Herbicidal oxabicycloalkane ethers

Chemistry: fertilizers – Processes and products – Forms or conditioning


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546141, 546142, 546153, 546155, 546158, 518460, 549 9, 549 23, 549 52, 549 54, 549 55, 549 56, 549 88, 549332, 549345, 549354, 549397, 549399, 549400, 549401, 549463, 549510, 549511, A01N 4308, C07D49308






1. Field of the Invention
The present invention relates to novel bicyclo ether derivative compounds, to compositions containing these ether derivative compounds, and to methods of using these compounds or compositions to control the growth of undesired vegetation.
2. Description of Related Art
Vieira et al., Helvetica Chimica Acta, 65(6) (1982), pp. 1700-06, teach the preparation of the oxabicyclic cyanohydrin acetates via a Diels-Alder reaction. ##STR1##
Vieria et al., Helvetica Chimica Acta, 66(6) (1983), pp. 1865-71 teach a chiral variant of the above described reaction which produces oxabicyclic cyanohydrin esters homologous to those depicted above, but with a (-)-camphanoyl group instead of an acetate group.
Black et al., Helvetica Chimica Acta, 67 (1984), pp. 1612-15, disclose a method for the preparation of the chiral oxabicyclic ketone via diastereoselective formation of a brucine complex of the corresponding cyanohydrin acetate. ##STR2##
Payne et al., U.S. Pat. No. 4,567,283 and Payne et al., U.S. Pat. No. 4,670,041 disclose a variety of herbicidal bicyclic ethers of the Formula ##STR3## wherein W is an unsaturated, aromatic or heterocyclic group. This reference also disclosed certain bicyclic and monocyclic intermediates to these compounds.
Payne et al., U.S. Pat. No. 4,525,203, disclose herbicidal bicyclic ethers of the Formula ##STR4##
GB 2188-931 discloses compounds of the following formula as herbicides: ##STR5##


This invention pertains to compounds of Formula I including stereoisomers, suitable agricultural compositions containing them and their use as broad spectrum preemergent and postemergent herbicides. ##STR6## wherein: X is (CH.sub.2).sub.m ; -C.sub.4 alkynyl, phenyl or C.sub.1 -C.sub.4 alkyl substituted by halogen, Ph, OH, CN, OR.sub.a, SO.sub.2 R.sub.a, PhSO.sub.2, N.sub.3, CO.sub.2 R.sub.a, or CO.sub.2 H; carbocyclic ring; ##STR7## Z.sup.1 is CH.sub.2, NR.sub.3, O, S or may be taken to form a double bond with an adjacent carbon; q.sup.1 is O then Z.sup.1 is CH.sub.2.
Preferred for either their biological activity or ease of synthesis are: -C.sub.3 alkynyl, or C.sub.1 -C.sub.2 alkyl substituted by OH, CN, OCH.sub.3, SO.sub.2 CH.sub.3, SO.sub.2 Ph or CO.sub.2 CH.sub.3 ; and
2. Compounds of Preferred 1 wherein;
3. Compounds of Preferred 1 wherein;
4. Compounds of Preferred 1 wherein;
5. Compounds of Preferred 2, 3 or 4 wherein;
6. Compounds of Preferred 2, 3 or 4 wherein;
7. Compounds of Preferred 2, 3 or 4 wherein;
8. Compounds of Preferred 2, 3 or 4 wherein;
9. Compounds of Preferred 2, 3 or 4wherein; ##STR8##
Specifically preferred are: o((2.2.1))heptane; and .


The compounds of Formula I exhibit geometrical and optical isomerism and may be prepared in geometrically or optically pure or mixed forms. The various individual optical and geometrical forms and various combinations thereof of the materials of the invention usually have some difference in herbicidal properties. Generally preferred for herbicidal efficacy are 1) those geometrical isomers of Formula I wherein the OW group resides on the same face of the carbocyclic ring as the O-Y bridge and 2) those optical isomers with the absolute configuration depicted in Formula Ia. The present invention contemplates all of the herbicidally active forms resulting from synthesis and from deliberately created mixtures. ##STR9##
The compounds of Formula Ia may be synthesized according to the well known Williamson Ether Synthesis (see N. Baggett in Comprehensive Organic Chemistry, D. Barton and W. D. Ollis eds., Vol. 1, pp. 819-832, Pergamon Press, New York (1979)) as shown in Scheme I by allowing bicyclic alcohols of Formula IV to react with appropriate alkylating agents represented as W-L where W represents those organic radicals defined previously and LG represents leaving group moieties such as chloride, bromide, iodide, and sulfonate esters. This is outlined in Scheme I. ##STR10##
The bicyclic alcohols of Formula IV are known in the art (U.

patent: 4388104 (1983-06-01), Powell et al.
patent: 4525203 (1985-06-01), Payne et al.
patent: 4554365 (1985-11-01), Mulder
patent: 4588821 (1986-05-01), Powell et al.


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