CN119977955A - A kind of benzathine organic salt and its application - Google Patents
A kind of benzathine organic salt and its application Download PDFInfo
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- CN119977955A CN119977955A CN202510136103.9A CN202510136103A CN119977955A CN 119977955 A CN119977955 A CN 119977955A CN 202510136103 A CN202510136103 A CN 202510136103A CN 119977955 A CN119977955 A CN 119977955A
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- topramezone
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Abstract
The invention belongs to the field of pesticides, and in particular relates to topramezone organic salt and a soluble homogeneous phase liquid herbicide preparation taking topramezone organic salt as an active ingredient and a preparation method thereof. The topramezone organic salt, especially the triethanolamine salt, prepared by the invention has better solubility and higher weeding activity when being used as a field weed control medicament.
Description
Technical Field
The invention belongs to the field of pesticides, and in particular relates to topramezone organic salt and a soluble homogeneous phase liquid herbicide preparation taking topramezone organic salt as an active ingredient and a preparation method thereof.
Background
Topramezone, the chemical name of which is [3- (4, 5-dihydro-3-isoxazolyl) -2-methyl-4- (methylsulfonyl) phenyl (] 5-hydroxy-1-methyl-1H-pyrazol-4-yl) methanone, belongs to pyrazole (Pyrazo l es) herbicides. By inhibiting 4-hydroxyphenylpyruvate dioxygenase (4-HPPD), biosynthesis of carotenoid and chlorophyll is inhibited and functions are disturbed, so that sprouted sensitive weeds are bleached within 2-5 days, the death of plants within 14 days has a broad weed killing spectrum, and the plant-killing agent has a control effect on most gramineous weeds and broadleaf weeds in corn fields, and can effectively control green bristlegrass, gooseberry, chenopodium quinoa, polygonum, abutilon, purslane, siberian cocklebur, black nightshade and the like. Can be absorbed by leaves, roots and stems of weeds and is transmitted in plants, so that the synthesis of carotenoid is indirectly influenced, the synthesis and the function of chloroplasts are interfered under illumination, and the serious whitening of heart leaves, tissue necrosis and death of weeds are finally caused. Can take effect after spraying medicine for 2-4 days at 20 ℃.
Because of the physicochemical properties of topramezone, the common product preparation types are suspending agents (SC) and oil suspending agents (OD), and are heterogeneous preparation systems, the preparation types have higher requirements on the pourability, storage stability and freeze thawing stability of the product, and therefore, the problems of product caking, poor drug effect performance and the like often occur. Meanwhile, the topramezone suspending agent or the oil suspending agent and other soluble herbicides are not easy to prepare into a premixed product, and are incompatible in the barrel mixing use process of the other herbicides. In the actual use process of common suspending agent products, additional barrels of vegetable oil or mineral oil are usually required to ensure the field efficacy performance of the suspending agent products, so that the use cost of farmers is increased, and more environmental risks are brought.
Patent document CN112601457a discloses an aqueous composition comprising 0.1-1.0 wt% topramezone or an agriculturally acceptable salt thereof based on the total weight of the aqueous composition, wherein the pH of the composition is in the range of 6.5-7.5, which does not disclose the kind of salt. Patent document CN115443990 a discloses a soluble agent containing topramezone potassium salt, which comprises 1-30 wt% topramezone potassium salt expressed as topramezone, 40-80 wt% moisture, and one or more additive auxiliaries selected from synergists, pigments, preservatives and antifreezes. Patent document TW202241878a discloses a crystalline hydrate of topramezone sodium salt, and also provides a method for preparing the crystalline hydrate of topramezone sodium salt and a herbicidal composition comprising the crystalline hydrate of topramezone sodium salt. The monovalent cation of topramezone of patent document US2010075853 a is an alkali metal ion selected from li+, na+ and k+. The prior literature only discloses the form of the topramezone inorganic salt, and the topramezone organic salt, in particular the topramezone triethanolamine salt and the herbicide composition containing the topramezone triethanolamine salt are not described in the related literature.
Disclosure of Invention
The invention aims to find a topramezone organic salt with better solubility and higher herbicidal activity and a herbicidal composition thereof. Is benzole (benzene azole) oxadiazon is topramezone dimethylamine salt topramezone isopropyl amine salt or topramezone triethanolamine salt. The preferred is topramezone triethanolamine salt, which has the chemical structure:
The preparation method of the topramezone triethanolamine salt comprises the steps of adding topramezone raw material into water, dropwise adding triethanolamine to be completely dissolved when stirring at the speed of 150-200 r/min, preserving heat for 2-4 hours at the temperature of 55-65 ℃, then adding EDTA disodium (optional according to the requirement), stirring uniformly, and cooling to room temperature to obtain the topramezone triethanolamine salt.
The invention provides a composition comprising topramezone organic salt, preferably a homogeneous stable herbicidal active liquid formulation comprising topramezone organic salt a) and solvent b), the herbicidal active ingredient may comprise a) alone or one or more other herbicidal active ingredients d).
The mass concentration of a) in the composition is 0.1% -50%.
The b) in the composition can be selected from one or more than two of water, N-methyl pyrrolidone, N-dimethylformamide, dimethyl sulfoxide, amides (C 6-C10), diethylene glycol, cyclohexanone, isobutanol, cyclohexanone and isophorone.
A) and b) in the composition according to the invention in a mass ratio of 1:1 to 1:1000.
The composition according to the invention may also comprise one or more auxiliary agents c), including antifreeze agents c 1), surfactants c 2), pH regulators c 3), defoamers c 4).
The component c 1) of the invention can be one or more than two of glycerol, ethylene glycol and propylene glycol.
The component c 2) of the invention can be selected from one or more of alkyl glycoside, fatty alcohol polyoxyethylene ether (AEO), styrylphenol polyoxyethylene ether, EO/PO block polyether, cocoalkylamine ethoxycompound, tridecyl alcohol polyether, fatty alcohol polyoxyethylene ether sulfate (AES), fatty acid methyl sodium sulfonate (MES) and cocoamidopropyl dimethylamine.
Component c 3) of the invention can be one or a combination of more than one of EDTA, citric acid, triethanolamine, triethylamine, dimethylamine and isopropylamine.
The component c 4) of the invention can be one or the combination of two of polysiloxane and polyether modified organosilicon defoamer.
A) and c) in the composition according to the invention, the mass ratio of the two is 1:0.001 to 1:1000.
The composition according to the invention may further comprise one or more further herbicides D) which may be selected from the group consisting of hexazinone, thidiazuron, sulfentrazone, bromoxynil, acetochlor, metolachlor, mefenacet, glyphosate, glufosinate-ammonium, clopyralid, bentazone, imazethapyr, acifluorfen, diquat, paraquat, picloram, dicamba, 2,4-D, 2,4-DP-p, 2,4-DB, MCPA, MCPB, fomesafen, imazethapyr, triclopyr, imazethapyr, imidazoquin, bispyribac, fluoroethyl, aminopyralid and the like.
A) and d) in the composition according to the invention in a mass ratio of 1:0.01 to 1:200.
The composition of the invention can be applied to various crops and non-crops which are tolerant to herbicide after traditional breeding or genetic engineering modification by a pre-sowing, pre-emergence or post-emergence spraying mode, such as coffee, palm, rubber, citrus, apple, banana, peanut, rape, corn, soybean, sorghum, sugarcane, sunflower, cotton, rice, wheat, barley, millet, oat, rye and the like.
Compared with the prior art, the invention has the beneficial effects that:
1) better biological activity than the suspending agent and inorganic salt existing form, 2) better storage stability than the suspending agent, no precipitate formation, 3) better uniform dilution, uniform dissolution or dispersion in water than the suspending agent, suitability for large-scale spraying equipment and no nozzle blockage, 4) better suitability for preparing homogeneous premix liquid preparation with other herbicides.
Detailed Description
The invention is further illustrated with reference to specific embodiments.
Example 1 topramezone salt solubility test
The test method comprises the following steps:
The method for testing the solubility of various salts of topramezone at room temperature (18.5 ℃) comprises the steps of weighing 10.2g of 98% topramezone in a closed container, adding a certain mass of alkali according to a molar ratio of 1:1, adding 20g of water, starting stirring until the mixed solution returns to the room temperature, continuously and slowly adding water until the topramezone is completely dissolved, and calculating the solubility of the topramezone.
The test steps are as follows:
The topramezone potassium salt is that 10.2g of 98% topramezone and 1.81g of 85% potassium hydroxide are added into a closed container, water is added to 20g, stirring is started until the mixed solution returns to room temperature, water is continuously and slowly added until the topramezone is completely dissolved, the total weight is 43.5g, and the topramezone solubility is 23.0%.
The topramezone sodium salt is prepared by adding 10.2g of 98% topramezone and 1.25g of 96% sodium hydroxide into a closed container, supplementing water to 20g, starting stirring until the mixed solution returns to room temperature, and continuously and slowly supplementing water until the topramezone is completely dissolved, wherein the total weight is 48.1g, and the topramezone solubility is 20.8%.
The topramezone ammonium salt is prepared by adding 10.2g of 98% topramezone and 2.34g of 20% ammonia water into a closed container, supplementing water to 20g, starting stirring until the mixed solution returns to room temperature, and continuously and slowly supplementing water until the topramezone is completely dissolved, wherein the total weight is 90.1g and the topramezone solubility is 11.1%.
The carfentrazone-ethyl dimethylamine salt is prepared by adding 10.2g of 98% carfentrazone-ethyl and 3.10g of 40% dimethylamine into a closed container, supplementing water to 20g, starting stirring until the mixed solution returns to room temperature, and continuously and slowly supplementing water until the carfentrazone-ethyl is completely dissolved, wherein the total weight is 40g, and the solubility of the carfentrazone-ethyl is 25.0%.
The topramezone isopropyl amine salt is prepared by adding 10.2g of 98% topramezone and 2.37g of 70% isopropyl amine into a closed container, supplementing water to 20g, starting stirring until the mixed solution returns to room temperature, and continuously and slowly supplementing water until the topramezone is completely dissolved, wherein the total weight is 37g, and the topramezone solubility is 27.0%.
The carfentrazone-ethyl triethanolamine salt is prepared by adding 10.2g of 98% carfentrazone-ethyl and 4.08g of 99% triethanolamine into a closed container, supplementing water to 20g, starting stirring until the mixed solution returns to room temperature, and continuously and slowly supplementing water until the carfentrazone-ethyl is completely dissolved, wherein the total weight is 25g, and the solubility of the carfentrazone-ethyl is 40.0%.
Test results show that the solubility of the topramezone can be obviously improved to 40% by preparing the topramezone into an organic salt form, particularly into a topramezone triethanolamine salt form with the topramezone inorganic salt (sodium salt, potassium salt and ammonium salt) as shown in table 1.
TABLE 1 solubility data sheet
Example 2 field efficacy test report of different topramezone salt soluble Agents on corn field weeds
The test aims are to test and compare the prevention effect of different topramezone salt existence forms on main weeds in a corn field and the safety of corn through field test;
test crop, first jade 335;
weed species, annual grassy weeds and broadleaf weeds;
Cultivation conditions the test was performed on a seven-star bubble farm in the city of tender river. The soil of the test land is black soil, has medium texture, 3.62 percent of organic matter and 6.79 of pH value. Corn of previous crop, turning over in autumn, harrowing in autumn, ridging in spring, and ridge distance of 65cm;
The test reagent comprises 10% of topramezone sodium salt soluble agent, 10% of topramezone potassium salt soluble agent, 10% of topramezone ammonium salt soluble agent, 10% of topramezone isopropyl amine salt soluble agent, 10% of topramezone triethanolamine salt soluble agent, 10% of topramezone sodium salt soluble agent and 10% of topramezone dimethylamine salt soluble agent, and the manufacturers are Nannong He chemical company;
the control medicament is 30% topramezone suspending agent which is sold in the market;
table 2 dosage and treatment number:
cell arrangement test total 8 treatments, 4 replicates, 32 cells, 25m2 per cell area. The I-th repetition is arranged in sequence, and the other three repetitions are arranged in random granules.
The application method comprises 1 time of application after corn seedling, and the application time is 6 months and 8 days. The corn is applied in 3.5-5 leaf stage and weed is applied in 2-4 leaf stage, the application adopts a special knapsack compression sprayer for the district, 2m of spraying width, 4 flat fan-shaped nozzles and the working pressure is 4kg/cm < 2 >. The spray rate was 250 liters/hectare.
The investigation method is to observe the safety of crops after the application and investigate the fresh weight control effect of weeds for 28 days after the application.
Test results:
As shown in Table 3, the topramezone organic salt has better biological activity than the topramezone suspending agent and the topramezone inorganic salt, and especially the topramezone triethanolamine salt has the best control effect on annual gramineous weeds and broadleaf weeds in corn fields.
The crop safety is that the corn has no obvious phytotoxicity symptoms in each treatment area at 3-5 days, 14 days and 28 days after the application, the whole growth period is normal, and the application area has no difference with the corn growth in the artificial weeding area.
TABLE 3 field efficacy of different topramezone salt soluble agents against corn field weeds
Example 3 preparation of topramezone triethanolamine salt
The method comprises the steps of adding topramezone raw material into water, dropwise adding triethanolamine to be completely dissolved when stirring at the speed of 150-200 r/min, preserving heat for 2-4 hours at the temperature of 55-65 ℃, then adding EDTA disodium (optional), stirring uniformly, and cooling to room temperature to obtain the topramezone triethanolamine salt.
EXAMPLE 4 preparation of 20% topramezone triethanolamine salt soluble solution
The preparation method comprises the following steps of preparing 20% of topramezone triethanolamine salt, 8% of alkyl glycoside (C10-C12), 5% of fatty alcohol polyoxyethylene ether, 0.1% of SAG-1572 defoamer, 0.1% of lemon yellow and 100% of deionized water, preparing the solution into 20% of topramezone triethanolamine salt by using a conventional preparation method of the solution, and analyzing the general index of the solution based on NY/T2989-2016 after sampling, wherein the results are as follows:
EXAMPLE 5 preparation of 10.5% topramezone triethanolamine-arginate-ammonium salt soluble solution
The preparation method comprises the following steps of preparing a topramezone triethanolamine salt 0.5%, a refined glufosinate ammonium salt 10%, propylene glycol methyl ether 4%, fatty alcohol polyoxyethylene ether sodium sulfate 15%, ZY-8262 (organic silicon defoamer) 0.07%, a 1% brilliant blue aqueous solution 0.1%, and deionized water to 100%, preparing a 15.5% topramezone triethanolamine-glyphosate triethanolamine salt soluble agent by using a conventional preparation method, analyzing general indexes of the soluble agent based on NY/T2989-2016 after sampling, and obtaining the following results:
EXAMPLE 6 preparation of 11.4% topramezone triethanolamine salt 2,4-D microemulsion
The preparation method comprises the following steps of preparing 11.4% of topramezone triethanolamine, 2, 4-D10%, N-methylpyrrolidone 2%, cyclohexane 4%, amide (C6-C10) 8%, aryl phenol polyoxyethylene ether 12%, EO/PO block polyether 4%, and deionized water to 100%, preparing into 11.4% of topramezone triethanolamine, 2,4-D microemulsion by using a conventional preparation method, and analyzing general indexes of the microemulsion based on NY/T2989-2016 after sampling, wherein the results are as follows:
finally, it should be noted that the above embodiments are only for illustrating the technical solution of the present invention, and are not limiting.
Claims (10)
1. An organic salt of topramezone, which is characterized in that, the topramezone organic salt is topramezone dimethylamine salt topramezone isopropyl amine salt or topramezone triethanolamine salt.
2. The topramezone organic salt according to claim 1, which is topramezone triethanolamine salt and has the chemical structure:
3. A herbicidally active composition comprising an organic salt of topramezone according to claim 1 or 2 and one or more other herbicides.
4. A composition according to claim 3, characterized in that the mass ratio of topramezone organic salt to other herbicide is 1:0.01 to 1:200.
5. The composition according to claim 3, wherein, the other herbicide is selected from hexazinone, thidiazuron, sulbenazolin, bromoxynil, acetochlor, metolachlor, chlor-sodium, chlor-glyphosate, glufosinate, clopyralid, bentazone, imazethapyr, acibenzolar-s-methyl, and the like glyphosate, glufosinate, arginate, clopyralid bentazone, imazethapyr, acibenzolar-s-methyl.
6. A composition according to claim 3, further comprising a pesticidal adjuvant ingredient.
7. The composition according to claim 5, wherein the mass concentration of the topramezone organic salt is 0.1% -50%.
8. The composition of claim 6, wherein the formulation of the composition is a soluble liquid or microemulsion.
9. Use of an organic salt of topramezone according to claim 1 or 2 or of a composition according to any one of claims 3 to 8 for controlling crop weeds.
10. The method according to claim 9, wherein the corn is annual grassy weeds and/or broadleaf weeds.
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| CN111362912A (en) * | 2018-12-25 | 2020-07-03 | 青岛清原化合物有限公司 | Cyclopyraflutole triethanolamine salt and preparation method and application thereof |
| CN112601457A (en) * | 2018-08-27 | 2021-04-02 | 巴斯夫欧洲公司 | Aqueous compositions of topramezone |
| CN112839513A (en) * | 2018-10-03 | 2021-05-25 | 巴斯夫欧洲公司 | Oxaflutole microemulsion composition |
| EP4008185A1 (en) * | 2020-12-03 | 2022-06-08 | BASF Agro B.V. | Herbicidal composition comprising a saflufenacil microparticles |
| TW202241878A (en) * | 2021-02-12 | 2022-11-01 | 香港商龍燈農業化工國際有限公司 | Novel crystalline hydrate of topramezone sodium salt and preparation method therefor |
| CN115443990A (en) * | 2022-08-31 | 2022-12-09 | 济南绿霸农药有限公司 | Soluble solution containing topramezone potassium salt and preparation method thereof |
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2025
- 2025-02-07 CN CN202510136103.9A patent/CN119977955A/en active Pending
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1248255A (en) * | 1997-01-17 | 2000-03-22 | 巴斯福股份公司 | 3-heterocyclyl-substituted benzoyl derivatives |
| US20100075853A1 (en) * | 2006-11-27 | 2010-03-25 | Basf Se | Herbicidally active composition containing a monovalent salt of 4-[2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-methyl-5-hydroxy-1h-pyrazole |
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| CN111362912A (en) * | 2018-12-25 | 2020-07-03 | 青岛清原化合物有限公司 | Cyclopyraflutole triethanolamine salt and preparation method and application thereof |
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| TW202241878A (en) * | 2021-02-12 | 2022-11-01 | 香港商龍燈農業化工國際有限公司 | Novel crystalline hydrate of topramezone sodium salt and preparation method therefor |
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