JPH02229164A - N-(2-chloroisonicotinoyl)imino derivative or fungicide for agricultural and horticultural purposes containing the same - Google Patents
N-(2-chloroisonicotinoyl)imino derivative or fungicide for agricultural and horticultural purposes containing the sameInfo
- Publication number
- JPH02229164A JPH02229164A JP4860889A JP4860889A JPH02229164A JP H02229164 A JPH02229164 A JP H02229164A JP 4860889 A JP4860889 A JP 4860889A JP 4860889 A JP4860889 A JP 4860889A JP H02229164 A JPH02229164 A JP H02229164A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- chloroisonicotinoyl
- agricultural
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 N-(2-chloroisonicotinoyl)imino Chemical class 0.000 title claims abstract description 48
- 239000000417 fungicide Substances 0.000 title claims abstract description 12
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 5
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 25
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 150000003585 thioureas Chemical class 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 241000209094 Oryza Species 0.000 description 16
- 235000007164 Oryza sativa Nutrition 0.000 description 16
- 235000009566 rice Nutrition 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000008187 granular material Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000003902 lesion Effects 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000007884 disintegrant Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- DEMJOLRJLACBRX-UHFFFAOYSA-N 2-chloropyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC(Cl)=C1 DEMJOLRJLACBRX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 241000519695 Ilex integra Species 0.000 description 2
- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 241000231139 Pyricularia Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides 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
- 239000010775 animal oil Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000008346 aqueous phase Substances 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
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000012267 brine Substances 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
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 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 1
- 239000003085 diluting agent Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000004503 fine granule Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- WBNYPYHDITWHHM-UHFFFAOYSA-N n-[bis(methylsulfanyl)methylidene]pyridine-3-carboxamide Chemical compound CSC(SC)=NC(=O)C1=CC=CN=C1 WBNYPYHDITWHHM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical group C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新規なN−(2−クロロイソニコチノイル)イ
ミノ誘導体に関し、該誘導体は、水田、畑地または果樹
園などにおける農園芸用殺菌剤として用いることができ
る。[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a novel N-(2-chloroisonicotinoyl)imino derivative, which can be used as an agricultural and horticultural fungicide in paddy fields, fields, orchards, etc. It can be used as
これまで、N−(2−り゛ロロインニコチノイル)イミ
ノ誘導体が、農園芸用殺菌剤として有用であることは、
何ら知られていない。Until now, it has been known that N-(2-lyroloinnicotinoyl)imino derivatives are useful as agricultural and horticultural fungicides.
nothing is known.
N−(ピリジルカルボニル)イミノ誘導体としては、N
−ニコチノイルカルボンイミドジチオ酸ジメチルの合成
例が、シノセシス(5ynthesis ) 1981
、 554に記載されており、また、Nピリドイル−
(2)−N’−フェニル−8−メチルイソチオ尿素の合
成例が、東ドイツ特許241411号に記載されている
が、生理活性などについて具体的には何ら記載されてい
ない。As the N-(pyridylcarbonyl)imino derivative, N
- An example of the synthesis of dimethyl nicotinoylcarbonimidodithioate was published in Synthesis 1981.
, 554, and also N-pyridoyl-
(2) An example of the synthesis of -N'-phenyl-8-methylisothiourea is described in East German Patent No. 241411, but there is no specific description of its physiological activity.
これまで農園芸作物の植物病害に対し、多くの防除剤が
使用されているが、その効力が不充分であったり、薬剤
耐性菌の出現によりその使用が制限されたり、作物に薬
害を生じたり、また経済性に問題があるなどの欠点を有
している。Many pesticides have been used to treat plant diseases in agricultural and horticultural crops, but their efficacy is insufficient, their use is limited due to the emergence of drug-resistant bacteria, and their use may be limited due to the emergence of drug-resistant bacteria. , and also has disadvantages such as economical problems.
前記課題を解決するために、鋭意研究した結果、後記−
設入〔1〕で表わされるN−(2−クロロインニコチノ
イル〕イミノ誘導体が、従来の農園芸用殺菌剤の欠点を
補い高い防除効果を示すと共に、植物体に薬害などの悪
影響を及ぼさないことを見い出し、本発明を児成するに
至った。In order to solve the above problem, as a result of intensive research, the following -
The N-(2-chloroinnicotinoyl)imino derivative represented by [1] compensates for the shortcomings of conventional agricultural and horticultural fungicides, exhibits high pesticidal effects, and does not have any adverse effects such as phytotoxicity on plants. This discovery led to the creation of the present invention.
すなわち、本発明は一般式
〔式中、XおよびYは、それぞれ独立に、酸素原子、イ
オウ原子、イミノ基、または、メチルイミノ基(ただし
XおよびYは同時に酸素原子であるととはない。)を示
し、R1およびR2は、それぞれ独立に、低級アルキル
基、低級シアノアルキル基、アリル基、プロパルギル基
、フェニル基、または2−ピリジル基を示す。また、R
′とR2は÷CH,,九で結合し、環状構造をとること
もでき、ここで、nは2または3を示し、まることもで
き、ここでZは水素原子または塩素原子を示し、tとm
はOまたは1であり、かつt 十m = Qまたは1を
示す。〕で表わされるN(2−クロロイソニコチノイル
)イミノ誘導体に関する。That is, the present invention is based on the general formula [where X and Y are each independently an oxygen atom, a sulfur atom, an imino group, or a methylimino group (however, X and Y are not simultaneously oxygen atoms). and R1 and R2 each independently represent a lower alkyl group, a lower cyanoalkyl group, an allyl group, a propargyl group, a phenyl group, or a 2-pyridyl group. Also, R
' and R2 are bonded by ÷CH,,9, and can also form a cyclic structure, where n represents 2 or 3, and can also be a circle, where Z represents a hydrogen atom or a chlorine atom, and t and m
is O or 1, and indicates t 10m = Q or 1. The present invention relates to an N(2-chloroisonicotinoyl)imino derivative represented by the following.
本発明の一般式(1)の化合物は以下の方法で製造する
ことができる。The compound of general formula (1) of the present invention can be produced by the following method.
)製法■
〔式中Xは酸素原子、イオウ原子、イミノ基、またはメ
チルイミノ基を示し、R3およびR4はそれぞれ独立に
低級アルキル基、低級シアノアルキル基、アリル基、プ
ロパルギル基、フェニル基または2−ピリジル基を示し
、Qはハロゲン原子を示す。〕
一般式(II)で表わされるチオカルバミノ酸エステル
、ジチオカルバミン酸エステルマタはチオ尿素誘導体を
、例えば水素化すトリウムなどのアルカリ金属水素化物
、ナトリウムメチラートなどのアルカリ金属アルコラー
ド、水酸化ナトリウムなどのアルカリ金属水酸化物、炭
酸カリウムなどのアルカリ炭酸塩などの塩基の存在下、
例えばエーテル、テトラヒドロフランなどのエーテル類
、アセトニトリルなどのニトリル類、べ/ゼ/、トルエ
ンなどの芳香族炭化水素類、ジメチルホルムアミド、ジ
メチルスルホキシドなどの非プロトン性極性溶媒、また
は、これらの混合溶媒を溶媒として、−設入R4 Qで
表わされるハロゲン化物と通常−20°C〜120°C
,好ましくは一10°C〜600Cで、1〜6時間反応
させることにより、−設入(II)で表わされるN〜(
2−クロロイソニコチノイル)イミノ誘導体が得られる
。) Manufacturing method ■ [In the formula, X represents an oxygen atom, a sulfur atom, an imino group, or a methylimino group, and R3 and R4 each independently represent a lower alkyl group, a lower cyanoalkyl group, an allyl group, a propargyl group, a phenyl group, or a 2- It represents a pyridyl group, and Q represents a halogen atom. ] Thiocarbamate esters and dithiocarbamate esters represented by general formula (II) are thiourea derivatives, for example, alkali metal hydrides such as thorium hydride, alkali metal alcoholades such as sodium methylate, alkali metal water such as sodium hydroxide, etc. In the presence of bases such as oxides, alkali carbonates such as potassium carbonate,
For example, ethers, ethers such as tetrahydrofuran, nitriles such as acetonitrile, aromatic hydrocarbons such as benzene, toluene, aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, or a mixed solvent thereof are used as solvents. As, -introduced R4 with a halide represented by Q and usually at -20°C to 120°C.
, preferably at -10° C. to 600° C. for 1 to 6 hours.
A 2-chloroisonicotinoyl)imino derivative is obtained.
11)製法■
6一
〔式中Xは前記と同じ意味を有し、R′、 R’および
R5は、Xがイオウ原子である場合はR3とR4は同一
の、Xが酸素原子、イミノ基またはメチルイミノ基であ
る場合は同一または異なっていてもよい低級アルギル基
、低級シアノアルキル基、アリル基、プロパルギル基、
フェニル基、または2−ピリジル基を示し、R5は水素
原子またはメチル基を示し、R6は水素原子またはメチ
ル基を示す。〕
一般式(][1,)で表わされるN−(2−クロロイソ
ニコチノイル)イミノ誘導体を一般式I(′R6Nl−
1で表わされるアミン類と、例えばベンゼン、トルエン
などの芳香族炭化水素類、ヘキサンなどの脂肪族炭化水
素類、クロロホルムなどの・・ロゲノ化炭化水素類、メ
タノールなどのアルコール類、エーテル、テトラヒドロ
フラノなどのエーテル類、アセトニトリルなどのニトリ
ル類、酢酸エチルなどのエステル類、ジメチルホルム−
アミド、ジメチルスルホキシドなどの非プロトン性極性
溶媒、またはこれらの混合溶媒を溶媒として、通常は一
200C〜1.500C1好ましくは000〜120°
Cで1〜8時間反応させることにより、−設入(IV)
で表わされるN−(2−クロロイソニコチノイル)イミ
ノ誘導体が得られる。11) Manufacturing method ■ 6- [In the formula, X has the same meaning as above, R', R' and R5 are the same when X is a sulfur atom, R3 and R4 are the same, or in the case of a methylimino group, lower argyl groups, lower cyanoalkyl groups, allyl groups, propargyl groups, which may be the same or different;
It represents a phenyl group or a 2-pyridyl group, R5 represents a hydrogen atom or a methyl group, and R6 represents a hydrogen atom or a methyl group. ] The N-(2-chloroisonicotinoyl)imino derivative represented by the general formula (][1,) is converted into the N-(2-chloroisonicotinoyl)imino derivative represented by the general formula I('R6Nl-
Amines represented by 1, aromatic hydrocarbons such as benzene and toluene, aliphatic hydrocarbons such as hexane, logenated hydrocarbons such as chloroform, alcohols such as methanol, ether, and tetrahydrofurano. ethers such as, nitriles such as acetonitrile, esters such as ethyl acetate, dimethylform-
Using an aprotic polar solvent such as amide, dimethyl sulfoxide, or a mixed solvent thereof, the temperature is usually -200C to 1.500C1, preferably 000 to 120°.
-Incorporation (IV) by reacting for 1 to 8 hours at C
An N-(2-chloroisonicotinoyl)imino derivative represented by is obtained.
さらに−設入(111,1においてXがイオウ原子であ
る場合には、2倍モル以上のアミ7 R5R6NI(の
化合物を合成するととができる。Furthermore, when X is a sulfur atom in -installation (111,1), it is possible to synthesize a compound with twice or more mole of ami7 R5R6NI (.
川)製法■
(’1
〔式中R’、 Qは前記と同じ意味を有し、■(7は
、+CIJ2+。を示し、ここでnは2または3を示す
。〕
式(八〇で表わされる2−クロロイソニコチノイルドと
、二硫化炭素および一設入R’ Qで表わされる)・ロ
ゲノ化物を溶媒存在下で、例えば水素化ナトリウムなど
のアルカリ金属水素化物または、水酸化ナトリウムなど
のアルカリ金属水酸化物などの塩基と一20°C〜12
00C1好ましくは一10°C〜600CでJ〜6時間
反応させることにより、−設入(Vl)で表わされるN
−(2−クロロインニコチノイル)イミノ誘導体が得ら
れる。川) Manufacturing method ■ ('1 [In the formula, R' and Q have the same meanings as above, ■ (7 indicates +CIJ2+, where n indicates 2 or 3.)] Formula (represented by 80 2-chloroisonicotinoyl, carbon disulfide, and a rogenoide (represented by R' With a base such as an alkali metal hydroxide at -20°C to 12°C
00C1 Preferably, by reacting at -10°C to 600C for J to 6 hours, -N expressed as (Vl)
A -(2-chloroinnicotinoyl)imino derivative is obtained.
ここでいう溶液としては、例えばエーテル、テトラヒド
ロフラノなどのエーテル類、ジメチルホルムアミド、ジ
メチルスルホキシドなどの非プロトン性極性溶媒、アセ
トニトリルなどのニトリル類、ベノゼ/、トルエンなど
の芳香族炭化水素類、または、これらの混合溶媒を用い
ることができる。The solution here includes, for example, ethers such as ether and tetrahydrofurano, aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide, nitriles such as acetonitrile, aromatic hydrocarbons such as benoise, toluene, etc. A mixed solvent of these can be used.
一設入n、4.Qのかかりに、−設入Q−T(”Qを用
い、同様に反応させることにより、−設入(Vl+)で
表わされるN−(2−クロロホルムコチノイル)イミノ
誘導体が得られる。1 set entry n, 4. By similarly reacting with -incorporation Q-T ("Q) at the end of Q, an N-(2-chloroformcotinoyl)imino derivative represented by -incorporation (Vl+) can be obtained.
(Vl)
(IX)
〔式中R4およびR6は前記と同じ意味を有し、R8は
÷CI−1,、九を示し、ここで0は2または3こでZ
は水素原子または塩素原子であり、tとmはOまたは1
であり、かつl −1−m = Qまたは1であり、X
′は酸素原子、イミノ基、メチルイミノ基を示す。〕
一般式(vl)で表わされるN−(2−クロロイソニコ
チノイル)イミノ誘導体を一般式(Vll[)で表わさ
れる化合物と、例えばベンゼン、1、ルエノなどの芳香
族炭化水素類、ヘキサンなどの脂肪族炭化水素類、クロ
ロホルムなどのハロゲン化炭化水素類、テトラヒドロフ
ラノ、ジオキサンなどのエーテル類、アセトニトリルな
どのニトリル類、酢酸エチルなどのエステル類、ジメチ
ルホルムアミド、ジメチルスルホキシドなどの非プロト
ン性極性溶媒、または、これらの混合溶媒を溶媒として
、通常は−20°C〜150°C1好ましくは0°C〜
1200Cで3〜10時間反応させることにより、般弐
(J)で表わされるN−(2−クロロインニコチノイル
)イミノ誘導体が得られる。(Vl) (IX) [In the formula, R4 and R6 have the same meanings as above, R8 represents ÷CI-1, 9, where 0 is 2 or 3 and Z
is a hydrogen atom or a chlorine atom, and t and m are O or 1
, and l −1−m = Q or 1, and X
' represents an oxygen atom, an imino group, or a methylimino group. ] An N-(2-chloroisonicotinoyl)imino derivative represented by the general formula (vl) is combined with a compound represented by the general formula (Vll[), aromatic hydrocarbons such as benzene, 1, lueno, etc., hexane, etc. aliphatic hydrocarbons, halogenated hydrocarbons such as chloroform, ethers such as tetrahydrofurano and dioxane, nitriles such as acetonitrile, esters such as ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, etc. , or a mixed solvent of these as a solvent, usually -20°C to 150°C, preferably 0°C to
By reacting at 1200C for 3 to 10 hours, an N-(2-chloroinnicotinoyl)imino derivative represented by Hani (J) is obtained.
■)製法■
〔式中、R’、 R8,XおよびYは前記と同じ意味を
有し、Y′はイオウ原子、イミノ基、またはメチルイミ
ノ基を示す。〕
式(X)で表わされるN−(2−クロロイソニコチノイ
ル)イミドカルボニルクロリドと一般式(XI)で表わ
される化合物を、トリエチルアミンなどのトリアルキル
アミン類やピリジンなどの有機塩基の存在下、例えばエ
ーテル、テトラヒドロフランなどのエーテル類、クロロ
ホルムなどのノ・ロゲン化炭化水素類、ベンゼン、トル
エンなどの芳香族炭化水素類、アセトニトリルなどのニ
トリル類、酢酸エチルなどのエステル類、または、これ
らの混合溶媒を溶媒として、通常は一20°C〜150
℃、好ましくは000〜60°Cで30分〜5時間反応
させることにより、一般弐(X[l)で表わされるN−
(2−クロロインニコチノイル)イミノ誘導体が得られ
る。(2) Production method (2) [In the formula, R', R8, X and Y have the same meanings as above, and Y' represents a sulfur atom, an imino group, or a methylimino group. ] N-(2-chloroisonicotinoyl)imidocarbonyl chloride represented by formula (X) and a compound represented by general formula (XI) in the presence of a trialkylamine such as triethylamine or an organic base such as pyridine, For example, ethers such as ether and tetrahydrofuran, non-rogenated hydrocarbons such as chloroform, aromatic hydrocarbons such as benzene and toluene, nitriles such as acetonitrile, esters such as ethyl acetate, or mixed solvents thereof. as a solvent, usually from -20°C to 150°C.
By reacting at 000 to 60°C for 30 minutes to 5 hours, N-
A (2-chloroinnicotinoyl)imino derivative is obtained.
一般式(XI)で表わされる化合物のかわりに、一般弐
(Xll)で表わされる化合物を用い、同様に反応させ
ることにより、−紋穴〇dV)で表わされるN−(2−
クロロイソニコチノイル)イミノ誘導体が得られる。By using a compound represented by general formula (Xll) instead of the compound represented by general formula (XI) and reacting in the same manner, N-(2-
A chloroisonicotinoyl)imino derivative is obtained.
式(X)で表わされるN−(2−クロロイソニコチノイ
ル)イミドカルボニルクロリドは、2−クロロインニコ
チノイルインチアシナトの、ジクロロメタン、クロロホ
ルムなどのハロゲン化炭化水素系溶媒の溶液中に、通常
は一20°C〜20°Cで、過剰量の塩素ガスを吹き込
み、その後さらに、1〜4時間攪拌することにより、高
収率で得ることができるとともに、精製工程をへること
なく、そのまま次工程に用いることもできる。N-(2-chloroisonicotinoyl)imidocarbonyl chloride represented by formula (X) is usually prepared by adding 2-chloroinnicotinoyl inthiacinate to a solution of a halogenated hydrocarbon solvent such as dichloromethane or chloroform. can be obtained in high yield by blowing in an excess amount of chlorine gas at -20°C to 20°C and then further stirring for 1 to 4 hours. It can also be used in the next step.
以上のようにして得られる反応混合物から、目的物を単
離するには、溶媒を減圧留去した残渣か、または、反応
混合物に、酢酸エチルのような有機溶媒を加え抽出し、
水洗乾燥後、場合により有機溶媒を減圧留去するだけで
もよ(、必要により、さらに再結晶あるいはカラムクロ
マトグラフィーにより精製を行う。In order to isolate the target product from the reaction mixture obtained as described above, the solvent is distilled off under reduced pressure and an organic solvent such as ethyl acetate is added to the residue or the reaction mixture is extracted.
After washing with water and drying, the organic solvent may be simply distilled off under reduced pressure (if necessary, further purification is performed by recrystallization or column chromatography).
本発明の一般式(1)において、少なくともXかYのど
ちらか一方がイミノ基である場合は、下記式で表わされ
るように、互変異性体を含む。In the general formula (1) of the present invention, when at least either X or Y is an imino group, tautomers are included as represented by the following formula.
=13−
さらに、本発明は、一般弐(1)で表わされるN−(2
−クロロイソニコチノイル)イミノ誘導体を有効成分と
して含有することを特徴とする農園芸用殺菌剤を提供す
るものである。=13-Furthermore, the present invention provides N-(2
The present invention provides an agricultural and horticultural fungicide characterized by containing a -chloroisonicotinoyl)imino derivative as an active ingredient.
本発明化合物を農園芸用殺菌剤の有効成分として使用す
る場合、本発明化合物を1種又は2種以上使用してもよ
い。When using the compound of the present invention as an active ingredient of a fungicide for agriculture and horticulture, one or more compounds of the present invention may be used.
本発明化合物を農園芸用殺菌剤として使用する場合、使
用目的に応じてそのままか、または効果を助長あるいは
安定にするために農薬補助剤を混用して、農薬製造分野
において一般に行われている方法により、粉剤、細粒剤
、粒剤、水和剤、フロアブル剤および乳剤等の製造形態
にして使用することができる。When the compound of the present invention is used as a fungicide for agricultural and horticultural purposes, depending on the purpose of use, it may be used as is, or it may be mixed with an agrochemical adjuvant to enhance or stabilize the effect, using methods commonly used in the field of agrochemical manufacturing. Accordingly, it can be used in the production form of powders, fine granules, granules, wettable powders, flowable preparations, emulsions, etc.
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、または水で所望の濃度に希釈して使用す
ることができる。In actual use, these various formulations can be used directly or diluted with water to a desired concentration.
−14=
ここにいう農薬補助剤としては担体(希釈剤)およびそ
の他の補助剤たとえば展着剤、乳化剤、湿展剤、分散剤
、固着剤、崩壊剤等をあげることができる。-14= The agrochemical auxiliary agents mentioned herein include carriers (diluents) and other auxiliary agents such as spreading agents, emulsifiers, wetting agents, dispersing agents, fixing agents, and disintegrants.
液体担体としてはトルエン、キシレン等の芳香族炭化水
素、メタノール、ブタノ一ル、グリコール等のアルコー
ル類、アセトン等のケトン類、ジメチルホルムアミド等
のアミド類、ジメチルスルホキシド等のスルホキシド類
、メチルナフタレノ、シクロヘキサン、動植物油、脂肪
酸、脂肪酸エステル等があげられる。Liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methylnaphthalene, Examples include cyclohexane, animal and vegetable oils, fatty acids, and fatty acid esters.
固体担体としてはクレー カオリン、タルり、珪藻土、
シリカ、炭酸カルシウム、モンモリロナイト、べ/トナ
イト、長石、石英、アルミナ、鋸屑等があげられる。Solid carriers include clay, kaolin, tar, diatomaceous earth,
Examples include silica, calcium carbonate, montmorillonite, beth/tonite, feldspar, quartz, alumina, and sawdust.
また乳化剤または分散剤としては通常界面活性剤が使用
され、たとえば高級アルコールナトリウム、ステアリル
トリメチルアンモニウムクロライド、ポリオキシエチレ
ノアルキルフェニルエーテル、ラウリルベクイン等の陰
イオノ系界面活性剤、陽イオン系界面活性剤、非イオン
系界面活性剤、両性イオン系界面活性剤があげられろ。In addition, surfactants are usually used as emulsifiers or dispersants, such as anionic surfactants such as higher alcohol sodium, stearyltrimethylammonium chloride, polyoxyethylenoalkyl phenyl ether, and laurylvequin, and cationic surfactants. Examples include surfactants, nonionic surfactants, and zwitterionic surfactants.
展着剤としてはポリオキシエチレンノニルフェニルエー
テル、ポリオキシエチレンラウリルエーテル等が、湿展
剤としてはポリオキシエチレンノニルフェニルエーテル
、ジアルキルスルホサクシネート等が、固着剤としては
カルボキシメチルセルローズ、ホリビニルアルコール等
が、崩壊剤としてはりダニ/スルホン酸ナトリウム、ラ
ウリル硫酸ナトリウム等があげられる。Spreading agents include polyoxyethylene nonylphenyl ether, polyoxyethylene lauryl ether, etc. Wetting agents include polyoxyethylene nonylphenyl ether, dialkyl sulfosuccinate, etc., and fixing agents include carboxymethyl cellulose and polyvinyl alcohol. Disintegrants include needle mites/sodium sulfonate, sodium lauryl sulfate, etc.
いずれの製剤もそのまま単独で使用できるのみならず、
他の農園芸用殺菌剤、殺虫剤、植物生長調節剤、殺ダニ
剤と混合I−で使用することもできる。Not only can each formulation be used alone, but
It can also be used in a mixture with other agricultural and horticultural fungicides, insecticides, plant growth regulators, and acaricides.
本発明農園芸用殺菌剤における有効成分化合物含量は、
製剤形態、施用する方法、その他の条件によって種々異
なり場合によっては有効成分化合物のみでもよいが、通
常は0.5〜95%(重量)好ましくは2〜70%(重
量)の範囲である。The active ingredient compound content in the agricultural and horticultural fungicide of the present invention is:
It varies depending on the formulation form, method of application, and other conditions, and in some cases only the active ingredient compound may be used, but it is usually in the range of 0.5 to 95% (by weight), preferably 2 to 70% (by weight).
本発明の殺菌剤は、有効成分濃度が好ましくは10〜4
0 0 0 pI)mで植物の茎葉に散布することが
でき、土壌に散布する場合は有効成分散布量は0.02
〜1 0 kg/l O aが好ましい。The disinfectant of the present invention preferably has an active ingredient concentration of 10 to 4
0 0 0 pI) m can be applied to the leaves of plants, and when applied to soil, the amount of active ingredient applied is 0.02
~10 kg/l Oa is preferred.
本発明の化合物は土壌施用、茎葉散布、種子処理、いず
れの処理方法においても、イネいもち病などの植物糸状
菌病、イネ白葉枯病、キーウリ斑点細菌病などの植物細
菌病に高い防除効果を示し、薬剤耐性菌にも有効で、植
物体に薬害などの悪影響を及ぼさない農園芸用殺菌剤で
ある。The compound of the present invention has a high control effect on plant fungal diseases such as rice blast, bacterial leaf blight of rice, and bacterial leaf spot of Japanese cucumber when applied to soil, foliar spray, or seed treatment. It is an agricultural and horticultural fungicide that is effective against drug-resistant bacteria and does not have any negative effects on plants, such as phytotoxicity.
以下に実施例をあげて本発明を説明する。 The present invention will be explained below with reference to Examples.
合成例I
N−(2−クロロイソニコチノイル)イミノジチオ炭酸
ジメチル(Ml)の合成ニ
ジメチルホルムアミド5qml中に、2−クロロイソニ
コチンアミド2,1 8 g ( 0.0 1 3 9
モル)、二硫化炭素4.1 2 g ( 0.0 5
4 2モル〕、およびヨウ化メチル6、31g(0.0
44−5モル)を加え、温度を一5°Cに保ちながら、
60%水素化ナトリウム1.22g(0.0306モル
〕を少しずつ加えた。Synthesis Example I Synthesis of dimethyl N-(2-chloroisonicotinoyl)iminodithiocarbonate (Ml) In 5 qml of dimethylformamide, 2,18 g of 2-chloroisonicotinamide (0.0139
mol), carbon disulfide 4.12 g (0.05
42 mol], and methyl iodide 6.31 g (0.0
44-5 mol) and maintaining the temperature at -5°C.
1.22 g (0.0306 mol) of 60% sodium hydride was added in portions.
加え終わった後、さらにOoCで3時間攪拌した。After the addition was completed, the mixture was further stirred at OoC for 3 hours.
反応液を水にあけ、酢酸エチルで抽出し、有機層を飽和
食塩水で洗い、硫酸すトリウムで乾燥した後、減圧濃縮
して得られた残渣をシリカゲルクロマトグラフィーにて
精製して、N−(2クロロインニコチノイル)イミノジ
チオ炭酸ジメチル2.23g(収率61.6%)を得た
。The reaction solution was poured into water, extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography to obtain N- 2.23 g (yield 61.6%) of dimethyl (2chloroinnicotinoyl)iminodithiocarbonate was obtained.
m,p,86.5〜87°C
合成例2
2−(2−クロロイソニコチノイルイミノ)−1,3−
ジチオラン(NO19)の合成ニジメチルホルムアミド
5Qml中に、2−クロロイソニコチンアミド3,13
g(0,02モル)、二硫化炭素5.9 2 g (
0.0 7 7 9モル)、および1、2−ジブロモエ
タ74.6g(0,024モル)を加え、攪拌下O0C
に保ちながら、60%水素化−18=
ナトリウム1.77 g(0,044モル)を少しずつ
加え、加え終わった後、0°Cでさらに2時間攪拌した
。反応液を水にあけ、酢酸エチルで抽出し、有機層を飽
和食塩水で洗い、硫酸ナトリウムで乾燥した後、減圧濃
縮して得られた粗結晶をジメチルホルムアミドから再結
晶して、2−(2クロロイソニコチノイルイミノ) −
1,3−ジチオラン398g(収率34.3%)を得た
。m, p, 86.5-87°C Synthesis Example 2 2-(2-chloroisonicotinolimino)-1,3-
Synthesis of dithiolane (NO19) In 5Qml of dimethylformamide, 2-chloroisonicotinamide 3,13
g (0.02 mol), carbon disulfide 5.9 2 g (
0.0779 mol) and 74.6 g (0,024 mol) of 1,2-dibromoeta were added, and the mixture was heated to O0C with stirring.
1.77 g (0,044 mol) of 60% hydrogenated-18=sodium was added little by little while maintaining the temperature, and after the addition was completed, the mixture was further stirred at 0°C for 2 hours. The reaction solution was poured into water, extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under reduced pressure, and the resulting crude crystals were recrystallized from dimethylformamide to give 2-( 2chloroisonicotinoimino) −
398 g (yield 34.3%) of 1,3-dithiolane was obtained.
m、I)、149〜151°C
合成例3
3−(2−クロロイソニコチノイル)−1(ベンジル)
−2−メチルイソチオ尿素(NO2)の合成:
エタノール20mI中に、N−(2−クロロインニコチ
ノイル)イミノジチオ炭酸ジメチル1.42g(0,0
054モル)を溶解し、ベンジルアミン0.59 g
(0,0055モル)のエタノール溶液を室温で滴下し
た。ひき続き4時間加熱還流し、溶媒を減圧留去後、水
を加え、酢酸エチルで抽出し7た。有機層を飽和食塩水
で洗い、硫酸ナトリウムで乾燥した後、減圧濃縮して得
られた残渣をシリカゲルクロマトグラフィーにて精製し
−ic、3−(2−10ロイソニコチノイル)−1(ベ
ンジル)−2−メチルイソチオ尿素1.Og(収率57
゜4%)を得た。m, I), 149-151°C Synthesis Example 3 3-(2-chloroisonicotinoyl)-1(benzyl)
-Synthesis of 2-methylisothiourea (NO2): In 20 ml of ethanol, 1.42 g of dimethyl N-(2-chloroinnicotinoyl)iminodithiocarbonate (0,0
054 mol) and 0.59 g of benzylamine
An ethanol solution of (0,0055 mol) was added dropwise at room temperature. The mixture was heated under reflux for 4 hours, the solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography to obtain -ic, 3-(2-10 leusonicotinoyl)-1(benzyl). )-2-methylisothiourea1. Og (yield 57
4%) was obtained.
m、[)、89〜90°C
合成例4
N−(2−クロロインニコチノイル)イミノチオ炭酸−
〇−アリルー8−メチル(No20)の合成ニ
ジメチルホルムアミド50m1中に、0°Cで60%水
素化ナトリウム0.77 g (0,0193モル)を
加、t だffl、N−(2−クロロインニコチノイル
)チオカルバミノ酸−〇−アリル4,48 g (0゜
0175モル)を同温度に保ちながら少しずつ加えた。m, [), 89-90°C Synthesis Example 4 N-(2-chloroinnicotinoyl)iminothiocarbonate-
Synthesis of 〇-aryl-8-methyl (No. 20) 0.77 g (0,0193 mol) of 60% sodium hydride was added to 50 ml of dimethylformamide at 0°C, and t daffl, N-(2-chloro 4.48 g (0.0175 mol) of 〇-allyl (innicotinoyl)thiocarbaminoate was added little by little while maintaining the same temperature.
30分間攪拌後、ヨウ化メチル2.73g(0,019
3モル)を滴下した。ひき続き0°Cで1時間、200
Cで2時間攪拌した抜水にあげ、酢酸エチルで抽出した
。有機層を飽和食塩水で洗い、硫酸ナトリウムで乾燥し
、減圧濃縮して得られた残渣をシリカゲルカラムクロ→
トゲラフイーにて精製して、N−(2−クロロイソニコ
チノイル)イミノチオ炭酸−〇−アリルー8−メチル1
.53g(収率32.4%)を得た。After stirring for 30 minutes, 2.73 g (0,019
3 mol) was added dropwise. Continue at 0°C for 1 hour at 200°C.
The mixture was stirred at C for 2 hours, drained, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography →
Purified with Togelafy to give N-(2-chloroisonicotinoyl)iminothiocarbonate-〇-aryl-8-methyl 1
.. 53 g (yield 32.4%) was obtained.
m、I)、61.5〜63.5°C
合成例5
2−(2−クロロインニコチノイルイミノ)−1,3−
オキサゾリジン(No16)の合成ニジオキサ730m
1中に、N−(2−クロロインニコチノイル)イミノジ
チオ炭酸ジメル2.25g (0,0086モル)、モ
ノエタノールアミン0.53 g (0,0087モル
)を加え、還流下8時間攪拌した。溶媒を減圧留去し水
を加え、酢酸エチルで抽出した。有機層を飽和食塩水で
洗い、硫酸ナトリウムで乾燥した後、減圧濃縮して得ら
れた残渣をシリカゲルクロマトグラフィーにて精製して
、2−(2−クロロイソニコチノイルイミノ)−1,3
−オキサゾリジン0.94 g (収率42.6%)を
得た。m, I), 61.5-63.5°C Synthesis Example 5 2-(2-chloroinnicotinolimino)-1,3-
Synthesis of oxazolidine (No. 16) Nidioxa 730m
2.25 g (0,0086 mol) of N-(2-chloroinnicotinoyl)iminodithiocarbonate and 0.53 g (0,0087 mol) of monoethanolamine were added to the mixture and stirred under reflux for 8 hours. The solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography to obtain 2-(2-chloroisonicotinoylimino)-1,3
-Oxazolidine 0.94 g (yield 42.6%) was obtained.
m、I)、184.5〜186°C
合成例6
2−(2−10ロイソニコチノイル)−1,3ビス(2
−シアンエチル)グアニジン(No17)の合成:
クロロホルム50m1中に、2−クロロイソニコチノイ
ルイソチアシアナート6.9.5 g (0,035モ
ル)を溶解させ、0°Cで塩素ガス(8倍モル相当)を
2時間かげて吹き込んだ。さらにooCで2時間攪拌し
た後、減圧濃縮することにより、N−(2−クロロイソ
ニコチノイル)イミドカルボニルクロリド8.7gを得
た。m, I), 184.5-186°C Synthesis Example 6 2-(2-10 leisonicotinoyl)-1,3bis(2
-Cyanethyl)guanidine (No. 17): Dissolve 6.9.5 g (0,035 mol) of 2-chloroisonicotinoyl isothiacyanate in 50 ml of chloroform, and add chlorine gas (8 times molar equivalent) was blown into the solution over a period of 2 hours. After further stirring at ooC for 2 hours, the mixture was concentrated under reduced pressure to obtain 8.7 g of N-(2-chloroisonicotinoyl)imidocarbonyl chloride.
次に、酢酸エチル20m1中に2−シアノエチルアミン
1.4 g (0,02モル)を溶解させ、200Cで
上記で得たN−(2−クロロイソニコチノイル)イミド
カルボニルクロリド1.19 g (0,005モル)
の酢酸エチル溶液を滴下し、さらに2゜0Cで30分間
攪拌した。反応液を水にあげ酢酸エチルで抽出し、有機
層を飽和食塩水で洗い、硫酸ナトリウムで乾燥した後、
減圧濃縮して得られた残渣をシリカゲルクロマトグラフ
ィーにて精製して、2−(2−クロロインニコチノイル
)−L3−ビス(2−シアンエチル)クアニジ/1.0
2g (収率67.0係)を得た。Next, 1.4 g (0.02 mol) of 2-cyanoethylamine were dissolved in 20 ml of ethyl acetate and 1.19 g of N-(2-chloroisonicotinoyl)imidocarbonyl chloride obtained above ( 0,005 mol)
An ethyl acetate solution of was added dropwise to the mixture, and the mixture was further stirred at 2°C for 30 minutes. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over sodium sulfate.
The residue obtained by concentration under reduced pressure was purified by silica gel chromatography to obtain 2-(2-chloroinnicotinoyl)-L3-bis(2-cyanethyl)quanidi/1.0
2 g (yield: 67.0) was obtained.
m、p、154〜156°C
合成例7
2−(2−クロロイソニコチノイルイミノ)1.3−オ
キサチオラン(No30)の合成:クロロホルムlQm
lとピリジンl(1ml の溶液に2−メルカプトエタ
ノール0.61g(0,0078モル)を溶解させ、0
°Cで、N−(2−クロロインニコチノイル)イミドカ
ルボニルクロリド1.7 g (0,0072モル)の
クロロホルム溶液を滴下し、さらに00Cで2時間攪拌
した。水にあけクロロホルムで抽出し、有機層を硝酸ナ
トリウムで乾燥した後、減圧濃縮して得られた残渣をシ
リカゲルクロマトグラフィーにて精製して、2−(2−
クロロイソニコチノイルイミノ)■、3−オキザチオラ
ノo、s4g(収率48.4%)を得た。m, p, 154-156°C Synthesis Example 7 Synthesis of 2-(2-chloroisonicotinolimino)1,3-oxathiolane (No30): Chloroform lQm
Dissolve 0.61 g (0,0078 mol) of 2-mercaptoethanol in a solution of 1 ml of pyridine and 1 ml of pyridine.
A chloroform solution of 1.7 g (0,0072 mol) of N-(2-chloroinnicotinoyl)imidocarbonyl chloride was added dropwise at °C, and the mixture was further stirred at 00C for 2 hours. After pouring into water and extracting with chloroform, the organic layer was dried over sodium nitrate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography.
4 g (yield: 48.4%) of chloroisonicotinoylimino), 3-oxathiolano, s was obtained.
m、p、 ゴ i (1〜 11280次に本
発明に係る一般式(1)で表わされろ化合物の代表例を
物性値ととも((第1表眞示す。m, p, go i (1 to 11280) Next, representative examples of the compound represented by the general formula (1) according to the present invention are shown together with their physical property values ((Table 1).
以下に製剤例を示すが、農薬補助剤の種類および混合比
率はこれらのみに限定されることなく、広い範囲で使用
可能である。なお1部」とあるのは重量部を意味する。Formulation examples are shown below, but the types and mixing ratios of agricultural chemical adjuvants are not limited to these, and can be used in a wide range. Note that "1 part" means parts by weight.
製剤例1 粉 剤
化合物No、7.2部およびクレー98部を混合粉砕し
、粉剤とする。Formulation Example 1 Powder 7.2 parts of Compound No. and 98 parts of clay are mixed and ground to form a powder.
製剤例2. 水和剤
化合物No、10.20部とカオリ775部と高級アル
コール硫酸ナトリウム3部およびリグニンスルホン酸ナ
トリウム2部とを混合粉砕し水和剤とする。Formulation example 2. Wettable powder compound No. 10.20 parts, 775 parts of Kaori, 3 parts of higher alcohol sodium sulfate, and 2 parts of sodium ligninsulfonate are mixed and ground to obtain a wettable powder.
製剤例3 粒 剤
微粉砕した化合物No、19.8部ベントナイト60部
、タルク30部および崩壊剤2部を混合した後、水18
部を加え、均等に湿潤させ、次に射出成形機を通して押
し出し、造粒し、整粒機で整粒した後、乾燥し粒径Q、
5 rrm〜1mmの粒剤とする。Formulation Example 3 Granules After mixing 19.8 parts of finely pulverized compound No., 60 parts of bentonite, 30 parts of talc, and 2 parts of disintegrant, 18 parts of water was added.
After adding 100% of the total amount of water and moistening it evenly, extruding it through an injection molding machine, granulating it, sizing it with a sizing machine, and drying it to obtain a particle size of Q,
5 rrm to 1 mm granules.
製剤例46 微粒剤
化合物No、31.5部をポリビニルアルコール1部お
よびクレー14部を均一に混合粉砕し、濃厚粉状物とな
す。別に74〜105μの非吸収性の鉱物質粗粉80部
を適当な混合機に入れ回転しながら水15部を加え湿ら
せ、上記濃厚粉状物を添加し被覆せしめ乾燥し微粒剤と
する。Formulation Example 46 31.5 parts of fine granule compound No. are uniformly mixed and pulverized with 1 part of polyvinyl alcohol and 14 parts of clay to form a thick powder. Separately, 80 parts of non-absorbable mineral coarse powder of 74 to 105 μm is placed in a suitable mixer, and 15 parts of water is added while rotating to moisten it, and the above-mentioned thick powder is added, coated, and dried to form fine granules.
製剤例5. 乳 剤
化合物No、5、30部をキシレン52部に溶解し、こ
れにアルキルフェノールエチレンオキシド縮合物とアル
キルベンゼンスルホン酸カルシウムの混合物(8:2)
18部を混合溶解して乳剤とする。Formulation example 5. Emulsion compound No. 5, 30 parts was dissolved in 52 parts of xylene, and a mixture of alkylphenol ethylene oxide condensate and calcium alkylbenzenesulfonate (8:2) was dissolved therein.
Mix and dissolve 18 parts to make an emulsion.
次に本発明の化合物が各種の農園芸用作物病害に対し、
すぐれた防除効果を有していることを実験例により説明
する。Next, the compound of the present invention can be used against various agricultural and horticultural crop diseases.
The fact that it has an excellent pest control effect will be explained using experimental examples.
実験例1. イネいもち病防除試験(土壌施用)たて1
1cm、よこ5 cm、高さlQcmのプラスチック類
のポットに2週間イネ(品種:埼玉もち10号)を生育
させ、このイネに製剤例3の方法で作成した本発明化合
物を有効成分とす−30=
る粒剤を所定量土壌施用し、7日後にイ坏いもち病菌(
Pyricularia oryzae )の胞子懸濁
液を噴霧接種し、23°Cの温室に2日間保った後、温
室内で発病させ、接種10日後に発病程度を調査し防除
価を算出した。結果は第2表の通りである。なお対照剤
としてIBP粒剤(有効成分:S−ペンジルジイソプロ
ピルホスホロチオレト)を用いた。Experimental example 1. Rice blast control test (soil application) fresh 1
Rice (variety: Saitama Mochi No. 10) was grown for two weeks in a plastic pot measuring 1 cm, width 5 cm, and height 1 Q cm, and the compound of the present invention prepared by the method of Formulation Example 3 was added to the rice as an active ingredient. 30 = Apply a predetermined amount of granules to the soil, and after 7 days, the blast fungus (
A spore suspension of Pyricularia oryzae) was spray inoculated, kept in a greenhouse at 23°C for 2 days, and then allowed to develop in the greenhouse. Ten days after inoculation, the degree of disease onset was investigated and the control value was calculated. The results are shown in Table 2. As a control agent, IBP granules (active ingredient: S-penzyl diisopropyl phosphorothiolet) were used.
第2表 イ ネいもち病防除試験(土壌施用) 0:病斑が全く認められない。Table 2 stomach Blast control test (soil application) 0: No lesions observed at all.
1:病斑がわずかに認められろ。1: Slight lesions are observed.
2:病斑が多数認められる。2: Many lesions are observed.
4:枯死葉が多く認められる。4: Many dead leaves are observed.
5:枯死葉がきわめて多く認めら れる。5: Very many dead leaves were observed. It will be done.
実験例2 イネいもち病防除試1験(茎葉散布)たて]
、 l (:rn 、よこ5 cm 、高さ10 cm
のプラスチック製のポットに2週間、イネ(品種:埼玉
もち10号)を生育させ、このイネ1に製剤例2の方法
で作成した本発明化合物を有効成分とする水相剤を希釈
して得た所定濃度の薬液を茎葉散布した。風乾後、イネ
いもち病菌(Pyricularia(財)ヨ)の胞子
懸濁液を噴霧接種し、25°Cの温室に1日間保った後
、温室内で発病させ、接種10日後に発病程度を調査し
、防除価を算出した。結果は第3表の通りである。なお
対照薬剤としてIBP乳剤(有効成分:S−ベノジルジ
イソフロピルホスホロチオレート)を用いた。Experimental Example 2 Rice blast control test 1 (spraying on foliage)]
, l (:rn, width 5 cm, height 10 cm
Rice (variety: Saitama Mochi No. 10) was grown in a plastic pot for two weeks, and the aqueous phase agent prepared by the method of Formulation Example 2 containing the compound of the present invention as an active ingredient was diluted into the rice. A chemical solution with a predetermined concentration was sprayed on the foliage. After air-drying, the rice was inoculated by spraying with a spore suspension of the rice blast fungus (Pyricularia (Incorporated)), kept in a greenhouse at 25°C for 1 day, allowed to develop in the greenhouse, and 10 days after inoculation, the degree of disease onset was investigated. , the control value was calculated. The results are shown in Table 3. In addition, IBP emulsion (active ingredient: S-benozyl diisofuropyl phosphorothiolate) was used as a control drug.
0:病斑が全く認められない。0: No lesions observed at all.
1:病斑がわずかに認められる。1: Slight lesions are observed.
2:病斑が多数認められる。2: Many lesions are observed.
発病程度 3:病斑きわめて多く枯死葉がわずかに認め
られる。Disease severity: 3: Very many lesions and a few dead leaves are observed.
4:枯死葉が多く認められる。4: Many dead leaves are observed.
5:枯死葉がきわめて多く認めら れろ。5: Very many dead leaves were observed. Let's go.
第3表
イ
ネいもち病防除試験(茎葉散布)
実験例3 イネ白葉枯病防除試験(土壌施用)たて15
cm、よこ5cm、高さ]、 Ocmのプラスチック
ポットに1ケ月半、イネ(品種:ムサシコガネ)を生育
させた。このイネに製剤例3の方法で製剤した本発明化
合物の粒剤を所定量土壌施用し、2日後イネの葉ICイ
ネ白葉枯病菌(Xanthomonas campes
lris p、v、orytae ) を剪7葉接種
し、30°Cの温室に24時間保って感染させ、引き続
き温室内で発病させた。接種21日後に病斑長を調査し
た。結果は第4表の通りである。Table 3 Rice blast control test (sprayed on foliage) Experimental example 3 Rice blast control test (soil application) Fresh 15
Rice (variety: Musashikogane) was grown for one and a half months in a plastic pot measuring [cm, width 5 cm, height], Ocm. A predetermined amount of the granules of the compound of the present invention prepared by the method of Formulation Example 3 was applied to the soil of this rice, and two days later, the rice leaves were infected with IC rice leaf blight (Xanthomonas campes).
lris p, v, orytae) was inoculated with seven pruned leaves, kept in a greenhouse at 30°C for 24 hours to infect, and then allowed to develop disease in the greenhouse. Lesion length was investigated 21 days after inoculation. The results are shown in Table 4.
なお対照薬剤としてプロペナゾール粒剤(有効成分=1
,2−ベンズイソチアゾール−3−オン−1,1−ジオ
キシド)を用いた。As a control drug, propenazole granules (active ingredient = 1
, 2-benzisothiazol-3-one-1,1-dioxide).
第4表 イネ白葉枯病(土壌施用)Table 4 Rice leaf blight (soil application)
Claims (2)
基(ただし、XおよびYは同時に酸素原子であることは
ない)を示し、R^1およびR^2は、それぞれ独立に
、低級アルキル基、低級シアノアルキル基、アリル基、
プロパルギル基、フェニル基または2−ピリジル基を示
す。またR^1とR^2は、▲数式、化学式、表等があ
ります▼で結合し、環状構造をとることもでき、ここで
nは2または3を示し、または▲数式、化学式、表等が
あります▼で結合し、 環状構造をとることもでき、ここでZは水素原子、また
は塩素原子を示し、lとmは0または1であり、かつl
+m=0または1を示す。〕で表わされるN−(2−ク
ロロイソニコチノイル)イミノ誘導体。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) [In the formula, X and Y are each independently an oxygen atom, a sulfur atom, an imino group, or a methylimino group (however, X and Y are R^1 and R^2 each independently represent a lower alkyl group, a lower cyanoalkyl group, an allyl group,
It represents a propargyl group, a phenyl group or a 2-pyridyl group. Also, R^1 and R^2 can be combined with ▲ to form a cyclic structure, where n represents 2 or 3, or ▲ to form a cyclic structure. can be bonded with ▼ to form a cyclic structure, where Z represents a hydrogen atom or a chlorine atom, l and m are 0 or 1, and l
+m=0 or 1. ] N-(2-chloroisonicotinoyl)imino derivative.
味する。〕で表わされるN−(2−クロロイソニコチノ
イル)イミノ誘導体を有効成分とする農園芸用殺菌剤。(2) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, X, Y, R^1 and R^2 have the same meanings as above. ] An agricultural and horticultural fungicide containing an N-(2-chloroisonicotinoyl)imino derivative represented by the following as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4860889A JPH02229164A (en) | 1989-03-02 | 1989-03-02 | N-(2-chloroisonicotinoyl)imino derivative or fungicide for agricultural and horticultural purposes containing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4860889A JPH02229164A (en) | 1989-03-02 | 1989-03-02 | N-(2-chloroisonicotinoyl)imino derivative or fungicide for agricultural and horticultural purposes containing the same |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH02229164A true JPH02229164A (en) | 1990-09-11 |
Family
ID=12808124
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4860889A Pending JPH02229164A (en) | 1989-03-02 | 1989-03-02 | N-(2-chloroisonicotinoyl)imino derivative or fungicide for agricultural and horticultural purposes containing the same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH02229164A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008108448A1 (en) | 2007-03-07 | 2008-09-12 | Nissan Chemical Industries, Ltd. | Isoxazoline-substituted benzamide compound and pest control agent |
CN103772376A (en) * | 2012-10-24 | 2014-05-07 | 中国医学科学院医药生物技术研究所 | Substituted benzo-1,3-miscellaneous azole compound and preparation method and application thereof |
CN116655617A (en) * | 2023-05-31 | 2023-08-29 | 中国科学院昆明植物研究所 | 2-aminobenzoxazole derivative, preparation method and application thereof in resisting rice blast bacteria |
-
1989
- 1989-03-02 JP JP4860889A patent/JPH02229164A/en active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008108448A1 (en) | 2007-03-07 | 2008-09-12 | Nissan Chemical Industries, Ltd. | Isoxazoline-substituted benzamide compound and pest control agent |
CN103772376A (en) * | 2012-10-24 | 2014-05-07 | 中国医学科学院医药生物技术研究所 | Substituted benzo-1,3-miscellaneous azole compound and preparation method and application thereof |
CN116655617A (en) * | 2023-05-31 | 2023-08-29 | 中国科学院昆明植物研究所 | 2-aminobenzoxazole derivative, preparation method and application thereof in resisting rice blast bacteria |
CN116655617B (en) * | 2023-05-31 | 2024-04-19 | 中国科学院昆明植物研究所 | 2-Aminobenzoxazole derivative, preparation method and application thereof in resisting rice blast bacteria |
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