阅读说明：本技术 一种噁唑酰草胺乳油及其制备方法 (Metamifop emulsifiable concentrate and preparation method thereof ) 是由 金鑫雷 范伟赠 徐勇存 张平 陈红丹 陈丰喜 于 2020-12-18 设计创作，主要内容包括：本发明涉及一种噁唑酰草胺乳油及其制备方法和应用,属于农药制剂领域。有效成分为噁唑酰草胺,按照重量百分比原料组成：噁唑酰草胺1％-30％,复合乳化剂1-40％、助溶剂1-20％、安全剂0.05-10％,余量为溶剂。所述复合乳化剂由十二烷基苯磺酸盐、苯乙烯基酚聚氧乙烯醚和异构十三醇聚氧乙烯醚组成,所述十二烷基苯磺酸盐、苯乙烯基酚聚氧乙烯醚和异构十三醇聚氧乙烯醚的重量比为1:1-10:2-20,且所述助溶剂为苯乙酮,安全剂为：2-甲氧基-N-[[4-[[(甲基氨基)羰基]氨基]苯基]磺酰基]苯甲酰胺。本发明制备的噁唑酰草胺乳油具有性质稳定、加工工艺简单、低毒、环保、安全性高等优点,具有良好的社会和生态效益。(The invention relates to metamifop emulsifiable concentrate and a preparation method and application thereof, belonging to the field of pesticide preparations. The active ingredient is metamifop, and the composition comprises the following raw materials in percentage by weight: 1 to 30 percent of metamifop, 1 to 40 percent of compound emulsifier, 1 to 20 percent of cosolvent, 0.05 to 10 percent of safener and the balance of solvent. The composite emulsifier consists of dodecyl benzene sulfonate, styryl phenol polyoxyethylene ether and isomeric tridecanol polyoxyethylene ether, the weight ratio of the dodecyl benzene sulfonate, the styryl phenol polyoxyethylene ether and the isomeric tridecanol polyoxyethylene ether is 1:1-10:2-20, the cosolvent is acetophenone, and the safety agent is: 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide. The metamifop emulsifiable concentrate prepared by the invention has the advantages of stable property, simple processing technology, low toxicity, environmental protection, high safety and the like, and has good social and ecological benefits.)

1. The metamifop emulsifiable concentrate is characterized by comprising the following components in percentage by weight: 1-30% of metamifop, 1-40% of composite emulsifier, 1-20% of cosolvent, 0.05-10% of safener and the balance of solvent. The composite emulsifier consists of dodecyl benzene sulfonate, styryl phenol polyoxyethylene ether and isomeric tridecanol polyoxyethylene ether, the weight ratio of the dodecyl benzene sulfonate, the styryl phenol polyoxyethylene ether and the isomeric tridecanol polyoxyethylene ether is 1:1-10:2-20, the cosolvent is acetophenone, and the safety agent is: 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide.

2. The metamifop emulsifiable concentrate as claimed in claim 1, wherein: the composition comprises the following components in percentage by weight: 10% of metamifop, 10-35% of composite emulsifier, 5-20% of cosolvent, 0.5% of safener and the balance of solvent; the weight ratio of dodecyl benzene sulfonate, styryl phenol polyoxyethylene ether and isomeric tridecanol polyoxyethylene ether in the composite emulsifier is 1:5: 6.

3. The metamifop emulsifiable concentrate as claimed in claim 1, wherein: the composition comprises the following components in percentage by weight: 20% of metamifop, 10-25% of composite emulsifier, 10-20% of cosolvent, 1% of safener and the balance of solvent; the weight ratio of dodecyl benzene sulfonate, styryl phenol polyoxyethylene ether and isomeric tridecanol polyoxyethylene ether in the composite emulsifier is 1:4: 7.

4. An metamifop emulsifiable concentrate as claimed in any one of claims 1-3, wherein said safener is 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide.

5. An metamifop emulsifiable concentrate as claimed in any one of claims 1-3, wherein said cosolvent is acetophenone.

6. An metamifop emulsifiable concentrate as claimed in any one of claims 1-3, characterized in that: the solvent comprises one or more of cyclohexanone, butyl lactate, butyl acetate, dimethyl sulfoxide, N-dimethyl pelargonide, N-methyl pyrrolidone, solvent oil S-150, ethylene glycol butyl ether acetate, 1, 4-butyrolactone, diethylene glycol butyl ether, isooctyl acetate, N-dimethylformamide, isophorone, solvent oil S-200, propylene glycol butyl ether, ethanol, tetrahydrofurfuryl alcohol, solvent oil S-100A, ethylene glycol monobutyl ether and butyl benzoate, and the preferable solvent is solvent oil S-150.

7. A process for the preparation of an metamifop emulsifiable concentrate as claimed in any one of claims 1-6, which comprises: adding metered metamifop, a safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, a cosolvent acetophenone and a solvent into a blending kettle, stirring for dissolving, adding a metered emulsifier, stirring until the materials are completely and uniformly dissolved, filtering, and detecting to obtain the metamifop missible oil.

8. Use of an metamifop emulsifiable concentrate according to claims 1-6 for the control of grassy weeds.

9. The application of the metamifop emulsifiable concentrate as claimed in claim 8, wherein the grassy weeds are barnyard grass and crabgrass.

The technical field is as follows:

the invention belongs to the field of pesticide formulations, and particularly relates to metamifop emulsifiable concentrate as well as a preparation method and application thereof

Technical Field

The emulsifiable concentrate is a formulation in pesticide preparations. The homogeneous transparent oily liquid is prepared through dissolving original pesticide in organic solvent, adding emulsifier, diluting with water to form stable emulsion and spraying. The missible oil is the formulation with the highest use efficiency at the present stage.

Compared with other pesticide formulations, the missible oil has the following characteristics: the processing technology is simple, and the transparent and homogeneous oily liquid generally has good chemical and physical stability, is not easy to decompose, turbid, delaminate, precipitate and the like under the closed condition at normal temperature, and has good storage stability. The pesticide which can be processed into emulsifiable solution has a plurality of varieties and a wide application range, is a very important formulation in the pesticide in China, and has the characteristics of long lasting period and high biological activity compared with other pesticide formulations.

Metamifop (metamifop), chemical name (R) -2- { (4-chloro-1, 3-benzoxazol-2-yloxy) phenoxy } -2' -fluoro-N-methylpropionanilide, cas accession No.: 256412-89-2.

Metamifop belongs to aryloxy phenoxy propionate herbicides, and the action mechanism of the metamifop is to inhibit the biosynthesis of acetyl coenzyme A carboxylase. After the herbicide is applied, the sensitive weeds have green leaves and growth is inhibited, and the weeds die after 2 weeks. The herbicide is mainly used for preventing and killing most annual gramineous weeds such as barnyard grass, large crabgrass, moleplant seeds, eleusine indica and the like in rice transplanting fields and direct seeding fields, and has a great development prospect.

The metamifop needs to be used after three leaves of rice are one heart, and serious phytotoxicity can be caused at low temperature or when the leaves are too old. The safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide is creatively added, so that the safety of the metamifop to the rice can be greatly improved, and the safener has higher economic value.

Disclosure of Invention

The invention aims to provide the metamifop emulsifiable concentrate with high efficiency, environmental protection and high safety, and the preparation method and the application thereof, in order to achieve the aim, the invention adopts the technical scheme that:

(1) on the one hand, the metamifop emulsifiable concentrate with high efficiency, environmental protection and high safety is provided, and comprises the following components in percentage by weight: 1-30% of metamifop, 1-40% of composite emulsifier, 1-20% of cosolvent, 0.05-10% of safener and the balance of solvent.

(2) The composite emulsifier is composed of dodecyl benzene sulfonate, styryl phenol polyoxyethylene ether and isomeric tridecanol polyoxyethylene ether, and the weight ratio of the dodecyl benzene sulfonate, the styryl phenol polyoxyethylene ether and the isomeric tridecanol polyoxyethylene ether is 1:1-10: 2-20.

(3) Preferably, the efficient, environment-friendly and safe metamifop emulsifiable concentrate consists of the following components in percentage by weight: 10% of metamifop, 10-35% of composite emulsifier, 5-10% of cosolvent, 0.5% of safener and the balance of solvent; the weight ratio of the calcium dodecyl benzene sulfonate, the phenethyl phenol polyoxyethylene ether and the isomeric tridecanol polyoxyethylene ether in the composite emulsifier is 1:5:6

(4) Preferably, the efficient, environment-friendly and safe metamifop emulsifiable concentrate consists of the following components in percentage by weight: 20% of metamifop, 10-25% of composite emulsifier, 10-20% of cosolvent, 1% of safener and the balance of solvent; the weight ratio of dodecyl benzene sulfonate, styryl phenol polyoxyethylene ether and isomeric tridecanol polyoxyethylene ether in the composite emulsifier is 1:4: 7.

(5) Preferably, the cosolvent is acetophenone, so that the stability of the pesticide raw material in an organic solvent and water is improved.

(6) Preferably, the safener is 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide.

(7) Preferably, the solvent comprises one or more of cyclohexanone, butyl lactate, butyl acetate, dimethyl sulfoxide, N-dimethyl pelargonide, N-methyl pyrrolidone, solvent oil S-150, ethylene glycol butyl ether acetate, 1, 4-butyrolactone, diethylene glycol butyl ether, isooctyl acetate, N-dimethyl formamide, isophorone, solvent oil S-200, propylene glycol butyl ether, ethanol, tetrahydrofurfuryl alcohol, solvent oil S-100A, ethylene glycol monobutyl ether and butyl benzoate, and the preferred solvent is solvent oil S-150.

(8) On the other hand, the invention also provides a preparation method of the metamifop emulsifiable concentrate, which comprises the following steps: adding metered metamifop, a safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, a cosolvent acetophenone and a solvent into a blending kettle, stirring for dissolving, adding a metered emulsifier, stirring until the materials are completely and uniformly dissolved, filtering, and detecting to obtain the metamifop missible oil.

(9) On the other hand, the invention also provides the metamifop emulsifiable concentrate which is applied to preventing and treating gramineous weeds and improving the safety of rice.

(10) Further, the grassy weeds are barnyard grass and large crabgrass.

The invention has the following beneficial effects:

1. the invention optimizes the components and the proportion of the emulsifier, and the screened composite emulsifier has good emulsifying effect and wetting effect and stable emulsion performance.

2. The invention selects the specific cosolvent, and the prepared missible oil can automatically disperse in water and has good stability.

3. The invention selects the specific safener, and greatly improves the safety of the medicament compared with the safety agent which is not added.

4. Compared with the single emulsifier, the invention has more obvious synergistic effect.

The specific implementation mode is as follows:

the present invention is further illustrated by the following examples, which are not intended to limit the invention to these embodiments. It will be appreciated by those skilled in the art that the present invention encompasses all alternatives, modifications, and equivalents as may be included within the scope of the claims.

The preparation method comprises the steps of adding metered metamifop, a safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, a cosolvent acetophenone and a solvent into a blending kettle, stirring for dissolving, adding a metered emulsifier, stirring until the materials are completely and uniformly dissolved, filtering, and obtaining the metamifop missible oil after the detection is qualified. In the examples below, all percentages are by weight unless otherwise indicated.

1. Detailed description of the preferred embodiments

Example 110% Oxazolecarboxamide emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 20% of composite emulsifier, 10% of cosolvent acetophenone, 0.5% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide and solvent oil S-150 in balance. Wherein the weight ratio of the composite emulsifier to the dodecyl benzene sulfonate, the styryl phenol polyoxyethylene ether and the isomeric tridecanol polyoxyethylene ether is 1:5: 6.

Example 220% Oxazolecarboxamide emulsifiable concentrate

The 20% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 20% of metamifop, 20% of composite emulsifier, 15% of cosolvent acetophenone, 1% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide and the balance of solvent oil S-150. Wherein the composite emulsifier is dodecyl benzene sulfonate, styryl phenol polyoxyethylene ether and isomeric tridecanol polyoxyethylene ether with the weight ratio of 1:4:7

Example 315% Oxazolecarboxamide emulsifiable concentrate

The 15% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 15% of metamifop, 20% of composite emulsifier, 12% of cosolvent acetophenone, 0.75% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, and the balance of solvent naphtha S-150. Wherein the composite emulsifier is dodecyl benzene sulfonate, styryl phenol polyoxyethylene ether and isomeric tridecanol polyoxyethylene ether with the weight ratio of 1:4:8

To further illustrate the beneficial effects of the present invention, the related comparative example is set up by taking the metamifop emulsifiable concentrate of example 1 as an example only.

Comparative example 110% metamifop emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 20% of compound emulsifier, 10% of cosolvent acetophenone and the balance of solvent oil S-150. Wherein the composite emulsifier is dodecyl benzene sulfonate, styryl phenol polyoxyethylene ether and isomeric tridecanol polyoxyethylene ether with the weight ratio of 1:5:6

Comparative example 210% metamifop emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 20% of dodecyl benzene sulfonate, 10% of cosolvent acetophenone, 0.5% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, and the balance of solvent naphtha S-150.

Comparative example 310% metamifop emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 20% of styryl phenol polyoxyethylene ether, 10% of cosolvent acetophenone, 0.5% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, and the balance of solvent naphtha S-150.

Comparative example 410% metamifop emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 20% of isomeric tridecanol polyoxyethylene ether, 10% of cosolvent acetophenone, 0.5% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, and the balance of solvent naphtha S-150.

Comparative example 510% metamifop emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 5% of dodecyl benzene sulfonate, 10% of styryl phenol polyoxyethylene ether, 10% of cosolvent acetophenone, 0.5% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, and the balance of solvent naphtha S-150.

Comparative example 610% metamifop emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 6% of dodecyl benzene sulfonate, 15% of isomeric tridecanol polyoxyethylene ether, 10% of cosolvent acetophenone, 0.5% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, and the balance of solvent naphtha S-150.

Comparative example 710% Oxazolecarboxamide emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 6% of styryl phenol polyoxyethylene ether, 10% of isomeric tridecanol polyoxyethylene ether, 10% of cosolvent acetophenone, 0.5% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, and the balance of solvent naphtha S-150.

Comparative example 810% metamifop emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 20% of composite emulsifier, 10% of cosolvent acetophenone, 0.5% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide and solvent oil S-150 in balance. Wherein the weight ratio of the composite emulsifier to the dodecylbenzene sulfonate, the styryl phenol polyoxyethylene ether and the isomeric tridecanol polyoxyethylene ether is 2:1: 3.

Comparative example 910% metamifop emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 10% of cosolvent acetophenone, 0.5% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide, and the balance of solvent naphtha S-150.

Comparative example 1010% metamifop emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 20% of composite emulsifier, 0.5% of safener 2-methoxy-N- [ [4- [ [ (methylamino) carbonyl ] amino ] phenyl ] sulfonyl ] benzamide and solvent oil S-150. Wherein the composite emulsifier is dodecyl benzene sulfonate, styryl phenol polyoxyethylene ether and isomeric tridecanol polyoxyethylene ether with the weight ratio of 1:5:6

Comparative example 1110% Oxazolecarboxamide emulsifiable concentrate

The 10% metamifop emulsifiable concentrate comprises the following components in percentage by weight: 10% of metamifop, 20% of composite emulsifier, 10% of cosolvent acetophenone, 0.5% of safener isoxadifen, and the balance of solvent oil S-150. Wherein the weight ratio of the composite emulsifier to the dodecyl benzene sulfonate, the styryl phenol polyoxyethylene ether and the isomeric tridecanol polyoxyethylene ether is 1:5: 6.

2. Main performance index test of metamifop missible oil

The main performance index test of the metamifop emulsifiable concentrates of the examples 1-3 and the comparative examples 1-10 is determined, and the emulsion stability determination reference GB/T1603-2001 is a pesticide emulsion stability determination method; the cold and hot storage stability determination methods refer to a GB/T19136-2003 pesticide low-temperature stability determination method and a GB/T19136-2003 hot storage stability determination method respectively, and specific data are detailed in Table 1.

The detection method of the emulsion dispersibility comprises the following steps: slowly adding 1mL of emulsifiable solution into a beaker filled with hard water at a height of 2cm from the water surface by using an injector, and observing the emulsified and dispersed state;

determination standard of water-entering emulsification dispersion state:

first-stage: can be rapidly and automatically dispersed evenly, and is blue or pale transparent emulsion when being slightly stirred;

and (2) second stage: can automatically disperse in white cloud and form blue semitransparent emulsion by slight stirring;

third-stage: dispersing in silk form, and stirring to obtain blue opaque emulsion;

and (4) fourth stage: sinking in white microsphere shape, and stirring to obtain white opaque emulsion;

and (5) fifth stage: sinking in oil bead shape, emulsifying while stirring, and layering after stopping stirring.

TABLE 1

As can be seen from Table 1, the invention selects a reasonable component system, has good emulsification effect under the synergistic effect of the components, and all performance indexes are qualified.

3. Test of field efficacy and safety

Reagent to be tested: metamifop emulsifiable concentrates of examples 1-3 and comparative examples 1-11;

control target: barnyard grass and crab grass. Safety: rice (Oryza sativa L.) with improved resistance to stress

The test method comprises the following steps: the test was carried out in the field, with 3 replicates per group treatment, a treatment area of about 60m²And 3 leaves of the rice are in the 1-heart stage in the pesticide application period, the growth vigor is good, the plants are robust, and other plant diseases and insect pests do not exist. The medicine application method adopts a knapsack electric sprayer to carry out uniform spraying, and no heavy spraying and no leakage spraying are realized. The growth of rice was observed after 7 days of application, and the death of weeds was observed 15 days after application, and the herbicidal activities of the agents were compared. The results are shown in Table 2.

TABLE 2

As can be seen from Table 2, examples 1 to 3 (all with safeners added) of the present invention were safe to rice under the same conditions as the test, comparative example 1 showed dwarfing and yellowing of leaves of rice due to the absence of safeners, comparative example 11 showed that the safener isoxadifen was added, and also showed dwarfing and yellowing of leaves of rice. The weeding effects of the embodiments 1 to 3 of the invention on the crab grass and the barnyard grass are better than those of the comparative examples 2 to 10, and the invention has better popularization value.

While the foregoing is directed to the preferred embodiment of the present invention, it will be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention as defined in the appended claims.