Insecticidal triazines and pyrimidines
The present invention describes novel triazines, their related pyrimidines and their use in controlling insects. This invention also includes new synthetic procedures, intermediates for preparing the compounds, pesticide compositions containing the compounds, and methods of controlling insects using the compounds.
1. A compound of Formula (I),
wherein:
Y is N
Z is -aryl, —C 1 -C 8 alkylaryl;
X is —H, —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, —NR i R j or —C 1 -C 8 alkylNR i R j ;
R 2 and R 3 are independently —H or —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, and —C 1 -C 8 alkylNR i R j , but R 2 and R 3 are not both H;
R i and R i are independently —H, or —C 1 -C 8 alkyl;
wherein heterocyclic is a 5-10 member cyclic or bicyclic aromatic or saturated —C 1 -C 8 cycloaliphatic ring moiety containing 1, 2, or 3 heteroatoms selected from N, O, or S;
wherein aryl, —C 3 -C 8 cycloalkyl and heterocyclic are optionally independently substituted with one to five substituents independently selected from -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl; and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN, or —OH.
2. A compound of claim 1 wherein:
halo is Cl or F;
R i and R j are H or —C 1 -C 2 alkyl; and
R 2 and R 3 are independently —H or —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, and —C 1 -C 8 alkylNR i R j ; but when one of R 2 and R 3 are -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, and —C 1 -C 8 alkylNR i R j then the other of either R 2 or R 3 is independently —H or —C 1 -C 8 alkyl.
3. A compound of claim 1 wherein
1 or 2 of X, and either R 2 , or R 3 is independently a —C 1 -C 6 cycloalkyl, —C 1 -C 6 alkylC 6 cycloalkyl, —C 6 aryl, —C 1 -C 6 alkylC 6 aryl or —C 6 heterocyclic or —C 1 -C 6 alkylC 6 -heterocyclic or saturated or unsaturated optionally substituted ring;
Z is —C 6 aryl, or —C 1 -C 8 alkyl-C 6 aryl;
X, Z, and either R 2 , or R 3 is optionally independently substituted with 1, 2 or 3, of —H, -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl; and
at each occurrence, any —C 1 -C 6 alkyl, is optionally independently substituted with 1-5 -halo, —CN or —OH.
4. A compound of claim 3 wherein
1 or 2 of X, and either R 2 , or R 3 is independently a heterocyclic or —C 1 -C 6 alkylheterocyclic 6 member saturated or unsaturated optionally substituted ring;
Z is phenyl;
X, Z, and either R 2 , or R 3 is optionally independently substituted with 1 or 2 —H, -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl; and
at each occurrence, any —C 1 -C 6 alkyl, is optionally independently substituted with 1-5 -halo, —CN or —OH.
5. A compound of claim 3 wherein
1 or 2 of X, and either R 2 , or R 3 is independently a —C 1 -C 6 cycloalkyl, —C 1 -C 6 alkylC 6 cycloalkyl, —C 6 aryl, or a —C 1 -C 6 alkylC 6 aryl;
Z is phenyl;
X, Z, and either R 2 , or R 3 is optionally independently substituted with 1 —H, -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl; and
at each occurrence, any —C 1 -C 6 alkyl, is optionally independently substituted with 1-5 -halo, —CN or —OH.
6. A compound of claim 3 wherein said heterocyclic or alkylheterocyclic is an aromatic unsaturated optionally substituted ring, a aliphatic saturated ring, or a combination of both unsaturated and saturated optionally substituted rings and the hetero atom is a non adjacent N or O or combination of N and O atoms.
7. A compound of claim 3 wherein
Z is -aryl, —C 1 -C 8 alkylaryl;
when R 2 is —H or —C 1 -C 8 alkyl then R 3 is —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, and —C 1 -C 8 alkylNR i R j ; and
when R 3 is —H or —C 1 -C 8 alkyl then R 2 is —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, and —C 1 -C 8 alkylNR i R j ;
R i and R i are independently —H, or —C 1 -C 8 alkyl.
8. A compound of claim 7 wherein
aryl is phenyl, alkylaryl is alkylphenyl and phenyl or alkylphenyl is optionally independently substituted with 1, 2 or 3 -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl;
and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN, or —OH.
9. A compound of claim 8 wherein
X is optionally independently substituted with 1, 2 or 3 -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl;
R 2 or R 3 is optionally independently substituted with 1 or 2 -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl;
Z is optionally independently substituted with 1, 2 or 3 -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl;
and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN, or —OH.
10. A compound of claim 1 wherein the aryl is phenyl and phenyl is optionally substituted with 1-3 R 10 at any of the positions of any of the formula below
wherein:
R 10 is optionally independently selected from -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl; and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN or —OH.
11. A compound of claim 1 wherein
1 or 2 of X, and either R 2 , or R 3 is independently a heterocyclic or alkylheterocyclic 5, 6 or 10 member saturated or unsaturated optionally substituted ring optionally independently substituted with 1, 2 or 3, of —H, -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl;
wherein at each occurrence, any —C 1 -C 6 alkyl, is optionally independently substituted with 1-5 -halo, —CN or —OH.
12. A compound of claim 11 wherein
Z is -aryl, —C 1 -C 8 alkylaryl;
X is heterocyclic or —C 1 -C 8 alkylheterocyclic;
when R 2 is —H or —C i -C 8 alkyl, then R 3 is —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl and —C 1 -C 8 akylNR i R j ; and
when R 3 is —H or —C 1 -C 8 alkyl, then R 2 is —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl and —C 1 -C 8 alkylNR i R j .
13. A compound of claim 11 wherein
Z is -aryl, —C 1 -C 8 alkylaryl;
X is —H, —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, —NR i R j or —C 1 -C 8 alkylNR i R j ;
R 2 is —H or —C i -C 8 alkyl, when R 3 is heterocyclic and —C 1 -C 8 alkylheterocyclic; and
R 3 is —H or —C 1 -C 8 alkyl, when R 2 is -heterocyclic and —C 1 -C 8 alkylheterocyclic.
14. A process for the preparation of a compound comprising:
(a) contacting cyanuric chloride (Formula V),
with an organometallic shown in Formula VII
Z-M Formula VII
wherein
Z is -aryl, or —C 1 -C 8 alkylaryl, and
M is selected from lithium, magnesium, boron, zinc, palladium and tin;
in a polar aprotic solvent to provide an aryl substituted triazine of Formula VIII
wherein
Z is -aryl, or —C 1 -C 8 alkylaryl,
Hal is halo,
(b) contacting a compound of Formula VIII with a primary amino nucleophile (X—NH 2 ) in a polar aprotic solvent in the presence of a base,
X, is —H, —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkyl C 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, —NR i R j or —C 1 -C 8 alkylNR i R j ;
and R i and R j are independently —H or —C 1 -C 8 alkyl,
to provide a compound of Formula XI
wherein,
Z is -aryl, or —C 1 -C 8 alkylaryl,
Hal is halo;
X, is —H, —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, —NR i R j or —C 1 -C 8 alkylNR i R j ;
and R i and R j are independently —H or —C 1 -C 8 alkyl,
(c) contacting the compound of Formula XI with hydrazine in a polar aprotic solvent to provide a hydrazine compound which is then added to a keto compound to make a compound of Formula I
wherein
X, is —H, —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, —NR i R j or —C 1 -C 8 alkylNR i R j ;
wherein heterocyclic is a 5-10 member cyclic or bicyclic aromatic or saturated —C i -C 8 cycloaliphatic ring moiety containing 1, 2, or 3 heteroatoms selected from N, O, or S;
wherein aryl, —C 3 -C 8 cycloalkyl and heterocyclic are optionally independently substituted with one to five substituents independently selected from -halo, —CN, —OH, —OCH 2 CH═CHCl, —C i -C 6 alkyl, O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl; and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN, or —OH;
Y is N;
Z is -aryl, —C 1 -C 8 alkylaryl;
R 2 and R 3 are independently —H or —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, and —C 1 -C 8 alkylNR i R j , but R 2 and R 3 are not both H; and
R i and R j are independently —H, or —C 1 -C 8 alkyl.
15. The compound of claim 1 selected from:
N-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; N-(4-chlorophenyl)-4-phenyl-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(4-chlorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; N-((6-chloropyridin-3-ypmethyl)-4-(2,6-difluorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; N-(6-chloropyridin-3-yl)-4-(2,6-difluorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; N-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-(2-(4-(1,1 ,2,2-tetrafluoroethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(4-chlorophenyl)-6-(2-(4-(1,1,2,2-tetrafluoroethoxy) benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)—N—(6-chloropyridin-3-yl)-6-(2-(4-(1 ,1,2,2-tetrafluoroethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(6-chloropyridin-3-yl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; N-(6-chloropyridin-3-yl)-4-(2,6-difluorophenyl)-6-(2-(4-(1,1,2,2-tetrafluoroethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; N-(6-chloropyridin-3-yl)-4-(2,6-dichlorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(4-chlorophenyl)-6-(2-(4-ethylbenzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-((2-(4-(2-chloro-6-fluorophenyl)-6-((4-chlorophenypamino)-1,3,5-triazin-2-yl)hydrazono)methyl)benzonitrile; 4-(2-butylidenehydrazinyl)-6-(2-chloro-6-fluorophenyl)-N-(4-chlorophenyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(4-chlorophenyl)-6-(2-(2-phenylethylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(4-chlorophenyl)-6-(2-(1-(4-(trifluoromethoxy)phenyl)ethylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-((6-chloropyridin-3-yl)methyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(p-tolyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(2-morpholinoethyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 2-(2-chloro-6-fluorophenyl)-4-(2,2-dimethylhydrazinyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazine; N—(3 -chloro-4-fluorophenyl)-4-(2-chloro-6-fluorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(4-fluoro-3-(trifluoromethyl)phenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-(4-(2-chloro-1,1,2-trifluoroethoxy)benzylidene)hydrazinyl)-6-(2-chloro-6-fluorophenyl)-N-(6-chloropyridin-3-yl)-1,3,5-triazin-2-amine; 4-(2-(4-(2-chloro-1,1,2-trifluoroethoxy)benzylidene)hydrazinyl)-6-(2-chloro-6-fluorophenyl)-N-(4-chlorophenyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(3,4-dichlorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(3,5-dichlorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(2-chlorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-tiazin-2-amine; N-(6-chloropyridin-3-yl)-4-(2-fluorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-methyl-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; N-(4-chlorophenyl)-4-(2-fluorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5triazin-2-amine; 4-(2-(2-chloro-6-fluorobenzylidene)hydrazinyl)-N-(4-chlorophenyl)-6-(4-(trifluoromethoxy)phenyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(6-chloropyridin-3-yl)-6-(2-(4-(trifluoromethyl)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(6-chloropyridin-3-yl)-6-(2-(4-methylbenzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(6-chloropyridin-3-yl)-6-(2-(4-methoxybenzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(6-chloropyridin-3-yl)-6-(2-(3-fluoro-4-(trifluoromethyl)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(4-chlorobenzyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; N-(4-chlorophenyl)-4-(2,6-dichlorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; N-(4-chlorophenyl)-4-(3-fluorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; N-(4-chlorophenyl)-4-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-6-(4-(trifluoromethoxy)phenyl)-1,3,5-triazin-2-amine; 4-(2,6-difluorophenyl)-N-(4-fluoro-3 -(trifluoromethyl)phenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2,6-difluorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-N-(4-(trifluoromethoxy)phenyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(2-chloropyridin-4-yl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine; 4-(2-chloro-6-fluorophenyl)-N-(5-chloropyridin-2-yl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine.
16. An insecticidal composition, comprising the compounds of Formula I,
wherein:
Y is N
Z is -aryl, —C 1 -C 8 alkylaryl,
X, is —H, —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, —NR i R j or —C 1 -C 8 alkylNR i R j ;
R 2 and R 3 are independently —H or —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, and —C 1 -C 8 alkylNR i R j , but R 2 and R 3 are not both H;
R i and R j are independently —H, or —C 1 -C 8 alkyl;
wherein heterocyclic is a 5-10 member cyclic or bicyclic aromatic or saturated —C 1 -C 8 cycloaliphatic ring moiety containing 1, 2, or 3 heteroatoms selected from N, O, or S;
wherein aryl, —C 3 -C 8 cycloalkyl and heterocyclic are optionally independently substituted with one to five substituents independently selected from -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl; and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN or —OH and a phytologically-acceptable carrier.
17. A compound of claim 10 wherein
R 2 is —H;
R 3 is optionally substituted —C 1 -C 6 alkyl, or optionally substituted -aryl;
X is an optionally substituted -aryl, C 1 -C 6 alkyl aryl, 6 member heterocyclic, C 1 -C 6 alkyl 6 member heterocyclic;
Z is optionally substituted aryl; and
aryl is an optionally substituted phenyl.
18. A compound of claim 17 wherein
wherein the phenyl is optionally substituted with 1-3 R 10 at any of the positions of any of the formula below;
R 10 is optionally independently selected from -halo, —CN, —OH, —C 1 -C 6 alkyl, or —O—C 1 -C 6 alkyl, and
at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN or —OH.
19. A compound of claim 18 wherein
the phenyl is optionally substituted with 1-3 R 10 ;
R 10 is optionally independently selected from -halo, —CN, —OH, C 1 -C 6 alkyl, or —O—C 1 -C 6 alkyl, at each occurrence and each R 10 alkyl may be optionally independently substituted with one to five halo, —CN, —OH, or —OCH 3 ; and
X is an optionally substituted -phenyl, C 1 -C 3 alkyl phenyl, 6 member heterocyclic with one or two heteroatoms, C 1 -C 3 alkyl 6 member heterocyclic with one or two heteroatoms.
20. A compound of claim 19 wherein phenyl is optionally substituted with 1-2 R 10 , and R 10 , is -halo, —OH, —CN, —OH, —C 1 -C 6 alkyl, or optionally independently substituted —O—C 1 -C 3 alkyl, wherein —O—C 1 -C 3 alkyl is optionally substituted with 1-5 halo, at any of the positions of any of the formula below
X is an optionally substituted -phenyl, C 1 -C 3 alkyl phenyl, 6 member heterocyclic with one heteroatom, or a C 1 -C 3 alkyl 6 member heterocyclic with one heteroatom.
21. A compound of claim 20 wherein
phenyl is optionally substituted with 1-2 R 10 , at any of the positions of any of the formula below
wherein X is either optionally substituted phenyl, or an optionally substituted pyridine wherein the optional substituent is selected from halo.
22. A compound of claim 21 wherein
phenyl is optionally substituted with 1-2 R 10 , and R 10 is halo, at any of the positions of any of the formula below
23. A compound of claim 22 wherein
Z is phenyl,
R 2 is —H, and
R 3 is phenyl.
24. A compound of claim 21 wherein
Z is phenyl optionally substituted with 1 R 10 , wherein R 10 is halo, —OH, —CN, or optionally substituted —O—C 1 -C 3 alkyl, at the position of the formula below
25. A compound of claim 24 wherein R 10 is —OH, —OCHF 2 , —OCF 3 , —OCHCl 2 , or —OCCl 3 .
26. A compound of claim 25 wherein R 10 is OCF 3 .
27. A compound of claim 21 wherein
R 3 is phenyl, optionally substituted with 1 R 10 , wherein R 10 is halo, —OH, —CN or optionally substituted —O—C 1 -C 3 alkyl, at the position of the formula below
28. A compound of claim 27 wherein R 10 is —OH, —OCHF 2 , —OCF 3 , —OCHCl 2 , or —OCCl 3 .
29. A compound of claim 26 wherein R 10 is OCF 3 .
30. An insecticial composition, comprising a compound of Formula I,
wherein:
Y is N
Z is -aryl, —C 1 -C 8 alkylaryl,
X, is —H, —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, —NR i R j or —C 1 -C 8 alkylNR i R j ;
R 2 and R 3 are independently —H or —C 1 -C 8 alkyl, -aryl, —C 1 -C 8 alkylaryl, —C 3 -C 8 cycloalkyl, —C 1 -C 8 alkylC 3 -C 8 cycloalkyl, heterocyclic, —C 1 -C 8 alkylheterocyclic, and —C 1 -C 8 alkylNR i R j , but R 2 and R 3 are not both H;
R i and R j are independently —H, or —C 1 -C 8 alkyl;
wherein heterocyclic is a 5-10 member cyclic or bicyclic aromatic or saturated —C 1 -C 8 cycloaliphatic ring moiety containing 1, 2, or 3 heteroatoms selected from N, O, or S;
wherein aryl, —C 3 -C 8 cycloalkyl and heterocyclic are optionally independently substituted with one to five substituents independently selected from -halo, —CN, —OH, —OCH 2 CH═CHCl, —C 1 -C 6 alkyl, —O—C 1 -C 6 alkyl, or —S—C 1 -C 6 alkyl; and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN or —OH, and a phytologically-acceptable carrier.
31. The application of the insecticidal composition of claim 30 applied to the locus of an insect selected from any of the following insect orders: Lepidoptera, Coleoptera, Diptera, Hymenoptera, Isoptera, Orthoptera, and Homoptera.
32. The application of claim 31 as applied to the locus of an insect selected from the order Lepidoptera.
33. The application of claim 31 as applied to the locus of an insect selected from the order Coleoptera.
34. The application of claim 31 as applied to the locus of an insect selected from the order Hymenoptera.
35. An insecticidal composition of claim 16 wherein said composition in the form of a spray, topical treatment, gel, seed coating, microcapsulation, bait, eartag, boluse, fogger, fumigant, aerosol or dust.