CN106699732A - Preparation of pyrazole nicotinamide compound and application thereof as bactericide - Google Patents

Preparation of pyrazole nicotinamide compound and application thereof as bactericide Download PDF

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CN106699732A
CN106699732A CN201611014494.4A CN201611014494A CN106699732A CN 106699732 A CN106699732 A CN 106699732A CN 201611014494 A CN201611014494 A CN 201611014494A CN 106699732 A CN106699732 A CN 106699732A
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preparation
compound
pyrazole
nicotinamide derivative
nicotinamide
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吕献海
操海群
任自立
褚明杰
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Anhui Agricultural University AHAU
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Anhui Agricultural University AHAU
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    • 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
    • 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

Abstract

The invention discloses a pyrazole nicotinamide derivative, which has the following general formula shown as the accompanying drawing, wherein in the structural formula, R1 is shown as the accompanying drawing; R2 is H, F, Cl and CH3. In addition, the invention discloses a preparation method of the pyrazole nicotinamide derivative. The invention also discloses antimicrobial activity of the pyrazole nicotinamide derivative. The pyrazole nicotinamide derivative provided by the invention can be used as potential antimicrobial medicine.

Description

A kind of pyrazoles nicotinamide compound preparation and its as the application of bactericide
Technical field
The present invention relates to pyrazoles nicotinamide compound and preparation method thereof and purposes.
Background technology
Acid amide fungicides are the ancient bactericide of a class, and quantity occupies sizable ratio in bactericide, are had with it There is efficient bioactivity and receive significant attention.Research shows, it has Antiphytoviral, plant growth regulating, weeding, kills The important biomolecule activity such as bacterium, suppression cancer cell, inhibitory enzyme activity.
Salicylanilide is first aryl amide compound with bactericidal activity being found, on this architecture basics Various heterocycles are introduced into, and the heterocyclic compound largely with outstanding bactericidal activity is reported.The wherein sterilization containing pyridine structure Agent occupies certain ratio, such as the pyridine bacterium acid amides and fluopyram of BASF Aktiengesellschaft all have outstanding bactericidal activity And be widely used.Become additionally, due to pyrazole compound low toxicity, the substitution Quito efficiently and on its pyrazole ring, its structure There is irreplaceable effect in acid amide fungicides, such as the furametpyr of SUMITOMO CHEMICAL Co., Ltd. and Switzerland first just reach Bicyclic fluorine azoles bacterium amine etc. all there is pyrrazole structure.
Have been reported that and show that heterocycle can improve it with the action intensity of some enzymes in fungus body so as to carry in amide molecule The bactericidal activity of amide molecule high, in view of the special role of pyridine and pyrrazole structure in acid amide fungicides, present invention pyrrole Pyridine is directly connected with pyrazoles with amido link, and its bactericidal activity is measured.
The content of the invention
It is an object of the invention to provide a class novel pyrazole nicotinamide derivates and their preparation method and purposes. The present invention introduces pyridine ring and pyrazole ring with amide structure as core, synthesizes a series of new pyrazoles nicotinamide compounds.Pass through Preliminary biologicall test, the target compound of synthesis has good activity to some fungies.
Technical scheme is as follows：
1. a kind of pyrazoles nicotinamide derivates, it is characterized in that it has below formula：
R in structural formula1ForIn Any one；R2It is H, F, Cl, CH3In any one.
2. a kind of method for preparing above-mentioned nicotinamide derivative, it is made up of the following steps：
Step 1：Phenylhydrazine hydrochloride and water will be replaced to mix, it is 8 to adjust pH with inorganic base, adds ethanol, stirs and is allowed to complete Dissolving, adds Ethoxymethylenemalononitrile, is heated to reflux, TLC spikes reaction, cools down reaction solution, then is cooled with an ice bath, mistake Filter, dry crude product, ethyl alcohol recrystallization to product a.
Step 2：The solid and nicotinic acid that step 1 is synthesized are dissolved in pyridine, and POCl3 is added dropwise under ice bath, stir half an hour 50 DEG C are reacted 5 hours afterwards, and saturation Na is poured into after reacting completely2CO3In solution, filtered after being sufficiently stirred for, dry crude product, second Alcohol recrystallization to product.
Pyrazoles nicotinamide compound of the invention has obvious inhibitory action to southern corn leaf blight and Rhizoctonia cereali. Therefore pyrazoles nicotinamide compound of the invention can do potential antifungal drug.
Specific embodiment
Embodiment one：The preparation of compound 1
3.6g (0.025mol) hydrazinobenzene hydrochloride salt is dissolved in 15mL water, it is 8 to adjust pH with 10% sodium hydroxide solution, plus Enter 15mL ethanol, stirring is allowed to complete molten, adds 3.25g (0.025mol) Ethoxymethylenemalononitrile, is heated to reflux 2h.From So be cooled to ice bath cooling 2h, filtering, washing after room temperature, dry, yellow crystals a.
Take 1mmol above-claimed cpd a and 1mmol isonicotinic acid to be dissolved in 3mL pyridines, 10 be added dropwise under ice bath and drip POCl3, Stirring half an hour after stir half an hour after 50 DEG C react 5 hours, completely react after pour into 20mL saturations Na2CO3In solution, fully Filtered after stirring, dry crude product, ethyl alcohol recrystallization to compound 1.Yield 82%, mp:110-112℃.1H NMR (600MHz,cdcl3) δ 8.77 (dd, J=4.3,1.5Hz, 2H), 8.29 (s, 1H), 7.98 (s, 1H), 7.60 (d, J= 5.5Hz,2H),7.55–7.46(m,5H).MS (ESI):290.10(C16H11N5O,[M+H]+).Anal.Calcd for C16H11N5O:C,66.43；H,3.83；N,24.21；Found:C,66.32；H,3.94；N,24.35.
Embodiment two：The preparation of compound 2
Preparation method is with embodiment one.Isonicotinic acid in example one is replaced with 6- methoxies nicotinic acid.Obtain faint yellow target chemical combination Thing.Yield 74%, mp:320-323℃.1H NMR (600MHz, dmso) δ 8.75 (d, J=1.7Hz, 1H), 8.20 (dd, J= 8.5,2.3Hz, 1H), 7.97 (dd, J=8.5,0.9Hz, 2H), 7.72 (s, 1H), 7.50 (dt, J=8.6,7.7Hz, 1H), 7.40 (dd, J=15.7,7.7Hz, 2H), 7.20 (t, J=7.4Hz, 1H), 6.72 (d, J=8.5Hz, 1H), 3.85 (s, 3H) .MS(ESI):320.11(C17H13N5O2,[M+H]+).Anal.Calcd for C17H13N5O2:C,63.94；H,4.10；N, 21.93；Found:C,64.12；H,4.16；N,21.97.
Embodiment three：The preparation of compound 3
Preparation method is with embodiment one.Isonicotinic acid in example one is replaced with 6- chlorine apellagrins.Obtain faint yellow target compound. Yield 64%, mp:201-203℃.1H NMR(600MHz,cdcl3) δ 9.14 (s, 1H), 8.44 (d, J=8.1Hz, 1H), 7.98-7.90 (m, 2H), 7.73 (d, J=2.5Hz, 1H), 7.52 (d, J=3.2Hz, 1H), 7.40 (dd, J=9.5,4.8Hz, 2H), 7.27 (dt, J=17.7,4.2Hz, 2H) .MS (ESI):324.06(C16H10ClN5O,[M+H]+).Anal.Calcd for C16H10ClN5O:C,59.36；H,3.11；N,21.63；Found:C,59.42；H,3.24；N,21.71.
Example IV：The preparation of compound 4
Preparation method is with embodiment one.Isonicotinic acid in example one is replaced with 2- chlorine apellagrins.Obtain faint yellow target compound. Yield 66%, mp:164-166℃.1H NMR(600MHz,cdcl3) δ 8.66 (s, 1H), 8.53 (dd, J=4.6,1.7Hz, 1H), 8.30 (d, J=6.0Hz, 1H), 7.98 (s, 1H), 7.58-7.50 (m, 5H), 7.42 (dd, J=7.7,4.8Hz, 1H) .MS(ESI):324.06(C16H10ClN5O,[M+H]+).Anal.Calcd for C16H10ClN5O:C,59.36；H,3.11；N, 21.63；Found:C,59.40；H,3.21；N,21.69.
Embodiment five：The preparation of compound 5
Preparation method is with embodiment one.Isonicotinic acid in example one is replaced with nicotinic acid.Obtain faint yellow target compound.Yield 72%, mp:165-167℃.1H NMR (600MHz, dmso) δ 9.13 (s, 1H), 8.55 (d, J=4.6Hz, 1H), 8.28- (t, J=7.4Hz, the 1H) .MS (ESI) of 8.25 (m, 1H), 7.92-7.82 (m, 3H), 7.46-7.35 (m, 4H), 7.25:290.10 (C16H11N5O,[M+H]+).Anal.Calcd for C16H11N5O:C,66.43；H,3.83；N,24.21；Found:C,66.51； H,3.94；N,24.10.
Embodiment six：The preparation of compound 6
Preparation method is with embodiment one.4- fluorophenyl hydrazine hydrochlorides replace the hydrazinobenzene hydrochloride salt in example one.Obtain yellowish Semu Mark compound.Yield 76%, mp:215-217℃.1H NMR(600MHz,cdcl3) δ 8.78 (dd, J=4.6,1.4Hz, 2H), (m, the 2H) .MS of 8.02 (s, 1H), 7.79 (d, J=5.0Hz, 2H), 7.61 (s, 1H), 7.58-7.52 (m, 2H), 7.20-7.13 (ESI):308.09(C16H10FN5O,[M+H]+).Anal.Calcd for C16H10FN5O:C,62.54；H,3.28；N,22.79； Found:C,62.62；H,3.33；N,23.84.
Embodiment seven：The preparation of compound 7
Preparation method is with embodiment one.The isonicotinic acid in example one, 4- fluorophenyl hydrazine hydrochlorides is replaced to replace with 6- methoxies nicotinic acid Hydrazinobenzene hydrochloride salt in example one.Obtain faint yellow target compound.Yield 65%, mp:184-186℃.1H NMR(600MHz, cdcl3) δ 8.94 (d, J=2.3Hz, 1H), 8.21 (dd, J=8.9,2.2Hz, 1H), 7.94 (s, 1H), 7.52 (dd, J= 8.8,4.7Hz, 2H), 7.14 (t, J=8.5Hz, 2H), 6.82 (d, J=8.9Hz, 1H), 4.04 (s, 3H) .MS (ESI): 338.10(C17H12FN5O2,[M+H]+).Anal.Calcd for C17H12FN5O2:C,60.53；H,3.59；N,20.76； Found:C,60.64；H,3.62；N,20.72.
Embodiment eight：The preparation of compound 8
Preparation method is with embodiment one.The isonicotinic acid in example one, 4- fluorophenyl hydrazine hydrochlorides is replaced to replace example with 6- chlorine apellagrins Hydrazinobenzene hydrochloride salt in one.Obtain faint yellow target compound.Yield 66%, mp:178-180℃.1H NMR(600MHz, cdcl3) δ 9.08 (d, J=2.3Hz, 1H), 8.30 (dd, J=8.5,2.6Hz, 1H), 7.98 (s, 1H), 7.55-7.46 (m, 3H), 7.15 (dd, J=11.9,5.1Hz, 2H) .MS (ESI):342.05(C16H9ClFN5O,[M+H]+).Anal.Calcd for C16H9ClFN5O:C,56.24；H,2.65；N,20.49；Found:C,56.33；H,2.72；N,20.50.
Embodiment nine：The preparation of compound 9
Preparation method is with embodiment one.The isonicotinic acid in example one, 4- fluorophenyl hydrazine hydrochlorides is replaced to replace example with 2- chlorine apellagrins Hydrazinobenzene hydrochloride salt in one.Obtain faint yellow target compound.Yield 63%, mp:202-204℃.1H NMR(600MHz, cdcl3) δ 8.14 (s, 1H), 7.95 (d, J=8.0Hz, 1H), 7.57 (d, J=7.6Hz, 1H), 7.48 (t, J=7.9Hz, 3H),7.08(s,2H).MS(ESI):342.05(C16H9ClFN5O,[M+H]+).Anal.Calcd for C16H9ClFN5O:C, 56.24；H,2.65；N,20.49；Found:C,56.30；H,2.69；N,20.52.
Embodiment ten：The preparation of compound 10
Preparation method is with embodiment one.The isonicotinic acid in example one, 4- fluorophenyl hydrazine hydrochlorides is replaced to replace in example one with nicotinic acid Hydrazinobenzene hydrochloride salt.Obtain faint yellow target compound.Yield 70%, mp:238-240℃.1H NMR(600MHz,cdcl3)δ 8.77 (d, J=4.4Hz, 2H), 7.99 (s, 1H), 7.79 (s, 2H), 7.55 (d, J=1.3Hz, 1H), 7.43 (d, J= 7.6Hz, 2H), 7.25 (d, J=7.9Hz, 2H) .MS (ESI):308.09(C16H10FN5O,[M+H]+).Anal.Calcd for C16H10FN5O:C,62.54；H,3.28；N,22.79；Found:C,62.63；H,3.31；N,22.82.
Embodiment 11：The preparation of compound 11
Preparation method is with embodiment one.4- chlorophenylhydxazine hydrochlorides replace the hydrazinobenzene hydrochloride salt in example one, obtain yellowish Semu Mark compound.Yield 68%, mp:256-257℃.1H NMR(600MHz,cdcl3) δ 8.78 (d, J=4.7Hz, 2H), 8.02 (d, J=1.1Hz, 1H), 7.80 (d, J=4.2Hz, 2H), 7.54 (d, J=7.4Hz, 3H), 7.44 (dd, J=8.6,0.9Hz, 2H).MS(ESI):324.06(C16H10ClN5O,[M+H]+).Anal.Calcd for C16H10ClN5O:C,59.36；H,3.11； N,21.63；Found:C,59.44；H,3.23；N,21.60.
Embodiment 12：The preparation of compound 12
Preparation method is with embodiment one.The isonicotinic acid in example one, 4- chlorophenylhydxazine hydrochlorides is replaced to replace with 6- methoxies nicotinic acid Hydrazinobenzene hydrochloride salt in example one.Obtain faint yellow target compound.Yield 65%, mp:155-157℃.1H NMR(600MHz, cdcl3) δ 8.95 (d, J=1.7Hz, 1H), 8.22 (dd, J=8.9,2.0Hz, 1H), 7.95 (s, 1H), 7.50 (d, J= 8.6Hz, 2H), 7.42 (d, J=8.6Hz, 2H), 6.83 (d, J=8.9Hz, 1H), 4.05 (s, 3H) .MS (ESI):354.07 (C17H12ClN5O2,[M+H]+).Anal.Calcd for C17H12ClN5O2:C,57.72；H,3.42；N,19.80；Found:C, 57.83；H,3.50；N,19.91.
Embodiment 13：The preparation of compound 13
Preparation method is with embodiment one.The isonicotinic acid in example one, 4- chlorophenylhydxazine hydrochlorides is replaced to replace example with 6- chlorine apellagrins Hydrazinobenzene hydrochloride salt in one.Obtain faint yellow target compound.Yield 63%, mp:206-208℃.1H NMR(600MHz, cdcl3) δ 9.09 (d, J=2.2Hz, 1H), 8.32 (dd, J=8.5,2.6Hz, 1H), 7.99 (s, 1H), 7.52-7.46 (m, 3H),7.45–7.42(m,2H).MS(ESI):358.02(C16H9Cl2N5O,[M+H]+).Anal.Calcd for C16H9Cl2N5O:C,53.65；H,2.53；N,19.55；Found:C,53.72；H,2.61；N,19.66.
Embodiment 14：The preparation of compound 14
Preparation method is with embodiment one.The isonicotinic acid in example one, 4- chlorophenylhydxazine hydrochlorides is replaced to replace example with 2- chlorine apellagrins Hydrazinobenzene hydrochloride salt in one.Obtain faint yellow target compound.Yield 65%, mp:147-149℃.1H NMR(600MHz, cdcl3) δ 8.72 (s, 1H), 8.55 (d, J=4.7Hz, 1H), 8.25 (d, J=7.8Hz, 1H), 7.99 (s, 1H), 7.50- 7.47 (m, 3H), 7.43 (dd, J=7.6,4.8Hz, 1H) .MS (ESI):358.02(C16H9Cl2N5O,[M+H]+) .Anal.Calcd for C16H9Cl2N5O:C,53.65；H,2.53；N,19.55；Found:C,53.71；H,2.58；N, 19.64.
Embodiment 15：The preparation of compound 15
Preparation method is with embodiment one.The isonicotinic acid in example one, 4- chlorophenylhydxazine hydrochlorides is replaced to replace in example one with nicotinic acid Hydrazinobenzene hydrochloride salt.Obtain faint yellow target compound.Yield 72%, mp:178-180℃.1H NMR(600MHz,dmso)δ 9.13 (d, J=1.3Hz, 1H), 8.57 (dd, J=4.7,1.5Hz, 1H), 8.27 (dt, J=7.9,1.9Hz, 1H), 7.96 (d, J=8.7Hz, 3H), 7.88 (s, 1H), 7.52-7.46 (m, 2H), 7.39 (dd, J=7.7,4.8Hz, 1H) .MS (ESI): 324.06(C16H10ClN5O,[M+H]+).Anal.Calcd for C16H10ClN5O:C,59.36；H,3.11；N,21.63； Found:C,59.41；H,3.17；N,21.72.
Embodiment 16：The preparation of compound 16
Preparation method is with embodiment one.Hydrazinobenzene hydrochloride salt in example one is replaced with 4- hydrazinobenzoic acid hydrochlorides.Obtain yellowish Color target compound.Yield 73%, mp:158-160℃.1H NMR(600MHz,cdcl3) δ 9.31 (s, 1H), 8.84 (d, J= 4.5Hz, 1H), 8.37 (d, J=8.1Hz, 1H), 7.98 (s, 1H), 7.53 (dd, J=8.4,4.7Hz, 2H), 7.47 (dd, J= 8.1,4.9Hz, 1H), 7.16 (t, J=8.3Hz, 2H), 2.61 (s, 3H) .MS (ESI):304.11(C17H13N5O,[M+H]+) .Anal.Calcd for C17H13N5O:C,67.32；H,4.32；N,23.09；Found:C,67.45；H,4.39；N,23.14.
Embodiment 17：The preparation of compound 17
Preparation method is with embodiment one.Isonicotinic acid in example one is replaced with 6- methoxies nicotinic acid, with 4- hydrazinobenzoic acid hydrochlorides Instead of the hydrazinobenzene hydrochloride salt in example one.Obtain faint yellow target compound.Yield 71%, mp:180-182℃.1H NMR (600MHz,cdcl3) δ 8.56 (d, J=1.6Hz, 1H), 8.15 (d, J=28.8Hz, 1H), 8.01 (d, J=8.7Hz, 1H), 7.91 (s, 1H), 7.36 (d, J=7.8Hz, 2H), 7.28 (d, J=7.8Hz, 2H), 6.79 (d, J=8.7Hz, 1H), 3.98 (s,3H),2.39(s,3H).MS(ESI):334.12(C18H15N5O2,[M+H]+).Anal.Calcd for C18H15N5O2:C, 64.86；H,4.54；N,21.01；Found:C,64.92；H,4.63；N,21.08.
Embodiment 18：Pyrazoles nicotinamide derivatives antifungal activity is studied
Test carries out plant pathogenic fungi biology to the pyrazoles nicotinamide derivative for synthesizing using mycelial growth suppression method Resistant determination.
Aseptically, the target compound of synthesis is dissolved in DMSO, is diluted to 100mg/mL as storing solution, taken The test liquid 1mL of configuration adds the PDA culture medium of 50 DEG C or so of 9mL in the 10mL test tubes of sterilizing, and training is poured into after mixing In foster ware.Another 1mL DMSO as blank, using pyridine bacterium acid amides as positive control.
The bacterium colony circle in same growth potential is chosen, bacteria cake is obtained with card punch, bacteria cake is inverted in above-mentioned dosing culture On the culture medium of base, each is repeated 3 times.Cultivated in incubator under the conditions of 25 ± l DEG C, measured with crossing method after 3 days Bacterium colony state diameter, averages as experimental result, calculates inhibiting rate.
Inhibiting rate=[(control colony diameter-treatment colony diameter)/control colony diameter] × 100%
The listed pyrazoles nicotinamide derivative of the present invention of table 1 is to plant pathogenic fungi:Southern corn leaf blight, Rhizoctonia cereali Suppression EC50Value (μM)
aAverage value ± standard deviation (SD) in triplicate.
Pyridine bacterium acid amides：Positive control.

Claims (3)

1. a kind of pyrazoles nicotinamide derivative, it is characterized in that it has below formula：
R in structural formula1ForIn it is any one Kind；R2It is H, F, Cl, CH3In any one.
2. the method for the nicotinamide derivative described in a kind of claim 1, it is characterized in that it is made up of the following steps：
Step 1：Phenylhydrazine hydrochloride and water will be replaced to mix, it is 8 to adjust pH with inorganic base, adds ethanol, stirs and is allowed to be completely dissolved, Ethoxymethylenemalononitrile is added, is heated to reflux, TLC spikes reaction cools down reaction solution, then is cooled with an ice bath, and filters, and does Dry crude product, ethyl alcohol recrystallization to product a.
Step 2：The solid and nicotinic acid that step 1 is synthesized are dissolved in pyridine, POCl3 are added dropwise under ice bath, 50 after stirring half an hour DEG C reaction 5 hours, completely react after pour into saturation Na2CO3In solution, filtered after being sufficiently stirred for, dry crude product, ethanol weight Crystallization to product.
3. application of the nicotinamide derivative according to claim in antimycotic.
CN201611014494.4A 2016-11-18 2016-11-18 Preparation of pyrazole nicotinamide compound and application thereof as bactericide Pending CN106699732A (en)

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CN108707114A (en) * 2018-05-03 2018-10-26 上海泰禾国际贸易有限公司 A kind of acetamides and its preparation method and application
CN108707114B (en) * 2018-05-03 2021-07-23 上海泰禾国际贸易有限公司 Acetamide compound and preparation method and application thereof
CN116987064A (en) * 2023-08-04 2023-11-03 宁夏佰斯特医药化工有限公司 Preparation method and application of pyrimidine bisnicotinamide derivative
CN116987064B (en) * 2023-08-04 2024-01-26 宁夏佰斯特医药化工有限公司 Preparation method and application of pyrimidine bisnicotinamide derivative

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