TWI811594B - Herbicidal composition - Google Patents

Abstract

The present invention relates to a herbicidal composition comprising pyribenzoxim (PBX), penoxsulam (PNS), an organic solvent, and an emulsifier, wherein the organic solvent is gamma-butyrolactone (GBL).

Description

Herbicide composition

The present invention relates to a herbicide composition. Cross-reference related applications

This application claims rights in Korean Patent Application No. 10-2019-0173212 filed with the Korean Intellectual Property Office on December 23, 2019, the disclosure of which is incorporated herein by reference in its entirety.

In crop cultivation technology, it is important to protect crops by controlling weeds that inhibit crop growth. In order to reduce damage caused by weeds in crop cultivation, such as crop growth retardation or yield reduction, herbicidal active substances that are effective in controlling weeds and are safe for crops have been developed. Many of the herbicides developed to date have been registered for use in specific crops and for weed control. Herbicides used to control weed growth in areas where this particular crop is grown are preferably ones that have high herbicidal activity and broad range of herbicidal effects, but are safe for the environment and the crop. However, not all herbicides meet these conditions perfectly.

The most common method for increasing the herbicidal activity and broad-spectrum herbicidal effect of existing herbicides is to mix two or more herbicidal active substances with different herbicidal activities. When two or more herbicidal active substances are mixed, the herbicidal effect may be more excellent than when these herbicides are used to treat weeds individually (single-agent treatment). A "synergistic effect" occurs when the efficacy or activity exhibited is equal to or greater than would be predicted from the results of the individual efficacy of the components. However, when two or more herbicidal active substances are mixed, the synergistic effect of herbicides only occurs in some cases. On the contrary, due to the differences in herbicidal properties, absorption, transformation, metabolism, etc. of the two herbicides, in many cases it is Herbicidal activity is lower than that of single agent treatment. Thus, the situation in which two herbicidal active substances are less effective at weeding when mixed is called "antagonism." In addition, the situation where there is no change in herbicidal efficacy when mixing herbicidal active substances is called "additive effect".

Pyribenzoxim (PBX) is a herbicide used from germination to post-emergence. It has the effect of inhibiting the activity of acetolactate synthase (ALS). Due to the strong absorption capacity of the soil, PBX is mainly used for the treatment of stems and leaves. Traditionally, PBX has been mainly developed as a single agent; however, due to the emergence of resistant weeds and to expand the broad range of herbicidal effects, research is being conducted on the development of mixtures. Among them, PBX ) in combination with other herbicidal active substances. At the same time, a variety of PBX formulations (WP, WG, OD, SC, etc.) have been studied, but in the emulsifiable concentrate (EC) formulation containing a large amount of specific emulsifiers Shows optimal effectiveness. However, because PBX requires a large amount of emulsifier to exhibit sufficient efficacy, the amount of solvent used is limited. Therefore, naphtha-based organic solvents commonly used in blend development have difficulty ensuring formulation stability.

Therefore, there is a need to develop a herbicide composition as a mixture with PBX that exhibits excellent herbicidal activity due to the synergistic effect with PBX and is emulsifiable. Excellent formulation stability in concentrate (EC) formulations.

[Prior Technical Document]

[Patent document]

China Patent Application Publication No. 104186503

technical issues

One aspect of the present invention provides a herbicide composition of an emulsifiable concentrate (EC) formulation, which is a mixture containing pyrimidinate and pyrimidinate (PBX), which not only has a synergistic effect with pyrimidinate and pyrimidine It uses specific herbicidal active substances to exhibit excellent herbicidal activity and also has excellent formula stability. Technical solutions

The present invention provides a herbicide composition, which contains pyrimidine fenoxifen (PBX), penoxsulam (PNS), an organic solvent, and an emulsifier, wherein the organic solvent is γ-butyrolactone (GBL). beneficial effects

According to the present invention, a herbicide composition of an emulsifiable concentrate (EC) formula can be provided, which is in the form of a mixture containing pyrimidinate (PBX) and pyrimidine (PNS), exhibits excellent herbicidal activity and has Excellent properties of immediate release and sustained release as well as excellent formula stability.

The present invention will be described in more detail below to facilitate a clearer understanding of the invention. It will be understood that words or terms used in the specification and claims should not be construed according to commonly used dictionary definitions. It will be further understood that in accordance with the principle that the inventor can appropriately define the meaning of words or terms to best explain the invention, words or terms should be interpreted to have a meaning consistent with the meaning in the context of the relevant technology and the technical idea of the invention.

The present invention provides a herbicide composition, which contains pyrimidine trifluorfen (PBX), pyrizofen (PNS), an organic solvent, and an emulsifier, wherein the organic solvent is γ-butyrolactone (GBL).

Pyrimidinoximefen (PBX) is a herbicide used from germination to post-emergence. It has the effect of inhibiting the activity of acetyl lactic acid synthase (ALS). Because PBX has strong soil absorption properties, it is mainly used for the treatment of stems and leaves. Traditionally, PBX has been mainly developed as a single agent; however, due to the recent emergence of resistant weeds and limitations in broad-spectrum herbicidal effects, there is a need to develop mixtures of PBX with other herbicidal active substances. Mixture. Therefore, the present invention developed a mixture of pyrimidine pyrimidinate (PBX) and plain sodium chloride (PNS). PNS can be absorbed through leaves and roots, and can be used on weeds from germination to post-emergence and before weeds emerge. In addition, PNS has a wide range of control effects such as grasses, broadleaf weeds, sedges, etc. The mixture of pyrimidinate (PBX) and pyrimidine (PNS) has the excellent characteristics of immediate release and sustained release, has a wide range of herbicidal control, and has excellent herbicidal activity.

At the same time, mixtures of pyrimidine pyrimidinate (PBX) and sulfate (PNS) have been studied in various formulations (WP, WG, OD, SC, etc.), but in emulsifiable concentrates (EC) containing a large amount of specific emulsifiers ) formula shows optimal effectiveness. However, in the case of emulsifiable concentrates (EC), a large amount of emulsifier is required to exhibit sufficient effectiveness, and therefore, the amount of solvent used is limited. In the case of naphtha-based or aromatic-based organic solvents commonly used in emulsifiable concentrate (EC) formulations, there is a problem of difficulty in ensuring formulation stability. In addition, since neither PBX nor PNS has high solubility in traditional organic solvents, it is difficult to develop emulsifiable concentrate (EC) formulations. In this regard, in the present invention, by using γ-butyrolactone (GBL) as an organic solvent, a herbicide composition of a mixture of pyrimidine trifenfenate (PBX) and pyrimidine (PNS) was developed, It has increased solubility and excellent formulation stability.

According to embodiments of the present invention, relative to 100 parts by weight of the herbicide composition, the content of pyrimidine cyclofenac (PBX) may be 0.1-10.0 parts by weight, more preferably 1.0-5.0 parts by weight, and even more preferably 2.5 -3.0 parts by weight. In addition, according to embodiments of the present invention, relative to 100 parts by weight of the herbicide composition, the content of PNS may be 0.1-10.0 parts by weight, more preferably 1.0-5.0 parts by weight, and even more preferably 1.5-2.0 parts by weight. Optimally, relative to 100 parts by weight of the herbicide composition, the content of pyrimidine trifluorfen (PBX) can be 2.5-3.0 parts by weight and the content of plain rotten (PNS) can be 1.5-2.0 parts by weight. In addition, the weight ratio of PBX and PNS can be 1:0.1 to 1:3.0, and a more preferable weight ratio is 1:0.2 to 1:1.0, and even better. is 1:0.5 to 1:0.8. By containing pyrimidine trifluorfen (PBX) and pyrimidine (PNS) within the above weight range, the herbicide composition can have a synergistic effect, thereby exhibiting excellent herbicidal activity and excellent characteristics of immediate release and sustained release.

At the same time, the herbicide composition of the present invention can be an emulsifiable concentrate (EC) formulation containing an organic solvent and an emulsifier, and excellent medicinal efficacy can be ensured by forming the composition with an emulsifiable concentrate (EC) formulation. . However, in the case of emulsifiable concentrate (EC) formulations, the problem is that the solubility of pyrimidine pyrimidine (PBX) and sulfamethoxazole (PNS) is not high, making it difficult to ensure formulation stability. On the contrary, by containing γ-butyrolactone (GBL) as an organic solvent, the herbicide composition of the present invention is very soluble and can ensure excellent formulation stability. Relative to 100 parts by weight of the herbicide composition, the content of γ-butyrolactone (GBL) may be 50-70 parts by weight, more preferably 60-68 parts by weight, and even more preferably 64-66 parts by weight. By containing gamma-butyrolactone (GBL) within the above weight range, the effect of preventing low-temperature precipitation of the original agent can be provided.

The emulsifier included in the herbicide composition of the present invention may be at least one or more selected from the group consisting of anionic emulsifiers, nonionic emulsifiers, or cationic emulsifiers, and in particular, at least one or more selected from the group consisting of Alkyl aryl ether sulfates, phosphate ester salts, sulfosuccinates, alcohol ether ethoxylates, alcohol ether alkoxylates, alkylphenol ether ethoxylates, alkylphenol ether alkoxylates, Block copolymers, fatty acid alkoxylates, fatty amine alkoxylates, alkyl polyglucosides, alkoxylated vegetable oils, sorbitol ester alkoxylates, amine oxides, fatty amine alkoxylates, or The group consisting of quaternary ammonium salts, and more preferably, may include polyoxyethylene lauryl ether and polyethylene-polypropylene copolymer as emulsifiers. The emulsifier makes the droplet size of the emulsion nanoscale, thus maximizing the penetration of PBX into the leaf surface. The content of the emulsifier may be 15-45 parts by weight, preferably 25-35 parts by weight, relative to 100 parts by weight of the herbicide composition. By containing the emulsifier within the above weight range, it has the effect of maximizing the penetration of PNS into the leaf surface.

The following examples are provided for illustrative purposes only to illustrate to those skilled in the art how the provided compounds, compositions, and methods may be made and evaluated. Therefore, these examples are not intended to limit the scope of what the inventors believe to be the invention. There are many variations and combinations of reaction conditions. For example, conditions such as ingredient concentration, desired solvent, solvent mixture, temperature, pressure, and other reaction parameters, as well as purity, yield, etc., can be used to optimize product performance. These are also considered to be included in the scope of this case. Any combination of the above-described elements in all possible variations is encompassed by the invention unless otherwise indicated herein or unless otherwise clearly contradicted by context.

[Experimental Example 1: Evaluation of formula stability]

Mix 3 g of pyrimidine trifluorfen (PBX) and 2 g of pyrimidine (PNS) with 65 g of the solvent according to Table 1 respectively. Stir the mixture at 50°C with a stirrer at a speed of 400 rpm and check the dissolution state of the mixture. Afterwards, the dissolution stability was evaluated by storing the mixture at low temperature (0°C) for 2 weeks and checking whether the original agent precipitated.

[ Table 1] Solvent Dissolution of the original potion Precipitation of the original potion (store for 2 weeks) K-200S (solvent naphtha, heavy aromatic compounds) X O K-150 (solvent naphtha, heavy aromatic compounds) X O K-100 (solvent naphtha, light aromatic compounds) X O CR-MO (methyl oleate) X O AG-1555 (propylene carbonate) X O AG-1730 (morphinamide, C8-C10 fatty acid) X O cottonseed oil X O castor oil X O NMP (N-methylpyrrolidone) O O NOP (N-Octylpyrrolidone) X O Exxsol D-100 (hydrocarbon, C12-C15, linear alkanes) X O Exxsol D-130 (distillate oil (petroleum), hydrotreated medium oil) X O AMD810 (C8-C10 fatty acid dimethylamide) X O xylene X O GBL (γ-butyrolactone) O X

Referring to Table 1, in various solvents, NMP and γ-butyrolactone (GBL) dissolve the original pharmaceutical, but when stored at low temperature, NMP precipitates. γ-Butyrolactone (GBL) not only fully dissolves the original agent, but also does not precipitate during low-temperature storage, thus showing excellent solution stability.

Example 1

Mix 3 g of pyrimidinoximefen (PBX) and 2 g of pyrimidine (PNS) with 65 g of γ-butyrolactone (GBL), and stir the mixture at 50°C with a stirrer at a speed of 400 rpm to dissolve the mixture. After visually confirming that the mixture has dissolved, stop heating. Next, a total amount of 30 g of polyoxyethylene lauryl ether and polyethylene-polypropylene copolymer as emulsifiers was added and fully stirred with a stirrer at a speed of 400 rpm to prepare an emulsifiable concentrate (EC) herbicide. composition.

Comparative example 1

A single dose (Pyribenzoxim, PBX) was prepared as an emulsifiable concentrate (EC) formulation containing 5 g of pyribenzoxifen (PBX) (product name: Pyanchor). In addition, a single dose of PNS in the form of a suspension concentrate (SC) containing 3 g of PNS was prepared (product name: Salchodaechub). Mix PBX single agent and PNS single agent immediately before handling and use.

Comparative example 2

A herbicide composition (product name: Pyanchor gold) formulated as an emulsifiable concentrate (EC) was used, which contained 6 g of cyhalofop butyl (CHF) and 2.5 g of pyrimidine pyrimidine (PBX).

Comparative example 3

Use an oil-phase concentrate (OD) herbicide composition (product name: Topshot), which contains 5 g butyl sefer grass (CHF) and 1 g flat speed rot (PNS).

[Experimental Example 2: Evaluation of drug efficacy]

Herbicide efficacy was evaluated using the herbicide compositions of Example 1 and Comparative Examples 1 to 3. Specifically, the target weeds used were rice cockspur (resistant and sensitive), Leptochloa chinensis , Cyperus difformis , and Ludwigia prostrata . When treated, the growth stage of weeds is approximately the 4-leaf stage, and pre-emergence is two days after weed sowing. When diluting the product, the amount of water used is based on 300 L/ha, and herbicidal activity is visually observed on days 8, 14, and 26 after chemical treatment. Before and after treatment, handle the stems and leaves to manage the pots after complete drainage, and maintain a water depth of 1 cm for 24 hours after treatment.

The results are shown in Table 2 below.

Referring to Table 2 above, the herbicidal activity of the herbicide composition according to Example 1 is better than that of Comparative Example 1. In addition, the herbicidal activity of the herbicide composition according to Example 1 against Cyperus difformis (resistant), Cyperus difformis (sensitive ) , and Ludwigia prostrata was compared. Examples 2 and 3 were shown to be faster and better in comparison, however, the herbicidal activity of the herbicide composition according to Example 1 against Leptochloa chinensis was shown to be slightly worse.

Claims (8)

A herbicide composition in the form of an emulsifiable concentrate (EC) formulation, which includes pyribenzoxim (PBX), penoxsulam (PNS), an organic solvent, and an emulsifier , wherein the organic solvent is γ-butyrolactone (GBL), and the content of γ-butyrolactone (GBL) is 64-66 parts by weight relative to 100 parts by weight of the herbicide composition. For example, the herbicide composition of claim 1, wherein the content of pyrimidinate (PBX) is 0.1-10 parts by weight relative to 100 parts by weight of the herbicide composition. For example, the herbicide composition of claim 1, wherein the content of PNS is 0.1-10 parts by weight relative to 100 parts by weight of the herbicide composition. For example, the herbicide composition of claim 1 contains pyrimidinate (PBX) and pyrimidine (PNS) in a weight ratio of 1:0.1 to 1:3.0. For example, the herbicide composition of claim 1, wherein relative to 100 parts by weight of the herbicide composition, the content of pyrimidine pyrimidine (PBX) is 2.5-3.0 parts by weight, and the content of PNS (PNS) is 1.5 -2.0 parts by weight. The herbicide composition of claim 1, wherein the emulsifier is at least one or more selected from the group consisting of alkyl aryl ether sulfates, phosphate ester salts, sulfosuccinates, alcohol ether alkoxylates, and alkyl phenol ethers. Alkoxylates, block copolymers, fatty acid alkoxylates, fatty amine alkoxylates, alkyl polyglucosides, alkoxylated vegetable oils, sorbitol ester alkoxylates, A group consisting of amine oxides and quaternary ammonium salts. The herbicide composition of claim 1, wherein the emulsifier includes polyoxyethylene lauryl ether and polyethylene-polypropylene copolymer. The herbicide composition of claim 1, wherein the content of the emulsifier is 15-45 parts by weight relative to 100 parts by weight of the herbicide composition.