This invention relates to certain herbicidal ethers, agriculturally suitable compositions thereof, and a method for their use as broad spectrum preemergent or postemergent herbicides.
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.
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##
WO91/03464 discloses bicyclic ethers such as: ##STR3## wherein inter alia X and Y are independently C(R.sup.3) (R.sup.4)OR.sup.5 ;
R.sup.5 is C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkenyl, C3-C.sub.4 alkynyl, CH.sub.2 -phenyl or C.sub.1 -C.sub.4 alkyl substituted with OR.sup.8 or OCF3; PA1 R.sup.2 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl; PA1 R.sup.3 and R.sup.4 are independently H, C.sub.1 -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 ; ##STR5## X is CR.sup.5 R.sup.6 Y.sup.1, CR.sup.5 .dbd.CR.sup.6 Y.sup.3 or R.sup.5 R.sup.6 PA1 R.sup.5 and R.sup.6 are independently H or C.sub.1 -C.sub.3 alkyl PA1 Y.sup.1 is H; C.sub.1 -C.sub.4 alkyl optionally substituted with Y.sup.2 ; C.sub.3 -C.sub.6 cycloalkyl; CN; C(O)NR.sup.7 R.sup.8 ; C(O) NHOR.sup.9 ; CO.sub.2 R.sup.10 ; C(O)R.sup.11 C(OR.sup.22) (OR.sup.23)R.sup.11 ; CHO; CH(OR.sup.22) (OR.sup.23); CH-NOR.sup.16 CR.sup.11 .dbd.NOR.sup.17 ; SR.sup.15 ; halogen; C.sub.2 -C.sub.4 alkenyl optionally substituted with 1-3 halogens, CO.sub.2 (C.sub.1 -C.sub.3 alkyl), CN or CHO; C.sub.2 -C.sub.4 alkynyl optionally substituted with halogen; S(O).sub.n R.sup.12 ; SO.sub.2 NR.sup.13 R.sup.14 ; NO.sub.2 N.sub.3 SCN; phenyl optionally substituted with 1-3 substituents selected from CH.sub.3, OCH.sub.3, SCH.sub.3, CF.sub.3 and halogen; imidazole; triazole; tetrazole; or ##STR6## Y.sup.2 is CN; C(O)NR.sup.7 R.sup.8 ; C(O)NHOR.sup.9 ; CO.sub.2 R.sup.10 ; C(O)R.sup.11 ; CHO; CH.dbd.NOR.sup.16 ; CR.sup.11 .dbd.NOR.sup.17 ; SR.sup.15 ; 1-3 halogens C.sub.2 -C.sub.4 alkenyl optionally substituted with 1-3 halogens; C.sub.2 -C.sub.4 alkynyl optionally substituted with halogen; S(O).sub.n R.sup.12 ; SO.sub.2 NR.sup.13 R.sup.14 ; NO.sub.2 ; N.sub.3 ; SCN; phenyl optionally substituted with 1-3 substituents selected from CH.sub.3, OCH.sub.3, SCH.sub.3, CF.sub.3 and halogen; imidazole triazole tetrazole or ##STR7## Y.sup.3 is H, C.sub.1 -C.sub.3 alkyl, CN, CO.sub.2 R.sup.10, C(O)R.sup.11, CHO or halogen; PA1 R.sup.7 R.sup.8 R.sup.13 and R.sup.14 are independently H or C.sub.1 -C.sub.3 alkyl; R.sup.7 and R.sup.8 may be taken together to form a 5- or 6-membered ring and R.sup.13 and R.sup.14 may be taken together to form a 5- or 6-membered ring; PA1 R.sup.9, R.sup.12, R.sup.16 and R.sup.17 are independently C.sub.1 -C.sub.3 alkyl; PA1 R.sup.10 is H; C.sub.1 -C.sub.6 alkyl optionally substituted with 1-3 halogens, OR.sup.18, CN or phenyl optionally substituted with 1-3 substituents selected from halogen, CH.sub.3 and OCH.sub.3 ; C.sub.3 -C4alkenyl; or C.sub.3 -C.sub.4 alkynyl; PA1 R.sup.11 is C.sub.1 -C.sub.6 alkyl optionally substituted with 1-3 halogens, OR.sup.18, CN or phenyl optionally substituted with 1-3 substituents selected from halogen, CH.sub.3 and OCH.sub.3 ; C.sub.2 -C.sub.4 alkenyl; C.sub.2 -C.sub.4 alkynyl; or phenyl optionally substituted with 1-3 substituents selected from halogen, CH.sub.3 and OCH.sub.3 ; PA1 R.sup.15 is H, C.sub.1 -C.sub.3 alkyl or benzyl; PA1 n is 1 or 2; PA1 Q is CH.sub.2 W or ##STR8## q and r are independently 0-2; R.sup.18 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sup.19 is H, halogen, C.sub.1 -C.sub.3 alkyl, OR.sup.20, SR.sup.20 or CN; PA1 R.sup.20 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl; PA1 Z is CH.sub.2, NR.sup.21, O, S or may be CH and taken to form a double bond with an adjacent carbon; PA1 R.sup.21 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sup.22 and R.sup.23 are independently C.sub.1 -C.sub.3 alkyl or may be taken together to from a 5- or 6-membered ring; PA1 R.sup.24, R.sup.25 and R.sup.26 are independently H or C.sub.1 -C.sub.2 alkyl; PA1 W is phenyl optionally substituted with 1-3 substituents selected from halogen, 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-, 6- or 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from the group 0-2 nitrogens, 0-2 oxygens and 0-2 sulfurs, each ring optionally substituted with 1-2 substituents selected from halogen, CH.sub.3 and OCH.sub.3 ; PA1 1) in compounds of Formulas I and II, Y.sup.1 is other than H, C.sub.1 -C.sub.4 alkyl or halogen, and Y.sup.2 is other than halogen(s); PA1 2) in compounds of Formula IV, when Q is other than CH.sub.2 W, then Y.sup.1 is other than H or C.sub.1 -C.sub.4 alkyl; PA1 3) the sum of q and r is 0-2; and PA1 4) if the sum of q and r is O then Z is CH.sub.2. PA1 1. Compounds of Formulae I, II, III or IV wherein: PA1 3. Compounds of Preferred 2 wherein: PA1 4. Compounds of Preferred 3 wherein: PA1 6. Compound of Preferred 5 wherein: PA1 7. Compounds of Preferred 6 wherein the compound is of Formula I. PA1 8. Compounds of Preferred 6 wherein the compound is of Formula II. PA1 9. Compounds of Preferred 6 wherein the compound is of Formula III. PA1 10. Compounds of Preferred 6 wherein the compound is of Formula IV. PA1 (2-endo, 4-endo )-(.+-.)-4-[(2,6-difluorophenyl)-methoxy]-5-methyl -6-oxa-bicyclo[3.2.1 ]octane-2-acetonitrile; (2-endo, 4-endo)-(.+-.)-5-ethyl-4-[(2-fluorophenyl) -methoxy ]-6-oxabicyclo[3.2.1]octane-2-acetonitrile PA1 (2-endo, 4-endo )-(.+-.)-5-ethyl-4-(phenylmethoxy)-6-oxabicyclo [3.2.1 ]octane-2-acetonitrile (2-endo, 4-endo)-(.+-.)-4-[(2,6-difluorophenyl)-methoxy]-5-ethyl-6-oxabicyclo [3.2.1 ]octane-2-acetonitrile PA1 (2-endo, 4-endo)-(.+-.)-5-ethyl-4-[(2-fluorophenyl)-methoxy]-5-methyl-6-oxabicyclo[ 3.2.1]octane-2 -acetonitrile; PA1 (2-endo, 4-endo)-(.+-.)-4-[(2-fluorophenyl)methoxy]-5-methyl-6-oxabicyclo[3.2.1]oct ane-2-acetonitrile; PA1 (2-endo, 4-endo )-(.+-.)-2-(bromomethyl)-5-methyl-4-(phenylmethoxy)-6-oxabicyclo[3.2.1]oct ane; PA1 (2-endo, 4-endo)-(.+-.)-5-ethyl-4-[(2-fluorophenyl) -methoxy]-2-(iodomethyl)-6-oxabicyclo[3.2.1]-octane; PA1 (2-endo, 4-endo)-(.+-.)-4-[(2-chlorophenyl)methoxy]-5-methyl-6-oxabicyclo[3.2.1]oct ane-2-acetonitrile; PA1 (2-endo, 4-endo)-(.+-.)-2-(iodomethyl)-5-methyl-4-(phenylmethoxy)-6-oxabicyclo[3.2. 1]octane; and PA1 (2-endo, 4-endo)-(.+-.)-5-ethyl-2-[(methylthio)methyl]-4-(phenylmethoxy)-6-oxabicyc lo[3.2.1]octane.
It is an object of the present invention to provide compounds and compositions which exhibit herbicidal activity on a variety of 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.