SUBSTITUTED PYRIDO[1,2-A]PYRIMIDINONE DERIVATIVES AS FUNGICIDES

Abstract: Substituted pyrido[1,2-a]pyrimidinone compounds of formula (I) wherein Q is O or S; W is O; S; S(O); S(O)2; NH; or NR<9>; X is CR<3> or N; Y is CR<4> or N; Z is CR<5>=CR<6>; CR<5>=N; N=CR<6>; S; O; or NR<7>; and R<1>, R<2>, R<3>, R<4>, R<5>, R<6> and R<7> are various groups; and agricultural compositions containing one or more such compounds useful as fungicides for control of diseases in plants are disclosed.

Description: TITLE SUBSTITUTED PYRIDO ( 1 ,2-A) PYRIMIDINONE DERIVATIVES AS FUNGICIDES This invention relates to certain substituted pyrido[1,2*-a]pyrimidinone compounds useful as fungicides, their agriculturally suitable salts and compositions, and methods of their use as general or selective fungicides, in particular for the control of wheat powdery mildew both preventive and curative- Urban et al., Helv. Chi . Acta, 1970, 53, 905, disclose pyrido[1,2-a]pyrimidinones of Formula i and their use as analgesics and antiinflammatory agents. U.S. 3,755,582 issued August 28, 1973 and U.S. 3,867,384 issued February 18, 1975, each disclose 4 (3H)-quinazolinones of Formula ii and their use as agricultural fungicides. 11 wherein: is 0; S or NH; and Z is 0 or S. SUMMARY OF THE INVENTION This invention comprises compounds of Formula ϊ including all geometric and stereoisomers, N-oxides, agriculturally-suitable salts thereof, agricultural compositions containing them and method of use of said compounds, salts, or compositions as fungicides, wherein: Q is 0 or S; is O; S; S(O) ; S(0) 2 ; NH; or NR 9 ; X is CR 3 or N; Y is CR 4 or N; Z is CR 5 =CR 6 ; CR 5 =N; N=CR 6 ; S; O; or NR 7 ; having the directionality of the CR 5 =CR 6 r CR 5 =N and N=CR 6 linkages such that the moiety depicted on the left side of the double bond is bonded to Y and the moiety on the right side of the double bond is bonded to the ring junction; R 1 is C- j^ -C- Lβ alkyl; C 3 -C 7 cycloalkyl; C 2 -C 18 alkenyl; C 2 -C 18 alkynyl; C-L-C--^ haloalkyl; C 2 -C 1 8 haloalkenyl; C 2 -C 18 haloalkynyl; C 2 -C 18 alkoxyalkyl; C 2 -C 18 alk lthioalkyl; C 2 -C 18 alkylsulfinylalkyl; C 2 -C 18 alkylsulfonylalkyl; C 4 -C 18 cycloalkylalkyl; C 4 -C 18 alkenyloxyalkyl; C 4 -C 18 alkynyloxyalkyl; C 4 -C 18 cycloalkyloxy- alkyl; C 4 -C 18 alkenylthioalkyl; C 4 -C 18 alkynyl- thioalkyl; C 6 -C 18 cycloalkylthioalkyl; C 2 -C 18 haloalkoxyalkyl; C 3 -C 18 haloalkenyloxyalkyl; C -C 18 haloalkynyloxyalkyl; C 4 -C 18 alkoxy- alkenyl; C 4 -C 18 alkoxyalkynyl; C 4 -C 18 alkylthio- alkenyl; C 4 -C 18 alkylthioalkynyl; C -C 18 trialkylsilylalkyl; C 1 -C 1 Q alkyl substituted with NR 8 R 10 , cyano, or nitro; C 1 -C 8 alkyl substituted with C0 2 R 8 ; C-L-C-LS alkoxy; C^C ; **^ haloalkoxy; C 3 -C 18 alkynyloxy; C 3 -C 18 alkenyl- oxy; C-*_-C 18 alkylthio; C 3 -C 18 alkenylthio; or C 3 -C 18 alkynylthio; R 2 is Ci-C*-^ alkyl; C 3 -C 7 cycloalkyl; C 3 -C 18 alkenyl; C 3 -C 18 alkynyl; C 1 -C 18 haloalkyl; C 3 ~C 18 haloalkenyl; C 3 -C 18 haloalkynyl; C 2 -C 18 alkoxyalkyl; C 2 -C 18 alkylthioalkyl; C 2 -C 18 alkylsulfinylalkyl; C 2 -C 18 alkylsulfonylalkyl; C -C 18 cycloalkylalkyl; C 4 -C 18 alkenyloxyalkyl; C 4 -C 18 alkynyloxyalkyl; C 4 -C 18 cycloalkyloxy- alkyl; C 4 -C 18 alkenylthioalkyl; C -C 18 alkynyl- thioalkyl; C 6 -C 18 cycloalkylthioalkyl; C 2 -C 18 haloalkoxyalkyl; C 3 -C 18 haloalkenyloxyalkyl; C -C 18 haloalkynyloxyalkyl; C 4 -C 18 alkoxy- alkenyl; C 4 -C 18 alkoxyalkynyl; C 4 -C 18 alkylthio- alkenyl; C -C 18 alkylthioalkynyl; C 4 -C 18 trialkylsilylalkyl; C 1 -C 18 alkyl substituted with NR 8 R 10 ; C 2 -C 18 cyanoalkyl; C 2 -C 18 nitroalkyl; C 1 -C 8 alkyl substituted with C0 2 R 8 ; or phenyl, benzyl, or phenethyl each optionally substituted on the phenyl ring with R 13 ; or R 1 and R 2 can be taken together along with the C=C-W fragment to which they are attached to form a 5-7 membered ring in which the R 1 -R 2 bridge is a saturated, all-carbon chain optionally substituted with C-L-C**^ alkyl; R 3 and R 5 are each independently hydrogen; halogen; C ! -C 4 alkyl; C 1 -C 4 haloalkyl; C 1 -C alkoxy; or C 2 -C haloalkoxy; R 4 and R 6 are each independently hydrogen; halogen; c ι -c 8 alkyl; C 3 -C 8 cycloalkyl; C 2 -C 8 alkenyl; C -C 8 alkynyl; Ci-Cs haloalkyl; C 3 -C 8 halo- alkenyl; C 3 -C 8 haloalkynyl; C-L-C**-* alkoxy; C- L -Cg 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-^-O Q alkylsulfinyl; C-^-C β alkyl- sulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthio- alkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkyl¬ sulfonylalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; cyano; nitro; carbomethoxy; carboethoxy; or NR^R 12 ; R 7 is C 1 -C 4 alkyl or C-*_-C 4 haloalkyl; R 8 and R 9 are each independently O -C^ alkyl; R 10 and R 11 are each independently H or C x -C 4 alkyl; R 12 is C- L -Cg alkyl; R 8' and R 10 , or the groups R 11 and R 12 , can be taken together to form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 (CH 2 ) 3 CH 2 -, -CH 2 CH 2 0CH 2 CH 2 -, -CH 2 CH(Me) CH 2 CH(Me)CH 2 - r or -CH 2 CH(Me)OCH(Me) CH 2 -; and R 13 is halogen; C x -C 4 alkyl, C 1 -C alkoxy, or C 1 -C haloalkyl; provided that: i) when Z is CR 5 =CR 6 , then at least one substituent selected from the group consisting of R 3 , R 4 , R 5 and R 6 , is hydrogen; and ii) the total number of carbons in R 3 , R 4 , R 5 and R 6 is equal to or less than 16; iii) the total number of nitrogen atoms incorporated into the bicyclic framework is less than or equal to four; iv) R 3 and R 4 are not both hydrogen; and v) X and Y are not both nitrogen. Preferred for reasons of ease of synthesis or greater fungicidal activity are compounds of Formula I, denoted as Preferred 1, wherein: ' is 0; S; NH; or NR 9 ; X is CR 3 ; Y is CR 4 ; R 1 is C-i-Cs alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C 1 -C 8 haloalkyl; C 2 -C 8 haloalkenyl; C 2 -C 8 alkoxyalkyl; C -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C 2 -C 8 cyanoalkyl; Ci-Ce alkoxy; C*-_-C 18 haloalkoxy; C 3 -C 8 alkenyloxy; C 3 -C 8 alkenylthio; or C 4 -C 8 alkenyloxyalkyl; R 2 is C- j^ -C β alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C 1 -C 8 haloalkyl; C -C 8 haloalkenyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C -C 8 cycloalkylalkyl; C 2 -C 8 cyanoalkyl; C 4 -C 8 alkenyloxyalkyl; or phenyl optionally substituted with R 13 ; and R 4 and R 6 are each independently hydrogen; halogen; C-^Cs alkyl; C 3 -C 8 cycloalkyl; - j^ -Cs haloalkyl; C^C**** alkoxy; C- j^ -Cs haloalkoxy; C- j^ -Ce alkylthio; C 1 -C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; or cyano. More preferred are compounds denoted as Preferred f the above Preferred 1, wherein: Q is 0; is 0; S; NH; or NMe; Z is CR 5 =CR 6 ; CR 5 =N; S; or 0; R 1 is C- j^ -Ce alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C*]_-C 8 haloalkyl; C 2 -C 8 halo¬ alkenyl; Ci-Cs alkoxy; C 2 -C 8 alkoxyalkyl; or C 3 -C 8 alkenyloxy; R 2 is C-±-C Q alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C*-_-C 8 haloalkyl; C -C 8 halo- alkenyl; C 2 -C 8 alkoxyalkyl; or phenyl optionally substituted with R 13 ; and R 4 and R 6 are each independently hydrogen; halogen; C-L-C-J alkyl; C 1 -C 8 haloalkyl; c l _c 8 alkoxy; C x -C 8 haloalkoxy; C 3 -C 8 trialkylsilyl; or cyano. Even more preferred are compounds denoted as Preferred 3, of the above Preferred 2, wherein: Z is CR 5 =CR 6 or S; R 1 is C -C Q alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C- j^ -Cs haloalkyl; or C 2 -C 8 haloalkenyl; R 2 is C±-C Q alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C**_-C 8 haloalkyl; C 2 -C 8 haloalkenyl; or phenyl optionally substituted with R 13 ; and R 4 and R 6 are each independently hydrogen; halogen; C-L-C-3 alkyl; C 1 -C 8 haloalkyl; CJ ^ -C Q alkoxy; or C* j _-C 8 haloalkoxy. Specifically preferred are compounds of Preferred 3 wherein said compounds are: 7-bromo-3- (n-propyl)-2-(n-propyloxy)-4H- pyrido[1 Λ 2-a]pyrimidin-4-one; 7,9-dibromo-3-(n-propyl) -2-(n-propyloxy)-4H- pyrido[1,2-a]pyrimidin-4-one; or 7-iodo-3- (-α-propyl)-2-(n-propyloxy)-4H- pyrido[l,2-a]pyrimidin-4-one. DETAILED DESCRIPTION OF THE INVENTION In the above recitations, the term "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. The term "cycloalkyl- oxyalkyl" denotes the cycloalkyl groups linked through an oxygen atom to an alkyl chain. Examples include cyclopentyloxymethyl and cyclohexyloxybutyl. The terπi "cycloalkylthioalkyl" are the cycloalkyl groups linked through a sulfur atom to an alkyl chain; e.g., cyclo- propylthiopentyl . "Cycloalkylalkyl" denotes a cycloalkyl ring attached to a branched or straight- chain alkyl; e.g. cyclopropylmethyl and cyclohexyl- butyl . "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. "Alkynyl" denotes straight chain or branched alkynes; e.g., ethynyl, 1-propynyl, 3-propynyl and the different butynyl, pentynyl, hexynyl, etc. isomers. "Alkynyl" can also denote moieties comprised of multiple triple bonds; e.g., 2, 7-octadiyne and 2, 5, 8-decatriyne. "Alkoxy" denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy, hexyloxy, etc. isomers. "Alkoxyalkenyl" and "alkoxy- alkynyl" denoted groups in which the alkoxy group is bonded throught the oxygen atom to an alkenyl or alkynyl group, respectively. Examples include CH 3 OCH 2 CH=CH and (CH 3 ) 2 CH0CH 2 C=CCH 2 . The corresponding sulfur derivatives are denoted "alkylthioalkenyl and "alkylthioalkynyl." Examples of the former include CH 3 SCH 2 CH=CH and CH 3 CH 2 SCH2 (CH 3 ) CH=CHCH 2 , and an example of the latter is CH 3 CH 2 CH 2 CH 2 SCH 2 C=C. "Alkenyloxy" denotes straight chain or branched alkenyloxy moieties. Examples of alkenyloxy include H 2 C=CHCH 2 0, (CH 3 ) 2 C=CHCH 2 0, (CH 3 ) CH=CHCH 2 0, (CH 3 )CH=C(CH 3 )CH 2 0 and CH 2 =CHCH 2 CH 2 0. "Alkenylthio" denotes the similar groups wherein the oxygen atom is replace with a sulfur atom; e.g., H 2 C=CHCH 2 S and (CH 3 )CH=C(CH 3 )CH 2 S. The term "alkenyloxyalkyl" denotes groups in which the alkenyloxy moiety is attached to an alkyl group. Examples include H 2 C=CHCH 2 0CH 2 CH 2 , H 2 C=CHCH 2 OCH(CH 3 )CH 2Λ etc. "Alkenylthioalkyl" denotes the alkenylthio moieties bonded to an alkyl group. Examples include H 2 C=CHCH 2 SCH(CH 3 ) CH(CH 3 ) and (CH 3 ) CH=C(CH 3 ) CH 2 SCH 2 . "Alkynyloxy" denotes straight or branched alkynyloxy moieties. Examples include HC≡CCH 2 0, CH 3 C=CCH 2 0 and CH 3 C-=CCH 2 CH 2 0. "Alkynyloxyalkyl" denotes alkynyloxy moieties bonded to alk l groups; e.g., CH 3 C≡CCH 2 OCH 2 CH 2 and HC=CCH 2 OCH(CH 3 ) CH 2 . "Alkynylthioalkyl" denotes alkynylthio moieties bonded to alkyl groups. Example include CH 3 C≡CCH 2 SCH CH 2 and CH 3 C=CCH 2 CH 2 SCH(CH 3 )CH 2 . "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 (0) , CH 3 CH 2 S (0) , CH 3 CH 2 CH 2 S (0) , (CH 3 ) 2 CHS(0) and the different but lsulfinyl, pentylsulfinyl and hexylsufinyl isomers. "Alkylsulfinylalkyl" denotes alkylsulfinyl groups attached to an alkyl chain; e.g., CH 3 CH 2 S(0)CH 2 CH(CH 3 ) and (CH 3 ) 2 CHS(0)CH 2 . Examples of "alkylsulfonyl" include CH 3 S(0) 2 , CH 3 CH 2 S(0) 2 , CH 3 CH 2 CH 2 S(0) 2r (CH 3 ) 2 CHS (O) 2 and the different butylsulfonyl, pentylsulfonyl and hexyl- sulfonyl isomers. "Alkylsulfonylalkyl" denotes alkyl- sulfonyl groups attached to an alkyl chain; e.g., CH 3 CH 2 S(0) 2 CH 2 CH(CH 3 ) and (CH 3 ) 2 CHS (0) 2 CH 2 . 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 F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CF 2 . Examples of "haloalkenyl" include (Cl) 2 C=CHCH 2 and CF 3 CH 2 CH=CHCH 2 . "Haloalkenyloxyalkyl" denotes haloalkenyl groups bonded to oxygen and in turn bonded to alkyl groups. Examples include CF 3 CH 2 CH=CHCH 2 0CH2 and (Cl) 2 C=CHCH 2 0CH 2 CH 2 . Examples of "haloalkynyl" include HC≡CCHCl, CF 3 C---C, CC1 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 , C1CH 2 C=CCH 2 CH 2 0CH(CH 3 ) , etc. Examples of "haloalkoxy" include CF 3 0, CC1 3 CH 2 0, CF 2 HCH 2 CH 2 0 and CF 3 CH 2 0. "Haloalkoxyalkyl" denotes haloalkoxy groups bonded to straight-chain or branched alkyl groups; e.g., CF 2 HCH 2 CH 2 0CH 2 CH 2 , CC1 3 CH 2 0CH(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 . The total number of carbon atoms in a substituent group is indicated by the "Ci-Cj" prefix where i and j are numbers from 1 to 20. For example, C 1 -C 3 alkyl- sulfonyl designates methylsulfonyl through propyl- sulfonyl; C 2 alkoxyalkoxy designates CH 3 OCH 2 0; C 3 alkoxyalkoxy designates, for example, CH 3 OCH CH 2 0 or CH 3 CH 2 OCH 0; 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 0, and CH 3 CH 2 OCH 2 CH 2 0. Examples of "alkoxyalkyl" include CH 3 0CH 2 , CH 3 0CH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 . Compounds of Formula I can be prepared using one or more of the reactions and techniques described in Schemes 1-4 hereinafter, or by following the procedures given in Examples 1-6. The variables , X, Y, and Z and substituents R 1 -R 13 in the compounds of Formulae Ia-Ig and II-VII illustrated in Schemes 1-4 hereinafter are defined as for compounds of Formula I above. The general method for preparing compounds of Formula la is shown in Scheme 1. Based on a known synthetic method (A. E. Tschitschibabin, Chem. Ber. , 1924, 57, 168; G. R. Lappin, et. al., J. Org. Chem., 1950, 15, 377; A. R. Katritzky and A. J. Waring, J. Chem. Soc , 1962, 1544; J. Klosa, J. Prakt . Chem. , 1964, 26, 150; K. E. Schulte and J. Witt, Arch . Pharm., 1958, 252, 298) , heating substituted aminoheterocycles of Formula II with substituted malonates of Formula III neat at 150-250°C or by heating in a high boiling solvent such as diethylbenzene (and allowing for the evaporation or distillation of ethanol formed in the reaction) gives zwitterionic intermediates of Formula IV. Substituted aminoheterocycles of Formula II and malonates of Formula III are known and in many cases are commercially available. Reaction of heterocycles of Formula IV with alkylating agents in the presence of base can give rise to alkylation on both oxygen and nitrogen (R. Urban, Helv. Chim. Acta, 1970, 53, 905) . However, alkylation of heterocycles of Formula IV with reagents of Formula R 2 L wherein L is Cl, Br, I, OTs or OMs, in the presence of a mild base, such as potassium carbonate, in a polar aprotic solvent, such as dimeth lformamide, affords predominantly the desired O-alkylated product of Formula la with only a small amount of the more polar (by thin layer chromatograph ) N-alkylated mesoionic adduct of Formula V being obtained. Products of Formulae la and V can be separated by chromatography. Scheme 1 II IV As illustrated in Scheme 2, heating intermediates of Formula IV in thionyl chloride or phosphorous oxychloride furnishes chloro-substituted heterocycles of Formula VI. Displacement of the chloro substituent, by reacting heterocycles of Formula VI with nucleo- philic reagents of Formula R 2 GH (generally in the presence of base, e.g., sodium hydride or sodium methoxide, in a solvent such as tetrahydrofuran or dimethylformamide) gives products of Formula lb wherein G is 0, S, NH, or NR 9 . Oxidation of compounds of Formula lb wherein G is S with a suitable oxidizing agent such as meta-chloroperoxybenzoic acid furnishes products of Formula Ic. Scheme 2 lb Ic n=l or 2 G=0, S,NH, NR 3 Thiation of heterocycles of Formula Id with phosphorous pentasulfide or Lawesson ' s reagent gives thiones of Formula Ie (Scheme 3) . Scheme 3 Id Ie Compounds of Formula If can be made by the procedure illustrated in Scheme 4. Intermediates of Formula Ig can be initially prepared by the methods shown in Schemes 1 and 2 whereby diethylmalonate is used as the malonate starting material (i.e., compounds of Formula III wherein R 1 = H) in Scheme 1. Bromination of compounds of Formula Ig with bromine or N-bromosuccinimide (NBS) yields brominated adducts of Formula VII which can be coupled with stannanes of Formula R 14 Sn(CH 3 ) 3 in the presence of a palladium catalyst such as tetrakis (triphenylphosphine)- palladium(O) or bis (triphenylphosphine)palladium(II) chloride to afford products of Formula If. Bromoheterocycles of Formula VII can also be coupled with terminal alkynes using palladium catalysis in the presence of base (such as triethylamine) and cuprous iodide. Scheme 4 If .14 alkenyl or alkynyl Salts of compounds of Formula I can be formed by treating the free base of Formula I with strong acids such as hydrochloric or sulfuric acid. N-oxides of compounds of Formula I can be made by oxidizing compounds of Formula I with a strong oxidizing agent such as jneta-chloroperoxybenzoic acid. INTERMEDIATE 1 Preparation of 7-Chloro-2-hydroxy-4-oxo-3- (2-propenyl) - pyridoPI, 2-alpyrimidin-l-ium Hydroxide,, Inner Salt A mixture of 10.0 g (77.8 mmol) of 2-amino-5- chloropyridine and 23.0 g (115 mmol) of diethyl allyl- malonate in 60 mL of diethylbenzene was heated at reflux for 1 h with stirring. Ethanol generated during heating was removed by distillation. A solution initially formed followed by gradual precipitation of a yellow solid. On cooling, n-butyl chloride was added to enhance precipitation of this solid which was filtered, washed with -o-butyl chloride, and dried. A 13.5 g yield of the title compound (m.p. 284-287°C) was obtained and used in subsequent steps without further purification. EXAMPLE 1 Preparation of 7-Chloro-2-methoxy-3- (2-propenyl)-4H- pyridofl.2-a-pyrimidin-4-onβ To 2.0 g (8.5 mmol) of 7-chloro-2-hydroxy-4-oxo-3- (2-propenyl)-pyrido[1,2-a]pyrimidin-1-ium hydroxide, inner salt and 3.5 g (25.4 mmol) of potassium carbonate stirring in 50 mL of N Λ N-dimethylformamide, 2.6 mL of iodomethane was added and the mixture was stirred at room temperature for 18 h. Excess water and 200 L of ethyl acetate were added. The organic layer was separated, washed with water (3 times) and brine, and dried over magnesium sulfate. The solvent was evaporated in vacυo to give a dark oil which was flash chromatographed on silica gel (1:1 hexane/ethyl acetate) to afford 0.7 g of the title compound, m.p. 139-141°C; ^-H NMR (CDC1 3 ) : δ 9.05 (d, 1H) , 7.65, 7.60 (dd, 1H), 7,45 (d, 1H) , 6.05-5.85 (m, 1H) , 5.15-4.95 (m, 2H) , 4.03 (s, 3H) , 3.40 (d, 2H) . EXAMPLE 2 Preparation of 7-Chloro-3- (2-propenyl) -2-(2- propenyloxy) -4H-pyrido ϊl .2-a]pyrimidin-4-one To 1.0 g (4.2 mmol) of 7-chloro-2-hydroxy-4-oxo-3- (2-propenyl) -pyrido[1,2-a]pyrimidin-1-ium hydroxide, inner salt and 1.5 g (10.8 mmol) of potassium carbonate stirring in 35 mL of N Λ N-dimethy1formamide, 0.9 mL of allyl bromide was added and the mixture stirred at room temperature for 15 h. Excess water was added and the aqueous mixture was extracted with 125 mL of ethyl acetate. The organic layer was then washed with water (3 times) and brine and dried over magnesium sulfate. Evaporating in vacuo gave a solid residue which was flash chromatographed on silica gel (3:1 followed by 1:1 hexane/ethyl acetate) to afford 0.55 g of the title compound, m.p. 104-105°C; 1 H NMR (CDC1 3 ) : δ 9.07 (d, 1H) , 7.63 (broad d, 1H) , 7.42 (d, 1H) , 6.10-5.90 (m, 2H) , 5.42 (broad d, 1H) , 5.25, 5.23 (dd, 1H) , 5.13 (d, 1H) , 5.05-4.95 (m, 3H) , 3.42 (d, 2H) . INTERMEDIATE 2 Preparation of 7-Chloro-2-hydroxy-4-oxo-3-propyl- pyrido[1,2-alpyrimidin-1-ium Hydroxide, Inner Salt A mixture of 11.5 g (89.4 mmol) of 2-amino-5- chloropyridine and 49.0 g (242 mmol) of diethyl propyl- malonate was heated neat at 175°C for 3.5 h. Ethanol formed during heating was allowed to evaporate. A solution formed initially followed by gradual precipitation of a yellow solid. After cooling, 25 mL of hexane were added and the solid was filtered, washed with hexane, and dried to yield 8.0 g of the title compound. This solid (m.p. 298-305°C) was used without further purification in the subsequent steps . EXAMPLE 3 Preparation of 7-Chloro-2-methoxy-3-propyl- 4H-pyridofl,2-a]pyrimidin-4-one To 5.0 g (21.0 mmol) of 7-chloro-2-hydroxy-4-oxo-3- propyl-pyrido[l, 2-a]pyrimidin-l-ium hydroxide, inner salt and 4.3 g (31.2 mmol) of potassium carbonate stirring in 35 ml of N,N-dimethylformamide, 4.5 g (31.7 mmol) of iodomethane was added and the mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between 250 mL of water and 250 mL of ethyl acetate and the organic layer was separated followed by washing with water (3 times) and brine. After drying over magnesium sulfate, the solvent was removed in vacuo to give a yellow solid residue which was flash chromatographed on silica gel (5:1 followed by 3:1 hexane/ethyl acetate) to afford 2.8 g of the title compound, m.p. 135-137°C; ^-H NMR (CDC1 3 ) : δ 9.07 (d, IH), 7.65, 7.60 (dd, IH) , 7.45 (d, IH), 4.02 (s, 3H) , 2.63 (t, 2H) , 1.70-1.50 (m, 2H) , 0.97 (t, 3H) . EXAMPLE 4 Preparation of 7-Chloro-3-propyl-2-propyloxy- 4H-pyridof r -a]pyrimidin-4-one To 7.0 g (29 mmol) of 7-chloro-2-hydroxy-4-oxo-3- propyl-pyrido[l,2-a]pyrimidin-l-ium hydroxide, inner salt and 5.7 g (41 mmol) of potassium carbonate stirring in 35 mL of N, N-dimethylformamide, 6.5 g (38 mmol) of n-propyl iodide was added and the mixture stirred at room temperature for 14 h. The reaction mixture was partitioned between 150 mL of water and 200 mL of ethyl acetate and the organic layer separated followed by washing with water (3 times) and brine. After drying over magnesium sulfate, the solvent was evaporated in vacuo to give a yellow solid residue which was flash chromatographed on silica gel (10:1-5:1-3:1 hexane/ethyl acetate) to afford 5.2 g of the title compound as a white solid, m.p. 105-107°C; X E NMR (CDC1 3 ) : δ 9.04 (d, IH) , 7.60 (dd, IH) , 7.42 (d, IH), 4.37 (t, 2H), 2.63 (t, 2H) , 1.80 (q, 2H) , 1.60 (q, 2H) , 1.10-0.90 (m, 6H) . INTERMEDIATE 3 Preparation of 2 f 7-Dichloro-3-propyl-4H- pyridofl ,2-alpyrimidin-4-one A mixture of 10.0 g (42 mmol) of 7-chloro-2- hydroxy-4-oxo-3-propyl-pyrido[1,2-a]pyrimidin-1-ium hydroxide, inner salt stirring in 80 mL of phosphorous oxychloride was heated at reflux for 88 h. The dark reaction mixture was poured onto a large excess of ice. After extracting the resulting aqueous mixture with 800 mL of ethyl acetate, the organic layer was washed with water (2 times) , saturated sodium bicarbonate and brine and dried over magnesium sulfate. Evaporating in vacuo gave dark oily/solid residue which was flashed chromatographed on silica gel (10:1-5:1-3:1 hexane/ethyl acetate) to give 1.8 g of the title compound, m.p. 169-171°C; 2 H NMR (CDC1 3 ) : δ 8.99 (d, IH), 7.67 (dd, IH) , 7.55 (d, IH) , 2.80 (t, 2H) , 1.65 (q, 2H) , 1.02 (t, 3H) . EXAMPLE 5 Preparation of 7-Chloro-3-propyl-2-propylthio- 4H-pyridoTl,2-a!pyrimidin-4-one To 0.5 g (2.0 mmol) of 2, 7-dichloro-3-propyl-4H- pyrido[1,2-a]pyrimidin-4-one and 0.43 g (3.1 mmol) of potassium carbonate stirring in 30 mL of N,JV-dimethyl- formamide at room temperature, 0.21 mL (2.3 mmol) of 1-propanethiol was added and the reaction was stirred at room temperature for 5 h. Water (75 mL) and ethyl acetate (125 L) were added and the organic layer was separated and washed with water (3 times) and brine followed by drying over magnesium sulfate. Evaporation of solvent in vacuo provided an oily solid residue which was flash chromatographed on silica gel (15:1-10:1 hexane/ethyl acetate) to yield 0.27 g of the title compound, m.p. 91-93°C; R NMR (CDC1 3 ) : δ 9.0 (d, IH) , 7.55 (dd, IH) , 7.44 (d, IH) , 3.22 (t, 2H) , 2.68 (t, 2H) , 1.75 (q, 2H) , 1.65 (q, 2H) , 0.99-1.07 (m, 6H) . EXAMPLE 6 Preparation of 7-Chloro-3-propyl-2-propyloxy- 4H-pyridori-.2-a1pyrimidin-4-th.ione A mixture of 1.0 g (3.6 mmol) of 7-chloro-3-propyl- 2-propyloxy-4H-pyrido[l,2-a]pyrimidin-4-one and 4.7 g (11 mmol) of phosphorous pentasulfide was heated at reflux for 32 h. An additional 3.0 g (6.8 mmol) of phosphorous pentasulfide was added and the mixture was heated at reflux for an additional 16 h. After partitioning the reaction mixture between 150 mL of ethyl acetate and 10% aqueous hydrogen chloride, the organic layer was separated and washed with 10% aqueous hydrogen chloride (3 times with 100 mL) , saturated sodium bicarbonate, and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo to give a solid residue. Flash column chromatography on silica gel (n-butyl chloride) afforded 0.16 g of the title compound, m.p. 117-120°C; E NMR (CDC1 3 ) : δ 10.63 (d, 1H) Γ 7.75 (dd, IH) , 7.57 (d, IH) , 4.43 (t, 2H) , 3.07 (t, 2H) , 1.84 (q, 2H) , 1.68 (q, 2H) , 0.95-1.15 (m, 6H) . Using the procedures outlined in Schemes 1-4, the compounds of Tables 1-7 can be prepared. Ih Ii I Ik II The following abbreviations are used in the tables which follow. t - is tertiary OMe - is ethoxy s - is secondary SEt - is ethylthio n - is normal CN - is cyano i - is iso TMS - is trimethylsilyl Me - is methyl S(0)Me - is methylsulfinyl Et - is ethyl S(0) Me - is methylsulfonyl Ph - is phenyl TABLE 1 Compounds of Formula Ih R 3 =R 5 =H; W=Q ___ .si Me Me Et n-propyl -i-propyl Me 2-propenyl Me 2-propenyl 2-propenyl 2-propenyl Λ-propyl n-propyl 2-propenyl 2-propenyl Λ-propyl 2-propenyl 2-propenyl 2-propenyl π-butyl Et n-propyl Et Et Et 2-propenyl R 1 Me n-propyl Me 2-propenyl -•--hexyl Me n-butyl Et i-propyl n-propyl Me n-propyl n-propyl i-propyl 2-propenyl 2-propenyl n-propyl Me 2-propenyl n-propyl Me ιι-heptyl Et -π-dodecyl Me Et n-propyl 2-propenyl 2-propenyl 2-propenyl 2-propenyl n-propyl 2-butenyl 2-propenyl -5-butyl Me ά-pentyl 2-propenyl n-dodecyl n-hexyl 2-propenyl 2-propenyl n-propyl 2-propenyl 2-propenyl 2-propenyl n-propyl Et 2-butenyl 2-propenyl n-propyl (CH 2 ) 17 Me 2-propenyl 2-propenyl 2-pentenyl n-propyl 2-hexenyl 2-butenyl 2-propenyl 2-propenyl n-propyl Me n-oσtyl n-heptyl Me (CH 2> ll Me n-propyl s-butyl -- i R p Me F Me CH 2 CH 2 SEt F F Me cyclohexylmethyl Br Et Et cyclooctyl I H Me phenethyl Cl H Et CH 2 CH 2 CN Cl H Me CH 2 CH 2 N0 2 Cl H 2-propenyl cyclopropylmethyl Cl Cl Et benzyl Br Me n-propyl phenyl Cl H Et 4-chlorophenyl Cl H n-propoxy n-butyl CF** H ethoxy 2-propenyl Br H methoxy (CH 2 ) 17 Me Cl H n-propyl CH 2 CH=CHC1 Cl H 0CH 2 CH 2 C1 2-butenyl 3 H CH 2 C(C1)=CH 2 n-butyl Br Me CH 2 CH=CHC1 CH 2 CH=CMe 2 t-butyl H CH 2 CH=CMe 2 OCH 2 CF 3 CH=CHMe H Me cyclohexyl C≡CMe H Me n-butyl OCH 2 C≡CH H Et 2-c clohexenyl S(0)Me H Et CH 2 C≡CCF 3 CH 2 S(O)Me H Me Et CN H .n-propyl 2-propenyl C0 2 Me H Et .n-propyl C0 2 Et H Et 2-butenyl Cl cyclohexyl Et Et Cl CH=CHMe Et Et Cl C-≡CEt Me n-pentyl Cl CH 2 Br Me 2-butynyl Me CF 3 2-propenyl 2-propenyl Cl CH=CHCF 3 n-butyl Me Cl C---CCF 3 n-propyl n-propyl Br 0CH 2 C≡CH n-propyl CH 2 CH 2 C1 . i .si _s± Cl H Et 4-methylbenzyl Cl H Et 4-CF -benzyl Cl H Et 3-CF 3 -phenethyl Cl H Et 4-methoxybenzyl Cl H Me 4-methoxyphenethyl .si CH=CHCF 3 CH 2 CH=CHC1 n-propyl Et n-butyl Me 2-dodecenyl CH 2 CH 2 OEt Me n-propyl 2-propenyl 2-propenyl 2-propenyl n-propyl Et 2-propenyl 2-butenyl n-propyl n-propyl n-butyl n-hexyl i-propyl Et i-butyl Me s-pentyl 2-propenyl Me 2-hexenyl Et 2-butynyl n-butyl CH 2 CH 2 OMe 2-propenyl CH 2 SCHMe 2 2-pentenyl 1-butenyl phenyl Me 4-chlorophenyl R 3 =R 5 =H o4 ϋ. -Si JSi Cl H S (0) n-propyl n-propyl Br H S (0) 2 n-pentyl Et ∞3 Me S (0) 2 i-propyl n-propyl --si --si --Si --Q. J- --Si ___ H Cl Me O NH n-propyl phenyl H OCH 2 CHMe 2 H O NMe n-butyl Me H Br H 0 NH 2-propenyl phenyl H Br H O NH CH 2 CH 2 OMe 4-chlorophenyl H Cl H S NEt n-hexyl n-butyl H Cl H O NH Et benzyl Me Me H O O i-pentyl Et H I H O 0 CH 2 OCH 2 CH=CH 2 n-propyl H Cl H S O CH 2 SCH 2 CH 2 Me Et H CF 3 H O S 2-butenyl Me H CF 3 H O S Me phenyl H Cl H O O CH 2 C(C1)=CH 2 n-propyl H Me Cl 0 0 n-propyl 2-pentenyl TABLE 7 compounds of Formula I _Q .Si s o o 2-propenyl n-propyl s o 0 2-propenyl 2-propenyl s o o n-butyl n-hexyl s o 0 s-butyl 2-butenyl s o o Et 2-pentenyl s o o n-propyl 2-propenyl s o o 2-propenyl n-propyl s o o 2-butenyl Et s o o Me n-propyl s o o CH 2 CH 2 0Me Et s o 0 CH 2 CH 2 C1 2-hexenyl s o o 2-propenyl 2-propenyl s o o 2-butenyl n-propyl s o 0 CH=CHMe n-heptyl s o s n-butyl Et s s o 2-propenyl 2-butenyl s o o 2-butynyl 2-pentenyl Compounds of this invention will generally be used in an agriculturally suitable composition. The compositions of this invention comprise an effective amount of a compound of Formula I 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 include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. 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. Weight Percent Wettable Powders Oil Suspensions, Emulsions, Solutions, (including Emulsifiable Concentrates) Dusts Granules, Baits and Pellets High Strength Compositions Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc. 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 be 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 Engineering, December 4, 1967, pp 147-148, Perry 's Chemical Engineer 's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pp 8-57 and following, and WO 91/13546. 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. For further information regarding the art of formulation, see U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al.. Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989. In the following Examples, all percentages are by weight and all formulations are worked up in conventional ways. Compound numbers refer to compounds in Index Tables A and B, hereinafter. Example A Wettable Powder Compound 3 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%. Example B Granule Compound 3 10.0% attapulgite granules (low volative matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%. Example C Extruded Pellet Compound 3 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%. Example D Emulsifiable Concentrate Compound 3 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%. The compounds and compositions of this invention are usef l as plant disease control agents. 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, to the media in which the plant to be protected is growing, or to the plant seed or seedling an effective amount of a compound of Formula I, an N-oxide thereof, an agriculturally suitable salt thereof, or a fungicidal composition containing said compound, N-oxide, or salt. 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. They are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal, and fruit crops. These pathogens include Plasmopara viticola, Phytophthora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, Alternaria 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 aphanidermatum, Phytophthora megasperma and other generea and species closely related to these pathogens. They are particularly effective in the control of Erysiphe graminis, the causal agent of wheat powdery mildew, both preventive and curative. Compounds of this invention can also be mixed with one or more other 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. Examples of other agricultural protectants with which compounds of this invention can be formulated are: insecticides such as monocrotophos, carbofuran, tetrachlorvinphos, malathion, parathioπ-methyl, methomyl, chlordimeform, diazinon, deltamethrin, oxamyl, fenvalerate, esfenvalerate, permethrin, profenofos, sulprofos, triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb, acephate, azinphosmethyl, chlorpyrifos, dimethoate, fipronil, flufenprox, fonophos, isofenphos, methidathion, methamidophos, phosmet, phosphamidon, phosalone, pirimicarb, phorate, terbufos, trichlorfon, methoxychlor, bifenthrin, biphenate, cyfluthrin, fenpropathrin, fluvalinate, flucythrinate, tralomethrin, metaldehyde and rotenone; fungicides such as carbendazim, thiuram Λ dodine, maneb, chloroneb, benomyl, cymoxanil, fenpropidine, fenpropimorph, . triadimefon, captan, thiophanate-methyl, thiabendazole, phosethyl-Al, chlorothalonil, dichloran, metalaxyl, captafol, iprodione, oxadixyl, vinclozolin, kasugamycin, myclobutanil, tebuconazole, difeno- conazole, diniconazole,- fluquinconazole, ipconazole, me conazole, penconazole, propiconazole, uniconzole, flutriafol, prochloraz, pyrifenox, fenarimol, triadimenol, diclobutrazol, copper oxychloride, furalaxyl, folpet, flusilazol, blasticidin S, diclomezine, edifenphos, isoprothiolane, iprobenfos, mepronil, neo-asozin, pencycuron, probenazole, pyroquilon, tricyclazole, validamycin, and flutolanil; nematocides such as aldoxycarb, fenamiphos and fosthietan; bactericides such as oxytetracyline, streptomycin and tribasic copper sulfate; acaricides such as binapacryl, oxythioquinox, chlorobenzilate, dicofol, dienochlor, cyhexatin, hexythiazox, amitraz, propargite, tebufenpyrad and fenbutatin oxide; and biological agents such as Bacillus thuringiensis and baculovirus. In certain instances, combinations with other fungicides having a similiar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Plant disease control is ordinarily accomplished by applying an effective amount of a compound of this invention either pre- or post-infection, to the plant or 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. The'following Tests demonstrate the control efficacy of compounds of this invention on specific pathogens. The pathogen control protection a forded by the compounds is not limited, however, to these species. See Index Tables A and B 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. TEST A The 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 B The test suspension was sprayed to the point of run-off on wheat seedlings. The following day the 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. TEST C The test suspension was sprayed to the point of run-off on rice seedlings. The following day the seedlings were inoculated with a spore suspension of Pyricularia oryzae (the causal agent of rice blast) and incubated in a saturated atmosphere at 27°C for 24 h, and then moved to a growth chamber at 30°C for 5 days, after which disease ratings were made. TEST D The test suspension was sprayed to the point of run-off on tomato seedlings. The following day the 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. TEST E The test suspension was sprayed to the point of run-off on grape seedlings. The following day the 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. TEST F The test suspension was sprayed to the point of run-off on cucumber seedlings. The following day the 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. Results for Tests A-F are given in Table C. In the table, a rating of 100 indicates 100% disease control and a rating of 0 indicates no disease control (relative to the controls) . NT = Not Tested. TABLE C *The compound was spray at a concentration of 40 ppm.

Claims: What is claimed is 1. A compound of Formula I wherein: Q is 0 or S; W is O; S; S (0) ; S(0) 2 ; NH; or NR 9 ; X is CR 3 or N; Y is CR 4 or N; Z is CR 5 =CR 6 ; CR 5 =N; N=CR 6 ; S; O; or NR 7 ; having the directionality of the CR 5 =CR 6 , CR 5 =N and N=CR 6 linkages such that the moiety depicted on the left side of the double bond is bonded to Y and the moiety on the right side of the double bond is bonded to the ring junction; R 1 is L-C-LS alkyl; C 3 -C 7 cycloalkyl; C 2 -C 18 alkenyl; C 2 -C 18 alkynyl; C-L-C**^ haloalkyl; C 2 -C 18 haloalkenyl; C -C 18 haloalkynyl; C 2 -C 18 alkoxyalkyl; C 2 -C 18 alkylthioalkyl; ^ 2 ~^- \% alkylsulfinylalkyl; C -C 18 alkylsulfonylalkyl; C 4 -C 18 cycloalkylalkyl; C -C 18 alkenyloxyalkyl; c 4 ~ c i 8 alkynyloxyalkyl; C -C 18 cycloalkyloxy- alkyl; C 4 -C 18 alkenylthioalkyl; C 4 -C 18 alkynyl¬ thioalkyl; C 6 -C 18 cycloalkylthioalkyl; C 2 -C 18 haloalkoxyalkyl; C 3 -C 18 haloalkenyloxyalkyl; C 4 -C 18 haloalkynyloxyalkyl; C -C 18 alkoxy- alkenyl; C 4 -C 18 alkoxyalkynyl; C 4 -C 18 alkylthio- alkenyl; C 4 -C 18 alkylthioalkynyl; C 4 -C 18 trialkylsilylalkyl; C_-Z_ alkyl substituted with NR 8 R 10 , cyano, or nitro; C- j _-C 8 alkyl substituted with C0 2 R 8 ; C 1 -C 18 alkoxy; C 1 -C 18 haloalkoxy; C 3 -C 18 alkynyloxy; C 3 -C 18 alkenyl¬ oxy; C-L-C 18 alkylthio; C 3 -C 18 alkenylthio; or c 3 -c i 8 alkynylthio; R 2 is C 1 -C 18 alkyl; C 3 -C 7 cycloalkyl; C 3 -C 18 alkenyl; C 3 -C 18 alkynyl; C-*_-C 18 haloalkyl; C 3 -C 18 haloalkenyl; C 3 -C 18 haloalkynyl; C 2 -C 18 alkoxyalkyl; C 2 -C 18 alkylthioalkyl; C 2 -C 18 alkylsulfinylalkyl; C 2 -C 18 alkylsulfonylalkyl; C 4 -C 18 cycloalkylalkyl; C 4 -C 18 alkenyloxyalkyl; C -C 18 alkynyloxyalkyl; C 4 -C 18 cycloalkyloxy- alkyl; C 4 -C 18 alkenylthioalkyl; C -C 18 alkynyl¬ thioalkyl; C 6 -C 18 cycloalkylthioalkyl; C 2 -C 18 haloalkoxyalkyl; C 3 -C 18 haloalkenyloxyalkyl; C 4 -C l8 haloalkynyloxyalkyl; C 4 -C 18 alkoxy- alkenyl; C 4 -C 18 alkoxyalkynyl; C -C 18 alkyl- thioalkenyl; C -C 18 alkylthioalkynyl; C -C 18 trialkylsilylalkyl; C- ] _-C 18 alkyl substituted with NR 8 R 10 ; C 2 -C 18 cyanoalkyl; C 2 -C 18 nitroalkyl; C^C-^ alkyl substituted with C0 2 R 8 ; or phenyl, benzyl, or phenethyl each optionally substituted on the phenyl ring with R 13 ; or R 1 and R 2 can be taken together along with the C=C-W fragment to which they are attached to form a 5-7 membered ring in which the R-^R 2 bridge is a saturated, all-carbon chain optionally substituted with C; ] _-C 12 alkyl; R 3 and R 5 are each independently hydrogen; halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 1 -C 4 alkoxy; or C 1 -C haloalkoxy; R 4 and R 6 are each independently hydrogen; halogen; C*-_-C 8 alkyl; C 3 -C 8 cycloalkyl; C 2 -C 8 alkenyl; C -C 8 alkynyl; C**_-C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 haloalkynyl; C-L-^ alkoxy; C* ] _-C 8 haloalkoxy; C 3 -C 8 alkenyloxy; C 3 -C 8 alkynyloxy; C -C & alkylthio; C 3 -C 8 alkenylthio; C 3 ~C 8 alkynylthio; C--_-C 8 alkylsulfinyl; C -C Q alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkylsulfonylalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; cyano; nitro; C0 Me; C0 2 Et; or NR 1:L R 12 ; R 7 is C x -C 4 alkyl or C- | _-C haloalkyl; R 8 and R 9 are each independently C* j _-C 4 alkyl; R 10 and R 11 are each independently H or C 1 -C 4 alkyl; R 12 is C- j^ -Cs alkyl; R 8 and R 10 , or the groups R 11 and R 12 , can be taken together to form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 (CH 2 ) 3 CH 2 -, -CH 2 CH 2 0CH 2 CH 2 -, -CH 2 CH(Me)CH 2 CH(Me)CH 2 -, or -CH 2 CH(Me)OCH(Me)CH 2 -; and R 13 is halogen; C 1 -C alkyl, C-*_-C alkoxy, or C*L-C 4 haloalkyl; provided that: i) when Z is CR 5 =CR 6 , then at least one substituent selected from the group consisting of R 3 , R 4 , R 5 and R 6 , is hydrogen; and ii) the total number of carbons in R 3 , R 4 , R 5 and R 6 is equal to or less than 16; iϋ) the total number of nitrogen atoms incorporated into the bicyclic framework is less than or equal to four; iv) R 3 and R 4 are not both hydrogen; and v) X and Y are not both nitrogen. N-oxides and agriculturally suitable salts thereof. 2. A compound of Claim 1 wherein: W is 0; S; ΝH; or ΝR 9 ; X is CR 3 ; Y is CR 4 ; R 1 is C**_-C 8 alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C 1 -C 8 haloalkyl; C 2 -C 8 haloalkenyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C -C 8 cycloalkylalkyl; C 2 -C 8 cyanoalkyl; C 1 -C 8 alkoxy; C 1 -C 18 haloalkoxy; C 3 -C 8 alkenyloxy; C 3 -C 8 alkenylthio; or C 4 -C 8 alkenyloxyalkyl; R 2 is C^Cg alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C- ] _-C 8 haloalkyl; C 2 -C 8 haloalkenyl; C -C 8 alkoxyalkyl; C -C 8 alkylthioalkyl; C -C 8 cycloalkylalkyl; C -C 8 cyanoalkyl; C 4 -C 8 alkenyloxyalkyl; or phenyl optionally substituted with R 13 ; and R 4 and R 6 are each independently hydrogen; halogen; C-* ^ -^ alkyl; C 3 -C 8 cycloalkyl; C^C Q haloalkyl; C 1 -C 8 alkoxy; C* j _-C 8 haloalkoxy; C^C β alkylthio; C--_-C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; or cyano. 3. A compound of Claim 2 wherein: Q is O; W is 0; S; NH; or NMe; Z is CR 5 =CR 6 ; CR 5 =N; S; or 0; R 1 is C- j^ -Cs alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C- j^ -Ce haloalkyl; C 2 -C 8 haloalkenyl; C- j _-C 8 alkoxy; C 2 -C 8 alkoxyalkyl; or C 3 -C 8 alkenyloxy; R 2 is C 1 -C 8 alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C* j _-C 8 haloalkyl; C 2 -C 8 haloalkenyl; C 2 -C 8 alkoxyalkyl; or phenyl optionally substituted with R 13 ; and R 4 and R 6 are each independently hydrogen; halogen; C**^^ alkyl; C- ] _-C 8 haloalkyl; C-L-C-3 alkoxy; C 1 -C 8 haloalkoxy; C 3 -C 8 trialkylsilyl; or cyano. 4. A compound of Claim 3 wherein: Z is CR 5 =CR 6 or S; R 1 is C x -C 8 alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C-*_-C 8 haloalkyl; or C -C 8 haloalkenyl; R 2 is C 1 -C 8 alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C-L-C*- } haloalkyl; C 2 -C 8 haloalkenyl; or phenyl optionally substituted with R 13 ; and R 4 and R 6 are each independently hydrogen; halogen; C x -C 8 alkyl; C-*_-C 8 haloalkyl; C 1 -C 8 alkoxy; or C-L-CS haloalkoxy. 5. A compound of Claim 4 which is 7-bromo-3-(n-propyl) -1- (n-propyloxy)-4H- pyrido[1,2-a]pyrimidin-4-one; 7, 9-dibromo-3- (n-propyl) -2-(n-propyloxy) -4H- pyrido[1,2-a]pyrimidin-4-one; or 7-iodo-3- (n-propyl)-2- (n-propyloxy) -4H- pyrido[1,2-a]pyrimidin-4-one. 6. A fungicidal composition comprising an effective amount of a compound of Formula I wherein: Q is 0 or S; W is 0; S; S(O) ; S(0) 2 ; NH; or NR 9 ; X is CR 3 or N; Y is CR 4 or N; Z is CR 5 =CR 6 ; CR 5 =N; N=CR 6 ; S; 0; or NR 7 ; having the directionality of the CR 5 =CR 6 , CR 5 =N and N=CR 6 linkages such that the moiety depicted on the left side of the double bond is bonded to Y and the moiety on the right side of the double bond is bonded to the ring junction; R 1 is C 1 -C 18 alkyl; C 3 -C 7 cycloalkyl; C 2 -C 18 alkenyl; C 2 -C 18 alkynyl; C 1 -C 18 haloalkyl; C 2 -C 18 haloalkenyl; C 2 -C 18 haloalkynyl; C 2 -C 18 alkoxyalkyl; C -C 18 alkylthioalkyl; C 2 -C 18 alkylsulfinylalkyl; C 2 -C 18 alkylsulfonylalkyl; C 4 -C 18 cycloalkylalkyl; C 4 -C 18 alkenyloxyalkyl; C 4 -C 18 alkynyloxyalkyl; C -C 18 cycloalkyloxy- alkyl; C -C 18 alkenylthioalkyl; C -C 18 alkynylthioalkyl; Cg-C 18 cycloalkylthioalkyl; C 2 -C 18 haloalkoxyalkyl; C 3 -C 18 haloalkenyloxy- alkyl; C -C 18 haloalkynyloxyalkyl; C -C 18 alkoxyalkenyl; C -C 18 alkoxyalkynyl; C 4 -C 18 alkylthioalkenyl; C 4 -C 18 alkylthioalkynyl; c 4 ~ c i8 trialkylsilylalkyl; C-^C**^ alkyl substituted with NR 8 R 10 , cyano, or nitro; C -C Q alkyl substituted with C0 2 R 8 ; C^C- j ^ alkoxy; C 1 ~ C 18 haloalkoxy; C 3 -C 18 alkynyloxy; C 3 -C 18 alkenyloxy; C χ -C 18 alkylthio; C 3 -C 18 alkenyl- thio; or C 3 -C 18 alkynylthio; R 2 is alkyl; C 3 -C 7 cycloalkyl; C 3 -C 18 alkenyl; C 3 -C 18 alkynyl; C^C*-^ haloalkyl; C 3 -C 18 haloalkenyl; C 3 -C 18 haloalkynyl; C 2 -C 18 alkoxyalkyl; C 2 -C 18 alkylthioalkyl; C 2 -C 18 alkylsulfinylalkyl; C 2 -C 18 alkylsulfonylalkyl; C 4 -C 18 cycloalkylalkyl; C 4 -C 18 alkenyloxyalkyl; C 4 -C 18 alkynyloxyalkyl; C 4 -C 18 cycloalkyloxy- alkyl; C 4 -C 18 alkenylthioalkyl; C -C 18 alkynyl¬ thioalkyl; C 6 -C 18 cycloalkylthioalkyl; C -C 18 haloalkoxyalkyl; C 3 -C 18 haloalkenyloxyalkyl; C 4 -C 18 haloalkynyloxyalkyl; C 4 -C 18 alkoxy- alkenyl; C 4 -C 18 alkoxyalkynyl; C 4 -C 18 alkylthio- alkenyl; C 4 -C 18 alkylthioalkynyl; C 4 -C 18 trialkylsilylalkyl; C* j _-C 18 alkyl substituted with NR 8 R 10 ; C 2 -C 18 cyanoalkyl; C 2 -C 18 nitro- alkyl; C 1 -C 8 alkyl substituted with C0 2 R 8 ; or phenyl, benzyl, or phenethyl each optionally substituted on the phenyl ring with R 13 ; or R 1 and R 2 can be taken together along with the C=C-W fragment to which they are attached to form a 5-7 membered ring in which the R^—R 2 bridge is a saturated, all-carbon chain optionally substituted with C 1 -C 12 alkyl; R 3 and R 5 are each independently hydrogen; halogen; C 1 -C 4 alkyl; C x -C haloalkyl; C x -C 4 alkoxy; or c ι~ c 4 haloalkoxy; R 4 and R 6 are each independently hydrogen; halogen; C x -C 8 alkyl; C 3 -C 8 cycloalkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C x -C 8 haloalkyl; C 3 -C 8 halo¬ alkenyl; C 3 -C 8 haloalkynyl; C±-Cg alkoxy; C-L-CS haloalkoxy; C 3 -C 8 alkenyloxy; C 3 -C 8 alkynyloxy; c l ~ c 8 alkylthio; C 3 -C 8 alkenylthio; C 3 -C 8 alkynylthio; C_ -C Q alkylsulfinyl; C x -C 8 alkyl- sulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthio¬ alkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkyl- sulfonylalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; cyano; nitro; C0 2 Me; C0 2 Et; or JJR11R12. R 7 is C x -C 4 alkyl or C- ] _-C 4 haloalkyl; R 8 and R 9 are each independently C 2 -C 4 alkyl; R 10 and R 11 are each independently H or C 1 -C alkyl; R 12 is C x -C 8 alkyl; R 8 and R 10 or the groups R 11 and R 12 , can be taken together to form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 (CH 2 ) 3 CH 2 -, -CH 2 CH 2 OCH 2 CH 2 -, -CH 2 CH(Me)CH 2 CH(Me)CH 2 -, or -CH 2 CH(Me)OCH(Me)CH 2 -; and R 13 is halogen; C 1 -C alkyl, C-*_-C 4 alkoxy, or C* j _-C 4 haloalkyl; provided that: i) when Z is CR 5 =CR 6 , then at least one substituent selected from the group consisting of R 3 , R 4 , R 5 and R 6 , is hydrogen; and ii) the total number of carbons in R 3 , R 4 , R 5 and R 6 is equal to or less than 16; iϋ) the total number of nitrogen atoms incorporated into the bicyclic framework is less than or equal to four; iv) R 3 and R 4 are not both hydrogen; and v) X and Y are not both nitrogen; and at least one of (a) a surfactant, (b) an organic solvent, and (c) at least one solid or liquid diluent. 7. A method for controlling plant diseases caused _ by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, to the media in which the plant to be protected is growing, or to the plant seed or seedling to be protected an effective amount of a compound of Formula I wherein: Q is 0 or S; W is 0; S; S (0) ; S(0) 2 ; NH; or NR 9 ; X is CR 3 or N; Y is CR 4 or N; Z is CR 5 =CR 6 ; CR 5 =N; N=CR 6 ; S; O; or NR 7 ; having the directionality of the CR 5 =CR 6 , CR 5 =N and N=CR 6 linkages such that the moiety depicted on the left side of the double bond is bonded to Y and the moiety on the right side of the double bond is bonded to the ring junction; R 1 is C x -C 18 alkyl; C 3 -C 7 cycloalkyl; C 2 -C 18 alkenyl; C 2 -C 18 alkynyl; C-L-C-*^ haloalkyl; C 2 -C 18 haloalkenyl; C 2 -C 18 haloalkynyl; C 2 -C 18 alkoxyalkyl; C 2 -C 18 alkylthioalkyl; C 2 -C 18 alkylsulfinylalkyl; C 2 -C 18 alkylsulfonylalkyl; C 4 -C 18 cycloalkylalkyl; C 4 -C 18 alkenyloxyalkyl; C 4 -C 18 alkynyloxyalkyl; C 4 -C 18 cycloalkyloxy- alkyl; C -C 18 alkenylthioalkyl; C 4 -C 18 alkynyl- thioalkyl; C e -C 18 cycloalkylthioalkyl; C 2 -C 18 haloalkoxyalkyl; C 3 -C 18 haloalkenyloxyalkyl; C -C 18 haloalkynyloxyalkyl; C 4 -C 18 alkoxy- alkenyl; C 4 -C 18 alkoxyalkynyl; C 4 -C 18 alkylthio- alkenyl; C -C 18 alkylthioalkynyl; C -C 18 trialkylsilylalkyl; C^C***^ alkyl substituted with NR 8 R 10 , cyano, or nitro; C 1 -C 8 alkyl substituted with C0 2 R 8 ; Cι-C 18 alkoxy; C±-C 18 haloalkoxy; C 3 -C 18 alkynyloxy; C 3 -C 18 alkenyl¬ oxy; C 1 -C 18 alkylthio; C 3 -C 18 alkenylthio; or c 3 -c i 8 alkynylthio; R 2 is C-L-C-LS alkyl; C 3 -C 7 cycloalkyl; C 3 -C 18 alkenyl; C 3 -C 18 alkynyl; C 1 -C 18 haloalkyl; C 3 -C 18 haloalkenyl; C 3 -C 18 haloalkynyl; C 2 -C 18 alkoxyalkyl; C 2 -C 18 alkylthioalkyl; C 2 -C 18 alkylsulfinylalkyl; C 2 -C 18 alkylsulfonylalkyl; C 4 -C 18 cycloalkylalkyl; C 4 -C 18 alkenyloxyalkyl; C 4 -C 18 alkynyloxyalkyl; C 4 -C 18 cycloalkyloxy- alkyl; C 4 -C 18 alkenylthioalkyl; C 4 -C 18 alkynyl¬ thioalkyl; C 6 -C 18 cycloalkylthioalkyl; C 2 -C 18 haloalkoxyalkyl; C 3 -C 18 haloalkenyloxyalkyl; C -C 18 haloalkynyloxyalkyl; C 4 -C 18 alkoxy- ' alkenyl; C 4 -C 18 alkoxyalkynyl; C 4 -C 18 alkyl- thioalkenyl; C 4 -C 18 alkylthioalkynyl; C -C 18 " trialkylsilylalkyl; C 1 -C 18 alkyl substituted with NR 8 R 10 ; C 2 -C 18 cyanoalkyl; C 2 -C 18 nitroalkyl; C ± -C Q alkyl substituted with C0 2 R 8 ; or phenyl, benzyl, or phenethyl each optionally substituted on the phenyl ring with R 13 ; or R 1 and R 2 can be taken together along with the C=C-W fragment to which they are attached to form a 5-7 membered ring in which the R 1 -R 2 bridge is a saturated, all-carbon chain optionally substituted with C 1 -C 12 alkyl; R 3 and R 5 are each independently hydrogen; halogen; C 1 -C 4 alkyl; C x -C haloalkyl; C 1 -C alkoxy; or c ι -c 4 haloalkoxy; R 4 and R 6 are each independently hydrogen; halogen; C 1 -C 8 alkyl; C 3 -C 8 cycloalkyl; C -C 8 alkenyl; C 2 -C 8 alkynyl; C**_-C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 haloalkynyl; C^-^ alkoxy; C . ι.-C 8 haloalkoxy; C 3 -C 8 alkenyloxy; C 3 -C 8 alkynyloxy; C-^-^ alkylthio; C 3 -C 8 alkenylthio; C 3 -C 8 alkynylthio; C**_-C 8 alkylsulfinyl; C- j^ -Cs alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkylsulfonylalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; cyano; nitro; C0 2 Me; C0 2 Et; or NR 1:L R 12 ; R 7 is C* j _-C alkyl or C**_-C 4 haloalkyl; R 8 and R 9 are each independently alkyl; R 10 and R 11 are each independently H or C 1 -C 4 alkyl; R 12 is C 1 -C 8 alkyl; R 8 and R 10 , or the groups R 11 and R 12 , can be taken together to form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 (CH 2 ) 3 CH 2 -, -CH 2 CH 2 OCH 2 CH 2 -, -CH 2 CH(Me) CH 2 CH(Me)CH 2 -, or -CH 2 CH(Me)OCH(Me)CH 2 -; and R 13 is halogen; C_-C alkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkyl; provided that: i) when Z is CR 5 =CR 6 , then at least one substituent selected from the group consisting of R 3 , R 4 , R 5 and R 6 , is hydrogen; and ii) the total number of carbons in R 3 , R 4 , R 5 and R 6 is equal to or less than 16; iϋ) the total number of nitrogen atoms incorporated into the bicyclic framework is less than or equal to four; iv) R 3 and R 4 are not both hydrogen; and v) X and Y are not both nitrogen; or N-oxides or agriculturally suitable salts thereof. 8. A method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, to the media in which the plant to be protected is growing, or to the plant seed or seedling to be protected an effective amount of a composition of Claim 6. 9. A method for controlling wheat powdery mildew comprising applying to the plant or portion thereof to be protected, to the media in which the plant to be protected is growing, or to the plant seed or seedling to be protected an effective amount of a compound of Claim 1. 10. A method for controlling wheat powdery mildew comprising applying to the plant or portion thereof to be protected, to the media in which the plant to be protected is growing, or to the plant seed or seedling to be protected an effective amount of a composition of Claim 6.

Inventors: SELBY THOMAS PAUL, SELBY, THOMAS, PAUL
Applicants: DU PONT, SELBY THOMAS PAUL, E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1993
Main classification: C07D471
IPC codes: C07D471, C07D491, C07D513