JPS6039323B2 - Feeding damage inhibitor against wool pests - Google Patents
Feeding damage inhibitor against wool pestsInfo
- Publication number
- JPS6039323B2 JPS6039323B2 JP13937181A JP13937181A JPS6039323B2 JP S6039323 B2 JPS6039323 B2 JP S6039323B2 JP 13937181 A JP13937181 A JP 13937181A JP 13937181 A JP13937181 A JP 13937181A JP S6039323 B2 JPS6039323 B2 JP S6039323B2
- Authority
- JP
- Japan
- Prior art keywords
- feeding damage
- undecylenate
- damage inhibitor
- pests
- inhibitor against
- 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
Links
- 210000002268 wool Anatomy 0.000 title claims description 10
- 241000607479 Yersinia pestis Species 0.000 title claims description 7
- 239000003112 inhibitor Substances 0.000 title description 5
- 239000004480 active ingredient Substances 0.000 claims description 11
- FXNFFCMITPHEIT-UHFFFAOYSA-N Ethyl 10-undecenoate Chemical compound CCOC(=O)CCCCCCCCC=C FXNFFCMITPHEIT-UHFFFAOYSA-N 0.000 claims description 8
- KISVAASFGZJBCY-UHFFFAOYSA-N methyl undecenate Chemical compound COC(=O)CCCCCCCCC=C KISVAASFGZJBCY-UHFFFAOYSA-N 0.000 claims description 8
- 239000000077 insect repellent Substances 0.000 description 16
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 3
- 241000252233 Cyprinus carpio Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- ANLABNUUYWRCRP-UHFFFAOYSA-N 1-(4-nitrophenyl)cyclopentane-1-carbonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1(C#N)CCCC1 ANLABNUUYWRCRP-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- XYIANCZIPATGDH-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)-1,3,5-trioxane Chemical compound CC(C)C1OC(C(C)C)OC(C(C)C)O1 XYIANCZIPATGDH-UHFFFAOYSA-N 0.000 description 1
- HVFDUNOFZRPYST-UHFFFAOYSA-N 2-methoxy-4-prop-2-enylphenol;5-methyl-2-propan-2-ylphenol Chemical compound CC(C)C1=CC=C(C)C=C1O.COC1=CC(CC=C)=CC=C1O HVFDUNOFZRPYST-UHFFFAOYSA-N 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
- 235000017788 Cydonia oblonga Nutrition 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- XPQPWPZFBULGKT-UHFFFAOYSA-N undecanoic acid methyl ester Natural products CCCCCCCCCCC(=O)OC XPQPWPZFBULGKT-UHFFFAOYSA-N 0.000 description 1
- -1 unsaturated fatty acid ester Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】
本発明は、羊毛害虫に対する食害抑制剤に関するもので
あり、さらに詳しくいえば、羊毛害虫であるイゴ、コイ
ガ、ヒメマルカツオブシムシ、ヒメカッオブシムシなど
に対して、穣食阻害作用、忌避作用、殺虫作用などの活
性を有する１０ーゥンデシレン酸メチルェステル、エチ
ルェステルを有効成分とする食害抑制剤に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a feeding damage suppressant for wool pests, and more specifically, the present invention relates to a feeding damage inhibitor for wool pests such as grasshopper, carp moth, Japanese carp beetle, and Japanese carp beetle. The present invention relates to a feeding damage suppressant containing 10-undecylenic acid methyl ester and ethyl ester as active ingredients, which have activities such as action, repellency, and insecticidal action.
従釆、衣類用害虫に対する防虫剤としてはナフタリン、
ショウノウ、パラジクロロベンゼンなどが用いられれて
おり、なかでも殺虫効果が強くて安価であるという点で
、パラジクロロベンゼンが最も広く用いられている。し
かしながら、パラジクロロベンゼンは有機塩素系薬剤の
１種であって、生物体内に蓄積し害を与えるおそれがあ
り、その使用については規制される方向にある。As an insect repellent for clothes, naphthalene,
Camphor, paradichlorobenzene, etc. are used, and among them, paradichlorobenzene is the most widely used because it has a strong insecticidal effect and is inexpensive. However, paradichlorobenzene is a type of organic chlorine-based drug, and there is a risk that it may accumulate in living organisms and cause harm, so its use is becoming regulated.
すでに、繊維加工の防虫処理剤である有機塩素系薬剤の
アルドリン、デルドリンは、その使用が禁止されている
。したがって、近年パラジクロロベンゼンに代るべき防
虫剤あるいは忌避剤として多くの化合物又はその組合せ
が提案されている。The use of organic chlorine agents aldrin and deldrin, which are used as insect repellents for textile processing, is already prohibited. Therefore, in recent years, many compounds or combinations thereof have been proposed as insect repellents or repellents to replace paradichlorobenzene.
例えば、トリィソプロピルーＳートリオキサン又はトリ
第三ブチルーｓートリオキサンとりナロール、アネト−
ル、メントール、ケィ皮アルデヒド、チモール・オィゲ
ノール又はこれらの誘導体との組合わせを有効成分とし
た羊毛用防虫剤（特開昭５０一２４４３６号公報）、エ
ーテル結合を有する炭素数ＩＮ固の環式化合物を有効成
分とする防虫剤（特開昭５２−１１０８２３号公報）、
アダマンタン、昇華性炭化水素、及び昇華性又は揮発性
を有する極性化合物を配合して成る昇華性防虫剤（特関
昭５３−１２１９３６号公報）、ナフタリンとチモール
との組合わせを有効成分とする防虫剤（侍関昭５３−１
０９９３８号公報）、ナフタリンと２−ィソプロピル−
５ーメチルフヱノールとの組合わせを有効成分とする衣
料用防虫剤（特開昭５４一３２６２び号公報）、アセト
キシムを主成分とする衣料用防虫剤（特関昭５４一１０
１４２５号公報）、Ｑ−位に分枝を有する炭素鎖などの
置換基をもった芳香族化合物を活性成分として含有して
いる防虫剤（特閥昭５４一１１０３２１号公報）、１−
カルポンを有効成分とする芳香性防虫剤（特開昭５５一
１９２２計号公報）などが提案されている。しかしなが
ら、これらの防虫剤はいずれもパラジクロロベンゼンに
比べると高価であるとか、その防虫効果が著しく劣ると
か、あるいは揮発性が大きいため持続性が乏しいとか、
または経時変化が著しいなどの欠点を有し、実用上十分
満足しうるものとはいえない。For example, tri-isopropyl-S-trioxane or tri-tert-butyl-S-trioxane, nalol, anet-
Insect repellent for wool containing as active ingredients a combination of alcohol, menthol, cinnamic aldehyde, thymol eugenol or their derivatives (Japanese Unexamined Patent Publication No. 50-124436), a cyclic formula with an ether bond and a carbon number of IN Insect repellent containing a compound as an active ingredient (Japanese Patent Application Laid-Open No. 110823/1983),
A sublimation insect repellent containing adamantane, a sublimable hydrocarbon, and a sublimable or volatile polar compound (Special Publication No. 53-121936), an insect repellent containing a combination of naphthalene and thymol as active ingredients. Agent (Samurai Seki 53-1
09938), naphthalene and 2-isopropyl-
Insect repellent for clothing containing a combination of 5-methylphenol as an active ingredient (Japanese Unexamined Patent Publication No. 54-3262), Insect repellent for clothing containing acetoxime as the main ingredient (Special Publication No. 54-10 Sho.
1425), an insect repellent containing as an active ingredient an aromatic compound having a substituent such as a carbon chain having a branch at the Q-position (Tokubatsu Sho 54-110321), 1-
Aromatic insect repellents containing carpon as an active ingredient (Japanese Unexamined Patent Publication No. 55-1922) have been proposed. However, all of these insect repellents are more expensive than paradichlorobenzene, their insect repellent effects are significantly inferior, or their sustainability is poor due to their high volatility.
Also, it has drawbacks such as significant changes over time, and cannot be said to be fully satisfactory in practical terms.
本発明者らは、このような事情に鑑み、安価で、防虫効
果に優れかつその効果の持続性が長く、その上安全性の
高い実用的な防虫剤を開発すべ〈鋭意研究を重ねた結果
、１０−ゥンデシレン酸メチル、１０−ウンデシレン酸
エチルを有効成分として用いることにより、その目的を
達成しうろことを見出し、この知見に基づいて本発明を
完成するに至った。In view of these circumstances, the present inventors have developed a practical insect repellent that is inexpensive, has an excellent insect repellent effect, has a long-lasting effect, and is highly safe. , methyl 10-undecylenate, and ethyl 10-undecylenate as active ingredients, it was discovered that the object could be achieved, and based on this knowledge, the present invention was completed.
すなわち、本発明は、１０−ウンヂシレン酸メチル又は
１０−ウンデシレン酸エチル、若しくはその両方を有効
成分として含有することを特徴とする羊毛害虫に対する
食害抑制剤を提供するものである。That is, the present invention provides a feeding damage suppressant for wool pests, which is characterized by containing methyl 10-undecylenate, ethyl 10-undecylenate, or both as active ingredients.
本発明の食害抑制剤の有効成分である１０−ゥンデシレ
ン酸メチル、１０−ウンデシレン酸エチルは、化学構造
式ＣＨ２＝ＣＨ−（ＣＨ２）８一ＣＯＯＲ
（式中のＲはメチル基又はエチル基である）で示される
不飽和脂肪酸ェステルで、マルメロに似た風味を有し、
各種果実エッセンス用フレーバーとして用いられている
。Methyl 10-undecylenate and ethyl 10-undecylenate, which are the active ingredients of the feeding damage inhibitor of the present invention, have the chemical structural formula CH2=CH-(CH2)8-COOR (R in the formula is a methyl group or an ethyl group. ) is an unsaturated fatty acid ester with a flavor similar to quince,
It is used as a flavor for various fruit essences.
上記化合物は、１０−ウンデシレン酸とメチルアルコー
ル又はエチルアルコールとを通常用いられている方法に
従い、ェステル化反応させることによって得ることがで
きる。The above compound can be obtained by esterifying 10-undecylenic acid and methyl alcohol or ethyl alcohol according to a commonly used method.
このｌｏーウンデシレン酸メチル、１０ーウンデシレン
酸エチルは、その沸点がそれぞれ２５０ｏｏ、２６５℃
と高くて蒸気圧が小さいにもかかわらず、羊毛害虫に対
する食害抑制効力が強い。The boiling points of methyl undecylenate and ethyl 10-undecylenate are 250 oo and 265°C, respectively.
Despite its high vapor pressure and low vapor pressure, it has a strong ability to suppress feeding damage to wool pests.
この理由は、末端の二重結合の存在が活性増強の因子と
なっているものと推定される。また、蒸気圧が小さいこ
とにより、食害抑制力の持続性にも優れている。本発明
の食害抑制剤においては、１０ーウンデシレン酸メチル
又は１０ーウンデシレン酸エチルを単独で用いてもよい
し、あるいはそれらを混合して用いていてもよい。さら
に所望に応じて香料などの添加剤を配合することもでき
る。本発明の食害抑制剤はそのまま適当な容器に封入し
て用いてもよいし、またシカゲル、夕ルク、布、紙など
の支持体に担持させて使用することもできる。The reason for this is presumed to be that the presence of the terminal double bond is a factor that enhances the activity. Furthermore, due to its low vapor pressure, it has excellent sustainability of its ability to suppress feeding damage. In the feeding damage inhibitor of the present invention, methyl 10-undecylenate or ethyl 10-undecylenate may be used alone, or a mixture of them may be used. Furthermore, additives such as fragrances can be added as desired. The feeding damage inhibitor of the present invention may be used as is by being sealed in a suitable container, or may be supported on a support such as Shikagel, Yuruk, cloth, or paper.
本発明の食害抑制剤は安価であり、防虫効果に優れかつ
その効果の持続性も長く、その上安全性の高い実用的な
羊毛に対する食害抑制剤であって、イガ、コイガ、ジユ
ウタンガ、ヒメカツオブシムシ、ヒメマルカッオブシム
シなどの羊毛害虫の駆除に有効である。The feeding damage suppressant of the present invention is inexpensive, has an excellent insect repellent effect, has a long-lasting effect, and is a highly safe and practical feeding damage suppressing agent for wool. It is effective in exterminating wool pests such as the Japanese snail beetle.
次に実施例によって本発明をさらに詳細に説明する。Next, the present invention will be explained in more detail with reference to Examples.
実施例
容量５００叫の瓶の底に、１０−ウンデシレン酸メチル
又は１０−ウンデシレン酸エチル５０の９を入れ、その
５ｃｍ上方に３０日令、平均体重３０〜３５の９／１０
頭のィガ幼虫１０頭と羊毛標準試験布（２ｃの×２伽、
４０〜４５のｏ）を入れたかごを固定した。Example: Put methyl 10-undecylenate or ethyl 10-undecylenate at the bottom of a bottle with a capacity of 500 kg, and place 9/10 of methyl 10-undecylenate or ethyl 10-undecylenate 5 cm above the bottle, aged 30 days, average weight 30-35.
10 head larvae and wool standard test cloth (2 c x 2 ka,
A cage containing 40-45 o) was fixed.
次にびんを密閉し、３０ｑｏ、湿度６５％の恒温恒温室
内に７日間放置したのち、羊毛布を取り出して食害量を
測定し、虫の死亡率を教えた。虫はさらに自然状態で１
日放置し、再び死亡数を数え死亡率を求めた。その結果
をヱステルの沸点とともに次表に示す。また、比較のた
めに、他のェステル類についても実施例と同様の試験を
行い、その結果を次表に示す。Next, the bottles were sealed and left in a constant temperature room at 30 qo and 65% humidity for 7 days, after which the woolen cloth was removed and the amount of feeding damage was measured, and the mortality rate of the insects was determined. Insects are also 1 in their natural state.
After leaving it for a day, the number of deaths was counted again to determine the mortality rate. The results are shown in the table below along with the boiling point of estel. In addition, for comparison, tests similar to those in Examples were conducted on other esters, and the results are shown in the following table.
なお、表中の値は試験を５〜９回行って得られた平均値
である。Note that the values in the table are average values obtained by conducting the test 5 to 9 times.
Claims (1)
ン酸エチル、若しくはその両方を有効成分として成る羊
毛害虫に対する食害抑制剤。1. A feeding damage suppressant for wool pests comprising methyl 10-undecylenate, ethyl 10-undecylenate, or both as active ingredients.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13937181A JPS6039323B2 (en) | 1981-09-03 | 1981-09-03 | Feeding damage inhibitor against wool pests |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13937181A JPS6039323B2 (en) | 1981-09-03 | 1981-09-03 | Feeding damage inhibitor against wool pests |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5839604A JPS5839604A (en) | 1983-03-08 |
| JPS6039323B2 true JPS6039323B2 (en) | 1985-09-05 |
Family
ID=15243763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13937181A Expired JPS6039323B2 (en) | 1981-09-03 | 1981-09-03 | Feeding damage inhibitor against wool pests |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6039323B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69209386T2 (en) * | 1991-06-27 | 1996-10-02 | Atochem Elf Sa | Use of acid derivatives for the manufacture of a medication for lice |
| FR2678142A1 (en) * | 1991-06-27 | 1992-12-31 | Atochem | New composition for the treatment of pediculoses based on derivatives of undecylenic acid or undecanoic acid |
| DE4206090C2 (en) * | 1992-02-27 | 1998-02-05 | Perycut Chemie Ag | Insect repellent |
| FR2719450B1 (en) * | 1994-05-06 | 1996-05-31 | Atochem Elf Sa | Device to fight against insects. |
| FR2720897A1 (en) * | 1994-06-14 | 1995-12-15 | Atochem Elf Sa | Insecticidal compsns. |
-
1981
- 1981-09-03 JP JP13937181A patent/JPS6039323B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5839604A (en) | 1983-03-08 |
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