Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-11-22
1996-03-19
Ramsuer, Robert W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548359S, A01N 4390, C07D491048
Patent
active
055004385
DESCRIPTION:
BRIEF SUMMARY
The substituted anilides of this invention are unknown in the art, with WO 90/07495 being perhaps the most relevant publication in this regard. The anilides of this invention include all geometric and stereoisomers, arthropodicidally suitable salts thereof, arthropodicidal compositions containing them and their use to control arthropods in agronomic and nonagronomic environments. The term "compounds" includes all such isomers and salts thereof. The compounds are: ##STR3## wherein Q is selected from the group ##STR4## R.sup.1 is selected from the group Cl, Br, CF.sub.3, OCF.sub.3, OCF.sub.2 H and OSO.sub.2 CF.sub.3 ; R.sup.1 being OCF.sub.3 when Q is Q-3 and Y is CH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 or CH.sub.2 Ph; OCF.sub.2 H and OCH.sub.2 CF.sub.3 ; alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.1 -C.sub.3 alkylsulfonyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkylalkyl, NR.sup.6 R.sup.7, N.dbd.CR.sup.8 R.sup.9, OR.sup.6, COR.sup.4, CO.sub.2 R.sup.4 and C.sub.1 -C.sub.6 alkyl substituted by a group selected from halogen, C.sub.1 -C.sub.3 alkoxy, CN, NO.sub.2, S(O).sub.n R.sup.4, COR.sup.8, CO.sub.2 R.sup.8 and phenyl, the phenyl optionally substituted by a group selected from halogen, CN, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkyl and C.sub.1 -C.sub.2 haloalkoxy; Y being NR.sup.6 R.sup.7, N.dbd.CR.sup.8 R.sup.9 or OR.sup.6 when Q is Q-2; and Y being other than COR.sup.4 and CO.sub.2 R.sup.4 when Q is Q-3; 4-Cl-Ph and C.sub.1 -C.sub.3 alkyl; when Y is COR.sup.4 or CO.sub.2 R.sup.4, Q is Q-1 and Z.sup.1 is O; -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, SO.sub.2 NR.sup.8 R.sup.9 SO.sub.2 R.sup.10, COR.sup.8, CONR.sup.8 R.sup.9, CO.sub.2 R.sup.8, phenyl optionally substituted with halogen or C.sub.1 -C.sub.4 alkoxy, and benzyl optionally substituted with halogen; ; -C.sub.4 haloalkyl and phenyl optionally substituted by a group selected from halogen, CN, NO.sub.2, CF.sub.3 and OCF.sub.3 ; --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- and --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --; -C.sub.4 haloalkyl; being H when Q is Q-1 and Y is CH.sub.3 or C(O)CH.sub.3 ;
Preferred for reasons including greater arthropodicidal efficacy are: R.sup.9 or OR.sup.6 ; and
Specifically preferred is Compound E: 2-[[-1-[4(trifluoromethyl)phenyl]-hydrazino]carbonyl]-2,3-dihydro-7-(trifl uoromethyl)[ 1]benzopyrano[4,3-C]pyrazole-3a (4H) -carboxylate.
Specifically preferred are Compounds G: 2,3-dihydro-2-[[N-methyl-N-[4-(trifluoromethyl)phenyl]amino]carbonyl]-7-(t rifluoromethyl)[1]benzopyrano[4,3-c]pyrazole-3a(4H)-carboxylate, 7-chloro-2,3-dihydro-2-[[N-methyl-N-[4-(trifluoromethyl)phenyl]amino]carbo nyl][1]benzopyrano[4,3-c]pyrazole-3a(4H)-carboxylate, 2-[[N-(4-chlorophenyl)-N-methylamino]carbonyl]-2,3-dihydro-7-(trifluoromet hyl)-[1]benzopyrano[4,3-c]pyrazole-3a(4H)-carboxylate, 2-[[N-(4-bromophenyl)-N-methylamino]-carbonyl]2,3-dihydro-7-(trifluorometh yl)[1]benzopyrano[4,3-c]pyrazole-3a(4H)-carboxylate, and (trifluoromethoxy)-phenyl]amino]carbonyl]-7-(trifluoro-methyl)[1]benzopyra no[4,3-c]pyrazole-3a (4H)-carboxylate.
In the above definitions, the term "alkyl", used either alone or in compound words such as "haloalkyl" includes straight chain or branched alkyl such as methyl, ethyl, n-propyl, isopropyl, butyl, pentyl or the different hexyl isomers. Alkenyl includes straight chain or branched alkenes, such as 1-propenyl, 2-propenyl, 3-propenyl and the different hexenyl isomers. Alkynyl includes straight chain or branched chain alkynyl groups such as 1-pentynyl, 2-pentynyl, 3-pentynyl and the different hexynyl isomers. Alkoxy includes methoxy, ethoxy, n-propyloxy and isopropyloxy. The term "halogen", either alone or in compound words such as "haloalkyl", means fluorine, chlorine, bromine or iodine Further, when used in compound words such as "haloalkyl" said alkyl can be partially or fully substituted with halogen atoms, which can 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 CHFCl. The tota
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Barnette William E.
Harrison Charles R.
Lahm George P.
Piotrowski David W.
Wing Keith D.
E. I. Du Pont de Nemours and Company
Ramsuer Robert W.
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