A pyroxasulfone microemulsion and a preparation method and application thereof

Abstract

This invention relates to the field of pesticide microemulsion technology, specifically to a pyrimethanil microemulsion, its preparation method, and its application. The pyrimethanil microemulsion, by mass percentage, comprises 5-15% pyrimethanil, 10-25% organic solvent, 5-10% co-solvent, 15-30% adjuvant, and water as the balance; the organic solvent comprises a composition formed by 150# solvent oil and N,N-dimethyloctyldecanoate or cyclohexanone. The pyrimethanil microemulsion provided in this application maintains a transparent storage state, exhibits higher stability, is beneficial for the expression of pyrimethanil efficacy, improves weed control effect, and is easier for farmers to use.

Description

Technical Field

[0001] This invention relates to the field of pesticide microemulsion technology, specifically to a pyrimethanil microemulsion, its preparation method, and its application. Background Technology

[0002] Benzimidazole is a non-selective herbicide and also belongs to the PPO inhibitor category. Benzimidazole has excellent weed control performance, filling the gap in the control of glyphosate and glufosinate-resistant weeds. However, the mechanism of action of benzimidazole is different from that of mainstream herbicides, and weeds develop resistance to it more slowly. This gives benzimidazole a significant advantage in controlling resistant weeds. Benzimidazole is characterized by low toxicity, low residue, high efficiency, rapid effect, and wide application range.

[0003] Chinese invention patent application CN105613572A discloses a microemulsion containing glufosinate and its preparation method. The active ingredient A is glufosinate, and the active ingredient B is selected from ethoxyflufenoxam, ethoxyflufenoxam, or clethodim. The weight percentages of each component are: active ingredient A 14%-25%, active ingredient B 0.5%-3%, solvent 2%-5%, cosolvent 5%-20%, surfactant 8%-20%, synergistic stabilizer 5%-10%, and the balance being water. The application addresses the issue of the coexistence stability of the active ingredients in the raw material system. However, it does not address the problems of gelation, paste formation, and non-flowability that may occur during the microemulsion formulation process, nor does it address the issue of incomplete dissolution of the active ingredient pyrimethanil, which could lead to failure in the microemulsion formulation process.

[0004] Therefore, providing a pyrimethanil microemulsion with good solubility, storage stability, and dilution stability is the main technical problem that needs to be solved. Summary of the Invention

[0005] To address the aforementioned technical problems, the first aspect of this invention provides a pyrimethanil microemulsion, the raw materials for which, by mass percentage, are: 5-15% pyrimethanil, 10-25% organic solvent, 5-10% co-solvent, 15-30% auxiliaries, and the balance being water; wherein the organic solvent comprises a composition formed by 150# solvent oil and N,N-dimethyloctadecanamide or cyclohexanone.

[0006] To improve the expression of pyrimethanil efficacy in pyrimethanil microemulsions, the inventors discovered during experiments that using a combination of pyrimethanil, organic solvents, co-solvents, adjuvants, and water, specifically a combination of 150# solvent oil and N,N-dimethyloctadecanamide or cyclohexanone as the organic solvent, allows the pyrimethanil microemulsion to remain transparent, thus enhancing the expression of pyrimethanil efficacy. This is likely because the combination of 150# solvent oil and N,N-dimethyloctadecanamide or cyclohexanone as an organic solvent increases the solubility of pyrimethanil and maintains the transparency of the pyrimethanil microemulsion during storage and dilution. This further improves the expression of pyrimethanil in practical applications, reduces the amount of pyrimethanil microemulsion used, and enhances the weeding effect.

[0007] In one embodiment, the organic solvent comprises 150# solvent oil and N,N-dimethyloctyldecylamide, wherein the mass ratio of N,N-dimethyloctyldecylamide to pyrimethanil is (1-2):1.

[0008] In one embodiment, the organic solvent is composed of 150# solvent oil and N,N-dimethyloctyldecamide; the mass ratio of the 150# solvent oil to N,N-dimethyloctyldecamide is 1:(1-3).

[0009] In one embodiment, the organic solvent is composed of 150# solvent oil and cyclohexanone; the mass ratio of the 150# solvent oil to cyclohexanone is 1:(1-3).

[0010] To improve the solubility of pyrimethanil and obtain a clear and transparent pyrimethanil microemulsion, avoiding the problem of opacity under cold storage conditions, the inventors discovered during experiments that when the organic solvent used is composed of 150# solvent oil and N,N-dimethyloctyldecylamide or 150# solvent oil and cyclohexanone, the mass ratio of 150# solvent oil to N,N-dimethyloctyldecylamide is 1:(1-3) or the mass ratio of 150# solvent oil to cyclohexanone is 1:(1-3), and the mass ratio of N,N-dimethyloctyldecylamide to pyrimethanil is (1-2):1, the solubility of pyrimethanil can be improved, the stability of the pyrimethanil microemulsion can be improved, and a clear and transparent pyrimethanil microemulsion can be obtained. This avoids the problem of gel formation or incomplete dissolution of pyrimethanil by the organic solvent during the dissolution process, which affects the obtaining of qualified pyrimethanil microemulsions; and also avoids the problem of opacity of pyrimethanil microemulsions under cold storage conditions.

[0011] In one embodiment, the co-solvent includes one or more of ethanol, isopropanol, or n-butanol.

[0012] In one embodiment, the co-solvent is ethanol.

[0013] In one embodiment, the co-solvent is isopropanol.

[0014] In one embodiment, the co-solvent is n-butanol.

[0015] To avoid the problem of opacity in pyrimethanil microemulsion under heat storage, the inventors discovered during experiments that when ethanol, isopropanol, or n-butanol are used as co-solvents, the mixture of pyrimethanil with organic solvents and adjuvants reacts with water to obtain a clear and transparent pyrimethanil microemulsion. This ensures that the pyrimethanil microemulsion does not become opaque under heat storage conditions, resulting in a qualified product.

[0016] In one embodiment, the adjuvant includes a nonionic surfactant and an anionic surfactant, wherein the mass ratio of the nonionic surfactant to the anionic surfactant is (10-20.25):(5-9.75).

[0017] In one embodiment, the additive is composed of a nonionic surfactant and an anionic surfactant, wherein the mass ratio of the nonionic surfactant to the anionic surfactant is (10-20.25):(5-9.75).

[0018] In one embodiment, the nonionic surfactant includes one or a combination of two of 602 or JFC-35.

[0019] In one embodiment, the nonionic surfactants include 602 and JFC-35, and the mass ratio of the nonionic surfactants of type 602 and JFC-35 is (6-12.75):(4-7.5).

[0020] In one embodiment, the nonionic surfactant is composed of 602 and JFC-35, and the mass ratio of the nonionic surfactants 602 and JFC-35 is (6~12.75):

[0021] (4~7.5).

[0022] To avoid the problem of opacity and milky white appearance of pyrimethanil microemulsion during preparation, and to prevent the upper layering of pyrimethanil microemulsion under cold storage conditions, in order to obtain qualified pyrimethanil microemulsion. During the experiment, the inventors discovered that using an adjuvant composed of nonionic and anionic surfactants in a mass ratio of (10–20.25):(5–9.75), with the nonionic surfactants being of types 602 and JFC-35 in a mass ratio of (6–12.75):(4–7.5), resulted in a clear and transparent pyrimethanil microemulsion. This solved the problems of milky opacity and upper layering in pyrimethanil microemulsions. Furthermore, the pyrimethanil microemulsion remained clear and transparent during storage and dilution, thus obtaining a qualified pyrimethanil microemulsion. During the experiment, the inventors discovered that not just any nonionic surfactant can solve the problem of maintaining the clarity and transparency of pyrimethanil microemulsion. Specifically, when using nonionic surfactants of type 601, 1601, or 4000 in combination with JFC-35 as the nonionic surfactant in the pyrimethanil microemulsion, a milky white and opaque appearance occurred during the preparation process, resulting in a failure to obtain a qualified pyrimethanil microemulsion. Furthermore, when using nonionic surfactants of type 602 in combination with AEO-9 as the nonionic surfactant, an opaque appearance occurred during the preparation process, again preventing the acquisition of a qualified pyrimethanil microemulsion.

[0023] In one embodiment, the anionic surfactant comprises a sulfosuccinate salt.

[0024] In one embodiment, the sulfosuccinate salt comprises sodium dioctyl maleate sulfonate.

[0025] In one embodiment, the anionic surfactant is preferably sodium di-2-octyl maleate sulfonate.

[0026] To avoid problems such as paste formation and non-flow during the preparation of pyrimethanil microemulsion, as well as opacity, milky whitening under thermal and dilution conditions, and to obtain a qualified pyrimethanil microemulsion, the inventors discovered during experiments that sulfosuccinate salts are used as an anionic surfactant, particularly sodium di-2-octyl maleate sulfonate, which works in combination with a nonionic surfactant composed of types 602 and JFC-35. The mass ratio of the nonionic surfactant to the anionic surfactant is (10–20.25):(5–9.75). When the nonionic surfactants 602 and JFC-35 are combined in a mass ratio of (6-12.75):(4-7.5), the problems of paste formation and non-flow during the preparation of pyrimethanil microemulsion can be avoided, as well as the problem of opacity. This also prevents the pyrimethanil microemulsion from becoming milky and opaque under thermal and dilution conditions, thus obtaining a qualified pyrimethanil microemulsion. The possible reason is that the nonionic surfactants 602 and JFC-35, combined with sodium di-2-octyl maleate sulfonate and water, can form a bonded interactive network system, improving the stability of the dissolved pyrimethanil in the raw material system.

[0027] During the experiment, the inventors discovered that when the organic solvent specified in this application is composed of 150# solvent oil and N,N-dimethyloctyldecanoate or cyclohexanone, the co-solvent is ethanol, isopropanol or n-butanol, the nonionic surfactant is 602 and JFC-35, and the anionic surfactant is sodium di-2-octyl maleate sulfonate, the pyrimethanil microemulsion obtained from pyrimethanil, organic solvent, co-solvent, adjuvant and water has good stability and can maintain a clear and transparent state during cold storage, hot storage and dilution, thus obtaining a qualified product.

[0028] A second aspect of this invention provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0029] S1. Dissolve pyrimethanil in an organic solvent, then add adjuvants and mix thoroughly to obtain a mixture;

[0030] S2. Add the mixture to water, then add a co-solvent and mix thoroughly to obtain pyrimethanil microemulsion.

[0031] A third aspect of the present invention provides an application of a bensulfuron-methyl microemulsion, which is applied in the field of weed control technology. Attached Figure Description

[0032] Figure 1The image shows the gel-like state that appears in Table 2 of the performance test results.

[0033] Figure 2 The image shows the milky white, opaque state that appears in Table 2 of the performance test results.

[0034] Figure 3 The image shows the clear and transparent state of the room temperature and cold storage conditions as shown in Table 2 of the performance test results.

[0035] Figure 4 The diagram in Table 2 shows the state of the upper layer of the cold storage exhibiting stratification and heterogeneity, as indicated by the performance test results.

[0036] Figure 5 Table 2 shows the clear and transparent and opaque states of the thermal reservoir as presented in the performance test results.

[0037] Figure 6 The image shows the clear and transparent state that appeared after dilution in Table 2 of the performance test results.

[0038] Figure 5 In the middle, #1 is in an opaque state. Figure 5 #2 indicates a clear and transparent state.

[0039] Beneficial effects

[0040] 1. The pyrimethanil microemulsion provided in this application can use water to replace part of the organic solvent, which can increase its green environmental friendliness and improve the safety of production and storage.

[0041] 2. The pyrimethanil microemulsion provided in this application can maintain a transparent storage state, has higher stability, is conducive to the expression of pyrimethanil efficacy, improves weed control effect, and is easier for farmers to use.

[0042] 3. When the organic solvents used in this application include combinations of 150# solvent oil and N,N-dimethyloctyldecanoate or cyclohexanone, a clear and transparent pyrimethanil microemulsion can be obtained, which can improve the expression of pyrimethanil efficacy in the pyrimethanil microemulsion.

[0043] 4. The N,N-dimethyloctyldecylamide to pyrimethanil mass ratio specified in this application is (1-2):1, which can improve the stability of the pyrimethanil microemulsion, obtain a clear and transparent pyrimethanil microemulsion, avoid the problem of gel formation or incomplete dissolution of pyrimethanil by organic solvents during the dissolution process, which would affect the obtaining of qualified pyrimethanil microemulsion; and also avoid the problem of opacity of pyrimethanil microemulsion under cold storage conditions.

[0044] 5. The nonionic surfactants used in this application are specified to be composed of 602 and JFC-35, which can avoid the problem of opacity in appearance during the preparation of pyrimethanil microemulsion, avoid the problem of milky white opacity, avoid the problem of upper layering of pyrimethanil microemulsion under cold storage conditions, and avoid the problem of opacity under cold storage conditions, so as to obtain qualified pyrimethanil microemulsion.

[0045] 6. This application specifies the use of sulfosuccinate salts as anionic surfactants. In particular, when sodium dioctyl maleate sulfonate is selected as an anionic surfactant and used in combination with nonionic surfactants composed of type 602 and JFC-35, problems such as paste formation and non-flowability of pyrimethanil microemulsions during preparation can be avoided, as can the problem of opacity, milky white opacity under heat conditions, and milky white opacity under dilution conditions. This ensures the production of qualified pyrimethanil microemulsions.

[0046] 7. In this application, the organic solvent used is specified to be composed of 150# solvent oil and N,N-dimethyloctyldecanoate or cyclohexanone, the cosolvent used is ethanol, isopropanol or n-butanol, the nonionic surfactant used is model 602 and JFC-35, and the anionic surfactant used is sodium di-2-octyl maleate sulfonate. The pyrimethanil microemulsion obtained by pyrimethanil composed of pyrimethanil, organic solvent, cosolvent, adjuvant and water has good stability and can maintain a clear and transparent state during cold storage, hot storage and dilution, thus obtaining a qualified product. Detailed Implementation

[0047] Group 1 Experiment

[0048] The first group of experiments includes Example 1, Example 2, Example 3, Example 4, and Example 5.

[0049] The first group of experiments provided a pyrimethanil microemulsion, which was prepared from pyrimethanil, organic solvent, co-solvent, additives, and water.

[0050] The organic solvent is composed of N,N-dimethyloctyldecamide and 150# solvent oil.

[0051] The co-solvent is ethanol.

[0052] The additive is composed of nonionic surfactants and anionic surfactants.

[0053] The nonionic surfactant is designated as type 602 or JFC-35. The anionic surfactant is sodium di-2-octyl maleate sulfonate.

[0054] The source of the pyrimethanil is Nantong Jiangshan Pesticide Chemical Co., Ltd., with CAS number 1949837-17-5.

[0055] The CAS number of the N,N-dimethyloctadecanamide is 308062-09-1.

[0056] The CAS number of the 150# solvent oil is 64742-94-5.

[0057] The CAS number for the ethanol is 64-17-5.

[0058] The nonionic surfactant 602 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0059] The nonionic surfactant JFC-35 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0060] The CAS number of the sodium di-2-octyl maleate sulfonate is 577-11-7.

[0061] The water is deionized water.

[0062] Example 1

[0063] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 10% pyrimethanil, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 5% ethanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0064] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0065] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0066] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0067] The third aspect of this embodiment provides an application of pyrimethanil microemulsion in the field of weed control technology.

[0068] Example 2

[0069] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 5% pyrimethanil, 6% N,N-dimethyloctyldecylamide, 6% 150# solvent oil, 10% ethanol, 6% nonionic surfactant 602, 4% nonionic surfactant JFC-35, 5% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0070] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0071] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0072] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0073] The third aspect of this embodiment provides an application of pyrimethanil microemulsion in the field of weed control technology.

[0074] Example 3

[0075] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from the following raw materials: 15% pyrimethanil, 15% N,N-dimethyloctyldecylamide, 15% 150# solvent oil, 8% ethanol, 12.75% nonionic surfactant 602, 7.5% nonionic surfactant JFC-35, 9.75% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0076] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0077] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0078] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0079] The third aspect of this embodiment provides an application of pyrimethanil microemulsion in the field of weed control technology.

[0080] Example 4

[0081] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 5% pyrimethanil, 5% N,N-dimethyloctyldecylamide, 5% 150# solvent oil, 5% ethanol, 8% nonionic surfactant 602, 5% nonionic surfactant JFC-35, 7% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0082] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0083] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0084] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0085] The third aspect of this embodiment provides an application of pyrimethanil microemulsion in the field of weed control technology.

[0086] Example 5

[0087] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 15% pyrimethanil, 15% N,N-dimethyloctyldecylamide, 5% 150# solvent oil, 5% ethanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0088] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0089] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0090] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0091] The third aspect of this embodiment provides an application of pyrimethanil microemulsion in the field of weed control technology.

[0092] Second group of experiments

[0093] The second group of experiments includes Examples 6, 7, and 8.

[0094] The second group of experiments provided a pyrimethanil microemulsion, the raw materials of which consisted of pyrimethanil, organic solvent, co-solvent, additives, and water.

[0095] The organic solvent is composed of N,N-dimethyloctyldecamide and 150# solvent oil.

[0096] The co-solvent includes isopropanol or n-butanol.

[0097] The additive is composed of nonionic surfactants and anionic surfactants.

[0098] The nonionic surfactant is designated as type 602 or JFC-35. The anionic surfactant is sodium di-2-octyl maleate sulfonate.

[0099] The source of the pyrimethanil is Nantong Jiangshan Pesticide Chemical Co., Ltd., with CAS number 1949837-17-5.

[0100] The CAS number of the N,N-dimethyloctadecanamide is 308062-09-1.

[0101] The CAS number of the 150# solvent oil is 64742-94-5.

[0102] The CAS number of the isopropanol is 67-63-0.

[0103] The CAS number of the n-butanol is 71-36-3.

[0104] The nonionic surfactant 602 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0105] The nonionic surfactant JFC-35 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0106] The CAS number of the sodium di-2-octyl maleate sulfonate is 577-11-7.

[0107] The water is deionized water.

[0108] Example 6

[0109] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 10% pyrimethanil, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 6028% nonionic surfactant, JFC-355% nonionic surfactant, 7% sodium di-2-octyl maleate sulfonate, and the remainder being deionized water.

[0110] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0111] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0112] S2. Add the mixture to water and mix thoroughly to obtain pyrimethanil microemulsion.

[0113] Example 7

[0114] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 10% pyrimethanil, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 5% isopropanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0115] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0116] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0117] S2. Add the mixture to water, then add isopropanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0118] The third aspect of this embodiment provides an application of pyrimethanil microemulsion in the field of weed control technology.

[0119] Example 8

[0120] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 10% pyrimethanil, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 5% n-butanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0121] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0122] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0123] S2. Add the mixture to water, then add n-butanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0124] The third aspect of this embodiment provides an application of pyrimethanil microemulsion in the field of weed control technology.

[0125] Third group of experiments

[0126] The third group of experiments includes Examples 9, 10, 11, and 12.

[0127] The third group of experiments provided a pyrimethanil microemulsion, the raw materials of which consisted of pyrimethanil, organic solvent, co-solvent, additives, and water.

[0128] The organic solvent includes 150# solvent oil and one or more combinations of cyclohexanone, ethyl lactate, propylene carbonate, or vinyl sulfite.

[0129] The co-solvent is ethanol.

[0130] The additive is composed of nonionic surfactants and anionic surfactants.

[0131] The nonionic surfactant is designated as type 602 or JFC-35. The anionic surfactant is sodium di-2-octyl maleate sulfonate.

[0132] The source of the pyrimethanil is Nantong Jiangshan Pesticide Chemical Co., Ltd., with CAS number 1949837-17-5.

[0133] The CAS number of the cyclohexanone is 108-94-1.

[0134] The CAS number for ethyl lactate is 97-64-3.

[0135] The CAS number of the propylene carbonate is 108-32-7.

[0136] The CAS number of the vinyl sulfite is 3741-38-6.

[0137] The CAS number of the 150# solvent oil is 64742-94-5.

[0138] The CAS number for the ethanol is 64-17-5.

[0139] The nonionic surfactant 602 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0140] The nonionic surfactant JFC-35 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0141] The CAS number of the sodium di-2-octyl maleate sulfonate is 577-11-7.

[0142] The water is deionized water.

[0143] Example 9

[0144] The first aspect of this embodiment provides a bensulfuron-methyl microemulsion, which, by mass percentage, is prepared from 10% bensulfuron-methyl, 10% cyclohexanone, 10% 150# solvent oil, 5% ethanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0145] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0146] S1. Add pyrimethanil to cyclohexanone and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture.

[0147] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0148] The third aspect of this embodiment provides an application of pyrimethanil microemulsion in the field of weed control technology.

[0149] Example 10

[0150] The first aspect of this embodiment provides a bensulfuron-methyl microemulsion, which, by mass percentage, is prepared from 10% bensulfuron-methyl, 10% ethyl lactate, 10% 150# solvent oil, 5% ethanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% sodium dioctyl maleate sulfonate, and the balance being deionized water.

[0151] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0152] S1. Add pyrimethanil to ethyl lactate and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0153] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0154] Example 11

[0155] The first aspect of this embodiment provides a bensulfuron-methyl microemulsion, which, by mass percentage, is prepared from 10% bensulfuron-methyl, 10% propylene carbonate, 10% 150# solvent oil, 5% ethanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% sodium dioctyl maleate sulfonate, and the remainder being deionized water.

[0156] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0157] S1. Add pyrimethanil to propylene carbonate and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture.

[0158] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0159] Example 12

[0160] The first aspect of this embodiment provides a bensulfuron-methyl microemulsion, which, by mass percentage, is prepared from 10% bensulfuron-methyl, 10% vinyl sulfite, 10% 150# solvent oil, 5% ethanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% sodium dioctyl maleate sulfonate, and the balance being deionized water.

[0161] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0162] S1. Add pyrimethanil to vinyl sulfite and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0163] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0164] Fourth group of experiments

[0165] The fourth group of experiments includes Examples 13, 14, and 15.

[0166] The fourth group of experiments provided a pyrimethanil microemulsion, which was prepared from pyrimethanil, organic solvent, co-solvent, additives, and water.

[0167] The organic solvent is composed of N,N-dimethyloctyldecamide and 150# solvent oil.

[0168] The co-solvent is ethanol.

[0169] The additive is composed of nonionic surfactants and anionic surfactants.

[0170] The nonionic surfactants include one or more combinations of JFC-35, 601, 1601, or 4000.

[0171] The anionic surfactant is sodium dioctyl maleate sulfonate.

[0172] The source of the pyrimethanil is Nantong Jiangshan Pesticide Chemical Co., Ltd., with CAS number 1949837-17-5.

[0173] The CAS number of the N,N-dimethyloctadecanamide is 308062-09-1.

[0174] The CAS number of the 150# solvent oil is 64742-94-5.

[0175] The CAS number for the ethanol is 64-17-5.

[0176] The nonionic surfactant 601 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0177] The nonionic surfactant 1601 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0178] The nonionic surfactant 4000 was purchased from Shanghai Xuezhuo Fine Chemical Co., Ltd.

[0179] The nonionic surfactant JFC-35 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0180] The CAS number of the sodium di-2-octyl maleate sulfonate is 577-11-7.

[0181] The water is deionized water.

[0182] Example 13

[0183] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 10% pyrimethanil, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 5% ethanol, 6018% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0184] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0185] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 601, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0186] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0187] Example 14

[0188] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 10% pyrimethanil, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 5% ethanol, 18% nonionic surfactant 160, 5% nonionic surfactant JFC-35, 7% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0189] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0190] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 1601, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0191] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0192] Example 15

[0193] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 10% pyrimethanil, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 5% ethanol, 8% nonionic surfactant 4000, 5% nonionic surfactant JFC-35, 7% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0194] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0195] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 4000, nonionic surfactant JFC-35 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture.

[0196] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0197] Fifth group of experiments

[0198] The fifth group of experiments includes Example 16.

[0199] The first group of experiments provided a pyrimethanil microemulsion, which was prepared from pyrimethanil, organic solvent, co-solvent, additives, and water.

[0200] The organic solvent is composed of N,N-dimethyloctyldecamide and 150# solvent oil.

[0201] The co-solvent is ethanol.

[0202] The additive is composed of nonionic surfactants and anionic surfactants.

[0203] The nonionic surfactants are designated as 602 and AEO-9. The anionic surfactant is sodium di-2-octyl maleate sulfonate.

[0204] The source of the pyrimethanil is Nantong Jiangshan Pesticide Chemical Co., Ltd., with CAS number 1949837-17-5.

[0205] The CAS number of the N,N-dimethyloctadecanamide is 308062-09-1.

[0206] The CAS number of the 150# solvent oil is 64742-94-5.

[0207] The CAS number for the ethanol is 64-17-5.

[0208] The nonionic surfactant 602 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0209] The nonionic surfactant AEO-9 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0210] The CAS number of the sodium di-2-octyl maleate sulfonate is 577-11-7.

[0211] The water is deionized water.

[0212] Example 16

[0213] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 10% pyrimethanil, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 5% ethanol, 6028% nonionic surfactant, 95% nonionic surfactant AEO-, 7% sodium di-2-octyl maleate sulfonate, and the balance being deionized water.

[0214] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0215] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant AEO-9 and sodium dioctyl maleate sulfonate and mix evenly to obtain a mixture;

[0216] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0217] Sixth experiment

[0218] The sixth group of experiments includes Examples 17, 18, and 19.

[0219] The sixth group of experiments provided a pyrimethanil microemulsion, which was prepared from pyrimethanil, organic solvent, co-solvent, additives, and water.

[0220] The organic solvent is composed of N,N-dimethyloctyldecamide and 150# solvent oil.

[0221] The co-solvent is ethanol.

[0222] The additive is composed of nonionic surfactants and anionic surfactants.

[0223] The nonionic surfactant is designated as type 602 or JFC-35.

[0224] The anionic surfactant includes one or more of calcium dodecylbenzenesulfonate, ammonium salt, or alkylbenzenesulfonate ethanolamine.

[0225] The source of the pyrimethanil is Nantong Jiangshan Pesticide Chemical Co., Ltd., with CAS number 1949837-17-5.

[0226] The CAS number of the N,N-dimethyloctadecanamide is 308062-09-1.

[0227] The CAS number of the 150# solvent oil is 64742-94-5.

[0228] The CAS number for the ethanol is 64-17-5.

[0229] The nonionic surfactant 602 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0230] The nonionic surfactant JFC-35 was purchased from Tangshan Bangxie Fine Additives Co., Ltd.

[0231] The CAS number of the calcium dodecylbenzenesulfonate is 26264-06-2, and the model number is 500#.

[0232] The ammonium salt was purchased from Tangshan Bangxie Fine Additives Co., Ltd., and its model number is H-80.

[0233] The alkylbenzene sulfonate ethanolamine was purchased from Shanghai Xuezhuo Fine Chemical Co., Ltd., and its model number is TSA.

[0234] The water is deionized water.

[0235] Example 17

[0236] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 10% pyrimethanil, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 5% ethanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% calcium dodecylbenzenesulfonate, and the remainder being deionized water.

[0237] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0238] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and calcium dodecylbenzenesulfonate and mix evenly to obtain a mixture;

[0239] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0240] Example 18

[0241] The first aspect of this embodiment provides a bensulfuron-methyl microemulsion, which, by mass percentage, is prepared from 10% bensulfuron-methyl, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 5% ethanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% ammonium salt H-80, and the balance being deionized water.

[0242] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0243] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and ammonium salt H-80 and mix evenly to obtain a mixture;

[0244] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0245] Example 19

[0246] The first aspect of this embodiment provides a pyrimethanil microemulsion, which, by mass percentage, is prepared from 10% pyrimethanil, 10% N,N-dimethyloctyldecylamide, 10% 150# solvent oil, 5% ethanol, 6028% nonionic surfactant, 5% nonionic surfactant JFC-355%, 7% alkylbenzene sulfonate ethanolamine, and the balance being deionized water.

[0247] The second aspect of this embodiment provides a method for preparing a pyrimethanil microemulsion, comprising the following steps:

[0248] S1. Add pyrimethanil to N,N-dimethyloctyldecylamide and 150# solvent oil to dissolve, then add nonionic surfactant 602, nonionic surfactant JFC-35 and alkylbenzene sulfonate ethanolamine and mix evenly to obtain a mixture;

[0249] S2. Add the mixture to water, then add ethanol and mix thoroughly to obtain pyrimethanil microemulsion.

[0250] Performance testing

[0251] The pyrimethanil microemulsions provided in Examples 1-19 were used as samples to test their appearance at room temperature, stability at low temperature, thermal storage stability, and dilution stability according to the test methods provided in Table 1. The test results are shown in Table 2.

[0252] Table 1

[0253]

[0254] Table 2

[0255]

[0256]

[0257] The gel-like state shown in Table 2 is as follows: Figure 1 .

[0258] The milky, opaque state that appears in Table 2 is shown below. Figure 2 .

[0259] Table 2 shows the clear and transparent state observed at room temperature and during cold storage. Figure 3 .

[0260] Table 2 shows the state of stratification and inhomogeneity observed in the upper layer of the cold storage. Figure 4 .

[0261] Table 2 shows the clear and transparent and opaque states of the thermal reservoir. Figure 5 ; Figure 5 In the middle, #1 is in an opaque state. Figure 5 The image shows a clear and transparent state (see figure for reference).

[0262] The clear and transparent state that appeared after dilution is shown in Table 2. Figure 6 .

[0263] As can be seen from the test results in Table 2, the organic solvent used in this application consists of 150# solvent oil and N,N-dimethyloctyldecanoate or cyclohexanone. The co-solvent used includes one or more of ethanol, isopropanol or n-butanol. When the nonionic surfactants used are 602 and JFC-35, and the anionic surfactant used is sodium di-2-octyl maleate sulfonate, the pyrimethanil microemulsion obtained from pyrimethanil, organic solvent, co-solvent, adjuvant, and water has good stability and can maintain a clear and transparent state during cold storage, hot storage, and dilution, thus obtaining a qualified product.

[0264] As can be seen from the test results in Table 2, the organic solvents used in Examples 1-5 of the first group of experiments consisted of 150# solvent oil and N,N-dimethyloctyldecanoate or cyclohexanone. The co-solvents used in the first and second groups of experiments included one or more of ethanol, isopropanol or n-butanol. When using nonionic surfactants composed of 602 and JFC-35 for synergistic action, problems such as paste formation and non-flow during the preparation of pyrimethanil microemulsion can be avoided, as well as the problems of opacity, milky white opacity under thermal conditions, and milky white opacity under dilution conditions. This ensures that a qualified pyrimethanil microemulsion can be obtained.

[0265] As can be seen from the test results in Table 2, when ethanol, isopropanol or n-butanol were not used as co-solvents in Examples 6-8 of the second group of experiments, the obtained bensulfuron-methyl microemulsions would become opaque under heat storage conditions, resulting in the bensulfuron-methyl microemulsions becoming unqualified products.

[0266] As can be seen from the test results in Table 2, when the organic solvent used in this application is composed of 150# solvent oil and N,N-dimethyloctyldecanoate or 150# solvent oil and cyclohexanone, the stability of the pyrimethanil microemulsion can be improved, avoiding the problems of gel formation or incomplete dissolution during the dissolution of pyrimethanil, which would affect the obtaining of qualified pyrimethanil microemulsion; and also avoiding the problem of opacity under cold storage conditions.

[0267] The test results in Table 2 show that in the fourth group of experiments (Examples 13-15), when nonionic surfactants of type 601, 1601, or 4000 were used in combination with JFC-35 as nonionic surfactants in the pyrimethanil microemulsion, a milky white and opaque problem occurred during the preparation of the pyrimethanil microemulsion, and a qualified pyrimethanil microemulsion could not be obtained. When nonionic surfactant type 1601 was used in combination with JFC-35 as a nonionic surfactant, a milky white and opaque problem occurred during the preparation of the pyrimethanil microemulsion, and a qualified pyrimethanil microemulsion could not be obtained. When nonionic surfactant type 601 was used in combination with JFC-35 as a nonionic surfactant, the obtained pyrimethanil microemulsion exhibited upper layering under cold storage conditions, and a homogeneous pyrimethanil microemulsion could not be obtained. When nonionic surfactants 4000 and JFC-35 are used in combination as nonionic surfactants, the resulting pyrimethanil microemulsion becomes opaque under cold storage conditions, and a qualified pyrimethanil microemulsion cannot be obtained.

[0268] As can be seen from the test results in Table 2, when the nonionic surfactants 602 and AEO-9 were used in combination as nonionic surfactants in Example 16 of the fifth group of experiments, the prepared pyrimethanil microemulsion was found to be opaque, and a qualified pyrimethanil microemulsion could not be obtained.

[0269] The test results in Table 2 show that in the sixth group of experiments (Examples 17-19), when ammonium salts were used as the anionic surfactant, the microemulsion of pyrimethanil exhibited problems of paste formation and non-flowability, resulting in the inability to obtain a qualified pyrimethanil microemulsion. When calcium dodecylbenzenesulfonate was used as the anionic surfactant in the pyrimethanil microemulsion, the prepared microemulsion exhibited milky white and opaque properties under heat storage conditions, and this problem also occurred during dilution, again resulting in the inability to obtain a qualified pyrimethanil microemulsion. When ethanolamine alkylbenzenesulfonate was used as the anionic surfactant in the pyrimethanil microemulsion, the microemulsion also exhibited paste formation and non-flowability, resulting in the inability to obtain a qualified pyrimethanil microemulsion.

[0270] Based on the test results in Table 2, qualified pyrimethanil microemulsions will be used in the field of weed control technology.

Claims

1. A pyrimethanil microemulsion, characterized in that, The raw materials for its preparation, by mass percentage, include 5-15% pyrimethanil, 10-25% organic solvent, 5-10% co-solvent, 15-30% auxiliaries, and water as the balance; the organic solvent includes a composition formed by 150# solvent oil and N,N-dimethyloctadecanamide or cyclohexanone.

2. The pyrimethanil microemulsion as described in claim 1, characterized in that, The organic solvent includes 150# solvent oil and N,N-dimethyloctyldecylamide, wherein the mass ratio of N,N-dimethyloctyldecylamide to pyrimethanil is (1-2):

1.

3. The pyrimethanil microemulsion as described in claim 1, characterized in that, The co-solvent includes one or more of ethanol, isopropanol, or n-butanol.

4. The pyrimethanil microemulsion as described in claim 1, characterized in that, The additives include nonionic surfactants and anionic surfactants, wherein the mass ratio of the nonionic surfactants to the anionic surfactants is (10-20.25):(5-9.75).

5. The pyrimethanil microemulsion as described in claim 4, characterized in that, The nonionic surfactant includes one or a combination of two of 602 or JFC-35.

6. The pyrimethanil microemulsion as described in claim 5, characterized in that, The nonionic surfactants include 602 and JFC-35, and the mass ratio of the nonionic surfactants 602 and JFC-35 is (6~12.75):(4~7.5).

7. The pyrimethanil microemulsion as described in claim 4, characterized in that, The anionic surfactant includes sulfosuccinate salts.

8. The pyrimethanil microemulsion as described in claim 7, characterized in that, The sulfosuccinate salts include sodium dioctyl maleate sulfonate.

9. A method for preparing the pyrimethanil microemulsion as described in any one of claims 1-8, characterized in that, Includes the following steps: S1. Dissolve pyrimethanil in an organic solvent, then add adjuvants and mix thoroughly to obtain a mixture; S2. Add the mixture to water, then add a co-solvent and mix thoroughly to obtain pyrimethanil microemulsion.

10. An application of the pyrimethanil microemulsion as described in any one of claims 1-8, characterized in that, The pyrimethanil microemulsion is used in the field of weed control technology.

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