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(12) United States Patent (10) Patent N0.: US 7,960,354 B2 Huang Et Al

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(12) United States Patent (10) Patent N0.: US 7,960,354 B2 Huang Et Al US007960354B2 (12) United States Patent (10) Patent N0.: US 7,960,354 B2 Huang et al. (45) Date of Patent: *Jun. 14, 2011 (54) SYNERGISTIC PESTICIDAL MIXTURES (56) References Cited (75) Inventors: Jim X. Huang, Carmel, IN (US); U.S. PATENT DOCUMENTS Jonathan M. Babcock, Carmel, IN 7,511,149 B2 3/2009 Arndt et al. (US); Thomas Meade, Zionsville, IN 7,705,154 B2 4/2010 Heller et a1. (US); Marc Farrow, Fishers, IN (US) 7,705,156 B2 4/2010 Loso et al. 7,709,648 B2 5/2010 Meyer et a1. Assignee: DoW AgroSciences LLC, Indianapolis, 7,709,649 B2 5/2010 Zhu et al. (73) 7,754,888 B2 7/2010 Loso et al. IN (US) 2005/0228027 A1 10/2005 Zhu et al. 2007/0203191 A1 8/2007 Loso et al. (*) Notice: Subject to any disclaimer, the term of this 2007/0299264 A1 12/2007 Huang et al. patent is extended or adjusted under 35 2008/0033180 A1 2/2008 Renga et al. U.S.C. 154(b) by 264 days. 2008/0058390 A1 3/2008 Loso et al. 2008/0108665 A1 5/2008 Huang et al. This patent is subject to a terminal dis FOREIGN PATENT DOCUMENTS claimer. GB 1307271 A 2/1973 (21) Appl. N0.: 12/150,s01 W0 WO 2006/060029 A 6/2006 (22) Filed: May 1, 2008 OTHER PUBLICATIONS Williams, Trevor et al., Biocontrol Science and Technology, “Is the (65) Prior Publication Data Naturally Derived Insecticide Spinosad Compatible with Insect US 2009/0325892 A1 Dec. 31, 2009 Natural Enemies”, Aug. 2003, vol. 13, No. 15, pp. 459-475.* PCT/US2008/00513, Feb. 23, 2009, DoW AgroSciences LLC, PCT Related US. Application Data International Search Report and Written Opinion. (60) Provisional application No. 60/927,119, ?led on May * cited by examiner 1, 2007. Primary Examiner * Shaojia Anna Jiang Int. Cl. (51) Assistant Examiner * Bahar Schmidtmann A01N 33/02 (2006.01) (74) Attorney, Agent, or Firm * Carl D. Corvin; Craig E. A01N 57/16 (2006.01) Mixan A01N 39/00 (2006.01) A01N 53/10 (2006.01) A01P 7/04 (2006.01) (57) ABSTRACT (52) US. Cl. ........... .. 514/28; 514/89; 514/506; 514/615 Synergistic pesticidal mixtures are provided. (58) Field of Classi?cation Search .................. .. 514/28, 514/89, 506, 615 See application ?le for complete search history. 4 Claims, No Drawings US 7,960,354 B2 1 SYNERGISTIC PESTICIDAL MIXTURES (I) / X CROSS REFERENCE TO RELATED APPLICATIONS This applications claims priority from US. Provisional application 60/927,119 ?led on May 1, 2007, the entire dis closure of Which is hereby incorporated by reference. Wherein X represents NO2, CN or COOR4; L represents a single bond or R1, S and L taken together FIELD OF THE INVENTION represent a 5- or 6-membered ring; R1 represents methyl or ethyl; The invention disclosed in this document is related to ?eld R2 and R3 independently represent hydrogen, methyl, of pesticides and their use in controlling pests. ethyl, ?uoro, chloro or bromo; n is an integer from 0-3; BACKGROUND OF THE INVENTION Y represents 6-halopyridin-3-yl, 6-(Cl-C4)alkylpyridin-3 yl, 6-halo(Cl-C4)alkylpyridin-3-yl, 6-(Cl-C4)alkoxypyridin 3-yl, 6-halo(C1-C4)alkoxypyridin-3-yl, 2-chlorothiaZol-4-yl, Pests cause millions of human deaths around the World 20 each year. Furthermore, there are more than ten thousand or 3-chloroisoxaZol-5-yl When n:0-3 and L represents a species of pests that cause losses in agriculture. These agri single bond, orY represents hydrogen, Cl-C4 alkyl, phenyl, cultural losses amount to billions of US. dollars each year. 6-halopyridin-3-yl, 6-(Cl-C4)alkylpyridin-3-yl, 6-halo(Cl Termites cause damage to various structures such as homes. C4)alkylpyridin-3-yl, 6-(C1-C4)alkoxypyridin-3-yl, 6-halo These termite damage losses amount to billions of US. dol 25 (Cl-C4)alkoxypyridin-3-yl, 2-chlorothiaZol-4-yl, or 3-chlor lars each year. As ?nal note, many stored food pests eat and oisoxaZol-5-yl When n:0-l and R1, S and L taken together adulterate stored food. These stored food losses amount to represent a 5- or 6-membered ring; and billions of US. dollars each year, but more importantly, R4 represents C l-C3 alkyl. deprive people of needed food. Methods for the preparation of sulfoximines, other than There is an acute need for neW pesticides. Insects are devel 30 those described in Scheme H, have been previously disclosed oping resistance to pesticides in current use. Hundreds of in US Patent Publication 20050228027, Whose teachings are insect species are resistant to one or more pesticides. The incorporated herein. development of resistance to some of the older pesticides, The compounds of formula (Ia), Wherein R1, R2, R3 , R4, X, such as DDT, the carbamates, and the organophosphates, is andY are as previously de?ned and L is a single bond, can be Well knoWn. But resistance has even developed to some of the 35 prepared by the methods illustrated in Scheme A: neWer pesticides. Therefore, a need exists for neW pesticides and particularly for pesticides that have neW modes of action. Substituents (Non-Exhaustive List) 40 The examples given for the substituents are (except for mCPBA NaN3x halo) non-exhaustive and must not be construed as limiting (A) (B) H2804 the invention disclosed in this document. x 0 NH 0 / “alkoxy” means an alkyl further consisting of a carbon 45 oxygen single bond, for example, methoxy, ethoxy, propoxy, R1 isopropoxy, l-butoxy, 2-butoxy, isobutoxy, tert-butoxy, pen toxy, 2-methylbutoxy, l,l-dimethylpropoxy, hexoxy, hep toxy, octoxy, nonoxy, and decoxy. 50 “alkyl” means an acyclic, saturated, branched or In step a of Scheme A, sul?de of formula (A) is oxidiZed unbranched, substituent consisting of carbon and hydrogen, for example, methyl, ethyl, propyl, isopropyl, l-butyl, 2-bu With meta-chloroperoxybenZoic acid (mCPBA) in a polar tyl, isobutyl, tert-butyl, pentyl, 2-methylbutyl, l,l-dimethyl solvent below 00 C. to provide sulfoxide of formula (B). In propyl, hexyl, heptyl, octyl, nonyl, and decyl. most cases, dichloromethane is the preferred solvent for oxi 55 dation. “halo” means ?uoro, chloro, bromo, and iodo. In step b of Scheme A, sulfoxide (B) is iminated With “haloalkyl” means an alkyl further consisting of, from one sodium aZide in the presence of concentrated sulfuric acid in to the maximum possible number of, identical or different, an aprotic solvent under heating to provide sulfoximine of halos, for example, ?uoromethyl, di?uoromethyl, tri?uorom formula (C). In most cases, chloroform is the preferred sol ethyl, l-?uoromethyl, 2-?uoroethyl, 2,2,2-tri?uoroethyl, 60 vent for this reaction. chloromethyl, trichloromethyl, and l , l ,2,2-tetra?uoroethyl. In step c of Scheme A, the nitrogen of sulfoximine (C) can be either cyanated With cyanogen bromide in the presence of a base, or nitrated With nitric acid in the presence of acetic DETAILED DESCRIPTION OF THE INVENTION anhydride under mildly elevated temperature, or carboxy 65 lated With alkyl (R4) chloroformate in the presence of base Compounds of the folloWing formula are synergistic With a such as 4-dimethylaminopyridine (DMAP) to provide N- sub variety of other pesticides. stituted sulfoximine (Ia). Base is required for e?icient cyana US 7,960,354 B2 3 4 tion and carboxylation and the preferred base is DMAP, The starting sul?des (A) in Scheme A can be prepared in Whereas sulfuric acid is used as catalyst for ef?cient nitration different Ways as illustrated in Schemes D, E, F G, H, and I. reaction. In Scheme D, the sul?de of formula (Al), Wherein R1, R2 The compounds of formula (Ia), Wherein X represents CN and Y are as previously de?ned, n:l, and R3:H, can be and R1, R2, R3, R4 andY are as previously de?ned, can be 5 prepared from the chloride of formula (D1) by nucleophilic prepared by the mild and e?icient method illustrated in substitution With the sodium salt of an alkyl thiol. Scheme B. 3. SchemeD Rl R2 R2 (A) Y Y RlsNa N/ CN 01 R1 s (D1) (A1) Z 3 b S — L — (CRRh _ Y —>mCPBA,K2CO3 l Or 20 R RuCl3,NaIO4 (F) CN N/ In Scheme E, the sul?de of formula (A2), Wherein R1, R2 and Y are as previously de?ned, n:3, and R3:H, can be 25 prepared from the chloride of formula (D2) by reacting With a 2-mono substituted methyl malonate in the presence of base such as potassium tert-butoxide to provide 2,2-disubstitued malonate, hydrolysis under basic conditions to form a diacid, decarboxylation of the diacid by heating to give a monoacid, In step a of Scheme B, sul?de is oXidiZed With iodobenZene 30 reduction of the monoacid With borane-tetrahyrofuran com diacetate in the presence of cyanamide at 0° C. to give sul?l plex to provide an alcohol, tosylation of the alcohol With imine (F). The reaction can be carried out in a polar aprotic toluenesulfonyl chloride (tosyl chloride) in the presence of a solvent like dichloromethane. base like pyridine to give a tosylate and replacement of the tosylate With the sodium salt of the desired thiol. In step b of Scheme B, the sul?limine (F) is oXidiZed With 35 mCPBA. A base such as potassium carbonate is employed to neutraliZe the acidity of mCPBA. Protic polar solvents such as ethanol and Water are used to increase the solubility of the sul?limine starting material and the base employed.
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