US 20100316738A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0316738A1 UMENEZ. et al. (43) Pub. Date: Dec. 16, 2010 (54) METHODS OF INHIBITING, PREVENTING, filed on Sep. 29, 2009, provisional application No. KILLING AND/OR REPELLING INSECTS 61/247,885, filed on Oct. 1, 2009, provisional applica USING SIMULATED BLENDS OF tion No. 61/256,257, filed on Oct. 29, 2009, provi CHENOPODIUM EXTRACTS sional application No. 61/286.314, filed on Dec. 14, 2009, provisional application No. 61/329,020, filed on (76) Inventors: Desmond JIMENEZ, Woodland, Apr. 28, 2010. CA (US); Giselle Janssen, Mountain View, CA (US); Dennis (30) Foreign Application Priority Data Long, Demorest, GA (US); H. Brett Highland, Nokomis, FL Jun. 14, 2010 (US) ....................... PCT/US 10/38551 (US); Tara Lu, Woodland, CA Publication Classification (US); Gerardo Bueno, Davis, CA (US) (51) Int. Cl. AOIN 65/00 (2009.01) Correspondence Address: AOIP 7/04 (2006.01) AGRAQUEST, INC. (52) U.S. Cl. ........................................................ 424/725 1540. DREWAVENUE DAVIS, CA 95618 (US) (57) ABSTRACT The present invention provides natural and/or simulated, Syn (21) Appl. No.: 12/815,274 thetic, synergistic pesticidal compositions comprising terpe nes, such as extracts from Chenopodium ambrosioides near (22) Filed: Jun. 14, 2010 ambrosioides, or compositions based on those found in Che nopodium ambrosioides near ambrosioides. The present Related U.S. Application Data invention also provides methods of using said compositions (60) Provisional application No. 61/213,470, filed on Jun. to kill, inhibit, prevent and/or repel plant pests from contact 12, 2009, provisional application No. 61/246,872, ing and/or damaging plants. 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US 2010/03 16738A1 Dec. 16, 2010 METHODS OF INHIBITING, PREVENTING, the therapeutical effect, and Synergism exists when these KILLING AND/OR REPELLING INSECTS compounds are applied together. USING SIMULATED BLENDS OF 0006 For another example, it has been more and more CHENOPODIUM EXTRACTS accepted that synthetic crystalline vitamins differ from vita mins in natural products in many ways, since vitamins in CROSS-REFERENCE TO RELATED natural products are complexes of critical combinations and APPLICATIONS cannot be split off without destroying the biological activities, while synthetic vitamins are only synthesized fractions of a 0001. This application claims priority to U.S. Provisional Vitamin complex. Application No. 61/213,470, filed on Jun. 12, 2009, U.S. 0007 For yet another example, in Jiang, Z. et al., “Com Provisional Application No. 61/246,872, filed on Sep. 29. parative Toxicity of Essential Oils of Litsea pungens and 2009, U.S. Provisional Application No. 61/247,885, filed on Litsea cubeba and Blends of Their Major Constituents against Oct. 1, 2009, U.S. Provisional Application No. 61/256,257, the Cabbage Looper, Trichoplusia ni J. Agric. Food Chem. filed on Oct. 29, 2009, and U.S. Provisional Application No. (2009) 57, 4833-4837, the authors describe the extract of L. 61/286,314, filed on Dec. 14, 2009, and U.S. Provisional cubeba, which includes the major terpenes present in Che Application No. 61/329,020, filed on Apr. 28, 2010, each of nopodium, C-terpinene, d-limonene and p-cymene, as well as which is herein incorporated by reference in its entirety. other components. The Jiang reference notes that mortality caused by mixtures of the six known components of the TECHNICAL FIELD extract was significantly lower than that caused by the natural 0002. This invention relates to the technical field of for essential oil, Suggesting that the 10% of the unknown con mulation technology of plant protection agents and to meth stituents had a significant contribution to toxicity. Further, a combination of Y-terpinene, R-limonene and p-cymene was ods of preparing and using Such formulations. only 40% effective against Trichoplusia ni and a combination containing C-terpinene, B-pinene and C-pinene had almost no BACKGROUND mortality against T. nilarvae. 0003. The use of extracts obtained from Chenopodium 0008 Beghyn et al., Natural Compounds: Leads or Ideas? ambrosioides for controlling established insect or mite infes Bioinspired Molecules for Drug Discovery, 28 Jun. 2008, tations on plants has been described previously, including the Chemical Biology & Drug Design, 72(1): 3-15, summarize use of such extracts that include natural terpenes isolated the results of their review as follows: “In this article, we from Chenopodium. See, for example, US Published Patent compare drugs of natural origin to synthetic compounds and Application Nos. 2003/009 1657 and 2009/0030087; PCT analyze the reasons why natural compounds occupy a place of Publication Nos. WO 2001/067868 and WO 2004/006679: choice in the current pharmacopoeia.” Thus, it is well known William Quarles (1992) Botanical Pesticides from Chenopo by those skilled in the art that the synthetic analog of a natural dium, The IPM Practitioner Volume XIV, Number 2, 11 extract may have very different biological activities. This is pages; and Lorenzo Sagrero-Nieves (March/April 1995) particularly So where, as in the present invention, the extract Volatile Constituents from the Leaves of Chenopodium contains more than one active ingredient. ambrosioides L., J. Essent. Oil Res. 7:221-223, each of which 0009 US Patent Application Publication Nos. 2008/ is specifically incorporated by reference herein in its entirety. 0075796 and 2008/0020078 describe some synergistic com The prior art teaches that such extracts can be applied to binations of plant oils for controlling insects. These publica plants to kill or otherwise control certain insect species and/or tions provide long lists of essential oils, including selected mites on plants. terpenes, that may or may not be included in Such composi 0004. The prior art, however, does not appreciate that tions. These publications fail to provide specific guidance or simulated blends comprising Substantially pure terpenes can examples that would lead one of ordinary skill in the art to effectively mimic the insecticidal and acaricidal activity of arrive at the simulated, synthetic terpene compositions of the the Chenopodium plant extracts. There is a long-standing present invention or to use the simulated, synthetic terpene need to substitute natural extract from plants with active compositions of the present invention to control insects. For Substantially pure chemicals which can mimic the functions example, US Patent Application Publication No. 2008/ of the natural extract when mixed, due to limited availability 0075796 describes a composition comprising d-limonene, of plant resources, variability in plant extract compositions, C-pinene and p-cymene that is shown as being active against longer production cycle and higher cost of natural extract only farm ants. As demonstrated by the Jiang reference compared to synthetic chemicals. However, it has been described above, it is not possible to simply combine various always a challenge for researchers to identify the active ingre terpenes without testing specific combinations and amounts dients in the natural extracts from plants, and even if Such of such terpenes to arrive at insecticidally effective composi ingredients were identified, problems still remain: in some tions. cases, such ingredients cannot be synthesized through known 0010 Thus, the simulated, synthetic and synergistic pes pathways; in other cases, even if such ingredients could be ticidal compositions of the present invention are not obvious synthesized, a mere combination of them may recapitulate over the prior art, since a person with ordinary skill in the art no, or much lower, activity compared to the natural extract. will not be able to predict the necessary active ingredients to 0005 For example, despite the fact that Marinol (dronab be combined to make Such pesticidal compositions and the inol) is the only US FDA-approved synthetic cannabinoid synergistic pesticidal effects of the compositions. (chemical compound in natural cannabis), it typically pro 0011. In addition, the prior art does not appreciate that vides only limited relief to select patients, particularly when certainterpene extracts obtained from Chenopodium ambro compared to natural cannabis and its cannabinoids, since Sioides, natural analogs of Such terpenes from other plant several other cannabinoids in cannabis may also contribute to species or other organisms, and/or the synthetic versions of US 2010/03 16738A1 Dec. 16, 2010 Such terpenes can also be used in preventative or prophylactic ments, the simulated blends in the above compositions are not methods of plant protection (i.e., applied to plants before the from an extract of Chenopodium ambrosioides or from an insects and/or mites reach the economic threshold on the extract of Chenopodium.