US 7,514,428 B2
Pesticidal 1-aryl-3-amidoxime-pyrazole derivatives
Uwe Döller, Rodgau (Germany); Klaus Dieter Höbald, Mörfelden-Walldorf (Germany); Michael Maier, Frankfurt (Germany); Anke Kuhlmann, Leverkusen (Germany); and Karl Seeger, Hofheim, Ts (Germany)
Assigned to Merial Limited, Duluth, Ga. (US)
Appl. No. 10/537,466
PCT Filed Nov. 12, 2003, PCT No. PCT/EP03/12620
§ 371(c)(1), (2), (4) Date Nov. 16, 2005,
PCT Pub. No. WO2004/050633, PCT Pub. Date Jun. 17, 2004.
Claims priority of application No. 02027064 (EP), filed on Dec. 03, 2002.
Prior Publication US 2006/0241105 A1, Oct. 26, 2006
Int. Cl. A01N 43/66 (2006.01); C07D 417/02 (2006.01)
U.S. Cl. 514—227.5  [514/235.5; 514/241; 514/252.05; 514/255.05; 514/275; 514/341; 514/406; 544/124; 544/209; 544/333; 544/364; 544/405; 546/275.4; 548/356.1] 18 Claims
 
1. A compound of formula (Ia) or (Ib):

OG Complex Work Unit Drawing
wherein:
R1 is aryl unsubstituted or substituted by one or more R15 radicals; or is R10 or R19;
X and Y are each independently H, (C3-C6)-alkenyl, (C3-C6)-haloalkenyl, (C3-C6)-alkynyl, (C3-C6)-haloalkynyl, (C3-C7)-cycloalkyl, —(C1-C4)-alkyl-(C3-C7)-cycloalkyl, —CO2—(C1-C6)-alkyl, CONR7R8, CONR8R9, —CO2—(CH2)qR7, —(CH2)qR7, —(CH2)qR10, COR8, SO2R13 or COR17; or (C1-C6)-alkyl unsubstituted or substituted by one or more R11 radicals;
W is N, C—CH3 or C-halogen;
R2 is hydrogen, CH3 or halogen;
R3 is halo, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-haloalkoxy, S(O)p—(C1-C3)-haloalkyl or SF5;
R4 is H, (C3-C6)-alkenyl, (C3-C6)-haloalkenyl, (C3-C6)-alkynyl, (C3-C6)-haloalkynyl, (C3-C7)-cycloalkyl, —CO2—(C1-C6)-alkyl, —CO2—(C3-C7)-cycloalkyl, —CO2—(C1-C4)-alkyl-(C3-C7)-cycloalkyl, —CO2—(C3-C6)-alkenyl, —CO2—(CH2)qR7, CONR8R9, —CO2—(CH2)qR10, —(CH2)qR7, —(CH2)qR10, COR8 or COCH2O—(C1-C4)-alkyl; or (C1-C6)-alkyl unsubstituted or substituted by one or more R11 radicals;
R5 is H, (C2-C6)-alkynyl, —CO2—(C1-C6)-alkyl, (C3-C7)-cycloalkyl or —SO2R12; or (C1-C6)-alkyl, (C2-C6)-alkenyl or CO—(C1-C6)-alkyl which last three mentioned groups are unsubstituted or substituted by one or more R11 radicals;
R6 and R13 are each independently (C1-6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl or (C3-C7)-cycloalkyl;
R7 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)qR13 and NR9R14;
R8 is H, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C7)-cycloalkyl, —(C1-C4)-alkyl-(C3-C7)-cycloalkyl, —(CH2)qR7 or —(CH2)qR10;
R9 and R14 are each independently H, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C7)-cycloalkyl or —(C1-C4)-alkyl-(C3-C7)-cycloalkyl; or
R8 and R9 together with the attached N atom form a five- or six-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 halogen;
R10 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)pR13, OH and oxo;
R11 is halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C3-C7)-cycloalkyl, S(O)pR13, —CO2—(C1-C6)-alkyl, —O(C═O)—(C1-C6)-alkyl, CO—(C1-C6)-alkyl, CO—(C1-C6)-haloalkyl, NR8R9, CONR8R9, SO2NR8R9, OH, CN, NO2, OR7, NR8COR14, NR8SO2R13 or OR10;
R12 is (C3-C7)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl or R10; or phenyl unsubstituted or substituted by one or more radicals selected from R15; or is (C1-6)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-6)-alkoxy, (C1-6)-haloalkoxy, (C3-6)-alkenyloxy, (C3-C6)-haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkynyloxy, (C3-C7)-cycloalkyl, S(O)pR7, S(O)pR10, S(O)pR13, CN, NO2, OH, COR8, NR8COR14, NR8SO2R13, CONR8R9, NR8R9, OR7, OR10, R16, R10 and CO2R8;
R15 is halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, CN, NO2, S(O)pR13, NR8R9, COR13, COR7, CONR8R9, SO2NR8R9, R7, SF5, OH, OR7, R18, OR18, SO3H or (C1-C6)-alkylideneimino;
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)pR13, NR8R9, COR13, COR7, CONR8R9, SO2NR8R9, OH, SO3H and (C1-C6)-alkylideneimino;
R17 is (C1-C6)-alkyl which is substituted by (C1-C6)-alkoxy, S(O)p—(C1-C6)-alkyl or S(O)p—(C1-C6)-haloalkyl;
R18 is a heteroaromatic radical selected from the group consisting of pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, imidazolyl and triazolyl, which groups are 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;
R19 is a heteroaromatic radical selected from the group consisting of pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, imidazolyl and triazolyl, which is 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, and which heteroaromatic radical is substituted by R7, R18 or OR7;
m is 1 or 2;
n and p are each independently zero, one or two;
q is zero or one; and
each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 6 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.