4″-Deoxy-4″-(s)-amino avermectin derivatives

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai

Reexamination Certificate

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C514S450000

Reexamination Certificate

active

07605134

ABSTRACT:
A description is given of compounds of the formula which in the 4″-position has the (S)-configuration and wherein R1is C1-C12alkyl, C3-C8cycloalkyl; or C2-C12alkenyl; R2is hydrogen, optionally substituted C1-C12alkyl or optionally substituted C2-C12alkenyl; R3is C1-C12alkyl, optionally substituted C1-C12alkyl, optionally substituted C1-C12alkoxy-C1-C12alkyl, optionally substituted C3-C12cycloalkyl, optionally substituted C2-C12alkenyl; optionally substituted C4-C12cycloalkenyl, optionally substituted C2-C12alkynyl; or R2and R3together are a three- to seven-membered alkylene or four- to seven-membered alkenylene bridge in each of which a CH2group may have been replaced by O, S or NR4; X is O or S; R4is C1-C8alkyl, C3-C8cycloalkyl, C2-C8alkenyl, C2-C8alkynyl, benzyl or C(═O)—R5; R5is for example H, OH, SH, C1-C12alkyl, C2-C8alkenyl, C2-C8alkynylyl or C1-C12haloalkyl; and, where appropriate, E/Z isomers, mixtures of E/Z isomers and/or tautomers thereof, in each case in free form or in salt form; to a process for the preparation of, and to the use of, such compounds and isomers and tautomers thereof; to starting compounds for the preparation of compounds of formula (I); to pesticidal compositions in which the active ingredient has been selected from the compounds of formula (I) and tautomers thereof; and to a method of controlling pests using such compositions.

REFERENCES:
patent: 4203976 (1980-05-01), Fisher et al.
patent: 4206205 (1980-06-01), Mrozik et al.
patent: 4427663 (1984-01-01), Mrozik
patent: 4622313 (1986-11-01), Wyvratt, Jr. et al.
patent: 4831016 (1989-05-01), Mrozik et al.
patent: 4874749 (1989-10-01), Mrozik
patent: 4895837 (1990-01-01), Mrozik et al.
patent: 5023241 (1991-06-01), Linn et al.
patent: 5057499 (1991-10-01), Mrozik et al.
patent: 5169839 (1992-12-01), Linn et al.
patent: 5192546 (1993-03-01), Abercrombie et al.
patent: 5208222 (1993-05-01), Meinke et al.
patent: 5229415 (1993-07-01), Linn et al.
patent: 5346698 (1994-09-01), Abercrombie et al.
patent: 5362863 (1994-11-01), Cvetovich
patent: 5436355 (1995-07-01), Demchak et al.
patent: 5945445 (1999-08-01), Barringer et al.
patent: 5981500 (1999-11-01), Bishop et al.
patent: 6605595 (2003-08-01), Omura et al.
patent: 6875727 (2005-04-01), Hofer et al.
patent: 6933260 (2005-08-01), Piterna et al.
patent: 7250402 (2007-07-01), Omura et al.
patent: 7378399 (2008-05-01), Cassayre et al.
patent: 2006/0140997 (2006-06-01), Pitterna et al.
patent: 2006/0205595 (2006-09-01), Pitterna et al.
patent: 2008/0051353 (2008-02-01), Jung et al.
patent: 001688 (1979-05-01), None
patent: 0089202 (1983-09-01), None
patent: 0259688 (1988-03-01), None
patent: 0266131 (1988-05-01), None
patent: 0301806 (1989-01-01), None
patent: 0340849 (1989-11-01), None
patent: 0343708 (1989-11-01), None
patent: 375393 (1990-06-01), None
patent: 0411897 (1991-06-01), None
patent: 0456509 (1991-11-01), None
patent: 0465121 (1992-01-01), None
patent: 0506331 (1992-09-01), None
patent: 0519731 (1992-12-01), None
patent: 1160252 (2001-12-01), None
patent: WO 93/15099 (1993-08-01), None
patent: WO 95/20877 (1995-08-01), None
patent: WO 96/22300 (1996-07-01), None
patent: WO 02/068441 (2002-09-01), None
patent: WO 02/068442 (2002-09-01), None
patent: WO 03/020738 (2003-03-01), None
patent: WO 03/053988 (2003-07-01), None
patent: WO 2004/067534 (2004-08-01), None
PF Rolfe, KL Dawson, MD Soll, GK Nichols and WG Ryan, “Persistent efficacy of abamectin and doramectin against gastrointestinal nematodes of cattle”, Australian Veterinary Journal, 1997, 75(1), 33-35.
Mrozik et al.;Bioinorganic&Medicinal Letters, vol. 5, No. 20, pp. 2435-2440, 1995.
Fisher,American Chemical Society Symposium, 1997, vol. 658, “Phytochemicals for Pest Control”, pp. 220-238, 1991.
Cvetovich et al.,J. Org. Chem., 1994, 59, pp. 7704-7708.
Search Report (SYN 118/2001).
U.S. Appl. No. 10/568,715, filed Feb. 17, 2006, Kasaba et al.
U.S. Appl. No. 10/560,390, filed Mar. 22, 2006, Pitterna et al.
U.S. Appl. No. 10/544,274, filed Aug. 3, 2005, Cassayre et al.
U.S. Appl. No. 10/544,281, filed Aug. 3, 2005, Quaranta et al.
U.S. Appl. No. 10/543,638, filed Jul. 28, 2005, Pitterna et al.
U.S. Appl. No. 10/543,643, filed Apr. 5, 2006, Pitterna et al.
U.S. Appl. No. 10/513,247, filed Nov. 2, 2004, Tobler et al.
U.S. Appl. No. 10/498,858, filed Jun. 14, 2004, Cassayre et al.
U.S. Appl. No. 11/319,686, filed Dec. 28, 2005, Pitterna et al.
U.S. Appl. No. 11/319,687, filed Dec. 28, 2005, Pitterna et al.
U.S. Appl. No. 10/539,274, filed Mar. 9, 2006, Maienfisch et al.
Yoshua et al.; Simultanious Determination of Residues of Emanectin and Its Metabolites, and Mibimectin, Ivermectin, and Abamectin in Crops by Liquid Chromatography w Fluorescence Detection. Journal of AOAC International vol. 84, No. 3 (910-917).
Wrzesinski et al, Isolation and Identification of Residues of 4″-(epi-Methylamino)-4″-deoxyavermectin B1a Benzoate from the Surface of Cabbage, Journal of Agricultural and Food Chemistry, vol. 44, 1996, pp. 304-312.
Meinke et al., “Affinity Probes for the Avermectin Binding Proteins”, J Med Chem 1992, 35, 3879-3884.
Jones, T K et al.; “Synthesis and Biological Activity of 4a,4-Disubstituted Avermectins”; Journal of Agriculture and Food Chemistry., American Chemical Society, 42 1994, p. 1786-1790.
Meinke et al. “Synthesis of Avermectin B1-4′-4′a -oxide; A Precursor to Potent Antihelmintic agents”, Biorganic Medicinal Chemistry Letters, vol. 2, 1992 p. 537.
Mrozik, H et al. “Avermectin Acyl Derivatives with Anti helmintic activity” Journal of Medicinal Chemistry, vol. 25, 1982, pp. 658-663.
Shoop et al Efficacy in Sheep and Pharmacokinetics in Cattle That Led to the Selection of Epinomectin as a Topical Endetocide for Cattle, International Journal for Parasitology, 1996, 26 (11), 1227-35.

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