AU627793B2 - Method for controlling insects and/or acarines - Google Patents

Description

I 1 41

AUSTRALIA

PATENTS ACT 1952 COMPLETE SPECIFICATION 627793 Form

(ORIGINAL)

FOR OFFICE USE Short Title: Int. Cl: Application Number: Lodged: Complete Specification-Lodged: Accepted: Lapsed: S* a Published: Priority: Related Art: TO BE COMPLETED BY APPLICANT Name of Applicant: Address of Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED 5-33, KITAHAMA-4-CHOME

CHUO-KU

OSAKA

JAPAN

Actual Inventor: o Address for Service: GRIFFITH HACK CO., 601 St. Kilda Road, Melbourne, Victoria 3004, Australia.

Complete Specification for the invention entitled: METHOD FOR CONTROLLING INSECTS AND/OR ACARINES.

The following statement is a full description of this invention including the best method of performing it known to me:-

I!

I

1 The present invention relates to a method for controlling insects and/or acarines which comprises vaporizing an active ingredient by mildly heating the same.

0 oo 0 00 0 00 oo0 00 0 0 Q 0 4 0 00000 0 0 a 0o 0 0 0 00 Although various methods for controlling insects and/or acarines are known today, such a method comprising vaporizing a pyrethroid compound by mildly heating the same is scarecely ever known. An isolated instance for such a method is the method with 1-ethynyl- 10 2-methyl-2-pentenyl chrysanthemate disclosed in JP-A-56- 75411.

However, unless used in a considerably large amount, l-ethynyl-2-methyl-2-pentenyl chrysanthemate is not necessarily effective in controlling pests especial- 15 ly in a wide space such as room, storage chamber, closet, warehouse, vehicle, ship, airplane, store, cattle shed, stable, drainage trench, sewer, etc. Also for duration of the effect for a long period of time, this agent should be used in a large amount.

Vaporization of an active ingredient by intensely heating is sometimes effective in enhancing the initial efficacy. But, saving in energy is required for protecting the earth environment. If an active ingredient can be vaporized using surplus or unutilized heat generated by a heating appliance, a lighting 1Ar -2appliance, etc., it will become possible to save precious energy.

There is a method comprising burning a carrier for vaporizing an active agent as in, for example, mosquito coil. Needless to say, according to a method comprising vaporizing an active ingredient by the use of surplus or unutilized heat generated by a heating appliance, a lighting appliance, etc., it is also possible to prevent fuming, burn and fire which might occur by the method comprising burning a carrier.

According to the present invention, there is provided a method for controlling insects and/or acarines comprising vaporizing certain isomers of l-ethynyl-2methyl-2-pentenyl 3-(2,2-dichloroethenyl)-2,2dimethylcyclo-propanecarboxylate (hereinafter Compound I) having the formula,

C

2

H

5

/CH

3

O

C=C CH=CC12 H CH-O-C-CH-CH

[II

C C

C

H H 3 C CH3 0 oV by mildly heating the same.

The said isomers are: I(A) (lS) -l-ethynyl-2-methyl-2-pentenyl (lR)- 20 trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate I(B) (1S)-l-ethynyl-2-methyl-2-pentenyl (1RS)trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate I(C) (1RS)-l-ethynyl-2-methyl-2-pentenyl (lR)trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate -3- The present inventors earnestly investigated a method for effectively controlling insects and/or acarines comprising vaporizing an active ingredient by mild heating, and consequently found that out of numerous well-known insecticidal and acaricidal agents, the abovementioned isomers of Compound I are exceptionally suitable for the object of the present invention, whereby the present invention was accomplished.

It has been disclosed in JP-B-55-42045 that Compound I has an insecticidal and acaricidal activity.

The present inventors, however, found that mere vaporization of the abovementioned isomers of said compound by mild heating has a high initial activity against insects and/or acarines and that the activity lasts for a long period of time, whereby the present inventors were led to the present invention.

n The term "mild heating" used herein means heating 1 4 at a temperature not higher than about 100 0 C but higher than 50 0 C. Such heating can easily be obtained using o 20 surplus or unutilized heat generated by a chemical heat u generator such as pocket heater, or a heating element such as electric heater.

The method of the present invention is effective against various insect pests and acarine pests. It is markedly effective against hygienic pests, wood pests, food S° stuff pests, household nuisance pests, etc. Particularly, i t is most effective against hygienic pests and household 0 nuisance pests.

Specific examples of insect pests and acarine 0 30 pests to which the method of the present invention can be applied are given below.

o 0

TO

-e 1 Lepidoptera Plodia interpunctella (Indian meal moth), etc.

Diptera Culex spp. (common mosquitoes), Anopheles spp.

(Anopheline mosquitoes), Aedes spp., Muscidae (house flies), Drosophilidae (wine flies), Psychodidae (moth flies), Chironomidae (chironomid midges), Calliphoridae (blow flies), Sarcophagidae (fresh flies), Simuliidae (black flies), Tabaridae (tabanid flies), Stomoxyidae (stable flies), etc.

0 0 Coleoptera Q 0O Sitophilus zeamais (maize weevil), Callosobruchus chinensis (adzuki bean weevil), Tribolium castaneum (red fluor beetle), Anobiidae (deathwatch and S 15 drugstore beetles), Lyctidae (powder post beetles), Paederus fuscipes (robe beetle) etc.

Dictyoptera 004* Blattella germanica (German cockroach), ao .Periplaneta fuliginosa (smokybrown cockroach), S 20 Periplaneta americana (American cockroach), Periplaneta brunnea (brown cockroach), Blatta orientalis (oriental cockroach), etc.

o Hymenoptera Formicidae (ants), Bethylidae (bethylid wasps), etc.

Siphonaptera Pulex irritans, etc.

4 4, 5 Anoplura Pediculus humanus capitis (body louse), Pthirus pubis (crab louse), etc.

Isoptera Reticulitermes speratus, Coptotermes formosanus (Formosan subterranean termite), etc.

Acarina Mites associated with house dust and stored food, such as Acaridae, Pyroglyphidae, Cheyletidae, and the like, Ixodidae such as Boophilus microplus, and the like, Dermanyssidae, etc.

For controlling insects and/or acarines by vaporizing the compounds of the invention a carrier is not always necessary. Usually, however, the said compounds are used after being supported on a suitable carrier.

Specific examples of carrier for adsorption used 0o0 for this purpose are papers such as filter paper, cardboard o and the like; pulp; resins such as polyethylene, polypropylene, vinyl chloride and the like; ceramics; 20 asbestos; glass fiber; carbon fiber; chemical fibers; natural fibers; nonwoven fabrics; porous polymer films; porous glass materials; porous absorbent wicks; substrates for electric fumigating mat (a plate formed of fibril of a mixture of cotton linter and pulp); diatomaceous earth; etc. These carriers which have the said compounds 0 0 supported thereon can be used in any preparation form.

The vaporizing efficiency can be further increased by adding subliming materials such as adamantane, ocyclododecane, trimethylnorbornane, etc., as adjuvant for promoting the vaporization.

It is also possible to enhance the efficacy by using the compounds in admixture with known synergists effective for allethrin and pyrethrins, etc., specific examples of which being synergists for pyrethroid such as a-[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2propyltoluene (piperonyl butoxide), N-(2-ethylhexyl)- bicyclo[2,22,1]hepta-5-ene-2,3-dicarboxyimide (MGK-2640), i octachlorodiisopropyl ether Synepirin-500 etc.

w 7 tit T 0ro^V 6 The efficacy of the compounds of the invention can be stabilized by using the said compounds as a blend with an antioxidant and an ultraviolet absorber for increasing the stability to light, heat, oxidation, etc.

Specific examples of the antioxidant are 2,2'methylenebis(6-tert-butyl-4-ethylphenol), 2,6-di-tertbutyl-4-methylphenol (BHT), 2,6-di-tert-butylphenol, 2,2'methylenebis(6-tert-butyl-4-methylphenol), 4,4'methylenebis(2,6-di-tert-butylphenol), 4,4'butylidenebis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6tert-butyl-3-methylphenol), and dibutylhydroquinone (DBH).

The specific examples of the ultraviolet absorber are phenol derivatives such as BHT, bisphenol derivatives, arylamines such as condensation products between phenyl-anaphthylamine, phenyl-3-naphthylamine or phenetidine and acetone, and benzophenone compounds.

The compounds of the invention may be used in o admixture with dyes such as allylaminoanthraquinone, 1,4diisopropylamino-anthraquinone, 1,4-diaminoanthraquinone, 20 1,4-dibutyl-aminoanthraquinone, l-amino-4o o anilinoanthraquinone and the like, and perfumes for vaporizable composition.

In supporting the said compounds on a carrier, there can, if necessary, be used additives such as fatty acid esters isopropyl myristate, isopropyl palmitate and hexyl laurate), ana organic solvents isopropyl 0* alcohol and deodorized kerosine) in order to lower the viscosity and facilitate impregnation.

9u e The carrier having the said compounds supported thereon which is obtained in the manner described above can be used by vaporizing the said compounds by mild heating.

It exhibits a high insecticidal and/or acaricidal activity Swhen placed particularly in a relatively closed place, for example, room, storage chamber, closet, warehouse, vehicle, ship, airplane, store, cattle shed, stable, drainage trench, sewer, etc. It permits sufficiently effective control of insects and/or acarines even when placed in an open place, for example, the outdoors.

,6.

-I 3~- ~~^iii I-I n.u 7 9 99 9 94 9 994 99 #9 9 94 9 419 *0 9 9 For heating the carrier having the said compounds supported thereon, there can be utilized surplus or unutilized heat generated by a petroleum benzine pocket heater, a chemically heat-generating pocket heater, a heating element a heater) adjusted to a heating temperature of 500 to 100 0 C, a lighting appliance an electric lamp such as incandescent lamp or fluorescent lamp, or a kerosine lamp). Usually, a commercially available, electric heater for mosquito mat is heated at about 16 0 0C, and a commercially available heater for no mat type device (an insecticidal device in which a part of a porous absorbent wick is immersed in an insecticidal liquid to absorb the insecticidal liquid and its upper part is heated) is heated at approximately 1300 160 0 C. These devices can also be used in the method of the present invention by proper modification of the electric resistance, the material for heat-generating part, adjustment of the thermostat, etc.

Specific examples of application method using a heating element are a method comprising making a carrier into a mat having a suitable size for a heating element, having the said compounds supported on the mat and placing the resulting mat on the heating element, and a method using no mat type device.

As a method utilizing surplus or unutilized heat generated by a pocket heater utilizing heat of chemical reaction, there may be exemplified a method comprising incorporating the said compounds into a heat-generating agent, and a method comprising supporting the said 30 compounds on a wrapping material outside a heat generator.

Specific examples of methods utilizing unutilized heat generated by a lighting appliance an electric lamp such as incandescent lamp or fluorescent lamp, or a kerosine lamp) are a method comprising coating the said compounds on the glass surface of a lamp or a part of a lighting appliance and utilizing heat conducted or emitted by the lamp, and a method comprising placing a carrier having the said compounds supported thereon on or near the glass surface of a lamp and utilizing heat conducted or nA

Z

r

I

2 I- I"- 8 emitted by the lamp.

In the method of the present invention, the application rate of the said compounds is not critical. It should be determined in view of many factors such as the concentration of the compounds, type of preparations, manner and timing of application, environmental temperature and humidity, space to be applied and the width thereof, whether the space is open or not, whether natural or artificial air streams go through the space or not, kind of insects or acarines to be controlled, habitat of insects or acarines, etc. However, the compounds are usually applied in a ratio of from 0.1 mg/m 3 to 50 g/m 3 preferably 1 mg/m 3 to 2 g/m 3 This is only a rough standard and the compounds may be applied beyond the range as occasion demands.

Forming an air stream by stirring the air by artificial wind from a motorized fan an electric fan) or from an air-conditioner or by natural wind may encourage the insecticidal and/or acaricidal efficacy of the method of the present invention so as to enable to apply the 20 method in a wider space.

Compound I can be prepared according to the process disclosed in JP-B-55-42045, for example.

Compound I has optical isomers due to the asymmetric carbon atoms in the alcohol moiety and the acid moiety. It also has geometrical isomers due to the S* cyclopropane ring in the acid moiety. Some of them are o* shown in Table 1. Of the isomers, Compounds [I]-B and show exceptionally higher activity than the other Sisomers isomers.

0 ia 0u 0 Table 1 Symbol of Configuration of Configuration of compound the alcohol the acid moiety moiety S 1R-trans S 1RS-trans RS 1R-trans RS 1RS-cis RS 1RS-cis, trans 6_ 9 The following reference example, preparation examples and test examples serve to give specific illustration of the present invention but they are not intended in any way to limit the scope of the present invention.

Reference Example Compound was prepared as follows: 0.50 Grams of (lS)-l-ethynyl-2-methyl-2-pentenol (described in JP-B-63-52615) was dissolved in dry toluene, and 0.50 g of pyridine was added thereto.

e o o 6 0 0 6 o a *f-lS 1 To the resulting solution was added 0.90 g of (lR)trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride (the corresponding carboxylic acid is described in JP-A-62-253398, for example). The resulting solution was stirred overnight at room temperature. The reaction mixture, after water had been added thereto, was extracted with toluene. The organic layer was washed successively with dilute aqueous hydrochloric acid, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous sodium chloride. Thereafter, the layer was dried over anhydrous sodium sulfate. The dried layer was filtered o and concentrated to obtain a residue. Purify-ng the c 0 o residue with silica gel chromatography (eluent: a 10:1 o 15 mixture of hexane and ethyl acetate) gave 1.05 g of (lS)-l-ethynyl-2-methyl-2-pentenyl (1R)-trans-3-(2,2dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate o0 (Compound in a yield of 83%.

0 Q s 20.5 n 1.5063

D

i 24 [a]D -7.20 (dimethyl ether, C 0.53) o Preparation Example 1 20 In an adequate amount of acetone was dissolved mg of Compound I, and a pulp plate having an area of 4 cm square and a thickness of 0.14 cm was impregnated with the resulting solution. Air-drying the plate to remove acetone therefrom gave a composition capable of vaporizing the active ingredient with mild heating i 4

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V

a a t a ti a ar* aa 1 (hereinafter a mild-heating type vaporizable preparation). Fixing this preparation on the surface of a petroleum benzine pocket heater capable of generating heat of 500 to 70 0 C gave a mild-heating type insecticidal and/or acaricidal device.

Preparation Example 2 In an adequate amount of acetone were dissolved 50 mg of Compound I and 20 mg of BHT, and one side of a nonwoven fabric was impregnated with the 10 resulting solution. Air-drying the nonwoven fabric to remove acetone gave a mild-heating type vaporizable preparation. Using this preparation as an outermost bag of a heat generator capable of generating heat of 500 to 0 C gave a mild-heating type insecticidal and/or acaricidal device.

Preparation Example 3 In an adequate amount of hexane were dissolved 80 mg of Compound 1, 40 mg of octachlorodiisopropyl ether and 30 mg of BHT. Impregnating a pulp plate 20 having an area of 3 cm square and a thickness of 0.1 cm with the resulting solution gave a mild-heating type vaporizable preparation. Attaching this preparation to one side of a pocket heater capable of generating heat of 500 to 70 0 C gave a mild-heating type insecticidal and/or acaridical device.

i aaa% a ii 0+0410 0~0001 a a a 4a a a $0 a 00 o 0.II a'i, Ik( 1 Preparation Example 4 A substrate for electric fumigating mat was prepared by pressing fibrils of a mixture of cotton linter and pulp into a plate having an area of 2.5 cm x 1.5 cm and a thickness of 0.3 cm.

In acetone were dissolved 0.4 g of Compound I and 0.2 g of piperonyl butoxide to make a total volume of 10 ml. Then, the above-prepared mat was uniformly impregnated with 0.5 ml of the resulting solution to obtain a mild-heating type vaporizable preparation.

Fixing this preparation to a heater for electric mat 0 whose heater part was capable of generating heat of 500 to 100 0 C gave a mild-heating type insecticidal and/or o acaricidal device.

Preparation Example In 10 ml of deodorized kerosine was dissolved 100 mg of Compound I to obtain an insecticidal solution.

o The solution was placed in a container. One end of porous absorbent wick having a diameter of 0.9 cm and a length of 7 cm was immersed in the solution and the other end was fixed at the mouth of the container, whereby a mild-heating type vaporizable preparation was obtained. A heater for no-mat type device which was capable of generating heat of 800 to 100 0 C was fixed at the mouth of the container so as to make it possible to heat the upper end of the wick fixed at the mouth of the container. Thus, a mild-heating type insecticidal i LA k3 7

I

4' 00 0 00 0 0* 00 o oso 1 and/or acaricidal device was obtained.

Preparation Example 6 A solution was prepared by uniformly mixing mg of Compound I, 10 mg of 2,2'-methylenebis(6-tertbutyl-4-ethylphenol), 25 mg of isopropyl myristate and mg of kerosine. Uniformly impregnating a substrate for electric fumigating mat having a size of 2.5 cm x cm and a thickness of 0.11 cm (a plate formed of fibril of a mixture of cotton linter and pulp) with this solution gave a mild-heating type vaporizable preparation. Fixing the mat to a heater for electric mat whose heater part was capable of generating heat of 500 to 100 0 C gave a mild-heating type insecticidal and/or acaricidal device.

Preparation Example 7 A transparent vinyl chloride sheet having an area of 50 cm x 9 cm and a thickness of 0.2 cm and containing 500 mg of Compound I uniformly (a mildheating type vaporizable preparation) is wound round and 20 fixed on the surface of a domestic fluorescent lamp (100 V, 20 When the lamp is attached to a domestic fluorescent lighting appliance and an electric current is passed through the lamp, the vinyl chloride sheet is heated by the unutilized heat and functions as a mildheating type insecticidal and/or acaricidal device.

00*3 0 04 0 0 1 C OI 00 0 0 0s 0 *0 i;I t- 1 Preparation Example 8 Into 2 g of diatomaceous earth is infiltrated 0.1 g of Compound I and 0.05 g of BHT to obtain a mildheating type vaporizable preparation. The diatomaceous earth is uniformly incorporated into a heat-generating agent designed to generate heat of 500 to 100°C by utilization of the heat of oxidation. The resulting heat-generating agent is put into a bag made of Japanese paper, whereby a pocket heater having an insecticidal and/or acaricidal function is obtained.

Preparation Example 9 In an adequate amount of acetone are dissolved 50 mg of Compound I, 10 mg of piperonyl butoxide and Set" mg of dibutylhydroquinone. A nonwoven fabric is impregnated with the resulting solution in one side. Airdrying the nonwoven fabric to remove acetone therefrom S' gave a mild-heating type vaporizable preparation. An a. inner bag is made of the thus treated nonwoven fabric and into the inner bag is packed a heat-generating agent o S 20 designed to generate heat of 700 to 100 0 C by utilization of the heat of oxidation. Covering the outside of the 0 o inner bag with a bag made of cotton gave a pocket heater having an insecticidal and/or acaridical function.

In the following test examples, the members tested of Compound I are indicated by the symbols shown in Table 1, and the compounds used for comparison are indicated by the symbols shown in Table 2.

<ix cf Tt 07 1 o oo 00 0 0 00 o 00 00 1 o oo pII 0 0 0 0t 04 0 0 0 01 0 04 Table 2 Symbol of Chemical name Remarks compound (RS)-3-allyl-2-methyl-4- biooxocyclopent-2-enyl allethrin trans-chrysanthemate (RS)-l-ethynyl-2-methyl-2pentenyl (1R)-cis,trans- empenthrin chrysanthemate 2,2-Dichlorovinyl dichorvos dimethylphosphate 1 Test Example 1 A mild-heating type insecticidal and/or acaricidal device (amount of active ingredient: mg/bag) obtained according to Preparation Example 2 was 5 placed in the center of the bottom of a glass chamber of 0.34 m 3 (70 cm cube), and 20 adult houseflies (Musca domestica, CSMA strain) (male/female 1/1) were released in the chamber. In this case, the temperature of heat generator of the mild-heating type insecticidal and/or acaricidal device was 500 to 70 0

C.

After the lapse of 30 minutes, the test insects were transferred to another vessel and given water and diet. After 24 hours, the dead and alive were counted for mortality (two replications).

Table 3 shows the results.

3 "I-;1 d;L~Qi;fl ~aI i__ Table 3 Compound Mortality tested 100 100 100 Untreated 0 1 Test Example 2 The following test was carried out using a 0_n mild-heating type insecticidal and/or acaricidal device (amount of active ingredient: 10 mg/mat) obtained 5 according to Preparation Example 4.

The above device was placed in the center of the bottom of a Peet Grady's chamber of 6.1 m 3 (183 cm cube), in which 50 female adult common mosquitoes (Culex 0000 Spipiens pallens) had been released. Then, an electric o 4 1.3 current was passed through the device so as to adjust the heater temperature to 900 10 0

C.

.r.o The number of knocked-down insects after the 0; a lapse of 10 minutes was counted for percentage of o* o knocked-down insects (two replications).

Table 4 shows the results.

I ,1 w Table 4 Compound Knocked-down tested 100 100 100 4 8 Untreated 0 0 0a 0 t' 1 Test Example 3 oo A mild-heating type insecticidal and/or co acaricidal device (amount of active ingredient: 80 mg/ mat) obtained according to Preparation Example 3 was placed in the center of the bottom of a glass chamber of 0.34 m 3 (70 cm cube).

Two glass Petri dishes (diameter: 9 cm, height: 2 cm) containing 20 adults of Dermatophagoides 4 farinae and diet were placed in diagonal positions at a 0 two corners in the bottom of the glass chamber.

In this case, the temperature of heat Ut 0 CO generator of the mild-heating type insecticidal and/or acaricidal device was 600 10 0

C.

After 120 minutes, the dead and alive were counted for percentage of distressed or dead mites (two replications).

KTO~ o; r i 1 j Table 5 shows the results.

Table Compound Distressed or dead tested 100 100 100 Untreated O en so OS O 0i 000 o00 no,'i o 0f o #1 0 0r 0 0r D 0 0 0 0 0 0 Test Example 4 A mild-heating type insecticidal and/or acaricidal device (amount of active ingredient: 5 100 mg/container) obtained according to Preparation Example 5 was placed in the center of the bottom of a glass chamber of 0.34 m 3 (70 cm cube), and 20 adult German cockroaches (Blattella germanica) (male/female 1/1) were released in the chamber. In this case, the 10 temperature of heating element of the mild-heating type insecticidal and/or acaricidal device was about 100 0

C.

The knocked-down insects after the lapse of minutes was counted for percentage of knocked-down insects (two replications).

Table 6 shows the results.

ii

E

LL i; Table 6 Compound Knocked-down tested 100 100 100 32.5 Untreated 0 0( a1o o 0a 0 01 o 00t 0404 Co., 0 Ot 0I a 1 Test Example The device prepared according to Preparation Example 6 (amount of active ingredient: 50 mg/mat) was placed in the center bottom of a cylinder made of stainless steel having a diameter of 20 cm and a height of 80 cm. An electric current was passed through the device and the temperature of the heater of the device was adjusted to 50 0 C. Ten female adult common mosquitoes (Culex pipiens pallens) were released in a glass tube having a diameter of 4 cm and a height of 12 cm. Then, the both end of the tube were covered with a nylon net of 16 mesh. Thus, the same two tube were prepared. A pedestal was placed in the center top of the above stainless steel cylinder. The glass tubes were placed lengthwise on the pedestal so that the ascending current from the bottom passed through the

C

i

I

1 tubes. 20 Minutes after placing the tubes, the tubes were taken out as they were. To the mosquitoes in the tubes was fed sugared water. 24 Hours later, the dead and alive were counted for mortality.

After the tubes had been taken out, an electric current was continued to pass through the device to keep the temperature of the heater at 50 0

C.

The same test was repeated on 1, 2 and 4 days after the start of passing through of electric current in order to examine the redidual activity.

Table 7 shows the results.

Table 7 0 10 O 0*1 00 011 0044 0 04)~ 0 0I uv0 a Ii C o*7 0~ Li_ Mortality Compound tested Initial after after after nia 1 day 2 days 4 days 100 100 100 100 5 5 5 0 100 100 80 100 25 10 0 Untreated 0 5 0 0

V

21 The superior advantages possessed by the compounds and of the present invention are further illustrated by the following Comparative Test Example.

Comparative Test Example Compounds Used for the Test The compounds used for the Test are listed in Table 8.

Formulations Used for the Test The formulations used for the test were prepared in the same manner as in Preparation Examples 2 and 4 above.

Test Method and the Results Test 1: The same procedure as in Test Example 1 of the present application was repeated. Table 9 shows the results.

Test 2: The same procedure as in Test Example 2 of the present application was repeated. Table 10 shows the result.

a &e o o a 0 a 0 a, a o o o a 8 A~s Li -7 Ta b]I 8 C 2

H

5 eHn 3 CC0 CJI=CCI2 H CH-0-C-CH-CH HC=-C C CH3 CH3 Sybl f Configuration Configuration Symboluof of the alcohol of the acid compund moiety moiety S 1R-trans [Il-B S 1RS-trans RS 1R-trans II]-D RS 1RS--cis [TI-E RS 1RS-cis,trans 4.

a, a 4. 04, a 404 Table 9 Compound Mortality tested M% 100 [Il-B 100 [Il-C 100 [IJ-D [IJ-E Untreated 0 22 r 2 23 Table Compound Knocked-down tested III-A100 (13-B 100 100 [I]-D24 42 Untreated 0 ma o a a o 000 The above data clearly show that compounds and are exceptionally superior to the racemate and the other isomer (cis isomer: a *0 0 a~0. 0 0 4 00 *000

Claims (3)

1. A method for controlling insects and/or acarines comprising vaporizing (iS)-l-ethynyl-2-methyl-2-pentenyl (1R)-trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclo- propanecarboxylate at a temperature which is not higher than 100 0 C and higher than 50 0 C.

2. A method for controlling insects and/or acarines comprising vaporizing (iS)-l-ethynyl-2-methyl-2-pentenyl (1RS)-trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclo- propanecarboxylate at a temperature which is not higher than 100 0 C and higher than 50 0 C.

3. A method for controlling insects and/or acarines comprising vaporizing (lRS)-l-ethynyl-2-methyl-2-pentenyl (1R)-trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclo- s 4 propanecarboxylate at a temperature which is not higher than 100 C and higher than 50 0 C. 006 a* DATED THIS 13TH DAY OF JUNE 13, 1991 SUMITOMO CHEMICAL COMPANY, LIMITED By its Patent Attorneys: .0.000 °GRIFFITH HACK CO. o. 0 a Fellows Institute of Patent Attorneys of Australia. ooRA o 9 0 0 9