CN110272413A - N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate and its application - Google Patents

N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate and its application Download PDF

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CN110272413A
CN110272413A CN201910587127.0A CN201910587127A CN110272413A CN 110272413 A CN110272413 A CN 110272413A CN 201910587127 A CN201910587127 A CN 201910587127A CN 110272413 A CN110272413 A CN 110272413A
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alkyl
thiazolyl
pyridyl group
pyrazole
methyl
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CN110272413B (en
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陈平
李延赛
胡艾希
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Changsha University of Science and Technology
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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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The present invention relates to acceptable salt in the pyridyl group -5- pyrazole formylamine derivate of N- thiazolyl -1- shown in formula I and its Pesticide Science and its preparing the application in insecticide:

Description

N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate and its application
Technical field
The present invention relates to the preparation method of noval chemical compound and applications, specifically N- thiazolyl -1- pyridyl group -5- pyrazoles formyl Amine derivative preparation and its preparing the application in insecticide.
Background technique
Liu Jie etc. [organic chemistry, 2010,30 (09): 1347-1353] describes the conjunction of 5- pyrazolecarboxamide compounds At and its insecticidal activity: under 100 μ g/mL concentration, the preventive effect of compound 1 and 2 pair brown paddy plant hopper is respectively 57.6% and 64.4%, Wherein the acetylcholine esterase active inhibiting rate of 2 pairs of brown paddy plant hoppers is 75.21%, is better than Buprofezin (52.17%).
Wu etc. [Pest Management Science, 2012,68 (5): 801-810] describes novel containing acylhydrazone knot The synthesis and its insecticidal activity of the pyrazole amide derivatives of structure: compound 3 is at 200mg/L to the insecticidal activity of beet armyworm 100%；Compound 4~6 is at 20mg/L to the insecticidal activity of prodenia litura 100%；6 (R=NMe of compound2) to bollworm In the activity 100% of 25mg/L.
Liu Gang etc. [Pesticide Science journal, 2011,13 (3): 327-330] describes the synthesis of pyrazoline carboxamides derivatives And its bioactivity: in 500mg/L concentration, compound 7,8 (R=SCH2C(CH3)3), 9 (R=Cyclopropyl) and 10 (R =Cyclohexyl) to the insecticidal activity 100% of diamondback moth；Insecticidal activity 100% of the compound 8 to aphis craccivora and planthopper.
Yue Min etc. [Pesticide Science journal, 2012 (4): 449-452] describes the pyrazole amide derivatives with acylhydrazone structure Synthesis and its to the insecticidal activity of diamondback moth: it there is higher insecticidal activity (to show as stomach toxicity and refuse 3 instar larvae of diamondback moth Food activity), the wherein stomach poison activity LC of compound 1150=0.6mg/L, antifeedant activity AFC50=0.6mg/L, hence it is evident that better than sun Property reference material chlopyrifos (stomach poison activity LC50=7.4mg/L, antifeedant activity AFC50=6.5mg/L).
Wang Haiyang etc. [pesticide, 2018,57 (4): 255-258] describes the synthesis of pyrazole amide derivatives and its desinsection is lived Property: compound 12 (R=H) is respectively 94% to armyworm and diamondback moth (with the feeding of 5% acetone soln processing blade) 48h death rate With 93%；Compound 13 (R=Cl) distinguishes armyworm and diamondback moth (with the feeding of 5% acetone soln processing blade) 48h death rate For 95% and 93%.Wang Haiyang etc. [pesticide, 2016 (1): 13-16] describes the pyrazole amide derivatives of the ether containing dichloropropylene Synthesis and its insecticidal activity: under 200mg/L concentration, compound 14 (X=Cl, R=CH3), 15 (X=Cl, R=CH (CH2)2)、 16 (X=Br, R=i-C4H9) it is respectively 84%, 74% and 100% to the lethality of armyworm 48h, it is above positive control chlorine worm Amide (63%).
Mao Mingzhen etc. [pesticide, 2016 (3): 166-169] describes the pyrazole amide derivatives with Phenylpyrazole structure Synthesis and its bioactivity: 17 (R=CO of compound2) and 18 (R=CONHCH Et3) when concentration is 50mg/L, it is glutinous to east Worm insecticidal activity is respectively 80% and 60%, and to diamondback moth insecticidal activity equal 100%；Mao Mingzhen etc. [pesticide, 2017 (06): 23-26] also describe hydrazine containing oxalyl or acyl guanidine radicals pyrazolecarboxamide compounds synthesis and its insecticidal activity: compound 19 It is 70% to east armyworm insecticidal activity in concentration 10mg/L, to diamondback moth insecticidal activity 100%, to diamondback moth when 5mg/L Insecticidal activity is 80%.
Opening picture, gently grade [pesticide, 2016 (3): 170-173] describes the derivative of the 1- pyridyl group -5- pyrazole amide containing thiazole ring The synthesis and its insecticidal activity of object: when 1mg/L, the insecticidal activity 100% of 20~25 pairs of diamondback moths of compound；100mg/L concentration Under, to the insecticidal activity 100% of black peach aphid；When 10mg/L, 74% is all larger than to the insecticidal activity of planthopper, is higher than reference material chlorine Worm benzamide (58%).
Geng third newly waits [modern, 2014 (3): 21-24] to describe synthesis and its desinsection of pyrazole formylamine derivate Activity: when 0.1mg/L concentration, 26 (R of compound1=Me, R2=CH3,R3=H), 27 (R1=Cl, R2=CH3,R3=H), 28 (R1 =Cl, R2=CH2CH=CH2,R3=Cl) and 29 (R1=Cl, R2=CH (CH3)2,R3=Cl) diamondback moth lethality is greater than 90%, and compound 26 in 0.05mg/L and 0.025mg/L concentration to the insecticidal activity of diamondback moth still 92% and 78%, it is excellent In reference material Rynaxypyr (75% and 51%).
Hong Yu etc. [organic chemistry, 2017 (11): 233-239] describes the pyrazole carboxamides with hepta-fluoroiso-propyl Close the synthesis and its insecticidal activity of object: in 500mg/L concentration, 30 (R of compound1=Me, R2=2-Me), 31 (R1=Me, R2 =2,3-Me2)、32(R1=Et, R2=3-Me), 33 (R1=CH3CH(CH3)CH2,R2=2-Me) and 34 (R1=CH3CH(CH3) CH2,R2=3-Me) to mythimna separata insecticidal activity 100%, concentration is down to 100mg/L, compound 30,35 (R1=4-FC6H4,R2=2- ) and 36 (R Me1=4-ClC6H4,R2=2-Me) preventive effect is still greater than 60%, it is better than positive control Tolfenpyrad (50%).
Tang Ming etc. [fine-chemical intermediate, 2012,42 (1): 28-33] describes the adjacent formamido benzene containing pyrrazole structure The synthesis and its bioactivity of carboxamides derivatives: when 1000mg/L concentration, all test compounds are equal to mythimna separata insecticidal activity 100%；When 500mg/L concentration, 37 (R=CH of compound2CH=CH2) it is 89.29% to black bean aphid insecticidal activity, compound 38 (R=CH (CH3)2) it is 81.82% to leafhopper insecticidal activity.
Li Huanpeng etc. [modern, 2016,15 (4): 6-9] describes synthesis and its biology of pyrazoles acyl methylamine derivative Activity: when 0.1mg/L concentration, 39 (R of compound1=Cl, R2=O), 40 (R1=Me, R2=O) and 41 (R1=Cl, R2=S) it is right The preventive effect of striped rice borer is respectively 96%, 93% and 97%, is superior to positive control Rynaxypyr (91%).Li Huanpeng etc. [modern, 2016 (6): 17-20] introduce tetrafluoro propoxyl group on pyrazole ring, describe pyrazolecarboxamide compounds (42 ~44) synthesis and its insecticidal activity: when 0.05mg/L concentration, 42 (R of compound1=Cl, R2=Me), 43 (R1=Cl, R2= CH(CH3)2) and 44 (R1=Br, R2=CH (CH3)2) it is respectively 92%, 89% and 83% to the preventive effect of diamondback moth, it is superior to sun Property reference material Rynaxypyr (76%).
The quasi- exploitation N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate insecticide of the present invention.
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate, its Preparation method, pharmaceutical composition and purposes.
To solve technical problem of the invention, the invention provides the following technical scheme:
There is provided one kind N- thiazolyl -1- pyridyl group -5- as shown in structural formula I for the first aspect of technical solution of the present invention Acceptable salt on pyrazole formylamine derivate and its Pesticide Science:
R is selected from: hydrogen, deuterium, C1~C2 alkyl, C3~C4 straight chained alkyl, C3~C4 branched alkyl, C1~C2 alcoxyl carbonyl first Base, C3~C4 straight chain alkane boc methyl, C3~C4 branched alkane boc methyl, cyanogen methyl or carboxymethyl；
X is selected from: C1~C2 alkyl, C3~C4 straight chained alkyl, fluorine, chlorine, bromine, iodine, trifluoromethyl or cyano；
Y is selected from: C1~C2 alkyl, C3~C4 straight chained alkyl, fluorine, chlorine, bromine, iodine, trifluoromethyl or cyano；
Z is selected from: C1~C2 alkoxy carbonyl group, C3~C4 straight chain alkoxy carbonyl group, C3~C4 branched alkoxycarbonyl groups, 1,2,4- tri- nitrogen Azoles -1- base, imidazole radicals or cyano.
A kind of N- thiazolyl -1- pyridyl group -5- pyrazolecarboxamide that the first aspect of technical solution of the present invention also provides spreads out Biology is selected from following compounds:
There is provided N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivates for the second aspect of technical solution of the present invention Preparation method, it is characterised in that it preparation reaction it is as follows:
R is selected from: hydrogen, deuterium, C1~C2 alkyl, C3~C4 straight chained alkyl, C3~C4 branched alkyl, C1~C2 alcoxyl carbonyl first Base, C3~C4 straight chain alkane boc methyl, C3~C4 branched alkane boc methyl, cyanogen methyl or carboxymethyl；X is selected from: C1~C2 alkyl, C3~C4 straight chained alkyl, fluorine, chlorine, bromine, iodine, trifluoromethyl or cyano；Y is selected from: C1~C2 alkyl, C3~C4 straight chained alkyl, fluorine, Chlorine, bromine, iodine, trifluoromethyl or cyano；Z is selected from: C1~C2 alkoxy carbonyl group, C3~C4 straight chain alkoxy carbonyl group, C3~C4 branched alkane Oxygen carbonyl, 1,2,4- triazole -1- base, imidazole radicals or cyano.
It is 4-dimethylaminopyridine that DCC, which is dicyclohexylcarbodiimide, DMAP,；
EDCI is 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride, and HOBt is I-hydroxybenzotriazole.
The third aspect of technical solution of the present invention is to provide N- thiazolyl -1- pyridyl group -5- pyrazoles formyl of the present invention Acceptable salt and third aspect described pharmaceutical composition answering in terms of preparing insecticide on amine derivative and its Pesticide Science With.It is characterized in that insecticide is the insecticide for killing the insecticide or killing aphids of mythimna separata.
Advantageous effects:
N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate (I) of the invention is a kind of change with insecticidal activity Close object.
Specific embodiment
Following embodiment is intended to illustrate invention rather than limitation of the invention further.
Embodiment 1
N- [(4- methyl -5- carbethoxyl group thiazol-2-yl) -5- base] the bromo- 1- of -3- (3- chloropyridine -2- base) -5- pyrazoles first The preparation of amide (I a)
The bromo- 1- of 0.72g (2.4mmol) 3- (3- chloropyridine -2- base) -5- pyrazole carboxylic acid, 0.46g (2.4mmol) 1- (3- bis- Methylaminopropyl) -3- ethyl-carbodiimide hydrochloride (EDCI), 0.32g (2.4mmol) I-hydroxybenzotriazole (HOBt), After 30min is stirred at room temperature, 0.38g (2.0mmol) 4- methyl -5- ethoxy carbonyl is added in 10mL n,N-Dimethylformamide (DMF) Base thiazole -2- amine, 0.5mL triethylamine, 120 DEG C are continued to be stirred to react 4.0h, are poured into water precipitation solid, crude by column chromatography Obtain white solid N- [(4- methyl -5- carbethoxyl group thiazol-2-yl) -5- base] the bromo- 1- of -3- (3- chloropyridine -2- base) -5- pyrazoles Formamide (I a), m.p.220~222 DEG C, yield 57.3%；1H NMR (400MHz, CDCl3) δ: 1.31 (t, J=7.1Hz, 3H, CH3), 2.61 (s, 3H, CH3), 4.27 (q, J=7.0Hz, 2H, CH2), 6.95 (s, 1H, pyrazole ring-H), 7.48~8.58 (m, 3H, pyridine ring-H)；13C NMR (101MHz, CDCl3) δ: 14.27,16.92,61.02,111.84,116.73,126.08, 128.35,128.98,137.25,140.00,147.00,148.22,155.24,155.90,158.79,162.25.
Embodiment 2
The system of N- (4- ethoxycarbonymetyl thiazol-2-yl) bromo- 1- of -3- (3- chloropyridine -2- base) -5- pyrazolecarboxamide (I b) It is standby
It is prepared by 1 method of embodiment, 0.37g (2.0mmol) 4- ethoxycarbonymetyl thiazole -2- amine and 0.72g (2.4mmol) The bromo- 1- of 3- (3- chloropyridine -2- base) -5- pyrazole carboxylic acid reacts 4.0h, obtains white solid N- (4- ethoxycarbonymetyl thiazole -2- Base) the bromo- 1- of -3- (3- chloropyridine -2- base) -5- pyrazolecarboxamide (I b), m.p.147~150 DEG C, yield 40.7%；1H NMR (400MHz, CDCl3) δ: 1.26 (t, J=7.0Hz, 3H, CH3), 3.67 (s, 2H, CH2), 4.18 (q, J=7.1Hz, 2H, CH2), 6.82 (s, 1H, thiazole ring-H), 6.91 (s, 1H, pyrazole ring-H), 7.45~8.54 (m, 3H, pyridine ring-H)；13C NMR (101MHz, CDCl3) δ: 14.15,36.90,61.25,111.44,111.72,126.02,128.23,128.91,137.67, 139.67,143.50,146.99,148.35,154.83,157.07,170.21.
Embodiment 3
N- (4- tert-butyl -5- (1,2,4- triazole -1- base) thiazol-2-yl) the bromo- 1- of -3- (3- chloropyridine -2- base) -5- The preparation of pyrazolecarboxamide (I c)
0.45g (2.0mmol) 4- tert-butyl -5- (1,2,4- triazole) thiazole -2- amine and the bromo- 1- of 072g (2.4mmol) 3- (3- chloropyridine -2- base) -5- pyrazole carboxylic acid, 0.62g (3.0mmol) dicyclohexylcarbodiimide (DCC), 0.10g 4- diformazan ammonia Yl pyridines (DMAP), 80mL methylene chloride, stir 6.0h at room temperature, after column chromatography white solid N- (4- tert-butyl -5- (1, 2,4- triazole -1- bases) thiazol-2-yl) the bromo- 1- of -3- (3- chloropyridine -2- base) -5- pyrazolecarboxamide (I c), m.p.222~ 224 DEG C, yield 52.1%；1H NMR (400MHz, CDCl3) δ: 1.10 (s, 9H, 3 × CH3), 6.86 (s, 1H, pyrazole ring-H), 7.52~8.77 (m, 3H, pyridine ring-H), 8.09 (s, 1H, 1,2,4- triazole ring-H), 8.47 (s, 1H, 1,2,4- triazole rings- H)。
Embodiment 4
N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate insecticidal activity assay
1 for trying target
The black bean aphid system interior (Aphis fabae) is with the sensitive strain of semen viciae fabae seedling raising many years, if test is 3 ages in days with worm Aphid.
2 condition of culture
Condition of culture for target after examination target and test is 25 ± 5 DEG C of temperature, relative humidity 65 ± 5%, periodicity of illumination 12/12h(L/D)。
3 test medicines (raw medicine): N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate.
4 medicaments prepare raw medicine: weighing aequum with a ten thousandth electronic balance；Solvent: n,N dimethylformamide (DMF), 0.2%；Emulsifier: Tween 80,0.2%；Clear water is added and is diluted to required concentration.The general sieve of noval chemical compound insecticidal activity: test Concentration is 500mg/L.
5 test methods are referring to " pesticide bioactivity evaluates SOP ".
The general sieve of black bean aphid uses infusion process: the semen viciae fabae seedling with 3 age in days semen viciae fabae larvae aphids being cut, in prepared medical fluid Dipping takes out after 10 seconds, is inserted on the sponge for suctioning water, covers the lampshade that starts, 2 repetitions of every processing.It is disposed, is put into observation Indoor culture, is periodically observed, and death condition is checked and recorded after 72h, calculates the death rate.
6 cytotoxicities
The cytotoxicity of preferred compound: when effective component concentration is 500mg/L, after handling 72h, chemical compounds I a, I b It is respectively 95.54%, 56.04% and 67.21% to the black bean aphid death rate with I c.
N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate has good insecticidal activity, can be used as and prepares desinsection Agent is agriculturally being applied.

Claims (5)

1. can in N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate shown in a kind of chemical structural formula I and its Pesticide Science The salt of receiving:
R is selected from: hydrogen, deuterium, C1~C2 alkyl, C3~C4 straight chained alkyl, C3~C4 branched alkyl, C1~C2 alkane boc methyl, C3 ~C4 straight chain alkane boc methyl, C3~C4 branched alkane boc methyl, cyanogen methyl or carboxymethyl；
X is selected from: C1~C2 alkyl, C3~C4 straight chained alkyl, fluorine, chlorine, bromine, iodine, trifluoromethyl or cyano；
Y is selected from: C1~C2 alkyl, C3~C4 straight chained alkyl, fluorine, chlorine, bromine, iodine, trifluoromethyl or cyano；
Z is selected from: C1~C2 alkoxy carbonyl group, C3~C4 straight chain alkoxy carbonyl group, C3~C4 branched alkoxycarbonyl groups, 1,2,4- triazole- 1- base, imidazole radicals or cyano.
2. N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate described in claim 1 is selected from following compounds:
3. the preparation method of N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate described in claim 1, feature exist In its preparation reaction is as follows:
Wherein, the definition of R, X, Y and Z are as described in claim 1；
It is 4-dimethylaminopyridine that DCC, which is dicyclohexylcarbodiimide, DMAP,；
EDCI is 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride, and HOBt is I-hydroxybenzotriazole.
4. N- thiazolyl -1- pyridyl group -5- pyrazole formylamine derivate of any of claims 1 or 2 is in preparing insecticide Using.
5. application as claimed in claim 4, it is characterised in that insecticide is the insecticide of killing aphids.
CN201910587127.0A 2019-07-01 2019-07-01 N-thiazolyl-1-pyridyl-5-pyrazolecarboxamide derivatives and application thereof Active CN110272413B (en)

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CN105061396A (en) * 2015-08-13 2015-11-18 南阳师范学院 Amide derivative and preparation method thereof

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CN101589030A (en) * 2007-01-26 2009-11-25 巴斯夫欧洲公司 The 3-amino-1 that is used for combating animal pests, 2-benzisothiazole compound ii
CN104650064A (en) * 2014-12-17 2015-05-27 南开大学 Aminothiazole carboxylic acid derivatives as well as preparation method and application thereof
CN105061396A (en) * 2015-08-13 2015-11-18 南阳师范学院 Amide derivative and preparation method thereof

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