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(12) United States Patent (10) Patent No.: US 7.655,677 B2 Morita Et Al

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(12) United States Patent (10) Patent No.: US 7.655,677 B2 Morita Et Al USOO7655677B2 (12) United States Patent (10) Patent No.: US 7.655,677 B2 Morita et al. (45) Date of Patent: Feb. 2, 2010 (54) COMPOSITION AND METHOD FOR (56) References Cited CONTROLLING HOUSE INSECT PEST U.S. PATENT DOCUMENTS (75) Inventors: Masayuki Morita, Shiga (JP): Osamu 5,360,806 A 11/1994 Toki et al. Imai, Shiga (JP) 5,747,519 A * 5/1998 Kodama et al. ............. 514,407 5,921,018 A * 7/1999 Hirose et al. ............... 43,132.1 (73) Assignee: Ishihara Sangyo Kaisha, Ltd., 5.990,043 A * 1 1/1999 Kugler et al. ............... 504,150 Osaka-shi (JP) 7, 195,773 B2 3/2007 Morita et al. 2007/0142439 A1 6/2007 Morita et al. (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 U.S.C. 154(b) by 38 days. FOREIGN PATENT DOCUMENTS (21) Appl. No.: 12/105,779 WO WO9324O11 A1 * 12/1993 (22) Filed: Apr. 18, 2008 (65) Prior Publication Data OTHER PUBLICATIONS US 2008/O2OO522 A1 Aug. 21, 2008 Taiwanese Office Action dated Mar. 4, 2008 (w/Partial Translation). Related U.S. Application Data * cited by examiner Primary Examiner John Pak (63) Continuation of application No. 10/504,158, filed as Assistant Examiner—Andriae M Holt application No. PCT/JP03/01711 on Feb. 18, 2003, (74) Attorney, Agent, or Firm Oblon, Spivak, McClelland, now abandoned. Maier & Neustadt, L.L.P. (30) Foreign Application Priority Data (57) ABSTRACT Feb. 22, 2002 (JP) ............................. 2002-045837 Aug. 2, 2002 (JP) ............................. 2002-226478 The present invention provides a composition for controlling a house insect pest, such as termites, ants or cockroaches, (51) Int. Cl. which comprises, as active ingredients, at least two com AOIN 43/40 (2006.01) pounds selected from the group consisting of (a) a certain AOIN 53/02 (2006.01) pyridine compound, (b) a benzoylurea compound, (c) a pyre AOIP 7/00 (2006.01) throid compound and (d) a certain hydrazone compound; and (52) U.S. Cl. ....................... 514/351; 514/341; 514/531; a composition for controlling a house insect pest, which com 514/594; 514/596 prises, as an active ingredient, a certain hydrazone com (58) Field of Classification Search ................. 514/351, pound. 514/341,531, 594,596 See application file for complete search history. 7 Claims, No Drawings US 7,655,677 B2 1. COMPOSITION AND METHOD FOR CONTROLLING HOUSE INSECT PEST (I) This application is a Continuation of U.S. application Ser. No. 10/504,158, filed on May 16, 2005, now abandoned, which was filed as a 371 of International Application PCT/ JPO3/01711, filed on Feb. 18, 2003. TECHNICAL FIELD 10 (O), The present invention relates to a composition for control wherein Y is a haloalkyl group, m is 0 or 1, and Q is ling a house insect pest, which comprises, as active ingredi ents, at least two compounds selected from the group consist 15 X RI ing of (a) a certain specific pyridine compound or its salt, (b) | / a benzoylurea compound, (c) a pyrethroid compound and (d) -C-N a certain specific hydrazone compound or its salt, particularly to a composition for controlling termites, ants or cock Ye roaches. Further, it relates also to a composition for control ling a house insect pest, which comprises, as an active ingre or a Substituted or unsubstituted heterocyclic group, (wherein dient, the above hydraZone compound or its salt. X is an oxygen atom or a sulfur atom, R' and R are respec tively independently a hydrogenatom, a Substituted or unsub stituted alkyl group, a Substituted or unsubstituted alkenyl 25 group, a Substituted or unsubstituted alkynyl group, a Substi BACKGROUND ART tuted or unsubstituted cycloalkyl group, a C(W)R group, a —OR group, a S(O)R group, a NHR' group, 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 30 S R7, U.S. Pat. No. 5,288,727 and Japanese patent 307192. As conventional agents for controlling termites, organo phosphorus compounds such as chlorpyrifos, or pyrethroids -(DN may, for example, be mentioned. Further, as agents for con 35 trolling ants, hydramethylnon, lithium sulfonate, organo a C(R)=NO R group or a substituted or unsubstituted phosphorus compounds, carbamates, or pyrethroids, may, for aryl group, or R' and R may form a =C(R')R'' group or example, be mentioned. Further, as agents for controlling may form a C-C 5-membered or 6-membered heterocyclic cockroaches, pyrethroids or organophosphorus compounds, group which may contain a nitrogenatom oran oxygenatom, may, for example, be mentioned. However, among them, 40 together with an adjacent nitrogenatom, R is a substituted or unsubstituted alkyl group, a Substituted or unsubstituted alk there are some which are feared to present toxicity against enyl group, a Substituted or unsubstituted alkynyl group, a mammals or adverse effects to environment. Under the cir Substituted or unsubstituted cycloalkyl group, a Substituted or cumstances, a new agent for controlling a house insect pest is unsubstituted aryl group, analkoxy group, an alkylthio group desired. 45 or a mono- or dialkylamino group, R is a hydrogen atom, a Substituted or unsubstituted alkyl group, a Substituted or DISCLOSURE OF THE INVENTION unsubstituted alkenyl group, a Substituted or unsubstituted alkynyl group, a Substituted or unsubstituted cycloalkyl The present inventors have conducted an extensive group, a Substituted or unsubstituted aryl group, a Substituted 50 or unsubstituted heterocyclic group ora-COR group, R is research for an agent for controlling a house insect pest. As a an alkyl group or a dialkylamino group, R is an alkyl group result, they have found specifically that by combining at least oran aryl group, Zis Nora-C R' group, R is a hydrogen two compounds selected from the group consisting of (a) atom, a halogen atom, a Substituted or unsubstituted alkyl certain specific pyridine compounds or salts thereof, (b) ben group, an alkoxy group, an alkylthio group or a nitro group. Zoylurea compounds, (c) pyrethroid compounds and (d) cer 55 Rand Rare respectively independently a hydrogenatom, a tain specific hydrazone compounds or salts thereof, as active Substituted or unsubstituted alkyl group, a Substituted or ingredients, particularly excellent effects for controlling unsubstituted alkenyl group, a Substituted or unsubstituted house insect pests can be expressed, and that certain hydra alkynyl group, a Substituted or unsubstituted aryl group or a Zone compounds or salts thereof have excellent effects for substituted or unsubstituted heterocyclic group, R'' and R' controlling house insect pests. The present invention has been 60 are respectively independently a hydrogenatom, a Substituted accomplished on the basis of this discovery. or unsubstituted alkyl group, a Substituted or unsubstituted alkenyl group, a Substituted or unsubstituted heterocyclic Namely, the present invention provides a composition for group, a N-(R')R group, a substituted or unsubstituted controlling a house insect pest, which comprises, as active alkoxy group, a Substituted or unsubstituted alkylthio group, ingredients, at least two compounds selected from the group 65 R'' and R' are respectively independently a hydrogenatom, consisting of (a) a pyridine compound of the formula (I) or its a Substituted or unsubstituted alkyl group, a Substituted or salt: unsubstituted alkenyl group, a Substituted or unsubstituted US 7,655,677 B2 3 4 alkynyl group, a Substituted or unsubstituted aryl group or a tuted with a halogen, alkyl, alkoxy, haloalkoxy, alkylthio. substituted or unsubstituted heterocyclic group, W' is an oxy phenyl (which may be further substituted with a halogen, gen atom or a Sulfur atom, and n is 1 or 2); (b) a benzoylurea alkyl, alkoxy, nitro, haloalkyl or phenoxy group), phenoxy, compound; (c) a pyrethroid compound and (d) a hydrazone phenylthio, cycloalkyl or cycloalkoxy group; a hydroxy compound of the formula (II) or its salt: group; a cyano group; a cycloalkyl group; an imino group; a —C(W)R'' group (W is an oxygen atom or a sulfur atom, R'' is a hydrogen atom; an amino group; an amino group (II) Substituted with one or two alkyl group; an alkyl group; an R5 M alkoxy group; an alkylthio group or an aryl group); a —OC N 10 (W)R group (R' is an aryl group substituted with an alkyl RSC V o orhaloalkyl group); oran alkylsulfonyl group. Also, when the :X ) is R6' y R' above Substituent is an imino group, it may form an amidino group or animidate group, together withanamino group oran / CH-V 5. alkoxy group. 15 Also, other examples of a substituent of a substituted or unsubstituted alkyl group defined as R' or R included in the wherein each of R', R and R", which are independent of Q' group in the formula (I), include a 4-haloalkyl-3-pyridin one another, is a hydrogen atom, a halogen atom, an alkyl ecarboxyamide group, a N-methyl-4-haloalkyl-3-pyridin group which may be substituted by halogen, or an alkoxy ecarboxyamide group, a 4-haloalkyl-3-pyridinecarboxya group which may be substituted by halogen, R is a halogen mide-N-alkylenoxy group, and the like. atom, an alkyl group which may be substituted by halogen, or Thus, the above compound is a dimer of a compound of the an alkoxy group which may be substituted by halogen, R is formula (I) connected by way of an alkylene chain. In the a hydrogenatom, or an alkyl group, R is X"CO (wherein same manner as above, the active ingredient of the composi X7 is a hydrogen atom, or an alkyl group), or XOCO tion for controlling a house insect pest of the present invention (wherein X is an alkyl group), or RandR" together form 25 includes a trimer.
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