JPH0259502A - Insecticidal composition - Google Patents
Insecticidal compositionInfo
- Publication number
- JPH0259502A JPH0259502A JP63208843A JP20884388A JPH0259502A JP H0259502 A JPH0259502 A JP H0259502A JP 63208843 A JP63208843 A JP 63208843A JP 20884388 A JP20884388 A JP 20884388A JP H0259502 A JPH0259502 A JP H0259502A
- Authority
- JP
- Japan
- Prior art keywords
- insecticidal composition
- phenoxyphenoxy
- pyridyloxy
- propane
- diester
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 230000000749 insecticidal effect Effects 0.000 title claims abstract description 15
- 150000005690 diesters Chemical class 0.000 claims abstract description 9
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 7
- -1 1,3-dithiolan-2-ylidenemalonic acid diester Chemical class 0.000 claims abstract description 6
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 claims abstract description 3
- OOXAOGPOOQJTER-UHFFFAOYSA-N 2-(1,3-dithiolan-2-ylidene)propanedioic acid Chemical compound OC(=O)C(C(O)=O)=C1SCCS1 OOXAOGPOOQJTER-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 239000004480 active ingredient Substances 0.000 abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 abstract description 4
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
- 230000002195 synergetic effect Effects 0.000 abstract description 2
- 239000002267 larvicidal agent Substances 0.000 abstract 1
- 231100000614 poison Toxicity 0.000 abstract 1
- 230000007096 poisonous effect Effects 0.000 abstract 1
- 241000255925 Diptera Species 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000009547 development abnormality Effects 0.000 description 1
- JCKRRRSDPZOMBF-UHFFFAOYSA-N diethyl 2-(1,3-dithiolan-2-ylidene)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=C1SCCS1 JCKRRRSDPZOMBF-UHFFFAOYSA-N 0.000 description 1
- 230000032669 eclosion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
[目的]
(産業上の利用分野)
本発明は、■−(4−フェノキシフェノキシ)−2−(
2−ピリジルオキシ)プロパンと、1,3−ジチオラン
−2−イリデンマロン酸のジエステルとを含有する殺虫
組成物に関する。[Detailed description of the invention] [Purpose] (Industrial application field) The present invention is directed to ■-(4-phenoxyphenoxy)-2-(
The present invention relates to an insecticidal composition containing 2-pyridyloxy)propane and a diester of 1,3-dithiolane-2-ylidenemalonic acid.
(当該発明が解決しようとする課題等)近年、有機リン
酸エステル系、カーバメート系、ピレスロイド系等め種
々の殺虫剤に対し抵抗性を示す有害虫の出現が問題とさ
れており、それらの的確な防除が課題となっている。(Problems to be solved by the invention, etc.) In recent years, the emergence of harmful insects that are resistant to various insecticides such as organophosphate, carbamate, and pyrethroid insecticides has become a problem, and it is difficult to accurately identify them. Prevention is an issue.
このような抵抗性の問題は、農業分野にとどまらず、ハ
エや蚊のような衛生害虫でも認められ、特に各種薬剤に
対し抵抗性を獲得したハエが出現してきている。Such resistance problems are not limited to the agricultural field, but are also recognized in sanitary pests such as flies and mosquitoes, and in particular, flies that have acquired resistance to various chemicals are emerging.
一般に、抵抗性と感受性の害虫は混合状態で生息してい
るが、本発明者らは、抵抗性の度合にかかわらず、害虫
を的確に防除し得る方法を検討したところ、1−(4−
フェノキシフェノキシ)−2−(2−ピリジルオキシ)
プロパンと、1,3−ジチオラン−2−イリデンマロン
酸のジエステルとを併用することにより、害虫、特にハ
エの幼虫を極めて効率的に防除できることを見いだした
。Generally, resistant and susceptible pests live in a mixed state, but the present inventors investigated a method that can accurately control pests regardless of the degree of resistance, and found that 1-(4-
phenoxyphenoxy)-2-(2-pyridyloxy)
It has been found that by using propane and a diester of 1,3-dithiolan-2-ylidenemalonic acid in combination, pests, especially fly larvae, can be controlled very efficiently.
本発明の殺虫組成物の一方の有効成分である1−(4−
フェノキシフェノキシ)−2−(2−ピリジルオキシ)
プロパン(以下ビリプロキシフェンと称する)は昆虫の
発育異常を誘導し殺虫活性を示すことは、特開昭59−
199673号公報に公知である。1-(4-
phenoxyphenoxy)-2-(2-pyridyloxy)
Propane (hereinafter referred to as biliproxyfen) induces developmental abnormalities in insects and exhibits insecticidal activity.
It is publicly known from the publication No. 199673.
又、本発明の他方の有効成分である1、3−ジチオラン
−2−イリデンマロン酸のジエステル類も害虫防除剤と
して特公昭52−4609号公報に公知である。Furthermore, diesters of 1,3-dithiolan-2-ylidenemalonic acid, which are the other active ingredients of the present invention, are also known as pest control agents in Japanese Patent Publication No. 4609/1983.
しかしながら本発明の殺虫組成物は、下記の実施例に示
される通り、各々の単剤から予測し得ない優れた相乗的
殺虫効果を示すことから、種々の場面において適用しう
る。However, as shown in the Examples below, the insecticidal composition of the present invention exhibits an excellent synergistic insecticidal effect that cannot be expected from each single agent, and therefore can be applied in various situations.
1.3−ジチオラン−2−イリデンマロン酸のジエステ
ルとしては、例えば低級アルキルエステル、低級アルケ
ニルエステル及びベンジルエステル等を挙げることがで
きる・
低級アルキルエステルどしては、例えばメチル、エチル
、プロピル、イソプロピル、ブチル、イソブチル等の炭
素数1乃至4個のアルキルエステルが、又、低級アルケ
ニルエステルとし・では、例えばアリル、メチルアリル
等の炭素数2乃至4個のアルケニルエステルを挙げるこ
とができる。Examples of diesters of 1.3-dithiolane-2-ylidenemalonic acid include lower alkyl esters, lower alkenyl esters, and benzyl esters. Examples of lower alkyl esters include methyl, ethyl, propyl, isopropyl, Examples of lower alkenyl esters include alkyl esters having 1 to 4 carbon atoms such as butyl and isobutyl, and alkenyl esters having 2 to 4 carbon atoms such as allyl and methylallyl.
ジエステルを構成する2個のアルコール残基は同種であ
っても異種であってもよいが、同種の場合がより好適で
あり、同種のアルキルエステルの場合がさらに好適であ
り、最も好適なものはジイソプロピルエステル(以下イ
ソブロチオランと称する。)である。The two alcohol residues constituting the diester may be of the same type or different types, but it is more preferable that the two alcohol residues are of the same type, and even more preferable that they are the same type of alkyl ester, and the most preferable one is It is diisopropyl ester (hereinafter referred to as isobrothiolane).
本発明の殺虫組成物は通常の方法に従って、2種の有効
成分化合物を適当な担体及び/又は補助剤と混合するこ
とにより、この分野で慣用の剤型、例えば水和剤、ドラ
イフロアブル製剤、粉剤、粒剤、乳剤等に調製すること
ができる。The insecticidal composition of the present invention can be prepared by mixing the two active ingredient compounds with suitable carriers and/or adjuvants according to a conventional method, and can be prepared in the form of a formulation commonly used in this field, such as a wettable powder, a dry flowable formulation, or a dry flowable formulation. It can be prepared into powders, granules, emulsions, etc.
本発明の殺虫組成物中の2種の有効成分の比率は大幅に
変化させることができる。一般にいって、ビリプロキシ
フェン1部に対して、1,3−ジチオラン−2−イリデ
ンマロン酸のジエステルが1部ないし100部程度であ
る。The ratio of the two active ingredients in the insecticidal compositions of the invention can vary widely. Generally speaking, the diester of 1,3-dithiolane-2-ylidenemalonic acid is used in an amount of about 1 part to 100 parts per 1 part of biliproxyfen.
本発明の目的を達成するには、上述のような2種の有効
成分を同時に含有する組成物とすることが最適であるが
、各々の単剤を使用時に混合してもよいし、場合によっ
ては、各々の単剤を若干の時間をずらして別々に処理し
ても目的を達成することができる。In order to achieve the purpose of the present invention, it is optimal to create a composition that simultaneously contains the two types of active ingredients as described above, but each single agent may be mixed at the time of use, or in some cases The purpose can be achieved even if each single agent is treated separately at a slightly different time.
本発明の殺虫組成物は種々の場面において適用すること
ができるが、ハエの防除剤、殊に、殺うじ剤として使用
するのが最も好ましい。Although the insecticidal composition of the present invention can be applied in various situations, it is most preferably used as a fly control agent, particularly as a insecticide.
以下に本発明を実施例によって更に詳細に説明する。The present invention will be explained in more detail below with reference to Examples.
尖施但上
小麦ふすま1部、実験動物用粉末飼料(船橋農場KK)
1部の混合物に対し、同重量の水にイソプロチオ921
0%水和剤とビリプロキシフェンの10%水和剤を適宜
混合分散させた希釈液を加えて攪拌し、それを餌として
プラスチックカップ(上向径6 cm、底内径4.6
cm、内高4 cm)に入れ、混合系統イエバエの2日
令幼虫を20頭を放し、26°C±1°Cに保って成虫
の羽化率を調べ、対照区の羽化率によって補正した非羽
化率を羽化阻害率とした。1 part of Chise Tanjo wheat bran, powdered feed for experimental animals (Funabashi Farm KK)
For one part of the mixture, add isoprothio 921 to the same weight of water.
A diluted solution of 0% hydrating powder and 10% hydrating powder of biliproxyfen mixed and dispersed as appropriate was added and stirred, and this was used as bait in a plastic cup (top diameter 6 cm, bottom inner diameter 4.6 cm).
20 2-day-old mixed-strain housefly larvae were released into the chambers (inner height: 4 cm), kept at 26°C ± 1°C, and the emergence rate of adults was examined. The emergence rate was defined as the emergence inhibition rate.
試験は1区2連制で行い結果を平均値で示した。The test was conducted in two consecutive sessions in one section, and the results are shown as an average value.
尚、期待値は、各々の単剤に対する供試昆虫の感受性の
間に全く相関がなく、両者の間に非依存的な連合作用し
かない場合には、a + b混合剤から期待される羽化
阻害率Pmは次式から求めた[B115s、 C,1,
、Ann、Appl、Biol、、 26.585(1
939)]。Note that the expected value is the eclosion expected from the a + b mixture when there is no correlation at all between the susceptibilities of the test insects to each single agent and there is only an independent combined effect between the two. The inhibition rate Pm was calculated from the following formula [B115s, C,1,
, Ann, Appl, Biol, 26.585 (1
939)].
Pm=’P a +P b (1−P a)但し、Pa
は、a剤のみによる実測阻害率、pbは、b剤のみによ
る実測阻害率を示し、下表では、Pmを百分率(%)で
示した。Pm='P a +P b (1-P a) However, Pa
indicates the actually measured inhibition rate by agent A only, pb indicates the actually measured inhibition rate by agent B only, and in the table below, Pm is expressed as a percentage (%).
試験液中の
ビ フ゛ロ シフ ゛
0 (ppm)
0.2
0.4
0.8
試験液中のイソブロチオラン濃度と
エバエ ・・コ は
値)
28[17]
55[32]
100[47]
100[47コ
100[56]
100[66]
20 m
59(%)
100[66]
100[72]
100[78]
ジ−クライト(製紙用)[ジ−クライト化学鉱業(KK
)]64.44%を混合粉砕して作ったキャリヤー73
部に対し、1,3−ジチオラン−2−イリデンマロン酸
ジメジメチルエステル25部リプロキシフェン2部を混
合して水和剤を調製した。Bifluorescence concentration in the test solution (ppm) 0.2 0.4 0.8 The concentration of isobrothiolane in the test solution and the E. co. [47 pieces 100 [56] 100 [66] 20 m 59 (%) 100 [66] 100 [72] 100 [78] Zikrite (for paper making) [Zikrite Chemical Mining (KK
)] Carrier 73 made by mixing and pulverizing 64.44%
25 parts of 1,3-dithiolane-2-ylidenemalonic acid dimedimethyl ester and 2 parts of liproxifen were mixed to prepare a wettable powder.
この水和剤を水で500倍に希釈し、ハエの発生してい
る堆肥の上に1平方メートル当り4リツトルかけたとこ
ろ、ハエの発生を約1カ月防ぐことができた。When this wettable powder was diluted 500 times with water and applied at 4 liters per square meter of compost where flies were infested, it was possible to prevent flies from appearing for about a month.
上表から明らかな通り、本発明の殺虫組成物は各単剤か
ら予想される期待値よりはるかに優れた効果を示した。As is clear from the above table, the insecticidal composition of the present invention exhibited effects far superior to the expected values expected from each single agent.
実部j引&
ネオゲンパウダー[第一工業製薬(KK)]55.56
%ゴーセノール[日本合成化学工業(KK)12.22
%、カープレックス#80[ジオツギ製薬(KK)]5
.5圀、ラジオ−z’ ト#200[昭和化学工業(K
K)122.22%、実施性y
実施例2と同じキャリヤー79部、1,3−ジチオラン
−2−イリデンマロン酸 ジエチルエステル20部とビ
リプロキシフェン1部を混合して水和剤を調製し、この
水和剤を水で500倍に希釈し、ハエの発生の激しい鶏
糞堆積物の上に1平方メートル当り5リツトルかけたと
ころ、ハエの発生を20日以上抑制できた。Real part j pull & neogen powder [Daiichi Kogyo Seiyaku (KK)] 55.56
% Gohsenol [Nippon Gohsei (KK) 12.22
%, Carplex #80 [Giotsugi Pharmaceutical (KK)] 5
.. 5, Radio-z'#200 [Showa Chemical Industry (K
K) 122.22%, practicality y 79 parts of the same carrier as in Example 2, 20 parts of 1,3-dithiolan-2-ylidenemalonic acid diethyl ester and 1 part of biliproxyfen were mixed to prepare a wettable powder, When this wettable powder was diluted 500 times with water and applied at 5 liters per square meter of chicken manure deposits where flies were heavily infested, the infestation of flies was suppressed for over 20 days.
Claims (1)
ピリジルオキシ)プロパンと、1,3−ジチオラン−2
−イリデンマロン酸のジエステルとを含有する殺虫組成
物。 (2)請求項1記載の1,3−ジチオラン−2−イリデ
ンマロン酸のジエステルが、低級アルキルエステル、低
級アルケニルエステル、又はベンジルエステルである殺
虫組成物。(3)請求項2記載の低級アルキルエステル
が、イソプロピルエステルである殺虫組成物。 (4)請求項1記載の殺虫組成物が殺うじ用途である殺
虫組成物。[Claims] (1) 1-(4-phenoxyphenoxy)-2-(2-
pyridyloxy)propane and 1,3-dithiolane-2
- an insecticidal composition containing a diester of ylidenemalonic acid. (2) An insecticidal composition, wherein the diester of 1,3-dithiolane-2-ylidenemalonic acid according to claim 1 is a lower alkyl ester, a lower alkenyl ester, or a benzyl ester. (3) An insecticidal composition in which the lower alkyl ester according to claim 2 is an isopropyl ester. (4) An insecticidal composition according to claim 1, which is used for killing maggots.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63208843A JPH0259502A (en) | 1988-08-23 | 1988-08-23 | Insecticidal composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63208843A JPH0259502A (en) | 1988-08-23 | 1988-08-23 | Insecticidal composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0259502A true JPH0259502A (en) | 1990-02-28 |
Family
ID=16563022
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP63208843A Pending JPH0259502A (en) | 1988-08-23 | 1988-08-23 | Insecticidal composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0259502A (en) |
-
1988
- 1988-08-23 JP JP63208843A patent/JPH0259502A/en active Pending
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