CN111548319B - 1, 1-dicyanooxime ether compound and application thereof - Google Patents
1, 1-dicyanooxime ether compound and application thereof Download PDFInfo
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- CN111548319B CN111548319B CN202010078417.5A CN202010078417A CN111548319B CN 111548319 B CN111548319 B CN 111548319B CN 202010078417 A CN202010078417 A CN 202010078417A CN 111548319 B CN111548319 B CN 111548319B
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- -1 ether compound Chemical class 0.000 title claims abstract description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 13
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 7
- 208000031888 Mycoses Diseases 0.000 claims abstract description 4
- 239000003899 bactericide agent Substances 0.000 claims abstract description 3
- 230000001580 bacterial effect Effects 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 240000007594 Oryza sativa Species 0.000 claims description 11
- 235000007164 Oryza sativa Nutrition 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 235000009566 rice Nutrition 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 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 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 8
- 240000008067 Cucumis sativus Species 0.000 claims description 7
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
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- 150000003839 salts Chemical class 0.000 claims description 6
- 235000013399 edible fruits Nutrition 0.000 claims description 5
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
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- 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 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- 235000011087 fumaric acid Nutrition 0.000 claims description 4
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 239000004310 lactic acid Substances 0.000 claims description 4
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 4
- 235000011007 phosphoric acid Nutrition 0.000 claims description 4
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- 229960004889 salicylic acid Drugs 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 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
- 229940005605 valeric acid Drugs 0.000 claims description 4
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 206010039509 Scab Diseases 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
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- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
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- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000002888 effect on disease Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000013537 high throughput screening Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- 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
- A01N37/50—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 the nitrogen atom being doubly bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
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- Chemical & Material Sciences (AREA)
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- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
The invention discloses a 1, 1-dicyanooxime ether compound, the structure of which is shown as a general formula I, wherein the definition of each substituent group in the formula I is shown in the specification.
Description
Technical Field
The invention belongs to the field of agricultural bactericides, and particularly relates to a 1, 1-dicyanooxime ether compound and application thereof.
Background
Patent CN201611199611.9 discloses a compound of the following general formula, which has a certain bactericidal activity.
The bactericidal activity, in particular the bactericidal activity, of the compounds disclosed in the prior art is not satisfactory and needs to be continuously studied in order to satisfy the practical application.
In the prior art, the 1, 1-dicyanooxime ether compound shown in the invention has no reported bactericidal activity.
Disclosure of Invention
The invention aims to provide a 1, 1-dicyanooxime ether compound capable of controlling various plant bacterial diseases and fungal diseases, and a medicament for preparing the same in agriculture and other fields.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
the 1, 1-dicyanooxime ether compound is characterized by being shown in a general formula I:
wherein:
w is selected from W 1 -W 4 One of the groups shown:
;
q is selected from Q 1 -Q 3 One of the groups shown, and, #1 is linked to W, #2 is linked to methylene,
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 、X 7 、X 8 、X 9 、X 10 、X 11 、X 12 、X 13 、X 14 、X 15 、X 16 、X 17 each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C 1 -C 6 Alkyl, C 3 -C 6 Cycloalkyl, halo C 1 -C 6 Alkyl, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy, C 1 -C 6 Alkylthio, halo C 1 -C 6 Alkylthio, C 1 -C 6 Alkylamino, C 1 -C 6 Dialkylamino, C 1 -C 6 Alkylcarbonyl or C 1 -C 6 An alkoxycarbonyl group;
or salts of compounds of formula I.
The 1, 1-dicyanooxime ether compound of the invention can be further represented by the general formula I:
w is selected from W 1 -W 4 One of the groups shown;
q is selected from Q 1 -Q 3 One of the groups shown;
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 、X 7 、X 8 、X 9 、X 10 、X 11 、X 12 、X 13 、X 14 、X 15 、X 16 、X 17 each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C 1 -C 4 Alkyl, C 3 -C 4 Cycloalkyl, halo C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy, C 1 -C 4 Alkylthio, halo C 1 -C 4 Alkylthio, C 1 -C 4 Alkylamino, C 1 -C 4 Dialkylamino, C 1 -C 4 Alkylcarbonyl or C 1 -C 4 An alkoxycarbonyl group;
or salts of compounds of the general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid or citric acid.
The 1, 1-dicyanooxime ether compound of the invention can be further represented by the general formula I:
w is selected from W 1 -W 4 One of the groups shown;
q is selected from Q 1 -Q 3 One of the groups shown;
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 、X 7 、X 8 、X 9 、X 10 、X 11 、X 12 、X 13 、X 14 、X 15 、X 16 、X 17 each independently selected from hydrogen, fluoro, chloro, bromo, cyano, nitro, hydroxy, mercapto, amino, carboxy, methyl, ethyl, N-propyl, isopropyl, cyclopropyl, N-butyl, isobutyl, sec-butyl, tert-butyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2, 2-trifluoroethyl, heptafluoroisopropyl, methoxy, ethoxy, N-propoxy, isopropoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, trifluoromethylthio, 2,2, 2-trifluoroethylthio, methylamino, ethylamino or N, N-dimethylamino;
or salts of compounds of the general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid or citric acid.
In the definitions of the compounds of the general formula given above, the terms used in the collection generally represent the following substituents:
halogen: refers to fluorine, chlorine, bromine or iodine.
Alkyl: straight or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl or different butyl, pentyl or hexyl isomers, etc.
Cycloalkyl: a substituted or unsubstituted cyclic alkyl group such as cyclopropyl, cyclopentyl or cyclohexyl; substituents such as methyl, halogen, and the like.
Haloalkyl: straight or branched alkyl groups, the hydrogen atoms on these alkyl groups may be partially or fully substituted by halogen, such as monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2, 2-trifluoroethyl, heptafluoroisopropyl and the like.
An alkoxy group: a linear or branched alkyl group linked to the structure via an oxygen atom bond, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy and the like.
Haloalkoxy: straight-chain or branched alkoxy groups, the hydrogen atoms on these alkoxy groups may be partially or completely substituted by halogen, such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, 2,2, 2-trifluoroethoxy and the like.
Alkylthio: a linear or branched alkyl group linked to the structure via a sulfur atom bond, such as methylthio, ethylthio, and the like.
Haloalkylthio: straight-chain or branched alkylthio groups, the hydrogen atoms on these alkylthio groups may be partially or wholly substituted with halogen, for example difluoromethylthio, trifluoromethylthio, 2,2, 2-trifluoroethylthio and the like.
Alkylamino: a linear or branched alkyl group linked to the structure via a nitrogen atom bond, such as methylamino, ethylamino, n-propylamino, isopropylamino or isomerised butylamine.
Dialkylamino group: two identical or different linear or branched alkyl groups are bonded to the structure via a nitrogen atom bond, such as N, N-dimethylamino, N-methyl-N-ethylamino, etc.
Alkylcarbonyl: the alkyl group is attached to the structure via a carbonyl group, such as acetyl (CH 3 CO-), n-propionyl (CH 3CH2 CO-), and the like.
Alkoxycarbonyl: alkyl-O-CO-, e.g. methoxycarbonyl (CH) 3 OCO-), ethoxycarbonyl (CH) 3 CH 2 OCO-), n-propoxycarbonyl (CH) 3 CH 2 CH 2 OCO-), n-butoxycarbonyl group (CH) 3 CH 2 CH 2 CH 2 OCO-) and the like.
Some of the compounds of the general formula I of the present invention are shown in tables 1 to 6, but the present invention is by no means limited to these compounds.
In formula I, when w=w 1 And q=q 1 In this case, the general formula I may be represented by the general formulae I to W 1 -Q 1 Representation (for convenience of description, W 1 Substituent X of (2) 1 、X 2 、X 3 、X 4 、X 5 Represented by R, supra).
Table 1: general formula I-W 1 -Q 1 Wherein R is different substituent groups shown in Table 1, and the number of the representative compounds is 1.1-1.354.
TABLE 1
In formula I, when w=w 1 And q=q 2 In this case, the formula I may be represented by the formula I-W 1 -Q 2 Representative compounds are shown in Table 2.
Table 2: general formula I-W 1 -Q 2 In which the substituents R correspond to Table 1 and represent the compound numbers 2.1 to 2.354, which correspond in turn to Table 1 from 1.1 to 1.354.
In formula I, when w=w 1 And q=q 3 In this case, the formula I may be represented by the formula I-W 1 -Q 3 Representative compounds are shown in Table 3.
Table 3: general formula I-W 1 -Q 3 In which the substituent R is the same as Table 1 and represents compound numbers 3.1 to 3.354, which correspond to 1.1 to 1.354 of Table 1 in order.
In formula I, when w=w 2 In this case, the formula I may be represented by the formula I-W 2 Representative compounds are shown in table 4:
TABLE 4 Table 4
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In formula I, when w=w 3 In this case, the formula I may be represented by the formula I-W 3 Representative compounds are shown in table 5:
TABLE 5
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In formula I, when w=w 4 In this case, the formula I may be represented by the formula I-W 4 Representative compounds are shown in table 6:
TABLE 6
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The physicochemical properties, nuclear magnetic data and mass spectrum data of a part of the compounds of the invention are shown in Table 7:
TABLE 7
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The compounds of the invention of the general formula I when Q is Q 1 When the compound of the general formula I is shown as the general formula I-1; when Q is Q 2 When the compound of the general formula I is shown as the general formula I-2; when Q is Q 3 When the compounds of the formula I are represented by the formula I-3, they can be prepared in accordance with the following method (in the formula, M represents a cation, e.g. Na, unless otherwise indicated + 、K + 、CS + 、Ag + Or NH 4 + Etc.):
the compound of the general formula II-1, the compound of the general formula II-2 and the compound of the general formula II-3 respectively react with the compound of the general formula III in a proper solvent at the temperature ranging from minus 10 ℃ to the boiling point of the solvent for 0.5 to 48 hours to respectively prepare the compound of the general formula I-1, the compound of the general formula I-2 and the compound of the general formula I-3. Suitable solvents may be the same or different and are selected from alcohols (e.g., methanol, ethanol, etc.), aromatic hydrocarbons (e.g., benzene, toluene, xylene, etc.), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), halogenated hydrocarbons (e.g., methylene chloride, etc., chloroform, carbon tetrachloride, etc.), esters (e.g., methyl acetate, ethyl acetate, etc.), ethers (e.g., tetrahydrofuran, dioxane, diethyl ether, 1, 2-dimethoxyethane, etc.), polar solvents (e.g., water, acetonitrile, dioxane, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, etc.), or mixtures of the above solvents.
Compounds of formula II-1 may be prepared according to known methods (e.g., european Journal of Medicinal Chemistry, 46 (4), 1367-1373; 2011, new Journal of Chemistry, 41 (13), 5875-5883; 2017, tetrahedron Letters, 58 (1), 87-91; 2017, bioorganic & Medicinal Chemistry Letters, 24 (22), 5154-5156; 2014 or CN103864769, etc. reported methods).
The compounds of formula II-2 may be prepared according to known methods (e.g., methods reported for Journal of Agricultural and Food Chemistry, 53 (8), 3120-3125; 2005, european Journal of Medicinal Chemistry, 113, 246-257; 2016, CN104844532 or CN105017242, etc.).
The compounds of formula II-3 may be prepared according to known methods (e.g., pharmaceutical Chemistry Journal, 50 (4), 234-238; 2016, new Journal of Chemistry, 41 (13), 5875-5883; 2017, journal of Medicinal Chemistry, 56 (10), 3783-3805; 2013 or WO2012129564, etc., as reported).
The compounds of formula III may be prepared according to known methods (e.g. as reported in CN103804321, WO2008139481, U.S. Pat. No. 3, 20130096098 or Journal of the Chemical Society of Pakistan, 33 (3), 324-332, 2011, etc.).
The compound shown in the general formula I can be used for controlling various plant bacterial diseases, such as fruit blotch (such as melon and fruit blotch and the like), leaf blotch (such as tomato bacterial leaf blotch and the like), bacterial wilt (such as tomato bacterial wilt and potato bacterial wilt and the like), bacterial blight, canker (such as citrus canker and kiwi canker and the like), soft rot (such as celery cabbage soft rot and the like), bacterial angular blotch (such as cucumber bacterial angular blotch and the like), bacterial leaf blotch (such as rice bacterial leaf blotch and the like), leaf blight, bacterial leaf blight (such as rice bacterial leaf blotch and the like), wild fire disease, bacterial scab and the like.
The compound can also be used for preventing and treating diseases caused by various fungi such as oomycetes, basidiomycetes, ascomycetes, fungi imperfecti and the like on various crops, for example, the compound has good prevention effect on diseases such as cucumber downy mildew, cucumber gray mold, cucumber anthracnose, cucumber powdery mildew, tomato early blight, tomato late blight, pepper blight, grape downy mildew, grape white rot, apple ring rot, apple alternaria leaf spot, rice sheath blight, rice blast, wheat rust, wheat leaf spot, wheat powdery mildew, rape sclerotinia, corn small spot and the like at a lower dosage.
The invention also provides a bactericidal composition, wherein the bactericidal composition is also provided with a compound shown in a general formula I and an agriculturally acceptable carrier, and the weight percentage of active components in the bactericidal composition is 0.1-99%.
The invention also provides a process for the preparation of a composition as defined above: the compound of formula I is admixed with a carrier. Such compositions may be comprised of a single compound of the invention or a mixture of compounds.
The carrier in the composition of the invention is a substance that satisfies the following conditions: it is formulated with the active ingredient and applied to the locus to be treated, for example, it may be a plant, seed or soil; or to facilitate storage, transport or handling. The carrier may be a solid or a liquid, including substances that are normally gaseous but which have been compressed into a liquid, and commonly used in formulating insecticidal and fungicidal compositions.
Suitable solid carriers include natural or synthetic clays or silicates, such as diatomaceous earth, talc, attapulgite, aluminum silicate (kaolin), montmorillonite, mica; calcium carbonate; calcium sulfate; ammonium sulfate; synthetic silica, synthetic calcium silicate or aluminum silicate; elements such as carbon and sulfur; natural or synthetic resins such as coumarone resins, polyvinyl chloride, styrene polymers or copolymers; solid polychlorinated phenol; asphalt; waxes such as beeswax, paraffin wax.
Suitable liquid carriers include water; alcohols such as isopropanol, ethanol; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone, cyclohexyl ketone; an ether; aromatic hydrocarbons such as benzene, toluene, xylene; petroleum fractions such as kerosene, mineral oil; chlorinated hydrocarbons such as carbon tetrachloride, perchloroethylene and trichloroethylene. In general, mixtures of these liquids are also suitable.
Detailed Description
The following specific examples serve to further illustrate the invention, but the invention is by no means limited to these examples. (the raw materials used are commercially available unless otherwise noted)
Synthetic examples
According to the synthetic route, the compounds shown in the general formula I of the invention can be prepared and obtained respectively by adopting different raw material compounds, and the following is further specifically described:
example 1: preparation of Compound 1.354
To a 50 ml reaction flask were added 2-chloromethyl-5-phenyl-1, 3, 4-oxadiazole (0.50 g, 2.58 mmol), malononitrile oxime ether sodium salt (0.34 g, 2.91 mmol) and 20 ml acetonitrile and the reaction was stirred at room temperature. After the reaction was completed, acetonitrile was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 0.44 g of a white solid.
Example 2: preparation of Compound 2.354
To a 50 ml reaction flask were added 2-chloromethyl-5-phenyl-1, 3, 4-thiadiazole (0.30 g, 1.43 mmol), malononitrile oxime ether sodium salt (0.20 g, 1.71 mmol) and 20 ml acetonitrile and the reaction was stirred at room temperature. After the reaction was completed, acetonitrile was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 0.27 g of a yellow solid.
Example 3: preparation of Compound 3.354
To a 50 ml reaction flask were added 5-chloromethyl-3-phenyl-1, 2, 4-oxadiazole (0.35 g, 1.80 mmol), malononitrile oxime ether sodium salt (0.25 g, 2.14 mmol) and 20 ml acetonitrile and the reaction was stirred at room temperature. After the reaction was completed, acetonitrile was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 0.31 g of a white solid.
Other compounds of formula I of the present invention may be prepared by reference to the methods described in the above specific examples and summary.
Biological Activity assay
Example 4: determination of biological Activity against Pyricularia oryzae or Gray mold
In vitro bactericidal activity assay: the high-throughput screening method is adopted, namely, a compound sample of the general formula I is dissolved by a proper solvent (the type of the solvent is such as acetone, methanol, DMF and the like, and is selected according to the dissolving capacity of the solvent to the sample) to prepare a solution with the required concentration to be tested. Under the ultra-clean working environment, the liquid to be detected is added into the micropores of the 96-hole culture plate, then the pathogenic bacteria propagule suspension is added into the micropores, and the treated culture plate is placed in a constant temperature incubator for culture. Investigation was performed 24 hours later, and the germination or growth of the pathogenic bacteria propagules was visually examined at the time of investigation, and the bacteriostatic activity of the compound was evaluated according to the germination or growth of the control treatment.
The test results were as follows:
25 In the case of mg/L of the solution, compounds 1.1, 1.2, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.12, 1.13, 1.15, 1.16, 1.17, 1.18, 1.19, 1.22, 1.25, 1.36, 1.39, 1.40, 1.43, 1.45, 1.88, 1.101, 1.104, 1.106, 1.107, 1.109, 1.110, 1.113, 1.167, 1.295, 1.354, 2.5, 2.6, 2.7, 2.8, 2.18, 2.19 2.22, 2.25, 2.43, 2.45, 2.53, 2.101, 2.104, 2.107, 2.110, 2.113, 2.167, 2.354, 3.1, 3.2, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 3.19, 3.22, 3.25, 3.36, 3.43, 3.45, 3.53, 3.101, 3.107, 3.110, 3.113, 3.354, 5.92 had 100% inhibition of rice blast spore germination.
25 In the case of mg/L of the solution, compounds 1.1, 1.2, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.12, 1.13, 1.15, 1.16, 1.17, 1.18, 1.19, 1.22, 1.25, 1.36, 1.39, 1.40, 1.43, 1.45, 1.88, 1.101, 1.104, 1.106, 1.107, 1.109, 1.110, 1.113, 1.167, 1.295, 1.354, 2.5, 2.6, 2.7, 2.8, 2.18, 2.19 2.22, 2.25, 2.43, 2.45, 2.53, 2.101, 2.104, 2.107, 2.110, 2.113, 2.167, 2.354, 3.1, 3.2, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 3.19, 3.22, 3.25, 3.36, 3.43, 3.45, 3.53, 3.101, 3.107, 3.110, 3.113, 3.354, 5.92 has 100% spore germination inhibition rate for vegetable botrytis.
Example 5: determination of control Effect on plant bacterial diseases
The compound of the invention is used for controlling and measuring various plant bacterial diseases, and the test procedures are as follows:
melon and fruit spot disease: the test compound is dissolved with a small amount of N, N dimethylformamide and diluted with water to the desired concentration. Uniformly mixing pathogenic bacteria cultured to a stationary growth period with a quantitative compound solution, putting melon seeds subjected to germination acceleration into a mixed solution of a bacterial solution and the compound, soaking for half an hour, sowing the seeds into an earthworm soil culture cup, putting the earthworm soil culture cup into a greenhouse for moisture preservation and culture, generally culturing for two weeks, and carrying out control effect investigation after the seeds are fully developed by contrast.
Soft rot of chinese cabbage: cutting 2 cm square leaf of Chinese cabbage, and placing into glass culture dish with double layers of filter paper. Dissolving with N, N dimethylformamide, diluting with water to desired concentration, spraying on the surface of leaf of Chinese cabbage, air drying the liquid medicine on the surface of leaf in a fume hood, needling to form wound on the surface of leaf with inoculating needle, inoculating 5 microliter of soft rot fungus of Chinese cabbage cultured to stationary growth phase into the wound, and inoculating. Finally, the test materials are placed into an incubator for light-shielding cultivation for 48 hours, and the control effect investigation is carried out after the contrast is fully developed.
Bacterial leaf spot of cucumber, bacterial leaf spot of tomato, bacterial leaf streak of rice, bacterial leaf blight of rice: the test compound is dissolved with a small amount of N, N dimethylformamide and diluted with water to the desired concentration. Spraying the compound on the surface of a plant test material, air-drying the surface liquid medicine at a shade place, spraying and inoculating pathogenic bacteria bacterial liquid cultured to a stable growth period on the surface of the plant test material, and then placing the plant test material in a greenhouse for moisture preservation and culture. Usually, the culture is carried out for about ten days, and after the control is fully ill, the control effect investigation is carried out.
Potato scab: a certain amount of the compound to be measured is weighed and dissolved in acetone respectively according to the requirement of a solvent, and then added into water to prepare 100mL of liquid medicine containing 8mg of medicament. Placing potato blocks in a pot filled with bacteria-carrying soil, uniformly spraying 100mL of liquid medicine on the soil and the surfaces of the potato blocks, covering the soil, culturing in a greenhouse, harvesting the potato blocks after about 10 weeks, and carrying out experimental investigation.
The test results were as follows:
600 In the case of mg/L of the solution, compounds 1.1, 1.2, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.12, 1.13, 1.15, 1.16, 1.17, 1.18, 1.19, 1.22, 1.25, 1.36, 1.39, 1.40, 1.43, 1.45, 1.88, 1.101, 1.104, 1.106, 1.107, 1.109, 1.110, 1.113, 1.167, 1.295, 1.354, 2.5, 2.6, 2.7, 2.8, 2.18 2.19, 2.22, 2.25, 2.43, 2.45, 2.53, 2.101, 2.104, 2.107, 2.110, 2.113, 2.167, 2.354, 3.1, 3.2, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 3.19, 3.22, 3.25, 3.36, 3.43, 3.45, 3.53, 3.101, 3.107, 3.110, 3.113, 3.354, 5.92 had a 100% control of melon fruit blotch.
At the time of 400mg/L, the compounds 1.1, 1.2, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.12, 1.13, 1.15, 1.16, 1.17, 1.18, 1.19, 1.22, 1.25, 1.36, 1.39, 1.40, 1.43, 1.45, 1.88, 1.101, 1.104, 1.106, 1.107, 1.109, 1.110, 1.113, 1.167, 1.295, 1.354, 2.5, 2.6, 2.7, 2.8, 2.18, 2.19, 2.22, 2.25, 2.43, 2.45, 2.53, 2.101, 2.104, 2.107, 2.110, 2.113, 2.167, 2.354, 3.1, 3.2, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 3.19, 3.25, 3.35, 3.3.3.45, 3.37, 3.45, 3.37, 3.35, 3.36, 3.3.7, 3.45, 3.35, 3.37, 3.35, 3.7, 3.45, 3.3.35, 3.37, 3.35, 3.45, 3.3.3.7, 3.37, 3.35, 3.7, 3.17, 3.35, 3.101, 3.100% bacterial leaf-white, 3.100, 3.7, 3.100% of rice leaf spot.
At the time of 400mg/L, compounds 1.1, 1.2, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.12, 1.13, 1.15, 1.16, 1.17, 1.18, 1.19, 1.22, 1.25, 1.36, 1.39, 1.40, 1.43, 1.45, 1.88, 1.101, 1.104, 1.106, 1.107, 1.109, 1.110, 1.113, 1.167, 1.295, 1.354, 2.5, 2.6, 2.7, 2.8, 2.18, 2.19, 2.22 2.25, 2.43, 2.45, 2.53, 2.101, 2.104, 2.107, 2.110, 2.113, 2.167, 2.354, 3.1, 3.2, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 3.19, 3.22, 3.25, 3.36, 3.43, 3.45, 3.53, 3.101, 3.107, 3.110, 3.113, 3.354, 5.92 had a 100% control effect on chinese cabbage soft rot and tomato bacterial leaf spot.
At 8 mg/strain concentration, compounds 1.1, 1.2, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.12, 1.13, 1.15, 1.16, 1.17, 1.18, 1.19, 1.22, 1.25, 1.36, 1.39, 1.40, 1.43, 1.45, 1.88, 1.101, 1.104, 1.106, 1.107, 1.109, 1.110, 1.113, 1.167, 1.295, 1.354, 2.5, 2.6, 2.7, 2.8, 2.18, 2.19, 2.22, 2.25, 2.43, 2.45, 2.53, 2.101, 2.104, 2.107, 2.110, 2.113, 2.167, 2.354, 3.1, 3.2, 3.4, 3.5, 3.6, 3.7, 3.8, 3.19, 3.35, 3.36, 3.3.5, 3.45, 3.37, 3.3.37, 3.7, 3.35, 3.45, 3.3.3.3.35, 3.45, 3.37, 3.7, 3.35, 3.3.3.3.5, 3.3.35, 3.3.3.7, 3.35, 3.35.3.35, 3.3.3.5.3.3.7, 3.37, 3.7, 3.8, 3.9.9.17, 3.35.37.37.35.37.37, 3.3.3.5.5, 3.37, 3.3.3.3.3.3.3.3.3.3.3.3.3.3.3.3.37 mg.
Claims (8)
1. The 1, 1-dicyanooxime ether compound is characterized by being shown in a general formula I:
wherein:
w is selected from W 1 、W 3 One of the groups shown:
q is selected from Q 1 -Q 3 One of the groups shown, and, #1 is linked to W, #2 is linked to methylene,
X 1 、X 2 、X 3 、X 4 、X 5 each independently selected from hydrogen, halogen, cyano, nitro, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy, C 1 -C 4 A dialkylamino group;
X 10 、X 11 、X 12 、X 13 each independently selected from hydrogen, halogen;
or salts of compounds of formula I.
2. A compound according to claim 1, wherein in formula I,
w is selected from W 1 、W 3 One of the groups shown;
q is selected from Q 1 -Q 3 One of the groups shown;
X 1 、X 2 、X 3 、X 4 、X 5 each independently selected from hydrogen, halogen, cyano, nitro, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy, C 1 -C 4 A dialkylamino group;
X 10 、X 11 、X 12 、X 13 each independently selected from hydrogen, fluorine, chlorine, bromine;
or salts of compounds of the general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid or citric acid.
3. A compound according to claim 2, wherein in formula I,
w is selected from W 1 、W 3 One of the groups shown;
q is selected from Q 1 -Q 3 One of the groups shown;
X 1 、X 2 、X 3 、X 4 、X 5 each independently selected from hydrogen, fluoro, chloro, bromo, cyano, nitro, methyl, ethyl, N-propyl, isopropyl, N-butyl, isobutyl, sec-butyl, tert-butyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2-trifluoroethyl, heptafluoroisopropyl, methoxy, ethoxy, N-propoxy, isopropoxy, difluoromethoxy, trifluoromethoxy or N, N-dimethylamino;
X 10 、X 11 、X 12 、X 13 each independently selected from hydrogen, fluorine, chlorine;
or salts of compounds of the general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid or citric acid.
4. The compound according to claim 1, wherein the compound of formula I is selected from the group consisting of:
5. use of a compound according to claim 1 as a bactericide for controlling bacterial diseases in the agricultural and forestry fields; the bacterial disease is selected from the group consisting of melon and fruit blotch, cucumber bacterial angular blotch, rice bacterial leaf spot, rice bacterial leaf blight and potato scab.
6. Use of a compound according to claim 1 as fungicide for controlling fungal diseases in the agricultural, forestry fields; the fungal disease is selected from rice blast.
7. A bactericidal composition characterized in that: the composition comprises the compound of the general formula I as defined in claim 1 and an agriculturally acceptable carrier, wherein the weight percentage of active components in the composition is 0.1-99%.
8. A method for controlling pathogens, characterized by: a fungicidal effective amount of the fungicidal composition of claim 7 applied to a crop or a growing medium or locus of a crop.
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