Weeding compound and application thereof

Abstract

The invention discloses a weeding compound and application thereof, and belongs to the field of pesticides. The weeding compound is formed by compounding three herbicides, namely pyribenzoxim, halauxifen-methyl and propanil. According to the weeding compound containing the pyribenzoxim, the halauxifen-methyl and the propanil, through the combined action of the pyribenzoxim, the halauxifen-methyl and the propanil, the compound herbicide has a good weeding effect and has good social and ecological benefits.

Description

TECHNICAL FIELD

[0001] The present application belongs to the field of pesticide dosage forms, and particularly relates to a pyribenzoxim, flupyradifurone and propanil herbicidal compound and application thereof. BACKGROUND

[0002] Pyribenzoxim, English name: Pyribenzoxim, is a novel oxime ester compound, which is a broad-spectrum selective post-emergence herbicide, mainly used for weed control in rice fields. The chemical name is: 6-bis (4, 6-dimethoxy pyrimidine-2-yl oxy) benzoyl) oxime benzophenone, molecular formula C 32 H 27 N5O8, the mechanism of action is similar to that of sulfonylurea and imidazole acetone herbicides, which are all acetyl lactate synthase (ALS) inhibitors. It has selective super-high post-emergence herbicidal activity on rice, common wheat and bentgrass, has no pre-emergence herbicidal activity, and is used for controlling various gramineous weeds and broadleaf weeds such as barnyard grass, giant foxtail, and red salvia, and has high safety to rice.

[0003] Flupyradifurone, English name: Florpyrauxifen-benzyl, CAS: 1390661-72-9, molecular formula: C 20 H 14 Cl2F2N2O3. It is an aryl pyridine carboxylate herbicide developed by Dow AgroSciences, which belongs to synthetic hormones and plays a role by interfering with the plant growth regulation system. Once combined with the target, it will trigger a sharp increase in intracellular life activities, leading to abnormal growth of sensitive plants such as stem bending and tissue swelling, and eventually leading to death. This type of herbicide not only has excellent absorption and transmission performance, consistent symptom development, rapid onset, but also can adapt to various cultivation methods. At the same time, due to the complexity of the target site, plants are not easy to develop resistance.

[0004] Propanil, English name: propanil, chemical name: N-3, 4-dichlorophenyl propionamide, belongs to amide type high selective contact herbicide, mainly used in seedbed or direct seeding field, and is a special herbicide for controlling barnyard grass. Propanil is almost not translocated in the plant body, and only works at the contact site. Its mechanism of action is multifaceted, not only destroying photosynthesis, but also inhibiting respiration and oxidative phosphorylation, and interfering with nucleic acid and protein synthesis, etc. Thus, the physiological functions of sensitive plants are affected, and the water loss is accelerated, the leaves are gradually dried, and finally the plants die.

[0005] At present, the resistance of weeds in rice fields is becoming more and more serious, especially the resistant barnyard grass and resistant leafflower, which are very difficult to control. The formulations prepared by the above three kinds of agents alone cannot well solve the problem of resistant gramineous weeds.

[0006] Currently, there are no registered emulsifiable concentrates on the market that combine pyrimidin, chlorpyrifos, and propargite. This invention innovatively prepares an emulsifiable concentrate by combining pyrimidin, chlorpyrifos, and propargite, which has good weed control effect against resistant grass weeds and has high economic value.

[0007] When using pyrimiflunomide, clopyralid, and propargite EC, poor soil moisture, inadequate drainage, dry weather, low rainfall, or low temperatures after application can all cause phytotoxicity to rice, manifesting as inhibited growth, yellowing leaves, and reduced yield. This invention innovatively adds the safer 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide, which significantly improves the safety of pyrimiflunomide, clopyralid, and propargite EC on rice, thus possessing high economic value. Summary of the Invention

[0008] The purpose of this invention is to provide a highly efficient, environmentally friendly, and safe emulsifiable concentrate of pyrimidine oxime, chloropyridinium chloride, and propargite, as well as their preparation methods and applications.

[0009] 1. To achieve the above objectives, the technical solution adopted by the present invention is as follows: (1) On the one hand, a highly efficient, environmentally friendly, and safe herbicidal compound for controlling weeds in paddy fields is provided, characterized in that it is composed of the following components by weight percentage: 1-3% pyrimidinyl oxime, 1-2% chloropyridinium chloride, 10-30% propargite, 10-25% composite emulsifier, 1-20% co-solvent, 0.05-1% safener, and the balance being solvent. The composite emulsifier is composed of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008; the weight ratio of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 is 1:1-3:2-10; the safener is 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide; and the co-solvent is acetophenone.

[0010] (2) The composite emulsifier is composed of calcium dodecylbenzenesulfonate, Ethylan 324 and Ethylan 1008; the weight ratio of calcium dodecylbenzenesulfonate, Ethylan 324 and Ethylan 1008 is 1:1-3:2-10; (3) Preferably, the highly efficient, environmentally friendly, and safe herbicidal compound for controlling weeds in paddy fields is characterized by comprising the following components by weight percentage: 1.2% pyrimidinyl oxime, 1% chlorofluoropyridine ester, 25.8% propargite, 25% composite emulsifier, 15% cosolvent, 0.5% safener, and the remainder being solvent. The weight ratio of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in the composite emulsifier is 1:2:5.

[0011] (4) The co-solvent is acetophenone, which increases the stability of the pesticide technical in organic solvents and water.

[0012] (5) The safety agent is 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide.

[0013] (6) Preferably, the solvent includes one or more of solvent oil S-150, butyl lactate, cyclohexanone, propylene glycol monomethyl ether, butyl acetate, dimethyl sulfoxide, N-methylpyrrolidone, N,N-dimethylformamide, diethylene glycol butyl ether, solvent oil S-200, ethanol, tetrahydrofurfuryl alcohol, and solvent oil S-100A. Solvent oil S-150 is a preferred solvent.

[0014] (7) On the other hand, the present invention also provides a method for preparing the above-mentioned pyrimidine oxime ether, chloropyridine ester and propargite emulsifiable concentrate, comprising: adding the metered solvent, co-solvent and composite emulsifier into a mixing tank and mixing them evenly; adding pyrimidine oxime ether, chloropyridine ester, propargite and the safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide into the mixing tank and mixing them evenly; turning on the stirring until the materials are completely dissolved and continuing to stir for 30 minutes; stopping the stirring and filtering; and obtaining pyrimidine oxime ether, chloropyridine ester and propargite emulsifiable concentrate after passing the test.

[0015] (9) In another aspect, the present invention also provides the above-mentioned pyrimidine oxime ether, chloropyridine ester and propargite emulsifiable concentrate for the control of grass weeds and to improve the safety of rice.

[0016] (10) Furthermore, the grass weed is barnyardgrass.

[0017] The present invention has the following beneficial effects: 1. This invention optimizes the composition and ratio of the composite emulsifier, and the selected composite emulsifier has good emulsification and wetting effects, and stable emulsion performance.

[0018] 2. The present invention selects a specific co-solvent, and the prepared emulsifiable oil can be automatically dispersed in water and has good stability.

[0019] 3. This invention selects specific safety agents, which greatly improves the safety of the drug compared with drugs without safety agents.

[0020] 4. This invention combines pyrimidine oxime, chlorpyrifos, and propargite into an emulsifiable concentrate, which has a good weed-control effect on resistant grass weeds.

[0021] 5. Compared with using emulsifiers alone, the present invention has a more significant synergistic effect. Detailed Implementation

[0022] The present invention will be further described below with reference to specific embodiments, but the invention is not limited to these specific embodiments. Those skilled in the art should recognize that the present invention covers all alternatives, improvements, and equivalents that may be included within the scope of the claims. 1. Specific Implementation Examples Example 1: 12% Pyrimisulfuron, Clopyralid, and Propanil EC This 12% emulsifiable concentrate of pyrimiflunomide, chloropyridinium chloride, and propargite comprises the following components by weight percentage: pyrimiflunomide 1%, chloropyridinium chloride 1%, propargite 10%, a complex emulsifier 18%, a co-solvent acetophenone 10%, a safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.1%, and solvent oil S-150 to make up the difference. The complex emulsifier is composed of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in a weight ratio of 1:2:7.

[0024] Example 2: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate This 28% emulsifiable concentrate of pyrimiflunomide, chloropyridinium chloride, and propargite comprises the following components by weight percentage: pyrimiflunomide 1.2%, chloropyridinium chloride 1%, propargite 25.8%, a complex emulsifier 25%, a co-solvent acetophenone 15%, a safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up the difference. The complex emulsifier is composed of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in a weight ratio of 1:2:5.

[0025] Example 3: 35% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate This 35% emulsifiable concentrate of pyrimisulfuron, chloropyridinium chloride, and propargite comprises the following components by weight percentage: pyrimisulfuron 3%, chloropyridinium chloride 2%, propargite 30%, a complex emulsifier 20%, a co-solvent acetophenone 20%, a safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 1%, and solvent oil S-150 to make up the difference. The complex emulsifier is composed of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in a weight ratio of 1:3:8.

[0026] To further illustrate the beneficial effects of the present invention, comparative examples are set up using only 28% pyrimimethoxam, chloropyridinium chloride and propargite emulsifiable concentrate from Example 2.

[0027] Comparative Example 1: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate This 28% emulsifiable concentrate of pyrimisulfuron, clopyralid, and propargite comprises the following components by weight percentage: pyrimisulfuron 1.2%, clopyralid 1%, propargite 25.8%, a complex emulsifier 25%, a co-solvent acetophenone 15%, and solvent oil S-150 to make up the difference. The complex emulsifier consists of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in a weight ratio of 1:2:5. No safener was added. Comparative Example 2: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate 28% Pyrimisulfon, chloropyridinium ester, and propargite emulsifiable concentrate, composed of the following components by weight percentage: pyrimisulfon 1.2%, chloropyridinium ester 1%, propargite 25.8%, calcium dodecylbenzenesulfonate 25%, co-solvent acetophenone 15%, safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up. Pure calcium dodecylbenzenesulfonate. Comparative Example 3: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate 28% Pyrimisulfuron, chlorpyrifos, and propargite emulsifiable concentrate, composed of the following components by weight percentage: pyrimisulfuron 1.2%, chlorpyrifos 1%, propargite 25.8%, Ethylan 324 25%, cosolvent acetophenone 15%, safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up. (Plain 324) Comparative Example 4: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate 28% Pyrimisulfuron, chloropyridinium ester, and propargite emulsifiable concentrate, composed of the following components by weight percentage: pyrimisulfuron 1.2%, chloropyridinium ester 1%, propargite 25.8%, Ethylan 1008 25%, cosolvent acetophenone 15%, safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up. (Pure 1008) Comparative Example 5: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate 28% Pyrimisulfon, chloropyridinium ester, and propargite emulsifiable concentrate, composed of the following components by weight percentage: pyrimisulfon 1.2%, chloropyridinium ester 1%, propargite 25.8%, calcium dodecylbenzenesulfonate 10%, Ethylan 324 15%, cosolvent acetophenone 15%, safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up. (Dodecylbenzenesulfonate + 324) Comparative Example 6: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate 28% Pyrimisulfon, chloropyridin, and propargite emulsifiable concentrate, composed of the following components by weight percentage: pyrimisulfon 1.2%, chloropyridin 1%, propargite 25.8%, calcium dodecylbenzenesulfonate 10%, Ethylan 1008 15%, cosolvent acetophenone 15%, safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up. (Dodecylbenzenesulfonate + 1008) Comparative Example 7: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate 28% Pyrimisulfuron, chloropyridinium methyl ester, and propargite emulsifiable concentrate, composed of the following components by weight percentage: pyrimisulfuron 1.2%, chloropyridinium methyl ester 1%, propargite 25.8%, Ethylan 324 10%, Ethylan 1008 15%, co-solvent acetophenone 15%, safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up. 324+1008 Comparative Example 8: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate This 28% emulsifiable concentrate of pyrimisulfuron, chloropyridinium chloride, and propargite comprises the following components by weight percentage: pyrimisulfuron 1.2%, chloropyridinium chloride 1%, propargite 25.8%, compound emulsifier 25%, co-solvent acetophenone 15%, safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up the difference. The compound emulsifier is composed of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in a weight ratio of 2:1:1. The emulsifier ratio is incorrect. Comparative Example 9: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate 28% Pyrimisulfuron, Clopyridyl ester, and Propane EC, composed of the following components by weight percentage: Pyrimisulfuron 1.2%, Clopyridyl ester 1%, Propane 25.8%, co-solvent acetophenone 15%, safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up. No emulsifier added. Comparative Examples 10: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate This 28% emulsifiable concentrate of pyrimisulfuron, chloropyridinium chloride, and propargite comprises the following components by weight percentage: pyrimisulfuron 1.2%, chloropyridinium chloride 1%, propargite 25.8%, a complex emulsifier 25%, a safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up the difference. The complex emulsifier consists of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in a weight ratio of 1:2:5. No co-solvents were added. Comparative Example 11: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate This 28% emulsifiable concentrate of pyrimisulfuron, chloropyridinium ester, and propargite comprises the following components by weight percentage: pyrimisulfuron 1.2%, chloropyridinium ester 1%, propargite 25.8%, a complex emulsifier 25%, a co-solvent cyclohexanone 15%, a safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide 0.5%, and solvent oil S-150 to make up the difference. The complex emulsifier consists of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in a weight ratio of 1:2:5. Other co-solvents were used. Comparative Example 12: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate This 28% emulsifiable concentrate of pyrimisulfuron, chlorpyrifos, and propargite comprises the following components by weight percentage: pyrimisulfuron 1.2%, chlorpyrifos 1%, propargite 25.8%, a complex emulsifier 25%, a co-solvent acetophenone 15%, a safener chlorpyrifos 0.5%, and solvent oil S-150 to make up the difference. The complex emulsifier consists of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in a weight ratio of 1:2:5. Other safeners were used. Comparative Example 13: 28% pyrimimethoxam, clopyralid, and propargite emulsifiable concentrate This 28% emulsifiable concentrate of pyrimisulfuron, clopyralid, and propargite comprises the following components by weight percentage: pyrimisulfuron 1.2%, clopyralid 1%, propargite 25.8%, a complex emulsifier 25%, a co-solvent acetophenone 15%, a safener bis(oxazolyl) acid 0.5%, and solvent oil S-150 to make up the difference. The complex emulsifier consists of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in a weight ratio of 1:2:5. Other safeners were used. 2. Tests of key performance indicators of pyrimidinoxane, clopyralid ester and propargite emulsifiable concentrate The main performance indicators of the emulsifiable concentrates of pyrimimethoxam, chlorpyrifos, and propargite in Examples 1-3 and Comparative Examples 1-13 were determined. The emulsion stability was determined according to GB / T1603-2001 Method for Determination of Emulsion Stability of Pesticides. The cold and hot storage stability were determined according to GB / T19136-2003 Method for Determination of Low Temperature Stability of Pesticides and GB / T19136-2003 Method for Determination of Hot Storage Stability of Pesticides, respectively. Specific data are shown in Table 1.

[0028] Method for testing emulsification and dispersibility: Use a syringe to slowly add 1 mL of emulsifiable oil into a beaker containing hard water from a height of 2 cm above the water surface, and observe the emulsification and dispersibility. Criteria for determining the emulsified dispersion state in water: Level 1: It can disperse quickly, automatically, and evenly, and with slight stirring, it becomes a blue or pale white transparent emulsion; Level 2: It can automatically disperse as a white cloud, and when stirred slightly, it becomes a blue, translucent emulsion; Grade III: Filamentous dispersion, turns into a blue, opaque emulsion after stirring; Grade IV: It sinks as white microspheres and becomes a white, opaque emulsion after stirring; Level 5: It sinks in the form of oil droplets, emulsifies when stirred, and separates into layers when stirring stops.

[0029] Table 1 As can be seen from Table 1, the present invention selects a reasonable component system, and under the synergistic effect of the components, the emulsification effect is good, and all performance indicators are qualified.

[0030] 2. Field efficacy and safety trials Test reagents: pyrimidin oxime, clopyralid, and propargite emulsifiable concentrate from Examples 1-3 and Comparative Examples 1-13; Target pest: Barnyard grass (Echinochloa crus-galli). Safety: Rice. Experimental methods: The experiment was conducted in the field, with each treatment group replicated three times, and the treatment area was approximately 60 m². 2 The rice was applied at the 3-leaf, 1-heart stage, exhibiting good growth, robust plants, and no other pests or diseases. The application method involved using a backpack electric sprayer for even spraying, ensuring no overlap or missed areas. Rice growth was observed 7 days after application, and weed mortality was observed 15 days later. The herbicidal activity of each herbicide was compared. The results are shown in Table 2.

[0031] Table 2 As shown in Table 2, Examples 1-3 of the present invention (all with added safeners) are safe for rice under the same experimental conditions. Comparative Example 1, without the addition of a safener, showed symptoms such as stunting and yellowing of leaves in the rice. Examples 1-3 of the present invention are more effective at controlling barnyardgrass than Comparative Examples 2-13, and have good potential for wider application.

[0032] The above description represents the preferred embodiments of the present invention. It should be noted that those skilled in the art can make various improvements and modifications without departing from the principles of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A herbicidal compound for controlling weeds in rice paddies, characterized in that, Composed of the following components by weight percentage: 1-3% pyrimimethoxam, 1-2% chlorpyrifos, 10-30% propargite, and 10-25% compound emulsifier. The co-solvent comprises 1-20%, the safener 0.05-1%, and the balance being solvent. The composite emulsifier is composed of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008; the weight ratio of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 is 1:1-3:2-10; the safener is 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide; and the co-solvent is acetophenone.

2. The herbicidal compound for controlling weeds in paddy fields according to claim 1, characterized in that, It is composed of the following components by weight percentage: 1.2% pyrimidin, 1% chloropyridinium methyl ether, 25.8% propargite, 25% compound emulsifier, 15% cosolvent, 0.5% safener, and the balance being solvent. The weight ratio of calcium dodecylbenzenesulfonate, Ethylan 324, and Ethylan 1008 in the compound emulsifier is 1:2:

5.

3. The herbicidal compound for controlling weeds in paddy fields according to any one of claims 1-2, characterized in that: The solvents include one or more of the following: solvent oil S-150, butyl lactate, cyclohexanone, propylene glycol monomethyl ether, butyl acetate, dimethyl sulfoxide, N-methylpyrrolidone, N,N-dimethylformamide, diethylene glycol butyl ether, solvent oil S-200, ethanol, tetrahydrofurfuryl alcohol, and solvent oil S-100A.

4. The herbicidal compound for controlling weeds in paddy fields according to claim 3, characterized in that: The solvent is solvent oil S-150.

5. A method for preparing the herbicidal compound for controlling weeds in paddy fields according to any one of claims 1-4, characterized in that, include: After metering, the solvent, co-solvent, and compound emulsifier are added to the mixing tank and mixed evenly. Then, pyrimidine oxime ether, chloropyridine ester, propargite, and the safener 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide are added to the mixing tank and mixed evenly. Stirring is started until the materials are completely dissolved, and stirring is continued for 30 minutes. Stirring is then stopped, the mixture is filtered, and after passing the test, pyrimidine oxime ether, chloropyridine ester, and propargite emulsifiable concentrate are obtained.

6. The application of the herbicidal compound for controlling weeds in paddy fields according to claims 1-4, characterized in that, Used to control annual grass weeds.

7. The application of the herbicidal compound for controlling weeds in paddy fields according to claim 6, characterized in that, The grassy weed in question is barnyardgrass.

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