Pesticidal heterocycles
View Patent ↗It has now been found that certain novel heterocyclic derivatives have provided unexpected insecticidal activity. These compounds are represented by formula (I): R Preferred are those compounds of formula (I) where R 2 and R3 taken together is ═NCH(R 6 )CH(R 7 )N(R 8 )—, ═NC(R6)═C(R7)N(R8)—, or ═CHN═C(R 7 )N(R 8 )—, and tautomers thereof, and where R 4 and R 5 taken together is —C(R11)═C(R12)C(R13)═C(R14) 1 12, —, where R,R,R 6, R 7, R8, R I1, R R 13, R 14, and X are described. 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:
wherein
—R and R 1 are hydrogen;
—R 2 and R 3 are taken together to form ═NCH(R 6 )CH(R 7 )N(R 8 )—, and tautomers thereof;
where
R 6 and R 7 are hydrogen;
R 8 is hydrogen,
—R 4 and R 5 taken together are —C(R 11 )═C(R 12 )C(R 13 )═C(R 14 )—,
where
R 11 is hydrogen, R 14 is hydrogen, halogen or methyl;
R 12 is selected from hydrogen, halogen, (C 1 -C 2 )alkyl, methoxy,
R 13 is hydrogen, halogen, cyano, (C 1 -C 2 )alkyl, hydroxy, or halomethyl, and,
—X is —CHR 17 — or —CH 2 CHR 17 —,
where
R 17 is selected from hydrogen and alkyl; and
agriculturally-acceptable salts thereof;
with the proviso that when R and R 1 are hydrogen; R 2 and R 3 taken together is ═NCH(R 6 )CH(R 7 )N(R 8 )—; where R 6 , R 7 , and R 8 are hydrogen; R 4 and R 5 taken together is —C(R 11 )═C(R 12 )C(R 13 )═C(R 14 )—, and X is —CHR 17 , where R 17 is hydrogen; then i) when R 11 , R 13 and R 14 are hydrogen, then R 12 is other than methyl; ii) when R 11 is hydrogen, R 13 is methyl, and R 14 is H, then R 12 is other than hydrogen; iii) when R 11 and R 14 are hydrogen, and R 12 is methoxy, then R 13 is other than methoxy, and iv) when X is —CH 2 CHR 17 —, R 17 is hydrogen; R 11 and R 14 are hydrogen, R 12 is methoxy, and R 13 is methyl; then R 8 is H.
2. The compound of claim 1 , wherein R 2 and R 3 taken together is ═NCH(R 6 )CH(R 7 )N(R 8 )—, and tautomers thereof, where R 8 is hydrogen, R 4 and R 5 taken together are —C(R 11 )═C(R 12 )C(R 13 )═C(R 14 ), where R 11 is hydrogen, R 12 is halogen or methoxy, and R 13 is (C 1 -C 2 )alkyl; and, X is —CHR 17 — or —CH 2 CHR 17 —.
3. The compound of claim 2 , wherein R 12 is chlorine or methoxy; R 13 is chlorine or methyl; R 14 is hydrogen or methyl; and X is —CH 2 CHR 17 , where R 17 is hydrogen.
4. The compound of claim 3 , wherein R 2 and R 3 taken together is ═NCH(R 6 )CH(R 7 )N(R 8 )—.
5. An insecticidal composition comprising at least one of an insecticidally effective amount of a compound of formula I and at least one insecticidally compatible carrier therefor, wherein the compound of formula I is:
wherein
—R and R 1 are hydrogen;
—R 2 and R 3 are taken together to form ═NCH(R 6 )CH(R 7 )N(R 8 )—, and tautomers thereof;
where
R 6 and R 7 are hydrogen;
R 8 is hydrogen,
—R 4 and R 5 taken together are —C(R 11 )═C(R 12 )C(R 13 )═C(R 14 )—,
where
R 11 is hydrogen, R 14 is hydrogen or methyl;
R 12 is selected from hydrogen, halogen, (C 1 -C 2 )alkyl, methoxy,
R 13 is hydrogen, halogen, cyano, (C 1 -C 2 )alkyl, or halomethyl, and,
—X is —CHR 17 —or —CH 2 CHR 17 —,
where
R 17 is selected from hydrogen and alkyl; and
agriculturally-acceptable salts thereof;
with the proviso that when R and R 1 are hydrogen; R 2 and R 3 taken together is ═NCH(R 6 )CH(R 7 )N(R 8 )—; where R 6 , R 7 , and R 8 are hydrogen; R 4 and R 5 taken together is —C(R 11 )═C(R 12 )C(R 13 )═C(R 14 )—, and X is —CHR 17 , where R 17 is hydrogen; then i) when R 11 , R 13 and R 14 are hydrogen, then R 12 is other than methyl; ii) when R 11 is hydrogen, R 13 is methyl, and R 14 is H, then R 12 is other than hydrogen; iii) when R 11 and R 14 are hydrogen, and R 12 is methoxy, then R 13 is other than methoxy, and iv) when X is —CH 2 CHR 7 —, R 17 is hydrogen; R 11 and R 14 are hydrogen, R 12 is methoxy, and R 13 is methyl; then R 8 is H.
6. An insecticidal composition of claim 5 , wherein R 2 and R 3 taken together is ═NCH(R 6 )CH(R 7 )N(R 8 )—, and tautomers thereof, where R 8 is hydrogen, R 4 and R 5 taken together are —C(R 11 )═C(R 12 )C(R 13 )═C(R 14 ), where R 11 is hydrogen, R 12 is selected from halogen and methoxy, and R 13 is (C 1 -C 2 )alkyl; and X is —CHR 17 —or —CH 2 CHR 17 —.
7. An insecticidal composition of claim 6 , wherein R 9 and R 10 are each methyl; R 12 is selected from chlorine and methoxy; R 13 is methyl; R 14 is hydrogen or methyl; and X is —CH 2 CHR 17 — where R 17 is hydrogen.
8. An insecticidal composition of claim 7 , wherein R 2 and R 3 taken together is ═NCH(R 6 )CH(R 7 )N(R 8 )—.
9. An insecticidal composition of claim 5 , further comprising one or more second compounds.
10. An insecticidal composition of claim 6 , further comprising one or more second compounds.
11. An insecticidal composition of claim 7 , further comprising one or more second compounds.
12. An insecticidal composition of claim 8 , further comprising one or more second compounds.
13. 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.
14. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 6 to a locus where insects are present or are expected to be present.
15. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 7 to a locus where insects are present or are expected to be present.
16. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 8 to a locus where insects are present or are expected to be present.
17. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 9 to a locus where insects are present or are expected to be present.
18. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 10 to a locus where insects are present or are expected to be present.
19. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 11 to a locus where insects are present or are expected to be present.
20. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 12 to a locus where insects are present or are expected to be present.