WO1994014323A1 - Attracting and ingestion-stimulating agent for cockroach - Google Patents
Attracting and ingestion-stimulating agent for cockroach Download PDFInfo
- Publication number
- WO1994014323A1 WO1994014323A1 PCT/JP1992/001700 JP9201700W WO9414323A1 WO 1994014323 A1 WO1994014323 A1 WO 1994014323A1 JP 9201700 W JP9201700 W JP 9201700W WO 9414323 A1 WO9414323 A1 WO 9414323A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ingestion
- attracting
- cockroach
- test
- stimulating
- Prior art date
Links
- 241001674044 Blattodea Species 0.000 title claims abstract description 29
- 239000002269 analeptic agent Substances 0.000 title claims abstract description 15
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- 240000007643 Phytolacca americana Species 0.000 claims description 6
- 241000238657 Blattella germanica Species 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- 241000238662 Blatta orientalis Species 0.000 claims description 3
- 241000045552 Longidorus orientalis Species 0.000 claims 2
- 230000000694 effects Effects 0.000 abstract description 9
- 241000894007 species Species 0.000 abstract description 5
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- -1 phenothorin Chemical compound 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IQVNEKKDSLOHHK-FNCQTZNRSA-N (E,E)-hydramethylnon Chemical compound N1CC(C)(C)CNC1=NN=C(/C=C/C=1C=CC(=CC=1)C(F)(F)F)\C=C\C1=CC=C(C(F)(F)F)C=C1 IQVNEKKDSLOHHK-FNCQTZNRSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000004971 Pseudosasa japonica Species 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000037406 food intake Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- FJDPATXIBIBRIM-QFMSAKRMSA-N (1R)-trans-cyphenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 FJDPATXIBIBRIM-QFMSAKRMSA-N 0.000 description 1
- JWQYZECMEPOAPF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1=CC=C2CC(O)CCC2=C1 JWQYZECMEPOAPF-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- SGCPAUPWLDLCBN-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-2-ylmethanamine Chemical compound C1CCCC2=CC(CN)=CC=C21 SGCPAUPWLDLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XYFMGGWVGACNEC-UHFFFAOYSA-N n-carbamoyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C(=O)N)C(=O)C1=CC=CC=C1 XYFMGGWVGACNEC-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- SMKRKQBMYOFFMU-UHFFFAOYSA-N prallethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(CC#C)C(=O)C1 SMKRKQBMYOFFMU-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/02—Carbamic acids; Salts of carbamic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/002—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits
- A01N25/006—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits insecticidal
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Definitions
- the present invention relates to attracting and ingestion-stimulating agents for cockroaches.
- Cockroach is one of the sanitarily harmful insects most widely known throughout the world. In Japan, as the house cockroaches are known Periplaneata fuliginosa L. , P. japonica K. , P. americana L. , Blattella germanica L. , Blatta orientalis L. , etc.
- Tetralol, naphthol and phenol compounds and Iristectorumines' alcohol which are active ingredients of thes cockroach attracting and ingestion-stimulating agents, are sufficiently active without any additives. However, they are. often active against male P. americana L. only, and thus when appied to colonies of other species of cockroaches or colonies of female cockroaches only, they sometimes produce lower effects.
- This invention is directed to attracting and ingestion- stimulating agents for cockroach comprising as an active ingredient 5,6,7,8-tetrahydronaphthy1-2-methylammoniu N-(5,6,7,8-tetrahydronaphthy1-2-methy1)carbamate represented by the formula(I) .
- the compound represented by the formula(I) is a new compound.
- the compound of the present invention can be prepared, for example, by reacting carbon dioxide with 2-aminomethy1-5,6,7,8- tetrahydronaphthalene in an organic solvent.
- Attracting and ingestion-stimulating agents for cockroach according to the invention can be prepared, for exmaple, by dissolving the compound represented by the formula I in an appropriate solvent (for example, a hydrophilic organic solvent such as acetone, methanol, ethanol, tetrahydrofuran, ethylene glycol, diethylene glycol, or N,N-dimethylformaide, or a lipophilic organic solvent such as benzene, chloroform ether, methylene chloride, or n-hexane), then impregnating an appropriate carrier (for example paper, cardboad, non-woven cloth, or flannel) with the solution and drying off the solvent to give attracting tapes or the like.
- an appropriate carrier for example paper, cardboad, non-woven cloth, or flannel
- the active-ingredient compound according to the invention can also be used in such a form as granule, pill or tablet prepared by a conventional method using binder, excipient,
- the bait form of the active-ingredient compound according to the invention can be formulated together with an insecticidal ingredient.
- insecticidal ingredient there can be mentioned, organophophrous insectisides such as fenitorothion, pyridafenthion, pyridafetion, chlropyrifos-methyl, pyrethroids such as allethrin, deltamethrin, phenothorin, resmethrin, cyphenothrin, permethrin, ethofenprox, fenvalerate, prallethrin, carbamates such as carbaryl, propoxur, methoxydiazon, insect growth regurator compounds such as dodecadienote, oxime-ether compounds, pyriyl compounds, benzoylphenyl urea, and other insecticides such as hydramethylnon, and boric acid.
- organophophrous insectisides such as fenitor
- the cockroach bait may contain one or more conventional adjuvants.
- conentional adjuvants include puluverized grain, biscuit powder, sweetening, water, sugar, maltose, excipient, stabilizer, surfactant, plant oil, dextrin, and microcrvstalline cellulose.
- the active ingredient according to the invention extert an attracting and ingestion-stimulating activities in a very small amount so that no particular care should be taken for the 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.
- Test example 1 (Test material)
- test samples A group of the test insects was placed individually in a cage. After three days, the bait of the test material was examined for the degree of ingestion. The degree of ingestion of test materials (a) - (g) was compared with test sample (h).
- Test example 2 (Test materials)
- Test insects The same test procedure as in Test example 1 was employed except that two parts of hydramethylnone were formulated as an insecticide to give the test materials (a) - (g). (Test insects)
- test insects were employed 12 groups of Periplaneata fuliginosa L. , P. japonica K. , P.americana L. and Blattella germanica L.consisting of 30 adult cockroaches and 30 larvae cockroaches per one test material. (Test method)
- test material baits were set at five positions in each room.
- the attracting and ingestion-stimulating agents of the invention not only exhibit a potent attracting and ingestion-stimulating activities on various species of cockroach but also are highly effective in cockroach extermination even when male and female cockroaches live together.
- the attracting and ingestion-stimulating agent of the invention can also provide each of the cockroach controlling agents with fast acting effect.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Insects & Arthropods (AREA)
- Food Science & Technology (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
There are provided attracting and ingestion-stimulating agents for cockroach comprising 5,6,7,8-tetrahydronaphthy1-2-methylammonium N-(5,6,7,8-tetrahydronaphthy1-2-methyl)-carbamate as the active ingredient. The attracting and ingestion-stimulating agents for cockroach exhibit a very potent attracting and ingestion-stimulating activity in the known species of house cockorach, both male and female.
Description
DESCRIPION Attracting and ingestion-stimulating agent for cockroach
TECHNOLOGICAL FIELD
The present invention relates to attracting and ingestion-stimulating agents for cockroaches.
BACKGROUND ART
Cockroach is one of the sanitarily harmful insects most widely known throughout the world. In Japan, as the house cockroaches are known Periplaneata fuliginosa L. , P. japonica K. , P. americana L. , Blattella germanica L. , Blatta orientalis L. , etc.
In general, it is important for extermination of cockroach to possess a both an attracting activity and an ingestion-stimulating activity. We have already provided several cockroach attracting and ingestion-stimulating agents which stimulataneously possess the activities both (U.S. Patent No. 4,627,981; U.S. Patent No. 4,911,907).
Tetralol, naphthol and phenol compounds and Iristectorumines' alcohol, which are active ingredients of thes cockroach attracting and ingestion-stimulating agents, are sufficiently active without any additives. However, they are. often active against male P. americana L. only, and thus when appied to colonies of other species of cockroaches or colonies of female cockroaches only, they sometimes produce lower effects.
DISCLOSURE OF INVENTION
In order to provide more effectively attracting and
ingestion-stimulating agents for cockroaches than the prior art agents, we have investigated a variety of tetralin compounds, naphthalene compounds, benzene compounds and other heterocyclic compounds for their cockroach attracting and ingestion- stimulating activities. As a result of extensive studies on bicyclic nitrogen-containing compounds we have found that 5,6,7,8-tetrahydronathy1-2-methylammonium N-(5,6,7,8-tetra- hydronaphthyl-2-methyl)carbamate exhibit high attracting and ingestion-stimulating actions in adult P. americana and further that it has both an attracting and an intestion-stimulating actions which is highly active against many species of cockroach, and female cockroaches live together.
This invention is directed to attracting and ingestion- stimulating agents for cockroach comprising as an active ingredient 5,6,7,8-tetrahydronaphthy1-2-methylammoniu N-(5,6,7,8-tetrahydronaphthy1-2-methy1)carbamate represented by the formula(I) .
The compound represented by the formula(I) is a new compound.
The compound of the present invention can be prepared, for example, by reacting carbon dioxide with 2-aminomethy1-5,6,7,8- tetrahydronaphthalene in an organic solvent.
Attracting and ingestion-stimulating agents for cockroach according to the invention can be prepared, for exmaple, by
dissolving the compound represented by the formula I in an appropriate solvent (for example, a hydrophilic organic solvent such as acetone, methanol, ethanol, tetrahydrofuran, ethylene glycol, diethylene glycol, or N,N-dimethylformaide, or a lipophilic organic solvent such as benzene, chloroform ether, methylene chloride, or n-hexane), then impregnating an appropriate carrier (for example paper, cardboad, non-woven cloth, or flannel) with the solution and drying off the solvent to give attracting tapes or the like. The active-ingredient compound according to the invention can also be used in such a form as granule, pill or tablet prepared by a conventional method using binder, excipient, lubricant, stabilizer and others as usually employed to give a bait.
The bait form of the active-ingredient compound according to the invention can be formulated together with an insecticidal ingredient. As the typical examples of the insecticidal ingredient, there can be mentioned, organophophrous insectisides such as fenitorothion, pyridafenthion, pyridafetion, chlropyrifos-methyl, pyrethroids such as allethrin, deltamethrin, phenothorin, resmethrin, cyphenothrin, permethrin, ethofenprox, fenvalerate, prallethrin, carbamates such as carbaryl, propoxur, methoxydiazon, insect growth regurator compounds such as dodecadienote, oxime-ether compounds, pyriyl compounds, benzoylphenyl urea, and other insecticides such as hydramethylnon, and boric acid.
If desirde, the cockroach bait may contain one or more conventional adjuvants. Examples of conentional adjuvants include puluverized grain, biscuit powder, sweetening, water, sugar, maltose, excipient, stabilizer, surfactant, plant oil, dextrin, and microcrvstalline cellulose.
The active ingredient according to the invention extert an attracting and ingestion-stimulating activities in a very small amount so that no particular care should be taken for the 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 actions of the agents according to the invention will be described below in detail with reference to test examples.
Test example 1 (Test material)
The compounds used are shown in Table 1.
Table 1
(Test insect)
Groups of Periplaneata fuliginosa L. , P. japonica K. , P.americana L. and Blattella germanica L. each consisting of 100 adult male and female (1:1) cockroaches were prepared per one test material.
(Test methods)
A group of the test insects was placed individually in a cage. After three days, the bait of the test material was examined for the degree of ingestion. The degree of ingestion of test materials (a) - (g) was compared with test sample (h).
The experiment was repeated three times, and the avarage number of degree of ingestion was taken. (Test results)
Restuls are shown in Table 2.
Table 2
Test example 2 (Test materials)
The same test procedure as in Test example 1 was employed except that two parts of hydramethylnone were formulated as an insecticide to give the test materials (a) - (g). (Test insects)
As test insects were employed 12 groups of Periplaneata
fuliginosa L. , P. japonica K. , P.americana L. and Blattella germanica L.consisting of 30 adult cockroaches and 30 larvae cockroaches per one test material. (Test method)
48 rooms, approximately 6 mats in size, were used. One week before initiation of the test each room was stocked with a group of different species of the cockroach, whcih 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 of death cockroachs. (Test results)
The results are shown in Tabel 3.
Table 3
LTς_ : days within which 90 % of insect died.
1HE BEST MODE FOR CARRYING OUT THE INVENTION
Some examples of this invention will be explained as the following examples. However, this invention is not limited to these examples.
Synthetic example 1
Preparation of 5,6,7,8-tetrahydronaphthyl-2-methylammonium N-(5,6,7,8-tetrahydronaphthyl-2-methyl)carbamate
Into a solution of 1.61 g of 2-aminomethyl-5,6,7,8-tetra- hydronaphthalene dissolved in 30 ml of n-hexane, carbon dioxide was bubbled with stirring for ten minutes under cooling on ice. The product was filtrated, washed with n-hexane and dried to give 1.78 g of white crystals. m.p. 108 'C(decomp. )
Synthetic example 3
Preparation of 5,6,7,8-tetrahydronaphthyl-2-methylammonium N-(5,6,7,8-tetrahydronaphthy1-2-methy1)carbamate
1.61 g of 2-aminomethyl-5,6,7,8-tetrahydrohaphthalenen was allowed to stand in air. After Severn days the solid product was crushed in a powder. m.p. 108 *C(decomρ. )
Example 1
A mixture of 44.2 g of autho-meal, 40 g of syrup, 11.5 g of polyethylenen glycol, 0.0125 g of 5,6,7,8-tetrahydronaphthyl-2- 2-methylammonium N-(5,6,7,8-tetrahydronaphthyl-2-methyl)- carbamate, and 2.0 g of hydramethylnon, was kneaded together with some water, and the mixture was formed into small granular baits of the invention weighing about 0.7 g per granule.
Example 2
A mixture of 44.2 g of autho-meal, 40 g of syrup, 11.5 g of polyethylenen glycol, 0.025 g of 5,6,7,8-tetrahydronaphthyl-2- methylammonium N-(5,6,7,8-tetrahydronaphthyl-2-methyl)- carbamate, and 2.0 g of hydramethylnon, was kneaded together with some water, and the mixture was formed into small granular baits of the invention weighing about 0.7 g per granule.
INDUSTRIAL APPLICABILITY
The attracting and ingestion-stimulating agents of the invention not only exhibit a potent attracting and ingestion-stimulating activities on various species of cockroach but also are highly effective in cockroach extermination even when male and female cockroaches live together.
This brings about low production coast and minimize the size of the preparation for easiness on use.
The attracting and ingestion-stimulating agent of the invention can also provide each of the cockroach controlling agents with fast acting effect.
Claims
1. An attracting and ingestion-stimulating agent for cockorach comprising 5,6,7,8-tetrahydronaphthy1-2-methylammoniu N-(5,6,7, 8-tetrahydronaphthyl-2-methyl)carbamate as the active ingredient.
2. An attracting and ingestion-stimulating agent to claim 1, wherein the cockroach is Periplaneata fuliginosa L. , P.janponica K. , P.americana L. , Blattella germanica L. , or Blatta orientalis
3. An attracting and ingestion-stimulating agent to claim 2, wherein the cockroach is Periplaneata fuliginosa L. , P.janponica K. , P.americana L. , Blattella germanica L. , or Blatta orientalis L.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04182029A JP3125445B2 (en) | 1991-07-09 | 1992-07-09 | Cockroach Attraction, Feeding Stimulant |
| AU31723/93A AU3172393A (en) | 1991-07-09 | 1992-12-25 | Attracting and ingestion-stimulating agent for cockroach |
| PCT/JP1992/001700 WO1994014323A1 (en) | 1991-07-09 | 1992-12-25 | Attracting and ingestion-stimulating agent for cockroach |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26425891 | 1991-07-09 | ||
| JP04182029A JP3125445B2 (en) | 1991-07-09 | 1992-07-09 | Cockroach Attraction, Feeding Stimulant |
| PCT/JP1992/001700 WO1994014323A1 (en) | 1991-07-09 | 1992-12-25 | Attracting and ingestion-stimulating agent for cockroach |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1994014323A1 true WO1994014323A1 (en) | 1994-07-07 |
Family
ID=27306911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1992/001700 WO1994014323A1 (en) | 1991-07-09 | 1992-12-25 | Attracting and ingestion-stimulating agent for cockroach |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO1994014323A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0790499A2 (en) * | 1996-02-13 | 1997-08-20 | Siemens Aktiengesellschaft | Method for calibrating dissolved gas sensors and method for measuring the CO2 concentration in blood with such calibrating method |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4627981A (en) * | 1984-09-14 | 1986-12-09 | Taisho Pharmaceutical Co., Ltd. | Attractant-ingestion stimulant preparations for Periplaneta americana L |
| US4911907A (en) * | 1986-10-14 | 1990-03-27 | Taisho Pharmaceutical Co., Ltd. | Cockroach attractants |
| CA2089172A1 (en) * | 1990-08-09 | 1992-02-10 | Kazumasa Ogino | Attracting and ingestion-stimulating agent for cockroach |
| WO1992013449A1 (en) * | 1991-02-07 | 1992-08-20 | The Dow Chemical Company | Alkylthioethanamine carbamic acid derivatives and their use in biocidal compositions |
| WO1993002554A1 (en) * | 1991-08-09 | 1993-02-18 | Taisho Pharmaceutical Co., Ltd. | Attracting and ingestion-stimulating agent for cockroach |
-
1992
- 1992-12-25 WO PCT/JP1992/001700 patent/WO1994014323A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4627981A (en) * | 1984-09-14 | 1986-12-09 | Taisho Pharmaceutical Co., Ltd. | Attractant-ingestion stimulant preparations for Periplaneta americana L |
| US4911907A (en) * | 1986-10-14 | 1990-03-27 | Taisho Pharmaceutical Co., Ltd. | Cockroach attractants |
| CA2089172A1 (en) * | 1990-08-09 | 1992-02-10 | Kazumasa Ogino | Attracting and ingestion-stimulating agent for cockroach |
| WO1992013449A1 (en) * | 1991-02-07 | 1992-08-20 | The Dow Chemical Company | Alkylthioethanamine carbamic acid derivatives and their use in biocidal compositions |
| WO1993002554A1 (en) * | 1991-08-09 | 1993-02-18 | Taisho Pharmaceutical Co., Ltd. | Attracting and ingestion-stimulating agent for cockroach |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0790499A2 (en) * | 1996-02-13 | 1997-08-20 | Siemens Aktiengesellschaft | Method for calibrating dissolved gas sensors and method for measuring the CO2 concentration in blood with such calibrating method |
| EP0790499A3 (en) * | 1996-02-13 | 2001-10-10 | Siemens Aktiengesellschaft | Method for calibrating dissolved gas sensors and method for measuring the CO2 concentration in blood with such calibrating method |
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