WO2021132941A1 - Herbicide composition - Google Patents

Abstract

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

Description

Herbicide composition

Cross Citation with Related Applications

This application claims the benefit of priority based on Korean Patent Application No. 10-2019-0173212 dated December 23, 2019, and all contents disclosed in the literature of the Korean patent application are incorporated as a part of this specification.

technical field

The present invention relates to a herbicide composition.

In crop cultivation technology, it is important to protect crops by controlling weeds that inhibit the growth of crops. In order to reduce damage such as poor growth of crops or decrease in yield due to weeds generated in crop cultivation areas, herbicidal active substances that can effectively control them and are safe for crops have been developed. Many herbicides developed so far have been registered for specific crops and are used for weed control. Herbicides for use in controlling weeds occurring in the cultivation areas of such specific crops have high herbicidal activity and a broad weeding spectrum, but are preferably safe for the environment and crops. However, not all herbicides fully satisfy these conditions.

As a method for increasing the herbicidal activity of existing herbicides and broadening the herbicidal spectrum, the method most used is a method of mixing two or more herbicidal active substances having different herbicidal activities. In the case of mixing two or more herbicidal active substances as described above, there are cases in which a better herbicidal effect is exhibited than when the herbicides are individually treated (single treatment) to weeds. This case of exhibiting more than the level of potency or activity that would be expected according to the results of the individual potency of the constituents is referred to as "synergy". However, there are some cases where the synergistic action of herbicides appears when two or more herbicidal active substances are mixed, but rather, the herbicidal activity is lower than that of single agent treatment due to differences in different herbicidal properties, absorption, migration, or metabolism of the two herbicides. there are many In this way, a case in which the herbicidal effect is lower when the two herbicidal active substances are mixed than when the single agent is treated is referred to as "antagonism". In addition, the case where the herbicidal effect does not change when the herbicidal active substances are mixed with the single agent treatment is called "additive action".

Pyribenzoxim (PBX) is a herbicide from germination to postemergence and has the action of inhibiting Acetolactate synthase (ALS) activity. Due to its strong soil adsorption properties, it is mainly used for foliage treatment. Conventionally, Pyribenzoxim (PBX) was mainly developed as a single agent, but recently, research on the development of a combination with other herbicidal active substances is being conducted for the emergence of resistant weeds and expansion of the weeding spectrum. On the other hand, Pyribenzoxim (PBX) has been studied in various formulations (WP, WG, OD, SC, etc.), but it has the best efficacy in the Emulsifiable Concentrate (EC) formulation containing a large amount of specific emulsifier. seemed However, in the case of PBX, since a large amount of emulsifier is required for sufficient drug efficacy, the amount of solvent used is limited. As a result, it is difficult to secure formulation stability as a solvent naphtha-based organic solvent commonly used in the development of mixtures. There was a difficult problem.

Therefore, as a pyribenzoxim (Pyribenzoxim, PBX) mixture, it shows excellent herbicidal activity in synergy with pyribenzoxim (PBX), and it is required to develop a herbicide composition having excellent formulation stability of the emulsion (EC) formulation.

[Prior art literature]

[Patent Literature]

Chinese Laid-Open Patent No. 104186503

The present invention is a pyribenzoxim (Pyribenzoxim, PBX) mixture, using a specific herbicidal active substance synergistic with pyribenzoxim (PBX), as well as showing excellent herbicidal activity, and excellent formulation stability (EC) An object of the present invention is to provide a formulation of a herbicide composition.

The present invention includes pyribenzoxim (Pyribenzoxim, PBX), fenoxsulam (Penoxsulam, PNS), an organic solvent and an emulsifier, wherein the organic solvent is gamma-Butyrolactone (GBL) It provides a herbicide composition .

According to the present invention, as a mixture comprising pyribenzoxim (PBX) and phenoxsulam (PNS), an emulsion ( EC) formulations of herbicide compositions.

Hereinafter, the present invention will be described in more detail to help the understanding of the present invention. At this time, the terms or words used in the present specification and claims should not be construed as being limited to conventional or dictionary meanings, and the inventor appropriately defines the concept of the term in order to best describe his invention. Based on the principle that it can be done, it should be interpreted as meaning and concept consistent with the technical idea of the present invention.

The present invention includes pyribenzoxim (Pyribenzoxim, PBX), fenoxsulam (Penoxsulam, PNS), an organic solvent and an emulsifier, wherein the organic solvent is gamma-Butyrolactone (GBL) It provides a herbicide composition .

The pyribenzoxim (Pyribenzoxim, PBX) has the action of inhibiting Acetolactate synthase (ALS) activity as a herbicide from germination to maturity (postemergence). The pyribenzoxim (Pyribenzoxim, PBX) is mainly used for foliage treatment because of its strong soil adsorption properties. Conventionally, Pyribenzoxim (PBX) was mainly developed as a single agent, but recently it was necessary to develop a combination with other herbicidal active substances due to the emergence of resistant weeds and limitations in weeding spectrum. Accordingly, in the present invention, a mixture of the pyribenzoxim (Pyribenzoxim, PBX) and phenoxsulam (Penoxsulam, PNS) was developed. The phenoxulam (Penoxsulam, PNS) can be absorbed through the leaves and roots, and can be used both before the germination of weeds and before the germination of weeds (postemergence). In addition, the phenoxsulam (Penoxsulam, PNS) has a wide control spectrum, such as hyacinth plants, broadleaf weeds, sedge plants. The mixture of the pyribenzoxim (Pyribenzoxim, PBX) and phenoxulam (Penoxsulam, PNS) has excellent fast-acting and drug lasting properties, a broad control spectrum, and excellent herbicidal activity.

On the other hand, although studies on various formulations (WP, WG, OD, SC, etc.) of the pyribenzoxim (PBX) and phenoxsulam (PNS) mixture have been conducted, an emulsifiable agent containing a large amount of a specific emulsifier (Emulsifiable) Concentrate, EC) showed the best efficacy. However, in the case of the emulsion (EC), the amount of the emulsifier is required, so the amount of the solvent is limited, and in the case of the naphtha series or aromatic series organic solvents generally used in the emulsion (EC) formulation. There was a problem in that it was difficult to secure formulation stability. In addition, the pyribenzoxim (Pyribenzoxim, PBX) and phenoxsulam (Penoxsulam, PNS) both had difficulty in developing an emulsion (EC) formulation because their solubility in conventional organic solvents was not high. Therefore, in the present invention, by using gamma-butyrolactone (GBL) as an organic solvent, solubility is increased and pyribenzoxim (PBX) and phenoxylam (PBX) of an emulsion (EC) formulation with excellent formulation stability ( Penoxsulam, PNS) developed a combined herbicide composition.

According to an embodiment of the present invention, 0.1 to 10.0 parts by weight of pyribenzoxim (PBX) may be included with respect to 100 parts by weight of the herbicide composition, more preferably 1.0 to 5.0 parts by weight, more preferably It may contain 2.5 to 3.0 parts by weight. In addition, according to an embodiment of the present invention, 0.1 to 10.0 parts by weight of phenoxsulam (PNS) may be included with respect to 100 parts by weight of the herbicide composition, more preferably 1.0 to 5.0 parts by weight, more preferably may include 1.5 to 2.0 parts by weight. Most preferably, it may include 2.5 to 3.0 parts by weight of pyribenzoxim (PBX) and 1.5 to 2.0 parts by weight of phenoxsulam (PNS) based on 100 parts by weight of the herbicide composition. In addition, the pyribenzoxim (Pyribenzoxim, PBX) and phenoxsulam (Penoxsulam, PNS) may be included in a weight ratio of 1:0.1 to 1:3.0, more preferably from 1:0.2 to 1:1.0 by weight. and more preferably 1:0.5 to 1:0.8 by weight. By including the pyribenzoxim (Pyribenzoxim, PBX) and phenoxulam (Penoxsulam, PNS) within the weight range, the pyribenzoxim (Pyribenzoxim, PBX) and the phenoxulam (Penoxsulam, PNS) show excellent herbicidal activity due to synergy and may have excellent fast-acting and long-acting drug effects.

On the other hand, the herbicide composition of the present invention may be an emulsion (EC) formulation including an organic solvent and an emulsifier, and excellent medicinal efficacy can be secured by forming the herbicide composition into an emulsion (EC) formulation. However, in the case of the emulsion (EC) formulation, the solubility of pyribenzoxim (PBX) and phenoxsulam (PNS) is not high, and there was a problem in that it was difficult to secure formulation stability, but the present invention is gamma-butyric as an organic solvent By including Rolactone (gamma-Butyrolactone, GBL), it is possible to dissolve well and secure excellent formulation stability. 50 to 70 parts by weight of the gamma-butyrolactone (GBL) with respect to 100 parts by weight of the herbicide composition, more preferably 60 to 68 parts by weight, more preferably 64 to 66 parts by weight may include wealth. By including the gamma-butyrolactone (gamma-Butyrolactone, GBL) within the above weight range, there is an effect of preventing low-temperature precipitation of the original agent.

The emulsifier included in the herbicide composition of the present invention may be at least one selected from the group consisting of anionic, non-ionic and cationic, and specifically, an alkylaryl ether sulfate salt ( alkylaryl ether sulfate salt, phosphate ester salt, sulfosuccinate salt, alcohol ether ethoxylate, alcohol ether alkoxylate, alkylphenol ether Ethoxylate (alkylphenol ether ethoxylate), alkylphenol ether alkoxylate (alcoholphenol ether alkoxylate), block copolymer (block co-polymer), fatty acid alkoxylate (fatty acid alkoxylate), fatty amine alkoxylate (fatty amine alkoxylate), Alkyl polyglucoside, alkoxylated vegetable oil, sorbitol ester alkoxylate, amine oxide, fatty amine alkoxylate, and quaternary It may be at least one selected from the group consisting of an ammonium salt (Quaternary ammonium salt), and more preferably, as the emulsifier, polyoxyethylene lauryl ether (polyoxyethylene lauryl ether) and polyethylene-polypropylene copolymer (polyethylene-polypropylene copolymer) may include The emulsifier makes the droplet size of the emulsion to a nanometer level, thereby maximizing the foliar penetration of pyribenzoxim (PBX). The emulsifier may be included in an amount of 15 to 45 parts by weight based on 100 parts by weight of the herbicide composition, and more preferably 25 to 35 parts by weight. By including the emulsifier in the above weight range, the droplet size of the emulsion is made at the nanometer level, thereby maximizing the foliar penetration of Pyribenzoxim (PBX) and Penoxsulam (PNS).

The following examples are presented to provide those skilled in the art with a complete disclosure and description of how the compounds, compositions, and methods provided herein are made and evaluated, and are intended to be purely illustrative. Accordingly, the examples are in no way intended to limit the scope of what the inventors regard as their invention. There are many variations and combinations of reaction conditions, eg, component concentrations, desired solvents, solvent mixtures, temperature, pressure, and other reaction parameters and conditions that may be used to optimize product properties such as purity, yield, and the like. These are also considered to be within the scope of this application. Any combination of the elements described above in all possible variations is encompassed by the invention unless otherwise indicated herein or otherwise clearly contradicted by context.

[Experimental Example 1: Formulation stability evaluation]

3 g of pyribenzoxim (PBX) and 2 g of phenoxsulam (PNS) were mixed in 65 g of each solvent according to Table 1, and dissolved by stirring at 50 ° C. with a stirrer at 400 rpm. Then, it was stored at a low temperature (0°C) for 2 weeks to check whether the original agent was precipitated, and dissolution stability was evaluated.

menstruum	Whether the original agent is dissolved	Whether the original agent is precipitated (2 weeks storage)
K-200S (solvent naphtha, heavy aromatic compound)	X	O
K-150 (solvent naphtha, heavy aromatic compound)	X	O
K-100 (solvent naphtha, light aromatic compound)	X	O
CR-MO (methyl oleate)	X	O
AG-1555 (propylene carbonate)	X	O
AG-1730 (morphine amide, C8-C10 fatty acid)	X	O
cotton seed oil	X	O
castor oil	X	O
NMP (N-methylpyrrolidone)	O	O
NOP (N-octylpyrollidone)	X	O
exxsol D-100 (Hydrocarbons, C12-C15, n-alkanes)	X	O
exxsol D-130 (Distillates (petroleum), hydrotreated middle)	X	O
AMD810 (C8-C10 fatty acid dimethylamide)	X	O
Xylene	X	O
GBL (gamma-Butyrolactone)	O	X

Referring to Table 1, NMP and gamma-butyrolactone (GBL) in various solvents dissolved the original agent, but precipitation of NMP occurred when stored at a low temperature. Gamma-butyrolactone (GBL) was not only well-dissolved, but also had excellent dissolution stability because precipitation did not occur when stored at a low temperature.

Example 1

Pyribenzoxim (PBX) 3g, phenoxsulam (Penoxsulam, PNS) 2g was mixed with gamma-butyrolactone (gamma-Butyrolactone, GBL) 65g, and dissolved by stirring at 50 ℃ with a stirrer 400rpm. After confirming that it was dissolved visually, and after stopping heating, add a total of 30 g of emulsifier polyoxyethylene lauryl ether and polyethylene-polypropylene copolymer, and stir sufficiently with a stirrer 400rpm to prepare a herbicide composition of an emulsion (EC) formulation.

Comparative Example 1

Pyribenzoxim (Pyribenzoxim, PBX) single agent (trade name: pyanchor) of an emulsion (EC) formulation containing 5 g of pyribenzoxim (PBX) was prepared. In addition, a single drug (Penoxsulam, PNS) (trade name: Salchodaecheop) in the form of a suspension concentrate (SC) containing 3 g of phenoxsulam (PNS) was prepared. The pyribenzoxim (Pyribenzoxim, PBX) single agent and the phenoxsulam (Penoxsulam, PNS) single agent were mixed and used immediately before drug treatment.

Comparative Example 2

An emulsion (EC) herbicide composition (trade name: Pyanchor gold) containing 6 g of cyhalofop butyl (CHF) and 2.5 g of pyribenzoxim (PBX) was used.

Comparative Example 3

A herbicide composition (trade name: Topshot) of an oily wetting agent (OD) formulation containing 5 g of cyhalofop butyl (CHF) and 1 g of phenoxsulam (PNS) was used.

[Experimental Example 2: Efficacy evaluation]

The herbicidal efficacy was evaluated using the herbicide compositions of Example 1 and Comparative Examples 1 to 3. Specifically, for the target weeds, 3-4 leaf stages (resistance, susceptibility), dung beetle, algae, and honeysuckle were used. During treatment, weed growth period was around 4 leaf stage, and pre-emergence was 2 days after weed sowing. It was. The amount of water used when diluting the product was based on 300L/ha, and the herbicidal activity was observed with the naked eye on the 8th, 14th, and 26th days after the drug treatment. Before and after treatment, pot management was performed with foliage treatment after complete drainage, and freshwater depth of 1 cm was maintained 24 hours after treatment.

The results are shown in Table 2 below.

	Example 1	Comparative Example 1	Comparative Example 2	Comparative Example 3
	Day 8
Hard skin (resistance) 3-4 LS (leaf stage)	93	88	82	50
Hard skin (susceptibility) 3-4LS	93	88	80	85
Dungeon 4~6LS	70	40	95	90
Albang Dongsani 4~5LS	97	85	30	40
Switch needle 3~3.5LS	99	80	100	30
	Example 1	Comparative Example 1	Comparative Example 2	Comparative Example 3
	Day 8
Hard skin (resistance) pre-E	99	99	98	85
Hard skin (susceptibility) pre-E	99	97	98	30
dung beetle pre-E	99	100	99	17
	Example 1	Comparative Example 1	Comparative Example 2	Comparative Example 3
	Day 14
Hard skin (resistance) 3-4LS	100	100	94	70
Hard skin (susceptibility) 3-4LS	100	100	100	85
Dungeon 4~6LS	70	35	97	100
Albang Dongsani 4~5LS	100	99	50	30
Switch needle 3~3.5LS	100	100	100	30
	Example 1	Comparative Example 1	Comparative Example 2	Comparative Example 3
	Day 14
Hard skin (resistance) pre-E	100	100	100	33
Hard skin (susceptibility) pre-E	100	100	100	7
dung beetle pre-E	100	100	100	13
Albangdongsanni pre-E	100	100	93	80
	Example 1	Comparative Example 1	Comparative Example 2	Comparative Example 3
	Day 26
Hard skin (resistance) 3-4LS	100	100	93	40
Hard skin (susceptibility) 3-4LS	100	100	100	69
Dungeon 4~6LS	60	40	83	100
Albang Dongsani 4~5LS	100	100	55	20
Switch needle 3~3.5LS	100	100	100	20
	Example 1	Comparative Example 1	Comparative Example 2	Comparative Example 3
	Day 26
Hard skin (resistance) pre-E	100	100	100	27
Hard skin (susceptibility) pre-E	100	100	100	3
dung beetle pre-E	100	100	100	13
Albangdongsanni pre-E	100	100	100	92

Referring to Table 2, compared to Comparative Example 1, the herbicidal composition according to Example 1 was excellent in herbicidal activity. In addition, compared to Comparative Examples 2 to 3, the herbicidal composition according to Example 1 showed fast and excellent herbicidal activity against lice (resistance), lichen (susceptibility), algae, and chrysanthemum. was low.

Claims (10)

1. Pyribenzoxim (PBX), Penoxsulam (PNS), organic solvents and emulsifiers,

   The organic solvent is gamma-butyrolactone (gamma-Butyrolactone, GBL) herbicide composition.
2. According to claim 1,

   The herbicide composition is a herbicide composition, characterized in that the emulsion (Emulsifiable Concentrate, EC) formulation.
3. According to claim 1,

   A herbicide composition comprising 0.1 to 10 parts by weight of pyribenzoxim (PBX) with respect to 100 parts by weight of the herbicide composition.
4. According to claim 1,

   A herbicide composition comprising 0.1 to 10 parts by weight of phenoxsulam (PNS) with respect to 100 parts by weight of the herbicide composition.
5. According to claim 1,

   The pyribenzoxim (Pyribenzoxim, PBX) and phenoxsulam (Penoxsulam, PNS) are 1:0.1 to 1:3.0 herbicide composition included in a weight ratio.
6. According to claim 1,

   A herbicide composition comprising 2.5 to 3.0 parts by weight of pyribenzoxim (PBX) and 1.5 to 2.0 parts by weight of phenoxsulam (PNS) based on 100 parts by weight of the herbicide composition.
7. According to claim 1,

   A herbicide composition comprising 50 to 70 parts by weight of gamma-butyrolactone (GBL) with respect to 100 parts by weight of the herbicide composition.
8. According to claim 1,

   The emulsifier is an alkylaryl ether sulfate salt, a phosphate ester salt, a sulfosuccinate salt, an alcohol ether ethoxylate, an alcohol ether alkoxylate. (alcohol ether alkoxylate), alkylphenol ether ethoxylate, alkylphenol ether alkoxylate, block co-polymer, fatty acid alkoxylate, fat Fatty amine alkoxylate, alkyl polyglucoside, alkoxylated vegetable oil, sorbitol ester alkoxylate, amine oxide, aliphatic amine alkoxylate (fatty amine alkoxylate), and at least one herbicide composition selected from the group consisting of quaternary ammonium salts.
9. According to claim 1,

   The emulsifier is polyoxyethylene lauryl ether (polyoxyethylene lauryl ether) and polyethylene- a herbicide composition comprising a polypropylene copolymer (polyethylene-polypropylene copolymer).
10. According to claim 1,

    A herbicide composition comprising 15 to 45 parts by weight of an emulsifier based on 100 parts by weight of the herbicide composition.