CN119591556A - N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compound and preparation and application thereof - Google Patents
N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compound and preparation and application thereof Download PDFInfo
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Abstract
本发明涉及一类新的化合物及其制备方法和应用，具体涉及N,N‑二取代‑4‑(5‑(三氟甲基)‑1,2,4‑噁二唑‑3‑基)苯甲酰胺类化合物及其制备方法与应用。所述N，N‑二取代‑4‑(5‑(三氟甲基)‑1,2,4‑噁二唑‑3‑基)苯甲酰胺类化合物的结构式如式I所示：；式Ⅰ其中，R1选自甲氧基或苯基；R2选自4‑甲基苯基、4‑甲基苄基、4‑甲氧基苯基、4‑甲氧基苄基、4‑氯苄基、4‑溴苄基、3‑三氟甲基苯基或4‑三氟甲基苄基。本发明化合物尤其对葡萄座腔菌（Botryosphaeria dothidea）和瓜果腐霉菌（Pythium aphanidermatum）显示出较好的抗真菌活性，部分与上市药物氟唑菌酰胺相当。本发明化合物将为抗真菌药物的研发提供更多选择，具有广泛的应用前景。The present invention relates to a new class of compounds and preparation methods and applications thereof, and specifically to N,N-disubstituted-4-(5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl)benzamide compounds and preparation methods and applications thereof. The structural formula of the N,N-disubstituted-4-(5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl)benzamide compounds is shown in Formula I: ; Formula I wherein R 1 is selected from methoxy or phenyl; R 2 is selected from 4-methylphenyl, 4-methylbenzyl, 4-methoxyphenyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-bromobenzyl, 3-trifluoromethylphenyl or 4-trifluoromethylbenzyl. The compounds of the present invention particularly show good antifungal activity against Botryosphaeria dothidea and Pythium aphanidermatum , and some of them are comparable to the marketed drug fluopyrabacteramide. The compounds of the present invention will provide more options for the research and development of antifungal drugs and have broad application prospects.
Description
Technical Field
The invention relates to a novel compound, a preparation method and application thereof, in particular to an N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compound, and a preparation method and application thereof.
Background
In the middle of the 20 th century, the influence and scale of fungal diseases of crops are continuously increased, and the fungal diseases pose serious threats to the production and safety of rice, corn, wheat, soybean and other necessary grains. Crop losses due to plant disease and pest damage are estimated to be up to $220 billion annually worldwide. In order to reduce the loss caused by plant fungal diseases, pesticides are widely used to protect crops, and various chemical bactericides are widely used. However, widespread use of bactericides also causes problems with resistance, toxicity, pesticide residues and the like. Therefore, the development of new efficient, low-toxicity, environmentally friendly compounds to replace bactericides with resistance problems is a long-standing major challenge.
The amide compounds have wide application in the field of plant source fungus resistance, have been commercialized for more than 30 varieties for decades, and all the succinic dehydrogenase inhibitor bactericides in the bactericides on the market at present have amide structures. In recent years, heterocyclic compounds have been widely used in the fields of agricultural chemicals, medicines and the like due to their characteristics of good selectivity, high activity, small amount, environmental friendliness and the like. As an important five-membered heterocyclic compound containing N, O, the oxadiazole compound shows various biological activities, and as many documents report that trifluoromethyl oxadiazole derivatives have the effect of preventing and killing plant pathogenic microorganisms, particularly fungi. Therefore, the development of the novel oxadiazole compound with the amide skeleton has important significance.
Disclosure of Invention
The invention aims to provide N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compounds, and a preparation method and application thereof.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazol-3-yl) benzamide compounds have the structural formula shown in formula I:
Wherein R 1 is selected from methoxy or phenyl, R 2 is selected from 4-methylphenyl, 4-methylbenzyl, 4-methoxyphenyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-bromobenzyl, 3-trifluoromethylphenyl or 4-trifluoromethylbenzyl.
Further, the N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazol-3-yl) benzamide compound is selected from the group consisting of compounds I-1, I-2, I-3, I-4, I-5 and I-6, and the structural formulas of the I-1, I-2, I-3, I-4, I-5 and I-6 are as follows:
the preparation method of the N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compound has the following reaction formula:
Wherein R 1 is selected from methoxy or phenyl, R 2 is selected from 4-methylphenyl, 4-methylbenzyl, 4-methoxyphenyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-bromobenzyl, 3-trifluoromethylphenyl or 4-trifluoromethylbenzyl. The amounts of the respective reaction raw materials may be referred to those known to those skilled in the art.
The invention also provides application of the N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compound in preventing and controlling plant pathogenic fungi.
Preferably, the plant pathogenic fungus is Phytospora viticola (Botryosphaeria dothidea) or Pythium aphanidermatum (Pythium aphanidermatum).
The invention also provides a bactericide which contains at least one of the N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazol-3-yl) benzamide compounds with a bactericidal effective dose and optionally contains auxiliary materials.
Preferably, the bactericide is at least one of emulsifiable concentrate, suspending agent, wettable powder, granule, water aqua, mother solution or mother powder.
The invention has the beneficial effects that:
(1) The N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compound is designed and synthesized by taking amide as a framework, taking 4- (5- (trifluoromethyl) -1,2, 4-oxadiazole as an acid part of the amide and taking a hydrophobic benzene ring as an amine part, has novel molecular structure and clear chemical structural characteristics, and has a good effect on preventing and treating Botrytis cinerea (Botryosphaeria dothidea) and melon and fruit mould (Pythium aphanidermatum) because the N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compound is connected with the N, N-disubstituted amine group and the 5-trifluoromethyl oxadiazole benzoic acid through amide bonds.
(2) The preparation method of the compound is simple and convenient, the raw materials are easy to obtain, and the reaction conditions are easy to control. For example, in the step of synthesizing N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compounds, the product is obtained through column chromatography.
(3) The compound provided by the invention has good crop safety, can be developed into a novel plant bactericide, and is used for preventing and controlling plant pathogenic fungi in the agricultural or forestry field.
Detailed Description
In order that the above-recited objects, features and advantages of the present invention will become more apparent, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways other than those described herein, and persons skilled in the art will readily appreciate that the present invention is not limited to the specific embodiments disclosed below.
The procedures and methods not described in detail in the examples below are conventional methods well known in the art, and the reagents used in the examples are all analytically or chemically pure and are either commercially available or prepared by methods well known to those of ordinary skill in the art. The following examples all achieve the object of the invention.
The preparation method of the N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compound in the embodiment of the invention has the following reaction formula:
Example 1
Preparation of N-phenyl-N- (4-methoxybenzyl) -4- (5- (trifluoromethyl) -1,2, 4-oxadiazol-3-yl) benzamide compound:
(1) Dissolving 4-cyanobenzoic acid (0.034 mol) in 50mL of absolute ethyl alcohol and 20mL of water, stirring uniformly, adding absolute sodium carbonate (0.0506 mol), hydroxylamine hydrochloride (0.0626 mol) and 8-hydroxyquinoline (0.0017 mol) under stirring, heating the reaction solution to reflux temperature for reacting for 5 hours, monitoring the raw materials by TLC to react completely, cooling to room temperature, decompressing to remove ethanol, filtering out precipitated solid, adjusting pH to 5-6, stirring for 0.5h, filtering the solid again, washing with distilled water, and drying in vacuum at 60 ℃ to obtain a white solid intermediate 1;
(2) Placing the intermediate 1 into a 250mL single-port bottle, adding 60mL of dry tetrahydrofuran, cooling to 0-5 ℃ in an ice bath, dissolving trifluoroacetic anhydride (0.0408 mol) in 60mL of tetrahydrofuran, diluting and slowly dripping to a reaction liquid, removing the ice bath, stirring for 5h, monitoring the raw materials by TLC to react completely, concentrating under reduced pressure to obtain a solid, adding distilled water, stirring for 2h, filtering out the solid, and drying at 60 ℃ in vacuum to obtain an off-white solid intermediate 2, namely 4- (5- (trifluoromethyl) -1,2, 4-oxadiazol-3-yl) benzoic acid;
(3) Placing the intermediate 2 into a dry reaction bottle, adding thionyl chloride, heating to reflux temperature, stirring for 3h, cooling to room temperature, and concentrating under reduced pressure to obtain a crude product of the intermediate 3, namely 4- (5- (trifluoromethyl) -1,2, 4-oxadiazol-3-yl) benzoyl chloride. Wherein, the intermediate 3 should be used at present;
(4) In a dry reaction bottle, adding N-phenyl-1- (4-methoxyphenyl) ethylamine equivalent to the intermediate 3 and triethylamine equivalent to 1.5 times, dissolving the intermediate 3 in dichloromethane uniformly, stirring and dripping the mixture into a reaction liquid under ice bath, and reacting for 3-8 hours. TLC monitoring the reaction completion of the starting material, washing the organic layer with water (10 mL. Times.3), washing with saturated brine (10 mL. Times.3), drying, suction-filtering, concentrating under reduced pressure to remove dichloromethane to obtain crude product, and purifying with chromatography column (eluent petroleum ether: ethyl acetate=20:1) to obtain the target compound I-1. The yield thereof was found to be 67.5%.
I-1 pale yellow oily matter .1H NMR(600MHz,CDCl3)δ1.52(d,J＝7.2Hz,3H,CH3),3.82(s,3H,OCH3),6.39(s,1H,CH),6.63(s,2H,C6H4OMe 3,5-H),6.85(d,J＝8.6Hz,2H,C6H4OMe 2,6-H),7.11–7.04(m,3H,C6H5 3,4,5-H),7.23(d,J＝8.2Hz,2H,C6H52,6-H),7.37(d,J＝7.8Hz,2H,C6H4-oxadiazole 3,5-H),7.86(d,J＝7.9Hz,2H,C6H4-oxadiazole 2,6-H).HRMS：HR-MS(ESI):m/z calcd for C25H20F3N3O3[M+H]+468.1530,found 468.1512.
Example 2
Steps (1) - (4) are the same as in example 1, wherein in step (4), N-phenyl-1- (4-methoxybenzyl) ethylamine is used to replace N-phenyl-1- (4-methoxyphenyl) ethylamine in example 1, and the target compound I-2 is obtained. The yield thereof was found to be 72.1%.
I-2 pale yellow oily matter .1H NMR(600MHz,CDCl3)δ1.30(d,J＝6.7Hz,3H,CH3),2.72(dd,J＝13.5,7.6Hz,1H,CH2),3.24(dd,J＝12.9,7.6Hz,1H,CH),3.81(s,3H,OCH3),4.93(d,J＝4.8Hz,1H,CH),6.82(s,2H,C6H4OMe 3,5-H),6.87(d,J＝8.4Hz,2H,C6H4OMe 2,6-H),7.14(d,J＝6.7Hz,3H,C6H5 3,4,5-H),7.21(d,J＝7.2Hz,2H,C6H5 2,6-H),7.29(d,J＝7.8Hz,2H,C6H4-oxadiazole 3,5-H),7.85(d,J＝7.5Hz,2H,C6H4-oxadiazole 2,6-H).HRMS：HR-MS(ESI):m/z calcd for C26H22F3N3O3[M+H]+482.1686,found 482.1696.
Example 3
Steps (1) - (4) are the same as in example 1, wherein in step (4), N-phenyl-1- (4-methoxyphenyl) ethylamine in example 1 is replaced with N-phenyl-1- (4-bromobenzyl) ethylamine to obtain the target compound I-3. The yield thereof was found to be 73.2%.
I-3 pale yellow oily matter ,1H NMR(600MHz,CDCl3)δ1.30(d,J＝6.8Hz,3H,CH3),2.72(dd,J＝13.7,7.8Hz,1H,CH2),3.26(dd,J＝13.3,7.6Hz,1H,CH2),4.95(d,J＝5.8Hz,1H,CH),6.82(d,J＝5.6Hz,2H,C6H4Br 2,6-H),7.21–7.12(m,5H,C6H5),7.28(d,J＝7.9Hz,2H,C6H4Br 3,5-H),7.45(d,J＝8.1Hz,2H,C6H4-oxadiazole 3,5-H),7.86(d,J＝7.8Hz,2H,C6H4oxadiazole 2,6-H).HRMS：HR-MS(ESI):m/z calcd for C25H19BrF3N3O2[M+H]+530.0686,found 530.0692.
Example 4
Steps (1) - (4) are the same as in example 1, wherein in step (4), N-methoxy-1- (4-nitrobenzyl) ethylamine is used to replace N-phenyl-1- (4-methoxyphenyl) ethylamine in example 1, and the target compound I-4 is obtained. The yield thereof was found to be 65.0%.
I-4 pale yellow oily matter ,1H NMR(600MHz,CDCl3)δ1.48(d,J＝6.7Hz,3H,CH3),2.98–2.82(m,1H,CH2),3.27(dd,J＝13.5,9.4Hz,1H,CH2),3.63(s,3H,OCH3),4.66(s,1H,CH),7.38(m,4H,C6H4NO2 2,6-H,C6H4-oxadiazole 3,5-H),8.10–8.05(m,2H,C6H4-oxadiazole 2,6-H,),8.14(dd,J＝8.4,3.3Hz,2H,C6H4NO2 3,5-H).HRMS：HR-MS(ESI):m/z calcd for C20H17F3N4O5[M+H]+451.1224,found 451.1234.
Example 5
Steps (1) - (4) are the same as in example 1, wherein in step (4), N-phenyl-1- (4-methoxyphenyl) ethylamine in example 1 is replaced with N-phenyl-1- (4-trifluoromethylphenyl) ethylamine to obtain the target compound I-5. The yield thereof was found to be 66.7%.
I-5 pale yellow oily matter ,1H NMR(600MHz,CDCl3)δ1.58(d,J＝7.2Hz,3H,CH3),6.41(d,J＝6.6Hz,1H,CH),6.67(s,2H,C6H4CF3 2,6-H),7.12(dt,J＝19.7,6.9Hz,3H,C6H53,4,5-H),7.38(d,J＝8.3Hz,2H,C6H4CF3 3,5-H),7.48(d,J＝8.0Hz,2H,C6H5 2,6-H),7.60(d,J＝8.2Hz,2H,C6H4-oxadiazole 3,5-H),7.88(d,J＝8.3Hz,2H,C6H4-oxadiazole2,6-H).HRMS：HR-MS(ESI):m/z calcd for C25H17F6N3O2[M+H]+506.1298,found506.1308.
Example 6
Steps (1) - (4) are the same as in example 1, wherein in step (4), N-phenyl-1- (4-methoxyphenyl) ethylamine in example 1 is replaced with N-phenyl-1- (4-chlorobenzyl) ethylamine to obtain a target compound I-6. Yield 73.1%
I-6 pale yellow oily matter .1H NMR(600MHz,CDCl3)δ1.31(d,J＝6.8Hz,3H,CH3),2.74(dd,J＝13.7,7.7Hz,1H,CH2),3.28(dd,J＝13.3,7.6Hz,1H,CH2),4.95(d,J＝5.8Hz,1H,CH),6.82(d,J＝5.5Hz,2H,C6H4Cl 2,6-H),7.16(d,J＝7.0Hz,3H,C6H53,4,5-H),7.23(d,J＝7.6Hz,2H,C6H4Cl 3,5-H),7.29(t,J＝9.0Hz,4H,C6H5 2,6-H,C6H4-oxadiazole 3,5-H),7.86(d,J＝7.8Hz,2H,C6H4-oxadiazole 2,6-H).HRMS：HR-MS(ESI):m/z calcd for C25H19ClF3N3O2[M+H]+486.1191,found 486.1201.
Example 7
Sterilization Activity (ex vivo) experiment
The plant fungi used in this example were Portugal fungus (Botryosphaeria dothidea) and Pythium aphanidermatum (Pythium aphanidermatum) stored at 4℃in the laboratory.
The culture medium is potato agarose culture medium (PDA for short). The PDA culture medium formula comprises 200g of potato (peeled), 20g of glucose, 15g of agar and 1000mL of distilled water, wherein the PDA culture medium is prepared by cleaning and peeling the potato, weighing 200g of potato, cutting into small pieces, adding water, boiling for 20-30min, puncturing by a glass rod, filtering by eight layers of gauze, adding 20g of agar and 20g of glucose in sequence according to experimental requirements, stirring uniformly, fully dissolving, slightly cooling, supplementing water to 1000mL, sub-packaging, sterilizing at 121 ℃ for 30min, and cooling for later use.
The experimental method adopts a hypha growth rate method and comprises the following steps:
(1) Firstly, culturing the plant fungi on a PDA plate at 25 ℃ for about 3-6 days for standby;
(2) Heating PDA culture medium to dissolve, cooling to 45-50deg.C, proportionally adding 10 μl of 20mg/mL compound to be tested to obtain culture medium containing 100 μg/mL liquid medicine, and respectively pouring into culture dish for cooling;
(3) Taking circular fungus cakes (with the diameter of 0.5 cm) from the edge of hypha of each strain cultivated for 6d (the growing condition is as consistent as possible) by using a puncher through aseptic operation procedures, picking the circular fungus cakes to the center of a medicine-containing flat plate by using an inoculating needle, and then inverting a culture dish into an incubator for cultivation;
(4) Observing and measuring the growth condition of hyphae at different times after treatment, measuring the diameter by adopting a crisscross method, processing data, and calculating the inhibition rate;
Each treatment was repeated 3 times.
The test results are shown in Table 1.
TABLE 1 inhibition of Compound I-1~I-6 at a concentration of 100mg/mL for different fungi (%)
Given the general inhibitory activity of some of the target compounds against Puccinia (Botryosphaeria dothidea) and Pythium aphanidermatum (Pythium aphanidermatum), it can be seen from Table 1 that compound I-3 has optimal inhibitory activity against Puccinia (Botryosphaeria dothidea) and Pythium aphanidermatum (Pythium aphanidermatum).
The N, N-disubstituted-4- (5- (trifluoromethyl) -1,2, 4-oxadiazole-3-yl) benzamide compound has obvious structural difference and clear chemical structural characteristics, and has good effects on preventing and treating the Botrytis cinerea (Botryosphaeria dothidea) and the aphanidermatum (Pythium aphanidermatum). The compound can be used for preventing and controlling plant fungal diseases in agriculture or forestry, and has the advantages of simple preparation method, high yield and stable product property. Has potential application value for drug development of plant pathogen resistance.
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| CN114213403A (en) * | 2021-12-17 | 2022-03-22 | 贵州大学 | 1,2,4-oxadiazole-5-carboxamide derivatives and preparation method and application thereof |
| CN114605344A (en) * | 2022-03-21 | 2022-06-10 | 西北农林科技大学 | Oxadiazole compound, preparation method and application |
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