CN115594641B - 一类含苄基1,2,3-三唑结构的化合物及其作为杀菌剂的应用 - Google Patents
一类含苄基1,2,3-三唑结构的化合物及其作为杀菌剂的应用 Download PDFInfo
- Publication number
- CN115594641B CN115594641B CN202211587729.4A CN202211587729A CN115594641B CN 115594641 B CN115594641 B CN 115594641B CN 202211587729 A CN202211587729 A CN 202211587729A CN 115594641 B CN115594641 B CN 115594641B
- Authority
- CN
- China
- Prior art keywords
- compound
- compounds
- rice blast
- anthracnose
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- -1 1,2, 3-triazole structure compound Chemical class 0.000 title description 42
- 230000000844 anti-bacterial effect Effects 0.000 title description 16
- 239000003899 bactericide agent Substances 0.000 title description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 201000010099 disease Diseases 0.000 claims abstract description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 48
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 240000007594 Oryza sativa Species 0.000 claims abstract description 35
- 235000007164 Oryza sativa Nutrition 0.000 claims abstract description 35
- 235000009566 rice Nutrition 0.000 claims abstract description 35
- 241000196324 Embryophyta Species 0.000 claims abstract description 31
- 241000221785 Erysiphales Species 0.000 claims abstract description 12
- 241000233679 Peronosporaceae Species 0.000 claims abstract description 11
- 241000233614 Phytophthora Species 0.000 claims abstract description 7
- 239000000575 pesticide Substances 0.000 claims abstract description 3
- 239000004480 active ingredient Substances 0.000 claims description 13
- 235000021307 Triticum Nutrition 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 230000000361 pesticidal effect Effects 0.000 claims description 9
- 235000002566 Capsicum Nutrition 0.000 claims description 7
- 239000006002 Pepper Substances 0.000 claims description 7
- 235000016761 Piper aduncum Nutrition 0.000 claims description 7
- 235000017804 Piper guineense Nutrition 0.000 claims description 7
- 235000008184 Piper nigrum Nutrition 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 239000003223 protective agent Substances 0.000 claims description 6
- 241000233622 Phytophthora infestans Species 0.000 claims description 5
- 240000008042 Zea mays Species 0.000 claims description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 4
- 235000005822 corn Nutrition 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 3
- 235000016623 Fragaria vesca Nutrition 0.000 claims description 3
- 240000009088 Fragaria x ananassa Species 0.000 claims description 3
- 235000011363 Fragaria x ananassa Nutrition 0.000 claims description 3
- 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 claims description 3
- 241000233616 Phytophthora capsici Species 0.000 claims description 2
- 244000203593 Piper nigrum Species 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 244000241257 Cucumis melo Species 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 20
- 230000035784 germination Effects 0.000 abstract description 12
- 239000003814 drug Substances 0.000 abstract description 9
- 230000012010 growth Effects 0.000 abstract description 8
- 230000002401 inhibitory effect Effects 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 8
- 229940079593 drug Drugs 0.000 abstract description 4
- 230000006378 damage Effects 0.000 abstract description 3
- 244000052616 bacterial pathogen Species 0.000 abstract description 2
- 125000001399 1,2,3-triazolyl group Chemical class N1N=NC(=C1)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 150000003839 salts Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 210000002199 attachment cell Anatomy 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- 241000233654 Oomycetes Species 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 238000011081 inoculation Methods 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 241000233866 Fungi Species 0.000 description 12
- 241001330975 Magnaporthe oryzae Species 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 241000209140 Triticum Species 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000012453 solvate Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 244000053095 fungal pathogen Species 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 150000000177 1,2,3-triazoles Chemical class 0.000 description 5
- KUFNEMCYFOJAGR-UHFFFAOYSA-N 4-benzyl-2h-triazole Chemical group C=1C=CC=CC=1CC1=CNN=N1 KUFNEMCYFOJAGR-UHFFFAOYSA-N 0.000 description 5
- 239000005747 Chlorothalonil Substances 0.000 description 5
- 239000005776 Fenhexamid Substances 0.000 description 5
- 240000003889 Piper guineense Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000005842 Thiophanate-methyl Substances 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 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 5
- 230000000155 isotopic effect Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 5
- 239000005760 Difenoconazole Substances 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 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 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000005286 illumination Methods 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000001717 pathogenic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 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 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005730 Azoxystrobin Substances 0.000 description 3
- 239000005740 Boscalid Substances 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- 239000005757 Cyproconazole Substances 0.000 description 3
- 239000005758 Cyprodinil Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005788 Fluxapyroxad Substances 0.000 description 3
- 241001344131 Magnaporthe grisea Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000005811 Myclobutanil Substances 0.000 description 3
- 239000005820 Prochloraz Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 229940118790 boscalid Drugs 0.000 description 3
- 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 3
- 239000006013 carbendazim Substances 0.000 description 3
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 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 3
- 239000008187 granular material Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 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 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NCVWJDISIZHFQS-CQSZACIVSA-N (-)-antofine Chemical compound C12=CC(OC)=C(OC)C=C2C2=CC(OC)=CC=C2C2=C1C[C@H]1CCCN1C2 NCVWJDISIZHFQS-CQSZACIVSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 238000005160 1H NMR spectroscopy Methods 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
- 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 2
- 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 2
- 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 2
- 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 2
- 241000894006 Bacteria Species 0.000 description 2
- 239000005734 Benalaxyl Substances 0.000 description 2
- 229940123208 Biguanide Drugs 0.000 description 2
- 239000005738 Bixafen Substances 0.000 description 2
- 239000005739 Bordeaux mixture Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000005745 Captan Substances 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000219112 Cucumis Species 0.000 description 2
- 239000005756 Cymoxanil Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005775 Fenbuconazole Substances 0.000 description 2
- 239000005777 Fenpropidin Substances 0.000 description 2
- 239000005783 Fluopyram Substances 0.000 description 2
- 239000005784 Fluoxastrobin Substances 0.000 description 2
- 239000005785 Fluquinconazole Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005794 Hymexazol Substances 0.000 description 2
- 241000700189 Hystrix <Rodentia> Species 0.000 description 2
- 238000004566 IR spectroscopy Methods 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
- 239000005795 Imazalil Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005799 Isopyrazam Substances 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 239000005807 Metalaxyl Substances 0.000 description 2
- 239000005868 Metconazole Substances 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- 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 2
- 239000005815 Penflufen Substances 0.000 description 2
- 239000005816 Penthiopyrad Substances 0.000 description 2
- 239000005869 Pyraclostrobin Substances 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 239000005839 Tebuconazole Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000011230 binding agent Substances 0.000 description 2
- 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 2
- 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 2
- 229940117949 captan Drugs 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 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 2
- 235000021186 dishes Nutrition 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229960002125 enilconazole Drugs 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 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 2
- 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 2
- 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 2
- 230000002538 fungal effect Effects 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 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 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- 244000005700 microbiome Species 0.000 description 2
- 239000010413 mother solution Substances 0.000 description 2
- 230000001338 necrotic effect Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000004382 potting Methods 0.000 description 2
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 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 2
- 230000002829 reductive effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 235000010378 sodium ascorbate Nutrition 0.000 description 2
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 2
- 229960005055 sodium ascorbate Drugs 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- BXOCHUWSGYYSFW-HVWOQQCMSA-N spilanthol Chemical compound C\C=C\C=C/CC\C=C\C(=O)NCC(C)C BXOCHUWSGYYSFW-HVWOQQCMSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000008223 sterile water Substances 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
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 239000004308 thiabendazole Substances 0.000 description 2
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 2
- 235000010296 thiabendazole Nutrition 0.000 description 2
- 229960004546 thiabendazole Drugs 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 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 2
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 2
- 238000002255 vaccination Methods 0.000 description 2
- 239000012224 working solution Substances 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-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
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- JUSWZYFYLXTMLJ-JTQLQIEISA-N (2s)-1-(benzenesulfonyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1S(=O)(=O)C1=CC=CC=C1 JUSWZYFYLXTMLJ-JTQLQIEISA-N 0.000 description 1
- RQYKQWFHJOBBAO-JTQLQIEISA-N (2s)-1-benzoylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1 RQYKQWFHJOBBAO-JTQLQIEISA-N 0.000 description 1
- AMNAZJFEONUVTD-KEWDHRJRSA-N (2s,3s,4s,5r,6r)-6-(4-amino-2-oxopyrimidin-1-yl)-4,5-dihydroxy-3-[[(2s)-3-hydroxy-2-[[2-(methylamino)acetyl]amino]propanoyl]amino]oxane-2-carboxamide Chemical compound O1[C@H](C(N)=O)[C@@H](NC(=O)[C@H](CO)NC(=O)CNC)[C@H](O)[C@@H](O)[C@@H]1N1C(=O)N=C(N)C=C1 AMNAZJFEONUVTD-KEWDHRJRSA-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
- 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
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-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
- IOKWXGMNRWVQHX-VAWYXSNFSA-N (e)-1-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)-3-phenylprop-2-en-1-one Chemical compound O=[N+]1C2=CC=CC=C2N([O-])C(C)=C1C(=O)\C=C\C1=CC=CC=C1 IOKWXGMNRWVQHX-VAWYXSNFSA-N 0.000 description 1
- ZAIDIVBQUMFXEC-UHFFFAOYSA-N 1,1-dichloroprop-1-ene Chemical compound CC=C(Cl)Cl ZAIDIVBQUMFXEC-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 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
- 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
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 1
- 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
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-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
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-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
- 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
- UZYQSNQJLWTICD-UHFFFAOYSA-N 2-(n-benzoylanilino)-2,2-dinitroacetic acid Chemical compound C=1C=CC=CC=1N(C(C(=O)O)([N+]([O-])=O)[N+]([O-])=O)C(=O)C1=CC=CC=C1 UZYQSNQJLWTICD-UHFFFAOYSA-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
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical compound OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- IDPWXVBDDIYDKT-UHFFFAOYSA-N 2-phenoxyquinoline Chemical compound C=1C=C2C=CC=CC2=NC=1OC1=CC=CC=C1 IDPWXVBDDIYDKT-UHFFFAOYSA-N 0.000 description 1
- NNWTYSZJLCDUDC-UHFFFAOYSA-N 2-propoxyquinoline Chemical compound C1=CC=CC2=NC(OCCC)=CC=C21 NNWTYSZJLCDUDC-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- HQZKNCJWLIWCSV-UHFFFAOYSA-N 3,4-dichloro-1,2-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SN=C(Cl)C=1Cl HQZKNCJWLIWCSV-UHFFFAOYSA-N 0.000 description 1
- BUQPTOSHKHYHHB-UHFFFAOYSA-N 3,5-dichloropyridine-4-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C=NC=C1Cl BUQPTOSHKHYHHB-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- NHHQOYLPBUYHQU-UHFFFAOYSA-N 4-methylthiadiazole-5-carboxylic acid Chemical compound CC=1N=NSC=1C(O)=O NHHQOYLPBUYHQU-UHFFFAOYSA-N 0.000 description 1
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000024188 Andala Species 0.000 description 1
- 239000005736 Benthiavalicarb Substances 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- QCFYJCYNJLBDRT-UHFFFAOYSA-N Bis(2-chloro-1-methylethyl)ether Chemical compound ClCC(C)OC(C)CCl QCFYJCYNJLBDRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000005742 Bupirimate Substances 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 239000005746 Carboxin Substances 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 241000037488 Coccoloba pubescens Species 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000223208 Curvularia Species 0.000 description 1
- 239000005754 Cyazofamid Substances 0.000 description 1
- 239000005755 Cyflufenamid Substances 0.000 description 1
- DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 description 1
- 239000005644 Dazomet Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000005759 Diethofencarb Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 239000005764 Dithianon Substances 0.000 description 1
- 239000005765 Dodemorph Substances 0.000 description 1
- 239000005766 Dodine Substances 0.000 description 1
- 239000005767 Epoxiconazole Substances 0.000 description 1
- 241001125671 Eretmochelys imbricata Species 0.000 description 1
- 239000004258 Ethoxyquin Substances 0.000 description 1
- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 1
- 239000005772 Famoxadone Substances 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005787 Flutriafol Substances 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- 239000005959 Fosthiazate Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- FEACDOXQOYCHKU-UHFFFAOYSA-N Gougerotin Natural products CNCC(=O)NC1=NC(=O)N(C=C1)C2OC(C(O)C(NC(=O)C(N)CO)C2O)C(=O)N FEACDOXQOYCHKU-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005796 Ipconazole Substances 0.000 description 1
- 239000005797 Iprovalicarb Substances 0.000 description 1
- 239000005909 Kieselgur 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
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 239000005808 Metalaxyl-M Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 239000005810 Metrafenone Substances 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- CFZLNRGUBAVQNO-UHFFFAOYSA-N N-(3,5-Dichlorophenyl)succinimide Chemical compound ClC1=CC(Cl)=CC(N2C(CCC2=O)=O)=C1 CFZLNRGUBAVQNO-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
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 239000005814 Pencycuron Substances 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229930182764 Polyoxin Natural products 0.000 description 1
- 239000005821 Propamocarb Substances 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 239000005823 Propineb Substances 0.000 description 1
- 239000005825 Prothioconazole Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000231139 Pyricularia Species 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 1
- 241000606701 Rickettsia Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000005837 Spiroxamine Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005935 Sulfuryl fluoride Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000005840 Tetraconazole Substances 0.000 description 1
- 239000005843 Thiram Substances 0.000 description 1
- 239000005845 Tolclofos-methyl Substances 0.000 description 1
- 239000005846 Triadimenol Substances 0.000 description 1
- 239000005627 Triclopyr Substances 0.000 description 1
- 239000005858 Triflumizole Substances 0.000 description 1
- 239000005859 Triticonazole Substances 0.000 description 1
- 238000012793 UV/ Vis spectrometry Methods 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- 241000700605 Viruses 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
- 239000005870 Ziram Substances 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- BXOCHUWSGYYSFW-UHFFFAOYSA-N all-trans spilanthol Natural products CC=CC=CCCC=CC(=O)NCC(C)C BXOCHUWSGYYSFW-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229930008659 antofine Natural products 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- VVSLYIKSEBPRSN-PELKAZGASA-N benthiavalicarb Chemical compound C1=C(F)C=C2SC([C@@H](C)NC(=O)[C@@H](NC(O)=O)C(C)C)=NC2=C1 VVSLYIKSEBPRSN-PELKAZGASA-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
- 230000004071 biological effect Effects 0.000 description 1
- 229930189065 blasticidin Natural products 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- DSKJPMWIHSOYEA-UHFFFAOYSA-N bupirimate Chemical compound CCCCC1=C(C)N=C(NCC)N=C1OS(=O)(=O)N(C)C DSKJPMWIHSOYEA-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001719 carbohydrate derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 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
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 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
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 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
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- YXKMMRDKEKCERS-UHFFFAOYSA-N cyazofamid Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=C(C)C=C1 YXKMMRDKEKCERS-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 description 1
- 229960003077 cycloserine Drugs 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
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- LNJNFVJKDJYTEU-UHFFFAOYSA-N diethofencarb Chemical compound CCOC1=CC=C(NC(=O)OC(C)C)C=C1OCC LNJNFVJKDJYTEU-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 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
- JMXKCYUTURMERF-UHFFFAOYSA-N dodemorph Chemical compound C1C(C)OC(C)CN1C1CCCCCCCCCCC1 JMXKCYUTURMERF-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002085 enols Chemical group 0.000 description 1
- BBXXLROWFHWFQY-UHFFFAOYSA-N ethirimol Chemical compound CCCCC1=C(C)NC(NCC)=NC1=O BBXXLROWFHWFQY-UHFFFAOYSA-N 0.000 description 1
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019285 ethoxyquin Nutrition 0.000 description 1
- 229940093500 ethoxyquin Drugs 0.000 description 1
- BBWKDHNCTICBQA-UHFFFAOYSA-N ethyl 3,4-dichloro-1,2-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SN=C(Cl)C=1Cl BBWKDHNCTICBQA-UHFFFAOYSA-N 0.000 description 1
- AHPXTXGCMLOXGA-UHFFFAOYSA-N ethyl 4-methylthiadiazole-5-carboxylate Chemical compound CCOC(=O)C=1SN=NC=1C AHPXTXGCMLOXGA-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-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
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 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
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 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
- 238000005187 foaming Methods 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
- DUFVKSUJRWYZQP-UHFFFAOYSA-N fosthiazate Chemical compound CCC(C)SP(=O)(OCC)N1CCSC1=O DUFVKSUJRWYZQP-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 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 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 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
- 239000005414 inactive ingredient Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-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
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)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
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000002147 killing effect Effects 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 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 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000004530 micro-emulsion Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001282 organosilanes Chemical class 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
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 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
- 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
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000012809 post-inoculation Methods 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 238000012545 processing Methods 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
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-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
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 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
- 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
- 238000010791 quenching Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 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
- 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
- AVWNVTHTBTZVNI-UHFFFAOYSA-M sodium 3,4-dichloro-1,2-thiazole-5-carboxylate Chemical compound ClC1=NSC(=C1Cl)C(=O)[O-].[Na+] AVWNVTHTBTZVNI-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- CGVZLUQEQGUVML-UHFFFAOYSA-M sodium;4-methylthiadiazole-5-carboxylate Chemical compound [Na+].CC=1N=NSC=1C([O-])=O CGVZLUQEQGUVML-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 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
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229960002178 thiamazole Drugs 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 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
- 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
- 238000012384 transportation and delivery 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
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 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
- 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- NCVWJDISIZHFQS-UHFFFAOYSA-N tylophorine B Natural products C12=CC(OC)=C(OC)C=C2C2=CC(OC)=CC=C2C2=C1CC1CCCN1C2 NCVWJDISIZHFQS-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 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
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
技术领域
本发明涉及含苄基1,2,3-三唑结构的化合物及其制备方法、包含它们的农药组合物和它们在防治植物病害中的用途;具体而言,本发明涉及可抑制真菌和卵菌附着胞形成的含苄基1,2,3-三唑结构的化合物及其制备方法和在防治真菌和卵菌引起的植物病害中的用途。
背景技术
植物病害的70~80%是由真菌和卵菌引起的,一种植物上可出现几种甚至几十种不同的真菌和卵菌引起的病害。例如,水稻的纹枯病、稻瘟病、稻曲病、胡麻斑和恶苗病等,小麦的赤霉病、白粉病、条锈病、杆锈病、叶锈病、根腐病和纹枯病等,玉米的大斑病、小斑病、茎基腐、锈病、纹枯病、弯孢霉叶斑病、丝黑穗病、黑粉病等,均是真菌引起的。这些真菌病害危害面积和引起的损失占作物病害的90%以上。除真菌病害外,卵菌引起的病害在许多作物上危害严重,如马铃薯晚疫病、大豆疫霉病、辣椒疫霉病、葡萄霜霉病和黄瓜霜霉病等。
对由真菌和卵菌引起的植物病害,一般多以施用化学药剂作为主要防治手段。目前在化学防治中常用的杀菌剂包括波尔多液、百菌通、百菌清、甲基托布津、多菌灵、嘧菌酯、吡唑醚菌酯、咪鲜胺和三环唑等。其中作为保护剂使用的有波尔多液、百菌清、嘧菌酯、咪鲜胺和三环唑等,兼有保护剂和治疗剂效果的包括百菌通、甲基托布津、多菌灵和吡唑醚菌酯等。保护剂与治疗剂的分子结构多种多样,但大多数包括含氮杂环结构,其中较为常见的是嘧啶、咪唑、吡唑和1,2,4-三唑。
三氮唑类农用化合物常用的结构为1,2,4-三唑。包含该类结构的化合物包括以苯醚甲环唑和戊唑醇等为代表的内吸性杀菌剂,该类杀菌剂通过抑制病原真菌甾醇的脱甲基化来完成病害防控。目前,有关1,2,4-三唑类化合物的研究报道非常广泛,而缺乏针对1,2,3-三唑类化合物的杀菌的研究。1,2,3-三唑类化合物作为新型的具有杀菌潜力的化合物,逐渐成为杀菌剂研发的新方向。同时,1,2,3-三唑类化合物作为1,2,4-三唑类化合物的电子等排体,在农用杀菌剂领域表现出了潜在的研究价值。
由真菌和卵菌引起的病害大多数在田间主要通过无性孢子传播。其中不少真菌或卵菌的无性孢子,如稻梨孢菌和炭疽病菌分生孢子,在着陆植物体表后发芽,在发芽管顶端形成附着胞,并通过附着胞膨压进入植物组织、引起病害。附着胞是许多植物和动物病原真菌形成的一种特异侵染结构,因此,有不少研究在揭示真菌附着胞形成的分子机理,以期为绿色杀菌剂开发提供靶标。目前,生产上广泛用于稻瘟病防治的三环唑就是通过抑制稻梨孢菌附着胞的黑色素形成,从而达到控制病害的目的。但是目前抑制附着胞形成的杀菌剂种类很少,因此,创制附着胞形成的抑制剂对于研发植物真菌和卵菌病害的杀菌剂具有重大意义。
目前关于评价候选化合物杀菌活性的通用方法包括测定候选化合物对病原真菌营养菌丝生长的抑制率,进而推断其对病原真菌的防治效果。但是,该方法在很大程度上不能客观地反映候选化合物的功能,尤其是对于形成附着胞类的病原真菌和卵菌。以能形成附着胞的模式病原真菌—稻瘟菌为例,据已有文献报道,稻瘟菌营养菌丝的生长速率与其致病能力没有明显的相关性,而分生孢子萌发、芽管生长和附着胞形成和成熟直接决定稻瘟菌的致病能力。
由于自然界中的致病菌针对某种特定的杀菌剂会不断产生耐药性或者在使用过程中也会发现某些杀菌剂存在环境问题,因此,开发具有更好的应用性质的杀菌剂是本领域所面对的问题。
发明内容
针对现有技术中存在的不利之处,本发明的目的在于提供一种具有防治真菌和卵菌引起的植物病害的含苄基1,2,3-三唑结构的化合物。
因此,本发明的第一方面提供了式(I)所示的化合物、其立体异构体、消旋体、互变异构体、同位素标记物、氮氧化物、农业上可接受的盐或酯、溶剂合物或者农业上可接受的盐的溶剂合物:
,
其中,
R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、卤素、C1-C12烷基、C1-C12烷氧基或卤代C1-C12烷基。
根据本发明的实施方案,R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、卤素、C1-C3烷基、C1-C3烷氧基或卤代C1-C3烷基。
根据本发明优选的实施方案,R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、Br、Cl、F、CF3或OCH3。
在一个优选的实施方案中,R1、R2、R4和R5为H;R3为Br、Cl、F、CF3或OCH3。
在一个优选的实施方案中,R1、R4和R5为H;R2、R3相同或不同,彼此独立地选自Br、Cl、F、CF3或OCH3。
在一个优选的实施方案中,R1、R4和R5为H;R2、R3为Cl。
本发明的第二方面提供了一种农药组合物,例如杀菌剂、除草剂、植物保护剂组合物,其包含作为活性成分的式(I)的化合物、其立体异构体、消旋体、互变异构体、同位素标记物、氮氧化物、农业上可接受的盐或酯、溶剂合物或者农业上可接受的盐的溶剂合物中的一种、两种或更多种。
根据本发明的一些实施方案,所述农药组合物是杀菌剂,所述杀菌剂中含有选自式(I)的化合物和任选的农业上可接受的辅料。优选地,农药组合物作为植物保护剂,用于预防植物病害或使植物免受植物病害的侵害,所述植物病害包括稻瘟病、炭疽病、霜霉病、疫霉病和白粉病。更优选地,所述病害选自水稻稻瘟病、辣椒炭疽病、瓜类霜霉病如黄瓜霜霉病、草莓炭疽病、玉米炭疽病、马铃薯晚疫病、辣椒疫霉病和小麦白粉病。
根据本发明的一些实施方案,所述组合物中活性成分式(I)的化合物、其立体异构体、消旋体、互变异构体、同位素标记物、氮氧化物、农业上可接受的盐或酯、溶剂合物或者农业上可接受的盐的溶剂合物的重量百分含量为0.1-99.9%,例如为0.5-99%。
根据本发明的一些实施方案,所述组合物中还包括农业,和/或林业,和/或畜牧业,和/或园艺学上可接受的载体中的一种、两种或者更多种。
根据本发明的一些实施方案,所述组合物可以以制剂的形式施用。
例如,式(I)的化合物作为活性成分溶解或分散于载体中或配制成制剂以便作为除草使用时更易于分散。
根据本发明的一些实施方案,所述制剂包括但不限于如下形式:颗粒剂、可湿性粉剂、油悬剂、水悬剂、水乳剂、水剂、乳油或微胶囊等。
根据本发明的一些实施方案,所述组合物中还可以加入一种液体或固体载体,及任选的表面活性剂。
本发明的第三方面提供了式(I)的化合物、其立体异构体、消旋体、互变异构体、同位素标记物、氮氧化物、农业上可接受的盐或酯、溶剂合物或者农业上可接受的盐的溶剂合物中的一种、两种或更多种的用途,其用于防治水稻稻瘟病、辣椒炭疽病、瓜类霜霉病如黄瓜霜霉病、草莓炭疽病、玉米炭疽病、马铃薯晚疫病、辣椒疫霉病和小麦白粉病。
根据本发明的一些实施方案,本发明的式(I)的化合物、其立体异构体、消旋体、互变异构体、同位素标记物、氮氧化物、农业上可接受的盐或酯、溶剂合物或者农业上可接受的盐的溶剂合物的有效量为每公顷10克到1000克,优选有效量为每公顷20克到500克。
本发明的有益效果
本发明公开了1,2,3-三唑衍生物,其具有抑制真菌和卵菌附着胞形成的活性。且式(I)的化合物可有效地抑制真菌和卵菌的分生孢子萌发,芽管生长或附着胞的形成。
本发明人发现,1,2,3-三唑类化合物可以通过抑制分生孢子萌发,芽管生长或附着胞形成,有效阻止病菌侵染植物,进而用于防治危害巨大的植物病害,包括:稻瘟病、炭疽病、霜霉病、疫霉病和白粉病,提供了植物保护用药的新选择。
本发明人发现,本发明具有特定结构的1,2,3-三唑类化合物在10-1000ppm的浓度内即可有效抑制病原真菌和卵菌附着胞的形成。
本发明人发现,本发明具有特定结构的1,2,3-三唑类化合物在10-1000ppm的浓度内可在稻瘟病和马铃薯晚疫病的田间施用中产生相应防效。
术语和解释
除非另外指明,否则本文所有科技术语具有的含义与所属技术领域的技术人员通常理解的含义相同。除非另外指明,否则本文中以全文或部分引用的所有专利和非专利文献或以其他方式公开的材料均通过引用方式并入本文。
在本文中,在描述一个/种、两个/种或更多个/种时,“更多个/种”应当是指大于2的情形,例如代表大于等于3的整数情形,例如3、4、5、6、7、8、9或10。
在本文中,术语“任选(的/地)”表示所述特征存在或不存在这两种情形。
术语“卤素”表示氟、氯、溴和碘。
术语“C1-C12烷基”表示具有1、2、3、4、5、6、7、8、9、10、11或12个碳原子的直链和支链饱和烃基,包括甲基、乙基、正丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、2-甲基丁基、1-甲基丁基、1-乙基丙基、1,2-二甲基丙基、新戊基、1,1-二甲基丙基、正己基、4-甲基戊基、3-甲基戊基、2-甲基戊基、1-甲基戊基、2-乙基丁基、1-乙基丁基、3,3-二甲基丁基、2,2-二甲基丁基、1,1-二甲基丁基、2,3-二甲基丁基、1,3-二甲基丁基或1,2-二甲基丁基或它们的异构体。
术语“C1-C12烷氧基”指-O-C1-C12烷基,其中C1-C12烷基的定义如上段所述。烷氧基的非限制性实例包括:甲氧基、乙氧基、丙氧基、丁氧基、环丙氧基、环丁氧基、环戊氧基、环己氧基。
术语“卤代C1-C12烷基”指上述C1-C12烷基上至少一个H原子被卤素取代的情况。卤代C1-C12烷基的非限制性实例包括:三氟甲基。
应当理解,可在参考文献(包括Carey and Sundberg,"ADVANCED ORGANICCHEMISTRY 4TH ED." Vols. A (2000) and B (2001), Plenum Press, New York)中找到对标准化学术语的定义。除非另有说明,否则采用本领域技术范围内的常规方法,如质谱、NMR、IR和UV/Vis光谱法和药理学方法。除非另有具体定义,否则本文在分析化学、有机合成化学以及药物和药物化学的有关描述中采用的术语是本领域已知的。可在化学合成、化学分析、药物制备、制剂和递送,以及对患者的治疗中使用标准技术。例如,可利用厂商对试剂盒的使用说明,或者按照本领域公知的方式或本申请的说明来实施反应和进行纯化。通常可根据本说明书中引用和讨论的多个概要性和较具体的文献中的描述,按照本领域熟知的常规方法实施上述技术和方法。在本说明书中,可由本领域技术人员选择基团及其取代基以提供稳定的结构部分和化合物。
本文所用术语“农业上可接受的盐”是指保留了指定化合物的游离酸和游离碱的生物效力,并且在生物学或其它方面上没有不良作用的盐。本申请中的农业上可以接受的盐包括一般在农业、林业、畜牧业和/或园艺领域能够使用的盐,例如钠盐、钾盐、钙盐、锌盐等。农业上可接受的盐尤其是指将母体化合物中的酸性基团和/或碱性基团转换成盐的形式。
农业上可接受的盐包括,但不仅限于,衍生自酸性基团如羧基、磺基、酚羟基等的无机或有机碱盐类。根据本发明的农业上可接受的盐可以由母体化合物合成,即母体化合物中的酸性基团与适量的碱,例如1-4当量的碱在一个溶剂系统中反应;或类似地在母体化合物中存在碱性基团如氨基的情况下,与合适的无机或有机酸所成的盐类;在母体化合物既包含酸性中心(例如羧基)又包含碱性中心(例如氨基)的情况下,则其还可以形成内盐。合适的盐列举在Remingtong’s Pharmaceutical Scicences, 17thed., Mack PublishingCompany, Easton, Pa., 1985, p. 1418和Journal of Pharmaceutical Science, 66, 2(1977)中,例如钠盐。
本发明的化合物可以溶剂合物(如水合物)的形式存在,其中本发明的化合物包含作为所述化合物晶格的结构要素的极性溶剂,特别是例如水、甲醇或乙醇。极性溶剂特别是水的量可以化学计量比或非化学计量比存在。
根据其分子结构,本发明的化合物可以是手性的,因此可能存在各种对映异构体形式。因而这些化合物可以以消旋体形式或光学活性形式存在。本发明的化合物或其中间体可以通过本领域技术人员公知的化学或物理方法分离为对映异构体化合物,或者以此形式用于合成。在外消旋的胺的情况中,通过与光学活性的拆分试剂反应,从混合物制得非对映异构体。适当的拆分试剂的示例是光学活性的酸,例如R和S形式的酒石酸、二乙酰酒石酸、二苯甲酰酒石酸、扁桃酸、苹果酸、乳酸、适当的N-保护的氨基酸(例如N-苯甲酰脯氨酸或N-苯磺酰基脯氨酸)或各种光学活性的樟脑磺酸。借助光学活性的拆分试剂(例如固定在硅胶上的二硝基苯甲酰基苯基甘氨酸、三乙酸纤维素或其它碳水化合物的衍生物或手性衍生化的异丁烯酸酯聚合物),也可有利地进行色谱对映体拆分。用于此目的的适当的洗脱剂是含水或含醇的溶剂混合物,例如,己烷/异丙醇/乙腈。
术语“互变异构体”是指因分子中某一原子在两个位置迅速移动而产生的官能团异构体。本发明化合物可表现出互变异构现象。互变异构的化合物可以存在两种或多种可相互转化的种类。质子移变互变异构体来自两个原子之间共价键合的氢原子的迁移。互变异构体一般以平衡形式存在,尝试分离单一互变异构体时通常产生一种混合物,其理化性质与化合物的混合物是一致的。平衡的位置取决于分子内的化学特性。例如,在很多脂族醛和酮如乙醛中,酮型占优势;而在酚中,烯醇型占优势。本发明包含化合物的所有互变异构形式。
可以根据已知的方法,例如通过萃取、过滤或柱层析来分离相应的稳定异构体。
术语“杀菌剂”在本文中包括能够有效控制和/或杀灭对植物有害的病原微生物如细菌、真菌、卵菌、立克次氏体、支原体、病毒和/或藻类等的化学品和/或制剂。
术语“农药组合物”表示含有一种、两种或更多种本文所述化合物或其农业上可接受的盐或前体药物与其他活性或非活性组分如辅料的混合物,特别地例如含有载体和赋形剂。
由于其积极的特性,式(I)化合物可有利地用于保护耕地和非耕地中重要的作物,以及人类常去的环境免于有害病原体的侵害。
为获得理想效果,式(I)化合物的用量因各种因素而改变,例如所用化合物、预保护的作物、有害病原体的类型、感染程度、气候条件、施药方法和采用的剂型。
本文中所述剂型或组合物成分的选择应与有效成分的物理性质,应用方式和环境因素例如土壤类型,湿度与温度相一致。
有用的剂型包括液剂如溶液(包括乳油),悬浮剂,乳液(包括微乳剂和/或悬浮剂)等等,它们可任选被粘稠成胶状物。有用的剂型也包括固体的如粉剂,粉末,颗粒剂,片剂,丸剂,薄膜等,它们可以是水分散性的(“可湿的”) 或水溶性的。有效成分可被微囊化再制成悬浮剂或固体剂型;另外有效成分的整个剂型也可以成胶囊化。成胶囊可以控制或延缓释放有效成分。可喷雾剂型可在适当的介质中冲稀,使用的喷雾体积为每公顷大约一百至几百升。高浓度的组合物主要用作进一步加工的中间体。
典型的固体稀释剂在Watkins等人,Handbook of Insecticide Dust Diluentsand Carriers,2nd Ed.,Dorland Books,Caldwell,New Jersey 中作了介绍。典型的液体稀释剂在Marsden,SolventsGuide,2nd Ed.,Interscience,New York,1950 中作了介绍。McCutcheon′s Detergents and Emulsifiers Annual,Allured Publ.Corp.,Ridgewood,New Jersey,以及Sisely and Wood,Encyclopedia of Surface Active Agents,ChemicalPubl.Co.,Inc.,New York,1964,列出了表面活性剂和推荐应用。所有剂型都可含有少量的添加剂,以减少泡沫,结并,腐蚀,微生物的生长等,或加增稠剂以增加粘度。
表面活性剂包括,例如,聚乙氧基化醇,聚乙氧基化烷基酚,聚乙氧基化脱水山梨醇脂肪酸酯,磺化丁二酸二烷基酯,硫酸烷基酯,烷基苯磺酸盐,有机硅烷,N,N-二烷基牛磺酸酯,木质素磺酸盐,萘磺酸盐用醛缩合物,聚羧酸酯和聚氧乙烯/聚氧丙烯嵌段共聚物。
固体稀释剂例如包括粘土,如膨润土、蒙脱石、硅镁土、高岭土、淀粉、糖、二氧化硅、滑石、硅藻土、尿素、碳酸钙、碳酸钠、碳酸氢钠、和硫酸钠;液体稀释剂例如包括、水、N,N-二甲基甲酰胺、二甲砜、N-烷基吡咯啉酮、乙二醇、聚丙二醇、石腊、烷基苯、烷基萘、橄榄油、蓖麻油、亚麻籽油、桐油、芝麻油、玉米油、花生油、棉籽油、大豆油、菜籽油和可可油、脂肪酸酯;酮类如环己酮、2-庚酮、异佛尔酮和4-羟基-4-甲基-2-戊酮;和醇类如甲醇、环己醇、十二烷醇和四氢呋喃醇。
溶液、悬浮液、乳油等可以通过简单地混合各组分来制备。粉剂和细粉可通过混合和通常在锤磨或液能磨中通过研磨来制备悬浮剂一般通过湿磨来制备。
本文中,对于所述组合物的某些应用,例如在农业上可在本发明的组合物中加入一种、两种或多种其它的杀菌剂、杀虫杀螨剂、除草剂、植物生长调节剂、植物保护剂或肥料等,由此可产生附加的优点和效果。
式(I)化合物可以以未经改变的形式使用或优选与制剂领域中常用的载体和助剂一起使用。
因此,本发明还涉及防治或保护对抗致植物病微生物的组合物,其包含式(I)的化合物和惰性载体,以及防治或预防有用植物被致植物病微生物侵染的方法,其中将包含作为活性成分的式(I)的化合物和惰性载体的组合物施用至植物、至其部分或其处所。
为此,式(I)化合物和惰性载体以已知方式方便地配制为乳油、可包衣糊剂、可直接喷雾或可直接稀释的溶液剂、稀释乳剂、可湿性粉剂、可溶性粉剂、粉剂、颗粒剂以及例如在聚合物质中胶囊化。与组合物的类型相似地,同样根据目标对象和主要环境来选择施用方法,比如喷雾、雾化、喷粉、撒播、被覆或浇注。该组合物还可以包含其它助剂比如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂以及肥料、微量营养素供体或其它用来获得特殊效果的配制剂。
适宜的载体和助剂可以是固体或液体并且是制剂技术中有用的物质,例如天然的或经再生的矿物质、溶剂、分散剂、润湿剂、增粘剂、增稠剂、粘合剂或肥料。
制剂,也即包含式(I)化合物和根据需要的固体或液体助剂的组合物,是以已知方式制备的:通常通过将该化合物与增量剂紧密混合和/ 或磨粉,所述增量剂例如是溶剂、固体载体并任选是表面活性化合物(表面活性剂)。
农业化学制剂通常包括0.1到99%重量、优选0.1到95%重量的式(I)的化合物,99.9到1%重量、优选99.8到5%重量的固体或液体助剂,以及0到25%重量、优选0.1到25%重量的表面活性剂。
本发明所述1,2,3-三唑类衍生物可以与本领域常用的任意一种或两种或更多种农药活性成分组合,以用于防治农业和林业以及园艺植物病害。
所述农药活性成分可以选自:苯并噻二唑、噻酰菌胺、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、病毒唑、安托芬、宁南霉素、水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、萎锈灵、氧化萎锈灵、麦锈灵、甲呋酰胺、灭锈胺、氟酰胺、呋吡菌胺、噻呋酰胺、啶酰菌胺、吡噻菌胺、吡唑萘菌胺、联苯吡菌胺、氟吡菌酰胺、氟唑环菌胺、氟唑菌酰胺、氟唑菌苯胺、苯丙烯氟菌唑、异丙噻菌胺、氟唑菌酰羟胺、氟苯醚酰胺、氟醚菌酰胺、双炔酰菌胺、苯酰菌胺、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、三唑醇、灭菌唑、联苯三唑醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、多菌灵、苯菌灵、甲基硫菌灵、三唑酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、丰索磷、虫线磷、除线磷、丁硫环磷、杀线威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑等。
附图说明
图1为生物学实施例G2中化合物A-007对湘晚籼11的预防喷雾接种和治疗喷雾接种测试结果,图中从左到右分别为:在不喷雾小分子药剂下接种7天后的测试结果;A-007在接种7天后的预防喷雾接种测试结果;A-007在接种7天后的治疗喷雾接种测试结果。
图2为化合物A-003的核磁共振氢谱图。
图3为化合物A-007的核磁共振氢谱图。
具体实施方式
下文将结合具体实施例对本发明的制备方法做更进一步的详细说明。应当理解,下列实施例仅为示例性地说明和解释本发明,而不应被解释为对本发明保护范围的限制。凡基于本发明的内容所实现的技术方案均涵盖在本发明旨在保护的范围内。
除非另外指明,否则下述实施例中所使用的实验方法均为本领域常规方法;下述实施例中所使用的试剂、原料、仪器、设备等,均可从商业途径获得。
使用的试剂
除乙酸乙酯、石油醚及二氯甲烷以外,其余试剂均经过无水,无氧处理后使用。所使用的合成前体从毕得医药集团、安耐吉化学集团、阿拉丁集团购买,所使用的金属催化剂均从萨恩化学集团公司购买。
仪器和设备
用Bruker DPX500和Varian Mercury 400两种核磁共振仪测定1H、13C、19F NMR图谱,其中1H NMR和13C NMR分析中,以四甲基硅烷(TMS)作为内标,化学位移的单位均为ppm。高分辨质谱法由Bruker Apex IV FTMS spectrometer, Thermo Q-Exactive HRMS仪器进行测定。红外光谱法由Nicolet AVATAR 330 FT-IR进行测定。
通过制备实施例和生物学实施例示例性说明本发明的代表性式(I)的1,2,3-三唑类化合物的合成与生物活性及相关应用。
根据以下通用合成路线IA,本领域技术人员可以分别采用对应的本领域常规和已知的起始原料合成下表1中的各种化合物并对其进行表征。
通用合成路线IA(适用于制备下表1中的A系列编号的化合物):
将4-(4-甲基哌嗪)苯甲醛置于反应瓶中,向其中加入30.0毫升乙醇,开始搅拌,室温下缓慢加入硼氢化钠(40.0 mmol)。40摄氏度下搅拌1小时。TLC检测反应完毕,加入水和二氯甲烷萃取,饱和食盐水洗,合并有机层,无水硫酸钠干燥。有机层进行浓缩,使用柱层析进行分离,获得化合物B-A-1。
将化合物B-A-1 (20.0 mmol)置于反应瓶中,向其中加入30.0毫升二氯甲烷,搅拌下加入三乙胺(40.0 mmol)和甲基磺酰氯(30.0 mmol),室温下搅拌。TLC检测反应完毕,体系浓缩后加入30毫升N,N-二甲基甲酰胺,冰水浴下分批次加入叠氮化钠(21.0 mmol),50摄氏度下反应。TLC检测反应完毕,加入水和二氯甲烷萃取,饱和食盐水洗,合并有机层,无水硫酸钠干燥。有机层进行浓缩,使用柱层析进行分离,获得化合物B-A-2。
将取代的苯酚(20.0 mmol)置于反应瓶中,向其中加入30.0毫升丙酮,搅拌下加入碳酸钾(40.0 mmol),3-溴丙炔(21.0 mmol),TLC检测反应完毕。过滤,将滤液减压浓缩,柱层析分离残余物,获得化合物B-A-3。
将化合物B-A-3(10.0 mmol)置于反应瓶中,向其中加入8.0毫升N,N-二甲基甲酰胺,搅拌下加入五水硫酸铜(2.0 mmol),叠氮化合物B-A-2 (11.0 mmol),抗坏血酸钠(20.0mmol)和2.0毫升水。TLC检测反应完毕,过滤,将滤液浓缩后加入水和二氯甲烷萃取,饱和食盐水洗,合并有机层,无水硫酸钠干燥,浓缩,柱层析分离残余物,获得下表1中的A系列编号的化合物。
化合物实施例
实施例1
第一步:
取1.0克化合物a-1于反应瓶中,加入10毫升无水乙醇,开始搅拌,室温下缓慢加入373毫克硼氢化钠,40摄氏度下搅拌1小时。TLC检测反应完毕,加入20毫升水,再使用20毫升二氯甲烷萃取三次,合并有机层,使用30毫升饱和氯化钠溶液洗涤有机层,使用无水硫酸钠进行干燥。有机层进行浓缩,使用柱层析进行分离,得到0.81克化合物a-2。
第二步:
取1.0克化合物a-2于反应瓶中,加入10毫升二氯甲烷,搅拌下滴加1.35毫升三乙胺和0.57毫升甲基磺酰氯,室温反应1.5小时。TLC检测反应完毕,体系浓缩后加入10毫升N,N-二甲基甲酰胺,冰水浴下缓慢加入331毫克叠氮化钠,50摄氏度下反应。反应12小时后TLC检测反应完毕,加入30毫升水淬灭反应,使用30毫升二氯甲烷萃取三次,有机层合并加入30毫升饱和氯化钠溶液洗涤,随后加入无水硫酸钠干燥。柱层析分离得到570毫克化合物a-3。
第三步:
取0.50克化合物a-4于反应瓶中,加入10毫升丙酮,搅拌下加入1.47克碳酸钾,665毫克3-溴丙炔,回流反应,TLC检测反应完毕。过滤,减压浓缩,柱层析分离得594毫克化合物a-5。
第四步:
取250毫克化合物a-5于反应瓶中,加入4.0毫升N,N-二甲基甲酰胺,搅拌下加入95毫克五水硫酸铜,481毫克化合物a-3,750毫克抗坏血酸钠和1.0毫升水,50摄氏度反应,TLC检测反应完毕。过滤,浓缩后加入水和二氯甲烷萃取,饱和食盐水洗合并有机层,无水硫酸钠干燥,柱层析分离得509毫克化合物A-001。
以类似于实施例1的方法,参考通用合成路线IA,通过对原料进行替换,获得下表1中以A编号的化合物。
表1
化合物 | <![CDATA[R<sub>1</sub>]]> | <![CDATA[R<sub>2</sub>]]> | <![CDATA[R<sub>3</sub>]]> | <![CDATA[R<sub>4</sub>]]> | <![CDATA[R<sub>5</sub>]]> |
A-002 | H | H | Br | H | H |
A-003 | H | H | Cl | H | H |
A-004 | H | H | F | H | H |
A-005 | H | H | <![CDATA[CF<sub>3</sub>]]> | H | H |
A-006 | H | H | <![CDATA[OCH<sub>3</sub>]]> | H | H |
A-007 | H | Cl | Cl | H | H |
表2:化合物结构表征数据
表2显示化合物A-001及表1中所列出的化合物的质谱数据和1H-NMR数据。除非另有说明,否则将氘代氯仿(CDCl3)或氘代二甲亚砜(DMSO
-d 6)用作测试溶剂。
在表2以及下文的全部描述中,“NMR”意指核磁共振谱,MS代表质谱。并使用下述缩写:
s = 单峰,br = 宽峰,d = 双峰,dd = 双二重峰,t = 三重峰,td = 三二重峰,q= 四重峰,m = 多重峰。
表2
化合物 | <![CDATA[<sup>1</sup>H-NMR数据]]> | <![CDATA[MS[M+H]<sup>+</sup><!-- 10 -->]]> |
A-001 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.51 (s,1H), 7.31 – 7.25 (m,2H), 7.21 (d, <i>J</i> = 8.2Hz, 2H), 7.00 – 6.92(m, 3H), 6.89 (d, <i>J</i>= 8.2 Hz, 2H), 5.44(s, 2H), 5.16 (s, 2H),3.52 – 3.38 (m, 4H),3.03 – 2.87 (m, 4H),2.61 (s, 3H).]]> | 364.23 |
A-002 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.47 (s,1H), 7.38 – 7.34 (m,2H), 7.22 – 7.18 (m,2H), 6.92 – 6.88 (m,2H), 6.87 – 6.82 (m,2H), 5.44 (s, 2H),5.14 (s, 2H), 3.45 –3.39 (m, 4H), 2.98 –2.81 (m, 4H), 2.58(s, 3H).]]> | 442.11 |
A-003 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.47 (s,1H), 7.24 – 7.18 (m,4H), 6.92 – 6.87 (m,4H), 5.44 (s, 2H),5.13 (s, 2H), 3.42 –3.35 (m, 4H), 2.90 –2.76 (m, 4H), 2.53 (s,3H).]]> | 398.18 |
A-004 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.48 (s,1H), 7.23 – 7.18 (m,2H), 6.99 – 6.93 (m,2H), 6.92 – 6.87 (m,4H), 5.44 (s, 2H),5.13 (s, 2H), 3.47 –3.39 (m, 4H), 2.98 –2.83 (m, 4H), 2.59 (s,3H).]]> | 382.21 |
A-005 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.53 (d, <i>J</i> =8.7 Hz, 2H), 7.50 (s,1H), 7.22 – 7.19 (m,2H), 7.03 (d, <i>J</i> = 8.7Hz, 2H), 6.92 – 6.88(m, 2H), 5.45 (s, 2H),5.21 (s, 2H), 3.43 –3.37 (m, 4H), 2.98 –2.77 (m, 4H), 2.56 (s,3H).]]> | 432.22 |
A-006 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.47 (s,1H), 7.23 – 7.18 (m,2H), 6.92 – 6.88 (m,4H), 6.84 – 6.80 (m,2H), 5.44 (s, 2H),5.12 (s, 2H), 3.76 (s,3H), 3.48 – 3.33 (m,4H), 3.01 – 2.74 (m,4H), 2.56 (s, 3H).]]> | 394.24 |
A-007 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.47 (s,1H), 7.31 (d, <i>J</i> = 8.8Hz, 1H), 7.20 (d, <i>J</i> =8.3 Hz, 2H), 7.06(d, <i>J</i> = 3.0 Hz, 1H),6.90 (d, <i>J</i> = 8.3 Hz,2H), 6.83 (dd, <i>J</i> =8.8, 3.0 Hz, 1H), 5.44(s, 2H), 5.13 (s, 2H),3.41 – 3.32 (m, 4H),2.85 – 2.72 (m, 4H),2.51 (s, 3H).]]> | 432.14 |
生物学实施例
鉴于稻瘟菌通常经由附着胞介导侵染植物的模式及能在室内人工培养,因此可以以稻瘟菌为模型病原真菌进行本发明化合物对稻瘟菌分生孢子萌发、芽管生长或附着胞形成抑制测试。通过以下实施例示例性说明本发明化合物的相关活性。
生物学实施例G1:含苄基结构的1,2,3-三唑类化合物对稻瘟菌分生孢子萌发和附着胞形成的抑制作用
a.待测病菌:稻瘟菌(
Magnaporthe oryzae)菌株P131
b.试验方法:
1)稻瘟菌分生孢子的产生:将待测的稻瘟菌菌株P131点接到西红柿燕麦平板(OTA)上,置于28℃恒温光照培养箱培养。3-5天后将OTA上的稻瘟菌菌落充分打断,然后均匀地涂布到新的OTA上,于28℃恒温光照培养箱培养。当肉眼可见新生菌丝长出培养基表面时(一般为1-2天),用棉签轻轻将菌丝打断,并用灭菌水冲洗干净,晾干。用单层纱布盖上培养皿,于28℃光照培养48小时,在OTA表面产生大量的分生孢子。
2)配制稻瘟菌分生孢子悬浮液:用无菌水将OTA上的培养物洗脱下来,用三层擦镜纸过滤,滤液为分生孢子液。用血球计数板将分生孢子液中的分生孢子浓度调整为2小105个/mL。
3)将待测化合物按不同浓度梯度加入到分生孢子悬浮液中,分别配制成工作浓度为200ppm,50ppm和25ppm的溶液,并依次点在疏水玻片上。每个玻片上点接四个点,黑暗保湿处理。接种12小时后在显微镜下观察并计数分生孢子萌发率和附着胞形成率。
4)统计与分析:每个疏水玻片计数三个接种点,每个接种点计数其中心的100个分生孢子的萌发个数和附着胞形成个数。计算三组数据平均值,得出分生孢子萌发率和附着胞形成率。
表3显示本发明化合物的生物学实施例G1的数据,其中“-”代表在200ppm无抑制效果,“+”代表200ppm抑制效果低于40%,“++”代表在50ppm抑制效果高于40%,“+++”代表25ppm抑制效果大于70%。
表3
化合物 | 分生孢子萌发 | 附着胞形成 |
A-001 | + | + |
A-002 | + | + |
A-003 | ++ | +++ |
A-004 | + | + |
A-005 | - | + |
A-006 | + | ++ |
A-007 | +++ | +++ |
生物学实施例G2:含苄基1,2,3-三唑结构的化合物对稻瘟病的预防和治疗作用—水稻盆栽实验
水稻的准备:准备感病品种CO39和湘晚籼11,取四叶一心的水稻幼苗置于接种箱中待用。
稻瘟菌分生孢子的产生:将稻瘟菌菌株P131点接到西红柿燕麦平板(OTA)上,置于28℃恒温光照培养箱培养。3-5天后将OTA上的稻瘟菌菌落充分打断,然后均匀地涂布到新的OTA上,于28℃恒温光照培养箱培养。当肉眼可见新生菌丝长出培养基表面时(一般为1-2天),用棉签轻轻将菌丝打断,并用灭菌水冲洗干净,晾干。用单层纱布盖上培养皿,于28℃光照培养48小时,即在OTA表面产生大量的分生孢子。
配制稻瘟菌分生孢子悬浮液:用无菌水将OTA上的培养物洗脱下来,用三层擦镜纸过滤,滤液为分生孢子液。5000rpm室温离心5分钟。将沉淀的分生孢子悬浮于明胶中,用血球计数板将分生孢子浓度调整为5×104个/mL。
待测化合物溶液的制备:将待测化合物母液加入到制备好的稻瘟菌分生孢子液中,稀释至其为200ppm的工作浓度;将待测化合物母液稀释至其为200ppm的工作浓度。
预防喷雾接种:将稻瘟菌分生孢子与小分子药剂的混合物喷雾接种水稻感病品种湘晚籼11和CO39,每个处理喷雾15mL混合物。黑暗保湿培养36小时,然后进行正常培养。接种7天后,评价待测化合物对稻瘟病的预防效果(表4)。
治疗喷雾接种:将稻瘟菌分生孢子喷雾接种水稻感病品种湘晚籼11,每个处理喷雾15mL小分子药剂。黑暗保湿培养36小时,然后进行正常培养。接种7天后,评价待测化合物对稻瘟病的治疗效果(表5)。
参照农业行业标准“水稻稻瘟病抗性田间监测技术规程”(NYT3685-2020)进行稻瘟病叶瘟病害调查,具体标准如下:0级:全叶片无病;1级:叶片上有针尖大小的褐色坏死斑;2级:叶片上有较大(直径1mm~2mm)的褐色坏死斑,但无典型的病斑;3级:有典型的稻瘟病病斑,病斑面积<2%;4级:有典型的稻瘟病病斑,2%≤病斑面积<5%;5级:有典型的稻瘟病病斑,5%≤病斑面积<10%;6级:有典型的稻瘟病病斑,10%≤病斑面积<25%;7级:有典型的稻瘟病病斑,25%≤病斑面积<50%;8级:有典型的稻瘟病病斑,50%≤病斑面积<75%;9级:有典型的稻瘟病病斑,病斑面积≥75%。
表4显示本发明化合物的生物学实施例G2的数据。
表4
化合物 | 病害等级 |
A-001 | 4 |
A-002 | 3 |
A-003 | 1 |
A-004 | 5 |
A-005 | 7 |
A-006 | 2 |
A-007 | 0 |
表5显示本发明化合物的生物学实施例G2的数据。
表5
化合物 | 病害等级 |
A-001 | 6 |
A-002 | 7 |
A-003 | 6 |
A-004 | 7 |
A-005 | 7 |
A-006 | 6 |
A-007 | 5 |
生物学实施例G3:含苄基1,2,3-三唑结构的化合物对小麦白粉病的防治作用—小麦盆栽实验
小麦的准备:“小偃6号”感白粉病品种小麦幼苗正常培养至2叶期后置于接种箱中待用。同时准备已感染白粉菌系63号的“小偃6号”小麦幼苗,继续进行培养。
喷雾工作液的制备:将待测化合物母液加入水中,稀释至其为200ppm的工作浓度。
喷雾接种:将喷雾工作液喷施于小麦幼苗,喷雾后放置阴凉处自然晾干。将发病小麦叶片上24小时内产生的白粉病菌新鲜孢子均匀抖落接种于处理的盆栽小麦苗,每处理3盆,每盆10株。之后置于适宜条件继续培养。接种6天后评价待测化合物的防治效果。
表6显示本发明化合物的生物学实施例G3的数据,参照分级标准对小麦白粉病病情进行病害调查,具体标准如下:0级:无病;1级:病斑面积占整片叶面积的5%以下;3级:病斑面积占整片叶面积的6%~15%;5级:病斑面积占整片叶面积的16%~25%;7级:病斑面积占整片叶面积的26%~50%;9级:病斑面积占整片叶面积的50%以上。
表6
化合物 | 病害等级 |
A-001 | 5 |
A-002 | 3 |
A-003 | 3 |
A-004 | 3 |
A-005 | 7 |
A-006 | 3 |
A-007 | 1 |
由上述结果可知,本发明化合物对稻瘟菌分生孢子萌发和附着胞的形成具有抑制作用,且化合物A-007抑制效果明显最优。在对水稻叶片稻瘟病的喷雾接种试验中,本发明化合物具有明显的治疗效果。本发明化合物对稻瘟病不仅具有好的预防效果,还具有一定的治疗效果。
Claims (10)
1.式(I)所示的化合物:
,
其中,
R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、卤素、C1-C12烷基、C1-C12烷氧基或卤代C1-C12烷基。
2.根据权利要求1所述的化合物,其特征在于,R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、卤素、C1-C3烷基、C1-C3烷氧基或卤代C1-C3烷基。
3.根据权利要求1或2所述的化合物,其特征在于,R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、Br、Cl、F、CF3或OCH3。
4.根据权利要求3所述的化合物,其特征在于,R1、R2、R4和R5为H;R3为Br、Cl、F、CF3或OCH3。
5.根据权利要求3所述的化合物,其特征在于,R1、R4和R5为H;R2、R3相同或不同,彼此独立地选自Br、Cl、F、CF3或OCH3。
6.根据权利要求3所述的化合物,其特征在于,R1、R4和R5为H;R2、R3为Cl。
7.一种农药组合物,其特征在于,包含作为活性成分的权利要求1-6任一项所述的化合物。
8.根据权利要求7所述的农药组合物,其特征在于,所述农药组合物作为植物保护剂用于预防植物病害或使植物免受植物病害的侵害,所述植物病害包括:稻瘟病、炭疽病、霜霉病、疫霉病和白粉病。
9.根据权利要求8所述的农药组合物,其特征在于,所述植物病害选自:水稻稻瘟病、辣椒炭疽病、瓜类霜霉病、草莓炭疽病、玉米炭疽病、马铃薯晚疫病、辣椒疫霉病和小麦白粉病。
10.根据权利要求7-9任一项所述的农药组合物,其特征在于,所述组合物中活性成分式(I)所示的化合物的重量百分含量为0.1-99.9%。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211587729.4A CN115594641B (zh) | 2022-12-12 | 2022-12-12 | 一类含苄基1,2,3-三唑结构的化合物及其作为杀菌剂的应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211587729.4A CN115594641B (zh) | 2022-12-12 | 2022-12-12 | 一类含苄基1,2,3-三唑结构的化合物及其作为杀菌剂的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN115594641A CN115594641A (zh) | 2023-01-13 |
CN115594641B true CN115594641B (zh) | 2023-05-02 |
Family
ID=84852049
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202211587729.4A Active CN115594641B (zh) | 2022-12-12 | 2022-12-12 | 一类含苄基1,2,3-三唑结构的化合物及其作为杀菌剂的应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN115594641B (zh) |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1248578C (zh) * | 2003-08-29 | 2006-04-05 | 湖北省农业科学院植保土肥研究所 | 蒽醌衍生物作为防治植物病害农药的应用 |
US8278340B2 (en) * | 2007-11-27 | 2012-10-02 | North Carolina State University | Inhibition of biofilms in plants with imidazole derivatives |
GB0807138D0 (en) * | 2008-04-18 | 2008-05-21 | Syngenta Participations Ag | Novel microbiocides |
US20180263243A1 (en) * | 2015-09-25 | 2018-09-20 | Flechsig Patent Company Llc | Novel plant protecting compositions and uses thereof |
CN109627206B (zh) * | 2019-01-11 | 2022-04-12 | 贵州大学 | 一类具有手性中心的咔唑基异丙醇胺衍生物的制备方法和应用 |
-
2022
- 2022-12-12 CN CN202211587729.4A patent/CN115594641B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
CN115594641A (zh) | 2023-01-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104602523B (zh) | 保护耕种作物的增效组合物及其用途 | |
CN110300522A (zh) | 用于防治有害微生物的包含1-(苯氧基-吡啶基)-2-(1,2,4-三唑-1-基)-乙醇衍生物的组合物 | |
JP2818676B2 (ja) | 抗真菌性カルビノール | |
US20180000089A1 (en) | Novel microbiocides | |
JP2023528173A (ja) | ミトコンドリアチトクロムbタンパク質中にQo阻害剤IIに対して耐性を付与するアミノ酸置換F129Lを含む植物病原性菌類を駆除するためのストロビルリン型化合物の使用 | |
JP2023527661A (ja) | ミトコンドリアチトクロムbタンパク質中にQo阻害剤IVに対して耐性を付与するアミノ酸置換F129Lを含む植物病原性菌類を駆除するためのストロビルリン型化合物の使用 | |
JP2023527959A (ja) | ミトコンドリアチトクロムbタンパク質中にQo阻害剤IIIに対して耐性を付与するアミノ酸置換F129Lを含む植物病原性菌類を駆除するためのストロビルリン型化合物の使用 | |
JP2023527660A (ja) | ミトコンドリアチトクロムbタンパク質中にQo阻害剤Iに対して耐性を付与するアミノ酸置換F129Lを含む植物病原性菌類を駆除するためのストロビルリン型化合物の使用 | |
EA004574B1 (ru) | Оксимные о-эфирные соединения и фунгициды для применения в земледелии и садоводстве | |
CN115594641B (zh) | 一类含苄基1,2,3-三唑结构的化合物及其作为杀菌剂的应用 | |
CN109232534B (zh) | 含杂环二芳胺基吡唑甲酰胺类化合物及其制备方法与应用 | |
CN113880840A (zh) | 一种喹啉酚类衍生物或其作为农药可接受的盐、组合物及其用途 | |
CN115052869A (zh) | 取代的噻吩甲酰胺及其衍生物 | |
TW201629047A (zh) | 新穎三唑衍生物 | |
CN105777640B (zh) | 一种吡唑环己二醇醚类化合物及其应用 | |
CN116768806A (zh) | 取代的1,2,3-三唑类化合物及其制备方法和在防治植物病害中的用途 | |
WO2017008583A1 (zh) | 一类含二苯醚结构的吡唑酰胺化合物、其制备方法及应用 | |
CN118164880A (zh) | 联苯三氟乙硫醚化合物及其应用 | |
CN112661732A (zh) | 呋喃酚衍生物及其制备方法与应用 | |
TW201841906A (zh) | 新穎三唑衍生物 | |
WO2016021615A1 (ja) | 新規化合物及びその製造方法、農園芸用殺菌剤 | |
JPH02295962A (ja) | フェニルカーバゼート誘導体及びそれを含有する農園芸用殺菌剤 | |
JPWO2004035560A1 (ja) | ピロール誘導体及び中間体及び農園芸用殺菌剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |