Fuming, hot-vaporizing insecticide for killing flies, and method for killing flies with the same

Disclosed is a fuming, hot-vaporizing insecticide for killing flies, which contains propargylfurylmethyl 2,2,3,3-tetramethylcyclopropanecarboxylate of the general formula I: ##STR1## wherein R is hydrogen or methyl, as the active ingredient. The insecticide may be in any form of coil, mat or liquid. Also disclosed is a method of killing flies, using the insecticide.

BACKGROUND OF THE INVENTION 
1. Field of the Invention 
The present invention relates to a fuming, hot-vaporizing insecticide for 
killing flies, which contains as the active ingredient, 
propargylfurylmethyl 2,2,3,3-tetramethylcyclopropanecarboxylate of the 
general formula I: 
##STR2## 
wherein R is hydrogen or methyl, and to a method for killing flies with 
the insecticide. 
2. Prior Art 
As insecticides for repelling and exterminating imaginal mosquitoes, 
popularly used are fuming, hot-vaporizing insecticides in the form of 
mosquitoes-repellent coils, electric mosquitoes-repellent mats and 
electric mosquitoes-repellent liquids. In these days, the breeding of 
mosquitoes is decreasing but there is still a great demand for such 
mosquito repellents. As the active ingredients in them, widely used are 
chrysanthemates, for example 
(.+-.)-2-allyl-3-methyl-cyclopent-2-en-1-on-4-yl (+)-cis, 
trans-chrysanthemate (hereinafter referred to as pynaminforte), its 
stereoisomers such as esbiothrin and esbiol, 
(+)-2-propargyl-3-methyl-cyclopent-2-en-1-on-4-yl, 
(+)-cis,trans-chrysanthemate (hereinafter referred to as etoc), or 
5-propargyl-2-furylmethyl (+)-cis, trans-chrysanthemate (hereinafter 
referred to as furamethrinforte). 
On the other hand, some local areas such as fishing villages, factories for 
processing fishes and shellfishes, plants for garbage disposal, stock 
farming houses, chicken houses and around them are often troubled by flies 
more than before, though the breeding of flies is decreasing in urban 
areas. As the means for eradicating the sources of breeding flies, various 
insecticides such as emulsions, oils and powder preparations are used. In 
addition, space aerosols for repelling and exterminating imaginal flies 
are popular for domestic use, but these have a drawback that the effect 
thereof is often transitory and does not last long. Given the situations, 
a demand for space treating agents of fuming, hot-vaporizing insecticides 
(fuming coils, mats and liquids), of which the effect lasts for several 
hours or more, has become increased. 
Of these, mosquitoes-repellent coils may be lighted from a match to fume in 
a broad space and last long, while the effect thereof is kept constant 
until they are burnt out. Therefore, the means of using them is an 
extremely reasonable insecticidal method. During its use, a 
mosquitoes-repellent coil releases its active ingredients therefrom at its 
part which is remote from the fired part thereof heated at about 
800.degree. C. by several mm and which has been heated at abut 200.degree. 
to 250.degree. C. The diffusibility of the released active ingredients is 
good since the smoke from the fired mosquitoes-repellent coil acts as a 
carrier, so that the coil displays a high insecticidal effect even in an 
open space. On the other hand, regarding mat-type or liquid-type mosquito 
repellents, the temperature of the heater (a hot plate in the mat-type or 
a metal ring in the liquid-type) in the heating and vaporizing device 
fitted in them is from 160.degree. to 180.degree. C. in the mat-type and 
from 120.degree. to 140.degree. C. in the liquid-type, and is lower than 
the temperature at the part of the coil from which its active ingredients 
vaporize, so that the power thereof for vaporizing their active 
ingredients is somewhat poor. However, these types of mosquito repellents 
are suitable for use in closed rooms or in the areas where smoke is not 
accepted. 
First of all, in the process of developping a fuming, hot-vaporizing 
insecticide for killing flies in the form of coil, the present inventor 
tried to use the above-mentioned chrysanthemates that have heretofore been 
used in mosquitoes-repellent coil, mats and the like. However, since the 
effect of pynaminforte or etoc for flies was weak, it was not able to 
obtain a sufficient insecticidal effect even though the concentration of 
the active ingredient in the insecticidal preparation was increased. On 
the other hand, a mosquitoes-repellent coil containing furamethrinforte 
was shown to be effective, but needed to increase further its insecticidal 
effect. In addition it was disadvantageous in point of its cost. Also, in 
a fuming, hot-vaporizing insecticide of mat-type or liquid-type for 
killing flies, pynaminforte and etoc were ineffective even at high 
concentration, though furamethrinforte was effective at high 
concentration. Apart from this, the present inventor selected empenthrin 
which has the highest vapor pressure among commercial pyrethroids, as the 
active ingredient, and has already succeeded in developing a 
flies-repellent coil containing it. However, the coil is disadvantageous 
in point of its cost. In addition, since the compound vaporizes too much, 
a significant loss of the compound is inevitable during the drying step in 
producing coils containing it. In view of these facts, the flies-repellent 
coil was not always satisfactory. Therefore, the selection of the active 
ingredient which is most suitable for a fuming, hot-vaporizing insecticide 
for killing flies was an important theme. 
Accordingly, the object of the present invention is to select an active 
ingredient which is most suitable for a fuming, hot-vaporizing insecticide 
to be used for killing flies in the form of a coil, mat or liquid and to 
provide a fuming, hot-vaporizing insecticide for killing flies which is 
excellent in all the points of insecticidal power, safety, easiness in use 
and producibility as well as a method of killing flies with the 
insecticide. 
In order to solve the above-mentioned problems in the prior art, the 
present inventor tested fuming, hot-vaporizing insecticides containing 
2,2,3,3-tetramethylcyclopropanecarboxylic acid derivative of 
furamethrinforte which was shown to be effective in the preceding test, 
the derivative hereinafter being referred to as tefuramethrin, and he 
admitted that tefuramethrin had a high flies-killing effect, specifically 
considering the fact that the vapor pressure of 
2,2,3,3-tetramethylcyclopropanecarboxylates are higher than one of the 
corresponding chrysanthemate, and that the insecticidal activity of the 
former may be increased when the former is used in the form of a fuming, 
hot-vaporizing insecticide. The present inventor further has made an 
extensive scope of research, and finds that propargyl furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate of the general formula I is 
specifically effective. On the basis of these findings, the inventor has 
completed the present invention. 
That is to say, ester of (+)-2-propargyl-3-methyl-cyclopent-2-en-1-on-4-yl 
or 4-propargylbenzyl alcohol, which is 
2,2,3,3-tetramethylcyclopropanecarboxylate has a low flies-killing effect. 
Therefore, now it is clear that a fuming, hot-vaporizing insecticides with 
a high flies-killing effect is able to be obtained by a combination of 
propargylfurylmethyl alcohol and 2,2,3,3-tetramethylcyclopropanecarboxylic 
acid. 
SUMMARY OF THE INVENTION 
Specifically, the present invention provides a fuming, hot-vaporizing 
insecticide for killing flies, characterized by containing as the active 
ingredient, propargylfurylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate of the general formula I: 
##STR3## 
wherein R is hydrogen or methyl. 
Preferred embodiments of the present invention are as follows: 
A fuming, hot-vaporizing insecticidal coil for killing flies, which 
contains as the active ingredient the ester of the formula I in an amount 
of from 0.3 to 1.2%. 
A fuming, hot-vaporizing insecticidal coil for killing flies, in which the 
active ingredient is 5-propargyl-2-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate. 
A fuming, hot-vaporizing insecticidal coil for killing flies, in which the 
active ingredient is 5-propargyl-2-methyl-3-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate. 
A fuming, hot-vaporizing insecticidal coil for killing flies, which 
additionally contains one or more phenol stabilizers having at least two 
tertiary butyl groups and having a boiling point of 250.degree. C. or 
higher, in an amount of from 0.5 to 3.0 times the content of the active 
ingredient. 
A fuming, hot-vaporizing insecticidal mat for killing flies, which contains 
from 30 to 150 mg of the ester of the formula I as the active ingredient, 
that has been infiltrated into a pulp mat having a thickness of from 1.0 
to 3.0 mm and a surface area of from 7 to 15 cm.sup.2 and which is heated 
on a hot plate in using it so as to vaporize the active ingredient 
therefrom. 
A fuming, hot-vaporizing insecticidal mat for killing flies, in which the 
active ingredient is 5-propargyl-2-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate. 
A fuming, hot-vaporizing insecticidal mat for killing flies, in which the 
active ingredient is 5-propargyl-2-methyl-3-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate. 
A fuming, hot-vaporizing insecticidal mat for killing flies, which 
additionally contains one or more synergists for pyrethroid or esters of 
higher fatty acids, as the vaporization-controlling agent, in an amount of 
from 0.5 to 10 times the content of the active ingredient. 
A fuming, hot-vaporizing insecticidal mat for killing flies, which 
additionally contains one or more phenol stabilizers having at least two 
tertiary butyl groups or hydroquinone stabilizers having at least two 
tertiary butyl groups, in an amount of from 0.1 to 1.0 time the content of 
the active ingredient. 
A fuming, hot-vaporizing insecticidal liquid for killing flies, which 
contains as the active ingredient, the ester of the formula I in an amount 
of from 1 to 6% along with a solvent, the liquid being filled in a plastic 
bottle having therein a liquid-drawing wick, of which wick the lower part 
has been dipped in the liquid and the upper part is heated in using the 
liquid so as to vaporize the active ingredient from the liquid. 
A fuming, hot-vaporizing insecticidal liquid for killing flies, in which 
the active ingredient is 5-propargyl-2-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate. 
A fuming, hot-vaporizing insecticidal liquid for killing flies, in which 
the active ingredient is 5-propargyl-2-methyl-3-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate. 
A fuming, hot-vaporizing insecticidal liquid for killing flies, in which 
the solvent is an aliphatic hydrocarbon having a boiling point of from 
180.degree. to 350.degree. C. 
A fuming, hot-vaporizing insecticidal liquid for killing flies, in which 
the solvent contains water. 
In addition, the present invention also provides a method for killing 
flies, characterized in that a fuming, hot-vaporizing insecticide for 
killing flies, which contains as the active ingredient the ester of the 
formula I, is fumed or hot-vaporized under heat. 
Preferred embodiments of the present invention are as follows: 
A method for killing flies, wherein a fuming, hot-vaporizing insecticidal 
coil for killing flies, which contains as the active ingredient, the ester 
of the formula I in an amount of from 0.3 to 1.2%, is fumed. 
A method for killing flies, wherein a fuming, hot-vaporizing insecticidal 
coil for killing flies, in which the active ingredient is 
5-propargyl-2-furylmethyl 2,2,3,3-tetramethylcyclopropanecarboxylate. 
A method for killing flies, wherein a fuming, hot-vaporizing insecticidal 
coil for killing flies, in which the active ingredient is 
5-propargyl-2-methyl-3-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate. 
A method for killing flies, wherein a fuming, hot-vaporizing insecticidal 
mat for killing flies, which contains from 30 to 150 mg of the ester of 
the formula I as the active ingredient, that has been infiltrated into a 
pulp mat having a thickness of from 1.0 to 3.0 mm and a surface area of 
from 7 to 15 cm.sup.2, is heated on a hot plate so as to vaporize the 
active ingredient therefrom. 
A method for killing flies, wherein a fuming, hot-vaporizing insecticidal 
mat for killing flies, in which the active ingredient is 
5-propargyl-2-furylmethyl 2,2,3,3-tetramethylcyclopropanecarboxylate. 
A method for killing flies, wherein a fuming, hot-vaporizing insecticidal 
mat for killing flies, in which the active ingredient is 
5-propargyl-2-methyl-3-furylmethyl 
2,2,3,3-tetramethylcyclopanecarboxylate. 
A method for killing flies, wherein a fuming, hot-vaporizing insecticidal 
liquid for killing flies, which contains as the active ingredient, the 
ester of the formula I in an amount of from 1 to 6% along with a solvent, 
the liquid being filled in a plastic bottle having therein a 
liquid-drawing wick, of which wick the lower part has been dipped in the 
liquid, is mounted on a heating and vaporizing device, and the upper part 
of the liquid-drawing wick is heated so as to vaporize the active 
ingredient from the liquid. 
A method for killing flies, wherein a fuming, hot-vaporizing insecticidal 
liquid for killing flies, in which the active ingredient is 
5-propargyl-2-furylmethyl 2,2,3,3-tetramethylcyclopropanecarboxylate. 
A method for killing flies, wherein a fuming, hot-vaporizing insecticidal 
liquid for killing flies, in which the active ingredient is 
5-propargyl-2-methyl-3-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate. 
According to the present invention, there is provided a fuming, 
hot-vaporizing insecticide for killing flies, which is effective in 
killing not only mosquitoes but also flies because of the high 
flies-killing activity of the ester compound of the formula I contained 
therein and of the suitable vaporizability of the compound. 
DETAILED DESCRIPTION OF THE INVENTION 
The ester compound of the formula I can be prepared according to the 
conventional synthetic method of ester, by reacting 
2,2,3,3-tetramethylcyclopropanecarboxylic acid or the reactive derivative 
thereof with the propargylfurylmethyl alcohol of the general formula II: 
##STR4## 
wherein R is hydrogen or methyl, or the reactive derivative thereof. 
Examples of the reactive derivative of the carboxylic acid are acid 
halides, acid anhydrides, salts with alkaline metals etc. On the other 
hand, examples of the reactive derivative of the alcohol are halides, etc. 
The reactions may be optionally carried out in suitable solvents. Also the 
reactions may be carried out in the absence or presence of a deoxygenating 
agent or an organic or inorganic base as catalyst. The reactions may be 
achieved at the increased temperature. The reactions may be also carried 
out under an inert atmosphere. 
Among the compounds of the formula I, the following ones are useful for the 
purpose of the invention. Of course, it is possible to use either a single 
compound or a mixture of two or more compounds of the formula I. 
(1) Compound 1 (tefuramethrin): 5-propargyl-2-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate of the formula: 
##STR5## 
(2) Compound 2: 5-propargyl-2-methyl-3-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate of the formula: 
##STR6## 
(3) Compound 3: 5-propargyl-3-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate of the formula: 
##STR7## 
Tefuramethrin has been disclosed in Japanese Patent Publication No. Sho 
46-4196, which has examples of mosquitoes-repellent coils but has no 
technical idea relating to fuming, hot-vaporizing insecticides for killing 
flies. 
The insecticide of the present invention may optionally contain various 
conventional pyrethroids, such as pynamin, pynaminforte, bioallethrin, 
esbiothrin, esbiol, etoc, empenthrin, furamethrin, etc. If desired, it may 
further contain various synergists for pyrethroid such as piperonyl 
butoxide, MGK-264, Synepirin 500, S-421, lethane 384, etc. Microbicides, 
repellents, deodorants, aromatics, etc. may be added to the insecticide of 
the present invention to prepare various fuming, hot-vaporizing 
multi-purpose insecticides for killing flies. 
The fuming, hot-vaporizing insecticidal coil of one embodiment of the 
present invention has a high flies-killing power and is highly 
vaporizable. The content of the ester of the formula I is from 0.3 to 
1.2%, preferably from 0.6 to 1.2%, more preferably from 0.7 to 1.2%. When 
the coil is produced from the ester compound of the formula I with other 
active ingredients such as furamethrin or empenthrin, the total content of 
these active ingredients is preferably from 0.6 to 1.2%, particularly from 
0.7 to 1.2%. 
The coil may be produced by blending the active ingredient and other 
additives (in the amount from 15 to 40% of the total content) suitably 
chosen from among a refuse powder to be obtained by extracting pyrethrum 
flowers, a flaming support such as wood powder, a paste such as powder of 
Machilus thunbergii, starch, dextrin, etc., and optionally adding thereto 
water, a colorant, an antifungal agent, etc., and then treated the 
resulting mixture with the aid of an extruder, molding it into the form of 
coil, and drying the molded coil. Since the ester of the formula I has a 
lower vapor pressure than empenthrin, the loss of the former due to 
vaporization during the drying step in the process of producing the coil 
may be reduced. 
According to the embodiment of the present invention, the coil may contain 
Compound 1 (tefuramethrin) or Compound 2 as the active ingredient, which 
is most useful insecticide among the compounds of the formula I, and 
therefore there is provided a fuming, hot-vaporizing insecticide in the 
form of coil, which has a high flies-killing power. 
In general, pyrethroid compounds themselves including the ester compound of 
the formula I may be stored stably for a long period of time, when blended 
with dibutylhydroxytoluene of from 0 to 0.02 times the content of the 
active ingredient. However, the stability of the compounds in various 
preparations noticeably varies, depending on the kind of the active 
ingredient, and the kind and the amount of the stabilizer to be combined. 
Therefore, the stability of the active ingredients in preparations must be 
evaluated for each active ingredient. 
The stability of the ester compound of the formula I in coils is somewhat 
lower than that of pynaminforte in them. However, when the ester compound 
of the formula I is in the insecticide according to the constitution of 
the present invention containing stabilizers, not only the time-dependent 
stability of the ester of the formula I during storage but also the 
stability thereof during fuming is extremely high, and the ester compound 
of the formula I may display a high flies-killing effect. 
The present inventor investigated various kinds and amounts of stabilizers 
and has found that it is preferred to combine the ester compound of the 
formula I with one or more phenol stabilizers having at least two tertiary 
butyl groups and having a boiling point of 250.degree. C. or higher in an 
amount of from 0.5 to 3.0 times the amount of the ester compound of the 
formula I, while mono-tertiary-butyl-phenol stabilizers such as 
3-tertiary-butyl-4-hydroxyanisole and 2-tertiary-butyl-4-hydroxyanisole 
were ineffective and the effect of amine stabilizers such as 
N,N'-diphenyl-p-phenylenediamine and phenyl-.beta.-naphthylamine was low. 
The reason why the stabilizers having a boiling point of 250.degree. C. or 
higher are effective is considered because the active ingredient the ester 
of the formula I vaporizes at a temperature of abut 200.degree. to 
250.degree. C. so that the stabilizers themselves are needed not to 
vaporize at such temperatures. 
Examples of the stabilizers usable in the present invention are mentioned 
below, which, however, are not limitative. 
(1) 2,6-Di-tertiary-butyl-4-methylphenol (BHT) [Stabilizer A] 
(2) 2,2'-Methylenebis(4-methyl-6-tertiary-butylphenol) [Stabilizer B] 
(3) 2,2'-Methylenebis(4-ethyl-6-tertiary-butylphenol) [Stabilizer C] 
(4) 4,4'-Butylidenebis(3-methyl-6-tertiary-butylphenol) [Stabilizer D] 
(5) 4,4'-Thiobis(3-methyl-6-tertiary-butylphenol) [Stabilizer E] 
(6) 
2-Tertiary-butyl-6-(3-tertiary-butyl-2-hydroxy-5-methylbenzyl)-4-methylphe 
nyl acrylate [Stabilizer F] 
(7) 2,4-Di-Tertiary-butylphenyl 3,5-di-tertiary-butyl-4-hydroxybenzoate 
[Stabilizer G] 
One or more of the above-mentioned stabilizers are added to the ester of 
the formula I in an amount of from 0.5 to 3.0 times the Mount of the 
ester of the formula I. Needless-to-say, other various conventional 
stabilizers such as phosphites, amines and organic sulfur compounds may 
further be added thereto. 
As another embodiment of the present invention, there is provided a fuming, 
hot-vaporizing insecticidal mat for killing flies, which has a high 
flies-killing power. The content of the ester compound of the formula I as 
the active ingredient is from 30 to 150 mg per mat, preferably from 40 to 
150 mg per mat. This may contain, in addition to the active ingredient, 
various ordinary additives of vaporization-controlling agents, 
stabilizers, fragrant agents, dyes, etc. This may be produced by ordinary 
methods. Since the ester of the formula I is more vaporizable than 
pynaminforte and etoc, it is unnecessary to thin the mat of the present 
invention containing the ester of the formula I, and the thickness of the 
mat may be determined freely. 
According to the embodiment of the present invention, the mat may contain 
Compound 1 (tefuramethrin) or Compound 2 as the active ingredient which is 
a useful insecticide among the compounds of the formula I, and therefore 
there is provided a fuming, hot-vaporizing insecticide in the form of mat, 
which has a high flies-killing power. 
According to the embodiment of the present invention, the mat may contain 
one or more synergists for pyrethroid or esters of higher fatty acids as 
the vaporization-controlling agent, and therefore it may stably display 
the flies-killing effect from the start of using it to the end thereof. 
Examples of usable synergists for pyrethroid include N-( 
2-ethylhexyl)-1-isopropyl-4-methyl-bicyclo[2.2.2]oct-5-ene-2,3-dicarboximi 
de (Synepirin 500), N-(2-ethylhexyl)-bicyclo[2.2.1] 
hept-5-ene-2,3-dicarboximide (MGK-264), piperonyl butoxide, etc. Examples 
of usable esters of higher fatty acids include butyl stearate, isopropyl 
myristate, etc. However, these are not limitative. 
Where the mat of the present invention contains stabilizer(s), the 
time-dependent stability of the active ingredient and the dye contained 
therein during storage as well as the stability thereof during heating and 
vaporizing the mat may be enhanced. 
The dye is incorporated into the insecticide of the present invention in 
order to know the amount of the ingredient remained in the insecticide in 
use. Therefore, it is needed not to decolor during storage or use of the 
insecticide. As the phenol stabilizers having at least two tertiary butyl 
groups, preferred are those mentioned above. As usable hydroquinone 
stabilizers having at least two tertiary butyl groups, for example, 
mentioned are di-tertiary-butylhydroquinones such as 
2,5-di-tertiary-butyl-hydroquinone [Stabilizer H]. 
The fuming, hot-vaporizing insecticide for killing flies of the present 
invention may be in the form of a liquid, which does not clog the 
liquid-drawing wick for a long period of time (30 to 60 days) and displays 
the excellent flies-killing activity. The content of the ester compound of 
the formula I as the active ingredient is from 1 to 6%, preferably from 2 
to 6%. The insecticidal liquid of the present invention contains the 
active ingredient and a solvent and optionally contains other additives 
such as fragrant agents, vaporization-controlling agents, stabilizers, 
etc. As the vaporization-controlling agents and stabilizers, those 
mentioned above may be used. 
The plastic bottles into which the liquid is filled and the liquid-drawing 
wicks to be used in the present invention are not specifically defined. 
For example, usable are liquid-drawing wicks formed by solidifying 
inorganic materials with pastes, those formed by burning them, as well as 
those composed of knitted fabrics of felt, cotton or unwoven fabric, or 
glass, inorganic fibers, plastics, woods, porous ceramics or porous 
vaporizable layer, and these are preferably coated with a support of 
glass, inorganic fibers or plastics. 
According to the embodiment of the present invention, the liquid may 
contain as the active ingredient Compound 1 (tefuramethrin) or Compound 2 
which is a useful insecticide among the compounds of the formula I, and 
therefore there is provided a fuming, hot-vaporizing insecticide in the 
form of liquid, which has a high flies-killing power. 
Where the solvents are used at temperatures falling with in the range of 
their boiling point, the active ingredient may well be heated and 
vaporized to display a high flies-killing power while it smells little and 
is toxicologically safe. In particular, aliphatic hydrocarbons such as 
n-paraffins, iso-paraffins and naphthene compounds are preferred as the 
solvents. 
Where water is used as the solvent, it is free from the danger of fire. In 
this case, water is combined with various nonionic surfactants, preferably 
solubilizers of polyoxyalkylene alkyl ethers. ("Solubilizers" indicate 
those capable of stabilizing the active ingredient in water in a clear 
condition, irrespective of their ability of forming micelles, and include 
ordinary surfactants and solvents compatible with both water and oils.) 
According to the method of killing flies of the present invention, the 
fuming, hot-vaporizing insecticide for killing flies, which contains the 
ester of the formula I, is fumed or hot-vaporized under heat to display a 
high flies-killing activity. 
Where the fuming, hot-vaporizing insecticidal coil for killing flies of the 
present invention, which contains the ester of the formula I as the active 
ingredient, is fumed according to the method of the invention, the coil 
may efficiently release and diffuse the active ingredient therefrom and 
its flies-killing activity is extremely high. Therefore, the method is 
extremely effective in killing flies even in a broad space. 
According to the embodiment of the present invention, the coil may contain 
as the active ingredient Compound 1 (tefuramethrin) or Compound 2 which is 
a useful insecticide among the compounds of the formula I, and therefore 
there is provided a method of killing in the form of coil, which has the 
excellent effectiveness in killing flies. 
Where the fuming, hot-vaporizing insecticidal mat for killing flies of the 
present invention, which contains the ester of the formula I as the active 
ingredient, is hot-vaporized under heat according to the method of the 
invention, it is effective in killing flies in closed rooms or in the 
areas where smoke is not accepted. In general, the mat is heated on the 
center of hot plate at 160.degree. to 180.degree. C. 
According to the embodiment of the present invention, the mat may contain 
as the active ingredient Compound 1 (tefuramethrin) or Compound 2 which is 
a useful insecticide among the compounds of the formula I, and therefore 
there is provided a method of killing in the form of mat, which has the 
excellent effectiveness in killing flies. 
Where the fuming, hot-vaporizing insecticidal liquid for killing flies of 
the present invention, which contains the ester of the formula I as the 
active ingredient, is hot-vaporized under heat according to the method of 
the invention, it is effective in killing flies in closed rooms or in the 
areas where smoke is not accepted, for a long period of time (30 to 60 
days). 
In general, the liquid is filled in a heating and vaporizing device having 
therein a liquid-drawing wick, and the device is heated so that the metal 
ring which surrounds the surface of the upper part of the wick may be 
heated at 120.degree. to 140.degree. C. to thereby vaporize the active 
ingredient from the liquid. The structure and the mode of the heating and 
vaporizing device to be used in the present invention are not specifically 
defined, and any popular one may be used freely. 
According to the embodiment of the present invention, the liquid may 
contain as the active ingredient Compound 1 (tefuramethrin) or Compound 2 
which is a useful insecticide among the compounds of the formula I, and 
therefore there is provided a method of killing in the form of liquid, 
which has the excellent effectiveness in killing flies.

Next, the present invention will be explained in more detail by means of 
the following examples and test examples, by which, however, the present 
invention is not restricted. Various changes and modifications of the 
illustrated embodiments can be made therein without departing from the 
spirit and scope of the invention. 
EXAMPLE 1 
0.7 parts of tefuramethrin, 0.7 parts of Stabilizer A 
(2,6-di-tertiary-butyl-4-methylphenol) and 98.6 parts of coil bases such 
as refuse powder to be obtained by extracting pyrethrum flowers, wood 
powder and starch were uniformly blended, kneaded the blend after adding 
water, extruded it and cut it into fuming, hot-vaporizing insecticidal 
coils for killing flies. One coil (13 g) was fumed in a six-mat room (abut 
10 m.sup.2), and the percentage of the active ingredient vaporized was 
measured to be 75%. While it was fumed for 7.5 hours in the room, all the 
flies and mosquitoes therein were repelled or killed. 
EXAMPLE 2 
80 mg of Compound 2 (5-propargyl-2-methyl-3-furylmethyl 
2,2,3,3-tetramethylcyclopropanecarboxylate), 100 mg of Synepirin 500, 10 
mg of Stabilizer H (2,5-di-tertiary-butylhydroquinone) and 0.6 mg of a dye 
of diisopropylaminoanthraquinone were infiltrated into a pulp mat having a 
thickness of 2.8 mm, a length of 22 mm and a width of 35 mm, to obtain a 
fuming, hot-vaporizing insecticidal mat for killing flies. This mat was 
packed in an aluminium film bag and stored at room temperature for 3 
years. The bag was opened and the mat was taken out therefrom, and the mat 
was mounted on the hot plate (in the center part at about 170.degree. C.) 
in a heating and vaporizing device and used in a closed room. This was 
effective against not only mosquitoes but also flies for a period of 12 
hours. With the lapse of time of using it, the dye was faded in an 
ordinary manner. The stability of both Compound 2 and the dye during 
storage was good. 
EXAMPLE 3 
45 ml of an n-paraffin solution containing 5% of tefuramethrin was filled 
in a 50 ml-plastic bottle, and a liquid-drawing wick (outer diameter 7.0 
mm, length 75.5 mm) provided with a holder was inserted thereinto. As the 
liquid-drawing wick, used was a bundle of polyester fibers covered with a 
knitted fabric made of polyester fibers and coated with a silicone 
varnish. The upper surface of the wick was heat-sealed. The n-paraffin 
used had a boiling point of from 250.degree. to 280.degree. C. The fuming, 
hot-vaporizing insecticidal liquid for killing flies, thus obtained, was 
mounted on a heating and vaporizing device, to which an electric current 
was applied so that the metal ring which surrounds the surface of the top 
of the liquid-drawing wick might be heated at 130.degree. C. The amount of 
the liquid vaporized under heat was about 1.5 ml/day (used for 12 days in 
one day) for 30 days. During the period, the wick was not clogged, and the 
liquid maintained a high flies-killing activity. 
Test Example 1 
According to Example 1, fuming, hot-vaporizing insecticidal coil samples 
for killing flies were prepared, each having the formulation shown in 
Table 1. The time-dependent stability of these (when stored at 25.degree. 
C. for 2 years) and the insecticidal activity thereof for killing imaginal 
flies according to the cylindrical method mentioned below were tested. The 
coil samples contained, in addition to the ingredients shown in Table 1, 
28% by weight of starch, 0.2% by weight of sodium dehydroacetate, 25% by 
weight of refuse powder obtained by extracting pyrethrum flowers, and a 
balance of wood powder to make 100% by weight in total. The time-dependent 
stability of these samples was evaluated on the basis of the criteria 
mentioned below. The flies-killing activity thereof was represented by a 
relative value based on the knockdown activity (1.0) of a standard coil 
sample containing 1.0% by weight of empenthrin. Stabilizers A, B, C and F 
used in this test are those mentioned hereinabove. 
Criteria for Time-dependent Stability: 
.smallcircle.: The recovery of the active ingredient after stored for 2 
years at 25.degree. was more than 95%. 
.DELTA.: The recovery of the active ingredient after stored for 2 years at 
25.degree. C. was from 90 to 95%. 
.times.: The recovery of the active ingredient after stored for 2 years at 
25.degree. C. was less than 90%. 
Cylindrical Method: 
A plastic cylinder having an inner diameter of 20 cm and a height of 43 cm 
was placed on a table having a height of 30 cm. The cylinder had glass 
disks through rubber gaskets at the top and at the bottom thereof, and the 
glass disk at the bottom had a hole of 5 cm diameter in the center. About 
20 flies were allowed to fly in the cylinder, while was entered a coil 
lighted at one end from the hole of the disk at the bottom, and fumed for 
two minutes. After fuming, the number of the knockdown flies was counted 
with the lapse of time, and the KT.sub.50 value was calculated. 
TABLE 1 
__________________________________________________________________________ 
Formulation (wt. %) Time-dependent Loss of Active 
Active Ingredients Stability ingredients 
Compound of the 
Other during Flies-killing 
during 
Formula I Ingredient 
Stabilizer 
Storage Activity 
Production 
__________________________________________________________________________ 
Samples of the 
1 
Tefuramethrin 
0.6 
-- A 0.9 
.largecircle. 
1.0 Negligible 
Invention 
2 
Tefuramethrin 
0.7 
-- A 1.0 
.largecircle. 
1.1 Negligible 
3 
Tefuramethrin 
0.8 
-- -- .DELTA. 0.8 Negligible 
4 
Tefuramethrin 
0.8 
-- A 0.3 
.DELTA. 0.9 Negligible 
5 
Tefuramethrin 
0.8 
-- A 0.5 
.largecircle. 
1.3 Negligible 
6 
Tefuramethrin 
0.8 
-- A 1.2 
.largecircle. 
1.3 Negligible 
7 
Tefuramethrin 
0.8 
-- A 2.0 
.largecircle. 
1.3 Negligible 
8 
Tefuramethrin 
0.8 
-- A 2.7 
.largecircle. 
1.2 Negligible 
9 
Tefuramethrin 
1.2 
-- A 1.2 
.largecircle. 
1.4 Negligible 
10 
Compound 2 
0.6 
-- A 0.9 
.largecircle. 
1.0 Negligible 
11 
Compound 2 
0.7 
-- A 1.0 
.largecircle. 
1.1 Negligible 
12 
Compound 2 
0.8 
-- A 0.3 
.DELTA. 0.9 Negligible 
13 
Compound 2 
0.8 
-- A 1.2 
.largecircle. 
1.3 Negligible 
14 
Compound 2 
0.8 
-- A 2.4 
.largecircle. 
1.3 Negligible 
15 
Compound 2 
1.2 
-- A 1.2 
.largecircle. 
1.4 Negligible 
16 
Compound 3 
0.6 
-- A 0.9 
.largecircle. 
1.0 Negligible 
17 
Compound 3 
0.7 
-- A 1.0 
.largecircle. 
1.0 Negligible 
18 
Compound 3 
0.8 
-- A 0.3 
.DELTA. 0.8 Negligible 
19 
Compound 3 
0.8 
-- A 1.2 
.largecircle. 
1.2 Negligible 
20 
Compound 3 
1.2 
-- A 1.2 
.largecircle. 
1.3 Negligible 
21 
Tefuramethrin 
0.3 
Furamethrin.sup.1) 
0.4 
C 0.25 
.largecircle. 
1.1 Negligible 
F .sup. 0.45 
22 
Tefuramethrin 
0.3 
Empenthrin 
0.3 
A 0.4 
.largecircle. 
1.0 Slight 
B .sup. 0.3 
Control 1 
-- Pynaminforte 
0.8 
-- .largecircle. 
0.5 Negligible 
Samples 2 
-- Pynaminforte 
0.8 
A 0.4 
.largecircle. 
0.5 Negligible 
3 
-- Compound 4.sup.2) 
0.8 
A 0.4 
.largecircle. 
0.5 Negligible 
4 
-- Compound 5.sup.3) 
0.8 
A 0.4 
.largecircle. 
0.4 Negligible 
5 
-- Empenthrin 
1.0 
A 0.2 
.largecircle. 
1.0 Large 
__________________________________________________________________________ 
.sup.1) Furamethrin: Its acid moiety is dtrans form. 
.sup.2) Compound 4: (+)2-propargyl-3-methyl-cyclopent-2-en-1-on-4-yl 
2,2,3,3tetramethylcyclopropanecarboxylate. 
.sup.3) Compound 5: 4propargylbenzyl 
2,2,3,3tetramethylcyclopropanecarboxylate. 
The test results verify the following facts: The fuming, hot-vaporizing 
insecticidal coil samples for killing flies, which contained 
tefuramethrin, Compound 2 or Compound 3, had a higher flies-killing 
activity than the control pynaminforte-containing coil samples. By adding 
phenol stabilizers having at least two tertiary butyl groups to the 
samples in an amount of 0.5 times or more the amount of the ester of the 
formula I, the time-dependent stability of the ester of the formula I in 
the samples was improved so that the flies-killing effect of the samples 
being fumed was increased. Coils containing 0.3% of pynaminforte were 
effective against mosquitoes, while those containing 0.8% of pynaminforte 
were poorly effective against flies. The stabilizer incorporated into the 
pynaminforte-containing coils was almost ineffective in stabilizing the 
pynaminforte therein. Further, 2,2,3,3-tetramethylcyclopropanecarboxylate 
in which the alcohol is (+)-2-propargyl-3-methylcyclopent-2-en-1-on-4-yl 
or 4-propargylbenzyl alcohol had a low flies-killing effect. As opposed to 
these, it was preferred to incorporate particular stabilizer(s) to coils 
containing the ester compound of the formula I, and the coils containing 
such stabilizer(s) had a higher flies-killing activity. Accordingly, the 
practical utility of these coils is extremely high. The control 
empenthrin-containing coil was too much vaporizable, and the loss of the 
active ingredient during the drying step in the process of producing it 
was disadvantageously large. However, the time-dependent stability of the 
coil during storage was good. 
Test Example 2 
According to Example 2, fuming, hot-vaporizing insecticidal mat samples for 
killing flies were prepared, each having the formulation shown in Table 2. 
Using a heating and vaporizing device where the temperature of the center 
part of the hot plate was about 168.degree. C., the flies-killing activity 
of these samples was evaluated according to the continuous aeration method 
mentioned below. The results obtained are shown in Table 2. Meanwhile, the 
time dependent stability was evaluated according to the criteria in Test 
Example 1, and the flies-killing activity was represented by a relative 
value based on the knockdown effect (1.0) of a standard coil sample 
containing 1.0% by weight of empenthrin. 
Continuous Aeration Method: 
Two plastic cylinders each having an inner diameter of 20 cm and a height 
of 43 cm were placed one upon another, and a cylinder having an inner 
diameter of 20 cm and a height of 20 cm and having therein a 16-mesh wire 
gauze to partition its inner space into two (flies are put in the upper 
space thus partitioned) was placed on the upper plastic cylinder. In 
addition, another cylinder having the same diameter and a height of 20 cm 
was placed on the third cylinder. The four-stage cylinder kit was mounted 
on a table, while the heating and vaporizing device having therein the mat 
sample was set in the center of the table. In this way, the mat was heated 
and vaporized. About 20 flies were allowed to fly in the upper cylinder, 
whereupon the number of the knockdown flies was counted with the lapse of 
time. Twenty minutes after the exposure of the flies to the vapor from the 
mat, all the flies were transferred into a clean polyethylene container, 
and 3% aqueous sugar solution was applied thereto. After 24 hours, the 
number of the killed flies was counted, from which the percentage of the 
killed flies was obtained. 
TABLE 2 
__________________________________________________________________________ 
Formulation (mg/mat) Time dependent 
Flies-killing 
Active Ingredients Stability 
Activity.sup.1) 
Compound of the 
Other Vaporization- during After 
After Six 
Formula I Ingredient 
controlling Agent 
Stabilizer 
Storage Hour Hours 
__________________________________________________________________________ 
Samples of 
1 
Tefuramethrin 
30 -- Synepirin 500 
H 10 .largecircle. 
1.0 0.6 
the Invention 100 (95) (70) 
2 
Tefuramethrin 
40 -- Synepirin 500 
H 10 .largecircle. 
1.0 0.7 
100 (100) (75) 
3 
Compound 2 
40 -- Synepirin 500 
H 10 .largecircle. 
1.0 0.7 
100 (100) (75) 
4 
Tefuramethrin 
60 -- Synepirin 500 
H 10 .largecircle. 
1.1 0.8 
100 (100) (80) 
5 
Tefuramethrin 
80 -- -- -- .DELTA. 1.4 0.6 
(100) (75) 
6 
Tefuramethrin 
80 -- -- H 10 .largecircle. 
1.4 0.7 
(100) (75) 
7 
Tefuramethrin 
80 -- Synepirin 500 
H 10 .largecircle. 
1.3 0.8 
40 (100) (85) 
8 
Tefuramethrin 
80 -- Synepirin 500 
H 10 .largecircle. 
1.1 0.9 
100 (100) (85) 
9 
Tefuramethrin 
80 -- Synepirin 500 
H 10 .largecircle. 
1.1 1.0 
600 (100) (95) 
10 
Tefuramethrin 
80 -- Synepirin 500 
-- .DELTA. 1.1 0.8 
100 (100) (85) 
11 
Tefuramethrin 
80 -- Synepirin 500 
A 40 .largecircle. 
1.1 0.9 
100 (100) (90) 
12 
Tefuramethrin 
80 -- Synepirin 500 
A 80 .largecircle. 
1.1 0.9 
100 (100) (90) 
13 
Tefuramethrin 
150 
-- Synepirin 500 
H 15 .largecircle. 
1.3 1.0 
100 (100) (95) 
14 
Compound 2 
60 -- Synepirin 500 
H 10 .largecircle. 
1.1 0.8 
100 (100) (80) 
15 
Compound 2 
80 -- -- -- .DELTA. 1.4 0.6 
(100) (75) 
16 
Compound 2 
80 -- -- H 10 .largecircle. 
1.4 0.7 
(100) (75) 
17 
Compound 2 
80 -- Synepirin 500 
-- .DELTA. 1.1 0.8 
100 (100) (85) 
18 
Compound 2 
80 -- Synepirin 500 
H 10 .largecircle. 
1.1 0.9 
100 (100) (85) 
19 
Compound 2 
150 
-- Synepirin 500 
H 15 .largecircle. 
1.3 0.9 
100 (100) (95) 
20 
Compound 3 
60 -- Isopropyl 
H 10 .largecircle. 
1.1 0.7 
Myristate (100) (80) 
100 
21 
Compound 3 
80 -- -- -- .DELTA. 1.4 0.6 
(100) (70) 
22 
COmpound 3 
80 -- -- H 10 .largecircle. 
1.4 0.7 
(100) (75) 
23 
Compound 3 
80 -- Synepirin 500 
-- .DELTA. 1.0 0.7 
100 (100) (80) 
24 
Compound 3 
80 -- Synepirin 500 
H 10 .largecircle. 
1.1 0.8 
100 (100) (90) 
25 
Compound 3 
150 
-- Isopropyl 
H 15 .largecircle. 
1.2 0.8 
Myristate (100) (90) 
100 
26 
Tefuramethrin 
40 -- Synepirin 500 
H 10 .largecircle. 
1.1 0.9 
Compound 2 
40 100 (100) (90) 
Control 
1 
-- Pynaminforte 
60 Isopropyl 
A 40 .largecircle. 
0.4 0.5 
Samples Myristate (65) (70) 
10 
2 
-- Pynaminforte 
150 
Isopropyl 
A 40 .largecircle. 
0.5 0.5 
Myristate (70) (75) 
15 
3 
-- Etoc 60 Isopropyl 
A 40 .largecircle. 
0.5 0.5 
Myristate (75) (75) 
35 
4 
-- Etoc 150 
Isopropyl 
A 40 .largecircle. 
0.5 0.5 
Myristate (75) (75) 
80 
5 
-- Compound 6.sup.2) 
80 Synepirin 500 
A 40 .largecircle. 
0.5 0.5 
100 (75) (75) 
__________________________________________________________________________ 
.sup.1) Flieskilling Activity: This means a relative value based on the 
knockdown effect (1.0) of a standard coil sample containing 1.0% by weigh 
of empenthrin. The parenthesized value indicates the percentage of the 
killed flies. 
.sup.2) Compound 6: (.+-.)2-allyl-3-methyl-cyclopent-2-en-1-on-4-yl 
2,2,3,3tetramethylcyclopropanecarboxylate. 
The test results verify the following facts: The fuming, hot-vaporizing 
insecticidal mat samples for killing flies, which contained tefuramethrin, 
Compound 2 or Compound 3 which is the ester compound of the formula I, had 
a higher knockdown activity and a higher flies-killing activity than the 
control pynaminforte-containing or etoc-containing mat samples. Mats 
containing from 10 mg to 40 mg of pynaminforte or etoc were effective 
against mosquitoes, while those containing 150 mg of the active ingredient 
(pynaminforte or etoc) were ineffective against flies. Practical use of 
the latter is difficult. In particular, the knockdown effect of the latter 
was poor. Since pynaminforte and etoc have a lower vapor pressure than the 
ester compound of the formula I, the increase in the content of the former 
in the mat does not always result in the increase in the vapor of the 
active ingredient to be emitted from the mat but will merely result in the 
increase in the amount of the non-used residue of the mat. Esters of 
(.+-.)-2-allyl-3-methyl-cyclopent-2-en-1-on-4-ol which is 
2,2,3,3-tetramethyl-cyclopropanecarboxylate had a low flies-killing 
effect. Therefore, now it is clear that a fuming, hot-vaporizing 
insecticides with a high flies-killing effect is able to be obtained by 
the ester of propargylfurylmethyl alcohol and 
2,2,3,3-tetramethyl-cyclopropanecarboxylic acid. In order to increase the 
amount of the vapor of the control active ingredient (pynaminforte or 
etoc) to be emitted from the control mats, the thickness of the control 
mats was reduced to 1 mm (the thickness of the mats tested in this test 
was 2.8 mm) and these were again tested. However, the effect of these thin 
mats did not almost improved. 
Test Example 3 
According to Example 3, fuming, hot-vaporizing insecticidal liquid samples 
for killing flies were prepared, each having the formulation shown in 
Table 3. Each sample was put in a bottle set in a heating and vaporizing 
device. The metal ring in the device was heated to about 132.degree. C. so 
that the top of the liquid-drawing wick in the bottle might be heated. The 
flies-killing activity of these samples was evaluated according to the 
continuous aeration method mentioned in Test Example 2. The results 
obtained are shown in Table 3. 
TABLE 3 
__________________________________________________________________________ 
Formulation (%) Flies-killing 
Active Ingredients Activity.sup.1) 
Compound of the 
Other After 
After 
Formula I Ingredient 
Solvent 
One Day 
Thirty Days 
__________________________________________________________________________ 
Samples of the 
1 Tefuramethrin 
1.0 
-- n-Paraffin 
1.0 0.9 
Invention (90) (90) 
2 Tefuramethrin 
2.0 
-- Water 1.1 1.0 
(95) (95) 
3 Compound 2 
2.0 
-- n-Paraffin 
1.1 1.0 
(95) (90) 
4 Tefuramethrin 
3.0 
-- n-Paraffin 
1.2 1.0 
(98) (95) 
5 Tefuramethrin 
5.0 
-- n-Paraffin 
1.3 1.2 
(100) 
(98) 
6 Tefuramethrin 
6.0 
-- n-Paraffin 
1.4 1.3 
(100) 
(95) 
7 Tefuramethrin 
3.0 
-- Water 1.3 1.1 
(98) (96) 
8 Compound 2 
3.0 
-- n-Paraffin 
1.2 1.0 
(98) (95) 
9 Compound 2 
5.0 
-- n-Paraffin 
1.3 1.2 
(100) 
(95) 
10 Compound 2 
3.0 
-- Water 1.3 1.5 
(95) (95) 
11 Compound 3 
3.0 
-- n-Paraffin 
1.1 1.0 
(95) (90) 
12 Compound 3 
5.0 
-- n-Paraffin 
1.2 1.1 
(95) (90) 
13 Compound 3 
3.0 
-- Water 1.2 1.1 
(95) (95) 
Control 1 -- Pynaminforte 
3.0 
n-Paraffin 
0.4 0.3 
Samples (0) (0) 
2 -- Pynaminforte 
6.0 
n-Paraffin 
0.5 0.4 
(0) (0) 
3 -- Etoc 3.0 
n-Paraffin 
0.8 0.6 
(10) (10) 
4 -- Etoc 6.0 
n-Paraffin 
0.9 0.8 
(10) (15) 
__________________________________________________________________________ 
.sup.1) Flieskilling Activity: This means a relative value based on the 
knockdown effect (1.0) of a standard coil sample containing 1.0% by weigh 
of empenthrin. The parenthesized value indicates the percentage of the 
killed flies. 
The test results verify the following facts: The fuming, hot-vaporizing 
insecticidal liquid samples for killing flies, which contained 
tefuramethrin, Compound 2 or Compound 3 which is the ester compound of the 
formula I, had a higher knockdown activity and a higher flies-killing 
activity than the control pynaminforte-containing or etoc-containing 
liquid samples. Liquids containing from 2.6% of pynaminforte or containing 
from 0.7 to 1.3% of etoc were effective against mosquitoes, while the 
knockdown effect of those containing 6% of the active ingredient 
(pynaminforte or etoc) was poor and the flies-killing effect of them was 
extremely low. Therefore, it was almost impossible to expect the practical 
use of the liquids containing pynaminforte or etoc. The increase in the 
concentration of pynaminforte or etoc in the liquids caused clogging of 
the liquid-drawing wick during use and was therefore not practicable. 
These facts support the practical usefulness of the fuming, hot-vaporizing 
insecticidal liquids for killing flies, which contain the ester of the 
formula I. 
As has been explained in detail in the above, the fuming, hot-vaporizing 
insecticide for killing flies of the present invention, which contains the 
ester of the formula I as the active ingredient, have various advantages. 
Specifically, the invention of claim 1 provides a fuming, hot-vaporizing 
insecticide for killing flies, which is satisfactorily effective against 
not only mosquitoes but also flies, which is safe and is used with ease 
and which is produced efficiently. 
The invention of claims 2 to 4 provides a fuming, hot-vaporizing 
insecticidal coil for killing flies, which has a high flies-killing 
activity and which efficiently releases and diffuses the active ingredient 
therefrom. 
The invention of claim 5 provides a fuming, hot-vaporizing insecticidal 
coil for killing flies, of which not only the time-dependent stability 
during storage but also the stability during fuming it has been enhanced. 
The invention of claims 6 to 8 provides a fuming, hot-vaporizing 
insecticidal mat for killing flies, which has an excellent flies-killing 
activity. 
The invention of claim 9 provides a fuming, hot-vaporizing insecticidal mat 
for killing flies, which stably maintains its flies-killing activity from 
the start of using it to the end thereof. 
The invention of claim 10 provides a fuming, hot-vaporizing insecticidal 
mat for killing flies, which has an improved time-dependent stability of 
the active ingredient and the dye contained therein during storage and has 
an improved stability of itself when the mat is heated and vaporized. 
The invention of claims 11 to 13 provides a fuming, hot-vaporizing 
insecticidal liquid for killing flies, which displays an excellent 
flies-killing activity for a long period of time (30 to 60 days) without 
causing clogging of the liquid-drawing wick used. 
The invention of claim 14 provides a fuming, hot-vaporizing insecticidal 
liquid for killing flies, which has a high flies-killing power and which 
emits little odor and is therefore toxicologically safe. 
The invention of claim 15 provides a fuming, hot-vaporizing insecticidal 
liquid for killing flies, which is free from the danger of fire. 
The invention of claim 16 provides a method for killing flies, which uses 
the ester of the formula I as the active ingredient and is effective in 
killing not only mosquitoes but also flies. 
The invention of claims 17 to 19 provides a method for killing flies, where 
a fuming, hot-vaporizing insecticidal coil for killing flies is fumed to 
display an excellent flies-killing activity. The vapor of the active 
ingredient to be generated by fuming the coil diffuses well, and the 
method is effective in killing flies in a broad space. 
The invention of claims 20 to 22 provides a method for killing flies, where 
a fuming, hot-vaporizing insecticidal mat for killing flies is heated and 
vaporized to display an excellent flies-killing activity. The method is 
especially suitable for killing flies in closed rooms or in the areas 
where smoke is not accepted. 
The invention of claims 23 to 25 provides a method for killing flies, where 
a fuming, hot-vaporizing insecticidal liquid for killing flies is heated 
and vaporized to display an excellent flies-killing activity. Since the 
flies-killing activity of the liquid lasts long (30 to 60 days), this 
method is especially suitable for killing flies in closed rooms or in the 
areas where smoke is not accepted, for a long period of time. 
While the invention has been described in detail and with reference to 
specific embodiments thereof, it will be apparent to one skilled in the 
art that various changes and modifications can be made therein without 
departing from the spirit and scope thereof.