TW202301983A - Herbicide composition - Google Patents

Abstract

The present invention provides a herbicide composition comprising penoxsulam, an organic solvent and an emulsifier, wherein the organic solvent comprises gamma-butyrolactone. The herbicide composition has an emulsifiable concentrate (EC) formulation and excellent weeding effects, and at the same time, since the gamma-butyrolactone is included as the organic solvent, the solubility of the penoxsulam may be excellent, formulation stability may be excellent, and suppressing effects of precipitation phenomenon at a low temperature may be achieved.

Description

Herbicide composition

Cross-reference to related applications

This case claims Korean Patent Application No. 10-2021-0032292 (filed on March 11, 2021) and Korean Patent Application No. 10-2022-0029634 (filed on March 8, 2022) of the Korean Intellectual Property Office. application), the disclosure of which is incorporated herein by reference in its entirety. technical field

This invention relates to herbicide compositions.

In crop cultivation techniques, it is important to protect crops by controlling weeds that inhibit their growth. In order to reduce damages such as poor crop growth and yield reduction due to weed growth when crops are planted, herbicidal active substances that are effective in controlling weeds but are safe for crops have been developed. Various herbicides registered for specific crops and for controlling weeds have been developed so far. Herbicides for controlling the growth of weeds in specific crops are preferably herbicides that have high herbicidal activity and a wide range of herbicides but are safe to the environment and crops.

Penoxsulam (PNS) can be absorbed through leaves and roots, and can be used for postemergence and preemergence of weeds. In addition, flat-speed rot has a wide herbicidal spectrum, including Gramineae weeds, broadleaf weeds, Cyperaceae weeds, etc.

In terms of adequate drug performance, emulsion (emulsifiable concentrate) (EC) formulations containing a large amount of specific emulsifiers are the most suitable, but the solubility in conventional organic solvents commonly used in emulsion (EC) formulations is not high, and it is difficult to ensure Stability of emulsion (EC) formulations. Therefore, currently only suspension concentrate (SC) formulations are used as commercialized formulations (single formulations) in China, and we are continuing to expand the availability of flat-speed rotten formulations to expand diversified formulations Research on substances (WP, WG, OD, SC, etc.).

Therefore, there is a need to develop herbicide compositions exhibiting excellent herbicidal activity and having excellent formulation stability, which are herbicide compositions comprising smooth rotten emulsion (EC) formulations.

[Prior Technical Document]

[Patent Document]

(Patent Document 1) Korean Registered Patent Publication No. 10-2015314 (August 22, 2019)

technical problem

The present invention provides a herbicide composition exhibiting excellent herbicidal activity and having excellent formulation stability, which is a herbicide composition comprising a flattened emulsion (EC) formulation. Technical solutions

The present invention provides a herbicide composition, which comprises molasses, an organic solvent and an emulsifier (emulsifier), wherein the organic solvent comprises gamma-butyrolactone (GBL). beneficial effect

The herbicide composition according to the present invention is an emulsion (EC) formulation comprising rotten and an emulsifier, which exhibits an excellent herbicidal effect, and exhibits an excellent rotten effect by including γ-butyrolactone as an organic solvent. Solubility, resulting in excellent formulation stability and the effect of inhibiting precipitation at low temperatures.

In addition, as another embodiment, the herbicide composition according to the present invention contains gamma-butyrolactone and dimethyl oxene together as an organic solvent, and can further improve the solubility of Pingsulan, so that it is easy to express the drug effect, And with further improved formulation stability.

Hereinafter, the present invention is described in more detail to enable a clearer understanding of the present invention. In this case, it will be understood that the words or terms used in the specification and claims should not be interpreted as the meanings defined in commonly used dictionaries. It should be further understood that based on the principle that the inventor can properly define the meaning of words or terms to best interpret the present invention, these words or terms should be interpreted as having meanings consistent with their meanings in the relevant technical content and the technical concept of the present invention .

The present invention provides a herbicide composition exhibiting excellent herbicidal activity and having excellent formulation stability, which is a herbicide composition comprising a smooth rotten emulsion (EC).

Penoxsulam can be absorbed through leaves and roots, and can be used for postemergence and preemergence of weeds. In addition, flat-speed rot has a wide herbicidal spectrum, including Gramineae weeds, broadleaf weeds, Cyperaceae weeds, etc. The herbicide composition of the present invention has an emulsifiable concentrate (EC) formulation (emulsifiable concentrate (EC) formulation) and contains a large amount of emulsifier, and has excellent performance as a drug that is flat and fast, and contains γ-butyrolactone as an organic solvent, and, It can be easily dissolved and ensure the stability of the formulation to inhibit the precipitation at low temperature.

In one embodiment, based on 100 parts by weight of the herbicide composition, it may contain 0.1 to 13.5 parts by weight of smooth rot, more preferably 1.0 to 13.0 parts by weight, more preferably 1.5 to 12.0 parts by weight, Still more preferably, it is 2.0 to 10.0 parts by weight. More preferably, based on 100 parts by weight of the herbicide composition, it may contain 2.0 to 7.0 parts by weight, or 2.0 to 3.0 parts by weight of flat speed rot.

The herbicide composition of the present invention can have an emulsion (EC) formulation comprising an organic solvent and an emulsifier, and, by forming the emulsion (EC), excellent pharmaceutical effects can be secured. However, in the case of emulsion (EC) formulations, there are problems that the solubility of flattened rot is not high and it is difficult to ensure the stability of the formulation. However, in the present invention, γ-butyrolactone is included as an organic solvent, the dissolution is performed well, and excellent formulation stability can be ensured.

Based on 100 parts by weight of the herbicide composition, it may contain 50 to 99 parts by weight of γ-butyrolactone, preferably 50 to 95 parts by weight, or 55 to 90 parts by weight, or 60 to 85 parts by weight, Or 62 to 80 parts by weight, or 63 to 75 parts by weight, or 65 to 72 parts by weight.

According to needs, based on 100 parts by weight of the herbicide composition, it can contain 40 to 85 parts by weight, or 45 to 85 parts by weight, or 50 to 85 parts by weight, or 45 to 80 parts by weight, or 45 to 75 parts by weight parts, or 45 to 70 parts by weight, or 50 to 65 parts by weight, or 50 to 60 parts by weight, or 50 to 55 parts by weight of γ-butyrolactone. By including γ-butyrolactone in the above weight range, the dissolution proceeds well, ensures excellent formulation stability, and prevents precipitation of original materials at low temperatures.

In addition, the herbicide composition of the present invention may further include dimethyl sulfoxide (DMSO) as an organic solvent. In this case, the solubility of the herbicide in the organic solvent can be further improved, and has the advantage of using the present invention. The advantage that the drug effect of the herbicide composition becomes easier.

Based on 100 parts by weight of the herbicide composition, it may contain 4 to 25 parts by weight of dimethyl ethylene oxide, preferably 5 to 25 parts by weight, or 7 to 22 parts by weight, or 10 to 20 parts by weight, and more Preferably it is 12 to 17 parts by weight, more preferably 13 to 16 parts by weight. By including dimethyl sulfoxide in the above weight range, the solubility of flat speed rot in organic solvents can be improved, the stability of the formulation can also be ensured, and the precipitation of the original material at low temperature can be prevented.

In addition, the herbicide composition of the present invention may comprise gamma-butyrolactone and dimethylene in a weight ratio of 3 to 6: 1, or a weight ratio of 3 to 5: 1, or a weight ratio of 3.3 to 4: 1 . If the numerical range is met, the solubility of Ping-Quan rotting in organic solvents can be further improved, which can ensure the stability of the formulation, and can effectively prevent the precipitation of the original material at low temperature, so as to obtain more favorable drug effect performance.

The emulsifier (emulsifier) contained in the herbicide composition of the present invention may be selected from one or more of the group consisting of: anionic (anionic), non-ionic (non-ionic) and cationic (cationic) The emulsifier may particularly include at least one or more selected from the group consisting of: alkylaryl ether sulfate salt, phosphate ester salt, sulfosuccinate ( sulfosuccinate salt), alcohol ether ethoxylate, alcohol ether alkoxylate, alkylphenol ether ethoxylate, alcohol phenol ether alkoxylate , block co-polymer, fatty acid alkoxylate, fatty amine alkoxylate, alkyl polyglucoside, alkoxylated vegetable oil vegetable oil), sorbitol ester alkoxylate, amine oxide, fatty amine alkoxylate, quaternary ammonium salt and ethylene oxide The polymer (oxirane-containing polymer).

For example, the emulsifier may include one or more selected from the group consisting of polyoxyethylene alkyl ether (polyoxyethylene alkyl ether) [RO(CH ₂ CH ₂ O) _m H], fatty acid sorbitol ester ( fatty acid sorbitan ester), fatty acid diethanolamine [RCON(CH ₂ CH ₂ OH) ₂ ], alkyl monoglyceryl ether [ROCH ₂ CH(OH)CH ₂ OH], polyethylene Diol-polypropylene glycol-polyethylene glycol block copolymer (polyethylene glycol-polypropylene glycol-polyethylene glycol block copolymer), and a polymer of 2-methylethylene oxide and ethylene oxide (oxirane, 2-methyl -, polymer with oxirane)[HO(C ₂ H ₄ O) _a (C ₃ H ₆ O) _b (C ₂ H ₄ O) _a H].

For example, polyoxyethylene alkyl ether (polyoxyethylene alkyl ether) may contain one or more selected from the group consisting of: polyoxyethylene lauryl ether (polyoxyethylene lauryl ether), polyoxyethylene tridecyl ether (polyoxyethylene tridecyl ether), polyoxyethylene cetyl ether, polyoxyethylene oleyl ether, polyoxy dodecyl ether, polyoxytetradecyl ether ), and polyoxyhexadecyl ether.

Preferably, the emulsifier may include polyoxyethylene lauryl ether and oxirane, 2-methyl-, polymer with oxirane.

Based on 100 parts by weight of the herbicide composition, it may contain 10 to 45 parts by weight of emulsifier, preferably 12 to 45 parts by weight, or 15 to 45 parts by weight, or 20 to 40 parts by weight, or 25 to 35 parts by weight. By including the emulsifier in this weight range, the emulsion can form a nano-scale droplet size, thus maximizing the foliar penetration effect of flat rot.

The herbicide composition of the present invention has weeding activity against harmful plants. Harmful plants mean unwanted plants that grow in crop arable land and need to be controlled. Weeds are plentiful and can be classified in many ways.

According to the general classification method of weeds, weeds can be divided into Gramineae weeds, Cyperaceae weeds, and broadleaf weeds. Grass weeds include sorghum, barnyard grass, rice cockspur, couch grass, fall panicum, crabgrass, purple crabgrass ( violet crabgrass), wire grass, foxtail, dense-flower bristlegrass, Setaria faberi, Asian sprangletop, multi-stem teff (multi- stem lovegrass), Indian lovegrass, Setaria viridis, hard bluegrass, and bluegrass. Weeds in the Cyperaceae family include galingale, rush-like bulrush, nut grass, tidal-marsh flatsedge, Circaea cordata Royle, East Asian rush (east Asian spikerush), or rush (bulrush). Broadleaf weeds include Sheathed monochoria, Slanum nigrum, or cocklebur.

Furthermore, weeds can be classified into monocotyledonous weeds or dicotyledonous weeds according to the number of leaves. Monocotyledonous weed species may comprise grasses or sedges. Dicotyledonous weed species may include: Asteraceae weeds, including False daisy, Siegesbeckia pubescens makino, Spreading sneezeweed, European yellow Aster (Senecio vulgaris), Mugwort, Frondosa, Teraxacum officinale Weber, Prairie fleabane, colt's-tail, Galinsoga ciliata ), Lyre-shape hemistepta, Shady nipplewort, perennial artemisia, Spanish needles, Hairstalk St. Paul's wort, Hogweed (Ambrosia trifida L.), Leaf Rabbit Lettuce (Ixeris dentata), Korean Lettuce (Korean lettuce), Gooseberry (Indian lettuce), Wild White Peacock Weed (Aster pilosus wild), Cat Thistle (Breea segeta kitamura) , dandelion, hogweed, Jerusalem artichoke, erechtites hieracifolia, etc.; labiatae weeds, including Elsholtzia ciliata, Stachys riederi, Mosia punctulata nakai, motherwort, etc.; Euphorbiaceae weeds, including Asian copperleaf, Eyebane, Euphorbia supina Rafinesque, etc.; Scrophulariaceae weeds, including Asian mazus, Prostrate false pimpemel, etc.; Solanaceae weeds, including Solanum nigrum, Solanum nigrum (American slanum nig rum), etc.; Amaranthaceae weeds (Amaranthaceae weeds), including wild amaranth (wild amaranth), blue amaranth (Speen amaranth), etc.; Oxalidaceae weeds (Oxalidaceae weeds), including wood sorrel (wood sorrel), yellow flower Yellow wood sorrel, etc.; Geraniaceae weeds, including alfilaria, cranesbill, etc.; Malvaceae weeds , including Hibiscus trionum, Indian mallow, etc.; Cannabinaceae weeds, including Japanese hop, hemp, etc.; Onagraceae weeds , including Climbing seedbox, common evening primrose, etc.; Portulacaceae weeds, including purslane, etc.; Equisetaceae weeds, including horsetail etc.; Araceae weeds, including pinellia, etc.; Apiaceae weeds, including hedge parsley, etc.; Aizoaceae weeds, Commelinaceae weeds, including spiderwort, etc.; Crassulaceae weeds, including sedum, etc.; Papaveaceae miscellaneous Papaveraceae weeds, including great celandine, etc.; Asclepiadaceae weeds, including milkweed, etc.; Violaceae weeds, including violet etc.; Caryophyllaceae weeds, including Giant checkweed, etc.; Urticaceae weeds, including Mongolian clearweed, etc.; Boraginaceae weeds, Contains Common Asian trigono tis), etc.; Plantaginaceae weeds, including plantain, etc.; Rosaceae weeds, including Spreading cinquefoil, etc.; and Pontederiaceae weeds ), including Sheathed monochoria and the like.

The following embodiments are proposed to provide a complete disclosure and explanation of how to make and evaluate the compounds, compositions and methods provided in this disclosure, and are provided for illustration purposes only. Accordingly, the embodiments do not limit the scope of the invention as conceived by the inventors of the present invention. Various modifications and combinations of reaction conditions can be made, such as concentrations of constituents, desired solvents, solvent mixtures, temperature, pressure, and other reaction parameters, as well as conditions to optimize product properties such as purity and yield. Rate). Such modifications are also considered to be within the scope of this disclosure. Any combination of the above-explained elements in all possible variations is encompassed by the invention unless otherwise expressly stated or expressly denied in this disclosure.

Experimental example 1 : Evaluation of dissolution stability 1

2.12 g of flat speed rot and 67.88 g of each solvent according to Table 1 were mixed and stirred using a stirrer at 50° C. at 400 rpm and checked for dissolution. Afterwards, the mixture was stored at low temperature (0° C.) for two weeks, and checked whether the raw material precipitated to evaluate dissolution stability.

As shown in Table 1 above, the flat-speed rotten raw material is easily soluble in γ-butyrolactone, and no precipitation is found after storage at low temperature, thus confirming the composition of the herbicide comprising γ-butyrolactone as an organic solvent according to the present invention exhibited excellent formulation stability.

And, as shown in Table 1, in the case of other well-known solvents other than γ-butyrolactone, PBS is not easily soluble and precipitates after storage at low temperature, thus showing poor formulation stability. In addition, in the case of NMP, it dissolves quickly and quickly, but precipitates are found after storage at low temperature, which confirms that the stability of the formulation is not good.

Experimental example 2 : Solubility Evaluation II

For the use of a mixture of γ-butyrolactone and dimethyl oxide as an organic solvent, the solubility and stability of the formulation were confirmed.

Specifically, flat speed rotten, γ-butyrolactone, and dimethyl oxide were mixed in the amounts shown in Table 2 below, and stirred with a stirrer at 50° C. at 400 rpm to prepare Preparation Examples 1 to 4, and Reference The composition of Example 1, and then visually confirm whether the flat speed rot is dissolved.

As shown in the above Table 2, it can be confirmed that, compared to Preparation Example 1 and Preparation Example 2 using only γ-butyrolactone as an organic solvent, in the case of using γ-butyrolactone and dimethyloxide together as an organic solvent, the It is easy to dissolve a large amount of flat and fast rot. From this, it was confirmed that the solubility of Pyramid was further improved in the case of using a mixture of γ-butyrolactone and dimethyl oxide compared to the case of using γ-butyrolactone alone as an organic solvent.

And, although the results are not recorded in Table 2, in the case of using only γ-butyrolactone as an organic solvent and using 10 parts by weight of flat speed rot, the flat speed rot was not completely dissolved. In addition, it can be confirmed from Reference Example 1 that although γ-butyrolactone and dimethyl oxide are mixed and used as an organic solvent to improve the solubility of flat quick rot, if 100 parts by weight of the total composition is used as a basis When 15 parts by weight of flat speed rotten, the dissolution will not be easy to carry out. It can thus be expected that in the case of containing a fixed amount of flat fast rot, such as more than 12.5 parts by weight, the solubility will be poor, and the stability of the formulation will be reduced, and therefore, the drug effect will be reduced.

Example 1

2 g of flat speed rot and 68 g of γ-butyrolactone were mixed and stirred using a stirrer at 50° C. at 400 rpm to dissolve. After the dissolution was confirmed visually, the heating was stopped, and a total of 30 g of emulsifier polyoxyethylene lauryl ether (polyoxyethylene lauryl ether) and a polymer of 2-methyloxirane and oxirane (oxirane) were injected. , 2-methyl-, polymer with oxirane), and then fully stirred with a stirrer at 400 rpm to prepare the herbicide composition of the emulsion (EC) formulation.

Example 2

2 g of flat speed rot was mixed with 51 g of γ-butyrolactone and 17 g of dimethyl ethylene oxide, and then stirred at 50° C. at 400 rpm using a stirrer to dissolve. After the dissolution was confirmed visually, the heating was stopped, and a total of 30 g of emulsifier polyoxyethylene lauryl ether (polyoxyethylene lauryl ether) and a polymer of 2-methyloxirane and oxirane (oxirane) were injected. , 2-methyl-, polymer with oxirane), and then fully stirred with a stirrer at 400 rpm to prepare the herbicide composition of the emulsion (EC) formulation.

Example 3

2 g of flat speed ketone was mixed with 58.3 g of γ-butyrolactone and 9.7 g of dimethyloxide, and then stirred at 50° C. at 400 rpm using a stirrer to dissolve. After the dissolution was confirmed visually, the heating was stopped, and a total of 30 g of emulsifier polyoxyethylene lauryl ether (polyoxyethylene lauryl ether) and a polymer of 2-methyloxirane and oxirane (oxirane) were injected. , 2-methyl-, polymer with oxirane), and then fully stirred with a stirrer at 400 rpm to prepare the herbicide composition of the emulsion (EC) formulation.

comparative example 1

A penoxsulam single formulation (product name: Salchodaecheop) with a liquid phase suspension concentrate (SC) formulation containing 3 g of penoxsulam was prepared.

Experimental example 3 : Evaluation of Drug Effects

The herbicide compositions of Examples 1 to 3 and Comparative Example 1 were used to evaluate the drug effect of weeding. Specifically, the target weeds are rice cockspur (resistance, sensitivity) and water clove (Climbing seedbox) with 3-4 leaves, and the growth time of weeds during the treatment For about 4 leaves. The amount of water used to dilute the product is based on 300 L/ha, and the amount of active ingredient (penoxsulam) in the herbicide composition is 20 g a.i./ha.

The research method included visual comparison with the control group without drug treatment on the 11th day and 23rd day after the drug treatment, and the evaluation of the herbicidal activity according to the following evaluation criteria. The results are shown in Table 3 below. Before and after treatment, as for port management, foliage treatment was carried out after complete drainage, and a submerged depth of 1 cm was maintained after 24 hours of treatment.

Evaluation criteria: 0 (not controlled) -> 100 (completely controlled)

Referring to the above Table 3, it can be confirmed that, when compared with the herbicide composition of Comparative Example 1, the herbicide compositions of Examples 1 to 3 show the same or better herbicidal activity.

In addition, in the case of Example 2 and Example 3, when compared with Example 1 and Comparative Example 1, the herbicidal activity against rice barnyardgrass (resistant) and water lilac (sensitivity) was faster and better.

Moreover, as confirmed in the above Table 1, in the case of other solvents, Pyramid was not dissolved, and the stability of the formulation was not good, so it showed no herbicidal drug effect.

Furthermore, Comparative Example 1 is a common herbicide composition with excellent effect. As confirmed in Table 3 above, when compared with Comparative Example 1, the herbicide composition according to the present invention shows the same or better herbicidal effect. It can be seen that the present invention has the effect of providing a herbicide composition having excellent effects as other formulations.

Claims (10)

A herbicide composition comprising penoxsulam, an organic solvent and an emulsifier, Wherein, the organic solvent contains gamma-butyrolactone (gamma-butyrolactone). The herbicide composition according to claim 1, wherein the herbicide composition has an emulsifiable concentrate (EC) formulation. The herbicide composition according to claim 1, wherein, based on 100 parts by weight of the herbicide composition, it contains 0.1 to 13.5 parts by weight of smooth rot. The herbicide composition according to claim 1, wherein, based on 100 parts by weight of the herbicide composition, it contains 50 to 99 parts by weight of γ-butyrolactone. The herbicide composition according to claim 1, wherein the organic solvent further comprises dimethyl sulfone. The herbicide composition according to claim 5, wherein, based on 100 parts by weight of the herbicide composition, it contains 4 to 25 parts by weight of dimethyl ethylene oxide. The herbicide composition according to claim 5, wherein the weight ratio of γ-butyrolactone and dimethyloxide is 3 to 6:1. The herbicide composition as claimed in claim 1, wherein the emulsifier comprises at least one or more selected from the group consisting of: alkylaryl ether sulfate salt (alkylaryl ether sulfate salt), phosphate ester salt ( phosphate ester salt, sulfosuccinate salt, alcohol ether ethoxylate, alcohol ether alkoxylate, alkylphenol ether ethoxylate, alcohol Alcoholphenol ether alkoxylate, block copolymer, fatty acid alkoxylate, fatty amine alkoxylate, alkyl polyglucoside, alkoxy Alkoxylated vegetable oil, sorbitol ester alkoxylate, amine oxide, fatty amine alkoxylate, quaternary ammonium salt and ethylene oxide containing Polymer (oxirane-containing polymer). As the herbicide composition of claim 1, wherein the emulsifier comprises polyoxyethylene lauryl ether (polyoxyethylene lauryl ether) and a polymer of 2-methyloxirane and oxirane (oxirane, 2-methyl- , polymer with oxirane). The herbicide composition according to claim 1, wherein, based on 100 parts by weight of the herbicide composition, it contains 10 to 45 parts by weight of the emulsifier.