JPS6239573A - Cycloalkenylamide derivative, production thereof and soil blight controlling agent containing said derivative as active constituent - Google Patents
Cycloalkenylamide derivative, production thereof and soil blight controlling agent containing said derivative as active constituentInfo
- Publication number
- JPS6239573A JPS6239573A JP60177977A JP17797785A JPS6239573A JP S6239573 A JPS6239573 A JP S6239573A JP 60177977 A JP60177977 A JP 60177977A JP 17797785 A JP17797785 A JP 17797785A JP S6239573 A JPS6239573 A JP S6239573A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- derivative
- soil
- cyclohexenyl
- 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
- 239000002689 soil Substances 0.000 title claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000000470 constituent Substances 0.000 title 1
- -1 cycloalkenyl isocyanate Chemical class 0.000 claims abstract description 21
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims abstract description 5
- 239000012948 isocyanate Substances 0.000 claims abstract description 3
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims abstract 4
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims abstract 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims abstract 2
- 201000010099 disease Diseases 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 abstract description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- 150000003512 tertiary amines Chemical class 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002460 imidazoles Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 20
- 241000233866 Fungi Species 0.000 description 19
- 238000009472 formulation Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000008187 granular material Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 6
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 230000000361 pesticidal effect Effects 0.000 description 6
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 5
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 5
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 241000223218 Fusarium Species 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 241000918585 Pythium aphanidermatum Species 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 244000061458 Solanum melongena Species 0.000 description 4
- 235000002597 Solanum melongena Nutrition 0.000 description 4
- 230000001717 pathogenic effect Effects 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 241000220259 Raphanus Species 0.000 description 3
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 3
- 241001361634 Rhizoctonia Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000959260 Typhula Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000013312 flour 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
- 239000007788 liquid Substances 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 241000233639 Pythium Species 0.000 description 2
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 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
- JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 description 2
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 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
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 244000000003 plant pathogen Species 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- AWFYPPSBLUWMFQ-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=C2 AWFYPPSBLUWMFQ-UHFFFAOYSA-N 0.000 description 1
- SULQOTGFPPFUMG-UHFFFAOYSA-N 2-bromo-4,5-dichloro-1h-imidazole Chemical compound ClC=1N=C(Br)NC=1Cl SULQOTGFPPFUMG-UHFFFAOYSA-N 0.000 description 1
- AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 1
- OCKJFOHZLXIAAT-UHFFFAOYSA-N 2-methylsulfanyl-1h-benzimidazole Chemical compound C1=CC=C2NC(SC)=NC2=C1 OCKJFOHZLXIAAT-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical group N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- JXCFZLPMGFBTNY-UHFFFAOYSA-N 3-isocyanatocyclohexene Chemical compound O=C=NC1CCCC=C1 JXCFZLPMGFBTNY-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
- 241001530056 Athelia rolfsii Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000034656 Contusions Diseases 0.000 description 1
- 241000051573 Corticium sp. (in: Fungi) Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000035240 Disease Resistance Diseases 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 241000221779 Fusarium sambucinum Species 0.000 description 1
- 241000233732 Fusarium verticillioides Species 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
- 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
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000599030 Pythium debaryanum Species 0.000 description 1
- 244000155437 Raphanus sativus var. niger Species 0.000 description 1
- 240000001970 Raphanus sativus var. sativus Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000004274 Sarcandra glabra Species 0.000 description 1
- 235000010842 Sarcandra glabra Nutrition 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum 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
- 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
- 241000981595 Zoysia japonica Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004414 alkyl thio 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
- 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
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 208000034526 bruise Diseases 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
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- LFHISGNCFUNFFM-UHFFFAOYSA-N chloropicrin Chemical compound [O-][N+](=O)C(Cl)(Cl)Cl LFHISGNCFUNFFM-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 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
- 239000013078 crystal Substances 0.000 description 1
- 229940117389 dichlorobenzene 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
- 239000003480 eluent Substances 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
- 239000010419 fine particle Substances 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-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
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
本発明は、一般式
〔式中、又はハロゲン原子、低級アルキル基、ニトロ基
、低級アルキルチオ基よりなる置換基で置換されていて
もよいイ主ダシールー１−イル基、ベンズイ定ダシール
ー１−イル基、ベンゾトリアゾール−１−イル基、ピラ
ゾール−１−イル基、１，２．４−）リアゾール−１−
イル基またはインダゾール−１−イル基を表わし、ｎは
１から８までの整数を表わす。〕で示されるシクロアル
ケニルアミド誘導体（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土壌病害防除剤
に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a Dacyl-1-yl group optionally substituted with a substituent consisting of a halogen atom, a lower alkyl group, a nitro group, or a lower alkylthio group, benzyl-1-yl group, benzotriazol-1-yl group, pyrazol-1-yl group, 1,2.4-)riazole-1-yl group
yl group or indazol-1-yl group, and n represents an integer from 1 to 8. ] Cycloalkenylamide derivative (hereinafter referred to as the compound of the present invention),
The present invention relates to a method for producing the same and a soil disease control agent containing the same as an active ingredient.
ある種の２−シクロアルケニルアミン誘導体が土壌病害
防除剤の有効成分として用いられ得 −ることは
特開昭５９−２２２４０８号公報等に記載されている。It is described in JP-A-59-222408, etc. that certain 2-cycloalkenylamine derivatives can be used as active ingredients of soil disease control agents.
しかしながら、従来のこの種の土壌病害防除剤は土壌中
において通常長期の残効性を必要としており、この点で
まだまだ問題が残されている。However, conventional soil disease control agents of this type generally require long-term residual effectiveness in the soil, and problems still remain in this respect.
本発明者らは、高活性でありかつ長期残効性を有する土
壌病害防除剤を検討した結果、後記試験例で示されると
おり本発明化合物が高い活性と公知化合物に優る残効性
を見出し、本発明に至った。As a result of examining soil disease control agents that are highly active and have long-term residual effects, the present inventors found that the compounds of the present invention have high activity and a residual effect superior to known compounds, as shown in the test examples below. This led to the present invention.
本発明化合物は、植物病原菌による土壊病害に対してす
ぐれた防除効果を有する。これらの植物病原菌としては
、フザリウム属のトマト萎ちょう病菌（Ｆｕｓａｒｉｕ
ｍ ｏｘｙｓｐｏｒｕｍ ｆ、 ｓｐ、 Ｉｉ −ｃｏ
ｐｅｒｓｉｃｉ ）、ダイコン要員病菌（Ｆｕｓａｒｉ
ｕｍｏｘｙｓｐｏｒｕｒｎ ｆ、 ｓｐ、 ｒａｐｈａ
ｎｉ）、キュウリ蔓割病閲（Ｆｕｓａｒｉｕｍ ｏｘｙ
ｓｐｒｕｍ ｆ、 ｓｐ、 ｃｕｃｕｍｅｒｉｎｕｍ）
スイカ蔓割病菌（Ｆｕｓａｒｉｕｍ ｏｘｙｓｐｏｒｕ
ｍ ｆ、 ｓｐ。The compounds of the present invention have excellent control effects against soil damage caused by plant pathogens. These plant pathogens include tomato wilt fungi belonging to the genus Fusarium.
moxysporum f, sp, Ii-co
persici), Japanese radish fungus (Fusari)
umoxysporurn f, sp, rapha
ni), cucumber vine disease control (Fusarium oxy)
sprum f, sp, cucumerinum)
Fusarium oxysporu
m f, sp.
ｎｉｖｅｕｍ ） 、キャベツ要員病菌（Ｆｕｓａｒｉ
ｕｍ ｏｘ−ｙｓｐｏｒｕｍ ｆ、 ｓｐ、 ｃｏｎｇ
ｌｕｔｉｎａｎｓ ）、イテゴ要員病菌（Ｆｕｓａｒｉ
ｕｍ ｏｘｙｓｐｏｒｕｍ ｆ、 ｓｐ、 ｆｒａｇａ
ｒｉａｅ）コムギ紅色雪腐病菌（Ｆｕｓａｒｉｕｍ ｎ
１ｖａｌｅ ｆ、ｓｐａｇｒａｍｉｎｉｃｏｌａ）、コ
ムギ赤かび病菌（Ｆｕｓａｒｉｕｍｒｏｓｅｕｍ ｆ、
ｓｐ、 ｃｅｒｅａｌｉｓ）、エントウ根腐病菌（Ｆ
ｕｓａｒｉｕｍ ５ｏｌａｎｉ ｆ、 ｓｐ、 ｐｉｓ
ｉ）、ワタ立枯病菌、（Ｆｕｓａｒｉｕｍ ｏｘｙｓｐ
ｏｒｕｍ ｆ、 ｓｐ、 ｖａｓｉｎｆｅｃｔｕｍ）、
イネ馬鹿苗病菌（Ｆｕｓａｒｉｕｍ ｍｏｎｉｌｉｆｏ
ｒｍｅ） 、ピシウム属のキュウリ苗立枯病菌（Ｐｙｔ
ｈｉｕｍ ａｐ−ｈａｎｉｄｅｒｍａｔｕｍ）、タバコ
苗立枯病菌（Ｐｙｔｈｉｕｍｄｅｂａｒｙａｎｕｍ）
、リゾクトニア属のキュウリ苗立枯病菌・ジャガイモ黒
あざ病菌・テンサイ根腐病菌・シバ葉腐病菌・タバコ腰
折病菌（Ｒｈｉｚ−ｏｃｔｏｎｉａ ５ｏｌａｎｉ）、
テンサイ立枯病菌（Ｒｈｉｚ−ｏｃｔｏｎｉａ ｃａｎ
ｄｉｄａ）、ダイズ炭腐病菌（Ｒ，ｈｉｚｏ −ｃｔｏ
ｎｉａ ｂａｔａｔｉｃｏｌａ） 、パーティシリウム
属のナス半身萎ちょう病菌・ハクサイ買上病菌（Ｖｅｒ
ｔｉｃｉ−１１ｉｕｍ ａｌｂｏ−ａｔｒｕｍ） 、ウ
ド萎らよう病菌（Ｖｅｒｔｉ−１ｃｉｌｌｕｍ ｄａｈ
ｌｉａｅ） 、コルティシウム属のインゲン白組病菌（
Ｃｏｒｔｉｃｉｕｍ ｒｏｌｆｓｉｉ） 、テ、ｆフ・
う属のコムギ雪腐菌核病菌・アルファルファ雪腐小粒菌
核病菌（Ｔｙｐｈｕｌａ １ｎｃａｒｎａｔａ、Ｔｙｐ
ｈｕｌａ １ｓｈｉｋａｒｉｅｎｓｉｓ）１、ブラズモ
ディオフォーラ属のハクサイ根瘤病菌・キャベツ根瘤病
菌（Ｐ ｌａｓｍｏｄｉｏｐｈｏｒａｂｒａｓｓｉｃａ
ｅ）等があげラレル。niveum), cabbage cabbage fungus (Fusari)
um ox-ysporum f, sp, cong
lutinans), Fusari
um oxysporum f, sp, fraga
riae) Wheat red snow rot fungus (Fusarium n.
1vale f, spagraminicola), wheat Fusarium roseum f,
sp.
usarium 5olani f, sp, pis
i), cotton damping-off fungus, (Fusarium oxysp
orum f, sp, vasinfectum),
Fusarium monilifo
rme), cucumber seedling blight fungus of the genus Pythium (Pyt
hium ap-hanidermatum), tobacco seedling damping-off fungus (Pythium debaryanum)
, Rhizoctonia genus cucumber seedling blight fungus, potato black bruise fungus, sugar beet root rot fungus, Shiba leaf rot fungus, tobacco hip buckling fungus (Rhiz-octonia 5olani),
Rhiz-octonia can
dida), soybean charcoal rot fungus (R, hizo-cto
nia bataticola), Particillium genus eggplant half wilt and Chinese cabbage leaf wilt (Ver.
tici-11ium albo-atrum), Verti-1cillum dah
liae), Corticium sp.
Corticium rolfsii), te, ffu・
Typhula 1ncarnata (Typhula 1ncarnata, Typhula 1ncarnata)
hula 1shikariensis) 1, Chinese cabbage root-knot fungus and cabbage root-knot fungus of the genus Blasmodiophora (P lasmodiophora brassica)
e) Etc. is rarel.
本発明化合物は、一般式
％式％（１）
〔式中、Ｘは前記と同じ意味を表わす。〕で示されるア
ゾールと、これに対し、１〜１．１当量の一般式
〔式中、ｎは前記と同じ意味を表わす。〕で示されるシ
クロアルケニルイソシアナートとを、触媒として三級ア
ミンの存在下または非存在下、溶媒中または無溶媒で、
Ｏ″Ｃ〜１５０°Ｃ，１時間〜２４時間反応させること
によって製造することができる。The compound of the present invention has the general formula % (1) [wherein, X represents the same meaning as above]. ] and 1 to 1.1 equivalents of the azole represented by the general formula [wherein n represents the same meaning as above. ] in the presence or absence of a tertiary amine as a catalyst, in a solvent or without a solvent,
It can be produced by reacting at O''C to 150C for 1 to 24 hours.
溶媒としては、ヘキサン、ヘプタン、リグロイン、石油
エーテル等の脂肪族炭化水素類、ベンゼン、トルエン、
キシレン等の芳香族炭化水素類、クロロホルム、四塩化
炭素、ジクロロエタン、クロロベンゼン、ジクロロベン
ゼン等のハロゲン化炭化水素類、ジエチルエーテル、ジ
イソプロピルエーテル、ジオキサン、テトラヒドロフラ
ン、エチレングリコール、ジメチルエーテル等のエーテ
ル類、ニトロエタン、ニトロベンゼン等のニトロ化物、
アセトニトリル、イソブチロニトリル等のニトリル類、
ホルムアミド、Ｎ、Ｎ−ジメチルホルムア史ド、Ｎ、Ｎ
−ジメチルアセトアミド等の酸アミド類、ジメチルスル
ホキシド、スルホラン等の硫黄化合物等あるいは、それ
らの混合物があげられる。As a solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, benzene, toluene,
Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol, dimethyl ether, nitroethane, Nitrated compounds such as nitrobenzene,
Nitriles such as acetonitrile and isobutyronitrile,
Formamide, N, N-dimethylformamide, N, N
-Acid amides such as dimethylacetamide, sulfur compounds such as dimethylsulfoxide and sulfolane, and mixtures thereof.
触媒としての三級アミンとしては、ピリジン、トリエチ
ルアミン、Ｎ、Ｎ−ジエチルアニリン等があげられる。Examples of the tertiary amine as a catalyst include pyridine, triethylamine, N,N-diethylaniline, and the like.
反応終了後は、析出する結晶を炉別するかまたは反応液
を濃縮する等の通常の後処理を行い、必要ならば、クロ
マトグラフィー、再結晶等の操作によって精製すること
により、目的の本発明化合物を得ることができる。After the reaction is completed, the precipitated crystals are subjected to normal post-treatments such as separation in a furnace or concentration of the reaction solution, and if necessary, purification by operations such as chromatography and recrystallization is performed to obtain the objective of the present invention. compound can be obtained.
次に、上記一般式（１）で示される本発明化合物のいく
つかを示す。Next, some of the compounds of the present invention represented by the above general formula (1) will be shown.
１−（Ｎ−（２−ｖクロヘキセニル）カルバモイルクイ
ミダゾール
１−（Ｎ−（２−シクロへブテニル）カルバモイルクイ
ミダゾール
１−（Ｎ−（２−シクロヘキセニル）カルバモイル〕ベ
ンズイミダゾール
１−（Ｎ−（２−シクロヘプテニル）カルバモイル〕ベ
ンズイミダゾール
１−ＣＮ−（２−シクロヘキセニル）カルバモイル〕ベ
ンゾトリアゾール
１−（Ｎ−（２−シクロへブテニル）カルバモイル〕ベ
ンゾトリアゾール
１−（：Ｎ−（２−シクロヘキセニル）カルバモイル〕
ピラゾール
１−（Ｎ−（２−シクロへブテニル）カルバモイル〕ピ
ラゾール
１−（Ｎ−（２−シクロヘキセニル）カルバモイル）
ＩＩＬ４ ）リアゾール１−（Ｎ−（２−シクロへ
ブテニル）カルバモイル）−１，２，４−）リアゾール
１−（Ｎ−（２−シクロヘキセニル）カルバモイルクー
６−二トロインダゾール
１−（Ｎ−（２−シクロへブテニル）カルバモイルクー
６−二トロインダゾール
１−（Ｎ−（２−シクロヘキセニル）カルバモイルジ−
２−メチルイミダゾール
１−（Ｎ−（２−シクロへブテニル）カルバモイルシー
２−メチルイミタソール
１−（Ｎ−（２−シクロへキセニル）カルバモイルシー
２−メチルチオベンズイミダゾール１−（Ｎ−（２−シ
クロヘプテニル）カルバモイルシー２−メチルテオベン
ズイミグゾール１−（Ｎ−（２−シクロへキセニル）カ
ルバモイルクー５−クロロベンズイミダゾール１−（Ｎ
−（２−シクロへブテニル）カルバモイルクー５−クロ
ロベンズイミダゾール１−（Ｎ−（２−シクロへキセニ
ル）カルバモイルシー６−二トロベンズイミダゾール１
−（Ｎ−（２−シクロへブテニル）カルバモイルツー５
−二トロペンズイミダゾール１−（Ｎ−（２−シクロへ
キセニル）カルバモイルツー２−メチルベンズイミダゾ
ール１−（Ｎ−（２−シクロヘプテニル）カルバモイル
ツー２−メチルベンズイミダゾール１−（Ｎ−（２−シ
クロペンテニル）カルバモイルツー２−メチルベンズイ
ミダゾール１−（Ｎ−（２−シクロヘキセニル）カルバ
モイル）−４，５−ジクロロイミダゾール１−ＣＮ−（
２−シクロへキセニル）カルバモイルクー２−イソプロ
ピル−５−二トロイ゛定ダゾール
１−（Ｎ−（２−シクロヘキセニル）カルバモイルシー
２−エチルイ疋ダゾール
１−ＣＮ−（２−シクロヘキセニル）カルバモイルツー
２−二トロイミダゾール
１−（：Ｎ−（２−シクロへキセニル）カルバモイルク
ー５−クロロベンゾトリアゾール１−ＣＮ −（２−シ
クロヘキセニル）カルバモイルクー４−二トロイミダゾ
ール
１−（Ｎ−（２−シクロヘキセニル）カルノ（暑
モイル）−２，４，５−トリクロロイミダゾ−。1-(N-(2-vchlorohexenyl)carbamoylquimidazole 1-(N-(2-cyclohebutenyl)carbamoylquimidazole 1-(N-(2-cyclohexenyl)carbamoyl)benzimidazole 1-(N- (2-cycloheptenyl)carbamoyl]benzimidazole 1-CN-(2-cyclohexenyl)carbamoyl]benzotriazole 1-(N-(2-cyclohebutenyl)carbamoyl]benzotriazole 1-(:N-(2-cyclohexenyl) ) carbamoyl]
Pyrazole 1-(N-(2-cyclohebutenyl)carbamoyl)Pyrazole 1-(N-(2-cyclohexenyl)carbamoyl)
IIL4) Riazole 1-(N-(2-cyclohebutenyl)carbamoyl)-1,2,4-) Riazole 1-(N-(2-cyclohexenyl)carbamoyl)-6-nitroindazole 1-(N-( 2-cyclohebutenyl)carbamoyl 6-nitroindazole 1-(N-(2-cyclohexenyl)carbamoyldi-
2-methylimidazole 1-(N-(2-cyclohebutenyl)carbamoylcy 2-methylimitasole 1-(N-(2-cyclohexenyl)carbamoylcy 2-methylthiobenzimidazole 1-(N-(2 -cycloheptenyl)carbamoyl 2-methyltheobenzimigzole 1-(N-(2-cyclohexenyl)carbamoyl 5-chlorobenzimidazole 1-(N
-(2-cyclohebutenyl)carbamoyl-5-chlorobenzimidazole 1-(N-(2-cyclohexenyl)carbamoyl-6-nitrobenzimidazole 1
-(N-(2-cyclohebutenyl)carbamoyl25
-nitropenzimidazole 1-(N-(2-cyclohexenyl)carbamoyl-2-methylbenzimidazole 1-(N-(2-cycloheptenyl)carbamoyl-2-methylbenzimidazole 1-(N-(2-cyclohexenyl) pentenyl)carbamoyl2-methylbenzimidazole 1-(N-(2-cyclohexenyl)carbamoyl)-4,5-dichloroimidazole 1-CN-(
2-cyclohexenyl)carbamoyl 2-isopropyl-5-ditrodazole 1-(N-(2-cyclohexenyl)carbamoyl-2-ethylidazole 1-CN-(2-cyclohexenyl)carbamoyl2 -Ditroimidazole 1-(:N-(2-cyclohexenyl)carbamoyl 5-chlorobenzotriazole 1-CN -(2-cyclohexenyl)carbamoyl 4-ditroimidazole 1-(N-(2-cyclohexenyl) hexenyl)carno(hotmoyl)-2,4,5-trichloroimidazo-.
ル
１−（Ｎ−（２−シクロヘキセニル）カルノ（モイル）
−２，４，５−）リブロモイミダゾール
１−（Ｎ−（２−シクロへキセニル）カルノ（モイルシ
ー２−ブロモ−４，５−ジクロロイミダゾール
１−（Ｎ−（２−シクロへキセニル）カル／〈モイル）
−８，５−ジメチルピラゾール１−（Ｎ−（２−シクロ
へキセニル）カルノ（モイルシー３−メチルピラゾール
１−ＣＮ−（２−シクロヘキセニル）カルｌ＜モイルツ
ー５−メチルピラゾール
１−（Ｎ−（２−シクロへキセニル）カルノくモイルシ
ー８−二トロー１．２．４−）リアゾール
１−（Ｎ−（２−シクロヘキセニル）カルノくモイルツ
ーインダゾール
１−（Ｎ−（２−シクロへキセニル）カルバモイル〕−
７−ニトロインダゾール
１−（Ｎ−（２−シクロヘキセニル）カルバモイル）−
１，２，８−）リアゾール
１−（Ｎ−（２−シクロへキセニル）カルバモイルシー
２−クロロベンズイミダゾール１−〔Ｎ−（２−シクロ
ヘキセニル）カルバモイルシー５−二トロインタソール
１−ＣＮ−（２−シクロヘキセニル）カルバモイルクー
２−イソプロピルイミダゾール次に本発明化合物の製造
例を示す。1-(N-(2-cyclohexenyl)carno(moyl)
-2,4,5-)ribromoimidazole 1-(N-(2-cyclohexenyl)carno(moylcy 2-bromo-4,5-dichloroimidazole 1-(N-(2-cyclohexenyl)carno/ (Moyle)
-8,5-dimethylpyrazole 1-(N-(2-cyclohexenyl)carno(moylcy3-methylpyrazole1-CN-(2-cyclohexenyl)carl<moyl2-5-methylpyrazole1-(N-( 2-cyclohexenyl) carnocoumoyl 8-nitro 1.2.4-) riazole 1-(N-(2-cyclohexenyl)carnocoumoyl2indazole 1-(N-(2-cyclohexenyl)carbamoyl ]−
7-Nitroindazole 1-(N-(2-cyclohexenyl)carbamoyl)-
1,2,8-) Riazole 1-(N-(2-cyclohexenyl)carbamoylcy 2-chlorobenzimidazole 1-[N-(2-cyclohexenyl)carbamoylcy 5-nitrointasol 1-CN- (2-Cyclohexenyl)carbamoyl 2-isopropylimidazole Next, a production example of the compound of the present invention will be shown.
製造例１ 〔本発明化合物（１）の製造〕イミダゾール
０．６８９，２−シクロヘプテニルイソシアネートｘ、
ｓｒｙおよびクロロホルム５０ｇ／の混合物を室温で１
２時間撹拌した。反応液を濃縮し、残渣をシリカゲルカ
ラム（溶出液 ｎ−ヘキサン：酢酸エチル＝１：８）に
て精製し、１−（Ｎ−（２−シクロヘプテニル）カルバ
モイルコイミダゾール１、 ｔ ｏ ｙを得た。ｎ、１
．６４８９製造例２ 〔本発明化合物（１８）の製造〕
２−メチルベンズイミダゾール０．７９９１２−シクロ
へキセニルイソシアネート０．７４１およびクロロホル
ム５０ｍ１の混合物を室温で１２時間撹拌した。反応液
を濃縮し、残渣をｎ−ヘキサン：酢酸エチル＝ｌ：１に
て再Ｍ晶Ｌｔ、１ （Ｎ −（２−シクロヘキセニル
）カルバモイルツー２−メチルベンズイミダゾール０．
２１ｆを得た。ｍ、ｐ、 １０７．７°Ｃ上記製造例に
従って製造される本発明化合物のいくつかを第１表に示
す。Production Example 1 [Production of compound (1) of the present invention] Imidazole 0.689,2-cycloheptenyl isocyanate x,
sry and 50 g/chloroform at room temperature.
Stirred for 2 hours. The reaction solution was concentrated, and the residue was purified with a silica gel column (eluent: n-hexane:ethyl acetate = 1:8) to obtain 1-(N-(2-cycloheptenyl)carbamoylcoimidazole 1, toy). .n, 1
．． 6489 Production Example 2 [Production of compound (18) of the present invention]
A mixture of 0.79911 2-methylbenzimidazole, 0.741 2-cyclohexenyl isocyanate and 50 ml of chloroform was stirred at room temperature for 12 hours. The reaction solution was concentrated, and the residue was recrystallized with n-hexane:ethyl acetate=l:1.
21f was obtained. m, p, 107.7°C Some of the compounds of the present invention produced according to the above production examples are shown in Table 1.
第 １ 表
本発明化合物を土壌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用いてもよ
いが、通常固体担体、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、水溶剤、微粒剤等に製剤する。Table 1 When the compound of the present invention is used as an active ingredient in a soil disease control agent, it may be used as it is without adding any other ingredients, but it is usually used in combination with a solid carrier, liquid carrier, surfactant, or other formulation aid. By mixing with agents, emulsions, wettable powders, suspensions, granules,
Formulate into powder, aqueous solution, fine granules, etc.
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０、２〜８０．０
％含有する。These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 99.9%, preferably 0.2 to 80.0%.
%contains.
上述の固体担体としては、カオリンクレー、アッタパル
ジャイトクレー、ベントナイト、酸性白土、ノぐイロフ
ィライト、タルク、珪藻土、方解石、トウモロコシ穂軸
粉、クルミ般粉、尿素、硫酸アンモニウム、合成含水酸
化硅素等の微粉末あるいは粒状物があげられ、液体担体
としては、キシレン、メチルナフタレン等の芳香族炭化
水素、イソプロパツール、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、水等があげられる
。また、乳化、分散、湿展等のために用いられる界面活
性剤としては、アルキル硫酸エステル塩’、７ＪＬ／キ
ル硫酸エステル塩、アルキル（アリール）スルホン酸塩
、ジアルキルスルホコハク酸塩、ポリオキシエチレンア
ルキルアリールエーテルリン酸エステル塩、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ックコポリマー、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げられる
。製剤用補助剤としては、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、ＣＭ
Ｃ（カルボキシメチルセルロース）、ＰＡＰ（酸性り：
／酸イソプロピル）等があげられる。The solid carriers mentioned above include fine particles such as kaolin clay, attapulgite clay, bentonite, acid clay, nogyrophyllite, talc, diatomaceous earth, calcite, corn cob flour, walnut flour, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, soybean oil, cottonseed oil, etc. Examples include vegetable oil, dimethyl sulfoxide, acetonitrile, water, etc. In addition, surfactants used for emulsification, dispersion, wetting, etc. include alkyl sulfate salts, 7JL/kyl sulfate salts, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl Anionic surfactants such as aryl ether phosphate ester salts, naphthalene sulfonic acid formalin condensates,
Examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. As formulation aids, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CM
C (carboxymethylcellulose), PAP (acidic acid:
/isopropyl acid), etc.
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。部は重量部を表わす。Examples of formulations are shown below. The compounds of the present invention are indicated by compound numbers in Table 1. Parts represent parts by weight.
製剤例１
化合物（１）２部、カオリンクレー８８部およびタルク
１０部をよく粉砕混合して粉剤を得る。Formulation Example 1 2 parts of compound (1), 88 parts of kaolin clay, and 10 parts of talc are thoroughly ground and mixed to obtain a powder.
製剤例２
化合物（８）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８０部およびカ
オリンクレー６６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。Formulation Example 2 2 parts of compound (8), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 80 parts of bentonite and 66 parts of kaolin clay were thoroughly ground and mixed, water was added and the mixture was thoroughly kneaded, followed by granulation. Dry to obtain granules.
製剤例８
化合物（５） ５０部、リグニンスルホン酸カルシウム
８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（粉砕混合して水和剤を得る。Formulation Example 8 50 parts of compound (5), 8 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are ground and mixed to obtain a wettable powder.
製剤例４
化合物（８） １０部、ポリオキシエチレンスチリルフ
ェニルエーテル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８０部およびインプロパツール
４０部をよ（混合して札割を得る。Formulation Example 4 10 parts of compound (8), 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 80 parts of xylene, and 40 parts of Impropatol were mixed to obtain a bill.
製剤例５
化合物（１１） ８０部をジメチルスルホキシドに混和
溶解し、アッタバルジャイトクレー７０部に吸着、含浸
した後、乾燥して微粒剤を得る。Formulation Example 5 80 parts of compound (11) is mixed and dissolved in dimethyl sulfoxide, adsorbed and impregnated with 70 parts of attabulgite clay, and then dried to obtain fine granules.
製剤例６
化合物（１８） １０部、ポリオキシエチレンスチリル
フェニルエーテル１部、水８９部を混合し、液剤を得る
。Formulation Example 6 10 parts of compound (18), 1 part of polyoxyethylene styrylphenyl ether, and 89 parts of water are mixed to obtain a liquid preparation.
これらの製剤例はそのままで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、他の土壊病害防
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。These formulation examples are used as they are or diluted with water, etc., and treated with foliage or soil. For soil treatment, the preparation can be applied to the soil surface (if necessary, mixed with the soil after application) or irrigated into the soil. Furthermore, by mixing it with other soil damage control agents, it can be expected to increase the control efficacy. Furthermore, it can be used in combination with fungicides, soil pest control agents, nematicides, plant growth regulators, fertilizers, soil conditioners, and the like.
なお、本発明化合物は、畑地、水田、果樹園。The compound of the present invention can be used in fields, paddy fields, and orchards.
茶畑、桑畑、牧草地、芝生地等の土壌病害防除剤の有効
成分として用いることができる。It can be used as an active ingredient in soil disease control agents for tea fields, mulberry fields, pastures, lawns, etc.
本発明化合物を除草剤の有効成分として用いる場合、そ
の処理量は、気象条件、製剤形態、処理時期、方法、場
所、対象雑草、対象作物等によ７ても異なるが、通常１
０アールあたりｏ、ｏｏｔｋｇ〜５０ ｋｇ、好ましく
は、０．０１ ｋｇ〜１０＃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０．０００５〜６．０％、好ましくは
０．００５〜０．５％である。When the compound of the present invention is used as an active ingredient of a herbicide, the amount to be treated will vary depending on weather conditions, formulation form, treatment time, method, location, target weeds, target crops, etc., but usually 1.
o, ootkg to 50 kg per 0 are, preferably 0.01 kg to 10 kg, and granules, powders, fine granules, etc. are applied as they are without any dilution, and emulsions,
When applying a wettable powder, suspending agent, aqueous solvent, etc. diluted with water, the applied concentration is 0.0005 to 6.0%, preferably 0.005 to 0.5%.
次に、本発明化合物が土壌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、比較対照に用いた化合物は
第２表の化合物記号で示す。Next, test examples demonstrate that the compound of the present invention is useful as an active ingredient of a soil disease control agent. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.
第 ２ 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、根等の菌叢、磨機の程度を肉眼観察し、菌叢、
磨機が全く認められない供試植物数（以下、健苗数と記
す。）について、化合物を供試した場合（以下、処理区
の健苗数と記す。）と、化合物を供試せずかつ病原菌を
全く接極していない場合（以下、無処理、無接種区の健
苗数と記す。）とをそれぞれ数え、次式に従って健苗率
（％）を求めて、その数値で示す。Table 2 In addition, the control efficacy was determined by visual observation of the diseased state of the test plants at the time of the survey, that is, the bacterial flora of leaves, stems, roots, etc., and the degree of polishing.
Regarding the number of test plants for which the polishing machine was not recognized at all (hereinafter referred to as the number of healthy seedlings), there were two cases in which the compound was tested (hereinafter referred to as the number of healthy seedlings in the treatment area), and a case where the compound was not used and Count the number of healthy seedlings in the case where no pathogens are attached at all (hereinafter referred to as the number of healthy seedlings in the untreated and non-inoculated area), calculate the healthy seedling rate (%) according to the following formula, and indicate the number.
試験例１ ダイコン要員病試験（予防効果）プラスチッ
クポットに畑地土壌とダイコン要員病菌と培養した病原
土壌を良く混合して詰めた。ダイコン（品種：早生４０
日）を１５粒播種し覆土した。その後、製剤例３に準じ
て水和剤にした供試化合物の所定量を水で希釈し、土壌
潅注した。温室内で８週間育成し、防除効力を調査した
。Test Example 1 Radish radish disease test (preventive effect) Upland soil, radish disease bacteria, and pathogenic soil cultured were mixed well and packed in a plastic pot. Daikon (variety: early 40)
15 seeds were sown and covered with soil. Thereafter, a predetermined amount of the test compound made into a hydrating powder according to Formulation Example 3 was diluted with water and watered into the soil. The plants were grown in a greenhouse for 8 weeks and their pesticidal efficacy was investigated.
結果を第８表に示す。The results are shown in Table 8.
第 ８ 表
試験例２ ダイコン要員病試験（残効性試験）試験例１
に準じて４週間育成し、防除効力を調査した。結果を第
４表に示す。Table 8 Test Example 2 Radish personnel disease test (residual effect test) Test Example 1
The plants were grown for 4 weeks according to the method described above, and their pesticidal efficacy was investigated. The results are shown in Table 4.
第 ４ 表
試験例８ キュウリ蔓割病防除効果
プラスチックポットに畑地土壌を詰め、キュウリ蓋側病
菌を培養した病原土壌と製剤例１に醜して粉剤にした供
試化合物の所定量を表層５儒の深さまで良く混合して詰
めた。なお、ヒドロキシイソキジゾールについては、畑
地土壌を詰めたポットに所定量を水で希釈して潅注した
。キュウリ（品ｉ：ｍ不和地道）を１０粒播種し覆土し
た。温室内で８週間育成し、防除効力を調査した。Table 4 Test Example 8 Cucumber vine disease control effect A plastic pot was filled with field soil, and a predetermined amount of the test compound made into a powder was added to the pathogenic soil in which the cucumber lid disease fungus was cultured and Formulation Example 1 for 5 hours on the surface. Mix well and pack to a depth of . Regarding hydroxyisokidizole, a predetermined amount was diluted with water and watered into a pot filled with field soil. Ten seeds of cucumber (product I: m Fuwajido) were sown and covered with soil. The plants were grown in a greenhouse for 8 weeks and their pesticidal efficacy was investigated.
結果を第５表に示す。The results are shown in Table 5.
第 ５ 表
試験例４ トマト萎ちょう病防除効果
製剤例４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、プラスチックポットで育成した
８葉期のトマト苗（品種：福寿２号）の葉面に充分付着
するように散布した。散布後、トマト萎ちょう病菌の胞
子懸濁液を根元に潅注接種した。接種後、温室内で８週
間育成し、防除効力を調査した。Table 5 Test Example 4 Tomato wilt control effect A test compound made into an emulsion according to Preparation Example 4 was diluted with water to a specified concentration, and it was added to 8-leaf stage tomato seedlings (cultivars) grown in plastic pots. : Fukuju No. 2) was sprayed so that it adhered sufficiently to the leaf surface. After spraying, a spore suspension of the tomato wilt fungus was inoculated at the roots by irrigation. After inoculation, they were grown in a greenhouse for 8 weeks and their control efficacy was investigated.
結果を第６表に示す。The results are shown in Table 6.
第 ６ 表
試験例５ ナス半身萎ちょう病防除効果ナス半身萎ちょ
う病菌を培養したふすま培地を１区（２ｍ）ｔｖ）たり
１００Ｎ！３．種し、製剤飢５に準じて微粒剤にし・た
供試化合物の所定量を土壌に混和した。なお、クロルピ
クリンは、病原ｉを接種後、その所定量を注入しビニー
ル被′８ｙシて１週間放置し、ビニール被覆を除去しで
耕耘し、さらに１週間ガス抜きをした。その後、２葉期
のナス（品種；千両２号）を１区ｒ％たり１６本移植し
、温室内で約６週間育成１ノ、防除効力を調査した。Table 6 Test Example 5 Effect on controlling eggplant half-body wilt disease One area (2 m) of bran medium cultured with eggplant half-body wilt fungus was heated to 100 N! 3. A predetermined amount of the test compound, which was seeded and made into fine granules according to Formulation 5, was mixed into the soil. For chloropicrin, after inoculating the pathogen I, a predetermined amount of it was injected, covered with vinyl for 8 years, left for one week, the vinyl coating was removed and cultivated, and degassed for another week. Thereafter, 16 two-leaf eggplants (variety: Senryo No. 2) were transplanted per plot r%, grown in a greenhouse for about 6 weeks, and their pesticidal efficacy was investigated.
結果を第７表に示す。The results are shown in Table 7.
第 ７ 表
試験例６ ハクサイ根瘤病防除効果
プラスチックポットに畑地土壌を詰め、ハクサイ根瘤病
菌で汚染された土壌と製剤例１にｉＪｌじて粉剤にした
供試化合物の所定量を表層５備の深さまで良く混合して
詰めた。ハクサイ（品ａ：耐病６０日）を１５粒１種し
要！±した。温室内で４週間育成し、防除効力を調査し
た。Table 7 Test Example 6 Effect on Chinese cabbage root-knot control A plastic pot was filled with field soil, and a predetermined amount of the soil contaminated with Chinese cabbage root-knot bacteria and a test compound made into a powder according to Preparation Example 1 was added to a depth of 500 ml to the surface layer. Mix well and pack. One type of 15 Chinese cabbage (product A: disease resistance 60 days) is required! ± did. The plants were grown in a greenhouse for 4 weeks and their pesticidal efficacy was investigated.
結果を第８表に示す。The results are shown in Table 8.
第 ８ 表
試験例７ ワタ立枯病防除試験
プラスチックポットに畑土壌とワタ立枯病菌を培養した
病原土壌を詰め、その上に製剤例３に準じて水和剤にし
た供試化合物の所定量を粉衣したワタ（品種： Ｃｏｋ
ｅｒ）を１０粒播種し、覆土した。温室内で８週間育成
し、防除効力を調査した。Table 8 Test Example 7 Cotton damping-off control test A plastic pot is filled with field soil and pathogenic soil in which cotton damping-off fungi have been cultured, and a predetermined amount of the test compound made into a hydrating powder according to Formulation Example 3 is placed on top of the pot. Cotton coated with flour (variety: Cok
er) were sown and covered with soil. The plants were grown in a greenhouse for 8 weeks and their pesticidal efficacy was investigated.
結果を第９表に示す。The results are shown in Table 9.
第 ９ 表Table 9
Claims (1)
ール−１−イル基またはインダ ゾール−１−イル基を表わし、ｎは１から ３までの整数を表わす。〕 で示されるシクロアルケニルアミド誘導体。 （２）一般式 Ｘ−Ｈ 〔式中、Ｘはハロゲン原子、低級アルキル 基、ニトロ基、低級アルキルチオ基よりな る置換基で置換されていてもよいイミダゾ ール−１−イル基、ベンズイミダゾール− １−イル基、ベンゾトリアゾール−１−イ ル基、ピラゾール−１−イル基、１，２，４−トリアゾ
ール−１−イル基またはインダ ゾール−１−イル基を表わす。〕 で示されるアゾールと一般式 ▲数式、化学式、表等があります▼ 〔式中、ｎは１から３の整数を表わす。〕 で示されるシクロアルケニルイソシアナートとを反応さ
せることを特徴とする一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｘおよびｎは前記と同じ意味を表 わす。〕 で示されるシクロアルケニルアミド誘導体の製造法。 （８）一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｘはハロゲン原子、低級アルキル 基、ニトロ基、低級アルキルチオ基よりな る置換基で置換されていてもよいイミダゾ ール−１−イル基、ベンズイミダゾール− １−イル基、ベンゾトリアゾール−１−イ ル基、ピラゾール−１−イル基、１，２，４−トリアゾ
ール−１−イル基またはインダ ゾール−１−イル基を表わし、ｎは１から ３までの整数を表わす。〕 で示されるシクロアルケニルアミド誘導体を有効成分と
する土壌病害防除剤。[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. Good imidazol-1-yl group, benzimidazol-1-yl group, benzotriazol-1-yl group, pyrazol-1-yl group, 1,2,4-triazol-1-yl group or indazol-1-yl group , and n represents an integer from 1 to 3. ] A cycloalkenylamide derivative represented by (2) General formula X-H [wherein, yl group, benzotriazol-1-yl group, pyrazol-1-yl group, 1,2,4-triazol-1-yl group or indazol-1-yl group. ] The azole shown by and the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, n represents an integer from 1 to 3. ] There are general formulas ▲ numerical formulas, chemical formulas, tables, etc. ▼ which are characterized by reacting with cycloalkenyl isocyanate shown by ▼ [In the formula, X and n represent the same meanings as above. ] A method for producing a cycloalkenylamide derivative. (8) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, group, benzimidazol-1-yl group, benzotriazol-1-yl group, pyrazol-1-yl group, 1,2,4-triazol-1-yl group or indazol-1-yl group, and n is 1 Represents an integer from to 3. ] A soil disease control agent containing a cycloalkenylamide derivative shown as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60177977A JPS6239573A (en) | 1985-08-13 | 1985-08-13 | Cycloalkenylamide derivative, production thereof and soil blight controlling agent containing said derivative as active constituent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60177977A JPS6239573A (en) | 1985-08-13 | 1985-08-13 | Cycloalkenylamide derivative, production thereof and soil blight controlling agent containing said derivative as active constituent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6239573A true JPS6239573A (en) | 1987-02-20 |
Family
ID=16040380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60177977A Pending JPS6239573A (en) | 1985-08-13 | 1985-08-13 | Cycloalkenylamide derivative, production thereof and soil blight controlling agent containing said derivative as active constituent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6239573A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007045393A1 (en) * | 2005-10-19 | 2007-04-26 | Sanofi-Aventis | Carbamoylbenzotriazole derivatives as inhibitors of lipases and phospholipases |
-
1985
- 1985-08-13 JP JP60177977A patent/JPS6239573A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007045393A1 (en) * | 2005-10-19 | 2007-04-26 | Sanofi-Aventis | Carbamoylbenzotriazole derivatives as inhibitors of lipases and phospholipases |
| US7897625B2 (en) | 2005-10-19 | 2011-03-01 | Sanofi-Aventis | Carbamoylbenzotriazole derivatives as inhibitors of lipases and phospholipases |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6250465B2 (en) | ||
| US4902705A (en) | Imidazole derivatives, an antibacterial and antifungal agent comprising said derivatives, and a process for the production of said imidazole derivatives | |
| JPS61126071A (en) | Phenoxyisobutyric acid amide derivative, and agricultural and horticultural fungicide | |
| BG62077B1 (en) | New 3-phenylpyrazol derivatives and their application as fungicides | |
| JPS6139941B2 (en) | ||
| JPH0333701B2 (en) | ||
| JPS60166665A (en) | Tetrahydro-2h-indazole derivative, preparation thereof and herbicide containing same as active constituent | |
| US4146646A (en) | Bis-amide fungicidal compounds | |
| US4500536A (en) | Derivatives of N,N'-substituted azolecarboxamide and agricultural and horticultural fungicidal or nematicidal composition containing same as active ingredients | |
| NO862231L (en) | FUNGICIDE AGENTS. | |
| JPS6239573A (en) | Cycloalkenylamide derivative, production thereof and soil blight controlling agent containing said derivative as active constituent | |
| US4481027A (en) | Derivatives of tetrahydrobenzothiazole and herbicidal compositions _containing the same as an active ingredient | |
| JPS601315B2 (en) | Imidazole derivatives, their production methods, and agricultural and horticultural fungicides | |
| JPS62103081A (en) | Dioxolanilmethyltriazone, agricultural and horticultural fungicide, plant growth regulator and herbicide comprising same as active ingredient | |
| US5110827A (en) | Imidazole compounds having fungicidal activity | |
| KR100314196B1 (en) | Agricultural Horticultural Fungicide Composition | |
| JPH0368573A (en) | Azolidine derivative, its production and fungicide for agricultural and horticultural use | |
| JPS58150590A (en) | Novel n,n'-substituted azolecarboxamide derivative and agricultural and horticultural fungicide containing it as active ingredient | |
| JPS62103067A (en) | Pyrazole derivative, production thereof, and herbicide and agricultural and horticultural fungicide containing same | |
| JPS6121553B2 (en) | ||
| JPH027563B2 (en) | ||
| JPH01250379A (en) | Amide derivative, its production and agricultural and horticultural fungicide containing said derivative as active component | |
| CH631602A5 (en) | Microbicides | |
| JPH04178362A (en) | Urea derivative and pest controlling agent containing the same | |
| JPH0285282A (en) | Azole derivative and germicide for agriculture and horticulture |