Note: Descriptions are shown in the official language in which they were submitted.
- 1 -
DESCRIPT~ON
Attracting and ingestion-stimulating agent for cockroach
TECHNICAL FIELD
The presen~ invention relates to attracting and
ingestion-stimulating agents for coc~roaches.
BACKGROUN~ ART
Cockroach is one of the sanitarily harmful insects most
widely known throughout th,e world.
In Japan, as the ~ouse cockroach are known Periplaneta
fuliginosa S., P.jsponica K., P.americana L., Blattells
germanic L., etc.
In general, it is important for extermination of cockroach
to possess both an attracting activity and an
ingestion-stimulating acti~ity.
, We have already provided several cockroa~h attracting and
inges~ion-stimulating ~gents which stimulataneously possess
the activities both (USP 4,627,981; USP 4,911,907).
Te~ralol, naphthol and phenol compounds and 3,7-dimethyl-10-
isopropyl-2,6-cyclodecadien-1-ol, which are active ingredients of
these cockroach attracting and inges~ion-stimulating agents, are
suiciently active without any additives. Howe~er, they ~re
oten actiYe against male P.americana L. only, and thus when
applie~ to colonies of other species of cockroach or
WO ~3/02554 2 ~ ~ 3 ~ PCI~/JP92/00795
-- 2 ~-- .
colonies of female cockroach only, they sometim~s produce
lower effects.
DISCLOSURE OF INVENTION
In order ~o provide more effectively attracting and
ingestion-stim~lating agen~s for cockro~ch than the prior art
agents, we have investigated a composition comprising;
(a)one or more compounds selected from ~he group of
l-amino-5,6,7,8-te~rahydronaphthalene, 2-amino-5,6,7,8-
tetrahydronaphthalene, 2-aminomethyl-5,6,7,8-~etrahydro-
naphthalene and a salt thereof ; and
(b)one or more compounds selected from the group of
p-n-butylphenol, p-n-amylphenol, 5,6,7,8-tetrahydro-1-
naphtyhol and 5,6,7,8-tetrahydro-2-naphthol show a hight
attrac~an~ and ingestion-stimulating activity for cockroach.
A more preferred agent for cockroach of the invention is
concerned with a attracting and ingestion-s~imulating agent
for cockroach comprising as active ingredien~s a co~pound
selected from the group consis~ing of 1-amino-5,6,7,8-
tetrahydronaphthalene, 2-amino-5,6,7,8-tetrahydronsphthalene,
2-aminomethyl-5,6,7,8-~etrahydronaphth~lene a~d a salt
~hereof, and a compound selected from the group consisting of
p-n-~mylphenol, p-n-butylphenol, 5,6,7,8-tetrshydro-1-
nap~thol and 5,6,7,8-tetrahydro-2-n~phthol.
w093/û25s4 2 1 1 ~ 3 ~ ~ PCT/JP92/007g5
_ 3 _
~..t, . ~ . .
All of the com~ound are known compounds.
l-Amino-5,6,7,8-tetrahydronaphthalene, 2-amino-5,6,7,8-
tetrahydronaphthalene and 2-aminomethyl-5,6,7,8-tetrahydro-
naphthalene are disclosed, for example, in the litera~ure
cited below.
V.S. Misara et al., J.Indian Chem. Soc., 1985, 36, 803
S.W. Fenton et al., J.Am.Chem. Soc., 1955, 77, 979
V.Grinsteins et al., Lav.RSR Zinat.Akad.Ve~tis,Kim.~er.,
lg67, 7, 12
As the salt of the compo~nds, there can be mentioned, for
example, hydrochloric acid salt, oxalic acid salt, citric acid
salt, acetic acid salt, phosphoric acid salt, malonic acid
salt, sulfric acid salt~ tartaric acid salt, maleic acid salt,
lactic acid salt and pyrophosphoric acid salt.
2-Aminomethyl-5,6,7,8-tetrahydronaphthalene is allow to
stand in air to give a salt.
The salt comp~und has a chemical structure as shown ~elo~;
C H2 NH 3~)
~ C H 2 N H C 0
Howe~er, none of l-~mino-5,6,7,8-tetr~hydronaphthslene
2-amino-5,6,7,8-tetrahydronaphthalene ~nd 2-aminomethyl-
21153'1~
5,6,7,8-tetrahydronaphthalene are known for their cockroach
attracting and ingestion-stimulating activities. p-n-Amyl-
phenol, p-n-butylphenol, 5,6,7,8-t~trahydro-1-naphthol and
5,6,7,8-tetrahydro-2-naphthol are known for their cockroach
attracting and ingestion-stimul~ting activities as describ~d
in USP 4,911,907 and USP 4,627,981.
Attracting and ingestion-stimulating agents for cockroach
according to the invention can be prepared, for example, by
dissolving these compounds in an appropriate solvent ~for
example, a hydrophilic organic solvent such as acetone,
methanol, ethanol, tetrahydrofuran, ethylene glycol,
diethylene glycol or N,N-dimethyl- formamide or lipophilic
organic solvent such as benzene, chloroform, ether, methylene
chloride or n-hexane) then impergnating ~n appropriate carrier
(or pap~r, cardboad, non-woven cloth, or flannel) with the `~
solution and drying off the solvent to give ~ttracting tapes
or the like. The acti~e-ingredient compounds according to the
invention can also be used in such a ~orm as granule, pill or
tablet prepared by a conventional method using binder,
excipient, lubricant, st~bilizer and others as usually ;
employed to give a bait.
The bait form o the active-ingredient compounds according
to the invention can be formulated together with an
insecticidal ingredient As the typical examples of the
SUB~;TITUTE SHEiE~T
211~344
insecticidal ingredient, there can be mentioned,
organophosphorous insecticides such as 0,0-dimethyl 0-4-nitro-m-
toIyl phosphorothioate, 0,0-diethyl 0-(2,3-dihydro-3-oxo-2-
phenylpyridazin-6-yl)phosphorothioate, 0-3,5,6-trichloro-2-pyridyl
0,0-dimethyl phosphorothioate, pyrethroids such as ~RS)-3-allyl-2-
methyl-4-oxocyclopent-2-enyl(lRS)cis,trans-2,2-dimethyl-3-~2-
me~hylprop-l-enyl)cyclopropanecarboxylate, (S)-a-cyano-3-phenoxy-
benzyl(lR,3R)-3-~2,2-dibromovinyl)-2,2-dimethylcyclopropane-
carboxylate, 3-phenoxybenzyl(lRs)cis~trans-2~2-dimethyl-3-(2
methylprop-l-enyl)cycloprop~necarboxylate, 5-benzyl-3-furylmethyl-
(lRS)cis,trans-2,2-dimethyl 3-~2-methyprop-1-enyl)cyclopropane- :
carboxylate, a -cyano-3-phenoxybenzyl(lRS,3SR)-(lRS,3RS)-2,~- :
dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate,
3-phenoxybenzyl(lRS)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-
cyclopropanecarboxylate, 2-~4-ethoxyphenyl)-2-methylpropyl
~-phenoxybenzyl ether, (RS)-~-cyano-3-phenoxybenzyl(RS)- a - ;:
isopropyl-4-chlorophenylacetate, (RS)-2-methyl-4-oxo-3-prop-2-
ynylcyclopent-2-enyl(IRS,3SR)-(lRS,3SR)-2,2-dimethyl-3-(2-
methylpro-I-enyl)cyclopropanecarboxylate, carbamates such as
l-naphtyl methylcarbamate, 2-isopropoxyphenyl methylcarb~mate,
dodec~dienote oxime-ether benzoylphenyl urea, insect growth
regulator compounds such as dode~adienoa~e compounds, oxime-ether
compounds, pyriyl compounds, benzoylphenyl compounds urea and
other insecticides suc~ as ~etrahydro-5~5-dimethyl-2(1H)- --
SlJ~;TlTlJTE SHE~T
.. .. . . . . . .. .. .... . . .. . .
` 21153~
5~ -
pyrimidinone-~3-(4-triflyuoromethyl)phenyl]~ 2-[4-(~rifluoro-
methyl)phenyl]ethyl~-2-propenylidene hydrazone, boric acid etc.
If desired, the cockroach bait may contain one or more
conventional adjuvants. Examples of conventional adjuvants
include pulverized grain, biscuit powder, sweetening, water,
sugar, maltose excipient, excipients, stabirizer, surfactant,
plant oil, dextrin and micro~ristallin cellulose.
The active ingredient according to the invention show an
attracting and ingestion-stimulating activity in a very small
amount so that no particular care should be taken for amount
to be used.
It is preferable, for example, that a bait would contain the
ingredient in a concentration of 0.01 % by weight or more of
whole amount.
The attracting and ingestion-stimulating action of the
~gents according to the invention will be described below in
T I ~T ~ C ~ FFT
wr~93/Q2554 211~3~ P~/JP~2/007~
detail with reference to t~st examples.
Tes~ ex~mple 1
(Test material)
A test material was prepared by ~he similar method in
example 5.
The test material ~ont~ined 0.05 % by weight of the
compound in Table 1.
~.
w0 93~û~54 2 1 1 S 3 ~ 4
-- 7
Table 1
Test m~terial Tes~ ~ompound's nalne ::
1-amiDo-5. 6. 7. 8 tetr~hyc~ona~tha1ene
b 2-~ino-5. 6. 7. 8~tetrshydr~naphth~1ene
. . _
~-aminomethyl-5. 6. 7. 8~ahydronaphchalelle
d p n-amylpherlol
. _ .
p n butylph~nol
5. 6. 7. 8tetrah~o-l~aphtl~ol
5. 6. 7. 8 tet~ahy~-2~phthol .
h ~-aminomethyl-5. 6. 7. 8~etrshydr~n~phthaler~e
5. ~. 7, 8~et~shydro-2~p~1
i l-ami~v-5.6.7.8-tetrahydrQnapbtha1ene
5.~.7.8-tetrahydrD-~-n2ph~hol
_
2-aminomethyl-5.6.7.8-tetr~hydronaphthalene
p-n-amylphe~ol
_
k 2-~mino-5.6.7.8-tetr~hydrDnaphthale~
p ~-butylphenol
. without cDmpound (as the co~tr~l)
(Test insect)
Groups of Periplaneata fuliginosa S., P.japonica K., P.
aus~rAlasiae L., P.americana L., Blattell~ germanic L., Blat~a
orientalis L. each consisting of 100 ~dult male and ~emale
. . . :
(1:1) cockroaches were prepared per one test ma~eri~ls.
(Test methods)
W~ 93/025~ à ~ 4 ~ PCI`/J~92/007~5
-- 8
A group of the test inse~ts was placed individually in a
c~ge. After three days, the bait of the test material was
examined f~r the degree of ingestion. The degree of ingestion ;
of test material~a) - (k) were compared with test material
~1). The experiment was repeated three times, and the average
number of degree of ingestion ~as taken.
(Tes~ results)
Results are shown in T~ble 2.
W~ 93/02~S4 2 i l i ~ 1 4 PCr/JP92/Q~79~
--U ~ ~ o =) o~ _ C- _ C~ o~
~ _ ._ ~ ~ _. c~ c~ ~ ~ r~
~ _ _ __ _ _ _ E
.` . ~ ~ 0 o ~ ~ C~ ~ ~ ~ ~ o
nJ _ _ ~ _ _ _ _ N N ~ N
, ~ ~o
~ _ _ _ _. ~
',~ 0 C`~ ~ ~ 0 .* ~ O .~. ~ ~ ~
O _ _ _ _ _ _ _ N ._ C`~ _. a~
Cd _ _ _ _ ~ ~
~ U~ ~ CO U~ ~ CL ~ ~ 0 'O ~ ~ _~
~ ~ ~ o ~ c~ c~ ~ c~ u~ o -
o _ _. c~ _ _ _ _ ~t~ c~ ~ ~ 3
_ ~ _ _ ~ ~
a; . E
o o ~ o ~ o C~ o Ul ~ ~ ~
~ tr~ ~ C~l c~ _ _ ~ O t`~ 00 Il) U~ :
oo _ _ C~ _ _ _ _ ~i C'~ ~ C~ ~ ':
. l~lt t H~
U~ _ U~ In ~ CO Ul 0 C`~ ~O a
0 ~ U~ U~ ~ C~ ~ _ ~ o CO
L E D ,. _ _ ~ _ -- _ _ .~: E--I
W0 93/025~i4 ` 2 1 i a `~ PCI`/JP92~00795
-- 10 -- .
Test example 2
~Test m~terials)
Th~ same test procedure as in Test example 1 were employed
except ~hat two parts of hydromethylnone was formNlated as an
insec~icide to give a test material ~A) - (L).
(Test insects)
As tes~ insects were employed 12 groups of Periplaneata
fuliginosa L., P.americana L., Blattella germanic L., Blatta
orien~alis L. consisting of 30 adult cockroar~es and 30
larvae cockroaches per one test material.
(Test method)
48 rooms~ approximately 6 ma~s in size~ were used. ~ne
week before initiation of the test each room was stocked with
a group of different species of the corkroacb, which was given
food and water.
The test material baits were set at five positions in each
'room.
Effect of the attractants was evaluated on the basis of the
number ~f dead cockroach.
(Test results)
The results are shown in Table 3.
WO 93/02!;S4 h ~ ~ PCItJP92/00795
_ _. __ _ _ ..
i ~x o r~ ~ o r~ o o ~ o I~ o ~
~ tn ~ o ~ 0 ui ~ O Ln ~ u~ ~ o 0
'c ~ ~n u~ u~ u~ u~ u~ u~ r~ ~ 0 co c~
0 ~ _ _ :`
~ o- ~ ~ 0 ~ U~ ~ U~ ~ ~ o C~ Ul C`~
_~ 0 r~ r~ r~ r~ 0 r~ ~ u~ ~ ~ _
~, _ _ _ _ _
i ~ ~ o o ~ C~) o ~ ~ I~ ~ o ~
~ U~- ~ ~ ~ C`l C~ ~ 00 ~? ~ ~ u~ _
~D ~r3 . _
o o,~ _ o 0 _ _ _ __ C~ o -u~
~ _~ 0 ~ u~ 1~ ~ O ~ 0 O` ~ 0 ~
~ -~_ _ . _ _ . _ ~.
c~ 0 ~ ~ 1~ ~ o o ~ o r~
O U~ - ~ ~ ~ ~ C~ ~0 ~ 'D u~ ~O u'~
~ ~ ~ ~ '
~ _ _ _ _ . ~ :
C~ ~ ~ C~ ~ o o 0 0 0 C~ ~ O- 0 ~ ~:
E~ ~ ~ ~ c~ ~ In U~ C'~ r~ 0 ~ ~ ~ o
~ ~ _~ _ _ _ _ _ _ C~l ~ `'
~ _ _ _ _ O
,j 4~~ ~ o co o c~ o c~ o ~ r~ o ~ .
~1 U~ -- to ~`1 ~) C~ _ N _ ~0 ~f) ~ ~0 O .:
~o ::
~ - - - - - - - -
CL ~ ~ 0 U~ ~ ~? O ~ C`l ~ C~) CO r~ ' .
f~ ~ ~ ~ ~3 N C~ ~ 'O O _ O _ O
~ _ _ _ __ ~ '
L G ~ C~) a k3 ~. ~ _ _ _, ~ _~ O
~ ~ . _
w093~0~ ~ 2 1~ a 3 ~ ~ ~CT~JPg2/007~
BEST MODE FOR CARRYING OUT THE INVENTION
Some examples of this invention will be explained as the
following examples.
However, this inYention is not limited to these examples.
Unless otherwise indicated, all par~s are by weight.
E~ample 1
A mixture of 75 parts powdery fish ~eal, 5 parts of
~altose, 5 par s of L-arabinose, 5 p8rts of oleic acid, 10
parts of rice brain oil~ 0.06 part of permethrin, 0.05 part of
p-n-butylphenol and O.03 part of 2-amino-5,6,7,8-tetrahydro- ;
naphthalene w~s kneaded together with some water, and the
mixture was formed into a small granular bait of the invention
weighing about 0 7 g per gr~nule.
Example 2
150 parts of water-soluble starch, 150 parts of potato
starch, 100 parts of boric acid 0.6 part of sodium benzoa~e,
0.2 part of dib11~ylhydroxytoluene, 0.03 part of
2-amino-5,6>7,8-tetrahydro- naphthalene, O.1 part of 5,6,7,8-
te~rahydro-l-naphthol and 599.5 parts of water were blended
~nd formed into ~ cockroach bait o~ the invention weighing
abou~ 10 g per piece.
Ex~mple 3
100 par~s of wheat powders, 35 parts of water-soluble
WO 93/025~ ) 3 ~ ~ PCl`~JP92/00795
-- 1 3 --
starch~ 35 parts of starch, one part of methoprene, 0.06 part
of sodium benzoate, 0.02 par~ of dibutylhydroxytoluPne, 0.05
p~rt of 5,6,7,8-tetrahydro-2-naphthol and 0.03 part of
2-amino-5,6,7,8- tetrahydron~phthalene hydrocarbo~ate were
blended ~ogether ~ith an appropriate amount of water and
formed in~o a cockroach bait of the in~ention weighing about 5
g per piece.
Example 4
lOO parts of corn syrup, 30 par~s of sorbitol, 14 parts of
gelatin, 48 parts of water, 2 p~rts of pyriproxyfen, 0.06 part
of sodium benzoate~ 0.02 part of dibutylhydroxytoluene,
p-n-butylphenol and 0.1 parts of 2-aminomethyl-5,6~7,8-
tetr~ydronaphthalene were blended and formed into a co~kroach
bAit of ~he invention weighing about 10 g per piece.
Example 5
40 par~s of ~hick malt syr~p, 45 parts of oats powder, 11
'p~rts of macrogol, 0.5 part of cyphenot~rin, onP part of
diflu~enæurone, 0.06 part of sodium benzoate, 0.02 part of
dibutylhydroxy~oluene, 0.05 part of p-n-amylphenol and
2-amino-5,6,7,8-tetr~hydro- naphthalene were blended ~nd
formed into a csckroach bait of the invention weighing about
10 g per piece.
Example 6
WO 93/Q~554 2 ~ ~ ~ 3 4 ~ PC~/JP92/00795
-- ~4 --
20 p~rts of brown sugar, 2 parts of corn oil, 2 parts of
chryslis powder, 20 parts of biscuit powder, 50 parts dextrin,
0.06 part of sodium benzoate, 0.02 part of
dibutylhydroxytoluene, 2 parts of hydramethylnone, 0.02 part
of p-n-amylphenol and 0.03 part of 2-amino-5,6,7,8-tetrahydro-
naphthalene were blended and formed }nto a cockroach bait of
the invention weighing about 5 g per piece.
Example 7
20 parts of powdery sugar, lO parts of corn oil~ 30 par~s
of sweet corn oii, 60 parts of crystalline cellulose, 2 parts
of e~hofenprox, 0.06 parts sodium benzoate, 0.02 part of
dibutylhydroxytoluene, 0.02 part of p-n-amylphenol ~nd 0. 03
p2rt of 2-amino-5,6,7,8-tetrahydronaphthalene were blended and
formed into a cockroach bait of the invention ~eighing about 5
g per piece.
Example 8
15 parts of miner~l oil, 2 parts of ammonium hydroxide, 2
par~s vf polyoxyethylene nonylphenyl ether, 0.5 p~rt of
carboxymethyl cellulose, 3.5 parts of potato starch, one part
of propox~r, 0.5 part of fenoxycarb, 0.06 part o~ sodium
be~ozate, 0.02 part of dibutyl~ydroxytoluene, 0.05 part of
5,6,7,8-tetrahydro-2-naphthol and 0.03 part of 2-amino-
5,6~7,8-tetrahydronapbthal~ne were blended and ormed into a
WC~ 93/02~ 3 3 1 ~ PCl`/JP92/00795
.' . - 15 -
.; . , `; :
cockroach bait of the invention weighing about 5 g per piece.
Example 9
15 parts of white mineral oil, 1.5 par~s of polyoxyethylene
glycol dioleate, 2 parts of polyoxyethyle~e nonylphenyl ether,
one part of hydroxyethyl cellulose, 0.5 part of xanthane gum,
5 parts of corn starch, 2 part5 of chloropyrifosmethyl, 0.06
part of sodium benzoate, 0.02 part of 5,6,7,8-tetrahydro-
2-n~pbthol and 0.0~ part of 2-amino-5,6,7,8-tetrahydro-
naph~halene were blended and formed into a cockroach bait of
the invention weighing about 5 g per piece.
INDUSTRIAL APPLICABILITY
The attracting and ingestion-stimulating agents o the
invention not only exhibit a potent attracting and
ingestion-stimulating activity on various species of cockroach
but also are highly effective in cockrosch extermination even
~hen m~le and female cockroaches li~e toge~her.
This brings about low productio~ ost and mini~ize the size
vf the preparation for easiness on use.
The attracting and ingestion-stimulating component of the
invention can also provide each of the cockroach controlling
agents with fast acting effect.
