Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1998-09-14
2000-06-27
Shah, Mukund J.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504216, 544212, 544309, 544310, 544311, 544312, 548241, A01N 4354, A01N 4366, A01N 4380, C07D41310
Patent
active
060807024
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The present invention relates generally to weed control in agriculture, horticulture, and other fields where there is a desire to control unwanted plant growth. Particularly, the present invention relates to certain herbicidal 3-(benzisoxazol-7-yl and 1,2-(2H)-benzisoxazolidin-3-on-7-yl)-heterocycles and certain derivatives and novel intermediates thereof. More particularly, the present invention relates to certain herbicidal (benzisoxazol-7-yl and 1,2-(2H)-benzisoxazolidin-3-on-7-yl)-heterocycles wherein the heterocycle is a 2,4-(1H, 3H)-pyrimidinedione, a 4,5,6,7-tetrahydro-1H-isoindole-1,3-dione, or a 1,2,5,6-tetrahydro-1,3,5-triazine-2,6-dione.
U.S. Pat. No. 5,169,431 discloses herbicidal uracil derivatives of formula: ##STR2## wherein: R=alkyl; A and Y=H or halogen; and Z=methyl or amino.
U.S. Pat. No. 5,521,147 discloses herbicidal compounds of the formula: ##STR3## where D and E are independently H or alkyl and R is alkyl or amino.
SUMMARY OF THE INVENTION
It has now been discovered that certain 3-(benzisoxazol-7-yl and (2H)-benzisoxazolidin-3on-7-yl)-heterocycles where the heterocycle is a 2,4-(1H, 3H)pyrimidinedione, a 4,5,6,7-tetrahydro-1H-isoindole-1,3-dione, or a 1,2,5,6-tetrahydro-1,3,5-triazine-2,6-dione have good activity as both pre- and post-emergence herbicides, especially on weeds in crops such as wheat, corn, and soybeans. The compounds are also effective as general dessicants that are useful in total vegetation control. This invention also relates to novel intermediates which are useful for making the herbicidal compounds.
DETAILED DESCRIPTION OF THE INVENTION
The novel compounds of the present invention have the following generic structure: ##STR4## wherein A is ##STR5## U=(a) N and X is attached to U by a double bond or (b) NR and X is attached to U by a single bond; benzyl, phenyl, or cyanoalkyl; with one or more halogen or alkyl groups, alkoxycarbonyl, alkoxycarbonylalkoxy, benzyl, benzyloxy, or haloalkyl;
As used in this specification, the terms "alkyl," "alkenyl," "alkynyl," "haloalkyl," and "alkoxy" used alone or as part of a larger moiety, includes straight or branched carbon chains of 1 to 6 carbon atoms. "Halogen" refers to fluorine, bromine or chlorine. "THF" means tetrahydrofuran, "DMF" means N,N-dimethylformamide, and "DBU" means 1,8-diazabicyclo[5.4.0]undec-7-ene.
Preferred compounds of the present invention include those of formulae II and III: ##STR6## wherein: R=CH.sub.3, CH.sub.2 CH.sub.3, or CH(CH.sub.3).sub.2 ; R.sup.1 =CH.sub.3, CHF.sub.2, or NH.sub.2 ; R.sup.2 =CH.sub.3 or phenyl; Y=4-Cl, 4-Br, or 4-CN; Z=6-F, 6-Cl, or 6-H; and R.sup.3 =CH.sub.3 or CF.sub.3. Particularly preferred are compounds of formula II or III wherein: R=CH.sub.3, CH.sub.2 CH.sub.3, or CH(CH.sub.3).sub.2 ; R.sup.1 =CH.sub.3 or NH.sub.2 ; R.sup.2 =CH.sub.3 ; Y=4-Cl or 4-Br; Z=6-F or 6-H; and R.sup.3 =CH.sub.3 or CF.sub.3.
Certain intermediates of the present invention are novel. These include compounds of formulae IV and V: ##STR7## wherein: R, Y and Z are as defined above for formula I, II, or III, and S=NH.sub.2, NHCO.sub.2 -alkyl, or N.dbd.C.dbd.O.
Compounds of the present invention represented by formula II may be prepared as shown in Scheme I below. An appropriately substituted chlorophenylcarboxylic acid is nitrated to give nitrobenzoic acid A which may be converted to the benzamide C in two steps via the acid chloride B. C undergoes cyclization with DBU to the corresponding (2-alkyl-7-nitro-substituted)-1,2(2H)-benzisoxazolidin-3-one (D). Reduction of the nitro group of D with iron in acetic acid provides the amino intermediate E, as described below in Example 6. Alternatively, when Y or Z is Br (for the purpose of directing the nitration in step a), catalytic hydrogenation of the nitro group with 10% Pd/C causes concommitant removal of the Br. Halogen substituents may be optionally introduced by reacting E with an N-halo succinimide. Examples 2-5 provide details of these procedures.
The isocyanate group of F is then cyclized with 3-amino-4,4,4-trifluo
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Crawford Scott D.
Maravetz Lester L.
Theodoridis George
FMC Corporation
Rao Deepak R.
Shah Mukund J.
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