JPH03275675A - Aralkylamine derivative, production thereof and germicide - Google Patents
Aralkylamine derivative, production thereof and germicideInfo
- Publication number
- JPH03275675A JPH03275675A JP2075662A JP7566290A JPH03275675A JP H03275675 A JPH03275675 A JP H03275675A JP 2075662 A JP2075662 A JP 2075662A JP 7566290 A JP7566290 A JP 7566290A JP H03275675 A JPH03275675 A JP H03275675A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- lower alkyl
- acid
- atom
- 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
- 150000003974 aralkylamines Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 230000002070 germicidal effect Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 150000002978 peroxides Chemical class 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 27
- 239000002904 solvent Substances 0.000 abstract description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 7
- 240000008067 Cucumis sativus Species 0.000 abstract description 6
- 241000209140 Triticum Species 0.000 abstract description 6
- 235000021307 Triticum Nutrition 0.000 abstract description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract description 5
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 4
- 241000221785 Erysiphales Species 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 4
- 240000005979 Hordeum vulgare Species 0.000 abstract description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 abstract description 2
- 241000233679 Peronosporaceae Species 0.000 abstract description 2
- 244000052616 bacterial pathogen Species 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 238000003898 horticulture Methods 0.000 abstract description 2
- 241001330975 Magnaporthe oryzae Species 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- -1 etc.) is preferable Chemical group 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000843 powder Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000003902 lesion Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000000887 hydrating effect Effects 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000857 drug effect Effects 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 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 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- BTLKROSJMNFSQZ-UHFFFAOYSA-N 2,4-dichloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(Cl)=N1 BTLKROSJMNFSQZ-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
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- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
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- 239000000460 chlorine Substances 0.000 description 1
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- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
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- 238000004440 column chromatography Methods 0.000 description 1
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- LLTVGKHHDXGLMR-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.OC.ClCCl LLTVGKHHDXGLMR-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 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
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 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
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (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、新規なアラルキルアミン誘導体又はその酸付
加塩、その製造法及びそれを有効成分とする殺菌剤に関
するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel aralkylamine derivative or an acid addition salt thereof, a method for producing the same, and a fungicide containing the same as an active ingredient.
本発明のアラルキルアミン誘導体と類似したものとして
は、例えば、特開昭５９−３６６６６号公報、特開昭６
４−６８３８２号公報などに記載されたものが知られて
おり、また、それらの化合物には殺虫、殺ダニ及び殺菌
活性があることも知られている。Examples of compounds similar to the aralkylamine derivatives of the present invention include JP-A-59-36666 and JP-A-6
Those described in Japanese Patent No. 4-68382 are known, and it is also known that these compounds have insecticidal, acaricidal, and bactericidal activities.
しかし、それらの開示された化合物は、殺虫及び殺ダニ
剤としての効力は強いが、殺菌剤としての効−力は十分
なものとはいえなかった。However, although the disclosed compounds had strong efficacy as insecticides and acaricides, their efficacy as fungicides was not sufficient.
〔発明が解決しようとする問題点］
本発明の目的は、新規なアラルキルアくン誘導体又はそ
の酸付加塩、その製造法及びそれを有効成分とする殺菌
剤を提供することである。[Problems to be Solved by the Invention] An object of the present invention is to provide a novel aralkylaquone derivative or an acid addition salt thereof, a method for producing the same, and a fungicide containing the same as an active ingredient.
〔問題点を解決するための手段］
本発明者らは、前記の問題点を解決するために鋭意研究
した結果、新規なアラルキルアミン誘導体が顕著に改善
された殺菌活性を有することを見出し、本発明を完成す
るに至った。[Means for Solving the Problems] As a result of intensive research to solve the above-mentioned problems, the present inventors discovered that a novel aralkylamine derivative has significantly improved bactericidal activity. The invention was completed.
即ち、本発明は、
（１）次式：
（式中、Ｒ１は水素原子を表し：Ｒｔｌ＝ｔハロゲン原
子を表し：Ｒ１は低級アルキル基を表し；或いは、Ｒｚ
とＲ１とは、それらが結合している炭素原子と共にピリ
ミジン環に縮合して、硫黄原子１個を有していてもよい
飽和又は不飽和の５もしくは６員環を表し；Ｒ４は水素
原子を表し；Ｒ％は低級アルキル基又はシクロアルキル
基を表し；Ｒ８は水素原子を表し；ｍは０．１又は２を
表し；ｎは１を表す、）
で示されるアラルキルアくン誘導体又はその酸付加塩
（２）次式：
（式中、Ｒ２、Ｒ３及びＲ４
であり；Ｘはａ開基を表す。That is, the present invention provides (1) the following formula: (wherein, R1 represents a hydrogen atom: Rtl=t represents a halogen atom; R1 represents a lower alkyl group; or Rz
and R1 represent a saturated or unsaturated 5- or 6-membered ring optionally containing one sulfur atom, fused to the pyrimidine ring together with the carbon atom to which they are bonded; R4 represents a hydrogen atom; Aralkylaquine derivative or its acid addition represented by: R% represents a lower alkyl group or cycloalkyl group; R8 represents a hydrogen atom; m represents 0.1 or 2; n represents 1) Salt (2): (wherein R2, R3 and R4; X represents an a-opening group.
で示される化合物と
次式：
は前記の記載と同義
）
（式中、Ｒ＋ 、Ｒｓ 、Ｒ＆及びｎは前記の記載と同
義である。）
で示される化合物とを反応させて、
次式：
（式中、Ｒ，、Ｒｚ 、Ｒ，、Ｒ，、Ｒ，、Ｒ，及びｎ
は前記の記載と同義である。）
で示される化合物を得、次にこの化合物（■゛）を過酸
化物で酸化することによって、
次式：
（式中、Ｒ，、Ｒ，、Ｒ３、Ｒ４、Ｒ，、Ｒ，及びｎは
前記の記載と同義であり；ｍ゛は１又は２を表す。）
で示される化合物を得ることを特徴とする前記の式（Ｉ
）で示されるアラルキルアミン誘導体又はその酸付加塩
の製造法
（３）前記の式（１）で示されるアラルキルアミン誘導
体又はその酸付加塩を有効成分とする殺菌剤に関するも
のである。A compound represented by the following formula: (in which R+, Rs, R&, and n have the same meanings as described above) is reacted with a compound represented by the following formula: In the formula, R,, Rz, R,, R,, R,, R, and n
is synonymous with the above description. ), and then by oxidizing this compound (■゛) with a peroxide, the following formula: (wherein R,, R,, R3, R4, R,, R, and n is synonymous with the above description; m' represents 1 or 2).
(3) A method for producing an aralkylamine derivative represented by formula (1) or an acid addition salt thereof.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
前記の目的化合物である新規なアラルキルアミン誘導体
（１）（（Ｉ’）及び（■″）〕、その製造原料である
（Ｉ［）及び（Ｉ［［）の化合物において、Ｒ，として
は、水素原子、ハロゲン原子などを挙げることができる
が；好ましくは水素原子がよい。In the novel aralkylamine derivatives (1) ((I') and (■'')) which are the target compounds, and the compounds (I[) and (I[[) which are the raw materials for their production, R is: Examples include a hydrogen atom and a halogen atom; hydrogen atoms are preferred.
Ｒ２としては、水素原子、ハロゲン原子、低級アルキル
基などを挙げることができるが；好ましくはハロゲン原
子（例えば、フッ素原子、塩素原子、臭素原子、ヨウ素
原子など）がよく；さらに好ましくは塩素原子がよい。Examples of R2 include a hydrogen atom, a halogen atom, and a lower alkyl group; preferably a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.); more preferably a chlorine atom. good.
Ｒ３としては、水素原子、ハロゲン原子、低級アルキル
基などを挙げることができるが；好ましくは低級アルキ
ル基（例えば、炭素原子数１〜５の直鎖状又は分岐状の
アルキル基）がよく；さらに好ましくはメチル基、エチ
ル基がよい。Examples of R3 include a hydrogen atom, a halogen atom, and a lower alkyl group; preferably a lower alkyl group (e.g., a linear or branched alkyl group having 1 to 5 carbon atoms); Preferably, a methyl group or an ethyl group is used.
或いは、Ｒ２とＲ３とは、それらが結合している炭素原
子と共にピリミジン環に縮合して、硫黄原子１個を有し
ていてもよい飽和又は不飽和の５もしくは６員環を形成
していてもよいが；好ましくはベンゼン環又はチオフェ
ン環を形成するのがよい。Alternatively, R2 and R3 are fused together with the carbon atom to which they are bonded to a pyrimidine ring to form a saturated or unsaturated 5- or 6-membered ring which may have one sulfur atom. However, it is preferable to form a benzene ring or a thiophene ring.
Ｒ４としては、水素原子、低級アルキル基などを挙げる
ことができるが：好ましくは水素原子がよい。Examples of R4 include a hydrogen atom and a lower alkyl group; preferably a hydrogen atom.
Ｒ１としては、水素原子、低級アルキル基、シクロアル
キル基、ハロ低級アルキル基などを挙げることができる
が；好ましくは低級アルキル基（例えば、炭素原子数１
〜８の直鎖状又は分岐状のアルキル基）、シクロアルキ
ル基（例えば、炭素原子数１〜６のもの）がよく：さら
に好ましくは、低級アルキル基では炭素原子数１〜３の
直鎖状又は分岐状のアルキル基（例えば、メチル基、エ
チル基、イソプロピル基など）がよく、シクロアルキル
基では炭素原子数１〜６のもの（例えば、シクロプロピ
ル基など）がよい。Examples of R1 include a hydrogen atom, a lower alkyl group, a cycloalkyl group, and a halo-lower alkyl group; preferably, a lower alkyl group (for example, one having 1 carbon atom
~8 straight-chain or branched alkyl groups), cycloalkyl groups (e.g., those having 1 to 6 carbon atoms) are preferred; more preferably, lower alkyl groups are straight-chain or branched alkyl groups having 1 to 3 carbon atoms. Alternatively, a branched alkyl group (eg, methyl group, ethyl group, isopropyl group, etc.) is preferable, and a cycloalkyl group having 1 to 6 carbon atoms (eg, cyclopropyl group, etc.) is preferable.
Ｒ４としては、水素原子、ハロゲン原子、低級アルキル
基、低級アルコキシ基、ハロ低級アルキル基などを挙げ
ることができるが；好ましくは水素原子がよい。Examples of R4 include a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, and a halo-lower alkyl group; preferably a hydrogen atom.
ｍは０．１又は２を表す。m represents 0.1 or 2.
ｎは１又は２を表すが、１が好ましい。n represents 1 or 2, preferably 1.
Ｘとしては、特に限定されず、例えぽ、ハロゲン原子（
塩素、臭素又はヨウ素など）、アルキルチオ基（メチル
チオ、エチルチオ、プロピルチオ、ブチルチオなど）、
ハロゲンで置換されていてもよいアルカンスルホニルオ
キシ基（メタンスルホニルオキシ、エタンスルホニルオ
キシ、トリフルオロメタンスルホニルオキシなど）、了
り一ルスルホニルオキシ基（ベンゼンスルホニルオキシ
、Ｐ−トルエンスルホニルオキシなど）、水酸基などを
挙げることができるが、好ましくはハロゲン原子がよく
、さらに好ましくは塩素原子がよい。X is not particularly limited, and examples include halogen atoms (
chlorine, bromine or iodine), alkylthio groups (methylthio, ethylthio, propylthio, butylthio, etc.),
Alkanesulfonyloxy groups that may be substituted with halogen (methanesulfonyloxy, ethanesulfonyloxy, trifluoromethanesulfonyloxy, etc.), phosphorussulfonyloxy groups (benzenesulfonyloxy, P-toluenesulfonyloxy, etc.), hydroxyl groups, etc. Among them, a halogen atom is preferable, and a chlorine atom is more preferable.
３−位、４−位を挙げることができるが、好ましくは４
−位がよい。The 3-position and the 4-position can be mentioned, but preferably the 4-position.
− is better.
目的化合物（Ｉ）は、アミノ基を有しているので容易に
酸付加塩を浴底することができる。Since the target compound (I) has an amino group, an acid addition salt can be easily formed therein.
酸付加塩を形成する酸としては、例えば、無機酸（塩酸
、臭化水素酸、硝酸、硫酸、リン酸など）、カルボン酸
（ギ酸、シュウ酸、フマル酸、アジピン酸、ステアリン
酸、オレイン酸、アコニット酸など）、有機スルホン酸
（メタンスルホン酸、ベンゼンスルホン酸、ｐ−トルエ
ンスルホン酸など）、サッカリンなどを挙げることがで
きる。Examples of acids that form acid addition salts include inorganic acids (hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, etc.), carboxylic acids (formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, etc.). , aconitic acid, etc.), organic sulfonic acids (methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc.), saccharin, and the like.
原料化合物（ＩＩ）において、＊印の炭素原子が不斉炭
素原子であるときには、得られた目的化合物（１）には
、個々の光学異性体、ラセミ化合物又はそれらの混合物
が含まれる。When the carbon atom marked with * in the starting compound (II) is an asymmetric carbon atom, the obtained target compound (1) includes individual optical isomers, racemic compounds, or mixtures thereof.
本発明の目的化合物（Ｉ）（（Ｉ’）及び（■”）〕は
、例えば、次式に示すように行うことによって、製造す
ることができる。The object compound (I) ((I') and (■'')) of the present invention can be produced, for example, by the following formula.
（ｎ） （Ｉ［［） （式中、Ｒ，、Ｒｚ 、Ｒｓ 、Ｒ，、Ｒ，、Ｒ，。(n) (I[[) (In the formula, R,, Rz, Rs, R,, R,, R,.
ｎ及びＸは前記の記載と同義である。）本発明で用いる
原料化合物（ｎ）は、例えば、ジャーナル・オブ・ケミ
カル・ソサイエティ（Ｊ。n and X are as defined above. ) The raw material compound (n) used in the present invention is described, for example, in the Journal of Chemical Society (J.
Ｃ，Ｓ）、３４７８〜３４８１ （１９５５年）に記載
の方法に準じて、次式に示すように行うことによって、
容易に製造することができる。C,S), 3478-3481 (1955), by performing as shown in the following formula,
It can be easily manufactured.
（式中、Ｒ１、Ｒ３及びＲ４は前記の記載と同義である
。）
本発明で用いる原料化合物（Ｉ［［）は、例えば、ジャ
ーナル・オブ・アメリカン・ケミカル・ソサイエティ（
Ｊ、Ａ、Ｃ，Ｓ）、ユニ、１４５５（１９５７年）など
に記載の方法に準じて、次式に示すように行うことによ
って、容易に製造することができる。(In the formula, R1, R3, and R4 have the same meanings as described above.) The raw material compound (I[[) used in the present invention is, for example,
J, A, C, S), Uni, 1455 (1957), etc., and can be easily produced by carrying out the following formula.
（式中、Ｒ，、Ｒ，、Ｒ，及びｎは前記の記載と同義で
ある。）
過酸化物としては、特に限定されず、例えば、過酸化水
素、ｍ−クロロ過安息香酸、メタ過ヨウ素酸ナトリウム
、過マンガン酸カリウム、次亜塩素酸ナトリウムなどが
挙げられる。(In the formula, R, , R, , R, and n have the same meanings as described above.) The peroxide is not particularly limited, and examples thereof include hydrogen peroxide, m-chloroperbenzoic acid, and metaperoxybenzoic acid. Examples include sodium iodate, potassium permanganate, and sodium hypochlorite.
通常、原料化合物（ｎ）と原料化合物（Ｉ［［）とを溶
媒中で塩基存在下に反応させることによって製造するの
が好ましいが、塩基を加えないでも反応させて得ること
ができるし、また、無溶媒で原料化合物の（ＩＩ）と（
Ｉ［［）とを加熱溶解させて反応させることによって得
ることもできる。Usually, it is preferable to produce by reacting starting compound (n) and starting compound (I[[) in a solvent in the presence of a base, but it can also be obtained by reacting without adding a base. , the starting compound (II) and (
It can also be obtained by heating and dissolving and reacting with I[[).
溶媒としては、本反応に直接関与しないものであれば特
に限定されず、例えば、ベンゼン、トルエン、キシレン
、メチルナフタリン、石油エーテル、リグロイン、ヘキ
サン、クロルベンゼン、ジクロルエタン、塩化メチレン
、クロロホルム、ジクロルエタン、トリクロルエチレン
、シクロヘキサンのような塩素化された又はされていな
い芳香族、脂肪族、脂環式の炭化水素類；ジエ、チルエ
ーテル、テトラヒドロフラン、ジオキサンなどのような
エーテル類；アセトン、メチルエチルケトンなどのよう
なケトン類；メタノール、エタノール、エチレングリコ
ールなどのようなアルコール類又はその含水物、Ｎ、Ｎ
−ジメチルホルムアミド、Ｎ、Ｎ−ジメチルアセトアミ
ドなどのようなアミド類ニトリエチルアミン、ピリジン
、Ｎ、 Ｎ−ジエチルアニリンなどのような有機塩基
；１゜３−ジメチル−２−イミダゾリジノン：ジメチル
スルホキシド；前記溶媒の混合物などを挙げることがで
きる。The solvent is not particularly limited as long as it is not directly involved in this reaction, and examples include benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichloroethane, methylene chloride, chloroform, dichloroethane, and trichloro. Chlorinated or non-chlorinated aromatic, aliphatic, cycloaliphatic hydrocarbons such as ethylene, cyclohexane; ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; ketones such as acetone, methyl ethyl ketone, etc. Alcohols such as methanol, ethanol, ethylene glycol, etc. or their hydrates, N, N
- amides such as dimethylformamide, N,N-dimethylacetamide, etc.; organic bases such as nitriethylamine, pyridine, N,N-diethylaniline, etc.; 1.3-dimethyl-2-imidazolidinone: dimethyl sulfoxide; Mixtures of solvents and the like can be mentioned.
塩基としては、例えば、トリエチルアミン、ピリジン、
Ｎ、Ｎ−ジエチルアニリンなどのような有機塩基；ナト
リウムメトキシド、ナトリウムエトキシドなどのような
アルカリ金属アルコキシド類：ナトリウムアミド、水酸
化ナトリウム、水酸化カリウム、炭酸カリウム、炭酸ナ
トリウム、水素化ナトリウムなどの無機塩基などを挙げ
ることができる。そして、反応速度を上げるために、触
媒として４−（Ｎ、Ｎ−ジメチルアミノ）ピリジンを添
加することが好ましい。Examples of the base include triethylamine, pyridine,
Organic bases such as N,N-diethylaniline, etc.; Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, etc.; sodium amide, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydride, etc. Examples include inorganic bases. In order to increase the reaction rate, it is preferable to add 4-(N,N-dimethylamino)pyridine as a catalyst.
反応温度は、特に限定されないが、通常は室温から使用
する溶媒の沸点以下の温度範囲内であり、沸点以下の温
度範囲内で加温することによって反応時間を短縮するこ
とができる。The reaction temperature is not particularly limited, but is usually within a temperature range from room temperature to the boiling point of the solvent used, and the reaction time can be shortened by heating within the temperature range below the boiling point.
反応時間は、前記の濃度、温度によって変化するが、通
常３〜８時間で行うことができる。The reaction time varies depending on the concentration and temperature mentioned above, but it can usually be carried out for 3 to 8 hours.
目的化合物（Ｉ゛）と過酸化物とを溶媒中で反応させる
ことによって、目的化合物（Ｉ”）を製造することがで
きる。The target compound (I'') can be produced by reacting the target compound (I'') with a peroxide in a solvent.
溶媒としては、本反応に直接関与しないものであれば特
に限定されず、例えば、クロロホルム、ジクロロメタン
のような塩素化された脂肪族炭化水素類；メタノール、
エタノールなどのようなアルコール類：アセトン、メチ
ルエチルケトンなどのようなケトン類；テトラヒドロフ
ラン、ジオキサンなどのような環状エーテル類；酢酸、
プロピオン酸のような脂肪族カルボン酸類；水及び前記
溶媒の混合物など、を挙げることができる。The solvent is not particularly limited as long as it is not directly involved in this reaction; for example, chlorinated aliphatic hydrocarbons such as chloroform and dichloromethane; methanol;
Alcohols such as ethanol; ketones such as acetone, methyl ethyl ketone; cyclic ethers such as tetrahydrofuran, dioxane; acetic acid,
Mention may be made of aliphatic carboxylic acids such as propionic acid; mixtures of water and the aforementioned solvents.
化合物（Ｉ”）と過酸化物とを用いる割合は、化合物（
１’）１モル°に対して、過酸化物０．５〜３モルの割
合で加えることがでるが、好ましくは１〜２．２モルが
よい。The ratio of compound (I”) and peroxide to be used is
1') It can be added at a ratio of 0.5 to 3 moles per 1 mole of peroxide, preferably 1 to 2.2 moles.
反応温度は、−１０°Ｃから使用する溶媒の沸点以下の
温度範囲内で行う限り特に限定されないが、通常、−１
０°Ｃ〜室温が好ましい。The reaction temperature is not particularly limited as long as it is carried out within the temperature range from -10°C to the boiling point of the solvent used, but usually -1
0°C to room temperature is preferred.
反応時間は、前記の濃度、温度によって変化するが、通
常１〜８時間で行うことができる。The reaction time varies depending on the concentration and temperature mentioned above, but it can usually be carried out for 1 to 8 hours.
以上のようにして製造された目的化合物（１）（（１”
）及び（Ｉ”）〕は、再結晶、各種クロマトグラフィー
などの公知の手段で適宜精製することができる。Target compound (1) ((1”) produced as above
) and (I'')] can be appropriately purified by known means such as recrystallization and various chromatography.
そして、その酸付加塩は、例えば、反応終了後の反応液
中に酸を導入し、次に、溶媒除去することによって、容
易に得ることができる。The acid addition salt thereof can be easily obtained, for example, by introducing an acid into the reaction solution after the reaction is completed, and then removing the solvent.
本発明の化合物（Ｉ）（（Ｉ’）及び／又は（Ｉ”）〕
は、農園芸における病原菌（例えば、コムギ赤さび病、
オオムギうどんこ病、キュウリ灰色べと病、イネいもち
病に対し極めて有効であり、その他、トマト疫病などに
有用。）などに顕著な殺菌効果を有する。また、本発明
の化合物（Ｉ）は、農園芸害虫（例えは、ウンカ類、ヨ
コハイ類、アブラムシ類、ヨトウムシ類、コナガ、ミカ
ンハダニ、ナミハダニなど）に有用である。Compound (I) of the present invention ((I') and/or (I''))
are pathogenic bacteria in agriculture and horticulture (e.g. wheat rust,
It is extremely effective against barley powdery mildew, cucumber gray downy mildew, and rice blast, and is also useful against tomato late blight. ) has a remarkable bactericidal effect. Furthermore, the compound (I) of the present invention is useful against agricultural and horticultural pests (eg, planthoppers, leafhoppers, aphids, armyworms, diamondback moths, orange spider mites, two-spotted spider mites, etc.).
本発明の殺菌剤は、化合物（１）の１種以上を有効成分
として含有するものである。The fungicide of the present invention contains one or more compounds (1) as an active ingredient.
化合物（１）は、単独で使用することもできるが、通常
は常法によって、担体、界面活性剤、分散剤、補助剤な
どを配合（例えば、粉剤、乳剤、微粒剤、粒剤、水和剤
、油性の懸濁液、エアゾールなどの組成物として調製す
る）して使用することが好ましい。Compound (1) can be used alone, but it is usually mixed with carriers, surfactants, dispersants, adjuvants, etc. (for example, powders, emulsions, fine granules, granules, hydrated It is preferable to prepare a composition such as a drug, an oily suspension, an aerosol, etc.).
担体としては、例えば、タルク、ベントナイト、クレー
、カオリン、ケイソウ土、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
；炭化水素（ケロシン、鉱油など）、芳香族炭化水素（
ベンゼン、トルエン、キシレンなど）、塩素化炭化水素
（クロロホルム、四塩化炭素など）、エーテル類（ジオ
キサン、テトラヒドロフランなど）、ケトン類（アセト
ン、シクロヘキサノン、イソホロンなど）、エステル類
（酢酸エチル、エチレングリコールアセテート、マレイ
ン酸ジブチルなど）、アルコール類（メタノール、ｎ−
ヘキサノール、エチレングリコールなと）、極性溶媒（
ジメチルホルムアミド、ジメチルスルホキシドなど）、
水などの液体担体；空気、窒素、炭酸ガス、フレオンな
どの気体担体（この場合には、混合噴射することができ
る）などを挙げることがでる。Examples of carriers include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea; hydrocarbons (kerosene, mineral oil, etc.), aromatic hydrocarbons (
benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (ethyl acetate, ethylene glycol acetate, etc.) , dibutyl maleate, etc.), alcohols (methanol, n-
hexanol, ethylene glycol), polar solvents (
dimethylformamide, dimethyl sulfoxide, etc.),
Examples include liquid carriers such as water; gas carriers such as air, nitrogen, carbon dioxide, and freon (in this case, they can be mixed and injected).
末剤の動植物への付着、吸収の向上、薬剤の分散、乳化
、展着などの性能を向上させるために使用できる界面活
性剤や分散剤としては、例えば、アルコール硫酸エステ
ル類、アルキルスルホン酸塩、リグニンスルホン酸塩、
ポリオキシエチレングリコールエーテルなどを挙げるこ
とができる。Examples of surfactants and dispersants that can be used to improve the adhesion and absorption of powders to animals and plants, as well as the dispersion, emulsification, and spreading of drugs, include alcohol sulfate esters and alkyl sulfonates. , lignin sulfonate,
Examples include polyoxyethylene glycol ether.
そして、その製剤の性状を改善するためには、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
、アラビアゴムなどを補助剤として用いることができる
。In order to improve the properties of the preparation, for example,
Carboxymethyl cellulose, polyethylene glycol, gum arabic, etc. can be used as adjuvants.
末剤の製造では、前記の担体、界面活性剤、分散剤及び
補助剤をそれぞれの目的に応じて、各々単独で又は適当
に組み合わせて使用することができる。In producing the powder, the carrier, surfactant, dispersant, and auxiliary agent described above can be used individually or in appropriate combinations depending on the purpose.
本発明の化合物（Ｉ）を製剤化した場合の有効成分濃度
は、乳剤では通常１〜５０重量％、粉剤では通常０．３
〜２５重量％、水和剤では通常１〜９０重量％、粒剤で
は通常０．５〜５重量％、油剤では通常０．５〜５重量
％、エアゾールでは通常０゜１〜５重量％である。When the compound (I) of the present invention is formulated, the concentration of the active ingredient is usually 1 to 50% by weight in an emulsion, and usually 0.3% in a powder.
-25% by weight, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for granules, usually 0.5 to 5% by weight for oils, and usually 0.1 to 5% by weight for aerosols. be.
これらの製剤を適当な濃度に希釈して、それぞれの目的
に応じて、植物茎葉、土壌、水田の水面に散布するか、
又は直接施用することによって各種の用途に供すること
ができる。These preparations can be diluted to an appropriate concentration and sprayed on plant foliage, soil, or the water surface of paddy fields, depending on the purpose.
Alternatively, it can be applied directly for various purposes.
以下、本発明を参考例及び実施例によって示す。 Hereinafter, the present invention will be illustrated by reference examples and examples.
なお、これらの実施例は、本発明の範囲を限定するもの
ではない。Note that these Examples do not limit the scope of the present invention.
参考例１
〔原料化合物（Ｉ［）の台底〕
■〔ｄ−α−メチル−４−ジフルオロメチルチオベンジ
ルアミンの台底〕
水素化リチウムアル≧ニウム（５ｇ、１３０ｍｍｏ ｊ
２）をエーテル（３００ｍｆ）に懸濁し、室温攪拌下、
４−ジフルオロメチルチオアセトフェノンオキシム（１
２ｇ、５５ｍｍｏ １）のエーテル溶液を徐々に滴下し
た。滴下終了後、５時間加熱還流した。Reference Example 1 [Bottom of raw material compound (I[)] ■ [Bottom of d-α-methyl-4-difluoromethylthiobenzylamine] Lithium aluminum hydride (5 g, 130 mmo
2) was suspended in ether (300mf) and stirred at room temperature.
4-difluoromethylthioacetophenone oxime (1
A solution of 2 g, 55 mmol 1) in ether was gradually added dropwise. After the dropwise addition was completed, the mixture was heated under reflux for 5 hours.
反応後、エタノール、次いで、水で過剰の水素化リチウ
ムアルミニウムを分解した。After the reaction, excess lithium aluminum hydride was decomposed with ethanol and then water.
不溶物をセライトで濾去し、濾液を２Ｎ塩酸で抽出した
。この抽出液を２Ｎ水酸化ナトリウムでアルカリ性にし
、酢酸エチルで抽出した。これを無水硫酸ナトリウムで
乾燥後、溶媒を留去した。Insoluble materials were removed by filtration through Celite, and the filtrate was extracted with 2N hydrochloric acid. This extract was made alkaline with 2N sodium hydroxide and extracted with ethyl acetate. After drying this with anhydrous sodium sulfate, the solvent was distilled off.
得られた油状物をカラムクロマトグラフィー（ワコーゲ
ルＣ−２００、エタノール溶出）で精製することによっ
て、原料化合物（ＩＩ［）であるｄ−α−メチル−４−
ジフルオロメチルチオベンジルアミンを６ｇ得た。The obtained oil was purified by column chromatography (Wako Gel C-200, ethanol elution) to obtain d-α-methyl-4- which is the starting compound (II[).
6 g of difluoromethylthiobenzylamine was obtained.
実施例１
■〔ｄ−５−クロロ−６−メチル−４−（α−メチル−
４−ジフルオロメチルチオベンジルアミノ）ピリミジン
（化合物ｌ）の合成〕原料化合物（ｎ）である４、５−
ジクロロ−６−メチルピリミジン（１，０ｇ、６．１ｍ
ｍｏｆ）、原料化合物（Ｉ［）である准−α−メチル−
４−ジフルオロメチルチオベンジルアミン（１，０ｇ、
４゜９ｍｍｏｌ）、及びトリエチルアミン（１ｄ）をト
ルエン（２０ｄすに溶解し、触媒量の４−（Ｎ。Example 1 ■ [d-5-chloro-6-methyl-4-(α-methyl-
Synthesis of 4-difluoromethylthiobenzylamino)pyrimidine (compound l)] 4,5- which is the starting compound (n)
Dichloro-6-methylpyrimidine (1.0g, 6.1m
mof), the starting compound (I[) is the quasi-α-methyl-
4-difluoromethylthiobenzylamine (1,0g,
4°9 mmol) and triethylamine (1d) were dissolved in toluene (20d), and a catalytic amount of 4-(N.
Ｎ−ジメチルア逅〕）ピリジンを添加し、８時間加熱還
流した。Pyridine was added and the mixture was heated under reflux for 8 hours.
反応後、この反応液を水洗し、無水硫酸ナトリウムで乾
燥後、減圧下でトルエンを留去した。After the reaction, the reaction solution was washed with water, dried over anhydrous sodium sulfate, and then toluene was distilled off under reduced pressure.
得られた油状物をシリカゲルカラムクロマトグラフィー
（ワコーゲルＣ−２００、トルエン：酢酸エチル−５＝
１溶出）によって単離し、無色油状物である目的化合物
（第１表中に化合物１として示した。）を０．９ｇ得た
。The obtained oil was subjected to silica gel column chromatography (Wakogel C-200, toluene:ethyl acetate-5=
1 elution) to obtain 0.9 g of the target compound (shown as Compound 1 in Table 1) as a colorless oil.
■（ｄｌ−５−クロロ−６−ニチルー４−（α−メチル
−４−ジフルオロメチルチオベンジルアミノ）ピリミジ
ン（化合物６）の合成〕原料化合物（Ｉｆ）である４、
５−ジクロロー６−エチルピリミジン（２，３ｇ、１３
ｍｍｏ１）、原料化合物（ＩＩＩ）であるｄ−α−メチ
ル−４−ジフルオロメチルチオベンジルアミン（２，３
ｇ、１１ｍｍｏｊ２）、及びトリエチルアミン（２ｄ）
をトルエン（２０ｍ）に溶解し、触媒量の４−（Ｎ。(Synthesis of dl-5-chloro-6-nityl-4-(α-methyl-4-difluoromethylthiobenzylamino)pyrimidine (compound 6)) 4, which is the starting compound (If),
5-dichloro-6-ethylpyrimidine (2.3g, 13
mmo1), d-α-methyl-4-difluoromethylthiobenzylamine (2,3
g, 11 mmoj2), and triethylamine (2d)
was dissolved in toluene (20 m) and a catalytic amount of 4-(N.
Ｎ−ジメチルアミノ）ピリジンを添加し、８時間加熱還
流した。N-dimethylamino)pyridine was added and the mixture was heated under reflux for 8 hours.
反応後、この反応液を水洗し、無水硫酸ナトリウムで乾
燥後、減圧下でトルエンを留去した。After the reaction, the reaction solution was washed with water, dried over anhydrous sodium sulfate, and then toluene was distilled off under reduced pressure.
得られた油状物をシリカゲルカラムクロマトグラフィー
（ワコーゲルＣ−２００，）ルエン：酢酸エチル＝５＝
１溶出）によって単離し、次いで、ｎ−へキサンを用い
て結晶化させることによって、無色の結晶である目的化
合物（第１表中に化合物６として示した。）を２．０ｇ
得た。The obtained oil was subjected to silica gel column chromatography (Wakogel C-200,) luene:ethyl acetate=5=
1 elution) and then crystallized using n-hexane to obtain 2.0 g of the desired compound (shown as Compound 6 in Table 1) as colorless crystals.
Obtained.
■〔ａ−５−クロロ−６−ニチルー４−（α−メチル−
４−ジフルオロメタンスルフィニルベンジルアミノ）ピ
リミジン（化合物７）、及びｄｌ−５−クロロ−６−ニ
チルー４−（α−メチル−４−ジフルオロメタンスルホ
ニルベンジルアノ）ピリミジン（化合物８）の合成］前
記の化合物６（２，６ｇ、７．６ｍｍｏｌ）を塩化メチ
レン（３０ｍｊ２）に溶解し、室温攪拌下、ｍ−クロロ
過安息香酸（２，３ｇ、１０．７ｍｍ。■ [a-5-chloro-6-nityl-4-(α-methyl-
Synthesis of 4-difluoromethanesulfinylbenzylamino)pyrimidine (Compound 7) and dl-5-chloro-6-nityl-4-(α-methyl-4-difluoromethanesulfonylbenzylamino)pyrimidine (Compound 8)] The above-mentioned compound 6 (2.6 g, 7.6 mmol) was dissolved in methylene chloride (30 mj2), and m-chloroperbenzoic acid (2.3 g, 10.7 mm) was dissolved under stirring at room temperature.
ｌ）を加えた。５時間攪拌後、反応液をクロロホルムで
抽出した。この抽出液を２Ｎ水酸化ナトリウム、水で洗
浄後、無水硫酸ナトリウムで乾燥した。そして、溶媒を
減圧下留去し、得られた油状物をシリカゲルカラムクロ
マトグラフィー（ワコーゲルＣ−２００、トルエン：酢
酸エチル−３：ｌ溶出）によって精製した。l) was added. After stirring for 5 hours, the reaction solution was extracted with chloroform. This extract was washed with 2N sodium hydroxide and water, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the obtained oil was purified by silica gel column chromatography (Wakogel C-200, elution with toluene:ethyl acetate-3:l).
無色の結晶である目的化合物（第１表中に化合物８とし
て示した。）を１５０ｍｇ、さらに、無色油状物である
目的化合物（第１表中に化合物７として示した。）を１
．３ｇ得た。150 mg of the target compound as a colorless crystal (shown as Compound 8 in Table 1), and 150 mg of the target compound as a colorless oil (shown as Compound 7 in Table 1).
．． I got 3g.
■〔第１表中の化合物１．１４．１５の台底〕■〜■の
いずれかの合成方法と同様にして、第１表に示したよう
な目的化合物（Ｉ）（第１表中に化合物１．１４．１５
として示した。）を得ることができた。■ [The base of compounds 1.14.15 in Table 1] In the same manner as in any of the synthesis methods of ■ to ■, the target compound (I) as shown in Table 1 ( Compound 1.14.15
It was shown as ) was able to be obtained.
実施例２
■Ｃ粒剤の調製〕
化合物１を５重量部、ベントナイト３５重量部、タルク
５７重量部、ネオペレックスパウダー（商品名；花王ア
トラス製）１重量部及びリグニンスルホン酸ソーダ２重
量部を均一に混合し、次いで少量の水を添加して混練し
た後、造粒、乾燥して粒剤を得た。Example 2 Preparation of C granules] 5 parts by weight of Compound 1, 35 parts by weight of bentonite, 57 parts by weight of talc, 1 part by weight of Neoperex powder (trade name; manufactured by Kao Atlas) and 2 parts by weight of sodium lignin sulfonate. After uniformly mixing and kneading with a small amount of water added, the mixture was granulated and dried to obtain granules.
■〔水和剤の調製〕
化合物１を５０重量部、カオリン４８重量部及びネオペ
レックスパウダー（商品名；花王アトラス製）２重量部
とを均一に混合し、次いで粉砕して水和剤を得た。■ [Preparation of hydrating powder] 50 parts by weight of Compound 1, 48 parts by weight of kaolin and 2 parts by weight of Neoperex powder (trade name; Kao Atlas Co., Ltd.) were mixed uniformly, and then pulverized to obtain a hydrating powder. Ta.
■〔乳剤の調製〕
化合物ｌを２０重量部、キシレン７０重量部及びキシレ
ン７０重量部にトキサノン（商品名；三洋化戒工業製）
１０重量部を加えて均一に混合し、溶解して乳剤を得た
。■ [Preparation of emulsion] Add 20 parts by weight of Compound 1, 70 parts by weight of xylene, and 70 parts by weight of xylene toxanone (trade name; manufactured by Sanyo Kakai Industries).
10 parts by weight were added, mixed uniformly, and dissolved to obtain an emulsion.
■〔粉剤の調製〕
化合物１を５重量部、タルク５０重量部及びカオリン４
５重量部を均一に混合して粉剤を得た。■ [Preparation of powder] 5 parts by weight of compound 1, 50 parts by weight of talc and 4 parts of kaolin
A powder was obtained by uniformly mixing 5 parts by weight.
実施例３
■〔コムギ赤さび病に対する防除効力試験（予防効果）
］
直径６ｃｍのプラスチック植木鉢に１鉢あたり１０本づ
つコムギ（品種：コプシコムギ）を育威し、１．５葉期
の幼植物体に、実施例２に準じて調製した第１表で示し
た目的化合物（１）の水和剤を、界面活性剤（０，０１
％）を含む水で５０ｐｐｍに希釈して、１鉢あたり２０
ｍｊ！で散布した。Example 3 ■ [Control efficacy test against wheat rust (preventive effect)
] Wheat (variety: Kopsi wheat) was grown in plastic flower pots with a diameter of 6 cm, 10 plants per pot, and young plants at the 1.5 leaf stage were prepared according to Example 2 for the purpose shown in Table 1. The hydrating agent of compound (1) was combined with a surfactant (0.01
%) to 50 ppm per pot.
mj! It was sprayed with.
散布後、２日間ガラス温室で栽培し、次いで、コムギ赤
さび病菌（Ｐｕｃｃｉｎｉａ ｄｉｓｐｅｒｓａ）の胞
子懸濁液（７Ｘ１０’胞子／ ｍ ｌ ）を植物体に均
一に噴霧接種した。After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then a spore suspension (7×10′ spores/ml) of Puccinia dispersa was spray-inoculated uniformly onto the plants.
接種後、１週間ガラス温室内で育威し、第−葉に現れた
コムギ赤さび病病斑の程度を調査した。After inoculation, the plants were grown in a glass greenhouse for one week, and the extent of wheat rust lesions that appeared on the first leaves was examined.
薬剤効果の評価は、無処理区の病斑の程度と比較して、
６段階（Ｏ：全体が罹病、１：病斑面積が６０％程度、
２：病斑面積が４０％程度、３：病斑面積が２０％程度
、４：病斑面積が１０％以下、５：病斑無し）で示した
。The drug effect was evaluated by comparing the degree of lesions in the untreated area.
6 stages (O: whole body affected, 1: lesion area approximately 60%,
2: Lesion area is approximately 40%, 3: Lesion area is approximately 20%, 4: Lesion area is 10% or less, 5: No lesion).
なお、対照化合物としては、次に示したような化合物Ａ
（特開昭５９−３６６６６号公報に記載の化合物）又は
化合物Ｂ（特開昭６４−６８３６２号公報記載の化合物
）を使用した。In addition, as a control compound, the following compound A
(compound described in JP-A-59-36666) or compound B (compound described in JP-A-64-68362).
（化合物Ａ）；
第２表
化 合 物 コムキ赤さび病に
対する予防効果
化合物Ａ １
化合物Ｂ１
無処理 Ｏ
（化合物Ｂ）；
（以下、余白）
１０本づつネオムギ（品種：黒ムギ）を育成し、１．５
葉期の幼植物体に、第１表で示した目的化合物（１）か
ら実施例２に準じて調製した水和剤を、界面活性剤（０
，０１％）を含む水で５０ｐｐｍに希釈して、１鉢あた
り２０ｄで散布した。(Compound A); Table 2 Compound Preventive effect against wheat leaf rust Compound A 1 Compound B1 No treatment O (Compound B); .5
A hydrating agent prepared according to Example 2 from the target compound (1) shown in Table 1 was applied to young plants at the leaf stage, and a surfactant (0
, 01%) to 50 ppm and sprayed at 20 d per pot.
散布後、２日間ガラス温室で栽培し、次いで、罹病葉か
ら集めたネオムギうどんこ病１１（Ｅｒｙｓｉｐｈｅｇ
ｒａ＋ｗｉｎｉｓ）の分生胞子を植物体に均一に振り掛
けて接種した。After spraying, it was cultivated in a glass greenhouse for 2 days, and then neowheat powdery mildew 11 (Erysipheg
The plants were inoculated by uniformly sprinkling conidia of ``Ra+winis'' onto the plants.
接種後、１週間ガラス温室内で育威し、第−葉に現れた
ネオムギうどんこ病病斑の程度を調査した。After inoculation, the plants were grown in a glass greenhouse for one week, and the extent of neo-wheat powdery mildew lesions that appeared on the first leaves was examined.
その薬剤効果の判定の結果を、■と同様の評価方法で第
３表に示す。なお、対照化合物としては、■に記載した
化合物Ａ又は化合物Ｂを用いた。The results of the drug effect evaluation are shown in Table 3 using the same evaluation method as in ■. In addition, as a control compound, Compound A or Compound B described in (1) was used.
■〔キュウリベと病に対する防除効力試験（予防効果）
〕
直径６ｃｍのプラスチック植木鉢に１鉢あたり１本づつ
キュウリ（品種；和積半白）を育威し、１．５葉期の幼
植物体に、実施例２に準じて調製した第１表、で示した
目的化合物（１）の水和剤を、界面活性剤（０，０１％
）を含む水で５００ｐｐｍに希釈して、ｌ鉢あたり２０
Ｉｄで散布した。■[Cucumber and disease control efficacy test (preventive effect)
] One cucumber (variety: Wasumi Hanshiro) per pot was grown in a plastic flower pot with a diameter of 6 cm, and the young plants at the 1.5 leaf stage were prepared according to Example 2. A hydrating agent for the target compound (1) shown in is mixed with a surfactant (0.01%
) diluted to 500 ppm with water containing 20
Sprayed with Id.
散布後、２日間ガラス温室で栽培し、次いで、キュウリ
ペと病菌遊走子嚢を罹病葉から調製し、これを植物葉の
裏面にまんべんなく噴霧接種した。After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then cucumbers and zoosporangia of the diseased fungi were prepared from the diseased leaves and evenly sprayed and inoculated onto the undersides of the plant leaves.
接種後、２日間２０℃で暗黒下に保った後、５日間ガラ
ス温室内で育威し、第−葉に現れたキュウリペと病病斑
の程度を調査した。After inoculation, the plants were kept in the dark at 20°C for 2 days and then grown in a glass greenhouse for 5 days, and the extent of cucumbers and lesions that appeared on the first leaves was examined.
その薬剤効果の判定の結果を、■と同様の評価方法で第
４表に示す。The results of the drug effect evaluation are shown in Table 4 using the same evaluation method as in ■.
なお、対照化合物としては、■に記載した化合物Ａ又は
化合物Ｂを用いた。In addition, as a control compound, Compound A or Compound B described in (1) was used.
（以下、余白）
〔発明の効果〕
本発明のフルオロメチルチオ基を有する化合物は、メト
キシ基を有する類似化合物に比べて顕著に改善された殺
菌効果を有する。(Hereinafter, in the margins) [Effects of the Invention] The compound having a fluoromethylthio group of the present invention has a bactericidal effect that is significantly improved compared to a similar compound having a methoxy group.
Claims (3)
子を表し；Ｒ＿３は低級アルキル基を表し；或いは、Ｒ
＿２とＲ＿３とは、それらが結合している炭素原子と共
にピリミジン環に縮合して、硫黄原子１個を有していて
もよい飽和又は不飽和の５もしくは６員環を表し；Ｒ＿
４は水素原子を表し；Ｒ＿５は低級アルキル基又はシク
ロアルキル基を表し；Ｒ＿６は水素原子を表し；ｍは０
、１又は２を表し；ｎは１を表す。） で示されるアラルキルアミン誘導体又はその酸付加塩。(1) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R_1 represents a hydrogen atom; R_2 represents a halogen atom; R_3 represents a lower alkyl group; or R
_2 and R_3 are fused to a pyrimidine ring together with the carbon atom to which they are bonded, and represent a saturated or unsaturated 5- or 6-membered ring which may have one sulfur atom; R_
4 represents a hydrogen atom; R_5 represents a lower alkyl group or a cycloalkyl group; R_6 represents a hydrogen atom; m is 0
, represents 1 or 2; n represents 1. ) Aralkylamine derivatives or acid addition salts thereof.
義であり；Ｘは脱離基を表す。） で示される化合物と 次式： ▲数式、化学式、表等があります▼（III） （式中、Ｒ＿１、Ｒ＿５、Ｒ＿６及びｎは請求項１記載
と同義である。） で示される化合物とを反応させて、 次式： ▲数式、化学式、表等があります▼（ I ′） （式中、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５、Ｒ
＿６及びｎは請求項１記載と同義である。） で示される化合物を得、次にこの化合物（ I ′）を過
酸化物で酸化することによって、 次式： ▲数式、化学式、表等があります▼（ I ″） （式中、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５、Ｒ
＿６及びｎは請求項１記載と同義であり；ｍ′は１又は
２を表す。） で示される化合物を得ることを特徴とする請求項１記載
の式（ I ）で示されるアラルキルアミン誘導体又はそ
の酸付加塩の製造法。(2) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (In the formula, R_2, R_3 and R_4 have the same meanings as described in claim 1; X represents a leaving group.) By reacting a compound with a compound represented by the following formula: ▲Mathematical formula, chemical formula, table, etc.▼(III) (In the formula, R_1, R_5, R_6 and n have the same meanings as described in claim 1.) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I') (In the formula, R_1, R_2, R_3, R_4, R_5, R
_6 and n have the same meanings as in claim 1. ), and then by oxidizing this compound (I ′) with peroxide, the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼( I ″) (In the formula, R_1, R_2 , R_3, R_4, R_5, R
_6 and n have the same meanings as in claim 1; m' represents 1 or 2; ) A method for producing an aralkylamine derivative represented by the formula (I) or an acid addition salt thereof according to claim 1, characterized in that a compound represented by the formula (I) is obtained.
アミン誘導体又はその酸付加塩を有効成分とする殺菌剤
。(3) A disinfectant containing an aralkylamine derivative represented by formula (I) or an acid addition salt thereof according to claim 1 as an active ingredient.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2075662A JPH03275675A (en) | 1990-03-27 | 1990-03-27 | Aralkylamine derivative, production thereof and germicide |
| EP19900311401 EP0424125A3 (en) | 1989-10-18 | 1990-10-17 | Aralkylamine derivatives, preparation method thereof and fungicides containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2075662A JPH03275675A (en) | 1990-03-27 | 1990-03-27 | Aralkylamine derivative, production thereof and germicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03275675A true JPH03275675A (en) | 1991-12-06 |
Family
ID=13582656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2075662A Pending JPH03275675A (en) | 1989-10-18 | 1990-03-27 | Aralkylamine derivative, production thereof and germicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03275675A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013500985A (en) * | 2009-07-30 | 2013-01-10 | メリアル リミテッド | Insecticidal 4-amino-thieno [2,3-d] -pyrimidine compounds and methods of use |
-
1990
- 1990-03-27 JP JP2075662A patent/JPH03275675A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013500985A (en) * | 2009-07-30 | 2013-01-10 | メリアル リミテッド | Insecticidal 4-amino-thieno [2,3-d] -pyrimidine compounds and methods of use |
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