U.S. patent application number 10/504158 was filed with the patent office on 2005-09-29 for composition for controlling house insect pest and method for controlling house insect pest.
This patent application is currently assigned to Ishihara Sangyo Kaisha, Ltd. Invention is credited to Imai, Osamu, Morita, Masayuki.
Application Number | 20050215597 10/504158 |
Document ID | / |
Family ID | 27759678 |
Filed Date | 2005-09-29 |
United States Patent
Application |
20050215597 |
Kind Code |
A1 |
Morita, Masayuki ; et
al. |
September 29, 2005 |
Composition for controlling house insect pest and method for
controlling house insect pest
Abstract
The present invention provides a composition for controlling a
house insect pest, such as termites, ants or cockroaches, which
comprises, as active ingredients, at least two compounds selected
from the group consisting of (a) a certain pyridine compound, (b) a
benzoylurea compound, (c) a pyrethroid compound and (d) a certain
hydrazone compound; and a composition for controlling a house
insect pest, which comprises, as an active ingredient, a certain
hydrazone compound.
Inventors: |
Morita, Masayuki; (Shiga,
JP) ; Imai, Osamu; (Shiga, JP) |
Correspondence
Address: |
OBLON, SPIVAK, MCCLELLAND, MAIER & NEUSTADT, P.C.
1940 DUKE STREET
ALEXANDRIA
VA
22314
US
|
Assignee: |
Ishihara Sangyo Kaisha, Ltd
3-15, Edobori 1-chome Nishi-ku, Osaka-shi
Osaka
JP
550-0002
|
Family ID: |
27759678 |
Appl. No.: |
10/504158 |
Filed: |
May 16, 2005 |
PCT Filed: |
February 18, 2003 |
PCT NO: |
PCT/JP03/01711 |
Current U.S.
Class: |
514/341 ;
514/355 |
Current CPC
Class: |
A01N 2300/00 20130101;
A01N 2300/00 20130101; A01N 53/00 20130101; A01N 35/10 20130101;
A01N 37/38 20130101; A01N 2300/00 20130101; A01N 37/38 20130101;
A01N 53/00 20130101; A01N 35/10 20130101; A01N 47/34 20130101; A01N
2300/00 20130101; A01N 35/10 20130101; A01N 37/38 20130101; A01N
47/34 20130101; A01N 35/10 20130101; A01N 43/40 20130101; A01N 3/00
20130101; A01N 35/10 20130101; A01N 35/10 20130101; A01N 47/34
20130101; A01N 53/00 20130101; A01N 43/40 20130101; A01N 53/00
20130101; A01N 43/40 20130101; A01N 53/00 20130101; A01N 47/34
20130101 |
Class at
Publication: |
514/341 ;
514/355 |
International
Class: |
A01N 043/40 |
Foreign Application Data
Date |
Code |
Application Number |
Feb 22, 2002 |
JP |
2002-045837 |
Aug 2, 2002 |
JP |
2002-226478 |
Claims
1. A composition for controlling a house insect pest, which
comprises, as active ingredients, at least two compounds selected
from the group consisting of (a) a pyridine compound of the formula
(I) or it salt: 14wherein Y is a haloalkyl group, m is 0 or 1, and
Q is 15or a substituted or unsubstituted heterocyclic group,
(wherein X is an oxygen atom or a sulfur atom, R.sup.1 and R.sup.2
are respectively independently a hydrogen atom, a substituted or
unsubstituted alkyl group, a substituted or unsubstituted alkenyl
group, a substituted or unsubstituted alkynyl group, a substituted
or unsubstituted cycloalkyl group, a --C(W.sup.1)R.sup.3 group, a
--OR.sup.4 group, a --S(O).sub.nR.sup.5 group, a --NHR.sup.6 group,
16a --C(R.sup.8).dbd.NO--R.sup.9 group or a substituted or
unsubstituted aryl group, or R.sup.1 and R.sup.2 may form a
.dbd.C(R.sup.10)R.sup.11 group or may form a C.sub.4-C.sub.5
5-membered or 6-membered heterocyclic group which may contain a
nitrogen atom or an oxygen atom, together with an adjacent nitrogen
atom, R.sup.3 is a substituted or unsubstituted alkyl group, a
substituted or unsubstituted alkenyl group, a substituted or
unsubstituted alkynyl group, a substituted or unsubstituted
cycloalkyl group, a substituted or unsubstituted aryl group, an
alkoxy group, an alkylthio group or a mono- or dialkylamino group,
R.sup.4 is a hydrogen atom, a substituted or unsubstituted alkyl
group, a substituted or unsubstituted alkenyl group, a substituted
or unsubstituted alkynyl group, a substituted or unsubstituted
cycloalkyl group, a substituted or unsubstituted aryl group, a
substituted or unsubstituted heterocyclic group or a --COR.sup.3
group, R.sup.5 is an alkyl group or a dialkylamino group, R.sup.6
is an alkyl group or an aryl group, Z is N or a --C--R.sup.7 group,
R.sup.7 is a hydrogen atom, a halogen atom, a substituted or
unsubstituted alkyl group, an alkoxy group, an alkylthio group or a
nitro group, R.sup.8 and R.sup.9 are respectively independently a
hydrogen atom, a substituted or unsubstituted alkyl group, a
substituted or unsubstituted alkenyl group, a substituted or
unsubstituted alkynyl group, a substituted or unsubstituted aryl
group or a substituted or unsubstituted heterocyclic group,
R.sup.10 and R.sup.11 are respectively independently a hydrogen
atom, a substituted or unsubstituted alkyl group, a substituted or
unsubstituted alkenyl group, a substituted or unsubstituted
heterocyclic group, a --N--(R.sup.12)R.sup.13 group, a substituted
or unsubstituted alkoxy group, a substituted or unsubstituted
alkylthio group, R.sup.12 and R.sup.13 are respectively
independently a hydrogen atom, a substituted or unsubstituted alkyl
group, a substituted or unsubstituted alkenyl group, a substituted
or unsubstituted alkynyl group, a substituted or unsubstituted aryl
group or a substituted or unsubstituted heterocyclic group, W.sup.1
is an oxygen atom or a sulfur atom, and n is 1 or 2), (b) a
benzoylurea compound, (c) a pyrethroid compound and (d) a hydrazone
compound of the formula (II) or its salt: 17wherein each of
R.sup.1', R.sup.2' and R.sup.4', which are independent of one
another, is a hydrogen atom, a halogen atom, an alkyl group which
may be substituted by halogen, or an alkoxy group which may be
substituted by halogen, R.sup.3' is a halogen atom, an alkyl group
which may be substituted by halogen, or an alkoxy group which may
be substituted by halogen, R.sup.5' is a hydrogen atom, or an alkyl
group, R.sup.6' is X.sup.7' CO-- (wherein X.sup.7' is a hydrogen
atom, or an alkyl group), or X.sup.8' OCO-- (wherein X.sup.8' is an
alkyl group), or R.sup.5' and R.sup.6' together form
.dbd.CR.sup.7'R.sup.8' (wherein R.sup.7' is a hydrogen atom, or an
alkyl group, and R.sup.8' is an amino group which may be
substituted by alkyl, or an alkoxy group).
2. The composition according to claim 1, wherein Q in the formula
(I) is 18(wherein X is an oxygen atom or a sulfur atom, R.sup.1 and
R.sup.2 are respectively independently a hydrogen atom, a
substituted or unsubstituted alkyl group, a substituted or
unsubstituted alkenyl group, a substituted or unsubstituted alkynyl
group, a substituted or unsubstituted cycloalkyl group, a
--C(W.sup.1)R.sup.3 group, a --S(O)nR.sup.5 or a --NHR.sup.6 group,
or R.sup.1 and R.sup.2 may form a .dbd.C(R.sup.10)R.sup.11 group or
a C.sub.4-C.sub.5 5-membered or 6-membered heterocyclic group which
may contain a nitrogen atom or an oxygen atom, together with an
adjacent nitrogen atom, R.sup.3 is a substituted or unsubstituted
alkyl group, a substituted or unsubstituted alkenyl group, a
substituted or unsubstituted alkynyl group, a substituted or
unsubstituted cycloalkyl group, a substituted or unsubstituted aryl
group, an alkoxy group, an alkylthio group or a mono- or
dialkylamino group, R.sup.5 is an alkyl group or a dialkylamino
group, R.sup.6 is an alkyl group or an aryl group, R.sup.10 and
R.sup.11 are respectively independently an alkoxy group or an
alkylthio group, W.sup.1 is an oxygen atom or a sulfur atom, and n
is 1 or 2).
3. The composition according to claim 1, wherein (a) the pyridine
compound is N-cyanomethyl-4-trifluoromethyl-3-pyridinecarboxyamide
or its salt.
4. The composition according to claim 1, wherein (b) the
benzoylurea compound is at least one compound selected from the
group consisting of Diflubenzuron, Chlorfluazuron, Teflubenzuron,
Flufenoxuron, Triflumuron, Hexaflumuron, Lufenuron, Novaluron and
Noviflumuron.
5. The composition according to claim 4, wherein (b) the
benzoylurea compound is Chlorfluazuron and/or Hexaflumuron.
6. The composition according to claim 1, wherein (c) the pyrethroid
compound is Bifenthrin.
7. A composition for controlling a house insect pest, which
comprises, as an active ingredient, a hydrazone compound of the
formula (II) or its salt: 19wherein each of R.sup.1', R.sup.2' and
R.sup.4', which are independent of one another, is a hydrogen atom,
a halogen atom, an alkyl group which may be substituted by halogen,
or an alkoxy group which may be substituted by halogen, R.sup.3' is
a halogen atom, an alkyl group which may be substituted by halogen,
or an alkoxy group which may be substituted by halogen, R.sup.5' is
a hydrogen atom, or an alkyl group, R.sup.6' is X.sup.7' CO--
(wherein X.sup.7' is a hydrogen atom, or an alkyl group), or
X.sup.8' OCO-- (wherein R.sup.7' is an alkyl group), or R.sup.5'
and R.sup.6' together form .dbd.CR.sup.7'R.sup.8' (wherein R.sup.7'
is a hydrogen atom, or an alkyl group, and R.sup.8' is an amino
group which may be substituted by alkyl, or an alkoxy group).
8. The composition according to claim 7, wherein the hydrazone
compound is at least one compound selected from the group
consisting of
[4'-chloro-2-(4-trifluoromethylphenyl)acetophenone]N'-[1-(dimethylamino)e-
thylidene]hydrazone,
[4'-fluoro-2-(4-trifluoromethylphenyl)acetophenone]N'-
-[1-(dimethylamino)ethylidene]hydrazone, ethyl
3-[1-(4-chlorophenyl)-2-(4--
trifluoromethylphenyl)ethylidene]-carbazate,
[4'-chloro-2-(4-tert-butylphe-
nyl)acetophenone]N'-[1-(dimethylamino)ethylidene]hydrazone,
[4'-fluoro-2-(4-tert-butylphenyl)acetophenone]N'-[1-(dimethylamino)ethyli-
dene]hydrazone,
[4'-methyl-2-(4-tert-butylphenyl)acetophenone]N'-[1-(dimet-
hylamino)ethylidene]hydrazone and
[4'-chloro-2-(4-trifluoromethylphenyl)ac-
etophenone]N'-[1-aminoethylidene]hydrazone.
9. The composition according to claim 7, which is in the form of a
poison bait chemical.
10. The composition according to claim 9, wherein the base material
for the poison bait chemical is bait log or fresh pulp.
11. The composition according to claim 7, which is in the form of a
gel containing a water-absorptive polymer and having a
water-holding property.
12. The composition according to claim 7, which is in the form of a
dust containing cellulose and/or titanium oxide.
13. The composition according to claim 7, which is in the form of a
soil treating agent.
14. The composition according to claim 1 or 7, wherein the house
insect pest is at least one member selected from the group
consisting of a termite, an ant and a cockroach.
15. The composition according to claim 1 or 7, wherein the house
insect pest is a termite.
16. The composition according to claim 1 or 7, wherein the house
insect pest is an ant.
17. The composition according to claim 1 or 7, wherein the house
insect pest is a cockroach.
18. A method for controlling a house insect pest, which comprises
applying the composition as defined in claim 1 or 7 to its
habitat.
19. The controlling method according to claim 18, wherein the
composition is fed or contacted to the house insect pest.
20. The controlling method according to claim 19, wherein the
composition is applied to an ant trail or is directly coated to a
damaged portion, to control a termite or an ant.
21. The controlling method according to claim 19, wherein the
composition is set in a baiting system.
Description
TECHNICAL FIELD
[0001] The present invention relates to a composition for
controlling a house insect pest, which comprises, as active
ingredients, at least two compounds selected from the group
consisting of (a) a certain specific pyridine compound or its salt,
(b) a benzoylurea compound, (c) a pyrethroid compound and (d) a
certain specific hydrazone compound or its salt, particularly to a
composition for controlling termites, ants or cockroaches. Further,
it relates also to a composition for controlling a house insect
pest, which comprises, as an active ingredient, the above hydrazone
compound or its salt.
BACKGROUND ART
[0002] Pyridine compounds may, for example, be those described in
e.g. U.S. Pat. No. 5,360,806, WO98/57969 and WO 02/34050. Hydrazone
compounds may be those described in U.S. Pat. No. 5,288,727 and
Japanese patent 307192.
[0003] As conventional agents for controlling termites,
organophosphorus compounds such as chlorpyrifos, or pyrethroids
may, for example, be mentioned. Further, as agents for controlling
ants, hydramethylnon, lithium sulfonate, organophosphorus
compounds, carbamates, or pyrethroids, may, for example, be
mentioned. Further, as agents for controlling cockroaches,
pyrethroids or organophosphorus compounds, may, for example, be
mentioned. However, among them, there are some which are feared to
present toxicity against mammals or adverse effects to environment.
Under the circumstances, a new agent for controlling a house insect
pest is desired.
DISCLOSURE OF THE INVENTION
[0004] The present inventors have conducted an extensive research
for an agent for controlling a house insect pest. As a result, they
have found specifically that by combining at least two compounds
selected from the group consisting of (a) certain specific pyridine
compounds or salts thereof, (b) benzoylurea compounds, (c)
pyrethroid compounds and (d) certain specific hydrazone compounds
or salts thereof, as active ingredients, particularly excellent
effects for controlling house insect pests can be expressed, and
that certain hydrazone compounds or salts thereof have excellent
effects for controlling house insect pests. The present invention
has been accomplished on the basis of this discovery.
[0005] Namely, the present invention provides a composition for
controlling a house insect pest, which comprises, as active
ingredients, at least two compounds selected from the group
consisting of (a) a pyridine compound of the formula (I) or its
salt: 1
[0006] wherein Y is a haloalkyl group, m is 0 or 1, and Q is 2
[0007] or a substituted or unsubstituted heterocyclic group,
(wherein X is an oxygen atom or a sulfur atom, R.sup.1 and R.sup.2
are respectively independently a hydrogen atom, a substituted or
unsubstituted alkyl group, a substituted or unsubstituted alkenyl
group, a substituted or unsubstituted alkynyl group, a substituted
or unsubstituted cycloalkyl group, a --C(W.sup.1)R.sup.3 group, a
--OR.sup.4 group, a --S(O).sub.nR.sup.5 group, a --NHR.sup.6 group,
3
[0008] a --C(R.sup.8).dbd.NO--R.sup.9 group or a substituted or
unsubstituted aryl group, or R.sup.1 and R.sup.2 may form a
.dbd.C(R.sup.10)R.sup.11 group or may form a
C.sub.4-C.sub.55-membered or 6-membered heterocyclic group which
may contain a nitrogen atom or an oxygen atom, together with an
adjacent nitrogen atom, R.sup.3 is a substituted or unsubstituted
alkyl group, a substituted or unsubstituted alkenyl group, a
substituted or unsubstituted alkynyl group, a substituted or
unsubstituted cycloalkyl group, a substituted or unsubstituted aryl
group, an alkoxy group, an alkylthio group or a mono- or
dialkylamino group, R.sup.4 is a hydrogen atom, a substituted or
unsubstituted alkyl group, a substituted or unsubstituted alkenyl
group, a substituted or unsubstituted alkynyl group, a substituted
or or unsubstituted cycloalkyl group, a substituted or
unsubstituted aryl group, a substituted or unsubstituted
heterocyclic group or a --COR.sup.3 group, R.sup.5 is an alkyl
group or a dialkylamino group, R.sup.6 is an alkyl group or an aryl
group, Z is N or a --C--R.sup.7 group, R.sup.7 is a hydrogen atom,
a halogen atom, a substituted or unsubstituted alkyl group, an
alkoxy group, an alkylthio group or a nitro group, R.sup.8 and
R.sup.9 are respectively independently a hydrogen atom, a
substituted or unsubstituted alkyl group, a substituted or
unsubstituted alkenyl group, a substituted or unsubstituted alkynyl
group, a substituted or unsubstituted aryl group or a substituted
or unsubstituted heterocyclic group, R.sup.10 and R.sup.11 are
respectively independently a hydrogen atom, a substituted or
unsubstituted alkyl group, a substituted or unsubstituted alkenyl
group, a substituted or unsubstituted heterocyclic group, a
--N--(R.sup.12)R.sup.13 group, a substituted or unsubstituted
alkoxy group, a substituted or unsubstituted alkylthio group,
R.sup.12 and R.sup.13 are respectively independently a hydrogen
atom, a substituted or unsubstituted alkyl group, a substituted or
unsubstituted alkenyl group, a substituted or unsubstituted alkynyl
group, a substituted or unsubstituted aryl group or a substituted
or unsubstituted heterocyclic group, W.sup.1 is an oxygen atom or a
sulfur atom, and n is 1 or 2); (b) a benzoylurea compound; (c) a
pyrethroid compound and (d) a hydrazone compound of the formula
(II) or its salt: 4
[0009] wherein each of R.sup.1', R.sup.2' and R.sup.4', which are
independent of one another, is a hydrogen atom, a halogen atom, an
alkyl group which may be substituted by halogen, or an alkoxy group
which may be substituted by halogen, R.sup.3' is a halogen atom, an
alkyl group which may be substituted by halogen, or an alkoxy group
which may be substituted by halogen, R.sup.5' is a hydrogen atom,
or an alkyl group, R.sup.6' is X.sup.7'CO-- (wherein X.sup.7' is a
hydrogen atom, or an alkyl group), or X.sup.8' OCO-- (wherein
X.sup.8' is an alkyl group), or R.sup.5' and R.sup.6' together form
.dbd.CR.sup.7' R.sup.8' (wherein R.sup.7' is a hydrogen atom, or an
alkyl group, and R.sup.8' is an amino group which may be
substituted by alkyl, or an alkoxy group), and a composition for
controlling a house insect pest, which comprises, as an active
ingredient, a hydrazone compound of the formula (II) or its
salt.
[0010] Further, the present invention provides a method for
controlling a house insect pest, which comprises applying such a
composition to its habitat.
[0011] In the above formula (I), Y includes a haloalkyl group such
as CF.sub.3, CHF.sub.2, CH.sub.2F, CF.sub.2Cl, CFCl.sub.2,
CCl.sub.3, CH.sub.2CF.sub.3, CF.sub.2CF.sub.3, CHBr.sub.2,
CH.sub.2Br or the like. Among them, a haloalkyl group having a
carbon number of from 1 to 2 and a halogen atom of from 1 to 5 is
preferable, and a trifluoromethyl group is particularly
preferable.
[0012] In the formula (I), examples of a secondary substituent of a
substituted or unsubstituted alkyl group defined as R.sup.1,
R.sup.2, R.sup.3, R.sup.4, R.sup.7, R.sup.8, R.sup.9, R.sup.10,
R.sup.11, R.sup.12 or R.sup.13; a substituted or unsubstituted
alkenyl group defined as R.sup.1, R.sup.2R.sup.3, R.sup.4,
R.sup.8R.sup.9, R.sup.10, R.sup.11, R.sup.12 or R.sup.13; a
substituted or unsubstituted alkynyl group defined as R.sup.1,
R.sup.2, R.sup.3, R.sup.4, R.sup.8, R.sup.9, R.sup.12 or R.sup.13;
and a substituted or unsubstituted cycloalkyl group defined as
R.sup.1, R.sup.2, R.sup.3 or R.sup.4 included in the group
expressed by Q: 5
[0013] (hereinafter referred to as "Q.sup.1 group"), include a
halogen atom; an alkoxy group; an alkylthio group; a trialkylsilyl
group; a phenyl group; a phenyl group substituted with a halogen,
alkyl, alkoxy, nitro or haloalkyl group; a phenyl group substituted
with a phenoxy group which may be substituted with an alkoxy or
alkylthio group; a phenoxy group; a phenylthio group; an amino
group; an amino group substituted with one or two alkyl group; a
C.sub.2-6 cyclic amino group; a morpholino group; a morpholino
group substituted with an alkyl group; a 1-piperazinyl group; a
1-piperazinyl group substituted with an alkyl, phenyl, pyridyl or
trifluoromethylpyridyl group; a heterocyclic group which may be
substituted with a halogen, alkyl, alkoxy, haloalkoxy, alkylthio,
phenyl (which may be further substituted with a halogen, alkyl,
alkoxy, nitro, haloalkyl or phenoxy group), phenoxy, phenylthio,
cycloalkyl or cycloalkoxy group; a hydroxy group; a cyano group; a
cycloalkyl group; an imino group; a --C(W.sup.2)R.sup.14 group
(W.sup.2 is an oxygen atom or a sulfur atom, R.sup.14 is a hydrogen
atom; an amino group; an amino group substituted with one or two
alkyl group; an alkyl group; an alkoxy group; an alkylthio group or
an aryl group); a --OC(W.sup.2)R.sup.15 group (R.sup.15 is an aryl
group substituted with an alkyl or haloalkyl group); or an
alkylsulfonyl group. Also, when the above substituent is an imino
group, it may form an amidino group or an imidate group, together
with an amino group or an alkoxy group.
[0014] Also, other examples of a substituent of a substituted or
unsubstituted alkyl group defined as R.sup.1 or R.sup.2 included in
the Q.sup.1 group in the formula (I), include a
4-haloalkyl-3-pyridinecarboxy- amide group, a
N-methyl-4-haloalkyl-3-pyridinecarboxyamide group, a
4-haloalkyl-3-pyridinecarboxyamide-N-alkylenoxy group, and the
like.
[0015] Thus, the above compound is a dimer of a compound of the
formula (I) connected by way of an alkylene chain. In the same
manner as above, the active ingredient of the composition for
controlling a house insect pest of the present invention includes a
trimer.
[0016] Examples of a secondary substituent of a substituted or
unsubstituted aryl group defined as R.sup.1, R.sup.2, R.sup.3,
R.sup.4, R.sup.8, R.sup.9, R.sup.12 or R.sup.13 included in the Q1
group in the formula (I), include a halogen atom; an alkyl group; a
haloalkyl group; an alkoxy group; a haloalkoxy group; an alkylthio
group; a cycloalkyl group; a cycloalkoxy group; an alkoxycarbonyl
group; an alkylcarbonyl group; an alkylcarbonyloxy group; an aryl
group; an aryloxy group; an arylthio group; an amino group; an
amino group substituted with 1 or 2 alkyl group; a cyano group; a
nitro group; a hydroxy group; and the like.
[0017] Examples of a secondary substituent of a substituted or
unsubstituted heterocyclic group defined as R.sup.4, R.sup.8,
R.sup.9, R.sup.10, R.sup.11, R.sup.12 or R.sup.13 included in the
Q.sup.1 group in the formula (I), include a halogen atom; an alkyl
group; an alkoxy group; a haloalkoxy group; an alkylthio group; a
phenyl group which may be substituted with a halogen, alkyl,
alkoxy, nitro, haloalkyl or phenoxy group; a phenoxy group; a
phenylthio group; a cycloalkyl group; a cycloalkoxy group; and the
like.
[0018] Examples of an alkyl moiety or an alkyl group included in
the Q.sup.1 group in the formula (I) include a group having a
carbon number of from 1 to 6 such as a methyl group, an ethyl
group, a propyl group, a butyl group, a pentyl group, a hexyl group
and the like, and a group having a carbon number of at least 3 may
include a linear or branched chain structure isomer. Examples of an
alkenyl group included in the Q.sup.1 group in the formula (I)
include a group having a carbon number of from 2 to 6 such as an
ethenyl group, a propenyl group, a butenyl group, a pentenyl group,
a hexenyl group and the like, and a group having a carbon number of
at least 3 may include a linear or branched chain structure isomer.
Examples of an alkynyl group included in the Q.sup.1 group in the
formula (I) include a group having a carbon number of from 2 to 6
such as an ethynyl group, a propynyl group, a butynyl group, a
pentynyl group, a hexynyl group, and a group having a carbon number
of at least 4 may include a linear of branched chain structure
isomer. Examples of a cycloalkyl group included in the Q.sup.1
group in the formula (I) include a group having a carbon number of
from 3 to 8 such as a cyclopropyl group, a cyclobutyl group, a
cyclopentyl group or a cyclohexyl group.
[0019] Examples of a C.sub.4-C.sub.5 5-membered or 6-membered
heterocyclic group which may contain a nitrogen atom or an oxygen
atom, formed from R.sup.1 and R.sup.2 together with an adjacent
nitrogen atom, included in the Q.sup.1 group in the formula (I),
include a morpholino group, a pyrrolidino group, a piperidino
group, a 1-imidazolidinyl group, a
2-cyanoimino-3-methyl-1-imidazolidinyl group, a 1-piperazinyl group
or a 4-methyl-1-piperazinyl group.
[0020] Examples of an aryl group included in the Q.sup.1 group in
the formula (I) include a phenyl group, a thienyl group, a furanyl
group, a pyridyl group, a naphthyl group, a benzothienyl group, a
benzofuranyl group, a quinolinyl group and the like.
[0021] Examples of a heterocyclic moiety of a substituted or
unsubstituted heterocyclic group included in the Q.sup.1 group in
the formula (I) include a 5 to 7-membered monocyclic or
phenyl-condensed cyclic group containing 1 to 3 hetero atoms
selected from a nitrogen atom, an oxygen atom and a sulfur atom,
such as a pyridyl group, a thienyl group, a furyl group, a
pirazinyl group, a pyrimidinyl group, a tetrahydrofuranyl group, a
thiazolyl group, an isooxazolyl group, a quinolyl group, a
pyrazolyl group, an oxazolyl group, an oxadiazolyl group, a
thiadiazolyl group, a triazolyl group and the like.
[0022] Examples of a heterocyclic moiety of a substituted or
unsubstituted heterocyclic group represented by Q in the formula
(I) include preferably a 5 to 7-membered monocyclic group
containing 2 to 3 hetero atoms selected from a nitrogen atom, an
oxygen atom and a sulfur atom, such as a 5-membered monocyclic
group including a pyrazolyl group, an oxazolyl group, a thiazolyl
group, an oxydiazolyl group, a thiadiazolyl group, a triazolyl
group and the like; and a 6-membered monocyclic group such as:
6
[0023] Examples of a secondary substituent of a substituted or
unsubstituted heterocyclic group expressed by Q in the formula (I)
include a halogen atom, a nitro group, a substituted or
unsubstituted alkyl group, a substituted or unsubstituted alkenyl
group, a substituted or unsubstituted alkynyl group, a substituted
or unsubstituted aryl group, a substituted or unsubstituted
heterocyclic group, a substituted or unsubstituted cycloalkyl
group, a hydroxyl group, a substituted or unsubstituted alkoxy
group, a substituted or unsubstituted alkenyloxy group, a
substituted or unsubstituted alkynyloxy group, a substituted or
unsubstituted aryloxy group, a substituted or unsubstituted
heterocyclicoxy group, a substituted or unsubstituted cycloalkoxy
group, a mercapto group, a substituted or unsubstituted alkylthio
group, a substituted or unsubstituted alkenylthio group, a
substituted or unsubstituted alkynylthio group, a substituted or
unsubstituted arylthio group, a substituted or unsubstituted
heterocyclicthio group, a substituted or unsubstituted
cycloalkylthio group, a substituted or unsubstituted carbonyl
group, a substituted or unsubstituted alkoxycarbonyl group, a
substituted or unsubstituted arylcarbonyl group, a substituted or
unsubstituted carbonyloxy group, a formyl group, a substituted or
unsubstituted ester group, a substituted or unsubstituted acyl
group, a substituted or unsubstituted sulfonyl group, a substituted
or unsubstituted sulfyl group, a substituted or unsubstituted
sulfonyloxy group, a substituted or unsubstituted alkylsulfyl
group, a substituted or unsubstituted sulfonylalkyl group, a
substituted or unsubstituted amino group, a substituted or
unsubstituted isocyanate group, a substituted or unsubstituted
arylalkyl group, a substituted or unsubstituted heterocyclic alkyl
group, and the like.
[0024] Among these secondary substituents, some substituents may
further be substituted with a tertiary substituent such as a
halogen atom; a cyano group; an alkyl group which may be
substituted with halogen, haloalkyl, cyano, alkoxy or aryl; an
alkoxy group which may be substituted with halogen or aryl; a
hydroxyl group; an amino group which may be substituted with
alkylsulfonyl, arylalkyl, heterocyclic alkyl, alkyl, aryl,
alkylaryl, alkylhydroxy, cyanoalkyl, alkynyl, alkenyl or
cycloalkyl; a carbonyl group which may be substituted with alkoxy,
alkylamino or alkyl; an alkylthio group; an aryloxy group; an
arylthio group; an aryl group which may be substituted with
halogen, haloalkoxy, alkyl or aryl; a nitro group; an
arylcarbonyloxy group which may be substituted with halogen or
nitro; a cycloalkyl group; an alkylsulfonyloxy group; an
alkylcarbonyloxy group; an isocyanate group which may be
substituted with alkyl, haloalkyl, alkenyl, alkynyl, heterocyclic
alkyl, aryloxy, aryloxyalkyl, alkoxy, alkoxycarbonylalkyl,
hydroxyalkyl, cyanoalkyl, alkoxyalkyl, alkenyl, arylalkoxy or
alkoxycarbonylalkyl; an arylalkylisocyanate group which may be
substituted with arylalkyl, halogen, alkyl or alkoxy; a
cycloalkylcarbonyloxy group; a cycloalkylisocyanate group which may
be substituted with haloalkyl; an alkynylalkylisocyanate group; an
arylisocyanate group which may be substituted with alkyl, alkoxy,
alkylthio, halogen, hydroxyl group, haloalkoxy, nitro,
halogen-substituted aryloxy or aryloxy; a heterocyclic group which
may be substituted with alkyl, alkoxy, aryl or ester; an
alkoxyisocyano group; and the like.
[0025] Examples of an alkyl moiety or an alkyl group in a secondary
substituent or a tertiary substituent of a substituted or
unsubstituted heterocyclic group expressed by Q in the formula (I),
include a group having a carbon number of from 1 to 6, such as a
methyl group, an ethyl group, a propyl group, a butyl group, a
pentyl group or a hexyl group, and a group having at least 3 carbon
atoms may be a linear or branched chain structure isomer. Examples
of an alkenyl group include a group having a carbon number of from
2 to 6, such as an ethenyl group, a propenyl group, a butenyl
group, a pentenyl group or a hexenyl group, and a group having at
least 3 carbon atoms may be a linear or branched chain structure
isomer. Examples of an alkynyl group include a group having a
carbon number of from 2 to 6, such as an ethynyl group, a propynyl
group, a butynyl group, a pentynyl group or a hexynyl group, and a
group having at least 3 carbon atoms may be a linear or branched
chain structure isomer. Examples of a cycloalkyl group include a
group having a carbon number of from 3 to 8, such as a cyclopropyl
group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl
group. Examples of an aryl group include a phenyl group, a thienyl
group, a furanyl group, a pyridyl group, a naphthyl group, a
benzothienyl group, a benzofuranyl group or a quinolinyl group.
Examples of a heterocyclic group include a 5-membered or 6-membered
monocyclic or phenyl-condensed cyclic group having 1 to 3 hetero
atoms selected from a nitrogen atom, an oxygen atom and a sulfur
atom, such as a pyridyl group, a thienyl group, a furyl group, a
pyrazinyl group, a thiazolyl group, an isooxazolyl group and a
quinolyl group and the like.
[0026] A compound of the formula (I) may form a salt with an acidic
material or a basic material, and examples of a salt with an acidic
material include an inorganic acid salt such as a hydrochloride, a
hydrobromide, a phosphate, a sulfate or a nitrate, and examples of
a salt with a basic material include an inorganic or organic base
salt such as a sodium salt, a potassium salt, a calcium salt, an
ammonium salt or a dimethylamine salt.
[0027] A compound of the formula (I) or its salt can be produced in
accordance with a method described in U.S. Pat. No. 5,360,806,
WO98/57969, or the like.
[0028] Examples of an alkyl group or an alkyl moiety included in
the formula (II) include a group having a carbon number of from 1
to 6 such as a methyl group, an ethyl group, a propyl group, a
butyl group, a pentyl group or a hexyl group, examples of an
alkenyl group or an alkenyl moiety include a group having a carbon
number of from 2 to 6 such as a vinyl group, a propenyl group, a
butenyl group, a pentenyl group or a hexenyl group, and examples of
an alkynyl group or an alkynyl moiety include a group having a
carbon number of from 2 to 6 such as an ethynyl group, a propynyl
group, a butynyl group, a pentynyl group or a hexynyl group. Such
respective groups and moieties include structural isomers of linear
and branched aliphatic chains.
[0029] Examples of a halogen atom included in the formula (II)
include a fluorine atom, a chlorine atom, a bromine atom or an
iodine atom.
[0030] A compound of the formula (II) may form a salt with an
acidic material or a basic material, and examples of a salt with an
acidic material include an inorganic acid salt such as a
hydrochloride or a sulfate, and examples of a salt with a basic
material include an inorganic or organic base salt such as a sodium
salt, a potassium salt, a calcium salt, an ammonium salt or a
dimethylamine salt.
[0031] Further, the compounds of the formula (II) have geometrical
isomers, i.e. E-form and Z-form, by virtue of the double bond of
the hydrazones. The present invention includes such isomers and
mixtures of such isomers.
[0032] In the present invention, the house insect pest is meant for
an insect pest living in a house or around it. Specifically, it
may, for example, be a termite, an ant or a cockroach. The
composition of the present invention is useful as a composition for
controlling the above-mentioned various house insect pests. It is
particularly useful as a composition for controlling a termite, a
composition for controlling an ant or a composition for controlling
a cockroach. It is most useful as a composition for controlling a
termite.
[0033] Examples of the termite which can be controlled by using the
composition of the present invention and the active ingredients,
include Mastotermitidae, Termopsidae (Zootermopsis, Archotermopsis,
Hodotermopsis, Porotermes and Stolotermes), Kalotermitidae
(Kalotermes, Neotermes, Cryptotermes, Incisitermes and
Glyptotermes), Hodotermitidae (Hodotermes, Microhodotermes and
Anacanthotermes) , Rhinotermitidae (Reticulitermes, Heterotermes,
Coptotermes and Schedolinotermes), Serritermitidae and Termitidae
(Amitermes, Drepanotermes, Hopitalitermes, Trinervitermes,
Macrotermes, Odontotermes, Microtermes, Nasutitermes,
Pericapritermes and Anoplotermes).
[0034] Particularly, types of the termite to be controlled in
Japan, include, for example, Reticulitermes speratus, Coptotermes
formosanus, Incisitermes minor, Cryptotermes domesticus,
Odontotermes formosanus, Neotermeskoshunensis, Glyptotermes
satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus,
Glyptotermes kodamai, Glyptotermes kushimensis, Hodotermopsis
japonica, Coptotermes guangzhoensis, Reticulitermes miyatakei,
Reticulitermes flaviceps amamianus, Reticulitermes sp.,
Nasutitermes takasagoensis, Pericapriterme nitobei and
Sinocapritermes mushae.
[0035] Examples of the ant which can be controlled by using the
composition of the present invention and the active ingredients,
include Brachyponera chinensis, Pheidole nodus, Crematogaster
osakensis, Crematogaster laboriosa, Formica japonica, Lasius
juponicus, Polyergus samurai, Monomorium intrudens, Monomorium
pharaonis, Tetramorium caespitum and fire ant.
[0036] Examples of the cockroach which can be controlled by using
the composition of the present invention and the active
ingredients, include Blattella germanica, Blattella nipponica,
Periplaneta fuliginosa, Periplaneta americana, Periplaneta
australasiae, Periplaneta brunnea, Blatta orientalis, Periplaneta
japonica, Periplaneta japanna, Neostylopyga rhombifolia, Hebardina
yayeyamana, Rhabdoblatta formosana, Trichoblatta pygmaea and
Panesthia angustipennis spadica.
[0037] The blend ratio for a two component mixture in the present
invention, i.e. the blend ratio of active ingredients (a) and (b),
(a) and (c), (a) and (d), (b) and (c), (b) and (d), or (c) and (d),
is from 1:1,000 to 1,000:1, preferably from 1:1,000 to 100:1, more
preferably from 1:1,000 to 50:1. The blend ratio for a three
component mixture in the present invention, i.e. the blend ratio of
active ingredients (a), (b) and (c); (a), (b) and (d); (a), (c) and
(d); or (b), (c) and (d), is such that the blend ratio of each of
the above-mentioned two component mixtures, and another component,
is from 1:1,000 to 1,000:1. The blend ratio for a four component
mixture in the present invention, i.e. the blend ratio of active
ingredients (a), (b), (c) and (d) is such that the blend ratio of
each of the above-mentioned three component mixtures, and another
component, is from 1:1,000 to 1,000:1. Further, the blend ratio of
active ingredients (a) and (b), (b) and (d), or (a) and (d) in the
present invention, is most preferably from 1:50 to 1:5, from
1:1,000 to 1:10, or from 10:1 to 50:1, respectively.
[0038] The composition of the present invention may be formulated
together with adjuvants into various forms such as emulsifiable
concentrates, suspension concentrates, wettable powders, water
soluble powders, soluble concentrates, floable, water dispersible
granules, granules, dusts, aerosols, pastes, poison bait chemicals,
gel, formulated sheet, ultra-low volume concentrates and the like,
in the same manner as in a case of conventional agricultural
chemicals, and may be used as a composition for controlling house
insect pests. Such formulations are usually composed of 0.001 to 99
parts by weight, preferably 0.01 to 95 parts by weight, more
preferably 0.01 to 80 parts by weight of an active ingredient and 1
to 99.999 parts by weight, preferably 5 to 99.99 parts by weight,
more preferably 20 to 99.99 parts by weight of adjuvants. When such
formulations are to be actually used, they may be used as they are
or after being diluted with suitable diluents such as water to a
predetermined concentration.
[0039] As the adjuvants, there may be mentioned carriers,
emulsifiers, suspending agents, dispersants, extenders, penetrating
agents, antifoaming agents, wetting agents, thickeners,
preservatives or stabilizers. They may be added as the case
requires. The carriers may be classified into solid carriers and
liquid carriers. As the solid carriers, there may be mentioned
powders of animal and plant origin, such as cellulose (including
cellulose derivative), starch, activated carbon, soybean flour,
wheat flour, wood powder, fish powder or powdered milk; or mineral
powders such as titanium dioxide, talc, kaolin, bentonite, calcium
carbonate, zeolite, diatomaceous earth, white carbon, clay or
alumina, and the like. As the liquid carriers, there may be
mentioned water; alcohols such as isopropyl alcohol or ethylene
glycol; ketones such as cyclohexanone or methyl ethyl ketone;
ethers such as dioxane or tetrahydrofuran; aliphatic hydrocarbons
such as kerosine, light oil or the like; aromatic hydrocarbons such
as xylene, trimethylbenzene, tetramethylbenzene, methylnaphthalene
or solvent naphtha; halogenated hydrocarbons such as chlorobenzene;
acid amides such as dimethylformamide; esters such as glycerine
ester of a fatty acid; nitrites such as acetonitrile;
sulfur-containing compounds such as dimethyl sulfoxide; and the
like.
[0040] The composition of the present invention may be applied to
the habitat of house insect pests. The habitat of house insect
pests, may, for example, be a trail for house insect pests, such as
an ant trail, a wood or a soil. The composition of the present
invention may be applied to the habitat of house insect pests as
formulated into e.g. a poison bait chemical, a dust, a paste or a
gel, so that it may be fed or contacted to the house insect pests,
whereby the house insect pests can be controlled. Especially, to
control termites or ants, it is advisable to adopt {circle over
(1)} a method wherein the above-mentioned poison bait chemical is
set in a baiting system, or {circle over (2)} a method wherein the
above-mentioned dust, paste, gel or the like is applied to an ant
trail or is directly coated to the damaged portion.
[0041] In an application of the composition of the present
invention to an ant trail, it is advisable to destroy a part of the
ant trail and apply the composition to the interior of the ant
trail. Further, in a case where the composition of the present
invention is to be applied to a wood or to the habitat of house
insect pests, spray treatment or coating treatment may be employed.
When the composition of the present invention formulated into a
dust, a paste, a gel or the like, is to be coated to the wood,
perforations may be formed for injection treatment through the
perforations, as the case requires.
[0042] By applying the composition of the present invention as a
poison bait chemical to an ant trail or around the ant trail, it is
possible to exterminate nests of termites or ants. For example, in
a case where an ant trail is present under floor or the like, a
part of the ant trail is broken and the composition of the present
invention is applied or injected. Otherwise, a poison bait chemical
is set around a building by utilizing the nature of termites or
ants always looking for a bait, to exterminate them by letting them
take in the composition of the present invention. If the poison
bait chemical of the composition of the present invention is
applied or set, termite workers or worker ants would eat the bait,
continue to invite other termites or ants to the bait to let them
continuously die, or termite workers or worker ants take the bait
back to their nests and give the bait to termite soldiers or
soldier ants, larvae, termite queen or queen ant, so that the
poison bait chemical containing the composition of the present
invention will be distributed in the nest and thereby to destroy
the nest. Further, the poison bait chemical may be set in a baiting
system such as a bait station, which may be set at or around an ant
trail or around a building.
[0043] The composition of the present invention may be used for
soil treatment in such a manner that a layer of the chemical is
formed at the soil surface. More specifically, for example, when a
liquid formulation is applied to e.g. under floor soil of a wood
building where human can enter, the application may be made by
means of a power sprayer, and it is particularly preferred to
primarily treat the base portion of a building where an ant trail
is likely to be formed. Further, in order to treat under floor soil
or the like where human can not enter, such as under floor for
bathroom or the front door, a method will be employed wherein a
hole is drilled, and the chemical will be injected to soil
therethrough. Otherwise, the composition of the present invention
may be applied to soil in the form of a granule or a dust.
[0044] The composition of the present invention may be formulated
into an aerosol containing the above dust. The aerosol usually
comprises the above dust and a propellant, and, if necessary, a
solvent. Such an aerosol usually contains the dust in an amount of
from 0.1 to 10 wt % and the propellant in an amount of from 20 to
90 wt %. Further, the solvent may, for example, be an ester such as
isopropyl myristate, isopropyl palmitate, isopropyl decanoate or
isopropyl laurate; or an alcohol such as ethanol or isopropyl
alcohol.
[0045] When the composition of the present invention takes a form
of a formulated sheet, it may contain the compound of the active
ingredients usually in a concentration of from 0.01 to 20 wt % in
the formulated sheet. The formulated sheet may be produced in
accordance with a conventional method by having the compounds of
the active ingredients supported on a carrier of a sheet shape such
as a cellulose sheet. For example, a solution or dispersion
containing the compounds of the active ingredients may be coated on
a cellulose paper, followed by drying to obtain a formulated sheet.
Such a solution or dispersion may be obtained by dissolving or
dispersing the compounds of the active ingredients in a suitable
solvent, but, if necessary, it can be diluted with a water
containing a surfactant or a dispersant.
[0046] When the composition of the present invention is to be used
for controlling a house insect pest, the dose of the active
ingredients may vary depending upon the application method of the
composition of the present invention, the formulation and various
other conditions, but is usually from 0.1 to 100 g/m.sup.2,
preferably from 0.5 to 20 g/m.sup.2, in the case of soil treatment,
and from 0.01 to 50 g/m.sup.2, preferably from 0.1 to 5 g/m.sup.2,
in the case of wood treatment. Further, when it is applied as a
poison bait chemical, the amount of the active ingredients is at a
level of from 0.01 to 10 g per application site.
[0047] The composition of the present invention may contain in
addition to the compounds of the active ingredients, fungicides of
e.g. organosulfur compounds, organophosphorus compounds,
organoarsenic compounds or organochlorine compounds; insecticides
of e.g. organophosphorus compounds, organochlorine compounds,
carbamates or chloronicotinyls, or various anti-biotics or one or
more other agents for controlling house insect pests. Particularly,
the composition of the present invention may contain insecticides,
such as chitin synthesis inhibitors of e.g. organophosphorus
compounds, carbamates or chloronicotinyls, or insect growth
regulators having sclerotization activities or juvenile hormone
mimic activities, or one or more termite-controlling active
components, ant-controlling active components or
cockroach-controlling active components. Further, an
organophosphorus insecticide such as Phoxim, Chlorpyrifos,
Pyridaphenthion, Fenitrothion or Propetamphos; a carbamate
insecticide such as Fenobucarb or Propoxur; a chloronicotinyl
insecticide such as Imidacloprid; or an insecticide such as
Sulfuramid or Hydramethylnon, may be particularly suitably
incorporated to the composition of the present invention.
[0048] The composition of the present invention is excellent in the
activities for controlling house insect pests and soil stability,
has preventive activities against house insect pests and has
lasting activities against house insect pests. Further, such a
composition makes it possible to reduce the dose of the chemical
and thus makes it possible to reduce health problems or problems of
environmental pollution.
BEST MODE FOR CARRYING OUT THE INVENTION
[0049] Now, some of preferred embodiments of the compositions for
controlling house insect pests according to the present invention,
will be exemplified. However, the present invention is by no means
restricted to such preferred embodiments.
[0050] Preferred compounds as the active ingredient (a) will be
given below. However, compounds which can be used as the active
ingredient (a), are not limited thereto. Further, the active
ingredient (a) is a compound which is preferred also in a case
where it is used alone as an active ingredient in a composition for
controlling a house insect pest.
[0051] (a-1) A pyridine compound of the formula (I) or its salt:
7
[0052] wherein Y, m and Q are as defined above.
[0053] (a-2) A compound or its salt of the above (a-1) wherein Q
is: 8
[0054] wherein X is an oxygen atom or a sulfur atom, R.sup.1 and
R.sup.2 are respectively independently a hydrogen atom, a
substituted or unsubstituted alkyl group, a substituted or
unsubstituted alkenyl group, a substituted or unsubstituted alkynyl
group, a substituted or unsubstituted cycloalkyl group, a
--C(W.sup.1)R.sup.3 group, a 9
[0055] or a --C(R.sup.8).dbd.NO--R.sup.9 group, or R.sup.1 and
R.sup.2 may form a .dbd.C(R.sup.10)R.sup.11 group or may form a
C.sub.4-C.sub.5 5-membered or 6-membered heterocyclic group which
may contain a nitrogen atom or an oxygen atom, together with an
adjacent nitrogen atom, and R.sup.3, R.sup.5, R.sup.6, Z, R.sup.7,
R.sup.8, R.sup.9, R.sup.10, R.sup.11, W.sup.1 and n are as defined
above.
[0056] (a-3) A compound or its salt of the above (a-1), wherein Q
is: 10
[0057] (wherein X is an oxygen atom or a sulfur atom, R.sup.1 and
R.sup.2 are respectively independently a hydrogen atom, a
substituted or unsubstituted alkyl group, a substituted or
unsubstituted alkenyl group, a substituted or unsubstituted alkynyl
group, a substituted or unsubstituted cycloalkyl group, a
--C(W.sup.1)R.sup.3 group, a --S(O).sub.nR.sup.5 group or a
--NHR.sup.6 group, or R.sup.1 and R.sup.2 may form a
.dbd.C(R.sup.10)R.sup.11 group or may form a
C.sub.4-C.sub.55-membered or 6-membered heterocyclic group which
may contain a nitrogen atom or an oxygen atom, together with an
adjacent nitrogen atom, and R.sup.3, R.sup.5, R.sup.6, W.sup.1 and
n are as defined above, and R.sup.10 and R.sup.11 are respectively
independently an alkoxy group or an alkylthio group.
[0058] (a-4) A compound or its salt of the above (a-1), wherein Q
is: 11
[0059] wherein X is an oxygen atom or a sulfur atom, R.sup.1 is a
hydrogen atom, a substituted or unsubstituted alkyl group, a
substituted or unsubstituted alkenyl group, a substituted or
unsubstituted alkynyl group, a substituted or unsubstituted
cycloalkyl group, a substituted or unsubstituted aryl group or a
--C(W.sup.1)R.sup.3 group, and R.sup.3, R.sup.4 and W.sup.1 are as
defined above.
[0060] (a-5) A compound or its salt of the above (a-2) or (a-3),
wherein X is an oxygen atom.
[0061] (a-6) A compound or its salt of the above (a-3), wherein
R.sup.1 and R.sup.2 are respectively independently a hydrogen atom,
a substituted or unsubstituted alkyl group or a --C(W.sup.1)R.sup.3
group, or R.sup.1 and R.sup.2 may form a .dbd.C(R.sup.10)R.sup.11
group, W.sup.1 is an oxygen atom or a sulfur atom, R.sup.3 is a
substituted or unsubstituted alkyl group, a substituted or
unsubstituted aryl group or an alkoxy group, and R.sup.10 and
R.sup.11 are respectively independently an alkoxy group or an
alkylthio group.
[0062] (a-7) A compound or its salt of the above (a-2), wherein
R.sup.1 is a hydrogen atom, R.sup.2 is a
--C(R.sup.8).dbd.NO--R.sup.9 group, and R.sub.8 and R.sup.9 are as
defined above.
[0063] (a-8) A compound or its salt of the above (a-2), wherein
R.sup.1 and R.sup.2 form a .dbd.C(R.sup.10)--N(R.sup.12)R.sup.13
group, and R.sup.10 is a hydrogen atom, a substituted or
unsubstituted alkyl group, a substituted or unsubstituted alkenyl
group or a substituted or unsubstituted heterocyclic group, and
R.sup.12 and R.sup.13 are as defined above.
[0064] (a-9) A compound or its salt of the above (a-2), wherein
R.sup.1 is a hydrogen atom, and R.sup.2 is 12
[0065] (wherein Z and R.sup.7 are as defined above).
[0066] (a-10) A compound or its salt of the above (a-3), wherein X
is an oxygen atom, R.sup.1 and R.sup.2 are respectively
independently a hydrogen atom, an alkyl group, an alkoxyalkyl
group, an alkylaminoalkyl group, a C.sub.2-6 cyclic aminoalkyl
group, a hydroxyalkyl group, a cyanoalkyl group, a
thiocarbamoylalkyl group, an alkylcarbonyloxyalkyl group, an
alkylcarbonyl group, an arylcarbonyl group, a
trifluoromethyl-substituted arylcarbonyl group, an
alkoxythiocarbonyl group or an alkoxycarbonyl group, or R.sup.1 and
R.sup.2 may form a .dbd.C(R.sup.10)R.sup.11 group, and R.sup.10 and
R.sup.11 are respectively an alkoxy group and an alkylthio
group.
[0067] (a-11) A compound or its salt of the above (a-1), wherein
the compound of the formula (I) is at least one member selected
from the group consisting of
N-cyanomethyl-4-trifluoromethyl-3-pyridinecarboxyamid- e (Compound
No. I-1), N-ethyl-4-trifluoromethyl-3-pyridinecarboxyamide
(Compound No. I-2), 4-trifluoromethyl-3-pyridinecarboxyamide
(Compound No. I-3), N-thiocarbamoylmethyl-4-trifluoromethyl-3-
pyridinecarboxyamide (Compound No. I-4),
N-ethoxymethyl-4-trifluoromethyl-3-pyridinecarboxyami- de (Compound
No. I-5), N-isopropylaminomethyl-4-trifluoromethyl-3-pyridine-
carboxyamide (Compound No. I-6),
N-cyanomethyl-N,N-bis(4-trifluoromethylni- cotinoyl)amine (Compound
No. 1-7), N-acetyl-N-cyanomethyl-4-trifluoromethy-
l-3-pyridinecarboxyamide (Compound No. I-8),
N-cyanomethyl-N-methyl-4-trif- luoromethylpyridine-3-carboxyamide
(Compound No. I-9), O-methyl
N-(4-trifluoromethylnicotinoyl)thiocarbamate (Compound No. I-10),
N-methyl-4-trifluoromethylpyridine-3-carboxyamide (Compound No.
I-11),
N--(N',N'-diemthylaminomethyl)-4-trifluoromethylpyridine-3-carboxyamide
(Compound No. I-12),
N-(1-piperidylmethyl)-4-trifluoromethylpyridine-3-ca- rboxyamide
(Compound No. I-13), N-cyanomethyl N-(4-trifluoromethylnicotino-
yl)aminomethylpivalate (Compound No. I-14), 0,S-dimethyl
N-(4-trifluoromethylnicotinoyl)iminoformate (Compound No. I-15),
N-hydroxymethyl-4-trifluoromethyl-3-pyridinecarboxyamide (Compound
No. I-16), N-acetyl-4-trifluoromethyl-3-pyridinecarboxyamide
(Compound No. I-17) and methyl
N-(4-trifluoromethylnicotinoyl)carbamate (Compound No. I-18) or
their 1-oxides.
[0068] (a-12) A compound or its salt of the above (a-1), wherein a
compound of the formula (I) is
N-cyanomethyl-4-trifluoromethyl-3-pyridine- carboxyamide.
[0069] (a-13) A compound or its salt of the above (a-1), wherein Q
is a substituted or unsubstituted heterocyclic group.
[0070] (a-14) A compound or its salt of the above (a-13), wherein
the heterocyclic group moiety is a 5 to 7-membered monocyclic group
having 2 to 3 hetero atoms selected from the group consisting of a
nitrogen atom, an oxygen atom and a sulfur atom.
[0071] (a-15) A compound or its salt of the above (a-13), wherein
the heterocyclic group moiety is a 5-membered monocyclic group
containing 2 to 3 hetero atoms selected from the group consisting
of a nitrogen atom, an oxygen atom and a sulfur atom.
[0072] (a-16) A compound or its salt of the above (a-15), wherein
the 5-membered monocyclic group is a pyrazolyl group, an oxazolyl
group, a thiazolyl group, an oxydiazolyl group, a thiadiazolyl
group or a triazolyl group.
[0073] (a-17) A compound or its salt of the above (a-13), wherein
the heterocyclic group moiety is a 6-membered monocyclic group
containing 2 to 3 hetero atoms selected from the group consisting
of a nitrogen atom, an oxygen atom and a sulfur atom.
[0074] (a-18) A compound or its salt of the above (a-17), wherein
the 6-membered monocyclic group is: 13
[0075] (wherein R.sup.16 is an alkyl group).
[0076] (a-19) A compound or its salt of the above (a-18), wherein
R.sup.16 is a methyl group or an isopropyl group.
[0077] Benzoylurea compounds preferred as the active ingredient (b)
will be given below. However, the active ingredient (b) is not
limited to such specific examples.
[0078] (b-1) Diflubenzuron
[0079] (b-2) Chlorfluazuron
[0080] (b-3) Teflubenzuron
[0081] (b-4) Flufenoxuron
[0082] (b-5) Triflumuron
[0083] (b-6) Hexaflumuron
[0084] (b-7) Lufenuron
[0085] (b-8) Novaluron
[0086] (b-9) Noviflumuron
[0087] As the benzoylurea compound of the active ingredient (b), it
is preferred to employ at least one compound selected from the
group consisting of Diflubenzuron, Chlorfluazuron, Hexaflumuron and
Flufenoxuron, and it is further preferred to employ Chlorfluazuron
and/or Hexaflumuron.
[0088] Now, pyrethroid compounds preferred as the active ingredient
(c) will be given below. However, the active ingredient (c) is not
limited thereto. The pyrethroid compounds have various optical
isomers, and in the present invention, active optional isomers and
their mixture may be used.
[0089] (c-1) Fenvalerate
[0090] (c-2) Permethrin
[0091] (c-3) Cypermethrin
[0092] (c-4) Deltamethrin
[0093] (c-5) Cyhalothrin
[0094] (c-6) Tefluthrin
[0095] (c-7) Ethofenprox
[0096] (c-8) Cyfluthrin
[0097] (c-9) Fenpropathrin
[0098] (c-10) Flucythrinate
[0099] (c-11) Fluvalinate
[0100] (c-12) Cycloprothrin
[0101] (c-13) Lambda-Cyhalothrin
[0102] (c-14) Pyrethrins
[0103] (c-15) Esfenvalerate
[0104] (c-16) Tetramethrin
[0105] (c-17) Resmethrin
[0106] (c-18) Protrifenbute
[0107] (c-19) Bifenthrin
[0108] (c-20) Acrinathrin
[0109] (c-21)
S-cyano(3-phenoxyphenyl)methyl(.+-.)cis/trans3-(2,2-dichloro-
ethenyl)-2,2-dimethylcyclopropane carboxylate.
[0110] As the pyrethroid compound of the active ingredient (c), it
is more preferred to employ at least one compound selected from the
group consisting of Flucythrinate, Cycloprothrin, Bifenthrin and
Acrinathrin, and it is further preferred to employ Bifenthrin.
[0111] As the hydrazone compound or its salt, as the active
ingredient (d), it is preferred to employ at least one compound or
its salt selected from the group consisting of
[4'-chloro-2-(4-trifluoromethylphenyl)acetop-
henone]N'-[1-(dimethylamino)ethylidene]hydrazone (Compound No.
II-1),
[4'-fluoro-2-(4-trifluoromethylphenyl)acetophenone]N'-[1-(dimethylamino)e-
thylidene]hydrazone (Compound No. II-2), ethyl
3-[1-(4-chlorophenyl-2-(4-t-
rifluoromethylphenyl)ethylidene]carbazate (Compound No. II-3),
[4'-chloro-2-(4-tert-butylphenyl)acetophenone]N'-[1-(dimethylamino)ethyli-
dene]hydrazone (Compound No. II-4),
[4'-fluoro-2-(4-tert-butylphenyl)aceto-
phenone]N'-[1-dimethylamino)ethylidene]hydrazone (Compound No.
II-5),
[4'-methyl-2-(4-tert-butylphenyl)acetophenone]N'-[1-(dimethylamino)ethyli-
dene]hydrazone (Compound No. II-6) and
[4'-chloro-2-(4-trifluoromethylphen-
yl)acetophenone]N'-[1-aminoethylidene]hydrazone (Compound No.
II-7). Further, the active ingredient (d) is a compound which is
also preferred in a case where it is used alone as an active
ingredient in a composition for controlling a house insect
pest.
[0112] The hydrazone compound of the formula (II) or its salt, may
be produced in accordance with the method disclosed in U.S. Pat.
No. 5,288,727.
[0113] Among compositions for controlling house insect pests of the
present invention, which contain the hydrazone compound of the
formula (II) or its salt, preferred embodiments will be given
below.
[0114] (1) A composition in the form of a poison bait chemical
which contains the hydrazone compound of the formula (II) or its
salt.
[0115] (2) The composition as defined in (1) wherein a bait log,
fresh pulp or pulp is used as the base material for the poison bait
chemical.
[0116] (3) The composition as defined in (1) wherein fresh pulp is
used as the base material for the poison bait chemical.
[0117] (4) The composition as defined in (1) wherein a bait log is
used as the base material for the poison bait chemical.
[0118] (5) The composition as defined in (1) wherein a bait log of
conifer type is used as the base material for the poison bait
chemical.
[0119] (6) The composition as defined in (5) wherein the bait log
of conifer type is one obtained by boiling a conifer in hot
water.
[0120] (7) The composition as defined in (5) or (6), wherein the
bait log of conifer type is pine.
[0121] (8) The composition as defined in (7) wherein the pine is
Japanese larch.
[0122] (9) A composition in the form of a gel which comprises the
hydrazone compound of the formula (II) or its salt, and a
water-absorptive polymer and which has a water-holding
property.
[0123] (10) A composition in the form of a dust which comprises the
hydrazone compound of the formula (II) or its salt, and a solid
carrier.
[0124] (11) A composition in the form of a soil treating agent
which contains the hydrazone compound of the formula (II) or its
salt.
[0125] Among the above embodiments, the composition for controlling
a house inset pest, which is in the form of a poison bait chemical,
will be explained. A house inset pest will not die immediately
after ingesting the poison bait chemical and will bring the poison
bait chemical into the nest. The poison bait chemical brought into
the nest will be ingested by or contacted to other house insect
pests. Consequently, it is possible to kill all of the house insect
pests which ingested or were in contact with the poison bait
chemical. The poison bait chemical is characterized by having such
an effect (an effect of spread).
[0126] A conventional quick acting agent of an organic phosphorus
type, a pyrethroid type or the like, has a repellent nature and
will not be ingested by a house insect pest. Even if it is
ingested, the house insect pest ingested it, will die immediately,
whereby no effect of spread can be expected. Accordingly, it is
common to employ a slow acting conventional agent such as a benzoyl
urea compound as the active ingredient for a poison bait chemical.
However, if a slow acting active ingredient is employed, although
the effect of spread can be obtained, it takes from 2 to 3 months
to kill the house insect pests in the entire nest, whereby the
damage during the period can not be prevented. Whereas, the
hydrazone compound of the above formula (II) or its salt has no
repellent nature against house insect pests, and further has an
adequate effect of spread, since it acts slowly as compared with
the quick acting conventional agent. Further, it is thereby
possible to extinct the nest of house insect pests in a short
period of time (within one month) as compared with the slow effect
of a poison bait chemical employing a conventional slow-acting
agent as an active ingredient, whereby the damage by the house
insect pests can be suppressed to a minimum level. Thus, the
above-mentioned embodiment (2) is characterized in that it is a
poison bait chemical of new type, which was not available
heretofore.
[0127] As the base material for a poison bait chemical, various
types may be mentioned, but a bait log, fresh pulp or pulp is
preferred. As the bait log to be used as the base material, various
types may be mentioned, but a bait log of conifer type such as
pine, cedar or Hinoki cypress, is preferred. Among them, it is
particularly preferred to employ pine. Further, among pines, it is
further preferred to employ Japanese larch. Such a conifer type
bait log is preferably a dead tree or one obtained by sufficiently
boiling it in hot water to decoct components and insect pests in
the bait log. The fresh pulp or pulp to be used as the base
material is used as a cellulose source which will be a bait for
house insect pests, particularly termites. As such pulp, KIMUTAORU
(tradename, manufactured by CRECIA Co.) or KITCHENTOWEL (tradename,
manufactured by NEPIA Co.) may, for example, be mentioned. The
weight ratio of the hydrazone compound or its salt to the base
material, is usually from 1:10,000 to 1:4, preferably from 1:1,000
to 1:9.
[0128] Among the above embodiments, the composition for controlling
a house insect pest, which is in the form of a gel, will be
explained. The gel may be applied to an ant trail as an ant
trail-treating agent or may be coated directly to a damaged portion
such as a wood. Otherwise, it may be coated on a bait wood, fresh
pulp or pulp to form a poison bait chemical, which will be used as
set in a baiting system, and it is particularly effective to use it
as coated on a wood damaged by termites. Further, it is most
effective to apply it to perforated portions of the wood damaged by
termites. The water absorptive polymer to be used for the gel, may
be used as the base material or may be contained as an additive in
the agent for controlling a house insect pest. Otherwise, it may be
used as a carrier for the agent for controlling a house insect
pest. The water absorptive polymer may also be one having been
swelled by having another component taken into the interior. The
water absorptive polymer to be used, is preferably one having a
water absorptivity of at least 10 times, preferably at least 100
times, its own weight. One having such a high water absorptivity
may, for example, be an isobutylene/maleic anhydride copolymer, a
polyacrylate polymer, a starch/polyacrylate polymer, a polyvinyl
acetate/polyacrylate polymer, a carboxymethylcellulose polymer or a
polyvinyl alcohol polymer. In a case where a water absorptive
polymer is used as the base material, its amount is preferably from
0.05 to 10 wt %, more preferably from 0.1 to 5%, in the total
weight.
[0129] Among the above embodiments, the dust will be explained. The
dust may be applied to an ant trail as an ant trail treating agent
or used as a poison bait chemical as set in a baiting system. This
dust is characterized in that the effect of spread is excellent as
compared with conventional dusts. As the solid carrier to be used
for this dust, the above-mentioned animal or plant powder, and/or a
mineral powder is preferred, and among them, cellulose and/or
titanium oxide is preferred. Here, the cellulose may be a
commercially available cellulose such as crystalline cellulose;
cellulose fiber such as pulp; a cellulose porous body such as
cellulose beads; or a cellulose derivative such as
carboxymethylcellulose or a cellulose ester. The weight ratio of
the hydrazone compound or its salt to the solid carrier is usually
from 1:10,000 to 1:4, preferably from 1:1,000 to 1:4.
[0130] Among the above embodiments, the soil treating agent will be
explained. The soil treating agent is used in the form of an
aqueous suspension, a granule, a dust or the like. For example, the
aqueous suspension is applied to soil for use. When a soil treating
agent containing the hydrazone compound or its salt at a
concentration of from 10 to 50,000 ppm, preferably from 100 to
5,000 ppm, is applied to soil at a rate of from 0.1 to 100
g/m.sup.2, preferably from 0.5 to 20 g/m.sup.2, the after effect in
soil becomes superior as compared with a conventional agent for
controlling termites by soil treatment.
[0131] Preferred embodiments will be given below with respect to
the method for controlling house insect pests by means of the
composition for controlling a house insect pest of the present
invention, but it should be understood that the present invention
is by no means restricted thereto.
[0132] (1) A method for controlling a house insect pest, which
comprises applying the composition of the present invention to the
habitat of the house insect pest.
[0133] (2) The method of (1) wherein the composition of the present
invention is fed or contacted to the house insect pest.
[0134] (3) The method of (1) or (2) wherein the habitat of the
house insect pest is soil.
[0135] (4) The method of (1) or (2) wherein the habitat of the
house insect pest is an ant trail.
[0136] (5) The method of (1) or (2) wherein the habitat of the
house insect pest is a wood.
[0137] (6) The method of (1) wherein the composition for
controlling a house insect pest is applied to an ant trail or
coated directly to a damaged portion to control termites or
ants.
[0138] (7) The method of (1) wherein the composition for
controlling a house insect pest of the present invention in the
form of a poison bait chemical, is set in a baiting system.
[0139] (8) The method of (7) wherein the baiting system is set at
or around an ant trail or around a building.
[0140] (9) The method of (7) or (8), wherein the baiting system is
a bait station.
[0141] (10) The method of (2) wherein the composition of the
present invention in the form of a dust, paste or gel, is applied
to an ant trail or coated directly to a damaged portion to control
termites or ants.
[0142] (11) The method of (10) wherein the composition of the
present invention in the form of a dust, paste or gel, is applied
to an ant trail.
[0143] (12) The method of (10) wherein the composition of the
present invention in the form of a dust, paste or gel is directly
coated to a damaged portion.
[0144] Now, the present invention will be described in further
detail with reference to Examples. However, it should be understood
that the present invention is by no means restricted to such
specific Examples.
TEST EXAMPLE 1
[0145] A filter paper having a diameter of 80 mm was placed in a
plastic Petri dish, and 1 ml of a pesticide solution having a
predetermined concentration was dropped thereon. After the
treatment, the solvent was sufficiently evaporated, and then, 1 ml
of distilled water was impregnated to the treated filter paper,
whereupon 15 termite workers and one termite soldier
(Reticulitermes speratus) were released. The plastic Petri dish was
placed in a container having wet cotton laid over the bottom, and
the container was maintained at 25.degree. C. for 13 days,
whereupon the number of dead termites in the Petri dish was
examined, and the mortality was calculated by the following
formula. The results are shown in Table 1.
Mortality (%)=(Number of dead termite workers/15 termite
workers).times.100
[0146] Further, by the Colby's formula, the theoretical value (%)
of mortality can be calculated. In a case where the actual
mortality (%) is higher than the theoretical value (%), it can be
said that the composition of the present invention has a
synergistic effect for controlling the house insect pest.
1TABLE 1 Chlorfluazuron Compound No. Mortality [theoretical value]
(%) I-1 8000 ppm 4000 ppm 2000 ppm 1000 ppm 0 ppm 200 ppm -- 93 100
80 100 100 ppm -- 80[69] 100[55] 93[33] 33 0 ppm 60 53 33 0 0
TEST EXAMPLE 2
[0147] A filter paper having a diameter of 80 mm was placed in a
plastic Petri dish, and 1 ml of a pesticide solution having a
predetermined concentration, was dropped thereon.
[0148] After the treatment, the solvent was sufficiently evaporated
and then, 1 ml of distilled water was impregnated to the treated
filter paper, whereupon 15 termite workers and one termite soldier
(Reticulitermes speratus) were released. The plastic Petri dish was
placed in a container having wet cotton laid over the bottom, and
the container was maintained at 25.degree. C. for 17 days. Then,
the number of dead termites in the Petri dish was examined, and the
mortality was calculated in the same manner as in Test Example 1.
The results are shown in Table 2.
2TABLE 2 Hexaflumuron Compound No. Mortality [theoretical value]
(%) I-1 8000 ppm 4000 ppm 2000 ppm 1000 ppm 0 ppm 200 ppm -- 100
100 100 100 100 ppm -- 67[52] 100[64] 100[64] 40 0 ppm 33 20 40 40
0
TEST EXAMPLE 3
[0149] A filter paper having a diameter of 80 mm was placed in a
plastic Petri dish, and 1 ml of a pesticide solution having a
predetermined concentration, was dropped thereon. After the
treatment, the solvent was sufficiently evaporated, and then, 1 ml
of distilled water was impregnated to the treated filter paper,
whereupon 10 termite workers (Reticulitermes speratus) were
released. The plastic Petri dish was placed in a container having
wet cotton laid over the bottom, and the container was maintained
at 25.degree. C. for 37 days, whereupon the number of dead termites
in the Petri dish was examined, and the mortality was calculated in
the same manner as in Test Example 1. The results are shown in
Table 3.
3TABLE 3 Chlorfluazuron Compound No. Mortality [theoretical value]
(%) II-2 4000 ppm 2000 ppm 1000 ppm 500 ppm 0 ppm 10 ppm 90[60]
100[60] 80[60] 100[44] 20 5 ppm 80[60] 80[55] 80[55] 60[37] 10 0
ppm 50 50 50 30 10
TEST EXAMPLE 4
[0150] A filter paper having a diameter of 80 mm was placed in a
plastic Petri dish, and 1 ml of a pesticide solution having a
predetermined concentration, was dropped thereon. After the
treatment, the solvent was sufficiently evaporated, and then, 1 ml
of distilled water was impregnated to the treated filter paper,
whereupon 10 termite workers (Reticulitermes speratus) were
released. The plastic Petri dish was placed in a container having
wet cotton laid over the bottom, and the container was maintained
at 25.degree. C. for 25 days, whereupon the number of dead termites
in the Petri dish was examined, and the mortality was calculated in
the same manner as in Test Example 1. The results are shown in
Table 4.
4 TABLE 4 Compound No. I-1 Mortality [theoretical value] (%)
Compound No. II-2 100 ppm 50 ppm 0 ppm 10 ppm 100[19] 100[10] 10 5
ppm 100[10] 70[0] 0 0 ppm 10 0 10
TEST EXAMPLE 5
[0151] A filter paper having a diameter of 80 mm was placed in a
cylindrical cup made of acrylic resin having a diameter of 80 mm
and a height of 60 mm (i.e. a cup having a hole with a diameter of
10 mm formed in the bottom and having hard plaster (Dental Stone)
set at the bottom in a thickness of 10 mm), and 1 ml of a solution
containing a sample compound in a predetermined concentration, was
dropped thereon. Then, nine termite workers and one termite soldier
(Coptotermes formosanus) were released thereon. The cup was placed
in a container having wet cotton laid over the bottom, and the
container was maintained at room temperature of 25.degree. C. for 7
days, whereupon the mortality of termites in the cup was examined.
The results are shown in Table 5.
5 TABLE 5 Sample Concentration compound (ppm) Mortality (%)
Compound No. 1,000 100 I-1 500 100 Chlorpyrifos 1,000 100 500 100
No treatment -- 0
TEST EXAMPLE 6
[0152] A filter paper having a diameter of 80 mm was placed in a
cylindrical cup made of acrylic resin having a diameter of 80 mm
and a height of 60 mm (i.e. a cup having a hole with a diameter of
10 mm formed in the bottom and having hard plaster (Dental Stone)
set at the bottom in a thickness of 10 mm), and 1 ml of a solution
containing a sample compound in a predetermined concentration, was
dropped thereon. Then, ten termite workers and one termite soldier
(Reticulitermes speratus) were released thereon. The cup was placed
in a container having wet cotton laid over the bottom, and the
container was maintained at room temperature of 25.degree. C. for 7
days, whereupon the mortality of termites in the cup was examined.
The results are shown in Table 6.
6 TABLE 6 Sample Concentration compound (ppm) Mortality (%)
Compound No. 1,000 100 I-1 Chlorpyrifos 1,000 100 No treatment --
0
TEST EXAMPLE 7
[0153] A compound solution having a predetermined concentration was
coated by a paint brush in an amount of 60 g/m.sup.2 on a
rectangular parallelepiped wood block of Japanese red pine of 20 mm
(L).times.10 mm (R).times.10 mm (T).
[0154] The treated wood block and a non-treated wood block were
dried at a temperature of 60.degree. C. for 48 hours, and their
weights (W.sub.1) were measured, and they were used as test
specimens. Such a test specimen was put into a cylindrical cup made
of acrylic resin (i.e. a cup having a hole with a diameter of 10 mm
formed in the bottom and having hard plaster (Dental Stone) set at
the bottom in a thickness of 10 mm), and 150 termite workers and 15
termite soldiers (Reticulitermes speratus) were released thereon.
The cup was placed in a container having wet cotton laid over the
bottom, and the container was maintained at room temperature of
25.degree. C. for 21 days, whereupon the mortality of termites in
the cup was examined. Further, the test specimen was taken out from
the cup, and the deposited substance was removed from the surface
of the test specimen. After drying at a temperature of 60.degree.
C. for 48 hours, it was weighed to obtain the weight (W.sub.2),
whereupon the mean weight loss of the wood block was calculated.
The results are shown in Table 7.
Mean weight loss (%) of the wood
block=(W.sub.1-W.sub.2/W.sub.1).times.100
7 TABLE 7 Mortality of Sample Concentration Mean weight termite
compound (W/V %) loss (%) workers (%) Compound 1 0 100 No. I-1 No
treatment -- 18 0
TEST EXAMPLE 8
[0155] A poison bait chemical comprising 1 g of powdered skim milk
and 1% of a sample compound obtained by treating 1 ml of an acetone
solution having a predetermined concentration and sufficiently
evaporating acetone in a constant temperature chamber of 40.degree.
C. for 20 hours, was prepared. Then, this poison bait chemical was
put into a cup together with a wet cotton, and 15 ants (Lasius
japonicus) were released, and four days later, the mortality was
examined. The results are shown in Table 8.
8 TABLE 8 Sample Bait concentration compound (%) Mortality (%)
Compound 1 86 No. I-1 No treatment -- 35
TEST EXAMPLE 9
[0156] A filter paper having a diameter of 80 mm was placed in a
cylindrical cup made of acrylic resin having a diameter of 80 mm
and a height of 60 mm (i.e. a cup having a hole with a diameter of
10 mm formed in the bottom and having hard plaster (Dental Stone)
set at the bottom in a thickness of 10 mm), and 1 ml of a solution
containing a sample compound in a predetermined concentration, was
dropped thereon. Then, ten termite workers and one termite soldier
(Reticulitermes speratus) were released thereon. The cup was placed
in a container having wet cotton laid over the bottom, and the
container was maintained at room temperature of 25.degree. C., and
5 days later and 20 days later, the mortality of termites in the
cup was examined. The results are shown in Table 9.
9 TABLE 9 Mortality (%) Concentration 5 Days 20 Days Sample
compound (ppm) later later Compound No. II-1 1000 0 100 Compound
No. II-2 1000 100 100 Compound No. II-3 1000 0 100 Compound No.
II-6 1000 70 100 Compound No. II-7 1000 100 100 No treatment -- 0
20
TEST EXAMPLE 10
[0157] A solution containing a sample compound in a predetermined
concentration was coated by a paint brush in an amount of 110.+-.10
mg on a rectangular parallelpiped wood block of Japanese red pine
(20 mm.times.10 mm.times.10 mm). The treated wood block was
naturally dried in a dark room of 25.degree. C. for 14 days. Then,
the treated wood block and a non-treated wood block were dried at a
temperature of 60.degree. C. for 72 hours, and their weights
(W.sub.1) were measured, and they were used as test specimens. Such
a test specimen was put into a cylindrical cup made of acrylic
resin (i.e. a cup having a hole with a diameter of 10 mm formed in
the bottom and having hard plaster (Dental Stone) set at the bottom
in a thickness of 10 mm), and 150 termite workers and 10 termite
soldiers (Reticulitermes speratus) were released thereon. The cup
was placed in a container having wet cotton laid over the bottom,
and the container was maintained at room temperature of 25.degree.
C. for 24 days, whereupon the mortality of termites in the cup was
examined. Further, the test specimen was taken out from the cup,
and the deposited substance was removed from the surface of the
test specimen. After drying at a temperature of 60.degree. C. for
72 hours, it was weighed to obtain the weight (W.sub.2), whereupon
the mean weight loss was calculated. The results are shown in Table
10.
10TABLE 10 Sample compound Mortality (%) Concentration Termite
Termite Mean weight (%) workers soldiers loss (%) Compound No. 0.2
100 100 2.9 II-2 No treatment 0 0 15.2
TEST EXAMPLE 11
[0158] 1 g of powdered skim milk was treated with 1 ml of an
acetone solution containing 10 mg of a sample compound and put in a
constant temperature chamber at 40.degree. C. for 20 hours to
sufficiently evaporate acetone. In this manner, a poison bait
chemical containing 1% of an active ingredient compound, was
prepared. Then, this poison bait chemical was put into a cup
together with a wet cotton, and 15 ants (Lasius japonicus) were
released. 4 Days later, the mortality was examined. The results are
shown in Table 11. Here, when the mortality 4 days later was at
least 40%, the controlling effect was rated to be positive.
11 TABLE 11 Bait concentration Controlling Sample compound (%)
effect Compound No. II-6 1 Positive No treatment -- Negative
TEST EXAMPLE 12
[0159] 1 g of feeding stuff for mice was treated with 0.5 ml of an
acetone solution containing 10 mg of a sample compound and put in a
constant temperature chamber at 40.degree. C. for 20 hours to
sufficiently evaporate acetone, whereby a poison bait chemical
containing 1% of the sample compound was prepared. Then, this
poison bait chemical was put into a cup together with a wet cotton,
and 10 ants (Priplaneta americana) were released and kept at
25.degree. C. in a breeding room, whereby the mortality was
examined as the time passed. The results are shown in Table 12.
12 TABLE 12 Mortality (%) Sample Concentration 1 Day 8 Days 48 Days
compound (%) later later later Compound No. 1 0 0 30 II-2 Compound
No. 1 0 100 100 II-3 Chlorpyrifos 1 100 100 100 No treatment -- 0 0
0
TEST EXAMPLE 13
[0160] A wood block of Japanese red pine (2 cm.times.2 cm.times.0.5
cm) subjected to boiling treatment in hot water, was immersed in a
methanol solution of a sample compound, and then, it was dried to
obtain a Japanese red pine poison bait chemical containing the
sample compound in a predetermined concentration. This poison bait
chemical was put into a cylindrical cup made of acrylic resin (i.e.
a cup having a hole with a diameter of 10 mm formed in the bottom
and having hard plaster (Dental Stone) set at the bottom in the
thickness of 10 mm), and 15 termite workers (Coptotermes
formosanus) were released thereon. The cup was placed in a
container having wet cotton laid over the bottom, and the container
was maintained at room temperature of 25.degree. C., whereby the
number of dead termites and abnormal termites in the cup was
examined as the time passed, and the mortality was calculated. The
results are shown in Table 13.
13 TABLE 13 Mortality (abnormal ratio) (%) Concen- 4 8 10 14 17 23
Sample tration Days Days Days Days Days Days compound (%) later
later later later later later Com- 0.1 73 100 100 100 100 100 pound
0.05 47 47(14) 80(7) 100 100 100 No. II-2 0.01 0 40(60) 55(45)
60(40) 100 100 0.005 0 0 0 30 30(30) 100 No treatment 0 0 0 20 20
27
TEST EXAMPLE 14
[0161] A Japanese red pine poison bait chemical prepared in the
same manner as in Test Example 13, was placed in a cylindrical cup
made of acrylic resin (i.e. a cup having a hole with a diameter of
10 mm formed in the bottom and having hard plaster (Dental Stone)
set at the bottom in a thickness of 10 mm), and 5 termite workers
(Coptotermes formosanus) starved for 3 days, were released and
permitted to ingest for 48 hours. Such bait-treated 5 alive termite
workers were transferred together with non-treated 5 termite
workers and 5 termite soldiers to a cup wherein a filter paper
containing water was placed, and they were kept at room temperature
of 25.degree. C., whereby the number of dead termite workers and
soldiers was examined as the time passed, and the mortality was
calculated by the following formula. The results are shown in Table
14.
Mortality of workers (%)=(number of dead termite workers/treated 5
termite workers+non-treated 5 termite workers).times.100
Mortality of soldiers (%)=(number of dead termite
soldiers/non-treated 5 termite soldiers).times.100
14 TABLE 14 Mortality (%) 6 Days 8 Days 15 Days Sample
Concentration later later later compound (%) TW TS TW TS TW TS
Compound 0.1 50 0 60 20 100 100 No. II-2 0.05 30 0 30 0 70 40 No
treatment 0 0 0 0 0 0 TW: Termite workers, TS: Termite soldiers
TEST EXAMPLE 15
[0162] Fresh pulp (2 cm.times.2 cm.times.0.1 cm) was immersed in a
methanol solution of a sample compound. Then, it was dried to
obtain a fresh pulp poison bait chemical containing 0.1% of the
sample compound. This poison bait chemical was placed in a
cylindrical cup made of acrylic resin (i.e. a cup having a hole
with a diameter of 10 mm formed in the bottom and having hard
plaster (Dental Stone) set at the bottom in a thickness of 10 mm),
and 20 termite workers (Reticulitermes speratus) were released
thereon. The cup was placed in a container having wet cotton laid
over the bottom, and the container was maintained at room
temperature of 25.degree. C. for 18 days, whereupon the number of
dead termites in the cup was examined, and the mortality was
calculated. The results are shown in Table 15.
15 TABLE 15 Sample Concentration compound (%) Mortality (%)
Compound No. 0.1 100 II-2 No treatment 0
TEST EXAMPLE 16
[0163] A test was carried out in the same manner as the above Test
Example 15 except that fresh pulp was changed to pulp (KIMUTAORU,
tradename, manufactured by CRECIA Co.). The results are shown in
Table 16.
16 TABLE 16 Sample compound Concentration (%) Mortality (%)
Compound No. 0.1 100 II-2 No treatment 0
TEST EXAMPLE 17
[0164] Soil was packed in a cylindrical connection section made of
an acrylic resin connecting two cups made of acrylic resin (i.e.
cups each having a hole with a diameter of 10 mm formed in the
bottom and having hard plaster (Dental Stone) set at the bottom in
a thickness of 10 mm), and 30 termite workers and 3 termite
soldiers (Coptotermes formosanus) were released to let them form an
ant trail. Then, at the center portion of the ant trail, 10 mg of a
dust prepared by mixing in a mortar 0.5 part by weight of a sample
compound and 99.5 parts by weight of cellulose powder, was placed.
This test apparatus was put into a container having wet cotton laid
over the bottom and kept at room temperature of 25.degree. C.,
whereby the number of dead termites in the cup was examined as the
time passed, and the mortality was calculated. Further, for the
purpose of comparison, a similar test was carried out with respect
to a dust containing 0.5% of fipronil (Terminal Dust, tradename,
manufactured by Aventis Crop Science Shionogi K.K.). These results
are shown in Table 17.
17 TABLE 17 Mortality (%) 6 11 15 Concentration Days Days Days
Sample compound (%) later later later Compound No. II-2 0.5 37 100
100 Terminal Dust 0.5 47 100 100 No treatment 0 0 0
TEST EXAMPLE 18
[0165] 1 mg of each dust prepared in the same manner as in Test
Example 17, was uniformly dispersed in a small size glass Petri
dish with a diameter of 45 mm, and 15 termite workers (Coptotermes
formosanus) were released and treated for dust coating. The treated
termite workers were put into a cylindrical cup made of acrylic
resin (i.e. a cup having a hole with a diameter of 10 mm formed in
the bottom and having hard plaster (Dental Stone) set at the bottom
in a thickness of 10 mm) containing a bait log, together with 10
non-treated termite workers and 10 non-treated termite soldiers.
The cup was placed in a container having wet cotton laid over the
bottom, and the container was maintained at room temperature of
25.degree. C., whereby the number of dead termites in the cup was
examined as the time passed, and the mortality was calculated by
the following formula. The results are shown in Table 18.
Mortality of termite workers (%)=(Number of dead termite workers/15
treated termite workers+10 non-treated termite
workers).times.100
Mortality of termite soldiers (%)=(Number of dead termite
soldiers/10 non-treated termite soldiers).times.100
18 TABLE 18 Mortality (%) 1 Day 8 Days 15 Days 19 Days Sample
Concentration later later later later compound (%) TW TS TW TS TW
TS TW TS Compound 0.5 0 0 4 0 52 40 100 100 No. II-2 Terminal 0.5
100 10 100 100 100 100 100 100 Dust No treatment 0 0 0 0 0 0 0 0
TW: Termite workers, TS: Termite soldiers
TEST EXAMPLE 19
[0166] A gel prepared by uniformity mixing 0.2 part by weight of
potassium solvate, 20 parts by weight of sorbitol, 3.5 parts by
weight of cross-linked product of a starch/sodium acrylate
copolymer, a predetermined amount of a sample compound and a
predetermined amount of water, was coated in an amount of 110
g/m.sup.2 on a dried rectangular parallelpiped wood block of
Japanese red pine of 20 mm (L).times.10 mm (R).times.10 mm (T).
This test specimen was put into a cylindrical cup made of acrylic
resin (i.e. a cup having a hole with a diameter of 10 mm in the
bottom and having hard plaster (Dental Stone) set at the bottom in
a thickness of 10 mm), and 20 termite workers (Coptotermes
formosanus) were released thereon. The cup was placed in a
container having wet cotton laid over the bottom, and the container
was maintained at room temperature of 25.degree. C., whereby the
number of dead termites in the cup was examined as the time passed,
and the mortality was calculated. The results are shown in Table
19.
19 TABLE 19 Mortality (%) 2 6 12 23 34 Sample Concentration Days
Days Days Days Days Compound (%) later later later later later
Compound 0.1 0 60 100 100 100 No. II-2 0.05 0 0 100 100 100 0.01 0
0 10 60 100 0.005 0 0 10 30 60 No treatment 0 0 0 0 10
TEST EXAMPLE 20
[0167] Sandy soil passed through a sieve of 20 mesh, was dried at a
temperature of 60.degree. C. to a constant weight, and 4 g of the
soil thus obtained, was packed into a cup having a diameter of 60
mm. 1 ml of a pesticide solution adjusted to a predetermined
concentration was added and thoroughly mixed, whereupon 15 termite
workers (Coptotermes formosanus) were leased. The cup was placed in
a container having wet cotton laid over the bottom, and the
container was maintained at room temperature of 25.degree. C.,
whereby the number of dead termites in the cup was examined as the
time passed, and the mortality was calculated. The results are
shown in Table 20.
20 TABLE 20 Mortality (abnormal ratio) (%) Concentration 1 Day 4
Days 11 Days Sample compound (ppm) later later later Compound No.
II-2 4000 0(100) 100 100 1000 0 73(27) 100 250 0 0(7) 100 No
treatment -- 0 0 0
TEST EXAMPLE 21
[0168] Sandy soil passed through a sieve of 20 mesh was dried at a
temperature of 60.degree. C. to a constant weight, and 12 g of the
soil thus obtained, was packed into a cup having a diameter of 60
mm. 3 ml of a pesticide solution adjusted to a predetermined
concentration, was added and sufficiently mixed, whereupon it was
maintained in a constant temperature chamber of 40.degree. C. for
95 days to carry out the weather resistance operation. After the
weather resistance operation, 10 termite workers (Reticulitermes
speratus) were released on this test soil. The cup was placed in a
container having wet cotton laid over the bottom, and the container
was maintained at room temperature of 25.degree. C. 2 Days later
and 6 days later after releasing the termites, the number of dead
termites in the cup was examined, and the mortality was
calculated.
[0169] The results are shown in Table 21.
21 TABLE 21 Mortality (abnormal weather ratio) (%) Sample
Concentration resistance 2 Days 6 Days compound (ppm) operation
later later Compound 1000 Negative 50(50) 100 No. II-2 Positive
10(15) 95 No -- 0 25 treatment
TEST EXAMPLE 22
[0170] Ants (Lasius japonicus) were put into a test tube together
with a cotton ball impregnated with 0.5 ml of a solution containing
a sample compound in a predetermined concentration and containing
10% of cane sugar. 11 Days later, the number of dead ants was
examined, and the mortality was calculated. The results are shown
in Table 22.
22 TABLE 22 Mortality (abnormal ratio) (%) 1 2 3 8 11 Sample
Concentration Day Days Days Days Days compound (ppm) later later
later later later Compound 50 30(70) 100 100 100 100 No. II-2 10 0
0(20) 40 80 100 No treatment 0 0 0 0 0
TEST EXAMPLE 23
[0171] A poison bait chemical containing a sample compound in an
amount of 0.2% (W/W) was prepared by using, as a bait base
material, skim milk to which (Lasius japonicus) showed preference.
2 g of this poison bait chemical was placed directly on an optional
ground surface distanced by about 50 cm from the gate of the ant
nest. Before, 2 days after, 3 days after and 5 days after placing
the poison bait chemical, the number of ants going out and coming
in through the gate per minute was examined. The results are shown
in Table 23.
23 TABLE 23 Number of ants in the habitat Before placing poison
bait 2 Days 3 Days 5 Days Sample compound chemical later later
later Compound No. 153 11 3 0 II-2 No treatment 25 22 24 21
TEST EXAMPLE 24
[0172] A filter paper having a diameter of 80 mm was placed in a
plastic Petri dish, and 1 ml of a pesticide solution having a
predetermined concentration was dropped thereon, whereupon 10
termite workers (Coptotermes formosanus) were released, and a cover
was put on the Petri dish. This plastic Petri dish was put in a
container having wet cotton laid over the bottom and maintained at
room temperature of 25.degree. C. On 21 or 28th day after the
treatment, the number of dead termites in the Petri dish was
examined, and the mortality was calculated in the same manner as
Test Example 1. The results are shown in Tables 24, 25 and 26.
24TABLE 24 (on 21st day after the treatment) Bifenthrin Mortality
(theoretical value) (%) Compound No. I-1 1 ppm 0.5 ppm 0.25 ppm 0
ppm 200 ppm 90(52) 80(28) 60(20) 20 100 ppm 70(52) 60(28) 30(20) 20
50 ppm 70(40) 40(10) 10(0) 0 0 ppm 40 10 0 0
[0173]
25TABLE 25 (on 21st day after the treatment) Bifenthrin Mortality
(theoretical value) (%) Compound No. II-2 1 ppm 0.5 ppm 0.25 ppm 0
ppm 20 ppm 90(76) 90(64) 80(60) 60 10 ppm 90(52) 70(28) 30(20) 20 5
ppm 70(40) 40(10) 10(0) 0 0 ppm 40 10 0 0
[0174]
26TABLE 26 (on 28th day after the treatment) Bifenthrin Mortality
(theoretical value) (%) Chlorfluazuron 1 ppm 0.5 ppm 0.25 ppm 0 ppm
2,000 ppm 70(58) 70(37) 40(30) 30 1,000 ppm 70(58) 60(37) 40(30) 30
500 ppm 50 50(28) 30(20) 20 0 ppm 40 10 0 0
INDUSTRIAL APPLICABILITY
[0175] According to the present invention, the composition
comprising at least two compounds selected from the group
consisting of a specific pyridine compound, a benzoylurea compound,
a pyrethroid compound and a specific hydrazone compound, as active
ingredients, can be used as an agent for controlling house insect
pests such as termites or ants.
[0176] Also according to the present invention, the composition
comprising a specific hydrazone compound as an active ingredient,
can be used as an agent for controlling house insect pests such as
termites or ants.
* * * * *