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US 5,294,622 AGranted
Substituted quinolines and cinnolines
AssigneeDowElanco
InventorsBarry A. Dreikorn, Glen P. Jourdan, Robert G. Suhr
Life of this patent
Estimating the term…
Abstract
The compounds of the formula: ##STR1## where the substituents are herein below defined, are fungicides, insecticides, and miticides.
Claims18
A compound of the formula ( 1) ##STR11## wherein:
- R.sup.1 to R.sup.4 are independently
- H, halo, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, halo (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, NO.sub.2, or NH.sub.2, at least two of R.sup.1 to R.sup.4 being H,
- W is CR.sup.5 ;
- R.sup.5 is H, CH.sub.3, or Cl,:
- R.sup.6 is H, CH.sub.3, Cl, or Br;
- A is --O--(CH.sub.2).sub.2 --Ar, --NR.sup.7 --(CH.sub.2).sub.2 --Ar, or --CR.sup.8 R.sup.9 --(CH.sub.2).sub.2 --Ar;
- R.sup.7 is H, (C.sub.1 -C.sub.4) alkyl, or acetyl;
- R.sup.8 and R.sup.9 are independently H, (C.sub.1 -C.sub.4) alkyl, halo, or OH, or R.sup.8 and R.sup.9 combine to form a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms;
- and
- Ar is
- 1. 3-benzodioxolyl
- fluorenyl,
- pyridyl,
- substituted pyridyl,
- indolyl,
- furanyl,
- substituted furanyl,
- thienyl, optionally substituted with CH.sub.3 or Cl,
- thiazolyl,
- cyclopentyl,
- 1-methylcyclopentyl,
- cyclohexenyl (tetrahydrophenyl),
- cyclohexyl (hexahydrophenyl),
- naphthyl,
- substituted naphthyl,
- dihydronaphthyl,
- tetrahydronaphthyl,
- decahydronaphthyl, or
- a group of formula (2):
- ##STR12## where R.sup.10 to R.sup.14 are independently H, halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, phenyl, substituted phenyl, NO.sub.2, NH.sub.2, acetoxy, OH, CN, SiR.sup.15 R.sup.16 R.sup.17, or OSiR.sup.15 R.sup.16 R.sup.17, where R.sup.15, R.sup.16, and R.sup.17 are independently (C.sub.1 -C.sub.4) alkyl or (C.sub.3 -C.sub.4) branched alkyl, phenyl, or substituted phenyl, provided that unless each of R.sup.10 to R.sup.14 is F or CH.sub.3, then at least two of R.sup.10 to R.sup.14 are H;
- or an acid addition salt of a compound of formula (1) or an N-oxide of a compound of formula (1) when W is CR.sup.5
- where, in the foregoing definitions, the term substituted phenyl refers to phenyl substituted with up to three groups selected from halo (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzyloxy;
- the term substituted phenoxy refers to a phenoxy group substituted with up to three groups selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN (C.sub.1 -C.sub.4) alkanoyloxy, or benzyloxy;
- the term substituted phenylthio refers to a phenylthio group substituted with up to three groups selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN (C.sub.1 -C.sub.4) alkanoyloxy, or benzyloxy;
- the term substituted phenylsulfonyl refers to a phenylsulfonyl group substituted with up to three groups selected from halo (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN (C.sub.1 -C.sub.4) alkanoyloxy, or benzyloxy;
- and
- the terms substituted naphthyl, substituted pyridyl, and substituted furanyl refer to these ring systems substituted with halo, halo (C.sub.1 -C.sub.4), CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, (C.sub.3 -C.sub.4) branched alkyl, phenyl, (C.sub.1 -C.sub.4) alkoxy, or halo (C.sub.1 -C.sub.4) alkoxy;
- provided that if A is NR.sup.7 --(CH.sub.2).sub.2 --Ar then Ar is a group of formula (2) wherein four of R.sup.10 to R.sup.14 are H and one of R.sup.10 to R.sup.14 is Cl, (C.sub.1 -C.sub.4) alkyl, halo (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.6) alkyl, (C.sub.1 -C.sub.4) alkoxy, halo (C.sub.1 -C.sub.4) alkoxy, phenyl, substituted phenyl, phenoxy, or substituted phenoxy.
35 more elements
Dependencies are inferred from the claim text.