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N-Alkylaryltriazine Herbicides: A Possible Link Between Triazines and Phenylureas

Published online by Cambridge University Press:  12 June 2017

Gary Gardner ,
James R. Sanborn  and
John R. Goss
Gary Gardner
Affiliation:
Shell Agric. Chem. Co., Biol. Sci. Res. Ctr., Modesto, CA
James R. Sanborn
Affiliation:
Shell Agric. Chem. Co., Biol. Sci. Res. Ctr., Modesto, CA
John R. Goss
Affiliation:
Shell Agric. Chem. Co., Biol. Sci. Res. Ctr., Modesto, CA
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Abstract

A comparison of the structure of the α-methylbenzyl analogue (MBAT) of atrazine with the Photosystem II herbicides atrazine [6-chloro-N-ethyl-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine] and diuron [N′-(3,4-dichlorophenyl)-N,N-dimethylurea] suggested that N-alkylbenzyltriazines may be a structural bridge between the triazines and the phenylureas. In the phenylureas, the addition of chlorines at the meta and/or para positions produces a marked increase in activity. Chloro-substituted derivatives of MBAT were synthesized to determine whether this structure-activity relationship also applies to the alkylaryltriazines. Addition of a chlorine to MBAT at the 4-position (CMBAT) caused a substantial increase in intrinsic activity, and a second chlorine at the 3-position (DCMBAT) caused a further increase. In direct comparisons, DCMBAT was more active in vitro than terbuthylazine [6-chloro-N-ethyl-N′-(1,1-dimethylethyl)-1,3,5-triazine-2,4-diamine], the most active chlorotriazine, and was also more active than diruon. The effects of DCMBAT were also measured on triazine-resistant pigweed (Amaranthus hybridus L. # AMACH) both in vivo and in vitro. The activity of this compound in triazine-resistant chloroplasts was intermediate between that of atrazine and diruon both in inhibition of photosynthetic electron transport and in competition for diuron binding sites, with half-maximal values falling in the micromolar range. Whole plant phytotoxicity of DCMBAT on triazine-resistant pigweed was also intermediate between that of diuron and atrazine. Since DCMBAT is a triazine with biological properties similar to that of a urea, we conclude that in a functional as well as structural sense, DCMBAT is a herbicide that is a hybrid between a triazine and a urea.

Keywords

Photosystem IIelectron transportbindinginhibitoratrazineresistancediuronstructure-activityPisum sativumAmaranthus hybridusAmaranthus retroflexusAMACHAMARE
Type
Physiology, Chemistry, and Biochemistry
Information
Weed Science , Volume 35 , Issue 6 , November 1987 , pp. 763 - 769
Copyright
Copyright © 1987 by the Weed Science Society of America 

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References

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