JPH04164004A - Method for stabilizing sexual pheromone compound - Google Patents
Method for stabilizing sexual pheromone compoundInfo
- Publication number
- JPH04164004A JPH04164004A JP2288749A JP28874990A JPH04164004A JP H04164004 A JPH04164004 A JP H04164004A JP 2288749 A JP2288749 A JP 2288749A JP 28874990 A JP28874990 A JP 28874990A JP H04164004 A JPH04164004 A JP H04164004A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pheromone
- acetate
- unsaturated double
- general formula
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 21
- 239000003016 pheromone Substances 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 9
- 230000000087 stabilizing effect Effects 0.000 title claims description 7
- 230000001568 sexual effect Effects 0.000 title abstract 4
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 claims abstract description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 11
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims abstract 3
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 claims abstract 3
- 239000000877 Sex Attractant Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 6
- MUZGQHWTRUVFLG-SREVYHEPSA-N 7Z-Dodecenyl acetate Chemical compound CCCC\C=C/CCCCCCOC(C)=O MUZGQHWTRUVFLG-SREVYHEPSA-N 0.000 abstract description 2
- MUZGQHWTRUVFLG-UHFFFAOYSA-N Z7-12:OAc Natural products CCCCC=CCCCCCCOC(C)=O MUZGQHWTRUVFLG-UHFFFAOYSA-N 0.000 abstract description 2
- 230000006641 stabilisation Effects 0.000 abstract 2
- 238000011105 stabilization Methods 0.000 abstract 2
- RFEQLTBBKNKGGJ-DEQVHDEQSA-N 9Z,11E-Tetradecadienyl acetate Chemical compound CC\C=C\C=C/CCCCCCCCOC(C)=O RFEQLTBBKNKGGJ-DEQVHDEQSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 10
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- 150000001565 benzotriazoles Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 3
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- GPMCZKILFBRNNY-UHFFFAOYSA-N 2,3-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=C(O)C=CC(O)=C1C(C)(C)CC GPMCZKILFBRNNY-UHFFFAOYSA-N 0.000 description 2
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 2
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 2
- XXPBOEBNDHAAQH-SREVYHEPSA-N 9Z-Tetradecenyl acetate Chemical compound CCCC\C=C/CCCCCCCCOC(C)=O XXPBOEBNDHAAQH-SREVYHEPSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- OZEUSMXTSJPCQI-AATRIKPKSA-N (9e)-dodeca-9,11-dien-3-ol Chemical compound CCC(O)CCCCC\C=C\C=C OZEUSMXTSJPCQI-AATRIKPKSA-N 0.000 description 1
- CDPKRQSIFVWEFL-UHFFFAOYSA-N 1-[3-(benzotriazol-2-yl)-5-butylphenyl]butan-2-ol Chemical compound OC(CC=1C=C(C=C(C1)N1N=C2C(=N1)C=CC=C2)CCCC)CC CDPKRQSIFVWEFL-UHFFFAOYSA-N 0.000 description 1
- YJINQJFQLQIYHX-PLNGDYQASA-N 11Z-Tetradecenyl acetate Chemical compound CC\C=C/CCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-PLNGDYQASA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- SUCYDSJQVVGOIW-WAYWQWQTSA-N 8Z-Dodecenyl acetate Chemical compound CCC\C=C/CCCCCCCOC(C)=O SUCYDSJQVVGOIW-WAYWQWQTSA-N 0.000 description 1
- MFFQOUCMBNXSBK-PLNGDYQASA-N 9Z-Dodecenyl acetate Chemical compound CC\C=C/CCCCCCCCOC(C)=O MFFQOUCMBNXSBK-PLNGDYQASA-N 0.000 description 1
- 101000885703 Taxus cuspidata 2-alpha-hydroxytaxane 2-O-benzoyltransferase Proteins 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- -1 Z-9-tetrazocenol Chemical compound 0.000 description 1
- DUCVQKMNGSZPAV-ZHACJKMWSA-N [(e)-tridec-4-enyl] acetate Chemical compound CCCCCCCC\C=C\CCCOC(C)=O DUCVQKMNGSZPAV-ZHACJKMWSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- HVUBXNQWXJBVHB-UHFFFAOYSA-N icos-13-en-10-one Chemical compound CCCCCCCCCC(=O)CCC=CCCCCCC HVUBXNQWXJBVHB-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、交信撹乱防除法による害虫の能除に有用な、
不飽和二重結合を有する高級脂肪族性フェロモン化合物
の安定化方法に関するものである。[Detailed Description of the Invention] (Industrial Application Field) The present invention provides a
The present invention relates to a method for stabilizing higher aliphatic pheromone compounds having unsaturated double bonds.
（従来の技術）
近年、殺虫剤等の農薬はそれを扱う者に対する毒性が大
きく一つの社会問題に発展している。この問題に対処す
るため、生物学的害虫防除法が研究されており、この方
法の一つとして害虫の雌が放出する性フェロモンを化学
的に合成し、これを利用する交信撹乱防除法が提案され
ている。この防除法においては特公昭６１−１．６３６
］号公報に記載の徐放体のように性フェロモンを長期間
一定の量放出させることが必要である。しかし、リンシ
目害虫の性フェロモン物質の多くは不飽和二重結合を有
する高級脂肪族誘導体であるため、長期間野外条件下に
放置すると、二重結合が容易に酸化、異性化および重合
などで変質してしまい、当初の目的が達成されなくなる
という問題がある。これを防ぐため製剤中に酸化防止剤
や紫外線吸収剤を添加する方法が提案された。例えば、
Ｊｏｕｒｎａｌ、 ｏｆＣｈｅｍｉｃａｌ Ｅｃｏｌｏ
ｇＬ Ｖｏｌ、］４． Ｎｏ、８．１６５９（１９８８
）には、酸化防止剤としてブチルヒドロキシトルエンや
ブチルヒドロキシアニソールを使用し、これに２−ヒド
ロキシ−４−メトキシベンゾフェノンなどの紫外線吸収
剤を性フェロモン物質に添加使用すると、さらに安定性
が向上すると報告されている。(Prior Art) In recent years, agricultural chemicals such as insecticides have developed into a social problem due to their toxicity to those who handle them. To deal with this problem, biological pest control methods are being researched, and one proposed method is to chemically synthesize sex pheromones released by female pests and use this to control communication disruption. has been done. In this pest control method,
It is necessary to release a constant amount of sex pheromones over a long period of time, as in the sustained-release formulation described in the above publication. However, many of the sex pheromone substances of Lymphoptera pests are higher aliphatic derivatives with unsaturated double bonds, so if left in the field for a long time, the double bonds can easily undergo oxidation, isomerization, and polymerization. There is a problem in that it changes in quality and the original purpose is no longer achieved. To prevent this, a method of adding antioxidants and ultraviolet absorbers to the formulation has been proposed. for example,
Journal, ofChemical Ecolo
gL Vol,]4. No. 8.1659 (1988
), it is reported that the stability is further improved by using butylated hydroxytoluene or butylated hydroxyanisole as an antioxidant and adding a UV absorber such as 2-hydroxy-4-methoxybenzophenone to the sex pheromone substance. has been done.
確かに特定の酸化防止剤や紫外線吸収剤では、単独で使
用するよりも混合使用の方が不飽和二重結合を有する性
フェロモン化合物の安定性の向上に役立つが、数多くの
酸化防止剤と紫外線吸収剤をどのように組合せると最も
有効かということまでは知られていない。Although it is true that the use of certain antioxidants and UV absorbers in combination helps improve the stability of sex pheromone compounds with unsaturated double bonds than when used alone, many antioxidants and UV absorbers It is not yet known what combination of absorbents is most effective.
（発明が解決しようとする課題）
したがって、本発明の目的は不飽和二重結合を有する性
フェロモン化合物の安定性の向上に有用な添加物の組合
せを提供するにある。(Problems to be Solved by the Invention) Therefore, an object of the present invention is to provide a combination of additives useful for improving the stability of sex pheromone compounds having unsaturated double bonds.
（課題を解決するための手段）
本発明による不飽和二重結合を有する高級脂肪族性フェ
ロモン化合物の安定化方法は、一般式■○Ｈ
で示されるヒドロキノン誘導体（ここにＲ１はｔ−ブチ
ル基またはｔ−アミル基を、Ｒ２は水素原子。(Means for Solving the Problems) The method for stabilizing a higher aliphatic pheromone compound having an unsaturated double bond according to the present invention uses a hydroquinone derivative represented by the general formula ■○H (where R1 is a t-butyl group). or t-amyl group, R2 is a hydrogen atom.
ｔ−ブチル基またはｔ−アミル基を示す）と、一般式■
で示されるベンゾトリアゾール誘導体（ここにＸは水素
または塩素原子、Ｒ３およびＲ４はそれぞれｔ−ブチル
基またはｔ−アミル基を示す）とを、添加混合すること
を要旨とするものである。(represents a t-butyl group or a t-amyl group), and a benzotriazole derivative represented by the general formula (where X is a hydrogen or chlorine atom, and R3 and R4 each represent a t-butyl group or a t-amyl group) The gist is to add and mix the following.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明において上記一般式Ｉで示されるヒドロキノン誘
導体としては、ｔ−ブチルヒドロキノン、ジ−ｔ−ブチ
ルヒドロキノン、ジ−ｔ−アミルヒドロキノンなどが例
示される。一般にヒドロキノン化合物はブチルヒドロキ
シトルエン、ブチルヒドロキシアニソール、ビタミンＥ
のような酸化防止剤と比べて性フェロモン化合物中の二
重結合に対して酸化防止のみならず重合や異性化に対し
て有効である。しかし、本発明で使用するｔ−ブチル基
やｔ−アミル基を含まない、ヒドロキノンやメチルヒド
ロキノンなどのヒドロキノン化合物は、高級脂肪族誘導
体である性フェロモンと相溶性が悪く、その効果を充分
に発揮出来ない。また、これらのヒドロキノン化合物は
単独で使用しても野外の直射日光下で充分な効果が発揮
されない。そこで、本発明者らは、これらのヒドロキノ
ン化合物と混合して、最も効果を発揮できる紫外線吸収
剤を検討したところ、一般式■で示されるベンゾトリア
ゾール誘導体との組合せが最適であることを見出した。In the present invention, examples of the hydroquinone derivative represented by the above general formula I include t-butylhydroquinone, di-t-butylhydroquinone, and di-t-amylhydroquinone. Generally, hydroquinone compounds include butylated hydroxytoluene, butylated hydroxyanisole, and vitamin E.
Compared to antioxidants such as, it is effective not only in preventing oxidation of double bonds in sex pheromone compounds, but also in polymerization and isomerization. However, the hydroquinone compounds used in the present invention, such as hydroquinone and methylhydroquinone, which do not contain t-butyl or t-amyl groups, have poor compatibility with sex pheromones, which are higher aliphatic derivatives, and cannot fully exert their effects. Can not. Further, even if these hydroquinone compounds are used alone, they do not exhibit sufficient effects outdoors under direct sunlight. Therefore, the present inventors investigated which ultraviolet absorber can be most effective when mixed with these hydroquinone compounds, and found that the combination with a benzotriazole derivative represented by the general formula (■) is optimal. .
ベンゾトリアゾール誘導体も各種のものが知られている
が、Ｒ３およびＲ４としてｔ−ブチル基またはｔ−アミ
ル基を有するものが性フェロモンとの相溶性に優れてい
て最も有効であることが判った。Although various benzotriazole derivatives are known, those having t-butyl or t-amyl groups as R3 and R4 have been found to be the most effective because they have excellent compatibility with sex pheromones.
これには２−（２’−ヒドロキシ−３’、５’−ジーを
一ブチルフェニル）−ベンゾトリアゾール、２−（２’
−ヒドロキシ−３’、５’−ジ−ｔ−アミルフェニル）
−ベンゾトリアゾール、２−（２’−ヒドロキシ−３’
、５’−ジーｔ−ブチルフェニル）−５−クロロベンゾ
トリアゾールなどが例示される。This includes 2-(2'-hydroxy-3',5'-di-butylphenyl)-benzotriazole, 2-(2'
-hydroxy-3',5'-di-t-amylphenyl)
-benzotriazole, 2-(2'-hydroxy-3'
, 5'-di-t-butylphenyl)-5-chlorobenzotriazole, and the like.
これらヒドロキノン誘導体およびベンゾトリアゾール誘
導体の使用量は共に性フェロモン化合物に対し０．１％
以上必要で、これ以下では効果が少なく、また３０重量
％以上使用してもこれ以上の効果の向上が見込めない。The amount of these hydroquinone derivatives and benzotriazole derivatives used is both 0.1% based on the sex pheromone compound.
If the amount is less than this amount, the effect will be small, and even if it is used in an amount of 30% by weight or more, no further improvement in the effect can be expected.
本発明が適用される不飽和二重結合に有する高級脂肪族
性フェロモン化合物には、Ｚ−７−ドデセニルアセテー
ト、Ｚ−８−ドデセニルアセテート、Ｚ−９−ドデセニ
ルアセテート、Ｅ、Ｚ〜７．９−ドデカジェニルアセテ
ート、Ｅ、Ｅ〜８．１０−ドデカジエノール、Ｅ−４−
トリデセニルアセテート、ｚ−９−テトラデセニルアセ
テート、Ｚ−９−テトラゾセノール、Ｚ−１１−テトラ
デセニルアセテート、Ｚ、Ｅ−９，１１−テトラデカジ
ェニルアセテート、Ｚ、Ｅ−９゜１２−テトラデカジェ
ニルアセテート、ｚ−ｉｉ−へキサデセニルアセテート
、Ｚ、Ｚ−７，１１−へキサデカジェニルアセテート、
Ｅ、Ｅ、Ｚ−４，６，１０−ヘキサデ力トリエニルアセ
テート、Ｅ、Ｅ−１０，１２−へキサデカジェナール、
Ｚ、Ｚ−３，１３−オクタデカジェニルアセテート、Ｅ
、Ｚ−３，１３−オクタデカジェニルアセテート、Ｚ、
１３−イコセンー１０−オンなどが例示される。これら
の中でも通常不安定とされている、不飽和二重結合が２
個以上含む化合物に対して本発明の安定効果が高い。Higher aliphatic pheromone compounds having an unsaturated double bond to which the present invention is applied include Z-7-dodecenyl acetate, Z-8-dodecenyl acetate, Z-9-dodecenyl Acetate, E, Z~7.9-dodecadenyl acetate, E, E~8.10-dodecadienol, E-4-
Tridecenyl acetate, z-9-tetradecenyl acetate, Z-9-tetrazocenol, Z-11-tetradecenyl acetate, Z, E-9,11-tetradecagenyl acetate, Z, E-9゜12-tetradecagenyl acetate, z-ii-hexadecenyl acetate, Z, Z-7,11-hexadecagenyl acetate,
E, E, Z-4,6,10-hexadetrienyl acetate, E, E-10,12-hexadecalenal,
Z, Z-3,13-octadecagenyl acetate, E
, Z-3,13-octadecagenyl acetate, Z,
Examples include 13-icosene-10-one. Among these, unsaturated double bonds, which are usually considered unstable, are
The stabilizing effect of the present invention is high for compounds containing more than 1.
本発明において安定剤として使用するヒドロキノン誘導
体とベンゾトリアゾール誘導体は、それらがそれぞれ１
種以上混合されることが重要であり、この混合物に他の
安定剤をさらに混合して使用してもよい。The hydroquinone derivative and benzotriazole derivative used as stabilizers in the present invention each have a
It is important to mix more than one stabilizer, and this mixture may be further mixed with other stabilizers.
（実施例）
以下、本発明の具体的な態様を実施例および比較例によ
り説明するが１本発明はこれに限定されるものではない
。(Examples) Hereinafter, specific aspects of the present invention will be explained using Examples and Comparative Examples, but the present invention is not limited thereto.
内径１■、外径２ｍ１１、長さ２０ａｍのガラス管内に
、次表に示す性フェロモン化合物と安定剤の混合物の１
００■を充填した後、両端に栓をして野外の直射日光の
当る場所に６月から３力月間曝露した６その後、開封し
て混合液を取出し、変性しないで残存している性フェロ
モン量を内部標準法ガスクロマトグラフィーによって定
量して、充填時の性フェロモンに対する残存率を求めた
。In a glass tube with an inner diameter of 1 mm, an outer diameter of 2 m1, and a length of 20 am, 1 of the mixture of sex pheromone compound and stabilizer shown in the following table was placed.
After filling with 00■, it was plugged at both ends and exposed to direct sunlight outdoors for 3 months from June 6.Then, the package was opened and the mixed liquid was taken out, and the amount of sex pheromone remaining without denaturation was measured. was quantified by internal standard gas chromatography to determine the residual rate of sex pheromone at the time of filling.
表より、実施例の組合せでは比較例に比べ性フェロモン
の残存率が高く顕著な安定化効果のあることが判った。From the table, it was found that the combination of Examples had a higher residual rate of sex pheromones than the Comparative Example and had a remarkable stabilizing effect.
なお、各側で用いた性フェロモン、安定剤は次の通りで
ある。The sex pheromones and stabilizers used on each side are as follows.
・性フェロモン
１ ： Ｅ、Ｚ−７，９−ドデカジェニルアセテート、
Ｕ ： Ｚ、Ｚ−７，１１−ヘキサデカジェニルアセテ
ート、
ｍ ： Ｚ、Ｅ−９，１２−テトラデカジェニルアセテ
ート。・Sex pheromone 1: E, Z-7,9-dodecagenyl acetate,
U: Z, Z-7,11-hexadecagenyl acetate, m: Z, E-9,12-tetradecagenyl acetate.
ＩＶ：Ｚ−９−テトラデセニルアセテート、・安定剤
（ヒドロキノン誘導体）
ＴＢＨ：ｔ−ブチルヒドロキノン、
ＤＢＨニジ−ｔ−ブチルヒドロキノン、ＤＡＨニジ−ｔ
−アミルヒドロキノン。IV: Z-9-tetradecenyl acetate, stabilizer (hydroquinone derivative) TBH: t-butylhydroquinone, DBH di-t-butylhydroquinone, DAH di-t
-Amylhydroquinone.
（ベンゾトリアゾール誘導体）
ＨＤＢＢＴ ： ２−（２’−ヒドロキシ−３’、５’
−ジ−ｔ−ブチルフェニル）−ベンゾトリアゾール、Ｈ
ＤＡＢＴ ： ２−（２’−ヒドロキシ−３’、５’−
ジ−ｔ−アミルフェニル）−ベンゾトリアゾール、ＣＨ
ＤＢＢＴ ： ２−（２’−ヒドロキシ−３’、５’−
ジ−ｔ−ブチルフェニル）−５−クロロベンゾトリアゾ
ール、
（その他）
ＢＨＴニブチルヒドロキシトルエン、
ＢＨＡニブチルヒドロキシアニソール。(Benzotriazole derivative) HDBBT: 2-(2'-hydroxy-3', 5'
-di-t-butylphenyl)-benzotriazole, H
DABT: 2-(2'-hydroxy-3', 5'-
di-t-amylphenyl)-benzotriazole, CH
DBBT: 2-(2'-hydroxy-3',5'-
(di-t-butylphenyl)-5-chlorobenzotriazole, (others) BHT nibbutylhydroxytoluene, BHA nibbutylhydroxyanisole.
ＨＭＢＰ：２−ヒドロキシ−４−メトキシベンゾフェノ
ン。HMBP: 2-hydroxy-4-methoxybenzophenone.
（発明の効果）
本発明によれば、不飽和二重結合を有する高級脂肪族性
フェロモン化合物の安定性の向上に最も有効に作用する
。(Effects of the Invention) According to the present invention, the stability of higher aliphatic pheromone compounds having unsaturated double bonds is most effectively improved.
Claims (1)
合物に、一般式 I ▲数式、化学式、表等があります▼・・・・・・・・・
・・・一般式 I で示されるヒドロキノン誘導体（ここにＲ＾１はｔ−ブ
チル基またはｔ−アミル基を、Ｒ＾２は水素原子、ｔ−
ブチル基またはｔ−アミル基を示す）と、一般式II ▲数式、化学式、表等があります▼・・・・・・一般式
II で示されるベンゾトリアゾール誘導体（ここにＸは水素
または塩素原子、Ｒ＾３およびＲ＾４はそれぞれｔ−ブ
チル基またはｔ−アミル基を示す）とを、添加混合する
ことを特徴とする性フェロモン化合物の安定化方法。 ２、請求項１記載のヒドロキノン誘導体およびベンゾト
リアゾール誘導体が、それぞれ前記性フェロモン化合物
に対し０．１〜３０重量％の割合で添加混合されること
を特徴とする性フェロモン化合物の安定化方法。[Claims] 1. Higher aliphatic pheromone compounds having unsaturated double bonds include the general formula I ▲mathematical formula, chemical formula, table, etc.▼・・・・・・・・・
...Hydroquinone derivative represented by the general formula I (where R^1 is a t-butyl group or a t-amyl group, R^2 is a hydrogen atom, t-
butyl group or t-amyl group) and general formula II ▲Mathematical formulas, chemical formulas, tables, etc.▼・・・・・・General formula
A benzotriazole derivative represented by II (where X is a hydrogen or chlorine atom, R^3 and R^4 each represent a t-butyl group or a t-amyl group). Method for stabilizing pheromone compounds. 2. A method for stabilizing a sex pheromone compound, characterized in that the hydroquinone derivative and benzotriazole derivative according to claim 1 are added and mixed in a proportion of 0.1 to 30% by weight relative to the sex pheromone compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2288749A JP2904570B2 (en) | 1990-10-26 | 1990-10-26 | For stabilizing water-soluble pheromone compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2288749A JP2904570B2 (en) | 1990-10-26 | 1990-10-26 | For stabilizing water-soluble pheromone compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04164004A true JPH04164004A (en) | 1992-06-09 |
| JP2904570B2 JP2904570B2 (en) | 1999-06-14 |
Family
ID=17734207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2288749A Expired - Fee Related JP2904570B2 (en) | 1990-10-26 | 1990-10-26 | For stabilizing water-soluble pheromone compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2904570B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7179480B2 (en) | 2002-04-24 | 2007-02-20 | 3M Innovative Properties Company | Sustained release microcapsules |
-
1990
- 1990-10-26 JP JP2288749A patent/JP2904570B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7179480B2 (en) | 2002-04-24 | 2007-02-20 | 3M Innovative Properties Company | Sustained release microcapsules |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2904570B2 (en) | 1999-06-14 |
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