A synergistic insecticide of pyriproxyfen and lufenuron, its preparation method and application
By combining the active agents of pyriproxyfen and lufenuron with specific surfactant solvents, a stable microemulsion is formed, which solves the problem of turbidity of insecticides under low and high temperature environments, improves the utilization rate and control timeliness of the agent, and reduces the risk of toxicity.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- HEMEISI (SHANDONG) PLANT PROTECTION CO LTD
- Filing Date
- 2026-02-28
- Publication Date
- 2026-06-02
AI Technical Summary
Existing insecticides are prone to turbidity and stratification in low and high temperature environments. Single-agent products can only target a certain stage of the pest's life cycle, resulting in a short duration of effectiveness. Furthermore, traditional emulsifiable concentrates or suspensions suffer from severe droplet rebound after spraying, leading to low pesticide utilization.
A combination of pyriproxyfen and lufenuron active agents in a weight ratio of (1-5):(1-5) and a specific combination of surfactants and solvents is used to form a stable microemulsion, which improves the stability and delivery efficiency of the agent and enhances the efficacy.
This technology achieves drug stability under different temperature conditions, improves drug utilization and control timeliness, enhances efficacy, and reduces the risk of toxicity to the environment and users.
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Figure CN122123377A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of insecticides, specifically to a synergistic insecticide of pyriproxyfen and lufenuron, its preparation method, and its application. Background Technology
[0002] Control of lepidopteran pests such as the diamondback moth primarily employs a combination of ovicidal and adult-killing methods. Existing control products suffer from stability issues; insecticidal microemulsions are prone to turbidity and stratification in low and high temperature environments. Current single-agent insecticides only target a specific stage of the pest's life cycle; for example, pyriproxyfen primarily kills eggs, and lufenuron primarily inhibits larval molting, but they lack synergistic effects, resulting in short-lasting efficacy. Unlike traditional emulsifiable concentrates or suspensions, which are prone to droplet bounce after spraying, lufenuron has a large contact angle with the target surface and a small spreading area, leading to low pesticide utilization. Therefore, developing an insecticide with high stability, synergistic ovicidal effect, high delivery efficiency, and environmental safety is crucial.
[0003] Chinese invention patent application CN114097794A discloses a synergistic composition containing pyrazole amide compounds. Utilizing the different action sites and mechanisms of action of pathogens, the combination can act on pathogens at multiple sites, broadening the fungicidal spectrum and improving efficacy. However, it is mostly used in the preparation of fungicides, with poor efficacy against pests. Chinese invention patent CN114467949B discloses a synergistic composition containing quinolone compounds and its application. The combination of fungicides and insecticides has a synergistic effect, improving control efficacy and simultaneously preventing crop diseases and pests, with better results. However, its efficacy against pests is still poor. Summary of the Invention
[0004] In order to develop a highly stable, synergistic insecticide with insecticidal and ovicidal effects, high delivery efficiency, and environmental safety, the first aspect of the present invention provides a synergistic insecticide of pyriproxyfen and lufenuron, the raw materials for preparation including active agent, surfactant, solvent, antifreeze and deionized water, wherein the active agent includes pyriproxyfen and lufenuron, and the weight ratio of pyriproxyfen and lufenuron is (1-5):(1-5).
[0005] This application employs a combination of pyriproxyfen and lufenuron, which achieves superior control efficacy compared to single-agent pesticides and extends the duration of insecticide control. This is likely because pyriproxyfen acts on the developmental stage of insect eggs, preventing normal hatching, while lufenuron inhibits the molting process of insect larvae, blocking their life cycle and thus preventing insect reproduction at its source, significantly reducing the insect population. Furthermore, the weight ratio of pyriproxyfen and lufenuron (1-5):(1-5) creates a synergistic effect targeting both eggs and larvae, with complementary mechanisms, avoiding the risk of resistance from single pesticides and extending the duration of insect control.
[0006] In one embodiment, the weight ratio of pyriproxyfen to lufenuron is (1-3):(1-3).
[0007] In one embodiment, the weight ratio of pyriproxyfen to lufenuron is 1:1.
[0008] In one embodiment, the mass fraction of the active agent in the synergistic insecticide of pyriproxyfen and lufenuron is 10-30%.
[0009] In one embodiment, the mass fraction of the active agent in the synergistic insecticide of pyriproxyfen and lufenuron is 15-25%.
[0010] In one embodiment, the active agent in the synergistic insecticide of pyriproxyfen and lufenuron is 20% by mass.
[0011] In one embodiment, the surfactant includes nonionic surfactants and anionic surfactants, wherein the anionic surfactant includes at least one of alkyl sulfonates or alkylbenzene sulfonates.
[0012] In one embodiment, the alkyl sulfonate is at least one of alkylphenol polyoxyethylene ether sulfonates; the alkylbenzene sulfonate is at least one of dodecylbenzene sulfonates.
[0013] In one embodiment, the nonionic surfactant includes at least one of styrene-phenol polyoxyethylene ether phosphate triethanolamine salt, nonylphenol polyoxyethylene ether, octylphenol polyoxyethylene ether, lauryl alcohol polyoxyethylene ether, oleyl alcohol polyoxyethylene ether, and polyoxyethylene-polyoxypropylene block copolymer.
[0014] In one embodiment, the surfactant includes alkylphenol polyoxyethylene ether sulfonate, tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt, and dodecylbenzene sulfonate.
[0015] In one embodiment, the surfactant includes alkylphenol polyoxyethylene ether sulfonate, tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt, and calcium dodecylbenzenesulfonate.
[0016] In one embodiment, the weight ratio of the alkylphenol polyoxyethylene ether sulfonate, tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt, and dodecylbenzene sulfonate is (1-5):(1-5):(15-25).
[0017] In one embodiment, the weight ratio of the alkylphenol polyoxyethylene ether sulfonate, tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt, and dodecylbenzene sulfonate is (3-5):(3-5):(18-23).
[0018] In one embodiment, the weight ratio of the alkylphenol polyoxyethylene ether sulfonate, tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt, and dodecylbenzene sulfonate is 5:5:20.
[0019] In one embodiment, the solvent comprises a combination of cyclohexanone and N-methylpyrrolidone.
[0020] In one embodiment, the weight ratio of cyclohexanone to N-methylpyrrolidone is (5-15):(5-15).
[0021] In one embodiment, the weight ratio of cyclohexanone to N-methylpyrrolidone is 10:10.
[0022] In one embodiment, the antifreeze is n-butanol.
[0023] As one implementation method, the raw materials prepared by weight percentage include 10-30% active agent, 20-40% surfactant, 10-30% solvent, 3-8% antifreeze, and deionized water to make up to 100%.
[0024] In one embodiment, the raw materials prepared by weight percentage include 20.5% active pharmaceutical ingredient, 30% surfactant, 20% solvent, 5% antifreeze, and deionized water to make up to 100%.
[0025] A second aspect of the present invention provides a method for preparing a synergistic insecticide of pyriproxyfen and lufenuron, comprising the following steps: The active agent and solvent are mixed and stirred until completely dissolved. Then, surfactant and antifreeze are added and stirred evenly. Finally, deionized water is added and mixed evenly to obtain a synergistic insecticide of pyriproxyfen and lufenuron.
[0026] A third aspect of the present invention provides a method for controlling pests, wherein the above-mentioned pyriproxyfen and lufenuron synergistic insecticide is diluted and sprayed on plants damaged by pests.
[0027] Compared with the prior art, the present invention has the following beneficial effects: (1) The synergistic insecticide of pyriproxyfen and lufenuron described in this invention uses a combination of active agents of pyriproxyfen and lufenuron, and adopts a weight ratio of (1-5):(1-5), which can achieve a control effect superior to that of single agents and prolong the control time of insecticide.
[0028] (2) The synergistic insecticide of pyriproxyfen and lufenuron described in this invention uses a surfactant combination of alkylphenol polyoxyethylene ether sulfonate, tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt and calcium dodecylbenzenesulfonate. The microemulsion has high stability and no turbidity under hot storage and cold storage conditions.
[0029] (3) The synergistic insecticide of pyriproxyfen and lufenuron described in this invention uses alkylphenol polyoxyethylene ether sulfonate, tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt and calcium dodecylbenzenesulfonate in a weight ratio of 5:5:20, which can improve the dissolution rate, make the active ingredients easier to deliver to the target site, and enhance the efficacy and bioavailability; and the droplets formed after the microemulsion is diluted have low surface tension, which can produce spray droplets of appropriate size, with a small contact angle with the target surface, a large spreading area, and reduced droplet rebound. The liquid crystal phase formed after evaporation can firmly adhere to the target surface, improving the utilization rate; the effective particle size in the formed spray droplets is extremely small, at the nanometer level, which can overcome the capillary resistance of the epidermis of animals and plants, better penetrate into the biological tissue, and further enhance the efficacy and drug effect.
[0030] (4) The synergistic insecticide of pyriproxyfen and lufenuron described in this invention uses a solvent combination of cyclohexanone and N-methylpyrrolidone and a weight ratio of 10:10, which can completely dissolve pyriproxyfen and lufenuron in the microemulsion and maintain a stable pesticide content fraction.
[0031] (5) The synergistic insecticide of pyriproxyfen and lufenuron described in this invention uses water as the dispersion medium, which reduces the volatilization of toxic and harmful gases and reduces the risk of toxicity to the environment, animals and plants and users, which is in line with the concept of green and sustainable development. The processing technology is simple and can be used in existing emulsifiable oil production lines. It has good fluidity and is easy to package and transport. It avoids the use of a large amount of organic solvents, reduces production costs, and has a high flash point and strong safety, which reduces transportation and storage risks and has high overall economic benefits. Attached Figure Description
[0032] Figure 1 Photographs of the synergistic insecticides of pyriproxyfen and lufenuron in Comparative Example 1 after heat storage. Figure 2 Photographs of the synergistic insecticides of pyriproxyfen and lufenuron in Comparative Example 1 after cold storage. Figure 3 Photographs of the synergistic insecticides of pyriproxyfen and lufenuron in Comparative Example 2 after heat storage. Figure 4 Photographs of the synergistic insecticides of pyriproxyfen and lufenuron in Comparative Example 2 after cold storage. Figure 5 Photographs of the synergistic insecticides of pyriproxyfen and lufenuron in Comparative Example 3 after heat storage. Figure 6 Photographs of the synergistic insecticides of pyriproxyfen and lufenuron in Comparative Example 3 after cold storage. Figure 7 Photographs of the synergistic insecticide of pyriproxyfen and lufenuron in Example 1 after heat storage; Figure 8This is a photograph of the synergistic insecticide of pyriproxyfen and lufenuron in Example 1 after cold storage. Detailed Implementation
[0033] Example 1 A synergistic insecticide of pyriproxyfen and lufenuron is prepared by means of raw materials including 20.5% active agent, 30% surfactant, 20% solvent, 5% antifreeze and deionized water to make up to 100% by weight.
[0034] The active agent comprises pyriproxyfen and lufenuron, wherein the weight ratio of pyriproxyfen to lufenuron is 10.3:10.2. The pyriproxyfen is a 97wt% technical grade, purchased from Nantong Shi Chemical Co., Ltd.; the lufenuron is a 98wt% technical grade, purchased from Anhui Ningyitai Technology Co., Ltd.
[0035] The surfactant comprises alkylphenol polyoxyethylene ether sulfonate, tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt, and calcium dodecylbenzenesulfonate in a weight ratio of 5:5:20; the alkylphenol polyoxyethylene ether sulfonate is purchased from Shandong Yunmiao, brand name RS-ME628; the tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt is purchased from Nantong Xinde, brand name DY-601PT.
[0036] The solvent comprises a combination of cyclohexanone and N-methylpyrrolidone in a weight ratio of 10:10.
[0037] The antifreeze is n-butanol.
[0038] A method for preparing a synergistic insecticide of pyriproxyfen and lufenuron includes the following steps: The active agent and solvent are mixed and stirred until completely dissolved. Then, surfactant and antifreeze are added and stirred evenly. Finally, deionized water is added and mixed evenly to obtain a synergistic insecticide of pyriproxyfen and lufenuron.
[0039] Comparative Example 1 A synergistic insecticide of pyriproxyfen and lufenuron is prepared by means of raw materials including 20.5% active agent, 25% surfactant, 20% solvent, 5% antifreeze and deionized water to make up to 100% by weight.
[0040] The active agent comprises pyriproxyfen and lufenuron, wherein the weight ratio of pyriproxyfen to lufenuron is 10.3:10.2. The pyriproxyfen is a technical grade of pyriproxyfen with a content of 97 wt%; the lufenuron is a technical grade of lufenuron with a content of 98 wt%.
[0041] The surfactant comprises castor oil polyoxyethylene ether, alkylphenol polyoxyethylene ether sulfonate, and tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt in a weight ratio of 5:5:15; the castor oil polyoxyethylene ether is purchased from Nantong Xinde, brand name DY-BY-125; the alkylphenol polyoxyethylene ether sulfonate is purchased from Nantong Xinde, brand name DY-601SA; and the tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt is purchased from Nantong Xinde, brand name DY-601PT.
[0042] The solvent comprises a combination of cyclohexanone and N-methylpyrrolidone in a weight ratio of 10:10.
[0043] The antifreeze is n-butanol.
[0044] A method for preparing a synergistic insecticide of pyriproxyfen and lufenuron includes the following steps: The active agent and solvent are mixed and stirred until completely dissolved. Then, surfactant and antifreeze are added and stirred evenly. Finally, deionized water is added and mixed evenly to obtain a synergistic insecticide of pyriproxyfen and lufenuron.
[0045] Comparative Example 2 A synergistic insecticide of pyriproxyfen and lufenuron is prepared by means of raw materials including 20.5% active agent, 25% surfactant, 20% solvent, 5% antifreeze and deionized water to make up to 100% by weight.
[0046] The active agent comprises pyriproxyfen and lufenuron, wherein the weight ratio of pyriproxyfen to lufenuron is 10.3:10.2. The pyriproxyfen is a technical grade of pyriproxyfen with a content of 97 wt%; the lufenuron is a technical grade of lufenuron with a content of 98 wt%.
[0047] The surfactant comprises a combination of fatty alcohol polyoxyethylene ether, calcium dodecylbenzenesulfonate, and plant alkyl betaine in a weight ratio of 5:5:15; the fatty alcohol polyoxyethylene ether was purchased from Nantong Xinde and its brand name is DYMOA / 9; the plant alkyl betaine was purchased from Peixian Zhunong New Materials and its brand name is CAB-35.
[0048] The solvent comprises a combination of cyclohexanone and N-methylpyrrolidone in a weight ratio of 10:10.
[0049] The antifreeze is n-butanol.
[0050] A method for preparing a synergistic insecticide of pyriproxyfen and lufenuron includes the following steps: The active agent and solvent are mixed and stirred until completely dissolved. Then, surfactant and antifreeze are added and stirred evenly. Finally, deionized water is added and mixed evenly to obtain a synergistic insecticide of pyriproxyfen and lufenuron.
[0051] Comparative Example 3 A synergistic insecticide of pyriproxyfen and lufenuron is prepared by means of raw materials including 20.5% active agent, 25% surfactant, 20% solvent, 5% antifreeze and deionized water to make up to 100% by weight.
[0052] The active agent comprises pyriproxyfen and lufenuron, wherein the weight ratio of pyriproxyfen to lufenuron is 10.3:10.2. The pyriproxyfen is a technical grade of pyriproxyfen with a content of 97 wt%; the lufenuron is a technical grade of lufenuron with a content of 98 wt%.
[0053] The surfactant comprises a combination of alkylphenol polyoxyethylene ether formaldehyde condensate sulfate, polyoxypropylene ether block copolymer, and calcium dodecylbenzenesulfonate in a weight ratio of 5:5:15; the alkylphenol polyoxyethylene ether formaldehyde condensate sulfate was purchased from Beijing Hanmok, brand name DSC-1022; the polyoxypropylene ether block copolymer was purchased from Beijing Hanmok, brand name DSC-5005.
[0054] The solvent comprises a combination of cyclohexanone and N-methylpyrrolidone in a weight ratio of 10:10.
[0055] The antifreeze is n-butanol.
[0056] A method for preparing a synergistic insecticide of pyriproxyfen and lufenuron includes the following steps: The active agent and solvent are mixed and stirred until completely dissolved. Then, surfactant and antifreeze are added and stirred evenly. Finally, deionized water is added and mixed evenly to obtain a synergistic insecticide of pyriproxyfen and lufenuron.
[0057] Comparative Example 4 A suspension insecticide, purchased from Jiangmen Daguangming Agricultural Chemical Xinhui Co., Ltd., is a pyriproxyfen sanitary insecticide.
[0058] Comparative Example 5 A microemulsion insecticide, purchased from Guangxi Tianyuan Biochemical Co., Ltd., is a lufenuron insecticide.
[0059] Comparative Example 6 A suspension insecticide, purchased from Shanghai Shengnong Biochemical Products Co., Ltd., is a pyriproxyfen·chlorfenapyr insecticide.
[0060] Performance testing 1. Efficacy Test The synergistic insecticide of pyriproxyfen and lufenuron prepared in Example 1 was applied in Shanggao Township, Taishan District, Tai'an City, Shandong Province in April-May 2025. The experimental site had a history of severe diamondback moth infestations in cabbage.
[0061] The experimental reagents and dosages are detailed in Table 1. Each treatment was replicated four times, with a plot area of 30 m².2 A total of 16 plots were constructed, randomly arranged in blocks. Unmanned aerial vehicle (UAV) spraying was used, with a pesticide application rate of 7.5 L / hm². 2 The entire plant was sprayed evenly. The first application was performed at the initial stage of diamondback moth infestation in cabbage, followed by a second application 7 days later. A water treatment was used as a blank control. The initial disease incidence was assessed before application, and the control effect was assessed before and 14 days after the second application. The experimental results are shown in Table 1 below.
[0062] Table 1
[0063] 2. Stability Test: The synergistic insecticides of pyriproxyfen and lufenuron prepared in the examples and comparative examples were stored at 54°C for 14 days, and the results were observed. The synergistic insecticides of pyriproxyfen and lufenuron prepared in the examples and comparative examples were stored at 0°C for 7 days, and the results were observed. A photograph of the synergistic insecticide of pyriproxyfen and lufenuron in Comparative Example 1 after heat storage is shown below. Figure 1 See photos after cold storage. Figure 2 Its turbidity after heat storage and normal condition after refrigeration; photos of the synergistic insecticide of pyriproxyfen and lufenuron in Comparative Example 2 after heat storage are shown below. Figure 3 See photos after cold storage. Figure 4 Its turbidity after heat storage and normal condition after refrigeration; photos of the synergistic insecticide of pyriproxyfen and lufenuron in Comparative Example 3 after heat storage are shown below. Figure 5 See photos after cold storage. Figure 6 Its turbidity was observed under refrigeration, but normal under heat storage. A photograph of the synergistic insecticide of pyriproxyfen and lufenuron in Example 1 after heat storage is shown below. Figure 7 See photos after cold storage. Figure 8 The physicochemical properties of the synergistic insecticide of pyriproxyfen and lufenuron in Example 1 are shown in Table 2.
[0064] Table 2
Claims
1. A synergistic insecticide of pyriproxyfen and lufenuron, characterized in that, The raw materials for preparation include active pharmaceutical agents, surfactants, solvents, antifreeze agents and deionized water. The active pharmaceutical agents include pyriproxyfen and lufenuron, and the weight ratio of pyriproxyfen to lufenuron is (1-5):(1-5).
2. The synergistic insecticide of pyriproxyfen and lufenuron according to claim 1, characterized in that, The active ingredient in the synergistic insecticide has a mass fraction of 10-30%.
3. The synergistic insecticide of pyriproxyfen and lufenuron according to claim 1, characterized in that, The surfactants include nonionic surfactants and anionic surfactants, and the anionic surfactants include at least one of alkyl sulfonates or alkylbenzene sulfonates.
4. The synergistic insecticide of pyriproxyfen and lufenuron according to claim 3, characterized in that, The alkyl sulfonate is at least one of alkylphenol polyoxyethylene ether sulfonates; the alkylbenzene sulfonate is at least one of dodecylbenzene sulfonates.
5. The synergistic insecticide of pyriproxyfen and lufenuron according to claim 3, characterized in that, The nonionic surfactant includes at least one of the following: tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt, nonylphenol polyoxyethylene ether, octylphenol polyoxyethylene ether, lauryl alcohol polyoxyethylene ether, oleyl alcohol polyoxyethylene ether, and polyoxyethylene-polyoxypropylene block copolymer.
6. The synergistic insecticide of pyriproxyfen and lufenuron according to claim 1, characterized in that, The surfactants include alkylphenol polyoxyethylene ether sulfonate, tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt, and dodecylbenzene sulfonate.
7. The synergistic insecticide of pyriproxyfen and lufenuron according to claim 6, characterized in that, The weight ratio of the alkylphenol polyoxyethylene ether sulfonate, tristyrene-phenol polyoxyethylene ether phosphate triethanolamine salt, and dodecylbenzene sulfonate is (1-5):(1-5):(15-25).
8. The synergistic insecticide of pyriproxyfen and lufenuron according to claim 1, characterized in that, The raw materials prepared by weight percentage include 10-30% active agent, 20-40% surfactant, 10-30% solvent, 3-8% antifreeze, and deionized water to make up to 100%.
9. A method for preparing a synergistic insecticide of pyriproxyfen and lufenuron according to any one of claims 1-8, characterized in that, Includes the following steps: The active agent and solvent are mixed and stirred until completely dissolved. Then, surfactant and antifreeze are added and stirred evenly. Finally, deionized water is added and mixed evenly to obtain a synergistic insecticide of pyriproxyfen and lufenuron.
10. A method for controlling pests, characterized in that, The synergistic insecticide of pyriproxyfen and lufenuron as described in any one of claims 1-8 is diluted and sprayed on plants infested by pests.