TITLE ARTHROPODICIDAL AND FUNGICIDAL CYCLIC AMIDES BACKGROUND OF THE INVENTION This invention relates to certain cyclic amides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides and arthropodicides.

The control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumers. The control of arthropod pests is also extremely important in achieving high crop efficiency. Arthropod damage to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of arthropod pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes; but the need continues for new compound.', which are more effective, less costly, less toxic, environmentally safer or have different modes of action.

WO 95/14009 discloses cyclic amides of Formula i as fungicides: wherein A is O; S; N; NR5; or CR14; G is C or N; provided that when G is C, A is O, S or NR5 and the floating double bond is attached to G; and when G is N, A is N or CR14 and the floating double bond is attached to A; W is O or S; Xis OR1; S(O)mRl; or halogen; R1, R2, and R5 are each independently, in part, H or C1-C6 alkyl;

R3 and R4 are each independently, in part, H; halogen; cyano; nitro; Cl-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; or C1-C6 haloalkoxy; Y is, in part, -0-; -CR6=CR6-; -C-C-; -CHR6O-; -OCHR6-; -CHR6O-N=C(R7)-; -(R7)C=N-OCH(R6)-; -C(R7)=N-o-; -O-N=C(R7)-; or a direct bond; R6 is independently H or C1-C3 alkyl; R7 is, in part, H; C1-C6 alkyl; C1-C6 haloalkyl; or C1-C6 alkoxy; Z is, in part, an optionally substituted phenyl, 3 to 14-membered nonaromatic heterocyclic ring system or 5 to 14-membered aromatic heterocyclic ring system; R14 is H; halogen; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; or C3-C6 cycloalkyl; and m is O, 1 or 2.

This publication does not disclose use of the compounds as arthropodicides.

Furthermore, this publication does not disclose compounds where the optional substituents on Z are themselves substituted with C2-C6 alkenyl, C2-C6 haloalkenyl C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C1-C4 alkylthio, C1-C4 haloalkylthio, Cl-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C3-C6 alkenylthio, C3-C6 haloalkenylthio, or SFg.

SUMMARY OF THE INVENTION This invention involves compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof: wherein E is selected from: i) 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; ii) a naphthalene ring, provided that when G and Y are attached to the same ring, then G and Y are attached to adjacent ring members, the naphthalene ring optionally substituted with one of R3, R4, or both R3 and R4; and iii) a ring system selected from 5 to 1 2-membered monocyclic and fused

bicyclic aromatic heterocyclic ring systems, each heterocyclic ring system containing 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs, each fused bicyclic ring system optionally containing one nonaromatic ring that optionally includes one or two Q as ring members and optionally includes one or two ring members independently selected from C(=O) and S(O)2, provided that G is attached to an aromatic ring, and when G and Y are attached to the same ring, then G and Y are attached to adjacent ring members, each aromatic heterocyclic ring system optionally substituted with one of R3, R4, or both R3 and R4; A is O; S; N; NR5; or CR14; G is C or N; provided that when G is C, then A is O, S or NR5 and the floating double bond is attached to G; and when G is N, then A is N or CR14 and the floating double bond is attached to A; W is O; S; NH; N(C1-C6 alkyl); or NO(C1-C6 alkyl); X is H; OR1; S(O)mR1; halogen; C1-C6 alkyl; C1-C6 haloalkyl; C3-C6 cycloalkyl; cyano; NH2; NHR1; N(C1-C6 alkyl)R1; NH(C1-C6 alkoxy); or N(C1-C6 alkoxy)Rl; R1 is C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; R2 is H; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; hydroxy; C1-C2 alkoxy; or acetyloxy; R3 and R4 are each independently halogen; cyano; nitro; hydroxy; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C2-C6 alkenyloxy; C2-C6 alkynyloxy; C1-C6 alkylthio; C1-C6 alkylsulfinyl; Cl-C6 alkylsulfonyl; formyl; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; NH2C(O); (C1-C4 alkyl)NHC(O); (C1-C4 alkyl)2NC(O); Si(R25)3; Ge(R25)3; (R25)3Si-C-C-; or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R8 and optionally substituted with one or more R10; or when E is 1,2-phenylene and R3 and R4 are attached to adjacent atoms, R3 and R4 can be taken together as C3-C5 alkylene, C3-C5 haloalkylene, C3-Cs

alkenylene or C3-C5 haloalkenylene each optionally substituted with 1-2 C1-C3 alkyl; Rs is H; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; Y is -O-; -S(O)n-; -NR15-; -C(=O)-; -CH(OR15)-; -CHR6-; -CHR6CHR6-; -CR6=CR6-; -C#C-; -CHR15O-; -OCHR15-; -CHR15S(O)n-; -S(O)nCHR15-; -CHR15O-N=C(R7)-; -(R7)C=N-OCH(R15)-; -C(R7)=N-O-; -O-N=C(R7)-; -CHR1 5OC(=o)N(R1 5)-; -CHR1 5OC(=S)N(R1 5); -CHR 5OC(=O)O-; -CHR1 5OC(=S)O-; -CHR1 5OC(=O)S-; -CHR1 5OC(=S)S-; -CHR15SC(=O)N(R15)-; -CHR15SC(=S)N(R15)-; -CHR15SC(=O)O-; -CHR15SC(=S)O-; -CHR15SC(=O)S-; -CHR15SC(=S)S-; -CHR15SC(=NR15)S-; -CHR15N(R15)C(=O)N(R15)-; -CHR15O-N(R15)C(=O)N(R15)-; -CHR15O-N(R15)C(=S)N(R15)-; -CHR15O-N=C(R7)NR15-; -CHR15O-N=C(R7)OCH2-; -CHR15O-N=C(R7)N=N-; -CHR15O-N=C(R7)-C(=O)-; -CHR15O-N=C(R7)-C(=N-A²-Z )-A -; -CHR150-N=C(R7)-C(R7)=N-A2-A3-; -CHR1 5O-N=C(-C(R7)=N-A²-Z )-; -CHR15O-N=C(R7)-CH2O-; -CHR15O-N=C(R7)-CH2S-; -O-CH2CH2O-N=C(R7)-; -CHR1 5O-C(R1 5)=C(R7)-; -CHR1 5O-C(R7)=N-; -CHR15S-C(R7)=N-; -C(R7)=N-NR15-; -CH=N-N=C(R7)-; -CHR15N(R15)-N=C(R7)-; -CHR15N(COCH3)-N=C(R7)-; -OC(=S)NR15C(=O)-; -CHR6-C(=W )-A -; -CHR6CHR6-C(=W )-A -; -CR6=CR6-C(=W )-A -; -C#C-C(=W )-A -; -N=CR6-C(=W )-A -; or a direct bond; and the directionality of the Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to E and the moiety on the right side of the linkage is bonded to Z; Z1 is H or -A3-Z; W1 isOorS; A1 is O; S; NR15; or a direct bond; A2 is O; NR15; or a direct bond; A3 is -C(=O)-; -S(O)2-; or a direct bond; each R6 is independently H; 1-2 CH3; C2-C3 alkyl; C1-C3 alkoxy; C3-C6 cycloalkyl; formylamino; C2-C4 alkylcarbonylamino; C2-C4 alkoxycarbonylamino; NH2C(O)NH; (C1-C3 alkyl)NHC(O)NH;

(C1-C3 alkyl)2NC(O)NH; N(CI-C3 alkyl)2; piperidinyl; morpholinyl; 1-2 halogen; cyano; or nitro; each R7 is independently H; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; Cl-C6 haloalkoxy; C1-C6 alkylthio; C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; C1-C6 haloalkylthio; C1-C6 haloalkylsulfinyl; C1-C6 haloalkylsulfonyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy; amino; NH(C1-C6 alkyl); N(C1-C6 alkyl)2; or morpholinyl; each Z is independently selected from: i) C1-Cl0 alkyl, C2-C10 alkenyl, and C2-C10 alkynyl each substituted with R9 and optionally substituted with one or more R10; ii) C3-C8 cycloalkyl, C3-C8 cycloalkenyl and phenyl each substituted with R9 and optionally substituted with one or more R10; iii) a ring system selected from 3 to 14-membered monocyclic, fused bicyclic and fused tricyclic nonaromatic heterocyclic ring systems and 5 to 14-membered monocyclic, fused bicyclic and fused tricyclic aromatic heterocyclic ring systems, each heterocyclic ring system containing 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs, each nonaromatic or aromatic heterocyclic ring system substituted with R9 and optionally substituted with one or more R10; iv) a multicyclic ring system selected from 8 to 14-membered fused-bicyclic and fused-tricyclic ring systems which are an aromatic carbocyclic ring system, a nonaromatic carbocyclic ring system, or a ring system containing one or two nonaromatic rings that each include one or two Q as ring members and one or two ring members independently selected from C(=O) and S(0)2, and any remaining rings as aromatic carbocyclic rings, each multicyclic ring system substituted with R9 and optionally substituted with one or more R10; and v) adamantyl substituted with R9 and optionally substituted with one or more R10; each Q is independently selected from the group -CHR13-, -NR13-, -O-, and -S(O)p-; R8 is H; 1-2 halogen; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C1-C6

alkylthio; C1-C6 haloalkylthio; C1-C6 alkylsulfinyl; Cl-C6 alkylsulfonyl; C3-C6 cycloalkyl; C3-C6 alkenyloxy; CO2(CI-C6 alkyl); NH(CI-C6 alkyl); N(C1-C6 alkyl)2; cyano; nitro; SiR19R20R21; or GeR19R20R21; R9 is H; 1-2 halogen; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C1-C6 alkylthio; C1-C6 haloalkylthio; C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; C3-C6 cycloalkyl; C3-C6 alkenyloxy; CO2(C1-C6 alkyl); NH(C1-C6 alkyl); N(C1-C6 alkyl)2; -C(R18)=NOR17; cyano; nitro; SF5; SiR22R23R24; or GeR22R23R24; or R9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R11, R12, or both R11 and R12; each R10 is independently halogen; Cl-C4 alkyl; C1-C4 haloalkyl; Cl-C4 alkoxy; nitro; or cyano; or when R9 and an R10 are attached to adjacent atoms on Z, R9 and said adjacently attached R10 can be taken together as -OCH2O- or -OCH2CH2O-; each CH2 group of said taken together R9 and R10 optionally substituted with 1-2 halogen; or when Y and an R10 are attached to adjacent atoms on Z and Y is -CHR15O-N=C(R7)-, -O-N=C(R7)-, -O-CH2CH2O-N=C(R7)-, -CHR15O-C(R15)=C(R7)-, -CH=N-N=C(R7)-, -CHR1 sN(R l 5)-N=C(R7)- or -CHR15N(COCH3)-N=C(R7)-, R7 and said adjacently attached R10 can be taken together as -(CH2)r-J- such that J is attached to Z; J is -CH2-; -CH2CH2-; -OCH2-; -CH2O-; -SCH2-; -CH2S-; -N(R16)CH2-; or -CH2N(R16)-; each CH2 group of said J optionally substituted with 1 to 2 CH3; R11 and R12 are each independently 1-2 halogen; C1-C4 alkyl; C1-C4 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C2-C6 alkoxyalkyl; C2-C6 alkylthioalkyl; C3-C6 alkoxyalkynyl; C7-C10 tetrahydropyranyloxyalkynyl; benzyloxymethyl; Cl-C4 alkoxy; Cl-C4 haloalkoxy; C3-C6 alkenyloxy; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy; C3-C6 haloalkynyloxy; C2-C6 alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; Cl-C4 alkylthio; Cl-C4 haloalkylthio; C1-C4 alkylsulfinyl; C1-C4 haloalkylsulfinyl; C1-C4 alkylsulfonyl; C1-C4 haloalkylsulfonyl; C3-C6 alkenylthio; C3-C6 haloalkenylthio; C2-C6 alkylthioalkylthio; nitro; cyano; thiocyanato; hydroxy; N(R26)2; SF5; Si(R25)3; Ge(R25)3; (R25)3Si-C=-C-; OSi(R25)3; OGe(R25)3; C(=O)R26;

C(=S)R26; C(=O)OR26; C(=S)OR26; C(=O)SR26; C(=S)SR26; C(=O)N(R26)2; C(=S)N(R26)2; OC(=O)R26; OC(=S)R26; SC(=O)R26; SC(=S)R26; N(R26)C(=O)R26; N(R26)C(=S)R26; OC(=O)OR27; OC(=O)SR27; OC(=O)N(R26)2; SC(=O)OR27; SC(=O)SR27; 5(0) 2OR26; S(O)2N(R26)2; OS(O)2R27; N(R26)S(O)2R27; or phenyl, phenoxy, benzyl, benzyloxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, Cl-C4 haloalkoxy, nitro or cyano; each R13 is independently H; C1-C6 alkyl; C1-C6 haloalkyl; or phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, Cl-C4 haloalkoxy, nitro or cyano; R14 is H; halogen; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; or C3-C6 cycloalkyl; each R15 is independently H; C1-C3 alkyl; C3-C6 cycloalkyl; or phenyl or benzyl each optionally substituted on the phenyl ring with halogen, C1-C4 alkyl C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; or when Y is -CHR15N(R15)C(=O)N(R15)-, the two R15 attached to nitrogen atoms on said group can be taken together as -(CH2)s-; or when Y is -CHR15O-N=C(R7)NR15-, R7 and the adjacently attached R15 can be taken together as -CH2-(CH2)S-; -O-(CH2)5-; -S-(CH2)5-; or -N(C1-C3 alkyl)-(CH2)s-; with the directionality of said linkage defined such that the moiety depicted on the left side of the linkage is bonded to the carbon and the moiety on the right side of the linkage is bonded to the nitrogen; R16, R17, and R18 are each independently H; C1-C3 alkyl; C3-C6 cycloalkyl; or phenyl optionally substituted with halogen, C1-C4 alkyl, Cl-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; R19, R20, R21, R22, R23, and R24 are each independently C1-C6 alkyl; C2-C6 alkenyl; C1-C4 alkoxy; or phenyl; each R25 is independently C1-C4 alkyl; Cl-C4 haloalkyl; C2-C4 alkenyl; Cl-C4 alkoxy; or phenyl; each R26 is independently H; Cl-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C1 -C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano;

each R27 is independently C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C1 -C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; m, n and p are each independently 0, 1 or 2; risOor 1; and s is 2 or 3.

This invention provides a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, provided that: (i) when E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; Xis OR1, S(O)mR1 or halogen; Y is -O-, -S(O)n-, -NR15-, -C(=O)-,-CH(OR15)-, -CHR6-, -CHR6CHR6-, -CR6=CR6- -C=C-, -CHR15O-, -OCHR15-, -CHR15S(O)n-, -S(O)nCHR15-, -CHR15O-N=C(R7)-, -(R7)C=N-OCH(R15)-, -C(R7)=N-O-, -O-N=C(R7)-, -CHR15OC(=O)N(R15)- or a direct bond; and R9 is SiR22R23R24 or GeR22R23R24; then Z is other than phenyl or a 5 to 14-membered aromatic heterocyclic ring system each substituted with R9 and optionally substituted with one or more R10; (ii) when E is a naphthalene ring optionally substituted with one of R3, R4, or both R3 and R4; R3 or R4 is Si(R25)3 or Ge(R25)3; and Y is -O-, -S(O)n-, -C(=O)-, -CHR6-, -CHR6CHR6-, -CR6=CR6-, -C-C-, -OCHR15-, -S(O)nCHR15- or a direct bond; then Z is other than C1-Cl0 alkyl, C2-C10 alkenyl or C2-C10 alkynyl each substituted with R9 and optionally substituted with one or more R10; and (iii) when E is a naphthalene ring optionally substituted with one of R3, R4, or both R3 and R4; R3 or R4 is Si(R25)3 or Ge(R25)3; and Y is -8(0)n-, -C(=O)-, -C-C- or a direct bond; then Z is other than phenyl substituted with R9 and optionally substituted with one or more R10.

This invention also provides selected compounds of Formula I which are considered particularly effective fungicides and arthropodicides. Specifically, this invention provides compounds of Formula IA including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, and agricultural compositions containing them and their use as fungicides and arthropodicides:

wherein E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; Ais OorN; G is C or N; provided that when G is C, then A is 0 and the floating double bond is attached to G; and when G is N, then A is N and the floating double bond is attached to A; <BR> <BR> <BR> WisO; <BR> <BR> <BR> <BR> <BR> Xis OR1; R1 is C1-C3 alkyl; R2 is H or C1-C2 alkyl; R3 and R4 are each independently halogen; cyano; nitro; hydroxy; Cl-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C2-C6 alkenyloxy; C2-C6 alkynyloxy; C1-C6 alkylthio; C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; formyl; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; NHC(O); (C1-C4 alkyl)NHC(O); (C1-C4 alkyl)2NC(O); Si(R25)3; Ge(R25)3; (R25)3Si-C=-C-; or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R8 and optionally substituted with one or more R10; Y is -O-; -S(O)n-; -NR15-; -C(=O)-; -CH(OR1 5)-; -CH2-; -CH2CH2-; -CH=CH-; -C-C-; -CH2O-; -OCH2-; -CH2S(O)n-; -S(O)nCH2-; or a direct bond; and the directionality of the Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to E and the moiety on the right side of the linkage is bonded to Z; Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,4-thiadiazolyl; 1,3,4-thiadiazolyl; and pyrazinyl; each group substituted with R9 and optionally substituted with one or more R10; R9 is H; halogen; C1-C6 alkyl; C1-C6 haloalkyl; Cl-C6 alkoxy; C1-C6 haloalkoxy; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C1-C6 alkylthio; C1-C6 haloalkylthio; C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; C3-C6 cycloalkyl; C3-C6 alkenyloxy; CO2(CI-C6 alkyl); NH(CI-C6 alkyl); N(C1-C6 alkyl)2;

-C(R18)=NOR17; cyano; nitro; SFg; SiR22R23R24; or GeR22R23R24; or R9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R11, R12 or both R11 and R12; provided that when Z is pyrazinyl, then R9 is other than H or C1-C6 haloalkyl; each R10 is independently halogen; C1-C4 alkyl; C1-C4 haloalkyl; Cl-C4 alkoxy; nitro; or cyano; or when R9 and an R10 are attached to adjacent atoms on Z, R9 and said adjacently attached R10 can be taken together as -OCH2O- or -OCH2CH2O-; each CH2 group of said taken together R9 and R10 optionally substituted with 1-2 halogen; R11 and R12 are each independently 1-2 halogen; C1-C4 alkyl; C1-C4 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C2-C6 alkoxyalkyl; C2-C6 alkylthioalkyl; C3-C6 alkoxyalkynyl; C7-C10 tetrahydropyranyloxyalkynyl; benzyloxymethyl; Cl-C4 alkoxy; Cl-C4 haloalkoxy; C3-C6 alkenyloxy; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy; C3-C6 haloalkynyloxy; C2-C6 alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; C1-C4 alkylthio; C1-C4 haloalkylthio; C1-C4 alkylsulfinyl; C1 -C4 haloalkylsulfinyl; C1 -C4 alkylsulfonyl; Cl-C4 haloalkylsulfonyl; C3-C6 alkenylthio; C3-C6 haloalkenylthio; C2-C6 alkylthioalkylthio; nitro; cyano; thiocyanato; hydroxy; N(R26)2; SF5; Si(R25)3; Ge(R25)3; (R25)3Si-C=-C-; OSi(R25)3; OGe(R25)3; C(=O)R26; C(=S)R26; C(=0)OR26; C(=S)OR26; C(=O)SR26; C(=S)SR26; C(=O)N(R26)2; C(=S)N(R26)2; OC(=O)R26; OC(=S)R26; SC(=O)R26; SC(=S)R26; N(R26)C(=O)R26; N(R26)C(=S)R26; OC(=0)0R27; OC(=O)SR27; oC(=O)N(R26)2; SC(=O)OR27; SC(=o)SR27; S(0)20R26; S(O)2N(R26)2; OS(O)2R27; N(R26)S(O)2R27; or phenyl, phenoxy, benzyl, benzyloxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, Cl-C4 haloalkoxy, nitro or cyano; R15 is H; C1-C3 alkyl; or cyclopropyl; R17 and R18 are each independently H; C1-C3 alkyl; C3-C6 cycloalkyl; or phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; R22, R23, and R24 are each independently C1-C6 alkyl; C2-C6 alkenyl; Cl-C4 alkoxy; or phenyl;

each R25 is independently Cl-C4 alkyl; Cl-C4 haloalkyl; C2-C4 alkenyl; C1-C4 alkoxy; or phenyl; each R26 is independently H; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C1 -C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; each R27 is independently C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C1 -C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, Cl-C4 haloalkoxy, nitro or cyano; and nisO, 1 or2.

This invention also provides certain compounds of Formula I which are useful as fungicides and arthropodicides. Specifically this invention provides compounds of Formula IB including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, and agricultural compositions containing them and their use as fungicides and arthropodicides: wherein E is selected from: i) 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; ii) a naphthalene ring, provided that when G and Y are attached to the same ring, then G and Y are attached to adjacent ring members, the naphthalene ring optionally substituted with one of R3, R4, or both R3 and R4; and iii) a ring system selected from 5 to 12-membered monocyclic and fused bicyclic aromatic heterocyclic ring systems, each heterocyclic ring system containing 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs, each fused bicyclic ring system optionally containing one

nonaromatic ring that optionally includes one or two Q as ring members and optionally includes one or two ring members independently selected from C(=O) and S(0)2, provided that G is attached to an aromatic ring, and when G and Y are attached to the same ring, then G and Y are attached to adjacent ring members, each aromatic heterocyclic ring system optionally substituted with one of R3, R4, or both R3 and R4; A is O; S; N; NR5; or CR14; G is C or N; provided that when G is C, then A is O, S or NR5 and the floating double bond is attached to G; and when G is N, then A is N or CR14 and the floating double bond is attached to A; W is O; S; NH; N(C1-C6 alkyl); or NO(C1-C6 alkyl); X is H; OR1; S(O)mR1; halogen; C1-C6 alkyl; C1-C6 haloalkyl; C3-C6 cycloalkyl: cyano; NH2; NHRl; N(C1-C6 alkyl)R1; NH(CI-C6 alkoxy); or N(C1-C6 alkoxy)Rl; R1 is C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; R2 is H; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; hydroxy; C1 -C2 alkoxy; or acetyloxy; R3 and R4 are each independently halogen; cyano; nitro; hydroxy; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C2-C6 alkenyloxy; C2-C6 alkynyloxy; C1-C6 alkylthio; C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; formyl; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; NH2C(O); (C1-C4 alkyl)NHC(O); (C1-C4 alkyl)2NC(O); Si(R25)3; Ge(R25)3; (R25)3Si-C=-C-; or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R8 and optionally substituted with one or more R10; or when E is 1,2-phenylene and R3 and R4 are attached to adjacent atoms, R3 and R4 can be taken together as C3-C5 alkylene, C3-C5 haloalkylene, C3-C5 alkenylene or C3-C5 haloalkenylene each optionally substituted with 1-2 C1-C3 alkyl; Rs is H; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl;

Y is -0-; -S(O)n-; -NR15-; -C(=0)-; -CH(ORl5)-; -CHR6-; -CHR6CHR6-; -CR6=CR6-; -C#C-; -CHR15O-; -OCHR15-; -CHR15S(O)n-; -S(O)nCHR15-; -CHR15O-N=C(R7)-; -(R7)C=N-OCH(R15)-; -C(R7)=N-O-; -O-N=C(R7)-; -CHR15OC(=O)N(R15)-; -CHR15OC(=S)N(R15); -CHR15OC(=O)O-; -CHR15OC(=S)O-; -CHR15OC(=O)S-; -CHR15OC(=S)S-; -CHR15SC(=O)N(R15)-; -CHR15SC(=S)N(R15)-; -CHR15SC(=O)O-; -CHR15SC(=S)O-; -CHR15SC(=O)S-; -CHR15SC(=S)S-; -CHR15SC(=NR15)S-; -CHR15N(R15)C(=O)N(R15)-; -CHR15O-N(R15)C(=O)N(R15)-; -CHR15O-N(R15)C(=S)N(R15)-; -CHR15O-N=C(R7)NR15-; -CHR15O-N=C(R7)OCH2-; -CHR15O-N=C(R7)-N=N-; -CHR15O-N=C(R7)-C(=O)-; -CHR15O-N=C(R7)-C(=N-A²-Z )-A -; -CHR15O-N=C(R7)-C(R7)=N-A²-A -; -CHR15O-N=C(-C(R7)=N-A²-Z )-; -CHR1 50-N=C(R7)-CH2O-; -CHR1 50-N=C(R7)-CH2S-; -O-CH2CH2O-N=C(R7)-; -CHR15O-C(R15)=C(R7)-; -CHR15O-C(R7)=N-, -CHR15S-C(R7)=N-; -C(R7)=N-NR15-; -CH=N-N=C(R7)-; -CHR15N(R15)-N=C(R7)-; -CHR15N(COCH3)-N=C(R7)-; -OC(=S)NR15C(=O)-; -CHR6-C(=W1 )-A1 -; -CHR6CHR6-C(=W1 )-A -, -CR6=CR6-C(=W )-A -; -C#C-C(=W )-A -; -N=CR6-C(=W1 )-A1 -; or a direct bond; and the directionality of the Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to E and the moiety on the right side of the linkage is bonded to Z; Z1 is H or -A3-Z; W is O or S; A1 is O; S; NR15; or a direct bond; A2 is O; NR15; or a direct bond; A3 is -C(=O)-; -S(O)2-; or a direct bond; each R6 is independently H; 1-2 CH3; C2-C3 alkyl; C1-C3 alkoxy; C3-C6 cycloalkyl; formylamino; C2-C4 alkylcarbonylamino; C2-C4 alkoxycarbonylamino; NH2C(O)NH; (C1 -C3 alkyl)NHC(O)NH; (C1-C3 alkyl)2NC(O)NH; N(CI-C3 alkyl)2; piperidinyl; morpholinyl; 1-2 halogen; cyano; or nitro; each R7 is independently H; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C1-C6 alkylthio; C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; C1-C6 haloalkylthio; C1-C6 haloalkylsulfinyl; C1-C6 haloalkylsulfonyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6

cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy; amino; NH(CI-C6 alkyl); N(CI-C6 alkyl)2; or morpholinyl; each Z is independently selected from: i) C1-Cl0 alkyl, C2-C10 alkenyl, or C2-C10 alkynyl each substituted with R9 and optionally substituted with one or more R10; ii) C3-C8 cycloalkyl, C3-C8 cycloalkenyl or phenyl each substituted with R9 and optionally substituted with one or more R10; iii) a ring system selected from 3 to 14-membered monocyclic, fused bicyclic and fused tricyclic nonaromatic heterocyclic ring systems and 5 to 14-membered monocyclic, fused bicyclic and fused tricyclic aromatic heterocyclic ring systems, each heterocyclic ring system containing 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs, each nonaromatic or aromatic heterocyclic ring system substituted with R9 and optionally substituted with one or more R10; iv) a multicyclic ring system selected from 8 to 14-membered fused-bicyclic and fused-tricyclic ring systems which are an aromatic carbocyclic ring system, a nonaromatic carbocyclic ring system, or a ring system containing one or two nonaromatic rings that each include one or two Q as ring members and one or two ring members independently selected from C(=O) and S(0)2, and any remaining rings as aromatic carbocyclic rings, each multicyclic ring system substituted with R9 and optionally substituted with one or more R10; and v) adamantyl substituted with R9 and optionally substituted with one or more Rio; each Q is independently selected from the group -CHR13-, -NR13-, -O-, and -S(O)p-; R8 is H; 1-2 halogen; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; Cl-C6 alkylthio; C1 -C6 haloalkylthio; C1-C6 alkylsulfinyl; Cl-C6 alkylsulfonyl; C3-C6 cycloalkyl; C3-C6 alkenyloxy; C02(CI-C6 alkyl); NH(CI-C6 alkyl); N(C1-C6 alkyl)2; cyano; nitro; SiR19R20R21; or GeR19R20R21; R9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy furanyl, pyrimidinyl, or pyrimidinyloxy each substituted with R1 1 and optionally substituted with R12;

each R10 is independently halogen; C1-C4 alkyl; C1-C4 haloalkyl; C1-C4 alkoxy; nitro; or cyano; or when R9 and an R10 are attached to adjacent atoms on Z, R9 and said adjacently attached R10 can be taken together as -OCH2O- or -OCH2CH2O-; each CH2 group of said taken together R9 and R10 optionally substituted with 1-2 halogen; or when Y and an R10 are attached to adjacent atoms on Z and Y is -CHR150-N=C(R7)-, -O-N=C(R7)-, -O-CH,CH20-N=C(R7)-, -CHR15O-C(R15)=C(R7)-, -CH=N-N=C(R7)-, -CHR15N(R15)-N=C(R7)- or -CHR15N(COCH3)-N=C(R7)-, R7 and said adjacently attached R10 can be taken together as -(CH2)r-J- such that J is attached to Z; J is -CH2-; -CH2CH2-; -OCH2-; -CH2O-; -SCH2-; -CH2S-; -N(R16)CH2-; or -CH2N(R16)-; each CH2 group of said J optionally substituted with 1 to 2 CH3; R11 is C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C2-C6 alkoxyalkyl; C2-C6 alkylthioalkyl; C3-C6 alkoxyalkynyl; C7-C10 tetrahydropyranyloxyalkynyl; benzyloxymethyl; C3-C6 alkenyloxy; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy; C3-C6 haloalkynyloxy; C2-C6 alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; Cl-C4 alkylthio; C1 -C4 haloalkylthio; C1 -C4 alkylsulfinyl; Cl-C4 haloalkylsulfinyl; Cl-C4 alkylsulfonyl; C1-C4 haloalkylsulfonyl; C3-C6 alkenylthio; C3-C6 haloalkenylthio; C2-C6 alkylthioalkylthio; thiocyanato; hydroxy; N(R26)2; SF5; (R25)3Si-C=C-; OSi(R25)3; OGe(R25)3; C(=O)R26; C(=S)R26; C(=O)OR26; C(=S)OR26; C(=O)SR26; C(=S)SR26; C(=O)N(R26)2; C(=S)N(R26)2; OC(=O)R26; OC(=S)R26; SC(=O)R26; SC(=S)R26; N(R26)C(=O)R26; N(R26)C(=S)R26; OC(=O)OR27; OC(=O)SR27; OC(=O)N(R26)2; SC(=o)oR27; SC(=0)SR27; S(0)20R26; S(O)2N(R26)2; OS(O)2R27; N(R26)S(O)2R27; or phenyl, phenoxy, benzyl, benzyloxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; R12 is 1-2 halogen; C1-C4 alkyl; C1-C4 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C2-C6 alkoxyalkyl; C2-C6 alkylthioalkyl; C3-C6 alkoxyalkynyl; C7-C10 tetrahydropyranyloxyalkynyl; benzyloxymethyl; C1-C4 alkoxy; Cl-C4 haloalkoxy; C3-C6 alkenyloxy; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy; C3-C6 haloalkynyloxy; C2-C6

alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; C1-C4 alkylthio; C1-C4 haloalkylthio; C1-C4 alkylsulfinyl; C1-C4 haloalkylsulfinyl; C1 -C4 alkylsulfonyl; C1 -C4 haloalkylsulfonyl; C3-C6 alkenylthio; C3-C6 haloalkenylthio; C2-C6 alkylthioalkylthio; nitro; cyano; thiocyanato; hydroxy; N(R26)2; SF5; Si(R25)3; Ge(R25)3; (R25)3Si-C=-C-; OSi(R25)3; OGe(R25)3; C(=O)R26; C(=S)R26; C(=O)OR26; C(=S)OR26; C(=O)SR26; C(=S)SR26; C(=O)N(R26)2; C(=S)N(R26)2; OC(=O)R26; OC(=S)R26; SC(=O)R26; SC(=S)R26; N(R26)C(=O)R26; N(R26)C(=S)R26; OC(=O)OR27; OC(=O)SR27; OC(=O)N(R26)2; SC(=O)0R27; SC(=o)SR27; S(0)20R26; S(O)2N(R26)2; oS(O)2R27; N(R26)S(0)2R27; or phenyl, phenoxy, benzyl, benzyloxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1 -C4 haloalkoxy, nitro or cyano; each R13 is independently H; C1-C6 alkyl; C1-C6 haloalkyl; or phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; R14 is H; halogen; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; or C3-C6 cycloalkyl; each R15 is independently H; C1-C3 alkyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C1 -C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; or when Y is -CHR15N(R15)C(=0)N(R15)-, the two R15 attached to nitrogen atoms on said group can be taken together as -(CH2)S-; or when Y is -CHR15O-N=C(R7)NR15-, R7 and the adjacently attached R15 can be taken together as -CH2-(CH2)s-; -0-(CH2)s-; -S-(CH2)s-; or -N(C1-C3 alkyl)-(CH2)s-; with the directionality of said linkage defined such that the moiety depicted on the left side of the linkage is bonded to the carbon and the moiety on the right side of the linkage is bonded to the nitrogen; R16 is H; C1-C3 alkyl; C3-C6 cycloalkyl; or phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; R19, R20, and R21 are each independently C1-C6 alkyl; C9-C6 alkenyl; C1-C4 alkoxy; or phenyl; each R25 is independently C1-C4 alkyl; C1-C4 haloalkyl; C2-C4 alkenyl; C1-C4 alkoxy; or phenyl;

each R26 is independently H; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, Cl-C4 alkyl, Cl-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; each R27 is independently C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C1 -C4 alkyl, C1-C4 haloalkyl, Cl-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; m, n and p are each independently 0, 1 or 2; risOor 1; and s is 2 or 3.

This invention also provides compounds of Formula II including all geometric and stereoisomers which are useful as intermediates for the preparation of the fungicides and arthropodicides of Formula I where Y is oxygen: wherein E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; A is O; S; N; NR5; or CR14; G is C or N; provided that when G is C, then A is O, S or NR5 and the floating double bond is attached to G; and when G is N, then A is N or CR14 and the floating double bond is attached to A; W is O; S; NH; N(C1-C6 alkyl); or NO(C1-C6 alkyl); Xis OR1; S(O)mR1; or halogen; R1 is C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; R2 is H; C1-C6 alkyl; Cl-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; hydroxy; C1-C2 alkoxy; or acetyloxy;

R3 and R4 are each independently halogen; cyano; nitro; hydroxy; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C2-C6 alkenyloxy; C2-C6 alkynyloxy; C1-C6 alkylthio; C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; formyl; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; NH2C(O); (C1-C4 alkyl)NHC(O); (C1-C4 alkyl)2NC(O); Si(R25)3; Ge(R25)3; (R25)3Si-C-C-; or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R8 and optionally substituted with one or more R 10; ol- when R3 and R4 are attached to adjacent atoms, R3 and R4 can be taken together as C3-C5 alkylene, C3-C5 haloalkylene, C3-C5 alkenylene or C3-C5 haloalkenylene each optionally substituted with 1-2 C1-C3 alkyl; R5 is H; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; R8 is H; 1-2 halogen; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C1-C6 alkylthio; C1-C6 haloalkylthio; C1-C6 alkylsulfinyl; Cl-C6 alkylsulfonyl; C3-C6 cycloalkyl; C3-C6 alkenyloxy; CO2(CI-C6 alkyl); NH(C1-C6 alkyl); N(C1-C6 alkyl)2; cyano; nitro; SiR19R20R21; or GeR19R20R21; each R10 is independently halogen; C1-C4 alkyl; Cl-C4 haloalkyl; Cl-C4 alkoxy; nitro; or cyano; R14 is H; halogen; C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; or C3-C6 cycloalkyl; R19, R20 and R21 are each independently C1-C6 alkyl; C2-C6 alkenyl; Cl-C4 alkoxy; or phenyl; each R25 is independently C1-C4 alkyl; C1-C4 haloalkyl; C2-C4 alkenyl; Cl-C4 alkoxy; or phenyl; and mis 1 or2.

DETAILS OF THE INVENTION In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 CH3" indicates that the substituent can be methyl or, when there is a hydrogen attached to the same atom, the substituent and said hydrogen can both be methyl.

"Alkenyl" includes straight-chain or branched alkenes such as vinyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also

includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkylene" denotes a straight-chain alkanediyl. Examples of "alkylene" include CH2CH2CH2, CH2CH2CH2CH2, CH2CH2CH2CH2CH2. "Alkenylene" denotes a straight-chain alkenediyl containing one olefinic bond. Examples of "alkenylene" include CH2CH=CH, CH2CH2CH=CH, CH2CH=CHCH2 and CH2CH=CHCH2CH2. "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxv and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. "Alkoxyalkoxy" denotes alkoxy substitution on alkoxy. "Alkenyloxy" includes straight-chain or branched alkenyloxy moieties. Examples of "alkenyloxy" include H2C=CHCH2O, (CH3)2C=CHCH2O, (CH3)CH=CHCH2O, (CH3)CH=C(CH3)CH2O and CH2=CHCH2CH2O. "Alkynyloxy" includes straight-chain or branched alkynyloxy moieties. Examples of "alkynyloxy" include HC-CCH2O, CH3C=-CCR2O and CH3C=-CCH2CH2O. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylthioalkyl" denotes alkylthio substitution on alkyl. Examples of "alkylthioalkyl" include CH3SCH, CH3SCH2CH2, CH3CH2SCH2 CH3CH2CH2CH2SCH2 and CH3cH2scH2cH2 "Alkylthioalkylthio" denotes alkylthio substitution on alkylthio. Analogously, "alkylthioalkoxy" denotes alkylthio substitution on alkoxy. "Alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH3S(O).

CH3CH2S(O), CH3CH2CH2S(O), (CH3)2CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(0)7.

CH3CH2S(°)2, CH3CH2CH2S(°)2, (CH3)2CHS(0)2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Alkenylthio" is defined analogously to the above examples. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. "Cycloalkenyl" includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1 ,4-cyclohexadienyl. "Trialkylsilylalkoxyalkoxy" denotes trialkylsilylalkoxy substitution on alkoxy. Examples of "trialkylsilylalkoxyalkoxy" includes, for example, (CH3)3SiCH2CH2OCH2O. The term "aromatic carbocyclic ring system" includes fully aromatic carbocycles and carbocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the Hückel rule is satisfied). The term

"nonaromatic carbocyclic ring system" denotes fully saturated carbocycles as well as partially or fully unsaturated carbocycles where the Hückel rule is not satisfied by any of the rings in the ring system. The term "aromatic heterocyclic ring system" includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the Hückel rule is satisfied). The term "nonaromatic heterocyclic ring system" denotes fully saturated heterocycles as well as partially or fully unsaturated heterocycles where the Hückel rule is not satisfied by any of the rings in the ring system. The heterocyclic ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides.

The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. The term "1-2 halogen" indicates that one or two of the available positions for that substituent may be halogen which are independently selected. 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 F3C, CICH2, CF3CH2 and CF3CCl2. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1)2C=CHCH2 and CF3CH2CH=CHCH2. Examples of "haloalkynyl" include HC-CCHCl, CF3C-C, CCl3C-C and FCH2C~CCH2. Examples of "haloalkoxy" include CF30, CCl3CH2O, HCF2CH2CH2O and CF3CH2O. Examples of "haloalkylthio" include CCl3S, CF3S, CCl3CH2S and ClCH2CH2CH2S. Examples of "haloalkylsulfinyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Examples of "haloalkylsulfonyl" include Cm3 8(0)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(0)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 10. For example, C1 -C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl. Examples of "alkylcarbonyl" include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of "alkoxycarbonyl" include CH30C(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the different butoxy- or pentoxycarbonyl isomers. In the above recitations, when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

When a group contains a substituent which can be hydrogen, for example R9 or R13, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.

One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises compounds selected from Formula I, N-oxides and agriculturally suitable salts thereof. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.

The salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. The salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonium, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a phenol.

Preferred methods for reasons of better activity and/or ease of synthesis are: Preferred 1. Methods for controlling arthropods using compounds of Formula I above, and N-oxides and agriculturally suitable salts thereof, wherein: E is selected from the group 1,2-phenylene; 1,5-, 1,6-, 1,7-, 1,8-, 2,6-.

2,7-, 1,2-, and 2,3-naphthalenediyl; lH-pyrrole-1,2-, 2,3- and 3,4-diyl; 2,3- and 3,4-furandiyl; 2,3- and 3,4-thiophenediyl; lH-pyrazole-1,5-, 3,4- and 4,5-diyl; lH-imidazole-1,2-, 4,5- and 1,5-diyl; 3,4- and 4,5-isoxazolediyl; 4,5-oxazolediyl; 3,4- and 4,5-isothiazolediyl; 4,5-thiazolediyl; 1 H- 1,2, 3-triazole- 1,5- and 4,5-diyl; 2H- 1 ,2,3-triazole-4,5-diyl; 1H- 1,2,4-triazole- 1 ,5-diyl; 4H- 1,2,4-triazole-3,4-diyl; 1,2,3-oxadiazole-4,5-diyl; 1,2,5-oxadiazole-3,4-diyl; 1,2,3-thiadiazole-4,5-diyl; 1,2, 5-thiadiazole- 3,4-diyl; 1H-tetrazole- 1 ,5-diyl; 2,3- and 3,4-pyridinediyl; 3,4- and 4,5-pyridazinediyl; 4,5-pyrimidinediyl; 2,3-pyrazinediyl; 1,2,3-triazine-4,5-diyl; 1,2,4-triazine-5, 6-diyl; 1H-indole-1,4-, 1,5-, 1,6-, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-,

3,6-, 3,7-, 1,2-, 2,3-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl; benzo[b]thiophene-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-, 4,5-, 5,6- and 6,7-diyl; lH-indazole-1,4-, 1,5-, 1,6-, 1,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; lH-benzimidazole-l,4-, 1,5-, 1,6-, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-diyl; 1,2-benzisoxazole-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-benzoxazolediyl; 1,2-benzisothiazole-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-benzothiazolediyl; 2,5-, 2,6-, 2,7-, 2,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 2,3-, 3,4-, 5,6-, 6,7- and 7,8-quinolinediyl; 1,5-, 1,6-, 1,7-, 1,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 3,4-, 5,6-, 6,7- and 7,8-isoquinolinediyl; 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 3,4-, 5,6-, 6,7- and 7,8-cinnolinediyl; 1,5-, 1,6-, 1,7-, 1,8-, 5,6-, 6,7- and 7,8-phthalazinediyl; 2,5-, 2,6-, 2,7-, 2,8-, 4,5-, 4,6-, 4,7-, 4,8-, 5,6-, 6,7- and 7,8-quinazolinediyl; 2,5-, 2,6-, 2,7-, 2,8-, 2,3-, 5,6-, 6,7- and 7,8-quinoxalinediyl; 1,8,-naphthyridine-2,5-, 2,6-, 2,7-, 3,5-, 3,6-, 4,5-, 2,3- and 3,4-diyl; 2,6-, 2,7-, 4,6-, 4,7-, 6,7-pteridinediyl; pyrazolo[5,1-b]thiazole-2,6-, 2,7-, 3,6-, 3,7-, 2,3- and 6,7-diyl; thiazolo[2,3-c]-1,2,4-triazole-2,5-, 2,6-, 5,6-diyl; 2-oxo- 1 ,3-benzodioxole-4,5- and 5 ,6-diyl; 1,3-dioxo- 1H-isoindole-2,4-, 2,5-, 4,5- and 5 ,6-diyl; 2-oxo-2H-1-benzopyran-3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 5,6-, 6,7- and 7,8-diyl; [1,2,4]triazolo[1,5-a]pyridine-2,5-, 2,6-, 2,7-, 2,8-, 5,6-, 6,7- and 7,8-diyl; 3,4-dihydro-2,4-dioxo-2H- 1,3-benzoxazine-3 ,5-, 3,6-, 3,7-, 3,8-, 5,6-, 6,7- and 7,8-diyl; 2,3-dihydro-2-oxo-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-benzofurandiyl; thieno[3,2-dlthiazole-2,5-, 2,6-, and 5,6-diyl; 5,6,7,8-tetrahydro-2,5-, 2,6-, 2,7-, 2,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 2,3- and 3,4-quinolinediyl; 2,3-dihydro- 1,1 3-trioxo- 1 ,2-benzisothiazole-2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-diyl; 1,3-benzodioxole-2,4-, 2,5-, 4,5- and 5,6-diyl; 2,3-dihydro-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-benzofurandiyl; 2,3-dihydro- 1 ,4-benzodioxin-2,5-, 2,6-, 2,7-, 2,8-, 5,6- and 6,7-diyl;

and 5 ,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2,4-, 2,5-, 2,6-, 2,7-, 2,8-, 3,4-, 3,5-, 3,6-, 3,7-, 3,8-, and 2,3-diyl; each aromatic ring system optionally substituted with one of R3, R4, or both R3 and R4; W is O; R1 is C1-C3 alkyl or C1-C3 haloalkyl; R2 is H; C1-C6 alkyl; C1-C6 haloalkyl; or C3-C6 cycloalkyl; R3 and R4 are each independently halogen; cyano; nitro; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C1-C6 alkylthio; C1-C6 alkylsulfonyl; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; (Cl-C4 alkyl)NHC(O); (C1-C4 alkyl)2NC(O); benzoyl; or phenylsulfonyl; Y is -0-; -S(O)n-; -NR15-; -C(=O)-; -CH(OR15)-; -CH2-, -CH2CH2-; -CH=CH-; -CrC-; -CH20-; -OCH2-; -CH?S(O),-; -S(O),CH-, -CH20-N=C(R7)-; -(R7)C=N-OCH(R'S)-; -C(R7)=N-O-; or a direct bond; R7 is H; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 alkylthio; C2-C6 alkenyl; C2-C6 alkynyl; C3-C6 cycloalkyl; halogen; or cyano; or when Y and an R10 are attached to adjacent atoms on Z and Y is -CH2O-N=C(R7)-, R7 and said adjacently attached R10 can be taken together as -(CH2)r-J- such that J is attached to Z; Z is selected from the group Cl-Cl0 alkyl; C3-C8 cycloalkyl; phenyl; naphthalenyl; anthracenyl; phenanthrenyl; 1H-pyrrolyl; furanyl; thienyl; lH-pyrazolyl; lH-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl; thiazolyl; 1H-1,2,3-triazolyl; 2H-1,2,3-triazolyl; lH- 1 2,4-triazolyl; 4H- 1 2,4-triazolyl; 1 2,3-oxadiazolyl; 1,2,4-oxadiazolyl; 1,2,5-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,3-thiadiazolyl; 1,2,4-thiadiazolyl; 1,2,5-thiadiazolyl; 1,3,4-thiadiazolyl; 1H-tetrazolyl; 2H-tetrazolyl; pyridinyl; pyridazinyl; pyrimidinyl; pyrazinyl; 1,3,5-triazinyl; 1,2,4-triazinyl; 1,2,4,5-tetrazinyl; 1H-indolyl; benzofuranyl; benzo[b]thiophenyl; 1H-indazolyl; 1 H-benzimidazolyl; benzoxazolyl; benzothiazolyl; quinolinyl; isoquinolinyl; cinnolinyl; phthalazinyl; quinazolinyl; quinoxalinyl; 1,8-naphthyridinyl; pteridinyl; 2,3-dihydro-1H-indenyl; 1,2,3 ,4-tetrahydronaphthalenyl;

6,7,8 ,9-tetrahydro-5H-benzocycloheptenyl; <BR> <BR> <BR> <BR> <BR> <BR> 5 ,6,7 ,8 ,9,1 O-hexahydrobenzocyclooctenyl; 2, 3-dihydro- 3-oxobenzofuranyl; 1, 3-dihydro- 1 -oxoisobenzofurany l; 2,3-dihydro-2-oxobenzofuranyl; 3 ,4-dihydro-4-oxo-2H- 1 -benzopyranyl; 3,4-dihydro-1-oxo-1H-2-benzopyranyl; 3,4-dihydro-3-oxo- lH-2-benzopyranyl; 3,4-dihydro-2-oxo-2H- 1 -benzopyranyl; 4-oxo-4H- 1 -benzopyranyl; 2-oxo-2H- 1 -benzopyranyl; 2,3,4,5-tetrahydro-5-oxo-1-benzoxepinyl; 2,3,4,5-tetrahydro-2-oxo- 1 -benzoxepinyl; 2,3-dihydro- 1,3 -dioxo- tH-isoindolyl; 1,2,3,4-tetrahydro-1,3-dioxoisoquinolinyl; <BR> <BR> <BR> 3 ,4-dihydro-2,4-dioxo-2H- 1,3 -benzoxazinyl; <BR> <BR> <BR> <BR> <BR> <BR> 2-oxo- 1 ,3-benzodioxyl; <BR> <BR> <BR> <BR> <BR> <BR> 2,3-dihydro- 1,1 3-trioxo- 1 ,2-benzisothiazolyl; 9H-fluorenyl; azulenyl; and thiazolo[2,3-c]-1,2,4-triazolyl; each group substituted with R9 and optionally substituted with one or more R10; and R15 is H; C1-C3 alkyl; or C3-C6 cycloalkyl.

Preferred 2. Methods of Preferred 1 wherein: E is selected from the group 1,2-phenylene; 1,6-, 1,7-, 1,2-, and 2,3-naphthalenediyl; 2,3- and 3,4-furandiyl; 2,3- and 3 ,4-thiophenediyl; 2,3- and 3 ,4-pyridinediyl; 4,5-pyrimidinediyl; 2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl; and benzo[b]thiophene-2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-diyl; each aromatic ring system optionally substituted with one of R3, R4, or both R3 and R4; Z is selected from the group phenyl; naphthalenyl; 2-thiazolyl; 1,2,4-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,4-thiadiazolyl; 1,3,4-thiadiazolyl; pyridinyl; and pyrimidinyl; each group substituted with R9 and optionally substituted with one or more R10; R7 is H; Cl-C6 alkyl; C1-C6 haloalkyl; Cl-C6 alkoxy; C1-C6 alkylthio; C2-C6 alkenyl; C2-C6 alkynyl; cyclopropyl; halogen; or cyano; or when Y and an R10 are attached to adjacent atoms on Z and Y is -CH2O-N=C(R7)-, R7 and said adjacently attached R10 can be taken together as -(CH2)r-J- such that J is attached to Z;

J is -CH2- or -CH2CH2-; and ris 1.

Preferred 3. Methods of Preferred 2 wherein: E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; AisOorN; Xis OR1; R1 is C1-C3 alkyl; R2 is H or C1-C2 alkyl; Y is -O-; -S(O)n-; -NR15-; -C(=O)-; -CH(OR15)-; -CH2-; -CH2CH2-; -CH=CH-; -C#C-; -CH2O-; -OCH2-; -CH2s(o)n-; -S(O)nCR2-; or a direct bond; Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,4-thiadiazolyl; and 1,3,4-thiadiazolyl; each group substituted with R9 and optionally substituted with R10; and R15 is H; C1-C3 alkyl; or cyclopropyl.

Preferred 4. Methods of Preferred 3 wherein: R1 is methyl; R2 is methyl; Y is -O-; -S(O)n-; -NR15-; -C(=O)-; -CH(OR15)-; -CH2-; or a direct bond; and R9 is H; halogen; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C1-C6 alkylthio; C1-C6 haloalkylthio; C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; C3-C6 cycloalkyl; CO2(C1-C6 alkyl); -C(R18)-NOR17; cyano; nitro; SF5; SiR22R23R24; or GeR22R23R24; or R9 is phenyl, benzyl, phenoxy, pyridinyl, thienyl, furanyl, or pyrimidinyl each optionally substituted with one of R11, R12, or both R11 and R12.

Preferred 5. Methods of Preferred 4 wherein: Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; and 1,2,4-thiadiazolyl; each group substituted with R9 and optionally substituted with R10; and Y is -O-; and R9 is phenyl optionally substituted with one of R11, R12, or both R1 i and R12.

Most preferred are methods of Preferred 5 where the compound is selected from the group: 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5 -yl]oxy]phenyl]-2,4- dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one; and 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5 -yl]oxy]-6- methylphenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazo l-3-one.

Preferred compounds of Formula IA for reasons of better arthropodicidal or fungicidal activity and/or ease of synthesis are: Preferred 1A. Compounds of Formula IA above, and N-oxides and agriculturally suitable salts thereof, wherein: R1 is methyl; R2 is methyl; Y is -O-; -S(O)n-; -NR15-; -C(=O)-; -CH(OR15)-; -CH2-; or a direct bond; and R9 is H; halogen; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C1-C6 alkylthio; C1-C6 haloalkylthio; C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; C3-C6 cycloalkyl; CO2(C1-C6 alkyl); -C(R18)=NoRl7; cyano; nitro; SF5; SiR22R23R24; or GeR22R23R24; or R9 is phenyl, benzyl, phenoxy, pyridinyl, thienyl, furanyl, or pyrimidinyl each optionally substituted with one of R11, R12, or both R11 and R12.

Preferred 2A. Compounds of Preferred 1A wherein: Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; 1,2,4-thiadiazolyl; and pyrazinyl; each group substituted with R9 and optionally substituted with R10; and Y is -O-; and R9 is phenyl optionally substituted with one of R1 1, R12, or both R1 9 and R12.

Most preferred are compounds of Preferred 1A selected from the group: 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5 -yl]oxy]phenyl]-2,4- dihydro-5-methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one; 4-[2-[[3-[3 ,5-bis(trifluoromethyl)phenyl]- 1 ,2,4-thiadiazol-5-yl]oxy]-6- methylphenyl]-2,4-dihydro-5-methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one; 4-[2-[[3-(1,1-dimethylethyl)-1,2,4-thiadiazol-5-yl]oxy]-6-me thylphenyl]-2,4- dihydro-5-methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one;

4-[2-[[3-( 1,1 -dimethylethyl)- 1 ,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4-dihydro-5- methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one; 4-[2-[[3-(3,4-dichlorophenyl)- 1 ,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4-dihydro-5- methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one; 2,4-dihydro-5-methoxy-2-methyl-4- [2- [[3- [3-(trifluoromethoxy)phenylj - 1,2,4- thiadiazol-5-yl]oxy]phenyl]-3H 1 ,2,4-triazol-3-one; 4-[2-[[3-(4-bromophenyl)- 1 ,2,4-thiadiazol-5-yl]oxyjphenyl] -2,4-dihydro-5- methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one; 2,4-dihydro-5-methoxy-2-methyl-4- [2- [ [5-methyl-4- [3-(trifluoromethyl)phenylj - 2-thiazolyl]oxylphenyl]-3H- 1 ,2,4-triazol-3-one; and 2,4-dihydro-5-methoxy-2-methyl-4- [2- [ [6- [4-(trifluoromethyl)phenyl] -2- pyrazinyl]oxy]phenyl]-3H- 1 ,2,4-triazol-3-one.

This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of Formula IA and at least one of a surfactant, a solid diluent or a liquid diluent. The preferred compositions of the present invention are those which comprise the above preferred compounds of Formula IA.

This invention also relates to a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of the compounds of Formula IA and the compositions described herein. The preferred methods of use are those involving the above preferred compounds of Formula IA.

This invention also relates to arthropodicidal compositions comprising arthropodicidally effective amounts of the compounds of Formula IA and at least one of a surfactant, a solid diluent or a liquid diluent. The preferred compositions of the present invention are those which comprise the above preferred compounds of Formula IA.

This invention also relates to a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of the compounds of Formula IA and the compositions described herein. The preferred methods of use are those involving the above preferred compounds of Formula IA.

Preferred compounds of Formula IB for reasons of better fungicidal or arthropodicidal activity and/or ease of synthesis are: Preferred 1B. Compounds of Formula IB above, and N-oxides and agriculturally suitable salts thereof, wherein: E is selected from the group 1,2-phenylene; 1,5-, 1,6-, 1,7-, 1,8-, 2,6-, 2,7-, 1,2-, and 2,3-naphthalenediyl; 1H-pyrrole-1,2-, 2,3- and

3,4-diyl; 2,3- and 3,4-furandiyl; 2,3- and 3,4-thiophenediyl; lH-pyrazole-1,5-, 3,4- and 4,5-diyl; lH-imidazole-1,2-, 4,5- and 1,5-diyl; 3,4- and 4,5-isoxazolediyl; 4,5-oxazolediyl; 3,4- and 4,5-isothiazolediyl; 4,5-thiazolediyl; 1H- 1 ,2,3-triazole- 1,5- and 4,5-diyl; 2H-1,2,3-triazole-4,5-diyl; 1H-1,2,4-triazole-1,5-diyl; 4H-1,2,4-triazole-3,4-diyl; 1,2,3-oxadiazole-4,5-diyl; 1,2,5-oxadiazole-3 ,4-diyl; 1 ,2,3-thiadiazole-4,5-diyl; 1 ,2,5-thiadiazole-3,4-diyl; 1H-tetrazole- 1 ,5-diyl; 2,3- and 3 ,4-pyridinediyl; 3,4- and 4,5-pyridazinediyl; 4,5-pyrimidinediyl; 2,3-pyrazinediyl; 1 ,2,3-triazine-4,5-diyl; 1,2,4-triazine-5 ,6-diyl; 1H-indole-1,4-, 1,5-, 1,6-, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 1,2-, 2,3-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl; benzo[b]thiophene-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-.

4,5-, 5,6- and 6,7-diyl; lH-indazole-1,4-, 1,5-, 1,6-, 1,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; lH-benzimidazole-1,4-, 1,5-, 1,6-.

1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-diyl; 1,2-benzisoxazole-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-benzoxazolediyl; 1,2-benzisothiazole-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-benzothiazolediyl; 2,5-, 2,6-, 2,7-, 2,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 2,3-, 3,4-, 5,6-,6,7-and7,8-quinolinediyl; 1,5-, 1,6-, 1,7-, 1,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 3,4-, 5,6-, 6,7- and 7,8-isoquinolinediyl; 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 3,4-, 5,6-,6,7-and7,8-cinnolinediyl;l,5-, 1,6-, 1,7-, 1,8-, 5,6-, 6,7- and 7,8-phthalazinediyl; 2,5-, 2,6-, 2,7-, 2,8-, 4,5-, 4,6-, 4,7-, 4,8-, 5,6-, 6,7- and 7,8-quinazolinediyl; 2,5-, 2,6-, 2,7-, 2,8-, 2,3-, 5,6-, 6,7- and 7,8-quinoxalinediyl; 1,8,-naphthyridine-2,5-, 2,6-, 2,7-, 3,5-, 3,6-, 4,5-, 2,3- and 3,4-diyl; 2,6-, 2,7-, 4,6-, 4,7-, 6,7-pteridinediyl: pyrazolo[5,1-b]thiazole-2,6-, 2,7-, 3,6-, 3,7-, 2,3- and 6,7-diyl; thiazolo[2,3-cj- 1 ,2,4-triazole-2,5-, 2,6-, 5 ,6-diyl; 2-oxo-1,3-benzodioxole-4,5- and 5,6-diyl; 1,3-dioxo-1H-isoindole-2,4-, 2,5-, 4,5- and 5 ,6-diyl; 2-oxo-2H-1-benzopyran-3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 5,6-, 6,7- and 7,8-diyl; [1,2,4]triazolo[l ,5-a]pyridine-2,5-, 2,6-,

2,7-, 2,8-, 5,6-, 6,7- and 7,8-diyl; 3,4-dihydro-2,4-dioxo-2H- 1,3-benzoxazine-3 ,5-, 3,6-, 3,7-, 3,8-, 5,6-, 6,7- and 7,8-diyl; 2,3-dihydro-2-oxo-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-benzofurandiyl; thieno[3,2-d]thiazole-2,5-, 2,6-, and 5,6-diyl; 5,6,7,8-tetrahydro-2,5-, 2,6-, 2,7-, 2,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 2,3- and 3,4-quinolinediyl; 2,3-dihydro- 1,1 ,3-trioxo- 1 ,2-benzisothiazole-2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-diyl; 1,3-benzodioxole-2,4-, 2,5-, 4,5- and 5,6-diyl; 2,3-dihydro-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-benzofurandiyl; 2,3-dihydro-l,4-benzodioxin-2,5-, 2,6-, 2,7-, 2,8-, 5,6- and 6,7-diyl; and 5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2,4 , 2,5 , 2,6 .

2,7-, 2,8-, 3,4-, 3,5-, 3,6-, 3,7-, 3,8-, and 2,3-diyl; each aromatic ring system optionally substituted with one of R3, R4, or both R3 and R4; W is O; R1 is C1-C3 alkyl or C1-C3 haloalkyl; R2 is H; C1-C6 alkyl; C1-C6 haloalkyl; or C3-C6 cycloalkyl; R3 and R4 are each independently halogen; cyano; nitro; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C1-C6 alkylthio; C1-C6 alkylsulfonyl; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; (C1-C4 alkyl)NHC(O); (C1 -C4 alkyl)2NC(O); benzoyl; or phenylsulfonyl; Y is -O-; -S(O) n-; -NR15-; -C(=O)-; -CH(OR 15)-; -CH2-; -CH2CH2-; -CH=CH-; -C-C-; -CH2O-; -OCH2-; -CR2S(O)n-; -S(O)nCR2-; -CH2O-N=C(R7)-; -(R7)C=N-OCH(R15)-; -C(R7)=N-O-; or a direct bond; R7 is H; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 alkylthio; C2-C6 alkenyl; C2-C6 alkynyl; C3-C6 cycloalkyl; halogen; or cyano; or when Y and an R10 are attached to adjacent atoms on Z and Y is -CH2O-N=C(R7)-, R7 and said adjacently attached R10 can be taken together as -(CH2)r-J- such that J is attached to Z; Z is selected from the group C1-C10 alkyl; C3-C8 cycloalkyl; phenyl; naphthalenyl; anthracenyl; phenanthrenyl; lH-pyrrolyl; furanyl; thienyl; 1H-pyrazolyl; 1H-imidazolyl; isoxazolyl; oxazolyl;

isothiazolyl; thiazolyl; lH-1,2,3-triazolyl; 2H-1,2,3-triazolyl; 1H-1,2,4-triazolyl; 4H-1,2,4-triazolyl; 1,2,3-oxadiazolyl; 1,2,4-oxadiazolyl; 1,2,5-oxadiazolyl; 1,3 ,4-oxadiazolyl; 1,2,3-thiadiazolyl; 1,2,4-thiadiazolyl; 1,2,5-thiadiazolyl; 1,3 ,4-thiadiazolyl; 1 H-tetrazolyl; 2H-tetrazolyl; pyridinyl; pyridazinyl; pyrimidinyl; pyrazinyl; 1,3,5-triazinyl; 1,2,4-triazinyl; 1,2,4,5-tetrazinyl; 1H-indolyl; benzofuranyl; benzo[b]thiophenyl; 1H-indazolyl; 1H-benzimidazolyl; benzoxazolyl; benzothiazolyl; quinolinyl; isoquinolinyl; cinnolinyl; phthalazinyl; quinazolinyl; quinoxalinyl; 1,8-naphthyridinyl; pteridinyl; 2,3-dihydro-1H-indenyl; 1 ,2,3,4-tetrahydronaphthalenyl; 6,7,8 ,9-tetrahydro- 5H-benzocycloheptenyl; 5,6,7,8,9,10-hexahydrobenzocyclooctenyl; 2,3-dihydro-3-oxobenzofuranyl; 1 ,3-dihydro- 1 -oxoisobenzofuranyl; 2,3-dihydro-2-oxobenzofuranyl; 3,4-dihydro-4-oxo-2H-1-benzopyranyl; 3,4-dihydro-1-oxo-1H-2-benzopyranyl; 3,4-dihydro-3-oxo-1H-2-benzopyranyl; 3 ,4-dihydro-2-oxo-2H- 1 -benzopyranyl; 4-oxo-4H- 1 -benzopyranyl; 2-oxo-2H- 1 -benzopyranyl; 2,3,4,5-tetrahydro-5-oxo- 1 -benzoxepinyl; 2,3 ,4,5-tetrahydro-2-oxo- 1 -benzoxepinyl; 2,3-dihydro-1,3-dioxo-1H-isoindolyl; 1,2,3 ,4-tetrahydro- 1 3-dioxoisoquinolinyl; <BR> <BR> <BR> 3 ,4-dihydro-2,4-dioxo-2H- 1 ,3-benzoxazinyl; <BR> <BR> <BR> <BR> <BR> 2-oxo- 1 ,3-benzodioxyl; 2,3-dihydro- 1,1 ,3-trioxo- 1 ,2-benzisothiazolyl; 9H-fluorenyl; azulenyl; and thiazolo[2,3-c]-1,2,4-triazolyl; each group substituted with R9 and optionally substituted with one or more R 10; and R15 is H; C1-C3 alkyl; or C3-C6 cycloalkyl.

Preferred 2B. Compounds of Preferred 1B wherein: E is selected from the group 1,2-phenylene; 1,6-, 1,7-, 1,2-, and 2,3-naphthalenediyl; 2,3- and 3,4-furandiyl; 2,3- and 3 ,4-thiophenediyl; 2,3- and 3 ,4-pyridinediyl; 4,5-pyrimidinediyl; 2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl; and benzo[b]thiophene-2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-diyl;

each aromatic ring system optionally substituted with one of R3, R4, or both R3 and R4; Z is selected from the group phenyl; naphthalenyl; 2-thiazolyl; 1,2,4-oxadiazolyl; 1,3 ,4-oxadiazolyl; 1,2,4-thiadiazolyl; 1,3,4-thiadiazolyl; pyridinyl; and pyrimidinyl; each group substituted with R9 and optionally substituted with one or more R10; R7 is H; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 alkylthio; C2-C6 alkenyl; C2-C6 alkynyl; cyclopropyl; halogen; or cyano; or when Y and an R10 are attached to adjacent atoms on Z and Y is -CH2O-N=C(R7)-, R7 and said adjacently attached R10 can be taken together as -(CH2)r-J- such that J is attached to Z; J is -CH2- or -CH2CH2-; and ris 1.

Preferred 3B. Compounds of Preferred 2B wherein: E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; A is O or N; Xis OR1; R1 is C1-C3 alkyl; R2 is H or C1-C2 alkyl; Y is -O-; -S(O) n-; -NR15-; -C(=O)-; -CH(OR15)-; -CH2-; -CH2CH2-; -CH=CH-; -C-C-; -CH2O-; -OCH2-; -CH2S(O)n-; -S(O)nCR2-; or a direct bond; Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; 1,3 ,4-oxadiazolyl; 1 ,2,4-thiadiazolyl; and 1,3,4-thiadiazolyl; each group substituted with R9 and optionally substituted with R10; and R15 is H; C1-C3 alkyl; or cyclopropyl.

Preferred 4B. Compounds of Preferred 3B wherein: R1 is methyl; R2 is methyl; Y is -O-; -S(O),-; -NR15-; -C(=O)-; -CH(oR15)-; -CH2-; or a direct bond; and R9 is phenyl, benzyl, phenoxy, pyridinyl, thienyl, furanyl, or pyrimidinyl each substituted with R11 and optionally substituted with R12.

Preferred SB. Compounds of Preferred 4B wherein: Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; and 1,2,4-thiadiazolyl; each group substituted with R9 and optionally substituted with R10; and Y is -O-; and R9 is phenyl substituted with R11 and optionally substituted with R12.

Most preferred are compounds of Preferred 5B selected from the group: 4-[2-[[3-(3-ethynylphenyl)- 1 ,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4-dihydro-5- methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one; and [3-[5-[2-(1 ,5-dihydro-3-methoxy- 1 -methyl-5-oxo-4H- 1 ,2,4-triazol-4- yl)phenoxyj- 1 ,2,4-thiadiazol-3-yljphenylj trifluoromethanesulfonate.

This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of Formula IB and at least one of a surfactant, a solid diluent or a liquid diluent. The preferred compositions of the present invention are those which comprise the above preferred compounds of Formula IB.

This invention also relates to a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of the compounds of Formula IB and the compositions described herein. The preferred methods of use are those involving the above preferred compounds of Formula IB.

This invention also relates to arthropodicidal compositions comprising arthropodicidally effective amounts of the compounds of Formula IB and at least one of a surfactant, a solid diluent or a liquid diluent. The preferred compositions of the present invention are those which comprise the above preferred compounds of Formula IB.

This invention also relates to a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of the compounds of Formula IB and the compositions described herein. The preferred methods of use are those involving the above preferred compounds of Formula IB.

Preferred intermediates for the preparation of the fungicides and arthropodicides of Formula I where Y is oxygen are: Preferred 1C. Compounds of Formula II above wherein: W is O; R1 is C1-C3 alkyl or C1-C3 haloalkyl; R2 is H; C1-C6 alkyl; C1-C6 haloalkyl; or C3-C6 cycloalkyl; and

R3 and R4 are each independently halogen; cyano; nitro; C1 -C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy; C1-C6 haloalkoxy; C 1-C6 alkylthio; Cl-C6 alkylsulfonyl; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; (C1-C4 alkyl)NHC(O); (C1-C4 alkyl)2NC(O); benzoyl; or phenylsulfonyl.

Preferred 2C. Compounds of Preferred 1C wherein A is O or N; X is OR or halogen; R is C1-C3 alkyl; R2 is H or C1-C2 alkyl; and R3 and R4 are each independently halogen; C1-C3 alkyl; C1-C3 alkoxy; or C1-C3 alkylthio.

Preferred 3C.. Compounds of Preferred 2C wherein: A is N; R1 is methyl; R2 is methyl; and R3 and R4 are each independently halogen or methyl.

Most preferred are compounds of Preferred 3C selected from the group: 2,4-arihydro-4-(2-hydroxyphenyl)-5-methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one; 2A-dihydroA -(2-hydroxy-6-methylphenyl)-5 -methoxy-2 -methyl-3H- 1 ,2,4 - triazol-3 -one; 5-chloro-2,4-dihydro-4-(2-hydroxy-6-methylphenyl)-2-methyl-3 H-1,2,4-triazol- 3-one; and

5-chloro-2,4-aihydro4-(2-hydroxyphenyl)-2-methyl-3H- 1 ,2,4-triazol -3 -one .

Of note are embodiments where X is other than H; embodiments where R2 is H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;

embodiments where Y is -O-, -S(O)n-, -NR15-, -C(=O)-, -CH(OR15)-, -CHR6-, -CHR6CHR6-, -CR6=CR6-, -C#C-, -CHR15O-, -OCHR15-, -CRR15S(O)n-, -S(O)nCHR15-, -CHR15O-N=C(R7)-, -(R7)C=N-OCH(R15)-, -C(R7)=N-O-, -O-N=C(R7)-, -CHR15OC(=O)N(R15)-, -CHR15OC(=S)N(R15)-, -CHR15O-N(R15)C(=O)N(R15)-, -CHR15O-N(R15)C(=S)N(R15)-, -CHR1 50-N-C(R7)NR15 -, -CHR15O-N=C(R7)OCH2-, -CHR 50-N-C(R7 )-N=N-, -CHR15O-N=C(R7)-C(=O)-, -CHR15S-C(R7)=N-, -C(R7)=N-NR15-, -CH=N-N=C(R7)-, -CHR15N(COCH3)-N=C(R7)-, -OC(=S)NR15C(=O)-, -CHR6-C(=W )-A -, -CHR6CHR6-C(=W )-A -, -CR6=CR6-C(=W )-A -,

-C=-C-C(=W1)-A1-, -N=CR6-C(=W1)-A1- or a direct bond; embodiments where R7 is H, C1-C6 alkyl, C1-C6 haloalkyl, Cl-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, Cl-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, halogen, cyano or morpholinyl; embodiments where Z is other than C3-C8 cycloalkenyl and adamantyl each substituted with R9 and optionally substituted with one or more R10; embodiments where, when Y and an R10 are attached to adjacent atoms on Z and Y is -CHR15O-N=C(R7)-, -O-N=C(R7)-, -CH=N-N=C(R7)- or -CHR15N(CoCH3)-N=C(R7)-, R7 and said adjacently attached R10 are taken together as -(CR2)r-J- such that J is attached to Z; embodiments where R11 and R12 are each independently halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, Cl-C4 alkylthio, Cl-C4 haloalkylthio, Cl-C4 alkylsulfinyl, Cl-C4 haloalkylsulfinyl, C1 -C4 alkylsulfonyl, Cl-C4 haloalkylsulfonyl, C3-C6 alkenylthio, C3-C6 haloalkenylthio, nitro, cyano, SF5, Si(R25)3 or Ge(R25)3; embodiments where R19, R20, R21, R22, R23, and R24 are each independently C1-C6 alkyl, Cl-C4 alkoxy or phenyl; embodiments where each R25 is independently C1-C4 alkyl or phenyl; embodiments where R3 and R4 are each independently halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, Cl-C6 alkoxy, C1-C6 haloalkoxy, Cl-C6 alkylsulfonyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, (Cl-C4 alkyl)NHC(O), (Cl-C4 alkyl)2NC(O), benzoyl or phenylsulfonyl; embodiments where Z is selected from the group 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl and 1,3,4-thiadiazolyl, each group substituted with R9; embodiments where R11 is C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C3-C6 alkenylthio, C3-C6 haloalkenylthio or SF5; embodiments where R12 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C3-C6 alkenylthio, C3-C6 haloalkenylthio, nitro, cyano, SF5, Si(R25)3 or Ge(R25)3; embodiments where Z is selected from the group phenyl, naphthalenyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, pyridinyl and pyrimidinyl, each group substituted with R9 and optionally substituted with one or more R10; and embodiments where Z is

selected from the group 1 ,2,4-oxadiazolyl and 1,2,4-thiadiazolyl, each group substituted with R9.

The compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-33. One skilled in the art will recognize that compounds of Formula IA and IB are encompassed by Formula I and, therefore, can be prepared by these procedures. The definitions of E, A, G, W, X, R1-R27, Y, 21, W1, A1-A3, Z, Q, J, m, n, p, rand sin the compounds of Formulae 1-58 below are as defined above in the Summary of the Invention. Compounds of Formulae Ia-Im are various subsets of the compounds of Formula I, and all substituents for Formulae Ia-Im are as defined above for Formula I.

One skilled in the art will recognize that some compounds of Formula I can exist in one or more tautomeric forms. For example, a compound of Formula I wherein R2 is H may exist as tautomer Ia or Ib, or both Ia and Th. The present invention comprises all tautomeric forms of compounds of Formula I.

The compounds of Formula I can be prepared as described below in Procedures 1) to 5). Procedures 1) to 4) describe syntheses involving construction of the amide ring after the formation of the aryl moiety (E-Y-Z). Procedure 5) describes syntheses of the aryl moiety (E-Y-Z) with the amide ring already in place.

1) Alkvlation Procedures The compounds of Formula I are prepared by treating compounds of Formula 1 with an appropriate alkyl transfer reagent in an inert solvent with or without additional acidic or basic reagents or other reagents (Scheme 1). Suitable solvents are selected from the group consisting of polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide; ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.

Scheme 1 Y E Z E Z G W Methods 0 W 14 14 xy;y I R2 1 I I X = OH, SH, NH2, NH(C1-C6 alkyl) or NH(C1-C6 alko) X = OR1, SR1, NHRI, <BR> <BR> <BR> N(C-C6 alkyl)RI, or N(C1-C6 alkoxy)R Method 1: U-CH=N2 (U = H or (CH3)3Si) 2 NH Method 2: 03){ORl : ; Lewis acid C13 OR 3 Method 3: (R1)30+ BF4- 4 Method 4: (R1)2SO4; R1OSO2V; or R1-hal; optional base (hal = F, Cl, Br, or I) (V = C1-C6 alkyl, C1-C6 haloalkyl, or 4-CH3-C6H4) For example, compounds of Formula I can be prepared by the action of diazoalkane reagents of Formula 2 such as diazomethane (U = H) or trimethylsilyldiazomethane (U = (CH3)3Si) on dicarbonyl compounds of Formula 1 (Method 1). Use of trimethylsilyldiazomethane requires a protic cosolvent such as methanol. For examples of these procedures, see Chem. Pharm. Bull., (1984), 32, 3759.

As indicated in Method 2, compounds of Formula I can also be prepared by contacting carbonyl compounds of Formula 1 with alkyl trichloroacetimidates of Formula 3 and a Lewis acid catalyst. Suitable Lewis acids include trimethylsilyl triflate and tetrafluoroboric acid. The alkyl trichloroacetimidates can be prepared from the appropriate alcohol and trichloroacetonitrile as described in the literature (J. Danklmaier and H. Hiing, Synth. Commun., (1990), 20, 203).

Compounds of Formula I can also be prepared from compounds of Formula 1 by treatment with a trialkyloxonium tetrafluoroborate (i.e., Meerwein's salt) of Formula 4 (Method 3). The use of trialkyloxonium salts as powerful alkylating agents is well known in the art (see U. Schöllkopf, U. Groth, C. Deng, Angew. Chem., Int. Ed. Engl., (1981), 20, 798).

Other alkylating agents which can convert carbonyl compounds of Formula 1 to compounds of Formula I are dialkyl sulfates such as dimethyl sulfate, haloalkyl sulfonates such as methyl trifluoromethanesulfonate, and alkyl halides such as iodomethane and propargyl bromide (Method 4). These alkylations can be conducted with or without additional base. Appropriate bases include alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, or tertiary amines such as triethylamine, pyridine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine. See R. E. Benson, T. L. Cairns, J. Am. Chem. Soc., (1948), 70, 2115 for alkylation examples using agents of this type.

Compounds of Formula la (compounds of Formula 1 wherein G = C, W = 0 and X = OH) can be prepared by condensation of malonates or malonate derivatives of Formula 5 with an ambident nucleophile of Formula 6 (Scheme 2). The nucleophiles of Formula 6 are N-substituted hydroxylamines (HO-NHR2) and substituted hydrazines (HN(R5)-NHR2). Examples of such nucleophiles are N-methylhydroxylamine and methylhydrazine. The malonate esters of Formula 5 can be prepared by methods described hereinafter. The esters of Formula 5 can also be activated by first hydrolyzing the ester to form the corresponding carboxylic acid, and then converting the acid into the acid chloride (T = Cl) using thionyl chloride or oxalyl chloride, or into the acyl imidazole (T = 1-imidazolyl) by treating with 1,1 '-carbonyldiimidazole.

Scheme 2 T = O(C1-C4 alkyl), Cl, l-irrudazolyl Esters of Formula 5a can be prepared from copper (I)-catalyzed reaction of malonate esters of Formula 7 with substituted aryl halides of Formula 8 according to methods adapted from A. Osuka, T. Kobayashi and H. Suzuki, Synthesis, (1983), 67 and M. S. Malamas, T. C. Hohman, and J. Millen, J. Med. Chem., 1994, 37, 2043-2058, and illustrated in Scheme 3. Procedures to prepare compounds of Formula 8 are described below (see Scheme 32).

Malonate esters of Formula 5a can also be prepared from diester carboxylic acids of Formula Sb after modification of the carboxylic acid functional group to the

appropriate Y and Z group. A copper (I)-catalyzed coupling of malonates of Formula 7 with orthobromocarboxylic acids of Formula 8a (see A. Bruggink, A. McKillop, Tetrahedron, (1975), 31, 2607) can be used to prepare compounds of Formula 5b as shown in Scheme 3. Methods to prepare compounds of Formula 8a are common in the art (see P. Beak, V. Snieckus,Acc. Chem. Res., (1982), 15, 306 and Org. React., (1979), 26, 1 and references therein).

Scheme 3 Y RO2C CO2R z \J z X 7 ° C' I OR OR 8 CuI, base 5a R = C1-C4 alkyl f BEzC02H CIalit Oc ,k,< RO2C C02R OR OR 8a 7 5b R = C1-C4 alkyl Additionally, the malonate esters of Formula 5a can be prepared by treating aryl acetic acid esters of Formula 9 with a dialkyl carbonate or alkyl chloroformate in the presence of a suitable base such as, but not limited to, sodium metal or sodium hydride (Scheme 4). For example, see J. Am. Chem. Soc., (1928), 50, 2758.

Scheme 4 0 RO OR òr E/ H2CsCf o ~ O J/ H 0 C I CI'C OR OR OR base 9 R = C1-C4 alkyl Esters of Formula 9 can be prepared from acid-catalyzed alcoholysis of aryl acetonitriles of Formula 10 or esterification of aryl acetic acids of Formula 11 as illustrated in Scheme 5 (see Org. Synth., Coll. Vol. I, (1941), 270).

Additionally, esters of formula 9 can be prepared by palladium (0)-catalyzed cross coupling reaction of aryl iodides of Formula 8 with a Reformatsky reagent or an alkoxy(trialkylstannyl)acetylene followed by hydration (Scheme 5). For example, see T. Sakamoto, A. Yasuhara, Y. Kondo, H. Yamanaka, Synlett, (1992), 502, and J. F. Fauvarque, A. Jutard, J. Organometal. Chem., (1977), 132, C17.

Scheme 5 ROH ROH z I I H2Cs acid H2 &O acid H2CXCv O OR OH 10 9 11 BrZnCH2CO2R or 1 (I) R3SnC=COR (1) R3SnC-COR | (2) H+ Ew XZ 8 R = Cl-C4 alkyl

Aryl acetic acid esters of Formula 9a can also be prepared by copper (I)-catalyzed condensation of aryl halides of Formula 12 with compounds of Formula 13 as described in EP-A-307,103 and illustrated below in Scheme 6.

Scheme 6 R = C1-C4 alkyl Y = O, S, OCHR15, SCHR15, O-N=C(R7), NR15 Some esters of Formula 9 (Formula 9b) can also be prepared by forming the Y2 bridge using conventional nucleophilic substitution chemistry (Scheme 7). Displacement of an appropriate leaving group (Lg) in electrophiles of Formula 15 or 16 with a nucleophilic ester of Formula 14 affords compounds of Formula 9b. A base, for example sodium hydride, is used to generate the corresponding alkoxide or thioalkoxide of the compound of Formula 14.

Scheme 7 Lg-Z or 26 15 y2 E Lg-CHR1Z; E' 7 H2C, o 16 H2CXCv base MO OR OR 14 9b R = Cl-C4 alkyl R26 = OH, SH, CHR15OH, CHRI5SH, NHRl5 y2 = o, S, OCHR15, SCHR15, CHR150, CHR15S, NR15 Lg = Br, Cl, I, OS02CH3, OSO2(4-Me-Ph) Some esters of Formula 9 (Formula 9e) can also be prepared by forming the Y3 bridge from substituted hydroxylamine 9d and carbonyl compounds 14a. The

hydroxylamine 9d is in turn prepared from esters 9c. This method has been described in EP-A-600,835 and illustrated in Scheme 8.

Scheme 8 9c B=CHR15Br R = Cl-C4 alkyl 9d B = CHR15ONH2.HCI Y3 = CHR150N=C(R7) 2) Displacement and Conjugate Addition/Elimination Procedures Compounds of Formula I can also be prepared by reaction of Formula 17 compounds with alkali metal alkoxides (R10-M+), alkali metal thioalkoxides (R1S-M+), or an amine derivative in a suitable solvent (Scheme 9). The leaving group Lgl in the amides of Formula 17 are any group known in the art to undergo a displacement reaction of this type. Examples of suitable leaving groups include chlorine, bromine, and sulfonyl and sulfonate groups. Examples of suitable inert solvents are dimethylformamide or dimethyl sulfoxide, dimethoxyethane methanol.

Scheme 9 Y z E Z Ew XZ E Z R1O- M+, R1S-M+, G NH, R1NH2, X < alkyl), t A-N (C1-C6 alko)NH2, A-N \R2 or RlNH(C1-C6 alko) \R2 17 X@OR SR1, NH2, NHRl, I N(C1-C6 alkyl)R , NH(C1-C6 alkoxy), or N(C1-C6 alkoxy)Rl Lg1 = Cl, Br, -SO2V, or -OSO2V V= Cl-C6 alkyl, Cl-C6 haloalkyl, or 4-CH3-C6H4 M = K or Na Compounds of Formula 17a can be prepared from compounds of Formula lb (compounds of Formula 1 wherein X is OH) by reaction with halogenating agents such as thionyl chloride or phosphorus oxybromide to form the corresponding -halo-substituted derivatives (Scheme 10). Alternatively, compounds of Formula lb can be treated with an alkylsulfonyl halide or haloalkylsulfonyl anhydride, such as methanesulfonyl chloride, p-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding -alkylsulfonate of Formula 17a. The reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine).

Scheme 10 Y Y z E Z halogenating agent HO ,G<W on VSO2-hal on G y-' t w As; or VSO2-hal or ¼;;' A-N VSO2-O-O2SV A-N R2 W lb 17a Lg2 = Cl, Br, or -OSO2V V = C1-C6 alkyl, C1-C6 haloalkyl, or 4-CH3-C6H4 hal=Br,ClorF As illustrated in Scheme 11, sulfonyl compounds of Formula 17b can be prepared by oxidation of the corresponding thio compound of Formula 18 using well-known methods for the oxidation of sulfur (see Schrenk, K. In The Chemistry of Sulphones and Sulphoxides; Patai, S. et al., Eds.; Wiley: New York, 1988). Suitable oxidizing reagents include meta-chloro-peroxybenzoic acid, hydrogen peroxide and Oxone R (KHS05).

Scheme 11 Y Y E \ E z oxidi2ing agent VS GtO VS02 G G VS02 O A-N A-N \K2 18 17b V = Cl -C6 alkyl, Cl -C6 haloalkyl, or 4 CH3-C6H4 Alternatively, halo-compounds of Formula 17c (compounds of Formula 17a wherein A = N, G = N, and W = 0) can be prepared from hydrazides of Formula 19 as illustrated in Scheme 12. When R27 = C(=S)S(C1-C4 alkyl), the diacyl compound of Formula 19 is treated with excess thionyl halide, for example excess thionyl chloride.

The product formed first is the ring-closed compound of Formula 20 which can be isolated or converted in situ to the compound of Formula 17c; see P. Molina, A.

Tárraga, A. Espinosa, Synthesis, (1989), 923 for a description of this process.

Alternatively, when R27 = R2 as defined above, the hydrazide of Formula 19 is cyclized with phosgene to form the cyclic urea of Formula 17c wherein hal = Cl. This procedure is described in detail in J. Org. Chem., (1989), 54, 1048.

Scheme 12 Y Y E Z z °<czNH R27 = ¼=S)S(ci-¼ alkyl) HN oR27 ,R27 S(O)(hal)2 HN N N N 27 2 20 19 R27-R2 R27,R2 R27 = C(=S)S(C1-C4 alkyl) CO( XS(O)(hal)2 orR2 COC12 Y E Z hal f Nt ° N 17c hai=CI.Br.I The hydrazides of Formula 19 can be prepared as illustrated in Scheme 13.

Condensation of the isocyanate of Formula 21 with the hydrazine of Formula H2NNR2R27 in an inert solvent such as tetrahydrofuran affords the hydrazide.

Scheme 13 R27 = C(=S)S(CI-C4 alkyl) or R2 3) Conjugate Addition/Cyclization Procedures In addition to the methods disclosed above, compounds of Formula I wherein X = SR1 and G = C (Formula Ic) can be prepared by treating a ketenedithioacetal of

Formula 22 with an ambident nucleophile of Formula 6 (Scheme 14). The nucleophiles of Formula 6 are described above.

Scheme 14 R=C1-C4alkyl Ketene dithioacetals of Formula 22a can be prepared by condensing arylacetic acid esters of Formula 9 with carbon disulfide in the presence of a suitable base, followed by reaction with two equivalents of an R1-halide, such as iodomethane or propargyl bromide (Scheme 15).

Scheme 15 E Z I) CS2, base E R1S cO 2) ° 1R 2)2equiv.R1-hal SRI OR OR SR1 OR hal = Cl, Br or I 9 R = C1-C4 alkyl 22a Compounds of Formula id (compounds of Formula 1 wherein A = N, G = N) can be prepared by condensation of N-amino-ureas of Formula 23 with a carbonylating agent of Formula 24 (Scheme 16). The carbonylating agents of Formula 24 are carbonyl or thiocarbonyl transfer reagents such as phosgene, thiophosgene, diphosgene (ClC(=O)OCCl3), triphosgene (C13COC(=O)OCC13), N,N'-carbonyldiimidazole, N,N'-thiocarbonyldiimidazole, and 1,1'-carbonyldi(1,2,4-triazole). Alternatively, the compounds of Formula 24 can be alkyl chloroformates or dialkyl carbonates. Some of these carbonylating reactions may require the addition of a base to effect reaction.

Appropriate bases include alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, tertiary amines such as triethylamine and triethylenediamine, pyridine, or 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU). Suitable solvents include polar aprotic solvents such as acetonitrile,

dimethylformamide, or dimethyl sulfoxide; ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons such as toluene or benzene; or halocarbons such as dichloromethane or chloroform. The reaction temperature can vary between 0°C and 1500C and the reaction time can be from 1 to 72 hours depending on the choice of base, solvent, temperature, and substrates.

Scheme 16 xl II E TCT2 z 24 C« optional base X~(NtW $ H2N-N kz \R2 R Id 23 id T1 and T2 are independently CI OCC13, O(C1-C4 alkyl), l-imidazolyl, 1,2,4-tliazolyl X = OHor SH X1= Oor S N-Amino-ureas of Formula 23 can be prepared as illustrated in Scheme 17.

Treatment of an arylamine of Formula 25 with phosgene, thiophosgene, N,N'-carbonyldiimidazole, or N,N'-thiocarbonyldiimidazole produces the isocyanate or isothiocyanate of Formula 26. A base can be added for reactions with phosgene or thiophosgene. Subsequent treatment of the iso(thio)cyanate with an R2-substituted hydrazine produces the N-amino-urea of Formula 23.

Scheme 17 CWC 12, or w N#N N E Z E Z NH2 N optional base ¼NW 25 26 Y N E Z R2- NH-NH2 HN\ w C H2N-- N R2 23 Compounds of Formula 1 e (compounds of Formula 1 wherein A = CR5, G = N, and X = 0) can be prepared by either method illustrated in Scheme 18. Ureas of Formula 27 are reacted with activated 2-halocarboxylic acid derivatives such as 2-halocarboxylic acid chlorides, 2-halocarboxylic acid esters or 2-haloacyl imidazoles.

The initial acylation on the arylamino nitrogen is followed by an intramolecular displacement of the 2-halo group to effect cyclization. Base may be added to accelerate the acylation and/or the subsequent cyclization. Suitable bases include triethylamine and sodium hydride. Alternatively, Formula le compounds can be prepared by reaction of Formula 26 isocyanates with Formula 28a esters. As described above, base may be added to accelerate the reaction and subsequent cyclization to Formula le compounds.

Scheme 18 0 N II E/Yz TC\CIS -hal 28 HN Cz HN R2 optional base 27 y T = Cl, O(C1-C4 alkyl), or hal = C1, Br, or I R5 R2 R2NHCHR5C(O)OR le 28a Y / E Z optional base NRW w R=C1-C4alkyl 26 The ureas of Formula 27 can be prepared by either of the methods illustrated in Scheme 19. The arylamine of Formula 25 can be contacted with an isocyanate or isothiocyanate of Formula R2N=C=W as described above. Alternatively, an isocyanate or isothiocyanate of Formula 26 can be condensed with an amine of Formula R2-NH2 to form the urea. The arylamine and iso(thio)cyanates of Formulae 25 and 26, respectively, are commercially available or prepared by well-known methods. For example, isothiocyanates can be prepared by methods described in J. Heterocycl. Chem., (1990), 27, 407. Isocyanates can be prepared as described in March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), pp 944, 1166 and also in Synthetic Communications, (1993), 23(3), 335 and references therein. For methods describing the preparation of arylamines of Formula 25 that are not commercially available, see M. S.

Gibson In The Chemistry of the Amino Group; Patai, S., Ed.; Interscience Publishers, 1968; p 37 and Tetrahedron Lett. (1982), 23(7), 699 and references therein.

Scheme 19 4) Thionation Procedures Compounds of Formula Ie, compounds of Formula I wherein W = S, can be prepared by treating compounds of Formula Id (I wherein W = 0) with thionating reagents such as P2S5 or Lawesson's reagent (2,4-bis(4-methoxyphenyl)- 1,3-dithia-2,4- diphosphetane-2,4-disulfide) as illustrated in Scheme 20 (see Bull. Soc. Chintz. Belg., (1978), 87, 229; and Tetrahedron Lett., (1983), 24, 3815).

Scheme 20 Z P2Sg or N X lo Lawesson's reagent X G lawesson's reagent S 0 A-N A-N \R2 R2 Id Ie 5) Aryl Moiety (E-Y-Z) Synthesis Procedures Compounds of Formula If (compounds of Formula I wherein Y is CHR 150, CHR15S, or CHRlfo-N=CR7) can be prepared by contacting halides of Formula 29 with various nucleophiles (Scheme 21). The appropriate alcohol or thiol is treated with a base, for example sodium hydride, to form the corresponding alkoxide or thioalkoxide which acts as the nucleophile.

Scheme 21 Ez CHRI 5(CI, Br, orl) HO-Z, or 7 'vaN E HON=CR7-Z, or I HS-Z; base A-N A-N R2 R2 29 If Yt= CHR1SO, CHR15ON=CR7, CHR15S off Halogenation CHR1SOH Ez G xy',,yw A-N R2 30 Some aryl halides of Formula 29 can be prepared by radical halogenation of the corresponding alkyl compound (i.e., H instead of halogen in Formula 29), or by acidic cleavage of the corresponding methylether (i.e., OMe instead of halogen in Formula 29).

Other aryl halides of Formula 29 can be prepared from the appropriate alcohols of Formula 30 by well known halogenation methods in the art (see Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry; 3rd ed., Part B, Plenum: New York, (1990), p 122).

Compounds of Formula I wherein Y is CR6=CR6 or CHR6-CHR6 (Formula Ig and Ih, respectively) can be prepared as illustrated in Scheme 22. Treatment of the halides of Formula 29 with triphenylphosphine or a trialkylphosphite produces the corresponding phosphonium salt (Formula 31) or phosphonate (Formula 32), respectively.

Condensation of the phosphorus compound with a base and a carbonyl compound of Formula Z(R6)C=O affords the olefin of Formula Ig.

Scheme 22 EzCHR6(CI, Br, or I) zCHR6-P P(C6Hs)3 or G G P(OR)3 A-N R2 R2 R2 29 31: P1 =P+(C6H5)3 halide- 0 R=C1-C4alkyl 32: P1=P(OR)2 O=C(R6)Z sCR6=CR6Z base G C A--N H2 \K2 1) Halogenation Ig Ig L 2) Dehalogenation Catalyst CR6- CHR6- Z C-- Z z C==- C- Z X C,8 tW X A-N R2 w Ih Ii

The olefins of Formula Ig can be converted to the saturated compounds of Formula Ih by hydrogenation over a metal catalyst such as palladium on carbon as is well-known in the art (Rylander, Catalytic Hydrogenation in Organic Synthesis; Academic: New York, 1979).

Formula Ii alkynes can be prepared by halogenationldehalogenation of Formula Ig olefins using procedures well-known in the art (March, J. Advanced Organic Chemistl-),; 3rd ed., John Wiley: New York, (1985), p 924). Additionally, Formula Ii alkynes can be prepared by well-known reaction of aryl halides with alkyne derivatives in the presence of catalysts such as nickel or palladium (see J. Organomet. Chenz., (1975), 93 253-257).

The olefin of Formula Ig can also be prepared by reversing the reactivity of the reactants in the Wittig or Horner-Emmons condensation. For example, 2-alkylaryl

derivatives of Formula 33 can be converted into the corresponding dibromo-compound of Formula 34 as illustrated in Scheme 23 (see Synthesis, (1988), 330). The dibromo- compound can be hydrolyzed to the carbonyl compound of Formula 35, which in turn can be condensed with a phosphorus-containing nucleophile of Formula 36 or 37 to afford the olefin of Formula Ig. Additionally, compounds of Formula 35 can be prepared by oxidation of the corresponding alcohols of Formula 30.

Vinylhalides of Formula Ij can be prepared by reacting phosphorus reagents of Formulae 37a or 37b with carbonyl compounds of Formula 35 (Scheme 23). The preparations of halides of Formula 37a from the appropriate diethylphosphonoacetate are described by McKenna and Khawli in J. Org. Chem., (1986), 51, 5467. The thiono esters of Formula 37b can be prepared from esters of Formula 37a by converting the carbonyl oxygen of the ester to a thiocarbonyl (see Chem. Rev., (1984), 84, 17 and Tetrahedron Lett., (1984), 25, 2639).

Scheme 23 1) Br or NBS CR 2 equiv., CC14 zCR6J E light CCl4 light G Morpholine C W G9W 2)Morpholine H20 w Con. HCI, H20 A-N NBS = N-bromosuccinimide A-N R2 33 34: 51 = Br (C6Hs)3P=c(R6)z/ 34: 51=(=0) Base Base hal or 1;r (R0)2P-CHC-OZ E' /P I 37a: J2 = C I - G M 37a: J2=O 37b: J2=S A-N R6 J2 XR2 I II Ig C=C-C-OZ hal C R=C1-C4alkyl xy;;w J2=O,S A-N hal=F,CI,Br,I R2 Ij

Oximes of Formula Ik (Formula I wherein Y is C(R7)=N-O) can be prepared from carbon compounds of Formula 38 by condensation with hydroxylamine, followed by O-alkylation with electrophiles of Formula Z-(Cl, Br, or I) (Scheme 24). Alternatively, the O-substituted hydroxylamine can be condensed with the carbonyl compound of Formula 38 to yield oximes of Formula Ik directly.

Scheme 24 1) 1) H2N-OH sCR7=N-oZ 2) Z-hal G 2) Hal U w or A--N H2N-OZ A-N \R2 R2 38 hal = Cl, Br or I Ik Carbamates of Formula Il can be prepared by reacting aryl alcohols of Formula 30 with isocyanates of Formula 39 (Scheme 25). A base such as triethylamine can be added to catalyze the reaction. As shown, carbamates of Formula I1 can be further alkylated to provide the carbamates of Formula Im.

Scheme 25 0 zCHR15OH ZNCO /CHR150 NHZ 39 E U I XY;; yW x-U w A-N A-N k2 30 11 0 R15-hal E R15 U base hal = C 1, Br or I A-N R2 Im Compounds of Formula I wherein Y is -CHRl50-N=C(R7)-C(=N-A2-Zl)-Al-, -CHR1 5O-N=C(R7)-C(R7)=N-A2-A3- or -CHR150-N=C(-C(R7)=N-A2-Zl)- can be prepared by methods known in the art or obvious modifications (see, for example, WO 95/18789, WO 95/21153, and references therein) together with the methods disclosed herein.

Compounds of Formula I wherein Y is -CHR15OC(=O)O-, -CHR15OC(=S)O-, -CHR150C(=O)S-, -CHR150C(=S)S-, -CHR15SC(=o)N(R 15), -CHR15SC(=S)N(R15)-, -CHR15SC(=O)O-, -CRR15SC(=S)O-, -CHR15SC(=O)S-, -CHR15SC(=S)S-, -CHR15SC(=NR15)S- or -CHR15N(R15)C(=O)N(R15)- can be prepared by methods known in the art or obvious modifications (see, for example, U.S. 5,416,110, EP 656,351 and references therein) together with the methods disclosed herein.

The compounds of the present invention are prepared by combinations of reactions as illustrated in the Schemes 1-25 in which Z is a moiety as described in the summary.

Preparation of the compounds containing the radical Z as described in the summary, substituted with L (defined as any group attached to Z as depicted in each of the individual schemes) can be accomplished by one skilled in the art by the appropriate combination of reagents and reaction sequences for a particular Z-L. Such reaction sequences can be developed based on known reactions available in the chemical art. For

a general reference, see March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985) and references therein. See the following paragraphs for some examples of how L is defined in individual schemes, and the preparation of representative Z-L examples.

Compounds of Formula 41 in Scheme 26 can be prepared from compounds of Formula 40 by reaction with hydroxylamine or hydroxylamine salts. See Sandler and Karo, "Organic Functional Group Preparations," Vol. 3 Academic Press, New York, (1972) 372-381 for a review of methods. Compounds of Formula 41 correspond to compounds of Formula 13 in Scheme 6 when Y1 = O-N=C(R7) and in Scheme 21, reagent HO-N=CR7.

Scheme 26 Compounds of Formula 40 can be prepared from compounds of Formula 39a (Scheme 27) by Friedel-Crafts acylation with compounds of Formula 42. (See Olah, G.

"Friedel-Crafts and Related Reactions," Interscience, New York (1963-1964) for a general review). Compounds of Formula 40 may also be prepared by reaction of acyl halides, anhydrides, esters, or amides of Formula 45 with organometallic reagents of Formula 44. (See March, J. Advanced Organic Chemists!; 3rd ed., John Wiley: New York, (1985), pp 433-435 and references therein.) The organometallic compounds of Formula 44 may be prepared by reductive metallation or halogen-metal exchange of a halogen-containing compound of Formula 43 using, for example, magnesium or an organolithium reagent, or by deprotonation of compounds of Formula 39a using a strong base such as a lithioamide or an organolithium reagent, followed by transmetallation.

Compound 40 corresponds to Compound 14a in Scheme 8, while compound 40a corresponds to O=C(R6)Z in Scheme 22.

Scheme 27 Z-H R28COCI (42) AIC13 40 R28=R7 39a 40a R28=R6 0--CR28-T3 Z-hal Z-M 1 O=CR28-z 43 Z-M1 40 40 R28=R7 44 40a R28=R6 hal=Cl, Br, I Ml=MgX T3=C1 CuLiZ OCOR28 CdZ OR SnR3 NR2 R=C1-C4aikyl R28 = R6 or R7 Compounds of Formula 43 may be prepared by reaction of compounds of Formula 39a (Scheme 28) with, for example, bromine or chlorine, with or without additional catalysts, under free-radical or aromatic electrophilic halogenation conditions, depending on the nature of Z. Alternative sources of halogen, such as N- halosuccinimides, tert-butyl hypohalites or S02C12, may also be used. (See March, J.

Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), pp 476-479, 620-626, and references therein.) For a review of fi-ee-radical halogenation, see Huyser, in Patai," The Chemistry of the Carbon-Halogen Bond," Part I, Wiley New York (1973) pp 549-607. For electrophilic substitutions, see de la Mare, "Electrophilic Halogenation," Cambridge University Press, London (1976). Compounds of Formula 43 correspond to compounds of Formula 15 in Scheme 7 where Lg = Br, Cl, or I and reagent Z-hal in Scheme 24. Compounds of Formula 47 can be prepared from compounds of Formula 46 by similar procedures. Compounds of Formula 47 correspond to compounds of Formula 16 in Scheme 7 where Lg = Br, Cl, or I. Compounds of Formula 36 or 37 in Scheme 23 can be prepared by reaction of compounds of Formula 47 with triphenylphosphine or trialkyl phosphites, respectively, followed by deprotonation with base. See Cadogen, "Organophosphorus Reagents in Organic Synthesis," Academic Press, New York (1979) for a general treatise on these reagents.

Scheme 28 0 XN-hal Z-H hal2, ,or$1oh,:ir on t-BuO-hal Z-hal 39a > 43 or S02Cl2 optional catalyst hal = Cl, Br, I H-CHR6-Z , hal-CHR6-Z 46 47 I ) (C6H5)3P ol (RO)3p 2) base R = C1-C4 alkyl 36 or 37 in Schere 23 Compounds of Formula 48 can be prepared from compounds of Formula 40b by treatment with peracids such as perbenzoic or peracetic acid, or with other peroxy compounds in the presence of an acid catalysts, followed by hydrolysis of the resultant ester. For a review, see Plesnicar, in Trahanovsky, "Oxidation in Organic Chemistry, pt.

C, Academic Press, New York (1978) pp 254-267. Formula 48 corresponds to Formula 13 in Scheme 6 when Yl = 0 and reagent HO-Z in Scheme 21. Compounds of Formula 52 can be prepared from compounds of Formula 48 by conversion to the dialkylthiocarbamates of Formula 50 followed by rearrangement to Formula 51 and subsequent hydrolysis. See M. S. Newman and H. A. Karnes, J. Org. Chem. (1966), 31 3980-4. Formula 52 corresponds to Formula 13 in Scheme 6 when Yl = S and reagent HS-Z in Scheme 21.

Scheme 29 O=C(CH3}Z 1) [o] HOZ HO-Z 40b 2) hydrolysis 48 ClCSN(R)2 ZO-CSN(R)2 heat > ZS-CON(R)2 > HS-Z 49 50 5l 52 R = C1-C4 alkyl Compounds of Formula 53 can be converted to compounds of Formulae 43, 48 or 52 via the diazonium compounds 54, by treatment with nitrous acid followed by subsequent reaction (Scheme 30). See reviews by Hegarty , pt. 2, pp 511-91 and Schank, pt. 2, pp 645-657, in Patai, "The Chemistry of Diazonium and Diazo Groups," Wiley, New York (1978). Treatment of Formula 54 compounds with cuprous halides or iodide ions yield compounds of Formula 43. Treatment of Formula 54 compounds with cuprous oxide in the presence of excess cupric nitrate provides compounds of Formula 48. (Cohen, Dietz, and Miser, J. Org. Chem., (1977), 42, 2053). Treatment of Formula 54 compounds with (S2)2 yields compounds of Formula 52.

Scheme 30 Z-NH2 HNO2 Z-N2+ CuBr, CuCI or I 53 54 Z-hal hal=Br, Cl, I 43 Cu20 H&Z Cn(N03)2 48 (s2)-2 HS-Z 52 Compounds of Formula 53 can be prepared from compounds of Formula 39a by nitration, followed by reduction (Scheme 31). A wide variety of nitrating agents is available (see Schofield, " Aromatic Nitration," Cambridge University Press, Cambridge (1980)). Reduction of nitro compounds can be accomplished in a number of ways (see March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985),

pp 1103-4 and references therein). Formula 53 corresponds to Formula 13 in Scheme 6 when yl = NR15 and R15 = H.

Scheme 31 Iodides of Formula 8 can be prepared from compounds of Formula 58 by the methods described above in Schemes 21-25 for various Y-Z combinations. Compounds of Formula 58 can in turn be prepared from compounds of Formula 57 by functional group interconversions which are well known to one skilled in the art. The compounds of Formula 57 can be prepared by treating compounds of Formula 56 with an organolithium reagent such as n-BuLi or LDA followed by trapping the intermediate with iodine (Beak, P., Snieckus, V. Acc. Chem. Res., (1982), 15, 306). Additionally, lithiation via halogen metal exchange of compounds of Formula 56, where H is replaced by Br, will produce an intermediate which can be trapped with iodine to prepare compounds of Formula 57 (Parham, W. E., Bradsher, C. K. Acc. Chem. Res., (1982), 15, 300 (Scheme 32).

Scheme 32 Organolithiuin z T4 T5 I reagent, E Functional F H I2 I Group 1 56 57 Interconversion 5X YZ construction T4 = C02H, CONR2, CONHR, Y\Z 93 8 R H3C 8 N (CRNR2, T5 = CHR6(CI, Br, I), CHO N CH2OH,OH R R= C1-C4 alkyl CH2OH, OMe, OCH2OMe t =1 or 2

Compounds of Formula In (Formula IA where Y is (CH2)xO, where x = O or 1) can be prepared by contacting hydroxy compounds of Formula 59 with appropriate heterocycles or activated aromatic hydrocarbons Lg-Z (where Lg is an appropriate leaving group, for example, halogen or alkylsulfonyl) in the presence of suitable bases (for example, K2C03, KO-t-Bu or NaH) in suitable solvents (for example, acetone, dimethylformamide, dimethyl sulfoxide or tetrahydrofuran) (see Scheme 33).

Scheme 33 OH Oz E (CH2)x F (CH2)x LfZ G solvent ¼; ¼W A-N A-N k2 59 where x = 0 or 1 In Compounds of Formula Lg-Z may be prepared according to literature procedures, for example, Comprehensive Heterocyclic Chemistry, Pergamon Press, vol. 6, 1984, pp 463-511 or J. Org. Chem. (1973), 38, 469 or J. Het. Chem. (1979), 961 for the preparation of 1,2,4-thiadiazoles, U.S. 5,166,165 or J. Chem. Soc., Perkin Trans. 1 (1983), 967 for the preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles, EP 446,010 or J. Med. Chem. (1992), 35, 3691 for the preparation of 1,2,4-oxadiazoles.

Additionally, when Z is substituted with iodine or Lg2 from Scheme 10, R9 may be introduced via a palladium(0) catalyzed cross coupling reaction with the appropriate nucleophile containing R9, such as arylboronic acids, aryl or alkyl zinc reagents, and substituted acetylenes.

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform

additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula I. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula I.

One skilled in the art will also recognize that compounds of Formula I and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated.

1H NMR spectra are reported in ppm downfield from tetramethylsilane; s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = doublet of doublets, br = broad, br s = broad singlet.

EXAMPLE 1 Step A: Preparation of N-(2-methoxyphenyl)-2,2-dimethylhydrazinecarboxamide To a stirred solution of 15.0 g of 2-methoxyphenyl isocyanate in 100 mL of toluene at 5 "C under nitrogen was slowly added 7.65 mL of 1,1-dimethyWydrazine in 10 mL toluene. The cooling bath was then removed and the reaction was allowed to stir for an additional 10 min, and was then concentrated under reduced pressure. The resulting material was dissolved in diethyl ether and concentrated again. A solid was obtained which was triturated with hexanes to afford 21 g of the title compound of Step A as a white solid. 1H NMR (CDC13) 6 8.6 (br s,lH), 8.24 (m,lH), 6.95 (m,2H), 6.85 (m,lH), 5.35 (br s,lH), 3.89 (s,3H), 2.60 (s,6H).

Step B: Preparation of 5-chloro-2\4-dihydro-4-(2-methoxyphenyl)-2-methyl-3H- 1 2,4-triazol-3-one To a stirred solution of 21 g of the title compound of Step A in 800 mL of dichloromethane under nitrogen was added 29.85 g of triphosgene. The reaction was heated to reflux and allowed to reflux overnight, cooled, and then concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with distilled water, and then with saturated aqueous sodium chloride solution. The organic layer was dried (MgS04), filtered, and concentrated under reduced pressure. The solid

was recrystallized from dichloromethane and the resulting solid was triturated with diethyl ether to afford 10 g of the title compound of Step B as a white solid melting at 152-154 "C. 1H NMR (CDC13) 6 7.45 (t,lH),7.25 (d,lH), 7.05 (m,2H), 3.84 (s,3H), 3.53 (s,3H).

Step C: Preparation of 5-chloro-24-dihydro-4-(2-hydroxyphenyl)-2-methyl- 3H- 1 2,4-triazol-3-one The title compound of Step B (7.7 g) was dissolved in 65 mL of dichloromethane under nitrogen, cooled to -78 "C, and 34 mL of a 1.0 M boron tribromide solution in dichloromethane was then added over 0.5 h with stirring. After the addition, the cooling bath (dry ice/acetone) was kept in place for an additional 0.5 h and then the reaction was allowed to warm to room temperature. Ice was added to the reaction mixture which was then diluted with diethyl ether and the product was extracted using 1N aqueous sodiunl hydroxide solution. The aqueous layer was acidified with 6N aqueous hydrochloric acid solution and extracted with dichloromethane and then with ethyl acetate. The organic layers were combined, dried (MgS04), filtered and concentrated under reduced pressure.

The resulting residue was triturated with diethyl ether to afford 5.54 g of the title compound of Step C as a white solid. H NMR (CDCl3) 6 8.18 (s, 1H), 7.11 (t,2H), 6.91 (t,lH), 6.76 (d,lH), 3.56 (s,3H).

Step D: Preparation of 2,4-dihydro-4-(2-hydroxyphenyl)-5-methoxy-2-methyl- 3H-1,2,4-triazol-3-one To a stirred solution of 5.54 g of the title compound of Step C in 50 mL of methanol and 25 mL of 1,2-dimethoxyethane under nitrogen was added 18.6 mL of 30% sodium methoxide solution in methanol. The reaction was heated at reflux for 5.5 h and then cooled to room temperature. The mixture was diluted with diethyl ether and the product was extracted using 1N aqueous sodium hydroxide solution. The aqueous layer was acidified with 6N aqueous hydrochloric acid solution and extracted with dichloromethane. The organic layer was dried (MgS04), filtered, and then concentrated under reduced pressure. The resulting residue was triturated with diethyl ether to afford 3.85 g of the title compound of Step D as a white solid (85% pure). 1H NMR (CDCl3) 6 8.40 (br s,lH), 7.20 (m,2H), 7.03 (d,lH), 6.94 (t,lH), 4.00 (s,3H), 3.48 (s,3H).

Step E: Preparation of 4-[2-[[3-[3 S-bis(flifluoromethyl)phenyll - 1 24-thiadiazol- 5-yll oxyiphenyll -2,4-dihydro-5-methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one To a solution of 5-chloro-3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-thiadiazol e (0.8 g, 2.4 mmol, available from Maybridge, Catalog No. RDR03892) in DMF (8 mL) was added the title compound of Step D (0.44 g, 2.4 mmol) at room temperature. The solution was cooled to 5 °C and potassium carbonate (0.33 g, 2.4 mmol) was added

followed by a catalytic amount of cuprous chloride (about 3-5 mg). The reaction mixture was stirred at room temperature for 4 h. The reaction was partitioned between water (30 mL) and ether (30 mL), and the aqueous layer was extracted twice with ether (25 mL). The combined ether layers were washed with water (30 mL), dried over anhydrous magnesium sulfate, and then concentrated to give 1.14 g of crude product.

Flash column chromatography (gradient elution with 30-50% ethyl acetate in hexane) gave the title compound of Step E, a compound of the invention, as a white solid (0.62 g) melting at 139.5-141.5 "C. 1H NMR (CDC13) 6 8.36 (s,2H), 7.94 (s,lH), 7.60 (m,2H), 7.50 (d,2H), 3.81 (s,3H), 3.37 (s,3H).

EXAMPLE 2 Step A: Preparation of ethyl 3 -(trifluoromethoxy )benzenecarboximidate hydrochloride To a solution of 3-(trifluoromethoxy)benzonitrile (10 g. 53.4 mmol) in ethyl ether (55 mL) is added absolute ethanol (3.3 mL). The solution is cooled to 0 °C and saturated with dry HCl gas. The reaction mixture is then left to stand at ambient temperature for 7 days after which time it is filtered under a stream of dry nitrogen to give the title compound of Step A (10.99 g) as a white solid. 1H NMR (Me2SO-d6) 6 8.2 (m,1H), 7.95 (d,lH), 7.83 (s,lH), 7.59 (m,lH), 4.66 (q,2H), 1.52 (t,3H).

Step B: Preparation of 3-(trifluoromethoxy)benzenecarboximidamide hydrochloride To a solution of the title compound of Step A (10.99 grams, 40.76 mmol) in methanol (15 mL) is added ammonia (8.2 mL, 7N solution in methanol). This mixture was stirred for 5 days before being concentrated to give the title compound of Step B (10.36 g). 1H NMR (Me2SO-d6) 9.4-8.8 (br,4H), 8.01 (m,lH), 7.97 (m,lH), 7.81 (m,2H).

Step C: Preparation of 5-chioro-3-[3-(trifluoromethoxyphenyl1- 1 2,4-thiadiazole To a solution of the title compound of Step B (10.36 g, 43.06 mmol) in water (100 mL) is added methylene chloride (200 mL), benzyltriethylammonium chloride (0.8 g) and perchloromethyl mercaptan (4.7 mL, 32.6 mmol) and the mixture is cooled in an ice bath. With efficient stirring, sodium hydroxide (6.89 g) in water (100 mL) is then added dropwise such that the internal temperature does not exceed 10 "C. After the addition is complete, the cooling bath is removed and the reaction mixture stirred for a further 1.5 h. The organic layer is then separated, dried over magnesium sulfate and concentrated. The yellow/brown tar is extracted with boiling hexane and the hot solution is filtered through a pad of silica gel. The silica gel is washed with hexane and the solution is then concentrated to a give the title compound of Step C as a yellow oil which

is used without further purification. 1H NMR (CDCl3) 6 8.18 (d,lH), 8.11 (s,1H), 7.49 (t,lH), 7.34 (m,lH).

Step D: Preparation of 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[3-[3- (trifluoromethoxy)phenyll- 1 ,2,4-thiadiazol-5-ylloxylphenyll-3H- 1,2,4- triazol-3-one To a solution of the title compound of Step D in Example 1 (71.44 g, 323.3 mmol) in DMF (680 mL) is added freshly ground potassium carbonate (93.9 g) and the title compound of Step C (95.5 g, 340 mmol). The mixture was stirred at ambient temperature for 3 days before being diluted with water and extracted with ethyl acetate. The aqueous phase was re-extracted with ethyl acetate and the combined organic layers were washed with water. The organic layer was dried over magnesium sulfate and concentrated. The material was purified by column chromatography (silica gel, 40%, then 60%, and then 80% ethyl ether in petroleum ether) followed by crystallization of the material from the concentrated fractions to yield 65g of the title compound of Step D, a compound of the invention, as an off white solid melting at 112-113 "C. 1H NMR (CDCl3) 68.10 (d,1H), 8.05 (s,lH), 7.6-7.4 (m,SH), 7.27 (m,1R), 3.79 (s,3H), 3.37 (s,3H).

EXAMPLE 3 Step A: Preparation of 2-(4-chlorophenyl)-5-(methylthio)- 1,3 4-oxadiazole To a solution of 4-chlorobenzoic hydrazide (15.0 g, 87.92 mmol) in ethanol (133 mL) and water (10 mL) is added potassium hydroxide (5.18 g, 92.3 mmol) and carbon disulfide (5.82 mL) in a dropwise fashion. The mixture was further diluted with ethanol (88 mL) and the mixture is heated at reflux overnight. Methyl iodide (6.02 mL) is then added and the mixture is cooled in an ice bath and stirred for a further 0.5 h. The solution is concentrated and redissolved in methylene chloride. The solution is filtered through a pad of silica gel and concentrated to give the title compound of Step A (17.69 g) as a white solid.

Step B: Preparation of 2-A-chlornphenvl)-5-(methylsulfonvl )- 1 3,4-oxadiazole To a solution of the title compound from Step A (17.69 g, 78.1 mmol) in acetic acid (156 mL) was added a solution of potassium permanganate (25.92 g, 164.01 mmol) in water (547 mL) in a dropwise fashion. A slight exotherm was controlled with an ice bath. On complete addition, sodium hydrosulfite (80 mL, 40% aqueous solution) was added and the resultant precipitate was filtered to give the title compound of Step B.

1H NMR (CDCl3) 6 8.70 (m,2H), 7.57 (m,2H), 3.53 (s,3H).

Step C: Preparation of 4- [2- [[5-(4-chlorophenyl)- 13 ,4-oxadiazol-2- yl]oxy]phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triaz ol-3-one To a solution of the title compound of Step D in Example 1 (0.5 g, 2.26 mmol) in acetone (5 mL) was added potassium carbonate (406 mg) and the title compound of Step B (585 mg). The mixture was stirred overnight before being diluted with methylene chloride and washed with water. The aqueous phase was re-extracted with methylene chloride and the combined organic phases were dried over magnesium sulfate and the solution was concentrated under reduced pressure. The resulting solid was triturated with ethyl ether to give the title compound of Step C (719 mg, 80 %), a compound of the invention, as a solid melting at 130-132 "C. 1H NMR (CDCl3) 5 7.92 (d,2H), 7.85 (d,lH), 7.6-7.4 (m,5H), 3.88 (s,3H), 3.43 (s,3H).

EXAMPLE 4 Preparation of 2,4-dihydro-4-[2-[3-iodo-1,2,4-thiadiazol-5-yl)oxy]phenyl]-5 -methoxy- 2-methyl-3H- 1 ,2,4-triazol-3-one To a solution of the title compound of Step Din Example 1 (3.0 g, 13.6 mmol) in acetone (27 mL) was added potassium carbonate (2.44 g) and 3-iodo-5-(methylsulfonyl)- 1,2,4-thiadiazole (J. Org Chem. (1973), 38, 469) (4.33 g). The mixture was stirred at ambient temperature for 36 h before being diluted with water. The resulting mixture was extracted twice with methylene chloride and the combined extracts were dried over magnesium sulfate. The solution was concentrated to a solid which was triturated with hot ethanol to give the title compound of Example 4 (2.8 g, 48%), a compound of the invention. 1H NMR (CDCl3) 5 7.55 (m,2H), 7.46 (m,2H), 3.86 (s,3H), 3.40 (s,3H).

EXAMPLE 5 Preparation of 4- [2-[ [3-(3 3-dimethyl- 1 -butynyl)- 1 ,2,4-thiadiazol-5-ylloxylphenyll-2 ,4- dihydro-5-methoxy-2-methyl-3H- 1,2,4-triazol-3-one To a solution of the title compound of Example 4 (307 mg, 0.71 mmol) in DMF (4 mL) was added copper(I) iodide (14 mg), triethylamine (0.347 mL), 3,3-dimethyl-l- butyne (0.219 mL) and bis(triphenylphosphine)palladium(II) chloride (25 mg). The mixture was stirred for 40 h at ambient temperature before being diluted with ethyl acetate, washed with 1N HCl and dried over magnesium sulfate. The solution was concentrated and purified by column chromatography (silica gel, 80 % ethyl ether in petroleum ether) to give the title compound of Example 5, a compound of the invention.

1H NMR (CDCl3) 5 7.55 (m,2H), 7.45 (m,2H), 3.83 (s,3H), 3.39 (s,3H), 1.32 (s,9H).

EXAMPLE 6 Preparation of 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[3-[3- [(trimethylsilyl)ethynyl]phenyl]-1,2,4-thiadiazol-5-yl]oxy]p henyl]-3H-1,2,4-triazol-3-one To a solution of 2,4-dihydro-4-[2- [[3-(3-iodophenyl)- 1,2,4-thiadiazol-5- yl]oxy]phenyl]-5-methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one (prepared from 3-iodobenzonitrile according to the procedure described in Example 2) (1.0 g, 1.97 mmol) in DMF (4 mL) was added copper(I) iodide (38 mg), triethylamine (0.96 mL), (trimethylsilyl)acetylene (0.70 mL) and bis(triphenylphosphine)palladium(II) chloride (35 mg). The mixture was stirred overnight at ambient temperature before being diluted with ethyl ether. The resulting mixture was washed with a saturated aqueous solution of ethylenediaminetetraacetic acid, a saturated aqueous solution of NaRCO3, and a saturated aqueous solution of NaCI and then was dried over magnesium sulfate. The solution was concentrated and the material was crystallized from ethanol to give the title compound of Example 6 (315 mg), a compound of the invention, as a solid melting at 133-134 °C. 1H NMR (CDC13) 6 8.27 (s,lH), 8.05 (d,lH), 7.65-7.5 (m,5H), 7.4 (t,lH), 3.77 (s,3H), 3.37 (s,3H), 0.26 (s,9H).

EXAMPLE 7 Preparation of 4-[2- [[3-(3-ethynylphenyl)- 1 ,2,4-thiadiazol-5-yl]oxy]phenyl] -2 «4-dihydro- 5-methoxy-2-methyl-3H- 1,2,4-triazol-3-one To a solution of the title compound of Example 6 (300 mg, 0.629 mmol) in methanol (3 mL) was added potassium carbonate (87 mg). The mixture was stirred at ambient temperature for 10 min before being diluted with water and extracted three times with methylene chloride. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. Recrystallization from ethanol afforded the title compound of Example 7 (153 mg), a compound of the invention, as a white solid melting at 177-178 °C. 1H NMR (CDC13) 6 8.29 (s,lH), 8.15 (d,lR), 7.62 (m,1R), 7.57 (m,2H), 7.49 (m,2H), 7.4 (t,lH), 3.78 (s,3H), 3.37 (s,3H).

EXAMPLE 8 Step A: Preparation of 3-(5-chloro-1,2,4-thiadiazol-3-yl)phenol To a solution of 3-chloro-5-(3-methoxyphenyl)- 1,2,4-thiadiazole (prepared from 3-methoxybenzonitrile according to the procedure described in Step C in Example 2) (11.4 g, 50.4 mmol) in methylene chloride (150 mL) was added boron tribromide (5.25 mL) with ice bath cooling. The reaction was allowed to warm slowly to ambient temperature. After 20 h, a saturated aqueous solution of NaRCO3 was added and the mixture was extracted with ethyl ether and the extract was dried over magnesium sulfate.

Purification by column chromatography (silica gel, 20% and then 40% ethyl ether in

petroleum ether) gives the title compound of Step A. H NMR (CDCl3) 6 7.85 (d, lH), 7.73 (s,1H), 7.36 (t,lH), 6.95 (d,lH), 5.42 (s,lH).

Step B: Preparation of [3-[5-[2-(1,5-dihydro-3-methoxy-1-methyl-5-oxo-4H- 1 ,2,4-triazol-4-vl)henoxvl- 1 ,2,4-thiadiazol-3-vlIphenvll benzoate To a solution of the title compound of Step A (7.15 g, 33.6 mmol) in methylene chloride (112 mL) was added triethylamine (6.1 mL), 4-(dimethylamino)pyridine (206 mg) and benzoyl chloride (4.5 mL) with ice bath cooling. The ice bath was removed and the mixture was stirred at ambient temperature for 15 min. HCl (1 N aqueous solution) was then added and the mixture was extracted with ethyl ether then with methylene chloride. The combined organic layers were dried over magnesium sulfate and concentrated to give a solid. To this solid was added the title compound of Step Din Example 1 (7.44 g), potassium carbonate (6.04 g) and acetone (150 mL). The mixture was stirred for 5 days before being diluted with water. The resulting mixture was extracted with methylene chloride and the extract was dried over magnesium sulfate.

Purification by column chromatography (silica gel, 1% and then 2% methanol in methylene chloride) gave the title compound of Step B (10.1g), a compound of the invention. H NMR (CDCl3) 88.21 (d,2H), 8.1 (d,2H), 7.7-7.4 (m,9H), 3.77 (s,3H) 3.37 (s,3H).

EXAMPLE 9 Preparation of 2,4-dihydro-4-[2-[[3-(3-hydroxyphenyl)-1 ,2 4-thiadiazol-5- yl]oxy]phenyl]-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one To a solution of the title compound of Step B in Example 8 (10.1 g, 20 mmol) in methanol (50 mL) was added sodium methoxide (1.306g). Ethanol (50 mL) and methylene chloride (25 mL) were then added and the mixture was stirred overnight. The mixture was acidified with HC1 (1 N aqueous solution) and was extracted twice with methylene chloride. The combined extracts were dried over magnesium sulfate.

Purification by column chromatography (silica gel, 30% and then 40% ethyl acetate in benzene) gave the title compound of Example 9 (4.8 g), a compound of the invention.

1H NMR (CDC13) # 7.7 (d,1H), 7.6-7.4 (m,5H), 7.25 (m,1H), 6.9 (dd,lH), 6.75 (s,lH), 3.80 (s,3H), 3.34 (s,3H).

EXAMPLE 10 Preparation of r3-r5-r2-(1 ,5-dihvdro-3-methoxv-1 -methvl-5-oxo-4H- 1,24-triazol-4- yl)phenoxyl- 1 ,2,44hiadiazol-3-yllphenyll trifluoromethanesulfonate To a solution of the title compound of Example 9 (0.2 g, 0.5 mmol) in methylene chloride (2.5 mL) was added pyridine (0.061 mL), trifluoromethanesulfonic anhydride (0.102 mL) and a catalytic amount of 4-(dimethylamino)pyridine. The reaction mixture

was stirred for 3 days before being diluted with methylene chloride and washed with HCI (1 N aqueous solution). The organic layer was dried over magnesium sulfate.

Concentration yielded the title compound of Example 10, a compound of the invention, as an off white solid. 1R NMR (CDC13) 8.2 (d,1R), 8.1 (s,1H), 7.65-7.45 (m,SH), 7.35 (dd, 1H), 3.80 (s,3H), 3.37 (s,3H).

EXAMPLE 11 Step A: Preparation of 2-furancarboximidamide (See Tetr. Lett. (1990), 31, 1969). To a solution of trimethylaluminum (18 mL, 2 M in hexanes) in toluene (40 mL) at 0 °C was added ammonium chloride (1.926 g) in small portions. Upon complete addition, the cooling bath was removed and the mixture was stirred for a further 1.5 h. 2-furonitrile (3.15 mL, 36.0 mmol) was added and the mixture was heated at 85 °C overnight. The mixture was then cooled and poured onto a slurry of silica gel (600 g) in chloroform (300 mL). The mixture was stirred for 5 min, filtered and washed with methanol (800 mL). Concentration yielded the title compound of Step A (4.01 g). 1H NMR (Me2SO-d6) 6 9.6 (br s, 2H), 9.3 (br s, 2H), 8.2 (m,lH), 7.98 (m,lH), 6.88 (m,lH).

Step B: Preparation of 5-chloro-3-(2-furanyl) 1 ,2,4-thiadiazole To a solution of the title compound of Step A (4.01 g, 36 mmol) in water (89 mL) and methylene chloride (177 mL) was added benzyltriethylammonium chloride (675 mg) and perchloromethyl mercaptan (4.0 mL) and the mixture was cooled in an ice bath. A solution of sodium hydroxide (4.36 g) in water (89 mL) was then added such that the internal temperature did not exceed 10 °C. Upon complete addition, the cooling bath was removed and the mixture was stirred for 3 h. The layers were separated and the organic layer was dried over magnesium sulfate. Purification by column chromatography (petroleum ether and then 1-chlorobutane) gave the title compound of Step B. 1H NMR (CDC13) 8 7.6 (m,lH), 7.19 (m,lH), 6.57 (m,lH).

Step C: Preparation of 4- [2- [[3-(2-furanyl)- 1,2 ,4-thiadiazol-5-yl]oxy]phenyl]-2,4- dihydro-5-methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one To a solution of the title compound of Step D in Example 1 (355 mg, 1.61 mmol) in acetone (3 mL) was added potassium carbonate (289 mg) and the title compound of Step B. The mixture was stirred overnight at ambient temperature before being diluted with water. The resulting mixture was extracted with methylene chloride three times and the combined extracts were dried over magnesium sulfate. The solution was concentrated to a solid which was recrystallized from ethanol to give the title compound of Step C (213 mg), a compound of the invention, as a solid melting at

107-108 "C. 1H NMR (CDC13) 7.55 (m,3H), 7.49 (m,2H), 7.07 (m,lH), 6.5 (m,lH), 3.79 (s,3H), 3.38 (s,3H).

EXAMPLE 12 Preparation of 4-[2-[[3-(5-bromo-2-thienyl)-1,2,4-thiadiazol-5-yl]oxy]pheny l]-2,4- dihydro-5-methoxy-2-methyl-3H- 1,2 ,4-triazol-3 -one To a solution of 5-chloro-3-(2-thienyl)-1,2,4-thiadiazole (prepared from 2-thiophenecarbonitrile according to the procedure described in Step C in Example 2) (1.0 g, 4.94 mmol) in methylene chloride was added bromine (0.253 mL). After 1 h, the mixture was concentrated and redissolved in acetone (8 mL). The title compound of Step D in Example 1 (850 mg) and potassium carbonate (1.33 g) were added and the mixture was stirred overnight before being diluted with water and twice extracted with methylene chloride. The organic phases were combined, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography (silica gel, ethyl ether) to give the title compound of Example 12, a compound of the invention.

1H NMR (CDCl3) 6 7.65-7.55 (m,2H), 7.5-7.45 (m,3H), 7.04 (d,lH), 3.80 (s,3H), 3.38 (s,3H).

EXAMPLE 13 Step A: Preparation of 5-chloro-3-(2,5-dichloro-3-thienyl)-1,2,4-thiadiazole A solution of 5-chloro-3-(3-thienyl)-l,2,4-thiadiazole (prepared from 3- thiophenecarbonitrile according to the procedure described in Step C in Example 2) (2.0 g, 9.88 mmol) in sulfuryl chloride (10 mL) was stirred at ambient temperature for 1.5 h before being poured into water and extracted with ethyl ether. The ether layer was washed with a saturated aqueous solution of NaRCO3 and dried over magnesium sulfate.

Concentration yielded the title compound of Step A (1.87 g). 1H NMR (CDCl3) 87.45 (s,lH).

Step B: Preparation of 4-r2-TT3-(2,5-dichloro-3-thienvl)- 1,2,4-thiadiazol-5- yl]oxy]phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triaz ol-3-one To a solution of the title compound of Step D in Example 1 (1.83 g, 6.74 mmol) in acetone (13 mL) was added potassium carbonate (1.21 g) and the title compound of Step A. The mixture was stirred at ambient temperature for 30 h at which point extra potassium carbonate (0.6 g) was added. When the reaction was judged to be complete by TLC analysis, it was diluted with ethyl acetate, washed twice with water, with saturated aqueous NaCl and the combined aqueous layers were re-extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, concentrated and the residue was purified by crystallization from ethanol. The mother liquor was concentrated and purified by column chromatography (silica gel, 60% and then 80%

ethyl ether in petroleum ether) to give the title compound of Step B (2.5 g), a compound of the invention, as a solid melting at 144-147 °C. 1H NMR (CDCl3) 6 7.65 (d,lH), 7.6-7.5 (m,lH), 7.5-7.4 (m,2H), 7.37 (s,lH), 3.81 (s,3H), 3.39 (s,3H).

EXAMPLE 14 Step A: Preparation of 2,2-dimethylpropanimidic acid hydrochloride To a solution of trimethylacetonitrile (100 g, 1.203 mol) in ethyl ether (600 mL) is added absolute ethanol (74.1 mL). The solution is cooled to 0 °C and then is saturated with dry HCl gas. The reaction mixture is then left to stand at ambient temperature for 6 days after which time it is concentrated to give the title compound of Step A (54.37 g) as a white solid. 1H NMR (Me2SO-d6) 611.4 (br s, 2H), 4.4 (q,2H), 1.22 (s,9H), 1.05 (t,3H).

Step B: Preparation of 2,2-dimethylpropanimidamide hydrochloride To a solution of the title compound of Step A (54.37 g, 328.2 mmol) in methanol (20 mL) is added ammonia (65.7 mL, 7N solution in methanol). This mixture was stirred for 3 days before being concentrated to give the title compound of Step B (33.15 g) as an off white solid. 1H NMR (Me2SO-d6) 6 1.25 (s,9H).

Step C: Preparation of 5-chloro-3-( 11 -dimethylethyl)- 1 2,4-thiadiazole To a solution of the title compound of Step B (5.0 g, 36.61 mmol) in water (23 mL) and methylene chloride (45 mL) is added perchloromethyl mercaptan (4.0 mL, 36.61 mmol) and the mixture is cooled in an ice bath. With efficient stirring, a solution of sodium hydroxide (5.86 g ) in water (23 mL ) is then added dropwise such that the internal temperature does not exceed 10 "C. After the addition is complete, the cooling bath is removed and the reaction mixture is stirred for a further 1.5 h. The organic layer is then separated, dried over magnesium sulfate and concentrated. The yellow/brown tar is extracted with boiling hexane and the hot solution is filtered through a pad of silica gel.

The silica gel is washed with hexane and the solution is concentrated to a give the title compound of Step C (5.88 g) as a yellow oil which is used without further purification.

1H NMR (CDC13) 6 1.42 (s,9H).

Step D: Preparation of 4-[2-[[3-( 11 -dimethylethyl)- 1 ,2,4-thiadiazol-5- ylloxylphenyll -2,4-dihydro-5-methoxy-2-methyl-3H- 12 4-triazol-3-one To a solution of the title compound of Step D in Example 1 (500 mg, 2.26 mmol) in DMF (4.5 mL) is added freshly ground potassium carbonate (406 mg) and the title compound of Step C (399 mg). The mixture was stirred at ambient temperature for 2 days before being diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated. Purification by column chromatography (silica gel, 40%, then 60%, and then 80% ethyl ether in petroleum

ether) yields the title compound of Step D (0.19 g), a compound of invention, as an off white solid melting at 110-111 OC. 1H NMR (CDC13) 67.58 (d,lH), 7.50 (m,lH), 7.47 (m,1H), 7.44 (m,lH), 3.78 (s,3H), 3.40 (s,3H), 1.36 (s,9H).

EXAMPLE 15 Preparation of 4-[2-[(6-chloro-2-pyrazinyl)oxy]phenyl]-2,4-dihydro-5-methox y-2- methyl-3H- 1 ,2,4-triazol-3-one To a solution of the title compound of Step D in Example 1 (2.2 g, 10.0 mmol) in DMF (10 mL) was added sodium hydride (0.47g, 60% oil dispersion) in small portions.

The resulting slurry was stirred for 5 min and then 2,6-dichloropyrazine (1.5 g, 10.1 mmol) was added all at once. The reaction mixture was stirred for 16 h at 70-75 "C, and then the DMF was removed by vacuum distillation. The residue was partitioned between 125 mL of ethyl acetate and 50 mL of water. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give a brown solid which was triturated with diethyl ether to afford 1.65 g of the title compound of Example 15, a compound of invention, as a white solid melting at 135-137 "C. 1H NMR (CDCl3) 6 8.30 (m,2H), 7.50 (m,1H), 7.40 (m,3H), 3.81 (s,3H), 3.33 (s,3H).

EXAMPLE 16 Preparation of 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[6-[4-(trifluoromethyl) phenyl]-2- pyrazinyl]oxy]phenyl]-3H-1,2,4-triazol-3-one A slurry made up of the title compound of Example 15 (3.0g, 9.12 mmol) and palladium acetate (76 mg) in dimethoxyethane (18.5 mL) was stirred for 0.5 h. To this mixture was added a solution of 4-trifluoromethylbenzene boronic acid (2.5 g, 13.1 mmol, available from Lancaster Synthesis Inc.) and sodium carbonate (3.1 g) in 46 mL of water. The reaction mixture was stirred at 100 °C for 5 h. The dimethoxyethane was removed under reduced pressure and the resulting mixture was partitioned between 150 mL of ethyl acetate and 50 mL of water. The aqueous layer was extracted with 50 mL of ethyl acetate and the combined organic layers were filtered through CeliteB, dried over anhydrous potassium carbonate, and concentrated under reduced pressure to give a crude product. Flash column chromatography (gradient elution with 60-75% ethyl acetate in hexane) gave the title compound of Example 16, a compound of the invention, as a white solid (3.3 g) melting at 145-148 "C. 1H NMR (CDCl3) 68.79 (s,lH), 8.39 (s,lH), 7.98 (d,2H), 7.67 (d,2H), 7.51 (m,lH), 7.41 (m,3H), 3.65 (s,3H), 3.31 (s,3H).

EXAMPLE 17 Preparation of 4-[6-[2-( 1 ,5-dihydro-3-methoxy- 1 -methyl-5-oxo-4H- 1 .2,4-triazol-4- yl)phenoxyl-2-pyrazinyllbenzonitrilc To a solution of the title compound of Example 15 (333 mg, 1.0 mmol) and tetrakis(triphenylphosphine)palladium (60 mg) in nitrogen-purged tetrahydrofuran (2.8 mL) was added a solution of bromo(4-cyanophenyl)zinc (2.8 mL, 0.5M in tetrahydrofuran, available from Rieke Metals, Inc.). The resulting dark solution was stirred for 22 h at room temperature and an additional 1.5 mL of the organozinc reagent was then added to complete the reaction. After stirring for another 6 h, the reaction mixture was partitioned between 100 mL of ethyl acetate and 50 mL of diluted aqueous hydrochloric acid. The aqueous layer was extracted with 50 mL of ethyl acetate and the combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a crude product. Flash column chromatography (gradient elution with 50-70% ethyl acetate in hexane) gave the title compound of Example 17, a compound of invention, as a white solid (230 mg) melting at 195-199 "C. 1H NMR (CDCl3) 5 8.79 (s,lH), 8.40 (s,lH), 8.00 (d,2H), 7.72 (d,2H), 7.53 (m,lH), 7.41 (m,3H), 3.68 (s,3H), 3.30 (s,3H).

EXAMPLE 18 Step A: Preparation of 5-(4-chlorophenyl)- 1,3 ,4-thiadiazol-2-amine The title compound was prepared according to Zubets, I. V.; Boikov, Yu. A.; Viktorovskii, I. V.; V'yunov, K. A.; Chem. Het. Comp. 1148 (1986). Starting from 4-chlorobenzaldehyde thiosemicarbazone (8.6g, 50.1 mmol), the reaction afforded 6.3 g of the title compound of Step A as an off white solid. 1H NMR (Me2SO-d6) 57.82-7.54 (AA'BB', 4H), 7.48 (s, 2H). Elemental analysis: (Calculated) C: 44.97, H: 3.77, N: 19.66, S:15.00. (Found) C: 45.10, H: 3.92, N: 19.67, S: 14.65.

Step B: Preparation of 2-chloro-5-(4-chlorophenyl)- 13 4-thiadiazole The title compound was prepared according to Zubets, I. V.; Boikov, Yu. A.; Viktorovskii, I. V.; V'yunov, K. A.; Chem. Het. Comp. 1148 (1986). Starting from the title compound of Step A (0.6g, 3 mmol), the reaction afforded 0.4 g of a yellow oil which was used without further purification. 1H NMR (Me2SO-d6) 6 8.02-7.67 (AA'BB', 4H).

Step C: Preparation of 4- [2-[ [5-(4-chlorophenyl)- 1,3 ,4-thiadiazol-2- ylloxylphenyll -2,4-dihydro-5-methoxy-2 methyl-3H- 1,2 4-triazol-3-one The title compound of Step B (0.46 g, 2 mmol), the title compound of Step D in Example 1 (0.44 g, 2 mmol) and potassium carbonate (0.8 g, 5.8 mmol) were combined in 30 mL of 4-methyl-pentane-2-one. The mixture was heated at reflux temperature for

5 h and was then allowed to cool to ambient temperature. The solvent was removed under reduced pressure and the residue was partitioned between 50 mL of ethyl acetate and 50 mL of water. The aqueous layer was extracted with ethyl acetate (2x30 mL).

The combined organic layers were extracted with 1N sodium hydroxide (2x20 mL) and saturated aqueous NaCl (2x20 mL), respectively. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Preparative TLC (eluent: ethyl acetate/hexane=2/1) afforded the title compound of Step C, a compound of invention, as a white solid. 1H NMR (Me2SO-d6) 6 7.92-7.45 (m,8H), 3.79 (s,3H). 3.25 (s,3H).

EXAMPLE 19 Step A: Preparation of 4- [3-(trifluoromethyl)phenyll -2-thiazolamine To a stirring solution of 10 g of 3'-(trifluoromethyl)acetophenone in 100 mL of dichloromethane was added dropwise 8.5 g of bromine. The bromine color dissipated immediately during the dropwise addition. The reaction mixture was then concentrated under reduced pressure and the resulting oil was dissolved in 80 mL of ethanol. To this oil was added 4.0 g of thiourea and the resulting mixture was heated at reflux for 8 h.

Upon cooling, a solid precipitated. Approximately 100 mL of diethyl ether was added to enhance precipitation. The solid was collected and washed with diethyl ether followed by neutralization with excess aqueous sodium bicarbonate. The free base was extracted into ethyl acetate. The ethyl acetate solution was washed with water and saturated aqueous Nazi. The ethyl acetate solution was then dried over MgSO4 and concentrated under reduced pressure to give 11.5 g of the title compound of Step A as a white (yellow tinted) solid melting at 87-88 "C. 1H NMR (CDC13) 58.05 (s,1H), 7.95 (d,lH), 7.5 (m,2H), 6.8 (s,lH), 5.15 (br s,2H).

Step B: Preparation of 5-bromo-4-[3-(trifluoromethyl)phenyll-2-thiazolamine To a stirring solution of 8.5 g of the title compound of Step A in 100 mL of dichloromethane was added dropwise 6 g of bromine. The bromine color dissipated immediately during the dropwise addition. The reaction mixture was stirred for 10 minutes after the addition and then was concentrated under reduced pressure. The resulting residue was partitioned between 150 mL of ethyl acetate and 100 mL of saturated aqueous NaRCO3 and the mixture was stirred for 0.5 h. The organic layer was separated, washed with saturated aqueous NaCl, dried over MgSO4 and concentrated under reduced pressure to give an oil which soon crystallized. The solid was suspended in hexanes, then collected by filtration to give 10.5 g of the title compound of Step B as a white solid melting at 96-98 °C. IH NMR (CDC13) 58.15 (s,lH), 8.05 (d,lH), 7.65 (d,lH), 7.55 (t,lH), 5.75 (br s,2H).

Step C: Preparation of 5-bromo-2-chloro-4-r3-(trifluoromethyl!phenyllthiazole The title compound of Step B (3 g) was dissolved in 50 mL of acetonitrile and to this solution was added with stirring 2.5 g of copper(II) chloride followed by 2 mL of tert-butylnitrite (dropwise). Nitrogen evolution was evident and the reaction exothermically warmed to approximately 30 °C. The dark reaction mixture was stirred for 45 min and was then partitioned between 200 mL of ethyl acetate and 200 mL of distilled water. The organic layer was separated, washed with 1N aqueous HCI, water, and then saturated aqueous NaC1. The organic layer was dried over MgSO4 and then was concentrated under reduced pressure to give a dark oil/solid residue. The main component was isolated by flash chromatography on silica gel using 5-10% ethyl acetate in hexanes as eluant to give 2.4 g of the title compound of Step C as a red tinted solid melting at 52-55 °C. 1H NMR (CDCl3) 8.2 (s,lH), 8.15 (d,1H), 7.65 (d,lH), 7.6 (t,lH).

Step D: Preparation of 4-[2-[[5-bromo-4-[3-(trifluoromethyl)phenyl]-2- thiazolyl]oxy]phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2, 4-triazol- 3-one To a stirring solution of 2.2 g of the title compound of Step C in 50 mL of acetonitrile was added 1.4 g of the title compound of Step D in Example 1 and 1.8 g of potassium carbonate. The reaction mixture was heated at reflux for 14 h and then was allowed to cool. The reaction mixture was partitioned between 100 mL of ethyl acetate and 100 mL of distilled water. The organic layer was separated, washed with distilled water, dried over MgSO4, and then concentrated under reduced pressure to give a dark oil. The main component was isolated by flash chromatography on silica gel using 50% ethyl acetate in hexanes as eluant to give 2.1 g of the title compound of Step D, a compound of the invention, as a gum. 1H NMR (CDCl3) 8.2 (s,1H), 8.1 (d,lR), 7.6 (d,lH), 7.35-7.55 (m,5H), 3.84 (s,3H), 3.40 (s,3H).

EXAMPLE 20 Preparation of 2,4-dihydro-5-methoxy-2-methyl-4-[2- [[4- [3-(trifluoromethyl)phenyl-2- thiazolylloxylphenyll-3H- 1,2 ,4-triazol-3-one A mixture of 0.8 g of the title compound of Step D in Example 19, 2.0 g of ammonium formate and 0.3 g of 10% palladium on carbon in 20 mL methanol was stirred at room temperature for 2 days. The reaction mixture was then filtered through CeliteR rinsing thoroughly with ethyl acetate. The filtrate was partitioned between 100 mL of ethyl acetate and 50 mL of distilled water. The organic layer was separated, washed with distilled water and then with saturated aqueous Nail. The organic layer was dried over MgS04 and then was concentrated under reduced pressure to give an oil.

The main component was isolated by flash chromatography on silica gel using 50% ethyl acetate in hexanes as eluant to give a white foam which crystallized to a white solid upon the addition of a small amount of diethyl ether. The solid was filtered to give 0.52 g of the title compound of Example 20, a compound of the invention, as a white solid melting at 116-118 °C. 1H NMR (CDC13) 6 8.05 (s,lH), 7.95 (d,1H), 7.35-7.6 (m,6H), 7.1 (s,lH), 3.81 (s,3H), 3.37 (s,3H).

EXAMPLE 21 Preparation of 2\4-dihydro-5-methoxy-2-methyl-4-l 2- l 1 5-methyl-4- [3- (trifluoromethyl)phenyl]-2-thiazolyl]oxy]phenyl]-3H-1,2,4-tr iazol-3-one To a stirring solution of 0.75 g of the title compound of Example 19 in Step D in 7 mL of tetrahydrofuran at -78 °C under N2 was added dropwise 0.70 mL of n-butyllithium (2.5 M in hexanes). The reaction was allowed to stir at -78 °C for 0.5 h, and then 0.12 mL of iodomethane was slowly added. After stirring at -78 °C for another 2 min, the cooling bath was removed and the reaction mixture was stirred an additional 2 h at ambient temperature. The reaction mixture was diluted with diethyl ether and washed with distilled water and saturated aqueous NaCl. The organic layer was dried over MgS04 and then was concentrated under reduced pressure. Purification by flash chromatography on silica gel using 50-60% ethyl acetate in hexanes as eluant gave 0.40 g of the title compound of Example 21, a compound of the invention, as an oil.

1H NMR (CDC13) 6 7.85 (s,lH), 7.8 (d,lH), 7.3-7.6 (m,6H), 3.85 (s,3H), 3.40 (s,3H), 2.49 (s,3H).

EXAMPLE 22 Step A: Preparation of N-(2-methoxy-6-methylphenyl)-2,2- dimethylhydrazinecarboxamide To a stirred solution of phosgene (108 g, 1.09 moles) in ethyl acetate (750 mL) at 0 °C was added dropwise 2-methoxy-6-methylaniline (125.0 g, 911 mmol) dissolved in ethyl acetate (250 mL) over 20 min. The reaction mixture was slowly warmed to room temperature and was then heated at reflux for 1 h. The solution was cooled to room temperature and was concentrated under reduced pressure to provide the crude isocyanate as a dark red liquid which was redissolved in ethyl acetate (1 L) and cooled to 0 °C. 1,1-Dimethylhydrazine (55.0 g, 911 mmol) was added dropwise over 30 min and then the mixture was allowed to warm to room temperature and stir overnight. The mixture was cooled, filtered, and the solid was washed with ethyl acetate and dried to provide 200.0 g of the title compound of Step A as a white solid melting at 151-153 °C.

1H NMR (CDCl3) 87.58 (br s,1R), 7.10 (t,lH), 6.84 (d,1H), 6.74 (d,lR), 5.22 (br s,lH), 3.80 (s,3H), 2.63 (s,6H), 2.31 (s,3H).

Step B: Preparation of 5-chloro-2,4-dihydro-4-(2-methoxy-6-methylphenyl)-2- methyl-3H- 1 ,2,4-triazol-3-one The title compound of Step A (100.0 g, 447.9 mmol) was suspended in ethyl acetate (1 L) and added dropwise, via mechanical pump, over 3.5 h to a stirring solution of phosgene (177 g, 1.79 moles) in ethyl acetate (1.5 L) which was heated at reflux.

After the addition was complete, the mixture was heated at reflux for a further 3 h, cooled to room temperature and stirred overnight. The solution was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and water and extracted four times with ethyl acetate. The combined organic phases were washed with saturated aqueous NaCl, dried (MgS04), filtered and concentrated to afford 111.4 g of the title compound of Step B as a pale yellow solid melting at 132-134 °C. H NMR (CDC13) 67.34 (t,lH), 6.93 (d,lR), 6.85 (d,lR), 3.79 (s,3H), 3.54 (s,3H), 2.20 (s,3H).

Step C: Preparation of 5-chloro-2,4-dihydro-4-(2-hydroxy-6-methylphenyl)-2- methyl-3H-1,2,4-triazol-3-one To a stirring solution of the title compound of Step B (15.0 g, 59.3 mmol) in benzene (200 mL) at 0 °C was added aluminum chloride (23.7 g, 178 mmol) in small portions. The mixture was warmed to room temperature and stirred for 2 days. The mixture was poured over ice and water and then extracted four times with ethyl acetate.

The combined organic phases were washed with saturated aqueous Nail, dried (MgSO4), filtered and concentrated to an oil that was purified by flash column chromatography on silica gel to provide 13.6 g of the title compound of Step C as a pale orange solid melting at 175-178 °C. 1H NMR (CDC13) 68.11 (s,lH), 6.92 (t,lH), 6.71 (d,lH), 6.41 (d,lH), 3.56 (s,3H), 2.12 (s,3H).

Step D: Preparation of 2,4-dihydro-4-(2-hydroxy-6-methylphenyl)-5-methoxy-2- methyl-3H- 1 ,2,4-triazol-3-one To a stirred solution of the title compound of Step C (133.5 g, 557.0 mmol) in tetrahydrofuran (1.5 L) was added dropwise sodium methoxide (25% by weight in methanol, 382 mL, 1.67 moles). The mixture was heated at reflux for 3 h, cooled to room temperature and then diluted with aqueous ammonium chloride and ethyl acetate.

The aqueous layer was acidified (pH 4-5) with 1N HCl and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous NaCI, dried (MgSO4), filtered and concentrated to a dark brown solid which was triturated with ethyl acetate to afford 75.0 g of the title compound of Step D as a white solid melting at 194-196 °C. 1H NMR (Me2SO-d6) 6 9.91 (s,lH), 7.17 (t,lH), 6.78 (m,2H), 3.84 (s,3H), 3.30 (s,3H), 2.03 (s,3H).

Step E: Preparation of 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-thiadiazol- S-ylloxyl-6-methylphenyll-2,4-dihydro-5-methoxy-2-methyl-3H- 1,2,4- triazol-3-one To a solution of 5-chloro-3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-thiadiazol e (1.50 g, 4.51 mmol, available from Maybridge, Catalog No. RDR03892) in DMF (10 mL) was added the title compound of Step D (1.06 g, 4.51 mmol) at room temperature. Potassium carbonate (1.25 g, 9.02 mmol) was added and the mixture was stirred for 18 h. The mixture was diluted with water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography on silica gel to provide 2.20 g of the title compound of Step E, a compound of the invention, as a white solid melting at 95-98 "C. 1H NMR (CDCl3) 5 8.64 (s,2H), 7.95(s,1R), 7.50 (t,lH), 7.42 (d,lH), 7.37 (d,lH), 3.80 (s,3H), 3.39 (s,3H), 2.33 (s,3H).

EXAMPLE 23 Step A: Preparation of 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[tris(1- methylethyl)silyl]oxy]phenyl]-3H-1,2,4-triazol-3-one To a solution of the title compound of Step D in Example 1 (10.54 g, 47.65 mmol) and imidazole (6.50 g, 95.3 mmol) in DMF (100 mL) was added dropwise triisopropylsilyl chloride (13.3 mL, 61.9 mmol) at 0 "C. The mixture was allowed to warm to room temperature and was stirred for 3 h. Then mixture was then diluted with aqueous sodium bicarbonate and water and was extracted three times with ethyl acetate.

The combined organic phases were washed with saturated aqueous Nail, dried (MgSO4), filtered and concentrated to an oil which was purified by flash column chromatography on silica gel to give 16.8 g of the title compound of Step A as a light tan solid melting at 107-109 °C. 1H NMR (CDC13) 6 7.27 (m,2H), 6.98 (m,2H), 3.89 (s,3H), 3.42 (s,3H), 1.25 (m,3H), 1.04 (m,18H).

Step B: Preparation of 4-[2-ethyl-6-[[tris(1-methylethyl)silyl]oxy]phenyl]-2 -2,4- dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one A solution of the title compound of Step A (2.16 g, 5.72 mmol) in anhydrous tetrahydrofuran was cooled to -78 °C and tert-butyllithium (4.0 mL, 1.7 M solution in pentane, 6.8 mmol) was added dropwise. The resulting dark yellow solution was stirred for 1 h at -78 °C and ethyl iodide (4.6 mL, 57.2 mmol) was then added dropwise and the mixture was slowly warmed to 0 °C and stirred for 20 min. The mixture was diluted with aqueous ammonium chloride and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous NaCl, dried (MgSO4),

filtered and concentrated. The crude product was purified by flash column chromatography on silica gel to afford 1.64 g of the title compound of Step B as a white solid melting at 90-92 °C. 1H NMR (CDC13) 6 7.23 (t,lH), 6.90 (d,lH), 6.77 (d,lR), 3.89 (s,3H), 3.43 (s,3H), 2.53 (q,2H), 1.24 (m, 3H), 1.15 (t,3H), 1.04 (m,18H).

Step C: Preparation of 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]- 1,2,4-thiadiazol- 5-ylloxyl-6-ethylphenyll-2.4-dihydro-S-methoxy-2-methyl-3H- 1,24- triazol-3-one The title compound of Step B (0.244 g, 0.60 mmol) and 5-chloro-3-[3,5- bis(trifluoromethyl)phenyl]-1,2,4-thiadiazole (0.200 g, 0.60 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL). A solution of tetrabutylammonium fluoride (0.70 mL, 1 .OM solution in tetrahydrofuran, 0.70 mmol) was added dropwise and the solution was stirred for 1 h at room temperature. The mixture was diluted with water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous NaC1, dried (MgS04), filtered and concentrated. The residue was purified by flash column chromatography on silica gel to afford 0.32 g of the title compound of Step C, a compound of the invention, as a white solid melting at 136-138 °C. 1H NMR (CDCl3) 5 8.64 (s,2H), 7.94 (s,lH), 7.56 (t, 1H), 7.42 (m, 2H), 3.80 (s,3H), 3.40 (s,3H), 2.63 (m,2H), 1.23 (t,3H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 14 can be prepared. The following abbreviations are used in the Tables which follow: t = tertiary, Me = methyl, Et = ethyl, Bu = butyl, Ph = phenyl, MeO = methoxy, EtO = ethoxy, CN = cyano, and NO2 = nitro.

TABLE 1 Compounds of Formula IA defined as: R9 R9 R9 R9 2-Br-Ph 2-Me-Ph 2-Et-Ph 4-EtO-2-pyrimidinyl 2-CN-Ph 2-F-Ph 2-CI-Ph 4,6-diMeO-2-pyrimidinyl 2,4-diC1-Ph 2-Me-4-CI-Ph 6-CF3-2-pyridinyl 4,6-diMe-2-pyrimidinyl 2-CF3-Ph 3,5-diCl-Ph 2-pyrimidinyl 6-CF3-4-pyrimidinyl 2-I-Ph 3,5-diCF3-Ph 4-pyrimidinyl 4-CF3-2-pyridinyl 4-NO2-Ph 2-MeO-Ph 4-MeO-2-pyrimidinyl 4-CF3-2-pyrimidinyl 4-CF30-Ph 2,6-diMeO-Ph 4-Me-2-pyrimidinyl 5-CF3-3-pyridinyl 4-Me-Ph 3-CF30-Ph 6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl 4-CI-Ph 4-Br-Ph S-Me-2-furanyl 5-CN-2-pyridinyl 3-Me-Ph 3-Et-Ph 2,5-diMe-3-thienyl 6-Me-2-pyridinyl 3-CF3-Ph 4-MeO-Ph 3-OCF2H-Ph 3,5-diBr-Ph 3-Cl-2-Me-Ph 4-t-Bu-Ph 4-OCF2H-Ph 4-t-Bu-2-pyridinyl 3-t-Bu-Ph 4-CN-Ph 3-Me3Si-Ph 4-Me3Si-2-pyridinyl 3-F-Ph 4-NO2-Ph 4-Me3Si-Ph 4-Me3Ge-2-pyridinyl 4-CF3-Ph 3 ,4-diMe-Ph 3-Me3Ge-Ph 4,6-diCF3-2-pyrimidinyl 3,4-diCl-Ph 3,5-diMe-Ph 4-Me3Ge-Ph 5-CF3-2-furanyl 3,4-diCF3-Ph 4-F-3-CF3-Ph 3-EtO-Ph 5-CF3-2-thienyl 4-F-Ph 5-F-3-CF3-Ph Ph (2-CN-Ph)CH2 3-Cl-Ph | 3-Br-Ph | 3-I-Ph | 4-I-Ph t-Bu TABLE 2 Compounds of Formula IA defined as: R9 R9 R9 3,4-diF-Ph | 4-Ph-Ph | 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl S-Me-2-furanyl C(CH3)3 | 2,5-diCl-3-thienyl | 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF3O-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph S-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C=C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-C02-t-Bu-Ph 2-Et-Ph | 4,6-diMeO-2-pyrimidinyl | 3-CO2Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl TABLE 3 Compounds of Formula IA defined as: R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3 -2-pyridi nyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph | 5-F-2-thienyl | 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph | 5-Cl-2-thienyl | 6-MeO-4-pyrimidinyl 3-CI-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3) | 2,5-diCl-3-thienyl | 2,5-diMe-3-thienyl 3-Br-Ph | 2,5-diBr-3-thienyl | 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3 Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph | 2,6-diMeO-Ph | 4-CO2Me-Ph 4-CI-Ph 3-CF30-Ph 4-C02-t-Bu-Ph 3-Me-Ph | 4-Br-Ph | 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph | 4MeO-Ph | 4CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridynyl 4-F-Ph | 4-F-3-CF3-Ph | 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5CF3-2-thienyl 3-(C#C)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH20-5-pyridinyl 4-OS02CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-CO2Et-Ph 2-CI-Ph 4,6-diMe-2-pyrimidinyl TABLE 4 Compounds of Formula IA defined as: R9 R9 R9 R9 2-Br-Ph 2-Me-Ph 2-Et-Ph 4-EtO-2-pyrimidinyl 2-CN-Ph 2-F-Ph 2-Cl-Ph 4,6-diMeO-2-pyrimidinyl 2,4-diCl-Ph 2-Me-4-Cl-Ph 6-CF3-2-pyridinyl 4,6-diMe-2-pyri midinyl 2-CF3-Ph 3,5-diCl-Ph 2-pyrimidinyl 6-CF3-4-pyrimidinyl 2-I-Ph 3,5-diCF3-Ph 4-pyrimidinyl 4-CF3-2-pyridinyl 4-NO2-Ph | 2-MeO-Ph | 4-MeO-2-pyrimidinyl | 4-CF3-2-pyrimidinyl 4-CF30-Ph 2,6-diMeO-Ph 4-Me-2-pyrimidinyl 5-CF3-3-pyridinyl 4-Me-Ph 3-CF30-Ph 6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl 4-CI-Ph 4-Br-Ph S-Me-2-furanyl 5-CN-2-pyridinyl 3-Me-Ph 3-Et-Ph 2,5-diMe-3-thienyl 6-Me-2-pyridinyl 3-CF3-Ph 4-MeO-Ph 3-OCF2H-Ph 3,5-diBr-Ph 3-Cl-2-Me-Ph 4-t-Bu-Ph 4-OCF2H-Ph 4-t-Bu-2-pyridinyl 3-t-Bu-Ph 4-CN-Ph 3-Me3Si-Ph 4-Me3Si-2-pyridinyi 3-F-Ph 4-N02-Ph 4-Me3Si-Ph 4-Me3Ge-2-pyridinyl 4-CF3-Ph 3,4-diMe-Ph 3-Me3Ge-Ph 4,6-diCF3-2-pyrimidinyl 3,4-diCl-Ph | 3,5-diMe-Ph | 4-Me3Ge-Ph | 5-CF3-2-furanyl 3,4-diCF3-Ph 4-F-3-CF3-Ph 3-EtO-Ph 5-CF3-2-thienyl 4-F-Ph 5-F-3-CF3-Ph Ph (2-CN-Ph)CH2 3-Cl-Ph | 3-Br-Ph | 3-I-Ph | 4-I-Ph t-Bu TABLE 5 Compounds of Formula IA defined as: R9 R9 R9 R9 2-Br-Ph 2-Me-Ph 2-Et-Ph 4-EtO-2-pyrimidinyl 2-CN-Ph 2-F-Ph 2-CI-Ph 4,6-diMeO-2-pyrimidinyl 2,4-diCl-Ph | 2-Me-4-Cl-Ph | 6-CF3-2-pyridinyl | 4,6-diMe-2-pyrimidinyl 2-CF3-Ph 3,5-diCl-Ph 2-pyrimidinyl 6-CF3-4-pyrimidinyl 2-I-Ph 3,5-diCF3-Ph 4-pyrimidinyl 4-CF3-2-pyridinyl 4-NO2-Ph 2-MeO-Ph 4-MeO-2-pyrimidinyl 4-CF3-2-pyrimidi nyl 4-CF30-Ph 2,6-diMeO-Ph 4-Me-2-pyrimidinyl 5-CF3-3-pyridi nyl 4-Me-Ph 3-CF30-Ph 6-MeO-4-pyrimidinyl 3-MeO-2-pyridi nyl 4-Cl-Ph 4-Br-Ph 5-Me-2-furanyl 5-CN-2-pyridinyl 3-Me-Ph 3-Et-Ph 2,5-diMe-3-thienyl 6-Me-2-pyridinyl 3-CF3-Ph 4-MeO-Ph 3-OCF2H-Ph 3,5-diBr-Ph 3-Cl-2-Me-Ph 4-t-Bu-Ph 4-OCF2H-Ph 4-t-Bu-2-pyridinyl 3-t-Bu-Ph 4-CN-Ph 3-Me3Si-Ph 4-Me3Si-2-pyridinyl 3-F-Ph 4-N02-Ph 4-Me3Si-Ph 4-Me3Ge-2-pyridi nyl 4-CF3-Ph 3,4-diMe-Ph 3-Me3Ge-Ph 4,6-diCF3-2-pyrimidi nyl 3,4-diCl-Ph 3,5-diMe-Ph 4-Me3Ge-Ph 5-CF3-2-furanyl 3,4-diCF3-Ph 4-F-3-CF3-Ph 3-EtO-Ph 5-CF3-2-thienyl 4-F-Ph 5-F-3-CF3-Ph Ph (2-CN-Ph)CH2 3-Cl-Ph 3-Br-Ph 3-I-Ph 4-I-Ph t-Bu TABLE 6 Compounds of Formula IA defined as: R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph | 4-Br-3Me-Ph | 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph | 2,5-diBr-3-thienyl | 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph | 2,6-diMeO-Ph | 4-CO2Me-Ph 4-CI-Ph 3-CF30-Ph 4-C02-t-Bu-Ph 3-Me-Ph | 4-Br-Ph | 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph | 4-CN-Ph | 5-CF3-3-pyridinyl 4-CF3-Ph 4-N02-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH20-5-pyridinyl 4-OS02CF3-Ph 3-C02Me-Ph 4-Cl-benzyl | 4-EtO-2-pyrimidinyl | 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-C02Et-Ph 2-Cl-Ph | 4,6-diMe-2-pyrimidinyl TABLE 7 Compounds of Formula IA defined as: R9 R9 R9 R9 2-Br-Ph 2-Me-Ph 2-Et-Ph 4-EtO-2-pyrimidinyl 2-CN-Ph 2-F-Ph 2-Cl-Ph 4,6-diMeO-2-pyrimidinyl 2,4-diCl-Ph | 2-Me-4-Cl-Ph | 6-CF3-2-pyridinyl | 4,6-diMe-2-pyrimidinyl 2-CF3-Ph 3,5-diCl-Ph 2-pyrimidinyl 6-CF3-4-pyrimidinyl 2-I-Ph 3,5-diCF3-Ph 4-pyrimidinyl 4-CF3-2-pyridinyl 4-N02-Ph 2-MeO-Ph 4-MeO-2-pyrimidinyl 4-CF3-2-pyrimidinyl 4-CF30-Ph 2,6-diMeO-Ph 4-Me-2-pyrimidinyl 5-CF3-3-pyridinyl 4-Me-Ph 3-CF30-Ph 6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl 4-Cl-Ph 4-Br-Ph 5-Me-2-furanyl 5-CN-2-pyridinyl 3-Me-Ph 3-Et-Ph 2,5-diMe-3-thienyl 6-Me-2-pyridinyl 3-CF3-Ph 4-MeO-Ph 3-OCF2H-Ph 3,5-diBr-Ph 3-Cl-2-Me-Ph 4-t-Bu-Ph 4-OCF2H-Ph 4-t-Bu-2-pyridinyl 3-t-Bu-Ph 4-CN-Ph 3-Me3Si-Ph 4-Me3Si-2-pyridinyl 3-F-Ph 4-N02-Ph 4-Me3Si-Ph 4-Me3Ge-2-pyridinyl 4-CF3-Ph 3,4-diMe-Ph 3-Me3Ge-Ph 4,6-diCF3-2-pyrimidinyl 3,4-diCl-Ph | 3,5-diMe-Ph | 4-Me3Ge-Ph | 5-CF3-2-furanyl 3 ,4-diCF3-Ph 4-F-3-CF3-Ph 3-EtO-Ph 5-CF3-2-thienyl 4-F-Ph 5-F-3-CF3-Ph Ph (2-CN-Ph)CH2 3-Cl-Ph | 3-Br-Ph | 3-I-Ph | 4-I-Ph t-Bu TABLE 8 Compounds of Formula IA defined as: R9 R9 R9 R9 2-Br-Ph 2-Me-Ph 2-Et-Ph 4-EtO-2-pyrimidinyl 2-CN-Ph 2-F-Ph 2-CI-Ph 4,6-diMeO-2-pyrimidinyl 2,4-diCl-Ph 2-Me-4-Cl-Ph 6-CF3-2-pyridinyl 4,6-diMe-2-pyrimidinyl 2-CF3-Ph 3,5-diCl-Ph 2-pyrimidinyl 6-CF3-4-pyrimidinyl 2-I-Ph 3,5-diCF3-Ph 4-pyrimidinyl 4-CF3-2-pyridinyl 4-NO2-Ph 2-MeO-Ph 4-MeO-2-pyrimidinyl 4-CF3-2-pyrimidinyl 4-CF30-Ph 2,6-diMeO-Ph 4-Me-2-pyrimidinyl 5-CF3-3-pyridinyl 4-Me-Ph 3-CF30-Ph 6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl 4-Cl-Ph | 4-Br-Ph | 5-Me-2-furanyl | 5-CN-2-pyridinyl 3-Me-Ph 3-Et-Ph 2,5-diMe-3-thienyl 6-Me-2-pyridinyl 3-CF3-Ph 4-MeO-Ph 3-OCF2H-Ph 3,5-diBr-Ph 3-Cl-2-Me-Ph 4-t-Bu-Ph 4-OCF2H-Ph 4-t-Bu-2-pyridinyl 3-t-Bu-Ph 4-CN-Ph 3-Me3Si-Ph 4-Me3Si-2-pyridinyl 3-F-Ph 4-N02-Ph 4-Me3Si-Ph 4-Me3Ge-2-pyridinyl 4-CF3-Ph 3,4-diMe-Ph 3-Me3Ge-Ph 4,6-diCF3-2-pyn'rnidinyl 3,4-diCl-Ph | 3,5-diMe-Ph | 4-Me3Ge-Ph | 5-CF3-2-furanyl 3,4-diCF3-Ph 4-F-3-CF3-Ph 3-EtO-Ph 5-CF3-2-thienyl 4-F-Ph 5-F-3-CF3-Ph Ph (2-CN-Ph)CH2 3-Cl-Ph 3-Br-Ph 3-I-Ph 4-I-Ph t-Bu TABLE 9 R9 R9 R9 3 ,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph | 4-Br-3-Me-Ph | 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-C02Me-Ph 4-Cl-Ph | 3-CF3O-Ph | 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-C02Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyri mid ny I 3-Cl-2-Me-Ph | 4-MeO-Ph | 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH20-5-pyridinyl 4-OS02CF3-Ph 3-C02Me-Ph 4-Cl-benzyl | 4-EtO-2-pyrimidinyl | 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-CO2Et-Pb 2-Cl-Ph 4,6-diMe-2-pyrimidinyl TABLE 10 Compounds of Formula IA defined as: RlOa = H and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph | 2,5-diF-3-thienyl | 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph | 2-F-Ph | 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph | 4-MeO-Ph | 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-C02-t-Bu-Pb 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-C02Et-Ph 2-CI-Ph 4,6-diMe-2-pyrimidinyl RlOa = Me and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph | 3-Br-4-MeO-Ph | 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph | 5-Br-2-thienyl | 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-CI-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 | 2,5-diCl-3-thienyl | 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph | 2,6-diMeO-Ph | 4-CO2Me-Ph 4-CI-Ph 3-CF30-Ph 4-C02-t-Bu-Ph 3-Me-Ph | 4-Br-Ph | 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-CI-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl | 2-Cl-benzyl | 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-CO2Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl RlOa = Br and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-CI-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2.5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph | 4-SCF2H-Ph | 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl | 3-Cl-benzyl | 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl | 2-CN-benzyl | 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-C02-t-Bu-Pb 2-Et-Ph | 4,6-diMeO-2-pyrimidinyl | 3-CO2Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl R10a = Cl and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph | 4-Br-3-Me-Ph | 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph | 5-Br-2-thienyl | 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph | 2,6-diMeO-Ph | 4-CO2Me-Ph 4-Cl-Ph 3-CF30-Ph 4-C02-t-Bu-Ph 3-Me-Ph | 4-Br-Ph | 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph | 4-MeO-Ph | 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-Benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-C02Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl R10a = CN and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph | 4-Br-3-Me-Ph | 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidi nyl 3,5-diF-Ph | 5-F-2-thienyl | 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph | 2,5-diBr-3-thienyl | 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-CO2Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl R10a= F and R10a= I and R10a= n-propyl amd R10a= isopropyl and R9 R9 R9 R9 3-CF3-Ph | 3-CF3-Ph | 3-CF3-Ph | 3-CF3-Ph 3-CF3O-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph C(CH3)3 C(CH3)3 C(CH3)3 C(CH3)3 RlOa = n-butyl and R1Oa = tert-butyl and RlOa = CF3 and RlOa = MeO and R9 R9 R9 R9 3-CF3-Ph 3-CF3-Ph 3-CF3-Ph 3-CF3-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-OCF2H-Ph | 3-OCF2H-Ph | 3-OCF2HPh | 3-OCF2H-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph C(CH3)3 C(CH3)3 C(CH3)3 C(CH3)3 TABLE 11 Compounds of Formula IA defined as: R9 R9 R9 3 ,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph | 4-Br-3-Me-Ph | 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pirimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph | 4-F-3-CF3-Ph | 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl | 2-Cl-benzyl | 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-CO2Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl TABLE 12 Compounds of Formula IA defined as: R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph | 4-Br-3-Me-Ph | 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyri midi nyl 3,5-diF-Ph | 5-F-2-thienyl | 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph | 5-Cl-2-thienyl | 6-MeO-4-pyrimidinyl 3-CI-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2MePh 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-CO2Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl TABLE 13 Compounds of Formula IA defined as: RlOa = H and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph | 4-Br-3-Me-Ph | 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph | 4-SCF2H-Ph | 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF3O-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF30-Ph 4-C02-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-N02-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl3-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-CO2Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl R10a= Me and R9 R9 R9 3,4-diF-Ph 4-Pb-Pb 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph | 4-Br-3-Me-Ph | 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph | 5-F-2-thienyl | 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph | 2,5-diBr-3-thienyl | 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph | 2-F-Ph | 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-l-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3 ,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph | 5-F-3-CF3-Ph | 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH20-5-pyridinyl 4-OS02CF3-Ph 3-C02Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-C02-t-Bu-Ph 2-Et-Ph | 4,6-diMeO-2-pyrimidinyl | 3-CO2Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl R10a = Br and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-CI-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCI-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph | 2-Me-4-Cl-Ph | 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph | 3,5-diCF3-Ph | Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-C02Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyì 4-CF3-Ph 4-N02-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidi nyl 3-CO2Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl RlOa = Cl and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Pb 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph | 4-t-Bu-Ph | 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-C02-t-Bu-Pb 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-CO2Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl RlOa = CN and R9 R9 R9 3,4-diF-Ph | 4-Ph-Ph | 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-CI-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3) 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph | 2-F-Ph | 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph | 3,5-diCl-Ph | 4-Me3Ge-Ph 4-N02-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN2-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5 -diBr-Pb 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-C02Et-Ph 2-CI-Ph 4,6-diMe-2-pyrimidinyl R10a = F and | R10a = I and | R10a = n-propyl and | R10a = isopropyl and R9 R9 R9 R9 3-CF3-Ph 3-CF3-Ph 3-CF3-Ph 3-CF3-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph C(CH3)3 C(CH3)3 C(CH3)3 C(CH3)3 RlOa = n-butyl and R10a = tert-butyl and RlOa = CF3 and RlOa = MeO and R9 R9 R9 R9 3-CF3-Ph 3-CF3-Ph 3-CF3 -Ph 3-CF3-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diCl-Ph | 3,5-diCl-Ph | 3,5-diCl-Ph | 3,5-diCl-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph C(CH3)3 C(CH3)3 C(CH3)3 C(CH3)3 TABLE 14 Compounds of Formula IA defined as: R10a = H and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-l-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph | 4-NO2-Ph | 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-DiMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl | 3-Cl-benzyl | 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-C02Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl R10a = Me and R9 R9 R9 3 ,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph | 4-Br-3-Me-Ph | 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph | 5-F-2-thienyl | 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph | 5-Cl-2-thienyl | 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph | 2,6-diMeO-Ph | 4-CO2Me-Ph 4-CI-Ph 3-CF30-Ph 4-C02-t-Bu-Ph 3-Me-Ph | 4-Br-Ph | 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl | 2-Cl-benzyl | 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C-CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-C02Et-Ph 2-CI-Ph 4,6-diMe-2-pyrimidinyl R10a = Br and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-CI-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-dibr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph | 2,6-diMeO-Ph | 4-CO2Me-Ph 4-CI-Ph 3-CF30-Ph 4-C02-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph | 4-NO2-Ph | 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph | 3,5-diMe-Ph | 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph | 5-F-3-CF3-Ph | 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyri midi ny I 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH20-5-pyridinyl 4-OS02CF3-Ph 3-C02Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-CO2Et-Ph 2-CI-Ph 4,6-diMe-2-pyrimidinyl R10a = Cl and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyri midinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph | 5-Br-2-thienyl | 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Ph 4-Cl-Ph 3-CF3O-Ph 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph | 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-N02-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph | 5-F-3-CF3-Ph | 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl | 2-Cl-benzyl | 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH2O-5-pyridinyl 4-OSO2CF3-Ph 3-CO2Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-C02Et-Ph 2-CI-Ph 4,6-diMe-2-pyrimidinyl R10a = CN and R9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridinyl 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 2-pyrimidinyl 3-Cl-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienyl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-CI-Ph 2,5-diF-3-thienyl 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCF2H-Ph 4-OCF2H-Ph 2-CN-Ph 2-Me-Ph 3-Me3Si-Ph 2,4-diCl-Ph 2-F-Ph 4-Me3Si-Ph 2-CF3-Ph 2-Me-4-Cl-Ph 3-Me3Ge-Ph 2-I-Ph 3,5-diCl-Ph 4-Me3Ge-Ph 4-NO2-Ph 3,5-diCF3-Ph Ph 4-CF30-Ph 2-MeO-Ph 3-CN-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CO2Me-Pb 4-Cl-Ph | 3-CF3O-Ph | 4-CO2-t-Bu-Ph 3-Me-Ph 4-Br-Ph 4-CO2Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-t-Bu-Ph 4-t-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl 4-CF3-Ph 4-NO2-Ph 3-MeO-2-pyridinyl 3,4-diCl-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-t-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-Cl-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C#C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-C#C)-Ph 5-CF3-2-thienyl 3-(C#CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C#CH)-Ph 3-OSO2CF3-Ph 4-I-Ph 2-CF3CH20-5-pyridinyl 4-OS02CF3-Ph 3-C02Me-Ph 4-Cl-benzyl | 4-EtO-pyrimidinyl | 3-CO2-t-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-CO2Et-Pb 2-Cl-Ph 4,6-diMe-2-pyrimidinyl R10a = F and R10a = I and R10a = n-propyl and R10a = isopropyl and R9 R9 R9 R9 3-CF3-Ph 3 -CF3 -Ph 3-CF3-Ph 3-CF3-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diF-Ph 3 ,5-diF-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph C(CH3)3 C(CH3)3 C(CH3)3 C(CH3)3 R10a = n-butyl and R1Oa = tert-butyl and RlOa = CF3 and RlOa = MeO and R9 R9 R9 R9 3-CF3-Ph | 3-CF3-Ph | 3-CF3-Ph | 3-CF3-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-CF30-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCl-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph 3,5-diCF3-Ph C(CH3)3 C(CH3)3 C(CH3)3 C(CH3)3 Formulation/Utility Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.

Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further

include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release of the active ingredient.

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 to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water-soluble 5-90 W94 1-15 Granules, Tablets and Powders.

Suspensions, Emulsions, Solutions 5-50 40-95 0-15 (including Emulsifiable Concentrates) Dusts 1-25 70-99 0-5 Granules and Pellets 0.01-99 5-99.99 0-15 High Strength Compositions 90-99 0-10 0-2 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 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 and the like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and

bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-bydroxy-4- methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 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 U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.

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 10-41; 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 prepared in conventional ways. Compound numbers refer to compounds in Index Tables A-M.

Example A Wettable Powder Compound 345 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.

Example B Granule Compound 515 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.

Example C Extruded Pellet Compound 680 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 699 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%.

The compounds of this invention are useful 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, or to the plant seed or seedling to be protected, an effective amount of a compound of the invention 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. 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, Pkytophthorn infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythiuni aphanidermatum, Alterna ria brassicae, Septoria nodorum, Septoria tritici, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Moniliniafructicola, 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, Scleroti7lia sclerotiorum,

Sclerotium rolfsii, Erysiphe polygoni, Pyrenophora teres, Gaeumannomyces graminis, Rynchosporium secalis, Fusarium roseum, Bremia lactucae and other generea and species closely related to these pathogens.

The compounds of this invention also exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding, stem or root feeding, seed-feeding, aquatic and soil-inhabiting arthropods (term "arthropods" includes insects, mites and nematodes) which are pests of growing and stored agronomic crops, forestry, greenhouse crops ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health. Those skilled in the art will appreciate that not all compounds are equally effective against all growth stages of all pests. Nevertheless, all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the Order Lepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order Coleoptera; eggs, immatures and adults of the Orders Hemiptera and Homoptera; eggs, larvae, nymphs and adults of the Order Acari; eggs, immatures and adults of the Orders Thysanoptera, Orthoptera and Dermaptera; eggs, immatures and adults of the Order Diptera; and eggs, juveniles and adults of the Phylum Nematoda. The compounds of this invention are also active against pests of the Orders Hymenoptera, Isoptera, Siphonaptera, Blattaria, Thysanura and Psocoptera; pests belonging to the Class Arachnida and Phylum Platyhelminthes.

Specifically, the compounds are active against southern corn rootworm (Diabrotica undecimpuncrnta howardi), aster leafhopper (Mascrosteles fascitrons), boll weevil (Anthonomus grandis), two-spotted spider mite (Tetranychus urticae), fall armyworm (Spodopterafrugiperda), black bean aphid (Aphis fabae), green peach aphid (Myzuls persica), cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis noMa) English grain aphid (Sitobion avenae), tobacco budworm (Heliothis virescens), rice water weevil (Lissorhoptrus oryzophilus), rice leaf beetle (Oulema oryzae), whitebacked planthopper (Sogatella furcifera), green leafhopper (Nephotettix cincticeps), brown planthopper (Nilaparvata lugens), small brown planthopper (Laodelphax striatellus), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), black rice stink bug (Scotinophara lurida), rice stink bug (Oebalus pugnax), rice bug (Leptocorisa chinensis), slender rice bug (Cletus puntiger), and southern green stink bug (Nezara viridula). The compounds are active on mites, demonstrating ovicidal, larvicidal and chemosterilant activity against such families as Tetranychidae including Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacific us, Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi, Panonychus citri, Eotetranychus carpini borealis, Eotetranychus, hicoriae, Eotetranychus sexmaculatus,

Eotetranychus yumensis, Eotetranychus banksi and Oligonychus p ra tens is; Tenuipalpidae including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpus obovatus; Eriophyidae including Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae. See WO 90/10623 and WO 92/00673 for more detailed pest descriptions.

Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, 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 such agricultural protectants with which compounds of this invention can be formulated are: insecticides such as abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, esfenvalerate, fenpropathrin, fenvalerate, fipronil, flucythrinate, tau-fluvalinate, fonophos, imidacloprid, isofenphos, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, rotenone, sulprofos, tebufenozide, tefluthrin, terbufos, tetrachlorvinphos, thiodicarb, tralomethrin, trichlorfon and triflumuron; fungicides such as azoxystrobin (ICIA5504), benomyl, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), bromuconazole, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper salts, cymoxanil, cyproconazole, cyprodinil (CGA 219417), diclomezine, dicloran, difenoconazole, dimethomorph, diniconazole, diniconazole-M, dodine, edifenphos, epoxyconazole (BAS 480F), fenarimol, fenbuconazole, fenpiclonil, fenpropidin, fenpropimorph, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, fural axyl, hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl (BAS 490F), mancozeb, maneb, mepronil, metalaxyl, metconazole, myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propiconazole, pyrifenox, pyroquilon, sulfur, tebuconazole, tetraconazole, thiabendazole, thiophanate-methyl, thiram, triadimefon, triadimenol, tricyclazole, triticonazole, uniconazole, validamycin and vinclozolin; nematocides such as aldoxycarb and fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and

tebufenpyrad; and biological agents such as Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.

In certain instances, combinations with other fungicides or arthropodicides having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management.

Preferred for better control of plant diseases caused by fungal plant pathogens (e.g., lower use rate or broader spectrum of plant pathogens controlled) or resistance management are mixtures of a compound of this invention with a fungicide selected from the group cyproconazole, cyprodinil (CGA 219417), epoxyconazole (BAS 480F), fenpropidin, fenpropimorph, flusilazole and tebuconazole. Specifically preferred mixtures (compound numbers refer to compounds in Index Tables A-M) are selected from the group: compound 290 and cyproconazole; compound 290 and cyprodinil (CGA 219417); compound 290 and epoxyconazole (BAS 480F); compound 290 and fenpropidin; compound 290 and fenpropimorph; compound 290 and flusilazole; compound 290 and tebuconazole; compound 295 and cyproconazole; compound 295 and cyprodinil (CGA 219417); compound 295 and epoxyconazole (BAS 480F); compound 295 and fenpropidin; compound 295 and fenpropimorph; compound 295 and flusilazole; compound 295 and tebuconazole; compound 343 and cyproconazole; compound 343 and cyprodinil (CGA 219417); compound 343 and epoxyconazole (BAS 480F); compound 343 and fenpropidin; compound 343 and fenpropimorph; compound 343 and flusilazole; compound 343 and tebuconazole; compound 345 and cyproconazole; compound 345 and cyprodinil (CGA 219417); compound 345 and epoxyconazole (BAS 480F); compound 345 and fenpropidin; compound 345 and fenpropimorph; compound 345 and flusilazole; compound 345 and tebuconazole; compound 358 and cyproconazole; compound 358 and cyprodinil (CGA 219417); compound 358 and epoxyconazole (BAS 480F); compound 358 and fenpropidin; compound 358 and fenpropimorph; compound 358 and flusilazole; compound 358 and tebuconazole; compound 507 and cyproconazole; compound 507 and cyprodinil (CGA 219417); compound 507 and epoxyconazole (BAS 480F); compound 507 and fenpropidin; compound 507 and fenpropimorph; compound 507 and flusilazole; compound 507 and tebuconazole; compound 515 and cyproconazole; compound 515 and cyprodinil (CGA 219417); compound 515 and epoxyconazole (BAS 480F); compound 515 and fenpropidin; compound 515 and fenpropimorph; compound 515 and flusilazole; compound 515 and tebuconazole; compound 538 and cyproconazole; compound 538 and cyprodinil (CGA 219417); compound 538 and epoxyconazole (BAS 480F); compound 538 and fenpropidin; compound 538 and fenpropimorph;

compound 538 and flusilazole; compound 538 and tebuconazole; compound 699 and cyproconazole; compound 699 and cyprodinil (CGA 219417); compound 699 and epoxyconazole (BAS 480F); compound 699 and fenpropidin; compound 699 and fenpropimorph; compound 699 and flusilazole; and compound 699 and tebuconazole.

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.

For plant disease control, 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 fi-om 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.

Arthropod pests are controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying one or more of the compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. Thus, the present invention further comprises a method for the control of foliar and soil inhabiting arthropods and nematode pests and protection of agronomic and/or nonagronomic crops, comprising applying one or more of the compounds of the invention, or compositions containing at least one such compound, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected. or directly on the pests to be controlled. A preferred method of application is by spraying.

Alternatively, granular formulations of these compounds can be applied to the plant foliage or the soil. Other methods of application include direct and residual sprays, aerial sprays, seed coats, microencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, dusts and many others. The compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like.

For the control arthropod pests, the compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. A preferred method of application involves spraying a water dispersion or refined oil solution of the compounds.

Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.

The rate of application required for effective control will depend on such factors as the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.001 kg/hectare may be sufficient or as much as 8 kg hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required.

The following TESTS demonstrate the control efficacy of compounds of this invention on specific pathogens and arthropod pests. For the tests on arthropod pests, "control efficacy" represents inhibition of arthropod development (including mortality) that causes significantly reduced feeding. The pathogen and arthropod pest control protection afforded by the compounds is not limited, however, to these species. See Index Tables A-M for compound descriptions. The following abbreviations are used in the Index Tables which follow: t = tertiary, n = normal, i = iso, c = cyclo, Me = methyl, Et = ethyl, Pr = propyl, i-Pr = isopropyl, Bu = butyl, Ph = phenyl, MeO and OMe = methoxy, EtO = ethoxy, PhO = phenoxy, MeS = methylthio, CHO = formyl, CN = cyano, CO2Me = methoxycarbonyl, CO2Et = ethoxycarbonyl, NO2 = nitro, Me3Si = trimethylsilyl, Et3Si = triethylsilyl, MeNH = methylamino, Me2N = dimethylamino, MeS(O) = methylsulfinyl, and MeSO2 and SO2Me = methylsulfonyl. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared.

INDEX TABLE A Cmpd No. Structure m. p. (°C) OCH3 140-142 CI,OCH3 Cl¼¼ 0 NN CH3 237 oil CH3 0N N N CH30 ( t O N-N CH2CH3 238 > oil* 0 cm3 ""N N CR3 MeO n°° 0 0-N Me 732 X 85-X8 CH3 X CH3 CH30 ( t O N-N CH2CH3 981 160-163 0 0, CH30,N CF3 NNH CF3 982 * CR3 CH30r N; N-NH CF3 NNH 3 983 a CH3 83-85 CH3, CH3(N<O )// N-N N\ CF3 CH3 984 CH3 t/%l/'CF3 166-168 ,o II N cH3M¼O N-N CH3 a Compound contains 33% by weight of 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3- (trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]-3-thien yl]-3H-1,2,4-triazol-3- one.

*See Index Table M for 1H NMR data.

INDEX TABLE B Cmpd No. Y Z m.p. (°C) 2 0 2-MeO-Ph oil 3 O CH2-Ph oil* 4 Me oil 5 CH2O 2-Me-Ph oil* 122 CH20N=C(Me) 3-CF3-Ph 59-61 123 CH2ON=C(Me) 4-CF3-Ph oil 124 CH20N=C(Me) Me 71 -73 125 CH20N=C(Me) 3-Cl-Ph oil 126 CH2ON=C(Me) 3-Br-Ph oil* 127 CH20N=C(Me) 4-Cl-Ph oil 128 CH2ON=C(Me) 4-Br-Ph oil* 129 CH20N=C(Me) 4-F-Ph oil* 130 CH20N=C(Me) 4-MeO-Ph oil* 131 CH2ON=C(Me) 3-CN-Ph oil* 132 CH20N=C(Me) 4-CN-Ph oil* 133 CH20N=C(Me) 4-Me-Ph oil* 134 CH2ON=C(Me) 4-Cl-3-Me-Ph oil* 135 CH20N=C(Me) 3,4-(-OCH20-)-Ph oil 136 CH2ON=C(Me) 3,4-diMe-Ph oil 137 CH2ON=C(Me) 3,4-diCl-Ph oil* 138 CH2ON=C(Me) 4-Ph-Ph oil 139 CH2ON=C(Me) 3-t-Bu-Ph oil; 140 CH20N=C(Me) 3,5-diCF3-Ph oil 141 CH20N=C(Me) 3-MeO-Ph oil* 142 CH20N=C(Me) 3-Ph-Ph oil 143 CH20N=C(Me) 4-PhO-Ph oil* 144 CH2ON=C(Me) 2-pyridinyl oil* 145 CH2ON=C(Me) 3-Me2N-Ph oil* 146 CH20N=C(Me) 3-CF30-Ph oil* 147 CH20N=C(Me) 4-(4-MeO-PhO)-Ph 148 CH20N=C(Me) 4-CF3-2-pyridinyl 94-90 149 CH20N=C(Me) 5-CI-2-thienyl 123-125 150 CH20N=C(Me) 4-Me-2-thienyl 130-132 151 CH2ON=C(Me) 2-thienyl 124-126 152 CH20N=C(Me) 3-thienyl 129-131 153 CH20N=C(Me) 3-PhO-Ph oil* 154 CH20N=C(Me) 3-i-PrO-Ph oil* 155 CH20N=C(Me) 3,5-diCl-Ph oil* 156 CH20N=C(Et) 3-CF3-Ph oil* 157 CH20N=C(Me) c-hexyl oil* 158 CH20N=C(Me) 4-t-Bu-c-hexyl oil* 159 CH2ON=C(Me) 3-(3-CF3-Ph)-Ph oil* 160 CH2ON=C(Me) 3-(3-CF3-PhO)-Ph oil* 161 CH20N=C(Me) 3-F-5-CF3-Ph oil 162 CH20N=C(Me) 3,5-diMe-Ph oil* 163 CH20N=C(Me) 2-benzofuranyl 101-104 164 CH2ON=C(Me) 5-Me-2-furanyl oil* 165 CH2ON=C(Me) 4.6-diMe-2-pyridi nyl oil* 166 CH2ON=C(Me) 4-c-hexyl-Ph oil* 167 CH2ON=C(Me) 2-quinolinyl 134-136 168 CH2ON=C(Me) 4-Me-2-Ph-5-pyrimidinyl oil* 169 CH20N=C(Me) benzo[b]thiophen-3-yl oil* 170 CH20N=C(Me) 5-(3-CF3-Ph)-2-thienyl 135-138 171 CH2ON=C(Me) 3,5-diBr-Ph oil* 172 CH20N=C(Me) 4-F-3-CF3-Ph oil* 173 CH20N=C(Me) 2-Cl-6-MeO-4-pyridinyl oil* 174 CH20N=C(Me) 4,5-diMe-2-thiazolyl 76-78 175 CH20N=C(Me) I-Me-3-indolyl 114-116 176 CH2ON=C(OMe) 3,5-diCl-Ph oil* 177 CH20N=C(Me) 3-Et-Ph oil 178 CH20N=C(Me) 6-MeO-2-pyrimidinyl oil' 179 CH2ON=C(Me) 2-naphthalenyl oil* 180 CH20N=C(Me) 6-Me-2-naphthalenyl oil* 181 CH2ON=C(Me) 6-MeO-2-naphthalenyl oil* 182 CH20N=C(Me) 6-Br-2-naphthalenyl oil* 183 CH20N=C(Me) 5,6,7,8-tetrahydro-2-naphthalenyl oil* 239 0 3-[3,5-bis(trifluoromethyl)- 94-97 phenyl]-1,2,4-thiadiazol-5-yl 240 OCH2 4-MeO-Ph solid *See Index Table M for H NMR data.

INDEX TABLE C Cmpd W X Y Z m.p. (°C) 6 0 MeS O Ph 129-130 7 0 MeO O Me 123-126 8 0 MeO Me 95-97 9 0 MeS Me 95-97 10 0 Cl Me 99-100 11 O MeO O Ph 88-91 12 O Cl CH2O 2-Me-Ph 88-96 13 O MeO CH2O 2-Me-Ph 110-113 14 O EtO CH2O 2-Me-Ph oil* 15 0 MeS CH20 2-Me-Ph 80-88 16 O OCH2C#CH CH2O 2-Me-Ph 122-130 17 O Cl CH2ON=C(Me) 4-Me-Ph oil* 18 0 MeO CH20N=C(Me) 4-Me-Ph 116-118 19 0 MeS CH20N=C(Me) 4-Me-Ph oil 20 0 Cl CH2ONv oil 21 S MeS O Ph oil* 22 0 MeO CR2CHN 126-130 23 0 Cl CH2ON=C(H) Ph oil' 24 0 MeS CR2CHN oil 25 O Cl CH2O 3-(PhO)-Ph oil 26 0 MeO CH2O 3-(PhO)-Ph 27 O MeO CH2ON=C(H) Ph 101-104 28 0 MeS CH2O 3-(PhO)-Ph 95-100 29 0 Cl CH2S 2-Me-Ph 106-109 30 0 MeO CH2S 2-Me-Ph 115-118 31 0 MeS CH2S 2-Me-Ph 82-86 32 0 Cl CR2S 2-benzothiazolyl 95-97 33 0 MeO C=-C Ph 164-166 34 0 MeO CH2ON=C(Me) 4-Br-Ph 115-120 35 0 Cl CH2ON=C(Me) 4-Br-Ph gum' 36 0 CI CH2O 3-(benzoyl)-Ph oil 37 O MeS CH2ON=C(Me) 4-Br-Ph 117-122 38 0 MeO CH2O 3-(benzoyl)-Ph 39 0 Cl CH=NOCH2 4-CI-Ph 40 O Cl CH2ON=C(Me) 1,3-benzodioxol-5-yl 41 0 MeO CH=NOCH2 4-Cl-Ph oil' 42 O MeO CH2ON=C(Me) 1,3-benzodioxol-5-yl oil* 43 O Cl O 6-PhO-4-pyrimidinyl oil* 44 0 MeO CH2S 2-benzothiazolyl 95-97 45 0 MeO CH2ON=C(Me) 2-Me-Ph oil* 46 0 MeO CH20N=C(Me) 4-CF3-Ph 138-144 47 0 MeO CH2ON=C(CF3) Ph oil* 48 0 MeO CH2ON=C(Me) Ph oil* 49 0 MeO CH2ON=C(Me) 3-Me-Ph oil* 50 0 MeO CH20N=C(Me) 4-MeO-Ph oil'..

51 O MeO CH2ON=C(Me) 3-Cl-Ph oil* 52 0 MeO CH=NOCH(Me) Ph oil* 53 0 MeO CH=NOCH2 2-Me-Ph oil* 54 O Cl O Ph solid* 55 O Cl - CH2Cl:CH2Br(60:40) solid* 56 0 MeO - CH2Br solid* 57 0 Cl O Me 152-154 58 0 Cl CH2ON=C(Me) 4-CF3-Ph 111-118 59 O MeO CH2ON=C(Me) 3-CF3-Ph 103.5- 105.5 60 0 MeS CH2ON=C(Me) 4-CF3-Ph oil* 61 O MeO CH2ON=C(CF3) 3-CF3-Ph oil* 62 0 MeO O 6-(2-CN-PbO)-4- solid/gum* pyrimidinyl 63 0 MeO O 6-CI-4-pyrimidinyl 133-136 64 0 MeO O 6-(2-Me-PhO)-4- solid/gum* pyrimidinyl 65 0 MeO O 6-PhO-4-pyrimidinyl gum* 66 0 MeO CH20N=C(Me) 2-pyridinyl 122-124 67 0 Cl CH20N=C(Me) 4-pyridinyl 153-155 68 0 MeO CH2O 2,5-diMe-Ph 130-135 69 0 MeO CH20N=C(Me) 4-t-Bu-Ph gum* 70 0 MeO CH20N=C(Me) 3,4-diMe-Ph gum* 71 0 MeO OCH2 2,5-diMe-Ph 119-122 72 0 MeO CH20N=C(Me) 3,4-diCI-Ph 128-129 73 0 MeO CH20N=C(Me) 3-pyridinyl 90-109 dec.

74 0 MeO CH20N=C(Me) 4-pyridinyl 140-142 75 0 Cl 0 6-CI-4-pyrimidinyl solid* 76 O MeO CH2ON=C(Me) 4-Ph-Ph about 55* 77 0 Cl CH2O 2,5-diMe-Ph solid* 78 0 Cl CH20N=C(Me) l-Me-3-pyrrolyl 124-131 79 0 MeO CH20N=C(Me) l-Me-3-pyrrolyl 135-137.5 80 0 Cl CH2ON=C(Me) 2-pyrazinyl 108-111 81 0 MeO CH20N=C(Me) 2-pyrazinyl 119- 12 1 82 0 Cl CH20N=C(Me) 3,5-diCF3-Ph oil* 83 0 MeO CH20N=C(Me) 3,5-diCF3-Ph 147-149 84 0 MeO CH2ON=C(c-Pr) 4-CI-Ph oil 85 O MeSO2 CH2ON=C(Me) 4-CF3-Ph 50-55 86 O MeS(O) CH2ON=C(Me) 4-CF3-Ph oil/gum 87 0 MeO CH2ON=C(Me) 6-Me-3-pyridinyl 134-136 88 0 MeO CH20N=C(Me) 3-t-Bu-Ph oil* 89 0 MeO CH2ON=C(Me) 3-Ph-Ph oil 90 0 MeO CH20N=C(Me) 3-i-PrO-Ph oil 91 0 MeO CH2ON=C(Me) 4,6-diMe-2-pyrimidinyl 119-121 92 0 MeO CH2ON=C(Me) 3-CF30-Ph 90-92 93 0 MeO CH20N=C(Me) 3-Me2N-Ph 106-110 94 0 Cl CH2ON=C(Me) 3,4-diCl-Ph solid* 95 0 MeO CH20N=C(Me) 4-CF3-2-pyridinyl 144-145 96 O MeO CH2ON=C(Me) 3-n-C4F9-Ph oil* 97 0 MeO CH20N=C(Me) 4-CN-2-pyridinyl 12()- 125 98 0 MeO CH20N=C(Me) 3-PhO-Ph 99 O MeO CH2ON=C(Et) 3-CF3-Ph oil 100 0 MeO CH2ON=C(Me) 3-NO2-Ph gum 101 0 MeO CH20N=C(Me) 4-Ph-2-pyridinyl 115-117.5 102 0 MeO CH20N=C(Me) 2-thienyl I ()()- 105 103 0 MeO CH20N=C(Me) 4-t-Bu-2-pyridinyl 103-105.5 104 0 MeO CH2ON=C(Me) 2-benzofuranyl 149- 154 105 0 MeO CH2ON=C(Me) 5-Cl-3-Me- 167-169 benzo[b]thiophen-2-yl 106 0 MeO CH20N=C(Me) 3,5-diCl-Ph 149-153 107 0 MeO CH20N=C(Me) 2,4-diMe-5-thiazolyl 123-124 108 0 Cl CH20N=C(Me) 2-quinoxalinyl 173-174 109 0 MeO CH2ON=C(Me) 2-quinoxalinyl 225-227 110 0 MeO CH20N=C(Me) 3,5-diMe-Ph oil 111 0 Cl CH20N=C(Me) 3-CF3-Ph oil; 112 0 Cl CH2ON=C(c-Pr) 4-Cl-Ph 113 0 MeO CH20N=C(Me) 3-CN-Ph gum 114 0 Cl CH2O 5-Me-2-(2-pyridinyl)-4- oil* thiazolyl 115 0 MeO CH20N=C(Me) 3-F-5-CF3-Ph oil* 116 0 MeO CH20N=C(CN) 3-CF3-Ph 138-141 117 0 MeO CH20N=C(Me) 6-Me-2-CF3-thiazolo[2,3- 157-160 c]-1,2,4-triazol-5-yl 118 0 MeO CH20N=C(Me) 35-diF-Pb 103-106 119 0 MeO CH20N=C(Me) 3,5-diBr-Ph 139-141 120 0 MeO CH20N=C(Me) 2-quinolinyl I 68- 171 121 0 Cl CH20N=C(Me) 3-CF30-Ph 184 O MeO CH2ON=C(Me) 4-EtO-2-pyrimidinyl 75-78 185 0 MeO CH20N=C(c-Pr) 2-thienyl 137-139 186 0 MeO CH2ON=C(Me) 2-Ph-4-thiazolyl 112-113 187 0 MeO 0 3-[3,5- 139.5- Ex. 1 bis(trifluoromethyl)- 141.5 phenyl]-1,2,4- thiadiazol-5-yl 188 0 MeO CH20N=C(Me) 6-Br-2-pyridinyl 151-153 189 0 MeO CH2ON=C(OMe) Ph oil* 190 0 MeO CH20N=C(Me) 3-Br-Ph oil 191 0 MeO CH20N=C(Me) 4-C02Et-2-pyridinyl 133-134 192 0 MeO CH=NOCH(Me) 3-CF3-Ph oil* 193 0 Cl 0 3-PhO-Ph oil' 194 O MeO O 3-PhO-Ph oil* 195 0 MeO CH20N=C(Me) 4-CO2Me-2-pyridinyl 150-151.5 196 0 MeO CH20N=C(Me) 5-Me-1-Ph-1H-pyrazol-4- 45-49 yl 197 0 MeO CH2ON=C(Me) 4-CF3-2-pyrimidinyl 103-105 198 0 MeO CH2ON=C(Me) 3-I-Ph oil* 199 0 MeO CH20N=C(OMe) 2,6-diCl-4-pyridinyl oil* 200 0 MeO CH20N=C(OMe) 3-CF3-Ph oil* 201 0 F2CHO direct bond Me solid* 202 0 MeO CH2ON=C(Me) 2-Cl-4-pyrimidinyl 195-200 203 0 Cl CH2ON=C(OMe) 2,6-diCl-4-pyridinyl oil* 204a O F2CHO CH2ON=C(Me) 3-CF3-Ph oil* 205 O Cl CH2ON=C(Me) 3,5-diCl-Ph gum* 206 0 MeO CH20N=C(Me) 2-naphthalenyl 91-94 207 0 MeO CH2ON=C(Me) 5,6,7,8-tetrahydro-5,5,8,8- 50* tetramethyl-2- naphthalenyl 208 0 MeO CH20N=C(Me) 5,6,7,8-tetrahydro-2- 106-109 naphthalenyl 209 0 MeO CH2SC(Et)=N 4-Cl-Ph gum* 210b 0 MeO CH=C(Cl)C(=O)O t-Bu semi- solid 211 O MeO CH2ON=C(CN)C(=O) 3-CF3-Ph gum* 212 0 MeO CH20N=C(SMe) 3,4-diCI-Ph solid: 213 O MeO C(=O) Ph 126-134 214 0 MeO CH20N=C(S02Me) 3,4-diCl-Ph semi- solid* 215 O MeO CH2SC(Me)=N 3-CF3-Ph oil* 216 0 MeNH CH2O 2,5-diMe-Ph 131-136 217 0 MeNH CH2ON=C(Me) 5,6,7,8-tetrahydro-5,5,8,8- about 50* tetramethyl-2- naphthalenyl 218 S CF3 direct bond Me 79-83 219 0 CF3 direct bond Me 73-77 220 0 CF3 0 3-PhO-Ph oil* 221 S CF3 CH2O 2,5-diMe-Ph gum* 241 0 MeO CH20 2-CN-2-(3-CF3- 115-118 Ph)ethenyl 242 0 MeO CH2CHN I 36-I 35 CF3 243 0 MeO CH20-N=C(CH3)CH20 3-CF3-Ph oil* 244 0 MeO CH2O-N=C(CH3)CH2S 1-CH3-1H-tetrazol-5-yl oil* 245 0 MeO CH20-N=C(CH3) 2,6-diCl-4-pyridinyl 144-146 246 0 MeO CH2O-N=C(CH3)CH2S 2-benzoxazolyl oil* 247 0 MeO CH20-N=C(SCH3) 3,5-diCl-Ph oil* 249 0 MeO CH2O-N=C(CH3)CH2O 3,5-diCl-Ph oil* 250 0 MeO CH2S-C(CH2CH3)=N 3-CF3-Ph oi 251 0 MeO CH2O-N=C(H) 3,5-diCF3-Ph ì 15-1 IX 252 0 MeO CH2O-N=C(CH3) 2,6-diCl-4-pyridinyl oil* 253 0 MeO CH2O-N=C(CH3) 4-(C02-t-Bu)-2-pyridinyl 174-175 254 0 MeO CH20-N=C(OCH3) 3,5-diCl-Ph oil 255 0 Cl 0 3-MeO-Ph oil* 256 0 MeO CH2O-N=C(CH3) 2,6-diCl-4-pyrimidinyl 139-140 257 O MeO CH2O-N=C(CH3) 5,6-diCl-3-pyridinyl 130-132 258C 0 MeO CH2O-N=C(CH3) 5,6-diCl-3-pyridinyl 112-13() 259 0 Cl CH20-N=C(CH3) CH3 oil' 260d O MeO CH2O-N=C(CH3) 2,6-diCl-4-pyrimidinyl 93-123 261 O MeO CH2O-N=C(CH3) 3-CF3-4-MeO-Ph 112-121 262 0 MeO CH20-N=C(CH3) 3-CF3-4-F-Ph 263 0 MeO O 5-Ph-1,3,4-oxadiazol-2-yl 13()-139 264 O MeO O 5-(4-Me-Ph)-1,3,4- 150-151 oxadiazol-2-yl 265 O MeO O 5-(4-Br-Ph)-1,3,4- solid* oxadiazol-2-yl 266 0 MeO O 5-(4-Cl-Ph)-1,3,4- 130-132 Ex. 3 oxadiazol-2-yl 267 0 MeO O 5-(3-MeO-Ph)-1,3,4- 108-111 oxadiazol-2-yl 268 0 MeO O 5-(3-Me-Ph)-1,3.4- 119-121 oxadiazol-2-yl 269 0 MeO O 5-(4-t-Bu-Ph)-1,3,4- 159-161 oxadiazol-2-yl 270 0 MeO o 5-(3-F-Pb)- 1,3.4- 105-1 ()X oxadiazol-2-yl 271 0 MeO O 5-(4-F-Ph)-1,3,4- 124-125 oxadiazol-2-yl <BR> <BR> 272 0 MeO O 5-(3-Cl-Ph)-1,3,4- 1 3()- 135 oxadiazol-2-yl 273 0 MeO O 5-(4-CF3-Ph)-1,3,4- solid oxadiazol-2-yl 274 0 MeO Cll2CHN 1(11- lOS 275 0 MeO O 3-(2-CN-PhO)-Ph oil* 276 0 MeO O 3-(2-N02-PhO)-Ph oil* 277 0 MeO O 3-(3-N02-2-pyridinyl-0)- oil* Ph 278 0 Cl CH20-N=C(CH3) 4-CF3-2-pyridinyl 85-86 279 0 MeO O 5-(3-Br-Ph)-1,3,4- 147-157 oxadiazol-2-yl 280 0 MeO O 3-(3-N02-Ph)-1,2,4- 169-170 thiadiazol-5-yl 281 0 MeO CH2O-N=C(OCH3) 3,5-diCF3-Ph oil* 282 0 MeO CH20-N=C(CH3)CH2S 3,5-diCF3-Ph oil* 283 O MeO CH2O-N=C(CH3)CH2O 3,5-diCF3-Ph oil* 284e O MeO CH2O-N=C(CH3) 2,8-diCF3-quinolin-4-yl 149-151 285f 0 MeO CH20-N=C(CH3) 2,8-diCF3-quinolin-4-yl 150-155 286 O MeO CH2O-N=C(CH3) 5-Br-3-pyridinyl 120-122 287 0 MeO O 3-(3-Cl-Ph)-1,2,4- 121-122 thiadiazol-5-yl 288 0 MeO O 3-(4-CF3-Ph)-1,2,4- 135-136 thiadiazol-5-yl 289 0 MeO O 3-(4-Me-Ph)-1,2,4- 139-142 thiadiazol-5-yl 290 0 MeO O 3-(4-Br-Ph)-1,2,4- 137 thiadiazol-5-yl 291 0 MeO O 3-(3-Me-Ph)-1,2,4- 125-126 thiadiazol-5-yl 292 0 MeO O 3-(3,4-diF-Ph)-1,2,4- 140-141 thiadiazol-5-yl 293 0 MeO O 3-(3-Cl-4-Me-Ph)-1,2,4- 113-115 thiadiazol-5-yl 294 0 MeO O 3-(3,5-diBr-4-MeO-Ph)- 178-179 1,2,4-thiadiazol-5-yl 295 O MeO O 3-(3,4-diCl-Ph)-1,2,4- 156-158 thiadiazol-5-yl 296 0 MeO O 3-(3,4-diF-Ph)-1,2,4- 142-144 thiadiazol-5-yl 297 O MeO O 3-(4-NO2-Ph)-1,2,4- 192-193 thiadiazol-5-yl 298g 0 MeO CH20-N=C(SCH3) 3-CF3-Ph 299 0 MeO CH2O-N=C(CH3)CH2S 2-benzothlazolyl oil* 300 0 MeO CH20-N=C(OCH3) 2-naphthalenyl oil* 301 0 MeO O 3-(4-CN-PhO)-Ph oilX 302 0 MeO O 3-(4-N02-PhO)-Ph oil 303 0 MeO O 3-F-2-N02-Ph 11 8-120 304 0 MeO O 6-(3-CF3-Ph)-pyrimidin- 123-I 26 4-yl 305 0 MeO O 4-CF30-Ph oil* 306 0 Cl 0 3-(3,5-diCF3-Ph)-1,2,4- 48-51 thiadiazol-5-yl 307 0 MeO CH20-N=C(CH3) 6-MeO-pyridin-3-yl oil* 308 O MeO CH2O-N=C(CH3)CH2S 3,5-diCl-Ph oil* 309 0 MeO O 3-(4-CI-3-F-Pb)- 1.2.4- 137-138 thiadiazol-5-yl 310 0 MeO O 3-(3-MeO-Ph)- 1,2,4- 97-98 thiadiazol-5-yl 311 0 MeO O 3-(4-F-Ph)-1,2,4- thiadiazol-5-yl 312 0 MeO O 5-(3,4-diCl-Ph)-1,3,4- 152-155 oxadiazol-2-yl 313 0 MeO O 6-(3,5-diCF3-Ph)- 168-170 pyrimidin-4-yl 314 0 MeO O 3-(2-pyridinyl-0)-Ph oil* 315 O MeO O 3-(2-pyrimidinyl-O)-Ph oil* 316 0 MeO O 6-(4-Me-PhO)-pyrimidin- oil 4-yl 317 0 MeO O 6-Cl-pyrazin-2-yl 135-137 Ex. 15 318 0 Cl CH2S 5,7-diMe-6-Ph- 121-124 [1,2,4]triazolo[1,5- a]pyrimidin-2-yl 319 0 MeO CH2S 5,7-diMe-6-Ph- 155-1 [1,2,4]triazolo[1,5- a]pyrimidin-2-yl 320 0 MeO O 3-(4-Ph-Ph)-1,2,4- 159-1 thiadiazol-5-yl 321 0 MeO O 3-(3-CF3-Ph)-1,2,4- 122-123 thiadiazol-5-yl 322 0 MeO O 3-(4-t-Bu-Ph)-1,2,4- 174-175 thiadiazol-5-yl 323 0 MeO O 3-(3-Br-Ph)-1,2,4- 137-139 thiadiazol-5-yl 324 0 MeO O 3-(3-Br-4-MeO-Ph)-1,2,4- 161-162 thiadiazol-5-yl 325 0 MeO O 3-(4-F-3-CF3-Pb)-i,2,4- 164-165 thiadiazol-5-yl 326 O MeO O 3-(4-Br-3-Me-Ph)-1,2,4- 160-162 thiadiazol-5-yl 327 0 MeO O 5-(4-MeO-Ph)- 1.3.4- 1 X()- 1 I oxadiazol-2-yl 328 O MeO O 5-(4-Ph-Ph)-1,3,4- 179-180 oxadiazol-2-yl 329 0 MeO O 3-(3,4-diCl-Ph)-1,2,4- 159-160 thiadiazol-5-yl 330 0 MeO O 5-(3,5-diCF3-Ph)-1,3,4- 175-176 oxadiazol-2-yl 331 0 MeO O 5-(2-F-Ph)-1,3,4- 139-140 oxadiazol-2-yl 332 0 MeO O 5-(2-Cl-Ph)-1,3,4- 139-140 oxadiazol-2-yl 333 O MeO O 5-(2,4-diCl-Ph)-1,3,4- 181-182 oxadiazol-2-yl 334 O MeO O 3-(4-MeS-Ph)-1,2,4- solid* thiadiazol-5-yl 335 0 MeO O 3-(3-F-Ph)-1,2,4- 116-118 thiadiazol-5-yl 336 0 MeO O 3-CF3-Ph solid* 337 0 MeO O 5-(4-Cl-Ph)-1,3,4- solid* Ex. 18 thiadiazol-2-yl 338 0 MeO O 6-F-pyridin-2-yl 175-I 339 0 MeO O 6-(3-Me-PhO)-pyrimidin- oil 4-yl 340 0 MeO CH2 3-(4-Cl-Ph)-1 H-pyrazol- I I59-1 yl 341 0 MeO O 3-(4-Cl-Ph)-1,2,4- 126-127 thiadiazol-5-yl 342 0 MeO O 3-(4-CF3O-Ph)-1,2,4- solid* thiadiazol-5-yl 343 0 MeO O 3-(3-CF3O-Ph)-1,2,4- 112-113 Ex. 2 thiadiazol-5-yl 344 0 MeO O 3-(4-HCF2O-Ph)- 1,2,4- solid thiadiazol-5-yl 345 O MeO O 3-t-Bu-1,2,4-thiadiazol-5- 110-111 Ex. 14 yl 346 0 MeO CH20-N=C(CH3) 4-(CF3CH2O)-3-CF3-Ph oil' 347 0 MeO CH20-N=C(OCH3) 3-Br-Ph 348 O MeO O 6-(4-CF3-Ph)-pyrimidin- 163-165 4-yl 349 O MeO O 3-(2-CHO-PhO) 106-108 350 0 MeO O 3-(2-Me-PhO)-2-N02-Ph 131-133 351 O MeO O 5-NO2-6-PhO-pyridin-2- 127-130 yl 352 0 MeO O 3-(2-Me-PhO)-Ph oil* 353 0 MeO O 3-c-Pr-l ,2,4-thiadiazol-5- * yl 354 0 MeO O 3-c-pentyl-1,2,4- * thiadiazol-5-yl 355 0 Cl CH2 3-(4-Cl-Ph)-1H pyrazol-1- * yl 356 O MeO O 4-(4-Cl-Ph)-1,2,5- * thiadiazol-3-yl 357 0 MeO OCH2 2-Cl-5-thiazolyl * 358 0 MeO O 6-(4-CF3-Ph)-2-pyrazinyl 145-148 Ex. 16 359 0 MeO CH2O 5-CF3-2-pyridinyl 128-130 360 O MeO CH2O-N=C(CH3) 3-[t-BuOC(=O)-Ph gum* 361 0 MeO O 6-(3,5-diCF3-Ph)-2- 173-174 pyrazinyl 362 0 MeO O 6-(2,4-diCI-Ph)-4- 170-175 pyrimidinyl 363 O Cl O 3-(3-CF3O-Ph)-1,2,4- thiadiazol-5-yl 364 0 Cl 0 3-(3,4-diCl-Ph)-1,2,4- thiadiazol-5-yl 365 0 Cl 0 3-(3,5-diCl-Ph)-1,2,4- 149-150 thiadiazol-5-yl 366 0 Cl 0 3-(4-Br-Ph)-1,2,4- 158-159 thiadiazol-5-yl 367 0 Cl 0 3-(4-CF3-Ph)-1,2,4- * thiadiazol-5-yl 368 0 Cl 0 3-(4-t-Bu-Ph)-1,2,4- * thiadiazol-5-yl 369 0 Cl 0 3-t-Bu- 1 ,2,4-thiadiazol-5- yl 370 0 MeO O 6-PhO-2-pyridinyl oil" 371 O MeO O 3-(4-Me-PhO)-2-NO2-Ph 150-152 372 0 MeO O 3-(2-C02Me-6-N02- oil PhO)-Ph 373 0 MeO CH20-N=C(SCH3) 3,5-diCF3-Ph solid 374 0 MeO CH2O-N=C(CH3) 4-Me3Si-benzyl oil 375 0 Cl CH20-N=C(CH3) 4-Me3Si-benzyl oil 376 0 MeO O 3-(3-CN-2-pyridinyl-0)- 132-134 Ph 377 0 MeO O 6-Cl-3-NO2-2-pyridinyl 146-151 378 0 MeO O 3-(3,5-diCF3-Ph)-Ph 52-57 379 0 MeO CH2O-N=C(CH3) 4-(C02-n-Bu)-2-pyridinyl 106-108 380 O MeO CH2O-N=C(CH3) 4-(CO2-i-Bu)-2-pyridinyl 147-149 381 0 MeO O 5-(3-Br-Ph)-1,3,4- oil* thiadiazol-2-yl 382 0 MeO O 3-(6-Cl-5-NO2-4- 70-74 pyrimidinyl-O)-Ph 383 0 Cl O 2-naphthalenyl 147-150 384 0 MeO O 2-naphthalenyl oil* 385 0 MeO O 3-I-Ph 126-128 386 0 MeO O 3-(4-Me-Ph-O)-Ph oil 387 0 MeO O 3-(2-CO2Me-Ph-O)-Ph oil* 388 0 MeO O 3-(2,6-diCN-Pb-O)-Pb 65-68 389 0 MeO O 3-(3-Me-Ph-O)-Ph oil 390 0 MeO O 4-(3-Cl-Ph)-1,2,5- thiadiazol-3-yl 391 0 MeO CH2 3-(3-Cl-Ph)-1H-pyrazol-1- * yl 392 0 MeO O 6-CI-2-benzothiazolyl solid* 393 0 MeO O 5-MeSO2-1,3,4- * oxadiazol-2-yl 394 0 Cl O 5-MeSO2-l,3,4- * oxadiazol-2-yl 395 0 Cl O 3-(4-CF3O-Ph)-1,2,4- thiadiazol-5-yl 396 0 MeO O 5-(2-Br-Ph)-1,3,4- * thiadiazol-2-yl 397 0 MeO O 5-(2-Cl-Ph)-1,3,4- thiadiazol-2-yl 398 0 MeO CR2S 5-Ph-2-benzoxazoìyl 55 399 0 MeO OCH2 5.7-diCI-2-benzoxazolyl 173-175 400 0 MeO CH2O-N=C(OCH3) 3-Br-5-1-Ph oil 401 0 MeO CH2O-N=C(OCH3) 3-F-5-CF3-Ph oil 402 0 MeO CR2S 5-CI-2-benzothiazolyl solid* 403 0 MeO O 4-Cl-2-benzothiazolyl 178-181 404 0 MeO O 4-(3-CF3-Ph)-2- 50 pyrimidinyl 405 O MeO OCH2 5-(3-CF3-Ph)-1,2,4 118-150 oxadiazol-3-yl 406 O MeO OCH2 2-(4-Cl-Ph)-4-thiazolyl * 407 O MeO O 6-Cl-pyridinyl 161-163 408 0 MeO O 3-(4-CF3-Ph)-Ph 149-152 409 0 MeO O 6-(3,5-diCF3-Ph)-2- 176-178 pyridinyl 410 0 MeO O 5-(2-F-Ph)-1,3,4- oil thiadiazol-2-yl 411 0 MeO O 5-(4-Br-Ph)-1,3,4- solid thiadiazol-2-yl 412 O MeO O 5-(4-t-Bu-Ph)-1,3,4- solid* thiadiazol-2-yl 413 0 MeO O 5-Br-4-(3.4-diF-Ph )-2- 155-157 thiazolyl 414 0 MeO O 3-(3,5-diCI-Ph)-Ph 145-147 415 0 MeO O 3-(4-F-PhO)-Ph oil' 416 0 MeO O 3-(4-F-PbO)-2-N02-Pb 105-108 417 0 MeO O 6-(2-Me-PhO)-2-pyridinyl oil 418 O MeO O 3-(2-F-PhO)-Ph oil* 419 0 MeO O 3-(4-NO2-2-CF3-PhO)-Ph oil W 420 0 MeO O 3-(2-MeO-PhO)-Ph oil* 421 0 MeO O 3-(2-MeO-PhO)-2-N02- oil* Ph 422 0 MeO O 3-(3-N02-2-thienyl-0)-Ph oil 423 0 MeO O 3-(2-CF3-PhO)-Ph oil 424 0 MeO O 3-(2,6-diMe-PhO)-Ph oil* 425 0 MeO O 5-(3,5-diCl-Ph)-1,3,4- * thiadiazol-2-yl 426 O MeO O 2-Cl-4-pyrimidinyl 156 158 427 0 Cl 0 3-(4-CF3O-Ph)-1,2,4- thiadiazol-5-yl 428 0 MeO O 5-(3-Cl-Ph)-1,3,4- thiadiazol-2-yl 429 0 MeO O 2-(3,5-diCF3-Ph)-4- 107-113 pyrimidinyl 430 0 MeO CH2O 3-Ph-Ph gum* 431 0 MeO O 5-Cl-2-pyrimidinyl 171-173 432 0 MeO OCH2 5-Ph-2-oxazolyl 15ü- 152 433 0 MeO CH=N-N(CH3) 3-CF3-2-pyridinyl 185-187 <BR> <BR> <BR> 434 0 MeO CH=N-N(CH3) 4-CF3-2-pyridinyl I 5 ')- 171 435 0 Cl CR2S 4.5-dihydro-3-Ph-1,2,4- 79-95 triazin-6-yI 436 O MeO CH2S 3-(3,5-diCl-Ph)-4,5- 174-179 dihydro-1,2,4-triazin-6- yl 437 0 MeO CR2S 4,5-dihydro-3-(3-CF3- 63-72 Ph)-1,2,4-triazin-6-yl 438 0 MeO O 6-(4-CF3-Ph)-2-pyridinyl 75-85 439 0 MeO O 3-(3-CF3-Ph)-Ph 43-45 440 0 MeO O 3-(4-CN-Ph)-Ph 170-171 441 0 MeO CH20-N=C(CH3) 4-Br-2-pyridinyl 96-99 442 0 MeO CH20-N=C(OCH3) 3-CHC12-Ph oil* 443 0 MeO O 4-(3,5-diCF3-Ph)-2- 157-159 pyrimidinyl 444 O MeO CH2O 2-Me-5-t-Pr-Ph 84-86 445 0 MeO O 5-Br-2-thlazolyl 153-I 56 446 O MeO O 5-(3-CF3-Ph)-2-thiazolyl 124-127 447 0 MeO O 3-(2-Br-PhO)-Ph oil* 448 0 MeO O 3-(2-Et-PhO)-Ph oil* 449 0 MeO O 3-Br-1,2,4-thiadiazol-5-yl * 450 0 MeO CH2O 2-Cl-5-CF3-Ph 143-149 451 0 MeO O 5-(3-CF3-Ph)-2- 145-147 pyrimidinyl 452 0 MeO 0 3-(3-thienyl)-1,2,4- solid thiadiazol-5-yl 453 0 MeO O 3-(2-thienyl)-1,2,4- solid thiadiazol-5-yl 454 0 MeO O 5-(2,4-diCl-Ph)-1,3,4- * thiadiazol-2-yl 455 0 MeO O 5-(3,5-diCF3-Ph)-1,3,4- thiadiazol-2-yl 456 0 MeO O 6-(4-CN-Ph)-4- 149-151 pyrimidinyl 457 0 MeO O 6-(3-CF3-Ph)-2-pyrazinyl 118-121 458 0 MeO O 6-(4-CN-Ph)-2-pyrazinyl 195-199 Ex. 17 459 0 MeO O 6-(3-Cl-4-F-Ph)-2- 147-139 pyrazinyl 460 O MeO CH2O-N=C(CH3) 4-(C#CH)-2-pyridinyl 99-102 461 0 MeO O 5-Br-2-pyrimidinyl 172 174 462 0 MeO O 3-(5-Br-2-thienyl)-1,2,4- Ex. 12 thiadiazol-5-yl 463 O MeO CH2S 3-(3-Cl-Ph)-4,5-dihydro- 65-78 5-Me-1,2,4-triazin-6-yl 464 O Cl CH2S 3-(3-Cl-Ph)-4,5-dihydro- 171-172 5-Me-1,2,4-triazin-6-yl 465 O Cl CH2S 3-(3,5-diCl-Ph)-1,2,4- 108-111 thiadiazol-5-yl 466 0 MeO O 5-(4-CF3-Ph)-1,3,4- * thiadiazol-2-yl 467 O MeO O 5-Br-4-(3-CF3-Ph)-2- gum* Ex. 19 thiazolyl 468 0 MeO O 7-MeO-2-naphthalenyl 469 O MeO O 3-(2-CN-3-F-PhO)-Ph oil* 470 0 MeO O 3-(2-CN-6-F-PhO)-Ph oil 471 0 MeO O 3-(2,6-diNOo-PhO)-Ph oil* 472 0 MeO O 3-(2,5-diF-PhO)-Ph oil 473 0 MeO O 3-(2,5-diMe-PhO)-Ph oil' 474 0 MeO O 3-(2,5-diCI-3-thienyl)- 144-147 Ex. 13 1,2,4-thiadiazol-5-yl 475 0 MeO O 3-(4-1-Ph)- 1,2,4- 167-168 thiadiazol-5-yl 476 0 MeO O 3-(6-Cl-3-pyridinyl)- 169-170 1,2,4-thiadiazol-5-yl 477 0 MeO O 3-(3-I-Ph)-1,2.4- 171-172 thiadiazol-5-yl 478 0 MeO O 4-(3-CF3-Ph)-2-thiazolyl 116-118 Ex. 20 479 0 MeO CH2O-N=C(CH3) 3,4-dihydro-4,4-diMe-2H- oil* 1-benzothiopyran-6-yl 480 0 MeO CH2O-N=C(CH3) 3,4-dihydro-2H-I- oil* benzothiopyran-7-yl 481 0 Cl CH2O-N=C(CH3) 3,4-dihydro-4,4-diMe-2H- oil* 1-benzothiopyran-6-yl 482 0 Cl CH20-N=C(CH3) 3,4-dihydro-2H-1- oil benzothiopyran-7-yl 483 0 MeO CH20-N=C(CH3) 3-(CF3CH2O)-Ph gum 484 0 MeO CH20-N=C(NH2) 3,5-diCF3-Ph 177-178 485 0 MeO O 3-(4,5-diCl-2-tbienyl)- solid' 1,2,4-thiadiazol-5-yl 486 0 MeO CR2S 3-(3,5-diCl-Ph)-1,2,4- 193-195 thiadiazol-5-yl 487 0 MeO CR2S 3-(3-CF3-Ph)-1,2,4- 139-140 thiadiazol-5-yl 488 0 MeO O 3-(3,4,5-triC1-2-thienyl)- 175-177 1,2,4-thiadiazol-5-yl 489 0 MeO O 3-(5-C1-2-thienyl)- 1,2,4- 130-131 thiadiazol-5-yl 490 0 MeO O 3-[3-(PhC#C)-Ph]-1,2,4- * thiadiazol-5-yl 491 0 MeO O 3-[3-(Me3SiC#C)-Ph]- 133-134 Ex. 6 1,2,4-thiadiazol-5-yl 492 0 MeO O 3-[3-(EtOC#C)-Ph]-1,2,4- solid thiadiazol-5-yl 493 0 MeO O 3-[3-(4-F-PhC#C)-Ph]- solid 1,2,4-thiadiazol-5-yl 494 0 MeO O 3-[3-(2-pyridinyl-C#C)- solid* Ph]-1,2,4-thiadiazol-5- yl 495 0 MeO 0 3-[3-(tetrahydropyran-2- solid* yl-OCH2-C=C)-Pb]- 1,2,4-thiadiazol-5-yl 496 O MeO O 3-[3-(t-Bu-C#C)-Ph]- 130-131 1,2,4-thiadiazol-5-yl 497 0 MeO O 3-(3-CHO-Ph)-1,2,4- * thiadiazol-5-yl 498 0 MeO O 3-(2,5-diCl-PhO)-Ph I 10-I 12 499 O MeO O 3-(3,5-diCl-PhO)-Ph oil* 500 0 MeO CH2O 3-(4-CF3-Ph)-1,2,4- 107-111 thiadiazol-5-yl 501 0 MeO CH2O 3-(3,5-diCF3-Ph)-1,2,4- 132-136 thiadiazol-5-yl 502 0 MeO CH20 2-(3-CI-4-MeO-Ph)-5-Me- 172-175 4-thiazolyl 503 0 MeO O 3-(3-CF3-PhO)-Ph 504 0 MeO O 3-(3-F-PhO)-Ph oil 505 0 MeO O 3-(2,3-diF-PhO)-Ph oil* 506 0 MeO O 3-(2,4-diF-PhO)-Ph oil* 507 O MeO O 3-(3-HC#C-Ph)-1,2,4- 177-178 Ex. 7 thiadiazol-5-yl 508 0 MeO O 3-(6-CF3CH2O-3- solid* pyridinyl)- 1,2,4- thiadiazol-5-yl 509 0 MeO O 6-(4-Cl-Ph)-2-pyrazinyl 156-158 510 0 MeO O 6-(4-F-Ph)-2-pyrazinyl 151-153 511 0 MeO O 6-Ph-2-pyrazinyl 135-136 512 0 MeO CH2O-N=C(CH3) 3-Et-Ph 81-85 513 0 MeO CH2S 3-(3,5-diCF3-Ph)-1,2,4- 157-1 59 thiadiazol-5-yl 514 O MeO O 6-(4-Cl-Ph)-4-pyrimidinyl 115-120 515 0 MeO O 5-Me-4-(3-CF3-Ph)-2- oil* Ex. 21 thiazolyl <BR> <BR> <BR> <BR> 516 0 MeO O 6-(4-CO2Et-Pb)-2- l ìt)-127 pyrazinyl 517 O MeO O 3-(5-Br-3-pyridinyl)- 188-189 1,2,4-thiadiazol-5-yl 518 0 MeO O 3-(2,6-diCl-4-pyridinyl)- 148-149 1,2,4-thiadiazol-5-yl 519 0 MeO O 4-CI-5-CN-2-thiazolyl 119-122 520 O MeO O 3-(2-furanyl)-1,2,4- 107-108 Ex. 11 thiadiazol-5-yl 521 0 Cl ;s0 2-thiazolyl 95-100 -CH2N N- (CH2)3 522 0 Cl y 3-CF3-Ph 125-130 -CH2N\ N- (CH2)2 523 0 MeO y 2-thiazolyl 166-170 -CH2N N- (CH2)3 524 0 MeO Y 3-CF<-Ph 13(1-135 -CH2N N- (CH2)2 525 O MeO CH2O 1,6-diBr-2-naphthalenyl 189-191 526 O MeO O 3-(5-Br-2-furanyl)-1,2,4- solid* thiadiazol-5-yl 527 0 MeO O 3-[3-PhC(=O)O-Ph]- * Ex. 8 1,2,4-thiadiazol-5-yl 528 0 MeO O 3-(3-HO-Ph)-1,2,4- solid* Ex. 9 thiadiazol-5-yl 529 0 MeO O 6-Ph-4-pyrimidinyl 123-125 530 0 MeO O 3-(t-Bu-C#C)-1,2,4- * Ex. 5 thiadiazol-5-yl 531 0 MeO O 3-(3-Et3SiO-Ph)-1,2,4- thiadiazol-5-yl 532 0 MeO O 3-[3-(t-BuMe2SiO)-Ph]- 1,2,4-thiadiazol-5-yl 533 0 MeO O 3-[3-Cl3CCH2OC(=O)O- * Ph]-1,2,4-thiadiazol-5- yl 534 0 MeO O 3-[3-MeCHClOC(=O)O- Ph]-1,2,4-thiadiazol-5- yl 535 0 MeO 0 3-[3- X [CH2=CHOC(=O)O]- Ph]-1,2,4-thiadiazol-5- yl 536 0 MeO O 3-[3-[t-BuC(=O)O]-Ph]- * 1,2,4-thiadiazol-5-yl 537 0 MeO 0 3-[3- * [Me3Si(CH2)2OCH2O] -Ph]-1,2,4-thiadiazol-5- yl 538 O MeO O 3-[3-CF3S(O)2O-Ph]- solid* Ex. 10 1,2,4-thiadiazol-5-yl 539 O MeO O 3-(2,5-diBr-3-thienyl)- solid* 1,2,4-thiadiazol-5-yl 540 O MeO O 3-(3-Cl-benzyl)-1,2,4- solid* thiadiazol-5-yl 541 O MeO O 3-(4-Cl-benzyl)-1,2,4- solid* thiadiazol-5-yl 542 0 MeO O 6-(4-F-Ph)-4-pyrimidinyl 65-7() 543 O MeO CH2S 3-(3,5-diCl-Ph)-5-Me- 196-198 1,2,4-triazin-6-yl 544 0 MeO CH2S 4,5-dihydro-5-Me-3-Ph- 66-68 1,2,4-triazin-6-yl 545 0 MeO CR2S 5-Me-3-Ph-1,2,4-triazin- 168-171 6-yl 546 0 MeO CR2S 5-Me-3-(3-CF3-Ph)-1,2,4- 64-66 triazin-6-yl 547 0 MeO O 3-(3-Me3SiO-Ph)-1,2,4- thiadiazol-5-yl 548 0 MeO o 3-[3-(CH2=CHCH20)- Ph]-1,2,4-thiadiazol-5- yl 549 0 MeO o 3-[3-(CH2=CBrCH2O)- Ph]-1,2,4-thiadiazol-5- yl 550 0 MeO O 5-Br-4-(3,5-diCI-Ph)-2- 153-155 thiazolyl 551 O MeO CH2S 3-(3-Cl-Ph)-5-Me-1,2,4- 117-11 trlazin-6-yl 552 0 MeO CH2O-N=C(CH3) t-Bu 96-98 553 0 MeO CH2O CF3CH2 oil- 554 0 MeO o 4-(3,5-diCI-Ph)-2- solid* thiazolyl 555 0 MeO o 4-(3,5-diCl-Ph)-5-Me-2- 60 thiazolyl 556 O MeO O 3-[3-(CH2=CH)-Ph]- * 1,2,4-thiadiazol-5-yl 557 O MeO O 3-[4-(4-F-PhC#C)-Ph]- 154-157 1,2,4-thiadiazol-5-yl 558 O MeO O 5-CN-2-Ph-4-thiazolyl 144-147 559 0 MeO O 3-Et-7-CF3-2- 138-141 quinoxalinyl 560 0 MeO CH2O 3-Et-7-CF3-2- 155-157 quinoxalinyl 561 O MeO O 6-(4-CO2Et-Ph)-4- 147-149 pyrimidinyl 562 0 MeO O 5-Cl-4-(3-CF3-Ph)-2- gum thiazolyl 563 0 MeO O 5-CN-4-Et2N-2-thiazolyl solid* 564 0 MeO O 5-Et-4-(3-CF3-Ph)-2- gum* thiazolyl 565h 0 MeO CH20-N=C(CH3) 3-CF3-Ph 84-87 566 0 MeO CH2O-N=C(OCH3) 4-CF3-2-pyridinyl solid 567 0 MeO O 3-[4-(HC#C)-Ph]-1,2,4- thiadiazol-5-yl 568 0 MeO O 3-[4-(Me3SiC#C)-Ph]- 1,2,4-thiadiazol-5-yl 569 0 MeO 0 3-I-1,2,4-thiadiazol-5-yl solid* Ex. 4 570 0 MeO CH20-N=C(CH3) 4-MeS-Ph oil* 571 0 MeO CH2S-C(SCH3)=N 3-CF3-Ph oil* 572 0 MeO O 3-[3-(Br2C=CH)-Ph]- * 1,2,4-thiadiazol-5-yl 573 0 MeO O 3-[3,5-bis- * [Me3Si(CH2)2OCH2O] -Ph]-1,2,4-thiadiazol-5- yl 574 O MeO direct bond 3-(3-CF3-Ph)-1,2,4- 114-115 oxadiazol-5-yl 575 0 MeO direct bond 5-t-Bu-l,3-benzodioxol-2- oil i yl 576 0 MeO CH2O 1 -(2,4-diC1-Ph)-3-Me- 1 H- glass pyrazol-4-yl 577 0 MeO O 3-[3,5-bis-[CF3CH2O]- * Ph]-1,2,4-thiadiazol-5- yl 578 0 MeO CH20 8-Br-3-Me-6-CF3-2- 180-184 quinoxalinyl 579 0 MeO O 8-Br-3-Me-6-CF3-2- 157-159 quinoxalinyl 582 O MeO CH2S-C(SCH3)=N 4-Br-Ph oil* 581 O MeO CH2S-C(SCH3)=N 3,5-diCl-Ph oil* 582 0 Cl CH2 3-(3,5-diCF3-Ph)-1,2,4- 94-1(13 oxadiazol-5-yl 645 0 MeNH CH2ON=C(CH3) 3-Me3Si-Ph gum* 646 0 MeNH CH2ON=C(CH3) 3,5-diCF3-Ph 140-143 647 S CF3 CH2ON=C(CH3) 3-CF3-Ph 128-131 648 0 CF3 CH20 2,5-diCH3-Ph 162-i 65 649 0 H CH20N=C(CH3) 3,5-diCl-Ph gum* 650 0 MeNH CH20N=C(CH3) 3,5-bis(Me3Si)-Ph gum* 651 0 Et CH20N=C(CH3) 3-CF3-Ph 102-106 652 0 Me2N CH20N=C(CH3) 3-Me3Si-Ph oil* 653 0 Me CH20N=C(CH3) 3-CF3-Ph oil* 654 0 H direct bond CH3 solid" 655 0 Et direct bond CR3 oil' 739 0 CH2=C=CH-O CH20N=C(Me) 3,5-diCF3-Ph oil* 740 0 MeO O 3-(4-Br-Ph)-Ph 60-65 741 0 MeO CH2OC(SMe)=N 3-CF3-Ph 49-5() 742 0 MeO CH2OC(SMe)=N 3,5-diCl-Ph 123-I 25 743 0 Cl CH20N=C(Me)C(Me)=NO Me * 744 0 MeO CH2ON=C(Me)C(Me)=NO Me * 745 0 MeO O 3-(4-C02Et-Ph)-Ph 108-109 746 0 MeO O 3-(4-C02H-Ph)-Ph 172- 174 747 0 MeO CH2SC(SMe)=N (CH3)3CCH2CH2 * 748 0 MeO O 4-t-Bu-5-Br-2-thiazolyl 101-105 749 O MeO O 4-(3,5-diCF3-Ph)-5-Br-2 116-118 thiazolyl 750 O MeO O 4-(3,5-diCF3-Ph)-2- 127-128 thiazolyl 751 0 MeO CH20C(SMe)=N 4-CI-Ph 49-5() 752 0 MeO CH2OC(SMe)=N 3-Cl-Ph 82-84 753 0 MeO O 4-t-Bu-2-thiazolyl 96-98 754 0 MeO CH2O Me 71-73 755 0 MeO CH20-- ::1 49-59 rfllc NO 756 0 MeO CH20-- 53 \ C) 757f 0 MeO CH2ON=C(Me) 4-Ph-3-furazanyl N-oxide 145-147 758e 0 MeO CH2ON=C(Me) 4-Ph-3-furazanyl N-oxide 759 0 MeO O 3-(4-CONH2-Ph)-Ph 760 0 Cl CR2S 5-Ph-1,2,4-triazin-3-yl * 761 0 MeO CH2SC(SMe)=N 2-Me-Ph * 762 0 MeO CH2SC(SMe)=N 3-Me-Ph 763 0 MeO CH2SC(SMe)=N 3-Br-Ph 764 0 MeO CH2OC(=O)NMe 4-CI-Ph 115- 11 7 765 0 MeO O 3-(4-CONMe2-Ph)-Ph 52-56 766 0 MeO O 3-(4-CONHMe-Ph)-Ph 87-92 767 0 MeO O 4-(CF3CH20)-2- * pyrimidinyl 768 0 MeO CH2SC(SMe)=N 2-CI-Ph * 769 0 MeO CH2SC(SMe)=N 4-OMe-Ph * 770 0 MeO CH(Me)ON=C(Me) 3-CF3-Ph 149-152 771 0 MeO direct bond 5-Ph-1,3-benzodioxol-2-yl oil" 772 O MeO OCH2 4-t-Bu-Ph glass* 773 0 Cl S 4,6-diCl-2-benzothiazolyl foam* 774 0 MeO CH20C(SMe)=N t-Bu 775 0 MeO CH20N=C(Me) 3-MeS-Ph 776 0 MeO CH20N=C(CH2Cl) 3-CF3-Ph * 777 0 MeO O 2-CI-4-pyrimidinyl 148-150 778 0 MeO O 6-(CF3CH20)-4- * pyrimidinyl 779 0 MeO CH20N=C(Me) 3-MeS(=O)-Ph * 780 0 MeO CH20N=C(Me) 3-MeS02-Ph * 781 0 MeO CH2ON=C(Me) 3-Ph-5-isoxazolyl 47-51 782i 0 MeO CH20N=C(Me) 3-Ph-5-isoxazolyl 141-144 783 0 MeO CH20N=C(Me) 3-(3-CF3-Ph)-5-isoxazolyl 47-51 784j 0 MeO CH20N=C(Me) 3-(3-CF3-Ph)-5-isoxazolyl 131-133 785 0 MeO O 3-(3-CN-Ph)-1,2,4- 128-132 thiadiazol-5-yl 786 O MeO O 3-(4-CN-Ph)-1,2,4- 155-157 thiadiazol-5-yl 787 O MeO O 3-(3-CO2Me-Ph)-1,2,4- 133-136 thiadiazol-5-yl 788 0 MeO O 4-t-Bu-5-Me-2-thiazolyl 101-103 789 0 MeO CH2ON=C(Me) 3-(4-F-Ph)-5-isoxazolyl 122-140 790k o MeO CH20N=C(Me) 3-(4-F-Ph)-5-isoxazolyl 147-148 791 0 MeO O 3-(3-C02-t-Bu-Ph)-l,2,4- * thiadiazol-5-yl 792 0 MeO CH2O 1-(3-CF3-Ph)-3-Me-1H- pyrazol-4-yl 793 0 MeO O 4-t-Bu-5-CI-2-thiazolyl 115-117 794 0 MeO O 3-t-BuO-1,2,4-thiadiazol- * 5-yl 795 0 MeO O 3-(4-CF3-Ph)-1,2,4- 131-132 oxadiazol-5-yl 796 0 MeO O 3-(3,5-diCF3-Ph)-1,2,4- 119-120 oxadiazol-5-yl 797 0 MeO O 4-(CF3CH2O)-2- * pyrimidinyl 798 0 MeO O 6-(CF3CH2O)-2-pyrazinyl 96-98 799 O MeO O 6-(2-Cl-PhO)-4- oil* pyrimidinyl 800 0 MeO O 6-(2-Et-PhO)-4- pyrimidinyl 801 0 MeO O 6-Me-4-(CF3CH2O)-2- pyrimidinyl 802 0 MeO O 3-CO2Me-6-CF3-2- 140-143 pyridinyl 803 0 MeO O 3-(3-Cl-Ph)-4-CN-5- 181-182 isothiazolyl 804 0 MeO O 3-(4-Cl-Ph)-4-CN-5- 144-147 isothiazolyl 805 0 MeO O 3-(2,4-diCl-PhCR2)- * 1,2,4-thiadiazol-5-yl 806 0 MeO O 3-(3,4-diCI-PhCH2)- * 1,2,4-thiadiazol-5-yl 807 0 MeO O 3-(3-Br-PhCH2)-1,2,4- * thiadiazol-5-yl 808 O MeO O 3-(2-Br-PhCH2)-1,2,4- 138-139 thiadiazol-S-yl 809 0 MeO O 3-(4-Br-PhCH2)-l,2,4- 93-95 thiadiazol-5-yl 810 0 MeO O 3-(3-Me-PhCH2)-1,2,4- 105-107 thiadiazol-5-yl 811 O MeO O 3-(2-Me-PhCH2)-1,2,4- 109-111 thiadiazol-5-yl 812 0 MeO O 3-(4-CF3-PbCH21- 1,2,4- thiadiazol-5-yl 813 0 MeO O 3-(2-CF3-PhCH2)- 1,2,4- 1 4 thiadiazol-S-yl 814 O MeO O 3-(3-F-PhCH2)-1,2,4- 100-101 thiadiazol-5-yl 815 0 MeO O 3-(2-F-PhCH2)-1,2,4- 128-131 thiadiazol-5-yl 816 0 MeO O 3-(3-CF3-PhCH2)-1,2,4- * thiadiazol-5-yl 817 0 MeO O 3-t-Bu-4-CN-5- 150-152 isothiazolyl 818 0 MeO O 6-(2-N02-PbO)-4- 66-7() pyrimidinyl 819 0 MeO O 3-(3,5-diCF3-PhCH2)- 1,2,4-thiadiazol-5-yl 820 0 MeO O 3-(CH2=CHC(Me)2)- 96- I (8) 1,2,4-thiadiazol-5-yl 821 0 MeO O 3-(3-CF3C(=O)NH-Ph)- 1,2,4-thiadiazol-5-yl 822 0 MeO O 3-(3-ClCH2C(=O)NH- Ph)-1,2,4-thiadiazol-5- yl 823 0 MeO O 3-(3-CF3SO2NH-Ph)- * 1 ,2,4-thiadiazoi-5-yl 824 0 MeO O 3-(3-CC13C(=O)NH-Ph)- * 1,2,4-thiadiazol-5-yl 825 0 MeO O 3-(3-NMe2-Ph)-1,2,4- * thiadiazol-5-yl 826 0 MeO CH2ON=C(Me) 3-F2HCO-Ph 827 0 MeO O 4-(3-CF3O-Ph)-5-Br-2- 77-78 thiazolyl 828 0 MeO CH2ON=C(Me) 3-Br-5-isoxazolyl 124- 148 829 0 MeO O 3-(3-CF3C(=O)NMe-Ph)- * 1,2,4-thiadiazol-5-yl 830 0 MeO O 3-(3-CC13C(=O)NMe- * Ph)-1,2,4-thiadiazol-5- yl 831 0 MeO O 4-(3-CF30-Ph)-2- 96-98 thiazolyl 832 0 MeO O 4-(3-CF3O-Ph)-S-Me-2- 88-9(1 thiazolyl 833 0 MeO CH2O 3-Me-2-quinoxalinyl 149-153 834 0 MeO O 3-Me-2-quinoxalinyl 168-170 835 0 MeO O 5-Ph-1,2,4-triazin-3-yl 63-69 836 0 MeO O 5-(3-CF3-Ph)-1,2,4- 64-68 triazin-3-yl 837 0 MeO O 5-(3-Cl-Ph)-1,2,4-triazin- 65-71 3-yl 838 O MeO CH2ON=CH 2-Cl-1-PhCH2-1H-indol- oil* 3-yl 839 O MeO O 5-(4-Cl-Ph)-1,2,4-triazin- 174-181 3-yl 840 0 MeO O 3-(3-CN-Ph)-Ph 161-162 841 0 MeO CH20N=C(Me) 3-(4-pyridinyl)-5- 149-167 isoxazolyl 842 0 MeO CH20-- 51-57 Br 843 0 MeO CR2(mN 132-141 0 844 0 MeO direct bond Ph oil* 845 O MeO direct bond 4-PhO-Ph oil* 846 0 MeO O 3-(3-CF2HCO-Ph)-1,2,4- thiadiazol-S-yl 847 O MeO O 5-(4-F-Ph)-1,2,4-triazin- oil* 3-yl 848 0 MeO O 5-(4-OMe-Ph)-1,2,4- 55-60 triazin-3-yl 849 0 MeO O 3-(3-BrCH=CH-Ph)- 1,2,4- * thiadiazol-5-yl 850 O Cl CH2ON=CH 1H-indol-3-yl 91-94 dec 851 0 MeO O 3-(3-CF3-Ph)-1,2,4- 141-144 oxadiazol-5-yl 852 0 MeO O 3-(3-Br-Ph)-1,2,4- 143-1 oxadiazol-S-yl 853 0 MeO O 3-(3-Cl-Ph)-1,2,4- 121-124 oxadiazol-5-yl 854 0 MeO direct bond 6-Cl-4-pyrimidinyl tacky solid'' 855 0 MeO direct bond 4-Me-2-quinolinyl tacky solid 856 0 MeO O 4-(3-CF3-PhO)-6-MeO-2- oil* triazinyl 857 0 MeO O 3-(2-MeS-Ph)-Ph 58-62 858 0 MeO O 5-(2-Me-Ph)-1,2,4-triazin- oil 3-yl 859 0 MeO CH2ON=C(Me) 3-(4-PhO-Ph)-5- 55-72 isoxazolyl 860 0 MeO CH2ON=C(Me) 3-(4-CI-Ph)-S-isoxazolyl 1 ()3- 125 861 0 MeO CR2(mN 175-170 Cl 862 0 MeO CH2- 157-16() OMe 863 O MeO O 3-(3-ClCH=CH-Ph)-1,2,4- 137-139 thiadiazol-5-yl 864 0 MeO CR2S 5-(3-CF3-Ph)-1,2,4- 138-141 triazin-3-yl 865 0 MeO O 3-(3,5-diCl-Ph)-1,2,4- 181-184 oxadiazol-5-yl 866 0 MeO O 3-(4-Cl-Ph)-1,2,4- 164-167 oxadiazol-5-yl 867 0 MeO CR2CHN 158-160 A MeO 868 O MeO O 4-Cl-Ph 110-112 869 0 MeO O 4-F-Ph 97-99 870 0 MeO O 3-CN-4-cinnolinyl 192-194 871 0 MeO O 4-PhO-6-MeO-2-triazinyl 154-157 872 0 MeO O 4-(4-Me-PhO)-6-MeO-2- 158-160 triazinyl 873 0 MeO O 4-(3-Me-PhO)-6-MeO-2- 140-1 43 triazinyl 874 0 MeO O 3-CF3-1,2,4-triadiazol-5- 118-120 yl 875 0 MeO O 5-Cl-6-Et-4-pyrimidinyl 122-124 876 O MeO O 3,5-diCl-Ph 150-152 877 0 MeO O 5-Et-4-(3-CF30-Ph)-2- thiazolyl 878 0 MeO O 5-SiMe3-4-(3-CF3O-Ph)- 2-thiazolyl 879 0 MeO O 4-(4-Cl-PhO)-6-MeO-2- 166-169 triazinyl 880 0 MeO O 4-(3-NO2-PhO)-6-MeO- 96-100 2-triazinyl 881 0 MeO O 4-(3-OMe-PhO)-6-MeO- 135-139 2-triazinyl 882 0 MeO O 4-(4-F-PhG)-6-MeG-2- 174-177 tri azinyl 883 O MeO O 3-(3-CF3S-Ph)-1,2,4- 75-83 thiadiazol-5-yl 884 O MeO CH2O 3-(t-Bu(Ph)2SiO)-Ph tacky solid* 8851 0 MeO O 4-(3,5-diCF3-Ph)-5-Me- solid* 2-thiazolyl 886 0 MeO direct bond CHCl2 oil* 887 0 MeO O 3-CF3-PhOCH2 100 888 0 MeO O 4-CF3-Ph 109-1 10 889 0 MeO O 3-CN-Ph 112-114 890 0 MeO O 4-(3-CF3-Ph)-2-triazinyl 160-162 891 0 Cl CH2 3-(2-NH2-Ph)-1-H-1,2,4- 197-202 triazol- I -yl 985 O Cl CH2 3-(2-NH2-4-Cl-Ph)-1-H- 180-193 1,2,4-triazol-1-yl 986 O Cl CH2 3-(2-NH2-5-Cl-Ph)-1-H- 80-85 1,2,4-triazol-1-yl 987 O MeO CH2 3-(2-NH2-Ph)-1-H-1,2,4- 178-181 triazol- 1 -yl 988 0 MeO CH2 3-(2-NH2-4-Cl-Ph)-1-H- 80-85 1,2,4-triazol-1-yl 989 0 MeO CH2 3-(2-NH2-5-Cl-Ph)-1-H- 160-165 1,2,4-triazol-1-yl 990 0 MeO O 3-CN-6,7-diF-4- * cinnolinyl 991 0 MeO O 4-t-Bu-5-Et-2-thiazolyl 95-96 992 0 MeO CH2ON=C(Me) 3-(4-Cl-Ph)-4-isoxazolyl 45-52 993 0 MeO CH2ON=C(Me) 2,3-dihydro-2-Me-5- oil* benzofuranyl 994 0 Cl CH2ON=C(Me) 2,3-dihydro-2-Me-5- oil benzofuranyl 995 O MeO O 4-(2-F-PhO)-2-triazinyl 54-59 996 0 MeO CH2O 3-CF3-PbGCH2 oilX 997 0 MeO O t-BuOCH(Me) 89 998 0 MeO CH2O CH3 999 0 MeO CH2ON=C(Me) 3-Ph-4-isoxazolyl * 1000 0 MeO CH2ON=C(Me) 3-(3-CF3-Ph)-4- isoxazolyl 1001 O MeO O 3-(3-Me-Ph)-1,2,4- 100-104 oxadiazol-5-yl 1002 0 MeO O 3-(4-Br-Pb)-l,2,4- 180-182 oxadiazol-5-yl 1003 0 MeO O 3-(3-CN-Ph)-1,2,4- 135-138 oxadiazol-5-yl 1004 0 MeO O 3-(4-CF3O-Ph)-1,2,4- 115-118 oxadiazol-5-yl 1005 O MeO O 3-(4-t-Bu-Ph)-1,2,4- 150-152 oxadiazol-5-yl 1006 0 MeO O 3-(4-CN-Ph)-1.2,4- 175-176 Oxadizol-S-yl 1007 O MeO CH2ON=C(Me) 3-(4-PhOPh)-4-isoxazolyl 50-56 1008 0 MeO CH2CH 157-164 Cl 1009 0 MeO CH2ON=C(Me) 3-Br-4-isoxazolyl 120-139 1010 0 MeO Me CR2N I F 1011 0 MeO O 3-Cl2HC-1,2,4- thiadiazol-5-yl 1012 0 MeO CH2ON=C(Me) 3,4,5-triMeO-Ph 1013 O MeO CH2S 5-(3-Cl-Ph)-1,2,4-triazin- 167-169 3-yl 1014 0 MeO CH2ON=C(Me) 3-(4-Cl-Ph)-4-isoxazolyl 45-52 1015 0 MeO }) 48-53 cH20< r ~\ a Compound contains 15% by weight of 4-[2-(bromomethyl)phenyl]-5- (difluoromethoxy)-2,4-dihydro-2-methyl-3H- 1 ,2,4,-triazol-3-one.

b Compound isolated in a 1:1 ratio of Z and E isomers.

c Compound isolated in a 2:1 ratio of Z and E isomers.

d Compound isolated in a 2:3 ratio of Z and E isomers.

e Compound isolated as the Z isomer.

f Compound isolated as the E isomer.

g Compound isolated in a 1:2 ratio of geometric isomers.

h Compound isolated as the Z isomer.

isomer of Compound 781.

Isomer of Compound 783.

k Isomer of Compound 789.

1 Compound contains 15% by weight of 4-[2-[[4-[3,5-bis(trifluoromethyl)phenyl]-2- thiazolyl]oxy]phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2, 4-triazol-3-one.

*See Index Table M for 1H NMR data.

INDEX TABLE D Cmpd No. W X Y Z m.p. (°C 222 0 MeO CH2ON=C(Me) 3-Me3Si-Ph oil/gum* 223 0 MeO CH2O 2,5-diMe-Ph IS 1-153 224 0 MeO direct bond CH2Br 117-118 225 0 MeO CH2ON=C(Me) 3-CF3-Ph 91-93 226a 0 MeO CH=C(Cl)C(=O)O t-Bu 105-115 227b 0 MeO CH=C(Cl)C(=O)O t-Bu 104 228 0 MeO CH2ON=C(Me) 4-CF3-2-pyridinyl 101-103.5 583 0 MeO direct bond 3-(3-CF3-Pb)- 1 ,2,4-oxadiazol-5-yl 15X 584 0 MeO CH2O-N=C(CH3) 3,4-diCl-Ph 132-134 585 0 MeO CH2O-N=C(NH2) 3-CF3-Ph 123-124 586 0 MeO CH2O-N=C(CH3) 3,5-diBr-Ph 15() 5-1.SI 587 O MeO CH2O-N=C(CH3) 3,5-diCl-Ph 159-160 588 0 MeO CH2O-N=C(CH3) 2-naphthalenyl 124-125 589c 0 MeO CH2O-N=C(CH2CH3) 3-CF3-Ph oil 590 0 MeO CH2O 3-(4-CI-Ph)-1 ,2,4-thiadiazol-5-yl 184-185 591 0 MeO CH2O 3-(3,5-diCl-Ph)-1,2,4-thiadiazol-5-yl 185-186 592 0 MeO CH2O 3-(4-CF3-Ph)-1,2,4-thiadiazol-5-yl 138-139 *See Index Table M for 1H NMR data.

a Compound isolated in a 7:3 ratio of Z and E isomers, respectively.

b Compound isolated in a 5:1 ratio of Z and E isomers, respectively.

c Compound contains 28% by weight of 2,4-dihydro-5-methoxy-2-methyl-4-[5-methyl- 2-[[[[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]meth yl]-3-thienyl]-3H- 1,2,4-triazol-3-one which is also a compound of this invention.

INDEX TABLE E Cmpd W X Y Z m.p. (°C) 229 0 MeO direct bond CH2Br 132-I 33 230 O MeO CH2ON=C(Me) 3,4-diCl-Ph 143-144 231 0 MeO CH2ON=C(Me) 3-Me3Si-Ph oils 232 0 MeO CH2ON=C(Me) 4-CF3-2-pyridinyl 123-125 233 0 MeO CH2ON=C(Me) 3-CF3-Ph 87-89 *See Index Table M for H NMR data.

INDEX TABLE F Cmpd No. W X Y Z m.n. (°C) 234 0 Cl direct bond Me 99-101 235 0 MeO direct bond Me 123-125 236 0 MeO CH2ON=C(Me) 3-CF3-Ph oil* 593 0 MeO CH2O-N=C(CH3) 4-CF3-pyridin-2-yl 106-107 594 O MeO CH2O-N=C(CH3) 3,4-diCI-Ph 102-104 595 0 MeO CH2O-N=C(CH3) 3-Me3Si-Ph 135-137 596 0 MeO CH2O-N=C(CH3) 3,5-diCI-Ph 135-137 597 0 MeO CH2O-N=C(CH3) 3,5-diBr-Ph 145-147 598 0 MeO CH2O-N=C(NH2) 3-CF3-Ph 147-148 599 O MeO CH2S 5-CF3-4H-1,2,4-triazol-3-yl 178-179 600 O MeO direct bond 3-(3-CF3-Ph)-1,2,4-oxadiazol-5-yl 165-166 601 0 MeO CH2 3-CF3-1H-pyrazol-1-yl 99-100 602 0 MeO CH2O 2-CI-5-CF3-Ph 106-108 603 0 MeO CH2O 2,5-diCH3-Ph 91-93 604 0 MeO CH2O-N=C(CH3) 2-naphthalenyl semisolid* 605 0 MeO O 3-PhO-Ph 113-114 606 0 Cl O 3-PhO-Ph 72-75 *See Index Table M for 1H NMR data.

INDEX TABLE G Cmpd No. X Y 7 m.p. ( t.

607 MeO direct bond 3-(3-CF3-Ph)-I ,2,4-oxadiazol-5-yl 149-150 608 MeO direct bond CH2Br 147-149 609 MeO CH2O-N=C(CH3) 2-naphthalenyl 134-136 610 MeO CH2O-N=C(CH3) 3,4-diCI-Ph 118-I IL) 611 MeO CH2O-N=C(CH3) 4-CF3-pyridin-2-yl 125-127 612 MeO CH2O-N=C(CH3) 3,5-diCl-Ph 148.5-150.5 613 MeO CH2O-N=C(CH3) 3-Me3Si-Ph oil* 614 MeO CH2O-N=C(NH2) 3-CF3-Ph semisolid* 615 MeO CH2O-N=C(CH3) 3-CF3-Ph 81-83 616 MeO CH2O-N=C(CH3) 3,5-diBr-Ph 126.5-127.5 *See Index Table M for 1H NMR data.

INDEX TABLE H Cmpd No. X Y Z 617 Cl O Me 142-143 618 MeO O 3-(4-CF3-Ph)-1,2,4-thiadiazol-5-yl 216-217 619 MeO O 3-(3,5-diCl-Ph)-1,2,4-thiadiazol-5-yl 222-223 621 MeO O 3-(4-Cl-Ph)-1,2,4-thiadiazol-5-yl 226 227 621 MeO O Me 180-181 1016 MeO direct bond 4-Cl-Ph 195-197 1017 MeO direct bond 4-CF3-Ph 213-214 1018 MeO direct bond 3,5-diCF3-Ph 222-224 1019 MeO direct bond 3-CF30-Ph 150-151 1020 MeO direct bond 3-C1-4-F-Ph 203-204 1021 MeO direct bond 3-CF3-Ph 144-145 1022 MeO C-C 4-t-Bu-Ph 199-200 1023 MeO C-C t-Bu 196-198 1024 MeO C#C (EtO)2CH glue* INDEX TABLE I Cmpd No. X Y Z m.p. (°C) 622 MeO CH2O-N=C(CH3) 3-CF3-Ph 153-155 INDEX TABLE J t3 g Nt ThYTh X ( /°° AN Rlt N--N I IklOa Me wherein RIOa is Hor R10 CmpdNo. X R9 RlOa y rn.p. (°C) 623 Cl H H CH20 159-162 624 Cl 5-Me 7-Me CH20 204-209 625 Cl 6-Cl H CH20 175-181 626 MeO 5-Me 7-Me CH20 187-197 627 MeO 7-MeO H CH20 207-210 628 MeO 6-Br 7-Me CH20 205-209 629 MeO 5-Me H CH2O 205-208 630 MeO 5-Me 6-Me CH2O 210-214 631 MeO 5-Me 7-Me 0 210-216 632 MeO 7-MeO H O 191-192 633 MeO 7-Cl H CH20 225-229 634 MeO 6-Me 7-Me 0 218-219 635 MeO 5-Me H 0 195-199 636 MeO 6-Br 7-Me 0 187-189 637 MeO 7-F H 0 221-226 638 MeO 7-F H CH2O 181-184 639 MeO H H O 230-233 640 MeO H H CH2O I 90- 195 INDEX TABLE K 0 R13\:? " 2NNNTh8$Oa X / N O r wherein R lOa is HorR10 Me Cmpd No. X R13 R9 R10a Y m.p. (°C) 641 MeO n-Bu 6-I 8-1 CH2O 166-169 642 MeO n-Pr 6-Br 8-Br CH2O 160-163 643 MeO Me 6-1 H CH20 200-204 644 MeO n-Bu 6-I 8-1 0 165-167 INDEX TABLE L R4a 4 R3 tY/z N XYYO N-N wherein R4a is H or R4 CR3 CmpdNo. X R3 R4a Y Z mg. (°C) 656 MeO 5-Cl H O 3-(3-CF3O-Ph)-1,2,4- thiadiazol-5-yl 657 MeO 5-Cl H O 3-(3,4-diCl-Ph)-1,2,4- 154-155 thiadiazol-5-yl 658 MeO 5-Cl H O 3-(3,5-diCl-Ph)-1,2,4- thiadiazol-5-yl 659 MeO 5-Cl H O 3-(3,5-diCF3-Ph)-1,2,4- thiadiazol-5-yl 660 MeO 5-Cl H O 3-(4-Br-Ph)-1,2,4- 166-168 thiadiazol-5-yl 661 MeO 5-Cl H O 3-(4-CF3-Ph)-1,2,4- thiadiazol-5-yl 662 MeO 5-Cl H O 3-(4-t-Bu-Ph)-1,2,4- 159-160 thiadiazol-5-yl 663 MeO 5-Cl H O 3-t-Bu-1,2,4-thiadiazol- 5-yl 664 MeO 3-Cl H O 3-(4-Br-Ph)-1,2,4- * thiadiazol-5-yl 665 MeO 3-Cl H O 3-(3,4-diCl-Ph)-1,2,4- * thiadiazol-5-yl 666 MeO 3-Cl H O 3-(4-CF3-Ph)-1,2,4- 120-124 thiadiazol-5-yl 667 MeO 3-Cl H O 3-(3-CF3O-Ph)-1,2,4- thiadiazol-5-yl 668 MeO 3-Cl H O 3-t-Bu- | .2,4-thiadiazol- 5-yl 669 MeO 3-Cl H O 3-(3,5-diCl-Ph)-1,2,4- 130-135 thiadiazol-5-yl 670 MeO 3-Cl H O 3-(3,5-diCF3-Ph)-1,2,4- * thiadiazol-5-yl 671 MeO 3-Cl H O 3-(4-t-Bu-Ph)-i,2,4- * thiadiazol-5-yl 672 MeO 6-CH3 H O 3-(3,5-diCl-Ph)-1,2,4- 152-1 58 thiadiazol-5-yl 673 MeO 6-CH3 H O 3-(3,4-diCl-Ph)-1,2,4- thiadiazol-5-yl 674 MeO 6-CH3 H O 3-(3-CF3-Ph)-1,2,4- 119-120 thiadiazol-5-yl 675 MeO 6-CH3 H O 3-(3,5-diF-Ph)-1,2,4- 124-126 thiadiazol-5-yl 676 MeO 6-CH3 H O 3-(3-CH3-Ph)-1,2,4- 109-111 thiadiazol-5-yl 677 MeO 6-CH3 H O 3-(3-CF3O-Ph)-1,2,4- 91-93 thiadiazol-5-yl 678 MeO 6-CH3 H O 3-(4-CH3-Ph)-1,2,4- 123-125 thiadiazol-5-yl 679 MeO 6-CH3 H O 3-(4-CF3-Ph)-1,2,4- 109-111 thiadiazol-5-yl 680 MeO 6-CH3 H O 3-(3,5-diCF3-Ph)-1,2,4- 95-98 Ex. 22 tbiadiazol-5-yl 681 MeO 6-CH3 H O 3-(2-CH3-PhO)-Ph oil- 682 MeO 6-CH3 H O 3-PhO-Ph oil* 683 MeO 6-CH3 H O 3-(2-Cl-PhO)-Ph oil* 684 MeO 6-CH3 H O 3-(2-F-PhO)-Ph oil* 685 Cl 6-CH3 H CH2O 3-(4-CF3-Ph)-1,2,4- 130-132 thiadiazol-5-yl 686 Cl 6-CH3 H bond CH2Br 120-121 687 MeO 6-CH3 H O 6-(2-CH3-PhO)-4- 135-136 pyrimidinyl 688 MeO 6-CH3 H O 3-(4-F-PhO)-Ph oil* 689 MeO 6-CH3 H O 3-(2,6-diF-PhO)-Ph oil'- 690 MeO 4-CH3O H 0 3-(4-CF3-Ph)-1,2,4- 110-1 12 thiadiazol-5-yl 691 MeO 4-CH3O H 0 3-(3,5-diCF3-Ph)-1,2,4- 107-110 thiadiazol-5-yl 692 MeO 6-CH3 H O 3-(2,6-diCl-4-pyridinyl)- oil/solid* 1,2,4-thiadiazol-5-yl 693 MeO 6-CH3 H O 3-(2,6-diCl-benzyl)- 128-129 1,2,4-thiadiazol-5-yl 694 MeO 4-CH3O H O 3-(2,6-diCl-4-pyridinyl)- 150-156 1,2,4-thiadiazol-5-yl 695 MeO 4-CH3O H O 3-(2,6-diCl-benzyl)- 113-119 1,2,4-thiadiazol-5-yl 696 Cl 6-CH3 H O CH3 132-134 697 Cl 4-CH3O H O CH3 144-146 698 MeO 6-CH3 H O 6-Cl-4-pyrimidinyl 108-110 699 MeO 6-CH3 H O 3-t-Bu-1,2,4-thiadiazol- 146-147 5-yl 700 MeO 4-CH3O H O 3-t-Bu-1,2,4-thiadiazol- oil* 5-yl 701 MeO 6-CH3 H 0 6-(3,5-diCF3-Ph)-4- 195-198 pyrimidinyl 702 MeO 4-CH3 H CH2 3-CF3-1H-pyrazol-1-yl 368** 703 MeO 6-CH3 H 0 6-(4-CF3-Ph)-4- 148-150 pyrimidinyl 704 MeO 6-CH3 H O 6-(4-CF3-Ph)-2- 128-131 pyrazinyl 705 MeO 4-CH3O H O 3-(3,5-diCl-Ph)-1,2,4- 173-176 thiadiazol-5-yl 706 MeO 6-CH3 H 0 6-(3-CF3-Ph)-2- 118-120 pyrazinyl 707 MeO 6-CH3 H O 3-F-2-NO2-Ph oil* 708 MeO 6-CH3 H 0 6-(3,5-diCF3-Ph)-2- 185-187 pyrazinyl 709 MeO 6-CH3 H O 6-Cl-2-pyrazinyl 122-124 710 Cl 6-CO2Me H bond CH2Br 168-170 711 Cl 6-CO2Me H bond CHBr2 129-131 712 MeO 4-CH3O H O 3-(3,5-diF-Ph)-1,2,4- 149-153 thiadiazol-5-yl 713 MeO 6-CH3 H O 6-(4-CO2Et-Ph)-4- 97-103 pyrimidinyl 714 MeO 6-CH3 H O 6-(4-CO2Et-Ph)-2- 158-161 pyrazinyl 715 MeO 6-CH3 H O 6-(3-CF3-Ph)-4- 125-127 pyrimidinyl 716 MeO 6-CH3 H O 6-Ph-2-pyrazinyl 137-139 717 MeO 6-CH3 H O 6-(4-Cl-Ph)-2-pyrazinyl 166-171 718 MeO 6-CH3 H O 6-(2-Br-PhO)-4- 127-129 pyrimidinyl 719 MeO 6-Et H O 3-(3,5-diCF3-Ph)-1,2,4- 136- I Ex. 23 thladiazol-5-yl 720 MeO 6-CH3S H O 3-(3,5-diCF3-Ph)-1,2,4 154-156 thiadiazol-5-yl 721 MeO 6-CH3S H O 3-(3,5-diCl-Ph)-1,2,4- 204-208 thiadiazol-5-yl 722 MeO 6-CH3S H O 3-(3,5-diF-Ph)-1,2,4- 164-166 thiadiazol-5-yl 723 MeO 6-Et H O 3-(3,5-diCl-Ph)-1,2,4- 139-142 thiadiazol-5-yl 724 MeO 6-Et H O 3-(3,5-diF-Ph)-1,2,4- 115-119 thiadiazol-5-yl 725 MeO 6-CHO H O 3-(3,5-diF-Ph)-1,2,4- 125-128 thiadiazol-5-yl 726 MeO 6-CH3 H O 3-(2-Br-PhO)-Ph oil* 727 MeO 6-Et H O 3-(4-CH3-Ph)-1,2,4- 43-55 thiadiazol-5-yl 728 MeO 6-CH3S H O 3-(4-CH3-PH)-1,2,4- 138-140 thiadiazol-5-yl 729 MeO 6-CHO H O 3-(3,5-diCl-Ph)-1,2,4- 180-185 thiadiazol-5-yl 730 MeO 6-CHO H O 3-(3,5-diCF3-Ph)-1,2,4- 144-146 thiadiazol-5-yl 731 MeO 6-CHO H O 3-(4-CH3-Ph)-1,2,4- 118-123 thiadiazol-5-yl 892 MeO 4-Br H direct bond 2-CF3-thiazolo[3,2- 177- 18 I b][1,2,4]triazol-5-yl 893 MeO 4-Me H direct bond 2-CF3-thiazolo[3,2- 180-182 b][1,2,4]triazol-5-yl 894 MeO 6-OH H O 3-(3,5-diCl-Ph)-1 ,2,4- 216-219 thiadiazol-5-yl 895 MeO 6-CH3S H O 3-t-Bu-1,2,4-thiadiazol- 146-147 5-yl 896 MeO 6-Me H O 3-(4-1-PhO)-Ph oil' 897 MeO 6-CHO H O 3-t-Bu-1,2,4-thiadiazol 105-110 5-yl 898 MeO 6-Et H O 3-t-Bu- I ,2,4-thiadiazol- 132-134 5-yl 899 MeO 6-Me H O 6-(2-F-PhO)-4- 149-152 pyrimidinyl 900 MeO 6-Me H O 4-(3-CF3-Ph)-2-thiazolyl 134-136 901 MeO 4-Br H CH2ON=C(Me) 3,5-diCl-Ph 902 MeO 6-Me H O 2-(2-F-PhO)-4- oil* pyrimidinyl 903 MeO 6-Me H O 4-(2-F-PhO)-2- oil* pyrimidinyl 904 MeO 3-Me H O 3-(3,5-diCF3-Ph)-1,2,4- 122-124 thiadiazol-5-yl 905 MeO 6-Me H OCH2 4-(2,5-diF-Ph)-3- oil* furazanyl N-oxide 906 MeO 3-Me H O 3-(3,5-diCl-Ph)-1,2,4- 62-65 thiadiazol-5-yl 907 MeO 6-Me H O 6-(2-CN-PhO)-4- 168-172 pyrimidinyl 908 MeO 6-Br H O 4-(3,5-diCF3-Ph)-5-Me- 114-117 2-thiazolyl 909 MeO 3-Me H CH2ON=C(Me) 3-Me-Ph 119-122 910 MeO 3-Me H O 3-t-Bu-1,2,4-thiadiazol- 151-153 5-yl 911 MeO 3-Me H O 3-(3-CF3-Ph)-1,2,4- 97-98 thiadiazol-5-yl 912 MeO 3-Me H O 3-(4-Br-Ph)- 1,2.4- 133-135 thiadiazol-5-yl 913 MeO 3-Me H O 3-(3-OCF3-Ph)-1,2,4- 88-90 thiadiazol-5-yl 914 MeO 6-Me H O 4-(3-CF3-Ph)-5-Me-2- gum* thiazolyl 915 MeO 5-Me H CH2ON=C(Me) 3-CF3-Ph 84-86 916 MeO 5-Me H CH2ON=C(Me) 3,5-diCI-Ph 100-102 917 MeO 3-Me H O 6-(2-Br-PhO)-4- 138-141 pyrimidinyl 918 MeO 3-Me H O 6-(2-F-PhO)-4- 153-155 pyrimidinyl 919 Cl 5-NO2 H CH2ON=C(Me) 3-CF3-Ph 920 MeO 5-Me H O 3-(3,5-diCI-Ph)- 1,2,4- 152-ISA thiadlazol-Syl 921 MeO 5-Me H O 3-t-Bu-1 2,4-thiadiazol- 1114- 11)5 5-yl 922 MeO 6-CH2=CH H O 3-(3,5-diCl-Ph)-1,2,4- 171-172 thiadiazol-Syl 923 MeO 6-Br H O 4-t-Bu-5-Me-2-thiazolyl 128-131 924 MeO 5-NO2 H CH2ON=C(Me) 3-CF3-Ph * 925 MeO 5-NO2 H CH2ON=C(Me) 3,5-diC1-Ph 926 MeO 6-Me H O 6-(2-CI-PhO)-4- 147- 149 pyrimidinyl 927 MeO 6-Me H O 6-(2-Et-PhO)-4- 127-128 pyrimidinyl 928 MeO 6-Me H O 6-PhO-4-pyrimidinyl 135-137 929 Cl 6-CO2Me H CH2ON=C(Me) 4-CF3-2-pyridinyl 116-1 17 930 MeO 6-Me H O 6-(2-OMe-PhG)-4- 1 ()7- 109 pyrimidinyl 931 MeO 6-Me 3-Me CH2ON=C(Me) 3,5-diCl-Ph 932 MeO 6-Me H O 6-(2-NO2-PhO)-4- 70-73 pyrimidinyl 933 MeO 6-Me H O 6-(2-NH2-PhO)-4- 140-1 45 pyrimidinyl 934 MeO 6-Me H O 3-CO2Me-6-CF3-2- 146-147 pyridinyl 935 MeO 6-Br H O 4-(3-CF30-Ph)-5-Me-2- 108-112 thiazolyl 936 MeO 6-BrCH2 H CH2ON=C(Me) 4-CF3-2-pyridinyl oil 937 MeO 6-Me H CH2ON=C(Me) 4-Me-Ph oil- 938 MeO 6-CHO H O 3-(4-CF3-Ph)-1,2,4- 112-114 thiadiazol-5-yl 939 MeO 6-CHO H O 3-(2,6-CI-4-pyridinyl)- 155-157 1,2,4-thiadiazol-5-yl 940 MeO 6-Me H O 4-t-Bu-5-Br-2-thiazolyl 184-187 941 MeO 6-Me H O 4-t-Bu-2-thiazolyl 79-81 942 MeO 6-Me H O 4-t-Bu-5-Me-2-thiazolyl 157-160 943 MeO 6-SiMe3 H O 4-(3-CF30-Ph)- * 5-SiMe3-2-thiazolyl 944 MeO 6-Me H O 4-(3-CF3-Ph)-5-Br-2- 100-101 thiazolyl 945 MeO 6-n-C5H11 H O 4-t-Bu-5-Me-2-thiazolyl oil* 946 MeO 6-n-C5H11 H O 4-(3-CF3-Ph)-5-Me-2- oil* thiazolyl 947 Cl 5-Cl H CH2ON=C(Me) 3-CF3-Ph oil* 948 MeO 5-Cl H CH2ON=C(Me) 3-CF3-Ph 121-123 949 Cl 6-Me H CH2ON=C(Me) 3-CF3-Ph oil 950 MeO 6-Me H CH2ON=C(Me) 3-CF3-Ph oil' 951 Cl 4-OMe H CH2ON=C(Me) 3-CF3-Ph oil'- 952 MeO 4-OMe H CH2ON=C(Me) 3-CF3-Ph 115-117 953 MeO 4-Me H CH2ON=C(Me) 3-CF3-Ph oil 954 MeO 3-Me H CH2ON=C(Me) 3-CF3-Ph oil 955 MeO 6-Me H CH2ON=C(Me) 3,5-diCl-Ph 956 MeO 6-OMe H CH2ON=C(Me) 3,5-diCl-Ph foam* 957 MeO 6-OMe H CH2ON=C(Me) 3-CF3-Ph foams; 958 MeO 3-Me H CH2ON=C(Me) 3,5-diCI-Ph 159-161 959 MeO 6-F H CH2ON=C(Me) 3-CF3-Ph oil* 960 MeO 6-F H CH2ON=C(Me) 3,5-diCI-Ph 120-121 961 MeO 6-Me H CH2ON=C(Me) 3,5-diBr-Ph 163-164 962 MeO 6-Me H CH2ON=C(Me) 3-CF30-Ph oil* 963 MeO 6-Me H CH2ON=C(Me) 3,4-diCI-Ph 109-110 964 MeO 6-Me H CH2ON=C(Me) 4-CF3-2-pyridinyl oil 965 MeO 6-Me H CH2ON=C(Me) 2-naphthalenyl glue* 966 MeO 3-F H CH2ON=C(Me) 3-CF3-Ph solid' 967 MeO 4-Me 6-Me CH2ON=C(Me) 3-CF3-Ph oil* 968 Cl 6-CO2Me H CH2ON=C(Me) 3-CF3-Ph 109-111 969 MeO 4-Me 6-Me CH2ON=C(Me) 3,5-diCl-Ph 116-I 19 970 MeO 4-Br H CH2ON=C(Me) 3-CF3-Ph 126-128 971 MeO 4-Me3SiC#C H CH2ON=C(Me) 3-CF3-Ph oil 972 MeO 4-HC-C H CH2ON=C(Me) 3-CF3-Ph gum* 973 a MeO 6-Br H O 4-(3-CF3-Ph)-5-Me-2- 125-130 thiazolyl 974 MeO 6-CHO H O CH3OCH2 116-117 975 MeO 6-CH2Br H O CH3OCH2 144-145 976 MeO 6-Me H O 3-CF3-PhOCH2 oil* 977 MeO 6-Me H O 3-CF3-Ph 95-96 978 MeO 6-Me H O 4-CI-Ph 87-89 a Compound contains 20% by weight of 4-[2-chloro-6-[[5-methyl-4-[3- (trifluoromethyl)phenyl]-2-thiazolyl]oxy]phenyl]-2,4-dihydro -5-methoxy-2-methyl- 3H- 1 ,2,4-triazol-3-one.

* See Index Table M for H NMR data.

** Protonated parent molecular ion (m/e) measured by mass spectrometry using atmospheric pressure chemical ionization in the positive ion mode (APCI+). The ion shown corresponds to the M+H+ ion calculated from the integral values of the atomic weights of the most abundant isotope of each element present.

INDEX TABLE M Cmpd No. 1H NMR Data (CDC13 solution unless indicated otherwise)a 2 # 7.51(dd,1H), 7.27(dt,1H), 7.17(m,2H), 6.97(dd,1H), 6.6(m,3H), 3.92(s,3H), 3.74 (s,3H), 3.33 (s,3H).

3 5 7.32(m,7H), 6.99(m,2H), 5.08(s,2H), 3.84(s,3H), 3.42(s,3H).

4 # 7.25(m,4H), 3.98(s,3H), 3.45(s,3H), 2.30(s,3H).

5 # 7.61(d,1H), 7.35(m,3H), 7.11(m,3H), 6.84(t,2H), 5.12(s,2H), 3.96(s,3H), 3.415(s,3H), 2.24(s,3H).

14 # 7.65(d,1H), 7.45(m,2H), 7.23(m,1H), 7.10(m,2H), 6.82(t,1H), 6.78(d,lH), 5.08(s,2H), 4.29(m,2R), 3.41 (s,3H), 2.24(s,3H). 1.31 (t.3H 17 # 7.6-7.45(m,5H), 7.20(m,1H), 7.14(d,2H), 5.27(d,1H), 5.16(d,1H), 3.46(s,3H), 2.34(s,3H), 2.16(s,3H).

19 # 7.6(d,1H), 7.5(m,3H), 7.4(t,1H), 7.25(m,1H), 7.15(d,2H), 5.26(d,1H), 5.20(d,1H), 3.48(s,3H), 2.41(s,3H), 2.43(s,3H), 2.18(s,3H).

20 # 7.62(m,2H), 7.5(m,2H), 7.35-7.2(m,4H), 5.25(d,1H), 5.15(d,1H), 3.48(s,3H), 3.02(m,2H), 2.85(m,2H).

21 # 7.42(m,2H), 7.10(m,1H), 7.06(m,3H), 6.99(t,1H), 6.68(d.2H), 3.37(s,3H), 2.51(s,3H).

23 # 8.01(s,1H), 7.61(d,1H), 7.52(m,4H), 7.35(m,3H), 7.25(d,1H), 5.23(d,1H), 5.15(d,1H), 3.49(s,3H).

24 # 7.6(m,2H), 7.5-7.4(m,3H), 7.3-7.2(m,3H), 5.24(d,1H), 5.20(d,1H), 3.48(s,3H), 2.40(s,3H).

25 # 7.6-7.4(m,4H), 7.35(m,2H), 7.2(m,2H), 7.0(d,2H), 6.6(m,3H), 5.04(d,1H), 5.00(d,lH), 3.45(s,3H).

26 # 7.6(d,1H), 7.45(m,2H), 7.33(t,2H), 7.19(m,2H), 7.10(t,1H), 7.01(d,2H) 6.6(m,3H), 5.03(m,2H), 3.87(s,3H), 3.39(s,3H).

35 # 7.6-7.4(m,7H), 7.23(d,1H), 5.28(d,1H), 5.17(d,1H), 3.46(s,3H), 2.14(s,3H).

36 # 7.80(d,2H), 7.65-7.45(m,6H), 7.36(d,2H), 7.30(m,1H), 7.25(m,1H), 7.10(t,1H), 5.15(d,1H), 5.10(d,1H), 3.45(s,2H).

38 # 7.77(d,2H), 7.6(m,2H), 7.47(m,4H), 7.35(m,3H), 7.25(m,1H), 7.10(m,lH), 5. 13(d,1H), 5.12(d,lH), 3.89(s,3H), 3.38(s,3H).

39 # 8.03(s,1H), 7.70(d,1H), 7.53(m,2H), 7.35-7.25(m,5H), 5.06(s,2H), 3.46(s,3H).

40 # 7.6-7.5(m,3H), 7.24(m,1H), 7.13(s,1H), 7.02(d,1H), 6.78(d,1H), 5.96(s,2H), 5.26(d,1H), 5.14(d,1H), 3.48(s,3H), 2.13(s,3H).

41 # 8.04(s,1H), 7.8(m,1H), 7.45(m,2H)7.35-7.25(m,5H), 5.10(s,2H), 3.86(s,3H), 3.41(s,3H).

42 6 7.58(m,lH), 7.43(m,2H), 7.25(m,1H), 7.15(m,1H), 7.02(d, IH), 6.76(d,1H), 5.96(s,2H), 5.22(d,1H), 5.18(d,1H)3.89(s,3H), 3.42(s,3H), 2.15(s,3H).

43 5 8.40(s,lH), 7.6(m,lH), 7.5-7.4(m,5H), 7.3(d,1H) 7.18(m,2H), 6.38(s,1H), 3.45(s,3H).

45 # 7.55(d,1H), 7.40(m,3H), 7.20(m,4H), 5.21(d,1H), 3.87(s,3H), 3.42(s,3H), 2.24(s,3H).

47 # 7.67-7.2(m,9H), 5.4-5.2(m,2H), 3.87,3.83(s,3H), 3.41,3.40(s,3H).

48 # 7.6(m,3H), 7.44(m,2H), 7.35(m,3H), 7.25(m,1H), 5.26(d,1H), 5.22(d,1H), 3.88(s,3H), 3.49(s,3H), 2.20(s,3H).

49 # 7.5(d,1H), 7.40(m,4H), 7.23(m,2H), 7.18(d,1H), 5.26(d,1H), 5.21(d,1H), 3.88(s,3H)3.41(s,3H), 2.36(s,3H), 2.19(s,3H).

50 # 7.56(m,3H), 7.45(m,2H), 7.25(m,1H), 6.86(d,2H), 5.24(d,1H), 5.19(d,1H), 3.88(s,3H), 3.81(s,3H), 3.41(s,3H), 2.17(s,3H).

51 # 7.5(m,2H), 7.45(m,3H), 7.3(m,3H), 5.27(d,1H), 5.22(d,1H),3.89(s,3H).

52 # 8.02,8.01(s,1H), 7.8,7.7(m,1H), 7.45(m,2H), 7.35(m,4H), 7.25(m,2H), 5.25(m,1H), 3.88,3.74(s,3H), 3.45,3.39(s,3H), 1.62-1.56(m,3H).

53 # 8.04(s,1H), 7.81(m,1H), 7.45(m,2H), 7.38-7.18(m,5H), 5.18(s,2H), 3.86(s,3H), 3.42(s,3H), 2.38(s,3H).

54 5 7.35(m,4H), 7.20(m,2H). 7.05(d,2H), 6.95(d,1H), 3.46(s,3H).

55 # 7.6-7.45(m,3H), 7.2(m,1H), 4.67(d,1H), 4.48(d,1H), 3.56(s,3H).

56 5 7.5(m,lH), 7.44(m,2H), 7.22(m,1H), 4.60(d, 1H), 4.36(d,1H), 3.96(s,3H), 3.47(s,3H).

60 # 7.72(d,2H), 7.58(d,3H), 7.50(m,2H), 7.26(m,1H), 5.30(d,1H), 5.24(d,1H), 3.48(s,3H), 2.42(s,3H), 2.21(s,3H).

61 # 7.70(m,2H), 7.60(m,2H), 7.43(m,3H), 7.23(m,1H), 5.30(d,1H), 5.25(d,1H), 3.85(s,3H), 3.41(s,3H).

62 5 8.40(s,lH), 7.70(m,2H), 7.6-7.3(m,6H), 6.59(s,1H), 3.80(s,3H), 339(s,3H).

64 # 8.40(s,1H), 7.5-7.2(m,7H), 7.02(,1H), 6.33(s,1H)3.78(s,3H), 3.36(s,3H), 2.18(s,3H).

65 5 8.42(s,lH), 7.55-7.26(m,7H), 7.16(d,2H), 6.36(s,1H), 3.79(s,3H)3.36(s,3H).

69 # 7.6-7.3(m,7H), 7.25(m,1H), 5.24(d,1H), 5.21(d,1H)3.89(s,3H), 3.41(s,3H), 2.18(s,3H), 1.31(s,9H).

70 # 7.60(d,1H), 7.45-7.38(m,3H), 7.35-7.20(m,2H), 7.11(d,1H), 5.74(d,1H).

5.21(d,1H), 3.88(s,3H), 3.41(s,3H), 2.27(s,3H), 2.26(s,3H), 2.18(s,3H).

75 # 8.56(s,1H), 7.58(m,1H), 7.40(m,3H), 6.99(s,1H), 3.43(s,3H).

76 # 7.66(d,2H), 7.58(m,5H), 7.5-7.3(m,5H), 7.25(m,1H), 5.28(d,1H), 5.24(d,1H), 3.90(s,3H), 3.47(s,3H), 2.23(s,3H).

77 5 7.68(d,lH), 7.6-7.5(m,2H), 7.25(m,1H), 7.00(d,lH), 6.68(d,lH), 6.61(s,1H), 5.05(d,1H), 5.00(d,1H), 3.49(s,3H), 2.29(s,3H), 2.16(s,3H), 82 # 8.02(s,2H), 7.82(s,1H), 7.6-7.45(m,3H), 7.25(m,1H), 5.33(d,1H), 5.21(d,lH), 3.50(s,3H), 2.23(s,3H).

84 # 7.6(d,1H), 7.5-7.4(m,2H), 7.4-7.2(m,5H) ,5.20(d,2H), 3.89(s,3H).

3.40(s,3H), 2.18(m,1H), 0.90(m,2H), 0.60(m,2H).

86 Two isomers: 5 7.75-7.40(m,8H), [5.29(s) and 5.22(m)](2H), [3.58(s) and 3.55(s)](3H), [2.88(s) and 2.83(s)](3H), [2.23(s) and 2.17(s)l(3H).

88 # 7.60(m,2H), 7.40(m,4H), 7.26(m,2H), 5.25(d,1H), 5.22(d,1H), 3.88(s,3H), 3.40(s,3H), 2.20(s,3H), 1.33(s,9H).

89 # 7.80(s,1H), 7.58(m,5H), 7.40(m,6H), 7.25(m,1H), 5.25(m,2H), 3.87(s,3H), 3.39(s.3H), 2.25(s,3H).

90 # 7.58(d,1H), 7.42(m,2H), 7.24(m,2H), 7.17(m,2H), 6.85(d,1H), 5.22(m,2H), 4.58(m,1H), 3.89(s,3H), 3.41(s,3H), 2.17(s,3H), 1.33(d,6H).

94 # 7.67(s,1H), 7.60-7.45(m,3H), 7.41(s,2H), 7.22(m,1H), 5.30(d,1H), 5.1 6(d, lH), 3.49(s,3H), 2.14(s,3H).

96 5 7.80(m,2H), 7.58(m,2H), 7.50(m,3H), 7.25(m,lH), 5.28(d,1H), 5.25(d,1H), 3.89(s,3H), 3.40(s,3H), 2.22(s,3H).

99 # 7.82(s,1H), 7.79(d,1H), 7.58(m,2H), 7.45(m,3H), 7.25(m,1H), 5.22(m,2H), 3.89(s,3H), 3.41(s,3H), 2.77(q,2H), 1.10(t,3H).

100 # 8.45(s,1H), 8.20(m,1H), 7.95(d,1H), 7.6-7.4(m,4H), 7.25(m,1H).

5.30(d,1H), 5.26(d,1H), 3.90(s,3H), 3.41(s,3H), 2.24(s,3H).

110 # 7.60(d,1H), 7.45(m,2H), 7.25(m,1H), 7.20(s,2H), 7.00(s,1H), 5.25(d,1H), 5,21(d,1H), 3.88(s,3H), 3.41(s,3H), 2.32(s,6H), 2.18(s,3H).

111 # 7.8(m,1H), 7.75(m,1H), 7.6-7.4(m,5H), 7.2(m,1H), 5.33(d,1H), 5.17(d,1H), 3.45(s,3H), 2.18(s,3H).

112 Major Isomer: # 7.6-7.4(m,3H), 7.34-7.20(m,5H), 5.24(d,1H), 5.14(d,1H), 3.46(s,3H), 2.1 0(m, lH), 0.90(m,2H), 0.55(m,2H).

113 # 7.89(s,1H), 7.80(d,1H), 7.60(m,2H), 7.43(m,3H), 7.25(m,1H), 5.28(d,1H), 5.24(d,lH), 3.90(s,3H), 3.42(s,3H), 2.1 9(s,3H).

114 # 8.6(d,1H), 8.0(d,1H), 7.6(m,2H), 7.5(m,3H), 7.2(m,1H), 5.48(d,1H).

4.6(d,1H), 3.56(s,3H), 3.4(s,3H).

115 # 7.64(s,1H), 7.58-7.42(m,4H), 7.30(m,1H), 7.25(m,1H), 5.29(d,1H).

5.24(d,lH), 3.90(s,3H), 3.41(s,3H), 2.19(s,3H).

121 # 7.6-7.4(m,5H), 7.36(t,1H), 7.20(m,2H), 5.30(d,1H), 5.18(d,1H), 3.47(s,3H). 2.17(s,3H).

123 # 7.72(d,2H), 7.58(d,2H), 7.51(m,1H), 7.34(m,3H), 5.31(s,2H), 3.94(s,3H), 3.43(s,3H), 2.24(s,3H).

125 # 7.62(m,1H), 7.49(m,2H), 7.32(m,5H), 5.28(s,2H), 3.95(s,3H), 3.44(s,3H), 2.21(s,3H).

126 8 7.77(t,1H), 7.49(m,3H), 7.34(m,3H), 7.22(m,1H), 5.28(s,2H), 3.94(s,3H), 3.44(s,3H), 2.2(s,3H).

127 # 7.53(m,3H), 7.32(m,5H), 5.27(s,2H), 3.93(s,3H), 3.43(s,3H), 2.20(s,3H).

128 # 7.48(m,5H), 7.33(m,3H), 5.27(s,2H), 3.93(s,3H), 3.42(s,3H), 2.2(s,3H).

129 # 7.59(m,2H), 7.52(m,1H), 7.34(m,3H), 7.02(m,2H), 5.27(s,2H).

3.94(s,3H), 3.43(s,3H), 2.22(s,3H).

130 8 7.56(m,3H), 7.33(m,3H), 6.86(m,2H), 5.25(s,2H), 3.93(s.3H).

3.81(s,3H), 2.43(s,3H), 2.21(s,3H).

131 # 7.92(m,1H), 7.84(d,1H), 7.6(m,1H), 7.47(m,2H), 7.33(m,3H), 5.30(s,2H), 3.98(s,3H), 3.45(s,3H), 2.23(s,3H).

132 # 7.73(d,2H), 7.62(d,2H), 7.50(m,1H), 7.35(m,3H), 5.31(s,2H), 3.96(s,3H), 3.44(s,3H), 2.23(s,3H).

133 # 7.5(m,3H), 7.33(m,3H), 7.14(d,2H), 5.26(s,2H), 3.92(s,3H), 3.43(s,3H), 2.34(s,3H), 2.21(s,3H).

134 # 7.51(m,2H), 7.34(m,5H), 5.27(s,2H), 3.94(s,3H), 3.43(s,3H), 2.37(s,3H), 2.2(s,3H).

135 8 7.51(m,lH), 7.33(m,3H), 7.18(d,lH), 7.06(m,1R), 6.76(d,1H), 5.95(s,2H), 5.24(s,2H), 3.94(s,3H), 3.43(s,3H), 2.18(s,3H).

136 # 7.53(m,1H), 7.40(s,1H), 7.34(m,4H), 7.1(d,1H), 5.26(s,2H), 3.93(s,3H), 3.43(s,3H), 2.26(s,3H), 2.25(s,3H), 2.21(s,3H).

137 5 7.72(d,1H), 7.44(m,3H), 7.33(m,3H), 5.28(s,2H), 3.96(s,3H), 3.44(s,3H), 2.19(s,3H).

138 8 7.71(m,2H), 7.58(m,5H), 7.44(m,2H), 7.34(m,4H), 5.3(s,2H), 3.93(s,3H), 3.43(s,3H), 2.26(s,3H).

139 7.63(m,1H), 7.54(m,1H), 7.37(m,3H), 7.3(m,3H), 5.28(s,2H), 3.92(s,3H), 3.43(s,3H), 2.24(s,3H), 1.33(s,9H).

140 # 8.07(s,2H), 7.83(s,1H), 7.51(m,1H), 7.35(m,3H), 5.35(s,2H), 3.96(s,3H), 3.44(s,3H), 2.27(s,3H).

141 # 7.53(d,1H), 7.34(m,3H), 7.24(m,1H), 7.18(m,2H), 6.89(m,1H), 5.28(s,2H), 3.94(s,3H), 3.82(s,3H), 3.44(s,3H), 2.22(s,3H).

142 5 7.83(t,1H), 7.58(m,5H), 7.43(m,3H), 7.34(m.4H), 5.3(s,2H), 3.91 (s,3H), 3.42(s,3H), 2.28(s,3H).

143 # 7.56(m,3H), 7.33(m,5H), 7.13(m,1H), 6.99(m,4H), 5.26(s,2H), 3.94(s,3H), 3.43(s,3H), 2.22(s,3H).

144 # 8.57(d,1H),7.85(d,1H), 7.65(t,1H), 7.53(d,1H), 7.3-7.4(m,3H), 7.22(t,1H), 5.32(s,2H), 3.95(s,3H), 3.44(s,3H), 2.3(s,3H), 145 # 7.54(m,1H), 7.32(m,3H), 7.2(t,1H), 6.95(m,2H), 6.73(m,1H), 5.27(s,2H), 3.91(s,3H), 3.43(s,3H), 2.95(s,6H), 2.22(s,3H), 146 # 7.52(m,3H), 7.34(m,4H), 7.18(m,1H), 5.29(s,2H), 3.94(s,3H); 3.43(s,3H), 2.22(s,3H).

147 # 7.54(m,3H), 7.33(m,3H), 6.96(m,2H), 6.88(m,4H), 5.25(s,2H), 3.93(s,3H), 3.8(s,3H), 3.43(s,3H), 2.21(s,3H).

153 # 7.5(m,1H), 7.34(m,7H), 7.26(m,1H), 7.11(m,1H), 6.97(m,2H), 5.25(s,2H), 3.92(s,3H), 3.42(s,3H), 2.2(s,3H) 154 # 7.53(m,1H), 7.33(m,3H), 7.24(m,1H), 7.15(m,2H), 6.86(m,1H), 5.27(s,2H), 4.57(m,1H), 3.92(s,3H), 3.43(s,3H), 2.21(s,3H), 1.33(d,6H) 155 # 7.49(m,3H), 7.34(m,4H), 5.29(s,2H), 3.95(s,3H), 3.44(s,3H), 2.18(s,3H).

156 # 7.87(d,1H), 7.78(d,1H), 7.6(m,1H), 7.5(m,2H), 7.33(m,3H), 5.3(s,2H), 3.95(s,3H), 3.44(s,3H), 2.77(q,2R), 1.12(t,3H).

157 # 7.47-7.45(m,1H), 7.39-7.27(m,3H), 5.09(s,2H), 3.95(s,3H), 3.43(s,3H), 1.79-1.68(m,9H), 1.31-1.20(m,5H).

158 5 7.48-7.28(m,4H), 5.10 and 5.08(2s,2H total), 3.95 and 3.81(2s,2H total), 3.44 and 3.35(2s,3H total), 1.85-1.79(m,8H), 1.26-0.84(m,14H).

159 # 7.82(d,2H), 7.77(d,1H), 7.58(m,5H), 7.45(t,1H), 7.34(m,3H), 5.31(s,2H), 3.92(s,3H), 3.42(s,3H)2.29(s,3H).

160 # 7.48(m,3H), 7.33(m,6H), 7.23(m,1H), 7.14(d,1H), 7.14(d,1H), 7.00(d,1H), 5.26(s,2H), 3.93(s,3H), 3.42(s,3H), 2.2(s,3H).

161 5 7.66(s,1H), 7.51(m,2H), 7.33(m,4H), 5.32(s,2H), 3.96(s,3H), 3.44(s,3H), 2.22(s,3H).

162 # 7.53(d,1H), 7.35(m,3H), 7.24(m,2H), 6.98(s,1H), 5.27(s,2H), 3.92(s,3H), 3.43(s,3H), 2.31(s,6H), 2.21(s,3H).

164 # 7.45-7.55(d,1H), 7.30-7.35(m,3H), 6.45(d,1H), 6.05(d,1H), 5.26(s,2H).

3.96(s,3H), 3.43(s,3H), 2.33(s,3R), 2.13(s,3H).

165 # 7.52(d,1H), 7.45(s,1H), 7.37-7.31(m,3H), 6.92(s,1H), 5.30(s,2H).

3.95(s,3H), 3.44(s,3H), 2.50(s,3H), 2.32(s,3H), 2.30(s.3H).

166 # 7.53(m,3H), 7.34(m,3H), 7.18(d,2H), 5.26(s,2H), 3.93(s,3H), 3.43(s,3H), 2.5(br,1H), 2.22(s,3H), 1.78(m,6H), 1.41(m,4H).

168 # 8.57(s,1H), 8.40-8.50(m,2H), 7.43-7.50(m,4H), 7.35-7.40(m,3H), 5.30(s,2H), 3.96(s,3H), 3.44(m,3H), 2.55(s,3H), 2.24(s,3H).

169 # 8.45(t,1H), 7.80(t,1H), 7.57(s,1H), 7.33-7.50(m,6H), 5.35(s,2H), 3.89(s,3H), 3.43(s,3H), 2.33(s,3H).

171 5 7.69(d,2H), 7.62(m,1H), 7.49(m,1H), 7.34(m,3H), 5.29(s,2H), 3.96(s,3H), 3.45(s,3H), 2.17(s,3H).

172 # 7.86(m,2H), 7.5(m,1H), 7.33(m,3H), 7.18(m,1H), 5.29(s,2H), 3.96(s,3H), 3.44(s,3H), 2.23(s,3H).

173 57.47(d,lH), 7.30-7.39(m,3H), 7.19(s,1H), 6.79(s,1H), 5.30(s,2H).

3.97(s,3H), 3.91(s,3H), 3.45(s,3H), 2.15(s,3H).

176 Major isomer: # 7.69(t,1H), 7.57(d,2H), 7.35(m,4H), 5.17(s,2H), 4.03(s,3H), 3.97(s,3H), 3.45(s,3H). Minor isomer: # 7.7(t,1H), 7.6(d,2H), 7.50(m,4H), 5.11(s,2H), 3.88(s,3H), 3.73(s,3H), 3.43(s,3H).

177 # 7.53(m,1H), 7.45(m1H), 7.42(m,1H), 7.34(m,3H), 7.24(m,1H), 7.17(m1H), 5.28(s,2H), 3.91(s,3H), 3.42(s,3H), 2.65(q,2H), 2.23(s,3H), 1.23(t,3H).

178 # 7.60-7.30(m,7H), 5.29(s,2H), 3.95(s,3H), 3.94(s,3H), 3.44(s,3H), 2.30(s,3H).

179 # 2.34(s,3H), 3.43(s,3H), 3.93(s,3H), 5.33(s,2H), 7.35(m,3H), 7.47(m,2H), 7.56(t,1H), 7.83(m,4H), 7.97(d,1H).

180 5 2.34(s,3H), 2.51(s,3H), 3.44(d,3H), 3.94(d,3H), 5.32(s,2H), 7.35(m,4H), 7.565(m,2H), 7.71(m,2H), 7.83(m,lH), 7.93(s,1H).

181 # 2.33(s,3H), 3.43(s,3H), 3.91(s,3H), 3.93(s,3H), 5.32(s,2H), 7.13(m,2H), 7.35(m,3H), 7.56(m,1H), 7.70(m,1H), 7.75(m, 1 H), 7.83(m,1H), 7.905(s,1H).

182 8 2.33(s,3H), 3.44(s,3H), 3.95(s,3H), 5.33(s,2H), 7.35(m,3H), 7.55(m,2H), 7.70(t,2H), 7.925(m,3H).

183 # 1.78(m,4H), 2.21(s,3H), 2.75(d,4H), 3.43(s,3H), 3.92(s,3H), 5.26(s,2H), 7.01(m,1H), 7.20(m,1H), 7.32(m,5H), 7.52(m,1H).

189 # 7.63(m,3H), 7.40(m,5H), 7.20(m,1H), 5.12(AB q, 2R), 3.94(d,3H), 3.875(s,3H), 3.41(s,3H).

190 # 7.75(m,1H), 7.48(m,5H), 7.22(m,2H), 5.24(q,2H), 3.89(s,3H), 3.41(s,3H), 2.16(s,3H).

192 8 8.05(d,1H), 7.6-7.9(m,lH), 7.6(s,1H), 7.4-7.6(m,5H), 7.2-7.3(1 H).

5.3(m,lH), 3.7-3.9(d,3H), 3.45(m,3H), 1.6(m,3H).

193 # 3.47(s,3H), 6.7-6.8(m,3H), 7.0(m,3H), 7.12(t,3H), 7.2-7.3(m,2H), 7.3-7.5(m,4H).

194 # 3.38(s,3H), 3.83(s,3H), 6.7-6.8(m,3H), 7.0-7.1(m,3H), 7.1-7.2(m,3H), 7.3-7.4(m,4H).

198 8 7.94(t, 1 H), 7.66(m,1H), 7.54(m,2H), 7.43(m,2H), 7.23(d,1H), 7.06(t,1H), 5.24(q,2R), 3.88(s,3H), 3.41(s,3H), 2.14(s,3H).

199 # 7.55(m,1H), 7.51(m,2H), 7.46(m,2H), 7.25(m,1H), 5.14(q,2H), 4.08(s,3H), 3.915(s,3H), 3.435(s,3H).

200 # 7.92(s,1H), 7.85(d,1H), 7.60(m,2H), 7.45(m,3H), 7.24(m,1H), 5.14(q,2H), 4.03(s,3H), 3.88(s,3H), 3.41(s,3H).

201 # 7.2-7.5(m,4H), 6.9-7.3(t,1H), 3.42(s,3H), 2.22(s,3H).

203 # 7.55(m,5H), 7.25(d,1H), 5.12(q,2H), 4.07(s,3H), 3.53(s,3H).

204 # 7.85(s,1H), 7.75(d,1H), 7.4-7.7(m,5H), 7.3(d,1H), 7.05(t,1H), 5.23(m,2H), 3.34(s,3H), 2.19(s,3H).

205 # 7.45-7.65(m,5H), 7.33(s,1H), 7.26(d,1H), 5.1-5.4(m,2H), 3.5(s,3H).

2.13(s,3H).

207 # 7.60(d,1H), 7.50-7.30(m,4H), 7.25(m,2H), 5.23(d,1H), 5.20(d,1H), 3.89(s,3H), 3.41(s,3H), 2.18(s,3H), 1.68(s,4H), 1.26(m,12H).

209 # 7.58(m,1H), 7.37(m,2H), 7.23(m,3H), 6.60(d,2H), 4.23(s,2H), 3.86(s,3H), 3.41(s,3H).

210 (for the EIZ mixture) # 7.66 and 7.21 (2s,lH total), 7.25-7.54 (m,4H total), 3.93 and 3.91 (2s,3H total), 3.44 (s,3H), 1.54 and 1.25 (2s,9H total).

211 # 8.18(s,1H), 7.98(m,1H), 7.82(m,1H), 7.50(m,4H), 7.30(d,1H), 5.59(d,1H), 5.46(d,1H), 3.39(s,3H), 3.41(s,3H).

212 8 7.56(m,2H), 7.44(m,3H), 7.25(m,2H), 5.26(AB q, 2H), 3.9(s,3H), 3.41(s,3H), 2.1(s,3H).

214 # 7.68(d,1H), 7.6(m,1H), 7.48(m,4H), 7.28(m,1H), 5.41(AB q,2H), 3.91(s,3H), 3.38(s,3H), 3.20(s,3H).

215 8 7.6(d,1H), 7.3-7.5(m,4H), 7.2(d,1H), 6.95(s,1H), 6.9(d,1H), 4.27(s,2H), 3.86(s,3H), 3.41(s,3H), 1.95(s,3H).

217 # 7.65(d,1H), 7.6-7.1(m,6H), 5.15(m,2H), 3.95(m,1H), 3.45(s,3H), 2.6(d,3H), 2.2(s,3H), 1.65(s,4H), 1.25(s,12H).

220 # 3.6(s,3H), 6.8(m,3H), 7.0-7.1(m,3H), 7.1-7.2(m,2H), 7.3(m,1H), 7.35(m,3H), 7.45(m,1H).

221 [in Me2SO-d6]: # 1.95(s,3H), 2.0(s,3H), 3.75(d,2H), 3.85(s,3H).

6.55(m,2H), 7.05(m,1H), 7.4-7.5(m,3H), 9.05(s,1H).

222 # 7.76(s,1H, 7.60(m,1H), 7.54(m,1H), 7.36(d,1H), 7.32(d,1H), 6.94(d,1R), 5.29(s,2H), 3.89(s,3H), 3.41(s,3H), 2.21(s,3H), 0.28(s,9H).

231 # 7.67(m,1H), 7.52(m,3H), 7.36(m,4H), 5.35(s,2H), 3.77(s,3H), 3.44(s,3H), 2.20(s,3H), 0.27(s,9H).

236 # 8.68(d,1H), 7.80(s,1H), 7.75(d,1H), 7.60(m,2H), 7.43(m,2H), 5.54(d,1H), 5.40(d,1H), 3.82(s,3H), 3.35(s,3H), 2.17(s,3H).

237 # 7.84(s,1H), 7.77(d,J=8Hz, 1H), 7.58(m,2H), 7.45(m,3H), 7.26(m,1H), 5.31(d,J=13Hz, 1H), 5.22(d,J=13Hz, 1H), 3.89(s,3H), 3.81(m,2H), 2.21 (s,3H), 1.33(t,J=7Hz, 3H).

238 # 1.6-1.8(m,13H), 2.0-2.1 (m,SH), 3.44 (s,3H), 3.94 (s,3H). 5.09 (s,2H), 7.32 (m,3H), 7.48 (m,lH).

240 87.39 (m,lH), 7.33 (d,2H), 7.26 (m,1H), 6.99 (m,2H), 6.88 (m.2H).

5.01 (s,2H), 3.84 (s,3H), 3.81 (s,3H), 3.41 (s,3H).

243 # 7.43 (m,3H), 7.28 (m,1H), 7.22 (m,2H), 7.15 (m,1H), 7.04 (m,1H).

5.12 (q,2H) 4.51 (s,2H), 3.89 (s,3H), 3.43 (s,3H), 1.91 (s,3H).

244 # 7.45 (m,3H), 7.23 (m,lH), 5.06 (q,2H), 4.05 (s.2H), 3.93 (s,3H), 3.895 (s,3H), 3.44(s,3H), 1.94 (s,3H).

246 # 7.58 (m,lH), 7.41 (m,4H), 7.26 (m,3H), 5.12 (q,2H), 4.08 (d,2H), 3.92 (s,3H), 3.44 (s,3H), 1.96 (s,3H).

247 #7.57 (m,lH), 7.44 (m,3H), 7.32 (d,2H), 7.24 (m,lH), 5.27 (q,2H), 3.9 (s,3H), 3.415 (s,3H), 2.12 (s,3H).

249 # 7.44(m,3H), 7.23 (m,1H), 6.96 (m,1H), 6.81 (m,2H), 5.12 (q,2H).

4.44 (s,2H), 3.9 (s,3H), 3.43 (s,3H), 1.89 (s,3H).

250 # 7.6 (d,lH), 7.15-7.5 (m,SH), 6.95 (s,lH), 6.85 (d,lH), 4.24 (s,2H), 3.85 (s,3H), 3.41 (s,3H), 2.3 (m,2H), 1.05 (t,3H).

252 # 7.45 (m,4H), 7.25 (m,2H), 5.30 and 5.10 (2m,2H total), 3.91 and 3.88 (2s,3H total), 3.42 and 3.41 (2s,3H total), 2.14 and 2.11 (2s,3H total).

254 # 7.56 (m,3H), 7.45 (m,2H), 7.35 (t,lH), 7.25 (m,1H), 5.12 (q,2H), 4.01 (s,3H), 3.89 (s,3H), 3.43 (s,3H).

255 # 3.47 (s,3H), 3.77 (s,3H), 6.61 (m,2H), 6.70 (m,lH), 7.01 (dd,1H,J=1.2,8.2), 7.2-7.3 (m,2H), 7.34-7.42 (m,2H).

259 # 1.80(d,6H), 3.52 (s,3H), 5.01 (q,2H), 7.26 (m,lH), 7.52 (m,3H).

262 # 7.85 (d,lH), 7.8 (m,lH), 7.55 (d,lH), 7.45 (m,2H), 7.25 (1H).

7.2 (t,lH), 5.25 (m,2H), 3.9 (s,3H), 3.4 (s,3H), 2.19 (s,3H).

265 # 7.84 (m,3H), 7.64 (d,2H), 7.6-7.55 (m,1H), 7.5-7.4 (m,2H), 3.88 (s,3H), 3.43 (s,3H).

273 # 8.11 (d,2H), 7.85 (d,lH), 7.77 (d,2H), 7.6-7.5 (m,lH), 7.5-7.4 (m,2H), 3.89 (s,3H), 3.43 (s,3H).

275 # 3.38 (s,3H), 3.85 (s,3H), 6.7-6.9 (m,3H), 6.95 (m,1H), 7.1 (m,lH), 7.2-7.4 (m,5H), 7.5 (m,lH), 7.6 (m,1H).

276 # 3.38 (s,3H), 3.84 (s,3H), 6.71-6.78 (m,3H), 7.0-7.1 (m,2H), 7.2-7.4 (m,SH), 7.54 (m,lH), 7.95 (dd,lH,J=1.7,8.0).

277 # 3.39 (s,3H), 3.85 (s,3H), 6.87 (t,1H), J=2.2), 6.92-6.96 (m,2H), 7.08 (d,1H, J=8.2), 7.17-7.26 (m,2H), 7.3-7.4 (m,3H), 8.3-8.4 (m,2H).

281 # 8.13 (s,2H), 7.86 (s,lH), 7.58 (m,lH), 7.46 (m,2H), 7.24 (m,lH), 5.15 (q,2H), 4.11 (s,3H), 3.9 (s,3H), 3.41 (s,3H).

282 # 7.78 (s,2H), 7.625 (s,1H), 7.42 (m,3H), 7.23 (m,1H), 5.03 (q,2H), 3.92 (d,3H), 3.67 (s,2H), 3.42 (s,3H), 1.905 (s,3H).

283 # 7.45 (m,4H), 7.33 (s,2H), 7.24 (m,1H), 5.12 (q,2H), 4.57 (s,2H), 3.91 (s,3H), 3.43 (s,3H), 1.925 (s,3H).

298 # 8.0 (m,1H), 7.88 (m,1H), 7.625 (m,1H), 7.48 (m,4H), 7.25 (m,1H), 5.09 (m,2H), 4.046 (s,3H), 3.75 (s,3H), 3.49 (s,3H), 2.41 (s,3H), 2.32 (s,3H). Compound is a 1:2 mixture of geometric isomers.

299 # 7.85 (m,1H), 7.75 (m,1H), 7.38 (m,6H), 5.10 (q,2H), 4.10 (s,2H), 3.91 (s,3H), 3.44 (s,3H), 1.95 (s,3H).

300 # 3.41 (s,3H), 3.88 (s,3H), 4.02 (s,3H), 5.17 (AB q,2H), 7.25 (m,1H), 7.46 (m,4H), 7.64 (m,1H), 7.8 (m,4H), 8.12 (s,1H).

301 6 3.37 (s,3H), 3.86 (s,3H), 6.7-6.9 (m,3H), 7.0-7. 1 (m,3H), 7.2-7.5 (m,4H), 7.61(d,2H,J=9.0).

302 3.37 (s,3H), 3.86 (s,3H), 6.8-6.9 (m,3H), 7.03 (dd,2H,J=2.3,7. 1), 7.1 (m,lH), 7.25 (m,lH), 7.3-7.5 (m,3R), 8.21 (dd,lR,J=2.3,7.1).

305 87.37 (m,2H), 7.26 (m,3H), 7.02 (m,3H), 3.86 (s,3R), 3.37 (s,3R).

307 6 8.30 (d,lH), 7.85 (dd,lH), 7.60-7.40 (m,3H), 7.20 (d,lH), 6.70 (d,lH), 5.21 (AB q,2H), 3.94 (s,3H), 3.89 (s,3H), 3.41(s,3H), 2.17 (s,3H).

308 87.41 (m,3H), 7.21 (m,3H), 7.14 (m,lR), 5.06 (q,2R), 3.9 (s,3H), 3.58 (s,2H), 3.43 (s,3H), 1.89 (s,3H).

311 # 8.18 (m,2H), 7.65 (m,1H), 7.55 (t,1H), 7.49 (s,2H), 7.13 (t,2H).

<BR> <BR> <BR> <BR> 3.78 (s,3H), 3.36 (s,3H). <BR> <BR> <BR> <BR> <BR> <BR> <BR> <P>314 # 3.39 (s,3H), 3.85 (s,3H), 6.8-7.0 (m,4H), 7.0-7.1 (m,2H), 7.2 (m,1H).

7.3-7.4 (m,3H), 7.69 (m,1H), 8.19 (dd,1H,J=1.8,5.0).

315 F 3.40 (s,3H), 3.84 (s,3H), 6.9-7.0 (m,3H), 7.0-7.1 (m.2H), 7.2-7.3 (m,lH), 7.35-7.40 (m,3H), 8.55 (d.2H,J=4.7).

316 6 2.38 (s,3H), 3.36 (s,3H), 3.79 (s,3H), 6.35 (d, 1H,J=0.7). 7.0 (m,2H), 7.2-7.25 (m,2H), 7.3-7.6 (m,4H), 8.41 (d,lH,J=0.7).

334 88.08 (d,2H), 7.65 (d,lH), 7.55 (m,lH), 7.49 (m,2H), 7.28 (d,2H), 3.77 (s,3H), 3.37 (s,3H), 2.52 (s,3H).

336 s 7.41 (m,4H), 7.26 (m,2H), 7.21 (m,lH), 7.02 (d,lH), 3.81 (s,3H), 3.357 (s,3H).

337 [in Me2SO-d6]: # 7.92-7.45 (m,8H), 3.79 (s,3H), 3.25 (s,3H).

339 # 2.88 (s,3H), 3.37 (s,3H), 3.79 (s,3H), 6.35 (d,1H,J=0.7), 6.9 (m,2H), 7.10(d,lH,J=7.5), 7.3-7.5 (m,5H), 8.43 (d,lH,J=0.7).

342 6 8.22 (d,2H), 7.61-7.48 (m,4H), 7.28 (m,2H), 3.78 (s,3H), 3.36 (s,3H).

344 88.19 (d,2H), 7.65-7.50 (m,211), 7.49 (s,2H), 7.17 (d,2H). 6.57 (t, I Rj, 3.78 (s,3H), 3.36 (s,3H).

346 # 7.86 (d,1H), 7.77 (m,1H), 7.55 (m,1H), 7.44 (m,2H), 7.23 (d,1H).

6.95 (d,lR), 5.24 (q,2H), 4.44 (q,2H), 3.9 (s,3H). 3.4 (s,3H), 2. 18 (s,3H).

347 # 7.79 (t,1H), 7.57 (d,2H), 7.5 (m,3H), 7.23 (m,2H), 5.12 (AB q,2H), 3.98 (s,3H), 3.88 (s,3H), 3.42 (s,3H).

352 # 2.22 (s,3H), 3.38 (s,3H), 3.82 (s,3H), 6.60-6.66 (m,3H), 6.97 (m,1H), 7.0-7.1 (m,2H), 7.1-7.3 (m,4H), 7.4-7.5 (m,2H).

353 # 7.53 (m,2H), 7.45 (m,2H), 3.81 (s,3H), 3.40 (s,3H), 2.15 (m,1H).

1.0 (m,4H).

354 # 7,56 (m,1H), 7.50 (m,1H), 7.46 (m,2H), 3.79 (s,3H), 3.40 (s,3H).

3.23 (t,lH), 2.05 (br m,2H), 1.90 (br m,2H), 1.80 (br m,2H), 1.7() (br m,2H).

355 [in C6D6]: # 7.7 (d,2H), 7.2 (d,2H), 6.85 (m,4H), 6.6 (d,1H), 6.2 (d,1H), 5.35 (d,1H), 4.75 (d,1H), 3.10 (s,3H).

356 # 8.09 (d,2H), 7.65 (d,1H), 7.55 (m,lH), 7.5-7.35 (m,4H), 3.70 (s,3H), 3.24 (s,3H).

357 # 7.49 (s,lH), 7.4 (m,lH), 7.3 (d,lH), 7.1 (m,2H), 5.19 (dd,2H), 3.90 (s,3H), 3.44 (s,3H).

360 # 8.2 (s,lH), 7.95 (d,1H), 7.8 (d,lH), 7.6 (d,lH), 7.45 (m,3H), 7.25 (1H), 5.25 (m,2H), 3.89 (s,3H), 3.41 (s,3H), 2.22 (s,3H), 1.6 (s,9H).

363 # 8.1 (d,1H), 8.0 (s,lH), 7.75-7.6 (m,2H), 7.55-7.4 (m,3H), 7.3 (m,1H), 3.45 (s,3H).

364 8 8.24 (s,lH), 8.0 (d,1H), 7.65 (m,2H), 7.5 (m,3H). 3.45 (s,3H).

367 # 8.26 (d,2H), 7.75-7.6 (m,4H), 7.55-7.45 (m,2H), 3.45 (s,3H).

368 # 8.06 (d,2H), 7.75 (d,1H), 7.7-7.6 (m,1H), 7.5-7.4 (m, 4H), 3.46 (s,3H).

1.34 (s,9H).

369 # 7.71 (d,1H), 7.65-7.55 (m,1H), 7.5-7.4 (m,2H), 3.49 (s,3H), 1.35 (s,9H).

370 83.34 (s,3H), 3.76 (s,3H). 6.49 (d,1H,J=7.9), 6.53 (d,1H,J=7.9).

7.1-7.2 (m,3H), 7.2-7.4 (m,6H), 7.64 (t,1H,J=8.0).

372 8 3.40 (s,3H), 3.74 (s,3H), 3.84 (s,3H), 6.5-6.6 (m,2H), 6.7 Im, 1H), 6.95 (m,lH), 7.2-7.3 (m,2H), 7.3-7.4 (m,2H), 7.6-7.7 (m,1H), 8.07 dd,1H,J=1.8, 8.1), 8.15 (dd,lH,J=1.7,7.8).

373 # 7.93 (m,3H), 7.56 (m,1H), 7.43 (m,2H), 7.25 (m,1H), 5.3 (q,2H), 3.89 (s,3H), 3.4 (s,3H), 2.15 (s,3H).

374 # 7.5 (d,1H), 7.4 (m,4H), 7.2 (d,1H), 7.1 (d,2H), 5.1 (q,2H), 3.89 (s,3H), 3.4 (m,SH), 1.715 (s,3H), 0.252 (s,lOH).

375 # 7.4-7.6 (m,5H), 7.2 (d,2H), 7.1 (d,2H) 5.0-5.2 (q,2H), 3.5 (s,4H), 3.382 (s,2H), 1.695 (s,3H), 0.250 (s,10H).

381 # 3.4 (s,3H), 3.8 (s,3H), 7.2-7.6 (m,6H), 7.8 (d,1H), 8.0 (s,1H).

384 # 3.34 (s,3H), 3.82 (s,3H), 7.05 (m,1H), 7.21 (m,2H), 7.36-7.50 (m,5H), 7.71 (d,1H), 7.81 (d,2H).

386 # 2.33 (s,3H), 3.38 (s,3H), 3.83 (s,3H), 6.65-6.75 (m,3H), 6.95 (d,2H,J=8.5), 7.01 (dd,1H,J=1.3,8.3), 7.14 (d,2H,J=8.2), 7.2-7.3(m,2H), 7.3-7.4 (m,2H).

387 # 3.39 (s,3H), 3.82 (s,3H), 3.83 (s,3H), 6.65-6.72 (m,3H), 6.99-7.04 (m,2H), 7.2-7.3 (m,3H), 7.3-7.4 (m,2H), 7.5 (m,1H), 7.91 (dd,lH,J=1.8,7.8) 389 8 2.05 (s,3H), 3.39 (s,3H), 3.83 (s,3H), 6.7-6.8 (m,3H), 6.8-6.9 (m,2H), 6.95 (m,lH), 7.0 (m,lH), 7.2-7.3 (m,3H), 7.3-7.4 (m,2H).

390 # 8.15 (s,1H), 8.05 (m,lH), 7.65 (d,lH), 7.55 (t,lH), 7.46 (m,4H), 3.70 (s,3H), 3.24 (s,3H).

391 # 7.80 (s,1H), 7.65 (d,1H), 7.45 (m,2H), 7.35 (m,2H), 7.30-7.20 (m,3H), 6.53 (s,lH), 5.50 (d,1H), 5.35 (d,1H), 3.80 (s,3H), 3.43 (s,3H).

392 # 7.67 (d,2H), 7.62 (d,1H), 7.60-7.35 (m,4H), 3.77 (s,3H), 3.35 (s,3H).

393 # 7.55 (m,2H), 7.45 (m,2H), 3.89 (s,3H), 3.42 (s,3H), 3.40 (s,3H).

394 # 7.63 (d,2H), 7.5 (m,1H), 7.43 (m,1H), 3.5 (s,3H), 3.42 (s,3H).

395 # 8.18 (d,2H), 7.75-7.6 (m,2H), 7.55-7.45 (m,2H), 7.25 (m,2H), 3.45 (s,3H).

396 8 3.4 (s,3H), 3.9 (s,3H), 7.3-7.6 (m,8H), 8.1 (d, I H).

397 # 3.4 (s,3H), 3.9 (s,3H), 7.38-7.5 (m,7H), 8.2 (1H), 7.61 (d,1H).

400 # 7.93 (t,1H), 7.845 (t,1H), 7.77 (t,1H), 7.57 (m,1H), 7.45 (m,2H).

7.25 (m,1H), 5.12 (q,2H), 40 (s,3H), 3.9 (s,3H), 3.43 (s,3H).

401 # 7.74 (s,1H), 7.6 (m,2H), 7.45 (m,2H), 7.31 (d,1H), 7.2 (m,1H), 5.13 (AB q,2H), 4.06 (s,3H), 3.90 (s,3H), 3.42 (s.3H).

402 # 7.85 (1H), 7.65 (m,2H), 7.4 (m,2H), 7.25 (m,2h), 4.6 (m,2H), 3.94 (s,3H), 3.39 (s,3H).

406 # 7.87 (d,2H), 7.45-7.35 (m,3H), 7.3 (m,2H), 7.07 (t,2H), 5.33 (s,2H), 3.92 (s,3H), 3.46 (s,3H).

410 8 3.4 (s,3H), 3.89 (s,3H), 7.4-7.73 (m,8H).

411 8 3.4 (s,3H), 3.87 (s,3H), 7.3-7.6 (m,12H).

412 # 2.3 (s,9H), 3.4 (s,3H), 3.87 (s,3H), 7.5 (m,6H), 7.7 (d,2H).

415 8 3.40 (s,3H), 3.80 (s,3H), 6.6-6.8 (m,3H), 6.9-7.1 (m,4H). 7.2 (m,2H), 7.4 (m,3H).

417 # 2.14 (s,3H), 3.35 (s,3H), 3.75 (s,3H), 6.40 (d,1H,J=8.0), 6.48 (d,1H,J=8.0), 7.03 (m,1H), 7.1-7.3 (m,5H). 7.3-7.4 (m,2H).

7.59 (m,1H).

418 # 3.38 (s,3H), 3.82 (s,3H), 6.65-6.75 (m,3H), 7.0-7.3 (m,7H), 7.3-7.4 (m,2H).

419 # 3.38 (s,3H), 3.86 (s,3H), 6.8-6.9 (m,2H), 7.0-7.1 (m,2H), 7.15 (m,lH), 7.2-7.3 (m,lH), 7.4-7.5 (m,3H), 8.35 (m,lH), 8.6 (m,1H).

420 # 3.39 (s,3H), 3.82 (s,3H), 3.83 (s,3H), 6.6-6.7 (m,3H), 6.9-7.0 (m,1H).

7.0 (m,3H), 7.1-7.2 (m,3H), 7.3-7.4 (m,2H).

421 # 3.39 (s,3H), 3.82 (s,3H), 3.93 (s,3H), 6.46 (d,1H,J=7.8), 6.66 (d,1H,J=7.7), 6.9-7.0 (m.3H), 7.1-7.3 (m.4H). 7.4 (m,2H) 422 # 3.39 (s,3H), 3.85 (s,3H), 6.68 (d,1H,J=6.5), 6.85-6.95 (m,3H), 7.04 (dd,lH,J=1.2,8.3), 7.25 (m,lH), 7.30-7.45 (m,4H).

423 # 3.38 (s,3H), 3.83 (s,3H), 6.7-6.8 (m,3H), 7.0-7.1 (m,2H), 7.2-7.3 (m,3H), 7.4 (m,2H), 7.5 (m,lH), 7.66 (m,lH).

424 # 2.13 (s,6H), 3.38 (s,3H), 3.81 (s,3H), 6.5 (m,2H), 6.6 (m,lH), 7.0-7.2 (m,6H), 7.35 (m,2H).

425 8 3.4 (s,3H), 3.89 (s,3H), 7.4 (m,5H), 7.7 (s,2H).

427 # 8.18 (s,lH), 8.05 (d,lH), 7.75 (m,2H), 7.55 (m,2H), 7.4 (m,2H), 3.45 (s,3H).

428 # 3.4 (s,3H), 3.89 (s,3H), 7.3-7.6 (m,6H), 7.65 (d,1H), 7.8 (3,1H).

430 # 7.65 (d,1H), 7.05-7.6 (m,11H), 6.9 (d,1H), 5.15 (m,2H), 3.89 (s,3H), 3.38 (s,3H).

442 # 7.82 (t,1H), 7.64 (m,3H), 7.44 (m,3H), 7.25 (m,1H), 6.71 (s,1H), 5.13 (q,2H), 4.0 (s.3H), 3.88 (s,3H), 3.41 (s,3H).

447 # 3.39 (s,3H), 3.83 (s,3H), 6.60-6.75 (m,3H), 7.00-7.10 (m,3H), 7.2-7.4 (m,SH), 7.62 dd,1H,J=1.6,7.8).

448 # 1.19 (t,3H), 2.62 (q,2H,J=7.5), 3.39 (s,3H), 3.82 (s,3H), 6.60-6.70 (m,3H), 6.95 (m,lH), 7.05 (m,1H), 7.1-7.3 (m,SH), 7.38 (m,2H).

449 # 7.55 (m,2H), 7.47 (m,2H), 3.86 (s,3H), 3.39 (s,3H).

452 8 8.05 (s,1H), 7.65 (d,1H), 7.60 (m,lH), 7.55 (m,lH), 7.45 (m,2H), 7.35 (m,lH), 3.78 (s,3H), 3.36 (s,3H).

453 # 7.75 (s,1H), 7.60 (d,1H), 7.55 (m,1H), 7.45 (m,2H), 7.40 (d,1H), 7.10 (m,1H), 3.79 (s,3H), 3.38 (s,3H).

454 # 3.4 (s,3H), 3.87 (s,3H), 7.3-7.6 (m,13H).

455 # 3.4 (s,3H), 3.9 (s,3H), 7.4-7.6 (m,4H), 8.0 (s,1H), 8.3 (s,2H).

462 # 7.65-7.55 (m,2H), 7.5-7.45 (m,3H), 7.04 (d,1H). 3.80 (s,3H).

3.38 (s,3H).

466 # 3.408 (s,3H), 3.89 (s,3H), 7.4-7.6 (m,3H), 7.7 (d,1H), 7.9 (d,1H).

467 8 8.2 (s,lH), 8.1 (d,lH), 7.6 (d,1H), 7.35-7.55 (m,5H), 3.84 (s,3H), 3.40 (s,3H).

468 # 3.35 (s,3H), 3.84 (s,3H), 3.88 (s,3H), 7.0 (m,4H), 7.2 (m,2H), 7.4 (m,2H), 7.71 (dd,2H), 8.03 (s,lH).

469 # 3.38 (s,3H), 3.86 (s,3H), 6.68 (d,1H,J=8.5), 6.80 (m,1H), 6.82-6.91 (m,3H), 7.07 (dd,1H,J=1.0,8.2), 7.2(m,1H), 7.3-7.5 (m,4H) 470 # 3.40 (s,3H), 3.83 (s,3H), 6.66 (m,2H), 6.76 (m,1H), 7.04 (d,1H,J=8.2), 7.2-7.5 (m,7H).

471 # 3.40 (s,3H), 3.83 (s,3H), 6.6 (m,1H), 6.65 (m,1H), 6.80 (m,1H), 7.00 (m,lH), 7.2-7.3 (m,2H),7.35-7.40 (m,2H), 7.55-7.60 (m,1H), 8.19 (d,2H,J=8.2).

472 8 3.38 (s,3H), 3.84 (s,3H), 6.7-6.9 (m,SH), 7.0-7.5 (m,6H).

473 # 2.16 (s,3H), 2.29 (s,3H), 3.38 (s,3H), 3.83 (s,3H), 6.6-6.7 (m,3H), 6.76 (m,lH), 6.89 (dslH,J=7.8), 7.02 (m,lH, 7.1 (m,1H), 7.2-7.3 (m,2H), 7.3-7.4 (m,2H).

479 # 7.57 (m,2H) 7.44 (m,2H), 7.24 (m,2H), 7.05 (d,1H), 5.21 (q,2H), 3.89 (s,3H), 3.4 (s,3H), 3.02 (m,2H), 2.15 (s,3H), 1.95 (m,2H), 1.33 (s,6H).

480 # 7.48 (m,4H), 7.27 (m,3H), 5.23 (q,2H), 3.89 (s,3H), 3.66 (t,2H), 3.4 (s,3H), 3.09 (t,2H), 2.17 (s,3H), 2.06 (m,2H).

481 # 7.5 (m,4H), 7.2(m,2H), 7.03 (d,1H), 5.26 (AB q,2H), 3.46 (s,3H), 3.01 (m,2H), 2.14 (s,3H), 1.9 (m,2H), 1.32 (s,6H).

482 # 7.51 (m,4H), 7.26 (m,3H), 5.22 (dd,2H), 3.65 (t,2H), 3.46 (s,3H), 3.08 (t,2H), 2.15 (s,3H), 2.08 (m,2H).

483 87.55 (d,lH), 7.45 (m,2H). 7.2-7.35 (m,4H), 6.95 (d,1H), 5.25 (m,2H), 4.4 (m,2H), 3.88 (s,3H), 3.40 (s,3H), 2.18 (s,3H).

485 # 7.6-7.45 (m,5H), 3.82 (s,3H), 3.38 (s,3H).

490 8 8.35 (s,lH), 8.15 (d,1H), 7.7-7.4 (m,8H), 7.36 (m,3H), 3.78 (s,3H), 3.37 (s,3H).

492 88.15 (s,lH), 8.00 (d,1H), 7.65-7.30 (m,6H), 4.24 (q,2H), 3.76 (s,3H), 3.37 (s,3H), 1.48 (t,3H).

493 # 8.35 (s,1H), 8.15 (d,1H), 7.7-7.4 (m,7H), 7.09 (m,3H), 3.79 (s,3H), 3.38 (s,3H).

494 # 8.65 (d,1H), 8.40 (s,1H), 8.20 (d,1H), 7.75-7.4 (m,9H), 3.78 (s,3H), 3.38 (s,3H).

495 # 8.25 (s,lH), 8.10 (d,1H), 7.65-7.45 (m,SH), 7.40 (t,lH), 4.9 (m,lH), 4,51 (m,2H), 3.90 (m,1H), 3.77 (s,3H), 3.60 (m,1H), 3.37 (s,3H), 1.90-1.55 (m,6H).

497 8 10.09 (s,lH), 8.66 (s,lH), 8.45 (d,lH), 8.0 (d,lH), 7.7-7.55 (m,3H), 7.5 (m,2H), 3.80 (s,3H), 3.36 (s,3H).

499 # 3.38 (s,3H), 3.86 (s,3H), 6.75 (s,lH), 6.75-6.83 (m,2H), 6.88 (d,2H,J=1.7), 7.05 (m,2H), 7.09 (t,1H,J=1.7), 7.2-7.4 (m,3H).

503 # 3.38 (s,3H), 3.84 (s,3H), 6.7-6.8 (m,3H), 7.04 (dd,1H,J=1.1,8.2), 7.19-7.45 (m,9H).

504 # 3.38 (s,3H), 3.84 (s,3H), 6.70 (m,2H), 6.75-6.83 (m,4H), 7.04 (dd,lH,J=1.0,8.2), 7.2-7.3 (m,3H). 7.35-7.40 (m,2H).

505 # 3.38 (s,3H), 3.84 (s,3H), 6.7-6.8 (m,3H), 6.8-6.9 (m,1H), 6.9-7.1 (m,3H), 7.2-7.3 (m,2H), 7.35-7.40 (m,2H).

506 # 3.38 (s,3H), 3.83 (s,3H), 6.6-6.7 (m,3H), 6.80-7.00 (m,4H), 7.20-7.25 (m,2H), 7.30-7.40 (m,2H).

508 5 8.9 (s,lH), 8.4 (d,1H), 7.65 (d,lH), 7.55 (m,lH), 7.49 (m,2H), 6.9 (d,1H), 4.82 (q,2H), 3.80 (s,3H), 3.37 (s,3H).

515 # 7.85 (s,1H), 7.8 (d,1H), 7.3-7.6 (m,6H), 3.85 (s,3H), 2.40 (s,3H), 2.49 (s,3H).

526 # 7.57 (m,2H), 7.49 (m,2H), 7.02 (d,1H), 6.45 (d,1H), 3.80 (s,3H), 3.37 (s,3H) 527 # 8.21 (d,2H), 8.1 (d,2H), 7.7-7.4 (m,9H), 3.77 (s,3H), 3.37 (s,3H) 528 # 7.7 (d,1H), 7.6-7.4 (m,5H), 7.25 (m,1H), 6.9 (dd,1H), 6.75 (s,1H), 3.80 (s,3H), 3,34 (s,3H).

530 # 7.55 (m,2H), 7.45 (m,2H), 3.83 (s,3H), 3.39 (s,3H), 1.32 (s,9H).

531 # 7.75 (d,1H), 7.7-7.4 (m,5H), 7.3 (m,1H), 6.95 (dd,1H), 3.77 (s,3H), 3.38 (s,3H), 1.00 (t,9H), 0.76 (q,6H).

532 # 7.75 (d,1H), 7.65 (m,2H), 7.6-7.45 (m,3H), 7.3 (m,1H), 6.9 (m,1H), 3.77 (s,3H), 3.38 (s,3H), 1.00 (s,9H), 0.22 (s,6H).

533 # 8.1 (d,1H), 8.05 (s,1H), 7.65-7.55 (m,2H), 7.5-7.45 (m,3H), 7.3 (dd,1H), 4.88 (s,2H), 3.78 (s,3H), 3.37 (s,3H).

534 # 8.1 (d,1H), 8.0 (s,1H), 7.65-7.45 (m,5H), 7.3 (m,1H), 6.5 (q,1H), 3.78 (s,3H), 3.37 (s,3H), 1.92 (d,3H).

535 # 8.1 (d,1H), 8.0 (s,1H), 7.65-7.55 (m,2H), 7.5-7.45 (m,3H), 7.3 (m,1H).

7.15 (dd,1H), 5.05 (dd,1H), 4.7 (dd,1H), 3.78 (s,3H), 3.37 (s,3H).

536 # 8.05 (d,1H), 7.95 (s,1H), 7.65-7.4 (m,5H), 7.15 (dd,1H), 3.7 (s,3H), 3.37 (s,3H), 1.37 (s,9H).

537 # 7.95 (d,1H), 7.7-7.3 (m,6H), 7.15 (dd,lH), 5.28 (s,2H), 3.8 (s,2H), 3.77 (s,3H), 3.38 (s,3H), 0.95 (m,2H), 0.0 (s,9H).

538 # 8.2 (d,1H), 8.1 (s,1H), 7.65-7.45 (m,5H), 7.35 (dd,1H), 3.80 (s,3H), 3.37 (s,3H).

539 # 7.64 (d,lH), 7.55 (m,lH), 7.47 (m,3H), 3.80 (s,3H), 3.39 (s,3H).

540 # 7.54 (m,2H), 7.46 (m,2H), 7.33 (s,1H), 7.24 (m,3H), 4.09 (s,2H).

3.73 (s,3H), 3.39 (s,3H).

541 #7.53 (m,2H), 7.46 (m,2H), 7.27 (s,4H), 4.08 (s,2H). 3.73 (s,3H).

3.38 (s,3H).

547 [in C6D6]: # 8.15 (s,1H), 8.1 (d,1H), 7.15 (m,1H), 7.1 (t,1H), 7.05 (m,lH), 6.9 (dd,1H), 6.8 (m,2H), 3.25 (s,3H), 3.0 (s,3H), 0.15 (s,9H).

548 # 7.75 (d,lH), 7.7 (s,lH), 7.65 (s,lH), 7.55 (m,lH), 7.5 (m,2H), 7.35 (t,lH), 7.0 (d,lH), 6.15-6.0 (m,lH), 5. 45 (d,lH), 5.3 (d,1H), 4.6 (d,2H), 3.77 (s,3H), 3.37 (s,3H).

549 # 7.8 (d,lH), 7.75 (s,lH), 7.65 (s,lH), 7.55 (m,lH), 7.5 (m,2H), 7.35 (t,lH), 7.05 (dd,1H), 6.05 (s,1H), 5. 7 (s,1H), 4.7 (s,2H), 3.78 (s,3H), 3.37 (s,3H).

553 # 7.3-7.5 (m,3H), 7.2 (s,1H), 4.4-4.7 (q,2H), 3.861 (s,3H), 3.6 (q,2H), 3.384 (s,3H).

554 # 7.65 (s,2H), 7.35-7.6 (m,4H), 7.3 (1H), 7.1 (1H), 3.8 (s,3H), 3.4 (s,3H).

556 # 8.21 (s,1H), 8.05 (d,1H), 7.65 (d,1H), 7.55 (m,1H), 7.5 (m,3H), 7.4 (m,1H), 6.8 (dd,1H), 5.85 (d,1H), 5.3 (d,1H), 3.77 (s,3H), 3.37 (s,3H).

562 # 8.2 (s,1H), 8.1 (d,1H), 7.35-7.65 (m,6H), 3.84 (s,3H), 3.40 (s,3H).

563 [in Me2SO-d6]: # 7.75 (d,1H), 7.65 (m,2H), 7.55 (t,1H), 3.80 (s,3H), 3.5 (m,4H), 3.27 (s,3H), 1.15 (m,6H).

564 # 7.85 (s,lH), 7.75 (d,lH), 7.3-7.6 (m,6H), 3.84 (s,3H), 3.40 (s,3H), 2.9 (m,2H), 1.3 (t,3H).

566 # 8.82 (d,J=5Hz,1H), 7.95 (s,1H), 7.61 (m,1H), 7.47 (m,3H), 7.25 (m,lH), 5.19 (m,2H), 4.11 (s,3H), 3.90 (s,3H), 3.42 (s,3H).

567 8 8.14 (d,2H), 7.6 (d,2H), 7.56 (m,2H), 7.49 (m,2H), 3.78 (s,3H), 3.36 (s,3H), 3.19 (s,lH).

568 # 8.11 (d,2H), 7.6 (m,2H), 7.53 (d,2H), 7.48 (m,2H), 3.77 (s,3H), 3.36 (s,3H), 0.26 (s,9H).

569 # 7.55 (m,2H), 7.46 (m,2H), 3.86 (s,3H), 3.40 (s,3H).

570 # 7.51 (m,5H), 7.26 (m,3H), 5.23 (q,2H), 3.89 (s,3H), 3.41 (s,3H), 2.48 (s,3H), 2.17 (s,3H).

571 # 7.55 (d,lH), 7.39 (m,4H), 7.2 (m,lH), 7.08 (1H), 6.99 (d,1H), 4.34 (m,2H), 3.84 (s,3H), 3.42 (s,3H), 2.46 (s,3H).

572 8 8.25 (m,lH), 8.15 (d,lH), 7.65-7.45 (m,6H), 7.39 (t,lH), 3.78 (s,3H), 3.37 (s,3H).

573 # 7.65 (d,lH), 7.55 (m,lH), 7.49 (m,4H), 6.85 (m,lH), 5.26 (s,4H), 3.77 (m,7H), 3.39 (s,3H), 1.0 (m,4H), 0.00 (s,18H).

575 # 7.78 (distorted d,lH), 7.57-7.50 (m,2H), 7.45-7.40 (m,2H), 7.30-7.28 (m,lH), 7.04 (s,lH), 6.83-6.80 (m,1H), 3.95 (apparent d, 3H), 1.28 (s,9H).

576 # 7.6 (d,1H), 7.45 (m,4H), 7.4 (s,1H), 7.25 (m,2H). 5.0 (m,2H), 3.91 (s,3H), 3.41 (s,3H), 2.24 (s,3H).

577 # 7.55 (m,2H), 7.5 (m,2H), 7.45 (d,2H), 6.67 (t,1H), 4.43 (q,4H), 3.81 (s,3H), 3.33 (s,3H).

580 # 7.55 (s,lH), 7.4 (m,4H), 7.2 (m,lH), 6.7 (m,2H), 4.33 (m,2H), 3.86t(s,3H), 3.43 (s,3H), 2.44 (s,3H).

581 # 7.53 (d,1H), 7.4 (m,2H), 7.2 (m,1H), 7.06 (m,1H), 6.71 (d,2H), 4.32 (q,2H), 3.875 (s,3H), 3.44 (s,3H), 2.46 (s,3H).

598 major component: # 7.33 (d,1H), 6.95 (d,1H), 5.31 (d,2H), 3.904 (s,3H).

3.42 (s,3H). 2.74 (q,2H), 1.11 (t,3H) plus peaks overlapping with minor component at 7.88 (d), 7.79 (m), 7.61 (d), 7.49 (t); minor component: # 6.62 (s,lH), 5.22 (d,2H), 3.899 (s,3H), 3.41 (s,3H).

2.45 (s,3H), 2.22 (d,3H) plus peaks overlapping with major component at 7.88 (d), 7.79 (m), 7.61 (d), 7.49 (t).

604 # 8.69 (m,1H), 7.94 (s,1H), 7.85-7.73 (m,4H), 7.61 (d,1H), 7.59-7.45 (m,2H), 7.38 (dd,1H), 5.50 (AB pattern, 2H), 3.78 (s,3H).

3.35 (s,3H), 2.25 (s,3H).

613 â7.70 (s,lH), 7.54 (m,4H), 7.34 (t,lH), 5.11 (s,2H), 3.86 (s,3H), 3.32 (s,3H), 2.14 (s,3H), 0.28 (s,9H).

614 # 7.86 (s,1H), 7.76 (d,1H), 7.64 (d,1H), 7.59 (d,1H), 7.54 (d,1H), 7.53-7.47 (m,1H), 5.01 (br s,2H), 4.96 (s,2H), 3.89 (s,3H), 3.33 (s,3H).

645 # 7.65 (d,1H), 7.6 (s,1H), 7.4-7.55 (m,4H), 7.35 (t,1H), 7.25 (d,1H), 5.2 (m,2H), 4.0 (m,lH), 3.43 (s,3H), 2.6 (d,3H). 2.23 (s,3H), 0.24 (s,9H).

649 # 7.6 (d,1H), 7.4-7.55 (m,5H), 7.35 (m,2H), 5.24 (s,2H), 3.54 (s,3H), 2.15 (s,3H).

650 # 7.65 (m,2H), 7.55 (s,2H), 7.5 (m,2H), 7.25 (1H), 5.2 (m,2H), 4.1 (m,lH), 3.43 (s,3H), 2.55 (d,3H), 2.24. (s,3H), 0.25 (s,18H).

652 â 7.2-7.7 (m,8H), 5.3 (d,2H), 3.4 (s,3H), 2.6 (s,6H), 2.2 (s,3H), 0.3 (s,9H).

653 # 7.85 (s,lH), 7.75 (d,lH), 7.6 (m,2H), 7.45 (m,3H), 7.2 (d,1H), 5.2 (m,2H), 3.5 (s,3H), 2.2 (s.3H), 2.0 (s,3H).

654 # 7.45 (s,1H), 7.25-7.4 (m,3H), 7.2 (d,1H) 3.55 (s,3H), 2.28 (s,3H).

655 # 7.25-7.4 (m,3H), 7.15 (d,1H), 3.5 (s,3H), 2.3 (m,2H), 2.2 (s,3H).

1.1 (t,3H).

656 # 8.1 (d,1H), 8.0 (s,1H), 7.65-7.4 (m,4H), 7.3 (m,lH). 3.79 (s,3H), 3.36 (s,3H).

658 # 8.03 (s,2H), 7.55 (s,2H), 7.5 (s,1H), 7.45 (s,1H), 3.81 (s,3H), 3.35 (s,3H).

659 # 8.61 (s,2H), 7.95 (s,1H), 7.56 (m,2H), 7.5 (m,lH), 3.82 (s,3H), 3.35 (s,3H).

661 # 8.25 (d,2H). 7.69 (d,2H), 7.59 (d,1H), 7.55-7.5 (m,2H), 3.79 (s,3H), 3.35 (s,3H).

663 # 7.55 (d,1H), 7.5 (m,2H), 3.79 (s,3H), 3.40 (s,3H), 1.35 (s,9H).

664 5 7.98 (d,2H), 7.65 (d,1H), 7.53 (d,2H), 7.5-7.35 (m,2H). 3.77 (s,3H), 3.30 (s,3H).

665 # 8.2 (s,1H), 7.95 (d,lH), 7.65 (d,1H), 7.5-7.35 (m,3H), 3.79 (s,3H), 3.31 (s,3H), 667 # 8.05 (d,1H), 7.95 (s,1H), 7.65 (d,1H), 7.5-7.35 (m,3H), 7.3 (d,1H), 3.77 (s,3H), 3.45 (s,3H).

668 # 7.6 (dd,1H), 7.5 (m,2H), 3.81 (s,3H), 3.36 (s,3H), 1.3(1 (s,9H).

670 # 8.58 (s,2H), 7.95 (s,lH), 7.65 (d,1H), 7.5-7.35 (m,2H), 3.80 (s,3H), 3.31 (s,3H).

671 # 8.04 (d,2H), 7.6 (dd,1H), 7.43 (d,4H), 3.75 (s,3H), 3.31 (s,3H), 1.32 (s,9H).

# 2.22 (s,3H), 2.25 (s,3H), 3.39 (s,3H), 3.82 (s,3H), 6.80-6.90 (m,3H), 6.82 (d,1H,J=8.2), 6.93 (d,1H,J=7.7, 7.05-7.10 (m,2H), 7.15-7.30 (m,4H).

682 # 2.26 (s,3H), 3.39 (s,3H), 3.82 (s,3H), 6.65 (m,1H), 6.70 (m,2H), 6.84 (d,lH,J=7.5), 7.0-7.1 (m,4H), 7.2-7.4 (m,4H).

683 # 2.26 (s,3H), 3.39 (s,3H), 3.83 (s,3H), 6.6-6.7 (m,3H), 6.84 (d,1H,J=7.4), 7.0-7.15 (m,3H), 7.2-7.3 (m,3H), 7.49 (dd,lH,J=1.7,7.9).

684 # 2.26 (s,3H), 3.39 (s,3H), 3.82 (s,3H), 6.6-6.7 (m,3H), 6.84 (d,1H,J=7.7), 7.0-7.2 (m,SH), 7.25 (m,lH), 7.28 (m,lH).

688 # 2.26 (s,3H), 3.38 (s,3H), 3.84 (s,3H), 6.63 (t,1H,J=2.2), 6.68 (m,2H).

6.83 (d,1H,J=8.0), 6.95-7.10 (m,SH), 7.2 (m,1H), 7.26 (m,lH).

689 # 2.26 (s,3H), 3.39 (s,3H), 3.81 (s,3H), 6.6-6.7 (m,3H), 6.82 (m,1H).

6.95-7.05 (m,3H), 7.1-7.2 (m,2H), 7.28 (m,lH).

692 # 7.99 (s,2H), 7.50 (m,lH), 7.38 (m,2H), 3.82 (s.3H). 3.38 (s,3H).

2.32 (s,3H).

700 # 7.35 (d,J=9.0Hz,1H), 7.15 (d,J=2.7Hz,lH), 6.93 (dd,J=9.0, 2.7 Hz,IH).

3.85 (s,3H), 3.78 (s,3H), 3.39 (s,3H), 1.37 s,9H).

707 # 2.28 (s,3H), 3.36 (s,3H), 3.91 (s,3H), 6.85 (m,lH), 6.9-7.0 (m,2H), 7.25 (m,lH), 7.3-7.4 (m,2H).

726 # 2.26 (s,3H), 3.39 (s,3H), 3.83 (s,3H), 6.6-6.7 (m,3H), 6.80-6.85 (m,1H), 7.0-7.1 (m,3H), 7.2-7.4 (m,3H), 7.61 (dd,lH,J=1.4,7.8).

739 # 8.0 (s,2H), 7.85 (s,1H), 7.55 (d,1H), 7.45 (m,2H), 7.3 (1H), 7.2 (t,1H), 5.45 (m,2H), 5.3 (m,2H), 3.42 (s,3H), 2.22 (s,3H).

743 # 7.5 (m,3H), 7.2 (d,lH), 5.8 (ABq,2H), 3.93 (s,3H), 3.52 (s,3H), 1.97 (s,3H), 1.92 (s,3H).

744 â 7.4-7.6 (m,2H), 7.2 (m,2H), 5.18 (ABq, 2H), 3.93 (s,3H), 3.91 (s,3H), 3.43 (s,3H), 1.98 (s,3H), 1.94 (s,3H).

747 # 7.57 (m,1H), 7.38 (m,2H), 7.2 (m,1H), 4.22 (m,2H), 4.12 (q,2H).

3.92 (s,3H), 3.43 (s,3H), 3.2 (m,2H), 2.05 (s,3H), 0.9 (m,9H).

758 # 7.00-7.53 (m,9H), 4.87 (ABq,2H), 3.87 (s,3H, OC3), 3.41 (s,3H, NCH3), 2.2 (s,3H, N=CCH3).

759 [in Me2SO-d6]: â 8.02 (bs,1H), 7.94 (d,2H), 7.73 (d,2H), 7.50 (m,4H), 7.39 (bs,1H), 7.30 (m,2H), 7.15 (d,1H), 6.98 (d,1H), 3.79 (s,3H), 3.21 (s,3H).

760 # 9.38 (s,1H), 8.12 (d,2H), 7.73 (m,1H), 7.35-7.65 (m,5H), 7.21 (m,1H), 4.61 (ABq,2H), 3.48 (s,3H).

761 # 7.58 (s,1H), 7.37 (m,2H), 7.14 (m,3H), 6.98 (t,1H), 6.67 (d,1H), 4.32 (q,2H), 3.76 (s,3H), 3.43 (s,3H), 2.43 (s,3H). 1.97 (s,3H).

762 # 7.56 (s,1H), 7.38 (m,2H), 7.2 (m,2H), 6.89 (d,1H), 6.63 (m,2H), 4.2 (m,2H), 3.86 (s,3H), 3.4 (s,3H), 2.43 (s,3H), 2.32 (s,3H).

763 # 7.55 (d,lH), 7.4 (m,2H), 7.17 (m,3H), 6.98 (m,1H), 6.75 (m,lH), 4.35 (m,2H), 3.86 (s,3H), 3.43 (s,3H), 2.45 (s,3H).

767 # 8.30 (d,lH), 7.3-7.5 (m,4H), 6.59 (d,lH), 4.68 (q,2H), 3.8 (s,3H), 3.3 (s,3H).

768 # 7.61 (d,1H), 7.38 (m,3H), 7.18 (m,2H), 7.01 (m,1H), 6.81 (m,1H), 4.38 (m,2H), 3.83 (s,3H), 3.44 (s,3H).

769 # 7.57 (m,lH), 7.38 (m,2H), 7.19 (d,1H), 6.81 (m,4H), 4.3 (m,2H), 3.86 (s,3H), 3.78 (s,3H), 3.42 (s,3H), 2.42 (s,3H).

771 # 7.8 (m,1H), 7.55-7.47 (m,4H), 7.4 (m,2H), 7.3 (m,2H), 7.14 (s,1H), 7.1-7.0 (m, 2H), 3.96 (s,3H), 3.39 (d, 3H).

772 # 7.4-7.35 (m,3H), 7.3-7.2 (m,3H), 7. 1-7.0 (m,2H), 5.08 (s,2H), 3.88 (s,3H), 3.44 (s,3H), 773 # 8.02 (dd,1H), 7.68 (m,2H), 7.52 (t,1H), 7.44 (s,1H), 7.26 (s,1H), 3.49 (s,3H).

774 # 7.5 (m,lH), 7.41 (m,2H), 7.24 (m,lH), 5.08 (d,2H), 3.94 (s,3H), 3.45 (s,3H), 2.33 (s,3H), 1.23 (s,9H).

775 # 7.45 (m,5H), 7.24 (m,3H), 5.24 (q,2H), 3.9 (s,3H), 3.41 (s,3H), 2.49 (s,3H), 2.17 (s,3H).

776 # 7.92 (s,1H), 7.83 (d,1H), 7.52 (m,5H), 7.25 (m,1H), 5.33 (q,2H), 4.54 (q,2H), 3.91 (s,3H), 3.41 (s,3H).

778 # 8.43 (d,1H), 7.5 (m,1H), 7.38 (m,3H), 6.36 (d,1H), 4.81 (q,2H), 3.79 (s,3H), 3.34 (s,3H).

779 # 7.88 (m,1H), 7.74 (d,1H), 7.50 (m,5H), 7.24 (m,1H), 5.25 (q,2H), 3.9 (s,3H), 3.41 (s,3H), 2.75 (s,3H), 2.23 (s,3H).

780 # 8.17 (s,1H), 7.9 (m,2H), 7.53 (m,2H), 7.43 (m,2H), 7.22 (m,1H), 5.26 (q,2H), 3.9 (s,3H), 3.4 (s,3H), 3.08 (s,3H), 2.22 (s,3H).

791 # 8.74 (m,1H), 8.3 (d,1H), 8.1 (d,1H), 7.7-7.4 (m,3H), 7.4-7.2 (m,1H), 7.2-7.1 (m,1H), 3.77 (s,3H), 3.38 (s,3H), 1.61 (s,9H).

792 # 7.9 (s,1H), 7.75 (d,1H), 7.65 (d,1H), 7.35-7.55 (m,5H), 7.25 (1H), 4.9-5.1 (m,2H) 3.94 (s,3H), 3.43 (s,3H), 2.27 (S,3H).

794 # 7.6-7.4 (m,4H), 3.83 (s,3H), 3.40 (s,3H), 1.58 (s,9H).

797 5 8.3 (d,1H), 7.3-7.5 (m,4H), 6.55 (d,lH), 4.68 (q,2H), 3.81 (s,3H), 3.31 (s,3H).

799 # 8.39 (s,1H), 7.21-7.51 (m,7H), 6.46 (d,1H, J=0.4), 3.77 (s,3H), 3.37 (s,3H).

800 # 8.41 (d,1H, J=0.8), 7.24-7.51 (m,6H), 7.03-7.06 (m,1H), 6.33 (d,1H, J=0.8), 3.78 (s,3H), 3.36 (s,3H), 2.55 (q,2H. J=7.5), 1.19 (t,3H, J=7.6).

801 # 7.42 (m,4H), 6.42 (s,lH), 4.61 (q,2H), 3.83 (s,3H), 3.3 (s,3H), 2.4 (s,3H).

805 # 7.54 (m,2H), 7.46 (m,2H), 7.41 (m,lH), 7.24 (m,2H), 4.22 (s,2H), 3.78 (s,3H), 3.39 (s,3H).

806 # 7.53 (m,2H), 7.46 (m,3H), 7.37 (d,lH), 7.20 (d,2H). 4.06 (s,2H), 3.76 (s,3H), 3.38 (s,3H).

807 # 7.54 (m,2H), 7.49 (s,1H), 7.46 (m,2H), 7.40 (m,1H), 7.18 (m,2H), 4.08 (s,2H), 3.73 (s,3H), 3.39 (s,3H).

812 # 7.56-7.51 (m,4H), 7.46 (m,4H), 4.17 (s,2H), 3.74 (s,3H), 3.37 (s,3H) 816 # 7.60 (s,lH), 7.54-7.51 (m,4H), 7.46 (m,3H), 4.17 (s,2H), 3.72 (s,3H).

3.38 (s,3H).

819 # 7.82 (s,2H), 7.78 (s,1H), 7.53 (m,2H), 7.46 (m,2H), 4.23 (s,2H), 3.77 (s,3H), 3.38 (s,3H), 821 # 8.25 (s,1H), 8.15 (s,1H), 8.00 (d,1H), 7.90 (d,1H), 7.80 (m,2H), 7.49 (m,3H). 3.81 (s,3H), 3.34 (s,3H).

822 # 8.40 (s,1H), 8.10 (s,1H), 7.95 (m,2H), 7.60-7.40 (m,5H), 4.20 (s,2H), 3.79 (s,3H), 3.36 (s,3H).

823 # 8.40 (d,1H), 8.20 (s,1H), 7.59 (m,3H), 7.50 (m,4H), 3.82 (s,3H), 3.37 (s,3H).

824 # 8.50 (s,1H), 8.15 (s,1H), 8.05 (d,1H), 7.95 (d,1H), 7.59-7.40 (m,5H), 3.80 (s,3H), 3.35 (s,3H), 825 8 7.65-7.40 (m,7H), 6.80 (d,lH), 3.76 (s,3H), 3.37 (s,3H), 3.01 (s,6H).

826 # 7.6 (m,1H), 7.46 (m,3H), 7.25 (m,4H), 6.96 (m,1H), 3.92 (s,3H), 3.39 (s,3H), 2.3 (s,3H).

829 # 8.2 (d,1H), 8.1 (s,1H), 7.7-7.4 (m,5H), 7.3 (d,1H), 3.81 (s,3H), 3.40 (s,3H), 3.36 (s,3H).

830 # 8.2 (m,2H), 7.7-7.4 (m,6H), 3.81 (s,3H), 3.55 (s,3H), 3.37 (s.3H).

838 # 8.31 (s,lH), 8.0 (m,lH), 7.7 (d,1H), 7.5 (t,lH), 7.4 (t,lH), 7.2- 7.3 (m,9H, including CHC13), 7.0 (d,2H), 5.37 (s,2H), 5.1-5.3 (ABq,2H), 3.47 (s,3H).

844 # 7.55-7.42 (m,3H), 7.4-7.3 (m,4H), 7.25-7.20 (m,2H), 3.54 (s,3H), 3.36 (s,3H).

845 # 7.55-7.40 (m,4H), 7.40-7.30 (m,3H), 7.22 (d,2H), 7.13 (t, I H).

7.04-6.95 (m,3H), 3.63 (s,3H), 3.36 (s,3H).

846 # 8.00 (d,lH), 7.90 (s,lH), 7.61 (d,1H), 7.55 (t,lH), 7.49 (m,2H), 7.45 (t,1H), 7.20 (d,1H), 6.80-6.40 (t,1H), 3.79 (s,3H), 3.36 (s,3H).

847 # 9.46 (s,1H), 8.15 (m,2H), 7.46 (m,4H), 7.21 (m,2H), 3.78 (s,3H), 3.29 (s,3H).

849 # 8.12 (m,2H); 7.61 (m,2H); 7.50 (m,2H); 7.38 (m,2H); 7.13 (d,1H); 6.93 (d,1H); 3.78 (s,3H); 3.37 (s, 3H).

854 5 8.93 (s,lH), 7.75-7.42 (m,SH), 3.79 (s,3H), 3.37 (s,3H).

855b # 3.69 (s,3H), 3.25 (s,3H), 2.72 (s,3H).

856 8 7.3 (m,7H), 3.94 (s,3H), 3.86 (s,3H), 3.36 (s,3H).

858 5 9.26 (s,lH), 7.40 (m,8H), 3.73 (s,3H), 3.31 (s,3H), 2.40 (s,3H).

877 # 7.55 (d,1H), 7.32-7.51 (m, 6H), 7.18 (d,1H), 3.84 (s,3H), 3.40 (s,3H), 2.90 (q,2H), 1.31 (t,3H).

878 # 7.59 (d,1H), 7.45-7.56 (m,2H), 7.31-7.43 (m,4H), 7.21 (d,1H).

3.81 (s,3H), 3.39 (s.3H), 0.21 (s,9H).

884 # 7.72-7.65 (m,4H), 7.48-7.30 (m,10H), 7.2 (m,1H), 6.40 (m,1H).

6.28 (m,1H), 4.85 (ABq,2H), 3.80 (s,3H), 3.37 (s,3H), 1.08 (s,9H).

885 # 8.05 (s,2H), 7.8 (s,1H), 7.3-7.6 (m,4H), 3.87 (s,3H), 3.40 (s,3H), 2.51 (s,3H).

886 # 8.07 (dd,1H), 7.58 (dd,1H), 7.50 (dd,1H), 7.20 (dd,1H), 6.84 (s,1H), 3.95 (s,3H), 3.48 (s,3H), 896 # 7.62 (dd,2H,J=2.2, 6.8), 7.22-7.30 (m, 2H), 7.07 (d,lH,J=7.5), 6.84 (d,1H,J=8.0), 6.78 (dd,2H,J=2.1, 6.9), 6.70-6.74 (m,2H), 6.67 (m,1H), 3.38 (s,3H), 3.38 (s,3H), 2.26 (s,3H).

901 # 7.68 (s,1H), 7.55 (d,1H), 7.47 (s,2H), 7.35 (s,1H), 7.15 (d,1H), 5.13 (ABq, 2H ArCH2O) 3.89 (s,3H, OCH3), 3.42 (s,3H, NCH3), 2.17 (s,3H, N=CCH3).

902 # 8.31 (d,1H,J=5.5), 7.35 (t,1H,J=8.0), 7.1-7.3 (m,6H), 6.58 (d,1H,J=5.5).

3.79 (s,3H), 3.33 (s, 3H), 2.26 (s,3H).

903 # 8.35 (d,1H, J=5.7), 7.26 (m,1H), 7.26 (m,1H), 7.1-7.3 (m,6H), 6.66 (d,1H, J=5.5), 3.73 (s,3H), 3.33 (s,3H), 2.26 (s,3H).

905 5 6.95-7.38 (m,6H), 5.09 (s,2H, PhOCH2), 3.81 (s,3H, OCH3), 3.55 (s,3H, NCH3), 2.14 (s,3H, PhCH3).

914 # 7.85 (s,lH), 7.8 (d,1H), 7.5-7.6 (m,2H), 7.3-7.45 (m,2H), 7.2 (d, I H).

3.85 (s,3H), 3.41 (s,3H), 2.48 (s,3H), 2.29 (s,3H).

919 # 8.40 (dt, 1H), 8.145 (d,1H), 7.82 (d,2H), 7.75 (d,1H), 7.62 (d,1H), 7.48 (t,lH), 5.32 (ABq, 2H) 3.51 (s,3H), 2.24 (s,3H).

924 # 7.83 (s,lH), 7.78 (d,lH), 7.58 (d,lH), 7.50 (m,2H), 7.04 (dt, 1H), 6.76 (d,1H), 5.15 (ABq,2H), 3.84 (s,3H), 3.46 (s,3H), 2.18 (s,3H).

925 # 7.46 (m,3H), 7.33 (s,1H), 7.03 (dt, 1H), 6.77 (d,1H), 5.14 (ABq,2H), 3.84 (s,3H), 3.49 (s,3H), 2.11 (s,3H).

931 # 7.48 (d,2H), 7.32 (d,1H), 7.21 (d,2H), 5.16 (d,2H), 3.86 (s,3H), 3.46 (d,3H), 2.47 (d,3H), 2.10 (d,6H).

936 5 8.74 (d,lH), 8.10 (s,1H), 7.48 (m,4H), 5.23 (s,2H), 4.46 (d,lH), 4.35 (d,1H), 3.93 (s,3H), 3.43 (s,3H), 2.33 (s, 3H).

937 # 7.48 (d,lH), 7.46 (s,lH), 7.41 (dd,2H), 7.35 (d,lH), 7.16 (d,2H), 5.15 (ABq, 2H), 3.46 (s,3H), 2.34 (s,3H), 2.18 (s,6H), 1.95 (s,3H).

943 # 7.52-7.56 (m,lH), 7.47-7.51 (m,3H), 7.36-7.42 (m, 2H), 7.21 (d,1H), 3.80 (s,3H), 3.41 (s,3H). 0.22 (s,9H), 0.20 (s,9H).

945 # 7.25-7.7 (m,2H), 7.15 (d,1H), 3.85 (s,3H), 3.4 (s,3H), 2.55 (t,2H).

2.4 (s,3H), 1.55 (m,2H), 1.35 (s,9H), 1.3 (m,4H), 0.9 (t,3H).

946 # 7.9 (s,1H), 7.8 (d,1H), 7.55 (m,2H), 7.4 (m,2H), 7.2 (d,1H), 3.85 (s,3H).

3.4 (s,3H), 2.6 (t,2H), 2.5 (s,3H), 1.6 (m,2H), 1.3 (m,4H), ().9 (t,3H) 947 # 7.82 (s,1H), 7.75 (d,1H), 7.60 (d,1H), 7.58-7.45 (m,4H), 5.18 (dd,2H), 3.47 (s,3H, NHC3), 2.19 (s,3H, CH3).

949 # 7.85 (s,1H), 7.78 (d,1H), 7.60 (d,1H), 7.50-7.30 (m,4H), 5.15 (ABq,2H), 3.48 (s,3H, NCH3), 2.22 (s,3H, ArCH3), 2.19 (s,3H, CH3).

950 # 7.85 (s,1H), 7.80 (d,1H), 7.60 (d,1H), 7.45 (t,1H), 7.40-7.25 (m,3H), 5.18 (ABq,2H), 3.89 (s,3H), 3.41 (s,3H), 2.22 (s,3H), 2.18 (s,3H).

951 # 7.85 (s,1H), 7.78 (d,1H), 7.60 (d,1H), 7.45 (t,1H), 7.15 (d,1H), 7.10 (d,1H), 6.95 (dd,1H), 5.18 ABq,2H), 3.87 (s,3H), 3.42 (s,3H), 2.21 (s,3H).

953 # 7.86 (s,1H), 7.80 (d,1H), 7.60 (d,1H), 7.50 (t,1H), 7.40 (s,1H), 7.25 (d,1H), 7.14 (s,1H), 5.24 (ABq,2H), 3.88 (s,3H), 3.39 (s,3H), 2.41 (s,3H), 2.21 (s,3H).

954 # 7.85 (s, 1H), 7.78 (d,1H), 7.60 (d,1H), 7.50 (t,1H), 7.33 (m,2H), 7.10-7.05 (m,lH), 5.23 (s,2H), 3.84 (s,3H), 3.43 (s,3H), 2.53 (s,3H), 2.17 (s,3H).

955 # 7.49 (d,2H), 7.37-7.26 (m,4H), 5.15 (ABq,2H), 3.89 (s,3H), 3.43 (s,3H), 2.18 (s,3H), 2.15 (s,3H).

956 # 7.48 (d,2H), 7.42 (t,1H), 7.32 (d,1H), 7.15 (d,1H), 6.95 (d,1H), 5.20 (ABq,2H), 3.88 (s,3H). 3.81 (s,3H), 3.43 (s,3H), 2.11 (s,3H) 957 # 7.86 (s,1H), 7.80 (d,1H), 7.60 (d,1H), 7.50-7.40 (m,2H), 7.15 (d,1H).

6.99 (d,lH), 5.22 (ABq,2H), 3.87 (s,3H), 3.81 (s,3H), 3.4' (s,3H).

2.23 (s,3H).

959 # 7.84 (s,1H), 7.78 (d,1H), 7.60 (d,1H), 7.47-7.40 (m,2H), 7.34 (d,1H), 7.18 (t,lH), 5.27 (ABq,2H), 3.88 (s.3H), 3.41 (s,3H), 2.22 (s,3H).

962 87.50 (m,2H), 7.34 (m,4H), 7.20 (m,lH), 5.18 (dd.2H), 3.87 (s,3H), 3.40 (s,3H), 2.18 (s,6H).

964 # 8.74 (d,1H), 8.10 (s,1H), 7.38 (m,4H), 5.27 (d,1H), 5.19 (d,1H), 3.89 (s,3H), 3,43 (s,3H), 2.31 (s,3H), 2.18 (s,3H).

965 # 7.97 (s,1H), 7.82 (m,4H), 7.42 (m,5H), 5.25 (d,1H), 5.17 (d,1H), 3.89 (s,3H), 3.41 (s,3H), 2.32 (s,3H), 2.19 (s,3H).

966 # 7.82 (s,1H), 7.78 (d,1H), 7.59 (d,1H), 7.52-7,38 (m,2H), 7.22 (d,1H), 7.08 (d,1H), 5.33 (s,2H), 3.82 (s,3H), 3.38 (s,3H), 2.14 (s,3H).

967 # 7.87 (s,1H), 7.79 (d,1H), 7.59 (d,1H), 7.45 (t,1H), 7.20 (s,1H), 7.12 (s,1H), 5.16 (d,1H), 5.11 (d,1H), 3.88 (s,3H), 3.40 (s,3H), 2.37 (s,3H), 2.22 (s,3H), 2.14 (s,3H).

971 # 7.87 (s,1H), 7.78 (d,1H), 7.64 (s,1H), 7.60 (d,1H), 7.30-7.20 (m,2H).

7.17 (s,lH), 5.21 (ABq,2H), 3.87 (s,3H), 3.39 (s.3H). 2.21 (s,3H).

0.25 (s,9H).

972 # 7.85 (s,1H), 7.80 (d,1H), 7.68 (s,1H) 7.60 (d,1H), 7.52 (d,1H), 7.50- 7.42 (m,1H), 7.22 (s,1H), 5.23 (ABq,2H), 3.89 (s,3H), 3.40 (s,3H), 3.15 (s,lH), 2.22 (s,3H).

976 # 7.28 (m,6H), 7.02 (m,1H), 5.71 (m,2H), 3.75 (s,3H), 3.40 (s,3H), 2.19 (s, 3H).

982 # 7.83 (br d,1H), 7.75 (d,1H), 7,57 (m,2H), 7.43 (m,3H), 7.17 (d,1H), 5.37 (q,1H), 3.9 (d,3H), 3.42 (d,3H), 2.23 (d,3H), 1.63 (d,3H).

990 [in Me2SO-d6]: 5 8.88-8.95 (m,lH), 8.20-8.29, (m,lH), 7.40- 7.67 (m,4H), 3.82 (s,3H), 3.12 (s,3H).

993 # 7.6 (d,1H), 7.4-7.5 (m,3H), 7.3 (d,1H), 7.2 (d,1H), 6.7 (d,1H), 5.2 (q,2H), 4.9-5.0 (m,lH), 3.89 (s,3H), 3.41 (s,3H), 3.3 (m,lH), 2.8 (m,lH), 2.16 (s,3H), 1.4 (d,3H).

994 # 7.6 (d,lH), 7.4-7.5 (m,3H), 7.3 (d,1H), 7.2 (d,lH), 6.7 (d,lH), 5.2 (d,lH), 5.1 (d,1H), 4.9 (m,lH), 3.47 (s,3H), 3.2-3.3 (m,lH), 2.8 (m,lH), 2.14 (s,3H), 1.4 (d, 3H).

996 # 7.54 (m,1H), 7.41 (m,3H), 7.23 (m,4H), 5.22 (s,2H), 4.69 (m,2H).

3.90 (s,3H), 3.41 (s,3H).

998 # 7.60 (d,lH), 7.50-7.38 (m,2H), 7.20 (d,lH), 4.40 (AB q,2H), 3.92 (s,3H), 3.44 (s,3H), 3.31 (s,3H), 999c 88.8 (s,lH), 8.52 (s,lH). 7.2-7.7 (m,18H), 5.2 (dd,2H), 5.0 (dd,2H).

3.87 (s,3H), 3.84 (s,3H), 3.41 (s,3H), 3.39 (s,3H), 1.92 (s,3H), 1.84 (s,3H).

10OOC # 8.8 (s,lH), 8.58 (s,lH), 7.2-8.0 (m,16H), 4.95-5.15 (m,4), 3,88 (s,3H), 3.85 (s,3H), 3.41 (s,3H), 3.40 (s,3H), 2.02 (s,3H), 1.90 (s,3H).

1010c # 7.5-7.7 (m,2H), 7.4-7.5 (m,2H), 7.2-7.3 (m,lH), 6.9-7.0 (m,2H), 5.15-5.31 (m,2H), 3.77-3.91 (m,3H), 3.0-3.5 (m,5H), 2.52-2.65 (m,lH), 1.24 (m,3H).

1011 # 7.59 (m,2H), 7.50 (m,2H), 6.64 (s,1H), 3.81 (s,3H), 3.40 (s,3H).

1012 # 7.53 (m,1H), 7.34 (m,3H), 6.85 (s,2H), 5.28 (s,2H), 3.94 (s,3H), 3.88 (s,6H), 3.85 (s,3H), 3.44 (s,3H), 2.22 (s,3H).

1024 # 7.44-7.92 (m,6H), 5.53 (s,1H), 3.91 (s,3H), 3.85 (m,2H) 3.69 (m,2H).

3.53 (s,3H), 1.29 (m,6H).

a 1H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (dt)-doublet of triplets, (br)-broad, (br s)-broad singlet, (br d)-broad doublet, (br m)-broad multiplet, (AB q)-AB pattern quartet. Coupling constants (indicated by J) are in Hertz.

b Partial NMR.

c Mixture of E and Z isomers.

BIOLOGICAL EXAMPLES OF THE INVENTION 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 TremR 014 (polyhydric alcohol esters). The resulting test suspensions were then used in Tests A-F. Spraying these 200 ppm test suspensions to the point of run-off on the test plants is the equivalent of a rate of 500 g/ha.

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 200C 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 PU'.(itlicI 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 Pyricularici 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 300C 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 Phytophtlzora infestans (the causal agent of potato and tomato late blight) and incubated in a saturated atmosphere at 200C 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 200C for 24 h, moved to a growth chamber at 20°C for 6 days, and then incubated in a saturated atmosphere at 200C 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 B()lr'ii.\- cinerea (the causal agent of gray mold on many crops) and incubated In a saturated atmosphere at 200C for 48 h, and moved to a growth chamber at 20°C for 5 days. after which disease ratings were made.

Results for fungicide Tests A-F are given in Table A for compounds of Formulae IA and IB. In the table, a rating of 100 indicates 100% disease control and a rating of 0 indicates no disease control (relative to the controls). A dash (-) indicates no test results. ND indicates disease control not determined due to phytotoxicity.

Table A Cmpd No. Test A Test B Test C Test D Test E Test F 187 100 96 74 75 100a 88 239 99 97 90 73 5a 0 263 35 99 32 77 43a 264 91 97 0 86 94a 44 265 35 93 0 0 96a 266 0 93 0 86 46a 267 0 97 0 77 30a 268 35 97 32 77 48a 269 100 99 53 93 68a 44 270 61 97 0 77 69a 0 271 61 97 0 64 41a 272 61 93 0 93 82a 273 77 85 0 77 79 279 60 84 32 63 70 92 280 100a 99a 39a 31b 94a 287 100 100 86 86 94a 288 99 100 74 76 99a 32 289 99 100 53 63 100a 0 290 99 100 53 86 100a 0 291 99 100 97 25 87a 0 292 100 100 53 86 63a 293 100 100 86 93 100a 68 294 99 99 91 76 100a 45 295 99 100 74 46 99a 82 296 100 100 86 93 100a 5 297 55 65 53 0 96a 306 99 85 32 0 0 5a 5a 309 100 100 97 25 99a 0 310 99 99 74 63b 96a 311 - - 312 73 85 53 25 99a 317 86 85 0 91 2a 0 320 99 97 86 100 91a 0 321 100 99 100 96 97a 322 99 93 53 91 78a 323 99 100 53 96 99a 42 324 99 99 53 91 86a 42 325 100 99 86 ND 100a 42 326 99 100 86 72b 97a 0 327 36 93 0 91 36a 0 328 61 93 0 91 57c 0 329 99 99 86 96 100a 66 330 0 93 32 96 94a 0 331 0 85 32 83 5a 0 332 61 93 32 91 57a 333 95 93 53 96 94a 66 334 100 97 91 83 61a 94 335 100 99 86 96 94a 337 99 97 0 96 100a 68 341 100 100 94 100 99a 94 342 100 100 100 36 100a 98 343 100 99 97 91 100a 68 344 100 99 100 96 94a 345 100 99 53 ND 100a 68 349 58 93 0 44 61a 39 353 98d 97d 0d 75d 36a 65d 354 99 100 0 ND 90a 0 358 99 100 94 92 100a 361 100 97 53 22 48a 0 363 100 100 74 70 30a 364 99 97 74 53 23a 88 365 98 97 53 53 43a 366 99 97 53 82 15a 3X 367 99 97 53 85 5 XI 368 99 93 53 3 10a XX 369 97 100 53 ND 100b 0 372 57 94 0 26 5a 0 381 74 94 0 61 15a 69 387 96 97 53 72 85a 0 393 0 86 0 20 - () 394 0 86 0 20 () 395 100 100 91 20 7 396 99 99 0 97 67a 0 397 99 100 0 77 58a 405 89 86 0 57 26a 410 50 94 0 57 21a 0 411 50 99 0 91 11a 0 412 93 94 53 0 19a 7 413 100 100 94 72 100b 0 425 61 94 0 60 11a 0 427 95 97 53 74 45a 0 428 36 94 74 74 2a 445 99 86 0 96 100b 446 100 100 53 84 45a 81 449 0 68 74 15 () 452 99 100 85 75 5a 31 453 99 99 85 75 16a 31 454 38 67 50 99 76a 0 455 0 0 0 54 18 92 457 100 93 73 91 89a 0 458 63 85 73 91 55 0 459 100 93 93 91 100a 0 462 99 93 73 91 87a 465 0 85 0 0 23a 466 0 26 0 82 6a 467 100 100 90 NDb 100a 0 474 99 97 85 99 100a 0 475 100 99 85 91 100a 0 476 77 26 50 91 24a 477 99 93 50a 91 100a 0 478 98 100 97 92 82a 22 485 99 97 60 95 94a 97 486 73a 48a 14b 13b 67a 487 73a 70C 81b 32b 74a 488 98 99 74 62 63a 77 489 99 99 74 95 56a 0 490 99 99 74 28 72a 0 491 98 99 93 62 2a 87 492 91 99 74 99 28a 97 493 95 99 74 0 77 494 91 94 28 83 32a 92 495 97 99 83 95 57a 32 496 98 99 0 0 10a 99 497 86 97 28 95 17a 87 500 100 100 94 92 100a 0 501 100 100 85 16 70a 0 507 99 99 74 100 100a 92 508 100 100 74 95 88a 92 509 100 100 90 99 100a 0 510 99 100 85 92 79a 511 99 100 90 73 34a 22 513 91 67 30 16 21a 85 515 100 100 97 99 100a 0 516 91 100 73 84 60a 85 517 99 100 90 92 44a 22 518 100 100 90 100 9la X.5 519 60 93 51 16 () 520 100 100 90 92 7a 55 526 84 97 32 65 62a 96 527 84 93 0 22 70a 0 528 56 99 53 89 - 81 530 99 100 51 40 11a 22 531 94d 97d 32d 65d - ggd 532 98 99 86 79 12a 533 56 93 0 95 42a 98 534 26 93 32 89 16a 99 535 84 99 0 89 40a 98 536 84 97 32 89 59a 99 537 100 100 53 79 9X 538 100 100 91 95 100a 99 539 100 99 53 79 97a 540 96 99 53 ND 100a 0 541 94 99 32 ND 95a 0 547 86 86 31 94 5a 0 548 91 94 94 100 58a 42 549 98 99 90 87 47e 42 550 100a 99a 59b 100a 554 100a 99a 87b - 98a 555 100a 99a 88b - 100a 556 99 97 74 100 72a 42 557 95 97 52 94 88a XI 561 90 94 53 84 1 1a 9X 562 100 100 99 91 100e 0 563 99 100 86 91 0 564 100 100 86 58 - 0 567 100 100 90 29 67a 0 568 98 94 86 81 3a 569 0 68 0 29 14a 0 572 99 100 74 65 97a 0 573 94 94 0 0 13a 0 574 100 94 74 25 0 577 97 97 0 0 16a 582 57 - 0 0 656 95 97 32 82 10 79 657 62 85 0 70 44a 658 86 93 0 31 44 3X 659 37 85 0 31 10a 38 660 77 93 32 70 29a 79 661 77 93 32 3 26a 38 662 86 85 32 3 37a 79 663 95 97 0 ND 66b 0 664 94 97 53 61 35a 46 665 98 94 53 43 - 7 666 99 99 53 20 - 7 667 99 100 53 20 99a 0 668 - - - - 669 91 94 0 20 100a 82 670 100 86 53 20 - 7 671 86 94 53 60 39a 67 672 100 100 96 85 94a 0 673 99 99 90 ND 97a 0 674 99 100 90 20 75a 60 675 100 100 98 ND 100a 0 676 100 100 94 - 100a 0 677 91a 99 100 91 100a 678 100 100 90 ND lIlly 679 100 100 93 91 100a 0 680 100 99 97 62 86a 685 95 86 74 0 19a 61 690 99 99 74 0 10a 691 99 94 60 95 59a 87 692 99 99 74 100 96a 61 693 91 99 83 100 100a 0 694 86 94 83 83 63a 92 695 86 94 74 100 41a 0 699 100 100 93 ND 100a 0 700 98 99 0 ND 100a 0 704 100 100 100 - 100a O 705 99a 99a 71b 62a 706 100 100 94 ND 100a 0 708 91 93 52 16 79a 0 709 98 97 0 63 0 712 91 97 31 78 97a 48 713 91 86 90 100 24a 714 84 86 94 14 24a 0 716 99 99 91 - 100a 0 717 100 99 91 ND 100a 0 719 100 100 90 1 39a 0 720 99 94 53 25 Oa 47 721 99 94 32 25 94a 82 722 100 99 74 76 73a 723 100 100 91 76 84a 0 724 100 100 94 - 100a 0

725 100 99 91 76 100a 47 727 99 99 90 23 86a 83 728 99 100 90 23 91a 0 729 99 100 90 86 100a 0 730 100 99 90 0 50a 70 731 100 100 90 63 100a 0 a Compound was tested at 10 ppm (equivalent to 25 g/ha).

b Compound was tested at 40 ppm (equivalent to 100 g/ha).

c Compound was tested at 2 ppm (equivalent to 5 g/ha).

d Compound was tested at 100 ppm (equivalent to 250 g/ha).

Results for arthropodicide Tests G-L are given below for compounds of Formulae I, IA and IB.

TEST G Fall Armyworm Test units, each consisting of a H.I.S. (high impact styrene) tray with 16 cells were prepared. Wet filter paper and approximately 8 cm2 of lima bean leaf was placed into twelve of the cells. A 0.5-cm layer of wheat germ diet was placed into the four remaining cells. Fifteen to twenty third-instar larvae of fall armyworm (Spodoptera frugiperda) were placed into a 230-mL (8-ounce) plastic cup. Solutions of each of the test compounds in 75:25 acetone-distilled water solvent were sprayed into the tray and cup. Spraying was accomplished by passing the tray and cup on a conveyer belt dh-ectl beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.138 kilograms of active ingredient per hectare (about 0.13 pounds per acre) at 2()7 kPi (30 p.s.i.). The insects were transferred from the 230-mL cup to the H.l.S. tray (one insect per cell). The trays were covered and held at 27°C and 50% relative humidily tOI 48 hours, after which time readings were taken on the twelve cells with lima bean lea'-.e.

The four remaining cells were read at 6-8 days for delayed toxicity. Of the compounds tested, the following gave control efficacy levels of 80% or greater: 313, 329, 404, 4')3« 538, 543, 546, 672, 673, 674, 677, 678, 679, 680, 688, 699, 701, and 703.

TEST H Southern Corn Rootworm Test units, each consisting of a 230-mL (8-ounce) plastic cup containing a 6.5-cm2 (1-square-inch) plug of a wheatgerm diet, were prepared. The test units were sprayed as described in TEST G with individual solutions of the test compounds. After the spray on the cups had dried, five second-instar larvae of the southern corn rootworm (Diabrotica

undecimpunctata howardi) were placed into each cup. The cups were held at 27°C and 50% relative humidity for 48 hours, after which time mortality readings were taken. The same units were read again at 6-8 days for delayed toxicity. Of the compounds tested, the following gave control efficacy levels of 80% or greater: 11*, 207, 304, 313, 341, <BR> <BR> <BR> <BR> 345, 403, 404, 413, 442, 443, 445, 451, 479, 500, 506, 514, 515, 537, 542, 546, 550, <BR> <BR> <BR> <BR> <BR> <BR> 675, 677, 679, 680, 682, 683, 684, 687, 688, 689, 699, 700, 701, 703, 704, 705, 706, 715, and 717.

* Tested at 0.55 kg/ha.

TEST I Aster Leafliopper Test units were prepared from a series of 350-mL (1 2-ounce) cups. each containing oat (Avena sativa) seedlings in a 2.5-cm (l-inch) layer of sterilized soil The test units were sprayed as described in TEST G with individual solutions of the Lesl compounds. After the oats had dried from the spraying, 10 to 15 adult aster leafhoppers (Mascrosteiesfascfrons) were aspirated into each of the cups. The cups were covered with vented lids and held at 270C and 50% relative humidity for 48 hours, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 80% or higher: 345, 672, 679, and 715.

TEST J Contact Test Against Black Bean Aphid Individual nasturtium leaves were infested with 10 to 15 aphids (all morphs and growth stages of Aphisfabae) and sprayed with their undersides facing up as described in TEST G. The leaves were then set in 0.94-cm (3/8-inch) diameter vials containing 4 mL of sugar solution (approximately 1.4 g per liter) and covered with a clear plastic 29-mL (l-ounce) cup to prevent escape of the aphids that drop from the leaves. The lest units were held at 270C and 50% relative humidity for 48 hours, after which time mortality readings were taken. Of the compounds tested, the following give mortality levels of 80% or higher: 187, 272, 288, 304, 321, 325, 329, 342, 343, 348, 4ü(), 413.

515, 538, 550, 554, 674, 679, and 688.

TEST K Two-Spotted Spider Mite Pieces of kidney bean leaves, each approximately 6.5 cm2 (1 square inch) in area, that had been infested on the undersides with 25 to 30 adult mites (Tetranychus urticae), were sprayed with their undersides facing up on a hydraulic sprayer with a solution of the test compound in 75:25 acetone-distilled water solvent. Spraying was accomplished by passing the leaves, on a conveyor belt, directly beneath a flat fan hydraulic nozzle which

discharged the spray at a rate of 0.138 kilograms of active ingredient per hectare (about 0.13 pounds per acre) at 207 kPa (30 p.s.i.). The leaf squares were then placed underside-up on a square of wet cotton in a petri dish and the perimeter of the leaf square was tamped down onto the cotton with forceps so that the mites could not escape onto the untreated leaf surface. The test units were held at 270C and 50% relative humidity for 48 hours, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 80% or higher: 146, 162, 187, <BR> <BR> <BR> 239,247,296,306,321,325,329,343,345,373,378,467,490,493,500, 515,531, <BR> <BR> <BR> <BR> <BR> <BR> 532, 537, 538, 550, 670, 672, 673, 674, 675, 676, 677, 679, 680, 681, 683, 690, 693, <BR> <BR> <BR> <BR> <BR> <BR> 699,701,715, and 717.

The same units were held an additional 5 days and read for larvicide/ovicide mortality and/or developmental effects. Of the compounds tested, the following gave activity levels of 80% or higher: 15*, 187, 343, 420, 466, 520, 534, 535,536.540,541.

548, 550, 554, 682, 689, and 693.

* Tested at 0.55 kg/ha.

TEST L Larval two-Spotted Spider Mites (Tetranychus urticae) Solutions of the test compounds were prepared by dissolving in a minimum of acetone and then adding water containing a wetting agent until the concentration of the compound was 50 ppm. Two-week old red kidney bean plants infested with two-spotted spider mites eggs were sprayed to run-off (equivalent to 28 g/ha) with the test solution using a turntable sprayer. Plants were held in a chamber at 250C and 50% relative humidity. Of the compounds tested, the following gave larvicide/ovicide activity of 80% or higher seven days after spraying: 187, 466, 670, 674, 675, and 677.

Specific compounds of Formula II which are useful as intermediates for the preparation of the fungicides and arthropodicides of Formula I where Y is oxygen are described in Index Tables N and 0. The abbreviation "Ex." stands for "Example" and is followed by a number and step indicating in which example step the intermediate is prepared.

INDEX TABLE N 43 OH X 90 wherein R3a is H or R3 N-N CH3 Cmpd No. X R3a m.p. (°C) 733 Ex. 1 Step C Cl H solid 734 Ex. 1 Step D CH3O H solid 735 Ex. 22 Step D CH30 6-CH3 194-191) 736 Ex. 22 Step C Cl 6-CH3 175-178 737 CH3O 4-CH3O 163-165 738 Cl 4-CH3O 192-194 979 MeO 6-CH3S 185-190 980 MeO 3-CH3 195-197 *See Index Table 0 for 1H NMR data.

INDEX TABLE O Cmpd No. 1H NMR Data (CDCl3 solution unless indicated otherwise)a 733 # 8.18 (s,lH), 7.11 (t,2H), 6.91 (t,lH), 6.76 (d,lH), 3.56 (s,3R).

734 # 8.40 (br s,lH), 7.20 (m,2H), 7.03 (d,1H), 6.94 (t,lH), 4.00 (s,3H), 3.48 (s,3H).

a H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (m)-multiplet, (br s)-broad singlet.