JPS6348842B2 - - Google Patents
Info
- Publication number
- JPS6348842B2 JPS6348842B2 JP6615279A JP6615279A JPS6348842B2 JP S6348842 B2 JPS6348842 B2 JP S6348842B2 JP 6615279 A JP6615279 A JP 6615279A JP 6615279 A JP6615279 A JP 6615279A JP S6348842 B2 JPS6348842 B2 JP S6348842B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- present
- compounds
- compound
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 29
- -1 thiourea compound Chemical class 0.000 claims description 27
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 20
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 claims description 14
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 230000000855 fungicidal effect Effects 0.000 claims description 9
- 239000000417 fungicide Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 27
- 239000000843 powder Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 230000012010 growth Effects 0.000 description 11
- 244000000003 plant pathogen Species 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 241000209094 Oryza Species 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000005909 Kieselgur Substances 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
- 239000000443 aerosol Substances 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000002734 clay mineral Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 230000000391 smoking effect Effects 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
- 150000003585 thioureas Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HPAWGVVEOFUXDF-UHFFFAOYSA-N 1-[(4-bromophenyl)methyl]-3-phenyl-1-propan-2-ylurea Chemical compound C=1C=CC=CC=1NC(=O)N(C(C)C)CC1=CC=C(Br)C=C1 HPAWGVVEOFUXDF-UHFFFAOYSA-N 0.000 description 1
- JZHJUJUXJZHXQE-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-phenyl-1-propan-2-ylurea Chemical compound C=1C=CC=CC=1NC(=O)N(C(C)C)CC1=CC=C(Cl)C=C1 JZHJUJUXJZHXQE-UHFFFAOYSA-N 0.000 description 1
- KKFUQXLXZDEPBM-UHFFFAOYSA-N 1-butan-2-yl-1-[(4-chlorophenyl)methyl]-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)N(C(C)CC)CC1=CC=C(Cl)C=C1 KKFUQXLXZDEPBM-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- VZWFGOMGEWMZMH-UHFFFAOYSA-N 3-(3-methylphenyl)propyl carbamate Chemical compound CC1=CC=CC(CCCOC(N)=O)=C1 VZWFGOMGEWMZMH-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 241000576755 Sclerotia Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241001617088 Thanatephorus sasakii Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 244000000005 bacterial plant pathogen Species 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- VNSBYDPZHCQWNB-UHFFFAOYSA-N calcium;aluminum;dioxido(oxo)silane;sodium;hydrate Chemical compound O.[Na].[Al].[Ca+2].[O-][Si]([O-])=O VNSBYDPZHCQWNB-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 229940071162 caseinate Drugs 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- SHFGJEQAOUMGJM-UHFFFAOYSA-N dialuminum dipotassium disodium dioxosilane iron(3+) oxocalcium oxomagnesium oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Na+].[Na+].[Al+3].[Al+3].[K+].[K+].[Fe+3].[Fe+3].O=[Mg].O=[Ca].O=[Si]=O SHFGJEQAOUMGJM-UHFFFAOYSA-N 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000011419 magnesium lime Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は一般式:
〔式中、
Rは炭素原子数3〜8の分岐アルキル基または
炭素原子数5〜8のシクロアルキル基、
Xはハロゲン原子、ニトロ基、シアノ基または
炭素原子1〜4のアルキル基、
Yは酸素原子またはイオウ原子を示す。〕
で表わされるウレアまたはチオウレア系化合物
と、O―sec―ブチルフエニルメチルカーバメイ
ト、(以下、BPMCと略記する)、m―トリルメ
チルカーバメイト(以下、MTMCと略記する)
のうちの一種、または二種とを、有効成分として
含有することを特徴とする農園芸用殺菌剤に関す
るものである。
本発明者等は新規な農園芸用殺菌剤を開発すべ
く、従来より作用性の異なる薬剤を混合すること
により、その薬剤の効果を協力的且つ相乗的に増
加せしめる作用を有する混合製剤について研究を
重ねてきた。
この度、本発明者等は、極めて優れた殺菌活性
を有し、特に稲紋枯病菌(Pellicularia sasakii)
に対して優れた効果を現わす前記一般式()で
表わされるウレアまたはチオウレア系化合物と、
優れた殺虫効果を現わすBPMC、MTMCのうち
の一種または二種とを、混合した場合、前記一般
式()で表わされるウレアまたはチオウレア系
化合物の殺菌効果が協力的且つ相乗的に増加する
ことを発見した。
本発明の農園芸用殺菌剤を植物病害防除に使用
すると、前記一般式()で表わされるウレアま
たはチオウレア系化合物の濃度が単剤として用い
た場合には的確な防除効果を現わさない範囲にお
いてさえも、この混合により、極めて顕著な協力
作用および相乗作用が働き、その結果、植物病原
菌に対する殺菌能が増大し、的確に防除すること
が認められた。また夫々の単剤自身の効果も同時
に現われるため、殺菌スペクトルの拡大、有害昆
虫類の同時防除が可能となり、農業の省力化、経
済性等の面において、有効であることが確認され
た。
また近年、薬剤抵抗性を獲得した有害昆虫の発
生が大きな問題となつているが、この様な場面に
おいて、有害昆虫と植物病害とを同時に防除する
ためには、前記一般式()の化合物と、m―ト
リルプロピルカーバメイト、O―sec―ブチルフ
エニルプロピルカーバメイト、S―(2―エチル
チオ)エチルジプロピルチオホスフエートのうち
の一種または二種以上とを有効成分として含有す
る混合薬剤を施用することにより、容易に達成す
ることができ、そして混合することにより共働的
相乗効果も現われ、より好都合に利用することが
できる。
前記一般式()で表わされるウレアまたはチ
オウレア系化合物としては具体的には、
N―4―クロルベンジルN―sec―ブチルN′―フ
エニルウレア(またはチオウレア)、
N―4―クロルベンジルN―シクロペンチル
N′―フエニルウレア(またはチオウレア)、
N―4―メチルベンジルN―シクロペンチル
N′―フエニルウレア(またはチオウレア)、
N―4―ニトロベンジルN―シクロペンチル
N′―フエニルウレア(またはチオウレア)、
N―4―シアノベンジルN―シクロペンチル
N′―フエニルウレア(またはチオウレア)、
N―4―クロルベンジルN―イソプロピルN′―
フエニルウレア(またはチオウレア)、
N―4―ブロムベンジルN―イソプロピルN′―
フエニルウレア(またはチオウレア)、
等を挙げることができる。
本発明の農園芸用殺菌剤は、温血動物に対し低
毒性であり、高等植物に対する良好な親和性、即
ち通常の使用濃度では栽培植物に薬害がないとい
う特性があるので、農園芸用薬剤として、病原菌
による植物の病害、および植物病害と有害昆虫の
同時防除に対して全く好都合に使用できる。
本発明の農園芸用殺菌剤を使用する場合、その
まま直接水で希釈して使用するか、または農薬補
助剤を用いて農薬製造分野において一般に行なわ
れている方法により、種々の製剤形態にし使用す
ることができる。これらの種々の製剤は、実際の
使用に際しては、直接そのまま使用するか、また
は水で所望濃度に希釈して使用することができ
る。ここに言う、農薬補助剤は例えば、希釈剤
(溶剤、増量剤、担体)、界面活性剤(可溶化剤、
乳化剤、分散剤、湿展剤)、安定剤、固着剤、エ
ーロゾル用噴射剤、共力剤を挙げることができ
る。
溶剤としては、水:有機溶剤;炭化水素類〔例
えば、n―ヘキサン、石油エーテル、ナフサ、石
油留分(パラフイン蝋、灯油、軽油、中油、重
油)、ベンゼン、トルエン、キシレン類〕、ハロゲ
ン化炭化水素類〔例えば、クロルメチレン、四塩
化炭素、トリクロルエチレン、エチレンクロライ
ド、二臭化エチレン、クロルベンゼンクロロホル
ム〕、アルコール類、〔例えば、メチルアルコー
ル、エチルアルコール、プロピルアルコール、エ
チレングリコール〕、エーテル類、〔例えば、エチ
ルエーテル、エチレンオキシド、ジオキサン〕、
アルコールエーテル類、〔例えばエチレングリコ
ールモノメチルエーテル〕、ケトン類、〔例えば、
アセトン、イソホロン〕、エステル類、〔例えば、
酢酸エチル、酢酸アミル〕、アミド類、〔例えば、
ジメチルホルムアミド、ジメチルアセトアミド〕、
スルホキシド類、〔例えば、ジメチルスルホキシ
ド〕を挙げることができる。
増量剤または担体としては無機質粉粒体;硫
黄、消石灰、マグネシウム石灰、石膏、炭酸カル
シウム、硅石、パーライト、軽石、方解石、珪藻
土、無晶形酸化ケイ素、アルミナ、ゼオライト、
粘土鉱物(例えば、パイロフイライト、滑石、モ
ンモリロナイト、バイデライト、バーミキユライ
ト、カオリナイト、雲母):植物性粉粒体;殻粉、
殿粉、加工デンプン、砂糖、ブドウ糖、植物茎幹
破砕物:合成樹脂粉粒体;フエノール樹脂、尿素
樹脂、塩化ビニル樹脂を挙げることができる。
界面活性剤としては、アニオン(陰イオン)界
面活性剤;アルキル硫酸エステル類、〔例えばラ
ウリル硫酸ナトリウム〕、アリールスルホン酸類、
〔例えばアルキルアリールスルホン酸塩、アルキ
ルナフタレンスルホン酸ナトリウム〕、コハク酸
塩類、ポリエチレングリコールアルキルアリール
エーテル硫酸エステル塩類:カチオン(陽イオ
ン)界面活性剤;アルキルアミン類、〔例えば、
ラウリルアミン、ステアリルトリメチルアンモニ
ウムクロライド、アルキルジメチルベンジルアン
モニウムクロライド〕、ポリオキシエチレンアル
キルアミン類:非イオン界面活性剤;ポリオキシ
エチレングリコールエーテル類、〔例えば、ポリ
オキシエチレンアルキルアリールエーテル、およ
びその縮合物〕ポリオキシエチレングリコールエ
ステル類、〔例えば、ポリオキシエチレン脂肪酸
エステル〕、多価アルコールエステル類、〔例え
ば、ポリオキシエチレンソルビタンモノラウレー
ト〕:両性界面活性剤、等を挙げることができる。
その他、安定剤、固着剤〔例えば、農業用石け
ん、カゼイン石灰、アルギン酸ソーダ、ポリビニ
ルアルコール(PVA)、酢酸ビニル系接着剤、ア
クリル系接着剤〕、エーロゾル用噴射剤〔例えば、
トリクロルフルオルメタン、ジクロルフルオルメ
タン、1,2,2―トリクロル―1,1,2―ト
リフルオルエタン、クロルベンゼン、LNG、低
級エーテル〕:(燻煙剤用)燃焼調節剤〔例えば、
亜硝酸塩、亜鉛末、ジシアンジアミド〕:酸素供
給剤(oxygenyielding)、〔例えば、塩素酸塩、
重クロム酸塩〕:薬害軽減剤〔例えば、硫酸亜鉛、
塩化第一鉄、硝酸銅〕:効力延長剤:分散安定剤
〔例えば、カゼイン、トラガカント、カルボキシ
メチルセルロース(CMC)、ポリビニルアルコー
ル(PVA)〕:共力剤を挙げることができる。
本発明の混合活性化合物は、一般に農薬製造分
野で行われている方法により種々の製剤形態に製
造することができる。
製剤の形態としては、乳剤:油剤:水和剤:水
溶剤:懸濁剤:粉剤:粒剤:粉粒剤:燻煙剤:錠
剤:煙霧剤:糊状剤:カプセル剤等を挙げること
ができる。
本発明の農園芸用殺菌剤は、前記活性成分を
0.1〜95重量%、好ましくは0.5〜90重量%含有す
ることができる。
実際の使用に際しては、前記した種々の製剤お
よび散布用調製物(ready―to―use―
preparation)中の活性化合物含量は、一般に
0.0001〜20重量%、好ましくは0.005〜10重量%
の範囲が適当である。
これら活性成分の含有量は、製剤の形態および
施用する方法、目的、時期、場所および、病原菌
または病原菌および有害昆虫の発生状況等によつ
て適当に変更できる。
本発明の混合活性化合物は、更に必要ならば、
他の農薬、例えば、殺虫剤、殺菌剤、殺ダニ剤、
殺線虫剤、坑ウイルス剤、除草剤、植物生長調整
剤、誘引剤、〔例えば、有機燐酸エステル系化合
物、カーバメート系化合物、ジチオ(またはチオ
ール)カーバメート系化合物、有機塩素系化合
物、ジニトロ系化合物、有機硫黄または金属系化
合物、坑生物質、置換ジフエニルエーテル系化合
物、尿素系化合物、トリアジン系化合物〕また
は/および肥料等を共存させることもできる。
本発明の前記混合活性成分を含有する種々の製
剤または散布用調製物(ready―to―use
prepara―tion)は農薬製造分野にて通常一般に
行われている施用方法、散布、〔例えば液剤散布
(噴霧)、ミステイング(misting)、アトマイズイ
ング(atomizing)、散粉、散粒、水面施用、ポ
アリング(pouring)〕:燻蒸:土壌施用、〔例え
ば、混入、スプリンクリング(sprinkling)、燻
蒸(vaporing)、潅注、〕:表面施用、〔例えば、
塗布、巻付け(banding)、粉衣、被覆〕:浸漬:
毒餌(baiting)等により行うことができる。ま
たいわゆる超高濃度少量散布法(ultra―low―
volume)により使用することもできる。この方
法においては、活性成分を100%含有することが
可能である。
単位面積当りの施用量は、1ヘクタール当り活
性化合物として約0.03〜10Kg、好ましくは0.3〜
6Kgが使用される。しかしながら特別の場合に
は、これらの範囲を超えることが、または下まわ
ることが可能であり、また時には必要でさえあ
る。
本発明は、活性成分として前記一般式()の
ウレアまたはチオウレア系化合物と、BPMC及
びMTMCのうちの一種または二種とを含み、且
つ希釈剤(溶剤および/または増量剤および/ま
たは担体)および/または界面活性剤、更に必要
ならば、例えば安定剤、固着剤、共力剤を含む農
園芸用殺菌組成物が提供される。
更に、本発明は植物病原菌および/またはそれ
らの生育個所に、本発明混合活性化合物を単独
に、または希釈剤(溶剤および/または増量剤お
よび/または担体)および/または界面活性剤、
更に必要ならば例えば、安定剤、固着剤、共力剤
と混合して施用する植物病原菌の防除方法が提供
される。
実施例1 (水和剤)
本発明化合物No.1、5部、BPMC10部、粉末
けい藻土と粉末クレーとの混合物(1:5)、80
部、アルキルベンゼンスルホン酸ナトリウム、2
部、アルキルナフタレンスルホン酸ナトリウムホ
ルマリン縮合物、3部を粉砕混合し、水和剤とす
る。これを水で希釈して、植物病原菌および/ま
たはそれらの生育個所に噴霧処理する。
実施例2 (乳剤)
本発明化合物No.2、5部、MTMC25部、キシ
レン、55部、ポリオキシエチレンアルキルフエニ
ルエーテル、8部、アルキルベンゼンスルホン酸
カルシウム、7部を混合撹拌して乳剤とする。こ
れらを水で希釈して植物病原菌および/またはそ
れらの生育個所に噴霧処理する。
実施例3 (粉剤)
本発明化合物No.1、1部、MTMC1部粉末クレ
ー、98部を粉砕混合して粉剤とする。これを植物
病原菌および/またはそれらの生育個所に散粉す
る。
実施例4 (粉剤)
本発明化合物No.1、1部、MTMC,0.5部、
BPMC,0.5部、粉末クレー、98部を粉砕混合し
て粉剤とする。これを植物病原菌および/または
それらの生育個所に散粉する。
実施例5 (粉剤)
本発明化合物No.2、1部、BPMC1.5部、イソ
プロピルハイドロゲンホスフエート(PAP)、0.5
部、粉末クレー、97部を粉砕混合して粉剤とし、
植物病原菌および/またはそれらの生育個所に散
粉する。
実施例6 (粒剤)
本発明化合物No.1、2部、MTMC8部ベントナ
イト(モンモリロナイト)、30部、タルク(滑
石)、58部、リグニンスルホン酸塩、2部の混合
物に、水、25部を加え良く〓化し、押し出し式造
粒機により、10〜40メツシユの粒状として40〜50
℃で乾燥して粒剤とする。これを植物病原菌およ
び/またはそれらの生育個所に散粒する。
実施例7 (粉剤)
本発明化合物No.2、1部、MTMC,1.0部、
BPMC,0.5部イソプロピルハイドロゲンホスフ
エート(PAP)、0.5部、粉末クレー、97部を粉砕
混合して粉剤とし、植物病原菌および/またはそ
れらの生育個所に散粉する。
実施例8 (粒剤)
0.2〜2mmに粒径分布を有する粘土鉱物粒、95
部を回転混合機に入れ回転下、有機溶剤に溶解さ
せた本発明化合物No.2、1部、MTMC、4部を
噴霧し均等にしめらせた後40〜50℃で乾燥して粒
剤とする。これを植物病原菌および/またはそれ
らの生育個所に散粒する。
文献によりすでに公知の活性化合物と比較した
際、本発明による混合活性化合物は、効果が実質
的に改善されたこと、並びに温血動物に対して毒
性が非常に低いことに特徴があり、従つて該化合
物は非常に利用価値がある。
本発明の混合活性化合物の予想以上にすぐれた
点および著しい効果を、稲紋枯病菌に対して使用
した以下の試験結果から認めることができる。
試験例 1
稲紋枯病に対する防除効果試験(ポツト試験)
供試混合活性化合物の調製
所定濃度比の混合活性化合物:50重量部
担 体:珪藻土とカオリンとの混合物
(1:5) 45重量部
乳化剤:ポリオキシエチレンアルキルフエニルエ
ーテル 5重量部
上述した量の混合活性化合物、担体および乳化
剤を粉砕混合して水和剤とし、その所定薬量を水
で希釈して調製する。
試験方法
水稲(品種:金南風)を直径15cmの磁製ポツト
に湛水状態で栽培し、その幼穂形成期に、上記の
様に調製した供試混合活性化合物の所定濃度希釈
液を、3ポツト当り100mlの割合で散布した。
散布の翌日、供試イネ植物体の株元に、大麦培
地で10日間培養して菌核を形成した紋枯病菌を接
種し、温度28〜30℃、相対湿度95%以上の湿室に
10日間保つて発病させた後、発病程度と薬害の有
無を調査した。調査は、株元の接種部分からの病
斑伸長により次の基準で被害度を表わした。
被害度=3n3+2n2+n1+n0/3N×100
但し、N :全調査茎数
n0:無発病茎数
n1:第1葉位葉鞘(下から)まで罹病した茎数
n2:第2葉位葉鞘(下から)まで罹病した茎数
n3:第3葉位葉鞘(下から)以上まで罹病した
茎数
更に被害度より次式により防除価を求めた。
防除価(%)=(無処理区の被害度)−(処理区の被
害度)/(無処理区の被害度)×100
第1表に試験結果(防除価%)を示す。
The present invention has the general formula: [In the formula, R is a branched alkyl group having 3 to 8 carbon atoms or a cycloalkyl group having 5 to 8 carbon atoms, X is a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 4 carbon atoms, and Y is Indicates an oxygen or sulfur atom. ] Urea or thiourea compounds represented by O-sec-butylphenyl methyl carbamate (hereinafter abbreviated as BPMC), m-tolyl methyl carbamate (hereinafter abbreviated as MTMC)
The present invention relates to an agricultural and horticultural fungicide characterized by containing one or two of the above as active ingredients. In order to develop a new agricultural and horticultural fungicide, the present inventors have studied a mixed preparation that has the effect of cooperatively and synergistically increasing the effects of drugs by mixing drugs with different effects. I've been repeating it. The present inventors have now discovered that the fungus has extremely excellent bactericidal activity, especially against rice sheath blight (Pellicularia sasakii).
A urea or thiourea compound represented by the general formula () that exhibits an excellent effect on
When mixed with one or two of BPMC and MTMC, which exhibit excellent insecticidal effects, the bactericidal effect of the urea or thiourea compound represented by the general formula () increases cooperatively and synergistically. discovered. When the agricultural and horticultural fungicide of the present invention is used to control plant diseases, the concentration of the urea or thiourea compound represented by the above general formula () is within a range that does not exhibit an accurate control effect when used as a single agent. It was found that even in the case of phytopathogens, this mixture exerted extremely pronounced synergistic and synergistic effects, resulting in increased bactericidal ability against plant pathogens and accurate control. In addition, since the effects of each single agent appear at the same time, it is possible to expand the bactericidal spectrum and simultaneously control harmful insects, which has been confirmed to be effective in terms of labor saving and economic efficiency in agriculture. In recent years, the emergence of harmful insects that have acquired drug resistance has become a major problem.In such situations, in order to control harmful insects and plant diseases at the same time, it is necessary to use compounds of the general formula () above. , m-tolylpropyl carbamate, O-sec-butylphenylpropyl carbamate, and S-(2-ethylthio)ethyl dipropyl thiophosphate. This can be easily achieved, and by mixing synergistic effects also appear, which can be exploited more advantageously. Specifically, the urea or thiourea compounds represented by the general formula () include N-4-chlorobenzyl N-sec-butyl N'-phenylurea (or thiourea), N-4-chlorobenzyl N-cyclopentyl
N'-phenylurea (or thiourea), N-4-methylbenzyl N-cyclopentyl
N'-phenylurea (or thiourea), N-4-nitrobenzyl N-cyclopentyl
N'-phenylurea (or thiourea), N-4-cyanobenzyl N-cyclopentyl
N'-phenylurea (or thiourea), N-4-chlorobenzyl N-isopropyl N'-
Phenylurea (or thiourea), N-4-bromobenzyl N-isopropyl N'-
Phenylurea (or thiourea), etc. can be mentioned. The agricultural and horticultural fungicide of the present invention has low toxicity to warm-blooded animals and good affinity for higher plants, that is, it has the characteristics that it does not cause any phytotoxicity to cultivated plants at normal concentrations. It can be used quite conveniently for the simultaneous control of plant diseases caused by pathogenic bacteria and of plant diseases and harmful insects. When using the agricultural and horticultural fungicide of the present invention, it can be used as it is by diluting it directly with water, or it can be made into various formulations by using agricultural chemical auxiliaries and methods commonly used in the field of agricultural chemical manufacturing. be able to. In actual use, these various formulations can be used directly or diluted with water to a desired concentration. The pesticide adjuvants referred to here include, for example, diluents (solvents, fillers, carriers), surfactants (solubilizers,
emulsifiers, dispersants, wetting agents), stabilizers, fixing agents, propellants for aerosols, and synergists. Solvents include water: organic solvent; hydrocarbons [e.g., n-hexane, petroleum ether, naphtha, petroleum fractions (paraffin wax, kerosene, light oil, medium oil, heavy oil), benzene, toluene, xylenes], halogenated Hydrocarbons [e.g. chlormethylene, carbon tetrachloride, trichlorethylene, ethylene chloride, ethylene dibromide, chlorobenzene chloroform], alcohols [e.g. methyl alcohol, ethyl alcohol, propyl alcohol, ethylene glycol], ethers , [e.g. ethyl ether, ethylene oxide, dioxane],
Alcohol ethers [e.g. ethylene glycol monomethyl ether], ketones [e.g.
acetone, isophorone], esters, [e.g.
Ethyl acetate, amyl acetate], amides, [e.g.
dimethylformamide, dimethylacetamide],
Mention may be made of sulfoxides, such as dimethyl sulfoxide. Inorganic granules as fillers or carriers; sulfur, slaked lime, magnesium lime, gypsum, calcium carbonate, silica, perlite, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zeolite,
Clay minerals (e.g. pyrophyllite, talc, montmorillonite, beidellite, vermiculite, kaolinite, mica): vegetable powder; shell powder;
Starch, modified starch, sugar, glucose, crushed plant stems: synthetic resin powder; phenolic resin, urea resin, vinyl chloride resin. Examples of the surfactant include anionic surfactants; alkyl sulfates, [e.g. sodium lauryl sulfate], arylsulfonic acids,
[e.g. alkylaryl sulfonates, sodium alkylnaphthalene sulfonates], succinates, polyethylene glycol alkyl aryl ether sulfate salts: cationic surfactants; alkylamines, [e.g.
laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride], polyoxyethylene alkylamines: nonionic surfactants; polyoxyethylene glycol ethers, [e.g., polyoxyethylene alkylaryl ether, and condensates thereof] Examples include polyoxyethylene glycol esters, [eg, polyoxyethylene fatty acid ester], polyhydric alcohol esters, [eg, polyoxyethylene sorbitan monolaurate]: amphoteric surfactants, and the like. In addition, stabilizers, fixing agents [e.g., agricultural soap, caseinate lime, sodium alginate, polyvinyl alcohol (PVA), vinyl acetate adhesives, acrylic adhesives], propellants for aerosols [e.g.
Trichlorofluoromethane, dichlorofluoromethane, 1,2,2-trichloro-1,1,2-trifluoroethane, chlorobenzene, LNG, lower ether]: Combustion regulator (for smoking agents) [e.g.
Nitrite, zinc dust, dicyandiamide]: oxygen supplying agent (oxygenyielding) [e.g. chlorate,
Dichromate]: Phytotoxicity reducer [e.g., zinc sulfate,
Ferrous chloride, copper nitrate]: Potency extenders: Dispersion stabilizers [eg, casein, tragacanth, carboxymethyl cellulose (CMC), polyvinyl alcohol (PVA)]: Synergists can be mentioned. The mixed active compound of the present invention can be manufactured into various formulations by methods generally practiced in the agricultural chemical manufacturing field. Forms of preparations include emulsions, oils, wettable powders, aqueous solutions, suspensions, powders, granules, powders, smoking agents, tablets, aerosols, pastes, capsules, etc. can. The agricultural and horticultural fungicide of the present invention contains the above-mentioned active ingredient.
It can be contained in an amount of 0.1 to 95% by weight, preferably 0.5 to 90% by weight. In actual use, the various formulations and spray preparations described above (ready-to-use)
The active compound content in the preparation is generally
0.0001-20% by weight, preferably 0.005-10% by weight
A range of is appropriate. The content of these active ingredients can be appropriately changed depending on the form of the preparation, the application method, purpose, timing, place, and the occurrence of pathogenic bacteria or pathogenic bacteria and harmful insects. The mixed active compounds of the invention may further, if necessary,
Other pesticides, such as insecticides, fungicides, acaricides,
Nematicides, antiviral agents, herbicides, plant growth regulators, attractants, [e.g., organophosphate compounds, carbamate compounds, dithio (or thiol) carbamate compounds, organochlorine compounds, dinitro compounds] , organic sulfur or metal compounds, antibiotics, substituted diphenyl ether compounds, urea compounds, triazine compounds] or/and fertilizers, etc. may also be present. Various formulations or ready-to-use preparations containing the mixed active ingredients of the invention are available.
Prepara-tion) refers to application methods commonly used in the field of agrochemical manufacturing, such as spraying, spraying, misting, atomizing, dusting, granulation, water surface application, and pouring. pouring)]: fumigation: soil application, [e.g., incorporation, sprinkleling, vaporing, irrigation]: surface application, [e.g.
Coating, banding, dressing, coating〕: Soaking:
This can be done by baiting, etc. Also, the so-called ultra-low-concentration spraying method (ultra-low-
volume) can also be used. In this way it is possible to have 100% active ingredient content. The application rate per unit area is approximately 0.03 to 10 Kg of active compound per hectare, preferably 0.3 to 10 Kg of active compound per hectare.
6Kg is used. However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges. The present invention comprises as an active ingredient a urea or thiourea compound of the general formula () and one or two of BPMC and MTMC, and a diluent (solvent and/or filler and/or carrier) and An agricultural and horticultural fungicidal composition is provided which contains a surfactant and, if necessary, a stabilizer, a fixing agent, and a synergist. Furthermore, the present invention provides for the application of the combined active compounds of the present invention to plant pathogens and/or their growth sites, either alone or in combination with diluents (solvents and/or fillers and/or carriers) and/or surfactants,
Furthermore, if necessary, a method for controlling plant pathogenic bacteria is provided, which is applied in combination with, for example, a stabilizer, a fixing agent, or a synergist. Example 1 (Wettable powder) Compound No. 1 of the present invention, 5 parts, BPMC 10 parts, mixture of powdered diatomaceous earth and powdered clay (1:5), 80 parts
Part, sodium alkylbenzenesulfonate, 2
1 part and 3 parts of sodium alkylnaphthalene sulfonate formalin condensate were pulverized and mixed to prepare a wettable powder. This is diluted with water and sprayed onto plant pathogens and/or their growth areas. Example 2 (Emulsion) 5 parts of the present compound No. 2, 25 parts of MTMC, 55 parts of xylene, 8 parts of polyoxyethylene alkyl phenyl ether, and 7 parts of calcium alkylbenzenesulfonate are mixed and stirred to form an emulsion. . These are diluted with water and sprayed onto plant pathogens and/or their growth areas. Example 3 (Powder) 1 part of Compound No. 1 of the present invention, 1 part of MTMC, and 98 parts of powdered clay were pulverized and mixed to prepare a powder. This is sprinkled on plant pathogens and/or their growth areas. Example 4 (Powder) Compound No. 1 of the present invention, 1 part, MTMC, 0.5 part,
Grind and mix 0.5 parts of BPMC and 98 parts of powdered clay to make a powder. This is sprinkled on plant pathogens and/or their growth areas. Example 5 (Powder) Compound No. 2 of the present invention, 1 part, BPMC 1.5 parts, isopropyl hydrogen phosphate (PAP), 0.5 parts
1 part, powdered clay, 97 parts were ground and mixed to make a powder,
Sprinkle dust on plant pathogens and/or their growth areas. Example 6 (Granules) A mixture of Compound No. 1 of the present invention, 2 parts, 8 parts of MTMC, 30 parts of bentonite (montmorillonite), 58 parts of talc, 2 parts of lignin sulfonate, and 25 parts of water. Add 10 to 40 mesh granules, mix well, and use an extrusion granulator to make 40 to 50 mesh granules.
Dry at ℃ to form granules. This is sprinkled on plant pathogens and/or their growth areas. Example 7 (Powder) Compound No. 2 of the present invention, 1 part, MTMC, 1.0 part,
BPMC, 0.5 parts, isopropyl hydrogen phosphate (PAP), 0.5 parts, and powdered clay, 97 parts, are ground and mixed to make a powder, and the powder is sprinkled on plant pathogens and/or their growth areas. Example 8 (Granules) Clay mineral particles having a particle size distribution of 0.2 to 2 mm, 95
1 part of Compound No. 2 of the present invention dissolved in an organic solvent and 4 parts of MTMC were sprayed into a rotary mixer and dried at 40 to 50°C to form granules. do. This is sprinkled on plant pathogens and/or their growth areas. When compared with active compounds already known from the literature, the mixed active compounds according to the invention are distinguished by a substantially improved efficacy, as well as by a very low toxicity for warm-blooded animals, and therefore The compound is of great utility. The unexpected superiority and remarkable efficacy of the mixed active compounds of the present invention can be seen from the following test results when used against rice sheath blight fungi. Test example 1 Control effect test against rice sheath blight (pot test)
Preparation of test mixed active compound Mixed active compound at predetermined concentration ratio: 50 parts by weight Carrier: mixture of diatomaceous earth and kaolin (1:5) 45 parts by weight Emulsifier: polyoxyethylene alkyl phenyl ether 5 parts by weight Above-mentioned amount A wettable powder is prepared by grinding and mixing the mixed active compound, carrier and emulsifier, and diluting the prescribed amount with water. Test method Paddy rice (variety: Jinnanfeng) was cultivated in a porcelain pot with a diameter of 15 cm under water, and during the panicle formation period, a diluted solution of a predetermined concentration of the test mixed active compound prepared as above was added to the pot. It was sprayed at a rate of 100ml per pot. The day after spraying, the roots of the test rice plants were inoculated with sheath blight bacteria that had been cultured in barley medium for 10 days to form sclerotia, and placed in a humid room at a temperature of 28-30℃ and a relative humidity of 95% or higher.
After keeping the plants for 10 days and allowing them to develop the disease, the degree of disease onset and the presence or absence of drug damage were investigated. In the survey, damage was expressed based on the following criteria based on the growth of lesions from the inoculated part of the plant. Degree of damage = 3n 3 +2n 2 +n 1 +n 0 /3N×100 However, N: Total number of stems surveyed n 0 : Number of disease-free stems n 1 : Number of stems affected up to the first leaf sheath (from the bottom) n 2 : Number of stems infected up to the second leaf sheath (from the bottom) n 3 : Number of stems infected up to the third leaf sheath (from the bottom) Further, the control value was determined from the degree of damage using the following formula. Control value (%) = (Damage level in untreated area) - (Damage level in treated area) / (Damage level in untreated area) x 100 Table 1 shows the test results (control value %).
【表】【table】
【表】
以上、発明の詳細な説明において詳しく説明し
た本発明を具体的に要約すれば次の通りである。
(1) 一般式:
〔式中、
Rは炭素原子数3〜8の分岐アルキル基また
は炭素原子数5〜8のシクロアルキル基、
Xはハロゲン原子、ニトロ基、シアノ基また
は炭素原子数1〜4のアルキル基、
Yは酸素原子またはイオウ原子を示す。〕
で表わされるウレアまたはチオウレア系化合物
と、O―sec―ブチルフエニルメチルカーバメ
イト、(以下、BPMCと略記する)、m―トリ
ルメチルカーバメイト(以下、MTMCと略記
する)のうちの一種、または二種とを、有効成
分として含有することを特徴とする農園芸用殺
菌剤。
(2) 前記一般式()と、BPMC,MTMCのう
ちの一種、または二種との混合活性化合物の植
物病害防除のための有効量を植物病原菌およ
び/またはその生育場所に施用する植物病害の
防除方法。
(3) 前記混合活性化合物を単独で用いるか、また
は混合活性化合物を希釈剤(溶剤および/また
は増量剤および/または担体)および/または
界面活性剤、更に必要ならば例えば、安定剤、
固着剤、共力剤と混合することにより、その混
合物を0.0001〜20重量%、好ましくは0.005〜
10重量%含有する調製薬剤を用いる前記(2)項の
防除方法。
(4) 前記混合活性化合物の施用量が1ヘクタール
当り約0.03〜10Kg、好ましくは0.3〜6Kgであ
る前記(2)項の防除方法。[Table] The present invention, which has been explained in detail in the detailed description of the invention, is specifically summarized as follows. (1) General formula: [In the formula, R is a branched alkyl group having 3 to 8 carbon atoms or a cycloalkyl group having 5 to 8 carbon atoms, X is a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 4 carbon atoms, Y represents an oxygen atom or a sulfur atom. ] A urea or thiourea compound represented by and one or two of O-sec-butylphenyl methyl carbamate (hereinafter abbreviated as BPMC), m-tolyl methyl carbamate (hereinafter abbreviated as MTMC) An agricultural and horticultural fungicide characterized by containing seeds as an active ingredient. (2) A method for controlling plant diseases in which an effective amount of a mixed active compound of the general formula () and one or two of BPMC and MTMC is applied to plant pathogens and/or their growth sites. Control methods. (3) The mixed active compounds are used alone or combined with diluents (solvents and/or fillers and/or carriers) and/or surfactants and, if necessary, stabilizers, e.g.
By mixing with a fixing agent and a synergist, the mixture can be reduced to 0.0001 to 20% by weight, preferably 0.005 to 20% by weight.
The pest control method according to item (2) above, using a prepared chemical containing 10% by weight. (4) The pest control method according to item (2) above, wherein the applied amount of the mixed active compound is about 0.03 to 10 kg per hectare, preferably 0.3 to 6 kg.
Claims (1)
炭素原子数5〜8のシクロアルキル基、 Xはハロゲン原子、ニトロ基、シアノ基または
炭素原子数1〜4のアルキル基、 Yは酸素原子またはイオウ原子を示す。〕 で表わされるウレアまたはチオウレア系化合物
と、O―sec―ブチルフエニルメチルカーバメイ
ト、m―トリルメチルカーバメイトのうちの一
種、または二種とを、有効成分として含有するこ
とを特徴とする農園芸用殺菌剤。[Claims] 1. General formula: [In the formula, R is a branched alkyl group having 3 to 8 carbon atoms or a cycloalkyl group having 5 to 8 carbon atoms, X is a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 4 carbon atoms, Y represents an oxygen atom or a sulfur atom. ] A urea or thiourea compound represented by the following, and one or both of O-sec-butylphenylmethylcarbamate and m-tolylmethylcarbamate, for agricultural and horticultural use, characterized by containing the same as active ingredients. Fungicide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6615279A JPS55160705A (en) | 1979-05-30 | 1979-05-30 | Agricultural and horticultural germicide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6615279A JPS55160705A (en) | 1979-05-30 | 1979-05-30 | Agricultural and horticultural germicide |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS55160705A JPS55160705A (en) | 1980-12-13 |
JPS6348842B2 true JPS6348842B2 (en) | 1988-09-30 |
Family
ID=13307601
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP6615279A Granted JPS55160705A (en) | 1979-05-30 | 1979-05-30 | Agricultural and horticultural germicide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS55160705A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3132690A1 (en) * | 1981-08-19 | 1983-03-17 | Bayer Ag, 5090 Leverkusen | (THIO) UREAS, A METHOD FOR THEIR PRODUCTION, THEIR USE AS A PLANT PROTECTION AGENT AND INTERMEDIATE PRODUCTS FOR THEIR PRODUCTION |
-
1979
- 1979-05-30 JP JP6615279A patent/JPS55160705A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS55160705A (en) | 1980-12-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR920002790B1 (en) | Process for the preparation of n-benzyl cyclopropane carboxamide | |
JPH07267807A (en) | Composition and method for adjusting growth of plant | |
JPS6348842B2 (en) | ||
JPS6027642B2 (en) | Fungicide for agriculture and horticulture | |
JPS636522B2 (en) | ||
JPH0764688B2 (en) | Agro-horticultural germicidal composition | |
JPH0149344B2 (en) | ||
JPS6218522B2 (en) | ||
JPH0231066B2 (en) | ||
US4708953A (en) | Salicylamide derivatives | |
JPS6325590B2 (en) | ||
KR920002793B1 (en) | Process for preparing benzylurea derivatives | |
JPS6160659A (en) | Substituted phenylsulfonylazole, its production, and agricultural and horticultural fungicide | |
JPS6332762B2 (en) | ||
JPH0420434B2 (en) | ||
JPS5920206A (en) | Herbicide | |
JPS638922B2 (en) | ||
JPS6350350B2 (en) | ||
JPS6078966A (en) | Trichloroacryloyloxime derivative, production thereof and agricultural germicide | |
JPS608203A (en) | Agricultural and horticultural fungicide comprising pyrimidine derivative as active ingredient | |
JPS62161707A (en) | Fungicide composition for agricultural and horticultural purpose | |
JPH0254323B2 (en) | ||
JPS6323988B2 (en) | ||
JPS58183688A (en) | Oxadiazole derivative, its preparation and herbicide | |
JPS58188804A (en) | Herbicide |