JPS63239267A - 4(1h)-pyridinone derivative and fungicide for agricultural and horticultural purposes - Google Patents
4(1h)-pyridinone derivative and fungicide for agricultural and horticultural purposesInfo
- Publication number
- JPS63239267A JPS63239267A JP7363587A JP7363587A JPS63239267A JP S63239267 A JPS63239267 A JP S63239267A JP 7363587 A JP7363587 A JP 7363587A JP 7363587 A JP7363587 A JP 7363587A JP S63239267 A JPS63239267 A JP S63239267A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- integer
- acid
- reaction
- 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
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 12
- 239000000417 fungicide Substances 0.000 title claims abstract description 12
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical class OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 title claims abstract 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 31
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- 241000209094 Oryza Species 0.000 abstract description 14
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 13
- 235000009566 rice Nutrition 0.000 abstract description 13
- 240000008067 Cucumis sativus Species 0.000 abstract description 9
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- SPRSAKGTDXVEOA-UHFFFAOYSA-N 1,5-diphenylpentane-2,3,4-trione Chemical class C=1C=CC=CC=1CC(=O)C(=O)C(=O)CC1=CC=CC=C1 SPRSAKGTDXVEOA-UHFFFAOYSA-N 0.000 abstract description 4
- 241001465754 Metazoa Species 0.000 abstract description 2
- 241000233679 Peronosporaceae Species 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000001228 spectrum Methods 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 241000251468 Actinopterygii Species 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000003898 horticulture Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- -1 re Species 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- 238000007605 air drying Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical class CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000006806 disease prevention Effects 0.000 description 2
- 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 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- MLNVBUQTXITYPT-VAWYXSNFSA-N (e)-1,5-diphenylpent-4-ene-1,3-dione Chemical class C=1C=CC=CC=1/C=C/C(=O)CC(=O)C1=CC=CC=C1 MLNVBUQTXITYPT-VAWYXSNFSA-N 0.000 description 1
- GRGOBDJHERORKV-UHFFFAOYSA-N 1,2-diphenylethanimine Chemical class C=1C=CC=CC=1C(=N)CC1=CC=CC=C1 GRGOBDJHERORKV-UHFFFAOYSA-N 0.000 description 1
- YNFWTLXJAGKJRB-UHFFFAOYSA-N 1-phenylethanimine Chemical compound CC(=N)C1=CC=CC=C1 YNFWTLXJAGKJRB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- GRNDXOGZORGERT-UHFFFAOYSA-N 3-oxopent-4-enal Chemical class C=CC(=O)CC=O GRNDXOGZORGERT-UHFFFAOYSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000219193 Brassicaceae Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 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
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 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
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NPZZPCCCUNCARE-UHFFFAOYSA-N ethyl 2-(2-fluorophenyl)propanoate Chemical compound CCOC(=O)C(C)c1ccccc1F NPZZPCCCUNCARE-UHFFFAOYSA-N 0.000 description 1
- ACJOYTKWHPEIHW-UHFFFAOYSA-N ethyl 3-phenylprop-2-ynoate Chemical compound CCOC(=O)C#CC1=CC=CC=C1 ACJOYTKWHPEIHW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 150000004658 ketimines Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- QAFJIJWLEBLXHH-UHFFFAOYSA-N methyl 2-fluorobenzoate Chemical compound COC(=O)C1=CC=CC=C1F QAFJIJWLEBLXHH-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
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- 239000000178 monomer Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- MVDYEFQVZNBPPH-UHFFFAOYSA-N pentane-2,3,4-trione Chemical class CC(=O)C(=O)C(C)=O MVDYEFQVZNBPPH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000014102 seafood Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 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
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- 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、４（ＬＨ）−ビリジノン誘導体及びこれを含
有するａｍ芸用殺菌剤に関するのである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a 4(LH)-viridinone derivative and an am horticultural fungicide containing the same.
（従来の技術）
シンセティック コミュニケーション（Ｓｙｎｔｈａｔ
ｉｃＣｏｓｕ＋ｕｎｉｃａｔｉｏｎｓ） １３（５）４
１１−４１７（１９８３）には、ケチミンとエチルフェ
ニルプロピオレートとの反応により、１，２．６−）−
リフェニルα換４（ＩＨ）−ビリジノン誘導体を製造す
る方法について記載されており、種々の化合物が例示さ
れている。また、特開昭５６−６５８７１号明細書には
１−（Ｉｉ２換フェニル）−２，６−シメチルー４（Ｉ
Ｈ）−ビリジノン誘導体が記載され、これらがキュウリ
うどんこ病に有効であるとともにスライムコントロール
剤としても有用である旨の記載がある。同じく特開昭５
５−１０２５０４号明細書には２，６−ジフェニル−４
（ＬＨ）−ビリジノンが記載され、稲いもち病及びキュ
ウリ炭痕病に有効である旨の記載がある。更に特公昭６
０−３５０号及び６０−３５１号明細書には３−ａ換フ
ェニル又は３．５−Ｉｉ！換フェニル−４−ビリジノン
誘導体が記載されているが、除草剤としての活用を有す
るものであり、殺菌作用については何ら記載されていな
い。(Conventional technology) Synthetic communication
icCosu+unications) 13(5)4
11-417 (1983), the reaction of ketimine with ethylphenyl propiolate produces 1,2.6-)-
A method for producing liphenyl α-substituted 4(IH)-viridinone derivatives is described, and various compounds are exemplified. Furthermore, in JP-A-56-65871, 1-(Ii2-substituted phenyl)-2,6-cymethyl-4(Ii
H)-viridinone derivatives are described, and it is stated that these are effective against cucumber powdery mildew and are also useful as slime control agents. Also published in 1975
5-102504 specifies 2,6-diphenyl-4
(LH)-Viridinone is described and is said to be effective against rice blast and cucumber charcoal stain. In addition, special public relations show 6
0-350 and 60-351, 3-a-substituted phenyl or 3.5-Ii! Although phenyl-4-viridinone derivatives are described, they have utility as herbicides, and nothing is described about their bactericidal action.
（発明が解決しようとする問題点）
シンセティック コミユニケージ１ンには、これらの化
合物がどのような生物活性を有するかについて全く記載
されていない０本発明者らは、新規で前記明細書に記載
された化合物より更に有用なａＩＩ芸ｍ殺菌剤を開発す
るため、１，２．６−）−リフェニル置換−４−ビリジ
ノン骨格に着目し鋭意研究を重ねた結果、本発明化合物
の脅威に成功し、かつ５園芸用殺菌剤としてすぐれた効
果を有するものであることを見出し本発明を完成した。(Problems to be Solved by the Invention) Synthetic Comics 1 does not describe at all what kind of biological activity these compounds have. In order to develop a more useful aII fungicide than the compounds previously used, we focused on the 1,2,6-)-riphenyl-substituted-4-viridinone skeleton and conducted intensive research, and as a result, we succeeded in addressing the threat of the compound of the present invention. The present invention was completed based on the discovery that it has excellent effects as a horticultural fungicide.
（問題点を解決するための手段）
本発明の４（ＩＨ）−ビリジノン誘導体は一般式
〔式中Ｘはハロゲン原子、アルコキシ基またはニトロ基
を示し、ｙ、ｚは同一または相異なり水ｌｓ原子、ハロ
ゲン原子、アルキル基、アルコキシ基またはニド・０基
を示し、０〜３の整数を示す、但し、ｙ、ｚが同時に水
：Ｍ原子を示す時はｎは２以上の整数を示す、〕で表さ
れる。(Means for Solving the Problems) The 4(IH)-pyridinone derivative of the present invention has the general formula: , represents a halogen atom, an alkyl group, an alkoxy group, or a nido-0 group, and represents an integer of 0 to 3; however, when y and z simultaneously represent a water:M atom, n represents an integer of 2 or more.] It is expressed as
また、本発明化合物は塩を形成することができる。Furthermore, the compounds of the present invention can form salts.
更に２本発明化合物は次のような互変異性体をとる。Furthermore, two compounds of the present invention have the following tautomers.
一般式（りにて表される本発明化合物を第１表に例示す
る。化合物番号は以後の記載において参照される。Compounds of the present invention represented by the general formula (R) are illustrated in Table 1. Compound numbers will be referred to in the following description.
第 １表 次に本発明の化合物の製造法について説明する。Table 1 Next, a method for producing the compound of the present invention will be explained.
（イ）本発明化合物は
一般式
（式中、Ｙ及びＺは前記と同一の意味を示す、）で示さ
れる１、５−ジフェニルペンタントリオン誘導体または
その互変異性体と一般式
（一般式Ｙ及びｎは前記と同一の意味を示す、）で示さ
れるアニリン誘導体とを反応させることによって製造す
ることができる。(a) The compound of the present invention is a 1,5-diphenylpentantrione derivative represented by the general formula (wherein Y and Z have the same meanings as above) or a tautomer thereof, and a 1,5-diphenylpentantrione derivative represented by the general formula (in the general formula Y and n has the same meaning as above).
ここで示された化合物（Ｕ）の互変異性体は次の一般式
で表されるものである。The tautomer of compound (U) shown here is represented by the following general formula.
以下余白
一般式（■）で表されるトリオン誇導体は５一般に１−
ベンゾイルアセトン誘導体を安息香酸エステル誘導体と
適当な溶媒、例えばテトラヒドロフラン、ジエチルエー
テル、ジメトキシエタン等の中で、水素化ナトリウムま
たはナトリウムメチラートのような塩基を加え縮合する
ことによって製造することができる。The trion pride conductor represented by the general formula (■) below is 5 generally 1-
Benzoylacetone derivatives can be prepared by condensation of benzoate ester derivatives in a suitable solvent such as tetrahydrofuran, diethyl ether, dimethoxyethane, etc. with the addition of a base such as sodium hydride or sodium methylate.
例えば１−ベンゾイル−アセトンと２−フルオロ安息香
酸メチルエステルから、１−フェニル−５−（２−フル
オロフェニル）ペンタン−１，３，５−トリオンを製造
することができ、１−（２−フルオロベンゾイル）アセ
トンと安息香酸メチルエステルから、１−（２−フルオ
ロフェニル）−５−フェニルペンタン−１，３，５−）
−リオンを１１造することができる。For example, 1-phenyl-5-(2-fluorophenyl)pentane-1,3,5-trione can be produced from 1-benzoyl-acetone and 2-fluorobenzoic acid methyl ester; 1-(2-fluorophenyl)-5-phenylpentane-1,3,5-) from benzoyl)acetone and benzoic acid methyl ester
- You can build 11 Lions.
ここで得られた一般式（■）で示されるペンタントリオ
ン誘導体またはその互変異性体と一般式（ＩＩＩ）で示
されるアニリン誘導体との反応は、一般に適当な溶媒１
例えば、ベンゼン、トルエン、キシレン等の炭化水素類
、クロロベンゼン、塩化メチレン、クロロホルム等のハ
ロゲン化炭化水素類、ジイソフロビルエーテル、テトラ
ヒドロフラン、ジオキサン等のエーテル類、アセトン、
メチルエチルケトン、シクロヘキサノン等のケトン類、
酢酸エチル等のエステル類、アセトニトリル等のニトリ
ル類、Ｎ、Ｎ−ジメチルホルムアミド、Ｎ、Ｎ−ジメチ
ルアセトアミド、Ｎ−メチルピロリドン等のアミド類、
更には、ジメチルスルホキシド、酢酸等の存在下または
非存在下で行い、好ましくは、キシレンまたはクロロベ
ンゼンに溶解して反応させる。この場合、適当な反応助
剤を加えて反応させることもできる。使用する反応助剤
として、適当な酸１例えば、硫酸、塩酸等の鉱酸、Ｐ−
トルエンスルホン酸、トリフルオロメタンスルホン酸等
の有機酸、三フッ化ホウ素、塩化アルミニウム、四塩化
チタン等のルイス酸をあげることができ、更には、生成
してきた水をディーンスタークトラップにて補集するこ
とにより反応させることができる。The reaction of the pentantrione derivative represented by the general formula (■) obtained here or its tautomer with the aniline derivative represented by the general formula (III) is generally carried out using an appropriate solvent 1
For example, hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as chlorobenzene, methylene chloride, and chloroform, ethers such as diisofurovir ether, tetrahydrofuran, and dioxane, acetone,
Ketones such as methyl ethyl ketone and cyclohexanone,
Esters such as ethyl acetate, nitriles such as acetonitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone,
Furthermore, the reaction is carried out in the presence or absence of dimethyl sulfoxide, acetic acid, etc., preferably by dissolving in xylene or chlorobenzene. In this case, the reaction may be carried out by adding a suitable reaction aid. As reaction aids used, suitable acids such as mineral acids such as sulfuric acid and hydrochloric acid, P-
Examples include organic acids such as toluenesulfonic acid and trifluoromethanesulfonic acid, and Lewis acids such as boron trifluoride, aluminum chloride, and titanium tetrachloride.Furthermore, the generated water is collected in a Dean-Stark trap. The reaction can be carried out by
また、使用する酸と溶媒に応じてモレキュラーシーブス
のような脱水剤の存在下に反応させることもできる。The reaction can also be carried out in the presence of a dehydrating agent such as molecular sieves depending on the acid and solvent used.
例えば、ジメチルスルホキシド中、Ｐ−トルエンスルホ
ン酸を使用する場合には、モレキュラーシーブス５Ａが
使用できる。モレキュラーシーブスの使用量は１通常。For example, when using P-toluenesulfonic acid in dimethylsulfoxide, molecular sieves 5A can be used. The amount of molecular sieves used is usually 1.
１．５−ジフェニルペンタントリオン誘導体（ＩＩ）の
０゜１モルに対して、２〜２００ｇの範囲で使用される
が。It is used in an amount of 2 to 200 g per 0.1 mole of 1,5-diphenylpentantrione derivative (II).
好ましくは、５０〜２００ｇで反応させることができる
。Preferably, the reaction can be carried out in 50 to 200 g.
反応は、溶媒の凝固点から沸点の任意の温度、好ましく
は、１０℃から溶媒の沸点までの温度で行うことができ
る。The reaction can be carried out at any temperature from the freezing point to the boiling point of the solvent, preferably from 10° C. to the boiling point of the solvent.
反応終了後は、酸またはモレキュラーシーブスを水及び
アルカリ溶液で洗浄するかろ過等により除去し、反応生
成物をクロロホルムで抽出したのち、溶媒を留去すれば
、本発明化合物をｍ造することができる。必要ならば。After the reaction is completed, the acid or molecular sieves are removed by washing with water and an alkaline solution or by filtration, the reaction product is extracted with chloroform, and the solvent is distilled off, thereby producing the compound of the present invention. can. If necessary.
アセトン、メタノール、エタノール、ベンゼン、トルエ
ン、ジイソプロピルエーテル、酢酸エチル、クロロホル
ム、ヘキサン等で再結晶することにより、またはシリカ
ゲルカラムクロマトグラフィーにより精製することがで
きる。It can be purified by recrystallization from acetone, methanol, ethanol, benzene, toluene, diisopropyl ether, ethyl acetate, chloroform, hexane, etc., or by silica gel column chromatography.
（ロ）本発明化合物は
一般式
（式中、ｘ、ｙ、ｚ及びｎは前記と同一の意味を示す、
）または、一般式
（式中、ｘ、ｙ、ｚ及びｎは前記と同一の意味を示す、
）で示される５−７ニリノー１．５−ジフェニル−４−
ペンテン−１，３−ジオン誘導体またはこれらの互変異
性体を触媒の存在下閉環させることによって製造するこ
とができる。(b) The compound of the present invention has the general formula (where x, y, z and n have the same meanings as above,
) or the general formula (where x, y, z and n have the same meanings as above,
) 5-7nilino1,5-diphenyl-4-
It can be produced by ring-closing pentene-1,3-dione derivatives or their tautomers in the presence of a catalyst.
１二で示した化合物（ＴＶ）の互変異性体は５次の一般
式で表されるものである。The tautomer of the compound (TV) shown in 12 is represented by the following 5-order general formula.
以下余白
↑↓ ↑↓
↑↓ ↑↓ ｅ
だ
↑↓ ↑↓
↑↓ ↑↓
この場合、一般式（ｒＶ）及び（Ｖ）で示される５−７
ニリノー１．５−ジフェニル−４−ペンテン−１，３−
ジオン誘導体またはこれらの互変異性体を適当な溶媒、
例えば、ベンゼン、トルエン、キシレン等の炭化水素類
。Below margin ↑↓ ↑↓ ↑↓ ↑↓ e ↑↓ ↑↓ ↑↓ ↑↓ In this case, 5-7 shown by general formulas (rV) and (V)
Nilino 1,5-diphenyl-4-pentene-1,3-
dione derivatives or their tautomers in a suitable solvent,
For example, hydrocarbons such as benzene, toluene, and xylene.
クロロベンゼン、塩化メチレン、クロロホルム等のハロ
ゲン化炭化水ａｍ、ジイソプロピルエーテル、テトラヒ
ドロフラン、ジオキサン等のエーテル類、アセトン、メ
チルエチルケトン等のケトン類、アセトニトリル等のニ
トリルｉ１１． Ｎ、Ｎ−ジメチルホルムアミド、Ｎ、
Ｎ−ジメチルアセトアミド等のアミド類、更には、ジメ
チルスルホキシド、酢酸等に溶解もしくはＩ！ｌ？Ｉｉ
するか、または無溶媒で反応を行なう、酸触媒としては
１例えば、ポリリン酸、硫酸、ｐ−トルエンスルホン酸
、塩化アルミニウムなどが挙げられる６反応は溶媒の凝
固点から沸点までの温度、好ましくは１０℃から溶媒の
沸点までの温度で行うことができる。Halogenated hydrocarbons am such as chlorobenzene, methylene chloride and chloroform, ethers such as diisopropyl ether, tetrahydrofuran and dioxane, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile i11. N, N-dimethylformamide, N,
Amides such as N-dimethylacetamide, dimethyl sulfoxide, acetic acid, etc. or I! l? Ii
Examples of acid catalysts include polyphosphoric acid, sulfuric acid, p-toluenesulfonic acid, aluminum chloride, etc. 6 The reaction is carried out at a temperature from the freezing point to the boiling point of the solvent, preferably 10 It can be carried out at temperatures ranging from °C to the boiling point of the solvent.
反応終了後は１反応液に氷水を加えクロロホルムで抽出
し、水洗、乾燥後溶媒を留去すれば本発明化合物を製造
することができる。必要ならば、ベンゼン、トルエン、
メタノール、クロロホルム、酢酸エチル、アセトン、ヘ
キサン等で再結晶することにより、またはシリカゲルカ
ラムクロマトグラフィーにより精製することができる。After completion of the reaction, the compound of the present invention can be produced by adding ice water to one reaction solution, extracting with chloroform, washing with water, drying, and then distilling off the solvent. If necessary, benzene, toluene,
It can be purified by recrystallization with methanol, chloroform, ethyl acetate, acetone, hexane, etc., or by silica gel column chromatography.
（ハ）更に零ｇ！明化合物は、一般式
（式中、Ｚは前記と同一の意味を示す、）で示されるフ
ェニルプロピン酸エステル誘導体と一般式（式中、Ｘ、
Ｙ及びｎは前記と同一の意味を示す、）で示されるＮ−
フェニル−１−フェニルエタンイミン誘導体とを塩化ア
ルミニウム、四塩化チタン、三フッ化ホウ素、三塩化ホ
ウ素等のルイス酸の存在下で反応させることによって製
造することができる。(c) Even more zero g! The bright compound is a phenylpropynic acid ester derivative represented by the general formula (wherein, Z has the same meaning as above) and a phenylpropynic acid ester derivative represented by the general formula (wherein, X,
Y and n have the same meanings as above, N-
It can be produced by reacting a phenyl-1-phenylethanimine derivative with a Lewis acid such as aluminum chloride, titanium tetrachloride, boron trifluoride, or boron trichloride.
この場合、一般式（ＶＩ）で示されるプロピン酸エステ
ル誘導体と一般式（■）で示されるＮ−フェニル−１−
フェニルエタンイミン諺導体を適当な溶媒９例えば、ベ
ンゼン、トルエン、キシレン、クロロベンゼン、ジメチ
ルスルホキシド等に溶解もしくは懸濁させるか、または
無溶媒で、好ましくは、トルエンに溶解して１反応助剤
として０．５〜５当量のルイス酸を加える。ルイス酸と
しては、好ましくは、１当量の塩化アルミニウムを加え
反応終了後、硫酸水溶液、水、更にアルカリ水溶液で洗
浄し、クロロホルムで抽出後、乾燥し、溶媒を留去すれ
ば本発明化合物を製造することができる。必要ならば。In this case, a propynic acid ester derivative represented by general formula (VI) and N-phenyl-1- represented by general formula (■) are used.
The phenylethanimine conductor is dissolved or suspended in a suitable solvent 9, such as benzene, toluene, xylene, chlorobenzene, dimethyl sulfoxide, etc., or without a solvent, preferably in toluene, as a reaction aid. Add .5 to 5 equivalents of Lewis acid. As the Lewis acid, preferably, 1 equivalent of aluminum chloride is added, and after the reaction is completed, the compound of the present invention is produced by washing with an aqueous sulfuric acid solution, water, and then an aqueous alkali solution, extracting with chloroform, drying, and distilling off the solvent. can do. If necessary.
シリカゲルカラムクロマ１−タグラフイーを通し、更に
アセトン、メタノール、ベンゼン、酢酸エチル、クロロ
ホルム等で再結晶することにより精製することができる
。It can be purified by passing it through silica gel column chroma 1-tagraphy and further recrystallizing with acetone, methanol, benzene, ethyl acetate, chloroform, etc.
（ニ）更に本発明化合物は、ケミッシェ ベリヒテ（Ｃ
ｈａｍ Ｂａｒ） ４４．３６４８ （１９１１）あ
るいは特開昭５６−６５８７１号明細書等に記載の方法
に準じても！ｌＩ造することができる。(d) Furthermore, the compound of the present invention is a compound of the present invention.
ham Bar) 44.3648 (1911) or according to the method described in JP-A-56-65871. II can be constructed.
即ち、一般式
（式中、Ｙ及びＺは前記と同一の意味を示す、）で示さ
れるデヒドロベンゾイル酢酸誘導体と一般式（式中、Ｘ
及びｎは前記と同一の意味を示す、）で示されるアニリ
ン誘導体とを適当な溶媒の存在下、少量の酸の存在下に
反応させることによっても製造することができる。That is, a dehydrobenzoyl acetic acid derivative represented by the general formula (wherein Y and Z have the same meanings as above) and a dehydrobenzoyl acetic acid derivative represented by the general formula (wherein, X
It can also be produced by reacting aniline derivatives represented by (and n has the same meaning as above) in the presence of a small amount of acid in the presence of an appropriate solvent.
この場合適当な溶媒として例えば、ベンゼン、トルエン
、キシレン、クロロベンゼン、エチルアルコールあるい
はジメトキシエタン等が挙げられる。酸としては塩酸、
硫酸あるいはパラトルエンスルホン酸等が挙げられる。In this case, suitable solvents include, for example, benzene, toluene, xylene, chlorobenzene, ethyl alcohol or dimethoxyethane. The acid is hydrochloric acid,
Examples include sulfuric acid and para-toluenesulfonic acid.
また、前記一般式（■）で示される化合物としては例え
ば、デヒドロベンゾイル酢酸、デヒドロ（２−クロロベ
ンゾイル）酢酸、デヒドロ（２−フルオロベンゾイル）
酢酸、デヒドロ（２−二トロベンゾイル）酢酸等を挙げ
ることができる。In addition, examples of the compound represented by the general formula (■) include dehydrobenzoyl acetic acid, dehydro(2-chlorobenzoyl)acetic acid, dehydro(2-fluorobenzoyl)
Examples include acetic acid, dehydro(2-nitrobenzoyl)acetic acid, and the like.
次に実施例を挙げて１本発明化合物の製造方法を説明す
る。Next, a method for producing one of the compounds of the present invention will be explained with reference to Examples.
実施例 １
■−（２−クロロ−５−メトキシフェニル）−２−（２
−フルオロフェニル）−６−フェニル−４（ＩＨ）−ビ
リジノン（化合物１７）の合成
Ｎ−（２−クロロ−５−メトキシフェニル）−１−フェ
ニルエタンイミン７．７ｇと塩化アルミニウム４．７ｇ
及び２−フルオロフェニルプロピオン酸エチルエステル
５゜８ｇをトルエン３００ｍΩに懸濁させＳ時間還流し
た。Example 1 ■-(2-chloro-5-methoxyphenyl)-2-(2
Synthesis of N-(2-chloro-5-methoxyphenyl)-1-phenylethanimine and 4.7 g of aluminum chloride
and 5.8 g of 2-fluorophenylpropionic acid ethyl ester were suspended in 300 mΩ of toluene and refluxed for S hours.
その後１反応液を氷冷した２規定硫酸５００ ｍ Ａに
注ぎ。Thereafter, one reaction solution was poured into ice-cooled 2N sulfuric acid at 500 mA.
クロロホルム抽出を行い、有機層を水洗した後、硫酸ナ
トリウムで乾燥した。ろ通抜１ｗ１媒を留去し、残渣を
シリカゲルクロマトグラフィーを用い、ｎ−ヘキサン：
酢酸エチル＝１：１の混合溶媒で展開溶出した。溶媒留
去ご、アセトンより再結晶して１．９ｇの１−（２−ク
ロロ−５−メトキシフェニル）−２−（２−フルオロフ
ェニル）−６−フェニル−４（ＩＨ）−ビリジノンを得
た。After performing chloroform extraction and washing the organic layer with water, it was dried over sodium sulfate. The 1w1 medium was distilled off, and the residue was subjected to silica gel chromatography using n-hexane:
The mixture was developed and eluted with a mixed solvent of ethyl acetate=1:1. The solvent was distilled off and recrystallized from acetone to obtain 1.9 g of 1-(2-chloro-5-methoxyphenyl)-2-(2-fluorophenyl)-6-phenyl-4(IH)-pyridinone. .
融点は２０２〜２０４℃であった。The melting point was 202-204°C.
実施例 ２
２−（２−クロロフェニル）−１−（３−ニトロフェニ
ル）−６−フェニル−４（ＬＨ）−ビリジノン（化合物
７）の合成
ニー（２−クロロフェニル）−５−フェニル−１，３，
５−ペンタトリオン３．１ｇと３−ニトロアニリン２．
１ｇをキシレン３００ｍ１１に溶解し、更にＰ−Ｆ−ル
エンスルホン酸２，９ｇ及びモレキュラーシーブス５Ａ
１０ｇを加えた。ディーンスターク装置を付して２時間
還流した後、反応液から固形物をろ別した。ろ液にクロ
ロホルムを加え、１０％塩酸溶液１５０ｍ１１及び１０
％水酸化ナトリウム溶液１５０ｍＱで洗浄し更に水洗し
た後、硫酸ナトリウムで乾燥した。乾燥剤をろ別後、溶
媒を留去した。残渣はシリカゲルカラムクロマトグラフ
ィーを用い。Example 2 Synthesis of 2-(2-chlorophenyl)-1-(3-nitrophenyl)-6-phenyl-4(LH)-viridinone (compound 7) Ni(2-chlorophenyl)-5-phenyl-1,3 ，
3.1 g of 5-pentatrione and 2.3-nitroaniline.
Dissolve 1 g in 300 ml of xylene, and further add 2.9 g of P-F-luenesulfonic acid and 5A molecular sieves.
10g was added. After refluxing for 2 hours using a Dean-Stark apparatus, solid matter was filtered off from the reaction solution. Add chloroform to the filtrate and add 150ml of 10% hydrochloric acid solution
After washing with 150 mQ of % sodium hydroxide solution and further washing with water, it was dried over sodium sulfate. After filtering off the desiccant, the solvent was distilled off. The residue was analyzed using silica gel column chromatography.
ｎ−ヘキサン：酢酸エチル＝１＝１の混合溶媒で展開溶
出した。溶媒留去後得られた結晶をアセトンより再・結
晶すると０．６ｇの２−（２−クロロフェニル）−１−
（３二トロフェニル）−６−フェニル−４（ＩＨ）−ビ
リジノンを得た。The mixture was developed and eluted with a mixed solvent of n-hexane:ethyl acetate=1=1. When the crystals obtained after evaporation of the solvent were recrystallized from acetone, 0.6 g of 2-(2-chlorophenyl)-1-
(3nitrophenyl)-6-phenyl-4(IH)-pyridinone was obtained.
融点は２７９〜２８０℃であった。The melting point was 279-280°C.
実施例 ３
２．６−ビス（２−フルオロフェニル）−１−（３，５
−ジメトキシフェニル）−４−（ＬＨ）−ビリジノン（
化合物２）の合成
デヒドロ（２−フルオロベンゾイル）酢酸３．３ｇと３
゜５−ジメトキシアニリン１．５ｇをキシレン１００ｍ
Ｍに溶解した。この反応液に少量の塩醜を加えて８時間
還流した１反応後、減圧下で溶媒を留去し、残渣をクロ
ロホルムで抽出した。この抽出液を水洗し、１０％塩酸
溶液１００ ｍ （１及び１０％水酸化ナトリウム溶液
液１００ｍｍで洗浄し再び水洗した後、硫酸ナトリウム
で乾燥した。＠燐剤をろ別後、溶媒を留去した。残液は
シリカゲルカラムクロマトグラフィーを用い、酢酸エチ
ルによりＦＡＩした。得られた結晶をアセトンヤ再結晶
し、０．５ｇの２，６−ビス（２−フルオロフェニル）
−１−（３，５−ジメトキシフェニル）−４−（ＩＨ）
−ビリジノンを得た。Example 3 2.6-bis(2-fluorophenyl)-1-(3,5
-dimethoxyphenyl)-4-(LH)-viridinone (
Synthesis of compound 2) 3.3 g of dehydro(2-fluorobenzoyl)acetic acid and 3
゜1.5g of 5-dimethoxyaniline in 100m of xylene
Dissolved in M. After one reaction in which a small amount of salt was added to this reaction solution and refluxed for 8 hours, the solvent was distilled off under reduced pressure, and the residue was extracted with chloroform. This extract was washed with water, washed with 100 ml of 10% hydrochloric acid solution (100 ml of 1 and 10% sodium hydroxide solution, washed with water again, and dried over sodium sulfate. After filtering off the phosphorus agent, the solvent was distilled off. The residual liquid was subjected to FAI with ethyl acetate using silica gel column chromatography. The obtained crystals were recrystallized with acetonate, and 0.5 g of 2,6-bis(2-fluorophenyl)
-1-(3,5-dimethoxyphenyl)-4-(IH)
-Viridinone was obtained.
融点は２３２〜２３３℃であった。The melting point was 232-233°C.
本発明のｒｓｍ芸用膜用殺菌剤本発明化合物それ自体で
用いてもよいが１通常は担体、界面活性剤１分散剤又は
補助剤などを配合して常法により、例えば粉剤、水和剤
。The rsm artistic film disinfectant of the present invention may be used as the compound of the present invention, but it is usually formulated with a carrier, a surfactant, a dispersant, or an auxiliary agent, etc., in a conventional manner, such as a powder or a wettable powder. .
乳剤、微粒剤に製剤して泪いられる。It can be formulated into emulsions and fine granules.
好適な担体としては１例えばタルク、ベントナイト、ク
レー、カオリン、珪藻土、ホワイトカーボン、バーミキ
ュライト、消石灰、ケイ砂、硫安、尿素などの固体担体
、イソプロピルアルコール、キシレン、シクロヘキサン
、メチルナフタレンなどの液体担体などが挙げられる。Suitable carriers include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexane, and methylnaphthalene. Can be mentioned.
界面活性剤及び分散剤としては１例えばアルコール硫酸
エステル塩、アルキルアリールスルホン酸塩、リグニン
スルホン酸塩、ジアリールメタンジスルホン酸塩、ポリ
オキシエチレングリコールエーテル、ポリオキシエチレ
ンアルキルアリールエーテル、ポリオキシエチレンソル
ビタンモノアルキレートなどが挙げられる。補助剤とし
ては５例えばカルボキシメチルセルロース、ポリエチレ
ングリコール、アラビアゴムなどが挙げられる。これら
の製剤は適宜な濃度に希釈して散布するか、又は直接施
用する。Examples of surfactants and dispersants include alcohol sulfate salts, alkylaryl sulfonates, lignin sulfonates, diarylmethane disulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, and polyoxyethylene sorbitan monomers. Examples include alkylate. Examples of adjuvants include carboxymethylcellulose, polyethylene glycol, gum arabic, and the like. These preparations can be diluted to an appropriate concentration and sprayed, or applied directly.
有効成分の配合割合については、必要に応じ適宜選ばれ
るが、粉剤又は粒剤とする場合は０．１〜２０％（重量
）、乳剤又は水和剤とする場合は５〜８０％（重量）が
適当である。The blending ratio of the active ingredient is selected as appropriate, but it is 0.1 to 20% (by weight) for powders or granules, and 5 to 80% (by weight) for emulsions or wettable powders. is appropriate.
本発明の農園芸用殺菌剤の施用量は、使用される化合物
の種類、対象病害１発生傾向、被害の程度、環境条件。The application amount of the agricultural and horticultural fungicide of the present invention depends on the type of compound used, the tendency of the target disease to occur, the degree of damage, and the environmental conditions.
使用する剤型などによって変動するが、粉剤及び粒剤の
ようにそのまま使用する場合は有効成分として１０アー
ル当り０．１〜５−好ましくは、１ｇ〜１ｋｇのＩｌＩ
囲から適宜に選ぶのがよい、又、乳剤あるいは水和剤の
ように最終的に液状で使用する場合は、０．１〜１０，
０００ Ｐｐｍ、好ましくは１０〜３０００ｐｐｍの範
囲から適宜に選ぶのがよい。Although it varies depending on the dosage form used, when used as is, such as powders and granules, the active ingredient is 0.1 to 5 - preferably 1 g to 1 kg of IlI per 10 ares.
It is best to select an appropriate amount from the range below. Also, when used in a final liquid form such as an emulsion or a wettable powder, it is 0.1 to 10.
000 ppm, preferably selected from the range of 10 to 3000 ppm.
本発明化合物にはけ他の殺菌剤、殺虫剤を混合して使用
することができる。The compound of the present invention can be used in combination with other fungicides and insecticides.
殺虫剤としては、０，０−ジメチル ０−（３，５，６
−ドリクロロー２−ピリジル）ホスホロチオニー）−、
０，０−ジエチル ０−（３，５，６−ドリクロロー２
−ピリジル）ホスホロチオエート、０−（２−クロロ−
１−（２，４゜５−トリクロロフェニル）ビニル〕 ０
，０−ジメチルホスフェート、０−（２−クロロ−１−
（２，４，５−トリクロロフェニル）ビニル〕 ０．Ｏ
−ジメチルホスフェート、０．０−ジメチル Ｓ−［（
５−メトキシ−１，３，４−チアジアゾール）−２（３
Ｈ）オニル−（３）−メチル］ジチオホスフェート、
４．４ ’−ジクロロベンジル酸エチル。As an insecticide, 0,0-dimethyl 0-(3,5,6
-Dolichloro2-pyridyl)phosphorothiony)-,
0,0-diethyl 0-(3,5,6-dolichloro2
-pyridyl)phosphorothioate, 0-(2-chloro-
1-(2,4゜5-trichlorophenyl)vinyl〕 0
, 0-dimethyl phosphate, 0-(2-chloro-1-
(2,4,5-trichlorophenyl)vinyl] 0. O
-dimethyl phosphate, 0.0-dimethyl S-[(
5-methoxy-1,3,4-thiadiazole)-2(3
H) onyl-(3)-methyl]dithiophosphate,
4.4'-Ethyl dichlorobenzylate.
４．４′−ジクロロベンジル酸イソプロピル、エチル０
−ベンゾイル−３−クロロ−２，６−シメトキシベンゾ
ヒドロキシメート、パラクロロフェニルパラクロロベン
ゼン、水酸化トリシクロヘキシルスズ等が挙げられる。4.4'-Isopropyl dichlorobenzilate, ethyl 0
-benzoyl-3-chloro-2,6-simethoxybenzohydroxymate, parachlorophenylparachlorobenzene, tricyclohexyltin hydroxide, and the like.
殺菌剤としては、１．２−ビス（メトキシカルボニル−
２−チオウレイド）ベンゼン、１，４−ビス（２，２，
，２−トリクロロ−１−ホルムアミドエチル）ピペラジ
ン、５−メチル−１，２，４−トリアゾロ（３，４−ｂ
）ベンゾチアゾール、アルミニウムトリスエチルホスホ
ナート。As a fungicide, 1,2-bis(methoxycarbonyl-
2-Thioureido)benzene, 1,4-bis(2,2,
, 2-trichloro-1-formamidoethyl)piperazine, 5-methyl-1,2,4-triazolo(3,4-b
) Benzothiazole, aluminum trisethylphosphonate.
１．１′−イミニオジ（オクタメチレン）ジグアニジニ
ウムトリアセテート、 １，２，５．Ｇ−テトラヒド
ロ−４Ｈ−ピロロ（３，２１１−ｉｌ ｊ）キノリン−
４−オン、メチルＮ−（２−メトキシアセチル）−Ｎ−
（２，６−キシリル）−ＤＬ−アラニナート等が挙げら
れる。1.1'-Iminiodi(octamethylene)diguanidinium triacetate, 1,2,5. G-tetrahydro-4H-pyrrolo(3,211-il j)quinoline-
4-one, methyl N-(2-methoxyacetyl)-N-
(2,6-xylyl)-DL-alaninate and the like.
次に本発明のａｍ芸用殺菌剤の実施例を挙げて具体的に
説明する。下記実施例中の％は重量を意味する。Next, examples of the am fungicidal fungicide of the present invention will be specifically explained. In the examples below, % means weight.
実施例 ４（粉 剤）
化合物（１）２％、珪藻±５％及びクレー９３％を均一
に混合粉砕して粉剤とした。Example 4 (Powder) 2% of compound (1), ±5% of diatoms, and 93% of clay were uniformly mixed and ground to obtain a powder.
実施例 ５（水和剤）
化合物（２）５０％、珪藻±４５％、ジナフチルメタン
ジスルホン酸ナトリウム２％及びリグニンスルホン酸ナ
トリウム３％を均一に混合粉砕して水和剤とした。Example 5 (Wettable powder) Compound (2) 50%, diatom ±45%, sodium dinaphthylmethane disulfonate 2% and sodium ligninsulfonate 3% were uniformly mixed and ground to prepare a wettable powder.
実施例 ６（乳 剤）
化合物（３）３０％、シクロへキサノン２０％、ボリオ
キシエチレンアルキルアリールエーテル１１％、アルキ
ルベンセンスルホン酸カルシウム４％及びメチルナフタ
リン３５％を均一に溶解して乳剤とした。Example 6 (Emulsion) An emulsion was prepared by uniformly dissolving 30% of compound (3), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbensene sulfonate, and 35% of methylnaphthalene. .
実施例 ７（粒 剤）
化合物（４）５％、ラウリルアルコール硫酸エステルの
ナトリウム塩２％、リグニンスルホン酸ナトリウム５％
、カルボキシメチルセルロース２％及びクレー８６％を
均一に混合粉砕する。この混合物に水２０％を加えて練
合し、押出式造粒機を用いて１４〜３２メツシユの粒状
に加工したのち、乾燥して粒剤とした。Example 7 (granules) Compound (4) 5%, sodium salt of lauryl alcohol sulfate 2%, sodium lignin sulfonate 5%
, 2% carboxymethylcellulose and 86% clay are uniformly mixed and ground. This mixture was kneaded with 20% water, processed into 14 to 32 mesh granules using an extrusion granulator, and dried to form granules.
（発明の効果）
本発明のａ園芸用殺菌剤は、稲紋枯病、稲いもち病、キ
ュウリベと病、キュウリうどんこ病、キュウリ灰色かび
病、小松菜黒すす病等の水稲及び園芸関係の病害に幅広
い抗菌スペクトラムを有するものであるが、特に稲紋枯
病防除剤として卓効を示すものである。この活性は予防
的にも治療的にも発現し、しかも持続性を有する。更に
、作物、温血動物及び魚介類に対しても安全性が高い等
の優れた特徴を有するものである。(Effects of the Invention) The horticultural fungicide of the present invention is effective against paddy rice and horticultural diseases such as rice sheath blight, rice blast, cucumber downy mildew, cucumber gray mold, and komatsuna black sooty. It has a broad antibacterial spectrum, and is particularly effective as a control agent for rice sheath blight. This activity is expressed both prophylactically and therapeutically, and is long-lasting. Furthermore, it has excellent characteristics such as being highly safe for crops, warm-blooded animals, and seafood.
次に本発明の農園芸用殺菌剤の奏する効果を試験例を挙
げて具体的に説明する。Next, the effects of the agricultural and horticultural fungicide of the present invention will be specifically explained using test examples.
試験例 １ 稲紋枯病予防効果試験
直径７Ｉの素焼体に水稲種子（品種：全南風）を１５粒
づつ播種し、温室内で４〜５週間育成した。第５葉が展
開した稲幼苗に実施例５に準じて調製した水和剤を５０
０ｐｐｍに水で希釈し、１鉢当り１０ｍ１１を散布した
。Test Example 1 Rice sheath blight preventive effect test Fifteen rice seeds (variety: Zennanfu) were sown in each unglazed body with a diameter of 7I, and grown in a greenhouse for 4 to 5 weeks. 50% of a hydrating powder prepared according to Example 5 was applied to rice seedlings with the fifth leaf developed.
It was diluted with water to 0 ppm and sprayed in an amount of 10ml per pot.
風乾後モミガラフスマ培地で７日間培養した紋枯病菌（
Ｒｈｊｚｏｃｔｏｎｉａ ａｏｌａｎｉ）を株元に接
種し、湿室内（２８℃）に置き、５日後に稲葉鞘部分に
形成された病斑の高さを測定し、下記の計算式に従い防
除価を算出した。After air-drying, the sheath blight fungus (
Rhjzoctonia aolani) was inoculated at the base of the plant, placed in a humid room (28°C), and 5 days later, the height of the lesion formed on the rice leaf sheath was measured, and the control value was calculated according to the following formula.
結果を第２表に示す。The results are shown in Table 2.
以下余白
比較薬剤２
■
試験例 ２ 稲いもち病予防効果試験直径９Ｉ３の白
磁製体に籾（品種：愛知層）を２０粒づつ播種し、温室
内で３〜４週間育成した。第４葉が展開した稲幼苗に実
施例５に準じて１ｌＩＲシた水和剤を５００ｐｐｍに水
で希釈し、１体当り１０ｍΩを散布した。風乾後いも病
菌（Ｐｉｒｉｃｕｌａｒｉａ ｏｒｙｚａａ）の胞子
液を噴霧接種し、２５℃の湿室内に入れた。接種５０後
病斑を数え防除価を算出した。Comparison drug 2 below Test example 2 Rice blast preventive effect test 20 grains of paddy (variety: Aichi layer) were sown on a white porcelain body with a diameter of 9I3 and grown in a greenhouse for 3 to 4 weeks. A hydrating powder prepared by applying 1 IR IR according to Example 5 was diluted with water to 500 ppm and sprayed at a dose of 10 mΩ per rice seedling with the fourth leaf developed. After air-drying, a spore solution of Piricularia oryzaa was spray inoculated and placed in a humid chamber at 25°C. After 50 inoculations, the lesions were counted and the control value was calculated.
評価基準
Ａクラス ： 防除価≧９０％
Ｂクラス ： ＃ ７０〜９０％未満Ｃクラス ：
〃 ４０〜７０％未満Ｄクラス ：＃＞４Ｑ％
結果を上記評価基準に従い第３表に示す。Evaluation criteria A class: Control value ≧90% B class: # Less than 70 to 90% C class:
〃 40 to less than 70% D class: #>4Q% The results are shown in Table 3 according to the above evaluation criteria.
尚、比較薬剤は試験例１と同一のものを用いた。Note that the same comparative drug as in Test Example 1 was used.
第 ３ 表
以下余白
試験例 ３ キュウリベと病予防効果試験９ａ１１×
９ａｍの塩化ビニール装体にキュウリ種子（品種：相模
半白）を１２粒づつ播種し、温室内で７日間育成させた
。子葉が展開したキュウリ幼苗に実施例５に準じて調製
した水和剤を５００ｐｐｍに水で希釈し、ｌ体当り１０
ｍＡを散布した。風乾後キュウリベと病菌（Ｐａｓｕｄ
ｏｐｏｒｏｎｏｓｐｏｒａ ｅｕｂａｎｓｉｓ）の胞
子懸濁液を噴ｍ接種し、２０〜２２℃の湿室内に入れた
。接種７日後下記基室により発病程度を調査し発病度及
び防除価を求めた。Table 3 Margin test example 3 Cucumber and disease prevention effect test 9a11×
Twelve cucumber seeds (variety: Sagami Hanshiro) were sown in each 9 am vinyl chloride container and grown in a greenhouse for 7 days. A hydrating agent prepared according to Example 5 was diluted with water to 500 ppm for cucumber seedlings with developed cotyledons, and 10% per 1 seedling was added.
mA was sprayed. After air drying, cucumber and diseased bacteria (Pasud)
The cells were inoculated with a spore suspension of (oporonospora eubansis) and placed in a humid chamber at 20-22°C. Seven days after inoculation, the degree of disease onset was investigated using the following standard, and the disease severity and control value were determined.
発病程度
Ｎ ： 発病が認められない （葉数：ｎ０）小
： 発病面積 ＜ １／３ （葉数：ｎ、
）中 ： ＃ ２／３ 〜 １／
３ （葉数： ｎ２）大 ： 〃 ＞
２／３（葉数： ｎ、）発病度（％）；
Ｎ＝＝ｎ、＋ｎ、＋ｎ、＋ｎ。Disease severity N: No disease onset (Number of leaves: n0) Small: Disease area < 1/3 (Number of leaves: n,
) Medium: # 2/3 ~ 1/
3 (Number of leaves: n2) large: 〃 >
2/3 (Number of leaves: n,) Disease severity (%); N==n, +n, +n, +n.
結果を第４表に示す。The results are shown in Table 4.
尚、比較薬剤は試験例１と同一のものを用いた。Note that the same comparative drug as in Test Example 1 was used.
第４表
試験例 ４ 小松菜黒すす病予防効果試験９ ｃｓ
Ｘ ９ ａｍの塩化ビニール装体に小松菜種子１２粒づ
つ播種し、温室内で７日間育成させた。子葉が展開した
小松菜幼苗に実施例５に準じてｇｌｌＩＩ！シた水和剤
を５００ｐｐｍに水で希釈し、ｌ体当り１０ｍｆｆ１を
散布した。風乾後アブラナ科黒すす病菌（Ａｌｔａｒｎ
ａｒｉａ ｂｒａｓｓｉｃｏｌａ）の胞子ｓ４液を噴
霧接種し、３０℃の湿室内に入れた。Table 4 Test Example 4 Komatsuna black soot disease prevention effect test 9 cs
Twelve komatsuna seeds were sown in each x 9 am vinyl chloride packaging and grown in a greenhouse for 7 days. gllII! according to Example 5 to Komatsuna young seedlings with expanded cotyledons. The wettable powder was diluted with water to 500 ppm and sprayed at 10 mff1 per liter. After air drying, Brassicaceae black sooty fungus (Altarn)
Aria brassicola) spores were inoculated by spraying and placed in a humid chamber at 30°C.
接種３日後に病斑数を数えて一葉当りの平均病半数を求
めて下記計算式により防除価を算出し、評価基準に従い
評価した結果を第５表に示した。Three days after inoculation, the number of lesions was counted to determine the average half of the disease per leaf, and the control value was calculated using the following formula. Table 5 shows the results of evaluation according to the evaluation criteria.
評価基準
−Ａクラス ： 防除価≧９０％
Ｂクラス ： ＃ ７０〜９０％未満Ｃクラス ：
〃 ４ｏ〜７０％未満Ｄクラス ：＃＜４０％
尚、比較薬剤は試験例１と同一のものを用いた。Evaluation criteria - A class: Control value ≧90% B class: # 70 to less than 90% C class:
〃4o~less than 70% D class: #<40% The same comparative drug as in Test Example 1 was used.
第５表Table 5
Claims (2)
を示し、Ｙ、Ｚは同一または相異なり水素原子、ハロゲ
ン原子、アルキル基、アルコキシ基またはニトロ基を示
し、０〜３の整数を示す。但し、Ｙ、Ｚが同時に水素原
子を示す時はｎは２以上の整数を示す。〕で表わされる
４（１Ｈ）−ピリジノン誘導体。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X represents a halogen atom, an alkoxy group, or a nitro group, and Y and Z are the same or different hydrogen atom, halogen atom, alkyl group, or alkoxy group. Alternatively, it represents a nitro group and represents an integer of 0 to 3. However, when Y and Z simultaneously represent hydrogen atoms, n represents an integer of 2 or more. ] A 4(1H)-pyridinone derivative represented by:
を示し、Ｙ、Ｚは同一または相異なり水素原子、ハロゲ
ン原子、アルキル基、アルコキシ基またはニトロ基を示
し、０〜３の整数を示す。但し、Ｙ、Ｚが同時に水素原
子を示す時はｎは２以上の整数を示す。〕で表わされる
４（１Ｈ）−ピリジノン誘導体を有効成分として含有す
る農園芸用殺菌剤。(2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, Alternatively, it represents a nitro group and represents an integer of 0 to 3. However, when Y and Z simultaneously represent hydrogen atoms, n represents an integer of 2 or more. ] An agricultural and horticultural fungicide containing a 4(1H)-pyridinone derivative represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7363587A JPS63239267A (en) | 1987-03-27 | 1987-03-27 | 4(1h)-pyridinone derivative and fungicide for agricultural and horticultural purposes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7363587A JPS63239267A (en) | 1987-03-27 | 1987-03-27 | 4(1h)-pyridinone derivative and fungicide for agricultural and horticultural purposes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63239267A true JPS63239267A (en) | 1988-10-05 |
Family
ID=13523962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7363587A Pending JPS63239267A (en) | 1987-03-27 | 1987-03-27 | 4(1h)-pyridinone derivative and fungicide for agricultural and horticultural purposes |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63239267A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256249A (en) * | 2019-07-11 | 2019-09-20 | 湘潭大学 | A kind of preparation method for the aromatic ketone compounds that β, δ-position different functional groups replace |
-
1987
- 1987-03-27 JP JP7363587A patent/JPS63239267A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256249A (en) * | 2019-07-11 | 2019-09-20 | 湘潭大学 | A kind of preparation method for the aromatic ketone compounds that β, δ-position different functional groups replace |
| CN110256249B (en) * | 2019-07-11 | 2023-06-27 | 湘潭大学 | Preparation method of aromatic ketone compound substituted by beta, delta-position different functional groups |
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