Structure-activity relationship development of dihaloaryl triazole compounds as insecticides and acaricides. 1. Phenyl thiophen-2-yl triazoles.
An extended lipophilic system that incorporated some key elements of first-generation 2,6-dihaloaryl actives, such as 1, demonstrated desirable efficacy against chewing insects as well as sap-feeding insects. These four-ring systems, based on 2, were accessed primarily via Suzuki couplings of halothiophene derivatives with appropriately substituted boronic acids. In particular, phenylthiophene systems that incorporated haloxyether groups, such as those in 3, 4, and 5, had the broadest spectrum of activity across chewing and sap-feeding insect pests. Expansion of this structure-activity relationship to include compounds with differing substitution patterns on the thiophene-C-ring and aryl-D-rings was undertaken. The synthesis and insecticidal activity of 3-aryl-5-(thiophen-2-yl)-1-methyl-1H-[1,2,4]triazoles will be described.
Cudworth
Denise P
DP
Dow AgroSciences LLC, 9330 Zionsville Road, Indianapolis, Indiana 46268, USA. dpcudworth@dow.com
Hegde
Vidyadhar B
VB
Yap
Maurice C H
MC
Guenthenspberger
Katherine A
KA
Hamilton
Christopher T
CT
Pechacek
James T
JT
Johnson
Peter L
PL
Bis
Scott J
SJ
Tisdell
F Eugene
FE
Dripps
James E
JE
Bruce
Timothy J
TJ
Dintenfass
Leonard P
LP
Gifford
James M
JM
Karr
Laura L
LL
Kempe
Margaret K
MK
McCormick
D'Lee C
DC
Schoonover
Joseph R
JR
D000053:Acari; D000818:Animals; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
D007306:Insecticides; D013876:Thiophenes; D014230:Triazoles