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USOO8852618B2 (12) United States Patent (10) Patent No.: US 8,852,618 B2 Clough (45) Date of Patent: Oct. 7, 2014 (54) INSECTICIDAL MIXTURE CONTAINING CA 2429218 A1 6, 2002 GAMMA-CYHALOTHRN CH 689326 A5 4f1995 EP O237227 A1 9, 1987 EP 0771526 A2 5, 1997 (75) Inventor: Martin Stephen Clough, Bracknell EP O988788 A1 3f2000 (GB) FR 272O230 A1 12/1995 JP 63. 126805 A2 5, 1988 (73) Assignee: Syngenta Limited, Guildford (GB) JP 63126805 A2 5, 1988 JP 63126805 5, 1998 c - r WO WO 86 O7525 A1 12, 1986 (*) Notice: Subject to any disclaimer, the term of this WO WO 93 03618 A2 3, 1993 patent is extended or adjusted under 35 WO WO95 229O2 A1 8/1995 U.S.C. 154(b) by 824 days. WO WO9533380 A1 12, 1995 WO WO 96 16543 A2 6, 1996 (21) Appl. No.: 12/633,063 WO WO97 06687 A1 2/1997 WO WO974O692 A1 11, 1997 (22) Filed: Dec.a V88, 2009 WO WOOOO2453 A1 1, 2000 OTHER PUBLICATIONS (65) Prior Publication Data US 201O/OO81714 A1 Apr. 1, 2010 Canadian Office Action (Applin. No. 2,452,515 filed: Jul. 10, 2002) mailing date Oct. 1, 2010 (pp. 1-2). Related U.S. Application Data Allen et al. Transgenic & Conventional Insect & Weed Control Sys tems; Proceedings of the Beltwide Cotton Conference, vol. 2, 1065 (62) Division of application No. 10/484.745, filed as 1068 (1999), USA. application No. PCT/GB02/03181 on Jul. 10, 2002, Anonymous; Pesticide Mixtures for Control of Insect and Acarid now Pat. No. 7,906,127. Pests, 10, 258 (Research Disclosure 25812 (1985). Benson, et al; Economics of a Tracer/Karate Z Conventional Cotton (30) Foreign Application Priority Data Program vs. BT Cotton; Proceedings of the Beltwide Cotton Confer ence, vol. 2, 1143-1145 (1999), USA. Jul. 25, 2001 (GB) ................................... O118137.9 Bently, et al.; Fluorinated Analogues of Chrysanthemic Acid, Pestic. Sci. 11, 156-164 (1980), England. (51) Int. Cl. Boykin et al; Economics of a Karate Z/Tracer Conventional Cotton AOIN 25/02 (2006.01) Program vs. BT Cotton: Two Year Results; Proceedings of the AOIN 53/14 (2006.01) Beltwide Cotton Conference, vol. 2, 1090-1093 (2000), USA. AOIN 53/00 (2006.01) Crop Care Australasia PTY Ltd; “Karate Insecticide With Zeon Tech AOIN 25/00 (2006.01) nology’ Pamphlet (1999), Australasia. Davey, et al; Efficacy of Cyhalothrin & Lambdacyhalothrin Against (52) U.S. Cl. Boophilus microplus (Acari: Ixodidae); J. Econ. Entomol., vol. 85(6); CPC .............. A0IN 53/00 (2013.01); A0IN 25/006 2286-2290 (1992), USA. (2013.01); A0IN 25/02 (2013.01) DOW Agrosciences; "Rescue' Insecticide Label (Short Residual, USPC ................... 424/405; 424/406; 28/28: 28/89: Vapour Action Insecticide for the Knockdown of Helicoverpa spp. In 28/144; 28/229.3; 28/594 Cotton) (1999), USA. (58) Field of Classification Search Dowelanco Australia Ltd.; Details of Issue of Permit: Chlorpyrifos None Methyl / Cotton / Native Budworm, Cotton Bollworm, PER292, See application file for complete search history. KP2OW206/Version 2 (1997), Australia (including Attachment 1, pp. 1-5). (56) References Cited Elzen et al.; Evaluation of Tolerance to Insecticides in Tobacco Budworm & Bollworm Populations; Proceedings of the Beltwide U.S. PATENT DOCUMENTS Cotton Conference, vol. 2, 1289-1291 (1997), USA. Harrison, etal; Control of Lepidoptera Pests in Cotton With Intrepid 4,183,948 A 1, 1980 Huff Experimental Insecticide; Proceedings of the Beltwide Cotton Con 4,362,722 A 12, 1982 Stubbs 4,512.931 A 4, 1985 Robson ference, vol. 2, 1091-1092 (1977), USA 4,857,510 A 8, 1989 Knaufetal. 5,661,164 A 8, 1997 Otsu et al. (Continued) 6,159,991 A 12/2000 Saito 6,919,464 B1 7/2005 Crouse et al. Primary Examiner — Neil Levy 7,030,095 B2 4/2006 Janssen et al. 2002fO115565 A1 8/2002 Asrar et al. (57) ABSTRACT 2003. O108585 A1 6, 2003 Roe et al. 2004/O235959 A1 11/2004 Lahm et al. Mixtures containing gamma-cyhalothrin (S)-O-cyano-3- phenoxybenzyl (Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoro-1- FOREIGN PATENT DOCUMENTS propenyl)-2,2-dimethylcyclopropanecarboxylate and another compound having insecticidal, nematicidal, acari CA 2423995 * 4, 2002 cidal, molluscicidal, fungicidal, plant growth regulating or CA 2423995 A1 4/2002 herbicidal activity are provided. Compositions containing the CA 2424.018 4/2002 CA 2424018 A1 4/2002 mixture and insecticidal methods using Such mixtures or CA 2424.096 4/2002 compositions are also provided. CA 2424096 A1 4/2002 CA 2429218 6, 2002 4 Claims, No Drawings US 8,852,618 B2 Page 2 (56) References Cited Robson et al; 1984 British Crop Protection Conference—Pests & Diseases, vol. 3, 853-857 (1984), England. OTHER PUBLICATIONS Sparks, etal; Pyrethroid-Synergist Mixtures: Toxicity, Resistance, & Field Efficacy Toward Pyrethroid Resistant Hom Flies (Diptera: Johnson, etal; Comparison of New Insecticides for the Control of the Muscidae); Entomology Society of America, No. 0022-0493, 1567 Bollworm (Heliocoverpa zea) & Tobacco Budworm (Heliothis 1574 (1988), USA. virescens) in Arkansas; Proceedings of the Beltwide Cotton Confer Sullivan, etal; Insecticidal Efficacy AgainstaComplex of Fall & Beet ence, vol. 2,947-949 (1997), USA. Armyworms & Soybean Looper in S.C. Cotton; Proceedings of the Johnson, et al.; Evaluation of Nonsteroidal Ecdysone Agonists (Con Beltwide Cotton Conference, vol. 2, 1034-1036 (1999), USA. firm & Intrepid) for Control of Heliothine Species in Cotton; AAES Sun et al; Bibliographical Info. & Abstract, Profenofos Resistance Special Report 198, 249-254 (2000), USA. Risk in Cotton Bollworm, Helicoverpa armigera (Hubner) & The Johnson, et al; Management of the Heliothine Complex Using Tra Synergistic Mixture; Nanjing Nongye Daxue Xuebao (2000). ditional & New Insecticides; Proceedings of the Beltwide Cotton Tank; Compatibility of IWD4067 (500g/L Chlorpyrifos-Methyl EC) Conference, vol. 2, 1100-1102 (2000), USA. With Australian Cotton Insecticide Formulations; DowElanco Kerns et al; New Insecticides & Tank Mix Combinations for Worm Research Report, 1-12 (1997), Australia. Control in Lettuce; Univ. Arizona College of Agriculture Vegetable Valles etal; Temperature Effects on Cyhalothrin Toxicity in Insec Report (1999) USA. ticide-Susceptible & Resistant German Cockroaches (Dictyoptera: Kharboutli, et al; Outlook for Steward Insecticide for Control of Blattellidae); Florida Entomologist vol. 81(2), 193-201 (1988), USA. Cotton Insects, 1998-1999; Arthropod Management Tests, vol. 25. Bentley et al., Fluorinated Analogues of Chrysanthemic Acid, Pestic. 261-263 (2000), USA. Sci., 1980, 11, p. 156-164. Lance et al.; Evaluation of Insecticide Treatments for Control of Davey, R.B. et al., Efficacy of Cyhalothrin and Lambdacyhalothrin Bollworm & Tobacco Budworm on Cotton; Arthropod Management Against Boopphilus microplus (Acari: Ixodidae), Journal of Veteri Tests, vol. 25, 267-268 (1999), USA. nary Entomology, 1992, 85(6), p. 2286-2290. Micinski etal; Efficacy of selected insecticide mixtures for control of Slosser J.E. et al., "Cotton aphid response to irrigation and crop the bollworm/tobacco budworm complex. 1994; Arthropod Manage chemicals'. Southwestern Entomologist, Mar. 2001, 26(1), p. 1-14. ment Tests, Entomological Society of America, vol. 20, 207-208 Excerpt From Compendium of Pesticides Common Names; online; (1995), USA (XP000617054). Retrieved on Jan. 24, 2012. Panetal; Bibliographical Info. & Abstract, Ternary Complex Insec Tomlin, CDS., Excerpt From “The Pestocode Manual, Twelfth Edi ticide for Killing Mites & Insects, CN 1096632; Patent Application tion', British Crop Protection Council, Copyright 2000. No. CN 93-107362 (1994). Excerpt From AG ChemNew Compound Review, vol. 20, 2002. Papa, etal; Efeito DeNovo Inseticida (Avaunt 150), No Controle Da Excerpt From AG ChemNew Compound Review, vol. 19, 2001. Lagarta Rosada, Pectinophora gossypiella Bentley et al., Table titled “Isomers”, Pestic. Sc., 1980, 11, 156-64. (Lepidoptera:Gelechildae), vol. 20, 276-278 (1999), Brazil. Canadian Office Action/Request for Re-Examination to Section 48.1 Pascual, et al; Brighton Crop Protection Conference—Pests & Dis of the Patent Act for CA Patent Application No. 2452515, dated Sep. eases (3D8), 235-240 (1984), Spain. 3, 2013. Reed, et al.; Evaluation of S1812 & Pyrethroid Combinations for Schedule D Highlights of Prior Art being filed in Support of Request Management of Heliothine Larvae on Cotton, 1999; Arthropod Man for Re-Examination related to Canadian Office Action dated Sep. 3, agement Tests, vol. 25, 276 (1999), USA. 2013. Richardson, et al; XDE-225 (Gamma Cyhalothrin), A New Fully EP Decision of the Examining Division for EP Application No. 02 Resolved Pyrethroid Product D FirstYear Yield Performance; Pacific 743440.6 dated Jun. 12, 2009. Branch Entomology Society of America 85th Annual Meeting (2001), USA (One Page). * cited by examiner US 8,852,618 B2 1. 2 INSECTICDAL MIXTURE CONTAINING c) Carbamates (including aryl carbamates). Such as fenoxy GAMMA-CYHALOTHRIN carb, alanycarb, pirimicarb, triaZamate, cloethocarb, carbo furan, furathiocarb, ethiofencarb, aldicarb, thiofurox, carbo CROSS-REFERENCE TO RELATED Sulfan, bendiocarb, fenobucarb, propoXur, methomyl or APPLICATIONS oxamyl; d) Benzoyl ureas. Such as lufenuron, novaluron, noviflumu This application is a divisional of U.S. Ser. No. 10/484,745, ron, teflubenzuron, diflubenzuron, triflumuron, hexaflumu filed Oct. 22, 2004, which is a national stage of International ron, flufenoxuron or chlorfluaZuron; Application No. PCT/GB2002/03181, filed Jul. 10, 2002, e) Organic tin compounds, such as cyhexatin, fenbutatin which claims priority to United Kingdom Application No. 10 oxide or azocyclotin; 0118137.9,
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  • Transfer of Ingested Insecticides Among Cockroaches: Effects of Active Ingredient, Bait Formulation, and Assay Procedures

    Transfer of Ingested Insecticides Among Cockroaches: Effects of Active Ingredient, Bait Formulation, and Assay Procedures

    HOUSEHOLD AND STRUCTURAL INSECTS Transfer of Ingested Insecticides Among Cockroaches: Effects of Active Ingredient, Bait Formulation, and Assay Procedures 1 2 1, 3 GRZEGORZ BUCZKOWSKI, ROBERT J. KOPANIC, JR., AND COBY SCHAL J. Econ. Entomol. 94(5): 1229Ð1236(2001) ABSTRACT Foraging cockroaches ingest insecticide baits, translocate them, and can cause mor- tality in untreated cockroaches that contact the foragers or ingest their excretions. Translocation of eight ingested baits by adult male Blattella germanica (L.) was examined in relation to the type of the active ingredient, formulation, and foraging area. Ingested boric acid, chlorpyrifos, Þpronil, and hydramethylnon that were excreted by adults in small dishes killed 100% of Þrst instars within 10 d and Ͼ50% of second instars within 14 d. Residues from these ingested baits were also highly effective on nymphs in larger arenas and killed 16Ð100% of the adults. However, when the baits and dead cockroaches were removed from the large arenas and replaced with new cockroaches, only residues of the slow-acting hydramethylnon killed most of the nymphs and adults, whereas residues of fast acting insecticides (chlorpyrifos and Þpronil) killed fewer nymphs and adults. Excretions from cockroaches that ingested abamectin baits failed to cause signiÞcant mortality in cockroaches that contacted the residues. These results suggest that hydramethylnon is highly effective in these assays because cockroaches that feed on the bait have ample time to return to their shelter and defecate insecticide-laden feces. The relatively high concentration of hydramethylnon in the bait (2.15%) and its apparent stability in the digestive tract and feces probably contribute to the efÞcacy of hydra- methylnon.
  • Onion Production, Maggot Control, and Cyromazine

    Onion Production, Maggot Control, and Cyromazine

    Onion Production, Maggot Control, and Cyromazine Cyromazine (Trigard®) is currently undergoing re-evaluation at EPA/OPP. The Preliminary Risk Assessment conducted by the Environmental Fate & Effects Division of OPP indicates a high risk to birds from onion seed treatment with cyromazine. BEAD needs assistance to better characterize the use of cyromazine in commercial bulb onion production. From the Old Crop Profiles: cyromazine is used on onion seed to control onion maggots and/or seed corn maggots. Is this still correct? Cyromazine is not widely used as a seed treatment for onion seed planted in the western US. 1. Since this is a seed treatment, what percentage of commercial onion growers (or how many acres) is planting seed? How many growers (or acres) plant seedlings? At least 90% of US dry bulb storage onion acreage is seeded. In Washington State in 2013, 20,500 acres were seeded and only approximately 500 acres transplanted. In California, nearly all dehydrator onions are seeded. 2. Are there data to indicate how many acres are using cyromazine seed treatment and how many acres are using the alternative treatments each year? The California Pesticide Use Report for 2011 contains 12 records (see attached) of onion seed treatment with cyromazine (Trigard OMC) for a total of 474.3 lbs active ingredient. It is not known if the seed treated in California was planted in California or the western states. In addition, if seed planted in California were treated out-of-state it would not appear in the database. Regarding cyromazine seed treatment on onions, David Belles from Syngenta Crop Protection stated, “It is treated on onion for export to Canada because we don’t have Regard labeled in Canada.