A herbicidal composition containing 5-phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester

Abstract

This invention discloses a herbicidal composition containing ethyl 5-phenyl-4,5-dihydroisoxaazole-3-carboxylate and component B. Component B is selected from one or more of nicosulfuron, sulfadiazine, formamide sulfur, quizalofop-p-ethyl, cyclosulfonamide, isoxaflutole, dicamba, benzoxazine, 2,4-D and its salts, 2,4-D and its salts, 2,4-D isooctyl ester, and mesosulfuron-methyl. The composition of this invention exhibits good synergistic effects, good crop safety, and broad application prospects.

Description

[0001] This application is a divisional application of the invention patent application filed on October 30, 2023, with application number 202311413561.X and invention title "A herbicidal composition containing ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate". Technical Field

[0002] This invention belongs to the field of pesticides, specifically relating to a class of herbicidal compositions containing ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and their applications. Technical Background

[0003] Some herbicides can cause phytotoxicity to crops due to improper application methods, inappropriate application times, and the properties of the herbicides themselves. Examples include sulfonylurea herbicides such as nicosulfuron, sulfadiazine, and formamide sulfonium; triketone herbicides such as cyclosulfonamide; isoxazole herbicides such as isoxaflutole; aryloxyphenoxypropionic acid herbicides such as pinoxaflutole and methylparaben; and aryl carboxylic acid herbicides such as dicamba. Adding safeners is one of the most important ways to solve the problem of herbicide phytotoxicity.

[0004] Currently, the above-mentioned herbicides mainly reduce phytotoxicity by adding safeners such as ethyl bis(oxazolyl) or cyclopropanesulfonamide.

[0005]

[0006] Cyclopropanesulfonamide,

[0008]

[0009] Ethyl dibenzoxazole acid.

[0011] However, studies have found that the effect of ethyl bis(phenyloxazo)ate or cyclopropanesulfonamide in combination with herbicides is generally to reduce the phytotoxicity of herbicides. During the development and research process, the applicant discovered that ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate is not only a good herbicide safener, but also exhibits a synergistic effect with specific herbicide combinations within a certain proportion range. The structure of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate is as follows:

[0012]

[0013] 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester. Summary of the Invention

[0014] This invention provides a class of herbicidal compositions containing ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate that are safer and more crop-friendly. The compositions of this invention have a synergistic effect while having good safety, and have broad application prospects.

[0015] Specifically, the present invention achieves a safer crop effect for the herbicidal composition through the following technical solution, while the composition also exhibits a synergistic effect. The herbicidal composition of the present invention contains ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and component B, wherein component B is a herbicide selected from one or more of nicosulfuron, sulfadiazine, formamide sulfonamide, quizalofop-p-ethyl, cyclosulfonamide, isoxaflutole, dicamba, benzoxazine, 2,4-D and its salts, 2,4-D and its salts, 2,4-D isooctyl ester, and mesosulfuron-methyl.

[0016] The present invention also provides a formulation containing the herbicidal composition of the present invention.

[0017] The present invention also provides the application of the herbicidal composition or its formulation in controlling weeds in agriculture, forestry and horticulture.

[0018] Beneficial effects of the present invention

[0019] 1. The combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and herbicides shows superior crop safety.

[0020] 2. The specific herbicidal composition of the present invention containing ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate has a good synergistic effect. Detailed Implementation

[0021] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention. Unless otherwise expressly stated, throughout the specification and claims, the term "comprising" or its variations such as "including" or "comprising of," etc., will be understood to include the stated components or steps, without excluding other substances or steps.

[0022] Furthermore, to better illustrate the present invention, numerous specific details are provided in the following detailed embodiments.

[0023] Those skilled in the art will understand that the present invention can be practiced even without certain specific details. In some embodiments, materials, methods, and means well known to those skilled in the art are not described in detail in order to highlight the spirit of the invention.

[0024] The terms “prevention” and “elimination” used in this invention are synonyms.

[0025] The present invention first provides a herbicidal composition containing ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and component B, wherein the herbicide is selected from one or more of nicosulfuron, sulfadiazine, formamide sulfadiazine, quizalofop-p-ethyl, cyclosulfonamide, isoxaflutole, dicamba, benzoxazine, 2,4-D and its salts, 2,4-D and its salts, 2,4-D isooctyl ester and mesosulfuron-methyl.

[0026] Preferably, the herbicide weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate to component B in the composition is 1:1 to 99 or 1 to 99:1, more preferably 1:60 to 20:1.

[0027] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate to nicosulfuron in the composition is 1:15-1:1, more preferably 1:10, 1:6, or 1:4.

[0028] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate to sulfadiazine in the composition is 1:10-1:1, more preferably 1:8, 1:4, or 1:2.

[0029] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate to formamide sulfonamide in the composition is 1:10-1:1, more preferably 1:6, 1:4, or 1:1.

[0030] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and quizalofop-p-ethyl in the composition is 1:15-1:1, more preferably 1:10, 1:5, or 1:2.

[0031] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate to cyclosulfonone in the composition is 1:15-1:1, more preferably 1:10, 1:5, or 1:2.

[0032] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate to isoxazolone in the composition is 1:10-1:1, more preferably 1:6, 1:2, or 1:1.

[0033] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and dicamba in the composition is 1:60-1:5, more preferably 1:60, 1:30, or 1:15.

[0034] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate to benzoxazine in the composition is 1:15-1:1, more preferably 1:10 or 1:5.

[0035] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and 2,4-methylchloro and its salt in the composition is 1:30-1:1, more preferably 1:20 or 1:10.

[0036] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and 2,4-drop and its salt in the composition is 1:30-1:5, more preferably 1:20, 1:15, or 1:12.

[0037] Preferably, the weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and 2,4-diisooctyl ester in the composition is 1:30-1:5, more preferably 1:20, 1:15, or 1:10.

[0038] The present invention also discloses a formulation containing the herbicidal composition of the present invention, wherein the content of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate is 1-99%, and the content of component B is 1-99%. Preferably, the content of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate is 1-80%, and the content of component B is 1-80%; more preferably, the content of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate is 1-30%, and the content of component B is 1-60%.

[0039] The compositions or formulations described above in this invention can be prepared into conventional dosage forms in this field as needed. These dosage forms are prepared using conventional techniques in this field. The dosage forms are agriculturally acceptable and include powders, wettable powders, soluble powders / granules, emulsifiable concentrates, aqueous solutions, granules, water-dispersible granules, suspensions, dispersible oil suspensions, and water-emulsions.

[0040] The above-mentioned herbicidal composition incorporates suitable adjuvants during the preparation of a suitable formulation. These adjuvants include one or more of the following: emulsifiers, wetting / penetrating agents, dispersants, stabilizers, thickeners, disintegrants, antifreeze agents, preservatives, defoamers, binders, fillers / carriers, solvents / cosolvents, etc.

[0041] The emulsifiers are preferably nonylphenol polyoxyethylene ether, fatty alcohol polyoxyethylene ether, fatty amine polyoxyethylene ether, alkyl glycoside, styrene-phenol polyoxyethylene ether (agricultural emulsion 601#, 602#, 603#, 604#), styrene-phenol paraformaldehyde condensate (agricultural emulsion 401#, 402#), styrene-phenol polyoxypropylene polyoxyethylene copolymer (agricultural emulsion 33#, 34#, 1601#, 1602#), castor oil polyoxyethylene ether, polyoxyethylene oleate, ethylene oxide / propylene oxide co-ether, and so on. One or more of the following: pear ester ethers (Span-20, Span-40, Span-60, Span-65, Span-80, Span-85, Tween-20, Tween-40, Tween-60, Tween-65, Tween-80, Tween-85), polyglycerol fatty acid esters, calcium dodecylbenzene sulfonate, polyoxyethylene ether sulfate salts, polyoxyethylene ether phosphate salts, and nonylphenol polyoxyethylene ether formaldehyde condensate (agricultural emulsion 700#).

[0042] The preferred wetting agents / penetrating agents are fatty alcohol ethers (such as isomeric alcohol ethers 1300 series, MOA series, penetrant JFC, emulsifier AEO, etc.), alkylphenol polyoxyethylene ethers (such as TX, OP, NP series, etc.), fatty amine polyoxyethylene ethers (such as AC-1800 series, AC-1200 series, AN-1800 series, etc.), alkyl glycosides (C8-C10 alkyl glycosides, C12-C14 alkyl glycosides, C8-C14 alkyl glycosides, etc.), and polyarylates. One or more of the following: alkylphenol polyoxyethylene ether (such as agricultural emulsion 600#, agricultural emulsion 400#, agricultural emulsion 33#, agricultural emulsion 34#), castor oil polyoxyethylene ether (such as BY-110, BY-125, BY-140, etc.), calcium dodecylbenzene sulfonate, sodium α-alkenyl sulfonate, sodium salt of fatty alcohol ether sulfate AES, sodium alkyl succinate sulfonate (such as fast T, etc.), polycyclic aromatic hydrocarbon formaldehyde condensate sulfonate or alkyl aromatic hydrocarbon sulfonate (such as dispersant NNO, pull-opening powder BX, etc.).

[0043] The dispersant is preferably naphthalene or alkylnaphthalene formaldehyde condensate sulfonate (such as dispersant N), lignin sulfonate, phosphate salt (such as 601PT), polyoxyethylene ether sulfate salt, sodium succinate diester sulfonate, polycarboxylate, fatty alcohol polyoxypropylene polyoxyethylene ether, polyoxyethylene polyether block copolymer, etc.

[0044] The stabilizer is preferably one or more of the following: phosphite, epichlorohydrin, epoxidized soybean oil, epoxidized linseed oil, BHA, BHT, etc.

[0045] The thickener is preferably one or more of the following: sodium chloride, ammonium chloride, ammonium sulfate, magnesium aluminum silicate, starch, xanthan gum, agar, hydroxymethyl cellulose, hydroxypropyl methyl cellulose, organobentonite, diatomaceous earth, and polyvinyl alcohol.

[0046] The preferred disintegrant is one or more of the following: sodium carboxymethyl starch, croscarmellose sodium, croscarmellose cellulose, modified starch, croscarmellose polyvinylpyrrolidone, magnesium aluminum silicate, sodium alginate, etc.

[0047] The antifreeze is preferably one or more of ethylene glycol, propylene glycol, glycerol, polyethylene glycol, urea, etc.

[0048] The preservative is preferably one or more of benzoic acid, sorbic acid, p-hydroxybenzoic acid, hydroquinone, etc.

[0049] The defoamer is preferably one or more of the following: propanol, butanol, tributyl phosphate, polyether surfactants, polyethylene glycol fatty acid esters, mineral oil, and siloxane oil.

[0050] The binder is selected from one or more of starch, gelatin and gum arabic, povidone, sucrose, glucose, and dextrin.

[0051] The carrier / filler is preferably one or more of the following: diatomaceous earth, attapulgite, bentonite, zeolite, sepiolite, kaolin, clay, silica, light calcium carbonate, starch, magnesium stearate, talc.

[0052] The solvent / co-solvent is preferably one or more of the following: soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, palm oil, peanut oil, castor oil or methylated vegetable oil, solvent naphtha, liquid paraffin oil, benzene, toluene, xylene, naphthalene, methanol, ethanol, ethylene glycol, isopropanol, cyclohexanol, cyclohexanone, acetonitrile, acetone, dimethyl sulfoxide, N-methylpyrrolidone, propionic acid alcohol, acetate, dichloromethane, chloroform, cresol, etc.

[0053] The herbicidal composition of this invention can be used to control unwanted plants in crop fields. The crops include: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beets, rapeseed, sunflowers, sugarcane, tobacco, eggplant, tomato, bell peppers, chili peppers, potatoes, cucumbers, pumpkins, zucchini, watermelons, cantaloupes, Japanese radishes, white radishes, horseradishes, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, garland chrysanthemum, artichokes, lettuce, scallions, onions, garlic, or asparagus, carrots, parsley, celery, parsnip, spinach, Swiss chard, apples, pears, papayas, peaches, plums, nectarines, prunes, cherries, apricots, prunes, tangerines, oranges, lemons, limes, grapefruits, chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, or macadamia nuts, grapes, persimmons, olives, loquats, bananas, coffee, dates, coconut palms, oil palms, etc. The undesirable plants include annual or perennial weeds and resistant weeds, with particularly preferred species being barnyard grass, crabgrass, foxtail grass, amaranth, velvetleaf, chickweed, cocklebur, sedge, sedge, water hyacinth, purslane, and duckweed. The composition of this invention exhibits excellent safety, particularly for corn, wheat, rice, soybeans, and rapeseed.

[0054] The present invention will be described in detail below through embodiments. In the following embodiments: unless otherwise specified, all raw materials used are commercially available products. Percentages in the embodiments are weight percentages. Specific Implementation

[0055] Example 1: 20% Nicosulfuron Dispersible Oil Suspension

[0056] Nicosulfuron 20%

[0057] 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester 5%

[0058] Calcium dodecylbenzenesulfonate (70% isobutanol solution) 3%

[0059] xanthan gum 2%

[0060] Methyl oleate replenished to 100%.

[0061] Preparation method: Prepare the measured components, then add nicosulfuron, ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate, xanthan gum, part of calcium dodecylbenzenesulfonate (70% isobutanol solution) and part of methyl oleate to a sand mill in sequence. After 2 hours, stop the sand milling, transfer the mixture to a mixer, add the remaining calcium dodecylbenzenesulfonate (70% isobutanol solution) and methyl oleate, and mix evenly.

[0062] Implementation List 2: 25% Sulfadiazine Water Dispersible Granules

[0063] Sulfadiazine 25%

[0064] 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester 12.5%

[0065] Agricultural dairy product 601# 3%

[0066] Calcium dodecylbenzenesulfonate 2%

[0067] 1% Magnesium Aluminum Silicate

[0068] 1% urea

[0069] Starch replenishment to 100%

[0070] Preparation method: Prepare the measured components, add sulfadiazine, methyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate, agricultural emulsion 601#, calcium dodecylbenzenesulfonate, and magnesium aluminum silicate to water and grind, add urea and starch and then transport to a spray drying tower for spray granulation.

[0071] Example 3: 3% Formamide Sulfonate Dispersible Oil Suspension

[0072] 3% formamide sulfonamide

[0073] 3% 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester

[0074] Span-20 3%

[0075] Quick T 2%

[0076] 1% polyethylene glycol

[0077] Soybean oil replenished to 100%

[0078] Preparation method: Prepare the measured components, and then add formamide sulfonamide, ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate, Span-20, Quick T, polyethylene glycol and soybean oil into a sand mill in sequence. Stop the sand milling after 2 hours to obtain a dispersible oil suspension.

[0079] Example 4: 10% quizalofop-p-ethyl emulsifiable concentrate

[0080] 10% of quizalofop-p-ethyl

[0081] 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester 5%

[0082] Castor oil polyoxyethylene ether 5%

[0083] 3% Ethylene glycol

[0084] Solvent naphtha replenished to 100%.

[0085] Preparation method: Prepare the measured components, add most of the solvent naphtha into the mixing vessel, turn on the stirrer (stirring speed 60~80r / min), add quizalofop-p-ethyl, 5-phenyl-4,5-dihydroisoxazole-3-carboxylic acid propyl ester, castor oil polyoxyethylene ether and ethylene glycol in sequence, and then add the remaining solvent naphtha. After stirring for 1-2 hours, the emulsifiable concentrate is obtained.

[0086] Example 5: 8% Cyclosulfonone Dispersible Oil Suspension

[0087] Cyclosulfonone 8%

[0088] 4% 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester

[0089] Agricultural Milk 401# 2%

[0090] Calcium dodecylbenzenesulfonate (70% isobutanol solution) 3%

[0091] 1% Hydroxypropyl methylcellulose

[0092] Solvent naphtha replenished to 100%.

[0093] Preparation method: Prepare the measured components, and then add cyclosulfonone, ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate, agricultural emulsion 401#, calcium dodecylbenzenesulfonate (70% isobutanol solution), hydroxypropyl methylcellulose and solvent naphtha into a sand mill in sequence. Stop the sand mill after 2 hours to obtain a dispersible oil suspension.

[0094] Example 6: 20% isoxaflutole suspension

[0095] Isoxazolidin 20%

[0096] 20% 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester

[0097] Agricultural Milk 1601# 3%

[0098] NNO 3%

[0099] 1% hydroxymethylcellulose

[0100] 1% epichlorohydrin

[0101] Tributyl phosphate 0.5%

[0102] Water replenished to 100%

[0103] Preparation method: Prepare the measured components, add isoxazolidinone, 5-phenyl-4,5-dihydroisooxazol-3-carboxylic acid isopropyl ester, agricultural emulsion 1601#, NNO, hydroxymethyl cellulose, epichlorohydrin, tributyl phosphate and water into a high-speed shear mill for pre-dispersion for 30 min, and then send it to a sand mill for sand milling for 2 h to obtain a suspension.

[0104] Example 7: 50% Dicamba Soluble Solution

[0105] 50% dicamba

[0106] 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester 5%

[0107] Tween-20 5%

[0108] Ethanol replenished to 100%

[0109] Preparation method: Prepare the measured components, and add ethanol, dicamba, 5-phenyl-4,5-dihydroisoxazole-3-carboxylic acid and Tween-20 to the mixing vessel in sequence. Stir and mix evenly to obtain the soluble solution.

[0110] Example 8: 10% Benzophenone Dispersible Oil Suspension

[0111] Benzophenone 10%

[0112] 2% 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester

[0113] Calcium dodecylbenzenesulfonate (70% isobutanol solution) 4%

[0114] 1% polyethylene glycol

[0115] Methyl oleate replenished to 100%.

[0116] Preparation method: Prepare the measured components, and then add benzoxazine, ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate, calcium dodecylbenzenesulfonate (70% isobutanol solution), polyethylene glycol and methyl oleate into a sand mill in sequence. Stop the sand milling after 2 hours to obtain a dispersible oil suspension.

[0117] Example 9: 60% 2,4-D dimethylamine salt soluble granules

[0118] 2,4-D dimethylamine salt 60%

[0119] 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester 5%

[0120] Castor oil polyoxyethylene ether 3%

[0121] Quick T 2%

[0122] 2% glucose

[0123] Epoxidized soybean oil 2%

[0124] 100% replenishment of silica.

[0125] Preparation method: Prepare the measured components, add the powdered material to the feeder, add the liquid material to the liquid supply device, and prepare soluble granules by fluidized bed granulation.

[0126] Example 10: 55% 2,4-D isooctyl ester emulsifiable concentrate

[0127] 2,4-D isooctyl ester 55%

[0128] 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester 5.5%

[0129] Span-40 4%

[0130] Castor oil polyoxyethylene ether 2%

[0131] Toluene 2%

[0132] Liquid paraffin oil replenished to 100%.

[0133] Preparation method: Prepare the measured components, add most of the liquid paraffin oil to the mixing vessel, turn on the stirrer (stirring speed 60~80r / min), add the weighed other components in sequence, and then add the remaining liquid paraffin oil. After stirring for 2 hours, the emulsion is obtained.

[0134] Example 11: 60% 2,4-chlorodimethylamine saline solution

[0135] 60% of 2,4-chlorodimethylamine salt

[0136] 6% 5-Phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester

[0137] Calcium dodecylbenzenesulfonate (70% isobutanol solution) 5%

[0138] 1% Ethylene glycol

[0139] 1% benzoic acid

[0140] Water replenished to 100%

[0141] Preparation method: Prepare the measured components, and add 2,4-methylchlorodimethylamine salt, 5-phenyl-4,5-dihydroisoxazole-3-carboxylic acid, calcium dodecylbenzenesulfonate (70% isobutanol solution), ethylene glycol, benzoic acid and water to the mixing vessel in sequence. Stir and mix evenly to obtain the aqueous solution.

[0142] Bioactivity test

[0143] 1. Safety test

[0144] 1.1 Test Drugs

[0145] Herbicides such as nicosulfuron, sulfosulfuron, formamide sulfuron, quizalofop-P-ethyl, cyclosulfonamide, isoxaflutole, dicamba, benzoxazine, 2,4-D, 2,4-D isooctyl ester, etc., are purchased from the market. Ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate, ethyl bis(phenyloxazole) acid, and cyclopropanesulfonamide, which act as safeners, are synthesized in our laboratory.

[0146] 1.2 Drug Preparation

[0147] Weigh out a certain amount of herbicide and safener compounds, dissolve them in acetone, and dilute them with a 0.1% Tween 80 aqueous solution. The specific dosage and ratio are shown in Table 1-3. Unless otherwise specified, the dosage data in Table 1-3 represent the dosage of the herbicide active ingredient or safener compound.

[0148] 1.3 Experimental Methods

[0149] Take well-drained, sieved soil with a permeable organic matter content of 2.5% and a pH of 7. Fill pots 4 / 5 full with the soil and water from the top until the soil is completely moist. Sow 30 crop seeds evenly on the soil surface and cover with about 1.0 cm of soil. Transfer to a greenhouse and cultivate at 20±2℃. For dryland crops such as corn and wheat, water is added by drip irrigation from the bottom of the pot. For paddy crops such as rice, water is added by irrigation from the top of the pot until saturation. After emergence, thin the seedlings and transplant them, leaving 10 plants of similar growth in each pot and evenly distributing them. Spray the pesticide when the crops are at the 3-4 leaf stage, with a spray volume of 350 L / ha. Each treatment has 4 replicates, and a control group without herbicides and safeners is set up. Observe and record the pesticide damage after 14 days.

[0150] Phytotoxicity effect is indicated as follows: 0 indicates safety and no phytotoxicity; 1~10 indicates no obvious phytotoxicity; 11~30 indicates slight phytotoxicity; 31~50 indicates moderate phytotoxicity; >50 indicates severe phytotoxicity (refer to standard NY / T 1155.8-2007).

[0151] Table 1. Safety test results of herbicide compositions on corn

[0152]

[0153]

[0154] Table 2. Safety test results of herbicidal compositions on rice

[0155]

[0156] Table 3. Safety test results of herbicidal compositions on wheat

[0157]

[0158] 2. Bioassay of weed targets

[0159] 2.1 Test Drugs

[0160] Herbicides such as nicosulfuron, sulfosulfuron, formamide sulfuron, quizalofop-P-ethyl, cyclosulfonamide, isoxaflutole, dicamba, benzoxazine, 2,4-D, 2,4-D isooctyl ester, and mesosulfuron-methyl were purchased from the market, while ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate, ethyl bis(phenyloxazole) acid, and cyclopropanesulfonamide were synthesized in our laboratory.

[0161] 2.2 Preparation of the medicine

[0162] Weigh a certain amount of the above raw materials, dissolve them in acetone, and dilute them with a 0.1% Tween 80 aqueous solution for later use. The specific usage and ratio are shown in Table 4-15. Unless otherwise specified, the usage data in Table 4-15 represent the amount of herbicide active ingredient or ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate, ethyl bis(phenyloxazole)ate, and cyclopropanesulfonamide compound.

[0163] 2.3 Experimental Methods

[0164] Take well-drained, sieved, and air-dried soil with a permeable organic matter content of 2.5% and a pH of 7. Fill pots 4 / 5 full with the soil and water from the top until the soil is completely moist. Sow 30 weed seeds evenly on the soil surface, cover with about 1.0 cm of soil, and move to a greenhouse for cultivation at 20±2℃. For dryland weeds, water the pots by drip irrigation from the bottom; for paddy field weeds, water the pots by irrigation from the top until saturated. After emergence, thin and transplant, leaving 10 weeds of similar growth per pot, evenly distributed. Spray the herbicide when the weeds are at the 3-4 leaf stage, at a rate of 350 L / ha. Each treatment has 4 replicates, and a control group is included that does not contain herbicides and ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate. After 14 days, observe the weed symptoms and growth inhibition, and weigh the fresh weight of the above-ground parts of the weeds.

[0165] Calculate the fresh weight inhibition rate (%).

[0166] Fresh weight inhibition rate (%) = (control fresh weight - treatment fresh weight) / control fresh weight × 100.

[0167] 2.4 Evaluation Methods for Synergistic Effects

[0168] The Gowing method was used to evaluate the synergistic effect of herbicides, and the formula is as follows:

[0169] ,

[0170] In the formula, X is the fresh weight inhibition rate when the herbicide dosage is P; Y is the fresh weight inhibition rate when the dosage of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate is Q; E0 is the theoretical control efficacy when the herbicide dosage is P + the dosage of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate is Q; and E is the actual control efficacy after the herbicide and ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate are mixed in the above proportion.

[0171] Evaluation criteria: When E-E0 > 10%, it indicates a synergistic effect; when E-E0 is between ±10%, it indicates an additive effect; and when E-E0 < -10%, it indicates an antagonistic effect.

[0172] Table 4. Bioassay data for ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate or ethyl bis(phenyloxazole)ate or cyclopropionamide and nicosulfuron-methyl combinations.

[0173]

[0174] Table 5. Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and sulfadiazine.

[0175]

[0176] Table 6. Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and formamide sulfonamide.

[0177]

[0178] Table 7. Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and cyclosulfonone.

[0179]

[0180] Table 8. Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and isoxazolidinone.

[0181]

[0182] Table 9 Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and dicamba.

[0183]

[0184] Table 10 Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and benzoxazine.

[0185]

[0186] Table 11 Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and quizalofop-p-ethyl.

[0187]

[0188] Table 12 Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and 2,4-methylchloro

[0189]

[0190] Table 13 Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and 2,4-D.

[0191]

[0192] Table 14 Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and 2,4-D isooctyl ester

[0193]

[0194] Table 15 Bioassay data for the combination of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and mesosulfuron-methyl

[0195]

[0196] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the protection scope of the present invention.

[0197] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, the present invention will not describe the various possible combinations separately.

[0198] Furthermore, various different embodiments of the present invention can be combined in any way, as long as they do not violate the spirit of the present invention, they should also be regarded as the content disclosed by the present invention.

Claims

1. A herbicidal composition, characterized in that, A herbicide comprising ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate and component B, wherein the herbicide component B is formamidesulfuron.

2. The herbicidal composition according to claim 1, characterized in that, The weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate to formamide sulfonamide is 1:1 to 99 or 1 to 99:1, more preferably 1:60 to 20:

1.

3. The herbicidal composition according to claim 2, characterized in that, The weight ratio of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate to formamide sulfonamide in the composition is 1:10-1:1, preferably 1:6, 1:4, or 1:

1.

4. A herbicidal composition formulation, characterized in that, It contains the composition according to any one of claims 1-3 and a pesticide-acceptable adjuvant.

5. The formulation according to claim 4, characterized in that, The content of ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate is 1-99%, and the content of component B is 1-99%.

6. The formulation according to claim 4 or 5, characterized in that, It can be formulated into agriculturally acceptable dosage forms.

7. The formulation according to claim 6, characterized in that, The dosage form is selected from one of the following: powder, wettable powder, soluble powder / granule, emulsifiable concentrate, aqueous solution, granule, water-dispersible granule, suspension concentrate, dispersible oil suspension, and water emulsion.

8. The use of the composition according to any one of claims 1-3 or the formulation according to any one of claims 4-7 in the control of weeds in crop fields.

9. The application according to claim 8, characterized in that, The crops mentioned are one of the following: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beets, rapeseed, sunflowers, sugarcane, tobacco, eggplant, tomato, bell pepper, chili pepper, potato, cucumber, pumpkin, zucchini, watermelon, cantaloupe, Japanese radish, white radish, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, garland chrysanthemum, artichoke, lettuce, scallion, onion, garlic, or asparagus, carrot, parsley, celery, parsnip, spinach, Swiss chard, apple, pear, papaya, peach, plum, nectarine, plum, cherry, apricot, prune, Wenzhou mandarin orange, orange, lemon, lime, grapefruit, chestnut, walnut, hazelnut, almond, pistachio, cashew or macadamia nut, grape, persimmon, olive, loquat, banana, coffee, date palm, coconut palm, and oil palm; preferably corn, wheat, rice, soybeans, or rapeseed.

10. The application according to claim 9, characterized in that, The weeds mentioned are annual or perennial weeds and resistant weeds, with annual or perennial grass weeds, broadleaf weeds and sedges being preferred; barnyard grass, crabgrass, foxtail grass, amaranth, velvetleaf, chickweed, cocklebur, sedge, sedge, water hyacinth, purslane and duckweed being particularly preferred.

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