Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-10-19
1995-08-22
Ramsuer, Robert W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548216, A61K 3142, C07D26312
Patent
active
054440793
DESCRIPTION:
BRIEF SUMMARY
This invention pertains to spirocyclic oxa- and thia-zolines as arthropodicides. EP 345,775 and EP 432,661 disclose non-spirocyclic oxa- and thia-zolines as insecticides.
SUMMARY OF THE INVENTION
The invention pertains to compounds of Formula I, including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use as arthropodicides in both agronomic and nonagronomic environments. The compounds are ##STR1## wherein A is selected from the group a direct bond, O, S, --XCH.sub.2 -- and C.sub.1 -C.sub.3 straight or branched chain alkylene; when A is --XCH.sub.2 --, the point of attachment to the phenyl ring is X or CH.sub.2 ; --Y(CH.sub.2).sub.m -- and C.sub.1 -C.sub.3 straight or branched chain alkylene; when G is --Y(CH.sub.2).sub.m --, the point of attachment to the phenyl ring is Y or the terminal carbon, and the ring containing A and G has 5-7 members; C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl and C.sub.1 -C.sub.6 haloalkoxy; C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.1 -C.sub.16 haloalkyl. C.sub.2 -C.sub.16 alkenyl, C.sub.2 -C.sub.16 haloalkenyl, C.sub.2 -C.sub.16 alkynyl, C.sub.2 -C.sub.16 haloalkynyl, C.sub.2 -C.sub.16 alkoxyalkoxy, OR.sup.5, R.sup.5 OC(O)--, R.sup.5 C(O)-- and ##STR2## W is selected from the group direct bond, S, O, C(.dbd.O), C(.dbd.O)O, C(.dbd.O)O--C.sub.1 -C.sub.2 alkylene, C.sub.1 -C.sub.4 alkylene, O--C.sub.1 -C.sub.4 alkylene and O--C.sub.2 -C.sub.4 alkenylene, wherein when W is O--C.sub.1 -C.sub.4 alkylene or O--C.sub.2 -C.sub.4 alkenylene, the oxygen atom can be attached to either aromatic ring and when W is C(.dbd.O)O or C(.dbd.O)O--C.sub.1 -C.sub.2, the C(.dbd.O) moiety can be attached to either aromatic ring; C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, C 1-C.sub.6 alkylthio, CN and NO.sub.2 ; -C.sub.16 cycloalkylalkyl, C.sub.1 -C.sub.16 alkyl, C.sub.1 -C.sub.16 haloalkyl, C.sub.2 -C.sub.16 alkenyl, C.sub.2 -C.sub.16 haloalkenyl, C.sub.2 -C.sub.16 alkynyl and C.sub.2 -C.sub.16 haloalkynyl; C.sub.1 -C.sub.10 alkoxy, C.sub.1 -C.sub.10 haloalkyl, C.sub.1 -C.sub.10 haloalkoxy and Si(R.sup.7)(R.sup.8)R.sup.9 ;
Preferred Compounds A are compounds of Formula I wherein: --Y--CH.sub.2 --, and --Y(CH.sub.2).sub.m --;
Specifically preferred for biological activity is the compound of Preferred A which is 'H)-oxazole].
Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers and geometric isomers. One skilled in the an will appreciate that one stereroisomer may be more active than the others and how to separate stereoisomers. Accordingly, the present invention comprises racemic mixtures, individual stereoisomers, and optically active mixtures of compounds of Formula I as well as their agriculturally suitable salts.
In the above recitations, the term "alkyl" used either alone or in compound word such as "alkylthio" or "haloalkyl", denotes straight or branched alkyl such as methyl, ethyl, n-propyl, isopropyl and the different butyl, pentyl and hexyl isomers. Similarly, the terms "alkylene" and "alkenylene" denote straight or branched chain groups.
Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. Alkenyl denotes straight or branched chain alkenes such as vinyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. Alkynyl denotes straight chain or branched alkynes such as ethynyl,1-propynyl, 3-propynyl and the different butynyl, pentynyl and hexynyl isomers. Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH.sub.2 CH.sub.2 F, CF.sub.2 CF.sub.3 and CH.sub.2
REFERENCES:
patent: 4544662 (1985-10-01), Brittain et al.
Dirlam, N. L. et al., "Novel Synthesis of the Aldose Reductase Sorbinil via Amidoalkylation, Intramolecular Oxazolidin-5-one Alkylation, and Chymotriypsin Resolution", J. Org. Chem., 52, 3587-3591 (1987).
Miyamoto, S. et al, Chemical Abstracts, 117(13), Sep. 28, 1992, Abstract No. 131181s.
Cross Laura R.
E. I. Du Pont de Nemours and Company
Ramsuer Robert W.
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