CN115477615A - N- (3- (benzimidazole-2-yl) phenyl) amide compound and preparation method and application thereof - Google Patents
N- (3- (benzimidazole-2-yl) phenyl) amide compound and preparation method and application thereof Download PDFInfo
- Publication number
- CN115477615A CN115477615A CN202211264973.7A CN202211264973A CN115477615A CN 115477615 A CN115477615 A CN 115477615A CN 202211264973 A CN202211264973 A CN 202211264973A CN 115477615 A CN115477615 A CN 115477615A
- Authority
- CN
- China
- Prior art keywords
- substituted
- formula
- reaction
- phenyl
- compound shown
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 N- (3- (benzimidazole-2-yl) phenyl) amide compound Chemical class 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 13
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000001263 acyl chlorides Chemical class 0.000 claims abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical class OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 238000001704 evaporation Methods 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000001514 detection method Methods 0.000 claims description 10
- 230000008020 evaporation Effects 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000004440 column chromatography Methods 0.000 claims description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000012295 chemical reaction liquid Substances 0.000 claims description 8
- JHTBOVFZNCAYFZ-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)aniline Chemical class NC1=CC=CC(C=2NC3=CC=CC=C3N=2)=C1 JHTBOVFZNCAYFZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000005457 ice water Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- TWJVNKMWXNTSAP-UHFFFAOYSA-N azanium;hydroxide;hydrochloride Chemical class [NH4+].O.[Cl-] TWJVNKMWXNTSAP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 125000003375 sulfoxide group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 5
- 238000009835 boiling Methods 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 abstract description 11
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 8
- 235000009566 rice Nutrition 0.000 abstract description 8
- 241001477931 Mythimna unipuncta Species 0.000 abstract description 6
- 241001124076 Aphididae Species 0.000 abstract description 4
- 241001498622 Cixius wagneri Species 0.000 abstract description 4
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 abstract description 4
- 238000012360 testing method Methods 0.000 abstract description 3
- AGYSXPVGOQBEKA-UHFFFAOYSA-N 1h-benzimidazole;1,1'-biphenyl Chemical group C1=CC=C2NC=NC2=C1.C1=CC=CC=C1C1=CC=CC=C1 AGYSXPVGOQBEKA-UHFFFAOYSA-N 0.000 abstract 2
- OUAAURDVPDKVAK-UHFFFAOYSA-N n-phenyl-1h-benzimidazol-2-amine Chemical class N=1C2=CC=CC=C2NC=1NC1=CC=CC=C1 OUAAURDVPDKVAK-UHFFFAOYSA-N 0.000 abstract 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 abstract 1
- 240000004658 Medicago sativa Species 0.000 abstract 1
- 240000007594 Oryza sativa Species 0.000 abstract 1
- 238000012512 characterization method Methods 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 150000004987 o-phenylenediamines Chemical class 0.000 abstract 1
- 241000238631 Hexapoda Species 0.000 description 8
- 241000209094 Oryza Species 0.000 description 7
- 239000000575 pesticide Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- 231100000225 lethality Toxicity 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000219823 Medicago Species 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 244000267960 Medicago sativa subsp glomerata Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000010413 mother solution Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- CZXZAJRUTVYGFM-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class ClC1=C(C=CC=C1)[N+](=O)[O-].ClC1=C(C=CC=C1)[N+](=O)[O-] CZXZAJRUTVYGFM-UHFFFAOYSA-N 0.000 description 1
- 241001600407 Aphis <genus> Species 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- DLOYPCWZSNUJSS-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C(=O)O)C=CC1.[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1 Chemical class [N+](=O)([O-])C=1C=C(C(=O)O)C=CC1.[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1 DLOYPCWZSNUJSS-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Insects & Arthropods (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses an N- (3- (benzimidazole-2-yl) phenyl) amide compound and a preparation method and application thereof, substituted o-nitrochlorobenzene reacts with substituted amine to generate substituted o-nitroaniline which is reduced to substituted o-phenylenediamine by iron powder, then the o-phenylenediamine is condensed with substituted m-nitrobenzoic acid to generate substituted benzimidazole biphenyl, and the substituted benzimidazole biphenyl is reduced by the iron powderSubstituted benzimidazolyl aniline is used as the original material, and then the benzimidazolyl aniline reacts with acyl chloride to prepare the N- (3- (benzimidazole-2-yl) phenyl) amide compound. The preparation method is simple and convenient to operate, and the 61 prepared new compounds are prepared by 1 H NMR and MS characterization are carried out, and insecticidal activity tests are carried out at the concentration of 200 mu g/mL, and the results show that most of the compounds have certain insecticidal activity, wherein the mortality rate of part of the compounds to armyworm is more than 85%, the mortality rate of part of the compounds to alfalfa aphid is more than 85%, and the mortality rate of part of the compounds to rice planthopper is more than 85%.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis and drug application, and particularly relates to an N- (3- (benzimidazole-2-yl) phenyl) amide compound, and a preparation method and application thereof.
Background
With the knowledge of pesticides, the continuous maturity of application and development technologies and the development of the scientific treatment theory of pests, the environment-friendly pesticide can gradually replace the high-toxicity and high-residue pesticide.
Benzimidazole as a class of benzo-heterocyclic compounds has a special structure of two N atoms, so that hydrogen bonds are easily formed between benzimidazole and enzymes and action sites in organisms. Benzimidazole and its derivatives exhibit a wide range of biological activities, such as antiviral, anticoagulant, bacteriostatic, insecticidal, etc. Some polyfluoroalkyl groups are gradually introduced into the structure of a pesticide lead compound, and a plurality of high-bioactivity pesticides containing polyfluoroalkyl structures are developed.
Disclosure of Invention
The invention aims to provide an N- (3- (benzimidazole-2-yl) phenyl) amide compound and a preparation method and application thereof, the invention takes a pyridine-imidazole bipyridyl structure as a lead, arranges electrons of the pyridine-imidazole bipyridyl structure into an alkyl benzimidazole biphenyl structure, introduces an amide group at the meta position of a middle benzene ring, and then carries out appropriate structural modification and reformation to design and synthesize a series of N- (3- (benzimidazole-2-yl) phenyl) amide compounds.
The invention provides an N- (3- (benzimidazole-2-yl) phenyl) amide compound, which has a structural formula shown in a formula (I):
in the formula (I), the substituent X is polyfluoroalkyl, alkyl, halogen, nitro or nitrile group, and the substituent R 1 Substituted or unsubstituted, when substituted, R 1 Is alkyl, phenyl or substituted alkyl, substituent R 2 Substituted or notSubstituted, when R is substituted 2 Is halogen, nitryl, nitrile group, alkoxy, alkylthio group, sulfoxide group or sulfone group, and a substituent R 3 Is alkyl, alkoxy, substituted alkyl, substituted alkoxy, phenyl, substituted phenyl, heteroaryl or substituted heteroaryl, and the substituent on the substituted phenyl and the substituted heteroaryl is alkyl, alkoxy, halogen, nitro or nitrile group.
Preferably, in formula (I), the substituent X is trifluoromethyl or heptafluoroisopropyl, and the substituent R is 1 Substituted or unsubstituted, when substituted, R 1 Is methyl, ethyl or cyclopropyl, substituent R 2 Substituted or unsubstituted, when substituted, R 2 Is 2-chloro or 4-chloro, substituent R 3 Is methyl, cyclohexyl, ethoxy, n-propoxy, n-butoxy, 2-chloroethyl, (2, 3-difluorophenyl) methyl, benzyloxy, phenyl, 2-methylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2, 6-difluorophenyl, 2, 4-dichlorophenyl, 2-trifluoromethylphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-cyanophenyl, 2-chloro-3-nitrophenyl, furan-2-yl, pyridin-3-yl, phenoxy, 2-chloropyridin-3-yl, 6-chloropyridin-3-yl or 3-ethyl-1, 4-dimethyl-1H-pyrazol-5-yl.
Further, the invention also provides a preparation method of the N- (3- (benzimidazole-2-yl) phenyl) amide compound, which comprises the following steps;
1) Using dimethyl formamide as solvent to substitute o-nitrochlorobenzene and substituted amine R 1 NH 2 Reacting at room temperature for 3-6h, stopping reaction after TLC detection reaction is completed, extracting with ethyl acetate, drying, and evaporating under reduced pressure to remove low-boiling-point substances to obtain a compound shown in formula (II);
2) Adding ethanol aqueous solution and iron powder into the compound shown in the formula (II) obtained in the step 1), dropwise adding saturated ammonium chloride aqueous solution, carrying out reflux reaction for 2-4h, stopping the reaction after TLC detection reaction is completed, filtering, extracting with ethyl acetate, drying, and removing low-boiling-point substances through reduced pressure evaporation to obtain the compound shown in the formula (III);
3) Adding substituted m-nitrobenzoic acid and phosphorus oxychloride into the compound shown in the formula (III) obtained in the step 2), heating and refluxing for 5-10 h, detecting that the reaction is complete, slowly pouring the reaction liquid into ice water after the reaction liquid is cooled to room temperature, extracting the mixture with ethyl acetate, drying, evaporating under reduced pressure to remove low-boiling-point substances, and performing column chromatography separation and purification to obtain a compound shown in the formula (IV);
4) Adding an ethanol water solution and iron powder into the compound shown in the formula (IV) obtained in the step 3), dropwise adding a saturated ammonium chloride water solution, carrying out reflux reaction for 4-8h, stopping the reaction after TLC detection reaction is completed, filtering, extracting with ethyl acetate, drying, carrying out reduced pressure evaporation to remove low-boiling-point substances, and carrying out column chromatography separation and purification to obtain a compound shown in the formula (V);
5) Dissolving the compound shown in the formula (V) obtained in the step 4) in dry tetrahydrofuran, adding triethylamine, and dropwise adding acyl chloride R under the ice salt bath condition 3 COCl, stopping reaction after TLC detection reaction is completed, filtering, evaporating under reduced pressure to remove low-boiling-point substances, and separating and purifying by column chromatography to obtain the compound shown in the formula (I).
The reaction process is as follows:
further, in the step 1), the substituted o-nitrochlorobenzene and the substituted amine R 1 NH 2 The mass ratio of (A) to (B) is 1; in the step 2), the mass ratio of the compound shown in the formula (II) to the iron powder is 1; in the step 3), the mass ratio of the compound shown in the formula (III) to the substituted m-nitrobenzoic acid to the phosphorus oxychloride is 1-1.5; in the step 4), the mass ratio of the compound shown in the formula (IV) to the iron powder is 1; in the step 5), the compound shown as the formula (V) and acyl chloride R 3 The mass ratio of COCl to triethylamine is 1.
Further, the volume amount of dimethylformamide dissolving the substituted o-nitrochlorobenzene in the step 1) is 0.5 to 3mL/mmol in terms of the amount of the substance substituting the o-nitrochlorobenzene, the volume amount of the aqueous ethanol solution dissolving the compound represented by the formula (ii) in the step 2) is 2 to 10mL/mmol in terms of the amount of the substance dissolving the compound represented by the formula (ii), the volume ratio of ethanol to water in the aqueous ethanol solution is 2 to 8, and the volume amount of tetrahydrofuran dissolving the compound represented by the formula (v) is 2 to 6mL/mmol in terms of the amount of the substance dissolving the compound represented by the formula (v).
Further, the volume of the saturated aqueous ammonium chloride solution added dropwise in the step 4) is 0.2 to 2mL/mmol in terms of the amount of the compound represented by the formula (IV).
Further, the eluents for column chromatography in step 5) are mixed with petroleum ether and ethyl acetate in a volume ratio of 3.
Further, after the reaction liquid in the step 3) is cooled to room temperature, the rate of pouring the reaction liquid into the ice water is 1-5 mL/min.
Furthermore, the invention also provides application of the N- (3- (benzimidazole-2-yl) phenyl) amide compound in preparing pesticides.
The invention has the beneficial effects that:
the preparation method is simple and convenient to operate, and the structure of the obtained product is shown in the specification 1 H NMR and MS were confirmed, and 61 target products obtained were tested for pesticidal activity, and the results indicated that: most of the compounds have certain insecticidal activity under the concentration of 200 mu g/mL, wherein the lethality of the compounds I-16, I-25, I-31, I-36, I-37, I-44, I-55 and I-61 to armyworms is more than 85%, the lethality of the compounds I-4, I-17, I-25, I-32, I-35 and I-40 to alfalfa aphids is more than 85%, and the lethality of the compounds I-7, I-8, I-10, I-20, I-27 and I-37 to rice planthoppers is more than 85%.
The compound provided by the invention is a new compound with insecticidal activity, and provides a foundation for the research and development of new pesticides.
Detailed Description
The present invention is further illustrated by the following examples, which should not be construed as limiting the scope of the invention.
EXAMPLES 1-4 preparation of Compounds II-1 to II-4
50mmoL of substituted o-nitrochlorobenzene (o-nitrochlorobenzene) was added to a 250mL three-neck flask at room temperature
The substituent X is 5-CF 3 ，5-(CF 3 ) 2 CF or 6- (CF) 3 ) 2 CF) and 50mL of DMF, stirring by magnetic force until the mixture is fully dissolved, then dropwise adding 50mmoL of amine (methylamine and cyclopropylamine), reacting for 3 hours at room temperature, detecting by TLC (thin layer chromatography) until the reaction is completely finished, then stopping the reaction, adding ethyl acetate into the reaction solution for extraction, washing an organic phase with saturated salt for three times, drying the organic phase with anhydrous magnesium sulfate, and removing low-boiling-point substances by reduced pressure evaporation to obtain compounds II-1-II-4.
Example 5-8 preparation of Compounds III-1 to III-4
To a 500mL three-necked flask equipped with a mechanical stirring and reflux condenser was added 45mmol of the compounds II-1 to II-4 and 200mL of an aqueous ethanol solution (V) Ethanol :V Water (W) = 5), heating to 80 ℃ under stirring, fully dissolving, adding 135mmol of iron powder, dropwise adding 40mL of saturated ammonium chloride aqueous solution, refluxing, stopping reaction after TLC detection reaction is complete, filtering while hot, concentrating the filtrate to 1/5 of the original volume, and adding EAnd A, extracting, washing an organic phase with saturated salt for three times, drying with anhydrous magnesium sulfate, and removing low-boiling-point substances by reduced pressure evaporation to obtain compounds III-1-III-4.
EXAMPLES 9-13 preparation of Compounds IV-1 to IV-5
30mmol of compounds III-1 to III-4 and 30mmol of substituted m-nitrobenzoic acid (m-nitrobenzoic acid) (I) are respectively added into a dry-protected 500mL round-bottom flask
H in the phenyl ring by a substituent R 2 Unsubstituted or substituted, when substituted, R 2 2-Cl or 4-Cl), adding 150mmol of phosphorus oxychloride, stirring at normal temperature to dissolve the raw materials, heating and refluxing for 6h, detecting the reaction by TCL completely, slowly pouring the reaction liquid into 500mL of ice water after the reaction liquid is cooled to room temperature, extracting the mixture by using ethyl acetate, washing an organic phase by using saturated salt solution for three times, drying by using anhydrous magnesium sulfate, removing low-boiling-point substances by reduced pressure evaporation, and separating and purifying by using column chromatography (PE: EA = 4) to obtain compounds IV-1-IV-5.
EXAMPLES 14-19 preparation of Compounds V-1 to V-5
34mmol of compounds IV-1 to IV-5 and 204mL of ethanol aqueous solution (V) are respectively added into a 1000mL three-neck flask provided with a mechanical stirring and reflux condenser tube Ethanol :V Water (W) = 5), heating to 80 ℃ under stirring, fully dissolving, adding 85mmol iron powder, dropwise adding 50mL of saturated ammonium chloride aqueous solution, continuing reflux reaction for 7h, stopping reaction after TLC detection reaction is finished, filtering while hot, concentrating the filtrate to 1/5 of the original volume, extracting with EA, washing an organic phase with saturated salt for three times, drying with anhydrous magnesium sulfate, removing low-boiling-point substances through reduced pressure evaporation, and separating by silica gel column chromatography (PE: EA = 6.
EXAMPLE 20 preparation of the target products I-1 to I-61
5mL of dry tetrahydrofuran was added to 61 50mL single-neck round-bottom flasks, 1mmol of the compounds V-1 to V-5 obtained in examples 14 to 19 and 1.2mmol of triethylamine were added to 61 50mL single-neck round-bottom flasks, respectively, followed by stirring to obtain a homogeneous mixture, and the compound was added thereto in the form of an ice salt bathV-1 to V-5 and triethylamine are slowly added with 1.5mmol of substituted acyl chloride R 3 COCl is stirred for 1-3 hours at normal temperature, TCL detects the reaction is complete, low-boiling-point substances are removed through reduced pressure evaporation to obtain a crude product, and then the crude product is separated through silica gel column chromatography (PE: EA =3: 1) to obtain target compounds I-1 to I-61, wherein specific data are shown in tables 1 and 2.
TABLE 1 physicochemical data for N- (3- (benzimidazol-2-yl) phenyl) amides
TABLE 2N- (3- (benzimidazol-2-yl) phenyl) amides 1 H NMR and MS data
EXAMPLE 21 insecticidal Activity against armyworm
Each test compound is dissolved in DMF containing 1% Tween-80 emulsifier to prepare a mother solution with the mass concentration of 2.5%, and then diluted to 200 mug/mL by using a proper amount of distilled water for later use. And (3) fully soaking a proper amount of corn leaves in the prepared liquid medicine, naturally drying in the shade, putting into a culture dish filled with filter paper, inoculating 20 heads/dish of armyworm larvae in the 3-instar middle period, culturing in an observation room at 24-27 ℃, and investigating results after 72 hours. If the body of the insect is touched by a writing brush, the dead insect is determined to be no response.
TABLE 3 Mosquicidal Activity of N- (3- (benzimidazol-2-yl) phenyl) amides
The results show that most of the compounds in Table 1 have certain insecticidal activity against armyworms at the tested concentration of 200. Mu.g/mL, and the compounds I-16, I-25, I-31, I-36, I-37, I-44, I-55 and I-61 show more than 85% of lethality against armyworms at the tested concentration of 200. Mu.g/mL.
Example 22 insecticidal Activity against Medicago Aphis
Dissolving each compound to be tested by DMF containing 1% Tween-80 emulsifier to prepare mother liquor with the mass concentration of 2.5%, and then diluting to 200 mug/mL by using a proper amount of distilled water for later use. And (3) carrying out spray treatment on the broad bean leaves with the alfalfa aphids under a Potter spray tower, culturing the treated alfalfa aphids in an observation room at the temperature of 20-22 ℃, and investigating the result after 72 hours. If the body of the insect is touched by a brush pen, no response is regarded as dead insect.
TABLE 4 aphid-killing activity of N- (3- (benzimidazol-2-yl) phenyl) amides
The results show that most of the compounds in Table 1 have certain insecticidal activity against C.lucerne at the tested concentration of 200. Mu.g/mL, and that the compounds I-4, I-17, I-25, I-32, I-35 and I-40 show a lethality of more than 85% against C.lucerne at the tested concentration of 200. Mu.g/mL.
Example 23 insecticidal Activity against Rice planthopper
Each test compound is dissolved in DMF containing 1% Tween-80 emulsifier to prepare a mother solution with the mass concentration of 2.5%, and then diluted to 200 mug/mL by using a proper amount of distilled water for later use. Fixing 4-6 rice seedlings (about 3-4 cm in length, cultivated indoors) in white quartz sand
In the culture dish, CO is connected 2 A plurality of anesthetized 3-year-old midterm nymphs of the brown planthoppers of the rice are placed under a Potter spray tower for quantitative spray treatment (the pressure is 5lb/in 2 The sedimentation amount is 4.35mg/cm 2 ) Each treatment was repeated 3 times, sprayed, covered with a clear plastic cup, placed in an observation room (24-27 ℃ C., 14h light), and the results were investigated after 72 h. When the insect is investigated, the body of the insect is touched with a brush pen lightly, and the insect is regarded as dead insect without reaction.
TABLE 5 Rice planthopper-killing activity of N- (3- (benzimidazol-2-yl) phenyl) amides
| Compound (I) | Mortality (%) | Compound (I) | Mortality (%) | Compound (I) | Mortality (%) |
| Ⅰ-1 | 40 | Ⅰ-22 | 20 | Ⅰ-43 | 35 |
| Ⅰ-2 | 30 | Ⅰ-23 | 35 | Ⅰ-44 | 0 |
| Ⅰ-3 | 25 | Ⅰ-24 | 20 | Ⅰ-45 | 25 |
| Ⅰ-4 | 65 | Ⅰ-25 | 20 | Ⅰ-46 | 25 |
| Ⅰ-5 | 30 | Ⅰ-26 | 10 | Ⅰ-47 | 45 |
| Ⅰ-6 | 45 | Ⅰ-27 | 85 | Ⅰ-48 | 40 |
| Ⅰ-7 | 95 | Ⅰ-28 | 30 | Ⅰ-49 | 35 |
| Ⅰ-8 | 95 | Ⅰ-29 | 10 | Ⅰ-50 | 35 |
| Ⅰ-9 | 40 | Ⅰ-30 | 60 | Ⅰ-51 | 30 |
| Ⅰ-10 | 95 | Ⅰ-31 | 15 | Ⅰ-52 | 0 |
| Ⅰ-11 | 45 | Ⅰ-32 | 20 | Ⅰ-53 | 40 |
| Ⅰ-12 | 35 | Ⅰ-33 | 15 | Ⅰ-54 | 65 |
| Ⅰ-13 | 30 | Ⅰ-34 | 20 | Ⅰ-55 | 15 |
| Ⅰ-14 | 0 | Ⅰ-35 | 0 | Ⅰ-56 | 0 |
| Ⅰ-15 | 40 | Ⅰ-36 | 30 | Ⅰ-57 | 20 |
| Ⅰ-16 | 15 | Ⅰ-37 | 90 | Ⅰ-58 | 0 |
| Ⅰ-17 | 25 | Ⅰ-38 | 10 | Ⅰ-59 | 25 |
| Ⅰ-18 | 0 | Ⅰ-39 | 30 | Ⅰ-60 | 0 |
| Ⅰ-19 | 45 | Ⅰ-40 | 35 | Ⅰ-61 | 15 |
| Ⅰ-20 | 85 | Ⅰ-41 | 20 | ||
| Ⅰ-21 | 20 | Ⅰ-42 | 25 |
The results show that most of the compounds in Table 1 have certain insecticidal activity against rice planthopper at the tested concentration of 200. Mu.g/mL, and the compounds I-7, I-8, I-10, I-20, I-27 and I-37 show more than 85% of lethality against rice planthopper at the tested concentration of 200. Mu.g/mL.
The description is given for the sole purpose of illustrating the invention in a practical form and the scope of the invention should not be considered limited to the exact form set forth in the examples, but rather should be understood to cover all equivalent technical solutions that may be conceived by one skilled in the art based on the inventive concept.
Claims (9)
- An N- (3- (benzimidazol-2-yl) phenyl) amide compound, which is characterized by having a structural formula shown in a formula (I):
in the formula (I), the substituent X is polyfluoroalkyl, alkyl, halogen, nitro or nitrile group, and the substituent R 1 Substituted or unsubstituted, when substituted, R 1 Is alkyl, phenyl or substituted alkyl, substituent R 2 Substituted or unsubstituted, when substituted, R 2 Is halogen, nitryl, nitrile group, alkoxy, alkylthio group, sulfoxide group or sulfone group, and a substituent R 3 Is alkyl, alkoxy, substituted alkyl, substituted alkoxy, phenyl, substituted phenyl, heteroaryl or substituted heteroaryl, and the substituent on the substituted phenyl and the substituted heteroaryl is alkyl, alkoxy, halogen, nitro or nitrile group. - 2. N- (3- (benzimidazol-2-yl) phenyl) amide compounds according to claim 1, characterized in that the substituent X is trifluoromethyl or heptafluoroisopropyl and the substituent R is 1 Substituted or unsubstituted, when substituted, R 1 Is methyl, ethyl or cyclopropyl, a substituent R 2 Substituted or unsubstituted, when substituted, R 2 Is 2-chloro or 4-chloro, substituent R 3 Is methyl, cyclohexyl, ethoxy, n-propoxy, n-butoxy, 2-chloroethyl, (2, 3-difluoro) groupPhenyl) methyl, benzyloxy, phenyl, 2-methylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2, 6-difluorophenyl, 2, 4-dichlorophenyl, 2-trifluoromethylphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-cyanophenyl, 2-chloro-3-nitrophenyl, furan-2-yl, pyridin-3-yl, phenoxy, 2-chloropyridin-3-yl, 6-chloropyridin-3-yl or 3-ethyl-1, 4-dimethyl-1H-pyrazol-5-yl.
- 3. A process for producing an N- (3- (benzimidazol-2-yl) phenyl) amide compound according to claim 1 or 2, which comprises the steps of;1) Using dimethyl formamide as solvent to substitute o-nitrochlorobenzene and substituted amine R 1 NH 2 Reacting at room temperature for 3-6h, stopping reaction after TLC detection reaction is completed, extracting with ethyl acetate, drying, and evaporating under reduced pressure to remove low-boiling-point substances to obtain a compound shown in formula (II);
2) Adding an ethanol aqueous solution and iron powder into the compound shown in the formula (II) obtained in the step 1), dropwise adding a saturated ammonium chloride aqueous solution, carrying out reflux reaction for 2-4 h, stopping the reaction after the TLC detection reaction is completed, filtering, extracting with ethyl acetate, drying, and carrying out reduced pressure evaporation to remove low-boiling-point substances to obtain a compound shown in the formula (III);
3) Adding substituted m-nitrobenzoic acid and phosphorus oxychloride into the compound shown in the formula (III) obtained in the step 2), heating and refluxing for 5-10 h, detecting that the reaction is complete, slowly pouring the reaction liquid into ice water after the reaction liquid is cooled to room temperature, extracting the mixture with ethyl acetate, drying, evaporating under reduced pressure to remove low-boiling-point substances, and performing column chromatography separation and purification to obtain a compound shown in the formula (IV);
4) Adding an ethanol water solution and iron powder into the compound shown in the formula (IV) obtained in the step 3), dropwise adding a saturated ammonium chloride water solution, carrying out reflux reaction for 4-8h, stopping the reaction after TLC detection reaction is completed, filtering, extracting with ethyl acetate, drying, carrying out reduced pressure evaporation to remove low-boiling-point substances, and carrying out column chromatography separation and purification to obtain the compound shown in the formula (V);
5) Dissolving the compound shown as the formula (V) obtained in the step 4) in dry tetrahydrofuran, adding triethylamine, and dropwise adding acyl chloride R under the condition of ice salt bath 3 COCl, stopping reaction after TLC detection reaction is completed, drying, removing low-boiling point substance by reduced pressure evaporation, and separating and purifying by column chromatography to obtain the compound shown in formula (I).
- 4. The process according to claim 3, wherein in step 1), the substituted o-nitrochlorobenzene and the substituted amine R 1 NH 2 The mass ratio of (A) to (B) is 1; in the step 2), the mass ratio of the compound shown in the formula (II) to the iron powder is 1; in the step 3), the mass ratio of the compound shown in the formula (III) to the substituted m-nitrobenzoic acid to the phosphorus oxychloride is 1-1.5; in the step 4), the mass ratio of the compound shown in the formula (IV) to the iron powder is 1; in step 5), the compound shown as the formula (V) and acyl chloride R 3 The mass ratio of COCl to triethylamine is 1-1.5.
- 5. The process according to claim 3, wherein the amount of dimethylformamide for dissolving the o-nitrochlorobenzene in the step 1) is 0.5 to 3mL/mmol in terms of the amount of the substance for dissolving the o-nitrochlorobenzene, the amount of the aqueous ethanol solution for dissolving the compound represented by the formula (II) in the step 2) is 2 to 10mL/mmol in terms of the amount of the substance for dissolving the compound represented by the formula (II), the volume ratio of ethanol to water in the aqueous ethanol solution is 2 to 8, and the amount of tetrahydrofuran for dissolving the compound represented by the formula (V) is 2 to 6mL/mmol in terms of the amount of the substance for dissolving the compound represented by the formula (V).
- 6. The method according to claim 3, wherein the volume of the saturated aqueous ammonium chloride solution added dropwise in step 4) is 0.2 to 2mL/mmol in terms of the amount of the compound represented by the formula (IV).
- 7. The preparation method according to claim 3, wherein the eluent for column chromatography in step 5) is a mixture of petroleum ether and ethyl acetate in a volume ratio of 3.
- 8. The method according to claim 3, wherein the reaction solution is poured into the ice water at a rate of 1 to 5mL/min after the reaction solution is cooled to room temperature in the step 3).
- 9. Use of the N- (3- (benzimidazol-2-yl) phenyl) amide compounds according to claim 1 or 2 for the preparation of insecticides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211264973.7A CN115477615B (en) | 2022-10-17 | 2022-10-17 | N- (3- (benzimidazol-2-yl) phenyl) amide compound and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211264973.7A CN115477615B (en) | 2022-10-17 | 2022-10-17 | N- (3- (benzimidazol-2-yl) phenyl) amide compound and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115477615A true CN115477615A (en) | 2022-12-16 |
| CN115477615B CN115477615B (en) | 2024-06-18 |
Family
ID=84396786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211264973.7A Active CN115477615B (en) | 2022-10-17 | 2022-10-17 | N- (3- (benzimidazol-2-yl) phenyl) amide compound and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115477615B (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1151424A (en) * | 1965-07-13 | 1969-05-07 | Fisons Pest Control Ltd | Benzimidazoles and compositions thereof |
| CN1638765A (en) * | 2001-07-27 | 2005-07-13 | 柯里斯公司 | Mediators of Hedgehog signaling pathways, compositions and uses related thereto |
| US20100168084A1 (en) * | 2008-05-08 | 2010-07-01 | Huber L Julie | Therapeutic compounds and related methods of use |
| US20110151018A1 (en) * | 2008-06-10 | 2011-06-23 | Brandeis University | Methods of insect control |
| US20130023571A1 (en) * | 2009-05-06 | 2013-01-24 | Syngenta Crop Protection Llc | N- ( 4-perfluoroalkyl-phenyl) -4-triazolyl-benzamides as insecticides |
| CN104780764A (en) * | 2012-09-05 | 2015-07-15 | 拜尔农作物科学股份公司 | Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or salts thereof as active substances against abiotic plant stress |
| CN110746407A (en) * | 2018-07-23 | 2020-02-04 | 南京农业大学 | Amide derivative containing benzimidazole group, preparation method and application thereof |
-
2022
- 2022-10-17 CN CN202211264973.7A patent/CN115477615B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1151424A (en) * | 1965-07-13 | 1969-05-07 | Fisons Pest Control Ltd | Benzimidazoles and compositions thereof |
| CN1638765A (en) * | 2001-07-27 | 2005-07-13 | 柯里斯公司 | Mediators of Hedgehog signaling pathways, compositions and uses related thereto |
| US20100168084A1 (en) * | 2008-05-08 | 2010-07-01 | Huber L Julie | Therapeutic compounds and related methods of use |
| US20110151018A1 (en) * | 2008-06-10 | 2011-06-23 | Brandeis University | Methods of insect control |
| US20130023571A1 (en) * | 2009-05-06 | 2013-01-24 | Syngenta Crop Protection Llc | N- ( 4-perfluoroalkyl-phenyl) -4-triazolyl-benzamides as insecticides |
| CN104780764A (en) * | 2012-09-05 | 2015-07-15 | 拜尔农作物科学股份公司 | Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or salts thereof as active substances against abiotic plant stress |
| CN110746407A (en) * | 2018-07-23 | 2020-02-04 | 南京农业大学 | Amide derivative containing benzimidazole group, preparation method and application thereof |
Non-Patent Citations (4)
| Title |
|---|
| "RN 2680675-63-0 等", STN-REGISTRY, pages 1 - 49 * |
| LEENA KEURULAINEN等: "Synthesis and biological evaluation of 2-arylbenzimidazoles targeting Leishmania donovani", BIOORG. MED. CHEM. LETT., vol. 25, pages 1933 - 1937, XP055773531, DOI: 10.1016/j.bmcl.2015.03.027 * |
| XU ZHANG等: "Synthesis and Bioactivity Evaluation of 2-Arylbenzimidazole Analogues", ASIAN JOURNAL OF CHEMISTRY, vol. 26, pages 1891 - 1894, XP055773532, DOI: 10.14233/ajchem.2014.15551 * |
| 蒋智等: "双芳环酰胺类及苯并咪唑类化合物的合成及其抗柯萨奇病毒活性研究", 中国药物化学杂志, vol. 25, pages 261 - 268 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115477615B (en) | 2024-06-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105669565B (en) | Isolonglifolane yl pyrimidines class compound and preparation method and application | |
| Chen et al. | Design, synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs | |
| CN112062759B (en) | Ethylsulfonyl-containing pyridine-1, 2, 4-oxadiazole substituted benzamide compounds and preparation method and application thereof | |
| CN106220641A (en) | Indole volution compound containing the blue hydrocarbon structure of more wound and preparation method and application | |
| CN110551070A (en) | Synthesis of camphoryl pyrimidine compounds and antitumor activity thereof | |
| CN102633741B (en) | Application of thiazole compounds in aspect of killing fresh water algae | |
| CN105524013B (en) | 4,5- bis- substitutes the preparation method of -2- substituted-amino thiazolium compounds | |
| JP3833281B2 (en) | 2,6-dichloroisonicotinic acid benzylamide derivative and plant disease control agent | |
| CN115477615B (en) | N- (3- (benzimidazol-2-yl) phenyl) amide compound and preparation method and application thereof | |
| CN105646546B (en) | The position 20 of camptothecins ester derivant and its antitumor application thereof of acid-sensitive type | |
| CN104610267B (en) | Method for efficiently synthesizing 6-alkyl pyrazolo [1,5-c ] quinazoline framework compound under non-catalytic condition | |
| CN106866699A (en) | A kind of RTIs of diaryl thienopyrimidines HIV 1 and its preparation method and application | |
| CN115583922B (en) | Fluorine-containing N- (3- (benzoxazol-2-yl) phenyl) amide compound and preparation method and application thereof | |
| CN113248518B (en) | Pyrimidine piperazine derivative and preparation method and application thereof | |
| CN113444095B (en) | Triazine substituted imidazole compound and preparation method and application thereof | |
| CN106565782B (en) | Phosphoryl pyrimidines, composition and purposes | |
| CN110054577B (en) | Compound containing urea and thiourea structure, synthetic method and application thereof | |
| CN107382969B (en) | Phenylpyrazole zwitterionic compound and application thereof in resistant pest control | |
| CN112438272A (en) | Evodiamine analog and application thereof in preventing and treating plant pathogenic fungi | |
| CN108640919B (en) | Matrine derivative and sophoridine derivative containing aryl amidine or aminoquinoline structure and preparation method thereof | |
| CN105859618B (en) | (2H, the 4H) diketone of isoquinolin 1,3 and its preparation method and purposes of the nitrile group containing cycloalkyl | |
| CN111978198A (en) | Lapterostigmatic acid derivative and preparation method and application thereof | |
| CN103724324A (en) | Imidacloprid-like ramification and preparing method thereof | |
| CN110078706A (en) | A kind of Imatinib derivative and its preparation method and application | |
| CN114409657B (en) | 4-aryl (methyl) imidazoline quinoxalinone compound and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |