Phenylalkyl substituted heteroaryl derivatives
View Patent ↗Certain novel phenylalkyl substituted azole derivatives have unexpected insecticidal activity. These compounds are represented by formula I: where A, B, D, E, G, a, b, c, d, and R through R 11 , inclusively, are folly described herein. In addition, compositions comprising an insecticidally effective amount of at least one compound of formula I, and optionally, an effective amount of at least one of a second compound, with at least one insecticidally compatible carrier are also disclosed; along with methods of controlling insects comprising applying said compositions to a locus where insects are present or are expected to be present.
1. A compound of formula I
where
R and R 3 are independently selected from hydrogen and halogen;
R 1 and R 2 are independently selected from hydrogen, halogen and (C 1 -C 3 )alkyl;
A is (CH 2 ) f where f is 1;
B is O;
R 4 is hydrogen;
R 5 and R 6 are independently selected from halogen;
a is 1;
and when a is 1,
D is O;
b is 2;
R 7 and R 8 are hydrogen;
E is selected from
where 1 and 2 indicate the bond of attachment in formula I,
c is 0;
d is 0; and,
G is O;
R 11 is
wherein R 21 through R 25 are independently selected from hydrogen, halogen, (C 1 -C 6 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, halo(C 1 -C 6 )alkyl, hydroxy(C 1 -C 6 )alkyl, cyclo(C 3 -C 6 )alkyl, halo(C 2 -C 4 )alkenyl, halo(C 2 -C 4 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl, (C 2 -C 4 )alkenyloxy, (C 2 -C 4 )alkynyloxy, halo(C 1 -C 6 )alkoxy, halo(C 2 -C 4 )alkenyloxy, halo(C 2 -C 4 )alkynyloxy, (C 1 -C 6 )alkylthio, pentahalothio, (C 1 -C 6 )alkylsulfinyl, (C 1 -C 6 )alkylsulfonyl, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkylsulfonyl, cyano, nitro; NR c R d , where R c and R d are independently selected from hydrogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylcarbonyl, and (C 1 -C 6 )alkoxycarbonyl, or R c and R d are taken together to form a 5- or 6-membered saturated or unsaturated ring containing carbon, O, N, or S; (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarbonyloxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkoxycarbonyloxy, (C 1 -C 6 )alkylaminocarbonyl, (C 1 -C 6 )alkylaminocarbonyloxy, tri(C 1 -C 6 )alkylsilyl, di(C 1 -C 6 )alkylphosphinoyl, aryl, aryloxy, and aryl(C 1 -C 6 )alkoxy;
or an
agriculturally-acceptable salt thereof.
2. A compound of claim 1 , wherein
R and R 3 are halogen;
R 1 , R 2 and R 4 are hydrogen;
R 5 and R 6 are halogen;
A is (CH 2 ) f where f is 1;
B is O;
a is 1; D is O;
b is 2; R 7 and R 8 are each hydrogen;
E is formula (E1), formula (E2), formula (E4), formula (E7) or formula (E8);
c is 0; R 9 and R 10 are each hydrogen;
d is 0; and
R 11 is formula (R 11 −1).
3. A compound of claim 2 , wherein
R and R 3 are each chlorine;
a is 1 and D is O;
b is 2;
E is formula (E1) or formula (E7);
c is 0;
d is 0; and
R 11 is (R 11 −1).
4. A composition comprising an insecticidally effective amount of a compound of claim 1 and at least one agriculturally acceptable extender or adjuvant.
5. The insecticidal composition of claim 4 , further comprising one or more additional compounds selected from the group consisting of pesticides, plant growth regulators, fertilizers and soil conditioners.
6. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 4 to a locus where insects are present or are expected to be present.
7. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 5 to a locus where insects are present or are expected to be present.