An agricultural antibacterial / viral agent containing a benzazole compound and use thereof for controlling plant diseases

Abstract

The application belongs to the technical field of agricultural antibacterial / viral agents, and relates to an agricultural antibacterial / viral agent containing a benzoxazinone compound and a use of the agricultural antibacterial / viral agent in preventing and treating crop diseases, in particular to an agricultural antibacterial / viral agent containing 6-methoxy-2-benzoxazinone or a pesticide-acceptable salt thereof shown in formula I and a use of the agricultural antibacterial / viral agent in preventing and treating crop diseases. The 6-methoxy-2-benzoxazinone can be used to prevent and treat a wide range of crop diseases with high efficiency, and can be used to efficiently prevent and control various important crop diseases, in particular, can be used to prevent and treat cucumber downy mildew, wheat stripe rust, melon powdery mildew, tobacco bacterial wilt and tobacco common mosaic virus disease, and the effective prevention and control concentration is only 1.0 mg / L-10.0 mg / L.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of agricultural antibacterial / viral agents, and relates to an agricultural antibacterial / viral agent containing a benzoxazinone compound and the use thereof in preventing and treating crop diseases; in particular, to an antibacterial / viral agent containing 6-methoxy-2-benzoxazinone or a pesticide-acceptable salt thereof and the use thereof in preventing and treating crop diseases. BACKGROUND

[0002] Since Xiaoyangying and Masatoshi Yamato isolated coixol from the methanol extract of the roots of Coix lachrymal-jobi L. and identified its structure as 6-methoxy-2-benzoxazinone (“Coixol and Betulinic Acid from the Roots of Coix lachryma-jobi L.”, Li Qixun, Li Yunchang, Nie Ruilin, Zhou Jun, Yunnan Research on Plants, 1981, 3(4): 475-477; “Studies on the Constituents of Coix Species. III.: Synthesis of Coixol and its Related Compounds”, Takaji Koyama, Masatoshi Yamato, Kazuhiko Kubota, J. Pharm. Assoc. (Japan), 1956, 76: 1002-1005), there have been many reports of coixol being used in the medical and health care field for analgesia, antipyretic and hypoglycemic purposes (“Coixol and Betulinic Acid from the Roots of Coix lachryma-jobi L.”, Li Qixun, Li Yunchang, Nie Ruilin, Zhou Jun, Yunnan Research on Plants, 1981, 3(4): 475-477). In the field of plant protection, there is only a patent application on the use of 6-methoxy-2-benzoxazinone for attracting and trapping southern root-knot nematodes (Application of 6-methoxy-benzoxazin-2-one in trapping southern root-knot nematodes, application number cn202211364495.7), but there is no report on the use of the compound in agricultural antibacterial / viral agents for preventing and treating crop diseases.

[0003] During the research and development of new agricultural antibacterial / viral agents, the applicant found that 6-methoxy-2-benzoxazinone or a pesticide-acceptable salt thereof has a new use as an inducible disease resistance activator in antibacterial / viral agents, and has excellent prevention and control effects on various crop diseases and is not prone to developing drug resistance. SUMMARY

[0004] The present application provides an agricultural antibacterial / viral agent containing 6-methoxy-2-benzoxazinone or a pesticide-acceptable salt thereof; the antibacterial / viral agent further comprises a pesticide-acceptable carrier. The 6-methoxy-2-benzoxazinone, commonly known as coixol, has a structure as shown in formula I.

[0005]

[0006] The agricultural antibacterial / viral agent of the present application, 6-methoxy-2-benzoxazolinone or its agriculturally acceptable salt, is dissolved or dispersed in a carrier to formulate a preparation, which can be formulated into an emulsifiable concentrate, a suspension concentrate, a flowable concentrate, a microemulsion, an emulsion, a water emulsion, a powder, a wettable powder, a soluble liquid, a soluble powder, a granule, a water dispersible granule, a capsule, or the like; preferably, a dimethyl sulfoxide liquid.

[0007] One or more other antibacterial agents, antiviral agents, insecticides, herbicides, plant growth regulators, and the like can be added to the antibacterial / viral agent of the present application.

[0008] The present application also provides the use of 6-methoxy-2-benzoxazolinone or its agriculturally acceptable salt, or the agricultural antibacterial / viral agent as described above for the prevention and treatment of plant pathogens or viruses.

[0009] The plant pathogens or viruses are Puccinia striiformis west. f. sp. tritici, Pyricularia oryzae, Fusarium pseudograminearum, Xanthomonas oryzae, Pseudoperonspora cubensis, Sphaerotheca fuligimea, Fusarium oxysporum, Phytophthora capsici, Ralstonia solanacearum, and Tobacco Mosaic Virus.

[0010] The present application also provides the use of 6-methoxy-2-benzoxazolinone or its agriculturally acceptable salt, or the agricultural antibacterial / viral agent as described above for the prevention and treatment of plant diseases. The 6-methoxy-2-benzoxazolinone or its agriculturally acceptable salt as an antibacterial / viral agent activates the immune system of the plant itself and enhances its resistance to plant pathogens / viruses.

[0011] The present application also provides a method for preventing and treating plant diseases, which is characterized in that 6-methoxy-2-benzoxazolinone or its agriculturally acceptable salt, or the agricultural antibacterial / viral agent as described above is applied to plants. The active ingredient 6-methoxy-2-benzoxazolinone activates the immune system of the plant itself and enhances its resistance to plant pathogens / viruses, thereby preventing and treating plant diseases.

[0012] The crop diseases can be wheat stripe rust, wheat foot rot, rice blast, rice bacterial leaf streak, cucumber downy mildew, melon powdery mildew, watermelon wilt, pepper late blight, pepper virus disease, tobacco bacterial wilt, tobacco common mosaic virus disease; preferably, the crop diseases are cucumber downy mildew, wheat stripe rust, melon powdery mildew, tobacco bacterial wilt, and tobacco common mosaic virus disease.

[0013] The active ingredient 6-methoxy-2-benzoxazolinone is used at a concentration of 1.0 mg / L to 50.0 mg / L, preferably 1.0 mg / L to 10.0 mg / L.

[0014] The 6-methoxy-2-benzoxazolinone or the pesticide-acceptable salt thereof of the present application, and the agricultural antibacterial / viral agent described above, can be used together with one or more other antibacterial agents, antiviral agents, insecticides, herbicides, plant growth regulators, or fertilizers, etc. The components can be applied simultaneously, sequentially, or separately.

[0015] The pesticide-acceptable salt includes inorganic salts and organic salts. The inorganic salts include at least one of lithium, sodium, potassium, cesium, calcium, magnesium, copper, aluminum, zinc, barium, and quaternary ammonium salts. The organic salts include at least one of acetic acid, benzoic acid, salicylic acid, arginine, lysine, glutamic acid, pyroglutamic acid, and azetidine-2-carboxylic acid salts.

[0016] Compared with the prior art, the present application has the following characteristics and advantages:

[0017] 1. The 6-methoxy-2-benzoxazolinone can be used to prevent and control a wide range of crop diseases with high efficiency, and can be used to effectively prevent and control important crop diseases, in particular, cucumber downy mildew, wheat stripe rust, melon powdery mildew, tobacco bacterial wilt, and tobacco common mosaic virus disease. The effective prevention and control concentration is only 1.0 mg / L to 10.0 mg / L.

[0018] 2. The compound of the present application belongs to a plant-induced disease activator. The compound does not directly kill or inhibit plant pathogens, but stimulates the immune system of the plant itself by regulating multiple signal molecules and endogenous hormones in the plant body, thereby enhancing the resistance of the plant to pathogens. Therefore, the pathogens of the crops are difficult to develop drug resistance. DETAILED DESCRIPTION

[0019] The specific embodiments of the present application are described in detail below. It should be understood that the specific embodiments described herein are only used to illustrate and explain the present application, and are not used to limit the present application.

[0020] The endpoints of the ranges and any values disclosed herein are not limited to the precise values stated. The endpoints of the ranges are provided as a separate embodiment and include any value between the upper and lower bounds. Any numerical value, however, can only be approximate. The numerical characteristics of the application can vary depending on the specific conditions or requirements. The numerical characteristics of the application can be approximated through use of a reasonable number of significant figures. These numerical characteristics should be interpreted, along with the other disclosures in this application, in a non-limiting manner.

[0021] Before describing the present application in detail, it is to be understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present application which is defined solely by the claims. In order to more fully understand the present application described herein, the following terms are defined as follows. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.

[0022] Unless otherwise defined, the following terms used in the present application have the following definitions.

[0023] The term "pesticidally acceptable salt" is a salt of the 6-methoxy-2-benzoxazolinone of the present application, which is prepared by reacting the 6-methoxy-2-benzoxazolinone of the present application with a chemically acceptable acid, which can be an inorganic acid (e.g., hydrochloric acid, sulfuric acid, phosphoric acid, or hydrobromic acid, etc.) or an organic acid (e.g., oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid, or benzoic acid, etc.); or a salt of the 6-methoxy-2-benzoxazolinone of the present application, which is prepared by reacting the 6-methoxy-2-benzoxazolinone of the present application with a chemically acceptable base, which can be an inorganic base (e.g., sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, or potassium bicarbonate) or an organic base (e.g., trimethylamine, triethylamine, etc.). Further, the pesticidally acceptable salt includes an inorganic salt and an organic salt, the inorganic salt includes at least one of lithium, sodium, potassium, cesium, calcium, magnesium, copper, aluminum, zinc, barium, and quaternary ammonium salt; and the organic salt includes at least one of acetic acid, benzoic acid, salicylic acid, arginine, lysine, glutamic acid, pyroglutamic acid, and azetidine-2-carboxylic acid salt.

[0024] The term "agriculturally acceptable carrier" includes, but is not limited to, a surfactant, which includes an ionic surfactant or a non-ionic surfactant. The surfactant includes an emulsifier, a dispersant or a wetting agent. Among them, the emulsifier can be polyoxyethylene fatty acid ester, polyoxyethylene fatty alcohol ether, polyoxyethylene fatty amine, and commercially available emulsifiers; the dispersant includes sodium lignosulfonate, sodium dithionite, calcium lignosulfonate or methyl naphthalene formaldehyde condensate, etc.; the wetting agent includes sodium lauryl sulfate, sodium dodecylbenzenesulfonate or sodium alkyl naphthalene sulfonate, etc. The agriculturally acceptable carrier includes a solid carrier and / or a liquid carrier. Preferably, the solid carrier includes natural or synthetic clay and silicate, such as natural silica and diatomite; magnesium silicate such as talc; aluminum magnesium silicate such as kaolinite, kaolin, montmorillonite and mica; white carbon black, calcium carbonate, light calcium carbonate; calcium sulfate; limestone; sodium sulfate; amine salts such as ammonium sulfate, hexamethylene diamine. Preferably, the liquid carrier includes water and an organic solvent; when water is used as a solvent or diluent, the organic solvent can be used as an auxiliary agent or an anti-freezing additive. Preferably, the organic solvent includes aromatic hydrocarbons (such as benzene, xylene or toluene, etc.), chlorinated hydrocarbons (such as chlorinated benzene, chloroethylene, trichloromethane or dichloromethane, etc.), aliphatic hydrocarbons (such as petroleum distillate, cyclohexane or light mineral oil, etc.), alcohol solvents (such as isopropyl alcohol, butanol, ethylene glycol, glycerol or cyclohexanol, etc.), ether solvents, ester solvents, ketone solvents (such as acetone, cyclohexanone or N-methyl pyrrolidone, etc.) or dimethylformamide, dimethyl sulfoxide, etc. The antibacterial / viral agent can mix the active ingredient with the liquid carrier and / or the solid carrier during the preparation process, while adding the surfactant (such as emulsifier, dispersant, stabilizer, wetting agent), and other auxiliary agents (such as binder, defoamer, oxidizing agent, etc.) can also be added.

[0025] Example 1: Experiment of preventing and treating cucumber downy mildew

[0026] 1. Experiment of inhibiting cucumber downy mildew spore sac releasing zoospores in vitro

[0027] The seriously diseased leaves were cut from the infected cucumber plants, washed with tap water and then with a brush to remove the dust and other impurities on the leaf surface, and then placed in a culture dish for 24 h in the dark. The sporangia on the leaf lesions were washed with sterile water, and the concentration of the sporangia was adjusted to 50-60 sporangia per field under a 10x10 microscope. A 3% 6-methoxy-2-benzoxazolinone DMSO stock solution was diluted with sterile water to 200 μg / mL, 100 μg / mL, and 20 μg / mL for use. The experiment was set up with 6-methoxy-2-benzoxazolinone at 100 μg / mL, 50 μg / mL, and 10 μg / mL, and water as a control, with 4 treatments and 3 replicates for each treatment. In a 2 mL centrifuge tube, 0.6 mL of the 6-methoxy-2-benzoxazolinone solution at a certain concentration was added, followed by 0.6 mL of the sporangia suspension, which was shaken and then placed in a 4°C refrigerator. After 6 h, 200 sporangia zoospore release rates were investigated under a 10x10 microscope, and the zoospore release inhibition rate was calculated, with the results shown in Table 1.

[0028] Table 1 Effect of 6-methoxy-2-benzoxazolinone on cucumber P. cubensis sporangia releasing zoospores

[0029]

[0030] The results in Table 1 show that 6-methoxy-2-benzoxazolinone has no obvious inhibitory effect on cucumber P. cubensis sporangia releasing zoospores at the tested concentrations, with only 6.32% inhibition at 100 μg / mL.

[0031] 2. Pot experiment for inducing cucumber resistance to P. cubensis

[0032] Pot-grown cucumber seedlings (variety: Xintai Moci) were used for the test. The test agent was 5% 6-methoxy-2-benzoxazolinone soluble liquid, which was diluted with water to 50 mg / L, 10 mg / L, and 1.0 mg / L for treatment, with 1% amino oligosaccharide aqueous solution diluted with water to 50 mg / L as a positive control, and water as a blank control. There were 9 pots of cucumber seedlings for each treatment, with 2 plants per pot, and 3 replicates. The induction treatment was started when the first true leaf of the cucumber was fully expanded, with an induction interval of 4 d, and a total of 3 inductions. The amount of spraying was adjusted to wet the whole leaf without dripping. Three days after the last induction, the cucumber P. cubensis sporangia suspension was sprayed, and the plants were kept moist. After the water control showed obvious disease, the disease index of each treatment was investigated, and the control effect was calculated, with the results shown in Table 2.

[0033] Table 2 Results of 6-methoxy-2-benzoxazolinone in pot experiment for controlling cucumber P. cubensis

[0034] Treatment Disease index (%) Control effect (%) 6-methoxy-2-benzoxazolinone 50.0 mg / L 15.62 72.54 6-methoxy-2-benzoxazolinone 10.0 mg / L 16.69 70.67 6-methoxy-2-benzoxazolinone 1.0 mg / L 23.94 57.93 Amino-oligosaccharide 50.0 mg / L 19.98 64.89 CK 56.90 ——

[0035] The results of Table 2 show that 6-methoxy-2-benzoxazolinone can effectively stimulate the immune system of the cucumber plant to produce disease resistance to Pseudoperonospora cubensis at the tested concentrations. The results of Table 2 also show that the effect of preventing Pseudoperonospora cubensis at a concentration of 10.0 mg / L can reach more than 70%, which is significantly higher than the positive control agent amino oligosaccharide, which has an effect of about 65% on wheat stripe rust at a concentration of 50.0 mg / L.

[0036] Example Two: Inducing Wheat Resistance to Stripe Rust Potted Plant Experiment

[0037] Potted wheat seedlings (variety: Mingxian 169) were used for testing. The tested agent was 5% 6-methoxy-2-benzoxazolinone soluble liquid, which was diluted with water to 50 mg / L, 10 mg / L, and 1.0 mg / L for treatment. A 1% amino oligosaccharide aqueous solution diluted with water to 50 mg / L was used as the positive control, and water was used as the blank control. There were 6 pots of wheat seedlings for each treatment, with 12-15 plants per pot, and the experiment was repeated 3 times. When the wheat leaves grew to 1 leaf 1 heart, the induction treatment was started, with an induction interval of 4 days, and a total of 3 inductions. The spraying amount was full plant wetting, and the liquid did not drip. Three days after the last induction, the wheat seedlings were sprayed with Puccinia striiformis spore cyst suspension. After the water control showed obvious disease, the disease index of each treatment was investigated, and the control effect was calculated, and the results are shown in Table 3.

[0038] Table 3 6-methoxy-2-benzoxazolinone prevents wheat stripe rust potted plant experiment results

[0039] Treatment Disease index (%) Control effect (%) 6-methoxy-2-benzoxazolinone 50.0 mg / L 12.08 78.14 6-methoxy-2-benzoxazolinone 10.0 mg / L 13.55 75.49 6-methoxy-2-benzoxazolinone 1.0 mg / L 22.18 59.88 Amino-oligosaccharide 50.0 mg / L 17.68 68.01 CK 55.28 ——

[0040] The results of Table 3 show that 6-methoxy-2-benzoxazolinone can effectively stimulate the immune system of the wheat plant to produce disease resistance to Puccinia striiformis at the tested concentrations. At a concentration of 10.0 mg / L, the effect of preventing Puccinia striiformis can reach more than 75%, which is significantly higher than the positive control agent amino oligosaccharide, which has an effect of 68% on wheat stripe rust at a concentration of 50.0 mg / L.

[0041] Example Three: Inducing Tobacco Resistance to Common Mosaic Virus Disease Potted Plant Experiment

[0042] Potting tobacco (variety: Yunyan 87) is induced to grow to 6 leaf stage and then treated with pesticide. The tested pesticide is 5% 6-methoxy-2-benzoxazolinone soluble liquid, which is diluted with water to 50 mg / L and 10 mg / L. The water-diluted 1% amino oligosaccharide solution is 50 mg / L as a positive control, and the water is a blank control. There are 10 pots of tobacco seedlings in each treatment, and each pot contains one plant, which is repeated three times. The induction interval is 4 days, and a total of 3 times of induction is performed. The spraying amount is determined by the whole plant tobacco seedling wetting, and the pesticide solution does not drip. On the third day after the last induction and pesticide treatment, the tobacco mosaic virus is inoculated by using the conventional juice rubbing method. The virus inoculum is obtained by grinding the infected Tobacco Mosaic Virus (TMV) of Nicotiana tabacum leaf and PBS buffer at a ratio of 1:20 (w / v) with a small amount of emery and then filtering with 4 layers of sterilized gauze. After the water control is obviously diseased, the disease index of each treatment is investigated, and the control effect is calculated. The results are shown in Table 4.

[0043] Table 4: Results of 6-methoxy-2-benzoxazolinone in preventing and treating tobacco mosaic virus disease in potting experiments

[0044] Treatment Disease index (%) Control effect (%) 6-methoxy-2-benzoxazolinone 50.0 mg / L 9.26 69.09 6-methoxy-2-benzoxazolinone 10.0 mg / L 13.87 53.68 Amino-oligosaccharide 50.0 mg / L 8.64 71.17 CK 29.96 ——

[0045] The results of Table 4 show that 6-methoxy-2-benzoxazolinone can effectively stimulate the immune system of tobacco plants at the tested concentration, and produce disease resistance to tobacco mosaic virus. At a concentration of 50.0 mg / L, the control effect can reach 69%, which is comparable to the control effect of the commercial pesticide amino oligosaccharide at the same concentration.

[0046] As can be seen from the above experimental results, 6-methoxy-2-benzoxazolinone has broad-spectrum and high efficiency in preventing and treating crop diseases, and can effectively prevent and control various important crop diseases, especially for preventing and treating cucumber downy mildew, wheat stripe rust, and tobacco mosaic virus disease. The effective prevention and control concentration is only 1.0 mg / L-10.0 mg / L.

[0047] The preferred embodiments of the present application are described in detail above, but the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solutions of the present application, and these simple modifications all belong to the protection scope of the present application.

[0048] In addition, it should be noted that each specific technical feature described in the above specific embodiments can be combined in any appropriate manner without contradiction. In order to avoid unnecessary repetition, various possible combinations are not described again in the present application.

[0049] Moreover, the various embodiments disclosed herein can be combined in any combination, provided such combinations do not violate the spirit of the application, which is to provide a method and system for providing a user with a personalized experience.

Claims

1. The use of 6-methoxy-2-phenylazolinone or a pesticide-acceptable salt thereof, or an agricultural antibacterial / viral agent containing 6-methoxy-2-phenylazolinone or a pesticide-acceptable salt thereof, characterized in that, Used to prevent and control crop pathogens or viruses, or to prevent and control crop diseases; The pathogens or viruses mentioned are Puccinia striiformis west.f.sp.tritici (wheat stripe rust), Pseudoperonspora cubensis (cucumber downy mildew), and Tobcacco Mosaic Virus (tobacco common mosaic virus). The crop diseases mentioned are wheat stripe rust, cucumber downy mildew, and tobacco common mosaic virus.

2. A method for preventing and controlling crop diseases, characterized in that... Applying 6-methoxy-2-phenylazolinone or its agronomically acceptable salts, or agricultural antibacterial / viral agents containing 6-methoxy-2-phenylazolinone or its agronomically acceptable salts, to crops; The crop diseases mentioned are wheat stripe rust, cucumber downy mildew, and tobacco common mosaic virus.

3. The use according to claim 1, or the method according to claim 2, characterized in that, The pesticide-acceptable salts are either inorganic or organic.

4. The use or method according to claim 3, characterized in that, The inorganic salt is at least one of lithium, sodium, potassium, cesium, calcium, magnesium, copper, aluminum, zinc, barium, and quaternary ammonium salts; the organic salt is at least one of acetic acid, benzoic acid, salicylic acid, arginine, lysine, glutamic acid, pyroglutamic acid, and aziridine-2-carboxylate.

5. The use according to claim 1, or the method according to claim 2, characterized in that, The antibacterial / viral agent further comprises a pesticide-acceptable carrier.

6. The use or method according to claim 5, characterized in that, In the antibacterial / viral agent, 6-methoxy-2-benzolinone or its pesticide-acceptable salt is dissolved or dispersed in a carrier to formulate a soluble liquid, soluble powder, emulsifiable concentrate, suspension concentrate, water suspension, microemulsion, emulsion, water emulsion, powder, wettable powder, granule, water-dispersible granule or capsule formulation.

7. The use or method according to claim 6, characterized in that, In the antibacterial / viral agent, 6-methoxy-2-benzolinone or a pesticide-acceptable salt thereof is dissolved or dispersed in a carrier to formulate a dimethyl sulfoxide liquid.

8. The use according to claim 1, or the method according to claim 2, characterized in that, The concentration of the active ingredient 6-methoxy-2-benzolinone is 1.0 mg / L-50.0 mg / L.

9. The use or method according to claim 8, characterized in that, The concentration of the active ingredient 6-methoxy-2-benzolinone is 1.0 mg / L-10.0 mg / L.

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