JPH048435B2 - - Google Patents
Info
- Publication number
- JPH048435B2 JPH048435B2 JP15360583A JP15360583A JPH048435B2 JP H048435 B2 JPH048435 B2 JP H048435B2 JP 15360583 A JP15360583 A JP 15360583A JP 15360583 A JP15360583 A JP 15360583A JP H048435 B2 JPH048435 B2 JP H048435B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl group
- lower alkyl
- formula
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 201000010099 disease Diseases 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- -1 acid amide chloride Chemical class 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- LRHFGBDYKMSVMK-UHFFFAOYSA-N 7-nitro-2,3-dihydro-1,4-benzodioxin-6-ol Chemical compound O1CCOC2=C1C=C(O)C([N+]([O-])=O)=C2 LRHFGBDYKMSVMK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 32
- 239000000203 mixture Substances 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000009472 formulation Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000005507 spraying Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 240000008067 Cucumis sativus Species 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 9
- 241000233679 Peronosporaceae Species 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 241000233866 Fungi Species 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 229920003023 plastic Polymers 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 6
- 240000003768 Solanum lycopersicum Species 0.000 description 6
- 235000009754 Vitis X bourquina Nutrition 0.000 description 6
- 235000012333 Vitis X labruscana Nutrition 0.000 description 6
- 240000006365 Vitis vinifera Species 0.000 description 6
- 235000014787 Vitis vinifera Nutrition 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000004927 clay Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000011081 inoculation Methods 0.000 description 5
- 230000000361 pesticidal effect Effects 0.000 description 5
- 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
- 241000233614 Phytophthora Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 241001385948 Pythium sp. Species 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 241000219094 Vitaceae Species 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 244000000005 bacterial plant pathogen Species 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000021021 grapes Nutrition 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000233645 Phytophthora nicotianae Species 0.000 description 2
- 241000233639 Pythium Species 0.000 description 2
- 241000918585 Pythium aphanidermatum Species 0.000 description 2
- 244000300264 Spinacia oleracea Species 0.000 description 2
- 235000009337 Spinacia oleracea Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001580 bacterial effect Effects 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
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000002255 vaccination Methods 0.000 description 2
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical group C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 244000308746 Cucumis metuliferus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 101000635799 Homo sapiens Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Proteins 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000118319 Peronospora effusa Species 0.000 description 1
- 241000233616 Phytophthora capsici Species 0.000 description 1
- 241000233618 Phytophthora cinnamomi Species 0.000 description 1
- 241001505682 Plasmopara nivea Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 1
- 241000599030 Pythium debaryanum Species 0.000 description 1
- 241001505297 Pythium irregulare Species 0.000 description 1
- 241001622896 Pythium myriotylum Species 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 102100030852 Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Human genes 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000005215 alkyl ethers Chemical class 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
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-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
- 238000000034 method Methods 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、一般式〔〕
〔式中、R1は水素原子、低級アルキル基、低
級アルケニル基、低級アルキニル基、ハロ低級ア
ルキル基、チアシクロアルキル基、シアノ低級ア
ルキル基または低級アルコキシ低級アルキル基を
表わし、R2は低級アルキル基または低級アルコ
キシル基を表わす。〕
で示されるチオノリン酸アミド誘導体（以下、本
発明化合物と記す。）、その製造法およびそれを有
効成分とする植物病害防除剤に関するものであ
る。
本発明者らは植物病害防除剤について鋭意検討
を行なつた結果、本発明化合物が多くの植物病原
菌、特にべと病菌や疫病菌等の藻菌類に属する植
物病原菌に対して予防的、治療的あるいは浸透移
行的植物病害防除効力を有することを見出した。
上述の藻菌類に属する植物病原菌には、蔬菜類
やダイコンのべと病菌（Peronospora
brassicae）、ホウレン草のべと病菌
（Peronospora spinaciae）、タバコのべと病菌
（Pseudoperonospora cubensis）、ブドウのべと
病菌（Plasmopara viticola）、セリ科植物のべ
と病菌（Plasmopara nivea）、リンゴ、イチゴ、
ヤクヨウニンジンの疫病菌（Phytophthora
cactorum）、トマト、キユウリの灰色疫病菌
（Phytophthora capsici）、パイナツプルの疫病
菌（Phytophthora cinna−momi）、ジヤガイモ、
トマト、ナスの疫病菌（Phytophthora
infestans）、タバコ、ソラマメ、ネギの疫病菌
（Phytophthora nicotianae var nicotianae）、
キユウリ苗立枯病菌（Pythium
sphanidermatum）、ホウレンソウ立枯病菌
（Pythium sp.）、コムギ褐色雪腐病菌（Pythium
sp.）、タバコ苗立枯病菌（Pythium
debaryanum）、ダイズのPythium Rot（Pythium
aphanidermatum，P.debaryanum，P.
irregulare，P.myriotylum，P.ultimnm）等があ
る。
従つて、本発明化合物は、畑地、果樹園、茶
園、桑園、牧草地、芝生地等の植物病害防除剤の
有効成分として用いることができる。
次に本発明化合物の製造方法について述べる。
本発明化合物は、一般式〔〕
〔式中、R′1は低級アルキル基、低級アルケニ
ル基、低級アルキニル基、ハロ低級アルキル基、
チアシクロアルキル基、シアノ低級アルキル基ま
たは低級アルコキシ低級アルキル基を表わし、
R2は前記と同一の意味を表わす。〕
で示されるチイノリン酸アミドクロリドと式
で示される４，５−エチレンジオキシ−２−ニト
ロフエノールとを溶媒中、脱酸剤を用いて縮合さ
せることによつて製造することができる。
溶媒としては、ベンゼン、トルエン、キシレン
等の芳香族炭化水素、アセトン、メチルイソブチ
ルケトン等のケトン、アセトニトリル、ジメチル
ホルムアミド等が挙げられる。脱酸剤としては、、
炭酸カリウム、水酸化ナトリウム等の無機塩類、
ピリジン、トリエチルアミン、ピコリン等の有機
塩基があげられる。
反応温度および反応時間は、溶媒あるいは脱酸
剤の種類によつて変わりうるが、通常室温から
120℃ぐらいまでであり、１時間ないし数時間で
ある。
また、本発明化合物は一般式〔〕
R1NH2 〔〕
〔式中、R1は水素原子、低級アルキル基、ハ
ロ低級アルキル基、チアシクロアルキル基、シア
ノ低級アルキル基または低級アルコキシ低級アル
キル基を表わす。〕
で示されるアミンと一般式〔〕
〔式中、R2は低級アルキル基または低級アル
コキシル基を表わす。〕
で示されるアミンとを溶媒中、脱酸剤を用いて縮
合させることによつて製造することができる。
溶媒としては、ベンゼン、トルエン、キシレン
等の芳香族炭化水素、ジエチルエーテル、ジイソ
プロピルエーテル等のエーテル、ジクロルメタ
ン、クロロホルム等のハロゲン化炭化水素等が挙
げられる。脱酸剤としては、炭酸カリウム、水酸
化ナトリウム等の無機塩基、ピリジン、トリエチ
ルアミン、Ｎ，Ｎ−ジエチルアニリン等の有機塩
基があげられる。
反応温度および反応時間は、溶媒あるいは、脱
酸剤の種類によつて変わりうるが、通常０℃から
50℃ぐらいまであり、１時間ないし数時間であ
る。
次に本発明化合物の製造例を示す。
製造例 １
４，５−エチレンジオキシ−２−ニトロフエノ
ール1.97ｇ（0.01モル）をアセトニトリル100mg
に溶かし、これに無水炭酸カリウム末1.40ｇ
（0.01モル）と塩化第一銅10mgを加え、40〜50℃
で30分間撹拌した。次いで同温でＯ−メチル Ｎ
−イソプロピル チオノリン酸アミドクロリド
1.88ｇ（0.01モル）を滴下し、さらに３時間加熱
還流した。その後、無機塩類を別し、アセトニ
トリルを留去して残渣をトルエン50mlに溶かし、
これを３％水酸化ナトリウム水溶液、３％塩酸、
次いで水で洗浄し、無水硫酸マグネシウムで乾燥
した。トルエンを留去して得られた残渣をシリカ
ゲルカラムクロマトグラフイーを用いて精製し
て、Ｏ−メチル Ｏ−４，５−エチレンジオキシ
−２−ニトロフエニル Ｎ−イソプロピル ホス
ホロアミドチオエート1.91ｇを得た。収率55％
m.p.98〜95℃
製造例 ２
Ｏ−エチル Ｏ−４，５−エチレンジオキシ−
２−ニトロフエニル チオノリン酸エステルクロ
リド3.40ｇ（0.01モル）をトルエン50mlに溶か
し、０℃に保つて、アリルアミン0.60ｇ（0.0105
モル）とトリエチルアミン1.1ｇ（0.01モル）と
を滴下し、さらに室温で１時間撹拌した。その
後、３％水酸化ナトリウム水溶液、３％塩酸、次
いで水で洗浄し、無水硫酸マグネシウムで乾燥し
た。トルエンを留去しＯ−エチル Ｏ−４，５−
エチレンジオキシ−２−ニトロフエニル
Ｎ−アリル ホスホロアミドチオエート3.42ｇ
を得た。収率95.0％ m.p.56〜59℃
このような製造法によつて製造できる本発明化
合物のいくつかを、第１表に示す。
The present invention is based on the general formula [] [In the formula, R 1 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a halo lower alkyl group, a thiacycloalkyl group, a cyano lower alkyl group, or a lower alkoxy lower alkyl group, and R 2 represents a lower alkyl group. group or lower alkoxyl group. ] The present invention relates to a thionolinic acid amide derivative represented by (hereinafter referred to as the compound of the present invention), a method for producing the same, and a plant disease control agent containing the same as an active ingredient. The present inventors have conducted intensive studies on plant disease control agents, and have found that the compounds of the present invention have preventive and therapeutic effects against many plant pathogenic bacteria, particularly against plant pathogenic bacteria belonging to the algal fungi such as downy mildew and Phytophthora. It has also been found that it has systemic plant disease control efficacy. Plant pathogenic bacteria belonging to the above-mentioned algae and fungi include Peronospora mildew on vegetables and radish.
brassicae), downy mildew of spinach (Peronospora spinaciae), downy mildew of tobacco (Pseudoperonospora cubensis), downy mildew of grapes (Plasmopara viticola), downy mildew of umbelliferous plants (Plasmopara nivea), apple, strawberry,
Phytophthora Phytophthora
Phytophthora capsici on tomatoes, cucumbers, Phytophthora cinna-momi on pineapple, potatoes,
Phytophthora phytophthora of tomatoes and eggplants
Phytophthora nicotianae var nicotianae), Phytophthora nicotianae var nicotianae,
Pythium seedling blight disease fungus
sphanidermatum), spinach damping-off fungus (Pythium sp.), wheat brown snow rot fungus (Pythium sp.
sp.), Pythium sp.
debaryanum), soybean Pythium Rot (Pythium
aphanidermatum, P. debaryanum, P.
irregulare, P. myriotylum, P. ultimnm), etc. Therefore, the compound of the present invention can be used as an active ingredient in a plant disease control agent for fields, orchards, tea gardens, mulberry gardens, pastures, lawns, and the like. Next, a method for producing the compound of the present invention will be described. The compound of the present invention has the general formula [] [In the formula, R′ 1 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a halo-lower alkyl group,
represents a thiacycloalkyl group, a cyano lower alkyl group or a lower alkoxy lower alkyl group,
R 2 has the same meaning as above. ] Thiinophosphoric acid amide chloride and the formula It can be produced by condensing 4,5-ethylenedioxy-2-nitrophenol shown in a solvent using a deoxidizing agent. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene, ketones such as acetone and methyl isobutyl ketone, acetonitrile, and dimethylformamide. As a deoxidizing agent,
Inorganic salts such as potassium carbonate and sodium hydroxide,
Examples include organic bases such as pyridine, triethylamine, and picoline. The reaction temperature and reaction time may vary depending on the type of solvent or deoxidizing agent, but are usually between room temperature and
The temperature is up to about 120℃, and it takes from one hour to several hours. Furthermore, the compound of the present invention has the general formula [] R 1 NH 2 [] [wherein R 1 is a hydrogen atom, a lower alkyl group, a halo-lower alkyl group, a thiacycloalkyl group, a cyano-lower alkyl group, or a lower alkoxy-lower alkyl group] represents. ] Amine shown by the general formula [ ] [In the formula, R 2 represents a lower alkyl group or a lower alkoxyl group. ] It can be produced by condensing the amine shown below in a solvent using a deoxidizing agent. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene, ethers such as diethyl ether and diisopropyl ether, and halogenated hydrocarbons such as dichloromethane and chloroform. Examples of deoxidizing agents include inorganic bases such as potassium carbonate and sodium hydroxide, and organic bases such as pyridine, triethylamine, and N,N-diethylaniline. The reaction temperature and reaction time may vary depending on the type of solvent or deoxidizing agent, but are usually between 0°C and
The temperature is up to about 50℃, and it lasts for one to several hours. Next, production examples of the compounds of the present invention will be shown. Production example 1 1.97 g (0.01 mol) of 4,5-ethylenedioxy-2-nitrophenol was added to 100 mg of acetonitrile.
Dissolve in this and add 1.40 g of anhydrous potassium carbonate powder to this.
(0.01 mol) and 10 mg of cuprous chloride at 40-50℃.
The mixture was stirred for 30 minutes. Then, at the same temperature, O-methyl N
-Isopropyl thionolamide chloride
1.88 g (0.01 mol) was added dropwise, and the mixture was further heated under reflux for 3 hours. Then, the inorganic salts were separated, the acetonitrile was distilled off, and the residue was dissolved in 50 ml of toluene.
This was mixed with 3% sodium hydroxide aqueous solution, 3% hydrochloric acid,
It was then washed with water and dried over anhydrous magnesium sulfate. The residue obtained by distilling off toluene was purified using silica gel column chromatography to obtain 1.91 g of O-methyl O-4,5-ethylenedioxy-2-nitrophenyl N-isopropyl phosphoramidothioate. Obtained. Yield 55%
mp98～95℃ Production example 2 O-ethyl O-4,5-ethylenedioxy-
Dissolve 3.40 g (0.01 mol) of 2-nitrophenyl thionophosphate chloride in 50 ml of toluene, keep at 0°C, and dissolve 0.60 g (0.0105 mol) of allylamine.
mol) and 1.1 g (0.01 mol) of triethylamine were added dropwise, and the mixture was further stirred at room temperature for 1 hour. Thereafter, it was washed with a 3% aqueous sodium hydroxide solution, 3% hydrochloric acid, and then with water, and dried over anhydrous magnesium sulfate. Toluene was distilled off and O-ethyl O-4,5-
Ethylenedioxy-2-nitrophenyl N-allyl phosphoramidothioate 3.42g
I got it. Yield 95.0% mp56-59°C Some of the compounds of the present invention that can be produced by such a production method are shown in Table 1.
【表】【table】
【表】
本発明化合物を植物病害防除剤の有効成分とし
て用いる場合は、他の何らの成分も加えずそのま
までもよいが、通常は、固体担体、液体担体、界
面活性剤その他の製剤用補助剤と混合して、乳
剤、水和剤、懸濁剤、粒剤、粉剤等に製剤する。
これらの製剤には有効成分として本発明化合物
を、重量比で0.1〜99.9％、好ましくは１〜99％
含有する。
固体担体には、カオリンクレー、アツタパルジ
ヤイトクレー、ベントナイト、酸性白土、パイロ
フエライト、タルク、珪藻土、方解石、トウモロ
コシ穂軸粉、クルミ穀粉、尿素、硫酸アンモニウ
ム、合成含水酸化珪素等の微粉末あるいは粒状物
があり、液体担体には、キシレン、メチルフナタ
レン等の芳香族炭化水素、イソプロパノール、エ
チレングリコール、セロソルブ等のアルコール、
アセトン、シクロヘキサノン、イソホロン等のケ
トン、大豆油、綿実油等の植物油、ジメチルスル
ホキシド、アセトニトリル、水等がある。
乳化、分散、湿展等のために用いられる界面活
性剤には、アルキル硫酸エステル塩、アルキル
（アリール）スルホン酸塩、ジアルキルスルホこ
はく酸塩、ポリオキシエチレンアルキルアリール
エーテルりん酸エステル塩、ナフタレンスルホン
酸ホルマリン縮合物等の陰イオン界面活性剤、ポ
リオキシエチレンアルキルエーテル、ポリオキシ
エチレンポリオキシプロピレンブロツクコポリマ
ー、ソルビタン脂肪酸エステル、ポリオキシエチ
レンソルビタン脂肪酸エステル等の非イオン界面
活性剤等がある。製剤用補助剤には、リグニンス
ルホン酸塩、アルギン酸塩、ポリビニルアルコー
ル、アラビアガム、CMC（カルボキシメチルセル
ロース）、PAP（酸性りん酸イソプロピル）等が
ある。
次に製剤例を示す。なお、本発明化合物は第１
表の化合物番号で示す。部は重量部である。
製剤例 １
本発明化合物(2)50部、リグニンスルホン酸カル
シウム３部、ラウリル硫酸ナトリウム２部および
合成含水酸化珪素45部をよく粉砕混合して水和剤
を得る。
製剤例 ２
本発明化合物(1)10部、ポリオキシエチレンスチ
リルフエニルエーテル14部、ドデシルベンゼンス
ルホン酸カルシウム６部、キシレン70部をよく混
合して乳剤を得る。
製剤例 ３
本発明化合物(12)２部、合成含水酸化珪素１部、
リグニンスルホン酸カルシウム２部、ベントナイ
ト30部およびカオリンクレー65部をよく粉砕混合
し、水を加えてよく練り合せた後、造粒乾燥して
粒剤を得る。
製剤例 ４
本発明化合物（17）25部、ポリオキシエチレン
ソルビタンモノオレエート３部、CMC3部、水69
部を混合し、有効成分の粒度が５ミクロン以下に
なるまで湿式粉砕して懸濁剤を得る。
製剤例 ５
本発明化合物（23）２部、カオリンクレー38部
およびタルク10部をよく粉砕混合して粉剤を得
る。
これらの製剤はそのままあるいは水等で希釈
し、茎葉処理あるいは土壌処理する。土壌処理の
場合は製剤を土壌表面に散布する（必要に応じ、
散布後土壌と混和する。）かまたは土壌に潅注す
る。また、他の植物病害防除剤と混合して用いる
ことにより、防除効力の増強を期待できる。さら
に、殺菌剤、土壌害虫防除剤、殺線虫剤、植物生
長調節剤、肥料、土壌改良剤等と混合して用いる
こともできる。
本発明化合物を植物病害防除剤の有効成分とし
て用いる場合、その施用量は通常１アールあたり
0.05ｇ〜100ｇ、好ましくは0.1〜20ｇであり、粒
剤、粉剤、微粒剤等はなんら希釈することなくそ
のまま施用し、乳剤、水和剤、懸濁剤、水溶剤等
を水で希釈して施用する場合、その施用濃度は
0.0005％〜１％、好ましくは0.001％〜0.2％であ
る。
次に、本発明化合物が植物病害防除剤の有効成
分として有用であることを試験例で示す。なお、
本発明化合物は第１表の化合物番号で示し、比較
的対照に用いた化合物は第２表の化合物記号で示
す。[Table] When the compound of the present invention is used as an active ingredient in a plant disease control agent, it may be used as is without adding any other ingredients, but it is usually used in combination with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries. It is mixed with and formulated into emulsions, wettable powders, suspensions, granules, powders, etc. These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 99.9%, preferably 1 to 99%.
contains. Solid carriers include fine powders or granules such as kaolin clay, attapalgite clay, bentonite, acid clay, pyroferrite, talc, diatomaceous earth, calcite, corn cob flour, walnut flour, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Liquid carriers include aromatic hydrocarbons such as xylene and methylfunatarene, alcohols such as isopropanol, ethylene glycol, and cellosolve.
Examples include ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile, and water. Surfactants used for emulsification, dispersion, wetting, etc. include alkyl sulfate ester salts, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, and naphthalene sulfone. Examples include anionic surfactants such as acid formalin condensates, nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters. Formulation adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), and PAP (isopropyl acid phosphate). Examples of formulations are shown below. In addition, the compound of the present invention is the first
Indicated by compound number in the table. Parts are parts by weight. Formulation Example 1 50 parts of the compound of the present invention (2), 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder. Formulation Example 2 10 parts of the compound of the present invention (1), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 70 parts of xylene are thoroughly mixed to obtain an emulsion. Formulation Example 3 2 parts of the compound of the present invention (12), 1 part of synthetic hydrous silicon oxide,
2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, followed by granulation and drying to obtain granules. Formulation Example 4 25 parts of the compound of the present invention (17), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC, 69 parts of water
A suspension is obtained by mixing the two parts and wet-milling until the particle size of the active ingredient is less than 5 microns. Formulation Example 5 2 parts of the compound (23) of the present invention, 38 parts of kaolin clay and 10 parts of talc are thoroughly ground and mixed to obtain a powder. These preparations can be used as they are or diluted with water, etc., and treated with foliage or soil. For soil treatment, spray the preparation on the soil surface (if necessary,
Mix with soil after spraying. ) or irrigate the soil. Furthermore, by mixing and using it with other plant disease control agents, it can be expected that the control effect will be enhanced. Furthermore, it can be used in combination with fungicides, soil pest control agents, nematicides, plant growth regulators, fertilizers, soil conditioners, and the like. When the compound of the present invention is used as an active ingredient of a plant disease control agent, the application amount is usually per 1 are.
The amount is 0.05g to 100g, preferably 0.1 to 20g. Granules, powders, fine granules, etc. are applied as they are without any dilution, and emulsions, wettable powders, suspensions, aqueous solvents, etc. are diluted with water. If applied, the application concentration is
It is 0.0005% to 1%, preferably 0.001% to 0.2%. Next, test examples demonstrate that the compound of the present invention is useful as an active ingredient of a plant disease control agent. In addition,
Compounds of the present invention are indicated by compound numbers in Table 1, and compounds used as comparative controls are indicated by compound symbols in Table 2.
【表】【table】
【表】
また防除効力は、調査時の供試植物の発病状態
すなわち葉、茎等の菌叢、病斑の程度を肉眼観察
し、菌叢、病斑が全く認められなければ「５」、
10％程度認められれば「４」、30％程度認められ
れば「３」、50％程度認められれば「２」、70％程
度認められれば「１」、それ以上で化合物を供試
していない場合の発病状態と差が認められなけれ
ば「０」として、０〜５の６段階に評価し、０，
１，２，３，４，５で示す。
試験例 １
キユウリベと病防除試験（予防効果）
プラスチツクポツトに砂壌土を詰め、キユウリ
（相模半白）を播種し、温室内で14日間育成した。
子葉が展開したキユウリの幼苗に、製剤例２に準
じて乳剤にした供試化合物を水で希釈して所定濃
度にし茎葉散布した。散布後キユウリベと病菌の
胞子懸濁液を噴霧接種した。接種後20℃、多湿下
で１日間、さらに温室内で５日間育成し、防除効
力を調査した。その結果を第３表に示す。[Table] In addition, the control efficacy is determined by visually observing the disease state of the test plants at the time of the survey, that is, the degree of bacterial flora and lesions on leaves, stems, etc., and if no bacterial flora or lesions are observed, it is rated "5".
If about 10% is observed, it is "4", if about 30% is observed, it is "3", if about 50% is observed, it is "2", if about 70% is observed, it is "1", and if the compound is not tested if it is more than that. If there is no difference from the disease onset state, it is evaluated as "0" and evaluated on a scale of 0 to 5.
Shown as 1, 2, 3, 4, 5. Test Example 1 Kyuribe and disease control test (preventive effect) A plastic pot was filled with sandy loam, sown with cucumber (Sagami Hanshiro), and grown in a greenhouse for 14 days.
A test compound prepared as an emulsion according to Formulation Example 2 was diluted with water to a predetermined concentration and sprayed on the foliage of cucumber seedlings with developed cotyledons. After the spraying, a spore suspension of P. cucumber and the disease fungus was inoculated by spraying. After inoculation, the seeds were grown for 1 day at 20°C under high humidity and then for 5 days in a greenhouse, and their pesticidal efficacy was investigated. The results are shown in Table 3.
【表】【table】
【表】
試験例 ２
キユウリベと病防除試験（治療効果）
プラスチツクポツトに砂壌土を詰め、キユウリ
（相模半白）を播種し、温室内で14日間育成した。
子葉が展開したキユウリの幼苗にキユウリベと病
菌の胞子懸濁液を噴霧接種した。接種後20℃、多
湿下で１日間育成し、製剤例２に準じて乳剤にし
た供試化合物を水で希釈して所定濃度にし、それ
を葉面に充分付着するように茎葉散布した。散布
後20℃温室内で５日間育成し、防除効力を調査し
た。その結果を第４表に示す。[Table] Test Example 2 Kiyu cucumber and disease control test (therapeutic effect) A plastic pot was filled with sandy loam, and Ki cucumber (Sagami Hanshiro) was sown and grown in a greenhouse for 14 days.
Young cucumber seedlings with expanded cotyledons were inoculated by spraying with a spore suspension of cucurbita and the disease fungus. After inoculation, the plants were grown for 1 day at 20° C. under humid conditions, and the test compound was made into an emulsion according to Formulation Example 2, diluted with water to a predetermined concentration, and sprayed on the foliage so as to sufficiently adhere to the leaf surface. After spraying, the seeds were grown in a greenhouse at 20°C for 5 days, and their pesticidal efficacy was investigated. The results are shown in Table 4.
【表】【table】
【表】
試験例 ３
キユウリベと病防除試験（浸透移行効果）
プラスチツクポツトに砂壌土を詰め、キユウリ
（相模半白）を播種し、温室内で８日間育成し、
子葉が展開したキユウリの幼苗を得た。製剤例２
に準じて乳剤にした供試化合物を水で希釈し、そ
の所定量を土壌に潅注した。潅注後６日間温室内
で育成し、キユウリベと病菌の胞子懸濁液を噴霧
接種した。接種後20℃、多湿下で１日間、さらに
温室内で５日間育成し、防除効力を調査した。そ
の結果を第５表に示す。[Table] Test example 3. Disease control test with cucumber (penetration transfer effect) A plastic pot was filled with sandy loam, and cucumber (Sagami Hanshiro) was sown and grown in a greenhouse for 8 days.
Young cucumber seedlings with expanded cotyledons were obtained. Formulation example 2
The test compound made into an emulsion according to the method was diluted with water, and a predetermined amount of it was sprinkled onto the soil. After irrigation, the plants were grown in a greenhouse for 6 days and inoculated by spraying with a spore suspension of Cucumber and the disease fungus. After inoculation, the seeds were grown for 1 day at 20°C under high humidity and then for 5 days in a greenhouse, and their pesticidal efficacy was investigated. The results are shown in Table 5.
【表】
試験例 ４
ブドウべと病防除試験（予防効果）
プラスチツクポツトに砂壌土を詰め、ブドウ
（ネオマスの種子）を播種し、温室内で50日間育
成した。第４〜５葉が展開したブドウの幼苗に、
製剤例２に準じて乳剤にした供試化合物を水で希
釈して所定濃度にし茎葉散布した。散布後ブドウ
べと病菌の胞子懸濁液を噴霧接種した。接種後23
℃、多湿下で３日間、さらに温室内で10日間育成
し、防除効力を調査した。その結果を第６表に示
す。[Table] Test Example 4 Grape Downy Mildew Control Test (Preventive Effect) Plastic pots were filled with sandy loam, grapes (neomas seeds) were sown, and grown in a greenhouse for 50 days. Young grape seedlings with 4th and 5th leaves developed,
A test compound made into an emulsion according to Formulation Example 2 was diluted with water to a predetermined concentration and sprayed on foliage. After spraying, a spore suspension of grape downy mildew was inoculated by spraying. 23 days after vaccination
The plants were grown for 3 days at ℃ and high humidity, and then for 10 days in a greenhouse, and their pesticidal efficacy was investigated. The results are shown in Table 6.
【表】
試験例 ５
ブドウべと病防除試験（治療効果）
プラスチツクポツトに砂壌土を詰め、ブドウ
（ネオマスカツトの種）を播種し、温室内で50日
間育成した。第４〜５本葉が展開したブドウの幼
苗にブドウべと病菌の胞子懸濁液を噴霧接種し
た。接種後25℃、多湿下で１日間育成し、製剤例
２に準じて乳剤にした供試化合物を水で希釈して
所定濃度にし、それを葉面に充分付着するように
茎葉散布した。散布後23℃温室内で10日間育成
し、防除効力を調査した。その結果を第７表に示
す。[Table] Test Example 5 Grape Downy Mildew Control Test (Treatment Effect) Plastic pots were filled with sandy loam, grapes (neomuscatus seeds) were sown, and grown in a greenhouse for 50 days. A spore suspension of grape downy mildew was inoculated by spraying onto young grape seedlings in which the 4th to 5th true leaves had developed. After inoculation, the plants were grown for 1 day at 25° C. under humid conditions, and the test compound was made into an emulsion according to Formulation Example 2, diluted with water to a predetermined concentration, and sprayed on the foliage to ensure sufficient adhesion to the leaf surface. After spraying, the plants were grown in a greenhouse at 23°C for 10 days, and their control efficacy was investigated. The results are shown in Table 7.
【表】
試験例 ６
トマト疫病防除試験（治療効果）
プラスチツクポツトに砂壌土を詰め、トマト
（ポンテローザ）を播種し、温室内で20日間育成
した。第３本葉が展開したトマトの幼苗にトマト
疫病菌の胞子懸濁液を噴霧接種した。接種後15
℃、多湿下で１日間育成し、製剤例２に準じて乳
剤にした供試化合物を、水で希釈して所定濃度に
し、それを葉面に充分付着するように茎葉散布し
た。散布後15℃多湿下で６日間育成し、防除効力
を調査した。その結果を第８表に示す。[Table] Test Example 6 Tomato late blight control test (therapeutic effect) Plastic pots were filled with sandy loam, tomatoes (Ponterosa) were sown, and grown in a greenhouse for 20 days. Tomato seedlings that had developed their third true leaves were spray inoculated with a spore suspension of Phytophthora tomato. 15 days after vaccination
The test compound was grown for 1 day at 100° C. under high humidity and made into an emulsion according to Formulation Example 2. The test compound was diluted with water to a predetermined concentration and sprayed on the leaves so as to sufficiently adhere to the leaf surface. After spraying, the plants were grown for 6 days at 15°C and humid, and the control efficacy was investigated. The results are shown in Table 8.
【表】【table】
【表】
試験例 ７
ジヤガイモの疫病防除試験（治療効果）
プラスチツクポツトに砂壌土を詰め、ジヤガイ
モ（男爵）を播種し、温室内で60日間育成した。
この苗にジヤガイモ疫病菌の胞子懸濁液を噴霧接
種した。接種後20℃、多湿下で１日育成し、製剤
例２に準じて乳剤にした供試化合物を水で希釈し
て所定濃度にし、それを葉面に充分付着するよう
に茎葉散布した。散布後20℃多湿下で６日間育成
し、防除効力を調査した。その結果を第９表に示
す。[Table] Test Example 7 Potato blight control test (therapeutic effect) A plastic pot was filled with sandy loam, and potatoes (Baron) were sown and grown in a greenhouse for 60 days.
The seedlings were inoculated by spraying with a spore suspension of Phytophthora blight. After inoculation, the plants were grown for one day at 20°C under high humidity, and the test compound was made into an emulsion according to Formulation Example 2, diluted with water to a predetermined concentration, and sprayed on the foliage so that it would sufficiently adhere to the leaf surface. After spraying, the plants were grown for 6 days at 20°C and humid, and their pesticidal efficacy was investigated. The results are shown in Table 9.
Claims (1)
級アルケニル基、低級アルキニル基、ハロ低級ア
ルキル基、チアシクロアルキル基、シアノ低級ア
ルキル基または低級アルコキシ低級アルキル基を
表わし、R2は低級アルキル基または低級アルコ
キシル基を表わす。〕 で示されるチオノリン酸アミド誘導体。 ２ 一般式 〔式中、R′1は低級アルキル基、低級アルケニ
ル基、低級アルキニル基、ハロ低級アルキル基、
チアシクロアルキル基、シアノ低級アルキル基ま
たは低級アルコキシ低級アルキル基を表わし、
R2は低級アルキル基または低級アルコキシル基
を表わす。〕 で示されるチオノリン酸アミドクロリドと式 で示される４，５−エチレンジオキシ−２−ニト
ロフエノールとを縮合させることを特徴とする一
般式 〔式中、R′1およびR2は前記と同一の意味を表
わす。〕 で示されるチオノリン酸アミド誘導体の製造法。 ３ 一般式 R1NH2 〔式中、R1は水素原子、低級アルキル基、低
級アルケニル基、低級アルキニル基、ハロ低級ア
ルキル基、チアシクロアルキル基、シアノ低級ア
ルキル基または低級アルコキシ低級アルキル基を
表わす。〕 で示されるアミンと一般式 〔式中、R2は低級アルキル基または低級アル
コキシ基を表わす。〕 で示されるチオノリン酸エステルクロリドとを縮
合させることを特徴とする一般式 〔式中、R1およびR2は前記と同一の意味を表
わす。〕 で示されるチオノリン酸アミド誘導体の製造法。 ４ 一般式 〔式中、R1は水素原子、低級アルキル基、低
級アルケニル基、低級アルキニル基、ハロ低級ア
ルキル基、チアシクロアルキル基、シアノ低級ア
ルキル基または低級アルコキシ低級アルキル基を
表わし、R2は低級アルキル基または低級アルコ
キシル基を表わす。〕 で示されるチオノリン酸アミド誘導体を有効成分
として含有することを特徴とする植物病害防除
剤。[Claims] 1. General formula [In the formula, R 1 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a halo lower alkyl group, a thiacycloalkyl group, a cyano lower alkyl group, or a lower alkoxy lower alkyl group, and R 2 represents a lower alkyl group. group or lower alkoxyl group. ] A thionolinamide derivative represented by 2 General formula [In the formula, R′ 1 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a halo-lower alkyl group,
represents a thiacycloalkyl group, a cyano lower alkyl group or a lower alkoxy lower alkyl group,
R 2 represents a lower alkyl group or a lower alkoxyl group. ] Thionolinic acid amide chloride and the formula A general formula characterized by condensing with 4,5-ethylenedioxy-2-nitrophenol represented by [In the formula, R′ 1 and R 2 represent the same meanings as above. ] A method for producing a thionolinamide derivative represented by. 3 General formula R 1 NH 2 [In the formula, R 1 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a halo-lower alkyl group, a thiacycloalkyl group, a cyano-lower alkyl group, or a lower alkoxy-lower alkyl group. represent ] Amine and general formula shown by [In the formula, R 2 represents a lower alkyl group or a lower alkoxy group. ] A general formula characterized by condensation with thionophosphate chloride represented by [In the formula, R 1 and R 2 represent the same meanings as above. ] A method for producing a thionolinamide derivative represented by. 4 General formula [In the formula, R 1 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a halo lower alkyl group, a thiacycloalkyl group, a cyano lower alkyl group, or a lower alkoxy lower alkyl group, and R 2 represents a lower alkyl group. group or lower alkoxyl group. ] A plant disease control agent characterized by containing a thionolinic acid amide derivative represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15360583A JPS6045586A (en) | 1983-08-22 | 1983-08-22 | Thionophosphoric acid amide derivative, its preparation and plant blight controlling agent containing said derivative as active component |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15360583A JPS6045586A (en) | 1983-08-22 | 1983-08-22 | Thionophosphoric acid amide derivative, its preparation and plant blight controlling agent containing said derivative as active component |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6045586A JPS6045586A (en) | 1985-03-12 |
| JPH048435B2 true JPH048435B2 (en) | 1992-02-17 |
Family
ID=15566134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15360583A Granted JPS6045586A (en) | 1983-08-22 | 1983-08-22 | Thionophosphoric acid amide derivative, its preparation and plant blight controlling agent containing said derivative as active component |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6045586A (en) |
-
1983
- 1983-08-22 JP JP15360583A patent/JPS6045586A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6045586A (en) | 1985-03-12 |
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