Tralopyril-triphenylphosphine derivative, and preparation method and application thereof

Abstract

The application provides a Tralopyril-triphenylphosphine derivative, a preparation method and application thereof, and belongs to the technical field of pesticide compound synthesis. The application uses Tralopyril as a parent structure, uses flexible chains with different lengths to couple and splice with a triphenylphosphine cation, synthesizes a series of new compounds, and the chemical structures are novel. The biological determination results show that in terms of nematode killing, the toxicity of some compounds to Caenorhabditis elegans is higher than that of the commercial pesticide fosted. In the root knot nematode potting activity determination, the compound 5f has higher root irrigation activity than the control agent triforine. In terms of bactericidal activity, the compounds have higher biological activity on Rhizoctonia solani, Sclerotinia sclerotiorum, Gaeumannomyces graminis and Magnaporthe oryzae, and the activity of the compounds 5b, 5c, 5d and 5f on Sclerotinia sclerotiorum is higher than that of the commercial pesticide azoxystrobin. The synthesized new compounds have high commercial prospects.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of pesticide compound synthesis, and particularly relates to a Tralopyril-triphenylphosphine derivative and a preparation method and application thereof. BACKGROUND

[0002] Plant parasitic nematodes are one of the most important pathogens of plants, and it is estimated that the economic losses caused by them worldwide each year exceed 157 billion US dollars. Currently, more than 4100 species of plant parasitic nematodes have been reported, and the nematodes that currently have a serious threat to agricultural production are root-knot nematodes (Meloidogyme), cyst nematodes (Heterodera) and Globodera. When plant parasitic nematodes invade host plants, they will destroy the cells or tissues of the host, parasitize and absorb nutrients, and interfere with the normal metabolism, growth and development of the host, thereby causing a serious reduction in crop yield or even complete loss of crops.

[0003] At present, the methods for preventing and controlling plant parasitic nematodes by non-chemical methods include crop rotation, regular fallow, soil disinfection before sowing, breeding of resistant varieties, etc. Although the cost is low, the effect is poor, and therefore chemical methods have always been the main method for controlling nematodes. However, with the increasing requirements for food safety and environmental protection, high-toxicity insecticides such as methyl bromide and dibromochloropropane are no longer suitable for the requirements of modern agricultural development, and the overuse of traditional nematocide avermectin has also led to an increase in nematode resistance. Therefore, it is an important task in the field of plant protection to find new nematocides with high efficiency, broad spectrum, novel mechanism of action, and safety to the environment and non-target organisms.

[0004] In the development and research of pesticides, natural products and their derivatives have always been an important source. Tralopyril is a 2-arylpyrrole compound synthesized by modifying the natural antibiotic Dioxapyrrolomycin, which has excellent insecticidal and miticidal activity. The product acts on the target insect mitochondria, and is an arylpyrrole insecticide with development prospects. The triphenylphosphine cation is the most common lipophilic cation, which has strong mitochondrial targeting ability. After coupling with a pharmacophore, it can penetrate the cell membrane and drive the pharmacophore to accumulate in the negatively charged inner membrane of the mitochondria. At present, the method for preparing targeted drugs by coupling triphenylphosphine cation with commercial drugs has been widely used in medicine, but there are few reports in the field of agriculture. SUMMARY

[0005] The present application aims to provide a Tralopyril-triphenylphosphine derivative and a preparation method and application thereof, so as to solve the technical problem of single structure of new nematocides.

[0006] In order to achieve the above-mentioned application purposes, the present application provides the following technical solutions:

[0007] The present application provides a Tralopyril-triphenylphosphine derivative, which has the following structural formula:

[0008]

[0009] wherein n = 3-12.

[0010] Further, the Tralopyril-triphenylphosphine derivative is selected from the following compounds of the structural formula:

[0011]

[0012] The present application also provides a preparation method of the Tralopyril-triphenylphosphine derivative, comprising the following steps:

[0013] 1) mixing bromopyrrole nitrile, ethyl bromoacetate, potassium carbonate and potassium iodide in a solvent to perform a substitution reaction to obtain compound 2;

[0014] 2) hydrolyzing compound 2 under alkaline conditions to obtain compound 3;

[0015] 3) dissolving compound 3 in a solvent, and then adding bromoalcohols with different chain lengths, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4-dimethylaminopyridine to perform a condensation reaction to obtain compounds 4a-4j;

[0016] 4) dissolving compounds 4a-4j in a solvent, and performing a nucleophilic substitution reaction with triphenylphosphine to obtain

[0017] Tralopyril-triphenylphosphine derivatives 5a-5j;

[0018] The synthesis process of the Tralopyril-triphenylphosphine derivative is as follows:

[0019]

[0020] Further, in step 1), the molar ratio of bromopyrrole nitrile, ethyl bromoacetate, potassium carbonate and potassium iodide is 1:1-2:1-2:1, and the use amount ratio of the bromopyrrole nitrile and the solvent is 80-100 mmol:500 mL.

[0021] Further, the temperature of the substitution reaction is 75-80°C, and the time of the substitution reaction is 8-10 h.

[0022] Further, in the step 2), the hydrolysis is carried out in the presence of an alkaline reagent and a solvent, and the compound 2, the alkaline reagent and the solvent are used in a ratio of 20 mmol: 10-30 mmol: 150 mL; the temperature of the hydrolysis is 20-30℃, and the hydrolysis time is 4-6 h.

[0023] Further, in the step 3), the molar ratio of the compound 3, the bromoalcohol with different chain lengths, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4-dimethylaminopyridine is 40: 10-20: 10-20: 2-5, and the compound 3 and the solvent are used in a ratio of 40 mmol: 300-500 mL.

[0024] Further, the temperature of the condensation reaction is 0-15℃, and the condensation reaction time is 6-10 h.

[0025] Further, in the step 4), the compound 4a-4j, triphenylphosphine and the solvent are used in a ratio of 5-10 mmol: 5-10 mmol: 250 mL;

[0026] The temperature of the reaction is 75-80℃, and the reaction time is 60-80 h.

[0027] The application further provides a use of a Tralopyril-triphenylphosphine derivative in preparation of a medicine for preventing and treating plant nematode diseases and fungal diseases, the nematodes are Caenorhabditis elegans, Meloidogyne hapla Chitwood, Heterodera glycines; and the fungal diseases include rice sheath blight, sclerotinia rot of rapeseed, wheat take-all disease and rice blast.

[0028] The application has the following beneficial effects:

[0029] The series of compounds synthesized by the application are novel in structure and take Tralopyril as a mother structure; the biological test results show that part of the compounds have better nematocidal and fungicidal activities, and have higher commercial prospects. BRIEF DESCRIPTION OF DRAWINGS

[0030] Figure 1 is a hydrogen spectrum of compound 2-(3-bromo-5-(4-chlorophenyl)-4-cyano-2-(trifluoromethyl)-1H-pyrrol-1-yl)ethyl acetate 3-bromopropyl ester (4a);

[0031] Figure 2 is a high-resolution mass spectrum of compound 2-(3-bromo-5-(4-chlorophenyl)-4-cyano-2-(trifluoromethyl)-1H-pyrrol-1-yl)ethyl acetate 3-bromopropyl ester (4a);

[0032] Figure 3The 1H NMR spectrum of compound 2-(3-bromo-5-(4-chlorophenyl)-4-cyano-2- (trifluoromethyl)-1H-pyrrol-1-yl)ethyl 3-(triphenylphosphoniumyl)propylate (5a) is shown in Figure 1.

[0033] Figure 4 The high resolution mass spectrum of compound 2-(3-bromo-5-(4-chlorophenyl)-4-cyano-2- (trifluoromethyl)-1H-pyrrol-1-yl)ethyl 3-(triphenylphosphoniumyl)propylate (5a) is shown in Figure 2. DETAILED DESCRIPTION

[0034] The present application provides a Tralopyril-triphenylphosphine derivative, which has the following structural formula:

[0035]

[0036] wherein n = 3-12.

[0037] In the present application, the Tralopyril-triphenylphosphine derivative is a derivative of 4-bromo-2-(4-chlorophenyl)-5-trifluoromethyl-1H-pyrrole-3-carbonitrile.

[0038] In the present application, the Tralopyril-triphenylphosphine derivative is preferably a compound having the following structural formula:

[0039]

[0040]

[0041] In the present application, the molecular structure and physicochemical properties of the above compound are shown in Table 1.

[0042] Table 1 Molecular structure and physicochemical properties of Tralopyril-triphenylphosphine derivative and intermediate 4a

[0043]

[0044] Table 2 1H NMR and high resolution mass spectrum (HRMS) data of Tralopyril-triphenylphosphine derivative and intermediate 4a

[0045]

[0046]

[0047]

[0048] The present application also provides a preparation method of Tralopyril-triphenylphosphine derivative, comprising the following steps:

[0049] 1) Substitution reaction is carried out by mixing bromopyrrole nitrile, ethyl bromoacetate, potassium carbonate and potassium iodide in a solvent to obtain compound 2;

[0050] 2) Compound 2 is hydrolyzed under alkaline conditions to obtain compound 3;

[0051] 3) Compound 3 is dissolved in a solvent, and then condensation reaction is carried out by adding bromoalcohols with different chain lengths, 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride and 4-dimethylaminopyridine to obtain compounds 4a-4j;

[0052] 4) Nucleophilic substitution reaction is carried out by dissolving compounds 4a-4j in a solvent and with triphenylphosphine to obtain

[0053] Tralopyril-triphenylphosphine derivatives 5a-5j;

[0054] The synthesis process of the Tralopyril-triphenylphosphine derivative is as follows:

[0055]

[0056] In the present application, in step 1), the molar ratio of bromopyrrole nitrile, ethyl bromoacetate, potassium carbonate and potassium iodide is 1:1-2:1-2:1, and preferably 1:1.5:1.5:1; the use amount ratio of bromopyrrole nitrile and the solvent is 80-100 mmol:500 mL, and preferably 100 mmol:500 mL.

[0057] In the present application, the temperature of the substitution reaction is 75-80°C, and preferably 76-79°C; the time of the substitution reaction is 8-10 h, and preferably 9 h.

[0058] In the present application, in step 2), the hydrolysis is carried out in the presence of an alkaline reagent and a solvent, and the use amount ratio of compound 2, the alkaline reagent and the solvent is 20 mmol:10-30 mmol:150 mL, and preferably 20 mmol:20 mmol:150 mL; the temperature of the hydrolysis is 20-30°C, and preferably 25°C; the time of the hydrolysis is 4-6 h, and preferably 5 h.

[0059] In the present application, in step 3), the molar ratio of compound 3, bromoalcohols with different chain lengths, 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride and 4-dimethylaminopyridine is 40:10-20:10-20:2-5, and preferably 40:15:15:3;

[0060] The ratio of the compound 3 and the solvent is 40mmol:300-500mL, preferably 40mmol:400mL.

[0061] In the present application, the temperature of the condensation reaction is 0-15℃, preferably 5-10℃; the time of the condensation reaction is 6-10h, preferably 8-10h.

[0062] In the present application, in the step 4), the ratio of the compound 4a-4j, triphenylphosphine and the solvent is 5-10mmol:5-10mmol:250mL, preferably 6-8mmol:6-8mmol:250mL; the temperature of the reaction is 75-80℃, preferably 76-78℃; the time of the reaction is 60-80h, preferably 72h.

[0063] The present application also provides a use of the Tralopyril-triphenylphosphine derivative in the preparation of a medicine for preventing and treating plant nematode diseases and fungal diseases, wherein the nematode is Caenorhabditis elegans, Meloidogyne incognita or Heterodera glycines; and the plant disease comprises rice sheath blight, sclerotinia of rape, wheat take-all and rice blast.

[0064] The technical solutions provided by the present application are described in detail below in combination with examples, but they should not be understood as limitations to the protection scope of the present application.

[0065] Example 1

[0066] Synthesis of compound 5a:

[0067] (1) Synthesis of ethyl 2-(3-bromo-5-(4-chlorophenyl)-4-cyano-2-(trifluoromethyl)-1H-pyrrol-1-yl)acetate

[0068] Dissolve bromopyrrole nitrile (100mmol), potassium carbonate (150mmol) and potassium iodide (100mmol) in 500mL acetonitrile, stir uniformly, then slowly drop ethyl bromoacetate (150mmol), heat to 80℃ to reflux for 9h, after the reaction is completed, spin dry the solvent, extract with dichloromethane and saturated brine, combine the organic phase and dry with anhydrous sodium sulfate. Concentrate under reduced pressure, separate by silica gel column chromatography (V(petroleum ether):V(ethyl acetate)=12:1), to obtain white powdery solid, with a yield of 95%.

[0069]

[0070] (2) Synthesis of 2-(3-bromo-5-(4-chlorophenyl)-4-cyano-2-(trifluoromethyl)-1H-pyrrol-1-yl)acetic acid

[0071] Ethyl 2-(3-bromo-5-(4-chlorophenyl)-4-cyano-2-(trifluoromethyl)-1H-pyrrol-1- yl)acetate (20 mmol), lithium hydroxide (30 mmol) were dissolved in 150 mL of MeOH, stirred at 25 °C for 4-6 h, thin layer chromatography (TLC, V(petroleum ether):V(ethyl acetate) = 6:1) to monitor the reaction was completed. The reaction solution was rotary evaporated to dryness, and then dissolved in water. The pH was adjusted to weakly acidic (5.5) by 2 mmol of HCl. A large amount of white solid was precipitated, which was filtered and dried to obtain a white powder with a yield of 95%.

[0072]

[0073] (3) Synthesis of 3-bromopropyl 2-(3-bromo-5-(4-chlorophenyl)-4-cyano-2- (trifluoromethyl)-1H-pyrrol-1-yl)acetate (compound 4a)

[0074] Ethyl 2-(3-bromo-5-(4-chlorophenyl)-4-cyano-2-(trifluoromethyl)-1H-pyrrol-1- yl)acetate (20 mmol), lithium hydroxide (30 mmol) were dissolved in 150 mL of MeOH, stirred at 25 °C for 4-6 h, thin layer chromatography (TLC, V(petroleum ether):V(ethyl acetate) = 6:1) to monitor the reaction was completed. The reaction solution was rotary evaporated to dryness, and then dissolved in water. The pH was adjusted to weakly acidic (5.5) by 2 mmol of HCl. A large amount of white solid was precipitated, which was filtered and dried to obtain a white powder with a yield of 95%.

[0075]

[0076] (4) Synthesis of 3-(triphenylphosphoranylidene)propyl 2-(3-bromo-5-(4- chlorophenyl)-4-cyano-2-(trifluoromethyl)-1H-pyrrol-1-yl)acetate

[0077] Ethyl 2-(3-bromo-5-(4-chlorophenyl)-4-cyano-2-(trifluoromethyl)-1H-pyrrol-1- yl)acetate (20 mmol), lithium hydroxide (30 mmol) were dissolved in 150 mL of MeOH, stirred at 25 °C for 4-6 h, thin layer chromatography (TLC, V(petroleum ether):V(ethyl acetate) = 6:1) to monitor the reaction was completed. The reaction solution was rotary evaporated to dryness, and then dissolved in water. The pH was adjusted to weakly acidic (5.5) by 2 mmol of HCl. A large amount of white solid was precipitated, which was filtered and dried to obtain a white powder with a yield of 95%.

[0078]

[0079] The synthesis of Tralopyril-triphenylphosphine derivatives 5a-5j in this series of the present application all adopt this route, and the synthesis methods are similar, and thus will not be described again.

[0080] The relationship table of Tralopyril-triphenylphosphine derivatives 5a-5j and corresponding raw materials is as follows:

[0081] Table 3

[0082]

[0083]

[0084] For the compounds in the present application, we carried out nematode activity test. The nematode activity determination of the target compounds adopts direct contact killing method. Caenorhabditis elegans is selected as the test nematode, bromopyrrole nitrile (Tralopyril) and thiazophos (Fosthiazate) are selected as the control agents, the initial screening concentration of the agents is set to 100 mg / L, the test compound is dissolved in 1 mL DMF, and then diluted to 25 mL with 0.1% Tween 80 aqueous solution. The cultured nematodes are eluted with sterile water, the eluate is concentrated by centrifugation, and then a certain proportion of nematode suspension (80-120 per 100 μL) is prepared. 100 μL of the nematode suspension is taken into a 96-well biochemical culture plate with a pipette, and then 80 μL of sterile water and 20 μL of the test drug solution are added. After the addition is completed, the biochemical culture plate is placed in a 20°C constant temperature incubator, and the total number and the number of dead nematodes of each treatment are observed under a stereoscope 48 h after the treatment, and each treatment is repeated three times. The death standard of nematodes is that the nematodes are rigid, and do not move when stimulated with a fine needle, and thus the nematodes are considered to have died. The nematode killing activity of the test compound is calculated. According to the initial screening results, the compounds with nematode killing activity greater than 75% are selected for further determination of the LC 50 values of Caenorhabditis elegans, and the data processing software DPS18.10 is used to calculate the LC 50Values and 95% confidence intervals. Some of the high activity compounds screened by C. elegans were further determined for their bioactivity against root-knot nematode by pot experiment. The 4-5 leaf stage tomato seedlings were transplanted into a 20 cm diameter plastic pot, one plant per pot. The soil used for cultivating tomato seedlings in the pot was a mixture of loam and substrate soil 1:1, 2 kg per pot. After the tomato seedlings were planted, fresh tomato root systems with root-knots were selected, the root-knots were cut and crushed into small pieces of about 5 mm x 5 mm, 10 g of root-knot small pieces were added to each pot, each test compound was dissolved in 1 mL of dimethyl sulfoxide (DMSO), then diluted with 0.1% Tween 80 to 100 mL to prepare a certain concentration of drug solution. Each treatment group had 6 replicates, and 72 hours after inoculation of southern root-knot nematodes, the test solution was poured around the roots of the tomato seedlings using a beaker, 0.1% Tween 80 containing the same volume of DMSO was used as a blank control, bromopyrrole nitrile (Tralopyril) and trifluoropyridylamine (Cyclobutrifluram) were used as positive controls. After application, the tomato seedlings were cultured in a greenhouse, and after 35 days of normal growth, the root disease of the tomato seedlings was investigated and rated, and the disease index was calculated. The control effect (%) was calculated according to the following formula:

[0085]

[0086] Table 4 in vitro nematicidal activity of target compounds against C. elegans

[0087]

[0088]

[0089] Table 5 LC of some target compounds against C. elegans 50

[0090]

[0091] From the results in Table 5, at a concentration of 100 mg / L, the target compounds generally showed high bioactivity against C. elegans, all better than the control agent thiazolylphosphine. 50 The LC values in Table 6 show that compounds 5b, 5f, and 5h have higher toxicity than the control agent thiazolylphosphine.

[0092] Table 6 control effect of some target compounds against southern root-knot nematode

[0093]

[0094] From the results in Table 6, using the root irrigation method, the control effect of compound 5f is higher than that of the control agent trifluoropyridylamine, and lower than that of the parent compound bromopyrrole nitrile.

[0095] For the compounds in the present application, we carried out bactericidal activity test. The mycelial growth rate method was used to determine the bactericidal activity of the compounds on various fungi in a culture dish. The cultured pathogenic fungi were cut into a 7mm diameter cake from the edge of the colony under sterile conditions, and the cake was inoculated with an inoculation needle in the center of the culture medium dish, with the mycelium facing down. The dish was covered with a lid, inverted, and placed in a 25°C incubator for culture. When the colonies in the blank control grew to about two-thirds of the area of the dish, the diameters of the colonies in each treatment were measured by the cross method, with 3 replicates for each sample and the average value was taken. The mycelial growth inhibition rate of each fungicide treatment on the pathogenic fungi was calculated by the ratio of the difference between the colony diameters of the blank control and the fungicide treatment to the colony diameter of the blank control. The results of the preliminary screening of the compounds of the present application on Rhizoctonia solani, Sclerotinia sclerotiorum, Septoria nodorum, and Pyricularia oryzae are shown in Table 7, and the EC 50 values of some compounds with an activity higher than 85% on Rhizoctonia solani and Sclerotinia sclerotiorum are shown in Table 8.

[0096] The results in Table 7 show that the target compounds exhibit high biological activity on the four pathogenic fungi. At a concentration of 50mg / L, the toxicity of compound 5a on Rhizoctonia solani is higher than that of the control agent azoxystrobin, and the toxicity of compounds 5d and 5f on Sclerotinia sclerotiorum is higher than that of the control agent azoxystrobin. The toxicity of all compounds on Pyricularia oryzae is higher than that of fludioxonil.

[0097] Table 7 Results of the bactericidal activity test of the compounds on four pathogenic fungi in a culture dish (50mg / L)

[0098]

[0099] EC 50 values of some target compounds on the test plant pathogenic fungi are shown in Table 8, in which the activity of compounds 5b, 5c, 5d, and 5f on Sclerotinia sclerotiorum is higher than that of the commercial agent azoxystrobin.

[0100] Table 8 EC 50

[0101]

[0102] From the above examples, the application provides a Tralopyril-triphenylphosphine derivative, a preparation method and application thereof. The application uses Tralopyril as a parent structure, couples and splices a flexible chain with different lengths and a triphenylphosphine cation to synthesize a series of new compounds, and the chemical structure is novel. The biological test results show that in terms of nematode killing, the toxicity of some compounds to Caenorhabditis elegans is higher than that of the commercial agent fosted. In the root-knot nematode potting activity test, the compound 5f has a higher root irrigation activity than the control agent triforine. In terms of bactericidal activity, the compounds have higher biological activity on Rhizoctonia solani, Sclerotinia sclerotiorum, Gaeumannomyces graminis and Magnaporthe oryzae, and the activity of the compounds 5b, 5c, 5d and 5f on Sclerotinia sclerotiorum is higher than that of the commercial agent azoxystrobin. The synthesized new compounds have a high commercial prospect.

[0103] The above only describes the preferred embodiments of the application, and it should be noted that for those skilled in the art, some improvements and refinements can be made without departing from the principles of the application, and these improvements and refinements should also be considered as the protection scope of the application.

Claims

1. A Tralopyril-triphenylphosphine derivative, characterized in that, The Tralopyril-triphenylphosphine derivative has the following structural formula: Where n = 3 to 12.

2. The Tralopyril-triphenylphosphine derivative according to claim 1, characterized in that, The Tralopyril-triphenylphosphine derivative is selected from compounds with the following structural formulas:

3. The method for preparing the Tralopyril-triphenylphosphine derivative according to claim 1 or 2, characterized in that, Includes the following steps: 1) A substitution reaction was carried out by mixing bromopyrrolidone, ethyl bromoacetate, potassium carbonate and potassium iodide in a solvent to obtain compound 2; 2) Compound 2 was hydrolyzed under alkaline conditions to give compound 3; the hydrolysis was carried out in the presence of the alkaline reagent LiOH and the solvent. 3) Compound 3 was dissolved in a solvent, and then bromools of different chain lengths, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4-dimethylaminopyridine were added to carry out a condensation reaction to obtain compounds 4a to 4j. 4) Compounds 4a-4j were dissolved in a solvent and subjected to a nucleophilic substitution reaction with triphenylphosphine to obtain Tralopyril-triphenylphosphine derivatives 5a-5j; The synthesis process of the Tralopyril-triphenylphosphine derivative is as follows:

4. The method for preparing the Tralopyril-triphenylphosphine derivative according to claim 3, characterized in that, In step 1), the molar ratio of bromopyrrolidone, ethyl bromoacetate, potassium carbonate, and potassium iodide is 1:1 to 2:1 to 2:1, and the ratio of bromopyrrolidone to solvent is 80 to 100 mmol: 500 mL.

5. The method for preparing the Tralopyril-triphenylphosphine derivative according to claim 4, characterized in that, The substitution reaction is carried out at a temperature of 75–80°C for 8–10 hours.

6. The method for preparing the Tralopyril-triphenylphosphine derivative according to claim 5, characterized in that, In step 2), the ratio of compound 2, alkaline reagent and solvent is 20 mmol: 10-30 mmol: 150 mL; the hydrolysis temperature is 20-30 °C and the hydrolysis time is 4-6 h.

7. The method for preparing the Tralopyril-triphenylphosphine derivative according to claim 3 or 6, characterized in that, In step 3), the molar ratio of compound 3, bromools of different chain lengths, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4-dimethylaminopyridine is 40:10-20:10-20:2-5, and the ratio of compound 3 to solvent is 40 mmol:300-500 mL.

8. The method for preparing the Tralopyril-triphenylphosphine derivative according to claim 7, characterized in that, The condensation reaction is carried out at a temperature of 0–15°C for 6–10 hours.

9. The method for preparing the Tralopyril-triphenylphosphine derivative according to any one of claims 3, 6, or 8, characterized in that, In step 4), the ratio of compounds 4a-4j, triphenylphosphine, and solvent is 5-10 mmol: 5-10 mmol: 250 mL. The reaction temperature is 75–80°C, and the reaction time is 60–80 h.

10. The use of the Tralopyril-triphenylphosphine derivative according to claim 1 or 2 in the preparation of a drug for controlling plant nematode diseases and fungal diseases, characterized in that, The nematodes are *Cryptospira elegans* and *Root-knot nematode*; the fungal diseases are rice sheath blight, rapeseed sclerotinia stem rot, wheat take-all disease, and rice blast.

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