Note: Descriptions are shown in the official language in which they were submitted.
CA 02040370 2000-03-31
INSECTICIDAL COMPOSITIONS
1 The present invention relates to an
insecticidal composition.
2,4-Dioxo-1-(2-propynyl)imidazolidin-3-
ylmethyl chrysanthemate having the formula (hereinafter
Compound A),
O O
CH = CCH2~~ CH20C CH=C(CH3)2
l~\p CH3 CH3
is a compound disclosed in USP 4,176,189, and is known
to be usable as an active ingredient for insecticides.
However, the compound does not exhibit a satisfactorily
high insecticidal activity when used alone.
1.0 The present inventors have extensively studied
to strengthen the insecticidal activity of Compound A,
and as a result have found that when (b) at least one
carboxylic acid ester selected from the group consisting
of monocarboxylic acid esters having 16 to 19 carbon
1.5 atoms and dicarboxylic acid esters having 16 to 19
carbon atoms is added to (a) Compound A so that the
weight ratio of (a) to (b) is from 3:1 to 1:100, the
insecticidal activity of Compound A is remarkably
strengthened. The present inventors have thus attained
~0 to the present invention.
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2~4Q3~0
1 According to the present invention, there is
provided an insecticidal composition comprising:
(a) 2,4-dioxo-1-(2-propynyl)imidazolidin-3-
ylmethyl chrysanthemate (Compound A),
(b) at least one member selected from the group
consisting of monocarboxylic acid esters having 16 to 19
carbon atoms and dicarboxylic acid esters having 16 to
19 carbon atoms, the weight ratio of (a) to (b) being
from 3:1 to 1:100, and optionally
l0 (c) at least one inert carrier.
Compound A includes various optical and
geometrical isomers. Of the isomers, an isomer
exhibiting an insecticidal activity and the mixtures
thereof can be incorporated in the insecticidal
composition of the present invention. The content of
Compound A in the composition of the present invention
is usually 0.001% to 75% by weight.
Specific examples of the monocarboxylic acid
esters having 16 to 19 carbon atoms and the dicarboxylic ,
acid esters having 16 to 19 carbon atoms are dibutyl
phthalate, isopropyl palmitate, isopropyl myristate,
hexyl laurate, etc. These compounds may also be used in
admixture thereof. One or more compounds selected out
of these compounds are usually blended in the
composition of the present invention in an amount of
0.0003% to 75% by weight.
Into the composition of the present invention
may be incorporated one or more of other insecticides,
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2403:~
1 synergists, perfumes, fungicides, solvents, propellants,
solid carriers, etc.
Specific examples of the other insecticides
are:
(RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl
(1RS)-cis,trans-chrysanthemate [allethrin];
3.4,5,6-tetrahydrophthalimidomethyl (1RS)-
cis,trans-chrysanthemate [tetramethrin];
(S)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-
enyl (1R)-cis,trans-chrysanthemate [prallethrin];
3-phenoxybenzyl (1RS)-cis,trans-chrysanthemate
[phenothrin];
5-benzyl-3-furylmethyl (1RS)-cis,trans-
chrysanthemate [resmethrin];
(RS)-a-cyano-3-phenoxybenzyl (1R)-cis,trans-
chrysanthemate [cyphenothrin];
3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-
dichlorovinyl)-2,2-dimethylcyclopropanecaboxylate
[permethrin];
(RS)-a-cyano-3-phenoxybenzyl (1RS)-cis,trans-
3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-
carboxylate [cypermethrin];
(S)-a-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-
dibromovinyl)-2,2-dimethylcyclopropanecarboxylate
[deltamethrin];
(RS)-a-cyano-4-fluoro-3-phenoxybenzyl (1RS)-
ci~,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclo-
propanecarboxylate [cyfluthrin];
-
2~~~3~~
1 5-(2-propynyl)furufuryl (1RS)-cis,trans-
chrysanthemate [furamethrin];
2-(4-ethoxyphenyl)-2-methylpropyl 3-
phenoxybenzyl ether [ethofenprox];
2,2-dichlorovinyl dimethyl phosphate
[dichlorvos];
O,0-dimethyl O-(3-methyl-4-nitrophenyl)-
phosphorothioate [fenitrothion];
2-(1-methyethoxy)phenyl methylcarbamate
[propoxur];
4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl
ether [pyriproxyfen];
isopropyl (2E,4E)-11--methoxy-3,7,11-trimethyl-
2,4-dodecadienoate [methoprene];
ethyl (2E,4E)-3,7,11-trimethyldodeca-2,4-
dienoate [hydroprene];
1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea
[diflubenzuron]; and
N-cyclopropyl-1,3,5-triazine-2,4,6-triamine
[cyromazine].
Specific examples of the synergists are a-[2-
(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-
propyltoluene (piperonyl butoxide), N-(2-ethylhexyl)-
bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide (MGK-264),
octachlorodipropyl ether (S-421), etc.
Specific examples of the solvents are
isopropyl alcohol, kerosene, dodecylbenzene, etc.
- 4 -
:o~o~~o
1 Specific examples of the propellants are
propane/butane, dimethyl ether, FreonTM gas
( f:luorocarbons ) , etc .
The composition of the present invention is
prepared, for example, by mixing a prescribed amount of
Compound A and a prescribed amount of at least one
carboxylic acid ester described above, and if necessary
other insecticides, synergists, perfumes, fungicides,
solvents, propellants, solid carriers, etc. at room
20 temperature or under heating.
Insects and acarina against which the
composition of the present invention thus prepared is
effective are listed below:
Lepidoptera
casemaking clothes moth (Tinea nellionella),
webbing clothes moth (Tineola bisselliella),
etc.
Diptera
Culex spp. such as common mosquito (Culex
pipiens pallens) and Culex tritaeniorhynchus;
Aedes spp. such as Aedes aegypti; and Aedes
albopictus; Anor~heles spp. such as Anopheles
sinensis midges (Chironomidae);
Muscidae such as housefly (Musca domestica)
and false stablefly (Muscina stabulans);
Calliphoridae; Sarcophagidae; little housefly
(Fannia canicularis);
- 5 -
20403'0
1 Anthomyiidae such as seedcorn maggot (Delia
platura) and onion maggot (Delia antiaua);
fruit flies (Tephritidae); Drosophilidae; moth
flies (Psychodidae); black flies (Simuliidae);
Tabanidae; stable flies (Stomoxyidae) etc.
Dictyoptera
German cockroach (Blattella germanica),
smokybrown cockroach (Periplaneta ful'_q_inosa),
American cockroach (Periplaneta americana),
brown cockroach (Periplaneta brunnea),
oriental cockroach (Blatta orientalis), etc.
Hymenoptera
ants (Formicidae), hornets (Vespidae);
Bethylidae, sawflies (Tenthredinidae) such as
cabbage sawfly (Athalia rosae ruficornis),
etc.
Isoptera
Reticulitermes speratus, Coptotermes
formosanus etc.
Ixodidae
Boophilus microplus, etc.
House dust mites
Acaridae such as Tyrophagus putrescentiae,
Pyroalyphidae such as Dermatopha9oides
farinae, Cheyletidae such as Chelacaropsis
moorei, Macronyssidae such as Ornithonyssus
bacoti, etc.
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1 The composition of the present invention can
b~e used as it is for killing the insect pests; however,
it is usually used formulated into the form of
preparation such as aerosols, oil sprays, etc. In the
latter case, the content ef Compound A in the aerosols
or in the oil sprays is preferably 0.001 to 5~ by
weight.
The present invention is illustrated in more
detail with reference to the following Examples,
Comparative Examples and Test Example;
however, the present invention should not be interpreted
as being limited thereto.
In Examples, Comparative Examples and Test
Example, parts are by weight.
Example 1
50.0 Parts of Compound A (acid moiety: d-
trans configuration) and 50.0 parts of isopropyl
myristate were mixed under heating (about 40 to 50°C) to
obtain a liquid insecticidal composition.
Table 1 lists the insecticidal compositions
obtained in the same manner as above.
2040~'~0
0 0 0 0 0 0 0 0 0
0 0
~
W U
ro
U
r-I
1J
~ro
H O O O O O O O O O O
O
ro u1
W v
1~
N
v
0 0 0 0
0
0 0 0 0 0 0 m
~ O
'
.
~ rl
b
r-I
v ~
rorov
0 0 0 0 0 0 0 0 0 0
0
N
",e'~ ~
, r~i
.,
x
a p v
ro
o 0 0 0 0 0 0 0 0 0
0
rox sr
U 'J'
Clv
N
O
rl
rl .-I '--I
I
~ ~~~ O O O O O O O O O A
.aJ O
~'
H
ro O W W '
H U
~-~I
I
I ~r
N v p1 O O O O O O O O O
a.,~ O
.~.7
N O ov o w,M
>a
ro
H a
9~f
.i.~
I
ro
~'dN
H
rl 0 0 0 0 0 0 0 0 0
0
~ ri tf1t~tf1lf1tl1O Lf1 tf1
LT l U'1
O
r1 r
~
rob
~
U
r-1N M d~tff1GC~ rl N
M
d'
v
U rl
v
ro
s~
W ~W
O
U
~0~03~0
1 Example 8
0.1 Part of Compound A, 0.1 part of isopropyl
myristate and 0.3 part of cyphenothrin were dissolved in
a mixture of 20.0 parts of dodecylbenzene and 39.5 parts
of kerosene. The resulting mixture was charged in a
container. A nozzle was provided to the container.
40.0 Parts of a propellant mixture of propane and butane
was compressed through the nozzle into the insecticidal
composition to obtain an aerosol.
Example 9
1.0 Part of Compound A and 1.0 part of
isopropyl myristate were disso'_ved in a mixture ef 20.0
parts of isopropyl alcohol and 28.0 parts of kerosene.
The resulting mixture was charged in a container. A
nozzle was provided to the container. 50.0 Parts of a
propellant mixture of propane, butane and dimethyl ether
was compressed through the nozzle into the insecticidal
composition to obtain an aerosol.
Example 10
1.0 Parts of Compound A and 31.0 parts of
isopropyl myristate were dissolved in 18.0 parts of
kerosene. The resulting mixture was charged in a
container. A nozzle was provided to the container.
50.0 Parts of a propellant mixture of propane, butane
and dimethyl ether was compressed through the nozzle
into the insecticidal composition to obtain an aerosol.
_ g _
zo~o3~0
1 Example 11
1.0 Part of Compound A and 1.0 part of dibutyl
phthalate were dissolved in a mixture of 2.5 parts of
isopropyl alcohol and 45.5 parts of dodecylbenzene. The
resulting mixture was changed in a container. A nozzle
was provided to the container. 50.0 Parts of a
propellant mixture of propane, butane and dimethyl ether
was compressed through the nozzle into the insecticidal
composition to obtain an aerosol.
Test Example
Each of the insecticidal compositions obtained
in Examples 1 to 7 and Comparative Examples 1 to 4 was
diluted with acetone to obtain a solution containing
0.189 g/~ of Compound A. 0.3 Milliliter of the solution
was coated onto a petri dish of 8.5 cm in diameter so
that Compound A was attached to the petri dish in an
amount of 0.0567 mg. That isr Compound A was attached
to the petri dish in a ratio of 10 mg/m2. After the
petri dish had been dried by evaporation of acetone, 10
German cockroaches (Blattella aermanica) were released
therein. The knock-down effect, KT50 (a time required
for knocking down 50~ of the cockroaches) was
determined. Table 2 shows the results.
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2U403'~~
Table 2
KZ50 (min) to
German cockroach
1 0.8
2 0.9
3 1.0
Example
4 0.9
5 7..1
6 0.9
'7 1.2
1 3.0
Comparative2 2.8
Example 3 4.1
4 3.3
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