JPH0411523B2 - - Google Patents
Info
- Publication number
- JPH0411523B2 JPH0411523B2 JP57206309A JP20630982A JPH0411523B2 JP H0411523 B2 JPH0411523 B2 JP H0411523B2 JP 57206309 A JP57206309 A JP 57206309A JP 20630982 A JP20630982 A JP 20630982A JP H0411523 B2 JPH0411523 B2 JP H0411523B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- stabilizer
- general formula
- same
- 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
Links
- 239000000203 mixture Substances 0.000 claims description 17
- 239000003381 stabilizer Substances 0.000 claims description 17
- 238000003958 fumigation Methods 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 7
- 150000002989 phenols Chemical class 0.000 claims description 7
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229940035049 sorbitan monooleate Drugs 0.000 claims description 6
- 239000001593 sorbitan monooleate Substances 0.000 claims description 6
- 235000011069 sorbitan monooleate Nutrition 0.000 claims description 6
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims description 5
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- LTMQQEMGRMBUSL-UHFFFAOYSA-N Metoxadiazone Chemical compound O=C1OC(OC)=NN1C1=CC=CC=C1OC LTMQQEMGRMBUSL-UHFFFAOYSA-N 0.000 claims description 2
- -1 phenol compound Chemical class 0.000 claims 2
- 229940126062 Compound A Drugs 0.000 description 22
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000000919 ceramic Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 6
- 241000255925 Diptera Species 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 241001674044 Blattodea Species 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000002316 fumigant Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000004080 punching Methods 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Description
本発明は、安定な加熱燻蒸害虫駆除組成物に関
し、さらに詳しくは有効成分として３−（２−メ
トキシフエニル）−５−メトキシ−１，３，４−
オキサジアゾール−２（3H）−オンを含有する安
定な加熱燻蒸害虫駆除組成物に関する。
上記の３−（２−メトキシフエニル）−５−メト
キシ−１，３，４−オキサジアゾール−２（3H）
−オン（以下、化合物Ａと称す。）は、高い害虫
駆除活性を有することが知られ〔D.Ambrosi et
al（1979）：Proc.Brit.Prot.Conf、Pests and
Diseases、533頁〕ているが、安定性、特に熱安
定性に乏しく、該化合物Ａを殺虫、殺ダニ剤とし
て使用するに際し、種々の制約がある。特に、た
とえば該化合物Ａを加熱温度150℃〜350℃におい
て加熱燻蒸剤の形態で使用する場合には、その分
解が著しく、事実上その使用が不可能である。
本発明は該化合物Ａの加熱燻蒸剤としての使用
を可能にするために種々検討した結果、化合物Ａ
に下記一般式〔〕で示されるフエノール系化合
物および／またはソルビタンモノオレエート、あ
るいはこれらとピペロニルブトキサイドとを安定
剤として添加することにより、化合物Ａの安定性
が著しく増長され、加熱燻蒸剤としても実用化し
得ることを見出し、本発明を完成した。
（式中、R1およびR2は同一または相異なり、ヒ
ドロキシル基または基−OOC−CH＝CH2を表わ
し、R3およびR4は同一または相異なり、メチル
基またはエチル基を表わす。ただし、R1および
R2のいずれか一方はヒドロキシル基である。）
すなわち、本発明は、有効成分としての化合物
Ａと、安定剤としての上記一般式〔〕で示され
るフエノール系化合物および／またはソルビタン
モノオレエート、あるいはこれらとピペロニルブ
トキサイドとを含有する安定な加熱燻蒸害虫駆除
組成物を提供するものである。
本発明組成物は、加熱燻蒸形態での使用におい
ても化合物Ａの持つ高い殺虫、殺ダニ効力を損う
ことなく、たとえばイエバエ、蚊、ゴキブリ、ア
ブラムシ、ウンカ、ダニ類などの種々の害虫駆除
において卓効を発揮する。
以下に本発明の組成物について詳細に説明す
る。
本発明組成物において、安定剤として用いられ
る下記一般式〔〕で示されるフエノール系化合
物の例としては、以下のようなものがあげられ
る。
The present invention relates to stable thermal fumigation pest control compositions, and more particularly to 3-(2-methoxyphenyl)-5-methoxy-1,3,4- as an active ingredient.
A stable thermal fumigation pest control composition containing oxadiazol-2(3H)-one. The above 3-(2-methoxyphenyl)-5-methoxy-1,3,4-oxadiazole-2(3H)
-one (hereinafter referred to as compound A) is known to have high pest control activity [D. Ambrosi et al.
al (1979): Proc.Brit.Prot.Conf, Pests and
Diseases, p. 533], however, it has poor stability, especially thermal stability, and there are various limitations when using Compound A as an insecticide or acaricide. In particular, when Compound A is used in the form of a heating fumigant at a heating temperature of 150 DEG C. to 350 DEG C., its decomposition is so severe that it is virtually impossible to use it. As a result of various studies to enable the use of Compound A as a heat fumigant, the present invention has developed Compound A.
By adding a phenolic compound represented by the following general formula [] and/or sorbitan monooleate, or these and piperonyl butoxide as a stabilizer to the compound A, the stability of compound A is significantly increased, making it difficult to heat fumigation. The present invention was completed based on the discovery that it could be put to practical use as a drug. (In the formula, R 1 and R 2 are the same or different and represent a hydroxyl group or a group -OOC-CH=CH 2 , and R 3 and R 4 are the same or different and represent a methyl group or an ethyl group. However, R 1 and
Either one of R 2 is a hydroxyl group. ) That is, the present invention contains Compound A as an active ingredient, a phenolic compound represented by the above general formula [ ] and/or sorbitan monooleate, or these and piperonyl butoxide as a stabilizer. A stable thermal fumigation pest control composition is provided. The composition of the present invention can be used in the form of heat fumigation without impairing the high insecticidal and acaricidal efficacy of Compound A, and is effective in exterminating various pests such as house flies, mosquitoes, cockroaches, aphids, planthoppers, and mites. Demonstrates outstanding effectiveness. The composition of the present invention will be explained in detail below. Examples of the phenolic compound represented by the following general formula [] used as a stabilizer in the composition of the present invention include the following.
【表】
(注) 上記一般式〓〓で示される化合物の置換
基R１，R２，R３およびR４の内容。
本発明において安定剤として使用される上記フ
エノール系化合物、ソルビタンモノオレエートま
たはピペロニルブトキサイドの量（重量）は、化
合物Ａに対し、安定剤総量で、その20分の１量か
ら２倍量を用いることができるが、好ましくはそ
の10分の１量から等量である。
本発明組成物により得られる製剤形態として
は、たとえば蚊取線香基材中に本発明組成物を練
り込み線香状にうちぬくことによつて蚊取線香と
したり、本発明組成物を有機溶剤に溶解させた液
をパルプマツトに含浸させ、必要に応じ香料等を
加えて電気マツト用マツトとしたり、本発明組成
物をタルク、クレイ等の無機担体と練合し、顆粒
剤としてこれを使用時加熱される容器の中に入れ
燻蒸剤としたり、または本発明組成物を石綿、セ
ラミツク、アルミナ等の小型ブロツクに含浸さ
せ、使用時事電気加熱により燻蒸させる等の形態
があげられる。
次に実施例をあげて、本発明をさらに詳細に説
明するが、本発明はこれら実施例に限定されるも
のではない。
実施例 １
化合物A500mgと化合物番号(1)で示されるフエ
ノール系安定剤200mgとをアセトン２mlに溶解し、
これを４cm角、厚さ1.2cmのセラミツク製多孔ブ
ロツクに含浸させ、電気加熱燻蒸用製剤を得る。
実施例 ２
化合物A100mg、化合物番号(3)で示されるフエ
ノール系安定剤50mgおよび少量の香料をヘキサン
１mlに溶解し、これを通常の電気マツト用パルプ
マツトに含浸させ、電気マツト製剤を得る。
実施例 ３
化合物A100mgと化合物番号(4)で示されるフエ
ノール系安定剤50mgとを蚊取線香基材と共に練合
し、線香状にうちぬくことによつて蚊取線香製剤
を得る。
実施例 ４
下記表に示す各々の量の化合物Ａと化合物番号
(2)で示されるフエノール系安定剤とを２mlのアセ
トンに溶解し、これを４cm角、厚さ1.2cmのセラ
ミツク製多孔板に含浸させる。これらの製剤を用
いて以下に述べる方法で殺虫効力を試験したとこ
ろ、下記表に示すようなきわめて良好な殺虫効果
を得た。
殺虫効力試験方法：チヤバネゴキブリ成虫10頭を
入れた腰高ガラスシヤーレ（径14cm、高さ７
cm）を28m3の居室内の床面上に４隅に設置し、
そのうち２つのガラスシヤーレは全くふたをせ
ず、残りの２つのガラスシヤーレは上部開放部
の全面績を５分の４を被うふたを載せる。その
28m3居室内中央部に温度調節可能な電気加熱器
を設置し、前述の薬剤処理セラミツク製多孔板
を載せ、電気加熱器に通電し、一定の加熱温度
にて燻蒸する。60分後ゴキブリを回収し、新容
器に移し、24時間餌と水を与え飼育後の致死率
をみた。[Table] (Note) Contents of substituents R 1 , R 2 , R 3 and R 4 of the compound represented by the above general formula 〓〓.
The amount (weight) of the above-mentioned phenolic compound, sorbitan monooleate or piperonyl butoxide used as a stabilizer in the present invention is 1/20 to 2 times the total amount of stabilizer relative to Compound A. Any amount can be used, but preferably from one-tenth to an equivalent amount. The formulations obtained from the composition of the present invention include, for example, making a mosquito coil by kneading the composition of the present invention into a mosquito coil base material and punching it out in the shape of an incense coil, or by applying the composition of the present invention to an organic solvent. Pulp mats are impregnated with the dissolved liquid and perfumes are added as needed to make mats for electric mats, or the composition of the present invention is kneaded with an inorganic carrier such as talc or clay and heated as granules when used. The composition of the present invention may be impregnated into a small block of asbestos, ceramic, alumina, etc. and then fumigated by electric heating. Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples. Example 1 500 mg of compound A and 200 mg of the phenolic stabilizer shown by compound number (1) were dissolved in 2 ml of acetone,
This is impregnated into a ceramic porous block 4 cm square and 1.2 cm thick to obtain a preparation for electrical heating fumigation. Example 2 100 mg of Compound A, 50 mg of the phenolic stabilizer represented by Compound No. (3), and a small amount of fragrance are dissolved in 1 ml of hexane, and a conventional pulp mat for electric mats is impregnated with this solution to obtain an electric mat formulation. Example 3 A mosquito coil preparation is obtained by kneading 100 mg of Compound A and 50 mg of the phenolic stabilizer represented by Compound No. (4) with a mosquito coil base material and punching the mixture into the shape of an incense stick. Example 4 Each amount of compound A and compound number shown in the table below
The phenolic stabilizer shown in (2) was dissolved in 2 ml of acetone, and a ceramic porous plate 4 cm square and 1.2 cm thick was impregnated with this solution. When these preparations were tested for insecticidal efficacy by the method described below, very good insecticidal efficacy was obtained as shown in the table below. Insecticidal efficacy test method: Waist-high glass sheath (diameter 14cm, height 7cm) containing 10 adult German cockroaches
cm) were installed in the four corners of the floor of a 28m3 living room.
Two of the glass shelves are not covered at all, and the remaining two glass shelves are fitted with lids that cover four-fifths of the entire area of the open upper part. the
A temperature-adjustable electric heater will be installed in the center of the 28m3 living room, the above-mentioned chemical-treated ceramic perforated plate will be placed on top, the electric heater will be energized, and fumigation will be carried out at a constant heating temperature. After 60 minutes, the cockroaches were collected, transferred to a new container, and fed and watered for 24 hours to determine mortality rate.
【表】
実施例 ５
化合物A500mgと化合物番号(2)で示されるフエ
ノール系安定剤100mgとを２mlのアセトンに溶解
し、これを４cm角、厚さ1.2cmのセラミツク製多
孔板に含浸させる。一方、化合物Ａのみの500mg
を２mlのアセトンに溶解し、これを同形のセラミ
ツク製多孔板に含浸させる。これらを各々、電気
加熱器に設置し、250℃および300℃にて加熱す
る。加熱器の上につり鏡状ロートをおき、これか
ら30cmの長さのリービツヒ冷却器に通じ、さらに
５ｇのシリカゲル（60−80メツシユ）をつめ両端
を綿栓したガラス管に通じるように装置を組み、
毎分20の速さで空気をこれらの装置を通じ吸引
するようにして、燻蒸された化合物Ａを捕集す
る。捕集された化合物Ａをアセトンにて抽出し、
分析して揮散率を測定した。揮散率は下記式によ
り算出した。
揮散率（％）＝捕集された化合物Ａのmg数／500×100
各条件下での揮散率は下記表のごとくであり、
化合物番号(2)のフエノール系安定剤が有効に化合
物の安定性を高め、高い揮散率を得た。[Table] Example 5 500 mg of compound A and 100 mg of the phenolic stabilizer shown by compound number (2) are dissolved in 2 ml of acetone, and a ceramic porous plate of 4 cm square and 1.2 cm thick is impregnated with this solution. On the other hand, 500mg of compound A only
was dissolved in 2 ml of acetone and impregnated into a porous ceramic plate of the same shape. Each of these is placed in an electric heater and heated at 250°C and 300°C. Place a hanging mirror funnel on top of the heater, and assemble the device so that it leads to a 30 cm long Liebig condenser, and then to a glass tube filled with 5 g of silica gel (60-80 mesh) and plugged with cotton at both ends. ,
Air is drawn through these devices at a rate of 20 per minute to collect the fumigated Compound A. Extract the collected compound A with acetone,
The volatilization rate was measured by analysis. The volatilization rate was calculated using the following formula. Volatilization rate (%) = Number of mg of collected compound A / 500 x 100 The volatilization rate under each condition is as shown in the table below,
The phenolic stabilizer of compound number (2) effectively increased the stability of the compound and obtained a high volatilization rate.
【表】
実施例 ６
化合物A500mgと化合物番号(2)で示されるフエ
ノール系安定剤またはソルビタンモノオレエート
の所定量とを２mlのアセトンに溶解し、実施例５
と同様のセラミツク製多孔板に含浸させ、実施例
５と同様の方法で揮散率を測定した。加熱温度は
300℃とした。その結果、化合物番号(2)のフエノ
ール系安定剤およびソルビタンモノオレエートの
いずれかを添加した場合、無添加のものよりも高
い揮散率を得た。[Table] Example 6 500 mg of Compound A and a predetermined amount of the phenolic stabilizer shown by compound number (2) or sorbitan monooleate were dissolved in 2 ml of acetone, and Example 5
A perforated ceramic plate similar to the above was impregnated with the solution, and the volatilization rate was measured in the same manner as in Example 5. The heating temperature is
The temperature was 300℃. As a result, when either the phenolic stabilizer of Compound No. (2) or sorbitan monooleate was added, a higher volatilization rate was obtained than when no additive was added.
【表】
実施例 ７
化合物A500mg、化合物番号(2)で示されるフエ
ノール系安定剤50mgおよびピペロニルブトキサイ
ド50mgを２mlのアセトンに溶解し、実施例５と同
様のセラミツク製多孔板に含浸させ、実施例５と
同様の方法で揮散率を測定した。加熱温度は300
℃とした。
その結果、安定剤を添加した場合の化合物Ａの
揮散率は68.3％であり、実施例６で示された安定
剤無添加の場合の揮散率40.7％に比べ高い揮散率
が得られた。[Table] Example 7 500 mg of compound A, 50 mg of the phenolic stabilizer represented by compound number (2), and 50 mg of piperonyl butoxide were dissolved in 2 ml of acetone, and the same porous ceramic plate as in Example 5 was impregnated. The volatilization rate was measured in the same manner as in Example 5. Heating temperature is 300
℃. As a result, the volatilization rate of Compound A when the stabilizer was added was 68.3%, which was higher than the volatilization rate of 40.7% shown in Example 6 when no stabilizer was added.
Claims (1)
ル）−５−メトキシ−１，３，４−オキサジアゾ
ール−２（3H）−オンと、安定剤としての下記一
般式〔〕で示されるフエノール系化合物およ
び／またはソルビタンモノオレエート、あるいは
これらとピペロニルブトキサイドとを含有するこ
とを特徴とする加熱燻蒸害虫駆除組成物。 （式中、R1およびR2は同一または相異なり、ヒ
ドロキシル基または基−OOC−CH＝CH2を表わ
し、R3およびR4は同一または相異なり、メチル
基またはエチル基を表わす。ただし、R1および
R2のいずれか一方はヒドロキシル基である。） ２ 上記一般式〔〕で示されるフエノール系化
合物が、その置換基R1およびR2が共にヒドロキ
シル基であるフエノール系化合物である特許請求
の範囲第１項に記載の組成物。 ３ 上記一般式〔〕で示されるフエノール系化
合物が、その置換基R1およびR2が共にヒドロキ
シル基であり、R3およびR4が同一であつてメチ
ル基またはエチル基であるフエノール系化合物で
ある特許請求の範囲第１項に記載の組成物。[Scope of Claims] 1 3-(2-methoxyphenyl)-5-methoxy-1,3,4-oxadiazol-2(3H)-one as an active ingredient and the following general formula as a stabilizer A thermal fumigation pest control composition characterized by containing a phenolic compound represented by [ ] and/or sorbitan monooleate, or these and piperonyl butoxide. (In the formula, R 1 and R 2 are the same or different and represent a hydroxyl group or a group -OOC-CH=CH 2 , and R 3 and R 4 are the same or different and represent a methyl group or an ethyl group. However, R 1 and
Either one of R 2 is a hydroxyl group. 2. The composition according to claim 1, wherein the phenolic compound represented by the general formula [] is a phenolic compound in which both of the substituents R 1 and R 2 are hydroxyl groups. 3. The phenol compound represented by the above general formula [] is a phenol compound in which substituents R 1 and R 2 are both hydroxyl groups, and R 3 and R 4 are the same and are methyl or ethyl groups. A composition according to certain claims 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57206309A JPS5995206A (en) | 1982-11-24 | 1982-11-24 | Stable vermin-repelling composition for thermal fumigation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57206309A JPS5995206A (en) | 1982-11-24 | 1982-11-24 | Stable vermin-repelling composition for thermal fumigation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5995206A JPS5995206A (en) | 1984-06-01 |
| JPH0411523B2 true JPH0411523B2 (en) | 1992-02-28 |
Family
ID=16521162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57206309A Granted JPS5995206A (en) | 1982-11-24 | 1982-11-24 | Stable vermin-repelling composition for thermal fumigation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5995206A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61176502A (en) * | 1985-01-30 | 1986-08-08 | Yamaide Kosan Kk | Thermally molded article for insecticidal and fungicidal use |
| KR900013848A (en) * | 1989-03-22 | 1990-10-22 | 모오리 히데오 | Insect repellent composition |
| DE4009142A1 (en) * | 1989-03-22 | 1990-09-27 | Sumitomo Chemical Co | New insecticidal compsns. - comprising a chrysanthemic acid ester, an odour-preventing cpd. and opt. an azole cpd. to prevent colour change |
| US6540991B2 (en) | 2001-04-06 | 2003-04-01 | 3M Innovative Properties Company | Stabilized active materials |
-
1982
- 1982-11-24 JP JP57206309A patent/JPS5995206A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5995206A (en) | 1984-06-01 |
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