KR102059980B1 - Liquid herbicidal composition - Google Patents

Abstract

The present invention relates to a liquid herbicide composition, and more particularly, to provide a liquid herbicide composition comprising an active ingredient comprising a pyridinesulfonylurea compound represented by Formula 1 and a buffer having a pH of 5.80 to 6.25, excellent herbicidal activity Of course, liquid formulations, particularly liquid hydration formulations are improved stability to provide a liquid herbicide composition that is easy to store organs.

Description

Liquid herbicide composition {LIQUID HERBICIDAL COMPOSITION}

The present invention relates to a liquid herbicide composition, and more particularly to a liquid herbicide composition containing a herbicidal active ingredient exhibiting excellent herbicidal activity.

In crop cultivation technology, it is important to protect crops by controlling weeds that inhibit crop growth. In order to reduce damages such as poor growth or yield reduction of crops caused by weeds in crop plantations, safe herbicides have been developed that can effectively control them and to crops. Many herbicides developed to date have been registered for specific crops and used for weed control. The herbicidal active substance for use in the control of weeds occurring in the cultivation of such specific crops has high herbicidal activity and has a broad herbicidal spectrum, but is safe for the environment and crops.

On the other hand, the herbicide composition comprising the herbicidal active material as described above is a formulation such as wettable powder, emulsion (emulsifiable concentrate), water-dispersible granule, granules, liquid concentrate (Suspension concentrate) Developed and used as herbicide. However, in the case of a hydrating agent, an emulsion, and a granulating agent, it is generally diluted to a predetermined concentration with water and manufactured as a spraying solution. However, a large amount of spraying liquid requires excessive cost and time to uniformly spray the entire surface of the paddy field or field. have. In the case of granules, it can be used directly as it is, the problem of the hydrating agent, emulsion and granulating agent could be solved, but the herbicidal active substance content is relatively small on the basis of the total herbicide, and supplementary agents for forming herbicides must be included. There is a problem that the manufacturing process such as crushing, mixing, drawing, granulation, drying, classification, etc. is complicated, and spray stains occur. In order to overcome the problems of the formulations, a liquid concentrate formulation has been developed that is relatively simple, environmentally friendly, and can be simplified and efficient at the time of application. On the other hand, when used as a herbicide of various formulations, it is an important task to ensure the stability of the herbicide composition even during long-term storage.

The compound of formula a [ISO Proposal Name: flucetosulfuron] is a herbicidal active substance belonging to sulfonylurea system and is herbicidally active in Korean Patent No. 10-0399366 (Application No. 10-2000-0059990). It has already been described as a substance.

[Formula a]

The flucetosulfuron is safe for these crops when treated with soil or foliage against rice, wheat, barley (appropriate dosage: 10-40 g ai / ha) and grass (appropriate dosage: 50-200 g ai / ha), It is known to have excellent herbicidal effect on a wide range of herb species, including broadleaf weeds, flowering and weeds, forage weeds, annual and perennial weeds.

However, it is still a problem to ensure the stability of the herbicide composition comprising the herbicidal active substance belonging to the sulfonylurea system as described above. In particular, in the case of liquid concentrate (Suspension concentrate, SC) formulation there is a problem that is difficult to be stored for a long time because the stability is further reduced by hydrolysis at high temperature storage conditions.

Republic of Korea Patent Publication No. 10-0399366

An object of the present invention is to solve the problems of the prior art, and to provide a liquid herbicide composition having excellent herbicidal activity, excellent stability even in liquid formulations and easy storage at high temperatures for a long time.

The present invention comprises an active ingredient comprising a pyridinesulfonyl urea compound represented by the formula (1); And it provides a liquid herbicide composition comprising a buffer having a pH of 5.80 to 6.25.

[Formula 1]

In Chemical Formula 1,

n represents an integer of 1 to 3,

R is hydrogen or an alkyl group having 1 to 4 carbon atoms,

R 'is hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, a halogen group or an alkoxy group having 1 to 2 carbon atoms,

X and Y are each independently an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, a haloalkoxy group having 1 to 2 carbon atoms or a halogen group.

According to the present invention, in the herbicide composition, excellent herbicidal activity, liquid herbicide composition of low disintegration rate and excellent stability even in the form of liquid concentrate (Suspension concentrate, SC), easy to be stored for a long time at high temperature as a herbicide Can be provided.

Hereinafter, the present invention will be described in detail.

The terms or words used in this specification and claims are not to be construed as being limited to their ordinary or dictionary meanings, and the inventors may appropriately define the concept of terms in order to best describe their invention. It should be interpreted as meaning and concept corresponding to the technical idea of the present invention based on the principle that the present invention.

Liquid herbicide composition according to an embodiment of the present invention is an active ingredient comprising a pyridinesulfonyl urea compound represented by the formula (1); And a buffer having a pH of 5.80 to 6.25.

[Formula 1]

In Formula 1, n represents an integer of 1 to 3, R is hydrogen or an alkyl group having 1 to 4 carbon atoms, R 'is hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, a halogen group or An alkoxy group having 1 to 2 carbon atoms, X and Y are each independently an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, a haloalkoxy group having 1 to 2 carbon atoms, or a halogen group.

More preferably, the pyridinesulfonylurea compound represented by Formula 1 is represented by Formula 1, wherein n is an integer of 1 or 2, R is hydrogen or methyl, R 'is hydrogen, halogen or methyl, and X is And Y may each independently be a compound that is a methoxy group, more preferably n is an integer of 1 or 2, R is a methyl group, R 'is hydrogen, chlorine (Cl), bromine (Br) or a methyl group, X and Y may each independently be a methoxy group.

The pyridinesulfonylurea compound of Formula 1 according to an embodiment of the present invention may be, for example, N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (2- Fluoro-1-methoxyacetoxy-n-propyl) pyridine-3-sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (2-fluoro Rho-1-hydroxyacetoxy-n-propyl) pyridine-3-sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (2-fluoro -1- (3-hydroxypropion) oxy-n-propyl) pyridine-3-sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (2 -Fluoro-1- (3-methoxypropion) oxy-n-propyl) pyridine-3-sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -4 -Methyl-2- (2-fluoro-1-methoxyacetoxy-n-propyl) pyridine-3-sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl ] -4-chloro-2- (2-fluoro-1-methoxy Acetoxy-n-propyl) pyridine-3-sulfonamide and N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -4-bromo-2- (2-fluoro- At least one compound selected from 1-methoxyacetoxy-n-propyl) pyridine-3-sulfonamide.

More preferably, the pyridinesulfonyl urea compound represented by Chemical Formula 1 may be a compound of Chemical Formula 2 (ISO proposal name: flucetosulfuron).

[Formula 2]

In the liquid herbicide composition according to an embodiment of the present invention, the active ingredient is 1 part by weight to 50 parts by weight, preferably 1 part by weight to 25 parts by weight, and even more preferably 3 based on 100 parts by weight of the liquid herbicide composition. It may include 15 parts by weight to parts. When the active ingredient of the liquid herbicide composition is included in less than 1 part by weight, even if only a small amount of the active ingredient is decomposed due to the amount of the active ingredient present in the herbicide composition, the decomposition rate (%) is relatively increased, so the herbicidal effect is lowered. May occur, and when the active ingredient is included in an amount exceeding 50 parts by weight, a problem may occur such that the physical properties of the product, such as increasing the viscosity.

On the other hand, in the case of liquid formulations, there was a problem that the stability is poor due to hydrolysis of the active ingredient comprising a pyridinesulfonyl urea compound represented by the formula (1). However, the liquid herbicide composition according to one embodiment of the present invention by appropriately adjusting the pH of the buffer to ensure a stable degradation rate in the liquid formulation significantly lowered.

Liquid herbicide composition according to an embodiment of the present invention may have a pH of 5.80 to 6.25, preferably pH 6.00 to pH 6.20, even more preferably pH 6.10 to pH 6.20, the pH is a buffer (buffer) Can be adjusted. That is, the liquid herbicide composition of the present invention may comprise a buffer having a pH of 5.80 to 6.25, preferably 6.00 to 6.20, even more preferably 6.10 to 6.20. In the present invention, the pH of the liquid herbicide composition is one of the factors affecting the decomposition rate by hydrolysis of the liquid herbicide composition, and when the pH range of 5.80 to 6.25 is satisfied, the decomposition rate is low even during long-term high temperature storage of the liquid herbicide composition. Stability is greatly improved.

The buffer may preferably be a phosphate-based buffer, a mixture of carbonic acid and sodium bicarbonate (H ₂ CO ₃ / NaHCO ₃ mixture) or a bis-tris solution, specifically dipotassium hydrogen phosphate (K ₂ HPO ₄ ), potassium dihydrogen phosphate (KH ₂ PO ₄ ), disodium hydrogen phosphate (Na ₂ HPO ₄ ), sodium dihydrogen phosphate (NaH ₂ PO ₄ ), a mixture of carbonic acid and sodium bicarbonate (H ₂ CO ₃ / NaHCO ₃ mixture) and Bis-Tris solution may be selected from one or more, and more specifically, dipotassium hydrogen phosphate, potassium dihydrogen phosphate, disodium hydrogen phosphate, sodium dihydrogen phosphate or Mixtures thereof.

In addition, when the buffer is mixed, the mixing ratio of each buffer may be adjusted at a rate such that the pH of the entire buffer is 5.80 to 6.25.

In the present specification, "Bis-Tris solution" is a solution including Bis-Tris, and Bis-Tris is a compound well known to those skilled in the art, and the IUPAC name is 2- [Bis (2-hydroxyethyl) amino] -2- (hydroxymethyl) propane-1,3-diol, CAS number is 6976-37-0.

Further, the buffer may be a solution of 0.03 M to 0.2 M, preferably 0.05 M to 0.1 M concentration. When the buffer satisfies the above numerical range, the decomposition rate of the liquid herbicide composition is further lowered, and stability is improved. In addition, when the concentration is less than 0.2M as in the present invention has excellent viscosity physical properties there is an advantage that the production of herbicide composition is easy.

Liquid herbicide composition according to an embodiment of the present invention may further include a surfactant, the surfactant may facilitate the wettability, dispersibility of the active ingredient and also help to maintain the suspension stability of the composition for a long time .

In addition, the surfactant may include 1 part by weight to 20 parts by weight, specifically 1 part by weight to 10 parts by weight, based on 100 parts by weight of the total liquid herbicide composition.

As the type of the surfactant, anionic surfactants, nonionic surfactants, in particular nonionic surfactants may be used a polymeric surfactant, specifically, sodium salt dioctyl sulfosuccinic acid as anionic surfactant Oxirane graft aerials containing dioctyl sulfosuccinate Sodium salt, dioctyl sulfosuccinate Calcuim salt or alpha olefin sulfonate surfactants and comprising ethylene oxide units as nonionic surfactants Copolymers, copolymers of oxyethylene and oxypropylene, polyoxyethylene tristyryl phenyl ether or carboxylate based polymers, sucrose laurate surfactants can be used.

Liquid herbicide composition according to an embodiment of the present invention may further comprise a cryoprotectant, wherein the cryoprotectant is 0.01 parts by weight to 10 parts by weight, specifically 1.0 parts by weight to 6.0 based on 100 parts by weight of the total liquid herbicide composition Part by weight, more specifically, it may include 2.0 parts by weight to 4.0 parts by weight, and more specifically in terms of significantly improving the decomposition rate at the same time having an anti-freezing effect may more specifically include 2.0 parts by weight to 3.0 parts by weight.

In addition, the cryoprotectant may include an alcohol-based compound, and may specifically include a glycol-based compound such as propylene glycol (PG), ethylene glycol, diethylene glycol, dipropylene glycol, tripropylene glycol, and the like. Alcohol compounds other than glycol compounds may include glycerin, isopropanol, or mixtures thereof, and may more preferably include propylene glycol in terms of improving stability while securing an excellent freeze protection effect.

When the type of cryoprotectant of the present invention is included in the above numerical range, the anti-freezing effect is excellent, as well as the effect of lowering the decomposition rate of the liquid herbicide composition. In other words, when the content ratio of the cryoprotectant exceeds the numerical range, the decomposition rate of the liquid herbicide composition is high, which may cause a problem of poor stability. When included in less than the above numerical range, the content is insignificant, a problem may not occur to implement a sufficient freeze protection effect.

The liquid herbicide composition according to one embodiment of the present invention may include a thickener, and the thickener is 0.001 parts by weight to 1.2 parts by weight or less based on 100 parts by weight of the total liquid herbicide composition. Parts, even more specifically 0.05 parts to 0.15 parts by weight.

In addition, the thickener may be used without limitation, thickeners that can be generally used in the art, specifically, xanthan gum, bentonite, smectite clay, montmorillonite, gum arabic, guar gum, cellulose-based compounds, Sodium alginate, starch or mixtures thereof, preferably xanthan gum, montmorillonite or mixtures thereof.

According to one embodiment of the present invention, when the thickener is included in the numerical range, the thickening effect is improved and at the same time, the decomposition rate of the liquid herbicide composition is lowered.

According to one embodiment of the present invention, in addition to the above components, the liquid herbicide composition may further include an antifoaming agent, a preservative, a stabilizer, a pigment, and the like as needed.

In addition, according to an embodiment of the present invention, the liquid herbicide composition is left without the content of the compound represented by the formula (1) as the active ingredient, surfactant, cryoprotectant, thickener, and additives such as antifoam, preservative, stabilizer The contents can all consist of buffers. In other words, the content of the buffer may be the remainder other than the content of the other components in 100% by weight of the liquid herbicide composition.

In addition, according to an embodiment of the present invention, the formulation of the liquid herbicide composition is not limited to any formulation as long as it is a liquid formulation, specifically, may be a solution formulation or a liquid concentrate (SC) formulation that is present in the liquid phase And even more specifically, a liquid hydration formulation. Here, the liquid hydration formulation may mean a water-dispersed suspension form.

When the herbicide composition containing the above-mentioned active ingredient is prepared as a liquid hydrating agent formulation, there is a problem in that long-term storage is not easy even when the herbicide composition is prepared due to high decomposition rate due to hydrolysis. In the present invention, the pH of the liquid herbicide composition is adjusted. As a result, it is possible to produce a liquid herbicide composition having improved stability and easy storage for a long time.

The liquid herbicide composition according to one embodiment of the present invention protects the sulfonylurea group of the pyridinesulfonylurea compound from hydrolysis even though the liquid formulation is controlled by adjusting the pH range of the liquid herbicide composition including a pH controlled buffer solution. Thus, the decomposition rate due to hydrolysis is significantly lowered to ensure the stability of the liquid formulation, and can be easily stored for a long time. As described above, the present invention can solve the problem that it is difficult to secure stability because most of the active ingredients are hydrolyzed because the decomposition rate by the hydrolysis of the liquid formulation herbicide composition containing a small amount of the active ingredient is very large.

Example

Hereinafter, preferred examples are provided to aid in understanding the present invention, but the following examples are merely for exemplifying the present invention, and various changes and modifications within the scope and spirit of the present invention are apparent to those skilled in the art. It is natural that such variations and modifications fall within the scope of the appended claims.

Example 1

The manufacturing process is divided into two parts, the wet part and the thickening part, and is performed at room temperature.

Potassium hydrogen phosphate (K ₂ HPO ₄ ) and potassium dihydrogen phosphate (KH ₂ PO ₄ ) were supplemented with water to make a 1 L solution to prepare a phosphate buffer of 0.1 M, pH 6.15. Then 65.8 parts by weight of the buffer CR-DOS70P (di (2-ethylhexyl) sulfosuccinate; Di (2-ethylhexyl) sulfosuccinate, sodium salt, Cas no. 577-11-7) 3.0 parts by weight, NK-SU500 (Sucrose laurate; sucrose laurate, cas no.25339-99-5) Add 1.0 parts by weight and 0.2 parts by weight of antifoaming agent SAG-622 (momentive) and mix thoroughly to make 1- (3-{[( 4,6-dimethoxy-pyrimidin-2-yl) carbamoyl] sulfamoyl} -2-pyridinyl) -2-fluoropropyl methoxyacetate (Flucetosulfuron, FTS) 10.0 parts by weight, using a stirrer Mixed. A glass bead was added thereto, followed by pulverization, until the particle size average value was 1 to 2 μm, thereby preparing a wet part.

Next, 3.0 parts by weight of propylene glycol (PG; propylene glycol, cas no. 57-55-6) and 0.1 part by weight of xanthan gum (XG; Xanthan Gum, cas no. 11138-66-2), MV [5-chloro 2-methyl-4-isothiazolin-3-one (cas no.26172-55-4) and 2-methyl-4-isothiazolin-3-one (cas no.2682-20-4)] 0.2 Part by weight was added and stirred well. Then add 16.7 parts by weight of 0.1 M, pH 6.15 phosphate buffer mixed with dipotassium hydrogen phosphate (K ₂ HPO ₄ ) and potassium dihydrogen phosphate (KH ₂ PO ₄ ) in water, and stir sufficiently.

After adding 20 parts by weight of the thickening part to 80 parts by weight of the wet part and sufficiently stirring, the herbicide composition of the liquid hydration formulation was prepared.

Example 2

The herbicide composition of the liquid hydration formulation was prepared in the same manner as in Example 1 except that the pHs of the wet and thickener buffers were changed to 5.8.

Example 3

A herbicide composition was prepared in the same manner as in Example 1, except that 2 parts by weight of propylene glycol was added and 17.7 parts by weight of phosphate buffer.

Example 4

A herbicide composition was prepared in the same manner as in Example 1 except that 4 parts by weight of propylene glycol was added and 15.7 parts by weight of phosphate buffer.

Comparative Example 1

The herbicide composition of the liquid hydration formulation was prepared in the same manner as in Example 1 except that the pH of the wet and thickener buffers was changed to 5.5.

Comparative Example 2

The herbicide composition of the liquid hydration formulation was prepared in the same manner as in Example 1 except that the pH of the wet and thickener buffers was changed to 6.3.

Comparative Example 3

The herbicide composition of the liquid hydration formulation was prepared in the same manner as in Example 1 except that the pHs of the wet and thickener buffers were changed to 6.8.

Comparative Example 4

The herbicide composition of the liquid wetting agent formulation was prepared in the same manner as in Example 1 except that the pH of the wet and thickening buffers was changed to 7.4.

Experimental Example: Evaluation of Storage Stability of Liquid Herbicide Composition

To evaluate the storage stability of the liquid herbicide compositions of the Examples and Comparative Examples of the present invention, about 100 ml of the sample was filled into a polyethylene bottle, the lid was closed, and then stored in an oven maintained at 54 (± 2) ° C. for 4 weeks. HPLC (manufacturer: waters) to evaluate the decomposition rate by measuring the area value of the active ingredient and are shown in Table 1 below.

HPLC analysis conditions are as follows.

Column: 100mm X 4.6mm id "Capcell Pak" C ₁₈ column, 3㎛ particles

Mobile Phase: acetonitrile / water (0.02M ammonium acetate + 0.1M acetic acid) = 32/68

Flow: 1.0 mL / min.

Column Temperature: 30 ℃

Injection Volume: 10µl

Detector Wavelength: 254nm

Run time: 20 min.

Degradation rate after 4 weeks at 54 ℃ (%) Example 1 9.94 Example 2 11.42 Example 3 10.72 Example 4 11.59 Comparative Example 1 11.66 Comparative Example 2 12.14 Comparative Example 3 14.49 Comparative Example 4 19.35

As shown in Table 1, Examples 1 to 4 is a liquid herbicide composition comprising a pyridinesulfonyl urea compound as an active ingredient and a buffer having a pH of 5.80 to 6.25 according to an embodiment of the present invention is the pH of the buffer Compared with Comparative Examples 1 to 4 outside the scope of the present invention, the decomposition rate is low, and it can be confirmed that stability is excellent even at high temperature storage for a long time.

In addition, among the examples, when the pH of the buffer is the same, it can be seen that the decomposition rate of Examples 1 and 3 including 2.0 to 3.0 parts by weight of a cryoprotectant is lower.

Although the present invention has been described by specific embodiments such as specific components and the like, but the embodiments and the drawings are provided to assist in a more general understanding of the present invention, the present invention is not limited to the above embodiments. For those skilled in the art, various modifications and variations can be made from these descriptions.

Accordingly, the spirit of the present invention should not be limited to the above-described embodiments, and all of the equivalents or equivalents of the claims, as well as the appended claims, fall within the scope of the spirit of the present invention. I will say.

Claims (13)

An active ingredient comprising a pyridinesulfonylurea compound represented by Formula 1 below; And
A liquid herbicide composition comprising a buffer having a pH of 6.0 to 6.2.
[Formula 1]

In Chemical Formula 1,
n is an integer of 1 to 3,
R is hydrogen or an alkyl group having 1 to 4 carbon atoms,
R 'is hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, a halogen group or an alkoxy group having 1 to 2 carbon atoms,
X and Y are each independently an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, a haloalkoxy group having 1 to 2 carbon atoms or a halogen group.
delete The method of claim 1,
The buffer solution is a liquid herbicide composition comprising at least one selected from the group consisting of a phosphate-based buffer, a mixture of carbonic acid and sodium bicarbonate (H ₂ CO ₃ / NaHCO ₃ mixture) and bis-Tris (Bis-Tris) solution .
The method of claim 3,
The phosphate buffer is selected from the group consisting of dipotassium hydrogen phosphate (K ₂ HPO ₄ ), potassium dihydrogen phosphate (KH ₂ PO ₄ ), disodium hydrogen phosphate (Na ₂ HPO ₄ ) and sodium dihydrogen phosphate (NaH ₂ PO ₄ ). Liquid herbicide composition comprising at least one selected.
The method of claim 1,
The buffer is a liquid herbicide composition of which the concentration is 0.03 M to 0.2 M.
The method of claim 1,
In Chemical Formula 1,
n is an integer of 1 or 2,
R is hydrogen or a methyl group,
R 'is hydrogen, a halogen group or a methyl group,
X and Y are each independently a liquid herbicide composition methoxy group.
The method of claim 1,
Pyridinesulfonyl urea compound represented by the formula (1),
N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (2-fluoro-1-methoxyacetoxy-n-propyl) pyridine-3-sulfonamide, N -[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (2-fluoro-1-hydroxyacetoxy-n-propyl) pyridine-3-sulfonamide, N- [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (2-fluoro-1- (3-hydroxypropion) oxy-n-propyl) pyridine-3-sulfonamide , N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (2-fluoro-1- (3-methoxypropion) oxy-n-propyl) pyridine-3 Sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -4-methyl-2- (2-fluoro-1-methoxyacetoxy-n-propyl) Pyridine-3-sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -4-chloro-2- (2-fluoro-1-methoxyacetoxy-n -Propyl) pyridine-3-sulfonamide and N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -4-bromo- A liquid herbicide composition comprising one or more selected from the group consisting of 2- (2-fluoro-1-methoxyacetoxy-n-propyl) pyridine-3-sulfonamide.
The method of claim 1,
Pyridinesulfonylurea compound represented by the formula (1) is a liquid herbicide composition is a compound represented by the formula (2).
[Formula 2]

The method of claim 1,
The active ingredient is a liquid herbicide composition comprising 1 to 50 parts by weight based on 100 parts by weight of the liquid herbicide composition.
The method of claim 1,
The liquid herbicide composition further comprises a cryoprotectant,
The cryoprotectant is a liquid herbicide composition comprising an alcohol compound.
The method of claim 10,
The cryoprotectant is a liquid herbicide composition comprising at least one selected from the group consisting of propylene glycol, ethylene glycol, diethylene glycol, dipropylene glycol, tripropylene glycol, glycerin and isopropanol.
The method of claim 10,
The cryoprotectant is a liquid herbicide composition comprising 0.01 to 10.0 parts by weight based on 100 parts by weight of the liquid herbicide composition.
The method of claim 1,
The liquid herbicide composition is a liquid herbicide composition, characterized in that the suspension concentrate (SC) formulation.