A herbicidal composition containing metazachlor and fluthiacet-methyl

By combining pyrimisulfuron and flusulfanilamide, the problem of weed resistance was solved, achieving efficient and low-cost weed control, expanding the spectrum of weed control and ensuring rice safety.

CN117694357BActive Publication Date: 2026-07-14SHANGHAI ACAD OF AGRI SCI

Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
SHANGHAI ACAD OF AGRI SCI
Filing Date
2023-12-14
Publication Date
2026-07-14

AI Technical Summary

Technical Problem

In the existing technology, the long-term use of single or similar herbicide varieties has led to increasingly prominent problems of weed resistance, which poses a threat to rice production capacity, paddy field ecological security and rice quality safety.

Method used

A compound composition of two herbicides, pyrimisulfuron and flusulfanilamide, with an active ingredient ratio of (1-50):(1-50), is used to enhance the herbicidal effect, broaden the weed control spectrum, reduce the cost of pesticide application, and delay resistance development through synergistic effects of different mechanisms of action.

Benefits of technology

It significantly enhances weed control, broadens the weed-killing spectrum, reduces pesticide costs, minimizes the impact on the ecological environment, extends the pesticide's lifespan, and ensures safety for rice.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present application relates to the technical field of agricultural weeding, and particularly relates to a weeding composition containing metazachlor and dithiopyr. Active ingredients of the weeding composition include metazachlor and dithiopyr; the mass ratio of the metazachlor and the dithiopyr is (1-50):(1-50). The present application can effectively reduce the application amount of each single agent (metazachlor or dithiopyr) by compounding metazachlor and dithiopyr as effective ingredients of the weeding composition, has a synergistic effect; the weeding composition has a long weeding persistence, reduces the number of application times, and delays the drug resistance of weeds; the weeding composition can expand the weed spectrum, has a significant prevention effect on various broadleaf weeds, sedge and gramineous weeds; and the weeding composition is safe for rice growth.
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Description

Technical Field

[0001] This invention relates to the field of agricultural weed control technology, and in particular to a weed control composition containing pyrimisulfuron and flufenoxuron. Background Technology

[0002] Rice is one of the most important food crops and a crucial foundation for ensuring food security. Weeds are a significant factor affecting rice yield and quality. Currently, chemical control is the most convenient and effective method for controlling weeds in paddy fields. However, due to the long-term use of single or similar herbicides, weed resistance has become increasingly prominent, posing a serious threat to the improvement of rice production capacity, paddy field ecological security, and rice quality safety. Summary of the Invention

[0003] Based on the above, this invention provides a herbicidal composition containing pyrimisulfuron and flufenoxuron. This composition exhibits significant synergistic effects, excellent herbicidal efficacy, a broadened weed control spectrum, low application cost, and the advantages of delaying weed resistance development and being safe for rice.

[0004] To achieve the above objectives, the present invention provides the following solution:

[0005] One of the technical solutions of the present invention is a herbicidal composition containing pyrimisulfuron and flusulfuron, wherein the active ingredients include pyrimisulfuron and flusulfuron;

[0006] The mass ratio of pyrazosulfuron to flusulfuron is (1-50):(1-50).

[0007] The second technical solution of the present invention is the application of the above-mentioned herbicidal composition containing pyrimisulfuron and flufenoxuron in the control of weeds in paddy fields.

[0008] The present invention discloses the following technical effects:

[0009] The herbicidal composition provided by this invention has a significant synergistic effect, which can reduce the dosage of pesticides, reduce the cost of pesticide use, and reduce the adverse effects of pesticides on the ecological environment.

[0010] The herbicidal composition provided by this invention expands the spectrum of weed control, and can solve the problem of various weeds, including annual and perennial weeds, with a single application, making up for the defects and limitations of single-agent use, and has good safety for rice.

[0011] The herbicidal composition provided by this invention has two active ingredients with different mechanisms of action, which can overcome the disadvantage of resistance easily generated by long-term single use, extend the service life of the herbicide, and is of great significance for the integrated management of weed resistance. Detailed Implementation

[0012] Various exemplary embodiments of the present invention will now be described in detail. This detailed description should not be considered as a limitation of the present invention, but rather as a more detailed description of certain aspects, features, and embodiments of the present invention.

[0013] It should be understood that the terminology used in this invention is merely for describing particular embodiments and is not intended to limit the invention. Furthermore, with respect to numerical ranges in this invention, it should be understood that each intermediate value between the upper and lower limits of the range is also specifically disclosed. Any stated value or intermediate value within a stated range, as well as each smaller range between any other stated value or intermediate value within said range, is also included in this invention. The upper and lower limits of these smaller ranges may be independently included or excluded from the range.

[0014] Unless otherwise stated, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. While only preferred methods and materials have been described herein, any methods and materials similar or equivalent to those described herein may be used in the implementation or testing of this invention. All references to this specification are incorporated by way of citation to disclose and describe methods and / or materials associated with those references. In the event of any conflict with any incorporated reference, the content of this specification shall prevail.

[0015] Various modifications and variations can be made to the specific embodiments described in this specification without departing from the scope or spirit of the invention, as will be apparent to those skilled in the art. Other embodiments derived from this specification will also be apparent to those skilled in the art. This specification and embodiments are merely exemplary.

[0016] The terms “include,” “including,” “have,” “contain,” etc., used in this article are all open-ended terms, meaning that they include but are not limited to.

[0017] The first aspect of the present invention provides a herbicidal composition containing pyrimisulfuron and flusulfuron, wherein the active ingredients include pyrimisulfuron and flusulfuron;

[0018] The mass ratio of pyrazosulfuron to flusulfuron is (1-50):(1-50). In a preferred embodiment of the present invention, the mass ratio of pyrazosulfuron to flusulfuron is (1-30):(1-30); in a further preferred embodiment of the present invention, the mass ratio of pyrazosulfuron to flusulfuron is (1-20):(1-20); in the most preferred embodiment of the present invention, the mass ratio of pyrazosulfuron to flusulfuron is 1:2.

[0019] Using a single herbicide in paddy fields is insufficient to effectively control weeds. Excessive application can also cause residual toxicity to current or subsequent crops. Properly combining or mixing herbicides is an effective method to improve control efficacy, broaden the weed control spectrum, reduce dosage, mitigate environmental pollution, extend the optimal application period, delay the development of weed resistance, lower costs, and reduce herbicide residues.

[0020] Pyrimisulfuron is an acetolactate synthase inhibitor herbicide that inhibits the biosynthesis of key amino acids (valine, leucine, and isoleucine), thereby hindering cell division, suppressing plant growth, and ultimately causing weed death. Pyrimisulfuron is characterized by low toxicity, high activity, and high selectivity, and is mainly used to control weeds such as velvetleaf, amaranth, barnyard grass, and privet in rice and wheat fields. Pyrimisulfuron also has good control effects on sulfonylurea-resistant weeds, such as resistant species like *Impatiens balsamina*, *Symplocos edulis*, *Heliotropium indicum*, *Monochoria vaginalis*, *Alisma plantago-aquatica*, and *Sagittaria sagittifolia*.

[0021] Fluthion is a pyridine carboxylic acid herbicide that kills weeds by inhibiting cell division through disrupting the formation of microtubules in the weed spindle apparatus. Fluthion is effective against annual weeds such as barnyard grass, duckweed, sedge, jointed grass, and narrow-leaved water plantain, but its effectiveness against weeds such as fireweed, water sedge, water sedge, and arrowhead is poor.

[0022] This invention uses a combination of pyrimisulfuron and flusulfuron as the active ingredient in a herbicidal composition, which can effectively reduce the application rate of each single agent (pyrimisulfuron or flusulfuron) and has a synergistic effect. The herbicidal composition has a long-lasting herbicidal effect, reduces the number of applications, and delays the development of herbicide resistance in weeds. The herbicidal composition can broaden the spectrum of weed control and has significant control effects on a variety of broadleaf weeds, sedges, and grass weeds. The herbicidal composition is safe for rice growth.

[0023] In a preferred embodiment of the present invention, the active ingredient accounts for 10-80% of the mass of the herbicidal composition containing pyrimisulfuron and flufenoxuron.

[0024] In a preferred embodiment of the present invention, the active ingredient accounts for 20-60% of the mass of the herbicidal composition containing pyrimisulfuron and flusulfanilamide.

[0025] In a preferred embodiment of the present invention, the active ingredient and excipients can be formulated into any dosage form permitted in agriculture.

[0026] Excipients include: solvents, cosolvents, dispersants, wetting agents, disintegrants, emulsifiers, antifreeze agents, defoamers, thickeners, fillers, deionized water, preservatives, etc. The selection of excipients consists of commonly used or permitted components in pesticide formulations, without specific limitations.

[0027] In a preferred embodiment of the present invention, the dosage form is a dispersible oil suspension, an emulsifiable concentrate, or a wettable powder.

[0028] A second aspect of this invention provides the application of the above-mentioned herbicidal composition containing pyrimisulfuron and flufenoxuron in the control of weeds in paddy fields. It is mainly used in transplanted rice fields to control annual and perennial weeds.

[0029] In a preferred embodiment of the present invention, the weeds are barnyard grass, water amaranth, sedge, and / or flat-stemmed sedge.

[0030] Unless otherwise specified, the "%" mentioned in this invention refers to a percentage by mass.

[0031] Unless otherwise specified, all raw materials used in the embodiments of this invention can be obtained through commercial channels.

[0032] The methylated vegetable oil used in this embodiment of the invention is specifically methylated soybean oil (soybean oil methyl ester), with a density of 0.87-0.89 g / cm³. 3 The content is 98%, and the acid value is ≤2. (Other methylated vegetable oils such as methylated cottonseed oil, corn oil, sunflower oil, peanut oil, flaxseed oil, and castor oil are also applicable to this invention).

[0033] Example 1

[0034] 30% Pyrimisulfuron·Fluthiocyanate EC: By weight percentage, it consists of 10% pyrimisulfuron, 20% fluthiocyanate, 6.5% phenylethylphenol polyoxyethylene polyoxypropylene ether, 3.5% calcium dodecylbenzenesulfonate, and the balance being methylated vegetable oil.

[0035] Mix the above raw materials and stir until a transparent and homogeneous phase is obtained, which yields a 30% mass fraction of pyrimisulfuron-fluthiosulfate emulsifiable concentrate.

[0036] Example 2

[0037] 30% Pyrimisulfuron-Fluthiocyanate Dispersible Oil Suspension: By mass percentage, it consists of 10% pyrimisulfuron, 20% fluthiocyanate, 5% polyoxyethylene stearate, 4% tristyrylphenol polyoxyethylene polyoxypropylene ether, 7% alkylphenol formaldehyde resin polyoxyethylene ether, 4% bentonite, and the balance soybean oil.

[0038] Mix the above raw materials evenly and grind them in a sand mill to obtain a 30% by mass dispersible oil suspension of pyrimisulfuron-fluthiosulfate.

[0039] Example 3

[0040] 30% Pyrimisulfuron-Fluthion Wettable Powder: By mass percentage, it consists of 10% pyrimisulfuron, 20% fluthion, 2% sodium lignosulfonate, 5% naphthalenesulfonate dispersant, 10% ammonium sulfate, 6% silica, and the balance kaolin.

[0041] The above raw materials are added together in a conical mixer and mixed evenly, and then pulverized by an air jet mill to obtain a 30% wettable powder of pyrimisulfuron-fluthoxam.

[0042] Example 1 of effect verification

[0043] Toxicity assay of different ratios of pyrimisulfuron and flusulfanilamide

[0044] 1. Test conditions

[0045] 1.1 Test Target

[0046] The seeds of barnyard grass, water amaranth, and sedge were collected from rice paddies.

[0047] Pot cultivation was used. 140×140mm plastic seedling pots were placed in trays filled with topsoil collected from farmland, dried, and sieved. Water was added directly to the top of the pots to maintain initial soil saturation. Plump and uniform weed seeds were selected and germinated in a 25 / 30℃ (dark) incubator. The newly sprouted weed seeds were then evenly distributed on the soil surface, covered with 0.5cm of soil, and kept fully moist after sowing. The pots were then placed in a controlled-light greenhouse for cultivation.

[0048] 1.2 Cultivation Conditions

[0049] The experiment was conducted in a controlled-temperature greenhouse with nighttime temperatures of 20–25°C and daytime temperatures of 25–30°C, under natural light and relative humidity of 60–75%. The soil type was loam, with an organic matter content of 1.8% and a pH of 7.1.

[0050] 1.3 Instruments and Equipment

[0051] ASS-4 automatic quantitative spraying system, GA110 electronic balance with a ratio of 0.01%; ZDR2000 intelligent data logger, MLR-352H plant incubator.

[0052] 2. Experimental Design

[0053] 2.1 Test reagents

[0054] The technical grade pesticides are 91% (w / w) pyrazosulfuron and 95% (w / w) flusulfanilamide. Both technical grade pesticides are dissolved in acetone and diluted with a 0.1% Tween 80 emulsifier aqueous solution, diluted immediately before use.

[0055] 2.2 Test Treatment

[0056] 2.2.1 Dosage setting

[0057] Based on the respective activities and laboratory assay characteristics of the two agents, different mixing combinations were designed according to the initial laboratory assays, as shown in Tables 1, 2, and 3, for a total of 9 groups. Water containing the same emulsifier but without the agent was used as a blank control for laboratory bioassays.

[0058] 2.2.2 Experimental Repetition

[0059] Each treatment was repeated 4 times, with 3 pots per treatment each time. 20 weed seeds were sown in each pot, for a total of 60 plants per treatment.

[0060] 3. Handling Method

[0061] 3.1 Processing time and number of times

[0062] The experiment used the same pesticide once. When barnyard grass reached the 2-leaf-1-heart stage, water amaranth reached the 2-true-leaf stage, and sedge reached the 2-leaf stage, thinning was carried out to maintain 15 weeds per pot, and 45 weeds were retained for each treatment.

[0063] 3.2 Use of instruments and methods of medication

[0064] Arrange the weeds evenly on the platform and spray using the ASS-4 automatic metered spraying system with a TeeJet XR 8002VS fan-shaped nozzle at a flow rate of 450 L / ha and a spraying pressure of 0.275 MPa. After 30 seconds of spraying, open the spray tower door and remove the nutrient pots. Then, open the air valve and spray 100 ml of clean water to clean the spray pipes.

[0065] 4. Test methods

[0066] The test was conducted in accordance with the "Guidelines for Indoor Bioassay Testing of Pesticides" -- NY / T1155.9-2008 and NY / T1155.7-2006.

[0067] 5. Data Survey and Statistical Analysis

[0068] 5.1 Survey Methodology

[0069] Because the concentration gradients in the experiment were inconsistent, weeds at low concentrations did not die completely. Therefore, the absolute number method was used to investigate the fresh weight of the weeds. Surviving weed seedlings were cut along the soil surface with scissors, and the fresh weight of the weeds was measured using an analytical balance.

[0070] 5.2 Survey Time and Frequency

[0071] An investigation was conducted 15 days after the incident, for a total of one investigation.

[0072] 5.3 Data Statistical Analysis

[0073] According to survey statistics, the formula for calculating the fresh weight inhibition rate is as follows:

[0074] Fresh weight inhibition rate (%) = (Control fresh weight - Treatment fresh weight) / Control fresh weight × 100

[0075] The theoretical fresh weight inhibition rate (E0) for each treatment combination was calculated using the Gowing method, and the formula is as follows:

[0076] E0(%)=X+YX×Y / 100

[0077] In the formula, X is the fresh weight inhibition rate of target weeds when pyrimisulfuron is used alone at a certain dose; Y is the fresh weight inhibition rate of target weeds when fluthioprazole is used alone at a certain dose; E0 is the theoretical value of the fresh weight inhibition rate of target weeds when pyrimisulfuron and fluthioprazole are used in combination; and E is the measured value of the fresh weight inhibition rate of target weeds when pyrimisulfuron and fluthioprazole are used in combination.

[0078] The combined effects of the two herbicides on weeds were evaluated. An E-E0 value greater than 10% indicated a synergistic effect, less than -10% indicated an antagonistic effect, and between -10% and 10% indicated an additive effect. The optimal ratio was determined based on actual control efficacy, herbicide characteristics, and the balance of the formulation.

[0079] Table 1. Combined effects of pyrimisulfuron-methyl and flusulfanilamide on barnyardgrass (Gowing method)

[0080]

[0081]

[0082] Table 2. Combined effects of pyrimisulfuron-methyl and flusulfanilamide on amaranth (Gowing method)

[0083]

[0084] Table 3. Combined effects of pyrimisulfuron-methyl and flusulfanilamide on Cyperus difformis (Gowing method)

[0085]

[0086]

[0087] 6. Results Analysis

[0088] The experimental results in Tables 1, 2, and 3 show that the herbicidal composition of the present invention has excellent control effects on barnyard grass, amaranth, and sedge, with significant synergistic effects among the active ingredients. The results also show that, without considering dosage, the higher the dosage of pyrazosulfuron + fluoxetine, the better the effect. Conversely, from the perspective of saving costs and reducing raw material usage, the optimal dosage ratio of pyrazosulfuron + fluoxetine is 1:2, i.e., 15 + 30 g ai / ha, which provides the best control effect, with the actual fresh weight inhibition rate of weeds exceeding 95%. (Note: The recommended field dosage of fluoxetine is 60–120 g ai / ha, and the recommended field dosage of pyrazosulfuron is also 60–120 g ai / ha. Therefore, the present invention strictly controls the dosage of both to meet the requirements.)

[0089] Example 2 of effect verification

[0090] Field efficacy test of herbicide composition for controlling weeds in transplanted rice fields

[0091] 1. Test reagents: Formulation of Example 1 (30% pyrimisulfuron-fluthiocyanate emulsifiable concentrate), formulation of Example 2 (30% pyrimisulfuron-fluthiocyanate dispersible oil suspension), formulation of Example 3 (30% pyrimisulfuron-fluthiocyanate wettable powder), and control reagents (33% pyrimisulfuron-fluthiocyanate water dispersible granules and 32% fluthiocyanate emulsifiable concentrate).

[0092] 2. The experimental crop was rice, and the target weeds were annual grasses, broadleaf weeds, and sedges in rice paddies: barnyard grass, water amaranth, and sedge of different species, as well as perennial weeds such as flat-stemmed sedge.

[0093] 3. Experimental Methods: The experiment included 5 herbicide treatments and a blank control, for a total of 6 treatments. The plot area was 20m². 2 The experimental plots were randomly assigned to blocks, with protective rows around the perimeter. Each plot could be irrigated individually. Each treatment was replicated four times. The pesticide was applied 7 days after rice transplanting. The application method was the soil application method. After application, a 3-5 cm water layer was maintained in the paddy field for 5-7 days, ensuring that the water layer did not submerge the rice whorls.

[0094] The weed control efficacy of each treatment was assessed at 21 and 42 days post-application. The survey method involved surveying four points per plot, each 0.25 m wide. 2 The formula for calculating drug efficacy is as follows:

[0095] Control efficacy (%) = (CK - PT) / CK × 100

[0096] In the formula: CK is the number of weeds in the blank control area, and PT is the number of residual weeds in the treated area.

[0097] Table 4. Field efficacy of herbicides for controlling weeds in rice paddies (21 days after application).

[0098]

[0099] Table 5. Field efficacy of herbicides for controlling weeds in rice paddies (42 days after application).

[0100]

[0101] 4. Results Analysis:

[0102] Field trial results showed that when the application rate of 30% pyrimisulfuron-fluthiocyanate EC, 30% pyrimisulfuron-fluthiocyanate SC, and 30% pyrimisulfuron-fluthiocyanate WP was 90 g ai / ha, they all had good control effects on barnyard grass, amaranth, sedge, and flat-stemmed sedge in paddy fields. The overall control efficacy at 21 days and 42 days after application was significantly better than that of single-agent 33% pyrimisulfuron-fluthiocyanate granules at 99 g ai / ha and 32% fluthiocyanate EC at 90 g ai / ha (Tables 4 and 5).

[0103] Safety investigation: The safety of each treatment on rice seedlings was visually assessed at 7, 14, and 21 days after application. The results showed that all tested pesticides were safe for rice growth, and no phytotoxicity phenomena such as chlorosis or dwarfing occurred.

[0104] In summary, the herbicidal composition of the present invention employs a combination of two active ingredients. Its activity and herbicidal effect are not simply the sum of the activities of each component. Compared with existing single formulations, it has a significant synergistic effect, good safety, and meets the requirements of pesticide reduction development.

[0105] The embodiments described above are merely preferred embodiments of the present invention and are not intended to limit the scope of the present invention. Various modifications and improvements made by those skilled in the art to the technical solutions of the present invention without departing from the spirit of the present invention should fall within the protection scope defined by the claims of the present invention.

Claims

1. The application of a herbicidal composition containing pyrimisulfuron and flufenoxuron in the control of weeds in paddy fields, characterized in that, The weeds in the paddy field are water amaranth and / or flat-stemmed bulrush; the active ingredients of the herbicidal composition include pyrimisulfuron and flufenoxuron; The mass ratio of pyrimisulfuron-methyl to flusulfuron-methyl is 1:

2.

2. The application of the herbicidal composition containing pyrimisulfuron and flufenoxuron according to claim 1 in the control of weeds in paddy fields, characterized in that, The active ingredient comprises 10-80% of the mass of the herbicidal composition containing pyrimisulfuron and flufenoxuron.

3. The application of the herbicidal composition containing pyrimisulfuron and flufenoxuron according to claim 1 in the control of weeds in paddy fields, characterized in that, The active ingredient comprises 20-60% of the mass of the herbicidal composition containing pyrimisulfuron and flufenoxuron.

4. The application of the herbicidal composition containing pyrimisulfuron and flufenoxuron according to claim 1 in the control of weeds in paddy fields, characterized in that, The active ingredients and excipients can be formulated into any dosage form permitted in agriculture.

5. The application of the herbicidal composition containing pyrimisulfuron and flufenoxuron according to claim 4 in the control of weeds in paddy fields, characterized in that, The dosage form is a dispersible oil suspension, emulsifiable concentrate, or wettable powder.