Application of an isobenzofuran compound in controlling plant root-knot nematodes

Abstract

The present invention discloses the application of an isobenzofuran compound in the control of plant root-knot nematodes. The isobenzofuran compound is 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1. The present invention provides a new candidate compound 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 for the control of plant root-knot nematodes, which has strong toxic effects on various plant root-knot nematodes and has no insecticidal activity against the model nematode of non-plant pathogenic nematodes, and has the characteristics of high efficiency and low toxicity. The present invention enriches the structural types of isobenzofuran compounds for killing root-knot nematodes and provides new ideas and ways for the development of new pesticides for killing root-knot nematodes.

Description

Technical Field

[0001] The invention belongs to the technical field of agricultural pest control, and specifically relates to application of isobenzofuran compounds in the control of plant root-knot nematodes. Background Art

[0002] Global ecosystems and agricultural production are suffering from serious threats from plant parasitic nematodes, especially root-knot nematodes. Root-knot nematodes are recognized as one of the most destructive plant diseases in the world. They invade the root system of plants, seriously hindering the normal absorption of nutrients and water by plants, causing slow growth of crops, and even causing the complete death of crops, with a sharp decline in both yield and quality. However, the hidden nature and complexity of root-knot nematode diseases make their prevention and control extremely difficult, and have become a problem that needs to be solved urgently worldwide. It is particularly noteworthy that environmental differences in different regions lead to great differences in the sensitivity of root-knot nematodes to chemical substances, which undoubtedly increases the difficulty of prevention and control. Traditional chemical nematicides have gradually been eliminated due to their high toxicity, potential carcinogenic risks and serious pollution to the environment. In view of this, the current research focus has shifted to the development of new, efficient and low-toxic nematicidal compounds, and on this basis, to create more environmentally friendly and safe pesticide products to cope with the severe challenges brought by root-knot nematodes.

[0003] The present invention aims to provide an application of isobenzofuran compounds in controlling plant root-knot nematodes. Summary of the invention

[0004] The object of the present invention is to provide an application of isobenzofuran compounds in controlling plant root-knot nematodes.

[0005] The object of the present invention is achieved by using an isobenzofuran compound 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 and / or its pesticide acceptable salt in controlling plant root knot nematodes. The structural formula of the isobenzofuran compound 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 is as shown in Formula I:

[0006]

[0007] I.

[0008] The present invention provides a new candidate compound 3 - ((4 - (3 - bromophenyl)thiazol - 2 - yl)amino)isobenzofuran - 1(3H)-one for the control of plant root - knot nematodes. It has a strong toxic effect on various plant root - knot nematodes, has no insecticidal activity against the model nematode of non - plant pathogenic nematodes, and has the characteristics of high efficiency and low toxicity. The present invention enriches the structural types of isobenzofuran compounds for killing root - knot nematodes and provides new ideas and approaches for the development of new pesticides for killing root - knot nematodes. BRIEF DESCRIPTION OF THE DRAWINGS

[0009] Figure 1 is the structural formula of the compound 3 - ((4 - (3 - bromophenyl)thiazol - 2 - yl)amino)isobenzofuran - 1(3H)-one of the present invention;

[0010] Figure 2 is the calculation result of the toxicity determination of the compound 3 - ((4 - (3 - bromophenyl)thiazol - 2 - yl)amino)isobenzofuran - 1(3H)-one in Example 1 against Meloidogyne incognita;

[0011] Figure 3 is the calculation result of the toxicity determination of 3 - ((4 - (3 - bromophenyl)thiazol - 2 - yl)amino)isobenzofuran - 1(3H)-one in Example 1 against Meloidogyne javanica;

[0012] Figure 4 is the calculation result of the toxicity determination of 3 - ((4 - (3 - bromophenyl)thiazol - 2 - yl)amino)isobenzofuran - 1(3H)-one in Example 1 against Meloidogyne enterolobii;

[0013] Figure 5 is the nuclear magnetic resonance hydrogen spectrum of the compound 3 - ((4 - (3 - bromophenyl)thiazol - 2 - yl)amino)isobenzofuran - 1(3H)-one of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0014] The following examples are used to further illustrate the present invention in detail, but the present invention is not limited in any way. Any transformation or improvement based on the teachings of the present invention falls within the protection scope of the present invention.

[0015] The present invention provides the application of 3 - ((4 - (3 - bromophenyl)thiazol - 2 - yl)amino)isobenzofuran - 1(3H)-one and / or its agriculturally acceptable salts in the control of plant root - knot nematodes. The structural formula of the compound 3 - ((4 - (3 - bromophenyl)thiazol - 2 - yl)amino)isobenzofuran - 1(3H)-one is as Figure 1As shown. This compound is a new compound, sourced from the drug-like diversity compound library 50K Diversity Library containing 50,000 compounds developed by MCE (MedChemExpress). Its Catalog Number is HY-L901 and Library ID is HY-LD-000004591. The Catalog Number of the said compound is HY-Q08575, without a CAS Number yet. The relative molecular mass is 387.25, and the mass-to-charge ratio m / z is 385.97 (100.0%), 387.97 (97.3%), 388.97 (17.9%).

[0016]

[0017] I.

[0018] The root-knot nematodes are Meloidogyne incognita, Meloidogyne javanica or Meloidogyne enterolobii.

[0019] The present invention also provides an insecticide for controlling plant root-knot nematodes, where the insecticide uses 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 and / or its agrochemically acceptable salts as one of the main active ingredients or active ingredients.

[0020] The concentration of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 in the said insecticide is ≥5 μg / ml.

[0021] The dosage form of the said insecticide is aqueous solution, emulsion in water, wettable powder, soluble powder, soluble granule, suspension concentrate, tablet or effervescent granule.

[0022] The solvent of the said aqueous solution or emulsion in water is an aqueous solution of fatty alcohol with a concentration ≤5%.

[0023] The said fatty alcohol is methanol, ethanol or propanol.

[0024] Example 1 Detection of the nematicidal activity of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1

[0025] 1. Sample preparation

[0026] Dissolve 0.5 - 1.5 mg of 3 - ((4 - (3 - bromophenyl)thiazol - 2 - yl)amino)isoindole - 1(3H)-one in DMSO, and dilute it with a 4% DMSO solution to obtain the test liquid medicine. The dilution concentrations of each liquid medicine are: 0.03 μg / ml, 0.05 μg / ml, 0.1 μg / ml, 0.3 μg / ml, 0.5 μg / ml, 1 μg / ml, 3 μg / ml, 5 μg / ml, 10 μg / ml, 30 μg / ml, 50 μg / ml, and the mass concentration of DMSO in each liquid medicine is 0.4%; use water containing 0.4% DMSO as the blank control.

[0027] 2. Preparation of test nematodes

[0028] Wash the tomato roots infected with Meloidogyne incognita with water, pick the egg sacs of root - knot nematodes with a dissecting needle and place them in a 0.4 M KCl solution. In a 5 - ml centrifuge tube, wash and disinfect them successively with 4 ml of sterile water (three times), 1 ml of sterile penicillin - streptomycin double - antibody solution, and 3 ml of 0.1% NaClO solution. In each step, remove the supernatant by brief centrifugation (8000 rpm for 30 seconds). Place the washed eggs in a 0.4 M ZnCl2 solution and incubate for 48 hours. Collect the second - stage larvae with a pipette into a 1.5 - ml centrifuge tube and enrich them by brief centrifugation (5000 rpm for 30 seconds) for standby.

[0029] In addition, in this experiment, test nematodes such as Meloidogyne javanica, Meloidogyne enterolobii, and Caenorhabditis elegans were also prepared according to conventional methods.

[0030] 3. Test method

[0031] Take 100 μl of each test liquid medicine prepared in step 1 into a 20 - well plate, add 50 - 100 live nematodes prepared in step 2, place them at 25°C, and check and calculate the mortality rate of nematodes under an optical microscope at 24 hours, 48 hours, and 72 hours respectively. The method for identifying death is: add 1 - 5 drops of 5% NaCl solution to the wells of the treatment plate, observe after 2 minutes. Dead worms are rigid and have no reaction when stimulated with a needle, while live worms curl or wriggle.

[0032] Use the test solution without adding samples as the control. Repeat the whole experiment three times, take the average of the three times, and calculate the corrected mortality rate.

[0033] Mortality rate % = (Number of dead nematodes / (Number of dead nematodes + Number of surviving nematodes)) × 100%

[0034] Corrected mortality rate % = Sample mortality rate - Control mortality rate

[0035] 4. Experimental results

[0036] 4.1 The toxicity of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-one against Meloidogyne incognita is shown in Table 1 and Figure 2 as follows:

[0037] Table 1 Toxicity results of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-one against Meloidogyne incognita

[0038]

[0039] 4.2 The toxicity of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-one against Meloidogyne javanica is shown in Table 2 and Figure 3 as follows:

[0040] Table 2 Toxicity results of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-one against Meloidogyne javanica

[0041]

[0042] 4.3 The toxicity of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-one against Meloidogyne enterolobii is shown in Table 3 and Figure 4 as follows:

[0043] Table 3 Toxicity results of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-one against Meloidogyne enterolobii

[0044]

[0045] 4.4 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-one has no toxicity against the non-plant pathogenic nematode Caenorhabditis elegans within 24 hours.

[0046] Result analysis: After determination ( Figures 2 - 4 ), the median lethal concentration LC 50 of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-one against Meloidogyne incognita, Meloidogyne javanica and Meloidogyne enterolobii within 24 hours are 11.54 μg / ml, 15.53 μg / ml, 16.96 μg / ml respectively; the median lethal concentration LC 50With concentrations of 10.71 μg / ml, 15.22 μg / ml, and 17.02 μg / ml respectively, it has a strong insecticidal effect on Meloidogyne incognita, Meloidogyne javanica, and Meloidogyne enterolobii, but has no insecticidal activity against the non-plant pathogenic nematode Caenorhabditis elegans, and can be used for the control of plant root-knot nematodes.

[0047] Example 2

[0048] An insecticide for controlling plant root-knot nematodes, wherein the insecticide uses a 3% methanol solution as a solvent and 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 with a concentration of 30 μg / ml as an active ingredient.

[0049] Example 3

[0050] An insecticide for controlling plant root-knot nematodes, wherein the insecticide uses a 4% ethanol solution as a solvent and 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 with a concentration of 50 μg / ml as an active ingredient.

[0051] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited by the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications made without departing from the spirit and principle of the present invention shall be equivalent replacement methods and are all included in the protection scope of the present invention.

Claims

1. The use of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 in the control of plant root-knot nematodes, characterized in that: The structural formula of the 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 is as shown in Formula I: I； The root-knot nematode is the southern root-knot nematode, the javanic root-knot nematode or the elephant-ear bean root-knot nematode, and the application concentration of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 is ≥5 μg / mL.

2. A pesticide for controlling plant root-knot nematodes, characterized in that: The insecticide uses 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 in claim 1 as an active ingredient.

3. The insecticide according to claim 2, characterized in that: The concentration of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 in the insecticide is ≥5 μg / mL.

4. The insecticide according to claim 2, characterized in that: The dosage form of the insecticide is water-based, water-emulsified, wettable powder, soluble powder, soluble granule, suspension, tablet or effervescent granule.

5. The insecticide according to claim 4, characterized in that: The solvent of the aqueous solution or aqueous emulsion is a fatty alcohol aqueous solution with a concentration of ≤5%.

6. The insecticide according to claim 5, characterized in that: The fatty alcohol is methanol, ethanol or propanol.

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