Application of isobenzofuran compound in prevention and control of plant root-knot nematode

Abstract

The invention discloses an application of an isobenzofuran compound in prevention and control of plant root-knot nematode. And the isobenzofuran compound is 3-((4-(3-bromophenyl) thiazole-2-yl) amino) isobenzofuran-1 (3H)-1. The invention provides a novel candidate compound 3-((4-(3-bromophenyl) thiazole-2-yl) amino) isobenzofuran-1 (3H)-1 for a medicine for preventing and treating plant root-knot nematodes, and the compound has a relatively strong poisoning effect on various plant root-knot nematodes, has no insecticidal activity on mode nematodes of non-plant pathogenic nematodes, and has the characteristics of high efficiency and low toxicity. The structural types of the isobenzofuran compound for killing the root-knot nematode are enriched, and a new thought and a new approach are provided for development of a new pesticide for killing the root-knot nematode.

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: I.

[0006] 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 a strong toxic effect on various plant root-knot nematodes, has no insecticidal activity on model nematodes 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 that kill root-knot nematodes, and provides new ideas and approaches for the development of new pesticides that kill root-knot nematodes. BRIEF DESCRIPTION OF THE DRAWINGS

[0007] Figure 1 is the structural formula of the compound 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 of the present invention; Figure 2 The calculation result of the toxicity determination of the compound 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 in Example 1 against southern root knot worm; Figure 3 The calculation result of the toxicity determination of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 against javanica root-knot nematode in Example 1; Figure 4 The calculation result of the toxicity determination of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 against the ear bean root knot nematode in Example 1; Figure 5 The figure is the hydrogen nuclear magnetic resonance spectrum of the compound 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 of the present invention. DETAILED DESCRIPTION

[0008] The present invention is further described in detail below in conjunction with the embodiments, but the present invention is not limited in any way. Any changes or improvements made based on the teachings of the present invention fall within the protection scope of the present invention.

[0009] The present invention provides the use of 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 compound 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 is as follows: Figure 1 As shown. This compound is a new compound, which comes from the 50KDiversity Library, a drug-like diversity compound 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 compound is HY-Q08575, and there is no CAS Number. The relative molecular mass is 387.25, and the mass-to-charge ratio m / z is 385.97 (100.0%), 387.97 (97.3%), and 388.97 (17.9%).

[0010] I.

[0011] The root-knot nematode is the southern root-knot nematode, the javanic root-knot nematode or the elephant-ear bean root-knot nematode.

[0012] The present invention also provides an insecticide for controlling plant root-knot nematodes, wherein the insecticide uses the compound 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 and / or its pesticide-acceptable salt as a main active ingredient or one of the active ingredients.

[0013] The concentration of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 in the insecticide is ≥5 μg / ml.

[0014] The dosage form of the insecticide is water-based, water-emulsified, wettable powder, soluble powder, soluble granule, suspension, tablet or effervescent granule.

[0015] The solvent of the aqueous solution or aqueous emulsion is a fatty alcohol aqueous solution with a concentration of ≤5%.

[0016] The fatty alcohol is methanol, ethanol or propanol.

[0017] Example 1 Detection of Nematicidal Activity of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 1. Sample preparation Dissolve 0.5~1.5mg of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 in DMSO and dilute it with 4% DMSO solution as the test solution. The dilution concentrations of each solution 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, 50μg / ml, and the mass concentration of DMSO in each solution is 0.4%; water containing 0.4% DMSO is used as a blank control.

[0018] 2. Preparation of Nematodes for Experiment The tomato roots infected with southern root-knot nematodes were washed with water, the root-knot nematode egg capsules were picked up with a dissecting needle and placed in a 0.4 M KCl solution, and then washed and disinfected in a 5 ml centrifuge tube with 4 ml sterile water (three times), 1 ml sterile penicillin-streptomycin double antibody solution, and 3 ml 0.1% NaClO solution. The supernatant was removed by brief centrifugation (8000 rpm for 30 seconds) in each step. The washed eggs were placed in a 0.4 M ZnCl2 solution for incubation for 48 hours, and the second-instar larvae were collected in a 1.5 ml centrifuge tube with a pipette and enriched by brief centrifugation (5000 rpm for 30 seconds) for later use.

[0019] In addition, this experiment also prepared experimental nematodes such as Java root-knot nematode, elephant ear bean root-knot nematode and Caenorhabditis elegans according to conventional methods.

[0020] 3. Test methods Take 100 μl of each test solution prepared in step 1 in a 20-well plate, add 50-100 live nematodes prepared in step 2, place at 25°C, and check and calculate the mortality of nematodes under an optical microscope at 24 hours, 48 ​​hours, and 72 hours. 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, the dead worms are stiff, no response to needle stimulation, and the live worms are curled or twisted.

[0021] The test solution without sample was used as control, the whole experiment was repeated three times, the average of the three times was taken to calculate the corrected mortality rate.

[0022] Mortality % = (number of dead nematodes / (number of dead nematodes + number of surviving nematodes)) × 100% Corrected mortality % = sample mortality – control mortality 4. Experimental results 4.1 The toxicity of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 against southern root-knot nematodes is shown in Table 1 and Figure 2 As shown: Table 1 The results of toxicity of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran to southern root-knot nematode 4.2 The toxicity of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 against javanic root-knot nematodes is shown in Table 2 and Figure 3 shown.

[0023] Table 2 The toxicity of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 to Javan root-knot nematode 4.3 The toxicity of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 against the root-knot nematode of R. sphaeroides is shown in Tables 3 and Figure 4 As shown: Table 3 The toxicity results of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 on root knot nematodes of ear bean 4.4 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 had no toxic activity against the non-plant pathogenic nematode Caenorhabditis elegans within 24 hours.

[0024] Result analysis: After determination ( Figure 2-4 ), 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran has a 24-hour LD50 against southern root-knot nematodes, javanic root-knot nematodes and elephant ear bean root-knot nematodes 50 The concentrations were 11.54 μg / ml, 15.53 μg / ml, and 16.96 μg / ml, respectively; the median lethal dose LC of the southern root-knot nematode, the Javan root-knot nematode, and the elephant-ear bean root-knot nematode was 48 hours. 50 The concentrations were 10.71 μg / ml, 15.22 μg / ml and 17.02 μg / ml respectively. They had strong toxic effects on southern root-knot nematodes, Javan root-knot nematodes and elephant-ear bean root-knot nematodes, but had no toxic activity on non-plant pathogenic nematodes Caenorhabditis elegans. They can be used for the prevention and control of plant root-knot nematodes.

[0025] Example 2 The invention discloses an insecticide for controlling plant root-knot nematodes. 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.

[0026] Example 3 The invention discloses an insecticide for controlling plant root-knot nematodes. 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.

[0027] The above embodiments are preferred implementation modes of the present invention, but the implementation modes of the present invention are not limited to the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications that do not deviate from the spirit and principles of the present invention should be equivalent replacement methods and are included in the protection scope of the present invention.

Claims

1. Use of 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 and / or its pesticide acceptable salts in controlling 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。 2. The application according to claim 1, characterized in that: The root-knot nematode is the southern root-knot nematode, the javanic root-knot nematode or the elephant-ear bean root-knot nematode.

3. A pesticide for controlling plant root-knot nematodes, characterized in that: The insecticide uses the compound 3-((4-(3-bromophenyl)thiazol-2-yl)amino)isobenzofuran-1(3H)-1 and / or its pesticide acceptable salt as the main active ingredient or one of the active ingredients.

4. The insecticide according to claim 3, 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.

5. The insecticide according to claim 3, 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.

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

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

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