Topramezone organic salt and application thereof

Abstract

The invention belongs to the field of pesticides, and particularly relates to a topramezone organic salt, a soluble homogeneous liquid herbicide preparation with the topramezone organic salt as an active ingredient and a preparation method of the soluble homogeneous liquid herbicide preparation. The prepared topramezone organic salt, especially the triethanolamine salt, has better dissolving property, and has higher herbicidal activity when being used as a pesticide for preventing and treating field weeds.

Description

Technical Field

[0001] The invention belongs to the field of pesticides, and in particular relates to a benzathine organic salt and a soluble homogeneous liquid herbicide preparation in the form of an active ingredient of the benzathine organic salt and a preparation method thereof. Background Art

[0002] Benzothion, with the chemical name [3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl(]5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone, belongs to the pyrazol herbicide class. By inhibiting 4-hydroxyphenylpyruvate dioxygenase (4-HPPD), the biosynthesis of carotenoids and chlorophyll is inhibited and the function is disturbed, resulting in bleaching symptoms of germinated sensitive weeds within 2-5 days and plant death within 14 days. It has a wide spectrum of weed control and has a control effect on most grass weeds and broad-leaved weeds in corn fields. It can effectively control Setaria, Goosegrass, Chenopodium, Polygonum, Abutilon, Purslane, Xanthium, Solanum nigrum, etc. It can be absorbed by the leaves, roots and stems of weeds and conducted in the plant body, indirectly affecting the synthesis of carotenoids, interfering with the synthesis and function of chloroplasts under light, and ultimately causing severe whitening of the weed heart leaves, tissue necrosis, and weed death. At 20°C, spraying generally takes 2 to 4 days to take effect.

[0003] Due to the physical and chemical properties of benzathine, common product formulation types are suspension concentrates (SC) and oil suspension concentrates (OD), which are heterogeneous formulation systems. This type of formulation has high requirements for the product's pourability, storage stability, and freeze-thaw stability, and therefore often leads to problems such as product agglomeration and poor efficacy. At the same time, benzathine suspension or oil suspension is not easy to make into a premixed product with other soluble herbicides, and incompatibility occurs during tank mixing with other herbicides. In the actual use of common suspension products, additional tank mixing with vegetable oil or mineral oil is usually required to ensure its efficacy in the field, which not only increases the cost of use for farmers, but also brings more environmental risks.

[0004] Patent document CN112601457A discloses an aqueous composition comprising 0.1-1.0 wt% of benzathiazone or its agriculturally acceptable salt based on the total weight of the aqueous composition, wherein the pH of the composition is in the range of 6.5-7.5, and the type of salt is not disclosed. Patent document CN115443990 A discloses a soluble agent containing potassium salt of benzathiazone, wherein the soluble agent comprises 1-30 wt% of potassium salt of benzathiazone expressed as benzathiazone, 40-80 wt% of water, and one or more additives selected from synergists, pigments, preservatives and antifreeze agents. Patent document TW202241878A discloses a crystalline hydrate of sodium salt of benzathiazone, and also provides a method for preparing the crystalline hydrate of sodium salt of benzathiazone and a herbicidal composition comprising the crystalline hydrate of sodium salt of benzathiazone. Patent document US2010075853 A states that the monovalent cation of benzathine is an alkali metal ion selected from Li+, Na+ and K+. It can be seen that the existing documents only disclose the inorganic salt form of benzathine, and no related documents on benzathine organic salt, especially benzathine triethanolamine salt and herbicide composition containing benzathine triethanolamine salt are found. Summary of the invention

[0005] The object of the present invention is to find a benzathine organic salt with good solubility and high herbicidal activity and a herbicidal composition thereof. The benzathine organic salt is benzathine dimethylamine salt, benzathine isopropylamine salt or benzathine triethanolamine salt. Preferably, benzathine triethanolamine salt has the chemical structure:

[0006]

[0007] The preparation method of the triethanolamine salt of fenpyroxene is as follows: adding fenpyroxene technical into water, adding triethanolamine dropwise until the water is completely dissolved while stirring at a speed of 150 to 200 rpm, keeping the water warm at 55 to 65° C. for 2 to 4 hours, then adding disodium EDTA (optional, selected as required), stirring evenly, and cooling the water to room temperature to obtain the triethanolamine salt of fenpyroxene.

[0008] The present invention provides a composition comprising a benzathine organic salt, preferably a homogeneous and stable herbicidal active liquid formulation containing a) a benzathine organic salt and a solvent b). The herbicidal active ingredient may comprise a) alone or may comprise one or more other herbicidal active ingredients d).

[0009] The mass concentration of a) in the composition of the present invention is 0.1%-50%.

[0010] b) in the composition of the present invention can be selected from: water, N-methylpyrrolidone, N,N-dimethylformamide, dimethyl sulfoxide, amides (C 6 -C 10), diethylene glycol, cyclohexanone, isobutanol, cyclohexanone, isophorone, or a combination of two or more thereof.

[0011] The mass ratio of a) to b) in the composition of the present invention is 1:1 to 1:1000.

[0012] The composition of the present invention may further comprise one or more auxiliary agents c), including: antifreeze agents c1), surfactants c2), pH regulators c3), and defoaming agents c4).

[0013] The component c1) of the present invention may be selected from: glycerol, ethylene glycol, propylene glycol, or a combination of two or more thereof.

[0014] The component c2) of the present invention can be selected from: alkyl glycosides, fatty alcohol polyoxyethylene ether (AEO), styrylphenol polyoxyethylene ether, EO / PO block polyether, coconut oil alkylamine ethoxylate, tridecyl alcohol polyether, fatty alcohol polyoxyethylene ether sulfate (AES), sodium fatty acid methyl ester sulfonate (MES), cocamidopropyl dimethylamine and one or more combinations thereof.

[0015] The component c3) of the present invention can be selected from: one or more combinations of EDTA, citric acid, triethanolamine, triethylamine, dimethylamine, and isopropylamine.

[0016] The component c4) of the present invention may be selected from: polysiloxanes, polyether-modified silicone defoamers, or a combination of two thereof.

[0017] The mass ratio of a) and c) in the composition of the present invention is 1:0.001 to 1:1000.

[0018] The composition of the present invention may further comprise one or more other herbicides d), which may be selected from hexazinone, thidiazuron, sulfamethoxam, bromoxynil, acetochlor, isopropyl metolachlor, S-isopropyl metolachlor, glyphosate, glufosinate, S-gluten, clopyralid, bentazone, imazapyr, trifluorfen, diquat, paraquat, amiloride, dicamba, 2,4-D, 2,4-DP, 2,4-DP-p, 2,4-DB, MCPA, MCPB, fomesafen, imazapyr, methoxyfen, triclopyralid, imazapyr, imazapyr, quinolinic acid, bispyribac-butyl, fluazifop-butyl, aminopyralid, and the like.

[0019] The mass ratio of a) and d) in the composition of the present invention is 1:0.01 to 1:200.

[0020] The composition of the present invention can be used by spraying before sowing, before germination or after germination on a variety of crops and non-agricultural crops that are tolerant to herbicides through traditional breeding or genetic engineering, such as coffee, palm, rubber, citrus, apple, banana, peanut, rapeseed, corn, soybean, sorghum, sugarcane, sunflower, cotton, rice, wheat, barley, millet, oats, rye, etc.

[0021] Compared with the prior art, the present invention has the following beneficial effects:

[0022] 1) It has better biological activity than its suspension and inorganic salt forms; 2) The composition has better storage stability than its suspension and does not form precipitates; 3) It is more conducive to uniform dilution, homogeneous dissolution or dispersion in water than the suspension, suitable for large-scale spray equipment, and does not block the nozzle; 4) It can be made into a homogeneous premixed liquid preparation with other herbicides and has better adaptability. DETAILED DESCRIPTION

[0023] The present invention is further explained below in conjunction with specific implementation modes.

[0024] Example 1: Solubility test of fenthion salt

[0025] Test method:

[0026] The solubility test method of various salts of fenpyroxene at room temperature (18.5°C) is as follows: 10.2 g of 98% fenpyroxene is weighed into a sealed container, a certain mass of alkali is added at a 1:1 molar ratio, 20 g of water is added, stirring is started until the mixture returns to room temperature, water is slowly added until fenpyroxene is completely dissolved, and the solubility of fenpyroxene is calculated.

[0027]

[0028] Test steps:

[0029] Potassium salt of fenpyroxetine: In a sealed container, add 10.2g of 98% fenpyroxetine and 1.81g of 85% potassium hydroxide, add water to 20g, start stirring until the mixture returns to room temperature, and continue to slowly add water until fenpyroxetine is completely dissolved. The total weight is 43.5g, and the solubility of fenpyroxetine is 23.0%.

[0030] Tomezopyralid sodium salt: In a sealed container, add 10.2g of 98% tomezopyralid and 1.25g of 96% sodium hydroxide, add water to 20g, start stirring until the mixture returns to room temperature, and continue to slowly add water until tomezopyralid is completely dissolved. The total weight is 48.1g, and the solubility of tomezopyralid is 20.8%.

[0031] Benzophenone ammonium salt: In a sealed container, add 10.2g of 98% benzathine and 2.34g of 20% ammonia water, add water to 20g, start stirring until the mixture returns to room temperature, and continue to slowly add water until the benzathine is completely dissolved. The total weight is 90.1g, and the solubility of benzathine is 11.1%.

[0032] Benzophenone dimethylamine salt: In a sealed container, add 10.2g of 98% benzathine and 3.10g of 40% dimethylamine, add water to 20g, start stirring until the mixture returns to room temperature, and continue to slowly add water until the benzathine is completely dissolved. The total weight is 40g, and the solubility of benzathine is 25.0%.

[0033] Benzophenone isopropylamine salt: In a sealed container, add 10.2g of 98% benzathine and 2.37g of 70% isopropylamine, add water to 20g, start stirring until the mixture returns to room temperature, and continue to slowly add water until the benzathine is completely dissolved. The total weight is 37g, and the solubility of benzathine is 27.0%.

[0034] Benzophenone triethanolamine salt: In a sealed container, add 10.2g of 98% benzathone and 4.08g of 99% triethanolamine, add water to 20g, start stirring until the mixture returns to room temperature, and continue to slowly add water until the benzathone is completely dissolved. The total weight is 25g, and the solubility of benzathone is 40.0%.

[0035] Test results: As shown in Table 1, the solubility of fenpyrazone can be significantly increased to 40% by preparing fenpyrazone in the form of an organic salt, especially in the form of fenpyrazone triethanolamine salt, with fenpyrazone inorganic salts (sodium salt, potassium salt, ammonium salt).

[0036] Table 1: Solubility data table

[0037]

[0038] Example 2: Field efficacy test report of different soluble solutions of benzathine salts on weeds in corn fields

[0039] Purpose of the experiment: To test and compare the control effect of different forms of benzathine salts on the main weeds in corn fields and their safety to corn through field experiments;

[0040] Test crops: Xianyu 335;

[0041] Weed types: annual grass weeds and broadleaf weeds;

[0042] Cultivation conditions: The experiment was conducted at Qixingpao Farm in Nenjiang City. The soil in the experimental site was black soil with medium texture, 3.62% organic matter content and pH value of 6.79. The previous crop was corn, which was plowed and harrowed in autumn and ridged in spring with a ridge spacing of 65 cm.

[0043] Test agents: 10% benzathone sodium salt soluble agent, 10% benzathone potassium salt soluble agent, 10% benzathone ammonium salt soluble agent, 10% benzathone isopropylamine salt soluble agent, 10% benzathone triethanolamine salt soluble agent, 10% benzathone sodium salt soluble agent, 10% benzathone dimethylamine salt soluble agent, manufacturer: Nantong Taihe Chemical Co., Ltd.;

[0044] Control agent: 30% fenpyroxil suspension, commercially available;

[0045] Table 2: Dosages and treatment numbers:

[0046]

[0047] Plot arrangement: The experiment had 8 treatments, 4 replications, 32 plots, and each plot had an area of ​​25 m2. The first replication was arranged in sequence, and the other three replications were arranged in random blocks.

[0048] Application method: Apply pesticide once after corn seedlings on June 8. Corn is at 3.5-5 leaf stage, weeds are at 2-4 leaf stage, use a backpack compression sprayer for plots, spray width 2m, 4 flat fan nozzles, working pressure 4kg / cm2, spray volume 250L / hectare.

[0049] Investigation method: Observe crop safety after application of pesticides, and investigate weed control efficacy on fresh weight 28 days after application.

[0050] Test results:

[0051] As shown in Table 3, the organic salt of fenpyroxene has better biological activity than its fenpyroxene suspension concentrate and fenpyroxene inorganic salt; in particular, the triethanolamine salt of fenpyroxene has the best control effect on annual grass weeds and broad-leaved weeds in corn fields.

[0052] Crop safety: 3-5 days, 14 days, and 28 days after application, no obvious symptoms of corn damage were found in any of the treatment areas. The corn grew normally throughout the entire growth period, and there was no difference in corn growth between the sprayed area and the manual weeding area.

[0053] Table 3: Field efficacy of different soluble solutions of fenthion salts against weeds in corn fields

[0054]

[0055] Example 3: Preparation of fenpyrazone triethanolamine salt

[0056] According to the following method: add the benzothiazone technical into water, add triethanolamine dropwise while stirring at a speed of 150 to 200 rpm until it is completely dissolved, keep warm at 55 to 65°C for 2 to 4 hours, then add disodium EDTA (optional), stir evenly, and cool to room temperature to obtain benzothiazone triethanolamine salt.

[0057] Example 4: Preparation of 20% benzothiocarb triethanolamine soluble solution

[0058] According to the following formula: 20% benzathine triethanolamine salt, 8% alkyl glycoside (C10-C12), 5% fatty alcohol polyoxyethylene ether, 0.1% SAG-1572 defoamer, 0.1% tartrazine, and deionized water to 100%, a 20% benzathine triethanolamine salt soluble solution was prepared using a conventional soluble solution preparation method. After sampling, the general indicators of soluble solutions were analyzed based on NY / T2989-2016. The results are as follows:

[0059]

[0060]

[0061] Example 5: Preparation of 10.5% benzathine triethanolamine·glufosinate ammonium soluble solution

[0062] According to the following formula: 0.5% benzathine triethanolamine salt, 10% glufosinate ammonium salt, 4% propylene glycol methyl ether, 15% sodium sulfate of fatty alcohol polyoxyethylene ether, 0.07% ZY-8262 (organic silicone defoamer), 0.1% 1% brilliant blue aqueous solution, deionized water is added to 100%, and a 15.5% benzathine triethanolamine·glyphosate triethanolamine soluble solution is prepared using a conventional preparation method. After sampling, the general indicators of soluble solutions are analyzed based on NY / T2989-2016. The results are as follows:

[0063]

[0064] Example 6: Preparation of 11.4% fenpyrazone triethanolamine salt·2,4-D microemulsion

[0065] According to the following formula: containing 1.4% benzathine triethanolamine salt, 10% 2,4-D, 2% N-methylpyrrolidone, 4% cyclohexane, 8% amides (C6-C10), 12% arylphenol polyoxyethylene ether, 4% EO / PO block polyether, and deionized water to 100%, a 11.4% benzathine triethanolamine·2,4-D microemulsion was prepared using a conventional formulation method. After sampling, the general indicators of microemulsions were analyzed based on NY / T2989-2016. The results are as follows:

[0066]

[0067] Finally, it should be noted that the above embodiments are only used to illustrate the technical solution of the present invention, rather than to limit it.

Claims

1. A fenpyroxidine organic salt, characterized in that: The benzathone organic salt is benzathone dimethylamine salt, benzathone isopropylamine salt or benzathone triethanolamine salt.

2. The organic salt of fenpyroxetine according to claim 1, characterized in that The organic salt of fenpyroxene is fenpyroxene triethanolamine salt, and its chemical structure is:

3. A herbicidally active composition, characterized in that: The method comprises the benzathine organic salt according to claim 1 or 2 and one or more other herbicides.

4. The composition according to claim 3, characterized in that The mass ratio of the organic salt of fenpyrox to other herbicides is 1:0.01 to 1:

200.

5. The composition according to claim 3, characterized in that The other herbicides are selected from hexazinone, thidiazuron, sulfamethoxam, bromoxynil, acetochlor, isopropyl metolachlor, S-isopropyl metolachlor, glyphosate, glufosinate, S-gluten, clopyralid, bentazone, imazapyr, trifluorfen, diquat, paraquat, amiloride, dicamba, 2,4-D, MCPA, MCPB, fomesafen, imazapyr, methazapyr, triclopyrazone, imazapyr, imazapyr, quinolinic acid, bispyribac-butyl, fluazifop-butyl or clomipyralid.

6. The composition according to claim 3, characterized in that It also contains auxiliary ingredients of pesticides.

7. The composition according to claim 5, characterized in that The mass concentration of the benomyl organic salt is 0.1%-50%.

8. The composition according to claim 6, characterized in that The composition is prepared in the form of a soluble liquid or microemulsion.

9. Use of the benzathine organic salt according to claim 1 or 2 or the composition according to any one of claims 3 to 8 for controlling crop weeds.

10. The use according to claim 9, characterized in that The corn is used as corn and the weeds are annual grass weeds and / or broadleaf weeds.

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