Herbicidal oxabicyclo ethers

Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing

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504250, 504292, 544336, 546141, 546153, 546269, 548454, 549 23, 549 52, 549 60, 549399, 549401, 549414, 549463, A01N 4312, C07D30700

Patent

active

052349004

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to novel oxabicyclo 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. More particularly, the present invention relates to a variety of compounds, compositions, and methods of using them which are herbicidally active on a wide variety of weed species and exhibit safety to rice, cereals and broadleaf crops.


BACKGROUND OF THE INVENTION

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 ##STR1##
U.S. Pat. No. 4,798,621 and WO 8,902,219 both disclose bicyclic ethers and their method-of-use in rice.
U.S. Pat. No. 4,486,219 discloses bicyclic ethers of the formula: ##STR2##
It is an object of the present invention to provide compounds and compositions which exhibit herbicidal activity on a variety of economically important weed species. It is a further object of the present invention to provide compounds and compositions that are herbicidally safe to rice, cereals and broadleaf crops. It is a feature of the present invention to furnish novel oxabicyclo ethers that exhibit useful herbicidal activity. These and other objects, features and advantages will become apparent with respect to the following description of the invention.


SUMMARY OF THE INVENTION

The present invention comprises compounds of the formulas selected from the group consisting of: ##STR3## and stereoisomers thereof, wherein -C.sub.4 alkynyl, phenyl or C.sub.1 -C.sub.4 alkyl substituted by Ph, OH, CN, OR.sup.8, SO.sub.2 R.sup.8, PhSO.sub.2, N.sub.3, CO.sub.2 R.sup.8 or CO.sub.2 H; -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl or C.sub.1 -C.sub.3 alkyl substituted with OCH.sub.3 or OCH.sub.2 CH.sub.3 ; -C.sub.4 alkynyl, benzyl or C.sub.1 -C.sub.4 alkyl substituted with OR.sup.8, OCF.sub.3 ; ##STR4## W is phenyl optionally substituted with 1-3 substituents selected from F, Cl, Br, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, OH, CN, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 --C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.2 -C.sub.4 alkenyl and C.sub.2 -C.sub.4 alkynyl, or W is a 5 or 6-membered heterocyclic ring containing 0-2 nitrogens, 0-2 oxygens or 0-2 sulfurs, each ring optionally substituted with 1-2 substituents selected from F, Cl, Br, CH.sub.3 and OCH.sub.3 ; with an adjacent carbon; carbon atoms; Y is H;
A representative exemplification of the aforementioned heterocycles includes but is not limited to pyrrole, furan, thiophene, tetrahydropyran, tetrahydrofuran, isoxazole, oxazole, pyrazole, imidazole, thiazole, pyridine and pyrazines;
Preferred compounds of the invention for either their biological activity or ease of synthesis are:
1. Compounds of Formulas I, II, III, IV, V, VI, VII, or VIII wherein: Br, CH.sub.3 and OCH.sub.3 ; or W is tetrahydropyran, tetrahydrofuran, thiophene, isoxazole, pyridine or pyrazine, each ring optionally substituted with 1-2 substituents selected from F, Cl, Br, CH.sub.3 and OCH.sub.3 ; ##STR5## R.sub.a is H or C.sub.1 -C.sub.3 alkyl; and R.sup.5 is other than benzyl.
2. Compounds of Preferred 1 wherein R.sup.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.3 alkenyl or C.sub.2 -C.sub.3 alkynyl.
3. Compounds of Preferred 2 wherein -C.sub.4 alkynyl; -C.sub.4 alkynyl; -C.sub.4 alkynyl; -C.sub.4 alkynyl; -C.sub.4 alkynyl;
4. Compounds of Preferred 3 wherein Q is Q-1, Q-3, Q-6, Q-7 or Q-15.
5. Compounds of Preferred 4 wherein the compound is of Formula I.
6. Compounds of Preferred 4 wherein the compound is of Formula II.
7. Compounds of Preferred 4 wherein the compound is of Formula III.
8. Compounds of Preferred 4 wherein the compound is of Formula IV.
9. Compounds of Preferred 4 wherein the compound is of Formula V.
10. Compounds of Preferred 4 wherein the compound is of Formula VI.
11. The Compounds of Preferred 4 wherein the compound is of Formula VII.
12. Compounds of Preferred 4 wherein the com

REFERENCES:
patent: 4486219 (1984-12-01), Powell
patent: 4536586 (1985-08-01), Powell
patent: 4567283 (1986-01-01), Payne et al.
patent: 4670041 (1987-06-01), Payne et al.
patent: 4798621 (1989-01-01), Ackerson et al.

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