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(12) United States Patent (10) Patent No.: US 8,137,715 B2 Shah Et Al

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(12) United States Patent (10) Patent No.: US 8,137,715 B2 Shah Et Al US008137715B2 (12) United States Patent (10) Patent No.: US 8,137,715 B2 Shah et al. (45) Date of Patent: Mar. 20, 2012 (54) INSECTICIDAL COMPOSITION WO 02089584 A1 11, 2002 WO 2006055O29 A1 5, 2006 (75) Inventors: Sujay Anil Shah, London (GB); WO 2006066152200606451 1 A1A2 6, 2006 Christopher William Horsler, WO 2008O11054 A2 1, 2008 Southampton (GB) WO 2008O15413 A2 2/2008 WO 2008O35O29 A2 3, 2008 (73) Assignee: Livie Biopesticides Limited, London (GB) OTHER PUBLICATIONS DWACC 2006-522510, Jul. 2006, Derwent and WO2, Linder et al.* *) Notice: Subject to anyy disclaimer, the term of this Ahmed, S. et al., "Stabilization of Pyrethrins for Prolonged Residual patent is extended or adjusted under 35 Toxicity”, “Pyrethrum Post”, 1976, pp. 82-88, vol. 13, No. 3. U.S.C. 154(b) by 339 days. Bestmann, H. et al., (Abstract Only), “Plant Insecticides. III. Pyrethrin I in the essential oil of Chrysanthemum balsamita L'. (21) Appl. No.: 12/375,533 "Zeitschrift fur Naturforschung. C. A journal of biosciences”, 1986, pp. 725-728, vol. 41, No. 7-8; Published in German. (22) PCT Filed: Jul. 30, 2007 Dong, Y. et al., (Abstract Only), “Analysis of chemical components in volatile oils from Rhizoma Chuanxiong by GS-MS”, “Shizhen (86). PCT No.: PCT/GB2OOTFOO2881 Guoyi Guoyao Bianweihui”, 2006, p. 555, vol. 17. No. 4. Handa, S. et al., (Abstract Only), "Evaluation of dill apiole and S371 (c)(1), dihydrodilapiole as Synergists for pyrethrins in dust formulations'. (2), (4) Date: Mar. 10, 2009 “Pyrethrum Post”, 1975, pp. 45-46, vol. 13, No. 2. Kumar, A. et al., “Secondary metabolites of Chyrsanthemum genus (87) PCT Pub. No.: WO2008/035029 and their biological activities”, Nov. 10, 2005, pp. 1489-1501, vol. 89, No. 9. PCT Pub. Date: Mar. 27, 2008 Lichtenstein, P. et al., (Abstract Only), "Insecticidal and Synergistic components isolated from dill plants”, “Journal of Agriculture and (65) Prior Publication Data Food Chemistry”, 1974, pp. 658-664, vol. 22, No. 4. Meheshwari, M. et al., “Novel Methylenedioxyphenyl Synergists for US 2009/0263511 A1 Oct. 22, 2009 Pyrethrum and Carbamate Insecticides From Dillapiole”, “Indian Perfumer, 1978, pp. 155-160, vol. 22, No. 3. (30) Foreign Application Priority Data Reddy, M. et al., "Characterization and Use of Essential Oils From Thymus vulgaris Against Botrytis cinerea and Rhizopus stolonifer in Aug. 3, 2006 (GB) ................................... O615475.1 Strawberry Fruit”, “Phytochemistry”, 1998, pp. 1515-1520, vol. 47, Feb. 15, 2007 (GB) ................................... O702915.0 No. 8. Bylaite, Egle, et al., “Composition of Essential Oil of Costmary (51) Int. Cl. Balsamita major (L.) Desf, at Different Growth Phases”. “J. Agric. A6 IK36/00 (2006.01) Food Chem”, 2000, pp. 2409-2414, vol. 48. Janmaat, Alida F., et al., “Enhanced fumigant toxicity of p-cymene (52) U.S. Cl. ....................................................... 424f776 against Frankliniella Occidentalis by simultaneous application of (58) Field of Classification Search ........................ None elevated ...”. “Pest Management Science”, 2001, pp. 167-173, vol. See application file for complete search history. 58. Juven, B.J., et al., “Factors that interact with the antibacterial action (56) References Cited ofthyme essential oil and its active constituents”, “Journal of Applied Bacteriology”, 1994, pp. 626-631, vol. 76. U.S. PATENT DOCUMENTS Regnault-Roger, Catherine, et al., “Fumigant toxic activity and repro 5,645,845. A 7, 1997 Neumann et al. ductive inhibition induced by monoterpenes on Acanthoscelides 6.296,865 B1 10/2001 Dujardin et al. obtectus (Say)...”. “Journal of Stored Products Research'', 1995, pp. 6,835,719 B2 * 12/2004 Parker et al. .................... 514,65 291-299, vol. 31, No. 4. 6,849,614 B1 2/2005 Bessette et al. Tunaz, H., et al., “Insect Growth Regulators for Insect Pest Control”. 2002/0022043 A1 2, 2002 Miller “TurkJ Agric For”, 2004, pp. 377-387, vol. 28. 2005/0038094 A1* 2/2005 Warrington ................... 514,383 2005/0244445 A1 11/2005 Anderson * cited by examiner FOREIGN PATENT DOCUMENTS Primary Examiner — Christopher R Tate CN 1647644 A 8, 2005 Assistant Examiner — Randall Winston CN 1647645 A 8, 2005 CN 1792.154 A 6, 2006 (74) Attorney, Agent, or Firm — Hultquist, PLLC; Steven J. CN 1806550 A T 2006 Hultquist; Kelly K. Reynolds DE 3717467 A1 12/1988 DE 3733640 A1 4f1989 (57) ABSTRACT DE 19824681 A1 12/1999 EP 1634500 A2 3, 2006 The use of dill oil or a mixture of two or more components FR 2O71322 A 9, 1971 thereof as a potentiator for a pesticide. Such as an insecticide IN 188378 A1 9, 2002 and in particular a pyrethroid is described, together with JP 62-114904 A 5, 1987 JP 2006257.050 A1 9, 2006 compositions containing dill oil, and their use in agriculture WO 96.39034 A1 12, 1996 and in Veterinary applications. WO 0005964 A1 2, 2000 WO O16O163 A2 8, 2001 14 Claims, 6 Drawing Sheets U.S. Patent Mar. 20, 2012 Sheet 1 of 6 US 8,137,715 B2 Figure 1 () 2 foL s t O h CU O E C C s () d 400 600 800 Rate g product/ha Figure 2 - - -0-preCOunt -8-96hr AA 400 600 Rate g productha U.S. Patent Mar. 20, 2012 Sheet 2 of 6 US 8,137,715 B2 Figure 3 O 200 400 600 800 1000 Rate g product/ha Figure 4 -0-precount 120 ...B. 96hr AA Rate g product/ha U.S. Patent Mar. 20, 2012 Sheet 3 of 6 US 8,137,715 B2 Figure 5 9. C OL s O 9 O E C s (9 s 6OO Rate g product/ha Figure 6 5 100 s 9 80 w == 60 8 / ta N1 20 Ya-...--ir-" " 8" -...-...-. -sea al-... O s' reas.... '.. O 2OO 400 600 800 1 OOO Rate g product/ha U.S. Patent Mar. 20, 2012 Sheet 4 of 6 US 8,137,715 B2 Figure 7 45 40 3. 35 e 30 t is 25 3 20 E E 2 15 9 as 10 e tail, OO5 eve 5f significance v w i Ratio of pyrethrin:dill seed oil Figure 8 % Control of Bemisia tabaci on peppers after application of pyrethrin formulations E1DAA E4DAA o7DAA to 14DAA 48.5 24.2 12.1 6.06 3.03 Std (4.8) Rate of pyrethrin applied (g/ha) U.S. Patent Mar. 20, 2012 Sheet 5 of 6 US 8,137,715 B2 Figure 9 % Control of Bennisia tabaci on tomatoes after application of pyrethrin formulations 100 48.5 24.2 12.1 6.06 3.03 Std (4.8) Rate of pyrethrin applied (g/ha) Figure 10 % Control of Bemisia tabaci "larvae' four days after application (4DAA) of pyrethrin formulations 80 60 Peppers 40 Tomatoes Rate of pyrethrin applied (g/ha) U.S. Patent Mar. 20, 2012 Sheet 6 of 6 US 8,137,715 B2 Figure 11 % Control of Bemisia tabaci "larvae' seven days after application (7DAA) of pyrethrin formulations 1 O O 8 O Peppers 264.OO O it is Tomatoes O 48.5 24.2 12.1 6.06 3.03 Std (4.8) Rate of pyrethrin applied (g/ha) Figure 12 % Control of Bemisia tabaci "larvae' fourteen days after application (14DAA) of pyrethrin formulations 100 . V Peppers Tomatoes O O S Rate of pyrethrin applied (glha) US 8,137,715 B2 1. 2 INSECTICDAL COMPOSITION following rapid knockdown, and has low mammalian toxic ity, low residual activity, low cost, no existing resistance in CROSS-REFERENCE TO RELATED target pest species and the low possibility of future resistance APPLICATIONS developing. It would also be desirable to provide a new potentiator for This application is a U.S. national phase under the provi pesticides and in particular pyrethrin insecticides which is sions of 35 USC S371 of International Application No. PCT/ safe and effective to use. GB07/02881 filed Jul.30, 2007, which in turn claims priority Dill, Anethum graveolens L., an annual or biennial herb of Great Britain Patent Application No. 0615475.1 filed Aug. native to Europe and South-western Asia, is naturalized to 3, 2006, and Great Britain Patent Application No. 0702915.0 10 North America and the West Indies. Also known as common filed Feb. 15, 2007. The disclosures of such international dill, American dill, European dill and Danish dill. Principal application and Great Britain priority applications are hereby dill production areas are India and Pakistan but Egypt, Fiji, incorporated herein by reference in their respective entireties, Mexico, the Netherlands, the United States of America, for all purposes. England, Hungary, Germany and Holland also have commer The present invention relates to the use of dill oil, or com 15 cially productive areas. The plant grows erect and can reach a binations of components or fractions thereofas a potentiator height of one meter. It is characterised by hollow stems, for insecticides, in particular for pyrethrin insecticides, as blue-green leaves, and yellow-flowering compound umbels, well as to pesticidal compositions comprising dill oil and which produce a dried ripe fruit commonly called seeds. methods of using them. The essential oils of dill differin flavour and odour depend Pyrethrum is a highly effective pesticide which has been ing upon whether they are obtained from mature seed or dill used for centuries against all manner of insect pests. Pyre weed. The seed oil resembles the essential oil of caraway thrum is a natural plant oil that is present in the pyrethrum because of the high carvone content (reaching 50 to 60 per daisy, Chrysanthemum (Tanacetum cineraria efolium), a cent) in mature seeds. Dill seed oil includes d-carvone, d-li member of the chrysanthemum family. It is found mainly in monene, d-phellandrene, C-pinene, diterpene, d-dihydrocar tiny oil containing glands on the Surface of the seed case in the 25 vone, C.-phellandrene, B-pinene, 1,8-cineole, B-myrcene, tightly packed flower head and is the plants own insecticide para-cymene, thujone (C-thujone and B-thujone) and dilapi that it has evolved to keep insects away.
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