(12) United States Patent (10) Patent No.: US 6,583,088 B1 Andersch (45) Date of Patent: Jun
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USOO6583088B1 (12) United States Patent (10) Patent No.: US 6,583,088 B1 Andersch (45) Date of Patent: Jun. 24, 2003 (54) USE OF SPINOSYNES AS SOIL (58) Field of Search ......................... 514/450; 424/405; INSECTICDES 504/140, 209 (75) Inventor: Wolfram Andersch, Bergisch Gladbach (56) References Cited DE (DE) U.S. PATENT DOCUMENTS (73) Assignees: Bayer Aktiengesellschaft, Leverkusen 5,362,634 A 11/1994 Boeck et al. ................. 435/76 (DE); Dow Agrosciences LLC, 5,670,364 A 9/1997 Mynderse et al. ....... 435/252.1 Indianapolis, IN (US) 5,670,486 A 9/1997 Mynderse et al. ............ 514/28 5,840,861 A 11/1998 Mynderse et al. ......... 536/16.8 (*) Notice: Subject to any disclaimer, the term of this 6,001,981. A * 12/1999 DeAmicis et al. ........... 536/7.1 patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. OTHER PUBLICATIONS (21) Appl. No.: 09/700,674 Dow Elanco Trade Magazine, Down to Earth, vol. 52, No. 1 (month unavailable), 1997, pp. 1-24, G. D. Thompson et (22) PCT Filed: May 14, 1999 al, “The Discovery of Saccharopolyspora Spinosa and a (86) PCT No.: PCT/EP99/03318 New Class of Insect Control Produces”. S371 (c)(1), * cited by examiner (2), (4) Date: Nov. 17, 2000 Primary Examiner Alton Pryor (87) PCT Pub. No.: WO99/60856 (74) Attorney, Agent, or Firm Joseph C. Gil; John E. Mrozinski, Jr.; Richard E. L. Henderson PCT Pub. Date: Dec. 2, 1999 (57) ABSTRACT (30) Foreign Application Priority Data The present invention relates to the use of Spinosyns for May 26, 1998 (DE) ......................................... 198 23397 treating Seed and plant propagation material. (51) Int. Cl." ................ ... A01N 43/02; AO1N 43/00 (52) U.S. Cl. ........................................ 504/140; 504/209 3 Claims, No Drawings US 6,583,088 B1 1 2 USE OF SPINOSYNES AS SOL It has now been found that Spinosyns have Systemic INSECTICDES properties and that application via the Soil or via plant irrigation is possible. They may also be used for treating This Application is a 371 of PCT/EP99/03318 filed May Seed and plant propagation material. 14, 1999. The present invention relates to the use of Spinosyns, in particular for treating the Soil, for treating Seed or plant The Spinosyns are known compounds. The fermentation propagation material, and for drenching and irrigating product described in U.S. Pat. No. 5,362,634 (A83543) is plants. composed of a variety of compounds termed Spinosyn A, B, It is known that Spinosyns can be used for controlling 10 C and the like (cf. WO97/00 265, WO 93/09 126 and WO insects (WO 9700265, WO 93/09 126, WO 94/20518, U.S. 94/20518). The spinosyns may be represented by the Pat. No. 5,362,634). following formulae (I) and (II): (I) OR6 Compound Spinosyn A CH (CH3)2N NLVCH CHS CH, CH, CH Spinosyn B CH, (CH3)2NH NbCH CH, CH, CH, CH Spinosyn C CH, HN Y!'CH CH, CH, CH, CH Spinosyn D CH, CH, (CH3)2NYl CH CHS CH, CH, CH Spinosyn E CH (CH3)2NY CH - CH, CH, CH, CH, Spinosyn F H CH CHS CH, CH, CH Spinosyn G CHs (CH)N CH, CH, CH, CH CH Spinosyn H C H C C CH Y CbyH3 2 Hs H H US 6,583,088 B1 -continued (I) R1 Compound Spinosyn J CH CH CHs CH CH Spinosyn K CH, CHs CH, CH, Spinosyn L. CH CH CC CHs CH CH Spinosyn M C CH CH3HH 3OOO 2 Hs CH CH N-V Spinosyn N CH CH C 2 Hs CH CH O Spinosyn O CH CH C 2 Hs CH CH Spinosyn P CH C 2 Hs CH Spinosyn Q C CH CH CCC 2 Hs CH CH Spinosyn R C CH, CHHHH333 3OOO 2 Hs CH, CH, NV Spinosyn S CH CH CH CH Spinosyn T C CH OO 2 Hs CH Spinosyn U C CH CCCH3HH3 2 Hs CH Y by US 6,583,088 B1 -continued (I) Compound R4 Spinosyn V CH CH Y CH - CHs CH Spinosyn W CH, CH, Y CHby CHs CH, Spinosyn Y CH Y CHby CHs CH CH Spinosyn A 17-Psa CH CHs CH CH CH Spinosyn D 17-Psa CH, CHs CH, CH, CH, Spinosyn E 17-Psa CH CHs CH CH CH Spinosyn F 17-Psa CHs CH CH CH Spinosyn H 17-Psa CH CHs C CH Spinosyn J 17-Psa CH, CHs CH, CH, Spinosyn L. 17-Psa CH CHs CH " CH and (II) Compound Spinosyn A 9-Psa Spinosyn D 9-Psa CH CH US 6,583,088 B1 -continued (II) Compound R1 R2 R3' R4 Rs' Spinosyn A aglycone H CH H CHs H Spinosyn Daglycone CH CH H CHs H There have also been disclosed Semisynthetic Spinosyns R” represents methyl or ethyl. of the formula (Ia) The term "spinosyn” as used herein encompasses the compounds disclosed in WO97/00265. (Ia) Individual Spinosyns, but also mixtures of the abovemen tioned spinosyns of the formulae (I), (Ia) and (II) may be used according to the invention. Mixtures comprising at least one Spinosyn of the formula QRCH, OR! (I) or (II) are preferably used. O OR3 Mixtures comprising a mixture of Spinosyn A and Spino syn D in which the ratio of spinosin A to spinosyn D is generally between approximately 80:20 and approximately 98:2, a value of approximately 85:15 being preferred, are preferably used. Spinosad (see, for example, Dowlanco 35 trade magazine Down to Earth, Vol. 52, No. 1, 1997 and the literature cited therein), which comprises essentially a mix ture of Spinosyn A and Spinosyn D in a ratio of approxi mately 85:15, is especially preferably used. In particular, the fermentation product A 83543, which (WO 97/00 265) in which 40 comprises approximately 85 to 90% of Spinosyn A, approxi A and B each represent a single bond, a double bond or mately 10 to 15% of spinosyn D and minor amounts of an epoxide unit, spinosyns B, C, E, F, G, H and J and which is disclosed in R represents U.S. Pat. No. 5,362,634, is used. The acid addition salts described therein may also be 45 used. N or R8-O, The following types of Seed and plant propagation mate M rial are preferably treated according to the invention: R8 Maize, cereals (Such as, for example, wheat, barley, oats, rye), rice, Seed potatoes, cotton, oilseed rape, Sunflower, beet R" represents hydrogen or methyl, (Such as, for example, Sugar beet), vegetable Seed (Such as, R, R and R' independently of one another represent 50 for example, onion, cabbage, tomato), (fodder) legumes, C-C -alkyl, C-C-haloge no alkyl, C-C- peanuts, Soya, Sorghum. alkylcarbonyl or protected hydroxyl, The following general treatment methods are preferably R represents hydrogen, C-C-alkyl, C-C-alkylamino Suitable for carrying out the Seed treatment, or plant propa or represents alkylhydroxylamino of the formula 55 gation material treatment, according to the invention: dry treatments (preferably with addition of adhesion pro -N-OR11 moters Such as, for example, liquid paraffin or talc), and, if appropriate, colorants, OR10 slurry treatments (preferably with addition of wetters, 60 dispersants, emulsifiers, adhesives, inert fillers and in which colorants), R" and R' independently of one another represent aqueous liquid treatments (preferably with addition of hydrogen, C-C-alkyl or C-C-alkylcarbonyl, emulsifiers, dispersants, thickeners, antifreeze agents, R represents hydrogen or methyl, polymers, adhesives and colorants), R", R and R independently of one another represent 65 solvent-based liquid treatments (with addition of solvents C-C-alkyl, C-C-halogenoalkyl or C-C- and colorants), emulsion treatments (with addition of alkylcarbonyl, or represent protected amino, and emulsifiers, Solvents and colorants). US 6,583,088 B1 9 10 The total active compound content in the Spinosyn treat LO cust a migratoria migrat Orioides, Melanoplus ment formulations preferably amounts to 10 to 80% by differentialis, Schistocerca gregaria. weight. From the order of the Dermaptera, for example, Forficula Preferably, 1 to 300 g of active compound are applied to auricularia. every 100 kg of Seed or plant propagation material in the From the order of the Isoptera, for example, Reticuliter form of a treatment. meS Spp. From the order of the Anoplura, for example, Phylloxera The treatment method according to the invention is car vaStatrix, Pemphigus spp., Pediculus humanus CorpOris, ried out in customary treatment apparatuses or drum mixers Haematopinus spp., Linognathus spp. as are customary, for example, in the construction industry. From the order of the Mallophaga, for example, Tri Seed (or plant propagation material) and Seed treatment chodectes spp., Damalinea spp. formulation (or treatment formulation for plant propagation From the order of the Thysanoptera, for example, Fran material) are mixed intimately in a conventionally used kliniella Occidentalis, Hercinothrips femoralis, Thrips treatment apparatus. palmi, Thrips tabaci. After the Seed (or plant propagation material) has been From the order of the Heteroptera, for example, Euryga treated, it is dried to a Sufficient degree in the case of the wet 15 Ster spp., Dysdercus intermedius, Piesma quadrata, Cimex treatments, and the resulting treated Seed (or plant propaga lectularius, Rhodnius prolixus, Triatoma spp. tion material) is then packaged in portions. From the order of the Homoptera, for example, Aleurodes When applying the Seed or plant propagation material brassicae, Bemisia tabaci, Trialeurodes vaporariorum, which has been treated according to the invention, 1 to 5000 Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, kg of treated Seed (or plant propagation material) are gen Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hya erally employed per hectare of area under cultivation, pref lopterus arundinis, MacroSiphum avenae, Myzus spp., erably 100 to 300 kg of seed (or plant propagation material) Phorodon humuli, RhopaloSiphum padi, Empoasca spp., per hectare of area under cultivation.