CN105330644B - （The base of 1,2,3,4 tetrahydroquinoline 1）（Substituted pyrazolecarboxylic base）First ketone compounds and its application - Google Patents
（The base of 1,2,3,4 tetrahydroquinoline 1）（Substituted pyrazolecarboxylic base）First ketone compounds and its application Download PDFInfo
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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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
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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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- 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
- C07D401/14—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 three or more hetero rings
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Abstract
The invention discloses a kind of (base of 1,2,3,4 tetrahydroquinoline 1) (substituted pyrazolecarboxylic base) first ketone compounds and its application.The structural formula of (base of 1,2,3,4 tetrahydroquinoline 1) (substituted pyrazolecarboxylic base) the first ketone compounds is as shown in Formulas I or Formula II.Compound shown in Formulas I or Formula II provided by the invention can suppress the mycelial growth of the phytopathogen.(base of 1,2,3,4 tetrahydroquinoline 1) (substituted pyrazolecarboxylic base) first ketone compounds provided by the invention, prepare simply, raw material is easy to get.It is inhibited to phytopathogen, it is especially preferable to Valsa mali, botrytis cinerea and gaeumannomyces graminis effect, it can act as disinfectant use in agriculture, controlling plant diseases.
Description
Technical field
The present invention relates to a kind of (1,2,3,4- tetrahydroquinoline -1- bases) (substituted pyrazolecarboxylic base) first ketone compounds and its answer
With.
Background technology
World population in 2011 has broken through 7,000,000,000, and crisis in food remains significant problem of the pendulum in face of people, to ensure
The yield of grain crop, nowadays, most efficient method are the uses of chemical pesticide, and this can be not only reduced because disease, worm, crop smothering draw
The loss of the grain crop risen, and also there is certain benefit to its quality.However, as agricultural chemicals largely uses, the resistance to the action of a drug
And the problems such as environment, becomes increasingly conspicuous.Therefore, it is necessary to which to develop new, efficient, wide spectrum, environment-friendly agricultural chemicals existing commercial to substitute
Kind.
Tetrahydroquinoline and its derivative are widely present in natural plants, are reported with multi-biological activity, such as 2000
Year Urbina J.M. et al. (Bioorg.Med.Chem.2000,8,691) report, which has, suppresses mycosin synthetase activity
Property, Liu Y.M. in 2014 et al. (Eur.J.Med.Chem.2015,89,320) reports have an antitumor activity, 2014 years
Keller P.A. et al. (ACS Med.Chem.Lett., 2014,5,496) reports have an Antiparasitic Activity, 2014 years
Kitamura S. et al. (Bioorg.Med.Chem.Lett., 2014,24,1715) reports can come as ecdysone agonist
Use.
Pyrazol acid amide compounds turn into the focus of agricultural chemicals research and development in recent years, the major agricultural chemicals company such as BASF in the world, visit
Ear, first just reaching, Nissan Chemical etc. has been reported that, such as herbicide piperazine pyrazosulfuron (Nissan Chemical company), bactericide fluorine azoles bacterium acyl
Amine (BASF AG), and insecticide Rynaxypyr (Beyer Co., Ltd) (pesticide market information, 2013,12,33；World pesticide,
2011,33,10).Wherein, the annual sales amount of ryanodine receptor insecticides Rynaxypyr 2013 has broken through 1,000,000,000 dollars, is
A big hot topic in insecticide (pesticide market information, 2014,9,19) at present.By the 1,2,3,4- tetra- with excellent bioactivity
Hydrogen quinoline fragment is incorporated into pyrazolecarboxamide compounds, has no the report of its related bactericidal activity.
The content of the invention
It is an object of the invention to provide a kind of (1,2,3,4- tetrahydroquinoline -1- bases) (substituted pyrazolecarboxylic base) first ketone compounds
And its application as disinfectant use in agriculture.
(1,2,3,4- tetrahydroquinoline -1- bases) (substituted pyrazolecarboxylic base) first ketone compounds such as Formulas I provided by the present invention or
Shown in Formula II,
In Formulas I, R1For C1~C4 straight or branched alkyl, substituted or unsubstituted phenyl or 3- chloropyridine -2- bases；R2
For C1~C3 straight or branched alkyl, halogen, substituted or unsubstituted phenyl；
In Formula II, R3For C1~C4 straight or branched alkyl, substituted or unsubstituted phenyl；R4For C1~C3 straight chain
Or branched alkyl, substituted or unsubstituted phenyl.
In Formulas I, R1For methyl, the tert-butyl group, phenyl, 2- chlorphenyls or 3- chloropyridine -2- bases, R2For methyl, ethyl, propyl group,
Isopropyl, phenyl, bromine, chlorine, 4- chlorphenyls or 4- methoxyphenyls.
In Formula II, R3For methyl, the tert-butyl group, phenyl or 2- chlorphenyls, R4For methyl, propyl group, isopropyl, phenyl, 4- chlorobenzenes
Base or 4- methoxyphenyls.
Compound shown in Formulas I provided by the invention can be prepared according to reaction equation as follows：
Specific method is：
1) under the conditions of existing for solvent-free or organic solvent, compound shown in formula III and thionyl chloride react
To compound shown in formula IV；
2) under the conditions of existing for acid binding agent, compound shown in formula IV is reacted to obtain formula with 1,2,3,4- tetrahydroquinolines
Compound shown in I；
In step 1), the organic solvent can be benzene or toluene；
The temperature of the reaction can be 15~110 DEG C, and the time of the reaction can be 3~5 hours, anti-such as at 110 DEG C
Answer 3 hours；
The reaction is carried out under the conditions of existing for catalyst, and the catalyst can be DMF, described
The mol ratio of catalyst and compound shown in formula III can be 0~0.5：1.
In step 2), the organic solvent is dichloromethane, and the acid binding agent can be pyridine or triethylamine.
The temperature of the reaction can be 0~25 DEG C, and the time of the reaction can be 0.5~2 hour, such as be reacted at 25 DEG C
0.5 hour；
Compound shown in formula IV and the mol ratio of 1,2,3,4- tetrahydroquinolines are 1：1.
Compound shown in Formula II provided by the invention can be prepared according to reaction equation as follows：
Specific method is：
1) under the conditions of existing for solvent-free or organic solvent, compound and thionyl chloride are reacted to obtain shown in formula V
Compound shown in formula VI；
2) under the conditions of existing for acid binding agent, compound shown in formula VI is reacted to obtain formula with 1,2,3,4- tetrahydroquinolines
Compound shown in II；
In step 1), the organic solvent can be benzene or toluene；
The temperature of the reaction can be 15~110 DEG C, and the time of the reaction can be 3~5 hours, such as be reacted at 15 DEG C
5 hours；
The reaction is carried out under the conditions of existing for catalyst, and the catalyst is DMF, described to urge
The mol ratio of agent and compound shown in formula V can be 0~0.5：1, concretely 0.5：1；
In step 2), the organic solvent is dichloromethane, and the acid binding agent can be pyridine or triethylamine.
The temperature of the reaction is 0~25 DEG C, and the time of the reaction is 0.5~2 hour, and it is small that 2 are reacted such as at 0 DEG C
When；
Compound shown in formula VI and the mol ratio of 1,2,3,4- tetrahydroquinolines are 1：1.
In above-mentioned preparation method, compound shown in compound shown in used formula III and formula V can be by as follows
It is prepared by the method disclosed in document：1) Xu Yan, thesis for the doctorate, China Agricultural University, Beijing；2)WO2012163095A1.
Compound shown in Formulas I and Formula II provided by the invention can be used for preparing disinfectant use in agriculture.
The disinfectant use in agriculture is specially the bactericide of phytopathogen；
The phytopathogen concretely Rhizoctonia solani Kuhn, Valsa mali, botrytis cinerea, rice bakanae disease
Germ, Sclerotinia sclerotiorum and/or gaeumannomyces graminis.
Compound shown in Formulas I or Formula II provided by the invention can suppress the mycelial growth of the phytopathogen.
(1,2,3,4- tetrahydroquinoline -1- bases) (substituted pyrazolecarboxylic base) first ketone compounds provided by the invention, prepare simply,
Raw material is easy to get.It is inhibited to phytopathogen, especially to Valsa mali, botrytis cinerea and take-all
Bacterium effect is preferable, can act as disinfectant use in agriculture, controlling plant diseases.
Embodiment
Experimental method used in following embodiments is conventional method unless otherwise specified.
Material used, reagent etc., unless otherwise specified, are commercially obtained in following embodiments.
First, the preparation of compound
The preparation of Formulas I -01 and Formula II -01：
The structural formula of Formulas I -01 shown in formula I, wherein, R1For Ph, R2For Me；
In 25mL there-necked flasks, 2.02g (10mmol) 1- phenyl -3- methyl isophthalic acid H- pyrazoles -5- formic acid, 3.57g are added
(30mmol) thionyl chloride, 10mL toluene, add back flow reaction 3 hours at 110 DEG C.After the completion of reaction, excessive chlorine is removed under reduced pressure
Change sulfoxide and toluene, it is standby to add 5mL dichloromethane.
In 25mL there-necked flasks, 0.79g (10mmol) pyridine, the tetrahydroquinolines of 1.33g (10mmol) 1,2,3,4-, room temperature are added
(25 DEG C) stirrings.The dichloromethane solution of the 1- phenyl -3- methyl isophthalic acid H- pyrazoles -5- formyl chlorides of above-mentioned preparation is added dropwise thereto,
Reaction 0.5 hour, washing, depressurize precipitation, column chromatography (VEthyl acetate：VPetroleum ether=1：10) purify, obtain 3.16g yellow solids, yield
99.7%.The outward appearance and fusing point of the yellow solid product are shown in Table 1,1H H NMR spectroscopy data are shown in Table 3.
The structural formula of Formula II -01 as shown in Formula II, wherein, R3For Ph, R4For Me.
In 25mL there-necked flasks, 2.02g (10mmol) 1- phenyl -5- methyl isophthalic acid H- pyrazoles -3- formic acid, 5mL protochlorides are added
Sulfone, 0.37g (5mmol) DMF, react 5 hours at 15 DEG C.After the completion of reaction, excessive chlorination is removed under reduced pressure
Sulfoxide, it is standby to add 5mL dichloromethane.
In 25mL there-necked flasks, addition 1.01g (10mmol) triethylamine, the tetrahydroquinolines of 1.33g (10mmol) 1,2,3,4-, 0
Stirred at DEG C.The dichloromethane solution of the 1- phenyl -5- methyl isophthalic acid H- pyrazoles -3- formyl chlorides of above-mentioned preparation is added dropwise thereto, instead
Answer 2 hours, wash, depressurize precipitation, column chromatography (VEthyl acetate：VPetroleum ether=1：10) purify, obtain 2.80g yellow solids, yield
88.2%.The outward appearance and fusing point of the yellow solid product are shown in Table 2,1H H NMR spectroscopy data are shown in Table 3.
In the above method, used 1- phenyl -3- methyl isophthalic acid H- pyrazoles -5- formic acid and 1- phenyl -5- methyl isophthalic acid H- pyrroles
It is prepared by the method that azoles -3- formic acid may be referred to disclosed in following document：1) Xu Yan, thesis for the doctorate, China Agricultural University,
Beijing；2)WO2012163095A1.
According to the compound shown in above-mentioned method formula I-02~Formulas I -15 and Formula II -02~Formula II -17, Formulas I -01
The substituent of~Formulas I -15 compound, outward appearance, fusing point and yield are as shown in table 1, and the compound of Formula II -02- Formula II~17 takes
Dai Ji, outward appearance, fusing point and yield are as shown in table 2.
Outward appearance, fusing point and the yield of the compound of 1-01~Formulas I of Formulas I of table-15
Outward appearance, fusing point and the yield of the compound of 2-01~Formula II of Formula II of table-17
Compound shown in Formulas I -02~Formulas I -15 and Formula II -02~Formula II -171Institute in H H NMR spectroscopies data such as table 3
Show.
The nucleus magnetic hydrogen spectrum data of the compound of table 3
2nd, inhibitory activity of each compound to 6 kinds of phytopathogens
Target compound bactericidal activity measure is carried out using mycelial growth rate method.
It is Rhizoctonia solani Kuhn, Valsa mali, botrytis cinerea, fusarium moniliforme, Sclerotina Sclerotiorum in Winter Rape for examination strain
Core germ and gaeumannomyces graminis.
Target compound and fluopicolide active compound are weighed respectively, and it is 10000mg/L's to be configured to concentration with dimethyl sulfoxide (DMSO)
Mother liquor, the potato glucose fine jade of sterilized cooling is added to the mother liquor for moving each compound 10000mg/L of rifle absorption respectively
In fat (PDA) culture medium, after mixing, the toxic culture mediums of 50mg/L are prepared into, are poured into a diameter of 9cm culture dish, per ware
15mL, each 4 repetitions of medicament.After toxic culture medium condensation in ware, toxic PDA plate is made.With the fluorine acyl of same concentrations
Amine is comparison medicament, if dimethyl sulfoxide (DMSO) compares for solvent blank.By cultured pathogen flat board, punched along colony edge
Device is prepared into diameter 0.7cm bacteria cake, is inoculated in band medicine and blank control culture medium, is respectively placed in 25 DEG C of incubators respectively
Dark culturing.After fully being grown Deng bacterium colony in blank control, the colony diameter of each processing is measured with crossing method, takes it average
Value.
Mycelial growth inhibition rate is calculated with below equation：
The in vitro bactericidal activity data of compound are shown in Table 4.
The in vitro bactericidal activity result (inhibiting rate %) of 4 each compound of table
From table 4, it can be seen that compound provided by the invention is respectively provided with certain suppression to the 6 kinds of phytopathogens tested
System activity.Wherein, multiple compounds exceed to the inhibiting rate of Valsa mali, botrytis cinerea and gaeumannomyces graminis
80%, better than comparison medicament fluopicolide.Compound I-13, I-14, II-02, II-03, II-04, II-09, II-10, II-
11st, II-15, II-16 and II-17 to the inhibiting rate of Valsa mali more than 90%；Compound II-02, II-03, II-
07th, II-09, II-10, II-15, II-16 and II-17 to the inhibiting rate of botrytis cinerea more than 80%；Compound I-02,
I-03, I-04, I-13, I-14, II-04, II-06 and II-08 are to the inhibiting rate of gaeumannomyces graminis more than 90%.
As shown by data in table 4, compound provided by the invention is to Rhizoctonia solani Kuhn, Valsa mali, rice bakanae disease
Germ, botrytis cinerea, Sclerotinia sclerotiorum and gaeumannomyces graminis have good inhibiting effect, have and are used as bactericide
Value for above-mentioned control of plant disease.
Claims (6)
1. (1,2,3,4- tetrahydroquinoline -1- bases) (substituted pyrazolecarboxylic base) first ketone compounds shown in Formulas I,
In Formulas I, R1For methyl, the tert-butyl group, phenyl, 2- chlorphenyls or 3- chloropyridine -2- bases, R2For methyl, ethyl, propyl group, isopropyl
Base, phenyl, bromine, chlorine, 4- chlorphenyls or 4- methoxyphenyls.
2. (1,2,3,4- tetrahydroquinoline -1- bases) (substituted pyrazolecarboxylic base) first ketone compounds shown in Formula II,
In Formula II, R3For methyl, the tert-butyl group, phenyl or 2- chlorphenyls, R4For methyl, propyl group, isopropyl, phenyl, 4- chlorphenyls or
4- methoxyphenyls.
The preparation method of (1,2,3,4- tetrahydroquinoline -1- bases) (substituted pyrazolecarboxylic base) first ketone compounds 3. shown in Formulas I, including such as
Lower step：
In Formulas I, R1For methyl, the tert-butyl group, phenyl, 2- chlorphenyls or 3- chloropyridine -2- bases；R2For methyl, ethyl, propyl group, isopropyl
Base, phenyl, bromine, chlorine, 4- chlorphenyls or 4- methoxyphenyls；
1) under the conditions of existing for solvent-free or organic solvent, compound shown in formula III and thionyl chloride are reacted to obtain formula
Compound shown in IV；
In formula III and formula IV, R1And R2The same Formulas I of definition；
2) under the conditions of existing for acid binding agent, compound shown in formula IV is reacted to obtain Formulas I institute with 1,2,3,4- tetrahydroquinolines
Show compound.
The preparation method of (1,2,3,4- tetrahydroquinoline -1- bases) (substituted pyrazolecarboxylic base) first ketone compounds 4. shown in Formula II, including
Following steps：
In Formula II, R3For methyl, the tert-butyl group, phenyl or 2- chlorphenyls；R4For methyl, propyl group, isopropyl, phenyl, 4- chlorphenyls or
4- methoxyphenyls；
1) under the conditions of existing for solvent-free or organic solvent, compound and thionyl chloride shown in formula V are reacted to obtain formula VI
Shown compound；
In formula V and formula VI, R3And R4The same Formula II of definition；
2) under the conditions of existing for acid binding agent, compound shown in formula VI is reacted to obtain Formula II institute with 1,2,3,4- tetrahydroquinolines
Show compound.
5. a kind of disinfectant use in agriculture, its active component is compound described in compound described in claim 1 and/or claim 2；
The disinfectant use in agriculture is the bactericide of phytopathogen；
The phytopathogen is Rhizoctonia solani Kuhn, Valsa mali, botrytis cinerea, fusarium moniliforme, rape
Hyphal cluster germ and/or gaeumannomyces graminis.
6. application of the compound in disinfectant use in agriculture is prepared described in compound described in claim 1 and/or claim 2；
The disinfectant use in agriculture is the bactericide of phytopathogen；
The phytopathogen is Rhizoctonia solani Kuhn, Valsa mali, botrytis cinerea, fusarium moniliforme, rape
Hyphal cluster germ and/or gaeumannomyces graminis；
Compound described in compound described in claim 1 and/or claim 2 suppresses the mycelial growth of the phytopathogen.
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| CN105924397B (en) * | 2016-04-29 | 2017-11-24 | 河南省农业科学院植物保护研究所 | A kind of formic acid esters pyrazole compound of 1,5 diaryl 3, Preparation method and use |
| CN113754633B (en) * | 2021-09-26 | 2023-05-05 | 中国农业大学 | 1- (6-substituted pyrimidine-4-yl) -1,2,3, 4-tetrahydroquinoline compound and preparation method and application thereof |
| CN113717155B (en) * | 2021-09-26 | 2023-03-17 | 中国农业大学 | (1, 2,3, 4-tetrahydroquinolyl) -2-substituted pyrimidineaminoacetophenone compound and preparation method and application thereof |
| CN113698344B (en) * | 2021-09-26 | 2023-03-21 | 中国农业大学 | (1,2,3,4-tetrahydroquinoline- (thio) carbonyl) substituted sulfonyl hydrazine compound and preparation method and application thereof |
| CN115124463B (en) * | 2022-07-01 | 2023-11-28 | 浙江工业大学 | Substituted quinoline compound and preparation method and application thereof |
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| JPS61227506A (en) * | 1985-04-01 | 1986-10-09 | Nippon Tokushu Noyaku Seizo Kk | Carbamoylimidazole, intermediate and, production thereof and herbicide, agricultural and horticultural fungicide |
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