CN1923819A - compound containing aromatic ether and ditriazole and use thereof - Google Patents
compound containing aromatic ether and ditriazole and use thereof Download PDFInfo
- Publication number
- CN1923819A CN1923819A CN200610140836.7A CN200610140836A CN1923819A CN 1923819 A CN1923819 A CN 1923819A CN 200610140836 A CN200610140836 A CN 200610140836A CN 1923819 A CN1923819 A CN 1923819A
- Authority
- CN
- China
- Prior art keywords
- acid
- aryl oxide
- triazole compounds
- agroforestry
- fungal disease
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title abstract description 14
- 150000008378 aryl ethers Chemical class 0.000 title abstract 2
- -1 C1-4 Chemical group 0.000 claims abstract description 53
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 11
- 241000233866 Fungi Species 0.000 claims abstract description 10
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 229910052736 halogen Chemical group 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 208000031888 Mycoses Diseases 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 239000011833 salt mixture Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 241000235349 Ascomycota Species 0.000 claims description 4
- 241000221198 Basidiomycota Species 0.000 claims description 4
- 241000082085 Verticillium <Phyllachorales> Species 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- 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 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 150000003852 triazoles Chemical class 0.000 description 12
- 239000005760 Difenoconazole Substances 0.000 description 9
- 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 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003899 bactericide agent Substances 0.000 description 7
- 230000000855 fungicidal effect Effects 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 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 5
- 239000005839 Tebuconazole Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- 241000223218 Fusarium Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000000645 desinfectant Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000000452 restraining effect Effects 0.000 description 3
- KVKFSLYUIUDSOI-UHFFFAOYSA-N 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol Chemical compound C1=NC=NN1CC(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)(O)CN1C=NC=N1 KVKFSLYUIUDSOI-UHFFFAOYSA-N 0.000 description 2
- 241000193738 Bacillus anthracis Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000016623 Fragaria vesca Nutrition 0.000 description 2
- 240000009088 Fragaria x ananassa Species 0.000 description 2
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 2
- 241000223195 Fusarium graminearum Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 244000081841 Malus domestica Species 0.000 description 2
- 244000070406 Malus silvestris Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241000233629 Phytophthora parasitica Species 0.000 description 2
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 244000000004 fungal plant pathogen Species 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 235000010603 pastilles Nutrition 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 244000241235 Citrullus lanatus Species 0.000 description 1
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 1
- 229940126639 Compound 33 Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- NZFGOIAABVIWFM-UHFFFAOYSA-N FC1=C(C=CC(=C1)OC1=CC=C(C=C1)F)C(CN1N=CN=C1)(O)CN1N=CN=C1 Chemical compound FC1=C(C=CC(=C1)OC1=CC=C(C=C1)F)C(CN1N=CN=C1)(O)CN1N=CN=C1 NZFGOIAABVIWFM-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000233732 Fusarium verticillioides Species 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241001512566 Valsa mali Species 0.000 description 1
- 241001123668 Verticillium dahliae Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- OQTFFGSVBUKNQJ-UHFFFAOYSA-N [S].[O].C[NH+](C)C.I(=O)(=O)[O-] Chemical compound [S].[O].C[NH+](C)C.I(=O)(=O)[O-] OQTFFGSVBUKNQJ-UHFFFAOYSA-N 0.000 description 1
- 244000193174 agave Species 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000005013 aryl ether group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000010534 mechanism of action Effects 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
- 238000000034 method Methods 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000009711 regulatory function Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a diribavirin compound with aromatic ether and application, which possesses structural formula as formula (I) or antimer of formula (I), wherein R1, R2, R3, R4, R5, R6 is hydrogen, C1-4, trifluoromethyl, methoxyl, nitro group or halogen; the C1-4 alkyl is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, parabutyl or tert-butyl group; the atom is F, Cl, Br or I; the compound displays strong fungi inhibiting activity, which can prepare fungi inhibitor.
Description
Technical field
The present invention relates to agricultural and use the sterilant field, particularly a kind ofly contain the two triazole compounds of aryl oxide and acid salt thereof, metal-salt mixture, and the preparation method and as agricultural with sterilant in the purposes of preventing and treating on the agroforestry fungal disease.
Background technology
Endangering animals and plants and making the morbific harmful organism of animals and plants mainly is fungi, bacterium and virus.For plant, the main disease of plant is a fungal disease.The commercial sterilizing disease-preventing medicament overwhelming majority is a mycocide, and bactericide is then very few, and the diseases prevention toxic agent is very few for number.One of factor is exactly that fungal disease has general property, and harm that causes and loss are also maximum.In numerous fungal disease control agent, triazole bactericidal agent is typical fungicidal type.Over nearly 30 years, triazole bactericidal agent is efficient with it, low toxicity, wide spectrum and enjoy favor, and moreover, most triazole bactericidal agents have the plant biological regulatory function simultaneously.Triazole bactericidal agent is interior suction therapeutic type sterilant but then, and mechanism of action and action site are single, long-term frequent use, and disease has produced more serious resistance, and many kinds are because resistance problem has lost original high efficiency.As triazolone control powdery mildew of strawberry, the few preventive effect of consumption is low, and consumption greatly then easily produces poisoning, suppresses the strawberry growth.Thereby the triazole bactericidal agent of development of new just becomes the task of top priority.
English Patent GB2078719A discloses the two triazole compounds with fungicidal activity, but its substituting group of the disclosed compound of this patent does not comprise aryl ether group.The invention provides the new two triazole class sterilant of aryl oxide that contain, the part of compounds bacteriostatic activity is suitable with commercialization triazole bactericidal agent tebuconazole, Difenoconazole, has good commercialization prospect.
Summary of the invention
Technical problem to be solved by this invention be to provide a kind of have a high biological activity contain the two triazole compounds of aryl oxide and acid salt thereof, metal-salt mixture as agricultural with sterilant.
Another technical problem to be solved by this invention is to provide a kind of above-mentioned two triazole compounds of aryl oxide and acid salt thereof, metal-salt mixture of containing in the application that prevents and treats on the agroforestry fungal disease, these diseases are fungus-caused by a plurality of genus that are under the jurisdiction of Ascomycota, Basidiomycota, imperfect fungi door mostly, as Staphlosporonites, interlink spore genus, black star spore genus, Verticillium, reaping hook genus, spherical shell spore genus etc.For solving the problems of the technologies described above, the invention provides a kind of two triazole compounds of aryl oxide that contain, have following structural formula (I) or described structural formula (I) acceptable enantiomorph on agricultural pharmacology:
Wherein, R
1, R
2, R
3, R
4, R
5, R
6Be hydrogen, C
1～4Alkyl, trifluoromethyl, methoxyl group, nitro or halogen;
Described C
1～4Alkyl is methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl or the tertiary butyl;
Described halogen atom is fluorine, chlorine, bromine or iodine.
Described R
1, R
2, R
3, R
4, R
5, R
6Substituting group can be the same or different.
The acid of described acid salt can be in hydrochloric acid, Hydrogen bromide, nitric acid, sulfuric acid, phosphoric acid, hydroiodic acid HI, hydrofluoric acid, perchloric acid, tosic acid, methylsulfonic acid, acetate, citric acid, tartrate, oxysuccinic acid, oxalic acid, fumaric acid or the phthalic acid one or more.
The metal-salt mixture of the two triazole compounds of described aryl oxide is characterized in that having following structural formula (II):
Wherein, R
1, R
2, R
3, R
4, R
5, R
6Be hydrogen, C
1～4Alkyl, trifluoromethyl, methoxyl group, nitro or halogen;
Described C
1～4Alkyl is methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl or the tertiary butyl;
Described halogen atom is fluorine, chlorine, bromine or iodine;
Described M is the period of element Table II
A, IV
A, I
B, II
B, VI
B, VII
BOr the positively charged ion of VIII family;
Described Y is the negatively charged ion of neutralizing cation M electric charge.
Described contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
Described contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease, described agroforestry fungal disease is fungus-caused by the one or more genus that are under the jurisdiction of Ascomycota, Basidiomycota, imperfect fungi door.
Described contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease, described agroforestry fungal disease be by Staphlosporonites, interlink spore genus, black star spore genus, Verticillium, reaping hook belongs to or one or more of spherical shell spore genus are fungus-caused.
The described acid salt that contains the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
The metal-salt mixture of the two triazole compounds of described aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
Compound provided by the invention not only has higher biological activity, and low with the analogous products comparative cost of production, is the disinfectant use in agriculture new variety that application prospect is arranged very much.
Embodiment
The present invention contains the two triazole class fungicide compounds (I) of aryl oxide and agricultural goes up acceptable acid salt and metal-salt mixture, and general formula is:
Wherein, R
1, R
2, R
3, R
4, R
5, R
6Be H, C
1～4Alkyl, trifluoromethyl, methoxyl group, nitro or halogen, R
1, R
2, R
3, R
4, R
5, R
6Can be identical or different;
Above-mentioned C
1～4Alkyl is methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl, the tertiary butyl; Above-mentioned halogen atom is fluorine, chlorine, bromine, iodine.
In table 1 triazole class compounds of the present invention
The chemical structure of group for example
| Routine number | R 1 | R 2 | R 3 | R 4 | R 5 | R 6 |
| 1 | H | H | H | H | H | H |
| 2 | H | H | Cl | H | H | 6-Cl |
| 3 | Cl | H | Cl | H | H | H |
| 4 | H | H | Cl | H | H | H |
| 5 | H | Cl | H | 5-Cl | H | H |
| 6 | H | Cl | H | 6-Cl | H | H |
| 7 | H | Cl | H | H | H | H |
| 8 | H | Br | H | H | H | H |
| 9 | H | H | CH 3 | H | H | H |
| 10 | CH 3 | H | CH 3 | H | H | H |
| 11 | F | H | H | H | H | H |
| 12 | H | F | H | H | H | H |
| 13 | H | H | F | H | H | H |
| 14 | Br | H | H | H | H | H |
| 15 | H | H | Br | H | H | H |
| 16 | C 2H 5 | H | H | H | H | H |
| 17 | H | H | C 4H 9-t | H | H | H |
| 18 | OCH 3 | H | H | H | H | H |
| 19 | H | H | NO 2 | H | H | H |
| 20 | CF 3 | H | H | H | H | H |
| 21 | H | H | CF 3 | H | H | H |
| 22 | Br | H | Br | H | H | H |
| 23 | Br | H | Cl | H | H | H |
| 24 | Cl | H | Br | H | H | H |
| 25 | H | Cl | Cl | 6-Cl | H | H |
| 26 | CH 3 | H | Cl | H | H | H |
| 27 | NO 2 | H | CF 3 | H | H | H |
| 28 | NO 2 | H | NO 2 | 6-CF 3 | H | H |
| 29 | Cl | Cl | H | H | H | H |
| 30 | CH 3 | H | H | H | 2-CH 3 | H |
| 31 | H | H | Cl | H | 2-CH 3 | H |
| 32 | Cl | H | CF 3 | H | H | H |
| 33 | Cl | H | CF 3 | H | H | 6-Cl |
| 34 | H | H | Cl | H | 2-CH 3 | H |
| 35 | H | F | H | H | 2-CH 3 | H |
| 36 | CH 3 | H | H | H | 2-CH 3 | H |
| 37 | H | H | OCH 3 | H | 2-CH 3 | H |
| 38 | H | H | F | H | 2-CH 3 | H |
| 39 | OCH 3 | H | H | H | 2-Cl | H |
| 40 | H | H | F | H | 2-OCH 3 | H |
| 41 | H | H | Cl | H | 3-Cl | H |
| 42 | H | H | Cl | H | 2-C 2H 5 | H |
| 43 | H | H | H | H | 2-CH 3 | H |
| 44 | H | H | H | H | 2-Cl | H |
| 45 | H | H | H | H | 3-CH 3 | H |
| 46 | H | H | H | H | 2-CH 3 | 5-CH 3 |
| 47 | H | H | H | H | 2-C 2H 5 | H |
| 48 | H | H | CF 3 | H | 3-Cl | H |
| 49 | H | H | F | H | H | 6-Cl |
| 50 | H | H | F | H | H | 6-F |
Title compound (I) can be directly with the preparation disinfectant use in agriculture, also can the agriculture form that goes up the acceptable acid salt prepare disinfectant use in agriculture, acid comprises hydrochloric acid, Hydrogen bromide, nitric acid, sulfuric acid, phosphoric acid, hydroiodic acid HI, hydrofluoric acid, perchloric acid, tosic acid, methylsulfonic acid, acetate, citric acid, tartrate, oxysuccinic acid, oxalic acid, fumaric acid and phthalic acid.
Another embodiment of the present invention is the metal-salt mixture (II) of formula (I):
R wherein
1, R
2, R
3, R
4, R
5And R
6Definition cotype (I), M is for being selected from the period of element Table II
A, IV
A, I
B, II
B, VI
B, VII
BWith the positively charged ion of VIII family, Y is used for the negatively charged ion of the electric charge of neutralizing cation M for selection.
The typical positively charged ion of the present invention is magnesium, copper, nickel, zinc, iron, cobalt, calcium, tin, chromium, mercury, barium etc.
The typical negatively charged ion of the present invention is chlorine, bromine, iodine, fluorine, thiocyanate ion, sulfate radical, bisulfate ion, perchlorate, nitrate radical, nitrite anions, phosphate radical, carbonate, bicarbonate radical, oxalate, tartrate anion, malate, horse Lay acid group, fumaric acid radical, tosic acid root, methanesulfonate etc.
Having of greater activity arranged among the present invention:
Compound 2 α-(2-chloro-4-(4-chlorophenoxy) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2,4-triazol-1-yl ethanol
Compound 33 α-(2-chloro-4-(2-chloro-4-4-trifluoromethylphenopendant) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2,4-triazol-1-yl ethanol
Compound 32 α-(4-(2-chloro-4-4-trifluoromethylphenopendant) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2,4-triazol-1-yl ethanol
Compound 50 α-(2-fluoro-4-(4-fluorophenoxy) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2,4-triazol-1-yl ethanol
Compound with structural formula (I) of the present invention can be made as follows:
R in the formula
1, R
2, R
3, R
4, R
5And R
6Implication is same as above.
Reaction by ether ketone be raw material through bromo, azanylization, epoxidation is last reacts open loop with triazole and get target compound.Concrete reaction conditions is as follows:
Example I: α-(2-chloro-4-(4-chlorophenoxy) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2, the preparation of 4-triazol-1-yl alcoholic acid
2-bromo-1-(2-chloro-4-(4-chlorophenoxy) phenyl) ethyl ketone
In the 500mL four-necked bottle, add 280g (1.0mol) 2-chloro-4-(4-chlorophenoxy) methyl phenyl ketone, 200mL hexanaphthene, stirring at room, drip 192g (1.2mol) bromine, add 2～3 earlier, solution takes on a red color, wait redness to take off after, more remaining bromine is dripped into, the control rate of addition, about 3h drips off.Keep temperature of reaction and continue to stir 2h to color fade, stopped reaction.Reaction solution is poured in the 500mL separating funnel, washed with water, branch vibration layer is washed to organic phase repeatedly and is neutral, tells organic phase, spends the night with anhydrous magnesium sulfate drying.Elimination sal epsom removes hexanaphthene under reduced pressure, gets faint yellow solid, and recrystallization gets white crystal 335.2g, yield 93.1%.Fusing point: 50～51 ℃.
The preparation of 2-(1H-1,2,4-triazol-1-yl)-1-(2-chloro-4-(4-chlorophenoxy) phenyl) ethyl ketone
In the 500mL four-necked bottle, add 180g (0.5mol) 2-bromo-1-(2-chloro-4-(4-chlorophenoxy) phenyl) ethyl ketone, 51.8g (0.75mol) triazole, 103.5g (0.75mol) potassium carbonate powder and 200mL ethyl acetate respectively, heating reflux reaction 6h, filter, filtrate subtracts steaming, get light yellow solid, recrystallization gets white solid 117.2g, yield 67.3%, fusing point: 151～154 ℃.
1-[2-(2-chloro-4-(4-chlorophenoxy) phenyl)-2, the 3-epoxypropyl]-1H-1,2, the preparation of 4-triazole mesylate
Get 2-(1H-1,2, the 4-triazol-1-yl)-and 1-(2-chloro-4-(4-chlorophenoxy) phenyl) ethyl ketone 34.8g (0.1mol), iodate trimethylammonium oxygen sulphur 26.4g (0.12mol), trimethylammonium hexadecyl brometo de amonio 0.3g and toluene 100mL put into the 250mL three-necked bottle, be warming up to 60 ℃, stir the sodium hydroxide solution 80mL of dropping 20% down, 2h drips off, and is incubated 60 ℃ and continues to stir 3 hours, isolate toluene layer, be concentrated into 25mL.Debris adds the dilution of 15mL ethyl acetate, 0 ℃ drips down and is dissolved with the ethyl acetate solution 5mL of 9.6g methylsulfonic acid, adds the ethyl acetate dilution again, 0 ℃ was stirred one hour down, get faint yellow precipitation 1-[2-(2-chloro-4-(4-chlorophenoxy) phenyl)-2, the 3-epoxypropyl]-1H-1,2,4-triazole mesylate, the crude product recrystallization is got faint yellow solid 32.2g, yield 70.2%, fusing point: 130～134 ℃.
α-(2-chloro-4-(4-chlorophenoxy) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2, the preparation of 4-triazol-1-yl alcoholic acid
In 50mL single port flask, add 1-[2-(2-chloro-4-(4-chlorophenoxy) phenyl)-2, the 3-epoxypropyl]-1H-1,2,4-triazole mesylate 4.6g (0.01mol), triazole 0.8g (0.012mol), potassium carbonate powder 1.4g (0.01mol) and N, dinethylformamide 20mL, back flow reaction 6h pours reaction solution in the water into, and the adularescent solid is separated out, suction filtration gets α-(2-chloro-4-(4-chlorophenoxy) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2,4-triazol-1-yl ethanol crude product, recrystallization gets white crystal 1.8g, yield 41.5%, 141～143 ℃ of fusing points.
1H NMR：8.12(2H，s，2triazole C5-H)，7.89(2H，s，2triazoleC3-H)，6.74-7.57(7H，m，Ar-H)，5.50(1H，s，OH)，5.08-5.10(2H，d，CH2)，4.59-4.61(2H，d，CH2).
All the other target compounds are synthesis material with different replacement aryl ether ketones, and are listed as table 1, repeat the step in the example I, just can synthesize the required two triazole compounds of aryl oxide that contain.
Synthetic of the present invention contains the two triazole compounds of aryl oxide and has the effect of the fungi of inhibition, sets forth its living experimental result of surveying below.
Experimental technique: adopt the Plating that exsomatizes
Materials and methods
(1) test strain
Agriculture frequently seen plants fungal disease in the table 2 is selected in this experiment for use, these diseases are fungus-caused by a plurality of genus that are under the jurisdiction of Ascomycota, Basidiomycota, imperfect fungi door, for example Staphlosporonites, interlink spore genus, black star spore genus, Verticillium, reaping hook belong to, the spherical shell spore belongs to or the like, have represented the panoramic plant pathogenic fungi of nature.
(2) test method
Reagent agent is diluted to desired concn respectively by effective constituent, under aseptic condition, respectively draws the 1mL soup and inject in the culture dish, add the 9mL substratum more respectively, make 5 μ g/mL pastille flat boards after shaking up, do blank with the flat board that adds the 1mL aqua sterilisa.Punch tool with diameter 4mm cuts the bacterium dish along the mycelia outer rim, moves on the pastille flat board every processing triplicate.Culture dish is placed on cultivation in 24 ± 1 ℃ of constant incubators.The 72h " Invest, Then Investigate " is respectively handled bacterium dish expansion diameter, averages, and relatively calculates relative bacteriostasis rate with blank.
Experimental result
The part of compounds bacteriostatic experiment the results are shown in Table 2, table 3:
Table 2: fungicidal activity (5 μ g/mL), %
| The fungi title | Fungicidal activity (5 μ g/mL), % | ||
| Difenoconazole | Tebuconazole | Compound 2 | |
| Sugar beet leaf spot bacteria | 100.0 | 100.0 | 100.0 |
| Fusarium moniliforme | 100.0 | 100.0 | 100.0 |
| Cucumber fusarium axysporum | 80.9 | 99.0 | 80.9 |
| Peanut Cercospora bacteria | 100.0 | 100.0 | 100.0 |
| Asparagus stem wilt bacteria | 100.0 | 100.0 | 100.0 |
| Tomato early blight bacterium | 84.2 | 84.2 | 84.2 |
| Fusarium graminearum | 100.0 | 100.0 | 100.0 |
| The ring rot of apple bacterium | 94.5 | 91.0 | 91.0 |
| The rice green smut bacterium | 100.0 | 100.0 | 100.0 |
| Dosporium cucumerinumand its | 94.5 | 91.0 | 91.0 |
| Botrytis cinerea pers | 99.0 | 99.0 | 99.0 |
| Sclerotinia sclerotiorum | 99.0 | 99.0 | 99.0 |
| Apple zonate spot bacterium | 99.0 | 99.0 | 99.0 |
| Valsa mali | 99.0 | 99.0 | 99.0 |
| Glorosprium musarum Cookeet Mass | 100.0 | 100.0 | 100.0 |
| The brown edge germ of banana | 86.5 | 86.5 | 83.8 |
| Watermelon anthrax bacteria | 99.0 | 88.5 | 99.0 |
| Apple anthrax bacteria | 100.0 | 99.0 | 100.0 |
| Cucumber anthracnose | 100.0 | 100.0 | 100.0 |
| The pears alternaria | 99.0 | 99.0 | 99.0 |
| The root rotof flax bacterium | 99.0 | 99.0 | 99.0 |
| The miliary damping-off germ | 99.0 | 95.0 | 99.0 |
| Cereal silk nuclear germ | 99.0 | 99.0 | 99.0 |
| Cotton-wilt fusarium | 76.2 | 90.5 | 80.9 |
| Verticillium dahliae | 92.3 | 92.3 | 92.3 |
| Southern corn leaf blight | 99.0 | 99.0 | 99.0 |
Table 3: fungicidal activity (1 μ g/mL), %
| The fungi title | Fungicidal activity (1 μ g/mL), % | ||
| Difenoconazole | Tebuconazole | Compound 2 | |
| Fusarium graminearum | 73.9 | 86.9 | 82.6 |
| Tomato early blight bacterium | 95 | 65.5 | 58.6 |
| Cucumber fusarium axysporum | 53.1 | 65.6 | 62.5 |
| The ring rot of apple bacterium | 69.7 | 68.2 | 90.3 |
| Sclerotinia sclerotiorum | 56.7 | 91 | 88.1 |
| The miliary damping-off germ | 94.7 | 94.7 | 94.7 |
| Cereal silk nuclear germ | 93 | 93 | 93 |
Biological activity is with killing or suppressing percentage and represent in table 2, the table 3
Active classification: +++〉=90%; ++ 〉=70%-89%; + 〉=50%-69%;-＜50%.
26 kind of plant pathogenic fungi biomass growth rate restraining effect are found that The compounds of this invention has suppress the agricultural fungal diseases activity preferably, under 5.0ug/mL concentration, the mycothallus growth for examination there is the good restraining effect, the inhibiting rate overwhelming majority is more than 80%, even reach 100.0%, with the Zui Hao of current fungistatic effect De Difenoconazole (difenoconazole), tebuconazole (difenoconazole) is suitable; Under 1.0ug/mL concentration, the mycothallus growth for examination also there is the good restraining effect, the inhibiting rate overwhelming majority is more than 80%, its effect slightly is inferior to 5.0ug/mL concentration, but its concentration is low, residual quantity is little, substantially reach the inhibition effect, also can with the Zui Hao of current fungistatic effect De Difenoconazole (difenoconazole), tebuconazole (difenoconazole) is suitable.
Claims (10)
1, a kind of two triazole compounds of aryl oxide that contain is characterized in that having following structural formula (I) or described structural formula (I) acceptable enantiomorph on agricultural pharmacology:
Wherein, R
1, R
2, R
3, R
4, R
5, R
6Be hydrogen, C
1～4Alkyl, trifluoromethyl, methoxyl group, nitro or halogen;
Described C
1～4Alkyl is methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl or the tertiary butyl;
Described halogen atom is fluorine, chlorine, bromine or iodine.
2, the two triazole compounds of aryl oxide that contain as claimed in claim 1 is characterized in that described R
1, R
2, R
3, R
4, R
5, R
6In the substituting group, have at least two substituting groups different.
3, the two triazole compounds of aryl oxide that contain as claimed in claim 1 is characterized in that described R
1, R
2, R
3, R
4, R
5, R
6In the substituting group, have at least two substituting groups identical.
4, the acid salt that contains the two triazole compounds of aryl oxide as claimed in claim 1, it is characterized in that the acid of described acid salt is one or more in hydrochloric acid, Hydrogen bromide, nitric acid, sulfuric acid, phosphoric acid, hydroiodic acid HI, hydrofluoric acid, perchloric acid, tosic acid, methylsulfonic acid, acetate, citric acid, tartrate, oxysuccinic acid, oxalic acid, fumaric acid or the phthalic acid.
5, the metal-salt mixture of the two triazole compounds of aryl oxide according to claim 1 is characterized in that having following structural formula (II):
Wherein, R
1, R
2, R
3, R
4, R
5, R
6Be hydrogen, C
1～4Alkyl, trifluoromethyl, methoxyl group, nitro or halogen;
Described C
1～4Alkyl is methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl or the tertiary butyl;
Described halogen atom is fluorine, chlorine, bromine or iodine;
Described M is the period of element Table II
A, IV
A, I
B, II
B, VI
B, VII
BOr the positively charged ion of VIII family;
Described Y is the negatively charged ion of neutralizing cation M electric charge.
6, as among the claim 1-3 any one described contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
7, as claimed in claim 6 contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease, it is characterized in that described agroforestry fungal disease is fungus-caused by the one or more genus that are under the jurisdiction of Ascomycota, Basidiomycota, imperfect fungi door.
8, as claimed in claim 7 contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease, it is characterized in that, described agroforestry fungal disease be by Staphlosporonites, interlink spore genus, black star spore genus, Verticillium, reaping hook belongs to or the spherical shell spore belongs to, and one or more are fungus-caused.
9, the acid salt that contains the two triazole compounds of aryl oxide as claimed in claim 4 as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
10, the metal-salt mixture of the two triazole compounds of aryl oxide as claimed in claim 5 as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101408367A CN100451007C (en) | 2006-10-12 | 2006-10-12 | compound containing aromatic ether and ditriazole and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101408367A CN100451007C (en) | 2006-10-12 | 2006-10-12 | compound containing aromatic ether and ditriazole and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1923819A true CN1923819A (en) | 2007-03-07 |
| CN100451007C CN100451007C (en) | 2009-01-14 |
Family
ID=37816660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006101408367A Active CN100451007C (en) | 2006-10-12 | 2006-10-12 | compound containing aromatic ether and ditriazole and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100451007C (en) |
Cited By (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102657199A (en) * | 2012-05-08 | 2012-09-12 | 杭州宇龙化工有限公司 | Sterilization composition containing difenodiconazole and pyraclostrobin |
| CN102657184A (en) * | 2012-04-19 | 2012-09-12 | 杭州宇龙化工有限公司 | Sterilizing composition containing phenylate diazole and thifluzamide |
| CN102657179A (en) * | 2012-04-26 | 2012-09-12 | 杭州宇龙化工有限公司 | Sterilization composition containing phenylate diazole and trifloxystrobin |
| CN102696621A (en) * | 2012-05-30 | 2012-10-03 | 杭州宇龙化工有限公司 | Bactericidal composition containing difenodiconazole and prothioconazole |
| CN102696626A (en) * | 2012-07-10 | 2012-10-03 | 杭州宇龙化工有限公司 | Sterilization composition containing phenylate diazole and fludioxonil |
| CN102696625A (en) * | 2012-06-28 | 2012-10-03 | 杭州宇龙化工有限公司 | Sterilization composition containing difenoconazole and picoxystrobin and application of sterilization composition |
| CN102696628A (en) * | 2012-07-10 | 2012-10-03 | 杭州宇龙化工有限公司 | Sterilization combination containing phenylate diazole and cyprodinil |
| CN102696627A (en) * | 2012-07-10 | 2012-10-03 | 杭州宇龙化工有限公司 | Sterilization composition containing phenylate diazole and thiabendazole |
| CN102696623A (en) * | 2012-06-21 | 2012-10-03 | 杭州宇龙化工有限公司 | Bactericidal composition containing phenylate bioxazoline and propiconazole |
| CN102715173A (en) * | 2012-06-28 | 2012-10-10 | 杭州宇龙化工有限公司 | Bactericidal composition containing phenylate diazole and fluoxastrobin and application of bactericidal composition |
| CN102715168A (en) * | 2012-06-28 | 2012-10-10 | 杭州宇龙化工有限公司 | Sterilization combination containing phenylate diazole and azoxystrobin and application thereof |
| CN102754649A (en) * | 2012-08-01 | 2012-10-31 | 杭州宇龙化工有限公司 | Sterilizing composition containing phenylate bi (imidazole) and epoxiconazole |
| WO2014082881A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| WO2014082871A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| WO2014124850A1 (en) | 2013-02-14 | 2014-08-21 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2783569A1 (en) | 2013-03-28 | 2014-10-01 | Basf Se | Compositions comprising a triazole compound |
| WO2014184309A1 (en) * | 2013-05-17 | 2014-11-20 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2813499A1 (en) | 2013-06-12 | 2014-12-17 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| WO2014198557A1 (en) * | 2013-06-12 | 2014-12-18 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| WO2014198553A1 (en) * | 2013-06-12 | 2014-12-18 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| CN104604904A (en) * | 2015-02-16 | 2015-05-13 | 杭州宇龙化工有限公司 | Bactericidal composition containing difenodiconazole and mancozeb |
| CN104604886A (en) * | 2015-02-16 | 2015-05-13 | 杭州宇龙化工有限公司 | Bactericidal composition containing difenodiconazole and bupirimate |
| CN104604888A (en) * | 2015-02-16 | 2015-05-13 | 杭州宇龙化工有限公司 | Bactericidal composition containing difenodiconazole and famoxadone |
| CN104663685A (en) * | 2015-02-16 | 2015-06-03 | 杭州宇龙化工有限公司 | Bactericidal composition containing phenylate diazole and benthiavalicarb |
| CN104686527A (en) * | 2015-02-16 | 2015-06-10 | 杭州宇龙化工有限公司 | Fungicidal composition containing phenyl ether bisimidazole and zoxamide |
| CN104829546A (en) * | 2015-04-13 | 2015-08-12 | 天津师范大学 | Double-triazole substituted ethoxy benzene compound and preparation method and application thereof |
| CN105254577A (en) * | 2015-08-07 | 2016-01-20 | 常州大学 | Bis-triazole-substituted terephthalate compound and its preparation method and use |
| CN105669575A (en) * | 2016-03-08 | 2016-06-15 | 华中师范大学 | 3-(1,2,3-triazole-4-yl)-2-(1,2,4-triazole-1-yl) propyl alcohol compound as well as preparation method and application thereof |
| CN105994384A (en) * | 2016-05-21 | 2016-10-12 | 张素香 | Sterilizing composition |
| CN110810424A (en) * | 2018-08-10 | 2020-02-21 | 江苏龙灯化学有限公司 | Bactericidal composition |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2078719B (en) * | 1980-06-02 | 1984-04-26 | Ici Ltd | Heterocyclic compounds |
| US4466974A (en) * | 1982-11-16 | 1984-08-21 | Pfizer Inc. | Bistriazole antifungal agents |
| EP0275955B1 (en) * | 1987-01-21 | 1990-07-04 | Ciba-Geigy Ag | Microbicidal composition |
| US5665751A (en) * | 1995-06-07 | 1997-09-09 | The Procter & Gamble Company | Pharmaceutical composition for inhibiting the growth of cancers |
-
2006
- 2006-10-12 CN CNB2006101408367A patent/CN100451007C/en active Active
Cited By (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102657184A (en) * | 2012-04-19 | 2012-09-12 | 杭州宇龙化工有限公司 | Sterilizing composition containing phenylate diazole and thifluzamide |
| CN102657184B (en) * | 2012-04-19 | 2014-01-22 | 杭州宇龙化工有限公司 | Sterilizing composition containing phenylate diazole and thifluzamide |
| CN102657179A (en) * | 2012-04-26 | 2012-09-12 | 杭州宇龙化工有限公司 | Sterilization composition containing phenylate diazole and trifloxystrobin |
| CN102657179B (en) * | 2012-04-26 | 2014-04-23 | 杭州宇龙化工有限公司 | Sterilization composition containing phenylate diazole and trifloxystrobin |
| CN102657199A (en) * | 2012-05-08 | 2012-09-12 | 杭州宇龙化工有限公司 | Sterilization composition containing difenodiconazole and pyraclostrobin |
| CN102657199B (en) * | 2012-05-08 | 2013-08-07 | 杭州宇龙化工有限公司 | Sterilization composition containing difenodiconazole and pyraclostrobin |
| CN102696621A (en) * | 2012-05-30 | 2012-10-03 | 杭州宇龙化工有限公司 | Bactericidal composition containing difenodiconazole and prothioconazole |
| CN102696621B (en) * | 2012-05-30 | 2013-06-12 | 杭州宇龙化工有限公司 | Bactericidal composition containing difenodiconazole and prothioconazole |
| CN102696623A (en) * | 2012-06-21 | 2012-10-03 | 杭州宇龙化工有限公司 | Bactericidal composition containing phenylate bioxazoline and propiconazole |
| CN102715173A (en) * | 2012-06-28 | 2012-10-10 | 杭州宇龙化工有限公司 | Bactericidal composition containing phenylate diazole and fluoxastrobin and application of bactericidal composition |
| CN102715168A (en) * | 2012-06-28 | 2012-10-10 | 杭州宇龙化工有限公司 | Sterilization combination containing phenylate diazole and azoxystrobin and application thereof |
| CN102715168B (en) * | 2012-06-28 | 2013-09-04 | 杭州宇龙化工有限公司 | Sterilization combination containing phenylate diazole and azoxystrobin and application thereof |
| CN102715173B (en) * | 2012-06-28 | 2013-11-13 | 杭州宇龙化工有限公司 | Bactericidal composition containing phenylate diazole and fluoxastrobin and application of bactericidal composition |
| CN102696625A (en) * | 2012-06-28 | 2012-10-03 | 杭州宇龙化工有限公司 | Sterilization composition containing difenoconazole and picoxystrobin and application of sterilization composition |
| CN102696627A (en) * | 2012-07-10 | 2012-10-03 | 杭州宇龙化工有限公司 | Sterilization composition containing phenylate diazole and thiabendazole |
| CN102696626B (en) * | 2012-07-10 | 2013-07-03 | 杭州宇龙化工有限公司 | Sterilization composition containing phenylate diazole and fludioxonil |
| CN102696628A (en) * | 2012-07-10 | 2012-10-03 | 杭州宇龙化工有限公司 | Sterilization combination containing phenylate diazole and cyprodinil |
| CN102696626A (en) * | 2012-07-10 | 2012-10-03 | 杭州宇龙化工有限公司 | Sterilization composition containing phenylate diazole and fludioxonil |
| CN102754649A (en) * | 2012-08-01 | 2012-10-31 | 杭州宇龙化工有限公司 | Sterilizing composition containing phenylate bi (imidazole) and epoxiconazole |
| WO2014082871A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| WO2014082881A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| WO2014124850A1 (en) | 2013-02-14 | 2014-08-21 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2783569A1 (en) | 2013-03-28 | 2014-10-01 | Basf Se | Compositions comprising a triazole compound |
| WO2014184309A1 (en) * | 2013-05-17 | 2014-11-20 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2813499A1 (en) | 2013-06-12 | 2014-12-17 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| WO2014198557A1 (en) * | 2013-06-12 | 2014-12-18 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| WO2014198553A1 (en) * | 2013-06-12 | 2014-12-18 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| CN104663685A (en) * | 2015-02-16 | 2015-06-03 | 杭州宇龙化工有限公司 | Bactericidal composition containing phenylate diazole and benthiavalicarb |
| CN104604888B (en) * | 2015-02-16 | 2016-07-06 | 杭州宇龙化工有限公司 | A kind of bactericidal composition containing difenodiconazole Yu Famoxate |
| CN104604888A (en) * | 2015-02-16 | 2015-05-13 | 杭州宇龙化工有限公司 | Bactericidal composition containing difenodiconazole and famoxadone |
| CN104604904A (en) * | 2015-02-16 | 2015-05-13 | 杭州宇龙化工有限公司 | Bactericidal composition containing difenodiconazole and mancozeb |
| CN104686527A (en) * | 2015-02-16 | 2015-06-10 | 杭州宇龙化工有限公司 | Fungicidal composition containing phenyl ether bisimidazole and zoxamide |
| CN104604886A (en) * | 2015-02-16 | 2015-05-13 | 杭州宇龙化工有限公司 | Bactericidal composition containing difenodiconazole and bupirimate |
| CN104829546B (en) * | 2015-04-13 | 2017-03-15 | 天津师范大学 | Ethoxybenzene compound that double triazoles replace and preparation method and application |
| CN104829546A (en) * | 2015-04-13 | 2015-08-12 | 天津师范大学 | Double-triazole substituted ethoxy benzene compound and preparation method and application thereof |
| CN105254577A (en) * | 2015-08-07 | 2016-01-20 | 常州大学 | Bis-triazole-substituted terephthalate compound and its preparation method and use |
| CN105254577B (en) * | 2015-08-07 | 2017-08-01 | 常州大学 | A kind of pair of triazole substituted benzene diformic ester compound, preparation method and purposes |
| CN105669575A (en) * | 2016-03-08 | 2016-06-15 | 华中师范大学 | 3-(1,2,3-triazole-4-yl)-2-(1,2,4-triazole-1-yl) propyl alcohol compound as well as preparation method and application thereof |
| CN105669575B (en) * | 2016-03-08 | 2018-06-15 | 华中师范大学 | 3- (1,2,3-triazoles -4- bases) -2- (1,2,4- triazol-1-yl) propanol compound and preparation method thereof and purposes |
| CN105994384A (en) * | 2016-05-21 | 2016-10-12 | 张素香 | Sterilizing composition |
| CN110810424A (en) * | 2018-08-10 | 2020-02-21 | 江苏龙灯化学有限公司 | Bactericidal composition |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100451007C (en) | 2009-01-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1923819A (en) | compound containing aromatic ether and ditriazole and use thereof | |
| CN101225074A (en) | Synthesis of compound containing aryl ether triazole | |
| CN1309897A (en) | Unsaturated oximino ether bactericide | |
| CN1814590A (en) | N-(2-substituted phenyl)-N-methoxy carbamate compounds and their preparation and use | |
| CN1193321A (en) | Microbiocidal benzotriazoles compounds | |
| US20200093130A1 (en) | Application of tetrahydrobenzazole in preparation of agricultural fungicide or fungicide composition and preparation method thereof | |
| US3291683A (en) | Controlling fungi and bacteria with alkoxy or alkylthio alkylamine ethers | |
| CN1261026C (en) | Bacteridal composition containing alkene oxime amine and triazole kind compound | |
| DE69402223T2 (en) | Antimicrobial and fungicidal compositions containing silicon compounds, and their use in agriculture and horticulture | |
| CN103524417A (en) | 3-methyl-4-formyl pyrazol compounds | |
| CN1035254C (en) | Substituted thiophenecarboxamides | |
| CN1308294C (en) | Substituted acetophenone oxime derivative and preparation process and use thereof | |
| CN109666004B (en) | Trifluoromethyl-containing pyrazinamide compounds, preparation method and application thereof, and bactericide | |
| CN103554026B (en) | One group of 3-trifluoromethyl-4-formyl pyrazole compound | |
| CN1278254A (en) | Thiadiazole carboxamide derivative, plant disease controlling agent and method of using same | |
| CN111763231B (en) | Synthesis method and application of triphenyl phosphonium cation-containing bactericidal and acaricidal compound | |
| CA1274545A (en) | 3-(3-iodopropargyloxy)-propionitrile, a process for its preparation and its use | |
| CS236480B2 (en) | Agent with fungicide and bactericide effect | |
| CN1027894C (en) | Synthetic method of 1-cyclohexyl dibutyl tin-1, 2, 4-triazole | |
| CN103709104A (en) | Imidazole compound for sterilization as well as preparation method and application thereof | |
| CN1062907A (en) | 2-(3-oxo pyridine base)-1,3-dioxolane and two hydride compounds, composition and control fungi method | |
| CN106749205B (en) | A kind of pyridine ethoxy coumarin class plant growth regulator | |
| JPS6072870A (en) | Triazole ethanols | |
| CN1035660A (en) | 2, the preparation and the application thereof of 6-dimethyl benzene hydrazine derivative | |
| CN110122495A (en) | Compound containing 1- (3- chloro-2-pyridyl) -1 hydrogen-pyrazoles active fragment is preparing the application in fungicide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| ASS | Succession or assignment of patent right |
Owner name: HANGZHOU YULONG CHEMICAL ENGINEERING CO., LTD. Free format text: FORMER OWNER: QINGDAO UNIVERSITY OF SCIENCE AND TECHNOLOGY Effective date: 20080711 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20080711 Address after: Industrial Development Zone, Tangqi Town, Yuhang District, Zhejiang, Hangzhou Province, China: 311106 Applicant after: Hangzhou Udragon Chemical Co.,Ltd. Address before: 53, Zhengzhou Road, Shandong, Qingdao Province, China: 266071 Applicant before: QINGDAO University OF SCIENCE AND TECHNOLOGY |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address |
Address after: 311106 No. 172, Zhangjiadun Road, Tangqi Town, Linping District, Hangzhou, Zhejiang Patentee after: Zhejiang Yulong Pharmaceutical Co.,Ltd. Address before: 311106 Industrial Development Zone, Tangqi Town, Yuhang District, Zhejiang, Hangzhou Patentee before: Hangzhou Udragon Chemical Co.,Ltd. |
|
| CP03 | Change of name, title or address |