US 7,601,674 B2
α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives
Martin Zeller, Muenchwilen (Switzerland); Clemens Lamberth, Basel (Switzerland); and Miroslav Kriz, Bratislava (Slovakia (Slovak Republic))
Assigned to Syngenta Crop Protection, Inc., Greensboro, N.C. (US)
Appl. No. 10/495,094
PCT Filed Nov. 15, 2002, PCT No. PCT/EP02/12845
§ 371(c)(1), (2), (4) Date May 07, 2004,
PCT Pub. No. WO03/042167, PCT Pub. Date May 22, 2003.
Claims priority of application No. 0127556.9 (GB), filed on Nov. 16, 2001.
Prior Publication US 2005/0020450 A1, Jan. 27, 2005
This patent is subject to a terminal disclaimer.
Int. Cl. A01N 37/18 (2006.01); C07C 233/00 (2006.01)
U.S. Cl. 504—336  [564/170] 11 Claims
 
1. A compound of the formula

OG Complex Work Unit Drawing
the optical isomers and mixtures of such isomers thereof, wherein A is phenyl, naphthyl, 1,3-biphenyl, 1,4-biphenyl, fluorenyl, tetralinyl, indanyl, methylendioxyphenyl or (1,2-ethylene)dioxyphenyl, each optionally substituted by one or more substituents selected from the group consisting of C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C8-cycloalkyl, C1-C8-cycloalkyl-C1-C10-alkyl, phenyl, phenyl-C1-C10-alkyl, C1-C10-alkoxy, C3-C10-alkenyloxy, C3-C10-alkynyloxy, C1-C10-alkylthio, C1-C10-alkylsulfonyl, C1-C10-alkoxy-C1-C10-alkyl, C1-C10-alkanoyl, C1-C10-alkoxycarbonyl, C3-C10-alkenyloxycarbonyl, C3-C10-alkynyloxycarbonyl, C1-C10-alkylamino, di-C1-C10-alkylamino, hydroxy, halogen, cyano, nitro, amino and formyl radicals, wherein in turn the alkyl- alkenyl-, alkynyl- and cycloalkyl-groups may be optionally substituted by one or more halogen atoms;
X is oxygen or sulfur;
Y is oxygen or sulfur;
R1 is hydrogen, C1-C10-alkyl, C3-C10-alkenyl, C3-C10-alkynyl or C3-C8-cycloalkyl, wherein all alkyl- alkenyl-, alkynyl- and cycloalkyl-groups may be optionally substituted by halogen; and
R2 is hydrogen, C1-C10-alkyl, C3-C10-alkenyl, C3-C10-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy-C3-C10-alkenyl or C1-C6-alkoxy-C3-C10-alkynyl, wherein all alkyl- alkenyl-, alkynyl-, or cycloalkyl-groups may be optionally substituted by halogen; or stands for phenyl-C1-C6-alkyl, phenyl-C1-C6-alkenyl or phenyl-C1-C6-alkynyl, wherein phenyl may optionally be mono- or disubstituted by substituents selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkanoyl, C1-C6-alkoxycarbonyl, halogen, cyano, nitro and formyl; and
R3 is hydrogen, C1-C10-alkyl, C3-C10-alkenyl, C3-C10-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy-C3-C10-alkenyl or C1-C6-alkoxy-C3-C10-alkynyl, wherein all alkyl- alkenyl-, alkynyl-, or cycloalkyl-groups may be optionally substituted by halogen; or is phenyl-C1-C6-alkyl, phenyl-C1-C6-alkenyl or phenyl-C1-C6-alkynyl, wherein the phenyl groups are optionally mono- or disubstituted by radicals selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkanoyl, C1-C6-alkoxycarbonyl, halogen, cyano, nitro and formyl; and
R4 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-alkylthio, C1-C6-alkanoyl, C1-C6-alkylamino, di-C1-C6-alkylamino or C1-C6-alkoxycarbonyl, wherein all alkyl- alkenyl or alkynyl-groups may be optionally substituted by halogen; or is halogen, cyano, nitro, amino, formyl or carboxyl; and
R5 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
n is an integer 0, 1, 2, 3, or 4;
B1 represents a bridge member —(CR10R11)q— or —(CHR10R11)r-Z-(CR12R13)s, wherein
q is an integer 2, 3 or 4;
r is an integer 0, 1, 2, 3; s is an integer 1, 2 or 3, provided that (r+s) is either 1, 2 or 3;
Z is —O—, —S—, —SO—, —SO2—, NR6—, —CO—, —OOC—, —COO—, —NR6—CO— or —CO—NR6—;
R6 is hydrogen or C1-C4 alkyl;
R10, R11, R12 and R13 independently of each other are hydrogen or C1-C4 alkyl; and
B2 is an C1-C6-alkylene bridge.