US 7,569,727 B2
Pesticidally active ketone and oxime derivatives
Werner Zambach, Basel (Switzerland); Roger Graham Hall, Basel (Switzerland); Peter Renold, Basel (Switzerland); and Stephan Trah, Basel (Switzerland)
Assigned to Syngenta Crop Protection, Inc., Greensboro, N.C. (US)
Filed on Apr. 07, 2008, as Appl. No. 12/98,594.
Application 12/098594 is a continuation of application No. 10/560292, abandoned, previously published as PCT/EP2004/006749, filed on Jun. 22, 2004.
Claims priority of application No. 1096/03 (CH), filed on Jun. 23, 2003.
Prior Publication US 2008/0200525 A1, Aug. 21, 2008
Int. Cl. C07C 251/32 (2006.01); C07D 213/24 (2006.01); A01N 33/24 (2006.01); A01N 43/40 (2006.01)
U.S. Cl. 564—253  [564/211; 564/256; 546/334; 514/345; 514/628; 514/640] 7 Claims
 
1. A compound of formula

OG Complex Work Unit Drawing
wherein
A0, A1 and A2 are each a bond;
A3 is a C1-C6alkylene bridge which is unsubstituted;
Y is O;
M is NOR6,
X1 and X2 are each independently of the other fluorine, chlorine or bromine;
R1, R2 and R3 are each independently of the others H, halogen, OH, SH, CN, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6alkynyloxy, —S(═O)—C1-C6alkyl, —S(═O)2—C1-C6alkyl, C1-C6alkoxycarbonyl or C3-C6haloalkynyloxy; the substituents R3 being independent of one another when m is 2;
Q is O;
W is O;
T is a bond;
D is CH or N;
R4 is H, halogen, OH, SH, CN, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6alkynyloxy, —S(═O)—C1-C6alkyl, —S(═O)2—C1-C6alkyl, C1-C6alkoxycarbonyl, C3-C6haloalkynyloxy, NH2, NH(C1-C6alkyl) or N(C1-C6alkyl)2 wherein the two alkyl groups are independent of one another; the substituents R4 being independent of one another when k is greater than 1;
R5 is C1-C12alkoxyC1-C12alkyl or;
R6 is H, C1-C12alkyl, C3-C8cycloalkyl, C1-C6alkylcarbonyl, C2-C6alkenyl, C2-C6alkynyl, aryl, heterocyclyl or benzyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl radicals are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five identical or different substituents selected from the group consisting of halogen, —N3, CN, NO2, OH, SH, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C3-C6alkynyloxy, C3-C6haloalkynyloxy, C3-C8cycloalkyl-C1-C6alkoxy, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl-C1-C6alkyl, C1-C6alkoxycarbonyl-C1-C6alkyl, C1-C6alkylthio, C2-C6alkenylthio, C3-C6alkynylthio, C3-C6cycloalkyl-C1-C6alkylthio, C3-C6haloalkynyl, C2-C6haloalkenylthio, C1-C6haloalkylthio, C1-C6alkoxy-C1-C6alkyl, C1-C6haloalkoxy-C1-C6alkyl, C2-C6alkenyloxy-C1-C6alkyl, C2-C6haloalkenyloxy-C1-C6alkyl, C3-C6alkynyloxy-C1-C6alkyl, NH2, NH(C1-C6alkyl), N(C1-C6alkyl)2 wherein the two alkyl groups are independent of one another, C1-C6alkylcarbonylamino, C1-C6haloalkylcarbonylamino, C1-C6alkoxycarbonylamino and C1-C6alkylaminocarbonylamino;
and the aryl, heterocyclyl and benzyl radicals are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five identical or different substituents selected from the group consisting of halogen, CN, NO2, OH, SH, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C8cycloalkyl, C3-C8cycloalkyl-C1-C6alkyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C3-C6alkynyloxy, C3-C6haloalkynyloxy, C3-C8cycloalkyl-C1-C6alkoxy, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl-C1-C6alkyl, C1-C6alkoxycarbonyl-C1-C6alkyl, C1-C6alkylthio, C2-C6alkenylthio, C3-C6alkynylthio, C3-C6cycloalkyl-C1-C6alkylthio, C3-C6haloalkynyl, C2-C6haloalkenylthio, C1-C6haloalkylthio, C1-C6alkoxy-C1-C6alkyl, C1-C6haloalkoxy-C1-C6alkyl, C2-C6alkenyloxy-C1-C6alkyl, C2-C6haloalkenyloxy-C1-C6alkyl, C3-C6alkynyloxy-C1-C6alkyl, NH2, NH(C1-C6alkyl), N(C1-C6alkyl)2 wherein the two alkyl groups are independent of one another, C1-C6alkylcarbonylamino, C1-C6haloalkylcarbonylamino, C1-C6alkoxycarbonylamino and C1-C6alkylaminocarbonylamino;
R9 is H, C1-C12alkyl unsubstituted or substituted by from one to five identical or different substituents selected from halogen, CN, NO2, OH, C1-C6alkoxy, C1-C6alkylthio, NH2, NH(C1-C6alkyl), N(C1-C6alkyl)2 wherein the two alkyl groups are independent of one another and C1-C6alkylcarbonylamino; C3-C8cycloalkyl, C1-C6alkylcarbonyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, aryl, heterocyclyl or benzyl, wherein the aryl, heterocyclyl and benzyl radicals are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five substituents selected from the group consisting of halogen, CN, NO2, OH, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C8cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C3-C6alkynyloxy, C3-C6haloalkynyloxy, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, C2-C6alkenylthio, C3-C6alkynylthio, C1-C6alkylthio, C3-C6haloalkynyl, C1-C6haloalkylthio, C1-C6alkoxy-C1-C6alkyl, NH2, NH(C1-C6alkyl), N(C1-C6alkyl)2 wherein the two alkyl groups are independent of one another, C1-C6alkylcarbonylamino, C1-C6haloalkylcarbonylamino, C1-C6alkoxycarbonylamino and C1-C6alkylaminocarbonylamino;
R10 is H, C1-C12alkyl unsubstituted or substituted by from one to five identical or different substituents selected from halogen, CN, NO2, OH, C1-C6alkoxy, C1-C6alkylthio, NH2, NH(C1-C6alkyl), N(C1-C6alkyl)2 and C1-C6alkylcarbonylamino; C3-C8cycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, aryl, heterocyclyl or benzyl, wherein the aryl, heterocyclyl and benzyl radicals are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five identical or different substituents selected from the group consisting of halogen, CN, NO2, OH, SH, C1-C6alkyl, C1-C6haloalkyl, C3-C8cycloalkyl, C1-C6-alkoxy, C1-C6haloalkoxy, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl-C1-C6alkyl, C1-C6alkoxy-C1-C6alkyl, NH2, NH(C1-C6alkyl), N(C1-C6alkyl)2 wherein the two alkyl groups are independent of one another, C1-C6alkylcarbonylamino, C1-C6haloalkylcarbonylamino, C1-C6alkoxycarbonylamino and C1-C6alkylaminocarbonylamino;
k is 0, 1, 2, 3 or 4;
m is 1 or 2; and
or, where applicable, a possible E/Z isomer, E/Z isomeric mixture and/or tautomer thereof, in each case in free form or in salt form.