JPS62181263A - N-substituted azole derivative and fungicidal composition for agricultural and horticultural use containing said derivative as active component - Google Patents
N-substituted azole derivative and fungicidal composition for agricultural and horticultural use containing said derivative as active componentInfo
- Publication number
- JPS62181263A JPS62181263A JP2299886A JP2299886A JPS62181263A JP S62181263 A JPS62181263 A JP S62181263A JP 2299886 A JP2299886 A JP 2299886A JP 2299886 A JP2299886 A JP 2299886A JP S62181263 A JPS62181263 A JP S62181263A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- agricultural
- compound
- lower alkyl
- 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
- -1 N-substituted azole Chemical class 0.000 title claims abstract description 30
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 title claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 25
- 239000000417 fungicide Substances 0.000 abstract description 11
- 238000003756 stirring Methods 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 9
- 238000010438 heat treatment Methods 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002585 base Substances 0.000 abstract description 4
- 229910000104 sodium hydride Inorganic materials 0.000 abstract description 4
- 239000012312 sodium hydride Substances 0.000 abstract description 4
- 231100000674 Phytotoxicity Toxicity 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 3
- 159000000000 sodium salts Chemical class 0.000 abstract description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000003449 preventive effect Effects 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 241000209094 Oryza Species 0.000 description 10
- 235000007164 Oryza sativa Nutrition 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 235000009566 rice Nutrition 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 230000003902 lesion Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003905 agrochemical Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- 241001330975 Magnaporthe oryzae Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000007884 disintegrant Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KMHZPJNVPCAUMN-UHFFFAOYSA-N Erbon Chemical compound CC(Cl)(Cl)C(=O)OCCOC1=CC(Cl)=C(Cl)C=C1Cl KMHZPJNVPCAUMN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000519695 Ilex integra Species 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FXCJYMLJTUZGDU-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=C(Cl)C=C1Cl FXCJYMLJTUZGDU-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- VIRWKAJWTKAIMA-UHFFFAOYSA-N 2-chloroethyl acetate Chemical compound CC(=O)OCCCl VIRWKAJWTKAIMA-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
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- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
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- 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
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- 238000007865 diluting Methods 0.000 description 1
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- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 239000010433 feldspar Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 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
- 230000011890 leaf development Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- MGMWQSVSOGNGPL-UHFFFAOYSA-N methyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OC MGMWQSVSOGNGPL-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- GZQUFIUZBLOTMM-UHFFFAOYSA-N pentyl methanesulfonate Chemical compound CCCCCOS(C)(=O)=O GZQUFIUZBLOTMM-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- FHYUCVWDMABHHH-UHFFFAOYSA-N toluene;1,2-xylene Chemical group CC1=CC=CC=C1.CC1=CC=CC=C1C FHYUCVWDMABHHH-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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Ｎ−置換アゾール誘導体に関し、該誘導体
は水田、畑地、または果樹園などにおける農園芸用殺菌
剤として用いることができる。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel N-substituted azole derivative, which can be used as an agricultural and horticultural fungicide in paddy fields, fields, orchards, etc.
従来の農業用殺菌剤には、抗生物質剤、有機リン剤、有
機合成殺菌剤等がある。Conventional agricultural fungicides include antibiotics, organic phosphorus agents, organic synthetic fungicides, and the like.
従来の農園芸用殺菌剤はイネいもち病やイネ白葉枯病キ
ーウリ斑点細菌病などの細菌病に対し□効力が不十分で
あったり、薬剤耐性菌が問題となったり、作物に薬害を
生じたり、また経済性に問題があるなどの欠点を有する
。Conventional fungicides for agricultural and horticultural use are insufficiently effective against bacterial diseases such as rice blast, rice blight, and cucurbit bacterial spot, or may cause problems with drug-resistant bacteria or cause chemical damage to crops. , and also has disadvantages such as economical problems.
本発明はこれら欠点をおぎなう有用な農園芸用殺菌剤を
提供するものである。The present invention provides a useful agricultural and horticultural fungicide that overcomes these drawbacks.
本発明者は、下記式（１）で示されるＮ−置換アゾール
誘導体を利用することにより、従来の農園芸用殺菌剤の
欠点をおぎない、高い防除効果が得られ、植物体に薬害
などの悪影響を及ぼさないことを見い出し、本発明を完
成するに至った。The present inventor has discovered that by using an N-substituted azole derivative represented by the following formula (1), it is possible to overcome the drawbacks of conventional agricultural and horticultural fungicides, obtain a high pesticidal effect, and cause adverse effects such as phytotoxicity on plants. The present invention was completed based on the discovery that the present invention does not affect the performance of the invention.
（式中、Ｒは水素原子、ハロゲン原子、メチル基又はメ
トキシ基を示し、Ｒ１は水素原子、低級アルキル基又は
ハロゲン原子で置換されたフェニル基を示し、Ｒ２は水
素原子又は低級アルキル基を示す。ｎは１または２の整
数を示し、ｍは０又はｌの整数を示す。Ａｚはピラゾリ
ル基、イミダゾリル基又は１．２．４−トＩＪアゾリル
基を示す）
本発明の式（１）の化合物は、式
Ａｚ −Ｈ（Ｕ）
（式中、Ａｚは前記と同じ意味を有する）で表わされる
アゾール類をたとえば水素化ナトリウム、ナトリウム、
メタル−トなどの適当な金属塩基類と溶媒中好ましくは
０〜８゜０Ｃで反応することにより、アルカリ金属塩、
好ましくはナトリウム塩とし、式
（式中、ＬＲ＋＋ Ｒ２ｔ ｎ、 ｒｎは前記と同シ意
味を有す、Ｒ４は低級アルキル基を示す。）で表わされ
るメタンスルホネート類と共に攪拌し、かつ好ましくは
４０〜１２０℃に加熱することにより得ることができる
。(In the formula, R represents a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, R1 represents a hydrogen atom, a lower alkyl group, or a phenyl group substituted with a halogen atom, and R2 represents a hydrogen atom or a lower alkyl group. . n represents an integer of 1 or 2, m represents an integer of 0 or l; Az represents a pyrazolyl group, an imidazolyl group, or a 1.2.4-toIJ azolyl group) of the formula (1) of the present invention. The compound is an azole represented by the formula Az -H(U) (wherein Az has the same meaning as above), for example, sodium hydride, sodium,
Alkali metal salts, by reacting with suitable metal bases such as metal salts in a solvent preferably at 0 to 8°
Preferably, it is made into a sodium salt, and stirred with a methanesulfonate represented by the formula (wherein, LR++ R2t n, rn have the same meanings as above, and R4 represents a lower alkyl group), and preferably 40 to It can be obtained by heating to 120°C.
溶媒としては、Ｎ、Ｎ−ジメチルホルムアミドおよびＮ
、Ｎ−ジメチルアセトアミドのようなアミド類あるいは
アセトニトリルプロピオニトリルのようなニトリル類が
あげられる。Solvents include N,N-dimethylformamide and N
, amides such as N-dimethylacetamide, and nitrites such as acetonitrile and propionitrile.
式（冒）で表わされる化合物は次の方法により得ること
ができる。The compound represented by formula (h) can be obtained by the following method.
式
（式中、Ｒ，Ｒ，、ｎ、 ｍは前記と同じ意味を有する
。）
で表わされる化合物を式
％式％（）
（式中、Ｒ２は前記と同じ意味を有し、Ｒ３は低級アル
キル基を示し、Ｘはハロゲン原子を示す。）
で表わされるα−ハロゲノ−α−アルキル酢酸エステル
を脱酸剤の存在下、溶媒中、好ましくはＯ〜１００’Ｃ
で反応させることにより、式
（式中、Ｒ＋ Ｒ１＋ Ｒ２，Ｒ３，ｎ、 ｍは前記と
同じ意味を有する。）
で表わされる化合物を得る。ここでいう脱殻剤としては
、たとえば、アルカリ金属の水酸化物（ＮａＯＨ，ＫＯ
Ｈなど）アルカリ金属アルコラード（ナトリウムアルコ
ラードなと）、アおよび、ピリジン、トリアルキルアミ
ン、ジアルキルアニリンなどの有機塩基があげられる。A compound represented by the formula (wherein R, R,, n, and m have the same meanings as above) is a compound represented by the formula % formula () (wherein R2 has the same meaning as above, and R3 is a lower (represents an alkyl group, and X represents a halogen atom.) α-halogeno-α-alkyl acetate represented by
By reacting with , a compound represented by the formula (wherein R+ R1+ R2, R3, n, and m have the same meanings as above) is obtained. Examples of dehulling agents mentioned here include alkali metal hydroxides (NaOH, KO,
(H, etc.), alkali metal alcoholades (such as sodium alcoholade), organic bases such as pyridine, trialkylamines, and dialkylanilines.
また溶媒としては、水あるいは有機＠媒、たトエハベン
ゼン、トルエン、キシレンナトの芳香族炭化水素、ヘキ
サン、ベプタン、石油、ベンジンなどの脂肪族炭化水素
、クロロホルム、ジクロロメタンなどのハロゲン化水素
、ジメチルホルムアミド、ジメチルアセドアアミド類、
ジエチルエーテル、１．２−ジメトキシエタン、テトラ
ヒドロフラン、ジオキサンなどのエーテル類、アセトニ
トリル、プロピオントリルなどのニトリル類、アセトン
、ジイソプロピルケトンなどのケトン類などを用いるこ
とができる。Examples of solvents include water or organic solvents, aromatic hydrocarbons such as toehabenzene, toluene, and xylene, aliphatic hydrocarbons such as hexane, beptane, petroleum, and benzene, hydrogen halides such as chloroform and dichloromethane, dimethylformamide, dimethylacedoamides,
Ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, and dioxane, nitriles such as acetonitrile and propiontrile, and ketones such as acetone and diisopropyl ketone can be used.
この弐■で表わされる化合物を、例えばエーテル類（ジ
エチルエーテル、テトラヒドロフランなど）中、好まし
くは０〜８０°ＣでＬ ｉ Ａ Ｉ Ｈ，で還元するこ
とにより式（式中、Ｒ＋ Ｒ＋＋ Ｒ２ｙ ｎ、 ｍは
前記トｒｆｌＬＪ！：味を有する。）
で表わされる化合物を得る。さらに式（Ｖｌｌ）で表わ
される化合物を塩基の存在下、溶媒中、０〜１５０°Ｃ
で式
％式％）
（式中Ｒ４は低級アルキル基を、Ｘは）・ロゲン原子を
示す）で示されるノ・ロゲン化アルカルスルホニルと反
応させることにより、弐（１）で表わされるメタンスル
ホナートを得ることができる。ここでいう好ましい塩基
としては、トリエチルアミン、ピリジンなどの有機塩基
であり、溶媒としては、ベンゼン、トルエンキシレンな
どの芳香族炭化水素、ジエチルエーテル、ジイソプリビ
ルエーテル、１．２−ジメトキシエタン、テトラヒドロ
フラン、ジオキサンのエーテル類、アセトニトリル、プ
ロピオニトリルなどのニトリル類、アセトン、ジイソプ
ロピルケトンなどのケトン類、酢酸゛エチルなどのエス
テル類が好ましい。又、式（％’ｕ）’の化合物とシテ
ハ例えばＣＨ，ＳＯ，Ｃｚ、 ＣＨ３５ｏ、Ｂｒ、
ＣＩ（３Ｃ）（２８０２（’ｔなどがあげられるが、こ
の中では経済的な面からＣＨ３５ｏ、ｃｔが好ましい。The compound represented by 2 is reduced with Li A I H, in an ether (diethyl ether, tetrahydrofuran, etc.), preferably at 0 to 80°C, to form a compound of the formula (wherein R+ R++ R2y n, m has the above-mentioned trflLJ!: taste.) A compound represented by the following formula is obtained. Furthermore, a compound represented by formula (Vll) was added at 0 to 150°C in a solvent in the presence of a base.
Methanesulfonate represented by 2 (1) can be obtained by reacting with a rogenated alkalsulfonyl represented by the formula % (formula % formula %) (in the formula, R4 represents a lower alkyl group and X represents a rogen atom). can be obtained. Preferred bases here include organic bases such as triethylamine and pyridine, and solvents include aromatic hydrocarbons such as benzene and toluene xylene, diethyl ether, diisoprivylether, 1,2-dimethoxyethane, and tetrahydrofuran. Preferred are ethers of dioxane, nitriles such as acetonitrile and propionitrile, ketones such as acetone and diisopropyl ketone, and esters such as ethyl acetate. Also, compounds of formula (%'u)' and compounds such as CH, SO, Cz, CH35o, Br,
Examples include CI(3C)(2802('t), among which CH35o and ct are preferred from an economical point of view.
原料化合物は好ましくは当モル比で使用し、まれには反
応成分の一方、又は他方を過剰に使用するのが有利なこ
ともある。反応混合物は常法で、たとえば水を加え、か
つ相を分離させることにより得られる。粗生成物は純度
の高いものも得られるが、再結晶またはカラムクロマト
グラフィーによって精製することができる。The starting compounds are preferably used in equimolar ratios, and in rare cases it may be advantageous to use an excess of one or the other of the reaction components. The reaction mixture is obtained in customary manner, for example by adding water and separating the phases. The crude product, which can be obtained in high purity, can be purified by recrystallization or column chromatography.
本発明化合物を農園芸用殺菌剤の有効成分として使用す
る場合、本発明化合物を１種又は２種以上使用してもよ
い。When using the compound of the present invention as an active ingredient of a fungicide for agriculture and horticulture, one or more compounds of the present invention may be used.
本発明化合物を農園芸用殺菌剤として使用する場合、使
用目的に応じてそのままか、または効果を助長あるいは
安定にするために農薬補助剤を混用して、農薬製造分野
において一般に行われている方法により、粉剤、細粒剤
、粒剤、水和剤、フロアブル剤および乳剤等の製造形態
にして使用することができる。When the compound of the present invention is used as a fungicide for agricultural and horticultural purposes, depending on the purpose of use, it may be used as is, or it may be mixed with an agrochemical adjuvant to enhance or stabilize the effect, using methods commonly used in the field of agrochemical manufacturing. Accordingly, it can be used in the production form of powders, fine granules, granules, wettable powders, flowable preparations, emulsions, etc.
これらの種々の製剤は実際の使用に際しては、直接その
まま使用するか、または水で所望の濃度に希釈して使用
することができる。In actual use, these various formulations can be used directly or diluted with water to a desired concentration.
ここに言う農薬補助剤としては担体（希釈剤）およびそ
の他の補助剤たとえば展着剤、乳化剤、湿展剤、分散剤
、固着剤、崩壊剤等をあげることができる。The agrochemical auxiliary agents mentioned herein include carriers (diluents) and other auxiliary agents such as spreading agents, emulsifiers, wetting agents, dispersants, fixing agents, and disintegrants.
液体担体としてはトルエン、キシレン等の芳香族炭化水
素、メタノール、ブタノール、グリコール等のアルコー
ル類、アセトン等のケトン類、ジメチルホルムアミド等
のアミド類、ジメチルスルホキシド等のスルホキシド類
、メチルナ７タレンシクロヘキサン、動植物油、脂肪酸
、脂肪酸エステル等があげられる。Liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol, and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, methylna7talenecyclohexane, animals and plants. Examples include oil, fatty acids, fatty acid esters, etc.
固体担体としてはクレー、カオリン、タルク、珪藻土、
シリカ、炭酸カルシウム、モンモリロナイト、ベントナ
イト、長石、石英、アルミナ、鋸屑等があげられる。Solid carriers include clay, kaolin, talc, diatomaceous earth,
Examples include silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, and sawdust.
また乳化剤または分散剤としては通常界面活性剤が使用
され、たとえば高級アルコール硫酸ナトリウム、ステア
リルトリメチルアンモニウムクロライド、ポリオキシエ
チレンアルキルフェニルエーテル、ラウリルヘタイン等
の陰イオン系界面活性剤、陽イオン系界面活性剤、非イ
オン系界面活性剤、両性イオン系界面活性剤があげられ
る。In addition, surfactants are usually used as emulsifiers or dispersants, such as anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, laurylhetaine, and cationic surfactants. surfactants, nonionic surfactants, and amphoteric surfactants.
展着剤としてはポリオキシエチレンノニルフェニルエー
テル、ポリオキシエチレン５’）リルエーテル等が、湿
展剤としてはポリオキシエチレンノニルフェニルエーテ
ル、ジアルキルスルホサクシネート等が、固着剤として
はカルボキシメチルセルローズ、ポリビニルアルコール
等が、崩壊剤としてはりゲニンスルホン酸ナトリウム、
ラウリル硫酸ナトリウム等があげられる。Spreading agents include polyoxyethylene nonylphenyl ether, polyoxyethylene 5')yl ether, etc. Wetting agents include polyoxyethylene nonylphenyl ether, dialkyl sulfosuccinate, etc., and fixing agents include carboxymethyl cellulose and polyvinyl. Alcohol etc. are used as a disintegrant, and sodium geninsulfonate is used as a disintegrant.
Examples include sodium lauryl sulfate.
いずれの製剤もそのまま単独で使用できるのみならず、
他の農園芸用殺菌剤、殺虫剤、植物生長調節剤、殺ダニ
剤と混合して使用することもできる。Not only can each formulation be used alone, but
It can also be used in combination with other agricultural and horticultural fungicides, insecticides, plant growth regulators, and acaricides.
本発明農園芸用殺虫剤における有効成分化合物含量は、
製剤形態、施用する方法、その他の条件によりて種々異
なり場合によっては有効成分化合物のみでもよいが、通
常は０５〜９５％（重量）好ましくは２〜７０％（１埼
）の範囲である。The active ingredient compound content in the agricultural and horticultural insecticide of the present invention is:
Depending on the formulation form, method of application, and other conditions, only the active ingredient compound may be used in some cases, but it is usually in the range of 05 to 95% (by weight), preferably 2 to 70% (1 volume).
本発明の化合物は茎葉散布、土壌施用いずれの処理方法
においてもイネいもち病、キー否
ウリうどんこ病、などの植物病＼に、すぐれた防除効果
を示し、植物体に薬害などの悪影響を及ぼさない農園芸
用殺菌剤である。The compound of the present invention exhibits excellent control effects on plant diseases such as rice blast and powdery mildew in both foliage and soil applications, and does not have any adverse effects on plants such as phytotoxicity. It is not an agricultural or horticultural fungicide.
以下に実施例をあげて本発明を説明する。 The present invention will be explained below with reference to Examples.
合成例１
ａ） １− （２−（１−（２，４−ジクロルフェニ
ル）−ブトキシ）−エチル−１−イル〕−ＩＨ−１，２
，４−）リアゾール（化合物述４）の製造ニ
ジメチルホルムアミド３０ｍ１．６０％水素化ナトリウ
ム２．０ｇ（０，０４８モル）を含む溶液を攪拌下に、
１．２．４ トリアゾール３．６ｇ（０，０５３モルン
を徐々に添加する。水素のフェニル）−フトキシ〕−エ
チルメタンスルホナート、１６．０ｇ（０，０４４モル
）を滴下する。その後、加熱しながら１１０°〜１２０
′℃で３０分間ないし１時間反応する。ＴＬＣ酢酸エチ
ルで抽出し、酢酸エチル層を水洗し、無水硫酸す） Ｉ
Ｊウムで乾燥する。減圧下に酢酸エチルを濃縮し、残渣
をシリカゲルカラムクロマトで精製すると７．５ｇ（収
率５４．２％）の淡黄色の油状物を得る。Synthesis Example 1 a) 1-(2-(1-(2,4-dichlorophenyl)-butoxy)-ethyl-1-yl]-IH-1,2
, 4-) Preparation of lyazole (compound description 4) 30 ml of dimethylformamide. A solution containing 2.0 g (0,048 mol) of 60% sodium hydride was stirred.
1.2.4 3.6 g (0,053 mol) of triazole are added slowly. 16.0 g (0,044 mol) of hydrogen phenyl)-phthoxy]-ethyl methanesulfonate are added dropwise. Then, while heating,
React for 30 minutes to 1 hour at '°C. TLC Extract with ethyl acetate, wash the ethyl acetate layer with water, and dilute with anhydrous sulfuric acid)
Dry with Jum. Ethyl acetate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 7.5 g (yield 54.2%) of a pale yellow oil.
ｎ ＤＩ−５３４２
ｂ）２．４−ジクロロ−ブチロフェノンの製造＝１．３
−ジクロロベンゼン１００ｇ（０，ロチモル）、塩化ア
ルミニウム１０９ｇ（０，７８６モル）、酪酸クロライ
ド７５ｇ（０，６４モル）を加え徐々に加熱攪拌しなが
ら、９５°〜１０００Ｃで３時間反応する。その後氷水
中に反応物を注ぎ、分離してくる油状物を、ジクロロメ
タンで抽出する。有機溶媒層を５チ重曹水で洗い、無水
硫酸ナトリウムで乾燥後、濃縮する。残渣を減圧下に蒸
留すると１２０゜〜１２２°Ｃ／ ４ ｍＨｇの留分が
１０８．４ｇ（収率７８．０チ）得られる。n DI-5342 b) Production of 2.4-dichloro-butyrophenone = 1.3
- Add 100 g (0, mol) of dichlorobenzene, 109 g (0,786 mol) of aluminum chloride, and 75 g (0,64 mol) of butyric acid chloride, and react at 95° to 1000 C for 3 hours while gradually heating and stirring. Thereafter, the reaction mixture is poured into ice water, and the oily substance that separates is extracted with dichloromethane. The organic solvent layer is washed with 50% sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated. The residue was distilled under reduced pressure to obtain 108.4 g (yield: 78.0 cm) of a fraction having a temperature of 120° to 122°C/4 mHg.
ｃ）１−（２，４−ジクロロフェニル）−ブタノールの
製造：
２．４−ジクロロブチロフェノン１３．０ｇ（０，０６
モル）、エタノール８０ｍ１に、水素化ホウ素ナトリウ
ム２．４ｇ（０，０６モル）を加え還流攪拌下に２時間
反応する。冷却後、氷水中に反応液を注ぎ、分離してく
るオイル分を酢酸エチルで抽出する。酢酸エチル層を水
洗し、無水硫酸ナトリウムで乾燥し溶媒を濃縮すると無
色の油状物１３．２ｇ（収率１００％）の高純度品を得
る。c) Production of 1-(2,4-dichlorophenyl)-butanol: 13.0 g of 2,4-dichlorobutyrophenone (0,06
mol), 2.4 g (0.06 mol) of sodium borohydride was added to 80 ml of ethanol, and the mixture was reacted for 2 hours under reflux and stirring. After cooling, pour the reaction mixture into ice water and extract the oil that separates with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was concentrated to obtain 13.2 g (100% yield) of a colorless oil with high purity.
ｄ） エチル−１−１：１−（２，４−ジクロロフェニ
ル）−ブトキシ〕−アセテートの製造ニジメチルホルム
アミド１００ ｍｌ中に、６０チ水素化ナトリウム２．
９ｇ（０，０７２モル）を懸濁させ、１−（２，４−ジ
クロロフェニル）−ブタノール１３．２ｇ（０，０６モ
ル）を滴下する。更に沃化ナトリウム０，２ｇを加え、
室温下でモノクロル酢酸エチル８．９ ｇ （０，０７
２モル）を滴下、徐々に加熱しながら、８００Ｃで２時
間反応する。反応液を５％重曹水に注ぎ、酢酸エチルで
抽出する。酢酸エチル層糾水洗し、無水硫酸す） ＩＪ
ウムで乾燥後濃縮し、残渣をシリカゲルカラムクロマト
により精製することにより、１７．０ ｇ（収率９３％
）の無色の油状物を得る。d) Preparation of ethyl-1-1:1-(2,4-dichlorophenyl)-butoxy]-acetate In 100 ml of dimethylformamide, 60 ml of sodium thihydride are added.
9 g (0.072 mol) are suspended and 13.2 g (0.06 mol) of 1-(2,4-dichlorophenyl)-butanol are added dropwise. Furthermore, add 0.2 g of sodium iodide,
8.9 g (0.07 g) of monochloroethyl acetate at room temperature
2 mol) was added dropwise, and the mixture was reacted at 800C for 2 hours while gradually heating. The reaction solution was poured into 5% aqueous sodium bicarbonate and extracted with ethyl acetate. Drain the ethyl acetate layer, wash with water, and add anhydrous sulfuric acid)
The residue was purified by silica gel column chromatography to obtain 17.0 g (yield 93%).
) to obtain a colorless oil.
ｅ） ２−（１−（２，４−ジクロロフェニル）−プ
トキシ〕−エタノールの製造：
テトラハイドロフラン３（Ｉｌ、 リチウムアルミニウ
ムハイトムイド２．４ ｇ （０，０６モル）を懸濁さ
せた中に、エチル−１−（ｌ−（２，４−ジクロロフェ
ニル）−ブトキシクーアセテート１７．０ｇ （０，０
５６モル）を含むテトラハイドロフラン溶液１００ ｍ
ｌを氷−塩冷却下に５°〜１０°Ｃを保ちながら１時間
で滴下する。その後室温で１時間、５００Ｃで１時間、
加熱攪拌したのち洸冷却し、氷水中に注ぐ。分離した油
状物を酢酸エチルで抽出し、水洗と無水硫酸す） ＩＪ
ウムで乾燥後濃縮すると、無色の油状物１．４．１ ｇ
（収率９５．７チ）を得る。e) Preparation of 2-(1-(2,4-dichlorophenyl)-ptoxy]-ethanol: Tetrahydrofuran 3(Il, in a suspension of 2.4 g (0.06 mol) of lithium aluminum hytomoid) , 17.0 g of ethyl-1-(l-(2,4-dichlorophenyl)-butoxycuacetate (0,0
100 m of tetrahydrofuran solution containing 56 mol)
1 was added dropwise over 1 hour while maintaining the temperature between 5° and 10° C. under ice-salt cooling. Then at room temperature for 1 hour, at 500C for 1 hour,
After heating and stirring, cool and pour into ice water. The separated oil was extracted with ethyl acetate, washed with water and anhydrous sulfuric acid)
After drying with water and concentrating, 1.4.1 g of a colorless oil
(Yield: 95.7 cm).
ｆ） ２−〔１−（２，４−ジクロロフェニル）−ブ
トキシ〕エチルメタンスルホネートの製造：ベンゼン８
０ｍ１中に、２−１ｌ−（２，４−ジクロロフェニル）
ブトキシ〕エタノール１４．１ｇ（０，０５４モル）、
メタンスルホニルクロライド６．５ｇ（０，０５７モル
）を加え攪拌しながら、氷−塩冷却下にトリエチルアミ
ン６．０ ｇ （０，０６モル）を滴下する。室温で３
０分間、その後６０°〜７０°Ｃで３時間反応し、反応
溶液を冷却し、５％重曹水洗注ぐ。ベンゼン層を分液し
、水洗を行な℃・無水硫酸ナトリウムで乾燥後、濃縮す
る。f) Production of 2-[1-(2,4-dichlorophenyl)-butoxy]ethyl methanesulfonate: Benzene 8
2-1l-(2,4-dichlorophenyl) in 0ml
butoxy]ethanol 14.1 g (0,054 mol),
6.5 g (0.057 mol) of methanesulfonyl chloride was added, and while stirring, 6.0 g (0.06 mol) of triethylamine was added dropwise under ice-salt cooling. 3 at room temperature
0 minutes, then react at 60° to 70°C for 3 hours, cool the reaction solution, and pour in a 5% sodium bicarbonate water wash. Separate the benzene layer, wash with water, dry over anhydrous sodium sulfate at °C, and concentrate.
残渣をシリカゲルカラムクロマトで精製スると１６．０
ｇ（収率ｓ ９．６ ％ ）の無色の油状物を得る。When the residue was purified by silica gel column chromatography, it was 16.0
g (yield s 9.6%) of a colorless oil is obtained.
合成例２
ａ） １−（２−（２，６−シメチルフエノキシ）ペ
ンチル−１−イル） ＩＨ−１，２，４トリアゾール（
化合装置２９）の製造ニ
ジメチルホルムアミド３ Ｑ ｍｌ、６０％水素化ナト
リウム２．１ｇ（０，０５３モル）を含む溶液を攪拌中
に、１．２．４− トリアゾール３．６ｇ（０，０５２
モル）を徐々に添加する。Synthesis Example 2 a) 1-(2-(2,6-dimethylphenoxy)pentyl-1-yl) IH-1,2,4triazole(
Preparation of compounding apparatus 29) While stirring a solution containing 3 Q ml of dimethylformamide and 2.1 g (0,053 mol) of 60% sodium hydride, 3.6 g (0,052 mol) of 1.2.4-triazole was added.
mol) gradually.
水素の発生が止んだのち、２−（２，６−シメチルフエ
ノキシ）ペンチルメタンスルホネート１０．０ｇ（０，
０３５モル）を滴Ｆする。After the hydrogen evolution stopped, 10.0 g of 2-(2,6-dimethylphenoxy)pentyl methanesulfonate (0,
035 mol) was added dropwise.
その後加熱しながら、１１０°〜１２０°Ｃで１時間反
応したのちに冷却し、５％重曹水に注ぎ、分離したオイ
ル分を酢酸エチルで抽出する。酢酸エチル層を水洗し、
無水硫酸ナトリウムで乾燥したのちに濃縮する。Thereafter, the reaction mixture was heated at 110° to 120°C for 1 hour, then cooled, poured into 5% sodium bicarbonate solution, and the separated oil was extracted with ethyl acetate. Wash the ethyl acetate layer with water,
After drying with anhydrous sodium sulfate, concentrate.
残渣をシリカゲルカラムクロマトでＷＩＭすることによ
り、５．５ｇ（収率６０．８係）の白色結晶を得る。ｍ
、ｐ、３９°〜４０°Ｃｂ） メチル−α−（２，６
−シメチルフエノキシ）ペンタネートの製造ニ
ジメチルホルムアミド１５０ ｍｌに水酸化カリウム１
９ｇ（０，２９Ｍ）を溶解した後に、メチル−α−ブロ
モペンタネート５６．５ｇ（０，２９モル）を滴下する
。室温で１時間攪拌し４０°〜４５℃で２時間反応を行
ない、水中に反応液を注ぐ。分離した油状物を酢酸エチ
ルで抽出し、５％−水酸化ナトリウム水溶液で洗浄後、
水洗する。酢酸エチル層を無水硫酸ナトリウムで乾燥し
、濃縮すると６３．６ｇ（収率９３係）の無色油状物を
得る。The residue was subjected to WIM using silica gel column chromatography to obtain 5.5 g (yield: 60.8%) of white crystals. m
, p, 39°~40°Cb) Methyl-α-(2,6
-Preparation of dimethylphenoxy)pentanate 150 ml of dimethylformamide and 1 part of potassium hydroxide
After dissolving 9 g (0.29 M), 56.5 g (0.29 mol) of methyl-α-bromopentanate are added dropwise. Stir at room temperature for 1 hour, react at 40° to 45°C for 2 hours, and pour the reaction solution into water. The separated oil was extracted with ethyl acetate, washed with 5% aqueous sodium hydroxide solution,
Wash with water. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated to obtain 63.6 g (yield: 93%) of a colorless oil.
Ｃ） ２−（２，６−シメチルフエノキシ）ペンタノ
ールの製造：
テトラヒドロフラン１００ｍＪ、 リチウムアルミニ
ウムハイドライド３．８ｇ（０，１モル）を懸濁させた
中に、メチル−α−（２，６−シメチルフエノキシ）ペ
ンタネート２３６ｇ（０１モル）を含むテトラハイド口
フラン溶液１００ ｍｌを氷−塩冷却下に５°〜１０℃
に保ちながら、３０分間で滴下する。さらに室温１時間
、７０°〜８０℃で１時間加熱攪拌したのちに、冷却し
水中に注ぎ、分離する油状物を酢酸エチルで抽出する。C) Production of 2-(2,6-dimethylphenoxy)pentanol: Methyl-α-(2, 100 ml of a tetrahydrofuran solution containing 236 g (0.1 mol) of 6-dimethylphenoxy) pentanate was heated at 5° to 10° C. under ice-salt cooling.
Add the solution dropwise over 30 minutes while maintaining the temperature. After further heating and stirring at room temperature for 1 hour and at 70° to 80° C. for 1 hour, the mixture is cooled and poured into water, and the oily substance that separates is extracted with ethyl acetate.
酢酸エチル層を水洗し、無水硫酸ナトリウムで乾燥後、
濃縮すると無色の油状物１９．６ｇ（収率９４．１係）
を得る。ｎ２５１．５０５５ｄ） ２− （２，６−
シメチルフエノキシ）ペンチルメタンスルホネートの製
造ニ
アセトニトリル１００ ｍｌ中に２−（２，６−シメチ
ルフエノキシ）ペンタノール２０．８ｇ（０，１−Ｆｓ
ル）、メタンスルホニルクロライド１１．５ｇ（０，１
モル）を加え、攪拌しながら、ピリジン７．９ｇ（０，
１モル）を０°〜５℃で滴下する。室温で３０分間、４
０°〜５０’Ｃ２時間加熱攪拌後、反応溶液を冷却し５
チ一重曹水に注ぎ、分離してくる油状物をペンゼ／で抽
出する。ベンゼン層を水洗し無水硫酸ナトリウムで乾燥
後、濃縮すると無色の油状物が得られ、これをシリカゲ
ルクロマトで精製することにより、無色の油状物３４．
０ｇ（収率８９．Ｏ係）を得る。After washing the ethyl acetate layer with water and drying with anhydrous sodium sulfate,
When concentrated, 19.6 g of colorless oil (yield: 94.1%)
get. n251.5055d) 2- (2,6-
Preparation of dimethylphenoxy)pentyl methanesulfonate 20.8 g of 2-(2,6-dimethylphenoxy)pentanol (0,1-Fs
), methanesulfonyl chloride 11.5g (0,1
mol) and while stirring, add 7.9 g of pyridine (0, mol).
1 mol) was added dropwise at 0° to 5°C. 30 minutes at room temperature, 4
After heating and stirring for 2 hours at 0° to 50'C, the reaction solution was cooled to 5
Pour into a solution of sodium bicarbonate and extract the oily substance that separates with Penze. The benzene layer is washed with water, dried over anhydrous sodium sulfate, and then concentrated to obtain a colorless oil, which is purified using silica gel chromatography to obtain a colorless oil.
0 g (yield: 89.0) was obtained.
ｎ Ｄｌ、 ５０３１
合成例１〜２の方法により、さらに本発明化合物が合成
された。n Dl, 5031 The compound of the present invention was further synthesized by the method of Synthesis Examples 1 and 2.
それらの代表的なものを第１表に示す。Representative ones are shown in Table 1.
第 １ 表
以下に製剤例を示すが、農薬補助剤の種色および混合比
率はこれらのみに限定されろことなく、広い範囲で使用
可能である。なお「部Ｊとあるのは１重量部」を意味す
る。Formulation examples are shown below in Table 1, but the seed color and mixing ratio of the agricultural chemical adjuvant are not limited to these, and can be used in a wide range. Note that "Part J" means 1 part by weight.
製剤例１ 粉剤
化合物１２ １−（２−＋ １−（２，４−ジクロルフ
ェニル）−エトキシ）−プロピル−１−イル〕−ＩＨ−
イミダゾール２部とホワイトカーボン１部およびクレー
９７部を混合粉砕し、粉剤とする。Formulation Example 1 Powder Compound 12 1-(2-+ 1-(2,4-dichlorophenyl)-ethoxy)-propyl-1-yl]-IH-
2 parts of imidazole, 1 part of white carbon, and 97 parts of clay are mixed and ground to form a powder.
製剤例２ 水和剤
化合物２９ ｔ−（２−（２，６−シメチルフエノキ
シ）ペンチル−１−イル） −ＩＨ−１，２，４−トリ
アゾール２０部とホワイトカーボン２０部と珪藻土５５
部と高級アルコール硫酸ナトリウム３部およびリグニン
スルホン酸ナトリウム２部とを混合粉砕し水和剤とする
。Formulation Example 2 Wettable powder compound 29 t-(2-(2,6-dimethylphenoxy)pentyl-1-yl)-IH-1,2,4-triazole 20 parts, white carbon 20 parts, diatomaceous earth 55
1 part, 3 parts of higher alcohol sodium sulfate, and 2 parts of sodium lignin sulfonate are mixed and ground to prepare a wettable powder.
製剤例３ 粒剤
化合物２６ １−（２−（２，４−ジクロルフェノキシ
）ペンチル−１−イル）−ＩＨ−１，２，４た後、水１
８部を加え、均等に湿潤させ、次に射出成形機を通して
押し出し、造粒し、整粒機で整粒した後、乾燥し粒径０
．６ ａ〜１＋ｔｍの粒剤とする。Formulation Example 3 Granule compound 26 1-(2-(2,4-dichlorophenoxy)pentyl-1-yl)-IH-1,2,4, then 1 part water
Add 8 parts, moisten it evenly, extrude it through an injection molding machine, granulate it, size it with a sizing machine, and dry it to a particle size of 0.
．． 6 A to 1+tm granules.
製剤例４ 乳剤
化合物４ １−［：２−（１−（２，４−ジクロルフェ
ニル）−フ）＊シ）−エチル−１−イル） −１Ｈ−１
，２，４−）リアゾール ３０部をキシレン５２部に溶
解し、これにアルキルフェノールエチレンオキシド縮合
物とアルキルベンゼンスルホン酸カルシウムノ混合物（
８：２）１８部を混合溶解して乳剤とする。Formulation Example 4 Emulsion Compound 4 1-[:2-(1-(2,4-dichlorophenyl)-f)*c)-ethyl-1-yl) -1H-1
, 2,4-) lyazole was dissolved in 52 parts of xylene, and a mixture of alkylphenol ethylene oxide condensate and calcium alkylbenzenesulfonate (
Mix and dissolve 18 parts of 8:2) to form an emulsion.
本則は水で薄めて、乳濁液として使用する。The basic rule is to dilute it with water and use it as an emulsion.
次に本発明の化合物が各種の農園芸用作物病害に対しす
ぐれた防除効果を有していることを実験例により説明す
る。Next, it will be explained by experimental examples that the compound of the present invention has an excellent control effect on various agricultural and horticultural crop diseases.
実験例１ イネいもち病防除試験（茎葉散布）たて１１
ｃｒｎ、よこ１０ｃｒｎ、高さ１０（７７＋１０プラス
チツク製のポットに２週間、イネ（品種：埼玉もち１０
号）を生育させ、このイネに製剤例２の方法で作成した
本発明化合物を有効成分とする水和剤を希釈して得た所
定濃度の薬液を茎葉散布した。風乾後、イネいもち ゛
病菌（Ｐｙｒｉｃｕｌａｒｉａ ｏｒｙｚａｅ ）の胞
子懸濁液を噴霧接種し、２３℃の温室に２日間保った後
、温室内で発病させ、接種１０日後に発病程度を調査し
、防除価を算出した。結果は第２表の通りである。なお
対照薬剤としてＩＢＰ乳剤（有効成分：Ｓ−ベンジルジ
イソプロビルホスホロチオレートンを用いた。Experimental example 1 Rice blast control test (spraying on foliage) Freshly prepared 11
crn, width 10 crn, height 10 (77 + 10) Rice (variety: Saitama mochi 10) was grown in a plastic pot for 2 weeks.
No.) was grown, and a medicinal solution of a predetermined concentration obtained by diluting a wettable powder containing the compound of the present invention as an active ingredient prepared by the method of Formulation Example 2 was sprayed on the foliage of the rice. After air-drying, a spore suspension of rice blast fungus (Pyricularia oryzae) was spray inoculated, kept in a greenhouse at 23°C for 2 days, allowed to develop in the greenhouse, and 10 days after inoculation, the degree of disease onset was investigated and the control value was determined. was calculated. The results are shown in Table 2. As a control drug, an IBP emulsion (active ingredient: S-benzyldiisoprobyl phosphorothioletone) was used.
０：病斑が全く認められな（・。0: No lesions observed at all (・.
１：病斑がわずかに認められる。1: Slight lesions are observed.
２：病斑が多数認められる。2: Many lesions are observed.
４：枯死葉が多く認められる。4: Many dead leaves are observed.
５：枯死葉がきわめて多く認め られる。5: Very many dead leaves observed It will be done.
無処理区の発病程度−処理区の発病程度第２表 イネい
もち病防除試験（茎葉散布）実験例２ イネいもち病防
除試験（土壌施用）たて１１譚、よこ５ｃｒｎ１高さ１
０ｃｒｎのプラスチック製のポットに２週間イネ（品種
：埼玉もち１０号）を生育させ、このイネに製剤例３の
方法で作成した本発明化合物を有効成分とする粒剤を所
定量土壌施用し、５日後にイネいもち病菌（Ｐｙｒｉｃ
ｕｌａｒｉａ ｏｒｙｚａｅ）の胞子懸濁液を噴霧接種
し、２３℃の温室に２日間保った後、温室内で発病させ
、接種１０日後に発病程度を調査し、防除価を算出した
。結果は第３表の通りである。なお対照薬剤としてＩＢ
Ｐ粒剤（有効成分＝８−ベンジルジイソプロビルホスホ
ロチオレート）を用いた。Incidence level in untreated area - Incidence level in treated area Table 2 Rice blast control test (spraying on foliage) Experiment example 2 Rice blast control test (soil application) 11 plots vertically, 5 crn 1 height 1 horizontally
Rice (variety: Saitama Mochi No. 10) was grown in a 0 crn plastic pot for two weeks, and a predetermined amount of granules containing the compound of the present invention as an active ingredient prepared by the method of Formulation Example 3 was applied to the soil, Five days later, rice blast fungus (Pyric
A spore suspension of ularia oryzae) was spray inoculated, kept in a greenhouse at 23° C. for 2 days, and then allowed to develop in the greenhouse. Ten days after inoculation, the degree of disease onset was investigated and the control value was calculated. The results are shown in Table 3. In addition, IB was used as a control drug.
P granules (active ingredient = 8-benzyldiisoprobyl phosphorothiolate) were used.
０：病斑が全く認められない。0: No lesions observed at all.
１：病斑がわずかに認められる。1: Slight lesions are observed.
２：病斑が多数認められる。2: Many lesions are observed.
４：枯死葉が多く認められる。4: Many dead leaves are observed.
５：枯死葉がきわめて多（認め られる。5: Extremely large number of dead leaves (obviously It will be done.
無処理区の発病程度
第３表 イネいもち病防除試験（土壌施用）実験例３
キュウリうどんこ病防除試験製剤例５で作成した本発明
化合物を有効成分とする乳剤を水で希釈し、第１本葉の
展開期の鉢植えのキュウリ（品種二Ｆ１強カグリーン節
成）に散布し、風乾後キュウリうどんこ病菌（Ｓｐｈａ
ｅｒｏｔｈｅｃａ ｆｕｌｉｇｉｎｅａ ）の胞子を接
種し、温室内に置き、２週間後に発病程度を調査し、防
除価を算出した。対照薬剤としてチオ７アネートメチル
７０％水和剤（有効成分：１，２−ビス（３−メトキシ
カルボニル−２−チオウレイド）ベンゼン）を用いた。Disease severity in untreated area Table 3 Rice blast control test (soil application) Experimental example 3
Cucumber Powdery Mildew Control Test The emulsion containing the compound of the present invention as an active ingredient prepared in Preparation Example 5 was diluted with water and sprayed on potted cucumbers (variety 2F1 strong kagreen nodules) in the stage of first true leaf development. After air-drying, cucumber powdery mildew fungus (Spha)
erotheca fuliginea) and placed in a greenhouse. Two weeks later, the degree of disease onset was investigated and the control value was calculated. As a control drug, thio7anatemethyl 70% hydrating agent (active ingredient: 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene) was used.
結果は第４表の通りである。発病指数、防除価は次のよ
うに算出した。The results are shown in Table 4. The disease index and control value were calculated as follows.
（ＡＸ３）＋（ＢＸ２）＋（ＣＸＩ）
発病指数＝ Ｘ １０１（
Ａ＋１３＋ｃ＋ｐ）ｘａ
Ａ：発病が激しい株数
Ｂ：発病がかなり認められる株
数
Ｃ：発病が縦機な株数
Ｄ：健全株数
無処理区の発病指数(AX3) + (BX2) + (CXI) Incidence index = X 101 (
A+13+c+p)xa A: Number of plants with severe disease onset B: Number of plants with severe disease onset C: Number of stocks with vertical disease onset D: Number of healthy plants Disease index of untreated plot
Claims (2)
アルキル基又はハロゲン原子で置換されたフェニル基を
示し、Ｒ＿２は水素原子又は低級アルキル基を示す。ｎ
は１または２の整数を示し、ｍは０又は１の整数を示す
。Ａｚはピラゾリル基、イミダゾリル基又は１，２，４
−トリアゾリル基を示す）で表わされるＮ−置換アゾー
ル誘導体。(1) Formula▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R represents a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, and R_1 is substituted with a hydrogen atom, a lower alkyl group, or a halogen atom. represents a phenyl group, and R_2 represents a hydrogen atom or a lower alkyl group.n
represents an integer of 1 or 2, and m represents an integer of 0 or 1. Az is a pyrazolyl group, an imidazolyl group, or 1,2,4
- an N-substituted azole derivative represented by (representing a triazolyl group).
アルキル基又はハロゲン原子で置換されたフェニル基を
示し、Ｒ＿２は水素原子又は低級アルキル基を示す。ｎ
は１または２の整数を示し、ｍは０又は１の整数を示す
。Ａｚはピラゾリル基、イミダゾリル基又は１，２，４
−トリアゾリル基を示す）で表わされるＮ−置換アゾー
ル誘導体を有効成分とする農園芸用殺菌組成物。(2) Formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) (In the formula, R represents a hydrogen atom, halogen atom, methyl group, or methoxy group, and R_1 is substituted with a hydrogen atom, lower alkyl group, or halogen atom. represents a phenyl group, and R_2 represents a hydrogen atom or a lower alkyl group.n
represents an integer of 1 or 2, and m represents an integer of 0 or 1. Az is a pyrazolyl group, an imidazolyl group, or 1,2,4
An agricultural and horticultural fungicidal composition comprising an N-substituted azole derivative represented by -triazolyl group) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2299886A JPS62181263A (en) | 1986-02-06 | 1986-02-06 | N-substituted azole derivative and fungicidal composition for agricultural and horticultural use containing said derivative as active component |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2299886A JPS62181263A (en) | 1986-02-06 | 1986-02-06 | N-substituted azole derivative and fungicidal composition for agricultural and horticultural use containing said derivative as active component |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62181263A true JPS62181263A (en) | 1987-08-08 |
Family
ID=12098188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2299886A Pending JPS62181263A (en) | 1986-02-06 | 1986-02-06 | N-substituted azole derivative and fungicidal composition for agricultural and horticultural use containing said derivative as active component |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62181263A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103304394A (en) * | 2013-06-18 | 2013-09-18 | 姜堰市科研精细化工有限公司 | Synthetic method of 2,4-dichlorobenzene butanone |
-
1986
- 1986-02-06 JP JP2299886A patent/JPS62181263A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103304394A (en) * | 2013-06-18 | 2013-09-18 | 姜堰市科研精细化工有限公司 | Synthetic method of 2,4-dichlorobenzene butanone |
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