A bromodichloroimidazole derivative represented by the formula ##STR1## wherein R represents a C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 alkyl substituted by one or more halogen atoms, C.sub.3 alkenyl, C.sub.3 alkenyl substituted by one or more halogen atoms, C.sub.3 alkynyl or C.sub.3 alkynyl group substituted by one or more halogen atoms; its production; and an insecticidal and/or acaricidal composition containing it as an active ingredient.

The present invention relates to a bromodichloroimidazole derivative 
represented by the formula (I) (hereinafter referred to as present 
compound), 
##STR2## 
wherein R represents a C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 alkyl 
substituted by one or more halogen atoms (e.g. chlorine, bromine, iodine 
and fluorine), C.sub.3 alkenyl, C.sub.3 alkenyl substituted by one or more 
halogen atoms (e.g. chlorine, bromine, iodine and fluorine), C.sub.3 
alkynyl or C.sub.3 alkynyl group substituted by one or more halogen atoms 
(e.g. chlorine, bromine, iodine and fluorine), its production and an 
insecticidal and/or acaricidal composition containing it as an active 
ingredient. 
It is described in B.P. No. 1,316,665, U.S. Pat. No. 3,674,874, etc. that a 
certain kind of trihaloimidazole derivative, for example 
1-n-pentyloxymethyl-2,4,5-trichloroimidazole, 
1-isopropoxymethyl-2,4,5-trichloroimidazole, etc., can be used as an 
active ingredient for insecticidal and/or acaricidal compositions. It may 
not always be said, however, that these compounds are always satisfactory 
as such active ingredient. 
The present inventors extensively studied to find a compound having a more 
superior insecticidal and/or acaricidal activity, and as a result, found 
that the present compound represented by the formula (I) has excellent 
properties as follows: 
1. Insecticidal and/or acaricidal activity is very high. 
2. Activity against cockroaches is particularly high. 
3. Activity against insecticide resistant colony is also high. 
4. Effect as fumigants is high. 
The present inventors thus completed the present invention. 
The present compound has particularly a high activity against cockroaches 
such as German cockroach (Blattella germanica), American cockroach 
(Periplaneta americana), smoky brown cockroach (Periplaneta fuliginosa), 
etc. 
The present compound, therefore, can be used as an active ingredient for 
insecticidal and/or acaricidal compositions which display an effect on 
insect pests in question in many scenes. Particularly, it is expected to 
be used as an active ingredient for cockroach-controlling fumigants. 
In the present compound represented by the formula (I), preferred compounds 
are those in which R is a C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkyl 
substituted by one or more halogen atoms, C.sub.3 alkenyl or C.sub.3 
alkynyl group, and more preferred ones include: 
1-methoxymethyl-2-bromo-4,5-dichloroimidazole, 
1-n-propyloxymethyl-2-bromo-4,5-dichloroimidazole, 
1-isopropyloxymethyl-2-bromo-4,5-dichloroimidazole, 
1-(4-bromobutyloxymethyl)-2-bromo-4,5-dichloroimidazole, 
1-(4-chlorobutyloxymethyl)-2-bromo-4,5-dichloroimidazole, etc. 
As a compound for cockroach-controlling fumigants, 
1-(4-bromobutyloxymethyl)-2-bromo-4,5-dichloroimidazole is particularly 
preferred. 
The present compounds can be produced by reacting 
2-bromo-4,5-dichloroimidazole with a halomethyl ether represented by the 
formula (II), 
EQU XCH.sub.2 --OR (II) 
wherein X represents a halogen atom (e.g. chlorine and bromine), and R has 
the same meaning as described above, at about 0.degree. C. to about 
150.degree. C. for about 1 to about 24 hours in a solvent in the presence 
of a dehydrohalogenating agent. 
The present compounds can also be produced by reacting a 
halomethylbromodichloroimidazole represented by the formula (III), 
##STR3## 
wherein Y represents a halogen atom (e.g. chlorine, bromine), with an 
alcohol represented by the formula (IV), 
EQU HOR (IV) 
wherein R has the same meaning as described above, at about 0.degree. C. to 
about 150.degree. C. for about 1 to about 24 hours in a solvent in the 
presence of a dehydrohalogenating agent. 
The solvent used in this reaction includes for example aliphatic 
hydrocarbons (e.g. hexane, heptane, ligroin, petroleum ether), aromatic 
hydrocarbons (e.g. benzene, toluene, xylene), halogenated hydrocarbons 
(e.g. chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, 
dichlorobenzene), ethers (e.g. diethyl ether, diisopropyl ether, dioxane, 
tetrahydrofuran, ethylene glycol dimethyl ether), ketones (e.g. acetone, 
methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone), 
alcohols (e.g. methanol, ethanol, propanol, butanol, allyl alcohol, 
propargyl alcohol), esters (e.g. ethyl formate, ethyl acetate, butyl 
acetate, diethyl carbonate), nitro compounds (e.g. nitroethane, 
nitrobenzene), nitriles (e.g. acetonitrile, isobutyronitrile), tertiary 
amines (e.g. pyridine, triethylamine, N,N-diethylaniline, tributylamine, 
N-methylmorpholine), acid amides (e.g. formamide, N,N-dimethylformamide, 
N,N-dimethylacetamide), sulfur compounds (e.g. dimethyl sulfoxide, 
sulfolane) and mixtures thereof. 
The dehydrohalogenating agent includes for example organic bases (e.g. 
pyridine, triethylamine, N,N-diethylaniline), inorganic bases (e.g. sodium 
hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, 
sodium hydride), alkali metal alkoxides (e.g. sodium methoxide, sodium 
ethoxide) and the like. 
After completion of the reaction, the usual after-treatment is applied, and 
if necessary, purification by chromatography, distillation, 
recrystallization, etc. may be applied. 
2-Bromo-4,5-dichloroimidazole, a starting material for the present 
compounds, can be produced, for example, by a method described in U.S. 
Pat. No. 3,409,606 and J. Heterocycl. Chem., 399 (1967).

Production examples for the present compounds will be shown. 
PRODUCTION EXAMPLE 1 
To a solution of 0.86 g of 2-bromo-4,5-dichloroimidazole in 5 ml of 
dimethylformamide was added 96 mg of sodium hydride at room temperature, 
and after standing for 30 minutes, 0.32 g of methoxymethyl chloride was 
added dropwise. The resulting mixture was stirred at room temperature for 
1 hour, and after adding 40 ml of water, extracted with 30 ml of diethyl 
ether. Extraction with diethyl ether was repeated two more times, and the 
ether extract was dried over magnesium sulfate and concentrated to obtain 
an oily product. This product was purified by column chromatography on 
silica gel to obtain 0.40 g of 
1-methoxymethyl-2-bromo-4,5-dichloroimidazole. 
EQU n.sub.D.sup.26 1.5402 
PRODUCTION EXAMPLE 2 
A mixture of 1.06 g of 1-chloromethyl-2-bromo-4,5-dichloroimidazole, 0.54 g 
of sodium ethoxide and 40 ml of ethanol was heated under reflux for 10 
hours. The reaction mixture was then concentrated under reduced pressure 
to obtain an oily product. This product was purified by column 
chromatography on silica gel to obtain 0.25 g of 
1-ethoxymethyl-2-bromo-4,5-dichloroimidazole. 
EQU n.sub.D.sup.26 1.5296 
PRODUCTION EXAMPLE 3 
To a mixture of 1.08 g of 2-bromo-4,5-dichloroimidazole, 0.51 g of 
triethylamine and about 30 ml of toluene was added dropwise 0.79 g of 
4-chlorobutoxymethyl chloride at room temperature, and the resulting 
mixture was stirred at room temperature for 2 hours. The deposited crystal 
was filtered off and washed with about 10 ml of toluene. The filtrate thus 
obtained was concentrated under reduced pressure, and the residual oily 
product was purified by column chromatography on silica gel to obtain 0.60 
g of 1-(4-chlorobutoxymethyl)-2-bromo-4,5-dichloroimidazole. 
EQU n.sub.D.sup.28 1.5302 
Some of the present compounds which can be produced by these methods will 
be shown in Table 1. 
TABLE 1 
______________________________________ 
Bromodichloroimidazole derivatives represented by the formula, 
##STR4## 
Compound Physical 
No. R constant 
______________________________________ 
(1) CH.sub.3 n.sub.D.sup.26 1.5402 
(2) CH.sub.2 CH.sub.3 n.sub.D.sup.26 1.5296 
(3) (CH.sub.2).sub.2 CH.sub.3 
n.sub.D.sup.25 1.5216 
(4) CH(CH.sub.3).sub.2 n.sub.D.sup.26 1.5194 
(5) (CH.sub.2).sub.3 CH.sub.3 
n.sub.D.sup.25 1.5195 
(6) 
##STR5## n.sub.D.sup.29 1.5124 
(7) CH.sub.2 CHCH.sub.2 n.sub.D.sup.28 1.5398 
(8) 
##STR6## n.sub.D.sup.25 1.5178 
(9) CH.sub.2 CCH n.sub.D.sup.25 1.5545 
(10) C(CH.sub.3).sub.3 n.sub.D.sup.26 1.5283 
(11) 
##STR7## n.sub.D.sup.28 1.5302 
(12) 
##STR8## n.sub.D.sup.22 1.5491 
(13) 
##STR9## n.sub.D.sup.29 1.5255 
(14) 
##STR10## n.sub.D.sup.29 1.5001 
(15) 
##STR11## n.sub.D.sup.25 1.5472 
(16) 
##STR12## m.p. 59.degree. C. 
(17) 
##STR13## n.sub.D.sup.25 1.5396 
(18) 
##STR14## n.sub.D.sup.18 1.5276 
(19) 
##STR15## n.sub.D.sup.19 1.5565 
(20) 
##STR16## n.sub.D.sup.22 1.5530 
(21) 
##STR17## n.sub.D.sup.24 1.5667 
(22) 
##STR18## m.p. 78-79.degree. C. 
(23) 
##STR19## n.sub.D.sup.21 1.5495 
(24) 
##STR20## n.sub.D.sup.22 1.5231 
(25) 
##STR21## n.sub.D.sup.25 1.5190 
(26) 
##STR22## n.sub.D.sup.23 1.5487 
(27) 
##STR23## n.sub.D.sup.22 1.5572 
(28) 
##STR24## n.sub.D.sup.24 1.5785 
______________________________________ 
When the present compounds are used as an active ingredient for an 
insecticidal and/or acaricidal composition, they may be used as such 
without adding any other ingredients. Generally, however, they are 
formulated into emulsifiable concentrates, wettable powders, dusts, 
granules, oil sprays, aerosols, heating fumigants (e.g. mosquito coils, 
electric mosquito mats, porous ceramic plates), foggings, non-heating 
fumigants, poisonous baits, etc. by mixing with solid carriers, liquid 
carriers, gaseous carriers, surface active agents, other auxiliaries for 
formulation, baits, etc., or impregnating into bases such as mosquito coil 
carriers, mats, etc. 
As described above, the insecticidal composition of the present invention 
is particularly suitable for the control of cockroaches so that, in using 
it for such purpose, its insecticidal effect can be developed more 
efficiently by using it in the form of a fumigant. The fumigant means one 
of the pesticide formulations which controls pests or fungi by dispersing 
the active ingredients into atmosphere in some way. 
As the form of such fumigant, there may be given, for example, types 
suitable for non-heating (e.g. mothprofer strip, insecticidal strip, 
mothball), burning (e.g. "jet" type formulations, "rod" type formulations, 
mosquito coil), exothermic reaction (e.g. types generating heat by water 
addition or air oxidation), electric heating (e.g. mat) and the like. 
As the mothprofer strip or insecticidal strip, there may be given, for 
example, strips produced by impregnating the paper, pulp, synthetic resin, 
etc. with an active ingredient. 
As the mothball, there may be given, for example, balls produced by 
hardening an active ingredient as such. 
As a main base for the "jet" type formulations, there are given, for 
example, mixtures of a nitrate or nitrite and a thermal 
decomposition-stimulating agent (e.g. salts of an alkaline earth metal or 
alkali metal), mixtures of a guanidine salt and a thermal 
decomposition-stimulating agent (e.g. bichromates, chromates), and the 
like. 
As a main base for the "rod" type formulations, there are given, for 
example, mixtures of a burning agent (e.g. ethyl cellulose, 
nitrocellulose), a flame-extinguishing agent (e.g. melamine, flour), a 
filler (e.g. diatomaceous earth) and a vehicle and the like. This mixture 
is kneaded and then formed into a rod. 
As a main base for mosquito coil, there are given, for example, mixture of 
a burning agent (e.g. wood powder, pyrethrum marc) and a setting agent 
(e.g. Tabu powder). This mixture is kneaded and then formed into a 
mosquito coil. 
As a main base for the type which generates heat by air oxidation, there 
are given, for example, mixtures of a heat-generating agent (e.g. 
sulfides, polysulfides or hydrosulfides of an alkali metal, their hydrated 
salts), a catalytic substance (e.g. carbon black, activated carbon, 
charcoal, coke, asphalt) and a filler (e.g. natural fibers, synthetic 
fibers, synthetic resin foams), and the like. 
As a main base for the type which generates heat by water addition, there 
are given, for example, mixtures of an organic foaming agent (e.g. 
azodicarbonamide, benzenesulfonyl hydrazide) and a heat-generating agent 
(e.g. calcium oxide), and the like. 
As the mat, there may be given, for example, mats produced by impregnating 
the porous plate of asbestos, pulp, ceramics, etc. with an active 
ingredient dissolved in an organic solvent such as acetone. 
These compositions contain 0.001 to 95% by weight of the present compound 
as an active ingredient. 
The solid carrier includes for example fine powders or granules of kaolin 
clay, attapulgite clay, bentonite, terra abla, pyrophyllite, talc, 
diatomaceous earth, calcite, corn stalk powder, walnut shell powder, urea, 
ammonium sulfate, synthetic hydrated silicon dioxide and the like. The 
liquid carrier includes for example aliphatic hydrocarbons (e.g. 
kerosene), aromatic hydrocarbons (e.g. benzene, toluene, xylene, 
methylnaphthalene), halogenated hydrocarbons (e.g. dichloroethane, 
trichloroethylene, carbon tetrachloride), alcohols (e.g. methanol, 
ethanol, isopropanol, ethylene glycol, cellosolve), ketones (e.g. acetone, 
methyl ethyl ketone, cyclohexanone, isophorone), ethers (e.g. diethyl 
ether, dioxane, tetrahydrofuran), esters (e.g. ethyl acetate), nitriles 
(e.g. acetonitrile, isobutyronitrile), acid amides (e.g. 
dimethylformamide, dimethylacetamide), dimethyl sulfoxide, vegetable oils 
(e.g. soybean oil, cotton seed oil) and the like. The gaseous carrier 
includes for example freon gas, LPG (liquefied petroleum gas), dimethyl 
ether and the like. The surface active agent used for emulsification, 
dispersion, wetting, etc. includes for example anionic surface active 
agents such as the salt of alkyl sulfates, alkyl(aryl)sulfonates, dialkyl 
sulfosuccinates, the salt of polyoxyethylene alkylaryl ether phosphoric 
acid ester, naphthalenesulfonic acid/formalin condensates, etc., and 
nonionic surface active agents such as polyoxyethylene alkyl ether, 
polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid 
esters, polyoxyethylene sorbitan fatty acid esters, etc. The auxiliary for 
formulation such as fixing agents, dispersing agents, etc. includes for 
example lignosulfonates, alginates, polyvinyl alcohol, gum arabic, 
molasses, casein, gelatin, CMC (carboxymethyl cellulose), pine oil, agar, 
etc. The stabilizer includes for example alkyl phosphates [e.g. PAP 
(isopropyl acid phosphate), TCP (tricresyl phosphate)], vegetable oils, 
epoxidized oils, the foregoing surface active agents, antioxidants (e.g. 
BHT, BHA), fatty acid salts (e.g. sodium oleate, calcium stearate), fatty 
acid esters (e.g. methyl oleate, methyl stearate) and the like. 
Formulation examples will be shown. The present compounds are shown by 
Compound No. described in Table 1. Parts in the examples are by weight. 
FORMULATION EXAMPLE 1 
0.2 Part of each of the present compounds (1) and (11), 2 parts of xylene 
and 97.8 parts of kerosene are mixed to obtain the oil spray of each 
compound. 
FORMULATION EXAMPLE 2 
Ten parts of each of the present compounds (1) to (28), 14 parts of 
polyoxyethylene styrylphenyl ether, 6 parts of calcium 
dodecylbenzenesulfonate and 70 parts of xylene are well mixed to obtain 
the emulsifiable concentrate of each compound. 
FORMULATION EXAMPLE 3 
Twenty parts of each of the present compounds (3) and (12), 10 parts of 
fenitrothion, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl 
sulfate and 65 parts of synthetic hydrated silicon dioxide are well 
pulverized and mixed together to obtain the wettable powder of each 
compound. 
FORMULATION EXAMPLE 4 
One part of each of the present compounds (4) and (13), 2 parts of 
Carbaryl, 87 parts of kaolin clay and 10 parts of talc are well pulverized 
and mixed together to obtain the dust of each compound. 
FORMULATION EXAMLE 5 
Five parts of each of the present compounds (5) and (15), 1 part of 
synthetic hydrated silicon dioxide, 2 parts of calcium lignosulfonate, 30 
parts of bentonite and 62 parts of kaolin clay are well pulverized and 
mixed together, well kneaded with water, granulated and then dried to 
obtain the granule of each compound. 
FORMULATION EXAMPLE 6 
0.05 Parts of each of the present compounds (6) and (16), 0.2 part of 
tetramethrin, 0.05 part of resmethrin, 7 parts of xylene and 32.7 parts of 
deodorized kerosene are well mixed into a solution. The solution is filled 
in an aerosol container, and after attaching a valve portion to the 
container, 60 parts of a propellant (liquefied petroleum gas) is charged 
therein through the valve under pressure to obtain the aerosol of each 
compound. 
FORMULATION EXAMPLE 7 
0.3 Gram of each of the present compounds (7) and (17) and 0.3 g of the 
d-trans-chrysanthemate of allethrin are dissolved in 20 ml of methanol. 
This solution and 99.4 g of a mosquito coil carrier, which is a 3:5:1 
mixture of Tabu powder, Pyrethrum marc and wood powder, are uniformly 
mixed with stirring. After evaporating methanol, 150 ml of water is added 
to the residue, and the mixture is well kneaded, shaped and dried to 
obtain the mosquito coil of each compound. 
FORMULATION EXAMPLE 8 
One hundred mg of each of the present compounds (1) to (28) is dissolved in 
a proper amount of acetone, and a porous ceramic plate of 4.0 cm.times.4.0 
cm.times.1.2 cm (thick) is impregnated with this solution to obtain the 
heating fumigant of each compound. 
These compositions are used as such or as aqueous dilute solutions. Also, 
they may be used in mixture with other insecticides, acaricides, 
namatocides, fungicides, herbicides, plant growth regulators, fertilizers, 
soil improvers and the like. 
When the present compounds are used in the form of emulsifiable concentrate 
or wettable powder as an insecticidal and/or acaricidal composition, their 
application concentration is 10 to 10000 ppm. When they are used in the 
form of dust, granule, oil spray or aerosol, they are applied as such 
without dilution. 
Test examples will be shown. Compounds used as a control are shown by 
Compound symbol in Table 2. 
TABLE 2 
______________________________________ 
Com- 
pound Structural 
symbol formula Name 
______________________________________ 
(A) 
##STR25## Compound described in B. P. No. 1,316,665 and 
U.S. Pat. No. 3,674,874. 
(B) 
##STR26## Compound described in U.S Pat. No. 3,674,874. 
(C) 
##STR27## Propoxur 
(D) 
##STR28## Malathion 
______________________________________ 
TEST EXAMPLE 1 
On the bottom of a polyethylene cup of 5.5 cm in diameter was placed a 
piece of filter paper of the same size as the bottom. 0.7 Milliliter of 
the 200-fold aqueous dilute solution (corresponding to 500 ppm of active 
ingredient) of emulsifiable concentrates, prepared from the present 
compounds according to Formulation example 2, was dropped down to the 
filter paper, and 30 mg of sucrose was uniformly placed on the filter 
paper as bait. Thereafter, 10 female adult houseflies (Musca domestica) 
were liberated in the cup which was then covered with a lid. After 24 
hours, the number of the dead and alive was examined to obtain a mortality 
(two replications). 
The result is shown in Table 3. 
TABLE 3 
______________________________________ 
Test compound Mortality (%) 
______________________________________ 
(1) 100 
(2) 100 
(3) 100 
(4) 100 
(5) 100 
(6) 100 
(7) 100 
(8) 100 
(9) 100 
(13) 100 
(15) 100 
(17) 100 
(19) 100 
(20) 100 
(21) 100 
(24) 100 
(25) 100 
No treatment 0 
______________________________________ 
TEST EXAMPLE 2 
The rice seedlings (about 12 cm in length) were dipped for 1 minute in the 
200-fold aqueous dilute solution (corresponding to 500 ppm of active 
ingredient) of emulsifiable concentrates, prepared from the present 
compounds and the control according to Formulation example 2. After 
air-drying, the seedlings were placed in a test tube, and 10 adult green 
rice leafhoppers, Nephotettix cincticeps, (resistant strain) were 
liberated therein. After one day, the number of the dead and alive was 
examined to obtain a mortality (two replications). 
The result is shown in Table 4. 
TABLE 4 
______________________________________ 
Test compound Mortality (%) 
______________________________________ 
(3) 100 
(5) 100 
(6) 100 
(A) 60 
(B) 20 
(D) 50 
No treatment 5 
______________________________________ 
TEST EXAMPLE 3 
On the bottom of a polyethylene cup of 5.5 cm in diameter was placed a 
piece of filter paper of the same size as the bottom. 0.7 Milliliter of an 
aqueous dilute solution of prescribed concentrations, prepared from the 
emulsifiable concentrates of the present compounds and the control 
formulated according to Formulation example 2, was dropped down to the 
filter paper, and 30 mg of sucrose was placed on the filter paper as bait. 
Thereafter, 10 male adults of German cockroaches (Blattella germanica) 
were liberated in the cup which was then covered with a lid. After 72 
hours, the number of the dead and alive was examined to obtain LC.sub.50 
value (50% lethal concentration) (two replications). 
The result is shown in Table 5. 
TABLE 5 
______________________________________ 
Test compound LC.sub.50 (ppm) 
______________________________________ 
(1) 2.7 
(2) 3.3 
(3) 7.4 
(4) 2.7 
(5) 6.1 
(7) 8.7 
(9) 8.7 
(11) 21 
(12) 23 
(13) 14 
(15) 17 
(16) 17 
(17) 21 
(18) 23 
(19) 8.7 
(20) 21 
(21) 19 
(22) 22 
(24) 11 
(25) 8.7 
(28) 9.0 
(A) 30 
(C) .apprxeq.150 
______________________________________ 
TEST EXAMPLE 4 
The present compounds and the control were each diluted with acetone to 
prescribed concentrations and topically applied to the ventral thorax of 
the male adults of German cockroaches (Blattella germanica) at a rate of 1 
.mu.l/adult. After application, the adults were bred on bait and water in 
a polyethylene cup. After two days, the number of the dead and alive was 
examined to obtain LD.sub.50 value (50% lethal dosage) (10 adults per 
group; two replications). 
The result is shown in Table 6. 
TABLE 6 
______________________________________ 
Test compound LD.sub.50 (.mu.g/.male.) 
______________________________________ 
(1) 0.18 
(2) 0.25 
(3) 0.33 
(4) 0.17 
(5) 0.25 
(7) 0.21 
(9) 0.16 
(12) 0.37 
(13) 0.22 
(19) 0.27 
(21) 0.18 
(25) 0.32 
(A) &gt;1 
______________________________________ 
TEST EXAMPLE 5 
Four polyethylene cups (inside diameter, 10 cm; height, 8 cm) coated with 
butter at the inside surface were set at the four corners, respectively, 
of the bottom of a (70 cm).sup.3 glass chamber (0.34 m.sup.3). Ten male 
adults per group of German cockroaches (Blattella germanica) were 
liberated in each of two polyethylene cups, and 10 female adults per group 
of the insects were liberated in each of the remaining two. An electric 
heater was set at the center of the bottom of the glass chamber, and each 
of the porous ceramic plates impregnating the present compounds and the 
control according to Formulation example 8 (13.7 mg/mat; 40 mg/m.sup.3), 
was placed thereon. The mat was heated to about 200.degree. C. by applying 
current for 20 minutes. Eighty minutes after current application was 
started, the cups containing the test insects were taken out of the 
chamber, and the test insects were bred on water and bait. After two days, 
the number of the dead and alive was examined to obtain a mortality. 
The result is shown in Table 7. 
TABLE 7 
______________________________________ 
Test compound Mortality (%) 
______________________________________ 
(1) 100 
(2) 100 
(3) 100 
(4) 100 
(6) 100 
(7) 100 
(8) 100 
(9) 100 
(10) 100 
(11) 100 
(12) 100 
(13) 100 
(15) 100 
(16) 100 
(17) 100 
(18) 100 
(21) 100 
(22) 100 
(23) 97.5 
(25) 100 
(26) 100 
(27) 100 
(28) 97.5 
(A) 47.5 
(C) 0 
______________________________________ 
TEST EXAMPLE 6 
At the bottom of a (183 cm).sup.3 Peet Grady's chamber (6.1 m.sup.3) were 
placed three polyethylene cups (inside diameter, 10 cm; height, 8 cm) 
coated with butter at the inside surface, and 20 adult German cockroaches 
(10 males and 10 females) (Blattella germanica) were liberated in each 
cup. An electric heater was set at the center of the bottom of the 
chamber, and each of the porous ceramic plates impregnating the present 
compounds and the control according to Formulation example 8 (61 mg/mat; 
10 mg/m.sup.3), was placed thereon. The plate was heated to about 
200.degree. C. by applying current for 70 minutes. The number of 
knocked-down insects with the lapse of time was examined to obtain 
KT.sub.50 value (50% knocked-down time). Eighty minutes after current 
application was started, the cups containing the test insects were taken 
out of the chamber, and the test insects were bred on water and bait. 
After three days, the number of the dead and alive was examined to obtain 
a mortality. 
The result is shown in Table 8. 
TABLE 8 
______________________________________ 
Test KT.sub.50 
Mortality 
compound (minute) (%) 
______________________________________ 
(12) 57' 87.5 
(21) 72' 95 
(A) &gt;80' 0 
(C) &gt;80' 0 
______________________________________ 
TEST EXAMPLE 7 
The female adults of carmine spider mites (Tetranychus cinnabarinus) were 
made parasitic on the leaves of potted kidney bean (at the primordial leaf 
stage) which had elapsed 7 days after sowing at a rate of 10 adults/leaf, 
and placed in a constant-temperature room kept at 25.degree. C. After 6 
days, the emulsifiable concentrate of the present compounds formulated 
according to Formulation example 2 was diluted with water so that the 
concentration of active ingredient was 500 ppm, and 10 ml of the aqueous 
dilute solution was sprayed onto the plant on a turn table by a spray gun. 
At the same time, the soil in the pot was drenched with 2 ml of the same 
solution. After 8 days, the degree of damage of the plant by the mites was 
examined. 
The degree of damage is expressed in the following three grades: 
-: Any damage is not observed. 
+: Slight damage is observed. 
++: The same damage as in the untreated plot is observed. 
The result is shown in Table 9. 
TABLE 9 
______________________________________ 
Test compound Degree of damage 
______________________________________ 
(2) - .about. + 
(7) - .about. + 
(9) - 
(13) - 
(14) - 
(24) - .about. + 
No treatment ++ 
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