JP3253392B2 - Improved herbicidal composition - Google Patents

Improved herbicidal composition

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Publication number
JP3253392B2
JP3253392B2 JP36199592A JP36199592A JP3253392B2 JP 3253392 B2 JP3253392 B2 JP 3253392B2 JP 36199592 A JP36199592 A JP 36199592A JP 36199592 A JP36199592 A JP 36199592A JP 3253392 B2 JP3253392 B2 JP 3253392B2
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JP
Japan
Prior art keywords
weight
parts
compound
salt
formulation example
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
JP36199592A
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Japanese (ja)
Other versions
JPH05271021A (en
Inventor
博 吉井
勝 前田
弘司 菊川
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ishihara Sangyo Kaisha Ltd
Original Assignee
Ishihara Sangyo Kaisha Ltd
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Priority to JP36199592A priority Critical patent/JP3253392B2/en
Publication of JPH05271021A publication Critical patent/JPH05271021A/en
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Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【0001】[0001]

【産業上の利用分野】本発明は、1−(4,6−ジメト
キシピリミジン−2−イル)−3−(3−トリフルオロ
メチル−2−ピリジルスルホニル)ウレア(以下化合物
Aと略す)又はその塩とホモアラニン−4−イル(メチ
ル)ホスフィン酸(以下化合物Bと略す)、2−アミノ
−4−〔(ヒドロキシ)(メチル)ホスフィノイル〕ブ
チリルアラニルアラニン(以下化合物Cと略す)、N−
(ホスホノメチル)グリシン(以下化合物Dと略す)及
びそれらの塩から成る群より選ばれた少なくとも1種と
を有効成分として含有する除草組成物に、無機マグネシ
ウム塩を添加することを特徴とする、改良された除草組
成物に関する。
The present invention relates to 1- (4,6-dimethoxypyrimidin-2-yl) -3- (3-trifluoromethyl-2-pyridylsulfonyl) urea (hereinafter abbreviated as compound A) or a compound thereof. Salt and homoalanin-4-yl (methyl) phosphinic acid (hereinafter abbreviated as compound B), 2-amino-4-[(hydroxy) (methyl) phosphinoyl] butyrylalanylalanine (hereinafter abbreviated as compound C), N-
An improved herbicidal composition comprising, as an active ingredient, at least one selected from the group consisting of (phosphonomethyl) glycine (hereinafter abbreviated as compound D) and a salt thereof, and an inorganic magnesium salt. To a herbicidal composition that has been made.

【0002】[0002]

【従来技術】本願出願人は、化合物A又はその塩と化合
物B、C、D及びそれらの塩から成る群より選ばれた少
なくとも1種とを有効成分とすることを特徴とする除草
組成物を先に出願している(特願平3−132444号
及び同3−308558号)が、該出願には本願発明の
特徴である無機マグネシウム塩添加についての記載はな
い。
BACKGROUND OF THE INVENTION The applicant of the present invention has prepared a herbicidal composition comprising a compound A or a salt thereof and at least one compound selected from the group consisting of compounds B, C, D and salts thereof as active ingredients. Although the application has been filed earlier (Japanese Patent Application Nos. 3-132444 and 3-308558), there is no description in this application regarding the addition of an inorganic magnesium salt which is a feature of the present invention.

【0003】[0003]

【発明の開示】本願発明者等は、本願出願人が先に出願
した除草組成物の散布液中での安定性及び酸性度の改善
並びに製剤品の安定性について研究を行い、本発明を完
成した。すなわち、本発明は、化合物A又はその塩と化
合物B、C、D及びそれらの塩から成る群より選ばれた
少なくとも1種とを有効成分とする除草組成物に、無機
マグネシウム塩を添加することを特徴とする、改良され
た除草組成物(以下単に除草組成物という)である。
DISCLOSURE OF THE INVENTION The present inventors have conducted studies on the improvement of the stability and acidity of a herbicidal composition previously applied by the present applicant in a spray liquid and the stability of a pharmaceutical product, and completed the present invention. did. That is, the present invention comprises adding an inorganic magnesium salt to a herbicidal composition containing as an active ingredient a compound A or a salt thereof and at least one selected from the group consisting of compounds B, C, D and salts thereof. And an improved herbicidal composition (hereinafter simply referred to as a herbicidal composition).

【0004】本発明の特徴である無機マグネシウム塩の
添加によって改良された点としては、使用する除草性有
効成分によって異なる場合があるが、次のようなことが
挙げられる。まず第1に本発明除草組成物を水で希釈し
て散布液とした場合、除草性有効成分の分解が防止で
き、安定且つ良好な除草効果が得られる。第2には、前
述の散布液が強酸性となる状況下でもこれを中性に改善
することができる場合がある。第3には、本発明の除草
組成物の製剤における吸湿性を抑制し、長期間の保存が
可能となる。
[0004] The points improved by the addition of the inorganic magnesium salt, which is a feature of the present invention, may vary depending on the herbicidal active ingredient used. First, when the herbicidal composition of the present invention is diluted with water to form a spray liquid, decomposition of the herbicidal active ingredient can be prevented, and a stable and good herbicidal effect can be obtained. Secondly, there are cases where the above-mentioned spray liquid can be neutralized even in a situation where it is strongly acidic. Third, hygroscopicity of the formulation of the herbicidal composition of the present invention is suppressed, and long-term storage becomes possible.

【0005】本発明除草組成物の除草性有効成分の1種
である化合物Aの塩としては、ナトリウム、カリウムな
どのアルカリ金属塩、マグネシウム、カルシウムなどの
アルカリ土類金属塩、モノメチルアミン、モノイソプロ
ピルアミン、ジメチルアミン、ジイソプロピルアミン、
トリエチルアミンなどのアミン塩、トリメチルエチルア
ンモニウムカチオン、テトラメチルアンモニウムカチオ
ンなどの第4級アンモニウム塩基の塩などが挙げられ
る。また、化合物B及びCの塩としては、無機又は有機
の塩基との塩が挙げられ、好ましくはナトリウム塩、ア
ンモニウム塩、アルキル置換アンモニウム塩が挙げられ
る。化合物Dの塩としては、化合物Dと塩を形成するも
のであればいずれのものでもよいが、例えば前記化合物
Aの塩と同様のもの、さらにはトリアルキルスルホニウ
ム塩、トリアルキルスルホキソニウム塩、アンモニウム
塩などが挙げられる。
The salts of compound A, which is one of the herbicidal active ingredients of the herbicidal composition of the present invention, include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as magnesium and calcium, monomethylamine and monoisopropyl. Amine, dimethylamine, diisopropylamine,
Examples include amine salts such as triethylamine, and salts of quaternary ammonium bases such as trimethylethylammonium cation and tetramethylammonium cation. Examples of the salts of compounds B and C include salts with inorganic or organic bases, and preferably include sodium salts, ammonium salts, and alkyl-substituted ammonium salts. The salt of the compound D may be any as long as it forms a salt with the compound D. For example, the same as the salt of the compound A, further, a trialkylsulfonium salt, a trialkylsulfoxonium salt, Ammonium salts and the like.

【0006】本発明除草組成物において、化合物A又は
その塩と混合することが望ましい除草性有効成分として
は、化合物B(一般名:グルホシネート)、化合物Bの
アンモニウム塩(一般名:グルホシネートのアンモニウ
ム塩)、化合物Cのナトリウム塩(一般名:ビアラホス
のナトリウム塩)、化合物Dのイソプロピルアミン塩
(一般名:グリホサートのイソプロピルアミン塩)、化
合物Dのトリメチルスルホニウム塩(一般名:グリホサ
ートのトリメシウム塩)、化合物Dのアンモニウム塩
(一般名:グリホサートのアンモニウム塩)が挙げられ
る。
In the herbicidal composition of the present invention, as the herbicidal active ingredient which is desirably mixed with compound A or a salt thereof, compound B (generic name: glufosinate), an ammonium salt of compound B (generic name: ammonium salt of glufosinate) ), Sodium salt of compound C (generic name: sodium salt of bialaphos), isopropylamine salt of compound D (generic name: isopropylamine salt of glyphosate), trimethylsulfonium salt of compound D (generic name: trimesium salt of glyphosate), An ammonium salt of the compound D (generic name: ammonium salt of glyphosate) may be mentioned.

【0007】本発明除草組成物の除草性有効成分に含ま
れる化合物B、化合物Bの塩、化合物C及び化合物Cの
塩は、光学異性体を含むものであり、例えばDL−ホモ
アラニン−4−イル(メチル)ホスフィン酸(以下化合
物BのDL体と略す)、L−ホモアラニン−4−イル
(メチル)ホスフィン酸(以下化合物BのL体と略
す)、L−2−アミノ−4−〔(ヒドロキシ)(メチ
ル)ホスフィノイル〕ブチリル−L−アラニル−L−ア
ラニン(以下化合物CのL体と略す)などが挙げられ
る。
The compound B, the salt of the compound B, the compound C and the salt of the compound C contained in the herbicidal active ingredient of the herbicidal composition of the present invention contain optical isomers, for example, DL-homoalanin-4-yl. (Methyl) phosphinic acid (hereinafter abbreviated as DL-form of compound B), L-homoalanin-4-yl (methyl) phosphinic acid (hereinafter abbreviated as L-form of compound B), L-2-amino-4-[(hydroxy ) (Methyl) phosphinoyl] butyryl-L-alanyl-L-alanine (hereinafter abbreviated as L-form of compound C).

【0008】本発明に含まれる無機マグネシウム塩とし
ては、例えば酸化マグネシウム、炭酸マグネシウム、水
酸化マグネシウム、硫酸マグネシウム、塩化マグネシウ
ム、硝酸マグネシウムなどが挙げられる。これらの添加
により本発明除草組成物を水で希釈して散布液とした場
合、除草性有効成分の1つである化合物Aの分解が抑制
される。また、前述の散布液が強酸性となる状況下にお
いては、酸化マグネシウム、炭酸マグネシウム、水酸化
マグネシウムなどの添加によって中性に改善することも
できる為、人体や周辺環境に対する悪影響、散布器具の
腐食等の問題が解決できる。散布液が強酸性となる除草
組成物としては、例えば化合物Aと、化合物B、C及び
Dより選ばれた少なくとも1種との組合せのものが挙げ
られる。一方、本発明除草組成物を製剤(例えば水和剤
に製剤)した場合、炭酸マグネシウム、硫酸マグネシウ
ムなどの添加によって吸湿性を抑制することもできる
為、長期間の保存が可能になる。製剤品が吸湿性を帯び
る除草組成物としては、例えば化合物A又はその塩と、
化合物Bの塩、化合物Cの塩及び化合物Dの塩より選ば
れた少なくとも1種との組合せのものが挙げられる。
The inorganic magnesium salts included in the present invention include, for example, magnesium oxide, magnesium carbonate, magnesium hydroxide, magnesium sulfate, magnesium chloride, magnesium nitrate and the like. When the herbicidal composition of the present invention is diluted with water to give a spray liquid by these additions, the decomposition of Compound A, which is one of the herbicidal active ingredients, is suppressed. In addition, in the situation where the above-mentioned spray liquid is strongly acidic, it can be improved to neutrality by adding magnesium oxide, magnesium carbonate, magnesium hydroxide, etc. And other problems can be solved. Examples of the herbicidal composition in which the spray liquid is strongly acidic include, for example, a combination of compound A and at least one selected from compounds B, C and D. On the other hand, when the herbicidal composition of the present invention is formulated (for example, formulated in a wettable powder), the hygroscopicity can be suppressed by adding magnesium carbonate, magnesium sulfate, etc., so that long-term storage becomes possible. As the herbicidal composition in which the pharmaceutical product is hygroscopic, for example, compound A or a salt thereof,
Examples thereof include a combination with at least one selected from a salt of compound B, a salt of compound C and a salt of compound D.

【0009】本発明除草組成物は、化合物A又はその塩
と、化合物B、C、D及びそれらの塩から成る群より選
ばれた少なくとも1種並びに無機マグネシウム塩とを、
通常の農薬の製剤方法に準じて各種補助剤と必要に応じ
て配合し、水和剤、粉剤、微粒剤、顆粒水和剤、油性懸
濁剤などの形態に製剤して調製されるが、その際前述の
各成分を一緒に混合、製剤してもよく、或いは別々に製
剤後それらを混合してもよい。
The herbicidal composition of the present invention comprises a compound A or a salt thereof, at least one compound selected from the group consisting of compounds B, C, D and salts thereof, and an inorganic magnesium salt.
It is prepared by formulating in the form of wettable powders, powders, fine granules, wettable granules, oily suspensions, etc. In that case, the above-mentioned components may be mixed and formulated together, or they may be mixed separately after formulation.

【0010】前記補助剤としては、珪藻土、消石灰、炭
酸カルシウム、滑石、ホワイトカーボン、カオリン、ベ
ントナイト、ジークライト、水溶性デンプン、炭酸ナト
リウム、重曹、芒硝、硫酸アンモニウムなどの固形担
体;エチレングリコール、プロピレングリコールなどの
凍結防止剤;アルキルスルホン酸塩、アルコール硫酸エ
ステル塩、アルキルベンゼンスルホン酸塩、リグニンス
ルホン酸塩、ジアルキルタウリン酸塩、脂肪アルコール
硫酸塩、ポリオキシエチレングリコールアルキルエーテ
ル、ポリオキシエチレンラウリルエーテル、ポリオキシ
エチレンアルキルアリールエーテル、ポリオキシエチレ
ン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪
酸エステル、ポリオキシエチレンスチリルフェニルエー
テル、ポリカルボン酸塩、ジアルキルスルホコハク酸
塩、アルキルジグリコールエーテル硫酸塩、ポリオキシ
エチレンアルキルアリールエーテル硫酸塩、ポリオキシ
エチレンアルキルアリール燐酸エステル塩、ポリオキシ
エチレン硬化ひまし油、スチリルフェニル燐酸塩、ナフ
タレンスルホン酸塩とホルマリンの縮合物、安息香酸塩
などの展着剤や界面活性剤;オリーブ油、カポック油、
ひまし油、パパヤ油、椿油、ヤシ油、ごま油、トウモロ
コシ油、米ぬか油、落花生油、棉実油、大豆油、菜種
油、亜麻仁油、きり油、液状パラフィンなどの植物油や
鉱物油;プロピレングリコールモノメチルエーテルのよ
うな溶剤;アルミニウムマグネシウムケイ酸、有機化ベ
ントナイト等の沈降防止剤、ザンサンガム等の増粘剤な
どが挙げられる。前記補助剤は必要に応じて混合しても
よい。
Examples of the auxiliary include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, siegrite, water-soluble starch, sodium carbonate, sodium bicarbonate, sodium sulfate and ammonium sulfate; ethylene glycol, propylene glycol Antifreezing agents such as alkyl sulfonate, alcohol sulfate, alkylbenzene sulfonate, lignin sulfonate, dialkyl taurate, fatty alcohol sulfate, polyoxyethylene glycol alkyl ether, polyoxyethylene lauryl ether, poly Oxyethylene alkyl aryl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene styryl phenyl ether, polycarboxylic Salt, dialkyl sulfosuccinate, alkyl diglycol ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl phosphate, polyoxyethylene hydrogenated castor oil, styrylphenyl phosphate, naphthalene sulfonate and formalin Spreading agents and surfactants such as condensates and benzoates; olive oil, kapok oil,
Castor oil, papaya oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, cutting oil, vegetable oil and mineral oil such as liquid paraffin; propylene glycol monomethyl ether Examples of such a solvent include anti-settling agents such as aluminum magnesium silicic acid and organic bentonite, and thickeners such as xanthan gum. The adjuvants may be mixed as needed.

【0011】本発明除草組成物の製剤における各成分の
配合割合は、製剤全体を基準に重量比で表わすと、除草
性有効成分が1〜90%、望ましくは10〜70%であ
り、無機マグネシウム塩が5〜85%、望ましくは5〜
40%であり、固形担体が0〜85%、望ましくは0〜
40%であり、界面活性剤が1〜60%、望ましくは1
0〜50%である。
The proportion of each component in the preparation of the herbicidal composition of the present invention is 1 to 90%, preferably 10 to 70% of the herbicidal active ingredient, expressed as a weight ratio based on the whole preparation. 5 to 85% salt, preferably 5 to
40%, and the solid carrier is 0 to 85%, preferably 0 to 85%.
40%, and 1-60% of a surfactant, preferably 1
0 to 50%.

【0012】[0012]

【実施例】次に本発明除草組成物の製剤例を記載するが
製剤例はこれらのみに限定されるものではない。 製剤例1. (1)化合物A(純度95%)・・・5.42重量部 (2)化合物BのDL体(純度84.6%)・・・5
4.1重量部 (3)ジオクチルスルホサクシネートのナトリウム塩と
安息香酸のナトリウム塩との混合物(商品名:ニューカ
ルゲンEX−70;竹本油脂(株)製)・・・20.0
重量部 (4)炭酸マグネシウム・・・20.0重量部 (5)芒硝・・・0.48重量部 以上の成分を混合し、水和剤を得た。
EXAMPLES Next, formulation examples of the herbicidal composition of the present invention will be described, but the formulation examples are not limited thereto. Formulation Example 1 (1) Compound A (purity 95%) ··· 5.42 parts by weight (2) DL form of compound B (purity 84.6%) ··· 5
4.1 parts by weight (3) Mixture of sodium salt of dioctyl sulfosuccinate and sodium salt of benzoic acid (trade name: Newcalgen EX-70; manufactured by Takemoto Yushi Co., Ltd.) 20.0
Parts by weight (4) Magnesium carbonate: 20.0 parts by weight (5) Glauberite: 0.48 parts by weight The above components were mixed to obtain a wettable powder.

【0013】製剤例2 前記製剤例1において、炭酸マグネシウム20.0重量
部を硫酸マグネシウム10.0重量部に変え、芒硝0.
48重量部を10.48重量部に変える以外は製剤例1
と同様にして水和剤を得た。
Formulation Example 2 In Formulation Example 1, 20.0 parts by weight of magnesium carbonate was changed to 10.0 parts by weight of magnesium sulfate.
Formulation Example 1 except changing 48 parts by weight to 10.48 parts by weight
In the same manner as in the above, a wettable powder was obtained.

【0014】製剤例3 前記製剤例2において、硫酸マグネシウムを酸化マグネ
シウムに変える以外は製剤例2と同様にして水和剤を得
た。
Formulation Example 3 A wettable powder was obtained in the same manner as in Formulation Example 2 except that magnesium sulfate was changed to magnesium oxide.

【0015】製剤例4 前記製剤例2において、硫酸マグネシウムを水酸化マグ
ネシウムに変える以外は製剤例2と同様にして水和剤を
得た。
Formulation Example 4 A wettable powder was obtained in the same manner as in Formulation Example 2 except that magnesium sulfate was changed to magnesium hydroxide.

【0016】製剤例5 (1)化合物A(純度95%)・・・5.42重量部 (2)化合物BのDL体のアンモニウム塩(純度98.
6%)・・・52.15重量部 (3)ニューカルゲンEX−70(商品名)・・・2
0.0重量部 (4)炭酸マグネシウム・・・22.43重量部 以上の成分を混合し、水和剤を得た。
Formulation Example 5 (1) Compound A (purity: 95%): 5.42 parts by weight (2) Ammonium salt of DL form of compound B (purity: 98.95%)
5% by weight (3) New Calgen EX-70 (trade name) 2
0.0 parts by weight (4) Magnesium carbonate 22.43 parts by weight The above components were mixed to obtain a wettable powder.

【0017】製剤例6 前記製剤例5において、炭酸マグネシウムを酸化マグネ
シウムに変える以外は製剤例5と同様にして水和剤を得
た。
Formulation Example 6 A wettable powder was obtained in the same manner as in Formulation Example 5 except that magnesium carbonate was changed to magnesium oxide.

【0018】製剤例7 (1)化合物A(純度95%)・・・5.42重量部 (2)化合物BのDL体(純度85%)・・・54.1
重量部 (3)ニューカルゲンEX−70(商品名)・・・2
0.0重量部 (4)炭酸マグネシウム・・・20.48重量部 以上の成分を混合し、水和剤を得た。
Formulation Example 7 (1) Compound A (purity: 95%): 5.42 parts by weight (2) DL form of compound B (purity: 85%): 54.1
Parts by weight (3) New Calgen EX-70 (brand name) ... 2
0.0 parts by weight (4) Magnesium carbonate 20.48 parts by weight The above components were mixed to obtain a wettable powder.

【0019】製剤例8 (1)化合物A(純度95%)・・・5.42重量部 (2)化合物BのDL体(純度85%)・・・54.1
重量部 (3)ニューカルゲンEX−70(商品名)・・・2
0.0重量部 (4)酸化マグネシウム・・・5.0重量部 (5)硫酸アンモニウム・・・15.48重量部 以上の成分を混合し、水和剤を得た。
Formulation Example 8 (1) Compound A (purity: 95%): 5.42 parts by weight (2) DL form of compound B (purity: 85%): 54.1
Parts by weight (3) New Calgen EX-70 (brand name) ... 2
0.0 parts by weight (4) Magnesium oxide ... 5.0 parts by weight (5) Ammonium sulfate ... 15.48 parts by weight The above components were mixed to obtain a wettable powder.

【0020】製剤例9 前記製剤例8において、酸化マグネシウム5.0重量部
を水酸化マグネシウム10.0重量部に変え、硫酸アン
モニウム15.48重量部を10.48重量部に変える
以外は製剤例8と同様にして水和剤を得た。
Formulation Example 9 Formulation Example 8 is the same as Formulation Example 8 except that 5.0 parts by weight of magnesium oxide is changed to 10.0 parts by weight of magnesium hydroxide and 15.48 parts by weight of ammonium sulfate is changed to 10.48 parts by weight. In the same manner as in the above, a wettable powder was obtained.

【0021】製剤例10 (1)化合物A・・・2重量部 (2)化合物CのL体のナトリウム塩・・・40重量部 (3)ニューカルゲンEX−70(商品名)・・・30
重量部 (4)炭酸マグネシウム・・・20重量部 (5)芒硝・・・8重量部 以上の成分を混合し、水和剤を得る。
Formulation Example 10 (1) Compound A: 2 parts by weight (2) L-form sodium salt of compound C: 40 parts by weight (3) Newcalgen EX-70 (trade name): 30
Parts by weight (4) Magnesium carbonate 20 parts by weight (5) Glauberite 8 parts by weight The above components are mixed to obtain a wettable powder.

【0022】製剤例11 (1)化合物A・・・2重量部 (2)化合物Dのイソプロピルアミン塩・・・40重量
部 (3)アルキルスルホン酸ナトリウム(商品名:Wet
ting agent−IS;ヘキスト社製)・・・3
0重量部 (4)炭酸マグネシウム・・・20重量部 (5)芒硝・・・8重量部 以上の成分を混合し、水和剤を得る。
Formulation Example 11 (1) Compound A: 2 parts by weight (2) Isopropylamine salt of compound D: 40 parts by weight (3) Sodium alkyl sulfonate (trade name: Wet)
(ting agent-IS; manufactured by Hoechst) 3
0 parts by weight (4) Magnesium carbonate 20 parts by weight (5) Glauberite 8 parts by weight The above components are mixed to obtain a wettable powder.

【0023】製剤例12 (1)化合物A・・・2重量部 (2)化合物Dのトリメチルスルホニウム塩・・・40
重量部 (3)ニューカルゲンEX−70(商品名)・・・30
重量部 (4)炭酸マグネシウム・・・20重量部 (5)芒硝・・・8重量部 以上の成分を混合し、水和剤を得る。
Formulation Example 12 (1) Compound A ... 2 parts by weight (2) Compound D trimethylsulfonium salt ... 40
Parts by weight (3) New Calgen EX-70 (trade name) ... 30
Parts by weight (4) Magnesium carbonate 20 parts by weight (5) Glauberite 8 parts by weight The above components are mixed to obtain a wettable powder.

【0024】製剤例13 (1)化合物A・・・2重量部 (2)化合物Dのアンモニウム塩・・・40重量部 (3)Wetting agent−IS(商品名)・
・・30重量部 (4)炭酸マグネシウム・・・20重量部 (5)芒硝・・・8重量部 以上の成分を混合し、水和剤を得る。
Formulation Example 13 (1) Compound A: 2 parts by weight (2) Ammonium salt of compound D: 40 parts by weight (3) Wetting agent-IS (trade name)
.... 30 parts by weight (4) Magnesium carbonate ... 20 parts by weight (5) Glauber's salt ... 8 parts by weight The above components are mixed to obtain a wettable powder.

【0025】製剤例14 (1)化合物Aのナトリウム塩・・・2.1重量部 (2)化合物BのDL体・・・40重量部 (3)ニューカルゲンEX−70(商品名)・・・30
重量部 (4)炭酸マグネシウム・・・20重量部 (5)芒硝・・・7.9 重量部 以上の成分を混合し、水和剤を得る。
Formulation Example 14 (1) Sodium salt of compound A: 2.1 parts by weight (2) DL form of compound B: 40 parts by weight (3) Newcargen EX-70 (trade name)・ 30
Parts by weight (4) Magnesium carbonate 20 parts by weight (5) Glauberite 7.9 parts by weight The above components are mixed to obtain a wettable powder.

【0026】製剤例15 (1)化合物A・・・5重量部 (2)化合物BのDL体・・・55重量部 (3)ニューカルゲンEX−70(商品名)・・・20
重量部 (4)炭酸マグネシウム・・・10重量部 (5)芒硝・・・10重量部 以上の成分を3倍量の水に懸濁させ、スプレードライ法
で乾燥して、顆粒水和剤を得る。
Formulation Example 15 (1) Compound A: 5 parts by weight (2) DL form of Compound B: 55 parts by weight (3) Newcalgen EX-70 (trade name): 20
Parts by weight (4) Magnesium carbonate 10 parts by weight (5) Glauberite 10 parts by weight The above components are suspended in 3 times the amount of water, and dried by a spray drying method to obtain a wettable powder for granules. obtain.

【0027】製剤例16 (1)化合物A・・・0.8重量部 (2)化合物BのDL体・・・14.7重量部 (3)ポリカルボン酸金属塩(商品名:ニューカルゲン
WG−5;竹本油脂(株)製)・・・5.0重量部 (4)アルキルナフタレンスルホン酸金属塩(商品名:
ニューカルゲンWG−1;竹本油脂(株)製)・・・
5.0重量部 (5)リグニンスルホン酸ナトリウム塩・・・5.0重
量部 (6)炭酸マグネシウム・・・20.0重量部 (7)ベントナイト(60〜150メッシュ)・・・4
9.5 重量部 以上の成分を混合し、微粒剤を得る。
Formulation Example 16 (1) Compound A: 0.8 parts by weight (2) DL form of compound B: 14.7 parts by weight (3) Metal polycarboxylate (trade name: Neucalgen WG) -5; manufactured by Takemoto Yushi Co., Ltd.) 5.0 parts by weight (4) Metal salt of alkylnaphthalenesulfonic acid (trade name:
New Calgen WG-1; manufactured by Takemoto Yushi Co., Ltd.)
5.0 parts by weight (5) Lignin sulfonic acid sodium salt ... 5.0 parts by weight (6) Magnesium carbonate ... 20.0 parts by weight (7) Bentonite (60-150 mesh) ... 4
9.5 parts by weight The above components are mixed to obtain a fine granule.

【0028】製剤例17 (1)化合物A・・・0.8重量部 (2)化合物BのDL体・・・14.7重量部 (3)ドデシルベンゼンスルホン酸のナトリウム塩と芒
硝の混合物(商品名:ニューカルゲンSX−C;竹本油
脂(株)製)・・・5.0重量部 (4)ニューカルゲンEX−70(商品名)・・・3
0.0 重量部 (5)炭酸マグネシウム・・・10.0 重量部 (6)炭酸カルシウム・・・39.5 重量部 以上の成分を混合し、粉剤を得る。
Formulation Example 17 (1) Compound A: 0.8 parts by weight (2) DL form of compound B: 14.7 parts by weight (3) Mixture of sodium salt of dodecylbenzenesulfonic acid and sodium sulfate ( Trade name: New Cargen SX-C; manufactured by Takemoto Yushi Co., Ltd.) 5.0 parts by weight (4) New Cargen EX-70 (trade name) 3
0.0 parts by weight (5) Magnesium carbonate: 10.0 parts by weight (6) Calcium carbonate: 39.5 parts by weight The above components are mixed to obtain a powder.

【0029】製剤例18 (1)化合物A(純度95%)・・・1.43重量部 (2)化合物BのDL体(純度73%)・・・34.8
重量部 (3)ニューカルゲンEX−70(商品名)・・・3
8.1重量部 (4)ニューカルゲンSX−C(商品名)・・・2.0
重量部 (5)硫酸マグネシウム・・・15.0 重量部 (6)硫酸アンモニウム・・・7.17 重量部 (7)n−パラフィン(試作品90066;竹本油脂
(株)製)・・・1.5重量部 以上の成分を混合し、水和剤を得た。
Formulation Example 18 (1) Compound A (purity 95%): 1.43 parts by weight (2) DL form of compound B (purity 73%): 34.8
Parts by weight (3) New Calgen EX-70 (brand name) ... 3
8.1 parts by weight (4) New Calgen SX-C (trade name) 2.0
Parts by weight (5) Magnesium sulfate: 15.0 parts by weight (6) Ammonium sulfate: 7.17 parts by weight (7) n-paraffin (prototype 90066; manufactured by Takemoto Yushi Co., Ltd.) 5 parts by weight or more of the components were mixed to obtain a wettable powder.

【0030】製剤例19 前記製剤例18において、ニューカルゲンSX−C(商
品名)を脂肪アルコール硫酸のナトリウム塩(商品名:
ニューカルゲン204;竹本油脂(株)製)に変える以
外は製剤例18と同様にして水和剤を得た。
Formulation Example 19 In Formulation Example 18, Newcargen SX-C (trade name) was replaced with sodium salt of fatty alcohol sulfuric acid (trade name:
A wettable powder was obtained in the same manner as in Formulation Example 18 except that the composition was changed to Newcalgen 204; Takemoto Yushi Co., Ltd.).

【0031】製剤例20 前記製剤例18において、ニューカルゲンSX−C(商
品名)をナフタリンスルホン酸ナトリウム縮合物(商品
名:ニューカルゲンPS−P;竹本油脂(株)製)に変
える以外は製剤例18と同様にして水和剤を得た。
Formulation Example 20 The same procedures as in Formulation Example 18 except that Newcargen SX-C (trade name) is changed to sodium naphthalenesulfonate condensate (trade name: Newcargen PS-P; manufactured by Takemoto Yushi Co., Ltd.) A wettable powder was obtained in the same manner as in Example 18.

【0032】製剤例21 前記製剤例18において、ニューカルゲンSX−C(商
品名)をナフタリンスルホン酸ナトリウム縮合物とジオ
クチルスルホコハク酸のナトリウム塩との混合物(商品
名:ニューカルゲンPX−510;竹本油脂(株)製)
に変える以外は製剤例18と同様にして水和剤を得た。
Formulation Example 21 In Formulation Example 18, a mixture of Newcargen SX-C (trade name) with sodium naphthalenesulfonate condensate and sodium salt of dioctylsulfosuccinic acid (trade name: Newcalgen PX-510; Takemoto Yushi) (Made by Corporation)
A wettable powder was obtained in the same manner as in Preparation Example 18 except that

【0033】製剤例22 (1)化合物A(純度95%)・・・1.43重量部 (2)化合物BのDL体(純度73%)・・・34.8
重量部 (3)ニューカルゲンEX−70(商品名)・・・3
8.1重量部 (4)ニューカルゲンSX−C(商品名)・・・4.0
重量部 (5)硫酸マグネシウム・・・15.0 重量部 (6)硫酸アンモニウム・・・5.17 重量部 (7)n−パラフィン(商品名:ドリレスC;三共
(株)製)・・・1.5重量部 以上の成分を混合し、水和剤を得る。
Formulation Example 22 (1) Compound A (purity: 95%): 1.43 parts by weight (2) DL form of Compound B (purity: 73%): 34.8
Parts by weight (3) New Calgen EX-70 (brand name) ... 3
8.1 parts by weight (4) New Calgen SX-C (brand name) ... 4.0
Parts by weight (5) Magnesium sulfate ... 15.0 parts by weight (6) Ammonium sulfate ... 5.17 parts by weight (7) n-paraffin (trade name: Drilles C; manufactured by Sankyo Co., Ltd.) ... 1 The above components are mixed to obtain a wettable powder.

【0034】製剤例23 (1)化合物A(純度95%)・・・1.43重量部 (2)化合物BのDL体(純度73%)・・・34.8
重量部 (3)ニューカルゲンEX−70(商品名)・・・3
8.1重量部 (4)硫酸マグネシウム・・・15.0 重量部 (5)硫酸アンモニウム・・・9.17 重量部 (6)試作品90066(同前)・・・1.5重量部 以上の成分を混合し、水和剤を得た。
Formulation Example 23 (1) Compound A (purity: 95%): 1.43 parts by weight (2) DL form of Compound B (purity: 73%): 34.8
Parts by weight (3) New Calgen EX-70 (brand name) ... 3
8.1 parts by weight (4) Magnesium sulfate: 15.0 parts by weight (5) Ammonium sulfate: 9.17 parts by weight (6) Prototype 90066 (same as above): 1.5 parts by weight The components were mixed to obtain a wettable powder.

【0035】製剤例24 (1)化合物A(純度95%)・・・3.5重量部 (2)化合物BのDL体(純度73%)・・・62.6
重量部 (3)ニューカルゲンEX−70(商品名)・・・2
0.0重量部 (4)ニューカルゲンSX−C(商品名)・・・2.0
重量部 (5)硫酸マグネシウム・・・10.4 重量部 (6)試作品90066(同前)・・・1.5重量部 以上の成分を混合し、水和剤を得た。
Formulation Example 24 (1) Compound A (purity: 95%): 3.5 parts by weight (2) DL form of compound B (purity: 73%): 62.6
Parts by weight (3) New Calgen EX-70 (brand name) ... 2
0.0 parts by weight (4) New Calgen SX-C (trade name) 2.0
Parts by weight (5) Magnesium sulfate ... 10.4 parts by weight (6) Prototype 90066 (same as above) ... 1.5 parts by weight The above components were mixed to obtain a wettable powder.

【0036】製剤例25 (1)化合物A(純度95%)・・・5.26重量部 (2)化合物BのDL体(純度73%)・・・62.6
重量部 (3)ニューカルゲンEX−70(商品名)・・・1
5.0重量部 (4)ニューカルゲン204(商品名)・・・2.0重
量部 (5)硫酸マグネシウム・・・10.0 重量部 (6)硫酸アンモニウム・・・3.64 重量部 (7)試作品90066(同前)・・・1.5重量部 以上の成分を混合し、水和剤を得た。
Formulation Example 25 (1) Compound A (purity 95%): 5.26 parts by weight (2) DL form of Compound B (purity 73%) 62.6
Parts by weight (3) New Calgen EX-70 (trade name) 1
5.0 parts by weight (4) Newcalgen 204 (trade name) ... 2.0 parts by weight (5) Magnesium sulfate ... 10.0 parts by weight (6) Ammonium sulfate ... 3.64 parts by weight (7 ) Prototype 90066 (same as above): 1.5 parts by weight The above components were mixed to obtain a wettable powder.

【0037】製剤例26 前記製剤例18において、ニューカルゲンSX−C(商
品名)をアルコール硫酸エステルのナトリウム塩(商品
名:モノゲンY−500;第一工業製薬(株)製)に変
える以外は製剤例18と同様にして水和剤を得た。
Formulation Example 26 Preparation Example 18 is the same as Formulation Example 18 except that Newcargen SX-C (trade name) is changed to a sodium salt of alcohol sulfate (trade name: Monogen Y-500; manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.). A wettable powder was obtained in the same manner as in Formulation Example 18.

【0038】製剤例27 前記製剤例18において、ニューカルゲンSX−C(商
品名)をナフタレンスルホン酸のナトリウム塩とホルマ
リンの縮合物(商品名:ラベリンFAN;第一工業製薬
(株)製)に変える以外は製剤例18と同様にして水和
剤を得た。
Formulation Example 27 In Formulation Example 18, Newcargen SX-C (trade name) was converted to a condensate of sodium salt of naphthalenesulfonic acid and formalin (trade name: Labelin FAN; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.). A wettable powder was obtained in the same manner as in Preparation Example 18, except that the composition was changed.

【0039】製剤例28 前記製剤例18において、ニューカルゲンSX−C(商
品名)を混合アニオン活性剤(商品名:Dispers
ing agent SI;ヘキスト社製)に変える以
外は製剤例18と同様にして水和剤を得た。
Formulation Example 28 In Formulation Example 18, Newcargen SX-C (trade name) was mixed with a mixed anion activator (trade name: Dispers)
ing agent SI (manufactured by Hoechst)), and a wettable powder was obtained in the same manner as in Preparation Example 18.

【0040】製剤例29 前記製剤例18において、ニューカルゲンSX−C(商
品名)をオレイルメチルタウリン酸のナトリウム塩(商
品名:Hostapon T;ヘキスト社製)に変える
以外は製剤例18と同様にして水和剤を得た。
Formulation Example 29 Preparation Example 18 was carried out in the same manner as in Formulation Example 18 except that Newcalgen SX-C (trade name) was changed to sodium salt of oleylmethyltauric acid (trade name: Hostapon T; manufactured by Hoechst AG). To obtain a wettable powder.

【0041】比較製剤例1 (1)化合物A(純度95%)・・・5.42重量部 (2)化合物BのDL体(純度70%)・・・66.7
重量部 (3)Wetting agent−IS(商品名)・
・・20.0重量部 (4)硫酸アンモニウム・・・7.88重量部 以上の成分を混合し、水和剤を得た。
Comparative Preparation Example 1 (1) Compound A (purity: 95%): 5.42 parts by weight (2) DL form of compound B (purity: 70%): 66.7
Parts by weight (3) Wetting agent-IS (trade name)
20.0 parts by weight (4) Ammonium sulfate: 7.88 parts by weight The above components were mixed to obtain a wettable powder.

【0042】比較製剤例2 (1)化合物A(純度95%)・・・5.42重量部 (2)化合物BのDL体のアンモニウム塩(純度98.
6%)・・・52.15重量部 (3)ニューカルゲンEX−70(商品名)・・・2
0.0重量部 (4)硫酸アンモニウム・・・22.43重量部 以上の成分を混合し、水和剤を得た。
Comparative Preparation Example 2 (1) Compound A (purity 95%): 5.42 parts by weight (2) Ammonium salt of DL form of Compound B (purity 98.
5% by weight (3) New Calgen EX-70 (trade name) 2
0.0 parts by weight (4) Ammonium sulfate 22.43 parts by weight The above components were mixed to obtain a wettable powder.

【0043】比較製剤例3 (1)化合物A(純度95%)・・・5.42重量部 (2)化合物BのDL体(純度85%)・・・54.1
重量部 (3)ニューカルゲンEX−70(商品名)・・・2
0.0重量部 (4)硫酸アンモニウム・・・20.48重量部 以上の成分を混合し、水和剤を得た。
Comparative Preparation Example 3 (1) Compound A (purity: 95%): 5.42 parts by weight (2) DL form of compound B (purity: 85%): 54.1
Parts by weight (3) New Calgen EX-70 (brand name) ... 2
0.0 parts by weight (4) Ammonium sulfate ... 20.48 parts by weight The above components were mixed to obtain a wettable powder.

【0044】試験例1 (化合物Aの分解率)前記製剤例及び比較製剤例で得た
水和剤500mgに蒸留水500mlを加え25〜30
℃の恒温下、150r.p.m/minの回転速度で攪
拌し、24時間後に除草性有効成分である化合物Aの分
解率(経時変化率)を液体クロマトグラフ分析により求
めた。その結果を第1表に示す。
Test Example 1 (Decomposition rate of compound A) 500 ml of distilled water was added to 500 mg of the wettable powder obtained in the above Formulation Examples and Comparative Formulation Examples, and 25 to 30 were added.
At a constant temperature of 150 ° C. p. The mixture was stirred at a rotation speed of m / min, and after 24 hours, the decomposition rate (rate of change over time) of the herbicidal active ingredient Compound A was determined by liquid chromatography analysis. Table 1 shows the results.

【0045】[0045]

【表1】 [Table 1]

【0046】試験例2 (製剤品の吸湿率)前記製剤例及び比較製剤例で得た水
和剤1gを、内容量30mlの秤量びんに入れ、それを
相対湿度70%に保持した恒湿デシケーター中に入れ定
期毎に秤量し、恒量(最大限の吸湿)値として、次式よ
り求めた吸湿率及び恒量値に達するまでに要した時間を
求めた。その結果を第2表に示す。
Test Example 2 (Hygroscopicity of Formulation Product) 1 g of the wettable powder obtained in each of the above Formulation Examples and Comparative Formulation Examples was placed in a 30 ml weighing bottle, and the desiccator was kept at a relative humidity of 70%. It was weighed periodically and weighed, and as a constant weight (maximum moisture absorption) value, the moisture absorption rate calculated by the following formula and the time required to reach the constant weight value were determined. Table 2 shows the results.

【0047】[0047]

【表2】 [Table 2]

【0048】試験例3 (化合物Aの分解率)前記試験例1に準じた方法で、次
の各試験サンプルについて化合物Aの分解率を求めた。
その結果を第3表に示す。
Test Example 3 (Decomposition rate of Compound A) The decomposition rate of Compound A was determined for each of the following test samples by the method according to Test Example 1.
Table 3 shows the results.

【0049】試験サンプルNo.1 (1)化合物A(純度95%)・・・0.54重量部 (2)ラウンドアップ(商品名,モンサント社;化合物
Dのイソプロピルアミン塩を41%、水及び界面活性剤
等を59%含有)・・・24.6 重量部 (3)炭酸マグネシウム・・・4.0 重量部 以上の成分を混合し、サンプルを得た。
Test sample No. 1 (1) Compound A (purity 95%): 0.54 parts by weight (2) Round-up (trade name, Monsanto Co .; 41% isopropylamine salt of compound D, 59% water and surfactant etc.) 24.6 parts by weight (3) Magnesium carbonate 4.0 parts by weight The above components were mixed to obtain a sample.

【0050】試験サンプルNo.2 (1)化合物A(純度95%)・・・0.54重量部 (2)タッチダウン(商品名,アイシーアイアメリカズ
社;化合物Dのトリメチルスルホニウム塩を38%、水
及び界面活性剤等を62%含有)・・・26.4 重量
部 (3)炭酸マグネシウム・・・4.0 重量部 以上の成分を混合し、サンプルを得た。
Test sample No. 2 (1) Compound A (purity: 95%): 0.54 parts by weight (2) Touchdown (trade name, ICI Americas; 38% trimethylsulfonium salt of compound D, water, surfactant, etc.) 26.4 parts by weight (3) Magnesium carbonate 4.0 parts by weight The above components were mixed to obtain a sample.

【0051】試験サンプルNo.3 (1)化合物A(純度95%)・・・0.54重量部 (2)草当番(商品名,三共(株)社;化合物Dのアン
モニウム塩を20%、無機塩類、界面活性剤及び色素等
を80%含有)・・・48.4 重量部 (3)炭酸マグネシウム・・・4.0 重量部 以上の成分を混合し、サンプルを得た。
Test sample No. 3 (1) Compound A (purity: 95%): 0.54 parts by weight (2) Herbal Tochiban (trade name, Sankyo Co., Ltd .; 20% of ammonium salt of compound D, inorganic salts, surfactant and 48.4 parts by weight (3) Magnesium carbonate ... 4.0 parts by weight The above components were mixed to obtain a sample.

【0052】[0052]

【表3】 [Table 3]

【0053】試験例4 (酸性度の改善)前記製剤例及び比較製剤例で得た水和
剤を水で1000倍に希釈しpHを測定した。その結果
を第4表に示す。
Test Example 4 (Improvement of Acidity) The wettable powders obtained in the above Formulation Examples and Comparative Formulation Examples were diluted 1000 times with water and the pH was measured. Table 4 shows the results.

【0054】[0054]

【表4】 [Table 4]

【0055】試験例5 (製剤品の吸湿率)前記試験例2と同様にして、前記製
剤例で得た水和剤の吸湿率及び恒量値に達するまでに要
した時間を求めた。その結果を第5表に示す。
Test Example 5 (Moisture Absorption Rate of Formulation Product) In the same manner as in Test Example 2, the moisture absorption rate of the wettable powder obtained in the formulation example and the time required to reach a constant value were determined. Table 5 shows the results.

【0056】[0056]

【表5】 [Table 5]

───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 平5−70313(JP,A) 特開 平4−235106(JP,A) 特開 昭61−267576(JP,A) (58)調査した分野(Int.Cl.7,DB名) A01N 47/36 101 A01N 57/20 CA(STN) REGISTRY(STN)──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-5-70313 (JP, A) JP-A-4-235106 (JP, A) JP-A-61-267576 (JP, A) (58) Investigation Field (Int.Cl. 7 , DB name) A01N 47/36 101 A01N 57/20 CA (STN) REGISTRY (STN)

Claims (3)

(57)【特許請求の範囲】(57) [Claims] 【請求項1】 1−(4,6−ジメトキシピリミジン−
2−イル)−3−(3−トリフルオロメチル−2−ピリ
ジルスルホニル)ウレア又はその塩とホモアラニン−4
−イル(メチル)ホスフィン酸、2−アミノ−4−
〔(ヒドロキシ)(メチル)ホスフィノイル〕ブチリル
アラニルアラニン、N−(ホスホノメチル)グリシン及
びそれらの塩から成る群より選ばれた少なくとも1種と
を有効成分として含有する除草組成物に、無機マグネシ
ウム塩を添加することを特徴とする、改良された除草組
成物。
1. 1- (4,6-dimethoxypyrimidine-
2-yl) -3- (3-trifluoromethyl-2-pyridylsulfonyl) urea or a salt thereof and homoalanine-4
-Yl (methyl) phosphinic acid, 2-amino-4-
An inorganic magnesium salt is added to a herbicidal composition containing, as an active ingredient, at least one selected from the group consisting of [(hydroxy) (methyl) phosphinoyl] butyrylalanylalanine, N- (phosphonomethyl) glycine and a salt thereof. An improved herbicidal composition, characterized by adding:
【請求項2】 (1)1−(4,6−ジメトキシピリミ
ジン−2−イル)−3−(3−トリフルオロメチル−2
−ピリジルスルホニル)ウレア又はその塩、(2)ホモ
アラニン−4−イル(メチル)ホスフィン酸、2−アミ
ノ−4−〔(ヒドロキシ)(メチル)ホスフィノイル〕
ブチリルアラニルアラニン、N−(ホスホノメチル)グ
リシン及びそれらの塩から成る群より選ばれた少なくと
も1種、(3)無機マグネシウム塩及び(4)農薬用補
助剤を含有する除草組成物。
(1) 1- (4,6-dimethoxypyrimi)
Zin-2-yl) -3- (3-trifluoromethyl-2
-Pyridylsulfonyl) urea or a salt thereof, (2) homo
Alanin-4-yl (methyl) phosphinic acid, 2-amido
No-4-[(hydroxy) (methyl) phosphinoyl]
Butyrylalanylalanine, N- (phosphonomethyl)
At least selected from the group consisting of lysine and their salts
(3) inorganic magnesium salt and (4) supplement for pesticides
A herbicidal composition containing an auxiliary.
【請求項3】 農薬用補助剤が固形担体及び界面活性剤
である請求項2の除草組成物。
3. The method according to claim 2, wherein the agricultural chemical auxiliary is a solid carrier and a surfactant.
The herbicidal composition according to claim 2, which is
JP36199592A 1991-12-27 1992-12-25 Improved herbicidal composition Expired - Lifetime JP3253392B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP36199592A JP3253392B2 (en) 1991-12-27 1992-12-25 Improved herbicidal composition

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP3-361431 1991-12-27
JP36143191 1991-12-27
JP36199592A JP3253392B2 (en) 1991-12-27 1992-12-25 Improved herbicidal composition

Publications (2)

Publication Number Publication Date
JPH05271021A JPH05271021A (en) 1993-10-19
JP3253392B2 true JP3253392B2 (en) 2002-02-04

Family

ID=26581265

Family Applications (1)

Application Number Title Priority Date Filing Date
JP36199592A Expired - Lifetime JP3253392B2 (en) 1991-12-27 1992-12-25 Improved herbicidal composition

Country Status (1)

Country Link
JP (1) JP3253392B2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5830827A (en) * 1995-09-21 1998-11-03 Ishihara Sangyo Kaisha, Ltd. Granular herbicidal composition comprising flazasulfuron and a sulfosuccinate or benzoate stabilizer
NZ335586A (en) 1996-10-25 2000-08-25 Monsanto Co Composition and method for treating plants with exogenous chemicals
HU228572B1 (en) 1997-02-05 2013-04-29 Basf Ag Sulphonylurea and/adjuvant based solid mixtures
AU2001253324A1 (en) * 2000-04-13 2001-10-30 Fmc Corporation Safening crops from the phytotoxic effects of herbicidally active n-phosphonomethyl-glycines
DK1825753T3 (en) * 2000-04-26 2014-03-24 Ishihara Sangyo Kaisha Stabilization of solid herbicidal compositions comprising flazasulfuron
JP5000810B2 (en) * 2000-04-26 2012-08-15 石原産業株式会社 Solid herbicidal composition
JP2003192510A (en) * 2001-12-27 2003-07-09 Hodogaya Agros Kk Mixed fine granule containing glyphosate
JP2003192511A (en) * 2001-12-27 2003-07-09 Hodogaya Agros Kk Weed controlling fine granule stable in weather fluctuation
MX2008011232A (en) 2006-03-02 2008-09-11 Ishihara Sangyo Kaisha Solid herbicidal composition.

Also Published As

Publication number Publication date
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