Plant protecting and regulating compositions – Plant growth regulating compositions – Stunting or dwarfing agent
Patent
1995-04-24
1997-05-20
Ivy, C. Warren
Plant protecting and regulating compositions
Plant growth regulating compositions
Stunting or dwarfing agent
504298, 549467, 549469, A01N 4312, A01N 3510, C07L30778
Patent
active
056312083
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/KR93/00069 filed Aug. 6, 1993.
BACKGROUND OF THE INVENTION
1. Technical Field
The present invention relates to novel cyclohexane-1,3-dione derivatives of the following formula (I) useful as herbicides and plant-growth regulants. ##STR2## wherein, X is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkoxy, halogen, C.sub.1 -C.sub.6 haloalkyl, nitro, cyano, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, sulfamoyl, N-(C.sub.1 -C.sub.6 alkyl) sulfamoyl and N,N-di(C.sub.1 -C.sub.6 alkyl) sulfamoyl group; on benzene ring, where n is 1, 2 or 3.
Also, cyclohexyl moiety, one of the substituents on benzofuran ring, is substituted at 4, 5, 6 or 7 position. The (X)n can't be filled only with hydrogens and the (X)n can substitute position where cyclohexyl moiety is not substituted; and C.sub.2 -C.sub.6 alkynyl group; haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, benzyl and C.sub.2 -C.sub.6 haloalkanoyl group; metal cation, C.sub.1 -C.sub.4 alkanoyl, C.sub.1 -C.sub.4 haloalkanoyl and benzoyl group.
2. Description of the Related Art
Cyclohexane-1,3-dione derivatives and their herbicidal activity were already known in the art. For example, Alloxidim-sodium (Australian Patent No. 464,655; United Kingdom Patent No. 1,461,170; U.S. Pat. No. 3,950,420) and Sethoxydim (Germany Patent No. 2,822,304) have come into the market as grass herbicides. Cyclohexane-1,3-dione derivatives having phenyl substituent (U.S. Pat. No. 4,511,391, U.S. Pat. No. 4,639,267 and U.S. Pat. No. 4,652,303) which have similar structure to our invention has been known. This present invention differs from the compounds having 2,3-dihydrobenzofurans disclosed in U.S. Pat. No. 4,511,391, in which 2-position of benzofurans were claimed only as methylene group.
In addition, the benzofuran moieties in the present invention can not be synthesized by the methods of the synthesis of the benzofurans disclosed in U.S. Pat. No. 4,511,391. The compounds in the present invention showed good rice tolerance, while the compound in the U.S. Pat. No. 4,511,391 showed not.
Furthermore a part of compounds developed by these inventors similar to the above formula (I) but differ in substituent of (X)n on benzene ring.
Therefore, with consideration as to the aforesaid points the present inventors have made efforts to develop new herbicidal compounds which have powerful herbicidal activity and good selectivity, especially useful for selective control barnyardgrass species in upland and paddy rice.
SUMMARY OF THE INVENTION
The object of the present invention is provide novel compounds of formular (I) and its preparation processes with strong herbicidal activities, useful as selective herbicides, especially for Gramineae grasses.
Another object is to provide herbicidal composition containing a compound of formula (I) as active ingredient.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is identified as cyclohexane-1,3-dione derivatives of the following formula (I), and agricultural preparations containing compounds of the formula (I) as an active ingredient. ##STR3## wherein, X, (X)n, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are respectively defined as described above.
In the formula (I) according to the present invention the preferred compounds are as follows: X is selected from the group consisting of hydrogen, halogen and C.sub.1 -C.sub.6 alkyl group, (X)n represents number of X substituents on benzene ring where n is 1, 2 or 3; R.sup.1 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.6 alkyl group; R.sup.2 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl group; R.sup.3 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl and C.sub.2 -C.sub.6 haloalkenyl; R.sup.4 is hydrogen.
Among above compounds, more preferred derivatives are as follows: R.sup.1 is selected from the group cons
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Kim Hyoung R.
Kim Jae N.
Kim Jin S.
Kim Kyoung M.
Ryu Eung K.
Covington Raymond
Ivy C. Warren
Korea Research Institute of Chemical Technology
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