Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1993-05-21
1995-02-14
Bernhardt, Emily
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544283, 544285, 544286, 544287, 544288, 544289, A01N 4354, C07D23972, C07D23980, C07D23988
Patent
active
053896009
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention relates to certain substituted fused heterocyclic compounds 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. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
EP-A-353,902 discloses herbicidal compounds of the formula ##STR2## wherein, inter alia G and G.sup.1 are N and C; and
Ind. J. Chem. 1980, 19 B, 1011-1013 discloses without teaching herbicidal utility compounds of the formula ##STR3## only one of X, Y, or Z can be N; otherwise CH.
SUMMARY OF THE INVENTION
This invention comprises compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergence and/or postemergence herbicides or plant growth regulants. ##STR4## wherein X is N or CH; alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.3 alkylamino or N (C.sub.1 -C.sub.3 alkyl) (C.sub.1 -C.sub.3 alkyl); C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy; C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 halocycloalkyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 haloalkynyl, OR.sup.6, S(O).sub.n R.sup.7 or CN; halogen; C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 haloalkynyl, OR.sup.6, S(O).sub.n R.sup.7 or halogen; -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 haloalkenyl or C.sub.2 -C.sub.4 haloalkynyl; halogen; and that:
In the above definitions, the term "alkyl" used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.
"Alkoxy", "alkenyl" and "alkynyl" analogously also includes straight chain or branched isomers.
"Halogen", either alone or in compound words such as "haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples include CF.sub.3, CH.sub.2 CF.sub.3, CH.sub.2 CH.sub.2 F, CF.sub.2 CF.sub.3 and CH.sub.2 CHFCl.
Preferred for reasons including ease of synthesis and/or greater herbicidal efficacy are: S(O).sub.n.sup.R.sup.7 or CN; alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylamino and N (C.sub.1 -C.sub.2 alkyl) (C.sub.1 -C.sub.2 alkyl); haloalkyl, C.sub.2 -C.sub.3 haloalkenyl.
Specifically Preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are: otriazine 1-oxide; otriazine; and
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 1-10 and Equations 1-5 of this section as well as by following the specific procedures given in Examples 1-7.
Scheme 1 illustrates the preparation of compounds of General Formula I (where R, R.sup.1, R.sup.2, R.sup.3 X, Y, Z, and Q are defined as above) whereby heterocycles of Formula II where G is bromine or iodine can be coupled with substituted aryl compounds of Formula III where J is a trialkyltin (e.
REFERENCES:
patent: 3291757 (1966-12-01), Sturm et al.
patent: 3453365 (1969-07-01), Lane et al.
patent: 3900473 (1975-08-01), Diel et al.
patent: 5110347 (1992-05-01), Selby
Gogte et al., "Synthesis of Heterocyclic Compounds: Part XXII-Synthesis of 1,5-1,6-and 1,8-Naphthyridines", Indian Journal of Chemistry, 19B, 1011-1013, 1980.
Baker et al, J. Med. Chem. 15 pp. 235-237 (1972).
Bernhardt Emily
E. I. Du Pont de Nemours and Company
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