Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Patent
1996-04-01
1997-05-20
Davis, Zinna Northington
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
504133, 504136, 504138, 504139, 544211, 544336, 544242, 546309, 548136, 548205, 548235, 548561, 5483351, 5483355, 5483164, C07D21316, A01N 4340
Patent
active
056312067
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/US94/10342 filed Sep. 12, 1994.
This invention relates to certain heteroaryl substituted anilides which are useful as herbicides and their agriculturally suitable compositions as well as methods for their use as general or selective preemergent or postemergent herbicides or as plant growth regulants.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. Them are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
WO93/11097 discloses herbicidal anilide derivatives wherein an optionally substituted phenyl group occupies the ortho-position. In contrast, the compounds of the present invention bear a heteroaromatic group at that location and are therefore not disclosed therein.
SUMMARY OF THE INVENTION
The invention comprises compounds of Formula I: ##STR2## X is a single bond; O; S; or NR.sup.4 ; Y is O; S; or NCH.sub.3 ; -C.sub.2 alkoxy, OH, 1-3 halogens, or C.sub.1 -C.sub.2 alkylthio; CH2(C.sub.3 -C.sub.4 cycloalkyl); C.sub.3 -C.sub.4 cycloalkyl optionally substituted with 1-3 methyl groups; C.sub.2 -C.sub.4 alkenyl; C.sub.2 -C.sub.4 haloalkenyl; or optionally substituted phenyl; alkoxy; C.sub.1 -C.sub.2 alkylthio; C.sub.2 -C.sub.3 alkoxyalkyl; C.sub.2 -C.sub.3 alkylthioalkyl; cyano; nitro; NH(C.sub.1 -C.sub.2 alkyl); or N(C.sub.1 -C.sub.2 alkyl).sub.2 ; -C.sub.4 haloalkylthio; halogen; cyano; nitro; or methylthio; thereof. activity and/or ease of synthesis are:
1. Compounds of Formula I wherein: 1-3 halogens; C.sub.2 -C.sub.4 alkenyl; or C.sub.2 -C.sub.4 haloalkenyl; alkoxy; cyano; nitro; NH(C.sub.1 -C.sub.2 alkyl); or N(C.sub.1 -C.sub.2 alkyl).sub.2.
2. Compounds of Preferred 1 wherein: -C.sub.2 haloalkylthio; chlorine or bromine.
3. Compounds of Preferred 2 wherein: synthesis are: 2-methyl-N-[4-methyl-2-[6-(trifluoromethyl)-2-pyridinyl]phenyl]-propanamid e; and anamide.
Further embodiments of the invention include:
A composition for controlling growth of undesired vegetation comprising a herbicidally effective mount of a compound of Formula I as defined herein and at least one of a surfactant, solid or liquid diluent.
A method of controlling the growth of undesired vegetation comprising applying to the locus to be protected a herbicidally effective amount of the composition described above.
DETAILED DESCRIPTION OF THE INVENTION
Compounds of General Formula I can be readily prepared by one skilled in the art by using the reactions and techniques described in Schemes 1-7 of this section as well as by following the specific procedures given in Examples 1-13. The definitions of Q, X, Y, Z and R.sup.1 -R.sup.4 are as described in the Summary of the Invention.
Scheme 1 illustrates the preparation of compounds of Formula I whereby substituted phenyl compounds of Formula IIa wherein X.sup.2 is triakyltin (e.g., Me.sub.3 Sn), triakylsilyl (e.g., Me.sub.3 Si), or a boronic acid derivative (e.g., B(OH).sub.2) are coupled with heterocycles of Formula Ilia wherein X.sup.1 is chlorine, bromine, iodine or trifluoromethylsulfonyloxy (OTf). The coupling is carried out by methods known in the art: for example, see Tsuji, J., Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin (1980); Negishi, E., Acc. Chem. Res. (1982), 15, 340; Stille, J. K., Angew. Chem. (1986), 98, 504; Yamamoto, A. and Yamagi, A., Chem. Pharm. Bull. (1982), 30, 1731 and 2003; Dondoni et at., Synthesis (1987), 185;
Davis Zinna Northington
E. I. Du Pont de Nemours and Company
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