JPS60172946A - Fluorine-containing benzophenone derivative and its use - Google Patents
Fluorine-containing benzophenone derivative and its useInfo
- Publication number
- JPS60172946A JPS60172946A JP2943584A JP2943584A JPS60172946A JP S60172946 A JPS60172946 A JP S60172946A JP 2943584 A JP2943584 A JP 2943584A JP 2943584 A JP2943584 A JP 2943584A JP S60172946 A JPS60172946 A JP S60172946A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- lower alkyl
- alkyl group
- nitro
- group
- 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.)
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Links
Abstract
Description
【発明の詳細な説明】
本発明は、含フツ素ベンゾフェノン誘導体に関し、更に
詳しくは除草活性物質として有用でありトリフルオロメ
チル基およびニトロ基を有する新規ベンゾフェノン誘導
体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to fluorine-containing benzophenone derivatives, and more particularly to novel benzophenone derivatives that are useful as herbicidal active substances and have a trifluoromethyl group and a nitro group.
除草活性を有するベンゾフェノン類は、例えば特公昭５
１−５４４６号公報、特開昭５５−２０７０７号公報、
特開昭５６−１０８７３２号公報に開示されているが、
いずれも構造中にトリフルオロメチル基を含んでいない
。米国特許第３，９５０．８７５号および特開昭５４−
２３２３号公報に、トリフルオロメチル基を含むベンゾ
フェノン誘導体が開示されている。しかし、米国特許第
３．９５０．８７５号では、トリフルオロメチル基を有
さない方のベンゼン環は２置換である。特開昭５４−２
３２３号公報では、トリフルオロメチル基を有さない万
のベンゼン環はアルキル基、ハロゲン化アルキル基、シ
クロアルキル基、ハロゲンまたはアルケニル基のいずれ
か一つとニトロ基とを同時に含んでいない。また、これ
らの公仰ベンゾフェノン類の除草活性は比較的低く、実
用性において十分に満足できるものではなかった。Benzophenones having herbicidal activity are, for example,
1-5446, JP-A-55-20707,
Although disclosed in Japanese Patent Application Laid-Open No. 56-108732,
None of them contain a trifluoromethyl group in their structure. U.S. Patent No. 3,950.875 and Japanese Unexamined Patent Publication No. 1987-
No. 2323 discloses benzophenone derivatives containing a trifluoromethyl group. However, in US Pat. No. 3,950,875, the benzene ring that does not have a trifluoromethyl group is disubstituted. JP-A-54-2
No. 323 discloses that a benzene ring having no trifluoromethyl group does not simultaneously contain any one of an alkyl group, a halogenated alkyl group, a cycloalkyl group, a halogen, or an alkenyl group, and a nitro group. In addition, the herbicidal activity of these benzophenones is relatively low and is not fully satisfactory in terms of practical use.
本発明者らは、ベンゾフェノンの一万のベンゼン環にト
リフルオロメチル基を有する一連の化合物について鋭意
研究を重ねた結果、ある種の新規含フツ素ベンゾフェノ
ン化合物は除草活性に優れ、就中、水田の単子葉雑草お
よび双子葉雑草に対し強力かつ広い殺草スペクトラムを
持ち、例えばミズ力ヤッリ、ホタルイ、ウリカワ等の難
防除雑草の防除に低濃度で卓効を示すが、イネに対して
薬害を実質的に与えないという優れた効果を見い出し、
本発明を完成するに至った。The present inventors have conducted intensive research on a series of benzophenone compounds having trifluoromethyl groups in the 10,000 benzene rings. As a result, certain new fluorine-containing benzophenone compounds have excellent herbicidal activity, especially in rice fields. It has a powerful and wide-spectrum herbicidal spectrum against monocotyledonous and dicotyledonous weeds, and is highly effective at low concentrations for controlling difficult-to-control weeds such as Mizurikiyari, Hotarui, and Urikawa, but it does not cause chemical damage to rice. We discovered the excellent effect of virtually no effect on
The present invention has now been completed.
すなわち、本発明の要旨は、
〔式中、Ｒは直鎖もしくは分校のアルキル基、ハロケン
化アルキル基、シクロアルキル基、ハロゲンまたはアル
ケニル基を、Ｍは水素、アルカリは同一または異なって
、水素または低級アルキル基である。〕または−ＳＯ−
Ｒ（ここで１３３は低級アルキル基あるいは置換または
非置換フェニル基である。）を表わす。］
で示される含フッ素ベンゾフェノンＭ導体、表；よび含
フツ素ベンゾフェノン誘導（Ｉｌの一種または二種以ト
を成分として含有することを特徴とする除草組成物に存
する。That is, the gist of the present invention is [wherein R is a linear or branched alkyl group, a halokenated alkyl group, a cycloalkyl group, a halogen or an alkenyl group, M is hydrogen, and the alkalis are the same or different and represent hydrogen or It is a lower alkyl group. ] or -SO-
R (herein, 133 is a lower alkyl group or a substituted or unsubstituted phenyl group). ] A fluorine-containing benzophenone M conductor shown in Table;
Ｏ１ｊ記公知のベンゾフェノン類に比較して、本発明化
合物の化学構造の特徴は、
（１１一方のベンゼン環に１個のトリフルオロメチル基
を督している点、および
（２１他方のベンゼン環の５位にニトロ基、４位に前記
置換基ＯＭおよび３位に前記置換基Ｒを有している点、
にあり、これらの化学構造上の特徴が本発明化合物の除
草剤、特に水田用除草剤としての優秀性に寄与している
ものと考えられる。Compared to the known benzophenones described in O1j, the chemical structure of the compound of the present invention is characterized by (11) that one benzene ring has one trifluoromethyl group, and (21) that the other benzene ring has one trifluoromethyl group. It has a nitro group at the 5th position, the substituent OM at the 4th position, and the substituent R at the 3rd position, and these chemical structural features make the compound of the present invention a herbicide, especially a herbicide for paddy fields. This is thought to contribute to its superiority as an agent.
本発明化合物の具体例を融点すたは屈折亭ｎＤと共に示
せば次の通りである： −
（１１４−ヒドロキシ−３−メチル−５−ニトロ−２−
トリフルオロメチルベンゾフェノン（ｍｐ１０４〜１０
５”Ｃ〕
（２）３−エチル−４−ヒドロキシ−５−ニトロ−２−
トリフルオロメチルベンゾフェノン（ｍｐ７３〜７４”
Ｃ）
（３）４−ヒドロキシ−５−ニトロ−３−プロピル−２
−トリフルオロメチルベンゾフェノン（ｍｐ４５〜４６
”Ｃ〕
（４）４−ヒドロキシ−５−ニトロ−３−イソプロピル
−２−トリフルオロメチルベンゾフェノン（ｍ２４９〜
５０°Ｃ）
ｆ５＋３−フクロヘキシル−４−ヒ）’ロキソー５−二
トロー２−トリフルオロメチルベンゾフェノン（６）３
−アリル−４−ヒドロキシ−５−ニトロ−２−トリフル
オロメチルベンゾフェノン（ｒｎｐ ６３”Ｃ）（７）
４−ヒドロキシ−５−ニトロ−３，２−ジトリフルオロ
メチルベンゾフェノン
１１７゛Ｃ）
（８）４−ヒドロキソ−３−メチル−５−ニトロ−２−
トリフルオロメチルベンゾフェノン・ナトリウム塩（
ｍｐ ｌ ９ ４”Ｃ）
（９）４−アセトキシ−３−メチル−５−二トロ＝２→
トリフルオロメチルベンゾフェノン（ｍｐ１１８″Ｃ〕
（１０） ４−プチロイルオキシー３−メチル−５−ニ
トロ−２−トリフルオロメチルベンゾフェノン（０
１１，５３２６）
（１１）３−メチル−５−二トロー４−（Ｎ、Ｎ−ジメ
チルカルバモイルオキシ）−２−１−リメチルベンゾフ
エノン（ｍｐ １０８〜１１０°Ｃ）（功３−メチルー
５−二トロー４−パラトルエンスルホニルオキシー２−
トリフルオロメチルベン（１３） ４−メトキン−３−
メチル−５−ニトロ−２−トリフルオロメチルベンゾフ
ェノン（ｍｐ６８〜６９”Ｃ）
（１４）４−７！Ｉルオキシ−３−メチル−５−二トロ
ア５〜７６°Ｃ）
（１５） ４−ヒドロキシ−３−メチル−５−ニトロ−
３−トリフルオロメチルベンゾフェノン（ｍｐ１３９〜
１４１’ｃ）
（１６） ４−ヒドロキシ−３−メチル−５−二トロー
４−トリフルオロメチルベンゾフェノン（ｍｐ−１１２
〜１１３°Ｃ）
（１７Ｊ ３−フルオロ−４−ヒドロキシ−５−ニトロ
−２−トリフルオロメチルベンゾフェノン（ｍｐ１１４
〜１１６”Ｃ）
Ｍが水素である本発明のベンゾフェノン誘導体〔式中、
Ｘはヒドロキシ基または塩素を表わす。〕
で示されるトリフルオロメチル安息香酸またはその酸ク
ロリドと式：
〔式中、ｋは前記と同意義、Ｍは低級アルキル基を表わ
す。〕
で示される置換フェノール誘導体を、ポリリン酸または
塩化第二鉄を用いるフリーゾルタラフッ反応に付して調
製した式：
〔式中、ＫおよびＭは（ｌｌｌｌと同意義。）で示され
る化合物を氷冷上硝酸／硫酸でニトロ化してから５０〜
１００”Ｃでヨウ化水素酸により脱アルキル化するか、
あるいはまず脱アルキル化してからニトロ化することに
よって調製できる。Specific examples of the compounds of the present invention, together with their melting points and refractories, are as follows: - (114-hydroxy-3-methyl-5-nitro-2-
Trifluoromethylbenzophenone (mp104-10
5”C] (2) 3-ethyl-4-hydroxy-5-nitro-2-
Trifluoromethylbenzophenone (mp73-74”
C) (3) 4-hydroxy-5-nitro-3-propyl-2
-Trifluoromethylbenzophenone (mp45-46
"C" (4) 4-hydroxy-5-nitro-3-isopropyl-2-trifluoromethylbenzophenone (m249~
50°C)
-Allyl-4-hydroxy-5-nitro-2-trifluoromethylbenzophenone (rnp 63”C) (7)
4-Hydroxy-5-nitro-3,2-ditrifluoromethylbenzophenone 117゛C) (8) 4-Hydroxo-3-methyl-5-nitro-2-
Trifluoromethylbenzophenone sodium salt (
mp l 9 4”C) (9) 4-acetoxy-3-methyl-5-nitro=2→
Trifluoromethylbenzophenone (mp118″C) (10) 4-butyroyloxy-3-methyl-5-nitro-2-trifluoromethylbenzophenone (0 11,5326) (11) 3-methyl-5-nitro-4- (N,N-dimethylcarbamoyloxy)-2-1-limethylbenzophenone (mp 108-110°C) (3-methyl-5-nitro-4-para-toluenesulfonyloxy-2-
Trifluoromethylben (13) 4-methquin-3-
Methyl-5-nitro-2-trifluoromethylbenzophenone (mp68-69"C) (14) 4-7!Iruoxy-3-methyl-5-nitroa5-76°C) (15) 4-Hydroxy- 3-methyl-5-nitro-
3-Trifluoromethylbenzophenone (mp139~
141'c) (16) 4-hydroxy-3-methyl-5-nitro-4-trifluoromethylbenzophenone (mp-112
~113°C) (17J 3-fluoro-4-hydroxy-5-nitro-2-trifluoromethylbenzophenone (mp114
~116"C) Benzophenone derivatives of the present invention in which M is hydrogen [wherein,
X represents a hydroxy group or chlorine. ] Trifluoromethylbenzoic acid or its acid chloride represented by the formula: [In the formula, k has the same meaning as above, and M represents a lower alkyl group. ] A substituted phenol derivative represented by the following formula was prepared by subjecting it to a free-solat fluoride reaction using polyphosphoric acid or ferric chloride: [wherein K and M are the same as (llll)] is nitrated with nitric acid/sulfuric acid on ice, and then 50~
dealkylation with hydroiodic acid at 100"C, or
Alternatively, it can be prepared by first dealkylating and then nitrating.
Ｍが低級アルキル基である本発明のベンゾフェノン誘導
体ｆＩ］は、上記製法の最後の脱アルキル化を省くこと
により調製できる。The benzophenone derivative fI of the present invention in which M is a lower alkyl group can be prepared by omitting the final dealkylation in the above-mentioned process.
Ｍがアルカリ金属である本発明のベンゾフェノン誘導体
ｆｉｌは、Ｍが水素である誘導一体（Ｉｌにアルカリ金
属の塩基を加えることによって容易に調製でここでＲ３
は前記と同意義。〕である本発明のベンゾフェノン誘導
体ｆｌｌは、Ｍが水素である誘導体（Ｉｌに該基の酸ク
ロリドまたは酸蕪水物を反応させることより調製できる
。The benzophenone derivative fil of the present invention, in which M is an alkali metal, can be easily prepared by adding an alkali metal base to the derivative monomer (Il, in which M is hydrogen), where R3
has the same meaning as above. ] The benzophenone derivative fl1 of the present invention, in which M is hydrogen, can be prepared by reacting a derivative (I1) in which M is hydrogen with an acid chloride or an acid hydrate of the group.
Ｍが低級アルケニル基である本発明のベンゾフェノン誘
導体ｆｉｌは、Ｍが水素である誘導体［１１をアルカリ
の存在下低級アルケニルハライドと反応させることによ
り調製できる。The benzophenone derivative fil of the present invention in which M is a lower alkenyl group can be prepared by reacting the derivative [11] in which M is hydrogen with a lower alkenyl halide in the presence of an alkali.
またｋがアルケニル基、例えばアリル基でありＭが水素
である本発明のベンゾフェノン誘導体は）〔式中、Ｍは
水素を表わす。〕
で示される化合物にＣＨ＝ｃＨ７ＣＨ２−Ｙ （ここで
Ｙは臭素または塩素である。）を常法によりアリル化し
て生成するＭ′がアリル基である化合物（Ｖｌを次いで
常法によりアリル転位することによって調製できる。Further, the benzophenone derivative of the present invention in which k is an alkenyl group, for example, an allyl group and M is hydrogen, is (wherein, M represents hydrogen). ] A compound in which M' is an allyl group (Vl is then allyl rearranged by a conventional method), which is produced by allylating the compound represented by CH=cCH7CH2-Y (where Y is bromine or chlorine) by a conventional method. It can be prepared by
本発明のベンゾフェノン誘導体［１１は、前記除草剤と
して有用である他、植物生長調節剤、殺菌剤、抗炎症剤
などの医農薬、またはこれらの合成中間体として利用す
ることができる。The benzophenone derivative [11] of the present invention is useful as the above-mentioned herbicide, and can also be used as a plant growth regulator, a fungicide, a medicinal or agrochemical agent such as an anti-inflammatory agent, or a synthetic intermediate thereof.
除草剤として使用する場合、そのま＼で、あるいは適当
な担体と混合して乳剤、水和剤、粒剤などの剤形として
用いればよい。When used as a herbicide, it may be used as it is or mixed with a suitable carrier to form a dosage form such as an emulsion, a wettable powder, or a granule.
除草剤に調製する場合、適当な担体としては、固型担体
である粘土、カオリン、タルク、硅藻土、シリカ、炭酸
カルシウムなど、液体担体であるベンゼン、アルコール
、アセトン、キシレン、メチルフタリン、ンクロヘキサ
ノン、ジメチルホルムアミド、ジメチルスルホキシド、
動植物油、脂肪酸とそのエステルおよび各種界面活性剤
を例示することができる。When preparing herbicides, suitable carriers include solid carriers such as clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, etc., and liquid carriers such as benzene, alcohol, acetone, xylene, methylphthalin, and nclohexanone. , dimethylformamide, dimethyl sulfoxide,
Examples include animal and vegetable oils, fatty acids and their esters, and various surfactants.
さらに、除草剤に通常使用される一助剤、たとえば展着
剤、乳化剤、湿潤剤、固着剤などを適宜加えることがで
きる。Furthermore, auxiliary agents commonly used in herbicides, such as spreading agents, emulsifiers, wetting agents, and fixing agents, can be added as appropriate.
本発明のベンゾフェノン銹導体山を含む除草剤組成物に
は、他の農業用殺菌剤、殺虫剤、殺線虫剤、除草剤、植
物生長調節剤、土壌改良剤、肥料などを配合することが
できる。Other agricultural fungicides, insecticides, nematicides, herbicides, plant growth regulators, soil conditioners, fertilizers, etc. may be added to the herbicide composition containing the benzophenone conductor of the present invention. can.
次に実施例および試験例を示して本発明を具体的に説明
する。Next, the present invention will be specifically explained with reference to Examples and Test Examples.
実施例１
４−ヒドロキシ−３−メチル−５−ニトロ−２−トリフ
ルオロメチルベンゾフェノン（化合物（１＋）の製造ニ
ー
塩化第二鉄３．Ｏｇ（１８ミリモル）に０−トリフルオ
ロメチルベンゾイルクロリド３．６ｇ（ｘ７ミリモル〕
を加えた混合液に氷冷下０−メチルアニソール２．１ｇ
（１８ミリモル〕を滴下した後、５°Ｃで１時間、２０
”Ｃで２時間攪拌した。反応混合物を氷水中に注ぎ、ク
ロロホルム抽出した。荷′機層を１０％塩酸、飽和食塩
水で洗浄して硫酸ナトリウムで乾燥した後、溶媒留去し
て得た粗結晶を５５％ヨウ化水素酸５０ｔｒｔｌに懸濁
し、１０時時間中かに還流した。反応液を冷却し、生じ
た結晶をρ集して水洗した。この結晶を酢酸エチルに溶
去した。得られた粗結晶を濃硫酸５ｍｌに溶解し氷冷上
濃硝酸１．２ ｔｒｔｌを滴下後、３時間水冷下撹拌し
た。反応液を氷水に注ぎクロロホルム抽出した。Example 1 Preparation of 4-hydroxy-3-methyl-5-nitro-2-trifluoromethylbenzophenone (compound (1+)) 0-trifluoromethylbenzoyl chloride was added to 3.0 g (18 mmol) of ferric chloride. 6g (x7 mmol)
Add 2.1 g of 0-methylanisole to the mixture under ice cooling.
(18 mmol) was added dropwise, and 20
The reaction mixture was poured into ice water and extracted with chloroform. The carrier layer was washed with 10% hydrochloric acid and saturated brine, dried over sodium sulfate, and the solvent was distilled off to obtain a The crude crystals were suspended in 50 trtl of 55% hydroiodic acid and refluxed for 10 hours.The reaction solution was cooled, and the resulting crystals were collected and washed with water.The crystals were eluted with ethyl acetate. The obtained crude crystals were dissolved in 5 ml of concentrated sulfuric acid, 1.2 trtl of concentrated nitric acid was added dropwise to the solution under ice cooling, and the mixture was stirred for 3 hours under water cooling.The reaction solution was poured into ice water and extracted with chloroform.
有機層を水洗し、硫酸ナトリウムで乾燥した後、溶媒留
去した。得られた粗結晶を酢酸エチル−ヘキサンで再結
晶化して標記化合物の淡黄色結晶４．１’Ｖ得た。収率
８３％。融点１０４〜１０５°Ｃ０
上記と同様にして化合物（２）・〜（４）を合成した。The organic layer was washed with water, dried over sodium sulfate, and then the solvent was distilled off. The obtained crude crystals were recrystallized from ethyl acetate-hexane to obtain pale yellow crystals of the title compound (4.1'V). Yield 83%. Melting point 104-105°C0 Compounds (2) to (4) were synthesized in the same manner as above.
出発物質、生成化合物、収率および融点を第１表に示す
。Starting materials, product compounds, yields and melting points are shown in Table 1.
実施例２
３−アリル−４−ヒドロキシ−５−ニトロ−２−トリフ
ルオロメチルベンゾフェノン（化合物（６１）の製造ニ
ー
４−ヒドロキシ−３−ニトロ−２′−トリフルオロメチ
ルベンゾフェノン５．０ｇ（１６ミリモル）および臭化
アリル２．５Ｆ（２０ミリモル）をアセトン５ｓｔに溶
解し、ＩＮ水酸化ナトリウム水溶液１０ｍ１および硫酸
カリウム２．２５Ｎ（１６ミリモル）を加え、１２時間
１２０”Ｃで還流した。反応混合物をエーテルで抽出し
、水で洗浄し、硫酸ナトリウムで乾燥した後、溶媒留去
した。得られた粗結晶を１８０”Ｃで５時間加熱した後
、シリカゲルカラムクロマトグラフィーを行ない、次い
で酢酸エチル−ｎ−ヘキサンで再結晶化して標記化合物
の結晶３．５ｇを得た。収率６２％。融点６３℃。Example 2 Preparation of 3-allyl-4-hydroxy-5-nitro-2-trifluoromethylbenzophenone (compound (61)) 5.0 g (16 mmol) of 4-hydroxy-3-nitro-2'-trifluoromethylbenzophenone ) and allyl bromide 2.5F (20 mmol) were dissolved in acetone 5st, 10 ml of IN aqueous sodium hydroxide solution and 2.25N (16 mmol) of potassium sulfate were added, and the mixture was refluxed at 120"C for 12 hours. The reaction mixture was After extraction with ether, washing with water, and drying with sodium sulfate, the solvent was distilled off. The obtained crude crystals were heated at 180"C for 5 hours, and then subjected to silica gel column chromatography, and then ethyl acetate-n - Recrystallization from hexane gave 3.5 g of crystals of the title compound. Yield: 62%. Melting point: 63°C.
実施例３
４−アセトキン−３−メチル−５−二トロー２−トリフ
ルオロメチルベンゾフェノン（化合物ｆ９１〕の製造ニ
ー
４−ヒドロキシ−３−メチル−５−ニトロ−２“−トリ
フルオロメチルベンゾフェノン３．３１１０ミリモル）
をピリジン５ｔｓｌに溶解し、水冷上無水酢酸１．３ｇ
（１２ミリモル）を加えた後、室温で５時間攪拌した。Example 3 Preparation of 4-acetoquine-3-methyl-5-nitro-2-trifluoromethylbenzophenone (compound f91) 4-Hydroxy-3-methyl-5-nitro-2"-trifluoromethylbenzophenone 3.3110 mmol)
Dissolved in 5 tsl of pyridine and cooled with 1.3 g of acetic anhydride.
After adding (12 mmol), the mixture was stirred at room temperature for 5 hours.
反応液を氷水中に注ぎ、ベンゼンで抽出した。有機層を
２Ｎ塩酸、２Ｎ伏酸ソーダ水溶液、水で洗浄し、硫酸ナ
トリウムで乾燥した後、溶媒留去した。得られた粗結晶
を酢酸エチル−ヘキサンで再結晶化して標記化合物の結
晶３．５ｆＩを得た。収率９５％。融点１１８”Ｃ０実
施例４
３−メチル−５−ニトロ−４−（Ｎ、Ｎ−ジメチルカル
バモイルオキシ）−２−）リフルオロメチルベンゾフェ
ノン（化合物（１１））の製ａニー４−ヒドロキシー３
−メチル−５−ニトロ−２−トリフルオロメチルベンゾ
フェノン３．３ｇ（１０ミリモル）をピリジン５ゴに溶
解し、水冷下Ｎ、Ｎ−ジメチルカルバモイルクロリド１
．１ｙ（１１ミリモル）のピリジン溶液３ｔｔｔを滴下
した後、室温で２時間攪拌した。続いて実施例３と同様
の操作を行い、標記化合物の結晶３．６９を得た。収率
９１％。融点１１８”Ｃ。The reaction solution was poured into ice water and extracted with benzene. The organic layer was washed with 2N hydrochloric acid, 2N aqueous sodium acetate solution, and water, dried over sodium sulfate, and then the solvent was distilled off. The obtained crude crystals were recrystallized from ethyl acetate-hexane to obtain 3.5 fI crystals of the title compound. Yield 95%. Melting point 118''C0 Example 4 Preparation of 3-methyl-5-nitro-4-(N,N-dimethylcarbamoyloxy)-2-)lifluoromethylbenzophenone (compound (11)) ani 4-hydroxy-3
-Methyl-5-nitro-2-trifluoromethylbenzophenone (3.3 g, 10 mmol) was dissolved in pyridine (5 g), and N,N-dimethylcarbamoyl chloride (1 g) was dissolved under water cooling.
．． After dropping 3ttt of a pyridine solution of 1y (11 mmol), the mixture was stirred at room temperature for 2 hours. Subsequently, the same operation as in Example 3 was performed to obtain 3.69 crystals of the title compound. Yield 91%. Melting point 118"C.
試験例１〜５および比較試験例１〜４
１１５０００ Ｈのワグネルポットに水田土壌をつめ、
水を加えて充分攪拌し、水位が土壌表層に来るように水
はを調整した。土壌表層をならしてから３葉期の水稲の
水苗を深さ２〜３０〃になる様に移植し、さらにヒエ、
カヤツリグサ、コナギの種子を播種し、ミズ力ヤッリ、
ウリカワ、ホタルイの塊茎を置床した。次いで本発明ベ
ンゾフェノン化合物の希釈液を所定薬量になるように添
加し、湛水深を３ ｃｍに保つ。鉢を温室内に置き、温
度を剤
２０〜３０°Ｃに保つ。うＣ理１ケ月後、各ポット内の
発芽数、草丈、症状をもとに植物体の被害程度を総合的
に観察することにより試験化合物の対象雑草に対する除
草活性Ｂよびイネに対する薬害程度を評価した。結果を
第２表に示、す。なお同様の試験を対照化合物について
も行ない、結果を第３表に示す。Test Examples 1 to 5 and Comparative Test Examples 1 to 4 A 115,000 H Wagner pot was filled with paddy soil,
Add water, stir thoroughly, and adjust the water level so that it reaches the soil surface layer. After leveling the soil surface layer, transplant rice seedlings at the 3-leaf stage to a depth of 2 to 30 cm, and then
Sowing the seeds of cyperus and cyperus,
I placed tubers of Urikawa and Hotarui on the bed. Next, a diluted solution of the benzophenone compound of the present invention is added in a predetermined amount, and the flooding depth is maintained at 3 cm. Place the pot in a greenhouse and maintain the temperature at 20-30°C. After one month of treatment, the degree of damage to the plants is comprehensively observed based on the number of germinations in each pot, plant height, and symptoms to evaluate the herbicidal activity B of the test compound against the target weeds and the degree of chemical damage to rice. did. The results are shown in Table 2. A similar test was also conducted on a control compound, and the results are shown in Table 3.
除草活性は、下記の基準に従って評価した。Herbicidal activity was evaluated according to the following criteria.
評点 被害程度 ５ はとんど完全枯死 ４ 被害甚 ３ 被害多 ２ 被害中 １ 被害小 ０ 無被害 また、薬害程度は、下記の基準に従って評価した。Rating: Degree of damage 5 Almost completely withered 4. Severe damage 3. Lots of damage 2 Damaged 1. Minor damage 0 No damage In addition, the degree of drug damage was evaluated according to the following criteria.
−：薬害なし 士 ：薬害小
＋：〃 中 ＋十：〃 甚
＋十＋ ； ／／ 多 十＋十十： 〃 激（枯死）本
発明ベンゾフェノン誘導体は、従来のベンゾフェノン誘
導体に比べて少量で優れた除草活性を示し、さらに薬害
をほとんど有さないことがわかる。-: No chemical damage Person: Minor chemical damage +: Medium + 10: 〃 Significant + 10+; It can be seen that it exhibits excellent herbicidal activity and has almost no phytotoxicity.
手続補正書（峠）
■、事件の表示
昭和５９ 年特許願第 ０２９４３５ 号２゜発明の名
称
含フツ素ベンゾフェノン誘導体およびその用途３、補正
をする者
事件との関係 特許出願人
住所゛ 大阪府大阪市北区梅川１丁目１２番３９号新阪
忌Ｃル名称 （２８５）ダイキン工業株式会社代表者
山 １） 稔
４、代理人
住所 大阪府大阪市東区本町２−１０ 本町ビル内氏名
弁理士（６２１４）青 山 葆 ほか２ 名７、補正
の内容
明輝１ヂネの光ＨＩ４の詳利１な説明の１迦中、次のＩ
Ｆ、１所を補正します。Procedural amendment (toge) ■, Indication of the case Patent Application No. 029435 of 1982 2゜Name of the invention Fluorine-containing benzophenone derivatives and their uses 3, Person making the amendment Relationship with the case Patent applicant address゛ Osaka, Osaka Prefecture 1-12-39 Umekawa, Kita-ku, Ichikita-ku Shinsaka Memorial Cl Name (285) Representative of Daikin Industries, Ltd.
Yama 1) Minoru 4, Agent Address: Honmachi Building, 2-10 Honmachi, Higashi-ku, Osaka City, Osaka Name: Patent Attorney (6214) Aoyama Ao and 2 others 7: Details of the amendment: Meiki 1 Gene no Hikari HI4 Details 1 During the first part of the explanation, the next I
F. Correct one place.
（１） ７ ’Ｐ’ ４行［ブチロイルオキシＪを「ブ
チリルオキシ」２訂正。(1) 7 'P' Line 4 [Corrected butyroyloxy J to "butyryloxy" 2.
以上that's all
Claims (1)
化アルキル基、シクロアルキル基、）１０ゲンまたはア
ルケニル基を、Ｍは水素、アルカリは同一または異なっ
て、水素または低級アルキル基である。）または−５０
２−Ｒ （ここでｋ は低級アルキル基あるいは置換ま
ｔこは非置換フェニル基である。）を表わす。〕 − て示される含フツ素ベンゾフェノン誘導体。 ２、式： 〔式中、ｋは直鎖もしくは分校のアルキル基、ハロゲン
化アルキル基、ンクロアルキル基％ハｔ：’ゲンまたは
アルケニル基を、Ｍは水素、アルカリは向−または異な
って、水素または低級アルキル基である。〕またはーＳ
Ｏ −Ｒ３（ここでＲ３は低級アルキル基あるいは置換
または非置換フェニル基である。）を表わす。〕 で示される含フッ素べ゛ンゾフエノン誘導体の一種また
は二種以上を有効成分として倉荷することを特徴とする
除草組成物。[Scope of Claims] [In the formula, k is a linear or branched alkyl group, a halogenated alkyl group, a cycloalkyl group, M is hydrogen, and the alkalis are the same or different and represent hydrogen or It is a lower alkyl group. ) or -50
2-R (where k is a lower alkyl group or substituted or unsubstituted phenyl group). ] − A fluorine-containing benzophenone derivative represented by 2. Formula: [In the formula, k is a straight-chain or branched alkyl group, a halogenated alkyl group, a chloroalkyl group, M is hydrogen, and alkali is opposite or different, hydrogen or a lower alkyl group. ] or -S
O-R3 (where R3 is a lower alkyl group or a substituted or unsubstituted phenyl group). ] A herbicidal composition containing one or more fluorine-containing benzophenone derivatives as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2943584A JPS60172946A (en) | 1984-02-17 | 1984-02-17 | Fluorine-containing benzophenone derivative and its use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2943584A JPS60172946A (en) | 1984-02-17 | 1984-02-17 | Fluorine-containing benzophenone derivative and its use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS60172946A true JPS60172946A (en) | 1985-09-06 |
Family
ID=12276055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2943584A Pending JPS60172946A (en) | 1984-02-17 | 1984-02-17 | Fluorine-containing benzophenone derivative and its use |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60172946A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5786513A (en) * | 1993-02-25 | 1998-07-28 | Hoechst Aktiengesellschaft | Inhibitors of hydroxyphenylpyruvate dioxygenase and an assay for identification of inhibitors |
| US6110963A (en) * | 1998-05-12 | 2000-08-29 | American Home Products Corporation | Aryl-oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6214877B1 (en) | 1998-05-12 | 2001-04-10 | John A. Butera | 2,3,5-substituted biphenyls useful in the treatment of insulin resistance and hyperglycemia |
| US6221902B1 (en) | 1998-05-12 | 2001-04-24 | American Home Products Corporation | Biphenyl sulfonyl aryl carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6232322B1 (en) | 1998-05-12 | 2001-05-15 | American Home Products Corporation | Biphenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6310081B1 (en) | 1999-05-10 | 2001-10-30 | American Home Products Corporation | Biphenyl sulfonyl aryl carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6451827B2 (en) | 1998-05-12 | 2002-09-17 | Wyeth | 2,3,5-substituted biphenyls useful in the treatment of insulin resistance and hyperglycemia |
| US6699896B1 (en) | 1998-05-12 | 2004-03-02 | Wyeth | Oxazole-aryl-carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
-
1984
- 1984-02-17 JP JP2943584A patent/JPS60172946A/en active Pending
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5786513A (en) * | 1993-02-25 | 1998-07-28 | Hoechst Aktiengesellschaft | Inhibitors of hydroxyphenylpyruvate dioxygenase and an assay for identification of inhibitors |
| US6555714B1 (en) | 1993-02-25 | 2003-04-29 | Hoechst Aktiengesellschaft | Inhibitors of hydroxyphenylpyruvate dioxygenase and an assay for identification of inhibitors |
| US6221902B1 (en) | 1998-05-12 | 2001-04-24 | American Home Products Corporation | Biphenyl sulfonyl aryl carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6214877B1 (en) | 1998-05-12 | 2001-04-10 | John A. Butera | 2,3,5-substituted biphenyls useful in the treatment of insulin resistance and hyperglycemia |
| US6232322B1 (en) | 1998-05-12 | 2001-05-15 | American Home Products Corporation | Biphenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6369072B2 (en) | 1998-05-12 | 2002-04-09 | American Home Products Corporation | Biphenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6391897B2 (en) | 1998-05-12 | 2002-05-21 | American Home Products Corporation | Biphenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6451827B2 (en) | 1998-05-12 | 2002-09-17 | Wyeth | 2,3,5-substituted biphenyls useful in the treatment of insulin resistance and hyperglycemia |
| US6110963A (en) * | 1998-05-12 | 2000-08-29 | American Home Products Corporation | Aryl-oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6699896B1 (en) | 1998-05-12 | 2004-03-02 | Wyeth | Oxazole-aryl-carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6765021B2 (en) | 1998-05-12 | 2004-07-20 | Wyeth | 2,3,5-substituted biphenyls useful in the treatment of insulin resistance and hyperglycemia |
| US7008636B2 (en) | 1998-05-12 | 2006-03-07 | Wyeth | 2,3,5-substituted biphenyls useful in the treatment of insulin resistance and hyperglycemia |
| US7141672B2 (en) | 1998-05-12 | 2006-11-28 | Wyeth | Oxazole-aryl-carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
| US6310081B1 (en) | 1999-05-10 | 2001-10-30 | American Home Products Corporation | Biphenyl sulfonyl aryl carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
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