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(12) United States Patent (10) Patent No.: US 8,709,976 B2 Tam (45) Date of Patent: Apr

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(12) United States Patent (10) Patent No.: US 8,709,976 B2 Tam (45) Date of Patent: Apr US0087.09976B2 (12) United States Patent (10) Patent No.: US 8,709,976 B2 Tam (45) Date of Patent: Apr. 29, 2014 (54) ANTHRANILIC DIAMIDE COMPOSITIONS WO 2009/002856 12/2008 FOR PROPAGLE COATING WO WO-2009002856 * 12/2008 WO WO 2011049233 * 4, 2011 (75) Inventor: Wilson Tam, Boothwyn, PA (US) OTHER PUBLICATIONS (73) Assignee: E I du Pont de Nemours and MSDS BRIJ 78, 2005.* Company, Wilmington, DE (US) Adjuvant Compositions, 20110082037, 2011.* U.S. Appl. No. 13/234,174. Nonfinal Office Action, Dated Jun. 1, 2012. *) Notice: Subject to anyy disclaimer, the term of this U.S. Appl. No. 13/234,171, Dated May 24, 2012. patent is extended or adjusted under 35 U.S. Appl. No. 13/234,177, Dated May 24, 2012. U.S.C. 154(b) by 0 days. U.S. Appl. No. 13/234,179, Dated May 24, 2012. Tetsumi et al. Amorphous Water-Soluble Cyclodextrin (21) Appl. No.: 13/234,176 Derivatives . , Pharmaceutical Research, vol. 5., No. 11, 1988. Ben et al., Application of NMR for the Determination of HLBValues (22) Filed: Sep. 16, 2011 of Nonionic Surfactants, Journal of the American Oil Chemists’ Society, 1972, Vol. 49(8), pp. 499-500. (65) Prior Publication Data Guo et al., Calculation of Hydrophile-Lipophile Balance for Polyethoxylated Surfactants by Group Contribution Method, Journal US 2012/O149565A1 Jun. 14, 2012 of Colloid and Interface Science, 2006, 298, pp. 441-450. Pitha et al. Amorphous Water-Soluble Derivatives of Cyclodextrins: Nontoxic Dissolution Enhancing Excipients, 1985, vol. 74 (9), pp. Related U.S. Application Data 987-990. (60) Provisional application No. 61/422,257, filed on Dec. Trapani et al., Determination of Hydrophile-Lipophile Balance of Some Polyethoxylated Non-Ionic Surfactants by Reversed-Phase 13, 2010. Thin Layer Chromatography, International Journal of Pharmaceutics, 1995, vol. 116, pp. 95-99. (51) Int. Cl. Berger et al., Apparent and Real Distribution in GPC, Separation AOIN 25/26 (2006.01) Science, 1971, 6(2), pp. 297-303. A6 IK3I/44 (2006.01) Griffin, Classification of Surface-Active Agents by HLB, J. Soc (52) U.S. Cl. Cosmet, 1949. 1, pp. 311-326. USPC ........................................... 504/100; 514/341 Nelson et al., Small-Angle Neutron Scattering Study of Adsorbed (58) Field of Classification Search Pluronic Tri-Block Copolymers on Laponite, Langmuir, 2005, Vol. None 21, pp. 91.76-9182. See application file for complete search history. * cited by examiner (56) References Cited Primary Examiner — Alton Pryor U.S. PATENT DOCUMENTS (57) ABSTRACT 5,527,760 A 6/1996 Rensing et al. 5,710,268 A 1/1998 Wimmer Disclosed is an insecticidal composition comprising by 6,202,345 B1 3, 2001 Wokal weight based on the total weight of the composition: 6,747,047 B2 6, 2004 Lahm et al. (a) from about 9 to about 91% of one or more anthranilic 7,247,647 B2 7/2007 Hughes et al. diamide insecticides; and 7,696.232 B2 * 4/2010 Berger et al. ................. 514,341 2012fO149563 A1 6, 2012 Tam et al. (b) from about 9 to about 91% of a nonionic fatty alcohol 2012fO149564 A1 6, 2012 Tam ethoxylate component having a water Solubility of at 2012fO149566 A1 6, 2012 Holowka least about 5% by weight at 20°C., a hydrophilic-lipo 2012/O1495.67 A1 6, 2012 Holowka philic balance value of at least about 5, and an average molecular weight ranging from about 300 to about FOREIGN PATENT DOCUMENTS 10,000 daltons; wherein the ratio of component (b) to component (a) is CN 10 15541.69 * 10/2009 CN 1016O7940 12/2009 about 1:10 to about 10:1 by weight. WO O3,O15519 2, 2003 Also disclosed is a geotropic propagule coated with an insec WO 2003/O15518 2, 2003 ticidally effective amount of the aforedescribed composition. WO WO-O3O15518 * 2/2003 Further disclosed is a liquid composition comprising the WO O3,024222 3, 2003 WO WO-03024222 * 3/2003 insecticidal composition, and a method for protecting a geo WO 2004/O27042 1, 2004 tropic propagule and plant derived therefrom from a phy WO 2004067528 8, 2004 tophagous insect pest. WO 2006/062978 6, 2006 WO 2008/0699.90 6, 2008 14 Claims, No Drawings US 8,709,976 B2 1. 2 ANTHRANILC DAMIDE COMPOSITIONS (b) from about 9 to about 91% of a nonionic fatty alcohol FOR PROPAGLE COATING ethoxylate component having a water Solubility of at least about 5% by weight at 20°C., a hydrophilic-lipo CROSS-REFERENCE TO RELATED philic balance value of at least about 5, and an average APPLICATIONS molecular weight ranging from about 300 to about 10,000 daltons; wherein the ratio of component (b) to component (a) is This application claims the benefit of the U.S. Provisional about 1:10 to about 10:1 by weight. Application No. 61/422,257, filed on Dec. 13, 2010. Another aspect of the present invention is a geotropic propagule coated with an insecticidally effective amount of FIELD OF THE INVENTION 10 the aforedescribed insecticidal composition. Another aspect of the present invention is a liquid compo This invention relates to compositions comprising anthra sition consisting of about 5 to 80 weight % of the afore nilic diamide insecticides and nonionic fatty alcohol ethoxy described insecticidal composition and about 20 to 95 weight lates. This invention also relates to geotropic propagules % of a Volatile aqueous liquid carrier. coated with these compositions and to protecting propagules 15 Another aspect of the present invention is a method for and derived plants from phytophagous insect pests by con protecting a geotropic propagule and plant derived therefrom tacting the propagules with these compositions. from a phytophagous insect pest, the method comprising coating the propagule with an insecticidally effective amount BACKGROUND of the aforedescribed liquid composition and then evaporat ing the Volatile aqueous liquid carrier of the composition. Damage by phytophagous insect pests to geotropic propagules Such as seeds, rhizomes, tubers, bulbs or corms, DETAILED DESCRIPTION and plants derived therefrom causes significant economic As used herein, the terms “comprises.” “comprising.” losses. “includes.” “including.” “has.” “having.” “contains.” “con Anthranilic diamides, alternatively called anthranilamides, 25 taining.”“characterized by or any other variation thereof, are are a recently discovered class of insecticides having activity intended to cover a non-exclusive inclusion, Subject to any against numerous insect pests of economic importance. PCT limitation explicitly indicated. For example, a composition, Publication WO 03/024222 discloses treatment with anthra mixture, process or method that comprises a list of elements nilic diamides being useful for protecting propagules from is not necessarily limited to only those elements but may phytophagous invertebratepests. Furthermore, because of the 30 include other elements not expressly listed or inherent to such ability of anthranilic diamides to translocate within plants, composition, mixture, process or method. not only the propagules, but also new growth developing from The transitional phrase “consisting of excludes any ele the propagules can be protected. ment, step, or ingredient not specified. If in the claim, Such Although anthranilic diamides have properties making would close the claim to the inclusion of materials other than them Suitable for protecting propagules and developing 35 those recited except for impurities ordinarily associated growth, achieving Sufficient absorption of anthranilic dia therewith. When the phrase “consisting of appears in a mides into the propagule and developing roots to cause insec clause of the body of a claim, rather than immediately fol ticidally effective concentrations in parts of the developing lowing the preamble, it limits only the element set forth in that plant for which protection is desired can be problematic. clause; other elements are not excluded from the claim as a Although anthranilic diamide coatings on propagules are whole. exposed to moisture from the propagules and Surrounding 40 The transitional phrase “consisting essentially of is used plant growing medium (e.g., Soil), the low water solubility of to define a composition, or method that includes materials, anthranilic diamide insecticides impedes their mobilization steps, features, components, or elements, in addition to those through moisture. Also, until the anthranilic diamides are literally disclosed, provided that these additional materials, absorbed into the propagules and developing roots, they are steps, features, components, or elements do not materially Vulnerable to absorption and dissipation through the growing 45 affect the basic and novel characteristic(s) of the claimed medium. invention. The term “consisting essentially of occupies a Achieving insecticidally effective concentrations of middle ground between "comprising and “consisting of anthranilic diamides in foliage by treating propagules Where applicants have defined an invention or a portion requires greater amounts of anthranilic diamides to be avail thereof with an open-ended term Such as “comprising it able for transport greater distances within the plant. Because 50 should be readily understood that (unless otherwise stated) the rapidly expanding Volume of plant tissue in growing foli the description should be interpreted to also describe such an age inherently dilutes anthranilic diamide concentrations, invention using the terms “consisting essentially of or “con absorption of increased amounts of anthranilic diamides is sisting of required for protection of foliage, particularly if protection of Further, unless expressly stated to the contrary, “or refers foliage beyond the first couple leaves and during a substantial 55 to an inclusive or and not to an exclusive or. For example, a part of the growing season is desired. condition A or B is satisfied by any one of the following: A is Accordingly, need exists for new compositions promoting true (or present) and B is false (or not present), A is false (or the absorption of anthranilic diamide insecticides into not present) and B is true (or present), or both A and B are true propagules and developing roots.
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