CN116349683A - Fungicidal composition containing substituted triazolinone ether compound and application thereof - Google Patents
Fungicidal composition containing substituted triazolinone ether compound and application thereof Download PDFInfo
- Publication number
- CN116349683A CN116349683A CN202111612888.0A CN202111612888A CN116349683A CN 116349683 A CN116349683 A CN 116349683A CN 202111612888 A CN202111612888 A CN 202111612888A CN 116349683 A CN116349683 A CN 116349683A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- methyl
- acid
- general formula
- active component
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 67
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 17
- -1 triazolinone ether compound Chemical class 0.000 title claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 7
- 229960005437 etoperidone Drugs 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 239000003899 bactericide agent Substances 0.000 claims abstract description 21
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
- 239000003112 inhibitor Substances 0.000 claims abstract description 17
- 241000221785 Erysiphales Species 0.000 claims abstract description 16
- 241000233679 Peronosporaceae Species 0.000 claims abstract description 9
- 208000031888 Mycoses Diseases 0.000 claims abstract description 5
- 241000233647 Phytophthora nicotianae var. parasitica Species 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 230000004060 metabolic process Effects 0.000 claims description 17
- 108020004707 nucleic acids Proteins 0.000 claims description 17
- 102000039446 nucleic acids Human genes 0.000 claims description 17
- 150000007523 nucleic acids Chemical class 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 239000005807 Metalaxyl Substances 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 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 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 239000005742 Bupirimate Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- DSKJPMWIHSOYEA-UHFFFAOYSA-N bupirimate Chemical compound CCCCC1=C(C)N=C(NCC)N=C1OS(=O)(=O)N(C)C DSKJPMWIHSOYEA-UHFFFAOYSA-N 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- YYXSCUSVVALMNW-FOWTUZBSSA-N pyriminostrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC(C(F)(F)F)=NC(NC=2C(=CC(Cl)=CC=2)Cl)=N1 YYXSCUSVVALMNW-FOWTUZBSSA-N 0.000 claims description 10
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 239000005734 Benalaxyl Substances 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 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 claims description 8
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 239000005808 Metalaxyl-M Substances 0.000 claims description 7
- 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 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 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 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 244000000004 fungal plant pathogen Species 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 241000233629 Phytophthora parasitica Species 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 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 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- 230000003032 phytopathogenic effect Effects 0.000 abstract description 2
- 241000918585 Pythium aphanidermatum Species 0.000 abstract 1
- 230000002503 metabolic effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 19
- 235000002566 Capsicum Nutrition 0.000 description 12
- 240000008067 Cucumis sativus Species 0.000 description 11
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 10
- 230000002195 synergetic effect Effects 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 8
- 235000002597 Solanum melongena Nutrition 0.000 description 8
- 244000061458 Solanum melongena Species 0.000 description 8
- 239000006002 Pepper Substances 0.000 description 7
- 235000016761 Piper aduncum Nutrition 0.000 description 7
- 240000003889 Piper guineense Species 0.000 description 7
- 235000017804 Piper guineense Nutrition 0.000 description 7
- 235000008184 Piper nigrum Nutrition 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- 240000003768 Solanum lycopersicum Species 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000001717 pathogenic effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000219112 Cucumis Species 0.000 description 4
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 4
- 244000052769 pathogen Species 0.000 description 4
- 241000233866 Fungi Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 241000758706 Piperaceae Species 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 244000291564 Allium cepa Species 0.000 description 2
- 240000008574 Capsicum frutescens Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 2
- 239000001390 capsicum minimum Substances 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 235000006667 Aleurites moluccana Nutrition 0.000 description 1
- 240000006108 Allium ampeloprasum Species 0.000 description 1
- 235000005254 Allium ampeloprasum Nutrition 0.000 description 1
- 235000010167 Allium cepa var aggregatum Nutrition 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 240000002234 Allium sativum Species 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 239000005735 Benalaxyl-M Substances 0.000 description 1
- 235000011274 Benincasa cerifera Nutrition 0.000 description 1
- 244000036905 Benincasa cerifera Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- 235000009467 Carica papaya Nutrition 0.000 description 1
- 240000006432 Carica papaya Species 0.000 description 1
- 235000018244 Castanea mollissima Nutrition 0.000 description 1
- 240000004957 Castanea mollissima Species 0.000 description 1
- 235000004391 Chenopodium capitatum Nutrition 0.000 description 1
- 244000038022 Chenopodium capitatum Species 0.000 description 1
- 244000241235 Citrullus lanatus Species 0.000 description 1
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- 241000219130 Cucurbita pepo subsp. pepo Species 0.000 description 1
- 235000003954 Cucurbita pepo var melopepo Nutrition 0.000 description 1
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 1
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003956 Luffa Nutrition 0.000 description 1
- 244000050983 Luffa operculata Species 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 240000002624 Mespilus germanica Species 0.000 description 1
- 235000017784 Mespilus germanica Nutrition 0.000 description 1
- 235000000560 Mimusops elengi Nutrition 0.000 description 1
- 235000009811 Momordica charantia Nutrition 0.000 description 1
- 235000009812 Momordica cochinchinensis Nutrition 0.000 description 1
- 240000001740 Momordica dioica Species 0.000 description 1
- 235000018365 Momordica dioica Nutrition 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 235000019095 Sechium edule Nutrition 0.000 description 1
- 240000007660 Sechium edule Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000007837 Vangueria infausta Nutrition 0.000 description 1
- 235000010726 Vigna sinensis Nutrition 0.000 description 1
- 244000042314 Vigna unguiculata Species 0.000 description 1
- 241000219094 Vitaceae 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
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- CJPQIRJHIZUAQP-MRXNPFEDSA-N benalaxyl-M Chemical compound CC=1C=CC=C(C)C=1N([C@H](C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-MRXNPFEDSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- IZBNNCFOBMGTQX-UHFFFAOYSA-N etoperidone Chemical class O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 IZBNNCFOBMGTQX-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 235000021332 kidney beans Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 108020004418 ribosomal RNA Proteins 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—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
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention belongs to the field of agricultural bactericides, and in particular relates to a fungicidal composition and application thereof. The composition comprises A, B two active components, wherein the weight ratio of the active component A to the active component B is 1:99-99:1; the active component A is selected from compounds shown in the following general formula I and salts thereof, and the active component B is selected from accounting metabolic inhibitor bactericides. The fungicidal composition of the present invention is particularly suitable for controlling a variety of phytopathogenic fungal diseases such as downy mildew, late blight, epidemic disease, black shank, damping-off or powdery mildew.
Description
Technical Field
The invention belongs to the field of agricultural bactericides, and in particular relates to a fungicidal composition of a substituted triazolinone ether compound and a nucleic acid metabolism inhibitor bactericide and application thereof.
Background
Patent CN102336744B discloses a compound containing substituted triazolinone ether and its use, wherein the compound shown in the following general formula I is reported to have good activity against various fungal diseases.
The nucleic acid metabolism inhibitor bactericide inhibits the synthesis of protein and ribosomal RNA in fungi by affecting the activity of endogenous RNA polymerase, and has the function characteristics of effectively inhibiting invasion of pathogenic spores (cysts) and having the functions of protection, treatment and eradication. However, the bactericidal agent has single action site and is easy to generate resistance after long-term single use.
Disclosure of Invention
The invention aims to provide a fungicidal synergistic composition of a substituted triazolinone ether compound and a nucleic acid metabolism inhibitor bactericide and application thereof.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a fungicidal composition comprising A, B two active components, wherein the weight ratio of active component A to active component B is 1:99-99:1;
the active component A is a compound shown in a general formula I or a salt thereof.
Wherein:
q is selected from Q1 or Q2 as shown below:
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen, halogen, cyano, nitro, CH 2 CN, C1-C6 alkyl, halogenated C1-C6 alkyl or C3-C6 cycloalkyl, R 3 Selected from hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl;
when Q is selected from Q2: r is R 2 Selected from halogen, C1-C6 alkyl, halogenated C1-C6 alkyl or C3-C6 cycloalkyl, R 3 Selected from C1-C6 alkyl or halogenated C1-C6 alkyl;
R 4 selected from halogen, cyano, nitro, hydroxy, C1-C4 alkyl, halo C1-C3 alkyl, C1-C3 alkoxy, halo C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfonyl, phenyl or phenoxy, unsubstituted or substituted with 1 to 5 groups independently selected from chloro, bromo, fluoro, nitro, cyano, trifluoromethyl, C1-C3 alkyl, C1-C3 alkoxy or halo C1-C3 alkoxy; n=0-5;
R 5 、R 6 can be identical or different and is selected from hydrogen, halogen, nitro, cyano, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, phenyl, pyridyl, furyl, thienyl or thiazolyl, which are unsubstituted or substituted by 1 to 5 radicals independently selected from halogen, cyano, nitro, CO 2 (C1-C4 alkyl), C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6-C6 alkylthio or C1-C6 alkylsulfonyl;
y is selected from halogen, OR 7 、SR 7 、SOR 7 、SO 2 R 7 Or NHR 7 The method comprises the steps of carrying out a first treatment on the surface of the Wherein R is 7 Selected from hydrogen or C1-C4 alkyl;
the active component B is selected from one or more of metalaxyl B1, metalaxyl B2, bupirimate B3, pyriminostrobin B4, pyriminostrobin B5, benalaxyl B6, benalaxyl B7, furalaxyl B8, furalamide B9, oxadixyl B10, xin Saitong B11 and quinidone B12 serving as nucleic acid metabolism inhibitor bactericides.
Preferably, the active component A is selected from compounds represented by the general formula I or salts thereof.
In the general formula:
q is selected from Q1 or Q2 as shown below:
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen, fluorine, chlorine, bromine or C1-C4 alkyl, R 3 Selected from hydrogen or C1-C6 alkyl;
when Q is selected from Q2: r is R 2 Selected from C1-C4 alkyl, R 3 Selected from C1-C6 alkyl;
R 4 selected from halogen, cyano, nitro, C1-C4 alkyl, halogenated C1-C3 alkyl, C1-C3 alkoxy, halogenated C1-C3 alkoxy or C1-C3 alkylsulfonyl;
n＝0-3；
R 5 、R 6 which may be the same or different, are each selected from hydrogen, chlorine, bromine, fluorine, nitro, cyano, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy or halogenated C1-C4 alkoxy;
y is selected from Cl, OR 7 Or SR (S.J) 7 The method comprises the steps of carrying out a first treatment on the surface of the Wherein R is 7 Selected from C1-C4 alkyl;
the salt of the compound shown in the general formula I is the salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid and fumaric acid;
the active component B is selected from one or more of metalaxyl B1, bupirimate B3, pyriminostrobin B4, pyriminostrobin B5, benalaxyl B6, metalaxyl B7, furalaxyl B8, furalamide B9, oxadixyl B10 and quinidone B12 serving as nucleic acid metabolism inhibitor bactericides;
A. the weight ratio of the two active components is 1:50-50:1.
Further preferably, the active component A is selected from the group consisting of compounds of formula I or salts thereof.
In the general formula:
q is selected from Q1 or Q2;
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen or methyl, R 3 Selected from hydrogen, methyl or ethyl;
when Q is selected from Q2: r is R 2 Selected from methyl, R 3 Selected from methyl;
R 4 selected from halogen, cyano, nitro, methyl, ethyl, isopropyl, t-butyl, CF 3 、CH 3 O or CF 3 O；
n＝0-3；
R 5 、R 6 May be the same or different and are each selected from hydrogen, chlorine, bromine, fluorine or C1-C4 alkyl;
y is selected from Cl, CH 3 O or CH 3 S；
The salt of the compound shown in the general formula I is the salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid and benzoic acid;
the active component B is selected from one or more of metalaxyl B1, pyriminostrobin B4, bupirimate B5, benalaxyl B6, metalaxyl B7, furalamide B9, oxadixyl B10 and quinidone B12 serving as nucleic acid metabolism inhibitor bactericides;
the weight ratio of the A, B active components is 1:20-20:1.
Still further preferably, the active ingredient a is selected from the group consisting of compounds of formula I or salts thereof.
In the general formula:
q is selected from Q2;
w is selected from O;
R 1 selected from methyl;
R 2 selected from methyl, R 3 Selected from methyl;
R 4 selected from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, CF 3 、CH 3 O or CF 3 O；
n=0, 1, 2 or 3;
R 5 、R 6 may be the same or different and are each selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl or isopropyl;
y is selected from Cl or CH 3 O；
The salt of the compound shown in the general formula I is a salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid and acetic acid;
the active component B is selected from one or more of metalaxyl B1, pyriminobac-methyl B4, bupirimate B5, metalaxyl B7, oxadixyl B10 and quinidone B12 serving as nucleic acid metabolism inhibitor bactericides;
the weight ratio of the A, B active components is 1:10-10:1.
Still further preferably, the active ingredient a is selected from the group consisting of compounds of formula I or salts thereof.
In the general formula:
q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; n=0; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O)；
Or Q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; r is R 4 Selected from fluorine; n=1; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O)；
Or Q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; r is R 4 Selected from chlorine; n=1; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O)；
The salt of the compound shown in the general formula I is a salt formed by the compound shown in the general formula I, hydrochloric acid and sulfuric acid;
the active component B is selected from one or more of metalaxyl-M B1, bupirimate B5 and metalaxyl-M B7 serving as nucleic acid metabolism inhibitor bactericides;
the weight ratio of the A, B active components is 1:4-4:1.
Use of a fungicidal composition for the preparation of a medicament for controlling phytopathogenic fungal diseases.
The plant pathogenic fungus disease is plant downy mildew, late blight, epidemic disease, black shank, damping-off or powdery mildew.
The composition of the present invention is used at a concentration of 5 to 500mg/L (active ingredient content, the same applies hereinafter) in the crop planting area, preferably 50 to 200mg/L, depending on the occurrence degree of crop diseases.
The composition of the invention comprises an active component A and at least one active component B which are prepared in advance or prepared on the site of use according to the proper proportion provided by the invention or the two components are used separately and sequentially.
The composition of the invention is suitable for the prevention and treatment of fungi diseases of trees (apples, rubber, pears, citrus, haws, chinese chestnut, peppers, medlar, mangoes, papaya and the like), vines (grapes), melons (tomatoes, eggplants, peppers, cucumbers, melons, white gourd, watermelons, pumpkins, balsam pears, luffa, chayote, cucurbits, zucchini, carrots, lettuce, potatoes), beans (peas, kidney beans, cowpea), cereals (wheat), shallots and garlic (onions ), spinach, cabbages, tobacco, strawberries, flowers and lawns.
The fungicidal compositions according to the invention are particularly suitable for controlling the following plant diseases: tomato late blight, potato black shank, capsicum blight, leek blight, melon downy mildew, vegetable downy mildew, grape downy mildew, strawberry blight, ornamental plant blight, melon powdery mildew, bean powdery mildew, eggplant powdery mildew, and flower powdery mildew.
The invention has the advantages that
The invention combines the active component A and the active component B according to different proportions, effectively improves the disease control effect, has obvious synergistic effect, delays the generation of drug resistance of pathogenic bacteria and prolongs the service life of the medicament.
Detailed Description
The synergistic effect of the compositions of the present invention on harmful fungi is further illustrated by the following examples, but the invention is by no means limited thereto. Wherein the active components are the active component A and the nucleic acid metabolism bactericide B in the fungicidal composition; and the preparation of the active component A is described in patent CN 102336744B.
The test method and the evaluation method are as follows:
the active samples to be tested are respectively an active component A, an active component B, and a composition of the active component A and the active component B.
The active component A is an active component A1 or an active component A2, and the active component A2 is a salt formed by the compound A1 and sulfuric acid;
the active component A is a compound A1 shown in a general formula I (taking the compound as an example):
in the general formula:
q is selected from Q2 shown below:
w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; n=0; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O); namely, the compound A1.
The active component B is selected from metalaxyl-B1, metalaxyl-B7 and bupirimate B5 of nucleic acid metabolism inhibitor bactericides.
The composition to be tested is composed of an active component A1 and an active component B which are respectively selected from metalaxyl-M B1, metalaxyl-M B7 and bupirimate B5 of nucleic acid metabolism inhibitor bactericides; or the active component A2 and the active component B are selected from metalaxyl-M B1, benalaxyl-M B7 and bupirimate B5 of nucleic acid metabolism inhibitor bactericides.
The specific mode is as follows:
dissolving the above active components or compositions with acetone or water (the volume ratio of acetone to spray amount is equal to or less than 0.05), diluting with water containing 0.1% Tween 80, and preparing into desired concentration solution to be tested, and mixing the solutions to be tested according to a set proportion. And spraying the liquid to be detected on the disease host plants on a crop sprayer, and inoculating the disease after 24 hours. According to the disease characteristics, the disease plants which need to be subjected to temperature control and moisture preservation culture are inoculated and then placed in a climatic chamber for culture, and after the infection of the disease is completed, the plants are transferred into a greenhouse for culture. After the control is sufficiently ill, the percentage of leaf area of the pathogen-infected crop is determined and calculated using the Abbot formula to obtain the observed efficacy (W):
W＝(1-α/β)×100
wherein:
alpha: percent fungal infestation of the treated crop;
beta: percent fungal infestation of untreated (control) crops;
efficacy of "0" means that the level of infestation of the treated crop is the same as the level of infestation of the untreated control crop; efficacy of "100" means that the treated crop was not infested.
The expected efficacy (calculated efficacy) of the composition was determined using the Colby formula (see r.s. Colby, weeds, 1967, 15, 20-22) and compared to the observed efficacy.
E＝X+Y–XY/100
Wherein:
e: the expected efficacy (calculated efficacy in the tables below) when using the compositions of active components a and B at concentrations a and B, expressed as% of untreated control;
x: efficacy of active ingredient a at a concentration a was used, expressed as% of untreated control;
y: the efficacy of active ingredient B at a concentration B was used, expressed as% of untreated control.
When the observed efficacy value is greater than the calculated efficacy value, the composition is indicated to have a synergistic effect; when the observed efficacy value is equal to the calculated efficacy value, the composition is indicated to be additive; when the observed efficacy value is less than the calculated efficacy value, the composition is indicated to be antagonistic.
Example 1 test for controlling cucumber downy mildew
The cucumber seedlings in the two-leaf stage of the potted plant with the variety 'Xintaimi thorns' are subjected to spray treatment by using water solutions of each active component or composition (the concentration of the active components is shown in the table below), inoculated with a cucumber downy mildew sporangium suspension after 24 hours, cultured in a climatic chamber, transferred into a greenhouse for culture after the infection of diseases is completed, and the development degree of pathogen infection on the leaves is measured after 7 days.
The activity data of each individual active ingredient and the composition of the invention for controlling cucumber downy mildew are shown in tables 1 and 2.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 1 Activity of the individual active ingredients
TABLE 2 Activity of the compositions of the invention
Example 2 test for controlling tomato late blight
Potted tomato seedlings of the variety L-402 are sprayed with an aqueous solution of each active component or composition (the concentrations of the active components are shown in the following table), inoculated with a sporangium suspension of late blight after 24 hours, and cultivated in a climatic chamber, after the disease is infected, transferred into a greenhouse for cultivation, and the extent of pathogen infection on the leaves is measured after 3 days.
The activity data of each individual active ingredient and the compositions of the present invention for controlling tomato late blight are shown in tables 3 and 4.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 3 Activity of the individual active ingredients
TABLE 4 Activity of the compositions of the invention
Example 3 test for controlling pepper epidemic disease
Potted pepper seedlings of the variety "Lantern peppers" were sprayed with aqueous solutions of the respective active ingredients or compositions (the concentrations of the active ingredients are as indicated in the following table), inoculated with a sporangium suspension after 24 hours, and cultivated in a climatic chamber, after the disease was completed, transferred into a greenhouse for cultivation, and after 5 days the extent of pathogen infestation on the leaves was determined.
The data of the activity of each individual active ingredient and the composition of the present invention for controlling pepper epidemic disease are shown in tables 5 and 6.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 5 Activity of the individual active ingredients
TABLE 6 Activity of the compositions of the invention
Example 4 test for controlling powdery mildew of Capsici fructus
Pepper seedlings of the variety "Hangzhou pepper No. one" were sprayed with aqueous solutions of the respective active ingredients or compositions (concentrations as described in the following table), 24 hours later, pepper powdery mildew spore suspensions were inoculated on pepper leaves, cultured in a greenhouse, and after 15 days, the extent of development of pathogen infection on the leaves was determined.
The activity data of each individual active ingredient and the composition of the invention for controlling powdery mildew of capsicum are shown in tables 7 and 8.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 7 Activity of the individual active ingredients
TABLE 8 Activity of the compositions of the invention
Example 5 test for controlling powdery mildew of cucumber
The two-leaf stage cucumber seedlings of the variety Xintaimi thorns are sprayed with an aqueous solution (the concentration is shown in the table below) of each active component or composition, after 24 hours, the cucumber powdery mildew spore suspension is inoculated on cucumber leaves, the cucumber leaves are cultured in a greenhouse, and after 15 days, the development degree of germ infection on the leaves is measured.
The activity data of each individual active ingredient and the composition of the invention for preventing and treating powdery mildew of cucumber are shown in table 9 and table 10.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 9 Activity of the individual active ingredients
TABLE 10 Activity of the compositions of the invention
Example 6 test for controlling powdery mildew of eggplant
Potted eggplant seedlings of the variety Liaoeggplant No. 1 are sprayed with an aqueous solution (the concentrations of the active components or compositions are shown in the following table), after 24 hours, eggplant powdery mildew spore suspensions are inoculated on eggplant leaves, the eggplant seedlings are cultivated in a greenhouse, and after 15 days, the development degree of germ infection on the leaves is measured.
The data of the activity of each individual active component and the composition for preventing and treating powdery mildew of eggplant are shown in Table 11 and Table 12.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 11 Activity of the individual active ingredients
TABLE 12 Activity of the compositions of the invention
Claims (7)
1. A fungicidal composition comprising a substituted triazolinone ether compound, characterized in that: the composition comprises A, B two active components, wherein the weight ratio of the active component A to the active component B is 1:99-99:1;
the active component A is a compound shown in a general formula I or a salt thereof;
in the general formula:
q is selected from Q1 or Q2 as shown below:
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen, halogen, cyano, nitro, CH 2 CN, C1-C6 alkyl, halogenated C1-C6 alkyl or C3-C6 cycloalkyl, R 3 Selected from hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl;
when Q is selected from Q2: r is R 2 Selected from halogen, C1-C6 alkyl, halogenated C1-C6 alkyl or C3-C6 cycloalkyl, R 3 Selected from C1-C6 alkyl or halogenated C1-C6 alkyl;
R 4 selected from halogen, cyano, nitro, hydroxy, C1-C4 alkyl, halo C1-C3 alkyl, C1-C3 alkoxy, halo C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfonyl, phenyl or phenoxy, unsubstituted or substituted with 1 to 5 groups independently selected from chloro, bromo, fluoro, nitro, cyano, trifluoromethyl, C1-C3 alkyl, C1-C3 alkoxy or halo C1-C3 alkoxy; n=0-5;
R 5 、R 6 and may be the same or different and are each selected from hydrogen, halogen, nitro, cyano, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, unsubstituted or substituted with 1 to 5 groups independently selected fromPhenyl, pyridyl, furyl, thienyl or thiazolyl substituted by radicals, the radicals being halogen, cyano, nitro, CO 2 (C1-C4 alkyl), C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio or C1-C6 alkylsulfonyl;
y is selected from halogen, OR 7 、SR 7 、SOR 7 、SO 2 R 7 Or NHR 7 The method comprises the steps of carrying out a first treatment on the surface of the Wherein R is 7 Selected from hydrogen or C1-C4 alkyl;
the active component B is selected from one or more of metalaxyl B1, metalaxyl B2, bupirimate B3, pyriminostrobin B4, pyriminostrobin B5, benalaxyl B6, benalaxyl B7, furalaxyl B8, furalamide B9, oxadixyl B10, xin Saitong B11 and quinidone B12 serving as nucleic acid metabolism inhibitor bactericides.
2. A fungicidal composition according to claim 1, characterized in that: the active component A is selected from compounds shown in a general formula I or salts thereof;
in the general formula:
q is selected from Q1 or Q2 as shown below:
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen, fluorine, chlorine, bromine or C1-C4 alkyl, R 3 Selected from hydrogen or C1-C6 alkyl;
when Q is selected from Q2: r is R 2 Selected from C1-C4 alkyl, R 3 Selected from C1-C6 alkyl;
R 4 selected from halogen, cyano, nitro, C1-C4 alkyl, halogenated C1-C3 alkyl, C1-C3 alkoxy, halogenated C1-C3 alkoxy or C1-C3 alkylsulfonyl;
n＝0-3；
R 5 、R 6 which may be the same or different, are each selected from hydrogen, chlorine, bromine, fluorine, nitro, cyano, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy or halogenated C1-C4 alkoxy;
y is selected from Cl, OR 7 Or SR (S.J) 7 The method comprises the steps of carrying out a first treatment on the surface of the Wherein R is 7 Selected from C1-C4 alkyl;
the salt of the compound shown in the general formula I is the salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid and fumaric acid;
the active component B is selected from one or more of metalaxyl B1, bupirimate B3, pyriminostrobin B4, pyriminostrobin B5, benalaxyl B6, metalaxyl B7, furalaxyl B8, furalamide B9, oxadixyl B10 and quinidone B12 serving as nucleic acid metabolism inhibitor bactericides;
A. the weight ratio of the two active components is 1:50-50:1.
3. A fungicidal composition according to claim 2, characterized in that: the active component A is selected from compounds shown in a general formula I or salts thereof;
in the general formula:
q is selected from Q1 or Q2;
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen or methyl, R 3 Selected from hydrogen, methyl or ethyl;
when Q is selected from Q2: r is R 2 Selected from methyl, R 3 Selected from methyl;
R 4 selected from halogen, cyano, nitro, methyl, ethyl, isopropyl, t-butyl, CF 3 、CH 3 O or CF 3 O；
n＝0-3；
R 5 、R 6 May be the same or different and are each selected from hydrogen, chlorine, bromine, fluorine or C1-C4 alkyl;
y is selected from Cl, CH 3 O or CH 3 S；
The salt of the compound shown in the general formula I is the salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid and benzoic acid;
the active component B is selected from one or more of metalaxyl B1, pyriminostrobin B4, bupirimate B5, benalaxyl B6, metalaxyl B7, furalamide B9, oxadixyl B10 and quinidone B12 serving as nucleic acid metabolism inhibitor bactericides;
the weight ratio of the A, B active components is 1:20-20:1.
4. A fungicidal composition according to claim 2, characterized in that: the active component A is selected from compounds shown in a general formula I or salts thereof;
in the general formula:
q is selected from Q2;
w is selected from O;
R 1 selected from methyl;
R 2 selected from methyl, R 3 Selected from methyl;
R 4 selected from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, CF 3 、CH 3 O or CF 3 O；
n=0, 1, 2 or 3;
R 5 、R 6 may be the same or different and are each selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl or isopropyl;
y is selected from Cl or CH 3 O；
The salt of the compound shown in the general formula I is a salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid and acetic acid;
the active component B is selected from one or more of metalaxyl B1, pyriminobac-methyl B4, bupirimate B5, metalaxyl B7, oxadixyl B10 and quinidone B12 serving as nucleic acid metabolism inhibitor bactericides;
the weight ratio of the A, B active components is 1:10-10:1.
5. The fungicidal composition of claim 4, wherein: the active component A is selected from compounds shown in a general formula I or salts thereof;
in the general formula:
q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; n=0; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O)；
Or Q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; r is R 4 Selected from fluorine; n=1; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O)；
Or Q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; r is R 4 Selected from chlorine; n=1; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O)；
The salt of the compound shown in the general formula I is a salt formed by the compound shown in the general formula I, hydrochloric acid and sulfuric acid;
the active component B is selected from one or more of metalaxyl-M B1, bupirimate B5 and metalaxyl-M B7 serving as nucleic acid metabolism inhibitor bactericides;
the weight ratio of the A, B active components is 1:4-4:1.
6. Use of a fungicidal composition characterized in that: the fungicidal composition is used for preparing medicines for preventing and treating plant pathogenic fungi diseases.
7. The use according to claim 6, characterized in that: the plant pathogenic fungus disease is plant downy mildew, late blight, epidemic disease, black shank, damping-off or powdery mildew.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111612888.0A CN116349683A (en) | 2021-12-27 | 2021-12-27 | Fungicidal composition containing substituted triazolinone ether compound and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111612888.0A CN116349683A (en) | 2021-12-27 | 2021-12-27 | Fungicidal composition containing substituted triazolinone ether compound and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116349683A true CN116349683A (en) | 2023-06-30 |
Family
ID=86914440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111612888.0A Withdrawn CN116349683A (en) | 2021-12-27 | 2021-12-27 | Fungicidal composition containing substituted triazolinone ether compound and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116349683A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102336744A (en) * | 2010-07-20 | 2012-02-01 | 中国中化股份有限公司 | Substituted triazoline ether ketone class compound and application thereof as bactericide as well as insecticide and acaricide |
| CN102336742A (en) * | 2010-07-20 | 2012-02-01 | 中国中化股份有限公司 | Substituted triazolinone ether compounds and application thereof |
| CN102336743A (en) * | 2010-07-20 | 2012-02-01 | 中国中化股份有限公司 | Triazoline ketone ether-substituted compound and application thereof |
| CN111316987A (en) * | 2018-12-14 | 2020-06-23 | 沈阳中化农药化工研发有限公司 | Fungicidal composition and application thereof |
-
2021
- 2021-12-27 CN CN202111612888.0A patent/CN116349683A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102336744A (en) * | 2010-07-20 | 2012-02-01 | 中国中化股份有限公司 | Substituted triazoline ether ketone class compound and application thereof as bactericide as well as insecticide and acaricide |
| CN102336742A (en) * | 2010-07-20 | 2012-02-01 | 中国中化股份有限公司 | Substituted triazolinone ether compounds and application thereof |
| CN102336743A (en) * | 2010-07-20 | 2012-02-01 | 中国中化股份有限公司 | Triazoline ketone ether-substituted compound and application thereof |
| CN111316987A (en) * | 2018-12-14 | 2020-06-23 | 沈阳中化农药化工研发有限公司 | Fungicidal composition and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111316987B (en) | Fungicidal composition and application thereof | |
| CN109805017B (en) | Fungicidal composition and application thereof | |
| SK284549B6 (en) | Fungicidal two- or three-component composition based on metalaxyl, method of controlling and preventing Oomycetes infestation | |
| CN111316990B (en) | Fungicidal compositions and their use | |
| CN108260593B (en) | Bactericidal composition | |
| EP1419693B1 (en) | Composition for controlling plant pathogenic bacterium and method of controlling plant pathogenic bacterium | |
| CN111316991B (en) | Fungicidal compositions and uses | |
| CN111316992B (en) | Fungicidal composition and application thereof | |
| CN116349683A (en) | Fungicidal composition containing substituted triazolinone ether compound and application thereof | |
| CN103651492A (en) | Fungicidal composition containing iprodione and triclopyricarb and application thereof | |
| CN105532696B (en) | Fungicidal composition and its application | |
| CN116349682A (en) | Fungicidal composition containing cell wall synthesis inhibitor bactericides and application thereof | |
| WO2021004195A1 (en) | Fungicidal and bactericidal composition and application | |
| CN116349681A (en) | Fungicidal composition and application thereof | |
| CN116349685A (en) | Fungicidal composition containing cytoskeletal and kinesin inhibitor bactericides and application thereof | |
| CN114532346B (en) | Fungicidal and bacterial composition and application thereof | |
| CN116349686A (en) | Fungicidal composition containing substituted triazolinone ether compound and application thereof | |
| CN112189663B (en) | Fungicidal and bacterial composition and application | |
| CN112189669B (en) | Fungicidal and bacterial compositions and uses | |
| CN112189660B (en) | Fungicidal and bacterial compositions and uses thereof | |
| CN116349684A (en) | Fungicidal composition containing sterol biosynthesis inhibitor bactericide and application thereof | |
| CN112189668B (en) | Fungicidal and bacterial composition and application | |
| CN112189665B (en) | Fungicidal bacterium composition and application | |
| CN112189661B (en) | Fungicidal and bacterial compositions and uses | |
| CN112189662B (en) | Fungicidal and bacterial compositions and uses thereof |
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 | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20230630 |