US20050215597A1 - Composition for controlling house insect pest and method for controlling house insect pest - Google Patents

Composition for controlling house insect pest and method for controlling house insect pest Download PDF

Info

Publication number
US20050215597A1
US20050215597A1 US10/504,158 US50415805A US2005215597A1 US 20050215597 A1 US20050215597 A1 US 20050215597A1 US 50415805 A US50415805 A US 50415805A US 2005215597 A1 US2005215597 A1 US 2005215597A1
Authority
US
United States
Prior art keywords
group
substituted
unsubstituted
compound
atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/504,158
Other languages
English (en)
Inventor
Masayuki Morita
Osamu Imai
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ishihara Sangyo Kaisha Ltd
Original Assignee
Ishihara Sangyo Kaisha Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd
Assigned to ISHIHARA SANGYO KAISHA, LTD. reassignment ISHIHARA SANGYO KAISHA, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: IMAI, OSAMU, MORITA, MASAYUKI
Publication of US20050215597A1 publication Critical patent/US20050215597A1/en
Priority to US12/105,779 priority Critical patent/US7655677B2/en
Abandoned legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N3/00Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions; Grafting wax
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N35/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N53/00Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • 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.
  • 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.
  • organophosphorus compounds such as chlorpyrifos, or pyrethroids may, for example, be mentioned.
  • agents for controlling ants hydramethylnon, lithium sulfonate, organophosphorus compounds, carbamates, or pyrethroids
  • agents for controlling cockroaches pyrethroids or organophosphorus compounds
  • a new agent for controlling a house insect pest is desired.
  • 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: wherein Y is a haloalkyl group, m is 0 or 1, and Q is or a substituted or unsubstituted heterocyclic group, (wherein X is an oxygen atom or a sulfur atom, R 1 and R 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 1 )R 3 group, a —OR 4 group, a —S(O) n R 5 group, a —NHR 6 group, a —C(R 8 ) ⁇ NO
  • the present invention provides a method for controlling a house insect pest, which comprises applying such a composition to its habitat.
  • Y includes a haloalkyl group such as CF 3 , CHF 2 , CH 2 F, CF 2 Cl, CFCl 2 , CCl 3 , CH 2 CF 3 , CF 2 CF 3 , CHBr 2 , CH 2 Br or the like.
  • 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.
  • substituents of a substituted or unsubstituted alkyl group defined as R 1 or R 2 included in the Q 1 group in the formula (I) include a 4-haloalkyl-3-pyridinecarboxyamide group, a N-methyl-4-haloalkyl-3-pyridinecarboxyamide group, a 4-haloalkyl-3-pyridinecarboxyamide-N-alkylenoxy group, and the like.
  • the above compound is a dimer of a compound of the formula (I) connected by way of an alkylene chain.
  • the active ingredient of the composition for controlling a house insect pest of the present invention includes a trimer.
  • Examples of a secondary substituent of a substituted or unsubstituted heterocyclic group defined as R 4 , R 8 , R 9 , R 10 , R 11 , R 12 or R 13 included in the Q 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.
  • Examples of an alkyl moiety or an alkyl group included in the Q 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 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 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 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.
  • Examples of a C 4 -C 5 5-membered or 6-membered heterocyclic group which may contain a nitrogen atom or an oxygen atom, formed from R 1 and R 2 together with an adjacent nitrogen atom, included in the Q 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.
  • Examples of an aryl group included in the Q 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.
  • Examples of a heterocyclic moiety of a substituted or unsubstituted heterocyclic group included in the Q 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.
  • 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:
  • 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
  • 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
  • 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.
  • heterocyclic group examples 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.
  • a compound of the formula (I) may form a salt with an acidic material or a basic material
  • 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
  • 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.
  • 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.
  • 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
  • Examples of a halogen atom included in the formula (II) include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • a compound of the formula (II) may form a salt with an acidic material or a basic material
  • examples of a salt with an acidic material include an inorganic acid salt such as a hydrochloride or a sulfate
  • 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.
  • 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.
  • 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.
  • 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 ).
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • suitable diluents such as water to a predetermined concentration.
  • 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.
  • 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.
  • 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.
  • composition of the present invention 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 %.
  • 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.
  • the composition of the present invention 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.
  • 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.
  • 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.
  • 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 2 , preferably from 0.5 to 20 g/m 2 , in the case of soil treatment, and from 0.01 to 50 g/m 2 , preferably from 0.1 to 5 g/m 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.
  • 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.
  • fungicides e.g. organosulfur compounds, organophosphorus compounds, organoarsenic compounds or organochlorine compounds
  • insecticides e.g. organophosphorus compounds, organochlorine compounds, carbamates or chloronicotinyls, or various anti-biotics or one or more other agents for controlling house insect pests.
  • insecticides such as chitin synthesis inhibitors of e.g.
  • organophosphorus compounds 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.
  • 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.
  • compositions for controlling house insect pests will be exemplified.
  • present invention is by no means restricted to such preferred embodiments.
  • the active ingredient (a) 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.
  • Benzoylurea compounds preferred as the active ingredient (b) will be given below.
  • the active ingredient (b) is not limited to such specific examples.
  • 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.
  • pyrethroid compounds preferred as the active ingredient (c) will be given below.
  • 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.
  • 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.
  • 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)acetophenone]N′-[1-(dimethylamino)ethylidene]hydrazone (Compound No. II-1), [4′-fluoro-2-(4-trifluoromethylphenyl)acetophenone]N′-[1-(dimethylamino)ethylidene]hydrazone (Compound No.
  • 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.
  • 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.
  • the composition for controlling a house inset pest which is in the form of a poison bait chemical
  • 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).
  • 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.
  • the above-mentioned embodiment (2) is characterized in that it is a poison bait chemical of new type, which was not available heretofore.
  • KIMUTAORU tradename, manufactured by CRECIA Co.
  • KITCHENTOWEL tradename, manufactured by NEPIA Co.
  • 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.
  • the composition for controlling a house insect pest which is in the form of a gel
  • 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.
  • 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.
  • 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.
  • 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.
  • 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° C. for 7 days, whereupon the mortality of termites in the cup was examined. The results are shown in Table 6. TABLE 6 Sample Concentration compound (ppm) Mortality (%) Compound No. 1,000 100 I-1 Chlorpyrifos 1,000 100 No treatment — 0
  • 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.
  • Fresh pulp (2 cm ⁇ 2 cm ⁇ 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° C. for 18 days, whereupon the number of dead termites in the cup was examined, and the mortality was calculated.
  • Table 15 TABLE 15 Sample Concentration compound (%) Mortality (%) Compound No. 0.1 100 II-2 No treatment 0
  • 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.
  • 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
  • This test specimen was put into a cylindrical cup made of acrylic resin (i.e.
  • 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. TABLE 23 Number of ants in the habitat Before placing poison bait 2 Days 3 Days 5 Days Sample compound chemical later later later later Compound No. 153 11 3 0 II-2 No treatment 25 22 24 21
  • 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° C.
  • 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. TABLE 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
  • 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.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
US10/504,158 2002-02-22 2003-02-18 Composition for controlling house insect pest and method for controlling house insect pest Abandoned US20050215597A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/105,779 US7655677B2 (en) 2002-02-22 2008-04-18 Composition and method for controlling house insect pest

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2002045837 2002-02-22
JP2002-045837 2002-02-22
JP2002-226478 2002-08-02
JP2002226478 2002-08-02
PCT/JP2003/001711 WO2003069990A2 (en) 2002-02-22 2003-02-18 Composition and method for controlling house insect pest

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/105,779 Continuation US7655677B2 (en) 2002-02-22 2008-04-18 Composition and method for controlling house insect pest

Publications (1)

Publication Number Publication Date
US20050215597A1 true US20050215597A1 (en) 2005-09-29

Family

ID=27759678

Family Applications (2)

Application Number Title Priority Date Filing Date
US10/504,158 Abandoned US20050215597A1 (en) 2002-02-22 2003-02-18 Composition for controlling house insect pest and method for controlling house insect pest
US12/105,779 Expired - Fee Related US7655677B2 (en) 2002-02-22 2008-04-18 Composition and method for controlling house insect pest

Family Applications After (1)

Application Number Title Priority Date Filing Date
US12/105,779 Expired - Fee Related US7655677B2 (en) 2002-02-22 2008-04-18 Composition and method for controlling house insect pest

Country Status (8)

Country Link
US (2) US20050215597A1 (ja)
EP (1) EP1476017B1 (ja)
JP (1) JP4324391B2 (ja)
AR (1) AR038534A1 (ja)
AT (1) ATE368377T1 (ja)
DE (1) DE60315255D1 (ja)
TW (1) TWI301400B (ja)
WO (1) WO2003069990A2 (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070142439A1 (en) * 2000-10-23 2007-06-21 Ishihara Sangyo Kaisha Ltd. Pesticidal composition

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004028252A1 (en) * 2002-09-26 2004-04-08 Ishihara Sangyo Kaisha, Ltd. Pesticidal composition and method for controlling pest
DE102004048527A1 (de) * 2004-10-06 2006-04-13 Bayer Cropscience Gmbh Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
JP2007291020A (ja) * 2006-04-26 2007-11-08 Sumitomo Chemical Co Ltd 木材害虫用毒餌剤及び木材害虫用食餌
BRPI0721963A2 (pt) * 2007-09-18 2014-05-20 Basf Se Composição em pó, uso da composição em pó, método para controlar insetos e método para proteger material de madeira do ataque ou infestação de cupins
CN103641795B (zh) * 2013-04-18 2016-03-02 南开大学 一类含1,2,3-噻二唑的苯乙酮衍生物及其制备方法和用途
JP6189169B2 (ja) * 2013-10-16 2017-08-30 住化エンバイロメンタルサイエンス株式会社 シロアリ駆除剤の有効成分評価方法
JPWO2017104692A1 (ja) * 2015-12-15 2018-09-27 Meiji Seikaファルマ株式会社 シロアリ防除剤

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2894031A (en) * 1958-09-16 1959-07-07 Grace W R & Co Process for cyclohexanone hydrazone hydrate
US5288727A (en) * 1991-02-22 1994-02-22 Ishihara Sangyo Kaisha Ltd. Hydrazone compounds, processes for their production, intermediates useful for their production and pesticidal compositions containing them
US5360806A (en) * 1992-07-23 1994-11-01 Ishihara Sangyo Kaisha Ltd. Amide compounds and their salts and pesticidal compositions containing them
US6270784B1 (en) * 1995-08-16 2001-08-07 Bayer Aktiengesellschaft Active substance combinations comprising pyrethroids and insect development inhibitors
US7195773B2 (en) * 2000-10-23 2007-03-27 Ishihara Sangyo Kaisha, Ltd. Pesticidal composition

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US580374A (en) * 1897-04-13 cheeld
JP3355736B2 (ja) * 1993-12-20 2002-12-09 住友化学工業株式会社 殺虫、殺ダニ剤組成物
JPS5777604A (en) * 1980-11-04 1982-05-15 Ishihara Sangyo Kaisha Ltd Insecticide
JPS58189192A (ja) * 1982-04-22 1983-11-04 Nissan Chem Ind Ltd 有機リン酸エステル誘導体、その製法及びこれらを含有する有害生物防除剤
BR8303467A (pt) * 1982-06-30 1984-02-07 Union Carbide Corp Composicao inseticida sinergistica,processo para controlar insetos
JPS5980603A (ja) * 1982-10-29 1984-05-10 Nissan Chem Ind Ltd 殺虫剤組成物
JPS62111903A (ja) * 1985-11-11 1987-05-22 Nippon Kayaku Co Ltd 殺虫組成物
JPS63179808A (ja) * 1987-01-21 1988-07-23 Nippon Kayaku Co Ltd 殺虫組成物
TW282393B (ja) * 1992-06-01 1996-08-01 Dowelanco Co
JP3071962B2 (ja) * 1992-08-21 2000-07-31 石原産業株式会社 有害生物防除組成物
DE4409039A1 (de) * 1993-12-21 1995-06-22 Bayer Ag Antifouling-Mittel
DE69510333T2 (de) * 1994-02-27 1999-10-14 Rhone Poulenc Agrochimie Synergetische termitizide zusammensetzung aus pyrethroid und n-phenyl-pyrazol
DE4409040A1 (de) * 1994-03-17 1995-09-21 Bayer Ag Insektizide Wirkstoffkombinationen
RU2077199C1 (ru) * 1994-03-22 1997-04-20 Нина Александровна Алешо Пищевая токсическая приманка для синантропных тараканов
JPH10502055A (ja) * 1994-06-08 1998-02-24 ノバルティス アクチエンゲゼルシャフト 相乗作用組成物
DE19548874A1 (de) * 1995-12-27 1997-07-03 Bayer Ag Synergistische insektizide Mischungen
AU710598B2 (en) * 1996-03-29 1999-09-23 Sumitomo Chemical Company, Limited Device and method for luring termites
ATE312511T1 (de) * 1999-03-12 2005-12-15 Synergistische insektizide zusammensetzungen
MY138864A (en) * 1999-07-05 2009-08-28 Nihon Nohyaku Co Ltd Ant controllers and method for application thereof
DE10017881A1 (de) * 2000-04-11 2001-10-25 Bayer Ag Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
WO2002037964A1 (en) * 2000-11-10 2002-05-16 Syngenta Participations Ag Synergistic pesticidal compositions comprising n-cyanomethyl-4-(trifluoromethyl)nicotinamide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2894031A (en) * 1958-09-16 1959-07-07 Grace W R & Co Process for cyclohexanone hydrazone hydrate
US5288727A (en) * 1991-02-22 1994-02-22 Ishihara Sangyo Kaisha Ltd. Hydrazone compounds, processes for their production, intermediates useful for their production and pesticidal compositions containing them
US5360806A (en) * 1992-07-23 1994-11-01 Ishihara Sangyo Kaisha Ltd. Amide compounds and their salts and pesticidal compositions containing them
US6270784B1 (en) * 1995-08-16 2001-08-07 Bayer Aktiengesellschaft Active substance combinations comprising pyrethroids and insect development inhibitors
US7195773B2 (en) * 2000-10-23 2007-03-27 Ishihara Sangyo Kaisha, Ltd. Pesticidal composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070142439A1 (en) * 2000-10-23 2007-06-21 Ishihara Sangyo Kaisha Ltd. Pesticidal composition
US7514094B2 (en) 2000-10-23 2009-04-07 Ishihara Sangyo Kaisha, Ltd. Pesticidal composition

Also Published As

Publication number Publication date
TWI301400B (en) 2008-10-01
AU2003208012A1 (en) 2003-09-09
WO2003069990A2 (en) 2003-08-28
JP2004123691A (ja) 2004-04-22
EP1476017B1 (en) 2007-08-01
WO2003069990A3 (en) 2004-04-15
TW200306158A (en) 2003-11-16
ATE368377T1 (de) 2007-08-15
AR038534A1 (es) 2005-01-19
DE60315255D1 (de) 2007-09-13
JP4324391B2 (ja) 2009-09-02
US20080200522A1 (en) 2008-08-21
US7655677B2 (en) 2010-02-02
EP1476017A2 (en) 2004-11-17

Similar Documents

Publication Publication Date Title
US7655677B2 (en) Composition and method for controlling house insect pest
CA2513269C (en) Repellent
JP2866894B2 (ja) ヘキサフルムロンおよび関連化合物の殺白蟻剤としての新規な使用
RU2264099C2 (ru) Инсектицидная композиция
AU2002228956B2 (en) Termite bait composition and method
US20080033017A1 (en) Compositions for enhanced acaricidal activity
JP5674891B2 (ja) 殺虫剤組成物
TWI503077B (zh) 蠅之誘引組成物與蠅之誘引方法,以及蠅之驅除組成物與蠅之驅除方法
EA010019B1 (ru) Применение производных n-арилгидразина для борьбы с несельскохозяйственными вредителями, способ борьбы с ними, способы защиты от них и композиция приманки для их привлечения
JP4722581B2 (ja) 殺虫剤組成物
JP2003026603A (ja) コンパニオンアニマルの外部寄生虫駆除用水性滴下剤
EA014917B1 (ru) Пестицидные смеси, включающие фенилсемикарбазон
AU2003208012B2 (en) Composition and method for controlling house insect pest
JP5337831B2 (ja) 農園芸上有害な害虫の防除用組成物及び農園芸上有害な害虫の防除方法
JP4745651B2 (ja) 有害生物防除用組成物及び有害生物の防除方法
JP2000169303A (ja) シロアリ防除エアゾ―ル剤
JPH01207285A (ja) ゴキブリ誘引剤
JP4792199B2 (ja) 家屋害虫防除用組成物及び防除方法
US20100287817A1 (en) Method for Ant Control
JP2002363020A (ja) シロアリ嗜好物
WO2004030456A1 (ja) 家屋害虫防除用組成物及び防除方法
CN112998024A (zh) 一种含苯氧威的杀虫组合物及其应用
JP2003095813A (ja) 動物の外部寄生虫駆除用液剤
WO2001090075A1 (fr) Compositions combattant les ectoparasites des animaux
JP2004203834A (ja) 木材害虫防除組成物

Legal Events

Date Code Title Description
AS Assignment

Owner name: ISHIHARA SANGYO KAISHA, LTD., JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:MORITA, MASAYUKI;IMAI, OSAMU;REEL/FRAME:016569/0943

Effective date: 20040831

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION