Quinazoline derivatives
First Claim
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1. A compound of the formula (1) ##STR13## wherein R1 to R4 are independently H, halo, (C1 -C4) alkyl, branched (C3 -C4) alkyl, halo (C1 -C4) alkyl, halo (C1 -C4) alkoxy, (C1 -C4) alkoxy, halo (C1 -C4) alkylthio, OH, CN, NO2, or NH2, at least two of R1 to R4 being H;
- Y is X--W--Ar,X is O, or NR7, or CR8 R9 ;
Z is H, Cl, OCH3, CH3, or CCl3 ;
R7 is H, (C1 -C4) alkyl, or acetyl;
R8 and R9 are independently H, (C1 -C4)alkyl, (C1 -C4) acyl, halo or OH, or R8 and R9 combine to form a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms;
W is an alkylene chain 2 to 8 carbon atoms long, that optionally includes a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms, and optionally is substituted with (C1 -C3) alkyl, (C2 -C4) alkenyl, phenyl, (C3 -C8) cycloalkyl, halo, hydroxy, or acetyl; and
Ar isimidazolyl,indolyl,thienyl, optionally substituted with CH3 or Cl,thiazolyl,
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Abstract
Substituted quinazolines of the formula (1): ##STR1## wherein: R1 to R4 are independently H, halo, (C1 -C4) alkyl, branched (C3 -C4) alkyl, halo (C1 -C4) alkyl, (C1 -C4) alkoxy, NO2, or NH2,
provided that
at least two of R1 to R4 are H;
Y is H, Cl, X--W--Ar, or O--Alk;
X is O, NR7, or CR8 R9 ;
Z is H, Cl, OCH3, CH3, or --NR7 --W--Ar, provided that Z can be --NR7 --W--Ar only if Y is H, Cl, or NR7 --W--Ar and Z must be --NR7 --W--Ar if Y is H or Cl, which are plant fungicides, miticides, and insecticides.
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Citations
63 Claims
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1. A compound of the formula (1) ##STR13## wherein R1 to R4 are independently H, halo, (C1 -C4) alkyl, branched (C3 -C4) alkyl, halo (C1 -C4) alkyl, halo (C1 -C4) alkoxy, (C1 -C4) alkoxy, halo (C1 -C4) alkylthio, OH, CN, NO2, or NH2, at least two of R1 to R4 being H;
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Y is X--W--Ar, X is O, or NR7, or CR8 R9 ; Z is H, Cl, OCH3, CH3, or CCl3 ; R7 is H, (C1 -C4) alkyl, or acetyl; R8 and R9 are independently H, (C1 -C4)alkyl, (C1 -C4) acyl, halo or OH, or R8 and R9 combine to form a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms; W is an alkylene chain 2 to 8 carbon atoms long, that optionally includes a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms, and optionally is substituted with (C1 -C3) alkyl, (C2 -C4) alkenyl, phenyl, (C3 -C8) cycloalkyl, halo, hydroxy, or acetyl; and Ar is imidazolyl, indolyl, thienyl, optionally substituted with CH3 or Cl, thiazolyl, - View Dependent Claims (5, 29, 48, 55, 56, 57, 58, 59, 60, 61, 62, 63)
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2. 3-benzodioxolyl,
fluorenyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl (hexahydrophenyl), cyclohexenyl (tetrahydrophenyl), naphthyl, substituted naphthyl, dihydronaphthyl, tetrahydronaphthyl, decahydronaphthyl, pyridyl, substituted pyridyl, 2,3-dihydroindenyl, or a group of the formula (2): - ##STR14## where R10 to R14 are independently H, halo, I, (C1 -C10) alkyl, branched (C3 -C6) alkyl, halo (C1 -C7) alkyl, (C1 -C7) alkoxy, halo (C1 -C7) alkoxy, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio, substituted phenylthio, NH2, NO2, OH, acetoxy, CN, SiR15 R16 R17, OSiR15 R16 R17, where R15, R16, and R17 are independently C1 -C4 alkyl, C3 -C4 branched alkyl, phenyl, or substituted phenyl, at least two of R10 to R14 being H;
or an acid addition salt of a compound of formula (1); provided that; (a) if Y is NR7 --W--Ar, then R4 is F, or Ar is naphthyl or a group of formula (2) wherein at least one of R10 to R14 is phenyl, substituted phenyl, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, halo (C1 -C4) alkyl, or halo (C1 -C4) alkoxy; and (b) the compound 4-(3-phenylpropyl)quinazoline is excluded.
- ##STR14## where R10 to R14 are independently H, halo, I, (C1 -C10) alkyl, branched (C3 -C6) alkyl, halo (C1 -C7) alkyl, (C1 -C7) alkoxy, halo (C1 -C7) alkoxy, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio, substituted phenylthio, NH2, NO2, OH, acetoxy, CN, SiR15 R16 R17, OSiR15 R16 R17, where R15, R16, and R17 are independently C1 -C4 alkyl, C3 -C4 branched alkyl, phenyl, or substituted phenyl, at least two of R10 to R14 being H;
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3. A compound of the formula (1) ##STR15## wherein R1 to R4 are independently H, halo, (C1 -C4) alkyl, branched (C3 -C4) alkyl, halo (C1 -C4) alkyl, (C1 -C4) alkoxy, NO2, or NH2,
provided that at least two of R1 to R4 are H; -
Y is X--W--Ar, X is O, or NR7 ; Z is H, Cl, OCH3, CH3, or CCl3 ; R7 is H, (C1 -C4) alkyl, or acetyl; W is an alkylene chain 2 to 6 carbon atoms long, optionally including a carbocyclic ring or substituted with (C1 -C3) alkyl, phenyl, (C3 -C8) cycloalkyl, halo, hydroxy, or acetyl; and Ar is imidazolyl, indolyl, thienyl, optionally substituted with CH3 or Cl, thiazolyl, - View Dependent Claims (6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 49, 50, 51, 52, 53, 54)
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4. 3-benzodioxolyl,
fluorenyl, cyclohexyl (hexahydrophenyl), cyclohexenyl (tetrahydrophenyl), naphthyl, dihydronaphthyl, tetrahydronaphthyl, decahydronaphthyl, or a group of the formula (2): - ##STR16## where R10 to R14 are independently H, halo, I, (C1 -C10) alkyl, branched (C3 -C6) alkyl, halo (C1 -C4) alkyl, (C1 -C4) alkoxy, halo (C1 -C4) alkoxy, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio, substituted phenylthio, NH2, NO2, OH, or CN, at least two of R10 to R14 being H;
or an acid addition salt of a compound of formula (1); provided that; if Y is NR7 --W--Ar, then Ar is naphthyl or a group of formula (2) wherein at least one of R10 to R14 is phenyl, substituted phenyl, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, halo(C1 -C4)alkyl, or halo(C1 -C4)alkoxy.
- ##STR16## where R10 to R14 are independently H, halo, I, (C1 -C10) alkyl, branched (C3 -C6) alkyl, halo (C1 -C4) alkyl, (C1 -C4) alkoxy, halo (C1 -C4) alkoxy, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio, substituted phenylthio, NH2, NO2, OH, or CN, at least two of R10 to R14 being H;
Specification
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Current AssigneeMargarita International Comercio E Services Limitada
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Original AssigneeDowElanco Co. (Corteva, Inc.)
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InventorsDreikorn, Barry A., Suhr, Robert G., Jourdan, Glen P.
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Primary Examiner(s)Richter, Johann
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Assistant Examiner(s)SCALZO, CATHERINE KILBY
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Application NumberUS08/093,975Time in Patent Office652 DaysField of Search544/284-287, 544/291-293, 514/259, 514/260US Class Current514/266.3CPC Class CodesA01N 43/54 1,3-Diazines; Hydrogenated ...C07D 239/74 with only hydrogen atoms, h...C07D 239/88 Oxygen atomsC07D 239/94 Nitrogen atomsC07D 239/95 with hetero atoms directly ...C07D 405/06 linked by a carbon chain co...C07D 409/06 linked by a carbon chain co...
