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TWI713933B - Liquid herbicidal composition - Google Patents

Liquid herbicidal composition Download PDF

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Publication number
TWI713933B
TWI713933B TW107140593A TW107140593A TWI713933B TW I713933 B TWI713933 B TW I713933B TW 107140593 A TW107140593 A TW 107140593A TW 107140593 A TW107140593 A TW 107140593A TW I713933 B TWI713933 B TW I713933B
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Prior art keywords
pyridine
composition
herbicidal composition
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item
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TW107140593A
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Chinese (zh)
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TW201922097A (en
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柳基鉉
全三才
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南韓商Ｌｇ化學股份有限公司
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • A01N25/14—Powders or granules wettable
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/24—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients to enhance the sticking of the active ingredients

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The present invention relates to a liquid herbicidal composition, and more particularly, to a liquid herbicidal composition which includes an active ingredient and a buffer, wherein the active ingredient may comprise a pyridine sulfonylurea compound represented by Formula 1, and the buffer may have a pH of 5.80 to 6.25. The liquid herbicidal composition has excellent herbicidal activity, is improved in stability even when being prepared in liquid formulations, particularly, suspension concentrate formulations, and thus easily stored for a long time.

Description

液體除草組成物Liquid herbicidal composition

本發明關於液體除草組成物，且特別關於包括展現極佳的除草活性之除草活性成分的液體除草組成物。The present invention relates to a liquid herbicidal composition, and particularly to a liquid herbicidal composition including herbicidal active ingredients exhibiting excellent herbicidal activity.

在作物栽培技術中，重要的是藉由控制抑制作物生長之雜草以保護作物。為了降低由作物生長區域中產生的雜草所引起之損害，諸如降低作物生長或產率，已發展出能夠有效控制且對作物安全的除草活性材料。迄今已發展的許多除草活性材料經登記用於特定作物及用於控制雜草。較佳的是用於控制在生長此等作物之區域中產生的雜草之除草活性材料具有高的除草活性及寬廣的除草光譜，且對環境和作物是安全的。 同時，包括除草活性材料之除草組成物已發展成可濕性粉劑、可乳化濃縮物、水分散性粒劑、粒劑或懸浮濃縮物之調配物且用作為除草劑。然而，可濕性粉劑、可乳化濃縮物或水分散性粒劑調配物通常係藉由以水稀釋成預定濃度而製備成可噴霧液體，但是使其均勻地噴霧在稻田或田地的整個表面上卻有過高的成本及時間的問題，因為其應以大量施予。粒劑調配物可直接使用及因此可解決可濕性粉劑、可乳化濃縮物及水分散性粒劑調配物的問題。然而，粒劑調配物具有以除草劑總量為基礎計而相對低含量的除草活性材料、必需包括製備除草劑之輔助劑、具有複雜的製備方法，包括粉碎、混合、捏合、造粒、乾燥、分級等，且產生噴霧染污斑。為了克服該等調配物的問題，所以發展出具有相對簡單的製備方法、具有環保性且簡單及有效地噴霧之懸浮液濃縮調配物。同時，當除草組成物被用作為各種調配物中所製備之除草劑時，則重要的是確保除草組成物的穩定性，即使當長時間貯存時。 下式之化合物(提出之ISO名稱：氟吡磺隆(flucetosulfuron))為基於磺醯脲之除草活性材料且已先前於韓國專利第10-0399366號(韓國專利申請案第10-2000-0059990號)中說明為除草活性材料。 [式a]

Figure 02_image003
氟吡磺隆在土壤或葉面處理時對作物(諸如稻米、小麥、大麥)(適當的使用量：10至40克活性成分/公頃)及禾草(適當的使用量：50至200克活性成分/公頃)是安全的，且已知對各種類型之雜草展現極佳的除草效應，諸如闊葉型雜草、禾草雜草、莎草雜草、一年生雜草和多年生雜草。 然而，仍有確保包括此等基於磺醯脲之除草活性材料的除草組成物之穩定性的問題。特別難以長時間貯存懸浮液濃縮(SC)調配物，因為當在高溫下貯存時，穩定性係由於水解而進一步降低。 [先前文獻] [專利文獻] 韓國專利第10-0399366號In crop cultivation technology, it is important to protect crops by controlling weeds that inhibit crop growth. In order to reduce the damage caused by weeds produced in crop growing areas, such as reducing crop growth or yield, herbicidal active materials that can be effectively controlled and are safe to crops have been developed. Many herbicidal active materials that have been developed so far are registered for specific crops and for weed control. It is preferable that the herbicidal active material used to control weeds produced in areas where these crops are grown has high herbicidal activity and broad herbicidal spectrum, and is safe for the environment and crops. At the same time, herbicidal compositions including herbicidal active materials have been developed into formulations of wettable powders, emulsifiable concentrates, water-dispersible granules, granules or suspension concentrates and used as herbicides. However, wettable powders, emulsifiable concentrates, or water-dispersible granular formulations are usually prepared as sprayable liquids by diluting with water to a predetermined concentration, but making them spray evenly on the entire surface of the rice field or field But there is a problem of excessive cost and time, because it should be given in large amounts. Granule formulations can be used directly and therefore can solve the problems of wettable powders, emulsifiable concentrates and water-dispersible granular formulations. However, granular formulations have a relatively low content of herbicidal active materials based on the total amount of herbicides, must include auxiliary agents for the preparation of herbicides, and have complex preparation methods, including pulverization, mixing, kneading, granulation, and drying. , Classification, etc., and produce spray stains. In order to overcome the problems of these formulations, a relatively simple preparation method, environmentally friendly and simple and effective spraying suspension concentrate formulations have been developed. At the same time, when the herbicidal composition is used as the herbicide prepared in various formulations, it is important to ensure the stability of the herbicidal composition even when stored for a long time. The compound of the following formula (proposed ISO name: flucetosulfuron (flucetosulfuron)) is a herbicidal active material based on sulfonylurea and has been previously published in Korean Patent No. 10-0399366 (Korean Patent Application No. 10-2000-0059990) The description in) is a herbicidal active material. [Formula a]
Figure 02_image003
Flufenuron-methyl is effective on crops (such as rice, wheat, barley) (appropriate use amount: 10 to 40 g active ingredient/ha) and grasses (appropriate use amount: 50 to 200 g active Ingredients/hectare) is safe and is known to exhibit excellent herbicidal effects on various types of weeds, such as broadleaf weeds, grass weeds, sedge weeds, annual weeds, and perennial weeds. However, there is still a problem of ensuring the stability of herbicidal compositions including these herbicidal active materials based on sulfonylureas. It is particularly difficult to store suspension concentrate (SC) formulations for long periods of time because the stability is further reduced due to hydrolysis when stored at high temperatures. [Previous Document] [Patent Document] Korean Patent No. 10-0399366

[技術問題] 為了解決習知的問題，本發明旨在提供具有極佳的除草活性、具有高穩定性(即使當製備成液體調配物時)及易於高溫下經長時間貯存之液體除草組成物。 [技術手段] 本發明提供液體除草組成物，其包含： 活性成分，其包含以下列式1代表的吡啶磺醯脲化合物；及 具有5.80至6.25之pH的緩衝劑： [式1]

Figure 02_image005
在式1中， n為1至3的整數， R為氫或具有1至4個碳原子的烷基， R’為氫、具有1至4個碳原子的烷基、具有1至3個碳原子的鹵烷基、鹵基或具有1至2個碳原子的烷氧基，且 X和Y各自獨立為具有1至2個碳原子的烷基、具有1至2個碳原子的烷氧基、具有1至2個碳原子的鹵烷氧基或鹵基。 [有利效果] 根據本發明，可提供作為除草劑之液體除草組成物，其具有極佳的除草活性、低的分解率及極佳的穩定性(即使當製備成液體調配物、特別為懸浮液濃縮(SC)調配物時亦然)及易於高溫下經長時間貯存。 [本發明之模式] 本發明將於下文詳細說明。 在說明書及接續的申請專利範圍中所使用的術語或文字不應受限於常見或字典的含義，而應解釋為對應於本發明之具體實例的技術態樣之含義及觀念，其以本發明者可適當地定義術語而最適當地表達他/她的發明之原理為基礎。 根據本發明之例示性具體實例的液體除草組成物可包括活性成分及緩衝劑，其中活性成分可包含以下列式1代表的吡啶磺醯脲化合物，且緩衝劑可具有5.80至6.25之pH。 [式1]
Figure 02_image007
在式1中，n為1至3的整數，R為氫或具有1至4個碳原子的烷基，R’為氫、具有1至4個碳原子的烷基、具有1至3個碳原子的鹵烷基、鹵基或具有1至2個碳原子的烷氧基，且X和Y各自獨立為具有1至2個碳原子的烷基、具有1至2個碳原子的烷氧基、具有1至2個碳原子的鹵烷氧基或鹵基。 更佳地，在代表吡啶磺醯脲化合物的式1中，n為1或2的整數，R為氫或甲基，R’為氫、鹵基或甲基，且X和Y各自獨立為甲氧基，且甚至更佳地，n為1或2的整數，R為甲基，R’為氫、氯(Cl)、溴(Br)或甲基，且X和Y各自獨立為甲氧基。 根據本發明之例示性具體實例的式1之吡啶磺醯脲化合物可為一或多種選自下列之化合物：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，以式1代表的吡啶磺醯脲化合物可為下列式2之化合物(提出之ISO名稱：氟吡磺隆)。 [式2]
Figure 02_image009
在根據本發明之例示性具體實例的液體除草組成物中，活性成分的內含量可以相對於100重量份的液體除草組成物而為1至50重量份，較佳為1至25重量份，且更佳為3至15重量份。當液體除草組成物包括少於1重量份的活性成分時，則由於除草組成物中的活性成分含量非常少，即使僅分解少量的活性成分，但相對的分解率(%)快速增加，導致降低的除草效應，且當包括超過50重量份的活性成分時，則可能引起產物具有降低的物理及/或化學特性的問題，例如增加的黏度。 同時，在液體調配物的例子中，由於包括以式1代表的吡啶磺醯脲化合物之活性成分的水解而有穩定性降低的問題。然而，根據本發明之例示性具體實例的液體除草組成物係藉由適當地控制緩衝液之pH以顯著地降低分解率而確保穩定性，即使以液體調配物。 根據本發明之例示性具體實例的液體除草組成物可具有5.80至6.25之pH，較佳為6.00至6.20之pH，且更佳為6.10至6.20之pH，且pH可以緩衝劑控制。亦即，本發明之液體除草組成物可包括具有5.80至6.25，較佳為6.00至6.20，且更佳為6.10至6.20之pH的緩衝劑。在本發明中，液體除草組成物之pH可由於液體除草組成物的水解而為影響分解率的因素之一，且若pH係在5.80至6.25之範圍內，即時以長期高溫貯存液體除草組成物，分解率仍為低的，且因此明顯地改進穩定性。 緩衝劑較佳為基於磷酸鹽之緩衝劑、碳酸與碳酸氫鈉之混合溶液(H2 CO3 /NaHCO3 之混合溶液)或Bis-Tris溶液，且尤其包括磷酸氫二鉀(K2 HPO4 )、磷酸二氫鉀(KH2 PO4 )、磷酸氫二鈉(Na2 HPO4 )、磷酸二氫鈉(NaH2 PO4 )、碳酸與碳酸氫鈉之混合溶液(H2 CO3 /NaHCO3 之混合溶液)及Bis-Tris溶液中之一或多者，且更尤其包括磷酸氫二鉀、磷酸二氫鉀、磷酸氫二鈉、磷酸二氫鈉或其混合物。 另外，當緩衝劑為混合溶液時，則可控制緩衝劑之混合比，使得整體緩衝劑具有5.80至6.25之pH。 本文所使用之術語「Bis-Tris溶液」為含有Bis-Tris之溶液，該Bis-Tris為那些一般熟習此項技術領域者熟知的化合物，且IUPAC名稱為2-[雙(2-羥乙基)胺基]-2-(羥甲基)丙-1,3-二醇及CAS編號為6976-37-0。 而且，緩衝劑可為具有0.03至0.2M，較佳為0.05至0.1M之濃度的溶液。當緩衝劑滿足上述的數字範圍時，則進一步降低液體除草組成物的分解率及改進穩定性。另外，如本發明，當濃度為0.2M或更低時，則由於極佳的黏度而易於製備除草組成物。 根據本發明之例示性具體實例的液體除草組成物可進一步包括界面活性劑，其促進活性成分的可濕性及分散性且有助於維持組成物經長時間的懸浮穩定性。 另外，界面活性劑的內含量可以相對於100重量份的液體除草組成物而為1至20重量份，尤其為1至10重量份。 界面活性劑的類型可為陰離子界面活性劑及非離子界面活性劑(特別為非離子界面活性劑)中的聚合性界面活性劑。特定言之，陰離子界面活性劑可為基於磺基琥珀酸二辛酯鈉鹽、基於磺基琥珀酸二辛酯鈣鹽或基於α-烯烴磺酸鹽之界面活性劑，及非離子界面活性劑可為以包括環氧乙烷單元之環氧乙烷接枝共聚物、氧乙烯與氧丙烯之共聚物、聚氧乙烯三苯乙烯基苯醚、基於羧酸酯之聚合物或蔗糖月桂酸酯為基礎之界面活性劑。 根據本發明之例示性具體實例的液體除草組成物可進一步包括防凍劑，其內含量可以相對於100重量份的總液體除草組成物而為0.01至10重量份，尤其為1.0至6.0重量份，且更尤其為2.0至4.0重量份，且甚至更尤其為2.0至3.0重量份，因為其具有防凍效應及大大地改進分解率。 另外，防凍劑可包括基於二醇之化合物及基於醇之化合物，且基於二醇之化合物尤其可包括丙二醇(P.G.)、乙二醇、二乙二醇、二丙二醇及三丙二醇，及基於醇之化合物可包括甘油及異丙醇，且較佳為丙二醇。 在本發明中，當上述類型之防凍劑的內含量係在上述的數字範圍內時，則其具有極佳的防凍效應及降低液體除草組成物的分解率之效應。另外，當防凍劑的含量比超過上述的數字範圍時，則可增加液體除草組成物的分解率且因此可降低穩定性。當防凍劑的內含量少於上述的數字範圍時，則其含量無意義且不可能實現充分的防凍效應。 根據本發明之例示性具體實例的液體除草組成物可包括增稠劑，且增稠劑的內含量較佳地以相對於100重量份的總液體除草組成物而為0.001至1.2重量份或更少，尤其為0.05至1.0重量份，且更尤其為0.05至0.15重量份。 另外，增稠劑可為通常可用於相關技術中的任何增稠劑而沒有限制，且尤其可包括三仙膠、皂土、矽礬石黏土、微晶高嶺石、阿拉伯膠、瓜爾膠、基於纖維素之化合物、藻酸鈉、澱粉或其混合物，且較佳為三仙膠、微晶高嶺石或其混合物。 根據本發明之例示性具體實例，當增稠劑的內含量係在上述的數字範圍內時，則改進增稠效應且降低液體除草組成物的分解率。 根據本發明之例示性具體實例，在液體除草組成物中，除了上述組份以外，若必要時可進一步包括消泡劑、保存劑、穩定劑、顏料等。 而且，根據本發明之例示性具體實例，液體除草組成物可由緩衝劑所組成，該緩衝劑為除了作為活性成分之以式1代表的化合物、界面活性劑、防凍劑、增稠劑及添加劑(諸如消泡劑、保存劑、穩定劑等)的含量以外的剩餘物。換言之，緩衝劑的含量可為除了相對於100重量%之液體除草組成物的其他組份含量以外的量。 另外，根據本發明之例示性具體實例，可使用任何液體調配物作為液體除草組成物之調配物而沒有限制，且尤其為液體溶液或懸浮液濃縮(SC)調配物，且更尤其為懸浮液濃縮調配物。懸浮液濃縮調配物在此可為水分散型懸浮液調配物。 當包括上述活性成分之除草組成物製備成懸浮液濃縮調配物時，則由於水解的高分解率而難以長期貯存除草組成物。因此，在本發明中，具有改進之穩定性及易於經長時間貯存之液體除草組成物可藉由控制液體除草組成物之pH來製備。 根據本發明之例示性具體實例的液體除草組成物包括控制pH之緩衝劑，儘管組成物為液體，但是由於液體除草組成物的受控制之pH範圍，使得吡啶磺醯脲化合物之磺醯脲基團免於水解而顯著地降低由於水解的分解率，由此確保液體調配物的穩定性及促進長期貯存。因此，本發明可解決具有液體調配物之習知的除草組成物之低穩定性的問題，該組成物含有因大部分的活性成分水解所造成的少量活性成分，因為組成物係由於水解而具有非常高的分解率。[Technical Problem] In order to solve the conventional problems, the present invention aims to provide a liquid herbicidal composition with excellent herbicidal activity, high stability (even when prepared as a liquid formulation) and easy to store for a long time at high temperature . [Technical Means] The present invention provides a liquid herbicidal composition comprising: an active ingredient comprising a pyridine sulfonylurea compound represented by the following formula 1; and a buffer having a pH of 5.80 to 6.25: [Formula 1]
Figure 02_image005
In Formula 1, n is an integer from 1 to 3, R is hydrogen or an alkyl group having 1 to 4 carbon atoms, and R'is hydrogen, an alkyl group having 1 to 4 carbon atoms, having 1 to 3 carbons A haloalkyl group, a halo group or an alkoxy group having 1 to 2 carbon atoms, and X and Y are each independently an alkyl group having 1 to 2 carbon atoms or an alkoxy group having 1 to 2 carbon atoms , Haloalkoxy or halo having 1 to 2 carbon atoms. [Advantageous effect] According to the present invention, a liquid herbicidal composition as a herbicide can be provided, which has excellent herbicidal activity, low decomposition rate and excellent stability (even when prepared as a liquid formulation, especially a suspension Concentrated (SC) formulations) and easy to store for a long time at high temperature. [Modes of the present invention] The present invention will be described in detail below. The terms or words used in the specification and subsequent patent applications should not be limited to common or dictionary meanings, but should be interpreted as meanings and concepts corresponding to the technical aspects of the specific examples of the present invention. The person can define the terms appropriately and best express the principle of his/her invention. The liquid herbicidal composition according to the exemplary embodiment of the present invention may include an active ingredient and a buffer, wherein the active ingredient may include a pyridine sulfonylurea compound represented by the following formula 1, and the buffer may have a pH of 5.80 to 6.25. [Formula 1]
Figure 02_image007
In Formula 1, n is an integer from 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, and having 1 to 3 carbon atoms. A haloalkyl group, a halo group or an alkoxy group having 1 to 2 carbon atoms, and X and Y are each independently an alkyl group having 1 to 2 carbon atoms or an alkoxy group having 1 to 2 carbon atoms , Haloalkoxy or halo having 1 to 2 carbon atoms. More preferably, in Formula 1 representing the pyridine sulfonylurea compound, n is an integer of 1 or 2, R is hydrogen or methyl, R'is hydrogen, halo or methyl, and X and Y are each independently methyl Oxy, and even more preferably, n is an integer of 1 or 2, R is methyl, R'is hydrogen, chlorine (Cl), bromine (Br) or methyl, and X and Y are each independently methoxy . The pyridine sulfonylurea compound of Formula 1 according to an exemplary embodiment of the present invention may be one or more compounds selected from: N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl] -2-(2-Fluoro-1-methoxyacetoxy-n-propyl)pyridine-3-sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)amino Carbonyl]-2-(2-fluoro-1-hydroxyacetoxy-n-propyl)pyridine-3-sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)amino Carbonyl]-2-(2-fluoro-1-(3-hydroxypropionyl)oxy-n-propyl)pyridine-3-sulfonamide, N-[(4,6-dimethoxypyrimidine-2- Yl)aminocarbonyl)-2-(2-fluoro-1-(3-methoxypropionyl)oxy-n-propyl)pyridine-3-sulfonamide, N-((4,6-dimethyl Oxypyrimidin-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-sulfon Amide 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 a compound of the following Formula 2 (proposed ISO name: flufenuron-methyl). [Equation 2]
Figure 02_image009
In the liquid herbicidal composition according to the exemplary embodiment of the present invention, the internal content of the active ingredient may be 1 to 50 parts by weight, preferably 1 to 25 parts by weight, relative to 100 parts by weight of the liquid herbicidal composition, and More preferably, it is 3 to 15 parts by weight. When the liquid herbicidal composition includes less than 1 part by weight of the active ingredient, since the active ingredient content in the herbicidal composition is very small, even if only a small amount of active ingredient is decomposed, the relative decomposition rate (%) increases rapidly, resulting in a decrease When it includes more than 50 parts by weight of active ingredients, it may cause problems with reduced physical and/or chemical properties of the product, such as increased viscosity. Meanwhile, in the example of the liquid formulation, there is a problem of decreased stability due to the hydrolysis of the active ingredient including the pyridine sulfonylurea compound represented by Formula 1. However, the liquid herbicidal composition system according to the exemplary embodiment of the present invention ensures stability by appropriately controlling the pH of the buffer solution to significantly reduce the decomposition rate, even with a liquid formulation. The liquid herbicidal composition according to the exemplary embodiment of the present invention may have a pH of 5.80 to 6.25, preferably a pH of 6.00 to 6.20, and more preferably a pH of 6.10 to 6.20, and the pH can be controlled by a buffer. That is, the liquid herbicidal composition of the present invention may include a buffer having a pH of 5.80 to 6.25, preferably 6.00 to 6.20, and more preferably 6.10 to 6.20. In the present invention, the pH of the liquid herbicidal composition can be one of the factors affecting the decomposition rate due to the hydrolysis of the liquid herbicidal composition, and if the pH is in the range of 5.80 to 6.25, the liquid herbicidal composition can be stored immediately at a long-term high temperature , The decomposition rate is still low, and therefore the stability is significantly improved. The buffer is preferably a phosphate-based buffer, a mixed solution of carbonic acid and sodium bicarbonate (a mixed solution of H 2 CO 3 /NaHCO 3 ) or a Bis-Tris solution, and especially includes 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 mixed solution of carbonic acid and sodium bicarbonate (H 2 CO 3 /NaHCO 3 ) and one or more of the Bis-Tris solution, and more particularly include dipotassium hydrogen phosphate, potassium dihydrogen phosphate, disodium hydrogen phosphate, sodium dihydrogen phosphate, or mixtures thereof. In addition, when the buffer is a mixed solution, the mixing ratio of the buffer can be controlled so that the overall buffer has a pH of 5.80 to 6.25. As used herein, the term "Bis-Tris solution" refers to a solution containing Bis-Tris. The 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 and its CAS number is 6976-37-0. Moreover, the buffer may be a solution having a concentration of 0.03 to 0.2M, preferably 0.05 to 0.1M. When the buffer meets the above numerical range, the decomposition rate of the liquid herbicidal composition is further reduced and the stability is improved. In addition, as in the present invention, when the concentration is 0.2 M or less, it is easy to prepare the herbicidal composition due to the excellent viscosity. The liquid herbicidal composition according to the exemplary embodiment of the present invention may further include a surfactant, which promotes the wettability and dispersibility of the active ingredient and helps maintain the suspension stability of the composition over a long period of time. In addition, the internal content of the surfactant may be 1 to 20 parts by weight, especially 1 to 10 parts by weight, relative to 100 parts by weight of the liquid herbicidal composition. The type of surfactant may be a polymeric surfactant among anionic surfactants and nonionic surfactants (especially nonionic surfactants). In particular, the anionic surfactant can be a surfactant based on dioctyl sulfosuccinate sodium salt, dioctyl sulfosuccinate calcium salt or α-olefin sulfonate-based surfactants, and nonionic surfactants It can be an ethylene oxide graft copolymer including ethylene oxide units, a copolymer of oxyethylene and oxypropylene, polyoxyethylene tristyryl phenyl ether, a polymer based on carboxylate, or sucrose laurate It is the basic surfactant. The liquid herbicidal composition according to the exemplary embodiment of the present invention may further include an antifreeze, and the content thereof may be 0.01 to 10 parts by weight, especially 1.0 to 6.0 parts by weight, relative to 100 parts by weight of the total liquid herbicidal composition, And more particularly 2.0 to 4.0 parts by weight, and even more particularly 2.0 to 3.0 parts by weight, because it has an antifreeze effect and greatly improves the decomposition rate. In addition, the antifreeze agent may include glycol-based compounds and alcohol-based compounds, and glycol-based compounds may especially include propylene glycol (PG), ethylene glycol, diethylene glycol, dipropylene glycol, and tripropylene glycol, and alcohol-based compounds. The compound may include glycerin and isopropanol, and is preferably propylene glycol. In the present invention, when the internal content of the above-mentioned type of antifreeze agent is within the above-mentioned numerical range, it has an excellent antifreeze effect and an effect of reducing the decomposition rate of the liquid herbicidal composition. In addition, when the content ratio of the antifreeze agent exceeds the above-mentioned numerical range, the decomposition rate of the liquid herbicidal composition may be increased and thus the stability may be reduced. When the internal content of the antifreeze agent is less than the above-mentioned numerical range, its content is meaningless and it is impossible to achieve a sufficient antifreeze effect. The liquid herbicidal composition according to the exemplary embodiment of the present invention may include a thickener, and the internal content of the thickener is preferably 0.001 to 1.2 parts by weight or more relative to 100 parts by weight of the total liquid herbicidal composition Less, especially 0.05 to 1.0 part by weight, and more especially 0.05 to 0.15 part by weight. In addition, the thickening agent may be any thickening agent generally used in related technologies without limitation, and in particular may include sanxian gum, bentonite, alumite clay, microcrystalline kaolinite, gum arabic, guar gum, Cellulose-based compounds, sodium alginate, starch or mixtures thereof, and preferably trixian gum, microcrystalline kaolinite or mixtures thereof. According to an exemplary embodiment of the present invention, when the internal content of the thickener is within the above-mentioned numerical range, the thickening effect is improved and the decomposition rate of the liquid herbicidal composition is reduced. According to an exemplary embodiment of the present invention, in the liquid herbicidal composition, in addition to the above-mentioned components, if necessary, it may further include defoamers, preservatives, stabilizers, pigments, etc. Furthermore, according to the exemplary embodiment of the present invention, the liquid herbicidal composition may be composed of a buffering agent, which is a compound represented by Formula 1 as an active ingredient, a surfactant, an antifreeze agent, a thickener, and an additive ( (Such as defoamers, preservatives, stabilizers, etc.) other than the content. In other words, the content of the buffering agent may be an amount other than the content of other components relative to 100% by weight of the liquid herbicidal composition. In addition, according to the illustrative examples of the present invention, any liquid formulation can be used as the formulation of the liquid herbicidal composition without limitation, and is especially a liquid solution or a suspension concentrate (SC) formulation, and more particularly a suspension Concentrate the formulation. The suspension concentrate formulation can be a water-dispersible suspension formulation. When the herbicidal composition including the above-mentioned active ingredients is prepared as a suspension concentrate formulation, it is difficult to store the herbicidal composition for a long time due to the high decomposition rate of hydrolysis. Therefore, in the present invention, a liquid herbicidal composition with improved stability and easy storage for a long time can be prepared by controlling the pH of the liquid herbicidal composition. The liquid herbicidal composition according to the exemplary embodiment of the present invention includes a pH-controlling buffer. Although the composition is liquid, due to the controlled pH range of the liquid herbicidal composition, the sulfonylurea group of the pyridine sulfonylurea compound The mass is prevented from hydrolysis and significantly reduces the decomposition rate due to hydrolysis, thereby ensuring the stability of the liquid formulation and promoting long-term storage. Therefore, the present invention can solve the problem of low stability of the conventional herbicidal composition with liquid formulations, the composition containing a small amount of active ingredients caused by the hydrolysis of most of the active ingredients, because the composition has Very high decomposition rate.

實施例 在下文，為幫助理解本發明，提出例示性實施例。然而，應理解實施例的提供並非限制本發明之範圍，且在所附申請專利範圍內的所有替代物及修飾皆包括在本發明中。 實施例1 製備方法大致分成兩個程序，諸如濕部分程序及增稠部分程序，且在室溫下進行。 製備0.1M 磷酸鹽緩衝劑(pH 6.15)：將水添加至K2 HPO4 及KH2 PO4 中以製備1公升溶液。然後將3.0重量份的CR-DOS70P磺基琥珀酸(二(2-乙基己基)酯鈉鹽，Cas編號577-11-7)、1.0重量份的NK-SU500 (蔗糖月桂酸酯，Cas編號25339-99-5)及作為消泡劑之0.2重量份的SAG-622 (Momentive)添加至65.8重量份的緩衝劑中且充分混合。在均化狀態下，將10.0重量份的乙酸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-氟丙基甲氧酯(氟吡磺隆，FTS)添加至混合物中，隨後使用攪拌器充分混合。在此使用玻璃珠研磨混合物，直到平均粒徑成為1至2微米為止，由此獲得濕部分。 然後將0.1重量份的X.G (三仙膠，Cas編號11138-66-2)0.2重量份的M.V [5-氯-2-甲基-4-異噻唑啉-3-酮(Cas編號26172-55-4)及2-甲基-4-異噻唑啉-3-酮(Cas編號2682-20-4)]添加至3.0重量份的P.G (丙二醇，Cas編號57-55-6)中且充分攪拌。接著將16.7重量份的0.1M磷酸鹽緩衝劑(pH 6.15)(其中將K2 HPO4 與KH2 PO4 在水中混合)添加至其中，隨後充分攪拌。 將20重量份的增稠部分添加至80重量份的濕部分中且充分攪拌，得到具有懸浮液濃縮調配物之除草組成物。 實施例2 具有懸浮液濃縮調配物之除草組成物係以與實施例1相同的方式製備，除了濕部分緩衝劑及增稠部分緩衝劑之pH改變成5.8以外。 實施例3 具有懸浮液濃縮調配物之除草組成物係以與實施例1相同的方式製備，除了添加2重量份的丙二醇及對增稠部分添加17.7重量份的磷酸鹽緩衝劑以外。 實施例4 具有懸浮液濃縮調配物之除草組成物係以與實施例1相同的方式製備，除了添加4重量份的丙二醇對增稠部分添加15.7重量份的磷酸鹽緩衝劑以外。 比較例1 具有懸浮液濃縮調配物之除草組成物係以與實施例1相同的方式製備，除了濕部分緩衝劑及增稠部分緩衝劑之pH改變成5.5以外。 比較例2 具有懸浮液濃縮調配物之除草組成物係以與實施例1相同的方式製備，除了濕部分緩衝劑及增稠部分緩衝劑之pH改變成6.3以外。 比較例3 具有懸浮液濃縮調配物之除草組成物係以與實施例1相同的方式製備，除了濕部分緩衝劑及增稠部分緩衝劑之pH改變成6.8以外。 比較例4 具有懸浮液濃縮調配物之除草組成物係以與實施例1相同的方式製備，除了濕部分緩衝劑及增稠部分緩衝劑之pH改變成7.4以外。 實驗例：評估液體除草組成物之貯存穩定性 為了評估實施例及比較例的液體除草組成物之貯存穩定性，將約100毫升各樣品填充至聚乙烯瓶中且接著密封，隨後貯存在維持於54(±2)℃之烘箱中4週。接著以HPLC (由Waters製造)測量活性成分之面積值以評估分解率，且將結果顯示於以下表1中。 HPLC分析條件係如下： 管柱：100毫米 X 4.6毫米內徑「Capcell Pak」C18管柱，3微米粒子 移動相：乙腈/水(0.02M乙酸銨 + 0.1M乙酸) = 32/68 流速：1.0毫升/分鐘 管柱溫度：30℃ 注入體積：10微升 檢測波長：254奈米 操作時間：20分鐘 [表1]

Figure 107140593-A0304-0001
如表1中所示，可確認在實施例1至4中的根據本發明之例示性具體實例的液體除草組成物(其包括作為活性成分的吡啶磺醯脲化合物及具有5.80至6.25之pH的緩衝劑)具有比其中緩衝劑之pH範圍超出本發明之範圍的比較例1至4中的那些液體除草組成物更低的分解率，且因此彼等具有高的穩定性，即使在高溫經長時間的貯存期間亦然。 當實施例中的緩衝劑溶液之pH相同時，亦可觀察出含有2.0至3.0重量份的防凍劑之實施例1和3的分解率甚至更低。 雖然本發明已參考具體的細節(諸如特定的組份等)及有限的實施例和圖形予以說明，但是彼等的提供僅為了有助於全面理解本發明。然而，不應該理解為本發明不受限於該等實施例，且因此那些一般熟習此項技術領域者可自上述說明進行各種修飾及變更。 因此，本發明之範圍不應受限於上文所述之實施例，且意欲使所有的修飾及等效物以及後列的申請專利範圍皆在本發明之範圍內。Examples Hereinafter, to help understand the present invention, illustrative examples are presented. However, it should be understood that the provision of the embodiments does not 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. Example 1 The preparation method is roughly divided into two procedures, such as a wet part procedure and a thickening part procedure, and they are carried out at room temperature. Preparation of 0.1M phosphate buffer (pH 6.15): water was added to K 2 HPO 4 and KH 2 PO 4 to prepare 1 liter of solution. Then 3.0 parts by weight of CR-DOS70P (bis(2-ethylhexyl) sulfosuccinate sodium salt, Cas number 577-11-7), 1.0 parts by weight of NK-SU500 (sucrose laurate, Cas number 25339-99-5) and 0.2 parts by weight of SAG-622 (Momentive) as a defoamer were added to 65.8 parts by weight of buffer and mixed thoroughly. In the homogenized state, 10.0 parts by weight of acetic acid 1-(3-{[(4,6-dimethoxy-pyrimidin-2-yl)aminomethanyl]sulfonamide}-2-pyridyl )-2-Fluoropropyl methoxyester (flupisulfuron, FTS) was added to the mixture, and then mixed thoroughly using a stirrer. Here, glass beads are used to grind the mixture until the average particle size becomes 1 to 2 microns, thereby obtaining a wet portion. Then 0.1 parts by weight of XG (Sanxian gum, Cas number 11138-66-2) and 0.2 parts by weight of MV [5-chloro-2-methyl-4-isothiazolin-3-one (Cas number 26172-55) -4) and 2-methyl-4-isothiazolin-3-one (Cas number 2682-20-4)] were added to 3.0 parts by weight of PG (propylene glycol, Cas number 57-55-6) and fully stirred . Next, 16.7 parts by weight of 0.1M phosphate buffer (pH 6.15) (in which K 2 HPO 4 and KH 2 PO 4 are mixed in water) was added thereto, followed by thorough stirring. 20 parts by weight of the thickening part was added to 80 parts by weight of the wet part and fully stirred to obtain a herbicidal composition having a concentrated suspension formulation. Example 2 The herbicidal composition with the suspension concentrate formulation was prepared in the same manner as in Example 1, except that the pH of the wet part buffer and the thickening part buffer was changed to 5.8. Example 3 A herbicidal composition with a suspension concentrate formulation 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 was added to the thickened part. Example 4 A herbicidal composition with a suspension concentrate formulation was prepared in the same manner as in Example 1, except that 4 parts by weight of propylene glycol was added to the thickened part and 15.7 parts by weight of phosphate buffer was added. Comparative Example 1 A herbicidal composition with a suspension concentrate formulation was prepared in the same manner as in Example 1, except that the pH of the wet part buffer and the thickening part buffer was changed to 5.5. Comparative Example 2 A herbicidal composition with a suspension concentrate formulation was prepared in the same manner as in Example 1, except that the pH of the wet part buffer and the thickening part buffer was changed to 6.3. Comparative Example 3 A herbicidal composition with a suspension concentrate formulation was prepared in the same manner as in Example 1, except that the pH of the wet part buffer and the thickening part buffer was changed to 6.8. Comparative Example 4 A herbicidal composition with a suspension concentrate formulation was prepared in the same manner as in Example 1, except that the pH of the wet part buffer and the thickening part buffer was changed to 7.4. Experimental example: Evaluation of the storage stability of the liquid herbicidal composition In order to evaluate the storage stability of the liquid herbicidal composition of the Examples and Comparative Examples, approximately 100 ml of each sample was filled into a polyethylene bottle and then sealed, and then stored in 54(±2)℃ in an oven for 4 weeks. The area value of the active ingredient was then measured by HPLC (manufactured by Waters) to evaluate the decomposition rate, and the results are shown in Table 1 below. The HPLC analysis conditions are as follows: Column: 100 mm X 4.6 mm inner diameter "Capcell Pak" C18 column, 3 micron particles Mobile phase: acetonitrile/water (0.02M ammonium acetate + 0.1M acetic acid) = 32/68 Flow rate: 1.0 Ml/min Column temperature: 30℃ Injection volume: 10 microliters Detection wavelength: 254 nm Operation time: 20 minutes [Table 1]
Figure 107140593-A0304-0001
 As shown in Table 1, it can be confirmed that the liquid herbicidal composition according to the illustrative specific examples of the present invention in Examples 1 to 4 (which includes a pyridine sulfonylurea compound as an active ingredient and a pH of 5.80 to 6.25) Buffer) has a lower decomposition rate than those liquid herbicidal compositions in Comparative Examples 1 to 4 in which the pH range of the buffer is outside the scope of the present invention, and therefore they have high stability even at high temperatures The same applies to the storage period of time. When the pH of the buffer solution in the examples is the same, it can also be observed that the decomposition rate of Examples 1 and 3 containing 2.0 to 3.0 parts by weight of antifreeze is even lower. Although the present invention has been described with reference to specific details (such as specific components, etc.) and limited embodiments and figures, they are only provided to facilitate a comprehensive understanding of the present invention. However, it should not be understood that the present invention is not limited to these embodiments, and therefore those who are generally familiar with the technical field can make various modifications and changes from the above description. Therefore, the scope of the present invention should not be limited to the above-mentioned embodiments, and it is intended that all modifications and equivalents and the scope of the following patent applications are within the scope of the present invention.

Figure 107140593-A0101-11-0002-1
Figure 107140593-A0101-11-0002-1

Claims (10)

一種液體除草組成物，其包含：活性成分，其包含以下列式1代表的吡啶磺醯脲化合物；及具有5.80至6.25之pH的緩衝劑：
Figure 107140593-A0305-02-0019-2
 在式1中，n為1至3的整數，R為氫或具有1至4個碳原子的烷基，R’為氫、具有1至4個碳原子的烷基、具有1至3個碳原子的鹵烷基、鹵基或具有1至2個碳原子的烷氧基，且X和Y各自獨立為具有1至2個碳原子的烷基、具有1至2個碳原子的烷氧基、具有1至2個碳原子的鹵烷氧基或鹵基，其中該緩衝劑包括一或多種選自由下列所組成之群組：磷酸氫二鉀(K2HPO4)、磷酸二氫鉀(KH2PO4)、磷酸氫二鈉(Na2HPO4)及磷酸二氫鈉(NaH2PO4)， 其中該活性成分的內含量係以相對於100重量份的該液體除草組成物而為1至50重量份，以及其中該液體除草組成物經製備成懸浮液濃縮(SC)調配物。 A liquid herbicidal composition comprising: an active ingredient comprising a pyridine sulfonylurea compound represented by the following formula 1; and a buffer having a pH of 5.80 to 6.25:
Figure 107140593-A0305-02-0019-2
 In Formula 1, n is an integer from 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, and having 1 to 3 carbon atoms. A haloalkyl group, a halo group or an alkoxy group having 1 to 2 carbon atoms, and X and Y are each independently an alkyl group having 1 to 2 carbon atoms or an alkoxy group having 1 to 2 carbon atoms , A haloalkoxy or halo group having 1 to 2 carbon atoms, wherein the buffer includes one or more 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 ), wherein the content of the active ingredient is relative to 100 parts by weight of the liquid herbicidal composition 1 to 50 parts by weight, and wherein the liquid herbicidal composition is prepared into a suspension concentrate (SC) formulation. 根據申請專利範圍第1項之組成物，其中，該緩衝劑之pH為6.0至6.2。 The composition according to item 1 of the scope of patent application, wherein the pH of the buffer is 6.0 to 6.2. 根據申請專利範圍第1項之組成物，其中，該緩衝劑進一步包括一或多種選自由下列所組成之群組：碳酸與碳酸氫鈉之混合溶液(H2CO3/NaHCO3之混合溶液)及Bis-Tris溶液。 According to the composition of item 1 of the scope of patent application, the buffering agent further includes one or more selected from the group consisting of: a mixed solution of carbonic acid and sodium bicarbonate (a mixed solution of H 2 CO 3 /NaHCO 3 ) And Bis-Tris solution. 根據申請專利範圍第1項之組成物，其中，該緩衝劑濃度為0.03M至0.2M。 According to the composition of item 1 of the scope of patent application, the buffer concentration is 0.03M to 0.2M. 根據申請專利範圍第1項之組成物，其中，在式1中，n為1或2的整數，R為氫或甲基，R’為氫、鹵基或甲基，且X和Y各自獨立為甲氧基。 The composition according to item 1 of the scope of patent application, wherein in formula 1, n is an integer of 1 or 2, R is hydrogen or methyl, R'is hydrogen, halo or methyl, and X and Y are each independent It is methoxy. 根據申請專利範圍第1項之組成物，其中，以式1代表的該吡啶磺醯脲化合物包括一或多種選自由下列所組成之群組：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。 According to the composition of item 1 of the scope of patent application, the pyridine sulfonylurea compound represented by formula 1 includes one or more selected from the group consisting of: N-[(4,6-dimethoxypyrimidine -2-yl)aminocarbonyl)-2-(2-fluoro-1-methoxyacetoxy-n-propyl)pyridine-3-sulfonamide, N-((4,6-dimethoxy base Pyrimidine-2-yl)aminocarbonyl)-2-(2-fluoro-1-hydroxyacetoxy-n-propyl)pyridine-3-sulfonamide, N-[(4,6-dimethoxy Pyrimidine-2-yl)aminocarbonyl]2-(2-fluoro-1-(3-hydroxypropionyl)oxy-n-propyl)pyridine-3-sulfonamide, N-[(4,6-di Methoxypyrimidin-2-yl)aminocarbonyl]-2-(2-fluoro-1-(3-methoxypropionyl)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 Yl)pyridine-3-sulfonamide and N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-4-bromo-2-(2-fluoro-1-methoxyethyl (Oxy-n-propyl)pyridine-3-sulfonamide. 根據申請專利範圍第1項之組成物，其中，以式1代表的該吡啶磺醯脲化合物為以下列式2代表的化合物：
Figure 107140593-A0305-02-0021-3
 According to the composition of item 1 of the scope of patent application, the pyridine sulfonylurea compound represented by formula 1 is a compound represented by the following formula 2:
Figure 107140593-A0305-02-0021-3
 根據申請專利範圍第1項之組成物，其中，該液體除草組成物進一步包括防凍劑，其包括一或多種選自由下列所組成之群組：基於二醇之化合物及基於醇之化合物。 The composition according to item 1 of the scope of patent application, wherein the liquid herbicidal composition further includes an antifreeze, which includes one or more selected from the group consisting of diol-based compounds and alcohol-based compounds. 根據申請專利範圍第8項之組成物，其中，該防凍劑包括一或多種選自由下列所組成之群組：丙二醇、乙二醇、二乙二醇、二丙二醇、三丙二醇、甘油及異丙醇。 According to the composition of item 8 of the scope of patent application, the antifreeze agent includes one or more selected from the group consisting of propylene glycol, ethylene glycol, diethylene glycol, dipropylene glycol, tripropylene glycol, glycerin and isopropyl alcohol. 根據申請專利範圍第8項之組成物，其中，該防凍劑的內含量係以相對於100重量份的該液體除草組成物而為0.01至10.0重量份。 According to the composition of item 8 of the scope of patent application, the internal content of the antifreeze is 0.01 to 10.0 parts by weight relative to 100 parts by weight of the liquid herbicidal composition.
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