JPH01301603A - Insecticidal composition - Google Patents
Insecticidal compositionInfo
- Publication number
- JPH01301603A JPH01301603A JP63132399A JP13239988A JPH01301603A JP H01301603 A JPH01301603 A JP H01301603A JP 63132399 A JP63132399 A JP 63132399A JP 13239988 A JP13239988 A JP 13239988A JP H01301603 A JPH01301603 A JP H01301603A
- Authority
- JP
- Japan
- Prior art keywords
- ester
- insecticidal composition
- dithiolane
- difluorobenzoyl
- chlorophenyl
- 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 22
- 230000000749 insecticidal effect Effects 0.000 title claims abstract description 14
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- -1 1,3-dithiolane-2-indenemalonic acid diester Chemical class 0.000 claims abstract 8
- 150000005690 diesters Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000004480 active ingredient Substances 0.000 abstract description 5
- 239000000843 powder Substances 0.000 abstract description 4
- 238000009472 formulation Methods 0.000 abstract description 3
- 239000012752 auxiliary agent Substances 0.000 abstract description 2
- 239000000839 emulsion Substances 0.000 abstract description 2
- 239000008187 granular material Substances 0.000 abstract description 2
- 239000004615 ingredient Substances 0.000 abstract 2
- 239000000428 dust Substances 0.000 abstract 1
- 230000009969 flowable effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 13
- 241000238631 Hexapoda Species 0.000 description 9
- 241000255925 Diptera Species 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 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 description 3
- 239000005893 Diflubenzuron Substances 0.000 description 3
- 229940019503 diflubenzuron Drugs 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 230000032669 eclosion Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- 241001465754 Metazoa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 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
- 230000001419 dependent effect 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
- QEOQJCDTDKSLCS-UHFFFAOYSA-N dimethyl 2-(1,3-dithiolan-2-ylidene)propanedioate Chemical compound COC(=O)C(C(=O)OC)=C1SCCS1 QEOQJCDTDKSLCS-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 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
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PPOSFCNLNROPTA-UHFFFAOYSA-N n-carbamoyl-2,6-difluorobenzamide Chemical compound NC(=O)NC(=O)C1=C(F)C=CC=C1F PPOSFCNLNROPTA-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 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
- 238000003756 stirring Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000004563 wettable powder 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】
この発明は、1−(4−クロロフェニル)−3−(2,
6−ジフルオロベンゾイル)ウレアと、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 This invention provides 1-(4-chlorophenyl)-3-(2,
The present invention relates to an insecticidal composition containing 6-difluorobenzoyl)urea and a diester of 1,3-dithiolane-2-ylidenemalonic acid.
近年、有機リン酸エステル系、カーバメート系、ピレス
ロイド系等の梅々の殺虫剤に対して抵抗性を示す有害虫
の出現が問題とされており、それらの的確な駆除が課題
となっている。このことは、農業分野にとどまらず、ハ
エや蚊のような衛生害虫でもあてはまり、特に各種薬剤
に対して抵抗性を獲得したノ・工の駆除は困難である。In recent years, the emergence of harmful insects that are resistant to insecticides such as organic phosphate esters, carbamates, and pyrethroid insecticides has become a problem, and their accurate extermination has become an issue. This applies not only to the agricultural field, but also to sanitary pests such as flies and mosquitoes, and it is particularly difficult to exterminate insects that have acquired resistance to various chemicals.
一般に、抵抗性と感受性の有害虫は混合状態で棲息して
いるが、本発明者等は、抵抗性の度合いにかかわらず、
有害虫を的Jotに防除しうる方法を検討したところ、
1−(4−クロロフェニル) 、 3− (2,6−ジ
フルオロベンゾイル)ウレアと、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K
よシ、有害虫、ことにハエの幼虫を極めて効率的に防除
できることを見出した。In general, a mixture of resistant and susceptible harmful insects exists, but the present inventors believe that regardless of the degree of resistance,
After considering methods to target harmful insects, we found that
1-(4-chlorophenyl), 3-(2,6-difluorobenzoyl)urea, and 1,3-dithiolane-
Combined use with diester of 2-ylidenemalonic acid K
We have discovered that this method can extremely efficiently control insects, harmful insects, and especially fly larvae.
本発明の殺虫組成物の一方の有効成分である1−(4−
クロロフェニル) −3−(2,6−ジフルオロベンゾ
イル)ウレア(以下ジフルベンズロンと称する)は昆虫
の脱皮阻害剤として公知であり、防疫分野でも使用され
ているが、近年、これに対する抵抗性害虫が認められて
いる。1-(4-
Chlorophenyl)-3-(2,6-difluorobenzoyl)urea (hereinafter referred to as diflubenzuron) is known as an insect molting inhibitor and is also used in the field of epidemic prevention, but in recent years, insects that are resistant to it have been recognized. ing.
本発明の他方の有効成分である1、3−ジチオラン−2
−イ+)デンマロン酸のジエステル類も害虫防止剤とし
て特公昭52−4609号に公知である。1,3-dithiolane-2 which is the other active ingredient of the present invention
-i+) Diesters of denmalonic acid are also known as pest control agents in Japanese Patent Publication No. 4609/1983.
本発明の殺虫組成物は、下記の実施例に示されるとおシ
、各々の単剤から予期しえない優れた相乗的殺虫効果を
示す。The insecticidal composition of the present invention exhibits an excellent synergistic insecticidal effect that was unexpected from each single agent, as shown in the examples below.
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、たとえば低級アルキルエステル、低級アル
ケニルエステルおよびベンジルエステル等をあげること
ができる。低級アルキルエステルとしては、たとえばメ
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01−4アルキルエステルが、また低級アル
ケニルエステルとしては、たとえばアリル、メチルアリ
ル等のC2−4アルケニルエステルをあげることができ
る。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、同種のジ低級アルギルエステルの場合がさら
に好適であり、そして最も好適なものはノイソプロビル
エステル(以下インブロチオランと称する)である。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 01-4 alkyl esters such as methyl, ethyl, propyl, isopropyl, butyl, and isobutyl, and examples of lower alkenyl esters include C2-4 alkenyl esters such as allyl and methylallyl. . 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 the same type, even more preferable that they are the same type of di-lower argyl ester, and most preferably A preferred one is noisoprobyl ester (hereinafter referred to as inbrothiolane).
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および/捷たは補助剤と混合す
ることにより、この分野で慣用の剤型、たとえば水利剤
、ドライフロアゾル製剤、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 a suitable carrier and/or auxiliary agent according to a conventional method, so that the insecticidal composition can be prepared into a dosage form customary in this field, such as a water use agent, a dry fur sol, etc. It can be prepared into formulations, 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、ノフルペンズ
ロンの方が少量であり、ノペンズフルロン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30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 amount of noflupenzuron is smaller, and the diester of 1,3-dithiolan-2-ylidenemalonic acid is about 1 part to 30 parts per 1 part of noflupenzuron.
本発明の目的を達成するには、上述のように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 containing two types of active ingredients at the same time 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、こと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, especially 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 by way of Examples.
実施例1
小麦ふす′=f1部、実峡動物用粉末飼料(船橋農4x
K)1部の混合物に対し、同重量の水にイソブロチオラ
ン10係水和剤とジンルペンズロン10%水利剤を適宜
混合分散させた希釈液を加えて攪拌し、それを餌として
プラスチック製カップ(上内径6cnL、JjE内径4
,6儂、内高4crrL)に入れ、イエバエ(混合系統
)の2日令幼虫を20頭放し、26℃±1℃に保って成
虫への羽化率を調べ、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。Example 1 Wheat bran = f1 part, Jikyo animal powder feed (Funabashi Agriculture 4x
K) To 1 part of the mixture, add a diluted solution prepared by appropriately mixing and dispersing isobrothiolane 10 hydrating powder and Zinlupenzuron 10% water conservancy in the same weight of water, stir, and use it as bait in a plastic cup ( Upper inner diameter 6cnL, JjE inner diameter 4
20 2-day-old house fly (mixed strain) larvae were released into a 2-day-old housefly (mixed strain) and kept at 26°C ± 1°C to examine the rate of emergence into adults, and the rate was corrected by the rate of emergence in the control group. The non-eclosion rate was defined as the eclosion inhibition rate.
試験は1区2連制でおこガわれ、その結果を次表に示す
。The test was held in two consecutive sections, and the results are shown in the table below.
ズロン濃度 0 5 10
20 ppmOppmo 0 8
23 係0.5 41 64(4
1) 87(46) 100(55)1.0
69 97(69) 100(71)
100(76)2.0 79 100(
79) Zoo(81) 100(88)*期
待値二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、a+b混合剤から期待される羽化阻害率Pmは次の
式から求められる。〔B115s、 C,1,(193
9) Ann。Zuron concentration 0 5 10
20 ppmOppmo 0 8
23 Section 0.5 41 64 (4
1) 87 (46) 100 (55) 1.0
69 97 (69) 100 (71)
100 (76) 2.0 79 100 (
79) Zoo (81) 100 (88) *Expected value 2 If there is no correlation between the susceptibility of the test insects to each single agent, and there is only a non-dependent association effect between the two, then from the a + b mixture The expected emergence inhibition rate Pm is calculated from the following formula. [B115s, C,1, (193
9) Ann.
Appl、 Eiol、 、 26 、585 )Pm
=Pa+Pb (1−Pa )
ただし、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。Pmは混合剤の阻害率(%)を
示す。Appl, Eiol, 26, 585) Pm
=Pa+Pb (1-Pa) However, Pa is the actually measured inhibition rate by only agent A, and Pb is the actually measured inhibition rate by only agent b. Pm indicates the inhibition rate (%) of the mixture.
上表から明らかなとお夛、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.
実施例2
ネオゲン・ξウダー(第一工業製薬KK)5.56%、
ゴーセノール(日本合成化学工業KX ) 2.224
.カープレックス+80(ジオツギ製薬■α)5.56
%、ラジオライ)+200(昭和化学工業KK)22.
221、ジ−クライト(製紙用、ジ−クライト化学鉱業
KK)64.4.41を混合粉砕して作ったキャリヤー
78部に対し、ジフルベンズロン2mと1.3−ジチオ
ラン−2−イリデンマロン酸ジメチルエステル20部を
混合して水利剤を調製した。Example 2 Neogen ξ Uda (Daiichi Kogyo Seiyaku KK) 5.56%,
Gohsenol (Nippon Gosei KX) 2.224
.. Carplex +80 (Giotsugi Pharmaceutical ■α) 5.56
%, Radioly) +200 (Showa Kagaku Kogyo KK) 22.
221, Diflubenzuron 2m and 1,3-dithiolan-2-ylidenemalonic acid dimethyl ester 20% to 78 parts of a carrier made by mixing and pulverizing 64.4.41 of Zikrite (for paper making, Zikrite Chemical Mining KK). An irrigation agent was prepared by mixing the two parts.
この水和剤を水で500倍に希釈し、ノ・工の発生して
いる鶏ふんの堆積の上に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カ月防いだ。When this wettable powder was diluted 500 times with water and applied at 4 liters per square meter on the piles of chicken feces that were causing flies, it prevented the growth of flies for about a month.
実施例3
実施例1と同じキャリヤー74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25部および
ジフルベンズロン1部を混合して水利剤を調製し、この
水和剤を水で500倍に希釈し、ハエの発生している堆
肥の上から1平方メートル当シ4リットルかけたところ
、ハエの発生を約1カ月抑制できた。Example 3 A hydrating agent was prepared by mixing 74 parts of the same carrier as in Example 1, 25 parts of 1,3-dithiolane-2-ylidenemalonic acid diethyl ester, and 1 part of diflubenzuron, and the hydrating agent was diluted 500 times with water. When diluted and poured 4 liters per square meter of compost where flies were infested, it was able to suppress the fly infestation for about a month.
Claims (4)
フルオロベンゾイル)ウレアと、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。(1) 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea and 1,3-dithiolane-
An insecticidal composition containing a diester of 2-ylidenemalonic acid.
ルエステルまたはベンジルエステルである請求項1に記
載の殺虫組成物。(2) The insecticidal composition according to claim 1, wherein the ester is a lower alkyl ester, a lower alkenyl ester, or a benzyl ester.
ある請求項2に記載の殺虫組成物。(3) The insecticidal composition according to claim 2, wherein the lower alkyl ester is an isopropyl ester.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63132399A JPH01301603A (en) | 1988-05-30 | 1988-05-30 | Insecticidal composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63132399A JPH01301603A (en) | 1988-05-30 | 1988-05-30 | Insecticidal composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH01301603A true JPH01301603A (en) | 1989-12-05 |
Family
ID=15080484
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP63132399A Pending JPH01301603A (en) | 1988-05-30 | 1988-05-30 | Insecticidal composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH01301603A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20020062570A (en) * | 2001-01-22 | 2002-07-26 | 다케다 야쿠힌 고교 가부시키가이샤 | Method of application of agricultural chemicals and agricultural chemical preparation used therefor |
-
1988
- 1988-05-30 JP JP63132399A patent/JPH01301603A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20020062570A (en) * | 2001-01-22 | 2002-07-26 | 다케다 야쿠힌 고교 가부시키가이샤 | Method of application of agricultural chemicals and agricultural chemical preparation used therefor |
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