WO2023176458A1 - Disinfecting composition containing thiazole carboxylic acid hydrazide compound - Google Patents
Disinfecting composition containing thiazole carboxylic acid hydrazide compound Download PDFInfo
- Publication number
- WO2023176458A1 WO2023176458A1 PCT/JP2023/007646 JP2023007646W WO2023176458A1 WO 2023176458 A1 WO2023176458 A1 WO 2023176458A1 JP 2023007646 W JP2023007646 W JP 2023007646W WO 2023176458 A1 WO2023176458 A1 WO 2023176458A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- formula
- propyl
- compounds
- reaction
- Prior art date
Links
- -1 thiazole carboxylic acid hydrazide compound Chemical class 0.000 title claims abstract description 601
- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 230000000249 desinfective effect Effects 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract description 98
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 96
- 201000010099 disease Diseases 0.000 claims abstract description 94
- 239000004480 active ingredient Substances 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims description 343
- 238000000034 method Methods 0.000 claims description 61
- IJVLVRYLIMQVDD-UHFFFAOYSA-N 1,3-thiazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CS1 IJVLVRYLIMQVDD-UHFFFAOYSA-N 0.000 claims description 49
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 239000002689 soil Substances 0.000 claims description 21
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 13
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 10
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 244000000003 plant pathogen Species 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 7
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 230000001954 sterilising effect Effects 0.000 claims description 3
- 230000001276 controlling effect Effects 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 152
- 241000894006 Bacteria Species 0.000 description 56
- 241000196324 Embryophyta Species 0.000 description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 53
- 241000233866 Fungi Species 0.000 description 50
- 241000233679 Peronosporaceae Species 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 241000223218 Fusarium Species 0.000 description 25
- 239000000126 substance Substances 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 238000012360 testing method Methods 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 19
- 240000003768 Solanum lycopersicum Species 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- 238000009472 formulation Methods 0.000 description 16
- 241000221785 Erysiphales Species 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 206010027146 Melanoderma Diseases 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 13
- 241000234282 Allium Species 0.000 description 13
- 241000223600 Alternaria Species 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 241001465180 Botrytis Species 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000417 fungicide Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 240000008067 Cucumis sativus Species 0.000 description 11
- 241000233614 Phytophthora Species 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 241001223281 Peronospora Species 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 230000000855 fungicidal effect Effects 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 9
- 241000222199 Colletotrichum Species 0.000 description 9
- 241000918585 Pythium aphanidermatum Species 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 240000007124 Brassica oleracea Species 0.000 description 8
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 8
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 8
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 241000233639 Pythium Species 0.000 description 8
- 241000221662 Sclerotinia Species 0.000 description 8
- 241000209140 Triticum Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000011081 inoculation Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 7
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 7
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 7
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
- 239000010452 phosphate Substances 0.000 description 7
- 150000003222 pyridines Chemical class 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 241000233622 Phytophthora infestans Species 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 206010039509 Scab Diseases 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 241000589634 Xanthomonas Species 0.000 description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 229940088710 antibiotic agent Drugs 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- 230000003902 lesion Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 5
- 241001163841 Albugo ipomoeae-panduratae Species 0.000 description 5
- 241000193830 Bacillus <bacterium> Species 0.000 description 5
- 240000002791 Brassica napus Species 0.000 description 5
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 5
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 241000221787 Erysiphe Species 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 241001558929 Sclerotium <basidiomycota> Species 0.000 description 5
- 241001533598 Septoria Species 0.000 description 5
- 241000221566 Ustilago Species 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 244000000005 bacterial plant pathogen Species 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000003449 preventive effect Effects 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 241000919511 Albugo Species 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- 235000011293 Brassica napus Nutrition 0.000 description 4
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 235000002568 Capsicum frutescens Nutrition 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 241000207199 Citrus Species 0.000 description 4
- 241000228437 Cochliobolus Species 0.000 description 4
- 235000009849 Cucumis sativus Nutrition 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 240000009088 Fragaria x ananassa Species 0.000 description 4
- 241001620302 Glomerella <beetle> Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 244000070406 Malus silvestris Species 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 241000233616 Phytophthora capsici Species 0.000 description 4
- 241001281802 Pseudoperonospora Species 0.000 description 4
- 241000221300 Puccinia Species 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 244000088415 Raphanus sativus Species 0.000 description 4
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 4
- 241001361634 Rhizoctonia Species 0.000 description 4
- 235000004789 Rosa xanthina Nutrition 0.000 description 4
- 241001247145 Sebastes goodei Species 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 235000002597 Solanum melongena Nutrition 0.000 description 4
- 244000061458 Solanum melongena Species 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 4
- 244000061456 Solanum tuberosum Species 0.000 description 4
- 235000009337 Spinacia oleracea Nutrition 0.000 description 4
- 244000300264 Spinacia oleracea Species 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 241000219094 Vitaceae Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000003443 antiviral agent Substances 0.000 description 4
- 239000005667 attractant Substances 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 235000020971 citrus fruits Nutrition 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 244000000004 fungal plant pathogen Species 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052987 metal hydride Inorganic materials 0.000 description 4
- 150000004681 metal hydrides Chemical class 0.000 description 4
- 229910000000 metal hydroxide Inorganic materials 0.000 description 4
- 150000004692 metal hydroxides Chemical class 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 238000003359 percent control normalization Methods 0.000 description 4
- 239000005648 plant growth regulator Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 4
- 229910000105 potassium hydride Inorganic materials 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000003586 protic polar solvent Substances 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- 241000234270 Amaryllidaceae Species 0.000 description 3
- 241001444083 Aphanomyces Species 0.000 description 3
- 235000017647 Brassica oleracea var italica Nutrition 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 241000609458 Corynespora Species 0.000 description 3
- 241000219130 Cucurbita pepo subsp. pepo Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 241001085796 Hyaloperonospora Species 0.000 description 3
- 241000207923 Lamiaceae Species 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 241001518729 Monilinia Species 0.000 description 3
- 241000233654 Oomycetes Species 0.000 description 3
- 235000006089 Phaseolus angularis Nutrition 0.000 description 3
- 241001503464 Plasmodiophora Species 0.000 description 3
- 241000899394 Pseudocercospora Species 0.000 description 3
- 241000589516 Pseudomonas Species 0.000 description 3
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 3
- 241000231139 Pyricularia Species 0.000 description 3
- 240000000111 Saccharum officinarum Species 0.000 description 3
- 235000007201 Saccharum officinarum Nutrition 0.000 description 3
- 235000003434 Sesamum indicum Nutrition 0.000 description 3
- 244000040738 Sesamum orientale Species 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 3
- 235000010711 Vigna angularis Nutrition 0.000 description 3
- 240000007098 Vigna angularis Species 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000003973 irrigation Methods 0.000 description 3
- 230000002262 irrigation Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000005645 nematicide Substances 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- QHXLIQMGIGEHJP-UHFFFAOYSA-N picoline - borane complex Substances [B].CC1=CC=CC=N1 QHXLIQMGIGEHJP-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000004071 soot Substances 0.000 description 3
- 230000007480 spreading Effects 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 235000021012 strawberries Nutrition 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- YJINQJFQLQIYHX-UHFFFAOYSA-N trans-11-tetradecenyl acetate Natural products CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 description 3
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 2
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 2
- IQVNEKKDSLOHHK-FNCQTZNRSA-N (E,E)-hydramethylnon Chemical compound N1CC(C)(C)CNC1=NN=C(/C=C/C=1C=CC(=CC=1)C(F)(F)F)\C=C\C1=CC=C(C(F)(F)F)C=C1 IQVNEKKDSLOHHK-FNCQTZNRSA-N 0.000 description 2
- ZFHGXWPMULPQSE-UKSCLKOJSA-N (Z)-(1R)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@H]1C(C)(C)[C@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-UKSCLKOJSA-N 0.000 description 2
- 239000005683 (Z)-11-Hexadecenal Substances 0.000 description 2
- AMTITFMUKRZZEE-WAYWQWQTSA-N (Z)-hexadec-11-enal Chemical compound CCCC\C=C/CCCCCCCCCC=O AMTITFMUKRZZEE-WAYWQWQTSA-N 0.000 description 2
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 description 2
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 2
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical class NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 2
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- YEKPNMQQSPHKBP-UHFFFAOYSA-N 2-methyl-6-nitrobenzoic anhydride Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C(=O)OC(=O)C1=C(C)C=CC=C1[N+]([O-])=O YEKPNMQQSPHKBP-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 2
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 2
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 2
- MFFQOUCMBNXSBK-PLNGDYQASA-N 9Z-Dodecenyl acetate Chemical compound CC\C=C/CCCCCCCCOC(C)=O MFFQOUCMBNXSBK-PLNGDYQASA-N 0.000 description 2
- 239000005652 Acrinathrin Substances 0.000 description 2
- 241000223602 Alternaria alternata Species 0.000 description 2
- 241000208173 Apiaceae Species 0.000 description 2
- 235000003276 Apios tuberosa Nutrition 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000010744 Arachis villosulicarpa Nutrition 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000235349 Ascomycota Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000000832 Ayote Nutrition 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- 241000221198 Basidiomycota Species 0.000 description 2
- 241001429251 Beet necrotic yellow vein virus Species 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 241000123649 Botryotinia Species 0.000 description 2
- 241000233684 Bremia Species 0.000 description 2
- 241000233685 Bremia lactucae Species 0.000 description 2
- 240000001548 Camellia japonica Species 0.000 description 2
- 241000221866 Ceratocystis Species 0.000 description 2
- 241001157813 Cercospora Species 0.000 description 2
- 241000871189 Chenopodiaceae Species 0.000 description 2
- 239000005944 Chlorpyrifos Substances 0.000 description 2
- 244000241235 Citrullus lanatus Species 0.000 description 2
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 2
- 241000222290 Cladosporium Species 0.000 description 2
- 241000723377 Coffea Species 0.000 description 2
- 241000207782 Convolvulaceae Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 2
- 241000219112 Cucumis Species 0.000 description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
- 235000009854 Cucurbita moschata Nutrition 0.000 description 2
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 2
- 235000003954 Cucurbita pepo var melopepo Nutrition 0.000 description 2
- 241000219104 Cucurbitaceae Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 240000006497 Dianthus caryophyllus Species 0.000 description 2
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 2
- 239000005762 Dimoxystrobin Substances 0.000 description 2
- 241000510928 Erysiphe necator Species 0.000 description 2
- KCOCSOWTADCKOL-UHFFFAOYSA-N Ethidimuron Chemical compound CCS(=O)(=O)C1=NN=C(N(C)C(=O)NC)S1 KCOCSOWTADCKOL-UHFFFAOYSA-N 0.000 description 2
- 239000005902 Flupyradifurone Substances 0.000 description 2
- 239000005560 Foramsulfuron Substances 0.000 description 2
- 241001600161 Fulvia Species 0.000 description 2
- 241000461774 Gloeosporium Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000208818 Helianthus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000005567 Imazosulfuron Substances 0.000 description 2
- NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 description 2
- 239000005796 Ipconazole Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001533590 Junonia Species 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 241000234280 Liliaceae Species 0.000 description 2
- 240000001585 Limonium sinuatum Species 0.000 description 2
- 239000005949 Malathion Substances 0.000 description 2
- 239000005584 Metsulfuron-methyl Substances 0.000 description 2
- 241000131448 Mycosphaerella Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 235000010676 Ocimum basilicum Nutrition 0.000 description 2
- 240000007926 Ocimum gratissimum Species 0.000 description 2
- JAYZFNIOOYPIAH-UHFFFAOYSA-N Oxydeprofos Chemical compound CCS(=O)CC(C)SP(=O)(OC)OC JAYZFNIOOYPIAH-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241001561016 Physoderma Species 0.000 description 2
- 235000010582 Pisum sativum Nutrition 0.000 description 2
- 240000004713 Pisum sativum Species 0.000 description 2
- 241000233626 Plasmopara Species 0.000 description 2
- 241000896242 Podosphaera Species 0.000 description 2
- 241000219050 Polygonaceae Species 0.000 description 2
- 241000132144 Polymyxa betae Species 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- 241000220324 Pyrus Species 0.000 description 2
- 241000109329 Rosa xanthina Species 0.000 description 2
- 241000220222 Rosaceae Species 0.000 description 2
- 241001093501 Rutaceae Species 0.000 description 2
- 241000576755 Sclerotia Species 0.000 description 2
- 241001300361 Sclerotinia borealis Species 0.000 description 2
- 241001535067 Setosphaeria Species 0.000 description 2
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 2
- 241001219482 Spongospora Species 0.000 description 2
- 241000187747 Streptomyces Species 0.000 description 2
- 229930182692 Strobilurin Natural products 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 2
- 235000004031 Viola x wittrockiana Nutrition 0.000 description 2
- 244000195452 Wasabia japonica Species 0.000 description 2
- 235000000760 Wasabia japonica Nutrition 0.000 description 2
- AMTITFMUKRZZEE-UHFFFAOYSA-N Z11-16:Ald Natural products CCCCC=CCCCCCCCCCC=O AMTITFMUKRZZEE-UHFFFAOYSA-N 0.000 description 2
- 235000006886 Zingiber officinale Nutrition 0.000 description 2
- 244000273928 Zingiber officinale Species 0.000 description 2
- 241000234299 Zingiberaceae Species 0.000 description 2
- LALGZGDVRILFNW-UHFFFAOYSA-N [2,5-dimethyl-4-[2-methylsulfonyl-4-(trifluoromethyl)benzoyl]pyrazol-3-yl] 1,3-dimethylpyrazole-4-carboxylate Chemical compound CN1N=C(C(=C1)C(=O)OC1=C(C(=NN1C)C)C(C1=C(C=C(C=C1)C(F)(F)F)S(=O)(=O)C)=O)C LALGZGDVRILFNW-UHFFFAOYSA-N 0.000 description 2
- FMPFURNXXAKYNE-UHFFFAOYSA-N [2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]quinolin-4-yl] methyl carbonate Chemical compound C1=C2C(OC(=O)OC)=C(C)C(CC)=NC2=CC(C)=C1OC1=CC=C(OC(F)(F)F)C=C1 FMPFURNXXAKYNE-UHFFFAOYSA-N 0.000 description 2
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- YLFSVIMMRPNPFK-WEQBUNFVSA-N acrinathrin Chemical compound CC1(C)[C@@H](\C=C/C(=O)OC(C(F)(F)F)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YLFSVIMMRPNPFK-WEQBUNFVSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- LRZWFURXIMFONG-HRSIRGMGSA-N afidopyropen Chemical compound C([C@@]1(C)[C@H]2[C@]([C@H]3[C@@H](O)C=4C(=O)OC(=CC=4O[C@]3(C)[C@@H](O)C2)C=2C=NC=CC=2)(C)CC[C@@H]1OC(=O)C1CC1)OC(=O)C1CC1 LRZWFURXIMFONG-HRSIRGMGSA-N 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 150000003927 aminopyridines Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
- 150000003936 benzamides Chemical class 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- ZYXYTGQFPZEUFX-UHFFFAOYSA-N benzpyrimoxan Chemical compound O1C(OCCC1)C=1C(=NC=NC=1)OCC1=CC=C(C=C1)C(F)(F)F ZYXYTGQFPZEUFX-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 2
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 235000018597 common camellia Nutrition 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- LSFUGNKKPMBOMG-UHFFFAOYSA-N cycloprothrin Chemical compound ClC1(Cl)CC1(C=1C=CC=CC=1)C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 LSFUGNKKPMBOMG-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- WEBQKRLKWNIYKK-UHFFFAOYSA-N demeton-S-methyl Chemical compound CCSCCSP(=O)(OC)OC WEBQKRLKWNIYKK-UHFFFAOYSA-N 0.000 description 2
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 2
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- NHFDKKSSQWCEES-UHFFFAOYSA-N dihydrogen phosphate;tris(2-hydroxyethyl)azanium Chemical compound OP(O)(O)=O.OCCN(CCO)CCO NHFDKKSSQWCEES-UHFFFAOYSA-N 0.000 description 2
- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000000967 entomopathogenic effect Effects 0.000 description 2
- BVQZKSIIHOVGPR-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.OC.CCOC(C)=O BVQZKSIIHOVGPR-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- PHCCDUCBMCYSNQ-UHFFFAOYSA-N fluazaindolizine Chemical compound COC1=CC=C(Cl)C(S(=O)(=O)NC(=O)C=2N=C3C(Cl)=CC(=CN3C=2)C(F)(F)F)=C1 PHCCDUCBMCYSNQ-UHFFFAOYSA-N 0.000 description 2
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- QOIYTRGFOFZNKF-UHFFFAOYSA-N flupyradifurone Chemical compound C=1C(=O)OCC=1N(CC(F)F)CC1=CC=C(Cl)N=C1 QOIYTRGFOFZNKF-UHFFFAOYSA-N 0.000 description 2
- PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 description 2
- 235000008397 ginger Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 235000021021 grapes Nutrition 0.000 description 2
- 238000003898 horticulture Methods 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 208000006278 hypochromic anemia Diseases 0.000 description 2
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 150000002547 isoxazolines Chemical class 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 229960000453 malathion Drugs 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 description 2
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- OXWFFWJKUNMMSO-UHFFFAOYSA-N n-octyl-n'-[2-(octylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCNCCNCCNCCCCCCCC OXWFFWJKUNMMSO-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
- 150000004045 organic chlorine compounds Chemical class 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 235000021017 pears Nutrition 0.000 description 2
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 2
- 229960000490 permethrin Drugs 0.000 description 2
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 2
- 150000008048 phenylpyrazoles Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000003375 plant hormone Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 2
- 235000015136 pumpkin Nutrition 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 239000002728 pyrethroid Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 2
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 description 2
- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- KAATUXNTWXVJKI-GGPKGHCWSA-N (1R)-trans-(alphaS)-cypermethrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-GGPKGHCWSA-N 0.000 description 1
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
- VIXCLRUCUMWJFF-KGLIPLIRSA-N (1R,5S)-benzobicyclon Chemical compound CS(=O)(=O)c1ccc(C(=O)C2=C(Sc3ccccc3)[C@H]3CC[C@H](C3)C2=O)c(Cl)c1 VIXCLRUCUMWJFF-KGLIPLIRSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 description 1
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
- AGMMRUPNXPWLGF-AATRIKPKSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methyl 2,2-dimethyl-3-[(e)-prop-1-enyl]cyclopropane-1-carboxylate Chemical class CC1(C)C(/C=C/C)C1C(=O)OCC1=C(F)C(F)=C(C)C(F)=C1F AGMMRUPNXPWLGF-AATRIKPKSA-N 0.000 description 1
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 description 1
- IXVMHGVQKLDRKH-YEJCTVDLSA-N (22s,23s)-epibrassinolide Chemical compound C1OC(=O)[C@H]2C[C@H](O)[C@H](O)C[C@]2(C)[C@H]2CC[C@]3(C)[C@@H]([C@H](C)[C@H](O)[C@@H](O)[C@H](C)C(C)C)CC[C@H]3[C@@H]21 IXVMHGVQKLDRKH-YEJCTVDLSA-N 0.000 description 1
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- LZTIMERBDGGAJD-SNAWJCMRSA-N (2e)-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)\C=C1/NCCCS1 LZTIMERBDGGAJD-SNAWJCMRSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XHSDUVBUZOUAOQ-WJQMYRPNSA-N (3e,3ar,8bs)-3-[[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxymethylidene]-4,8b-dihydro-3ah-indeno[1,2-b]furan-2-one Chemical compound O1C(=O)C(C)=C[C@@H]1O\C=C/1C(=O)O[C@@H]2C3=CC=CC=C3C[C@@H]2\1 XHSDUVBUZOUAOQ-WJQMYRPNSA-N 0.000 description 1
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- PWWPULQZEAPTTB-UHFFFAOYSA-N (4-phenoxyphenyl)methyl 2-amino-6-methylpyridine-3-carboxylate Chemical compound NC1=NC(C)=CC=C1C(=O)OCC(C=C1)=CC=C1OC1=CC=CC=C1 PWWPULQZEAPTTB-UHFFFAOYSA-N 0.000 description 1
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 1
- BKBSMMUEEAWFRX-NBVRZTHBSA-N (E)-flumorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(F)=CC=1)=C\C(=O)N1CCOCC1 BKBSMMUEEAWFRX-NBVRZTHBSA-N 0.000 description 1
- GSAAJQNJNPBBSX-UHFFFAOYSA-N (E)-form-9-Tetradecen-1-ol Natural products CCCCC=CCCCCCCCCO GSAAJQNJNPBBSX-UHFFFAOYSA-N 0.000 description 1
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 1
- FFQPZWRNXKPNPX-INIZCTEOSA-N (S)-beflubutamid Chemical compound O([C@@H](CC)C(=O)NCC=1C=CC=CC=1)C1=CC=C(F)C(C(F)(F)F)=C1 FFQPZWRNXKPNPX-INIZCTEOSA-N 0.000 description 1
- ADDQHLREJDZPMT-AWEZNQCLSA-N (S)-metamifop Chemical compound O=C([C@@H](OC=1C=CC(OC=2OC3=CC(Cl)=CC=C3N=2)=CC=1)C)N(C)C1=CC=CC=C1F ADDQHLREJDZPMT-AWEZNQCLSA-N 0.000 description 1
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 description 1
- OVXMBIVWNJDDSM-UHFFFAOYSA-N (benzhydrylideneamino) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)ON=C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OVXMBIVWNJDDSM-UHFFFAOYSA-N 0.000 description 1
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 description 1
- IKNXXTIMVROREQ-WXXKFALUSA-N (e)-but-2-enedioic acid;[2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl]-imidazol-1-ylmethanone Chemical compound OC(=O)\C=C\C(O)=O.C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1.C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 IKNXXTIMVROREQ-WXXKFALUSA-N 0.000 description 1
- USGUVNUTPWXWBA-JRIXXDKMSA-N (e,2s)-2-amino-4-(2-aminoethoxy)but-3-enoic acid Chemical compound NCCO\C=C\[C@H](N)C(O)=O USGUVNUTPWXWBA-JRIXXDKMSA-N 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
- OXDSKEQSEGDAFN-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenylmethanesulfonamide Chemical class FC(F)(F)S(=O)(=O)NC1=CC=CC=C1 OXDSKEQSEGDAFN-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical class NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 description 1
- WNWOTMKHOLCHRJ-UHFFFAOYSA-N 1,4-dihydrotriazol-5-one Chemical class O=C1CN=NN1 WNWOTMKHOLCHRJ-UHFFFAOYSA-N 0.000 description 1
- MVHWKYHDYCGNQN-UHFFFAOYSA-N 1,5-dichloro-3-fluoro-2-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(F)C=C(Cl)C=C1Cl MVHWKYHDYCGNQN-UHFFFAOYSA-N 0.000 description 1
- ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 description 1
- DHYXNIKICPUXJI-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-(2,4-difluorophenyl)-5-oxo-n-propan-2-yl-1,2,4-triazole-4-carboxamide Chemical compound C=1C=C(F)C=C(F)C=1N(C(C)C)C(=O)N(C1=O)C=NN1C1=CC=C(Cl)C=C1Cl DHYXNIKICPUXJI-UHFFFAOYSA-N 0.000 description 1
- PYCINWWWERDNKE-UHFFFAOYSA-N 1-(2-chloro-6-propylimidazo[1,2-b]pyridazin-3-yl)sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound N12N=C(CCC)C=CC2=NC(Cl)=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 PYCINWWWERDNKE-UHFFFAOYSA-N 0.000 description 1
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- RURQAJURNPMSSK-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3-{[2-(4-ethoxyphenyl)-3,3,3-trifluoropropoxy]methyl}benzene Chemical compound C1=CC(OCC)=CC=C1C(C(F)(F)F)COCC1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 RURQAJURNPMSSK-UHFFFAOYSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- IAQLCKZJGNTRDO-UHFFFAOYSA-N 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)F)CC1 IAQLCKZJGNTRDO-UHFFFAOYSA-N 0.000 description 1
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
- GHLCSCRDVVEUQD-UHFFFAOYSA-N 1-({1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl}oxy)ethyl methyl carbonate Chemical compound CCN1N=CC(C(=O)C=2C(=C(OCCOC)C(=CC=2)S(C)(=O)=O)C)=C1OC(C)OC(=O)OC GHLCSCRDVVEUQD-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- 239000005969 1-Methyl-cyclopropene Substances 0.000 description 1
- 239000005970 1-Naphthylacetamide Substances 0.000 description 1
- HVQHXBNMBZJPLK-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-methylprop-2-en-1-yl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound CC(=C)CNC1=C([S+]([O-])C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl HVQHXBNMBZJPLK-UHFFFAOYSA-N 0.000 description 1
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- IXWKBUKANTXHJH-UHFFFAOYSA-N 1-[5-chloro-2-methyl-4-(5-methyl-5,6-dihydro-1,4,2-dioxazin-3-yl)pyrazol-3-yl]sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=C(Cl)C=2C=2OC(C)CON=2)C)=N1 IXWKBUKANTXHJH-UHFFFAOYSA-N 0.000 description 1
- FLEFKKUZMDEUIP-QFIPXVFZSA-N 1-[6-[(5s)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]spiro[1h-2-benzofuran-3,3'-azetidine]-1'-yl]-2-methylsulfonylethanone Chemical compound C1N(C(=O)CS(=O)(=O)C)CC21C1=CC=C(C=3C[C@](ON=3)(C=3C=C(Cl)C(F)=C(Cl)C=3)C(F)(F)F)C=C1CO2 FLEFKKUZMDEUIP-QFIPXVFZSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- LDKSCZJUIURGMW-UHFFFAOYSA-N 1-isothiocyanato-3-methylsulfanylpropane Chemical group CSCCCN=C=S LDKSCZJUIURGMW-UHFFFAOYSA-N 0.000 description 1
- BXKKQFGRMSOANI-UHFFFAOYSA-N 1-methoxy-3-[4-[(2-methoxy-2,4,4-trimethyl-3h-chromen-7-yl)oxy]phenyl]-1-methylurea Chemical compound C1=CC(NC(=O)N(C)OC)=CC=C1OC1=CC=C2C(C)(C)CC(C)(OC)OC2=C1 BXKKQFGRMSOANI-UHFFFAOYSA-N 0.000 description 1
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 1
- 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 1
- SHDPRTQPPWIEJG-UHFFFAOYSA-N 1-methylcyclopropene Chemical compound CC1=CC1 SHDPRTQPPWIEJG-UHFFFAOYSA-N 0.000 description 1
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 1
- XFNJVKMNNVCYEK-UHFFFAOYSA-N 1-naphthaleneacetamide Chemical compound C1=CC=C2C(CC(=O)N)=CC=CC2=C1 XFNJVKMNNVCYEK-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Chemical class CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- ANBOMSJGDBBKMR-UHFFFAOYSA-N 11-Dodecenyl acetate Chemical compound CC(=O)OCCCCCCCCCCC=C ANBOMSJGDBBKMR-UHFFFAOYSA-N 0.000 description 1
- YJINQJFQLQIYHX-PLNGDYQASA-N 11Z-Tetradecenyl acetate Chemical compound CC\C=C/CCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-PLNGDYQASA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical class NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 description 1
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 1
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
- 239000002794 2,4-DB Substances 0.000 description 1
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- NIOPZPCMRQGZCE-WEVVVXLNSA-N 2,4-dinitro-6-(octan-2-yl)phenyl (E)-but-2-enoate Chemical compound CCCCCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)\C=C\C NIOPZPCMRQGZCE-WEVVVXLNSA-N 0.000 description 1
- PSOZMUMWCXLRKX-UHFFFAOYSA-N 2,4-dinitro-6-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O PSOZMUMWCXLRKX-UHFFFAOYSA-N 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- KGKGSIUWJCAFPX-UHFFFAOYSA-N 2,6-dichlorothiobenzamide Chemical compound NC(=S)C1=C(Cl)C=CC=C1Cl KGKGSIUWJCAFPX-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
- BDQWWOHKFDSADC-UHFFFAOYSA-N 2-(2,4-dichloro-3-methylphenoxy)-n-phenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C)OC1=CC=C(Cl)C(C)=C1Cl BDQWWOHKFDSADC-UHFFFAOYSA-N 0.000 description 1
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 1
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
- PTQBEFQWTBZMED-UHFFFAOYSA-N 2-(3-ethylsulfonylpyridin-2-yl)-5-(trifluoromethylsulfonyl)-1,3-benzoxazole Chemical group CCS(=O)(=O)C1=CC=CN=C1C1=NC2=CC(S(=O)(=O)C(F)(F)F)=CC=C2O1 PTQBEFQWTBZMED-UHFFFAOYSA-N 0.000 description 1
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 description 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- KWLVWJPJKJMCSH-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide Chemical compound C1=C(OCC#C)C(OC)=CC(CCNC(=O)C(OCC#C)C=2C=CC(Cl)=CC=2)=C1 KWLVWJPJKJMCSH-UHFFFAOYSA-N 0.000 description 1
- YABFPHSQTSFWQB-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(1,2,4-triazol-1-yl)-3-(trimethylsilyl)propan-2-ol Chemical compound C=1C=C(F)C=CC=1C(O)(C[Si](C)(C)C)CN1C=NC=N1 YABFPHSQTSFWQB-UHFFFAOYSA-N 0.000 description 1
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 1
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 1
- NGLCOYIAJMJYQI-UHFFFAOYSA-N 2-(4-methoxyiminocyclohexyl)-2-(3,3,3-trifluoropropylsulfonyl)acetonitrile Chemical compound CON=C1CCC(C(C#N)S(=O)(=O)CCC(F)(F)F)CC1 NGLCOYIAJMJYQI-UHFFFAOYSA-N 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- DSABESMCWFGGNQ-UHFFFAOYSA-N 2-(ethoxymethyl)-4,6-dinitrophenol Chemical compound CCOCC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O DSABESMCWFGGNQ-UHFFFAOYSA-N 0.000 description 1
- PGOOBECODWQEAB-FIBGUPNXSA-N 2-[(2-chloro-1,3-thiazol-5-yl)methyl]-1-nitro-3-(trideuteriomethyl)guanidine Chemical compound [2H]C([2H])([2H])NC(N[N+]([O-])=O)=NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-FIBGUPNXSA-N 0.000 description 1
- YXBDMGSFNUJTBR-NFSGWXFISA-N 2-[(E)-N-[(E)-3-chloroprop-2-enoxy]-C-propylcarbonimidoyl]-5-(2-ethylsulfanylpropyl)-3-hydroxycyclohex-2-en-1-one Chemical compound Cl/C=C/CO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O YXBDMGSFNUJTBR-NFSGWXFISA-N 0.000 description 1
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 1
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 description 1
- ANQRDMDBJYHVII-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazine-4-carbonyl]cyclohexane-1,3-dione Chemical compound COC=1C=C(C=CC=1OC)N1N=C(C=C(C1=O)C(=O)C1C(CCCC1=O)=O)C ANQRDMDBJYHVII-UHFFFAOYSA-N 0.000 description 1
- BOTNFCTYKJBUMU-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-4-ium-1-yl]-2-oxoacetate Chemical compound CC(C)C[NH+]1CCN(C(=O)C([O-])=O)CC1 BOTNFCTYKJBUMU-UHFFFAOYSA-N 0.000 description 1
- JERZEQUMJNCPRJ-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=C(C(F)(F)F)C=1C(O)(C)CN1C=NC=N1 JERZEQUMJNCPRJ-UHFFFAOYSA-N 0.000 description 1
- SIIJJFOXEOHODQ-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=C(C(F)(F)F)C=1C(O)(C(C)C)CN1C=NC=N1 SIIJJFOXEOHODQ-UHFFFAOYSA-N 0.000 description 1
- BSFAVVHPEZCASB-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1 BSFAVVHPEZCASB-UHFFFAOYSA-N 0.000 description 1
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 1
- IQWMUTFHGXREBR-UHFFFAOYSA-N 2-[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3-yl)-2,4-dichlorophenoxy]acetonitrile Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#N)=C(Cl)C=C1Cl IQWMUTFHGXREBR-UHFFFAOYSA-N 0.000 description 1
- ONNQFZOZHDEENE-UHFFFAOYSA-N 2-[5-(but-3-yn-2-yloxy)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione Chemical compound C1=C(Cl)C(OC(C)C#C)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F ONNQFZOZHDEENE-UHFFFAOYSA-N 0.000 description 1
- KPSTXQYTZBZXMM-UHFFFAOYSA-N 2-[8-chloro-4-(4-methoxyphenyl)-3-oxoquinoxaline-2-carbonyl]cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C(=O)C2C(CCCC2=O)=O)=NC2=C(Cl)C=CC=C21 KPSTXQYTZBZXMM-UHFFFAOYSA-N 0.000 description 1
- IOYNQIMAUDJVEI-ZFNPBRLTSA-N 2-[N-[(E)-3-chloroprop-2-enoxy]-C-ethylcarbonimidoyl]-3-hydroxy-5-(oxan-4-yl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOC\C=C\Cl)CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-ZFNPBRLTSA-N 0.000 description 1
- VQRYVKJGEDNMNC-UHFFFAOYSA-N 2-[[2-chloro-3-[2-(1,3-dioxolan-2-yl)ethoxy]-4-methylsulfonylphenyl]-hydroxymethylidene]cyclohexane-1,3-dione Chemical compound ClC1=C(OCCC2OCCO2)C(S(=O)(=O)C)=CC=C1C(O)=C1C(=O)CCCC1=O VQRYVKJGEDNMNC-UHFFFAOYSA-N 0.000 description 1
- WUZNHSBFPPFULJ-UHFFFAOYSA-N 2-[[4-chloro-6-(cyclopropylamino)-1,3,5-triazin-2-yl]amino]-2-methylpropanenitrile Chemical compound N#CC(C)(C)NC1=NC(Cl)=NC(NC2CC2)=N1 WUZNHSBFPPFULJ-UHFFFAOYSA-N 0.000 description 1
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical class NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- KWNGIKVZXFFZNN-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;4-methylbenzenesulfonate Chemical compound C[N+]1=CC=CC=C1Cl.CC1=CC=C(S([O-])(=O)=O)C=C1 KWNGIKVZXFFZNN-UHFFFAOYSA-M 0.000 description 1
- QCTALYCTVMUWPT-UHFFFAOYSA-N 2-chloro-3-(4-chlorophenyl)propanoic acid Chemical compound OC(=O)C(Cl)CC1=CC=C(Cl)C=C1 QCTALYCTVMUWPT-UHFFFAOYSA-N 0.000 description 1
- SOEFVBXUNROUOX-UHFFFAOYSA-N 2-chloro-5-fluorobenzaldehyde Chemical compound FC1=CC=C(Cl)C(C=O)=C1 SOEFVBXUNROUOX-UHFFFAOYSA-N 0.000 description 1
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 description 1
- OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 1
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
- KZNDFYDURHAESM-UHFFFAOYSA-N 2-chloro-n-(2-ethyl-6-methylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(COC(C)C)C(=O)CCl KZNDFYDURHAESM-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- ZDOOQPFIGYHZFV-UHFFFAOYSA-N 2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane Chemical compound O1C(CC)OCC1COC(C=C1)=CC=C1OC1=CC=CC=C1 ZDOOQPFIGYHZFV-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- AWSZRJQNBMEZOI-UHFFFAOYSA-N 2-methoxyethyl 2-(4-tert-butylphenyl)-2-cyano-3-oxo-3-[2-(trifluoromethyl)phenyl]propanoate Chemical compound C=1C=C(C(C)(C)C)C=CC=1C(C#N)(C(=O)OCCOC)C(=O)C1=CC=CC=C1C(F)(F)F AWSZRJQNBMEZOI-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- JFJWVJAVVIQZRT-UHFFFAOYSA-N 2-phenyl-1,3-dihydropyrazole Chemical class C1C=CNN1C1=CC=CC=C1 JFJWVJAVVIQZRT-UHFFFAOYSA-N 0.000 description 1
- DDKSOYXZEXYSGJ-UHFFFAOYSA-N 2-phenyloxadiazolidin-4-one Chemical class N1C(=O)CON1C1=CC=CC=C1 DDKSOYXZEXYSGJ-UHFFFAOYSA-N 0.000 description 1
- PDPWCKVFIFAQIQ-UHFFFAOYSA-N 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide Chemical compound CNC(=O)C(OC)C1=CC=CC=C1COC1=CC(C)=CC=C1C PDPWCKVFIFAQIQ-UHFFFAOYSA-N 0.000 description 1
- UFAPVJDEYHLLBG-UHFFFAOYSA-N 2-{2-chloro-4-(methylsulfonyl)-3-[(tetrahydrofuran-2-ylmethoxy)methyl]benzoyl}cyclohexane-1,3-dione Chemical compound ClC1=C(COCC2OCCC2)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O UFAPVJDEYHLLBG-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 1
- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- SOUGWDPPRBKJEX-UHFFFAOYSA-N 3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical compound ClCC(=O)C(C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- GSNZNZUNAJCHDO-UHFFFAOYSA-N 3-(4-bromophenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=C(Br)C=C1 GSNZNZUNAJCHDO-UHFFFAOYSA-N 0.000 description 1
- XCGBHLLWJZOLEM-UHFFFAOYSA-N 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide Chemical compound CC1CC(C)(C)C(C(=CC=2)F)=C1C=2NC(=O)C1=CN(C)N=C1C(F)F XCGBHLLWJZOLEM-UHFFFAOYSA-N 0.000 description 1
- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 1
- DGOAXBPOVUPPEB-UHFFFAOYSA-N 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]pyrazole-4-carboxamide Chemical compound C=1N(C)N=C(C(F)F)C=1C(=O)N(OC)C(C)CC1=C(Cl)C=C(Cl)C=C1Cl DGOAXBPOVUPPEB-UHFFFAOYSA-N 0.000 description 1
- QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical class OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 0.000 description 1
- CUTZZBQQGUIEGT-UHFFFAOYSA-N 3-[(3,4-dichloro-1,2-thiazol-5-yl)methoxy]-1,2-benzothiazole 1,1-dioxide Chemical compound ClC1=NSC(COC=2C3=CC=CC=C3S(=O)(=O)N=2)=C1Cl CUTZZBQQGUIEGT-UHFFFAOYSA-N 0.000 description 1
- YFEUKKUPOVGUIW-UHFFFAOYSA-N 3-[3-chloro-4-[chloro(difluoro)methyl]sulfanylphenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=C(SC(F)(F)Cl)C(Cl)=C1 YFEUKKUPOVGUIW-UHFFFAOYSA-N 0.000 description 1
- AMVYOVYGIJXTQB-UHFFFAOYSA-N 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(NC(=O)N(C)C)C=C1 AMVYOVYGIJXTQB-UHFFFAOYSA-N 0.000 description 1
- CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 description 1
- RAMUASXTSSXCMB-UHFFFAOYSA-N 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide Chemical compound C1CC1C(C)NC(=O)C1=CC(Cl)=CC(Br)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl RAMUASXTSSXCMB-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- RUXHWBMJNBBYNL-UHFFFAOYSA-N 3-hydroxy-1,2-dihydropyrrol-5-one Chemical class OC1=CC(=O)NC1 RUXHWBMJNBBYNL-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- AITONNZGADUAJV-UHFFFAOYSA-N 3-phenyl-4h-triazol-5-one Chemical class N1=NC(=O)CN1C1=CC=CC=C1 AITONNZGADUAJV-UHFFFAOYSA-N 0.000 description 1
- XWSSUYOEOWLFEI-UHFFFAOYSA-N 3-phenylpyridazine Chemical class C1=CC=CC=C1C1=CC=CN=N1 XWSSUYOEOWLFEI-UHFFFAOYSA-N 0.000 description 1
- SWTPIYGGSMJRTB-UHFFFAOYSA-N 4,4-difluoro-3,3-dimethyl-1-quinolin-3-ylisoquinoline Chemical compound C12=CC=CC=C2C(F)(F)C(C)(C)N=C1C1=CN=C(C=CC=C2)C2=C1 SWTPIYGGSMJRTB-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- LABQLTFAPITERI-UHFFFAOYSA-N 4-(1-but-2-ynoxyethyl)-1,2-dimethoxybenzene Chemical compound COC1=CC=C(C(C)OCC#CC)C=C1OC LABQLTFAPITERI-UHFFFAOYSA-N 0.000 description 1
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 1
- QDFVXXBCJYNKKC-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-cyclopropylbutyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1CCCC(C=1C=CC(Cl)=CC=1)C1CC1 QDFVXXBCJYNKKC-UHFFFAOYSA-N 0.000 description 1
- BPFUIWLQXNPZHI-UHFFFAOYSA-N 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-N-[(methoxyamino)methylidene]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)N\C=N/OC)=CC=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)C1 BPFUIWLQXNPZHI-UHFFFAOYSA-N 0.000 description 1
- OXDDDHGGRFRLEE-UHFFFAOYSA-N 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1-carboxamide Chemical compound C12=CC=CC=C2C(C(=O)NCC(=O)NCC(F)(F)F)=CC=C1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(C(F)(F)F)=C1 OXDDDHGGRFRLEE-UHFFFAOYSA-N 0.000 description 1
- ADZSGNDOZREKJK-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-ethylsulfanyl-1,2,4-triazin-5-one Chemical compound CCSC1=NN=C(C(C)(C)C)C(=O)N1N ADZSGNDOZREKJK-UHFFFAOYSA-N 0.000 description 1
- NBTRAUIPMWUAHA-UHFFFAOYSA-N 4-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazole-5-carboxylic acid Chemical compound CC(C)(C)OC(=O)Nc1nc(Cl)c(s1)C(O)=O NBTRAUIPMWUAHA-UHFFFAOYSA-N 0.000 description 1
- LHZOTJOOBRODLL-UHFFFAOYSA-N 4-oxo-1-(pyrimidin-5-ylmethyl)-3-[3-(trifluoromethyl)phenyl]pyrido[1,2-a]pyrimidin-5-ium-2-olate Chemical compound O=C1[N+]2=CC=CC=C2N(CC=2C=NC=NC=2)C([O-])=C1C1=CC=CC(C(F)(F)F)=C1 LHZOTJOOBRODLL-UHFFFAOYSA-N 0.000 description 1
- NYRMIJKDBAQCHC-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one Chemical compound O1C(NC)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 NYRMIJKDBAQCHC-UHFFFAOYSA-N 0.000 description 1
- OPEJGICLTMWFNQ-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methoxymethyl]-5-methyl-3-(3-methylthiophen-2-yl)-4h-1,2-oxazole Chemical compound C1=CSC(C=2CC(C)(COCC=3C(=CC=CC=3F)F)ON=2)=C1C OPEJGICLTMWFNQ-UHFFFAOYSA-N 0.000 description 1
- SOZRVJLJEGLPGH-UHFFFAOYSA-N 5-[2-chloro-6-(5-chloropyrimidin-2-yl)oxyphenyl]-3-(difluoromethyl)-1,2-oxazole Chemical compound ClC=1C=NC(=NC=1)OC1=C(C(=CC=C1)Cl)C1=CC(=NO1)C(F)F SOZRVJLJEGLPGH-UHFFFAOYSA-N 0.000 description 1
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 1
- ODNZLRLWXRXPOH-UHFFFAOYSA-N 5-amino-4-bromo-2-phenylpyridazin-3-one Chemical compound O=C1C(Br)=C(N)C=NN1C1=CC=CC=C1 ODNZLRLWXRXPOH-UHFFFAOYSA-N 0.000 description 1
- RIKRAZXJZVPXNZ-UHFFFAOYSA-N 5-bromo-2-(3-chloropyridin-2-yl)-N-[4,6-dichloro-3-fluoro-2-(methylcarbamoyl)phenyl]pyrazole-3-carboxamide Chemical compound CNC(=O)C1=C(C(=CC(=C1F)Cl)Cl)NC(=O)C2=CC(=NN2C3=C(C=CC=N3)Cl)Br RIKRAZXJZVPXNZ-UHFFFAOYSA-N 0.000 description 1
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
- NRTLIYOWLVMQBO-UHFFFAOYSA-N 5-chloro-1,3-dimethyl-N-(1,1,3-trimethyl-1,3-dihydro-2-benzofuran-4-yl)pyrazole-4-carboxamide Chemical compound C=12C(C)OC(C)(C)C2=CC=CC=1NC(=O)C=1C(C)=NN(C)C=1Cl NRTLIYOWLVMQBO-UHFFFAOYSA-N 0.000 description 1
- GOFJDXZZHFNFLV-UHFFFAOYSA-N 5-fluoro-1,3-dimethyl-N-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(F)N(C)N=C1C GOFJDXZZHFNFLV-UHFFFAOYSA-N 0.000 description 1
- KVUHRPLZWABERU-UHFFFAOYSA-N 5-fluoro-4-imino-3-methyl-1-(4-methylphenyl)sulfonylpyrimidin-2-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(=O)N(C)C(=N)C(F)=C1 KVUHRPLZWABERU-UHFFFAOYSA-N 0.000 description 1
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 1
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 1
- QHXDTLYEHWXDSO-UHFFFAOYSA-N 6-chloro-2-n,2-n,4-n,4-n-tetraethyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(Cl)=NC(N(CC)CC)=N1 QHXDTLYEHWXDSO-UHFFFAOYSA-N 0.000 description 1
- OOHIAOSLOGDBCE-UHFFFAOYSA-N 6-chloro-4-n-cyclopropyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC(Cl)=NC(NC2CC2)=N1 OOHIAOSLOGDBCE-UHFFFAOYSA-N 0.000 description 1
- LJGZUMNXGLDTFF-UHFFFAOYSA-N 6-tert-butyl-3-methyl-2,4-dinitrophenol Chemical compound CC1=C([N+]([O-])=O)C=C(C(C)(C)C)C(O)=C1[N+]([O-])=O LJGZUMNXGLDTFF-UHFFFAOYSA-N 0.000 description 1
- MZTLOILRKLUURT-QPEQYQDCSA-N 6-tert-butyl-4-[(z)-2-methylpropylideneamino]-3-methylsulfanyl-1,2,4-triazin-5-one Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1\N=C/C(C)C MZTLOILRKLUURT-QPEQYQDCSA-N 0.000 description 1
- VSVKOUBCDZYAQY-UHFFFAOYSA-N 7-chloro-1,2-benzothiazole Chemical compound ClC1=CC=CC2=C1SN=C2 VSVKOUBCDZYAQY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UHYISDCXHNDRHZ-UHFFFAOYSA-N 7h-[1,3]thiazolo[5,4-e]benzotriazole Chemical class C1=CC2=NCSC2=C2N=NN=C21 UHYISDCXHNDRHZ-UHFFFAOYSA-N 0.000 description 1
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- GSAAJQNJNPBBSX-WAYWQWQTSA-N 9Z-Tetradecen-1-ol Chemical compound CCCC\C=C/CCCCCCCCO GSAAJQNJNPBBSX-WAYWQWQTSA-N 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 240000004507 Abelmoschus esculentus Species 0.000 description 1
- 239000005651 Acequinocyl Substances 0.000 description 1
- 239000005875 Acetamiprid Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 1
- 239000002890 Aclonifen Substances 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 244000295724 Allium chinense Species 0.000 description 1
- 235000016790 Allium chinense Nutrition 0.000 description 1
- 240000002234 Allium sativum Species 0.000 description 1
- 235000001270 Allium sibiricum Nutrition 0.000 description 1
- 239000005877 Alpha-Cypermethrin Substances 0.000 description 1
- 241001149961 Alternaria brassicae Species 0.000 description 1
- 241001157812 Alternaria brassicicola Species 0.000 description 1
- 241000212254 Alternaria porri Species 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000005726 Ametoctradin Substances 0.000 description 1
- 239000003666 Amidosulfuron Substances 0.000 description 1
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 description 1
- 239000005468 Aminopyralid Substances 0.000 description 1
- 239000005727 Amisulbrom Substances 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 description 1
- 241000172143 Aphanomyces cochlioides Species 0.000 description 1
- 244000309619 Aphanomyces raphani Species 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 241000205585 Aquilegia canadensis 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
- 244000003416 Asparagus officinalis Species 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 239000005878 Azadirachtin Substances 0.000 description 1
- 239000005469 Azimsulfuron Substances 0.000 description 1
- AFIIBUOYKYSPKB-UHFFFAOYSA-N Aziprotryne Chemical compound CSC1=NC(NC(C)C)=NC(N=[N+]=[N-])=N1 AFIIBUOYKYSPKB-UHFFFAOYSA-N 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000193388 Bacillus thuringiensis Species 0.000 description 1
- 241000193363 Bacillus thuringiensis serovar aizawai Species 0.000 description 1
- 241000193365 Bacillus thuringiensis serovar israelensis Species 0.000 description 1
- 241000609114 Bacillus thuringiensis serovar japonensis Species 0.000 description 1
- 241001147758 Bacillus thuringiensis serovar kurstaki Species 0.000 description 1
- 241000193369 Bacillus thuringiensis serovar tenebrionis Species 0.000 description 1
- 239000005734 Benalaxyl Substances 0.000 description 1
- 239000005735 Benalaxyl-M Substances 0.000 description 1
- 239000005471 Benfluralin Substances 0.000 description 1
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 description 1
- 239000005472 Bensulfuron methyl Substances 0.000 description 1
- RRNIZKPFKNDSRS-UHFFFAOYSA-N Bensulide Chemical compound CC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1 RRNIZKPFKNDSRS-UHFFFAOYSA-N 0.000 description 1
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 description 1
- 239000005737 Benzovindiflupyr Substances 0.000 description 1
- DTCJYIIKPVRVDD-UHFFFAOYSA-N Benzthiazuron Chemical compound C1=CC=C2SC(NC(=O)NC)=NC2=C1 DTCJYIIKPVRVDD-UHFFFAOYSA-N 0.000 description 1
- 239000005884 Beta-Cyfluthrin Substances 0.000 description 1
- 239000005653 Bifenazate Substances 0.000 description 1
- 239000005484 Bifenox Substances 0.000 description 1
- 239000005874 Bifenthrin Substances 0.000 description 1
- 241001465178 Bipolaris Species 0.000 description 1
- 239000005738 Bixafen Substances 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 101000742062 Bos taurus Protein phosphatase 1G Proteins 0.000 description 1
- 239000005740 Boscalid Substances 0.000 description 1
- 241000190146 Botryosphaeria Species 0.000 description 1
- 241000499339 Botrytis allii Species 0.000 description 1
- 241000994684 Botrytis byssoidea Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 241000004822 Botrytis tulipae Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- IXVMHGVQKLDRKH-VRESXRICSA-N Brassinolide Natural products O=C1OC[C@@H]2[C@@H]3[C@@](C)([C@H]([C@@H]([C@@H](O)[C@H](O)[C@H](C(C)C)C)C)CC3)CC[C@@H]2[C@]2(C)[C@@H]1C[C@H](O)[C@H](O)C2 IXVMHGVQKLDRKH-VRESXRICSA-N 0.000 description 1
- XTFNPKDYCLFGPV-OMCISZLKSA-N Bromofenoxim Chemical compound C1=C(Br)C(O)=C(Br)C=C1\C=N\OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O XTFNPKDYCLFGPV-OMCISZLKSA-N 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- 239000005741 Bromuconazole Substances 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- OEYOMNZEMCPTKN-UHFFFAOYSA-N Butamifos Chemical compound CCC(C)NP(=S)(OCC)OC1=CC(C)=CC=C1[N+]([O-])=O OEYOMNZEMCPTKN-UHFFFAOYSA-N 0.000 description 1
- SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 description 1
- ZOGDSYNXUXQGHF-XIEYBQDHSA-N Butroxydim Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(\C(CC)=N\OCC)=C(O)C2)=C1C ZOGDSYNXUXQGHF-XIEYBQDHSA-N 0.000 description 1
- BYYMILHAKOURNM-UHFFFAOYSA-N Buturon Chemical compound C#CC(C)N(C)C(=O)NC1=CC=C(Cl)C=C1 BYYMILHAKOURNM-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- HVROXNRRBUDHGY-LHQOWCCASA-N C(CCCCCCC\C=C/C=C/CC)CC(=O)O.C(C)(=O)OCCCCCCCC\C=C/C=C/CC Chemical compound C(CCCCCCC\C=C/C=C/CC)CC(=O)O.C(C)(=O)OCCCCCCCC\C=C/C=C/CC HVROXNRRBUDHGY-LHQOWCCASA-N 0.000 description 1
- TZSGBCBQGCHMEM-BHNLCIIOSA-N C(CCCCCCC\C=C/CCCC)CC(=O)O.C(C)(=O)OCCCCCCCC\C=C/CCCC Chemical compound C(CCCCCCC\C=C/CCCC)CC(=O)O.C(C)(=O)OCCCCCCCC\C=C/CCCC TZSGBCBQGCHMEM-BHNLCIIOSA-N 0.000 description 1
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 240000008384 Capsicum annuum var. annuum Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 239000005490 Carbetamide Substances 0.000 description 1
- 239000005746 Carboxin Substances 0.000 description 1
- 239000005492 Carfentrazone-ethyl Substances 0.000 description 1
- 241000219321 Caryophyllaceae Species 0.000 description 1
- 235000003301 Ceiba pentandra Nutrition 0.000 description 1
- 244000146553 Ceiba pentandra Species 0.000 description 1
- 241001619326 Cephalosporium Species 0.000 description 1
- 241000530549 Cercospora beticola Species 0.000 description 1
- DXXVCXKMSWHGTF-UHFFFAOYSA-N Chlomethoxyfen Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 DXXVCXKMSWHGTF-UHFFFAOYSA-N 0.000 description 1
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 1
- VCBRBUKGTWLJOB-UHFFFAOYSA-N Chloranocryl Chemical compound CC(=C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 VCBRBUKGTWLJOB-UHFFFAOYSA-N 0.000 description 1
- 239000005886 Chlorantraniliprole Substances 0.000 description 1
- NLYNUTMZTCLNOO-UHFFFAOYSA-N Chlorbromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C(Cl)=C1 NLYNUTMZTCLNOO-UHFFFAOYSA-N 0.000 description 1
- ULBXWWGWDPVHAO-UHFFFAOYSA-N Chlorbufam Chemical compound C#CC(C)OC(=O)NC1=CC=CC(Cl)=C1 ULBXWWGWDPVHAO-UHFFFAOYSA-N 0.000 description 1
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 1
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OUDYXRYNDPEKLK-XNTDXEJSSA-N Chloromebuform Chemical compound CCCCN(C)\C=N\C1=CC=C(Cl)C=C1C OUDYXRYNDPEKLK-XNTDXEJSSA-N 0.000 description 1
- IBZZDPVVVSNQOY-UHFFFAOYSA-N Chloromethiuron Chemical compound CN(C)C(=S)NC1=CC=C(Cl)C=C1C IBZZDPVVVSNQOY-UHFFFAOYSA-N 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 239000005494 Chlorotoluron Substances 0.000 description 1
- 239000005647 Chlorpropham Substances 0.000 description 1
- 239000005945 Chlorpyrifos-methyl Substances 0.000 description 1
- 239000005496 Chlorsulfuron Substances 0.000 description 1
- 239000005887 Chromafenozide Substances 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 241000186650 Clavibacter Species 0.000 description 1
- 239000005497 Clethodim Substances 0.000 description 1
- 239000005654 Clofentezine Substances 0.000 description 1
- 239000005499 Clomazone Substances 0.000 description 1
- 239000005500 Clopyralid Substances 0.000 description 1
- 239000005888 Clothianidin Substances 0.000 description 1
- 241001133184 Colletotrichum agaves Species 0.000 description 1
- 241000407098 Colletotrichum coffeanum Species 0.000 description 1
- 241000152100 Colletotrichum horii Species 0.000 description 1
- 241000222235 Colletotrichum orbiculare Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000004035 Cryptotaenia japonica Nutrition 0.000 description 1
- 244000146493 Cryptotaenia japonica Species 0.000 description 1
- 101710151559 Crystal protein Proteins 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 description 1
- 239000005889 Cyantraniliprole Substances 0.000 description 1
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 description 1
- 239000005501 Cycloxydim Substances 0.000 description 1
- 239000005655 Cyflumetofen Substances 0.000 description 1
- 239000005502 Cyhalofop-butyl Substances 0.000 description 1
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 description 1
- 239000005756 Cymoxanil Substances 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- FMGYKKMPNATWHP-UHFFFAOYSA-N Cyperquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=CC=C1 FMGYKKMPNATWHP-UHFFFAOYSA-N 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 239000005758 Cyprodinil Substances 0.000 description 1
- KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical compound ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 description 1
- 239000005891 Cyromazine Substances 0.000 description 1
- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical group COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
- 239000005644 Dazomet Substances 0.000 description 1
- BIQOEDQVNIYWPQ-UHFFFAOYSA-N Delachlor Chemical compound CC(C)COCN(C(=O)CCl)C1=C(C)C=CC=C1C BIQOEDQVNIYWPQ-UHFFFAOYSA-N 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 239000005503 Desmedipham Substances 0.000 description 1
- 241001508802 Diaporthe Species 0.000 description 1
- 241001645342 Diaporthe citri Species 0.000 description 1
- 241001373666 Diaporthe sp. Species 0.000 description 1
- 239000005504 Dicamba Substances 0.000 description 1
- QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 description 1
- 241000555695 Didymella Species 0.000 description 1
- 241001273467 Didymella pinodes Species 0.000 description 1
- LWLJUMBEZJHXHV-UHFFFAOYSA-N Dienochlor Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C1(Cl)C1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LWLJUMBEZJHXHV-UHFFFAOYSA-N 0.000 description 1
- WFKSADNZWSKCRZ-UHFFFAOYSA-N Diethatyl-ethyl Chemical group CCOC(=O)CN(C(=O)CCl)C1=C(CC)C=CC=C1CC WFKSADNZWSKCRZ-UHFFFAOYSA-N 0.000 description 1
- 239000005759 Diethofencarb Substances 0.000 description 1
- 239000005760 Difenoconazole Substances 0.000 description 1
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- 239000005507 Diflufenican Substances 0.000 description 1
- DHWRNDJOGMTCPB-UHFFFAOYSA-N Dimefuron Chemical compound ClC1=CC(NC(=O)N(C)C)=CC=C1N1C(=O)OC(C(C)(C)C)=N1 DHWRNDJOGMTCPB-UHFFFAOYSA-N 0.000 description 1
- 239000005508 Dimethachlor Substances 0.000 description 1
- IKYICRRUVNIHPP-UHFFFAOYSA-N Dimethametryn Chemical compound CCNC1=NC(NC(C)C(C)C)=NC(SC)=N1 IKYICRRUVNIHPP-UHFFFAOYSA-N 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- OFDYMSKSGFSLLM-UHFFFAOYSA-N Dinitramine Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O OFDYMSKSGFSLLM-UHFFFAOYSA-N 0.000 description 1
- IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-UHFFFAOYSA-N 0.000 description 1
- 235000011511 Diospyros Nutrition 0.000 description 1
- 241000723267 Diospyros Species 0.000 description 1
- QAHFOPIILNICLA-UHFFFAOYSA-N Diphenamid Chemical compound C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1 QAHFOPIILNICLA-UHFFFAOYSA-N 0.000 description 1
- 241000461780 Diplocarpon Species 0.000 description 1
- NPWMZOGDXOFZIN-UHFFFAOYSA-N Dipropetryn Chemical compound CCSC1=NC(NC(C)C)=NC(NC(C)C)=N1 NPWMZOGDXOFZIN-UHFFFAOYSA-N 0.000 description 1
- 239000005630 Diquat Substances 0.000 description 1
- 239000005764 Dithianon Substances 0.000 description 1
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- 239000005766 Dodine Substances 0.000 description 1
- AIGRXSNSLVJMEA-UHFFFAOYSA-N EPN Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-UHFFFAOYSA-N 0.000 description 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
- 241000125117 Elsinoe Species 0.000 description 1
- 241000901048 Elsinoe ampelina Species 0.000 description 1
- 241000125118 Elsinoe fawcettii Species 0.000 description 1
- 239000005767 Epoxiconazole Substances 0.000 description 1
- 235000009008 Eriobotrya japonica Nutrition 0.000 description 1
- 244000061508 Eriobotrya japonica Species 0.000 description 1
- 239000005895 Esfenvalerate Substances 0.000 description 1
- BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 description 1
- PTFJIKYUEPWBMS-UHFFFAOYSA-N Ethalfluralin Chemical compound CC(=C)CN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O PTFJIKYUEPWBMS-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005976 Ethephon Substances 0.000 description 1
- FNELVJVBIYMIMC-UHFFFAOYSA-N Ethiprole Chemical compound N1=C(C#N)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FNELVJVBIYMIMC-UHFFFAOYSA-N 0.000 description 1
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 description 1
- 239000005897 Etoxazole Substances 0.000 description 1
- FGIWFCGDPUIBEZ-UHFFFAOYSA-N Etrimfos Chemical compound CCOC1=CC(OP(=S)(OC)OC)=NC(CC)=N1 FGIWFCGDPUIBEZ-UHFFFAOYSA-N 0.000 description 1
- 241000221997 Exobasidium Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 239000005772 Famoxadone Substances 0.000 description 1
- 239000005774 Fenamidone Substances 0.000 description 1
- 239000005958 Fenamiphos (aka phenamiphos) Substances 0.000 description 1
- 239000005656 Fenazaquin Substances 0.000 description 1
- 239000005775 Fenbuconazole Substances 0.000 description 1
- 239000005776 Fenhexamid Substances 0.000 description 1
- ZLSWBLPERHFHIS-UHFFFAOYSA-N Fenoprop Chemical compound OC(=O)C(C)OC1=CC(Cl)=C(Cl)C=C1Cl ZLSWBLPERHFHIS-UHFFFAOYSA-N 0.000 description 1
- HMIBKHHNXANVHR-UHFFFAOYSA-N Fenothiocarb Chemical compound CN(C)C(=O)SCCCCOC1=CC=CC=C1 HMIBKHHNXANVHR-UHFFFAOYSA-N 0.000 description 1
- PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 description 1
- 239000005898 Fenoxycarb Substances 0.000 description 1
- 239000005777 Fenpropidin Substances 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- 239000005779 Fenpyrazamine Substances 0.000 description 1
- 239000005657 Fenpyroximate Substances 0.000 description 1
- WHWHBAUZDPEHEM-UHFFFAOYSA-N Fenthiaprop Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2S1 WHWHBAUZDPEHEM-UHFFFAOYSA-N 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 description 1
- 239000005899 Fipronil Substances 0.000 description 1
- 239000005514 Flazasulfuron Substances 0.000 description 1
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 description 1
- 239000005900 Flonicamid Substances 0.000 description 1
- 239000005529 Florasulam Substances 0.000 description 1
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 239000005901 Flubendiamide Substances 0.000 description 1
- FICWGWVVIRLNRB-UHFFFAOYSA-N Flucetosulfuron Chemical compound COCC(=O)OC(C(C)F)C1=NC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 FICWGWVVIRLNRB-UHFFFAOYSA-N 0.000 description 1
- MNFMIVVPXOGUMX-UHFFFAOYSA-N Fluchloralin Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MNFMIVVPXOGUMX-UHFFFAOYSA-N 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- 239000005531 Flufenacet Substances 0.000 description 1
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 1
- IRECWLYBCAZIJM-UHFFFAOYSA-N Flumiclorac pentyl Chemical group C1=C(Cl)C(OCC(=O)OCCCCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F IRECWLYBCAZIJM-UHFFFAOYSA-N 0.000 description 1
- 239000005533 Fluometuron Substances 0.000 description 1
- 239000005782 Fluopicolide Substances 0.000 description 1
- 239000005783 Fluopyram Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- HHMCAJWVGYGUEF-UHFFFAOYSA-N Fluorodifen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O HHMCAJWVGYGUEF-UHFFFAOYSA-N 0.000 description 1
- 239000005784 Fluoxastrobin Substances 0.000 description 1
- AOQMRUTZEYVDIL-UHFFFAOYSA-N Flupoxam Chemical compound C=1C=C(Cl)C(COCC(F)(F)C(F)(F)F)=CC=1N1N=C(C(=O)N)N=C1C1=CC=CC=C1 AOQMRUTZEYVDIL-UHFFFAOYSA-N 0.000 description 1
- PXRROZVNOOEPPZ-UHFFFAOYSA-N Flupropanate Chemical compound OC(=O)C(F)(F)C(F)F PXRROZVNOOEPPZ-UHFFFAOYSA-N 0.000 description 1
- 239000005785 Fluquinconazole Substances 0.000 description 1
- YWBVHLJPRPCRSD-UHFFFAOYSA-N Fluridone Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC=C1 YWBVHLJPRPCRSD-UHFFFAOYSA-N 0.000 description 1
- 239000005535 Flurochloridone Substances 0.000 description 1
- 239000005558 Fluroxypyr Substances 0.000 description 1
- 239000005559 Flurtamone Substances 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 239000005787 Flutriafol Substances 0.000 description 1
- 239000005788 Fluxapyroxad Substances 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 description 1
- 239000005959 Fosthiazate Substances 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- ULCWZQJLFZEXCS-KGLIPLIRSA-N Furconazole-cis Chemical compound O1[C@@H](OCC(F)(F)F)CC[C@@]1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 ULCWZQJLFZEXCS-KGLIPLIRSA-N 0.000 description 1
- 241000221778 Fusarium fujikuroi Species 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 239000005903 Gamma-cyhalothrin Substances 0.000 description 1
- 229930191978 Gibberellin Natural products 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 239000005564 Halosulfuron methyl Substances 0.000 description 1
- FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical group ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 description 1
- CAWXEEYDBZRFPE-UHFFFAOYSA-N Hexazinone Chemical compound O=C1N(C)C(N(C)C)=NC(=O)N1C1CCCCC1 CAWXEEYDBZRFPE-UHFFFAOYSA-N 0.000 description 1
- 239000005661 Hexythiazox Substances 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 241000549404 Hyaloperonospora parasitica Species 0.000 description 1
- 239000005795 Imazalil Substances 0.000 description 1
- 239000005566 Imazamox Substances 0.000 description 1
- 239000005981 Imazaquin Substances 0.000 description 1
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 1
- PPCUNNLZTNMXFO-ACCUITESSA-N Imicyafos Chemical compound CCCSP(=O)(OCC)N1CCN(CC)\C1=N/C#N PPCUNNLZTNMXFO-ACCUITESSA-N 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- PMAAYIYCDXGUAP-UHFFFAOYSA-N Indanofan Chemical compound O=C1C2=CC=CC=C2C(=O)C1(CC)CC1(C=2C=C(Cl)C=CC=2)CO1 PMAAYIYCDXGUAP-UHFFFAOYSA-N 0.000 description 1
- 239000005907 Indoxacarb Substances 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 239000005797 Iprovalicarb Substances 0.000 description 1
- PSYBGEADHLUXCS-UHFFFAOYSA-N Isocil Chemical compound CC(C)N1C(=O)NC(C)=C(Br)C1=O PSYBGEADHLUXCS-UHFFFAOYSA-N 0.000 description 1
- 239000005798 Isofetamid Substances 0.000 description 1
- NEKOXWSIMFDGMA-UHFFFAOYSA-N Isopropalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(C)C)C=C1[N+]([O-])=O NEKOXWSIMFDGMA-UHFFFAOYSA-N 0.000 description 1
- 239000005799 Isopyrazam Substances 0.000 description 1
- JLLJHQLUZAKJFH-UHFFFAOYSA-N Isouron Chemical compound CN(C)C(=O)NC=1C=C(C(C)(C)C)ON=1 JLLJHQLUZAKJFH-UHFFFAOYSA-N 0.000 description 1
- 239000005570 Isoxaben Substances 0.000 description 1
- 239000005571 Isoxaflutole Substances 0.000 description 1
- ANFHKXSOSRDDRQ-UHFFFAOYSA-N Isoxapyrifop Chemical compound C1CCON1C(=O)C(C)OC(C=C1)=CC=C1OC1=NC=C(Cl)C=C1Cl ANFHKXSOSRDDRQ-UHFFFAOYSA-N 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FAIXYKHYOGVFKA-UHFFFAOYSA-N Kinetin Natural products N=1C=NC=2N=CNC=2C=1N(C)C1=CC=CO1 FAIXYKHYOGVFKA-UHFFFAOYSA-N 0.000 description 1
- 239000005800 Kresoxim-methyl Substances 0.000 description 1
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 description 1
- 239000005572 Lenacil Substances 0.000 description 1
- 241000228457 Leptosphaeria maculans Species 0.000 description 1
- 241000191880 Lettuce big-vein associated varicosavirus Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- 239000005573 Linuron Substances 0.000 description 1
- 239000005912 Lufenuron Substances 0.000 description 1
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 239000005575 MCPB Substances 0.000 description 1
- 101150039283 MCPB gene Proteins 0.000 description 1
- 241000584607 Macrospora Species 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 239000005803 Mandestrobin Substances 0.000 description 1
- 239000005804 Mandipropamid Substances 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-UHFFFAOYSA-N 0.000 description 1
- 239000005805 Mepanipyrim Substances 0.000 description 1
- 239000005806 Meptyldinocap Substances 0.000 description 1
- 239000005578 Mesotrione Substances 0.000 description 1
- 239000005914 Metaflumizone Substances 0.000 description 1
- MIFOMMKAVSCNKQ-HWIUFGAZSA-N Metaflumizone Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N\N=C(C=1C=C(C=CC=1)C(F)(F)F)\CC1=CC=C(C#N)C=C1 MIFOMMKAVSCNKQ-HWIUFGAZSA-N 0.000 description 1
- 239000005807 Metalaxyl Substances 0.000 description 1
- 239000005808 Metalaxyl-M Substances 0.000 description 1
- 239000005956 Metaldehyde Substances 0.000 description 1
- 101710150834 Metallocarboxypeptidase A Proteins 0.000 description 1
- 239000002169 Metam Substances 0.000 description 1
- 239000005579 Metamitron Substances 0.000 description 1
- 239000005580 Metazachlor Substances 0.000 description 1
- 239000005868 Metconazole Substances 0.000 description 1
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 1
- 239000005916 Methomyl Substances 0.000 description 1
- DDUIUBPJPOKOMV-UHFFFAOYSA-N Methoprotryne Chemical compound COCCCNC1=NC(NC(C)C)=NC(SC)=N1 DDUIUBPJPOKOMV-UHFFFAOYSA-N 0.000 description 1
- 239000005917 Methoxyfenozide Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FMINYZXVCTYSNY-UHFFFAOYSA-N Methyldymron Chemical compound C=1C=CC=CC=1N(C)C(=O)NC(C)(C)C1=CC=CC=C1 FMINYZXVCTYSNY-UHFFFAOYSA-N 0.000 description 1
- 239000005809 Metiram Substances 0.000 description 1
- 239000005581 Metobromuron Substances 0.000 description 1
- WLFDQEVORAMCIM-UHFFFAOYSA-N Metobromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C=C1 WLFDQEVORAMCIM-UHFFFAOYSA-N 0.000 description 1
- 239000005582 Metosulam Substances 0.000 description 1
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 1
- 239000005810 Metrafenone Substances 0.000 description 1
- 239000005583 Metribuzin Substances 0.000 description 1
- 239000005918 Milbemectin Substances 0.000 description 1
- KXGYBSNVFXBPNO-UHFFFAOYSA-N Monalide Chemical compound CCCC(C)(C)C(=O)NC1=CC=C(Cl)C=C1 KXGYBSNVFXBPNO-UHFFFAOYSA-N 0.000 description 1
- 241001518731 Monilinia fructicola Species 0.000 description 1
- 241001363493 Monilinia mali Species 0.000 description 1
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 description 1
- 241000218231 Moraceae Species 0.000 description 1
- LVPGGWVHPIAEMC-UHFFFAOYSA-L Morfamquat Chemical compound [Cl-].[Cl-].CC1COCC(C)N1C(=O)C[N+]1=CC=C(C=2C=C[N+](CC(=O)N3C(COCC3C)C)=CC=2)C=C1 LVPGGWVHPIAEMC-UHFFFAOYSA-L 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 241000234615 Musaceae Species 0.000 description 1
- 239000005811 Myclobutanil Substances 0.000 description 1
- 241001433116 Mycosphaerella nawae Species 0.000 description 1
- 241000633856 Mycosphaerella pomi Species 0.000 description 1
- WXZVAROIGSFCFJ-UHFFFAOYSA-N N,N-diethyl-2-(naphthalen-1-yloxy)propanamide Chemical compound C1=CC=C2C(OC(C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-UHFFFAOYSA-N 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- IUOKJNROJISWRO-UHFFFAOYSA-N N-(2-cyano-3-methylbutan-2-yl)-2-(2,4-dichlorophenoxy)propanamide Chemical compound CC(C)C(C)(C#N)NC(=O)C(C)OC1=CC=C(Cl)C=C1Cl IUOKJNROJISWRO-UHFFFAOYSA-N 0.000 description 1
- IEKSGOPPBDNFFP-UHFFFAOYSA-N N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound FC1=C(C=CC=C1)NC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O IEKSGOPPBDNFFP-UHFFFAOYSA-N 0.000 description 1
- BZRUVKZGXNSXMB-UHFFFAOYSA-N N-(butan-2-yl)-6-chloro-N'-ethyl-1,3,5-triazine-2,4-diamine Chemical compound CCNC1=NC(Cl)=NC(NC(C)CC)=N1 BZRUVKZGXNSXMB-UHFFFAOYSA-N 0.000 description 1
- ZJMZZNVGNSWOOM-UHFFFAOYSA-N N-(butan-2-yl)-N'-ethyl-6-methoxy-1,3,5-triazine-2,4-diamine Chemical compound CCNC1=NC(NC(C)CC)=NC(OC)=N1 ZJMZZNVGNSWOOM-UHFFFAOYSA-N 0.000 description 1
- FHFBSBQYPLFMHC-TURZUDJPSA-N N-[(2Z)-2-[2-chloro-4-(2-cyclopropylethynyl)phenyl]-2-propan-2-yloxyiminoethyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)O\N=C(/CNC(=O)c1cn(C)nc1C(F)F)c1ccc(cc1Cl)C#CC1CC1 FHFBSBQYPLFMHC-TURZUDJPSA-N 0.000 description 1
- IUFUITYPUYMIHI-UHFFFAOYSA-N N-[1-(3,5-dimethylphenoxy)propan-2-yl]-6-(2-fluoropropan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N)=NC(C(C)(C)F)=NC=1NC(C)COC1=CC(C)=CC(C)=C1 IUFUITYPUYMIHI-UHFFFAOYSA-N 0.000 description 1
- CCCGEKHKTPTUHJ-UHFFFAOYSA-N N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC2=C1C1CCC2C1=C(Cl)Cl CCCGEKHKTPTUHJ-UHFFFAOYSA-N 0.000 description 1
- NQRFDNJEBWAUBL-UHFFFAOYSA-N N-[cyano(2-thienyl)methyl]-4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NCC)=NC(CC)=C1C(=O)NC(C#N)C1=CC=CS1 NQRFDNJEBWAUBL-UHFFFAOYSA-N 0.000 description 1
- NTBVTCXMRYKRTB-UHFFFAOYSA-N N-{2-[(4,6-dimethoxypyrimidin-2-yl)(hydroxy)methyl]-6-(methoxymethyl)phenyl}-1,1-difluoromethanesulfonamide Chemical compound COCC1=CC=CC(C(O)C=2N=C(OC)C=C(OC)N=2)=C1NS(=O)(=O)C(F)F NTBVTCXMRYKRTB-UHFFFAOYSA-N 0.000 description 1
- XQJQCBDIXRIYRP-UHFFFAOYSA-N N-{2-[1,1'-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-1-methyl-1pyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1C(C2CC2)C1 XQJQCBDIXRIYRP-UHFFFAOYSA-N 0.000 description 1
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 description 1
- 239000005585 Napropamide Substances 0.000 description 1
- CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 239000005586 Nicosulfuron Substances 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- UMKANAFDOQQUKE-UHFFFAOYSA-N Nitralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O UMKANAFDOQQUKE-UHFFFAOYSA-N 0.000 description 1
- 241001668536 Oculimacula yallundae Species 0.000 description 1
- 241000896238 Oidium Species 0.000 description 1
- 241000207836 Olea <angiosperm> Species 0.000 description 1
- 241000207834 Oleaceae Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241001219479 Olpidium Species 0.000 description 1
- 241000177754 Olpidium virulentus Species 0.000 description 1
- 239000005587 Oryzalin Substances 0.000 description 1
- 239000005588 Oxadiazon Substances 0.000 description 1
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 239000005950 Oxamyl Substances 0.000 description 1
- 239000005589 Oxasulfuron Substances 0.000 description 1
- 239000005812 Oxathiapiprolin Substances 0.000 description 1
- FCOHEOSCARXMMS-UHFFFAOYSA-N Oxaziclomefone Chemical compound C1OC(C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C1=CC(Cl)=CC(Cl)=C1 FCOHEOSCARXMMS-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- 239000005590 Oxyfluorfen Substances 0.000 description 1
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- CDHBAZHPEVDWMO-UHFFFAOYSA-N Parafluron Chemical compound CN(C)C(=O)NC1=CC=C(C(F)(F)F)C=C1 CDHBAZHPEVDWMO-UHFFFAOYSA-N 0.000 description 1
- 241000736122 Parastagonospora nodorum Species 0.000 description 1
- 241000222291 Passalora fulva Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- SGEJQUSYQTVSIU-UHFFFAOYSA-N Pebulate Chemical compound CCCCN(CC)C(=O)SCCC SGEJQUSYQTVSIU-UHFFFAOYSA-N 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 239000005814 Pencycuron Substances 0.000 description 1
- 239000005591 Pendimethalin Substances 0.000 description 1
- 239000005815 Penflufen Substances 0.000 description 1
- 239000005592 Penoxsulam Substances 0.000 description 1
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 description 1
- WGVWLKXZBUVUAM-UHFFFAOYSA-N Pentanochlor Chemical compound CCCC(C)C(=O)NC1=CC=C(C)C(Cl)=C1 WGVWLKXZBUVUAM-UHFFFAOYSA-N 0.000 description 1
- 239000005816 Penthiopyrad Substances 0.000 description 1
- WHTBVLXUSXVMEV-UHFFFAOYSA-N Perfluidone Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 WHTBVLXUSXVMEV-UHFFFAOYSA-N 0.000 description 1
- 241000751661 Peronospora belbahrii Species 0.000 description 1
- 241001670201 Peronospora destructor Species 0.000 description 1
- 241000118319 Peronospora effusa Species 0.000 description 1
- 241001670203 Peronospora manshurica Species 0.000 description 1
- 244000062780 Petroselinum sativum Species 0.000 description 1
- 241000440444 Phakopsora Species 0.000 description 1
- 241000682645 Phakopsora pachyrhizi Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- PWEOEHNGYFXZLI-UHFFFAOYSA-N Phenisopham Chemical compound C=1C=CC=CC=1N(CC)C(=O)OC1=CC=CC(NC(=O)OC(C)C)=C1 PWEOEHNGYFXZLI-UHFFFAOYSA-N 0.000 description 1
- 239000005594 Phenmedipham Substances 0.000 description 1
- 241001503951 Phoma Species 0.000 description 1
- 241001557902 Phomopsis sp. Species 0.000 description 1
- 239000005921 Phosmet Substances 0.000 description 1
- 241001270527 Phyllosticta citrullina Species 0.000 description 1
- 241000471406 Physoderma maydis Species 0.000 description 1
- 241001149949 Phytophthora cactorum Species 0.000 description 1
- 241000263678 Phytophthora cactorum var. applanata Species 0.000 description 1
- 241000233637 Phytophthora palmivora Species 0.000 description 1
- 241000626604 Phytophthora porri Species 0.000 description 1
- 241000948155 Phytophthora sojae Species 0.000 description 1
- 241001026374 Phytophthora vignae f. sp. adzukicola Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 239000005595 Picloram Substances 0.000 description 1
- 239000005596 Picolinafen Substances 0.000 description 1
- 239000005818 Picoxystrobin Substances 0.000 description 1
- 239000005597 Pinoxaden Substances 0.000 description 1
- 241000758706 Piperaceae Species 0.000 description 1
- UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 description 1
- 239000005923 Pirimicarb Substances 0.000 description 1
- 239000005924 Pirimiphos-methyl Substances 0.000 description 1
- 241001503436 Plasmodiophora brassicae Species 0.000 description 1
- 241001505682 Plasmopara nivea 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
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000132152 Polymyxa Species 0.000 description 1
- 229930182764 Polyoxin Natural products 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 description 1
- 101710099847 Probable metallocarboxypeptidase A Proteins 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- RSVPPPHXAASNOL-UHFFFAOYSA-N Prodiamine Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O RSVPPPHXAASNOL-UHFFFAOYSA-N 0.000 description 1
- ITVQAKZNYJEWKS-UHFFFAOYSA-N Profluralin Chemical compound [O-][N+](=O)C=1C=C(C(F)(F)F)C=C([N+]([O-])=O)C=1N(CCC)CC1CC1 ITVQAKZNYJEWKS-UHFFFAOYSA-N 0.000 description 1
- 239000005599 Profoxydim Substances 0.000 description 1
- IPDFPNNPBMREIF-CHWSQXEVSA-N Prohydrojasmon Chemical compound CCCCC[C@@H]1[C@@H](CC(=O)OCCC)CCC1=O IPDFPNNPBMREIF-CHWSQXEVSA-N 0.000 description 1
- MKIMSXGUTQTKJU-UHFFFAOYSA-N Propamocarb hydrochloride Chemical compound [Cl-].CCCOC(=O)NCCC[NH+](C)C MKIMSXGUTQTKJU-UHFFFAOYSA-N 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 239000005823 Propineb Substances 0.000 description 1
- 239000005602 Propyzamide Substances 0.000 description 1
- 239000005824 Proquinazid Substances 0.000 description 1
- 239000005603 Prosulfocarb Substances 0.000 description 1
- 239000005604 Prosulfuron Substances 0.000 description 1
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 1
- 239000005825 Prothioconazole Substances 0.000 description 1
- 240000005809 Prunus persica Species 0.000 description 1
- 241000184297 Pseudocercospora musae Species 0.000 description 1
- 241000386899 Pseudocercospora vitis Species 0.000 description 1
- 241000682843 Pseudocercosporella Species 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 241000342307 Pseudoperonospora humuli Species 0.000 description 1
- 241001123561 Puccinia coronata Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 241001123583 Puccinia striiformis Species 0.000 description 1
- 206010037549 Purpura Diseases 0.000 description 1
- 241001672981 Purpura Species 0.000 description 1
- 239000005925 Pymetrozine Substances 0.000 description 1
- IHHMUBRVTJMLQO-UHFFFAOYSA-N Pyraclonil Chemical compound C#CCN(C)C1=C(C#N)C=NN1C1=NN(CCCC2)C2=C1Cl IHHMUBRVTJMLQO-UHFFFAOYSA-N 0.000 description 1
- 239000005869 Pyraclostrobin Substances 0.000 description 1
- 239000005605 Pyraflufen-ethyl Substances 0.000 description 1
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 description 1
- 241000228454 Pyrenophora graminea Species 0.000 description 1
- 241000520648 Pyrenophora teres Species 0.000 description 1
- 239000005663 Pyridaben Substances 0.000 description 1
- 239000005926 Pyridalyl Substances 0.000 description 1
- 239000005606 Pyridate Substances 0.000 description 1
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 description 1
- RRKHIAYNPVQKEF-UHFFFAOYSA-N Pyriftalid Chemical compound COC1=CC(OC)=NC(SC=2C=3C(=O)OC(C)C=3C=CC=2)=N1 RRKHIAYNPVQKEF-UHFFFAOYSA-N 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- 239000005829 Pyriofenone Substances 0.000 description 1
- MWMQNVGAHVXSPE-UHFFFAOYSA-N Pyriprole Chemical compound ClC=1C=C(C(F)(F)F)C=C(Cl)C=1N1N=C(C#N)C(SC(F)F)=C1NCC1=CC=CC=N1 MWMQNVGAHVXSPE-UHFFFAOYSA-N 0.000 description 1
- 239000005927 Pyriproxyfen Substances 0.000 description 1
- CNILNQMBAHKMFS-UHFFFAOYSA-M Pyrithiobac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C([O-])=O)=N1 CNILNQMBAHKMFS-UHFFFAOYSA-M 0.000 description 1
- 239000005607 Pyroxsulam Substances 0.000 description 1
- 235000001630 Pyrus pyrifolia var culta Nutrition 0.000 description 1
- 244000079529 Pyrus serotina Species 0.000 description 1
- 241001622911 Pythium graminicola Species 0.000 description 1
- 241000202873 Pythium iwayamai Species 0.000 description 1
- 241000342339 Pythium ultimum var. ultimum Species 0.000 description 1
- 241000870867 Pythium zingiberis Species 0.000 description 1
- 239000005608 Quinmerac Substances 0.000 description 1
- OBLNWSCLAYSJJR-UHFFFAOYSA-N Quinoclamin Chemical compound C1=CC=C2C(=O)C(N)=C(Cl)C(=O)C2=C1 OBLNWSCLAYSJJR-UHFFFAOYSA-N 0.000 description 1
- 239000002167 Quinoclamine Substances 0.000 description 1
- 239000005831 Quinoxyfen Substances 0.000 description 1
- 108091030071 RNAI Proteins 0.000 description 1
- 241001421802 Ramularia grevilleana Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 241001515786 Rhynchosporium Species 0.000 description 1
- 241001515790 Rhynchosporium secalis Species 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 241001638069 Rigidoporus microporus Species 0.000 description 1
- 239000005616 Rimsulfuron Substances 0.000 description 1
- 241001107098 Rubiaceae Species 0.000 description 1
- 229930001406 Ryanodine Natural products 0.000 description 1
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 1
- WOZQBERUBLYCEG-UHFFFAOYSA-N SWEP Chemical compound COC(=O)NC1=CC=C(Cl)C(Cl)=C1 WOZQBERUBLYCEG-UHFFFAOYSA-N 0.000 description 1
- 241000342317 Sclerospora Species 0.000 description 1
- 241001518705 Sclerotinia minor Species 0.000 description 1
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
- 241001136641 Sclerotinia trifoliorum Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 239000005834 Sedaxane Substances 0.000 description 1
- 241000407146 Septogloeum Species 0.000 description 1
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 1
- 241000332749 Setosphaeria turcica Species 0.000 description 1
- JXVIIQLNUPXOII-UHFFFAOYSA-N Siduron Chemical compound CC1CCCCC1NC(=O)NC1=CC=CC=C1 JXVIIQLNUPXOII-UHFFFAOYSA-N 0.000 description 1
- 239000005835 Silthiofam Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920000142 Sodium polycarboxylate Polymers 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 239000005929 Spinetoram Substances 0.000 description 1
- GOENIMGKWNZVDA-OAMCMWGQSA-N Spinetoram Chemical compound CO[C@@H]1[C@H](OCC)[C@@H](OC)[C@H](C)O[C@H]1OC1C[C@H]2[C@@H]3C=C4C(=O)[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@H](CC5)N(C)C)CCC[C@H](CC)OC(=O)CC4[C@@H]3CC[C@@H]2C1 GOENIMGKWNZVDA-OAMCMWGQSA-N 0.000 description 1
- 239000005930 Spinosad Substances 0.000 description 1
- 239000005664 Spirodiclofen Substances 0.000 description 1
- 239000005665 Spiromesifen Substances 0.000 description 1
- 239000005931 Spirotetramat Substances 0.000 description 1
- 239000005837 Spiroxamine Substances 0.000 description 1
- 241000397423 Spongospora subterranea f. sp. subterranea Species 0.000 description 1
- 241001406921 Squamosa Species 0.000 description 1
- 241000533281 Stagonospora Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000005618 Sulcotrione Substances 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
- 239000005619 Sulfosulfuron Substances 0.000 description 1
- 239000005934 Sulfoxaflor Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000005937 Tebufenozide Substances 0.000 description 1
- 239000005658 Tebufenpyrad Substances 0.000 description 1
- HBPDKDSFLXWOAE-UHFFFAOYSA-N Tebuthiuron Chemical compound CNC(=O)N(C)C1=NN=C(C(C)(C)C)S1 HBPDKDSFLXWOAE-UHFFFAOYSA-N 0.000 description 1
- 239000005938 Teflubenzuron Substances 0.000 description 1
- 239000005939 Tefluthrin Substances 0.000 description 1
- 239000005620 Tembotrione Substances 0.000 description 1
- NBQCNZYJJMBDKY-UHFFFAOYSA-N Terbacil Chemical compound CC=1NC(=O)N(C(C)(C)C)C(=O)C=1Cl NBQCNZYJJMBDKY-UHFFFAOYSA-N 0.000 description 1
- 239000005621 Terbuthylazine Substances 0.000 description 1
- 239000005840 Tetraconazole Substances 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 239000005940 Thiacloprid Substances 0.000 description 1
- 239000005941 Thiamethoxam Substances 0.000 description 1
- BBJPZPLAZVZTGR-UHFFFAOYSA-N Thiazafluron Chemical compound CNC(=O)N(C)C1=NN=C(C(F)(F)F)S1 BBJPZPLAZVZTGR-UHFFFAOYSA-N 0.000 description 1
- YIJZJEYQBAAWRJ-UHFFFAOYSA-N Thiazopyr Chemical compound N1=C(C(F)F)C(C(=O)OC)=C(CC(C)C)C(C=2SCCN=2)=C1C(F)(F)F YIJZJEYQBAAWRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005623 Thifensulfuron-methyl Substances 0.000 description 1
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 239000005843 Thiram Substances 0.000 description 1
- 241000722133 Tilletia Species 0.000 description 1
- PHSUVQBHRAWOQD-UHFFFAOYSA-N Tiocarbazil Chemical compound CCC(C)N(C(C)CC)C(=O)SCC1=CC=CC=C1 PHSUVQBHRAWOQD-UHFFFAOYSA-N 0.000 description 1
- 239000005845 Tolclofos-methyl Substances 0.000 description 1
- 239000005624 Tralkoxydim Substances 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 239000005625 Tri-allate Substances 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
- 239000005846 Triadimenol Substances 0.000 description 1
- 241000894120 Trichoderma atroviride Species 0.000 description 1
- 239000005627 Triclopyr Substances 0.000 description 1
- IBZHOAONZVJLOB-UHFFFAOYSA-N Tridiphane Chemical compound ClC1=CC(Cl)=CC(C2(CC(Cl)(Cl)Cl)OC2)=C1 IBZHOAONZVJLOB-UHFFFAOYSA-N 0.000 description 1
- HFBWPRKWDIRYNX-UHFFFAOYSA-N Trietazine Chemical compound CCNC1=NC(Cl)=NC(N(CC)CC)=N1 HFBWPRKWDIRYNX-UHFFFAOYSA-N 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- 239000005858 Triflumizole Substances 0.000 description 1
- 239000005942 Triflumuron Substances 0.000 description 1
- 239000005859 Triticonazole Substances 0.000 description 1
- 239000005629 Tritosulfuron Substances 0.000 description 1
- 241000722921 Tulipa gesneriana Species 0.000 description 1
- 241000959260 Typhula Species 0.000 description 1
- 241000333201 Typhula incarnata Species 0.000 description 1
- 241000983470 Typhula ishikariensis Species 0.000 description 1
- 241000510929 Uncinula Species 0.000 description 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- 241000007070 Ustilago nuda Species 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- 239000005860 Valifenalate Substances 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
- 241000405217 Viola <butterfly> Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- CVQODEWAPZVVBU-UHFFFAOYSA-N XMC Chemical compound CNC(=O)OC1=CC(C)=CC(C)=C1 CVQODEWAPZVVBU-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000005863 Zoxamide Substances 0.000 description 1
- 241001360088 Zymoseptoria tritici Species 0.000 description 1
- GBAWQJNHVWMTLU-RQJHMYQMSA-N [(1R,5S)-7-chloro-6-bicyclo[3.2.0]hepta-2,6-dienyl] dimethyl phosphate Chemical compound C1=CC[C@@H]2C(OP(=O)(OC)OC)=C(Cl)[C@@H]21 GBAWQJNHVWMTLU-RQJHMYQMSA-N 0.000 description 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
- AMRQXHFXNZFDCH-SECBINFHSA-N [(2r)-1-(ethylamino)-1-oxopropan-2-yl] n-phenylcarbamate Chemical compound CCNC(=O)[C@@H](C)OC(=O)NC1=CC=CC=C1 AMRQXHFXNZFDCH-SECBINFHSA-N 0.000 description 1
- ZZGJZGSVLNSDPG-JZATWXMZSA-N [(9Z)-tetradeca-9,12-dienyl] acetate Chemical compound CC=CC\C=C/CCCCCCCCOC(C)=O ZZGJZGSVLNSDPG-JZATWXMZSA-N 0.000 description 1
- QQODLKZGRKWIFG-RUTXASTPSA-N [(R)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-RUTXASTPSA-N 0.000 description 1
- KAATUXNTWXVJKI-QPIRBTGLSA-N [(s)-cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-QPIRBTGLSA-N 0.000 description 1
- FSAVDKDHPDSCTO-WQLSENKSSA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl FSAVDKDHPDSCTO-WQLSENKSSA-N 0.000 description 1
- QSGNQELHULIMSJ-POHAHGRESA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] dimethyl phosphate Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl QSGNQELHULIMSJ-POHAHGRESA-N 0.000 description 1
- BTKXLQSCEOHKTF-SREVYHEPSA-N [(z)-hexadec-11-enyl] acetate Chemical compound CCCC\C=C/CCCCCCCCCCOC(C)=O BTKXLQSCEOHKTF-SREVYHEPSA-N 0.000 description 1
- KVIZNNVXXNFLMU-AIIUZBJTSA-N [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1r,3r)-2,2-dimethyl-3-[(e)-prop-1-enyl]cyclopropane-1-carboxylate Chemical class FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)[C@H]1C(C)(C)[C@@H]1\C=C\C KVIZNNVXXNFLMU-AIIUZBJTSA-N 0.000 description 1
- DPJITPZADZSLBP-PIPQINALSA-N [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1r,3r)-3-[(e)-2-cyanoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)[C@H]1C(C)(C)[C@@H]1\C=C(/C)C#N DPJITPZADZSLBP-PIPQINALSA-N 0.000 description 1
- CFGPESLNPCIKIX-UHFFFAOYSA-N [2-[ethoxy(propylsulfanyl)phosphoryl]oxyphenyl] n-methylcarbamate Chemical compound CCCSP(=O)(OCC)OC1=CC=CC=C1OC(=O)NC CFGPESLNPCIKIX-UHFFFAOYSA-N 0.000 description 1
- CYDCAYZRTPOUJJ-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] n-(1-chlorobutan-2-yl)carbamate Chemical compound CCC(CCl)NC(=O)OC1=CC=CC(NC(=O)OC)=C1 CYDCAYZRTPOUJJ-UHFFFAOYSA-N 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
- WXQMIXCKKFECIU-UHFFFAOYSA-N [4-[2-chloro-3-[(3,5-dimethylpyrazol-1-yl)methyl]-4-methylsulfonylbenzoyl]-2,5-dimethylpyrazol-3-yl] 1,3-dimethylpyrazole-4-carboxylate Chemical compound CN1N=C(C(=C1)C(=O)OC1=C(C(=NN1C)C)C(C1=C(C(=C(C=C1)S(=O)(=O)C)CN1N=C(C=C1C)C)Cl)=O)C WXQMIXCKKFECIU-UHFFFAOYSA-N 0.000 description 1
- NWBFHIJKEYFVND-UHFFFAOYSA-N [4-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)benzoyl]-2-ethylpyrazol-3-yl] 1,3-dimethylpyrazole-4-carboxylate Chemical compound N1(C=C(C(=O)OC=2N(CC)N=CC=2C(=O)C2=C(C(=C(S(=O)(=O)C)C=C2)COCC(F)(F)F)Cl)C(C)=N1)C NWBFHIJKEYFVND-UHFFFAOYSA-N 0.000 description 1
- JNVCSEDACVAATK-UHFFFAOYSA-L [Ca+2].[S-]SSS[S-] Chemical compound [Ca+2].[S-]SSS[S-] JNVCSEDACVAATK-UHFFFAOYSA-L 0.000 description 1
- INISTDXBRIBGOC-CGAIIQECSA-N [cyano-(3-phenoxyphenyl)methyl] (2s)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate Chemical compound N([C@@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-CGAIIQECSA-N 0.000 description 1
- YXWCBRDRVXHABN-JCMHNJIXSA-N [cyano-(4-fluoro-3-phenoxyphenyl)methyl] 3-[(z)-2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound C=1C=C(F)C(OC=2C=CC=CC=2)=CC=1C(C#N)OC(=O)C1C(C)(C)C1\C=C(/Cl)C1=CC=C(Cl)C=C1 YXWCBRDRVXHABN-JCMHNJIXSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 229950008167 abamectin Drugs 0.000 description 1
- 230000036579 abiotic stress Effects 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- QDRXWCAVUNHOGA-UHFFFAOYSA-N acequinocyl Chemical group C1=CC=C2C(=O)C(CCCCCCCCCCCC)=C(OC(C)=O)C(=O)C2=C1 QDRXWCAVUNHOGA-UHFFFAOYSA-N 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- GDZNYEZGJAFIKA-UHFFFAOYSA-N acetoprole Chemical compound NC1=C(S(C)=O)C(C(=O)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GDZNYEZGJAFIKA-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
- DDBMQDADIHOWIC-UHFFFAOYSA-N aclonifen Chemical compound C1=C([N+]([O-])=O)C(N)=C(Cl)C(OC=2C=CC=CC=2)=C1 DDBMQDADIHOWIC-UHFFFAOYSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229960000982 afoxolaner Drugs 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 125000005282 allenyl group Chemical group 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- GGKQIOFASHYUJZ-UHFFFAOYSA-N ametoctradin Chemical compound NC1=C(CCCCCCCC)C(CC)=NC2=NC=NN21 GGKQIOFASHYUJZ-UHFFFAOYSA-N 0.000 description 1
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 description 1
- ORFPWVRKFLOQHK-UHFFFAOYSA-N amicarbazone Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- KWAIHLIXESXTJL-UHFFFAOYSA-N aminocyclopyrachlor Chemical compound OC(=O)C1=C(Cl)C(N)=NC(C2CC2)=N1 KWAIHLIXESXTJL-UHFFFAOYSA-N 0.000 description 1
- NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 description 1
- BREATYVWRHIPIY-UHFFFAOYSA-N amisulbrom Chemical compound CN(C)S(=O)(=O)N1C=NC(S(=O)(=O)N2C3=CC(F)=CC=C3C(Br)=C2C)=N1 BREATYVWRHIPIY-UHFFFAOYSA-N 0.000 description 1
- 229960002587 amitraz Drugs 0.000 description 1
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 description 1
- 150000008059 anilinopyrimidines Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 description 1
- PXWUKZGIHQRDHL-UHFFFAOYSA-N atraton Chemical compound CCNC1=NC(NC(C)C)=NC(OC)=N1 PXWUKZGIHQRDHL-UHFFFAOYSA-N 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 208000014347 autosomal dominant hyaline body myopathy Diseases 0.000 description 1
- AKNQMEBLVAMSNZ-UHFFFAOYSA-N azaconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 AKNQMEBLVAMSNZ-UHFFFAOYSA-N 0.000 description 1
- 229950000294 azaconazole Drugs 0.000 description 1
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 description 1
- XOEMATDHVZOBSG-UHFFFAOYSA-N azafenidin Chemical compound C1=C(OCC#C)C(Cl)=CC(Cl)=C1N1C(=O)N2CCCCC2=N1 XOEMATDHVZOBSG-UHFFFAOYSA-N 0.000 description 1
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 description 1
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 description 1
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- 229940097012 bacillus thuringiensis Drugs 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 1
- CJPQIRJHIZUAQP-MRXNPFEDSA-N benalaxyl-M Chemical compound CC=1C=CC=C(C)C=1N([C@H](C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-MRXNPFEDSA-N 0.000 description 1
- WQRCEBAZAUAUQC-UHFFFAOYSA-N benazolin-ethyl Chemical group C1=CC=C2SC(=O)N(CC(=O)OCC)C2=C1Cl WQRCEBAZAUAUQC-UHFFFAOYSA-N 0.000 description 1
- XEGGRYVFLWGFHI-UHFFFAOYSA-N bendiocarb Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)O2 XEGGRYVFLWGFHI-UHFFFAOYSA-N 0.000 description 1
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 1
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 1
- LJOZMWRYMKECFF-UHFFFAOYSA-N benodanil Chemical compound IC1=CC=CC=C1C(=O)NC1=CC=CC=C1 LJOZMWRYMKECFF-UHFFFAOYSA-N 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- YFXPPSKYMBTNAV-UHFFFAOYSA-N bensultap Chemical compound C=1C=CC=CC=1S(=O)(=O)SCC(N(C)C)CSS(=O)(=O)C1=CC=CC=C1 YFXPPSKYMBTNAV-UHFFFAOYSA-N 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- USRKFGIXLGKMKU-ABAIWWIYSA-N benthiavalicarb-isopropyl Chemical compound C1=C(F)C=C2SC([C@@H](C)NC(=O)[C@H](C(C)C)NC(=O)OC(C)C)=NC2=C1 USRKFGIXLGKMKU-ABAIWWIYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- HUYBEDCQLAEVPD-MNOVXSKESA-N bicyclopyrone Chemical compound COCCOCc1nc(ccc1C(=O)C1=C(O)[C@@H]2CC[C@@H](C2)C1=O)C(F)(F)F HUYBEDCQLAEVPD-MNOVXSKESA-N 0.000 description 1
- VHLKTXFWDRXILV-UHFFFAOYSA-N bifenazate Chemical compound C1=C(NNC(=O)OC(C)C)C(OC)=CC=C1C1=CC=CC=C1 VHLKTXFWDRXILV-UHFFFAOYSA-N 0.000 description 1
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 description 1
- LDLMOOXUCMHBMZ-UHFFFAOYSA-N bixafen Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=C(F)C=C1C1=CC=C(Cl)C(Cl)=C1 LDLMOOXUCMHBMZ-UHFFFAOYSA-N 0.000 description 1
- FHUKASKVKWSLCY-UHFFFAOYSA-N bixlozone Chemical compound O=C1C(C)(C)CON1CC1=CC=C(Cl)C=C1Cl FHUKASKVKWSLCY-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 229940118790 boscalid Drugs 0.000 description 1
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 1
- QSLZKWPYTWEWHC-UHFFFAOYSA-N broflanilide Chemical compound C=1C=CC(C(=O)NC=2C(=CC(=CC=2Br)C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)F)=C(F)C=1N(C)C(=O)C1=CC=CC=C1 QSLZKWPYTWEWHC-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 description 1
- HJJVPARKXDDIQD-UHFFFAOYSA-N bromuconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCC(Br)C1 HJJVPARKXDDIQD-UHFFFAOYSA-N 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- JEDYYFXHPAIBGR-UHFFFAOYSA-N butafenacil Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(Cl)C(C(=O)OC(C)(C)C(=O)OCC=C)=C1 JEDYYFXHPAIBGR-UHFFFAOYSA-N 0.000 description 1
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 description 1
- 125000006251 butylcarbonyl group Chemical group 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- KXRPCFINVWWFHQ-UHFFFAOYSA-N cadusafos Chemical compound CCC(C)SP(=O)(OCC)SC(C)CC KXRPCFINVWWFHQ-UHFFFAOYSA-N 0.000 description 1
- HFEJHAAIJZXXRE-UHFFFAOYSA-N cafenstrole Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 HFEJHAAIJZXXRE-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000010495 camellia oil Substances 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- RXDMAYSSBPYBFW-UHFFFAOYSA-N carpropamid Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C1(CC)C(C)C1(Cl)Cl RXDMAYSSBPYBFW-UHFFFAOYSA-N 0.000 description 1
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- PNCNFDRSHBFIDM-WOJGMQOQSA-N chembl111617 Chemical compound C=CCO\N=C(/CCC)C1=C(O)C(C(=O)OC)C(C)(C)CC1=O PNCNFDRSHBFIDM-WOJGMQOQSA-N 0.000 description 1
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- PSOVNZZNOMJUBI-UHFFFAOYSA-N chlorantraniliprole Chemical compound CNC(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl PSOVNZZNOMJUBI-UHFFFAOYSA-N 0.000 description 1
- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 description 1
- XQNAUQUKWRBODG-UHFFFAOYSA-N chlornitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(Cl)C=C1Cl XQNAUQUKWRBODG-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- LFHISGNCFUNFFM-UHFFFAOYSA-N chloropicrin Chemical compound [O-][N+](=O)C(Cl)(Cl)Cl LFHISGNCFUNFFM-UHFFFAOYSA-N 0.000 description 1
- RQNZCZHWQZMZER-ZLDLUXBVSA-N chloroprallethrin Chemical compound CC1=C(CC#C)C(=O)C[C@@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1C=C(Cl)Cl RQNZCZHWQZMZER-ZLDLUXBVSA-N 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
- IVUXTESCPZUGJC-UHFFFAOYSA-N chloroxuron Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1OC1=CC=C(Cl)C=C1 IVUXTESCPZUGJC-UHFFFAOYSA-N 0.000 description 1
- MJQBFSWPMMHVSM-UHFFFAOYSA-N chlorphthalim Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CCCC2)=C2C1=O MJQBFSWPMMHVSM-UHFFFAOYSA-N 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 description 1
- NNKKTZOEKDFTBU-YBEGLDIGSA-N cinidon ethyl Chemical compound C1=C(Cl)C(/C=C(\Cl)C(=O)OCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 NNKKTZOEKDFTBU-YBEGLDIGSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 description 1
- JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 description 1
- UXADOQPNKNTIHB-UHFFFAOYSA-N clofentezine Chemical compound ClC1=CC=CC=C1C1=NN=C(C=2C(=CC=CC=2)Cl)N=N1 UXADOQPNKNTIHB-UHFFFAOYSA-N 0.000 description 1
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 1
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- PZSIFLLRHQZAKV-UHFFFAOYSA-L copper;4-dodecylbenzenesulfonate;ethane-1,2-diamine Chemical compound [Cu+2].NCCN.NCCN.CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 PZSIFLLRHQZAKV-UHFFFAOYSA-L 0.000 description 1
- MMUFAGXJPKNAHT-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1 MMUFAGXJPKNAHT-UHFFFAOYSA-N 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- CWVRPJSBNHNJSI-XQNSMLJCSA-N coumoxystrobin Chemical compound C1=C2OC(=O)C(CCCC)=C(C)C2=CC=C1OCC1=CC=CC=C1\C(=C/OC)C(=O)OC CWVRPJSBNHNJSI-XQNSMLJCSA-N 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical class NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 description 1
- 150000005245 cyanopyrroles Chemical class 0.000 description 1
- DVBUIBGJRQBEDP-UHFFFAOYSA-N cyantraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl DVBUIBGJRQBEDP-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- BXIGJZDQFDFASM-UHFFFAOYSA-N cyclopyrimorate Chemical compound N=1N=C(Cl)C=C(OC(=O)N2CCOCC2)C=1OC=1C(C)=CC=CC=1C1CC1 BXIGJZDQFDFASM-UHFFFAOYSA-N 0.000 description 1
- APJLTUBHYCOZJI-VZCXRCSSSA-N cyenopyrafen Chemical compound CC1=NN(C)C(\C(OC(=O)C(C)(C)C)=C(/C#N)C=2C=CC(=CC=2)C(C)(C)C)=C1C APJLTUBHYCOZJI-VZCXRCSSSA-N 0.000 description 1
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 description 1
- 229960001591 cyfluthrin Drugs 0.000 description 1
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 description 1
- NNRSYETYEADPBW-UHFFFAOYSA-N cyhalodiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(Cl)=C1C(=O)NC(C)(C)C#N NNRSYETYEADPBW-UHFFFAOYSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 description 1
- 229950000775 cyromazine Drugs 0.000 description 1
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- WZJZMXBKUWKXTQ-UHFFFAOYSA-N desmedipham Chemical compound CCOC(=O)NC1=CC=CC(OC(=O)NC=2C=CC=CC=2)=C1 WZJZMXBKUWKXTQ-UHFFFAOYSA-N 0.000 description 1
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 150000008056 dicarboxyimides Chemical class 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 229950001327 dichlorvos Drugs 0.000 description 1
- YEJGPFZQLRMXOI-PKEIRNPWSA-N diclocymet Chemical compound N#CC(C(C)(C)C)C(=O)N[C@H](C)C1=CC=C(Cl)C=C1Cl YEJGPFZQLRMXOI-PKEIRNPWSA-N 0.000 description 1
- UWQMKVBQKFHLCE-UHFFFAOYSA-N diclomezine Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NNC(=O)C=C1 UWQMKVBQKFHLCE-UHFFFAOYSA-N 0.000 description 1
- PVDQXPBKBSCNJZ-UHFFFAOYSA-N dicloromezotiaz Chemical compound CC1=CC=C[N+](C(C(C=2C=C(Cl)C=C(Cl)C=2)=C2[O-])=O)=C1N2CC1=CN=C(Cl)S1 PVDQXPBKBSCNJZ-UHFFFAOYSA-N 0.000 description 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 description 1
- NGPMUTDCEIKKFM-UHFFFAOYSA-N dieldrin Natural products CC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl NGPMUTDCEIKKFM-UHFFFAOYSA-N 0.000 description 1
- 229950006824 dieldrin Drugs 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 229960001673 diethyltoluamide Drugs 0.000 description 1
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 description 1
- SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 1
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- FPKXBFWMIYHCID-UHFFFAOYSA-N dipymetitrone Chemical compound S1C=2C(=O)N(C)C(=O)C=2SC2=C1C(=O)N(C)C2=O FPKXBFWMIYHCID-UHFFFAOYSA-N 0.000 description 1
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- ZDXLFJGIPWQALB-UHFFFAOYSA-M disodium;oxido(oxo)borane;chlorate Chemical compound [Na+].[Na+].[O-]B=O.[O-]Cl(=O)=O ZDXLFJGIPWQALB-UHFFFAOYSA-M 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- DOFZAZXDOSGAJZ-UHFFFAOYSA-N disulfoton Chemical compound CCOP(=S)(OCC)SCCSCC DOFZAZXDOSGAJZ-UHFFFAOYSA-N 0.000 description 1
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 150000004863 dithiolanes Chemical class 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H]([NH2+]C)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960002125 enilconazole Drugs 0.000 description 1
- VMNULHCTRPXWFJ-UJSVPXBISA-N enoxastrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)\C=C\C1=CC=C(Cl)C=C1 VMNULHCTRPXWFJ-UJSVPXBISA-N 0.000 description 1
- 230000006353 environmental stress Effects 0.000 description 1
- KVIZNNVXXNFLMU-DUVUQDDDSA-N epsilon-metofluthrin Chemical class FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)[C@H]1C(C)(C)[C@@H]1\C=C/C KVIZNNVXXNFLMU-DUVUQDDDSA-N 0.000 description 1
- DPJITPZADZSLBP-DQXQJKBJSA-N epsilon-momfluorothrin Chemical compound FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)[C@H]1C(C)(C)[C@@H]1\C=C(\C)C#N DPJITPZADZSLBP-DQXQJKBJSA-N 0.000 description 1
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 description 1
- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical group CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 description 1
- HEZNVIYQEUHLNI-UHFFFAOYSA-N ethiofencarb Chemical compound CCSCC1=CC=CC=C1OC(=O)NC HEZNVIYQEUHLNI-UHFFFAOYSA-N 0.000 description 1
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- YESXTECNXIKUMM-UHFFFAOYSA-N ethyl 2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino]acetate Chemical group CCNC1=NC(Cl)=NC(NCC(=O)OCC)=N1 YESXTECNXIKUMM-UHFFFAOYSA-N 0.000 description 1
- QQADVTSTCZBBOE-UHFFFAOYSA-N ethyl 2-[[4-chloro-6-(propan-2-ylamino)-1,3,5-triazin-2-yl]amino]acetate Chemical group CCOC(=O)CNC1=NC(Cl)=NC(NC(C)C)=N1 QQADVTSTCZBBOE-UHFFFAOYSA-N 0.000 description 1
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 description 1
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical class C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 1
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 description 1
- RBWGTZRSEOIHFD-UHUFKFKFSA-N fenaminstrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1CO\N=C(/C)\C=C\C1=C(Cl)C=CC=C1Cl RBWGTZRSEOIHFD-UHUFKFKFSA-N 0.000 description 1
- ZCJPOPBZHLUFHF-UHFFFAOYSA-N fenamiphos Chemical compound CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1 ZCJPOPBZHLUFHF-UHFFFAOYSA-N 0.000 description 1
- DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 description 1
- JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 description 1
- VDLGAVXLJYLFDH-UHFFFAOYSA-N fenhexamid Chemical compound C=1C=C(O)C(Cl)=C(Cl)C=1NC(=O)C1(C)CCCCC1 VDLGAVXLJYLFDH-UHFFFAOYSA-N 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- ACDZDIIWZVQMIX-UHFFFAOYSA-N fenoxasulfone Chemical compound C1=C(Cl)C(OCC)=CC(Cl)=C1CS(=O)(=O)C1=NOC(C)(C)C1 ACDZDIIWZVQMIX-UHFFFAOYSA-N 0.000 description 1
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 description 1
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 description 1
- UTOHZQYBSYOOGC-UHFFFAOYSA-N fenpyrazamine Chemical compound O=C1N(C(C)C)N(C(=O)SCC=C)C(N)=C1C1=CC=CC=C1C UTOHZQYBSYOOGC-UHFFFAOYSA-N 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- GOWLARCWZRESHU-AQTBWJFISA-N ferimzone Chemical compound C=1C=CC=C(C)C=1C(/C)=N\NC1=NC(C)=CC(C)=N1 GOWLARCWZRESHU-AQTBWJFISA-N 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229940013764 fipronil Drugs 0.000 description 1
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 description 1
- XFZUQTKDBCOXPP-UHFFFAOYSA-N florpyrauxifen Chemical compound COC1=C(Cl)C=CC(C=2C(=C(N)C(Cl)=C(C(O)=O)N=2)F)=C1F XFZUQTKDBCOXPP-UHFFFAOYSA-N 0.000 description 1
- ATZHVIVDMUCBEY-HOTGVXAUSA-N florylpicoxamid Chemical compound C(C)(=O)OC=1C(=NC=CC=1OC)C(=O)N[C@H](C(=O)O[C@H](C(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)C)C ATZHVIVDMUCBEY-HOTGVXAUSA-N 0.000 description 1
- MXWAGQASUDSFBG-RVDMUPIBSA-N fluacrypyrim Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC(C(F)(F)F)=NC(OC(C)C)=N1 MXWAGQASUDSFBG-RVDMUPIBSA-N 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- YOWNVPAUWYHLQX-UHFFFAOYSA-N fluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 YOWNVPAUWYHLQX-UHFFFAOYSA-N 0.000 description 1
- 229950006719 fluazuron Drugs 0.000 description 1
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 1
- UOUXAYAIONPXDH-UHFFFAOYSA-M flucarbazone-sodium Chemical compound [Na+].O=C1N(C)C(OC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1OC(F)(F)F UOUXAYAIONPXDH-UHFFFAOYSA-M 0.000 description 1
- LEIWLFHGOGNSAD-UWTATZPHSA-N fluchloraminopyr Chemical compound C[C@H](C(=O)O)OC1=NC(=C(C(=C1Cl)N)Cl)F LEIWLFHGOGNSAD-UWTATZPHSA-N 0.000 description 1
- GBIHOLCMZGAKNG-CGAIIQECSA-N flucythrinate Chemical compound O=C([C@@H](C(C)C)C=1C=CC(OC(F)F)=CC=1)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 GBIHOLCMZGAKNG-CGAIIQECSA-N 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- XSNMWAPKHUGZGQ-UHFFFAOYSA-N fluensulfone Chemical compound FC(F)=C(F)CCS(=O)(=O)C1=NC=C(Cl)S1 XSNMWAPKHUGZGQ-UHFFFAOYSA-N 0.000 description 1
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 1
- GJEREQYJIQASAW-UHFFFAOYSA-N flufenerim Chemical compound CC(F)C1=NC=NC(NCCC=2C=CC(OC(F)(F)F)=CC=2)=C1Cl GJEREQYJIQASAW-UHFFFAOYSA-N 0.000 description 1
- MBHXIQDIVCJZTD-RVDMUPIBSA-N flufenoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=C(C(F)(F)F)C=C1Cl MBHXIQDIVCJZTD-RVDMUPIBSA-N 0.000 description 1
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- GBOYJIHYACSLGN-UHFFFAOYSA-N fluopicolide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CNC(=O)C1=C(Cl)C=CC=C1Cl GBOYJIHYACSLGN-UHFFFAOYSA-N 0.000 description 1
- DNJKFZQFTZJKDK-UHFFFAOYSA-N fluopimomide Chemical compound FC1=C(F)C(OC)=C(F)C(F)=C1C(=O)NCC1=NC=C(C(F)(F)F)C=C1Cl DNJKFZQFTZJKDK-UHFFFAOYSA-N 0.000 description 1
- KVDJTXBXMWJJEF-UHFFFAOYSA-N fluopyram Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CCNC(=O)C1=CC=CC=C1C(F)(F)F KVDJTXBXMWJJEF-UHFFFAOYSA-N 0.000 description 1
- UFEODZBUAFNAEU-NLRVBDNBSA-N fluoxastrobin Chemical compound C=1C=CC=C(OC=2C(=C(OC=3C(=CC=CC=3)Cl)N=CN=2)F)C=1C(=N/OC)\C1=NOCCO1 UFEODZBUAFNAEU-NLRVBDNBSA-N 0.000 description 1
- IJJVMEJXYNJXOJ-UHFFFAOYSA-N fluquinconazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(=O)C2=CC(F)=CC=C2N=C1N1C=NC=N1 IJJVMEJXYNJXOJ-UHFFFAOYSA-N 0.000 description 1
- MLBZKOGAMRTSKP-UHFFFAOYSA-N fluralaner Chemical compound C1=C(C(=O)NCC(=O)NCC(F)(F)F)C(C)=CC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 MLBZKOGAMRTSKP-UHFFFAOYSA-N 0.000 description 1
- 229960004498 fluralaner Drugs 0.000 description 1
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical compound FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 description 1
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 description 1
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
- GNVDAZSPJWCIQZ-UHFFFAOYSA-N flusulfamide Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 GNVDAZSPJWCIQZ-UHFFFAOYSA-N 0.000 description 1
- ZCNQYNHDVRPZIH-UHFFFAOYSA-N fluthiacet-methyl Chemical group C1=C(Cl)C(SCC(=O)OC)=CC(N=C2N3CCCCN3C(=O)S2)=C1F ZCNQYNHDVRPZIH-UHFFFAOYSA-N 0.000 description 1
- KGXUEPOHGFWQKF-ZCXUNETKSA-N flutianil Chemical compound COC1=CC=CC=C1N(CCS\1)C/1=C(C#N)/SC1=CC(C(F)(F)F)=CC=C1F KGXUEPOHGFWQKF-ZCXUNETKSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- SXSGXWCSHSVPGB-UHFFFAOYSA-N fluxapyroxad Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 SXSGXWCSHSVPGB-UHFFFAOYSA-N 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- DUFVKSUJRWYZQP-UHFFFAOYSA-N fosthiazate Chemical compound CCC(C)SP(=O)(OCC)N1CCSC1=O DUFVKSUJRWYZQP-UHFFFAOYSA-N 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- HAWJXYBZNNRMNO-UHFFFAOYSA-N furathiocarb Chemical compound CCCCOC(=O)N(C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 HAWJXYBZNNRMNO-UHFFFAOYSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-GCMPRSNUSA-N gamma-cyhalothrin Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-GCMPRSNUSA-N 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 230000009368 gene silencing by RNA Effects 0.000 description 1
- 238000010362 genome editing Methods 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- KKLBEFSLWYDQFI-UHFFFAOYSA-N halauxifen Chemical compound COC1=C(Cl)C=CC(C=2N=C(C(Cl)=C(N)C=2)C(O)=O)=C1F KKLBEFSLWYDQFI-UHFFFAOYSA-N 0.000 description 1
- CNKHSLKYRMDDNQ-UHFFFAOYSA-N halofenozide Chemical compound C=1C=CC=CC=1C(=O)N(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1 CNKHSLKYRMDDNQ-UHFFFAOYSA-N 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BKACAEJQMLLGAV-PLNGDYQASA-N heptafluthrin Chemical class FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)C1C(C)(C)C1\C=C/C(F)(F)F BKACAEJQMLLGAV-PLNGDYQASA-N 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- HICUREFSAIZXFQ-JOWPUVSESA-N i9z29i000j Chemical compound C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\[C@H](OC(=O)C(=N/OC)\C=1C=CC=CC=1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 HICUREFSAIZXFQ-JOWPUVSESA-N 0.000 description 1
- AGKSTYPVMZODRV-UHFFFAOYSA-N imibenconazole Chemical compound C1=CC(Cl)=CC=C1CSC(CN1N=CN=C1)=NC1=CC=C(Cl)C=C1Cl AGKSTYPVMZODRV-UHFFFAOYSA-N 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- YFONKFDEZLYQDH-BOURZNODSA-N indaziflam Chemical compound CC(F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-BOURZNODSA-N 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- YTCIYOXHHQLDEI-SNVBAGLBSA-N inpyrfluxam Chemical compound C([C@H](C=12)C)C(C)(C)C2=CC=CC=1NC(=O)C1=CN(C)N=C1C(F)F YTCIYOXHHQLDEI-SNVBAGLBSA-N 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- QTYCMDBMOLSEAM-UHFFFAOYSA-N ipconazole Chemical compound C1=NC=NN1CC1(O)C(C(C)C)CCC1CC1=CC=C(Cl)C=C1 QTYCMDBMOLSEAM-UHFFFAOYSA-N 0.000 description 1
- DSXOWZNZGWXWMX-UHFFFAOYSA-N ipflufenoquin Chemical compound CC1=NC2=C(F)C(F)=CC=C2C=C1OC1=CC=CC(F)=C1C(C)(C)O DSXOWZNZGWXWMX-UHFFFAOYSA-N 0.000 description 1
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- 125000006352 iso-propylthiomethyl group Chemical group [H]C([H])([H])C([H])(SC([H])([H])*)C([H])([H])[H] 0.000 description 1
- HOQADATXFBOEGG-UHFFFAOYSA-N isofenphos Chemical compound CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC(C)C HOQADATXFBOEGG-UHFFFAOYSA-N 0.000 description 1
- WMKZDPFZIZQROT-UHFFFAOYSA-N isofetamid Chemical compound CC1=CC(OC(C)C)=CC=C1C(=O)C(C)(C)NC(=O)C1=C(C)C=CS1 WMKZDPFZIZQROT-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- WLPCAERCXQSYLQ-UHFFFAOYSA-N isotianil Chemical compound ClC1=NSC(C(=O)NC=2C(=CC=CC=2)C#N)=C1Cl WLPCAERCXQSYLQ-UHFFFAOYSA-N 0.000 description 1
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 description 1
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 1
- 229940088649 isoxaflutole Drugs 0.000 description 1
- SDMSCIWHRZJSRN-UHFFFAOYSA-N isoxathion Chemical compound O1N=C(OP(=S)(OCC)OCC)C=C1C1=CC=CC=C1 SDMSCIWHRZJSRN-UHFFFAOYSA-N 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 229960002418 ivermectin Drugs 0.000 description 1
- ZNJFBWYDHIGLCU-HWKXXFMVSA-N jasmonic acid Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-HWKXXFMVSA-N 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- QANMHLXAZMSUEX-UHFFFAOYSA-N kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 description 1
- 229960001669 kinetin Drugs 0.000 description 1
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- 239000005910 lambda-Cyhalothrin Substances 0.000 description 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 229960000521 lufenuron Drugs 0.000 description 1
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 description 1
- GKKDCARASOJPNG-UHFFFAOYSA-N metaldehyde Chemical compound CC1OC(C)OC(C)OC(C)O1 GKKDCARASOJPNG-UHFFFAOYSA-N 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- 229950003442 methoprene Drugs 0.000 description 1
- 229930002897 methoprene Natural products 0.000 description 1
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 1
- QPTPZPIXUPELRM-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]sulfanylpropanoylamino]propanoate Chemical compound C1=C(Cl)C(SC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F QPTPZPIXUPELRM-UHFFFAOYSA-N 0.000 description 1
- KBHDSWIXRODKSZ-UHFFFAOYSA-N methyl 5-chloro-2-(trifluoromethylsulfonylamino)benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NS(=O)(=O)C(F)(F)F KBHDSWIXRODKSZ-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229920000257 metiram Polymers 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- HIIRDDUVRXCDBN-OBGWFSINSA-N metominostrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1OC1=CC=CC=C1 HIIRDDUVRXCDBN-OBGWFSINSA-N 0.000 description 1
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 1
- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- CKVMAPHTVCTEMM-ALPQRHTBSA-N milbemycin oxime Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)C(=N/O)/[C@H]3OC\2)O)C[C@H]4C1.C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)C(=N/O)/[C@H]3OC\1)O)C[C@H]4C2 CKVMAPHTVCTEMM-ALPQRHTBSA-N 0.000 description 1
- 229940099245 milbemycin oxime Drugs 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- GLBLPMUBLHYFCW-UHFFFAOYSA-N n-(5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1NS(=O)(=O)C1=C(OC)N=CC=C1C(F)(F)F GLBLPMUBLHYFCW-UHFFFAOYSA-N 0.000 description 1
- JEFUQUGZXLEHLD-UHFFFAOYSA-N n-[(5-chloro-2-propan-2-ylphenyl)methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1=CC=C(Cl)C=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 JEFUQUGZXLEHLD-UHFFFAOYSA-N 0.000 description 1
- DHQKLWKZSFCKTA-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]pyridin-2-ylidene]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)N=C1C=CC=CN1CC1=CC=C(Cl)N=C1 DHQKLWKZSFCKTA-UHFFFAOYSA-N 0.000 description 1
- GBHVIWKSEHWFDD-UHFFFAOYSA-N n-[2-(4,6-dimethoxy-1,3,5-triazine-2-carbonyl)-6-fluorophenyl]-1,1-difluoro-n-methylmethanesulfonamide Chemical compound COC1=NC(OC)=NC(C(=O)C=2C(=C(F)C=CC=2)N(C)S(=O)(=O)C(F)F)=N1 GBHVIWKSEHWFDD-UHFFFAOYSA-N 0.000 description 1
- FITSYTCYOITKJL-UHFFFAOYSA-N n-[2-[(3,3-dimethyl-2-oxoazetidin-1-yl)methyl]phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound O=C1C(C)(C)CN1CC1=CC=CC=C1NS(=O)(=O)C(F)(F)F FITSYTCYOITKJL-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- HZDIJTXDRLNTIS-DAXSKMNVSA-N n-[[(z)-but-2-enoxy]methyl]-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(COC\C=C/C)C(=O)CCl HZDIJTXDRLNTIS-DAXSKMNVSA-N 0.000 description 1
- YNKFZRGTXAPYFD-UHFFFAOYSA-N n-[[2-chloro-3,5-bis(trifluoromethyl)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1Cl YNKFZRGTXAPYFD-UHFFFAOYSA-N 0.000 description 1
- DGPBHERUGBOSFZ-UHFFFAOYSA-N n-but-3-yn-2-yl-2-chloro-n-phenylacetamide Chemical compound C#CC(C)N(C(=O)CCl)C1=CC=CC=C1 DGPBHERUGBOSFZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical class CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 description 1
- NQPGZXOPMRKAGJ-UHFFFAOYSA-N n-ethyl-5-methyl-1-(3-methylbutan-2-yl)-n-pyridazin-4-ylpyrazole-4-carboxamide Chemical compound C=1C=NN=CC=1N(CC)C(=O)C=1C=NN(C(C)C(C)C)C=1C NQPGZXOPMRKAGJ-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical class [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- XHVDWCKBZSFUDE-UHFFFAOYSA-N n-phenylfuran-2-carboxamide Chemical class C=1C=COC=1C(=O)NC1=CC=CC=C1 XHVDWCKBZSFUDE-UHFFFAOYSA-N 0.000 description 1
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical group [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 description 1
- YTYGAJLZOJPJGH-UHFFFAOYSA-N noviflumuron Chemical compound FC1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F YTYGAJLZOJPJGH-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- LLLFASISUZUJEQ-UHFFFAOYSA-N orbencarb Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1Cl LLLFASISUZUJEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- UCDPMNSCCRBWIC-UHFFFAOYSA-N orthosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)N(C)C)=N1 UCDPMNSCCRBWIC-UHFFFAOYSA-N 0.000 description 1
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- WBTYBAGIHOISOQ-UHFFFAOYSA-N pent-4-en-1-yl 2-[(2-furylmethyl)(imidazol-1-ylcarbonyl)amino]butanoate Chemical compound C1=CN=CN1C(=O)N(C(CC)C(=O)OCCCC=C)CC1=CC=CO1 WBTYBAGIHOISOQ-UHFFFAOYSA-N 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 235000011197 perejil Nutrition 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- 229960003536 phenothrin Drugs 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
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000008298 phosphoramidates Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- URHWNXDZOULUHC-ULJHMMPZSA-N picarbutrazox Chemical compound CN1N=NN=C1\C(C=1C=CC=CC=1)=N/OCC1=CC=CC(NC(=O)OC(C)(C)C)=N1 URHWNXDZOULUHC-ULJHMMPZSA-N 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920005646 polycarboxylate Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WHMZYGMQWIBNOC-UHFFFAOYSA-N propan-2-yl n-(3,4-dimethoxyphenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)C)C=C1OC WHMZYGMQWIBNOC-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 231100000654 protein toxin Toxicity 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- DZVWKNFPXMUIFA-UHFFFAOYSA-N pyflubumide Chemical compound C1=C(CC(C)C)C(C(OC)(C(F)(F)F)C(F)(F)F)=CC=C1N(C(=O)C(C)C)C(=O)C1=C(C)N(C)N=C1C DZVWKNFPXMUIFA-UHFFFAOYSA-N 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 description 1
- DDIQWGKUSJOETH-UHFFFAOYSA-N pyrafluprole Chemical compound ClC=1C=C(C(F)(F)F)C=C(Cl)C=1N1N=C(C#N)C(SCF)=C1NCC1=CN=CC=N1 DDIQWGKUSJOETH-UHFFFAOYSA-N 0.000 description 1
- DWTVBEZBWMDXIY-UHFFFAOYSA-N pyrametostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=C(C)C(C=2C=CC=CC=2)=NN1C DWTVBEZBWMDXIY-UHFFFAOYSA-N 0.000 description 1
- URXNNPCNKVAQRA-XMHGGMMESA-N pyraoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC(C=2C=CC(Cl)=CC=2)=NN1C URXNNPCNKVAQRA-XMHGGMMESA-N 0.000 description 1
- DWSPRBSLSXQIEJ-UHFFFAOYSA-N pyrasulfotole Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1S(C)(=O)=O DWSPRBSLSXQIEJ-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940070846 pyrethrins Drugs 0.000 description 1
- CRFYLQMIDWBKRT-LPYMAVHISA-N pyribencarb Chemical compound C1=C(Cl)C(CNC(=O)OC)=CC(C(\C)=N\OCC=2N=C(C)C=CC=2)=C1 CRFYLQMIDWBKRT-LPYMAVHISA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
- MYKHANQTTIRZJK-UHFFFAOYSA-N pyridazine-3,4-dione Chemical class O=C1C=CN=NC1=O MYKHANQTTIRZJK-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- KWMWSMACCCIVRO-UHFFFAOYSA-N pyrimidin-2-yl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=NC=CC=N1 KWMWSMACCCIVRO-UHFFFAOYSA-N 0.000 description 1
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- YYXSCUSVVALMNW-FOWTUZBSSA-N pyriminostrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC(C(F)(F)F)=NC(NC=2C(=CC(Cl)=CC=2)Cl)=N1 YYXSCUSVVALMNW-FOWTUZBSSA-N 0.000 description 1
- BAUQXSYUDSNRHL-UHFFFAOYSA-N pyrimorph Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=1C=NC(Cl)=CC=1)=CC(=O)N1CCOCC1 BAUQXSYUDSNRHL-UHFFFAOYSA-N 0.000 description 1
- NMVCBWZLCXANER-UHFFFAOYSA-N pyriofenone Chemical compound COC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(C)C(Cl)=CN=C1OC NMVCBWZLCXANER-UHFFFAOYSA-N 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- DHTJFQWHCVTNRY-OEMAIJDKSA-N pyrisoxazole Chemical compound C1([C@@]2(C)CC(ON2C)C=2C=CC(Cl)=CC=2)=CC=CN=C1 DHTJFQWHCVTNRY-OEMAIJDKSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- JJSYXNQGLHBRRK-SFEDZAPPSA-N ryanodine Chemical compound O([C@@H]1[C@]([C@@]2([C@]3(O)[C@]45O[C@@]2(O)C[C@]([C@]4(CC[C@H](C)[C@H]5O)O)(C)[C@@]31O)C)(O)C(C)C)C(=O)C1=CC=CN1 JJSYXNQGLHBRRK-SFEDZAPPSA-N 0.000 description 1
- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 description 1
- 229960005393 sarolaner Drugs 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
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- JUNDBKFAZXZKRA-MAFYXNADSA-M sodium;2-[(e)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylate Chemical compound [Na+].N=1C=CC=C(C([O-])=O)C=1C(/C)=N/NC(=O)NC1=CC(F)=CC(F)=C1 JUNDBKFAZXZKRA-MAFYXNADSA-M 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- HEOYPZMAGQITRO-UHFFFAOYSA-N spirobudifen Chemical compound C(OCCCC)(OC1=C(C(OC12CCCCC2)=O)C2=C(C=C(C=C2)Cl)Cl)=O HEOYPZMAGQITRO-UHFFFAOYSA-N 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- WOPFPAIGRGHWAQ-UHFFFAOYSA-N spiropidion Chemical compound CCOC(=O)OC1=C(C=2C(=CC(Cl)=CC=2C)C)C(=O)N(C)C11CCN(OC)CC1 WOPFPAIGRGHWAQ-UHFFFAOYSA-N 0.000 description 1
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- CCEKAJIANROZEO-UHFFFAOYSA-N sulfluramid Chemical compound CCNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CCEKAJIANROZEO-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000005936 tau-Fluvalinate Chemical class 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical class N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- 229940111630 tea tree oil Drugs 0.000 description 1
- 239000010677 tea tree oil Substances 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- LWLJEQHTPVPKSJ-UHFFFAOYSA-N tebufloquin Chemical compound C1=C(C(C)(C)C)C=C2C(OC(=O)C)=C(C)C(C)=NC2=C1F LWLJEQHTPVPKSJ-UHFFFAOYSA-N 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- IHMQNZFRFVYNDS-UHFFFAOYSA-N tert-butyl n-amino-n-methylcarbamate Chemical compound CN(N)C(=O)OC(C)(C)C IHMQNZFRFVYNDS-UHFFFAOYSA-N 0.000 description 1
- QQDYOLJZDUADHV-CJNGLKHVSA-N tetflupyrolimet Chemical compound FC1=C(C=CC=C1)NC(=O)[C@H]1C(N(C[C@@H]1C1=CC(=CC=C1)C(F)(F)F)C)=O QQDYOLJZDUADHV-CJNGLKHVSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- KNDVJPKNBVIKML-UHFFFAOYSA-N tetraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(CN2N=C(N=N2)C(F)(F)F)=NN1C1=NC=CC=C1Cl KNDVJPKNBVIKML-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- DYLDNPYVDMQCFR-UHFFFAOYSA-N thiocyclam hydrochloride Chemical compound Cl.CN(C)C1CSSSC1 DYLDNPYVDMQCFR-UHFFFAOYSA-N 0.000 description 1
- ICTQUFQQEYSGGJ-UHFFFAOYSA-N thiocyclam oxalate Chemical compound OC(=O)C(O)=O.CN(C)C1CSSSC1 ICTQUFQQEYSGGJ-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- IHNSIFFSNUQGQN-UHFFFAOYSA-N tioxazafen Chemical compound C1=CSC(C=2ON=C(N=2)C=2C=CC=CC=2)=C1 IHNSIFFSNUQGQN-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- RSOBJVBYZCMJOS-CYBMUJFWSA-N tolprocarb Chemical compound FC(F)(F)COC(=O)N[C@@H](C(C)C)CNC(=O)C1=CC=C(C)C=C1 RSOBJVBYZCMJOS-CYBMUJFWSA-N 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical class CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- UZKQTCBAMSWPJD-UQCOIBPSSA-N trans-Zeatin Natural products OCC(/C)=C\CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-UQCOIBPSSA-N 0.000 description 1
- UZKQTCBAMSWPJD-FARCUNLSSA-N trans-zeatin Chemical compound OCC(/C)=C/CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-FARCUNLSSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- DBHVHTPMRCXCIY-UHFFFAOYSA-N tyclopyrazoflor Chemical compound N1=C(Cl)C(N(C(=O)CCSCCC(F)(F)F)CC)=CN1C1=CC=CN=C1 DBHVHTPMRCXCIY-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229940023877 zeatin Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by 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, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/04—Esters of silicic acids
Definitions
- the present invention relates to novel thiazolecarboxylic acid hydrazide compounds or salts thereof, and fungicidal compositions containing them as active ingredients.
- Patent Document 1 describes substitutions that further enhance resistance to abiotic stress (e.g., cold, heat, drought, salt, flood), promote plant growth, and/or contribute to increased plant yield.
- abiotic stress e.g., cold, heat, drought, salt, flood
- Heteroarylcarbonyl hydrazide compounds are described.
- compounds in which the substituted heteroaryl is thiazole compounds of general formulas (Ia19) to (Ia23) and general formula (Io20) in which the 2-position of thiazole is H, a pyridyl group, or a chloro group are described, and specific examples
- D1-1 to D1-681, D2-1 to D2-681, D3-1 to D3-681, D4-1 to D4-681, D5-1 to D5-681, and D6-1 to D6-681 is listed.
- Patent Document 1 does not describe the thiazolecarboxylic acid hydrazide compound of the following formula (I), that is, the 2-amino-4-halogeno-5-thiazolecarboxylic acid hydrazide compound with any specific examples. Further, Patent Document 1 does not include any specific description regarding the effect of the substituted heteroarylcarbonyl hydrazide compound on controlling plant diseases.
- Patent Document 2 describes a 2-halogeno-5-thiazolecarboxylic acid hydrazide compound as a plant disease control agent, but 2-amino-4-halogeno-5-thiazolecarboxylic acid represented by the following formula (I) Acid hydrazide compounds are not described.
- an object of the present invention is to provide a novel fungicidal composition that exhibits an excellent control effect on plant diseases regardless of the application situation.
- the present inventors found that a compound of the following formula (I) or a salt thereof having a 2-amino-4-halogeno-5-thiazolecarboxylic acid hydrazide structure is contained as an active ingredient. It has been found that the composition exhibits excellent control effects against harmful plant diseases.
- a thiazolecarboxylic acid hydrazide compound or a salt thereof having a specific chemical structure of the following formula (I) ⁇ Contains a compound that has a preventive control effect against plant diseases; ⁇ Contains a compound that has a therapeutic control effect against plant diseases; ⁇ Contains a compound that has both preventive and therapeutic effects on plant diseases; ⁇ There is little impact on the appearance of the plants to which it is applied, I found out. That is, the present invention is as follows. [1] Formula (I):
- R 1 is halogen
- R 2 is H or (C 1 -C 3 )-alkyl
- R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 3 )-alkyl substituted with at least one Z, or H
- R 2 and R 3 may be taken together to form a 3- to 5-membered ring with the nitrogen atom bonded to R 2 and R 3
- a method for controlling harmful plant diseases which includes the step of applying an effective amount of compound (I) to plants, plant pathogens, or soil.
- R 1 is a halogen
- R 2 is H or (C 1 -C 3 )-alkyl
- R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 3 )-alkyl substituted with at least one Z, or H
- R 2 and R 3 may be taken together to form a 3- to 5-membered ring with the nitrogen atom bonded to R 2 and R 3
- R 1A is a fluorine, chlorine, or bromine atom
- R 3A is methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl
- R 4A is halogen, (C 1 -C 2 )-alkyl, (C 1 )-haloalkyl, nitro, cyano, (C 1 )-alkylthio, or (C 1 )-haloalkylthio
- n is an integer from 1 to 5] or a salt thereof (hereinafter also referred to as compound (IA)).
- R 1B is a fluorine, chlorine, or bromine atom
- R 3B is methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl
- R 4B is halogen, (C 1 -C 2 )-alkyl, (C 1 )-haloalkyl, nitro, cyano, (C 1 )-alkylthio, or (C 1 )-haloalkylthio
- n is an integer from 1 to 5] or a salt thereof (hereinafter also referred to as compound (IB)).
- a bactericidal composition containing compound (IA) or compound (IB) as an active ingredient containing compound (IA) or compound (IB) as an active ingredient.
- a method for controlling harmful plant diseases which includes the step of applying an effective amount of compound (IA) or compound (IB) to plants, plant pathogens, or soil.
- the present composition exhibits superior control effects against plant diseases compared to compositions containing similar conventional compounds, and is useful as a fungicidal composition such as a fungicide for agricultural and horticultural use.
- compound (I), compound (IA), and compound (IB) will be explained. Note that compound (I) includes compound (IA) and compound (IB).
- the number of substituents R 4 , R 4A or R 4B on the phenyl group may be one, or two or more, In the case of two or more, R 4 , R 4A or R 4B may be the same or different.
- examples of halogen or halogen as a substituent include fluorine, chlorine, bromine, or iodine atoms.
- the number of halogens as a substituent may be one or more, and in the case of two or more, each halogen atom may be the same or different.
- the halogen as a substituent may be substituted at any position.
- C P -C T means that the number of carbon atoms is P to T.
- C 1 -C 3 means that the number of carbon atoms is 1 to 3.
- Examples of (C 1 -C 3 )-alkyl include straight-chain or branched alkyl groups having 1 to 3 carbon atoms, such as methyl, ethyl, normal propyl, or isopropyl.
- (C 1 -C 2 )-alkyl includes, for example, a straight-chain alkyl group having 1 to 2 carbon atoms such as methyl or ethyl.
- a (C 1 -C 4 )-alkyl moiety is a straight-chain or branched chain having 1 to 4 carbon atoms, such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tertiary-butyl. Examples include chain alkyl groups.
- (C 2 -C 5 )-Alkynyl is, for example, ethynyl, 1-propynyl, propargyl (also simply referred to as 2-propynyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1 , 3-butadiynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 3-pentyn-2-yl, 4-pentyn-3-yl, 4-pentyn-2 -yl, 2-methyl-3-butynyl, 1,3-pentadiynyl, 1,4-pentadiynyl or 2,4-pentadiynyl having at least one triple bond in any position, having 2 to 5 carbon atoms
- Examples include straight-chain or branched alkynyl groups
- (C 2 -C 4 )-Alkenyl is, for example, vinyl (also simply referred to as ethenyl), allyl (also simply referred to as 2-propenyl), 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1,3-butadien-2-yl, 1-methyl-1-propenyl, 2-buten-2-yl, 3-buten-2-yl, 2-methyl-2-propenyl or 3- Examples include straight-chain or branched alkenyl groups having 2 to 4 carbon atoms and having at least one double bond at any position, such as buten-3-yl.
- the alkenyl also includes allenyl groups having one integrated double bond, such as 1,2-propadienyl, 1,2-butadienyl, or 2,3-butadienyl.
- Examples of (C 2 -C 3 )-alkenyl include straight-chain or branched alkenyl groups having 2 to 3 carbon atoms, such as vinyl, allyl, 1-propenyl, isopropenyl, and the like.
- it may be only one of the E-form or the Z-form, or a mixture of the E-form and the Z-form in any ratio, and there are no particular limitations as long as the number of carbon atoms is within the specified range. It never happens.
- (C 3 -C 4 )-cycloalkyl includes, for example, a cycloalkyl group having 3 to 4 carbon atoms such as cyclopropyl or cyclobutyl.
- Examples of the (C 3 )-cycloalkyl moiety include a cycloalkyl group having 3 carbon atoms such as cyclopropyl.
- the (C 3 -C 6 )-cycloalkyloxy moiety includes, for example, a cycloalkyloxy group having 3 to 6 carbon atoms such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy. .
- (C 1 -C 3 )-Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 1-fluoroethyl, 2 -Fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, perfluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2 -dichloroethyl, 2,2,2-trichloroethyl, 1-chloro-1-fluoroethyl, 2-chloro-2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 1-fluoro-2-propyl
- (C 1 )-Haloalkyl is, for example, 1 to 3 identical or Mention may be made of alkyl groups having one carbon atom that are partially or completely substituted with different halogen atoms.
- (C 2 -C 4 )-Haloalkenyl is, for example, 2-fluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 2-chlorovinyl, 2,2-dichlorovinyl, 2-bromovinyl, 2,2- Dibromovinyl, 3-fluoroallyl, 3,3-difluoroallyl, 2,3,3-trifluoroallyl, 3,3-difluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 3- Chloroallyl, 3,3-dichloroallyl, 3,3-dichloro-1-propenyl, 3,3,3-trichloro-1-propenyl, 3,3-dichloro-3-fluor
- (C 2 -C 3 )-Haloalkenyl is, for example, 2-fluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 2-chlorovinyl, 2,2-dichlorovinyl, 2-bromovinyl, 2,2- Dibromovinyl, 3-fluoroallyl, 3,3-difluoroallyl, 2,3,3-trifluoroallyl, 3,3-difluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 3- Chloroallyl, 3,3-dichloroallyl, 3,3-dichloro-1-propenyl, 3,3,3-trichloro-1-propenyl, 3,3-dichloro-3-fluoro-1-propenyl, 3-chloro-3 , 3-difluoro-1-propenyl, 3-bromoallyl, 3,3-dibromoallyl, 2-fluoro-1-methylviny
- Examples include straight-chain or branched alkenyl groups having 2 to 3 carbon atoms substituted with the same or different halogen atoms.
- it may be only one of the E-form or the Z-form, or a mixture of the E-form and the Z-form in any ratio, and there are no particular limitations as long as the number of carbon atoms is within the specified range. It never happens.
- (C 1 -C 3 )-Alkyl substituted with at least one Z is, for example, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, dicyanomethyl, 2 , 2-dicyanoethyl, methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-Propoxyethyl, 2-isopropoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-iso Propoxypropyl, 3-methoxypropyl, 3-e
- (C 1 -C 3 )-alkoxy or (C 1 -C 3 )-alkoxy moiety is, for example, methoxy, ethoxy, normal propoxy or isopropoxy, straight or branched, having 1 to 3 carbon atoms.
- Examples include alkoxy groups.
- (C 1 -C 4 )-Alkoxy moieties are, for example, methoxy, ethoxy, normal propoxy, isopropoxy, normal butoxy, isobutoxy, secondary butoxy or tertiary butoxy, linear or branched, having 1 to 4 carbon atoms. Examples include chain alkoxy groups.
- the (C 1 -C 3 )-alkylthio or (C 1 -C 3 )-alkylthio moiety is, for example, a linear or branched chain having 1 to 3 carbon atoms, such as methylthio, ethylthio, n-propylthio, or isopropylthio. Examples include chain alkylthio groups.
- (C 1 )-Alkylthio includes, for example, a linear alkylthio group having one carbon atom, such as methylthio.
- (C 1 -C 3 )-Haloalkylthio is, for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloromethylthio, dichloromethylthio, trichloromethylthio, chlorodifluoromethylthio, dichlorofluoromethylthio, 2-fluoroethylthio, 2,2- Difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloroethylthio, 2,2-dichloroethylthio, 2,2,2-trichloroethylthio, perfluoroethylthio, perfluoropropylthio, perfluoroethylthio Fluoroisopropylthio, 3,3,3-trifluoropropylthio, 2,2,3,3,3-pentafluoropropylthio, 1,1,1,3,3,3-hexafluoroisopropy
- (C 1 )-Haloalkylthio means 1 to 3 identical or different halogen atoms, such as fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloromethylthio, dichloromethylthio, trichloromethylthio, chlorodifluoromethylthio, dichlorofluoromethylthio, etc. Examples include substituted linear alkylthio groups having one carbon atom.
- R 2 and R 3 together may form a 3- to 5-membered ring with the nitrogen atom bonded to R 2 and R 3 , which ring may be saturated or unsaturated.
- saturated rings include aziridine, azetidine or pyrrolidine
- unsaturated rings include pyrrole or dihydropyrrole.
- n is an integer from 1 to 5" means that n is 1, 2, 3, 4, or 5. Further, in specific embodiments of compound (I), compound (IA) or compound (IB), n is 1 to 2, 1 to 3, 1 to 4, 2 to 3, 2 to 4, 2 to 5, 3 to It may also be an integer from 4, 3 to 5, or 4 to 5.
- the salts of compound (I), compound (IA) or compound (IB) include all agriculturally acceptable salts, including alkali metal salts (e.g., sodium salts, potassium salts, etc.) , alkaline earth metal salts (e.g. magnesium salts, calcium salts, etc.), amine salts (dimethylamine salts, triethylamine salts, etc.), inorganic acid salts (e.g. hydrochlorides, perchlorates, sulfates, nitrates, etc.) or Examples include organic acid salts (eg, acetate, methanesulfonate, paratoluenesulfonate, oxalate, etc.).
- alkali metal salts e.g., sodium salts, potassium salts, etc.
- alkaline earth metal salts e.g. magnesium salts, calcium salts, etc.
- amine salts dimethylamine salts, triethylamine salts, etc.
- Compound (I), compound (IA) and compound (IB) exist in various isomers, such as optical isomers and geometric isomers, and the present invention includes both isomers and mixtures of isomers. Sometimes. Note that Compound (I), Compound (IA), and Compound (IB) also include various isomers other than those described above within the scope of common technical knowledge in the technical field. Furthermore, various isomers can be separately produced using common technical knowledge and general experimental methods in the relevant technical field.
- isomer may have a chemical structure different from the described structural formula, but a person skilled in the art will be able to fully recognize that they are in an isomer relationship, and therefore within the scope of the present invention. It is clear that there is.
- Compound (I) includes Compound (IA) and Compound (IB), and therefore, the following description also includes methods for producing Compound (IA) and Compound (IB).
- Compound (I) can be produced according to Production Method 1 (Reaction A to Reaction L) shown below and the usual salt production method, but the method for obtaining the compound is limited to these methods. isn't it.
- the compound (I) of the present invention can be subjected to various substituent conversion reactions well known in the art (e.g., alkylation reaction, haloalkylation reaction, cross-coupling reaction such as Suzuki coupling reaction) to the substituent on the phenyl group.
- reaction Sandmeyer type reaction, halogenation reaction, oxidation reaction, reduction reaction, etc.
- protection and deprotection reactions commonly used in this field may be applied in the production of the compounds of the present invention.
- the reaction may be carried out under an inert gas atmosphere such as nitrogen or argon, or a salt reagent may be used.
- Reaction A is a deprotection reaction, and is a method for obtaining the compound of formula (I) by removing the Boc group from the compound of formula (XX-a).
- the Boc group is a tert-butoxycarbonyl group.
- Reaction A is performed using known conditions used to remove the Boc group, such as Greene's PROTECTIVE GROUPS in ORGANIC SYNTHESIS (John Wiley and Sons, 2007, Peter G.M. .Wuts, Theodora W. Greene).
- This can be done by any method. More specifically, it can be carried out, for example, by reacting with an acid such as trifluoroacetic acid or hydrogen chloride in the presence of a solvent, or by reacting with trimethylsilyl triflate in the presence of a solvent and a base such as 2,6-lutidine. can.
- Reaction B is a method in which a compound of formula (II) and a compound of formula (III) are reacted to obtain a compound of formula (XX-b).
- Reaction C is a method in which a compound of formula (II-a) and a compound of formula (III) are reacted to obtain a compound of formula (XX-b).
- A is NH 2 or NH(Boc)
- R 2a is H, (C 1 -C 3 )-alkyl or Boc
- R 2a and R 3 may together form a 3- to 5-membered ring (eg aziridine, azetidine, pyrrolidine, dihydropyrrole or pyrrole) with the nitrogen atom attached to R 2a and R 3
- L is a leaving group, and examples thereof include halogen, alkoxy, aryloxy, alkylcarbonyloxy, and arylcarbonyloxy. Other symbols are as described above.
- Reaction B can usually be carried out in the presence of a dehydration condensation agent and a solvent, with the addition of a base if necessary.
- the compound of formula (III) can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per 1 equivalent of the compound of formula (II) (equivalents are molar equivalents, and the same applies below) ).
- a carbodiimide condensing agent such as N,N'-dicyclohexylcarbodiimide (DCC), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDC), or its hydrochloride; ; Imidazole condensing agent such as 1,1'-carbonyldiimidazole (CDI); 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride ( Triazine condensing agents such as DMT-MM); Phosphonium condensing agents such as 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP); 1-[bis(dimethylamino)methylene] -1H-1,2,3-triazolo[4,5-b]pyridinium uronium-based conden
- DCC N,N'-dicyclohe
- dehydration condensation agent can be used in an amount of 0.5 to 5 equivalents, preferably 1 to 2 equivalents, per equivalent of the compound of formula (II), and the additive can be used in an amount of 0.5 to 5 equivalents, preferably 1 to 2 equivalents, per equivalent of the compound of formula (II). 2 to 5 equivalents, preferably 1 to 2 equivalents can be used.
- the base in reaction B can be, for example, a carbonate such as sodium carbonate or potassium carbonate; a bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate; a metal hydroxide such as sodium hydroxide or potassium hydroxide; Metal hydrides such as sodium and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; sodium acetate and potassium acetate Alkali metal carboxylates such as; and the like, one type or two or more types can be appropriately selected and used in combination.
- a carbonate such as sodium carbonate or potassium carbonate
- a bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate
- a metal hydroxide such as sodium hydroxide or potassium hydroxide
- Metal hydrides such as sodium and potassium hydride
- amines such as triethylamine and N,N-d
- the base can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per 1 equivalent of the compound of formula (II).
- the solvent in reaction B may be any solvent as long as it is inert to the reaction; for example, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, Aliphatic hydrocarbons such as dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; dimethyl sulfoxide, sulfolane, N,N - Aprotic polar solvents such as dimethylacetamide, N,N-dimethylformamide, N-methyl
- the reaction temperature for reaction B is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.
- Reaction C can be carried out in the presence of a solvent and optionally with the addition of a base.
- the compound of formula (III) can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of formula (II-a).
- the base in reaction C can be, for example, a carbonate such as sodium carbonate or potassium carbonate; a bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate; a metal hydroxide such as sodium hydroxide or potassium hydroxide; Metal hydrides such as sodium and potassium hydride; Amines such as triethylamine and N,N-diisopropylethylamine; Pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; Sodium acetate and potassium acetate Alkali metal carboxylates such as; and the like, one type or two or more types can be appropriately selected and used in combination.
- a carbonate such as sodium carbonate or potassium carbonate
- a bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate
- a metal hydroxide such as sodium hydroxide or potassium hydroxide
- Metal hydrides such as sodium and potassium hydride
- Amines such as triethylamine and N,N-diis
- the base can be used in an amount of 0.1 to 10 equivalents, preferably 0.5 to 5 equivalents, per 1 equivalent of the compound of formula (II-a).
- the solvent in reaction C may be any solvent as long as it is inert to the reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, Aliphatic hydrocarbons such as dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; dimethyl sulfoxide, sulfolane, N,N - Aprotic polar solvents such as dimethylacetamide, N,N-dimethylformamide, N
- the reaction temperature for reaction C is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.
- the compound of formula (II) used in reaction B can be produced according to the following reaction 1-1, reaction 1-2 or a known method, or a commercially available product may be used.
- the compound of formula (III) can be produced according to Reaction 2-2, Reaction 2-4 or Reaction 2-6 below.
- the compound of formula (II-a) used in reaction C can be produced from the compound of formula (II) according to known methods, or a commercially available product may be used.
- Reaction D is a method of obtaining a compound of formula (I-a) via a compound of formula (XX-d) or formula (XX-e) by removing the Boc group from a compound of formula (XX-c). .
- Reaction D is to directly obtain a compound of formula (I-a) from a compound of formula (XX-c) without isolating the compound of formula (XX-d), formula (XX-e) or a mixture thereof. You can also do it.
- reaction D can be carried out according to reaction A above.
- Reaction E is a method in which a compound of formula (XX-f) is reacted with a compound of formula (IV-a) or a compound of formula (IV-b) to obtain a compound of formula (XX-g).
- Reaction F is a method of reducing a compound of formula (XX-g) to obtain a compound of formula (XX-h). Reactions E and F can also be carried out consecutively without isolating the compound of formula (XX-g).
- R 3a is H, (C 1 -C 2 )-alkyl, (C 2 -C 4 )-alkynyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, or (C 1 -C 2 )-alkyl substituted with Z, and R 3b is H or methyl.
- R 3a and R 3b may be taken together to form a 3-4 membered carbocycle (e.g. cyclopropyl or cyclobutyl), Y 1 is alkyl, Y 2 is H or alkyl, and other symbols is as described above.
- Reaction E can be carried out by adding an acid, a base, or a dehydrating agent as necessary, and a solvent may be used.
- the compound of formula (IV-a) or formula (IV-b) is usually used in an amount of 1 to 5 equivalents per equivalent of the compound of formula (XX-f), and may be used in excess if there is no problem with the reaction.
- the acid in reaction E may be either an inorganic acid or an organic acid, and examples of the inorganic acid include hydrochloric acid and sulfuric acid, and examples of the organic acid include acetic acid, methanesulfonic acid, and paratoluenesulfonic acid.
- the base in reaction E can be, for example, an alkali metal alkoxide such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; carbonate such as sodium carbonate, potassium carbonate; hydrogen carbonate such as sodium hydrogen carbonate, potassium hydrogen carbonate.
- Metal hydroxides such as sodium hydroxide and potassium hydroxide
- Metal hydrides such as sodium hydride and potassium hydride
- Amines such as triethylamine and N,N-diisopropylethylamine
- Pyridine 4-dimethyl
- Examples include pyridines such as aminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate; and the like.
- Examples of the dehydrating agent in reaction E include anhydrous magnesium sulfate, anhydrous sodium sulfate, and molecular sieves.
- the solvent in reaction E may be any solvent as long as it is inert to the reaction; for example, aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; aromatic hydrocarbons such as toluene and xylene; dioxane. , ethers such as tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as acetonitrile; protic polar solvents such as methanol and ethanol; water; etc.
- aliphatic halogenated hydrocarbons such as dichloromethane and chloroform
- aromatic hydrocarbons such as toluene and xylene
- dioxane. ethers such as tetrahydrofuran, diethyl ether and dimethoxyethane
- esters such as methyl acetate and ethyl acetate
- the reaction temperature for reaction E is usually about -20°C to 150°C, preferably about 0°C to 120°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours. .
- the compound of formula (IV-a) or formula (IV-b) used in reaction E can be produced according to a known method, or a commercially available product may be used.
- Reaction F can usually be carried out in the presence of a reducing agent and a solvent, with the addition of an acid if necessary. Further, reaction F can also be carried out by hydrogenation in a hydrogen atmosphere using palladium on carbon as a catalyst.
- Examples of the reducing agent in reaction F include sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, and 2-picoline-borane complex.
- the reducing agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of formula (XX-g).
- the acid may be either an inorganic acid or an organic acid, and examples of the inorganic acid include hydrochloric acid, and examples of the organic acid include acetic acid and trifluoroacetic acid.
- the acid can be used in an amount of 1 to 10 equivalents per equivalent of the compound of formula (XX-g).
- the solvent used when using a reducing agent may be any solvent as long as it is inert to the reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, chloride, etc.
- Aliphatic hydrocarbons such as methyl, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; methanol,
- protic polar solvents such as ethanol; water; and the like.
- the solvent used in the reaction using palladium on carbon as a catalyst in a hydrogen atmosphere may be any solvent as long as it is inert to the reaction, such as ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; acetic acid.
- ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane
- acetic acid One or more types can be appropriately selected from esters such as methyl and ethyl acetate; alcohols such as methanol, ethanol, and isopropanol; and water.
- esters such as methyl and ethyl acetate
- alcohols such as methanol, ethanol, and isopropanol
- water such as methanol, ethanol, and isopropanol
- it can also be carried out under pressurized conditions if necessary.
- the reaction temperature for reaction F is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.
- Reaction G is a deprotection reaction, and is a method for obtaining a compound of formula (XX-gb) by removing the Boc group of the compound of formula (XX-ga).
- reaction G can be carried out according to reaction A above.
- Reaction H is a method of reacting a compound of formula (II) with a compound of formula (V) to obtain a compound of formula (XX-g).
- Reaction I is a method in which a compound of formula (II-a) and a compound of formula (V) are reacted to obtain a compound of formula (XX-g).
- reaction H can be carried out according to reaction B above.
- the compound of formula (V) can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of formula (II).
- Reaction I can be carried out according to reaction C above.
- the compound of formula (V) can be used in an amount of 0.5 to 3 equivalents, preferably 0.7 to 1.5 equivalents, per 1 equivalent of the compound of formula (II-a).
- the compound of formula (V) used in Reaction H and Reaction I can be produced according to Reaction 2-5 below or a known method, or a commercially available product may be used.
- Reaction J is a method for obtaining a compound of formula (XX-j) by reacting a compound of formula (XX-i) with a compound of formula (VI).
- L 1 is a leaving group such as halogen, trifluoromethanesulfonyloxy, methanesulfonyloxy, paratoluenesulfonyloxy, etc.
- R 3c is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 3 -C 4 )-cycloalkyl, or (substituted with at least one Z) C 1 -C 3 )-alkyl, and the other symbols are as described above.
- Reaction J can usually be carried out in the presence of a base and a solvent, with the addition of a phase transfer catalyst if necessary.
- the compound of formula (VI) can be used in an amount of 1 to 5 equivalents, preferably 1 to 3 equivalents, per 1 equivalent of the compound of formula (XX-i).
- the base in reaction J can be, for example, an alkali metal alkoxide such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; carbonate such as sodium carbonate, potassium carbonate; hydrogen carbonate such as sodium hydrogen carbonate, potassium hydrogen carbonate.
- alkali metal alkoxide such as sodium methoxide, sodium ethoxide, potassium tert-butoxide
- carbonate such as sodium carbonate, potassium carbonate
- hydrogen carbonate such as sodium hydrogen carbonate, potassium hydrogen carbonate.
- Metal hydroxides such as sodium hydroxide and potassium hydroxide
- Metal hydrides such as sodium hydride and potassium hydride
- Amines such as triethylamine and N,N-diisopropylethylamine
- Pyridine 4-dimethyl
- pyridines such as aminopyridine and 2,6-lutidine
- organic lithium compounds such as n-butyllithium and lithium diisopropylamide
- alkali metal carboxylates such as sodium acetate and potassium acetate
- the base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, per 1 equivalent of the compound of formula (XX-i).
- the solvent in reaction J may be any solvent as long as it is inert to the reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, Aliphatic hydrocarbons such as dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; methanol, ethanol, propanol, tert- Alcohols such as butanol; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, ace
- phase transfer catalyst in reaction J examples include quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium chloride, and tetrabutylammonium hydrogen sulfate; crown ethers such as 18-crown-6-ether; etc. can be mentioned.
- the phase transfer catalyst can be used in an amount of 0.1 to 3 equivalents per equivalent of the compound of formula (XX-i).
- the reaction temperature for reaction J is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 10 minutes to 48 hours, preferably about 1 to 24 hours.
- the compound of formula (VI) used in reaction J can be produced according to a known method, or a commercially available product may be used.
- Reaction K is a method for obtaining a compound of formula (XX-b) by reacting a compound of formula (II-b) with a compound of formula (VII).
- Reaction K can be carried out according to the above reaction J.
- the compound of formula (VII) can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, per 1 equivalent of the compound of formula (II-b).
- the compound of formula (II-b) used in reaction K can be produced according to reaction 1-3 below or a known method, or a commercially available product may be used.
- the compound of formula (VII) used in reaction K can be produced according to a known method, or a commercially available product may be used.
- Reaction L is a method of hydrolyzing a compound of formula (XX-k) to obtain a compound of formula (XX-l).
- R 3d is (C 1 -C 3 )-alkyl substituted with at least one Z 1
- R Z1 is (C 3 -C 6 )- cycloalkyloxy, (C 1 -C 4 )-alkoxy, phenoxy or benzyloxy
- R 3e is (C 1 -C 3 )-alkyl substituted with at least one carboxy group.
- Other symbols are as described above.
- Reaction L can be carried out according to the general basic hydrolysis conditions of esters, for example, the method described in Tetrahedron, 2012, 68, 4682-4692.
- Reaction 1-1 is a method of oxidizing a compound of formula (1) to obtain a compound of formula (II).
- Reaction 1-2 is a method of hydrolyzing the compound of formula (2) to obtain the compound of formula (II).
- Reaction 1-3 is a method in which a compound of formula (II) or a compound of formula (II-a) is reacted with a compound of formula (3) to obtain a compound of formula (II-b).
- Reaction 1-1 can be carried out under general pinic oxidation conditions, for example, according to the method described in Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182.
- the compound of formula (1) used in reaction 1-1 can be prepared by a known method, for example, Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182, Journal of Organic Chemistry, 2005, 7 0,567-574, International Publication It can be produced according to the method described in No. 2020/028141 or Organic Process Research and Development, 2021, 25, 1167-1175, or a commercially available product may be used.
- Reaction 1-2 can be carried out under general ester hydrolysis conditions, for example, according to the method described in International Publication No. 2009/100171.
- the compound of formula (2) used in reaction 1-2 can be produced according to a known method, for example, the method described in International Publication No. 2012/006760, or it can be produced using a commercially available product. good.
- Reaction 1-3 can be carried out according to reaction B or reaction C above.
- the compound of formula (3) can be used in an amount of 0.5 to 10 equivalents, preferably 0.7 to 5 equivalents, per equivalent of the compound of formula (II) or the compound of formula (II-a).
- the compound of formula (3) used in reaction 1-3 can be prepared according to known methods, for example, European Journal of Organic Chemistry, 2003, 4757-4764, Synthetic Communications, 2017, 4 7, 1231-1238. It can be manufactured according to the method, or a commercially available product may be used.
- Reaction 2-1 is a method in which a compound of formula (10) is reacted with a compound of formula (3) to obtain a compound of formula (11).
- Reaction 2-2 is a method for reducing the compound of formula (11) to obtain the compound of formula (III). Reactions 2-1 and 2-2 can also be carried out consecutively without isolating the compound of formula (11).
- Reaction 2-3 is a method for obtaining a compound of formula (11-b) by reacting a compound of formula (11-a) with a compound of formula (VI).
- Reaction 2-4 is a method for obtaining a compound of formula (III) by reacting a compound of formula (VII) with a compound of formula (3).
- Reaction 2-5 is a method in which a compound of formula (III-a) is reacted with a compound of formula (IV-a) or a compound of formula (IV-b) to obtain a compound of formula (V).
- Reaction 2-6 is a method of reducing the compound of formula (V) to obtain the compound of formula (III-b). Reactions 2-5 and 2-6 can also be carried out consecutively without isolating the compound of formula (V).
- Reaction 2-1 can be carried out according to general hydrazonation conditions using an aldehyde and hydrazine, for example, the method described in Tetrahedron Letters, 2013, 54, 896-899.
- the compound of formula (3) can be used in an amount of 0.7 to 5 equivalents, preferably 1 to 2 equivalents, per 1 equivalent of the compound of formula (10).
- the compound of formula (10) used in reaction 2-1 can be produced according to a known method, or a commercially available product may be used.
- Reaction 2-2 can be carried out under general conditions for reducing hydrazone to hydrazine, for example, according to the method described in U.S. Patent Application Publication No. 2016/002251, Chemical Reviews, 2019, 119, 11857-11911. . It is also possible to reduce the 2-picoline/borane complex by adding an acid such as hydrochloric acid as necessary.
- Reaction 2-3 is performed under known hydrazone alkylation conditions, for example, Organic Letters, 2014, 16, 5940-5943, Chemistry-A European Journal, 2019, 25, 976-980, Journal of Or ganic Chemistry, 2006, 71, 7113-7116, etc.
- Reaction 2-4 is a known alkylation reaction of hydrazine, for example, the method described in US Patent Application Publication No. 2012/0157386, Organic Letters, 2014, 16, 4782-4785, International Publication No. 2018/221679, etc. This can be done in accordance with the above.
- Reaction 2-5 can be carried out according to reaction E, and reaction 2-6 can be carried out according to reaction F.
- Compound (I) which is the active ingredient of the present composition, is useful as an active ingredient of an agricultural and horticultural fungicide that can control plant diseases with a low dose.
- Compound (I) includes compound (IA) and compound (IB), and therefore, the following description also includes compound (IA) and compound (IB).
- Compound (I) controls plant diseases caused by plant pathogenic fungi belonging to, for example, Oomycetes, Phytomyxea, Ascomycetes, Basidiomycetes, Deuteromycetes, etc. can. Among them, it is particularly effective for controlling plant diseases derived from plant pathogenic fungi belonging to the Oomycetes and Phytomyxea.
- Oomycetes include Phytophthora infestans , Phytophthora palmivora, Phytophthora cactorum , Phytophthora capsici , and Phytophthora capsici .
- Oomycetes include Phytophthora infestans , Phytophthora palmivora, Phytophthora cactorum , Phytophthora capsici , and Phytophthora capsici .
- ( Phytophthora capsici ) eggplant or watermelon brown rot fungus ( Phytophthora capsici ), citrus brown rot fungus ( Phytophthora citricola ), adzuki bean stem blight fungus ( Phytophthora vignae f. sp. adzukicola ), edamame stem blight fungus ( Phytophthora megasperma var.
- Phytophthora such as onion or Phytophthora porri
- Pseudoperonospora such as cucumber, pumpkin, melon, zucchini downy mildew ( Pseudoperonospora cubensis ), hop downy mildew ( Pseudoperonospora humuli ) ( Pseudoperonospora ); Plasmopara (Pseudoperonospora) such as grape downy mildew ( Plasmopara viticol a), Mitsuba downy mildew ( Plasmopara nivea ); Hyaloperonospora ( Hyaloperonospora) such as cabbage or Chinese cabbage downy mildew Bacteria of the genus Bremia , such as lettuce downy mildew ( Bremia lactucae ); rice seedling damping-off fungus ( Pythium graminicola ), wheat brown snow rot
- Aphanomycetes such as Aphanomyces raphani and Aphanomyces cochlioides of radish root rot.
- Fungi of the genus Aphanomyces fungi of the genus Albugo, such as spinach, turnip, radish or napa white rust ( Albugo macrospora ), wasabi white rust ( Albugo wasabiae ) , and Japanese white rust ( Albugo ipomoeae-aquaticae ); Soybean or edamame downy mildew ( Peronospora manshurica ), broccoli or turnip downy mildew ( Peronospora parasitica ), green onion, spring onion or onion downy mildew ( Peronospora destructor ), spinach downy mildew ( Peronospora farinosa f. sp. Spinaciae ), basil Examples include bacteria of the genus Peronospora, such as downy milde
- Plasmodiophora bacteria such as Chinese cabbage, cabbage, cauliflower, napa, broccoli or turnip clubroot ( Plasmodiophora brassicae ); Polymyxa betae ( Beet necrotic yellow vein virus ) which transmits beet necrotic yellow vein virus.
- Bacteria of the genus Polymyxa such as Polymyxa betae ;
- Bacteria of the genus Spongospora such as Spongospora subterranea ;
- Examples include bacteria of the genus Olpidium, such as Olpidium virulentus, which transmits the lettuce bigvein virus.
- Erysiphe genus bacteria such as wheat powdery mildew ( Erysiphe graminis ); Setosphaeria genus bacteria such as corn soot spot fungus (Setosphaeria turcica); cucumber powdery mildew ( Sphaerotheca fuliginea ), Sphaerotheca such as strawberry powdery mildew ( Sphaerotheca humuli ); Uncinula such as grape powdery mildew ( Uncinula necator ); Podosphaera such as apple powdery mildew ( Podosphaera leucotricha ) ) genus; such as Mycosphaerella pinodes , Mycosphaerella pomi , Mycosphaerella musicola , Mycosphaerella nawae , and Mycosphaerella fragariae .
- Bacteria of the genus Mycosphaerella Bacteria of the genus Venturia , such as Venturia inaequalis and Venturia nashicola ; Pyrenophora teres , Pyrenophora graminea ); Sclerotinia sclerotiorum on beans, cucumbers, cabbage, Chinese cabbage, chili peppers, peppers or onions; Sclerotinia borealis on wheat; Sclerotinia borealis on tomatoes; Bacteria of the genus Sclerotinia such as Sclerotinia minor ) and Sclerotinia trifoliorum ; Bacteria of the genus Botryotinia such as Botryotinia arachidis; Cochliobolus Bacteria of the genus Cochliobolus such as Miyabeanus ; Bacteria of the genus Didymella such as Didymella bryoniae ; Bacteria of the
- basidiomycetes include Rhizoctonia genus bacteria such as rice sheath blight fungus ( Rhizoctonia solani ); Ustilago genus fungi such as wheat naked smut fungus ( Ustilago nuda ); oat crown rust fungus ( Puccinia coronata ); Bacteria of the genus Puccinia such as Puccinia recondita and Puccinia striiformis ; Bacteria of the genus Phakopsora such as Phakopsora pachyrhizi ; small grain fungi of wheat or barley snow rot Examples include Typhula genus bacteria such as Typhula incarnata or Typhula ishikariensis .
- Deuteromycetes include Septoria genus bacteria such as Septoria nodorum and Septoria tritici ; grapes, citrus, cucumbers, tomatoes, strawberries, eggplants, green beans, adzuki beans, peas, Botrytis cinerea on groundnuts , chili peppers, bell peppers, lettuce, onions, statice, carnations , roses, pansies or sunflowers, Botrytis allii on onions, Botrytis spp.
- Septoria genus bacteria such as Septoria nodorum and Septoria tritici ; grapes, citrus, cucumbers, tomatoes, strawberries, eggplants, green beans, adzuki beans, peas, Botrytis cinerea on groundnuts , chili peppers, bell peppers, lettuce, onions, statice, carnations , roses, pansies or sunflowers, Botrytis allii on onions, Botrytis spp.
- Bacteria of the genus Botrytis such as squamosa , Botrytis byssoidea or Botrytis tulipae ; Bacteria of the genus Fusarium such as Fusarium graminearum and Fusarium oxysporum ; Pyricularia Bacteria of the genus Pyricularia such as Pyricularia oryzae ; Bacteria of the genus Cercospora such as Cercospora beticola and Cercospora kakivora ; Colletotrichum orbiculare of cucumber, and Bacteria of the genus Coffea Colletotrichum fungi such as Colletotrichum coffeanum ; Alternaria alternata apple pathotype, Alternaria alternata Japanese pear pathotype, Potato summer blight or Tomato ring spot fungus ( Alternaria solani ), Cabbage or Alternaria fungi such as Chinese cabbage black spot fungus ( Alternaria
- Bacteria of the genus Gloeosporium such as Gloeosporium kaki ; Bacteria of the genus Fulvia such as Fulvia fulva ; Corynespora of cucumber Examples include Corynespora genus bacteria such as cassiicola ). Also included are fungi of the genus Physoderma, such as corn spot disease fungus (Physoderma maydis).
- the present composition can preventatively or therapeutically control various diseases.
- this composition is effective against various diseases that are problematic in the field of agriculture and horticulture, such as seedling damping-off caused by Pythium, blast caused by Pyricularia, baka-nae caused by Fusarium, sesame leaf blight caused by Cochliobolus, and rhizoctonia.
- Rice diseases such as sheath blight; powdery mildew caused by Erysiphe bacteria, Fusarium head or crown rot caused by Fusarium fungi, rust caused by Puccinia fungi, brown snow rot caused by Pythium fungi, bare smut caused by Ustilago fungi, and pseudocirco Wheat diseases such as eye spot disease caused by Spora fungi, leaf blight or rot blight caused by Septoria fungi; Fusarium head blight caused by Fusarium fungi, leaf spot disease caused by Physoderma fungi, rust caused by Puccinia fungi, soot spot disease caused by Setosphaeria fungi, Diseases of corn such as sesame leaf blight caused by Cochliobolus fungi, root rot caused by Pythium fungi, and smut caused by Ustilago fungi; smut caused by Ustilago fungi, leaf scorch caused by
- grass crops such as sugarcane diseases such as soot disease caused by Caldaromyces fungi and leaf blight caused by Pseudocercospora; powdery mildew caused by Oedium fungi, rust caused by Phacopsora fungi, and downy mildew caused by Peronospora fungi.
- leguminous crops such as late blight or stem blight caused by Phytophthora fungi, anthracnose caused by Colletotrichum, sclerotia caused by Sclerotinia fungi, gray mold caused by Botrytis fungi, and root rot or damping-off caused by Fusarium fungi; yellowing disease caused by Fusarium fungi, downy mildew caused by Peronospora fungi or Hyaloperonospora fungi, black spot disease caused by Alternaria fungi, root rot disease caused by Forma fungi, clubroot disease caused by Plasmodiophora fungi, root necking disease caused by Aphanomyces fungi, Diseases of cruciferous crops such as Pythium rot caused by Pythium; downy mildew caused by Bremia, late blight caused by Phytophthora, gray mold caused by Botrytis, sclerotium caused by Sclerotinia,
- Crop diseases anthracnose caused by Colletotrichum, powdery mildew caused by Sphaeroteca, vine blight caused by Didymera, downy mildew caused by Pseudoperonospora, late blight or brown rot caused by Phytophthora, brown spot caused by Corynespora.
- Diseases of Cucurbitaceae crops such as vine split disease caused by Fusarium; downy mildew caused by Peronospora, late blight caused by Phytophthora, gray mold caused by Botrytis, sclerotia caused by Sclerotinia, and rust caused by Puccinia.
- strawberries such as dry rot caused by Monilinia bacteria, powdery mildew caused by Podosphaera bacteria, leaf spot disease caused by Alternaria bacteria, scab caused by Venturia bacteria, anthracnose caused by Glomerella bacteria, and brown spot caused by Diplocarpon bacteria.
- Diseases of apples such as ring spot caused by Botryosphaeria, sooty spot caused by Digophiara, sooty spot caused by Gloeodes, and black spot caused by Mycosphaerella; scab caused by Venturia and black spot caused by Alternaria.
- Rosaceae crops such as peach diseases
- Diseases of Rutaceae crops such as black spot caused by Diaporte fungi, scab caused by Yersinoe fungi, and citrus diseases such as Fusarium damping off caused by Fusarium fungi
- Gloeosporium Diseases of persimmonaceous crops such as fungal anthracnose, leaf drop caused by Circospora, powdery mildew caused by Factinia, and sooty spot caused by Digophiala
- anthracnose caused by Colletotrichum and ring spot caused by Pestaloothiopsis are examples of Rosaceae crops.
- Camellia family crops such as red rot caused by Pseudomonas bacterium and blast disease caused by Exobasidium; diseases of Zingiberaceae crops such as rhizome rot caused by Pythium bacillus; It is effective in controlling plant diseases such as downy mildew caused by Peronospora and other diseases of Lamiaceae crops.
- Fusarium fungus or crown rot disease Colletotrichum fungus anthracnose, Tilletia fungus smut, Ustilago fungus streak disease, Cephalosporium bacterium streak disease, Septoria fungus blight, etc.
- Diseases of leguminous crops such as soybean diseases such as black spot, anthracnose caused by Colletotrichum, and downy mildew caused by Septogloeum; Diseases of cabbage such as bacterial spot, black rot caused by Xanthomonas fungi, root rot caused by Forma fungi; diseases of radish such as black spot caused by Alternaria fungus, yellow chlorosis caused by Fusarium fungus, black rot caused by Xanthomonas fungus; Diseases of cruciferous crops such as Chinese cabbage diseases such as black spot caused by Xanthomonas, black rot caused by Verticillium; ring spot caused by Alternaria, canker caused by Clavibacter, and canker caused by Xanthomonas.
- soybean diseases such as black spot, anthracnose caused by Colletotrichum, and downy mildew caused by Septogloeum
- Diseases of cabbage such as bacterial spot, black rot caused by Xanthomonas
- Diseases of tomatoes such as bacterial spot; Diseases of eggplant such as brown spot caused by Alternaria and brown spot caused by Homopsis; scab caused by Streptomyces, silver scab caused by Helmintosporium, and Spongospora. Diseases of solanaceous crops such as potato diseases such as powdery scab; diseases of cucurbitaceous crops such as black spot caused by Alternaria, bacterial spot caused by Pseudomonas, and bacterial brown spot caused by Xanthomonas.
- Seed-borne diseases such as downy mildew caused by Peronospora, wilt caused by Fusarium, and diseases of spinach such as anthracnose caused by Colletotrichum; It is also effective for Furthermore, it is also effective in controlling soil diseases caused by plant pathogenic bacteria such as Fusarium, Pythium, Rhizoctonia, Verticillium, Plasmodiophora, and Thielabiopsis.
- the present composition can be applied to plants, plant pathogens, or soil.
- the plant body refers to above-ground parts of a plant such as a tree trunk, stem, leaves, flowers, and fruits, and underground parts of a plant such as seeds, tubers, rhizomes, roots, seedlings, and transplanted seedlings.
- the soil refers to agricultural land such as fields, paddy fields, orchards, and non-agricultural land such as lawns and forests where plants are cultivated.
- the plants to which this composition is applied are not particularly limited as long as they are useful for agriculture and horticulture, but examples include grass crops (rice, wheat, barley, oats, rye, corn, sugarcane, etc.), leguminous crops ( soybean, kidney bean, adzuki bean, pea, groundnut, edamame, alfalfa, etc.), cruciferous crops (cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, napa, rapeseed, wasabi, etc.), Asteraceae crops (lettuce, burdock, Japanese chrysanthemum) , sunflowers, etc.), Solanaceae crops (potatoes, eggplants, tomatoes, green peppers, tobacco, chili peppers, etc.), Cucurbitaceae crops (cucumbers, pumpkins, melons, watermelons, chili peppers, zucchini, etc.), Amaryllidaceae crops (alliums, chives, etc.) ,
- the plants include plants grown using genetic recombination technology or gene editing technology, such as plants that have been endowed with environmental stress tolerance, herbicide tolerance, pest tolerance, disease tolerance, etc., or plants that have been endowed with growth, fertility traits, etc. Includes plants whose quality and yield have been modified.
- the present composition is usually prepared by mixing compound (I) and an adjuvant to form powders, granules, wettable powders, wettable powders, aqueous suspensions, oily suspensions, aqueous solutions, emulsions, solutions, etc. It can be formulated and used in various forms such as paste, aerosol, microspray, microcapsule, etc., but any formulation commonly used in the field may be used as long as it is compatible with the purpose of the present invention. Can be done.
- the auxiliary agents used in the formulation include solid carriers and liquid carriers, but surfactants and other formulation auxiliaries may also be added as necessary.
- the solid carrier include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch, and finely divided silica.
- the liquid carrier include water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N,N-dimethylformamide, dimethylacetamide, and N-methyl-2.
- Examples include pyrrolidone and alcohol.
- the surfactants include fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylate salts, alkyl sulfate ester salts, alkyl sulfates, alkylaryl sulfates, alkyl diglycol ether sulfates, Alcohol sulfate ester salt, alkyl sulfonate, alkylaryl sulfonate, aryl sulfonate, lignin sulfonate, alkyldiphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester salt, alkylaryl phosphate, styryl Aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether phosphate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene al
- formulation adjuvants include olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, and tung oil. , vegetable oil and mineral oil such as liquid paraffin; silicone; xanthan gum, and the like.
- auxiliary agents may be used alone or in combinations of two or more, as long as it does not depart from the purpose of the present invention.
- auxiliary agents those known in the field may be selected and used as appropriate, such as bulking agents, thickeners, anti-settling agents, anti-freezing agents, dispersion stabilizers, chemical damage reducers, etc.
- Various commonly used adjuvants such as antifungal agents and antifungal agents can also be used.
- the mixing ratio of compound (I) and various auxiliary agents is generally 0.001:99.999 to 95:5, preferably 0.005:99.995 to 90:10, by weight.
- they can be used as is, or diluted to a specified concentration with a diluent such as water, and various spreading agents (surfactants, vegetable oil, mineral oil, etc.) may be added as necessary. and can be used.
- the application of the present composition cannot be absolutely defined due to differences in weather conditions, formulation form, target crop, application time, application location, type and occurrence of plant diseases, etc.
- the present composition or a diluted product thereof can be applied by spraying, soil treatment, seed treatment, etc.
- compound (I) can be applied at an active ingredient concentration of 0.1 to 10,000 ppm, preferably 1 to 2000 ppm.
- the appropriate amount of the composition to be applied can be about 10 to 100,000 g per hectare.
- the appropriate amount of the composition to be applied can be about 0.01 to 1,000 g per hectare.
- the appropriate amount of the composition to be applied can be about 0.001 to 100 g, preferably about 0.01 to 1 g, per 1 kg of seeds.
- the above-mentioned spraying treatment is a treatment method for controlling plant pathogenic bacteria by spraying an effective amount of the present composition onto the surfaces of plant trunks, buds, stems, leaves, flowers, panicles, and fruits, or onto plant pathogenic bacteria.
- Examples include foliage spraying, tree trunk spraying, etc.
- the above-mentioned soil treatment is a method of treating soil with the present composition in order to infiltrate and transfer an effective amount of compound (I) from the roots of the plant into the interior of the plant in order to protect crops from damage caused by plant pathogens. be.
- irrigation treatment for example, irrigation treatment (drinking the present composition into the plant cultivation soil), soil mixing treatment (mixing the present composition with the plant cultivation soil), planting hole treatment, treatment at the base of the plant or between the plants (spraying or irrigation) ), mixing treatment with soil used for cultivation soil, seedling raising boxes, seedling raising trays, paper pots, seedling beds, etc.
- the seed treatment is a treatment method for controlling plant pathogens by applying the present composition directly or in the vicinity of seeds, bulbs, etc. of crops in order to protect crops from damage caused by plant pathogens. Examples include coating treatment, powder coating treatment, dipping treatment, and the like.
- seedling treatment irrigation or immersion
- immersion treatment immersion treatment of bulbs, tubers, scales, roots, etc.
- hydroponic treatment such as mixing with a hydroponic culture nutrient solution.
- the treatment may be on the whole plant or a part of the plant (foliage, buds, flowers, ears, fruits, trunks, seeds, bulbs, tubers, scales, roots, etc.).
- the present composition can be mixed or used in combination with other ingredients selected from other agricultural and horticultural chemicals, fertilizers, phytotoxicity reducers, etc. In this case, even more excellent effects and actions may be exhibited.
- the above-mentioned mixing or combination means using the present composition and other components simultaneously, separately, or at intervals of time.
- Other agricultural and horticultural chemicals include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, and plant growth regulators. Can be mentioned.
- mixed fungicidal compositions that are used in combination with this composition and one or more active ingredient compounds of other fungicides improve the application range, timing of chemical treatment, pesticidal activity, etc. in a favorable direction.
- the active ingredient compounds of this composition and other fungicides may be prepared separately and mixed together at the time of spraying, or both may be prepared and used together.
- the present invention also includes such mixed fungicides.
- the mixing ratio of Compound (I) and the active ingredient compounds of other fungicides is generally determined depending on differences in weather conditions, formulation form, target crop, application time, application location, type and occurrence of plant diseases, etc.
- the weight ratio can be generally 1:300 to 300:1, preferably 1:100 to 100:1.
- the total amount of active ingredient compounds per hectare can be 0.1 to 70,000 g, preferably 1 to 30,000 g.
- the present invention also includes a method for controlling plant diseases by applying such a mixed fungicidal composition.
- fungicidal composition containing compound (I) When applying the fungicidal composition containing compound (I), other agricultural and horticultural agents such as fungicides, insecticides, acaricides, nematicides, soil insecticides, antiviral agents, attractants, It is also possible to further treat with herbicides, plant growth regulators, etc.
- the active ingredient compound (common name) of the fungicide in the other agricultural and horticultural chemicals mentioned above can be appropriately selected, for example, from the following compound group. Even if there is no particular description, if salts, alkyl esters, various structural isomers such as optical isomers, etc. exist in these compounds, they are naturally included.
- Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil; Triazolopyrimidine compounds such as ametoctradin; Triazolobenzothiazole compounds such as tricyclazole; Pyridinamine compounds such as fluazinam; triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole , tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole oxpoconazole fumarate, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromco brom
- Organophosphorus compounds such as fosetyl-Al, tolclofos-Methyl, edifenphos, iprobenfos; Phthalimide compounds such as captan, captafol, folpet; Dicarboximide compounds such as procymidone, iprodione, vinclozolin; Benzanilide compounds such as flutolanil, mepronil, benodanil, flufenoxadiazam; Amides such as carpropamid, diclocymet, silthiofam, fenoxanil; benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, pidiflu Pyrazole carboxamides such as pydiflumetofen, sedaxane, isoflucypram, inpyrfluxam, pyrapropo
- Microbial fungicides such as Bacillus amyloliqefaciens strain QST713, Bacillus amyloliqefaciens strain FZB24, Bacillus amyloliqefaciens strain MBI600, Bacillus amyloliqefaciens strain D747, Pseudomonas fluorescens, Bacillus subtilis, Trichoderma atroviride SKT-1; and Tea tree oil. Like plant extract.
- the active ingredient compound (common name) of the insecticide, nematicide, acaricide, or soil insecticide among the other agricultural and horticultural chemicals mentioned above may be appropriately selected from the following compound groups, for example. can. Even if there is no particular description, if salts, alkyl esters, various structural isomers such as optical isomers, etc. exist in these compounds, they are naturally included.
- composition of the present invention may be applied in combination with the following compounds.
- microbial pesticides Antibiotics like abamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin oxime, lepimectin, spinosad, spinetoram and semi-synthetic antibiotics; Natural products such as azadirachtin, rotenone, ryanodine; repellents such as DEET; physical control agents such as paraffin oil, mineral oil; RNAi pesticides like ledprona.
- Antibiotics like abamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin oxime, lepimectin, spinosad, spinetoram and semi-synthetic antibiotics
- Natural products such as azadirachtin, rotenone, ryanodine
- repellents such as DEET
- physical control agents such as paraffin oil, mineral oil
- the active ingredient compounds are, for example, appropriately selected from the following compound groups. can do. Even if there is no particular description, if salts, alkyl esters, various structural isomers such as optical isomers, etc. exist in these compounds, they are naturally included.
- Desirable embodiments of the present invention are as follows. However, the present invention is not limited to these.
- a method for controlling harmful plant diseases which comprises applying an effective amount of a thiazolecarboxylic acid hydrazide compound represented by formula (I) or a salt thereof to plants, plant pathogens, or soil.
- a thiazolecarboxylic acid hydrazide compound represented by formula (I) or a salt thereof is containing a thiazolecarboxylic acid hydrazide compound represented by formula (I) or a salt thereof.
- R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, or at least 1
- the thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, which is (C 1 -C 3 )-alkyl substituted with Z.
- R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, or at least 1
- R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, or at least one (C 1 -C 3 )-alkylthio
- R 4 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, nitro, or cyano, according to any one of [3] to [30] above.
- R 4 is a chlorine atom, a fluorine atom, a bromine atom, methyl, trifluoromethyl, nitro, or cyano; That salt.
- n 3 and three R 4 are substituted at the 2-, 3-, and 4-positions of the phenyl group.
- Compound or its salt [52] n is 3, and three R4s are substituted at the 2nd, 4th, and 5th positions of the phenyl group, or three R4s are substituted at the 2nd, 3rd, and 4th positions of the phenyl group.
- n 3 and three R4s are substituted at the 2nd, 4th, and 5th positions of the phenyl group, or three R4s are substituted at the 2nd, 3rd, and 4th positions of the phenyl group.
- a thiazolecarboxylic acid hydrazide compound represented by formula (IA) or a salt thereof [54] A thiazolecarboxylic acid hydrazide compound represented by formula (IB) or a salt thereof. [55] A thiazolecarboxylic acid hydrazide compound represented by formula (IA) or formula (IB) or a salt thereof. [56] The thiazole carboxylic acid hydrazide compound or a salt thereof according to the above [53] or [55], wherein R 3A is methyl, ethyl, propargyl, allyl, or cyclopropyl.
- An agricultural and horticultural fungicide comprising the thiazolecarboxylic acid hydrazide compound or its salt according to any one of [4] to [62] above.
- a method for preventing harmful plant diseases comprising applying an effective amount of the thiazolecarboxylic acid hydrazide compound or its salt according to any one of [4] to [62] above to plants, plant pathogenic bacteria, or soil. How to control.
- the 1 H-NMR spectrum data of the compound of the present invention was measured in a measurement solvent using JEOL JNM-ECX (500 MHz) or Bruker AVANCE III HD (300 MHz) (1 H-nuclear magnetic resonance spectroscopy).
- the measurement solvent may contain tetramethylsilane (TMS) as an internal standard.
- TMS tetramethylsilane
- room temperature means approximately 10 to 30°C.
- a saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution under ice cooling to quench the reaction.
- the quenched reaction solution was made basic using 3N aqueous sodium hydroxide solution, and then the aqueous layer was extracted using ethyl acetate and heptane. Subsequently, the organic layer obtained by the extraction was washed successively with a 3N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure.
- Synthesis Example 2 Synthesis of 2-amino-4-chloro-N-(4-fluoro-2-methylbenzyl)-N'-methylthiazole-5-carbohydrazide (compound No. 105) (1) 4-fluoro- A solution of 2-methylbenzaldehyde (1.0 g) and 1-Boc-1-methylhydrazine (1.06 g) in ethanol (35 mL) was stirred at 75° C. for 3 hours. After cooling to room temperature, 2-picoline borane (1.82 g, 85%) and 3N aqueous hydrochloric acid solution (12 mL) were added and stirred overnight at room temperature to obtain a reaction mixture.
- Me is a methyl group
- Et is an ethyl group
- n-Pr is a normal propyl group
- i-Pr is an isopropyl group
- c-Pr is a cyclopropyl group
- i-Bu is an isobutyl group
- c-Bu is a cyclobutyl group
- c-Pentyl is a cyclopentyl group
- c-Hexyl is a cyclohexyl group
- CN is a cyano group
- NO 2 is a nitro group
- the type of the salt is shown in the physical properties column of Table 1.
- a compound described as HCl salt is a hydrochloride
- a compound described as TsOH salt is a para-toluenesulfonate
- a compound described as Na salt is a sodium salt.
- compound no. 254 is compound no. 1 hydrochloride
- compound no. 255 is compound no. 76 hydrochloride
- compound no. 256 is compound no. 78 hydrochloride.
- Compound no. 257 is compound no. para-toluene sulfonate of Compound No. 1
- Compound No. 258 is compound no. 76 para-toluene sulfonate
- compound no. 259 is compound no. 78 para-toluenesulfonate.
- Compound no. 524 is compound no. It is the sodium salt of 523.
- s is a singlet
- brs is a broad singlet
- d is a doublet
- t is a triplet
- q is a quartet.
- sext is a sextet
- sep is a septet
- m is a multiplet.
- Test Example 1 Bactericidal effect test against tomato late blight (Phytophthora infestans) (preventive effect test) Tomatoes were grown in vinyl pots with a diameter of 6 cm, and when they reached the 4.5 to 5.5 leaf stage, 10 ml of the chemical solution was sprayed with a spray gun. After the chemical solution dried (on the day of treatment), a spore suspension of Phytophthora infestans was spray inoculated and placed in an inoculation box at a temperature of 20° C. and a humidity of 95% or higher for 16 hours.
- each composition containing the following compounds showed a control rate of 90% or more against tomato late blight.
- compounds No. 35, 160, 178, and 179 showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 200 ppm, and the other compounds showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 400 ppm. This shows a control rate of 90% or more.
- Control rate (%) 100 - (X/Y) x 100
- X Lesion area rate of test compound (%)
- Y Lesion area rate of untreated area (%)
- Test Example 2 Bactericidal effect test against cucumber downy mildew ( Pseudoperonospora cubensis ) (preventive effect test) Cucumbers were grown in vinyl pots with a diameter of 6 cm, and when they reached the 1.2 to 1.5 leaf stage, 10 ml of the chemical solution was sprayed with a spray gun. After the chemical solution had dried (on the day of treatment), a spore suspension of cucumber downy mildew (Pseudoperonospora cubensis) was spray inoculated and placed in an inoculation box at a temperature of 20° C. and a humidity of 95% or more for 24 hours.
- each composition (active ingredient concentration: 400 ppm) containing the following compounds showed a control rate of 90% or more against cucumber downy mildew.
- Test Example 3 Bactericidal effect test against tomato late blight ( Phytophthora infestans ) (therapeutic effect test) Tomatoes were grown in plastic pots with a diameter of 6 cm, and when they reached the 4.5-5.5 leaf stage, they were spray-inoculated with a spore suspension of Phytophthora infestans and grown at a temperature of 20°C and a humidity of 95% or higher. It was placed in the inoculation box for 4 hours.
- 35, 160, 177, and 179 showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 200 ppm, and the other compounds showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 400 ppm. This shows a control rate of 90% or more.
- Comparative Test Compounds No. 78 and No. 193 were used as the active ingredients of the present composition, and Compound D6-15 shown below was used as the active ingredient of a composition containing the compound described in International Publication No. 2017/012965. , conducted a comparative test. Preparation of chemical solutions containing each compound: Using each test compound, each drug solution was prepared using the same preparation method as above. This chemical solution was used in Comparative Test Example 1 below. Comparative test example 1: Bactericidal effect test against tomato late blight (preventive effect test) 10 mL of the chemical solution was sprayed onto each tomato pot (cultivated in a vinyl pot with a diameter of 6 cm, 4.5 to 5.5 leaf stage) using a spray gun.
- Formulation example 1 (1) 20 parts by weight of the compound of formula (I), (2) 72 parts by weight of clay, and (3) 8 parts by weight or more of sodium ligninsulfonate are uniformly mixed to prepare a wettable powder.
- Formulation example 2 (1) 5 parts by weight of the compound of formula (I) (2) 95 parts by weight or more of talc are uniformly mixed to form a powder.
- Formulation example 3 (1) Compound of formula (I) 20 parts by weight (2) N,N'-dimethylacetamide 20 parts by weight (3) Polyoxyethylene alkylphenyl ether 10 parts by weight (4) Xylene 50 parts by weight or more uniformly Mix and dissolve to form an emulsion.
- Formulation example 4 (1) Clay 68 parts by weight (2) Sodium ligninsulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) Finely divided silica A mixture of 25 parts by weight or more of each component and the formula (I) compound at a weight ratio of 4:1 to form a wettable powder.
- Formulation example 5 (1) Compound of formula (I) 50 parts by weight (2) Polyoxyethylene alkylphenyl ether phosphate triethanolamine salt 2 parts by weight (3) Silicone 0.2 part by weight (4) Water 47.8 parts by weight or more Further, (5) 5 parts by weight of sodium polycarboxylate and (6) 42.8 parts by weight of anhydrous sodium sulfate are added to the undiluted solution after uniformly mixing and pulverizing the ingredients, and the mixture is uniformly mixed, granulated, and dried to form a granule wettable powder. .
- Formulation example 6 (1) Compound of formula (I) 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Phosphate of polyoxyethylene 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight ( 1) to (3) are mixed uniformly in advance, diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove the acetone to form granules.
- Formulation example 7 (1) Compound of formula (I) 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved. Ultra low volume formulation.
- Formulation example 8 (1) Compound of formula (I) 20 parts by weight (2) Polyoxyethylene alkylphenyl ether phosphate triethanolamine salt 2 parts by weight (3) Silicone 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5 ) Ethylene glycol 5 parts by weight (6) Water 72.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Provided is a disinfecting composition having an excellent controlling effect against plant disease. This disinfecting composition contains a thiazole carboxylic acid hydrazide compound represented by formula (I) (where each symbol is as defined in the Description), or a salt thereof, as the active ingredient and has an excellent controlling effect against plant disease.
Description
本発明は、新規チアゾールカルボン酸ヒドラジド化合物又はその塩、それらを有効成分として含有する殺菌組成物に関する。
The present invention relates to novel thiazolecarboxylic acid hydrazide compounds or salts thereof, and fungicidal compositions containing them as active ingredients.
特許文献1には、非生物的ストレス(例えば、寒冷、熱、干ばつ、塩、洪水)に対する耐性をさらに増強し、植物の生育を促進し、かつ/または植物産生量の増加に寄与する、置換ヘテロアリールカルボニルヒドラジド化合物が記載されている。置換ヘテロアリールがチアゾールである化合物としては、チアゾールの2位がH、ピリジル基又はクロロ基である一般式(Ia19)~一般式(Ia23)及び一般式(Io20)の化合物が記載され、具体例として化合物D1-1~D1-681、D2-1~D2-681、D3-1~D3-681、D4-1~D4-681、D5-1~D5-681、及びD6-1~D6-681が記載されている。
Patent Document 1 describes substitutions that further enhance resistance to abiotic stress (e.g., cold, heat, drought, salt, flood), promote plant growth, and/or contribute to increased plant yield. Heteroarylcarbonyl hydrazide compounds are described. As compounds in which the substituted heteroaryl is thiazole, compounds of general formulas (Ia19) to (Ia23) and general formula (Io20) in which the 2-position of thiazole is H, a pyridyl group, or a chloro group are described, and specific examples As compounds D1-1 to D1-681, D2-1 to D2-681, D3-1 to D3-681, D4-1 to D4-681, D5-1 to D5-681, and D6-1 to D6-681 is listed.
しかしながら、特許文献1には、下記式(I)のチアゾールカルボン酸ヒドラジド化合物、即ち、2-アミノ-4-ハロゲノ-5-チアゾールカルボン酸ヒドラジド化合物は具体例を伴って記載されていない。また特許文献1には、前記置換ヘテロアリールカルボニルヒドラジド化合物の植物病害に対する防除効果に関する具体的な記載も一切ない。
However, Patent Document 1 does not describe the thiazolecarboxylic acid hydrazide compound of the following formula (I), that is, the 2-amino-4-halogeno-5-thiazolecarboxylic acid hydrazide compound with any specific examples. Further, Patent Document 1 does not include any specific description regarding the effect of the substituted heteroarylcarbonyl hydrazide compound on controlling plant diseases.
特許文献2には、植物病害防除剤として2-ハロゲノ-5-チアゾールカルボン酸ヒドラジド化合物が記載されているが、下記式(I)で表される2-アミノ-4-ハロゲノ-5-チアゾールカルボン酸ヒドラジド化合物は記載されていない。
Patent Document 2 describes a 2-halogeno-5-thiazolecarboxylic acid hydrazide compound as a plant disease control agent, but 2-amino-4-halogeno-5-thiazolecarboxylic acid represented by the following formula (I) Acid hydrazide compounds are not described.
本発明者らは、特許文献1に記載される置換ヘテロアリールカルボニルヒドラジド化合物では、環境負荷は少ないものの植物病害に対して高薬量でも十分な防除効果を発揮できないことを見出した。また、既存の農園芸用殺菌剤において、施用場面によっては植物病害に対する実用上不十分な防除効果、薬剤耐性菌の出現及び環境負荷(周辺の植物や生態系への影響)などの問題が懸念される。したがって、本発明の目的は、施用場面にかかわらず、植物病害に対する優れた防除効果を発揮する新規な殺菌組成物を提供することである。
The present inventors have discovered that the substituted heteroarylcarbonyl hydrazide compound described in Patent Document 1 does not have a sufficient control effect against plant diseases even at high doses, although it has a small environmental burden. In addition, there are concerns that existing agricultural and horticultural fungicides may have insufficient effectiveness in controlling plant diseases depending on the application situation, the emergence of drug-resistant bacteria, and environmental burden (impact on surrounding plants and ecosystems). be done. Therefore, an object of the present invention is to provide a novel fungicidal composition that exhibits an excellent control effect on plant diseases regardless of the application situation.
本発明者らは上記の課題を解決すべく鋭意検討した結果、2-アミノ-4-ハロゲノ-5-チアゾールカルボン酸ヒドラジド構造を有する下記式(I)の化合物又はその塩を有効成分として含有する組成物が有害な植物病害に対して優れた防除効果を発現することを見出した。
As a result of intensive studies to solve the above problems, the present inventors found that a compound of the following formula (I) or a salt thereof having a 2-amino-4-halogeno-5-thiazolecarboxylic acid hydrazide structure is contained as an active ingredient. It has been found that the composition exhibits excellent control effects against harmful plant diseases.
また、本発明者らは、下記式(I)の特定の化学構造を有するチアゾールカルボン酸ヒドラジド化合物又はその塩に、
・植物病害に対する予防的防除効果を有する化合物が含まれること、
・植物病害に対する治療的防除効果を有する化合物が含まれること、
・植物病害に対する予防的防除効果と治療的防除効果を兼ね備えた化合物が含まれること、
・施用された植物の生育に係る外観的な影響が少ないこと、
を見出した。
すなわち本発明は以下の通りである。
[1]式(I): The present inventors also found that a thiazolecarboxylic acid hydrazide compound or a salt thereof having a specific chemical structure of the following formula (I),
・Contains a compound that has a preventive control effect against plant diseases;
・Contains a compound that has a therapeutic control effect against plant diseases;
・Contains a compound that has both preventive and therapeutic effects on plant diseases;
・There is little impact on the appearance of the plants to which it is applied,
I found out.
That is, the present invention is as follows.
[1] Formula (I):
・植物病害に対する予防的防除効果を有する化合物が含まれること、
・植物病害に対する治療的防除効果を有する化合物が含まれること、
・植物病害に対する予防的防除効果と治療的防除効果を兼ね備えた化合物が含まれること、
・施用された植物の生育に係る外観的な影響が少ないこと、
を見出した。
すなわち本発明は以下の通りである。
[1]式(I): The present inventors also found that a thiazolecarboxylic acid hydrazide compound or a salt thereof having a specific chemical structure of the following formula (I),
・Contains a compound that has a preventive control effect against plant diseases;
・Contains a compound that has a therapeutic control effect against plant diseases;
・Contains a compound that has both preventive and therapeutic effects on plant diseases;
・There is little impact on the appearance of the plants to which it is applied,
I found out.
That is, the present invention is as follows.
[1] Formula (I):
R2はH又は(C1-C3)-アルキルであり、
R3は(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、(C3-C4)-シクロアルキル、(C2-C4)-ハロアルケニル、少なくとも1個のZで置換された(C1-C3)-アルキル、又はHであり、
R2とR3が一緒になって、R2とR3に結合した窒素原子と3~5員環を形成してもよく、
Zはシアノ、ハロゲン、(C1-C3)-アルコキシ、(C3)-シクロアルキル、(C1-C3)-アルキルチオ、-C(=O)RZ、ヒドロキシ、又はトリ(C1-C4)-アルキルシリルオキシであり、
RZは(C1-C4)-アルキル、(C3-C6)-シクロアルキルオキシ、(C1-C4)-アルコキシ、フェノキシ、ベンジルオキシ、又はヒドロキシであり、
R4はハロゲン、(C1-C3)-アルキル、(C1-C3)-ハロアルキル、ニトロ、シアノ、(C1-C3)-アルキルチオ、(C1-C3)-ハロアルキルチオ、(C2-C3)-アルケニル、(C2-C3)-ハロアルケニル、又は(C1-C3)-アルコキシであり、
nは1から5の整数である]で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩(以下、化合物(I)ともいう)を有効成分として含有する殺菌組成物(以下、本組成物ともいう)。
R 2 is H or (C 1 -C 3 )-alkyl;
R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 3 )-alkyl substituted with at least one Z, or H;
R 2 and R 3 may be taken together to form a 3- to 5-membered ring with the nitrogen atom bonded to R 2 and R 3 ,
Z is cyano, halogen, (C 1 -C 3 )-alkoxy, (C 3 )-cycloalkyl, (C 1 -C 3 )-alkylthio, -C(=O)R Z , hydroxy, or tri(C 1 -C 4 )-alkylsilyloxy,
R Z is (C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyloxy, (C 1 -C 4 )-alkoxy, phenoxy, benzyloxy, or hydroxy;
R 4 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, nitro, cyano, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-haloalkylthio, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, or (C 1 -C 3 )-alkoxy,
A bactericidal composition (hereinafter also referred to as the present composition) containing a thiazolecarboxylic acid hydrazide compound or its salt (hereinafter also referred to as compound (I)) as an active ingredient, where n is an integer from 1 to 5. .
[2]化合物(I)の有効量を、植物体、植物病原菌又は土壌に施用する工程を含む有害な植物病害を防除する方法。
[2] A method for controlling harmful plant diseases, which includes the step of applying an effective amount of compound (I) to plants, plant pathogens, or soil.
[3]式(I):
[3] Formula (I):
R2はH又は(C1-C3)-アルキルであり、
R3は(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、(C3-C4)-シクロアルキル、(C2-C4)-ハロアルケニル、少なくとも1個のZで置換された(C1-C3)-アルキル、又はHであり、
R2とR3が一緒になって、R2とR3に結合した窒素原子と3~5員環を形成してもよく、
Zはシアノ、ハロゲン、(C1-C3)-アルコキシ、(C3)-シクロアルキル、(C1-C3)-アルキルチオ、-C(=O)RZ、ヒドロキシ、又はトリ(C1-C4)-アルキルシリルオキシであり、
RZは(C1-C4)-アルキル、(C3-C6)-シクロアルキルオキシ、(C1-C4)-アルコキシ、フェノキシ、ベンジルオキシ、又はヒドロキシであり、
R4はハロゲン、(C1-C3)-アルキル、(C1-C3)-ハロアルキル、ニトロ、シアノ、(C1-C3)-アルキルチオ、(C1-C3)-ハロアルキルチオ、(C2-C3)-アルケニル、(C2-C3)-ハロアルケニル、又は(C1-C3)-アルコキシであり、
nは1から5の整数である]で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩。
R 2 is H or (C 1 -C 3 )-alkyl;
R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 3 )-alkyl substituted with at least one Z, or H;
R 2 and R 3 may be taken together to form a 3- to 5-membered ring with the nitrogen atom bonded to R 2 and R 3 ,
Z is cyano, halogen, (C 1 -C 3 )-alkoxy, (C 3 )-cycloalkyl, (C 1 -C 3 )-alkylthio, -C(=O)R Z , hydroxy, or tri(C 1 -C 4 )-alkylsilyloxy,
R Z is (C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyloxy, (C 1 -C 4 )-alkoxy, phenoxy, benzyloxy, or hydroxy;
R 4 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, nitro, cyano, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-haloalkylthio, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, or (C 1 -C 3 )-alkoxy,
n is an integer from 1 to 5] A thiazolecarboxylic acid hydrazide compound or a salt thereof.
[4]式(IA):
[4] Formula (IA):
R3Aはメチル、エチル、ノルマルプロピル、プロパルギル、アリル、又はシクロプロピルであり、
R4Aはハロゲン、(C1-C2)-アルキル、(C1)-ハロアルキル、ニトロ、シアノ、(C1)-アルキルチオ、又は(C1)-ハロアルキルチオであり、
nは1から5の整数である]で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩(以下、化合物(IA)ともいう)。
R 3A is methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl;
R 4A is halogen, (C 1 -C 2 )-alkyl, (C 1 )-haloalkyl, nitro, cyano, (C 1 )-alkylthio, or (C 1 )-haloalkylthio;
n is an integer from 1 to 5] or a salt thereof (hereinafter also referred to as compound (IA)).
[5]式(IB):
[5] Formula (IB):
R3Bはメチル、エチル、ノルマルプロピル、プロパルギル、アリル、又はシクロプロピルであり、
R4Bはハロゲン、(C1-C2)-アルキル、(C1)-ハロアルキル、ニトロ、シアノ、(C1)-アルキルチオ、又は(C1)-ハロアルキルチオであり、
nは1から5の整数である]で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩(以下、化合物(IB)ともいう)。
R 3B is methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl;
R 4B is halogen, (C 1 -C 2 )-alkyl, (C 1 )-haloalkyl, nitro, cyano, (C 1 )-alkylthio, or (C 1 )-haloalkylthio;
n is an integer from 1 to 5] or a salt thereof (hereinafter also referred to as compound (IB)).
[6]化合物(IA)又は化合物(IB)を有効成分として含有する殺菌組成物。
[6] A bactericidal composition containing compound (IA) or compound (IB) as an active ingredient.
[7]化合物(IA)又は化合物(IB)の有効量を、植物体、植物病原菌又は土壌に施用する工程を含む有害な植物病害を防除する方法。
[7] A method for controlling harmful plant diseases, which includes the step of applying an effective amount of compound (IA) or compound (IB) to plants, plant pathogens, or soil.
本組成物は、類似する従来化合物を含む組成物に比して、植物病害に対して優れた防除効果を発揮し、農園芸用殺菌剤のような殺菌組成物として有用である。
The present composition exhibits superior control effects against plant diseases compared to compositions containing similar conventional compounds, and is useful as a fungicidal composition such as a fungicide for agricultural and horticultural use.
化合物(I)、化合物(IA)及び化合物(IB)の置換基及び化学構造の形態について説明する。なお、化合物(I)には化合物(IA)及び化合物(IB)を包含する。
The substituent groups and chemical structure forms of compound (I), compound (IA), and compound (IB) will be explained. Note that compound (I) includes compound (IA) and compound (IB).
化合物(I)、化合物(IA)及び化合物(IB)において、フェニル基上の置換基であるR4、R4A又はR4Bの置換数は1個でもよく、2個以上であってもよく、2個以上の場合、R4、R4A又はR4Bは各々同一でも相異なってもよい。
化合物(I)、化合物(IA)及び化合物(IB)において、ハロゲン又は置換基としてのハロゲンは、フッ素、塩素、臭素、又はヨウ素の各原子が挙げられる。置換基としてのハロゲンの数は1個又は2個以上であってもよく、2個以上の場合、各ハロゲン原子は各々同一でも相異なってもよい。また、置換基としてのハロゲンの置換位置は何れの位置でもよい。 In compound (I), compound (IA) and compound (IB), the number of substituents R 4 , R 4A or R 4B on the phenyl group may be one, or two or more, In the case of two or more, R 4 , R 4A or R 4B may be the same or different.
In compound (I), compound (IA) and compound (IB), examples of halogen or halogen as a substituent include fluorine, chlorine, bromine, or iodine atoms. The number of halogens as a substituent may be one or more, and in the case of two or more, each halogen atom may be the same or different. Furthermore, the halogen as a substituent may be substituted at any position.
化合物(I)、化合物(IA)及び化合物(IB)において、ハロゲン又は置換基としてのハロゲンは、フッ素、塩素、臭素、又はヨウ素の各原子が挙げられる。置換基としてのハロゲンの数は1個又は2個以上であってもよく、2個以上の場合、各ハロゲン原子は各々同一でも相異なってもよい。また、置換基としてのハロゲンの置換位置は何れの位置でもよい。 In compound (I), compound (IA) and compound (IB), the number of substituents R 4 , R 4A or R 4B on the phenyl group may be one, or two or more, In the case of two or more, R 4 , R 4A or R 4B may be the same or different.
In compound (I), compound (IA) and compound (IB), examples of halogen or halogen as a substituent include fluorine, chlorine, bromine, or iodine atoms. The number of halogens as a substituent may be one or more, and in the case of two or more, each halogen atom may be the same or different. Furthermore, the halogen as a substituent may be substituted at any position.
化合物(I)、化合物(IA)及び化合物(IB)において、「CP-CT」との表記は、炭素原子数がP乃至Tであることを意味する。例えば「C1-C3」との表記は、炭素原子数が1乃至3であることを意味する。
In compound (I), compound (IA) and compound (IB), the expression "C P -C T " means that the number of carbon atoms is P to T. For example, the notation "C 1 -C 3 " means that the number of carbon atoms is 1 to 3.
(C1-C3)-アルキルは、例えば、メチル、エチル、ノルマルプロピル、又はイソプロピルのような炭素原子数1~3個の直鎖又は分岐鎖状のアルキル基が挙げられる。(C1-C2)-アルキルは、例えば、メチル又はエチルのような炭素原子数1~2個の直鎖状のアルキル基が挙げられる。(C1-C4)-アルキル部分は、例えば、メチル、エチル、ノルマルプロピル、イソプロピル、ノルマルブチル、イソブチル、セカンダリ-ブチル又はターシャリーブチルのような炭素原子数1~4個の直鎖又は分岐鎖状のアルキル基が挙げられる。
(C2-C5)-アルキニルは、例えば、エチニル、1-プロピニル、プロパルギル(単に2-プロピニルともいう)、1-ブチニル、2-ブチニル、3-ブチニル、1-メチル-2-プロピニル、1,3-ブタジイニル、1-ペンチニル、2-ペンチニル、3-ペンチニル、4-ペンチニル、3-メチル-1-ブチニル、3-ペンチン-2-イル、4-ペンチン-3-イル、4-ペンチン-2-イル、2-メチル-3-ブチニル、1,3-ペンタジイニル、1,4-ペンタジイニル又は2,4-ペンタジイニル等の任意の位置に少なくとも1つの三重結合を有する、炭素原子数2~5個の直鎖又は分岐鎖状のアルキニル基が挙げられる。
(C2-C4)-アルケニルは、例えば、ビニル(単にエテニルともいう)、アリル(単に2-プロペニルともいう)、1-プロペニル、イソプロペニル、1-ブテニル、2-ブテニル、3-ブテニル、1,3-ブタジエニル、1,3-ブタジエン-2-イル、1-メチル-1-プロペニル、2-ブテン-2-イル、3-ブテン-2-イル、2-メチル-2-プロペニル又は3-ブテン-3-イル等の任意の位置に少なくとも1つの二重結合を有する、炭素原子数2~4個の直鎖又は分岐鎖状のアルケニル基が挙げられる。さらに、前記アルケニルには、1つの集積二重結合を有するアレニル基も含み、例えば、1,2-プロパジエニル、1,2-ブタジエニル、又は2,3-ブタジエニルが挙げられる。(C2-C3)-アルケニルは、例えば、ビニル、アリル、1-プロペニル又はイソプロペニル等のような直鎖又は分岐鎖状の炭素原子数2~3個のアルケニル基が挙げられる。また、幾何異性体がある場合、E体又はZ体のどちらか一方のみ、或いはE体とZ体との任意の割合の混合物であり、指定される炭素数の範囲であれば、特に限定されることはない。
(C3-C4)-シクロアルキルは、例えば、シクロプロピル又はシクロブチルのような炭素原子数3~4個のシクロアルキル基が挙げられる。(C3)-シクロアルキル部分は、例えば、シクロプロピルのような炭素原子数3個のシクロアルキル基が挙げられる。
また、(C3-C6)-シクロアルキルオキシ部分は、例えば、シクロプロピルオキシ、シクロブチルオキシ、シクロペンチルオキシ又はシクロへキシルオキシのような炭素原子数3~6個のシクロアルキルオキシ基が挙げられる。 Examples of (C 1 -C 3 )-alkyl include straight-chain or branched alkyl groups having 1 to 3 carbon atoms, such as methyl, ethyl, normal propyl, or isopropyl. (C 1 -C 2 )-alkyl includes, for example, a straight-chain alkyl group having 1 to 2 carbon atoms such as methyl or ethyl. A (C 1 -C 4 )-alkyl moiety is a straight-chain or branched chain having 1 to 4 carbon atoms, such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tertiary-butyl. Examples include chain alkyl groups.
(C 2 -C 5 )-Alkynyl is, for example, ethynyl, 1-propynyl, propargyl (also simply referred to as 2-propynyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1 , 3-butadiynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 3-pentyn-2-yl, 4-pentyn-3-yl, 4-pentyn-2 -yl, 2-methyl-3-butynyl, 1,3-pentadiynyl, 1,4-pentadiynyl or 2,4-pentadiynyl having at least one triple bond in any position, having 2 to 5 carbon atoms Examples include straight-chain or branched alkynyl groups.
(C 2 -C 4 )-Alkenyl is, for example, vinyl (also simply referred to as ethenyl), allyl (also simply referred to as 2-propenyl), 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1,3-butadien-2-yl, 1-methyl-1-propenyl, 2-buten-2-yl, 3-buten-2-yl, 2-methyl-2-propenyl or 3- Examples include straight-chain or branched alkenyl groups having 2 to 4 carbon atoms and having at least one double bond at any position, such as buten-3-yl. Furthermore, the alkenyl also includes allenyl groups having one integrated double bond, such as 1,2-propadienyl, 1,2-butadienyl, or 2,3-butadienyl. Examples of (C 2 -C 3 )-alkenyl include straight-chain or branched alkenyl groups having 2 to 3 carbon atoms, such as vinyl, allyl, 1-propenyl, isopropenyl, and the like. In addition, if there is a geometric isomer, it may be only one of the E-form or the Z-form, or a mixture of the E-form and the Z-form in any ratio, and there are no particular limitations as long as the number of carbon atoms is within the specified range. It never happens.
(C 3 -C 4 )-cycloalkyl includes, for example, a cycloalkyl group having 3 to 4 carbon atoms such as cyclopropyl or cyclobutyl. Examples of the (C 3 )-cycloalkyl moiety include a cycloalkyl group having 3 carbon atoms such as cyclopropyl.
Further, the (C 3 -C 6 )-cycloalkyloxy moiety includes, for example, a cycloalkyloxy group having 3 to 6 carbon atoms such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy. .
(C2-C5)-アルキニルは、例えば、エチニル、1-プロピニル、プロパルギル(単に2-プロピニルともいう)、1-ブチニル、2-ブチニル、3-ブチニル、1-メチル-2-プロピニル、1,3-ブタジイニル、1-ペンチニル、2-ペンチニル、3-ペンチニル、4-ペンチニル、3-メチル-1-ブチニル、3-ペンチン-2-イル、4-ペンチン-3-イル、4-ペンチン-2-イル、2-メチル-3-ブチニル、1,3-ペンタジイニル、1,4-ペンタジイニル又は2,4-ペンタジイニル等の任意の位置に少なくとも1つの三重結合を有する、炭素原子数2~5個の直鎖又は分岐鎖状のアルキニル基が挙げられる。
(C2-C4)-アルケニルは、例えば、ビニル(単にエテニルともいう)、アリル(単に2-プロペニルともいう)、1-プロペニル、イソプロペニル、1-ブテニル、2-ブテニル、3-ブテニル、1,3-ブタジエニル、1,3-ブタジエン-2-イル、1-メチル-1-プロペニル、2-ブテン-2-イル、3-ブテン-2-イル、2-メチル-2-プロペニル又は3-ブテン-3-イル等の任意の位置に少なくとも1つの二重結合を有する、炭素原子数2~4個の直鎖又は分岐鎖状のアルケニル基が挙げられる。さらに、前記アルケニルには、1つの集積二重結合を有するアレニル基も含み、例えば、1,2-プロパジエニル、1,2-ブタジエニル、又は2,3-ブタジエニルが挙げられる。(C2-C3)-アルケニルは、例えば、ビニル、アリル、1-プロペニル又はイソプロペニル等のような直鎖又は分岐鎖状の炭素原子数2~3個のアルケニル基が挙げられる。また、幾何異性体がある場合、E体又はZ体のどちらか一方のみ、或いはE体とZ体との任意の割合の混合物であり、指定される炭素数の範囲であれば、特に限定されることはない。
(C3-C4)-シクロアルキルは、例えば、シクロプロピル又はシクロブチルのような炭素原子数3~4個のシクロアルキル基が挙げられる。(C3)-シクロアルキル部分は、例えば、シクロプロピルのような炭素原子数3個のシクロアルキル基が挙げられる。
また、(C3-C6)-シクロアルキルオキシ部分は、例えば、シクロプロピルオキシ、シクロブチルオキシ、シクロペンチルオキシ又はシクロへキシルオキシのような炭素原子数3~6個のシクロアルキルオキシ基が挙げられる。 Examples of (C 1 -C 3 )-alkyl include straight-chain or branched alkyl groups having 1 to 3 carbon atoms, such as methyl, ethyl, normal propyl, or isopropyl. (C 1 -C 2 )-alkyl includes, for example, a straight-chain alkyl group having 1 to 2 carbon atoms such as methyl or ethyl. A (C 1 -C 4 )-alkyl moiety is a straight-chain or branched chain having 1 to 4 carbon atoms, such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tertiary-butyl. Examples include chain alkyl groups.
(C 2 -C 5 )-Alkynyl is, for example, ethynyl, 1-propynyl, propargyl (also simply referred to as 2-propynyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1 , 3-butadiynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 3-pentyn-2-yl, 4-pentyn-3-yl, 4-pentyn-2 -yl, 2-methyl-3-butynyl, 1,3-pentadiynyl, 1,4-pentadiynyl or 2,4-pentadiynyl having at least one triple bond in any position, having 2 to 5 carbon atoms Examples include straight-chain or branched alkynyl groups.
(C 2 -C 4 )-Alkenyl is, for example, vinyl (also simply referred to as ethenyl), allyl (also simply referred to as 2-propenyl), 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1,3-butadien-2-yl, 1-methyl-1-propenyl, 2-buten-2-yl, 3-buten-2-yl, 2-methyl-2-propenyl or 3- Examples include straight-chain or branched alkenyl groups having 2 to 4 carbon atoms and having at least one double bond at any position, such as buten-3-yl. Furthermore, the alkenyl also includes allenyl groups having one integrated double bond, such as 1,2-propadienyl, 1,2-butadienyl, or 2,3-butadienyl. Examples of (C 2 -C 3 )-alkenyl include straight-chain or branched alkenyl groups having 2 to 3 carbon atoms, such as vinyl, allyl, 1-propenyl, isopropenyl, and the like. In addition, if there is a geometric isomer, it may be only one of the E-form or the Z-form, or a mixture of the E-form and the Z-form in any ratio, and there are no particular limitations as long as the number of carbon atoms is within the specified range. It never happens.
(C 3 -C 4 )-cycloalkyl includes, for example, a cycloalkyl group having 3 to 4 carbon atoms such as cyclopropyl or cyclobutyl. Examples of the (C 3 )-cycloalkyl moiety include a cycloalkyl group having 3 carbon atoms such as cyclopropyl.
Further, the (C 3 -C 6 )-cycloalkyloxy moiety includes, for example, a cycloalkyloxy group having 3 to 6 carbon atoms such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy. .
(C1-C3)-ハロアルキルは、例えば、フルオロメチル、ジフルオロメチル、トリフルオロメチル、クロロメチル、ジクロロメチル、トリクロロメチル、クロロジフルオロメチル、ジクロロフルオロメチル、クロロフルオロメチル、1-フルオロエチル、2-フルオロエチル、1,1-ジフルオロエチル、2,2-ジフルオロエチル、2,2,2-トリフルオロエチル、パーフルオロエチル、1-クロロエチル、2-クロロエチル、1,1-ジクロロエチル、2,2-ジクロロエチル、2,2,2-トリクロロエチル、1-クロロ-1-フルオロエチル、2-クロロ-2-フルオロエチル、1-フルオロプロピル、2-フルオロプロピル、1-フルオロ-2-プロピル、3-フルオロプロピル、2-フルオロ-2-プロピル、1,1-ジフルオロプロピル、2,2-ジフルオロプロピル、3,3-ジフルオロプロピル、3,3,3-トリフルオロプロピル、パーフルオロプロピル、パーフルオロイソプロピル、2,2,3,3,3-ペンタフルオロプロピル又は1,1,1,3,3,3-ヘキサフルオロイソプロピル等の1~7個の同一のまたは異なるハロゲン原子により部分的または完全に置換された炭素原子数1~3個の直鎖状又は分岐鎖状のアルキル基が挙げられる。(C1)-ハロアルキルは、例えば、フルオロメチル、ジフルオロメチル、トリフルオロメチル、クロロメチル、ジクロロメチル、トリクロロメチル、クロロジフルオロメチル、ジクロロフルオロメチル又はクロロフルオロメチル等の1~3個の同一の又は異なるハロゲン原子より部分的または完全に置換された炭素原子数1個のアルキル基が挙げられる。
(C2-C4)-ハロアルケニルは、例えば、2-フルオロビニル、2,2-ジフルオロビニル、トリフルオロビニル、2-クロロビニル、2,2-ジクロロビニル、2-ブロモビニル、2,2-ジブロモビニル、3-フルオロアリル、3,3-ジフルオロアリル、2,3,3-トリフルオロアリル、3,3-ジフルオロ-1-プロペニル、3,3,3-トリフルオロ-1-プロペニル、3-クロロアリル、3,3-ジクロロアリル、3,3-ジクロロ-1-プロペニル、3,3,3-トリクロロ-1-プロペニル、3,3-ジクロロ-3-フルオロ-1-プロペニル、3-クロロ-3,3-ジフルオロ-1-プロペニル、3-ブロモアリル、3,3-ジブロモアリル、3-フルオロ-2-プロペン-2-イル、3,3-ジフルオロ-2-プロペン-2-イル、3-クロロ-2-プロペン-2-イル、3,3-ジクロロ-2-プロペン-2-イル、3-ブロモ-2-プロペン-2-イル、3,3-ジブロモ-2-プロペン-2-イル、4,4,4-トリフルオロ-1-ブテニル、4,4,4-トリフルオロ-2-ブテニル、4,4-ジフルオロ-3-ブテニル、4,4-ジフルオロ-3-ブテン-2-イル、4-フルオロ-3-ブテン-3-イル、4,4-ジフルオロ-3-ブテン-3-イル、4-クロロ-3-ブテン-3-イル、4,4-ジクロロ-3-ブテン-3-イル、4-ブロモ-3-ブテン-3-イル、4,4-ジブロモ-3-ブテン-3-イル、3-フルオロ-2-ブテン-2-イル、3-クロロ-2-ブテン-2-イル又は3-ブロモ-2-ブテン-2-イル等の任意の位置に少なくとも1つの二重結合を有する、1個又は2個以上の同一の又は異なるハロゲン原子で置換された炭素原子数2~4個の直鎖状又は分岐鎖状のアルケニル基が挙げられる。(C2-C3)-ハロアルケニルは、例えば、2-フルオロビニル、2,2-ジフルオロビニル、トリフルオロビニル、2-クロロビニル、2,2-ジクロロビニル、2-ブロモビニル、2,2-ジブロモビニル、3-フルオロアリル、3,3-ジフルオロアリル、2,3,3-トリフルオロアリル、3,3-ジフルオロ-1-プロペニル、3,3,3-トリフルオロ-1-プロペニル、3-クロロアリル、3,3-ジクロロアリル、3,3-ジクロロ-1-プロペニル、3,3,3-トリクロロ-1-プロペニル、3,3-ジクロロ-3-フルオロ-1-プロペニル、3-クロロ-3,3-ジフルオロ-1-プロペニル、3-ブロモアリル、3,3-ジブロモアリル、2-フルオロ-1-メチルビニル、2,2-ジフルオロ-1-メチルビニル、2-クロロ-1-メチルビニル、2,2-ジクロロ-1-メチルビニル、2-ブロモ-1-メチルビニル又は2,2-ジブロモ-1-メチルビニル等の任意の位置に少なくとも1つの二重結合を有する、1個又は2個以上の同一の又は異なるハロゲン原子で置換された炭素原子数2~3個の直鎖状又は分岐鎖状のアルケニル基が挙げられる。また、幾何異性体がある場合、E体又はZ体のどちらか一方のみ、或いはE体とZ体との任意の割合の混合物であり、指定される炭素数の範囲であれば、特に限定されることはない。 (C 1 -C 3 )-Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 1-fluoroethyl, 2 -Fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, perfluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2 -dichloroethyl, 2,2,2-trichloroethyl, 1-chloro-1-fluoroethyl, 2-chloro-2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 1-fluoro-2-propyl, 3 -Fluoropropyl, 2-fluoro-2-propyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, perfluoropropyl, perfluoroisopropyl , 2,2,3,3,3-pentafluoropropyl or 1,1,1,3,3,3-hexafluoroisopropyl, partially or completely substituted by 1 to 7 identical or different halogen atoms Examples include straight-chain or branched alkyl groups having 1 to 3 carbon atoms. (C 1 )-Haloalkyl is, for example, 1 to 3 identical or Mention may be made of alkyl groups having one carbon atom that are partially or completely substituted with different halogen atoms.
(C 2 -C 4 )-Haloalkenyl is, for example, 2-fluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 2-chlorovinyl, 2,2-dichlorovinyl, 2-bromovinyl, 2,2- Dibromovinyl, 3-fluoroallyl, 3,3-difluoroallyl, 2,3,3-trifluoroallyl, 3,3-difluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 3- Chloroallyl, 3,3-dichloroallyl, 3,3-dichloro-1-propenyl, 3,3,3-trichloro-1-propenyl, 3,3-dichloro-3-fluoro-1-propenyl, 3-chloro-3 , 3-difluoro-1-propenyl, 3-bromoallyl, 3,3-dibromoallyl, 3-fluoro-2-propen-2-yl, 3,3-difluoro-2-propen-2-yl, 3-chloro- 2-propen-2-yl, 3,3-dichloro-2-propen-2-yl, 3-bromo-2-propen-2-yl, 3,3-dibromo-2-propen-2-yl, 4, 4,4-trifluoro-1-butenyl, 4,4,4-trifluoro-2-butenyl, 4,4-difluoro-3-butenyl, 4,4-difluoro-3-buten-2-yl, 4- Fluoro-3-buten-3-yl, 4,4-difluoro-3-buten-3-yl, 4-chloro-3-buten-3-yl, 4,4-dichloro-3-buten-3-yl, 4-bromo-3-buten-3-yl, 4,4-dibromo-3-buten-3-yl, 3-fluoro-2-buten-2-yl, 3-chloro-2-buten-2-yl or 3-bromo-2-buten-2-yl, etc., having at least one double bond at any position and having 2 to 4 carbon atoms substituted with one or more of the same or different halogen atoms Examples include straight-chain or branched alkenyl groups. (C 2 -C 3 )-Haloalkenyl is, for example, 2-fluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 2-chlorovinyl, 2,2-dichlorovinyl, 2-bromovinyl, 2,2- Dibromovinyl, 3-fluoroallyl, 3,3-difluoroallyl, 2,3,3-trifluoroallyl, 3,3-difluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 3- Chloroallyl, 3,3-dichloroallyl, 3,3-dichloro-1-propenyl, 3,3,3-trichloro-1-propenyl, 3,3-dichloro-3-fluoro-1-propenyl, 3-chloro-3 , 3-difluoro-1-propenyl, 3-bromoallyl, 3,3-dibromoallyl, 2-fluoro-1-methylvinyl, 2,2-difluoro-1-methylvinyl, 2-chloro-1-methylvinyl, 2 , 2-dichloro-1-methylvinyl, 2-bromo-1-methylvinyl, or 2,2-dibromo-1-methylvinyl having at least one double bond at any position, one or more. Examples include straight-chain or branched alkenyl groups having 2 to 3 carbon atoms substituted with the same or different halogen atoms. In addition, if there is a geometric isomer, it may be only one of the E-form or the Z-form, or a mixture of the E-form and the Z-form in any ratio, and there are no particular limitations as long as the number of carbon atoms is within the specified range. It never happens.
(C2-C4)-ハロアルケニルは、例えば、2-フルオロビニル、2,2-ジフルオロビニル、トリフルオロビニル、2-クロロビニル、2,2-ジクロロビニル、2-ブロモビニル、2,2-ジブロモビニル、3-フルオロアリル、3,3-ジフルオロアリル、2,3,3-トリフルオロアリル、3,3-ジフルオロ-1-プロペニル、3,3,3-トリフルオロ-1-プロペニル、3-クロロアリル、3,3-ジクロロアリル、3,3-ジクロロ-1-プロペニル、3,3,3-トリクロロ-1-プロペニル、3,3-ジクロロ-3-フルオロ-1-プロペニル、3-クロロ-3,3-ジフルオロ-1-プロペニル、3-ブロモアリル、3,3-ジブロモアリル、3-フルオロ-2-プロペン-2-イル、3,3-ジフルオロ-2-プロペン-2-イル、3-クロロ-2-プロペン-2-イル、3,3-ジクロロ-2-プロペン-2-イル、3-ブロモ-2-プロペン-2-イル、3,3-ジブロモ-2-プロペン-2-イル、4,4,4-トリフルオロ-1-ブテニル、4,4,4-トリフルオロ-2-ブテニル、4,4-ジフルオロ-3-ブテニル、4,4-ジフルオロ-3-ブテン-2-イル、4-フルオロ-3-ブテン-3-イル、4,4-ジフルオロ-3-ブテン-3-イル、4-クロロ-3-ブテン-3-イル、4,4-ジクロロ-3-ブテン-3-イル、4-ブロモ-3-ブテン-3-イル、4,4-ジブロモ-3-ブテン-3-イル、3-フルオロ-2-ブテン-2-イル、3-クロロ-2-ブテン-2-イル又は3-ブロモ-2-ブテン-2-イル等の任意の位置に少なくとも1つの二重結合を有する、1個又は2個以上の同一の又は異なるハロゲン原子で置換された炭素原子数2~4個の直鎖状又は分岐鎖状のアルケニル基が挙げられる。(C2-C3)-ハロアルケニルは、例えば、2-フルオロビニル、2,2-ジフルオロビニル、トリフルオロビニル、2-クロロビニル、2,2-ジクロロビニル、2-ブロモビニル、2,2-ジブロモビニル、3-フルオロアリル、3,3-ジフルオロアリル、2,3,3-トリフルオロアリル、3,3-ジフルオロ-1-プロペニル、3,3,3-トリフルオロ-1-プロペニル、3-クロロアリル、3,3-ジクロロアリル、3,3-ジクロロ-1-プロペニル、3,3,3-トリクロロ-1-プロペニル、3,3-ジクロロ-3-フルオロ-1-プロペニル、3-クロロ-3,3-ジフルオロ-1-プロペニル、3-ブロモアリル、3,3-ジブロモアリル、2-フルオロ-1-メチルビニル、2,2-ジフルオロ-1-メチルビニル、2-クロロ-1-メチルビニル、2,2-ジクロロ-1-メチルビニル、2-ブロモ-1-メチルビニル又は2,2-ジブロモ-1-メチルビニル等の任意の位置に少なくとも1つの二重結合を有する、1個又は2個以上の同一の又は異なるハロゲン原子で置換された炭素原子数2~3個の直鎖状又は分岐鎖状のアルケニル基が挙げられる。また、幾何異性体がある場合、E体又はZ体のどちらか一方のみ、或いはE体とZ体との任意の割合の混合物であり、指定される炭素数の範囲であれば、特に限定されることはない。 (C 1 -C 3 )-Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 1-fluoroethyl, 2 -Fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, perfluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2 -dichloroethyl, 2,2,2-trichloroethyl, 1-chloro-1-fluoroethyl, 2-chloro-2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 1-fluoro-2-propyl, 3 -Fluoropropyl, 2-fluoro-2-propyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, perfluoropropyl, perfluoroisopropyl , 2,2,3,3,3-pentafluoropropyl or 1,1,1,3,3,3-hexafluoroisopropyl, partially or completely substituted by 1 to 7 identical or different halogen atoms Examples include straight-chain or branched alkyl groups having 1 to 3 carbon atoms. (C 1 )-Haloalkyl is, for example, 1 to 3 identical or Mention may be made of alkyl groups having one carbon atom that are partially or completely substituted with different halogen atoms.
(C 2 -C 4 )-Haloalkenyl is, for example, 2-fluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 2-chlorovinyl, 2,2-dichlorovinyl, 2-bromovinyl, 2,2- Dibromovinyl, 3-fluoroallyl, 3,3-difluoroallyl, 2,3,3-trifluoroallyl, 3,3-difluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 3- Chloroallyl, 3,3-dichloroallyl, 3,3-dichloro-1-propenyl, 3,3,3-trichloro-1-propenyl, 3,3-dichloro-3-fluoro-1-propenyl, 3-chloro-3 , 3-difluoro-1-propenyl, 3-bromoallyl, 3,3-dibromoallyl, 3-fluoro-2-propen-2-yl, 3,3-difluoro-2-propen-2-yl, 3-chloro- 2-propen-2-yl, 3,3-dichloro-2-propen-2-yl, 3-bromo-2-propen-2-yl, 3,3-dibromo-2-propen-2-yl, 4, 4,4-trifluoro-1-butenyl, 4,4,4-trifluoro-2-butenyl, 4,4-difluoro-3-butenyl, 4,4-difluoro-3-buten-2-yl, 4- Fluoro-3-buten-3-yl, 4,4-difluoro-3-buten-3-yl, 4-chloro-3-buten-3-yl, 4,4-dichloro-3-buten-3-yl, 4-bromo-3-buten-3-yl, 4,4-dibromo-3-buten-3-yl, 3-fluoro-2-buten-2-yl, 3-chloro-2-buten-2-yl or 3-bromo-2-buten-2-yl, etc., having at least one double bond at any position and having 2 to 4 carbon atoms substituted with one or more of the same or different halogen atoms Examples include straight-chain or branched alkenyl groups. (C 2 -C 3 )-Haloalkenyl is, for example, 2-fluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 2-chlorovinyl, 2,2-dichlorovinyl, 2-bromovinyl, 2,2- Dibromovinyl, 3-fluoroallyl, 3,3-difluoroallyl, 2,3,3-trifluoroallyl, 3,3-difluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 3- Chloroallyl, 3,3-dichloroallyl, 3,3-dichloro-1-propenyl, 3,3,3-trichloro-1-propenyl, 3,3-dichloro-3-fluoro-1-propenyl, 3-chloro-3 , 3-difluoro-1-propenyl, 3-bromoallyl, 3,3-dibromoallyl, 2-fluoro-1-methylvinyl, 2,2-difluoro-1-methylvinyl, 2-chloro-1-methylvinyl, 2 , 2-dichloro-1-methylvinyl, 2-bromo-1-methylvinyl, or 2,2-dibromo-1-methylvinyl having at least one double bond at any position, one or more. Examples include straight-chain or branched alkenyl groups having 2 to 3 carbon atoms substituted with the same or different halogen atoms. In addition, if there is a geometric isomer, it may be only one of the E-form or the Z-form, or a mixture of the E-form and the Z-form in any ratio, and there are no particular limitations as long as the number of carbon atoms is within the specified range. It never happens.
少なくとも1個のZで置換された(C1-C3)-アルキルは、例えばシアノメチル、1-シアノエチル、2-シアノエチル、1-シアノプロピル、2-シアノプロピル、3-シアノプロピル、ジシアノメチル、2,2-ジシアノエチル、メトキシメチル、エトキシメチル、プロポキシメチル、イソプロポキシメチル、1-メトキシエチル、1-エトキシエチル、1-プロポキシエチル、1-イソプロポキシエチル、2-メトキシエチル、2-エトキシエチル、2-プロポキシエチル、2-イソプロポキシエチル、1-メトキシプロピル、1-エトキシプロピル、1-プロポキシプロピル、1-イソプロポキシプロピル、2-メトキシプロピル、2-エトキシプロピル、2-プロポキシプロピル、2-イソプロポキシプロピル、3-メトキシプロピル、3-エトキシプロピル、3-プロポキシプロピル、3-イソプロポキシプロピル、1-メトキシ-2-プロピル、1-エトキシ-2-プロピル、1-プロポキシ-2-プロピル、1-イソプロポキシ-2-プロピル、2-メトキシ-2-プロピル、2-エトキシ-2-プロピル、2-プロポキシ-2-プロピル、2-イソプロポキシ-2-プロピル、ジメトキシメチル、ジエトキシメチル、2,2-ジメトキシエチル、2,2-ジエトキシエチル、メチルチオメチル、エチルチオメチル、プロピルチオメチル、イソプロピルチオメチル、1-メチルチオエチル、1-エチルチオエチル、1-プロピルチオエチル、1-イソプロピルチオエチル、2-メチルチオエチル、2-エチルチオエチル、2-プロピルチオエチル、2-イソプロピルチオエチル、1-メチルチオプロピル、1-エチルチオプロピル、1-プロピルチオプロピル、1-イソプロピルチオプロピル、2-メチルチオプロピル、2-エチルチオプロピル、2-プロピルチオプロピル、2-イソプロピルチオプロピル、3-メチルチオプロピル、3-エチルチオプロピル、3-プロピルチオプロピル、3-イソプロピルチオプロピル、1-メチルチオ-2-プロピル、1-エチルチオ-2-プロピル、1-プロピルチオ-2-プロピル、1-イソプロピルチオ-2-プロピル、2-メチルチオ-2-プロピル、2-エチルチオ-2-プロピル、2-プロピルチオ-2-プロピル、2-イソプロピルチオ-2-プロピル、ジメチルチオメチル、ジエチルチオメチル、2,2-ジメチルチオエチル、2,2-ジエチルチオエチル、シクロプロピルメチル、1-シクロプロピルエチル、2-シクロプロピルエチル、1-シクロプロピルプロピル、2-シクロプロピルプロピル、3-シクロプロピルプロピル、1-シクロプロピル-2-プロピル、2-シクロプロピル-2-プロピル、フルオロメチル、ジフルオロメチル、トリフルオロメチル、クロロメチル、ジクロロメチル、トリクロロメチル、クロロジフルオロメチル、ジクロロフルオロメチル、クロロフルオロメチル、1-フルオロエチル、2-フルオロエチル、1,1-ジフルオロエチル、2,2-ジフルオロエチル、2,2,2-トリフルオロエチル、パーフルオロエチル、1-クロロエチル、2-クロロエチル、1,1-ジクロロエチル、2,2-ジクロロエチル、2,2,2-トリクロロエチル、1-クロロ-1-フルオロエチル、2-クロロ-2-フルオロエチル、1-フルオロプロピル、2-フルオロプロピル、3-フルオロプロピル、2-フルオロ-2-プロピル、1,1-ジフルオロプロピル、2,2-ジフルオロプロピル、3,3-ジフルオロプロピル、3,3,3-トリフルオロプロピル、パーフルオロプロピル、パーフルオロイソプロピル、2,2,3,3,3-ペンタフルオロプロピル、1,1,1,3,3,3-ヘキサフルオロイソプロピル、メチルカルボニルメチル、エチルカルボニルメチル、プロピルカルボニルメチル、イソプロピルカルボニルメチル、ブチルカルボニルメチル、イソブチルカルボニルメチル、セカンダリーブチルカルボニルメチル、ターシャリーブチルカルボニルメチル、2-(メチルカルボニル)エチル、2-(エチルカルボニル)エチル、2-(プロピルカルボニル)エチル、2-(イソプロピルカルボニル)エチル、2-(ブチルカルボニル)エチル、2-(イソブチルカルボニル)エチル、2-(セカンダリーブチル)エチル、2-(ターシャリーブチルカルボニル)エチル、1-(メチルカルボニル)エチル、1-(エチルカルボニル)エチル、1-(プロピルカルボニル)エチル、1-(イソプロピルカルボニル)エチル、1-(ブチルカルボニル)エチル、1-(イソブチルカルボニル)エチル、1-(セカンダリーブチルカルボニル)エチル、1-(ターシャリーブチルカルボニル)エチル、3-(メチルカルボニル)プロピル、3-(エチルカルボニル)プロピル、3-(プロピルカルボニル)プロピル、3-(イソプロピルカルボニル)プロピル、3-(ブチルカルボニル)プロピル、3-(イソブチルカルボニル)プロピル、3-(セカンダリーブチルカルボニル)プロピル、3-(ターシャリーブチルカルボニル)プロピル、2-(メチルカルボニル)プロピル、2-(エチルカルボニル)プロピル、2-(プロピルカルボニル)プロピル、2-(イソプロピルカルボニル)プロピル、2-(ブチルカルボニル)プロピル、2-(イソブチルカルボニル)プロピル、2-(セカンダリーブチルカルボニル)プロピル、2-(ターシャリーブチルカルボニル)プロピル、1-(メチルカルボニル)プロピル、1-(エチルカルボニル)プロピル、1-(プロピルカルボニル)プロピル、1-(イソプロピルカルボニル)プロピル、1-(ブチルカルボニル)プロピル、1-(イソブチルカルボニル)プロピル、1-(セカンダリーブチルカルボニル)プロピル、1-(ターシャリーブチルカルボニル)プロピル、1-(メチルカルボニル)-2-プロピル、1-(エチルカルボニル)-2-プロピル、1-(プロピルカルボニル)-2-プロピル、1-(イソプロピルカルボニル)-2-プロピル、1-(ブチルカルボニル)-2-プロピル、1-(イソブチルカルボニル)-2-プロピル、1-(セカンダリーブチルカルボニル)-2-プロピル、1-(ターシャリーブチルカルボニル)-2-プロピル、2-(メチルカルボニル)-2-プロピル、2-(エチルカルボニル)-2-プロピル、2-(プロピルカルボニル)-2-プロピル、2-(イソプロピルカルボニル)-2-プロピル、2-(ブチルカルボニル)-2-プロピル、2-(イソブチルカルボニル)-2-プロピル、2-(セカンダリーブチルカルボニル)-2-プロピル、2-(ターシャリーブチルカルボニル)-2-プロピル、メトキシカルボニルメチル、エトキシカルボニルメチル、プロポキシカルボニルメチル、イソプロポキシカルボニルメチル、ブトキシカルボニルメチル、イソブトキシカルボニルメチル、セカンダリーブトキシカルボニルメチル、ターシャリーブトキシカルボニルメチル、2-(メトキシカルボニル)エチル、2-(エトキシカルボニル)エチル、2-(プロポキシカルボニル)エチル、2-(イソプロポキシカルボニル)エチル、2-(ブトキシカルボニル)エチル、2-(イソブトキシカルボニル)エチル、2-(セカンダリーブトキシカルボニル)エチル、2-(ターシャリーブトキシカルボニル)エチル、1-(メトキシカルボニル)エチル、1-(エトキシカルボニル)エチル、1-(プロポキシカルボニル)エチル、1-(イソプロポキシカルボニル)エチル、1-(ブトキシカルボニル)エチル、1-(イソブトキシカルボニル)エチル、1-(セカンダリーブトキシカルボニル)エチル、1-(ターシャリーブトキシカルボニル)エチル、3-(メトキシカルボニル)プロピル、3-(エトキシカルボニル)プロピル、3-(プロポキシカルボニル)プロピル、3-(イソプロポキシカルボニル)プロピル、3-(ブトキシカルボニル)プロピル、3-(イソブトキシカルボニル)プロピル、3-(セカンダリーブトキシカルボニル)プロピル、3-(ターシャリーブトキシカルボニル)プロピル、2-(メトキシカルボニル)プロピル、2-(エトキシカルボニル)プロピル、2-(プロポキシカルボニル)プロピル、2-(イソプロポキシカルボニル)プロピル、2-(ブトキシカルボニル)プロピル、2-(イソブトキシカルボニル)プロピル、2-(セカンダリーブトキシカルボニル)プロピル、2-(ターシャリーブトキシカルボニル)プロピル、1-(メトキシカルボニル)プロピル、1-(エトキシカルボニル)プロピル、1-(プロポキシカルボニル)プロピル、1-(イソプロポキシカルボニル)プロピル、1-(ブトキシカルボニル)プロピル、1-(イソブトキシカルボニル)プロピル、1-(セカンダリーブトキシカルボニル)プロピル、1-(ターシャリーブトキシカルボニル)プロピル、1-(メトキシカルボニル)-2-プロピル、1-(エトキシカルボニル)-2-プロピル、1-(プロポキシカルボニル)-2-プロピル、1-(イソプロポキシカルボニル)-2-プロピル、1-(ブトキシカルボニル)-2-プロピル、1-(イソブトキシカルボニル)-2-プロピル、1-(セカンダリーブトキシカルボニル)-2-プロピル、1-(ターシャリーブトキシカルボニル)-2-プロピル、2-(メトキシカルボニル)-2-プロピル、2-(エトキシカルボニル)-2-プロピル、2-(プロポキシカルボニル)-2-プロピル、2-(イソプロポキシカルボニル)-2-プロピル、2-(ブトキシカルボニル)-2-プロピル、2-(イソブトキシカルボニル)-2-プロピル、2-(セカンダリーブトキシカルボニル)-2-プロピル、2-(ターシャリーブトキシカルボニル)-2-プロピル、シクロプロピルオキシカルボニルメチル、シクロブチルオキシカルボニルメチル、シクロペンチルオキシカルボニルメチル、シクロヘキシルオキシカルボニルメチル、2-(シクロプロピルオキシカルボニル)エチル、2-(シクロブチルオキシカルボニル)エチル、2-(シクロペンチルオキシカルボニル)エチル、2-(シクロヘキシルオキシカルボニル)エチル、1-(シクロプロピルオキシカルボニル)エチル、1-(シクロブチルオキシカルボニル)エチル、1-(シクロペンチルオキシカルボニル)エチル、1-(シクロヘキシルオキシカルボニル)エチル、3-(シクロプロピルオキシカルボニル)プロピル、3-(シクロブチルオキシカルボニル)プロピル、3-(シクロペンチルオキシカルボニル)プロピル、3-(シクロヘキシルオキシカルボニル)プロピル、2-(シクロプロピルオキシカルボニル)プロピル、2-(シクロブチルオキシカルボニル)プロピル、2-(シクロペンチルオキシカルボニル)プロピル、2-(シクロヘキシルオキシカルボニル)プロピル、1-(シクロプロピルオキシカルボニル)プロピル、1-(シクロブチルオキシカルボニル)プロピル、1-(シクロペンチルオキシカルボニル)プロピル、1-(シクロヘキシルオキシカルボニル)プロピル、1-メチル-1-(シクロプロピルオキシカルボニル)エチル、1-メチル-1-(シクロブチルオキシカルボニル)エチル、1-メチル-1-(シクロペンチルオキシカルボニル)エチル、1-メチル-1-(シクロヘキシルオキシカルボニル)エチル、1-(シクロプロピルオキシカルボニル)-2-プロピル、1-(シクロブチルオキシカルボニル)-2-プロピル、1-(シクロペンチルオキシカルボニル)-2-プロピル、1-(シクロヘキシルオキシカルボニル)-2-プロピル、2-(シクロプロピルオキシカルボニル)-2-プロピル、2-(シクロブチルオキシカルボニル)-2-プロピル、2-(シクロペンチルオキシカルボニル)-2-プロピル、2-(シクロヘキシルオキシカルボニル)-2-プロピル、フェノキシカルボニルメチル、2-フェノキシカルボニルエチル、1-フェノキシカルボニルエチル、3-フェノキシカルボニルプロピル、2-フェノキシカルボニルプ
ロピル、1-フェノキシカルボニルプロピル、1-(フェノキシカルボニル)-2-プロピル、2-(フェノキシカルボニル)-2-プロピル、ベンジルオキシカルボニルメチル、2-ベンジルオキシカルボニルエチル、1-ベンジルオキシカルボニルエチル、3-ベンジルオキシカルボニルプロピル、2-ベンジルオキシカルボニルプロピル、1-ベンジルオキシカルボニルプロピル、1-(ベンジルオキシカルボニル)-2-プロピル、2-(ベンジルオキシカルボニル)-2-プロピル、カルボキシメチル、2-カルボキシエチル、1-カルボキシエチル、3-カルボキシプロピル、2-カルボキシプロピル、1-カルボキシプロピル、1-カルボキシ-2-プロピル、2-カルボキシ-2-プロピル、ヒドロキシメチル、2-ヒドロキシエチル、1-ヒドロキシエチル、3-ヒドロキシプロピル、2-ヒドロキシプロピル、1-ヒドロキシプロピル、1-ヒドロキシ-2-プロピル、2-ヒドロキシ-2-プロピル、トリメチルシリルオキシメチル、ジメチルエチルシリルオキシメチル、ジメチルプロピルシリルオキシメチル、ジメチルイソプロピルシリルオキシメチル、ブチルジメチルシリルオキシメチル、(ターシャリーブチル)ジメチルシリルオキシメチル、トリエチルシリルオキシメチル、ジエチルイソプロピルシリルオキシメチル、トリイソプロピルシリルオキシメチル、トリプロピルシリルオキシメチル、トリブチルシリルオキシメチル、2-(トリメチルシリルオキシ)エチル、2-(ジメチルエチルシリルオキシ)エチル、2-(ジメチルプロピルシリルオキシ)エチル、2-(ジメチルイソプロピルシリルオキシ)エチル、2-(ブチルジメチルシリルオキシ)エチル、2-(ターシャリーブチルジメチルシリルオキシ)エチル、2-(トリエチルシリルオキシ)エチル、2-(ジエチルイソプロピルシリルオキシ)エチル、2-(トリイソプロピルシリルオキシ)エチル、2-(トリプロピルシリルオキシ)エチル、2-(トリブチルシリルオキシ)エチル、1-(トリメチルシリルオキシ)エチル、1-(ジメチルエチルシリルオキシ)エチル、1-(ジメチルプロピルシリルオキシ)エチル、1-(ジメチルイソプロピルシリルオキシ)エチル、1-(ブチルジメチルシリルオキシ)エチル、1-(ターシャリーブチルジメチルシリルオキシ)エチル、1-(トリエチルシリルオキシ)エチル、1-(ジエチルイソプロピルシリルオキシ)エチル、1-(トリイソプロピルシリルオキシ)エチル、1-(トリプロピルシリルオキシ)エチル、1-(トリブチルシリルオキシ)エチル、3-(トリメチルシリルオキシ)プロピル、3-(ジメチルエチルシリルオキシ)プロピル、3-(ジメチルプロピルシリルオキシ)プロピル、3-(ジメチルイソプロピルシリルオキシ)プロピル、3-(ブチルジメチルシリルオキシ)プロピル、3-(ターシャリーブチルジメチルシリルオキシ)プロピル、3-(トリエチルシリルオキシ)プロピル、3-(ジエチルイソプロピルシリルオキシ)プロピル、3-(トリイソプロピルシリルオキシ)プロピル、3-(トリプロピルシリルオキシ)プロピル、3-(トリブチルシリルオキシ)プロピル、2-(トリメチルシリルオキシ)プロピル、2-(ジメチルエチルシリルオキシ)プロピル、2-(ジメチルプロピルシリルオキシ)プロピル、2-(ジメチルイソプロピルシリルオキシ)プロピル、2-(ブチルジメチルシリルオキシ)プロピル、2-(ターシャリーブチルジメチルシリルオキシ)プロピル、2-(トリエチルシリルオキシ)プロピル、2-(ジエチルイソプロピルシリルオキシ)プロピル、2-(トリイソプロピルシリルオキシ)プロピル、2-(トリプロピルシリルオキシ)プロピル、2-(トリブチルシリルオキシ)プロピル、1-(トリメチルシリルオキシ)プロピル、1-(ジメチルエチルシリルオキシ)プロピル、1-(ジメチルプロピルシリルオキシ)プロピル、1-(ジメチルイソプロピルシリルオキシ)プロピル、1-(ブチルジメチルシリルオキシ)プロピル、1-(ターシャリーブチルジメチルシリルオキシ)プロピル、1-(トリエチルシリルオキシ)プロピル、1-(ジエチルイソプロピルシリルオキシ)プロピル、1-(トリイソプロピルシリルオキシ)プロピル、1-(トリプロピルシリルオキシ)プロピル、1-(トリブチルシリルオキシ)プロピル、1-(トリメチルシリルオキシ)-2-プロピル、1-(ジメチルエチルシリルオキシ)-2-プロピル、1-(ジメチルプロピルシリルオキシ)-2-プロピル、1-(ジメチルイソプロピルシリルオキシ)-2-プロピル、1-(ブチルジメチルシリルオキシ)-2-プロピル、1-(ターシャリーブチルジメチルシリルオキシ)-2-プロピル、1-(トリエチルシリルオキシ)-2-プロピル、1-(ジエチルイソプロピルシリルオキシ)-2-プロピル、1-(トリイソプロピルシリルオキシ)-2-プロピル、1-(トリプロピルシリルオキシ)-2-プロピル、1-(トリブチルシリルオキシ)-2-プロピル、2-(トリメチルシリルオキシ)-2-プロピル、2-(ジメチルエチルシリルオキシ)-2-プロピル、2-(ジメチルプロピルシリルオキシ)-2-プロピル、2-(ジメチルイソプロピルシリルオキシ)-2-プロピル、2-(ブチルジメチルシリルオキシ)-2-プロピル、2-(ターシャリーブチルジメチルシリルオキシ)-2-プロピル、2-(トリエチルシリルオキシ)-2-プロピル、2-(ジエチルイソプロピルシリルオキシ)-2-プロピル、2-(トリイソプロピルシリルオキシ)-2-プロピル、2-(トリプロピルシリルオキシ)-2-プロピル又は2-(トリブチルシリルオキシ)-2-プロピル等の任意の位置に少なくとも1個のZで置換された炭素原子数1~3個の直鎖状又は分岐鎖状のアルキル基が挙げられる。Zの置換数は1個又は2個以上であってよく、2個以上の場合、Zの種類は同一でも相異なってもよく、Zの種類は同一が好ましい。また、Zの置換位置はいずれの位置であってもよい。 (C 1 -C 3 )-Alkyl substituted with at least one Z is, for example, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, dicyanomethyl, 2 , 2-dicyanoethyl, methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-Propoxyethyl, 2-isopropoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-iso Propoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, 1-methoxy-2-propyl, 1-ethoxy-2-propyl, 1-propoxy-2-propyl, 1- Isopropoxy-2-propyl, 2-methoxy-2-propyl, 2-ethoxy-2-propyl, 2-propoxy-2-propyl, 2-isopropoxy-2-propyl, dimethoxymethyl, diethoxymethyl, 2,2 -dimethoxyethyl, 2,2-diethoxyethyl, methylthiomethyl, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, 1-methylthioethyl, 1-ethylthioethyl, 1-propylthioethyl, 1-isopropylthioethyl, 2-Methylthioethyl, 2-ethylthioethyl, 2-propylthioethyl, 2-isopropylthioethyl, 1-methylthiopropyl, 1-ethylthiopropyl, 1-propylthiopropyl, 1-isopropylthiopropyl, 2-methylthiopropyl , 2-ethylthiopropyl, 2-propylthiopropyl, 2-isopropylthiopropyl, 3-methylthiopropyl, 3-ethylthiopropyl, 3-propylthiopropyl, 3-isopropylthiopropyl, 1-methylthio-2-propyl, 1-ethylthio-2-propyl, 1-propylthio-2-propyl, 1-isopropylthio-2-propyl, 2-methylthio-2-propyl, 2-ethylthio-2-propyl, 2-propylthio-2-propyl, 2 -isopropylthio-2-propyl, dimethylthiomethyl, diethylthiomethyl, 2,2-dimethylthioethyl, 2,2-diethylthioethyl, cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, 1- Cyclopropylpropyl, 2-cyclopropylpropyl, 3-cyclopropylpropyl, 1-cyclopropyl-2-propyl, 2-cyclopropyl-2-propyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, Trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, per Fluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1-chloro-1-fluoroethyl, 2-chloro-2-fluoro Ethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 2-fluoro-2-propyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3, 3-trifluoropropyl, perfluoropropyl, perfluoroisopropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,1,3,3,3-hexafluoroisopropyl, methylcarbonylmethyl, ethylcarbonyl Methyl, propylcarbonylmethyl, isopropylcarbonylmethyl, butylcarbonylmethyl, isobutylcarbonylmethyl, sec-butylcarbonylmethyl, tert-butylcarbonylmethyl, 2-(methylcarbonyl)ethyl, 2-(ethylcarbonyl)ethyl, 2-(propylcarbonyl) ) Ethyl, 2-(isopropylcarbonyl)ethyl, 2-(butylcarbonyl)ethyl, 2-(isobutylcarbonyl)ethyl, 2-(sec-butyl)ethyl, 2-(tert-butylcarbonyl)ethyl, 1-(methylcarbonyl) ) Ethyl, 1-(ethylcarbonyl)ethyl, 1-(propylcarbonyl)ethyl, 1-(isopropylcarbonyl)ethyl, 1-(butylcarbonyl)ethyl, 1-(isobutylcarbonyl)ethyl, 1-(secondary butylcarbonyl) Ethyl, 1-(tert-butylcarbonyl)ethyl, 3-(methylcarbonyl)propyl, 3-(ethylcarbonyl)propyl, 3-(propylcarbonyl)propyl, 3-(isopropylcarbonyl)propyl, 3-(butylcarbonyl) Propyl, 3-(isobutylcarbonyl)propyl, 3-(sec-butylcarbonyl)propyl, 3-(tert-butylcarbonyl)propyl, 2-(methylcarbonyl)propyl, 2-(ethylcarbonyl)propyl, 2-(propylcarbonyl) ) propyl, 2-(isopropylcarbonyl)propyl, 2-(butylcarbonyl)propyl, 2-(isobutylcarbonyl)propyl, 2-(sec-butylcarbonyl)propyl, 2-(tert-butylcarbonyl)propyl, 1-(methyl) carbonyl)propyl, 1-(ethylcarbonyl)propyl, 1-(propylcarbonyl)propyl, 1-(isopropylcarbonyl)propyl, 1-(butylcarbonyl)propyl, 1-(isobutylcarbonyl)propyl, 1-(secondary butylcarbonyl) ) propyl, 1-(tert-butylcarbonyl)propyl, 1-(methylcarbonyl)-2-propyl, 1-(ethylcarbonyl)-2-propyl, 1-(propylcarbonyl)-2-propyl, 1-(isopropyl) carbonyl)-2-propyl, 1-(butylcarbonyl)-2-propyl, 1-(isobutylcarbonyl)-2-propyl, 1-(sec-butylcarbonyl)-2-propyl, 1-(tert-butylcarbonyl)- 2-propyl, 2-(methylcarbonyl)-2-propyl, 2-(ethylcarbonyl)-2-propyl, 2-(propylcarbonyl)-2-propyl, 2-(isopropylcarbonyl)-2-propyl, 2- (Butylcarbonyl)-2-propyl, 2-(isobutylcarbonyl)-2-propyl, 2-(sec-butylcarbonyl)-2-propyl, 2-(tert-butylcarbonyl)-2-propyl, methoxycarbonylmethyl, ethoxy Carbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, secondary butoxycarbonylmethyl, tert-butoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2- (Propoxycarbonyl)ethyl, 2-(isopropoxycarbonyl)ethyl, 2-(butoxycarbonyl)ethyl, 2-(isobutoxycarbonyl)ethyl, 2-(sec-butoxycarbonyl)ethyl, 2-(tert-butoxycarbonyl)ethyl , 1-(methoxycarbonyl)ethyl, 1-(ethoxycarbonyl)ethyl, 1-(propoxycarbonyl)ethyl, 1-(isopropoxycarbonyl)ethyl, 1-(butoxycarbonyl)ethyl, 1-(isobutoxycarbonyl)ethyl , 1-(sec-butoxycarbonyl)ethyl, 1-(tert-butoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 3-(ethoxycarbonyl)propyl, 3-(propoxycarbonyl)propyl, 3-(isopropoxycarbonyl) ) propyl, 3-(butoxycarbonyl)propyl, 3-(isobutoxycarbonyl)propyl, 3-(sec-butoxycarbonyl)propyl, 3-(tert-butoxycarbonyl)propyl, 2-(methoxycarbonyl)propyl, 2-( ethoxycarbonyl)propyl, 2-(propoxycarbonyl)propyl, 2-(isopropoxycarbonyl)propyl, 2-(butoxycarbonyl)propyl, 2-(isobutoxycarbonyl)propyl, 2-(secondary butoxycarbonyl)propyl, 2- (tert-butoxycarbonyl)propyl, 1-(methoxycarbonyl)propyl, 1-(ethoxycarbonyl)propyl, 1-(propoxycarbonyl)propyl, 1-(isopropoxycarbonyl)propyl, 1-(butoxycarbonyl)propyl, 1 -(isobutoxycarbonyl)propyl, 1-(secondary butoxycarbonyl)propyl, 1-(tert-butoxycarbonyl)propyl, 1-(methoxycarbonyl)-2-propyl, 1-(ethoxycarbonyl)-2-propyl, 1 -(Propoxycarbonyl)-2-propyl, 1-(isopropoxycarbonyl)-2-propyl, 1-(butoxycarbonyl)-2-propyl, 1-(isobutoxycarbonyl)-2-propyl, 1-(secondary butoxy) carbonyl)-2-propyl, 1-(tert-butoxycarbonyl)-2-propyl, 2-(methoxycarbonyl)-2-propyl, 2-(ethoxycarbonyl)-2-propyl, 2-(propoxycarbonyl)-2 -propyl, 2-(isopropoxycarbonyl)-2-propyl, 2-(butoxycarbonyl)-2-propyl, 2-(isobutoxycarbonyl)-2-propyl, 2-(secondary butoxycarbonyl)-2-propyl, 2-(tert-butoxycarbonyl)-2-propyl, cyclopropyloxycarbonylmethyl, cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 2-(cyclopropyloxycarbonyl)ethyl, 2-(cyclobutyl) oxycarbonyl)ethyl, 2-(cyclopentyloxycarbonyl)ethyl, 2-(cyclohexyloxycarbonyl)ethyl, 1-(cyclopropyloxycarbonyl)ethyl, 1-(cyclobutyloxycarbonyl)ethyl, 1-(cyclopentyloxycarbonyl) Ethyl, 1-(cyclohexyloxycarbonyl)ethyl, 3-(cyclopropyloxycarbonyl)propyl, 3-(cyclobutyloxycarbonyl)propyl, 3-(cyclopentyloxycarbonyl)propyl, 3-(cyclohexyloxycarbonyl)propyl, 2 -(cyclopropyloxycarbonyl)propyl, 2-(cyclobutyloxycarbonyl)propyl, 2-(cyclopentyloxycarbonyl)propyl, 2-(cyclohexyloxycarbonyl)propyl, 1-(cyclopropyloxycarbonyl)propyl, 1-( cyclobutyloxycarbonyl)propyl, 1-(cyclopentyloxycarbonyl)propyl, 1-(cyclohexyloxycarbonyl)propyl, 1-methyl-1-(cyclopropyloxycarbonyl)ethyl, 1-methyl-1-(cyclobutyloxycarbonyl) ) Ethyl, 1-methyl-1-(cyclopentyloxycarbonyl)ethyl, 1-methyl-1-(cyclohexyloxycarbonyl)ethyl, 1-(cyclopropyloxycarbonyl)-2-propyl, 1-(cyclobutyloxycarbonyl) -2-propyl, 1-(cyclopentyloxycarbonyl)-2-propyl, 1-(cyclohexyloxycarbonyl)-2-propyl, 2-(cyclopropyloxycarbonyl)-2-propyl, 2-(cyclobutyloxycarbonyl) -2-propyl, 2-(cyclopentyloxycarbonyl)-2-propyl, 2-(cyclohexyloxycarbonyl)-2-propyl, phenoxycarbonylmethyl, 2-phenoxycarbonylethyl, 1-phenoxycarbonylethyl, 3-phenoxycarbonylpropyl , 2-phenoxycarbonylpropyl, 1-phenoxycarbonylpropyl, 1-(phenoxycarbonyl)-2-propyl, 2-(phenoxycarbonyl)-2-propyl, benzyloxycarbonylmethyl, 2-benzyloxycarbonylethyl, 1-benzyl Oxycarbonylethyl, 3-benzyloxycarbonylpropyl, 2-benzyloxycarbonylpropyl, 1-benzyloxycarbonylpropyl, 1-(benzyloxycarbonyl)-2-propyl, 2-(benzyloxycarbonyl)-2-propyl, carboxy Methyl, 2-carboxyethyl, 1-carboxyethyl, 3-carboxypropyl, 2-carboxypropyl, 1-carboxypropyl, 1-carboxy-2-propyl, 2-carboxy-2-propyl, hydroxymethyl, 2-hydroxyethyl , 1-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 1-hydroxypropyl, 1-hydroxy-2-propyl, 2-hydroxy-2-propyl, trimethylsilyloxymethyl, dimethylethylsilyloxymethyl, dimethylpropylsilyl Oxymethyl, dimethylisopropylsilyloxymethyl, butyldimethylsilyloxymethyl, (tert-butyl)dimethylsilyloxymethyl, triethylsilyloxymethyl, diethylisopropylsilyloxymethyl, triisopropylsilyloxymethyl, tripropylsilyloxymethyl, tributylsilyl Oxymethyl, 2-(trimethylsilyloxy)ethyl, 2-(dimethylethylsilyloxy)ethyl, 2-(dimethylpropylsilyloxy)ethyl, 2-(dimethylisopropylsilyloxy)ethyl, 2-(butyldimethylsilyloxy)ethyl , 2-(tert-butyldimethylsilyloxy)ethyl, 2-(triethylsilyloxy)ethyl, 2-(diethylisopropylsilyloxy)ethyl, 2-(triisopropylsilyloxy)ethyl, 2-(tripropylsilyloxy) Ethyl, 2-(tributylsilyloxy)ethyl, 1-(trimethylsilyloxy)ethyl, 1-(dimethylethylsilyloxy)ethyl, 1-(dimethylpropylsilyloxy)ethyl, 1-(dimethylisopropylsilyloxy)ethyl, 1 -(butyldimethylsilyloxy)ethyl, 1-(tert-butyldimethylsilyloxy)ethyl, 1-(triethylsilyloxy)ethyl, 1-(diethylisopropylsilyloxy)ethyl, 1-(triisopropylsilyloxy)ethyl, 1-(Tripropylsilyloxy)ethyl, 1-(tributylsilyloxy)ethyl, 3-(trimethylsilyloxy)propyl, 3-(dimethylethylsilyloxy)propyl, 3-(dimethylpropylsilyloxy)propyl, 3-( dimethylisopropylsilyloxy)propyl, 3-(butyldimethylsilyloxy)propyl, 3-(tert-butyldimethylsilyloxy)propyl, 3-(triethylsilyloxy)propyl, 3-(diethylisopropylsilyloxy)propyl, 3- (triisopropylsilyloxy)propyl, 3-(tripropylsilyloxy)propyl, 3-(tributylsilyloxy)propyl, 2-(trimethylsilyloxy)propyl, 2-(dimethylethylsilyloxy)propyl, 2-(dimethylpropyl) silyloxy)propyl, 2-(dimethylisopropylsilyloxy)propyl, 2-(butyldimethylsilyloxy)propyl, 2-(tert-butyldimethylsilyloxy)propyl, 2-(triethylsilyloxy)propyl, 2-(diethyl Isopropylsilyloxy)propyl, 2-(triisopropylsilyloxy)propyl, 2-(tripropylsilyloxy)propyl, 2-(tributylsilyloxy)propyl, 1-(trimethylsilyloxy)propyl, 1-(dimethylethylsilyloxy) ) propyl, 1-(dimethylpropylsilyloxy)propyl, 1-(dimethylisopropylsilyloxy)propyl, 1-(butyldimethylsilyloxy)propyl, 1-(tert-butyldimethylsilyloxy)propyl, 1-(triethylsilyl) oxy)propyl, 1-(diethylisopropylsilyloxy)propyl, 1-(triisopropylsilyloxy)propyl, 1-(tripropylsilyloxy)propyl, 1-(tributylsilyloxy)propyl, 1-(trimethylsilyloxy)- 2-propyl, 1-(dimethylethylsilyloxy)-2-propyl, 1-(dimethylpropylsilyloxy)-2-propyl, 1-(dimethylisopropylsilyloxy)-2-propyl, 1-(butyldimethylsilyloxy) )-2-propyl, 1-(tert-butyldimethylsilyloxy)-2-propyl, 1-(triethylsilyloxy)-2-propyl, 1-(diethylisopropylsilyloxy)-2-propyl, 1-(triethylsilyloxy)-2-propyl, isopropylsilyloxy)-2-propyl, 1-(tripropylsilyloxy)-2-propyl, 1-(tributylsilyloxy)-2-propyl, 2-(trimethylsilyloxy)-2-propyl, 2-(dimethylethyl) silyloxy)-2-propyl, 2-(dimethylpropylsilyloxy)-2-propyl, 2-(dimethylisopropylsilyloxy)-2-propyl, 2-(butyldimethylsilyloxy)-2-propyl, 2-( tert-butyldimethylsilyloxy)-2-propyl, 2-(triethylsilyloxy)-2-propyl, 2-(diethylisopropylsilyloxy)-2-propyl, 2-(triisopropylsilyloxy)-2-propyl, A straight chain with 1 to 3 carbon atoms substituted with at least one Z at any position such as 2-(tripropylsilyloxy)-2-propyl or 2-(tributylsilyloxy)-2-propyl Or a branched alkyl group can be mentioned. The number of substitutions for Z may be one or more, and in the case of two or more, the types of Z may be the same or different, and the types of Z are preferably the same. Moreover, the substitution position of Z may be any position.
ロピル、1-フェノキシカルボニルプロピル、1-(フェノキシカルボニル)-2-プロピル、2-(フェノキシカルボニル)-2-プロピル、ベンジルオキシカルボニルメチル、2-ベンジルオキシカルボニルエチル、1-ベンジルオキシカルボニルエチル、3-ベンジルオキシカルボニルプロピル、2-ベンジルオキシカルボニルプロピル、1-ベンジルオキシカルボニルプロピル、1-(ベンジルオキシカルボニル)-2-プロピル、2-(ベンジルオキシカルボニル)-2-プロピル、カルボキシメチル、2-カルボキシエチル、1-カルボキシエチル、3-カルボキシプロピル、2-カルボキシプロピル、1-カルボキシプロピル、1-カルボキシ-2-プロピル、2-カルボキシ-2-プロピル、ヒドロキシメチル、2-ヒドロキシエチル、1-ヒドロキシエチル、3-ヒドロキシプロピル、2-ヒドロキシプロピル、1-ヒドロキシプロピル、1-ヒドロキシ-2-プロピル、2-ヒドロキシ-2-プロピル、トリメチルシリルオキシメチル、ジメチルエチルシリルオキシメチル、ジメチルプロピルシリルオキシメチル、ジメチルイソプロピルシリルオキシメチル、ブチルジメチルシリルオキシメチル、(ターシャリーブチル)ジメチルシリルオキシメチル、トリエチルシリルオキシメチル、ジエチルイソプロピルシリルオキシメチル、トリイソプロピルシリルオキシメチル、トリプロピルシリルオキシメチル、トリブチルシリルオキシメチル、2-(トリメチルシリルオキシ)エチル、2-(ジメチルエチルシリルオキシ)エチル、2-(ジメチルプロピルシリルオキシ)エチル、2-(ジメチルイソプロピルシリルオキシ)エチル、2-(ブチルジメチルシリルオキシ)エチル、2-(ターシャリーブチルジメチルシリルオキシ)エチル、2-(トリエチルシリルオキシ)エチル、2-(ジエチルイソプロピルシリルオキシ)エチル、2-(トリイソプロピルシリルオキシ)エチル、2-(トリプロピルシリルオキシ)エチル、2-(トリブチルシリルオキシ)エチル、1-(トリメチルシリルオキシ)エチル、1-(ジメチルエチルシリルオキシ)エチル、1-(ジメチルプロピルシリルオキシ)エチル、1-(ジメチルイソプロピルシリルオキシ)エチル、1-(ブチルジメチルシリルオキシ)エチル、1-(ターシャリーブチルジメチルシリルオキシ)エチル、1-(トリエチルシリルオキシ)エチル、1-(ジエチルイソプロピルシリルオキシ)エチル、1-(トリイソプロピルシリルオキシ)エチル、1-(トリプロピルシリルオキシ)エチル、1-(トリブチルシリルオキシ)エチル、3-(トリメチルシリルオキシ)プロピル、3-(ジメチルエチルシリルオキシ)プロピル、3-(ジメチルプロピルシリルオキシ)プロピル、3-(ジメチルイソプロピルシリルオキシ)プロピル、3-(ブチルジメチルシリルオキシ)プロピル、3-(ターシャリーブチルジメチルシリルオキシ)プロピル、3-(トリエチルシリルオキシ)プロピル、3-(ジエチルイソプロピルシリルオキシ)プロピル、3-(トリイソプロピルシリルオキシ)プロピル、3-(トリプロピルシリルオキシ)プロピル、3-(トリブチルシリルオキシ)プロピル、2-(トリメチルシリルオキシ)プロピル、2-(ジメチルエチルシリルオキシ)プロピル、2-(ジメチルプロピルシリルオキシ)プロピル、2-(ジメチルイソプロピルシリルオキシ)プロピル、2-(ブチルジメチルシリルオキシ)プロピル、2-(ターシャリーブチルジメチルシリルオキシ)プロピル、2-(トリエチルシリルオキシ)プロピル、2-(ジエチルイソプロピルシリルオキシ)プロピル、2-(トリイソプロピルシリルオキシ)プロピル、2-(トリプロピルシリルオキシ)プロピル、2-(トリブチルシリルオキシ)プロピル、1-(トリメチルシリルオキシ)プロピル、1-(ジメチルエチルシリルオキシ)プロピル、1-(ジメチルプロピルシリルオキシ)プロピル、1-(ジメチルイソプロピルシリルオキシ)プロピル、1-(ブチルジメチルシリルオキシ)プロピル、1-(ターシャリーブチルジメチルシリルオキシ)プロピル、1-(トリエチルシリルオキシ)プロピル、1-(ジエチルイソプロピルシリルオキシ)プロピル、1-(トリイソプロピルシリルオキシ)プロピル、1-(トリプロピルシリルオキシ)プロピル、1-(トリブチルシリルオキシ)プロピル、1-(トリメチルシリルオキシ)-2-プロピル、1-(ジメチルエチルシリルオキシ)-2-プロピル、1-(ジメチルプロピルシリルオキシ)-2-プロピル、1-(ジメチルイソプロピルシリルオキシ)-2-プロピル、1-(ブチルジメチルシリルオキシ)-2-プロピル、1-(ターシャリーブチルジメチルシリルオキシ)-2-プロピル、1-(トリエチルシリルオキシ)-2-プロピル、1-(ジエチルイソプロピルシリルオキシ)-2-プロピル、1-(トリイソプロピルシリルオキシ)-2-プロピル、1-(トリプロピルシリルオキシ)-2-プロピル、1-(トリブチルシリルオキシ)-2-プロピル、2-(トリメチルシリルオキシ)-2-プロピル、2-(ジメチルエチルシリルオキシ)-2-プロピル、2-(ジメチルプロピルシリルオキシ)-2-プロピル、2-(ジメチルイソプロピルシリルオキシ)-2-プロピル、2-(ブチルジメチルシリルオキシ)-2-プロピル、2-(ターシャリーブチルジメチルシリルオキシ)-2-プロピル、2-(トリエチルシリルオキシ)-2-プロピル、2-(ジエチルイソプロピルシリルオキシ)-2-プロピル、2-(トリイソプロピルシリルオキシ)-2-プロピル、2-(トリプロピルシリルオキシ)-2-プロピル又は2-(トリブチルシリルオキシ)-2-プロピル等の任意の位置に少なくとも1個のZで置換された炭素原子数1~3個の直鎖状又は分岐鎖状のアルキル基が挙げられる。Zの置換数は1個又は2個以上であってよく、2個以上の場合、Zの種類は同一でも相異なってもよく、Zの種類は同一が好ましい。また、Zの置換位置はいずれの位置であってもよい。 (C 1 -C 3 )-Alkyl substituted with at least one Z is, for example, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, dicyanomethyl, 2 , 2-dicyanoethyl, methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-Propoxyethyl, 2-isopropoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-iso Propoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, 1-methoxy-2-propyl, 1-ethoxy-2-propyl, 1-propoxy-2-propyl, 1- Isopropoxy-2-propyl, 2-methoxy-2-propyl, 2-ethoxy-2-propyl, 2-propoxy-2-propyl, 2-isopropoxy-2-propyl, dimethoxymethyl, diethoxymethyl, 2,2 -dimethoxyethyl, 2,2-diethoxyethyl, methylthiomethyl, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, 1-methylthioethyl, 1-ethylthioethyl, 1-propylthioethyl, 1-isopropylthioethyl, 2-Methylthioethyl, 2-ethylthioethyl, 2-propylthioethyl, 2-isopropylthioethyl, 1-methylthiopropyl, 1-ethylthiopropyl, 1-propylthiopropyl, 1-isopropylthiopropyl, 2-methylthiopropyl , 2-ethylthiopropyl, 2-propylthiopropyl, 2-isopropylthiopropyl, 3-methylthiopropyl, 3-ethylthiopropyl, 3-propylthiopropyl, 3-isopropylthiopropyl, 1-methylthio-2-propyl, 1-ethylthio-2-propyl, 1-propylthio-2-propyl, 1-isopropylthio-2-propyl, 2-methylthio-2-propyl, 2-ethylthio-2-propyl, 2-propylthio-2-propyl, 2 -isopropylthio-2-propyl, dimethylthiomethyl, diethylthiomethyl, 2,2-dimethylthioethyl, 2,2-diethylthioethyl, cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, 1- Cyclopropylpropyl, 2-cyclopropylpropyl, 3-cyclopropylpropyl, 1-cyclopropyl-2-propyl, 2-cyclopropyl-2-propyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, Trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, per Fluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1-chloro-1-fluoroethyl, 2-chloro-2-fluoro Ethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 2-fluoro-2-propyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3, 3-trifluoropropyl, perfluoropropyl, perfluoroisopropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,1,3,3,3-hexafluoroisopropyl, methylcarbonylmethyl, ethylcarbonyl Methyl, propylcarbonylmethyl, isopropylcarbonylmethyl, butylcarbonylmethyl, isobutylcarbonylmethyl, sec-butylcarbonylmethyl, tert-butylcarbonylmethyl, 2-(methylcarbonyl)ethyl, 2-(ethylcarbonyl)ethyl, 2-(propylcarbonyl) ) Ethyl, 2-(isopropylcarbonyl)ethyl, 2-(butylcarbonyl)ethyl, 2-(isobutylcarbonyl)ethyl, 2-(sec-butyl)ethyl, 2-(tert-butylcarbonyl)ethyl, 1-(methylcarbonyl) ) Ethyl, 1-(ethylcarbonyl)ethyl, 1-(propylcarbonyl)ethyl, 1-(isopropylcarbonyl)ethyl, 1-(butylcarbonyl)ethyl, 1-(isobutylcarbonyl)ethyl, 1-(secondary butylcarbonyl) Ethyl, 1-(tert-butylcarbonyl)ethyl, 3-(methylcarbonyl)propyl, 3-(ethylcarbonyl)propyl, 3-(propylcarbonyl)propyl, 3-(isopropylcarbonyl)propyl, 3-(butylcarbonyl) Propyl, 3-(isobutylcarbonyl)propyl, 3-(sec-butylcarbonyl)propyl, 3-(tert-butylcarbonyl)propyl, 2-(methylcarbonyl)propyl, 2-(ethylcarbonyl)propyl, 2-(propylcarbonyl) ) propyl, 2-(isopropylcarbonyl)propyl, 2-(butylcarbonyl)propyl, 2-(isobutylcarbonyl)propyl, 2-(sec-butylcarbonyl)propyl, 2-(tert-butylcarbonyl)propyl, 1-(methyl) carbonyl)propyl, 1-(ethylcarbonyl)propyl, 1-(propylcarbonyl)propyl, 1-(isopropylcarbonyl)propyl, 1-(butylcarbonyl)propyl, 1-(isobutylcarbonyl)propyl, 1-(secondary butylcarbonyl) ) propyl, 1-(tert-butylcarbonyl)propyl, 1-(methylcarbonyl)-2-propyl, 1-(ethylcarbonyl)-2-propyl, 1-(propylcarbonyl)-2-propyl, 1-(isopropyl) carbonyl)-2-propyl, 1-(butylcarbonyl)-2-propyl, 1-(isobutylcarbonyl)-2-propyl, 1-(sec-butylcarbonyl)-2-propyl, 1-(tert-butylcarbonyl)- 2-propyl, 2-(methylcarbonyl)-2-propyl, 2-(ethylcarbonyl)-2-propyl, 2-(propylcarbonyl)-2-propyl, 2-(isopropylcarbonyl)-2-propyl, 2- (Butylcarbonyl)-2-propyl, 2-(isobutylcarbonyl)-2-propyl, 2-(sec-butylcarbonyl)-2-propyl, 2-(tert-butylcarbonyl)-2-propyl, methoxycarbonylmethyl, ethoxy Carbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, secondary butoxycarbonylmethyl, tert-butoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2- (Propoxycarbonyl)ethyl, 2-(isopropoxycarbonyl)ethyl, 2-(butoxycarbonyl)ethyl, 2-(isobutoxycarbonyl)ethyl, 2-(sec-butoxycarbonyl)ethyl, 2-(tert-butoxycarbonyl)ethyl , 1-(methoxycarbonyl)ethyl, 1-(ethoxycarbonyl)ethyl, 1-(propoxycarbonyl)ethyl, 1-(isopropoxycarbonyl)ethyl, 1-(butoxycarbonyl)ethyl, 1-(isobutoxycarbonyl)ethyl , 1-(sec-butoxycarbonyl)ethyl, 1-(tert-butoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 3-(ethoxycarbonyl)propyl, 3-(propoxycarbonyl)propyl, 3-(isopropoxycarbonyl) ) propyl, 3-(butoxycarbonyl)propyl, 3-(isobutoxycarbonyl)propyl, 3-(sec-butoxycarbonyl)propyl, 3-(tert-butoxycarbonyl)propyl, 2-(methoxycarbonyl)propyl, 2-( ethoxycarbonyl)propyl, 2-(propoxycarbonyl)propyl, 2-(isopropoxycarbonyl)propyl, 2-(butoxycarbonyl)propyl, 2-(isobutoxycarbonyl)propyl, 2-(secondary butoxycarbonyl)propyl, 2- (tert-butoxycarbonyl)propyl, 1-(methoxycarbonyl)propyl, 1-(ethoxycarbonyl)propyl, 1-(propoxycarbonyl)propyl, 1-(isopropoxycarbonyl)propyl, 1-(butoxycarbonyl)propyl, 1 -(isobutoxycarbonyl)propyl, 1-(secondary butoxycarbonyl)propyl, 1-(tert-butoxycarbonyl)propyl, 1-(methoxycarbonyl)-2-propyl, 1-(ethoxycarbonyl)-2-propyl, 1 -(Propoxycarbonyl)-2-propyl, 1-(isopropoxycarbonyl)-2-propyl, 1-(butoxycarbonyl)-2-propyl, 1-(isobutoxycarbonyl)-2-propyl, 1-(secondary butoxy) carbonyl)-2-propyl, 1-(tert-butoxycarbonyl)-2-propyl, 2-(methoxycarbonyl)-2-propyl, 2-(ethoxycarbonyl)-2-propyl, 2-(propoxycarbonyl)-2 -propyl, 2-(isopropoxycarbonyl)-2-propyl, 2-(butoxycarbonyl)-2-propyl, 2-(isobutoxycarbonyl)-2-propyl, 2-(secondary butoxycarbonyl)-2-propyl, 2-(tert-butoxycarbonyl)-2-propyl, cyclopropyloxycarbonylmethyl, cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 2-(cyclopropyloxycarbonyl)ethyl, 2-(cyclobutyl) oxycarbonyl)ethyl, 2-(cyclopentyloxycarbonyl)ethyl, 2-(cyclohexyloxycarbonyl)ethyl, 1-(cyclopropyloxycarbonyl)ethyl, 1-(cyclobutyloxycarbonyl)ethyl, 1-(cyclopentyloxycarbonyl) Ethyl, 1-(cyclohexyloxycarbonyl)ethyl, 3-(cyclopropyloxycarbonyl)propyl, 3-(cyclobutyloxycarbonyl)propyl, 3-(cyclopentyloxycarbonyl)propyl, 3-(cyclohexyloxycarbonyl)propyl, 2 -(cyclopropyloxycarbonyl)propyl, 2-(cyclobutyloxycarbonyl)propyl, 2-(cyclopentyloxycarbonyl)propyl, 2-(cyclohexyloxycarbonyl)propyl, 1-(cyclopropyloxycarbonyl)propyl, 1-( cyclobutyloxycarbonyl)propyl, 1-(cyclopentyloxycarbonyl)propyl, 1-(cyclohexyloxycarbonyl)propyl, 1-methyl-1-(cyclopropyloxycarbonyl)ethyl, 1-methyl-1-(cyclobutyloxycarbonyl) ) Ethyl, 1-methyl-1-(cyclopentyloxycarbonyl)ethyl, 1-methyl-1-(cyclohexyloxycarbonyl)ethyl, 1-(cyclopropyloxycarbonyl)-2-propyl, 1-(cyclobutyloxycarbonyl) -2-propyl, 1-(cyclopentyloxycarbonyl)-2-propyl, 1-(cyclohexyloxycarbonyl)-2-propyl, 2-(cyclopropyloxycarbonyl)-2-propyl, 2-(cyclobutyloxycarbonyl) -2-propyl, 2-(cyclopentyloxycarbonyl)-2-propyl, 2-(cyclohexyloxycarbonyl)-2-propyl, phenoxycarbonylmethyl, 2-phenoxycarbonylethyl, 1-phenoxycarbonylethyl, 3-phenoxycarbonylpropyl , 2-phenoxycarbonylpropyl, 1-phenoxycarbonylpropyl, 1-(phenoxycarbonyl)-2-propyl, 2-(phenoxycarbonyl)-2-propyl, benzyloxycarbonylmethyl, 2-benzyloxycarbonylethyl, 1-benzyl Oxycarbonylethyl, 3-benzyloxycarbonylpropyl, 2-benzyloxycarbonylpropyl, 1-benzyloxycarbonylpropyl, 1-(benzyloxycarbonyl)-2-propyl, 2-(benzyloxycarbonyl)-2-propyl, carboxy Methyl, 2-carboxyethyl, 1-carboxyethyl, 3-carboxypropyl, 2-carboxypropyl, 1-carboxypropyl, 1-carboxy-2-propyl, 2-carboxy-2-propyl, hydroxymethyl, 2-hydroxyethyl , 1-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 1-hydroxypropyl, 1-hydroxy-2-propyl, 2-hydroxy-2-propyl, trimethylsilyloxymethyl, dimethylethylsilyloxymethyl, dimethylpropylsilyl Oxymethyl, dimethylisopropylsilyloxymethyl, butyldimethylsilyloxymethyl, (tert-butyl)dimethylsilyloxymethyl, triethylsilyloxymethyl, diethylisopropylsilyloxymethyl, triisopropylsilyloxymethyl, tripropylsilyloxymethyl, tributylsilyl Oxymethyl, 2-(trimethylsilyloxy)ethyl, 2-(dimethylethylsilyloxy)ethyl, 2-(dimethylpropylsilyloxy)ethyl, 2-(dimethylisopropylsilyloxy)ethyl, 2-(butyldimethylsilyloxy)ethyl , 2-(tert-butyldimethylsilyloxy)ethyl, 2-(triethylsilyloxy)ethyl, 2-(diethylisopropylsilyloxy)ethyl, 2-(triisopropylsilyloxy)ethyl, 2-(tripropylsilyloxy) Ethyl, 2-(tributylsilyloxy)ethyl, 1-(trimethylsilyloxy)ethyl, 1-(dimethylethylsilyloxy)ethyl, 1-(dimethylpropylsilyloxy)ethyl, 1-(dimethylisopropylsilyloxy)ethyl, 1 -(butyldimethylsilyloxy)ethyl, 1-(tert-butyldimethylsilyloxy)ethyl, 1-(triethylsilyloxy)ethyl, 1-(diethylisopropylsilyloxy)ethyl, 1-(triisopropylsilyloxy)ethyl, 1-(Tripropylsilyloxy)ethyl, 1-(tributylsilyloxy)ethyl, 3-(trimethylsilyloxy)propyl, 3-(dimethylethylsilyloxy)propyl, 3-(dimethylpropylsilyloxy)propyl, 3-( dimethylisopropylsilyloxy)propyl, 3-(butyldimethylsilyloxy)propyl, 3-(tert-butyldimethylsilyloxy)propyl, 3-(triethylsilyloxy)propyl, 3-(diethylisopropylsilyloxy)propyl, 3- (triisopropylsilyloxy)propyl, 3-(tripropylsilyloxy)propyl, 3-(tributylsilyloxy)propyl, 2-(trimethylsilyloxy)propyl, 2-(dimethylethylsilyloxy)propyl, 2-(dimethylpropyl) silyloxy)propyl, 2-(dimethylisopropylsilyloxy)propyl, 2-(butyldimethylsilyloxy)propyl, 2-(tert-butyldimethylsilyloxy)propyl, 2-(triethylsilyloxy)propyl, 2-(diethyl Isopropylsilyloxy)propyl, 2-(triisopropylsilyloxy)propyl, 2-(tripropylsilyloxy)propyl, 2-(tributylsilyloxy)propyl, 1-(trimethylsilyloxy)propyl, 1-(dimethylethylsilyloxy) ) propyl, 1-(dimethylpropylsilyloxy)propyl, 1-(dimethylisopropylsilyloxy)propyl, 1-(butyldimethylsilyloxy)propyl, 1-(tert-butyldimethylsilyloxy)propyl, 1-(triethylsilyl) oxy)propyl, 1-(diethylisopropylsilyloxy)propyl, 1-(triisopropylsilyloxy)propyl, 1-(tripropylsilyloxy)propyl, 1-(tributylsilyloxy)propyl, 1-(trimethylsilyloxy)- 2-propyl, 1-(dimethylethylsilyloxy)-2-propyl, 1-(dimethylpropylsilyloxy)-2-propyl, 1-(dimethylisopropylsilyloxy)-2-propyl, 1-(butyldimethylsilyloxy) )-2-propyl, 1-(tert-butyldimethylsilyloxy)-2-propyl, 1-(triethylsilyloxy)-2-propyl, 1-(diethylisopropylsilyloxy)-2-propyl, 1-(triethylsilyloxy)-2-propyl, isopropylsilyloxy)-2-propyl, 1-(tripropylsilyloxy)-2-propyl, 1-(tributylsilyloxy)-2-propyl, 2-(trimethylsilyloxy)-2-propyl, 2-(dimethylethyl) silyloxy)-2-propyl, 2-(dimethylpropylsilyloxy)-2-propyl, 2-(dimethylisopropylsilyloxy)-2-propyl, 2-(butyldimethylsilyloxy)-2-propyl, 2-( tert-butyldimethylsilyloxy)-2-propyl, 2-(triethylsilyloxy)-2-propyl, 2-(diethylisopropylsilyloxy)-2-propyl, 2-(triisopropylsilyloxy)-2-propyl, A straight chain with 1 to 3 carbon atoms substituted with at least one Z at any position such as 2-(tripropylsilyloxy)-2-propyl or 2-(tributylsilyloxy)-2-propyl Or a branched alkyl group can be mentioned. The number of substitutions for Z may be one or more, and in the case of two or more, the types of Z may be the same or different, and the types of Z are preferably the same. Moreover, the substitution position of Z may be any position.
(C1-C3)-アルコキシ又は(C1-C3)-アルコキシ部分は、例えば、メトキシ、エトキシ、ノルマルプロポキシ又はイソプロポキシの炭素原子数1~3個の直鎖状又は分岐鎖状のアルコキシ基が挙げられる。
(C1-C4)-アルコキシ部分は、例えば、メトキシ、エトキシ、ノルマルプロポキシ、イソプロポキシ、ノルマルブトキシ、イソブトキシ、セカンダリ-ブトキシ又はターシャリーブトキシの炭素原子数1~4個の直鎖状又は分岐鎖状のアルコキシ基が挙げられる。 (C 1 -C 3 )-alkoxy or (C 1 -C 3 )-alkoxy moiety is, for example, methoxy, ethoxy, normal propoxy or isopropoxy, straight or branched, having 1 to 3 carbon atoms. Examples include alkoxy groups.
(C 1 -C 4 )-Alkoxy moieties are, for example, methoxy, ethoxy, normal propoxy, isopropoxy, normal butoxy, isobutoxy, secondary butoxy or tertiary butoxy, linear or branched, having 1 to 4 carbon atoms. Examples include chain alkoxy groups.
(C1-C4)-アルコキシ部分は、例えば、メトキシ、エトキシ、ノルマルプロポキシ、イソプロポキシ、ノルマルブトキシ、イソブトキシ、セカンダリ-ブトキシ又はターシャリーブトキシの炭素原子数1~4個の直鎖状又は分岐鎖状のアルコキシ基が挙げられる。 (C 1 -C 3 )-alkoxy or (C 1 -C 3 )-alkoxy moiety is, for example, methoxy, ethoxy, normal propoxy or isopropoxy, straight or branched, having 1 to 3 carbon atoms. Examples include alkoxy groups.
(C 1 -C 4 )-Alkoxy moieties are, for example, methoxy, ethoxy, normal propoxy, isopropoxy, normal butoxy, isobutoxy, secondary butoxy or tertiary butoxy, linear or branched, having 1 to 4 carbon atoms. Examples include chain alkoxy groups.
(C1-C3)-アルキルチオ又は(C1-C3)-アルキルチオ部分は、例えば、メチルチオ、エチルチオ、ノルマルプロピルチオ、又はイソプロピルチオ等の炭素原子数1~3個の直鎖状又は分岐鎖状のアルキルチオ基が挙げられる。(C1)-アルキルチオは、例えば、メチルチオの炭素原子数1個の直鎖状のアルキルチオ基が挙げられる。
(C1-C3)-ハロアルキルチオは、例えばフルオロメチルチオ、ジフルオロメチルチオ、トリフルオロメチルチオ、クロロメチルチオ、ジクロロメチルチオ、トリクロロメチルチオ、クロロジフルオロメチルチオ、ジクロロフルオロメチルチオ、2-フルオロエチルチオ、2,2-ジフルオロエチルチオ、2,2,2-トリフルオロエチルチオ、2-クロロエチルチオ、2,2-ジクロロエチルチオ、2,2,2-トリクロロエチルチオ、パーフルオロエチルチオ、パーフルオロプロピルチオ、パーフルオロイソプロピルチオ、3,3,3-トリフルオロプロピルチオ、2,2,3,3,3-ペンタフルオロプロピルチオ、1,1,1,3,3,3-ヘキサフルオロイソプロピルチオ又は2-フルオロ-2-プロピルチオ等の1~7個の同一のまたは異なるハロゲン原子で置換された、炭素原子数1~3個の直鎖状又は分岐鎖状のアルキルチオ基が挙げられる。(C1)-ハロアルキルチオは、例えばフルオロメチルチオ、ジフルオロメチルチオ、トリフルオロメチルチオ、クロロメチルチオ、ジクロロメチルチオ、トリクロロメチルチオ、クロロジフルオロメチルチオ、ジクロロフルオロメチルチオ等の1~3個の同一のまたは異なるハロゲン原子で置換された、炭素原子数1個の直鎖状のアルキルチオ基が挙げられる。 The (C 1 -C 3 )-alkylthio or (C 1 -C 3 )-alkylthio moiety is, for example, a linear or branched chain having 1 to 3 carbon atoms, such as methylthio, ethylthio, n-propylthio, or isopropylthio. Examples include chain alkylthio groups. (C 1 )-Alkylthio includes, for example, a linear alkylthio group having one carbon atom, such as methylthio.
(C 1 -C 3 )-Haloalkylthio is, for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloromethylthio, dichloromethylthio, trichloromethylthio, chlorodifluoromethylthio, dichlorofluoromethylthio, 2-fluoroethylthio, 2,2- Difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloroethylthio, 2,2-dichloroethylthio, 2,2,2-trichloroethylthio, perfluoroethylthio, perfluoropropylthio, perfluoroethylthio Fluoroisopropylthio, 3,3,3-trifluoropropylthio, 2,2,3,3,3-pentafluoropropylthio, 1,1,1,3,3,3-hexafluoroisopropylthio or 2-fluoro Examples include straight-chain or branched alkylthio groups having 1 to 3 carbon atoms and substituted with 1 to 7 identical or different halogen atoms, such as -2-propylthio. (C 1 )-Haloalkylthio means 1 to 3 identical or different halogen atoms, such as fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloromethylthio, dichloromethylthio, trichloromethylthio, chlorodifluoromethylthio, dichlorofluoromethylthio, etc. Examples include substituted linear alkylthio groups having one carbon atom.
(C1-C3)-ハロアルキルチオは、例えばフルオロメチルチオ、ジフルオロメチルチオ、トリフルオロメチルチオ、クロロメチルチオ、ジクロロメチルチオ、トリクロロメチルチオ、クロロジフルオロメチルチオ、ジクロロフルオロメチルチオ、2-フルオロエチルチオ、2,2-ジフルオロエチルチオ、2,2,2-トリフルオロエチルチオ、2-クロロエチルチオ、2,2-ジクロロエチルチオ、2,2,2-トリクロロエチルチオ、パーフルオロエチルチオ、パーフルオロプロピルチオ、パーフルオロイソプロピルチオ、3,3,3-トリフルオロプロピルチオ、2,2,3,3,3-ペンタフルオロプロピルチオ、1,1,1,3,3,3-ヘキサフルオロイソプロピルチオ又は2-フルオロ-2-プロピルチオ等の1~7個の同一のまたは異なるハロゲン原子で置換された、炭素原子数1~3個の直鎖状又は分岐鎖状のアルキルチオ基が挙げられる。(C1)-ハロアルキルチオは、例えばフルオロメチルチオ、ジフルオロメチルチオ、トリフルオロメチルチオ、クロロメチルチオ、ジクロロメチルチオ、トリクロロメチルチオ、クロロジフルオロメチルチオ、ジクロロフルオロメチルチオ等の1~3個の同一のまたは異なるハロゲン原子で置換された、炭素原子数1個の直鎖状のアルキルチオ基が挙げられる。 The (C 1 -C 3 )-alkylthio or (C 1 -C 3 )-alkylthio moiety is, for example, a linear or branched chain having 1 to 3 carbon atoms, such as methylthio, ethylthio, n-propylthio, or isopropylthio. Examples include chain alkylthio groups. (C 1 )-Alkylthio includes, for example, a linear alkylthio group having one carbon atom, such as methylthio.
(C 1 -C 3 )-Haloalkylthio is, for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloromethylthio, dichloromethylthio, trichloromethylthio, chlorodifluoromethylthio, dichlorofluoromethylthio, 2-fluoroethylthio, 2,2- Difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloroethylthio, 2,2-dichloroethylthio, 2,2,2-trichloroethylthio, perfluoroethylthio, perfluoropropylthio, perfluoroethylthio Fluoroisopropylthio, 3,3,3-trifluoropropylthio, 2,2,3,3,3-pentafluoropropylthio, 1,1,1,3,3,3-hexafluoroisopropylthio or 2-fluoro Examples include straight-chain or branched alkylthio groups having 1 to 3 carbon atoms and substituted with 1 to 7 identical or different halogen atoms, such as -2-propylthio. (C 1 )-Haloalkylthio means 1 to 3 identical or different halogen atoms, such as fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloromethylthio, dichloromethylthio, trichloromethylthio, chlorodifluoromethylthio, dichlorofluoromethylthio, etc. Examples include substituted linear alkylthio groups having one carbon atom.
R2とR3が一緒になって、R2とR3に結合した窒素原子と3~5員環を形成し得るが、この環は飽和でも不飽和でもよい。例えば、飽和環としてはアジリジン、アゼチジン又はピロリジンが挙げられ、不飽和としてはピロール又はジヒドロピロールが挙げられる。
R 2 and R 3 together may form a 3- to 5-membered ring with the nitrogen atom bonded to R 2 and R 3 , which ring may be saturated or unsaturated. For example, saturated rings include aziridine, azetidine or pyrrolidine, and unsaturated rings include pyrrole or dihydropyrrole.
「nは1から5の整数である」とは、nが1、2、3、4又は5であることを意味する。また、化合物(I)、化合物(IA)又は化合物(IB)の特定の態様において、nは1から2、1から3、1から4、2から3、2から4、2から5、3から4、3から5又は4から5の整数の場合もある。
"n is an integer from 1 to 5" means that n is 1, 2, 3, 4, or 5. Further, in specific embodiments of compound (I), compound (IA) or compound (IB), n is 1 to 2, 1 to 3, 1 to 4, 2 to 3, 2 to 4, 2 to 5, 3 to It may also be an integer from 4, 3 to 5, or 4 to 5.
化合物(I)、化合物(IA)又は化合物(IB)の塩としては、農業上許容されるものであればあらゆるものが含まれるが、例えば、アルカリ金属塩(例えば、ナトリウム塩、カリウム塩など)、アルカリ土類金属塩(例えば、マグネシウム塩、カルシウム塩など)、アミン塩(ジメチルアミン塩、トリエチルアミン塩など)、無機酸塩(例えば、塩酸塩、過塩素酸塩、硫酸塩、硝酸塩など)又は有機酸塩(例えば酢酸塩、メタンスルホン酸塩、パラトルエンスルホン酸塩、シュウ酸塩など)などが挙げられる。
The salts of compound (I), compound (IA) or compound (IB) include all agriculturally acceptable salts, including alkali metal salts (e.g., sodium salts, potassium salts, etc.) , alkaline earth metal salts (e.g. magnesium salts, calcium salts, etc.), amine salts (dimethylamine salts, triethylamine salts, etc.), inorganic acid salts (e.g. hydrochlorides, perchlorates, sulfates, nitrates, etc.) or Examples include organic acid salts (eg, acetate, methanesulfonate, paratoluenesulfonate, oxalate, etc.).
化合物(I)、化合物(IA)及び化合物(IB)は、各種異性体、例えば光学異性体、幾何異性体などが存在するが、本発明には各異性体及び異性体混合物の双方が含まれることがある。なお、化合物(I)、化合物(IA)及び化合物(IB)には、当該技術分野における技術常識の範囲内において、前記したもの以外の各種異性体も含まれる。さらに、当該技術分野における技術常識及び一般的な実験手法を用いて、各種異性体を作り分けることができる。
Compound (I), compound (IA) and compound (IB) exist in various isomers, such as optical isomers and geometric isomers, and the present invention includes both isomers and mixtures of isomers. Sometimes. Note that Compound (I), Compound (IA), and Compound (IB) also include various isomers other than those described above within the scope of common technical knowledge in the technical field. Furthermore, various isomers can be separately produced using common technical knowledge and general experimental methods in the relevant technical field.
また、異性体の種類によっては、記載した構造式と異なる化学構造となる場合があるが、当業者であればそれらが異性体の関係にあることが十分認識できる為、本発明の範囲内であることは明らかである。
Furthermore, depending on the type of isomer, it may have a chemical structure different from the described structural formula, but a person skilled in the art will be able to fully recognize that they are in an isomer relationship, and therefore within the scope of the present invention. It is clear that there is.
次に化合物(I)の製造方法について説明する。化合物(I)には化合物(IA)及び化合物(IB)が包含され、したがって以下の説明には、化合物(IA)及び化合物(IB)の製造方法も含まれる。
化合物(I)は、以下に示す製造方法1(反応A~反応L)、及び通常の塩の製造方法に従って製造することができるが、当該化合物を得る方法は、これらの方法に限定されるものではない。例えば、本発明の化合物(I)は、フェニル基上の置換基に、本分野において周知の種々の置換基変換反応(例えば、アルキル化反応、ハロアルキル化反応、鈴木カップリング反応などのクロスカップリング反応、ザンドマイヤー型反応、ハロゲン化反応、酸化反応、還元反応等)を、適用することによって製造することも可能である。また、必要に応じて、本発明化合物の製造において、本分野において通常使用される保護及び脱保護反応を適用してもよい。反応を実施するにあたり、必要な場合は窒素やアルゴンなどの不活性ガス雰囲気下で実施してもよく、塩の試薬を用いてもよい。 Next, a method for producing compound (I) will be explained. Compound (I) includes Compound (IA) and Compound (IB), and therefore, the following description also includes methods for producing Compound (IA) and Compound (IB).
Compound (I) can be produced according to Production Method 1 (Reaction A to Reaction L) shown below and the usual salt production method, but the method for obtaining the compound is limited to these methods. isn't it. For example, the compound (I) of the present invention can be subjected to various substituent conversion reactions well known in the art (e.g., alkylation reaction, haloalkylation reaction, cross-coupling reaction such as Suzuki coupling reaction) to the substituent on the phenyl group. reaction, Sandmeyer type reaction, halogenation reaction, oxidation reaction, reduction reaction, etc.). Furthermore, if necessary, protection and deprotection reactions commonly used in this field may be applied in the production of the compounds of the present invention. When carrying out the reaction, if necessary, the reaction may be carried out under an inert gas atmosphere such as nitrogen or argon, or a salt reagent may be used.
化合物(I)は、以下に示す製造方法1(反応A~反応L)、及び通常の塩の製造方法に従って製造することができるが、当該化合物を得る方法は、これらの方法に限定されるものではない。例えば、本発明の化合物(I)は、フェニル基上の置換基に、本分野において周知の種々の置換基変換反応(例えば、アルキル化反応、ハロアルキル化反応、鈴木カップリング反応などのクロスカップリング反応、ザンドマイヤー型反応、ハロゲン化反応、酸化反応、還元反応等)を、適用することによって製造することも可能である。また、必要に応じて、本発明化合物の製造において、本分野において通常使用される保護及び脱保護反応を適用してもよい。反応を実施するにあたり、必要な場合は窒素やアルゴンなどの不活性ガス雰囲気下で実施してもよく、塩の試薬を用いてもよい。 Next, a method for producing compound (I) will be explained. Compound (I) includes Compound (IA) and Compound (IB), and therefore, the following description also includes methods for producing Compound (IA) and Compound (IB).
Compound (I) can be produced according to Production Method 1 (Reaction A to Reaction L) shown below and the usual salt production method, but the method for obtaining the compound is limited to these methods. isn't it. For example, the compound (I) of the present invention can be subjected to various substituent conversion reactions well known in the art (e.g., alkylation reaction, haloalkylation reaction, cross-coupling reaction such as Suzuki coupling reaction) to the substituent on the phenyl group. reaction, Sandmeyer type reaction, halogenation reaction, oxidation reaction, reduction reaction, etc.). Furthermore, if necessary, protection and deprotection reactions commonly used in this field may be applied in the production of the compounds of the present invention. When carrying out the reaction, if necessary, the reaction may be carried out under an inert gas atmosphere such as nitrogen or argon, or a salt reagent may be used.
製造方法1
[反応A]
反応Aは、脱保護反応であり、式(XX-a)の化合物よりBoc基を除くことにより、式(I)の化合物を得る方法である。ここで、Boc基は、tert-ブトキシカルボニル基である。 Manufacturing method 1
[Reaction A]
Reaction A is a deprotection reaction, and is a method for obtaining the compound of formula (I) by removing the Boc group from the compound of formula (XX-a). Here, the Boc group is a tert-butoxycarbonyl group.
[反応A]
反応Aは、脱保護反応であり、式(XX-a)の化合物よりBoc基を除くことにより、式(I)の化合物を得る方法である。ここで、Boc基は、tert-ブトキシカルボニル基である。 Manufacturing method 1
[Reaction A]
Reaction A is a deprotection reaction, and is a method for obtaining the compound of formula (I) by removing the Boc group from the compound of formula (XX-a). Here, the Boc group is a tert-butoxycarbonyl group.
式中の記号は前述の通りである。
The symbols in the formula are as described above.
反応Aは、Boc基を除くために用いられる公知の条件、例えば、Greene’s PROTECTIVE GROUPS in ORGANIC SYNTHESIS(John Wiley and Sons、2007年、Peter G.M.Wuts、Theodora W.Greene)に記載の方法によって行うことができる。より具体的には、例えば、溶媒存在下、トリフルオロ酢酸や塩化水素などの酸と反応させる、あるいは溶媒及び2,6-ルチジンのような塩基存在下、トリメチルシリルトリフラートと反応させることによって行うことができる。
Reaction A is performed using known conditions used to remove the Boc group, such as Greene's PROTECTIVE GROUPS in ORGANIC SYNTHESIS (John Wiley and Sons, 2007, Peter G.M. .Wuts, Theodora W. Greene). This can be done by any method. More specifically, it can be carried out, for example, by reacting with an acid such as trifluoroacetic acid or hydrogen chloride in the presence of a solvent, or by reacting with trimethylsilyl triflate in the presence of a solvent and a base such as 2,6-lutidine. can.
[反応B]及び[反応C]
反応Bは、式(II)の化合物と式(III)の化合物を反応させ式(XX-b)の化合物を得る方法である。反応Cは、式(II-a)の化合物と式(III)の化合物を反応させ式(XX-b)の化合物を得る方法である。 [Reaction B] and [Reaction C]
Reaction B is a method in which a compound of formula (II) and a compound of formula (III) are reacted to obtain a compound of formula (XX-b). Reaction C is a method in which a compound of formula (II-a) and a compound of formula (III) are reacted to obtain a compound of formula (XX-b).
反応Bは、式(II)の化合物と式(III)の化合物を反応させ式(XX-b)の化合物を得る方法である。反応Cは、式(II-a)の化合物と式(III)の化合物を反応させ式(XX-b)の化合物を得る方法である。 [Reaction B] and [Reaction C]
Reaction B is a method in which a compound of formula (II) and a compound of formula (III) are reacted to obtain a compound of formula (XX-b). Reaction C is a method in which a compound of formula (II-a) and a compound of formula (III) are reacted to obtain a compound of formula (XX-b).
式中、AはNH2又はNH(Boc)であり、R2aはH、(C1-C3)-アルキル又はBocであり、R2aが(C1-C3)-アルキルの場合、R2aとR3は一緒になって、R2aとR3に結合した窒素原子と3~5員環(例えばアジリジン、アゼチジン、ピロリジン、ジヒドロピロール又はピロール)を形成してもよい。Lは脱離基であり、例えば、ハロゲン、アルコキシ、アリールオキシ、アルキルカルボニルオキシ、アリールカルボニルオキシなどが挙げられる。その他の記号は前述の通りである。
In the formula, A is NH 2 or NH(Boc), R 2a is H, (C 1 -C 3 )-alkyl or Boc, and when R 2a is (C 1 -C 3 )-alkyl, R 2a and R 3 may together form a 3- to 5-membered ring (eg aziridine, azetidine, pyrrolidine, dihydropyrrole or pyrrole) with the nitrogen atom attached to R 2a and R 3 . L is a leaving group, and examples thereof include halogen, alkoxy, aryloxy, alkylcarbonyloxy, and arylcarbonyloxy. Other symbols are as described above.
反応Bは、通常、脱水縮合剤及び溶媒の存在下、必要に応じて塩基を加えて行うことができる。式(III)の化合物は、式(II)の化合物1当量に対して、0.5~3当量、望ましくは0.8~1.5当量使用できる(当量はモル当量であり、以下も同様である)。
Reaction B can usually be carried out in the presence of a dehydration condensation agent and a solvent, with the addition of a base if necessary. The compound of formula (III) can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per 1 equivalent of the compound of formula (II) (equivalents are molar equivalents, and the same applies below) ).
反応Bにおける脱水縮合剤としては、N,N’-ジシクロヘキシルカルボジイミド(DCC)、1-[3-(ジメチルアミノ)プロピル]-3-エチルカルボジイミド(EDC)又はその塩酸塩のようなカルボジイミド系縮合剤;1,1’-カルボニルジイミダゾール(CDI)のようなイミダゾール系縮合剤;4-(4,6-ジメトキシ-1,3,5-トリアジン-2-イル)-4-メチルモルホリニウムクロリド(DMT-MM)のようなトリアジン系縮合剤;1H-ベンゾトリアゾール-1-イルオキシトリピロリジノホスホニウムヘキサフルオロホスファート(PyBOP)のようなホスホニウム系縮合剤;1-[ビス(ジメチルアミノ)メチレン]-1H-1,2,3-トリアゾロ[4,5-b]ピリジニウム 3-オキシドヘキサフルオロホスファート(HATU)のようなウロニウム系縮合剤;2-メチル-6-ニトロ安息香酸無水物(MNBA)のような酸無水物;2-クロロ-1-メチルピリジニウム p-トルエンスルホナートのような2-ハロピリジニウム塩;プロピルホスホン酸無水物(環状トリマー)(T3P);ジフェニルリン酸アジド(DPPA);などが挙げられるが、これらに限定されるものではない。必要に応じて1-ヒドロキシベンゾトリアゾール(HOBt)などの脱水縮合剤とともに使用される一般的な添加剤を添加してもよい。脱水縮合剤は、式(II)の化合物1当量に対して、0.5~5当量、望ましくは1~2当量使用でき、添加剤は式(II)の化合物1当量に対して、0.2~5当量、望ましくは1~2当量使用できる。
As the dehydration condensing agent in reaction B, a carbodiimide condensing agent such as N,N'-dicyclohexylcarbodiimide (DCC), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDC), or its hydrochloride; ; Imidazole condensing agent such as 1,1'-carbonyldiimidazole (CDI); 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride ( Triazine condensing agents such as DMT-MM); Phosphonium condensing agents such as 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP); 1-[bis(dimethylamino)methylene] -1H-1,2,3-triazolo[4,5-b]pyridinium uronium-based condensing agents such as 3-oxidohexafluorophosphate (HATU); 2-methyl-6-nitrobenzoic anhydride (MNBA) acid anhydrides such as; 2-halopyridinium salts such as 2-chloro-1-methylpyridinium p-toluenesulfonate; propylphosphonic anhydride (cyclic trimer) (T3P); diphenylphosphoric azide (DPPA); Examples include, but are not limited to, the following. If necessary, common additives used together with dehydration condensation agents such as 1-hydroxybenzotriazole (HOBt) may be added. The dehydration condensation agent can be used in an amount of 0.5 to 5 equivalents, preferably 1 to 2 equivalents, per equivalent of the compound of formula (II), and the additive can be used in an amount of 0.5 to 5 equivalents, preferably 1 to 2 equivalents, per equivalent of the compound of formula (II). 2 to 5 equivalents, preferably 1 to 2 equivalents can be used.
反応Bにおける塩基は、例えば、炭酸ナトリウム、炭酸カリウムのような炭酸塩;炭酸水素ナトリウム、炭酸水素カリウムのような炭酸水素塩;水酸化ナトリウム、水酸化カリウムのような金属水酸化物;水素化ナトリウム、水素化カリウムのような金属水素化物;トリエチルアミン、N,N-ジイソプロピルエチルアミンのようなアミン類;ピリジン、4-ジメチルアミノピリジン、2,6-ルチジンのようなピリジン類;酢酸ナトリウム、酢酸カリウムなどのアルカリ金属カルボン酸塩;などから1種又は2種以上を適宜選択、混合して使用することができる。塩基は、式(II)の化合物1当量に対して、0.5~10当量、望ましくは1~5当量使用できる。
反応Bにおける溶媒は、反応に不活性な溶媒であればいずれのものでもよく、例えば、ベンゼン、トルエン、キシレン、クロロベンゼンのような芳香族炭化水素類;四塩化炭素、塩化メチル、クロロホルム、ジクロロメタン、ジクロロエタン、トリクロロエタン、ヘキサン、シクロヘキサンのような脂肪族炭化水素類;ジオキサン、テトラヒドロフラン、ジエチルエーテル、ジメトキシエタンのようなエーテル類;酢酸メチル、酢酸エチルのようなエステル類;ジメチルスルホキシド、スルホラン、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、N-メチルピロリドン、ピリジン、アセトニトリル、プロピオニトリルのような非プロトン性極性溶媒;アセトン、メチルエチルケトンのようなケトン類;メタノール、エタノールのようなプロトン性極性溶媒;水;などから1種又は2種以上を適宜選択できる。 The base in reaction B can be, for example, a carbonate such as sodium carbonate or potassium carbonate; a bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate; a metal hydroxide such as sodium hydroxide or potassium hydroxide; Metal hydrides such as sodium and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; sodium acetate and potassium acetate Alkali metal carboxylates such as; and the like, one type or two or more types can be appropriately selected and used in combination. The base can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per 1 equivalent of the compound of formula (II).
The solvent in reaction B may be any solvent as long as it is inert to the reaction; for example, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, Aliphatic hydrocarbons such as dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; dimethyl sulfoxide, sulfolane, N,N - Aprotic polar solvents such as dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, propionitrile; ketones such as acetone, methyl ethyl ketone; protic polar solvents such as methanol, ethanol One or more types can be appropriately selected from solvents; water; and the like.
反応Bにおける溶媒は、反応に不活性な溶媒であればいずれのものでもよく、例えば、ベンゼン、トルエン、キシレン、クロロベンゼンのような芳香族炭化水素類;四塩化炭素、塩化メチル、クロロホルム、ジクロロメタン、ジクロロエタン、トリクロロエタン、ヘキサン、シクロヘキサンのような脂肪族炭化水素類;ジオキサン、テトラヒドロフラン、ジエチルエーテル、ジメトキシエタンのようなエーテル類;酢酸メチル、酢酸エチルのようなエステル類;ジメチルスルホキシド、スルホラン、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、N-メチルピロリドン、ピリジン、アセトニトリル、プロピオニトリルのような非プロトン性極性溶媒;アセトン、メチルエチルケトンのようなケトン類;メタノール、エタノールのようなプロトン性極性溶媒;水;などから1種又は2種以上を適宜選択できる。 The base in reaction B can be, for example, a carbonate such as sodium carbonate or potassium carbonate; a bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate; a metal hydroxide such as sodium hydroxide or potassium hydroxide; Metal hydrides such as sodium and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; sodium acetate and potassium acetate Alkali metal carboxylates such as; and the like, one type or two or more types can be appropriately selected and used in combination. The base can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per 1 equivalent of the compound of formula (II).
The solvent in reaction B may be any solvent as long as it is inert to the reaction; for example, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, Aliphatic hydrocarbons such as dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; dimethyl sulfoxide, sulfolane, N,N - Aprotic polar solvents such as dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, propionitrile; ketones such as acetone, methyl ethyl ketone; protic polar solvents such as methanol, ethanol One or more types can be appropriately selected from solvents; water; and the like.
反応Bの反応温度は、通常-20℃~150℃程度、望ましくは0℃~100℃程度であり、反応時間は、通常0.5~48時間程度、望ましくは1~24時間程度である。
The reaction temperature for reaction B is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.
反応Cは、溶媒の存在下、必要に応じて塩基を加えて行うことができる。式(III)の化合物は、式(II-a)の化合物1当量に対して、0.5~3当量、望ましくは0.8~1.5当量使用できる。
Reaction C can be carried out in the presence of a solvent and optionally with the addition of a base. The compound of formula (III) can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of formula (II-a).
反応Cにおける塩基は、例えば、炭酸ナトリウム、炭酸カリウムのような炭酸塩;炭酸水素ナトリウム、炭酸水素カリウムのような炭酸水素塩;水酸化ナトリウム、水酸化カリウムのような金属水酸化物;水素化ナトリウム、水素化カリウムのような金属水素化物;トリエチルアミン、N,N-ジイソプロピルエチルアミンのようなアミン類;ピリジン、4-ジメチルアミノピリジン、2,6-ルチジンのようなピリジン類;酢酸ナトリウム、酢酸カリウムなどのアルカリ金属カルボン酸塩;などから1種又は2種以上を適宜選択、混合して使用することができる。塩基は、式(II-a)の化合物1当量に対して、0.1~10当量、望ましくは0.5~5当量使用できる。
反応Cにおける溶媒は、反応に不活性な溶媒であればいずれのものでもよく、例えば、ベンゼン、トルエン、キシレン、クロロベンゼンのような芳香族炭化水素類;四塩化炭素、塩化メチル、クロロホルム、ジクロロメタン、ジクロロエタン、トリクロロエタン、ヘキサン、シクロヘキサンのような脂肪族炭化水素類;ジオキサン、テトラヒドロフラン、ジエチルエーテル、ジメトキシエタンのようなエーテル類;酢酸メチル、酢酸エチルのようなエステル類;ジメチルスルホキシド、スルホラン、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、N-メチルピロリドン、ピリジン、アセトニトリル、プロピオニトリルのような非プロトン性極性溶媒;アセトン、メチルエチルケトンのようなケトン類;メタノール、エタノールのようなプロトン性極性溶媒;水;などから1種又は2種以上を適宜選択できる。 The base in reaction C can be, for example, a carbonate such as sodium carbonate or potassium carbonate; a bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate; a metal hydroxide such as sodium hydroxide or potassium hydroxide; Metal hydrides such as sodium and potassium hydride; Amines such as triethylamine and N,N-diisopropylethylamine; Pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; Sodium acetate and potassium acetate Alkali metal carboxylates such as; and the like, one type or two or more types can be appropriately selected and used in combination. The base can be used in an amount of 0.1 to 10 equivalents, preferably 0.5 to 5 equivalents, per 1 equivalent of the compound of formula (II-a).
The solvent in reaction C may be any solvent as long as it is inert to the reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, Aliphatic hydrocarbons such as dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; dimethyl sulfoxide, sulfolane, N,N - Aprotic polar solvents such as dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, propionitrile; ketones such as acetone, methyl ethyl ketone; protic polar solvents such as methanol, ethanol One or more types can be appropriately selected from solvents; water; and the like.
反応Cにおける溶媒は、反応に不活性な溶媒であればいずれのものでもよく、例えば、ベンゼン、トルエン、キシレン、クロロベンゼンのような芳香族炭化水素類;四塩化炭素、塩化メチル、クロロホルム、ジクロロメタン、ジクロロエタン、トリクロロエタン、ヘキサン、シクロヘキサンのような脂肪族炭化水素類;ジオキサン、テトラヒドロフラン、ジエチルエーテル、ジメトキシエタンのようなエーテル類;酢酸メチル、酢酸エチルのようなエステル類;ジメチルスルホキシド、スルホラン、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、N-メチルピロリドン、ピリジン、アセトニトリル、プロピオニトリルのような非プロトン性極性溶媒;アセトン、メチルエチルケトンのようなケトン類;メタノール、エタノールのようなプロトン性極性溶媒;水;などから1種又は2種以上を適宜選択できる。 The base in reaction C can be, for example, a carbonate such as sodium carbonate or potassium carbonate; a bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate; a metal hydroxide such as sodium hydroxide or potassium hydroxide; Metal hydrides such as sodium and potassium hydride; Amines such as triethylamine and N,N-diisopropylethylamine; Pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; Sodium acetate and potassium acetate Alkali metal carboxylates such as; and the like, one type or two or more types can be appropriately selected and used in combination. The base can be used in an amount of 0.1 to 10 equivalents, preferably 0.5 to 5 equivalents, per 1 equivalent of the compound of formula (II-a).
The solvent in reaction C may be any solvent as long as it is inert to the reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, Aliphatic hydrocarbons such as dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; dimethyl sulfoxide, sulfolane, N,N - Aprotic polar solvents such as dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, propionitrile; ketones such as acetone, methyl ethyl ketone; protic polar solvents such as methanol, ethanol One or more types can be appropriately selected from solvents; water; and the like.
反応Cの反応温度は、通常-20℃~150℃程度、望ましくは0℃~100℃程度であり、反応時間は、通常0.5~48時間程度、望ましくは1~24時間程度である。
The reaction temperature for reaction C is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.
反応Bで使用される式(II)の化合物は、下記反応1-1、反応1-2又は公知の方法に準じて製造することができ、又は市販品を使用しても良い。式(III)の化合物は、下記反応2-2、反応2-4又は反応2-6に従って製造することができる。
反応Cで使用される式(II-a)の化合物は、式(II)の化合物より公知の方法に準じて製造することができ、又は市販品を使用しても良い。 The compound of formula (II) used in reaction B can be produced according to the following reaction 1-1, reaction 1-2 or a known method, or a commercially available product may be used. The compound of formula (III) can be produced according to Reaction 2-2, Reaction 2-4 or Reaction 2-6 below.
The compound of formula (II-a) used in reaction C can be produced from the compound of formula (II) according to known methods, or a commercially available product may be used.
反応Cで使用される式(II-a)の化合物は、式(II)の化合物より公知の方法に準じて製造することができ、又は市販品を使用しても良い。 The compound of formula (II) used in reaction B can be produced according to the following reaction 1-1, reaction 1-2 or a known method, or a commercially available product may be used. The compound of formula (III) can be produced according to Reaction 2-2, Reaction 2-4 or Reaction 2-6 below.
The compound of formula (II-a) used in reaction C can be produced from the compound of formula (II) according to known methods, or a commercially available product may be used.
[反応D]
反応Dは、式(XX-c)の化合物からBoc基を除くことにより、式(XX-d)若しくは式(XX-e)の化合物を経て式(I-a)の化合物を得る方法である。反応Dは、式(XX-d)、式(XX-e)の化合物又はこれらの混合物を単離せずに、式(XX-c)の化合物から式(I-a)の化合物を直接得ることもできる。 [Reaction D]
Reaction D is a method of obtaining a compound of formula (I-a) via a compound of formula (XX-d) or formula (XX-e) by removing the Boc group from a compound of formula (XX-c). . Reaction D is to directly obtain a compound of formula (I-a) from a compound of formula (XX-c) without isolating the compound of formula (XX-d), formula (XX-e) or a mixture thereof. You can also do it.
反応Dは、式(XX-c)の化合物からBoc基を除くことにより、式(XX-d)若しくは式(XX-e)の化合物を経て式(I-a)の化合物を得る方法である。反応Dは、式(XX-d)、式(XX-e)の化合物又はこれらの混合物を単離せずに、式(XX-c)の化合物から式(I-a)の化合物を直接得ることもできる。 [Reaction D]
Reaction D is a method of obtaining a compound of formula (I-a) via a compound of formula (XX-d) or formula (XX-e) by removing the Boc group from a compound of formula (XX-c). . Reaction D is to directly obtain a compound of formula (I-a) from a compound of formula (XX-c) without isolating the compound of formula (XX-d), formula (XX-e) or a mixture thereof. You can also do it.
式中の記号は前述の通りである。
反応Dは、上記反応Aに準じて行うことができる。 The symbols in the formula are as described above.
Reaction D can be carried out according to reaction A above.
反応Dは、上記反応Aに準じて行うことができる。 The symbols in the formula are as described above.
Reaction D can be carried out according to reaction A above.
[反応E]及び[反応F]
反応Eは、式(XX-f)の化合物を式(IV-a)の化合物又は式(IV-b)の化合物と反応させ式(XX-g)の化合物を得る方法である。反応Fは、式(XX-g)の化合物を還元し式(XX-h)の化合物を得る方法である。式(XX-g)の化合物を単離せずに、反応Eと反応Fは連続して行うこともできる。 [Reaction E] and [Reaction F]
Reaction E is a method in which a compound of formula (XX-f) is reacted with a compound of formula (IV-a) or a compound of formula (IV-b) to obtain a compound of formula (XX-g). Reaction F is a method of reducing a compound of formula (XX-g) to obtain a compound of formula (XX-h). Reactions E and F can also be carried out consecutively without isolating the compound of formula (XX-g).
反応Eは、式(XX-f)の化合物を式(IV-a)の化合物又は式(IV-b)の化合物と反応させ式(XX-g)の化合物を得る方法である。反応Fは、式(XX-g)の化合物を還元し式(XX-h)の化合物を得る方法である。式(XX-g)の化合物を単離せずに、反応Eと反応Fは連続して行うこともできる。 [Reaction E] and [Reaction F]
Reaction E is a method in which a compound of formula (XX-f) is reacted with a compound of formula (IV-a) or a compound of formula (IV-b) to obtain a compound of formula (XX-g). Reaction F is a method of reducing a compound of formula (XX-g) to obtain a compound of formula (XX-h). Reactions E and F can also be carried out consecutively without isolating the compound of formula (XX-g).
式中、R3aはH、(C1-C2)-アルキル、(C2-C4)-アルキニル、(C2-C3)-アルケニル、(C2-C3)-ハロアルケニル、又はZで置換された(C1-C2)-アルキルであり、R3bはH又はメチルである。R3aとR3bは一緒になって3~4員の炭素環(例えばシクロプロピル又はシクロブチル)を形成してもよく、Y1はアルキルであり、Y2はH又はアルキルであり、その他の記号は前述の通りである。
In the formula, R 3a is H, (C 1 -C 2 )-alkyl, (C 2 -C 4 )-alkynyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, or (C 1 -C 2 )-alkyl substituted with Z, and R 3b is H or methyl. R 3a and R 3b may be taken together to form a 3-4 membered carbocycle (e.g. cyclopropyl or cyclobutyl), Y 1 is alkyl, Y 2 is H or alkyl, and other symbols is as described above.
反応Eは、必要に応じて酸、塩基又は脱水剤を添加して行うことができ、溶媒を使用してもよい。式(IV-a)又は式(IV-b)の化合物は、式(XX-f)の化合物1当量に対して、通常1~5当量、反応に問題がなければ過剰に用いてもよい。
Reaction E can be carried out by adding an acid, a base, or a dehydrating agent as necessary, and a solvent may be used. The compound of formula (IV-a) or formula (IV-b) is usually used in an amount of 1 to 5 equivalents per equivalent of the compound of formula (XX-f), and may be used in excess if there is no problem with the reaction.
反応Eにおける酸は、無機酸、有機酸のいずれでもよく、無機酸としては塩酸、硫酸など、有機酸としては酢酸、メタンスルホン酸、パラトルエンスルホン酸などが挙げられる。
反応Eにおける塩基は、例えば、ナトリウムメトキシド、ナトリウムエトキシド、カリウムtert-ブトキシドのようなアルカリ金属アルコキシド;炭酸ナトリウム、炭酸カリウムのような炭酸塩;炭酸水素ナトリウム、炭酸水素カリウムのような炭酸水素塩;水酸化ナトリウム、水酸化カリウムのような金属水酸化物;水素化ナトリウム、水素化カリウムのような金属水素化物;トリエチルアミン、N,N-ジイソプロピルエチルアミンのようなアミン類;ピリジン、4-ジメチルアミノピリジン、2,6-ルチジンのようなピリジン類;酢酸ナトリウム、酢酸カリウムなどのアルカリ金属カルボン酸塩;などが挙げられる。
反応Eにおける脱水剤は、例えば、無水硫酸マグネシウム、無水硫酸ナトリウム、モレキュラーシーブスなどが挙げられる。 The acid in reaction E may be either an inorganic acid or an organic acid, and examples of the inorganic acid include hydrochloric acid and sulfuric acid, and examples of the organic acid include acetic acid, methanesulfonic acid, and paratoluenesulfonic acid.
The base in reaction E can be, for example, an alkali metal alkoxide such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; carbonate such as sodium carbonate, potassium carbonate; hydrogen carbonate such as sodium hydrogen carbonate, potassium hydrogen carbonate. Salts; Metal hydroxides such as sodium hydroxide and potassium hydroxide; Metal hydrides such as sodium hydride and potassium hydride; Amines such as triethylamine and N,N-diisopropylethylamine; Pyridine, 4-dimethyl Examples include pyridines such as aminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate; and the like.
Examples of the dehydrating agent in reaction E include anhydrous magnesium sulfate, anhydrous sodium sulfate, and molecular sieves.
反応Eにおける塩基は、例えば、ナトリウムメトキシド、ナトリウムエトキシド、カリウムtert-ブトキシドのようなアルカリ金属アルコキシド;炭酸ナトリウム、炭酸カリウムのような炭酸塩;炭酸水素ナトリウム、炭酸水素カリウムのような炭酸水素塩;水酸化ナトリウム、水酸化カリウムのような金属水酸化物;水素化ナトリウム、水素化カリウムのような金属水素化物;トリエチルアミン、N,N-ジイソプロピルエチルアミンのようなアミン類;ピリジン、4-ジメチルアミノピリジン、2,6-ルチジンのようなピリジン類;酢酸ナトリウム、酢酸カリウムなどのアルカリ金属カルボン酸塩;などが挙げられる。
反応Eにおける脱水剤は、例えば、無水硫酸マグネシウム、無水硫酸ナトリウム、モレキュラーシーブスなどが挙げられる。 The acid in reaction E may be either an inorganic acid or an organic acid, and examples of the inorganic acid include hydrochloric acid and sulfuric acid, and examples of the organic acid include acetic acid, methanesulfonic acid, and paratoluenesulfonic acid.
The base in reaction E can be, for example, an alkali metal alkoxide such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; carbonate such as sodium carbonate, potassium carbonate; hydrogen carbonate such as sodium hydrogen carbonate, potassium hydrogen carbonate. Salts; Metal hydroxides such as sodium hydroxide and potassium hydroxide; Metal hydrides such as sodium hydride and potassium hydride; Amines such as triethylamine and N,N-diisopropylethylamine; Pyridine, 4-dimethyl Examples include pyridines such as aminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate; and the like.
Examples of the dehydrating agent in reaction E include anhydrous magnesium sulfate, anhydrous sodium sulfate, and molecular sieves.
反応Eにおける溶媒は、反応に不活性な溶媒であればいずれのものでもよく、例えば、ジクロロメタン、クロロホルムのような脂肪族ハロゲン化炭化水素類;トルエン、キシレンのような芳香族炭化水素類;ジオキサン、テトラヒドロフラン、ジエチルエーテル、ジメトキシエタンのようなエーテル類;酢酸メチル、酢酸エチルのようなエステル類;アセトニトリルのような非プロトン性極性溶媒;メタノール、エタノールのようなプロトン性極性溶媒;水;などから1種又は2種以上を適宜選択することができる。
The solvent in reaction E may be any solvent as long as it is inert to the reaction; for example, aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; aromatic hydrocarbons such as toluene and xylene; dioxane. , ethers such as tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as acetonitrile; protic polar solvents such as methanol and ethanol; water; etc. One type or two or more types can be selected as appropriate.
反応Eの反応温度は、通常、-20℃~150℃程度、望ましくは0℃~120℃程度であり、反応時間は、通常0.5~48時間程度、望ましくは1~24時間程度である。
The reaction temperature for reaction E is usually about -20°C to 150°C, preferably about 0°C to 120°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours. .
反応Eで使用される式(IV-a)又は式(IV-b)の化合物は、公知の方法に準じて製造することができ、又は市販品を使用しても良い。
The compound of formula (IV-a) or formula (IV-b) used in reaction E can be produced according to a known method, or a commercially available product may be used.
反応Fは、通常、還元剤及び溶媒の存在下で、必要に応じて酸を添加して行うことができる。また、反応Fは、水素雰囲気下、パラジウム炭素を触媒として水素添加することで行うこともできる。
Reaction F can usually be carried out in the presence of a reducing agent and a solvent, with the addition of an acid if necessary. Further, reaction F can also be carried out by hydrogenation in a hydrogen atmosphere using palladium on carbon as a catalyst.
反応Fにおける還元剤は、例えば、水素化ホウ素ナトリウム、水素化シアノホウ素ナトリウム、水素化トリアセトキシホウ素ナトリウム、2-ピコリン・ボラン錯体などが挙げられる。還元剤は式(XX-g)の化合物1当量に対して、0.5~10当量、望ましくは1~5当量使用できる。前記酸は、無機酸、有機酸いずれでもよく、無機酸としては塩酸など、有機酸としては酢酸、トリフルオロ酢酸などが挙げられる。酸は式(XX-g)の化合物1当量に対して、1~10当量使用できる。
Examples of the reducing agent in reaction F include sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, and 2-picoline-borane complex. The reducing agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of formula (XX-g). The acid may be either an inorganic acid or an organic acid, and examples of the inorganic acid include hydrochloric acid, and examples of the organic acid include acetic acid and trifluoroacetic acid. The acid can be used in an amount of 1 to 10 equivalents per equivalent of the compound of formula (XX-g).
還元剤を用いて行う場合に用いる溶媒は、反応に不活性な溶媒であればいずれのものでもよく、例えば、ベンゼン、トルエン、キシレン、クロロベンゼンのような芳香族炭化水素類;四塩化炭素、塩化メチル、クロロホルム、ジクロロメタン、ジクロロエタン、トリクロロエタン、ヘキサン、シクロヘキサンのような脂肪族炭化水素類;ジオキサン、テトラヒドロフラン、ジエチルエーテル、ジメトキシエタンのようなエーテル類;酢酸メチル、酢酸エチルのようなエステル類;メタノール、エタノールのようなプロトン性極性溶媒;水;などから1種又は2種以上を適宜選択できる。
The solvent used when using a reducing agent may be any solvent as long as it is inert to the reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, chloride, etc. Aliphatic hydrocarbons such as methyl, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; methanol, One or more types can be appropriately selected from protic polar solvents such as ethanol; water; and the like.
水素雰囲気下、パラジウム炭素を触媒として反応させる場合に用いる溶媒は、反応に不活性な溶媒であればいずれのものでもよく、例えば、ジオキサン、テトラヒドロフラン、ジエチルエーテル、ジメトキシエタンのようなエーテル類;酢酸メチル、酢酸エチルのようなエステル類;メタノール、エタノール、イソプロパノールのようなアルコール類;水;などから1種又は2種以上を適宜選択できる。また、必要に応じて加圧条件下で行うこともできる。
The solvent used in the reaction using palladium on carbon as a catalyst in a hydrogen atmosphere may be any solvent as long as it is inert to the reaction, such as ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; acetic acid. One or more types can be appropriately selected from esters such as methyl and ethyl acetate; alcohols such as methanol, ethanol, and isopropanol; and water. Moreover, it can also be carried out under pressurized conditions if necessary.
反応Fの反応温度は、通常-20℃~150℃程度、望ましくは0℃~100℃程度であり、反応時間は、通常0.5~48時間程度、望ましくは1~24時間程度である。
The reaction temperature for reaction F is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.
[反応G]
反応Gは脱保護反応であり、式(XX-ga)の化合物のBoc基を除くことにより、式(XX-gb)の化合物を得る方法である。 [Reaction G]
Reaction G is a deprotection reaction, and is a method for obtaining a compound of formula (XX-gb) by removing the Boc group of the compound of formula (XX-ga).
反応Gは脱保護反応であり、式(XX-ga)の化合物のBoc基を除くことにより、式(XX-gb)の化合物を得る方法である。 [Reaction G]
Reaction G is a deprotection reaction, and is a method for obtaining a compound of formula (XX-gb) by removing the Boc group of the compound of formula (XX-ga).
式中の記号は前述の通りである。
反応Gは、上記反応Aに準じて行うことができる。 The symbols in the formula are as described above.
Reaction G can be carried out according to reaction A above.
反応Gは、上記反応Aに準じて行うことができる。 The symbols in the formula are as described above.
Reaction G can be carried out according to reaction A above.
[反応H]及び[反応I]
反応Hは、式(II)の化合物と式(V)の化合物を反応させ式(XX-g)の化合物を得る方法である。反応Iは、式(II-a)の化合物と式(V)の化合物を反応させ式(XX-g)の化合物を得る方法である。 [Reaction H] and [Reaction I]
Reaction H is a method of reacting a compound of formula (II) with a compound of formula (V) to obtain a compound of formula (XX-g). Reaction I is a method in which a compound of formula (II-a) and a compound of formula (V) are reacted to obtain a compound of formula (XX-g).
反応Hは、式(II)の化合物と式(V)の化合物を反応させ式(XX-g)の化合物を得る方法である。反応Iは、式(II-a)の化合物と式(V)の化合物を反応させ式(XX-g)の化合物を得る方法である。 [Reaction H] and [Reaction I]
Reaction H is a method of reacting a compound of formula (II) with a compound of formula (V) to obtain a compound of formula (XX-g). Reaction I is a method in which a compound of formula (II-a) and a compound of formula (V) are reacted to obtain a compound of formula (XX-g).
式中の記号は前述の通りである。
反応Hは、上記反応Bに準じて行うことができる。式(V)の化合物は、式(II)の化合物1当量に対して、0.5~3当量、望ましくは0.8~1.5当量使用できる。 The symbols in the formula are as described above.
Reaction H can be carried out according to reaction B above. The compound of formula (V) can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of formula (II).
反応Hは、上記反応Bに準じて行うことができる。式(V)の化合物は、式(II)の化合物1当量に対して、0.5~3当量、望ましくは0.8~1.5当量使用できる。 The symbols in the formula are as described above.
Reaction H can be carried out according to reaction B above. The compound of formula (V) can be used in an amount of 0.5 to 3 equivalents, preferably 0.8 to 1.5 equivalents, per equivalent of the compound of formula (II).
反応Iは、上記反応Cに準じて行うことができる。式(V)の化合物は、式(II-a)の化合物1当量に対して、0.5~3当量、望ましくは0.7~1.5当量使用できる。
Reaction I can be carried out according to reaction C above. The compound of formula (V) can be used in an amount of 0.5 to 3 equivalents, preferably 0.7 to 1.5 equivalents, per 1 equivalent of the compound of formula (II-a).
反応Hと反応Iで使用される式(V)の化合物は、下記反応2-5又は公知の方法に準じて製造することができ、又は市販品を使用しても良い。
The compound of formula (V) used in Reaction H and Reaction I can be produced according to Reaction 2-5 below or a known method, or a commercially available product may be used.
[反応J]
反応Jは、式(XX-i)の化合物を式(VI)の化合物と反応させることにより、式(XX-j)の化合物を得る方法である。 [Reaction J]
Reaction J is a method for obtaining a compound of formula (XX-j) by reacting a compound of formula (XX-i) with a compound of formula (VI).
反応Jは、式(XX-i)の化合物を式(VI)の化合物と反応させることにより、式(XX-j)の化合物を得る方法である。 [Reaction J]
Reaction J is a method for obtaining a compound of formula (XX-j) by reacting a compound of formula (XX-i) with a compound of formula (VI).
式中、L1は脱離基であり、例えば、ハロゲン、トリフルオロメタンスルホニルオキシ、メタンスルホニルオキシ、パラトルエンスルホニルオキシなどが挙げられ、R3cは(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、(C2-C4)-ハロアルケニル、(C3-C4)-シクロアルキル、又は少なくとも1個のZで置換された(C1-C3)-アルキルであり、その他の記号は前述の通りである。
In the formula, L 1 is a leaving group such as halogen, trifluoromethanesulfonyloxy, methanesulfonyloxy, paratoluenesulfonyloxy, etc., and R 3c is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 3 -C 4 )-cycloalkyl, or (substituted with at least one Z) C 1 -C 3 )-alkyl, and the other symbols are as described above.
反応Jは、通常、塩基及び溶媒の存在下で、必要に応じて相間移動触媒を添加して行うことができる。式(VI)の化合物は、式(XX-i)の化合物1当量に対して、1~5当量、望ましくは1~3当量使用できる。
Reaction J can usually be carried out in the presence of a base and a solvent, with the addition of a phase transfer catalyst if necessary. The compound of formula (VI) can be used in an amount of 1 to 5 equivalents, preferably 1 to 3 equivalents, per 1 equivalent of the compound of formula (XX-i).
反応Jにおける塩基は、例えば、ナトリウムメトキシド、ナトリウムエトキシド、カリウムtert-ブトキシドのようなアルカリ金属アルコキシド;炭酸ナトリウム、炭酸カリウムのような炭酸塩;炭酸水素ナトリウム、炭酸水素カリウムのような炭酸水素塩;水酸化ナトリウム、水酸化カリウムのような金属水酸化物;水素化ナトリウム、水素化カリウムのような金属水素化物;トリエチルアミン、N,N-ジイソプロピルエチルアミンのようなアミン類;ピリジン、4-ジメチルアミノピリジン、2,6-ルチジンのようなピリジン類;n-ブチルリチウム、リチウムジイソプロピルアミドのような有機リチウム化合物;酢酸ナトリウム、酢酸カリウムなどのアルカリ金属カルボン酸塩;などから1種又は2種以上を適宜選択、混合して使用することができる。塩基は、式(XX-i)の化合物1当量に対し1~10当量、望ましくは1~5当量使用できる。
反応Jにおける溶媒は、反応に不活性な溶媒であればいずれのものでもよく、例えば、ベンゼン、トルエン、キシレン、クロロベンゼンのような芳香族炭化水素類;四塩化炭素、塩化メチル、クロロホルム、ジクロロメタン、ジクロロエタン、トリクロロエタン、ヘキサン、シクロヘキサンのような脂肪族炭化水素類;ジオキサン、テトラヒドロフラン、ジエチルエーテル、ジメトキシエタンのようなエーテル類;酢酸メチル、酢酸エチルのようなエステル類;メタノール、エタノール、プロパノール、tert-ブタノールのようなアルコール類;ジメチルスルホキシド、スルホラン、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、N-メチルピロリドン、ピリジン、アセトニトリル、プロピオニトリルのような非プロトン性極性溶媒;アセトン、メチルエチルケトンのようなケトン類;水;などから1種又は2種以上を適宜選択できる。
反応Jにおける相間移動触媒としては、例えば、テトラブチルアンモニウムブロミド、ベンジルトリエチルアンモニウムクロリド、硫酸水素テトラブチルアンモニウムのような第四級アンモニウム塩;18-クラウン-6-エーテルのようなクラウンエーテル類;などが挙げられる。相間移動触媒は、式(XX-i)の化合物1当量に対し0.1~3当量使用できる。 The base in reaction J can be, for example, an alkali metal alkoxide such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; carbonate such as sodium carbonate, potassium carbonate; hydrogen carbonate such as sodium hydrogen carbonate, potassium hydrogen carbonate. Salts; Metal hydroxides such as sodium hydroxide and potassium hydroxide; Metal hydrides such as sodium hydride and potassium hydride; Amines such as triethylamine and N,N-diisopropylethylamine; Pyridine, 4-dimethyl One or more of pyridines such as aminopyridine and 2,6-lutidine; organic lithium compounds such as n-butyllithium and lithium diisopropylamide; alkali metal carboxylates such as sodium acetate and potassium acetate; can be selected and mixed as appropriate. The base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, per 1 equivalent of the compound of formula (XX-i).
The solvent in reaction J may be any solvent as long as it is inert to the reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, Aliphatic hydrocarbons such as dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; methanol, ethanol, propanol, tert- Alcohols such as butanol; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, propionitrile; acetone, methyl ethyl ketone One or more types can be appropriately selected from ketones such as; water; and the like.
Examples of the phase transfer catalyst in reaction J include quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium chloride, and tetrabutylammonium hydrogen sulfate; crown ethers such as 18-crown-6-ether; etc. can be mentioned. The phase transfer catalyst can be used in an amount of 0.1 to 3 equivalents per equivalent of the compound of formula (XX-i).
反応Jにおける溶媒は、反応に不活性な溶媒であればいずれのものでもよく、例えば、ベンゼン、トルエン、キシレン、クロロベンゼンのような芳香族炭化水素類;四塩化炭素、塩化メチル、クロロホルム、ジクロロメタン、ジクロロエタン、トリクロロエタン、ヘキサン、シクロヘキサンのような脂肪族炭化水素類;ジオキサン、テトラヒドロフラン、ジエチルエーテル、ジメトキシエタンのようなエーテル類;酢酸メチル、酢酸エチルのようなエステル類;メタノール、エタノール、プロパノール、tert-ブタノールのようなアルコール類;ジメチルスルホキシド、スルホラン、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、N-メチルピロリドン、ピリジン、アセトニトリル、プロピオニトリルのような非プロトン性極性溶媒;アセトン、メチルエチルケトンのようなケトン類;水;などから1種又は2種以上を適宜選択できる。
反応Jにおける相間移動触媒としては、例えば、テトラブチルアンモニウムブロミド、ベンジルトリエチルアンモニウムクロリド、硫酸水素テトラブチルアンモニウムのような第四級アンモニウム塩;18-クラウン-6-エーテルのようなクラウンエーテル類;などが挙げられる。相間移動触媒は、式(XX-i)の化合物1当量に対し0.1~3当量使用できる。 The base in reaction J can be, for example, an alkali metal alkoxide such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; carbonate such as sodium carbonate, potassium carbonate; hydrogen carbonate such as sodium hydrogen carbonate, potassium hydrogen carbonate. Salts; Metal hydroxides such as sodium hydroxide and potassium hydroxide; Metal hydrides such as sodium hydride and potassium hydride; Amines such as triethylamine and N,N-diisopropylethylamine; Pyridine, 4-dimethyl One or more of pyridines such as aminopyridine and 2,6-lutidine; organic lithium compounds such as n-butyllithium and lithium diisopropylamide; alkali metal carboxylates such as sodium acetate and potassium acetate; can be selected and mixed as appropriate. The base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, per 1 equivalent of the compound of formula (XX-i).
The solvent in reaction J may be any solvent as long as it is inert to the reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, Aliphatic hydrocarbons such as dichloroethane, trichloroethane, hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; methanol, ethanol, propanol, tert- Alcohols such as butanol; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, propionitrile; acetone, methyl ethyl ketone One or more types can be appropriately selected from ketones such as; water; and the like.
Examples of the phase transfer catalyst in reaction J include quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium chloride, and tetrabutylammonium hydrogen sulfate; crown ethers such as 18-crown-6-ether; etc. can be mentioned. The phase transfer catalyst can be used in an amount of 0.1 to 3 equivalents per equivalent of the compound of formula (XX-i).
反応Jの反応温度は、通常-20℃~150℃程度、望ましくは0℃~100℃程度であり、反応時間は、通常10分~48時間程度、望ましくは1~24時間程度である。
The reaction temperature for reaction J is usually about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 10 minutes to 48 hours, preferably about 1 to 24 hours.
反応Jで使用される式(VI)の化合物は、公知の方法に準じて製造することができ、又は市販品を使用しても良い。
The compound of formula (VI) used in reaction J can be produced according to a known method, or a commercially available product may be used.
[反応K]
反応Kは、式(II-b)の化合物を式(VII)の化合物と反応させることにより、式(XX-b)の化合物を得る方法である。 [Reaction K]
Reaction K is a method for obtaining a compound of formula (XX-b) by reacting a compound of formula (II-b) with a compound of formula (VII).
反応Kは、式(II-b)の化合物を式(VII)の化合物と反応させることにより、式(XX-b)の化合物を得る方法である。 [Reaction K]
Reaction K is a method for obtaining a compound of formula (XX-b) by reacting a compound of formula (II-b) with a compound of formula (VII).
式中の記号は前述の通りである。
The symbols in the formula are as described above.
反応Kは、上記反応Jに準じて行うことができる。式(VII)の化合物は、式(II-b)の化合物1当量に対して、1~5当量、望ましくは1~2当量使用できる。
Reaction K can be carried out according to the above reaction J. The compound of formula (VII) can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, per 1 equivalent of the compound of formula (II-b).
反応Kで使用される式(II-b)の化合物は、下記反応1-3又は公知の方法に準じて製造することができ、又は市販品を使用しても良い。反応Kで使用される式(VII)の化合物は、公知の方法に準じて製造することができ、又は市販品を使用しても良い。
The compound of formula (II-b) used in reaction K can be produced according to reaction 1-3 below or a known method, or a commercially available product may be used. The compound of formula (VII) used in reaction K can be produced according to a known method, or a commercially available product may be used.
[反応L]
反応Lは、式(XX-k)の化合物の加水分解を行い、式(XX-l)の化合物を得る方法である。 [Reaction L]
Reaction L is a method of hydrolyzing a compound of formula (XX-k) to obtain a compound of formula (XX-l).
反応Lは、式(XX-k)の化合物の加水分解を行い、式(XX-l)の化合物を得る方法である。 [Reaction L]
Reaction L is a method of hydrolyzing a compound of formula (XX-k) to obtain a compound of formula (XX-l).
R3dは少なくとも1個のZ1で置換された(C1-C3)-アルキルであり、Z1は-C(=O)RZ1であり、RZ1は(C3-C6)-シクロアルキルオキシ、(C1-C4)-アルコキシ、フェノキシ、又はベンジルオキシであり、R3eは、少なくとも1個のカルボキシ基で置換された(C1-C3)-アルキルである。その他の記号は前述の通りである。
R 3d is (C 1 -C 3 )-alkyl substituted with at least one Z 1 , Z 1 is -C(=O)R Z1 , and R Z1 is (C 3 -C 6 )- cycloalkyloxy, (C 1 -C 4 )-alkoxy, phenoxy or benzyloxy, and R 3e is (C 1 -C 3 )-alkyl substituted with at least one carboxy group. Other symbols are as described above.
反応Lは、一般的なエステルの塩基性加水分解の条件、例えば、Tetrahedron、2012、68、4682-4692に記載の方法に準じて行うことができる。
Reaction L can be carried out according to the general basic hydrolysis conditions of esters, for example, the method described in Tetrahedron, 2012, 68, 4682-4692.
製造方法1(反応A~反応L)で使用した化合物は、下記の製造方法2(反応1-1~反応1-3及び反応2-1~反応2-6)及び通常の塩の製造方法に従って製造することができるが、これらの方法に限定されるものではなく、これらの化合物は、公知の方法に準じて製造しても良く、又は市販品を使用しても良い。
The compounds used in Production Method 1 (Reactions A to Reactions L) were prepared according to the following Production Method 2 (Reactions 1-1 to 1-3 and Reactions 2-1 to 2-6) and ordinary salt production methods. However, these compounds are not limited to these methods, and these compounds may be produced according to known methods, or commercially available products may be used.
製造方法2
[反応1-1]、[反応1-2]及び[反応1-3]
反応1-1は、式(1)の化合物を酸化し式(II)の化合物を得る方法である。反応1-2は、式(2)の化合物を加水分解し式(II)の化合物を得る方法である。反応1-3は式(II)の化合物又は式(II-a)の化合物を式(3)の化合物と反応させ式(II-b)の化合物を得る方法である。 Manufacturing method 2
[Reaction 1-1], [Reaction 1-2] and [Reaction 1-3]
Reaction 1-1 is a method of oxidizing a compound of formula (1) to obtain a compound of formula (II). Reaction 1-2 is a method of hydrolyzing the compound of formula (2) to obtain the compound of formula (II). Reaction 1-3 is a method in which a compound of formula (II) or a compound of formula (II-a) is reacted with a compound of formula (3) to obtain a compound of formula (II-b).
[反応1-1]、[反応1-2]及び[反応1-3]
反応1-1は、式(1)の化合物を酸化し式(II)の化合物を得る方法である。反応1-2は、式(2)の化合物を加水分解し式(II)の化合物を得る方法である。反応1-3は式(II)の化合物又は式(II-a)の化合物を式(3)の化合物と反応させ式(II-b)の化合物を得る方法である。 Manufacturing method 2
[Reaction 1-1], [Reaction 1-2] and [Reaction 1-3]
Reaction 1-1 is a method of oxidizing a compound of formula (1) to obtain a compound of formula (II). Reaction 1-2 is a method of hydrolyzing the compound of formula (2) to obtain the compound of formula (II). Reaction 1-3 is a method in which a compound of formula (II) or a compound of formula (II-a) is reacted with a compound of formula (3) to obtain a compound of formula (II-b).
式中の記号は前述の通りである。
反応1-1は、一般的なピニック酸化の条件、例えば、Bioorganic & Medicinal Chemistry、2004、12、6171-6182に記載の方法に準じて行うことができる。 The symbols in the formula are as described above.
Reaction 1-1 can be carried out under general pinic oxidation conditions, for example, according to the method described in Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182.
反応1-1は、一般的なピニック酸化の条件、例えば、Bioorganic & Medicinal Chemistry、2004、12、6171-6182に記載の方法に準じて行うことができる。 The symbols in the formula are as described above.
Reaction 1-1 can be carried out under general pinic oxidation conditions, for example, according to the method described in Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182.
反応1-1で使用される式(1)の化合物は、公知の方法、例えば、Bioorganic & Medicinal Chemistry,2004,12、6171-6182、Journal of Organic Chemistry,2005,70,567-574、国際公開第2020/028141号、又はOrganic Process Research and Development,2021,25,1167-1175に記載の方法に準じて製造することができ、又は市販品を使用しても良い。
The compound of formula (1) used in reaction 1-1 can be prepared by a known method, for example, Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182, Journal of Organic Chemistry, 2005, 7 0,567-574, International Publication It can be produced according to the method described in No. 2020/028141 or Organic Process Research and Development, 2021, 25, 1167-1175, or a commercially available product may be used.
反応1-2は、一般的なエステルの加水分解の条件、例えば、国際公開第2009/100171号に記載の方法に準じて行うことができる。
Reaction 1-2 can be carried out under general ester hydrolysis conditions, for example, according to the method described in International Publication No. 2009/100171.
反応1-2で使用される式(2)の化合物は、公知の方法、例えば、国際公開第2012/006760号に記載の方法に準じて製造することができ、又は市販品を使用しても良い。
The compound of formula (2) used in reaction 1-2 can be produced according to a known method, for example, the method described in International Publication No. 2012/006760, or it can be produced using a commercially available product. good.
反応1-3は、上記反応B又は反応Cに準じて行うことができる。式(3)の化合物は、式(II)の化合物又は式(II‐a)の化合物1当量に対して、0.5~10当量、望ましくは0.7~5当量使用できる。
Reaction 1-3 can be carried out according to reaction B or reaction C above. The compound of formula (3) can be used in an amount of 0.5 to 10 equivalents, preferably 0.7 to 5 equivalents, per equivalent of the compound of formula (II) or the compound of formula (II-a).
反応1-3で使用される式(3)の化合物は、公知の方法に準じて、例えば、European Journal of Organic Chemistry,2003,4757-4764、Synthetic Communications、2017、47、1231-1238に記載の方法に準じて製造することができ、又は市販品を使用しても良い。
The compound of formula (3) used in reaction 1-3 can be prepared according to known methods, for example, European Journal of Organic Chemistry, 2003, 4757-4764, Synthetic Communications, 2017, 4 7, 1231-1238. It can be manufactured according to the method, or a commercially available product may be used.
[反応2-1]~[反応2-6]
反応2-1は式(10)の化合物を式(3)の化合物と反応させ式(11)の化合物を得る方法である。反応2-2は式(11)の化合物を還元し、式(III)の化合物を得る方法である。反応2-1と反応2-2は式(11)の化合物を単離することなく、連続して行うこともできる。
反応2-3は、式(11-a)の化合物を式(VI)の化合物と反応させることにより、式(11-b)の化合物を得る方法である。
反応2-4は、式(VII)の化合物を式(3)の化合物と反応させることにより、式(III)の化合物を得る方法である。
反応2-5は式(III-a)の化合物を式(IV-a)の化合物又は式(IV-b)の化合物と反応させ式(V)の化合物を得る方法である。反応2-6は、式(V)の化合物を還元し式(III-b)の化合物を得る方法である。反応2-5と反応2-6は式(V)の化合物を単離することなく、連続して行うこともできる。 [Reaction 2-1] to [Reaction 2-6]
Reaction 2-1 is a method in which a compound of formula (10) is reacted with a compound of formula (3) to obtain a compound of formula (11). Reaction 2-2 is a method for reducing the compound of formula (11) to obtain the compound of formula (III). Reactions 2-1 and 2-2 can also be carried out consecutively without isolating the compound of formula (11).
Reaction 2-3 is a method for obtaining a compound of formula (11-b) by reacting a compound of formula (11-a) with a compound of formula (VI).
Reaction 2-4 is a method for obtaining a compound of formula (III) by reacting a compound of formula (VII) with a compound of formula (3).
Reaction 2-5 is a method in which a compound of formula (III-a) is reacted with a compound of formula (IV-a) or a compound of formula (IV-b) to obtain a compound of formula (V). Reaction 2-6 is a method of reducing the compound of formula (V) to obtain the compound of formula (III-b). Reactions 2-5 and 2-6 can also be carried out consecutively without isolating the compound of formula (V).
反応2-1は式(10)の化合物を式(3)の化合物と反応させ式(11)の化合物を得る方法である。反応2-2は式(11)の化合物を還元し、式(III)の化合物を得る方法である。反応2-1と反応2-2は式(11)の化合物を単離することなく、連続して行うこともできる。
反応2-3は、式(11-a)の化合物を式(VI)の化合物と反応させることにより、式(11-b)の化合物を得る方法である。
反応2-4は、式(VII)の化合物を式(3)の化合物と反応させることにより、式(III)の化合物を得る方法である。
反応2-5は式(III-a)の化合物を式(IV-a)の化合物又は式(IV-b)の化合物と反応させ式(V)の化合物を得る方法である。反応2-6は、式(V)の化合物を還元し式(III-b)の化合物を得る方法である。反応2-5と反応2-6は式(V)の化合物を単離することなく、連続して行うこともできる。 [Reaction 2-1] to [Reaction 2-6]
Reaction 2-1 is a method in which a compound of formula (10) is reacted with a compound of formula (3) to obtain a compound of formula (11). Reaction 2-2 is a method for reducing the compound of formula (11) to obtain the compound of formula (III). Reactions 2-1 and 2-2 can also be carried out consecutively without isolating the compound of formula (11).
Reaction 2-3 is a method for obtaining a compound of formula (11-b) by reacting a compound of formula (11-a) with a compound of formula (VI).
Reaction 2-4 is a method for obtaining a compound of formula (III) by reacting a compound of formula (VII) with a compound of formula (3).
Reaction 2-5 is a method in which a compound of formula (III-a) is reacted with a compound of formula (IV-a) or a compound of formula (IV-b) to obtain a compound of formula (V). Reaction 2-6 is a method of reducing the compound of formula (V) to obtain the compound of formula (III-b). Reactions 2-5 and 2-6 can also be carried out consecutively without isolating the compound of formula (V).
式中の記号は前述の通りである。
反応2-1は、一般的なアルデヒドとヒドラジンによるヒドラゾン化の条件、例えば、Tetrahedron Letters,2013,54,896-899に記載の方法に準じて行うことができる。式(3)の化合物は、式(10)の化合物1当量に対して、0.7~5当量、望ましくは1~2当量使用できる。 The symbols in the formula are as described above.
Reaction 2-1 can be carried out according to general hydrazonation conditions using an aldehyde and hydrazine, for example, the method described in Tetrahedron Letters, 2013, 54, 896-899. The compound of formula (3) can be used in an amount of 0.7 to 5 equivalents, preferably 1 to 2 equivalents, per 1 equivalent of the compound of formula (10).
反応2-1は、一般的なアルデヒドとヒドラジンによるヒドラゾン化の条件、例えば、Tetrahedron Letters,2013,54,896-899に記載の方法に準じて行うことができる。式(3)の化合物は、式(10)の化合物1当量に対して、0.7~5当量、望ましくは1~2当量使用できる。 The symbols in the formula are as described above.
Reaction 2-1 can be carried out according to general hydrazonation conditions using an aldehyde and hydrazine, for example, the method described in Tetrahedron Letters, 2013, 54, 896-899. The compound of formula (3) can be used in an amount of 0.7 to 5 equivalents, preferably 1 to 2 equivalents, per 1 equivalent of the compound of formula (10).
反応2-1で使用される式(10)の化合物は、公知の方法に準じて製造でき、又は市販品を使用しても良い。
The compound of formula (10) used in reaction 2-1 can be produced according to a known method, or a commercially available product may be used.
反応2-2は、一般的なヒドラゾンをヒドラジンに還元する条件、例えば、米国特許出願公開第2016/002251号、Chemical Reviews,2019,119,11857-11911に記載の方法に準じて行うことができる。2-ピコリン・ボラン錯体を用いて、必要に応じて塩酸などの酸を添加して、還元することもできる。
Reaction 2-2 can be carried out under general conditions for reducing hydrazone to hydrazine, for example, according to the method described in U.S. Patent Application Publication No. 2016/002251, Chemical Reviews, 2019, 119, 11857-11911. . It is also possible to reduce the 2-picoline/borane complex by adding an acid such as hydrochloric acid as necessary.
反応2-3は、公知のヒドラゾンのアルキル化条件、例えば、Organic Letters,2014,16,5940-5943、Chemistry‐A European Jornal,2019,25,976-980、Journal of Organic Chemistry,2006,71,7113-7116などに記載の方法に準じて行うことができる。
Reaction 2-3 is performed under known hydrazone alkylation conditions, for example, Organic Letters, 2014, 16, 5940-5943, Chemistry-A European Journal, 2019, 25, 976-980, Journal of Or ganic Chemistry, 2006, 71, 7113-7116, etc.
反応2-4は、公知のヒドラジンのアルキル化反応、例えば、米国特許出願公開第2012/0157386号、Organic Letters,2014,16,4782-4785、国際公開第2018/221679号などに記載の方法に準じて行うことができる。
Reaction 2-4 is a known alkylation reaction of hydrazine, for example, the method described in US Patent Application Publication No. 2012/0157386, Organic Letters, 2014, 16, 4782-4785, International Publication No. 2018/221679, etc. This can be done in accordance with the above.
反応2-5は、反応Eに準じて行うことができ、反応2-6は、反応Fに準じて行うことができる。
Reaction 2-5 can be carried out according to reaction E, and reaction 2-6 can be carried out according to reaction F.
本組成物の有効成分である化合物(I)は、低薬量で植物病害を防除できる農園芸用殺菌剤の有効成分として有用である。化合物(I)には化合物(IA)及び化合物(IB)が包含され、したがって以下の説明には、化合物(IA)及び化合物(IB)も含まれる。
化合物(I)は、例えば卵菌類(Oomycetes)、ネコブカビ類(Phytomyxea)、子嚢菌類(Ascomycetes)、担子菌類(Basidiomycetes)、不完全菌類(Deuteromycetes)などに属する植物病原菌に由来する植物病害を防除できる。その中で、卵菌類(Oomycetes)およびネコブカビ類(Phytomyxea)に属する植物病原菌に由来する植物病害の防除に特に有効である。 Compound (I), which is the active ingredient of the present composition, is useful as an active ingredient of an agricultural and horticultural fungicide that can control plant diseases with a low dose. Compound (I) includes compound (IA) and compound (IB), and therefore, the following description also includes compound (IA) and compound (IB).
Compound (I) controls plant diseases caused by plant pathogenic fungi belonging to, for example, Oomycetes, Phytomyxea, Ascomycetes, Basidiomycetes, Deuteromycetes, etc. can. Among them, it is particularly effective for controlling plant diseases derived from plant pathogenic fungi belonging to the Oomycetes and Phytomyxea.
化合物(I)は、例えば卵菌類(Oomycetes)、ネコブカビ類(Phytomyxea)、子嚢菌類(Ascomycetes)、担子菌類(Basidiomycetes)、不完全菌類(Deuteromycetes)などに属する植物病原菌に由来する植物病害を防除できる。その中で、卵菌類(Oomycetes)およびネコブカビ類(Phytomyxea)に属する植物病原菌に由来する植物病害の防除に特に有効である。 Compound (I), which is the active ingredient of the present composition, is useful as an active ingredient of an agricultural and horticultural fungicide that can control plant diseases with a low dose. Compound (I) includes compound (IA) and compound (IB), and therefore, the following description also includes compound (IA) and compound (IB).
Compound (I) controls plant diseases caused by plant pathogenic fungi belonging to, for example, Oomycetes, Phytomyxea, Ascomycetes, Basidiomycetes, Deuteromycetes, etc. can. Among them, it is particularly effective for controlling plant diseases derived from plant pathogenic fungi belonging to the Oomycetes and Phytomyxea.
前記植物病原菌類の具体例としては、例えば以下のようなものなどが挙げられる。
卵菌類として、バレイショ又はトマト疫病菌(Phytophthora infestans)、イチジク疫病菌(Phytophthora palmivora)、ナシ又はイチゴ疫病菌(Phytophthora cactorum)、トウガン、カボチャ、ピーマン又はトウガラシ疫病菌(Phytophthora capsici)、トマト灰色疫病菌(Phytophthora capsici)、ナス又はスイカ褐色腐敗病菌(Phytophthora capsici)、カンキツ褐色腐敗病菌(Phytophthora citricola)、アズキ茎疫病菌(Phytophthora vignae f. sp. adzukicola)、エダマメ茎疫病菌(Phytophthora megasperma var. sojae)、タマネギ又はラッキョウ白色疫病(Phytophthora porri)のようなフィトフトラ(Phytophthora)属菌;キュウリ、カボチャ、メロン、ズッキーニべと病菌(Pseudoperonospora cubensis)、ホップべと病菌(Pseudoperonospora humuli)のようなシュードペロノスポラ(Pseudoperonospora)属菌;ブドウべと病菌(Plasmopara viticola)、ミツバべと病菌(Plasmopara nivea)のようなプラズモパラ(Plasmopara)属菌;キャベツ又はハクサイべと病菌のようなヒアロペロノスポラ(Hyaloperonospora)属菌;レタスべと病菌(Bremia lactucae)のようなブレミア(Bremia)属菌;イネ苗立枯病菌(Pythium graminicola)、コムギ褐色雪腐病菌(Pythium iwayamai)、ハクサイピシウム腐敗病菌(Pythium aphanidermatum)、ミョウガ根茎腐敗病菌(Pythium zingiberis)、ショウガ根茎腐敗病菌(Pythium ultimum var. ultimum)のようなピシウム(Pythium)属菌;ダイコン根くびれ病菌Aphanomyces raphani)、ホウレンソウ根腐病菌(Aphanomyces cochlioides)のようなアファノミセス(Aphanomyces)属菌;ホウレンソウ、カブ、ダイコン又はナバナ白さび病菌(Albugo macrospora)、ワサビ白さび病菌(Albugo wasabiae)、エンサイ白さび病菌(Albugo ipomoeae-aquaticae)のようなアルブゴ(Albugo)属菌;ダイズ又はエダマメべと病菌(Peronospora manshurica)、ブロッコリー又はカブべと病菌(Peronospora parasitica)、ネギ、ワケギ又はタマネギべと病菌(Peronospora destructor)、ホウレンソウべと病菌(Peronospora farinosa f. sp. Spinaciae)、バジルべと病菌(Peronospora belbahrii)のようなペロノスポラ(Peronospora)属菌などが挙げられる。 Specific examples of the plant pathogenic fungi include the following.
Oomycetes include Phytophthora infestans , Phytophthora palmivora, Phytophthora cactorum , Phytophthora capsici , and Phytophthora capsici . ( Phytophthora capsici ), eggplant or watermelon brown rot fungus ( Phytophthora capsici ), citrus brown rot fungus ( Phytophthora citricola ), adzuki bean stem blight fungus ( Phytophthora vignae f. sp. adzukicola ), edamame stem blight fungus ( Phytophthora megasperma var. sojae ) Phytophthora, such as onion or Phytophthora porri ; Pseudoperonospora , such as cucumber, pumpkin, melon, zucchini downy mildew ( Pseudoperonospora cubensis ), hop downy mildew ( Pseudoperonospora humuli ) ( Pseudoperonospora ); Plasmopara (Pseudoperonospora) such as grape downy mildew ( Plasmopara viticol a), Mitsuba downy mildew ( Plasmopara nivea ); Hyaloperonospora ( Hyaloperonospora) such as cabbage or Chinese cabbage downy mildew Bacteria of the genus Bremia , such as lettuce downy mildew ( Bremia lactucae ); rice seedling damping-off fungus ( Pythium graminicola ), wheat brown snow rot fungus ( Pythium iwayamai ), Chinese cabbage rot fungus ( Pythium aphanidermatum ), Bacteria of the genus Pythium such as Pythium zingiberis and Pythium ultimum var. ultimum ; Aphanomycetes such as Aphanomyces raphani and Aphanomyces cochlioides of radish root rot. Fungi of the genus Aphanomyces ; fungi of the genus Albugo, such as spinach, turnip, radish or napa white rust ( Albugo macrospora ), wasabi white rust ( Albugo wasabiae ) , and Japanese white rust ( Albugo ipomoeae-aquaticae ); Soybean or edamame downy mildew ( Peronospora manshurica ), broccoli or turnip downy mildew ( Peronospora parasitica ), green onion, spring onion or onion downy mildew ( Peronospora destructor ), spinach downy mildew ( Peronospora farinosa f. sp. Spinaciae ), basil Examples include bacteria of the genus Peronospora, such as downy mildew (Peronospora belbahrii ) .
卵菌類として、バレイショ又はトマト疫病菌(Phytophthora infestans)、イチジク疫病菌(Phytophthora palmivora)、ナシ又はイチゴ疫病菌(Phytophthora cactorum)、トウガン、カボチャ、ピーマン又はトウガラシ疫病菌(Phytophthora capsici)、トマト灰色疫病菌(Phytophthora capsici)、ナス又はスイカ褐色腐敗病菌(Phytophthora capsici)、カンキツ褐色腐敗病菌(Phytophthora citricola)、アズキ茎疫病菌(Phytophthora vignae f. sp. adzukicola)、エダマメ茎疫病菌(Phytophthora megasperma var. sojae)、タマネギ又はラッキョウ白色疫病(Phytophthora porri)のようなフィトフトラ(Phytophthora)属菌;キュウリ、カボチャ、メロン、ズッキーニべと病菌(Pseudoperonospora cubensis)、ホップべと病菌(Pseudoperonospora humuli)のようなシュードペロノスポラ(Pseudoperonospora)属菌;ブドウべと病菌(Plasmopara viticola)、ミツバべと病菌(Plasmopara nivea)のようなプラズモパラ(Plasmopara)属菌;キャベツ又はハクサイべと病菌のようなヒアロペロノスポラ(Hyaloperonospora)属菌;レタスべと病菌(Bremia lactucae)のようなブレミア(Bremia)属菌;イネ苗立枯病菌(Pythium graminicola)、コムギ褐色雪腐病菌(Pythium iwayamai)、ハクサイピシウム腐敗病菌(Pythium aphanidermatum)、ミョウガ根茎腐敗病菌(Pythium zingiberis)、ショウガ根茎腐敗病菌(Pythium ultimum var. ultimum)のようなピシウム(Pythium)属菌;ダイコン根くびれ病菌Aphanomyces raphani)、ホウレンソウ根腐病菌(Aphanomyces cochlioides)のようなアファノミセス(Aphanomyces)属菌;ホウレンソウ、カブ、ダイコン又はナバナ白さび病菌(Albugo macrospora)、ワサビ白さび病菌(Albugo wasabiae)、エンサイ白さび病菌(Albugo ipomoeae-aquaticae)のようなアルブゴ(Albugo)属菌;ダイズ又はエダマメべと病菌(Peronospora manshurica)、ブロッコリー又はカブべと病菌(Peronospora parasitica)、ネギ、ワケギ又はタマネギべと病菌(Peronospora destructor)、ホウレンソウべと病菌(Peronospora farinosa f. sp. Spinaciae)、バジルべと病菌(Peronospora belbahrii)のようなペロノスポラ(Peronospora)属菌などが挙げられる。 Specific examples of the plant pathogenic fungi include the following.
Oomycetes include Phytophthora infestans , Phytophthora palmivora, Phytophthora cactorum , Phytophthora capsici , and Phytophthora capsici . ( Phytophthora capsici ), eggplant or watermelon brown rot fungus ( Phytophthora capsici ), citrus brown rot fungus ( Phytophthora citricola ), adzuki bean stem blight fungus ( Phytophthora vignae f. sp. adzukicola ), edamame stem blight fungus ( Phytophthora megasperma var. sojae ) Phytophthora, such as onion or Phytophthora porri ; Pseudoperonospora , such as cucumber, pumpkin, melon, zucchini downy mildew ( Pseudoperonospora cubensis ), hop downy mildew ( Pseudoperonospora humuli ) ( Pseudoperonospora ); Plasmopara (Pseudoperonospora) such as grape downy mildew ( Plasmopara viticol a), Mitsuba downy mildew ( Plasmopara nivea ); Hyaloperonospora ( Hyaloperonospora) such as cabbage or Chinese cabbage downy mildew Bacteria of the genus Bremia , such as lettuce downy mildew ( Bremia lactucae ); rice seedling damping-off fungus ( Pythium graminicola ), wheat brown snow rot fungus ( Pythium iwayamai ), Chinese cabbage rot fungus ( Pythium aphanidermatum ), Bacteria of the genus Pythium such as Pythium zingiberis and Pythium ultimum var. ultimum ; Aphanomycetes such as Aphanomyces raphani and Aphanomyces cochlioides of radish root rot. Fungi of the genus Aphanomyces ; fungi of the genus Albugo, such as spinach, turnip, radish or napa white rust ( Albugo macrospora ), wasabi white rust ( Albugo wasabiae ) , and Japanese white rust ( Albugo ipomoeae-aquaticae ); Soybean or edamame downy mildew ( Peronospora manshurica ), broccoli or turnip downy mildew ( Peronospora parasitica ), green onion, spring onion or onion downy mildew ( Peronospora destructor ), spinach downy mildew ( Peronospora farinosa f. sp. Spinaciae ), basil Examples include bacteria of the genus Peronospora, such as downy mildew (Peronospora belbahrii ) .
ネコブカビ類として、ハクサイ、キャベツ、カリフラワー、ナバナ、ブロッコリー又はカブ根こぶ病菌(Plasmodiophora brassicae)のようなネコブカビ(Plasmodiophora)属菌;テンサイそう根病ウイルス(Beet necrotic yellow vein virus)を媒介するポリミキサ ベタエ(Polymyxa betae)のようなポリミキサ(Polymyxa)属菌;バレイショ粉状そうか病菌(Spongospora subterranea)のようなスポンゴスポラ(Spongospora)属菌;
レタスビッグベイン病ウイルス(Mirafiori lettuce bigvein virus)を媒介するOlpidium virulentusのようなオルピディウム(Olpidium)属菌)などが挙げられる。 Plasmodiophora bacteria such as Chinese cabbage, cabbage, cauliflower, napa, broccoli or turnip clubroot ( Plasmodiophora brassicae ); Polymyxa betae ( Beet necrotic yellow vein virus ) which transmits beet necrotic yellow vein virus. Bacteria of the genus Polymyxa such as Polymyxa betae ; Bacteria of the genus Spongospora such as Spongospora subterranea ;
Examples include bacteria of the genus Olpidium, such as Olpidium virulentus, which transmits the lettuce bigvein virus.
レタスビッグベイン病ウイルス(Mirafiori lettuce bigvein virus)を媒介するOlpidium virulentusのようなオルピディウム(Olpidium)属菌)などが挙げられる。 Plasmodiophora bacteria such as Chinese cabbage, cabbage, cauliflower, napa, broccoli or turnip clubroot ( Plasmodiophora brassicae ); Polymyxa betae ( Beet necrotic yellow vein virus ) which transmits beet necrotic yellow vein virus. Bacteria of the genus Polymyxa such as Polymyxa betae ; Bacteria of the genus Spongospora such as Spongospora subterranea ;
Examples include bacteria of the genus Olpidium, such as Olpidium virulentus, which transmits the lettuce bigvein virus.
子嚢菌類として、コムギうどんこ病菌(Erysiphe graminis)のようなエリシフェ(Erysiphe)属菌;トウモロコシすす紋病菌(Setosphaeria turcica)のようなセトスフェリア(Setosphaeria)属菌;キュウリうどんこ病菌(Sphaerotheca fuliginea)、イチゴうどんこ病菌(Sphaerotheca humuli)のようなスファエロテカ(Sphaerotheca)属菌;ブドウうどんこ病菌(Uncinula necator)のようなウンシニュラ(Uncinula)属菌;リンゴうどんこ病菌(Podosphaera leucotricha)のようなポドスファエラ(Podosphaera)属菌;エンドウ褐紋病菌(Mycosphaerella pinodes)、リンゴ黒点病菌(Mycosphaerella pomi)、バナナブラックシガトカ病菌(Mycosphaerella musicola)、カキ円星落葉病菌(Mycosphaerella nawae)、イチゴ蛇の目病菌(Mycosphaerella fragariae)のようなミコスファエレラ(Mycosphaerella)属菌;リンゴ黒星病菌(Venturia inaequalis)、ナシ黒星病菌(Venturia nashicola)のようなヴェンチュリア(Venturia)属菌;オオムギ網斑病菌(Pyrenophora teres)、オオムギ斑葉病菌(Pyrenophora graminea)のようなピレノホラ(Pyrenophora)属菌;インゲン、キュウリ、キャベツ、ハクサイ、トウガラシ、ピーマン又はタマネギ菌核病菌(Sclerotinia sclerotiorum)、コムギ雪腐大粒菌核病菌(Sclerotinia borealis)、トマト小粒菌核病菌(Sclerotinia minor)、アルファルファ菌核病菌(Sclerotinia trifoliorum)のようなスクレロティニア(Sclerotinia)属菌;ラッカセイ小菌核病菌(Botryotinia arachidis)のようなボトリオチニア(Botryotinia)属菌;イネごま葉枯病菌(Cochliobolus miyabeanus)のようなコクリオボラス(Cochliobolus)属菌;キュウリつる枯病菌(Didymella bryoniae)のようなディディメラ(Didymella)属菌;イネ馬鹿苗病菌(Gibberella fujikuroi)のようなジベレラ(Gibberella)属菌;ブドウ黒痘病菌(Elsinoe ampelina)、カンキツそうか病菌(Elsinoe fawcettii)のようなエルシノエ(Elsinoe)属菌;カンキツ黒点病菌(Diaporthe citri)、ブドウ枝膨病菌(Diaporthe sp.)のようなディアポルテ(Diaporthe)属菌;リンゴモニリア病菌(Monilinia mali)、モモ灰星病菌(Monilinia fructicola)のようなモニリニア(Monilinia)属;ブドウ晩腐病菌(Glomerella cingulata)のようなグロメレラ(Glomerella)属菌などが挙げられる。
As ascomycetes, Erysiphe genus bacteria such as wheat powdery mildew ( Erysiphe graminis ); Setosphaeria genus bacteria such as corn soot spot fungus (Setosphaeria turcica); cucumber powdery mildew ( Sphaerotheca fuliginea ), Sphaerotheca such as strawberry powdery mildew ( Sphaerotheca humuli ); Uncinula such as grape powdery mildew ( Uncinula necator ); Podosphaera such as apple powdery mildew ( Podosphaera leucotricha ) ) genus; such as Mycosphaerella pinodes , Mycosphaerella pomi , Mycosphaerella musicola , Mycosphaerella nawae , and Mycosphaerella fragariae . Bacteria of the genus Mycosphaerella ; Bacteria of the genus Venturia , such as Venturia inaequalis and Venturia nashicola ; Pyrenophora teres , Pyrenophora graminea ); Sclerotinia sclerotiorum on beans, cucumbers, cabbage, Chinese cabbage, chili peppers, peppers or onions; Sclerotinia borealis on wheat; Sclerotinia borealis on tomatoes; Bacteria of the genus Sclerotinia such as Sclerotinia minor ) and Sclerotinia trifoliorum ; Bacteria of the genus Botryotinia such as Botryotinia arachidis; Cochliobolus Bacteria of the genus Cochliobolus such as Miyabeanus ; Bacteria of the genus Didymella such as Didymella bryoniae ; Bacteria of the genus Gibberella such as Gibberella fujikuroi ; Elsinoe fungi such as Elsinoe ampelina and Elsinoe fawcettii ; Diaporthe such as Diaporthe citri and Diaporthe sp. Bacteria of the genus Monilinia, such as Monilinia mali and Monilinia fructicola ; and Glomerella , such as Glomerella cingulata .
担子菌類として、イネ紋枯病菌(Rhizoctonia solani)のようなリゾクトニア(Rhizoctonia)属菌;コムギ裸黒穂病菌(Ustilago nuda)のようなウスチラゴ(Ustilago)属菌;エンバク冠さび病菌(Puccinia coronata)、コムギ赤さび病菌(Puccinia recondita)、コムギ黄さび病菌(Puccinia striiformis)のようなプクシニア(Puccinia)属菌;ダイズさび病菌(Phakopsora pachyrhizi)のようなファコプソラ(Phakopsora)属菌;コムギ又はオオムギ雪腐小粒菌核病菌(Typhula incarnata又はTyphula ishikariensis) のようなティフラ(Typhula)属菌などが挙げられる。
Examples of basidiomycetes include Rhizoctonia genus bacteria such as rice sheath blight fungus ( Rhizoctonia solani ); Ustilago genus fungi such as wheat naked smut fungus ( Ustilago nuda ); oat crown rust fungus ( Puccinia coronata ); Bacteria of the genus Puccinia such as Puccinia recondita and Puccinia striiformis ; Bacteria of the genus Phakopsora such as Phakopsora pachyrhizi ; small grain fungi of wheat or barley snow rot Examples include Typhula genus bacteria such as Typhula incarnata or Typhula ishikariensis .
不完全菌類として、コムギふ枯病菌(Septoria nodorum)、コムギ葉枯病菌(Septoria tritici)のようなセプトリア(Septoria)属菌;ブドウ、カンキツ、キュウリ、トマト、イチゴ、ナス、インゲン、アズキ、エンドウ、ラッカセイ、トウガラシ、ピーマン、レタス、タマネギ、スターチス、カーネーション、バラ、パンジー又はヒマワリ灰色かび病菌(Botrytis cinerea)、タマネギ灰色腐敗病菌(Botrytis allii)、タマネギのボトリティス属菌による葉枯れ症を引き起こす病原菌(Botrytis squamosa、Botrytis byssoidea又はBotrytis tulipae)のようなボトリティス(Botrytis)属菌;コムギ赤かび病菌(Fusarium graminearum)、キュウリつる割病菌(Fusarium oxysporum)のようなフザリウム(Fusarium)属菌;イネいもち病菌(Pyricularia oryzae)のようなピリキュラリア(Pyricularia)属菌;テンサイ褐斑病菌(Cercospora beticola)、カキ角斑病菌(Cercospora kakivora)のようなサーコスポラ(Cercospora)属菌;キュウリ炭そ病菌(Colletotrichum orbiculare)、コーヒーノキ(Colletotrichum coffeanum)のようなコレトトリカム(Colletotrichum)属菌;リンゴ斑点落葉病菌(Alternaria alternata apple pathotype)、ナシ黒斑病菌(Alternaria alternata Japanese pear pathotype)、バレイショ夏疫またはトマト輪紋病菌(Alternaria solani)、キャベツ又はハクサイ黒斑病菌(Alternaria brassicae)、キャベツ黒すす病菌(Alternaria brassicicola)、タマネギ又はネギ黒斑病菌(Alternaria porri)のようなアルタナリア(Alternaria)属菌;キャベツ根朽病菌(Phoma lingam)のようなフォーマ(Phoma)属菌;コムギ眼紋病菌(Pseudocercosporella herpotrichoides)のようなシュードサーコスポレラ(Pseudocercosporella)属菌;ブドウ褐斑病菌(Pseudocercospora vitis)のようなシュードサーコスポラ(Pseudocercospora)属菌;オオムギ雲形病菌(Rhynchosporium secalis)のようなリンコスポリウム(Rhynchosporium)属菌;モモ黒星病菌(Cladosporium carpophilum)のようなクラドスポリウム(Cladosporium)属菌;モモホモプシス腐敗病菌(Phomopsis sp.)のようなホモプシス(Phomopsis)属菌;カキ炭そ病菌(Gloeosporium kaki)のようなグロエオスポリウム(Gloeosporium)属菌;トマト葉かび病菌(Fulvia fulva)のようなフルビア(Fulvia)属菌;キュウリ褐斑病菌(Corynespora cassiicola)のようなコリネスポラ(Corynespora)属菌などが挙げられる。また、トウモロコシ斑点病菌 (Physoderma maydis) のような Physoderma 属菌類なども挙げられる。
Deuteromycetes include Septoria genus bacteria such as Septoria nodorum and Septoria tritici ; grapes, citrus, cucumbers, tomatoes, strawberries, eggplants, green beans, adzuki beans, peas, Botrytis cinerea on groundnuts , chili peppers, bell peppers, lettuce, onions, statice, carnations , roses, pansies or sunflowers, Botrytis allii on onions, Botrytis spp. Bacteria of the genus Botrytis such as squamosa , Botrytis byssoidea or Botrytis tulipae ; Bacteria of the genus Fusarium such as Fusarium graminearum and Fusarium oxysporum ; Pyricularia Bacteria of the genus Pyricularia such as Pyricularia oryzae ; Bacteria of the genus Cercospora such as Cercospora beticola and Cercospora kakivora ; Colletotrichum orbiculare of cucumber, and Bacteria of the genus Coffea Colletotrichum fungi such as Colletotrichum coffeanum ; Alternaria alternata apple pathotype, Alternaria alternata Japanese pear pathotype, Potato summer blight or Tomato ring spot fungus ( Alternaria solani ), Cabbage or Alternaria fungi such as Chinese cabbage black spot fungus ( Alternaria brassicae ), cabbage black sooty fungus ( Alternaria brassicicola ), onion or allium black spot fungus ( Alternaria porri ); cabbage root rot fungus ( Phoma lingam ) Bacteria of the genus Phoma ; Bacteria of the genus Pseudocercosporella such as Pseudocercosporella herpotrichoides ; Bacteria of the genus Pseudocercospora such as Pseudocercospora vitis; Bacteria of the genus Rhynchosporium , such as Rhynchosporium secalis ; Bacteria of the genus Cladosporium, such as Cladosporium carpophilum ; Homopsis, such as Phomopsis sp . Bacteria of the genus Gloeosporium such as Gloeosporium kaki ; Bacteria of the genus Fulvia such as Fulvia fulva ; Corynespora of cucumber Examples include Corynespora genus bacteria such as cassiicola ). Also included are fungi of the genus Physoderma, such as corn spot disease fungus (Physoderma maydis).
化合物(I)は前述した各種の植物病原菌類を防除できることから、本組成物は各種病害を予防的又は治療的に防除することができる。特に本組成物は、農園芸分野で問題となる各種病害、例えば、ピシウム菌による苗立枯病、ピリキュラリア菌によるいもち病、フザリウム菌による馬鹿苗病、コクリオボラス菌によるごま葉枯病、リゾクトニア菌による紋枯病等のイネの病害;エリシフェ菌によるうどんこ病、フザリウム菌による赤かび病又はクラウンロット病、プクシニア菌によるさび病、ピシウム菌による褐色雪腐病、ウスチラゴ菌による裸黒穂病、シュードサーコスポラ菌による眼紋病、セプトリア菌による葉枯病又はふ枯病等のムギ類の病害;フザリウム菌による赤かび病、フィソデルマ菌による斑点病、プクシニア菌によるさび病、セトスフェリア菌によるすす紋病、コクリオボラス菌によるごま葉枯病、ピシウム菌による根腐病、ウスチラゴ菌による黒穂病等のトウモロコシの病害;ウスチラゴ菌による黒穂病、スタゴノスポラ菌による葉焼病、プクシニア菌によるさび病、ジベレラ菌による梢頭腐敗病、カルダリオミセス菌によるすす病、シュードサーコスポラ菌による葉枯病等のサトウキビの病害等のイネ科作物の病害;オイディウム菌によるうどんこ病、ファコプソラ菌によるさび病、ペロノスポラ菌によるべと病、フィトフトラ菌による疫病又は茎疫病、コレトトリカム菌による炭そ病、スクレロティニア菌による菌核病、ボトリティス菌による灰色かび病、フザリウム菌による根腐病又は立枯病等のマメ科作物の病害;フザリウム菌による萎黄病、ペロノスポラ菌又はヒアロペロノスポラ菌によるべと病、アルタナリア菌による黒斑病、フォーマ菌による根朽病、プラスモディオフォラ菌による根こぶ病、アファノミセス菌による根くびれ病、ピシウム菌によるピシウム腐敗病等のアブラナ科作物の病害;ブレミア菌によるべと病、フィトフトラ菌による疫病、ボトリティス菌による灰色かび病、スクレロティニア菌による菌核病、アエシジウム菌によるさび病等のキク科作物の病害;アルタナリア菌による輪紋病、フルビア菌による葉かび病、フィトフトラ菌による疫病又は灰色疫病、ボトリティス菌による灰色かび病、オイディウム菌によるうどんこ病、フザリウム菌による萎凋病、シュードサーコスポラ菌によるすすかび病等のトマトの病害;アルタナリア菌による夏疫病、フィトフトラ菌による疫病又は褐色腐敗病、スクレロティニア菌による菌核病、フザリウム菌による乾腐病等のバレイショの病害等のナス科作物の病害;コレトトリカム菌による炭そ病、スファエロテカ菌によるうどんこ病、ディディメラ菌によるつる枯病、シュードペロノスポラ菌によるべと病、フィトフトラ菌による疫病又は褐色腐敗病、コリネスポラ菌による褐斑病、フザリウム菌によるつる割病等のウリ科作物の病害;ペロノスポラ菌によるべと病、フィトフトラ菌による疫病、ボトリティス菌による灰色かび病、スクレロティニア菌による菌核病、プクシニア菌によるさび病等のヒガンバナ科ネギ属作物の病害;プラズモパラ菌によるべと病、アルタナリア菌による黒葉枯病又は黒斑病、ボトリティス菌による灰色かび病、スクレロティニア菌による菌核病、エリシフェ菌によるうどんこ病、サーコスポラ菌による斑点病等のセリ科作物の病害;ボトリティス菌による葉枯病、フィトフトラ菌による疫病、ホモプシス菌による茎枯病等のユリ科作物の病害;ペロノスポラ菌によるべと病、エリシフェ菌によるうどんこ病、リゾクトニア菌による立枯病等のタデ科作物の病害;アルブゴ菌による白さび病、フザリウム菌によるつる割病、セラトシスティス菌による黒斑病、ストレプトマイセス菌による立枯病等のヒルガオ科作物の病害;アファノミセス菌による根腐病、アルブゴ菌による白さび病、ペロノスポラ菌によるべと病、フィトフトラ菌による疫病、ボトリティス菌による灰色かび病、スクレロティニア菌による菌核病、オイディウム菌によるうどんこ病、サーコスポラ菌による褐斑病等のアカザ科作物の病害;エルシノエ菌による黒とう病、コレトトリカム菌による晩腐病、エリシフェ菌によるうどんこ病、プラズモパラ菌によるべと病、ボトリティス菌による灰色かび病、シュードサーコスポラ菌による褐斑病、ディアポルテ菌による枝膨病等のブドウ科作物の病害;スファエロテカ菌によるうどんこ病、ボトリティス菌による灰色かび病、グロメレラ菌による炭そ病、フザリウム菌による乾腐病等のイチゴの病害;モニリニア菌によるモニリア病、ポドスファエラ菌によるうどんこ病、アルタナリア菌による斑点落葉病、ヴェンチュリア菌による黒星病、グロメレラ菌による炭そ病、ディプロカーポン菌による褐斑病、ボトリオスファエリア菌による輪紋病、ジゴフィアラ菌によるすす点病、グロエオデス菌によるすす斑病、ミコスファエレラ菌による黒点病等のリンゴの病害;ヴェンチュリア菌による黒星病、アルタナリア菌による黒斑病、フィラクティニア菌によるうどんこ病、フィトフトラ菌による疫病、フザリウム菌による果実腐敗病等のナシ類の病害;モニリニア菌による灰星病、クラドスポリウム菌による黒星病、ホモプシス菌によるホモプシス腐敗病等のモモの病害等のバラ科作物の病害;ディアポルテ菌による黒点病、エルシノエ菌によるそうか病、フザリウム菌によるフザリウム立枯病等のカンキツの病害等のミカン科作物の病害;グロエオスポリウム菌による炭そ病、サーコスポラ菌による落葉病、フィラクティニア菌によるうどんこ病、ジゴフィアラ菌によるすす点病等のカキノキ科作物の病害;コレトトリカム菌による炭そ病、ペスタロオチオプシス菌による輪斑病、シュードモナス菌による赤焼病、エクソバシディウム菌によるもち病等のツバキ科作物の病害;ピシウム菌による根茎腐敗病等のショウガ科作物の病害;シュードペロノスポラ菌によるべと病等のアサ科作物の病害;ペロノスポラ菌によるべと病等シソ科作物の病害などの植物病害の防除に有効である。
Since compound (I) can control the various plant pathogenic fungi mentioned above, the present composition can preventatively or therapeutically control various diseases. In particular, this composition is effective against various diseases that are problematic in the field of agriculture and horticulture, such as seedling damping-off caused by Pythium, blast caused by Pyricularia, baka-nae caused by Fusarium, sesame leaf blight caused by Cochliobolus, and rhizoctonia. Rice diseases such as sheath blight; powdery mildew caused by Erysiphe bacteria, Fusarium head or crown rot caused by Fusarium fungi, rust caused by Puccinia fungi, brown snow rot caused by Pythium fungi, bare smut caused by Ustilago fungi, and pseudocirco Wheat diseases such as eye spot disease caused by Spora fungi, leaf blight or rot blight caused by Septoria fungi; Fusarium head blight caused by Fusarium fungi, leaf spot disease caused by Physoderma fungi, rust caused by Puccinia fungi, soot spot disease caused by Setosphaeria fungi, Diseases of corn such as sesame leaf blight caused by Cochliobolus fungi, root rot caused by Pythium fungi, and smut caused by Ustilago fungi; smut caused by Ustilago fungi, leaf scorch caused by Stagonospora fungi, puxinia fungi rust, and top rot caused by Gibberella fungi. Diseases of grass crops such as sugarcane diseases such as soot disease caused by Caldaromyces fungi and leaf blight caused by Pseudocercospora; powdery mildew caused by Oedium fungi, rust caused by Phacopsora fungi, and downy mildew caused by Peronospora fungi. Diseases of leguminous crops such as late blight or stem blight caused by Phytophthora fungi, anthracnose caused by Colletotrichum, sclerotia caused by Sclerotinia fungi, gray mold caused by Botrytis fungi, and root rot or damping-off caused by Fusarium fungi; yellowing disease caused by Fusarium fungi, downy mildew caused by Peronospora fungi or Hyaloperonospora fungi, black spot disease caused by Alternaria fungi, root rot disease caused by Forma fungi, clubroot disease caused by Plasmodiophora fungi, root necking disease caused by Aphanomyces fungi, Diseases of cruciferous crops such as Pythium rot caused by Pythium; downy mildew caused by Bremia, late blight caused by Phytophthora, gray mold caused by Botrytis, sclerotium caused by Sclerotinia, and rust caused by Aesidium. Diseases of family crops: ring spot caused by Alternaria, leaf mold caused by Fulvia, late blight or gray late blight caused by Phytophthora, gray mold caused by Botrytis, powdery mildew caused by Oedium, wilt caused by Fusarium, Pseudocircospora Tomato diseases such as sooty mold caused by fungi; diseases of potato such as summer blight caused by Alternaria fungi, late blight or brown rot caused by Phytophthora fungi, sclerotium disease caused by Sclerotinia fungi, and dry rot caused by Fusarium fungi, etc. Crop diseases: anthracnose caused by Colletotrichum, powdery mildew caused by Sphaeroteca, vine blight caused by Didymera, downy mildew caused by Pseudoperonospora, late blight or brown rot caused by Phytophthora, brown spot caused by Corynespora. Diseases of Cucurbitaceae crops such as vine split disease caused by Fusarium; downy mildew caused by Peronospora, late blight caused by Phytophthora, gray mold caused by Botrytis, sclerotia caused by Sclerotinia, and rust caused by Puccinia. Diseases of Allium genus crops in the Amaryllidaceae family; downy mildew caused by Plasmoparabacterium, black leaf blight or black spot caused by Alternaria fungi, gray mold caused by Botrytis fungus, sclerotium caused by Sclerotinia fungus, powdery mildew caused by Erysiphe fungus, Diseases of Umbelliferae crops such as spot disease caused by Circospora; Diseases of Liliaceae crops such as leaf blight caused by Botrytis, late blight caused by Phytophthora, and stem blight caused by Homopsis; downy mildew caused by Peronospora, and udon caused by Erysiphe. Diseases of Polygonaceae crops such as rotary fungus and damping-off caused by Rhizoctonia; white rust caused by Arbugobacterium, vine crack caused by Fusarium, black spot caused by Ceratocystis, damping-off caused by Streptomyces, etc. Diseases of crops in the Convolvulaceae family: Root rot caused by Aphanomyces, white rust caused by M. Arbugo, downy mildew caused by M. Peronospora, late blight caused by M. Phytophthora, gray mold caused by M. Botrytis, sclerotium caused by M. Sclerotinia, and M. Oidium. Diseases of Chenopodiaceae crops such as powdery mildew caused by Yersinoe bacterium, brown spot caused by Circospora bacterium; black rot caused by Yersinoe bacterium, late rot caused by Colletotrichum bacterium, powdery mildew caused by Erysiphe bacterium, downy mildew caused by Plasmoparabacterium, and Botrytis bacterium Diseases of grape family crops such as gray mold, brown spot caused by Pseudocercospora, and branch blight caused by Diaporte; powdery mildew caused by Sphaerotheca, gray mold caused by Botrytis, anthracnose caused by Glomerella, and Fusarium. Diseases of strawberries such as dry rot caused by Monilinia bacteria, powdery mildew caused by Podosphaera bacteria, leaf spot disease caused by Alternaria bacteria, scab caused by Venturia bacteria, anthracnose caused by Glomerella bacteria, and brown spot caused by Diplocarpon bacteria. Diseases of apples such as ring spot caused by Botryosphaeria, sooty spot caused by Digophiara, sooty spot caused by Gloeodes, and black spot caused by Mycosphaerella; scab caused by Venturia and black spot caused by Alternaria. Diseases of pears such as powdery mildew caused by Phylactinia fungi, late blight caused by Phytophthora fungi, and fruit rot caused by Fusarium fungi; gray blight caused by Monilinia fungi, black spot caused by Cladosporium fungi, homopsis rot caused by Homopsis fungi, etc. Diseases of Rosaceae crops such as peach diseases; Diseases of Rutaceae crops such as black spot caused by Diaporte fungi, scab caused by Yersinoe fungi, and citrus diseases such as Fusarium damping off caused by Fusarium fungi; Gloeosporium Diseases of persimmonaceous crops such as fungal anthracnose, leaf drop caused by Circospora, powdery mildew caused by Factinia, and sooty spot caused by Digophiala; anthracnose caused by Colletotrichum and ring spot caused by Pestaloothiopsis. Diseases of Camellia family crops such as red rot caused by Pseudomonas bacterium and blast disease caused by Exobasidium; diseases of Zingiberaceae crops such as rhizome rot caused by Pythium bacillus; It is effective in controlling plant diseases such as downy mildew caused by Peronospora and other diseases of Lamiaceae crops.
また、フザリウム菌による赤かび病又はクラウンロット病、コレトトリカム菌による炭そ病、チレチア菌によるなまぐさ黒穂病、ウスチラゴ菌による裸黒穂病、セファロスポリウム菌による条斑病、セプトリア菌によるふ枯病等のムギ類の病害;ビポラリス菌によるごま葉枯病、コレトトリカム菌による炭そ病、フザリウム菌による苗立枯病等のトウモロコシの病害;グロメレラ菌による赤腐病、セラトシスティス菌による黒腐病、スクレロスポラ菌によるべと病等のサトウキビの病害等のイネ科作物の病害;サーコスポラ菌による紫斑病、ペロノスポラ菌によるべと病、フザリウム菌による立枯病、セプトリア菌による褐紋病、ディアポルテ菌による黒点病、コレトトリカム菌による炭そ病、セプトグロエウム菌によるねむり病等のダイズの病害等のマメ科作物の病害;アルタナリア菌による黒斑病または黒すす病、ペロノスポラ菌によるべと病、シュードモナス菌による黒斑細菌病、ザントモナス菌による黒腐病、フォーマ菌による根朽病等のキャベツの病害;アルタナリア菌による黒斑病、フザリウム菌による萎黄病、ザントモナス菌による黒腐病等のダイコンの病害;アルタナリア菌による黒斑病、ザントモナス菌による黒腐病、バーティシリウム菌による黄化病等のハクサイの病害等のアブラナ科作物の病害;アルタナリア菌による輪紋病、クラビバクター菌によるかいよう病、ザントモナス菌による斑点細菌病等のトマトの病害;アルタナリア菌による褐斑病、ホモプシス菌による褐紋病等のナスの病害;ストレプトマイセス菌によるそうか病、ヘルミントスポリウム菌による銀か病、スポンゴスポラ菌による粉状そうか病等のバレイショの病害等ナス科作物の病害;アルタナリア菌による黒斑病、シュードモナス菌による斑点細菌病、ザントモナス菌による褐斑細菌病等のキュウリの病害等のウリ科作物の病害;アルタナリア菌による黒斑病、ボトリティス菌による灰色腐敗病又は菌糸性腐敗病、フザリウム菌による乾腐病、ペロノスポラ菌によるべと病、フィトフトラ菌による白色疫病又は茎疫病等のヒガンバナ科ネギ属作物の病害;アルタナリア菌による黒葉枯病又は黒斑病、ザントモナス菌による斑点細菌病等のニンジンの病害;セプトリア菌による葉枯病、スクレロティニア菌による菌核病、シュードモナス菌による葉枯細菌病等のセルリーの病害等のセリ科作物の病害;ペロノスポラ菌によるべと病、フザリウム菌による萎凋病、コレトトリカム菌による炭そ病等のホウレンソウの病害等のアカザ科作物の病害;などの種子伝染性病害にも有効である。
さらに、フザリウム菌、ピシウム菌、リゾクトニア菌、バーティシリウム菌、プラズモディオホーラ菌、チエラビオプシス菌などの植物病原菌によって引き起こされる土壌病害の防除にも有効である。 In addition, Fusarium fungus or crown rot disease, Colletotrichum fungus anthracnose, Tilletia fungus smut, Ustilago fungus streak disease, Cephalosporium bacterium streak disease, Septoria fungus blight, etc. Diseases of wheat such as sesame leaf blight caused by Bipolaris bacteria, anthracnose caused by Colletotrichum bacteria, and seedling damping off caused by Fusarium bacteria; red rot caused by Glomerella bacteria, black rot caused by Ceratocystis bacteria, Diseases of grass crops such as sugarcane diseases such as downy mildew caused by Sclerospora; purpura caused by Circospora, downy mildew caused by Peronospora, damping off caused by Fusarium, brown spot caused by Septoria, and Diaporte. Diseases of leguminous crops such as soybean diseases such as black spot, anthracnose caused by Colletotrichum, and downy mildew caused by Septogloeum; Diseases of cabbage such as bacterial spot, black rot caused by Xanthomonas fungi, root rot caused by Forma fungi; diseases of radish such as black spot caused by Alternaria fungus, yellow chlorosis caused by Fusarium fungus, black rot caused by Xanthomonas fungus; Diseases of cruciferous crops such as Chinese cabbage diseases such as black spot caused by Xanthomonas, black rot caused by Verticillium; ring spot caused by Alternaria, canker caused by Clavibacter, and canker caused by Xanthomonas. Diseases of tomatoes such as bacterial spot; Diseases of eggplant such as brown spot caused by Alternaria and brown spot caused by Homopsis; scab caused by Streptomyces, silver scab caused by Helmintosporium, and Spongospora. Diseases of solanaceous crops such as potato diseases such as powdery scab; diseases of cucurbitaceous crops such as black spot caused by Alternaria, bacterial spot caused by Pseudomonas, and bacterial brown spot caused by Xanthomonas. ; Black spot disease caused by Alternaria fungi, gray rot or mycelial rot caused by Botrytis fungi, dry rot caused by Fusarium fungi, downy mildew caused by Peronospora fungi, white blight or stem blight caused by Phytophthora fungi, etc. of crops of the Allium family Amaryllidaceae; Diseases: Carrot diseases such as black leaf blight or black spot caused by Alternaria fungi, and bacterial leaf spot caused by Xanthomonas bacteria; leaf blight caused by Septoria fungi, sclerotium caused by Sclerotinia bacteria, bacterial leaf blight caused by Pseudomonas bacteria, etc. Seed-borne diseases such as downy mildew caused by Peronospora, wilt caused by Fusarium, and diseases of spinach such as anthracnose caused by Colletotrichum; It is also effective for
Furthermore, it is also effective in controlling soil diseases caused by plant pathogenic bacteria such as Fusarium, Pythium, Rhizoctonia, Verticillium, Plasmodiophora, and Thielabiopsis.
さらに、フザリウム菌、ピシウム菌、リゾクトニア菌、バーティシリウム菌、プラズモディオホーラ菌、チエラビオプシス菌などの植物病原菌によって引き起こされる土壌病害の防除にも有効である。 In addition, Fusarium fungus or crown rot disease, Colletotrichum fungus anthracnose, Tilletia fungus smut, Ustilago fungus streak disease, Cephalosporium bacterium streak disease, Septoria fungus blight, etc. Diseases of wheat such as sesame leaf blight caused by Bipolaris bacteria, anthracnose caused by Colletotrichum bacteria, and seedling damping off caused by Fusarium bacteria; red rot caused by Glomerella bacteria, black rot caused by Ceratocystis bacteria, Diseases of grass crops such as sugarcane diseases such as downy mildew caused by Sclerospora; purpura caused by Circospora, downy mildew caused by Peronospora, damping off caused by Fusarium, brown spot caused by Septoria, and Diaporte. Diseases of leguminous crops such as soybean diseases such as black spot, anthracnose caused by Colletotrichum, and downy mildew caused by Septogloeum; Diseases of cabbage such as bacterial spot, black rot caused by Xanthomonas fungi, root rot caused by Forma fungi; diseases of radish such as black spot caused by Alternaria fungus, yellow chlorosis caused by Fusarium fungus, black rot caused by Xanthomonas fungus; Diseases of cruciferous crops such as Chinese cabbage diseases such as black spot caused by Xanthomonas, black rot caused by Verticillium; ring spot caused by Alternaria, canker caused by Clavibacter, and canker caused by Xanthomonas. Diseases of tomatoes such as bacterial spot; Diseases of eggplant such as brown spot caused by Alternaria and brown spot caused by Homopsis; scab caused by Streptomyces, silver scab caused by Helmintosporium, and Spongospora. Diseases of solanaceous crops such as potato diseases such as powdery scab; diseases of cucurbitaceous crops such as black spot caused by Alternaria, bacterial spot caused by Pseudomonas, and bacterial brown spot caused by Xanthomonas. ; Black spot disease caused by Alternaria fungi, gray rot or mycelial rot caused by Botrytis fungi, dry rot caused by Fusarium fungi, downy mildew caused by Peronospora fungi, white blight or stem blight caused by Phytophthora fungi, etc. of crops of the Allium family Amaryllidaceae; Diseases: Carrot diseases such as black leaf blight or black spot caused by Alternaria fungi, and bacterial leaf spot caused by Xanthomonas bacteria; leaf blight caused by Septoria fungi, sclerotium caused by Sclerotinia bacteria, bacterial leaf blight caused by Pseudomonas bacteria, etc. Seed-borne diseases such as downy mildew caused by Peronospora, wilt caused by Fusarium, and diseases of spinach such as anthracnose caused by Colletotrichum; It is also effective for
Furthermore, it is also effective in controlling soil diseases caused by plant pathogenic bacteria such as Fusarium, Pythium, Rhizoctonia, Verticillium, Plasmodiophora, and Thielabiopsis.
化合物(I)を植物に施用しても、施用された植物の外観的な変化(植物の黄化や葉枯れ等)は少ないので、化合物(I)が有効成分である本組成物は環境負荷が軽い特徴を有する。
さらに、化合物(I)は、優れた耐雨性、残効性、浸達性を有していることから、化合物(I)が有効成分である本組成物を植物体に施用することによって植物の地上部の有害菌類を一定の期間防除することができる。 Even when Compound (I) is applied to plants, there is little change in the appearance of the plants (yellowing, leaf withering, etc.), so this composition containing Compound (I) as an active ingredient has no environmental burden. has a light characteristic.
Furthermore, since Compound (I) has excellent rain resistance, residual effect, and penetrating properties, the present composition containing Compound (I) as an active ingredient can be applied to plants. Harmful fungi above ground can be controlled for a certain period of time.
さらに、化合物(I)は、優れた耐雨性、残効性、浸達性を有していることから、化合物(I)が有効成分である本組成物を植物体に施用することによって植物の地上部の有害菌類を一定の期間防除することができる。 Even when Compound (I) is applied to plants, there is little change in the appearance of the plants (yellowing, leaf withering, etc.), so this composition containing Compound (I) as an active ingredient has no environmental burden. has a light characteristic.
Furthermore, since Compound (I) has excellent rain resistance, residual effect, and penetrating properties, the present composition containing Compound (I) as an active ingredient can be applied to plants. Harmful fungi above ground can be controlled for a certain period of time.
種々の植物病害を防除するために、本組成物を植物体、植物病原菌又は土壌に施用することができる。
前記植物体とは、樹幹、茎、葉、花、果実のような植物の地上部、植物の種子、塊茎、根茎、根、実生、移植苗のような植物の地下部を意味する。
前記土壌とは、畑、水田、果樹園等の農耕地、及び芝生、森林等の非農耕地などの植物の栽培地を意味する。 In order to control various plant diseases, the present composition can be applied to plants, plant pathogens, or soil.
The plant body refers to above-ground parts of a plant such as a tree trunk, stem, leaves, flowers, and fruits, and underground parts of a plant such as seeds, tubers, rhizomes, roots, seedlings, and transplanted seedlings.
The soil refers to agricultural land such as fields, paddy fields, orchards, and non-agricultural land such as lawns and forests where plants are cultivated.
前記植物体とは、樹幹、茎、葉、花、果実のような植物の地上部、植物の種子、塊茎、根茎、根、実生、移植苗のような植物の地下部を意味する。
前記土壌とは、畑、水田、果樹園等の農耕地、及び芝生、森林等の非農耕地などの植物の栽培地を意味する。 In order to control various plant diseases, the present composition can be applied to plants, plant pathogens, or soil.
The plant body refers to above-ground parts of a plant such as a tree trunk, stem, leaves, flowers, and fruits, and underground parts of a plant such as seeds, tubers, rhizomes, roots, seedlings, and transplanted seedlings.
The soil refers to agricultural land such as fields, paddy fields, orchards, and non-agricultural land such as lawns and forests where plants are cultivated.
本組成物が施用される植物は農園芸上有用なものであれば特に制限は無いが、例えば、イネ科作物(イネ、コムギ、オオムギ、エンバク、ライムギ、トウモロコシ、サトウキビ等)、マメ科作物(ダイズ、インゲンマメ、アズキ、エンドウ、ラッカセイ、エダマメ、アルファルファ等)、アブラナ科作物(キャベツ、ハクサイ、ダイコン、カブ、ブロッコリー、カリフラワー、ナバナ、セイヨウアブラナ、ワサビ等)、キク科作物(レタス、ゴボウ、シュンギク、ヒマワリ等)、ナス科作物(バレイショ、ナス、トマト、ピーマン、タバコ、トウガラシ等)、ウリ科作物(キュウリ、カボチャ、メロン、スイカ、トウガン、ズッキーニ等)、ヒガンバナ科ネギ属作物(ネギ、ニラ、ラッキョウ、ニンニク、タマネギ、ワケギ等)、セリ科作物(セルリー、ニンジン、パセリ、ミツバ等)、ユリ科作物(ユリ、チューリップ、アスパラガス等)、タデ科作物(ソバ等)、ヒルガオ科作物(サツマイモ、エンサイ等)、アカザ科作物(ホウレンソウ、テンサイ等)、ブドウ科作物(ブドウ等)、バラ科作物(バラ、イチゴ、リンゴ、ナシ、モモ、ビワ、アーモンド等)、ミカン科作物(ミカン、レモン、オレンジ、カンキツ等)、カキノキ科作物(カキ等)、クワ科作物(イチジク等)、ツバキ科作物(チャ等)、モクセイ科作物(オリーブ、ジャスミン等)、アオイ科作物(ワタ、カカオ、オクラ等)、バショウ科作物(バナナ等)、ショウガ科作物(ショウガ、ミョウガ等)、アサ科作物(ホップ等)、シソ科作物(バジル等)、アカネ科作物(コーヒーノキ等)、パイナップル科作物(パイナップル、アナナス等)、イソマツ科作物(スターチス等)、ナデシコ科作物(カーネーション等)、スミレ科作物(パンジー等)が挙げられる。
The plants to which this composition is applied are not particularly limited as long as they are useful for agriculture and horticulture, but examples include grass crops (rice, wheat, barley, oats, rye, corn, sugarcane, etc.), leguminous crops ( soybean, kidney bean, adzuki bean, pea, groundnut, edamame, alfalfa, etc.), cruciferous crops (cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, napa, rapeseed, wasabi, etc.), Asteraceae crops (lettuce, burdock, Japanese chrysanthemum) , sunflowers, etc.), Solanaceae crops (potatoes, eggplants, tomatoes, green peppers, tobacco, chili peppers, etc.), Cucurbitaceae crops (cucumbers, pumpkins, melons, watermelons, chili peppers, zucchini, etc.), Amaryllidaceae crops (alliums, chives, etc.) , rakkyo, garlic, onion, scallion, etc.), Umbelliferae crops (celery, carrots, parsley, honeysuckle, etc.), Liliaceae crops (lilies, tulips, asparagus, etc.), Polygonaceae crops (buckwheat, etc.), Convolvulaceae crops ( Sweet potatoes, sugar beet, etc.), Chenopodiaceae crops (spinach, sugar beets, etc.), Vitaceae crops (grapes, etc.), Rosaceae crops (roses, strawberries, apples, pears, peaches, loquats, almonds, etc.), Rutaceae crops (mandarin oranges, Lemons, oranges, citrus, etc.), Persimmonaceae crops (persimmons, etc.), Moraceae crops (figs, etc.), Camellia family crops (cha, etc.), Oleaceae crops (olives, jasmine, etc.), Malvacaceae crops (cotton, cacao, etc.) okra, etc.), Musaceae crops (bananas, etc.), Zingiberaceae crops (ginger, ginger, etc.), Lamiaceae crops (hops, etc.), Lamiaceae crops (basil, etc.), Rubiaceae crops (coffee, etc.), Pineappleaceae crops ( Examples include pineapples, bromeliads, etc.), crops of the Lomoaceae family (statices, etc.), crops of the Caryophyllaceae family (carnations, etc.), and crops of the Viola family (pansies, etc.).
前記植物には、遺伝子組み換え技術や遺伝子編集技術を用いて育成された植物、例えば、環境ストレス耐性、除草剤耐性、害虫耐性、病害耐性などを付与された植物、または、成長、稔性形質、生産物の品質や収量などを改変された植物を含む。
The plants include plants grown using genetic recombination technology or gene editing technology, such as plants that have been endowed with environmental stress tolerance, herbicide tolerance, pest tolerance, disease tolerance, etc., or plants that have been endowed with growth, fertility traits, etc. Includes plants whose quality and yield have been modified.
本組成物は、通常、化合物(I)と補助剤とを混合して粉剤、粒剤、顆粒水和剤、水和剤、水性懸濁剤、油性懸濁剤、水溶剤、乳剤、液剤、ペースト剤、エアゾール剤、微量散布剤、マイクロカプセル剤などの種々の形態に製剤し使用されるが、本発明の目的に適合するかぎり、通常の当該分野に用いられているあらゆる製剤形態にすることができる。製剤に使用する前記補助剤としては、固体担体、液体担体が挙げられるが、必要に応じて、界面活性剤、その他の製剤用補助剤を添加することもできる。
前記固体担体の具体例としては、珪藻土、消石灰、炭酸カルシウム、タルク、ホワイトカーボン、カオリン、ベントナイト、カオリナイト、セリサイト、クレー、炭酸ナトリウム、重曹、芒硝、ゼオライト、澱粉、微粉シリカが挙げられる。
前記液体担体の具体例としては、水、トルエン、キシレン、ソルベントナフサ、ジオキサン、アセトン、イソホロン、メチルイソブチルケトン、クロロベンゼン、シクロヘキサン、ジメチルスルホキシド、N,N-ジメチルホルムアミド、ジメチルアセトアミド、N-メチル-2-ピロリドン、アルコールが挙げられる。
前記界面活性剤としては、脂肪酸塩、安息香酸塩、アルキルスルホコハク酸塩、ジアルキルスルホコハク酸塩、ポリカルボン酸塩、アルキル硫酸エステル塩、アルキル硫酸塩、アルキルアリール硫酸塩、アルキルジグリコールエーテル硫酸塩、アルコール硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アリールスルホン酸塩、リグニンスルホン酸塩、アルキルジフェニルエーテルジスルホン酸塩、ポリスチレンスルホン酸塩、アルキルリン酸エステル塩、アルキルアリールリン酸塩、スチリルアリールリン酸塩、ポリオキシエチレンアルキルエーテル硫酸エステル塩、ポリオキシエチレンアルキルアリールエーテルリン酸塩、ポリオキシエチレンアルキルアリールエーテル硫酸塩、ポリオキシエチレンアルキルアリールエーテル硫酸エステル塩、ポリオキシエチレンアルキルエーテルリン酸塩、ポリオキシエチレンアルキルアリールリン酸エステル塩、ナフタレンスルホン酸ホルマリン縮合物の塩のような陰イオン系の界面活性剤や展着剤;ソルビタン脂肪酸エステル、グリセリン脂肪酸エステル、脂肪酸ポリグリセライド、脂肪酸アルコールポリグリコールエーテル、アセチレングリコール、アセチレンアルコール、オキシアルキレンブロックポリマー、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンスチリルアリールエーテル、ポリオキシエチレングリコールアルキルエーテル、ポリエチレングリコール、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレングリセリン脂肪酸エステル、ポリオキシエチレン硬化ヒマシ油、ポリオキシプロピレン脂肪酸エステルのような非イオン系の界面活性剤や展着剤が挙げられる。
その他の製剤用補助剤の具体例としては、オリーブ油、カポック油、ひまし油、シュロ油、椿油、ヤシ油、ごま油、トウモロコシ油、米ぬか油、落花生油、綿実油、大豆油、菜種油、亜麻仁油、きり油、液状パラフィンなどの植物油や鉱物油;シリコーン;ザンサンガムなどが挙げられる。
これら補助剤の各成分は、本発明の目的から逸脱しないかぎり、1種又は2種以上を適宜選択して使用することができる。また、前記した補助剤以外にも当該分野で知られたものの中から適宜選んで使用することもでき、例えば、増量剤、増粘剤、沈降防止剤、凍結防止剤、分散安定剤、薬害軽減剤、防黴剤など通常使用される各種補助剤も使用することができる。化合物(I)と各種補助剤との配合割合は、重量比で、一般に0.001:99.999~95:5、望ましくは0.005:99.995~90:10である。これら製剤の実際の使用に際しては、そのまま使用するか、または水等の希釈剤を用いて所定濃度に希釈し、必要に応じて各種展着剤(界面活性剤、植物油、鉱物油など)を添加して使用することができる。 The present composition is usually prepared by mixing compound (I) and an adjuvant to form powders, granules, wettable powders, wettable powders, aqueous suspensions, oily suspensions, aqueous solutions, emulsions, solutions, etc. It can be formulated and used in various forms such as paste, aerosol, microspray, microcapsule, etc., but any formulation commonly used in the field may be used as long as it is compatible with the purpose of the present invention. Can be done. Examples of the auxiliary agents used in the formulation include solid carriers and liquid carriers, but surfactants and other formulation auxiliaries may also be added as necessary.
Specific examples of the solid carrier include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch, and finely divided silica.
Specific examples of the liquid carrier include water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N,N-dimethylformamide, dimethylacetamide, and N-methyl-2. - Examples include pyrrolidone and alcohol.
The surfactants include fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylate salts, alkyl sulfate ester salts, alkyl sulfates, alkylaryl sulfates, alkyl diglycol ether sulfates, Alcohol sulfate ester salt, alkyl sulfonate, alkylaryl sulfonate, aryl sulfonate, lignin sulfonate, alkyldiphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester salt, alkylaryl phosphate, styryl Aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether phosphate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate Anionic surfactants and spreading agents such as salts, polyoxyethylene alkylaryl phosphate ester salts, naphthalene sulfonic acid formalin condensates; sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polyesters; Glycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, Examples include nonionic surfactants and spreading agents such as polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, and polyoxypropylene fatty acid ester.
Specific examples of other formulation adjuvants include olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, and tung oil. , vegetable oil and mineral oil such as liquid paraffin; silicone; xanthan gum, and the like.
Each component of these auxiliary agents may be used alone or in combinations of two or more, as long as it does not depart from the purpose of the present invention. In addition to the above-mentioned auxiliary agents, those known in the field may be selected and used as appropriate, such as bulking agents, thickeners, anti-settling agents, anti-freezing agents, dispersion stabilizers, chemical damage reducers, etc. Various commonly used adjuvants such as antifungal agents and antifungal agents can also be used. The mixing ratio of compound (I) and various auxiliary agents is generally 0.001:99.999 to 95:5, preferably 0.005:99.995 to 90:10, by weight. When actually using these preparations, they can be used as is, or diluted to a specified concentration with a diluent such as water, and various spreading agents (surfactants, vegetable oil, mineral oil, etc.) may be added as necessary. and can be used.
前記固体担体の具体例としては、珪藻土、消石灰、炭酸カルシウム、タルク、ホワイトカーボン、カオリン、ベントナイト、カオリナイト、セリサイト、クレー、炭酸ナトリウム、重曹、芒硝、ゼオライト、澱粉、微粉シリカが挙げられる。
前記液体担体の具体例としては、水、トルエン、キシレン、ソルベントナフサ、ジオキサン、アセトン、イソホロン、メチルイソブチルケトン、クロロベンゼン、シクロヘキサン、ジメチルスルホキシド、N,N-ジメチルホルムアミド、ジメチルアセトアミド、N-メチル-2-ピロリドン、アルコールが挙げられる。
前記界面活性剤としては、脂肪酸塩、安息香酸塩、アルキルスルホコハク酸塩、ジアルキルスルホコハク酸塩、ポリカルボン酸塩、アルキル硫酸エステル塩、アルキル硫酸塩、アルキルアリール硫酸塩、アルキルジグリコールエーテル硫酸塩、アルコール硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アリールスルホン酸塩、リグニンスルホン酸塩、アルキルジフェニルエーテルジスルホン酸塩、ポリスチレンスルホン酸塩、アルキルリン酸エステル塩、アルキルアリールリン酸塩、スチリルアリールリン酸塩、ポリオキシエチレンアルキルエーテル硫酸エステル塩、ポリオキシエチレンアルキルアリールエーテルリン酸塩、ポリオキシエチレンアルキルアリールエーテル硫酸塩、ポリオキシエチレンアルキルアリールエーテル硫酸エステル塩、ポリオキシエチレンアルキルエーテルリン酸塩、ポリオキシエチレンアルキルアリールリン酸エステル塩、ナフタレンスルホン酸ホルマリン縮合物の塩のような陰イオン系の界面活性剤や展着剤;ソルビタン脂肪酸エステル、グリセリン脂肪酸エステル、脂肪酸ポリグリセライド、脂肪酸アルコールポリグリコールエーテル、アセチレングリコール、アセチレンアルコール、オキシアルキレンブロックポリマー、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンスチリルアリールエーテル、ポリオキシエチレングリコールアルキルエーテル、ポリエチレングリコール、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレングリセリン脂肪酸エステル、ポリオキシエチレン硬化ヒマシ油、ポリオキシプロピレン脂肪酸エステルのような非イオン系の界面活性剤や展着剤が挙げられる。
その他の製剤用補助剤の具体例としては、オリーブ油、カポック油、ひまし油、シュロ油、椿油、ヤシ油、ごま油、トウモロコシ油、米ぬか油、落花生油、綿実油、大豆油、菜種油、亜麻仁油、きり油、液状パラフィンなどの植物油や鉱物油;シリコーン;ザンサンガムなどが挙げられる。
これら補助剤の各成分は、本発明の目的から逸脱しないかぎり、1種又は2種以上を適宜選択して使用することができる。また、前記した補助剤以外にも当該分野で知られたものの中から適宜選んで使用することもでき、例えば、増量剤、増粘剤、沈降防止剤、凍結防止剤、分散安定剤、薬害軽減剤、防黴剤など通常使用される各種補助剤も使用することができる。化合物(I)と各種補助剤との配合割合は、重量比で、一般に0.001:99.999~95:5、望ましくは0.005:99.995~90:10である。これら製剤の実際の使用に際しては、そのまま使用するか、または水等の希釈剤を用いて所定濃度に希釈し、必要に応じて各種展着剤(界面活性剤、植物油、鉱物油など)を添加して使用することができる。 The present composition is usually prepared by mixing compound (I) and an adjuvant to form powders, granules, wettable powders, wettable powders, aqueous suspensions, oily suspensions, aqueous solutions, emulsions, solutions, etc. It can be formulated and used in various forms such as paste, aerosol, microspray, microcapsule, etc., but any formulation commonly used in the field may be used as long as it is compatible with the purpose of the present invention. Can be done. Examples of the auxiliary agents used in the formulation include solid carriers and liquid carriers, but surfactants and other formulation auxiliaries may also be added as necessary.
Specific examples of the solid carrier include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch, and finely divided silica.
Specific examples of the liquid carrier include water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N,N-dimethylformamide, dimethylacetamide, and N-methyl-2. - Examples include pyrrolidone and alcohol.
The surfactants include fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylate salts, alkyl sulfate ester salts, alkyl sulfates, alkylaryl sulfates, alkyl diglycol ether sulfates, Alcohol sulfate ester salt, alkyl sulfonate, alkylaryl sulfonate, aryl sulfonate, lignin sulfonate, alkyldiphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester salt, alkylaryl phosphate, styryl Aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether phosphate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate Anionic surfactants and spreading agents such as salts, polyoxyethylene alkylaryl phosphate ester salts, naphthalene sulfonic acid formalin condensates; sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polyesters; Glycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, Examples include nonionic surfactants and spreading agents such as polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, and polyoxypropylene fatty acid ester.
Specific examples of other formulation adjuvants include olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, and tung oil. , vegetable oil and mineral oil such as liquid paraffin; silicone; xanthan gum, and the like.
Each component of these auxiliary agents may be used alone or in combinations of two or more, as long as it does not depart from the purpose of the present invention. In addition to the above-mentioned auxiliary agents, those known in the field may be selected and used as appropriate, such as bulking agents, thickeners, anti-settling agents, anti-freezing agents, dispersion stabilizers, chemical damage reducers, etc. Various commonly used adjuvants such as antifungal agents and antifungal agents can also be used. The mixing ratio of compound (I) and various auxiliary agents is generally 0.001:99.999 to 95:5, preferably 0.005:99.995 to 90:10, by weight. When actually using these preparations, they can be used as is, or diluted to a specified concentration with a diluent such as water, and various spreading agents (surfactants, vegetable oil, mineral oil, etc.) may be added as necessary. and can be used.
本組成物の施用は、気象条件、製剤形態、対象作物、施用時期、施用場所、植物病害の種類や発生状況などの相違により一概に規定できないが、通常、一般に行なわれている施用方法、すなわち、散布処理、土壌処理、種子処理等により、本組成物又はその希釈物の施用を行うことができる。一般に行われている施用方法において、0.1~10,000ppm、望ましくは1~2000ppmの有効成分濃度で化合物(I)を施用することができる。一般に散布処理の場合、その施用適量としては、1ヘクタールあたり本組成物が、10~100,000g程度とすることができる。土壌処理の場合、その施用適量としては、1ヘクタールあたり本組成物が0.01~1,000g程度とすることができる。種子処理の場合、その施用適量としては、種子1kgあたり本組成物が0.001~100g、望ましくは0.01~1g程度とすることができる。
Although the application of the present composition cannot be absolutely defined due to differences in weather conditions, formulation form, target crop, application time, application location, type and occurrence of plant diseases, etc., it is usually possible to apply the composition by a commonly used application method, i.e. The present composition or a diluted product thereof can be applied by spraying, soil treatment, seed treatment, etc. In commonly practiced application methods, compound (I) can be applied at an active ingredient concentration of 0.1 to 10,000 ppm, preferably 1 to 2000 ppm. Generally, in the case of spraying treatment, the appropriate amount of the composition to be applied can be about 10 to 100,000 g per hectare. In the case of soil treatment, the appropriate amount of the composition to be applied can be about 0.01 to 1,000 g per hectare. In the case of seed treatment, the appropriate amount of the composition to be applied can be about 0.001 to 100 g, preferably about 0.01 to 1 g, per 1 kg of seeds.
前記散布処理とは、植物の樹幹、芽、茎葉、花、穂、果実の表面或いは植物病原菌に、本組成物の有効量を散布することにより、植物病原菌を防除する処理方法である。例えば、茎葉散布、樹幹散布等が挙げられる。
前記土壌処理とは、植物病原菌による被害から作物を保護するため、化合物(I)の有効量を植物の根部等から植物の内部に浸透移行させるために、土壌に本組成物を処理する方法である。例えば、潅注処理(本組成物を植物の栽培土壌に潅注する)、土壌混和処理(植物の栽培土壌と本組成物を混和する)、植穴処理、株元又は株間への処理(散布又は灌注)、培土、育苗箱、育苗トレイ、ペーパーポット又は苗床等に使用する土壌への混和処理等が挙げられる。
前記種子処理とは、植物病原菌による被害から作物を保護するため、作物の種子、球根等に直接或いは近傍に本組成物を処理することにより、植物病原菌を防除する処理方法である。例えば、塗布処理、粉衣処理、浸漬処理等が挙げられる。
その他、苗処理(灌注又は浸漬)、球根、塊茎、鱗茎、根等への浸漬処理、さらに、水耕栽培養液に混合するような水耕処理が挙げられる。処理は植物の全体であっても一部分(茎葉、芽、花、穂、果実、樹幹、種子、球根、塊茎、鱗茎、根等)であっても良い。 The above-mentioned spraying treatment is a treatment method for controlling plant pathogenic bacteria by spraying an effective amount of the present composition onto the surfaces of plant trunks, buds, stems, leaves, flowers, panicles, and fruits, or onto plant pathogenic bacteria. Examples include foliage spraying, tree trunk spraying, etc.
The above-mentioned soil treatment is a method of treating soil with the present composition in order to infiltrate and transfer an effective amount of compound (I) from the roots of the plant into the interior of the plant in order to protect crops from damage caused by plant pathogens. be. For example, irrigation treatment (drinking the present composition into the plant cultivation soil), soil mixing treatment (mixing the present composition with the plant cultivation soil), planting hole treatment, treatment at the base of the plant or between the plants (spraying or irrigation) ), mixing treatment with soil used for cultivation soil, seedling raising boxes, seedling raising trays, paper pots, seedling beds, etc.
The seed treatment is a treatment method for controlling plant pathogens by applying the present composition directly or in the vicinity of seeds, bulbs, etc. of crops in order to protect crops from damage caused by plant pathogens. Examples include coating treatment, powder coating treatment, dipping treatment, and the like.
Other examples include seedling treatment (irrigation or immersion), immersion treatment of bulbs, tubers, scales, roots, etc., and hydroponic treatment such as mixing with a hydroponic culture nutrient solution. The treatment may be on the whole plant or a part of the plant (foliage, buds, flowers, ears, fruits, trunks, seeds, bulbs, tubers, scales, roots, etc.).
前記土壌処理とは、植物病原菌による被害から作物を保護するため、化合物(I)の有効量を植物の根部等から植物の内部に浸透移行させるために、土壌に本組成物を処理する方法である。例えば、潅注処理(本組成物を植物の栽培土壌に潅注する)、土壌混和処理(植物の栽培土壌と本組成物を混和する)、植穴処理、株元又は株間への処理(散布又は灌注)、培土、育苗箱、育苗トレイ、ペーパーポット又は苗床等に使用する土壌への混和処理等が挙げられる。
前記種子処理とは、植物病原菌による被害から作物を保護するため、作物の種子、球根等に直接或いは近傍に本組成物を処理することにより、植物病原菌を防除する処理方法である。例えば、塗布処理、粉衣処理、浸漬処理等が挙げられる。
その他、苗処理(灌注又は浸漬)、球根、塊茎、鱗茎、根等への浸漬処理、さらに、水耕栽培養液に混合するような水耕処理が挙げられる。処理は植物の全体であっても一部分(茎葉、芽、花、穂、果実、樹幹、種子、球根、塊茎、鱗茎、根等)であっても良い。 The above-mentioned spraying treatment is a treatment method for controlling plant pathogenic bacteria by spraying an effective amount of the present composition onto the surfaces of plant trunks, buds, stems, leaves, flowers, panicles, and fruits, or onto plant pathogenic bacteria. Examples include foliage spraying, tree trunk spraying, etc.
The above-mentioned soil treatment is a method of treating soil with the present composition in order to infiltrate and transfer an effective amount of compound (I) from the roots of the plant into the interior of the plant in order to protect crops from damage caused by plant pathogens. be. For example, irrigation treatment (drinking the present composition into the plant cultivation soil), soil mixing treatment (mixing the present composition with the plant cultivation soil), planting hole treatment, treatment at the base of the plant or between the plants (spraying or irrigation) ), mixing treatment with soil used for cultivation soil, seedling raising boxes, seedling raising trays, paper pots, seedling beds, etc.
The seed treatment is a treatment method for controlling plant pathogens by applying the present composition directly or in the vicinity of seeds, bulbs, etc. of crops in order to protect crops from damage caused by plant pathogens. Examples include coating treatment, powder coating treatment, dipping treatment, and the like.
Other examples include seedling treatment (irrigation or immersion), immersion treatment of bulbs, tubers, scales, roots, etc., and hydroponic treatment such as mixing with a hydroponic culture nutrient solution. The treatment may be on the whole plant or a part of the plant (foliage, buds, flowers, ears, fruits, trunks, seeds, bulbs, tubers, scales, roots, etc.).
本組成物は、他の農園芸用薬剤、肥料、薬害軽減剤などから選ばれる他の成分と混用又は併用することができ、この場合に一層優れた効果、作用性を示すことがある。
前記混用又は併用とは、本組成物と他の成分とを、同時に、別々に又は時間間隔をおいて使用することを意味する。
他の農園芸用薬剤は、除草剤、殺虫剤、殺ダニ剤、殺線虫剤、殺土壌害虫剤、殺菌剤、抗ウイルス剤、誘引剤、抗生物質、植物ホルモン、植物成長調整剤などが挙げられる。特に、本組成物、並びに他の殺菌剤の有効成分化合物の1種又は2種以上と混用或いは併用した混合殺菌組成物は、適用範囲、薬剤処理の時期、防除活性等を好ましい方向へ改良することがある。尚、本組成物、並びに他の殺菌剤の有効成分化合物は、各々別々に製剤したものを散布時に混合して使用しても、両者を一緒に製剤して使用してもよい。本発明には、このような混合殺菌剤も含まれる。 The present composition can be mixed or used in combination with other ingredients selected from other agricultural and horticultural chemicals, fertilizers, phytotoxicity reducers, etc. In this case, even more excellent effects and actions may be exhibited.
The above-mentioned mixing or combination means using the present composition and other components simultaneously, separately, or at intervals of time.
Other agricultural and horticultural chemicals include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, and plant growth regulators. Can be mentioned. In particular, mixed fungicidal compositions that are used in combination with this composition and one or more active ingredient compounds of other fungicides improve the application range, timing of chemical treatment, pesticidal activity, etc. in a favorable direction. Sometimes. The active ingredient compounds of this composition and other fungicides may be prepared separately and mixed together at the time of spraying, or both may be prepared and used together. The present invention also includes such mixed fungicides.
前記混用又は併用とは、本組成物と他の成分とを、同時に、別々に又は時間間隔をおいて使用することを意味する。
他の農園芸用薬剤は、除草剤、殺虫剤、殺ダニ剤、殺線虫剤、殺土壌害虫剤、殺菌剤、抗ウイルス剤、誘引剤、抗生物質、植物ホルモン、植物成長調整剤などが挙げられる。特に、本組成物、並びに他の殺菌剤の有効成分化合物の1種又は2種以上と混用或いは併用した混合殺菌組成物は、適用範囲、薬剤処理の時期、防除活性等を好ましい方向へ改良することがある。尚、本組成物、並びに他の殺菌剤の有効成分化合物は、各々別々に製剤したものを散布時に混合して使用しても、両者を一緒に製剤して使用してもよい。本発明には、このような混合殺菌剤も含まれる。 The present composition can be mixed or used in combination with other ingredients selected from other agricultural and horticultural chemicals, fertilizers, phytotoxicity reducers, etc. In this case, even more excellent effects and actions may be exhibited.
The above-mentioned mixing or combination means using the present composition and other components simultaneously, separately, or at intervals of time.
Other agricultural and horticultural chemicals include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, and plant growth regulators. Can be mentioned. In particular, mixed fungicidal compositions that are used in combination with this composition and one or more active ingredient compounds of other fungicides improve the application range, timing of chemical treatment, pesticidal activity, etc. in a favorable direction. Sometimes. The active ingredient compounds of this composition and other fungicides may be prepared separately and mixed together at the time of spraying, or both may be prepared and used together. The present invention also includes such mixed fungicides.
化合物(I)、並びに他の殺菌剤の有効成分化合物との混合比は、気象条件、製剤形態、対象作物、施用時期、施用場所、植物病害の種類や発生状況、などの相違により一概に規定できないが、重量比で、一般に1:300~300:1、望ましくは1:100~100:1とすることができる。また、施用適量としては、1ヘクタール当りの総有効成分化合物量は0.1~70,000g、望ましくは1~30,000gとすることができる。本発明には、このような混合殺菌組成物の施用による植物病害の防除方法も含まれる。
The mixing ratio of Compound (I) and the active ingredient compounds of other fungicides is generally determined depending on differences in weather conditions, formulation form, target crop, application time, application location, type and occurrence of plant diseases, etc. However, the weight ratio can be generally 1:300 to 300:1, preferably 1:100 to 100:1. In addition, as for the appropriate application amount, the total amount of active ingredient compounds per hectare can be 0.1 to 70,000 g, preferably 1 to 30,000 g. The present invention also includes a method for controlling plant diseases by applying such a mixed fungicidal composition.
化合物(I)を含有する殺菌組成物の施用にあたっては、他の農園芸用薬剤、例えば殺菌剤、殺虫剤、殺ダニ剤、殺線虫剤、殺土壌害虫剤、抗ウイルス剤、誘引剤、除草剤、植物成長調整剤等をさらに併せて処理することもできる。
When applying the fungicidal composition containing compound (I), other agricultural and horticultural agents such as fungicides, insecticides, acaricides, nematicides, soil insecticides, antiviral agents, attractants, It is also possible to further treat with herbicides, plant growth regulators, etc.
上記他の農園芸用薬剤中の、殺菌剤の有効成分化合物(一般名)とは、例えば、下記の化合物群から適宜選択することができる。特に記載がない場合であっても、これら化合物に、塩、アルキルエステル、光学異性体のような各種構造異性体などが存在する場合は、当然それらも含まれる。
The active ingredient compound (common name) of the fungicide in the other agricultural and horticultural chemicals mentioned above can be appropriately selected, for example, from the following compound group. Even if there is no particular description, if salts, alkyl esters, various structural isomers such as optical isomers, etc. exist in these compounds, they are naturally included.
メパニピリム(mepanipyrim)、ピリメタニル(pyrimethanil)、シプロジニル(cyprodinil)のようなアニリノピリミジン系化合物;
アメトクトラジン(ametoctradin)のようなトリアゾロピリミジン系化合物;
トリシクラゾール(tricyclazole)のようなトリアゾロベンゾチアゾール系化合物;
フルアジナム(fluazinam)のようなピリジナミン系化合物;
トリアジメホン(triadimefon)、ビテルタノール(bitertanol)、トリフルミゾール(triflumizole)、エタコナゾール(etaconazole)、プロピコナゾール(propiconazole)、ペンコナゾール(penconazole)、フルシラゾール(flusilazole)、ミクロブタニル(myclobutanil)、シプロコナゾール(cyproconazole)、テブコナゾール(tebuconazole)、ヘキサコナゾール(hexaconazole)、フルコナゾール・シス(furconazole-cis)、プロクロラズ(prochloraz)、メトコナゾール(metconazole)、エポキシコナゾール(epoxiconazole)、テトラコナゾール(tetraconazole)、オキスポコナゾールフマル酸塩(oxpoconazole fumarate)、プロチオコナゾール(prothioconazole)、トリアジメノール(triadimenol)、フルトリアホール(flutriafol)、ジフェノコナゾール(difenoconazole)、フルキンコナゾール(fluquinconazole)、フェンブコナゾール(fenbuconazole)、ブロムコナゾール(bromuconazole)、ジニコナゾール(diniconazole)、シメコナゾール(simeconazole)、ペフラゾエート(pefurazoate)、イプコナゾール(ipconazole)、イミベンコナゾール(imibenconazole)、アザコナゾール(azaconazole)、トリチコナゾール(triticonazole)、イマザリル(imazalil)、イプフェントリフルコナゾール(ipfentrifluconazole)、メフェントリフルコナゾール(mefentrifluconazole)のようなアゾール系化合物;
キノメチオナート(chinomethionat)のようなキノキサリン系化合物;
マンネブ(maneb)、ジネブ(zineb)、マンゼブ(mancozeb)、ポリカーバメート(polycarbamate)、メチラム(metiram)、プロピネブ(propineb)、チラム(thiram)のようなジチオカーバメート系化合物;
フサライド(phthalide)、クロロタロニル(chlorothalonil)、キントゼン(quintozene)のような有機塩素系化合物;
ベノミル(benomyl)、チオファネートメチル(thiophanate-methyl)、カルベンダジム(carbendazim)、チアベンダゾール(thiabendazole)、フベリアゾール(fuberiazole)のようなイミダゾール系化合物;
シモキサニル(cymoxanil)のようなシアノアセトアミド系化合物;
メタラキシル(metalaxyl)、メタラキシル-M(metalaxyl-M;別名メフェノキサム(mefenoxam))、オキサジキシル(oxadixyl)、オフレース(ofurace)、ベナラキシル(benalaxyl)、ベナラキシル-M(benalaxyl-M、別名キララキシル(kiralaxyl、chiralaxyl))、フララキシル(furalaxyl)、バリフェナレート(valifenalate)のようなアシルアミノ酸系化合物;
シプロフラム(cyprofuram)、カルボキシン(carboxin)、オキシカルボキシン(oxycarboxin)、チフルザミド(thifluzamide)、ボスカリド(boscalid)、フェンヘキサミド(fenhexamid)、イソチアニル(isotianil)、チアジニル(tiadinil)、ピラジフルミド(pyraziflumid)のようなアニリド系化合物;
ジクロフルアニド(dichlofluanid)のようなスルファミド系化合物;
水酸化第二銅(cupric hydroxide)、有機銅(oxine copper)、無水硫酸銅、ノニルフェノールスルホン酸銅、8-ヒドロキシキノリン銅、ドデシルベンゼンスルホン酸ビスエチレンジアミン銅錯塩(II)(別名DBEDC)のような銅系化合物;
ホセチルアルミニウム(fosetyl-Al)、トルクロホスメチル(tolclofos-Methyl)、エジフェンホス(edifenphos)、イプロベンホス(iprobenfos)のような有機リン系化合物;
キャプタン(captan)、カプタホール(captafol)、フォルペット(folpet)のようなフタルイミド系化合物;
プロシミドン(procymidone)、イプロジオン(iprodione)、ビンクロゾリン(vinclozolin)のようなジカルボキシイミド系化合物;
フルトラニル(flutolanil)、メプロニル(mepronil)、ベノダニル(benodanil)、フルフェノキサジアザム(flufenoxadiazam)のようなベンズアニリド系化合物;
カルプロパミド(carpropamid)、ジクロシメット(diclocymet)、シルチオファム(silthiofam)、フェノキサニル(fenoxanil)のようなアミド系化合物;
ベンゾビンジフルピル(benzovindiflupyr)、ビキサフェン(bixafen)、フルーインダピル(fluindapyr)、フルキサピロキサド(fluxapyroxad)、フラメトピル(furametpyr)、イソピラザム(isopyrazam)、ペンフルフェン(penflufen)、ペンチオピラド(penthiopyrad)、ピジフルメトフェン(pydiflumetofen)、セダキサン(sedaxane)、イソフルーシプラム(isoflucypram)、インピルフルキサム(inpyrfluxam)、ピラプロポイン(pyrapropoyne)のようなピラゾールカルボキサミド系化合物;
フルオピコリド(fluopicolide)、フルオピラム(fluopyram)、ゾキサミド(zoxamide)、フルーオピモミド(fluopimomide)のようなベンズアミド系化合物;
フェンフラム(fenfuram)のようなフラニリド系化合物;
イソフェタミド(isofetamid)のようなチオフェンアミド系化合物;
トリホリン(triforine)のようなピペラジン系化合物;
ピリフェノックス(pyrifenox)、ピリソキサゾール(pyrisoxazole)、アミノピリフェン(aminopyrifen)のようなピリジン系化合物;
フェナリモル(fenarimol)、フェリムゾン(ferimzone)、ヌアリモール(nuarimol)、フルメチルスルホリム(flumetylsulforim)のようなピリミジン系化合物;
フェンプロピディン(fenpropidin)のようなピペリジン系化合物;
フェンプロピモルフ(fenpropimorph)、トリデモルフ(tridemorph)のようなモルホリン系化合物;
水酸化トリフェニルスズ(fentin hydroxide)、酢酸トリフェニルスズ(fentin acetate)のような有機スズ系化合物;
ペンシキュロン(pencycuron)のような尿素系化合物;
ジメトモルフ(dimethomorph)、フルモルフ(flumorph)、ピリモルフ(pyrimorph)、イプロバリカルブ(iprovalicarb)、ベンチアバリカルブ-イソプロピル(benthiavalicarb-isopropyl)、マンジプロパミド(mandipropamid)のようなカルボン酸アミド系化合物;
ジエトフェンカルブ(diethofencarb)のようなフェニルカーバメート系化合物;
フルジオキソニル(fludioxonil)、フェンピクロニル(fenpiclonil)のようなシアノピロール系化合物;
アゾキシストロビン(azoxystrobin)、クレソキシムメチル(kresoxim-methyl)、メトミノストロビン(metominostrobin)、トリフロキシストロビン(trifloxystrobin)、ピコキシストロビン(picoxystrobin)、オリザストロビン(oryzastrobin)、ジモキシストロビン(dimoxystrobin)、ピラクロストロビン(pyraclostrobin)、フルオキサストロビン(fluoxastrobin)、ピラオキシストロビン(Pyraoxystrobin)、ピラメトストロビン(Pyrametostrobin)、クモキシストロビン(coumoxystrobin)、エノキサストロビン(enoxastrobin)、フェナミンストロビン(fenaminstrobin)、フルフェノキシストロビン(flufenoxystrobin)、トリクロピリカルブ(triclopyricarb)、マンデストロビン(mandestrobin)のようなストロビルリン系化合物;
ファモキサドン(famoxadone)、オキサチアピプロリン(oxathiapiprolin)のようなオキサゾール系化合物;
エタボキサム(ethaboxam)のようなチアゾールカルボキサミド系化合物;
フェンアミドン(フェナミドン、fenamidone)のようなイミダゾリノン系化合物;
フルスルファミド(flusulfamide)のようなベンゼンスルホンアミド系化合物;
シフルフェナミド(cyflufenamid)のようなオキシムエーテル系化合物;
ジチアノン(dithianon)のようなアントラキノン系化合物;
メプチルジノカップ(meptyldinocap)のようなクロトン酸系化合物;
バリダマイシン(validamycin)、カスガマイシン(kasugamycin)、ストレプトマイシン(streptomycin)、ポリオキシン(polyoxins)のような抗生物質;
イミノクタジン(iminoctadine)、ドジン(dodine)、グアザチン(guazatine)のようなグアニジン系化合物;
ブチルアミン(butylamine)、セボクチラミン(seboctylamine)のような脂肪族窒素系化合物;
テブフロキン(tebufloquin)、キノキシフェン(quinoxyfen)、キノフメリン(quinofumelin)、イプフルフェノキン(ipflufenoquin)のようなキノリン系化合物;
フルチアニル(flutianil)のようなチアゾリジン系化合物;
プロパモカルブ塩酸塩(propamocarb hydrochloride)、ピリベンカルブ(pyribencarb)、トルプロカルブ(tolprocarb)のようなカーバメート系化合物;
ピカルブトラゾクス(picarbutrazox)、メチルテトラプロール(metyltetraprole)のようなテトラゾール系化合物;
アミスルブロム(amisulbrom)、シアゾファミド(cyazofamiid)のようなスルホンアミド系化合物;
メトラフェノン(metrafenone)、ピリオフェノン(pyriofenone)のようなアリルフェニルケトン系化合物;
プロベナゾール(probenazole)、ジクロベンチアゾクス(dichlobentiazox)のようなベンゾチアゾール系化合物;
フェンピラザミン(fenpyrazamine)のようなフェニルピラゾール系化合物;
イソプロチオラン(isoprothiolane)のようなジチオラン系化合物;
フェンピコキサミド(fenpicoxamid)、フロリルピコキサミド(florylpicoxamid)のようなピコリンアミド系化合物;
硫黄(Sulfur)、石灰硫黄剤のような硫黄系化合物;
その他の化合物として、ピロキロン(pyroquilon)、ジクロメジン(diclomezine)、クロルピクリン(chloropicrin)、ダゾメット(dazomet)、メタムナトリウム塩(metam-sodium)、プロキナジド(proquinazid)、スピロキサミン(spiroxamine)、ジピメチトロン(dipymetitrone)など;
Bacillus amyloliqefaciens strain QST713、Bacillus amyloliqefaciens strain FZB24、Bacillus amyloliqefaciens strain MBI600、Bacillus amyloliqefaciens strain D747、Pseudomonas fluorescens、Bacillus subtilis、Trichoderma atroviride SKT-1のような微生物殺菌剤;及び
ティーツリー油(Tea tree oil)のような植物抽出物。 Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil;
Triazolopyrimidine compounds such as ametoctradin;
Triazolobenzothiazole compounds such as tricyclazole;
Pyridinamine compounds such as fluazinam;
triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole , tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole oxpoconazole fumarate, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromco bromuconazole, diniconazole, simeconazole, pefurazoate, ipconazole, imibenconazole, azaconazole, triticonazole, imazalil, ipconazole Azole compounds such as ipfentrifluconazole, mefentrifluconazole;
Quinoxaline compounds such as chinomethionat;
Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram;
Organochlorine compounds such as phthalide, chlorothalonil, and quintozene;
Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole;
Cyanoacetamide compounds such as cymoxanil;
metalaxyl, metalaxyl-M (also known as mefenoxam), oxadixyl, ofurace, benalaxyl, benalaxyl-M, also known as chiralaxyl, chiralaxyl )), acylamino acid compounds such as furalaxyl, valifenalate;
Cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, fenhexamid, isotianil, tiadinil, pyraziflumid Anilide compounds such as;
Sulfamide compounds such as dichlofluanid;
Such as cupric hydroxide, oxine copper, anhydrous copper sulfate, copper nonylphenolsulfonate, copper 8-hydroxyquinoline, dodecylbenzenesulfonic acid bisethylenediamine copper complex (II) (also known as DBEDC). Copper-based compounds;
Organophosphorus compounds such as fosetyl-Al, tolclofos-Methyl, edifenphos, iprobenfos;
Phthalimide compounds such as captan, captafol, folpet;
Dicarboximide compounds such as procymidone, iprodione, vinclozolin;
Benzanilide compounds such as flutolanil, mepronil, benodanil, flufenoxadiazam;
Amides such as carpropamid, diclocymet, silthiofam, fenoxanil;
benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, pidiflu Pyrazole carboxamides such as pydiflumetofen, sedaxane, isoflucypram, inpyrfluxam, pyrapropoyne;
Benzamide compounds such as fluopicolide, fluopyram, zoxamide, fluopimomide;
Furanilide compounds such as fenfuram;
Thiophenamide compounds such as isofetamid;
piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox, pyrisoxazole, aminopyrifen;
Pyrimidine compounds such as fenarimol, ferimzone, nuarimol, flumetylsulforim;
piperidine compounds such as fenpropidin;
Morpholine compounds such as fenpropimorph and tridemorph;
Organotin compounds such as triphenyltin hydroxide and fentin acetate;
Urea-based compounds such as pencycuron;
Carboxylic acid amide compounds such as dimethomorph, flumorph, pyrimorph, iprovalicarb, benthiavalicarb-isopropyl, mandipropamid;
Phenyl carbamate compounds such as diethofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin ( dimoxystrobin), pyraclostrobin, fluoxastrobin, Pyraoxystrobin, Pyrametostrobin, coumoxystrobin, enoxastrobin, phenaminst Strobilurin compounds such as fenaminstrobin, flufenoxystrobin, triclopyricarb, mandestrobin;
Oxazole compounds such as famoxadone, oxathiapiprolin;
Thiazole carboxamides such as ethaboxam;
Imidazolinone compounds such as fenamidone;
Benzene sulfonamides such as flusulfamide;
Oxime ether compounds such as cyflufenamide;
Anthraquinone compounds such as dithianon;
Crotonic acid compounds such as meptyldinocap;
Antibiotics such as validamycin, kasugamycin, streptomycin, polyoxins;
Guanidine compounds such as iminoctadine, dodine, guazatine;
Aliphatic nitrogen compounds such as butylamine and seboctylamine;
quinoline compounds such as tebufloquin, quinoxyfen, quinofumelin, ipflufenoquin;
Thiazolidine compounds such as flutianil;
Carbamate compounds such as propamocarb hydrochloride, pyribencarb, tolprocarb;
Tetrazole compounds such as picarbutrazox, methyltetraprole;
Sulfonamide compounds such as amisulbrom, cyazofamiid;
Allyl phenyl ketone compounds such as metrafenone and pyriofenone;
Benzothiazole compounds such as probenazole, dichlobentiazox;
Phenylpyrazole compounds such as fenpyrazamine;
Dithiolane compounds such as isoprothiolane;
Picolinamide compounds such as fenpicoxamide, florylpicoxamide;
Sulfur-based compounds such as sulfur and lime sulfur agents;
Other compounds include pyroquilon, diclomezine, chloropicrin, dazomet, metam-sodium, proquinazid, spiroxamine, dipymetitrone, etc. ;
Microbial fungicides such as Bacillus amyloliqefaciens strain QST713, Bacillus amyloliqefaciens strain FZB24, Bacillus amyloliqefaciens strain MBI600, Bacillus amyloliqefaciens strain D747, Pseudomonas fluorescens, Bacillus subtilis, Trichoderma atroviride SKT-1; and Tea tree oil. Like plant extract.
アメトクトラジン(ametoctradin)のようなトリアゾロピリミジン系化合物;
トリシクラゾール(tricyclazole)のようなトリアゾロベンゾチアゾール系化合物;
フルアジナム(fluazinam)のようなピリジナミン系化合物;
トリアジメホン(triadimefon)、ビテルタノール(bitertanol)、トリフルミゾール(triflumizole)、エタコナゾール(etaconazole)、プロピコナゾール(propiconazole)、ペンコナゾール(penconazole)、フルシラゾール(flusilazole)、ミクロブタニル(myclobutanil)、シプロコナゾール(cyproconazole)、テブコナゾール(tebuconazole)、ヘキサコナゾール(hexaconazole)、フルコナゾール・シス(furconazole-cis)、プロクロラズ(prochloraz)、メトコナゾール(metconazole)、エポキシコナゾール(epoxiconazole)、テトラコナゾール(tetraconazole)、オキスポコナゾールフマル酸塩(oxpoconazole fumarate)、プロチオコナゾール(prothioconazole)、トリアジメノール(triadimenol)、フルトリアホール(flutriafol)、ジフェノコナゾール(difenoconazole)、フルキンコナゾール(fluquinconazole)、フェンブコナゾール(fenbuconazole)、ブロムコナゾール(bromuconazole)、ジニコナゾール(diniconazole)、シメコナゾール(simeconazole)、ペフラゾエート(pefurazoate)、イプコナゾール(ipconazole)、イミベンコナゾール(imibenconazole)、アザコナゾール(azaconazole)、トリチコナゾール(triticonazole)、イマザリル(imazalil)、イプフェントリフルコナゾール(ipfentrifluconazole)、メフェントリフルコナゾール(mefentrifluconazole)のようなアゾール系化合物;
キノメチオナート(chinomethionat)のようなキノキサリン系化合物;
マンネブ(maneb)、ジネブ(zineb)、マンゼブ(mancozeb)、ポリカーバメート(polycarbamate)、メチラム(metiram)、プロピネブ(propineb)、チラム(thiram)のようなジチオカーバメート系化合物;
フサライド(phthalide)、クロロタロニル(chlorothalonil)、キントゼン(quintozene)のような有機塩素系化合物;
ベノミル(benomyl)、チオファネートメチル(thiophanate-methyl)、カルベンダジム(carbendazim)、チアベンダゾール(thiabendazole)、フベリアゾール(fuberiazole)のようなイミダゾール系化合物;
シモキサニル(cymoxanil)のようなシアノアセトアミド系化合物;
メタラキシル(metalaxyl)、メタラキシル-M(metalaxyl-M;別名メフェノキサム(mefenoxam))、オキサジキシル(oxadixyl)、オフレース(ofurace)、ベナラキシル(benalaxyl)、ベナラキシル-M(benalaxyl-M、別名キララキシル(kiralaxyl、chiralaxyl))、フララキシル(furalaxyl)、バリフェナレート(valifenalate)のようなアシルアミノ酸系化合物;
シプロフラム(cyprofuram)、カルボキシン(carboxin)、オキシカルボキシン(oxycarboxin)、チフルザミド(thifluzamide)、ボスカリド(boscalid)、フェンヘキサミド(fenhexamid)、イソチアニル(isotianil)、チアジニル(tiadinil)、ピラジフルミド(pyraziflumid)のようなアニリド系化合物;
ジクロフルアニド(dichlofluanid)のようなスルファミド系化合物;
水酸化第二銅(cupric hydroxide)、有機銅(oxine copper)、無水硫酸銅、ノニルフェノールスルホン酸銅、8-ヒドロキシキノリン銅、ドデシルベンゼンスルホン酸ビスエチレンジアミン銅錯塩(II)(別名DBEDC)のような銅系化合物;
ホセチルアルミニウム(fosetyl-Al)、トルクロホスメチル(tolclofos-Methyl)、エジフェンホス(edifenphos)、イプロベンホス(iprobenfos)のような有機リン系化合物;
キャプタン(captan)、カプタホール(captafol)、フォルペット(folpet)のようなフタルイミド系化合物;
プロシミドン(procymidone)、イプロジオン(iprodione)、ビンクロゾリン(vinclozolin)のようなジカルボキシイミド系化合物;
フルトラニル(flutolanil)、メプロニル(mepronil)、ベノダニル(benodanil)、フルフェノキサジアザム(flufenoxadiazam)のようなベンズアニリド系化合物;
カルプロパミド(carpropamid)、ジクロシメット(diclocymet)、シルチオファム(silthiofam)、フェノキサニル(fenoxanil)のようなアミド系化合物;
ベンゾビンジフルピル(benzovindiflupyr)、ビキサフェン(bixafen)、フルーインダピル(fluindapyr)、フルキサピロキサド(fluxapyroxad)、フラメトピル(furametpyr)、イソピラザム(isopyrazam)、ペンフルフェン(penflufen)、ペンチオピラド(penthiopyrad)、ピジフルメトフェン(pydiflumetofen)、セダキサン(sedaxane)、イソフルーシプラム(isoflucypram)、インピルフルキサム(inpyrfluxam)、ピラプロポイン(pyrapropoyne)のようなピラゾールカルボキサミド系化合物;
フルオピコリド(fluopicolide)、フルオピラム(fluopyram)、ゾキサミド(zoxamide)、フルーオピモミド(fluopimomide)のようなベンズアミド系化合物;
フェンフラム(fenfuram)のようなフラニリド系化合物;
イソフェタミド(isofetamid)のようなチオフェンアミド系化合物;
トリホリン(triforine)のようなピペラジン系化合物;
ピリフェノックス(pyrifenox)、ピリソキサゾール(pyrisoxazole)、アミノピリフェン(aminopyrifen)のようなピリジン系化合物;
フェナリモル(fenarimol)、フェリムゾン(ferimzone)、ヌアリモール(nuarimol)、フルメチルスルホリム(flumetylsulforim)のようなピリミジン系化合物;
フェンプロピディン(fenpropidin)のようなピペリジン系化合物;
フェンプロピモルフ(fenpropimorph)、トリデモルフ(tridemorph)のようなモルホリン系化合物;
水酸化トリフェニルスズ(fentin hydroxide)、酢酸トリフェニルスズ(fentin acetate)のような有機スズ系化合物;
ペンシキュロン(pencycuron)のような尿素系化合物;
ジメトモルフ(dimethomorph)、フルモルフ(flumorph)、ピリモルフ(pyrimorph)、イプロバリカルブ(iprovalicarb)、ベンチアバリカルブ-イソプロピル(benthiavalicarb-isopropyl)、マンジプロパミド(mandipropamid)のようなカルボン酸アミド系化合物;
ジエトフェンカルブ(diethofencarb)のようなフェニルカーバメート系化合物;
フルジオキソニル(fludioxonil)、フェンピクロニル(fenpiclonil)のようなシアノピロール系化合物;
アゾキシストロビン(azoxystrobin)、クレソキシムメチル(kresoxim-methyl)、メトミノストロビン(metominostrobin)、トリフロキシストロビン(trifloxystrobin)、ピコキシストロビン(picoxystrobin)、オリザストロビン(oryzastrobin)、ジモキシストロビン(dimoxystrobin)、ピラクロストロビン(pyraclostrobin)、フルオキサストロビン(fluoxastrobin)、ピラオキシストロビン(Pyraoxystrobin)、ピラメトストロビン(Pyrametostrobin)、クモキシストロビン(coumoxystrobin)、エノキサストロビン(enoxastrobin)、フェナミンストロビン(fenaminstrobin)、フルフェノキシストロビン(flufenoxystrobin)、トリクロピリカルブ(triclopyricarb)、マンデストロビン(mandestrobin)のようなストロビルリン系化合物;
ファモキサドン(famoxadone)、オキサチアピプロリン(oxathiapiprolin)のようなオキサゾール系化合物;
エタボキサム(ethaboxam)のようなチアゾールカルボキサミド系化合物;
フェンアミドン(フェナミドン、fenamidone)のようなイミダゾリノン系化合物;
フルスルファミド(flusulfamide)のようなベンゼンスルホンアミド系化合物;
シフルフェナミド(cyflufenamid)のようなオキシムエーテル系化合物;
ジチアノン(dithianon)のようなアントラキノン系化合物;
メプチルジノカップ(meptyldinocap)のようなクロトン酸系化合物;
バリダマイシン(validamycin)、カスガマイシン(kasugamycin)、ストレプトマイシン(streptomycin)、ポリオキシン(polyoxins)のような抗生物質;
イミノクタジン(iminoctadine)、ドジン(dodine)、グアザチン(guazatine)のようなグアニジン系化合物;
ブチルアミン(butylamine)、セボクチラミン(seboctylamine)のような脂肪族窒素系化合物;
テブフロキン(tebufloquin)、キノキシフェン(quinoxyfen)、キノフメリン(quinofumelin)、イプフルフェノキン(ipflufenoquin)のようなキノリン系化合物;
フルチアニル(flutianil)のようなチアゾリジン系化合物;
プロパモカルブ塩酸塩(propamocarb hydrochloride)、ピリベンカルブ(pyribencarb)、トルプロカルブ(tolprocarb)のようなカーバメート系化合物;
ピカルブトラゾクス(picarbutrazox)、メチルテトラプロール(metyltetraprole)のようなテトラゾール系化合物;
アミスルブロム(amisulbrom)、シアゾファミド(cyazofamiid)のようなスルホンアミド系化合物;
メトラフェノン(metrafenone)、ピリオフェノン(pyriofenone)のようなアリルフェニルケトン系化合物;
プロベナゾール(probenazole)、ジクロベンチアゾクス(dichlobentiazox)のようなベンゾチアゾール系化合物;
フェンピラザミン(fenpyrazamine)のようなフェニルピラゾール系化合物;
イソプロチオラン(isoprothiolane)のようなジチオラン系化合物;
フェンピコキサミド(fenpicoxamid)、フロリルピコキサミド(florylpicoxamid)のようなピコリンアミド系化合物;
硫黄(Sulfur)、石灰硫黄剤のような硫黄系化合物;
その他の化合物として、ピロキロン(pyroquilon)、ジクロメジン(diclomezine)、クロルピクリン(chloropicrin)、ダゾメット(dazomet)、メタムナトリウム塩(metam-sodium)、プロキナジド(proquinazid)、スピロキサミン(spiroxamine)、ジピメチトロン(dipymetitrone)など;
Bacillus amyloliqefaciens strain QST713、Bacillus amyloliqefaciens strain FZB24、Bacillus amyloliqefaciens strain MBI600、Bacillus amyloliqefaciens strain D747、Pseudomonas fluorescens、Bacillus subtilis、Trichoderma atroviride SKT-1のような微生物殺菌剤;及び
ティーツリー油(Tea tree oil)のような植物抽出物。 Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil;
Triazolopyrimidine compounds such as ametoctradin;
Triazolobenzothiazole compounds such as tricyclazole;
Pyridinamine compounds such as fluazinam;
triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole , tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole oxpoconazole fumarate, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromco bromuconazole, diniconazole, simeconazole, pefurazoate, ipconazole, imibenconazole, azaconazole, triticonazole, imazalil, ipconazole Azole compounds such as ipfentrifluconazole, mefentrifluconazole;
Quinoxaline compounds such as chinomethionat;
Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram;
Organochlorine compounds such as phthalide, chlorothalonil, and quintozene;
Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole;
Cyanoacetamide compounds such as cymoxanil;
metalaxyl, metalaxyl-M (also known as mefenoxam), oxadixyl, ofurace, benalaxyl, benalaxyl-M, also known as chiralaxyl, chiralaxyl )), acylamino acid compounds such as furalaxyl, valifenalate;
Cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, fenhexamid, isotianil, tiadinil, pyraziflumid Anilide compounds such as;
Sulfamide compounds such as dichlofluanid;
Such as cupric hydroxide, oxine copper, anhydrous copper sulfate, copper nonylphenolsulfonate, copper 8-hydroxyquinoline, dodecylbenzenesulfonic acid bisethylenediamine copper complex (II) (also known as DBEDC). Copper-based compounds;
Organophosphorus compounds such as fosetyl-Al, tolclofos-Methyl, edifenphos, iprobenfos;
Phthalimide compounds such as captan, captafol, folpet;
Dicarboximide compounds such as procymidone, iprodione, vinclozolin;
Benzanilide compounds such as flutolanil, mepronil, benodanil, flufenoxadiazam;
Amides such as carpropamid, diclocymet, silthiofam, fenoxanil;
benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, pidiflu Pyrazole carboxamides such as pydiflumetofen, sedaxane, isoflucypram, inpyrfluxam, pyrapropoyne;
Benzamide compounds such as fluopicolide, fluopyram, zoxamide, fluopimomide;
Furanilide compounds such as fenfuram;
Thiophenamide compounds such as isofetamid;
piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox, pyrisoxazole, aminopyrifen;
Pyrimidine compounds such as fenarimol, ferimzone, nuarimol, flumetylsulforim;
piperidine compounds such as fenpropidin;
Morpholine compounds such as fenpropimorph and tridemorph;
Organotin compounds such as triphenyltin hydroxide and fentin acetate;
Urea-based compounds such as pencycuron;
Carboxylic acid amide compounds such as dimethomorph, flumorph, pyrimorph, iprovalicarb, benthiavalicarb-isopropyl, mandipropamid;
Phenyl carbamate compounds such as diethofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin ( dimoxystrobin), pyraclostrobin, fluoxastrobin, Pyraoxystrobin, Pyrametostrobin, coumoxystrobin, enoxastrobin, phenaminst Strobilurin compounds such as fenaminstrobin, flufenoxystrobin, triclopyricarb, mandestrobin;
Oxazole compounds such as famoxadone, oxathiapiprolin;
Thiazole carboxamides such as ethaboxam;
Imidazolinone compounds such as fenamidone;
Benzene sulfonamides such as flusulfamide;
Oxime ether compounds such as cyflufenamide;
Anthraquinone compounds such as dithianon;
Crotonic acid compounds such as meptyldinocap;
Antibiotics such as validamycin, kasugamycin, streptomycin, polyoxins;
Guanidine compounds such as iminoctadine, dodine, guazatine;
Aliphatic nitrogen compounds such as butylamine and seboctylamine;
quinoline compounds such as tebufloquin, quinoxyfen, quinofumelin, ipflufenoquin;
Thiazolidine compounds such as flutianil;
Carbamate compounds such as propamocarb hydrochloride, pyribencarb, tolprocarb;
Tetrazole compounds such as picarbutrazox, methyltetraprole;
Sulfonamide compounds such as amisulbrom, cyazofamiid;
Allyl phenyl ketone compounds such as metrafenone and pyriofenone;
Benzothiazole compounds such as probenazole, dichlobentiazox;
Phenylpyrazole compounds such as fenpyrazamine;
Dithiolane compounds such as isoprothiolane;
Picolinamide compounds such as fenpicoxamide, florylpicoxamide;
Sulfur-based compounds such as sulfur and lime sulfur agents;
Other compounds include pyroquilon, diclomezine, chloropicrin, dazomet, metam-sodium, proquinazid, spiroxamine, dipymetitrone, etc. ;
Microbial fungicides such as Bacillus amyloliqefaciens strain QST713, Bacillus amyloliqefaciens strain FZB24, Bacillus amyloliqefaciens strain MBI600, Bacillus amyloliqefaciens strain D747, Pseudomonas fluorescens, Bacillus subtilis, Trichoderma atroviride SKT-1; and Tea tree oil. Like plant extract.
上記他の農園芸用薬剤中の、殺虫剤、殺線虫剤、殺ダニ剤、又は殺土壌害虫剤の有効成分化合物(一般名)とは、例えば、下記の化合物群から適宜選択することができる。特に記載がない場合であっても、これら化合物に、塩、アルキルエステル、光学異性体のような各種構造異性体などが存在する場合は、当然それらも含まれる。
The active ingredient compound (common name) of the insecticide, nematicide, acaricide, or soil insecticide among the other agricultural and horticultural chemicals mentioned above may be appropriately selected from the following compound groups, for example. can. Even if there is no particular description, if salts, alkyl esters, various structural isomers such as optical isomers, etc. exist in these compounds, they are naturally included.
プロフェノホス(profenofos)、ジクロルボス(dichlorvos)、フェナミホス(fenamiphos)、フェニトロチオン(fenitrothion)、EPN((RS)-(O-ethyl O-4-nitrophenyl phenylphosphonothioate))、ダイアジノン(diazinon)、クロルピリホス(chlorpyrifos)、クロルピリホスメチル(chlorpyrifos-methyl)、アセフェート(acephate)、プロチオホス(prothiofos)、ホスチアゼート(fosthiazate)、カズサホス(cadusafos)、ジスルホトン(disulfoton)、イソキサチオン(isoxathion)、イソフェンホス(isofenphos)、エチオン(ethion)、エトリムホス(etrimfos)、キナルホス(quinalphos)、ジメチルビンホス(dimethylvinphos)、ジメトエート(dimethoate)、スルプロホス(sulprofos)、チオメトン(thiometon)、バミドチオン(vamidothion)、ピラクロホス(pyraclofos)、ピリダフェンチオン(pyridaphenthion)、ピリミホスメチル(pirimiphos-methyl)、プロパホス(propaphos)、ホサロン(phosalone)、ホルモチオン(formothion)、マラチオン(malathion)、テトラクロルビンホス(tetrachlorvinphos)、クロルフェンビンホス(chlorfenvinphos)、シアノホス(cyanophos)、トリクロルホン(trichlorfon)、メチダチオン(methidathion)、フェントエート(phenthoate)、オキシデプロホス(oxydeprofos、別名ESP)、アジンホスメチル(azinphos-methyl)、フェンチオン(fenthion)、ヘプテノホス(heptenophos)、パラチオン(parathion)、ホスホカルブ(phosphocarb)、デメトン-S-メチル(demeton-S-methyl)、モノクロトホス(monocrotophos)、メタミドホス(methamidophos)、イミシアホス(imicyafos)、パラチオン-メチル(parathion-methyl)、テルブホス(terbufos)、ホスファミドン(phosphamidon)、ホスメット(phosmet)、ホレート(phorate)のような有機リン酸エステル系化合物;
カルバリル(carbaryl)、プロポキスル(propoxur)、アルジカルブ(aldicarb)、カルボフラン(carbofuran)、チオジカルブ(thiodicarb)、メソミル(methomyl)、オキサミル(oxamyl)、エチオフェンカルブ(ethiofencarb)、ピリミカルブ(pirimicarb)、フェノブカルブ(fenobucarb)、カルボスルファン(carbosulfan)、ベンフラカルブ(benfuracarb)、ベンダイオカルブ(bendiocarb)、フラチオカルブ(furathiocarb)、イソプロカルブ(isoprocarb)、メトルカルブ(metolcarb)、キシリルカルブ(xylylcarb)、XMC(3,5-xylyl methylcarbamate)、フェノチオカルブ(fenothiocarb)のようなカーバメート系化合物;
カルタップ(cartap)、チオシクラム(thiocyclam)、シュウ酸水素チオシクラム(thiocyclam oxalate)、チオシクラム塩酸塩(thiocyclam hydrochloride)、ベンスルタップ(bensultap)、チオスルタップ(thiosultap)、モノスルタップ(monosultap;別名チオスルタップモノナトリウム(thiosultap-monosodium)、ビスルタップ(bisultap;別名チオスルタップジナトリウム(thiosultap-disodium)、ポリチアラン(polythialan)のようなネライストキシン誘導体;
ジコホル(dicofol)、テトラジホン(tetradifon)、エンドスルファン(endosulfan)、ジエノクロル(dienochlor)、ディルドリン(dieldrin)、メトキシクロル(methoxychlor)のような有機塩素系化合物;
酸化フェンブタスズ(fenbutatin oxide)、シヘキサチン(cyhexatin)のような有機金属系化合物;
フェンバレレート(fenvalerate)、ペルメトリン(permethrin)、シペルメトリン(cypermethrin)、アルファ-シペルメトリン(alpha-cypermethrin)、ゼータ-シペルメトリン(zeta-cypermethrin)、シータ-シペルメトリン(theta-cypermethrin)、ベータ-シペルメトリン(beta-cypermethrin)、デルタメトリン(deltamethrin)、シハロトリン(cyhalothrin)、ガンマ-シハロトリン(gamma-cyhalothrin)、ラムダ-シハロトリン(lambda-cyhalothrin)、テフルトリン(tefluthrin)、カッパ-テフルトリン(kappa-tefluthrin)、エトフェンプロックス(ethofenprox)、フルフェンプロックス(flufenprox)、シフルトリン(cyfluthrin)、ベータ-シフルトリン(beta-cyfluthrin)、フェンプロパトリン(fenpropathrin)、フルシトリネート(flucythrinate)、フルバリネート(fluvalinate)、シクロプロトリン(cycloprothrin)、ピレスリン(pyrethrins)、エスフェンバレレート(esfenvalerate)、テトラメスリン(tetramethrin)、レスメスリン(resmethrin)、プロトリフェンブト(protrifenbute)、ビフェントリン(bifenthrin)、カッパ-ビフェントリン(kappa-bifenthrin)、アクリナトリン(acrinathrin)、アレスリン(allethrin)、タウ-フルバリネート(tau-fluvalinate)、トラロメトリン(tralomethrin)、プロフルトリン(profluthrin)、メトフルトリン(metofluthrin)、イプシロンメトフルトリン(epsilon-metofluthrin)、ヘプタフルトリン(heptafluthrin)、フェノトリン(phenothrin)、フルメトリン(flumethrin)、モムフルオロトリン(momfluorothrin)、イプシロンモムフルオロトリン(epsilon-momfluorothrin)、シラフルオフェン(silafluofen)、クロロプラレトリン(chloroprallethrin)のようなピレスロイド系化合物;
ジフルベンズロン(diflubenzuron)、クロルフルアズロン(chlorfluazuron)、テフルベンズロン(teflubenzuron)、フルフェノクスロン(flufenoxuron)、ルフェヌロン(lufenuron)、ノバルロン(novaluron)、トリフルムロン(triflumuron)、ヘキサフルムロン(hexaflumuron)、ビストリフルロン(bistrifluron)、ノビフルムロン(noviflumuron)、フルアズロン(fluazuron)、フルフェノクスロン(flufenoxuron)のようなベンゾイルウレア系化合物;
メトプレン(methoprene)、ピリプロキシフェン(pyriproxyfen)、フェノキシカルブ(fenoxycarb)、ジオフェノラン(diofenolan)のような幼若ホルモン様化合物;
ピリダベン(pyridaben)のようなピリダジノン系化合物;
フェンピロキシメート(fenpyroximate)、フィプロニル(fipronil)、エチピロール(ethiprole)、アセトプロール(acetoprole)、ピラフルプロール(pyrafluprole)、ピリプロール(pyriprole)、シエノピラフェン(cyenopyrafen)、フルフィプロール(flufiprole)のようなピラゾール系化合物;
ピフルブミド(pyflubumide)、テブフェンピラド(tebufenpyrad)、トルフェンピラド(tolfenpyrad)、ジンプロピリダズ(dimpropyridaz)のようなピラゾールカルボキサミド系化合物;
クロラントラニリプロール(chlorantraniliprole)、シアントラニリプロール(cyantraniliprole)、シクラニリプロール(cyclaniliprole)、テトラニリプロール(tetraniliprole)、チクロピラゾフロル(tyclopyrazoflor)、フルクロルジニリプロール(fluchlordiniliprole)、チオラントラニリプロール(tiorantraniliprole)のようなピリジルピラゾール系化合物;
イミダクロプリド(imidacloprid)、ニテンピラム(nitenpyram)、アセタミプリド(acetamiprid)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)、クロチアニジン(clothianidin)、ニジノテフラン(nidinotefuran)、ジノテフラン(dinotefuran)、ニチアジン(nithiazine)のようなネオニコチノイド系化合物;
テブフェノジド(tebufenozide)、メトキシフェノジド(methoxyfenozide)、クロマフェノジド(chromafenozide)、ハロフェノジド(halofenozide)のようなヒドラジン系化合物;
ピリダリル(pyridalyl)、フロニカミド(flonicamid)のようなピリジン系化合物;
スピロジクロフェン(spirodiclofen)、スピロメシフェン(spiromesifen)、スピロブジフェン(spirobudifen)のようなテトロン酸系化合物;
スピロテトラマト(spirotetramat)、スピロピジオン(spiropidion)のようなテトラミン酸系化合物;
フルアクリピリム(fluacrypyrim)、ピリミノストロビン(pyriminostrobin)、フルピロキシストロビン(flupyroxystrobin)のようなストロビルリン系化合物;
フルフェネリム(flufenerim)、ピリミジフェン(pyrimidifen)のようなピリミジナミン系化合物;
マラチオン(malathion)のような有機硫黄化合物;
シロマジン(cyromazine)のようなトリアジン系化合物;
ヒドラメチルノン(hydramethylnon)のようなヒドラゾン系化合物;
フルベンジアミド(flubendiamide)、ブロフラニリド(broflanilide)、シハロジアミド(cyhalodiamide)のようなジアミド系化合物;
ジアフェンチウロン(diafenthiuron)、クロロメチウロン(chloromethiuron)のようなチオウレア系化合物;
アミトラズ(amitraz)、クロルジメホルム(chlordimeform)、クロロメブホルム(chloromebuform)のようなホルムアミジン系化合物;
ピメトロジン(pymetrozine)、ピリフルキナゾン(pyrifluquinazone)のようなピリジンアゾメチン系化合物;
アフォキソラネル(afoxolaner)、フルララネル(fluralaner)、フルキサメタミド(fluxametamide)、サロラネル(sarolaner)のようなイソキサゾリン系化合物;
また、その他の化合物として、ブプロフェジン(buprofezin)、ヘキシチアゾクス(hexythiazox)、トリアザメート(triazamate)、クロルフェナピル(chlorfenapyr)、インドキサカルブ(indoxacarb)、アセキノシル(acequinocyl)、エトキサゾール(etoxazole)、1,3-ジクロロプロペン(1,3-dichloropropene)、ベンクロチアズ(benclothiaz)、ビフェナゼート(bifenazate)、プロパルギット(propargite)、クロフェンテジン(clofentezine)、メタフルミゾン(metaflumizone)、シフルメトフェン(cyflumetofen)、フェナザキン(fenazaquin)、アミドフルメト(amidoflumet)、スルフルラミド(sulfluramid)、ヒドラメチルノン(hydramethylnon)、メタアルデヒド(metaldehyde)、スルホキサフロル(sulfoxaflor)、フルエンスルホン(fluensulfone)、ベルブチン(verbutin)、ジクロロメゾチアズ(dicloromezotiaz)、トリフルメゾピリム(triflumezopyrim)、フルヘキサホン(fluhexafon)、チオキサザフェン(tioxazafen)、アフィドピロペン(afidopyropen)、フロメトキン(flometoquin)、フルピラジフロン(flupyradifurone)、フルアザインドリジン(fluazaindolizine)、アシノナピル(acynonapyr)、ベンツピリモキサン(benzpyrimoxan)、フルーピリミン(flupyrimin)、オキサゾスルフィル(oxazosulfyl)のような化合物など。
また、本発明の組成物は下記化合物と組み合わせて施用してもよい。
Bacillus thuringiensis aizawai、Bacillus thuringiensis kurstaki、Bacillus thuringiensis israelensis、Bacillus thuringiensis japonensis、Bacillus thuringiensis tenebrionis又はBacillus thuringiensisが生成する結晶タンパク毒素、昆虫病原ウイルス剤、昆虫病原糸状菌剤、線虫病原糸状菌剤などのような微生物農薬;
アバメクチン(abamectin)、エマメクチン安息香酸塩(emamectin benzoate)、イベルメクチン(ivermectin)、ミルベメクチン(milbemectin)、ミルベマイシンオキシム(milbemycin oxime)、レピメクチン(lepimectin)、スピノサド(spinosad)、スピネトラム(spinetoram)のような抗生物質及び半合成抗生物質;
アザディラクチン(azadirachtin)、ロテノン(rotenone)、リアノジン(ryanodine)のような天然物;
ディート(deet)のような忌避剤;
パラフィン油、鉱物油(mineral oil)のような物理的防除剤;
レドプロナ(ledprona)のようなRNAi農薬。 profenofos, dichlorvos, fenamiphos, fenitrothion, EPN ((RS)-(O-ethyl O-4-nitrophenyl phenylphosphonothioate)), diazinon, chlorpyrifos, chlorpyrifos chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos ), quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl , propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion ), phenthoate, oxydeprofos (also known as ESP), azinphos-methyl, fenthion, heptenophos, parathion, phosphocarb, demeton-S-methyl ( demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet, phorate ) Organophosphate compounds such as;
carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, Carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC (3,5-xylyl methylcarbamate), phenothiocarb Carbamate compounds such as (fenothiocarb);
Cartap, thiocyclam, thiocyclam oxalate, thiocyclam hydrochloride, bensultap, thiosultap, monosultap; also known as thiosultap monosodium (thiosultap- Nelystoxin derivatives such as thiosultap-disodium, polythialan;
Organochlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor, dieldrin, methoxychlor;
Organometallic compounds such as fenbutatin oxide, cyhexatin;
Fenvalerate, permethrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, theta-cypermethrin, beta-cypermethrin Permethrin, deltamethrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, tefluthrin, kappa-tefluthrin, ethos fenprox, flufenprox, cyfluthrin, beta-cyfluthrin, fenpropathrin, flucythrinate, fluvalinate, cycloprothrin (cycloprothrin), pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, kappa-bifenthrin, acrinathrin ( acrinathrin, allethrin, tau-fluvalinate, tralomethrin, profluthrin, metofluthrin, epsilon-metofluthrin, heptafluthrin, Pyrethroid compounds such as phenothrin, flumethrin, momfluorothrin, epsilon-momfluorothrin, silafluofen, chloroprallethrin;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, bistrifluron Benzoylurea compounds such as (bistrifluron), noviflumuron, fluazuron, flufenoxuron;
Juvenile hormone-like compounds such as methoprene, pyriproxyfen, fenoxycarb, diofenolan;
Pyridazinone compounds such as pyridaben;
Pyrazole compounds such as fenpyroximate, fipronil, ethiprole, acetoprole, pyrafluprole, pyriprole, cyenopyrafen, flufiprole ;
Pyrazole carboxamides such as pyflubumide, tebufenpyrad, tolfenpyrad, and dimpropyridaz;
chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, tyclopyrazoflor, fluchlordiniliprole, thio Pyridylpyrazole compounds such as lantraniliprole;
Neonic drugs such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefuran, dinotefuran, nithiazine Noid compounds;
Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide;
Pyridine compounds such as pyridalyl and flonicamid;
Tetronic acid compounds such as spirodiclofen, spiromesifen, spirobudifen;
Tetramic acid compounds such as spirotetramat and spiropidion;
Strobilurin compounds such as fluacrypyrim, pyriminostrobin, flupyroxystrobin;
Pyrimidinamines such as flufenerim, pyrimidifen;
Organosulfur compounds such as malathion;
Triazine compounds such as cyromazine;
Hydrazone compounds such as hydramethylnon;
Diamide compounds such as flubendiamide, broflanilide, cyhalodiamide;
Thiourea compounds such as diafenthiuron and chloromethiuron;
Formamidine compounds such as amitraz, chlordimeform, chloromebuform;
Pyridine azomethine compounds such as pymetrozine and pyrifluquinazone;
isoxazoline compounds such as afoxolaner, fluralaner, fluxametamide, sarolaner;
Other compounds include buprofezin, hexythiazox, triazamate, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, 1,3-dichloropropene. (1,3-dichloropropene), benclothiaz, bifenazate, propargite, clofentezine, metaflumizone, cyflumetofen, fenazaquin, amidoflumet, sulfluramid, hydramethylnon, metaldehyde, sulfoxaflor, fluensulfone, verbutin, dicloromezotiaz, triflumezopyrim, fluhexafone (fluhexafon), thioxazafen (tioxazafen), afidopyropen (afidopyropen), flometoquin (flometoquin), flupyradifurone (flupyradifurone), fluazaindolizine (fluazaindolizine), acinonapyr (acynonapyr), benzpyrimoxan (benzpyrimoxan), flupyrimin, Compounds such as oxazosulfyl.
Moreover, the composition of the present invention may be applied in combination with the following compounds.
Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or crystal protein toxins produced by Bacillus thuringiensis, entomopathogenic viral agents, entomopathogenic fungal agents, nematode pathogenic fungal agents, etc. microbial pesticides;
Antibiotics like abamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin oxime, lepimectin, spinosad, spinetoram and semi-synthetic antibiotics;
Natural products such as azadirachtin, rotenone, ryanodine;
repellents such as DEET;
physical control agents such as paraffin oil, mineral oil;
RNAi pesticides like ledprona.
カルバリル(carbaryl)、プロポキスル(propoxur)、アルジカルブ(aldicarb)、カルボフラン(carbofuran)、チオジカルブ(thiodicarb)、メソミル(methomyl)、オキサミル(oxamyl)、エチオフェンカルブ(ethiofencarb)、ピリミカルブ(pirimicarb)、フェノブカルブ(fenobucarb)、カルボスルファン(carbosulfan)、ベンフラカルブ(benfuracarb)、ベンダイオカルブ(bendiocarb)、フラチオカルブ(furathiocarb)、イソプロカルブ(isoprocarb)、メトルカルブ(metolcarb)、キシリルカルブ(xylylcarb)、XMC(3,5-xylyl methylcarbamate)、フェノチオカルブ(fenothiocarb)のようなカーバメート系化合物;
カルタップ(cartap)、チオシクラム(thiocyclam)、シュウ酸水素チオシクラム(thiocyclam oxalate)、チオシクラム塩酸塩(thiocyclam hydrochloride)、ベンスルタップ(bensultap)、チオスルタップ(thiosultap)、モノスルタップ(monosultap;別名チオスルタップモノナトリウム(thiosultap-monosodium)、ビスルタップ(bisultap;別名チオスルタップジナトリウム(thiosultap-disodium)、ポリチアラン(polythialan)のようなネライストキシン誘導体;
ジコホル(dicofol)、テトラジホン(tetradifon)、エンドスルファン(endosulfan)、ジエノクロル(dienochlor)、ディルドリン(dieldrin)、メトキシクロル(methoxychlor)のような有機塩素系化合物;
酸化フェンブタスズ(fenbutatin oxide)、シヘキサチン(cyhexatin)のような有機金属系化合物;
フェンバレレート(fenvalerate)、ペルメトリン(permethrin)、シペルメトリン(cypermethrin)、アルファ-シペルメトリン(alpha-cypermethrin)、ゼータ-シペルメトリン(zeta-cypermethrin)、シータ-シペルメトリン(theta-cypermethrin)、ベータ-シペルメトリン(beta-cypermethrin)、デルタメトリン(deltamethrin)、シハロトリン(cyhalothrin)、ガンマ-シハロトリン(gamma-cyhalothrin)、ラムダ-シハロトリン(lambda-cyhalothrin)、テフルトリン(tefluthrin)、カッパ-テフルトリン(kappa-tefluthrin)、エトフェンプロックス(ethofenprox)、フルフェンプロックス(flufenprox)、シフルトリン(cyfluthrin)、ベータ-シフルトリン(beta-cyfluthrin)、フェンプロパトリン(fenpropathrin)、フルシトリネート(flucythrinate)、フルバリネート(fluvalinate)、シクロプロトリン(cycloprothrin)、ピレスリン(pyrethrins)、エスフェンバレレート(esfenvalerate)、テトラメスリン(tetramethrin)、レスメスリン(resmethrin)、プロトリフェンブト(protrifenbute)、ビフェントリン(bifenthrin)、カッパ-ビフェントリン(kappa-bifenthrin)、アクリナトリン(acrinathrin)、アレスリン(allethrin)、タウ-フルバリネート(tau-fluvalinate)、トラロメトリン(tralomethrin)、プロフルトリン(profluthrin)、メトフルトリン(metofluthrin)、イプシロンメトフルトリン(epsilon-metofluthrin)、ヘプタフルトリン(heptafluthrin)、フェノトリン(phenothrin)、フルメトリン(flumethrin)、モムフルオロトリン(momfluorothrin)、イプシロンモムフルオロトリン(epsilon-momfluorothrin)、シラフルオフェン(silafluofen)、クロロプラレトリン(chloroprallethrin)のようなピレスロイド系化合物;
ジフルベンズロン(diflubenzuron)、クロルフルアズロン(chlorfluazuron)、テフルベンズロン(teflubenzuron)、フルフェノクスロン(flufenoxuron)、ルフェヌロン(lufenuron)、ノバルロン(novaluron)、トリフルムロン(triflumuron)、ヘキサフルムロン(hexaflumuron)、ビストリフルロン(bistrifluron)、ノビフルムロン(noviflumuron)、フルアズロン(fluazuron)、フルフェノクスロン(flufenoxuron)のようなベンゾイルウレア系化合物;
メトプレン(methoprene)、ピリプロキシフェン(pyriproxyfen)、フェノキシカルブ(fenoxycarb)、ジオフェノラン(diofenolan)のような幼若ホルモン様化合物;
ピリダベン(pyridaben)のようなピリダジノン系化合物;
フェンピロキシメート(fenpyroximate)、フィプロニル(fipronil)、エチピロール(ethiprole)、アセトプロール(acetoprole)、ピラフルプロール(pyrafluprole)、ピリプロール(pyriprole)、シエノピラフェン(cyenopyrafen)、フルフィプロール(flufiprole)のようなピラゾール系化合物;
ピフルブミド(pyflubumide)、テブフェンピラド(tebufenpyrad)、トルフェンピラド(tolfenpyrad)、ジンプロピリダズ(dimpropyridaz)のようなピラゾールカルボキサミド系化合物;
クロラントラニリプロール(chlorantraniliprole)、シアントラニリプロール(cyantraniliprole)、シクラニリプロール(cyclaniliprole)、テトラニリプロール(tetraniliprole)、チクロピラゾフロル(tyclopyrazoflor)、フルクロルジニリプロール(fluchlordiniliprole)、チオラントラニリプロール(tiorantraniliprole)のようなピリジルピラゾール系化合物;
イミダクロプリド(imidacloprid)、ニテンピラム(nitenpyram)、アセタミプリド(acetamiprid)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)、クロチアニジン(clothianidin)、ニジノテフラン(nidinotefuran)、ジノテフラン(dinotefuran)、ニチアジン(nithiazine)のようなネオニコチノイド系化合物;
テブフェノジド(tebufenozide)、メトキシフェノジド(methoxyfenozide)、クロマフェノジド(chromafenozide)、ハロフェノジド(halofenozide)のようなヒドラジン系化合物;
ピリダリル(pyridalyl)、フロニカミド(flonicamid)のようなピリジン系化合物;
スピロジクロフェン(spirodiclofen)、スピロメシフェン(spiromesifen)、スピロブジフェン(spirobudifen)のようなテトロン酸系化合物;
スピロテトラマト(spirotetramat)、スピロピジオン(spiropidion)のようなテトラミン酸系化合物;
フルアクリピリム(fluacrypyrim)、ピリミノストロビン(pyriminostrobin)、フルピロキシストロビン(flupyroxystrobin)のようなストロビルリン系化合物;
フルフェネリム(flufenerim)、ピリミジフェン(pyrimidifen)のようなピリミジナミン系化合物;
マラチオン(malathion)のような有機硫黄化合物;
シロマジン(cyromazine)のようなトリアジン系化合物;
ヒドラメチルノン(hydramethylnon)のようなヒドラゾン系化合物;
フルベンジアミド(flubendiamide)、ブロフラニリド(broflanilide)、シハロジアミド(cyhalodiamide)のようなジアミド系化合物;
ジアフェンチウロン(diafenthiuron)、クロロメチウロン(chloromethiuron)のようなチオウレア系化合物;
アミトラズ(amitraz)、クロルジメホルム(chlordimeform)、クロロメブホルム(chloromebuform)のようなホルムアミジン系化合物;
ピメトロジン(pymetrozine)、ピリフルキナゾン(pyrifluquinazone)のようなピリジンアゾメチン系化合物;
アフォキソラネル(afoxolaner)、フルララネル(fluralaner)、フルキサメタミド(fluxametamide)、サロラネル(sarolaner)のようなイソキサゾリン系化合物;
また、その他の化合物として、ブプロフェジン(buprofezin)、ヘキシチアゾクス(hexythiazox)、トリアザメート(triazamate)、クロルフェナピル(chlorfenapyr)、インドキサカルブ(indoxacarb)、アセキノシル(acequinocyl)、エトキサゾール(etoxazole)、1,3-ジクロロプロペン(1,3-dichloropropene)、ベンクロチアズ(benclothiaz)、ビフェナゼート(bifenazate)、プロパルギット(propargite)、クロフェンテジン(clofentezine)、メタフルミゾン(metaflumizone)、シフルメトフェン(cyflumetofen)、フェナザキン(fenazaquin)、アミドフルメト(amidoflumet)、スルフルラミド(sulfluramid)、ヒドラメチルノン(hydramethylnon)、メタアルデヒド(metaldehyde)、スルホキサフロル(sulfoxaflor)、フルエンスルホン(fluensulfone)、ベルブチン(verbutin)、ジクロロメゾチアズ(dicloromezotiaz)、トリフルメゾピリム(triflumezopyrim)、フルヘキサホン(fluhexafon)、チオキサザフェン(tioxazafen)、アフィドピロペン(afidopyropen)、フロメトキン(flometoquin)、フルピラジフロン(flupyradifurone)、フルアザインドリジン(fluazaindolizine)、アシノナピル(acynonapyr)、ベンツピリモキサン(benzpyrimoxan)、フルーピリミン(flupyrimin)、オキサゾスルフィル(oxazosulfyl)のような化合物など。
また、本発明の組成物は下記化合物と組み合わせて施用してもよい。
Bacillus thuringiensis aizawai、Bacillus thuringiensis kurstaki、Bacillus thuringiensis israelensis、Bacillus thuringiensis japonensis、Bacillus thuringiensis tenebrionis又はBacillus thuringiensisが生成する結晶タンパク毒素、昆虫病原ウイルス剤、昆虫病原糸状菌剤、線虫病原糸状菌剤などのような微生物農薬;
アバメクチン(abamectin)、エマメクチン安息香酸塩(emamectin benzoate)、イベルメクチン(ivermectin)、ミルベメクチン(milbemectin)、ミルベマイシンオキシム(milbemycin oxime)、レピメクチン(lepimectin)、スピノサド(spinosad)、スピネトラム(spinetoram)のような抗生物質及び半合成抗生物質;
アザディラクチン(azadirachtin)、ロテノン(rotenone)、リアノジン(ryanodine)のような天然物;
ディート(deet)のような忌避剤;
パラフィン油、鉱物油(mineral oil)のような物理的防除剤;
レドプロナ(ledprona)のようなRNAi農薬。 profenofos, dichlorvos, fenamiphos, fenitrothion, EPN ((RS)-(O-ethyl O-4-nitrophenyl phenylphosphonothioate)), diazinon, chlorpyrifos, chlorpyrifos chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos ), quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl , propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion ), phenthoate, oxydeprofos (also known as ESP), azinphos-methyl, fenthion, heptenophos, parathion, phosphocarb, demeton-S-methyl ( demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet, phorate ) Organophosphate compounds such as;
carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, Carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC (3,5-xylyl methylcarbamate), phenothiocarb Carbamate compounds such as (fenothiocarb);
Cartap, thiocyclam, thiocyclam oxalate, thiocyclam hydrochloride, bensultap, thiosultap, monosultap; also known as thiosultap monosodium (thiosultap- Nelystoxin derivatives such as thiosultap-disodium, polythialan;
Organochlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor, dieldrin, methoxychlor;
Organometallic compounds such as fenbutatin oxide, cyhexatin;
Fenvalerate, permethrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, theta-cypermethrin, beta-cypermethrin Permethrin, deltamethrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, tefluthrin, kappa-tefluthrin, ethos fenprox, flufenprox, cyfluthrin, beta-cyfluthrin, fenpropathrin, flucythrinate, fluvalinate, cycloprothrin (cycloprothrin), pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, kappa-bifenthrin, acrinathrin ( acrinathrin, allethrin, tau-fluvalinate, tralomethrin, profluthrin, metofluthrin, epsilon-metofluthrin, heptafluthrin, Pyrethroid compounds such as phenothrin, flumethrin, momfluorothrin, epsilon-momfluorothrin, silafluofen, chloroprallethrin;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, bistrifluron Benzoylurea compounds such as (bistrifluron), noviflumuron, fluazuron, flufenoxuron;
Juvenile hormone-like compounds such as methoprene, pyriproxyfen, fenoxycarb, diofenolan;
Pyridazinone compounds such as pyridaben;
Pyrazole compounds such as fenpyroximate, fipronil, ethiprole, acetoprole, pyrafluprole, pyriprole, cyenopyrafen, flufiprole ;
Pyrazole carboxamides such as pyflubumide, tebufenpyrad, tolfenpyrad, and dimpropyridaz;
chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, tyclopyrazoflor, fluchlordiniliprole, thio Pyridylpyrazole compounds such as lantraniliprole;
Neonic drugs such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefuran, dinotefuran, nithiazine Noid compounds;
Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide;
Pyridine compounds such as pyridalyl and flonicamid;
Tetronic acid compounds such as spirodiclofen, spiromesifen, spirobudifen;
Tetramic acid compounds such as spirotetramat and spiropidion;
Strobilurin compounds such as fluacrypyrim, pyriminostrobin, flupyroxystrobin;
Pyrimidinamines such as flufenerim, pyrimidifen;
Organosulfur compounds such as malathion;
Triazine compounds such as cyromazine;
Hydrazone compounds such as hydramethylnon;
Diamide compounds such as flubendiamide, broflanilide, cyhalodiamide;
Thiourea compounds such as diafenthiuron and chloromethiuron;
Formamidine compounds such as amitraz, chlordimeform, chloromebuform;
Pyridine azomethine compounds such as pymetrozine and pyrifluquinazone;
isoxazoline compounds such as afoxolaner, fluralaner, fluxametamide, sarolaner;
Other compounds include buprofezin, hexythiazox, triazamate, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, 1,3-dichloropropene. (1,3-dichloropropene), benclothiaz, bifenazate, propargite, clofentezine, metaflumizone, cyflumetofen, fenazaquin, amidoflumet, sulfluramid, hydramethylnon, metaldehyde, sulfoxaflor, fluensulfone, verbutin, dicloromezotiaz, triflumezopyrim, fluhexafone (fluhexafon), thioxazafen (tioxazafen), afidopyropen (afidopyropen), flometoquin (flometoquin), flupyradifurone (flupyradifurone), fluazaindolizine (fluazaindolizine), acinonapyr (acynonapyr), benzpyrimoxan (benzpyrimoxan), flupyrimin, Compounds such as oxazosulfyl.
Moreover, the composition of the present invention may be applied in combination with the following compounds.
Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or crystal protein toxins produced by Bacillus thuringiensis, entomopathogenic viral agents, entomopathogenic fungal agents, nematode pathogenic fungal agents, etc. microbial pesticides;
Antibiotics like abamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin oxime, lepimectin, spinosad, spinetoram and semi-synthetic antibiotics;
Natural products such as azadirachtin, rotenone, ryanodine;
repellents such as DEET;
physical control agents such as paraffin oil, mineral oil;
RNAi pesticides like ledprona.
上記他の農園芸用薬剤中の、除草剤、抗ウイルス剤、誘引剤、抗生物質、植物ホルモン、植物成長調整剤の有効成分化合物(一般名)とは、例えば、下記の化合物群から適宜選択することができる。特に記載がない場合であっても、これら化合物に、塩、アルキルエステル、光学異性体のような各種構造異性体などが存在する場合は、当然それらも含まれる。
クロジナホッププロパルギル(clodinafop-propargyl)、クロホップ(clofop)、シハロホップブチル(cyhalofop-butyl)、ジクロホップメチル(diclofop-methyl)、フェノキサプロップエチル(fenoxaprop-ethyl)、フェンチアプロップ(fenthiaprop)、フルアジホップブチル(fluazifop-butyl)、ハロキシホップメチル(haloxyfop-methyl)、イソキサピリホップ(isoxapyrifop)、メタミホップ(metamifop)、キザロホップエチル(quizalofop-ethyl)のようなアリールオキシプロピオン酸エステル系化合物;
アロキシジム(alloxydim)、ブトロキシジム(butroxydim)、クレトジム(clethodim)、クロプロキシジム(cloproxydim)、シクロキシジム(cycloxydim)、プロホキシジム(profoxydim)、セトキシジム(sethoxydim)、テプラロキシジム(tepraloxydim)、トラルコキシジム(tralkoxydim)のようなシクロヘキサンジオン系化合物;
ピノキサデン(pinoxaden)のようなフェニルピラゾリン系化合物;
イマザメタベンズメチル(imazamethabenz-methyl)、イマザモックス(imazamox)、イマザピック(imazapic)、イマザピル(imazapyr)、イマザキン(imazaquin)、イマゼタピル(imazethapyr)のようなイミダゾリノン系化合物;
ビスピリバックナトリウム塩(bispyribac-sodium)、ピリベンゾキシム(pyribenzoxim)、ピリフタリド(pyriftalid)、ピリミノバックメチル(pyriminobac-methyl)、ピリチオバックナトリウム塩(pyrithiobac-sodium)のようなピリミジニルベンゾエート系化合物;
ピリミスルファン(pyrimisulfan)、トリアファモン(triafamone)のようなスルホンアニリド系化合物;
アミドスルフロン(amidosulfuron)、アジムスルフロン(azimsulfuron)、ベンスルフロンメチル(bensulfuron-methyl)、クロリムロンエチル(chlorimuron-ethyl)、クロルスルフロン(chlorsulfuron)、シノスルフロン(cinosulfuron)、シクロスルファムロン(cyclosulfamuron)、エタメトスルフロンメチル(ethametsulfuron-methyl)、エトキシスルフロン(ethoxysulfuron)、フラザスルフロン(flazasulfuron)、フルセトスルフロン(flucetosulfuron)、フルピルスルフロンメチルナトリウム塩(flupyrsulfuron-methyl-Na)、ホラムスルフロン(foramsulfuron)、ハロスルフロンメチル(halosulfuron-methyl)、イマゾスルフロン(imazosulfuron)、ヨードスルフロンメチルナトリウム塩(iodosulfuron-methyl-Na)、メソスルフロンメチル(mesosulfuron-methyl)、メタゾスルフロン(metazosulfuron)、メトスルフロンメチル(metsulfuron-methyl)、ニコスルフロン(nicosulfuron)、オルトスルファムロン(orthosulfamuron)、オキサスルフロン(oxasulfuron)、プリミスルフロンメチル(primisulfuron-methyl)、プロピリスルフロン(propyrisulfuron)、プロスルフロン(prosulfuron)、ピラゾスルフロンエチル(pyrazosulfuron-ethyl)、リムスルフロン(rimsulfuron)、スルホメツロンメチル(sulfometuron-methyl)、スルホスルフロン(sulfosulfuron)、チフェンスルフロンメチル(thifensulfuron-methyl)、トリアスルフロン(triasulfuron)、トリベニュロンメチル(tribenuron-methyl)、トリフロキシスルフロンナトリウム塩(trifloxysulfuron-Na)、トリフルスルフロンメチル(triflusulfuron-methyl)、トリトスルフロン(tritosulfuron)のようなスルホニルウレア系化合物;
フルカルバゾンナトリウム塩(flucarbazone-Na)、プロポキシカルバゾンナトリウム塩(propoxycarbazone-Na)、チエンカルバゾンメチル(thiencarbazone-methyl)のようなトリアゾリノン系化合物;
クロランスラムメチル(cloransulam-methyl)、ジクロスラム(diclosulam)、フロラスラム(florasulam)、フルメツラム(flumetsulam)、メトスラム(metosulam)、ペノキススラム(penoxsulam)、ピロクススラム(pyroxsulam)のようなトリアゾロピリミジン系化合物;
プロピザミド(propyzamide)、テブタム(tebutam)、イソキサベン(isoxaben)のようなベンズアミド系化合物;
クロルタールジメチル(chlorthal-dimethyl)、クロランベン(chloramben)、ジカンバ(dicamba)、TCBAのような安息香酸系化合物;
ベンフルラリン(benfluralin)、ブトルアリン(butralin)、ジニトラミン(dinitramine)、エタルフルラリン(ethalfluralin)、フルクロラリン(fluchloralin)、イソプロパリン(isopropalin)、ニトラリン(nitralin)、オリザリン(oryzalin)、ペンディメタリン(pendimethalin)、プロジアミン(prodiamine)、プロフルラリン(profluralin)、トリフルラリン(trifluralin)のようなジニトロアニリン系化合物;
ブタミホス(butamifos)、DMPAのようなホスホロアミデート系化合物;
ジチオピル(dithiopyr)、チアゾピル(thiazopyr)のようなピリジン系化合物;
2,4,5-T、2,4-D、2,4-DB、クロメプロップ(clomeprop)、ジクロルプロップ(dichlorprop)、フェノプロップ(fenoprop)、MCPA、MCPB、MCPPのようなフェノキシカルボン酸系化合物;
クロルフェナック(chlorfenac)、クロルフェンプロップ(chlorfenprop)のようなフェニルカルボン酸系化合物;
アミノピラリド(aminopyralid)、クロピラリド(clopyralid)、フロルピラウキシフェン(florpyrauxifen)、ハラウキシフェン(halauxifen)、ピクロラム(picloram)のようなピリジンカルボン酸系化合物;
フルロキシピル(fluroxypyr)、トリクロピル(triclopyr)のようなピリジルオキシカルボン酸系化合物;
アミノシクロピラクロル(aminocyclopyrachlor)のようなピリミジンカルボン酸系化合物;
キンクロラック(quinclorac)、キンメラック(quinmerac)のようなキノリンカルボン酸系化合物;
クロラノクリル(chloranocryl)、CMMP、DCPAのようなアミド系化合物;
クロルプロカルブ(chlorprocarb)、デスメディファム(desmedipham)、フェニソファム(phenisopham)、フェンメディファム(phenmedipham)のようなフェニルカーバメート系化合物;
ブロムピラゾン(brompyrazon)、クロリダゾン(chloridazon)のようなピリダジノン系化合物;
アメトリン(ametryne)、アトラトン(atraton)、アトラジン(atrazine)、アジプロトリン(aziprotryne)、クロラジン(chlorazine)、シアナジン(cyanazine)、シプラジン(cyprazine)、デスメトリン(desmetryne)、ジメタメトリン(dimethametryn)、ジプロペトリン(dipropetryn)、エグリナジンエチル(eglinazine-ethyl)、イパジン(ipazine)、メトプロトリン(methoprotryne)、プロシアジン(procyazine)、プログリナジン(proglinazine-ethyl)、プロメトン(prometon)、プロメトリン(prometryne)、プロパジン(propazine)、セブチラジン(sebuthylazine)、セクブメトン(secbumeton)、シマジン(simazine)、シメトリン(simetryne)、テルブメトン(terbumeton)、テルブチラジン(terbuthylazine)、テルブトリン(terbutryne)、トリエタジン(trietazine)のようなトリアジン系化合物;
エチオジン(ethiozin)、ヘキサジノン(hexazinone)、イソメチオジン(isomethiozin)、メタミトロン(metamitron)、メトリブジン(metribuzin)のようなトリアジノン系化合物;
アミカルバゾン(amicarbazone)のようなトリアゾリノン系化合物;
ブロマシル(bromacil)、イソシル(isocil)、レナシル(lenacil)、ターバシル(terbacil)のようなウラシル系化合物;
ベンズチアズロン(benzthiazuron)、ブロムロン(bromuron)、ブツロン(buturon)、クロルブロムロン(chlorbromuron)、クロロトルロン(chlorotoluron)、クロロクスロン(chloroxuron)、ジフェノキスロン(difenoxuron)、ジメフロン(dimefuron)、ジウロン(diuron)、エチジムロン(ethidimuron)、フェニュロン(fenuron)、フルオメツロン(fluometuron)、フルオチウロン(fluothiuron)、イソプロツロン(isoproturon)、イソウロン(isouron)、リニュロン(linuron)、メタベンズチアズロン(methabenzthiazuron)、メトベンズロン(metobenzuron)、メトブロムロン(metobromuron)、メトキスロン(metoxuron)、モノリニュロン(monolinuron)、モニュロン(monuron)、ネブロン(neburon)、パラフルロン(parafluron)、シデュロン(siduron)、テブチウロン(tebuthiuron)、チアザフルロン(thiazafluron)のようなウレア系化合物;
ベンタゾン(bentazon)のようなベンゾチアジアジノン系化合物;
ブロモフェノキシム(bromofenoxim)、ブロモキシニル(bromoxynil)、アイオキシニル(ioxynil)、クロルチアミド(chlorthiamid)、ジクロベニル(dichlobenil)のようなニトリル系化合物;
ピリデート(pyridate)のようなフェニルピリダジン系化合物;
グリホサート(glyphosate)のようなグリシン系化合物;
グルホシネートアンモニウム塩(glufosinate-ammonium)のようなホスフィン酸系化合物;
フルリドン(fluridone)、フルルタモン(flurtamone)のようなジフェニルヘテロ環系化合物;
フルロクロリドン(flurochloridone)、ノルフルラゾン(norflurazon)のようなN-フェニルヘテロ環系化合物;
ベフルブタミド(beflubutamid)、ベフルブタミド-M(beflubutamid-M)、ジフルフェニカン(diflufenican)、ピコリナフェン(picolinafen)のようなフェニルエーテル系化合物;
ビキスロゾン(bixlozone)、クロマゾン(clomazone)のようなイソオキサゾリジノン系化合物;
アシフルオルフェン(acifluorfen)、ビフェノックス(bifenox)、クロメトキシフェン(chlomethoxyfen)、クロルニトロフェン(chlornitrofen)、フルロジフェン(fluorodifen)、フルオログリコフェンエチル(fluoroglycofen-ethyl)、フルオロニトロフェン(fluoronitrofen)、ホメサフェン(fomesafen)、ラクトフェン(lactofen)、ニトロフェン(nitrofen)、オキシフローフェン(oxyfluorfen)のようなジフェニルエーテル系化合物;
ブタフェナシル(butafenacil)、クロルフタリム(chlorphthalim)、シニドンエチル(cinidon-ethyl)、フルミクロラックペンチル(flumiclorac-pentyl)、フルミオキサジン(flumioxazin)、フルミプロピン(flumipropyn)、フルチアセットメチル(fluthiacet-methyl)、ペントキサゾン(pentoxazone)、サフルフェナシル(saflufenacil)、チアフェナシル(tiafenacil)、トリフルジモキサジン(trifludimoxazin)のようなN-フェニルイミド系化合物;
オキサジアルギル(oxadiargyl)、オキサジアゾン(oxadiazon)のようなN-フェニルオキサジアゾロン系化合物;
アザフェニジン(azafenidin)、カルフェントラゾンエチル(carfentrazone-ethyl)、スルフェントラゾン(sulfentrazone)のようなN-フェニルトリアゾリノン系化合物;
ピラフルフェンエチル(pyraflufen-ethyl)のようなフェニルピラゾール系化合物;
カフェンストロール(cafenstrole)、フェントラザミド(fentrazamide)、イプフェンカルバゾン(ipfencarbazone)のようなアゾリルカルボキシアミド系化合物;
ベンフレセート(benfuresate)、エトフメセート(ethofumesate)のようなベンゾフラン系化合物;
フェノキサスルホン(fenoxasulfone)、ピロキサスルホン(pyroxasulfone)のようなイソキサゾリン系化合物;
インダノファン(indanofan)、トリジファン(tridiphane)のようなオキシラン系化合物;
ブチレート(butylate)、シクロエート(cycloate)、ジメピペレート(dimepiperate)、EPTC、エスプロカルブ(esprocarb)、モリネート(molinate)、オルベンカルブ(orbencarb)、ペブレート(pebulate)、プロスルホカルブ(prosulfocarb)、ベンチオカーブ(benthiocarb)、チオカルバジル(tiocarbazil)、トリアレート(tri-allate)、バーナレート(vernolate)のようなチオカーバメート系化合物;
アセトクロール(acetochlor)、アラクロール(alachlor)、アリドクロル(allidochlor)、ブタクロール(butachlor)、ブテナクロール(butenachlor)、デラクロール(delachlor)、ジエタチルエチル(diethatyl-ethyl)、ジメタクロール(dimethachlor)、ジメテナミド(dimethenamid)、メタザクロール(metazachlor)、メトラクロール(metolachlor)、ペトキサミド(pethoxamid)、プレチラクロール(pretilachlor)、プロパクロール(propachlor)、プロピソクロール(propisochlor)、プリナクロール(prynachlor)、テニルクロール(thenylchlor)のようなα-クロロアセトアミド系化合物;
フルフェナセット(flufenacet)、メフェナセット(mefenacet)のようなα-オキシアセトアミド系化合物;
アニロホス(anilofos)、ピペロホス(piperophos)のようなα-チオアセトアミド系化合物;
アシュラム(asulam)、バルバン(barban)、カルベタミド(carbetamide)、クロルブファム(chlorbufam)、クロルプロファム(chlorpropham)、プロファム(propham)、スエップ(swep)のようなカーバメート系化合物;
ジフルフェンゾピルナトリウム塩(diflufenzopyr-sodium)、ナプタラム(naptalam)のようなアリールカルボキシレート系化合物;
シペルコート(cyperquat)、ジクワット(diquat)、モルファムコート(morfamquat)、パラコート(paraquat)のようなピリジニウム系化合物;
ジノサム(dinosam)、ジノセブ(dinoseb)、ジノテルブ(dinoterb)、DNOC、エチノフェン(etinofen)、メジノテルブ(medinoterb)のようなジニトロフェノール系化合物;
イソキサフルトール(isoxaflutole)のようなイソオキサゾール系化合物;
ベンゾフェナップ(benzofenap)、ピラスルホトール(pyrasulfotole)、ピラゾリネート(pyrazolynate)、ピラゾキシフェン(pyrazoxyfen)、トルピラレート(tolpyralate)、トプラメゾン(topramezone)のようなピラゾール系化合物;
ビシクロピロン(bicyclopyrone)、フェンキノトリオン(fenquinotrione)、メソトリオン(mesotrione)、スルコトリオン(sulcotrione)、テフリルトリオン(tefuryltrione)、テンボトリオン(tembotrione)、ベンゾビシクロン(benzobicyclon)、ランコトリオン(lancotrione)のようなトリケトン系化合物;
インダジフラム(indaziflam)、トリアジフラム(triaziflam)のようなアルキルアジン系化合物;
フルポキサム(flupoxam)のようなトリアゾロカルボキサミド系化合物;
シンメチリン(cinmethylin)、メチオゾリン(methiozolin)のようなベンジルエーテル系化合物;
アクロニフェン(aclonifen)のようなジフェニルエーテル系化合物;
シクロピリモレート(cyclopyrimorate)のようなピリダジンジオン系化合物;
アミトロール(amitrole)のようなトリアゾール系化合物;
ジフェナミド(diphenamid)、ナプロアニリド(naproanilide)、ナプロパミド(napropamide)のようなアセトアミド系化合物;
フランプロップM(flamprop-m)のようなアリールアミノプロピオン酸系化合物;
ベンスリド(bensulide)のようなホスホロジチオエート系化合物;
ダラポン(dalapon)、フルプロパネート(flupropanate)、TCAのようなクロロ炭酸系化合物;
メフルイジド(mefluidide)、ペルフルイドン(perfluidone)のようなトリフルオロメタンスルホンアニリド系化合物;
その他の化合物として、ベナゾリンエチル(benazolin-ethyl)、ピラクロニル(pyraclonil)、エンドタール(endothal)、ブロモブチド(bromobutide)、クミルロン(cumyluron)、ジフェンゾコート(difenzoquat)、DSMA、ダイムロン(dymron)、エトベンザニド(etobenzanid)、ホサミン(fosamine)、メチルダイムロン(methyldymron)、モナリッド(monalide)、MSMA、オレイン酸(oleic acid)、オキサジクロメホン(oxaziclomefone)、ペラルゴン酸(pelargonic acid)、ピリブチカルブ(pyributicarb)、キノクラミン(quinoclamine)、テトフルピロリメト(tetflupyrolimet)、ジメスルファゼット(dimesulfazet)、エピリフェナシル(epyrifenacil)、トリピラスルホン(tripyrasulfone)、リミソキサフェン(rimisoxafen)、フェンピラゾン(fenpyrazone)、ジオキソピリトリオン(dioxopyritrione)、シピラフルオン(cypyrafluone)、ビピラゾン(bipyrazone)、ベンキトリオン(benquitrione)、フルクロラミノピル(fluchloraminopyr)、ピリフルベンゾキシム(pyriflubenzoxim)、フルフェノキシマシル(flufenoximacil)、イプトリアゾピリド(iptriazopyrid)、フルスルフィナム(flusulfinam)、ブロクロゾン(broclozone)、インドルオーキシピル(indolauxipyr)、ピラキネート(pyraquinate)、イカフォリン(icafolin)など; クロロインコナジド(chloroinconazide)、セボクチラミン(seboctylamine)のような抗ウイルス剤;
(Z)-11-ヘキサデセナール、((Z)-11-hexadecenal)、(Z)-11-ヘキサデセニルアセタート、((Z)-11-hexadecenyl acetate)、(Z)-11-テトラデセニルアセタート((Z)-11-tetradecenyl acetate)、(Z)-9-テトラデセニルアセタート((Z)-9-tetradecenyl acetate)、10-メチル-ドデシルアセタート(10-methyl-dodecyl acetate)、(Z)-9-ドデセニルアセタート((Z)-9-dodecenyl acetate)、11-ドデセニルアセタート(11-dodecenyl acetate)、(Z)-11-テトラデセン-1-オール((Z)-11-tetradecen-1-ol)、リトルア(litlure)、(Z,E)-9,11-テトラデカジエニルアセタート((Z,E)-9,11-tetradecadienyl acetate)、(Z)-9,12-テトラデカジエニルアセタート((Z)-9,12-tetradecadienyl acetate)、(Z)-9-テトラデセン-1-オール((Z)-9-tetradecen-1-ol)のような誘引剤;
ビアラホス(bialaphos)のような抗生物質;
インドール-3-酢酸(indol-3-acetic acid)、ジベレリン(gibberellin)、ゼアチン(zeatin)、カイネチン(kinetin)、アブシジン酸(abscisic acid)、エチレン(ethylene)、ブラシノステロイド(brassinosteroid)、ジャスモン酸類(jasmonate)、ストリゴラクトン(strigolactone)のような植物ホルモン;
4-クロロフェノキシ酢酸(4-chlorophenoxyacetic acid)、1-ナフチルアセトアミド(1-naphthylacetamide)、プロヒドロジャスモン(prohydrojasmon)、アビグリシン(aviglycine)、1-メチルシクロプロペン(1-methylcyclopropene)、エテホン(ethephon)のような植物成長調整剤。 The active ingredient compounds (common names) of herbicides, antiviral agents, attractants, antibiotics, plant hormones, and plant growth regulators among the other agricultural and horticultural chemicals mentioned above are, for example, appropriately selected from the following compound groups. can do. Even if there is no particular description, if salts, alkyl esters, various structural isomers such as optical isomers, etc. exist in these compounds, they are naturally included.
clodinafop-propargyl, clofop, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenthiaprop , aryloxypropionic acids such as fluazifop-butyl, haloxyfop-methyl, isoxapyrifop, metamifop, quizalofop-ethyl Ester compounds;
Like alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim cyclohexanedione-based compounds;
Phenylpyrazoline compounds such as pinoxaden;
imidazolinone compounds such as imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
Pyrimidinyl benzoate compounds such as bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium;
Sulfonanilide compounds such as pyrimisulfan and triafamone;
amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron ), ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron-methyl-Na, foramsulfuron (foramsulfuron), halosulfuron-methyl, imazosulfuron (imazosulfuron), iodosulfuron-methyl-Na, mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl ( metsulfuron-methyl), nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyra pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribe Sulfonylurea compounds such as tribenuron-methyl, trifloxysulfuron-Na, triflusulfuron-methyl, tritosulfuron;
Triazolinones such as flucarbazone-Na, propoxycarbazone-Na, and thiencarbazone-methyl;
triazolopyrimidine compounds such as chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, pyroxsulam;
Benzamide compounds such as propyzamide, tebutam, isoxaben;
Benzoic acid compounds such as chlorthal-dimethyl, chloramben, dicamba, TCBA;
benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, nitralin, oryzalin, pendimethalin, Dinitroaniline compounds such as prodiamine, profluralin, trifluralin;
Phosphoramidate compounds such as butamifos, DMPA;
Pyridine compounds such as dithiopyr and thiazopyr;
Phenoxycarboxylic acids such as 2,4,5-T, 2,4-D, 2,4-DB, clomeprop, dichlorprop, fenoprop, MCPA, MCPB, MCPP Compound;
Phenylcarboxylic acid compounds such as chlorfenac and chlorfenprop;
Pyridine carboxylic acid compounds such as aminopyralid, clopyralid, florpyrauxifen, halauxifen, picloram;
Pyridyloxycarboxylic acid compounds such as fluroxypyr and triclopyr;
Pyrimidine carboxylic acid compounds such as aminocyclopyrachlor;
quinoline carboxylic acid compounds such as quinclorac and quinmerac;
Amide compounds such as chloranocryl, CMMP, DCPA;
Phenyl carbamate compounds such as chlorprocarb, desmedipham, phenisopham, phenmedipham;
Pyridazinone compounds such as brompyrazon and chloridazon;
ametrine, atraton, atrazine, aziprotryne, chlorazine, cyanazine, cyprazine, desmetrine, dimethametryn, dipropetryn , eglinazine-ethyl, ipazine, methoprotryne, procyazine, proglinazine-ethyl, prometon, prometryne, propazine, sebutylazine ( triazine compounds such as sebuthylazine, secbumeton, simazine, simetryne, terbumeton, terbuthylazine, terbutryne, trietazine;
triazinones such as ethiozin, hexazinone, isomethiozin, metamitron, metribuzin;
Triazolinone compounds such as amicarbazone;
Uracil compounds such as bromacil, isocil, lenacil, terbacil;
benzthiazuron, bromuron, buturon, chlorbromuron, chlorotoluron, chloroxuron, difenoxuron, dimefuron, diuron, ethidimuron (ethidimuron), fenuron, fluometuron, fluothiuron, isoproturon, isouron, linuron, methabenzthiazuron, metobenzuron, methobromuron ( urea compounds such as metobromuron, metoxuron, monolinuron, monuron, neburon, parafluron, siduron, tebuthiuron, thiazafluron;
Benzothiadiazinone compounds such as bentazon;
Nitriles such as bromofenoxim, bromoxynil, ioxynil, chlorthiamide, dichlobenil;
Phenylpyridazine compounds such as pyridate;
Glycine-based compounds such as glyphosate;
Phosphinic acid compounds such as glufosinate-ammonium;
Diphenyl heterocyclic compounds such as fluridone, flurtamone;
N-phenyl heterocyclic compounds such as flurochloridone, norflurazon;
Phenyl ether compounds such as beflubutamide, beflubutamid-M, diflufenican, picolinafen;
Isoxazolidinone compounds such as bixlozone and clomazone;
acifluorfen, bifenox, chlomethoxyfen, chlornitrofen, fluorodifen, fluoroglycofen-ethyl, fluoronitrofen, fomesafen, Diphenyl ether compounds such as lactofen, nitrofen, oxyfluorfen;
butafenacil, chlorphthalim, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, fluthiacet-methyl, pentoxazone ), N-phenylimide compounds such as saflufenacil, tiafenacil, trifludimoxazine;
N-phenyloxadiazolone compounds such as oxadiargyl and oxadiazon;
N-phenyltriazolinone compounds such as azafenidine, carfentrazone-ethyl, sulfentrazone;
Phenylpyrazoles such as pyraflufen-ethyl;
Azolylcarboxamide compounds such as cafenstrole, fentrazamide, ipfencarbazone;
Benzofuran compounds such as benfuresate and etofumesate;
Isoxazoline compounds such as fenoxasulfone and pyroxasulfone;
Oxirane compounds such as indanofan and tridiphane;
butylate, cycloate, dimepiperate, EPTC, esprocarb, molinate, orbencarb, pebulate, prosulfocarb, benthiocarb, thiocarbasil Thiocarbamate compounds such as (tiocarbazil), tri-allate, and vernolate;
acetochlor, alachlor, allidochlor, butachlor, butenachlor, delachlor, diethatyl-ethyl, dimethachlor, dimethenamid, metaza α-chloros such as metazachlor, metolachlor, petoxamide, pretilachlor, propachlor, propisochlor, prynachlor, thenylchlor Acetamide compounds;
α-oxyacetamide compounds such as flufenacet and mefenacet;
α-thioacetamide compounds such as anilofos and piperophos;
Carbamate compounds such as asulam, barban, carbetamide, chlorbufam, chlorpropham, propham, swep;
Aryl carboxylate compounds such as diflufenzopyr-sodium and naptalam;
Pyridinium compounds such as cyperquat, diquat, morphamquat, paraquat;
Dinitrophenol compounds such as dinosam, dinoseb, dinoterb, DNOC, etinofen, medinoterb;
Isoxazole compounds such as isoxaflutole;
Pyrazole compounds such as benzofenap, pyrasulfotole, pyrazolynate, pyrazoxyfen, tolpyralate, topramezone;
Such as bicyclopyrone, fenquinotrione, mesotrione, sulcotrione, tefuryltrione, tembotrione, benzobicyclon, lancotrione Triketone compounds;
Alkylazine compounds such as indaziflam and triaziflam;
triazolocarboxamides such as flupoxam;
Benzyl ether compounds such as cinmethylin and methiozolin;
Diphenyl ether compounds such as aclonifen;
Pyridazinedione compounds such as cyclopyrimorate;
Triazole compounds such as amitrole;
Acetamide compounds such as diphenamide, naproanilide, and napropamide;
Arylaminopropionic acid compounds such as flamprop-m;
Phosphorodithioate compounds such as bensulide;
Chlorocarbonates such as dalapon, flupropanate, and TCA;
Trifluoromethanesulfonanilide compounds such as mefluidide and perfluidone;
Other compounds include benazolin-ethyl, pyraclonil, endothal, bromobutide, cumyluron, difenzoquat, DSMA, dymron, etobenzanide, fosamine, methyldymron, monalide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tetoflupylori tetflupyrolimet, dimesulfazet, epirifenacil, tripyrasulfone, rimisoxafen, fenpyrazone, dioxopyritrione, cypyrafluone, bipyrazone ( bipyrazone), benquitrione, fluchloraminopyr, pyriflubenzoxim, flufenoximacil, iptriazopyrid, flusulfinam, broclozone (broclozone), indolauxipyr, pyraquinate, icafolin, etc.; antiviral agents such as chloroinconazide, seboctylamine;
(Z)-11-hexadecenal, (Z)-11-hexadecenal, (Z)-11-hexadecenyl acetate, (Z)-11-tetrade Cenyl acetate ((Z)-11-tetradecenyl acetate), (Z)-9-tetradecenyl acetate ((Z)-9-tetradecenyl acetate), 10-methyl-dodecyl acetate (10-methyl- dodecyl acetate), (Z)-9-dodecenyl acetate, (Z)-9-dodecenyl acetate, 11-dodecenyl acetate, (Z)-11-tetradecen- 1-ol ((Z)-11-tetradecen-1-ol), litlure, (Z,E)-9,11-tetradecadienyl acetate ((Z,E)-9,11-tetradecadienyl acetate), (Z)-9,12-tetradecadienyl acetate, (Z)-9-tetradecen-1-ol ((Z)-9-tetradecen- Attractants such as 1-ol);
antibiotics such as bialaphos;
Indol-3-acetic acid, gibberellin, zeatin, kinetin, abscisic acid, ethylene, brassinosteroid, jasmonic acids phytohormones such as (jasmonate), strigolactone;
4-chlorophenoxyacetic acid, 1-naphthylacetamide, prohydrojasmon, aviglycine, 1-methylcyclopropene, ethephon. such as plant growth regulators.
クロジナホッププロパルギル(clodinafop-propargyl)、クロホップ(clofop)、シハロホップブチル(cyhalofop-butyl)、ジクロホップメチル(diclofop-methyl)、フェノキサプロップエチル(fenoxaprop-ethyl)、フェンチアプロップ(fenthiaprop)、フルアジホップブチル(fluazifop-butyl)、ハロキシホップメチル(haloxyfop-methyl)、イソキサピリホップ(isoxapyrifop)、メタミホップ(metamifop)、キザロホップエチル(quizalofop-ethyl)のようなアリールオキシプロピオン酸エステル系化合物;
アロキシジム(alloxydim)、ブトロキシジム(butroxydim)、クレトジム(clethodim)、クロプロキシジム(cloproxydim)、シクロキシジム(cycloxydim)、プロホキシジム(profoxydim)、セトキシジム(sethoxydim)、テプラロキシジム(tepraloxydim)、トラルコキシジム(tralkoxydim)のようなシクロヘキサンジオン系化合物;
ピノキサデン(pinoxaden)のようなフェニルピラゾリン系化合物;
イマザメタベンズメチル(imazamethabenz-methyl)、イマザモックス(imazamox)、イマザピック(imazapic)、イマザピル(imazapyr)、イマザキン(imazaquin)、イマゼタピル(imazethapyr)のようなイミダゾリノン系化合物;
ビスピリバックナトリウム塩(bispyribac-sodium)、ピリベンゾキシム(pyribenzoxim)、ピリフタリド(pyriftalid)、ピリミノバックメチル(pyriminobac-methyl)、ピリチオバックナトリウム塩(pyrithiobac-sodium)のようなピリミジニルベンゾエート系化合物;
ピリミスルファン(pyrimisulfan)、トリアファモン(triafamone)のようなスルホンアニリド系化合物;
アミドスルフロン(amidosulfuron)、アジムスルフロン(azimsulfuron)、ベンスルフロンメチル(bensulfuron-methyl)、クロリムロンエチル(chlorimuron-ethyl)、クロルスルフロン(chlorsulfuron)、シノスルフロン(cinosulfuron)、シクロスルファムロン(cyclosulfamuron)、エタメトスルフロンメチル(ethametsulfuron-methyl)、エトキシスルフロン(ethoxysulfuron)、フラザスルフロン(flazasulfuron)、フルセトスルフロン(flucetosulfuron)、フルピルスルフロンメチルナトリウム塩(flupyrsulfuron-methyl-Na)、ホラムスルフロン(foramsulfuron)、ハロスルフロンメチル(halosulfuron-methyl)、イマゾスルフロン(imazosulfuron)、ヨードスルフロンメチルナトリウム塩(iodosulfuron-methyl-Na)、メソスルフロンメチル(mesosulfuron-methyl)、メタゾスルフロン(metazosulfuron)、メトスルフロンメチル(metsulfuron-methyl)、ニコスルフロン(nicosulfuron)、オルトスルファムロン(orthosulfamuron)、オキサスルフロン(oxasulfuron)、プリミスルフロンメチル(primisulfuron-methyl)、プロピリスルフロン(propyrisulfuron)、プロスルフロン(prosulfuron)、ピラゾスルフロンエチル(pyrazosulfuron-ethyl)、リムスルフロン(rimsulfuron)、スルホメツロンメチル(sulfometuron-methyl)、スルホスルフロン(sulfosulfuron)、チフェンスルフロンメチル(thifensulfuron-methyl)、トリアスルフロン(triasulfuron)、トリベニュロンメチル(tribenuron-methyl)、トリフロキシスルフロンナトリウム塩(trifloxysulfuron-Na)、トリフルスルフロンメチル(triflusulfuron-methyl)、トリトスルフロン(tritosulfuron)のようなスルホニルウレア系化合物;
フルカルバゾンナトリウム塩(flucarbazone-Na)、プロポキシカルバゾンナトリウム塩(propoxycarbazone-Na)、チエンカルバゾンメチル(thiencarbazone-methyl)のようなトリアゾリノン系化合物;
クロランスラムメチル(cloransulam-methyl)、ジクロスラム(diclosulam)、フロラスラム(florasulam)、フルメツラム(flumetsulam)、メトスラム(metosulam)、ペノキススラム(penoxsulam)、ピロクススラム(pyroxsulam)のようなトリアゾロピリミジン系化合物;
プロピザミド(propyzamide)、テブタム(tebutam)、イソキサベン(isoxaben)のようなベンズアミド系化合物;
クロルタールジメチル(chlorthal-dimethyl)、クロランベン(chloramben)、ジカンバ(dicamba)、TCBAのような安息香酸系化合物;
ベンフルラリン(benfluralin)、ブトルアリン(butralin)、ジニトラミン(dinitramine)、エタルフルラリン(ethalfluralin)、フルクロラリン(fluchloralin)、イソプロパリン(isopropalin)、ニトラリン(nitralin)、オリザリン(oryzalin)、ペンディメタリン(pendimethalin)、プロジアミン(prodiamine)、プロフルラリン(profluralin)、トリフルラリン(trifluralin)のようなジニトロアニリン系化合物;
ブタミホス(butamifos)、DMPAのようなホスホロアミデート系化合物;
ジチオピル(dithiopyr)、チアゾピル(thiazopyr)のようなピリジン系化合物;
2,4,5-T、2,4-D、2,4-DB、クロメプロップ(clomeprop)、ジクロルプロップ(dichlorprop)、フェノプロップ(fenoprop)、MCPA、MCPB、MCPPのようなフェノキシカルボン酸系化合物;
クロルフェナック(chlorfenac)、クロルフェンプロップ(chlorfenprop)のようなフェニルカルボン酸系化合物;
アミノピラリド(aminopyralid)、クロピラリド(clopyralid)、フロルピラウキシフェン(florpyrauxifen)、ハラウキシフェン(halauxifen)、ピクロラム(picloram)のようなピリジンカルボン酸系化合物;
フルロキシピル(fluroxypyr)、トリクロピル(triclopyr)のようなピリジルオキシカルボン酸系化合物;
アミノシクロピラクロル(aminocyclopyrachlor)のようなピリミジンカルボン酸系化合物;
キンクロラック(quinclorac)、キンメラック(quinmerac)のようなキノリンカルボン酸系化合物;
クロラノクリル(chloranocryl)、CMMP、DCPAのようなアミド系化合物;
クロルプロカルブ(chlorprocarb)、デスメディファム(desmedipham)、フェニソファム(phenisopham)、フェンメディファム(phenmedipham)のようなフェニルカーバメート系化合物;
ブロムピラゾン(brompyrazon)、クロリダゾン(chloridazon)のようなピリダジノン系化合物;
アメトリン(ametryne)、アトラトン(atraton)、アトラジン(atrazine)、アジプロトリン(aziprotryne)、クロラジン(chlorazine)、シアナジン(cyanazine)、シプラジン(cyprazine)、デスメトリン(desmetryne)、ジメタメトリン(dimethametryn)、ジプロペトリン(dipropetryn)、エグリナジンエチル(eglinazine-ethyl)、イパジン(ipazine)、メトプロトリン(methoprotryne)、プロシアジン(procyazine)、プログリナジン(proglinazine-ethyl)、プロメトン(prometon)、プロメトリン(prometryne)、プロパジン(propazine)、セブチラジン(sebuthylazine)、セクブメトン(secbumeton)、シマジン(simazine)、シメトリン(simetryne)、テルブメトン(terbumeton)、テルブチラジン(terbuthylazine)、テルブトリン(terbutryne)、トリエタジン(trietazine)のようなトリアジン系化合物;
エチオジン(ethiozin)、ヘキサジノン(hexazinone)、イソメチオジン(isomethiozin)、メタミトロン(metamitron)、メトリブジン(metribuzin)のようなトリアジノン系化合物;
アミカルバゾン(amicarbazone)のようなトリアゾリノン系化合物;
ブロマシル(bromacil)、イソシル(isocil)、レナシル(lenacil)、ターバシル(terbacil)のようなウラシル系化合物;
ベンズチアズロン(benzthiazuron)、ブロムロン(bromuron)、ブツロン(buturon)、クロルブロムロン(chlorbromuron)、クロロトルロン(chlorotoluron)、クロロクスロン(chloroxuron)、ジフェノキスロン(difenoxuron)、ジメフロン(dimefuron)、ジウロン(diuron)、エチジムロン(ethidimuron)、フェニュロン(fenuron)、フルオメツロン(fluometuron)、フルオチウロン(fluothiuron)、イソプロツロン(isoproturon)、イソウロン(isouron)、リニュロン(linuron)、メタベンズチアズロン(methabenzthiazuron)、メトベンズロン(metobenzuron)、メトブロムロン(metobromuron)、メトキスロン(metoxuron)、モノリニュロン(monolinuron)、モニュロン(monuron)、ネブロン(neburon)、パラフルロン(parafluron)、シデュロン(siduron)、テブチウロン(tebuthiuron)、チアザフルロン(thiazafluron)のようなウレア系化合物;
ベンタゾン(bentazon)のようなベンゾチアジアジノン系化合物;
ブロモフェノキシム(bromofenoxim)、ブロモキシニル(bromoxynil)、アイオキシニル(ioxynil)、クロルチアミド(chlorthiamid)、ジクロベニル(dichlobenil)のようなニトリル系化合物;
ピリデート(pyridate)のようなフェニルピリダジン系化合物;
グリホサート(glyphosate)のようなグリシン系化合物;
グルホシネートアンモニウム塩(glufosinate-ammonium)のようなホスフィン酸系化合物;
フルリドン(fluridone)、フルルタモン(flurtamone)のようなジフェニルヘテロ環系化合物;
フルロクロリドン(flurochloridone)、ノルフルラゾン(norflurazon)のようなN-フェニルヘテロ環系化合物;
ベフルブタミド(beflubutamid)、ベフルブタミド-M(beflubutamid-M)、ジフルフェニカン(diflufenican)、ピコリナフェン(picolinafen)のようなフェニルエーテル系化合物;
ビキスロゾン(bixlozone)、クロマゾン(clomazone)のようなイソオキサゾリジノン系化合物;
アシフルオルフェン(acifluorfen)、ビフェノックス(bifenox)、クロメトキシフェン(chlomethoxyfen)、クロルニトロフェン(chlornitrofen)、フルロジフェン(fluorodifen)、フルオログリコフェンエチル(fluoroglycofen-ethyl)、フルオロニトロフェン(fluoronitrofen)、ホメサフェン(fomesafen)、ラクトフェン(lactofen)、ニトロフェン(nitrofen)、オキシフローフェン(oxyfluorfen)のようなジフェニルエーテル系化合物;
ブタフェナシル(butafenacil)、クロルフタリム(chlorphthalim)、シニドンエチル(cinidon-ethyl)、フルミクロラックペンチル(flumiclorac-pentyl)、フルミオキサジン(flumioxazin)、フルミプロピン(flumipropyn)、フルチアセットメチル(fluthiacet-methyl)、ペントキサゾン(pentoxazone)、サフルフェナシル(saflufenacil)、チアフェナシル(tiafenacil)、トリフルジモキサジン(trifludimoxazin)のようなN-フェニルイミド系化合物;
オキサジアルギル(oxadiargyl)、オキサジアゾン(oxadiazon)のようなN-フェニルオキサジアゾロン系化合物;
アザフェニジン(azafenidin)、カルフェントラゾンエチル(carfentrazone-ethyl)、スルフェントラゾン(sulfentrazone)のようなN-フェニルトリアゾリノン系化合物;
ピラフルフェンエチル(pyraflufen-ethyl)のようなフェニルピラゾール系化合物;
カフェンストロール(cafenstrole)、フェントラザミド(fentrazamide)、イプフェンカルバゾン(ipfencarbazone)のようなアゾリルカルボキシアミド系化合物;
ベンフレセート(benfuresate)、エトフメセート(ethofumesate)のようなベンゾフラン系化合物;
フェノキサスルホン(fenoxasulfone)、ピロキサスルホン(pyroxasulfone)のようなイソキサゾリン系化合物;
インダノファン(indanofan)、トリジファン(tridiphane)のようなオキシラン系化合物;
ブチレート(butylate)、シクロエート(cycloate)、ジメピペレート(dimepiperate)、EPTC、エスプロカルブ(esprocarb)、モリネート(molinate)、オルベンカルブ(orbencarb)、ペブレート(pebulate)、プロスルホカルブ(prosulfocarb)、ベンチオカーブ(benthiocarb)、チオカルバジル(tiocarbazil)、トリアレート(tri-allate)、バーナレート(vernolate)のようなチオカーバメート系化合物;
アセトクロール(acetochlor)、アラクロール(alachlor)、アリドクロル(allidochlor)、ブタクロール(butachlor)、ブテナクロール(butenachlor)、デラクロール(delachlor)、ジエタチルエチル(diethatyl-ethyl)、ジメタクロール(dimethachlor)、ジメテナミド(dimethenamid)、メタザクロール(metazachlor)、メトラクロール(metolachlor)、ペトキサミド(pethoxamid)、プレチラクロール(pretilachlor)、プロパクロール(propachlor)、プロピソクロール(propisochlor)、プリナクロール(prynachlor)、テニルクロール(thenylchlor)のようなα-クロロアセトアミド系化合物;
フルフェナセット(flufenacet)、メフェナセット(mefenacet)のようなα-オキシアセトアミド系化合物;
アニロホス(anilofos)、ピペロホス(piperophos)のようなα-チオアセトアミド系化合物;
アシュラム(asulam)、バルバン(barban)、カルベタミド(carbetamide)、クロルブファム(chlorbufam)、クロルプロファム(chlorpropham)、プロファム(propham)、スエップ(swep)のようなカーバメート系化合物;
ジフルフェンゾピルナトリウム塩(diflufenzopyr-sodium)、ナプタラム(naptalam)のようなアリールカルボキシレート系化合物;
シペルコート(cyperquat)、ジクワット(diquat)、モルファムコート(morfamquat)、パラコート(paraquat)のようなピリジニウム系化合物;
ジノサム(dinosam)、ジノセブ(dinoseb)、ジノテルブ(dinoterb)、DNOC、エチノフェン(etinofen)、メジノテルブ(medinoterb)のようなジニトロフェノール系化合物;
イソキサフルトール(isoxaflutole)のようなイソオキサゾール系化合物;
ベンゾフェナップ(benzofenap)、ピラスルホトール(pyrasulfotole)、ピラゾリネート(pyrazolynate)、ピラゾキシフェン(pyrazoxyfen)、トルピラレート(tolpyralate)、トプラメゾン(topramezone)のようなピラゾール系化合物;
ビシクロピロン(bicyclopyrone)、フェンキノトリオン(fenquinotrione)、メソトリオン(mesotrione)、スルコトリオン(sulcotrione)、テフリルトリオン(tefuryltrione)、テンボトリオン(tembotrione)、ベンゾビシクロン(benzobicyclon)、ランコトリオン(lancotrione)のようなトリケトン系化合物;
インダジフラム(indaziflam)、トリアジフラム(triaziflam)のようなアルキルアジン系化合物;
フルポキサム(flupoxam)のようなトリアゾロカルボキサミド系化合物;
シンメチリン(cinmethylin)、メチオゾリン(methiozolin)のようなベンジルエーテル系化合物;
アクロニフェン(aclonifen)のようなジフェニルエーテル系化合物;
シクロピリモレート(cyclopyrimorate)のようなピリダジンジオン系化合物;
アミトロール(amitrole)のようなトリアゾール系化合物;
ジフェナミド(diphenamid)、ナプロアニリド(naproanilide)、ナプロパミド(napropamide)のようなアセトアミド系化合物;
フランプロップM(flamprop-m)のようなアリールアミノプロピオン酸系化合物;
ベンスリド(bensulide)のようなホスホロジチオエート系化合物;
ダラポン(dalapon)、フルプロパネート(flupropanate)、TCAのようなクロロ炭酸系化合物;
メフルイジド(mefluidide)、ペルフルイドン(perfluidone)のようなトリフルオロメタンスルホンアニリド系化合物;
その他の化合物として、ベナゾリンエチル(benazolin-ethyl)、ピラクロニル(pyraclonil)、エンドタール(endothal)、ブロモブチド(bromobutide)、クミルロン(cumyluron)、ジフェンゾコート(difenzoquat)、DSMA、ダイムロン(dymron)、エトベンザニド(etobenzanid)、ホサミン(fosamine)、メチルダイムロン(methyldymron)、モナリッド(monalide)、MSMA、オレイン酸(oleic acid)、オキサジクロメホン(oxaziclomefone)、ペラルゴン酸(pelargonic acid)、ピリブチカルブ(pyributicarb)、キノクラミン(quinoclamine)、テトフルピロリメト(tetflupyrolimet)、ジメスルファゼット(dimesulfazet)、エピリフェナシル(epyrifenacil)、トリピラスルホン(tripyrasulfone)、リミソキサフェン(rimisoxafen)、フェンピラゾン(fenpyrazone)、ジオキソピリトリオン(dioxopyritrione)、シピラフルオン(cypyrafluone)、ビピラゾン(bipyrazone)、ベンキトリオン(benquitrione)、フルクロラミノピル(fluchloraminopyr)、ピリフルベンゾキシム(pyriflubenzoxim)、フルフェノキシマシル(flufenoximacil)、イプトリアゾピリド(iptriazopyrid)、フルスルフィナム(flusulfinam)、ブロクロゾン(broclozone)、インドルオーキシピル(indolauxipyr)、ピラキネート(pyraquinate)、イカフォリン(icafolin)など; クロロインコナジド(chloroinconazide)、セボクチラミン(seboctylamine)のような抗ウイルス剤;
(Z)-11-ヘキサデセナール、((Z)-11-hexadecenal)、(Z)-11-ヘキサデセニルアセタート、((Z)-11-hexadecenyl acetate)、(Z)-11-テトラデセニルアセタート((Z)-11-tetradecenyl acetate)、(Z)-9-テトラデセニルアセタート((Z)-9-tetradecenyl acetate)、10-メチル-ドデシルアセタート(10-methyl-dodecyl acetate)、(Z)-9-ドデセニルアセタート((Z)-9-dodecenyl acetate)、11-ドデセニルアセタート(11-dodecenyl acetate)、(Z)-11-テトラデセン-1-オール((Z)-11-tetradecen-1-ol)、リトルア(litlure)、(Z,E)-9,11-テトラデカジエニルアセタート((Z,E)-9,11-tetradecadienyl acetate)、(Z)-9,12-テトラデカジエニルアセタート((Z)-9,12-tetradecadienyl acetate)、(Z)-9-テトラデセン-1-オール((Z)-9-tetradecen-1-ol)のような誘引剤;
ビアラホス(bialaphos)のような抗生物質;
インドール-3-酢酸(indol-3-acetic acid)、ジベレリン(gibberellin)、ゼアチン(zeatin)、カイネチン(kinetin)、アブシジン酸(abscisic acid)、エチレン(ethylene)、ブラシノステロイド(brassinosteroid)、ジャスモン酸類(jasmonate)、ストリゴラクトン(strigolactone)のような植物ホルモン;
4-クロロフェノキシ酢酸(4-chlorophenoxyacetic acid)、1-ナフチルアセトアミド(1-naphthylacetamide)、プロヒドロジャスモン(prohydrojasmon)、アビグリシン(aviglycine)、1-メチルシクロプロペン(1-methylcyclopropene)、エテホン(ethephon)のような植物成長調整剤。 The active ingredient compounds (common names) of herbicides, antiviral agents, attractants, antibiotics, plant hormones, and plant growth regulators among the other agricultural and horticultural chemicals mentioned above are, for example, appropriately selected from the following compound groups. can do. Even if there is no particular description, if salts, alkyl esters, various structural isomers such as optical isomers, etc. exist in these compounds, they are naturally included.
clodinafop-propargyl, clofop, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenthiaprop , aryloxypropionic acids such as fluazifop-butyl, haloxyfop-methyl, isoxapyrifop, metamifop, quizalofop-ethyl Ester compounds;
Like alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim cyclohexanedione-based compounds;
Phenylpyrazoline compounds such as pinoxaden;
imidazolinone compounds such as imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
Pyrimidinyl benzoate compounds such as bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium;
Sulfonanilide compounds such as pyrimisulfan and triafamone;
amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron ), ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron-methyl-Na, foramsulfuron (foramsulfuron), halosulfuron-methyl, imazosulfuron (imazosulfuron), iodosulfuron-methyl-Na, mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl ( metsulfuron-methyl), nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyra pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribe Sulfonylurea compounds such as tribenuron-methyl, trifloxysulfuron-Na, triflusulfuron-methyl, tritosulfuron;
Triazolinones such as flucarbazone-Na, propoxycarbazone-Na, and thiencarbazone-methyl;
triazolopyrimidine compounds such as chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, pyroxsulam;
Benzamide compounds such as propyzamide, tebutam, isoxaben;
Benzoic acid compounds such as chlorthal-dimethyl, chloramben, dicamba, TCBA;
benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, nitralin, oryzalin, pendimethalin, Dinitroaniline compounds such as prodiamine, profluralin, trifluralin;
Phosphoramidate compounds such as butamifos, DMPA;
Pyridine compounds such as dithiopyr and thiazopyr;
Phenoxycarboxylic acids such as 2,4,5-T, 2,4-D, 2,4-DB, clomeprop, dichlorprop, fenoprop, MCPA, MCPB, MCPP Compound;
Phenylcarboxylic acid compounds such as chlorfenac and chlorfenprop;
Pyridine carboxylic acid compounds such as aminopyralid, clopyralid, florpyrauxifen, halauxifen, picloram;
Pyridyloxycarboxylic acid compounds such as fluroxypyr and triclopyr;
Pyrimidine carboxylic acid compounds such as aminocyclopyrachlor;
quinoline carboxylic acid compounds such as quinclorac and quinmerac;
Amide compounds such as chloranocryl, CMMP, DCPA;
Phenyl carbamate compounds such as chlorprocarb, desmedipham, phenisopham, phenmedipham;
Pyridazinone compounds such as brompyrazon and chloridazon;
ametrine, atraton, atrazine, aziprotryne, chlorazine, cyanazine, cyprazine, desmetrine, dimethametryn, dipropetryn , eglinazine-ethyl, ipazine, methoprotryne, procyazine, proglinazine-ethyl, prometon, prometryne, propazine, sebutylazine ( triazine compounds such as sebuthylazine, secbumeton, simazine, simetryne, terbumeton, terbuthylazine, terbutryne, trietazine;
triazinones such as ethiozin, hexazinone, isomethiozin, metamitron, metribuzin;
Triazolinone compounds such as amicarbazone;
Uracil compounds such as bromacil, isocil, lenacil, terbacil;
benzthiazuron, bromuron, buturon, chlorbromuron, chlorotoluron, chloroxuron, difenoxuron, dimefuron, diuron, ethidimuron (ethidimuron), fenuron, fluometuron, fluothiuron, isoproturon, isouron, linuron, methabenzthiazuron, metobenzuron, methobromuron ( urea compounds such as metobromuron, metoxuron, monolinuron, monuron, neburon, parafluron, siduron, tebuthiuron, thiazafluron;
Benzothiadiazinone compounds such as bentazon;
Nitriles such as bromofenoxim, bromoxynil, ioxynil, chlorthiamide, dichlobenil;
Phenylpyridazine compounds such as pyridate;
Glycine-based compounds such as glyphosate;
Phosphinic acid compounds such as glufosinate-ammonium;
Diphenyl heterocyclic compounds such as fluridone, flurtamone;
N-phenyl heterocyclic compounds such as flurochloridone, norflurazon;
Phenyl ether compounds such as beflubutamide, beflubutamid-M, diflufenican, picolinafen;
Isoxazolidinone compounds such as bixlozone and clomazone;
acifluorfen, bifenox, chlomethoxyfen, chlornitrofen, fluorodifen, fluoroglycofen-ethyl, fluoronitrofen, fomesafen, Diphenyl ether compounds such as lactofen, nitrofen, oxyfluorfen;
butafenacil, chlorphthalim, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, fluthiacet-methyl, pentoxazone ), N-phenylimide compounds such as saflufenacil, tiafenacil, trifludimoxazine;
N-phenyloxadiazolone compounds such as oxadiargyl and oxadiazon;
N-phenyltriazolinone compounds such as azafenidine, carfentrazone-ethyl, sulfentrazone;
Phenylpyrazoles such as pyraflufen-ethyl;
Azolylcarboxamide compounds such as cafenstrole, fentrazamide, ipfencarbazone;
Benzofuran compounds such as benfuresate and etofumesate;
Isoxazoline compounds such as fenoxasulfone and pyroxasulfone;
Oxirane compounds such as indanofan and tridiphane;
butylate, cycloate, dimepiperate, EPTC, esprocarb, molinate, orbencarb, pebulate, prosulfocarb, benthiocarb, thiocarbasil Thiocarbamate compounds such as (tiocarbazil), tri-allate, and vernolate;
acetochlor, alachlor, allidochlor, butachlor, butenachlor, delachlor, diethatyl-ethyl, dimethachlor, dimethenamid, metaza α-chloros such as metazachlor, metolachlor, petoxamide, pretilachlor, propachlor, propisochlor, prynachlor, thenylchlor Acetamide compounds;
α-oxyacetamide compounds such as flufenacet and mefenacet;
α-thioacetamide compounds such as anilofos and piperophos;
Carbamate compounds such as asulam, barban, carbetamide, chlorbufam, chlorpropham, propham, swep;
Aryl carboxylate compounds such as diflufenzopyr-sodium and naptalam;
Pyridinium compounds such as cyperquat, diquat, morphamquat, paraquat;
Dinitrophenol compounds such as dinosam, dinoseb, dinoterb, DNOC, etinofen, medinoterb;
Isoxazole compounds such as isoxaflutole;
Pyrazole compounds such as benzofenap, pyrasulfotole, pyrazolynate, pyrazoxyfen, tolpyralate, topramezone;
Such as bicyclopyrone, fenquinotrione, mesotrione, sulcotrione, tefuryltrione, tembotrione, benzobicyclon, lancotrione Triketone compounds;
Alkylazine compounds such as indaziflam and triaziflam;
triazolocarboxamides such as flupoxam;
Benzyl ether compounds such as cinmethylin and methiozolin;
Diphenyl ether compounds such as aclonifen;
Pyridazinedione compounds such as cyclopyrimorate;
Triazole compounds such as amitrole;
Acetamide compounds such as diphenamide, naproanilide, and napropamide;
Arylaminopropionic acid compounds such as flamprop-m;
Phosphorodithioate compounds such as bensulide;
Chlorocarbonates such as dalapon, flupropanate, and TCA;
Trifluoromethanesulfonanilide compounds such as mefluidide and perfluidone;
Other compounds include benazolin-ethyl, pyraclonil, endothal, bromobutide, cumyluron, difenzoquat, DSMA, dymron, etobenzanide, fosamine, methyldymron, monalide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tetoflupylori tetflupyrolimet, dimesulfazet, epirifenacil, tripyrasulfone, rimisoxafen, fenpyrazone, dioxopyritrione, cypyrafluone, bipyrazone ( bipyrazone), benquitrione, fluchloraminopyr, pyriflubenzoxim, flufenoximacil, iptriazopyrid, flusulfinam, broclozone (broclozone), indolauxipyr, pyraquinate, icafolin, etc.; antiviral agents such as chloroinconazide, seboctylamine;
(Z)-11-hexadecenal, (Z)-11-hexadecenal, (Z)-11-hexadecenyl acetate, (Z)-11-tetrade Cenyl acetate ((Z)-11-tetradecenyl acetate), (Z)-9-tetradecenyl acetate ((Z)-9-tetradecenyl acetate), 10-methyl-dodecyl acetate (10-methyl- dodecyl acetate), (Z)-9-dodecenyl acetate, (Z)-9-dodecenyl acetate, 11-dodecenyl acetate, (Z)-11-tetradecen- 1-ol ((Z)-11-tetradecen-1-ol), litlure, (Z,E)-9,11-tetradecadienyl acetate ((Z,E)-9,11-tetradecadienyl acetate), (Z)-9,12-tetradecadienyl acetate, (Z)-9-tetradecen-1-ol ((Z)-9-tetradecen- Attractants such as 1-ol);
antibiotics such as bialaphos;
Indol-3-acetic acid, gibberellin, zeatin, kinetin, abscisic acid, ethylene, brassinosteroid, jasmonic acids phytohormones such as (jasmonate), strigolactone;
4-chlorophenoxyacetic acid, 1-naphthylacetamide, prohydrojasmon, aviglycine, 1-methylcyclopropene, ethephon. such as plant growth regulators.
本発明の望ましい態様は以下の通りである。但し、本発明はこれらに限定されるものではない。
〔1〕式(I)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩を含む殺菌組成物。
〔2〕式(I)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩の有効量を、植物体、植物病原菌又は土壌に施用する工程を含む有害な植物病害を防除する方法。
〔3〕式(I)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔4〕R1がフッ素、塩素、又は臭素の各原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔5〕R1がフッ素、又は塩素の各原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔6〕R1がフッ素、又は臭素の各原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔7〕R1が塩素、又は臭素の各原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔8〕R1がフッ素原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔9〕R1が塩素原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔10〕R1が臭素原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔11〕R2がH、又はメチルである、前記〔3〕~〔10〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔12〕R2がHである、前記〔3〕~〔10〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔13〕R2が(C1-C3)-アルキルである、前記〔3〕~〔10〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔14〕R2がメチルである、前記〔3〕~〔10〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔15〕R3が(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、(C3-C4)-シクロアルキル、又は少なくとも1個のZで置換された(C1-C3)-アルキルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔16〕Zがシアノ、ハロゲン、(C3)-シクロアルキル、(C1-C3)-アルキルチオ、(C1-C4)-アルコキシカルボニル、又はカルボキシである、前記〔3〕~〔15〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔17〕R3が(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、(C3-C4)-シクロアルキル、又は少なくとも1個の(C1-C3)-アルキルチオで置換された(C1-C3)-アルキルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔18〕R3が(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、又は少なくとも1個の(C1-C3)-アルキルチオで置換された(C1-C3)-アルキルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔19〕R3がメチル、エチル、ノルマルプロピル、プロパルギル、アリル、シクロプロピル、又はメチルチオメチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔20〕R3がメチル、エチル、ノルマルプロピル、プロパルギル、アリル、又はシクロプロピルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔21〕R3がメチル、エチル、プロパルギル、アリル、シクロプロピル、又はメチルチオメチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔22〕R3がメチル、エチル、プロパルギル、又はアリルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔23〕R3がメチル、エチル、プロパルギル、又はメチルチオメチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔24〕R3がメチル、エチル、又はプロパルギルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔25〕R3がメチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔26〕R3がエチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔27〕R3がプロパルギルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔28〕R3がアリルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔29〕R3がシクロプロピルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔30〕R3がメチルチオメチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔31〕R4がハロゲン、(C1-C3)-アルキル、(C1-C3)-ハロアルキル、ニトロ、又はシアノである、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔32〕R4が塩素原子、フッ素原子、臭素原子、メチル、トリフルオロメチル、ニトロ、又はシアノである、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔33〕R4がメチル、塩素原子、フッ素原子、又は臭素原子である、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔34〕R4がトリフルオロメチル、塩素原子、フッ素原子、又は臭素原子である、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔35〕R4がニトロ、塩素原子、フッ素原子、又は臭素原子である、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔36〕R4がシアノ、塩素原子、フッ素原子、又は臭素原子である、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔37〕R4が塩素、フッ素、又は臭素の各原子である、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔38〕nが1から4の整数である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔39〕nが1から3の整数である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔40〕nが1から2の整数である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔41〕nが1である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔42〕nが2である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔43〕nが3である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔44〕少なくとも1個のR4がフェニル基の2位で置換する、前記〔3〕~〔43〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔45〕少なくとも1個のR4がフェニル基の3位で置換する、前記〔3〕~〔43〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔46〕少なくとも1個のR4がフェニル基の4位で置換する、前記〔3〕~〔43〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔47〕nが2であり、2個のR4がフェニル基の2位及び3位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔48〕nが2であり、2個のR4がフェニル基の2位及び4位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔49〕nが2であり、2個のR4がフェニル基の2位及び5位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔50〕nが3であり、3個のR4がフェニル基の2位、4位及び5位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔51〕nが3であり、3個のR4がフェニル基の2位、3位及び4位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔52〕nが3であり、3個のR4がフェニル基の2位、4位及び5位で置換する、又は3個のR4がフェニル基の2位、3位及び4位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔53〕式(IA)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔54〕式(IB)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔55〕式(IA)又は式(IB)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔56〕R3Aがメチル、エチル、プロパルギル、アリル又はシクロプロピルである、前記〔53〕又は前記〔55〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔57〕R3Aがメチル、エチル、又はプロパルギルである、前記〔53〕又は前記〔55〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔58〕R4Aが塩素原子、フッ素原子、臭素原子、メチル、トリフルオロメチル、ニトロ、又はシアノである、前記〔53〕及び前記〔55〕~〔57〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔59〕nが1から4の整数である前記〔53〕及び前記〔55〕~〔58〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔60〕R3Bがメチル、エチル、又はプロパルギルである、前記〔54〕又は前記〔55〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔61〕R4Bが塩素原子、フッ素原子、臭素原子、メチル、トリフルオロメチル、ニトロ、又はシアノである、前記〔54〕、前記〔55〕又は前記〔60〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔62〕nが1から4の整数である前記〔54〕、前記〔55〕、前記〔60〕又は前記〔61〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔63〕前記〔4〕~〔62〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩を含む農園芸用殺菌剤。
〔64〕前記〔4〕~〔62〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩の有効量を、植物体、植物病原菌又は土壌に施用する工程を含む有害な植物病害を防除する方法。 Desirable embodiments of the present invention are as follows. However, the present invention is not limited to these.
[1] A sterilizing composition containing a thiazolecarboxylic acid hydrazide compound represented by formula (I) or a salt thereof.
[2] A method for controlling harmful plant diseases, which comprises applying an effective amount of a thiazolecarboxylic acid hydrazide compound represented by formula (I) or a salt thereof to plants, plant pathogens, or soil.
[3] A thiazolecarboxylic acid hydrazide compound represented by formula (I) or a salt thereof.
[4] The thiazolecarboxylic acid hydrazide compound or a salt thereof according to [3] above, wherein R 1 is a fluorine, chlorine, or bromine atom.
[5] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [3] above, wherein R 1 is a fluorine or chlorine atom.
[6] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [3] above, wherein R 1 is a fluorine or bromine atom.
[7] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [3] above, wherein R 1 is a chlorine or bromine atom.
[8] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [3] above, wherein R 1 is a fluorine atom.
[9] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [3] above, wherein R 1 is a chlorine atom.
[10] The thiazolecarboxylic acid hydrazide compound or a salt thereof according to [3] above, wherein R 1 is a bromine atom.
[11] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [10] above, wherein R 2 is H or methyl.
[12] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [10] above, wherein R 2 is H.
[13] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [10] above, wherein R 2 is (C 1 -C 3 )-alkyl.
[14] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [10] above, wherein R 2 is methyl.
[15] R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, or at least 1 The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, which is (C 1 -C 3 )-alkyl substituted with Z.
[16] The above [3] to [15] where Z is cyano, halogen, (C 3 )-cycloalkyl, (C 1 -C 3 )-alkylthio, (C 1 -C 4 )-alkoxycarbonyl, or carboxy ] or a salt thereof.
[17] R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, or at least 1 The thiazole carboxylic acid hydrazide compound according to any one of [3] to [14] above, which is (C 1 -C 3 )-alkyl substituted with (C 1 -C 3 )-alkylthio, or its salt.
[18] R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, or at least one (C 1 -C 3 )-alkylthio The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, which is (C 1 -C 3 )-alkyl substituted with .
[19] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, normal propyl, propargyl, allyl, cyclopropyl, or methylthiomethyl. .
[20] The thiazole carboxylic acid hydrazide compound or a salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl.
[21] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, propargyl, allyl, cyclopropyl, or methylthiomethyl.
[22] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, propargyl, or allyl.
[23] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, propargyl, or methylthiomethyl.
[24] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, or propargyl.
[25] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl.
[26] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is ethyl.
[27] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is propargyl.
[28] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is allyl.
[29] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is cyclopropyl.
[30] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methylthiomethyl.
[31] R 4 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, nitro, or cyano, according to any one of [3] to [30] above. A thiazole carboxylic acid hydrazide compound or a salt thereof.
[32] The thiazole carboxylic acid hydrazide compound according to any one of [3] to [30] above, wherein R 4 is a chlorine atom, a fluorine atom, a bromine atom, methyl, trifluoromethyl, nitro, or cyano; That salt.
[33] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [30] above, wherein R 4 is methyl, a chlorine atom, a fluorine atom, or a bromine atom.
[34] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [30] above, wherein R 4 is trifluoromethyl, a chlorine atom, a fluorine atom, or a bromine atom.
[35] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [30] above, wherein R 4 is nitro, chlorine atom, fluorine atom, or bromine atom.
[36] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [30] above, wherein R 4 is cyano, a chlorine atom, a fluorine atom, or a bromine atom.
[37] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [30] above, wherein R 4 is a chlorine, fluorine, or bromine atom.
[38] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is an integer from 1 to 4.
[39] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is an integer from 1 to 3.
[40] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is an integer of 1 to 2.
[41] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is 1.
[42] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is 2.
[43] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is 3.
[44] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [43] above, wherein at least one R 4 is substituted at the 2-position of the phenyl group.
[45] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [43] above, wherein at least one R 4 is substituted at the 3-position of the phenyl group.
[46] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [43] above, wherein at least one R 4 is substituted at the 4-position of the phenyl group.
[47] The thiazole carboxylic acid hydrazide compound or its compound according to any one of [3] to [37] above, wherein n is 2 and two R 4 are substituted at the 2- and 3-positions of the phenyl group. salt.
[48] The thiazole carboxylic acid hydrazide compound or its compound according to any one of [3] to [37] above, wherein n is 2 and two R 4 are substituted at the 2- and 4-positions of the phenyl group. salt.
[49] The thiazole carboxylic acid hydrazide compound or its compound according to any one of [3] to [37] above, wherein n is 2 and two R 4 are substituted at the 2- and 5-positions of the phenyl group. salt.
[50] The thiazolecarboxylic acid hydrazide according to any one of [3] to [37] above, wherein n is 3 and three R 4 are substituted at the 2-, 4-, and 5-positions of the phenyl group. Compound or its salt.
[51] The thiazolecarboxylic acid hydrazide according to any one of [3] to [37] above, wherein n is 3 and three R 4 are substituted at the 2-, 3-, and 4-positions of the phenyl group. Compound or its salt.
[52] n is 3, and three R4s are substituted at the 2nd, 4th, and 5th positions of the phenyl group, or three R4s are substituted at the 2nd, 3rd, and 4th positions of the phenyl group The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above.
[53] A thiazolecarboxylic acid hydrazide compound represented by formula (IA) or a salt thereof.
[54] A thiazolecarboxylic acid hydrazide compound represented by formula (IB) or a salt thereof.
[55] A thiazolecarboxylic acid hydrazide compound represented by formula (IA) or formula (IB) or a salt thereof.
[56] The thiazole carboxylic acid hydrazide compound or a salt thereof according to the above [53] or [55], wherein R 3A is methyl, ethyl, propargyl, allyl, or cyclopropyl.
[57] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [53] or [55] above, wherein R 3A is methyl, ethyl, or propargyl.
[58] The thiazole according to any one of [53] and [55] to [57] above, wherein R 4A is a chlorine atom, a fluorine atom, a bromine atom, methyl, trifluoromethyl, nitro, or cyano. Carboxylic acid hydrazide compound or its salt.
[59] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of the above [53] and [55] to [58], wherein n is an integer from 1 to 4.
[60] The thiazole carboxylic acid hydrazide compound or salt thereof according to [54] or [55] above, wherein R 3B is methyl, ethyl, or propargyl.
[61] The thiazole carboxylic acid hydrazide compound according to the above [54], [55] or [60], wherein R 4B is a chlorine atom, a fluorine atom, a bromine atom, methyl, trifluoromethyl, nitro, or cyano. Or its salt.
[62] The thiazole carboxylic acid hydrazide compound or a salt thereof according to the above [54], [55], [60] or [61], wherein n is an integer from 1 to 4.
[63] An agricultural and horticultural fungicide comprising the thiazolecarboxylic acid hydrazide compound or its salt according to any one of [4] to [62] above.
[64] A method for preventing harmful plant diseases comprising applying an effective amount of the thiazolecarboxylic acid hydrazide compound or its salt according to any one of [4] to [62] above to plants, plant pathogenic bacteria, or soil. How to control.
〔1〕式(I)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩を含む殺菌組成物。
〔2〕式(I)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩の有効量を、植物体、植物病原菌又は土壌に施用する工程を含む有害な植物病害を防除する方法。
〔3〕式(I)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔4〕R1がフッ素、塩素、又は臭素の各原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔5〕R1がフッ素、又は塩素の各原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔6〕R1がフッ素、又は臭素の各原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔7〕R1が塩素、又は臭素の各原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔8〕R1がフッ素原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔9〕R1が塩素原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔10〕R1が臭素原子である、前記〔3〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔11〕R2がH、又はメチルである、前記〔3〕~〔10〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔12〕R2がHである、前記〔3〕~〔10〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔13〕R2が(C1-C3)-アルキルである、前記〔3〕~〔10〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔14〕R2がメチルである、前記〔3〕~〔10〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔15〕R3が(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、(C3-C4)-シクロアルキル、又は少なくとも1個のZで置換された(C1-C3)-アルキルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔16〕Zがシアノ、ハロゲン、(C3)-シクロアルキル、(C1-C3)-アルキルチオ、(C1-C4)-アルコキシカルボニル、又はカルボキシである、前記〔3〕~〔15〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔17〕R3が(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、(C3-C4)-シクロアルキル、又は少なくとも1個の(C1-C3)-アルキルチオで置換された(C1-C3)-アルキルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔18〕R3が(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、又は少なくとも1個の(C1-C3)-アルキルチオで置換された(C1-C3)-アルキルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔19〕R3がメチル、エチル、ノルマルプロピル、プロパルギル、アリル、シクロプロピル、又はメチルチオメチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔20〕R3がメチル、エチル、ノルマルプロピル、プロパルギル、アリル、又はシクロプロピルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔21〕R3がメチル、エチル、プロパルギル、アリル、シクロプロピル、又はメチルチオメチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔22〕R3がメチル、エチル、プロパルギル、又はアリルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔23〕R3がメチル、エチル、プロパルギル、又はメチルチオメチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔24〕R3がメチル、エチル、又はプロパルギルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔25〕R3がメチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔26〕R3がエチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔27〕R3がプロパルギルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔28〕R3がアリルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔29〕R3がシクロプロピルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔30〕R3がメチルチオメチルである、前記〔3〕~〔14〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔31〕R4がハロゲン、(C1-C3)-アルキル、(C1-C3)-ハロアルキル、ニトロ、又はシアノである、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔32〕R4が塩素原子、フッ素原子、臭素原子、メチル、トリフルオロメチル、ニトロ、又はシアノである、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔33〕R4がメチル、塩素原子、フッ素原子、又は臭素原子である、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔34〕R4がトリフルオロメチル、塩素原子、フッ素原子、又は臭素原子である、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔35〕R4がニトロ、塩素原子、フッ素原子、又は臭素原子である、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔36〕R4がシアノ、塩素原子、フッ素原子、又は臭素原子である、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔37〕R4が塩素、フッ素、又は臭素の各原子である、前記〔3〕~〔30〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔38〕nが1から4の整数である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔39〕nが1から3の整数である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔40〕nが1から2の整数である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔41〕nが1である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔42〕nが2である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔43〕nが3である前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔44〕少なくとも1個のR4がフェニル基の2位で置換する、前記〔3〕~〔43〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔45〕少なくとも1個のR4がフェニル基の3位で置換する、前記〔3〕~〔43〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔46〕少なくとも1個のR4がフェニル基の4位で置換する、前記〔3〕~〔43〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔47〕nが2であり、2個のR4がフェニル基の2位及び3位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔48〕nが2であり、2個のR4がフェニル基の2位及び4位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔49〕nが2であり、2個のR4がフェニル基の2位及び5位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔50〕nが3であり、3個のR4がフェニル基の2位、4位及び5位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔51〕nが3であり、3個のR4がフェニル基の2位、3位及び4位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔52〕nが3であり、3個のR4がフェニル基の2位、4位及び5位で置換する、又は3個のR4がフェニル基の2位、3位及び4位で置換する、前記〔3〕~〔37〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔53〕式(IA)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔54〕式(IB)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔55〕式(IA)又は式(IB)で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔56〕R3Aがメチル、エチル、プロパルギル、アリル又はシクロプロピルである、前記〔53〕又は前記〔55〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔57〕R3Aがメチル、エチル、又はプロパルギルである、前記〔53〕又は前記〔55〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔58〕R4Aが塩素原子、フッ素原子、臭素原子、メチル、トリフルオロメチル、ニトロ、又はシアノである、前記〔53〕及び前記〔55〕~〔57〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔59〕nが1から4の整数である前記〔53〕及び前記〔55〕~〔58〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔60〕R3Bがメチル、エチル、又はプロパルギルである、前記〔54〕又は前記〔55〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔61〕R4Bが塩素原子、フッ素原子、臭素原子、メチル、トリフルオロメチル、ニトロ、又はシアノである、前記〔54〕、前記〔55〕又は前記〔60〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔62〕nが1から4の整数である前記〔54〕、前記〔55〕、前記〔60〕又は前記〔61〕に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。
〔63〕前記〔4〕~〔62〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩を含む農園芸用殺菌剤。
〔64〕前記〔4〕~〔62〕のいずれか1つに記載のチアゾールカルボン酸ヒドラジド化合物又はその塩の有効量を、植物体、植物病原菌又は土壌に施用する工程を含む有害な植物病害を防除する方法。 Desirable embodiments of the present invention are as follows. However, the present invention is not limited to these.
[1] A sterilizing composition containing a thiazolecarboxylic acid hydrazide compound represented by formula (I) or a salt thereof.
[2] A method for controlling harmful plant diseases, which comprises applying an effective amount of a thiazolecarboxylic acid hydrazide compound represented by formula (I) or a salt thereof to plants, plant pathogens, or soil.
[3] A thiazolecarboxylic acid hydrazide compound represented by formula (I) or a salt thereof.
[4] The thiazolecarboxylic acid hydrazide compound or a salt thereof according to [3] above, wherein R 1 is a fluorine, chlorine, or bromine atom.
[5] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [3] above, wherein R 1 is a fluorine or chlorine atom.
[6] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [3] above, wherein R 1 is a fluorine or bromine atom.
[7] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [3] above, wherein R 1 is a chlorine or bromine atom.
[8] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [3] above, wherein R 1 is a fluorine atom.
[9] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [3] above, wherein R 1 is a chlorine atom.
[10] The thiazolecarboxylic acid hydrazide compound or a salt thereof according to [3] above, wherein R 1 is a bromine atom.
[11] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [10] above, wherein R 2 is H or methyl.
[12] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [10] above, wherein R 2 is H.
[13] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [10] above, wherein R 2 is (C 1 -C 3 )-alkyl.
[14] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [10] above, wherein R 2 is methyl.
[15] R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, or at least 1 The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, which is (C 1 -C 3 )-alkyl substituted with Z.
[16] The above [3] to [15] where Z is cyano, halogen, (C 3 )-cycloalkyl, (C 1 -C 3 )-alkylthio, (C 1 -C 4 )-alkoxycarbonyl, or carboxy ] or a salt thereof.
[17] R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, or at least 1 The thiazole carboxylic acid hydrazide compound according to any one of [3] to [14] above, which is (C 1 -C 3 )-alkyl substituted with (C 1 -C 3 )-alkylthio, or its salt.
[18] R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, or at least one (C 1 -C 3 )-alkylthio The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, which is (C 1 -C 3 )-alkyl substituted with .
[19] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, normal propyl, propargyl, allyl, cyclopropyl, or methylthiomethyl. .
[20] The thiazole carboxylic acid hydrazide compound or a salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl.
[21] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, propargyl, allyl, cyclopropyl, or methylthiomethyl.
[22] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, propargyl, or allyl.
[23] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, propargyl, or methylthiomethyl.
[24] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl, ethyl, or propargyl.
[25] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methyl.
[26] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is ethyl.
[27] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is propargyl.
[28] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is allyl.
[29] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is cyclopropyl.
[30] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [14] above, wherein R 3 is methylthiomethyl.
[31] R 4 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, nitro, or cyano, according to any one of [3] to [30] above. A thiazole carboxylic acid hydrazide compound or a salt thereof.
[32] The thiazole carboxylic acid hydrazide compound according to any one of [3] to [30] above, wherein R 4 is a chlorine atom, a fluorine atom, a bromine atom, methyl, trifluoromethyl, nitro, or cyano; That salt.
[33] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [30] above, wherein R 4 is methyl, a chlorine atom, a fluorine atom, or a bromine atom.
[34] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [30] above, wherein R 4 is trifluoromethyl, a chlorine atom, a fluorine atom, or a bromine atom.
[35] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [30] above, wherein R 4 is nitro, chlorine atom, fluorine atom, or bromine atom.
[36] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [30] above, wherein R 4 is cyano, a chlorine atom, a fluorine atom, or a bromine atom.
[37] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [30] above, wherein R 4 is a chlorine, fluorine, or bromine atom.
[38] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is an integer from 1 to 4.
[39] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is an integer from 1 to 3.
[40] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is an integer of 1 to 2.
[41] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is 1.
[42] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is 2.
[43] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above, wherein n is 3.
[44] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [43] above, wherein at least one R 4 is substituted at the 2-position of the phenyl group.
[45] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [43] above, wherein at least one R 4 is substituted at the 3-position of the phenyl group.
[46] The thiazole carboxylic acid hydrazide compound or salt thereof according to any one of [3] to [43] above, wherein at least one R 4 is substituted at the 4-position of the phenyl group.
[47] The thiazole carboxylic acid hydrazide compound or its compound according to any one of [3] to [37] above, wherein n is 2 and two R 4 are substituted at the 2- and 3-positions of the phenyl group. salt.
[48] The thiazole carboxylic acid hydrazide compound or its compound according to any one of [3] to [37] above, wherein n is 2 and two R 4 are substituted at the 2- and 4-positions of the phenyl group. salt.
[49] The thiazole carboxylic acid hydrazide compound or its compound according to any one of [3] to [37] above, wherein n is 2 and two R 4 are substituted at the 2- and 5-positions of the phenyl group. salt.
[50] The thiazolecarboxylic acid hydrazide according to any one of [3] to [37] above, wherein n is 3 and three R 4 are substituted at the 2-, 4-, and 5-positions of the phenyl group. Compound or its salt.
[51] The thiazolecarboxylic acid hydrazide according to any one of [3] to [37] above, wherein n is 3 and three R 4 are substituted at the 2-, 3-, and 4-positions of the phenyl group. Compound or its salt.
[52] n is 3, and three R4s are substituted at the 2nd, 4th, and 5th positions of the phenyl group, or three R4s are substituted at the 2nd, 3rd, and 4th positions of the phenyl group The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of [3] to [37] above.
[53] A thiazolecarboxylic acid hydrazide compound represented by formula (IA) or a salt thereof.
[54] A thiazolecarboxylic acid hydrazide compound represented by formula (IB) or a salt thereof.
[55] A thiazolecarboxylic acid hydrazide compound represented by formula (IA) or formula (IB) or a salt thereof.
[56] The thiazole carboxylic acid hydrazide compound or a salt thereof according to the above [53] or [55], wherein R 3A is methyl, ethyl, propargyl, allyl, or cyclopropyl.
[57] The thiazolecarboxylic acid hydrazide compound or salt thereof according to [53] or [55] above, wherein R 3A is methyl, ethyl, or propargyl.
[58] The thiazole according to any one of [53] and [55] to [57] above, wherein R 4A is a chlorine atom, a fluorine atom, a bromine atom, methyl, trifluoromethyl, nitro, or cyano. Carboxylic acid hydrazide compound or its salt.
[59] The thiazolecarboxylic acid hydrazide compound or salt thereof according to any one of the above [53] and [55] to [58], wherein n is an integer from 1 to 4.
[60] The thiazole carboxylic acid hydrazide compound or salt thereof according to [54] or [55] above, wherein R 3B is methyl, ethyl, or propargyl.
[61] The thiazole carboxylic acid hydrazide compound according to the above [54], [55] or [60], wherein R 4B is a chlorine atom, a fluorine atom, a bromine atom, methyl, trifluoromethyl, nitro, or cyano. Or its salt.
[62] The thiazole carboxylic acid hydrazide compound or a salt thereof according to the above [54], [55], [60] or [61], wherein n is an integer from 1 to 4.
[63] An agricultural and horticultural fungicide comprising the thiazolecarboxylic acid hydrazide compound or its salt according to any one of [4] to [62] above.
[64] A method for preventing harmful plant diseases comprising applying an effective amount of the thiazolecarboxylic acid hydrazide compound or its salt according to any one of [4] to [62] above to plants, plant pathogenic bacteria, or soil. How to control.
次に本発明の実施例を記載するが、本発明はこれらに限定されるものではない。なお、本発明化合物の1H-NMRスペクトルデータは、測定溶媒中で、JEOL JNM-ECX(500MHz)又はBruker AVANCE III HD(300MHz)にて測定した(1H-核磁気共鳴分光法)。なお、測定溶媒は内部標準としてテトラメチルシラン(TMS)を含む場合もある。
また、本明細書において、室温は10~30℃程度を意味する。 Next, examples of the present invention will be described, but the present invention is not limited thereto. The 1 H-NMR spectrum data of the compound of the present invention was measured in a measurement solvent using JEOL JNM-ECX (500 MHz) or Bruker AVANCE III HD (300 MHz) (1 H-nuclear magnetic resonance spectroscopy). Note that the measurement solvent may contain tetramethylsilane (TMS) as an internal standard.
Furthermore, in this specification, room temperature means approximately 10 to 30°C.
また、本明細書において、室温は10~30℃程度を意味する。 Next, examples of the present invention will be described, but the present invention is not limited thereto. The 1 H-NMR spectrum data of the compound of the present invention was measured in a measurement solvent using JEOL JNM-ECX (500 MHz) or Bruker AVANCE III HD (300 MHz) (1 H-nuclear magnetic resonance spectroscopy). Note that the measurement solvent may contain tetramethylsilane (TMS) as an internal standard.
Furthermore, in this specification, room temperature means approximately 10 to 30°C.
[合成例]
合成例1:2-アミノ-4-クロロ-N-(2-クロロ-5-フルオロベンジル)-N’-メチルチアゾール-5-カルボヒドラジド(化合物No.33)の合成
(1)1-Boc-1-メチルヒドラジン(1.66g)、トリエチルアミン(1.58mL)のメタノール(50mL)溶液に少量のメタノールに溶かした2-クロロ-5-フルオロベンズアルデヒド(1.50g)を加え、室温にて終夜撹拌した。その後、氷冷下、2-ピコリンボラン(1.52g,85%)を加え、続いて3N塩酸水溶液(15.77mL)をゆっくり加えた後、室温にて2.5時間撹拌し反応溶液を得た。飽和炭酸水素ナトリウム水溶液を用いて前記反応溶液をクエンチした。クエンチした反応溶液を、3N水酸化ナトリウム水溶液を用いて塩基性とした後、酢酸エチルを用いて抽出した。抽出により得られた有機層を飽和炭酸水素ナトリウム水溶液で洗浄し、無水硫酸マグネシウムで乾燥、ろ過した後、減圧下濃縮した。得られた残渣をカラムクロマトグラフィー(溶離液:酢酸エチル/ヘプタン)で精製して、油状のtert-ブチル 2-(2-クロロ-5-フルオロベンジル)-1-メチルヒドラジン-1-カルボキシレート(1.28g)を得た。
1H NMR (CDCl3/300MHz):δ(ppm)= 7.32 (dd, 1H), 7.14 (dd, 1H), 6.94 (td, 1H), 4.78 (brs, 1H), 4.04 (d, 2H), 2.98 (s, 3H), 1.45 (s, 9H). [Synthesis example]
Synthesis Example 1: Synthesis of 2-amino-4-chloro-N-(2-chloro-5-fluorobenzyl)-N'-methylthiazole-5-carbohydrazide (Compound No. 33) (1) 1-Boc- To a methanol (50 mL) solution of 1-methylhydrazine (1.66 g) and triethylamine (1.58 mL) was added 2-chloro-5-fluorobenzaldehyde (1.50 g) dissolved in a small amount of methanol, and the mixture was stirred at room temperature overnight. did. Then, under ice cooling, 2-picoline borane (1.52 g, 85%) was added, followed by slow addition of 3N hydrochloric acid aqueous solution (15.77 mL), and the mixture was stirred at room temperature for 2.5 hours to obtain a reaction solution. Ta. The reaction solution was quenched using saturated aqueous sodium bicarbonate solution. The quenched reaction solution was made basic using 3N aqueous sodium hydroxide solution, and then extracted using ethyl acetate. The organic layer obtained by the extraction was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate/heptane) to obtain oily tert-butyl 2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1-carboxylate ( 1.28g) was obtained.
1 H NMR (CDCl 3 /300MHz):δ(ppm)= 7.32 (dd, 1H), 7.14 (dd, 1H), 6.94 (td, 1H), 4.78 (brs, 1H), 4.04 (d, 2H), 2.98 (s, 3H), 1.45 (s, 9H).
合成例1:2-アミノ-4-クロロ-N-(2-クロロ-5-フルオロベンジル)-N’-メチルチアゾール-5-カルボヒドラジド(化合物No.33)の合成
(1)1-Boc-1-メチルヒドラジン(1.66g)、トリエチルアミン(1.58mL)のメタノール(50mL)溶液に少量のメタノールに溶かした2-クロロ-5-フルオロベンズアルデヒド(1.50g)を加え、室温にて終夜撹拌した。その後、氷冷下、2-ピコリンボラン(1.52g,85%)を加え、続いて3N塩酸水溶液(15.77mL)をゆっくり加えた後、室温にて2.5時間撹拌し反応溶液を得た。飽和炭酸水素ナトリウム水溶液を用いて前記反応溶液をクエンチした。クエンチした反応溶液を、3N水酸化ナトリウム水溶液を用いて塩基性とした後、酢酸エチルを用いて抽出した。抽出により得られた有機層を飽和炭酸水素ナトリウム水溶液で洗浄し、無水硫酸マグネシウムで乾燥、ろ過した後、減圧下濃縮した。得られた残渣をカラムクロマトグラフィー(溶離液:酢酸エチル/ヘプタン)で精製して、油状のtert-ブチル 2-(2-クロロ-5-フルオロベンジル)-1-メチルヒドラジン-1-カルボキシレート(1.28g)を得た。
1H NMR (CDCl3/300MHz):δ(ppm)= 7.32 (dd, 1H), 7.14 (dd, 1H), 6.94 (td, 1H), 4.78 (brs, 1H), 4.04 (d, 2H), 2.98 (s, 3H), 1.45 (s, 9H). [Synthesis example]
Synthesis Example 1: Synthesis of 2-amino-4-chloro-N-(2-chloro-5-fluorobenzyl)-N'-methylthiazole-5-carbohydrazide (Compound No. 33) (1) 1-Boc- To a methanol (50 mL) solution of 1-methylhydrazine (1.66 g) and triethylamine (1.58 mL) was added 2-chloro-5-fluorobenzaldehyde (1.50 g) dissolved in a small amount of methanol, and the mixture was stirred at room temperature overnight. did. Then, under ice cooling, 2-picoline borane (1.52 g, 85%) was added, followed by slow addition of 3N hydrochloric acid aqueous solution (15.77 mL), and the mixture was stirred at room temperature for 2.5 hours to obtain a reaction solution. Ta. The reaction solution was quenched using saturated aqueous sodium bicarbonate solution. The quenched reaction solution was made basic using 3N aqueous sodium hydroxide solution, and then extracted using ethyl acetate. The organic layer obtained by the extraction was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate/heptane) to obtain oily tert-butyl 2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1-carboxylate ( 1.28g) was obtained.
1 H NMR (CDCl 3 /300MHz):δ(ppm)= 7.32 (dd, 1H), 7.14 (dd, 1H), 6.94 (td, 1H), 4.78 (brs, 1H), 4.04 (d, 2H), 2.98 (s, 3H), 1.45 (s, 9H).
(2)Bioorganic & Medicinal Chemistry、2004、12、6171-6182に基づき合成した2-[(tert-ブトキシカルボニル)アミノ]-4-クロロチアゾール-5-カルボン酸(0.30g)のテトラヒドロフラン(10mL)溶液に、氷冷下、塩化オキサリル(0.27g)、触媒量のN,N-ジメチルホルムアミドを加えて、40℃にて3時間撹拌し反応溶液を得た。放冷後、その反応溶液を減圧下濃縮し、2-[(tert-ブトキシカルボニル)アミノ]-4-クロロチアゾール-5-カルボン酸クロライドを得た。次に、tert-ブチル 2-(2-クロロ-5-フルオロベンジル)-1-メチルヒドラジン-1-カルボキシレート(0.26g)のテトラヒドロフラン(3mL)溶液に氷冷下、水素化ナトリウム(0.04g、60%)を加え、同温度で15分撹拌させ反応溶液を得た。その反応溶液に、調製したカルボン酸クロライドのテトラヒドロフラン(10mL)溶液を加え、室温にて4時間撹拌し、反応溶液を得た。反応終了後、氷冷下、前記反応溶液に飽和炭酸水素ナトリウム水溶液を加えて反応をクエンチした。クエンチした反応溶液を、3N水酸化ナトリウム水溶液を用いて、塩基性にした後、水層を酢酸エチルとヘプタンを用いて抽出した。続いて、抽出により得られた有機層を3N水酸化ナトリウム水溶液、飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥、ろ過した後、減圧下濃縮した。得られた残渣をカラムクロマトグラフィー(溶離液:酢酸エチル/ヘプタン)で精製して、ガム状のtert-ブチル 2-{2-[(tert-ブトキシカルボニル)アミノ]-4-クロロチアゾール-5-カルボニル}-2-(2-クロロ-5-フルオロベンジル)-1-メチルヒドラジン-1-カルボキシレート(0.36g)を得た。
1H NMR (CDCl3/300MHz):δ(ppm)= 8.65 (brs, 1H), 7.37-7.31 (m, 2H), 7.02-6.95 (m, 1H), 5.10 (brs, 1H), 4.78 (d, 1H), 3.00 (brs, 3H), 1.53 (s, 9H), 1.34 (brs, 9H). (2) 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid (0.30 g) synthesized based on Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182 in tetrahydrofuran (10 mL) Oxalyl chloride (0.27 g) and a catalytic amount of N,N-dimethylformamide were added to the solution under ice cooling, and the mixture was stirred at 40° C. for 3 hours to obtain a reaction solution. After cooling, the reaction solution was concentrated under reduced pressure to obtain 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid chloride. Next, a solution of tert-butyl 2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1-carboxylate (0.26 g) in tetrahydrofuran (3 mL) was added to a solution of sodium hydride (0.5 mL) under ice cooling. 04 g, 60%) was added thereto and stirred at the same temperature for 15 minutes to obtain a reaction solution. A solution of the prepared carboxylic acid chloride in tetrahydrofuran (10 mL) was added to the reaction solution, and the mixture was stirred at room temperature for 4 hours to obtain a reaction solution. After the reaction was completed, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution under ice cooling to quench the reaction. The quenched reaction solution was made basic using 3N aqueous sodium hydroxide solution, and then the aqueous layer was extracted using ethyl acetate and heptane. Subsequently, the organic layer obtained by the extraction was washed successively with a 3N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate/heptane) to give gummy tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5- Carbonyl}-2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1-carboxylate (0.36 g) was obtained.
1 H NMR (CDCl 3 /300MHz):δ(ppm)= 8.65 (brs, 1H), 7.37-7.31 (m, 2H), 7.02-6.95 (m, 1H), 5.10 (brs, 1H), 4.78 (d , 1H), 3.00 (brs, 3H), 1.53 (s, 9H), 1.34 (brs, 9H).
1H NMR (CDCl3/300MHz):δ(ppm)= 8.65 (brs, 1H), 7.37-7.31 (m, 2H), 7.02-6.95 (m, 1H), 5.10 (brs, 1H), 4.78 (d, 1H), 3.00 (brs, 3H), 1.53 (s, 9H), 1.34 (brs, 9H). (2) 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid (0.30 g) synthesized based on Bioorganic & Medicinal Chemistry, 2004, 12, 6171-6182 in tetrahydrofuran (10 mL) Oxalyl chloride (0.27 g) and a catalytic amount of N,N-dimethylformamide were added to the solution under ice cooling, and the mixture was stirred at 40° C. for 3 hours to obtain a reaction solution. After cooling, the reaction solution was concentrated under reduced pressure to obtain 2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carboxylic acid chloride. Next, a solution of tert-butyl 2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1-carboxylate (0.26 g) in tetrahydrofuran (3 mL) was added to a solution of sodium hydride (0.5 mL) under ice cooling. 04 g, 60%) was added thereto and stirred at the same temperature for 15 minutes to obtain a reaction solution. A solution of the prepared carboxylic acid chloride in tetrahydrofuran (10 mL) was added to the reaction solution, and the mixture was stirred at room temperature for 4 hours to obtain a reaction solution. After the reaction was completed, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution under ice cooling to quench the reaction. The quenched reaction solution was made basic using 3N aqueous sodium hydroxide solution, and then the aqueous layer was extracted using ethyl acetate and heptane. Subsequently, the organic layer obtained by the extraction was washed successively with a 3N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate/heptane) to give gummy tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5- Carbonyl}-2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1-carboxylate (0.36 g) was obtained.
1 H NMR (CDCl 3 /300MHz):δ(ppm)= 8.65 (brs, 1H), 7.37-7.31 (m, 2H), 7.02-6.95 (m, 1H), 5.10 (brs, 1H), 4.78 (d , 1H), 3.00 (brs, 3H), 1.53 (s, 9H), 1.34 (brs, 9H).
(3)tert-ブチル 2-{2-[(tert-ブトキシカルボニル)アミノ]-4-クロロチアゾール-5-カルボニル}-2-(2-クロロ-5-フルオロベンジル)-1-メチルヒドラジン-1-カルボキシレート(0.36g)、2,6-ジメチルピリジン(0.91mL)のジクロロメタン(2.6mL)溶液に氷冷下、トリフルオロメタンスルホン酸トリメチルシリル(1.17mL)を加えた。同温度で15分撹拌した後、室温にて一晩撹拌し反応溶液を得た。その後、氷冷下、前記反応溶液に飽和塩化アンモニウム水溶液をゆっくり加え反応をクエンチした。クエンチした反応溶液を、酢酸エチルを用いて抽出した。抽出により得られた有機層を飽和炭酸水素ナトリウム水溶液、飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥、ろ過した後、減圧下濃縮した。得られた残渣をカラムクロマトグラフィー(溶離液:エタノール/酢酸エチル/ヘプタン)で精製して、固体の目的物(0.20g)を得た。
1H NMR (acetone-d6/300MHz):δ(ppm)= 7.51-7.45 (m, 1H), 7.15-7.08 (m, 2H), 6.91 (brs, 2H), 4.93 (s, 2H), 4.80 (q, 1H), 2.64 (d, 3H). (3) tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carbonyl}-2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1 To a solution of -carboxylate (0.36 g) and 2,6-dimethylpyridine (0.91 mL) in dichloromethane (2.6 mL) was added trimethylsilyl trifluoromethanesulfonate (1.17 mL) under ice cooling. After stirring at the same temperature for 15 minutes, the mixture was stirred at room temperature overnight to obtain a reaction solution. Thereafter, a saturated aqueous ammonium chloride solution was slowly added to the reaction solution under ice cooling to quench the reaction. The quenched reaction solution was extracted using ethyl acetate. The organic layer obtained by the extraction was washed successively with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent: ethanol/ethyl acetate/heptane) to obtain the target product (0.20 g) as a solid.
1 H NMR (acetone-d 6 /300MHz):δ(ppm)= 7.51-7.45 (m, 1H), 7.15-7.08 (m, 2H), 6.91 (brs, 2H), 4.93 (s, 2H), 4.80 (q, 1H), 2.64 (d, 3H).
1H NMR (acetone-d6/300MHz):δ(ppm)= 7.51-7.45 (m, 1H), 7.15-7.08 (m, 2H), 6.91 (brs, 2H), 4.93 (s, 2H), 4.80 (q, 1H), 2.64 (d, 3H). (3) tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carbonyl}-2-(2-chloro-5-fluorobenzyl)-1-methylhydrazine-1 To a solution of -carboxylate (0.36 g) and 2,6-dimethylpyridine (0.91 mL) in dichloromethane (2.6 mL) was added trimethylsilyl trifluoromethanesulfonate (1.17 mL) under ice cooling. After stirring at the same temperature for 15 minutes, the mixture was stirred at room temperature overnight to obtain a reaction solution. Thereafter, a saturated aqueous ammonium chloride solution was slowly added to the reaction solution under ice cooling to quench the reaction. The quenched reaction solution was extracted using ethyl acetate. The organic layer obtained by the extraction was washed successively with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent: ethanol/ethyl acetate/heptane) to obtain the target product (0.20 g) as a solid.
1 H NMR (acetone-d 6 /300MHz):δ(ppm)= 7.51-7.45 (m, 1H), 7.15-7.08 (m, 2H), 6.91 (brs, 2H), 4.93 (s, 2H), 4.80 (q, 1H), 2.64 (d, 3H).
合成例2:2-アミノ-4-クロロ-N-(4-フルオロ-2-メチルベンジル)-N’-メチルチアゾール-5-カルボヒドラジド(化合物No.105)の合成
(1)4-フルオロ-2-メチルベンズアルデヒド(1.0g)と1-Boc-1-メチルヒドラジン(1.06g)のエタノール(35mL)溶液を75℃で3時間撹拌した。室温に冷却後、2-ピコリンボラン(1.82g、85%)および3N 塩酸水溶液(12mL)を加え、室温で一晩撹拌し反応混合液を得た。前記反応混合液に飽和炭酸水素ナトリウム水溶液を加え得られた反応混合物を、減圧下濃縮した。残渣に酢酸エチルを加え、水層を酢酸エチルで抽出した。抽出により得られた有機層を水、飽和食塩水で順次洗浄し、無水硫酸ナトリウムで乾燥、ろ過したあと、減圧下濃縮した。得られた残渣をカラムクロマトグラフィー(溶離液:酢酸エチル/ヘプタン)で精製して、油状のtert-ブチル 2-(4-フルオロ-2-メチルベンジル)-1-メチルヒドラジン-1-カルボキシレ-ト(1.68g)を得た。
1H NMR (CDCl3/300MHz):δ(ppm) = 7.23-7.18 (m, 1H), 6.90-6.80 (m, 2H), 4.53 (brs, 1H), 3.92 (s, 2H), 2.92 (s, 3H), 2.42 (s, 3H), 1.49 (s, 9H). Synthesis Example 2: Synthesis of 2-amino-4-chloro-N-(4-fluoro-2-methylbenzyl)-N'-methylthiazole-5-carbohydrazide (compound No. 105) (1) 4-fluoro- A solution of 2-methylbenzaldehyde (1.0 g) and 1-Boc-1-methylhydrazine (1.06 g) in ethanol (35 mL) was stirred at 75° C. for 3 hours. After cooling to room temperature, 2-picoline borane (1.82 g, 85%) and 3N aqueous hydrochloric acid solution (12 mL) were added and stirred overnight at room temperature to obtain a reaction mixture. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the resulting reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent: ethyl acetate/heptane) to obtain oily tert-butyl 2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1-carboxylate. (1.68 g) was obtained.
1 H NMR (CDCl 3 /300MHz):δ(ppm) = 7.23-7.18 (m, 1H), 6.90-6.80 (m, 2H), 4.53 (brs, 1H), 3.92 (s, 2H), 2.92 (s , 3H), 2.42 (s, 3H), 1.49 (s, 9H).
(1)4-フルオロ-2-メチルベンズアルデヒド(1.0g)と1-Boc-1-メチルヒドラジン(1.06g)のエタノール(35mL)溶液を75℃で3時間撹拌した。室温に冷却後、2-ピコリンボラン(1.82g、85%)および3N 塩酸水溶液(12mL)を加え、室温で一晩撹拌し反応混合液を得た。前記反応混合液に飽和炭酸水素ナトリウム水溶液を加え得られた反応混合物を、減圧下濃縮した。残渣に酢酸エチルを加え、水層を酢酸エチルで抽出した。抽出により得られた有機層を水、飽和食塩水で順次洗浄し、無水硫酸ナトリウムで乾燥、ろ過したあと、減圧下濃縮した。得られた残渣をカラムクロマトグラフィー(溶離液:酢酸エチル/ヘプタン)で精製して、油状のtert-ブチル 2-(4-フルオロ-2-メチルベンジル)-1-メチルヒドラジン-1-カルボキシレ-ト(1.68g)を得た。
1H NMR (CDCl3/300MHz):δ(ppm) = 7.23-7.18 (m, 1H), 6.90-6.80 (m, 2H), 4.53 (brs, 1H), 3.92 (s, 2H), 2.92 (s, 3H), 2.42 (s, 3H), 1.49 (s, 9H). Synthesis Example 2: Synthesis of 2-amino-4-chloro-N-(4-fluoro-2-methylbenzyl)-N'-methylthiazole-5-carbohydrazide (compound No. 105) (1) 4-fluoro- A solution of 2-methylbenzaldehyde (1.0 g) and 1-Boc-1-methylhydrazine (1.06 g) in ethanol (35 mL) was stirred at 75° C. for 3 hours. After cooling to room temperature, 2-picoline borane (1.82 g, 85%) and 3N aqueous hydrochloric acid solution (12 mL) were added and stirred overnight at room temperature to obtain a reaction mixture. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the resulting reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent: ethyl acetate/heptane) to obtain oily tert-butyl 2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1-carboxylate. (1.68 g) was obtained.
1 H NMR (CDCl 3 /300MHz):δ(ppm) = 7.23-7.18 (m, 1H), 6.90-6.80 (m, 2H), 4.53 (brs, 1H), 3.92 (s, 2H), 2.92 (s , 3H), 2.42 (s, 3H), 1.49 (s, 9H).
(2)2-[(tert-ブトキシカルボニル)アミノ]-4-クロロチアゾール-5-カルボン酸(230mg)のテトラヒドロフラン(10mL)溶液に、オキサリルクロリド(0.1mL)、N,N-ジメチルホルムアミド(4mg)を0℃で加えて、窒素雰囲気下で撹拌した。反応温度を10分後に室温、さらに30分後に45℃へと順次昇温した。計1.5時間撹拌した後、室温に冷却し反応混合物を得た。前記反応混合物を減圧下濃縮し、カルボン酸クロライドを得た。tert-ブチル 2-(4-フルオロ-2-メチルベンジル)-1-メチルヒドラジン-1-カルボキシレート(150mg)のテトラヒドロフラン(5mL)溶液に水素化ナトリウム(23mg、60%)を0℃で加えた。15分間撹拌したのち、カルボン酸クロライドのテトラヒドロフラン(5mL)溶液を加え、窒素雰囲気下、75℃で3時間撹拌し反応混合物を得た。前記反応混合物を室温へ放冷した後、水、酢酸エチルを加えて、水層を酢酸エチルで抽出した。抽出により得られた有機層を水、飽和食塩水で順次洗浄し、無水硫酸ナトリウムで乾燥、ろ過した後、減圧下濃縮した。得られた残渣をカラムクロマトグラフィー(溶離液:酢酸エチル/ヘプタン)で精製して、油状のtert-ブチル 2-{2-[(tert-ブトキシカルボニル)アミノ]-4-クロロチアゾール-5-カルボニル}-2-(4-フルオロ-2-メチルベンジル)-1-メチルヒドラジン-1-カルボキシレート(248mg)を得た。
1H NMR (DMSO-d6/300MHz):δ(ppm) = 12.06 (s, 1H), 7.31-7.26 (m, 1H), 7.11-6.98 (m、2H), 5.04-5.00 (m, 1H), 4.69-4.51 (1H, m), 2.92 (brs, 2H), 2.73 (brs, 1H), 2.33 (s, 3H), 1.34-1.09 (m, 18H). (2) Oxalyl chloride (0.1 mL), N,N-dimethylformamide ( 4 mg) was added at 0° C. and stirred under nitrogen atmosphere. The reaction temperature was raised sequentially to room temperature after 10 minutes and to 45°C after further 30 minutes. After stirring for a total of 1.5 hours, the mixture was cooled to room temperature to obtain a reaction mixture. The reaction mixture was concentrated under reduced pressure to obtain carboxylic acid chloride. Sodium hydride (23 mg, 60%) was added to a solution of tert-butyl 2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1-carboxylate (150 mg) in tetrahydrofuran (5 mL) at 0°C. . After stirring for 15 minutes, a solution of carboxylic acid chloride in tetrahydrofuran (5 mL) was added, and the mixture was stirred at 75° C. for 3 hours under a nitrogen atmosphere to obtain a reaction mixture. After the reaction mixture was allowed to cool to room temperature, water and ethyl acetate were added, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate/heptane) to give oily tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carbonyl. }-2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1-carboxylate (248 mg) was obtained.
1 H NMR (DMSO-d 6 /300MHz): δ(ppm) = 12.06 (s, 1H), 7.31-7.26 (m, 1H), 7.11-6.98 (m, 2H), 5.04-5.00 (m, 1H) , 4.69-4.51 (1H, m), 2.92 (brs, 2H), 2.73 (brs, 1H), 2.33 (s, 3H), 1.34-1.09 (m, 18H).
1H NMR (DMSO-d6/300MHz):δ(ppm) = 12.06 (s, 1H), 7.31-7.26 (m, 1H), 7.11-6.98 (m、2H), 5.04-5.00 (m, 1H), 4.69-4.51 (1H, m), 2.92 (brs, 2H), 2.73 (brs, 1H), 2.33 (s, 3H), 1.34-1.09 (m, 18H). (2) Oxalyl chloride (0.1 mL), N,N-dimethylformamide ( 4 mg) was added at 0° C. and stirred under nitrogen atmosphere. The reaction temperature was raised sequentially to room temperature after 10 minutes and to 45°C after further 30 minutes. After stirring for a total of 1.5 hours, the mixture was cooled to room temperature to obtain a reaction mixture. The reaction mixture was concentrated under reduced pressure to obtain carboxylic acid chloride. Sodium hydride (23 mg, 60%) was added to a solution of tert-butyl 2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1-carboxylate (150 mg) in tetrahydrofuran (5 mL) at 0°C. . After stirring for 15 minutes, a solution of carboxylic acid chloride in tetrahydrofuran (5 mL) was added, and the mixture was stirred at 75° C. for 3 hours under a nitrogen atmosphere to obtain a reaction mixture. After the reaction mixture was allowed to cool to room temperature, water and ethyl acetate were added, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained by extraction was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate/heptane) to give oily tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carbonyl. }-2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1-carboxylate (248 mg) was obtained.
1 H NMR (DMSO-d 6 /300MHz): δ(ppm) = 12.06 (s, 1H), 7.31-7.26 (m, 1H), 7.11-6.98 (m, 2H), 5.04-5.00 (m, 1H) , 4.69-4.51 (1H, m), 2.92 (brs, 2H), 2.73 (brs, 1H), 2.33 (s, 3H), 1.34-1.09 (m, 18H).
(3)tert-ブチル 2-{2-[(tert-ブトキシカルボニル)アミノ]-4-クロロチアゾール-5-カルボニル}-2-(4-フルオロ-2-メチルベンジル)-1-メチルヒドラジン-1-カルボキシレート(248mg)と2,6-ジメチルピリジン(0.55mL)のジクロロメタン(5mL)溶液にトリフルオロメタンスルホン酸トリメチルシリル(0.68mL)を室温で加え、加熱還流下で一晩撹拌し反応混合物を得た。反応終了後、前記反応混合物を室温まで放冷した後、飽和塩化アンモニウム水溶液を加えた。さらに、酢酸エチルを加え、抽出した。抽出により得られた有機層を飽和炭酸水素ナトリウム水溶液、水と飽和食塩水で順次洗浄し、無水硫酸ナトリウムで乾燥、ろ過した後、減圧下濃縮した。得られた残渣をカラムクロマトグラフィー(溶離液:酢酸エチル/ヘプタン)で精製して、固体の目的物(108mg)を得た。
1H NMR (DMSO-d6/300MHz):δ(ppm) = 7.61 (brs, 2H), 7.15 (dd, 1H), 7.07-6.97 (m, 2H), 5.05 (q, 1H), 4.69 (s, 2H), 2.40 (d, 3H), 2.28 (s, 3H). (3) tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carbonyl}-2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1 - To a solution of carboxylate (248 mg) and 2,6-dimethylpyridine (0.55 mL) in dichloromethane (5 mL) was added trimethylsilyl trifluoromethanesulfonate (0.68 mL) at room temperature, and the reaction mixture was stirred overnight under heating under reflux. I got it. After the reaction was completed, the reaction mixture was allowed to cool to room temperature, and then a saturated aqueous ammonium chloride solution was added. Furthermore, ethyl acetate was added for extraction. The organic layer obtained by the extraction was washed successively with a saturated aqueous sodium bicarbonate solution, water, and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent: ethyl acetate/heptane) to obtain the target product (108 mg) as a solid.
1 H NMR (DMSO-d 6 /300MHz): δ(ppm) = 7.61 (brs, 2H), 7.15 (dd, 1H), 7.07-6.97 (m, 2H), 5.05 (q, 1H), 4.69 (s , 2H), 2.40 (d, 3H), 2.28 (s, 3H).
1H NMR (DMSO-d6/300MHz):δ(ppm) = 7.61 (brs, 2H), 7.15 (dd, 1H), 7.07-6.97 (m, 2H), 5.05 (q, 1H), 4.69 (s, 2H), 2.40 (d, 3H), 2.28 (s, 3H). (3) tert-butyl 2-{2-[(tert-butoxycarbonyl)amino]-4-chlorothiazole-5-carbonyl}-2-(4-fluoro-2-methylbenzyl)-1-methylhydrazine-1 - To a solution of carboxylate (248 mg) and 2,6-dimethylpyridine (0.55 mL) in dichloromethane (5 mL) was added trimethylsilyl trifluoromethanesulfonate (0.68 mL) at room temperature, and the reaction mixture was stirred overnight under heating under reflux. I got it. After the reaction was completed, the reaction mixture was allowed to cool to room temperature, and then a saturated aqueous ammonium chloride solution was added. Furthermore, ethyl acetate was added for extraction. The organic layer obtained by the extraction was washed successively with a saturated aqueous sodium bicarbonate solution, water, and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent: ethyl acetate/heptane) to obtain the target product (108 mg) as a solid.
1 H NMR (DMSO-d 6 /300MHz): δ(ppm) = 7.61 (brs, 2H), 7.15 (dd, 1H), 7.07-6.97 (m, 2H), 5.05 (q, 1H), 4.69 (s , 2H), 2.40 (d, 3H), 2.28 (s, 3H).
次に、化合物(I)の代表例を第1表に具体的に挙げる。これらの化合物は前記製造方法及び前記合成例、並びに本技術分野において公知の方法に基づいて合成することができる。
表中、No.は化合物No.を示す。第1表の物性欄にNMRと記載した化合物は第2表に1H-NMRスペクトラムデータを示す。第1表中のR2、R3、R4欄で用いた略語は、各々以下の置換基を示す。Meはメチル基、Etはエチル基、n‐Prはノルマルプロピル基、i‐Prはイソプロピル基、c‐Prはシクロプロピル基、i-Buはイソブチル基、c-Buはシクロブチル基、c-Pentylはシクロペンチル基、c-Hexylはシクロへキシル基、CNはシアノ基、NO2はニトロ基、diは2個、triは3個、及びtetraは4個である。
また、化合物(I)の塩である場合は、第1表中の物性欄にその塩の種類を示す。例えば、第1表中の物性欄に、HCl塩と記載した化合物は塩酸塩、TsOH塩と記載した化合物はパラトルエンスルホン酸塩、Na塩と記載した化合物はナトリウム塩である。例えば化合物No.254は化合物No.1の塩酸塩、化合物No.255は化合物No.76の塩酸塩、及び化合物No.256は化合物No.78の塩酸塩である。化合物No.257は化合物No.1のパラトルエンスルホン酸塩、化合物No.258は化合物No.76のパラトルエンスルホン酸塩、及び化合物No.259は化合物No.78のパラトルエンスルホン酸塩である。化合物No.524は化合物No.523のナトリウム塩である。 Next, representative examples of compound (I) are specifically listed in Table 1. These compounds can be synthesized based on the above production method, the above synthesis example, and methods known in the technical field.
In the table, No. is compound No. shows. For compounds described as NMR in the physical properties column of Table 1, 1 H-NMR spectrum data are shown in Table 2. The abbreviations used in the R 2 , R 3 , and R 4 columns in Table 1 each represent the following substituents. Me is a methyl group, Et is an ethyl group, n-Pr is a normal propyl group, i-Pr is an isopropyl group, c-Pr is a cyclopropyl group, i-Bu is an isobutyl group, c-Bu is a cyclobutyl group, c-Pentyl is a cyclopentyl group, c-Hexyl is a cyclohexyl group, CN is a cyano group, NO 2 is a nitro group, di is 2, tri is 3, and tetra is 4.
In addition, in the case of a salt of compound (I), the type of the salt is shown in the physical properties column of Table 1. For example, in the physical properties column of Table 1, a compound described as HCl salt is a hydrochloride, a compound described as TsOH salt is a para-toluenesulfonate, and a compound described as Na salt is a sodium salt. For example, compound no. 254 is compound no. 1 hydrochloride, compound no. 255 is compound no. 76 hydrochloride, and compound no. 256 is compound no. 78 hydrochloride. Compound no. 257 is compound no. para-toluene sulfonate of Compound No. 1, Compound No. 258 is compound no. 76 para-toluene sulfonate, and compound no. 259 is compound no. 78 para-toluenesulfonate. Compound no. 524 is compound no. It is the sodium salt of 523.
表中、No.は化合物No.を示す。第1表の物性欄にNMRと記載した化合物は第2表に1H-NMRスペクトラムデータを示す。第1表中のR2、R3、R4欄で用いた略語は、各々以下の置換基を示す。Meはメチル基、Etはエチル基、n‐Prはノルマルプロピル基、i‐Prはイソプロピル基、c‐Prはシクロプロピル基、i-Buはイソブチル基、c-Buはシクロブチル基、c-Pentylはシクロペンチル基、c-Hexylはシクロへキシル基、CNはシアノ基、NO2はニトロ基、diは2個、triは3個、及びtetraは4個である。
また、化合物(I)の塩である場合は、第1表中の物性欄にその塩の種類を示す。例えば、第1表中の物性欄に、HCl塩と記載した化合物は塩酸塩、TsOH塩と記載した化合物はパラトルエンスルホン酸塩、Na塩と記載した化合物はナトリウム塩である。例えば化合物No.254は化合物No.1の塩酸塩、化合物No.255は化合物No.76の塩酸塩、及び化合物No.256は化合物No.78の塩酸塩である。化合物No.257は化合物No.1のパラトルエンスルホン酸塩、化合物No.258は化合物No.76のパラトルエンスルホン酸塩、及び化合物No.259は化合物No.78のパラトルエンスルホン酸塩である。化合物No.524は化合物No.523のナトリウム塩である。 Next, representative examples of compound (I) are specifically listed in Table 1. These compounds can be synthesized based on the above production method, the above synthesis example, and methods known in the technical field.
In the table, No. is compound No. shows. For compounds described as NMR in the physical properties column of Table 1, 1 H-NMR spectrum data are shown in Table 2. The abbreviations used in the R 2 , R 3 , and R 4 columns in Table 1 each represent the following substituents. Me is a methyl group, Et is an ethyl group, n-Pr is a normal propyl group, i-Pr is an isopropyl group, c-Pr is a cyclopropyl group, i-Bu is an isobutyl group, c-Bu is a cyclobutyl group, c-Pentyl is a cyclopentyl group, c-Hexyl is a cyclohexyl group, CN is a cyano group, NO 2 is a nitro group, di is 2, tri is 3, and tetra is 4.
In addition, in the case of a salt of compound (I), the type of the salt is shown in the physical properties column of Table 1. For example, in the physical properties column of Table 1, a compound described as HCl salt is a hydrochloride, a compound described as TsOH salt is a para-toluenesulfonate, and a compound described as Na salt is a sodium salt. For example, compound no. 254 is compound no. 1 hydrochloride, compound no. 255 is compound no. 76 hydrochloride, and compound no. 256 is compound no. 78 hydrochloride. Compound no. 257 is compound no. para-toluene sulfonate of Compound No. 1, Compound No. 258 is compound no. 76 para-toluene sulfonate, and compound no. 259 is compound no. 78 para-toluenesulfonate. Compound no. 524 is compound no. It is the sodium salt of 523.
第2表中の1H-NMRスペクトラムデータのsはシングレット(一重線)、brsはブロードしたシングレット、dはダブレット(二重線)、tはトリプレット(三重線)、qはカルテット(四重線)、sextはセクテット(六重線)、sepはセプテット(七重線)、mはマルチプレット(多重線)である。
In the 1H -NMR spectrum data in Table 2, s is a singlet, brs is a broad singlet, d is a doublet, t is a triplet, and q is a quartet. ), sext is a sextet, sep is a septet, and m is a multiplet.
第1表中のR4欄で示す置換基の位置は以下の通りの置換基の位置を示す。
The positions of the substituents shown in the R4 column in Table 1 indicate the positions of the substituents as follows.
1H-NMRスペクトラムデータ〔1H-核磁気共鳴分光法にて測定;δは化学シフト値(ppm)である〕を第2表に示す。
1 H-NMR spectrum data [measured by 1 H-nuclear magnetic resonance spectroscopy; δ is the chemical shift value (ppm)] is shown in Table 2.
[試験例]
化合物(I)を含む薬液の調製:
化合物(I)とアセトン又はジメチルスルホキシドとを混合し、化合物(I)を溶解させた。化合物(I)の溶液に水を加えて、有効成分である化合物(I)が所定の濃度(400ppm、200ppm又は100ppm)になるように希釈して薬液を得た。この薬液を、以下の試験例1~試験例3にて利用した。 [Test example]
Preparation of drug solution containing compound (I):
Compound (I) and acetone or dimethyl sulfoxide were mixed to dissolve compound (I). Water was added to the solution of Compound (I) to dilute the active ingredient Compound (I) to a predetermined concentration (400 ppm, 200 ppm or 100 ppm) to obtain a drug solution. This chemical solution was used in Test Examples 1 to 3 below.
化合物(I)を含む薬液の調製:
化合物(I)とアセトン又はジメチルスルホキシドとを混合し、化合物(I)を溶解させた。化合物(I)の溶液に水を加えて、有効成分である化合物(I)が所定の濃度(400ppm、200ppm又は100ppm)になるように希釈して薬液を得た。この薬液を、以下の試験例1~試験例3にて利用した。 [Test example]
Preparation of drug solution containing compound (I):
Compound (I) and acetone or dimethyl sulfoxide were mixed to dissolve compound (I). Water was added to the solution of Compound (I) to dilute the active ingredient Compound (I) to a predetermined concentration (400 ppm, 200 ppm or 100 ppm) to obtain a drug solution. This chemical solution was used in Test Examples 1 to 3 below.
試験例1:トマト疫病(Phytophthora infestans)に対する殺菌効果試験(予防効果試験)
直径6cmのビニールポットでトマトを栽培し、4.5~5.5葉期に達した時に薬液10mlをスプレーガンにて散布した。薬液が乾燥した後(処理当日)に、トマト疫病菌(Phytophthora infestans)の胞子懸濁液を噴霧接種し、温度20℃、湿度95%以上の接種箱に16時間入れた。その後、20℃の恒温室内に置き、接種3日後に病斑面積率を調査し、下記計算式に従って防除率を算出した。その結果、以下の化合物を含む各組成物(有効成分濃度は400ppm又は200ppm)がトマト疫病に対して90%以上の防除率を示した。なお、化合物No.35、160、178、及び179は有効成分濃度200ppmでトマト疫病に対して90%以上の防除率を示したものであり、それ以外の化合物は有効成分濃度400ppmでトマト疫病に対して90%以上の防除率を示したものである。
[防除率の計算式]
防除率(%)=100―(X/Y)×100
X:供試化合物の病斑面積率(%)、Y:無処理区の病斑面積率(%)
化合物:No.1、2、3、4、5、6、7、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、30、31、32、33、34、35、39、40、41、42、43、45、46、47、48、49、50、51、53、54、55、56、57、58、59、60、62、64、65、66、67、68、70、71、72、73、74、76、77、78、79、81、83、84、85、86、87、88、89、90、91、92、93、95、96、97、98、99、101、102、103、104、105、106、107、108、111、112、113、114、115、117、119、120、121、122、123、124、125、126、127、128、130、132、133、134、135、136、137、138、139、140、141、142、143、144、145、148、149、150、151、152、153、154、155、156、157、158、159、160、163、164、165、166、167、170、171、172、173、174、175、177、178、179、180、181、182、184、185、186、188、189、190、191、192、193、194、195、196、198、199、200、201、202、203、204、205、206、207、208、209、210、211、212、213、214、215、217、218、221、228、229、233、234、235、238、241、243、246、249、250、260、261、262、263、264、265、267、268、269、270、271、272、273、274、275、276、277、278、279、280、281、282、283、284、285、286、287、288、289、290、291、292、293、294、295、296、297、298、299、300、301、302、303、304、305、306、307、308、309、310、311、312、313、314、315、316、317、319、320、321、323、324、325、326、329、331、332、333、334、335、336、337、338、339、340、341、342、343、345、346、347、348、349、350、351、352、355、356、357、358、359、360、361、362、363、364、365、366、367、368、369、371、372、373、374、375、376、378、379、380、381、382、383、390、392、393、394、395、396、397、398、399、400、401、402、403、405、406、408、409、411、412、413、414、415、416、417、418、419、420、421、422、423、424、426、427、428、429、430、431、433、435、436、437、438、440、441、442、443、444、445、446、447、449、452、453、454、455、456、457、458、459、460、461、463、464、465、466、467、468、469、470、472、473、474、475、476、477、478、479、480、481、482、483、484、485、486、487、488、489、490、491、492、493、494、496、497、499、501、503、504、505、506、507、508、509、510、511、512、514、515、516、517、518、519、520、521、522、523、524、525、526、527、528、529、530、532、533、534、535、536、537及び538
また、以下の化合物を含む各組成物(有効成分濃度は100ppm)がトマト疫病に対して90%以上の防除率を示した。
化合物:No.1、2、3、4、5、6、7、8、9、10、11、13、14、15、16、17、18、19、20、21、22、23、24、25、27、30、31、32、33、34、35、36、37、38、39、40、41、44、48、50、51、54、55、56、57、58、60、61、62、64、65、66、67、68、70、71、72、73、75、76、77、78、79、81、83、84、85、86、87、88、89、90、91、92、93、95、96、97、98、99、101、102、103、104、105、106、107、108、111、112、113、114、115、116、117、119、120、121、122、123、124、125、126、127、128、130、132、133、134、135、136、137、138、139、140、141、142、143、144、145、146、148、149、150、151、152、153、154、155、156、157、158、159、160、163、164、165、166、167、170、171、172、173、174、175、177、178、180、181、182、184、185、186、188、189、190、191、192、193、194、195、196、199、201、202、203、204、205、206、207、208、209、210、211、212、213、214、215、217、218、221、228、229、233、234、235、238、241、243、246、249、260、261、262、263、264、265、267、268、270、271、272、273、274、275、276、277、278、279、280、282、283、284、285、286、287、288、289、290、291、292、293、294、295、296、297、298、299、300、301、302、303、304、305、306、307、308、309、310、311、312、313、314、315、316、317、319、321、323、324、325、326、329、331、332、333、334、335、336、338、339、340、341、342、343、345、346、347、348、349、350、351、355、356、357、358、359、360、361、362、363、364、365、367、368、369、371、372、373、374、375、378、379、380、381、382、383、390、392、393、395、396、397、398、399、400、401、402、403、405、406、408、409、411、412、413、414、415、416、417、418、419、420、422、423、424、426、427、428、429、430、433、435、436、437、438、440、441、442、443、444、445、446、447、449、450、452、453、454、455、456、458、459、461、463、464、465、467、468、469、470、472、474、475、476、477、478、479、480、481、482、483、484、485、486、487、488、489、490、491、492、494、496、497、499、501、503、505、507、508、509、510、511、512、515、517、518、519、520、521、522、523、525、527、528、530、532、533、534、535、536、537及び538 Test Example 1: Bactericidal effect test against tomato late blight (Phytophthora infestans) (preventive effect test)
Tomatoes were grown in vinyl pots with a diameter of 6 cm, and when they reached the 4.5 to 5.5 leaf stage, 10 ml of the chemical solution was sprayed with a spray gun. After the chemical solution dried (on the day of treatment), a spore suspension of Phytophthora infestans was spray inoculated and placed in an inoculation box at a temperature of 20° C. and a humidity of 95% or higher for 16 hours. Thereafter, the plants were placed in a constant temperature room at 20° C., and the lesion area ratio was investigated 3 days after inoculation, and the control rate was calculated according to the following formula. As a result, each composition containing the following compounds (active ingredient concentration: 400 ppm or 200 ppm) showed a control rate of 90% or more against tomato late blight. In addition, compounds No. 35, 160, 178, and 179 showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 200 ppm, and the other compounds showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 400 ppm. This shows a control rate of 90% or more.
[Formula for calculating control rate]
Control rate (%) = 100 - (X/Y) x 100
X: Lesion area rate of test compound (%), Y: Lesion area rate of untreated area (%)
Compounds: No. 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 30, 31, 32, 33, 34, 35, 39, 40, 41, 42, 43, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 62, 64, 65, 66, 67, 68, 70, 71, 72, 73, 74, 76, 77, 78, 79, 81, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 95, 96, 97, 98, 99, 101, 102, 103, 104, 105, 106, 107, 108, 111, 112, 113, 114, 115, 117, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 130, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 163, 164, 165, 166, 167, 170, 171, 172, 173, 174, 175, 177, 178, 179, 180, 181, 182, 184, 185, 186, 188, 189, 190, 191, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 217, 218, 221, 228, 229, 233, 234, 235, 238, 241, 243, 246, 249, 250, 260, 261, 262, 263, 264, 265, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309, 310, 311, 312, 313, 314, 315, 316, 317, 319, 320, 321, 323, 324, 325, 326, 329, 331, 332, 333, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 345, 346, 347, 348, 349, 350, 351, 352, 355, 356, 357, 358, 359, 360, 361, 362, 363, 364, 365, 366, 367, 368, 369, 371, 372, 373, 374, 375, 376, 378, 379, 380, 381, 382, 383, 390, 392, 393, 394, 395, 396, 397, 398, 399, 400, 401, 402, 403, 405, 406, 408, 409, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 421, 422, 423, 424, 426, 427, 428, 429, 430, 431, 433, 435, 436, 437, 438, 440, 441, 442, 443, 444, 445, 446, 447, 449, 452, 453, 454, 455, 456, 457, 458, 459, 460, 461, 463, 464, 465, 466, 467, 468, 469, 470, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 484, 485, 486, 487, 488, 489, 490, 491, 492, 493, 494, 496, 497, 499, 501, 503, 504, 505, 506, 507, 508, 509, 510, 511, 512, 514, 515, 516, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 529, 530, 532, 533, 534, 535, 536, 537 and 538
Furthermore, each composition containing the following compounds (active ingredient concentration: 100 ppm) showed a control rate of 90% or more against tomato late blight.
Compound: No. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 27, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 44, 48, 50, 51, 54, 55, 56, 57, 58, 60, 61, 62, 64, 65, 66, 67, 68, 70, 71, 72, 73, 75, 76, 77, 78, 79, 81, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 95, 96, 97, 98, 99, 101, 102, 103, 104, 105, 106, 107, 108, 111, 112, 113, 114, 115, 116, 117, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 130, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 163, 164, 165, 166, 167, 170, 171, 172, 173, 174, 175, 177, 178, 180, 181, 182, 184, 185, 186, 188, 189, 190, 191, 192, 193, 194, 195, 196, 199, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 217, 218, 221, 228, 229, 233, 234, 235, 238, 241, 243, 246, 249, 260, 261, 262, 263, 264, 265, 267, 268, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309, 310, 311, 312, 313, 314, 315, 316, 317, 319, 321, 323, 324, 325, 326, 329, 331, 332, 333, 334, 335, 336, 338, 339, 340, 341, 342, 343, 345, 346, 347, 348, 349, 350, 351, 355, 356, 357, 358, 359, 360, 361, 362, 363, 364, 365, 367, 368, 369, 371, 372, 373, 374, 375, 378, 379, 380, 381, 382, 383, 390, 392, 393, 395, 396, 397, 398, 399, 400, 401, 402, 403, 405, 406, 408, 409, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 422, 423, 424, 426, 427, 428, 429, 430, 433, 435, 436, 437, 438, 440, 441, 442, 443, 444, 445, 446, 447, 449, 450, 452, 453, 454, 455, 456, 458, 459, 461, 463, 464, 465, 467, 468, 469, 470, 472, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 484, 485, 486, 487, 488, 489, 490, 491, 492, 494, 496, 497, 499, 501, 503, 505, 507, 508, 509, 510, 511, 512, 515, 517, 518, 519, 520, 521, 522, 523, 525, 527, 528, 530, 532, 533, 534, 535, 536, 537 and 538
直径6cmのビニールポットでトマトを栽培し、4.5~5.5葉期に達した時に薬液10mlをスプレーガンにて散布した。薬液が乾燥した後(処理当日)に、トマト疫病菌(Phytophthora infestans)の胞子懸濁液を噴霧接種し、温度20℃、湿度95%以上の接種箱に16時間入れた。その後、20℃の恒温室内に置き、接種3日後に病斑面積率を調査し、下記計算式に従って防除率を算出した。その結果、以下の化合物を含む各組成物(有効成分濃度は400ppm又は200ppm)がトマト疫病に対して90%以上の防除率を示した。なお、化合物No.35、160、178、及び179は有効成分濃度200ppmでトマト疫病に対して90%以上の防除率を示したものであり、それ以外の化合物は有効成分濃度400ppmでトマト疫病に対して90%以上の防除率を示したものである。
[防除率の計算式]
防除率(%)=100―(X/Y)×100
X:供試化合物の病斑面積率(%)、Y:無処理区の病斑面積率(%)
化合物:No.1、2、3、4、5、6、7、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、30、31、32、33、34、35、39、40、41、42、43、45、46、47、48、49、50、51、53、54、55、56、57、58、59、60、62、64、65、66、67、68、70、71、72、73、74、76、77、78、79、81、83、84、85、86、87、88、89、90、91、92、93、95、96、97、98、99、101、102、103、104、105、106、107、108、111、112、113、114、115、117、119、120、121、122、123、124、125、126、127、128、130、132、133、134、135、136、137、138、139、140、141、142、143、144、145、148、149、150、151、152、153、154、155、156、157、158、159、160、163、164、165、166、167、170、171、172、173、174、175、177、178、179、180、181、182、184、185、186、188、189、190、191、192、193、194、195、196、198、199、200、201、202、203、204、205、206、207、208、209、210、211、212、213、214、215、217、218、221、228、229、233、234、235、238、241、243、246、249、250、260、261、262、263、264、265、267、268、269、270、271、272、273、274、275、276、277、278、279、280、281、282、283、284、285、286、287、288、289、290、291、292、293、294、295、296、297、298、299、300、301、302、303、304、305、306、307、308、309、310、311、312、313、314、315、316、317、319、320、321、323、324、325、326、329、331、332、333、334、335、336、337、338、339、340、341、342、343、345、346、347、348、349、350、351、352、355、356、357、358、359、360、361、362、363、364、365、366、367、368、369、371、372、373、374、375、376、378、379、380、381、382、383、390、392、393、394、395、396、397、398、399、400、401、402、403、405、406、408、409、411、412、413、414、415、416、417、418、419、420、421、422、423、424、426、427、428、429、430、431、433、435、436、437、438、440、441、442、443、444、445、446、447、449、452、453、454、455、456、457、458、459、460、461、463、464、465、466、467、468、469、470、472、473、474、475、476、477、478、479、480、481、482、483、484、485、486、487、488、489、490、491、492、493、494、496、497、499、501、503、504、505、506、507、508、509、510、511、512、514、515、516、517、518、519、520、521、522、523、524、525、526、527、528、529、530、532、533、534、535、536、537及び538
また、以下の化合物を含む各組成物(有効成分濃度は100ppm)がトマト疫病に対して90%以上の防除率を示した。
化合物:No.1、2、3、4、5、6、7、8、9、10、11、13、14、15、16、17、18、19、20、21、22、23、24、25、27、30、31、32、33、34、35、36、37、38、39、40、41、44、48、50、51、54、55、56、57、58、60、61、62、64、65、66、67、68、70、71、72、73、75、76、77、78、79、81、83、84、85、86、87、88、89、90、91、92、93、95、96、97、98、99、101、102、103、104、105、106、107、108、111、112、113、114、115、116、117、119、120、121、122、123、124、125、126、127、128、130、132、133、134、135、136、137、138、139、140、141、142、143、144、145、146、148、149、150、151、152、153、154、155、156、157、158、159、160、163、164、165、166、167、170、171、172、173、174、175、177、178、180、181、182、184、185、186、188、189、190、191、192、193、194、195、196、199、201、202、203、204、205、206、207、208、209、210、211、212、213、214、215、217、218、221、228、229、233、234、235、238、241、243、246、249、260、261、262、263、264、265、267、268、270、271、272、273、274、275、276、277、278、279、280、282、283、284、285、286、287、288、289、290、291、292、293、294、295、296、297、298、299、300、301、302、303、304、305、306、307、308、309、310、311、312、313、314、315、316、317、319、321、323、324、325、326、329、331、332、333、334、335、336、338、339、340、341、342、343、345、346、347、348、349、350、351、355、356、357、358、359、360、361、362、363、364、365、367、368、369、371、372、373、374、375、378、379、380、381、382、383、390、392、393、395、396、397、398、399、400、401、402、403、405、406、408、409、411、412、413、414、415、416、417、418、419、420、422、423、424、426、427、428、429、430、433、435、436、437、438、440、441、442、443、444、445、446、447、449、450、452、453、454、455、456、458、459、461、463、464、465、467、468、469、470、472、474、475、476、477、478、479、480、481、482、483、484、485、486、487、488、489、490、491、492、494、496、497、499、501、503、505、507、508、509、510、511、512、515、517、518、519、520、521、522、523、525、527、528、530、532、533、534、535、536、537及び538 Test Example 1: Bactericidal effect test against tomato late blight (Phytophthora infestans) (preventive effect test)
Tomatoes were grown in vinyl pots with a diameter of 6 cm, and when they reached the 4.5 to 5.5 leaf stage, 10 ml of the chemical solution was sprayed with a spray gun. After the chemical solution dried (on the day of treatment), a spore suspension of Phytophthora infestans was spray inoculated and placed in an inoculation box at a temperature of 20° C. and a humidity of 95% or higher for 16 hours. Thereafter, the plants were placed in a constant temperature room at 20° C., and the lesion area ratio was investigated 3 days after inoculation, and the control rate was calculated according to the following formula. As a result, each composition containing the following compounds (active ingredient concentration: 400 ppm or 200 ppm) showed a control rate of 90% or more against tomato late blight. In addition, compounds No. 35, 160, 178, and 179 showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 200 ppm, and the other compounds showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 400 ppm. This shows a control rate of 90% or more.
[Formula for calculating control rate]
Control rate (%) = 100 - (X/Y) x 100
X: Lesion area rate of test compound (%), Y: Lesion area rate of untreated area (%)
Compounds: No. 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 30, 31, 32, 33, 34, 35, 39, 40, 41, 42, 43, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 62, 64, 65, 66, 67, 68, 70, 71, 72, 73, 74, 76, 77, 78, 79, 81, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 95, 96, 97, 98, 99, 101, 102, 103, 104, 105, 106, 107, 108, 111, 112, 113, 114, 115, 117, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 130, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 163, 164, 165, 166, 167, 170, 171, 172, 173, 174, 175, 177, 178, 179, 180, 181, 182, 184, 185, 186, 188, 189, 190, 191, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 217, 218, 221, 228, 229, 233, 234, 235, 238, 241, 243, 246, 249, 250, 260, 261, 262, 263, 264, 265, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309, 310, 311, 312, 313, 314, 315, 316, 317, 319, 320, 321, 323, 324, 325, 326, 329, 331, 332, 333, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 345, 346, 347, 348, 349, 350, 351, 352, 355, 356, 357, 358, 359, 360, 361, 362, 363, 364, 365, 366, 367, 368, 369, 371, 372, 373, 374, 375, 376, 378, 379, 380, 381, 382, 383, 390, 392, 393, 394, 395, 396, 397, 398, 399, 400, 401, 402, 403, 405, 406, 408, 409, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 421, 422, 423, 424, 426, 427, 428, 429, 430, 431, 433, 435, 436, 437, 438, 440, 441, 442, 443, 444, 445, 446, 447, 449, 452, 453, 454, 455, 456, 457, 458, 459, 460, 461, 463, 464, 465, 466, 467, 468, 469, 470, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 484, 485, 486, 487, 488, 489, 490, 491, 492, 493, 494, 496, 497, 499, 501, 503, 504, 505, 506, 507, 508, 509, 510, 511, 512, 514, 515, 516, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 529, 530, 532, 533, 534, 535, 536, 537 and 538
Furthermore, each composition containing the following compounds (active ingredient concentration: 100 ppm) showed a control rate of 90% or more against tomato late blight.
Compound: No. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 27, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 44, 48, 50, 51, 54, 55, 56, 57, 58, 60, 61, 62, 64, 65, 66, 67, 68, 70, 71, 72, 73, 75, 76, 77, 78, 79, 81, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 95, 96, 97, 98, 99, 101, 102, 103, 104, 105, 106, 107, 108, 111, 112, 113, 114, 115, 116, 117, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 130, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 163, 164, 165, 166, 167, 170, 171, 172, 173, 174, 175, 177, 178, 180, 181, 182, 184, 185, 186, 188, 189, 190, 191, 192, 193, 194, 195, 196, 199, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 217, 218, 221, 228, 229, 233, 234, 235, 238, 241, 243, 246, 249, 260, 261, 262, 263, 264, 265, 267, 268, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309, 310, 311, 312, 313, 314, 315, 316, 317, 319, 321, 323, 324, 325, 326, 329, 331, 332, 333, 334, 335, 336, 338, 339, 340, 341, 342, 343, 345, 346, 347, 348, 349, 350, 351, 355, 356, 357, 358, 359, 360, 361, 362, 363, 364, 365, 367, 368, 369, 371, 372, 373, 374, 375, 378, 379, 380, 381, 382, 383, 390, 392, 393, 395, 396, 397, 398, 399, 400, 401, 402, 403, 405, 406, 408, 409, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 422, 423, 424, 426, 427, 428, 429, 430, 433, 435, 436, 437, 438, 440, 441, 442, 443, 444, 445, 446, 447, 449, 450, 452, 453, 454, 455, 456, 458, 459, 461, 463, 464, 465, 467, 468, 469, 470, 472, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 484, 485, 486, 487, 488, 489, 490, 491, 492, 494, 496, 497, 499, 501, 503, 505, 507, 508, 509, 510, 511, 512, 515, 517, 518, 519, 520, 521, 522, 523, 525, 527, 528, 530, 532, 533, 534, 535, 536, 537 and 538
試験例2:キュウリべと病(Pseudoperonospora cubensis)に対する殺菌効果試験(予防効果試験)
直径6cmのビニールポットでキュウリを栽培し、1.2~1.5葉期に達した時に薬液10mlをスプレーガンにて散布した。薬液が乾燥した後(処理当日)に、キュウリべと病菌(Pseudoperonospora cubensis)の胞子懸濁液を噴霧接種し、温度20℃、湿度95%以上の接種箱に24時間入れた。その後、20℃の恒温室内に置き、接種7日後に病斑面積率を調査し、上記試験例1と同じ計算式により防除率を算出した。その結果、以下の化合物を含む各組成物(有効成分濃度が400ppm)がキュウリべと病に対して90%以上の防除率を示した。
化合物:No.1、2、3、4、5、6、7、9、10、11、13、14、15、17、18、19、20、21、22、23、24、26、27、28、30、31、32、33、34、39、40、41、42、46、47、48、50、51、54、55、56、58、60、62、65、66、67、68、70、71、72、73、76、77、78、79、81、83、84、85、86、87、89、90、92、93、95、96、97、98、99、101、102、103、104、106、111、112、113、114、115、117、119、120、121、122、123、125、126、127、128、130、132、134、135、137、138、139、140、141、142、143、144、148、150、151、152、154、155、157、158、159、164、165、166、167、170、172、173、174、175、177、178、179、180、181、182、183、184、185、186、188、189、190、191、192、193、194、196、199、200、201、202、204、205、206、207、208、209、210、211、212、213、214、215、217、218、221、225、228、229、233、234、235、238、241、242、243、246、263、265、267、268、270、271、272、273、274、276、278、280、282、283、284、285、286、287、288、289、292、293、294、296、297、298、299、300、302、303、305、306、307、308、309、310、311、312、314、316、318、321、323、324、325、326、331、332、333、334、335、336、339、340、341、342、343、345、346、347、348、349、351、352、355、356、357、358、359、360、361、362、363、365、367、368、369、371、372、373、374、375、377、379、380、381、382、383、390、392、393、394、395、396、397、398、400、401、402、403、405、406、408、409、410、411、412、413、414、415、416、417、420、421、422、423、424、426、427、428、429、430、431、433、435、436、437、438、440、441、442、443、444、445、446、449、452、453、454、456、457、458、459、461、463、464、465、466、467、468、469、470、472、474、475、476、477、478、480、482、483、484、485、486、487、488、489、490、491、492、494、497、499、501、503、504、505、506、511、512、517、518、519、520、521、522、523、524、525、526、527、528、530、532、533、534、535、536、537及び538 Test Example 2: Bactericidal effect test against cucumber downy mildew ( Pseudoperonospora cubensis ) (preventive effect test)
Cucumbers were grown in vinyl pots with a diameter of 6 cm, and when they reached the 1.2 to 1.5 leaf stage, 10 ml of the chemical solution was sprayed with a spray gun. After the chemical solution had dried (on the day of treatment), a spore suspension of cucumber downy mildew (Pseudoperonospora cubensis) was spray inoculated and placed in an inoculation box at a temperature of 20° C. and a humidity of 95% or more for 24 hours. Thereafter, the plants were placed in a constant temperature room at 20° C., and the lesion area ratio was investigated 7 days after inoculation, and the control rate was calculated using the same formula as in Test Example 1 above. As a result, each composition (active ingredient concentration: 400 ppm) containing the following compounds showed a control rate of 90% or more against cucumber downy mildew.
Compound: No. 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 13, 14, 15, 17, 18, 19, 20, 21, 22, 23, 24, 26, 27, 28, 30, 31, 32, 33, 34, 39, 40, 41, 42, 46, 47, 48, 50, 51, 54, 55, 56, 58, 60, 62, 65, 66, 67, 68, 70, 71, 72, 73, 76, 77, 78, 79, 81, 83, 84, 85, 86, 87, 89, 90, 92, 93, 95, 96, 97, 98, 99, 101, 102, 103, 104, 106, 111, 112, 113, 114, 115, 117, 119, 120, 121, 122, 123, 125, 126, 127, 128, 130, 132, 134, 135, 137, 138, 139, 140, 141, 142, 143, 144, 148, 150, 151, 152, 154, 155, 157, 158, 159, 164, 165, 166, 167, 170, 172, 173, 174, 175, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186, 188, 189, 190, 191, 192, 193, 194, 196, 199, 200, 201, 202, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 217, 218, 221, 225, 228, 229, 233, 234, 235, 238, 241, 242, 243, 246, 263, 265, 267, 268, 270, 271, 272, 273, 274, 276, 278, 280, 282, 283, 284, 285, 286, 287, 288, 289, 292, 293, 294, 296, 297, 298, 299, 300, 302, 303, 305, 306, 307, 308, 309, 310, 311, 312, 314, 316, 318, 321, 323, 324, 325, 326, 331, 332, 333, 334, 335, 336, 339, 340, 341, 342, 343, 345, 346, 347, 348, 349, 351, 352, 355, 356, 357, 358, 359, 360, 361, 362, 363, 365, 367, 368, 369, 371, 372, 373, 374, 375, 377, 379, 380, 381, 382, 383, 390, 392, 393, 394, 395, 396, 397, 398, 400, 401, 402, 403, 405, 406, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 420, 421, 422, 423, 424, 426, 427, 428, 429, 430, 431, 433, 435, 436, 437, 438, 440, 441, 442, 443, 444, 445, 446, 449, 452, 453, 454, 456, 457, 458, 459, 461, 463, 464, 465, 466, 467, 468, 469, 470, 472, 474, 475, 476, 477, 478, 480, 482, 483, 484, 485, 486, 487, 488, 489, 490, 491, 492, 494, 497, 499, 501, 503, 504, 505, 506, 511, 512, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 530, 532, 533, 534, 535, 536, 537 and 538
直径6cmのビニールポットでキュウリを栽培し、1.2~1.5葉期に達した時に薬液10mlをスプレーガンにて散布した。薬液が乾燥した後(処理当日)に、キュウリべと病菌(Pseudoperonospora cubensis)の胞子懸濁液を噴霧接種し、温度20℃、湿度95%以上の接種箱に24時間入れた。その後、20℃の恒温室内に置き、接種7日後に病斑面積率を調査し、上記試験例1と同じ計算式により防除率を算出した。その結果、以下の化合物を含む各組成物(有効成分濃度が400ppm)がキュウリべと病に対して90%以上の防除率を示した。
化合物:No.1、2、3、4、5、6、7、9、10、11、13、14、15、17、18、19、20、21、22、23、24、26、27、28、30、31、32、33、34、39、40、41、42、46、47、48、50、51、54、55、56、58、60、62、65、66、67、68、70、71、72、73、76、77、78、79、81、83、84、85、86、87、89、90、92、93、95、96、97、98、99、101、102、103、104、106、111、112、113、114、115、117、119、120、121、122、123、125、126、127、128、130、132、134、135、137、138、139、140、141、142、143、144、148、150、151、152、154、155、157、158、159、164、165、166、167、170、172、173、174、175、177、178、179、180、181、182、183、184、185、186、188、189、190、191、192、193、194、196、199、200、201、202、204、205、206、207、208、209、210、211、212、213、214、215、217、218、221、225、228、229、233、234、235、238、241、242、243、246、263、265、267、268、270、271、272、273、274、276、278、280、282、283、284、285、286、287、288、289、292、293、294、296、297、298、299、300、302、303、305、306、307、308、309、310、311、312、314、316、318、321、323、324、325、326、331、332、333、334、335、336、339、340、341、342、343、345、346、347、348、349、351、352、355、356、357、358、359、360、361、362、363、365、367、368、369、371、372、373、374、375、377、379、380、381、382、383、390、392、393、394、395、396、397、398、400、401、402、403、405、406、408、409、410、411、412、413、414、415、416、417、420、421、422、423、424、426、427、428、429、430、431、433、435、436、437、438、440、441、442、443、444、445、446、449、452、453、454、456、457、458、459、461、463、464、465、466、467、468、469、470、472、474、475、476、477、478、480、482、483、484、485、486、487、488、489、490、491、492、494、497、499、501、503、504、505、506、511、512、517、518、519、520、521、522、523、524、525、526、527、528、530、532、533、534、535、536、537及び538 Test Example 2: Bactericidal effect test against cucumber downy mildew ( Pseudoperonospora cubensis ) (preventive effect test)
Cucumbers were grown in vinyl pots with a diameter of 6 cm, and when they reached the 1.2 to 1.5 leaf stage, 10 ml of the chemical solution was sprayed with a spray gun. After the chemical solution had dried (on the day of treatment), a spore suspension of cucumber downy mildew (Pseudoperonospora cubensis) was spray inoculated and placed in an inoculation box at a temperature of 20° C. and a humidity of 95% or more for 24 hours. Thereafter, the plants were placed in a constant temperature room at 20° C., and the lesion area ratio was investigated 7 days after inoculation, and the control rate was calculated using the same formula as in Test Example 1 above. As a result, each composition (active ingredient concentration: 400 ppm) containing the following compounds showed a control rate of 90% or more against cucumber downy mildew.
Compound: No. 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 13, 14, 15, 17, 18, 19, 20, 21, 22, 23, 24, 26, 27, 28, 30, 31, 32, 33, 34, 39, 40, 41, 42, 46, 47, 48, 50, 51, 54, 55, 56, 58, 60, 62, 65, 66, 67, 68, 70, 71, 72, 73, 76, 77, 78, 79, 81, 83, 84, 85, 86, 87, 89, 90, 92, 93, 95, 96, 97, 98, 99, 101, 102, 103, 104, 106, 111, 112, 113, 114, 115, 117, 119, 120, 121, 122, 123, 125, 126, 127, 128, 130, 132, 134, 135, 137, 138, 139, 140, 141, 142, 143, 144, 148, 150, 151, 152, 154, 155, 157, 158, 159, 164, 165, 166, 167, 170, 172, 173, 174, 175, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186, 188, 189, 190, 191, 192, 193, 194, 196, 199, 200, 201, 202, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 217, 218, 221, 225, 228, 229, 233, 234, 235, 238, 241, 242, 243, 246, 263, 265, 267, 268, 270, 271, 272, 273, 274, 276, 278, 280, 282, 283, 284, 285, 286, 287, 288, 289, 292, 293, 294, 296, 297, 298, 299, 300, 302, 303, 305, 306, 307, 308, 309, 310, 311, 312, 314, 316, 318, 321, 323, 324, 325, 326, 331, 332, 333, 334, 335, 336, 339, 340, 341, 342, 343, 345, 346, 347, 348, 349, 351, 352, 355, 356, 357, 358, 359, 360, 361, 362, 363, 365, 367, 368, 369, 371, 372, 373, 374, 375, 377, 379, 380, 381, 382, 383, 390, 392, 393, 394, 395, 396, 397, 398, 400, 401, 402, 403, 405, 406, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 420, 421, 422, 423, 424, 426, 427, 428, 429, 430, 431, 433, 435, 436, 437, 438, 440, 441, 442, 443, 444, 445, 446, 449, 452, 453, 454, 456, 457, 458, 459, 461, 463, 464, 465, 466, 467, 468, 469, 470, 472, 474, 475, 476, 477, 478, 480, 482, 483, 484, 485, 486, 487, 488, 489, 490, 491, 492, 494, 497, 499, 501, 503, 504, 505, 506, 511, 512, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 530, 532, 533, 534, 535, 536, 537 and 538
試験例3:トマト疫病(Phytophthora infestans)に対する殺菌効果試験(治療効果試験)
直径6cmのビニールポットでトマトを栽培し、4.5~5.5葉期に達した時にトマト疫病菌(Phytophthora infestans)の胞子懸濁液を噴霧接種し、温度20℃、湿度95%以上の接種箱に4時間入れた。その後、薬液10mlをスプレーガンにて散布し、薬液が乾燥した後(処理当日)に、20℃の恒温室内に置き、接種3日後に病斑面積率を調査し、上記試験例1と同じ計算式により防除率を算出した。その結果、以下の化合物を含む各組成物(有効成分濃度は400ppm又は200ppm)がトマト疫病に対して90%以上の防除率を示した。なお、化合物No.35、160、177、及び179は有効成分濃度200ppmでトマト疫病に対して90%以上の防除率を示したものであり、それ以外の化合物は有効成分濃度400ppmでトマト疫病に対して90%以上の防除率を示したものである。
化合物:No.1、3、4、9、10、13、14、16、17、18、19、20、21、23、24、25、26、27、30、31、32、33、34、35、39、40、41、42、46、47、50、51、54、55、56、57、60、62、64、66、67、68、72、76、77、78、79、81、83、84、85、86、87、89、90、95、96、97、98、101、102、103、105、107、108、113、114、115、117、120、121、122、123、124、125、126、132、133、134、135、136、139、140、141、142、143、145、148、149、150、151、152、153、154、158、160、164、165、166、167、170、171、173、174、177、179、180、181、182、183、184、185、189、192、193、194、202、204、205、206、207、208、210、214、215、228、229、233、235、238、241、243、246、263、264、265、268、270、271、272、273、275、278、280、284、285、286、287、288、290、291、292、293、294、296、298、299、300、301、302、303、305、306、307、308、309、310、311、312、316、321、323、324、325、326、331、332、333、334、335、338、340、341、342、343、347、348、349、351、352、356、358、361、363、371、372、373、374、375、379、381、382、383、395、396、398、399、400、401、402、403、411、412、416、422、426、428、433、435、440、441、442、443、444、445、446、452、453、454、456、461、463、464、465、467、468、470、472、475、478、479、480、481、482、484、485、486、487、489、490、491、492、494、499、500、501、512、514、517、518、522、523、525、528、532、533、534、535、536、537及び538 Test Example 3: Bactericidal effect test against tomato late blight ( Phytophthora infestans ) (therapeutic effect test)
Tomatoes were grown in plastic pots with a diameter of 6 cm, and when they reached the 4.5-5.5 leaf stage, they were spray-inoculated with a spore suspension of Phytophthora infestans and grown at a temperature of 20°C and a humidity of 95% or higher. It was placed in the inoculation box for 4 hours. After that, 10ml of the chemical solution was sprayed with a spray gun, and after the chemical solution dried (on the day of treatment), it was placed in a constant temperature room at 20℃, and the lesion area ratio was investigated 3 days after inoculation, and the same calculation as in Test Example 1 was performed. The control rate was calculated using the formula. As a result, each composition containing the following compounds (active ingredient concentration: 400 ppm or 200 ppm) showed a control rate of 90% or more against tomato late blight. Compounds No. 35, 160, 177, and 179 showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 200 ppm, and the other compounds showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 400 ppm. This shows a control rate of 90% or more.
Compound: No. 1, 3, 4, 9, 10, 13, 14, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 30, 31, 32, 33, 34, 35, 39, 40, 41, 42, 46, 47, 50, 51, 54, 55, 56, 57, 60, 62, 64, 66, 67, 68, 72, 76, 77, 78, 79, 81, 83, 84, 85, 86, 87, 89, 90, 95, 96, 97, 98, 101, 102, 103, 105, 107, 108, 113, 114, 115, 117, 120, 121, 122, 123, 124, 125, 126, 132, 133, 134, 135, 136, 139, 140, 141, 142, 143, 145, 148, 149, 150, 151, 152, 153, 154, 158, 160, 164, 165, 166, 167, 170, 171, 173, 174, 177, 179, 180, 181, 182, 183, 184, 185, 189, 192, 193, 194, 202, 204, 205, 206, 207, 208, 210, 214, 215, 228, 229, 233, 235, 238, 241, 243, 246, 263, 264, 265, 268, 270, 271, 272, 273, 275, 278, 280, 284, 285, 286, 287, 288, 290, 291, 292, 293, 294, 296, 298, 299, 300, 301, 302, 303, 305, 306, 307, 308, 309, 310, 311, 312, 316, 321, 323, 324, 325, 326, 331, 332, 333, 334, 335, 338, 340, 341, 342, 343, 347, 348, 349, 351, 352, 356, 358, 361, 363, 371, 372, 373, 374, 375, 379, 381, 382, 383, 395, 396, 398, 399, 400, 401, 402, 403, 411, 412, 416, 422, 426, 428, 433, 435, 440, 441, 442, 443, 444, 445, 446, 452, 453, 454, 456, 461, 463, 464, 465, 467, 468, 470, 472, 475, 478, 479, 480, 481, 482, 484, 485, 486, 487, 489, 490, 491, 492, 494, 499, 500, 501, 512, 514, 517, 518, 522, 523, 525, 528, 532, 533, 534, 535, 536, 537 and 538
直径6cmのビニールポットでトマトを栽培し、4.5~5.5葉期に達した時にトマト疫病菌(Phytophthora infestans)の胞子懸濁液を噴霧接種し、温度20℃、湿度95%以上の接種箱に4時間入れた。その後、薬液10mlをスプレーガンにて散布し、薬液が乾燥した後(処理当日)に、20℃の恒温室内に置き、接種3日後に病斑面積率を調査し、上記試験例1と同じ計算式により防除率を算出した。その結果、以下の化合物を含む各組成物(有効成分濃度は400ppm又は200ppm)がトマト疫病に対して90%以上の防除率を示した。なお、化合物No.35、160、177、及び179は有効成分濃度200ppmでトマト疫病に対して90%以上の防除率を示したものであり、それ以外の化合物は有効成分濃度400ppmでトマト疫病に対して90%以上の防除率を示したものである。
化合物:No.1、3、4、9、10、13、14、16、17、18、19、20、21、23、24、25、26、27、30、31、32、33、34、35、39、40、41、42、46、47、50、51、54、55、56、57、60、62、64、66、67、68、72、76、77、78、79、81、83、84、85、86、87、89、90、95、96、97、98、101、102、103、105、107、108、113、114、115、117、120、121、122、123、124、125、126、132、133、134、135、136、139、140、141、142、143、145、148、149、150、151、152、153、154、158、160、164、165、166、167、170、171、173、174、177、179、180、181、182、183、184、185、189、192、193、194、202、204、205、206、207、208、210、214、215、228、229、233、235、238、241、243、246、263、264、265、268、270、271、272、273、275、278、280、284、285、286、287、288、290、291、292、293、294、296、298、299、300、301、302、303、305、306、307、308、309、310、311、312、316、321、323、324、325、326、331、332、333、334、335、338、340、341、342、343、347、348、349、351、352、356、358、361、363、371、372、373、374、375、379、381、382、383、395、396、398、399、400、401、402、403、411、412、416、422、426、428、433、435、440、441、442、443、444、445、446、452、453、454、456、461、463、464、465、467、468、470、472、475、478、479、480、481、482、484、485、486、487、489、490、491、492、494、499、500、501、512、514、517、518、522、523、525、528、532、533、534、535、536、537及び538 Test Example 3: Bactericidal effect test against tomato late blight ( Phytophthora infestans ) (therapeutic effect test)
Tomatoes were grown in plastic pots with a diameter of 6 cm, and when they reached the 4.5-5.5 leaf stage, they were spray-inoculated with a spore suspension of Phytophthora infestans and grown at a temperature of 20°C and a humidity of 95% or higher. It was placed in the inoculation box for 4 hours. After that, 10ml of the chemical solution was sprayed with a spray gun, and after the chemical solution dried (on the day of treatment), it was placed in a constant temperature room at 20℃, and the lesion area ratio was investigated 3 days after inoculation, and the same calculation as in Test Example 1 was performed. The control rate was calculated using the formula. As a result, each composition containing the following compounds (active ingredient concentration: 400 ppm or 200 ppm) showed a control rate of 90% or more against tomato late blight. Compounds No. 35, 160, 177, and 179 showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 200 ppm, and the other compounds showed a control rate of 90% or more against tomato late blight at an active ingredient concentration of 400 ppm. This shows a control rate of 90% or more.
Compound: No. 1, 3, 4, 9, 10, 13, 14, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 30, 31, 32, 33, 34, 35, 39, 40, 41, 42, 46, 47, 50, 51, 54, 55, 56, 57, 60, 62, 64, 66, 67, 68, 72, 76, 77, 78, 79, 81, 83, 84, 85, 86, 87, 89, 90, 95, 96, 97, 98, 101, 102, 103, 105, 107, 108, 113, 114, 115, 117, 120, 121, 122, 123, 124, 125, 126, 132, 133, 134, 135, 136, 139, 140, 141, 142, 143, 145, 148, 149, 150, 151, 152, 153, 154, 158, 160, 164, 165, 166, 167, 170, 171, 173, 174, 177, 179, 180, 181, 182, 183, 184, 185, 189, 192, 193, 194, 202, 204, 205, 206, 207, 208, 210, 214, 215, 228, 229, 233, 235, 238, 241, 243, 246, 263, 264, 265, 268, 270, 271, 272, 273, 275, 278, 280, 284, 285, 286, 287, 288, 290, 291, 292, 293, 294, 296, 298, 299, 300, 301, 302, 303, 305, 306, 307, 308, 309, 310, 311, 312, 316, 321, 323, 324, 325, 326, 331, 332, 333, 334, 335, 338, 340, 341, 342, 343, 347, 348, 349, 351, 352, 356, 358, 361, 363, 371, 372, 373, 374, 375, 379, 381, 382, 383, 395, 396, 398, 399, 400, 401, 402, 403, 411, 412, 416, 422, 426, 428, 433, 435, 440, 441, 442, 443, 444, 445, 446, 452, 453, 454, 456, 461, 463, 464, 465, 467, 468, 470, 472, 475, 478, 479, 480, 481, 482, 484, 485, 486, 487, 489, 490, 491, 492, 494, 499, 500, 501, 512, 514, 517, 518, 522, 523, 525, 528, 532, 533, 534, 535, 536, 537 and 538
次に、本組成物及び国際公開第2017/012965号に記載の化合物を含む組成物の植物病原菌に対する効果を以下の比較試験で示す。
Next, the effects of the present composition and the composition containing the compound described in International Publication No. 2017/012965 on plant pathogenic bacteria will be shown in the following comparative test.
比較試験
本組成物の有効成分として化合物No.78とNo.193を用い、国際公開第2017/012965号に記載の化合物を含む組成物として、下記に示される化合物D6-15を有効成分として用い、比較試験を行った。
各化合物を含む薬液の調製:各供試化合物を用いて、上記と同じ調製方法で各薬液を調製した。この薬液を、以下の比較試験例1にて利用した。
比較試験例1:トマト疫病に対する殺菌効果試験(予防効果試験)
トマト(直径6cmのビニールポットで栽培、4.5~5.5葉期)1ポットあたりに、薬液10mLをスプレーガンにて散布した。薬液が乾燥した後(処理当日または翌日)に、疫病菌(Phytophthora infestans)の胞子懸濁液を噴霧接種し、温度20℃、湿度95%以上の接種箱に16時間入れた。その後20℃の恒温室内に置き、接種3日後に病斑面積率を調査し、上記試験例1と同じ計算式により防除率を算出した。その結果を、第3表に示す。Aは100%の防除率、Bは90%以上100%未満の防除率、Cは70%以上90%未満の防除率、Dは30%以上70%未満の防除率、Eは0%以上30%未満の防除率をそれぞれ意味する。 Comparative Test Compounds No. 78 and No. 193 were used as the active ingredients of the present composition, and Compound D6-15 shown below was used as the active ingredient of a composition containing the compound described in International Publication No. 2017/012965. , conducted a comparative test.
Preparation of chemical solutions containing each compound: Using each test compound, each drug solution was prepared using the same preparation method as above. This chemical solution was used in Comparative Test Example 1 below.
Comparative test example 1: Bactericidal effect test against tomato late blight (preventive effect test)
10 mL of the chemical solution was sprayed onto each tomato pot (cultivated in a vinyl pot with a diameter of 6 cm, 4.5 to 5.5 leaf stage) using a spray gun. After the chemical solution dried (on the day of treatment or the next day), a spore suspension of Phytophthora infestans was spray inoculated and placed in an inoculation box at a temperature of 20° C. and a humidity of 95% or more for 16 hours. Thereafter, the plants were placed in a constant temperature room at 20° C., and the lesion area ratio was investigated 3 days after inoculation, and the control rate was calculated using the same formula as in Test Example 1 above. The results are shown in Table 3. A is 100% control rate, B is 90% or more and less than 100% control rate, C is 70% or more and less than 90% control rate, D is 30% or more and less than 70% control rate, E is 0% or more and 30 Each means a control rate of less than %.
本組成物の有効成分として化合物No.78とNo.193を用い、国際公開第2017/012965号に記載の化合物を含む組成物として、下記に示される化合物D6-15を有効成分として用い、比較試験を行った。
各化合物を含む薬液の調製:各供試化合物を用いて、上記と同じ調製方法で各薬液を調製した。この薬液を、以下の比較試験例1にて利用した。
比較試験例1:トマト疫病に対する殺菌効果試験(予防効果試験)
トマト(直径6cmのビニールポットで栽培、4.5~5.5葉期)1ポットあたりに、薬液10mLをスプレーガンにて散布した。薬液が乾燥した後(処理当日または翌日)に、疫病菌(Phytophthora infestans)の胞子懸濁液を噴霧接種し、温度20℃、湿度95%以上の接種箱に16時間入れた。その後20℃の恒温室内に置き、接種3日後に病斑面積率を調査し、上記試験例1と同じ計算式により防除率を算出した。その結果を、第3表に示す。Aは100%の防除率、Bは90%以上100%未満の防除率、Cは70%以上90%未満の防除率、Dは30%以上70%未満の防除率、Eは0%以上30%未満の防除率をそれぞれ意味する。 Comparative Test Compounds No. 78 and No. 193 were used as the active ingredients of the present composition, and Compound D6-15 shown below was used as the active ingredient of a composition containing the compound described in International Publication No. 2017/012965. , conducted a comparative test.
Preparation of chemical solutions containing each compound: Using each test compound, each drug solution was prepared using the same preparation method as above. This chemical solution was used in Comparative Test Example 1 below.
Comparative test example 1: Bactericidal effect test against tomato late blight (preventive effect test)
10 mL of the chemical solution was sprayed onto each tomato pot (cultivated in a vinyl pot with a diameter of 6 cm, 4.5 to 5.5 leaf stage) using a spray gun. After the chemical solution dried (on the day of treatment or the next day), a spore suspension of Phytophthora infestans was spray inoculated and placed in an inoculation box at a temperature of 20° C. and a humidity of 95% or more for 16 hours. Thereafter, the plants were placed in a constant temperature room at 20° C., and the lesion area ratio was investigated 3 days after inoculation, and the control rate was calculated using the same formula as in Test Example 1 above. The results are shown in Table 3. A is 100% control rate, B is 90% or more and less than 100% control rate, C is 70% or more and less than 90% control rate, D is 30% or more and less than 70% control rate, E is 0% or more and 30 Each means a control rate of less than %.
次に、本組成物の製剤例を記載するが、配合割合、剤型などは記載例に限定されるものではない。
製剤例1
(1)式(I)の化合物 20重量部
(2)クレー 72重量部
(3)リグニンスルホン酸ソーダ 8重量部
以上のものを均一に混合して水和剤とする。
製剤例2
(1)式(I)の化合物 5重量部
(2)タルク 95重量部
以上のものを均一に混合して粉剤とする。
製剤例3
(1)式(I)の化合物 20重量部
(2)N,N’-ジメチルアセトアミド 20重量部
(3)ポリオキシエチレンアルキルフェニルエーテル 10重量部
(4)キシレン 50重量部
以上のものを均一に混合、溶解して乳剤とする。 Next, formulation examples of the present composition will be described, but the blending ratio, dosage form, etc. are not limited to the described examples.
Formulation example 1
(1) 20 parts by weight of the compound of formula (I), (2) 72 parts by weight of clay, and (3) 8 parts by weight or more of sodium ligninsulfonate are uniformly mixed to prepare a wettable powder.
Formulation example 2
(1) 5 parts by weight of the compound of formula (I) (2) 95 parts by weight or more of talc are uniformly mixed to form a powder.
Formulation example 3
(1) Compound of formula (I) 20 parts by weight (2) N,N'-dimethylacetamide 20 parts by weight (3) Polyoxyethylene alkylphenyl ether 10 parts by weight (4) Xylene 50 parts by weight or more uniformly Mix and dissolve to form an emulsion.
製剤例1
(1)式(I)の化合物 20重量部
(2)クレー 72重量部
(3)リグニンスルホン酸ソーダ 8重量部
以上のものを均一に混合して水和剤とする。
製剤例2
(1)式(I)の化合物 5重量部
(2)タルク 95重量部
以上のものを均一に混合して粉剤とする。
製剤例3
(1)式(I)の化合物 20重量部
(2)N,N’-ジメチルアセトアミド 20重量部
(3)ポリオキシエチレンアルキルフェニルエーテル 10重量部
(4)キシレン 50重量部
以上のものを均一に混合、溶解して乳剤とする。 Next, formulation examples of the present composition will be described, but the blending ratio, dosage form, etc. are not limited to the described examples.
Formulation example 1
(1) 20 parts by weight of the compound of formula (I), (2) 72 parts by weight of clay, and (3) 8 parts by weight or more of sodium ligninsulfonate are uniformly mixed to prepare a wettable powder.
Formulation example 2
(1) 5 parts by weight of the compound of formula (I) (2) 95 parts by weight or more of talc are uniformly mixed to form a powder.
Formulation example 3
(1) Compound of formula (I) 20 parts by weight (2) N,N'-dimethylacetamide 20 parts by weight (3) Polyoxyethylene alkylphenyl ether 10 parts by weight (4) Xylene 50 parts by weight or more uniformly Mix and dissolve to form an emulsion.
製剤例4
(1)クレー 68重量部
(2)リグニンスルホン酸ソーダ 2重量部
(3)ポリオキシエチレンアルキルアリールサルフェート 5重量部
(4)微粉シリカ 25重量部
以上の各成分の混合物と、式(I)の化合物とを4:1の重量割合で混合し、水和剤とする。
製剤例5
(1)式(I)の化合物 50重量部
(2)ポリオキシエチレンアルキルフェニルエーテルリン酸トリエタノールアミン塩
2重量部
(3)シリコーン 0.2重量部
(4)水 47.8重量部
以上のものを均一に混合、粉砕した原液に更に
(5)ポリカルボン酸ナトリウム 5重量部
(6)無水硫酸ナトリウム 42.8重量部
を加え均一に混合、造粒、乾燥して顆粒水和剤とする。
製剤例6
(1)式(I)の化合物 5重量部
(2)ポリオキシエチレンオクチルフェニルエーテル 1重量部
(3)ポリオキシエチレンの燐酸エステル 0.1重量部
(4)粒状炭酸カルシウム 93.9重量部
(1)~(3)を予め均一に混合し、適量のアセトンで希釈した後、(4)に吹付け、アセトンを除去して粒剤とする。 Formulation example 4
(1) Clay 68 parts by weight (2) Sodium ligninsulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) Finely divided silica A mixture of 25 parts by weight or more of each component and the formula (I) compound at a weight ratio of 4:1 to form a wettable powder.
Formulation example 5
(1) Compound of formula (I) 50 parts by weight (2) Polyoxyethylene alkylphenyl ether phosphate triethanolamine salt 2 parts by weight (3) Silicone 0.2 part by weight (4) Water 47.8 parts by weight or more Further, (5) 5 parts by weight of sodium polycarboxylate and (6) 42.8 parts by weight of anhydrous sodium sulfate are added to the undiluted solution after uniformly mixing and pulverizing the ingredients, and the mixture is uniformly mixed, granulated, and dried to form a granule wettable powder. .
Formulation example 6
(1) Compound of formula (I) 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Phosphate of polyoxyethylene 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight ( 1) to (3) are mixed uniformly in advance, diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove the acetone to form granules.
(1)クレー 68重量部
(2)リグニンスルホン酸ソーダ 2重量部
(3)ポリオキシエチレンアルキルアリールサルフェート 5重量部
(4)微粉シリカ 25重量部
以上の各成分の混合物と、式(I)の化合物とを4:1の重量割合で混合し、水和剤とする。
製剤例5
(1)式(I)の化合物 50重量部
(2)ポリオキシエチレンアルキルフェニルエーテルリン酸トリエタノールアミン塩
2重量部
(3)シリコーン 0.2重量部
(4)水 47.8重量部
以上のものを均一に混合、粉砕した原液に更に
(5)ポリカルボン酸ナトリウム 5重量部
(6)無水硫酸ナトリウム 42.8重量部
を加え均一に混合、造粒、乾燥して顆粒水和剤とする。
製剤例6
(1)式(I)の化合物 5重量部
(2)ポリオキシエチレンオクチルフェニルエーテル 1重量部
(3)ポリオキシエチレンの燐酸エステル 0.1重量部
(4)粒状炭酸カルシウム 93.9重量部
(1)~(3)を予め均一に混合し、適量のアセトンで希釈した後、(4)に吹付け、アセトンを除去して粒剤とする。 Formulation example 4
(1) Clay 68 parts by weight (2) Sodium ligninsulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) Finely divided silica A mixture of 25 parts by weight or more of each component and the formula (I) compound at a weight ratio of 4:1 to form a wettable powder.
Formulation example 5
(1) Compound of formula (I) 50 parts by weight (2) Polyoxyethylene alkylphenyl ether phosphate triethanolamine salt 2 parts by weight (3) Silicone 0.2 part by weight (4) Water 47.8 parts by weight or more Further, (5) 5 parts by weight of sodium polycarboxylate and (6) 42.8 parts by weight of anhydrous sodium sulfate are added to the undiluted solution after uniformly mixing and pulverizing the ingredients, and the mixture is uniformly mixed, granulated, and dried to form a granule wettable powder. .
Formulation example 6
(1) Compound of formula (I) 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Phosphate of polyoxyethylene 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight ( 1) to (3) are mixed uniformly in advance, diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove the acetone to form granules.
製剤例7
(1)式(I)の化合物 2.5重量部
(2)N-メチル-2-ピロリドン 2.5重量部
(3)大豆油 95.0重量部
以上のものを均一に混合、溶解して微量散布剤(ultra low volume formulation)とする。
製剤例8
(1)式(I)の化合物 20重量部
(2)ポリオキシエチレンアルキルフェニルエーテルリン酸トリエタノールアミン塩
2重量部
(3)シリコーン 0.2重量部
(4)ザンサンガム 0.1重量部
(5)エチレングリコール 5重量部
(6)水 72.7重量部
以上のものを均一に混合、粉砕して水性懸濁剤とする。 Formulation example 7
(1) Compound of formula (I) 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved. Ultra low volume formulation.
Formulation example 8
(1) Compound of formula (I) 20 parts by weight (2) Polyoxyethylene alkylphenyl ether phosphate triethanolamine salt 2 parts by weight (3) Silicone 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5 ) Ethylene glycol 5 parts by weight (6) Water 72.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.
(1)式(I)の化合物 2.5重量部
(2)N-メチル-2-ピロリドン 2.5重量部
(3)大豆油 95.0重量部
以上のものを均一に混合、溶解して微量散布剤(ultra low volume formulation)とする。
製剤例8
(1)式(I)の化合物 20重量部
(2)ポリオキシエチレンアルキルフェニルエーテルリン酸トリエタノールアミン塩
2重量部
(3)シリコーン 0.2重量部
(4)ザンサンガム 0.1重量部
(5)エチレングリコール 5重量部
(6)水 72.7重量部
以上のものを均一に混合、粉砕して水性懸濁剤とする。 Formulation example 7
(1) Compound of formula (I) 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved. Ultra low volume formulation.
Formulation example 8
(1) Compound of formula (I) 20 parts by weight (2) Polyoxyethylene alkylphenyl ether phosphate triethanolamine salt 2 parts by weight (3) Silicone 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5 ) Ethylene glycol 5 parts by weight (6) Water 72.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.
なお、2022年3月18日に出願された日本特許出願2022-043827号の明細書、特許請求の範囲および要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。
The entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2022-043827 filed on March 18, 2022 are cited here and incorporated as disclosure of the specification of the present invention. It is.
Claims (9)
- 式(I):
R2はH又は(C1-C3)-アルキルであり、
R3は(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、(C3-C4)-シクロアルキル、(C2-C4)-ハロアルケニル、少なくとも1個のZで置換された(C1-C3)-アルキル、又はHであり、
R2とR3が一緒になって、R2とR3に結合した窒素原子と3~5員環を形成してもよく、
Zはシアノ、ハロゲン、(C1-C3)-アルコキシ、(C3)-シクロアルキル、(C1-C3)-アルキルチオ、-C(=O)RZ、ヒドロキシ、又はトリ(C1-C4)-アルキルシリルオキシであり、
RZは(C1-C4)-アルキル、(C3-C6)-シクロアルキルオキシ、(C1-C4)-アルコキシ、フェノキシ、ベンジルオキシ、又はヒドロキシであり、
R4はハロゲン、(C1-C3)-アルキル、(C1-C3)-ハロアルキル、ニトロ、シアノ、(C1-C3)-アルキルチオ、(C1-C3)-ハロアルキルチオ、(C2-C3)-アルケニル、(C2-C3)-ハロアルケニル、又は(C1-C3)-アルコキシであり、
nは1から5の整数である]で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩を有効成分として含有する殺菌組成物。 Formula (I):
R 2 is H or (C 1 -C 3 )-alkyl;
R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 3 )-alkyl substituted with at least one Z, or H;
R 2 and R 3 may be taken together to form a 3- to 5-membered ring with the nitrogen atom bonded to R 2 and R 3 ,
Z is cyano, halogen, (C 1 -C 3 )-alkoxy, (C 3 )-cycloalkyl, (C 1 -C 3 )-alkylthio, -C(=O)R Z , hydroxy, or tri(C 1 -C 4 )-alkylsilyloxy,
R Z is (C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyloxy, (C 1 -C 4 )-alkoxy, phenoxy, benzyloxy, or hydroxy;
R 4 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, nitro, cyano, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-haloalkylthio, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, or (C 1 -C 3 )-alkoxy,
n is an integer from 1 to 5] A sterilizing composition containing a thiazolecarboxylic acid hydrazide compound or a salt thereof as an active ingredient. - 式(I):
R2はH又は(C1-C3)-アルキルであり、
R3は(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、(C3-C4)-シクロアルキル、(C2-C4)-ハロアルケニル、少なくとも1個のZで置換された(C1-C3)-アルキル、又はHであり、
R2とR3が一緒になって、R2とR3に結合した窒素原子と3~5員環を形成してもよく、
Zはシアノ、ハロゲン、(C1-C3)-アルコキシ、(C3)-シクロアルキル、(C1-C3)-アルキルチオ、-C(=O)RZ、 ヒドロキシ、又はトリ(C1-C4)-アルキルシリルオキシであり、
RZは(C1-C4)-アルキル、(C3-C6)-シクロアルキルオキシ、(C1-C4)-アルコキシ、フェノキシ、ベンジルオキシ、又はヒドロキシであり、
R4はハロゲン、(C1-C3)-アルキル、(C1-C3)-ハロアルキル、ニトロ、シアノ、(C1-C3)-アルキルチオ、(C1-C3)-ハロアルキルチオ、(C2-C3)-アルケニル、(C2-C3)-ハロアルケニル、又は(C1-C3)-アルコキシであり、
nは1から5の整数である]で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩の有効量を、植物体、植物病原菌又は土壌に施用する工程を含む有害な植物病害を防除する方法。 Formula (I):
R 2 is H or (C 1 -C 3 )-alkyl;
R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 3 )-alkyl substituted with at least one Z, or H;
R 2 and R 3 may be taken together to form a 3- to 5-membered ring with the nitrogen atom bonded to R 2 and R 3 ,
Z is cyano, halogen, (C 1 -C 3 )-alkoxy, (C 3 )-cycloalkyl, (C 1 -C 3 )-alkylthio, -C(=O)R Z , hydroxy, or tri(C 1 ) -C 4 )-alkylsilyloxy,
R Z is (C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyloxy, (C 1 -C 4 )-alkoxy, phenoxy, benzyloxy, or hydroxy;
R 4 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, nitro, cyano, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-haloalkylthio, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, or (C 1 -C 3 )-alkoxy,
A method for controlling harmful plant diseases, which comprises applying an effective amount of a thiazolecarboxylic acid hydrazide compound or a salt thereof represented by [n is an integer from 1 to 5] to plants, plant pathogens, or soil. - 式(I):
R2はH又は(C1-C3)-アルキルであり、
R3は(C1-C3)-アルキル、(C2-C5)-アルキニル、(C2-C4)-アルケニル、(C3-C4)-シクロアルキル、(C2-C4)-ハロアルケニル、少なくとも1個のZで置換された(C1-C3)-アルキル、又はHであり、
R2とR3が一緒になって、R2とR3に結合した窒素原子と3~5員環を形成してもよく、
Zはシアノ、ハロゲン、(C1-C3)-アルコキシ、(C3)-シクロアルキル、(C1-C3)-アルキルチオ、-C(=O)RZ、ヒドロキシ、又はトリ(C1-C4)-アルキルシリルオキシであり、
RZは(C1-C4)-アルキル、(C3-C6)-シクロアルキルオキシ、(C1-C4)-アルコキシ、フェノキシ、ベンジルオキシ、又はヒドロキシであり、
R4はハロゲン、(C1-C3)-アルキル、(C1-C3)-ハロアルキル、ニトロ、シアノ、(C1-C3)-アルキルチオ、(C1-C3)-ハロアルキルチオ、(C2-C3)-アルケニル、(C2-C3)-ハロアルケニル、又は(C1-C3)-アルコキシであり、
nは1から5の整数である]で表されるチアゾールカルボン酸ヒドラジド化合物又はその塩。 Formula (I):
R 2 is H or (C 1 -C 3 )-alkyl;
R 3 is (C 1 -C 3 )-alkyl, (C 2 -C 5 )-alkynyl, (C 2 -C 4 )-alkenyl, (C 3 -C 4 )-cycloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 3 )-alkyl substituted with at least one Z, or H;
R 2 and R 3 may be taken together to form a 3- to 5-membered ring with the nitrogen atom bonded to R 2 and R 3 ,
Z is cyano, halogen, (C 1 -C 3 )-alkoxy, (C 3 )-cycloalkyl, (C 1 -C 3 )-alkylthio, -C(=O)R Z , hydroxy, or tri(C 1 -C 4 )-alkylsilyloxy,
R Z is (C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyloxy, (C 1 -C 4 )-alkoxy, phenoxy, benzyloxy, or hydroxy;
R 4 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, nitro, cyano, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-haloalkylthio, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, or (C 1 -C 3 )-alkoxy,
n is an integer from 1 to 5] A thiazolecarboxylic acid hydrazide compound or a salt thereof. - 式(IA):
R3Aはメチル、エチル、ノルマルプロピル、プロパルギル、アリル、又はシクロプロピルであり、
R4Aはハロゲン、(C1-C2)-アルキル、(C1)-ハロアルキル、ニトロ、シアノ、(C1)-アルキルチオ、又は(C1)-ハロアルキルチオであり、
nは1から5の整数である]で表される、請求項3に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。 Formula (IA):
R 3A is methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl;
R 4A is halogen, (C 1 -C 2 )-alkyl, (C 1 )-haloalkyl, nitro, cyano, (C 1 )-alkylthio, or (C 1 )-haloalkylthio;
The thiazolecarboxylic acid hydrazide compound or its salt according to claim 3, wherein n is an integer from 1 to 5. - R3Aがメチル、エチル、又はプロパルギルである、請求項4に記載の化合物又はその塩。 5. The compound or salt thereof according to claim 4, wherein R 3A is methyl, ethyl, or propargyl.
- 式(IB):
R3Bはメチル、エチル、ノルマルプロピル、プロパルギル、アリル、又はシクロプロピルであり、
R4Bはハロゲン、(C1-C2)-アルキル、(C1)-ハロアルキル、ニトロ、シアノ、(C1)-アルキルチオ、又は(C1)-ハロアルキルチオであり、
nは1から5の整数である]で表される、請求項3に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩。 Formula (IB):
R 3B is methyl, ethyl, normal propyl, propargyl, allyl, or cyclopropyl;
R 4B is halogen, (C 1 -C 2 )-alkyl, (C 1 )-haloalkyl, nitro, cyano, (C 1 )-alkylthio, or (C 1 )-haloalkylthio;
The thiazolecarboxylic acid hydrazide compound or its salt according to claim 3, wherein n is an integer from 1 to 5. - R3Bがメチル、エチル、又はプロパルギルである、請求項6に記載の化合物又はその塩。 7. The compound or salt thereof according to claim 6, wherein R 3B is methyl, ethyl, or propargyl.
- 前記請求項4又は6に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩を有効成分として含有する殺菌組成物。 A sterilizing composition containing the thiazolecarboxylic acid hydrazide compound or its salt according to claim 4 or 6 as an active ingredient.
- 前記請求項4又は6に記載のチアゾールカルボン酸ヒドラジド化合物又はその塩の有効量を、植物体、植物病原菌又は土壌に施用する工程を含む有害な植物病害を防除する方法。 A method for controlling harmful plant diseases, comprising the step of applying an effective amount of the thiazolecarboxylic acid hydrazide compound or its salt according to claim 4 or 6 to plants, plant pathogens, or soil.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2022-043827 | 2022-03-18 | ||
JP2022043827 | 2022-03-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2023176458A1 true WO2023176458A1 (en) | 2023-09-21 |
Family
ID=88023575
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2023/007646 WO2023176458A1 (en) | 2022-03-18 | 2023-03-01 | Disinfecting composition containing thiazole carboxylic acid hydrazide compound |
Country Status (2)
Country | Link |
---|---|
TW (1) | TW202400567A (en) |
WO (1) | WO2023176458A1 (en) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0931069A (en) * | 1995-07-24 | 1997-02-04 | Nissan Chem Ind Ltd | Thiazolecarboxylic acid derivative and plant disease injury controller |
WO2010134634A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
WO2010134628A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
JP2013536228A (en) * | 2010-08-20 | 2013-09-19 | ダウ アグロサイエンシィズ エルエルシー | Synergistic fungicidal and algicidal composition comprising 2-hydroxyphenyl aldehyde and 2-hydroxyphenyl ketone heterocycloylhydrazone and copper |
JP2018526337A (en) * | 2015-07-17 | 2018-09-13 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | Substituted heteroaryl carboxylic acid hydrazides or salts thereof, and their use to enhance stress tolerance in plants |
CN111875559A (en) * | 2020-08-17 | 2020-11-03 | 南京农业大学 | Thiazole hydrazide derivatives and application thereof as agricultural bactericide |
-
2023
- 2023-03-01 WO PCT/JP2023/007646 patent/WO2023176458A1/en unknown
- 2023-03-13 TW TW112109084A patent/TW202400567A/en unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0931069A (en) * | 1995-07-24 | 1997-02-04 | Nissan Chem Ind Ltd | Thiazolecarboxylic acid derivative and plant disease injury controller |
WO2010134634A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
WO2010134628A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
JP2013536228A (en) * | 2010-08-20 | 2013-09-19 | ダウ アグロサイエンシィズ エルエルシー | Synergistic fungicidal and algicidal composition comprising 2-hydroxyphenyl aldehyde and 2-hydroxyphenyl ketone heterocycloylhydrazone and copper |
JP2018526337A (en) * | 2015-07-17 | 2018-09-13 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | Substituted heteroaryl carboxylic acid hydrazides or salts thereof, and their use to enhance stress tolerance in plants |
CN111875559A (en) * | 2020-08-17 | 2020-11-03 | 南京农业大学 | Thiazole hydrazide derivatives and application thereof as agricultural bactericide |
Also Published As
Publication number | Publication date |
---|---|
TW202400567A (en) | 2024-01-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2132987B1 (en) | Nematicidal agent composition and method of using the same | |
TWI823961B (en) | Thienyloxazolones and analogues | |
JP5940369B2 (en) | How to control plant diseases | |
ES2923515T3 (en) | Anthranilic acid ester compound, agricultural and horticultural microbicide comprising the compound, and method of using the microbicide | |
JP2009023994A (en) | Agricultural and horticultural bactericide composition and usage thereof | |
CN111566097B (en) | Oxadiazole compounds or salts thereof, agrohorticultural fungicides containing the same, and methods of use thereof | |
WO2019124537A1 (en) | N-methoxyamide compound or salt thereof, and agricultural and horticultural fungicide containing same | |
WO2019124538A1 (en) | N-methoxyamide compound or salt thereof, and agricultural and horticultural fungicide containing same | |
CN115515426A (en) | Active compound combinations and fungicide compositions comprising them | |
US11324219B2 (en) | Amide compound or salt thereof, agricultural and horticultural microbicide comprising the compound and the salt, and method for using the agricultural and horticultural microbicide | |
TW201802072A (en) | Novel compound and agricultural/horticultural chemical using same as active ingredient | |
CN114585620A (en) | Oxadiazole compound or salt thereof, agricultural/horticultural fungicide containing the same, and method for using the same | |
EP4285723A2 (en) | Substituted thiophene carboxamides, thiophene carboxylic acids and derivatives thereof | |
WO2013111864A1 (en) | Pest control agent | |
JP2019142776A (en) | Pest control agent containing n-(4-pyridyl) benzamide compound or salt thereof as active ingredient | |
CN114616231A (en) | Oxadiazoline compound or salt thereof, agricultural or horticultural fungicide containing the same, and method for using the same | |
WO2023176458A1 (en) | Disinfecting composition containing thiazole carboxylic acid hydrazide compound | |
JP2014015449A (en) | Bactericide composition, and method for controlling plant disease | |
JP2023137573A (en) | Bactericidal composition including thiazole carboxylic acid hydrazide compound | |
JPWO2013141362A1 (en) | Thiazolecarboxamide derivatives and methods of use thereof | |
JP2016179944A (en) | Difluoromethylene compound | |
RU2797513C2 (en) | Substituted thiophenecarboxamides and analogues as antibacterial agents | |
JP2019026575A (en) | Novel compound and bactericide for agricultural and horticultural use containing the same as active ingredient | |
JP2017008029A (en) | Pest control agent comprising n-(4-pyridyl)picoline amide compound or salt thereof as active ingredient | |
WO2024117205A1 (en) | Bicyclic pyridine derivative and salt thereof, and harmful organism control agent characterized by containing said derivative or salt thereof as active ingredient |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 23770416 Country of ref document: EP Kind code of ref document: A1 |