CN106928196A - A kind of pyrazolecarboxamide yl-benzamide and its production and use - Google Patents
A kind of pyrazolecarboxamide yl-benzamide and its production and use Download PDFInfo
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- CN106928196A CN106928196A CN201710270641.2A CN201710270641A CN106928196A CN 106928196 A CN106928196 A CN 106928196A CN 201710270641 A CN201710270641 A CN 201710270641A CN 106928196 A CN106928196 A CN 106928196A
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- 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
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- 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
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Abstract
The present invention relates to N (2 pyridine radicals) 2 (the pyrazolecarboxamide bases of 1,3 dimethyl 1H 5) benzamide and its production and use.With o-nitrobenzoic acid as initiation material, ortho-nitrophenyl formyl chloride is obtained through chloride, intermediate adjacent nitro N (2 pyridine radicals) benzamide is obtained through with 2 aminopyridinamides, then nitro is reduced to amido with iron powder and obtains intermediate neighbour's amino N (2 pyridine radicals) benzamide, it is last again with 1, the pyrazol formyl chlorides of 3 dimethyl 1H 5 obtain target compound N (2 pyridine radicals) 2 (the pyrazolecarboxamide bases of 1,3 dimethyl 1H 5) benzamide under triethylamine effect.The beneficial effects of the present invention are：With prominent bactericidal activity, there is prominent novelty in the field.Reaction raw materials are easy to get, and reaction condition is gentle, easily implements industrialization.
Description
Technical field
The present invention relates to a kind of pyrazolecarboxamide yl-benzamide, and in particular to N- (2- pyridine radicals) -2- (1,3- diformazans
Base -1H-5- pyrazolecarboxamides base) benzamide and its production and use.
Background technology
Adjacent formoxyl benzamide compound, such as fipronil bisamide, chlorantraniliprole have its particular mechanism and kill
Worm activity, its action target is ryanodine receptor (Ryanodine receptor).The insecticide has wide to lepidoptera pest
General insecticidal activity, higher to larva activity, the inhibitory action to binge insect is stronger, acts on crop protection and more dashes forward
Go out, with existing insecticide no interactions resistance, in addition to silkworm on evil Natural Enemies of Insects without influence, be IMP (harmful organism Synthetics
Reason) very prominent selective insecticide.In addition, research it has been shown that the insecticide to mammal have security very high,
It is epoch-making new pesticides.We have found N- (the 2- pyridines for obtaining when the Structure-activity relationship of such compound is studied
Base) bactericidal activity of -2- (1, the 3- dimethyl -1H-5- pyrazolecarboxamides base) benzamide with protrusion, it is right under 100ppm
Rhizoctonia solani Kuhn (Rhizoctorzia solani) bacteriostatic activity reaches 72.8%, is the potentiality of bactericide with exploitation.
The content of the invention
The present invention obtains N- (2- pyridine radicals) -2- (1,3- diformazans when the Structure-activity relationship of such compound is studied
Base -1H-5- pyrazolecarboxamides base) benzamide, it has prominent bactericidal activity, under 100ppm, to Rhizoctonia solani Kuhn
(Rhizoctorzia solani) bacteriostatic activity reaches 72.8%, is the potentiality of bactericide with exploitation.
The present invention solves the technical scheme that is used of above-mentioned technical problem：A kind of pyrazolecarboxamide yl-benzamide, its
Structural formula is:
The preparation method of pyrazolecarboxamide yl-benzamide, with o-nitrobenzoic acid (1) as initiation material, obtains through chloride
To ortho-nitrophenyl formyl chloride (2), intermediate adjacent nitro-N- (2- pyridine radicals) benzamide is obtained through with PA amidatioon
(3) nitro then, is reduced to amido with iron powder and obtains intermediate neighbour's amino-N- (2- pyridine radicals) benzamide (4), again finally
With 1,3- dimethyl -1H-5- pyrazol formyl chlorides target compound N- (2- pyridine radicals) -2- (1,3- is obtained under triethylamine effect
Dimethyl -1H-5- pyrazolecarboxamides base) benzamide (5).
The present invention has found N- (2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazoles first during insecticide is studied
Amide groups) bactericidal activity of the benzamide with protrusion, there is prominent novelty in the field.The present invention is with ortho-nitrophenyl first
Acid is synthesized final product N- (2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazolecarboxamides base) benzene for raw material through 4 steps
Formamide, reaction raw materials are easy to get, and reaction condition is gentle, easily implements industrialization.
Reaction equation involved by preparation technology of the invention is as follows：
In more detail, following steps are included：
The preparation of intermediate adjacent nitro-N- (2- pyridine radicals) benzamide (3)：By a certain amount of o-nitrobenzoic acid and dichloro
Sulfoxide is added in flask, is heated to reflux, and decompression boils off solvent, obtains ortho-nitrophenyl formyl chloride.One is added in there-necked flask
, be slowly added dropwise ortho-nitrophenyl formyl chloride anhydrous THF solution into three mouthfuls of burnings under low temperature by quantitative solvent, acid binding agent and PA
In bottle, stirring reaction, TLC tracking reactions, question response terminates, and is diluted with ethyl acetate and water, and aqueous layer with ethyl acetate extraction is closed
And organic layer, organic layer 1.2mol/L NaHCO3The aqueous solution is washed till neutrality, is then washed with saturated common salt, anhydrous Na2SO4It is dry
It is dry, filtering, depressurize precipitation, obtains solid product, ethanol：Water=10：1 is recrystallized to give 2- nitros-N- (2- pyridine radicals) benzene first
Acid amides, yield：81%, m.p.153~155 DEG C.
The mol ratio of reaction raw materials is o-nitrobenzoic acid：Thionyl chloride=1：1~5, wherein most preferably 1：2.
Reaction dissolvent is dichloromethane, chloroform, dioxane, ether, THF etc., wherein most preferably THF.
Acid binding agent is potassium carbonate, triethylamine, pyridine etc., most preferably triethylamine.
Reaction temperature is 50 DEG C~100 DEG C, wherein most preferably 60 DEG C.
Reaction time is 3h~10h, most preferably 6h.
The preparation of intermediate neighbour's amino-N- (2- pyridine radicals) benzamide (4), solvent is added in 100mL there-necked flasks
And glacial acetic acid, it is subsequently adding adjacent nitro-N- (2- pyridine radicals) benzamide (3) and a certain amount of reduced iron powder, heating stirring, TLC
Tracking reaction, question response terminates, filters while hot, is extracted with ethyl acetate after filtrate concentration, merges organic layer, and organic layer is used
NaHCO3Solution is washed till neutrality, is then washed with saturated common salt, anhydrous Na2SO4Dry, filtering obtains 2- amino-N- (2- pyridines
Base) benzamide (4) faint yellow solid, yield：80%, m.p.135~137 DEG C.
Adjacent nitro-N- (2- pyridine radicals) benzamide：Iron powder=1：1~10, wherein most preferably 1：5；
Reaction acid used and solvent are dilute sulfuric acid, watery hydrochloric acid, acetic acid etc., wherein most preferably acetic acid.
Reaction temperature is 10 DEG C~100 DEG C, wherein most preferably 40 DEG C.
Reaction time is 3h~10h, most preferably 4h.
The system of target product N- (2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazolecarboxamides base) benzamide (5)
It is standby, solvent, acid binding agent and adjacent amino-N- (2- pyridine radicals) benzamide (4) are added in flask, will under ice bath and strong stirring
1, the 3- dimethyl pyrazole -5- formyl chlorides of a certain amount of brand-new are slowly added in flask in batches, stirring reaction 1h, TLC tracking reaction,
Question response terminates, and is poured into frozen water, is concentrated under reduced pressure, and is extracted with ethyl acetate, and merges organic layer, organic layer NaHCO3The aqueous solution
Neutrality is washed till, is then washed with saturated common salt, anhydrous Na2SO4Dry, filtering, depressurize precipitation, column chromatography obtains target product
Thing N- (2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazolecarboxamides base) benzamide (5).White solid, yield 42%,
Mp.146~150 DEG C.
The mol ratio of reaction raw materials is 2- amino-N- (2- pyridine radicals) benzamide：1,3- dimethyl pyrazole -5- formyl chlorides
=1：1~3, wherein most preferably 1：1.5.
Reaction dissolvent is dichloromethane, chloroform, dioxane, ether, THF etc., wherein most preferably THF.
Acid binding agent is potassium carbonate, triethylamine, pyridine etc., most preferably triethylamine.
Reaction temperature is -5 DEG C~10 DEG C, wherein most preferably 0 DEG C.
Reaction time is 0.5h~3h, most preferably 1h.
The beneficial effects of the present invention are：Compound N of the invention-(2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrroles
Azoles formamido) bactericidal activity of the benzamide with protrusion, there is prominent novelty in the field.In addition, with adjacent nitro
Benzoic acid is synthesized final product N- (2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazolecarboxamides for raw material through 4 steps
Base) benzamide, reaction raw materials are easy to get, and reaction condition is gentle, easily implements industrialization.
Specific embodiment
Following examples further illustrate N- (the 2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazolecarboxamides base) benzene
The Preparation method and use of formamide.
Embodiment 1
The preparation of intermediate adjacent nitro-N- (2- pyridine radicals) benzamide (3), by 4.18g (0.025mo1) ortho-nitrophenyl
Formic acid and 20mL thionyl chlorides are added in 50mL flasks, are heated to reflux 6h, and decompression boils off solvent, obtains ortho-nitrophenyl formyl
Chlorine, adds 15mL anhydrous THF, 5g (0.05mo1) triethylamines and 4.28g (0.02mo1) 2- amino pyrroles in 50mL there-necked flasks
Pyridine, 0 DEG C stirring under ortho-nitrophenyl formyl chloride anhydrous THF solution is slowly added dropwise in there-necked flask, stirring reaction 1h, TLC with
Track reacts, and question response terminates, and is diluted with 30mL ethyl acetate and 25mL water, and aqueous layer with ethyl acetate (20mL × 2) extraction merges
Organic layer, organic layer 1.2mol/L NaHCO3The aqueous solution is washed till neutrality, is then washed with saturated common salt, anhydrous Na2SO4It is dry
It is dry, filtering, depressurize precipitation, ethanol：Water=10：1 is recrystallized to give white solid, yield：81%, m.p.153~155 DEG C.
Embodiment 2
The preparation of intermediate neighbour's amino-N- (2- pyridine radicals) benzamide (4), 15mL is added in 100mL there-necked flasks
THF, 40mL H2O, 5mL glacial acetic acid, 3.6g (0.014mo1) adjacent nitros-N- (2- pyridine radicals) benzamide (3) and 3.92g
(0.07mo1) reduced iron powder, heating stirring 4h at 40 DEG C, TLC tracking reaction, question response terminates, filters while hot, after filtrate concentration
Extracted with ethyl acetate (30mL × 3), merge organic layer, organic layer 1.2mol/L NaHCO3Solution is washed till neutrality, Ran Houyong
Saturated common salt is washed, anhydrous Na2SO4Dry, filtering, obtain adjacent amino-N- (2- pyridine radicals) benzamide, faint yellow solid is produced
Rate：80%, m.p.135~137 DEG C.
Embodiment 3
The system of target product N- (2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazolecarboxamides base) benzamide (5)
It is standby, in 25mL single-necked flasks add 15mL anhydrous THF, 252mg (2.5mmol) triethylamines and 261mg (1mmol) neighbour amino-
Under N- (2- pyridine radicals) benzamide (4), ice bath and strong stirring by 1, the 3- dimethyl pyrazoles of 220mg (1.5mmol) brand-new-
5- formyl chlorides are slowly added in flask in batches, and stirring reaction 1h, TLC tracking reaction, question response terminates, is poured into 20mL frozen water,
About 10mL is concentrated under reduced pressure into, is extracted with ethyl acetate (10mL × 3), merge organic layer, organic layer 1.2mol/L NaHCO3Water
Solution is washed till neutrality, is then washed with saturated common salt, anhydrous Na2SO4Dry, filtering, depressurize precipitation, obtain faint yellow solid, post layer
Analysis obtains N- (2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazolecarboxamides base) benzamide (5) white solid, produces
Rate 42%, mp.146~150 DEG C MS, m/Z (%)：336(M+1)+1H-NMR:(CDCl3, 400MHz), δ:2.30(s,3H),
4.16 (s, 3H), 6.67 (s, 1H), 7.13~7.27 (m, 2H), 7.58~7.60 (m, 1H), 7.76~7.82 (m, 2H), 8.28
~8.37 (m, 2H), 8.75 (d, J=5.6MHz, 1H), 9.00 (s, 1H), 11.73 (s, 1H), Ana1.calcd for
C18H17N5O2C 64.47,H 5.11,N 20.88；found C 63.30,H 4.70,N 20.16.
Embodiment 4
The synthesis of 1,3- dimethyl pyrazole -5- formyl chlorides, 20ml absolute methanols are dissolved in by 0.69g (0.03mol) metallic sodium
Sodium alkoxide methanol solution is made, in the mixed of 1.16g (0.02mol) acetone and 2.92g (0.02mol) diethy-aceto oxalate is added dropwise under ice bath
Compound, stirring reaction 6h at 60 DEG C.Remove partial solvent under reduced pressure, cool down, to adding appropriate 5ml concentrated hydrochloric acids in Liquid Residue, and drip
Plus 2g hydrazine hydrates, then in stirring reaction 1 hour at 60 DEG C.Cooling, add suitable quantity of water dilution after, with ethyl acetate (20ml ×
3) extract, anhydrous Na2SO4Dry, be concentrated to give brown liquid, to appropriate 4g (0.032mol) dimethyl suflfate of its addition, rise
2h is reacted at warm to 85 DEG C, is cooled down, add 6mol/L sodium hydrate aqueous solutions to adjust pH to alkalescence, be warming up to 80 DEG C, stir 2h, it is cold
But pH to highly acid is adjusted with concentrated hydrochloric acid afterwards, is stood, suction filtration dries to obtain light yellow solid after washing, alcohol-water recrystallizes white
Platelet, under the conditions of 0 DEG C, adds 20ml thionyl chlorides, and flow back 6h, and normal pressure is evaporated off excessive thionyl chloride, obtains colourless liquid
1.63g, yield 51%.
Synthetic route is as follows：
Embodiment 5
Rhizoctonia solani Kuhn (Rhizoctorzia solani) bacteriostatic activity is carried out to target compound using Plating to survey
Examination, upper strain is followed by by the way that reagent agent is well mixed with not solidified culture medium, with pastille culture medium culture pathogen, is led to
The growth rate (diameter of bacterium colony) of pathogen is crossed to judge the bacteriostatic activity of reagent agent.Method of testing is as follows：Take 1mL
(1000ppm) medicament to be measured, by itself and the culture medium solution by volume 1 for melting：9 ratio is added to a diameter of 7cm cultures
Fully shaken up in ware, pastille culture medium be obtained after cooling, with add it is isometric without culture medium obtained in drug solns to compare.
The bacteria cake cultivated on culture medium is intercepted with the card punch of a diameter of 4mm, its microbiological contamination is faced and is sowed to culture medium central, every group
Test sets 3 repetitions, and 24~48h is cultivated at being placed in 25 ± 1 DEG C
Compound N-(2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazolecarboxamides base) benzene first prepared by embodiment 1
Acid amides has prominent bactericidal activity, under 100ppm, to Rhizoctonia solani Kuhn (Rhizoctorzia solani) bacteriostatic activity
Reach 72.8%.
N- (2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazolecarboxamides base) benzamide raw materials for production are easy to get, raw
Production. art is simple, and it has prominent bactericidal activity, under 100ppm, to Rhizoctonia solani Kuhn (Rhizoctorzia
Solani) bacteriostatic activity reaches 72.8%, is the potentiality of bactericide with exploitation.
Claims (3)
1. a kind of pyrazolecarboxamide yl-benzamide, its structural formula is：
2. the preparation method of the pyrazolecarboxamide yl-benzamide described in claim 1, with o-nitrobenzoic acid as initiation material,
Ortho-nitrophenyl formyl chloride is obtained through chloride, intermediate adjacent nitro-N- (2- pyridine radicals) is obtained through with PA amidatioon
Benzamide, is then reduced to amido and obtains intermediate neighbour's amino-N- (2- pyridine radicals) benzamide, finally with iron powder by nitro
Again with 1,3- dimethyl -1H-5- pyrazol formyl chlorides triethylamine effect under obtain target compound N- (2- pyridine radicals) -2- (1,
3- dimethyl -1H-5- pyrazolecarboxamides base) benzamide.
3. N- (2- pyridine radicals) -2- (1,3- dimethyl -1H-5- pyrazolecarboxamides base) benzamide described in claim 1 is made
It is the application of bactericide.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109081810A (en) * | 2018-09-20 | 2018-12-25 | 沈阳药科大学 | The synthetic method of 1- methyl-3-((methylamino) methyl)-1H- pyrazoles-5- nitrile |
| CN112410808A (en) * | 2020-10-04 | 2021-02-26 | 浙江埃森化学有限公司 | Synthesis method of anthranilate pesticide containing N-pyridylpyrazole |
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| CN105777713A (en) * | 2016-04-06 | 2016-07-20 | 武汉工程大学 | N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide as well as preparation thereof and use thereof |
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| CN101701016A (en) * | 2009-11-03 | 2010-05-05 | 武汉工程大学 | N-methyl-N-o-benzoyl aminobenzene formamide compounds as well as preparation and application thereof |
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| CN112410808A (en) * | 2020-10-04 | 2021-02-26 | 浙江埃森化学有限公司 | Synthesis method of anthranilate pesticide containing N-pyridylpyrazole |
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Application publication date: 20170707 |