JP2004161646A - Fungicide composition for agriculture and horticulture - Google Patents
Fungicide composition for agriculture and horticulture Download PDFInfo
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- JP2004161646A JP2004161646A JP2002327898A JP2002327898A JP2004161646A JP 2004161646 A JP2004161646 A JP 2004161646A JP 2002327898 A JP2002327898 A JP 2002327898A JP 2002327898 A JP2002327898 A JP 2002327898A JP 2004161646 A JP2004161646 A JP 2004161646A
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- compound
- alkyl
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- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 239000000417 fungicide Substances 0.000 title claims abstract description 15
- 238000003898 horticulture Methods 0.000 title abstract description 4
- -1 cyanomethylene compound Chemical class 0.000 claims abstract description 125
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 18
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229930182558 Sterol Natural products 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- 150000003432 sterols Chemical class 0.000 claims abstract description 8
- 235000003702 sterols Nutrition 0.000 claims abstract description 8
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 claims description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 150000008059 anilinopyrimidines Chemical class 0.000 claims description 4
- 150000002357 guanidines Chemical class 0.000 claims description 4
- 150000002780 morpholines Chemical class 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- IRTLROCMFSDSNF-UHFFFAOYSA-N 2-phenyl-1h-pyrrole Chemical compound C1=CNC(C=2C=CC=CC=2)=C1 IRTLROCMFSDSNF-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 230000029058 respiratory gaseous exchange Effects 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 10
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 230000009969 flowable effect Effects 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000000241 respiratory effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005730 Azoxystrobin Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000005747 Chlorothalonil Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000005778 Fenpropimorph Substances 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 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
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 2
- 150000008056 dicarboxyimides Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 244000053095 fungal pathogen Species 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000003915 liquefied petroleum gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000008060 phenylpyrroles Chemical class 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- 125000004790 1-fluoroethoxy group Chemical group FC(C)O* 0.000 description 1
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
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- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- ZRADTNJSPQDCDV-UHFFFAOYSA-N 2-butyl-4-methoxyphenol Chemical compound CCCCC1=CC(OC)=CC=C1O ZRADTNJSPQDCDV-UHFFFAOYSA-N 0.000 description 1
- 125000006012 2-chloroethoxy group Chemical group 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 1
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 1
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 239000005746 Carboxin Substances 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 239000005754 Cyazofamid Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 239000005758 Cyprodinil Substances 0.000 description 1
- 239000005644 Dazomet Substances 0.000 description 1
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- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000003516 soil conditioner Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【０００１】
【発明の属する技術分野】
本発明は、農園芸用殺菌剤組成物に関する。
【０００２】
【従来の技術】
一般式（１）
【０００３】
【化２】
〔式中、ＲはＣ１−２０の直鎖もしくは分枝鎖状アルキル基、Ｃ３−８シクロアルキル基、アリール基、アリールＣ１−４アルキル基又はヘテロ環基を示す。アリール基、アリールＣ１−４アルキル基及びヘテロ環基上には、ハロゲン原子、Ｃ１−４アルキル基、Ｃ１−４ハロアルキル基、Ｃ１−４アルコキシ基、Ｃ１−４ハロアルコキシ基、Ｃ１ −４アルコキシカルボニル基、Ｃ１−４アルキルアミノカルボニル基、Ｃ１−４アルコキシイミノＣ１−４アルキル基、Ｃ１−４アルキルアミノ基、Ｃ１−４アルキルカルボニル基、Ｃ１−４アルキルチオ基、アリールＣ１−４アルキル基、カルバモイル基、フェノキシ基、ベンジルオキシ基、ニトロ基及びシアノ基から選ばれる少なくとも１種の置換基が置換していてもよい。
【０００５】
Ｒ１はＣ１−８の直鎖もしくは分枝鎖状アルキル基、Ｃ３−８シクロアルキル基、アリール基、アリールＣ１−４アルキル基又はヘテロ環基を示す。アリール基、アリールＣ１−４アルキル基及びヘテロ環基上には、ハロゲン原子、Ｃ１−４アルキル基、Ｃ１−４ハロアルキル基、Ｃ１−４アルコキシ基、Ｃ１−４ハロアルコキシ基、Ｃ１−４アルコキシカルボニル基、Ｃ１−４アルキルアミノ基、ジＣ１−４アルキルアミノ基、Ｃ２−４アルケニル基、Ｃ１−４アルキルチオ基、Ｃ１−４アルキルスルフィニル基、Ｃ１−４アルキルスルホニル基、フェニル基、フェノキシ基、ニトロ基及びシアノ基から選ばれる少なくとも１種の置換基が置換していてもよい。
【０００６】
ＡはＣ１−６の直鎖もしくは分枝鎖状アルキレン基、Ｃ２−６の直鎖もしくは分枝鎖状アルケニレン基、基−ＣＨ２−Ｂ−ＣＨ２−（Ｂはフェニレン基を示す）、基−ＣＨ２−Ｏ−Ｂ−ＣＨ２−（Ｂは前記に同じ）又は基−Ｚ−ＣＯ−（ＺはＣ１−４アルキレン基を示す）を示す。
【０００７】
Ｙは硫黄原子、スルフィニル基又はスルホニル基を示す。
【０００８】
ａは０又は１を示す。〕
で表されるシアノメチレン化合物は、殺菌活性を有する化合物として公知である（特許文献１）。
【０００９】
また、農園芸用殺菌活性を有する化合物として、ＳＨ阻害活性化合物、アクリル酸系化合物、ベンズイミダゾール系化合物、ジカルボキシイミド系化合物、グアニジン系化合物、酸アミド系化合物、アニリノピリミジン系化合物、モルホリン系化合物、ベンゾイソチアゾール系化合物、カーバメート系化合物、有機リン系化合物、ステロール生合成阻害活性化合物、フェニルピロール系化合物、呼吸阻害系化合物等の多くの化合物が開発され、使用されている（非特許文献１〜非特許文献４）。
【００１０】
今日まで、上記一般式（１）で表されるシアノメチレン化合物とこれら農園芸用殺菌活性を有する化合物とを組み合わせることは、具体的には知られていない。
【００１１】
ところで、農作物は、多種多様な病害虫の被害に晒される。そのために、一般に、殺菌活性化合物が有する殺菌活性能力の中で不足している部分を補うために、また該能力のレベルを向上させるために、他の殺菌活性化合物と混合して農薬製剤を開発することが試みられている。
【００１２】
しかしながら、異なる殺菌活性化合物を混合したとしても、その組み合わせによっては本来有している殺菌活性が損われたり、単なる相加効果を与えるに止まるものが殆どである。
【００１３】
【特許文献１】
ＷＯ第０１／４７９０２号公報、請求の範囲
【００１４】
【非特許文献１】
Ｐｅｓｔｉｃ． Ｓｃｉ．， ３１， ４９９−５１９（１９９１）
【００１５】
【非特許文献２】
Ｂｒｉｇｈｔｏｎ Ｃｒｏｐ Ｐｒｏｔ． Ｃｏｎｆ．−Ｐｅｓｔｓ ａｎｄ Ｄｉｓｅａｓｅｓ， ５０１−５０８（１９９４）
【００１６】
【非特許文献３】
Ｂｒｉｇｈｔｏｎ Ｃｒｏｐ Ｐｒｏｔ． Ｃｏｎｆ．−Ｐｅｓｔｓ ａｎｄ Ｄｉｓｅａｓｅｓ， ６５−７２（１９８８）
【００１７】
【非特許文献４】
Ｂｒｉｇｈｔｏｎ Ｃｒｏｐ Ｐｒｏｔ． Ｃｏｎｆ．−Ｐｅｓｔｓ ａｎｄ Ｄｉｓｅａｓｅｓ， １７−２３（１９８８）
【００１８】
【発明が解決しようとする課題】
本発明は、一般式（１）で表されるシアノメチレン化合物の殺菌活性を向上させ、該化合物の使用量を低減し、農園芸上の広範な病原菌に対して有効な殺菌剤組成物を提供することを課題とする。
【００１９】
【課題を解決するための手段】
本発明者は、上記課題を解決すべく鋭意研究を重ねた結果、一般式（１）で表されるシアノメチレン化合物と下記に示す特定の農園芸用殺菌活性化合物とを組み合わせることにより、本発明の課題を解決できることを見い出した。本発明は、斯かる知見に基づき完成されたものである。
【００２０】
即ち、本発明は、（１） 一般式（１）
【００２１】
【化３】
〔式中、Ｒ、Ｒ１、Ａ、Ｙ及びａは前記に同じ。〕
で表されるシアノメチレン化合物、並びに（２） ＳＨ阻害活性化合物、アクリル酸系化合物、ベンズイミダゾール系化合物、ジカルボキシイミド系化合物、グアニジン系化合物、酸アミド系化合物、アニリノピリミジン系化合物、モルホリン系化合物、ベンゾイソチアゾール系化合物、カーバメート系化合物、有機リン系化合物、ステロール生合成阻害活性化合物、フェニルピロール系化合物及び呼吸阻害系化合物からなる群から選ばれる少なくとも１種の農園芸用殺菌活性化合物を有効成分とする農園芸用殺菌剤組成物に係る。
【００２３】
【発明の実施の形態】
上記一般式（１）において、Ｒ、Ｒ１、Ａ及びＺで示される各基は、具体的には以下のものを挙げることができる。
【００２４】
Ｃ１−２０の直鎖もしくは分枝鎖状アルキル基としては、例えばメチル基、エチル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−ヘプチル基、ｎ−オクチル基、ｎ−ノニル基、ｎ−デシル基、ｎ−ウンデシル基、ｎ−ドデシル基、ｎ−トリデシル基、ｎ−テトラデシル基、ｎ−ペンタデシル基、ｎ−ヘキサデシル基、ｎ−ヘプタデシル基、ｎ−オクタデシル基、ｎ−ノナデシル基等を挙げることができる。
【００２５】
Ｃ３−８シクロアルキル基としては、例えばシクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基等を挙げることができる。
【００２６】
アリール基としては、例えばフェニル基、ナフチル基等を挙げることができる。
【００２７】
アリールＣ１−４アルキル基としては、例えばベンジル基、１−フェニルエチル基、２−フェニルエチル基、１−フェニルプロピル基、２−フェニルプロピル基、３−フェニルプロピル基等を挙げることができる。
【００２８】
ヘテロ環基としては、例えばピリジル基、ピリミジル基、ベンゾトリアゾリル基、１，２，４−トリアゾール−１−イル基、２−チエニル基、ピラジニル基、ピリダジニル基、２−ベンゾチアゾリル基、オキサゾリル基、イソキサゾリル基、チアゾリル基、８−キノリル基、オキサジアゾリル基等を挙げることができる。
【００２９】
ハロゲン原子としては、弗素原子、塩素原子、臭素原子、沃素原子等を挙げることができる。
【００３０】
Ｃ１−４アルキル基としては、メチル基、エチル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基等の炭素数１〜４の直鎖状又は分枝鎖状のアルキル基を挙げることができる。
【００３１】
Ｃ１−４ハロアルキル基としては、例えば、フルオロメチル基、ブロモメチル基、ヨードメチル基、ジフルオロメチル基、トリフルオロメチル基、２−フルオロエチル基、２−クロロエチル基、１−フルオロエチル基、ペンタフルオロエチル基、１−フルオロプロピル基、２−クロロプロピル基、３−フルオロプロピル基、３−クロロプロピル基、１−フルオロブチル基、１−クロロブチル基、４−フルオロブチル基等の１〜９個のハロゲン原子で置換された直鎖状又は分枝鎖状のアルキル基を挙げることができる。
【００３２】
Ｃ１−４アルコキシ基としては、例えば、メトキシ基、エトキシ基、ｎ−プロポキシ基、イソプロポキシ基、ｎ−ブトキシ基、イソブトキシ基、ｓｅｃ−ブトキシ基、ｔｅｒｔ−ブトキシ基等の炭素数１〜４の直鎖状又は分枝鎖状のアルコキシ基を挙げることができる。
【００３３】
Ｃ１−４ハロアルコキシ基としては、例えば、フルオロメトキシ基、クロロメトキシ基、ブロモメトキシ基、ヨードメトキシ基、ジフルオロメトキシ基、トリフルオロメトキシ基、２−フルオロエトキシ基、２−クロロエトキシ基、１−フルオロエトキシ基、２，２，２−トリフルオロエトキシ基、ペンタフルオロエトキシ基、１−フルオロプロポキシ基、２−クロロプロポキシ基、３−フルオロプロポキシ基、３−クロロプロポキシ基、１−フルオロブトキシ基、１−クロロブトキシ基、４−フルオロブトキシ基等の１〜９個のハロゲン原子で置換された炭素数１〜４の直鎖状又は分枝鎖状のアルコキシ基を挙げることができる。
【００３４】
Ｃ１−４アルコキシカルボニル基としては、例えば、メトキシカルボニル基、エトキシカルボニル基、ｎ−プロポキシカルボニル基、イソプロポキシカルボニル基、ｎ−ブトキシカルボニル基、イソブトキシカルボニル基、ｓｅｃ−ブトキシカルボニル基、ｔｅｒｔ−ブトキシカルボニル基等の、アルコキシ部分が炭素数１〜４の直鎖状又は分枝鎖状であるアルコキシカルボニル基を挙げることができる。
【００３５】
Ｃ１−４アルキルアミノカルボニル基としては、例えばメチルアミノカルボニル基、エチルアミノカルボニル基、ｎ−プロピルアミノカルボニル基、イソプロピルアミノカルボニル基、ｎ−ブチルアミノカルボニル基、イソブチルアミノカルボニル基、ｓｅｃ−ブチルアミノカルボニル基、ｔｅｒｔ−ブチルアミノカルボニル基等の、アルキル部分が炭素数１〜４の直鎖状又は分枝鎖状であるアルキルアミノカルボニル基を挙げることができる。
【００３６】
Ｃ１−４アルコキシイミノＣ１−４アルキル基としては、例えばメトキシイミノメチル基、エトキシイミノメチル基、１−（ｎ−プロポキシイミノ）エチル基、イソプロポキシイミノメチル基、２−（ｎ−ブトキシイミノ）エチル基、ｓｅｃ−ブトキシイミノメチル基、ｔｅｒｔ−ブトキシイミノメチル基等のアルコキシ部分が炭素数１〜４の直鎖状又は分枝鎖状であり、アルキル部分が炭素数１〜４の直鎖状又は分枝鎖状であるアルコキシイミノアルキル基を挙げることができる。
【００３７】
Ｃ１−４アルキルアミノ基としては、例えばメチルアミノ基、エチルアミノ基、ｎ−プロピルアミノ基、イソプロピルアミノ基、ｎ−ブチルアミノ基、イソブチルアミノ基、ｓｅｃ−ブチルアミノ基、ｔｅｒｔ−ブチルアミノ基等のアルキル部分が炭素数１〜４の直鎖状又は分枝鎖状であるアルキルアミノ基を挙げることができる。
【００３８】
Ｃ１−４アルキルカルボニル基としては、例えばメチルカルボニル基、エチルカルボニル基、ｎ−プロピルカルボニル基、イソプロピルカルボニル基、ｎ−ブチルカルボニル基、イソブチルカルボニル基、ｓｅｃ−ブチルカルボニル基、ｔｅｒｔ−ブチルカルボニル基等の、アルキル部分が炭素数１〜４の直鎖状又は分枝鎖状であるアルキルカルボニル基を挙げることができる。
【００３９】
Ｃ１−８の直鎖もしくは分枝鎖状アルキル基としては、例えばメチル基、エチル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−ヘプチル基、ｎ−オクチル基等を挙げることができる。
【００４０】
ジＣ１−４アルキルアミノ基としては、例えばジメチルアミノ基、ジエチルアミノ基、ジ−ｎ−プロピルアミノ基、ジイソプロピルアミノ基、ジ−ｎ−ブチルアミノ基、ジイソブチルアミノ基、ｓｅｃ−ブチルアミノ基、ジ−ｔｅｒｔ−ブチルアミノ基等のアルキル部分が炭素数１〜４の直鎖状又は分枝鎖状であるジアルキルアミノ基を挙げることができる。
【００４１】
Ｃ２−４アルケニル基としては、例えばビニル基、アリル基、イソプロペニル基、２−ブテニル基、３−ブテニル基、１−メチル−２−プロペニル基等を挙げることができる。
【００４２】
Ｃ１−４アルキルチオ基としては、例えばメチルチオ基、エチルチオ基、ｎ−プロピルチオ基、イソプロピルチオ基、ｎ−ブチルチオ基、イソブチルチオ基、ｓｅｃ−ブチルチオ基、ｔｅｒｔ−ブチルチオ基等の、アルキル部分が炭素数１〜４の直鎖状又は分枝鎖状であるアルキルチオ基を挙げることができる。
【００４３】
Ｃ１−４アルキルスルフィニル基としては、例えばメチルスルフィニル基、エチルスルフィニル基、ｎ−プロピルスルフィニル基、イソプロピルスルフィニル基、ｎ−ブチルスルフィニル基、イソブチルスルフィニル基、ｓｅｃ−ブチルスルフィニル基、ｔｅｒｔ−ブチルスルフィニル基等の、アルキル部分が炭素数１〜４の直鎖状又は分枝鎖状であるアルキルスルフィニル基を挙げることができる。
【００４４】
Ｃ１−４アルキルスルホニル基としては、例えばメチルスルホニル基、エチルスルホニル基、ｎ−プロピルスルホニル基、イソプロピルスルホニル基、ｎ−ブチルスルホニル基、イソブチルスルホニル基、ｓｅｃ−ブチルスルホニル基、ｔｅｒｔ−ブチルスルホニル基等の、アルキル部分が炭素数１〜４の直鎖状又は分枝鎖状であるアルキルスルホニル基を挙げることができる。
【００４５】
Ｃ１−６の直鎖もしくは分枝鎖状アルキレン基としては、例えばメチレン基、エチレン基、トリメチレン基、２−メチルトリメチレン基、２，２−ジメチルトリメチレン基、１−メチルトリメチレン基、メチルメチレン基、エチルメチレン基、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基等を挙げることができる。
【００４６】
Ｃ２−６の直鎖もしくは分枝鎖状アルケニレン基としては、例えばビニリデン基、プロピレン基、ブテニレン基等を挙げることができる。
【００４７】
Ｃ１−４アルキレン基としては、例えばメチレン基、エチレン基、トリメチレン基、２−メチルトリメチレン基、２，２−ジメチルトリメチレン基、１−メチルトリメチレン基、メチルメチレン基、エチルメチレン基、テトラメチレン基等を挙げることができる。
【００４８】
本発明のシアノメチレン化合物（１）の中でも、ＲがＣ１−２０の直鎖もしくは分枝鎖状アルキル基、Ｃ３−８シクロアルキル基、フェニル基、ベンジル基又はヘテロ環基（フェニル基、ベンジル基及びヘテロ環基上には、ハロゲン原子、Ｃ１−４アルキル基、Ｃ１−４ハロアルキル基、Ｃ１−４アルコキシ基、Ｃ１−４ハロアルコキシ基、Ｃ１−４アルコキシカルボニル基、Ｃ１−４アルキルアミノカルボニル基、Ｃ１−４アルコキシイミノＣ１−４アルキル基、Ｃ１−４アルキルアミノ基、Ｃ１−４アルキルカルボニル基、Ｃ１−４アルキルチオ基、カルバモイル基、フェノキシ基、ベンジルオキシ基、ニトロ基及びシアノ基から選ばれる少なくとも１種の置換基が置換していてもよい。）であり、Ｒ１がＣ１−８の直鎖もしくは分枝鎖状アルキル基、Ｃ３−８シクロアルキル基、フェニル基、ベンジル基又はピリジル基（フェニル基、ベンジル基及びピリジル基上には、ハロゲン原子、Ｃ１−４アルキル基、Ｃ１−４ハロアルキル基、Ｃ１−４アルコキシ基、Ｃ１−４ハロアルコキシ基、Ｃ１−４アルコキシカルボニル基、Ｃ１−４アルキルアミノ基、ジＣ１−４アルキルアミノ基、Ｃ２−４アルケニル基、Ｃ１−４アルキルチオ基、Ｃ１−４アルキルスルフィニル基、Ｃ１−４アルキルスルホニル基、フェニル基、フェノキシ基、ニトロ基及びシアノ基から選ばれる少なくとも１種の置換基が置換していてもよい。）であり、ＡがＣ１−６の直鎖もしくは分枝鎖状アルキレン基、Ｃ２−４の直鎖もしくは分枝鎖状アルケニレン基又は基−ＣＨ２−Ｂ−ＣＨ２−（式中Ｂはフェニレン基を示す）であり、Ｙが硫黄原子、スルフィニル基又はスルホニル基であり、ａが０又は１である化合物が好ましい。
【００４９】
また、本発明のシアノメチレン化合物（１）の中でも、Ｒがフェニル基（フェニル基上には、ハロゲン原子、Ｃ１−４アルキル基、Ｃ１−４ハロアルキル基、Ｃ１−４アルコキシ基、Ｃ１−４ハロアルコキシ基、Ｃ１−４アルキルカルボニル基、Ｃ１−４アルキルチオ基及びシアノ基から選ばれる少なくとも１種の置換基が置換していてもよい。）であり、Ｒ１がフェニル基又はピリジル基（フェニル基及びピリジル基上には、ハロゲン原子、Ｃ１−４アルキル基、Ｃ１−４ハロアルキル基、Ｃ１−４アルコキシ基、Ｃ１−４ハロアルコキシ基、Ｃ１−４アルコキシカルボニル基、Ｃ１−４アルキルアミノ基、ジＣ１−４アルキルアミノ基、Ｃ２−４アルケニル基、Ｃ１−４アルキルチオ基、Ｃ１−４アルキルスルフィニル基、Ｃ１−４アルキルスルホニル基、フェニル基、フェノキシ基、ニトロ基及びシアノ基から選ばれる少なくとも１種の置換基が置換していてもよい。）であり、ＡがＣ１−６の直鎖もしくは分枝鎖状アルキレン基であり、Ｙが硫黄原子であり、ａが０又は１であるシアノメチレン化合物がより好ましい。
【００５０】
本発明のシアノメチレン化合物（１）の中でも、Ａがエチレン基であり、ＹがＳであり、ａが１であり、Ｒ及びＲ１が下記に示されるフェニル基であるシアノメチレン化合物が特に好ましい。
【００５１】
【化４】
【表１】
表１においてＭｅはメチル基、Ｅｔはエチル基を意味する。
【００５４】
本発明のシアノメチレン化合物（１）は、１種単独で又は２種以上混合して使用される。
【００５５】
本発明の殺菌剤組成物は、上記式（１）で表されるシアノメチレン化合物及び特定の農園芸用殺菌活性化合物を含有することを特徴とする。
【００５６】
農園芸用殺菌活性化合物は、ＳＨ阻害活性化合物、アクリル酸系化合物、ベンズイミダゾール系化合物、ジカルボキシイミド系化合物、グアニジン系化合物、酸アミド系化合物、アニリノピリミジン系化合物、モルホリン系化合物、ベンゾイソチアゾール系化合物、カーバメート系化合物、有機リン系化合物、ステロール生合成阻害活性化合物、フェニルピロール系化合物及び呼吸阻害系化合物からなる群から選ばれる少なくとも１種である。
【００５７】
ＳＨ阻害活性化合物としては、例えば、銅化合物、ジネブ、マンネブ、マンゼブ、ジラム、ポリカーバメート、チウラム、臭化メチル、有機砒素、ダゾメット、クロロタロニル、ピリジニトリル、アニラジン、ジクロフルアニド、キャプタン、キャプタフォル、フォルペット、ジクロン、フルオロイミド、ジチアノン、フルアジナム等が挙げられる。
【００５８】
アクリル酸系化合物としては、例えば、アゾキシストロビン、クレソキシムメチル、メトミノストロビン、ピラクロストロビン、トリフロキシストロビン、ピコキシストロビン等が挙げられる。
【００５９】
ベンズイミダゾール系化合物としては、例えば、ベノミル、チオファネートメチル、カルベンダジウム、チアベンダゾール等が挙げられる。
【００６０】
ジカルボキシイミド系化合物としては、例えば、イプロジオン、プロシミドン等が挙げられる。
【００６１】
グアニジン系化合物としては、例えば、イミノクタジン等が挙げられる。
【００６２】
酸アミド系化合物としては、例えば、カルボキシン、メプロニル、フルトラニル、ペンシクロン、フラメトピル、チフルザミド等が挙げられる。
【００６３】
アニリノピリミジン系化合物としては、例えば、シプロジニル、メパニピリム、ピリメタニル等が挙げられる。
【００６４】
モルホリン系化合物としては、例えば、ジメトモルフ、フェンプロピモルフ等が挙げられる。
【００６５】
ベンゾイソチアゾール系化合物としては、例えば、プロベナゾール等が挙げられる。
【００６６】
カーバメート系化合物としては、例えば、ジエトフェンカルブ、ベンチアバリカルブ、イプロバリカルブ等が挙げられる。
【００６７】
有機リン系化合物としては、例えば、ホセチル、ピラゾホス、トリクロホスメチル等が挙げられる。
【００６８】
ステロール生合成阻害活性化合物としては、例えば、ブロムコナゾール、シプロコナゾール、ジフェノコナール、フェンブコナゾール、フルトリアホール、ヘキサコナゾール、プロピコナゾール、テブコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリフルミゾール、ビテルタノール、イミベンコナゾール、ジニコナゾール、フェンプロピモルフ、フェンプロピジン、トリデモルフ、エポキシコナゾール、フルキンコナゾール、プロクロラズ、メトコナゾール等が挙げられる。
【００６９】
フェニルピロール系化合物としては、例えば、フェンピクロニル、フルジオキソニル等が挙げられる。
【００７０】
呼吸阻害系化合物としては、例えば、ファモキサドン、フェナミドン、シアゾファミド等が挙げられる。
【００７１】
これら農園芸用殺菌活性化合物のうちで、ＳＨ阻害活性化合物、アクリル酸系化合物及びステロール生合成阻害活性化合物が好ましい。
【００７２】
本発明殺菌剤組成物における一般式（１）で表されるシアノメチレン化合物と農園芸用殺菌活性化合物との配合割合は、特に制限されないが、一般式（１）で表されるシアノメチレン化合物１重量部に対して、農園芸用殺菌活性化合物を、通常０．０１〜１０００重量部、好ましくは０．０５〜１００重量部、より好ましくは０．１〜５０重量部とするのが好ましい。
【００７３】
本発明殺菌剤組成物は、そのまま殺菌剤として使用することも考えられるが、公知の方法によって、例えば、油剤、乳剤、水和剤、フロアブル剤、粒剤、粉剤、エアゾール剤、煙霧剤等の任意の形態に製剤化することができる。斯かる製剤は、例えば、固体担体、液体担体、ガス状担体等の単体と混合し、必要に応じて界面活性剤、その他の製剤用補助剤を添加して製造することができる。
【００７４】
固体担体としては、例えば、粘土類（カオリンクレー、珪藻土、合成含水酸化珪素、ベントナイト、フバサミクレー、酸性白土等）、タルク類、セラミック、その他の無機鉱物（セライト、石英、硫黄、活性炭、炭酸カルシウム、水和シリカ等）、化学肥料（硫安、燐安、硝安、尿素、塩安等）等の微粉末、粒状物等を挙げることができる。
【００７５】
液体担体としては、例えば、水、アルコール類（メタノール、エタノール等）、ケトン類（アセトン、メチルエチルケトン等）、芳香族炭化水素類（ベンゼン、トルエン、キシレン、エチルベンゼン、メチルナフタレン等）、脂肪族炭化水素類（ヘキサン、シクロヘキサン、灯油、軽油等）、エステル類（酢酸エチル、酢酸ブチル等）、ニトリル類（アセトニトリル、イソブチロニトリル等）、エーテル類（ジイソプロピルエーテル、ジオキサン等）、酸アミド類（Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド等）、ハロゲン化炭化水素類（ジクロロメタン、トリクロロエタン、四塩化炭素等）、ジメチルスルホキシド、大豆油、綿実油等の植物油等を挙げることができる。
【００７６】
ガス状担体（即ち噴射剤）としては、例えば、ブタンガス、ＬＰＧ（液化石油ガス）、ジメチルエーテル、炭酸ガス等を挙げることができる。
【００７７】
界面活性剤としては、例えば、アルキル硫酸エステル類、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキルアリールエーテル類及びそのポリオキシエチレン化物、ポリエチレングリコールエーテル類、多価アルコールエステル類、糖アルコール化合物等を挙げることができる。
【００７８】
製剤補助剤としては、例えば、カゼイン、ゼラチン、多糖類（でんぷん粉、アラビアガム、セルロース化合物、アルギン酸等）、リグニン化合物、ベントナイト、糖類、合成水溶性高分子（ポリビニルアルコール、ポリビニルピロリドン、ポリアクリル酸類等）等の固着剤、ＰＡＰ（酸性リン酸イソプロピル）、ＢＢＨ（２，６−ジ−ｔｅｒｔ−ブチル−４−メトキシフェノール）、ＢＨＡ（２−ｔｅｒｔ−ブチル−４−メトキシフェノールと３−ｔｅｒｔ−ブチル−４−メトキシフェノールとの混合物）、植物油、鉱物油、脂肪酸とそのエステル等の安定剤等を挙げることができる。
【００７９】
これらの製剤中には、一般式（１）で表されるシアノメチレン化合物と農園芸用殺菌活性化合物とが、それら合計量で、通常、０．１〜９９．９重量％、好ましくは、０．５〜８０重量％含有されている。
【００８０】
製剤化された本発明の殺菌剤組成物は、そのまま使用してもよく、又は水等の溶剤で希釈して用いてもよい。また、他の殺虫剤、殺線虫剤、殺ダニ剤、殺菌剤、除草剤、植物生長調節剤、共力剤、土壌改良剤等の各種製剤と予め混合して製剤化しておいてもよい。或いは、本発明の殺菌剤組成物又はその製剤と上記各種製剤とを使用の際に同時に用いてもよい。
【００８１】
本発明殺菌剤組成物の施用量は特に制限されないが、有効成分濃度、製剤形態、対象病害及び作物の種類、病害の程度、施用時期、施用方法、併用する薬剤（殺虫剤、殺線虫剤、殺ダニ剤、殺菌剤、除草剤、植物生長調節剤、共力剤、土壌改良剤等）及び肥料の使用量又は種類等の種々の条件に応じて広い範囲から適宜選択できるが、通常１００００ｍ２当たり、有効成分合計量にして１〜１０００ｇ、好ましくは１０〜１００ｇとすればよい。
【００８２】
乳剤、水和剤、フロアブル剤等を水で希釈して施用する場合、その施用濃度は１〜１０００ｐｐｍ、好ましくは１０〜２５０ｐｐｍとすればよく、粒剤、粉剤等は、通常希釈することなくそのまま施用する。
【００８３】
本発明の殺菌剤組成物は、広範囲な農業上の病害菌の防除に利用でき、特にオオムギ、コムギ、キュウリ、イチゴ、ナス、ブドウ等のうどんこ病に対して、卓効を示す。
【００８４】
【発明の効果】
本発明殺菌剤組成物は、一般式（１）で表されるシアノメチレン化合物の殺菌活性を向上させることができ、その結果該化合物の使用量を低減することができる。
【００８５】
本発明殺菌剤組成物は、農園芸上の広範囲に亘る病害菌に対して有効なスペクトルを発揮し、該病害菌の防除に利用され得る。
【００８６】
一般式（１）で表されるシアノメチレン化合物と農園芸用殺菌活性化合物とを併用することにより、相乗的な殺菌活性を発現することができる。
【００８７】
【実施例】
以下に、製剤例及び試験例を挙げ、本発明を更に詳しく説明する。
【００８８】
製剤例１
下記表２に示す各成分を混合し、本発明殺菌剤組成物のフロアブル製剤（製剤１〜３）を作製した。また、下記表３に示す各成分を混合して比較用フロアブル製剤（比較製剤１〜４）を作製した。
【００８９】
【表２】
【表３】
表２及び表３において使用されるシアノメチレン化合物Ａは、前記表１中のＮｏ．１の化合物である。また、クロロタロニルはＳＨ阻害活性化合物、アゾキシストロビンはアクリル酸系化合物、ヘキサコナゾールはステロール生合成阻害活性化合物である。
【００９２】
試験例（キュウリうどんこ病に対する効果試験）
第１葉を形成したキュウリ苗に前記製剤例で調整した各フロアブル製剤を所定濃度に希釈し散布した。風乾後、分生胞子懸濁液を噴霧接種した。温室内に置き、１０日後に第１葉の発病程度を調査した。有効度（％）を以下の式より算出した。
【００９３】
有効度（％）＝［１−（処理区の発病程度／無処理区の発病程度）］×１００
また、本発明の殺菌剤組成物の期待される有効度（Ｅ）をゴルビーの式（Ｗｅｅｄ，１５，２０−２２（１９６６））から算出して計算上の有効度（％）とし、実際の有効度と比較した。
【００９４】
Ｅ＝ｘ＋ｙ−（ｘ・ｙ／１００）
数式中、Ｅは一般式（１）で表されるシアノメチレン化合物及び該化合物と併用する殺菌活性化合物をそれぞれの濃度ｐ及びｑで使用した場合に期待される有効度を％で示したものである。ｘは一般式（１）で表されるシアノメチレン化合物を濃度ｐで使用した時の有効度を示し、ｙは併用する殺菌活性化合物を濃度ｑで使用した時の有効度を示したものである。
【００９５】
結果を表４に示す。
【００９６】
【表４】
表４から明らかなように、本発明の殺菌剤組成物を利用することにより、各有効成分をそれぞれ単独で使用した場合に比べ、相乗効果により高い殺菌効果を得ることができる。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to an agricultural and horticultural fungicide composition.
[0002]
[Prior art]
General formula (1)
[0003]
Embedded image
[Wherein R is C1-20A linear or branched alkyl group of3-8Cycloalkyl group, aryl group, aryl C1-4It represents an alkyl group or a heterocyclic group. Aryl group, aryl C1-4On the alkyl group and the heterocyclic group, a halogen atom, C1-4Alkyl group, C1-4Haloalkyl group, C1-4Alkoxy group, C1-4Haloalkoxy group, C1 -4Alkoxycarbonyl group, C1-4Alkylaminocarbonyl group, C1-4Alkoxy imino C1-4Alkyl group, C1-4Alkylamino group, C1-4Alkylcarbonyl group, C1-4Alkylthio group, aryl C1-4At least one substituent selected from an alkyl group, a carbamoyl group, a phenoxy group, a benzyloxy group, a nitro group and a cyano group may be substituted.
[0005]
R1Is C1-8A linear or branched alkyl group of3-8Cycloalkyl group, aryl group, aryl C1-4It represents an alkyl group or a heterocyclic group. Aryl group, aryl C1-4On the alkyl group and the heterocyclic group, a halogen atom, C1-4Alkyl group, C1-4Haloalkyl group, C1-4Alkoxy group, C1-4Haloalkoxy group, C1-4Alkoxycarbonyl group, C1-4Alkylamino group, di C1-4Alkylamino group, C2-4Alkenyl group, C1-4Alkylthio group, C1-4Alkylsulfinyl group, C1-4At least one substituent selected from an alkylsulfonyl group, a phenyl group, a phenoxy group, a nitro group and a cyano group may be substituted.
[0006]
A is C1-6A linear or branched alkylene group, C2-6A linear or branched alkenylene group of the formula2-B-CH2-(B represents a phenylene group), a group -CH2-OB-CH2-(B is as defined above) or a group -Z-CO- (Z is C1-4An alkylene group).
[0007]
Y represents a sulfur atom, a sulfinyl group or a sulfonyl group.
[0008]
a represents 0 or 1. ]
Is known as a compound having bactericidal activity (Patent Document 1).
[0009]
Compounds having a fungicidal activity for agricultural and horticultural use include SH inhibitory active compounds, acrylic acid compounds, benzimidazole compounds, dicarboximide compounds, guanidine compounds, acid amide compounds, anilinopyrimidine compounds, and morpholine compounds. Many compounds such as compounds, benzoisothiazole compounds, carbamate compounds, organophosphorus compounds, sterol biosynthesis inhibiting active compounds, phenylpyrrole compounds, respiratory inhibition compounds and the like have been developed and used (Non-patent Documents). 1 to Non-Patent Document 4).
[0010]
To date, it has not been specifically known to combine the cyanomethylene compound represented by the above general formula (1) with these compounds having an agricultural and horticultural fungicidal activity.
[0011]
By the way, crops are exposed to a variety of diseases and pests. Therefore, in general, in order to compensate for the lack in the bactericidal activity ability of the fungicidally active compound and to improve the level of the ability, a pesticide formulation is developed by mixing with other fungicidally active compounds. It has been attempted to.
[0012]
However, even if different fungicidally active compounds are mixed, in most cases, depending on the combination, the fungicidal activity originally possessed is impaired or only an additive effect is given.
[0013]
[Patent Document 1]
WO 01/47902, Claims
[0014]
[Non-patent document 1]
Pestic. Sci. ,31, 499-519 (1991).
[0015]
[Non-patent document 2]
Brighton Crop Prot. Conf. -Pests and Diseases, 501-508 (1994).
[0016]
[Non-Patent Document 3]
Brighton Crop Prot. Conf. -Pests and Diseases, 65-72 (1988).
[0017]
[Non-patent document 4]
Brighton Crop Prot. Conf. -Pests and Diseases, 17-23 (1988)
[0018]
[Problems to be solved by the invention]
The present invention provides a fungicide composition that improves the bactericidal activity of the cyanomethylene compound represented by the general formula (1), reduces the amount of the compound used, and is effective against a wide range of pathogenic bacteria in agriculture and horticulture. The task is to
[0019]
[Means for Solving the Problems]
The present inventor has conducted intensive studies to solve the above-mentioned problems, and as a result, by combining the cyanomethylene compound represented by the general formula (1) with a specific agricultural / horticultural fungicidal active compound shown below, the present invention Has been found to be able to solve the above problems. The present invention has been completed based on such findings.
[0020]
That is, the present invention provides (1) a general formula (1)
[0021]
Embedded image
[Wherein, R, R1, A, Y and a are the same as above. ]
And (2) SH-inhibiting compounds, acrylic acid compounds, benzimidazole compounds, dicarboxyimide compounds, guanidine compounds, acid amide compounds, anilinopyrimidine compounds, and morpholine compounds A compound, a benzoisothiazole-based compound, a carbamate-based compound, an organic phosphorus-based compound, a sterol biosynthesis-inhibiting active compound, a phenylpyrrole-based compound, and at least one fungicidal active compound for agricultural and horticultural use selected from the group consisting of respiratory inhibiting compounds. It relates to a fungicide composition for agricultural and horticultural use as an active ingredient.
[0023]
BEST MODE FOR CARRYING OUT THE INVENTION
In the general formula (1), R, R1Specific examples of the groups represented by A, Z and Z include the following.
[0024]
C1-20Examples of the linear or branched alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and n-pentyl groups. , N-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group , N-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group and the like.
[0025]
C3-8Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
[0026]
Examples of the aryl group include a phenyl group and a naphthyl group.
[0027]
Aryl C1-4Examples of the alkyl group include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylpropyl group, a 2-phenylpropyl group, and a 3-phenylpropyl group.
[0028]
Examples of the heterocyclic group include a pyridyl group, a pyrimidyl group, a benzotriazolyl group, a 1,2,4-triazol-1-yl group, a 2-thienyl group, a pyrazinyl group, a pyridazinyl group, a 2-benzothiazolyl group, and an oxazolyl group. , Isoxazolyl group, thiazolyl group, 8-quinolyl group, oxadiazolyl group and the like.
[0029]
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
[0030]
C1-4Examples of the alkyl group include a linear or branched alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group. A chain alkyl group can be mentioned.
[0031]
C1-4Examples of the haloalkyl group include a fluoromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 1-fluoroethyl group, a pentafluoroethyl group, Substituted with 1 to 9 halogen atoms such as fluoropropyl group, 2-chloropropyl group, 3-fluoropropyl group, 3-chloropropyl group, 1-fluorobutyl group, 1-chlorobutyl group, and 4-fluorobutyl group. And straight-chain or branched alkyl groups.
[0032]
C1-4Examples of the alkoxy group include linear groups having 1 to 4 carbon atoms such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, and tert-butoxy. Or a branched alkoxy group.
[0033]
C1-4Examples of the haloalkoxy group include a fluoromethoxy group, a chloromethoxy group, a bromomethoxy group, an iodomethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, and a 1-fluoroethoxy group. , 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, 1-fluoropropoxy group, 2-chloropropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 1-fluorobutoxy group, 1-chloro Examples thereof include a linear or branched alkoxy group having 1 to 4 carbon atoms and substituted with 1 to 9 halogen atoms such as a butoxy group and a 4-fluorobutoxy group.
[0034]
C1-4Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group, an n-butoxycarbonyl group, an isobutoxycarbonyl group, a sec-butoxycarbonyl group, a tert-butoxycarbonyl group, and the like. In which the alkoxy moiety is a straight-chain or branched-chain alkoxycarbonyl group having 1 to 4 carbon atoms.
[0035]
C1-4Examples of the alkylaminocarbonyl group include a methylaminocarbonyl group, an ethylaminocarbonyl group, an n-propylaminocarbonyl group, an isopropylaminocarbonyl group, an n-butylaminocarbonyl group, an isobutylaminocarbonyl group, a sec-butylaminocarbonyl group, and tert. Examples thereof include a straight-chain or branched-chain alkylaminocarbonyl group having 1 to 4 carbon atoms, such as a -butylaminocarbonyl group.
[0036]
C1-4Alkoxy imino C1-4Examples of the alkyl group include a methoxyiminomethyl group, an ethoxyiminomethyl group, a 1- (n-propoxyimino) ethyl group, an isopropoxyiminomethyl group, a 2- (n-butoxyimino) ethyl group, and a sec-butoxyiminomethyl group. Wherein the alkoxy moiety such as a tert-butoxyiminomethyl group is linear or branched having 1 to 4 carbon atoms, and the alkyl moiety is linear or branched having 1 to 4 carbon atoms. Alkyl groups can be mentioned.
[0037]
C1-4Examples of the alkylamino group include an alkyl moiety such as a methylamino group, an ethylamino group, an n-propylamino group, an isopropylamino group, an n-butylamino group, an isobutylamino group, a sec-butylamino group, and a tert-butylamino group. Is a linear or branched alkylamino group having 1 to 4 carbon atoms.
[0038]
C1-4Examples of the alkylcarbonyl group include alkyl such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, and tert-butylcarbonyl. Examples thereof include a linear or branched alkylcarbonyl group having 1 to 4 carbon atoms.
[0039]
C1-8Examples of the linear or branched alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and n-pentyl groups. , N-hexyl group, n-heptyl group, n-octyl group and the like.
[0040]
Di C1-4Examples of the alkylamino group include dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, diisobutylamino, sec-butylamino, and di-tert-butylamino. Examples thereof include a linear or branched dialkylamino group having an alkyl portion such as a group having 1 to 4 carbon atoms.
[0041]
C2-4Examples of the alkenyl group include a vinyl group, an allyl group, an isopropenyl group, a 2-butenyl group, a 3-butenyl group, and a 1-methyl-2-propenyl group.
[0042]
C1-4Examples of the alkylthio group include an alkyl moiety having 1 to 4 carbon atoms such as a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a sec-butylthio group, and a tert-butylthio group. And a linear or branched alkylthio group.
[0043]
C1-4Examples of the alkylsulfinyl group include alkylsulfinyl, methylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, and tert-butylsulfinyl. Examples thereof include a linear or branched alkylsulfinyl group having 1 to 4 carbon atoms.
[0044]
C1-4Examples of the alkylsulfonyl group include alkyls such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, and tert-butylsulfonyl. Examples thereof include a linear or branched alkylsulfonyl group having 1 to 4 carbon atoms.
[0045]
C1-6Examples of the linear or branched alkylene group include a methylene group, an ethylene group, a trimethylene group, a 2-methyltrimethylene group, a 2,2-dimethyltrimethylene group, a 1-methyltrimethylene group, a methylmethylene group, Examples thereof include an ethylmethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group.
[0046]
C2-6Examples of the linear or branched alkenylene group include a vinylidene group, a propylene group and a butenylene group.
[0047]
C1-4Examples of the alkylene group include methylene, ethylene, trimethylene, 2-methyltrimethylene, 2,2-dimethyltrimethylene, 1-methyltrimethylene, methylmethylene, ethylmethylene, and tetramethylene. Can be mentioned.
[0048]
In the cyanomethylene compound (1) of the present invention, R is C1-20A linear or branched alkyl group of3-8A cycloalkyl group, a phenyl group, a benzyl group or a heterocyclic group (a halogen atom, C1-4Alkyl group, C1-4Haloalkyl group, C1-4Alkoxy group, C1-4Haloalkoxy group, C1-4Alkoxycarbonyl group, C1-4Alkylaminocarbonyl group, C1-4Alkoxy imino C1-4Alkyl group, C1-4Alkylamino group, C1-4Alkylcarbonyl group, C1-4At least one substituent selected from an alkylthio group, a carbamoyl group, a phenoxy group, a benzyloxy group, a nitro group and a cyano group may be substituted. ) And R1Is C1-8A linear or branched alkyl group of3-8A cycloalkyl group, a phenyl group, a benzyl group, or a pyridyl group (a halogen atom, C1-4Alkyl group, C1-4Haloalkyl group, C1-4Alkoxy group, C1-4Haloalkoxy group, C1-4Alkoxycarbonyl group, C1-4Alkylamino group, di C1-4Alkylamino group, C2-4Alkenyl group, C1-4Alkylthio group, C1-4Alkylsulfinyl group, C1-4At least one substituent selected from an alkylsulfonyl group, a phenyl group, a phenoxy group, a nitro group and a cyano group may be substituted. ) And A is C1-6A linear or branched alkylene group, C2-4Linear or branched alkenylene group or group -CH2-B-CH2(Wherein B represents a phenylene group), Y is a sulfur atom, a sulfinyl group or a sulfonyl group, and a compound in which a is 0 or 1 is preferable.
[0049]
In the cyanomethylene compound (1) of the present invention, R represents a phenyl group (a halogen atom, C1-4Alkyl group, C1-4Haloalkyl group, C1-4Alkoxy group, C1-4Haloalkoxy group, C1-4Alkylcarbonyl group, C1-4At least one substituent selected from an alkylthio group and a cyano group may be substituted. ) And R1Is a phenyl group or a pyridyl group (a halogen atom, C1-4Alkyl group, C1-4Haloalkyl group, C1-4Alkoxy group, C1-4Haloalkoxy group, C1-4Alkoxycarbonyl group, C1-4Alkylamino group, di C1-4Alkylamino group, C2-4Alkenyl group, C1-4Alkylthio group, C1-4Alkylsulfinyl group, C1-4At least one substituent selected from an alkylsulfonyl group, a phenyl group, a phenoxy group, a nitro group and a cyano group may be substituted. ) And A is C1-6Is more preferably a cyanomethylene compound wherein Y is a sulfur atom and a is 0 or 1.
[0050]
In the cyanomethylene compound (1) of the present invention, A is an ethylene group, Y is S, a is 1, R and R1Is particularly preferably a cyanomethylene compound represented by the following phenyl group.
[0051]
Embedded image
[Table 1]
In Table 1, Me represents a methyl group and Et represents an ethyl group.
[0054]
The cyanomethylene compound (1) of the present invention is used alone or as a mixture of two or more.
[0055]
The fungicide composition of the present invention is characterized by containing the cyanomethylene compound represented by the above formula (1) and a specific agricultural / horticultural fungicidal active compound.
[0056]
Agricultural and horticultural bactericidal active compounds include SH inhibitory active compounds, acrylic acid compounds, benzimidazole compounds, dicarboximide compounds, guanidine compounds, acid amide compounds, anilinopyrimidine compounds, morpholine compounds, benzoisomers. It is at least one selected from the group consisting of thiazole compounds, carbamate compounds, organophosphorus compounds, sterol biosynthesis inhibitory compounds, phenylpyrrole compounds and respiratory inhibitors.
[0057]
Examples of SH-inhibiting compounds include copper compounds, zineb, maneb, manzeb, ziram, polycarbamate, thiuram, methyl bromide, organic arsenic, dazomet, chlorothalonil, pyridinitrile, anilazine, diclofluanid, captan, captafor, folpet , Dicron, fluoroimide, dithianon, fluazinam and the like.
[0058]
Examples of the acrylic acid compound include azoxystrobin, kresoximmethyl, methinostrobin, pyraclostrobin, trifloxystrobin, picoxystrobin and the like.
[0059]
Examples of the benzimidazole-based compound include benomyl, thiophanate methyl, carbendazim, and thiabendazole.
[0060]
Examples of the dicarboximide compound include iprodione, procymidone, and the like.
[0061]
Examples of the guanidine-based compound include iminoctadine.
[0062]
Examples of the acid amide-based compound include carboxin, mepronil, flutranyl, pencyclon, flametopyr, thifluzamide and the like.
[0063]
Examples of the anilinopyrimidine-based compound include cyprodinil, mepanipyrim, pyrimethanil and the like.
[0064]
Examples of the morpholine-based compound include dimethomorph and fenpropimorph.
[0065]
Examples of the benzoisothiazole-based compound include probenazole.
[0066]
Examples of the carbamate-based compound include dietofencarb, benciavaricarb, iprovalicarb and the like.
[0067]
Examples of the organic phosphorus compound include fosetyl, pyrazophos, trichofosmethyl, and the like.
[0068]
Examples of the sterol biosynthesis-inhibiting compounds include, for example, bromconazole, cyproconazole, difenoconal, fenbuconazole, flutriahole, hexaconazole, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, trifmenol Examples include lumizole, bitertanol, imibenconazole, diniconazole, fenpropimorph, fenpropidine, tridemorph, epoxyconazole, fluquinconazole, prochloraz, metconazole, and the like.
[0069]
Examples of the phenylpyrrole-based compound include fenpiclonil, fludioxonil, and the like.
[0070]
Examples of respiratory inhibition compounds include famoxadone, phenamidone, cyazofamid and the like.
[0071]
Among these germicidal active compounds for agricultural and horticultural use, SH inhibitory active compounds, acrylic acid compounds and sterol biosynthesis inhibitory active compounds are preferred.
[0072]
The mixing ratio of the cyanomethylene compound represented by the general formula (1) and the fungicidal active compound for agricultural and horticultural use in the fungicide composition of the present invention is not particularly limited, but the cyanomethylene compound 1 represented by the general formula (1) is not limited. The amount of the fungicidally active compound for agricultural and horticultural use is usually 0.01 to 1000 parts by weight, preferably 0.05 to 100 parts by weight, more preferably 0.1 to 50 parts by weight, based on parts by weight.
[0073]
The bactericide composition of the present invention may be used as a bactericide as it is, but by a known method, for example, oils, emulsions, wettable powders, flowables, granules, powders, aerosols, aerosols, etc. It can be formulated in any form. Such a preparation can be produced by, for example, mixing with a simple substance such as a solid carrier, a liquid carrier, and a gaseous carrier, and adding a surfactant and other formulation auxiliaries as necessary.
[0074]
As the solid carrier, for example, clays (kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (celite, quartz, sulfur, activated carbon, calcium carbonate, Hydrated silica), fine powders such as chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, salt ammonium, etc.), and granular materials.
[0075]
Examples of the liquid carrier include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (Hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N , N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, vegetable oils such as soybean oil, cottonseed oil and the like.
[0076]
Examples of the gaseous carrier (ie, propellant) include butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas, and the like.
[0077]
Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol compounds and the like. Can be mentioned.
[0078]
As formulation aids, for example, casein, gelatin, polysaccharides (starch, gum arabic, cellulose compounds, alginic acid, etc.), lignin compounds, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids) Fixing agents such as PAP (acidic isopropyl phosphate), BBH (2,6-di-tert-butyl-4-methoxyphenol), and BHA (2-tert-butyl-4-methoxyphenol and 3-tert-). Butyl-4-methoxyphenol), vegetable oils, mineral oils, stabilizers such as fatty acids and their esters, and the like.
[0079]
In these preparations, the cyanomethylene compound represented by the general formula (1) and the fungicidally active compound for agricultural and horticultural use are usually 0.1 to 99.9% by weight, preferably 0 to 9% by weight in total thereof. 0.5-80% by weight.
[0080]
The formulated bactericide composition of the present invention may be used as it is, or may be used after being diluted with a solvent such as water. In addition, other insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, may be pre-mixed and formulated with various preparations such as soil improvers. . Alternatively, the fungicidal composition of the present invention or the preparation thereof and the above-mentioned various preparations may be used at the same time.
[0081]
The application rate of the fungicide composition of the present invention is not particularly limited, but the concentration of the active ingredient, the form of the preparation, the type of the target disease and crop, the degree of the disease, the application time, the application method, and the concomitant drug (pesticide, nematicide) , Acaricide, fungicide, herbicide, plant growth regulator, synergist, soil conditioner, etc.) and fertilizer can be appropriately selected from a wide range according to various conditions such as the amount or type of fertilizer.2The total amount of the active ingredient may be 1 to 1000 g, preferably 10 to 100 g.
[0082]
When the emulsion, wettable powder, flowable and the like are diluted with water and applied, the application concentration may be 1 to 1000 ppm, preferably 10 to 250 ppm, and granules, powders and the like are usually used without dilution. Apply.
[0083]
The fungicidal composition of the present invention can be used for controlling a wide range of agriculturally harmful fungi, and is particularly effective against powdery mildew such as barley, wheat, cucumber, strawberry, eggplant, and grape.
[0084]
【The invention's effect】
The fungicide composition of the present invention can improve the fungicidal activity of the cyanomethylene compound represented by the general formula (1), and as a result, the amount of the compound used can be reduced.
[0085]
INDUSTRIAL APPLICABILITY The fungicide composition of the present invention exhibits an effective spectrum against a wide variety of pathogenic fungi on agricultural and horticultural purposes, and can be used for controlling the pathogenic fungi.
[0086]
By using the cyanomethylene compound represented by the general formula (1) in combination with the fungicidal active compound for agricultural and horticultural use, a synergistic fungicidal activity can be exhibited.
[0087]
【Example】
Hereinafter, the present invention will be described in more detail by way of formulation examples and test examples.
[0088]
Formulation Example 1
The components shown in Table 2 below were mixed to prepare flowable formulations (formulations 1 to 3) of the fungicidal composition of the present invention. In addition, each component shown in Table 3 below was mixed to prepare a flowable preparation for comparison (Comparative Preparations 1 to 4).
[0089]
[Table 2]
[Table 3]
The cyanomethylene compound A used in Tables 2 and 3 is No. 1 in Table 1 described above. 1 compound. In addition, chlorothalonil is an SH inhibitory active compound, azoxystrobin is an acrylic acid compound, and hexaconazole is a sterol biosynthesis inhibitory active compound.
[0092]
Test example (effect test for cucumber powdery mildew)
Each flowable preparation prepared in the above preparation example was diluted to a predetermined concentration and sprayed on the cucumber seedlings having formed the first leaves. After air drying, the conidia spore suspension was inoculated by spraying. It was placed in a greenhouse, and after 10 days, the degree of onset of the first leaf was investigated. Effectiveness (%) was calculated from the following equation.
[0093]
Effectiveness (%) = [1- (degree of onset in treated area / degree of onset in untreated area)] × 100
In addition, the expected effectiveness (E) of the fungicide composition of the present invention was determined by the formula of Gorby (Weed,Fifteen, 20-22 (1966)), the calculated effectiveness (%), and comparison with the actual effectiveness.
[0094]
E = x + y- (x · y / 100)
In the formulas, E represents the percent effectiveness expected when the cyanomethylene compound represented by the general formula (1) and the fungicidally active compound used in combination with the compound are used at the respective concentrations p and q. is there. x indicates the effectiveness when the cyanomethylene compound represented by the general formula (1) is used at the concentration p, and y indicates the effectiveness when the concomitant bactericidal active compound is used at the concentration q. .
[0095]
Table 4 shows the results.
[0096]
[Table 4]
As is clear from Table 4, the use of the germicidal composition of the present invention makes it possible to obtain a higher bactericidal effect due to a synergistic effect as compared with the case where each active ingredient is used alone.
Claims (1)
Ｒ１はＣ１−８の直鎖もしくは分枝鎖状アルキル基、Ｃ３−８シクロアルキル基、アリール基、アリールＣ１−４アルキル基又はヘテロ環基を示す。アリール基、アリールＣ１−４アルキル基及びヘテロ環基上には、ハロゲン原子、Ｃ１−４アルキル基、Ｃ１−４ハロアルキル基、Ｃ１−４アルコキシ基、Ｃ１−４ハロアルコキシ基、Ｃ１−４アルコキシカルボニル基、Ｃ１−４アルキルアミノ基、ジＣ１−４アルキルアミノ基、Ｃ２−４アルケニル基、Ｃ１−４アルキルチオ基、Ｃ１−４アルキルスルフィニル基、Ｃ１−４アルキルスルホニル基、フェニル基、フェノキシ基、ニトロ基及びシアノ基から選ばれる少なくとも１種の置換基が置換していてもよい。
ＡはＣ１−６の直鎖もしくは分枝鎖状アルキレン基、Ｃ２−６の直鎖もしくは分枝鎖状アルケニレン基、基−ＣＨ２−Ｂ−ＣＨ２−（Ｂはフェニレン基を示す）、基−ＣＨ２−Ｏ−Ｂ−ＣＨ２−（Ｂは前記に同じ）又は基−Ｚ−ＣＯ−（ＺはＣ１−４アルキレン基を示す）を示す。
Ｙは硫黄原子、スルフィニル基又はスルホニル基を示す。
ａは０又は１を示す。〕
で表されるシアノメチレン化合物、並びに
（２） ＳＨ阻害活性化合物、アクリル酸系化合物、ベンズイミダゾール系化合物、ジカルボキシイミド系化合物、グアニジン系化合物、酸アミド系化合物、アニリノピリミジン系化合物、モルホリン系化合物、ベンゾイソチアゾール系化合物、カーバメート系化合物、有機リン系化合物、ステロール生合成阻害活性化合物、フェニルピロール系化合物及び呼吸阻害系化合物からなる群から選ばれる少なくとも１種の農園芸用殺菌活性化合物
を有効成分とする農園芸用殺菌剤組成物。(1) General formula
R 1 represents a C 1-8 linear or branched alkyl group, a C 3-8 cycloalkyl group, an aryl group, an aryl C 1-4 alkyl group or a heterocyclic group. A halogen atom, a C 1-4 alkyl group, a C 1-4 haloalkyl group, a C 1-4 alkoxy group, a C 1-4 haloalkoxy group on the aryl group, the aryl C 1-4 alkyl group and the heterocyclic group; C 1-4 alkoxycarbonyl group, C 1-4 alkylamino group, diC 1-4 alkylamino group, C 2-4 alkenyl group, C 1-4 alkylthio group, C 1-4 alkylsulfinyl group, C 1- At least one substituent selected from a 4- alkylsulfonyl group, a phenyl group, a phenoxy group, a nitro group and a cyano group may be substituted.
A represents a C 1-6 linear or branched alkylene group, a C 2-6 linear or branched alkenylene group, a group —CH 2 —B—CH 2 — (B represents a phenylene group) , group -CH 2 -O-B-CH 2 - shows the (B have the same meanings) (showing the Z is C 1-4 alkylene group) or a group -Z-CO-.
Y represents a sulfur atom, a sulfinyl group or a sulfonyl group.
a represents 0 or 1. ]
And (2) SH-inhibiting compounds, acrylic acid compounds, benzimidazole compounds, dicarboxyimide compounds, guanidine compounds, acid amide compounds, anilinopyrimidine compounds, and morpholine compounds A compound, a benzoisothiazole-based compound, a carbamate-based compound, an organic phosphorus-based compound, a sterol biosynthesis-inhibiting active compound, a phenylpyrrole-based compound, and at least one fungicidal active compound for agricultural and horticultural use selected from the group consisting of respiration-inhibiting compounds. A fungicide composition for agricultural and horticultural use as an active ingredient.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002327898A JP2004161646A (en) | 2002-11-12 | 2002-11-12 | Fungicide composition for agriculture and horticulture |
| PCT/JP2003/014346 WO2004043149A1 (en) | 2002-11-12 | 2003-11-12 | Bactericide composition for agricultural or horticultural use and method of enhancing bactericidal activity of agricultural or horticultural bactericide |
| AU2003280729A AU2003280729A1 (en) | 2002-11-12 | 2003-11-12 | Bactericide composition for agricultural or horticultural use and method of enhancing bactericidal activity of agricultural or horticultural bactericide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002327898A JP2004161646A (en) | 2002-11-12 | 2002-11-12 | Fungicide composition for agriculture and horticulture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2004161646A true JP2004161646A (en) | 2004-06-10 |
Family
ID=32310530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002327898A Pending JP2004161646A (en) | 2002-11-12 | 2002-11-12 | Fungicide composition for agriculture and horticulture |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2004161646A (en) |
| AU (1) | AU2003280729A1 (en) |
| WO (1) | WO2004043149A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007112760A (en) * | 2005-10-21 | 2007-05-10 | Meiji Seika Kaisha Ltd | Bactericidal mixed composition for agriculture and horticulture |
| EP2084966A1 (en) * | 2005-09-29 | 2009-08-05 | Syngenta Participations AG | Fungicidal compositions |
| WO2010029030A3 (en) * | 2008-09-12 | 2011-04-07 | Basf Se | Fungicidal mixtures |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2012216761B2 (en) * | 2005-09-29 | 2013-10-24 | Syngenta Participations Ag | Fungicidal compositions |
| CN106614629A (en) * | 2016-12-20 | 2017-05-10 | 东莞市瑞德丰生物科技有限公司 | Sterilization composition including flutianil |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6710062B1 (en) * | 1999-12-24 | 2004-03-23 | Otsuka Chemical Co., Ltd. | Cyanomethylene compounds, process for producing the same, and agricultural or horticultural bactericide |
-
2002
- 2002-11-12 JP JP2002327898A patent/JP2004161646A/en active Pending
-
2003
- 2003-11-12 WO PCT/JP2003/014346 patent/WO2004043149A1/en active Application Filing
- 2003-11-12 AU AU2003280729A patent/AU2003280729A1/en not_active Abandoned
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2084966A1 (en) * | 2005-09-29 | 2009-08-05 | Syngenta Participations AG | Fungicidal compositions |
| JP2007112760A (en) * | 2005-10-21 | 2007-05-10 | Meiji Seika Kaisha Ltd | Bactericidal mixed composition for agriculture and horticulture |
| WO2010029030A3 (en) * | 2008-09-12 | 2011-04-07 | Basf Se | Fungicidal mixtures |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004043149A1 (en) | 2004-05-27 |
| AU2003280729A1 (en) | 2004-06-03 |
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