在作物種植情形下，重要的是藉由控制會抑制作物生長之雜草來保護作物。為了減少種植區域內的雜草生長所引起之損害比如作物生長或產量的損失，能夠有效地控制雜草並對作物是安全的活性除草物質已經被開發。迄今為止所開發之許多活性除草物質已經以特異作物登記並用於雜草控制。用於控制在特異作物的種植區域內之雜草生長的這樣之除草活性物質優選為具有高除草活性與廣泛除草廣效性且優選為對環境與作物安全。
同時，包括這樣的活性除草物質之除草組成物已經被開發並用於調配物，比如可濕性粉劑、可乳化濃縮物、水分散性粒劑、粒劑、懸浮濃縮物等。然而，在一般用水稀釋成預定濃度以製備可噴霧溶液的可濕性粉劑、可乳化濃縮物、與水分散性粒劑情況下，對均勻地噴灑在目標稻田或田野之整個表面上有昂貴且費時的問題。儘管可濕性粉劑、可乳化濃縮物、與水分散性粒劑之問題可以用能夠直接被使用而不用水稀釋的粒劑來解決，然而這樣之粒劑包括以除草劑總量為基準計相對低含量的活性除草物質，必須包括用於形成除草劑之助劑，係藉由包括粉碎、混合、研磨、粒化、乾燥、分級等的複合程序來製得，並有比如由於噴霧導致斑出現之問題。為了解決這樣的問題，已經開發懸浮濃縮物調配物，其之製造程序相對簡單且環保並允許簡單與高效率噴灑。同時，在利用這樣的各種除草劑調配物時，重要的是即使在長期儲存時，也能保障這些除草組成物之穩定性。
下列化學式a所示之化合物[提議的ISO名稱：氟吡磺隆(flucetosulfuron)]，其係屬於磺醯脲類之活性除草物質，已經在韓國專利號10-0399366(韓國專利申請號
10-2000-0059990)中被提議為活性除草物質：
已知氟吡磺隆在土壤或葉片處理時對米、小麥、大麥(適當劑量：10至40 g a.i./ha)、與草(適當劑量：50至200 g a.i./ha)是安全的並對各種雜草類型比如闊葉雜草、禾本科雜草、莎草科雜草、一年生雜草、與多年生雜草發揮極佳之除草效果。
然而，在保障包括這樣的磺醯脲類之活性除草物質的除草組成物之穩定性方面仍有一個問題。特別地，由於當在高溫下儲存時懸浮濃縮物(SC)調配物的穩定性因為水解而進一步惡化，所以很難長期儲存該SC調配物。[ 相關技術文件 ] [ 專利文件 ]
韓國專利號10-0399366In the case of crop planting, it is important to protect the crop by controlling weeds that inhibit the growth of the crop. In order to reduce the damage caused by the growth of weeds in the planting area, such as crop growth or yield loss, active herbicides that can effectively control weeds and are safe for crops have been developed. Many active herbicidal substances developed so far have been registered as specific crops and used for weed control. Such herbicidal active substances for controlling the growth of weeds in the planting area of specific crops preferably have high herbicidal activity and wide herbicidal versatility, and are preferably safe for the environment and crops. At the same time, herbicidal compositions including such active herbicidal substances have been developed and used in formulations, such as wettable powders, emulsifiable concentrates, water-dispersible granules, granules, suspension concentrates, and the like. However, in the case of wettable powders, emulsifiable concentrates, and water-dispersible granules that are generally diluted with water to a predetermined concentration to prepare a sprayable solution, it is expensive and expensive to spray uniformly on the entire surface of the target rice field or field. Time-consuming question. Although the problems of wettable powders, emulsifiable concentrates, and water-dispersible granules can be solved by granules that can be used directly without diluting with water, such granules include the relative amount of herbicides. Low-content active herbicidal substances must include additives for the formation of herbicides, which are prepared by a compound process including pulverization, mixing, grinding, granulation, drying, classification, etc., and for example, the appearance of spots due to spraying The problem. In order to solve such problems, suspension concentrate formulations have been developed, the manufacturing process of which is relatively simple and environmentally friendly and allows simple and efficient spraying. At the same time, when using such various herbicide formulations, it is important to ensure the stability of these herbicidal compositions even during long-term storage. The compound represented by the following chemical formula a [Proposed ISO name: flucetosulfuron (flucetosulfuron)], which belongs to the active herbicide of sulfonylurea, has been listed in Korean Patent No. 10-0399366 (Korean Patent Application No. 10-2000 -0059990) is proposed as an active herbicide: It is known that flupisulfuron-methyl is safe for rice, wheat, barley (appropriate dose: 10 to 40 g ai/ha), and grass (appropriate dose: 50 to 200 g ai/ha) in soil or leaf treatments. Various weed types such as broadleaf weeds, gramineous weeds, cyperaceae weeds, annual weeds, and perennial weeds have excellent weeding effects. However, there is still a problem in ensuring the stability of herbicidal compositions including such active herbicidal substances such as sulfonylureas. In particular, since the stability of the suspension concentrate (SC) formulation is further deteriorated due to hydrolysis when stored at a high temperature, it is difficult to store the SC formulation for a long time. [ Related Technical Documents ] [ Patent Documents ] Korean Patent No. 10-0399366
[ 技術問題 ]
因此，本發明係鑒於上述問題完成，並且本發明之一個目的是提供包括屬於磺醯脲類之活性除草物質的除草組成物，該除草組成物具有極佳穩定性連同極佳除草活性，從而能夠長期儲存。[ 技術方案 ]
本發明之一個態樣提供除草組成物，其包括作為活性成分的下式1所示之吡啶磺醯脲化合物，該吡啶磺醯脲化合物是包括赤型(erythro form)與蘇型的異構物混合物，該異構物混合物包括92重量%或更多之赤型：
其中n代表1至3的整數，R是氫原子或C1至C4烷基，R'是氫原子、C1至C4烷基、C1至C3鹵烷基、鹵素基、或C1至C2烷氧基，及X與Y各獨立地是C1至C2烷基、C1至C2烷氧基、C1至C2鹵烷氧基、或鹵素基。[ 有利功效 ]
根據本發明，能提供除草組成物，其即使在高溫下長期儲存時也具有極佳除草活性與低分解速率，特別地，甚至在懸浮濃縮物(SC)調配物中也具有極佳穩定性。[ 本發明之模式 ]
現在，將更詳細描述本發明以助於了解本發明。在本說明書與隨附申請專利範圍中所用之用語或字詞不應受限於通用意義或字典意義，並且具有對應於本發明的實施方式之技術態樣的意義與概念，以便最適當地表達本發明之實施方式。
本發明之除草組成物包括作為活性成分的下式1所示之吡啶磺醯脲化合物，該吡啶磺醯脲化合物是包括赤型與蘇型的異構物混合物，該異構物混合物包括92重量%或更多之赤型：
其中n代表1至3的整數，R是氫原子或C1至C4烷基，R'是氫原子、C1至C4烷基、C1至C3鹵烷基、鹵素基、或C1至C2烷氧基，及X與Y各獨立地是C1至C2烷基、C1至C2烷氧基、C1至C2鹵烷氧基、或鹵素基。
更佳地，在式1中，n可為1或2的整數，R可為氫原子或甲基，R'可為氫原子、鹵素基、或甲基，及X與Y可各為甲氧基。
甚至更佳地，在式1中，n可為1或2的整數，R可為甲基，R'可為氫原子、Cl、Br、或甲基，及X與Y可各為甲氧基。
式1所示之吡啶磺醯脲化合物可為例如選自由下列所組成之組群中的至少一者：N-[(4,6-二甲氧基嘧啶-2-基)胺基羰基]-2-(2-氟-1-甲氧基乙醯氧基-正丙基)吡啶-3-磺醯胺、N-[(4,6-二甲氧基嘧啶-2-基)胺基羰基]-2-(2-氟-1-羥基乙醯氧基-正丙基)吡啶-3-磺醯胺、N-[(4,6-二甲氧基嘧啶-2-基)胺基羰基]-2-(2-氟-1-(3-羥基丙醯)氧基-正丙基)吡啶-3-磺醯胺、N-[(4,6-二甲氧基嘧啶-2-基)胺基羰基]-2-(2-氟-1-(3-甲氧基丙醯)氧基-正丙基)吡啶-3-磺醯胺、N-[(4,6-二甲氧基嘧啶-2-基)胺基羰基]-4-甲基-2-(2-氟-1-甲氧基乙醯氧基-正丙基)吡啶-3-磺醯胺、N-[(4,6-二甲氧基嘧啶-2-基)胺基羰基]-4-氯-2-(2-氟-1-甲氧基乙醯氧基-正丙基)吡啶-3-磺醯胺、及N-[(4,6-二甲氧基嘧啶-2-基)胺基羰基]-4-溴-2-(2-氟-1-甲氧基乙醯氧基-正丙基)吡啶-3-磺醯胺。
更佳地，式1所示之吡啶磺醯脲化合物可為下式2所示之化合物[提議的ISO名稱：氟吡磺隆(flucetosulfuron)]：
由於式1所示之化合物包括二個不對稱碳，該化合物可能以赤型異構物或蘇型異構物形式存在。
本發明之除草組成物包括為異構物混合物(包括赤型與蘇型)之式1所示的化合物。在這裡，包括以該異構物混合物總量為基準計92重量%或更多之量的赤型。更佳地，可包括以該異構物混合物總量為基準計95重量%或更多之量的赤型。甚至更佳地，可包括以該異構物混合物總量為基準計95重量%至99重量%之量的赤型。
由於包括以該異構物混合物(包括赤型與蘇型)總量為基準計92重量%或更多之量的赤型，所以展現出極佳除草活性，且即使在高溫下長期儲存時由於低分解速率而保障穩定性。
當只包括式1所示之化合物的赤型時，生產效率大減。當只包括式1所示之化合物的蘇型時，除草活性減少，而分解速率大增，其導致穩定性降低。此外，當式1所示之化合物是為異構物混合物(包括赤型與蘇型)形式存在，但在該異構物混合物中的赤型含量少於92重量%時，除草活性減少，而分解速率增加。特別地，在液態調配物情況下，由於水解使其穩定性進一步減少，據此很難在高溫下長期儲存。
在本發明中，包括式1所示之化合物的異構物混合物之除草組成物可能以通用除草組成物調配物形式使用。包括該異構物混合物的除草組成物可能另外包括載體、界面活性劑、或添加劑(一般用於調配物領域者，根據需要)，並可能以各種調配物形式利用。該載體與添加劑中之每一者可能是固體或液體，特別是用於調配物領域的有用成分，例如天然或合成無機物質、溶劑、分散劑、潤濕劑、黏著劑、增稠劑、黏合劑等。
例如，該除草組成物可被製備成至少一種選自由下列所組成之組群中的調配物：懸浮濃縮物、擴散油、可濕性粉劑、水分散性粒劑、分散性粉劑、散布劑、丸劑、粒劑、及錠劑。更佳地，該除草組成物可為懸浮濃縮物。當該除草組成物是懸浮濃縮物時，該除草組成物可能另外包括緩衝劑、界面活性劑、與抗凍摻合物。在懸浮濃縮物情況下，其製造程序相對簡單，對生態環境友善，且對噴灑之而言簡單且高效率，但其穩定性由於水解所引起之分解而減少。然而，由於在本發明的除草組成物之異構物混合物(包括赤型與蘇型)中包括92重量%或更多的量之赤型，所以穩定性大增。因此，由於這樣的懸浮濃縮物調配物水解所引起之分解減少且可以在高溫下長期儲存。
該除草組成物可被製備成各種調配物，例如利用根據已知方法混合與/或粉碎有效成分與溶劑、固體載體、界面活性劑或其他添加劑。
下列物質可作為溶劑：芳烴類，例如二甲苯混合物或經取代萘；醇類與二醇類，比如乙醇、乙二醇、乙二醇一甲醚、或乙二醇一乙醚及其醚類與酯類；酮類，比如環己酮；強極性溶劑，比如N-甲基-2-吡咯啶酮、二甲亞碸、與二甲基甲醯胺；及環氧化或未環氧化植物油，比如環氧化椰子油與大豆油；或水。這樣的溶劑可作為用於液態調配物之溶劑或用於粒狀調配物的共溶劑。
作為一般用於散布劑與粒狀調配物之固體載體的例子，有經粉碎之天然礦物，比如滑石、高嶺土、蒙脫石、葉蠟石、膨土、與碳酸鈣、吸收劑載體，比如沸石、與砂。此外，可使用各種預粉碎的無機材料或有機材料。
上述界面活性劑可能選自非離子、陽離子與/或陰離子界面活性劑，其展現出令人滿意之分散、潤濕、與潤滑特性，取決於待調配的式1所示之化合物的性質。
就投予包括式1所示之化合物的異構物混合物之除草組成物的更佳方法而論，有用液態調配物潤濕植物棲地的方法或把固態形式(例如粒狀調配物形式)之活性成分加到土壤(土壤處理)中以透過土壤或水透過根與莖到達植物。或者，可藉由直接投予植物的葉(葉片應用)來展現出組成物之除草活性。投予的頻率與速率可根據植物、氣候、與土壤環境之生物特性而不同。
以下，將說明本發明之具體實施方式。然而，應當理解該實施方式並非提供來限制本發明的範圍且在隨附申請專利範圍之範圍中的所有替代件與修改件皆包括在本發明中。因此，為說明起見將仔細地說明下列具體實施方式，並且為容易了解起見將提供方法與態樣。
只為說明起見而提供下列實施例來向該領域之具有普通技藝者說明所提供的化合物、組成物、與方法如何製造與評估。因此，下列實施例無意限制發明者認為是本發明之範圍。有許多可用於使下列優化的條件之變型與組合：反應條件、成分濃度、所欲溶劑、溶劑混合物、溫度、壓力、其他反應參數、與產物性質比如純度與產率。這些被認為包括在本發明的範圍中。所有可能之變型的任何組合包括在本發明之範圍中，除非在本文中另外指出或除非與上下文明顯地相矛盾。 [ Technical Problem ] Therefore, the present invention was completed in view of the above-mentioned problems, and an object of the present invention is to provide a herbicidal composition including active herbicidal substances belonging to the sulfonylureas, which has excellent stability and excellent herbicidal properties. Active, which can be stored for a long time. [ Technical Solution ] One aspect of the present invention provides a herbicidal composition, which includes as an active ingredient a pyridine sulfonylurea compound represented by the following formula 1. The pyridine sulfonylurea compound includes erythro form and threo form A mixture of isomers, the mixture of isomers includes 92% by weight or more of the red form: Where n represents an integer from 1 to 3, R is a hydrogen atom or a C1 to C4 alkyl group, R'is a hydrogen atom, a C1 to C4 alkyl group, a C1 to C3 haloalkyl group, a halogen group, or a C1 to C2 alkoxy group, And X and Y are each independently a C1 to C2 alkyl group, a C1 to C2 alkoxy group, a C1 to C2 haloalkoxy group, or a halogen group. [ Advantageous effect ] According to the present invention, it is possible to provide a herbicidal composition which has excellent herbicidal activity and low decomposition rate even when stored for a long time at a high temperature, and in particular, has excellent herbicidal activity even in a suspension concentrate (SC) formulation. Good stability. [ Modes of the present invention ] Now, the present invention will be described in more detail to help understand the present invention. The terms or words used in the scope of this specification and the appended application should not be limited to general meanings or dictionary meanings, and have meanings and concepts corresponding to the technical aspects of the embodiments of the present invention, so as to most appropriately express the text. The embodiment of the invention. The herbicidal composition of the present invention includes as an active ingredient a pyridine sulfonylurea compound represented by the following formula 1. The pyridine sulfonylurea compound is a mixture of isomers including erythro-form and threo-form, and the isomer mixture includes 92 weights % Or more red type: Where n represents an integer from 1 to 3, R is a hydrogen atom or a C1 to C4 alkyl group, R'is a hydrogen atom, a C1 to C4 alkyl group, a C1 to C3 haloalkyl group, a halogen group, or a C1 to C2 alkoxy group, And X and Y are each independently a C1 to C2 alkyl group, a C1 to C2 alkoxy group, a C1 to C2 haloalkoxy group, or a halogen group. More preferably, in Formula 1, n can be an integer of 1 or 2, R can be a hydrogen atom or a methyl group, R'can be a hydrogen atom, a halogen group, or a methyl group, and X and Y can each be methoxy base. Even more preferably, in formula 1, n can be an integer of 1 or 2, R can be a methyl group, R'can be a hydrogen atom, Cl, Br, or a methyl group, and X and Y can each be a methoxy group . The pyridine sulfonylurea compound represented by formula 1 can be, for example, at least one selected from the group consisting of: 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-hydroxypropionyl)oxy-n-propyl)pyridine-3-sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl )Aminocarbonyl)-2-(2-fluoro-1-(3-methoxypropionyl)oxy-n-propyl)pyridine-3-sulfonamide, N-((4,6-dimethoxy Pyrimidin-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-sulfonyl Amine, and N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-4-bromo-2-(2-fluoro-1-methoxyacetoxy-n-propyl ) Pyridine-3-sulfonamide. More preferably, the pyridine sulfonylurea compound represented by formula 1 may be the compound represented by formula 2 below [Proposed ISO name: flucetosulfuron (flucetosulfuron)]: Since the compound represented by formula 1 includes two asymmetric carbons, the compound may exist in the form of erythro isomer or threo isomer. The herbicidal composition of the present invention includes the compound represented by Formula 1 which is a mixture of isomers (including erythro-type and threo-type). Here, an amount of 92% by weight or more based on the total amount of the isomer mixture is included. More preferably, the erythroform may be included in an amount of 95% by weight or more based on the total amount of the isomer mixture. Even more preferably, the red form may be included in an amount of 95% to 99% by weight based on the total amount of the isomer mixture. Since it includes 92% by weight or more of the red form based on the total amount of the isomer mixture (including the red form and threo form), it exhibits excellent herbicidal activity, and it exhibits excellent herbicidal activity even when stored for a long time at a high temperature. Low decomposition rate to ensure stability. When only the red form of the compound represented by formula 1 is included, the production efficiency is greatly reduced. When only the threo type of the compound represented by formula 1 is included, the herbicidal activity is reduced, and the decomposition rate is greatly increased, which leads to a decrease in stability. In addition, when the compound represented by Formula 1 exists in the form of a mixture of isomers (including erythro-type and threo-type), but the erythro-type content in the isomer mixture is less than 92% by weight, the herbicidal activity decreases, and The decomposition rate increases. In particular, in the case of a liquid formulation, its stability is further reduced due to hydrolysis, which makes it difficult to store it at high temperatures for a long time. In the present invention, the herbicidal composition including a mixture of isomers of the compound represented by Formula 1 may be used in the form of a general herbicidal composition formulation. The herbicidal composition including the mixture of isomers may additionally include a carrier, a surfactant, or an additive (generally used in the field of formulations, as required), and may be used in the form of various formulations. Each of the carrier and additives may be solid or liquid, especially useful ingredients used in the field of formulations, such as natural or synthetic inorganic substances, solvents, dispersants, wetting agents, adhesives, thickeners, and adhesives剂 etc. For example, the herbicidal composition can be prepared into at least one formulation selected from the group consisting of suspension concentrates, diffusing oils, wettable powders, water-dispersible granules, dispersible powders, spreading agents, Pills, granules, and lozenges. More preferably, the herbicidal composition may be a suspension concentrate. When the herbicidal composition is a suspension concentrate, the herbicidal composition may additionally include a buffer, a surfactant, and an antifreeze blend. In the case of suspension concentrates, its manufacturing process is relatively simple, friendly to the ecological environment, and simple and efficient for spraying, but its stability is reduced due to decomposition caused by hydrolysis. However, since the erythroform is included in an amount of 92% by weight or more in the isomer mixture (including the red form and threo form) of the herbicidal composition of the present invention, the stability is greatly increased. Therefore, the decomposition caused by the hydrolysis of such suspension concentrate formulations is reduced and can be stored at high temperatures for a long time. The herbicidal composition can be prepared into various formulations, for example, by mixing and/or pulverizing active ingredients with solvents, solid carriers, surfactants or other additives according to known methods. The following substances can be used as solvents: aromatic hydrocarbons, such as xylene mixtures or substituted naphthalenes; alcohols and glycols, such as ethanol, ethylene glycol, ethylene glycol monomethyl ether, or ethylene glycol monoethyl ether and its ethers Esters; ketones, such as cyclohexanone; strong polar solvents, such as N-methyl-2-pyrrolidone, dimethylsulfoxide, and dimethylformamide; and epoxidized or unepoxidized vegetable oils, such as Epoxidized coconut oil and soybean oil; or water. Such solvents can be used as solvents for liquid formulations or as co-solvents for granular formulations. As examples of solid carriers generally used for dispersing agents and granular formulations, there are pulverized natural minerals, such as talc, kaolin, montmorillonite, pyrophyllite, bentonite, and calcium carbonate, and absorbent carriers, such as zeolite , And sand. In addition, various pre-pulverized inorganic materials or organic materials can be used. The aforementioned surfactants may be selected from nonionic, cationic and/or anionic surfactants, which exhibit satisfactory dispersion, wetting, and lubricating properties, depending on the properties of the compound represented by Formula 1 to be formulated. Regarding the better method of administering the herbicidal composition comprising the isomeric mixture of the compound represented by formula 1, the method of wetting the plant habitat with the liquid formulation or the solid form (such as the granular formulation) The active ingredient is added to the soil (soil treatment) to reach the plant through the soil or water through the roots and stems. Alternatively, the herbicidal activity of the composition can be exhibited by directly administering to the leaves of the plant (leaf application). The frequency and rate of administration may vary according to the biological characteristics of plants, climate, and soil environment. Hereinafter, specific embodiments of the present invention will be described. However, it should be understood that this embodiment is not provided to limit the scope of the present invention and all alternatives and modifications within the scope of the appended patent application are included in the present invention. Therefore, for the sake of explanation, the following specific embodiments will be explained carefully, and methods and aspects will be provided for the sake of easy understanding. The following examples are provided for illustrative purposes only to illustrate how the provided compounds, compositions, and methods are manufactured and evaluated to those of ordinary skill in the field. Therefore, the following examples are not intended to limit the scope of the present invention considered by the inventors. There are many variations and combinations that can be used to optimize the following conditions: reaction conditions, component concentrations, desired solvents, solvent mixtures, temperature, pressure, other reaction parameters, and product properties such as purity and yield. These are considered to be included in the scope of the present invention. Any combination of all possible variations is included in the scope of the present invention, unless otherwise indicated herein or unless it is clearly contradictory to the context.
實施例 1
將水加到K2
HPO4
與KH2
PO4
以製備總共1 L之溶液，藉此製備0.1 M磷酸鹽緩衝劑。其次，把3.0重量份的CR-DOS70P(二(2-乙基己基)磺琥珀酸鹽，鈉鹽，Cas No. 577-11-7)、1.0重量份之NK-SU500 (蔗糖十二烷酸酯，Cas No. 25339-99-5)、與0.2重量份的作為消泡劑之SAG-622(由Momentive製造)加到65.8重量份的緩衝劑，接著充分混合。在均勻混合狀態下，將10.0重量份的包括96重量%之1-(3-{[(4,6-二甲氧基-嘧啶-2-基)胺甲醯基]胺磺醯基}-2-吡啶基)-2-氟丙基甲氧基乙酸酯(氟吡磺隆(flucetosulfuron)
，FTS)的赤型與4重量%之其蘇型之異構物混合物加到該混合物，接著用攪拌器充分混合。把玻璃珠加到所得混合物以進行粉碎。進行此粉碎直到平均粒徑達到1至2 µm。從而，製備好濕部分。
其次，將0.1重量份之X.G(三仙膠，Cas No. 11138-66-2)與0.2重量份的M.V [5-氯-2-甲基-4-異噻唑啉-3-酮(Cas No. 26172-55-4)與2-甲基-4-異噻唑啉-3-酮(Cas No. 2682-20-4)]加到3.0重量份之P.G(丙二醇，Cas No. 57-55-6)，接著在攪拌下充分混合。其次，加入16.7重量份的0.1 M磷酸鹽緩衝劑，接著在攪拌下充分混合。從而，製備好稠化部分。
其次，把30重量份之稠化部分加到70重量份的濕部分，接著在攪拌下充分混合。從而，製備好具有懸浮濃縮物調配物之除草組成物。實施例 2
以同於實施例1中之方式製備具有懸浮濃縮物調配物的除草組成物，但是使用包括92重量%之FTS的赤型與8重量%之其蘇型之異構物混合物。實施例 3
在20重量份之Celite 281 (煅燒矽藻土，Cas No. 91053-39-3)上吸附15重量份的CR-PE62 (聚乙二醇聚丙二醇共聚物，Cas No. 9003-11-6)，然後混合10重量份之包括96重量%的1-(3-{[(4,6-二甲氧基-嘧啶-2-基)胺甲醯基]胺磺醯基}-2-吡啶基)-2-氟丙基甲氧基乙酸酯(氟吡磺隆，FTS)之赤型與4重量%之其蘇型的異構物混合物、2重量份之NK-EFW(2-萘磺酸，具甲醛的聚合物，鈉鹽，Cas No. 36290-04-7)、3重量份之NK-D425 (2-萘磺酸，具甲醛的聚合物，鈉鹽，Cas No. 36290-04-7)、1重量份之CR-SDS(十二烷基硫酸鈉，Cas No. 151-21-3)、與10重量份的CR-UF100F(脲-甲醛樹脂(CAS no.9011-05-6))。其次，混合作為剩餘部分之滑石以使得組成物總量為100重量份，接著使用空氣噴射磨機粉碎。將10至12重量份的水加到經粉碎之混合物，接著捏和，使用造粒機造粒，然後在約80℃下熱風乾燥。從而，製備好具有水分散性粒劑調配物的除草組成物。比較例 1
以同於實施例1中之方式製備具有懸浮濃縮物調配物的除草組成物，但是使用包括88重量%之FTS的赤型與12重量%之其蘇型之異構物混合物。比較例 2
以同於實施例1中之方式製備具有懸浮濃縮物調配物的除草組成物，但是使用包括85重量%之FTS的赤型與15重量%之其蘇型之異構物混合物。比較例 3
以同於實施例3中之方式製備具有水分散性粒劑調配物的除草組成物，但是使用包括88重量%之FTS的赤型與12重量%之其蘇型之異構物混合物。[ 實驗例：除草組成物之儲存穩定性的評估 ]
為評估實施例1至3與比較例1至3之除草組成物的儲存穩定性，在用聚乙烯(PE)製成之塑膠瓶中填充約100 g的液體樣本各者，及在銀箔包封填充粒狀樣本，接著密封。其次，將包封各者在保持於54(±2)℃的烘箱中儲存4週，然後使用HPLC(由Waters製造)測量活性成分之面積值以評估分解速率。結果概述在下表1中。
HPLC分析條件如下：
管柱：100 mm×4.6 mm內徑“Capcell Pak” C18管柱，3 µm粒子
移動相：乙腈/水(0.02 M乙酸銨+0.1 M乙酸) = 32/68
流率：1.0 mL/分。
管柱溫度：30℃
注射體積：10 µl
檢測器波長：254 nm
操作時間：20分。 Example 1 Water was added to K 2 HPO 4 and KH 2 PO 4 to prepare a total of 1 L of solution, thereby preparing a 0.1 M phosphate buffer. Secondly, 3.0 parts by weight of CR-DOS70P (bis(2-ethylhexyl) sulfosuccinate, sodium salt, Cas No. 577-11-7), 1.0 parts by weight of NK-SU500 (sucrose dodecanoic acid Ester, Cas No. 25339-99-5), and 0.2 parts by weight of SAG-622 (manufactured by Momentive) as a defoaming agent were added to 65.8 parts by weight of buffer, and then thoroughly mixed. In a uniformly mixed state, 10.0 parts by weight including 96% by weight of 1-(3-{[(4,6-dimethoxy-pyrimidin-2-yl)aminomethanyl]sulfonamide}- 2-pyridyl)-2-fluoropropyl methoxyacetate (flucetosulfuron (flucetosulfuron, FTS) erythro-form and 4% by weight of its threo-form isomer mixture were added to the mixture, and then Mix thoroughly with a stirrer. Glass beads are added to the resultant mixture for pulverization. Perform this pulverization until the average particle size reaches 1 to 2 µm. Thus, the wet part is prepared. Next, 0.1 parts by weight of XG (Sanxian Gum, Cas No. 11138-66-2) and 0.2 parts by weight of MV [5-chloro-2-methyl-4-isothiazolin-3-one (Cas No. 11138-66-2) 26172-55-4) and 2-methyl-4-isothiazolin-3-one (Cas No. 2682-20-4)] added to 3.0 parts by weight of PG (propylene glycol, Cas No. 57-55- 6), then mix thoroughly under stirring. Secondly, 16.7 parts by weight of 0.1 M phosphate buffer was added, and then mixed thoroughly under stirring. Thus, the thickened part is prepared. Next, add 30 parts by weight of the thickened part to 70 parts by weight of the wet part, and then mix thoroughly with stirring. Thus, the herbicidal composition with the suspension concentrate formulation is prepared. Example 2 prepared a herbicidal composition with a suspension concentrate formulation in the same manner as in Example 1, but used a mixture of erythro-forms including 92% by weight of FTS and 8% by weight of threo-type isomers. Example 3 15 parts by weight of CR-PE62 (polyethylene glycol polypropylene glycol copolymer, Cas No. 9003-11) were adsorbed on 20 parts by weight of Celite 281 (calcined diatomaceous earth, Cas No. 91053-39-3) -6), and then mix 10 parts by weight including 96% by weight of 1-(3-{[(4,6-dimethoxy-pyrimidin-2-yl)aminomethanyl]sulfamoyl}-2 -Pyridyl)-2-fluoropropyl methoxyacetate (flupisulfuron, FTS) is a mixture of the erythro-form and 4% by weight of its threo-form isomer, 2 parts by weight of NK-EFW (2 -Naphthalenesulfonic acid, polymer with formaldehyde, sodium salt, Cas No. 36290-04-7), 3 parts by weight of NK-D425 (2-naphthalenesulfonic acid, polymer with formaldehyde, sodium salt, Cas No. 36290-04-7), 1 part by weight of CR-SDS (sodium dodecyl sulfate, Cas No. 151-21-3), and 10 parts by weight of CR-UF100F (urea-formaldehyde resin (CAS no. 9011) -05-6)). Next, the remaining talc is mixed so that the total composition is 100 parts by weight, and then pulverized using an air jet mill. 10 to 12 parts by weight of water is added to the pulverized mixture, followed by kneading, granulating using a granulator, and then drying with hot air at about 80°C. Thus, a herbicidal composition having a water-dispersible granular formulation is prepared. Comparative Example 1 prepared a herbicidal composition having a suspension concentrate formulation in the same manner as in Example 1, but used a mixture of erythro-form and 12% by weight of its threo-form isomer including 88% by weight of FTS. Comparative Example 2 prepared a herbicidal composition with a suspension concentrate formulation in the same manner as in Example 1, but used a mixture of erythro-type and 15% by weight of its threo-type isomer including 85% by weight of FTS. Comparative Example 3 Prepared a herbicidal composition having a water-dispersible granular formulation in the same manner as in Example 3, but used a mixture of erythro-type and 12% by weight of its threo-type isomers including 88% by weight of FTS . [ Experimental example: Evaluation of storage stability of herbicidal composition ] To evaluate the storage stability of the herbicidal composition of Examples 1 to 3 and Comparative Examples 1 to 3, it was filled in a plastic bottle made of polyethylene (PE) Approximately 100 g of each liquid sample is packed in silver foil and filled with granular samples, and then sealed. Next, each encapsulated product was stored in an oven maintained at 54(±2)°C for 4 weeks, and then the area value of the active ingredient was measured using HPLC (manufactured by Waters) to evaluate the decomposition rate. The results are summarized in Table 1 below. The HPLC analysis conditions are as follows: Column: 100 mm×4.6 mm inner diameter "Capcell Pak" C18 column, 3 µm particle mobile phase: acetonitrile/water (0.02 M ammonium acetate + 0.1 M acetic acid) = 32/68 Flow rate: 1.0 mL/min. Column temperature: 30℃ Injection volume: 10 µl Detector wavelength: 254 nm Operation time: 20 minutes.
