WO1994026722A1 - Fungicidal fused bicyclic pyrimidinones - Google Patents

Fungicidal fused bicyclic pyrimidinones Download PDF

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Publication number
WO1994026722A1
WO1994026722A1 PCT/US1994/004965 US9404965W WO9426722A1 WO 1994026722 A1 WO1994026722 A1 WO 1994026722A1 US 9404965 W US9404965 W US 9404965W WO 9426722 A1 WO9426722 A1 WO 9426722A1
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Prior art keywords
alkyl
optionally substituted
haloalkyl
cycloalkyl
haloalkenyl
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PCT/US1994/004965
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English (en)
French (fr)
Inventor
James Francis Bereznak
Zen-Yu Chang
Thomas Paul Selby
Charlene Gross Sternberg
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E.I. Du Pont De Nemours And Company
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Publication date
Priority to PL94311641A priority Critical patent/PL174704B1/pl
Priority to DE69428533T priority patent/DE69428533T2/de
Priority to BR9406662A priority patent/BR9406662A/pt
Priority to AT94917917T priority patent/ATE206406T1/de
Priority to JP6525540A priority patent/JPH08510243A/ja
Priority to AU69443/94A priority patent/AU6944394A/en
Priority to DK94917917T priority patent/DK0698013T3/da
Priority to SK1402-95A priority patent/SK140295A3/sk
Application filed by E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to US08/545,827 priority patent/US5747497A/en
Priority to RU95121800A priority patent/RU2139862C1/ru
Priority to EP94917917A priority patent/EP0698013B1/en
Publication of WO1994026722A1 publication Critical patent/WO1994026722A1/en
Priority to LVP-95-339A priority patent/LV11464B/en
Priority to GR20010401811T priority patent/GR3036942T3/el
Priority to FR09C0038C priority patent/FR09C0038I2/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C07D239/96—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • This invention relates to certain 4(3H)-quinazolinones, their agriculturally suitable salts and compositions, and methods of their use as general or selective fungicides, in particular for the control of cereal powdery mildew both preventive and curative.
  • This invention comprises compounds of Formulae I, II, and in including all geometric and stereoisomers, N-oxides, agriculturally-suitable salts thereof, agricultural compositions containing them and their use as fungicides:
  • n 0, 1 or 2;
  • Q is independently O or S
  • R 1 is C 3 -C 10 alkyl; C 3 -C 5 cycloalkyl; C 4 -C 10 alkenyl; C 4 -C 10 alkynyl; C 1 -C 10 haloalkyl; C 3 -C 10 haloalkenyl; C 3 -C 10 haloalkynyl; C 2 -C 10 alkoxyalkyl; C 2 -C 10 alkylthioalkyl; C 2 -C 10 alkylsulfinylalkyl; C 2 -C 10 alkylsulfonylalkyl; C 5 -C 10 cycloalkylalkyl; C 4 -C 10 alkenyloxyalkyl; C 4 -C 10 alkynyloxyalkyl; C 4 -C 10 (cycloalkyl)oxyalkyl; C 4 -C 10 alkenylthioalkyl; C 4 -C 10 alkynylthioalkyl
  • alkynylthioalkyl C 6 -C 10 (cycloalkyl)thioalkyl; C 2 -C 10 haloalkoxyalkyl; C 4 -C 10 haloalkenyloxyalkyl; C 4 -C 10 haloalkynyloxyalkyl; C 4 -C 10 alkoxyalkenyl; C 4 -C 10 alkoxyalkynyl; C 4 -C 10 alkylthioalkenyl; C 4 -C 10 all ⁇ lthioalkynyl; C 4 -C 10 trialkylsilylalkyl; C 3 -C 10 cyanoalkyl; C 2 -C 10 nitroalkyl; C 1 -C 10 alkyl substituted with CO 2 R 11 , NR 11 R 12 , or phenyl optionally substituted with R 13 , R 15 , and R 16 ; phenyl optionally substituted withR 13 , R 15 , and R 16
  • R 1 and R 2 are taken together to form -CH 2 (CH 2 ) m CH 2 -;
  • n 1-4;
  • R 3 is halogen; C 1 -C 8 alkyl; C 3 -C 8 cycloalkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C 1 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 haloalkynyl; C 1 -C 8 alkoxy; C 1 -C 8 haloalkoxy; C 3 -C 8 alkenyloxy; C 3 -C 8 alkynyloxy; C 1 -C 8 alkylthio; C 3 -C 8 alkenylthio; C 3 -C 8 alkynylthio; C 1 -C 8 alkylsulfinyl; C 1 -C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulf
  • R 4 is hydrogen; halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 1 -C 4 alkoxy; or C 1 -C 4 haloalkoxy;
  • R 5 is C 3 -C 5 alkyl; C 7 -C 10 alkyl; C 4 -C 7 alkenyl; C3-C5 alkynyl; C 1 -C 10 haloalkyl;
  • haloalkoxyalkyl C 4 -C 10 haloalkenyloxyalkyl; C 4 -C 10 haloalkynyloxyalkyl; C 4 -C 10 alkoxyalkenyl; C 4 -C 10 alkoxyalkynyl; C 4 -C 10 alkylthioalkenyl;
  • haloalkoxyalkyl C 4 -C 10 haloalkenyloxyalkyl; C 4 -C 10 haloalkynyloxyalkyl; C 4 -C 10 alkoxyalkenyl; C 4 -C 10 alkoxyalkynyl; C 4 -C 10 alkylthioalkenyl;
  • R 5 and R 6 are taken together to form -CH 2 (CH 2 ) m CH 2 -;
  • R 7 is C 3 -C 10 alkyl; C 3 -C 7 cycloalkyl; C 4 -C 7 alkenyl; propynyl; C 5 -C 10 alkynyl;
  • haloalkenyloxyalkyl C 4 -C 10 haloalkynyloxyalkyl; C 4 -C 10 alkoxyalkenyl; C 4 -C 10 alkoxyalkynyl; C 4 -C 10 alkylthioalkenyl; C 4 -C 10 alkylthioalkynyl; C 4 -C 10 trialkylsilylalkyl; C 1 -C 10 alkyl substituted with NR 1 1 R 12 or nitro; C 2 -C 10 alkyl substituted with cyano; C 1 -C 10 alkoxy; C 1 -C 10 haloalkoxy; C 1 -C 10 alkylthio; C 1 -C 10 haloalkylthio; NR 12 R 17 ; or phenyl, pyridyl, furanyl thienyl, naphthyl, benzofiiranyl, benzothienyl, or quinolinyl each
  • R 9 is hydrogen; C 2 -C 10 alkyl; C 3 -C 7 cycloalkyl; C 3 -C 10 alkenyl; C 3 -C 10 alkynyl;
  • (cycloalkyl)thioalkyl; C 2 -C 10 haloalkoxyalkyl; C 4 -C 10 haloalkenyloxyalkyl; C 4 -C 10 haloalkynyloxyalkyl; C 4 -C 10 alkoxyalkenyl; C 4 -C 10 alkoxyalkynyl; C 4 -C 10 alkylthioalkenyl; C 4 -C 10 alkylthioalkynyl; C 4 -C 10 trialkylsilylalkyl; C 1 -C 10 alkyl substituted with NR 11 R 12 ; C 4 - C10 cyanoalkyl; C 2 -C 10 nitroalkyl; C 1 -C 8 alkyl substituted with CO 2 R 11 ; pyridyl, furanyl, thienyl, or naphthyl each optionally substituted with R 14 , R 15 , and R 16 ; -N CR 11 R
  • R 7 and R 9 are taken together to form -CH 2 (CH 2 ) m CH 2 -;
  • R 10 is hydrogen; C 1 -C 4 alkyl; C 1 -C 4 alkoxy; or NR 11 R 12 ;
  • R 11 is independently hydrogen; C 1 -C 4 alkyl; or phenyl optionally substituted with at least one R 13 ;
  • R 12 is independently hydrogen; C 1 -C 8 alkyl; or phenyl optionally substituted with at least one R 13 ; or
  • R 11 and R 12 are taken together to form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 (CH 2 ) 3 CH 2 -,
  • R 13 is independently halogen; C 1 -C 4 alkyl; C 1 -C 4 alkoxy; C 1 -C 4 haloalkyl; nitro; or cyano;
  • R 14 is independently C 1 -C 6 alkyl; C 1 -C 8 alkoxy; C 1 -C 8 haloalkyl; halogen; C 2 -C 8 alkynyl; C 1 -C 6 thioalkyl; phenyl or phenoxy each optionally substituted with at least one R 13 ; cyano; nitro; C 1 -C 8 haloalkoxy; C 1 -C 8 haloalkylthio; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; acetyl; CO 2 Me; or N(C 1 -C 2 alkyl) 2 ; R 15 is independently methyl; ethyl; methoxy; methylthio; halogen; or
  • R 16 is independently halogen
  • R 17 is independently C 1 -C 8 alkyl; or phenyl optionally substituted with at least one R 13 .
  • alkyl used either alone or in compound words such as “alkylthio,” “haloalkyl,” or “alkylthioalkyl” denotes straight-chain or branched alkyl; e.g., methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl, hexyl, etc. isomers.
  • Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • cycloalkyloxyalkyl denotes the cycloalkyl groups linked through an oxygen atom to an alkyl chain. Examples include cyclopentyloxymethyl and cyclohexyloxybutyl.
  • cycloalkylthioalkyl are the cycloalkyl groups linked through a sulfur atom to an alkyl chain; e.g., cyclopropylthiopentyl.
  • Cycloalkylalkyl denotes a cycloalkyl ring attached to a branched or straight-chain alkyl; e.g. cyclopropylmethyl and
  • Alkenyl denotes straight chain or branched alkenes; e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl , pentenyl, hexenyl, etc. isomers. Alkenyl also denotes polyenes such as 1,3-hexadiene and 2,4,6-heptatriene.
  • Alkenyl also denotes polyenes such as 1,3-hexadiene and 2,4,6-heptatriene.
  • Alkenyl also denotes polyenes such as 1,3-hexadiene and 2,4,6-heptatriene.
  • Alkenyl denotes straight chain or branched alkynes; e.g., ethynyl, 1 -propynyl, 3-propynyl and the different butynyl, pentynyl, hexynyl, etc. isomers.
  • Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy, hexyloxy, etc. isomers.
  • alkylthioalkenyl and alkylthioalkynyl examples include
  • alkenyloxyalkyl denotes groups in which the alkenyloxy moiety is attached to an alkyl group. Examples include
  • H 2 C CHCH 2 OCH 2 CH 2
  • H 2 C CHCH 2 OCH(CH 3 )CH 2
  • alkenylthioalkyl denotes the alkenylthio moieties bonded to an alkyl group. Examples include
  • Alkynyloxy denotes straight or branched alkynyloxy moieties. Examples include HC ⁇ CCH 2 O, CH 3 C ⁇ CCH 2 O and CH 3 C ⁇ CCH 2 CH 2 O. "Alkynyloxyalkyl” denotes alkynyloxy moieties bonded to alkyl groups; e.g., CH 3 CSCCH 2 OCH 2 CH 2 and
  • Alkynylthioalkyl denotes alkynylthio moieties bonded to alkyl groups.
  • Example include CH 3 C ⁇ CCH 2 SCH 2 CH 2 and
  • Alkylthio denotes methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylthioalkyl denotes alkylthio groups attached to an alkyl chain; e.g., CH 3 CH 2 SCH 2 CH(CH 3 ) and (CH 3 ) 2 CHSCH 2 .
  • Alkylsulfinyl denotes both enantiomers of an alkylsulfinyl group. For example, CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsufinyl isomers.
  • Alkylsulfinylalkyl denotes alkylsulfinyl groups attached to an alkyl chain; e.g., CH 3 CH 2 S(O)CH 2 CH(CH 3 ) and (CH 3 ) 2 CHS(O)CH 2 .
  • alkylsulfonyl examples include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 ,
  • Alkylsulfonylalkyl denotes alkylsulfonyl groups attached to an alkyl chain; e.g., CH 3 CH 2 S(O) 2 CH 2 CH(CH 3 ) and (CH 3 ) 2 CHS(O) 2 CH 2 .
  • Haloalkenyloxyalkyl denotes haloalkenyl groups bonded to oxygen and in turn bonded to alkyl groups. Examples include
  • haloalkynyl include HC ⁇ CCHCl, CF 3 C ⁇ C, CCl 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
  • Haloalkynyloxyalkyl denotes haloalkynyl groups bonded through an oxygen atom to an alkyl moiety.
  • Examples include CF 3 C ⁇ CCH 2 OCH 2 CH 2 , ClCH 2 C ⁇ CCH 2 CH 2 OCH(CH 3 ), etc.
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, CF 2 HCH 2 CH 2 O and CF 3 CH 2 O.
  • Haloalkoxyalkyl denotes haloalkoxy groups bonded to straight-chain or branched alkyl groups; e.g., CF 2 HCH 2 CH 2 OCH 2 CH 2 , CCl 3 CH 2 OCH(CH 3 ) and CF 3 OCH 2 .
  • Trialkylsilyl designates a group with three alkyl groups bonded to silicon; e.g., (CH 3 ) 3 Si and t-Bu(CH 3 ) 2 Si.
  • “Trialkylsilylalkyl” denotes trialkylsilyl groups bonded to another straight-chain or branched alkyl group. Examples include (CH 3 ) 3 SiCH 2 and t-Bu(CH 3 ) 2 SiCH 2 CH(CH 3 )CH 2 .
  • C i -C j The total number of carbon atoms in a substituent group is indicated by the "C i -C j " prefix where i and j are numbers from 1 to 10.
  • C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkoxy designates
  • CH 3 OCH 2 O; C 3 alkoxyalkoxy designates, for example, CH 3 OCH 2 CH 2 O or
  • CH 3 CH 2 OCH 2 O; and C 4 alkoxyalkoxy designates the various isomers of an alkoxy group substituted with a second alkoxy group containing a total of 4 carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 O, and CH 3 CH 2 OCH 2 CH 2 O.
  • alkoxyalkyl examples include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 ,
  • R 1 is C 3 -C 8 alkyl; C 4 -C 8 alkenyl; C 4 -C 8 alkynyl; C 1 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 5 -C 8 cycloalkylalkyl; C 2 -C 8 alkyl substituted with cyano; C 1 -C 8 alkoxy; C 1 -C 8 haloalkoxy; C 1 -C 8 alkylthio; or C 4 -C 8 alkenyloxyalkyl; or pyridyl, furanyl, or thienyl each optionally substituted with R 14 and R 15 ; R 2 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 1 -C 8 haloalkyl;
  • R 3 is halogen; C 1 -C 8 alkyl; C 2 -C 8 alkynyl; C 3 -C 8 cycloalkyl; C 1 -C 8
  • haloalkyl C 1 -C 8 alkoxy; C 1 -C 8 haloalkoxy; C 1 -C 8 alkylthio; C 1 -C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; or C 5 -C 8 trialkylsilylalkynyl; and
  • R 14 is methyl; ethyl; methoxy; ethoxy; C 1 -C 2 haloalkyl; halogen; acetylenyl; propargyl; methylthio; ethylthio; cyano; nitro; C 1 -C 2 haloalkoxy; vinyl; allyl; acetyl; CO 2 Me; or N(C 1 -C 2 alkyl) 2 .
  • n O
  • R 3 is halogen; C 1 -C 8 alkyl; C 2 -C 8 alkynyl; C 3 -C 8 cycloalkyl; C 1 -C 8
  • haloalkyl C 1 -C 8 alkoxy; C 1 -C 8 haloalkoxy; C 1 -C 8 alkylthio; C 1 -C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; or C 5 -C 8 trialkylsilylalkynyl;
  • R 5 is C 3 -C 5 alkyl; C 4 -C 7 alkenyl; C 3 -C 5 alkynyl; C 1 -C 8 haloalkyl; C 5 -C 8 haloalkenyl; C 2 -C 8 alkoxyalkyl other than methoxypropyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C 2 -C 8 alkyl substituted with cyano; C 1 -C 8 alkoxy; C 1 -C 8 haloalkoxy; C 1 -C 8 alkylthio; or C 4 -C 8 alkenyloxyalkyl; or phenyl, furanyl, or thienyl each optionally substituted with R 14 and R 15 ;
  • R 6 is C 3 -C 8 alkyl; C 3 -C 7 alkenyl; C 3 -C 8 alkynyl; C 1 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl other than propoxymethyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C 5 -C 8 cyanoalkyl; C 4 -C 8 alkenyloxyalkyl; phenyl optionally substituted with R 13 ; or C 3 -C 5 alkyl substituted with phenyl optionally substituted with R 13 and R 15 ; and
  • R 14 is methyl; ethyl; methoxy; ethoxy; C 1 -C 2 haloalkyl; halogen; acetylenyl; propargyl; methylthio; ethylthio; cyano; nitro; C 1 -C 2 haloalkoxy; vinyl; allyl; acetyl; CO 2 Me; or N(C 1 -C 2 alkyl) 2 .
  • R 3 is halogen; C 1 -C 8 alkyl; C 2 -C 8 alkynyl; C 3 -C 8 cycloalkyl; C 1 -C 8
  • haloalkyl C 1 -C 8 alkoxy; C 1 -C 8 haloalkoxy; C 1 -C 8 alkylthio; C 1 -C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; or C 5 -C 8 trialkylsilylalkynyl;
  • R 7 is C 3 -C 8 alkyl; C 4 -C 7 alkenyl; propynyl; C 2 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkyl substituted with cyano; C 1 -C 8 alkoxy; C 1 -C 8 haloalkoxy; C 1 -C 8 alkylthio; or C 4 -C 8 alkenyloxyalkyl; or phenyl, pyridyl, furanyl, or thienyl each optionally substituted with R 14 and R 15 ; R 9 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3
  • R 3 and R 4 are both iodine and R 9 is phenyl optionally substituted with R 14 and R 15 ;
  • R 14 is methyl; ethyl; methoxy; ethoxy; C 1 -C 2 haloalkyl; halogen; acetylenyl; propargyl; methylthio; ethylthio; cyano; nitro; C 1 -C 2 haloalkoxy; vinyl; allyl; acetyl; CO 2 Me; or N(C 1 -C 2 alkyl) 2 .
  • R 1 is C 3 -C 8 alkyl; C 4 -C 8 alkenyl; C 4 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; or thienyl optionally substituted with at least one of R 14 and R 15 ;
  • R 2 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; or phenyl optionally substituted with R 13 ;
  • R 3 is halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 1 -C 4 alkoxy; C 1 -C 4
  • haloalkoxy acetylenyl; or trimethylsilylacetylenyl;
  • R 5 is C 3 -C 5 alkyl; C 4 -C 7 alkenyl; C 3 -C 5 alkynyl; C 3 -C 8 haloalkyl; C 5 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; or phenyl or thienyl each optionally substituted with R 14 and R 15 ;
  • R 6 is C 3 -C 8 alkyl; C 3 -C 7 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; or phenyl optionally substituted with R 13 ;
  • R 7 is C 3 -C 8 alkyl; C 4 -C 7 alkenyl; propynyl; C 3 -C 8 haloalkyl; C 3 -C 8
  • haloalkenyl C 3 -C 8 alkoxy; C 3 -C 8 alkoxyalkyl; or phenyl or thienyl each optionally substituted with R 14 and R 15 ;
  • R 9 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; -NR 12 R 17 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substituted with R 14 and R 15 ; and R 14 is methyl; ethyl; methoxy; methylthio; halogen; trifluoromethyl; or N(C 1 -C 2 alkyl) 2 .
  • Preferred 5 The compounds of Preferred 4 wherein:
  • R 1 is C 3 -C 8 alkyl; C 4 -C 8 alkenyl; C 4 -C 8 alkynyl; C 3 -C 8 haloalkyl; or
  • R 2 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; or phenyl optionally substituted with R 13 ;
  • R 3 is halogen
  • R 4 is hydrogen or halogen
  • R 5 is C 3 -C 5 alkyl; C 4 -C 7 alkenyl; C 3 -C 5 alkynyl; C 3 -C 8 haloalkyl; or C 5 -C 8 haloalkenyl; or phenyl optionally substituted with R 14 and R 15 ;
  • R 6 is C 3 -C 8 alkyl; C 3 -C 7 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; or phenyl optionally substituted with R 13 ;
  • R 7 is C 3 -C 8 alkyl; C 4 -C 7 alkenyl; propynyl; C 3 -C 8 haloalkyl; or C 3 -C 8 haloalkenyl; or phenyl optionally substituted with R 14 and R 15 ; and R 9 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; -NR 12 R 17 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substituted with R 14 and R 15 .
  • compounds of Formulae Ia and Ib, IIa-IIc, and IIla-IIIe are various subsets of the compounds of Formulae I, II, and III. All substituents in compounds of Formulae la and lb, IIa-IIc, and IIIa-IIIe and 2-7 are as defined above for Formulae I, II, and IIl.
  • Stereoisomers of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers and geometric isomers.
  • One skilled in the art will appreciate that one stereoisomer may be more active than the others and how to separate said stereoisomers.
  • the present invention comprises mixtures, individual stereoisomers, and optically active mixtures of compounds of Formulae I, II, and III as well as agriculturally suitable salts thereof.
  • An anthranilic acid (2-aminobenzoic acid) of Formula 2 is condensed with an isothiocyanate of Formula R 1 -NCS to form the 2-thioquinazolinedione of Formula 3.
  • This condensation is preferably performed in the presence of a base such as triethylamine.
  • Formula 4 is treated with a mixture of a base, for example sodium hydride, in R 2 OH solvent.
  • a base for example sodium hydride
  • the reaction mixture is stirred at a temperature from about 0°C to 120°C for
  • the desired 2-R 2 O-4(3H)-quinazolinone can be isolated from the reaction mixture by extraction into a water-immiscible solvent, and purified by chromatography or recrystallization. Similar synthetic procedures are described in U.S. 3,755,582, incorporated herein by reference.
  • Anthranilic acids of Formula 2 are known or can be prepared by known methods. For example see, March, J. Advanced Organic Chemistry; 3rd ed., John Wiley:
  • the isothiocyanates of Formula R*-NCS can be prepared from the corresponding amine by treatment with thiophosgene as known in the art. For example, see J. Heterocycl. Chem., (1990), 27, 407.
  • 2-thioquinazolinediones of Formula 3 can be prepared by treatment of the (C 1 -C 4 alkyl) anthranilic acid ester of Formula 5 with thiophosgene to form the isothiocyanate ester, followed by treatment with an amine of formula R 1 NH 2
  • the anthranilic acid ester of Formula 5 is treated with thiophosgene at a temperature from about -20°C to 100°C for 1 to 48 hours optionally in an inert solvent. Often this reaction is performed in a biphasic mixture in the presence of a base, such as calcium carbonate, and an acid, such as aqueous hydrochloric acid.
  • a base such as calcium carbonate
  • an acid such as aqueous hydrochloric acid.
  • the resulting isothiocyanate may be isolated by extraction into a water-immiscible solvent, such as methylene chloride, followed by drying of the organic extracts and evaporation under reduced pressure.
  • the isothiocyanate can be combined in situ with the amine of Formula H 2 NR 1 and stirred at about -20°C to 50°C for 0.1 to 24 hours.
  • the desired 2-thioquinazolinediones of Formula 3 can be isolated from the reaction mixture by aqueous extraction, and purified by chromatography or recrystallization. Similar synthetic procedures are described in J. Heterocycl. Chem., (1990), 27, 407.
  • the 2-thioquinazolinedione is dissolved or dispersed in an inert solvent such as dimethylformamide and treated with a base at a temperature from about -20°C to 60°C with a base.
  • the reaction mixture may then be heated to just above ambient temperature to the reflux temperature of the solvent for 0.1 to 24 hours to effect deprotonation. After cooling, the reaction mixture is cooled and treated with R 6 -X and stirred for 0.1-24 hours at a temperature from about 20°C to the reflux temperature of the solvent.
  • the quinazolinone of Formula Ha can be isolated by extraction into a water-immiscible solvent, and purified by chromatography or recrystallization.
  • One method of preparation of compounds of Formula IIIa is by treatment of a
  • 2-methylthio-4(3H)-quinazolinone of Formula 7 (Z SMe) with an excess of an amine of Formula HNR 8 R 9 at about 150°C to 175°C.
  • compounds of Formula Ia and IIa can be prepared by displacement of the 2-chlorine in the appropriate 4(3H)-quinazolinone, rather than by displacement of the 2-SCH 3 group (Scheme 1) or S-alkylation of the thiocarbonyl (Scheme 4).
  • quinazolinethiones of Formula IIlb can be prepared by treatment of the corresponding quinazolinone with P 2 S 5 or Lawesson's reagent (Scheme 8).
  • Salts of compounds of Formulae I, II, and III can be formed by treating the free base of the corresponding compound with strong acids such as hydrochloric or sulfuric acid. Salts can also be prepared by alkylation of a tertiary amine group in the molecule to form, for example, the trialkylammonium salt. N-Oxides of compounds of Formulae I, II, and III can be made by oxidizing the corresponding reduced nitrogen compound with a strong oxidizing agent such as meta-chloroperoxybenzoic acid.
  • Step D To 150 mL of propanol cooled to approximately -60°C was added 0.83 g of ⁇ aH (60% active in oil) with stirring. To this mixture at -60°C was added 6.5 g of the purified product obtained in Step B. The mixture was allowed to warm to room temperature and stirred for approximately 48 h to yield a clear solution. The reaction solution was poured into water and extracted twice with diethyl ether. The ether extracts were washed twice with water, dried over magnesium sulfate, filtered and the filtrate was then evaporated to yield 10.3 g of an oil. Thin layer chromatography indicated starting material and desired product were both present. Step D
  • Step B To a solution containing 1.02 g of the purified product obtained in Step B dissolved in 25 mL of tetrahydrofuran was added 0.5 mL of n-propylamine. The reaction mixture was stirred for approximately 24 h at room temperature. The reaction was then filtered and the filtrate was evaporated to obtain an oil. The oil was dissolved in diethyl ether and washed twice with water and once with brine. The ether solution was dried over magnesium sulfate, filtered and the filtrate was then evaporated to yield 0.74 g of the title compound as a white solid, m.p.
  • Ph phenyl
  • the fimgicidal compositions of the present invention comprise an effective amount of at least one compound of Formula I, II, or in as defined above and at least one of (a) a surfactant, (b) an organic solvent, and (c) at least one solid or liquid diluent.
  • Useful formulations can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent.
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill. Water-dispersible granules can be produced by agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., (1988), pp 251-259.
  • Suspensions are prepared by wet-milling; see, for example, U.S. 3,060,084.
  • Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical
  • Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in DE 3,246,493.
  • the compounds of this invention are useful as plant disease control agents, especially for the control of cereal powdery mildews (e.g., Erysiphe graminisf. sp. tritici, the causal agent of wheat powdery mildew).
  • the present invention therefore further comprises a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, or to the plant seed or seedling to be protected, an effective amount of a compound of Formula I, II, or III or a fungicidal composition containing said compound.
  • the compounds and compositions of this invention provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and
  • Deuteromycete classes are effective in controlling a broad spectrum of plant diseases, particularly fohar pathogens of ornamental, vegetable, field, cereal, and fruit crops. These pathogens include Plasmopara viticola, Phytophthora infestans,
  • Peronospora tabacina Pseudoperonospora cubensis, Pythium aphanidermatum, Alterriaria brassicae, Septoria nodorum, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaera leucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Puccinia arachidis, Rhizoctonia solani, Sphaerotheca fuliginea, Fusarium oxysporum, Verticillium dahliae, Pythium aphanidermat
  • insecticides fungicides, nematocides, bactericides, acaricides, semiochemicals, repellants, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • insecticides such as acephate, avermectin B, azinphosmethyl, bifenthrin, biphenate, buprofezin, carbofuran, chlordimeform, chlorpyrifos, cyfluthrin, deltamethrin, diazinon, diflubenzuron, dimethoate, esfenvalerate, fenpropathrin, fenvalerate, fipronil, flucythrinate, flufenprox, fluvalinate, fonophos, isofenphos, malathion, metaldehyde, metha-midophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, oxamyl, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon,
  • insecticides such as acephate, averme
  • combinations with other fungicides having a similiar spectrum of control but a different mode of action will be particularly advantageous for resistance management.
  • Preferred combinations comprise a compound of Formula I, II, or III, and a fungicide selected from the group flusilazole, cyproconazole, tetraconazole,
  • Plant disease control is ordinarily accomplished by applying an effective amount of a compound of this invention either pre- or post-infection, to the portion of the plant to be protected such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media (soil or sand) in which the plants to be protected are growing.
  • the compounds can also be applied to the seed to protect the seed and seedling.
  • Rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions. Foliage can normally be protected when treated at a rate of from less than 1 g/ha to 5,000 g/ha of active ingredient. Seed and seedlings can normally be protected when seed is treated at a rate of from 0.1 to 10 g per kilogram of seed.
  • TESTS demonstrate the control efficacy of compounds of this invention on specific pathogens.
  • the pathogen control protection afforded by the compounds is not limited, however, to these species. See Index Tables A, B, and C for compound descriptions.
  • Test compounds were first dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem ® 014 (polyhydric alcohol esters). The resulting test suspensions were then used in the following tests.
  • Trem ® 014 polyhydric alcohol esters
  • test suspension was sprayed to the point of run-off on wheat seedlings. The following day the seedlings were inoculated with a spore dust of Erysiphe graminis f. sp. tritici, (the causal agent of wheat powdery mildew) and incubated in a growth chamber at 20°C for 7 days, after which disease ratings were made.
  • test suspension was sprayed to the point of run-off on wheat seedlings.
  • seedlings were inoculated with a spore suspension of Puccinia recondita (the causal agent of wheat leaf rust) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 6 days, after which disease ratings were made.
  • Puccinia recondita the causal agent of wheat leaf rust
  • test suspension was sprayed to the point of run-off on tomato seedlings.
  • seedlings were inoculated with a spore suspension of Phytophthora infestans (the causal agent of potato and tomato late blight) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 5 days, after which disease ratings were made.
  • Phytophthora infestans the causal agent of potato and tomato late blight
  • test suspension was sprayed to the point of run-off on grape seedlings.
  • seedlings were inoculated with a spore suspension of Plasmopara viticola (the causal agent of grape downy mildew) and incubated in a saturated atmosphere at 20°C for 24 h, moved to a growth chamber at 20°C for 6 days,and then incubated in a saturated atmosphere at 20°C for 24 h, after which disease ratings were made.
  • Plasmopara viticola the causal agent of grape downy mildew
  • test suspension was sprayed to the point of run-off on cucumber seedlings.
  • seedlings were inoculated with a spore suspension of Botrytis cinerea (the causal agent of gray mold on many crops) and incubated in a saturated atmosphere at 20°C for 48 h, and moved to a growth chamber at 20°C for 5 days, after which disease ratings were made.
  • Botrytis cinerea the causal agent of gray mold on many crops

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DK94917917T DK0698013T3 (da) 1993-05-12 1994-05-10 Fungicide kondenserede bicykliske pyrimidinoner
BR9406662A BR9406662A (pt) 1993-05-12 1994-05-10 Composto metodo de controle de doenças de plantas composição fungicida e método de controle de mildio de pó de trigo
AT94917917T ATE206406T1 (de) 1993-05-12 1994-05-10 Fungizide kondensierte bizyklische pyrimidinone
JP6525540A JPH08510243A (ja) 1993-05-12 1994-05-10 殺菌・殺カビ性の縮合二環式ピリミジノン類
AU69443/94A AU6944394A (en) 1993-05-12 1994-05-10 Fungicidal fused bicyclic pyrimidinones
SK1402-95A SK140295A3 (en) 1993-05-12 1994-05-10 Condensed bicyclic pyrimidinones, fungicidal agents on their base and inhibition method of plant deseases by using them
US08/545,827 US5747497A (en) 1993-05-12 1994-05-10 Fungicidal fused bicyclic pyrimidinones
PL94311641A PL174704B1 (pl) 1993-05-12 1994-05-10 Nowe 4(3H)-chinazolinony i środek grzybobójczy do zwalczania mączniaka pszenicy
DE69428533T DE69428533T2 (de) 1993-05-12 1994-05-10 Fungizide kondensierte bizyklische pyrimidinone
RU95121800A RU2139862C1 (ru) 1993-05-12 1994-05-10 Замещенные 4(3н)-хиназолиноны, обладающие фунгицидными свойствами, композиции на их основе и способы борьбы с мучнистой росой
EP94917917A EP0698013B1 (en) 1993-05-12 1994-05-10 Fungicidal fused bicyclic pyrimidinones
LVP-95-339A LV11464B (en) 1993-05-12 1995-11-10 Fungicidal fused bicyclic pyrimidinones
GR20010401811T GR3036942T3 (en) 1993-05-12 2001-10-18 Fungicidal fused bicyclic pyrimidinones
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