CN114621280A - Silicon acrylonitrile compound and preparation method and application thereof - Google Patents
Silicon acrylonitrile compound and preparation method and application thereof Download PDFInfo
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- CN114621280A CN114621280A CN202011460379.6A CN202011460379A CN114621280A CN 114621280 A CN114621280 A CN 114621280A CN 202011460379 A CN202011460379 A CN 202011460379A CN 114621280 A CN114621280 A CN 114621280A
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- -1 Silicon acrylonitrile compound Chemical class 0.000 title claims abstract description 105
- 238000002360 preparation method Methods 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 239000000203 mixture Substances 0.000 claims abstract description 56
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 18
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 16
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 238000006467 substitution reaction Methods 0.000 claims description 35
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 25
- 239000000651 prodrug Substances 0.000 claims description 24
- 229940002612 prodrug Drugs 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 241000238876 Acari Species 0.000 claims description 20
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 19
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 18
- 241000196324 Embryophyta Species 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 241000238631 Hexapoda Species 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 241000221785 Erysiphales Species 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 230000000844 anti-bacterial effect Effects 0.000 claims description 11
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 241000254173 Coleoptera Species 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 241000258937 Hemiptera Species 0.000 claims description 9
- 241000233639 Pythium Species 0.000 claims description 9
- 241000607479 Yersinia pestis Species 0.000 claims description 9
- 241000257303 Hymenoptera Species 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
- 241000894006 Bacteria Species 0.000 claims description 7
- 241001361634 Rhizoctonia Species 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 claims description 6
- 241000256602 Isoptera Species 0.000 claims description 6
- 241000238814 Orthoptera Species 0.000 claims description 6
- 241001414989 Thysanoptera Species 0.000 claims description 6
- 235000013601 eggs Nutrition 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 241001674044 Blattodea Species 0.000 claims description 5
- 229940126062 Compound A Drugs 0.000 claims description 5
- 241000255925 Diptera Species 0.000 claims description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 5
- 241000255777 Lepidoptera Species 0.000 claims description 5
- 241000244206 Nematoda Species 0.000 claims description 5
- 241000258242 Siphonaptera Species 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
- 241000918585 Pythium aphanidermatum Species 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 230000003071 parasitic effect Effects 0.000 claims description 4
- 241001530056 Athelia rolfsii Species 0.000 claims description 3
- 241000228347 Monascus <ascomycete fungus> Species 0.000 claims description 3
- 241001281802 Pseudoperonospora Species 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 241000199919 Phaeophyceae Species 0.000 claims description 2
- 241000221662 Sclerotinia Species 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 241000254234 Xyeloidea Species 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 147
- 238000006243 chemical reaction Methods 0.000 description 86
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 150000003254 radicals Chemical class 0.000 description 63
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 45
- 239000002904 solvent Substances 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 241000256248 Spodoptera Species 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 33
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 238000005406 washing Methods 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 229910000104 sodium hydride Inorganic materials 0.000 description 20
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
- 238000004440 column chromatography Methods 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 241001600407 Aphis <genus> Species 0.000 description 15
- 241000123222 Hericium Species 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- UIAGMCDKSXEBJQ-UHFFFAOYSA-N nimodipine Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 241001235638 Chrysomeloidea Species 0.000 description 12
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 241000223238 Trichophyton Species 0.000 description 12
- APJLTUBHYCOZJI-VZCXRCSSSA-N cyenopyrafen Chemical compound CC1=NN(C)C(\C(OC(=O)C(C)(C)C)=C(/C#N)C=2C=CC(=CC=2)C(C)(C)C)=C1C APJLTUBHYCOZJI-VZCXRCSSSA-N 0.000 description 12
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 11
- 241001454293 Tetranychus urticae Species 0.000 description 11
- 241000209140 Triticum Species 0.000 description 11
- 235000021307 Triticum Nutrition 0.000 description 11
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 10
- 241000500437 Plutella xylostella Species 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 244000052616 bacterial pathogen Species 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 241000604373 Ovatus Species 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- BQLMZZVRHPZRBQ-UHFFFAOYSA-N ethyl 2-(trifluoromethyl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1C(F)(F)F BQLMZZVRHPZRBQ-UHFFFAOYSA-N 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 239000000575 pesticide Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000010791 quenching Methods 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
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- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- JAVLKNNRYBFEGM-UHFFFAOYSA-N 2-phenyl-2-trimethylsilylacetonitrile Chemical compound C[Si](C)(C)C(C#N)C1=CC=CC=C1 JAVLKNNRYBFEGM-UHFFFAOYSA-N 0.000 description 5
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- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
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- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 5
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- WUUUUWIHHKLIHO-UHFFFAOYSA-N ethyl 2,4,5-trimethylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=C(C)C(C)=NN1C WUUUUWIHHKLIHO-UHFFFAOYSA-N 0.000 description 5
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
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- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- HAXSCOGBPLMKKV-UHFFFAOYSA-N benzene;1h-indole Chemical group C1=CC=CC=C1.C1=CC=C2NC=CC2=C1 HAXSCOGBPLMKKV-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229940075397 calomel Drugs 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000008199 coating composition 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
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 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
- 229940043279 diisopropylamine Drugs 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- QOUFDDUDXYJWHV-UHFFFAOYSA-N ethyl 2-iodobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1I QOUFDDUDXYJWHV-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 235000002532 grape seed extract Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 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
- 150000002576 ketones Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 208000028454 lice infestation Diseases 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P5/00—Nematocides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/02—Acaricides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Insects & Arthropods (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a silicon acrylonitrile compound and a preparation method and application thereof. In particular to a compound shown as a formula I, a composition containing the compound shown as the formula I and application of the compound and the composition. The compounds of the present invention have excellent acaricidal, insecticidal and fungicidal activity.
Description
Technical Field
The invention belongs to the field of agricultural pharmacy, and particularly relates to a silicon acrylonitrile compound and a preparation method and application thereof.
Background
Harmful mites, insects and crop pathogenic bacteria often cause great loss to economic crops such as grains, vegetables, fruits, cotton, ornamental plants and the like, and the prevention and control of the harmful mites, the insects and the crop pathogenic bacteria by utilizing chemical acaricides, insecticides and bactericides is vital to ensuring the safety of the economic crops and improving the living standard of people. As a large country of pesticide, China has huge dosage of chemical acaricide, insecticide and bactericide, has wide market prospect and has vigorous demand for new products. However, with the long-term use of large quantities of harmful mites, insects and pathogenic bacteria, the harmful mites, insects and pathogenic bacteria have already developed serious resistance to the existing agricultural protective agents, and the ecological safety problem of the existing pesticides is increasingly highlighted.
Although acrylonitrile compounds having acaricidal, insecticidal and/or fungicidal activities have been disclosed in the prior art, these compounds have problems of serious structural homogeneity, outstanding resistance to pests and the like, and the research progress of novel acaricides has been slow. Therefore, the temperature of the molten metal is controlled,
in view of the above, there is an urgent need in the art to develop a new class of compounds having excellent insecticidal and acaricidal activity.
Disclosure of Invention
The invention aims to provide a silicon acrylonitrile compound with excellent acaricidal, insecticidal and bactericidal activities, novel structure, excellent effect and less toxic and side effects.
In a first aspect of the invention, there is provided a compound of formula I, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof,
in the formula (I), the compound is shown in the specification,
R1selected from the group consisting of substituted or unsubstituted: c1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C3-6Cycloalkoxy, C1-6Alkylthio radical, C3-6Cycloalkylthio radical, C6-C10Aryl, 5-10 membered heteroaryl, 4-10 membered heterocyclyl; wherein said substitution is by one or more RaSubstitution;
R2、R3and R4Each independently selected from the group consisting of substituted or unsubstituted: hydrogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6An alkynyl group; wherein said substitution is by one or more RaSubstitution;
or, R2And R3、R3And R4Or R2And R4Together form a group selected from: - (CH)2)p-、-(CH2)o-O-(CH2)p-O-(CH2)o-; wherein o is independently 0, 1, 2, 3, or 4, and p is 2, 3,4, 5, or 6;
R5selected from the group consisting of substituted or unsubstituted: c1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C3-6Cycloalkylthio radical, R6And R7(ii) a Wherein said substitution is by one or more RaSubstitution;
R6is substituted or unsubstituted C6-14An aryl group; r is6Wherein said substitution means that the hydrogen on the group is substituted with 1 to 5 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C3-6Cycloalkylthio, -CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;
R7Is unsubstituted or substituted 5-14 membered heteroaryl; r7Wherein said substitution means that the hydrogen on the group is substituted with 1 to 5 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C3-6Cycloalkylthio, -CN, NO2、SO2R8、COR8、COOR8、CONR8R9And SO2NR8R9;
R8And R9Each independently selected from the group consisting of substituted or unsubstituted: hydrogen, C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl, C6-14Aryl, 5-14 membered heteroaryl; or, R8And R9Taken together with the N atom to which they are attached form a substituted or unsubstituted 3-6 membered heterocyclyl; wherein said substitution is by one or more RaSubstitution;
each X is independently selected from the group consisting of: hydrogen, halogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6Alkyl, halo C1-6Alkoxy, -CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;
Z is selected from: CRbRcOxygen, sulfur or NRd;
(CH2)nH in (1) may be substituted by RaSubstitution;
or Z- (CH)2)n-R1The moiety is selected from the group consisting of substituted or unsubstituted: c1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl, C6-14Aryl, 5-14 membered heteroaryl; wherein said substitution is by one or more RaSubstitution;
Rb、Rceach is independentThe land is selected from the following group: hydrogen, halogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6Alkyl, halo C1-6Alkoxy, -CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;
RdSelected from the group consisting of: hydrogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6An alkyl group;
Raselected from the group consisting of: hydrogen, halogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6Alkyl, halo C1-6Alkoxy, -CN, -NO2Oxo, C3-6Cycloalkyl, 3-6 membered heterocyclyl, -SO2R10、-COR10、-COOR10、-CONR10R11and-SO2NR10R11(ii) a Wherein R is10、R11Each independently selected from the group consisting of: hydrogen, C1-6Alkyl, halo C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl, C6-14Aryl, 5-14 membered heteroaryl;
m is 0, 1, 2, 3 or 4; n is 0, 1, 2, 3 or 4.
In another preferred embodiment, R1Selected from the group consisting of: c1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C3-6Cycloalkoxy, C1-6Alkylthio radical, C3-6Cycloalkylthio, phenyl, 4-10 membered heterocyclyl.
In another preferred embodiment, R5Selected from the group consisting of substituted or unsubstituted: c6-14Aryl and 5-14 membered heteroaryl, wherein said substitution means that the hydrogen on the group is substituted by 1-5 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C3-6Cycloalkylthio, -CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9(ii) a Wherein R is8And R9Each independently selected from the group consisting of: hydrogen, C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl.
In another preferred embodiment, R7Is a group selected from the group consisting of substituted or unsubstituted: thiazolyl, thiadiazolyl, isothiazolyl, tetrazolyl, pyridyl, thiomorpholine-S-oxide, thiomorpholine-S, S-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, oxazolyl, oxadiazolyl, isoxazolyl, furanyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl; r7Wherein said substitution means that the hydrogen on the group is substituted with 1 to 4 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C1-6Alkylthio of, C3-6Cycloalkylthio, CN, NO2、SO2R8、COR8、COOR8、CONR8R9And SO2NR8R9;R8And R9Each independently selected from the group consisting of: hydrogen, C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl.
In another preferred embodiment, the compound of formula I, its geometric isomer, stereoisomer, or an agriculturally pharmaceutically acceptable salt or prodrug thereof, has the structure shown in formula II or formula III
In the formula, X, m, R1、R2、R3、R4、R5Z and n are as defined above.
In another preferred embodiment, the compounds of formula I, their geometric isomers, stereoisomers, or agriculturally and pharmaceutically acceptable salts or prodrugs thereof,R5Selected from the group consisting of substituted or unsubstituted: phenyl, naphthyl, thiazolyl, thiadiazolyl, isothiazolyl, tetrazolyl, pyridyl, thiomorpholine-S-oxide, thiomorpholine-S, S-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, oxazolyl, oxadiazolyl, isoxazolyl, furanyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl; wherein said substitution is such that the hydrogen on the group is substituted by 1 to 5 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C1-6Alkylthio of, C3-6Cycloalkylthio, CN, NO2、SO2R8、COR8、COOR8、CONR8R9And SO2NR8R9;R8And R9Each independently selected from the group consisting of: hydrogen, C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl.
In another preferred embodiment, the compound of formula I, a geometric isomer, a stereoisomer, or an agriculturally pharmaceutically acceptable salt or prodrug thereof, R5Selected from the group consisting of:
in the formula (I), the compound is shown in the specification,
g is independently 0, 1, 2, 3,4 or 5;
each R' is independently selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C1-6Alkylthio of, C3-6Cycloalkylthio, CN, NO2、SO2R8、COR8、COOR8、CONR8R9And SO2NR8R9;R8And R9Each independently selected from the group consisting of: hydrogen, C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl.
In another preferred embodiment, the compound of formula I, a geometric isomer, a stereoisomer, or an agriculturally pharmaceutically acceptable salt or prodrug thereof, R5Selected from the group consisting of:
in another preferred embodiment, the compound of formula I, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof, (CH)2)n-R1The moiety is selected from the group consisting of substituted or unsubstituted: H. c1-6Alkyl radical, C2-4Alkenyl radical, C2-4Alkynyl, C1-6Alkylthio radical, C1-6Alkoxy, 3-6 membered cycloalkyl, C6-C10Aryl, 5-10 membered heteroaryl, 4-10 membered heterocyclyl, (CH)2) R ', R' is selected from: 3-6 membered cycloalkyl, C6-C10Aryl, 5-10 membered heteroaryl, 4-10 membered heterocyclyl; wherein said substitution is by one or more groups selected from the group consisting of: c1-6Alkyl radical, C1-6Alkoxy radical, C1-6Alkylthio, -CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;R8And R9Each independently selected from the group consisting of: hydrogen, C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl.
In another preferred embodiment, the compound of formula I, a geometric isomer, a stereoisomer, or an agriculturally pharmaceutically acceptable salt or prodrug thereof, R2、R3And R4Each independently selected from the group consisting of: c1-6Alkyl radical, C2-4Alkenyl and C2-4Alkynyl.
In another preferred embodiment, the compound of formula I, a geometric isomer, a stereoisomer, or an agriculturally pharmaceutically acceptable salt or prodrug thereof, has the structure shown in formulas I-xvi
In the formula (I), the compound is shown in the specification,
R1、R2、R3、R4x, m, n, Z are as defined above.
In another preferred embodiment, the compound of formula i-xvi, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof, R1、R2、R3、R4X, m, n, Z have the definitions shown in Table a
TABLE a
In another preferred embodiment, the compound is selected from the compounds shown in the examples.
In a second aspect of the present invention, there is provided a process for the preparation of a compound of the first aspect, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof, said process comprising the steps of:
wherein, m, n, R1、R2、R3、R4、R5X and Z are as defined above;
(s1) reacting compound A with compound B in an inert solvent in the presence of a base to give the compound of formula I.
In another preferred embodiment, the process for preparing the compound of formula I further comprises the steps of:
wherein, m, n, R1、R2、R3、R4、R5And X is as defined above;
(s0) reacting compound C with compound D in an inert solvent in the presence of a catalyst to obtain compound A.
In another preferred embodiment, step (s1) is: reacting a compound of formula a and a compound of formula B in a solvent (preferably selected from benzene, toluene, ethyl acetate, acetonitrile, dichloromethane, dichloroethane, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, 1, 4-dioxane, PEG400, n-heptane, n-hexane, cyclohexane, petroleum ether, dimethylformamide, dimethylsulfoxide, or a combination thereof) in the presence of a base (preferably selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium hydride, sodium methoxide, sodium ethoxide, triethylamine, dimethylaminopyridine, sodium tert-butoxide, potassium tert-butoxide, lithium diisopropylamide, diisopropylethylamine, pyridine, or a combination thereof) at 0-25 ℃ or 0 ℃ to reflux temperature to obtain a compound of formula I.
In another preferred embodiment, step (ii) (i.e., the reaction shown in equation 2) is: reacting a compound of formula C with a compound of formula D in the presence of a base (preferably, the base is selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, sodium methoxide, sodium ethoxide, triethylamine, dimethylaminopyridine, sodium tert-butoxide, potassium tert-butoxide, lithium diisopropylamide, diisopropylethylamine, pyridine, or combinations thereof) at 0-25 ℃ or 0 ℃ to reflux temperature in a solvent (preferably, the solvent is selected from benzene, toluene, ethyl acetate, acetonitrile, ethylene glycol monomethyl ether, dichloromethane, dichloroethane, tert-butanol, 1, 4-dioxane, n-butanol, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, n-heptane, n-hexane, cyclohexane, petroleum ether, dimethylformamide, dimethylsulfoxide, or combinations thereof) to obtain a compound of formula a.
In a third aspect of the invention, there is provided a use of a compound according to the first aspect, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof,
(i) useful for killing and/or controlling at least one pest from the orders Acarina, Symphenoptera, Orthoptera, Blattaria, Isoptera, Anoploptera, Thysanoptera, Heteroptera, Homoptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Siphonaptera and plant parasitic nematodes and/or their nymphs and/or their eggs;
(ii) can be used for preventing and treating at least one plant disease of anthracnose, leaf spot, rust disease, powdery mildew, banded sclerotial blight, leaf blight, gray mold, southern blight, damping off, gibberellic disease, full rot and target spot caused by infection of rhizoctonia, sclerotinia, pseudoperonospora, monascus, phaeophyceae, pythium and the like;
(iii) for the preparation of a composition or formulation for killing and/or controlling mites and/or their eggs;
(iv) for insecticidal and/or bactericidal use; and/or
(v) For the production of compositions or preparations for acaricidal and/or insecticidal and/or fungicidal use.
In another preferred embodiment, the compounds of the formula I are used for combating and/or controlling mites and/or for preparing compositions or preparations for combating pests and/or killing bacteria.
In another preferred embodiment, the compounds of the formula I are used for combating and/or controlling harmful acarids and/or their eggs in agriculture, in pastures, on lawns and/or indoors.
In another preferred embodiment, the compounds of the formula I are used for combating and/or controlling pests and/or bacteria in agriculture, in pastures, on lawns and/or indoors.
In another preferred embodiment, the mites are harmful mites.
In another preferred embodiment, the mites are selected from the group consisting of: tetranychus urticae (Tetranychus urticae Koch), Tetranychus urticae (Tetranychus viennensis Zacher), Tetranychus truncatus (Tetranychus truncatus Ehara), Tetranychus cinnabarinus (Tetranychus cinnabarinus Boisdruval), Panonychus ulmi (Panychus ulmi Koch), Panonychus citri (Panychus citri McGregor), Carex orchidus (Bryobia rubrus Scheuten), Trionycis tritici (Petrobia latifolia Muller), Tetranychus brachypus (Oligonchus uneguensis Jacobius), Brevibacterium ovatus (Brevitus ovatus Donnadei), and Brevibacterium flavus (B. leii McGregor), oriental peach blossom mites (Tenuipipus taonicas Ma et Yuan), Diospyros kaki Thunb (Tenuipipus zhizhizhi huas Viliae Reck), vitis vinifera Hemsl (C. vitas Pagentecher), Steinwedeli Keifer (A. stepwedeli Keifer), Lycium chinense Purpus (A. macroodonis Keifer), Pyricularia pyrifolia (Eriophenous pyrus Pagent), Ruscus aculeatus (Epitrimerus pirifolia Keifer), Tarsonemus laterosomus (Polyphalaovorus lateus Linnaeus Banks), Tridax merus (Penthanus major Duges), and Rhizopyrus taro (Rhizogylus calcoactus caerutemens).
In another preferred embodiment, the pests are selected from: white pine (Scutigerella immaculata), cricket (Acheta domestica), Gryllotalpa (Gryllotalpa sp.), African migratory locust (Locusta inigera), Black locust (Melanoplus spp.), desert locust (Schistocher cagregaria), oriental cockroach (Blatta orientalis), American cockroach (Periplaneta), Florida (Leucopia amadorae), German cockroach (Blattella gernanica), Anthrix (Reticuloruliginis spp.), Pediculus humanus (Pediculus hunculus), Haematophagus (Haematophagus spp.), Phthirius (Linognatus spp.), Phthirius (Trichophyton trichia, Triplophyta (Trichophyton), Triplophyta (Trichophyton trichopterus), Triplophyta (Trichophyton trichopteris), Triplophyta (Trichophyton trichophyta), Thraustria spp), Thrombus (Trichophyton trichophyta), Thraustria spp (Trichophyton trichophyta), Trichophyton trichophyta (Trichophyton, Thraustria spp), Thraustria spp (Trichophyton trichophyta), Periplus spp), Periplaneta (Trichophyta trichophyta (Herpyris), Periplaneta (Herpyris), Periplaneta (Herpyris (Hericium spp), Periplaneta (Hericium falciparum spp), Periplaneta (Hericium falcatus spp), Periplaneta (Hericium falcatum spp), Periplum falcatum spp (Hericium spp), Periplum falcatum spp (Hericium falcatum spp), Periplum spp (Hericium falcatum spp (Thunbergii (Hericium spp), Periplum spp (Hericium spp), Periplum falcatum spp (Hericium spp), Periplum spp (Thunberg (Hericium spp), Periplum spp (Frankinium spp), Periplum spp (Hericium spp), Periplum spp (Thunbergii (Frankinium spp), Periplum spp (Frankinium spp), Periplum falcatum spp), Periple (Hericium spp (Herpyritum (Hericium spp), Periple (Herpyritum (Thunberg (Herpyri (Hericium spp), Periple (Herpyritum (Herpyri (Thunberg (Herpyri) and Periplum spp), Haplophorum spp), Periplum spp), Periple (Mipalum spp), Periplum spp), Periple (Herpyri (Haplophorum spp), Periplum spp), Periple (Herpyri (Herpyritum (Herpyri, Whitefly (Aleurodeses brasticae), powdered tobacco (Beirisia tabaci), Trialeurodes grisea (Trialeurodes vaporariorum), Aphis gossypii (Aphis gossypii), Aphis brassicae (Brevicornus brassiccus), Aphis virginiana (Cryptomyces striatus), Aphis nigricans (Aphis fabae), Aphis citrina (Aphis flavus), Aphis pomorum (Eriosoma lanigerum), Aphis metformis (Hyalophorus grandiflorus), Aphis viticola (Phyllotreta), Aphis gossypii (Perothrix), Aphis graminicola (Phyllocerulosa), Aphis gramineus (Phyllocerulosa), Phyllocerulosa viridiplus viridans (Pholiota), Phyllocercus nigra, Phyllocerulosa viridans (Pholiota), Phyllocercus carotovorax (Pholiota), Phyllocerus spp), Phyllocercospora (Pholiota), Phyllocercospora viridae (Leporus), Phyllocerotis spp), Phyllochavicia viridae (Leporus spp), Phyllochaetes spp), Phyllochavicia viride (Leporus spp), Phyllochavicia spp (Leporus spp), Phyllochavicia spp (Pyrus spp), Phyllochavicia spp (Pholiota), Phyllochavicia spp (Leporus spp (Pyrus spp), Phyllochavicia spp (Nephophora, Phyllochavicia spp), and Myospiriella spp (Nephophora spp), Phyllochavicia spp) Red bell wheat moth (Petrophora gossypiella), looper (Bupalus piniarius), winter striped moth (Cheirnathia braunia), apple moth (Lithocolletis blancardella), apple moth (Hypomelia padella), cabbage moth (Plutella xylostella), yellow brown tenella ((Malacola neostia), yellow moth (Euproctitis chrysomyrea), moth (Lyinantia spp.), cotton sneaker (Bucclusix thyteriella), orange sneaker (Phycrythris ostreatus), cutworm (Eudragia sp.), Spoloptera Spodoptera, Spodoptera, Spodoptera (Spodoptera), Spodoptera frugiperda (Spodoptera), Spodoptera) Spodoptera (Spodoptera), Spodoptera (Spodoptera), Spodoptera (Spodoptera) Spodoptera, Spodoptera (Spodoptera) Spodoptera, Spodoptera (Spodoptera, Spodoptera (Spodoptera) and Spodoptera) Spodoptera (Spodoptera, Spodoptera (Spodoptera) and Spodoptera) Spodoptera (Spodoptera) Spodoptera, Spodoptera (Spodoptera) Spodoptera, Spodoptera (Spodoptera) of Spodoptera, Spodopter, Corn borer (Pyrausta nubilalis), mediterranean meal borer (Ephestia kuehniella), pyralida (Galleria mellonella), avenae sinensis (Tineola bisselella), Botrytis cinerea (Tineola pellionella), Botrytis cinerea (Men pellionella), Bombycis fulva (Hofrna nigrospora septemella), Sphaeria linonella (Cacoecia podana), Sphaeria punctata (Choristoneura fulica), Botrytis cinerea (Clysidia albuginella), Sphaeria virescens (Homona rnana), Pieris virescens (Todara virida), Philasia punctifera (Cnaphalocrocis), Photinus pyralis (Cnaphalocrocis niponensis), Sphaeria serotina (Photinus), Sphaemaphila palea (Photinus), Sphaemaphila (Pieris terrestris indica), Sphaemaphila (Pieris), Piper falva (Piper) and Sphaemaphysalis (Piper, Sphaemaphysalis), Sphaemaphila (Piper spp), Sphaemaphysalis (Photinus sp) Goodynia mangostana (Oryzaphidia suta), Ceratophylla spp (Anthonomus spp.), Rhynchophylla (Sitophilus spp.), Aleuryphylus nigratus (Oclernchus Sulcatus), Scyphylla sativa (Cosinopoloides sondus sordidus), Ceratophylla brassicae (Ceratophyllus assiliensis), Ceratophyllus purpureus (Hypera pottica), Sclerotis (Desmesspps spp.), Rhynchophorus maculatus (Trogopterus spp.), Rhynchophorus orbiculatus ((Anthronus spp.), bark beetle pis (Atlantana spp.), Ceratopterus (Atgenophycus spp.), Ceratophyllus (Lyctus spp.), Ceratophyllum spicatula (Meyloides), Ceratophyllopodium purpurea spica (Melothuropterocarpus spp.), Melothria spp.), Melothrix (Melothrix spp.), Melothrix Spiropsis spp.), Melothrix (Melothrix spp.), Melothrix Spirosporum (Melothrix spp.), Melothrix spp (Melothrix spp.), Melothrix spp. (Melothrix spp.), or Melothrix spp (Melothrix spp.), Melothrix spp (Melothrix spp.), Melothrix spp (Melothrix spp), Melothrix spp. sp. sp.sp. sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.P (Melothrix), Melothrix spp.), and Melothrix spp.), or Melothrix spp. (Melothrix spp.), Melothrix spp. (Melothrix spp.), or Melothrix spp. sp.sp.sp.sp.albus (Melothrix spp.), or Melothrix spp. sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.sp.T.sp.sp.sp.sp.sp.sp.sp.sp.sp., The genus Trichophyton ((Dipnion spp.), Ceratoptera (Hoplocpap spp.), the genus Trichophyton (Lasius spp.), the genus Microptera (Monononium pharaonis), the genus Vespa (Vespa spp.), the genus Aedes (Aedes spp.), the genus Anopheles (Anopheles spp.), the genus Culex (Culex spp.), the genus Drosophila melanogaster (Drosophila melanogaster), the genus Musca spp.), the genus Fannia spp, the genus Rhododendron virginalis (Callica), the genus Lucilia (Lucilia spp.), the genus Chrysomyzilla (Chrysomyia spp.), the genus Flabellosa (Cuebra spp.), the genus Gastrophania (Phymatopsis spp.), the genus Paralichia (Ostreta), the genus Paralichia (Phormidis), the genus Paralichia spp.), the genus Paralichia (Ostrex spp.), the genus Ostreta (Ostrematophagia spp.), the genus Paralichia (Phormidis), the genus Paralichia spp.), the genus Ostrex spp.), the genus Chrysomyia (Ostrematodinia spp.), the genus Chrysomyia (Ostrex spp.), the genus Paralichia spp.), the genus Ostrematodinia (Pholidocarpa, the genus Paralichia (Pholidae (Phormidis), the genus Ostrex spp.), the genus Paralichia spp.), the genus Paralichia (Phormidis), the genus Paralichia (Pilatus spp.), the genus Paralichia (Pikeramis (Pilatus (Pikeramis (Pilatus spp.), the genus Pikeramis (Pilatus (Pilat) and the genus, the genus Pikeramis (Pilat) of the genus, the genus of the genus Pikeramis (Pikeramis), the genus Pikeramis (Pikermasia (Pikeramis) of the genus Pikeramis (Pikeramis), the genus Pikeramis (Pikeramis), the genus Pilat), the genus Pikeramis (Pilatus (Pikeramis), the genus Pikeramis (Pikeramis), the genus Pikersfor the genus Pikeramis), the genus Pikeramis (Pikeramis) of the genus Pikeramis (Pikersfor the genus, the genus Pikeramis), the genus Pikersfor the genus Pikeramis (Pilat) of the genus Pilat), the genus Pikeramis (Pikersf, The species bactrocera olivaceus (Dacus oleae), the species aedes europe (Tipula paludosa), the genus melanophora (hylemia spp.), the species bactrocera maculata (Liriotnyza spp.), the species xenorhabdus volvatus (Xenopsylla cheopis), the species ceratophus (Ceratophyllus spp.), the species Pratylenchus spp, the species nematodiasis (Radopholus spp.), the species setaria ciliata (Ditylenchus difolia, Ditylenchus semipenetrans), the species xenorhabdus (tylenchus spp.), the species Heterodera (Heterodera spp.), the species Heterodera globosa (Globodera spp.), the species Meloidogyne spp.), the species setaria spp (melodiophora spp.), the species carotojejunipes spp, the species carotovorax spp (trichoderma spp.), the species nematodia (trichoderma spp.), the species trichoderma spp.).
In another preferred embodiment, examples of the plant having the plant disease include soybean, corn, wheat, melon, rice, strawberry, peanut, cotton; examples of the plant diseases include soybean rust, corn rust, wheat powdery mildew, melon powdery mildew, rice sheath blight, wheat sharp eyespot, strawberry gray mold, peanut southern blight, cotton rhizoctonia rot, wheat scab, wheat take all and cucumber target spot, wherein the melon powdery mildew includes cucumber powdery mildew and the like; the pathogenic bacteria include Phakopsora pachyrhizi (Phakopsora pachyrhizi system.), Puccinia zeae (Puccinia sorghi Schw), Erysiphe necator (Blumeria graminis), Erysiphe cucurbitaceae (Erysiphe cucurbita), Erysiphe cucurbitae (Sphaerotheca cucurbitae), dermataceae (thanatephora cuscutaris), rhizoctonia graminis (rhizoctonia solani), and rhizoctonia solani (rhizoctonia solani), Botrytis cinerea (Botrytis cinerea per), Fusarium graminearum (Fusarium graminearum Schw.), Fusarium avenae (Fusarium avenaceum), moniliforme (Fusarium moniliforme), pythomonas oryzae (phomophilus), Pythium purpurea (phoma niponicum). Preferably the plant disease is caused by rust pseudomonas fabae, phytophthora capsici, pythium and the like.
In a fourth aspect of the present invention, there is provided a composition comprising (i) as active ingredient a compound according to the first aspect, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof; and (ii) a carrier and/or surfactant.
In another preferred embodiment, the compound is present in the composition in an amount of 0.001 to 99.999 wt%.
In another preferred embodiment, the composition is a pesticide composition; preferably, the composition is a miticidal composition, an insecticidal composition and a bactericidal composition.
In a fifth aspect of the present invention, there is provided a method of killing mites, insects and/or bacteria, comprising the steps of: contacting the mites, insects and/or bacteria with an effective amount of a compound as described in the first aspect, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof or a composition as described in the fourth aspect.
It is to be understood that within the scope of the present invention, the above-described features of the present invention and those specifically described below (e.g., in the examples) may be combined with each other to form new or preferred embodiments. Not to be reiterated herein, but to the extent of space.
Drawings
Is free of
Detailed Description
The inventors have extensively and intensively studied and unexpectedly found a class of silicon-containing acrylonitrile-based compounds (represented by formula I) having a novel structure, which have excellent acaricidal and/or insecticidal and/or fungicidal activities. Based on this, the inventors have completed the present invention.
Term(s) for
As used herein, the term "halogen" refers to fluorine, chlorine, bromine or iodine.
Unless otherwise defined, the term "alkyl" by itself or as part of another substituent refers to a straight or branched chain hydrocarbon radical having the indicated number of carbon atoms (i.e., C)1-6Representing 1-6 carbons). Examples of alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, isobutyl, sec-butyl, n-pentyl, n-hexyl, and the like.
Unless otherwise indicated, the term "alkenyl" refers to an unsaturated alkyl group having one or more double bonds. Similarly, the term "alkynyl" refers to an unsaturated alkyl group having one or more triple bonds. Examples of such unsaturated alkyl groups include ethenyl, 2-propenyl, crotyl, 2-isopentenyl, 2- (butadienyl), 2, 4-pentadienyl, 3- (1, 4-pentadienyl), ethynyl, 1-and 3-propynyl, 3-butynyl, and higher homologs and isomers.
Unless otherwise defined, the term "cycloalkyl" refers to a ring having the indicated number of ring atoms (e.g., C)3-6Cycloalkyl) saturated or unsaturated cyclic hydrocarbon groups. Examples of such cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and the like.
Unless otherwise indicated, the term "aryl" denotes a polyunsaturated (usually aromatic) hydrocarbon group which may be a single ring or multiple rings (up to three rings) which are fused together or linked covalently. Examples of aryl groups include: a phenyl group.
Unless otherwise defined, the term "heterocycloalkyl" or "heterocyclyl" refers to a cycloalkyl group containing one to five heteroatoms selected from N, O and S, wherein the nitrogen and sulfur atoms are optionally oxidized, and the nitrogen atom is optionally quaternized. The heterocycloalkyl group can be a monocyclic, bicyclic, or polycyclic ring system. Non-limiting examples of heterocycloalkyl groups include pyrrolidine, imidazolidine, pyrazolidine, butyrolactam, valerolactam, imidazolidinone, hydantoin, dioxolane, phthalimide, piperidine, 1, 4-dioxane, morpholine, thiomorpholine-S-oxide, thiomorpholine-S, S-oxide, piperazine, pyran, pyridone, 3-pyrroline, thiopyran, pyrone, tetrahydrofuran, tetrahydrothiophene, quinuclidine, and the like. The heterocycloalkyl group can be attached to the rest of the molecule via a ring carbon or a heteroatom. By terms such as cycloalkylalkyl and heterocycloalkylalkyl, it is meant that the cycloalkyl or heterocyclyl group is attached to the remainder of the molecule through an alkyl or alkylene linker.
Unless otherwise defined, the term "heteroaryl" refers to an aryl (or ring) containing 1 to 5 heteroatoms selected from N, O, and S, wherein the nitrogen and sulfur atoms are optionally oxidized and the nitrogen atoms are optionally quaternized. The heteroaryl group may be attached to the rest of the molecule through a heteroatom. Non-limiting examples of heteroaryl groups include pyridyl, pyridazinyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, benzotriazinyl (benzotriazinyl), purinyl, benzimidazolyl, benzpyrazolyl, benzotriazolyl, benzisoxazolyl, isobenzofuranyl, isoindolyl, indolizinyl, benzotriazinyl, thienopyridyl, thienopyrimidinyl, pyrazolopyrimidyl, imidazopyridine, benzothiazolyl, benzofuranyl, benzothienyl, indolyl, quinolinyl, isoquinolinyl, isothiazolyl, pyrazolyl, indazolyl, pteridinyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiadiazolyl, pyrrolyl, thiazolyl, furanyl, thienyl, and the like.
As used herein, the term "heteroatom" is meant to include oxygen (O), nitrogen (N), sulfur (S), and silicon (Si).
For the compounds provided herein, a bond from a substituent (typically an R group) to the center of an aromatic ring (e.g., benzene, pyridine, etc.) will be understood to refer to a bond that provides attachment at any available vertex of the aromatic ring. In some embodiments, the description also includes a link on a ring fused to the aromatic ring. For example, a bond drawn to the center of the indole benzene moiety would represent a bond to any available vertex of the six or five membered ring portion of the indole.
As used herein, the terms "comprising," "including," or "including" mean that the various ingredients may be used together in a mixture or composition of the invention. Thus, the terms "consisting essentially of and" consisting of are encompassed by the term "comprising.
Unless otherwise specified, the compounds of formula I of the present invention include geometric isomers (Z and E represent different configurations, respectively) that may be formed due to the attachment of different substituents to a carbon-carbon double bond or a carbon-nitrogen double bond, and the present invention includes Z-type and E-type isomers and mixtures thereof in any proportion. The compound shown in the formula I comprises stereoisomers (R and S respectively represent different configurations) which can be formed by connecting different substituents on a carbon-nitrogen atom, and the invention comprises R-type isomers, S-type isomers and mixtures thereof in any proportion. The compound shown in the formula I of the invention not only comprises geometric isomers (Z/E formula) and stereoisomers (R/S formula), but also comprises a mixture of the geometric isomers and the stereoisomers in any proportion.
As used herein, "effective amount" refers to: the amount of the compound is enough to produce the effect of killing mites, insects and bacteria without causing serious negative effects.
As used herein, for example, "1 to 5" means 1, 2, 3,4, or 5, and "1-10" means 1, 2, 3,4, 5, 6, 7, 8, 9, or 10.
Silicon-containing acrylonitrile compound
As used herein, the term compound of the present invention refers to a class of silacrylonitrile compounds represented by formula I, which term also includes geometric isomers, or stereoisomers thereof, or salts, or mixtures of isomers thereof.
Specifically, the invention provides a silicon acrylonitrile compound shown in a formula I,
in the formula I, R1、R2、R3、R4、R5Z, n, X and m are as defined above.
Preferably, the compound has a structure represented by formula II or formula III
X、m、R1、R2、R3、R4、R5Z and n are as defined above.
Preferably, in the formulae I-III, R5Selected from the group consisting of substituted or unsubstituted: phenyl, naphthyl, thiazolyl, thiadiazolyl, isothiazolyl, tetrazolyl, pyridyl, thiomorpholine-S-oxide, thiomorpholine-S, S-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, oxazolyl, oxadiazolyl, isoxazolyl, furanyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl; wherein said substitution is such that the hydrogen on the group is substituted by 1 to 5 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radicals、C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C1-6Alkylthio of, C3-6Cycloalkylthio, CN, NO2、SO2R8、COR8、COOR8、CONR8R9And SO2NR8R9;R8And R9Each independently selected from the group consisting of: hydrogen, C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl.
Preferably, in the formulae I to III, Z- (CH)2)n-R1The moiety is selected from the group consisting of substituted or unsubstituted: c1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl, C6-14Aryl, 5-14 membered heteroaryl, C1-6Alkyl O-, C3-6Cycloalkyl O-, 3-6 membered heterocyclyl O-, C6-14Aryl O-, 5-14 membered heteroaryl O-, C1-6Alkyl radical S-, C3-6Cycloalkyl S-, 3-6 membered heterocyclyl S-, C6-14Aryl S-, 5-14 membered heteroaryl S-, NR8R9;
Wherein R is8And R9Is as defined above.
Preferably, in the formulae I-III, R2、R3And R4Each independently selected from the group consisting of: c1-6Alkyl radical, C2-4Alkenyl and C2-4Alkynyl.
Preferably, in the formulae I-III, R1Selected from the group consisting of: c1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C3-6Cycloalkoxy, C1-6Alkylthio radical, C3-6Cycloalkylthio, phenyl, 4-to 10-membered heterocyclyl.
Preferably, in formula I, R1Selected from the group consisting of: c1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C3-6Cycloalkoxy, C1-6Alkylthio radical, C3-6Cycloalkylthio, phenyl;
n is 0, 1, 2 or 3;
R2、R3and R4Each independently selected from the group consisting of: c1-6Alkyl radical, C2-6Alkenyl radical, C2-6An alkynyl group;
or, R2And R3、R3And R4Or R2And R4Together form- (CH)2)p-a group of (a); wherein p is 2, 3,4, 5, or 6;
R5selected from the group consisting of: r6And R7;
R6Is substituted or unsubstituted phenyl; r6Wherein said substitution means that the hydrogen on the group is substituted by 1, 2 or 3 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C1-6Alkoxy, CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;
R7Is an unsubstituted or substituted radical selected from the group consisting of: thiazolyl, pyridyl, thiomorpholine-S-oxide, thiomorpholine-S, S-oxide, pyridazinyl, pyrazinyl, thienyl, furyl, pyrrolyl, pyrazolyl; r7Wherein said substitution means that the hydrogen on the group is substituted by 1, 2, 3 or 4 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C1-6Alkoxy, CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;
Wherein R is8And R9Each independently selected from: hydrogen, C1-6An alkyl group;
each X is independently selected from the group consisting of: hydrogen, halogen, C1-6An alkyl group;
m is 1 or 2;
z is selected from: CRbRcOxygen, sulfur or NRd;
Or Z- (CH)2)n-R1The moiety is selected from the group consisting of substituted or unsubstituted: c1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl、C6-14Aryl, 5-14 membered heteroaryl, C1-6Alkyl O-, C3-6Cycloalkyl O-, 3-6 membered heterocyclyl O-, C6-14Aryl O-, 5-14 membered heteroaryl O-, C1-6Alkyl radical S-, C3-6Cycloalkyl S-, 3-6 membered heterocyclyl S-, C6-14Aryl S-, 5-14 membered heteroaryl S-, NR8R9;
Rb、RcEach independently selected from the group consisting of: hydrogen, halogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6Alkyl, halo C1-6Alkoxy, -CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;
RdSelected from the group consisting of: hydrogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6An alkyl group;
and R is1、R2、R3、R4、R5、R6、R7、R8、R9And one or more hydrogen atoms in the group X may also each independently be substituted with a substituent selected from the group consisting of: halogen, C1-3Alkyl group of (1).
Preferably, in formula I, R1Selected from the group consisting of: c1-6Alkyl of (C)2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C3-6Alkoxy radical, C3-6Cycloalkoxy, C1-6Alkylthio radical, C3-6Cycloalkylthio, phenyl;
n is 0, 1 or 2;
R2、R3and R4Each independently selected from the group consisting of: c1-6Alkyl radical, C2-4Alkenyl and C2-4Alkynyl;
-SiR2R3R4the substitution site of (b) is 3-or 4-position;
R5is 1,3, 4-trimethylpyrazol-5-yl, 2-trifluoromethyl-phenyl, 2-iodo-phenyl, 2-bromo-phenyl, 5-chloro-1, 3-dimethyl-4-pyrazolyl, 5-fluoro-1, 3-dimethyl-4-pyrazolyl1-methyl-3-trifluoromethyl-4-pyrazolyl, 1-ethyl-3-methyl-5-pyrazolyl, 2-methyl-4-trifluoromethyl-5-thiazolyl, 2-chloro-3-pyridyl, 1,3, 5-trimethylpyrazol-4-yl, 2-trifluoromethyl-3-pyridyl, 2-trifluoromethyl-3-pyrazinyl, 2-methyl-3-furyl, 3-methyl-2-thienyl and 1-methyl-3-difluoromethyl-4-pyrazolyl;
each X is independently selected from the group consisting of: hydrogen, halogen and C1-6An alkyl group;
m is 1 or 2;
z is selected from: CRbRcOxygen, sulfur or NRd;
Or Z- (CH)2)n-R1The moiety is selected from the group consisting of substituted or unsubstituted: c1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl, C6-14Aryl, 5-14 membered heteroaryl, C1-6Alkyl O-, C3-6Cycloalkyl O-, 3-6 membered heterocyclyl O-, C6-14Aryl O-, 5-14 membered heteroaryl O-, C1-6Alkyl radical S-, C3-6Cycloalkyl S-, 3-6 membered heterocyclyl S-, C6-14Aryl S-, 5-14 membered heteroaryl S-, NR8R9;
Rb、RcEach independently selected from the group consisting of: hydrogen, halogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6Alkyl, halo C1-6Alkoxy, -CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;
RdSelected from the group consisting of: hydrogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6An alkyl group;
R8and R9Each independently selected from: hydrogen, C1-6An alkyl group;
and R is1、R2、R3、R4、R5、R6、R7、R8、R9And one or more hydrogen atoms in the group X may also each independently be substituted with a substituent selected from the group consisting of: halogen, C1-3Alkyl group of (1).
Preferably, the compound of formula I has a structure represented by formula I-xvi
In the formula (I), the compound is shown in the specification,
R1、R2、R3、R4x, m, n, Z are as defined above.
Preferably, in the compounds of formula i-xvi, R1、R2、R3、R4X, m, n, Z are as defined in Table a
TABLE a
Process for the preparation of the compounds of the invention
The process for the preparation of the compounds of formula I according to the invention is described in more detail below, but these particular processes do not constitute any limitation of the invention. The compounds of the present invention may also be conveniently prepared by optionally combining various synthetic methods described in the present specification or known in the art, and such combinations may be readily carried out by those skilled in the art to which the present invention pertains.
The present invention also provides a general process for the preparation of a compound according to the first aspect, i.e. a compound of formula I.
Preferably, the method comprises the steps of:
wherein, m, n, R1、R2、R3、R4、R5X and Z are as described above;
(s1) reacting compound A with compound B in an inert solvent in the presence of a base to give the compound of formula I.
In another preferred embodiment, the process for preparing the compound of formula I further comprises the steps of:
wherein, m, n, R1、R2、R3、R4、R5And X is as defined above;
(s0) reacting compound C with compound D in an inert solvent in the presence of a catalyst to obtain compound A.
In another preferred embodiment, step (s1) is: reacting a compound of formula a and a compound of formula B in a solvent (preferably selected from benzene, toluene, ethyl acetate, acetonitrile, dichloromethane, dichloroethane, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, 1, 4-dioxane, PEG400, n-heptane, n-hexane, cyclohexane, petroleum ether, dimethylformamide, dimethylsulfoxide, or a combination thereof) in the presence of a base (preferably selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium hydride, sodium methoxide, sodium ethoxide, triethylamine, dimethylaminopyridine, sodium tert-butoxide, potassium tert-butoxide, lithium diisopropylamide, diisopropylethylamine, pyridine, or a combination thereof) at 0-25 ℃ or 0 ℃ to reflux temperature to obtain a compound of formula I.
In another preferred embodiment, step (ii) (i.e., the reaction shown in equation 2) is: reacting a compound of formula C with a compound of formula D in the presence of a base (preferably, the base is selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, sodium methoxide, sodium ethoxide, triethylamine, dimethylaminopyridine, sodium tert-butoxide, potassium tert-butoxide, lithium diisopropylamide, diisopropylethylamine, pyridine, or combinations thereof) at 0-25 ℃ or 0 ℃ to reflux temperature in a solvent (preferably, the solvent is selected from benzene, toluene, ethyl acetate, acetonitrile, ethylene glycol monomethyl ether, dichloromethane, dichloroethane, tert-butanol, 1, 4-dioxane, n-butanol, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, n-heptane, n-hexane, cyclohexane, petroleum ether, dimethylformamide, dimethylsulfoxide, or combinations thereof) to obtain a compound of formula a.
Combinations comprising the Compounds of the invention and uses of the Compounds of the invention and compositions thereof
The invention also provides a compound shown in the formula I or an agricultural composition containing the silicon acrylonitrile compound shown in the formula I and application thereof.
The silacrylonitrile compound represented by formula I of the present invention shows excellent mite-controlling activity against various pests in agriculture or other fields, particularly spider mites (Arachnida) order (Acarina) mites, such as Tetranychus urticae (Koch), Tetranychus urticae (Zanthopanax vinensis Zacher), Tetranychus truncatus (Tetranychus truncatus Ehara), Tetranychus cinnabarinus (Boisdduval), Tetranychus apple (Panychus ulmi Koch), Tetranychus citrullus (Panychus citri McGregor), Bryomyces bryoides (Bryobia rubrus Scheutenu) Deutus (Bryoides), Triphytes tritici (Petrobius ovatus), Tetranyensis (Tyrophus ovatus), Tetranychii (Tyrophus ovatus), Tetranychus ovatus (Tyrophus ovatus), Tetranychus urticae (Tyrophus ovatus), Lycium chinense (Tyrophus chinensis) Gray, Lycium chinense (Tyropoides), Lycium chinense (Tyrophus chinensis) Gray, et Rust pyricularis (Epitrimerus pirifolia Keifer), Tarsonemus laterospinus (Polygonatum latus Banks), Dermatophagoides meretrix (Penthaleus major Duges), Rhizopus tararicus (Rhizoglyhus calluses Oudemans), and the like. "mite control" means that the mite has acaricidal activity at each stage (egg, larva, adult) of the mite's life cycle. Therefore, the technical scheme of the invention also comprises the application of the silicon acrylonitrile compound shown in the formula I as an acaricide in agriculture or other fields.
The silacrylonitrile compounds of formula I of the present invention are also suitable for controlling at least one pest of the general, orthoptera, blattaria, isoptera, phthiraptera, thysanoptera, heteroptera, homoptera, lepidoptera, coleoptera, hymenoptera, diptera, siphonaptera, and plant parasitic nematodes in agriculture or other fields.
The synthetic order (Syrnphyla) is, for example, white pine moth (Scutigerella immaculate) or the like.
The order Orthoptera (Orthoptera), for example, cricket-tree (Acheta domesticus), mole cricket genus (Gryllotalpa spp.), African migratory locust (Locusta migratoria), black locust (Melanoplus spp.), desert locust (Schistocer cagregaria), and the like;
the Blattaria (Blattaria), for example, Oriental Blatta (Blatta orientalis), American Blatta (Periplanet aainecana), Florida Blatta (Leucophae amaderae), German Blatta (Blattella gernanica), and the like.
The Isoptera (Isoptera), for example, Reticulitermes spp.
From the order of the Anoplura (Phthiraptera), for example, Pediculus humanus (Pediculus humanus corpporus), Hematophthirus (Haematopinus spp.), Phthirius spp (Linoganathus spp.), Phthirius spp (Trichodectenes spp.), Phthirius spp., and the like are mentioned.
From the order of the Thysanoptera (Thysanoptera), for example, Thrips palmi (Hercinothrips pernoralis), Thrips tabaci (Thrips tabaci), Thrips palmi (Thrips palmi), Thrips occidentalis (Frankliniella occidentalis), etc.
The Heteroptera (Heteroptera), for example, Douglas bugs (Eurygaster spp.), Meristus intermedia (Dysdercus internus), Piriscus quadratus (Piesna quadrata), Cimicifuga fascicularis (Cimexicanus), Primatus rudis (Rhodnius prolixus), Primatus rudis (Triatoma spp.), and the like.
From the order of the Hoinoptera (Hoinoptera), for example, whitefly (Aleurodes brassicae), tobacco powder (Beinisia tabaci), whitefly (Trialeurodes vaporariorum), cotton aphid (Aphis gossypii), cabbage aphid (Brevicyne brassiccus), Cryptophycus aurantiaca (Cryptomyces rius), Aphis nigricans (Aphis fabae), Aphis citricola (Aphis pygium), Aphis citricola (Aphis punctiferum), Aphis woolla (Eriosoma lanigerum), cercospora mume (Hyalophorus arundinis), Rhizopus vitis (Phyllophora botrys), Aphis graminearum (Phyllostachys), Aphis leptosporum (Perphugineus spp.), Aphis gramineus (Phyllospora), Aphis gramineus (Phyllocerulophycus), Phytophaga canus, Phytophilus viridula (Phyllophora), Phytophus nilotica (Phytophus nilotica), Phytopsis (Phytophus niloti ludina), Phytopsis (Phytopsis), Phytopsis (Phytophaga ludinaria), Phytopsis (Phytophaga), Phytophaga peregrina), Phytophilus (Phytophaga), Phytophaga peregrina), Phytophaga (Leporella viridotus (Leporus), Phytophaga), Phytophagi (Leporus spp), Phytophaga (Leporus spp), Phytophagi), Phytophaga (Leporella viridotus spp), Phytophaga (Leporus spp), Phytophagi), Phytophaga (Leporus spp) Pediculosis species (Psylla spp.) and the like.
The Lepidoptera (Lepidoptera), for example, Henochloropsis (Pectinophora gossypiella), Trichoplusia (Bupalus piniarius), Dipper cutworm (Cheirnathia braurita), Spirocha (Lithocolletia blanca), apple armyworm (Hypomeuta padelila), Plutella xylostella (Plutella xylostella), Trichoplusia fusca ((Malaconia neosteria), yellow moth (Euproctis chrysospora), Spodoptera (Lyinanria spp.), cotton snezoea (Bucculus thyridularia), orange snezoea (Phyllanthus reticulata), Sporidia (Sporidia spp.), Sporidia (Sporidia) and Sporidia (Sporidia spp.), Sporidia (Sporidia) Sporidia (Sporidia) and Sporidia (Sporidia) Sporidia (Sporidia), Sporidia (Sporidia), Sporidia (Sporidia) and Sporidia (Sporidia) Sporidia (Sporidia) Sporidia (Sporidia) Sporidia (Sporidia) or Sporidia (Sporidia) including Sporidia) and Sporidia (Sporidia) of Sporidia (Sporidia) of Sporidia (Sporidia) of Sporidia (Sporidia) of Sporidia (Sporidia) of Sporidia (Sporidia) of Sporidia (Sporidia) of Sporidia (Sporidia) of Sporidia (Sporidia) of Sporidia (Sporidia, The species Cnaphalocrocis (Chilo spp.), Cnaphalocrocis medinalis (Pyrausta nubilalis), Diatraea medinalis (Ephemeta kuehniella), Ceramia furnacalis (Galleria mellonella), Pleiobolus (Tineola bisselella), Baboea (Tinea pellionella), Bombycina (Menllionella), Brown looper (Hofrnannophiap Seudospermella), Linnaeus (Cacoecia podana), Plectoid moth (Choristoneura furifera), Stachys vinifera (Clysia ambigua), Camellia sinensis (Hooma moniganna irna), Tortoise viridis (Tortrix viridana), Cnaphalocrocis (Cnaphalotrus spp.), and Nepholida oryzae (Ohiophaga nivea).
The Coleoptera (Coleoptera), for example, bark beetles (Anobium puncatus), bark beetles (rhizoperthos dominica), yellowhorn beetles (Bruchidius obesus), bean weevils (acathoscopes), horsebeans (Acanthoscelides obtectus), longicorn beetles (hylolus bajulus), yellowhorn beetles (agrastica annuus), potato beetles (leprosus), horsetail beetles (Phaedon cochleariae), phyllanthus (Diabrotica spp.), stemona beetles (pseudopteris chrysospora), coccinella varivestis (phylinicola), coccinella (epilinum), sabdariae, globeformis, globeformes (nigripes), globeformes (cornus), grapevis (nigripes), brassica (purpureus), grapevis (purpureus sp), grapevis (nigra), grapevis (nigripes (purpureus), picea sp Rape pollen beetle (Meligethes aeneus), spider beetle (Ptinus spp.), yellow spider beetle (Niptus bololeuus), naked spider beetle (Gibbium psiyloides), pseudogluta sp (Triboliur spp.), yellow mealworm (Tenebnio rnolitor), click beetle (Agriotes spp.), broad chest click beetle (Conoderus spp.), Western Holotrichia gilles (Melolontha inlolontha), potato gill horn (Aihimalalon solstialis), brown New Zealand gill horn golden tortoise (Costelytra zea), rice root weevil (Li soloryphulus syzobius), and the like.
From the order Hymenoptera ((Hymenoptera), for example, genus lobela ((Dipnion spp.), genus euglena (hoplocampapa spp.), genus trichomes (Lasius spp.), genus calomel (monarnonis), genus vespid (Vespa spp.), etc.;
the Diptera (Diptera), for example, the present invention relates to a composition for treating insect pests, such as, for example, autographa, aleurodermia, Drosophila melanogaster, muscsca, Drosophila lata, Fannia spp, callimastra, Drosophila rubra, Drosophila viridans, Drosophila, chrysomyzia spp, xanthomyza, bactenaria, Drosophila, pythium spp, diaposira spp, diaposia spp, Drosophila sting, stonoxy, spenopsis, ostrinia.
The Siphonaptera (Siphonaptera), for example, Xenopsylla cheopis (Xenopsylla cheopis), Ceratophyllus spp (Ceratophyllus spp.) and the like.
Such plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus similis, hedyotis herbacea (Ditylenchus dipsaci), hemithora nematoda (Tylenchus seropenetrans), Heterodera (Heterodera spp), Globodera (Globodera spp), Meloidogyne (Meloidogyne spp), Globodera (Aphelenchus spp), Longodiscus (Looidorus spp.), Trigonella spp, Globodera (Xeronium spp), and the like.
The silicoacrylonitrile compound shown in the formula I is also suitable for preventing and treating at least one plant disease of anthracnose, leaf spot, rust disease, powdery mildew, banded sclerotial blight, leaf blight, gray mold, southern blight, damping off, gibberellic disease, full rot and target spot caused by infection of rhizoctonia, sporisorium, pseudoperonospora, monascus, phaeophycus, phaeophythora and the like. Examples of the plant having the plant fungal disease include soybean, corn, wheat, melons, rice, strawberry, peanut, cotton; examples of the plant fungal diseases include soybean rust, corn rust, wheat powdery mildew, melon powdery mildew, rice sheath blight, wheat sharp eyespot, strawberry gray mold, peanut southern blight, cotton rhizoctonia rot, wheat scab, wheat take-all and cucumber target spot, wherein the melon powdery mildew includes cucumber powdery mildew and the like; the pathogenic bacteria include Phakopsora pachyrhizi (Phakopsora pachyrhizi system.), Puccinia zeae (Puccinia sorghi Schw), Erysiphe necator (Blumeria graminis), Erysiphe cucurbitaceae (Erysiphe cucurbita), Erysiphe cucurbitae (Sphaerotheca cucurbitae), dermataceae (thanatephora cuscutaris), rhizoctonia graminis (rhizoctonia solani), and rhizoctonia solani (rhizoctonia solani), Botrytis cinerea (Botrytis cinerea per), Fusarium graminearum (Fusarium graminearum Schw.), Fusarium avenae (Fusarium avenaceum), moniliforme (Fusarium moniliforme), pythomonas oryzae (phomophilus), Pythium purpurea (phoma niponicum).
Therefore, the technical scheme of the invention also comprises the application of the silicon acrylonitrile compound shown in the formula I as a bactericide in agriculture or other fields.
The silicoacrylonitriles of formula I according to the invention can be prepared in a conventional manner into acaricide and/or insecticide and/or fungicide compositions. These active compounds can be formulated in the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active substance, microcapsules in polymers, coating compositions for seeds, and formulations for use with combustion devices, such as smoking cartridges, smoking pots and smoking trays, and ULV Cold mist (Cold mist) and hot mist (Warm mist) formulations.
These formulations can be produced by known methods, for example by mixing the active compounds with extenders, that is, liquid or liquefied gas or solid diluents or carriers, and optionally surfactants, that is, emulsifiers and/or dispersants and/or foam formers. Organic solvents may also be used as adjuvants, for example when water is used as extender.
When a liquid solvent is used as the diluent or carrier, it is basically suitable, for example: aromatic hydrocarbons such as xylene, toluene or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions; alcohols, such as ethanol or ethylene glycol and their ethers and lipids; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; or less commonly polar solvents such as dimethylformamide and dimethylsulfoxide, and water.
Liquid gas diluents or carriers refer to liquids that will become gases at normal temperature and pressure, such as aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
The solid carrier may be a finely divided natural mineral such as kaolin, clay, talc, quartz, floridin, montmorillonite, or diatomaceous earth; and ground synthetic minerals such as highly dispersed silicic acid, alumina and silicates. Solid carriers for granules are crushed and classified natural zircon, such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic coarse powders, and granules of organic materials, such as sawdust, coconut shells, corn cobs and tobacco stalks, and the like.
Nonionic and anionic emulsifying trains may be used as emulsifiers and/or foam formers. Such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, such as alkylaryl polyethylene glycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and albumin hydrolysates. The dispersant comprises lignin sulfite waste liquor and methyl cellulose.
Binders such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or emulsions, for example gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
Colorants such as inorganic dyes, e.g., iron oxide, cobalt oxide, and prussian blue; organic dyes such as azo dyes or metal phthalocyanine dyes; and with trace nutrients such as salts of iron, manganese, boron, copper, cobalt, aluminum, and zinc, and the like.
The silicon acrylonitrile compounds of formula I of the present invention may be present in their commercial preparations as a mixture with other active compounds such as insecticides, bactericides, fungicides, herbicides, growth control agents, etc., or in the dosage forms prepared from these preparations. Insecticides include, for example, phosphates, carbamates, chlorinated hydrocarbons, and substances produced by microorganisms, such as avermectins, etc., and fungicides include strobilurins, amides, triazoles, etc.
In addition, the silicon acrylonitriles of the formula I according to the invention can also be present in their commercial preparations in a mixture with synergists, which are compounds which increase the action of the active compounds, in the use forms prepared from these preparations, it being possible for no synergists to be added, since the active compounds themselves are active.
These formulations generally contain from 0.001 to 99.99% by weight, preferably from 0.01 to 99.9% by weight, more preferably from 0.05 to 90% by weight, of the active compound according to the invention, based on the total weight of the pesticidal composition. The concentration of the active compound in the commercial preparations or dosage forms to be used can vary within wide limits. The concentration of the active compound in the dosage form to be used may vary from 0.0000001 to 100% (g/v), preferably between 0.0001 and 1% (g/v), and variations and modifications are possible within the scope of the invention as defined in the claims.
The main advantages of the invention include:
(a) the compound has excellent acaricidal activity;
(b) the compound also has excellent insecticidal and bactericidal activity;
(c) the compound of the invention has short synthesis steps and better total yield;
(d) compared with the existing compounds of the same type, the compound has remarkable structural innovation;
(f) the compound has excellent acaricidal, insecticidal and bactericidal activities and has small influence on the environment.
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out under conventional conditions or conditions recommended by the manufacturers. Unless otherwise indicated, percentages and parts are percentages and parts by weight.
EXAMPLE 1 preparation of Compounds i-7
Weighing NaH (500mg, 12.5mmol) in a 50ml two-mouth bottle, adding 30ml THF, and stirring and dispersing uniformly under ice bath; trimethylsilylphenylacetonitrile (1.89g,10mmol) was weighed out and added dropwise to a suspension of NaH in THF. After further stirring for 20min, ethyl 2-trifluoromethylbenzoate (2.18g,10mmol) was added dropwise and reacted at 60 ℃. After the reaction is finished, adding a small amount of water under ice bath to quench the reaction, and adding diluted hydrochloric acid to adjust the reaction to be acidic. Extraction with ethyl acetate (20 mL. times.3), combining the organic phases, washing with saturated sodium chloride solution, and drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was taken up in n-heptane to precipitate a white solid in 84.2% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 74.2%.1H NMR(400MHz,Chloroform-d)δ7.68(d,J=7.6Hz,1H),7.58(d,J=7.8Hz,1H),7.49(t,J=7.5Hz,1H),7.43(d,J=7.6Hz,1H),7.38(d,J=8.1Hz,2H),7.33(d,J=8.0Hz,2H),0.85(s,9H),0.09(s,9H).
EXAMPLE 2 preparation of Compounds i-4
Weighing NaH (500mg, 12.5mmol) in a 50ml two-mouth bottle, adding 30ml THF, and stirring and dispersing uniformly under ice bath; trimethylsilylphenylacetonitrile (1.89g,10mmol) was weighed out and added dropwise to a suspension of NaH in THF. After further stirring for 20min, ethyl 2-trifluoromethylbenzoate (2.18g,10mmol) was added dropwise and reacted at 60 ℃. After the reaction is finished, adding a small amount of water under ice bath to quench the reaction, and adding diluted hydrochloric acid to adjust the reaction to be acidic. Extraction with ethyl acetate (20 mL. times.3), combining the organic phases, washing with saturated sodium chloride solution, and drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was taken up in n-heptane to precipitate a white solid in 84.2% yield. The white solid is subsequently dissolved in 20ml of dichloromethane and triethyl chloride is addedAfter stirring amine (1.01g,10mmol) at room temperature for 10min, isobutyryl chloride (1.25g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 77.6%.1H NMR(400MHz,Chloroform-d)δ7.68(d,J=7.6Hz,1H),7.58(d,J=7.8Hz,1H),7.49(t,J=7.5Hz,1H),7.43(d,J=7.6Hz,1H),7.38(d,J=8.1Hz,2H),7.33(d,J=8.0Hz,2H),2.69–2.54(m,1H),0.95(d,J=6.7Hz,6H),0.28(s,9H).
EXAMPLE 3 preparation of Compounds i-24
Weighing NaH (500mg, 12.5mmol) in a 50ml two-mouth bottle, adding 30ml THF, and stirring and dispersing uniformly under ice bath; trimethylsilylphenylacetonitrile (1.89g,10mmol) was weighed out and added dropwise to a suspension of NaH in THF. After further stirring for 20min, ethyl 2-trifluoromethylbenzoate (2.18g,10mmol) was added dropwise and reacted at 60 ℃. After the reaction is finished, adding a small amount of water under ice bath to quench the reaction, and adding diluted hydrochloric acid to adjust the reaction to be acidic. Extraction with ethyl acetate (20 mL. times.3), combining the organic phases, washing with saturated sodium chloride solution, and drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was taken up in n-heptane to precipitate a white solid in 84.2% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, benzoyl chloride (1.75g, 12.5mmol) was added dropwise and the reaction was carried out at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 44.2%.1H NMR(400MHz,Chloroform-d)δ7.68-7.48(m,6H),7.44-7.23(m,3H),7.38(d,J=8.1Hz,2H),7.33(d,J=8.0Hz,2H),0.09(s,9H).
EXAMPLE 4 preparation of Compounds i-39
NaH (500mg, 12.5mmol) was weighed into a 50ml two-necked flask and added30ml of THF, stirring and dispersing evenly under ice bath; trimethylsilylphenylacetonitrile (1.89g,10mmol) was weighed out and added dropwise to a suspension of NaH in THF. After further stirring for 20min, ethyl 2-trifluoromethylbenzoate (2.18g,10mmol) was added dropwise and reacted at 60 ℃. After the reaction is finished, adding a small amount of water under ice bath to quench the reaction, and adding diluted hydrochloric acid to adjust the reaction to be acidic. Extraction with ethyl acetate (20 mL. times.3), combining the organic phases, washing with saturated sodium chloride solution, and drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was taken up in n-heptane to precipitate a white solid in 84.2% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added thereto, and the mixture was stirred at room temperature for 10min, and ethyl 2-methoxychloroformate (1.73g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 38.4%.1H NMR(400MHz,CDCl3)δ7.68(d,J=7.6Hz,1H),7.58(d,J=7.8Hz,1H),7.49(t,J=7.5Hz,1H),7.43(d,J=7.6Hz,1H),7.38(d,J=8.1Hz,2H),7.33(d,J=8.0Hz,2H),4.58–4.39(m,2H),3.64(t,J=4.8Hz,2H),3.32(s,3H),0.30(s,9H).
EXAMPLE 5 preparation of Compounds i-58
Weighing NaH (500mg, 12.5mmol) into a 50ml two-mouth bottle, adding 30ml THF, and stirring and dispersing uniformly under ice bath; trimethylsilylphenylacetonitrile (1.89g,10mmol) was weighed out and added dropwise to a suspension of NaH in THF. After further stirring for 20min, ethyl 2-trifluoromethylbenzoate (2.18g,10mmol) was added dropwise and reacted at 60 ℃. After the reaction is finished, adding a small amount of water under ice bath to quench the reaction, and adding diluted hydrochloric acid to adjust the reaction to be acidic. Extraction with ethyl acetate (20 mL. times.3), combining the organic phases, washing with saturated sodium chloride solution, and drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was taken up in n-heptane to precipitate a white solid in 84.2% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added thereto, the mixture was stirred at room temperature for 10min, and dimethylcarbamoyl chloride (1.34g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the pressure is reducedRemoving the solvent, washing with ethyl acetate, filtering, concentrating the filtrate, and purifying by column chromatography to obtain the target compound with a yield of 54.2%.1H NMR(400MHz,Chloroform-d)δ7.68(d,J=7.6Hz,1H),7.58(d,J=7.8Hz,1H),7.49(t,J=7.5Hz,1H),7.43(d,J=7.6Hz,1H),7.38(d,J=8.1Hz,2H),7.33(d,J=8.0Hz,2H),5.00(hept,J=6.2Hz,1H),3.22(s,6H),0.15(s,9H).
EXAMPLE 6 preparation of Compounds i-71
Weighing NaH (500mg, 12.5mmol) in a 50ml two-mouth bottle, adding 30ml THF, and stirring and dispersing uniformly under ice bath; paradimethylvinylsilylphenylacetonitrile (2.01g,10mmol) was weighed out and added dropwise to a suspension of NaH in THF. After further stirring for 20min, ethyl 2-trifluoromethylbenzoate (2.18g,10mmol) was added dropwise and reacted at 60 ℃. After the reaction is finished, adding a small amount of water under ice bath to quench the reaction, and adding diluted hydrochloric acid to adjust the reaction to be acidic. Extraction with ethyl acetate (20 mL. times.3), combining the organic phases, washing with saturated sodium chloride solution, and drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure and column chromatography gave a brown oil in 71.8% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, and the target compound is obtained after the filtrate is concentrated and purified by column chromatography, wherein the yield is 81.0%.1H NMR(400MHz,Chloroform-d)δ7.68(d,J=7.6Hz,1H),7.58(d,J=7.8Hz,1H),7.49(t,J=7.5Hz,1H),7.43(d,J=7.5Hz,1H),7.38(d,J=8.1Hz,2H),7.33(d,J=8.0Hz,2H),6.28(dd,J=20.0,14.5Hz,1H),6.09(dd,J=14.5,3.6Hz,1H),5.72(dd,J=20.2,3.8Hz,1H),0.89(s,9H),0.35(s,6H).
EXAMPLE 7 preparation of Compounds i-134
NaH (500mg, 12.5mmol) was weighed into 50ml, adding 30ml of THF into a two-mouth bottle, and stirring and dispersing uniformly under ice bath; paradimethyl tert-butylsilylphenylacetonitrile (2.31g,10mmol) was weighed out and added dropwise to a suspension of NaH in THF. After further stirring for 20min, ethyl 2-trifluoromethylbenzoate (2.18g,10mmol) was added dropwise and reacted at 60 ℃. After the reaction is finished, adding a small amount of water under ice bath to quench the reaction, and adding diluted hydrochloric acid to adjust the reaction to be acidic. Extraction with ethyl acetate (20 mL. times.3), combining the organic phases, washing with saturated sodium chloride solution, and drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was taken up in n-heptane to precipitate a white solid in 82.8% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 74.2%.1H NMR(400MHz,Chloroform-d)δ7.68(d,J=7.6Hz,1H),7.58(d,J=7.8Hz,1H),7.49(t,J=7.5Hz,1H),7.43(d,J=7.6Hz,1H),7.38(d,J=8.1Hz,2H),7.33(d,J=8.0Hz,2H),0.89(s,9H),0.86(s,9H),0.30(s,6H).
EXAMPLE 8 preparation of Compounds i-313
Weighing NaH (500mg, 12.5mmol) in a 50ml two-mouth bottle, adding 30ml THF, and stirring and dispersing uniformly under ice bath; m-trimethylsilylphenylacetonitrile (1.89g,10mmol) was weighed out and added dropwise to a suspension of NaH in THF. After further stirring for 20min, ethyl 2-trifluoromethylbenzoate (2.18g,10mmol) was added dropwise and reacted at 60 ℃. After the reaction is finished, adding a small amount of water under ice bath to quench the reaction, and adding diluted hydrochloric acid to adjust the reaction to be acidic. Extraction with ethyl acetate (20 mL. times.3), combining the organic phases, washing with saturated sodium chloride solution, and drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was taken up in n-heptane to precipitate a white solid in 87.9% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, and ethyl acetateWashing and filtering the ester, concentrating the filtrate, and purifying by column chromatography to obtain the target compound with the yield of 85.2%.1H NMR(400MHz,Chloroform-d)δ7.85(d,J=7.6Hz,1H),7.73(d,J=7.5Hz,1H),7.64(t,J=7.5Hz,1H),7.58(d,J=7.1Hz,2H),7.47(dd,J=17.7,7.5Hz,2H),7.36(t,J=7.5Hz,1H),0.95(s,9H),0.25(s,9H).
EXAMPLE 10 preparation of Compounds ii-4
A two-necked flask was charged with ethyl 1,3, 4-trimethylpyrazole-5-carboxylate (1.82g,10mmol), p-trimethylsilylacetonitrile (1.89g,10mmol), n-hexane 30ml, and ethylene glycol monomethyl ether 5ml, followed by addition of a water separator and a reflux condenser. After the nitrogen replacement of the reaction system, the reaction system was refluxed at 110 ℃ for 2 hours and then cooled to 100 ℃. After the temperature had stabilized, sodium methoxide solution (2M, 6ml, 12.0mmol) was added dropwise. After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the aqueous phase was acidified by adding dilute hydrochloric acid, extracted with ethyl acetate (20 mL. times.3), the organic phases were combined, washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a white solid in 74.8% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, isobutyryl chloride (1.25g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 84.2%.1H NMR(400MHz,Chloroform-d)δ7.60–7.50(m,4H),3.91(s,3H),2.21(s,3H),2.10(s,3H),2.69–2.54(m,1H),0.95(d,J=6.7Hz,6H),0.29(s,9H).
EXAMPLE 9 preparation of Compounds ii-7
Adding 1,3, 4-trimethylpyrazole-5-ethyl formate (1.82g,10mmol), p-trimethylsilylbenzacetonitrile (1.89g,10mmol), n-hexane 30ml, ethylene glycol monoethyl ether5ml of dimethyl ether were added, followed by a water separator and a reflux condenser. After the nitrogen replacement of the reaction system, the reaction system was refluxed at 110 ℃ for 2 hours and then cooled to 100 ℃. After the temperature had stabilized, sodium methoxide solution (2M, 6ml, 12.0mmol) was added dropwise. After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the aqueous phase was acidified by adding dilute hydrochloric acid, extracted with ethyl acetate (20 mL. times.3), the organic phases were combined, washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a white solid in 84.2% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 74.8%.1H NMR(400MHz,Chloroform-d)δ7.60–7.50(m,4H),3.91(s,3H),2.21(s,3H),2.10(s,3H),1.16(s,9H),0.29(s,9H).
EXAMPLE 11 preparation of Compounds ii-39
A two-necked flask was charged with ethyl 1,3, 4-trimethylpyrazole-5-carboxylate (1.82g,10mmol), p-trimethylsilylacetonitrile (1.89g,10mmol), n-hexane 30ml, and ethylene glycol monomethyl ether 5ml, followed by addition of a water separator and a reflux condenser. After the nitrogen replacement of the reaction system, the reaction system was refluxed at 110 ℃ for 2 hours and then cooled to 100 ℃. After the temperature had stabilized, sodium methoxide solution (2M, 6ml, 12.0mmol) was added dropwise. After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the aqueous phase was acidified by adding dilute hydrochloric acid, extracted with ethyl acetate (20mL × 3), the organic phases were combined, washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a white solid in 84.2% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added thereto, and the mixture was stirred at room temperature for 10min, and ethyl 2-methoxychloroformate (1.73g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, decompressing to remove the solvent, washing and filtering by ethyl acetate, concentrating the filtrate, purifying by column chromatography to obtain the target compound,the yield was 78.7%.1H NMR(400MHz,Chloroform-d)δ7.60–7.50(m,4H),4.58–4.39(m,2H),3.91(s,3H),3.64(t,J=4.8Hz,2H),3.32(s,3H),2.21(s,3H),2.10(s,3H),0.29(s,9H).
EXAMPLE 12 preparation of Compounds ii-24
A two-necked flask was charged with ethyl 1,3, 4-trimethylpyrazole-5-carboxylate (1.82g,10mmol), p-trimethylsilylacetonitrile (1.89g,10mmol), n-hexane 30ml, and ethylene glycol monomethyl ether 5ml, followed by addition of a water separator and a reflux condenser. After the nitrogen replacement of the reaction system, the reaction system was refluxed at 110 ℃ for 2 hours and then cooled to 100 ℃. After the temperature had stabilized, sodium methoxide solution (2M, 6ml, 12.0mmol) was added dropwise. After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the aqueous phase was acidified by adding dilute hydrochloric acid, extracted with ethyl acetate (20 mL. times.3), the organic phases were combined, washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a white solid in 84.2% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, benzoyl chloride (1.75g, 12.5mmol) was added dropwise and the reaction was carried out at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained, wherein the yield is 64.6%.1H NMR(400MHz,Chloroform-d)δ7.68-7.48(m,6H),7.44-7.23(m,3H),7.38(d,J=8.1Hz,2H),7.33(d,J=8.0Hz,2H),2.21(s,3H),2.10(s,3H),1.16(s,9H),0.29(s,9H).
EXAMPLE 13 preparation of Compounds ii-308
A two-necked flask was charged with ethyl 1,3, 4-trimethylpyrazole-5-carboxylate (1.82g,10mmol), 5-fluoro-3-trimethylsilylphenylacetonitrile (2.07g,10mmol), n-hexane 30ml, and ethylene glycol monomethyl ether 5ml, followed by addition of a water separator and a reflux condenser. After the nitrogen replacement of the reaction system, 110Reflux at C for 2 hours, then cool to 100 ℃. After the temperature had stabilized, sodium methoxide solution (2M, 6ml, 12.0mmol) was added dropwise. After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the aqueous phase was acidified by adding dilute hydrochloric acid, extracted with ethyl acetate (20 mL. times.3), the organic phases were combined, washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the crude product. The crude product was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 88.2%.1H NMR(400MHz,Chloroform-d)δ7.85(d,J=7.6Hz,1H),7.73(d,J=7.5Hz,1H),7.36(t,J=7.5Hz,1H),3.32(s,3H),2.21(s,3H),2.10(s,3H),0.95(s,9H),0.25(s,9H).
EXAMPLE 14 preparation of Compounds ii-313
A two-necked flask was charged with ethyl 1,3, 4-trimethylpyrazole-5-carboxylate (1.82g,10mmol), m-trimethylsilylacetonitrile (1.89g,10mmol), n-hexane 30ml, and ethylene glycol monomethyl ether 5ml, followed by addition of a water separator and a reflux condenser. After the nitrogen replacement of the reaction system, the reaction system was refluxed at 110 ℃ for 2 hours and then cooled to 100 ℃. After the temperature had stabilized, sodium methoxide solution (2M, 6ml, 12.0mmol) was added dropwise. After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the aqueous phase was acidified by adding dilute hydrochloric acid, extracted with ethyl acetate (20 mL. times.3), the organic phases were combined, washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the crude product. The crude product was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 75.9%.1H NMR(400MHz,Chloroform-d)δ7.60(s,1H),7.55(d,J=7.1Hz,1H),7.47(d,J=7.9Hz,1H),7.40(t,J=7.4Hz,1H),3.99(s,3H),3.26(s,3H),2.31(s,3H),1.82(s,9H),0.29(s,9H).
EXAMPLE 15 preparation of Compounds iii-7
A two-necked flask was charged with ethyl 1-ethyl-3, 4-trimethylpyrazole-5-carboxylate (1.82g,10mmol), p-trimethylsilylphenylacetonitrile (1.89g,10mmol), n-hexane 30ml, and 1, 4-dioxane 5ml, followed by addition of a water separator and a condenser reflux tube. After the nitrogen replacement of the reaction system, the reaction system was refluxed at 110 ℃ for 2 hours and then cooled to 100 ℃. After the temperature had stabilized, sodium methoxide solution (2M, 6ml, 12.0mmol) was added dropwise. After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the aqueous phase was acidified by adding dilute hydrochloric acid, extracted with ethyl acetate (20 mL. times.3), the organic phases were combined, washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the crude product. The crude product was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 69.8%.1H NMR(400MHz,Chloroform-d)δ7.57(d,J=7.8Hz,2H),7.49(d,J=7.8Hz,2H),6.36(s,1H),4.25(q,J=7.2Hz,2H),2.30(s,3H),1.54(t,J=7.2Hz,3H),1.14(s,9H),0.28(s,9H).
EXAMPLE 16 preparation of Compounds iii-313
A two-necked flask was charged with ethyl 1-ethyl-3, 4-trimethylpyrazole-5-carboxylate (1.82g,10mmol), m-trimethylsilylphenylacetonitrile (1.89g,10mmol), n-hexane 30ml, and ethylene glycol monomethyl ether 5ml, followed by addition of a water separator and a reflux condenser. After the nitrogen replacement of the reaction system, the reaction system was refluxed at 110 ℃ for 2 hours and then cooled to 100 ℃. After the temperature had stabilized, a sodium methoxide solution (2M, 6ml, 12.0 mmol). After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the aqueous phase was acidified by adding dilute hydrochloric acid, extracted with ethyl acetate (20 mL. times.3), the organic phases were combined, washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the crude product. The crude product was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 74.2%.1H NMR(400MHz,Chloroform-d)δ7.60(s,1H),7.55(d,J=7.1Hz,1H),7.47(d,J=7.9Hz,1H),7.40(t,J=7.4Hz,1H),6.36(s,1H),4.25(q,J=7.2Hz,2H),2.30(s,3H),1.54(t,J=7.2Hz,3H),1.14(s,9H),0.28(s,9H).
EXAMPLE 17 preparation of Compounds vi-313
Two-necked flask was charged with 2-iodo-benzoic acid ethyl ester (2.76g,10mmol), m-trimethylsilylacetonitrile (1.89g,10mmol), n-hexane 30ml, and ethylene glycol monomethyl ether 5ml, followed by addition of a water separator and a reflux condenser. After the nitrogen replacement of the reaction system, the reaction system was refluxed at 110 ℃ for 2 hours and then cooled to 100 ℃. After the temperature had stabilized, sodium methoxide solution (2M, 6ml, 12.0mmol) was added dropwise. After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the aqueous phase was acidified by adding dilute hydrochloric acid, extracted with ethyl acetate (20 mL. times.3), the organic phases were combined, washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a white solid in 75.8% yield. The white solid was then dissolved in 20ml of dichloromethane, triethylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and reacted at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and purified by column chromatography, and the target compound is obtained with the yield of 79.5%.1H NMR(400MHz,Chloroform-d)δ7.60(s,1H),7.55(d,J=7.1Hz,1H),7.47(d,J=7.9Hz,1H),7.40(t,J=7.4Hz,1H),6.36(s,1H),4.25(q,J=7.2Hz,2H),2.30(s,3H),1.54(t,J=7.2Hz,3H),1.14(s,9H),0.28(s,9H).
EXAMPLE 18 preparation of Compound xv-7
Two-necked flask was charged with 3-methylthiophenezole-2-carboxylic acid ethyl ester (1.70g,10mmol), p-trimethylsilylphenylacetonitrile (1.89g,10mmol), n-hexane 30ml, and ethylene glycol monomethyl ether 5ml, followed by addition of a water separator and a reflux condenser. After the nitrogen replacement of the reaction system, the reaction system was refluxed at 110 ℃ for 2 hours and then cooled to 100 ℃. After the temperature had stabilized, sodium methoxide solution (2M, 6ml, 12.0mmol) was added dropwise. After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the aqueous phase was acidified by adding dilute hydrochloric acid, extracted with ethyl acetate (20 mL. times.3), the organic phases were combined, washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the crude product. The crude product was then dissolved in 20ml of dichloromethane, diisopropylamine (1.01g,10mmol) was added and the mixture was stirred at room temperature for 10min, pivaloyl chloride (1.50g, 12.5mmol) was added dropwise and the reaction was carried out at room temperature. After the reaction is finished, the solvent is removed under reduced pressure, ethyl acetate is used for washing and filtering, the filtrate is concentrated and then is purified by column chromatography, and the target compound is obtained, wherein the yield is 86.3%.1H NMR(400MHz,Chloroform-d)δ7.60(s,1H),7.55(d,J=7.1Hz,1H),7.47(d,J=7.9Hz,1H),7.40(t,J=7.4Hz,1H),6.36(s,1H),4.25(q,J=7.2Hz,2H),2.30(s,3H),1.54(t,J=7.2Hz,3H),1.14(s,9H),0.28(s,9H).
Other example compounds were also prepared from different starting materials with reference to the above preparation methods, and the example compounds of the present invention are shown in table 1; other silicon acrylonitrile compounds of the present invention, represented by formula I, can also be prepared using suitable starting materials, by reference to the methods of the examples described above:
table 1 structural characterization of compounds of some examples
Examples of biological Activity assays
Evaluation of acaricidal Activity against Tetranychus urticae (Tetranychus urticae)
After the compound to be tested is dissolved by dimethyl sulfoxide, the solution is diluted to different test concentrations by a water solution of triton, and the liquid medicine is uniformly sprayed on the front and back surfaces of the bean leaf cutting pieces. After the liquid medicine is dried, the mixed individuals of the tetranychus urticae are connected to the bean leaf cut pieces, and the base number is recorded. The number of live insects on the bean leaves was recorded after 192 hours of observation in a standard observation room (23-25 ℃ C., RH 40-60%). Commercial pesticide Cyenopyrafen (Cyenopyrafen) is used as a control, and a water solution of Triton is used as a blank control. The results of the activity assay of some compounds on tetranychus urticae are shown in table 2.
Table 2 partial compound tetranychus urticae activity determination results
From the above experimental results it can be seen that: the compounds of the present invention have acaricidal activity substantially equivalent to that of the control, even at lower concentrations (e.g., 50ppm) most of the compounds have 100% acaricidal activity, e.g., compounds i-4, i-5, i-6, i-7, i-19, i-24, i-27, i-36, i-37, i-39, i-43, i-55, i-58, i-67, i-70, i-88, i-91, etc.
Evaluation of insecticidal Activity against Plutella xylostella (Plutella xylostella)
Taking a culture dish, covering a layer of filter paper at the bottom of the culture dish, and dropwise adding a proper amount of tap water for moisturizing. After removing the surface wax layer from the cabbage leaves, a cabbage leaf dish having a diameter of about 6cm was prepared, and the leaf was placed in a petri dish with the back side upward. After a compound to be tested is dissolved by dimethyl sulfoxide (DMSO), the solution is diluted to different test concentrations by a water solution of Qula, and liquid medicine is uniformly sprayed on the front and back surfaces of the leaves. After the leaves are naturally dried in the shade, 1-instar larvae of the plutella xylostella are inoculated, 3 times of repetition are carried out, a commercialized pesticide Cyenopyrafen (Cyenopyrafen) is used as a control, and a water solution of Triton is used as a blank control. The dishes were transferred to a standard observation chamber (23-25 ℃, RH 40-60%). And (4) carrying out test investigation 72 hours after treatment, recording the number of dead insects and live insects of the test insects, and calculating the death rate. The results of the activity assay of some compounds on diamond back moth are shown in Table 3.
TABLE 3 determination of Plutella xylostella Activity of some Compounds
From the above experimental results it can be seen that: compared with a control compound, the compound has excellent insecticidal activity. For example, compounds i-258, i-260, i-272, i-283, i-289, i-290, i-292, i-298, i-308, i-314, ii-260, ii-265, ii-272, ii-283, ii-292, ii-298, ii-310, ii-311, ii-313, iii-272, iii-283, iii-292, iii-298, iii-310, iii-311, iii-313, ix-260, ix-313, v-313, vi-313, vii-260, viii-260, ix-260, x-313, x-260, xi-260, xii-313, xiii-260, xv-260, xvi-260 show better or superior plutella xylostella activity at 200ppm, the contrast medicine cyenopyrafen does not show related insecticidal activity, and the compound has broad insecticidal spectrum.
Evaluation of fungicidal Activity against Puccinia fabarum (Uromyces viciae-fabae)
The test compound was prepared into a test solution at a concentration of 100ppm using N, N-Dimethylformamide (DMF) containing 0.1% Tween 80. The method comprises the steps of adopting a greenhouse living potted plant method for determination, placing test crops on a sprayer for carrying out foliage spray treatment, placing the crops after being treated by a medicament in a shade place, inoculating pathogenic bacteria spores after 24 hours, and setting 3 times of repetition, wherein a commercialized pesticide Cyenopyrafen (Cyenopyrafen) is used as a control and a blank control is additionally arranged. The inoculated crops are cultured in an artificial climate chamber, the control effect is investigated after the crops are cultured for 7d and 10d respectively, and the determination result of the activity of part of compounds on the broad bean single cell rust fungus is shown in table 4.
Evaluation of fungicidal Activity against Phytophthora capsici (Phytophthora capsicii)
The test compound was prepared into a test solution at a concentration of 100ppm using N, N-Dimethylformamide (DMF) containing 0.1% Tween 80. The method comprises the steps of adopting a greenhouse living potted plant method for determination, placing a test crop on a sprayer for carrying out foliage spray treatment, placing the crop after being treated by a medicament in a shade place, inoculating pathogenic bacteria spores after 24 hours, setting 3 times of repetition, setting a commercialized pesticide Cyenopyrafen (Cyenopyrafen) as a control, and setting a blank control. The inoculated crops are cultured in a climatic chamber, the control effect is investigated after the crops are cultured for 7d and 10d respectively, and the activity determination result of part of compounds on the phytophthora capsici is shown in table 4.
Evaluation of fungicidal Activity against Pythium (Pythium)
The test compound was prepared into a test solution at a concentration of 100ppm using N, N-Dimethylformamide (DMF) containing 0.1% Tween 80. The method comprises the steps of adopting a greenhouse living potted plant method for determination, placing test crops on a sprayer for carrying out foliage spray treatment, placing the crops after being treated by a medicament in a shade place, inoculating pathogenic bacteria spores after 24 hours, and setting 3 times of repetition, wherein a commercialized pesticide Cyenopyrafen (Cyenopyrafen) is used as a control and a blank control is additionally arranged. The inoculated crops are cultured in a climatic chamber, the control effect is investigated after the crops are cultured for 7d and 10d respectively, and the determination result of the activity of part of compounds on the pythium is shown in table 4.
TABLE 4 determination of fungicidal Activity at 100ppm of some Compounds
From the above experimental results it can be seen that: compared with a control compound, the compound has excellent bactericidal activity. For example, the compounds i-4, i-5, i-6, i-7, i-19, i-24, i-27, i-36, i-37, i-39, i-43, i-51, i-55, i-58, i-67, i-70, i-71, i-83, i-88, i-91, i-102 and the like have good control effects on rust pseudomonas fabae, phytophthora capsici and pythium aphanidermatum, and the overall control effect is better than that of the control cyenopyrafen.
All documents mentioned in this application are incorporated by reference in this application as if each were individually incorporated by reference. Furthermore, it should be understood that various changes or modifications of the present invention can be made by those skilled in the art after reading the above teachings of the present invention, and these equivalents also fall within the scope of the appended claims of the present application.
Claims (11)
1. A compound of formula I, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof,
in the formula (I), the compound is shown in the specification,
R1selected from the group consisting of substituted or unsubstituted: c1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C3-6Cycloalkoxy, C1-6Alkylthio radical, C3-6Cycloalkylthio radical, C6-C10Aryl, 5-10 membered heteroaryl, 4-10 membered heterocyclyl; wherein said substitution is by one or more RaSubstitution;
R2、R3and R4Each independently selected from the group consisting of substituted or unsubstituted: hydrogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6An alkynyl group; wherein said substitution is by one or more RaSubstitution;
or, R2And R3、R3And R4Or R2And R4Together form a group selected from: - (CH)2)p-、-(CH2)o-O-(CH2)p-O-(CH2)o-; wherein o is independently 0, 1, 2, 3, or 4, and p is 2, 3,4, 5, or 6;
R5selected from the group consisting of substituted or unsubstituted: c1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C3-6Cycloalkylthio radical, R6And R7(ii) a Wherein said substitution is by one or more RaSubstitution;
R6is substituted or unsubstituted C6-14An aryl group; r6Wherein said substitution means that the hydrogen on the group is substituted with 1 to 5 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C3-6Cycloalkylthio, -CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;
R7Is unsubstituted or substituted 5-14 membered heteroaryl; r7Wherein said substitution means that the hydrogen on the group is substituted with 1 to 5 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C3-6Cycloalkylthio, -CN, NO2、SO2R8、COR8、COOR8、CONR8R9And SO2NR8R9;
R8And R9Each independently selected from the group consisting of substituted or unsubstituted: hydrogen, C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl, C6-14Aryl, 5-14 membered heteroaryl; or, R8And R9Taken together with the N atom to which they are attached form a substituted or unsubstituted 3-6 membered heterocyclyl; wherein said substitution is by one or more RaSubstitution;
each X is independently selected from the group consisting of: hydrogen, halogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6Alkyl, halo C1-6Alkoxy, -CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;
Z is selected from: CRbRcOxygen, sulfur or NRd;
(CH2)nH in (3) can be replaced by RaSubstitution;
or Z- (CH)2)n-R1The moiety is selected from the group consisting of substituted or unsubstituted: c1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl, C6-14Aryl, 5-14 membered heteroaryl; wherein said substitution is by one or more RaSubstitution;
Rb、Rceach independently selected from the group consisting of: hydrogen, halogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6Alkyl, halo C1-6Alkoxy, -CN, -NO2、-SO2R8、-COR8、-COOR8、-CONR8R9and-SO2NR8R9;
RdSelected from the group consisting of: hydrogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6An alkyl group;
Raselected from the group consisting of: hydrogen, halogen, C1-6Alkyl radical, C1-6Alkoxy, halo C1-6Alkyl, halo C1-6Alkoxy, -CN, -NO2Oxo, C3-6Cycloalkyl, 3-6 membered heterocyclyl, -SO2R10、-COR10、-COOR10、-CONR10R11and-SO2NR10R11(ii) a Wherein R is10、R11Each independently selected from the group consisting of: hydrogen, C1-6Alkyl, halo C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl, C6-14Aryl, 5-14 membered heteroaryl;
m is 0, 1, 2, 3 or 4; n is 0, 1, 2, 3 or 4.
3. The compound of formula I, its geometric isomers, stereoisomers, or an agriculturally acceptable salt or prodrug thereof, according to claim 1, wherein R is5Selected from the group consisting of substituted or unsubstituted: phenyl, naphthyl, thiazolyl, thiadiazolyl, isothiazolyl, tetrazolyl, pyridyl, thiomorpholine-S-oxide, thiomorpholine-S, S-oxide, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, oxazolyl, oxadiazolyl, isoxazolyl, furanyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl; wherein said substitution means that the hydrogen on the group is substituted by 1 to 5 groups selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C1-6Alkylthio of, C3-6Cycloalkylthio, CN, NO2、SO2R8、COR8、COOR8、CONR8R9And SO2NR8R9;R8And R9Each independently selected from the group consisting of: hydrogen, C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl.
4. A compound of formula I, as claimed in claim 1, wherein R is a geometric isomer, a stereoisomer, or an agriculturally acceptable salt or prodrug thereof5Selected from the group consisting of:
in the formula (I), the compound is shown in the specification,
g is independently 0, 1, 2, 3,4 or 5;
each R' is independently selected from the group consisting of: halogen, C1-6Alkyl radical, C2-6Alkenyl radical, C2-6Alkynyl, C3-7Cycloalkyl radical, C1-6Alkoxy radical, C1-6Alkylthio radical, C3-6Cycloalkoxy, C1-6Alkylthio of, C3-6Cycloalkylthio, CN, NO2、SO2R8、COR8、COOR8、CONR8R9And SO2NR8R9;R8And R9Each independently selected from the group consisting of: hydrogen, C1-6Alkyl radical, C3-6Cycloalkyl, 3-6 membered heterocyclyl; .
5. The compound of formula I, its geometric isomers, stereoisomers, or an agriculturally acceptable salt or prodrug thereof, according to claim 1, wherein R is2、R3And R4Each independently selected from the group consisting of: c1-6Alkyl radical, C2-4Alkenyl and C2-4Alkynyl.
6. The compound of formula I, its geometric isomers, stereoisomers, or agriculturally acceptable salts or prodrugs thereof according to claim 1, characterized in that it has the structure shown in formula I-xvi
In the formula (I), the compound is shown in the specification,
R1、R2、R3、R4x, m, n, Z are as defined in claim 1.
8. A process for preparing a compound of claim 1, a geometric isomer, a stereoisomer, or an agriculturally pharmaceutically acceptable salt or prodrug thereof, comprising the steps of:
wherein, m, n, R1、R2、R3、R4、R5X and Z are as defined in claim 1;
(s1) reacting compound A with compound B in an inert solvent in the presence of a base to give the compound of formula I.
9. Use of a compound according to any one of claims 1 to 7, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof,
(i) can be used for killing and/or controlling at least one pest of Acarina, Symphyta, Orthoptera, Blattaria, Isoptera, Anoploptera, Thysanoptera, Isoptera, Homoptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Siphonaptera and plant parasitic nematodes and/or nymphs and/or eggs thereof;
(ii) can be used for preventing and treating at least one plant disease of anthracnose, leaf spot, rust disease, powdery mildew, banded sclerotial blight, leaf blight, gray mold, southern blight, damping off, gibberellic disease, full rot and target spot caused by infection of rhizoctonia, sclerotinia, pseudoperonospora, monascus, phaeophyceae, pythium and the like;
(iii) for the preparation of a composition or formulation for killing and/or controlling mites and/or their eggs;
(iv) for insecticidal and/or bactericidal use; and/or
(v) For the production of compositions or preparations for acaricidal and/or insecticidal and/or fungicidal use.
10. A composition comprising (i) as an active ingredient a compound according to any one of claims 1 to 7, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof; and (ii) a carrier and/or surfactant.
11. A method of killing mites, insects and/or bacteria comprising the steps of: contacting mites, insects and/or bacteria with an effective amount of a compound of any one of claims 1-7, a geometric isomer, a stereoisomer thereof, or an agriculturally pharmaceutically acceptable salt or prodrug thereof or a composition of claim 10.
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CN113354677A (en) * | 2021-01-20 | 2021-09-07 | 华中师范大学 | Acrylonitrile compound and preparation method and application thereof |
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WO1996036633A1 (en) * | 1995-05-17 | 1996-11-21 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
CN110551148A (en) * | 2019-05-17 | 2019-12-10 | 华东理工大学 | compound containing silicon acyl acetonitrile, preparation method and application thereof |
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BR9608756A (en) * | 1995-05-17 | 1999-07-06 | Du Pont | Compound fungicidal composition and method for controlling plant diseases |
CN113372374B (en) * | 2021-01-20 | 2023-03-28 | 华中师范大学 | Acrylonitrile compound, preparation method and application thereof, insecticide and acaricide |
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WO1996036633A1 (en) * | 1995-05-17 | 1996-11-21 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
US6096895A (en) * | 1995-05-17 | 2000-08-01 | E. I. Du Pont De Nemours And Company | Heterocyclic dihydrazole compounds and their use for controlling fungal plant diseases |
CN110551148A (en) * | 2019-05-17 | 2019-12-10 | 华东理工大学 | compound containing silicon acyl acetonitrile, preparation method and application thereof |
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CN113354677A (en) * | 2021-01-20 | 2021-09-07 | 华中师范大学 | Acrylonitrile compound and preparation method and application thereof |
CN113354677B (en) * | 2021-01-20 | 2023-08-01 | 华中师范大学 | Acrylonitrile compound and preparation method and application thereof |
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