CN102746282B - N-5-substituted phenyl-2-furoyl compounds, preparation method and application thereof - Google Patents
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Abstract
The invention discloses N-5-substituted phenyl-2-furoyl compounds, a preparation method and application thereof. The general structural formula of the compounds is shown as formula I. The preparation method comprises: in the presence of SOCl2 and a solvent, reacting the compound shown in formula II with the compound shown in formula III, thus obtaining the N-5-substituted phenyl-2-furoyl compounds. The compounds have an obvious control effect on Cucumber Fusarium wilt and pepper phytophthora blight, and can be applied in vegetable disease control. The formula I is shown in the description.
Description
Technical field
The present invention relates to N-5-substituted-phenyl-2-furancarbonyl compounds and preparation method thereof and application.
Background technology
Nitrogen heterocyclic ring structure has played consequence in medicament research and development process, particularly pyrazoles and triazole species 5-member heterocyclic ring containing nitrogen, show good biological activity (Clemens, L.Pyrazole chemistry in crop protection.Heterocycles, 2007,71 (7), 1467-1502; Al-Masoudi I.A., Al-Soud Y.A., Al-Salihi N.J., Al-Masoudi N.A.1,2,4-Triazoles:synthetic approaches and pharmacological importance.Chem.Heterocycl Compds., 2006,42 (11), 1377-1404; Moulin A., Bibian M., Blayo A.-L., El Habnouni S., Martinez J., Fehrentz, J.-A.Synthesis of 3,4,5-Trisubstituted-1,2,4-triazoles.Chem Rev., 2010,110 (4), 1809-1827.).Some commercial pesticide species containing such heterocycle or the active fine compound structure with potentiality to be exploited in table 1, are summed up.Can find out from activity, this class formation has the activity of good and wide spectrum, and action target is various; Can find out from compound structure, majority of compounds is N-alkylation or arylation pyrazoles or triazole derivative, acyl group class more rare, and only having PH 60-42 and triaguron is pyrazoles and the triazole derivative of N-acyl group class.
Furan nucleus has aromaticity, sp in its Sauerstoffatom
2there are a pair of lone-pair electron in track, can participate in the formation of hydrogen bond in organism, increases the interaction between giving and accepting, and contributes to improve biological activity.5-phenyl-2-furan nucleus is present in natural product widely, and no matter its natural product or the derivative of synthetic, all has biological activity widely.
Table 1, containing the commercialization agricultural chemicals of pyrazoles, triazole ring
Summary of the invention
The object of this invention is to provide a kind of N-5-substituted-phenyl-2-furancarbonyl compounds and preparation method thereof and application.
The invention provides N-5-substituted-phenyl-2-furancarbonyl compounds, is also N-5-substituted-phenyl-2-furancarbonyl pyrazoles or triazole derivative, and its general structure is suc as formula shown in I,
(formula I)
In described formula I, R
1the position of substitution can be in 2,3,4 or 6 of phenyl ring, can be monosubstituted, can be also disubstituted phenyl, R
1be selected from hydrogen, halogen, nitro, hydroxyl, the total number of carbon atoms is at least one in the alkyl of 1-4 and alkoxyl group that the total number of carbon atoms is 1-4, preferably hydrogen, fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, the tertiary butyl, methoxyl group, oxyethyl group, positive propoxy, at least one in isopropoxy and nitro, more preferably the methoxyl group of 4 replacements, the chlorine of 2 replacements, the chlorine of 3 replacements, the chlorine of 4 replacements, the methyl of 4 replacements, the fluorine of 2 replacements, the fluorine of 3 replacements, the fluorine of 4 replacements, 2, the difluoro that 4-position replaces, 2, the difluoro of 6 replacements, at least one in the nitro of the nitro of 2 replacements and 3 replacements, X is carbon or nitrogen.
Shown in the above-mentioned formula I of preparation provided by the invention, the method for compound, comprises the steps: at SOCl
2with solvent exist condition under, compound shown in formula II (pyrazoles or triazole) is mixed and is reacted with compound shown in formula III (5-substituted-phenyl furans-2-formic acid), react the complete compound shown in described formula I that obtains,
(formula II)
Described R
1be selected from hydrogen, halogen, nitro, hydroxyl, the total number of carbon atoms is at least one in the alkyl of 1-4 and alkoxyl group that the total number of carbon atoms is 1-4, preferably hydrogen, fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, the tertiary butyl, methoxyl group, oxyethyl group, positive propoxy, at least one in isopropoxy and nitro, more preferably the methoxyl group of 4 replacements, the chlorine of 2 replacements, the chlorine of 3 replacements, the chlorine of 4 replacements, the methyl of 4 replacements, the fluorine of 2 replacements, the fluorine of 3 replacements, the fluorine of 4 replacements, 2, the difluoro that 4-position replaces, 2, the difluoro of 6 replacements, at least one in the nitro of the nitro of 2 replacements and 3 replacements, X is carbon or nitrogen.
This reaction equation is as follows:
In aforesaid method, described solvent is particularly aliphatics of inert organic solvents, the hydrocarbon of the optional halo of alicyclic or aromatics, specifically can be selected from benzene, toluene, dimethylbenzene, chlorobenzene, dichlorobenzene, sherwood oil, hexane, hexanaphthene, methylene dichloride, chloroform, tetracol phenixin, ether, diisopropyl ether, dioxan, tetrahydrofuran (THF), glycol dimethyl ether, ethylene glycol diethyl ether, acetone, butanone, mibk, acetonitrile, propionitrile, butyronitrile, N, dinethylformamide, N, N-N,N-DIMETHYLACETAMIDE, N-methyl-formylaniline, N-Methyl pyrrolidone, HMPA, methyl acetate, ethyl acetate, dimethyl sulfoxide (DMSO), methyl alcohol, ethanol, n-propyl alcohol, Virahol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, at least one in diethylene glycol monomethyl ether and diethylene glycol monoethyl ether, preferably benzene, at least one in toluene and chlorobenzene.
In described reactions steps, temperature is 0 DEG C-160 DEG C, and preferably 20 DEG C-120 DEG C, more preferably 80 DEG C, the time is 3-9 hour, preferably 4-6 hour, more preferably 3 hours.
Described SOCl
2, compound shown in compound shown in described formula II and formula III molar ratio be 1-5: 1-1.5: 1-1.5, preferably 2-3: 1-1.2: 1-1.2, more preferably 3: 1: 1.The consumption of solvent is as the criterion with complete solubilizing reaction thing.
The application of compound shown in the formula I that the invention described above provides in the biological control of Plant diseases, and as the biological control agents of plant diseases of activeconstituents, also belong to protection scope of the present invention taking compound shown in this formula I.Described Plant diseases is cucumber fusarium axysporum, Cucumber Target Leaf Spot, capsicum epidemic disease and/or rice sheath blight disease.
N-5-substituted-phenyl-2-furancarbonyl compounds provided by the invention; its preparation method is simple, productive rate is high; cucumber fusarium axysporum, Cucumber Target Leaf Spot, capsicum epidemic disease and rice sheath blight disease disease are all had to good prevention effect; especially cucumber fusarium axysporum and capsicum epidemic disease are had to obvious prevention effect, can be used as disinfectant use in agriculture and be applied to the control of vegetable disease.
Embodiment
Below in conjunction with specific embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.Described method is ordinary method if no special instructions.Described material all can obtain from open commercial sources if no special instructions.
In the method for preparing N-5-substituted-phenyl-2-furancarbonyl compounds provided by the invention, as compound shown in the formula III of initial reactant, all can prepare and obtain by currently known methods, if 5-substituted-phenyl-2-furancarboxylic acid can be starting raw material from 2-furancarboxylic acid, make through the reaction of Meerwein arylation, referring to following document (Krutosikova, A.; Kovac, J.; Rentka, J.; Cakrt, M.Furan derivatives.XLIX.Transmission of polar effects in 4-substituted-5-phenyl-2-furancarboxylic acids.Collection Czechoslov Chemical Communication, 1974,39 (3), 767-771), concrete preparation method is as follows: 0.05mol substituted aniline is dissolved in 10mL hot water, and under stirring, adding 15mL concentration expressed in percentage by volume is 36% concentrated hydrochloric acid, then adds 15g trash ice.At the 0-5 DEG C of 15mL aqueous solution that drips wherein 0.05mol Sodium Nitrite, continue to stir 10min, add wherein 25mL acetone soln and the 1.5g cupric chloride of 0.05mol furancarboxylic acid, in 25-30 DEG C of reaction 6h.The aqueous ethanolic solution recrystallization that suction filtration is 50% by concentration expressed in percentage by volume obtains 5-substituted-phenyl-2-furancarboxylic acid.
Embodiment 1
1) prepare the 5-of compound shown in formula III (4-chloro-phenyl-)-2-furancarboxylic acid (R
1be the chlorine of 4 replacements):
(formula III)
6.4g (0.05mol) p-Chlorobenzoic acid amide is dissolved in to the concentrated hydrochloric acid that 5mL water and 15mL concentration expressed in percentage by volume are 36%, add again 15g trash ice, 0 DEG C drips the 15mL aqueous solution of 3.45g (0.05mol) Sodium Nitrite, after stirring 10min, add 25mL acetone soln and the 1.5g cupric chloride of 5.6g (0.05mol) furancarboxylic acid, after 25 DEG C of reaction 6h, suction filtration, the aqueous ethanolic solution recrystallization that is 50% by concentration expressed in percentage by volume, obtain 5-shown in 3.9g formula III (4-chloro-phenyl-)-2-furancarboxylic acid, outward appearance is light yellow solid, m.p.:198-199 DEG C, yield 35%.
2) N-shown in preparation formula I (5-(4-chloro-phenyl-)-2-furancarbonyl) pyrazoles
In the 25mL there-necked flask that prolong is housed, add 0.05mol step 1) prepare compound 5-shown in gained formula III (4-chloro-phenyl-)-2-furancarboxylic acid, 0.15mol thionyl chloride and 20mL solvent benzol, after 80 DEG C of back flow reaction 3h, react complete, remove excessive thionyl chloride and solvent benzol.Resistates is dissolved in 20mL methylene chloride, then adds compound pyrazoles shown in 0.05mol formula II (X is C), and back flow reaction 4h, obtains crude product, and product, through recrystallizing methanol, obtains sterling, yield 83.5%, fusing point: 174-175 DEG C.
The structure detection result of this product is as follows:
1H?NMR(DMSO-d
6，δH?ppm)：6.71(dd，J＝2.81，1.52Hz，1H，PyH)，7.38(d，J＝3.81Hz，1H，FuH)，7.59-7.62(m，2H，ArH-Fu)，7.91-7.94(m，2H，ArH-Fu)，8.03(d，J＝1.52Hz，1H，PyH)，8.13(d，J＝3.81Hz，1H，FuH)，8.60(d，J＝2.79Hz，1H，PyH)。IR(cm
-1)：3154.9，3131.4，1678.4，1515.9，1475.0，1417.2，1383.9，1346.3，1266.1，1193.9，1086.7，1040.3，1013.3。Ultimate analysis (measured value/calculated value): C:61.73/61.66, H:3.52/3.33, N:10.51/10.27.
As from the foregoing, this product structure is correct, is compound N shown in formula I-(5-(4-chloro-phenyl-)-2-furancarbonyl) pyrazoles, wherein, and R
1be the Cl of 4 replacements, X is C, and this compound number is I-A1.
According to the identical method of upper preparation Compound I-A1, only by X and R in compound shown in formula II and formula III
1according to replacing shown in table 2, obtain product shown in corresponding formula I, numbering is followed successively by I-A2-I-A13, I-B1-I-B11.The outward appearance of above-claimed cpd and productive rate are all listed in table 2, and nucleus magnetic hydrogen spectrum detected result is all listed in table 3.As from the foregoing, it is correct that above-mentioned numbering is followed successively by the compound structure of I-A2-I-A13, I-B1-I-B11, is compound shown in formula I.
The physical constant data of table 2, I-A1---I-B11
The proton nmr spectra data of table 3, I-A1---I-B11
The agricultural bactericidal activity of embodiment 2, N-5-substituted-phenyl-2-furancarbonyl compounds
Embodiment 1 is prepared to compound that institute's call number is followed successively by I-A1-I-A13, I-B1-I-B11 and prevents and treats the live body microscreen test of vegetables Major Diseases.Concrete test method is as follows:
For trying pathogen species: cucumber fusarium axysporum (Fusarium Oxysporum), Cucumber Target Leaf Spot (Corynespora Cassiicola), capsicum epidemic disease (Phytophthora Capsici), rice sheath blight disease (Rhizoctonia Solanii).(Baoju?Li，Huizhu?Yuan，Jichao?Fang，Liming?Tao，Qingchun?Huang，Xuhong?Qian?and?Zhijin?Fan，Recent?progress?of?highly?efficient?in?vivo?biological?screening?for?novel?agrochemicals?in?China，Pest?Management?Science，2010，66(3)，238-247)。
For studying thing: cucumber (Cucumis sativus L.), kind is the close thorn in Xintai City, 1 leaf period cucumber seedling; Capsicum (Capsicum frutescens), kind is middle green pepper No. 6,4 leaf phase Hot Pepper Seedlings.
Laboratory sample: I-A1-I-A13, I-B1-I-B11 compound and contrast medicament are all mixed with to the experimental concentration of 500 μ g/mL with acetone, contrast medicament is selected respectively procymidone, thiophanate_methyl, m-tetrachlorophthalodinitrile and jingganmycin.3 repetitions are established in all processing, repeat 10 young plants, random alignment in greenhouse at every turn.
Climatological data: duration of test is taking fine as main, and temperature of shed is minimum is 18 DEG C, is up to 30 DEG C, and medial temperature is 24 DEG C, and relative humidity remains on more than 80%.
Soil information: soil type: the peat composed of rotten mosses, vermiculite, chicken manure, mass ratio is 25: 12: 1.
Dispenser, vaccination ways: first carry out dispenser, in fine day morning by the reagent agent preparing by experimental concentration and contrast medicament application on crop, prevent and treat rice sheath blight disease, Cucumber Target Leaf Spot employing spray pesticide mode, after medicament is air-dry, inoculate pathogenic bacteria, cucumber fusarium axysporum, capsicum epidemic disease adopt fills with root insecticide-applying way.Then inoculate, the vaccination ways of Cucumber Target Leaf Spot bacterium adopts spore suspension spray inoculation method, and the vaccination ways of Rhizoctonia solani Kuhn adopts lawn blade face inoculation method, and cucumber fusarium axysporum germ adopts radicle inoculation method, and phytophthora capsici adopts fills with root inoculation method.After inoculation, moisturizing is cultivated.After falling ill, calculate prevention effect.
Result investigation: wait to contrast abundant morbidity " Invest, Then Investigate " lesion area, disease index, diseased plant rate, calculate preventive effect.Cucumber Target Leaf Spot, capsicum epidemic disease and rice sheath blight disease all adopt the method for classification investigation scab expanding area, and cucumber fusarium axysporum adopts diseased plant rate investigation method; Wherein, in the method for classification investigation scab expanding area, the state of an illness is divided into 5 grades, scab expanding area account for leaf area 20%, 40%, 60%, 80% and 100% be decided to be successively 1-5 level.
The compounds of this invention is prevented and treated the selection result in table 4 to vegetables Major Diseases.
Table 4, embodiment 1 gained compound are to vegetables Major Diseases control spectrum the selection result (500 μ g/mL, live body)
Note: different strains contrast medicament: a. procymidone; B. thiophanate_methyl; C. m-tetrachlorophthalodinitrile; D. jingganmycin; For the prevention effect of cucumber fusarium axysporum in diseased plant rate;
As can be seen from Table 4, I-B series compound generally has good preventive effect to capsicum epidemic disease, and wherein the preventive effect of I-B4 and I-B10 is respectively 95.36% and 95.07%, exceedes the preventive effect 93.18% of contrast sterilant procymidone.I-A1, I-A4 and I-A7 are obvious to cucumber fusarium axysporum preventive effect, are respectively 64.52%, 70.97% and 85.48%, are equivalent to or higher than the preventive effect (64.52%) of contrast medicament thiophanate_methyl; Test compound has certain preventive effect to Cucumber Target Leaf Spot and rice sheath blight disease, but with contrast medicament and differ far away.
After the disease such as target compound control cucumber, capsicum involved in the present invention, to the host plant such as cucumber, capsicum safety, occur without poisoning situation compared with blank.I-B series compound has good preventive effect to capsicum epidemic disease, and especially the preventive effect of I-B4 and I-B10 is better than contrasting sterilant procymidone, can be applied to the control of capsicum epidemic disease.I-A4 and I-A7 are obvious to cucumber fusarium axysporum preventive effect, higher than contrast medicament thiophanate_methyl, can be applied to the control of cucumber fusarium axysporum.
Claims (22)
1. substituted-phenyl-the 2-of N-5-shown in formula I furancarbonyl compounds,
In described formula I, R
1at least one in the alkoxyl group that the alkyl that to be selected from hydrogen, halogen, nitro, hydroxyl, the total number of carbon atoms be 1-4 and the total number of carbon atoms are 1-4; X is carbon or nitrogen.
2. compound according to claim 1, is characterized in that: in described formula I, and R
1be selected from least one in hydrogen, fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, the tertiary butyl, methoxyl group, oxyethyl group, positive propoxy, isopropoxy and nitro.
3. compound according to claim 2, is characterized in that: in described formula I, and R
1be selected from the fluorine of the fluorine of the methyl of the chlorine of the chlorine of the chlorine of the methoxyl group of 4 replacements, 2 replacements, 3 replacements, 4 replacements, 4 replacements, 2 replacements, 3 replacements, the fluorine, 2 of 4 replacements, at least one in difluoro, the difluoro of 2,6 replacements, the nitro of 2 replacements and the nitro of 3 replacements that 4-position replaces.
4. a method of preparing the arbitrary described compound of claim 1-3, comprises the steps: at SOCl
2with solvent exist condition under, compound shown in formula II is mixed and is reacted with compound shown in formula III, react the complete compound shown in described formula I that obtains,
Described R
1be selected from least one in hydrogen, halogen, nitro, hydroxyl, alkyl that the total number of carbon atoms is 1-4, alkoxyl group that the total number of carbon atoms is 1-4; X is carbon or nitrogen.
5. method according to claim 4, is characterized in that: described R
1be selected from least one in hydrogen, fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, the tertiary butyl, methoxyl group, oxyethyl group, positive propoxy, isopropoxy and nitro.
6. method according to claim 5, is characterized in that: described R
1be selected from the fluorine of the fluorine of the methyl of the chlorine of the chlorine of the chlorine of the methoxyl group of 4 replacements, 2 replacements, 3 replacements, 4 replacements, 4 replacements, 2 replacements, 3 replacements, the fluorine, 2 of 4 replacements, at least one in difluoro, the difluoro of 2,6 replacements, the nitro of 2 replacements and the nitro of 3 replacements that 4-position replaces.
7. according to the arbitrary described method of claim 4-6, it is characterized in that: described solvent is selected from benzene, toluene, dimethylbenzene, chlorobenzene, dichlorobenzene, sherwood oil, hexane, hexanaphthene, methylene dichloride, chloroform, tetracol phenixin, ether, diisopropyl ether, dioxan, tetrahydrofuran (THF), glycol dimethyl ether, ethylene glycol diethyl ether, acetone, butanone, mibk, acetonitrile, propionitrile, butyronitrile, N, dinethylformamide, N, N-N,N-DIMETHYLACETAMIDE, N-methyl-formylaniline, N-Methyl pyrrolidone, HMPA, methyl acetate, ethyl acetate, dimethyl sulfoxide (DMSO), methyl alcohol, ethanol, n-propyl alcohol, Virahol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, at least one in diethylene glycol monomethyl ether and diethylene glycol monoethyl ether.
8. according to the arbitrary described method of claim 4-6, it is characterized in that: in described reactions steps, temperature is 0 DEG C-160 DEG C, and the time is 3-9 hour.
9. method according to claim 8, is characterized in that: in described reactions steps, temperature is 20 DEG C-120 DEG C, and the time is 4-6 hour.
10. method according to claim 7, is characterized in that: in described reactions steps, temperature is 0 DEG C-160 DEG C, and the time is 3-9 hour.
11. methods according to claim 10, is characterized in that: in described reactions steps, temperature is 20 DEG C-120 DEG C, and the time is 4-6 hour.
12. according to the arbitrary described method of claim 4-6, it is characterized in that: described SOCl
2, compound shown in compound shown in described formula II and formula III molar ratio be 1-5:1-1.5:1-1.5.
13. methods according to claim 12, is characterized in that: described SOCl
2, compound shown in compound shown in described formula II and formula III molar ratio be 2-3:1-1.2:1-1.2.
14. methods according to claim 13, is characterized in that: described SOCl
2, compound shown in compound shown in described formula II and formula III molar ratio be 3:1:1.
15. methods according to claim 7, is characterized in that: described SOCl
2, compound shown in compound shown in described formula II and formula III molar ratio be 1-5:1-1.5:1-1.5.
16. methods according to claim 15, is characterized in that: described SOCl
2, compound shown in compound shown in described formula II and formula III molar ratio be 2-3:1-1.2:1-1.2.
17. methods according to claim 16, is characterized in that: described SOCl
2, compound shown in compound shown in described formula II and formula III molar ratio be 3:1:1.
18. methods according to claim 8, is characterized in that: described SOCl
2, compound shown in compound shown in described formula II and formula III molar ratio be 1-5:1-1.5:1-1.5.
19. methods according to claim 18, is characterized in that: described SOCl
2, compound shown in compound shown in described formula II and formula III molar ratio be 2-3:1-1.2:1-1.2.
20. methods according to claim 19, is characterized in that: described SOCl
2, compound shown in compound shown in described formula II and formula III molar ratio be 3:1:1.
The application of the arbitrary described compound of 21. claim 1-3 in the biological control of Plant diseases;
Described Plant diseases is cucumber fusarium axysporum, Cucumber Target Leaf Spot, capsicum epidemic disease and/or rice sheath blight disease.
22. biological control agents of plant diseases taking the arbitrary described compound of claim 1-3 as activeconstituents;
Described Plant diseases is cucumber fusarium axysporum, Cucumber Target Leaf Spot, capsicum epidemic disease and/or rice sheath blight disease.
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| AR110456A1 (en) * | 2016-01-13 | 2019-04-03 | Bayer Cropscience Ag | USE OF ACTIVE SUBSTANCES TO CONTROL INFECTIONS BY VIRUSES IN PLANTS |
| CN106045982B (en) * | 2016-05-31 | 2018-08-07 | 华南农业大学 | N ' -5- (substituted-phenyl) -2- furanylcarbonyl -5- propyl -1H- pyrazoles -3- Ethyl formate class compounds and its preparation method and application |
| CN106565695B (en) * | 2016-10-09 | 2019-10-29 | 华南农业大学 | A kind of 2,4- disubstituted pyrazole class compound of the ring containing oxazole and its preparation method and application |
| CN107674070B (en) * | 2017-09-19 | 2020-12-29 | 华南农业大学 | Cyanoimine thiazolidine furan carboxamide compound and preparation method and application thereof |
| CN107814791B (en) * | 2017-10-31 | 2021-07-09 | 华南农业大学 | Substituted phenyl furan formyl pyrazole compound and preparation method and application thereof |
| CN111499628B (en) * | 2020-03-27 | 2021-07-27 | 浙江工业大学 | 2-furoylamide compound and preparation and application thereof |
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