N-substituted azacycles
View Patent ↗N-substituted azacycle derivative compounds represented by formula (I): wherein m, q, r, t and u are independently selected from 0 or 1; and p is 0, 1, 2, or 3; and A, B, D, X, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are fully described herein. The compounds being particularly useful in compositions comprising an insecticidally effective amount of at least one compound of formula I, and an 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 m, q and p are 0; t and u are 1; A is —CH 2 —; X is selected from halogen, hydroxyl or alkoxycarbonyl; Y is selected from hydrogen, halogen or hydroxyl; R 1 , R 2 , R 3 and R 4 are independently selected from hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, —CH 2 (OH)CH 3 , —CH═NOC 2 H 5 , 1,3-dioxolan-2-yl, or R 2 and R 3 taken together with —OCF 2 O—; R 5 is hydrogen; R 7 , R 10 and R 11 are hydrogen; R 8 is selected from hydrogen, halogen, alkyl or alkoxy; R 9 is selected from alkoxy, alkoxyalkoxy, alkoxyalkoxyalkoxy, cyclopropylmethoxy, 2-halophenoxy, 3-halophenoxy, 4-halophenoxy, pyrimidin-2-yl, pyrid-2-yl, 3-halo-pyrid-2-yl, 3-alkyl-pyrid-2-yloxy, 4-alkyl-pyrid-2-yloxy, 5-alkyl-pyrid-2-yloxy, 6-alkyl-pyrid-2-yloxy, 3-halo-pyrid-2-yloxy, 3-trihaloalkyl-pryid-2-yloxy, 3-cyano-pyrid-2-yloxy, 5-cyano-pyrid-2-yloxy, 6-dialkoxyalkyl-pyrid-2-yloxy, pyrid-2-yloxy, CO 2 CH(CH 3 ) 2 , —CH═NOCH 3 , —CH═NOC 2 H 5 , —CH═NOCH 2 CF 3 , —CH═NOCH 2 CH═CH 2 , —CH═NOCH 2 CN, —CH═NOCH(CH 3 ) 2 , —CH═NOCH 2 C≡CH, —CH═NOCH 2 CH 2 F, —CH═NOCH 2 CH 2 OCH 3 , —CH═NOCH 2 OC 2 H 5 , —CH═NOCH 2 CH 2 OCH 2 CH 2 OCH 3 , —NHCO 2 CH 3 , —NHCO 2 C 2 H 5 , —NHCO 2 CH(CH 3 ) 2 , —NHCO 2 CH 2 -c-C 3 H 5 , —CH(OH)C 6 H 5 -p-Cl, —OC(═O)NHCH 3 , —OC(═O)NHC 2 H 5 , —OC(═O)NHCH(CH 3 ) 2 , —NHC(SCH 3 )═NCN, pyrimidin-2-yloxy, 6-halo-pyridazin-3-yloxy, 6-alkoxy-pyridazin-3-yloxy, 6-alkyl-pyridazin-3-yloxy, 2-alkyl-2H-tetrazol-5-yl, 1,3-dioxan-2-yl or 5,5-dialkyl-1,3-dioxan-2-yl; and R is phenyl substituted with R 14 , R 15 , R 16 , R 17 , and R 18 ,
where
R 14 , R 15 , R 16 and R 17 are independently selected from halogen, haloalkyl, haloalkoxy or R 15 and R 16 taken together with —OCF 2 O—; and R 18 is hydrogen and
agriculturally-acceptable salts thereof.
2. The compound of claim 1 , wherein X is selected from halogen, —CO 2 C 2 H 5 or hydroxyl; and R 9 is selected from —OC 2 H 5 , —OC 3 H 7 , —OCH(CH 3 ) 2 , —OCH 2 CH 2 OCH 3 , —OCH 2 CH 2 CH 2 OCH 3 , cyclopropylmethoxy, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, pyrimidin-2-yl, pyrid-2-yl, 3-chloro-pyrid-2-yl, 3-methyl-pyrid-2-yloxy, 4-methyl-pyrid-2-yloxy, 5-methyl-pyrid-2-yloxy, 6-methyl-pyrid-2-yloxy, 3-chloro-pyrid-2-yloxy, 3-trifluoromethyl-pryid-2-yloxy, 3-cyano-pyrid-2-yloxy, 5-cyano-pyrid-2-yloxy, 6-dimethoxymethyl-pyrid-2-yloxy, pyrid-2-yloxy, —CO 2 CH(CH 3 ) 2 , —CH═NOCH 3 , —CH═NOC 2 H 5 , —CH═NOCH 2 CF 3 , —CH═NOCH 2 CH═CH 2 , —CH═NOCH 2 CN, —CH═NOCH(CH 3 ) 2 , —CH═NOCH 2 C≡CH, —CH═NOCH 2 CH 2 F, —CH═NOCH 2 CH 2 OCH 3 , —CH═NOCH 2 OC 2 H 5 , —CH═NOCH 2 CH 2 OCH 2 CH 2 OCH 3 , —NHCO 2 CH 3 , —NHCO 2 C 2 H 5 , —NHCO 2 CH(CH 3 ) 2 , —NHCO 2 CH 2 -c-C 3 H 5 , —CH(OH)C 6 H 5 -p-Cl, —OC(═O)NHCH 3 , —OC(═O)NHC 2 H 5 , —OC(═O)NHCH(CH 3 ) 2 , —NHC(SCH 3 )═NCN, pyrimidin-2-yloxy, 6-chloro-pyridazin-3-yloxy, 6-methoxy-pyridazin-3-yloxy, 6-methyl-pyridazin-3-yloxy, 2-methyl-2H-tetrazol-5-yl, 2-ethyl-2H-tetrazol-5-yl, 1,3-dioxan-2-yl or 5,5-dimethyl-1,3-dioxan-2-yl.
3. The compound of claim 2 , wherein X is selected from fluorine, —CO 2 C 2 H 5 or hydroxyl; Y is selected from hydrogen, fluorine, chlorine or hydroxyl; R 1 , R 2 , R 3 and R 4 are independently selected from hydrogen, halogen, alkyl, tert-butyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, —OCF 2 CHFCF 3 , —CH 2 (OH)CH 3 , —CH═NOC 2 H 5 , 1,3-dioxolan-2-yl or R 2 and R 3 taken together with —OCF 2 O—; R 5 is hydrogen; R 9 is selected from —OCH 2 CH 2 OCH 3 , —CH═NOCH 3 , —CH═NOC 2 H 5 , —CH═NOCH 2 CN, —CH═NOCH 2 CH 2 OCH 3 , —NHCO 2 CH(CH 3 ) 2 , —OC(═O)NHCH(CH 3 ) 2 , pyrimidin-2-yl, pyrid-2-yl, 3-chloro-pyrid-2-yl, 3-methyl-pyrid-2-yloxy, 4-methyl-pyrid-2-yloxy, 5-methyl-pyrid-2-yloxy, 6-methyl-pyrid-2-yloxy, 3-chloro-pyrid-2-yloxy, 3-trifluoromethyl-pryid-2-yloxy, 3-cyano-pyrid-2-yloxy, 5-cyano-pyrid-2-yloxy, 6-dimethoxymethyl-pyrid-2-yloxy, pyrid-2-yloxy, pyrimidin-2-yloxy, 6-chloro-pyridazin-3-yloxy, 6-methoxy-pyridazin-3-yloxy or 6-methyl-pyridazin-3yloxy; and R is phenyl substituted with R 14 , R 15 , R 16 , R 17 , and R 18 ,
where
R 14 , R 15 , R 16 and R 17 are independently selected from fluorine, chlorine, trifluoromethyl, difluoromethoxy, trifluoromethoxy, —OCF 2 CHFCF 3 or R 15 and R 16 taken together with —OCF 2 O—.
4. The compound of claim 3 , wherein X is hydroxyl; Y is hydrogen; R 3 is haloalkoxy; R 9 is selected —OCH 2 CH 2 OCH 3 , —CH═NOCH 3 , —CH═NOC 2 H 5 , —CH═NOCH 2 CN, —CH═NOCH 2 CH 2 OCH 3 , —NHCO 2 CH(CH 3 ) 2 , —OC(═O)NHCH(CH 3 ) 2 , pyrid-2-yloxy, pyrid-2-yl, 3-cyano-pyrid-2-yloxy, 5-methyl-pyrid-2-yloxy, pyrimidin-2-yloxy, pyrimidin-2-yl, 6-chloro-pyridazin-3-yloxy or 6-methoxy-pyridazin-3-yloxy; and R 16 is haloalkoxy.
5. A compound of formula I:
wherein;
r is selected from 0 or 1; m, q and p are 0; t and u are 1;
A is —CH 2 —;
X is selected from halogen or hydroxyl;
Y is selected from hydrogen or hydroxyl;
R 1 , R 2 , R 3 and R 4 are independently selected from hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or —CH═NOC 2 H 5 ;
R 5 is hydrogen;
R 7 , R 8 , R 10 and R 11 are hydrogen;
R 9 is selected from —OC 2 H 5 , —OC 3 H 7 , —OCH(CH 3 ) 2 , —OCH 2 CH 2 OCH 3 , —OCH 2 CH 2 CH 2 OCH 3 , cyclopropylmethoxy, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, pyrimidin-2-yl, pyrid-2-yl, 3-chloro-pyrid-2-yl, 3-methyl-pyrid-2-yloxy, 4-methyl-pyrid-2-yloxy, 5-methyl-pyrid-2-yloxy, 6-methyl-pyrid-2-yloxy, 3-chloro-pyrid-2-yloxy, 3-trifluoromethyl-pryid-2-yloxy, 3-cyano-pyrid-2-yloxy, 5-cyano-pyrid-2-yloxy, 6-dimethoxymethyl-pyrid-2-yloxy, pyrid-2-yloxy, CO 2 CH(CH 3 ) 2 , —CH═NOCH 3 , —CH═NOC 2 H 5 , —CH═NOCH 2 CF 3 , —CH═NOallyl, —CH═NOCH 2 CH═CH 2 , —CH═NOCH 2 CN, —CH═NOCH(CH 3 ) 2 , —CH═NOCH 2 C≡CH, —CH═NOCH 2 CH 2 F, —CH═NOCH 2 CH 2 OCH 3 , —CH═NOCH 2 OC 2 H 5 , —CH═NOCH 2 CH 2 OCH 2 CH 2 OCH 3 , —NHCO 2 CH 3 , —NHCO 2 C 2 H 5 , —NHCO 2 CH(CH 3 ) 2 ,—NHCO 2 CH 2 -c-C 3 H 5 , —CH(OH)C 6 H 5 -p-Cl, —OC(═O)NHCH 3 , —OC(═O)NHC 2 H 5 , —OC(═O)NHCH(CH 3 ) 2 , —NHC(SCH 3 )═NCN, pyrimidin-2-yloxy, 6-chloro-pyridazin-3-yloxy, 6-methoxy-pyridazin-3-yloxy, 6-methyl-pyridazin-3-yloxy, 2-methyl-2H-tetrazol-5-yl, 2-ethyl-2H-tetrazol-5-yl, 1,3-dioxan-2-yl or 5,5-dimethyl-1,3-dioxan-2-yl; and
R is phenyl substituted with R 14 , R 15 , R 16 , R 17 , and R 18 ,
where
R 16 is selected from haloalkyl or haloalkoxy, and R 14 , R 15 , R 17 and R 18 are hydrogen.
6. A compound of formula I-H:
wherein,
R 3 is haloalkyl or haloalkoxy;
R 9 is selected from —OCH 2 CH 2 OCH 3 , pyrid-2-yloxy, pyrid-2-yl, 3-cyano-pyrid-2-yloxy, 5-methyl-pyrid-2-yloxy, pyrimidin-2-yloxy, pyrimidin-2-yl, 6-chloro-pyridazin-3-yloxy or 6-methoxy-pyridazin-3-yloxy; and
R 16 is haloalkyl or haloalkoxy.
7. A compound of formula I-J:
wherein,
R 3 is haloalkyl or haloalkoxy;
R 9 is selected from —OCH 2 CH 2 OCH 3 , pyrid-2-yloxy, pyrid-2-yl, 3-cyano-pyrid-2-yloxy, 5-methyl-pyrid-2-yloxy, pyrimidin-2-yloxy, pyrimidin-2-yl, 6-chloro-pyridazin-3-yloxy or 6-methoxy-pyridazin-3-yloxy; and
R 16 is haloalkyl or haloalkoxy.
8. The compound:
namely, 4-{bis[4-(trifluoromethoxy)phenyl]methyl}-4-hydroxy-1-[(4-(2-pyridyloxy)phenyl)methyl]piperidin-1-oxide, and agriculturally-acceptable salts thereof.
9. A composition containing an insecticidally effective amount of a compound of claim 1 in admixture with at least one agriculturally acceptable extender or adjuvant.
10. A composition containing an insecticidally effective amount of a compound of claim 2 in admixture with at least one agriculturally acceptable extender or adjuvant.
11. A composition containing an insecticidally effective amount of a compound of claim 3 in admixture with at least one agriculturally acceptable extender or adjuvant.
12. A composition containing an insecticidally effective amount of a compound of claim 4 in admixture with at least one agriculturally acceptable extender or adjuvant.
13. A composition containing an insecticidally effective amount of a compound of claim 5 in admixture with at least one agriculturally acceptable extender or adjuvant.
14. A composition containing an insecticidally effective amount of a compound of claim 6 in admixture with at least one agriculturally acceptable extender or adjuvant.
15. A composition containing an insecticidally effective amount of a compound of claim 7 in admixture with at least one agriculturally acceptable extender or adjuvant.
16. A composition containing an insecticidally effective amount of a compound of claim 8 in admixture with at least one agriculturally acceptable extender or adjuvant.
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.
21. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 13 to a locus where insects are present or are expected to be present.
22. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 14 to a locus where insects are present or are expected to be present.
23. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 15 to a locus where insects are present or are expected to be present.
24. A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 16 to a locus where insects are present or are expected to be present.