WO 2016/038067 Al 17 March 2016 (17.03.2016) P O P C T

WO 2016/038067 Al 17 March 2016 (17.03.2016) P O P C T

(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2016/038067 Al 17 March 2016 (17.03.2016) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A01N 43/90 (2006.01) A01P 13/00 (2006.01) kind of national protection available): AE, AG, AL, AM, A01N 57/20 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, (21) Number: International Application DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, PCT/EP2015/070554 HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, (22) International Filing Date: KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, >September 2015 (09.09.2015) MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (25) Filing Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (26) Publication Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 62/048,308 10 September 2014 (10.09.2014) US kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (71) Applicant: BASF SE [DE/DE]; 67056 Ludwigshafen TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (DE). TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (72) Inventors: PAULINI, Ralph; 209 Lions Gate Drive, Cary, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, North Carolina 275 18 (US). DASCHNER, Klaus; SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, TurmstraBe 1, 67487 Maikammer (DE). GW, KM, ML, MR, NE, SN, TD, TG). (74) Agent: REITSTOTTER - KINZEBACH; Im Zollhof 1, Published: 6706 1 Ludwigshafen (DE). — with international search report (Art. 21(3)) o 00 © v o (54) Title: USE OF AFIDOPYROPENE IN GENETICALLY MODIFIED PLANTS (57) Abstract: The present invention relates to agricultural methods for controlling pests and/or increasing the plant health of cultiv ated plants having at least one modification, by treating such cultivated plants, parts of such plants, plant propagation materials or their locus of growth with afidopyropen or compositions comprising afidopyropen or mixtures of afidopyropene with another pesti - cidal active ingredient. USE OF AFIDOPYROPENE IN GENETICALLY MODIFIED PLANTS The present invention relates to a method for controlling pests and/or increasing the plant health of a cultivated plant with at least one (genetic) modification (hereinafter abbreviated as "cultivat- ed plant" and described in more details further below) as compared to the respective non- modified control plant, comprising the application of a pesticidally active pyripyropene com pound, especially afidopyropen, to a cultivated plant, parts of such plant, plant propagation ma terial, or at its locus of growth. Cultivated plants may be for example plants that have - optionally also among others - an insecticidal trait. It is a wide-spread problem that insects, that are combatted with insectides, develop resistance, i.e. they become less or not all anymore susceptible to the insecticidal effect. It has surprisingly turned out, that afidopyropene or mixtures or compositions comprising afidopyropene are useful in methods of controlling harmful insects by treating cultivated plants, parts of such plants or their locus of growth, wherein the plant has at least one trait. For exam ple methods of controlling harmful insects by treating cultivated plants, parts of such plants or their locus of growth, wherein the plant has at least one insecticidal trait and wherein the harm ful insects are resistant to an insecticidal trait of the plant. Pesticides are known to be harmful to humans and to animals in general. The environmental consequences that these pesticides cause is often complicated due to the methods of applying the pesticides by foliar spraying or direct application to the surface of the soil. Wind-drift, leaching, and runoff can cause the migration and spreading of some percentages of the pesticide out of the field of applicationdesired zone of activity. Because of such concern efforts have been made in the past to find ways to reduce the amount of chemical pesticides that are used. For example some of these efforts have focused on the development of transgenic crops that are engineered. Nevertheless, a transgenic event alone may not be sufficiently effective to protect crops from damage by pests. The total control of pest damage by any one transgenic event may even not be desirable in the long term, because of the potential for the development of resistant strains of the target pest. Alternatives to the conventional forms of pesticide application according to the present invention is the treatment of plant proparagation material, preferably seeds, with pesticides. The use of pesticides to protect seeds from attack after planting, and the use of low levels of insecticides for the protection of the crop has been used for some time. Seed treatment with pesticides has the advantages providing for the protection of the seeds, while minimizing the amount of pesticide that is required and limiting the amount of contact with the pesticide and the number of different field applications that are necessary. Therefore, although recent developments in genetic engineering of plants have improved the ability to protect plants from pests without using chemical pesticides, and while have reducing the harmful effects of pesticides on the environment, numerous problems remain that limit the successful application of these methods under actual field conditions. Accordingly, it would be useful to provide an improved method for the protection of plants, especially cultivated plants, from damage by pests. It would also be particularly useful if such method would reduce the required application rate of the pesticides, and also if it would limit the number of separate field operations that were required for crop planting and cultivation. Thus the present invention is directed to a novel method for protecting a cultivated plant against damage by one or more pests, the method comprising providing a pesticide for cultivated plant or a treated seed which seed comprises a transgenic event. Among the several advantages found to be achieved by the present invention, therefore, may be noted the provision of an improved method for the protection of cultivated plants with afidopyropen from damage by pests; the provision of such a method that would reduce the required application rate of conventional chemical pesticides; and also the provision of such a method that would limit the number of separate field operations that were required for crop planting and cultivation. Although afidopyropen and the naturally occurring insecticidal pyripyropene A derivative them selves and their combined application with other insecticides are known to have shown activity against certain crop damaging insect pests, afidopyropen and some of its selected mixtures with pesticidally active compounds (II) have not yet been described for solving discussed problems as mentioned above. The pyripyropene pesticide afidopyropen of the following formula (I), which in the following may also be referred to as "compound I", "compound of formula I" or the "compound of the present invention", is known from WO 2009/081851 (Examples, compound 4) and belongs to the class of pyripyro pene derivatives. WO 2009/081851 discloses various agrochemical formulations of afidopyropen and useful addi tives for agrochemical formulations of it. EP 1 889 540 and EP 2223599 disclose various agro- chemical formulations of pyripyropene derivatives. The Afidopyropen may be prepared by the process described in WO 2006/129714, EP 2 186 815, EP2426124, EP1 889540 and EP2426124. Further, EP 2 119 361 , WO201 1147952 and WO201 1147853 describe different mixtures of afidopyropen with other insecticidal or fungicidal active ingrdients. Pyripyropene A (pyripyropene pesticide of formula I.A herein below), produced e.g. by the method described in Journal of Society of Synthetic Organic Chemistry, Japan (1998), Vol. 56, No. 6 , pp. 478-488 or WO 94/0941 7, may for example be used as starting material for preparing further pyripyropene derivatives. (Formula I.A) Pyripyropene A has inhibitory activity against ACAT (acyl-CoA: cholesterol acyltransferase) and is expected to be applied, for example, for the treatment of diseases induced by cholesterol ac- cumulation, as described in Japanese Patent No. 2993767 (Japanese Patent Laid-Open Publi cation No. 360895/1992 ) and Journal of Antibiotics (1993), 46(7), 1168-9. Furthermore, Applied and Environmental Microbiology (1995), 6 1(12), 4429-35 describes that pyripyropene A itself has insecticidal activity against larvae of Helicoverpa zea. Furthermore, WO 2004/060065 describes that pyripyropene A has insecticidal activity against Plutella xy- lostella L larvae and Tenebrio molitor L. The subject matter of the present invention includes methods for protecting cultivated plants from attack or infestation by insects, acarids or nematodes comprising contacting the plant, or the soil or water in which the plant is growing, with afidopyropen, especially with a composition comprising afidopyropen in pesticidally effective amounts; a method for controlling insects, arachnids or nematodes comprising contacting an insect, acarid or nematode or their food sup ply, habitat, breeding grounds or their locus with afidopyropen, especially with a composition comprising afidopyropen in pesticidally effective amounts; a method for protection of plant prop agation material comprising contacting the cultivated plant propagation material, preferably seeds, with afidopyropen, especially with a composition comprising afidopyropen in pesticidally effective amounts; and finally seeds as such cultivated plant propagation material, comprising said composition.

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