CN104520273A - 2-氨基烟酸酯衍生物及以其为有效成分的灭菌剂 - Google Patents
2-氨基烟酸酯衍生物及以其为有效成分的灭菌剂 Download PDFInfo
- Publication number
- CN104520273A CN104520273A CN201380035233.9A CN201380035233A CN104520273A CN 104520273 A CN104520273 A CN 104520273A CN 201380035233 A CN201380035233 A CN 201380035233A CN 104520273 A CN104520273 A CN 104520273A
- Authority
- CN
- China
- Prior art keywords
- group
- compound
- patent documentation
- alkyl
- hydrogen atom
- 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.)
- Granted
Links
- -1 2-aminonicotinic acid ester Chemical class 0.000 title claims abstract description 85
- 239000004480 active ingredient Substances 0.000 title abstract 3
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 2
- 239000003899 bactericide agent Substances 0.000 title abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 239000000470 constituent Substances 0.000 claims description 17
- 239000000645 desinfectant Substances 0.000 claims description 17
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 86
- 201000010099 disease Diseases 0.000 description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241000221785 Erysiphales Species 0.000 description 9
- 206010027146 Melanoderma Diseases 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 230000001580 bacterial effect Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- KPIVDNYJNOPGBE-UHFFFAOYSA-N 2-aminonicotinic acid Chemical compound NC1=NC=CC=C1C(O)=O KPIVDNYJNOPGBE-UHFFFAOYSA-N 0.000 description 7
- 240000008067 Cucumis sativus Species 0.000 description 7
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 7
- 206010039509 Scab Diseases 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010413 gardening Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- 241000193738 Bacillus anthracis Species 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 244000052616 bacterial pathogen Species 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 230000001954 sterilising effect Effects 0.000 description 5
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 4
- 241000207199 Citrus Species 0.000 description 4
- 241001672694 Citrus reticulata Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241000232299 Ralstonia Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000009754 Vitis X bourquina Nutrition 0.000 description 4
- 235000012333 Vitis X labruscana Nutrition 0.000 description 4
- 240000006365 Vitis vinifera Species 0.000 description 4
- 235000014787 Vitis vinifera Nutrition 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 235000020971 citrus fruits Nutrition 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 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 4
- 239000002002 slurry Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000004546 suspension concentrate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 244000291564 Allium cepa Species 0.000 description 3
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000896238 Oidium Species 0.000 description 3
- 208000008469 Peptic Ulcer Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000220324 Pyrus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 241001122767 Theaceae Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000589649 Xanthomonas campestris pv. campestris Species 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000213004 Alternaria solani Species 0.000 description 2
- 244000144730 Amygdalus persica Species 0.000 description 2
- 240000007087 Apium graveolens Species 0.000 description 2
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 2
- 235000010591 Appio Nutrition 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000007516 Chrysanthemum Nutrition 0.000 description 2
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 2
- 241001123536 Colletotrichum acutatum Species 0.000 description 2
- 244000241257 Cucumis melo Species 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 101100117236 Drosophila melanogaster speck gene Proteins 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 235000016623 Fragaria vesca Nutrition 0.000 description 2
- 240000009088 Fragaria x ananassa Species 0.000 description 2
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 244000017020 Ipomoea batatas Species 0.000 description 2
- 235000002678 Ipomoea batatas Nutrition 0.000 description 2
- 240000003978 Ipomoea coccinea Species 0.000 description 2
- 240000001585 Limonium sinuatum Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- 241001518836 Monilinia fructigena Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 241000237502 Ostreidae Species 0.000 description 2
- 241000588702 Pectobacterium carotovorum subsp. carotovorum Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 241000233645 Phytophthora nicotianae Species 0.000 description 2
- 240000004713 Pisum sativum Species 0.000 description 2
- 235000010582 Pisum sativum Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- 241000589623 Pseudomonas syringae pv. syringae Species 0.000 description 2
- 241001092459 Rubus Species 0.000 description 2
- 235000017848 Rubus fruticosus Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- 244000061458 Solanum melongena Species 0.000 description 2
- 241000187181 Streptomyces scabiei Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000035613 defoliation Effects 0.000 description 2
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 235000020636 oyster Nutrition 0.000 description 2
- 235000021017 pears Nutrition 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 238000010010 raising Methods 0.000 description 2
- 210000000582 semen Anatomy 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000003934 Abelmoschus esculentus Nutrition 0.000 description 1
- 240000004507 Abelmoschus esculentus Species 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 241001600124 Acidovorax avenae Species 0.000 description 1
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 1
- 244000298697 Actinidia deliciosa Species 0.000 description 1
- 241000589155 Agrobacterium tumefaciens Species 0.000 description 1
- 241000589176 Agrobacterium vitis Species 0.000 description 1
- 241000212251 Alternaria dauci Species 0.000 description 1
- 241000266416 Alternaria japonica Species 0.000 description 1
- 241000352690 Alternaria kikuchiana Species 0.000 description 1
- 241000323752 Alternaria longipes Species 0.000 description 1
- 241000412366 Alternaria mali Species 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 240000001436 Antirrhinum majus Species 0.000 description 1
- 241001444083 Aphanomyces Species 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 241001530056 Athelia rolfsii Species 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 208000019775 Back disease Diseases 0.000 description 1
- 235000011274 Benincasa cerifera Nutrition 0.000 description 1
- 244000036905 Benincasa cerifera Species 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- 241001450781 Bipolaris oryzae Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000555706 Botryosphaeria dothidea Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 240000008100 Brassica rapa Species 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 1
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- 241000134107 Burkholderia plantarii Species 0.000 description 1
- 240000001548 Camellia japonica Species 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 240000008384 Capsicum annuum var. annuum Species 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 235000009467 Carica papaya Nutrition 0.000 description 1
- 240000006432 Carica papaya Species 0.000 description 1
- 244000281594 Cassia siamea Species 0.000 description 1
- 241001674939 Caulanthus Species 0.000 description 1
- 241000530549 Cercospora beticola Species 0.000 description 1
- 241001658057 Cercospora kikuchii Species 0.000 description 1
- 244000241235 Citrullus lanatus Species 0.000 description 1
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 1
- 244000183685 Citrus aurantium Species 0.000 description 1
- 235000007716 Citrus aurantium Nutrition 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 235000001759 Citrus maxima Nutrition 0.000 description 1
- 244000276331 Citrus maxima Species 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241000555678 Citrus unshiu Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 241000222290 Cladosporium Species 0.000 description 1
- 241001464977 Clavibacter michiganensis subsp. michiganensis Species 0.000 description 1
- 241000037488 Coccoloba pubescens Species 0.000 description 1
- 244000077995 Coix lacryma jobi Species 0.000 description 1
- 235000007354 Coix lacryma jobi Nutrition 0.000 description 1
- 241000222199 Colletotrichum Species 0.000 description 1
- 241001133184 Colletotrichum agaves Species 0.000 description 1
- 241000152100 Colletotrichum horii Species 0.000 description 1
- 241000222235 Colletotrichum orbiculare Species 0.000 description 1
- 241000998302 Colletotrichum tabaci Species 0.000 description 1
- 235000006481 Colocasia esculenta Nutrition 0.000 description 1
- 244000205754 Colocasia esculenta Species 0.000 description 1
- 241001503991 Consolida Species 0.000 description 1
- 241000544061 Cuculus canorus Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 235000009847 Cucumis melo var cantalupensis Nutrition 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
- 240000006497 Dianthus caryophyllus Species 0.000 description 1
- 241001645342 Diaporthe citri Species 0.000 description 1
- 241000382787 Diaporthe sojae Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000663351 Diplocarpon rosae Species 0.000 description 1
- 241000125117 Elsinoe Species 0.000 description 1
- 241001568757 Elsinoe glycines Species 0.000 description 1
- 241001564064 Elsinoe theae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000009008 Eriobotrya japonica Nutrition 0.000 description 1
- 244000061508 Eriobotrya japonica Species 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- 241001489205 Erysiphe pisi Species 0.000 description 1
- 240000002395 Euphorbia pulcherrima Species 0.000 description 1
- 241001411323 Exobasidium reticulatum Species 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 241001096509 Gazania linearis Species 0.000 description 1
- 241000246500 Gentianella aspera Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 241001194823 Gymnosporangium asiaticum Species 0.000 description 1
- 241001540851 Gymnosporangium yamadae Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 206010019617 Henoch-Schonlein purpura Diseases 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 235000014486 Hydrangea macrophylla Nutrition 0.000 description 1
- 244000267823 Hydrangea macrophylla Species 0.000 description 1
- 208000031814 IgA Vasculitis Diseases 0.000 description 1
- 241000032989 Ipomoea lacunosa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 240000006568 Lathyrus odoratus Species 0.000 description 1
- 241000896221 Leveillula taurica Species 0.000 description 1
- 241001635593 Lisianthius Species 0.000 description 1
- 235000009814 Luffa aegyptiaca Nutrition 0.000 description 1
- 244000302544 Luffa aegyptiaca Species 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000009811 Momordica charantia Nutrition 0.000 description 1
- 235000009812 Momordica cochinchinensis Nutrition 0.000 description 1
- 240000001740 Momordica dioica Species 0.000 description 1
- 235000018365 Momordica dioica Nutrition 0.000 description 1
- 241001518729 Monilinia Species 0.000 description 1
- 241001518731 Monilinia fructicola Species 0.000 description 1
- 241001363493 Monilinia mali Species 0.000 description 1
- 241001459558 Monographella nivalis Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241000083073 Neopseudocercosporella capsellae Species 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 241001329956 Nothopassalora personata Species 0.000 description 1
- 241001668536 Oculimacula yallundae Species 0.000 description 1
- 241000282373 Panthera pardus Species 0.000 description 1
- 241000736122 Parastagonospora nodorum Species 0.000 description 1
- 241000315044 Passalora arachidicola Species 0.000 description 1
- 241000222291 Passalora fulva Species 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 241000594335 Pavetta Species 0.000 description 1
- 241001148142 Pectobacterium atrosepticum Species 0.000 description 1
- 241001507673 Penicillium digitatum Species 0.000 description 1
- 241000582441 Peronospora tabacina Species 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- 240000007377 Petunia x hybrida Species 0.000 description 1
- 241001098206 Phakopsora ampelopsidis Species 0.000 description 1
- 241001557902 Phomopsis sp. Species 0.000 description 1
- 241000257732 Phomopsis vexans Species 0.000 description 1
- 241000210649 Phyllosticta ampelicida Species 0.000 description 1
- 241000555714 Phyllosticta citricarpa Species 0.000 description 1
- 241001270527 Phyllosticta citrullina Species 0.000 description 1
- 241000233631 Phytophthora citrophthora Species 0.000 description 1
- 241000233629 Phytophthora parasitica Species 0.000 description 1
- 241000031556 Phytophthora sp. Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241000317981 Podosphaera fuliginea Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 241001294742 Podosphaera macularis Species 0.000 description 1
- 241000896203 Podosphaera pannosa Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 235000009827 Prunus armeniaca Nutrition 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 244000141698 Prunus lannesiana Species 0.000 description 1
- 235000006029 Prunus persica var nucipersica Nutrition 0.000 description 1
- 244000017714 Prunus persica var. nucipersica Species 0.000 description 1
- 235000014001 Prunus serrulata Nutrition 0.000 description 1
- 241000301598 Pseudocercospora kaki Species 0.000 description 1
- 241000521936 Pseudomonas amygdali pv. lachrymans Species 0.000 description 1
- 241000218936 Pseudomonas corrugata Species 0.000 description 1
- 241000490004 Pseudomonas fuscovaginae Species 0.000 description 1
- 241000394642 Pseudomonas marginalis pv. marginalis Species 0.000 description 1
- 241000589612 Pseudomonas savastanoi pv. glycinea Species 0.000 description 1
- 241000589613 Pseudomonas savastanoi pv. phaseolicola Species 0.000 description 1
- 241001487783 Pseudomonas syringae pv. theae Species 0.000 description 1
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 1
- 241001246058 Puccinia allii Species 0.000 description 1
- 241000221301 Puccinia graminis Species 0.000 description 1
- 241001123559 Puccinia hordei Species 0.000 description 1
- 241000312975 Puccinia horiana Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 241001123583 Puccinia striiformis Species 0.000 description 1
- 241000520648 Pyrenophora teres Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 241001385948 Pythium sp. Species 0.000 description 1
- 241000589771 Ralstonia solanacearum Species 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 241000022649 Rhizobacter dauci Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 241001515790 Rhynchosporium secalis Species 0.000 description 1
- 244000178231 Rosmarinus officinalis Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 244000070968 Saintpaulia ionantha Species 0.000 description 1
- 235000002493 Salix babylonica Nutrition 0.000 description 1
- 244000020191 Salix babylonica Species 0.000 description 1
- 235000005794 Salvia japonica Nutrition 0.000 description 1
- 244000295490 Salvia japonica Species 0.000 description 1
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
- 241001558929 Sclerotium <basidiomycota> Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 241000336765 Septoria chrysanthemella Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 235000009184 Spondias indica Nutrition 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
- 241000142909 Streptomyces acidiscabies Species 0.000 description 1
- 241001655322 Streptomycetales Species 0.000 description 1
- 229930182692 Strobilurin Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 241000775848 Syringa oblata Species 0.000 description 1
- 241000722093 Tilletia caries Species 0.000 description 1
- 241000051572 Typhula sp. Species 0.000 description 1
- 241000007070 Ustilago nuda Species 0.000 description 1
- 241000233791 Ustilago tritici Species 0.000 description 1
- 241001512566 Valsa mali Species 0.000 description 1
- 241001669640 Venturia carpophila Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241001669638 Venturia nashicola Species 0.000 description 1
- 241001006642 Venturia pyrina Species 0.000 description 1
- 235000018718 Verbena officinalis Nutrition 0.000 description 1
- 240000001519 Verbena officinalis Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 235000010726 Vigna sinensis Nutrition 0.000 description 1
- 235000011453 Vigna umbellata Nutrition 0.000 description 1
- 240000001417 Vigna umbellata Species 0.000 description 1
- 244000042314 Vigna unguiculata Species 0.000 description 1
- 241000985670 Xanthomonas arboricola pv. pruni Species 0.000 description 1
- 241000589655 Xanthomonas citri Species 0.000 description 1
- 241001517731 Xanthomonas citri pv. glycines Species 0.000 description 1
- 241000231754 Xanthomonas fragariae Species 0.000 description 1
- 241000907138 Xanthomonas oryzae pv. oryzae Species 0.000 description 1
- 241000194062 Xanthomonas phaseoli Species 0.000 description 1
- 241000567011 Xanthomonas theicola Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- 241001360088 Zymoseptoria tritici Species 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000003857 carboxamides 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
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000006011 chloroethoxy group Chemical group 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000018597 common camellia Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000005822 corn Nutrition 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
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 150000008056 dicarboxyimides Chemical class 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 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
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- JUMYIBMBTDDLNG-OJERSXHUSA-N hydron;methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate;chloride Chemical compound Cl.C([C@@H]1[C@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 JUMYIBMBTDDLNG-OJERSXHUSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 208000015446 immunoglobulin a vasculitis Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940094506 lauryl betaine Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940099204 ritalin Drugs 0.000 description 1
- 235000015639 rosmarinus officinalis Nutrition 0.000 description 1
- 102200025554 rs730882050 Human genes 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 244000029478 serpent melon Species 0.000 description 1
- 235000008933 serpent melon Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000003046 sporozoite Anatomy 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 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
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000000051 wattle Anatomy 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明提供一种以2-氨基烟酸酯衍生物为有效成分的灭菌剂。本发明的有效成分由以下的式[I]表示。(式中,R1表示氢原子或C1~C4的烷基,R2表示氢原子或C1~C4的烷基,R1和R2可以相互键合而形成亚烷基链,R3表示氢原子、C1~C4的烷基,R4表示氢原子、氰基或C1~C4的烷基,R5及R6相互独立地表示氢原子、卤原子、C1~C4的烷基、C1~C4的烷氧基、C1~C4的烷基硫基、C1~C4的烷基亚硫酰基、C1~C4的烷基磺酰基、硝基、氰基、C1~C4的卤烷基、C1~C4的卤烷氧基或C1~C4的卤烷基硫基,A及B相互独立地表示次甲基(CH)或氮原子)。
Description
技术领域
本发明涉及一种2-氨基烟酸酯衍生物及以其为有效成分含有的灭菌剂。
背景技术
在农业和园艺领域中,开发了以各种病原菌的防除为目的的各种灭菌剂,供于实用。
但是,目前通用的农药未必可以说满足其效果及光谱、残效性等,进而施用次数和施用药量的降低等要求。此外,对目前通用的农药的抵抗性发达的病原菌的出现也成为问题。例如,在蔬菜和果树、花卉、茶、糊米类及水稻等栽培中,对例如三唑类、咪唑类、嘧啶类、苯并咪唑类、二羧基酰亚胺类、苯基酰胺类、嗜球果伞素类等各种类型的灭菌剂的抵抗性发达的各种病原菌在各地出现,这些抵抗性病原菌的防除每年都很困难。因此,经常期望相对于对目前通用的农业和园艺用灭菌剂的抵抗性发达的各种病原菌也以低药量显示充分的防除效果、而且对环境的不良影响小的、新型的农药的出现。
提出了各种用于适应于这些要求的新的灭菌剂,但未必适应于上述要求。
在专利文献1中公开有含有具有灭菌活性的以下结构的甲酰胺衍生物。但是,专利文献1中记载的化合物在吡啶环的3位上具有甲酰胺键,并不具有酯键。
专利文献2中,将在吡啶环的2位上具有氨基的以下酯衍生物作为反应中间体(265页实施例35化合物编号757)公开。但是,该化合物为具有甲氧基的化合物,并不具有苯氧基。另外,该化合物归根结底只不过作为专利文献2的医药活性化合物的制造中间体公开,专利文献2中对灭菌活性完全没有记载。
专利文献3~6中,作为具体合成的化合物,对如下所述的在吡啶环的2-位上不具有氨基的酯衍生物公开。作为其代表例,可例示以下的化合物。公开有这些化合物具有杀虫活性或除草活性,但具有灭菌活性则完全没有报道。
专利文献3公开有以下的化合物(43页化合物编号1.59)。但是,专利文献3没有公开与作为杀虫剂的用途有关、在吡啶环的2位上具有氨基的化合物。
专利文献4公开有以下的化合物(33页化合物270及271)。但是,专利文献4没有公开与作为杀虫剂的用途有关、在吡啶环的2位上具有氨基的化合物。
专利文献5公开有以下的化合物(78页的化合物编号1.3717)。但是,专利文献5没有公开与作为除草剂的用途有关、在吡啶环的2位上具有氨基的化合物。
专利文献6公开有以下的化合物(42页的化合物编号229)。但是,专利文献6没有公开与作为除草剂的用途有关、在吡啶环的2位上具有氨基的化合物。
另外,专利文献7或专利文献8中,作为具有灭菌活性的具体的化合物,公开有以下的化合物。
具体而言,专利文献7公开有以下的化合物(50页的化合物编号48)。但是,专利文献7中没有公开在吡啶环的2位上具有氨基的化合物。
另外,专利文献8公开有以下的化合物(40页的化合物编号22)。但是,专利文献8没有公开在吡啶环的2位上具有氨基的化合物。
另一方面,专利文献9~14具体地公开有具有医药活性的以下的化合物。详述为,专利文献9公开有以下的化合物(42页的实施例186)。但是,专利文献9没有公开在吡啶环的2位上具有氨基的化合物。另外,专利文献9的化合物只不过作为医药活性物质公开。
另外,专利文献10具体公开有以下的化合物(32页工序3的反应式右侧的化合物)。但是,该化合物只不过作为反应中间体被公开,另外专利文献10没有公开在吡啶环的2位上具有氨基的化合物。
专利文献11公开有以下的化合物作为丙基-3-烟酰(17页)。但是,专利文献11没有公开在吡啶环的2位上具有氨基的化合物。另外,专利文献11的化合物只不过作为医药活性物质公开。
专利文献12公开有以下的化合物(51页的E工序1)。但是,专利文献11仅将该化合物作为中间体公开,没有公开在吡啶环的2位上具有氨基的化合物。另外,专利文献11的化合物只不过作为医药活性物质公开。
专利文献13公开有以下的化合物(56页(I-17b))。但是,专利文献13没有公开在吡啶环的2位上具有氨基的化合物。另外,专利文献13的化合物只不过作为医药活性物质公开。
专利文献13公开有以下的化合物(93页、合成方案)。但是,专利文献13中,该化合物仅作为中间体公开,没有公开在吡啶环的2位上具有氨基的化合物。另外,专利文献13的化合物只不过作为医药活性物质公开。
非专利文献1涉及一种作为查格斯氏病的治疗剂使用的医药活性化合物。非专利文献1就具有苯氧基苄氧基骨架的医药活性化合物进行了公开。但是,关于在该骨架上插入有2-氨基烟酸的化合物则完全没有公开。
现有技术文献
专利文献
专利文献1:日本特开2010-083861号公报
专利文献2:WO2008-082490号小册子
专利文献3:WO2004-056735号小册子
专利文献4:WO2002-002515号小册子
专利文献5:WO2000-015615号小册子
专利文献6:日本特开2004-051628号公报
专利文献7:WO1994-029267号小册子
专利文献8:WO1998-033772号小册子
专利文献9:EP1995-650961号小册子
专利文献10:WO1998-057946号小册子
专利文献11:WO2003-101980号小册子
专利文献12:WO2007-133561号小册子
专利文献13:WO2010-029461号小册子
专利文献14:WO2011-083304号小册子
非专利文献
非专利文献1:Journal of Medicinal Chemistry,43卷,1826页(2000)
发明内容
发明要解决的课题
本发明提供一种对各种菌类的防除有用的新的物质,特别提供一种相对于现有的灭菌剂显示抵抗性、同时相对于各种菌类也显示高的防除效果、进而以低药量产生效果、因此残留毒性和环境污染等问题得到减轻的安全性高的物质。
解决课题的技术方案
本发明人等为了解决上述的课题进行了潜心研究,结果发现,下式规定的2-氨基烟酸酯衍生物为具有可以适应于上述要求的特性的化合物,直至完成了本发明。
即,本发明涉及一种2-氨基烟酸酯衍生物(以下,也称为“本发明的化合物”)及含有其作为有效成分的灭菌剂,所述2-氨基烟酸酯衍生物用下式[I]表示:
(式中,R1表示氢原子或C1~C4的烷基,
R2表示氢原子、C1~C4的烷基,或R1和R2相互键合,表示
或
R3表示氢原子、C1~C4的烷基,
R4表示氢原子、氰基或C1~C4的烷基,
R5及R6相互独立地表示氢原子、卤原子、C1~C4的烷基、C1~C4的烷氧基、C1~C4的烷基硫基、C1~C4的烷基亚硫酰基、C1~C4的烷基磺酰基、硝基、氰基、C1~C4的卤烷基、C1~C4的卤烷氧基或C1~C4的卤烷基硫基,
A及B相互独立地表示次甲基(CH)或氮原子。)
发明效果
本发明的化合物相对于各种菌类显示优异的效果。
具体实施方式
以下,对本发明详细地说明。
式[I]表示的本发明的化合物中,作为R1、R2、R3、R5及R6表示的C1~C4的烷基,可列举例如:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基等。作为R5及R6表示的卤原子,可列举例如:氟原子、氯原子、溴原子、碘原子。
作为R5及R6表示的C1~C4的烷氧基,可列举例如:甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基。
作为R5及R6表示的C1~C4的烷基硫基,可列举例如:甲基硫基、乙基硫基、正丙基硫基、异丙基硫基、正丁基硫基、异丁基硫基、仲丁基硫基、叔丁基硫基。
作为R5及R6表示的C1~C4的烷基亚硫酰基,可列举例如:甲基亚硫酰基、乙基亚硫酰基、正丙基亚硫酰基、异丙基亚硫酰基、正丁基亚硫酰基、异丁基亚硫酰基、仲丁基亚硫酰基、叔丁基亚硫酰基。
作为R5及R6表示的C1~C4的烷基磺酰基,可列举例如:甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基。
作为R5及R6表示的C1~C4的卤烷基,可列举例如:单氟甲基、二氟甲基、三氟甲基、单氯甲基、二氯甲基、三氯甲基、单溴甲基、二溴甲基、三溴甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2,2-二氟乙基、1-氯乙基、2-氯乙基、2,2,-二氯乙基、2,2,2-三氯乙基、1-溴乙基、2-溴乙基、2,2-二溴乙基、2,2,2-三溴乙基、2-碘乙基、五氟乙基、3-氟丙基、3-氯丙基、3-溴丙基、1,3-二氟-2-丙基、3,3,3-三氟丙基、1,3-二氯-2-丙基、1,1,1-三氟-2-丙基、1-氯-3-氟-2-丙基、1,1,1,3,3,3-六氟-2-丙基、1,1,1,3,3,3-六氟-2-氯-2-丙基、2,2,3,3,3-五氟丙基、七氟异丙基、七氟-正丙基、4-氟丁基、4,4,4-三氟丁基、九氟-正丁基、九氟-2-丁基。
作为R5及R6表示的C1~C4的卤烷氧基,可列举例如:单氟甲氧基、二氟甲氧基、三氟甲氧基、单氯甲氧基、二氯甲氧基、三氯甲氧基、单溴甲氧基、二溴甲氧基、三溴甲氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2,2-二氟乙氧基、1-氯乙氧基、2-氯乙氧基、2,2,-二氯乙氧基、2,2,2-三氯乙氧基、1-溴乙氧基、2-溴乙氧基、2,2-二溴乙氧基、2,2,2-三溴乙氧基、2-碘乙氧基、五氟乙氧基、3-氟丙氧基、3-氯丙氧基、3-溴丙氧基、1,3-二氟-2-丙氧基、3,3,3-三氟丙氧基、1,3-二氯-2-丙氧基、1,1,1-三氟-2-丙氧基、1-氯-3-氟-2-丙氧基、1,1,1,3,3,3-六氟-2-丙氧基、1,1,1,3,3,3-六氟-2-氯-2-丙氧基、2,2,3,3,3-五氟丙氧基、七氟异丙氧基、七氟-正丙氧基、4-氟丁氧基、4,4,4-三氟丁氧基、九氟-正丁氧基、九氟-2-丁氧基。
作为R5及R6表示的卤烷基硫基,可列举例如:单氟甲基硫基、二氟甲基硫基、三氟甲基硫基、单氯甲基硫基、二氯甲基硫基、三氯甲基硫基、单溴甲基硫基、二溴甲基硫基、三溴甲基硫基、1-氟乙基硫基、2-氟乙基硫基、2,2-二氟乙基硫基、2,2,2-三氟乙基硫基、2-氯-2,2-二氟乙基硫基、1-氯乙基硫基、2-氯乙基硫基、2,2,-二氯乙基硫基、2,2,2-三氯乙基硫基、1-溴乙基硫基、2-溴乙基硫基、2,2-二溴乙基硫基、2,2,2-三溴乙基硫基、2-碘乙基硫基、五氟乙基硫基、3-氟丙基硫基、3-氯丙基硫基、3-溴丙基硫基、1,3-二氟-2-丙基硫基、3,3,3-三氟丙基硫基、1,3-二氯-2-丙基硫基、1,1,1-三氟-2-丙基硫基、1-氯-3-氟-2-丙基硫基、1,1,1,3,3,3-六氟-2-丙基硫基、1,1,1,3,3,3-六氟-2-氯-2-丙基硫基、2,2,3,3,3-五氟丙基硫基、七氟异丙基硫基、七氟-正丙基硫基、4-氟丁基硫基、4,4,4-三氟丁基硫基、九氟-正丁基硫基、九氟-2-丁基硫基。
另外,R4表示氢原子、氰基或C1~C4的烷基,作为C1~C4的烷基,可列举:R1、R2、R3、R5及R6表示的烷基。
本发明的化合物为文献未记载的新型化合物,例如,可以由公知的起始化合物,按照下述反应式制造。
反应式
(式中,R1、R2、R3、R4、R5、R6、A及B如前述式[I]中所定义。)
可以通过使通式[II]表示的2-氨基烟酸衍生物和通式[III]表示的醇衍生物在缩合剂及碱存在下,在惰性溶剂中反应来制造通式[I]表示的本发明的2-氨基烟酸酯衍生物。
在此,化合物[II]及[III]为已经公知的化合物,或只要是本领域技术人员,就可以由公知化合物直接合成的化合物。
本反应中的反应温度通常为-20℃~120℃,优选为0℃~40℃的范围,就反应时间而言,在通常0.2小时~24小时,优选1小时~5小时的范围内进行。通式[III]表示的苯氧基己醇衍生物相对于通式[II]表示的2-氨基烟酸衍生物在通常1~5倍摩尔,优选1~1.5倍摩尔的范围内使用。
作为本反应中使用的缩合剂,可以例示例如:氰基磷酸二乙酯(DEPC)和羰基二咪唑(CDI)、1,3-二环己基碳二亚胺(DCC)、1-乙基-3-(3-二甲基氨基丙基)碳二亚胺盐酸盐、氯甲酸酯类、碘化2-氯-1-甲基吡啶鎓等,就其使用量而言,相对于通式[II]表示的2-氨基烟酸衍生物在通常1~3倍摩尔,优选1~1.5倍摩尔的范围内使用。
作为碱,可以列举例如:氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾等无机碱类;醋酸钠、醋酸钾等醋酸盐类;叔丁醇钾、甲醇钠、乙醇钠等金属醇盐类;三乙基胺、二异丙基乙基胺、1,8-二氮杂双环[5,4,0]十一碳-7-烯等叔胺类;吡啶、二甲基氨基吡啶等含氮芳香族化合物等。就碱的量而言,相对于通式[II]表示的2-氨基烟酸衍生物,在通常1~10倍摩尔,优选1~2倍摩尔的范围内使用。
本反应可以使用溶剂,也可以不使用,在使用溶剂的情况下,作为溶剂,只要不显著地阻碍本反应,就没有特别限制地使用各种溶剂,作为这样的溶剂,可以优选列举例如:二甲基醚、二乙基醚、二异丙基醚、二丁基醚、四氢呋喃、二噁烷等链状或环状醚类;苯、甲苯、二甲苯等芳香族烃类;二氯甲烷、氯仿、四氯化碳等卤代烃类;乙腈等腈类;醋酸甲酯、醋酸乙酯、醋酸丁酯等酯类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、1,3-二甲基-2-咪唑烷酮等极性溶剂,这些惰性溶剂可以单独使用,或2种以上混合使用。
反应后,目标化合物可以由含有其的反应系统,利用常规方法容易地分离,例如,可以用再结晶和柱色谱法等通过精制等来制备目标化合物。
本反应中所使用的通式[II]表示的2-氨基烟酸衍生物可以根据例如日本特开2010-083861号公报(专利文献1)中所记载的方法,由公知化合物直接合成。
本反应中所使用的通式[III]表示的醇衍生物可以根据例如Journal ofMedicinal Chemistry,43卷,1826页(2000)(非专利文献1)中所记载的方法,由公知化合物直接合成。
本发明的化合物可以为了防除诸如以下的果树类的病害而使用:鳄梨、杏、无花果、伊予柑、梅子、温州蜜柑、黄桃、牡蛎、臭橙、猕猴桃、李子、西洋梨、桶柑、凸顶柑(でこぽん)、梨、夏季蜜柑、油桃、八朔、番木瓜、枇杷、葡萄、朱栾、芒果、桃、柚子、苹果、柠檬等;谷类、例如大麦、小麦、水稻、玉米、薏苡、黑麦、陆稻等;薯类、例如甘薯、马铃薯、芋头、山芋等;蔬菜类、例如小豆、草莓、菜豆、豌豆、秋葵、芜菁、南瓜、甘蓝、黄瓜、牛蒡、豇豆、越瓜、西瓜、芹菜、蚕豆、萝卜、大豆、洋葱、甜菜、辣椒、冬瓜、番茄、茄子、苦瓜、胡萝卜、葱、白菜、西芹、青椒、丝瓜、甜瓜、莴苣等;特用作物、例如甘蔗、矮草、烟草、茶、油菜籽、爆裂型玉米(ポップ)等;花卉类、例如八仙花、香石竹、大丁草、勋章菊、菊花、金鱼草、金盏花、鼠尾草、满天星、香豌豆花、匙叶草属植物(Statice)、非洲堇、大丽花、梯牧草、飞燕草、洋桔梗、马鞭草、向日葵、荆棘类、秋海棠、矮牵牛、猩猩木、紫丁香、龙胆、迷迭香等;树木类、例如金合欢树类、枫树、橡树类、桂树、桐、榉、樱花类、臀鳍类、杜鹃类、山茶类、栎类、赤杨类、垂柳类。
作为成为对象的病害,可列举植物寄生性的丝状菌、细菌及放线菌类,具体而言,可列举:稻瘟病(Pyricularia oryzae)、胡麻叶斑病(Cochliobolusmiyabeanus)、纹枯病(Rizoctonia solani)、稻谷枯细菌病(Burcholderiaglumae)、白叶枯病(Xanthomonas oryzae pv.oryzae)、褐条病(Acidovoraxavenae subsp.avenae)、内颖褐变病(Erinia ananas)、叶梢褐变病(Pseudomonasfuscovaginae)、立枯细菌病(Burkholderia plantarii)等;麦类的白粉病(Erysiphe graminis)、赤霉病(Gibberella zeae)、赤锈病(Puccinia striiformis,P.graminis,P.recondita,P.hordei)、雪腐病(Typhula sp.,Micronectriellanivalis)、裸黑穗病(Ustilago tritici,U.nuda)、网腥黑穗病(Tilletia caries)、眼纹病(Pseudocercosporella herpotrichoides)、云形病(Rhynchosporium secalis)、叶枯病(Septoria tritici)、颖枯病(Leptosphaeria nodorum)、网斑病(Pyrenophora teres)、
豹纹病(Helminthosporium zonatum Ikata)、黑节病(Pseudomonassyringae pv.japonica)等;柑橘类的黑点病(Diaporthe citri)、柑桔疮痂病(Elsinoe fawcetti)、果实腐败病(Penicillium digitatum,P.italicum)、褐色腐败病(Phytophthora citrophthora,P.nicotianae)、黑星病(Phyllostictina citricarpa)、溃疡病(Xanthomonas campestris pv.citri)等;苹果的念珠菌病(Moniliniamali)、腐烂病(Valsa mali)、白粉病(Podosphaera leucotricha)、斑点落叶病(Alternaria mali)、黑星病(Venturia inaequalis)、黑点病(Mycospherella pomi)、炭疽病(Colletotrichum acutatum)、轮纹病(Botryosphaeria berengeriana)、赤星病(Gymnosporangium yamadae)、灰星病(Monilinia ffucticola)等;梨的黑星病(Venturia nashicola,V.pirina)、黑斑病(Alternaria kikuchiana)、蛙眼病(Gymnosporangium haraeanum)、灰星病(Monilinia fructigena)等;桃的灰星病(Monilinia fructicola)、黑星病(Cladosporium carpophilum)、
桑干枯病(Phomopsis sp.)、穿孔细菌病(Xanthomonas campestris pv.pruni)等;葡萄的黑痘病(Elinoe ampelina)、晚腐病(Colletotrichum acutatum)、白粉病(Uncinula necator)、锈病(Phakopsora ampelopsidis)、黑腐病(Guignardia bidwellii)、霜霉病(Plasmopara viticola)、灰星病(Moniliniafructigena)、黑星病(Cladosporium viticolum)、灰色霉病(Botrytis cinerea)、根癌瘤细菌病(Agrobacterium vitis)等;牡蛎的炭疽病(Gloeosporium kaki)、落叶病(Cercospora kaki,Mycoshaerella nawae)等;
大豆的紫斑病(Cercospora kikuchii)、黑痘病(Elsinoe glycines)、黑点病(Diaporthe phaseolorum var.sojae)、斑点细菌病(Pseudomonas savastanoi pv.glycinea)、细菌性斑疹病(Xanthomonas campestris pv.glycines)等;菜豆的炭疽病(Colletotrichum lindemthianum)、环孔枯萎病(Pseudomonas savastanoi pv.phaseolicola)、细菌性斑疹病(Xanthomonas campestris pv.phaseoli)等;落花生的黑斑病(Cercospora personata)、褐斑病(Cercospora arachidicola)等;豌豆的白粉病(Erysiphe pisi)等;瓜类的炭疽病(Colletotrichum lagenarium)、白粉病(Sphaerotheca fuliginea,Oidiopsis taurica)、蔓枯病(Didymella bryoniae)、蔓割病(Fusarium oxysporum)、霜霉病(Pseudoperonospora cubensis)、疫病(Phytophthora sp.)、苗立枯病(Pythium sp.)、斑点细菌病(Pseudomonassyringae pv.lachrymans)、褐斑细菌病(Xanthomonas campestris pv.cucuribitae)等;番茄的轮纹病(Alternaria solani)、叶霉病(Cladosporiumfulvum)、疫病(Phytophthora infestans)、青枯病(Ralstonia colanacearum)、
溃疡病(Clavibacter michiganense subsp.michiganense)、茎坏疽病(Pseudomonas corrugata)、软腐病(Erwinia carotovora subsp.carotovora)等;茄子的褐纹病(Phomopsis vexans)、白粉病(Erysiphe cichoracearum)、青枯病(Ralstonia colanacearum)等;油菜科蔬菜的黑斑病(Alternaria japonica)、白斑病(Cercosporella brassicae)、黑腐病(Xanthomonas campestris pv.campestris)、软腐病、腐败病(Pseudomonas syringae pv.marginalis)等;葱的锈病(Puccinia allii)等;马铃薯的夏疫病(Alternaria solani)、疫病(Phytophthora infestans)、叶腐病菌(Rhizoctonia solani)、软腐病、黑脚病(Erwinia carotovora subsp.atroseptica)、青枯病(Ralstonia colanacearum)、柑桔疮痂病(Streptomyces scabies,Streptomyces acidiscabies)等;草莓的白粉病(Sphaerotheca humuli)、青枯病(Ralstonia colanacearum)、芽枯细菌病(Pseudomonas marginalis pv.marginalis)、角斑细菌病(Xanthomonascampestris,Xanthomonas fragariae)等;茶的网饼病(Exobasidiumreticulatum)、白星病(Elsinoe leucospila)、野火病(Pseudomonas syringae pv.theae)、立枯病(Ralstonia solanacearum)、溃疡病(Xanthomonas campestris pv.theicola)等;
烟草的赤星病(Alternaria longipes)、白粉病、炭疽病(Colletotrichumtabacum)、霜霉病(Peronospora tabacina)、疫病(Phytophthora nicotianae)、空洞病(Erwinia carotovora subsp.carotovora)等;甜菜的褐斑病(Cercosporabeticola)、苗立枯病(Aphanomyces cochliodes)等;胡萝卜的黑叶枯病(Alternaria dauci)、瘤病(Rhizobacter dauci)、链霉菌柑桔疮痂病(Streptomycesscabies)、荆棘的黑星病(Diplocarpon rosae)、白粉病(Sphaerotheca pannosa)、根癌瘤病(Agrobacterium tumefaciens)等;菊花的褐斑病(Septoriachrysanthemi-indici)、白锈病(Puccinia horiana)、根癌瘤病等;各种作物的灰色霉病、菌核病(Sclerotinia sclerotiorum)等,但不一定限定于在此记载的菌类。
本发明的化合物可以以各种剂型使用。为了制成这些剂型,可以适当使用在农业和园艺用灭菌剂的技术领域中目前所使用的各种农药辅助剂。作为农业和园艺用灭菌剂的剂型,例如为乳剂、可湿性粉剂、颗粒可湿性粉剂、水溶剂、液剂、粉剂、胶悬剂、干胶悬剂、细粒剂、粒剂、片剂、油剂、喷雾剂、烟雾剂等。当然,也可以将本发明的化合物1种或组合2种以上而作为有效成分配合。
这种农药辅助剂可以以例如农业和园艺用灭菌剂的效果的提高、稳定化、分散性的提高等目的使用。作为农药辅助剂,可列举例如:载体(稀释剂)、展着剂、乳化剂、湿展剂、分散剂、崩解剂等。作为液体载体,可以列举:水和甲苯、二甲苯等芳香族烃、甲醇、丁醇、乙二醇等醇类、丙酮等酮类、二甲基甲酰胺等酰胺类、二甲基亚砜等亚砜类、甲基萘、环己烷、动植物油、脂肪酸等。另外,作为固体载体,可以使用粘土、高岭土、滑石、硅藻土、二氧化硅、碳酸钙、蒙脱石、膨润土、长石、石英、氧化铝、锯屑、硝基纤维素、淀粉、阿拉伯树胶等。
作为乳化剂和分散剂,可以使用通常的表面活性剂,可以使用例如:高级醇硫酸钠、硬脂基三甲基氯化铵、聚氧乙烯烷基苯基醚、月桂基甜菜碱等阴离子型表面活性剂、阳离子型表面活性剂、非离子型表面活性剂、两性离子型表面活性剂等。另外,可以使用:展着剂;二烷基磺基琥珀酸酯等湿展剂;羧甲基纤维素、聚乙烯醇等固着剂;木质素磺酸钠、月桂基硫酸钠等崩解剂等。
作为农业和园艺用灭菌剂中的有效成分的本发明的化合物的含量,从例如0.01~99.5质量%,优选0.5~90质量%的范围中选择,根据制剂形态、施用方法等各种条件适当确定即可,例如,可以以粉剂中含有约0.5~20质量%左右、优选1~10质量%的有效成分,可湿性粉剂中含有约1~90质量%左右、优选10~80质量%的有效成分,乳剂中含有约1~90质量%左右、优选10~40质量%的有效成分的方式制造。
例如,乳剂的情况下,相对于作为有效成分的本发明的化合物,可以混合溶剂及表面活性剂而制造原液的乳剂,进而,可以在使用该原液时用水稀释至规定浓度而施用。可湿性粉剂的情况下,将作为有效成分的本发明的化合物、固形载体及表面活性剂混合而制造原液,进而,可以在使用该原液时用水稀释至规定浓度而施用。粉剂的情况下,可以将作为有效成分的本发明的化合物、固形载体等混合而直接施用。在粒剂的情况下,可以通过将作为有效成分的本发明的化合物、固形载体及表面活性剂等混合并造粒来制造、直接施用。可是,上述的各制剂形态的制造方法并不限定于上述的方法,本领域技术人员可以根据有效成分的种类和施用目的等适当选择。
在农业和园艺用灭菌剂中,除作为有效成分的本发明的化合物以外,可以配合其它灭菌剂、杀虫剂、杀螨剂、除草剂、植物生长调整剂、肥料、土壤改良剂等任意的有效成分。由本发明的化合物构成的灭菌剂的施用方法没有特别限定,用茎叶散布、土壤处理、设施内的熏烟、熏茎等任一种方法均可以施用。例如,茎叶散布的情况下,可以将例如5~1000ppm、优选10~500ppm的浓度范围的溶液每10公亩以例如50~700升左右的施用量使用。土壤处理的情况下,可以将5~1000ppm的浓度范围的溶液每1m2以0.1~1升左右的施用量使用。
实施例
以下,对本发明进一步使用实施例、制剂例及试验例详细地进行说明,但本发明的范围并不受这些实施例、制剂例及试验例任何限定。
<实施例1>2-氨基烟酸-2-苯氧基苄基的合成
在2-氨基烟酸0.138g的二氯甲烷溶液中加入2-苯氧基己醇0.200g、1-乙基-3-(3-二甲基氨基丙基)碳二亚胺盐酸盐0.230g和4-二甲基氨基吡啶0.146g,加热回流3小时。冷却至室温后,用二氯甲烷萃取,将水层进一步用二氯甲烷萃取。将有机层合并并且用无水硫酸钠进行干燥。减压下浓缩,将得到的残渣用硅胶柱色谱法精制,由此得到表1中记载的本发明的化合物(编号1)、0.180g、油。此外,同样地操作,合成本发明的化合物。以下的表1中记载与实施例1同样地操作而制造的本发明的化合物。
表1
1)1H-NMR(CDCl3)δppm:4.41(2H,s)、6.55(1H,m)、6.93(3H,m)、7.08(1H,t)、7.18
(1H,t)、7.28-7.35(3H,m)、7.52(1H,d)、7.98(1H,d)、8.19(2H.d)。
2)1H-NMR(CDCl3)δppm:1.63(3H,d)、6.01-6.09(1H,q)、6.62(1H,m)、6.91(1H,d)、
7.03(1H,d)、7.09(1H,s)、7.11-7.18(1H,t)、7.29-7.38(4H,m)、8.19(1H,d)、8.22(1H,d)
3)1H-NMR(CDCl3)δppm:1.64(3H,d)、2.40(3H,s)、6.00-6.06(1H,q)、6.48(1H,d)、
6.92(1H,d)、7.02(1H,d)、7.08(1H,s)、7.09-7.15(1H,t)、7.30-7.38(4H,m)、8.06
(1H,d)
4)1H-NMR(CDCl3)δppm:1.65(3H,d)、6.07(1H,q)、6.62(1H,m)、7.01(4H,m)、7.12
(1H,t)、7.31-7.41(4H,m)、8.21(2H,m)。
5)1H-NMR(CDCl3)δppm:6.47(1H,s)、6.62(1H,m)、7.05-7.11(3H,m)、7.18(1H,t)、
7.22(1H,s)、7.30-7.45(4H,m)、8.12(1H,d)、8.29(1H,d)。
6)1H-NMR(CDCl3)δppm:2.41(3H,s)、5.31(2H,s)、6.48(1H,q)、7.05(4H,m)、
7.44(2H,d)、7.59(2H,d)、8.06(1H,d)
下面示出制剂例。需要说明的是,份表示质量份。
制剂例1乳剂
将本发明的化合物(10份)、二甲苯(60份)、N-甲基-2-吡咯烷酮(20份)及SORPOL 3005X(非离子型表面活性剂和阴离子型表面活性剂的混合物,东邦化学工业株式会社,商品名)(10份)均匀地混合溶解,得到乳剂。
制剂例2可湿性粉剂-1
将本发明的化合物(20份)、NIPSIL NS-K(白炭黑,东曹·二氧化硅株式会社,商品名)(20份)、高岭土粘土(高岭石,竹原化学工业株式会社,商品名)(70份)、サンエキスP-252(木质素磺酸钠,日本制纸化学株式会社,商品名)(5份)及Lennox P65L(烷基烯丙基磺酸盐,东邦化学工业株式会社,商品名)(5份)用空气磨均匀地混合粉碎,得到可湿性粉剂。
制剂例3可湿性粉剂-2
将本发明的化合物(20份)、NIPSIL NS-K(20份)、高岭土粘土(50份)、Lennox 1000C(萘磺酸盐缩合物,东邦化学工业株式会社,商品名)(5份)及SORPOL 5276(非离子型表面活性剂,东邦化学工业株式会社,商品名)(5份)用空气磨均匀地混合粉碎,得到可湿性粉剂。
制剂例4胶悬剂-1
将本发明的化合物(20份)分散于预先混合的丙二醇(5份)、SORPOL7933(阴离子型表面活性剂,东邦化学工业株式会社,商品名)(5份)、水(50份)中,制成浆液状混合物,接着,将该浆液状混合物用戴诺磨(ShinmaruEnterprises社)进行湿式粉碎后,添加预先在水(19.8份)中充分地混合分散有黄原胶(0.2份)的溶液,得到胶悬剂。
制剂例5胶悬剂-2
将本发明的化合物(20份)、ニユ一カルゲンFS-26(二辛基磺基琥珀酸酯和聚氧乙烯三苯乙烯基苯基醚的混合物,竹本油脂株式会社,商品名)(5份)、丙二醇(8份)、水(50份)预先混合,将该浆液状混合物用戴诺磨(Shinmaru Enterprises社)进行湿式粉碎。接着,将黄原胶(0.2份)与水(16.8份)充分地混合分散,制作凝胶状物,与粉碎的浆液充分地混合,得到胶悬剂。
接着,通过试验例显示:本发明的化合物作为灭菌剂的有效成分是有用的。需要说明的是,本发明的化合物用表1中记载的化合物编号表示,用于比较对照的化合物用下述的化合物标记(专利文献1的实施例中记载的化合物)表示。
试验例1:相对于黄瓜灰色霉病的试验
准备播种12天后的黄瓜(品种:相模半白)用于实验。残留该黄瓜的叶轴2cm左右,切取子叶部分。另做如下准备:在32cm×24cm×4.5cm(纵×横×高度)的塑料盒的底部铺设用水充分湿润的纸巾,在纸巾上放置支柱式的网。在该网上以叶子保持水平的方式排列上述的切取的子叶部分。在其子叶的中心部滴加黄瓜灰色霉病菌的胞子悬浮液(1×106个/ml)各50μl。其后,在子叶上覆盖直径6mm的纸盘。另将按照上述制剂例1制备的乳剂进一步用0.02%Tween20脱盐水水溶液稀释,制备规定浓度的稀释液。从纸盘上滴加该稀释液各50μl。在塑料盒上盖上盖子,置于20℃条件下72小时后,测定病斑直径,用下述式求出黄瓜灰色霉病的防除值。将结果示于表1。
防除值(%)=[1-(处理区病斑直径/无处理区病斑直径)]×100
表2
黄瓜灰色霉病
如上述表2所示,本发明的化合物与化合物A相比,灭菌活性高。
Claims (2)
1.一种2-氨基烟酸酯衍生物,其用下式[I]表示,
式中,R1表示氢原子或C1~C4的烷基,
R2表示氢原子、C1~C4的烷基,或R1和R2相互键合,表示
R3表示氢原子或C1~C4的烷基,
R4表示氢原子、氰基或C1~C4的烷基,
R5及R6相互独立地表示氢原子、卤原子、C1~C4的烷基、C1~C4的烷氧基、C1~C4的烷基硫基、C1~C4的烷基亚硫酰基、C1~C4的烷基磺酰基、硝基、氰基、C1~C4的卤烷基、C1~C4的卤烷氧基或C1~C4的卤烷基硫基,
A及B相互独立地表示次甲基(CH)或氮原子。
2.一种灭菌剂,其特征在于,含有权利要求1所述的2-氨基烟酸酯衍生物作为有效成分。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012150421 | 2012-07-04 | ||
JP2012-150421 | 2012-07-04 | ||
PCT/JP2013/060061 WO2014006945A1 (ja) | 2012-07-04 | 2013-04-02 | 2-アミノニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104520273A true CN104520273A (zh) | 2015-04-15 |
CN104520273B CN104520273B (zh) | 2016-08-24 |
Family
ID=49881710
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201380035233.9A Active CN104520273B (zh) | 2012-07-04 | 2013-04-02 | 2-氨基烟酸酯衍生物及以其为有效成分的灭菌剂 |
Country Status (20)
Country | Link |
---|---|
US (1) | US9096528B2 (zh) |
EP (1) | EP2871180B1 (zh) |
JP (1) | JP6114958B2 (zh) |
KR (1) | KR101629767B1 (zh) |
CN (1) | CN104520273B (zh) |
AU (1) | AU2013284775B2 (zh) |
BR (1) | BR112014032873B1 (zh) |
CA (1) | CA2877235C (zh) |
CL (1) | CL2014003643A1 (zh) |
CO (1) | CO7240428A2 (zh) |
ES (1) | ES2665561T3 (zh) |
HU (1) | HUE037765T2 (zh) |
IN (1) | IN2014DN10806A (zh) |
MA (1) | MA37825B1 (zh) |
PL (1) | PL2871180T3 (zh) |
PT (1) | PT2871180T (zh) |
RU (1) | RU2599725C2 (zh) |
UA (1) | UA111542C2 (zh) |
WO (1) | WO2014006945A1 (zh) |
ZA (1) | ZA201500742B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI631104B (zh) * | 2016-01-21 | 2018-08-01 | 阿格諾卡那休股份有限公司 | 2-胺基菸鹼酸苄酯衍生物之製造方法 |
CN110590653A (zh) * | 2018-06-12 | 2019-12-20 | 浙江省化工研究院有限公司 | 一种烟酸酯类化合物、其制备方法及应用 |
CN111567535A (zh) * | 2020-06-10 | 2020-08-25 | 青岛海利尔生物科技有限公司 | 一种含琥珀酸脱氢酶抑制剂的杀菌混合物及其应用 |
Families Citing this family (175)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6212773B2 (ja) * | 2013-08-01 | 2017-10-18 | アグロカネショウ株式会社 | 2−アミノニコチン酸ベンジル誘導体およびこれを有効成分とする殺菌剤 |
WO2015060378A1 (ja) * | 2013-10-25 | 2015-04-30 | 日本曹達株式会社 | アミノピリジン誘導体および農園芸用殺菌剤 |
JP6286693B2 (ja) * | 2013-12-25 | 2018-03-07 | アグロカネショウ株式会社 | 6−置換ニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 |
JP6174161B2 (ja) * | 2013-12-27 | 2017-08-02 | アグロカネショウ株式会社 | 2−アミノニコチン酸ベンジルエステル誘導体の製造方法 |
JP6331075B2 (ja) * | 2014-04-11 | 2018-05-30 | アグロカネショウ株式会社 | 3−アミノ−1h−ピラゾール−4−カルボン酸ベンジルエステル誘導体およびこれを有効成分とする殺菌剤 |
JPWO2015190601A1 (ja) * | 2014-06-13 | 2017-04-20 | アグロカネショウ株式会社 | 2−アシルアミノニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 |
US9902697B2 (en) | 2014-06-27 | 2018-02-27 | Agro-Kanesho Co., Ltd. | Method for producing 2-amino-6-methylnicotinic acid |
JP6331084B2 (ja) * | 2014-06-30 | 2018-05-30 | アグロカネショウ株式会社 | 2−ベンジルアミノニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 |
JP2017197433A (ja) * | 2014-09-12 | 2017-11-02 | 石原産業株式会社 | ニコチン酸エステル化合物、農園芸用殺菌剤及び植物病害の防除方法 |
EP3575286B1 (en) | 2017-01-26 | 2022-05-11 | Mitsui Chemicals Agro, Inc. | Pyridone compound and bactericide for agricultural and horticultural use, which uses said compound as active ingredient |
CA3059675A1 (en) | 2017-04-10 | 2018-10-18 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides comprising the same as active ingredients |
US11000038B2 (en) | 2017-04-10 | 2021-05-11 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
MX2019012174A (es) | 2017-04-11 | 2019-11-25 | Mitsui Chemicals Agro Inc | Compuestos de piridona y fungicidas agricolas y horticolas que contienen los mismos como ingredientes activos. |
EP3636636B1 (en) | 2017-06-08 | 2022-07-06 | Mitsui Chemicals Agro, Inc. | Pyridone compound and agricultural and horticultural fungicide |
WO2019007717A1 (en) * | 2017-07-06 | 2019-01-10 | Basf Se | PESTICIDE MIXTURES |
CA3104048A1 (en) | 2018-07-25 | 2020-01-30 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
GB201812692D0 (en) | 2018-08-03 | 2018-09-19 | Syngenta Participations Ag | Microbiocidal compounds |
TW202019901A (zh) | 2018-09-13 | 2020-06-01 | 瑞士商先正達合夥公司 | 殺有害生物活性唑-醯胺化合物 |
TW202023386A (zh) | 2018-09-13 | 2020-07-01 | 瑞士商先正達合夥公司 | 殺有害生物活性唑-醯胺化合物 |
AR116628A1 (es) | 2018-10-18 | 2021-05-26 | Syngenta Crop Protection Ag | Compuestos microbiocidas |
JP2022505376A (ja) | 2018-10-19 | 2022-01-14 | シンジェンタ パーティシペーションズ アーゲー | 殺有害生物活性アゾール-アミド化合物 |
EP3877380A1 (en) | 2018-11-05 | 2021-09-15 | Syngenta Participations Ag | Pesticidally active azole-amide compounds |
AR117183A1 (es) | 2018-11-30 | 2021-07-14 | Syngenta Crop Protection Ag | Derivados de tiazol microbiocidas |
AR117200A1 (es) | 2018-11-30 | 2021-07-21 | Syngenta Participations Ag | Derivados de tiazol microbiocidas |
WO2020165403A1 (en) | 2019-02-15 | 2020-08-20 | Syngenta Crop Protection Ag | Phenyl substituted thiazole derivatives as microbiocidal compounds |
WO2020169526A1 (en) | 2019-02-18 | 2020-08-27 | Syngenta Crop Protection Ag | Pesticidally-active cyanamide heterocyclic compounds |
EP3696175A1 (en) | 2019-02-18 | 2020-08-19 | Syngenta Crop Protection AG | Pesticidally active azole-amide compounds |
BR112021017646A2 (pt) | 2019-03-08 | 2021-11-16 | Syngenta Crop Protection Ag | Compostos de azol-amida ativos em termos pesticidas |
US20220306599A1 (en) | 2019-03-20 | 2022-09-29 | Syngenta Crop Protection Ag | Pesticidally active azole amide compounds |
BR112021018501A2 (pt) | 2019-03-20 | 2021-11-30 | Syngenta Crop Protection Ag | Compostos de azolamida ativos em termos pesticidas |
GB201903942D0 (en) | 2019-03-22 | 2019-05-08 | Syngenta Crop Protection Ag | Microbiocidal compounds |
US20220213063A1 (en) | 2019-03-22 | 2022-07-07 | Syngenta Crop Protection Ag | N-[l-(5-BROMO-2-PYRIMIDIN-2-YL-1,2,4-TRIAZOL-3-YL)ETHYL]-2-CYCLOPROPYL-6-(TRIFLUOROMETHYL)PYRIDINE-4-CARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS AS INSECTICIDES |
CN113646304B (zh) | 2019-03-27 | 2024-02-06 | 先正达农作物保护股份公司 | 杀微生物的噻唑衍生物 |
TW202102489A (zh) | 2019-03-29 | 2021-01-16 | 瑞士商先正達農作物保護公司 | 殺有害生物活性之二𠯤-醯胺化合物 |
MA55500A (fr) | 2019-04-05 | 2022-02-09 | Syngenta Crop Protection Ag | Composés de diazine-amide à action pesticide |
CA3132321A1 (en) | 2019-04-10 | 2020-10-15 | Clemens Lamberth | Fungicidal compositions |
WO2020208095A1 (en) | 2019-04-10 | 2020-10-15 | Syngenta Crop Protection Ag | Microbiocidal picolinamide derivatives |
JP2022528181A (ja) | 2019-04-11 | 2022-06-08 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物的に有効なジアジン-アミド化合物 |
AR119009A1 (es) | 2019-05-29 | 2021-11-17 | Syngenta Crop Protection Ag | Derivados de alcoxipiridina y alcoxipirimidina microbicidas |
JP2022534271A (ja) | 2019-05-29 | 2022-07-28 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺微生物誘導体 |
JP2022534914A (ja) | 2019-05-29 | 2022-08-04 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺微生物性誘導体 |
AR119011A1 (es) | 2019-05-29 | 2021-11-17 | Syngenta Crop Protection Ag | DERIVADOS DE [1,3]DIOXOLO[4,5-c]PIRIDIN-4-CARBOXAMIDA, COMPOSICIONES AGROQUÍMICAS QUE LOS COMPRENDEN Y SU EMPLEO COMO FUNGICIDA PARA CONTROLAR O PREVENIR LA INFESTACIÓN DE PLANTAS ÚTILES |
WO2020254530A1 (en) | 2019-06-18 | 2020-12-24 | Syngenta Crop Protection Ag | 7-sulfonyl-n-(1,3,4-thiadiazol-2-yl)-quinoxaline-6-carboxamide derivatives and the respective -benzimidazole-5-, -imidazo[4,5-b]pyridine-5-, -3h-furo[3,2b]pyridine-5-, -quinoline-2-, and -naphthalene-2-carboxamide derivatives as pesticides |
BR112021026861A2 (pt) | 2019-07-05 | 2022-02-22 | Syngenta Crop Protection Ag | Derivados de picolinamida microbiocidas |
GB201910037D0 (en) | 2019-07-12 | 2019-08-28 | Syngenta Crop Protection Ag | Microbiocidal compounds |
CN114340374B (zh) | 2019-08-21 | 2024-06-11 | 先正达参股股份有限公司 | 用于在种植期间处理种子的播种装置及方法 |
AU2020331684A1 (en) | 2019-08-21 | 2022-03-03 | Syngenta Participations Ag | Apparatus and method for converting existing sowing equipment |
US20220287221A1 (en) | 2019-08-21 | 2022-09-15 | Syngenta Participations Ag | Precision treatment and sowing or planting method and device |
EP4017243A1 (en) | 2019-08-21 | 2022-06-29 | Syngenta Participations Ag | High precision greenhouse seed and seedling treatment |
WO2021032634A1 (en) | 2019-08-21 | 2021-02-25 | Syngenta Participations Ag | Apparatus and method for reducing dust development in precision drill sowing |
JP2022545266A (ja) | 2019-08-23 | 2022-10-26 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物的に活性なピラジン-アミド化合物 |
GB201912595D0 (en) | 2019-09-02 | 2019-10-16 | Syngenta Crop Protection Ag | Plant growth regulator compounds |
UY38885A (es) | 2019-09-20 | 2021-04-30 | Syngenta Crop Protection Ag | Compuestos de azetidinil-, pirrolidinil-,piperdinil- o piperazinil-piridinil carbonilo pesticidamente activos |
CN114450280A (zh) | 2019-09-20 | 2022-05-06 | 先正达农作物保护股份公司 | 具有含硫和亚砜亚胺取代基的杀有害生物活性杂环衍生物 |
WO2021083936A1 (en) | 2019-11-01 | 2021-05-06 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic compounds |
WO2021110891A1 (en) | 2019-12-04 | 2021-06-10 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic amino compounds |
WO2021122645A1 (en) | 2019-12-20 | 2021-06-24 | Syngenta Crop Protection Ag | Pesticidally active azole-amide compounds |
BR112022012873A2 (pt) | 2019-12-31 | 2022-09-06 | Syngenta Crop Protection Ag | Derivados heterocíclicos ativos em termos pesticidas com substituintes contendo enxofre |
TW202132300A (zh) | 2020-01-06 | 2021-09-01 | 瑞士商先正達農作物保護公司 | 具有含硫取代基的殺有害生物活性雜環衍生物 |
WO2021144354A1 (en) | 2020-01-15 | 2021-07-22 | Syngenta Crop Protection Ag | Pesticidally-active bicyclic heteroaromatic compounds |
JP2023511201A (ja) | 2020-01-24 | 2023-03-16 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物的に活性な縮合二環式芳香族複素環式化合物 |
WO2021151926A1 (en) | 2020-01-30 | 2021-08-05 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic amino compounds |
JP2023513575A (ja) | 2020-02-11 | 2023-03-31 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物的に活性な環状アミン化合物 |
EP4110766A1 (en) | 2020-02-27 | 2023-01-04 | Syngenta Crop Protection AG | Pesticidally active diazine-bisamide compounds |
WO2021175822A1 (en) | 2020-03-02 | 2021-09-10 | Syngenta Crop Protection Ag | Pesticidally amidine-substituted benzoic acid amide compounds |
UY39115A (es) | 2020-03-05 | 2021-10-29 | Syngenta Crop Protection Ag | Mezclas fungicidas de derivados de arilo metoxiacrilato |
JP2023516197A (ja) | 2020-03-05 | 2023-04-18 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺菌性組成物 |
US20230111656A1 (en) | 2020-03-13 | 2023-04-13 | Syngenta Crop Protection Ag | Methods of controlling or preventing infestation of soybean plants by the phytopathogenic microorganism corynespora cassiicola |
US20230112306A1 (en) | 2020-03-13 | 2023-04-13 | Syngenta Crop Protection Ag | Methods of controlling or preventing infestation of soybean plants by the phytopathogenic microorganism corynespora cassiicola |
BR112022018269A2 (pt) | 2020-03-13 | 2022-12-27 | Syngenta Crop Protection Ag | Métodos de controle ou prevenção de infestação de plantas pelo microrganismo fitopatogênico corynespora cassiicola |
CN115334885A (zh) | 2020-03-13 | 2022-11-11 | 先正达农作物保护股份公司 | 控制或预防植物被植物病原性微生物多主棒孢菌、大豆灰斑病菌和/或大豆紫斑病菌侵染的方法 |
EP4117438A1 (en) | 2020-03-13 | 2023-01-18 | Syngenta Crop Protection AG | Methods of controlling or preventing infestation of plants by the phytopathogenic microorganism corynespora cassiicola |
EP4117435A1 (en) | 2020-03-13 | 2023-01-18 | Syngenta Crop Protection AG | Methods of controlling or preventing infestation of plants by the phytopathogenic microorganism corynespora cassiicola |
AR121733A1 (es) | 2020-04-08 | 2022-07-06 | Syngenta Crop Protection Ag | Derivados microbiocidas de tipo dihidro-(tiazina)oxazina de quinolina |
AR121734A1 (es) | 2020-04-08 | 2022-07-06 | Syngenta Crop Protection Ag | Derivados microbicidas de tipo dihidropirrolopirazina de quinolina |
BR112022020239A2 (pt) | 2020-04-08 | 2022-11-22 | Syngenta Crop Protection Ag | Derivados de quinolina di-hidro-(tiazina)oxazina microbiocidas |
WO2021213929A1 (en) | 2020-04-20 | 2021-10-28 | Syngenta Crop Protection Ag | Pesticidally active substituted 1,3-dihydro-2h-imidazo[4,5-c]pyridin-2-one derivatives with sulfur containing substituents |
CN115702149A (zh) | 2020-04-30 | 2023-02-14 | 先正达农作物保护股份公司 | 具有含硫取代基的杀有害生物活性的杂环衍生物 |
GB202006399D0 (en) | 2020-04-30 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal compounds |
GB202006386D0 (en) | 2020-04-30 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal Compounds |
GB202006480D0 (en) | 2020-05-01 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal compounds |
GB202006606D0 (en) | 2020-05-05 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal compounds |
WO2021224409A1 (en) | 2020-05-06 | 2021-11-11 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
IL298264A (en) | 2020-06-03 | 2023-01-01 | Syngenta Crop Protection Ag | microbiocidal derivatives |
JP2023527893A (ja) | 2020-06-03 | 2023-06-30 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺菌性組成物 |
EP4161277A1 (en) | 2020-06-03 | 2023-04-12 | Syngenta Crop Protection AG | Fungicidal compositions |
WO2022013417A1 (en) | 2020-07-17 | 2022-01-20 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2022017975A1 (en) | 2020-07-18 | 2022-01-27 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
CA3189161A1 (en) | 2020-08-31 | 2022-03-03 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
BR112023003835A2 (pt) | 2020-09-01 | 2023-04-04 | Syngenta Crop Protection Ag | Derivados heterocíclicos com substituintes contendo enxofre ativos em termos pesticidas |
EP4208447A1 (en) | 2020-09-02 | 2023-07-12 | Syngenta Crop Protection AG | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
US20230303565A1 (en) | 2020-09-02 | 2023-09-28 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
GB202013756D0 (en) | 2020-09-02 | 2020-10-14 | Syngenta Crop Protection Ag | Plant growth regulator compounds |
UY39411A (es) | 2020-09-09 | 2022-04-29 | Syngenta Crop Protection Ag | Derivados de indazolil pirazolo[3,4-c] piridina pesticídicamente activos con sustituyentes que contienen azufre |
GB202014840D0 (en) | 2020-09-21 | 2020-11-04 | Syngenta Crop Protection Ag | Microbiocidal compounds |
AR124276A1 (es) | 2020-10-22 | 2023-03-15 | Syngenta Crop Protection Ag | Compuestos reguladores del crecimiento vegetal |
WO2022101265A1 (en) | 2020-11-13 | 2022-05-19 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic compounds |
EP4281450A1 (en) | 2021-01-21 | 2023-11-29 | Syngenta Crop Protection AG | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2022157122A1 (en) | 2021-01-22 | 2022-07-28 | Syngenta Crop Protection Ag | Method for the control or suppression of phytopathogenic bacteria |
JP2024506253A (ja) | 2021-01-23 | 2024-02-13 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物的に有効な芳香族複素環式化合物 |
BR112023019532A2 (pt) | 2021-03-27 | 2023-10-31 | Syngenta Crop Protection Ag | Derivados de amida isonicotínicos microbicidas |
JP2024512694A (ja) | 2021-03-30 | 2024-03-19 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物的に活性な環状アミン化合物 |
UY39696A (es) | 2021-03-31 | 2022-10-31 | Syngenta Crop Protection Ag | Derivados microbiocidas de quinolin/quinoxalin-benzotiazina como agentes fungicidas, en particular c |
AR125342A1 (es) | 2021-04-16 | 2023-07-05 | Syngenta Crop Protection Ag | Compuestos de amina cíclica activos como plaguicidas |
AU2022260028A1 (en) | 2021-04-20 | 2023-10-12 | Syngenta Crop Protection Ag | Microbiocidal quinoline/quinoxaline isoquinoline derivatives |
CN117222314A (zh) | 2021-05-04 | 2023-12-12 | 先正达农作物保护股份公司 | 烯草酮用于昆虫控制的用途 |
IL308616A (en) | 2021-06-01 | 2024-01-01 | Syngenta Crop Protection Ag | TETRAHYDROISOQUINOLINE MICROBIOCIDAL DERIVATIVES |
CA3221102A1 (en) | 2021-06-02 | 2022-12-08 | Michel Muehlebach | Pesticidally active heterocyclic derivatives with sulfoximine containing substituents |
EP4352050A1 (en) | 2021-06-09 | 2024-04-17 | Syngenta Crop Protection AG | Pesticidally active diazine-amide compounds |
WO2022268648A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | 2-[3-[1 [(quinazolin-4-yl)amino]ethyl]pyrazin-2-yl]thiazole-5-carbonitrile derivatives and similar compounds as pesticides |
CN117597025A (zh) | 2021-07-02 | 2024-02-23 | 先正达农作物保护股份公司 | 精吡氟禾草灵用于昆虫控制的用途 |
EP4376616A1 (en) | 2021-07-27 | 2024-06-05 | Syngenta Crop Protection AG | Method for controlling diamide resistant pests & compounds therefor |
AU2022318251A1 (en) | 2021-07-29 | 2024-01-25 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic compounds |
CR20240051A (es) | 2021-08-02 | 2024-03-18 | Syngenta Crop Protection Ag | Derivados de pirazol microbiocidas |
EP4380363A1 (en) | 2021-08-05 | 2024-06-12 | Syngenta Crop Protection AG | Method for controlling diamide resistant pests & compounds therefor |
CN117836301A (zh) | 2021-08-10 | 2024-04-05 | 先正达农作物保护股份公司 | 作为杀有害生物剂的2,2-二氟-5h-[1,3]间二氧杂环戊烯并[4,5-f]异吲哚-7-酮衍生物 |
AR126729A1 (es) | 2021-08-10 | 2023-11-08 | Syngenta Crop Protection Ag | Mezcla fungicida |
EP4387449A1 (en) | 2021-08-19 | 2024-06-26 | Syngenta Crop Protection AG | Method for controlling diamide resistant pests & compounds therefor |
IL312020A (en) | 2021-10-14 | 2024-06-01 | Syngenta Crop Protection Ag | IMIDAZO[1,2-A]PYRIDINE DERIVATIVES |
WO2023072945A1 (en) | 2021-10-25 | 2023-05-04 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2023072849A1 (en) | 2021-10-27 | 2023-05-04 | Syngenta Crop Protection Ag | Pesticidally active pyridazinone compounds |
CA3235181A1 (en) | 2021-10-29 | 2023-05-04 | Lianhong Zhang | Fungicidal compositions comprising fludioxonil |
WO2023072785A1 (en) | 2021-10-29 | 2023-05-04 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2023089049A2 (en) | 2021-11-19 | 2023-05-25 | Syngenta Crop Protection Ag | Microbiocidal isonicotinic amide derivatives |
WO2023094304A1 (en) | 2021-11-25 | 2023-06-01 | Syngenta Crop Protection Ag | Microbiocidal heterobiaryl amide derivatives |
WO2023094303A1 (en) | 2021-11-25 | 2023-06-01 | Syngenta Crop Protection Ag | Microbiocidal heterobiaryl amide derivatives |
AR127799A1 (es) | 2021-12-02 | 2024-02-28 | Syngenta Crop Protection Ag | Composiciones fungicidas |
WO2023104714A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Pesticidally active pyridazinone compounds |
WO2023110710A1 (en) | 2021-12-13 | 2023-06-22 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests & compounds therefor |
EP4197333A1 (en) | 2021-12-15 | 2023-06-21 | Syngenta Crop Protection AG | Method for controlling diamide resistant pests & compounds therefor |
AR127922A1 (es) | 2021-12-15 | 2024-03-13 | Syngenta Crop Protection Ag | Derivados heterocíclicos bicíclicos microbiocidas |
WO2023110871A1 (en) | 2021-12-17 | 2023-06-22 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
AU2022413447A1 (en) | 2021-12-17 | 2024-06-13 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2023111215A1 (en) | 2021-12-17 | 2023-06-22 | Syngenta Crop Protection Ag | Microbiocidal pyridine-substituted benzothiazine derivatives |
WO2023118434A1 (en) | 2021-12-22 | 2023-06-29 | Globachem Nv | Pesticidally active amide compounds |
WO2023118011A1 (en) | 2021-12-22 | 2023-06-29 | Syngenta Crop Protection Ag | Microbiocidal aza-heterobiaryl derivatives |
CA3240915A1 (en) | 2021-12-22 | 2023-06-29 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2023139166A1 (en) | 2022-01-19 | 2023-07-27 | Syngenta Crop Protection Ag | Methods for controlling plant pathogens |
WO2023148206A1 (en) | 2022-02-02 | 2023-08-10 | Syngenta Crop Protection Ag | Microbiocidal n-amide derivatives |
WO2023148369A1 (en) | 2022-02-07 | 2023-08-10 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2023148368A1 (en) | 2022-02-07 | 2023-08-10 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2023166067A1 (en) | 2022-03-02 | 2023-09-07 | Syngenta Crop Protection Ag | Microbiocidal pyridazinone amide derivatives |
WO2023187191A1 (en) | 2022-04-01 | 2023-10-05 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2023209238A1 (en) | 2022-04-29 | 2023-11-02 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2023217989A1 (en) | 2022-05-12 | 2023-11-16 | Syngenta Crop Protection Ag | Alkoxy heteroaryl- carboxamide or thioamide compounds |
TW202408362A (zh) | 2022-06-21 | 2024-03-01 | 瑞士商先正達農作物保護公司 | 殺微生物的雙環雜環甲醯胺衍生物 |
WO2023247360A1 (en) | 2022-06-21 | 2023-12-28 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic compounds |
WO2024008567A1 (en) | 2022-07-07 | 2024-01-11 | Syngenta Crop Protection Ag | Precision application devices and compositions |
WO2024018016A1 (en) | 2022-07-21 | 2024-01-25 | Syngenta Crop Protection Ag | Crystalline forms of 1,2,4-oxadiazole fungicides |
WO2024017788A1 (en) | 2022-07-22 | 2024-01-25 | Syngenta Crop Protection Ag | Solid form of a heterocyclic amide derivative |
WO2024022910A1 (en) | 2022-07-26 | 2024-02-01 | Syngenta Crop Protection Ag | 1-[1-[2-(pyrimidin-4-yl)-1,2,4-triazol-3-yl]ethyl]-3-[2,4-dichloro-5-phenyl]urea derivatives and similar compounds as pesticides |
WO2024033374A1 (en) | 2022-08-11 | 2024-02-15 | Syngenta Crop Protection Ag | Novel arylcarboxamide or arylthioamide compounds |
WO2024038053A1 (en) | 2022-08-16 | 2024-02-22 | Syngenta Crop Protection Ag | New use of pydiflumetofen |
WO2024056732A1 (en) | 2022-09-16 | 2024-03-21 | Syngenta Crop Protection Ag | Pesticidally active cyclic amine compounds |
GB202214203D0 (en) | 2022-09-28 | 2022-11-09 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2024068655A1 (en) | 2022-09-28 | 2024-04-04 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2024068656A1 (en) | 2022-09-28 | 2024-04-04 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2024068947A1 (en) | 2022-09-30 | 2024-04-04 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2024068950A1 (en) | 2022-09-30 | 2024-04-04 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2024089023A1 (en) | 2022-10-25 | 2024-05-02 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2024089216A1 (en) | 2022-10-27 | 2024-05-02 | Syngenta Crop Protection Ag | Novel sulfur-containing heteroaryl carboxamide compounds |
WO2024089191A1 (en) | 2022-10-27 | 2024-05-02 | Syngenta Crop Protection Ag | Microbiocidal heterobicyclic dihydrooxadiazine derivatives |
WO2024094575A1 (en) | 2022-10-31 | 2024-05-10 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2024100069A1 (en) | 2022-11-08 | 2024-05-16 | Syngenta Crop Protection Ag | Microbiocidal pyridine derivatives |
WO2024100115A1 (en) | 2022-11-09 | 2024-05-16 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2024105104A1 (en) | 2022-11-16 | 2024-05-23 | Syngenta Crop Protection Ag | Microbiocidal tetrahydroisoquinoline derivatives |
WO2024110554A1 (en) | 2022-11-23 | 2024-05-30 | Syngenta Crop Protection Ag | N-[(1 -[2-[6-(pyridazin-3-yl]-1,2,4-triazol-3-yl]ethyl]-quinazolin-4-amine and n-[1-[3-(6-(pyridazin-3-yl)pyrazin-2-yl]ethyl]-8-quinazolin-4-amine derivatives as pesticides |
WO2024110215A1 (en) | 2022-11-24 | 2024-05-30 | Syngenta Crop Protection Ag | Pesticidally active cyclic amine compounds |
WO2024115509A1 (en) | 2022-11-29 | 2024-06-06 | Syngenta Crop Protection Ag | Microbiocidal tetrahydroisoquinoline derivatives |
WO2024115546A1 (en) | 2022-11-30 | 2024-06-06 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2024115512A1 (en) | 2022-11-30 | 2024-06-06 | Syngenta Crop Protection Ag | Microbiocidal tetrahydroisoquinoline derivatives |
WO2024126388A1 (en) | 2022-12-12 | 2024-06-20 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2024126404A1 (en) | 2022-12-14 | 2024-06-20 | Syngenta Crop Protection Ag | Imidazo[1,2-a]pyridine derivatives |
WO2024126650A1 (en) | 2022-12-15 | 2024-06-20 | Syngenta Crop Protection Ag | Novel bicyclic-carboxamide compounds useful as pesticides |
WO2024126407A1 (en) | 2022-12-16 | 2024-06-20 | Syngenta Crop Protection Ag | Benzimidazole derivatives |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09249648A (ja) * | 1996-03-18 | 1997-09-22 | Dainippon Ink & Chem Inc | 2,6−ジクロロイソニコチン酸フェノキシアルキルアミド誘導体及び農薬 |
JPH1072440A (ja) * | 1996-08-30 | 1998-03-17 | Dainippon Ink & Chem Inc | 2,6−ジクロロイソニコチン酸誘導体及び植物病害防除剤 |
WO2005068430A1 (ja) * | 2004-01-13 | 2005-07-28 | Kureha Corporation | 2,6−ジクロロイソニコチン酸ピリジルメチル誘導体、その製造方法および農園芸用病害防除剤 |
US20100168175A1 (en) * | 2008-12-18 | 2010-07-01 | Bayer Cropscience Ag | Atpenins |
CN101951771A (zh) * | 2008-02-27 | 2011-01-19 | 住友化学株式会社 | 用于控制或预防由植物病原体引起的植物病的农业用组合物 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8724252D0 (en) * | 1987-10-15 | 1987-11-18 | Ici Plc | Fungicides |
DE4319887A1 (de) | 1993-06-16 | 1994-12-22 | Hoechst Schering Agrevo Gmbh | Arylacetamide, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Fungizide |
EP0650961B1 (de) | 1993-11-02 | 1997-03-05 | Hoechst Aktiengesellschaft | Substituierte heterocyclische Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
KR100514941B1 (ko) | 1997-02-03 | 2005-09-15 | 다우 아그로사이언시즈 엘엘씨 | 살진균제로서 피리딘 환 상에 카복실산 유도체를 갖는 2-메톡시이미노-2-(피리디닐옥시메틸)페닐 아세트아미드 |
US5877177A (en) | 1997-06-17 | 1999-03-02 | Schering Corporation | Carboxy piperidylacetamide tricyclic compounds useful for inhibition of G-protein function and for treatment of proliferative diseases |
ATE296803T1 (de) | 1998-09-15 | 2005-06-15 | Syngenta Participations Ag | Als herbicide verwendbare pyridin-ketone |
JP2004149413A (ja) | 2000-06-30 | 2004-05-27 | Agro Kanesho Co Ltd | 有害生物の防除に有効なヒドラゾン誘導体又はその塩 |
JP2004051628A (ja) | 2002-05-28 | 2004-02-19 | Ishihara Sangyo Kaisha Ltd | ピリジン系化合物又はその塩、それらの製造方法及びそれらを含有する除草剤 |
US7307079B2 (en) | 2002-05-30 | 2007-12-11 | Solvay Pharmaceuticals, B.V. | 1,3,5-Triazine derivatives as ligands for human adenosine-A3 receptors |
CN1329388C (zh) | 2002-05-30 | 2007-08-01 | 索尔瓦药物有限公司 | 作为人腺苷-a3受体配体的新型1,3,5-三嗪衍生物 |
WO2004056735A1 (en) | 2002-12-23 | 2004-07-08 | Syngenta Participations Ag | 2,6-dihalo-4-(3,3-dichloro-allyloxy)-benzylalcohole derivatives having insecticidal and acaricidal properties |
US20080247964A1 (en) | 2006-05-08 | 2008-10-09 | Yuelian Xu | Substituted azaspiro derivatives |
US20100298314A1 (en) | 2006-12-20 | 2010-11-25 | Schering Corporation | Novel jnk inhibitors |
CN102216276A (zh) | 2008-09-11 | 2011-10-12 | 辉瑞大药厂 | 取代的杂芳基物 |
WO2011083304A1 (en) | 2010-01-05 | 2011-07-14 | Shire Llc | Prodrugs of opioids and uses thereof |
-
2013
- 2013-04-02 KR KR1020157002648A patent/KR101629767B1/ko active IP Right Grant
- 2013-04-02 PT PT138126651T patent/PT2871180T/pt unknown
- 2013-04-02 ES ES13812665.1T patent/ES2665561T3/es active Active
- 2013-04-02 AU AU2013284775A patent/AU2013284775B2/en active Active
- 2013-04-02 BR BR112014032873-0A patent/BR112014032873B1/pt active IP Right Grant
- 2013-04-02 US US14/412,130 patent/US9096528B2/en active Active
- 2013-04-02 CA CA2877235A patent/CA2877235C/en active Active
- 2013-04-02 EP EP13812665.1A patent/EP2871180B1/en active Active
- 2013-04-02 IN IN10806DEN2014 patent/IN2014DN10806A/en unknown
- 2013-04-02 CN CN201380035233.9A patent/CN104520273B/zh active Active
- 2013-04-02 WO PCT/JP2013/060061 patent/WO2014006945A1/ja active Application Filing
- 2013-04-02 HU HUE13812665A patent/HUE037765T2/hu unknown
- 2013-04-02 JP JP2014523622A patent/JP6114958B2/ja active Active
- 2013-04-02 PL PL13812665T patent/PL2871180T3/pl unknown
- 2013-04-02 RU RU2015103515/04A patent/RU2599725C2/ru active
- 2013-04-02 MA MA37825A patent/MA37825B1/fr unknown
- 2013-04-02 UA UAA201500284A patent/UA111542C2/uk unknown
-
2014
- 2014-12-31 CL CL2014003643A patent/CL2014003643A1/es unknown
-
2015
- 2015-01-23 CO CO15013754A patent/CO7240428A2/es unknown
- 2015-02-02 ZA ZA2015/00742A patent/ZA201500742B/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09249648A (ja) * | 1996-03-18 | 1997-09-22 | Dainippon Ink & Chem Inc | 2,6−ジクロロイソニコチン酸フェノキシアルキルアミド誘導体及び農薬 |
JPH1072440A (ja) * | 1996-08-30 | 1998-03-17 | Dainippon Ink & Chem Inc | 2,6−ジクロロイソニコチン酸誘導体及び植物病害防除剤 |
WO2005068430A1 (ja) * | 2004-01-13 | 2005-07-28 | Kureha Corporation | 2,6−ジクロロイソニコチン酸ピリジルメチル誘導体、その製造方法および農園芸用病害防除剤 |
CN101951771A (zh) * | 2008-02-27 | 2011-01-19 | 住友化学株式会社 | 用于控制或预防由植物病原体引起的植物病的农业用组合物 |
US20100168175A1 (en) * | 2008-12-18 | 2010-07-01 | Bayer Cropscience Ag | Atpenins |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI631104B (zh) * | 2016-01-21 | 2018-08-01 | 阿格諾卡那休股份有限公司 | 2-胺基菸鹼酸苄酯衍生物之製造方法 |
CN108473431A (zh) * | 2016-01-21 | 2018-08-31 | 阿格罗-金正株式会社 | 2-氨基烟酸苄酯衍生物的制造方法 |
CN108473431B (zh) * | 2016-01-21 | 2021-08-10 | 阿格罗-金正株式会社 | 2-氨基烟酸苄酯衍生物的制造方法 |
CN110590653A (zh) * | 2018-06-12 | 2019-12-20 | 浙江省化工研究院有限公司 | 一种烟酸酯类化合物、其制备方法及应用 |
CN110590653B (zh) * | 2018-06-12 | 2021-01-12 | 浙江省化工研究院有限公司 | 一种烟酸酯类化合物、其制备方法及应用 |
CN111567535A (zh) * | 2020-06-10 | 2020-08-25 | 青岛海利尔生物科技有限公司 | 一种含琥珀酸脱氢酶抑制剂的杀菌混合物及其应用 |
CN113966743A (zh) * | 2020-06-10 | 2022-01-25 | 青岛海利尔生物科技有限公司 | 一种含琥珀酸脱氢酶抑制剂的杀菌混合物及其应用 |
CN113966743B (zh) * | 2020-06-10 | 2023-07-28 | 青岛海利尔生物科技有限公司 | 一种含琥珀酸脱氢酶抑制剂的杀菌混合物及其应用 |
Also Published As
Publication number | Publication date |
---|---|
JPWO2014006945A1 (ja) | 2016-06-02 |
RU2599725C2 (ru) | 2016-10-10 |
AU2013284775B2 (en) | 2015-09-17 |
BR112014032873A2 (pt) | 2017-06-27 |
CA2877235A1 (en) | 2014-01-09 |
RU2015103515A (ru) | 2016-08-20 |
IN2014DN10806A (zh) | 2015-09-04 |
EP2871180B1 (en) | 2018-03-21 |
CL2014003643A1 (es) | 2015-07-31 |
US9096528B2 (en) | 2015-08-04 |
ES2665561T3 (es) | 2018-04-26 |
CN104520273B (zh) | 2016-08-24 |
CO7240428A2 (es) | 2015-04-17 |
AU2013284775A1 (en) | 2015-01-29 |
BR112014032873B1 (pt) | 2019-02-12 |
PL2871180T3 (pl) | 2018-08-31 |
PT2871180T (pt) | 2018-05-08 |
JP6114958B2 (ja) | 2017-04-19 |
MA20150409A1 (fr) | 2015-11-30 |
WO2014006945A1 (ja) | 2014-01-09 |
HUE037765T2 (hu) | 2018-09-28 |
CA2877235C (en) | 2016-09-20 |
US20150175551A1 (en) | 2015-06-25 |
UA111542C2 (uk) | 2016-05-10 |
EP2871180A4 (en) | 2016-02-24 |
KR101629767B1 (ko) | 2016-06-13 |
EP2871180A1 (en) | 2015-05-13 |
KR20150042781A (ko) | 2015-04-21 |
ZA201500742B (en) | 2016-09-28 |
MA37825B1 (fr) | 2016-06-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104520273A (zh) | 2-氨基烟酸酯衍生物及以其为有效成分的灭菌剂 | |
RU2573769C2 (ru) | Композиция для борьбы с заболеванием растений и способ борьбы с заболеванием растений | |
JP6286693B2 (ja) | 6−置換ニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 | |
BR112020002160A2 (pt) | derivado de azol, composto intermediário, método para produção de derivado de azol, agente químico agrícola ou hortícola e agente protetor para material industrial | |
JP2015089883A (ja) | 2−アミノニコチン酸ベンジルエステル誘導体およびこれを有効成分とする殺菌剤 | |
CN103068240A (zh) | 植物病害防除组合物及其用途 | |
JPWO2009028280A1 (ja) | ピラゾールカルボン酸誘導体及びその製造方法、並びに殺菌剤 | |
JP2009078991A (ja) | チオフェンカルボン酸誘導体およびその製造方法、並びに殺菌剤 | |
JP2009073818A (ja) | イソキサゾールカルボン酸誘導体及びその製造方法、並びに殺菌剤。 | |
JP6212773B2 (ja) | 2−アミノニコチン酸ベンジル誘導体およびこれを有効成分とする殺菌剤 | |
JP2010083763A (ja) | ピラゾール誘導体およびその製造方法、ならびに殺菌剤 | |
WO2011128989A1 (ja) | ピラジン-2-カルボキサミド誘導体及びこれを有効成分とする殺菌剤 | |
WO2016114164A1 (ja) | カルバメート化合物及びその用途 | |
WO2016114162A1 (ja) | カルバメート化合物及びその用途 | |
WO2016114161A1 (ja) | カルバメート化合物及びその用途 | |
JP6624077B2 (ja) | カルバメート化合物及びその用途 | |
JP6624075B2 (ja) | カルバメート化合物及びその用途 | |
WO2017090664A1 (ja) | キノキサリルイソキノリン化合物 | |
JP2012201640A (ja) | ベンゼン−2−カルボキサミド誘導体およびこれを有効成分とする殺菌剤 | |
JP6331084B2 (ja) | 2−ベンジルアミノニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 | |
JP6331075B2 (ja) | 3−アミノ−1h−ピラゾール−4−カルボン酸ベンジルエステル誘導体およびこれを有効成分とする殺菌剤 | |
JP2020045292A (ja) | ピぺリジン誘導体又はその塩及びこれを有効成分として含有する農園芸用殺菌剤 | |
WO2015190601A1 (ja) | 2-アシルアミノニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 | |
JPH07187918A (ja) | 殺菌剤組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CP03 | Change of name, title or address |
Address after: 1-8-3 Marunouchi, Chiyoda ku, Tokyo, Japan Patentee after: AGRO-KANESHO CO.,LTD. Country or region after: Japan Address before: Tokyo, Japan Patentee before: AGRO-KANESHO CO.,LTD. Country or region before: Japan |