US 7,514,561 B2
Pesticidal 5-(acylamino) pyrazole derivatives
Stefan Schnatterer, Hattersheim (Germany); David William Hawkins, Upminster Essex (United Kingdom); Daniela Jans, Bad Homburg v. d. H. (Germany); Michael Maier, Frankfurt (Germany); Anke Kuhlmann, Leverkusen (Germany); Erich Friedrich Sanwald, Leverkusen (Germany); Maria-Theresia Thönessen, Heidesheim (Germany); and Karl Seeger, Hofheim (Germany)
Assigned to Merial Limited, Duluth, Ga. (US)
Appl. No. 10/537,547
PCT Filed Nov. 12, 2003, PCT No. PCT/EP03/12619
§ 371(c)(1), (2), (4) Date Oct. 21, 2005,
PCT Pub. No. WO2004/049803, PCT Pub. Date Jun. 17, 2004.
Claims priority of application No. 02027062 (EP), filed on Dec. 03, 2003.
Prior Publication US 2006/0135778 A1, Jun. 22, 2006
Int. Cl. A61K 31/4439 (2006.01); A61K 31/4152 (2006.01); C07D 231/28 (2006.01)
U.S. Cl. 546—276.1  [548/366.7] 15 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Drawing
wherein:
R1 is (C1-C6)-haloalkyl, CN, NO2 or halogen;
R2 is H, halogen or CH3;
R3 is (C1-C3)-haloalkyl, (C1-C3)-haloalkoxy or S(O)p—(C1-C3)-haloalkyl;
W is N or C—R4;
R4 is halogen or CH3;
A is (C2-C6)-alkylene or (C2-C6)-haloalkylene;
or is (C3-C6)-alkylene in which a carbon in the chain is replaced by O, S, SO, SO2 or NR8 with the proviso that the replacing group is not bonded to the adjacent R5or carbonyl group; or is
(C2-C6)-alkenylene or (C2-C6)-haloalkenylene; or
is —[(C1-C3)-alkyl]r-aryl-[(C1-C3)-alkyl]s-,
or —[(C1-C3)-alkyl]r-heterocyclyl-[(C1-C3)-alkyl]s-,
or —[(C1-C3)-alkyl]r-(C3-C6)-cycloalkyl-[(C1-C3)-alkyl]s- or —[(C1-C3)-alkyl]r-(C5-C6)-cycloalkenyl-[(C1-C3)-alkyl]s-, in which last four mentioned groups the aryl,
heterocyclyl, cycloalkyl and cycloalkenyl are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, OR11, CN, NO2, S(O)pR10, COR10, COOR10, CONR9R10, SO2NR9R10, NR9R10, OH, SO3H and (C1-C6)-alkylideneimino;
R5 is CONR9R10 or CO2R10 when m is 0 or 1; or R5 is NR9R17 when m is 1;
R6 is (C1-C3)-alkyl or (C1-C3)-haloalkyl;
R7 is H, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C7)-cycloalkyl, COR11, COR12, COR13, —CO2—(C1-C6)-alkyl, —CO2—(CH2)qR11, —CO2—(CH2)qR13, —CO2—(C3-C7)-cycloalkyl, —CO2—(C1-C6)-alkyl-(C3-C7)-cycloalkyl, CO—(C2-C6)-alkenyl, —CH2R11 or CH2R13; or (C1-C6)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen,
(C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C3-C7)-cycloalkyl, S(O)pR14, CO2—(C1-C6)-alkyl, —O(C═O)—(C1-C6)-alkyl, NR9R10, CONR9R10, SO2NR9R10, OH, CN, NO2, OR11, OR13,
NR10COR9, NR10SO2R14 and COR12;
R8 is R9, CO—R9, CO—R11, CO2R12 or CO—(C1-C6)-alkyl substituted by amino;
R9 is H, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C7)-cycloalkyl
or —(C1-C6)-alkyl-(C3-C7)-cycloalkyl;
R10 is R9, —[(C1-C6)-alkyl]q-R11, (C1-C3)-alkoxy-(C1-C3)-alkyl-,
(C1-C3)-alkoxy-(C1-C3)-alkoxy-(C1-C3)-alkyl- or (C1-C3)-alkyl-S(O)p—(C1-C3)-alkyl-; or
R9 and R10 or R9 and R17 each together with the respective attached N atom form a four- to seven-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl and CO2—(C1-C6)-alkyl;
R11 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, OR16, CN, NO2, S(O)pR12, COR9, COOH, COOR12, CONR9R15,
SO2NR9R15, NR9R15, OH, SO3H and (C1-C6)-alkylideneimino;
R12 is (C1-C6)-alkyl or (C1-C6)-haloalkyl;
R13 is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy,
S(O)pR12, OH and oxo;
R14 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C7)-cycloalkyl or —(C1-C6)-alkyl-(C3-C7)-cycloalkyl;
R15 is H, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C7)-cycloalkyl or —(C1-C6)-alkyl-(C3-C7-cycloalkyl;
R16 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, CN, NO2, S(O)pR12, COR15, COOH, COOR12, CONR9R15, SO2NR9R15, NR9R15 and OH;
R17 is R10, CO2(C1-C6)-alkyl, —CH2CO2(C1-C6)-alkyl, CO2CH2R18 or CO(C1-C6)-alkyl;
R18 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl and (C1-C6)-alkoxy;
n and p are each independently 0, 1 or 2;
m and q are each independently 0 or 1;
r and s are each independently 0 or 1; and
each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S;
or a pesticidally acceptable salt thereof.