromatic carboxylic acid bicyclic sulfur compounds |
| US5767289A (en) * | 1993-08-02 | 1998-06-16 | Idemitsu Kosan Company, Limited | Aromatic carboxylic acid bicyclic sulfur compounds |
| CN1046719C (en) * | 1993-08-02 | 1999-11-24 | 出光兴产株式会社 | Pyrazole derivative, herbicide containing the same, and intermediate thereof |
| WO1995004054A1 (en) * | 1993-08-02 | 1995-02-09 | Idemitsu Kosan Co., Ltd. | Pyrazole derivative |
| US6103668A (en) * | 1993-08-02 | 2000-08-15 | Idemitsu Kosan Co., Ltd. | Pyrazole derivatives |
| US6136755A (en) * | 1993-08-02 | 2000-10-24 | Idemitsu Kosan Co., Ltd. | Pyrazole derivatives |
| US6677460B1 (en) | 1993-08-02 | 2004-01-13 | Idemitsu Kosan Company, Limited | Aromatic carboxylic acid bicyclic sulfur compounds |
| US5849926A (en) * | 1993-11-09 | 1998-12-15 | Idemitsu Kosan Co., Ltd. | Pyrazole derivatives and herbicides containing the same |
| US5756759A (en) * | 1993-11-09 | 1998-05-26 | Idemitsu Kosan Co., Ltd. | Pyrazole compounds having a thiochroman ring and pesticides containing such compounds |
| WO1998042678A1 (en) * | 1997-03-24 | 1998-10-01 | Dow Agrosciences Llc | 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides |
| WO1998052926A3 (en) * | 1997-05-23 | 1999-02-25 | Dow Agrosciences Llc | 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides |
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