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US 5,182,397 AGranted
Aryloxyspiroalkylindolinone herbicides
AssigneeAmerican Cyanamid Company
InventorsMichael E. Condon, Gary M. Karp, Jeffrey H. Birk
Life of this patent
Estimating the term…
Abstract
There are provided aryloxy-1'-(substituted)-spiro[cycloalkane-1,3'-indolin]-2'-one compounds, their herbicidal use, particularly for the selective control of undesirable plant species in the presence of cereal crops such as rice and wheat, and a method for the preparation thereof.
Claims5
A process for the preparation of a compound having the structure of formula I ##STR16## wherein M is N or CX;
- X, Y and Z are each independently hydrogen, halogen, CN, NO.sub.2 or C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogens;
- W is hydrogen, halogen, CN, NO.sub.2, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 carboalkoxy or C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogens or OR.sub.1 groups with the proviso that at least two of W, X, Y and Z must be other than CN or NO.sub.2 ;
- n is an integer of 1, 2, 3, 4 or 5;
- R is C.sub.1 -C.sub.6 alkyl;
- and
- R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl
- which comprises reacting a compound having the structure of formula III ##STR17## wherein M, Y, Z and W are as described above with at least one molar equivalent of the chlorosulfonium salt of a C.sub.1 -C.sub.4 alkyl ester of methylthioacetic acid in the presence of at least 1 equivalent of a base and a non-protic solvent at a temperature range of about -78.degree. C. to -30.degree. C. to form a first intermediate, reacting said first intermediate with at least one additional equivalent of a base to form a second intermediate, heating said second intermediate in the presence of an acid and a non-protic solvent at a temperature range of greater than about 90.degree. C. to form an aryloxy-3-(methylthio)-2-indolinone, reacting said aryloxy-3-(methylthio)-2-indolinone with sufficient Raney Nickel in a suitable protic solvent to form the corresponding aryloxy-2-indolinone, reacting said aryloxy-2-indolinone with dialkylsulfate in the presence of an alkali metal hydride and a suitable solvent to form an aryloxy-1-alkyl-2-indolinone and reacting said aryloxy-1-alkyl-2-indolinone with a dihaloalkane of formula VI ##STR18## wherein m is an integer of n+1 in the presence of at least 2 equivalents of an alkali metal hydride and a polar solvent to give the compound of formula I.
4 more elements
A process for the preparation of a compound having the structure of formula I ##STR19## wherein M is N or CX;
- X, Y and Z are each independently hydrogen, halogen, CN, NO.sub.2 or C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogens;
- W is hydrogen, halogen, CN, NO.sub.2, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 carboalkoxy or C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogens or OR.sub.1 groups with the proviso that at least two of W, X, Y and Z must be other than CN or NO.sub.2 ;
- n is an integer of 1, 2, 3, 4 or 5;
- R is C.sub.1 -C.sub.6 alkyl;
- and
- R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl
- which comprises reacting a compound having the structure of formula IVa ##STR20## wherein M, Y, Z and W are as described above with a protecting agent to form a 1-protected-aryloxy-2-indolinone, reacting said protected indolinone with a dihaloalkane of formula VI ##STR21## wherein m is an integer of n+1 in the presence of at least 2 equivalents of an alkali metal hydride and a polar solvent to give a corresponding protected spiroalkylindolinone intermediate, reacting said spiroalkylindolinone with a deprotecting agent to give an unsubstituted aryloxyspiroalkylindolinone compound and reacting said unsubstituted aryloxyspiroalkylindolinone compound with a C.sub.1 -C.sub.6 alkyl halide in the presence of a base and a solvent to give said compound of formula I.
4 more elements
A process for the preparation of a compound having the structure of formula IX ##STR22## wherein M is N or CX;
- X, Y and Z are each independently hydrogen, halogen, CN, NO.sub.2 or C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogens;
- W is hydrogen, halogen, CN, NO.sub.2, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 carboalkoxy or C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogens or OR.sub.1 groups with the proviso that at least two of W, X, Y and Z must be other than CN or NO.sub.2 ;
- n is an integer of 1, 2, 3, 4 or 5;
- and
- R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl
- which comprises reacting a compound having the structure of formula IVa ##STR23## wherein M, Y, Z and W are as described above with a protecting agent to form a 1-protected-aryloxy-2-indolinone, reacting said protected indolinone with a dihaloalkane of formula VI ##STR24## wherein m is an integer of n+1 in the presence of at least 2 equivalents of an alkali metal hydride and a polar solvent to give a corresponding protected spiroalkylindolinone intermediate, and reacting said spiroalkylindolinone with a deprotecting agent to give said compound of formula IX.
3 more elements
Dependencies are inferred from the claim text.