JPH05271021A - Improved weeding composition - Google Patents
Improved weeding compositionInfo
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- JPH05271021A JPH05271021A JP36199592A JP36199592A JPH05271021A JP H05271021 A JPH05271021 A JP H05271021A JP 36199592 A JP36199592 A JP 36199592A JP 36199592 A JP36199592 A JP 36199592A JP H05271021 A JPH05271021 A JP H05271021A
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Abstract
Description
【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 inorganic magnesium salt is added to a herbicidal composition containing, as an active ingredient, at least one selected from the group consisting of (phosphonomethyl) glycine (hereinafter abbreviated as compound D) and salts thereof, and improvement The herbicidal composition.
【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 provides a herbicidal composition comprising compound A or a salt thereof and at least one compound selected from the group consisting of compounds B, C and D and salts thereof as active ingredients. Although previously filed (Japanese Patent Application Nos. 3-132444 and 3-308558), there is no description in the application regarding 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 inventors of the present invention have conducted studies on the stability of herbicidal composition in a spray solution and the improvement of acidity as well as the stability of a preparation, which the applicant of the present invention has previously applied, and completed the present invention. did. That is, the present invention is to add an inorganic magnesium salt to a herbicidal composition containing, as an active ingredient, compound A or a salt thereof and at least one selected from the group consisting of compounds B, C, D and salts thereof. Is 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 differ depending on the herbicidal active ingredient used, but include the following. First of all, when the herbicidal composition of the present invention is diluted with water to give a spray solution, decomposition of the herbicidal active ingredient can be prevented and a stable and good herbicidal effect can be obtained. Secondly, it may be possible to improve the spray liquid to be neutral even under the condition that the spray liquid is strongly acidic. Thirdly, the hygroscopicity of the herbicidal composition formulation of the present invention is suppressed, and the herbicidal composition can be stored for a long period of time.
【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 salt of compound A which is one of the herbicidal active ingredients of the herbicidal composition of the present invention includes alkali metal salts such as sodium and potassium, alkaline earth metal salts such as magnesium and calcium, monomethylamine and monoisopropyl. Amine, dimethylamine, diisopropylamine,
Examples thereof include amine salts such as triethylamine, and salts of quaternary ammonium bases such as trimethylethylammonium cation and tetramethylammonium cation. The salts of compounds B and C include salts with inorganic or organic bases, preferably sodium salts, ammonium salts, and alkyl-substituted ammonium salts. The salt of the compound D may be any salt as long as it forms a salt with the compound D. For example, the same salt as the salt of the compound A, a trialkylsulfonium salt, a trialkylsulfoxonium salt, Examples thereof include ammonium salts.
【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, the herbicidal active ingredient which is preferably mixed with compound A or a salt thereof is compound B (generic name: glufosinate), 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), Examples thereof include the ammonium salt of Compound D (generic name: ammonium salt of glyphosate).
【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 compound B, the compound C and the salt of compound C contained in the herbicidal active ingredient of the herbicidal composition of the present invention include 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) and the like.
【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。Examples of the inorganic magnesium salt included in the present invention include magnesium oxide, magnesium carbonate, magnesium hydroxide, magnesium sulfate, magnesium chloride and magnesium nitrate. By adding these, when the herbicidal composition of the present invention is diluted with water to prepare a spray solution, the decomposition of the compound A, which is one of the herbicidal active ingredients, is suppressed. In addition, under the condition that the spray liquid is strongly acidic, it can be neutralized by adding magnesium oxide, magnesium carbonate, magnesium hydroxide, etc. It can solve such problems. Examples of the herbicidal composition in which the spray solution is strongly acidic include a combination of compound A and at least one compound selected from compounds B, C and D. On the other hand, when the herbicidal composition of the present invention is formulated (for example, in a wettable powder), the hygroscopicity can be suppressed by adding magnesium carbonate, magnesium sulfate, etc., and thus it can be stored for a long period of time. Examples of the herbicidal composition whose preparation has hygroscopicity include Compound A or a salt thereof,
Examples thereof include those in combination with at least one selected from the salt of compound B, the salt of compound C and the 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 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 blending it with various auxiliary agents as necessary according to the usual pesticide formulation method, and formulating into a form such as a wettable powder, a powder, a fine granule, a wettable granule, and an oil suspension. At that time, the above-mentioned respective components may be mixed and formulated together, or they may be separately formulated and then mixed.
【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。As said auxiliary agents, solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, sieglite, water-soluble starch, sodium carbonate, baking soda, mirabilite, ammonium sulfate; ethylene glycol, propylene glycol. Antifreeze agents such as: alkyl sulfonates, alcohol sulfates, alkylbenzene sulfonates, lignin sulfonates, dialkyl taurates, fatty alcohol sulfates, polyoxyethylene glycol alkyl ethers, polyoxyethylene lauryl ethers, poly Oxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene styryl phenyl ether, polycarboxylic acid Salts, dialkyl sulfosuccinates, alkyl diglycol ether sulphates, polyoxyethylene alkyl aryl ether sulphates, polyoxyethylene alkyl aryl phosphates, polyoxyethylene hydrogenated castor oil, styryl phenyl phosphates, naphthalene sulphonates 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, liquid paraffin and other vegetable oils and mineral oils; propylene glycol monomethyl ether Such solvents include aluminum magnesium silicic acid, anti-settling agents such as organized bentonite, thickening agents such as xanthan gum, and the like. The above-mentioned auxiliary agents may be mixed if necessary.
【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 mixing ratio 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 in weight ratio based on the whole preparation, and inorganic magnesium 5 to 85% salt, preferably 5 to 5%
40%, 0-85% solid carrier, preferably 0-
40%, 1 to 60% surfactant, preferably 1
It is 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 to these. Formulation Example 1. (1) Compound A (purity 95%) ... 5.42 parts by weight (2) DL isomer 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) Glauber's salt ... 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 the above Formulation Example 1, 20.0 parts by weight of magnesium carbonate was changed to 10.0 parts by weight of magnesium sulfate, and the amount of Glauber's salt 0.
Formulation Example 1 except that 48 parts by weight was changed to 10.48 parts by weight
A wettable powder was obtained in the same manner as.
【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.
6%) ・ ・ ・ 52.15 parts by weight (3) Newcalgen 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) Newcalgen EX-70 (trade 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) Newcalgen EX-70 (trade 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 except that 5.0 parts by weight of magnesium oxide was changed to 10.0 parts by weight of magnesium hydroxide and 15.48 parts by weight of ammonium sulfate was changed to 10.48 parts by weight. A wettable powder was obtained in the same manner as.
【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) Newkalgen EX-70 (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.
【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
toting agent-IS; manufactured by Hoechst) ... 3
0 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.
【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) Trimethylsulfonium salt of compound D: 40
Parts by weight (3) Newcalgen EX-70 (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.
【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 compound of compound B: 40 parts by weight (3) Newcalgen EX-70 (trade name) ...・ 30
Parts by weight (4) Magnesium carbonate ... 20 parts by weight (5) Glauber's salt ... 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) Compound B DL: 55 parts by weight (3) Newcalgen EX-70 (trade name): 20
Parts by weight (4) Magnesium carbonate: 10 parts by weight (5) Glauber's salt: 10 parts by weight The above components are suspended in 3 times the amount of water and dried by a spray dry method to give a granular wettable powder. 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) Compound B DL: 14.7 parts by weight (3) Polycarboxylic acid metal salt (trade name: Newcalgen WG -5; Takemoto Yushi Co., Ltd .... 5.0 parts by weight (4) Alkylnaphthalenesulfonic acid metal salt (trade name:
Newcalgen 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 to 150 mesh) ... 4
9.5 parts by weight The above ingredients 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) Compound B DL: 14.7 parts by weight (3) Mixture of sodium salt of dodecylbenzenesulfonic acid and Glauber's salt ( Product name: New Kalgen SX-C; Takemoto Yushi Co., Ltd.) 5.0 parts by weight (4) New Kalgen EX-70 (product 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 dust.
【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 Kalgen EX-70 (trade name) ... 3
8.1 parts by weight (4) New Kalgen 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.) ... 1. 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 the above Formulation Example 18, Newcalgen SX-C (trade name) was replaced with sodium salt of fatty alcohol sulfate (trade name:
A wettable powder was obtained in the same manner as in Preparation Example 18 except that Nucargen 204; manufactured by Takemoto Yushi Co., Ltd. was used.
【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 Formulation Example 18 except that Newcalgen SX-C (trade name) is replaced with sodium naphthalenesulfonate condensate (trade name: Newcalgen 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 the above Formulation Example 18, a mixture of Newcalgen SX-C (trade name) with a sodium condensate of naphthalenesulfonate and a sodium salt of dioctylsulfosuccinic acid (trade name: Newcalgen PX-510; Takemoto Yushi) (Made by Co., Ltd.)
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 Kalgen EX-70 (trade name) ... 3
8.1 parts by weight (4) Newkalgen SX-C (trade 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: Dolores C; Sankyo Co., Ltd.) ... 1 0.5 parts by weight 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 Kalgen EX-70 (trade 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 or more The ingredients 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) Newcalgen EX-70 (trade name) ... 2
0.0 parts by weight (4) Newcalgen 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) Newcalgen EX-70 (trade name) ... 1
5.0 parts by weight (4) Newkalgen 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 In the same manner as in Formulation Example 18, except that Newcalgen SX-C (trade name) was changed to 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 Preparation 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 above, Newcalgen SX-C (trade name) is converted to a condensate of sodium salt of naphthalene sulfonic acid and formalin (trade name: Laberin FAN; manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.). A wettable powder was obtained in the same manner as in Formulation Example 18 except that it 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 the above Formulation Example 18, Nucargen SX-C (trade name) was mixed with an anionic activator (trade name: Dispers).
A hydrating powder was obtained in the same manner as in Preparation Example 18 except that the hydrating agent was changed to ing agent SI;
【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。Preparation Example 29 Preparation Example 18 is the same as Preparation Example 18 except that Newcalgen SX-C (trade name) is changed to sodium salt of oleylmethyl taurate (trade name: Hostapon T; manufactured by Hoechst). 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 Formulation Example 2 (1) Compound A (purity 95%) ... 5.42 parts by weight (2) Ammonium salt of DL-form of compound B (purity 98.
6%) ・ ・ ・ 52.15 parts by weight (3) Newcalgen 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 Formulation 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) Newcalgen EX-70 (trade 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-mentioned formulation examples and comparative formulation examples, and 25 to 30 was 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 compound A, which is a herbicidal active ingredient, was determined by liquid chromatography analysis. The results are shown in Table 1.
【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 Pharmaceutical Products) 1 g of the wettable powder obtained in the above-mentioned formulation examples and comparative formulation examples was placed in a weighing bottle with an internal volume of 30 ml, and the desiccator was kept at a relative humidity of 70%. The sample was placed in a container, weighed at regular intervals, and as a constant weight (maximum moisture absorption) value, the moisture absorption rate obtained from the following equation and the time required to reach the constant weight value were obtained. The results are shown in Table 2.
【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 above.
The results are shown in Table 3.
【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) Roundup (trade name, Monsanto; 41% isopropylamine salt of compound D, 59% water and surfactant etc.) Content: 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 Inc .; 38% of trimethylsulfonium salt of Compound D, water and surfactant) 62% by weight) ... 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) Grass duty (trade name, Sankyo Co., Ltd .; 20% ammonium salt of compound D, inorganic salts, surfactant and Dye etc. are contained 80%) ... 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 pH was measured. The results are shown in Table 4.
【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 (Hygroscopic rate of formulation) In the same manner as in Test Example 2, the moisture absorption rate of the wettable powder obtained in the above formulation example and the time required to reach the constant weight value were determined. The results are shown in Table 5.
【００５６】[0056]
【表５】 [Table 5]
Claims (1)
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-
[(Hydroxy) (methyl) phosphinoyl] butyrylalanylalanine, N- (phosphonomethyl) glycine, and at least one selected from the group consisting of salts thereof as an active ingredient, and an inorganic magnesium salt. An improved herbicidal composition comprising the addition of:
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 |
|---|---|---|---|
| JP36143191 | 1991-12-27 | ||
| JP3-361431 | 1991-12-27 | ||
| JP36199592A JP3253392B2 (en) | 1991-12-27 | 1992-12-25 | Improved herbicidal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05271021A true JPH05271021A (en) | 1993-10-19 |
| JP3253392B2 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) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0764404A1 (en) * | 1995-09-21 | 1997-03-26 | Ishihara Sangyo Kaisha, Ltd. | Granular herbicidal composition |
| WO1998034482A1 (en) * | 1997-02-05 | 1998-08-13 | Basf Aktiengesellschaft | Sulphonylurea and/adjuvant based solid mixtures |
| US6093681A (en) * | 1996-10-25 | 2000-07-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| WO2001080644A1 (en) * | 2000-04-26 | 2001-11-01 | Ishihara Sangyo Kaisha, Ltd. | Solid herbicidal composition |
| JP2002012509A (en) * | 2000-04-26 | 2002-01-15 | Ishihara Sangyo Kaisha Ltd | Solid herbicidal composition |
| WO2001078512A3 (en) * | 2000-04-13 | 2002-03-28 | Fmc Corp | Safening crops from herbicidally active n-phosphonomethyl-glycines |
| WO2003055313A1 (en) * | 2001-12-27 | 2003-07-10 | Sumitomo Chemical Company, Limited | Mixed fine grains containing glyphosate |
| WO2003055312A1 (en) * | 2001-12-27 | 2003-07-10 | Sumitomo Chemical Company, Limited | Fine grains for controlling weeds stable to climate changes |
| US8822443B2 (en) | 2006-03-02 | 2014-09-02 | Ishihara Sangyo Kaisha, Ltd. | Solid herbicidal composition |
-
1992
- 1992-12-25 JP JP36199592A patent/JP3253392B2/en not_active Expired - Lifetime
Cited By (16)
| 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 |
| EP0764404A1 (en) * | 1995-09-21 | 1997-03-26 | Ishihara Sangyo Kaisha, Ltd. | Granular herbicidal composition |
| US6475953B1 (en) | 1996-10-25 | 2002-11-05 | Monsanto Technology Llc | Composition and method for treating plants with exogenous chemicals |
| US6093681A (en) * | 1996-10-25 | 2000-07-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| WO1998034482A1 (en) * | 1997-02-05 | 1998-08-13 | Basf Aktiengesellschaft | Sulphonylurea and/adjuvant based solid mixtures |
| US6559098B1 (en) | 1997-02-05 | 2003-05-06 | Basf Aktiengesellschaft | Sulphonylurea and/adjuvant based solid mixtures |
| WO2001078512A3 (en) * | 2000-04-13 | 2002-03-28 | Fmc Corp | Safening crops from herbicidally active n-phosphonomethyl-glycines |
| WO2001080644A1 (en) * | 2000-04-26 | 2001-11-01 | Ishihara Sangyo Kaisha, Ltd. | Solid herbicidal composition |
| JP2002012509A (en) * | 2000-04-26 | 2002-01-15 | Ishihara Sangyo Kaisha Ltd | Solid herbicidal composition |
| EP1825753A3 (en) * | 2000-04-26 | 2009-01-28 | Ishihara Sangyo Kaisha, Ltd. | Stabilisation of solid herbicidal compositions comprising flazasulfuron |
| JP2011236248A (en) * | 2000-04-26 | 2011-11-24 | Ishihara Sangyo Kaisha Ltd | Solid herbicidal composition |
| WO2003055313A1 (en) * | 2001-12-27 | 2003-07-10 | Sumitomo Chemical Company, Limited | Mixed fine grains containing glyphosate |
| WO2003055312A1 (en) * | 2001-12-27 | 2003-07-10 | Sumitomo Chemical Company, Limited | Fine grains for controlling weeds stable to climate changes |
| AU2002362190B2 (en) * | 2001-12-27 | 2007-07-12 | Sumitomo Chemical Company Limited | Fine grains for controlling weeds stable to climate changes |
| AU2002359946B2 (en) * | 2001-12-27 | 2007-07-12 | Bayer Cropscience | Mixed fine grains containing glyphosate |
| US8822443B2 (en) | 2006-03-02 | 2014-09-02 | Ishihara Sangyo Kaisha, Ltd. | Solid herbicidal composition |
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|---|---|
| JP3253392B2 (en) | 2002-02-04 |
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