JP6618364B2 - Ester compounds and uses thereof - Google Patents
Ester compounds and uses thereof Download PDFInfo
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- JP6618364B2 JP6618364B2 JP2016000112A JP2016000112A JP6618364B2 JP 6618364 B2 JP6618364 B2 JP 6618364B2 JP 2016000112 A JP2016000112 A JP 2016000112A JP 2016000112 A JP2016000112 A JP 2016000112A JP 6618364 B2 JP6618364 B2 JP 6618364B2
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- -1 Ester compounds Chemical class 0.000 title claims description 86
- 239000003795 chemical substances by application Substances 0.000 claims description 52
- 241000607479 Yersinia pestis Species 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 87
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 125000001424 substituent group Chemical group 0.000 description 31
- 239000000203 mixture Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 238000009472 formulation Methods 0.000 description 20
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- 239000004014 plasticizer Substances 0.000 description 1
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- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
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- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
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- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
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Landscapes
- Catching Or Destruction (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、エステル化合物、並びにこれを用いた害虫防除剤及び害虫方法に関するものである。 The present invention relates to an ester compound, a pest control agent and a pest method using the ester compound.
従来、有害生物を防除するために種々の化合物が合成されている(非特許文献1参照)。また、特許文献1及び2には、ある種のエステル化合物が開示されている。しかしながら、これら開示の有害生物成分の防除効力は必ずしも満足のいくものではない。 Conventionally, various compounds have been synthesized in order to control pests (see Non-Patent Document 1). Patent Documents 1 and 2 disclose certain ester compounds. However, the control efficacy of these disclosed pest components is not always satisfactory.
本発明は、優れた有害生物防除効力を有する新規エステル化合物を提供することを課題とする。 An object of the present invention is to provide a novel ester compound having an excellent pest control effect.
本発明者らは、鋭意検討を行った結果、下記一般式[化1]で示されるエステル化合物が優れた有害生物防除効力を有することを見出し、本発明を完成するに至った。 As a result of intensive studies, the present inventors have found that an ester compound represented by the following general formula [Chemical Formula 1] has an excellent pest control effect, and has completed the present invention.
即ち、本発明は、以下の発明に係るものである。
(1)一般式[化1]
(2)前記一般式[化1]において、R2がメチル基である(1)に記載のエステル化合物。
(3)前記一般式[化1]において、R3がメチル基である(2)に記載のエステル化合物。
(4)前記一般式[化1]において、R1がメトキシメチル基、メチル基、エチニル基または水素原子である(2)又は(3)に記載のエステル化合物。
(5)前記一般式[化1]においてR2がメチル基、R3がメチル基であり、R1がメトキシメチル基、メチル基、または水素原子である(1)に記載のエステル化合物。
(6)前記一般式[化1]において、R1がエチニル基であり、R2が水素原子であり、R3がメチル基である(1)に記載のエステル化合物。
(7)(1)ないし(6)のいずれか1に記載のエステル化合物を有効成分として含有する有害生物防除剤。
(8)(1)ないし(6)のいずれか1に記載のエステル化合物を有害生物又は有害生物の生息場所に施用する有害生物の防除方法。
That is, the present invention relates to the following inventions.
(1) General formula [Formula 1]
(2) The ester compound according to (1), wherein in the general formula [Chemical Formula 1], R 2 is a methyl group.
(3) The ester compound according to (2), wherein in the general formula [Chemical Formula 1], R 3 is a methyl group.
(4) The ester compound according to (2) or (3), wherein, in the general formula [Chemical Formula 1], R 1 is a methoxymethyl group, a methyl group, an ethynyl group, or a hydrogen atom.
(5) The ester compound according to (1), wherein in the general formula [Chemical Formula 1], R 2 is a methyl group, R 3 is a methyl group, and R 1 is a methoxymethyl group, a methyl group, or a hydrogen atom.
(6) The ester compound according to (1), wherein, in the general formula [Chemical Formula 1], R 1 is an ethynyl group, R 2 is a hydrogen atom, and R 3 is a methyl group.
(7) A pest control agent comprising the ester compound according to any one of (1) to (6) as an active ingredient.
(8) A method for controlling pests, wherein the ester compound according to any one of (1) to (6) is applied to pests or pest habitats.
本発明化合物は優れた有害生物防除効力を有することから、有害生物防除剤の有効成分として有用である。 Since the compound of the present invention has an excellent pest control effect, it is useful as an active ingredient of a pest control agent.
本発明化合物には、シクロプロパン環上の1位および3位に存在する2個の不斉炭素原子に由来する光学異性体、並びに、シクロプロパン環3位の置換基に存在する1’位の二重結合に由来する異性体が存在するが、本発明には有害生物防除活性を有する各異性体および任意の比率の異性体混合物が含まれる。 The compound of the present invention includes an optical isomer derived from two asymmetric carbon atoms present at the 1-position and the 3-position on the cyclopropane ring, and a 1'-position present on a substituent at the 3-position of the cyclopropane ring. Although isomers derived from double bonds exist, the present invention includes isomers having pesticidal activity and isomer mixtures in any ratio.
本発明化合物の形態としては以下のものが含まれる。
一般式[化2]
シクロプロパン環1位の絶対立体配置がR配置である化合物;
シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置である化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がシス配置である化合物;
シクロプロパン環3位の置換基に存在する1’位の二重結合の相対配置がE配置である化合物;
シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置であり、シクロプロパン環3位の置換基に存在する1’位の二重結合の相対配置がE配置である化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置である化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置であり、シクロプロパン環3位の置換基に存在する1’位の二重結合の相対配置がE配置である化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がシス配置であり、シクロプロパン環3位の置換基に存在する1’位の二重結合の相対配置がE配置である化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置であり、シクロプロパン環3位の置換基に存在する1’位の二重結合の相対配置がZ配置である化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がシス配置であり、シクロプロパン環3位の置換基に存在する1’位の二重結合の相対配置がZ配置である化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置であるものに富む化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置であるものが80%以上である化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置であるものが90%以上である化合物。
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がシス配置であるものに富む化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がシス配置であるものが80%以上である化合物;
シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がシス配置であるものが90%以上である化合物。
Examples of the form of the compound of the present invention include the following.
[Formula 2]
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration;
A compound wherein the relative configuration of the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration;
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the relative configuration of the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a cis configuration;
A compound in which the relative configuration of the 1'-position double bond present in the substituent at the 3-position of the cyclopropane ring is the E configuration;
The relative configuration of the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration, and the relative configuration of the 1'-position double bond present in the substituent at the 3-position of the cyclopropane ring is A compound in the E configuration;
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration;
The absolute configuration at the 1-position of the cyclopropane ring is the R configuration, the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is the trans configuration, and the substitution at the 3-position of the cyclopropane ring is A compound in which the relative configuration of the 1'-position double bond present in the group is the E configuration;
The absolute configuration at the 1-position of the cyclopropane ring is the R configuration, the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a cis configuration, and the substitution at the 3-position of the cyclopropane ring is A compound in which the relative configuration of the 1'-position double bond present in the group is the E configuration;
The absolute configuration at the 1-position of the cyclopropane ring is the R configuration, the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is the trans configuration, and the substitution at the 3-position of the cyclopropane ring is A compound in which the relative configuration of the 1'-position double bond present in the group is the Z configuration;
The absolute configuration at the 1-position of the cyclopropane ring is the R configuration, the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a cis configuration, and the substitution at the 3-position of the cyclopropane ring is A compound in which the relative configuration of the 1'-position double bond present in the group is the Z configuration;
A compound rich in that the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration;
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is 80% or more. ;
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is R-configuration, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is 90% or more .
A compound rich in those in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a cis configuration;
Compounds in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is 80% or more ;
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is 90% or more. .
次に本発明化合物の製造法について説明する。
本発明化合物は、通常のエステル化合物を製造する方法であれば、特に限定されるものではないが、例えば以下に示す方法により製造することができる。
(製造法1)
式[化3]
式[化4]
Although this invention compound will not be specifically limited if it is a method of manufacturing a normal ester compound, For example, it can manufacture by the method shown below.
(Production method 1)
Formula [Chemical Formula 3]
該反応性誘導体としては、[化4]で示されるカルボン酸化合物の酸ハロゲン化物、該カルボン酸化合物の酸無水物および該カルボン酸化合物のエステル等が挙げられる。該酸ハロゲン化物としては、酸クロライド化合物が挙げられ、エステルとしてはメチルエステル、エチルエステルなどが挙げられる。
該反応は、通常、縮合剤又は塩基の存在下、溶媒中で行なわれる。
縮合剤としては、例えば、ジシクロヘキシルカルボジイミド、1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライドが挙げられ、また、
塩基としては、トリエチルアミン、ピリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン等の有機塩基が挙げられる。
溶媒としては、例えばトルエン及びヘキサン等の炭化水素、テトラヒドロフラン等のエ−テル、エチルアセテートなどのエステル、並びに、クロロベンゼン等のハロゲン化炭化水素、及びこれらの混合溶媒等が挙げられる。
Examples of the reactive derivative include an acid halide of the carboxylic acid compound represented by [Chemical Formula 4], an acid anhydride of the carboxylic acid compound, and an ester of the carboxylic acid compound. Examples of the acid halide include acid chloride compounds, and examples of the ester include methyl ester and ethyl ester.
The reaction is usually performed in a solvent in the presence of a condensing agent or a base.
Examples of the condensing agent include dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride,
Examples of the base include organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine, diisopropylethylamine.
Examples of the solvent include hydrocarbons such as toluene and hexane, ethers such as tetrahydrofuran, esters such as ethyl acetate, halogenated hydrocarbons such as chlorobenzene, and mixed solvents thereof.
該反応において、式[化3]で示されるアルコ−ル化合物と、式[化4]で示されるカルボン酸化合物又はその反応性誘導体の使用モル比は任意に設定できるが、好ましくは、等モル又はそれに近い比である。
縮合剤又は塩基は、式[化3]で示されるアルコ−ル化合物1モルに対して、通常は0.25モルから過剰量まで任意の割合で使用することができ、好ましくは0.5モル〜2モルである。これらの縮合剤又は塩基は、式[化4]で示されるカルボン酸化合物又はその反応性誘導体の種類により適宜選択される。
反応終了後の反応混合物は、これを濾過して濾液を濃縮する、又は、これを水に注加した後に有機溶媒抽出、濃縮する等の通常の後処理操作を施すことにより、本発明化合物を得ることができる。得られた本発明化合物はクロマトグラフィ−、蒸留等の操作によって精製することができる。
In the reaction, the molar ratio of the alcohol compound represented by the formula [Chemical Formula 3] and the carboxylic acid compound represented by the formula [Chemical Formula 4] or a reactive derivative thereof can be set arbitrarily, but preferably equimolar Or a ratio close to that.
The condensing agent or base can be used in an arbitrary ratio from 0.25 mol to an excess amount with respect to 1 mol of the alcohol compound represented by the formula [Chemical Formula 3], preferably 0.5 mol. ~ 2 moles. These condensing agents or bases are appropriately selected depending on the type of the carboxylic acid compound represented by the formula [Chemical Formula 4] or a reactive derivative thereof.
The reaction mixture after completion of the reaction is filtered to concentrate the filtrate, or poured into water and then subjected to usual post-treatment operations such as organic solvent extraction and concentration, whereby the compound of the present invention is obtained. Can be obtained. The obtained compound of the present invention can be purified by operations such as chromatography and distillation.
式[化3]で示される様々なアルコール化合物は公知化合物であり、該文献に記載の方法で製造することができる。4−エチニルテトラフルオロベンジルアルコールは特開昭64−66146号公報に示されたようにして製造することができる。 Various alcohol compounds represented by the formula [Chemical Formula 3] are known compounds and can be produced by the methods described in the literature. 4-Ethynyltetrafluorobenzyl alcohol can be produced as disclosed in JP-A No. 64-66146.
式[化4]で示されるカルボン酸化合物のうち、下記式[化5]で示されるカルボン酸は公知化合物であり、AGR.BIOL.CHEM.,vol.27,no,5,1963,pages373−378に記載の方法で製造することができる。他のカルボン酸化合物も同様の方法で製造することができる。
式[化5]
Formula [Chemical Formula 5]
本発明の有害生物防除剤は本発明化合物そのもののみ単独で用いることも可能であるが、下記のような製剤として使用することもできる。それら製剤としては、例えば、蚊取線香、蚊取マットや蚊取リキッドのような加熱蒸散剤、ファン式蚊取、油剤、乳剤、エアゾール剤、炭酸ガス製剤、水和剤、フロアブル剤(水中懸濁剤、水中乳濁剤等)、マイクロカプセル剤、粉剤、粒剤、錠剤、ピエゾ式殺虫製剤、加熱燻煙剤(自己燃焼型燻煙剤、化学反応型燻煙剤、多孔セラミック板燻煙剤等)、非加熱蒸散剤(樹脂蒸散剤、紙蒸散剤、不織布蒸散剤、編織物蒸散剤、昇華性錠剤等)、煙霧剤(フォッギング剤)、直接接触剤(シート状接触剤、テープ状接触剤、ネット状接触剤等)、ULV剤及び毒餌などが挙げられる。 The pest control agent of the present invention can be used alone as a compound of the present invention alone, but can also be used as a preparation as described below. These preparations include, for example, heat transpiration agents such as mosquito coils, mosquito mats and liquids, fan mosquito traps, oils, emulsions, aerosols, carbon dioxide preparations, wettable powders and flowables Suspensions, emulsions in water, etc.), microcapsules, powders, granules, tablets, piezo insecticides, heated smoke (self-burning smoke, chemical reaction smoke, porous ceramic plate smoke) Agent), non-heated transpiration agent (resin transpiration agent, paper transpiration agent, non-woven fabric transpiration agent, knitted fabric transpiration agent, sublimation tablet, etc.), fumes (fogging agent), direct contact agent (sheet-like contact agent, tape form) Contact agents, net-like contact agents, etc.), ULV agents and poison baits.
製剤化の方法としては、例えば以下の方法を挙げることができる。
(1)本発明化合物を、固体担体、液体担体、ガス状担体、餌等と混合し、必要に応じて界面活性剤その他の製剤用補助剤を添加・加工する方法。
(2)本発明化合物を、有効成分を含有していない基材に含浸する方法。
(3)本発明化合物及び基材を混合した後に成形加工する方法。
これらの製剤には、製剤形態にもよるが、通常、本発明化合物を重量比で0.001〜98%含有する。
Examples of the formulation method include the following methods.
(1) A method in which the compound of the present invention is mixed with a solid carrier, liquid carrier, gaseous carrier, bait and the like, and a surfactant and other formulation adjuvants are added and processed as necessary.
(2) A method of impregnating a base material containing no active ingredient with the compound of the present invention.
(3) A method of molding after mixing the compound of the present invention and the substrate.
These preparations usually contain 0.001 to 98% by weight of the compound of the present invention, depending on the form of preparation.
製剤化の際に用いられる固体担体としては、例えば粘土類(カオリンクレー、珪藻土、ベントナイト、フバサミクレー、酸性白土等)、合成含水酸化珪素、タルク、セラミック、その他の無機鉱物(セリサイト、活性炭、炭酸カルシウム、シリカ等)等の微粉末及び粒状物、常温で固体の物質(2,4,6−トリイソプロピル−1,3,5−トリオキサン、ナフタリン、p−ジクロロベンゼン、樟脳、アダマンタン等)、並びに羊毛、絹、綿、麻、パルプ、合成樹脂(例えば、低密度ポリエチレン、直鎖状低密度ポリエチレン、高密度ポリエチレン等のポリエチレン系樹脂;エチレン−酢酸ビニル共重合体等のエチレン−ビニルエステル共重合体;エチレン−メタクリル酸メチル共重合体、エチレン−メタクリル酸エチル共重合体等のエチレン−メタクリル酸エステル共重合体;エチレン−アクリル酸メチル共重合体、エチレン−アクリル酸エチル共重合体等のエチレン−アクリル酸エステル共重合体;エチレン−アクリル酸共重合体等のエチレン−ビニルカルボン酸共重合体;ポリプロピレン、プロピレン−エチレン共重合体等のポリプロピレン系樹脂;ポリ−4−メチルペンテン−1、ポリブテン−1、ポリブタジエン、ポリスチレン;アクリロニトリル−スチレン樹脂;アクリロニトリル−ブタジエン−スチレン樹脂、スチレン−共役ジエンブロック共重合体、スチレン−共役ジエンブロック共重合体水素添加物等のスチレン系エラストマー;フッ素樹脂;ポリメタクリル酸メチル等のアクリル系樹脂;ナイロン6、ナイロン66等のポリアミド系樹脂;ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンテレフタレエート等のポリエステル系樹脂;ポリカーボネート、ポリアセタール、ポリアリレート、ヒドロキシ安息香酸ポリエステル、ポリエーテルイミド、ポリエステルカーボネート、ポリフェニレンエーテル樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリウレタン、発泡ポリウレタン、発泡ポリプロピレン、発泡エチレン等の多孔質樹脂)、ガラス、金属、セラミック等の1種または2種以上からなるフェルト、繊維、布、編物、シート、紙、糸、発泡体、多孔質体及びマルチフィラメントが挙げられる。 Examples of solid carriers used in the formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramic, and other inorganic minerals (sericite, activated carbon, carbonic acid). Fine powders and granules such as calcium, silica, etc., solid substances at room temperature (2,4,6-triisopropyl-1,3,5-trioxane, naphthalene, p-dichlorobenzene, camphor, adamantane, etc.), and Wool, silk, cotton, hemp, pulp, synthetic resin (eg, polyethylene resins such as low density polyethylene, linear low density polyethylene, and high density polyethylene; ethylene-vinyl ester copolymer such as ethylene-vinyl acetate copolymer) Polymer; Ethylene such as ethylene-methyl methacrylate copolymer, ethylene-ethyl methacrylate copolymer -Methacrylic acid ester copolymer; Ethylene-acrylic acid ester copolymer such as ethylene-methyl acrylate copolymer and ethylene-ethyl acrylate copolymer; Ethylene-vinyl carboxylic acid such as ethylene-acrylic acid copolymer Copolymer; Polypropylene resin such as polypropylene and propylene-ethylene copolymer; poly-4-methylpentene-1, polybutene-1, polybutadiene, polystyrene; acrylonitrile-styrene resin; acrylonitrile-butadiene-styrene resin, styrene-conjugate Styrene elastomers such as diene block copolymers and hydrogenated styrene-conjugated diene block copolymers; fluororesins; acrylic resins such as polymethyl methacrylate; polyamide resins such as nylon 6 and nylon 66; Polyester resins such as rate, polyethylene naphthalate, polybutylene terephthalate; polycarbonate, polyacetal, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, polyurethane, Felt, fiber, cloth, knitted fabric, sheet, paper, thread, foam, porous body made of one or more of foamed polyurethane, foamed polypropylene, foamed ethylene, etc.), glass, metal, ceramic, etc. And multifilaments.
液体担体としては、例えば芳香族または脂肪族炭化水素類(キシレン、アルキルナフタレン、フェニルキシリルエタン、ケロシン、軽油、ヘキサン、シクロヘキサン等)、アルコール類(メタノール、エタノール、イソプロピルアルコール、ブタノール、ヘキサノール、ベンジルアルコール、エチレングリコール等)、エーテル類(ジエチルエーテル、エチレングリコールジメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、テトラヒドロフラン等)、エステル類(酢酸エチル、酢酸ブチル等)、ケトン類(アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等)、ニトリル類(アセトニトリル、イソブチロニトリル等)、スルホキシド類(ジメチルスルホキシド等)、酸アミド類(N,N−ジメチルホルムアミド、N−メチル−ピロリドン等)、炭酸アルキリデン類(炭酸プロピレン等)、植物油(大豆油、綿実油等)、植物精油(オレンジ油、ヒソップ油、レモン油等)、及び水が挙げられる。 Examples of the liquid carrier include aromatic or aliphatic hydrocarbons (xylene, alkylnaphthalene, phenylxylylethane, kerosene, light oil, hexane, cyclohexane, etc.), alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl). Alcohol, ethylene glycol, etc.), ethers (diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, tetrahydrofuran, etc.), esters (ethyl acetate, butyl acetate, etc.), ketones (acetone) , Methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), nitriles (acetonitrile, isobutyronitrile) ), Sulfoxides (dimethyl sulfoxide, etc.), acid amides (N, N-dimethylformamide, N-methyl-pyrrolidone, etc.), alkylidene carbonates (propylene carbonate, etc.), vegetable oils (soybean oil, cottonseed oil, etc.), plant essential oils (Orange oil, hyssop oil, lemon oil, etc.) and water.
ガス状担体としては、例えばブタンガス、フロンガス、液化石油ガス(LPG)、ジメチルエーテル、及び炭酸ガス等の圧縮ガスが挙げられる。 Examples of the gaseous carrier include compressed gases such as butane gas, Freon gas, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide gas.
界面活性剤としては、例えばアルキル硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキルアリールエーテル類、アルキルアリールエーテル類のポリオキシエチレン化物、ポリエチレングリコールエーテル類、多価アルコールエステル類及び糖アルコール誘導体が挙げられる。 Surfactants include, for example, alkyl sulfate esters, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyarylethylenes of alkyl aryl ethers, polyethylene glycol ethers, polyhydric alcohol esters and sugars. Examples include alcohol derivatives.
その他の製剤用補助剤としては、固着剤、分散剤及び安定剤等、具体的には例えばカゼイン、ゼラチン、多糖類(でんぷん、アラビアガム、セルロース誘導体、アルギン酸等)、リグニン誘導体、ベントナイト、糖類、合成水溶性高分子(ポリビニルアルコール、ポリビニルピロリドン)、ポリアクリル酸等、BHT(2,6−ジ−tert−ブチル−4−メチルフェノール)、及びBHA(2−tert−ブチル−4−メトキシフェノールと3−tert−ブチル−4−メトキシフェノールとの混合物)が挙げられる。更に、必要に応じて着色剤や香料等が適宜配合されても構わない。 Other formulation adjuvants include sticking agents, dispersants and stabilizers, such as casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone), polyacrylic acid, etc., BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (2-tert-butyl-4-methoxyphenol) 3-tert-butyl-4-methoxyphenol). Furthermore, a coloring agent, a fragrance | flavor, etc. may be mix | blended suitably as needed.
蚊取線香の基材としては、例えば木粉、除虫菊抽出粕粉等の植物性粉末とタブ粉、澱粉、カルボキシメチルセルロース、グルテン等の結合剤との混合物が挙げられる。
蚊取マットの基材としては、例えばコットンリンターを板状に固めたもの、及びコットンリンターとパルプとの混合物のフィリブルを板状に固めたものが挙げられる。
自己燃焼型燻煙剤の基材としては、例えば、硝酸塩、亜硝酸塩、グアニジン塩、塩素酸カリウム、ニトロセルロース、エチルセルロース、木粉等の燃焼発熱剤、アルカリ金属塩、アルカリ土類金属塩の熱分解刺激剤、硝酸カリウム等の酸素供給剤、メラミン、小麦デンプン等の支燃剤、珪藻土等の増量剤及び合成糊料等の結合剤が挙げられる。
Examples of the base material of the mosquito coil include a mixture of a vegetable powder such as wood powder and pesticide extracted chrysanthemum powder and a binder such as tab powder, starch, carboxymethylcellulose, and gluten.
Examples of the base material of the mosquito trap include those obtained by solidifying a cotton linter into a plate shape and those obtained by solidifying a fillet of a mixture of cotton linter and pulp into a plate shape.
Examples of the base material for the self-burning smoke agent include nitrate, nitrite, guanidine salt, potassium chlorate, nitrocellulose, ethylcellulose, wood powder and other combustion exothermic agents, alkali metal salts, alkaline earth metal salt heat Examples include decomposition stimulants, oxygen supply agents such as potassium nitrate, flame retardants such as melamine and wheat starch, bulking agents such as diatomaceous earth, and binders such as synthetic pastes.
化学反応型燻煙剤の基材としては、例えば、アルカリ金属の硫化物、多硫化物、水硫化物、酸化カルシウム等の発熱剤、炭化鉄、活性白土等の触媒剤、アゾジカルボンアミド、ベンゼンスルホニルヒドラジド、ジニトロペンタメチレンテトラミン、ポリスチレン、ポリウレタン等の有機発泡剤、及び、天然繊維片、合成繊維片等の充填剤が挙げられる。 Examples of the base material for the chemical reaction type smoke agent include exothermic agents such as alkali metal sulfides, polysulfides, hydrosulfides, and calcium oxide, catalyst agents such as iron carbide and activated clay, azodicarbonamide, and benzene. Examples thereof include organic foaming agents such as sulfonyl hydrazide, dinitropentamethylenetetramine, polystyrene, and polyurethane, and fillers such as natural fiber pieces and synthetic fiber pieces.
樹脂蒸散剤等の基材に用いられる樹脂としては、例えば、低密度ポリエチレン、直鎖状低密度ポリエチレン、高密度ポリエチレン等のポリエチレン系樹脂;エチレン−酢酸ビニル共重合体等のエチレン−ビニルエステル共重合体;エチレン−メタクリル酸メチル共重合体、エチレン−メタクリル酸エチル共重合体等のエチレン−メタクリル酸エステル共重合体;エチレン−アクリル酸メチル共重合体、エチレン−アクリル酸エチル共重合体等のエチレン−アクリル酸エステル共重合体;エチレン−アクリル酸共重合体等のエチレン−ビニルカルボン酸共重合体;ポリプロピレン、プロピレン−エチレン共重合体等のポリプロピレン系樹脂;ポリ−4−メチルペンテン−1、ポリブテン−1、ポリブタジエン、ポリスチレン、アクリロニトリル−スチレン樹脂;アクリロニトリル−ブタジエン−スチレン樹脂、スチレン−共役ジエンブロック共重合体、スチレン−共役ジエンブロック共重合体水素添加物等のスチレン系エラストマー;フッ素樹脂;ポリメタクリル酸メチル等のアクリル酸樹脂;ナイロン6、ナイロン66等のポリアミド系樹脂;ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンフタレート等のポリエステル系樹脂;ポリカーボネート、ポリアセタール、ポリアリレート、ヒドロキシ安息香酸ポリエステル、ポリエーテルイミド、ポリエステルカーボネート、ポリフェニレンエーテル樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリウレタン等が挙げられ、これらの基材は、単独で用いても2種以上の混合物として用いても良く、これらの基材には必要によりフタル酸エステル類(フタル酸ジメチル、フタル酸ジオクチル等)、アジピン酸エステル類、ステアリン酸等の可塑剤が添加されていてもよい。樹脂蒸散剤は、本発明化合物を上記基材中に混練した後、射出成型、押出成型、プレス成型等により成型することにより得ることができる。得られた樹脂製剤は、必要により更に成型、裁断等の工程を経て、板状、フィルム状、テープ状、網状、ひも状等の形状に加工することもできる。これらの樹脂製剤は、例えば、非加熱蒸散剤、動物用首輪、動物用イヤータッグ、シート製剤、誘引テープ、誘引紐、園芸用支柱として加工される。 Examples of the resin used for the substrate such as a resin transpiration agent include polyethylene resins such as low density polyethylene, linear low density polyethylene, and high density polyethylene; and ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymer. Polymer; ethylene-methacrylic acid ester copolymer such as ethylene-methyl methacrylate copolymer and ethylene-ethyl methacrylate copolymer; ethylene-methyl acrylate copolymer, ethylene-ethyl acrylate copolymer, etc. Ethylene-acrylic acid ester copolymer; ethylene-vinyl carboxylic acid copolymer such as ethylene-acrylic acid copolymer; polypropylene resin such as polypropylene and propylene-ethylene copolymer; poly-4-methylpentene-1, Polybutene-1, polybutadiene, polystyrene, acrylonitrile Styrene resin; Styrenic elastomer such as acrylonitrile-butadiene-styrene resin, styrene-conjugated diene block copolymer, hydrogenated styrene-conjugated diene block copolymer; Fluororesin; Acrylic resin such as polymethyl methacrylate; Nylon 6, polyamide resins such as nylon 66; polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene phthalate; polycarbonate, polyacetal, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, poly Examples thereof include vinyl chloride, polyvinylidene chloride, polyurethane and the like. These substrates may be used alone or as a mixture of two or more. Phthalates necessary to (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters, plasticizers such as stearic acid may be added. The resin transpiration agent can be obtained by kneading the compound of the present invention in the above-mentioned base material and then molding it by injection molding, extrusion molding, press molding or the like. The obtained resin preparation can be further processed into a plate shape, a film shape, a tape shape, a net shape, a string shape or the like through steps such as molding and cutting if necessary. These resin preparations are processed, for example, as a non-heated transpiration agent, an animal collar, an animal ear tag, a sheet preparation, an attracting tape, an attracting string, and a garden support.
毒餌の基材としては、例えば、穀物粉、植物油、糖、結晶セルロース等の餌成分、BHT、ノルジヒドログアイアレチン酸等の酸化防止剤、デヒドロ酢酸等の保存料、トウガラシ粉末等の子どもやペットによる誤食防止剤、及びチーズ香料、タマネギ香料、ピーナッツオイル等の害虫誘引性香料があげられる。 Examples of poison bait bases include, for example, bait ingredients such as cereal flour, vegetable oil, sugar, crystalline cellulose, antioxidants such as BHT and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, children such as pepper powder, Examples include anti-fouling agents for pets, and pest-attracting perfumes such as cheese flavor, onion flavor, and peanut oil.
本発明化合物は他の殺虫剤、殺ダニ剤、殺菌剤、除草剤、忌避剤、共力剤、肥料、土壌改良材と混用または併用して用いることもできる。 The compound of the present invention can be used in combination with or in combination with other insecticides, acaricides, fungicides, herbicides, repellents, synergists, fertilizers, and soil conditioners.
かかる殺虫剤、殺ダニ剤の有効成分としては、例えば、
(1)合成ピレスロイド系化合物
ピレトリン(pyrethrins)、アレスリン(allethrin)、プラレトリン(prallethrin)、フラメトリン(furamethrin)、レスメトリン(resmethrin)、テトラメトリン(tetramethrin)、イミプロトリン(imiprothrin)、エンペントリン(empenthrin)、トランスフルトリン(transfluthrin)、メトフルトリン(metofluthrin)、プロフルトリン(profluthrin)、フェノトリン(phenothrin)、シフェノトリン(cyphenothrin)、ペルメトリン(permethrin)、シペルメトリン(cypermethrin)、シフルトリン(cyfluthrin)、ベータ−シフルトリン(beta−cyfluthrin)、フェンプロパトリン(fenpropathrin)、ビフェントリン(bifenthrin)、シクロプロトリン(cycloprothrin)、デルタメトリン(deltamethrin)、フルメトリン(flumethrin)、アクリナトリン(acrinathrin)、トラロメトリン(tralomethrin)、シハロトリン(cyhalothrin)、ラムダシハロトリン(lambda−cyhalothrin)、テフルトリン(tefluthrin)、フェンバレレート(fenvalerate)、フルバリネート(fluvalinate)、エトフェンプロックス(ethofenprox)、シラフルオフェン(silafluofen)、モンフルオロスリン(momfluorothrin)、ジメフルトリン(dimefluthrin)、2,3,5,6−テトラフルオロ−4−(メトキシメチル)ベンジル=2,2−ジメチル−3−(2−メチル−1−プロペニル)シクロプロパンカルボキシレート、2,3,5,6−テトラフルオロ−4−(メトキシメチル)ベンジル=2,2,3,3−テトラメチルシクロプロパンカルボキシレート等;
(2)有機リン系化合物
アセフェート(acephate)、ブタチオホス(butathiofos)、ダイアジノン(diazinon)、ジクロルボス(dichlorvos:DDVP)、ジメトエート(dimethoate)、フェンチオン(fenthion:MPP)、フェニトロチオン(fenitrothion:MEP)、マラチオン(malathion)、ピリダフェンチオン(pyridafenthion)、プロパホス(propaphos)、トリクロルホン(trichlorphon:DEP)等;
(3)カーバメート系化合物
カルバリル(carbary1)、カルボフラン(carbofuran)、フェノブカルブ(fenobucarb)、イソプロカルブ(isoprocarb:MIPC)、メソミル(methomyl)、NAC、プロポクスル(propoxur:PHC)等;
(4)ネライストキシン系化合物
カルタップ(cartap)、ベンスルタップ(bensu1tap)等;
(5)ネオニコチノイド系化合物
イミダクロプリド(imidac1oprid)、ニテンピラム(nitenpyram)、アセタミプリド(acetamiprid)、チアメトキサム(thiamethoxam)、チアクロプリド(thiacloprid)、ジノテフラン(dinotefuran)、クロチアニジン(clothianidin)等;
(6)ベンゾイル尿素系化合物
クロルフルアズロン(chlorfluazuron)、ビストリフルロン(bistrifluron)、ジフルベンズロン(diflubenzuron)、フルフェノクスロン(flufenoxuron)、ヘキサフルムロン(hexaflumuron)、テフルベンズロン(teflubenzuron)、トリフルムロン(triflumuron)等;
(7)フェニルピラゾール系化合物
フィプロニル(fiproni1)、ピリプロール(pyriprole)、ピラフルプロール(pyrafluprole)等;
(8)ヒドラジン系化合物
クロマフェノジド(chromafenozide)、ハロフェノジド(halofenozide)、メトキシフェノジド(methoxyfenozide)等;
(9)天然系殺虫剤
マシン油(machine oil)、硫酸ニコチン(nicotine−sulfate);
(10)その他の殺虫剤
アベルメクチン(avermectin−B)、ブプロフェジン(buprofezin)、クロルフェナピル(chlorphenapyr)、ハイドロプレン(hydroprene)、メトプレン(methoprene)、インドキサカルブ(indoxacarb)、メトキサジアゾン(metoxadiazone)、ミルベマイシンA(milbemycin−A)、ピリダリル(pyridalyl)、ピリプロキシフェン(pyriproxyfen)、スピノサッド(spinosad)、スルフラミド(sulfluramid)、トルフェンピラド(tolfenpyrad)、トリアゼメイト(triazamate)、フルベンジアミド(flubendiamide)、シフルメトフェン(cyflumetofen)、臭化メチル(Methyl bromide)、オレイン酸カリウム(Potassium oleate)等が挙げられる。
As an active ingredient of such insecticides and acaricides, for example,
(1) Synthetic pyrethroid compounds pyrethrins, allethrin, praretrin, furamethrin, resmethrin, tetramethrin, imiprothrin, imiprothrin (Transfluthrin), methfluthrin, profluthrin, phenothrin, cyphenothrin, permethrin, cypermethrin, cypermethrin, cypermethrin. uthrin), beta-cyfluthrin, fenpropathrin, bifenthrin, cycloprothrin, deltamethrin (flumethrin), flumethrin (flumethrin) , Cyhalothrin, lambda-cyhalothrin, tefluthrin, fenvalerate, fulvalinate, etofenprox, silaflufen silaflufen), monfluorothrin, dimethylfluthrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2-dimethyl-3- (2-methyl-1-propenyl) ) Cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2,3,3-tetramethylcyclopropanecarboxylate, etc .;
(2) Organophosphorus compounds Acephate, butathiofos, diazinon, dichlorvos (DDVP), dimethoate, fenthion (MPP), fenitrothion (fenepanthion) malathion), pyridafenthion, propaphos, trichlorphone (DEP) and the like;
(3) Carbamate compounds Carbaryl (carbary1), carbofuran, fenobucarb, isoprocarb (MIPC), mesomyl, NAC, propoxur (PHC), etc .;
(4) Nereistoxin compounds, such as cartap and bensultap;
(5) Neonicotinoid compounds imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamipride), thiamethoxam (thiacloprid) (thiacloprid), dinotefur (din)
(6) Benzoylurea compounds Chlorfluazuron, bistrifluron, diflubenzuron, flufenoxuron, hexafluuron, fluflutriuron, fluflutriuron etc;
(7) Phenylpyrazole compound fipronil (pyproni1), pyriprole (pyriprole), pyrafluprole (pyrafluprole) and the like;
(8) Hydrazine-based compounds Chromafenozide, halofenozide, methoxyphenozide and the like;
(9) Natural insecticide machine oil, nicotine sulfate (nicotine-sulfate);
(10) Other insecticides avermectin (vermectin-B), buprofezin, chlorfenapyr, hydroprene, metoprene, toxacarbine, indoxacarb milbemycin-A), pyridalyl, pyriproxyfen, spinosad, sulfuramid, tolfenpyrad, triazemate flude, fludemamide fludefamide Examples thereof include cyflumetofen, methyl bromide, potassium oleate and the like.
忌避剤の有効成分としては、例えばN,N−ジエチル−m−トルアミド、リモネン、リナロール、シトロネラール、メントール、メントン、ヒノキチオール、ゲラニオール、p−メンタン−3,8−ジオール、ユーカリプトール、カラン−3,4−ジオール、IR−3535、MGK−R−326、MGK−R−874、KBR−3023(ピカリジン)等が挙げられる。 As an active ingredient of a repellent, for example, N, N-diethyl-m-toluamide, limonene, linalool, citronellal, menthol, menthone, hinokitiol, geraniol, p-menthane-3,8-diol, eucalyptol, caran-3 , 4-diol, IR-3535, MGK-R-326, MGK-R-874, KBR-3023 (picaridine) and the like.
共力剤の有効成分としては、例えば5−〔2−(2−ブトキシエトキシ)エトキシメチル〕−6−プロピル−1,3−ベンゾジオキソール、N−(2−エチルヘキシル)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、オクタクロロジプロピルエーテル、チオシアノ酢酸イソボルニル、N−(2−エチルへキシル)−1−イソプロピル−4−メチルビシクロ[2.2.2]オクト−5−エン−2,3−ジカルボキシイミド等が挙げられる。 As an active ingredient of a synergist, for example, 5- [2- (2-butoxyethoxy) ethoxymethyl] -6-propyl-1,3-benzodioxole, N- (2-ethylhexyl) bicyclo [2.2 .1] Hept-5-ene-2,3-dicarboximide, octachlorodipropyl ether, isobornyl thiocyanoacetate, N- (2-ethylhexyl) -1-isopropyl-4-methylbicyclo [2.2. 2] Oct-5-ene-2,3-dicarboximide and the like.
本発明化合物が効力を有する有害生物としては、例えば有害昆虫や有害ダニ等の有害節足動物が挙げられ、具体的には以下のものが挙げられる。
双翅目害虫:アカイエカ、コガタアカイエカ等のイエカ類、ネッタイシマカ、ヒトスジシマカ等のヤブカ類、シナハマダラカ等のハマダラカ類、ユスリカ類、イエバエ、オオイエバエ、ヒメイエバエ等のイエバエ類、クロバエ類、ニクバエ類、タネバエ、タマネギバエ等のハナバエ類、ミバエ類、ハモグリバエ類、ショウジョウバエ類、チョウバエ類、ノミバエ類、アブ類、ブユ類、サシバエ類、ヌカカ類等;
網翅目害虫:チャバネゴキブリ、クロゴキブリ、ワモンゴキブリ、トビイロゴキブリ、コバネゴキブリ等;
膜翅目害虫:アリ類、スズメバチ類、アリガタバチ類、カブラハバチ等のハバチ類等;
隠翅目害虫:イヌノミ、ネコノミ、ヒトノミ等;
シラミ目害虫:ヒトジラミ、ケジラミ、アタマジラミ、コロモジラミ等;
等翅目害虫:ヤマトシロアリ、イエシロアリ等;
半翅目害虫:ヒメトビウンカ、トビイロウンカ等のウンカ類、ツマグロヨコバイ等のヨコバイ類、ワタアブラムシ等のアブラムシ類、カメムシ類、トコジラミ等のトコジラミ類等;
鱗翅目害虫:ニカメイガ、コブノメイガ等のメイガ類、ハスモンヨトウ、アワヨトウ、ヨトウガ等のヨトウ類、シンクイガ類、ハモグリガ類、ドクガ類、コナガ、イチモンジセセリ、イガ、コイガ等;
鞘翅目害虫:ヒメカツオブシムシ、ヒメマルカツオブシムシ、コクゾウムシ、アズキゾウムシ等のゾウムシ類、チャイロコメノゴミムシダマシ、コクヌストモドキ等のゴミムシダマシ類、シバンムシ類、ヒラタキクイムシ類等;
ダニ類:コナヒョウヒダニ、ヤケヒョウヒダニ等のヒョウヒダニ類、ケナガコナダニ、ムギコナダニ等のコナダニ類、チリニクダニ、イエニクダニ、サナアシニクダニ等のニクダニ類、クワガタツメダニ、フトツメダニ等のツメダニ類、ホコリダニ類、マルニクダニ類、イエササラダニ類、フタトゲチマダニ等のマダニ類、トリサシダニ、ワクモ等のワクモ類。
Examples of pests for which the compounds of the present invention are effective include harmful arthropods such as harmful insects and harmful mites, and specific examples thereof include the following.
Diptera: Culex mosquitoes, Culex mosquitoes, etc., Aedes aegypti, Aedes albopictus, etc. Mosquitoes, fruit flies, leafhoppers, fruit flies, butterflies, flea flies, fly flies, flyfish, sand flies, nucifers, etc .;
Reticulate pests: German cockroaches, black cockroaches, American cockroaches, flying cockroaches, cockroaches, etc .;
Hymenoptera: ants, wasps, scallops, wasps such as wasps, etc .;
Lepidoptera: Inu fleas, cat fleas, human fleas, etc .;
Lice eye pests: human lice, white lice, head lice, body lice etc .;
Isoptera pests: Yamato termites, termites, etc .;
Hemiptera: insects such as Japanese brown planthoppers, leafhoppers, leafhoppers such as leafhoppers, aphids such as cotton aphids, bed bugs such as stink bugs, bed bugs, etc .;
Lepidopterous pests: Japanese moths, such as Japanese moth, Japanese moth, Japanese moth, Japanese moth, Japanese moth, Siniga, Japanese moth, Japanese moth, Japanese moth, Japanese moth, Japanese moth, Japanese moth, etc .;
Coleopterous insects: weevil such as longhorn beetle, long-horned beetle, weevil, weevil, weevil such as white weevil, bark beetle such as white beetle, hornworm, etc .;
Tick: Leopard mites, such as Scarlet mite, Yake leopard mite, Scarlet mites, such as Scarlet mite, Scarlet mite, Scarlet mites, Scarlet mites, Mite, Mite, Mite Spiders such as ticks, avian mites, and spiders.
本発明の有害生物の防除方法は、本発明化合物の有効量を、通常本発明の有害生物防除剤の形態にて、有害生物又は有害生物の生息場所に施用することにより行われる。
本発明の有害生物防除剤の施用方法としては、例えば以下の方法が挙げられ、本発明の有害生物防除剤の形態、使用場所等に応じて適宜選択できる。
(1)本発明の有害生物防除剤をそのまま有害生物又は有害生物の生息場所に処理する方法。
(2)本発明の有害生物防除剤を水等の溶媒で希釈した後に、有害生物又は有害生物の生息場所に散布処理する方法。
この場合には、通常、乳剤、水和剤、フロアブル剤、マイクロカプセル製剤等に製剤化された本発明の有害生物防除剤を本発明化合物の濃度が0.1〜10000ppmとなるように希釈する。
(3)本発明の有害生物防除剤を有害生物の生息場所で、加熱等の手段により有効成分を揮散させる方法。
この場合、本発明化合物の施用量、施用濃度はいずれも本発明の有害生物防除剤の形態、施用時期、施用場所、施用方法、有害生物の種類、被害状況等に応じて適宜定めることができる。
The pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention to a pest or a pest habitat, usually in the form of the pest control agent of the present invention.
Examples of the application method of the pest control agent of the present invention include the following methods, which can be appropriately selected depending on the form, use place, etc. of the pest control agent of the present invention.
(1) A method of treating the pest control agent of the present invention as it is in a pest or a habitat of the pest.
(2) A method in which the pest control agent of the present invention is diluted with a solvent such as water and then sprayed to a pest or a habitat of the pest.
In this case, the pest control agent of the present invention formulated in an emulsion, wettable powder, flowable agent, microcapsule preparation or the like is usually diluted so that the concentration of the compound of the present invention becomes 0.1 to 10,000 ppm. .
(3) A method of volatilizing an active ingredient by means of heating or the like in a pest habitat where the pest control agent of the present invention is present.
In this case, both the application amount and the application concentration of the compound of the present invention can be appropriately determined according to the form of the pest control agent of the present invention, the application time, the application place, the application method, the type of the pest, the damage situation, etc. .
本発明化合物を害虫防除用として用いる場合は、その施用量は空間に適用するときは、本発明化合物の量として通常0.001〜100mg/m3であり、平面に適用するときは0.001〜100mg/m2である。蚊取線香、蚊取マット等はその製剤形態に応じて加熱により有効成分を揮散させて施用する。樹脂蒸散剤、紙蒸散剤、不織布蒸散剤、編織物蒸散剤、昇華性錠剤等は例えば施用する空間にそのまま放置する、および、該製剤に送風下に設置することにより使用できる。
本発明の有害生物防除組成物を害虫防除用として施用する空間としては、例えば、リビングルーム、食堂、寝室、クローゼット、押入れ、和ダンス、食器棚、トイレ、浴場、物置、倉庫、車内等が挙げられ、さらに野外の開放空間で施用することもできる。
When the compound of the present invention is used for pest control, the application amount is usually 0.001 to 100 mg / m 3 as the amount of the compound of the present invention when applied to a space, and 0.001 when applied to a plane. ˜100 mg / m 2 . Mosquito coils, mosquito coils, etc. are applied by volatilizing the active ingredient by heating according to the formulation form. Resin transpiration agents, paper transpiration agents, non-woven fabric transpiration agents, knitted fabric transpiration agents, sublimable tablets and the like can be used, for example, by leaving them in the space to be applied as they are and by placing them in the preparation under ventilation.
Examples of the space where the pest control composition of the present invention is applied for pest control include, for example, living rooms, cafeterias, bedrooms, closets, closets, Japanese dance, cupboards, toilets, bathhouses, storerooms, warehouses, and the like. In addition, it can be applied in open spaces outside.
本発明の有害生物防除組成物をウシ、ウマ、ブタ、ヒツジ、ヤギ、ニワトリ等の家畜、イヌ、ネコ、ラット、マウス等の小動物の外部寄生虫防除に用いる場合は、獣医学的に公知の方法で動物に使用することができる。具体的な使用方法としては、全身抑制(systemic control)を目的にする場合には、例えば錠剤、飼料混入、坐薬、注射(筋肉内、皮下、静脈内、腹腔内等)により投与され、非全身的抑制(non-systemic control)を目的とする場合には、例えば油剤若しくは水性液剤を噴霧する、ポアオン(pour-on)処理若しくはスポットオン(spot-on)処理する、シャンプー製剤で動物を洗う又は樹脂蒸散剤を首輪や耳札にして動物に付ける等の方法により用いられる。動物体に投与する場合の本発明化合物の量は、通常動物の体重1kgに対して、0.01〜100mgの範囲である。 When the pest control composition of the present invention is used for controlling ectoparasites of domestic animals such as cattle, horses, pigs, sheep, goats and chickens, and small animals such as dogs, cats, rats and mice, it is well known in veterinary medicine. Can be used on animals in any way. As a specific method of use, when systemic control is intended, for example, it is administered by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) For purposes of non-systemic control, for example, spraying oils or aqueous solutions, pour-on treatment or spot-on treatment, washing animals with shampoo formulations or It is used by a method such as attaching a resin transpiration agent to an animal with a collar or ear tag. The amount of the compound of the present invention when administered to an animal body is usually in the range of 0.01 to 100 mg per 1 kg body weight of the animal.
以下、製造例、製剤例及び試験例等により本発明をさらに詳しく説明するが、本発明はこれらの例に限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to production examples, formulation examples, test examples, and the like, but the present invention is not limited to these examples.
まず、本発明化合物の製造例を示す。
製造例1
4−メチル−2,3,5,6−テトラフルオロベンジルアルコール(291mg,1.50mmol)及び(1R,3R)−3−[(E)−2−メトキシカルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸(213mg,1.00mmol)のクロロホルム溶液(5mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(230mg、1.20mmol)及び4−ジメチルアミノピリジン(5mg)を加えた。室温で15時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化6]
Production Example 1
4-Methyl-2,3,5,6-tetrafluorobenzyl alcohol (291 mg, 1.50 mmol) and (1R, 3R) -3-[(E) -2-methoxycarbonyl-1-propenyl] -2,2 -Dichlorocyclopropanecarboxylic acid (213 mg, 1.00 mmol) in chloroform solution (5 mL) to 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (230 mg, 1.20 mmol) and 4-dimethylaminopyridine ( 5 mg) was added. After stirring at room temperature for 15 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chem. 6]
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.22(s,3H)、1.31(s,3H)、1.71(d,1H)、1.93(s,3H)、2.22(dd,1H)、2.28(s,3H)、3.72(s,3H)、5.22(s,2H)、6.43(d、1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.22 (s, 3H), 1.31 (s, 3H), 1.71 (d, 1H), 1.93 (s , 3H), 2.22 (dd, 1H), 2.28 (s, 3H), 3.72 (s, 3H), 5.22 (s, 2H), 6.43 (d, 1H)
製造例2
4−メトキシメチル−2,3,5,6−テトラフルオロベンジルアルコール(100mg,0.44mmol)及び(1R)−3−[(E)−2−メトキシカルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸(78mg,0.37mmol,3R:3S=4:1)のクロロホルム溶液(2mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(86mg、0.37mmol)及び4−ジメチルアミノピリジン(3mg)を加えた。室温で19時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化7]
で示される4−メトキシメチル−2,3,5,6−テトラフルオロベンジル (1R,3R)−3−[(E)−2−メトキシカルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボキシレート(以下、本発明化合物(2)と記す。)79mgを得た。
Production Example 2
4-methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol (100 mg, 0.44 mmol) and (1R) -3-[(E) -2-methoxycarbonyl-1-propenyl] -2,2- 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (86 mg, 0.37 mmol) in a chloroform solution (2 mL) of dimethylcyclopropanecarboxylic acid (78 mg, 0.37 mmol, 3R: 3S = 4: 1) And 4-dimethylaminopyridine (3 mg) was added. After stirring at room temperature for 19 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chem. 7]
4-methoxymethyl-2,3,5,6-tetrafluorobenzyl (1R, 3R) -3-[(E) -2-methoxycarbonyl-1-propenyl] -2,2-dimethylcyclopropanecarboxy 79 mg of a rate (hereinafter referred to as the present compound (2)) was obtained.
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.22(s,3H)、1.31(s,3H)、1.71(d,1H)、1.93(s,3H)、2.22(dd,1H)、3.40(s,3H)、3.72(s,3H)、4.59(s,2H)、5.24(s,2H)、6.44(d、1H)
さらに極性の高い成分として、下記式[化8]
As a more polar component, the following formula [Chemical Formula 8]
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.26(s,3H)、1.31(s,3H)、1.90(m,1H)、1.91(s,3H)、1.99(m,1H)、3.40(s,3H)、3.74(s,3H)、4.58(s,2H)、5.21(m,2H)、7.02(d、1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.26 (s, 3H), 1.31 (s, 3H), 1.90 (m, 1H), 1.91 (s , 3H), 1.99 (m, 1H), 3.40 (s, 3H), 3.74 (s, 3H), 4.58 (s, 2H), 5.21 (m, 2H), 7 .02 (d, 1H)
製造例3
2,3,5,6−テトラフルオロベンジルアルコール(57mg,0.32mmol)及び(1R)−3−[(E)−2−メトキシカルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸(56mg,0.26mmol,3R:3S=4:1)のクロロホルム溶液(2mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(61mg、0.32mmol)及び4−ジメチルアミノピリジン(3mg)を加えた。室温で17時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化9]
2,3,5,6-tetrafluorobenzyl alcohol (57 mg, 0.32 mmol) and (1R) -3-[(E) -2-methoxycarbonyl-1-propenyl] -2,2-dimethylcyclopropanecarboxylic acid 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (61 mg, 0.32 mmol) and 4-dimethylamino were added to a chloroform solution (2 mL) of (56 mg, 0.26 mmol, 3R: 3S = 4: 1). Pyridine (3 mg) was added. After stirring at room temperature for 17 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chemical Formula 9]
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.22(s,3H)、1.31(s,3H)、1.72(d,1H)、1.93(s,3H)、2.21(dd,1H)、3.72(s,3H)、5.25(s,2H)、6.44(d、1H)、7.10(s,1H)
さらに極性の高い成分として、下記式[化10]
Furthermore, as a highly polar component, the following formula [Chemical Formula 10]
無色液体:1H−NMR(CDCl3,TMS)δ(ppm): 1.26(s,3H)、1.32(s,3H)、1.88(m,1H)、1.90(s,3H)、1.99(m,1H)、3.74(s,3H)、5.27(m,2H)、7.02(d、1H)、7.20(m,1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.26 (s, 3H), 1.32 (s, 3H), 1.88 (m, 1H), 1.90 (s) , 3H), 1.99 (m, 1H), 3.74 (s, 3H), 5.27 (m, 2H), 7.02 (d, 1H), 7.20 (m, 1H)
製造例4
4−エチニル−2,3,5,6−テトラフルオロベンジルアルコール(96mg,0.47mmol)及び(1R,3R)−3−[(E)−2−メトキシカルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸(66mg,0.31mmol)のクロロホルム溶液(2mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(72mg、0.38mmol)及び4−ジメチルアミノピリジン(3mg)を加えた。室温で17時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化11]
で示される4−エチニル−2,3,5,6−テトラフルオロベンジル (1R,3R)−3−[(E)−2−メトキシカルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボキシレート(以下、本発明化合物(6)と記す。)71mgを得た。
Production Example 4
4-ethynyl-2,3,5,6-tetrafluorobenzyl alcohol (96 mg, 0.47 mmol) and (1R, 3R) -3-[(E) -2-methoxycarbonyl-1-propenyl] -2,2 -Dichlorocyclopropanecarboxylic acid (66 mg, 0.31 mmol) in chloroform (2 mL) was added to 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (72 mg, 0.38 mmol) and 4-dimethylaminopyridine ( 3 mg) was added. After stirring at room temperature for 17 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chem. 11]
4-ethynyl-2,3,5,6-tetrafluorobenzyl (1R, 3R) -3-[(E) -2-methoxycarbonyl-1-propenyl] -2,2-dimethylcyclopropanecarboxylate (Hereinafter referred to as the present compound (6).) 71 mg was obtained.
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.22(s,3H)、1.31(s,3H)、1.71(d,1H)、1.93(s,3H)、2.22(dd,1H)、3.67(s,1H)、3.72(s,3H)、5.22(s,2H)、6.43(d、1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.22 (s, 3H), 1.31 (s, 3H), 1.71 (d, 1H), 1.93 (s , 3H), 2.22 (dd, 1H), 3.67 (s, 1H), 3.72 (s, 3H), 5.22 (s, 2H), 6.43 (d, 1H)
製造例5
4−メチル−2,3,5,6−テトラフルオロベンジルアルコール(76mg,0.39mmol)及び(1R,3R)−3−[(E)−2−エトキシカルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸(74mg,0.39mmol)のクロロホルム溶液(3mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(69mg、0.36mmol)及び4−ジメチルアミノピリジン(3mg)を加えた。室温で22時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化12]
で示される4−メチル−2,3,5,6−テトラフルオロベンジル (1R,3R)−3−[(E)−2−エトキシカルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボキシレート(以下、本発明化合物(7)と記す。)58mgを得た。
Production Example 5
4-Methyl-2,3,5,6-tetrafluorobenzyl alcohol (76 mg, 0.39 mmol) and (1R, 3R) -3-[(E) -2-ethoxycarbonyl-1-propenyl] -2,2 -Dimethylcyclopropanecarboxylic acid (74 mg, 0.39 mmol) in chloroform (3 mL) to 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (69 mg, 0.36 mmol) and 4-dimethylaminopyridine ( 3 mg) was added. After stirring at room temperature for 22 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chem. 12]
4-methyl-2,3,5,6-tetrafluorobenzyl (1R, 3R) -3-[(E) -2-ethoxycarbonyl-1-propenyl] -2,2-dimethylcyclopropanecarboxylate (Hereinafter referred to as the present compound (7).) 58 mg was obtained.
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.22(s,3H)、1.28(t,3H)、1.31(s,3H)、1.71(d,1H)、1.93(s,3H)、2.21(dd,1H)、2.29(s,3H)、4.18(q,2H)、5.22(s,2H)、6.43(d、1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.22 (s, 3H), 1.28 (t, 3H), 1.31 (s, 3H), 1.71 (d , 1H), 1.93 (s, 3H), 2.21 (dd, 1H), 2.29 (s, 3H), 4.18 (q, 2H), 5.22 (s, 2H), 6 .43 (d, 1H)
製造例6
4−メチル−2,3,5,6−テトラフルオロベンジルアルコール(46mg,0.24mmol)及び(1R,3R)−3−[(E)−2−(1−プロピルオキシ)カルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸(47mg,0.20mmol)のクロロホルム溶液(2mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(45mg、0.24mmol)及び4−ジメチルアミノピリジン(3mg)を加えた。室温で24時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化13]
で示される4−メチル−2,3,5,6−テトラフルオロベンジル (1R,3R)−3−[(E)−2−(1−プロピルオキシ)カルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボキシレート(以下、本発明化合物(8)と記す。)42mgを得た。
Production Example 6
4-Methyl-2,3,5,6-tetrafluorobenzyl alcohol (46 mg, 0.24 mmol) and (1R, 3R) -3-[(E) -2- (1-propyloxy) carbonyl-1-propenyl ] -2,2-dimethylcyclopropanecarboxylic acid (47 mg, 0.20 mmol) in chloroform (2 mL) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (45 mg, 0.24 mmol) and 4 -Dimethylaminopyridine (3 mg) was added. After stirring at room temperature for 24 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chem. 13]
4-methyl-2,3,5,6-tetrafluorobenzyl (1R, 3R) -3-[(E) -2- (1-propyloxy) carbonyl-1-propenyl] -2,2- 42 mg of dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound (8)) was obtained.
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):0.95(t,3H)、1.21(s,3H)、1.31(s,3H)、1.67(m,2H)、1.71(d,1H)、1.93(s,3H)、2.21(dd,1H)、2.28(s,3H)、4.08(t,2H)、5.22(s,2H)、6.43(d、1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 0.95 (t, 3H), 1.21 (s, 3H), 1.31 (s, 3H), 1.67 (m , 2H), 1.71 (d, 1H), 1.93 (s, 3H), 2.21 (dd, 1H), 2.28 (s, 3H), 4.08 (t, 2H), 5 .22 (s, 2H), 6.43 (d, 1H)
製造例7
4−メチル−2,3,5,6−テトラフルオロベンジルアルコール(40mg,0.21mmol)及び(1R,3R)−3−[(E)−2−(2−プロピルオキシ)カルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸(33mg,0.14mmol)のクロロホルム溶液(3mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(32mg、0.17mmol)及び4−ジメチルアミノピリジン(3mg)を加えた。室温で24時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化14]
で示される4−メチル−2,3,5,6−テトラフルオロベンジル (1R,3R)−3−[(E)−2−(2−プロピルオキシ)カルボニル−1−プロペニル]−2,2−ジメチルシクロプロパンカルボキシレート(以下、本発明化合物(9)と記す。)31mgを得た。
Production Example 7
4-Methyl-2,3,5,6-tetrafluorobenzyl alcohol (40 mg, 0.21 mmol) and (1R, 3R) -3-[(E) -2- (2-propyloxy) carbonyl-1-propenyl ] -2,2-dimethylcyclopropanecarboxylic acid (33 mg, 0.14 mmol) in chloroform solution (3 mL) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (32 mg, 0.17 mmol) and 4 -Dimethylaminopyridine (3 mg) was added. After stirring at room temperature for 24 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chem. 14]
4-methyl-2,3,5,6-tetrafluorobenzyl (1R, 3R) -3-[(E) -2- (2-propyloxy) carbonyl-1-propenyl] -2,2- 31 mg of dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound (9)) was obtained.
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.21(s,3H)、1.24(d,6H)、1.31(s,3H)、1.71(d,1H)、1.91(s,3H)、2.21(dd,1H)、2.29(s,3H)、5.03(m,1H)、5.22(m,2H)、6.40(d、1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.21 (s, 3H), 1.24 (d, 6H), 1.31 (s, 3H), 1.71 (d , 1H), 1.91 (s, 3H), 2.21 (dd, 1H), 2.29 (s, 3H), 5.03 (m, 1H), 5.22 (m, 2H), 6 .40 (d, 1H)
製造例8
4−エチニル−2,3,5,6−テトラフルオロベンジルアルコール(100mg,0.50mmol)及び(1R,3S)−3−[(Z)−3−メトキシ−3−オキソ−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸(100mg,0.49mmol)のクロロホルム溶液(4mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(141mg、0.74mmol)及び4−ジメチルアミノピリジン(5mg)を加えた。室温で24時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化15]
4-ethynyl-2,3,5,6-tetrafluorobenzyl alcohol (100 mg, 0.50 mmol) and (1R, 3S) -3-[(Z) -3-methoxy-3-oxo-1-propenyl]- To a chloroform solution (4 mL) of 2,2-dimethylcyclopropanecarboxylic acid (100 mg, 0.49 mmol) was added 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (141 mg, 0.74 mmol) and 4-dimethyl. Aminopyridine (5 mg) was added. After stirring at room temperature for 24 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chemical Formula 15]
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.28(s,3H)、1.30(s,3H)、1.94(d,1H)、3.27(t,1H)、3.67(s,1H)、3.72(s,3H)、5.20(s,2H)、5.92(d、1H)、6.60(t、1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.28 (s, 3H), 1.30 (s, 3H), 1.94 (d, 1H), 3.27 (t , 1H), 3.67 (s, 1H), 3.72 (s, 3H), 5.20 (s, 2H), 5.92 (d, 1H), 6.60 (t, 1H)
製造例9
4−メチル−2,3,5,6−テトラフルオロベンジルアルコール(42mg,0.21mmol)及び(1R,3R)−3−オキソ−[(E)−2,2,2−トリフルオロエトキシ−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸(50mg,0.18mmol)のクロロホルム溶液(2mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(41mg、0.21mmol)及び4−ジメチルアミノピリジン(3mg)を加えた。室温で24時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化16]
4-Methyl-2,3,5,6-tetrafluorobenzyl alcohol (42 mg, 0.21 mmol) and (1R, 3R) -3-oxo-[(E) -2,2,2-trifluoroethoxy-1 -Propenyl] -2,2-dimethylcyclopropanecarboxylic acid (50 mg, 0.18 mmol) in chloroform solution (2 mL) 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (41 mg, 0.21 mmol) And 4-dimethylaminopyridine (3 mg) was added. After stirring at room temperature for 24 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chem. 16]
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.23(s,3H)、1.32(s,3H)、1.77(d,1H)、1.96(s,3H)、2.24(m,1H)、2.29(s,3H)、4.50(m,3H)、5.22(d,2H)、6.53(d、1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.23 (s, 3H), 1.32 (s, 3H), 1.77 (d, 1H), 1.96 (s , 3H), 2.24 (m, 1H), 2.29 (s, 3H), 4.50 (m, 3H), 5.22 (d, 2H), 6.53 (d, 1H)
製造例10
4−メチル−2,3,5,6−テトラフルオロベンジルアルコール(50mg,0.26mmol)及び(1R,3R)−3−オキソ−[(E)−2,2,2−トリフルオロ−1−(トリフルオロ)エトキシ−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸(67mg,0.19mmol)のクロロホルム溶液(2mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(50mg、0.26mmol)及び4−ジメチルアミノピリジン(3mg)を加えた。室温で24時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化17]
4-Methyl-2,3,5,6-tetrafluorobenzyl alcohol (50 mg, 0.26 mmol) and (1R, 3R) -3-oxo-[(E) -2,2,2-trifluoro-1- 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride in a chloroform solution (2 mL) of (trifluoro) ethoxy-1-propenyl] -2,2-dimethylcyclopropanecarboxylic acid (67 mg, 0.19 mmol) (50 mg, 0.26 mmol) and 4-dimethylaminopyridine (3 mg) were added. After stirring at room temperature for 24 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chemical Formula 17]
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.24(s,3H)、1.33(s,3H)、1.83(d,1H)、2.00(s,3H)、2.27(m,1H)、2.29(s,3H)、4.50(m,3H)、5.23(m,2H)、5.82(m、1H)、6.63(m、1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.24 (s, 3H), 1.33 (s, 3H), 1.83 (d, 1H), 2.00 (s , 3H), 2.27 (m, 1H), 2.29 (s, 3H), 4.50 (m, 3H), 5.23 (m, 2H), 5.82 (m, 1H), 6 .63 (m, 1H)
次に、製剤例を示す。なお、部は質量部を示す。 Next, formulation examples are shown. In addition, a part shows a mass part.
製剤例1
本発明化合物(1)〜(12)の各々0.1部をキシレン 10部に溶解し、これを脱臭灯油 89.9部に混合して、油剤を得る。
Formulation Example 1
0.1 parts of each of the compounds (1) to (12) of the present invention are dissolved in 10 parts of xylene and mixed with 89.9 parts of deodorized kerosene to obtain an oil agent.
製剤例2
本発明化合物(1)〜(12)の各々0.3gにケロシンを加えて100mLとした溶液をエアゾール容器に充填し、バルブを取り付けた後、該バルブ部分を通じて噴射剤(液化石油ガス、ジメチルエーテルの混合ガス)200mLを加圧充填してエアゾールを得た。
Formulation Example 2
A solution obtained by adding kerosene to 0.3 g of each of the compounds (1) to (12) of the present invention to make 100 mL is filled in an aerosol container, and after a valve is attached, a propellant (liquefied petroleum gas, dimethyl ether 200 mL of mixed gas) was pressurized and filled to obtain an aerosol.
製剤例3
本発明化合物(1)〜(12)の各々0.6部、キシレン 5部、脱臭灯油 3.4部及びレオドールMO−60 (乳化剤、花王株式会社登録商標) 1部を混合溶解したものと、水 50部とをエアゾール容器に充填し、バルブ部分を通じて噴射剤(液化石油ガス) 40部を加圧充填して、水性エアゾールを得る。
Formulation Example 3
0.6 parts of each of the compounds (1) to (12) of the present invention, 5 parts of xylene, 3.4 parts of deodorized kerosene and 1 part of Rhedol MO-60 (emulsifier, registered trademark of Kao Corporation) An aerosol container is filled with 50 parts of water, and 40 parts of propellant (liquefied petroleum gas) is pressurized and filled through a valve portion to obtain an aqueous aerosol.
製剤例4
本発明化合物(1)〜(12)の各々0.3g及びBHT0.5gを、蚊取線香用基材(除虫菊抽出粕粉、木粉、タブ粉、及び澱粉を混合したもの) 99.2gに均一に攪拌混合した後、着色剤としてマラカイトグリーンを含む水 100mLを加え、十分混練したものを成型乾燥し、蚊取線香を得る。
Formulation Example 4
The compound (1) to (12) of the present invention (0.3 g) and BHT (0.5 g) were each added to 99.2 g of a base material for mosquito coils (mixed with insecticide chrysanthemum extract powder, wood powder, tab powder, and starch). After stirring and mixing uniformly, 100 mL of water containing malachite green is added as a colorant, and the mixture is kneaded and dried to obtain a mosquito coil.
製剤例5
本発明化合物(1)〜(12)の各々0.8g、ピペロニルブトキシド 0.4g、及び染料に脱臭灯油を加えて溶解し、全部で10mLとする。この溶液 0.5mLを22mm×35mm、厚さ2.8mmの蚊取マット用基材(コットンリンターとパルプの混合物のフィリブルを板状に固めたもの)に均一に含浸させて、蚊取マット剤を得る。
Formulation Example 5
Deodorized kerosene is added to and dissolved in 0.8 g of each of the compounds (1) to (12) of the present invention, 0.4 g of piperonyl butoxide, and the dye to make a total of 10 mL. 0.5 ml of this solution is impregnated uniformly into a substrate for mosquito mats with a thickness of 22 mm x 35 mm and a thickness of 2.8 mm (a mixture of cotton linter and pulp mixed in a plate shape) Get.
製剤例6
本発明化合物(1)〜(12)の各々0.7部及びBHT0.3部を、界面活性剤(ジエチレングリコールモノブチルエーテル)50部と精製水49部に溶解して得られる液剤をポリエステル製容器に入れ、上部をヒーターで加熱できるようにした吸液芯(無機粉体を焼成したもの)を挿入することにより、加熱蒸散装置に用いる水性蚊取リキッド剤を得る。
Formulation Example 6
A solution obtained by dissolving 0.7 parts of each of the compounds (1) to (12) of the present invention and 0.3 part of BHT in 50 parts of a surfactant (diethylene glycol monobutyl ether) and 49 parts of purified water is placed in a polyester container. An aqueous mosquito repellent liquid agent used in a heat transpiration device is obtained by inserting a liquid absorption core (in which inorganic powder is baked) whose upper part can be heated with a heater.
製剤例7
本発明化合物(1)〜(12)の各々3.0部、メトキサジアゾン3.0部及びアゾジカルボンアミド94.0部をよく混合後、その20gをプラスチックフィルム袋に充填し、これを耐熱容器に収納するとともに点火具を装填して燻煙剤を得た。
Formulation Example 7
After thoroughly mixing 3.0 parts of each of the compounds (1) to (12) of the present invention, 3.0 parts of methoxadiazone and 94.0 parts of azodicarbonamide, 20 g of the mixture is filled into a plastic film bag, and this is put into a heat-resistant container. A smoke agent was obtained by storing and igniter loaded.
製剤例8
本発明化合物(1)〜(12)の各々10mgを適量のアセトンに溶解し、5cm×5cm、厚さ0.3mmの不織布に均一に塗布した後、アセトンを風乾して、常温揮散剤を得る。
Formulation Example 8
10 mg of each of the compounds (1) to (12) of the present invention is dissolved in an appropriate amount of acetone and uniformly applied to a nonwoven fabric having a size of 5 cm × 5 cm and a thickness of 0.3 mm, and then acetone is air-dried to obtain a room temperature volatilizer. .
製剤例9
本発明化合物(1)〜(12)の各々10部、ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩50部を含むホワイトカーボン35部、及び水55部を混合し、湿式粉砕法で微粉砕することにより、10%フロアブル剤を得る。
Formulation Example 9
By mixing 10 parts of each of the compounds (1) to (12) of the present invention, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water, and finely pulverizing with a wet pulverization method, 10% flowable is obtained.
次に、本発明化合物が有害生物防除剤の有効成分として有効であることを試験例として示す。 Next, it shows as a test example that this invention compound is effective as an active ingredient of a pest control agent.
効果試験例1(アカイエカを用いたノックダウン試験)
直径28mm、内高13mm、底面積6.15cm2であるシャーレに本発明化合物である(1),(2),(4),(5),(6),(7),(10)を0.001mg含む 0.002%アセトン溶液0.05mLを滴下し、底面に均一になるよう拡げた後、風乾でアセトンを除去する。各試料が底面に保持されたシャーレに、アカイエカの雌3匹を入れ、穴あきフィルムで上側をカバーした後、5分毎にノックダウン数を記録し、KT50(50%ノックダウンする時間)と24時間後の致死率を測定しかつ記録した。
また、比較対照として下記式[化18]
で示される5−メトキシメチル−2,3,5,6−テトラフルオロベンジル (1R)−トランス−3−(2−シアノ−1−プロペニル)−2,2−ジメチルシクロプロパンカルボキシレート(特許第4285045号公報に記載の化合物。以下、比較化合物(1)と記す。)およびフタルスリン:1,3,4,5,6,7−ヘキサヒドロ−1,3−ジオキソ−2H−イソインド−2−イル (1RS)−トランス、シス−3−(2−メチル−1−プロペニル)−2,2−ジメチルシクロプロパンカルボキシレート(以下、比較化合物(2)と記す。)を用い、同様に試験を行った。
結果を表1に示す。
Effect Test Example 1 (Knockdown test using Culex squid)
(1), (2), (4), (5), (6), (7), (10), which is the compound of the present invention, is applied to a petri dish having a diameter of 28 mm, an inner height of 13 mm, and a bottom area of 6.15 cm 2. After adding 0.001 mg of 0.002% acetone solution 0.05 mL dropwise and spreading evenly on the bottom, acetone is removed by air drying. Place 3 female squids in a petri dish with each sample held on the bottom, cover the top with a perforated film, and record the number of knockdowns every 5 minutes. KT 50 (Time to knock down 50%) The mortality after 24 hours was measured and recorded.
Further, as a comparative control, the following formula [Chemical Formula 18]
5-methoxymethyl-2,3,5,6-tetrafluorobenzyl (1R) -trans-3- (2-cyano-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (Patent No. 4285045) (Hereinafter referred to as comparative compound (1)) and phthalthrin: 1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindo-2-yl (1RS) ) -Trans, cis-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as comparative compound (2)) was similarly tested.
The results are shown in Table 1.
試験の結果、本発明化合物である(1),(2),(4),(5),(6),(7)及び(10)は、いずれも比較化合物(2)(フタルスリン)と同等以上の高いノックダウン活性を示した。なかでも、本発明化合物(1)及び(10)は比較化合物(1)と比較しても同等以上の高いノックダウン活性を示した。さらに、本発明化合物(1),(4),(5),(6),(7)及び(10)は比較化合物(1)及び(2) (フタルスリン)を上回る致死活性を示した。 As a result of the test, the compounds of the present invention (1), (2), (4), (5), (6), (7) and (10) are all equivalent to the comparative compound (2) (phthalthrin). The above high knockdown activity was shown. Among them, the compounds (1) and (10) of the present invention showed a knockdown activity equal to or higher than that of the comparative compound (1). Further, the compounds (1), (4), (5), (6), (7) and (10) of the present invention showed a lethal activity exceeding the comparative compounds (1) and (2) (phthalthrin).
効果試験例2(アカイエカを用いたノックダウン試験)
直径28mm、内高13mm、底面積6.15cm2であるシャーレに本発明化合物である(1),(8)及び(11)を0.0001mg含む 0.002%アセトン溶液0.05mLを滴下し、底面に均一になるよう拡げた後、風乾でアセトンを除去する。各試料が底面に保持されたシャーレに、アカイエカの雌3匹を入れ、穴あきフィルムで上側をカバーした後、5分毎にノックダウン数を記録し、KT50(50%ノックダウンする時間)と24時間後の致死率を測定しかつ記録した。
また、比較対照として前記比較化合物(1)及び比較化合物(2)を用い、同様に試験を行った。
結果を表2に示す。
Effect test example 2 (knock-down test using squid)
To a petri dish having a diameter of 28 mm, an inner height of 13 mm, and a bottom area of 6.15 cm 2 , 0.05 mL of a 0.002% acetone solution containing 0.0001 mg of the compounds of the present invention (1), (8) and (11) was added dropwise. After spreading evenly on the bottom, acetone is removed by air drying. Place 3 female squids in a petri dish with each sample held on the bottom, cover the top with a perforated film, and record the number of knockdowns every 5 minutes. KT 50 (Time to knock down 50%) The mortality after 24 hours was measured and recorded.
Moreover, it tested similarly using the said comparison compound (1) and the comparison compound (2) as a comparison control.
The results are shown in Table 2.
試験の結果、本発明化合物である(1),(5)及び(10)は、いずれも比較化合物(1)及び(2)(フタルスリン)と比較しても同等以上の高いノックダウン活性を示した。また、本発明化合物(1),(5)及び(10)は、いずれも比較化合物(1)及び(2) (フタルスリン)を上回る致死活性を示した。 As a result of the test, the compounds of the present invention (1), (5) and (10) all showed high knockdown activity equal to or higher than that of the comparative compounds (1) and (2) (phthalthrin). It was. In addition, the compounds (1), (5) and (10) of the present invention all exhibited lethal activity exceeding that of the comparative compounds (1) and (2) (phthalthrin).
効果試験例3(蚊取線香による殺虫試験)
70cm立方のガラスチャンバー内にアカイエカ成虫約50匹を放ち、電池式小型扇風機(羽根の径13cm)を箱内に設置し回転させた。そこへ製剤例4によって得られた本発明化合物(2)、(3)、(4)、(10)の蚊取線香0.1gの両端に点火したものを入れると、15分以内に80%以上のアカイエカをノックダウンさせることができ、翌日にはその80%以上を致死させることができた。
Effect test example 3 (insecticidal test with mosquito coils)
About 50 adult mosquitoes were released in a 70 cm cubic glass chamber, and a battery-type small fan (feather diameter 13 cm) was placed in a box and rotated. When ignited at both ends of 0.1 g of the mosquito coils of the present invention (2), (3), (4) and (10) obtained in Formulation Example 4 was added 80% within 15 minutes. The above squid were knocked down, and 80% or more of them were killed the next day.
効果試験例4(燻煙剤による殺虫試験)
製剤例7に準じて調製した本化合物(1)、(6)、(7)の燻煙剤1袋を6畳の部屋でヒーターを用いて約250℃に加熱したところ、プラスチックフィルムで形成された噴煙孔から成分が部屋全体に拡散し、ゴキブリ、ノミ、トコジラミをはじめ、ヒョウヒダニやケナガコナダニ等の屋内塵性ダニ類の防除にも効果的であった。
Effect test example 4 (insecticidal test with smoke smoke agent)
When one bag of smoke compound of the present compound (1), (6), (7) prepared according to Formulation Example 7 was heated to about 250 ° C. with a heater in a 6 tatami room, it was formed with a plastic film. The components diffused from the fumaroles and were effective in controlling indoor dust mites such as cockroaches, fleas, bed bugs, leopard mites, and white mites.
効果試験例5(エアゾールによる殺虫試験)
60cm立方のガラスチャンバー内にイエバエ雌成虫約30匹を放ち、チャンバーの側壁の孔から、製剤例2によって得られた本発明化合物(1)、(2)、(4)、(6)、(10)のエアゾールを1秒間噴霧した。その結果、2分以内に100%のイエバエをノックダウンさせることができた、本発明化合物は高いノックダウン効果を有していることが認められた。
Effectiveness test example 5 (insecticidal test with aerosol)
About 30 housefly adults were released in a 60 cm cubic glass chamber, and the compound of the present invention (1), (2), (4), (6), (6) obtained from Formulation Example 2 from the hole in the side wall of the chamber. The aerosol of 10) was sprayed for 1 second. As a result, it was confirmed that the compound of the present invention, which could knock down 100% of the house fly within 2 minutes, had a high knockdown effect.
本発明化合物は優れた有害生物防除効力を有することから、有害生物防除剤の有効成分として有用である。 Since the compound of the present invention has an excellent pest control effect, it is useful as an active ingredient of a pest control agent.
Claims (7)
A method for controlling pests, wherein the effective amount of the ester compound according to any one of claims 1 to 5 is applied to pests or habitats of pests , except for use on the human body .
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