Attractant-ingestion stimulant preparations for Periplaneta americana L

A method of attracting Periplaneta americana L comprising positioning a composition comprising an attractant-ingestion stimulant in a location wherein it is desired to attract Periplaneta americana L, said stimulant comprising an amount of at least one compound selected from the group consisting of ar-.alpha.-tetralol, ar-.beta.-tetralol, ac-.alpha.-tetralol, .alpha.-naphthol, .beta.-naphthol and iristectorumin's alcohol effective to attract Periplaneta americana L.

BACKGROUND OF THE INVENTION 
1. Field of the Invention 
The present invention relates to attractant-ingestion stimulant 
preparations for Periplaneta americana L. 
Periplaneta americana L is a species of the cockroach which is most known 
and distributed throughout the world. In Japan, it is the largest species 
of the house cockroach which is most damage-producing. Among known methods 
of extermination of the cockroach are ones employing a tackiness plate or 
toxic bait in which an attractant-ingestion stimulant agent of the 
invention can be incorporated to enhance the exterminative effects. 
2. Description of the Prior Art 
As substances which possess attractant effects for the cockroach, there are 
known sex pheromones produced by extraction from the feces and the mid-gut 
of Periplaneta americana L, several monoterpenoid compounds (see Japanese 
Patent Laid Open Nos. 29502/1981, 30905/1981, 30940/1981, 79602/1981, 
79640/1981, 87536/1981 and others), fatty acids such as myristic acid and 
palmitic acid, esters thereof and others (see Japanese Patent Publication 
No. 320/1969). 
Extraction of the sex pheromones, however, requires a large number of the 
insect, Periplaneta americana L, and synthesis of the monoterpenoid 
compounds involves a complicated process. Moreover, the sex pheromones are 
excitable substances, and the cockroach is hardly immobilized. Also, 
activities of the sex pheromones are markedly reduced when male and 
females insects are coexisting [S. TAKAHASHI, C, KITAMURA: Appl. Ent. 
Zool. 2(3), 133-141 (1972)]. 
Fatty acids such as myristic acid and palmitic acid and esters thereof not 
only possess a low attractant activity but also produce no immobilizing or 
ingestion stimulant effect alone and need addition of starch or sugar. 
Accordingly, there have necessarily been increases not only in production 
cost but also in size of the attractants, with inconvenience in use 
associated. 
SUMMARY OF THE INVENTION 
As a result of extensive studies for providing effective cockroach 
attractants by overcoming the disadvantages of the prior art cockroach 
attractants, we have found that ar-.alpha.-tetralol, ar-.beta.-tetralol, 
ac-.alpha.-tetralol, .alpha.-naphthol, .beta.-naphthol and 
iristectorumin's alcohol, respectively alone, exert a high attractant and 
ingestion-stimulant activity specific for male Periplaneta americana L 
with decrease in activity when males and females coexist. The present 
invention has been completed on the basis of the above finding. 
This invention is concerned with attractant-ingestion stimulant 
preparations for Periplaneta americana L comprising as the active 
ingredient one or more members selected from the group consisting of 
ar-.alpha.-tetralol, ar-.beta.-tetralol, ac-.alpha.-tetralol, 
.alpha.-naphthol, .beta.-naphthol and iristectorumin's alcohol. 
These compounds have chemical names and structures as shown below: 
(1) ar-.alpha.-Tetralol 
(5,6,7,8-Tetrahydro-1-naphthol) 
##STR1## 
(2) ar-.beta.-Tetralol 
(5,6,7,8-Tetrahydro-2-naphthol) 
##STR2## 
(3) ac-.alpha.-Tetralol 
(1,2,3,4-Tetrahydro-1-naphthol) 
##STR3## 
(4) .alpha.-Naphthol 
(1-Naphthol) 
##STR4## 
(5) .beta.-Naphthol 
(2-Naphthol) 
##STR5## 
(6) Iristectorumin's alcohol 
(3,7-Dimethyl-10-isopropyl-2,6-cyclodecadien-1-ol) 
##STR6## 
All of the compounds (1)-(5) are, commercially and easily available. 
Iristectorumin's alcohol is also available by such a method as 
(a) Photo addition reaction of methylcyclobutene and D-piperitone followed 
by thermolysis, 
(b) extraction from Verbesima iatisquamata [F. Bohlman: Chem. Ber., 111, 
254-263 (1978)], or 
(c) reduction with LiAlH.sub.4 of iristectorumin A obtained from seed oil 
of Iristectorum maxim. 
As it is produced in very small quantity by the method (a) or (b), 
production by the method (c) is desirable. 
Various instrumental analyses were carried out to give the following data: 
The UV spectrum (EtOH) had an end absorption (.epsilon. 6610) at 206 nm; 
the IR spectrum (KBr) had characteristic absorptions at 3380, 1660, 1384, 
1366 and 845 cm.sup.-1 ; 
the high resolution mass spectrum had M.sup.+ of an m/z of 222 (C.sub.15 
H.sub.26 O); and 
the PMR (CCl.sub.4, 60 MHz) indicated the presence of methyl group at the 
end of isopropyl group from the absorption 3H, doublet, J=6.6 Hz 
respectively at 0.95 and 0.97 ppm. 
The attractant-ingestion stimulant preparations according to the invention 
are prepared, for example, in the following manner: 
One or more members of the above-mentioned compounds (1)-(6) are dissolved 
in an appropriate solvent, for example, a hydrophilic organic solvent such 
as acetone, methanol, ethanol, tetrahydrofuran, ethylene glycol, 
diethylene glycol or dimethylformamide; and lipophilic organic solvent 
such as benzene, chloroform, ether, methylene chloride or h-hexane or the 
like. The resulting solution is impregnated in an appropriate carrier, for 
example, filter paper, cardboard, nonwoven cloth, cotton cloth or flannel 
and dried. 
Alternatively, attractant tackiness plate, attractant insecticidal sheet or 
tape or attractant bait can be prepared by incorporating one or more 
members of the above-mentioned compounds (1)-(6) in a tackiness agent 
alone or in combination with an insecticide or in bait. 
In addition, an attractant-ingestion stimulant preparation in the form of 
an oil, emulsion, wettable powder, granule, pill, tablet, spray or the 
like by adding to one or more members of the above-mentioned compounds 
(1)-(6) an emulsifier, dispersant, penetrant, suspending agent, wetting 
agent, spreading agent, excipient, stabilizer or the like. Content of the 
above-mentioned compounds in these preparations is in the range from 0.1 
to 20%, preferably from 1 to 5% by weight. 
Actions of the attractant-ingestion stimulant preparations of the invention 
will be described below with reference to Test Examples. 
TEST EXAMPLE 1 
As test insects were used groups of 100 male and female (1:1) adults one 
month old after emergence of Periplaneta americana L, Periphaneta 
fuliginosa S, Periplaneta japonica K, Periplaneta australasiae F, 
Periplaneta brunnea B, Blatta orientalis L or Blattella germanica L. 
Test agents were the above-mentioned compounds (1)-(6). 
On the filter paper (Toyo Filter Paper No. 2) 11 cm. in diameter were drawn 
two circles each 3.5 cm.sup.2 in size at an equal distance. To one of the 
circles was applied a solution containing 1000 .mu.g. of one of the test 
compounds and to the other 1000 .mu.g. of acetone. The filter paper was 
air dried to evaporate the solvent thoroughly thereby preparing a test 
paper. 
A group of the test insects was placed individually in a cage which was a 
transparent polycarbonate vessel 35.times.30.times.18 cm. in size. The 
insects were reared under conditions of 25.degree. C. and 12L-12D (12-hour 
light period and 12-hour dark period) for orientation in the vessel, in 
which one of the test papers was then placed. After 24 hours, the test 
paper was recovered and examined for the degree of ingestion. 
The test compounds exerted attractant-ingestion stimulant activities 
specific for Periplaneta americana L. 
Results are shown in Table 1. 
TABLE 1 
__________________________________________________________________________ 
Test Insect 
Periplaneta 
Periplaneta 
Periplaneta 
Periplaneta 
Periplaneta 
Blatta 
Blattella 
Spot americana L 
fuliginosa S 
japonica K 
australasiae F 
brunnea B 
orientalis L 
germanica 
__________________________________________________________________________ 
L 
ar-.alpha.-Tetralol 
3+, 3+ --, -- 
--, -- 
--, -- --, -- 
--, -- 
--, -- 
ar-.beta.-Tetralol 
3+, 3+ --, -- 
--, -- 
--, -- --, -- 
--, -- 
--, -- 
ac-.alpha.-Tetralol 
+, + --, -- 
--, -- 
--, -- --, -- 
--, -- 
--, -- 
.alpha.-Naphthol 
3+, 3+ --, -- 
--, -- 
--, -- --, -- 
--, -- 
--, -- 
.beta.-Naphthol 
2+, 2+ -, - -, -- --, -- --, -- 
--, -- 
--, -- 
Iristectorumin's 
3+, 3+ --, -- 
--, -- 
--, -- --, -- 
--, -- 
--, -- 
alcohol 
Blank --, -- --, -- 
--, -- 
--, -- --, -- 
--, -- 
--, -- 
__________________________________________________________________________ 
(Note) 
3+: Very vigorous marks of biting passing through the filter paper. 
2+: Vigorous marks of biting. 
+: 4-10 marks of biting. 
.+-.: 2-3 marks of biting 
--: No mark of biting. 
TEST EXAMPLE 2 
As test insects were employed groups of 100 insects of the same sex and 
instar each consisting of male adults, female adults, male larvae or 
female larvae of Periplaneta americana L and groups of 100 insects of 
different sexes and instars consisting of 25 male adults, 25 female 
adults, 25 male larvae and 25 female larvae (called male and female 
coexistence group). (The adults were the ones one month after emergence 
and the larvae were the middle instar ones four months after hatchings). 
Test agents were the above-mentioned compounds (1)-(6). 
The same test procedures as in Test Example 1 were employed except that the 
amount of the test compound applied was 200 .mu.g. Degrees of ingestion 
were examined for the groups of the same sex and instar and the male and 
female coexistence groups. 
The test compounds exerted attractant-ingestion stimulant activities 
specific for male adults and larvae. There was no reduction in activity 
observed in the male and female coexistence groups. Results are shown in 
Table 2. 
TABLE 2 
______________________________________ 
Adult Larva Male/female 
Test agent 
Male Female Male Female 
coexistence 
______________________________________ 
ar-.alpha.-Tetra- 
2+, 2+ .+-., -- 
+, 2+ --, -- 
2+, 2+ 
lol 
ar-.beta.-Tetra- 
2+, 2+ .+-., -- 
2+, 2+ --, -- 
+, 2+ 
lol 
ac-.alpha.-Tetra- 
+, + --, -- +, .+-. 
--, -- 
+, + 
lol 
.alpha.-Naphthol 
2+, 2+ --, -- 2+, 2+ --, -- 
2+, 2+ 
.beta.-Naphthol 
2+, 2+ .+-., .+-. 
2+, 2+ --, -- 
+, 2+ 
Iristec- 
3+, 3+ --, -- 3+, 3+ --, -- 
3+, 3+ 
torumin's 
alcohol 
______________________________________ 
(Note) 
3+, 2+, +, .+-. and -- are the same ratings as defined in Test Example 1. 
TEST EXAMPLE 3 
As test insects were employed groups of 100 male adults of Periplaneta 
americana L one month old after emergence. 
Test compounds were oleic acid, myristic acid, lauryl alcohol, 
pentadecanol, octyl alcohol, bornyl acetate, nerol, 2-hydroxy-1-naphthoic 
acid, decaline, naphthalene, tetraline, ar-.alpha.-tetralol, 
ar-.beta.-tetralol, .alpha.-naphthol, .beta.-naphthol, 
ac-.alpha.-tetralol, iristectorumin's alcohol and acetone as well as 1:1 
mixtures thereof with sucrose. 
The same test procedures as in Test Example 1 were employed, and the test 
papers were recovered after 12-hour dark period to examine the degree of 
ingestion for each of the test compounds. 
ar-.alpha.-Tetralol, ar-.beta.-tetralol, .alpha.-naphthol, .beta.-naphthol, 
ac.alpha.-tetralol and iristectorumin's alcohol exerted 
attractant-ingestion stimulant activities specific for male adults of 
Periplaneta americana L without the addition of sucrose. 
Results are shown in Table 3. 
TABLE 3 
______________________________________ 
1:1 mixture 
Test agent Alone with sucrose 
______________________________________ 
Oleic acid .+-., .+-. 
3+, 3+ 
Myristic acid .+-., .+-. 
3+, 3+ 
Lauryl alcohol .+-., -- 2+, 2+ 
Pentadecanol --, -- 2+, 2+ 
Octyl alcohol --, -- --, -- 
Bornyl acetate --, -- --, -- 
Nerol --, .+-. .+-., + 
2-Hydroxy-1-naphthoic acid 
--, -- --, -- 
Decaline --, -- --, -- 
Naphthalene --, -- --, .+-. 
Tetraline --, -- --, -- 
ar-.alpha.-Tetralol 
3+, 3+ 3+, 3+ 
ar-.beta.-Tetralol 3+, 3+ 3+, 3+ 
.alpha.-Naphthol 3+, 3+ 3+, 3+ 
.beta.-Naphthol 2+, 2+ 2+, 2+ 
ac-.alpha.-Tetralol 
+, + +, + 
Iristectorumin's alcohol 
3+, 3+ 3+, 3+ 
Acetone --, -- .+-., + 
______________________________________ 
(Note) 
3+, 2+, +, .+-. and -- are the same ratings as defined in Test Example 1. 
TEST EXAMPLE 4 
As test insects were employed male adults one month old after emergence and 
male middle instar larvae four months old after hatching. 
Test agents were the above-mentioned compounds (1)-(6), each of which was 
impregnated in a round test paper 1 cm. in diameter at various 
concentrations in the same way as in Test Example 1. 
One piece of the round test papers was placed at the bottom of a vinyl 
chloride cup ca. 8.5 cm. in diameter and ca. 10 cm. in height, into which 
one test insect was released. 
The test paper was recovered after 12-hour dark period and examined for the 
mark of ingestion. The BR.sub.50 (.mu.g.) was determined. 
Results are shown in Table 4. 
TABLE 4 
______________________________________ 
BR.sub.50 (.mu.g.) 
Male adult of 
Male larva of 
Periplaneta 
Periplaneta 
Test agent americana L 
americana L 
______________________________________ 
ar-.alpha.-Tetralol 
2.0 12.3 
ar-.beta.-Tetralol 
2.7 12.3 
.alpha.-Naphthol 12.3 &gt;50 
.beta.-Naphthol 31.6 &gt;100 
ac-.alpha.-Tetralol 
&gt;100 &gt;100 
Iristectorumin's alcohol 
4.5 21.9 
______________________________________ 
TEST EXAMPLE 5 
Groups of 100 male adults of Periplaneta americana L one month old after 
emergence were employed as test insects. 
Test agents were the above-mentioned compounds (1)-(6) and sucrose, which 
were treated in the same way as in Test Example 1 except that various 
concentrations of application were employed for the measurement of 
activity. 
The compounds (1)-(6) had much higher ingestion-stimulant activities than 
activities of sucrose. Results are shown in Table 5. 
TABLE 5 
__________________________________________________________________________ 
Concentration (.mu.g./cm..sup.2) 
Test agent 285.7 142.9 71.4 28.6 14.3 
__________________________________________________________________________ 
ar-.alpha.-Tetralol 
3+, 3+, 3+ 
3+, 3+, 3+ 
3+, 3+, 3+ 
3+, 3+, 3+ 
2+, 2+, 2+ 
ar-.beta.-Tetralol 
3+, 3+, 3+ 
3+, 3+, 3+ 
3+, 3+, 3+ 
2+, 2+, + 
2+, +, + 
ac-.alpha.-Tetralol 
+, +, + 
+, .+-., + 
.+-., .+-., .+-. 
.+-., --, -- 
--, --, -- 
.alpha.-Naphthol 
3+, 2+, 3+ 
2+, 2+, 3+ 
2+, 2+, 2+ 
2+, +, + 
--, .+-., .+-. 
.beta.-Naphthol 
2+, 2+, + 
2+, +, + 
+, +, + 
.+-., .+-., -- 
--, .+-., -- 
Iristectorumin's alcohol 
3+, 3+, 3+ 
3+ , 3+, 3+ 
3+, 2+, 2+ 
2+, +, 2+ 
2+, +, + 
Sucrose --, .+-., -- 
--, --, -- 
--, --, -- 
--, --, -- 
--, --, -- 
__________________________________________________________________________ 
(Note) 
3+, 2+, +, .+-., and -- are the same ratings as defined in Test Example 1 
 
TEST EXAMPLE 6 
(1) The test agents were the above-mentioned compounds (1)-(6), which were 
impregnated respectively in a round filter paper (Toyo Filter Paper No. 2) 
1 cm. in diameter in an amount of 1000 .mu.g. in the same way as in Test 
Example 4 to prepare an attractant preparation. 
Attractant baits were also prepared in small granule by kneading 75 parts 
of fish meal powder, 5 parts of maltose, 5 parts of L-arabinose, 5 parts 
of oleic acid and 10 parts of rice bran with some water. 
(2) 60 male adults of Periplaneta americana L one month old after emergence 
were release in a room approximately 6 mats (ca. 10 m.sup.2) in size one 
week prior to initiation of the test and reared with sufficient bait and 
water given. 
A set of traps, Trap A with the above-mentioned round attractant 
preparation, Trap B with the above-mentioned granular attractant bait (0.7 
g.) and Trap C without the attractant, respectively mounted at the center 
of the tackiness surface of a cockroach catcher described in Japanese 
utility Model application Laid-Open No. 142679/1979, was placed in the 
room, and after 24 hours, examined for number of the cockroach caught. 
The experiment was repeated three times, and the average number of the 
caught cockroach was taken. 
Results are shown in Table 6. 
TABLE 6 
______________________________________ 
Number of the cockroach caught 
Test agent Trap A Trap B Trap C 
______________________________________ 
ar-.alpha.-Tetralol 
44 16 0 
ar-.beta.-Tetralol 
41 15 4 
.alpha.-Naphthol 
35 18 5 
.beta.-Naphthol 
32 21 7 
ac-.alpha.-Tetralol 
23 19 18 
Iristectorumin's alcohol 
36 20 4 
______________________________________ 
TEST EXAMPLE 7 
______________________________________ 
(1) (Test bait) 
ar-.alpha.-Tetralol 1 part 
Boric acid 10 parts 
Soluble starch 15 parts 
Potato starch 15 parts 
Water 59 parts 
100 parts 
(Control bait) 
Boric acid 10 parts 
Soluble starch 15 parts 
Potato starch 15 parts 
water 60 parts 
100 parts 
______________________________________ 
Granular test bait and control bait of the above-mentioned formulae were 
prepared by conventional procedures. 
(2) In rooms A and B each 6 mats (ca. 10 m.sup.2) in size were released 20 
male adults one month old after emergence and 20 male larvae four months 
old after hatching, respectively, which were reared with sufficient bait 
and water. There were placed the test bait prepared under (1) above in 
Room A and the control bait in Room B respectively at 5 spots in the same 
amount. Number of dead cockroach was counted after 5 days. 
Results are shown in Table 7. 
TABLE 7 
______________________________________ 
Number of the dead 
Percent extermination (%) 
______________________________________ 
Test bait 38 95 
Control bait 
12 30 
______________________________________ 
The attractant-ingestion stimulant preparations according to the present 
invention have attractant-ingestion stimulant activities specific for male 
cockroach Periplaneta americana L and selectively catch the male cockroach 
only thereby inhibiting fertilization of the female cockroach and 
producing high effects in extermination of the cockroach. 
The attractant-ingestion stimulant agents used in the invention have high 
attractant-ingestion stimulant activities even when employed alone. As 
there is no need of adding starch, sugar or the like in preparing the 
attractant-ingestion stimulant preparations according to the invention, 
the preparations are advantageous in low cost of production and 
convenience in use because of smaller sizes of the preparations.

The invention will be described below in embodiment with reference to the 
examples. 
EXAMPLE 1 
To ca. 200 ml. of n-hexane was added 1 g. of ar-.alpha.-tetralol. The 
mixture was well stirred by a stirrer for about 10 minutes to give a 
solution. The solution was impregnated, using an automatic dispenser, 
uniformly in a nonwoven cloth 20 cm. in width, 50 cm. in length and 0.1 
cm. in thickness which was air dried to evaporate the n-hexane. 
The impregnated cloth was cut by a cutter to pieces 0.5 cm. in width and 20 
cm. in length to prepare attractant-ingestion stimulant tapes. 
The tape can be used by mounting at the center of the tackiness plate in a 
cockroach catching vessel. 
Attractant-ingestion stimulant tapes were prepared in the same way as above 
using ar-.beta.-tatralol, ac-.alpha.-tetralol, .alpha.-naphthol, 
.beta.-naphthol or iristectorumin's alcohol. 
EXAMPLE 2 
A mixture of 10 g. of ar-.alpha.-tetralol or iristectorumin's alcohol, 100 
g. of boric acid, 150 g. of soluble starch, 150 g. of potato starch and 
590 g. of water was molded in an appropriate size to prepare a bait 
preparation. 
EXAMPLE 3 
A mixture of 4 g. of .alpha.-naphthol or iristectorumin's alcohol, 20 g. of 
white vaseline and 76 g. of permethrin was applied to a polyethylene tape 
5 cm. in width and 200 m. in length. 
The tape was cut to a size 5 cm. in width and 20 cm. in length to prepare 
an insecticidal tape. 
EXAMPLE 4 
To ca. 200 ml. of acetone were added 1 g. of ar-.beta.-tetralol and 1 g. of 
.beta.-naphthol. The mixture was thoroughly shaken to a solution. The 
solution was impregnated using a hole pipette in an amount of ca. 0.1 ml. 
in a round filter paper (Toyo Filter Paper No. 2) 3 cm. in diameter, which 
was air dried to evaporate the acetone. 
A simple cockroach trap was produced by placing one piece of the 
impregnated filter paper in a glass cylinder 13 cm. in diameter and 18 cm. 
in height inside of which had been coated with vaseline of a width of 5 
cm. 
EXAMPLE 5 
A mixture of 10 g. of ar-.alpha.-tetralol or iristectorumin's alcohol, 200 
g. of natural rubber, 780 g. of a tackifier agent and 10 g. of an 
antioxidant was thoroughly kneaded and applied using a roll to a cardboard 
9 cm. in width and 20 cm. in length which was used as a tackiness plate in 
the cockroach catching vessel.