JPH0543518A - Haloalkyl phenyl ketone derivative and seed disinfection agent - Google Patents
Haloalkyl phenyl ketone derivative and seed disinfection agentInfo
- Publication number
- JPH0543518A JPH0543518A JP22635791A JP22635791A JPH0543518A JP H0543518 A JPH0543518 A JP H0543518A JP 22635791 A JP22635791 A JP 22635791A JP 22635791 A JP22635791 A JP 22635791A JP H0543518 A JPH0543518 A JP H0543518A
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- present
- seed
- group
- phenyl ketone
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Abstract
(57)【要約】
【目的】 本発明は優れた種子消毒活性を有するハロア
ルキルフェニルケトン誘導体を提供することを目的とす
る。
【構成】 本発明のハロアルキルフェニルケトン誘導体
は一般式（１）で表される。
一般式
【化１】
（式中、Ｒ1は、水素原子、メチル基、フェニル基を示
し、Ｒ2は、シアノ基、ニトロ基を示し、Ｘ1は、水素原
子またはハロゲン原子を示し、Ｘ2は、ハロゲン原子を
示す）(57) [Summary] [Object] An object of the present invention is to provide a haloalkylphenylketone derivative having excellent seed disinfecting activity. [Structure] The haloalkyl phenyl ketone derivative of the present invention is represented by the general formula (1). General formula [Chemical formula 1] (In the formula, R 1 represents a hydrogen atom, a methyl group or a phenyl group, R 2 represents a cyano group or a nitro group, X 1 represents a hydrogen atom or a halogen atom, and X 2 represents a halogen atom. Show)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、新規なハロアルキルフ
ェニルケトン誘導体に関する。さらに詳しくは、後記の
一般式（１）で示されるハロアルキルフェニルケトン誘
導体並びに該誘導体を活性成分として含有する種子消毒
剤に関する。したがって、本発明は、化学工業並びに農
園芸用分野、特に農薬製造業分野で有用である。FIELD OF THE INVENTION The present invention relates to novel haloalkyl phenyl ketone derivatives. More specifically, it relates to a haloalkylphenylketone derivative represented by the following general formula (1) and a seed disinfectant containing the derivative as an active ingredient. Therefore, the present invention is useful in the chemical industry and the fields of agriculture and horticulture, especially in the field of agrochemical manufacturing.
【０００２】[0002]
【従来の技術】これまで、本発明化合物に化学構造上類
似の化合物としてα−クロロ−β−オキソ−ベンゼンプ
ロパンニトリルの合成法が記載されている（ブルテン
ドゥラ ソシエテ シミク フランス １９６９年 第
６２８頁）。しかしながら、本発明の一般式（１）で表
される化合物については知られていない。2. Description of the Related Art So far, a method for synthesizing .alpha.-chloro-.beta.-oxo-benzenepropanenitrile as a compound similar in chemical structure to the compound of the present invention has been described.
Dura Society Cimic France 1969 p.628). However, the compound represented by the general formula (1) of the present invention is not known.
【０００３】[0003]
【発明が解決しようとする課題】稲馬鹿苗病などに対す
る種子消毒剤には、これまで各種薬剤が使用されてきて
いるが、薬剤抵抗性の問題から使用できなくなるか、使
用が制限されてきており必ずしも満足すべき殺菌剤とは
いいがたいものがある。従って、これらの分野では、従
来の薬剤と骨格が異なり、しかも安全性の高い新規な殺
菌剤の出現が要望されている。Although various chemicals have been used as seed disinfectants against rice barley seedling disease and the like, they have become unusable or their use has been restricted due to the problem of drug resistance. Therefore, there are some bactericides that are not always satisfactory. Therefore, in these fields, the emergence of a novel fungicide having a skeleton different from that of conventional drugs and having high safety is demanded.
【０００４】本発明は、これらの要望に合致した新規殺
菌剤を提供せんとすることにある。The present invention seeks to provide a novel fungicide that meets these needs.
【０００５】[0005]
【課題を解決するための手段】本発明者らは上記目的を
達成するために、数多くの化合物を合成し、それらの有
用性について鋭意検討した。その結果、下記の一般式
（１）で表されるハロアルキルフェニルケトン誘導体が
文献未記載の新規化合物であり、病害感染種子、とりわ
け稲馬鹿苗病感染籾に顕著な種子消毒活性と安全性を有
することを見いだした。[Means for Solving the Problems] In order to achieve the above-mentioned object, the present inventors have synthesized a number of compounds and have made extensive studies on their usefulness. As a result, the haloalkyl phenyl ketone derivative represented by the following general formula (1) is a novel compound that has not been described in the literature, and has a remarkable seed disinfecting activity and safety for disease-infected seeds, especially rice scab-infected paddy rice. I found a thing.
【０００６】従って、第１の本発明の要旨とするところ
は、次の一般式（１）Therefore, the gist of the first aspect of the present invention lies in the following general formula (1):
【０００７】[0007]
【化３】 [Chemical 3]
【０００８】（式中、Ｒ1は、水素原子、メチル基、フ
ェニル基を示し、Ｒ2は、シアノ基、ニトロ基を示し、
Ｘ1は、水素原子、またはハロゲン原子を示し、Ｘ2はハ
ロゲン原子を示す）で表されるハロアルキルフェニルケ
トン誘導体である。(Wherein R 1 represents a hydrogen atom, a methyl group or a phenyl group, R 2 represents a cyano group or a nitro group,
X 1 represents a hydrogen atom or a halogen atom, and X 2 represents a halogen atom).
【０００９】第２の本発明の要旨とするところは、上記
一般式（１）のハロアルキルフェニルケトン誘導体を活
性成分として含有することを特徴とする種子消毒剤であ
る。次に、一般式（１）で表される本発明化合物の具体
例を表１に示した。なお、化合物Ｎｏ．は以下の実施例
および試験例でも参照される。A second aspect of the present invention is a seed disinfectant containing the haloalkylphenylketone derivative represented by the general formula (1) as an active ingredient. Next, Table 1 shows specific examples of the compound of the present invention represented by the general formula (1). Compound No. Is also referred to in the following examples and test examples.
【００１０】[0010]
【化４】 [Chemical 4]
【００１１】[0011]
【表１】 [Table 1]
【００１２】[0012]
【作用】本発明の一般式（１）の化合物は、新規化合物
である。そして、式（１）化合物は、種子消毒剤の活性
成分として作用する。The compound of the general formula (1) of the present invention is a novel compound. The compound of formula (1) then acts as the active ingredient of the seed disinfectant.
【００１３】[0013]
本発明化合物の製造方法 本発明の一般式（１）の化合物は、次に説明する方法に
より製造される。一般式（１）で示されるフェニルケト
ン誘導体を溶媒中で適当なハロゲン化剤と反応させるこ
とにより製造できる。Method for Producing Compound of the Present Invention The compound of the general formula (1) of the present invention is produced by the method described below. It can be produced by reacting the phenyl ketone derivative represented by the general formula (1) with a suitable halogenating agent in a solvent.
【００１４】[0014]
【化５】 （式中、Ｒ1、Ｒ2、Ｘ1、Ｘ2、は前記と同じ意義を有す
る）[Chemical 5] (In the formula, R 1 , R 2 , X 1 , and X 2 have the same meanings as described above.)
【００１５】この反応に使用するハロゲン化剤として
は、塩素、臭素、ヨウ素、塩化スルフリル、臭化第二
銅、三臭化ピロリドンなどである。The halogenating agent used in this reaction includes chlorine, bromine, iodine, sulfuryl chloride, cupric bromide, pyrrolidone tribromide and the like.
【００１６】溶媒としては、ジクロロメタン、クロロホ
ルム、四塩化炭素などのハロゲン化炭化水素類、メタノ
ール、エタノールなどのアルコール類、酢酸エチルなど
のエステル類、酢酸、ジオキサンおよび水とこれらの混
合溶媒が使用できる。As the solvent, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, alcohols such as methanol and ethanol, esters such as ethyl acetate, acetic acid, dioxane and water and mixed solvents thereof can be used. ..
【００１７】反応温度は、０℃から溶媒の沸点までの範
囲が使用できるが、通常、０℃から室温の範囲で行う。The reaction temperature may be in the range of 0 ° C. to the boiling point of the solvent, but it is usually in the range of 0 ° C. to room temperature.
【００１８】反応終了後は、水とトルエン、クロロホル
ムなどの有機溶媒を加えて目的物を分取し、溶媒を留去
することにより本発明化合物を得ることができる。After completion of the reaction, the compound of the present invention can be obtained by adding water and an organic solvent such as toluene or chloroform to fractionate the desired product and distill off the solvent.
【００１９】この方法による製造例を実施例１〜２に示
した。なお、出発原料である（２）式化合物は新規化合
物であるが、公知の方法により容易に合成できる。Examples of production by this method are shown in Examples 1 and 2. The compound of formula (2), which is a starting material, is a novel compound, but can be easily synthesized by a known method.
【００２０】実施例１ ２−ブロモ−１−（２−メトキ
シ−４−メチルフェニル）−２−ニトロエタノン（化合
物Ｎｏ．４）の製造 撹拌機を取り付けた１００ｍｌ容量の四つ口フラスコに
１−（２−メトキシ−４−メチルフェニル）−２−ニト
ロエタノン４．２ｇ、酢酸６０ｍｌを入れ、この混合物
に臭素３．２ｇを１０℃にて滴下し、同温度で３０分間
撹拌した。反応終了後、水を加えてクロロホルムにて抽
出し、有機層を水洗後、無水硫酸ナトリウムにて乾燥し
た。減圧下で溶媒を留去すると、標記化合物が褐色の粗
結晶として２．７ｇ得られた。トルエン、ｎ−ヘキサン
混合溶媒にて再結晶すると、無色の結晶となり、融点９
２．５〜９４．５℃を示した。Example 1 Preparation of 2-bromo-1- (2-methoxy-4-methylphenyl) -2-nitroethanone (Compound No. 4) 1- (in a 100 ml four-necked flask equipped with a stirrer. 4.2 g of 2-methoxy-4-methylphenyl) -2-nitroethanone and 60 ml of acetic acid were added, 3.2 g of bromine was added dropwise to this mixture at 10 ° C., and the mixture was stirred at the same temperature for 30 minutes. After the reaction was completed, water was added and the mixture was extracted with chloroform. The organic layer was washed with water and dried over anhydrous sodium sulfate. When the solvent was distilled off under reduced pressure, 2.7 g of the title compound was obtained as brown crude crystals. Recrystallization from a mixed solvent of toluene and n-hexane gives colorless crystals with a melting point of 9
The temperature was 2.5 to 94.5 ° C.
【００２１】実施例２ ２−ブロモ−２−フェニル−１
−（２−メトキシ−４−メチルフェニル）−３−オキソ
プロパンニトリル（化合物Ｎｏ．８）の製造 撹拌機を取り付けた２００ｍｌ容量の四つ口フラスコに
２−フェニル−１−（２−メトキシ−４−メチルフェニ
ル）−３−オキソプロパンニトリル４ｇ、酢酸６０ｍ
ｌ、クロロホルム６０ｍｌを入れ、この混合物に臭素
２．４ｇを室温にて滴下し、室温で２時間撹拌した。反
応終了後、水を加えてクロロホルムにて抽出し、有機層
を水洗後、無水硫酸ナトリウムにて乾燥した。減圧下で
溶媒を留去すると、標記化合物が褐色の粗結晶として
４．８ｇ得られた。トルエン、ｎ−ヘキサン混合溶媒に
て再結晶すると、無色の結晶となり、融点１１０〜１１
１℃を示した。Example 2 2-Bromo-2-phenyl-1
Production of-(2-methoxy-4-methylphenyl) -3-oxopropanenitrile (Compound No. 8) 2-phenyl-1- (2-methoxy-4) was added to a 200 ml four-necked flask equipped with a stirrer. -Methylphenyl) -3-oxopropanenitrile 4 g, acetic acid 60 m
1, 60 ml of chloroform were added, 2.4 g of bromine was added dropwise to this mixture at room temperature, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, water was added and the mixture was extracted with chloroform. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 4.8 g of the title compound as brown crude crystals. When recrystallized with a mixed solvent of toluene and n-hexane, colorless crystals are obtained with a melting point of 110-11.
It showed 1 ° C.
【００２２】実施例 本発明の種子消毒剤の製剤化方法 本発明に係わる種子消毒剤として使用する場合は、水和
剤、乳剤、水和顆粒剤、フロアブルなどの一般に慣用さ
れる形態に製剤化して使用できる。使用される担体は固
体または液体のいずれでもよく、また特定の担体に限定
されるものではない。固体担体としては、たとえば、種
々の粘土類、カオリン、クレー、けいそう土、タルク、
シリカなどが挙げられる。Example Method for Formulating a Seed Disinfectant of the Present Invention When used as a seed disinfectant according to the present invention, it is formulated into a generally used form such as a wettable powder, an emulsion, a hydrated granule, and a flowable powder. Can be used. The carrier used may be either solid or liquid and is not limited to a particular carrier. Examples of the solid carrier include various clays, kaolin, clay, diatomaceous earth, talc,
Examples thereof include silica.
【００２３】液体担体としては、本発明に係る活性成分
化合物に対して溶媒となるものおよび非溶媒であっても
補助剤により活性成分化合物を分散または溶解されうる
ものならば、使用できる。例えば、ベンゼン、キシレ
ン、トルエン、ケロシン、アルコール類、ケトン類、ジ
メチルスルホキシド、ジメチルホルムアミドなどが使用
できる。これに、適当な界面活性剤およびその他の補助
剤、たとえば、展着剤、固着剤などを混合し、水和剤、
乳剤、水和顆粒剤あるいはフロアブル剤として使用でき
る。本発明の種子消毒剤中の含有量は、製剤全量の１０
〜１５％部（重量％）が適当である。また、本発明の化
合物は省力化および防除効果を確実にするために、他の
種子消毒剤と混合して使用することができる。As the liquid carrier, those which serve as a solvent for the active ingredient compound of the present invention and nonsolvents can be used so long as they can disperse or dissolve the active ingredient compound with an auxiliary agent. For example, benzene, xylene, toluene, kerosene, alcohols, ketones, dimethylsulfoxide, dimethylformamide and the like can be used. To this, a suitable surfactant and other auxiliary agents such as a spreading agent and a fixing agent are mixed, and a wettable powder,
It can be used as an emulsion, hydrated granule or flowable. The content of the seed disinfectant of the present invention is 10% of the total amount of the preparation.
-15% by weight (wt%) is suitable. In addition, the compound of the present invention can be used as a mixture with other seed disinfectants in order to save labor and ensure control effects.
【００２４】次に本発明に係わる化合物を種子消毒剤と
して製剤化する方法について実施例３〜４を示すが、本
発明は以下の実施例に限定されるものではない。Next, Examples 3 to 4 will be shown for a method of formulating the compound according to the present invention as a seed disinfectant, but the present invention is not limited to the following Examples.
【００２５】実施例３ （水和剤） 化合物Ｎｏ．１の化合物 ３０部、ホワイトカーボン
１５部、ポリオキシエチレンアルキルアリールエーテル
３部、リグニンスルホン酸ナトリウム ２部およびク
レー ５０部を混合し、十分粉砕して、活性成分３０％
を含有する水和剤を得る。Example 3 (Wettable powder) Compound No. 1 part 30 parts, white carbon
15 parts, 3 parts of polyoxyethylene alkylaryl ether, 2 parts of sodium lignin sulfonate and 50 parts of clay are mixed and sufficiently ground to give 30% of active ingredient.
A wettable powder containing is obtained.
【００２６】実施例４ （乳剤） 化合物Ｎｏ．７の化合物 ２０部、ポリオキシエチレン
ノニルフェニルエーテル１０部、キシレン ７０部を混
合して溶解すれば、活性成分２０％を含有する乳剤を得
る。Example 4 (Emulsion) Compound No. 20 parts of the compound of Example 7, 10 parts of polyoxyethylene nonylphenyl ether and 70 parts of xylene are mixed and dissolved to obtain an emulsion containing 20% of the active ingredient.
【００２７】上記実施例３〜４の水和剤、乳剤を水で１
０〜１０００倍に希釈して種籾重量の１〜２倍容量液中
に種籾を１０分間〜４８時間浸漬するか、水和剤の場合
は、種籾の０．１〜１．０％重量相当を種籾によく粉衣
することにより、稲馬鹿苗病、稲ごま葉枯病をはじめと
する種子伝染性病害を防除することができる。The wettable powder and emulsion of Examples 3 to 4 above were mixed with water to form 1 part.
Dilute the seed pad to 0 to 1000 times and soak the seed pad in a liquid of 1 to 2 times the weight of the seed pad for 10 minutes to 48 hours, or, in the case of a wettable powder, add 0.1 to 1.0% by weight of the seed pad. By well dressing the seed paddy, it is possible to control seed-borne diseases such as inoculum seedling disease and rice sesame leaf blight.
【００２８】[0028]
【発明の効果】次に、本発明化合物の種子消毒剤として
の作用効果を試験例により説明する。The action and effect of the compound of the present invention as a seed disinfectant will be described below with reference to test examples.
【００２９】[0029]
試験例１ 稲馬鹿苗病種子消毒効果試験 蒸気滅菌した稲ワラ培地で培養したベノミル耐性稲馬鹿
苗病菌および感受性稲馬鹿苗病菌（ギベレラ フジクロ
イ Ｇｉｂｂｅｒｅｌｌａ ｆｕｊｉｋｕｒｏｉ）を胞
子懸濁液とし、開花期の稲（品種 日本晴）に各々２回
にわたって噴霧接種し、稲馬鹿苗病菌感染籾（耐性菌感
染籾と感受性菌感染籾の２種類）を得た。Test Example 1 Test for disinfecting seeds of rice bran seedling disease Seeds of flowering stage using spore suspension of benomyl-resistant strain of rice bran disease and susceptible rice bran plant ( Gibberella fujikuroi ) cultivated in steam-sterilized rice straw medium. The cultivar Nihonbare) was spray-inoculated twice each to obtain rice paddy-rice seedlings-infected paddy rice (two types of paddy rice infected with resistant bacterium and paddy infected with susceptible bacterium).
【００３０】上記方法で得た稲馬鹿苗病感染籾を実施例
１の水和剤に準じて調製した各薬剤の所定濃度希釈液中
に種籾対薬剤比（ｖ／ｖ）を１対１の割合で２０℃で２
４時間浸漬した。その後、３０℃で２４時間催芽させ、
鳩胸状になった種籾を慣用の箱育苗法に準じてクミアイ
粒状培土〔呉羽化学工業（株）製〕に播種した。その後
は、ガラス温室内で栽培管理した。Rice bran disease infected rice obtained by the above-mentioned method was prepared according to the wettable powder of Example 1 and diluted with a predetermined concentration of each drug to give a seed rice to drug ratio (v / v) of 1: 1. 2 at 20 ° C
It was immersed for 4 hours. Then, germinate at 30 ° C for 24 hours,
The dove chest-shaped rice seeds were sown on Kumiai granular soil (Kureha Chemical Industry Co., Ltd.) according to a conventional box raising method. After that, cultivation was managed in a glass greenhouse.
【００３１】発病調査は、播種３０日後に、徒長、枯死
などの馬鹿苗病症状を示した発病苗数と健全苗数を調査
（１区当りの調査苗数は約２００本）し、発病苗率
（％）を求めた。これより次式で示したように、無処理
区の発病苗率との対比で種子消毒率（％）を算出した。
また、薬害については、出芽率、生育程度などについて
観察し、下記の薬害指数で表示した。30 days after sowing, the number of diseased seedlings and the number of healthy seedlings showing stupid seedling disease such as maternity and death were investigated 30 days after sowing (the number of seedlings investigated per ward was about 200). The rate (%) was calculated. From this, as shown by the following equation, the seed disinfection rate (%) was calculated in comparison with the diseased seedling rate in the untreated plot.
Regarding the phytotoxicity, the germination rate, the degree of growth, etc. were observed and the following phytotoxicity index was used.
【００３２】[0032]
【数１】 [Equation 1]
【００３３】[0033]
【数２】 [Equation 2]
【００３４】薬害指数 ０＝薬害なし １＝少 ２＝中 ３＝多 ４＝
甚Drug damage index 0 = no drug damage 1 = small 2 = medium 3 = large 4 =
Jin
【００３５】その結果は、表２のとおりである。The results are shown in Table 2.
【００３６】[0036]
【表２】 [Table 2]
【００３７】注１）比較剤１Note 1) Comparative agent 1
【００３８】[0038]
【化６】 （ブルテン ドゥ ラ ソシエテ シミク フランス１
９６９年、第６２８頁に記載の化合物） 注２）市販殺菌剤のベンレート（一般名：ベノミル）を
示す。 注３）（ ）内の数値は無処理区の発病苗率（％）を示
す。[Chemical 6] (Burten de la Societe Simique France 1
969, compound described on page 628) Note 2) Indicates a commercially available fungicide, Benlate (generic name: benomyl). Note 3) The figures in parentheses indicate the diseased seedling rate (%) in untreated plots.
【００３９】試験例２ 稲ごま葉枯病種子消毒効果試験 稲ごま葉枯病多発圃場で自然感染したごま葉枯病菌（コ
クリオボルス ミアベアヌス Ｃｏｃｈｌｉｏｂｏｌｕ
ｓ ｍｉｙａｂｅａｎｕｓ）感染籾（品種 黄金晴）を
採集して、供試籾とした。Test Example 2 Rice sesame leaf blight seed disinfection effect test Sesame leaf blight fungus ( Cochliobolus Myochianus Cochliobolu) naturally infected in a field where rice sesame leaf blight frequently occurs
s. miyabeanus ) -infected paddy (variety: Golden Hare) was collected and used as a test paddy.
【００４０】種子消毒法およびその他操作手順は、試験
例１の稲馬鹿苗病種子消毒効果試験と同様に行った。The seed disinfection method and other operating procedures were the same as those of the test for disinfecting the seeds of the horse mackerel disease in Test Example 1.
【００４１】発病調査は、播種２０日後に稲ごま葉枯病
発病苗数を調査し、試験例１と同様に発病苗率（％）を
求め、これより種子消毒率（％）を算出した。また薬害
についても試験例１と同一の基準で調査した。For the disease onset, the number of rice sesame leaf blight diseased seedlings was examined 20 days after sowing, and the diseased seedling rate (%) was determined in the same manner as in Test Example 1, and the seed disinfection rate (%) was calculated from this. In addition, the same criteria as in Test Example 1 were investigated for chemical damage.
【００４２】その結果は、表３のとおりである。The results are shown in Table 3.
【００４３】[0043]
【表３】 [Table 3]
【００４４】注１） 試験例１の比較剤１と同一化合物
である。 注２） 市販殺菌剤のロブラール（一般名 イソプロジ
オン）３−（３，５−ジクロロフェニル）−Ｎ−２，４
−ジオキソイミダゾリジン−１−カルボキシアミドを示
す。Note 1) The same compound as Comparative Agent 1 of Test Example 1. Note 2) Lobral (generic name: isoprodione) 3- (3,5-dichlorophenyl) -N-2,4, a commercially available fungicide
-Dioxoimidazolidine-1-carboxamide.
フロントページの続き (72)発明者 梶川 和男 神奈川県厚木市戸田2385番地 北興化学寮Front page continuation (72) Inventor Kazuo Kajikawa 2385 Toda, Atsugi City, Kanagawa Prefecture
Claims (2)
し、Ｒ2は、シアノ基、ニトロ基を示し、Ｘ1は、水素原
子またはハロゲン原子を示し、Ｘ2は、ハロゲン原子を
示す）で表されるハロアルキルフェニルケトン誘導体。1. A general formula: (In the formula, R 1 represents a hydrogen atom, a methyl group or a phenyl group, R 2 represents a cyano group or a nitro group, X 1 represents a hydrogen atom or a halogen atom, and X 2 represents a halogen atom. The haloalkyl phenyl ketone derivative represented by these.
し、Ｒ2は、シアノ基、ニトロ基を示し、Ｘ1は、水素原
子またはハロゲン原子を示し、Ｘ2は、ハロゲン原子を
示す）で表されるハロアルキルフェニルケトン誘導体を
活性成分として含有することを特徴とする種子消毒剤。2. A general formula: (In the formula, R 1 represents a hydrogen atom, a methyl group or a phenyl group, R 2 represents a cyano group or a nitro group, X 1 represents a hydrogen atom or a halogen atom, and X 2 represents a halogen atom. The seed disinfectant characterized by containing the haloalkyl phenyl ketone derivative represented by these as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22635791A JPH0543518A (en) | 1991-08-13 | 1991-08-13 | Haloalkyl phenyl ketone derivative and seed disinfection agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22635791A JPH0543518A (en) | 1991-08-13 | 1991-08-13 | Haloalkyl phenyl ketone derivative and seed disinfection agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0543518A true JPH0543518A (en) | 1993-02-23 |
Family
ID=16843888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22635791A Pending JPH0543518A (en) | 1991-08-13 | 1991-08-13 | Haloalkyl phenyl ketone derivative and seed disinfection agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0543518A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001035955A1 (en) * | 1999-11-16 | 2001-05-25 | Toray Industries, Inc. | Benzene derivatives and use thereof as drugs |
| US6899886B2 (en) | 2000-08-11 | 2005-05-31 | Otsuka Chemical Co., Ltd. | Acylacetonitriles, process for preparation thereof and miticides containing the same |
-
1991
- 1991-08-13 JP JP22635791A patent/JPH0543518A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001035955A1 (en) * | 1999-11-16 | 2001-05-25 | Toray Industries, Inc. | Benzene derivatives and use thereof as drugs |
| US6899886B2 (en) | 2000-08-11 | 2005-05-31 | Otsuka Chemical Co., Ltd. | Acylacetonitriles, process for preparation thereof and miticides containing the same |
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