NZ310884A

NZ310884A - Arthropodicidal and fungicidal cyclic amides

Info

Publication number: NZ310884A
Application number: NZ310884A
Authority: NZ
Inventors: Richard James Brown; Dominic Ming-Tak Chan; Michael Henry Howard; Thomas Paul Selby; Dilon Jancey Daniel; David Alan Clark
Original assignee: Du Pont
Priority date: 1995-06-20
Filing date: 1996-06-13
Publication date: 1999-04-29
Also published as: HUP9901228A2; AU6177096A; CZ394097A3; PL324291A1; JPH11508257A; KR19990028230A; HUP9901228A3; MX9710259A; WO1997000612A1; BR9609001A; IL122670A0; ZA965196B; EP0836384A1

Description

<div class="application article clearfix" id="description"> New Zealand Paient Spedficaiion for Paient Number 310884 # New Zealand No. 310884 International No. PCT/US96/10326 TO BE ENTERED AFTER ACCEPTANCE AND PUBLICATION Priority dates: 20.06.1995; Complete Specification Filed: 13.06.1996 Classification:^) A01N43/00 Publication date: 29 April 1999 Journal No.: 1439 Title of Invention: Arthropodicidal and fungicidal cyclic amides Name, address and nationality of applicant(s) as in international application form: E. I. DU PONT DE NEMOURS AND COMPANY, 1007 Market Street, Wilmington, Delaware 19898, United States of America NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION WO 97/00612 310884 PCT/US96/10326 TITLE ARTHROPODICIDAL AND FUNGICIDAL CYCLIC AMIDES BACKGROUND OF THE INVENTION This invention relates to certain cyclic amides, their A7-oxides, agriculturally 5 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 10 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, 15 household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds 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: R4 A—N \ 20 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 25 double bond is attached to A; W is O or S; X is OR1; S(0)mR1; or halogen; R1, R-, and R^ are each independently, in part, H or Cj-Cg alkyl; WO 97/00612 PCT/US96/10326 R3 and R4 are each independently, in part, H; halogen; cyano; nitro; C]-Cg alkvl; CpCg haloalkyl; CrC6 alkoxy; or CrC6 haloalkoxy; Y is, in pari, -O-; -CR6=CR6-; -C=C~; -CHR60-; -OCHR6-; -CHR60-N=CfR7)-; -(R7)C=N-OCH(R6)-; -C(R7)=N-0-; -0-N=C(R7)-; or a direct bond; 5 R6 is independently H or C1-C3 alkyl; R7 is, in part, H; Cj-Cg alkyl; C]-C6 haloalkyl; or C]-Cg 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; 10 R14 is H; halogen; Cj-Cg alkyl; Cj-Cg haloalkyl; Cr-C^ alkenyl; C2-Cg haloalkenyl; C2"Cg alkynyl; C2-Cg haloalkynyl; or C3-C6 cycloalkyl; and m is 0, 1 or 2. This publication does not disclose use of the compounds as arthropodicides. Furthermore, this publication does not disclose compounds where the optional 15 substituents on Z are themselves substituted with C^-Cg alkenyl, C2~Cg haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, CrC4 alkylthio, C]-C4 haloalkylthio, Cj-C4 alkylsulfinyl, Q-C4 haloalkylsulfinyl, Cj-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C3-C6 alkenylthio, CyC^ haloalkenylthio, or SF5. SUMMARY OF THE INVENTION 20 This invention involves compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof: X^fyw A—N R2 I wherein 25 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 30 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 WO 97/00612 PCT/US96/10326 bicvclic 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 5 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(=0) 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 10 ring members, each aromatic heterocyclic ring system optionally substituted with one of R3, R4, or both R3 and R4; A is 0;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 15 floating double bond is attached to A; W is O; S; NH; N(CrC6 alkyl); or NO(CrC6 alkyl); X is H; OR1; SCO^R1; halogen; Cj-Cg alkyl; Cj-Cg haloalkyl; C3-C6 cycloalkyl; cyano; NH2; NHR1; N(CrC6 alkyl)R]; NH(CrC6 alkoxy); or N(C]-C6 alkoxy)R1; 20 R1 is Cj-Cg alkyl; C]-Cg haloalkyl; C2*Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C3*Cg cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxy carbonyl; R2 is H; Cj-Cg alkyl; Cj-C6 haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 25 alkoxycarbonyl; hydroxy; CpC2 alkoxy; or acetyloxy; R3 and R4 are each independently halogen; cyano; nitro; hydroxy; Cj-Cg alkyl; Cj-Cg haloalkyl; C2*C6 alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-C6 haloalkynyl; CpCg alkoxy; Cj-Cg haloalkoxy; C2-C6 alkenyloxy; C2-Cg alkynyloxy; Ct-C6 alkylthio; Cj-C6 alkylsulfmyl; CrC6 alkylsulfonyl; formyl; 30 ^-Cg alkylcarbonyl; C2-Cg alkoxycarbonyl; NH2CXO); (CrC4 alkyl)NHC(O); (CrC4 alkyl)2NC(0); Si(R25)3; Ge(R25)3; (R25)3Si-CsC-; 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 35 can be taken together as C3-C5 alkylene, C3-C5 haloalkylene, C3-C5 WO 97/00612 PCT/US96/10326 4 alkenylene or C3-C5 haloalkenylene each optionally substituted with 1-2 C1-C3 alkyl; R5 is H; Cj-Cg alkyl; C| -C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C(, cycloalkyl; C1-C4 alkylcarbonyl; or C2-C4 5 alkoxycarbonyl; Y is -O-; -S(0)n-; -NR'5-; -C(=0)-; -CHfOR^)-; -CHR6-; -CHR6CHR6-; -CR6=CR6-; -C=C-\ -CHR15Os -OCHR15-; -CHR15S(0)n-; -S(OjnCHR15-; -CHR150-N=C(R7)-; -(R7)C=N-OCH(R15)-; -C(R7)=N-0-; -0-N=C(R7)-; -CHR150C(=0)N(R15)-; -CHR15OC(=S)N(R15)-; -CHR150C(=0)0-; 10 -CHR150C(=S)0-; -CHR150C(=0)S-; -CHR15OC(=S)S-; -CHR15SC(=0)N(R15)-; -CHRi5SC(=S)N(R15)-; -CHRI5SC(=0)0-; -CHR15SC(=S)0-; -CHR15SC(=0)S-; -CHR^SC^SJS-; -CHR15SC(=NRl5)S-;-CHRI5N(R15)C(=0)N(R15)-; -CHR1 SO-NCR^C^OMR15)-; -CHR150-N(R15)C(=S)N(R1^)-; 15 -CHR'l50-N=C(R7)NR15-; -CHR150-N=C(R7)0CH2-; -CHR150-N=C(R7)-N=N-; -CHR150-N=C(R7)-C(=0)-; -CHR150-N=C(R7)-C(=N-A2-Z* )-A1 -; -CHR150-N=C(R7)-C(R7)=N-A2-A3-;-CHR150-N=C(-C(R7)=N-A2-Z1)-; -CHR150-N=C(R7)-CH20-; -CHR150-N=C(R7)-CH2S-; 20 -0-CH2CH20-N=C(R7)-; -CHR150-C(R15)=C(R7)-; -CHR150-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(=G)-; -CHR6-C(=W1)-A1-; -CHR6CHR6-C(=W1)-A1-; -CR6=CR6-C(=Wl)-A1-; -C=C-C(=W1)-A1-; -N=CR6-C(=W1)-A1-; or a 25 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 is O or S; 30 A1 is O; S; NR15; or a direct bond; A2 is O; NR15; or a direct bond; A3 is -C(=0)-; -S(0)2-; or a direct bond; each R6 is independently H; 1-2 CH3; C2-C3 alkyl; CpC3 alkoxy; C3-C6 cycloalkyl; formylamino; C2-C4 alkylcarbonylamino; C2-C4 35 alkoxycarbonylamino; NH2C(0)NH; (CpC3 alkyl)NHC(0)NH; WO 97/00612 PCT/US96/10326 (C1-C3 alkyl)2NC(0)NH; N(C|-C3 alkyl)2; pipcridinyl; morpholinyl; 1-2 halogen; cyano; or nitro; each R7 is independently H; Cj-Cg alkyl; C|-Ch haloalkyl; CpCg alkoxy; CpCg haloalkoxy; CrC6 alkyhhio; C]-C6 alkylsulfinyl; C]-C6 alkylsulfonyl; CpC6 5 haloalkylthio; CrC6 haloalkylsulfinyl; C]-C6 haloalkylsulfonyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3~Cg cycloalkyl; CVC4 alkylcarbonyl; C2-C4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy; amino; NH(Cj-Cg alkyl); NCCj-Cg alky])2; or morpholinyl; each Z is independently selected from; 10 i) Cj-Cjo alkyl, C2-Cjo alkenyl, and C2-Cjq alkynyl each substituted with R9 and optionally substituted with one or more R10; ii) C3-C8 cycloalkyl, C3*Cg 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 15 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 20 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 25 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(=0) and S(0)2, and any remaining rings as aromatic carbocyclic rings, each multicyclic ring system substituted with R9 and optionally substituted with 30 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-, -0-, and -S(0)p-; 35 R8 is H; 1-2 halogen; Cj-Cg alkyl; Cj-Cg haloalkyl; Cj-Cg alkoxy; C]-Cg haloalkoxy; C2-Cg alkenyl; C2-C6 haloalkenyl; C2-Cg alkynyl; CrC6 WO 97/00612 PCT/US96/10326 m 6 alkylthio; CpCg haloalkylthio; Cj-Cg alkylsulfinyl; C|-C6 alkylsulfonyl; C3-Cg cycloalkyl; C3-Cg alkenyloxy; C02(C]-Cg alkyl); NH(Cj Cg alkyl); N(CrCg alkyl)2; cyano; nitro; SiR19R20R21; or GeR19R20R21; is H; 1-2 halogen; CrCg alkyl; C]-Cg haloalkyl; C]-Cg alkoxy; Cj-C6 5 haloalkoxy; C2-Cg alkenyl; Co-C^ haloalkenyl; C2~Cg alkynyl; Cj-Cg alkylthio; CpCg haloalkylthio; Cj-Cg alkylsulfinyl; Cj-Cg alkylsulfonyl; C3*Cg cycloalkyl; C3*Cg alkenyloxy; C02(C]-C6 alkyl); NH(C]-Cg alkyl); N(C]-C6 alkyl)2; -C(R18)=NOR17; cyano; nitro; SF5; SiR22R23R24. or GeR22R23R24; or R9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, 10 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; Cj-C4 alkyl; C1-C4 haloalkyl; Cj-C4 alkoxy; nitro; or cyano; or when R9 and an R10 are attached to adjacent atoms on Z, R9 and said adjacently 15 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)-, -0-N=C(R7)-, -0-CH2CH20-N=C(R7)-, 20 -CHR150-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-; -CH20-; -SCH2-; -CH2S-; -N(R16)CHr; or -CH2N(R16)-; each CH2 group of said J optionally substituted with 1 to 2 25 CH3; R11 and R12 are each independently 1-2 halogen; C1-C4 alkyl; Cj-C4 haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-C6 haloalkynyl; C2-C6 alkoxyalkyl; C2-C6 alkylthioalkyl; C3-C6 alkoxyalkynyl; C7-C10 tetrahydropyranyloxyalkynyl; benzyloxymethyl; CpC4 alkoxy; CrC4 30 haloalkoxy; C3-C6 alkenyloxy; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy; C3-C6 haloalkynyloxy; C2-C6 alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; C]-C4 . Jkylthio; C1-C4 haloalkylthio; Cj-C4 alkylsulfinyl; C]-C4 haloalkylsulfinyl; CrC4 alkylsulfonyl; CpC4 haloalkylsulfonyl; C3*Cg alkenylthio; CyC^ haloalkenylthio; C2-Cg 35 alkylthioalkylthio; nitro; cyano; thiocyanato; hydroxy; N(R2^)2; SF5; Si(R25)3; Ge(R25)3; (R25)3Si-C=C-; OSi(R25)3; OGe(R25)3; C(=Q)R26; WO 97/00612 PCT/US96/10326 Q=S)R26; C(=0)0R26; C(=S)OR2t1; C(=0)SR26; C(=S)SR26; C(=0)N(R26)2; C(=S)N(R26)2; 0C(=0)R26; OC(=S)R26; SC(=0)R26; SC(=S)R26; N(R26)C(=0)R26; N(R26)C(=S)R26; OC(=O)0R27; 0C(=0)SR27; 0C(=0)N(R26)2; SC(=0)0R27; SC(=0)SR27; S(0):0R26; 5 S(0)2N(R26)2; 0S(0)2R27; N(R26)S(0)2R27; or phenyl, phenoxy, benzyl. benzyloxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted with halogen, Cj-C.} alkyl. C1-C4 haloalkyl, Cj-C4 alkoxy, C]-C4 haloalkoxy, nitro or cyano; each R13 is independently H; Cj-Cg alkyl; Cj-C6 haloalkyl; or phenyl optionally 10 substituted with halogen, C]-C4 alkyl, Cj-C4 haloalkyl, Cj-C4 alkoxy, Cj-C4 haloalkoxy, nitro or cyano; R14 is H; halogen; Cj-Cg alkyl; Cj-C6 haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; or C3-C6 cycloalkyl; each R15 is independently H; Cj-C3 alkyl; C3-Cg cycloalkyl; or phenyl or benzyl, 15 each optionally substituted on the phenyl ring with halogen, CJ-C4 alkyl, C]-C4 haloalkyl, C1-C4 alkoxy, C]-C4 haloalkoxy, nitro or cyano; or when Y is -CHRI5N(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 -CHR150-N=C(R7)NR15-, R7 and the adjacently attached R15 can be 20 taken together as -CH2-(CH2)S-; -0-(CH2)s-; -S-(CH2)s-; or -N(Cj-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; 25 R16, R17, and R18 are each independently H; Cj-C3 alkyl; C3-C6 cycloalkyl; or phenyl optionally substituted with halogen, C]-C4 alkyl, Cj-C4 haloalkyl, C]-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; R19, R20, R21, R22, R23, and R24 are each independently Cj-C6 alkyl; C2-C6 alkenyl; C j-C4 alkoxy; or phenyl; 30 each R25 is independently CpC4 alkyl; C]-C4 haloalkyl; C2-C4 alkenyl; Cj-C4 alkoxy; or phenyl; each R26 is independently H; Cj-Cg alkyl; Cj-Cg haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, CrC4 35 alkyl, Cj-C4 haloalkyl, CpC4 alkoxy, Cj-C4 haloalkoxy, nitro or cyano; % 8 each R27 is independently C|-C$ alkyl; Cj-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; Co-C^ alkynyl; C2-C$ haloalkynyl; C3*C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C1-C4 alkyl, CrC4 haloalkyl, CrC4 alkoxy, CrC4 haloalkoxy, nitro or cyano; 5 m, n and p are each independently 0, 1 or 2; r is 0 or 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 10 compound of Formula I including all geometric and stereoisomers, /V-oxides, and agriculturally suitable salts thereof, provided that: (i) when E is 1,2-phenylenc optionally substituted with one of R3, R4, or both R3 and R4; X is OR1, SCOmR1 or halogen; Y is -O-, -S(0)n-, -NR15-, -C(=0)-,-CH(0R15)-, -CHR6-, -CHR6CHR6-, -CR6=CR6-, -C=C-, 15 -CHRlsO-, -OCHR15-, -CHR15S(0)n-, -S(0)nCHR15-, -CHR150-N=C(R7)-, -(R7)C=N-OCH(R15)-, -C(R7)=N-0-, -0-N=C(R7)-, -CHR150C(=0)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 20 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(0)n-, -C(=0)-, -CHR6-, -CHR^HR6-, -CR6=CR6-, -OC-, -OCHR15-, -S(0)nCHR15- or a direct bond; then Z is other than Cj-Cjq alkyl, C2-C]0 25 alkenyl or C2-C1() alkynyl each substituted with R9 and optionally substituted with one or more R10; and (iii) when E is a naphthalene ring optionally subsdtuted with one of R3, R4, or both R3 and R4; R3 or R4 is Si(R25)3 or Ge(R25)3; and Y is -S(0)n-, -C(=0)-, -CsC- or a direct bond; then Z is other than phenyl substituted with R9 and 30 optionally,substituted with one or more R10; and INTELLECTUAL PROPERTY OFFICE OF N.Z. 2 2 FEB 1999 RECEIVED (IV) when E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; W is 0; G is C; A is NR5 with the floating double bond attached to G; X is OR1, and R1 is C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C4 alkylcarbonyl or C2-C4 alkoxy carbonyl; then Y-Z is other than CrC10 alkyl or (VC-,0 alkoxy. 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 al! geometric and stereoisomers, /V-oxides, and agriculturally suitable salts thereof, and agricultural compositions containing them and their use as fungicides and arthropodicides: INTELLECTUAL PROPERTY OFFICE | Df N.Z. 1/2/99cfop552.spe,- 203 - 2 2 FEB 1999 RECEIVED WO 97/00612 PCT/US96/10326 -/vw A — N \ R2 IA wherein E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; A is O or N; 5 G is C or N; provided that wiien G is C, then A is O 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; Wis O; X is OR1; 10 R1 is Cj-C3 aJkyJ' R2 is H or C- C- 'okyl; R3 and R4 are each independently halogen; cyano; nitro; Cj-Cg alkyl; CrC6 haloalkyl; Cj-Cg alkoxy; or Cj-Cg haloalkoxy; Cj-Cg alkylsulfonyl; C2*Cg alkylcarbonyl; C2~C6 alkoxycarbonyl; (Ci-C4 alkyl)NHC(O); 15 (C1-C4 alkyl)2NC(0); benzoyl; or phenylsulfonyl; Y is -0-; -S(0)n-; -NR15-; -C(=0)-; -CH(OR15)-; -CH2-; -CH2CH2-; -CH=CH-; -OC-; -CH2O-; -OCH2-; -CH2S(0)n-; -S(0)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 20 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; Cj-Cg alkyl; Cj-Cg haloalkyl; CpCg alkoxy; Cj-Cg haloalkoxy; 25 QrCg alkenyl; C2~Cg haloalkenyl; C2*Cg alkynyl; C]-Cg alkylthio; Cj-Cg haloalkylthio; Cj-Cg alkylsulfinyl; Cj-Cg alkylsulfonyl; C^-Cg cycloalkyl; C3-C6 alkenyloxy; C02(C,-C6 alkyl); NH(CrC6 alkyl); N(CrC6 alkyl)2; -C(R18)=N0R17; cyano; nitro; SF5; SiR22R23R24; or GeR22R23R24; or R9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, 30 furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one WO 97/00612 PCT/US96/10326 10 of R11, R'-, or both R11 and R12; provided that when Z is pvrazinyl, then R9 is other than H or C j-C6 haloalkyl; each R10 is independently halogen; CrC4 alkyl; CrC4 haloalkyl; CrC4 alkoxy; nitro; or cyano; or 5 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 -0CH2CH20-; each CH2 group of said taken together R9 and R1® optionally substituted with 1-2 halogen; R11 and R12 are each independently 1-2 halogen; Cj-C4 alkyl; CJ-C4 haloalkyl; 10 Co-Cg alkenyl; C2-C6 haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C2-C6 alkoxvalkyl; C2-Cg alkylthioalkyl; C3-Cg alkoxyalkynyl; C7-Cjo tetrahydropyranyloxyalkynyl; benzyloxymethyl; CpC4 alkoxy; C]-C4 haloalkoxy; C3-Cg alkenyloxy; C3-Cg haloalkenyloxy; C3-Cg alkynyloxy; C3-C6 haloalkynyloxy; C2-Cg alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; 15 C2-Cg alkylthioalkoxy; C]-C4 alkylthio; C1-C4 haloalkylthio; C]-C4 alkylsulfinyl; CrC4 haloalkylsulfinyl; C1-C4 alkylsulfonyl; C1-C4 haloalkylsulfonyl; C3-C6 alkenylthio; C3-C6 haloalkenylthio; C2-Cg 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(=0)R26; 20 C(=S)R26; C(=0)0R26; C(=S)OR26; C(=0)SR26; C(=S)SR26; C(=0)N(R26)2; C(=S)N(R26)2; 0C(=0)R26; OC(=S)R26; SC(=0)R26; SC(=S)R26; N(R26)C(=0)R26; N(R26)C(=S)R26; 0C(=0)0R27; 0C(=0)SR27; 0C(=0)N(R26)2; SC(=0)0R27; SC(=0)SR27; S(0)20R26; S(0)2N(R26)2; 0S(0)2R27; N(R26)S(0)2R27; or phenyl, phenoxy, benzyl, 25 benzyloxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted with halogen, C1-C4 alkyl, Cj-C4 haloalkyl, C]-C4 alkoxy, C]-C4 haloalkoxy, nitro or cyano; R15 is H; C1-C3 alkyl; or cyclopropyl; R17 and R18 are each independently H; Cj-C3 alkyl; C3-Cg cycloalkyl; or phenyl 30 optionally substituted with halogen, Cj-C4 alkyl, CrC4 haloalkyl, C1-C4 alkoxy, C]-C4 haloalkoxy, nitro or cyano; r22, r23^ and r24 are each independently Cj-Cg alkyl; C2-Cg alkenyl; Cj-C4 alkoxy; or phenyl; each R25 is independently C]-C4 alkyl; C]-C4 haloalkyl; C2-C4 alkenyl; C]-C4 35 alkoxy; or phenyl; 1 each R26 is independently H; Cj-C6 alkyl; Cj-Cg haloalkyl; C2-Cg 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, Cj-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano; 5 each R27 is independently CrC6 alkyl; CrC6 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, CrC4 alkyl, C1-C4 haloalkyl, Cj-C4 alkoxy, C]-C4 haloalkoxy, nitro or cyano; and n is 0, 1 or 2; provided that (a) when E is 1,2-phenylene optionally substituted with one of R3,R4 or both R3 and R4; R3 is H; R4 is H; R2 is CH3; W is O; G is C; A is 0 with the floating double bond is attached to G; X is 0CH3; Y is O, CH20 or CH2ON = C(CH3); then Z is other than 6-CF3-2-pyrazinyl; and (b) when E is 1,2-phenylene optionally substituted with one of R3,R4 or both R3 and R4; R3 is H; R4 is H; R2 is CH3; W is 0; G is N; A is N with the floating double bond is attached to A; X is 0CH3, Y is CH2ON = C(CH3) or CH2S; then Z is other than 6-CF3-2-pyrazinyl. 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: IB INTfciicwu/U PROPERTY OFFIC OF N.Z. 2 2 FEB 1999 RECEIVED * 11 a- 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 INTELLECTUAL PROPERTY OFFICE OF N.Z. 2 2 FEB 1999 RECEIVED WO 97/00612 PCT/US96/10326 12 C(=0) 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; 5 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(CrC6 alkyl); or NO(C,-C6 alkyl); 10 X is H; OR1; S(0)mR1; halogen; CrCg alkyl; Cj-Cg haloalkyl; C3-Cg cycloalkyl; cyano; NH2; NHR'; N(CpCg alky^R1; NH(CrCg alkoxy); or N(CpCg alkoxy)R1; R1 is CpCg alkyl; CpCg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 15 alkoxycarbonyl; R2 is H; CpCg alkyl; Cj-Cg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; hydroxy; C]-C2 alkoxy; or acetyloxy; R3 and R4 are each independently halogen; cyano; nitro; hydroxy; CrC6 alkyl; 20 Cj-Cg haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; Cj-C6 alkoxy; CpCg haloalkoxy; C2-Cg alkenyloxy; C2-Cg alkynyloxy; CpCg alkylthio; Cj-Cg alkylsulfinyl; Cj-Cg alkylsulfonyl; formyl; C2-Cg alkylcarbonyl; C2-Cg alkoxycarbonyl; NH2C(0); (CrC4 alkyl)NHC(O); (CrC4 alkyl)2NC(0); Si(R25)3; Ge(R25)3; 25 (R25)3Si-0=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 30 CpC3 alkyl; R5 is H; CpCg alkyl; Cj-Cg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; Y is -0-; -S(0)n-; -NR15-; -C(=0)-; -CH(OR15)-; -CHR6-; -CHR6CHR6-; 35 -CR6=CR6-; -C=C-; -CHR150-; -OCHR15-; -CHR15S(0)n-; -S(0)nCHR15-; -CHR150-N=C(R7)-; -(R7)C=N-OCH(R15)-; -C(R7)=N-0-; -0-N=C(R7)-; WO 97/00612 13 PCT/US96/10326 -CHR15OC(=0)N(R.15)-; -CHR15OC(=S)N(R15)-; -CHR150C(=0)0-; -CHR150C(=S)0-; -CHR0C(=0)S-; -CHR15OC(=S)S-; -CHR15SC(=0)N{R1-s)-; -CHR15SC(=S)N(R15)-; -CHR 15SC(=0)0-; -CHR15SC(=S)0-; -CHR15SC(=0)S-; -CHR15SC(=S)S-; 5 -CHRI5SC(=NR15)S-; -CHR15N(R'5)C(=0)N(R15)-; -CHR150-N(Rl5)C(=0)N(R'5)-; -CHR150-N(R15)C(=S)N(R15)-; -CHR150-N=C(R7)NR15-; -CHRi50-N=C(R7)0CH2-; -CHR150-N=C(R7)-N=N-; -CHRi50-N=C(R7)-C(=0)-; -CHR150-N=C(R7)-C(=N-A2-Z1 )-A* -; 10 -CHR150-N=C(R7)-C(R7)=N-A2-A3-; -CHR150-N=C(-C(R7)=N-A2-Z1)-; -CHR 150-N=C(R7)-CH20-; -CHR150-N=C(R7)-CH2S-; -0-CH2CH20-N=C(R7)-; -CHR150-C(R15)=C(R7)-;-CHR150-C(R7)=N-; -CHR15S-C(R7)=N-; -C(R7)=N-NR15-; -CH=N-N=C(R7)-; -CHR15N(R15)-N=C(R7)-;-CHR^N(COCH3)-N=C(R7)-; 15 -0C(=S)NR15C(=0)-; -CHR6-C(=W1)-A1-; -CHR6CHR6-C(=W1)-A1-; -CR6=CR6-C(=Wl)-A1-; -C=C-C(=W1 )-A1 -; -N^R^C^W^-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; 20 Z1 is H or -A3-Z; W1 is O or S; A1 is O; S; NR15; or a direct bond; A2 is O; NR15; or a direct bond; A3 is -C(=0)-; -S(0)2-; or a direct bond; 25 each R6 is independently H; 1-2 CH3; C2-C3 alkyl; Cj-C3 alkoxy; C3-Cg cycloalkyl; formylamino; C2-C4 alkylcarbonylamino; C2-C4 alkoxycarbonylamino; NH2C(0)NH; (CrC3 alkyl)NHC(0)NH; (Cj-C3 alkyl)2NC(0)NH; N(C]-C3 alkyl)2; piperidinyl; morpholinyl; 1-2 halogen; cyano; or nitro; 30 each R7 is independently H; CpC6 alkyl; Cj-Cg haloalkyl; CrCg alkoxy; CrCg haloalkoxy; Cj-Cg alkylthio; CpC6 alkylsulfinyl; C]-C6 alkylsulfonyl; Cj-Cg haloalkylthio; Cj-Cg haloalkylsulfinyl; C]-Cg haloalkylsulfonyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; halogen; cyano; 35 nitre; hydroxy; amino; NH(CrC6 alkyl); N(Cj-Cg alkyl)2; or morpholinyl; WO 97/00612 PCT/US96/10326 14 each Z is independently selected from: i) C]-C]o alkyl, C^-Ciq alkenyl, or C^-Cjq alkynyl each substituted with R9 and optionally substituted with one or more R1(); ii) C3-C8 cycloalkyl, C3-Cg cycloalkenvl or phenyl each substituted with R9 5 and optionally substituted with one or more R1C); 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 10 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; 15 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(=0) 20 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; 25 each Q is independently selected from the group -CHR13-, -NR13-, -0-, and -S(0)p-; R8 is H; 1-2 halogen; CpCg alkyl; CrCg haloalkyl; CrC6 alkoxy; CpC6 haloalkoxy; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; CrC6 alkylthio; CpCg haloalkylthio; C]-C6 alkylsulfinyl; CrC6 alkylsulfonyl; 30 C3-Cg cycloalkyl; C3-C6 alkenyloxy; CC^Cj-Cg alkyl); NH(CrC6 alkyl); NCCpCg alkyOo; cyano; nitro; SiR19R20R21; or GeR19R20R21; R9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each substituted with R11 and optionally substituted with R12; 3." each R10 is independently halogen; CrC4 alkyl; C1-C4 haloalkyl; CrC4 alkoxy; nitro; or cyano; or WO 97/00612 PCT/US96/10326 when R9 and an R10 are attached to adjacent atoms on Z, R9 and said adjacently attached R1® can be taken together as -OCHiO- or -0CH2CH20-; each CH2 group of said taken together R9 and R10 optionally substituted with 1-2 halogen; or 5 when Y and an R10 are attached to adjacent atoms on Z and Y is -CHR150-N=C(R7)-, -0-N=C(R7)-, -0-CH2CH20-N=C(R7)-, -CHR150-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; 10 J is -CHr; -CH2CHr; -OCHr; -CHoO-; -SCHr; -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-Cg haloalkynyl; C2-C6 alkoxyalkyl; C2-C6 alkylthioalkyl; Cj-Cg alkoxyalkynyl; C7-C]o 15 tetrahydropyranyloxy alkynyl; benzyloxy methyl; C3-C6 alkenyloxy; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy; C3-C6 haloalkynyloxy; C2-C6 alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; Cj-C4 alkylthio; C]-C4 haloalkylthio; Cj-C4 alkylsulfinyl; C]-C4 haloalkylsulfinyl; Cj-C4 alkylsulfonyl; C]-C4 haloalkylsulfonyl; C3-C6 alkenylthio; C3-C6 20 haloalkenylthio; C2-C6 alkylthioalkylthio; thiocyanato; hydroxy; N(R26)2; SF5; (R25)3Si-C=C-; OSi(R25)3; OGe(R25)3; C(=0)R26; C(=S)R2&; C(=0)0R26; C(=S)OR26; C(=0)SR26; C(=S)SR26; C(=0)N(R26)2; C(=S)N(R26)2; 0C(=0)R26; OC(=S)R26; SC(=0)R26; SC(=S)R26; N(R26)C(=0)R26; N(R26)C(=S)R26; 0C(=0)0R27; 0C(=0)SR27; 25 0C(=0)N(R26)2; SC(=0)0R27; SC(=0)SR27; S(0)20R26; S(0)2N(R26)2; OS(G)2R27; N(R26)S(0)2R27; or phenyl, phenoxy, benzyl, benzyloxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted with halogen, Cj-C4 alkyl, Cj-C4 haloalkyl, Cj-C4 alkoxy, Cj-C4 haloalkoxy, nitro or cyano; 30 R12 is 1-2 halogen; Cj-C4 alkyl; C]-C4 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C2-C6 alkoxyalkyl; C2-C6 alkylthioalkyl; C3-C6 alkoxyalkynyl; C7-Cjo tetrahydropyranyloxyalkynyl; benzyloxymethyl; CpC4 alkoxy; Cj-C4 haloalkoxy; C3-C6 alkenyloxy; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy; C3-Cg haloalkynyloxy; C2-C6 35 alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; CrC4 alkylthio; C]-C4 haloalkylthio; C|-C4 alkylsulfinyl; CrC4 haloalkylsulfinyl; PCT/TJS96/10326 C1-C4 alkylsulfonyl; C|-C4 haloalkylsulfonyl; C3-Cg alkenylthio; C^-Cg 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(=0)R26; C(=S)R26; C(=0)0R26; C(=S)OR26; C(=0)SR26: C(=S)SR26; C(=0)N(R26)2; C(=S)N(R26)2; 0C(=0)R26; OC(=S)R26; SC(=0)R26; SC(=S)R26; N(R26)C(=0)R26; N(R26)C(=S)R26; 0C(=0)0R27; 0C(=0)SR27; 0C(=0)N(R26)2; SC(=0)0R27; SC(=0)SR27; S(O)20R26; S(0)2N(R26)2; 0S(0)2R27; N(R26)S(0)2R27; or phenyl, phenoxy, benzyl, benzyloxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted with halogen, CrC4 alkyl, CrC4 haloalkyl, CrC4 alkoxy, CrC4 haloalkoxy, nitro or cyano; each R13 is independently H; Cj-Cg alkyl; Cj-Cg haloalkyl; or phenyl optionally substituted with halogen, CrC4 alkyl, C1-C4 haloalkyl, Cj-C4 alkoxy, Cj-C4 haloalkoxy, nitro or cyano; R14 is H; halogen; C]-C6 alkyl; Cj-Cg haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; C2-Cg haloalkynyl; or C3*C6 cycloalkyl; each R15 is independently H; C1-C3 alkyl; C3-Cg cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, Cj-C4 alkyl, Cj-C4 haloalkyl, Cj-C4 alkoxy, C]-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 -CHR150-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(Cj-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; C^-Cq cycloalkyl; or phenyl optionally substituted with halogen, Ci~C4 alkyl, Cj-C4 haloalkyl, Cj-C4 alkoxy, CpC4 haloalkoxy, nitro or cyano; r!9, r20t r21 each independently C]-C6 alkyl; C2-C6 alkenyl; CrC4 alkoxy; or phenyl; each R25 is independently C]-C4 alkyl; CrC4 haloalkyl; C2-C4 alkenyl; CpC4 alkoxy; or phenyl; each R26 is independently H; Cj-Cg alkyl; Cj-Cg haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; or phenyl WO 97/00612 PCT/US96/10326 17 or benzyl, each optionally substituted on the phenyl ring with halogen, Cj-C4 alkyl, C]-C4 haloalkyl, C]-C4 alkoxy, Cj-C4 haloalkoxy, nitro or cyano; each R27 is independently Cj-Cg alkyl; Cj-Cg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; or phenyl 5 or benzyl, each optionally substituted on the phenyl ring with halogen, CrC4 alkyl, CrC4 haloalkyl, CrC4 alkoxy, CrC4 haloalkoxy, nitro or cyano; m, n and p are each independently 0, 1 or 2; r is 0 or 1; and s is 2 or 3. 10 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: rOH A —N R2 n 15 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 CR^4; 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 20 floating double bond is attached to A; W is O; S; NH; N(CrCg alkyl); or NO(CrC6 alkyl); X is OR1; S(0)mR1; or halogen; R1 is Cj-Cg alkyl; C]-Cg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 25 alkoxycarbonyl; R2 is H; Cj-Cg alkyl; Cj-Cg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; hydroxy; Cj-C2 alkoxy; or acetyloxy; R3 and R4 are each independently halogen; cyano; nitro; hydroxy; Cj-Cg alkyl; 30 Cj-Cg haloalkyl; C2-Cg alkenyl; C2-C6 haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; Cj-Cg alkoxy; Cj-Cg haloalkoxy; C2-C6 alkenyloxy; C2-C6 WO 97/00612 PCT/US96/10326 18 alkynyloxy; Cj-Cg alkylthio; CpCg alkylsulfinyl; CrCg alkylsulfonyl; formyl; C2-C6 alkylcarbonyl; C2-Cg alkoxycarbonyl; NH2C(0); (CrC4 alkyl)NHC(O); (C,-C4 alkyl)2NC(0); Si(R25)3; Ge(R25)3; (R~^)3Si-C=C or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each 5 substituted with R8 and optionally substituted with one or more R10; or when R3 and R4 are attached to adjacent atoms, R3 and R4 can be taken together as C3-C5 alkylene, C3-C5 haloalkylene, G3-C5 alkenylene or C3-C5 haloalkenylene each optionally substituted with 1-2 Cj-C3 alkyl; R5 is H; Cj-Cg alkyl; Cj-C6 haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-C6 10 alkynyl; C2-C6 haloalkynyl; C3-Cg cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; R8 is H; 1-2 halogen; Cj-Cg alkyl; Cj-Cg haloalkyl; Cj-Cg alkoxy; Cj-Cg haloalkoxy; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; Cj-Cg alkylthio; Cj-Cg haloalkylthio; Cj-Cg alkylsulfinyl; Cj-Cg alkylsulfonyl; 15 C3-C6 cycloalkyl; C3-Cg alkenyloxy; C02(Cj-Cg alkyl); NH(Cj-Cg alkyl); N(Cj-Cg alkyl)2; cyano; nitro; SiR19R20R21; or GeR19R20R21; each R10 is independently halogen; CrC4 alkyl; Cj-C4 haloalkyl; C]-C4 alkoxy; nitro; or cyano; R14 is H; halogen; Cj-Cg alkyl; Cj-Cg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; 20 C2-Cg alkynyl; C2-Cg haloalkynyl; or C3-Cg cycloalkyl; R19, R20 and R21 are each independently Cj-Cg alkyl; C2-C6 alkenyl; Cj-C4 alkoxy; or phenyl; each R25 is independently Cj-C4 alkyl; Cj-C4 haloalkyl; C2-C4 alkenyl; Cj-C4 alkoxy; or phenyl; and 25 m is 0, 1 or 2. 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, /-propyl, or the different butyl, pentyl or hexyl isomers. The 30 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 35 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 WO 97/00612 PCT/US96/10326 19 comprised of multiple triple bonds such as 2,5-hexadivnyl. "Alkvlene" denotes a straight-chain alkanediyl. Examples of "alkylene" include CI-^CHtCHt, CH2CH2CH2CH2, CH2CH2CH2CH2CH2. "Alkenylene" denotes a straight-chain alkenedivl containing one olefinic bond. Examples of "alkenylene" include CH2CH=CH, 5 CH2CH2CH=CH, CH2CH=CHCH2 and CH2CH=CHCH2CH2. "Alkoxy" includes, for example, methoxy, ethoxy, rc-propyloxy, isopropyloxy and the different butoxy, pernoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. "Alkoxyalkoxy" denotes alkoxy 10 substitution on alkoxy. "Alkenyloxy" includes straight-chain or branched alkenyloxy moieties. Examples of "alkenyloxy" include P^C^HCHoO, (CH3)2C=CHCH->0, (CH3)CH=CHCH20, (CH3)CH=C(CH3)CH20 and CH2=CHCH2CH20. "Alkynyloxy" includes straight-chain or branched alkynyloxy moieties. Examples of "alkynyloxy" include HOCCH2O, CH3GsCCH20 and CH-^CsCCHbCI-^O. "Alkylthio" includes 15 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 CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. "Alkylthioalkylthio" denotes alkylthio substitution on alkylthio. Analogously, 20 "alkylthioalkoxy" denotes alkylthio substitution on alkoxy. "Alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH3S(0). CH3CH2S(0), CH3CH2CH2S(0), (CH3)2CHS(0) and the different butylsulfmyl, pentylsulfinyl and hexylsulfmyl isomers. Examples of "alkylsulfonyl" include CH3S(0)2, CH3CH2S(0)2, CH3CH2CH2S(0)2, (CH3)2CHS(0)2 and the different butylsulfonyl, 25 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 30 on alkoxy. Examples of "trialkylsilylalkoxyalkoxy" includes, for example, (CH3)3SiCH2CH20CH20. 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 Hiickel rule is satisfied). The term "nonaromatic carbocyclic ring system" denotes fully saturated carbocycles as well as 35 partially or fully unsaturated carbocycles where the Hiickel rule is not satisfied by any of the rings in the ring system. The term "aromatic heterocyclic ring system" includes fully WO 97/00612 PCT/US96/10326 20 aromatic heterocycles and heterocycles in which at least one ring of a poiycyclic ring system is aromatic (where aromatic indicates that the Hiickel rule is satisfied 1. The term "nonaromatic heterocyclic ring system" denotes fully saturated heterocycles as well as panially or fully unsaturated heterocycles where the Hiickel rule is not satisfied by any of 5 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 jV-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 10 can form TV-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 15 alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F3C, C1CH2, CF3CH2 and CF3CC12. 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, 20 CC13C^C and FCH2C^CCH2. Examples of "haloalkoxy" include CF30, CC13CH20, HCF2CH2CH2O and CF3CH20. Examples of "haloalkylthio" include CC13S, CF3S, CC13CH2S and C1CH2CH2CH2S. Examples of "haloalkylsulfinyl" include CF3S(0), CC13S(0), CF3CH2S(0) and CF3CF2S(0). Examples of "haloalkylsulfonyl" include CF3S(0)2, CC13S(0)2, CF3CH2S(0)2 and CF3CF2S(0)2. 25 The total number of carbon atoms in a substituent group is indicated by the "Cj-Cj" prefix where i and j are numbers from 1 to 10. For example, CrC3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl. Examples of "alkylcarbonyl" include C(0)CH3, C(0)CH2CH2CH3 and C(0)CH(CH3)2. Examples of "alkoxycarbonyl" include CH30C(=0), CH3CH20C(=0), CH3CH2CH20C(=0), (CH3)2CH0C(=0) and 30 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 35 R13, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. WO 97/00612 PCT/US96/10326 21 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 stereoisomers) or when 5 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, /V-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. 10 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, ammonia, or triethylamine) 15 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 20 above, and 7V-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; 1//-pyrrole-1,2-, 2,3- and 3.4-diyl; 2,3- and 3,4-furandiyl; 2,3- and 3,4-thiophenediyl; l//-pyrazole-l,5-, 3,4- and 4,5-diyl; l//-imidazole-l,2-, 4,5- and 25 1,5-diyl; 3,4- and 4,5-isoxazolediyl; 4,5-oxazolediyl; 3,4- and 4.5-isothiazolediyl;4,5-thiazolediyl; l//-l,2,3-triazole-l,5- and 4.5-diyl; 2//-l,2,3-triazole-4,5-diyl; 1//-1,2,4-triazole-1,5-diyl; AH-1,2,4-triazole-3,4-diyl; 1,2,3-oxadiazole-4,5-diyl; l,2,5-oxadiazole-3,4-diyl; l,2,3-thiadiazole-4,5-diyl; 30 l,2,5-thiadiazole-3,4-diyl; l//-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; l,2,4-triazine-5,6-diyl; 1//-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-, 35 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-, WO 97/00612 5 10 15 20 25 30 PCT/US96/10326 4.5-, 5,6- and 6,7-diyI; l/f-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; ltf-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; l,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; l,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,l-&]thiazole-2,6-, 2,7-, 3,6-, 3,7-, 2,3- and 6,7-diyl; thiazolo[2,3-c]-l,2,4-triazole-2,5-, 2,6-, 5,6-diyl; 2-oxo-l,3-benzodioxole-4,5- and 5,6-diyl; 1.3-dioxo-l/f-isoindole-2,4-, 2,5-, 4,5- and 5,6-diyl; 2-oxo-2tf-l-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; [l,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-2//-l,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-<f]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-l,l,3-trioxo-l,2-benzisothiazole-2,4-, 2,5-, 2,6-, 2,7-, 4.5-, 5,6- and 6,7-diyl; l,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-4//-cyclohepta[£>]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 WO 97/00612 PCT/US96/10326 23 ring system optionally substituted with one of R-\ R4. or both R3 and R4; W is O; R1 is Cj-Cj alkyl or Cj-Ct haloalkyl; 5 R~ is H; CpC^ alkyl; Cj-Cg haloalkyl; or Cj-Cg cycloalkyl; R3 and R4 are each independently halogen; cyano; nitro; Cj-C6 alkyl; Cj-C6 haloalkyl; Cj-C6 alkoxy; C]-C6 haloalkoxy; Cj-C6 alkylthio; CpCg alkylsulfonyl; C2-C^ alkylcarbonyl; C2-C5 alkoxycarbonyl; (C,-C4 alkyl)NHC(O); (Cj-C4 alkyl)2NC(0); benzoyl; or 10 phenylsulfonyl; Y is -0-; -S(0)n~; -NR15-; -C(=0)-; -CH(OR15)-; -CH2-; -CH2CH2-; -CH=CH-; -C=C-; -CH20-; -OCH2-; -CH2S(0)n-; -S(0)nCH2-; -CH20-N=C(R7)-; -(R7)C=N-OCH(R15)-; -C(R7)=N-0-; or a direct bond; 15 R7 is H; CpCg alkyl; Cj-Cg haloalkyl; Cj-C6 alkoxy; Cj-Cg alkylthio; C2-C6 alkenyl; C2-Cg alkynyl; C3-C6 cycloalkyl; halogen; or cyano; or when Y and an R10 are attached to adjacent atoms on Z and Y is -CH20-N=C(R7)-, R7 and said adjacently attached R10 can be taken 20 together as -(CH2VJ- such that J is attached to Z; Z is selected from the group Cj-Cjg alkyl; C3-Cg cycloalkyl; phenyl; naphthalenyl; anthracenyl; phenanthrenyl; l//-pyrrolyl; furanyl; thienyl; l//-pyrazolyl; l//-imidazolyl; isoxazolyl; oxazolyl; isoihiazolyl; thiazolyl; l/f-l,2,3-triazolyl; 2/f-l,2,3-triazolyl; 25 l//-l,2,4-triazolyl; 4//-l,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/f-tetrazolyl; 2//-tetrazolyl; pyridinyl; pyridazinyl; pyrimidinyl; pyrazinyl; 1,3,5-triazinyl; 1,2,4-triazinyl; 30 1,2,4,5-tetrazinyl; l//-indolyl; benzofuranyl; benzo[£>]thiophenyl; l//-indazolyl; l//-benzimidazoiyl; benzoxazolyl; benzothiazolyl; quinolinyl; isoquinolinyl; cinnolinyl; phthalazinyl; quinazolinyl; quinoxalinyl; 1,8-naphthyridinyl; pteridinyl; 2,3-dihydro-l//-indenyl; 1,2,3,4-teirahydronaphthalenyl; 35 6,7,8,9-tetrahydro-5/f-benzocycloheptenyl; 5,6,7,8,9,10-hexahydrobenzocyclooctenyl; WO 97/00612 PCT/US96/10326 24 2.3-dihydro-3-oxobenzofuranyl; 1,3-dihydro-1 -oxoisobenzofuranyl; 2.3-dihydro-2-oxobenzofuranyl; 3.4-dihydro-4-oxo-2//- 1-benzopyranyl; 3.4-dihydro-1 -oxo- l/f-2-benzopyranyl; 5 3,4-dihydro-3-oxo-l//-2-benzopyranyl; 3,4-dihydro-2-oxo-2//- 1-benzopyranyl; 4-oxo-4//- 1-benzopyranyl; 2-oxo-2H- 1-benzopyranyl; 2,3,4,5-tetrahydro-5-oxo- 1-benzoxepinyl; 2,3,4,5-tetrahydro-2-oxo-l-benzoxepinyl; 10 2,3-dihydro-1,3-dioxo-1 tf-isoindoly 1; 1,2,3,4-tetrahy dro-1,3-dioxoisoquinolinyl; 3,4-dihydro-2,4-dioxo-2//-l,3-benzoxazinyl; 2-oxo-1,3-benzodioxyl; 2.3-dihydro-l,l,3-trioxo-l,2-benzisothiazolyl; 9//-fluorenyl; 15 azulenyl; and thiazolo[2,3-c]-l,2,4-triazolvl; each group substituted with R9 and optionally substituted with one or more R10; and R15 is H; CrC3 alkyl; or C3-C5 cycloalkyl. Preferred 2. Methods of Preferred 1 wherein: E is selected from the group 1,2-phenylene; 1,6-, 1,7-, 1,2-, and 20 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[£>]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, 25 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; 30 R7 is H; CpC6 alkyl; CpCg haloalkyl; CpCg alkoxy; Cj-Cg alkylthio; C2"Cg alkenyl; C2-C6 alkynyl; cyclopropyl; halogen; or cyano; or when Y and an R10 are attached to adjacent atoms on Z and Y is -CH20-N=C(R7)-, R7 and said adjacently attached R10 can be taken together as -(CUbVJ- such that J is attached to Z; 35 J is -CH2- or -CH2CH2-; and r is 1. WO 97/00612 PCT/US96/I0326 25 Preferred 3. Methods of Preferred 2 wherein: E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; A is O or N; 5 X is OR1; R1 is C1-C3 alkyl; R2 is H or Cj-C2 alkyl; Y is -0-; -S(0)n-; -NR15-; -C(=0)-; -CH(OR15)-; -CH2-; -CH2CH2-; -CH=CH-; -C=C-; -CH20-; -OCH2-; -CH2S(0)n-; -S(0)nCH2-; or 10 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; CJ-C3 alkyl; or cyclopropyl. 15 Preferred 4. Methods of Preferred 3 wherein: R1 is methyl; R2 is methyl; Y is -0-; -S(0)n-; -NR15-; -C(=0)-; -CH(OR15)-; -CH2-; or a direct bond;and 20 R9 is H; halogen; Cj-Cg alkyl; Cj-Cg haloalkyl; Cj-Cg alkoxy; Cj-Cg haloalkoxy; C]-C6 alkylthio; Cj-Cg haloalkylthio; Cj-Cg alkylsulfinyl; Cj-Cg alkylsulfonyl; C3-Cg cycloalkyl; C02(Cj-C6 alkyl); -C(R18)=NOR17; cyano; nitro; SF5; SiR22R23R24; or GeR22R23R24; or R9 is phenyl, benzyl, phenoxy, 25 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 30 substituted with R10; and Y is -O-; and R9 is phenyl optionally substituted with one of R11, R12, or both R11 and R12 WO 97/00612 PCT/US96/10326 26 Most preferred arc methods of Preferred 5 where the compound is selected from the group: 4-[2-[[3-[3,5-bis(trifluoromethyl)phenvl]-l,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4-dihydro-5-methoxy-2-methyl-3//-1,2,4-triazol-3-one; and 5 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]oxy]-6- methylphenyl]-2,4-dihydro-5-methoxy-2-methyl-3//-l,2,4-triazol-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 W-oxides and agriculturally 10 suitable salts thereof, wherein: R1 is methyl; R2 is methyl; Y is -0-; -S(0)n-; -NR15-; -C(=0)-; -CH(OR15)-; -CH2-; or a direct bond; and 15 R9 is H; halogen; Cj-Cg alkyl; Cj-Cg haloalkyl; Cj-Cg alkoxy; C]-C6 haloalkoxy; CrC6 alkylthio; CrC6 haloalkylthio; CrC6 alkylsulfinyl; CpCg alkylsulfonyl; C3-C6 cycloalkyl; C02(CrC6 alkyl); -C(R18)=NOR17; cyano; nitro; SF5; SiR22R23R24; or GeR22R23R24; or R9 is phenyl, benzyl, phenoxy, 20 pyridinyl, thienyl, furanyl, or pyrimidinyl each optionally substituted with one of R11, R12, or both R11 and R12. Preferred 2A. Compounds of Preferred IA wherein: Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; 1,2,4-thiadiazolyl; and pyrazinyl; each group substituted with R9 25 and optionally substituted with R10; and Y is -0-; and R9 is phenyl optionally substituted with one of R11, R12, or both R11 and R12. Most preferred are compounds of Preferred IA selected from the group: 30 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-l,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4- dihydro-5-methoxy-2-methyl-3//-l,2,4-triazol-3-one; 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-l,2,4-thiadiazol-5-yl]oxy]-6-methylphenyl]-2,4-dihydro-5-methoxy-2-methyl-3//-l,2,4-triazol-3-one; 4-[2-[[3-( 1,1-dimethylethyl)-1,2,4-thiadiazol-5-yl]oxy]-6-methylpheny]]-2,4-35 dihydro-5-methoxy-2-methyl-3//-l,2,4-triazol-3-one; WO 97/00612 PCT/US96/10326 27 4-[2-[[3-( l,l-dimethylethyl)-l,2,4-thiadiazol-5-yl]oxv]phenyl]-2,4-dihydro-5-methoxy-2-niethyl-3£M,2,4-triazol-3-one; 4-[2-[[3-(3,4-dichlorophenyl)-l,2,4-thiadiazol-5-yl]oxy]phen\i]-2,4-dihydro-5-methoxy-2-methyl-3W-1,2.4-triazol-3-one; 5 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[3-[3-(trifluoromethoxy)phenyl]-1,2,4- thiadiazol-5-yl]oxy]phenyl]-3//-1,2,4-triazol-3-one; 4-[2-[[3-(4-bromophenyl)-l,2,4-thiadiazol-5-vl]oxy]phenyl]-2,4-dihydro-5-methoxy-2-methyl-3//-l,2,4-triazol-3-one; 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[5-methyl-4-[3-(trifluoromethyl)phenyl]-10 2-thiazolyl]oxy]phenyl]-3/f-l,2,4-triazol-3-one; and 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[6-[4-(trifluoromethyl)phenyl]-2-pvrazinyl]oxy]phenyl]-3//-l,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 15 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 ol the compounds of Formula IA 20 and the compositions described herein. The preferred methods of use are those involving the above preferred compounds of Formula LA. 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 25 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 30 Formula IA. Preferred compounds of Formula EB for reasons of better fungicidal or arthropodicidal activity and/or ease of synthesis are: Preferred IB. Compounds of Formula IB above, and /V-oxides and agriculturally suitable salts thereof, wherein: 35 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; l//-pyrrole-l,2-, 2.3- and WO 97/00612 PCT/US96/10326 2S 3.4-diyl; 2,3- and 3,4-furandiyl; 2,3- and 3,4-thiophenediyl; l//-pyrazole-l,5-, 3,4- and 4,5-diyl; 1//-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; l//-l,2,3-triazole-l,5- and 5 4,5-diyl; 2H-1,2,3-triazole-4,5-diyl; 1H-1,2,4-triazole-1,5-diyl; AH-1,2,4-triazole-3,4-diyl; 1,2,3-oxadiazole-4,5-diyl; l,2,5-oxadiazole-3,4-diyl; l,2,3-thiadiazole-4,5-diyl; l,2,5-thiadiazole-3,4-diyl; l//-tetrazole-1,5-diyl; 2,3- and 3,4-pyridinediyl; 3,4- and 4,5-pyridazinediyl; 4,5-pyrimidinediyl; 10 2,3-pyrazinediyl; l,2,3-triazine-4,5-diyl; l,2,4-triazine-5,6-diyl; 1 //-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[fc]thiophene-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-, 15 4,5-, 5,6- and 6,7-diyl; l//-indazole-l,4-, 1,5-, 1,6-, 1,7-, 3,4-, 3,5-, 3.6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; li/-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; 20 l,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 25 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; l,8,-naphthyridine-2,5-, 2,6-, 2,7-, 3,5-, 30 3,6-, 4,5-, 2,3- and 3,4-diyl; 2,6-, 2,7-, 4,6-, 4,7-, 6,7-pteridinediyl; pyrazolo[5,l-£]thiazole-2,6-, 2,7-, 3,6-, 3,7-, 2,3- and 6,7-diyl; thiazolo[2,3-c]-l,2,4-triazole-2,5-, 2,6-, 5,6-diyl; 2-oxo-l,3-benzodioxole-4,5- and 5,6-diyl; 1.3-dioxo-l//-isoindole-2,4-, 2,5-, 4,5- and 5,6-diyl; 35 2-oxo-2/Z-l-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; [l,2,4]triazolo[l,5-a]pyridine-2,5-, 2.6-, WO 97/00612 PCI7US96/10326 29 2,7-, 2,8-, 5,6-, 6,7- and 7,8-diyl; 3.4-dihydro-2,4-dioxo-2//-l,3-benzoxazine-3,5-, 3,6-. 3,7-, 3,8-, 5.6-, 6,7- and 7,8-diyl; 2,3-dihvdro-2-oxo-3,4-, 3.5-, 3,6-, 3,7-, 4.5-, 5,6- and 6,7-benzofurandiyl; thieno[3,2-J]thiazole-2.5-, 2,6-, 5 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-l,l,3-trioxo-l,2-benzisothiazole-2,4-, 2,5-, 2,6-, 2,7-, 4.5-, 5,6- and 6,7-diyl; l,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-, 10 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-4//-cyclohepta[£]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 15 and R4; Wis O; R1 is CJ-C3 alkyl or C1-C3 haloalkyl; R2 is H; Cj-Cg alkyl; C]-Cg haloalkyl; or cycloalkyl; R3 and R4 are each independently halogen; cyano; nitro; Cj-Cg alkyl; 20 Cj-Cg haloalkyl; Cj-Cg alkoxy; Cj-Cg haloalkoxy; Cj-Cg alkylthio; Cj-C6 alkylsulfonyl; C2-Cg alkylcarbonyl; C2-Cg alkoxycarbonyl; (Cj-C4 alkyl)NHC(O); (Cj-C4 alkyl)2NC(0); benzoyl; or phenylsulfonyl; Y is -O-; -S(0)n-; -NR15-; -C(=0)-; -CH(OR15)-; -CH2-; -CH2CH2-; 25 -CH=CH-; -C=C-; -CH20-; -OCH2-; -CH2S(0)n-; -S(0)nCH2-; -CH20-N=C(R7)-; -(R7)C=N-OCH(R15)-; -C(R7)=N-0-; or a direct bond; R7 is H; Cj-Cg alkyl; Cj-Cg haloalkyl; Cj-Cg alkoxy; Cj-Cg alkylthio; C2-Cg alkenyl; C2-Cg alkynyl; C3-Cg cycloalkyl; halogen; or cyano; 30 or when Y and an R10 are attached to adjacent atoms on Z and Y is -CH20-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 Cj-Cjo alkyl; C3-C8 cycloalkyl; phenyl; 35 naphthalenyl; anthracenyl; phenanthrenyl; l//-pyrrolyl; furanyl; thienyl; l//-pyrazolyl; l//-imidazolyl; isoxazolyl; oxazolyl; • wo 97/00612 pct/us96/10326 30 isothiazolyl; thiazolyl; \H- 1,2.3-triazolyl; 2//-l,2,3-triazolyl; 1H-1,2,4-triazolyl; AH-1,2,4-triazolyl; 1,2,3-oxadiazolyl; 1,2,4-oxadiazolyl; 1,2.5-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,3-lhiadiazolyl; 1,2,4-thiadiazolyl; 1.2,5-thiadiazolyl; 5 1,3,4-thiadiazolyl; 1 //-tetrazolyl; 2//-tetrazolyl; pyridinyl; pyridazinyl; pyrimidinyl; pyrazinyl; 1,3,5-triazinyl; 1,2,4-triazinyl; 1,2,4,5-tetrazinyl; l//-indolyl; benzofuranyl; benzo[£>]thiophenyl; l//-indazolyl; l//-benzimidazolyl; benzoxazolyl; benzothiazolyl; quinolinyl; isoquinolinyl; cinnolinyl; phthalazinyl; quinazolinyl; 10 quinoxalinyl; 1,8-naphthyridinyl; pteridinyl; 2,3-dihydro-ltf-indenyl; 1.2.3.4-tetrahydronaphthalenyl; 6,7,8,9-tetrahydro-5//-benzocycloheptenyl; 5,6,7,8,9,10-hexahydrobenzocyclooctenyl; 2.3-dihydro-3-oxobenzofuranyl; 1,3-dihydro- 1-oxoisobenzofuranyl; 15 2,3-dihydro-2-oxobenzofuranyl; 3.4-dihydro-4-oxo-2//-1 -benzopyranyl; 3,4-dihydro-1 -oxo-1 //-2-benzopyranyl; 3,4-dihydro-3-oxo-l//-2-benzopyranyl; 3,4-dihydro-2-oxo-2//-1 -benzopyranyl; A-oxo-AH-1 -benzopyranyl; 20 2-0X0-2//-1-benzopyranyl; 2.3.4.5-tetrahydro-5-oxo-1 -benzoxepinyl; 2,3,4,5-tetrahydro-2-oxo-l-benzoxepinyl; 2,3-dihydro-1,3-dioxo- l//-isoindolyl; l,2,3,4-tetrahydro-l,3-dioxoisoquinolinyl; 25 3,4-dihydro-2,4-dioxo-2//- 1,3-benzoxazinyl; 2-oxo-1,3-benzodioxyl; 2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazolyl; 9//-fluorenyl; azulenyl; and thiazolo[2,3-c]-l,2,4-triazolyl; each group substituted with R9 and optionally substituted with one or more R10; and 30 R15 is H; Cj-C3 alkyl; or C3-C6 cycloalkyl. Preferred 2B. Compounds of Preferred IB 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; 35 2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl; and benzo[6]thiophene-2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-diyl; WO 97/00612 PCT/US96/10326 31 each aromatic ring system optionally substituted with one of R3, R4, or both R3 and R4; Z is selected from the group phenyl; naphthaJenyl; 2-thiazolyl; 1,2,4-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,4-thiadiazolyl; 5 1,3,4-thiadiazolyl; pyridinyl; and pyrimidinyl; each group substituted with R9 and optionally substituted with one or more R10; R7 is H; Cj-Cg alkyl; Cj-Cg haloalkyl; Cj-C6 alkoxy; CrCg alkylthio; C2-C6 alkenyl; C^-Cg alkynyl; cyclopropyl; halogen; or cyano; or when Y and an R1® are attached to adjacent atoms on Z and Y is 10 -CH20-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 -CHo- or -CH2CH2-; and r is 1. Preferred 3B. Compounds of Preferred 2B wherein: 15 E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; A is O or N; X is OR1; R1 is CrC3 alkyl; 20 R2isHorCrC2alkyl; Y is -0-; -S(0)n-; -NR15-; -C(=0)-; -CH(OR15)-; -CH2-; -CH2CH2-; -CH=CH-; -C=C-; -CH20-; -OCH2-; -CH2S(0)n-; -S(0)nCH2-; or a direct bond; Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; 25 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; Cj-C3 alkyl; or cyclopropyl. Preferred 4B. Compounds of Preferred 3B wherein: R1 is methyl; 30 R2 is methyl; Y is -0-; -S(0)n-; -NR15-; -C(=0)-; -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. WO 97/00612 PCTAJS96/10326 Preferred 5B. 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 5 Y is -O-; and R9 is phenyl substituted with R11 and optionally substituted with R1-. Most preferred are compounds of Preferred 5B selected from the group: 4-[2-[[3-(3-ethynylphenyl)-l,2,4-thiadiazol-5-yl]oxv]phenyl]-2,4-dihvdro-5-methoxy-2-methyl-3//-l,2,4-triazol-3-one; and 10 [3-[5-[2-( 1,5-dihydro-3-methoxy-1 -methyl-5-oxo-4H-1,2,4-triazol-4- yl)phenoxy]-l,2,4-thiadiazol-3-yl]phenyl] trifluoromethanesulfonate. This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of Formula EB and at least one of a surfactant, a solid diluent or a liquid diluent. The preferred compositions of the present invention are 15 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 20 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. 25 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. 30 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: Wis O; R1 is C|-C3 alkyl or Cj-Cj haloalkyl; 35 R- is H; CpC6 alkyl; Cj-C6 haloalkyl; or C3-C6 cycloalkyl; and WO 97/00612 PCT/US96/10326 33 R3 and R4 are each independently halogen; cyano; nitro; C]-C6 alkyl; Cj-Cg haloalkyl; C]-C6 alkoxy; Cj-C6 haloalkoxy; C|-C6 alkylthio; Cj-C6 alkylsulfonyl; Co-Cg alkylcarbonyl; C2-C6 alkoxycarbonyl; (C]-C4 alkyl)NHC(O); (Ci-C4 alkyl^NQO); benzoyl; or 5 phenylsulfonyl. Preferred 2C. Compounds of Preferred 1C wherein: A is O or N; X is OR1 or halogen; R1 is C}-C3 alkyl; 10 R-is H or C1-C2 alkyl; and R3 and R4 are each independently halogen; Cj-C-^ alkyl; C1-C3 alkoxy; or Cj-C3 alkylthio. Preferred 3C. Compounds of Preferred 2C wherein: A is N; 15 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-dihydro-4-(2-hydroxyphenyl)-5-methoxy-2-methyl-3#-l,2,4-triazo]-3-one; 20 2,4-dihydro-4-(2-hydroxy-6-methylphenyl)-5-methoxy-2-methyl-3/f-1,2,4- triazol-3-one; 5-chloro-2,4-dihydro-4-(2-hydroxy-6-methylphenyl)-2-methyl-3/f-l,2,4-triazol-3-one; and 5-chloro-2,4-dihydro-4-(2-hydroxyphenyl)-2-methyl-3//-l,2,4-triazol-3-one. 25 Of note are embodiments where X is other than H; embodiments where R2 is H, Cj-Cg alkyl, Cj-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-Cg alkynyl, C2-Cg haloalkynyl, C3-C6 cycloalkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl; embodiments where Y is -0-, -S(0)n-, -NR15-, -C(=0)-, -CH(OR15)-, -CHR6-, -CHR6CHR6-, -CR6=CR6-, -C^C-, -CHR150-, -OCHR15-, -CHR15S(0)n-, 30 -S(0)nCHR15-, -CHR150-N=C(R7)-, -(R7)C=N-OCH(R15)-, -C(R7)=N-0-, -0-N=C(R7)-, -CHR150C(=0)N(R15)-, -CHR15OC(=S)N(R15)-, -CHR150-N(R15)C(=0)N(R15)-,-CHR150-N(R15)C(=S)N(R15)-, -CHR150-N=C(R7)NR15-, -CHR150-N=C(R7)OCH2-,-CHR150-N=C(R7)-N=N-, -CHR150-N=C(R7)-C(=0)-, -CHR15S-C(R7)=N-, -C(R7)=N-NR15-, 35 -CH=N-N=C(R7)-, -CHR15N(COCH3)-N=C(R7)-, -0C(=S)NR15C(=0)-, -CHR6-C(=W1)-A1-, -CHR6CHR6-C(=W1)-A1-, -CR6=CR6-C(=W1)-A1-, WO 97/00612 PC T/IJS96/10326 34 -C=C-C(=W')-A'-, -N=CR(i-C(=\V1 )-A'- ora direct bond; embodiments where R7 is H, C]-Cft alkyl, C|-Cg haloalkyl, CrCg alkoxy, CrC6 haloalkoxy, C(-C6 alkylthio. C|-Cg alkylsulfinyl, CpCg alkylsulfonyl, CpCg haloalkylthio, Cj-Cg haloalkylsulfinyl, Cj-Cg haloalkylsulfonyl, C2*C6 alkenyl, C2-C6 haloalkenyl, C2-Cg alkynyl, C2-C6 5 haloalkynyl, C3-C6 cycloalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, halogen, cyano or morpholinyl; embodiments where Z is other than C3-C8 cycloalkenvl 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 -CHR150-N=C(R7)-, -0-N=C(R7)-, -CH=N-N=C(R7)- or 10 -CHR15N(COCH3)-N=C(R7)-, R7 and said adjacently attached R10 are taken together as -(CH2)r-J- such that J is attached to Z; embodiments where R11 and R12 are each independently halogen, Cj-C4 alkyl, C1-C4 haloalkyl, C2-Cg alkenyl, C2-Cg haloalkenyl, C2-Cg alkynyl, C2-C6 haloalkynyl, Cj-C4 alkoxy, CVC4 haloalkoxy, C3-Cg alkenyloxy, C3-C6 haloalkenyloxy, CrC4 alkylthio, CrC4 haloalkylthio, CrC4 alkylsulfinyl, CrC4 15 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 R19, R20, R21, R22, R23, and R24 are each independently CrCg alkyl, Cj-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, Cj-Cg alkyl, Cj-Cg 20 haloalkyl, C]-Cg alkoxy, Cj-Cg haloalkoxy, Cj-Cg alkylsulfonyl, C2*Cg alkylcarbonyl, C2-Cg alkoxycarbonyl, (Cj-C4 alkyl)NHC(O), (C]-C4 alkyl)2NC(0), benzoyl or phenylsulfonyl; embodiments where Z is selected from the group 1,2,4-oxadiazolyl, I,3,4-oxadiazolyl, 1,2,4-thiadiazolyl and 1,3,4-thiadiazolyl, each group substituted with R9; embodiments where R11 is C2*Cg alkenyl, C2*Cg haloalkenyl, C2~Cg alkynyl, C2-Cg 25 haloalkynyl, C3-C6 alkenyloxy, C3-Cg haloalkenyloxy, Cj-C4 alkylthio, CrC4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C]-C4 alkylsulfonyl, CpC4 haloalkylsulfonyl, C3-C6 alkenylthio, C3*Cg haloalkenylthio or SF5; embodiments where R12 is halogen, C]-C4 alkyl, C]-C4 haloalkyl, Co-Cg alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, CrC4 alkoxy, CrC4 haloalkoxy, C3-C6 alkenyloxy, C3-C6 30 haloalkenyloxy, C ] -C4 alkylthio, C j -C4 haloalkylthio, C j -C4 alkylsulfinyl, C ] -C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C]-C4 haloalkylsulfonyl, C3*Cg alkenylthio, C3-Cg 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 35 with R9 and optionally substituted with one or more R10; and embodiments where Z is WO 97/00612 PCT/US96/10326 35 .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 5 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, R^-R-7, Y, Z1, W1, A'-A3, Z, Q, J, m, n, p, rand s in the compounds of Formulae 1-5S 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 10 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 la or lb, or both la and lb. The present invention comprises all tautomeric forms of compounds of Formula I. Y f Z Y "WH A— g A—N 15 la ft 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. 20 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, 25 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 halccarbons such as dichloromethane or chloroform. WO 97/00612 PCT/US96/10326 36 Scheme 1 E^^Z E^^Z G W I X\/-' Methods 1-4 i A— N \ , a-n r- v i I R2 1 1 x = oh, sh,nh2. x = or1,sr1.nhr1, NHfCj-Cg alkyl) or Wq-Cg alkyHR1, NH(C j-Cg alko xv) or N(C]-C^, alkoxy )R' Method 1: U-CH=N2 (U = H or (CH3)3Si) NH 5A Method 3: (R^O+BF-f 2 Method 2: Jl . ; Lewis acid ci3cr or1 3 4 Method 4: (R1)2S04; R'OSOoV; orR'-hal; optional base (hal = F, CI, Br, or I) (V= Cj-C^ alkyl, C]-^ haloalkyl, or 4-0^-0^4) For example, compounds of Formula I can be prepared by the action of diazoalkane reagents of Formula 2 such as diazomethane (U = H) or 5 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 10 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. Honig, Synth. Commun., (1990), 20, 203). Compounds of Formula I can also be prepared from compounds of Formula 1 by 15 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. Schollkopf, U. Groth, C. Deng, Angew. Chem., Int. Ed. Engl., (1981), 20,798). WO 97/00612 PCT/US96/I0326 37 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 5 additional base. Appropriate bases include alkali metal alkoxides such as potassium rerr-butoxide, inorganic bases such as sodium hydride and potassium carbonate, or tertiary amines such as triethylamine, pyridine, l,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. 10 Compounds of Formula la (compounds of Formula 1 wherein G = C, W = O 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 TV-substituted hydroxylamines (HO-NHR2) and substituted hydrazines (HN(R5)-NHR2). Examples of such nucleophiles are N-methylhydroxylamine and 15 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 = CI) using thionyl chloride or oxalyl chloride, or into the acyl imidazole (T = 1-imidazolyl) by treating with 1,1 '-carbonyldiimidazole. Scheme 2 E Z 20 E "Z | ,H HA—NHR2 6 Ho^y T T A— O 5 T = 0(C]-C4 alkyl), G, 1-iiridazolyl R-la 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 25 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 30 of Formula 5b after modification of the carboxylic acid functional group to the WO 97/00612 PCT/US96/10326 38 appropriate Y and Z group. A copper (I)-catalyzed coupling of malonates of Formula 7 with orthobromocarboxvlic 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 an (see P. Beak, V. Snieckus, Acc. Chem. Res., (1982), 15, 306 and Org. React., (1979), 26, 1 and references therein). Scheme 3 . Y. RChC CChR £ Z * ^ L-H E Z 7 C5^ ! ► 1 1 g Cul, base O OR OR 5a R = Ci-C4 alkyl A .CO2H E I .H CChH CuBr O^ ^ | NaH || Br ROoC^^CCbR 0R OR 8a 7 5b R = Cj-C4 alkyl 10 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. WO 97/00612 \ PCT/US96/10326 39 Scheme 4 O II RO^OR E 2 or E Z I ► l/H H^c-° ? N-S**0 I o/cvor I I OR • OR OR base 9 5a R = Cj-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 5 illustrated in Scheme 5 (see Org. Synth., Coll. Vol. I, (1941), 270). Additionally, esters of formula 9 can be prepared by palladium (O)-catalyzed cross coupling reaction of aryl iodides of Formula 8 with a Reformatsky reagent or an alkoxy(tria!kylstannyl)acetylene followed by hydration (Scheme 5). For example,.see T. Sakamoto, A. Yasuhara, Y. Kondo, H. Yamanaka, Synlett, (1992), 502, and 10 J. F. Fauvarque, A. Jutard, J. Organometal. Chem., (1977), 132, C17. Scheme 5 e-Y-Z h2C^ CN 10 ROH acid E Z I h2C^ I OR O ROH acid A BrZn CH7CO2R o r (1) R3SnCsCOR Pd° cat. (2) H+ E-V-Z 8 e-Y-Z h2C^ c^° I OH 11 R = C]-C4 alkyl WO 97/00612 PCT/US96/10326 40 Aryl acetic acid esters of Formula 9a can also be prepared by copper (l)-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 ^(Cl,Br,I) HY1 Z YL E E Z i 13 I h2^^O I I OR OR 12 9a R = Cj-C4 alkyl 5 Y1 = 0, S, OCHR15, SCHR15, 0-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 10 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 ^R26 12 ^ f I«—CHR15-Z; f Z o 16 "2^0 | base y OR OR 14 9b R = C]-C4 alkyl R26 = OR SH CHR15OH, CHR15SH, NHR15 Y2 = O, S, OCHR15, SCHR15, CHRlsO, CHR15S, NR15 Lg = Br, Q, I, OSO2CH3,0S02(4-Me-Ph) 15 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 WO 97/00612 PCT/US96/10326 41 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 S 0 II Z-~C"--R7 14a 7 /B Y3^ E E Z H2C^0 ^^0 I I OR OR 9e 9c B = CHR15Br R = (^-€4 alkyl 9d B = CHR15ONHo.Ha Y3 = CHR15ON=C0R7) 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 (R^O-M"1*), alkali metal thioalkoxides (R]S-M+), 10 or an amine derivative in a suitable solvent (Scheme 9). The leaving group Lg1 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 dimet'nylformamide or dimethyl sulfoxide, dimethoxyethane methanol. 15 97/00612 PCT/US96/10326 42 Scheme 9 I r'o-m+r's-m+, I G ^ G NH3,R'Nhh.R1 NH(C]-Cgalkvl), N^V A—N ^Cj-Cg alkoxy )Nhb' X-N ^r2 °r R1 NH(C j -Cg alkoxy) ^R2 17 I x=or1,sr1,nh2,nhr1. N(Cj-Cg alky 1)R', NH(C j -Cg alkoxy), or N(Cj-Cg alkoxy )R* Lg1 = a Br, -SO2V, or -OSO2V V= C]-Cg alkyl, Cj-Cg haloalkyl. or 4-CH3-CgH4 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 P-halo-substituted derivatives (Scheme 10). Alternatively, compounds of Formula lb can be treated with an alkylsulfonyl halide or haloalkylsulfonyl anhydride, such as methanesulfonyl chloride, /?-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding fi-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 E"" E"' ^Z | halogenating agent | HC> G w ► Lg2 G or VSCh-hal or ' A-N VSO2-O-O2SV A—N \ - \ -R2 R2 lb 17a Lg2 = Q, Br, or -OSO2V V = CpCg alkyl. Cj-Cg haloalkyl. or ^Q^-Cgfy hal = Br, Q or F WO 97/00612 PCT/US96/10326 43 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® (KHSO5). Scheme 11 Y Y E Z E Z | oxidizing agent | VS- VS02^/?\^0 A—N A—N \ , \ 0 R2 R2 18 17b V = C!-C5 alkyl, q-C^ haloalkyl, or4-CH3-C^H4 Alternatively, halo-compounds of Formula 17c (compounds of Formula 17a 10 wherein A = N, G = N, and W = O) can be prepared from hydrazides of Formula 19 as illustrated in Scheme 12. When R27 = C(=S)S(Cj-C4 alk>'0. 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. 15 Tarraga, 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 = CI. This procedure is described in detail in J. Org. Chem., (1989), 54, 1048. WO 97/00612 PCT/US96/10326 eaz O. .NH hn- ✓R27 -N \ rj R2 19 R27 = C(=S)S(C1-C4 alkyl) orR2 44 Scheme 12 R27 = C(=S)S(C|-C4 alkyl) S(0)(hal)n R27 = R2 COCb e-Y-Z HN ,o N N r2 hal- e-Y-Z v'V N—N R2 17c hal = Q. 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 5 Formula H2NNR2R27 in an inert solvent such as tetrahydrofuran affords the hydrazide. Scheme 13 .Y. f ~z V 21 /r27 .yv H2N—N E Z O. .NH °^n 1 k,'r27 0 HN N s , R2 19 r27 = Q=S)S(CrC4 alkyl) or R2 3) Conjugate Addition/Cvclization Procedures 10 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 WO 97/00612 PCT/US96/10326 45 Formula 22 with an ambident nucleophile of Formula 6 (Scheme 14). The nucleophiles of Formula 6 are described above. Scheme 14 E""^Z E^Y^Z \_ HA—NHR2 | Rls^c^^c^w 6 * R'SYY"' SR1 OR A—N V 22 Ic R = Cj-C4 alkyl 5 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 R'-halide, such as iodomethane or propargyl bromide (Scheme 15). Scheme 15 Y Y E Z l)CS2,base E Z ^^0 2)2equiv.R1-hal r1s> i I.I OR SR1 OR hal = Q, Br or I jq 9 R = C]-C4 alkyl 22a O 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 15 thiocarbonyl transfer reagents such as phosgene, thiophosgene, diphosgene (ClC(=0)0CCl3), triphosgene (Cl3COC(=0)0CCl3), MN'-carbonyldiimidazole, W.N'-thiocarbonyldiimidazole, and l,r-carbonyldi(l,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. 20 Appropriate bases include alkali metal alkoxides such as potassium rerr-butoxide, inorganic bases such as sodium hydride and potassium carbonate, tertiary amines such as triethylamine and triethylenediamine, pyridine, or l,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Suitable solvents include polar aprotic solvents such as acetonitrile. WO 97/00612 PCT/US96/I0326 46 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 150°C and the reaction time can be from 1 to 72 hours depending on the choice of base, solvent, temperature, and substrates. Scheme 16 xi n E^Z I* I 24 I HNsC=W optional base H2N—N N—N V V 23 Id T1 and T2 are independently Q, OOQ3. 0(Ci-C4 alkyl), l-inidazolyl, 1,2,4-triazolyI X = OHor SH X] = Oor S N-Amino-ureas of Formula 23 can be prepared as illustrated in Scheme 17. 10 Treatment of an arylamine of Formula 25 with phosgene, thiophosgene, MW-carbonyldiimidazole, or N./V'-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 JV-amino-urea of Formula 23. 15 WO 97/00612 PCT/US96/10326 47 Scheme 17 e/,nZ I NHo 25 optional base e/Y^Z 26 w r2—nh-nh2 e-Y-Z hn. HoN—N NC^W / \ o r2 23 Compounds of Formula le (compounds of Formula 1 wherein A = CR5, G = N, and X = O) can be prepared by either method illustrated in Scheme 18. Ureas of 5 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 10 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. WO 97/00612 PCT/US96/10326 E I HN 48 Scheme 18 O Y " ' T-"C"~~-CHR5 -hal 28 •c^w / HN \,2 optional base 27 R- T = Q, CKC1-C4 alkyl), or 1-inidazolyl hal = CI, Br, or I R2NHCHR5C(0)0R yr j 28a ^ C | ** optional base v W R = Ci-C4 alkyl 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 5 isothiocyanate of Formula R~N=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), 10 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, 15 1968; p 37 and Tetrahedron Lett. (1982), 23(7), 699 and references therein. WO 97/00612 PCT/US96/10326 4) Thionation Procedures Compounds of Formula le, compounds of Formula I wherein W = S, can be 5 prepared by treating compounds of Formula Id (I wherein W = O) with thionating reagents such as P2S5 or Lawesson's reagent (2,4-bis(4-methoxyphenyl)-l,3-dithia-2,4-diphosphetane-2,4-disulfide) as illustrated in Scheme 20 (see Bull Soc. Chim. Belg., (1978), 87, 229; and Tetrahedron Lett., (1983), 24, 3815). Scheme 20 P2S5 or ,G^ r' — E z O lawesson's reagent X-— A—N A-N V r2 10 Id Ie 5) Arvl Moiety (E-Y-Z) Synthesis Procedures Compounds of Formula If (compounds of Formula I wherein Y is CHR150, CHR15S, or CHR150-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 15 base, for example sodium hydride, to form the corresponding alkoxide or thioalkoxide which acts as the nucleophile. WO 97/00612 PCT/US96/10326 50 Scheme 2 1 ,CHR15(C1, Br, or D x-fy w HO-Z, or HO-N=CR7-Z, or i HS-Z; base X- A —N R2 29 frw A —N R2 If y4 = chr150, chr15o-n=cr7, chr15s Halogenation ,chr15oh ^«Y w A—N \ R2 30 Some aryl halides of Formula 29 can be prepared by radical halogenation of the corresponding alkyi compound (i.e., H instead of halogen in Formula 29), or by acidic 5 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 lg and 10 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=0 affords the olefin of Formula lg. 15 WO 97/00612 PCT/US96/10326 .CHR6(Q. Br, or I) *~«Y w a —n \ o R2 29 =C(R6)Z base 51 Scheme 22 PfQsHsb or P(OR)3 ,chr6-p' ZY w A —N R- 31: P1 =P+(C6H5)3haUde- R = Cj-C4 alkyl 32: pUp(ORb ,CR^=CR6—z ^<Y w A—N "2 \ R- lg 1) Halogenation 2) Dehalogenation Catalyst .CHR6-CHR6-Z teC—Z I f W w A—N A—N R2 V Ih L The olefins of Formula lg can be converted to the saturated compounds of 5 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 halogenation/dehalogenation of Formula lg olefins using procedures well-known in the art (March, J. Advanced Organic Chemistry; 10 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. Chem., (1975), 93 253-257). The olefin of Formula lg can also be prepared by reversing the reactivity of the reactants in the Wittig or Horner-Emmons condensation. For example, 2-alkylaryl WO 97/00612 PCT/US96/10326 52 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 5 afford the olefin of Formula lg. 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 10 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 X- ,CH2R6 fyw A—N R2 33 .CR^CR6—Z E I A—N V Ik 1)Br2orNBS 2equiv., CCI4 light *- 2) Moipholine Con. Ha H20 NBS = N-bromosuccinimide «^H5)3P=C(R6)Z 36 or ' 6 (RO)2P"C(R6)Z 37 X- R = Cj-C4 alkyl J2 = O, S hal = F, CI, Br, I ,CR6J] A—N V 34: J1 =Br2 35: J1 =(=0) Base 9 hal (RO)2P-CHC-OZ J* 37a: J2=0 37b: J2 = S J2 R6 I II ,c=c-c-oz I X- | hal w A—N R2 Ij wo 97/00612 pct/us96/10326 53 Oximes of Formula Ik (Formula I wherein Y is C(R7)=N-0) can be prepared from carbonyl compounds of Formula 38 by condensation with hydroxylamine, followed by O-alkylation with electrophiles of Formula Z-(C1, Br, or I) (Scheme 24). Alternatively, 5 the O-substituted hydroxylamine can be condensed with the carbonyl compound of Formula 38 to yield oximes of Formula Ik directly. Scheme 24 ^cr7=0 l)h2n-oh cr7=n-oz f 2)Z-hal | or w / h2N-OZ \\ / A —N A —N V R2 38 hal = Q, Br or I K 10 Carbamates of Formula II 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 II can be further alkylated to provide the carbamates of Formula Im. WO 97/00612 PCT/US96/10326 54 Scheme 25 0 II E^CHR15OH GIRl50/CXNH2 I 39 H ,g. I X^f Yw A —N \\ / 30 base W \ 0 A—N R2 \ 0 R2 D O x ^CHR150 N-Z E I ,, r!5- hal | Rl5 xlVw R2 hal = C1, Br or I A N\ Im Compounds of Formula I wherein Y is -CHR^O-N^CR^-Q-N-A-^-Z^-A1-, -CHRI50-N=C(R7)-C(R7)=N-A2-A3- or -CHR150-N=C(-C(R7)=N-A2-Z1)- can be 5 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 -CHR150C(=0)0-, -CHR150C(=S)0-, -CHR150C(=0)S-, -CHR15OC(=S)S-, -CHR15SC(=0)N(R15)-, 10 -CHR15SC(=S)N(R15)-, -CHR15SC(=0)0-, -CHR15SC(=S)0-, -CHR15SC(=0)S-, -CHR15SC(=S)S-, -CHR15SC(=NR15)S- or -CHR15N(R15)C(=0)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. 15 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 20 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 WO 97/00612 PCT/U S96/10326 55 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. 5 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 = 0-N=C(R7) and in Scheme 21, 10 reagent HO-N=CR7. Scheme 26 H->NOHor 0=CR>-Z HoNOH'HQ/base* HO-N=CR'-Z 40 41 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. 15 "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 Chemistry, 3rd ed., John Wiley: New York, (1985), pp 433-435 and references therein.) The organometallic compounds of 20 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 25 corresponds to 0=C(R6)Z in Scheme 22. WO 97/00612 PCT/US96/10326 56 Scheme 27 o=cr28-z 40 R28=R7 40a R28=R6 o=cr28-z 40 R^=R7 40a R28=R6 hal=Q, Br, 1 M'=MgX CuLiZ CdZ SnR3 R = C]-C4 alkyl 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 5 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 S02Cl2, 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 free-radical halogenation, see Huyser, 10 in Patai," The Chemistry of the Carbon-Halogen Bond," Part 1, 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, CI, or I and reagent Z-hal in Scheme 24. Compounds of Formula 47 can be prepared from 15 compounds of Formula 46 by similar procedures. Compounds of Formula 47 correspond to compounds cf Formula 16 in Scheme 7 where Lg = Br, CI, 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, "Organophosphorous Reagents in Organic 20 Synthesis," Academic Press, New York (1979) for a general treatise on these reagents. T3=C1 OCOR28 OR NRo R28=R6orR7 WO 97/00612 PCT/US96/10326 Z-H hah, g , orr-BuO-hal Z-hal 39a *- 43 or SO2CI2 optional catalyst hal = Q, Br, I H-CHR6-Z 46 R = Cj-C4 alkyl hal-CHR6-Z 47 1)(C6H5)3P or CRO)3P ^ 2) base 36 or 37 in Scheme 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 5 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 Y1 = O and reagent HO-Z in Scheme 21. Compounds of Formula 52 can be prepared from compounds of Formula 48 by conversion to the 10 dialkylthiocarbamates of Formula 50 followed by rearrangement to Formula 51 and subsequent hydrolysis. See M. S. Newman and H. A. Kames, J. Org. Chem. (1966), 31, 3980-4. Formula 52 corresponds to Formula 13 in Scheme 6 when Y1 = S and reagent HS-Z in Scheme 21. WO 97/00612 PCT/US96/10326 58 Scheme 29 0=C(CH3)-Z 1) [O] +- HO-Z 2) hydrolysis ClCSN(Rb hp„, HO-Z =—»- Z-0-CSN(R)2 neat » Z-S-CON(R)2 >■ HS-Z 49 50 51 52 R = Cj-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 5 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 10 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 HNOo 7,N-i+ Z-NHn *L 2 CuBr. CuG or I" *■ 54 ^ Z-hal hal=Br, CI, 1 53 CuoO CufNC^ 43 HO-Z 48 (S2) - r* HS-Z 52 15 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 Niiration," 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), WO 97/00612 PCT/US96/10326 59 pp 1 103-4 and references therein). Formula 53 corresponds to Formula 13 in Scheme 6 when YJ=NRl5 and RI5 = H. Scheme 31 Z-H 39a Z-NOo 55 Z-NH2 53 5 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 10 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 15, 300 (Scheme 32). Scheme 32 -T4 E I H 56 Organolithium reagent, ,T^ T4 = CC^H, CONR2, CONHR, O CSNHR, CHoOH, OMe, CObOMe Functional I Group __ Interconversion o7 ,T5 58 Y-Z construction E^Z 8 T5 = CHR6(C1, Br.D.CHO CH2OH,OH R = CJ-C4 alkyl t = 1 or 2 WO 97/00612 PCT/IJS96/10326 60 Compounds of Formula In (Formula IA where Y is (CHn)xO, where x = 0 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 5 (for example, K2CO3, KO-r-Bu or NaH) in suitable solvents (for example, acetone, dimethylformamide, dimethyl sulfoxide or tetrahydrofuran) (see Scheme 33). Scheme 33 OH / ■(CH2)X c^,rw A—N \ R2 Lg-Z base, solvent E I ,G A—N OZ / ■(CH2)X w R2 59 where x = 0or 1 In 10 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), 55,469 or J. Het. Chem. (1979), 961 for the preparation of 1,2,4-thiadiazoles, U.S. 5,166,165 or 7. Chem. Soc., Perkin Trans. 1 (1983), 967 for the preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles, EP 446,010 15 or J. Med. Chem. (1992), 55, 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. 20 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 25 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 WO 97/00612 PCT/US96/10326 61 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 5 compounds of Formula I. One skilled in the ait 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 substituenrs or modify existing substituents. 10 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. Pails and percentages 15 for chromatographic solvent mixtures are by volume unless otherwise indicated. 'H 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 20 Step A: Preparation of /V-^-methoxyphenvP^^-dimethvIhvdrazinecarboxamide 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-dimethylhydrazine 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 25 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. NMR (CDC13) 5 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-dihvdro-4-(2-methoxvphenvlV2-methvl-3/7- 30 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 35 distilled water, and then with saturated aqueous sodium chloride solution. The organic layer was dried (MgSO.4), filtered, and concentrated under reduced pressure. The solid WO 97/00612 PCT/US96/10326 62 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. "H NMR (CDC13) 8 7.45 (t,lH),7.25 (d.lH), 7.05 (m,2H), 3.84 (s,3H), 3.53 (s,3H), 5 Step C: Preparation of 5-chloro-2.4-dihvdro-4-(2-hvdroxvphenvlV2-methvl- 3//-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 10 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 IN aqueous sodium hydroxide solution. The aqueous layer was acidified with 6N aqueous hydrochloric acid solution and extracted with dichloromethane and then with ethyl acetate. The organic 15 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 (CDCI3) 6 8.18 (s,lH), 7.11 (t,2H), 6.91 (UH), 6.76 (d,lH), 3.56 (s,3H). Step D: Preparation of 2.4-dihvdro-4-(2-hvdroxyphenvl)-5-methoxv-2-methvl- 20 3H-\ .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 25 the product was extracted using IN aqueous sodium hydroxide solution. The aqueous layer was acidified with 6N aqueous hydrochloric acid solution and extracted with dichloromethane. The organic layer was dried (MgSC^), 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). !H NMR (CDCI3) 30 5 8.40 (br s,lH), 7.20 (m,2H), 7.03 (d,lH), 6.94 (UH), 4.00 (s,3H), 3.48 (s,3H). Step E: Preparation of 4-r2-rf3-r3.5-bis('trifluoromethvl')phenvll-1.2.4-thiadiazol-5-vlloxv1phenvn-2.4-dihvdro-5-methoxv-2-methv)-3//-1.2.4-triazol-3-one To a solution of 5-chloro-3-[3,5-bis(trifluoromethyl)phenyl]-l,2,4-thiadiazole (0.8 g, 2.4 mmol, available from Maybridge, Catalog No. RDR03892) in DMF (8 mL) 35 was added the title compound of oicp rj ^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 WO 97/00612 PCT/US96/10326 63 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 5 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. IH NMR (CDC13) 5 8.36 (s,2H), 7.94 (s,lH), 7.60 (m,2H), 7.50 (d,2H), 3.81 (s,3H), 3.37 (s,3H). 10 EXAMPLE 2 Step A: Preparation of ethvl 3-(trifluoromethoxv)benzenecarboximidate hydrochloride To a solution of 3-(trifiuoromethoxy)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 15 saturated with dry HC1 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. NMR (Me2SO-c/6) 5 8.2 (m,lH), 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-(trifluoromethoxv)benzenecarboximidamide 20 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). NMR (Me2SO-d6) 5 9.4-8.8 (br,4H), 8.01 (m,lH), 7.97 (m,lH), 7.81 25 (m,2H). Step C: Preparation of 5-chloro-3-f3-(trifluoromethoxv)phenvIl-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 30 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 35 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 WO 97/00612 PCT/US96/10326 64 is used without further purification. 'H NMR (CDCI3) 5 8.18 (d,lH), 8.11 (sJH), 7.49 (t.lH), 7.34 (m.lH). Step D: Preparation of 2.4-dihvdro-5-methoxy-2-methvl-4-f2-rf3-f3- (trifluoromethoxy^phenvll- 1.2.4-thiadiazol-5-yHoxv1phen\'n-3/y-1.2.4-5 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 10 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 15 compound of Step D, a compound of the invention, as an off white solid melting at 112-113 °C. IH NMR (CDCI3) 8 8.10 (d,lH), 8.05 (s,lH), 7.6-7.4 (m,5H), 7.27 (m,lH), 3.79 (s,3H), 3.37 (s,3H). EXAMPLE 3 Step A: Preparation of 2-(4-chlorophenvP-5-(methvlthio)-l .3.4-oxadiazole 20 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 25 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-(4-chlorophenvl')-5-('methvlsuIfonvl')-l .3.4-oxadiazole To a solution of the title compound from Step A (17.69 g, 78.1 mmol) in acetic 30 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. NMR (CDCI3) 8 8.70 (m,2H), 7.57 (m,2H), 3.53 (s,3H). WO 97/00612 PCT/DS96/S 0326 65 Step C: Preparation of 4-f2-lT5-(4-chlorophenvn- 1.3.4-oxadiazol-2- vnoxvlphenvP-2.4-dihvdro-5-methoxv-2-rnethvl-3f/-l .2.4-triazoI-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 rng) and the title compound of 5 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 10 the invention, as a solid melting at 130-132 °C. lH NMR (CDC13) 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-dihvdro-4-r2-r(3-iodo-1.2.4-thiadiazol-5-vl)oxv1phenvll-5-methoxv- 2-methvl-3//-l .2.4-triazol-3-one 15 To a solution of the title compound of Step D in 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 20 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. NMR (CDC13) 5 7.55 (m,2H), 7.46 (m,2H), 3.86 (s,3H), 3.40 (s,3H). EXAMPLE 5 Preparation of 4-f2-[T3-('3.3-dimethyl-l-butvnvD-l.2.4-thiadiazoi-5-vlloxvlphenvll-2.4-25 dihvdro-5-methoxv-2-met'nvl-3//-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 rnL), 3,3-dimethyl-l-butyne (0.219 mL) and bis(triphenylphosphine)palladiiim(II) chloride (25 mg). The mixture was stirred for 40 h at ambient temperature before being diluted with ethyl 30 acetate, washed with IN HC1 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. 'H NMR (CDCI3) S 7.55 (m,2H), 7.45 (m,2H), 3.83 (s,3H), 3.39 (s.3H). 1.32 <s,9H). WO 97/00612 PCT/US96/10326 66 EXAMPLE 6 Preparation of 2.4-dihvdro-5-methoxv-2-methvl-4-[2-fr3-f3-f'trimethvlsilvDeihynyllphenvn-1.2.4-thiadiay.ol-5-vl|o\v1phenvn-3//-1.2.4-triazol-3-one To a solution of 2,4-dihydro-4-[2-[[3-(3-iodophenyl)-1,2,4-thiadiazol-5-5 yl]oxy]phenyl]-5-methoxy-2-methyl-3/f-l,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 10 being diluted with ethyl ether. The resulting mixture was washed with a saturated aqueous solution of ethylenediaminetetraacetic acid, a saturated aqueous solution of NaHC03, and a saturated aqueous solution of NaCl 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 15 melting at 133-134 °C. IH NMR (CDC13) 5 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-r2-rf3-r3-ethvnvlphenvl)-1.2.4-thiadiazol-5-vlloxy1phenvll-2.4-dihvdro- 5-methoxv-2-methvl-3/7-1.2.4-triazol-3-one 20 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 25 afforded the title compound of Example 7 (153 mg), a compound of the invention, as a white solid melting at 177-178 °C. NMR (CDC13) 5 8.29 (s.lH), 8.15 (d.lH). 7.62 (m.lH). 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-f5-chloro-1.2.4-thiadiazol-3-vl)pheno! 30 To a solution of 3-chloro-5-(3-methoxvphenyl)-l ,2,4-thiadiazole (prepared from 3-methoxvbenzonitrile according to the procedure described in Step C in Example 1) (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 NaHCOj was added and the 35 mixture was extracted with ethyl ether and the extract was dried over magnesium sulfate. Purification by column chromatography (silica gel, 20% and then 409c ethyl ether in WO 97/00612 PCT/US96/J 0326 67 petroleum ether) gives the title compound of Step A. 'H NMR (CDCI3) 5 7.85 (d.lH), 7.73 (s.lH), 7.36 (t.lH), 6.95 (d,lH), 5.42 (s.lH). Step B; Preparation of f 3-f5-f2-( 1.5-dihvdro-3-methoxv- l-methvl-5-oxo-4/f- I.2.4-tria2ol-4-yl)phenoxv1-1.2.4-thiadiazol-3-vllphenvIl ben?oate 5 To a solution of the title compound of Step A (7.15 g, 33.6 mmol) ir. methylene chloride (112 mL) was added triethylamine (6.1 mL), 4-(dimethylamino)pvridine (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. HC1 (1 N aqueous solution) was then added and the mixture was extracted with ethyl ether 10 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 D in 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. 15 Purification by column chromatography (silica gel, 1% and then 2% methanol in methylene chloride) gave the title compound of Step B (lO.lg), a compound of the invention. *H NMR (CDCI3) 5 8.21 (d,2H), 8.1 (d,2H), 7.7-7.4 (m.9H), 3.77 (s,3H), 3.37 (s,3H). EXAMPLE 9 20 Preparation of 2.4-dihvdro-4-r2-IT3-(3-hvdroxyphenvl)-1.2.4-t.hiadiazol-5- vHoxv1phenvn-5-methoxv-2-methvl-3fl-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 25 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. •H NMR (CDCI3) 6 7.7 (d,lH), 7.6-7.4 (m,5H), 7.25 (m,lH), 6.9 (ddJH), 6.75 (s,lH). 30 3.80 (s,3H), 3.34 (s,3H). EXAMPLE 10 Preparation of f3-f5-f2-f 1.5-dihvdro-3-methoxv-l-methvl-5-oxo-4fM.2.4-triazol-4-vDphenoxvl-1.2.4-thiadiazol-3-vllphenvl1 trifluoromethanesulfonate To a solution of the title compound of Example 9 (0.2 g, 0.5 mmol) in methylene 35 chloride (2.5 mL) was added pyridine (0.061 mL), trifluoromethanesulfonic anhydride (0.102 mL) and a catalytic amount of 4-(dimethylamino)pyridinc. The reaction mixture WO 97/00612 PCT/US96/10326 6S was stirred for 3 days before being diluted with methylene chloride and washed with HC1 (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 while solid. 'H NMR (CDCI3) 5 8.2 (d,lH), 8.1 (s,lH), 7.65-7.45 (m,5H), 5 7.35 (dd,lH), 3.80 (s,3H), 3.37 (s,3H). EXAMPLE 11 Step A: Preparation of 2-furancarboximidamide (See Teir. 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 10 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 15 of Step A (4.01 g). NMR (Me2SO-rf6) 8 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-f2-furanvl')-1-2.4-thiadiazoIe 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 20 (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 25 chromatography (petroleum ether and then 1-chlorobutane) gave the title compound of Step B. 'H NMR (CDCI3) 8 7.6 (m,lH), 7.19 (m,lH), 6.57 (m.lH). Step C: Preparation of 4-r2-fr3-f2-furanvn-1.2.4-thiadiazol-5-vnoxy1phenvn-2.4- dihvdro-5-methoxv-2-methvl-3//-1.2.4-tria7.ol-3-one To a solution of the title compound of Step D in Example 1 (355 mg, 30 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 35 compound of Step C (213 mg), a compound of the invention, as a solid melting at WO 97/00612 PCT/US96/10326 69 107-108 °C. !H NMR (CDC13) 5 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 4-12-1 r3-("5-bromo-2-thienvn-1.2.4-thiadiazo]-5-vnoxy]phenvn-2.4-5 dihvdro-5-methoxv-2-inethvl-3//-1.2.4-triazol-3-one To a solution of 5-chloro-3-(2-thienyl)-l,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 10 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. 15 *H NMR (CDCI3) 5 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)-l,2.4-thiadia2ole A solution of 5-chloro-3-(3-thienyl)-l,2,4-thiadiazole (prepared from 3-20 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 NaHC03 and dried over magnesium sulfate. Concentration yielded the title compound of Step A (1.87 g). JH NMR (CDC'l3) 5 7.45 25 (s,lH). Step B: Preparation of 4-f2-[T3-(2.5-dichloro-3-thienvl)-1.2.4-thiadiazol-5- vnoxv1phenvl1-2.4-dihydro-5-methoxv-2-methvl-3//-1.2.4-tria2ol-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 30 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 35 and the residue was purified by crystallization from ethanol. The mother liquor was concentrated and purified by column chromatography (silica gel, 609c and then 80% WO 97/00612 PCT/US96/10326 70 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. 'H NMR (CDCI3) 5 7.65 (d,lH), 7.6-7.5 (m,lH), 7.5-7.4 (m.2H), 7.37 (s,lH), 3.SI (s,3H), 3.39 (s,3H). EXAMPLE 14 5 Step A: Preparation of 2.2-dimethylpropanimidic acid hydrochloride To a solution of trimethvlacetonitrile (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 HC1 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) 10 as a white solid. >H NMR (Me2SO-</6) 5 11.4 (br s, 2H), 4.4 (q,2H), 1.22 (s,9H), 1.05 (t,3H). Step B: Preparation of 2.2-dimethvlpropanimidamide 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 15 for 3 days before being concentrated to give the title compound of Step B (33.15 g) as an off white solid. 'H NMR (Me^SO-rfg) 5 1.25 (s,9H). Step C: Preparation of S-chloro-S-fl.l-dimethvlethyP-l^^-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, 20 36.61 mmol) and the mixture is cooled in an ice bath. Wkn 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 25 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. lH NMR (CDCI3) 6 1.42 (s,9H). Step D: Preparation of 4-f2-rf3-( 1.1 -dimethvlethvD-1.2.4-thiadiazol-5- 30 ylloxvlphenvll-2.4-dihvdro-5-methoxv-2-methvl-3//-1.2.4-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 35 was dried over magnesium sulfate and conccntrated. Purification by column chromatography (silica gel, 40%, then 60%. and then 80% ethyl ether in petroleum WO 97/00612 PCT/US96/10326 71 ether) yields the title compound of Step D (0.19 g), a compound of invention, as an off white solid melting at 110-111 °C. 1H NMR (CDC13) 5 7.5S (d, 1H), 7.50 (m, 1H). 7.47 (m.lH), 7.44 (m,lH), 3.78 (s,3H), 3.40 (s,3H), 1.36 (s,9H). EXAMPLE 15 5 Preparation of 4-r2-f(6-chloro-2-pvrazinyl)oxvlphenvll-2.4-dihvdro-5-methoxv-2- methvl-3//-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 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 15 compound of invention, as a white solid melting at 135-137 °C. NMR (CDC13) 5 8.30 (m,2H), 7.50 (m,lH), 7.40 (m,3H), 3.81 (s,3H), 3.33 (s,3H). EXAMPLE 16 Preparation of 2.4-dihvdro-5-methoxy-2-methvl-4-r2-[T6-f4-(trifIuoromethyl')phenvn-2-pvrazinvnoxy1phenvll-3f/-1.2.4-triazol-3-one 20 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 25 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 Celite®, dried over anhydrous potassium carbonate, and concentrated under reduced pressure to give a crude product. Flash column chromatography (gradient 30 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. !H NMR (CDCI3) 8 8.79 (s.lH), 8.39 (s.lH), 7.98 (d,2H), 7.67 (d,2H), 7.51 (ni.lH), 7.41 (m.3H), 3.65 (s,3H), 3.31 (s,3H). WO 97/00612 PCT/US96/10326 72 EXAMPLE 17 Preparation of 4-f6-f2-( 1.5-dihvdro-3-methoxv-1 -methvi-5-oxo-4/7-1.2.4-triazol-4- ynphenoxy1-2-pvra2invllbenzonitrile To a solution of the title compound of Example 15 (333 mg, 1.0 mmol) and 5 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 10 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 15 compound of invention, as a white solid (230 mg) melting at 195-199 °C. NMR (CDC13) 6 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-chlorophenvl)-1.3.4-thiadiazol-2-amine 20 The title compound was prepared according to Zubets, I. V.; Boikov, Yu. A.; Viktorovskii, I. V.; V'yunov, K. A.; Chem. Hct. 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. 'H NMR (MeoSO-^) 5 7.82-7.54 (AA'BB', 4H), 7.48 (s, 2H). Elemental analysis: (Calculated) C: 44.97, H: 3.77, 25 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-chIorophenvl)-1.3.4-thiadiazole The title compound was prepared according to Zubets, I. V.; Boikov, Yu. A.; Viktorovskii, I. V.; V'yunov, K. A.; Client. 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 30 which was used without further purification. 'H NMR (Me2SO-^6) 5 8.02-7.67 (AA'BB', 4H). Step C: Preparation of 4-f2-ff5-(4-chlorophenvl')-1.3.4-thiadiazol-2- ylloxylphenvn-2.4-dihvdro-5-methoxv-2 methvl-3//-1.2.4-triazol-3-one The title compound of Step B (0.46 g. 2 mmol), the title compound of Step D in 35 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 WO 97/00612 PCT/US96/10326 73 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 IN sodium hydroxide (2x20 mL) and 5 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/l) afforded the title compound of Step C, a compound of invention, as a white solid. NMR (Me2SO-d6) 5 7.92-7.45 (m,8H), 3.79 (s,3H). 3.25 (s.3H). 10 EXAMPLE 19 Step A: Preparation of 4-f3-(trifluoromethvl')phenvn-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 15 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 20 into ethyl acetate. The ethyl acetate solution was washed with water and saturated aqueous NaCl. The ethyl acetate solution was then dried over MgS04 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. 'H NMR (CDC13) 5 8.05 (s.lH), 7.95 (d,lH), 7.5 (m,2H), 6.8 (s,lH), 5.15 (br s.2H). 25 Step B: Preparation of 5-bromo-4-f3-(trif1uoromethvPphcnvn-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 30 resulting residue was partitioned between 150 mL of ethyl acetate and 100 mL of saturated aqueous NaHC03 and the mixture was stirred for 0.5 h. The organic layer was separated, washed with saturated aqueous NaCl, dried over MgS04 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 35 white solid melting at 96-98 °C. 'H NMR (CDC13) 5 8.15 (s.lH), 8.05 (d.lH), 7.65 (d,lH), 7.55 (t.lH), 5.75 (brs,2H). WO 97/00612 PCT/US96/10326 74 Step C: Preparation of 5-hromo-2-chloro-4-f3-(trifluoromethvl)phenvnthiazole 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 /err-butylnitrite (dropwise). Nitrogen evolution was evident and the reaction 5 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 IN aqueous HC1, water, and then saturated aqueous NaCl. The organic layer was dried over MgS04 and then was concentrated under reduced pressure to give a dark oil/solid residue. The main 10 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. ]H NMR (CDC13) 5 8.2 (s,lH), 8.15 (d.lH), 7.65 (d.lH), 7.6 (t,lH). Step D: Preparation of 4-[2-ir5-bromo-4-r3-(trifluorornethvnphenvIl-2-15 thiazolvlloxv1phenyn-2.4-dihydro-5-methoxv-2-methvl-3/f-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 20 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 MgS04, and then concentrated under reduccd 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 25 compound of the invention, as a gum. !H NMR (CDCI3) 8 8.2 (s.lH), 8.1 (d.lH). 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-methoxv-2-methvl-4-[2-ff4-f3 -ftrinuoromethyl')phenvll-2-thiazolvlloxvlphenvn-3fM.2.4-triazol-3-one 30 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 Celite® 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. 35 washed with distilled water and then with saturated aqueous NaCl. The organic layer was dried over MgS04 and then was concentrated under reduced pressure to give an oil. WO 97/00612 PCT/lJS96/t0326 75 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 5 at 116-118 °C. NMR (CDCI3) 5 8.05 (s.lH), 7.95 (d,lH), 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-methoxv-2-methvl-4-f2-rr5-methvl-4-r3-(trifluoromethvDphenvn-2-thia2:olvnoxvlphenvl]-3//-1.2.4-triazol-3-one 10 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 Nt 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 15 2 h at ambient temperature. The reaction mixture was diluted with diethyl ether and washed with distilled water and saturated aqueous NaCl. The orgamic layer was dried over MgSC>4 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. 20 NMR (CDCI3) 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 /V-(2-meihoxv-6-methvlphenvn-2.2- dimethvlhvdrazinecarboxamide 25 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 wanned 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 30 isocyanate as a dark red liquid which was redissolved in ethyl acetate (1 L) and cooled to 0 °C. 1, l-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. 35 lHNMR (CDCI3) 57.58 (brs.lH), 7.10 (t,lH), 6.84 (d,lH), 6.74 (d.lH). 5.22 (brs.lH), 3.80 (s,3H). 2.63 (s.6H), 2.31 (s.3H). WO 97/00612 PCT/US96/10326 76 Step B: Preparation of 5-chloro-2.4-dihvdro-4-(2-methoxv-6-methvlphenvn-2- methyl-3#-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 5 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 10 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 (CDQ3) 5 7.34 (t,lH), 6.93 (d,lH), 6.85 (d,lH), 3.79 (s,3H), 3.54 (s,3H), 2.20 (s,3H). Step C: Preparation of 5-chloro-2.4-dihvdro-4-(2-hvdroxv-6-methvlphenvl')-2- methyl-3#-1.2.4-triazoi-3-one 15 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 NaCl, dried 20 (MgS04), 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. NMR (CDC13) 6 8.11 (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-dihvdro-4-(2-hydroxv-6-methvlphenvn-5-methoxv-2- 25 rnethvl-3//-1,2.4-triazol-3-one To a stirred solution of the title compound of Step C (133.5 g, 557.0 mmo!) 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. 30 The aqueous layer was acidified (pH 4-5) with IN HC1 and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous NaCl, dried (MgSC^), 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. 'H NMR (Me2SO-rf6) 6 9.91 (s,lH), 7.17 (t.lH),6.78 (m,2H), 35 3.84 (s.3H), 3.30 (s.3H). 2.03 (s,3H). WO 97/00612 PCT/US96/10326 77 Step E: Preparation of 4-f2-r[3-f3.5-his( trifluoromethvl iphenvl 1- 1.2.4-thiadiazol- 5-vllo,\vl-6-methylphenvll-2.4-dihvdro-5-methoxv-2-mclhvl-3f/-1.2.4-triazol-3-one To a solution of 5-chloro-3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-thiadiazole 5 (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 th? 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 10 (MgS04), 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. JH NMR (CDCI3) 5 8.64 (s,2H), 7.95(s,lH), 7.50 (t,lH), 7.42 (d,lH), 7.37 (d,lH), 3.80 (s,3H), 3.39 (s,3H), 2.33 (s,3H). 15 EXAMPLE 23 Step A: Preparation of 2.4-dihvdro-5-methoxy-2-methyl-4-r2-fftrisf 1 -methvlethvnsilvlloxvlphenvn-S//-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 20 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 NaCl, dried (MgSC>4), filtered and concentrated to an oil which was purified by flash column 25 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. >H NMR (CDCI3) 5 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-f2-ethvl-6-fftrisf 1 -methvlethvDsilvlloxvlphenvll-2.4-dihvdro-5-methoxv-2-methyl-3//-1.2.4-triazol-3-one 30 A solution of the title compound of Step A (2.16 g, 5.72 mmol) in anhydrous tetrahydrofuran was cooled to -78 °C and ;er/-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 35 with aqueous ammonium chloride and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous NaCl. dried (MgS04), WO 97/00612 PCT/US96/10326 78 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 ns a white solid melting at 90-92 °C. >H NMR (CDC13) 5 7.23 (t.lH), 6.90 (d, IH), 6.77 (d.lH), 3.89 (s,3H), 3.43 (s.3H). 2.53 (q,2H), 1.24 (m, 3H), 1.15 (t,3H), 1.04 (m,18H). 5 Step C: Preparation of 4-f2-fr3-f3.5-bis(trifluoromethvnphenvn-1.2.4-thiadiazol- 5-ynoxv1-6-ethvlphenyn-2.4-dihvdro-5-methoxv-2-methvl-3f/-1.2.4-triazol-3-one The title compound of Step B (0.244 g, 0.60 mmol) and 5-chloro-3-[3,5-bis(trifluoromethyl)phenyl]-l,2,4-thiadiazole (0.200 g, 0.60 mmol) was dissolved in 10 anhydrous tetrahydrofuran (10 mL). A solution of tetrabutylammonium fluoride (0.70 mL, 1.0M 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 NaCl, dried (MgS04), filtered and concentrated. The residue 15 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. NMR (CDC13) 5 8.64 (s,2H), 7.94 (s,lH), 7.56 (t, IH), 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 20 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 NOi = nitro. TABLE 1 Compounds of Formula IA defined as: O— N O MeO^^/ R9 N B9 2-Br-Ph 2-CN-Ph 2,4-diCl-Ph 2-CF3-Ph E9 2-Me-Ph 2-F-Ph 2-Me-4-CI-Ph 3,5-diCI-Ph E9 4-EtO-2-pyrimidinyl 4,6-diMeO-2-pvrimidinyl 4,6-diMe-2-pyrimidinyl 6-CF3-4-pyrimidinyl WO 97/00612 PCT/US96/10326 79 2-I-PIi 3,5-diCF3-Ph 4-pyrimidinvl 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-pyridiny! 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-r-Bu-Ph 4-OCF2H-Ph 4-f-Bu-2-pyridinyl 3-/-Bu-Ph 4-CN-Ph 3-Me3Si-Ph 4-Me3 S i - 2-py ridiny 1 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-lhienyl 4-F-Ph 5-F-3-CF3-Ph Ph (2-CN-Ph)CH2 3-Cl-Ph 3-Br-Ph 3-1-Ph 4-I-Ph r-Bu TABLE 2 Compounds of Formula IA defined as: "O -N y N -R9 MeO^^N^O N—N \ Mc 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-CI-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-C!-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-thienyI 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph WO 97/00612 PCT/US96/10326 2-Br-Ph 2-CN-Ph 2,4-diCI-Ph 2-CFj-Ph 2-1-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-Cl-2-Me-Ph 3-/-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCl-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thienyl 4,5-diCI-2-thicnyl 4,5-diF-2-thienyl 3,4,5-triCl-2-thienyl 3-(OCH)-Ph 4-(C=CH)-Ph 2-CF3CH20-5-pyridinyl 4-CI-benzyl 2-Et-Ph 2-Cl-Ph 80 4-SCF2H-Ph 2-Nle-Ph 2-F-Ph 2-Me-4-Cl-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-r-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMc-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-CI-benzyl 2-Cl-benzyl 2-CN-benzyl 3-(Me3Si-CsC)-Ph 4-(Me3Si-CEC)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyri midi ny 1 4.6-diMeO-2-pyrimidiryl 4,6-diMe-2-pyrimidinyl 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-f-Bn-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-MeO-2-pyridinyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-r-Bu-2-pyridinyl 4-Me3Si-2-pyridiny! 4-Mc3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtO-Ph 4-I-Ph 3-COoMc-Ph 3-C02*f-Bu-Ph 3-C02Et-Ph WO 97/00612 PCT/US96/10326 81 TABLE 3 Compounds of Formula IA defined as: R9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-CI-4-Me-Ph 3,5-diF-Ph 3-F-4-CI-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diCI-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-Ci-Ph 3-Me-Ph 3-CF3-Ph 3-CI-2-Me-Ph 3-r-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCl-Ph 3.4-diCF3-Ph 0' MeO-^/ N^o N—N Me B9 4-Ph-Ph 4-Br-3~Me-Ph 3-Br-4-Me0-Ph 5-F-2-thienyl 5-Br-2-thienyl 5-Cl-2-thienyl 2,5-diF-3-thienyl 2,5-diCl-3-thienyl 2,5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Me-4-Cl-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-i-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMc-Ph -N O R9 R9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-ihienyl 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-/-Bu-Ph 4-C02Ht-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3*3-pyridinyl 3-MeO-2-pyridi nyl 5-CN-2-pyridinyl 6-Me-2-pyridinvl WO 97/00612 PCT/US96/10326 82 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F 3-CF3-Ph 4-r-Bu-2-pvridinyl 2-Br-5-pvridinyl 3-CI-benzyl 4-Me-;Si-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 3-0S02CF3-Ph 4-I-Ph 2-CF3CH20-5-pyridinyl 4-0S02CF3-Ph 3-C02Me-Ph 4-C!-benzyl 4-Et0-2-pyrimidi nyl 3-C02-/-Bu-Ph 2-Et-Ph 4,6-diMeO-2-pyrimidinyl 3-C02Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl TABLE 4 Compounds of Formula IA defined as: I A y—R9 N MeO— N—N \ Me R9 R9 B9 B9 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-pyrimidiny) 6-CF3-4-pyrimidinyl 2-i-Ph 3,5-diCF3-Ph 4-pyrimidinyl 4-CF3-2-pyridinyl 4-N02-Ph 2-MeO-Ph 4-Me0-2-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 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 3-0CF2H-Ph 3,5-diBr-Ph 3-CI-2-Mc-Ph 4-/-Bu-Ph 4-OCF2H-Ph 4-r-Bu-2-pyridinyl WO 97/00612 PCT/US96/10326 83 3-/-Bu-Ph 4-CN-Ph 3-Me3Si-Ph 4-Me-?Si-2-pyridinyl 3-F-Ph 4-N02-Ph 4-Me?Si-Ph 4-Mcr-}Ge-2-pyriuinyl 4-CF3-Ph 3,4-diMe-Ph 3-Me-^Ge-Ph 4.6-diCF3-2-pynmidinv 3.4-diCi Ph 3,5-diMe-Ph 4-Ms^Ge-Ph 5-CF3-2-l"uranyl 3,4-diCF3-Ph 4-F~3-CFvPh 3-EtO-Ph 5-CF3-2-thienyl 4-F-Ph 5-F-3-CF3-Ph Ph f2-CN-Ph)CH2 3-Cl-Ph 3-3r-Ph 3-I-Ph 4-1-Ph /-Bu TABLE 5 Compounds of Formula LA. defined as: MeO^ o—\ Me E9 R9 E9 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-pvrimidinyl 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-pyrimidiny! 2-I-Fh 3,5-diCF3-Ph 4-pyrimidinyl 4-CF3-2-pyridinyl 4-N02-Ph 2-McO-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-McO-2-pyridinyl 4-Cl-Ph 4-Br-Ph 5-Me-2-furanyI 5-CN-2-pyridinyl 3-Me-Ph 3-El-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-f-Bu-Ph 4-OCF2H-Ph 4-r-Bu-2-pyridinyl 3-r-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-furanvl 3,4-diCF3-Ph 4-F-3-CF3-Ph 3-EtO-Ph 5-CF3-2-thienv| WO 97/00612 PCT/US96/10326 84 4-F-Ph 3-CI-Ph f-Bu 5-F-3-CF3-Ph 3-Br-Ph Ph 3-I-Ph Compounds of Formula E9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Me-Ph 3,5-diF-Ph 3-F-4-Cl-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diC!-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-CI-Ph 3-Me-Ph 3-CF3-Ph 3-CI-2-Me-Ph 3-r-Bu-Ph TABLE 6 defined as: R9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-Me0-Ph 5-F-2-lhienyI 5-Br-2-thieny! 5-Cl-2-ihienyl 2,5-diF-3-thienyl 2,5-diCl-3-thienyl 2,5-diBr-3-thieny! 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Mc-4-Cl-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-r-Bu-Ph (2-CN-Ph )CH2 4-I-PIi E9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrim.idinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-thienyl 3-0CF2H-Ph 4-0CF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-f-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinvl 4-CF3-2-pyridinvl 4-CF3-2-pyrimidinyl WO 97/00612 FCT/US96/10326 85 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-/-Bu-2-pyridinyl 2-Br-5-pyridinyl 3-Cl-benzyi 4-Me3Si-2-pyridinyl 4,5-diBr-2-thienyl 2-CI-benzyl 4-Me3Ge-2-pyridinyl 4,5-diCl-2-thienyl 2-CN-benzyI 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-CsC)-Ph 5-CF3-2-furanyI 3,4,5-lriCl-2-thi2nyl 4-(Me3Si-CsC)-Ph 5-CF3-2-thienyl 3-(OCH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(CsCH)-Ph 3-0S02CF3-Ph 4-I-Ph 2-CF3CH20-5-pyridiny] 4-0S02CF3-Ph 3-C02Me-Ph 4-CI-benzyl 4-EtO-2-pyrimidiny! 3-C02-f-Bu-Ph 2-Et-Ph 4,6-diMe0-2-pyrimidinyl 3-C02Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl TABLE 7 Compounds of Formula IA defined as: N-n —R9 MeO^ 0-Nx Me R9 R9 R9 R9 2-Br-Ph 2-Me-Ph 2-Et-Ph 4-Et0-2-pyrimidinyl 2-CN-Ph 2-F-Ph 2-Cl-Ph 4,6-diMe0-2-pyrimidinyl 2,4-diCI-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 WO 97/00612 PCT/US96/10326 86 4-Me-Ph 3-CF30-Ph 6-Me0-4-pyrimidinyl 3-MeO-2-pyridinyl 4-CI-Ph 4-Br-Ph 5-Me-2-furanyl 5-CN-2-pyrid!nyl 3-Me-Ph 3-El-Ph 2,5-diMe-3-thienyl 6-Me-2-pyridinyl 3-CF3-Ph 4-MeO-Ph 3-0CF2H-Ph 3,5-diBr-Ph 3-Cl-2-Me-Ph 4-f-Bu-Ph 4-OCF2H-Ph 4-/-Bu-2-pyridinyl 3-r-Bu-Ph 4-CN-Ph 3-Me3Si-Ph 4-Me-^Si-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-diCi-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 3-3r-Ph 3-I-Ph 4-I-Ph f-Bu Compounds of Formula IA defined as: MeO. O—N TABLE 8 M' o o N V R9 Me R9 R9 E9 R9 2-Br-Ph 2-Me-Ph 2-Et-Ph 4-Et0-2-pyrimidinyl 2-CN-Ph 2-F-Ph 2-Cl-Ph 4,6-diMeO-2-pyrimidinyi 2,4-diCl-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-pyridinvl 4-N02-Ph 2-MeO-Ph 4-MeO-2-pyrimidinyl 4-CF3-2-pyrimidinyl 4-CF30-Ph 2,6-diMeO-Ph 4-Me-2-pyrimidinyI 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-pvridinyl 3-Me-Ph 3-Et-Ph 2,5-diMe-3-thienvl 6-Me-2-pyridinyl 3-CF3-Ph 4-MeO-Ph 3-0CF2H-?h 3,5-diBr-Ph 3-CI-2-Me-Ph 4-r-Bu-Ph 4-0CF->H-Ph 4-/-Bu-2-pyridinyl WO 97/00612 PCT/US96/10326 87 3-:-Bu-Ph 4-CN-Ph 3-Me3Si-Ph 3-F-Ph 4-N02-Ph 4-Me3Si-Ph 4-CF3-Ph 3,4-diMe-Ph 3-Me3Ge-Ph 3,4-diCl-Ph 3,5-diMe-Ph 4-Me3Ge-Ph 3,4-diCF3-Ph 4-F-3-CF3-Ph 3-EtO-Ph 4-F-Ph 5-F-3-CF3-Ph Ph 3-Cl-Ph 3-Br-Ph 3-I-Ph r-Bu 4-Me3Si-2-pyridinvl 4-Me-jGe-2-pyridinyl 4,6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl (2-CN-Ph)CH2 4-I-Ph N—N \ Me R9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Me-Ph 3,5-diF-Ph 3-F-4-Cl-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diCl-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph R9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-ihienyl 5-Br-2-thienyl 5-Cl-2-thienyl 2,5-diF-3-thienyl 2,5-diCl-3-thienyl 2,5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Me-4-Cl-Ph 3,5-diCl-Ph 3,5-diCF_rPh 2-MeO-Ph R9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-thienyl 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph WO 97/00612 PCT/US96/10326 4-Me-Ph 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-Cl-2-Me-Ph 3-/-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCl-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thienyl 4,5-diCl-2-thienyl 4,5-diF-2-thienyl 3,4,5-triCl-2-thienyl 3-(C=CH)-Ph 4-(C=CH)-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph 88 2,6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-r-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzyl 2-CN-benzyl 3-(Me3Si-C=C)-Ph 4-(Me3Si-OC)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidiny!. 4.6-diMeO-2-pyrirr.idinyl 4,6-diMe-2-pyrimidinyl 4-C02Me-Ph 4-C02-r-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-MeO-2-pyridinyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-r-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-r-Bu-Ph 3-C02Et-Ph WO 97/00612 PCT/US96/10326 89 TABLE 10 Compounds of Formula IA defined as: N—N \ Me R10a = Hand 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-CI-Ph 5-Br-2-thieny] 4-M e-2-pyrimi di ny 1 3-MeO-Ph 5-CI-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-lhienyl 3-Br-Ph 2,5-diBr-3-thienyI 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-Ci-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-C02Me-Ph 4-Cl-Ph 3-CF30-Ph 4-C02-r-Bu-Ph 3-Me-Ph 4-Br-Ph 4-C02Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-/-Bu-Ph 4-r-Bu-Ph 4-CF3-2-pyrimidinyl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinyl WO 97/00612 PCT/US96/10326 90 4-CF3-Ph 4-N02-Ph 3-MeO-2-pyridinyl 3,4-diCI-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-r-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-pyridiny! 4,5-diCl-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrirnidinyl 4,5-diF-2-thienyl 3-(Me3Si-C=C)-Ph 5-CF3-2-furanyl 3,4,5-triCl-2-thienyl 4-(Me3Si-OC)-Ph 5-CF3-2-thienyl 3-(C=CH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(CsCH)-Ph 3-0S02CF3-Ph 4-I-Ph 2-CF3CH20-5-pyridinyl 4-0S02CF3-Ph 3-C02Me-Ph 4-Cl-benzyl 4-EtO-2-pyrimidinyl 3-C02-r-Bu-Ph 2-Et-Ph 4,6-diMcO-2-pyrimidinyl 3-CO^)Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl RlOa _ arnj E9 E9 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-C!-4-Me-Ph 3-Br-4-Me0-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-thienyI 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thienyl 3-OCF2H-Ph 2-Br-Ph 4-SCFoH-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-COoMe-Ph WO 97/00612 PCTAJS96/10326 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-Cl-2-Me-Ph 3-r-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thienyl 4,5-diCl-2-thienyl 4,5-diF-2-thienyl 3,4,5-triCl-2-thienyl 3-(C=CH)-Ph 4-(OCH)-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph R10a = Br and R9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Me-Ph 3,5-diF-Ph 3-F-4-Cl-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 91 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-f-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzyl 2-CN-benzyI 3-(Me3Si-CsC)-Ph 4-(Me3Si-CsC)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-Et0-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidiny] R9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 5-Br-2-thienyl 5-C!-2-thienyl 2.5-diF-3-thienyl 2,5-diCl-3-thienyl 2,5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 4-C02-r-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinvl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-MeO-2-pyridinyl 5-CN-2-pyridiny! 6-Me-2-pyridinyl 3.5-diBr-Ph 4-r-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-r-Bu-Ph 3-C02Et-Ph E9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-Me0-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-thienvl 3-0CF2H-Ph 4-0CF2H-Ph 3-Me3Si-Ph WO 97/00612 PCT/US96/10326 2,4-diCl-Pli 2-CF3-Ph 2-I-Ph 4-NOi-Ph 4-CF30-Ph 4-Me-Ph 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-Cl-2-Me-Ph 3-f-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thienyl 4,5-diCl-2-thienyI 4,5-diF-2-chienyl 3,4,5-triCI-2-thienyl 3-(CsCH)-Ph 4-(C=CH)-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph R10a = Cl and R9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Me-Ph 3,5-diF-Ph 3-F-4-CI-Ph 92 2-F-Ph 2-Me-4-C!-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-?-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzy! 2-Cl-benzyl 2-CN-benzyl 3-(Me3Si-OC)-Ph 4-(Me3Si-OC)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidinyl B9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 5-Br-2-ihienyl 4-Me3Si-Ph 3-Me-^Ge-Ph 4-Me-?Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-r-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-MeO-2-pyridinyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-f-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3 Ge-2-py ridinyl 4.6-diCF3-2-pyrirmdinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-r-Bu-Ph 3-COoEt-Ph R9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimid:nyl WO 97/00612 PCT/US96/10326 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diCl-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-Cl-2-Me-Ph 3-i-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thienyl 4,5-diCl-2-thienyl 4,5-diF-2-thienyl 3,4,5-triCl-2-thienyI 3-(CsCH)-Ph 4-(C=CH)-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph 93 5-CI-2-thienyI 2,5-diF-3-thienyl 2,5-diCl-3-thienyl 2,5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Me-4-CI-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-r-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzyl 2-CN-benzyl 3-(Me3Si-CHC)-Ph 4-(Me3Si-CsC)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidinyl 6-MeO-4-pyrimidiny! 5-Me-2-furanyl 2,5-diMe-3-thienyl 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-r-Bu-Ph 4-C02El-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-MeO-2-pyridiriyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-r-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-py;'.^lidinyl 5-CF3*2-furanyl 5-CF3-2-thienyl 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-r-Bu-Ph 3-C02Et-Ph WO 97/00612 PCT/US96/10326 Rl0a = CN and B9 R9 R9 3,4-diF-Ph 4-Ph-Ph 6-CF3-2-pyridiny! 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-Me0-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-thienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-CI-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 3-0CF2H-Ph 2-Br-Ph 4-SCFoH-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-diCI-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-COoMe-Ph 4-Cl-Ph 3-CF30-Ph 4-C02-r-Bu-Ph 3-Me-Ph 4-Br-Ph 4-C02Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pvridinyl 3-r-Bu-Ph 4-;-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-diCI-Ph 3,4-diMe-Ph 5-CN-2-pyridinyl 3.4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pyridinyI 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-/-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-pvridinyl 4,5-diCI-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-OC)-Ph 5-CF3-2-furanyl 3.4,5-triCl-2-thienyl 4-(Me3Si-CsC)-Ph 5-CF3-2-thienyl WO 97/00612 PCT/US96/10326 3-(CsCH)-Ph 4-(CsCH1-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph 95 3.5-diCF3-benzvl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidinyl 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-/-Bu-Ph 3-C02Et-Ph R10a = Fand R9 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3.5-diF-Ph 3,5-diCl-Ph 3.5-diCF3-Ph C(CH3)3 RlOa = n-butvl and r? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 RIOa = 1 and r? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph ?.,5-diCF3-Ph C(CH3)3 plOa /grf-butvi and r? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 rIOu _ fj-propyi and e2 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 R10a = CF3 and R? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 RlOa _ isonropyi and R9 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 R10a = MeO and R? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 WO 97/00612 FCT/US96/10326 96 TABLE 11 Compounds of Formula IA defined as: N—N \ Me 3,4-diF-Pb 4-Ph-Ph 3,5-diBr-4-MeO-Ph 4-Br-3-Me-Ph 3-CI-4-Me-Ph 3-Br-4-MeO-Ph 3,5-diF-Ph 5-F-2-thienyI 3-F-4-Cl-Ph 5-Br-2-thienyl 3-MeO-Ph 5-Cl-2-thienyl 3-Cl-Ph 2,5-diF-3-thienyl C(CH3)3 2,5-diCl-3-lhienyl 3-Br-Ph 2,5-diBr-3-thienyl 2-Br-Ph 4-SCF2H-Ph 2-CN-Ph 2-Me-Ph 2,4-diCl-Ph 2-F-Ph 2-CF3-Pn 2-Me-4-Cl-Ph 2-I-Ph 3,5-diCl-Ph 4-N02-Ph 3,5-diCF3-Ph 4-CF30-Ph 2-MeO-Ph 4-Me-Ph 2,6-diMeO-Ph 4-CI-Ph 3-CF30-Ph 3-Me-Ph 4-Br-Ph 3-CF3-Ph 3-Et-Ph 3-Cl-2-Me-Ph 4-MeO-Ph 3-r-Bu-Ph 4-/-Bu-Ph 3-F-Ph 4-CN-Ph 4-CF3-Ph 4-N02-Ph 3,4-diCI-Ph 3,4-diMe-Ph 3.4-diCF3-Ph 3,5-diMe-Ph E9 6-CF3*2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-thienyI 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-/-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidin>i 5-CF3-3-pyridinyl 3-MeO-2-pyridinyl 5-CN-2-pyridirsyl 6-Me-2-pyridinyl WO 97/00612 PCT/US96/10326 4-F-Fh 3-I-Ph 2-Br-5-pyridinyl 4,5-diBr-2-thienyl 4,5-diCl-2-thienyl 4,5-diF-2-thienyl 3,4,5-triCl-2-thienyl 3-(C=CH)-Ph 4-(CsCH)-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph 97 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzyl 2-CN-benzyl 3-(Me3Si-CsC)-Ph 4-(Me3Si-C=C)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidinyl 3.5-diBr-Ph 4-i-Bu-2-pyridinyl 4-Me^Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-/-Bu-Ph 3-C02Et-Ph TABLE 12 Compounds of Formula IA defined as: R9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Me-Ph 3,5-diF-Ph 3-F-4-Cl-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diCl-Ph N—N \ Me R9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 5-Br-2-thienyl 5-Cl-2-thienyl 2,5-diF-3-thienyl 2,5-d:Cl-3-thienyl 2,5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 2-F-Ph R9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyI 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-thienyl 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph WO 97/00612 PCT/US96/10326 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-CI-2-Me-Ph 3-r-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-ihienyl 4,5-diCI-2-thienyi 4,5-diF-2-thienyl 3,4,5-triCI-2-thienyI 3-(OCH)-Ph 4-(C=CH)-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph 98 2-Me-4-Cl-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-El-Ph 4-MeO-Ph 4-/-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzyl 2-CN-benzyl 3-(Me3Si-CsC)-Ph 4-(Me3Si-CsC)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph H-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidi nyl 4.6-diMe-2-pyrimidinyI 3-Me3Ge-Ph 4-Me3Ge-Pli Ph 3-CN-Ph 4-C02Me-Ph 4-CD2-/-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-MeO-2-pyridinyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-r-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-f-Bu-Ph 3-C02Et-Ph WO 97/00612 PCT/TJS96/10326 TABLE 13 Compounds of Formula IA defined as: rlftl N—N \ Me R10a = Hand R9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Me-Ph 3,5-diF-Ph 3-F-4-CI-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diCl-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-C!-Ph 3-Me-Ph 3-CF3-Ph 3-CI-2-Me-Ph 3-r-Bu-Ph 3-F-Ph R9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 5-Br-2-thienyl 5-Cl-2-thienyl 2,5-diF-3-thienyl 2,5-diCl-3-thienyl 2,5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Me-4-C)-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-El-Ph 4-MeO-Ph 4-r-Bu-Ph 4-CN-Ph R9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-MeO-4-pyrimidi nyl 5-Me-2-furanyl 2,5-diMe-3-thienyl 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-r-Bu-Ph 4-C02Et-Ph 6-CF3-4-pvrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl WO 97/00612 PCT/US96/10326 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thicnyl 4,5-diCl-2-thir.nyl 4,5-diF-2-ihienyl 3,4,5-triC!-2-thienyi 3-(C=CH)-Ph 4-(CsCH)-Ph 2-CF3CH20-5-pyridiny 1 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph RlOa _ an(j R9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Mt;-Ph 3,5-diF-Ph 3-F-4-Cl-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diCl-Ph 2-CF3-Pn 2-I-Ph 4-NG2-Ph 4-CF30-Ph 100 4-N02-Ph 3.4-diMe-Ph 3.5-diM.e-Ph 4-F-3-CFvPh 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzyl 2-CN-benzyl 3-(Me3Si-CsC)-Ph 4-(Me3Si-OC)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidinyl E9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 5-Br-2-thienyl 5-Cl-2-thienyl 2,5-diF-3-thienyl 2,5-diCl-3-thienyl 2,5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Me-4-Cl-Ph 3.5-diCl-Ph 3,5-diCF3-Ph 2-MeO-Ph 3-MeO-2-pyridinyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-;-Bu-2-pyridinyl 4-Me^Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5CF3-2-thieny! 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-/-Bu-Ph 3-C02Et-Ph R9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-thienyl 3-OCFoH-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph WO 97/00612 PCT/US96/10326 4-Me-Ph 4-C'l-Ph 3-Me-Ph 3-CF3-Ph 3-CI-2-Me-Ph 3-r-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-p>Tidinyl 4.5-aiBr-2-thienyl 4,5-diCl-2-thienyl 4,5-diF-2-thienyl 3,4,5-triCl-2-thienyl 3-(OCH)-Ph 4-(OCH)-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph R10a = Brand R9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Me-Ph 3,5-diF-Ph 3-F-4-Cl-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 101 2,6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-/-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzyl 2-CN-benzyl 3-(Me3Si-OC)-Ph 4-(Me3Si-C=C)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidinyl R9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 5-Br-2-thienyl 5-CI-2-thieny! 2,5-diF-3-thienyl 2,5-diCI-3-thienyl 2,5-diBr-3-thienyl 4-SCFoH-Ph 4-C02Me-Ph 4-C02-r-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinyl 4-CF-^-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-MeO-2-pyridinyl 5-CN-2-pyridiny! 6-Me-2-pvridiny! 3.5-diBr-Ph 4-f-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtC-Ph 4-I-Ph 3-C02Me-Ph 3-C02-f-Bu-Ph 3-C02Et-Ph E9 6-CF^-2-pyridinyl 2-pyrimidinyl 4 pyrimidinyl 4-MeO-2-pyrimidinyI 4-Me-2-pyrimidinyl 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-thienyl 3-OCF2H-Ph 4-0CF-,H-Ph WO 97/00612 PCT/XJS96/10326 2-CN-Ph 2,4-diCl-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-Cl-2-Me-Ph 3-r-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thienyl 4,5-diCl-2-thienyl 4,5-diF-2-thienyl 3,4,5-triCl-2-thienyl 3-(CsCH)-Ph 4-(OCH)-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph R10a = Cl and R9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Me-Ph 3.5-diF-Ph 102 2-Me-Ph 2-F-Ph 2-Me-4-Cl-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Fn 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph J-f-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzyl 2-CN-benzvl 3-(Me3Si-OC)-Ph 4-(Me3Si-C=C)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidinyl R9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 3-Me3Si-I-h 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-:-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyriTnidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-MeO-2-pyridinyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3,5-diBr-Ph 4-r-Bu-2-pyridinyl 4-Me3Si-2-pyridiny] 4-Me3Ge-2-pyridinyl 4,6"diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyi 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-r-Bu-Ph 3-C02Et-Ph R9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl WO 97/00612 PCT/US96/10326 3-F-4-CI-Ph 3-MeU-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diCl-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-CI-Ph 3-Me-Ph 3-CF3-Ph 3-Cl-2-Me-Ph 3-r-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thienyl 4,5-diCl-2-thienyl 4,5-diF-2-thienyl 3,4,5-lriCI-2-thienyl 3-(CsCH)-Ph 4-(C=CH)-Ph 2-CF3CH20-5-pyridinyl 4-CI-berizyl 2-Et-Ph 2-Cl-Ph 103 5-Br-2-thienyl 5-C1 -2-thieny 1 2,5-diF-3-thieryl 2,5-diCl-3-thienyI 2.5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Me-4-Cl-Ph 3.5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-r-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzyl 2-CN-benzyl 3-(Me3Si-OC)-Ph 4-(Me3Si-CsC)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinvl 4.6-diMe-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-thicnvl 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Mc3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-/-Bu-Ph 4-COoEt-Ph 6-CF3-4-py ri midi nvl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-MeO-2-pyridiny) 5-CN-2-pyridir>yl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-r-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-/-Bu-Ph 3-COoEt-Ph WO 97/00612 R1()a = CN and £9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-CI-4-Me-Ph 3,5-diF-Ph 3-F-4-Cl-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diCl-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-CI-2-Me-Ph 3-r-Bu-Ph 3-F Tn 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-i-Ph 2-Br-5-pyridinyI 4.5-diBr-2-thienyl 4,5-diCl-2-thienyI 4,5-diF-2-thienyl 3,4,5-triCl-2-thienyl 3-(CsCH)-Ph 104 R9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 5-Br-2-ihienyl 5-Cl-2-thienyl 2,5-diF-3-ihienyl 2,5-diCI-3-thienyl 2,5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Me-4-Cl-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-r-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzyI 2-CN-benzyl 3-(Me3Si-CsC)-Ph 4-fMe3Si-C=C)-Ph 3,5-diCF3-benzyl PCT/US96/10326 R9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-MeO-4-pvrimidinyl 5-Me-2-furanyl 2,5-diMe-3-ihienyl 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me^Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-r-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinyI 4-CF3-2-p_vridinyl 4-CF3-2-pyrimidinyI 5-CF3-3-pyridinyl 3-MeO-2-pyridinyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-/-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3Ge-2-pyridinvl 4.6-diCF^-2-pyrimidinyl 5-CF3-2-furany! 5-CF3-2-ihienyl 3-EtO-Ph WO 97/00612 PCT/US96/10326 105 4-(L'sCH)-Ph 2-CF3CH20-5-pvridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph RlOa _ p an(j R9 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 RlOa = n-butvl and r£ 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4,6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidinyl 4-I-Ph 3-C02\le-Ph 3-C02-r-Bu-Ph 3-COnEt-Ph >10a _ = I and R? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 R10a = rert-butvl and R? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 rIQs = n-propvl and R? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 R10a = CF3 and R? 3-CF3-Ph 3-CF30-Ph 3-OCFoH-Ph 4* 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 r 1 Oa _ iS0pr0DVi and r2 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3.5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 R10a = MeO and e£ 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 WO 97/00612 PCT/US96/10326 106 TABLE 14 Compounds of Formula IA defined as: RlO! CH- Me R9 N V v\ N—N \ Me R10a = Hand R9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Me-Ph 3,5-diF-Ph 3-F-4-Cl-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diCl-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-C]-2-Me-Ph 3-f-Bu-Ph 3-F-Ph R9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 5-Br-2-thienyl 5-Cl-2-thienyl 2,5-diF-3-thienyI 2,5-diCl-3-thienyl 2,5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Me-4-Cl-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-/-Bu-Ph 4-CN-Ph R9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-thienyl 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-COi-r-Bu-Ph 4-COoEt-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl WO 97/00612 PCT/US96/10326 J-CFyPh 3.4-diCI-Ph 3.4-diCFvPh 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thienyl 4,5-diC!-2-thienyl 4.5-diF-2-thienyl 3,4,5-triCI-2-thienyl 3-(C=CH)-Ph 4-(OCH)-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph RlOa _ j^e ancj E9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-CM-Me-Ph 3,5-diF-Ph 3-F-4-Cl-Ph 3-MeO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2.4-diCl-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 107 4-N03-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-Cl-benzy! 2-CN-benzyl 3-(Me3Si-C=C)-Ph 4-(Me3Si-CsC)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidinyl E9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 5-Br-2-thienyl 5-Cl-2-thienyl 2,5-diF-3-thienyl 2,5-diCl-3-thienyl 2,5-diBr-3-thieny! 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Me-4-Cl-Ph 3,5-diCl-Ph 3,5-diCF3-Ph 2-MeO-Ph 3-MeO-2-pvridinyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-/-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtO-Ph 4-1-Ph 3-C02Me-Ph 3-C02*f-Bu-Ph 3-C02Et-P!i E9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pyrimidinyl 4-Me-2-pyrimidinyl 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2,5-diMe-3-thienyl 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph WO 97/00612 PCT/US96/10326 108 4-Me-Ph 2,6-diMeO-Ph 4-COnMe-Ph 4-Cl-Ph 3-CF30-Ph 4-COt-r-Bu-Ph 3-Me-Ph 4-Br-Ph 4-C02Et-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-CI-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyI 3-r-Bu-Ph 4-/-Bu-Ph 4-CF3-2-pyrimidinvl 3-F-Ph 4-CN-Ph 5-CF3-3-pyridinvl 4-CF3-Ph 4-N02-Ph 3-MeO-2-pyridinyl 3,4-diCI-Ph 3,4-diMe-Ph 5-CN-2-pvridinyl 3,4-diCF3-Ph 3,5-diMe-Ph 6-Me-2-pvridinyl 4-F-Ph 4-F-3-CF3-Ph 3,5-diBr-Ph 3-I-Ph 5-F-3-CF3-Ph 4-r-Bu-2-pyridiny! 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-diCI-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-lhienyl 3-(Me3Si-OC)-Ph 5-CF3-2-furanyl 3,4.5-triCl-2-thienyl 4-(Me3Si-CsC)-Ph 5-CF3-2-thienyl 3-(CsCH)-Ph 3,5-diCF3-benzyl 3-EtO-Ph 4-(C=CH)-Ph 3-0S02CF3-Ph 4-I-Ph 2-CF3CH20-5-pyridinyl 4-0S02CF3-Ph 3-C02Me-Ph 4-CI-benzyl 4-EtO-2-pyrimidi.iyl 3-C02-/-Bu-Ph 2-Et-Ph 4,6-diMcO-2-pyrimidinyl 3-C02Et-Ph 2-Cl-Ph 4,6-diMe-2-pyrimidinyl R10a = Br and S9 R9 E9 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-thienyI 4-MeO-2-pvrimidinyl 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-ihienyI 5-Me-2-furanyl CfCH3)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-SCFoH-Ph 4-OCFoH-Ph WO 97/00612 PCT/US96/10326 2-CN-Ph 2,4-diCl-Ph 2-CF?-Ph 2-I-Ph 4-NOo-Ph 4-CF30-Ph 4-Me-Ph 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-Cl-2-Me-Ph 3-r-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thienyI 4,5-diCl-2-thienyl 4,5-diF-2-thienyl 3,4,5-triCl-2-thienyl 3-(CsCH)-Ph 4-(OCH)-Ph 2-CF3CH20-5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph R10a =. CI and s9 3.4-diF-Ph 3.5-diBr-4-MeO-Ph 3-Cl-4-Me-Ph 3.5-diF-Ph J 09 2-Me-Ph 2-F-Ph 2-Me-4-CI-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-f-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-C!-benzyl 2-CN-benzyl 3-(Me3Si-CsC)-Ph 4-(Me3Si-CsC)-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyrimidinyl R9 4-Ph-Ph 4-Br-3-Me-Ph 3-Br-4-MeO-Ph 5-F-2-thienyl 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-f-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-MeO-2-pyridinyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-r-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-r-Bu-Ph 3-C02Et-Ph R9 6-CF3-2-pyridinyl 2-pyrimidinyl 4-pyrimidinyl 4-MeO-2-pvrimidinyl WO 97/00612 PCTAJS96/10326 3-F-4-CI-Ph 3-McO-Ph 3-Cl-Ph C(CH3)3 3-Br-Ph 2-Br-Ph 2-CN-Ph 2,4-diCl-Ph 2-CF3-Ph 2-I-Ph 4-N02-Ph 4-CF30-Ph 4-Me-Ph 4-Cl-Ph 3-Me-Ph 3-CF3-Ph 3-Cl-2-Me-Ph 3-r-Bu-Ph 3-F-Ph 4-CF3-Ph 3,4-diCI-Ph 3.4-diCF3-Ph 4-F-Ph 3-I-Ph 2-Br-5-pyridinyl 4.5-diBr-2-thienyl 4,5-diCI-2-thienyl 4,5-diF-2-thienyl 3,4,5-triCI-2-thienyl 3-(CsCH)-Ph 4-(CsCHH;' 2-CF3CHj>.: 5-pyridinyl 4-Cl-benzyl 2-Et-Ph 2-.Cl-Ph 110 5-Br-2-thienyl 5-CI-2-thienyl 2,5-diF-3-thienyl 2,5-diCI-3-thienyl 2,5-diBr-3-thienyl 4-SCF2H-Ph 2-Me-Ph 2-F-Ph 2-Me-4-Cl-Ph 3,5-diCl-Ph 3.5-diCF3-Ph 2-MeO-Ph 2.6-diMeO-Ph 3-CF30-Ph 4-Br-Ph 3-Et-Ph 4-MeO-Ph 4-;-Bu-Ph 4-CN-Ph 4-N02-Ph 3.4-diMe-Ph 3.5-diMe-Ph 4-F-3-CF3-Ph 5-F-3-CF3-Ph 3-Cl-benzyl 2-CI-benzyl 2-CN-benzyl 3-(Me3Si-C2C)-Ph 4-(Me3Si-CHC)-Ph 3.5-diCF3-benzyl 3-0S07CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMe-2-pyriinidinyl 4-Mo-2-pyrimidinyl 6-MeO-4-pyrimidinyl 5-Me-2-furanyl 2.5-diMe-3-ihienyl 3-OCF2H-Ph 4-OCF2H-Ph 3-Me3Si-Ph 4-Me3Si-Ph 3-Me3Ge-Ph 4-Me3Ge-Ph Ph 3-CN-Ph 4-C02Me-Ph 4-C02-r-Bu-Ph 4-C02Et-Ph 6-CF3-4-pyrimidinyl 4-CF3-2-pyridinyl 4-CF3-2-pyrimidinyl 5-CF3-3-pyridinyl 3-McO-2-pyridinyl 5-CN-2-pyridinyl 6-Me-2-pyridinyl 3.5-diBr-Ph 4-r-Bu-2-pyridinyl 4-Me3Si-2-pyridinyl 4-Me3Ge-2-pyridinyl 4.6-diCF3-2-pyrimidinyl 5-CF3-2-furanyl 5-CF3-2-thienyl 3-EtC-Ph 4-I-Ph 3-COoMe-Ph 3-C02-/-Bu-Ph 3-C02Et-Ph WO 97/00612 FCT/US96/10326 rIOu _ cn anc| 111 R9 E9 E9 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-CI-4-Me-Ph 3-Br-4-MeO-Ph 4-pyrimidinyl 3,5-diF-Ph 5-F-2-thienvl 4-MeO-2-pyrimidinyl 3-F-4-Cl-Ph 5-Br-2-ihienyl 4-Me-2-pyrimidinyl 3-MeO-Ph 5-Cl-2-thienyl 6-MeO-4-pyrimidinyl 3-Cl-Ph 2,5-diF-3-thien\i 5-Me-2-furanyl C(CH3)3 2,5-diCl-3-thienyl 2,5-diMe-3-thienyl 3-Br-Ph 2,5-diBr-3-thiexiyl 3-OCF2H-Ph 2-Br-Ph 4-SCFoH-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-C02Me-Ph 4-Cl-Ph 3-CF30-Ph 4-C02-r-Bu-Ph 3-Me-Ph 4-Br-Ph 4-COoEt-Ph 3-CF3-Ph 3-Et-Ph 6-CF3-4-pyrimidinyl 3-Cl-2-Me-Ph 4-MeO-Ph 4-CF3-2-pyridinyl 3-r-Bu-Ph 4-r-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-diCI-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-r-Bu-2-pyridinyl 2-Br-5-pyridiny; 3-Cl-benzyl 4-Me3Si-2-pyridinyl 4,5-diBr-2-ihienyl 2-CI-benzyI 4-Me3Ge-2-pyridinyl 4,5-diCI-2-thienyl 2-CN-benzyl 4,6-diCF3-2-pyrimidinyl 4,5-diF-2-thienyl 3-(Me3Si-C=C)-Fh 5-CF3-2-furanyl 3,4,5-triCI-2-thienyl 4-(Me3Si-C=C)-Ph 5-CF3-2-thienyl WO 97/00612 PCT/US96/10326 112 3-(ChCH)-PII 4-(C=CH)-Ph 2-CF3CH20-5-pvridiny! 4-Cl-benzyl 2-Et-Ph 2-Cl-Ph 3.5-diCF3-benzyl 3-0S02CF3-Ph 4-0S02CF3-Ph 4-EtO-2-pyrimidinyl 4.6-diMeO-2-pyrimidinyl 4,6-diMc-2-pyrimidinyl 3-EtO-Ph 4-I-Ph 3-C02Me-Ph 3-C02-'-Bu-Ph 3-COnEt-Ph R10a=:Fand E? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-?h 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 RlOa _ butyl and s2 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 R10a = I and R? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3.5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 RlOa _ ffrj.bu(vi and R? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 RlOa _ n.Dr0pV| an(j R? 3-CF3-Ph 3-CF30-Ph 3-OCF2Ii-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 R10a = CF3 and R? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 RlOa_ isopropy] and R? 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3,5-diCF3-Ph C(CH3)3 >10a _ = MeO and r£ 3-CF3-Ph 3-CF30-Ph 3-OCF2H-Ph 3,5-diF-Ph 3,5-diCl-Ph 3.5-diCF3-Ph C(CH3)3 Formulation/Utility 5 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. 10 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 WO 97/00612 PCT/US96/10326 13 10 15 20 25 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)encapsulatcd 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 IniTedient Diluent Surfactant Water-Dispersible and Water-soluble Granules, Tablets and Powders. 5-90 0-94 1-15 Suspensions, Emulsions, Solutions (including Emulsifiable Concentrates) 5-50 40-95 0-15 Dusts Granules and Pellets 1-25 0.01-99 70-99 5-99.99 0-5 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 Puh\ 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, A^M-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 WO 97/00612 PCT/US96/10326 1 14 bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, M/V dimethylformamide, dimethyl sulfoxide, /V-alkylpyrrolidone, ethylene glvco1, polypropylene glycol, paraffins, alkylbenzenes. alkylnaphthalenes. oils of olive, castor, linseed, tuny, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty 5 acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hvdroxy-4-methvl-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 10 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 15 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. Water-dispersibJe 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. 20 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., 25 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. 30 Example A Wettable Powder 35 Compound 345 dodecylphenol polyethylene glycol ether sodium ligninsuifonate sodium silicoaluminate montmorillonite (calcined) 65.0% 2.07c 4.07c 6.0 7c 23.0 9c. WO 97/00612 PCT/US96/10326 115 Example B Granule Compound 515 10.0% attapulgite granules (low volatile mutter, 5 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.07c. Example C Extruded Pellet Compound 680 25.0% anhydrous sodium sulfate 10.0% 10 crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonaie 1.0% calcium/magnesium bentonite 59.0%. Example D Emulsifiable Concentrate 15 Compound 699 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%. The compounds of Lhis invention are useful as plant disease control agents. The 20 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 25 broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and Deuteromycete classes. They are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal, and fruit crops. These pathogens include Plasmopara viticola, Phytophthora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, 30 Alternaria brcissicae, Septoria nodorum, Septoria tritici, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Pyricularia o;yzae, Podosphaera leucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recond'u.., Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Puccinia arachidis, 35 Rhizoctonia solani, Sphaerotheca fuliginea, Fusarium oxysporum, Venicillium dahliae, Pythium aphanidertnatum, Phytophthora megasperma, Sclerotinia sclcrotiorum. WO 97700612 PCT /US96/10326 1 16 Sclcroiium ralfsii, Erxsiphc polygoni. Pyrcnophora teres, Gciciunannomyces graminis. Rynchosporium secalis, Fusarium roseurn, Brcmici lactucac and other gencrea and species closely related to these pathogens. The compounds of this invention also exhibit activity against a wide spectrum of 5 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 10 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 15 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. 20 Specifically, the compounds are active against southern com rootworm (Diabrotica undecimpunctata howardi), aster leafhopper (Mascrosteles fascifrons), boll weevil (Anthonomus grandis), two-spotted spider mite (Tetranychus urticae), fall armvworm (Spodoptera frugiperda), black bean aphid (Aphis fabae), green peach aphid (Myzus persica), cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis noxia), Eng'ish 25 grain aphid (Sitobion avenae), tobacco budworm (Heliothis virescens), rice water weevil (Lissorhoptrus oryzophilus), rice leaf beetle (Oulema oryzae), whitebacked planthopper (iSogatella 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 30 (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 pacificus, 35 Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi, Panonychus citri, Eotetranychus carpini borealis, Eotetranychus, hicoriae, Eotetranychus sexmaculatus, WO 97/00612 PCT/US96/10326 117 Eoleiranychus yurnensis. Eotetranychus banksi and Oligonychus pratensis\ TenuipaJpidae including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpus ohovatus\ Eriophyidae including Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pvri and Eriophyes mangiferae. See 5 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 10 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. accphate, azinphos-methyl, bifenthrin, buprofe?.in, carbofuran, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, esfenvalerate, fenpropathrin, fenvalerate, fipronil, 15 flucythrinate, tau-fluvalinate, fonophos, imidacloprid, isofenphos, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, oxamvl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, rotenone, sulprofos, tebufenozide, tefluthrin, terbufos, tetrachlorvinphos, thiodicarb, tralomethrin, trichlorfon and 20 triflumuron; fungicides such as azoxystrobin (ICLA5504), benomyl, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), bromuconazole, captafol, captan, carbendazim, chloroneb, chiorothalonil, copper oxychloride, copper salts, cymoxanil, cyproconazole, cyprodinil (CGA 219417), diclomezine, dicloran, difenoconazole, dimethomorph, diniconazole, diniconazoIe-M, dodine, edifenphos, epoxyconazole 25 (BAS 480F), fenarimol, fenbuconazole, fenpiclonil, fenpropidin, fenpropimorph, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl, hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl (BAS 490F), mancozeb, maneb, mepronil, metalaxyl, metconazole, myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl, penconazole, pencvcuron, 30 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; acadcides such as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, fenazaquin, 35 fenbutatin oxide, fenpropathrin, fenpyroximate, hexvthiazox, propargite, pyridaben and WO 97/00612 PCT/US96/10326 lis tebufenpvrad; 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 5 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), 10 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; 15 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 a-td flusilazole; compound 295 and tebuconazole; compound 343 and cyproconazole; compound 343 and cyprodinil (CGA 219417); compound 343 and epoxyconazole 20 (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; 25 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 30 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; 35 compound 538 and cyprodinil (CGA 219417); compound 538 and epoxyconazole (BAS 480F); compound 538 and fenpropidin; compound 538 and fenpropimorph; WO 97/00612 PCT/US96/10326 1 19 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. 5 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. 10 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 from less than 1 g/ha to 5,000 g/ha of active ingredient. Seed and seedlings can normally be protected when seed is treated at a rate of from 0.1 to 10 g per kilogram of seed. 15 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 20 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 25 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 30 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 35 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. WO 97/00612 PCT/US96/10326 120 Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants. other solvents, and synergists such as piperonvl butoxiae often enhance compound efficacy. The rate of application required for effective control will depend on such factors as 5 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 O.OOI kg/hectare may be sufficient or as much as 8 kg hectare 10 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, 15 "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, 20 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, C02Me = methoxycarbonyl, C02Et = ethoxy carbonyl, N02 = nitro, Me3Si = trimethylsilyl, Et3Si = triethylsilyl, MeNH = methylamino, Me2N = dimethylamino, MeS(O) = methylsulfinyl, and 25 MeS02 and S02Me = methylsulfonyl. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared. WO 97/00612 PCT/US96/10326 121 Cmpd No. INDEX TABLE A Structure in. p. (°C) 237 238 732 OCH3 140-142 N—N \ CH-3 OL A CH-J oil" CH3i CF* O N—N \ CH2CH3 oil" 85-88 N—N \ CH2CH3 *See Index Table M for 'H NMR data. 2 3 4 5 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 PCT/US96/10326 122 INDEX TABLE B CH3 Y Z m.p. fC) 0 2-MeO-Ph oil* O CH2-Ph oil* Me oil* CH20 2-Me-Ph oil* CH2ON=C(Me) 3-CF3-Ph 59-61 CH2ON=C(Me) 4-CF3-Ph oil* CH2ON=C(Me) Me 71-73 CH2ON=C(Me) 3-Cl-Ph oil* CH2ON=C(Me) 3-Br-Ph oil* CH2ON=C(Me) 4-Cl-Ph oil* CH2ON=C(Me) 4-Br-Ph oil* CH2ON=C(Me) 4-F-Ph oil* CH2ON=C{Me) 4-MeO-Ph oil* CH2ON=C(Me) 3-CN-Ph oil* CH2ON=C(Me) 4-CN-Ph oil* CH2ON=C(Me) 4-Me-Ph oil* CH2ON=C(Me) 4-Cl-3-Me-Ph oil* CH2ON-C(Me) 3,4-(-0CH20-)-Ph oil* CH2ON=C(Me) 3,4-diMe-Ph oil* CH2ON=C(Me) 3,4-diCI-Ph oil* CH2ON=C(Me) 4-Ph-Ph oil* CH2ON=C(Me) 3-r-Bu-Ph oil* CH2ON=C(Me) 3,5-diCF3-Ph oil* CH2ON=C(Me) 3-MeO-Ph oil* 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 PCT/US96/10326 123 CH2ON=C(Me) 3-Ph-Ph oil* CH2ON=C(Me) 4-PhO-Ph oil* CH2ON=C(Me) 2-pyridinyl oil* CH2ON=C(Me) 3-Me2N-Ph oil* CH2ON=C(Me) 3-CF30-Ph oil* CH2ON=C(Me) 4-(4-MeO-PhO)-Ph oil* CH2ON=C(Me) 4-CF3-2-pyridinyl 94-96 CH2ON=C(Me) 5-Cl-2-thienyl 123-125 CH2ON=C(Me) 4-Me-2-thienyl 130-132 CH2ON=C(Me) 2-thienyl 124-126 CH2ON=C(Me) 3-thienyl 129-131 CH2ON=C(Me) 3-PhO-Ph oil* CH2ON=C(Me) 3-j-PrO-Ph oil* CH2ON=C(Me) 3,5-diCl-Ph oil* CH2ON=C(Et) 3-CF3-Ph oil* CH2ON=C(Me) c-hexyl oil* CH2ON=C(Me) 4-r-Bu-c-hexyl oil* CH2ON=C(Me) 3-(3-CF3-Ph)-Ph oil* CH2ON=C(Me) 3-(3-CF3-PhO)-Ph oil* CH2ON=C(Me) 3-F-5-CF3-Ph oil* CH2ON=C(Me) 3,5-diMe-Ph oil* CH2ON=C(Me) 2-benzofuranyI 101-104 CH2ON=C(Me) 5-Me-2-furanyl oil* CH2ON=C(Me) 4,6-diMe-2-pyridinyl oil* CH2ON=C(Me) 4-c-hexyl-Ph oil* CH2ON=C(Me) 2-quinolinyl 134-136 CH2ON=C(Me) 4-Me-2-Ph-5-pyrimidinyl oil* CH2ON=C(Me) ^ benzo[fc]thiophen-3-yI oil* CH2ON=C(Me) 5-(3-CF3-Ph)-2-thienyl 135-138 CH2ON=C(Me) 3,5-diBr-Ph oil* CH2ON=C(Me) 4-F-3-CF3-Ph oil* CH2ON=C(Me) 2-Cl-6-MeO-4-pyridinyl oil* CH2ON=C(Me) 4,5-diMe-2-thiazolyl 76-78 CH2ON=C(Me) l-Me-3-indoIyl 114-116 CH2ON=C(OMe) 3.5-diC!-Ph oil* CH-iON=C(Me) 3-Et-Ph oil* WO 97/00612 PCT/US96/10326 178 179 180 181 182 183 239 240 CH:ON=C(Me) CH2ON=C(Me) CH2ON=C(Me) CH2ON=C(Me) CH2ON=C(Me) CH2ON=C(Me) 0 OCH-> 124 6-MeO-2-pyrimidinyl 2-naphthalenyl 6-Me-2-naphihalenyl 6-MeO-2-naphihalenyl 6-Br-2-naphthalenyl 5,6,7,8-tetrahydro-2-naphthalenyl 3-[3,5-bis(trifluoromethyl)-phenyl]-l,2.4-thiadiazol-5-yl 4-MeO-Ph oil* oil* oil* oil* oil* oil* 94-97 solid* *See Index Table M for *H NMR data. INDEX TABLE C s \ ch3 Cmpd W X Y 6 0 MeS O Ph 7 O MeO O Me 8 O MeO - Me 9 O MeS - Me 10 O CI - Me 11 O MeO O Ph 12 O CI ch2o 2-Me-Ph 13 O MeO ch2o 2-Me-Ph 14 O EtO ch2o 2-Me-Ph 15 O MeS ch2o 2-Me-Ph 16 O och2c=ch ch2° 2-Me-Ph 17 O CI CH2ON=C(M£) \ 4-Me-Ph 18 O MeO CH2ON=C(Me) \ 4-Me-Ph 19 O MeS CH2ON=C(Me) 4-Me-Ph m.p. (°C) 129-130 123-126 95-97 95-97 99-100 88-91 88-96 110-113 oil* 80-88 122-130 oil* 116-118 oil* WO 97/00612 PCT7US96/10326 125 20 O CI CHoO— oil* o 21 s MeS O Ph oil" 22 0 MeO CH20 126-130 o 23 o CI CH2ON=C(H) Ph oil* 24 o MeS CH20 oil* o 25 0 CI ch2o 3-(PhO)-Ph oil* 26 0 MeO ch2o 3-(PhO)-Ph oil* 27 0 MeO CH2ON=C(H) Ph 101-104 28 0 MeS ch2o 3-(PhO)-Ph 95-100 29 0 ci 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 CI ch2s 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 CI CH2ON=C(Me) 4-Br-Ph gum* 36 0 CI ch20 3-(benzoyl)-Ph oil* 37 0 MeS CH2ON=C(Me) 4-Br-Ph 117-122 38 0 MeO ch2o 3-(benzoyI)-Ph oil* 39 0 CI ch=noch2 4-Cl-Ph oil* 40 0 CI CH2ON=C(Me) l,3-benzodioxol-5-yI oil* 41 0 MeO CH=NOCH2 4-CI-Ph oil* 42 0 MeO CH2ON=C(Me) 1,3-benzodicxol-5-yl oil* 43 6 CI o 6-PhO-4-pyrimidinyl oil* 44 0 MeO CH2S 2-benzothiazolyl 95-97 45 o MeO CH2ON=C(V3e) 2-Me-Ph oil* 46 0 MeO CH2ON=C(Me) 4-CF3-Ph 138-144 47 0 MeO CH2ON=C(CF3) Ph oil* WO 97/00612 PCT/US96/10326 126 48 O MeO CH2ON=C(Me) Ph oil* 49 O MeO CH2ON=C(Me) 3-Me-Ph oil* 50 O MeO CH2ON=C(Me) 4-MeO-Ph oil* 51 O MeO CH:ON=C(Me) 3-Cl-Ph oil* 52 O MeO CH=NOCH(Me) Ph oil* 53 O MeO CH=NOCH2 2-Me-Ph oil* 54 O CI O Ph solid* 55 O CI - ■ CH2Cl:CH2Br(60:40) solid* 56 O MeO - CH2Br solid* 57 O CI O Me 152-154 58 O CI CH2ON=C(Me) 4-CF3-Ph 111-118 59 O MeO CH2ON=C(Me) 3-CF3-Ph 103.5-105.5 60 O MeS CH2ON=C(Me) 4-CF3-Ph oil* 6! O MeO CH2ON=C(CF3) 3-CF3-Ph oil* 62 O MeO O 6-(2-CN-PhO)-4-pyrimidinyl solid/gum* 63 O MeO O 6-Cl-4-pyrimidinyl 133-136 64 O MeO O 6-(2-Me-PhO)-4-pyrimidinyl solid/gum* 65 O MeO O 6-PhO-4-pyrimidinyl gum* 66 O MeO CH2ON=C(Me) 2-pyridinyl 122-124 67 O CI CH2ON=C(Me) 4-pyridinyl 153-155 68 o MeO ch2o 2,5-diMe-Ph 130-135 69 o MeO CH2ON=C(Me) 4-r-Bu-Ph gum* 70 O MeO CH2ON=C(Me) 3,4-diMe-Ph gum* 71 O MeO OCH2 2,5-diMe-Ph 119-122 72 O MeO CH2ON=C(Me) 3,4-diCI-Ph 128-129 73 O MeO CH2ON=C(Me) 3-pyridinyI 90-109 dec. 74 O MeO CH2ON=C(Me) 4-pyridiny! 140-142 75 o ci O 6-Cl-4-pyrimidinyl solid* 76 o MeO CH2ON=C(Me) 4-Ph-Ph about 55* 77 o ci ch20 2,5-diMe-Ph solid* 78 o ci CH2ON-C(Me) 1-Me-3-pyrrolyl 124-131 79 O MeO CH2ON=C(Me) l-Me-3-pyrrolyl 135-137.5 80 O CI CH2ON=C(Me) 2-pyrazinyl 108-111 81 O MeO CH2ON=C(Me) 2-pyrazinvl 119-121 82 O CI CH2ON=C(Me) 3,5-diCF3-Ph oil* 83 O MeO CH2ON=C(Me) 3.5-diCF3-Ph 147-149 WO 97/00612 PCT/US96/10326 127 84 0 MeO CH2ON=C(c-Pr) 4-Cl-Ph oil* 85 0 MeS02 CH2ON=C(Me) 4-CF3-Ph 50-55 86 0 MeS(O) CH:ON=C(Me) 4-CF3-Ph oil/gum" 87 o MeO CH2ON=C(Me) 6-Me-3-pyridinyl 134-136 88 o MeO CH2ON=C(Me) 3-/-Bu-Ph oil* 89 0 MeO CH2ON=C(Me) 3-Ph-Ph oil* 90 o MeO CH2ON=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 CH2ON=C(Me) 3-Me2N-Ph 106-110 94 0 CI CH2ON=C(Me) 3,4-diCI-Ph solid* 95 0 MeO CH2ON=C(Me) 4-CF3-2-pyridinyl 144-145 96 0 MeO CH2ON=C(Me) 3-/i-C4F9-Ph oil* 97 0 MeO CH2ON=C(Me) 4-CN-2-pyridinyl 120-125 98 0 MeO CH2ON=C(Me) 3-PhO-Ph oil* 99 0 MeO CH2ON=C(Et) 3-CF3-Ph oil* 100 0 MeO CH2ON=C(Me) 3-N02-Ph gum* 101 o MeO CH2ON=C(Me) 4-Ph-2-pyridinyl 115-117.5 102 o MeO CH2ON=C(Me) 2-thienyl 100-105 103 0 MeO CH2ON=C(Me) 4-/-Bu-2-pyridinyl 103-105.5 104 0 MeO CH2ON=C(Me) 2-benzofuranyl 149-154 105 o MeO CH2ON=C(Me) 5-Cl-3-Me-benzo[6]thiophen-2- vl 167-169 106 0 MeO CH2ON=C(Me) y 3,5-diCl-Ph 149-153 107 0 MeO CH2ON=C(Me) 2,4-diMe-5-thiazolyl 123-124 108 0 CI CH2ON=C(Me) 2-quinoxalinyl 173-174 109 0 MeO CH2ON=C(Me) 2-quinoxalinyl 225-227 110 0 MeO CH2ON=C(Me) 3,5-diMe-Ph oil* 111 0 CI CH2ON=C(Me) 3-CF3-Ph oil* 112 0 CI CH2ON=C(c-Pr) 4-Cl-Ph gum* 113 0 MeO CH2ON=C(Me) 3-CN-Ph gum* 114 0 CI CH20 5-Me-2-(2-pyridinyl)-4- oil* thiazolyl 115 0 MeO CH2ON=C(Me) 3-F-5-CF3-Ph oil" 116 0 MeO CH2ON=C(CN) 3-CF3-Ph 138-141 WO 97/00612 PCT/IJS96/10326 128 I 17 O MeO CH2ON=C(Me) 6-Me-2-CF3-thiazolo[2,3-c]-l,2,4-triazol-5-yl 157-160 118 O MeO CHiON=C(Me) 3.5-diF-Ph 103-106 119 O MeO CH2ON=C(Me) 3.5-diBr-Ph 139-141 120 O MeO CH2ON=C(Me) 2-quinolinvl 168-171 121 O CI CH2ON=C(Me) 3-CF30-Ph oil* 184 O MeO CH2ON=C(Me) 4-EtO-2-pyrimidinyl 75-78 185 O MeO CH2ON=C(c-Pr) 2-thienyl 137-139 186 O MeO CH2ON=C(Me) 2-Ph-4-thiazolyl 112-113 187 O MeO O 3-[3,5-bis(trifluoromethyl)- 139.5-141.5 Ex. 1 phenyl]-l,2,4-thiadiazol-5-yl 188 O MeO CH2ON=C(Me) 6-Br-2-pyridinyl 151-153 189 O MeO CH2ON=C(OMe) Ph oil* 190 O MeO CH2ON=C(Me) 3-Br-Ph oil* 191 O MeO CH2ON=C(Me) 4-C02Et-2-pyridinyl 133-134 192 O MeO CH=NOCH(Me) 3-CF3-Ph oil* 193 O CI O 3-PhO-Ph oil* 194 O MeO O 3-PhO-Ph oil* 195 0 MeO CH2ON=C(Me) 4-C02Me-2-pyridinyl 150-151.5 196 O MeO CH2ON=C(Me) 5-Me-l-Ph- l//-pyrazol-4-yl 45-49 197 O MeO CH2ON=C(Me) 4-CF3-2-pyrimidinyl 103-105 198 0 MeO CH2ON=C(Me) 3-I-Ph oil* 199 0 MeO CH2ON=C(OMe) 2,6-diCl-4-pyridinyl oil* 200 0 MeO CH2ON=C(OMe) 3-CF3-Ph oil* 201 0 F2CHO direct bond Me solid* 202 0 MeO CH2ON=C(Me) 2-Cl-4-pyrimidinyI 195-200 203 0 C! CH2ON=C(OMe) 2,6-diCI-4-pyridinyI oil* 204 a 0 F2CHO CH2ON=C(Me) 3-CF3-Ph oil* 205 0 CI CH2ON=C(Me) 3,5-diCl-Ph gum* 206 0 MeO CH2ON=C(Me) 2-naphthalenyl 91-94 207 o MeO CH2ON=C(Me) 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl 50* 208 o MeO CH2ON=C(Me) 5,6,7,8-tetrahydro-2-naphthalenyl 106-109 209 o MeO CH2SC(Et)=N 4-Cl-Ph gum* 210b o MeO CH=C(C1)C(=0)0 r-Bu semi-solid* WO 97/00612 PCT/US96/10326 129 211 O MeO CH20N=C(CN)C(=O) 3-CF3-Ph cum* 212 0 MeO CHoON=C(SMe) 3,4-diCI-Ph solid* 213 0 MeO C(=0) Ph 126-134 214 0 MeO CH20N=C(S02Me) 3,4-diCI-Ph semi-solid* 215 0 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 O cf3 direct bond Me 73-77 220 0 cf3 O 3-PhO-Ph oil* 221 s cf3 ch2o 2,5-diMe-Ph gum* 241 o MeO ch2o 2-CN-2-(3-CF3-Ph)ethenyl 115-118 242 o MeO CHIO—N " "T) 136-138 cf3 243 0 MeO CH2o-N=C(CH3)CH2o 3-CF3-Ph oil* 244 0 MeO CH20-N=C(CH3)CH2S l-CH3-ltf-tetrazol-5-yl oil* 245 0 MeO CH20-N=C(CH3) 2,6-diCl-4-pyridinyl 144-146 246 o MeO CH20-N=C(CH3)CH2S 2-benzoxazolyl oil* 247 o MeO CH20-N=C(SCH3) 3,5-diCl-Ph oil* 249 o MeO CH20-N=C(CH3)CH20 3,5-diCl-Ph oil* 250 0 MeO CH2S-C(CH2CH3)=N 3-CF3-Ph oil* 251 0 MeO CH20-N=C(H) 3,5-diCF3-Ph 115-118 252 o MeO CH20-N=C(CH3) 2,6-diCl-4-pyridinyl oil* 253 o MeO CH20-N=C(CH3) 4-(C02-r-B u)-2-pyridinyl 174-175 254 o MeO CH20-N=C(0CH3) 3,5-diCl-Ph oil* 255 0 CI 0 3-MeO-Ph oil* 256 o MeO CH20-N=C(CH3) 2,6-diCl-4-pyritnidinyl 139-140 257 0 MeO CH20-N=C(CH3) 5,6-diCl-3-pyridinyl 130-132 258c 0 MeO CH20-N=C(CH3) 5,6-diCl-3-pyridinyl 112-130 259 0 CI CH20-N=C(CH3) CH3 oil* 260d o MeO CH20-N=C(CH3) 2.6-diCI-4-pyrimidinyl 93-123 261 o MeO CH20-N=C(CH3) 3-CF3-4-Me0-Ph 112-121 WO 97/00612 PCT/US96/10326 130 262 O MeO CH20-N=C(CH3) 3-CF3-4-F-Ph oil* 263 O MeO O 5-Ph-1,3.4-oxadiazol-2-y 1 130-132 264 o MeO O 5-(4-Me-Ph)-1,3,4-oxadiazol-2- 150-151 yi 265 o MeO O 5-(4-Br-Ph)-1,3,4-oxadiazol-2- solid* yi 266 o MeO O 5-(4-Cl-Ph)-l ,3,4-oxadiazol-2- 130-132 Ex. 3 y! 267 o MeO O 5-(3-MeO-Ph)-l ,3,4-oxadiazol- 108-111 2-yi 268 o MeO O 5-(3-Me-Ph)-l,3.4-oxadiazol-2- 119-121 yi 269 o MeO O 5-(4-r-Bu-Ph)-l,3,4-oxadiazol- 159-161 2-yl 270 o MeO O 5-(3-F-Ph)-1,3,4-oxadiazol-2-yl 105-108 271 o MeO O 5-(4-F-Ph)-l,3,4-oxadiazol-2-yl 124-125 272 o MeO O 5-(3-Cl-Ph)-l,3,4-oxadiazol-2- 130-135 yi 273 o MeO O 5-(4-CF3-Ph)-l,3,4-oxadiazol- soiid* 2-yl 274 o MeO CH-)0—N s \ 101-105 xy* 275 o MeO O 3-(2-CN-PhO)-Ph oil* 276 o MeO 0 3-(2-N02-Ph0)-Ph oil* 277 o MeO 0 3-(3-N02*2-pyridinyl-0)-Ph oil* 278 o CI CH20-N=C(CH3) 4-CF3-2-pyridinyl 85-86 279 o MeO 0 5-(3-Br-Ph)-l .3,4-oxadiazol-2- 147-157 280 o MeO o yi 3-(3-N02-Ph)-1,2,4-thiadiazol- 169-170 5-yl 281 o MeO CH20-N=C(0CH3) 3,5-diCF3-Ph oil* 282 o MeO CH20-N=C(CH3)CH2S 3,5-diCF3-Ph oil* 283 o MeO CH20-N=C(CH3)CH20 3,5-diCF3-Ph oil* 284e o MeO CH20-N=C(CH3) 2,8-diCF3-quinolin-4-yl 149-151 WO 97/00612 PCT/US96/10326 131 :s5f O MeO CH20-N=C(CH3) 2.8-diCF-}-quinolin-4-yl 150-155 286 O MeO CH20-N=C(CH3) 5-Br-3-pvridinyl 120-122 287 O MeO O 3-(3-Cl-Ph)-l,2,4-thiadiazol-5- 121-122 yi 288 0 MeO O 3-(4-CF3-Ph)-1,2,4-thiadiazol- 135-136 5-yl 289 0 MeO O 3-(4-Me-Ph)-l,2,4-thiadiazol-5- 139-142 y! 290 0 MeO O 3-(4-Br-Ph)-1,2,4-thiadiazol-5- 137 y! 291 0 MeO O 3-(3-Me-Ph)-l,2,4-thiadiazol-5- 125-126 yi 292 0 MeO O 3-(3,4-diF-Ph)-1,2,4-thiadiazol- 140-141 5-yl 293 O MeO O 3-(3-Cl-4-Me-Ph)-1,2,4- 113-115 thiadiazol-5-yl 294 O MeO O 3-(3,5-diBr-4-MeO-Ph)-1,2,4- 178-179 thiadiazol-5-yl 295 O MeO O 3-(3,4-diCl-Ph)-1,2,4- 156-158 thiadiazol-5-yl 296 O MeO O 3-(3,5-diF-Ph)-1,2,4-thiadiazol- 142-144 5-yl 297 0 MeO O 3-(4-N02-Ph)-1,2,4-thiadiazol- 192-193 5-yl 298S O MeO CH20-N=C(SCH3) 3-CF3-Ph oil* 299 O MeO CH20-N=C(CH3)CH2S 2-benzothiazolyl oil* 300 O MeO CH20-N=C(0CH3) 2-naphthalenyl oil* 301 O MeO o 3-(4-CN-PhO)-Ph oil* 302 O MeO o 3-(4-N02-Ph0)-Ph oil* 303 O MeO 0 3-F-2-N02-Ph 118-120 304 O MeO o 6-(3-CF3-Ph)-pyrimidin-4-yl 123-126 305 O MeO 0 4-CF30-Ph oil* 306 O CI o 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 CH20-N=C(CH3)CH2S 3,5-diCl-Ph oil* WO 97/00612 PCT/US96/10326 132 309 0 MeO O 3-(4-CI-3-F-Ph)-l,2,4-thiadiazol-5-yl 137-138 310 O MeO O 3-(3-MeO-Ph)-l ,2.4-thiadiazol-5-yl 97-98 311 0 MeO O 3-(4-F-Ph)-1,2,4-thiadiazoI-5-yl * 312 o MeO O 5-(3,4-diCl-Ph)-1,3,4-oxadiazol-2-yl 152-155 313 o MeO O 6-(3,5-diCF3-Ph)-pyrimidin-4- yi 168-170 314 o MeO O 3-(2-pyridinyl-0)-Ph oil* 3i5 o MeO O 3-(2-pyrimidinyl-0)-Ph oil* 316 o MeO O 6-(4-Me-PhO) pyrimidin-4-yl oil* 317 o MeO 0 6-Cl-pyrazin-2-yl 135-137 Ex. 15 318 0 CI ch2s 5,7-diMe-6-Ph- [ 1,2,4]triazolo[ 1,5-a)pyrimidin-2-yl 121-124 319 0 MeO ch2s 5,7-diMe-6-Ph- [l,2,4]triazolo[l ,5-a]pyrimidin-2-yl 155-160 320 o MeO 0 3-(4-Ph-Ph)-l ,2,4-thiadiazol-5- yi 159-161 321 o MeO 0 3-(3-CF3-Ph)-1,2,4-thiadiazol -5-yl 122-123 322 o MeO o 3-(4-r-Bu-Ph)-l ,2,4-thiadiazol-5-yl 174-175 323 o MeO o 3-(3-Br-Ph)-1,2,4-thiadiazol-5- yi 137-139 324 o MeO 0 3-(3-Br-4-MeO-Ph)-1,2,4-thiadiazol-5-yl 161-162 325 0 MeO 0 3-(4-F-3-CF3-Ph)-1,2,4-thiadiazol-5-yl 164-165 326 0 MeO 0 3-(4-Br-3-Me-Ph)-1,2,4-thiadiazol-5-yl 160-162 327 0 MeO o 5-(4-MeO-Ph)-l ,3,4-oxadiazol-2-yl 180-181 WO 97/00612 PCT/US96/10326 133 328 O MeO O 5-(4-Ph-Ph)-1,3,4-oxadiazol-2- y! 329 O MeO O 3-(3,5-diCl-Ph)-1.2,4- thiadiazol-5-yl 330 O MeO O 5-(3,5-diCF3-Ph)-1,3,4- oxadiazol-2-yl 331 O MeO O 5-(2-F-Ph)-1,3,4-oxadiazol-2-y I 332 O MeO O 5-(2-Cl-Ph)-1.3.4-oxadiazol-2- yi 333 O MeO O 5-(2,4-diCI-Ph)-1,3,4- oxad:azol-2-yl 334 O MeO O 3-(4-MeS-Ph)-l,2,4-thiadiazol- 5-yl 335 o MeO O 3-(3-F-Ph)-l,2,4-thiadiazol-5-yl 336 o MeO O 3-CF3-Ph 337 o MeO O 5-(4-Cl-Ph)-l,3,4-thiadiazol-2- Ex. 18 yi 338 o MeO O 6-F-p>ridin-2-yl 339 0 MeO 0 6-(3-Me-PhO)-pyrimidin-4-yl 340 0 MeO ch2 3-(4-Cl-Ph)-1 //-pyrazol-1 -yl 341 0 MeO 0 3-(4-Cl-Ph)-l ,2,4-thiadiazol-5- yi 342 o MeO O 3-(4-CF30-Ph)-1,2,4- thiadiazol-5-yl 343 o MeO O 3-(3-CF30-Ph)-1,2.4- Ex. 2 thiadiazol-5-yl 344 o MeO O 3-(4-HCF20-Ph)-1,2,4- thiadiazol-5-yl 345 o MeO O 3-r-Bu-1,2,4-thiadiazol-5-yl Ex. 14 346 0 MeO CH20-N=C(CH3) 4-(CF3CH20)-3-CF3-Ph 347 o MeO CH20-N=C(OCH3) 3-Br-Ph 348 o MeO O 6-(4-CF3-Ph)-pyrimidin-4-yl 349 o MeO O 3-(2-CHO-PhO)-Ph 350 0 MeO O 3-(2-Me-Ph0)-2-N02-Ph 351 o MeO O 5-NOT6-PhO-pyridin-2-yl 179-180 159-160 175-176 139-140 139-140 181-182 solid* 116-118 solid* solid* 175-178 oil* 159-163 126-127 solid* 112-113 solid* 110-111 oil* oil* 163-165 106-108 131-133 127-130 WO 97/00612 PCT/US96/10326 134 352 O MeO 0 3-(2-Me-PhO)-Ph oil* 353 O MeO 0 3-c-Pr-1,2.4-thiadiazol-5-yl * 354 0 MeO 0 3-c-pentyl-1,2,4-thiadiazol-5-yl * 355 O CI ch2 3-(4-Cl-Ph)-1 //-pyrazol-1 -yl * 356 O MeO 0 4-(4-Cl-Ph)-1,2.5-thiadiazol-3- \/1 * 357 O MeO och2 y1 2-Cl-5-thiazolyl * 358 O MeO 0 6-(4-CF3-Ph)-2-pyrazinyl 145-148 Ex. 16 359 O MeO ch2o 5-CF3-2-pyridinyl 128-130 360 o MeO CH20-N=C(CH3) 3- [f-Bu0C(=0)]-Ph gum* 361 o MeO 0 6-(3,5-diCF3-Ph)-2-pyrazinyl 173-174 362 0 MeO 0 6-{2,4-diCl-Ph)-4-pyrimidinyl 170-175 363 o CI 0 3-(3-CF30-Ph)-1,2,4- * thiadiazol-5-yl 364 o CI 0 3-(3,4-diCl-Ph)-l,2,4- ♦ thiadiazol-5-yl 365 o CI 0 3-(3,5-diCl-Ph)-1,2,4- 149-150 thiadiazol-5-yl 366 o CI 0 3-(4-Br-Ph)-1,2,4-thiadiazol-5- 158-159 y! 367 o CI 0 3-(4-CF3-Ph)-1,2,4-thiadiazol- » 5-yl 368 o CI o 3-(4-/-Bu-Ph)-l ,2,4-thiadiazol- * 5-yl 369 o CI 0 3-r-Bu-1,2,4-thiadiazol-5-yl * 370 o MeO 0 6-PhO-2-pyridinyl oil* 371 0 MeO 0 3-(4-Me-Ph0)-2-N02-Ph 150-152 372 0 MeO 0 3-(2-C02Me-6-N02-Ph0)-Ph oil* 373 0 MeO CH20-N=C(SCH3) 3,5-diCF3-Ph solid* 374 0 MeO CH20-N=C(CH3) 4-Me3 Si-benzyl oil* 375 0 CI CH20-N=C(CH3) 4-Me3Si-benzyl oil* 376 0 MeO o 3-(3-CN-2-pyridinyl-0)-Ph 132-134 377 o MeO 0 6-Cl-3-N02-2-pyridinyl 146-151 378 0 MeO o 3-(3,5-diCF3-Ph)-Ph 52-57 379 0 MeO CH20-N=C(CH3) 4-(C02-n-Bu)-2-pyridinyl 106-108 WO 97/00612 PCT/US96/10326 135 380 0 MeO CH20-N=C(CH3) 4-(C02-/-Bu)-2-pyridinyI 147-149 381 O MeO O 5-(3-Br-Ph)-l,3,4-thiadiazol-2- vl oil* 382 0 MeO O y 3-(6-Cl-5-NO->-4-pyrimidinyI- 70-74 0)-Ph 383 0 CI O 2-naphthaleny! 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-0)-Ph oil* 387 0 MeO O 3-(2-C02Me-Ph-0)-Ph oil* 388 0 MeO O 3-(2,6-diCN-Ph-0)-Ph 65-68 389 0 MeO O 3-(3-Me-Ph-0)-Ph oil* 390 0 MeO O 4-(3-Cl-Ph)-1,2,5-thiadiazol-3- * yi 391 0 MeO ch2 3-(3-Cl-Ph)-ltf-pyrazol-l-yl * 392 0 MeO O 6-Cl-2-benzothiazolyl solid* 393 0 MeO O 5-MeS02-1,3,4-oxadiazol-2-yl * 394 0 CI O 5-MeS02-1,3,4-oxadiazol-?-yl * 395 0 CI O 3-(4-CF3 O-Ph)-1,2,4- * thiadiazol-5-yl 396 0 MeO O 5-(2-Br-Ph)-1,3,4-thiadiazol-2- * yi 397 0 MeO o 5-(2-Cl-Ph)-l,3,4-thiadiazol-2- * yi 398 0 MeO ch2s 5-Ph-2-benzoxazolyI 55 399 0 MeO och2 5,7-diCl-2-benzoxazolyl 173-175 400 0 MeO CH20-N=C(0CH3) 3-Br-5-I-Ph oil* 401 0 MeO CH20-N=C(0CH3) 3-F-5-CF3-Ph oil* 402 0 MeO ch2s 5-Cl-2-benzothiazolyI solid* 403 0 MeO 0 4-Cl-2-benzothiazolyl 178-181 404 0 MeO o 4-(3-CF3-Ph)-2-pyrimidinyl 50 405 0 MeO och2 5-(3-CF3-Ph)-1,2,4-oxadiazol - 148-150 3-yi 406 0 MeO och2 2-(4-Cl-Ph)-4-thiazolyl * 407 0 MeO 0 6-Cl-2-pyridinyl 161-163 408 0 MeO 0 3-(4-CF3-Ph)-Ph 149-152 WO 97/00612 PCT /U S96/10326 409 0 MeO O 410 0 MeO O 41 1 0 MeO O 412 0 MeO O 413 O MeO O 414 O MeO O 415 O MeO O 416 o MeO O 417 0 MeO O 418 o MeO O 419 o MeO O 420 o MeO O 421 0 MeO O 422 o MeO O 423 0 MeO o 424 0 MeO o 425 o MeO o 426 o MeO O 427 o ci o 428 o MeO o 429 o MeO o 430 o MeO ch2o 431 o MeO o 432 o MeO och2 433 0 MeO ch=n-n(ch3) 434 0 MeO ch=n-n(ch"3) 435 0 ci ch2s 436 0 MeO ch2s 136 6-(3,5-diCF3-Ph)-2-pyridinyl 176-178 5-(2-F-Ph)- l,3.4-thiadiazol-2-yl oil* 5-(4-Br-Ph)-1,3.4-thiadiazol-2- solid* yl 5-(4-i-Bu-Ph)-1,3,4-thiadiazol- solid* 2-yl 5-Br-4-(3,4-diF-Ph)-2-thiazolvl 155-157 3-(3,5-diCl-Ph)-Ph 145-147 3-(4-F-PhO)-Ph oil* 3-{4-F-Ph0)-2-N02-Ph 105-108 6-(2-Me-PhO)-2-pyridinyl oil* 3-(2-F-PhO)-Ph oil* 3-(4-N02-2-CF3-Ph0)-Ph oil* 3-(2-MeO-PhO)-Ph oil* 3-(2-MeO-Ph0)-2-NO2-Ph oil* 3-(3-N02-2-thienyl-0)-Ph oil* 3-(2-CF3-Ph0)-Ph oil* 3-(2,6-diMe-Ph0)-Ph oil* 5-(3,5-diCl-Ph)-1,3,4- * thiadiazoI-2-yI 2-Cl-4-pyrimidinyl 156-158 3-(4-CF30-Ph)-1,2,4- * thiadiazol-5-yl 5-(3-Cl-Ph)-1,3,4-thiadiazol-2- * yi 2-(3,5-diCF3-Ph)-4-pyrimidinyl 107-113 3-Ph-Ph gum* 5-Cl-2-pyrimidinyl 171-173 5-Ph-2-oxazolyl 150-152 3-CF3-2-pyridinyl 185-187 4-CF3-2-pyridinyI 169-171 4,5-dihydro-3-Ph-1,2,4-triazin- 79-95 6-yl 3-(3,5-diCl-Ph)-4,5-dihydro- 174-179 l,2,4-triazin-6-yl WO 97/00612 PCT/US96/10326 137 437 O MeO ch2s 4,5-dihydro-3-(3-CF3-Ph)-l,2,4-triazin-6-yl 63-72 438 O MeO O 6-(4-CF3-Ph)-2-pyridinyl 75-85 439 O MeO O 3-(3-CF3-Ph)-Ph 43-45 440 O MeO 0 3-(4-CN-Ph)-Ph 170-171 441 O MeO ch20-n=c(ch3) 4-Br-2-pyridinyl 96-99 442 O MeO ch20-n=c(0ch3) 3-CHCl2-Ph oil* 443 O MeO O 4-(3,5-diCF3-Ph)-2-pyrimidinyl 157-159 444 O MeO ch2° 2-Me-5-i-Pr-Ph 84-86 445 O MeO O 5-Br-2-thiazoIyl 153-156 446 O MeO o 5-(3-CF3-PhV2-thiazolyl 124-127 447 O MeO 0 3-(2-Br-PhO)-Ph oil* 448 O MeO 0 3-(2-Et-PhO)-Ph oil* 449 O MeO 0 3-Br-1,2,4-thiadiazol-5-yl * 450 O MeO ch2o 2-Cl-5-CF3-Ph 143-149 451 O MeO 0 5-(3-CF3-Ph)-2-pyrimidinyl 145-147 452 O MeO 0 3-(3-thienyl)-1,2,4-thiadiazol-5- yi solid* 453 O MeO 0 3-(2-thienyl)-1,2,4-thiadiazol-5- yi solid* 454 O MeO 0 5-(2,4-diCl-Ph)-1,3,4-thiadiazol-2-yl * 455 o MeO 0 5-(3,5-diCF3-Ph)-1,3,4-thiadiazol-2-y] * 456 O MeO 0 6-(4-CN-Ph)-4-pyrimidinyl 149-151 457 O MeO 0 6-(3-CF3-Ph)-2-pyrazinyl 118-121 458 O MeO 0 6-(4-CN-Ph)-2-pyrazinyl 195-199 Ex. 17 459 O MeO 0 6-(3-Cl-4-F-Ph)-2-pyrazinyl 147-149 460 O MeO ch20-n=c(ch3) 4-(C3=CH)-2-pyridinyl 99-102 461 o MeO o 5-Br-2-pyrimidinyl 172-174 462 0 MeO 0 3-(5-Br-2-thienyl)-1,2,4- * Ex. 12 thiadiazol-5-yI 463 0 MeO ch2s 3-(3-CI-Ph)-4,5-dihydro-5-Me-l,2,4-triazin-6-yl 65-78 WO 97/00612 PCT/US96/10326 464 0 ci ch2s 465 0 ci ch2s 466 0 MeO O 467 0 MeO O Ex. 19 468 O MeO O 469 O MeO o 470 O MeO O 471 O MeO O 472 O MeO O 473 O MeO o 474 O MeO O Ex. 13 475 O MeO O 476 O MeO O 477 o MeO O 478 O MeO o Ex. 20 479 o MeO ch20-n=c(ch3) 480 o MeO ch20-n=c(ch3) 481 o ci ch20-n=c(ch3) 482 O ci ch20-n=c(ch3) 483 o MeO ch20-n=c(ch3) 484 O MeO ch20-n=c(nh2) 485 o MeO 0 486 0 MeO ch2s 3-(3-Cl-Ph)-4.5-dihydro-5-Me- 171-172 1.2,4-tria2in-6-yl 3-(3,5-diC!-Ph)-l,2,4- 108-111 thiadiazol-5-yI 5-(4-CF3-Ph)-1,3,4-thiadiazol- * 2-yl 5-Br-4-(3-CF3-Ph)-2-thiazolyl gum* 7-MeO-2-naphthalenyI oil* 3-(2-CN-3-F-PhO)-Ph oil* 3-(2-CN-6-F-PhO)-Ph oil* 3-(2,6-diN02-Ph0)-Ph oil* 3-(2,5-diF-PhO)-Ph oil* 3-(2,5-diMe-PhO)-Ph oil* 3-(2,5-diCl-3-thienyl)-l,2,4- 144-147 thiadiazol-5-yl 3-(4-I-Ph)-1,2,4-thiadiazol-5-yl 167-168 3-(6-Cl-3-pyridinyl)-1,2,4- 169-170 thiadiazol-5-yl 3-(3-I-Ph)-1,2,4-thiadiazol-5-yl 171 -172 4-(3-CF3-Ph)-2-thiazolyl 116-118 3,4-dihydro-4,4-diMe-2//-l- oil* benzothiopyran-6-yl 3,4-dihydro-2//-l- oil* benzothiopyran-7-yl 3,4-dihydro-4,4-diMe-2//-l- oil* benzothiopyran-6-yl 3.4-dihydro-2//-l- oil* benzothiopyran-7-yl 3-(CF3CH20)-Ph gum* 3.5-diCF3-Ph 177-178 3-(4,5-diCl-2-thienyI)-l,2,4- solid* thiadiazol-5-yI 3-(3,5-diCI-Ph)-l,2,4- 193-195 thiadiazol-5-yl WO 97/00612 PCT/US96/10326 139 487 0 MeO CH2S 3-(3-CF3-Ph)-1,2,4-thiadiazol- 139-140 5 vl 488 O MeO O 3-(3,4,5-triCI-2-Lhienyl)-1,2,4- 175-177 thiadiazol-5-yl 489 O MeO O 3-(5-Cl-2-thienyl)-1.2,4- 130-131 thiadiazo]-5-yl 490 O MeO O 3-[3-(PhOC)-Ph]-l,2,4- * thiadiazol-5-yl 491 O MeO O 3-[3-(Me3SiC=C)-Ph]-l,2,4- 133-134 Ex. 6 lhiadiazol-5-yl 492 O MeO O 3-[3-(EtOCsC)-Ph]-1,2,4- solid* thiadiazol-5-yl 493 O MeO O 3-[3-(4-F-PhC=C)-Ph]-1,2,4- solid* thiadiazol-5-yl 494 O MeO O 3-[3-(2-pyridinyl-CsC)-Ph]- solid* l,2,4-thiadiazol-5-yl 495 O MeO o 3-[3-(tetrahydropyran-2-yl- solid* OCH2-CsC)-Ph]-1,2,4- thiadiazol-5-yl 496 o MeO o 3-[3-(t-Bu-OC)-Ph]-l ,2,4- 130-131 thiadiazol-5-yl 497 o MeO o 3-(3-CHO-Ph)-1,2,4-thiadiazol- * 5-yi 498 o MeO o 3-(2,5-diCl-PhO)-Ph 110-112 499 o MeO o 3-(3,5-diCl-PhO)-Ph oil* 500 O MeO ch2o 3-(4-CF3-Ph)-1,2,4-thiadiazol- 107-111 5-yl 501 0 MeO ch2o 3-(3,5-diCF3-Ph)-1,2,4- 132-136 thiadiazol-5-yl 502 0 MeO ch2o 2-(3-CI-4-MeO-Ph)-5-Me-4- 172-175 thiazolyl 503 O MeO o 3-(3-CF3-PhO)-Ph oil* 504 O MeO 0 3-(3-F-PhO)-Ph oil* 505 O MeO 0 3-(2,3-diF-PhO)-Ph oil* 506 o MeO 0 3-(2,4-diF-PhO)-Ph oil* WO 97/00612 PCT/US96/10326 140 507 0 MeO O 3-(3-HC=C-Ph)-1.2,4- Ex. 7 thiadiazol-5-yl 508 0 MeO O 3-(6-CF3CH20-3-pyridinyl)-1,2,4-thiadiazol-5-yl 509 o MeO O 6-(4-Cl-Ph)-2-pyrazinyl 510 o MeO O 6-(4-F-Ph)-2-pyrazinyl 511 o MeO O 6-Ph-2-pyrazinyl 512 o MeO CH20-N=C(CH3) 3-Et-Ph 513 o MeO ch2s 3-(3,5-diCF3-Ph)-l,2,4-th iadiazol-5-y I 514 o MeO 0 6-(4-Cl-Ph)-4-pyrimidinyl 515 o MeO 0 5-Me-4-(3-CF3-Ph)-2-thiazolyl Ex. 21 516 o MeO 0 6-(4-C02Et-Ph)-2-pyrazinyl 517 o MeO 0 3-(5-Br-3-pyridinyl)-1,2,4-thiadiazol-5-yl 518 o MeO 0 3-(2,6-diCl-4-pyridinyl)-1,2,4-thiadiazoI-5-yl 519 o MeO 0 4-Cl-5-CN-2-thiazolvl 520 o MeO 0 3-(2-furanyl)-1,2,4-thiadiazoI - Ex. 11 5-yl 521 o CI 0 A -CH2N N- (C%)3 2-thiazolyl 522 0 ci 0 A -ch2n n- (ch^O 3-CF3-Ph 523 0 MeO 0 2-thiazolyl A 177-178 solid* 156-158 151-153 135-136 81-85 157-159 115-120 oil* 119-127 188-189 148-149 119-122 107-108 95-100 125-130 166-170 -chon n-(CH2)3 WO 97/00612 FCT/US96/10326 141 524 O MeO O 3-CF3-Ph 130-135 /\ -chin n-(chth 525 0 MeO CH20 l,6-diBr-2-naphihalenyl 189-191 526 O MeO O 3-{5-Br-2-furanyI)-l ,2,4- solid* thiadiazol-5-yl 527 O MeO O 3-[3-PhC(=0)0-Ph]-l,2.4- * Ex. 8 thiadiazol-5-y! 528 O MeO O 3-(3-HO-Ph)-1.2.4-thiadiazol-5- solid* Ex. 9 yl 529 O MeO O 6-Ph-4-pyrimidinyl 123-125 530 O MeO O 3-(r-Bu-CHC)-l,2,4-thiadiazol- * Ex. 5 5-yl 531 O MeO O 3-(3-Et3SiO-Ph)-1,2,4- thiadiazol-5-yl 532 O MeO O 3-[3-(f-EuMe2SiO)-Ph]-l,2,4- * thiadiazol-5-yl 533 O MeO O 3-[3-Cl3CCH2OC(=0)0-Ph]- * l,2,4-thiadiazol-5-yl 534 O MeO O 3-(3-MeCHC10C(=0)0-Ph]- 1,2,4-thiadiazol-5-yl 535 O MeO O 3-[3-[CH2=CH0C(=0)0]-Ph]- " 1,2,4-thiadiazoI-5-yl 536 O MeO 0 3-[3-[f-BuC(=0)0]-Ph]-l,2,4- * thiadiazol-5-yl 537 O MeO 0 3-[3-[Me3Si(CH2)20CH20]- * Ph]-1,2,4-thiadiazol-5-yl 538 O MeO 0 3-[3-CF3S(0)20-Ph]-1.2,4- solid* Ex. 10 thiadiazol-5-yl 539 O MeO O 3-(2,5-diBr-3-thienyl)-1,2,4- solid* thiadiazol-5-yl 540 O MeO 0 3-(3-Cl-benzyl)-1.2.4- solid* thiadiazol-5-yl 541 O MeO O 3-(4-CI-benzyi)-1.2,4- solid* thiadiazol-5-yl WO 97/00612 PCT/US96/10326 142 542 0 MeO O 6-(4-F-Ph)-4-pyrimidinyl 65-70 543 0 MeO ch2s 3-(3.5-diCl-Ph)-5-Me-1,2.4- l96-'98 triazin-6-yl 544 0 MeO ch2s 4,5-dihydro-5-Me-3-Ph-1,2,4- 66-68 triazin-6-yl 545 0 MeO CH2S 5-Me-3-Ph-l ,2,4-triazin-6-yl 168-171 546 0 MeO ch2s 5-Me-3-(3-CF3-Ph)-1,2,4- 64-66 triazin-6-yl 547 0 MeO 0 3-(3-Me3SiO-Ph)-1,2,4- * thiadiazol-5-yl 548 O MeO 0 3-[3-(CH2=CHCH20)-Ph]- * 1,2,4-thiadiazo!-5-yI 349 O MeO 0 3-[3-(CH2=CBrCH20)-Ph]- * 1,2,4-ihiadiazol-5-yl 550 O MeO 0 5-Br-4-(3,5-diCl-Ph)-2- 153-155 thiazolyl 551 O MeO ch?s 3-(3-Cl-Ph)-5-Me-l ,2,4-triazin- 117-119 6-yl 552 O MeO CH20-N=C(CH3) /-Bu 96-98 553 O MeO ch2o cf3ch2 oil* 554 0 MeO 0 4-(3,5-diCI-Ph)-2-thiazolyl solid* 555 O MeO 0 4-(3,5-diCl-Ph)-5-Me-2- 60 thiazolyl 556 O MeO 0 3-[3-(ch2=ch)-Ph]-1.2,4- * thiadiazol-5-yl 557 0 MeO 0 3-[4-(4-F-PhCsC)-Ph]-1,2,4- 154-157 thiadiazoI-5-yl 558 0 MeO o 5-CN-2-Ph-4-thiazolyl 144-147 559 0 MeO o 3-Et-7-CF3-2-quinoxalinyl 138-141 560 0 MeO ch2o 3-Et-7-CF3-2-quinoxalinyl 155-157 561 0 MeO o 6-(4-C02Et-Ph)-4-pyrimidinyl 147-149 562 0 MeO 0 5-CI-4-(3-CF3-Ph)-2-thiazolyl gum* 563 0 MeO o 5-CN-4-Et2N-2-thiazolyl solid* 564 0 MeO o 5-Et-4-(3-CF3-Ph)-2-thiazolyi gum* 565h 0 MeO CH20-N=C(CH3) 3-CF3-Ph 84-87 566 0 MeO CH20-N=C(0CH3) 4-CF3-2-pyridinyl solid* WO 97/00612 PCT/US96/10326 143 567 O MeO O 3-|4-(HC=C)-Ph]-1,2,4- * thiadiazol-5-yl 568 O MeO O 3-(4-(Me3SiCaC)-Ph]-1.2.4- * thiadiazol-5-yl 569 0 MeO o 3-1-1,2.4-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- * ihiadiazol-5-yl 573 O MeO o 3-[3,5-bis- * [Me3Si(CH2)20CH20]-Ph]- 1,2,4-thiadiazol-5-y] 574 O MeO direct bond 3-(3-CF3-Ph)-1,2,4-oxadiazol- 114-115 5-yl 575 O MeO direct bond 5-/-Bu-1,3-benzodioxol -2-yl oil* 576 O MeO ch2o 1 -(2,4-diCl-Ph)-3-Me-1H- glass* pyrazol-4-yl 577 O MeO 0 3-[3,5-bis-[CF3CH20]-Ph]- * 1,2,4-thiadiazol-5-yl 578 O MeO ch2o 8-Br-3-Me-6-CF3-2- 130-184 quinoxalinyl 579 O MeO 0 8-Br-3-Me-6-CF3-2- 157-159 quinoxalinyl 580 O MeO CH2S-C(SCH3)=N 4-Br-Ph oil* 581 O MeO CH2S-C(SCH3)=N 3,5-diCl-Ph oil* 582 O CI ch2 3-(3,5-diCF3-Ph)-1,2,4- 94-103 oxadiazol-5-yl 645 O MeNH CH2ON=C(CH3) 3-Me3Si-Ph gum* 646 O MeNH CH20N=C(CH3) 3,5-diCF3-Ph 140-143 647 s cf3 CH2ON=C(CH3) 3-CF3-Ph 128-131 648 0 CF3 ch2o 2,5-diCH3-Ph 162-165 649 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 CH2ON=C(CH3) 3-CF3-Ph 102-106 652 0 Me2N CH2ON=C(CH3) 3-Me3Si-Ph oil* WO 97/00612 PCT/US96/10326 144 653 O Me CH2ON=C(CH3) 3-CF3-Ph oil* 65-4 O H direct bond ch3 solid* 655 o Et direct bond ch3 oil* a Compound contains 15% by weight of 4-[2-(bromomethyl)phenyl]-5- (difluoromethoxy)-2,4-dihydro-l-methyl-3//-l,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. 6 Compound isolated in a 1:2 ratio of geometric isomers. h Compound isolated as the Z isomer. *See Index Table M for JH NMR data. INDEX TABLE D N / V^W N—N \ CH3 Cmpd No. W X Y z m.D. (°C) 222 o MeO CH2ON=C(Me) 3-Me3Si-Ph oil/gum* 223 0 MeO ch2o 2,5-diMe-Ph 151-153 224 0 MeO direct bond CH2Br 117-118 225 o MeO CH2ON=C(Me) 3-CF3-Ph 91-93 226a o MeO CH=C(C1)C(=0)0 l-Bu 105-115 227b o MeO CH=C(C1)C(=0)0 /-Bu 104 228 0 MeO CH2ON=C(Me) 4-CF3-2-pyridinyl 101-103.5 583 0 MeO direct bond 3-(3-CF3-Ph)-1,2,4-oxadiazol-5-yl 158 584 0 MeO CH20-N=C(CH3) 3,4-diCI-Ph 132-134 585 o MeO CH20-N=C(NH2) 3-CF3-Ph 123-124 586 0 MeO CH20-N=C(CH3) 3,5-diBr-Ph 150.5-151 587 o MeO CH20-N=C(CH3) 3,5-diCl-Ph 159-160 WO 97/00612 PCT/US96/10326 145 588 0 MeO CH:0-N=C(CH3) 2-naphthalenyl 124-125 5S9C 0 MeO CH20-N=C(CH2CH3) 3-CF3-Ph oil* 590 o MeO ch2o 3-(4-CI-Ph)-l,2,4-thiadiazol-5-yl 184-185 591 0 MeO ch2o 3-(3.5-diCI-Ph)-l,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 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. cCompound contains 28% by weight of 2,4-dihydro-5-methoxy-2-methyl-4-[5-methyl-[[[[l-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]-3-thienyl]-3//-1,2,4-triazol-3-one which is also a compound of this invention. INDEX TABLE E n—n \ ch3 CrriDd W X Y Z m.D. (°C) 229 O MeO direct bond CH2Br 132-133 230 O MeO CH2ON=C(Me) 3,4-diCI-Ph 143-144 231 0 MeO CH2ON=C(Me) 3-Me3Si-Ph oil* 232 o MeO CH2ON=C(Me) 4-CF3-2-pyridinyl 123-125 233 o MeO CH2ON=C(Me) 3-CF3-Ph 87-89 *See Index Table M for *H NMR data. WO 97/00612 PCT/U S96/10326 146 INDEX TABLE F N—N \ CH3 Cmpd No. W X Y z m.p. CO 234 0 CI 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 CH20-N=C(CH3) 4-CF3-pyridin-2-yl 106-107 594 0 MeO CH20-N=C(CH3) 3,4-diCI-Ph 102-104 595 0 MeO CH20-N=C(CH3) 3-Me3Si-Ph 135-137 596 0 MeO CH20-N=C(CH3) 3,5-diCl-Ph 135-137 597 o MeO CH20-N=C(CH3) 3,5-diBr-Ph 145-147 598 o MeO CH20-W=C(NH2) 3-CF3-Ph 147-148 599 0 MeO CH2S 5-CF3-4H-1,2,4-triazol-3-yl 178-179 600 0 MeO direct bond 3-(3-CF3-Ph)-l,2,4-oxadiazol-5-yl 165-166 601 o MeO ch2 3-CF3-1 H-pyrazol-1 -yl 99-100 602 o MeO ch2o 2-Cl-5-CF3-Ph 106-108 603 o MeO ch2o 2,5-diCH3-Ph 91-93 604* A I o MeO CH20-N=C(CH3) 2-naphthalenyl semisolid* 605 o MeO 0 3-PhO-Ph 113-114 606 o CI 0 3-PhO-Ph 72-75 *See Index Table M for 'H NMR data. WO 97/00612 PCT/US96/10326 147 index table g O- xtr N—N \ ch3 Cmpd No. X Y Z m.p. (°C) 607 MeO direct bond 3-(3-CF3-Ph)-1,2,4-oxadiazol-5-yl 149-150 608 MeO direct bond CHoBr 147-149 609 MeO CH20-N=C(CH3) 2-naphthalenyl 134-136 610 MeO CH20-N=C(CH3) 3,4-diCI-Ph 118-119 611 MeO CH20-N=C(CH3) 4-CF3-pyridin-2-yl 125-127 612 MeO CH20-N=C(CH3) 3,5-diCl-Ph 148.5-150.5 613 MeO CH20-N=C(CH3) 3-Me3Si-Ph oil* 614 MeO CH20-N=C(NH2) 3-CF3-Ph semisolid* 615 MeO CH20-N=C(CH3) 3-CF3-Ph 81-83 616 MeO CH20-N=C(CH3) 3,5-diBr-Ph 126.5-127.5 *See Index Table M for NMR data. INDEX TABLE H \ CH3 Cmpd No. X Y Z 617 CI O Me 618 MeO O 3-(4-CF3-Ph)-1,2,4-thiadiazol-5-yl 619 MeO O 3-(3,5-diCl-Ph)-l,2,4-thiadiazol-5-yl 621 MeO O 3-(4-CI-Ph)-1,2,4-thiadiazol-5-y I m.p. f°C) i42-m3 216-217 ->->->.223 226-227 621 Cmpd 622 Cmp< 623 624 625 626 627 628 629 630 631 632 633 PCT/US96/10326 148 MeO O Me 180-181 INDEX TABLE I CH3 X Y Z m.p. CO MeO CH20-N=C(CH3) 3-CF3-Ph 153-155 index table j x r9 r10a y m.p. (°c) ci h h ch2o 159-162 ci 5-Me 7-Me ch2o 204-209 ci 6-ci h ch2o 175-181 MeO 5-Me 7-Me ch2o 187-197 MeO 7-MeO h ch2o 207-210 MeO 6-br 7-Me ch2o 205-209 MeO 5-Me h ch2o 205-208 MeO 5-Me 6-Me ch2o 210-214 MeO 5-Me 7-Me 0 210-216 MeO 7-MeO h 0 191-192 MeO 7-c1 h choo 225-229 WO 97/00612 PCT/US96/10326 149 634 MeO 6-Me 7-Me 0 218-219 635 MeO 5-Me H O 195-199 636 MeO 6-Br 7-Me 0 187-189 637 MeO 7-F H O 221-226 638 MeO 7-F H CH20 181-184 639 MeO H H O 230-233 640 MeO H H CHoO 190-195 N—N \ 8 RlOa wherein R^ is H or R^ Me Cmpd No. X Rl3 R9 R10a Y m.p. (°C) 641 MeO rt-Bu 6-1 8-1 ch2o 166-169 642 MeO n-Pr 6-Br 8-Br ch2o 160-163 643 MeO Me 6-1 h ch2o 200-204 644 MeO n-Bu 6-1 8-1 0 165-167 Cmpd No. 656 657 X MeO MeO 5-C1 5-CI index table l R43 4 I x~tV° N—N wherein R^3 is H orR4 \ CH3 R4a Y Z H O 3-(3-CF30-Ph)-l,2,4-thiadiazol-5-yl H O 3-(3,4-diCI-Ph)-1,2,4-thiadiazol-5-yl m.p. C°C) 154-155 65S 659 660 661 662 663 664 665 666 667 668 669 670 671 672 673 674 675 676 677 678 679 680 Ex. 681 682 683 684 685 686 687 688 689 690 691 PCT/US96/10326 150 MeO 5-C1 H O 3-(3,5-diCl-Ph)l,2.4-thiadiazol-5-vl # MeO 5-C1 H O 3-(3,5-diCF3-Ph)-l,2,4-thiadiazol-5-vl * MeO 5-C1 H O 3-(4-Br-Ph)-l,2,4-thiadiazoI-5-yl 166-168 MeO 5-C1 H O 3-(4-CF3*Ph)-1,2,4-thiadiazol-5-yl * MeO 5-C1 H O 3-(4-/-Bu-Ph)-1,2,4-thiadiazol-5-yl 159-160 MeO 5-C1 H O 3-r-Bu-1,2,4-thiadiazol-5-yl * MeO 3-C1 H O 3-(4-Br-Ph)-l,2,4-thiadiazol-5-yl * MeO 3-C1 H O 3-(3,4-diCl-Ph)-l,2,4-thiadiazol-5-yl * MeO 3-C1 H O 3-(4-CF3*Ph)-1,2,4-thiadiazoI-5-yl 120-124 MeO 3-C1 H O 3-(3-CF30-Ph)-1,2,4-thiadiazol-5-y 1 * MeO 3-C1 H O 3-r-Bu-1,2,4-thiadiazol-5-yl * MeO 3-C1 H O 3-(3,5-diCl-Ph)-l,2,4-thiadiazol-5-yl 130-135 MeO 3-C1 H O 3-(3,5-diCF3-Ph)-l,2,4-thiadiazol-5-yl * MeO 3-C1 H O 3-(4-r-Bu-Ph)-1,2,4-thiadiazol-5-yl * MeO 6-ch3 H O 3-(3,5-diCl-Ph)-1,2,4-thiadiazol-5-yl 152-158 MeO 6-ch3 H O 3-(3,4-diCl-Ph)-1,2,4-thiadiazol-5-yl 162-164 MeO 6-ch3 H O 3-(3-CF3-Ph)-1,2,4-thiadiazol-5-yl 119-120 MeO 6-ch3 H O 3-(3,5-diF-Ph)-1,2,4-thiadiazol-5-yl 124-126 MeO 6-ch3 H O 3-(3-CH3-Ph)-1,2,4-thiadiazol-5-yl 109-111 MeO 6-ch3 H O 3-(3-CF30-Ph)-1,2,4-thiadiazol-5-yl 91-93 MeO 6-ch3 H O 3-(4-CH3-Ph)-1,2,4-thiadiazol-5-yl 123-125 MeO 6-ch3 H O 3-(4-CF3-Ph)-1,2,4-thiadiazol-5-yl 109-111 MeO 6-ch3 H O 3-(3,5-diCF3-Ph)-1,2,4-thiadiazoI-5-yI 95-98 MeO 6-ch3 H O 3-(2-CH3-PhO)-Ph oil* MeO 6-ch3 H O 3-PhO-Ph oil* MeO 6-ch3 H O 3-(2-Cl-PhO)-Ph oil* MeO 6-ch3 H O 3-(2-F-PhO)-Ph oil* CI 6-CH3 H ch2o 3-(4-CF3-Ph)-1,2,4-thiadiazol-5-y 1 130-132 CI 6-ch3 H bond CH2Br 120-121 MeO 6-ch3 H O 6-(2-ch3-PhO)-4-pyrimidinyl 135-136 MeO 6-ch3 H O 3-(4-F-PhO)-Ph oil* MeO 6-ch3 H 0 3-(2,6-diF-PhO)-Ph oil* MeO 4-ch3o H 0 3-(4-CF3-Ph)-l,2.4-thiadiazol-5-yl 110-112 MeO 4-ch3o H 0 3-(3,5-diCF3-Ph)-l,2,4-thiadiazol-5-yl 107-110 692 693 694 695 696 697 698 699 700 701 702 703 704 705 706 707 708 709 710 711 712 713 714 715 716 717 718 719 Ex. 720 721 722 PCT/US96/10326 MeO 6-ch3 h O MeO 6-ch3 h O MeO 4-ch3o h O MeO 4-ch3o h O ci 6-ch3 h O ci 4-ch3o h O MeO 6-ch3 h O MeO 6-ch3 h O MeO 4-ch3o h O MeO 6-ch3 h O MeO 4-ch3 h ch2 MeO 6-ch3 h O MeO 6-ch3 h O MeO 4-ch3o h O MeO 6-ch3 h O MeO 6-ch3 h O MeO 6-ch3 h 0 MeO 6-ch3 h 0 CI 6-C02Me h bond CI 6-C02Me h bond MeO 4-ch3o h O MeO 6-ch3 h 0 MeO 6-ch3 h 0 MeO 6-ch3 h 0 MeO 6-ch3 h 0 MeO 6-ch3 h 0 MeO 6-ch3 h 0 MeO 6-Et h 0 MeO 6-ch3s h 0 MeO 6-ch3s h 0 MeO 6-ch3s h 0 51 3-(2,6-diCI-4-pvridinyl)-1,2,4- oil/solid' thiadiazol-5-yl 3-(2.6-diCl-benzyl)-1.2,4-thiadiazol-5- 128-129 yi 3-(2,6-diCl-4-pyridinyl)-1,2,4- 150-156 thiadiazol-5-yl 3-(2,6-diCl-benzyl)-l,2,4-thiadiazol-5- 113-119 y! ch3 132-134 ch3 144-146 6-Cl-4-pyrimidinyl 108-110 3- r-Bu-1,2,4-thiadiazol-5-yl 146-147 3-/-Bu-1,2,4-thiadiazol-5-yl oil* 6-(3,5-diCF3-Ph)-4-pyrimidinyl 195-198 3-cf3-1 W-pyrazol-1 -yl 368** 6-(4-CF3-Ph)-4-pyrimidinyl 148-150 6-(4-CF3-Ph)-2-pyrazinyl 128-131 3-(3,5-diCl-Ph)-1,2,4-thiadiazol-5-yl 173-176 6-(3-cf3-Ph)-2-pyrazinyl 118-120 3-F-2-N02-Ph oil* 6-(3,5-diCF3-Ph)-2-pyrazinyl 185-187 6-Cl-2-pyrazinyl 122-124 CH2Br 168-170 CHBr2 129-131 3-(3,5-diF-Ph)-l,2,4-thiadiazol-5-yl 149-153 6-(4-C02Et-Ph)-4-pyrimidinyl 97-103 6-(4-C02Et-Ph)-2-pyrazinyl 158-161 6-(3-CF3-Ph)-4-pyrimidinyl 125-127 6-Ph-2-pyrazinyl 137-139 6-{4-Cl-Ph)-2-pyrazinyl 166-171 6-(2-Br-PhO)-4-pyrimidinyl 127-129 3-(3,5-diCF3-Ph)-l,2,4-thiadiazol-5-yl 136-138 3-(3,5-diCF3-Ph)-1,2,4-thiadiazol-5-yl 154-156 3-(3,5-diCl-Ph)-l,2,4-thiadiazol-5-yl 204-208 3-(3,5-diF-Ph)-l,2,4-thiadiazol-5-yl 164-166 WO 97/00612 PCT/US96/10326 152 723 MeO 6-Et H O 3-(3,5-diCl-Ph)-I,2,4-thiadiazol-5-y) 139-142 724 MeO 6-Et H O 3-(3.5-diF-Ph)-l,2,4-thiadiazol-5-yl 115-119 725 MeO 6-CHO H O 3-(3,5-diF-Ph)-I,2,4-thiadiazol-5-yI 125-12S 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-thiadiazol-5-yl 43-55 728 MeO 6-CH3S H O 3-(4-CH3-Ph)-1,2,4-thiadiazol-5-yl 138-140 729 MeO 6-CHO H O 3-(3,5-diCl-Ph)-l,2,4-thiadiazol-5-yl 180-185 730 MeO 6-CHO H O 3-(3,5-diCF3-Ph)-1,2,4-thiadiazol-5-yl 144-146 731 MeO 6-CHO H O 3-(4-CH3*Ph)-1,2,4-thiadiazol-5-yI 118-123 *See Index Table M for 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. 5 INDEX TABLE M Cmpd No. *H NMR Data (CDCI3 solution unless indicated otherwise)3 2 5 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 6 7.32(m,7H), 6.99(m,2H), 5.08(s,2H), 3.84(s,3H), 3.42(s.3H). 4 8 7.25(m,4H), 3.98(s,3H), 3.45(s,3H). 2.30(s,3H). 5 5 7.61(d,lH), 7.35(m,3H), 7.1 l(m.2H). 6.84(t,2H), 5.12(s,2H), 3.96(s,3H), 3.4]5(s,3H), 2.24(s,3H). 14 5 7.65(d,lH), 7.45(m,2H), 7.23(m,lH), 7.10(m,2H). 6.82(t,lH), 6.78(d,lH). 5.08(s,2H), 4.29(m,2H), 3.41(s,3H), 2.24(s,3H), 1.31(t,3H). 17 5 7.6-7.45(m,5H), 7.20(m,lH), 7.14(d,2H), 5.27(d,lH), 5.16(d,lH), 3.46(s,3H), 2.34(s,3H), 2.16(s,3H). 19 8 7.6(d,lH), 7.5(m,3H), 7.4(t.lH), 7.25(m,lH), 7.15(d,2H), 5.26(d.lH), 5.20(d,lH), 3.48(s,3H), 2.41(s,3H), 2.43(s,3H), 2.18(s,3H). 20 87.62(m,2H), 7.5(m,2H), 7.35-7.2(m,4H), 5.25(d,lH), 5.15(d,lH), 3.48(s,3H), 3.02(m,2H), 2.85(m.2H). 21 57.42(m,2H), 7.10(m,lH), 7.06(m,3H), 6.99(t,lH), 6.68(d,2H), 3.37(s,3H), 2.51(s,3H). 23 88.01(s,lH), 7.61(d,lH), 7.52(m,4H), 7.35(m,3H), 7.25(d,lH), 5.23(d,IH), 5.15(d, 1H), 3.49(s,3H). 24 87.6(m,2H), 7.5-7.4(m,3H), 7.3-7.2(m,3H), 5.24(d,lH), 5.20(d,lH), WO 97/00612 PCT/US96/10326 153 3.48(s,3H), 2.40(s,3H). 25 5 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,lH), 5.00(d,IH), 3.45(s,3H). 26 8 7.6(d,lH), 7.45(m,2H), 7.33(t.2H), 7.19(m.2H). 7.10(t.lH), 7.01 (d,2H), 6.6(m,3H), 5.03(m,2H), 3.87(s.3H), 3.39(s,3H). 35 5 7.6-7.4(m,7H), 7.23(d,lH), 5.28(d,lH), 5.17(d.IH), 3.46(s,3H), 2.14(s,3H). 36 8 7.80(d,2H), 7.65-7.45(m,6H), 7.36(d,2H), 7.30(m,lH), 7.25(m,lH), 7.10(t,lH), 5.15(d,lH), 5.10(d,lH), 3.45(s,2H). 38 8 7.77(d.2H), 7.6(m,2H), 7.47(m,4H), 7.35(m,3H), 7.25(m,lH), 7.10 (m,lH), 5.13(d,lH), 5.12(d.lH), 3.89(s,3H), 3.38(s,3H). 39 8 8.03(s,lH), 7.70(d,lH), 7.53(m.2H), 7.35-7.25(m,5H), 5.06(s,2H), 3.46(s,3H). 40 8 7.6-7.5(m,3H). 7.24(m,lH), 7.13(s,lH), 7.02(d,lH), 6.78(d,lH). 5.96(s,2H), 5.26(d,lH), 5.14(d,lH), 3.48(s,3H), 2.13(s,3H). 41 8 8.04(s,lH), 7.8(m,lH), 7.45(m,2H)7.35-7.25(m,5H), 5.10(s,2H). 3.86(s,3H), 3.41(s,3H). 42 8 7.58(m,lH), 7.43(m,2H). 7.25(m,lH), 7.15(m,lH), 7.02(d,lH), 6.76(d,lH), 5.96(s,2H), 5.22(d,lH), 5.18(d,lH)3.89(s,3H), 3.42(s,3H), 2.15(s,3H). 43 8 8.40(s,lH), 7.6(m,lH), 7.5-7.4(m,5H), 7.3(d,lH), 7.18(m,2H), 6.38(s,lH), 3.45(s,3H). 45 8 7.55(d,lH), 7.40(m,3H), 7.20(m,4H), 5.21(d,lH), 3.87(s,3H), 3.42(s,3H), 2.24(s,3H). 47 5 7.6-7.2(m,9H), 5.4-5.2(m,2H), 3.87,3.83(s,3H), 3.41,3.40(s,3H). 48 8 7.6(m,3H), 7.44(m,2H), 7.35(m,3H), 7.25(m,lH), 5.26(d,lH), 5.22(d,lH), 3.88(s,3H), 3.49(s,3H), 2.20(s,3H). 49 8 7.5(d,lH), 7.40(m,4H), 7.23(m,2H), 7.18(d,lH), 5.26(d,lH), 5.21(d,lH), 3.88(s,3H)3.41(s,3H), 2.36(s,3H). 2.19(s.3H). 50 8 7.56(m,3H), 7.45(m,2H), 7.25(m,lH), 6.86(d,2H), 5.24(d,lH), 5.19(d,lH), 3.88(s,3H), 3.81(s,3H), 3,41(s,3H), 2.17(s,3H). 51 8 7.5(m,2H), 7.45(m,3H), 7.3(m,3H), 5.27(d, 1H), 5.22(d,IH), 3.89(s,3H). 52 8 8.02,8.01 (s,lH), 7.8.7.7(m,lH), 7.45(m,2H), 7.35(m,4H), 7.25(m,2H), 5.25(m,lH), 3.88,3.74(s,3H), 3.45.3.39(s,3H). 1,62-1.56(m.3H). 53 8 8.04(s,lH), 7.81(m,lH), 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). WO 97/00612 PCT/US96/10326 !54 54 5 7.35im.4H). 7.2()(m.2H), 7.05(d,2H), 6.95(d,lH>, 3.46(s,3H). 55 5 7.6-7.45im.3H), 7.2(m.lH). 4.67<d.lH). 4.48(d,lH), 3.56(s,3H). 56 57.5(m.lH), 7.44(m,2H). 7.22(m.lH). 4.60(d.lH), 4.36fd.lH), 3.96(s,3H), 3.47(s,3H). 60 5 7.72(d,2H), 7.58(d,3H), 7.50(m,2H), 7.26(m.lH). 5.30(d.lH). 5.24(d,lH), 3.48(s,3H), 2.42(s.3H), 2.21(s,3H). 61 8 7.70(m,2H), 7.60(m.2H), 7.43(m.3H), 7.23(m,lH). 5.30(d.lH). 5.25(d,lH), 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.lH), 3.80(s.3H). 339(s,3H). 64 5 8.40(s,lH), 7.5-7.2(m,7H), 7.02(,1H), 6.33(s,lH)3.78(s,3H), 3.36(s,3H), 2.18(s,3H). 65 8 8.42(s,lH), 7.55-7.26(m,7H). 7.16(d.2H), 6.36(s,lH), 3.79(s.3H)3.36fs,3H). 69 5 7.6-7.3(m,7H), 7.25(m,lH), 5.24(d,lH), 5.21(d,lH)3.89(s,3H), 3.41(s,3H), 2.18(s,3H), 1.31(s,9H). 70 8 7.60(d,lH), 7.45-7.38(m,3H), 7.35-7.20(m,2H), 7.1 l(d,lH), 5.74(d,lH), 5.21(d,lH), 3.88(s,3H). 3.41(s.3H), 2.27(s,3H), 2.26(s,3H), 2.18(s,3H). 75 8 8.56(s,lH), 7.58(m,lH). 7.40(m,3H), 6.99(s.lH), 3.43(s.3H). 76 8 7.66(d,2H), 7.58(m,5H). 7.5-7.3(m,5H), 7.25(m,lH), 5.28(d,lH), 5.24(d,lH), 3.90(s,3H), 3.47(S,3H), 2.23(s.3H). 77 S7.68(d, 1H), 7.6-7.5(m,2H), 7.25(m.lH), 7.00(d,lH). 6.68(d,lH), 6.61(s,lH), 5.05(d,lH), 5.00(d.lH), 3.49(s,3H), 2.29(s,3H), 2.16(s.3H). 82 5 8.02(s,2H), 7.82(s,lH), 7.6-7.45(m,3H), 7.25(m,lH), 5.33(d,lH), 5.21(d,lH), 3.50(s,3H), 2.23(s.3H), 84 8 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,lH), 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)](3H). 88 8 7.60(m,2H), 7.40(m,4H), 7.26(m,2H), 5.25(d, 1H), 5.22Cd, 1H), 3.88(s,3H), 3.40(s,3H), 2.20(s,3H), 1.33(s.9H). 89 8 7.80(s, 1H), 7.58(m,5H), 7.40(m,6H), 7.25(m,lH), 5.25(m,2H), 3.87(s,3H), 3.39(s,3H), 2.25(s,3H). 90 8 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.lH), 3.89(s.3H), 3.41Cs,3H). 2.17(s,3H). 1.33(d,6H). 94 S7.67(s.lH). 7.60-7.45(m.3H), 7.41(s,2H), 7.22(m,lH). 5.30(d,lH), WO 97/00612 PCT/US96/10326 155 5.16(d,IH), 3.49(s.3H), 2.14(s,3H). 96 5 7.S0(m.2H), 7.58(m,2H), 7.50(m.3H), 7.25(m,lH), 5.2S(d.IH), 5.25(d,lH), 3.89(s,3H), 3.40(s.3H), 2.22(s.3H). 99 5 7.82(s, 1H), 7.79(d,lH), 7.58(m.2H). 7.45(m.3H), 7.25(m,lH), 5.22(m,2H), 3.89(s,3H), 3.41(s.3H), 2.77(q,2H). 1.10(t,3H). 100 5 8.45(s,lH), 8.20(m,IH), 7.95(d,lH), 7.6-7.4^,4H), 7.25(m.lH), 5.30(d,lH), 5.26(d,lH), 3.90(s,3H), 3.41(s,3H), 2.24(s,3H). 110 8 7.60(d,lH), 7.45(m,2H), 7.25(m,lH), 7.20(s,2H), 7.00(s,lH), 5.25(d,lH), 5.21(d,lH), 3.88{s,3H), 3.41(s,3H), 2.32(s.6H), 2.18(s,3H), 111 8 7.8(m,lH), 7.75(m,lH), 7.6-7.4(m,5H), 7.2(m,lH), 5.33(d,lH), 5.17(d,lH), 3.45(s,3H), 2.18(s,3H). 112 Major Isomer: 8 7.6-7.4(m,3H), 7.34-7.20(m,5H), 5.24(d,lH), 5.14(d,lH), 3.46(s,3H), 2.10(m,lH), 0.90(m,2H), 0.55(m,2H). 113 8 7.89(s,lH), 7.80(d,lH), 7.60(m,2H), 7.43(m.3H), 7.25(m,lH), 5.28(d,lH), 5.24(d,lH), 3.90(s,3H), 3.42(s,3H), 2.19(s,3H). 114 8 8.6(d,lH), 8.0(d,lH), 7.6(m,2H), 7.5(m,3H), 7.2(m,lH), 5.48(d,lH), 4.6(d,lH), 3.56(s,3H), 3.4(s,3H). 115 8 7.64(s,lH), 7.58-7.42(m,4H), 7.30(m,lH), 7.25(m,lH), 5.29(d,lH), 5.24(d,lH), 3.90(s,3H), 3.41(s,3H), 2.19(s,3H). 121 8 7.6-7.4(m,5H), 7.36(t,lH), 7.20(m,2H), 5.30(d,lH), 5.18(d,lH), 3.47(s,3H), 2.17(s,3H). 123 8 7.72(d,2H), 7.58(d,2H). 7.51(m,lH), 7.34(m,3H), 5.31(s,2H), 3.94(s,3H), 3.43(s,3H), 2.24(s.3H). 125 8 7.62(m,lH), 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,lH), 7.49(m,3H), 7.34(m,3H), 7.22(m,lH), 5.28(s,2H), 3.94(s,3H), 3.44(s,3H), 2.2(s,3H). 127 8 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 8 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 8 7.59(m,2H), 7.52(m,lH), 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 8 7.92(m,IH), 7.84(d,lH), 7.6(m,lH), 7.47(m.2H), 7.33(m,3H). 5.30(s,2H), 3.98(s,3H), 345(s.3H), 2.23(s,3H). WO 97/00612 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 153 154 PCT/US96/10326 156 5 7.73(d,2H), 7.62(d.2H). 7.50(m,lH). 7.35(m.3H). 5.3l(s.2H). 3.96(s,3H). 3.44(s,3H), 2.23(s,3H). 5 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). 8 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). 57.51(m,3H). 7.33(m.3H), 7.l8(d,lH), 7.06(m.lH), 6.76(d,lH), 5.95(s,2H), 5.24(s,2H), 3.94(s,3H), 3.43(s,3H), 2.18(s,3H). 87.53(m,lH), 7.40(s,lH), 7.34(m,4H), 7.1(d.lH), 5.26(s,2H), 3.93(s.3H), 3.43(s,3H), 2.26(s,3H), 2.25(s.3H), 2.21(s,3H). 5 7.72(d,lH), 7.44(m,3H), 7.33(m,3H), 5.28(s,2H), 3.96(s,3H), 3.44(s,3H), 2.19(s,3H). 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). 7.63(m,lH), 7.54(m,lH), 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). 5 8.07(s,2H), 7.83(s,lH), 7.51(m,lH), 7.35(m,3H), 5.35(s,2H), 3.96(s,3H), 3.44(s,3H), 2.27(s,3H). S7.53(d,lH), 7.34(m,3H), 7.24(m,lH), 7.18(m,2H), 6.89(m,lH), 5.28(s,2H), 3.94(s,3H), 3.82(s.3H), 3.44(s,3H). 2.22(s,3H). 5 7.83(t,lH), 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). 5 7.56(m,3H), 7.33(m,5H), 7.13(m,lH), 6.99(m,4H), 5.26(s,2H), 3.94(s,3H), 3.43(s,3H), 2.22(s,3H). 5 8.57(d,lH), 7.85(d,lH), 7.65(t,lH), 7.53(d,lH), 7.3-7.4(m,3H), 7.22(t,lH), 5.32(s,2H), 3.95(s,3H), 3.44(s,3H), 2.3(s,3H). 5 7.54(m,lH), 7.32(m,3H), 7.2(t.lH), 6.95(m,2H), 6.73(m.lH), 5.27(s,2H), 3.91(s,3H), 3.43(s,3H), 2.95(s,6H), 2.22(s.3H). 5 7.52(m,3H), 7.34(m.4H), 7.18(m,lH), 5.29fs,2H), 3.94(s,3H), 3.43(s,3H), 2.22(s,3H). 5 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). 5 7.5(m,lH), 7.34(m,7H), 7.26(m,lH), 7.1 l(m,lH), 6.97(m,2H), 5.25(s,2H), 3.92(s,3H), 3.42(s,3H), 2.2(s,3H). 5 7.53(m,lH), 7.33(m.3H), 7.24(m,lH), 7.15(m,2H). 6.86(m.lH), 5.27(s.2H), 4,57(m.lH), 3.92(s,3H), 3.43(s.3H). 2.21(s,3H). 1.33(d,6H). WO 97/00612 PCT/US96/10326 157 155 5 7.49(m,3H), 7.34(m,4H), 5.29(s.2H), 3.95(s,3Hl, 3.44(s,3H), 2.18(s,3H). 156 5 7.S7(d,lH), 7.78(d,lH), 7.6(m,lH), 7.5(m.2H), 7.33(m.3H). 5.3(s.2H), 3.95(s,3H), 3.44(s,3H), 2.77(q,2H), 1.12(t,3H). 157 5 7.47-7.45(m,lH), 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), 5.10and 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 5 7.82(d,2H), 7.77(d,lH), 7.58(m,5H). 7.45(t,lH), 7.34(m.3H). 5.31(s,2H), 3.92(s,3H), 3.42(s,3H)2,29(s.3H). 160 6 7.48(m,3H), 7.33(m,6H). 7.23(m.lH), 7.14(d,lH), 7.00(d,lH), -" ' 5.26(s,2H), 3.93(s,3H), 3.42(s.3H), 2.2(s.3H). 161 5 7.66(s.lH), 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 5 7.53(d,lH), 7.35(m.3H). 7.24(m,2H), 6.98(s,lH). 5.27(s,2H), 3.92(s,3H), 3.43(s,3H), 2.31(s.6H), 2.21(s,3H). 164 5 7.45-7.55(d,lH), 7.30-7.35(m,3H), 6.45(d.lH). 6.05(d,lH), 5.26(s,2H), 3.96(s,3H), 3.43(s.3H), 2.33(s.3H), 2.13(s,3H). 165 6 7.52(d,lH), 7.45(s,lH), 7.37-7.31(m.3H), 6.92(s,lH), 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 5 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,lH), 2.22(s,3H), 1.78(m,6H). 1.41(m,4H). 168 5 8.57(s,lH), 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 5 8.45(t,lH), 7.80(t,lH), 7.57(s,lH), 7.33-7.50(m.6H), 5.35(s,2H), 3.89(s,3H), 3.43(s,3H), 2.33(s,3H). 171 8 7.69(d,2H), 7.62(m,IH), 7.49(m.lH), 7.34(m.3H). 5.29(s.2H), 3.96(s,3H), 3.45(s,3H), 2.17(s,3H). 172 8 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 8 7.47(d, 1H), 7.30-7.39(m,3H), 7.19(s,l H), 6.79(s,lH), 5.30(s,2H), 3.97(s,3H), 3.91(s,3H), 3.45(s,3H), 2.15(s,3H). 176 Major isomer: 87.69ft, 1H). 7.57(d,2H). 7.35Cm,4H). 5.17(s,2H). 4.03(s,3H), 3.97(s,3H), 3,45(s,3H). Minor isomer: 8 7.7(t,lH), 7.6(d,2H), 7.50(m,4H), 5.1 l(s.2H). 3.88(s.3H). 3.73(s,3H), 3.43(s.3H). WO 97/00612 PCT/US96/10326 158 177 5 7.53(m, 1H), 7.45(mlH), 7.42(m.lH). 7.34(m,3H), 7.24(m,lH). 7.17(mlH), 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 5 7.60-7.30(m,7H), 5.29(s,2H), 3.95(s,3H). 3.94(s.3H). 3.44(s,3H). 2.3(As,3H). 179 8 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,lH), 7.83(m,4H), 7.97(d,lH). 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,lH). 181 8 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,lH), 7.70(m,lH), 7.75(m,lH), 7.83(m,lH). 7.905(s,lH), 182 8 2.33(s,3H), 3.44(s,3H), 3.95(s,3H), 5.33(s,2H), 7.35(m,3H), 7.55(rn,2H), 7.70(t,2H), 7.925(m,3H). 183 8 1.78(m,4H), 2.21(s,3H), 2.75(d.4H), 3.43(s,3H), 3.92(s,3H), 5.26(£.2H), 7.01(m,lH), 7.20(m,lH), 7.32(m,5H), 7.52(m,lH). 189 87.63(m,3H), 7.40(m,5H), 7.20(m,lH), 5.12(AB q, 2H), 3.94(d,3H), 3.875(s,3H), 3.41(s,3H). 190 8 7.75(m,lH), 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,lH), 7.6-7.9(m,lH), 7.6(s,lH), 7.4-7.6(m,5H), 7.2-7.3(lH), 5.3(m,lH), 3.7-3.9(d,3H), 3.45(m,3H), 1.6(m,3H). 193 5 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 8 3.38(s.3H), 3.83(s,3H), 6.7-6.8(m.3H), 7.0-7.l(m,3H). 7.1-7.2(m,3H). 7.3-7,4(m,4H). 198 8 7.94(t,lH), 7.66(m,lH), 7.54(m,2H), 7.43(m,2H), 7.23(d,lH), 7.06(t,lH), 5.24(q,2H), 3.88(s,3H), 3.41(s,3H), 2.14(s.3H). 199 8 7.55(m,lH), 7.51(m,2H), 7.46(m,2H), 7.25(m,lH), 5.14(q,2H), 4.08(s,3H), 3.915(s,3H), 3.435(s,3H). 200 8 7.92(s,lH), 7.85(d,lH), 7.60(m,2H), 7.45(m,3H), 7.24(m,lH), 5.14(q,2H), 4.03(s,3H), 3.88(s.3H). 3.41(s,3H). 201 8 7.2-7.5(m,4H), 6.9-7.3(1,1 H), 3.42(s,3H), 2.22(s,3H). 203 8 7.55(m,5H), 7.25(d,lH), 5.12(q,2H), 4.07(s,3H), 3.53(s,3H). 204 8 7.85(s, IH), 7.75(d,lH), 7.4-7.7(m,5H), 7.3(d,lH), 7.05(t,lH), 5.23(m,2H), 3.34(s.3H), 2.19(s.3H). WO 97/00612 PCT/US96/10326 159 205 57.45-7.65(m,5H), 7.33(s.lH). 7.26(d.lH). 5. l-5.4(m.2H), 3.5(s.3H). 2.13(s,3H). 207 57 60(d.lH). 7.50-7.30(m,4H), 7.25(m.2H), 5.23(d.lH), 5.20(d.lH). 3.89(s.3H), 3.41(s.3H), 2.1S(s.3H), 1.68(s.4H), 1.26{m.l2H). 209 57.58(m,lH), 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 EH mixture) 5 7.66 and 7.21 (2s,IH 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 5 8.18(s,lH), 7.98(m,lH), 7.82(m,lH), 7.50(m,4H). 7.Z0(d,lH). 5.59(d,lH), 5.46(d,lH), 3.39(s,3H), 3.41(s,3H). 212 5 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 87.68(d.lH), 7.6(m,lH), 7.48(m,4H), 7.28(m,lH), 5.41(AB q,2H), 3.91(s,3H), 3.38(s,3H), 3.20(s,3H). 215 57.6(d,lH), 7.3-7.5(m,4H), 7.2(d,lH), 6.95(s.lH), 6.9(d,lH), 4.27(s,2H). 3.86(s,3H), 3.41(s,3H), 1.95(s,3H). 217 57.65(d,lH), 7.6-7.1 (m,6H), 5.15(m,2H), 3.95(m,lH), 3.45(s,3H), 2.6(d,3H), 2.2(s,3H), 1.65(s,4H). 1.25(s,12H). 220 83.6(s,3H), 6.8(m.3H), 7.0-7.)(m,3H), 7.1-7.2(m.2H). 7.3(m,lH), 7.35(m,3H), 7.45(m.lH). 221 [in Me2SO-46): 5 1.95(s,3H), 2.0(s,3H). 3.75(d.2H). 3.85(s,3H), 6.55(m,2H), 7.05(m.lH), 7.4-7.5(m,3H), 9.05(s.lH). 222 S7.76(s,lH), 7.60(m,lH), 7.54(m,lH), 7.36(d,lH), 7.32(d,lH), 6.94(d,lH), 5.29(s,2H), 3.89(s.3H). 3.41(s,3H), 2.21(s,3H), 0.28(s,9H). 231 57.67(m,lH), 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 8.68(d,lH), 7.80(s,IH), 7.75(d,lH), 7.60(m,2H), 7.43(m,2H), 5.54(d,lH), 5.40(d,lH), 3.82(s,3H), 3.35(s.3H), 2.17(s,3H). 237 57.84(s,lH), 7.77(d,J=8Hz, IH), 7.58(m,2H). 7.45(m,3H), 7.26(m,lH), 5.31(d,J=13Hz, IH), 5.22(d,J=13Hz, IH), 3.89(s,3H), 3.81(m,2H), 2.21 (s,3H), 1.33(t,J=7Hz, 3H). 238 5 1.6-1.8 (m,13H), 2.0-2.1 (m,5H), 3.44 (s,3H), 3.94 (s,3H), 5.09 (s,2H), 7.32 (m.3H), 7.48 (m,lH). 240 5 7.39 (m,lH), 7.33 (d,2H), 7.26 (m.lH), 6.99 (m,2H). 6.88 (m.2H), 5.01 (s,2H), 3.84 (s,3H), 3.81 (s.3H), 3.41 (s,3H). WO 97/00612 PCT/US96/10326 160 243 5 7.43 (m.3H). 7.2S <m,lH), 7.22 (m.2H), 7.15 (m.lH). 7.04 (m.lH), 5.12 (q,2H) 4.5 1 (s,2H), 3.89 (s.3H), 3.43 (s,3H). 1.91 (s.3H). 244 5 7.45 (m,3H), 7.23 (m, 1H). 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 5 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 5 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 5 7.44 (m,3H), 7.23 (m,lH). 6.96 (m.lH), 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 5 7.6 (d.lH), 7.15-7.5 (m,5H), 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 57.45 (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 8 7.56 (m,3H), 7.45 (m,2H), 7.35 (t,lH), 7.25 (m.lH). 5.12 (q,2H), 4.01 (s.3H), 3.89 (s,3H), 3.43 (s,3H). 255 5 3.47 (s,3H), 3.77 (s,3H), 6.61 (m,2H), 6.70 (m, 1H), 7.01 (dd,lH,J= 1.2.8.2), 7.2-7.3 (m,2H), 7.34-7.42 (m,2H). 2.59 6 1.80 (d,6H), 3.52 (s,3H), 5.01 (q,2H), 7.26 (m.lH). 7.52 (m,3H). 262 8 7.85 (d,lH), 7.8 (m,lH), 7.55 (d.lH), 7.45 (m,2H), 7.25 (IH), 7.2 (t,lH), 5.25 (m,2H), 3.9 (s,3H), 3.4 (s,3H), 2.19 (s,3H). 265 5 7.84 (m,3H), 7.64 (d,2HV 7.6-7.55 (m.lH), 7.5-7.4 (m,2H), 3.88 (s,3H), 3.43 (s,3H). 273 5 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 53.38 (s,3H), 3.85 (s,3H), 6.7-6.9 (m,3H), 6.95 (m,lH), 7.1 (m.lH), 7.2-7.4 (m,5H), 7.5 (m.lH), 7.6 (m.lH). 276 8 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,5H), 7.54 (m,lH), 7.95 (dd,lH,J= 1.7.8.0). 277 5 3.39 (s,3H). 3.85 (s,3H), 6.87 (t.lH). J=2.2), 6.92-6.96 (m,2H), 7.08 (d.lH, J=8.2), 7.17-7.26 (m,2H), 7.3-7.4 (m,3H), 8.3-8.4 (m,2H). 281 5 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 87.78 (s,2H), 7.625 (s,lH), 7,42 (m,3H), 7.23 (m,lH), 5.03 (q,2H), 3.92 (d,3H), 3.67 (s.2H), 3.42 (s.3H), 1.905 (s,3H). 283 8 7.45 (m,4H), 7.33 (s.2H), 7.24 (m, 1H), 5.12 (q.2H), 4.57 (s.2H). 3.91 WO 97/00612 PCT/US96/10326 161 (s.3H). 3.43 (s.3H). 1.925 (s.3H). 298 5 8.0(m,lH), 7.88 (m,lH), 7.625 (m.lH), 7.48 (m,4H), 7.25 (m.lH). 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. 259 5 7.85 (m.lH), 7.75 (m.lH). 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 8 3.41 (s.3H), 3.88 (s.3H), 4.02 (s,3H). 5.17 (AB q,2H), 7.25 (m.lH), 7.46 (m,4H), 7.64 (m,lH), 7.8 (m,4H), 8.12 (s.lH). 301 5 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.3H). 8.21 (dd.lH,J=2.3,7.1). 305 5 7.37 (m.2H), 7.26 (m,3H), 7.02 (m,3H), 3.86 (s,3H), 3 37 (s,3H). 307 8 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 b 7.41 (m,3H), 7.21 (m,3H). 7.14 (m.lH), 5.06 (q.2H). 3.9 (s.3H), 3.58 (s,2H), 3.43 (s,3H). 1.89 (s,3H). 311 5 8.18 (m.2H), 7.65 (m.lH), 7.55 (t,lH), 7.49 (s,2H), 7.13 (t,2H), 3.78 (s,3H). 3.36 (s,3H). 314 5 3.39 (s,3H). 3.85 (s,3H), 6.8-7.0 (m,4H), 7.0-7.1 (m,2H), 7.2 (m,lH), 7.3-7.4 (m,3H), 7.69 (m,lH), 8.19 (dd,lH,J=1.8,5.0). 315 8 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 5 2.38 (s.3H), 3.36 (s,3H), 3.79 (s,3H). 6.35 (d,lH,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 5 8.08 (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 8 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-rf6]: 8 7.92-7.45 (m,8H), 3.79 (s.3H), 3.25 (s,3H). 339 8 2.88 (s,3H), 3.37 (s,3H), 3.79 (s,3H), 6.35 (d, 1 H,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 8 8.22 (d,2H), 7.61-7.48 (m,4H), 7.28 (m.2H), 3.78 (s,3H). 3.36 (s,3H). 344 8 8.19 (d,2H), 7.65-7.50 (m.2H), 7.49 (s.2H), 7.17 (d,2H), 6.57 (t.lH), 3.78 (s,3H), 3.36 (s,3H) 346 8 7.86 (d.lH). 7.77 (m.lH). 7.55 (m.lH), 7.44 (m,2H), 7.23 (d.lH), 6.95 WO 97/00612 PCT/US96/10326 162 (d.lH). 5.24 (q.2H). 4.44 (q,2H), 3.9 (s.3H), 3.4 (s,3H), 2.18 (s.3H). 347 5 7.79 (t,lH), 7.57 (d,2H), 7.5 (m,3H), 7.23 (m,2H). 5.12 (AB q,2H), 3.9S (s.3H), 3.88 (s.3H), 3.42 (s,3H). 352 5 2.22 (s,3H), 3.38 (s,3H), 3.82 (s.3H). 6.60-6.66 (m,3H), 6.97 (m.lH). 7.0-7.1 (m,2H), 7.1-7.3 (m,4H), 7.4-7.5 (m,2H). 353 57.53 (m,2H). 7.45 (m,2H), 3.81 (s.3H), 3.40 (s,3H), 2.15 (m.lH), 1.0 (m,4H). 354 5 7.56 (m.lH). 7.50 (m.lH), 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), 1.70 (br m,2H). 355 [in C6D6]: 5 7.7 (d.2H), 7.2 (d,2H), 6.85 (m,4H), 6.6 (d,lH), 6.2 (d.lH). 5.35 (d,lH), 4.75 (d.lH), 3.10 (s. 3H). 356 5 8.09 (d,2H), 7.65 (d.lH), 7.55 (m.lH), 7.5-7.35 (m,4H). 3.70 (s,3H), 3.24 (s,3H). 357 57.49 (s,lH), 7.4 (m,lH), 7.3 (d,lH),7.1 (m,2H),5.l9 (dd,2H). 3.90 (s,3H), 3.44 (s.3H). 360 5 8.2 (s.lH), 7.95 (d.lH). 7.8 (d.lH), 7.6 (d,lH), 7.45 (m.3H), 7.25 (IH), 5.25 (m,2H), 3.89 (s.3H), 3.41 (s.3H),2.22 (s.3H), 1.6 (s.9H). 363 5 8.1 (d,lH), 8.0 (s,lH), 7.75-7.6 (m,2H), 7.55-7.4 (m.3H), 7.3 (m,lH), 3.45 (s.3H). 364 5 8.24 (s,lH), 8.0 (d.lH), 7.65 (m,2H), 7.5 (m,3H), 3.45 (s,3H). 367 5 8.26 (d.2H), 7.75-7.6 (m,4H), 7.55-7.45 (m,2H), 3.45 (s,3H). 368 5 8.06 (d,2H), 7.75 (d,lH), 7.7-7.6 (m,lH), 7.5-7.4 (m, 4H), 3.46 (s,3H), 1.34 (s,9H). 369 57.71 (d.lH), 7.65-7.55 (m.lH), 7.5-7.4 (m,2H), 3.49 (s,3H), 1.35 (s,9H). 370 53.34 (s.3H). 3.76 (s,3H), 6.49 (d,lH,J=7.9), 6.53 <d,lH,J=7.9), 7.1-7.2 (m,3H), 7.2-7.4 (m,6H), 7.64 (t,lH,J=8.0). 372 5 3.40 (s,3H), 3.74 (s,3H), 3.84 (s,3H). 6.5-6.6 (m,2H), 6.7 (m, 1H), 6.95 (m,lH), 7.2-7.3 (m,2H), 7.3-7.4 (m.2H). 7.6-7.7 (m,lH), 8.07 (dd,IH,J=1.8, 8.1), 8.15 (dd,lH,J=1.7,7.8). 373 57.93 (m,3H), 7.56 (m,lH), 7.43 (m,2H), 7.25 (m.lH), 5.3 (q,2H), 3.89 (s,3H), 3.4 (s,3H), 2.15 (s,3H). 374 57.5 (d.lH), 7.4 (m,4H), 7.2 (d, IH), 7.1 (d,2H), 5.1 (q,2H), 3.888 (s.3H). 3.4 (m,5H), 1.715 (s,3H), 0.252 (s,10H). 375 5 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 5 3.4 (s,3H), 3.8 (s,3H), 7.2-7.6 (m,6H), 7.8 (d,lH), 8.0 (s,lH). WO 97/00612 PCT/US96/10326 163 384 5 3.34 (s.3H). 3.82 (s,3H). 7.05 (m.l H), 7.21 (m.2H). 7.36-7.50 (m,5H), 7.71 (d.lH), 7.81 (d,2H). 386 5 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,lH,J=1.3,8.3), 7.14 (d.2H.J=S.2), 7.2-7.3lm.2H). 7.3-7.4 (m,2H). 387 8 3.39 (s,3H), 3.82 (s,3H), 3.S3 (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.IH), 7.91 (dd,lH,J=1.8,7.8) 389 8 2.05 (s.3H), 3.39 (s,3H). 3.S3 (s.3H), 6.7-6.8 (m.3H), 6.8-6.9 (m.2H), 6.95 (m.IH), 7.0 (m.IH), 7.2-7.3 (m.3H), 7.3-7.4 (m.2H). 390 8 8.15 (s.lH), 8.05 (m.IH), 7.65 (d,lH), 7.55 (t.lH), 7.46 (m,4H), 3.70 (s.3H), 3.24 (s„3H). 391 8 7.80 (s.lH), 7.65 (d.lH). 7.45 (m,2H), 7.35 (m.2H), 7.30-7.20 (m,3H). 6.53 (s.lH), 5.50 (d.lH). 5.35 (d.lH), 3.80 (s,3H), 3.43 (s,3H). 392 8 7.67 (d,2H), 7.62 (d.lH), 7.60-7.35 (m,4H), 3.77 (s,3H). 3.35 (s.3H). 393 8 7.55 (m,2H), 7.45 (m,2H), 3.89 (s,3H), 3.42 (s,3H), 3.40 (s,3H). 394 8 7.63 (d,2H). 7.5 (m.IH), 7.43 (m,lH), 3.5 (s,3H), 3.42 (s,3H). 395 8 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.lH). 397 8 3.4 (s.3H). 3.9 (s.3H), 7.38-7.5 (m,7H), 8.2 (IH), 7.61 (d,lH). 400 87.93 (t,lH), 7.845 (t,lH), 7.77 (t,lH). 7.57 (m.IH), 7.45 (m,2H), 7.25 (m.IH), 5.12 (q,2H). .40 (s,3H), 3.9 (s,3H), 3.43 (s,3H). 401 87.74 (s.lH), 7.6 (m,2H), 7.45 (m,2H), 7.31 (d.lH), 7.2 (m.IH), 5.13 (AB q,2H), 4.06 (s,3H), 3.90 (s,3H), 3.42 (s,3H). 402 8 7.85 (IH), 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 8 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 8 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 8 2.14 (s,3H), 3.35 (s,3H), 3.75 (s,3H), 6.40 (d,lH,J=8.0). 6.48 (d,lH,J=8.0), 7.03 (m.l H). 7.1-7.3 (m.SH). 7.3-7.4 (m.2H). 7.59 (m, 1H). WO 97/00612 PCT/US96/10326 164 418 5 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 5 3.38 (s,3H), 3.86 (s,3H). 6.S-6.9 (m.2H), 7.0-7.1 (m.2H), 7.15 (m.IH), 7.2-7.3 (m.IH), 7.4-7.5 (m,3H). 8.35 (m.IH), 8.6 (m.IH). 420 5 3.39 (s,3H), 3.82 (s,3H), 3.S3 (s,3H), 6.6-6,7 (m,3H), 6.9-7.0 (m,l H). 7.0 (m.3H), 7.1-7.2 (m.3H), 7.3-7.4 (m,2H). 421 5 3.39 (s,3H), 3.82 (s,3H). 3.93 (s.3H), 6.46 (d,lH.J=7.8), 6.66 (d,lH,J=7.7), 6.9-7.0 (m,3H), 7.1-7.3 (m.4H), 7.4 (m,2H). 422 5 3.39 (s,3H). 3.85 (s,3H), 6.68 (d,lH,J=6.5), 6.85-6.95 (m,3H), 7.04 (dd,lH.J=1.2,8.3), 7.25 (m.IH). 7.30-7.45 (m,4H). 423 6 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, 1H). 7.66 (m, 1H). 424 8 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 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 8 3.4 (s,3H), 3.89 (s,3H), 7.3-7.6 (m,6H). 7.65 (d, IH). 7.8 (3,1H). 430 8 7.65 (d,lH), 7.05-7.6 (m,l IH), 6.9 (d,lH), 5.15 (m,2H), 3.89 (s,3H), 3.38 (s,3H). 442 8 7.82 (t.lH), 7.64 (itj,3H), 7.44 (m,3H), 7.25 (m.IH), 6.71 (s.lH), 5.13 (q,2H), 4.0 (s,3H), 3.88 (s,3H), 3.41 (s,3H). 447 8 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,5H), 7.62 (dd,lH,J=l.6,7.8). 448 8 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.IH), 7.05 (m.IH). 7.1-7.3 (m.5H), 7.38 (m.2H). 449 8 7.55 (m,2H), 7.47 (m.2H), 3.86 (s,3H), 3.39 (s,3H). 452 8 8.05 (s.lH). 7.65 (d.lH), 7.60 (m.IH), 7.55 (m.IH), 7.45 (m,2H), 7.35 (m.IH), 3.78 (s,3H), 3.36 (s.3H). 453 8 7.75 (s.lH), 7.60 (d.lH). 7.55 (m,lH). 7.45 (m,2H), 7.40 (d,lH), 7.10 (m.IH), 3.79 (s,3H), 3.38 (s.3H). 454 8 3.4 (s,3H), 3.87 (s,3H), 7.3-7.6 (m,13H). 455 8 3.4 (s.3H), 3.9 (s,3H), 7.4-7.6 (m,4H), 8.0 (s,lH), 8.3 (s,2H). 462 8 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 8 3.408 (s,3H), 3.89 (s,3H). 7.4-7.6 (m,3H), 7.7 (d,lH), 7.9 (d.lH). WO 97/00612 FCT/US96/10326 165 467 5 8.2 (s.lH), 8.1 (d. IH), 7.6 (d. 1H). 7.35-7.55 (m.5H), 3.84 (s,3H). 3.40 (s,3H). 468 5 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.l H). 469 5 3.38 (s,3H). 3.86 (s,3H), 6.68 (d.lH,J=S.5), 6.80 (m,l H). 6.82-6.91 (m.3H), 7.07 (dd,lH,J=1.0,8.2), 7.2(m,lH), 7.3-7.5 (m,4H). 470 5 3.40 (s,3H). 3.83 (s,3H), 6.66 (m,2H), 6.76 (m,lH), 7.04 (d,lH,J=S.2), 7.2-7.5 (m,7H). 471 5 3.40 (s,3H), 3.83 (s,3H), 6.6 (m.IH), 6.65 (m.IH), 6.80 (m.IH), 7.00 (m.IH), 7.2-7.3 (m.2H),7.35-7.40 (m,2H), 7.55-7.60 (m.IH), 8.19 (d,2H,J=8.2). 472 5 3.38 (s,3H). 3.84 (s,3H), 6.7-6.9 (m.5H), 7.0-7.5 (m,6H). 473 5 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.IH), 6.89 (d,lH,J=7.8), 7.02 (m.IH, 7.1 (m.IH), 7.2-7.3 (m,2H), 7.3-7.4 (m,2H). 479 5 7.57 (m,2H), 7.44 (m.2H), 7.24 (m,2H). 7.05 (d.lH), 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 6 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 5 7.5 (m,4H), 7.2(m.2H), 7.03 (d.lH), 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 5 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 5 7.55 (d, 1H), 7.45 (m,2H), 7.2-7.35 (m.4H), 6.95 (d,IH), 5.25 (m,2H), 4.4 (m,2H), 3.88 (s,3H), 3.40 (s,3H), 2.18 (s,3H). 485 5 7.6-7.45 (m,5H), 3.82 (s,3H), 3.38 (s,3H). 490 6 8.35 (s.lH), 8.15 (d.lH), 7.7-7.4 (m.8H), 7.36 (m,3H). 3.78 (s,3H), 3.37 (s,3H). 492 6 8.15 (s.lH), 8.00 (d,lH), 7.65-7.30 (m.6H), 4.24 (q,2H), 3.76 (s,3H), 3.37 (s,3H), 1.48 (t,3H). 493 5 8.35 (s.lH), 8.15 (d.lH). 7.7-7.4 (m,7H), 7.09 (m,3H). 3.79 (s,3H), 3.38 (s.3H). 494 5 8.65 (d.lH). 8.40 (s,lH), 8.20 (d.lH), 7.75-7.4 (m.9H), 3.78 (s.3H), 3.38 (s,3H). 495 5 8.25 (s,lH), 8.10 (d,lH). 7.65-7.45 (m,5H), 7.40 (t.lH), 4.9 (m.IH), 4.51 (m,2H), 3,90 (m,lH). 3.77 (s.3H), 3.60 (m.IH), 3.37 (s,3H), WO 97/00612 497 4 £>9 503 504 505 506 508 515 526 527 528 530 531 532 533 534 535 536 537 PCT7US96/10326 166 1.90- i.55 (m,6H). 5 10.09 (s.IH), 8.66 (s.IH). 8.45 (d.IH), 8.0 (d.IH), 7.7-7.55 (m,3H) 7.5 (m,2H). 3.80 (s,3H). 3.36 (s.3H). 8 3.38 (s,3H), 3.86 (s.3H), 6.75 (s.IH), 6.75-6.83 (m,2H). 6.88 (d,2H.J=1.7), 7.05 (m,2H), 7.09 (t,lH.J=1.7), 7.2-7.4 (m.3H). 8 3.38 (s,3H), 3.84 (s,3H). 6.7-6.8 (m.3H), 7.04 (dd,lH,J=l .1. 8.2), 7.19-7.45 (m,9H). 8 3.38 (s.3H). 3.84 (s,3H), 6.70 (m,2H), 6.75-6.83 (m,4H), 7.04 (dd.lH,J=l.0.8.2), 7.2-7.3 (m.3H), 7.35-7.40 (m,2H). 8 3.38 (s.3H), 3.84 (s,3H), 6.7-6.8 (m.3H), 6.8-6.9 (m.IH), 6.9-7.1 (m,3H), 7.2-7.3 (m,2H). 7.35-7.40 (m,2H). 8 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). 8 8.9 (s.IH), 8.4 (d.IH), 7.65 (d.IH), 7.55 (m,lH), 7.49 (m.2H). 6.9 (d.IH), 4.82 (q,2H), 3.80 (s,3H). 3.37 (s,3H). 8 7.85 (s.IH), 7.8 (d.IH), 7.3-7.6 (m.6H). 3.85 (s.3H). 3.40 (s,3H), 2.49 (s.3H). 8 7.57 (m,2H), 7.49 (rn.2H). 7.02 (d.IH), 6.45 (d.IH), 3.80 (s,3H), 3.37 (s,3H) 8 8.21 (d,2H), 8.1 (d,2H), 7.7-7.4 (m,9H). 3.77 (s,3H), 3.37 (s.3H) 8 7.7 (d.IH), 7.6-7.4 (m,5H), 7.25 (m.IH), 6.9 (dd.lH). 6.75 (s.IH), 3.80 (s,3H), 3.34 (s.3H). 8 7.55 (m,2H), 7.45 (m,2H), 3.83 (s.3H), 3.39 (s,3H), 1.32 (s,9H). 8 7.75 (d.IH), 7.7-7.4 (m.5H), 7.3 (m.IH), 6.95 (dd.lH), 3.77 (s,3H). 3-38 (s,3H), 1.00 (t.9H). 0.76 (q,6H). 5 7.75 (d.IH). 7.65 (m,2H). 7.6-7.45 (m.3H), 7.3 (m.IH), 6.9 (m.IH), 3.77 (s.3H). 3.38 (s,3H), 1.00 (s.9H). 0.22 (s,6H). 8 8.1 (d.IH), 8.05 (s.IH), 7.65-7.55 (m,2H), 7.5-7.45 (m,3H), 7.3 (dd.lH), 4.88 (s,2H), 3.78 (s,3H). 3.37 (s,3H). 8 8.1 (d.IH), 8.0 (s.IH), 7.65-7.45 (m.5H), 7.3 (m.IH), 6.5 (q.lH), 3.78 (s.3H), 3.37 (s.3H), 1.92 (d,3H). 8 8.1 (d.IH), 8.0 (s.IH), 7.65-7.55 (m.2H), 7.5-7.45 (m,3H), 7.3 (m.IH), 7.15 (dd.lH). 5.05 (dd.lH), 4.7 (dd.lH), 3.78 (s,3H), 3.37 (s,3H). 8 8.05 (d.IH), 7.95 (s.IH). 7.65-7.4 (m,5H). 7.15 (dd.lH). 3.77 (s,3H), 3-37 (s,3H), 1.37 (s,9H). 8 7.95 (d.IH). 7.7-7.3 (m,6H). 7.15 (dd.lH), 5.28 (s,2H), 3.8 (s.2H), 3.77 WO 97/00612 PCT/US96/10326 167 (s,3H). 3.38 (s,3H), 0.95 (m.2H). 0.0 (s,9H). 538 5 8.2 (d.IH), 8.1 (s.IH), 7.65-7.45 (m,5H), 7.35 (dd.lH). 3.80 (s,3H), 3.37 (s,3H). 539 5 7.64 (d.IH), 7.55 (m,lH). 7.47 (m.3H), 3.80 (s.3H), 3.39 (s,3H). 540 5 7.54 (m.2H), 7.46 (m,2H), 7.33 (s.IH), 7.24 (m.3H), 4.09 (s.2H), 3.73 (s,3H). 3.39 (s,3H). 541 8 7.53 (m,2H), 7.46 (m,2F), 7.27 (s,4H), 4.08 (s,2H), 3.73 (s,3H). 3.38 (s,3H). 547 [in C6D6]: 8 8.15 (s.IH), 8.1 (d.IH), 7.15 (m.IH), 7.1 (t.lH), 7.05 (m,lH), 6.9 (dd.lH), 6.8 (m,2H). 3.25 (s,3H), 3.0 (s,3H), 0.15 (s,9H). 548 5 7.75 (d,lH), 7.7 (s.IH), 7.65 (s.IH), 7.55 (m.IH), 7.5 (m,2H). 7.35 (t.lH), 7.0 (d.IH). 6.15-6.0 (m.IH), 5. 45 (d.IH), 5.3 (d,5H), 4.6 (d,2H), 3.77 (s,3H), 3.37 (s,3H). 549 8 7.8 (d.IH), 7.75 (s.IH), 7.65 (s.IH), 7.55 (m.IH), 7.5 (m,2H), 7.35 ft.lH), 7.05 (dd.lH). 6.05 (s.IH), 5. 7 (s,lH), 4.7 (s.2H), 3.78 (s,3H), 3.37 (s,3H). 553 8 7.3-7.5 (m,3H), 7.2 (s.IH), 4.4-4.7 (q,2H), 3.861 (s,3H), 3.6 (q,2H). 3.384 (s,3H). 554 8 7.65 (s,2H), 7.35-7.6 (m,4H), 7.3 (IH), 7.1 (IH). 3.8 (s,3H), 3.4 (s.3H). 556 8 8.21 (s.IH), 8.05 (d.IH), 7.65 (d.IH), 7.55 (m,lH), 7.5 (m,3H), 7.4 (m.IH), 6.8 (dd.lH), 5. 85 (d.IH), 5.3 (d.IH), 3.77 (s,3H), 3.37 (s,3H). 562 5 8.2 (s.IH). 8.1 (d.IH), 7.35-7.65 (m.6H), 3.84 (s,3H), 3.40 (s,3H). 563 [in Me2SO-<f6]: 8 7.75 (d.IH), 7.65 (m,2H), 7.55 (t,lH), 3.80 (s,3H), 3.5 (m,4H), 3.27 (s,3H), 1.15 (m,6H). 564 8 7.85 (s.IH), 7.75 (d.IH), 7.3-7.6 (m,6H). 3.84 (s,3H), 3.40 (s,3H), 2.9 (m,2H), 1.3 (t,3H). 566 8 8.82(d,J=5Hz.lH), 7.95 (s.IH), 7.61 (m.IH). 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 5 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 8 7.55 (m,2H), 7.46 (m,2H), 3.86 (s.3H), 3.40 (s,3H). 570 8 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 8 7.55 (d.IH), 7.39 (m,4H), 7.2 (m.IH), 7.08 (IH). 6.99 (d.IH). 4.34 WO 97/00612 PCT/US96/10326 16S (m,2H), 3.84 (S.3H), 3.42 (s,3H), 2.46 (s,3H). 572 58.25 (m.lH), 8.15 (d.IH), 7.65-7.45 (m,6H). 7.39 (t.lH), 3.7K (s.3H), 3.37 (s,3H). 573 5 7.65 (d.IH), 7.55 (m,lH). 7.49 (m,4H). 6.85 (m,l H), 5.26 (s,4H). 3.77 (m,7H), 3.39 (s.3H), 1.0 (m,4H), 0.00 (s,18H). 575 5 7.78 (distorted d, IH). 7.57-7.50 (m,2H), 7.45-7.40 (m,2H), 7.30-7.28 (m.IH), 7.04 (s.IH), 6.83-6.80 (m.IH), 3.95 (apparent d, 3H), 1.28 (S.9H). 576 5 7.6 (d.IH), 7.45 (m,4H), 7.4 (s,lH), 7.25 (rn,2H), 5.0 (m,2K), 3.91 (s,3H), 3.41 (s.3H). 2.24 (s.3H). 577 S 7.55 (m,2H), 7.5 (m.2H). 7.45 (d,2H), 6.67 (t.lH), 4.43 (q,4H). 3.81 (s,3H), 3.33 (s,3H). 580 5 7.55 (s.IH), 7.4 (m,4H), 7.2 (m.IH), 6.7 (m,2H), 4.33 (m,2H), 3.86 (s,3H), 3.43 (s.3H), 2.44 (s,3K). 581 57.53 (d.IH), 7.4 (m,2H), 7.2 (m.IH), 7.06 (m.IH), 6.71 (d,2H), 4.32 (q,2H), 3.875 (s,3H), 3.44 (s,3H). 2.46 (s,3H). 589 major component: 5 7.33 (d.IH), 6.95 (d.IH), 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 (a), 7.49 (t); minor component: 5 6.62 (s.IH), 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 5 8.69 (m.IH), 7.94 (s.IH), 7.85-7.73 (m,4H), 7.61 (d.IH), 7.59-7.45 (m,2H), 7.38 (dd.lH), 5.50 (AB pattern. 2H), 3.78 (s,3H), 3.35 (s,3H), 2.25 (s,3H). 613 5 7.70 (s.IH), 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 57.86 (s.IH), 7.76 (d.IH), 7.64 (d.IH), 7.59 (d.IH), 7.54 (d,lH), 7.53-7.47 (m,lH), 5.01 (br s,2H), 4.96 (s,2H), 3.89 (s,3H). 3.33 (s,3H). 645 5 7.65 (d.IH), 7.6 (s.IH), 7.4-7.55 (m,4H), 7.35 (t.lH), 7.25 (d,lH), 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 5 7.6 (d.IH), 7.4-7.55 (m.5H), 7.35 (m,2H). 5.24 (s.2H), 3.54 (s.3H). 2.15 (s,3H). 650 6 7.65 (m.2H), 7.55 (s,2H), 7.5 (m,2H). 7.25 (IH), 5.2 (m.2H), 4.1 (m.IH), 3.43 (s,3H), 2.55 (d,3H), 2.24. (s,3H), 0.25 (s,18H). 652 5 7.2-7.7 (m,8H), 5.3 (d,2H). 3.4 (s.3H). 2.6 (s,6H), 2.2 (s.3H), 0.3 W0 97/00612 PCT/US96/10326 169 (s.9H). 653 5 7.85 (s.IH), 7.75 (d.IH). 7.6 (m,2H). 7.45 (m.3H), 7.2 (d. IH). 5.2 (m.2H). 3.5 (s.3H), 2.2 (s,3H), 2.0 (s,3H). 654 5 7.45 (s.IH), 7.25-7.4 (m,3H), 7.2 (d.IH), 3,55 (s,3H), 2.28 (s,3H). 655 5 7.25-7.4 (m.3H), 7.15 (d.IH), 3.5 (s,3H). 2.3 (m.2H). 2.2 (s,3H), 1.1 (t.3H). 656 5 8.1 (d.IH), 8.0 (s.IH). 7.65-7.4 (m,4H), 7.3 (m.IH). 3.79 (s.3H), 3.36 (s.3H). 658 5 8.03 (s.2H), 7.55 (s,2H), 7.5 (s.IH), 7.45 (s.IH). 3.81 (s.3H), 3.35 (s,3H). 659 5 8.61 (s.2H), 7.95 (s.IH), 7.56 (m,2H), 7.5 (m.IH), 3.82 (s,3H), 3.35 (s.3H). 661 5 8.25 (d.2H), 7.69 (d.2H), 7.59 (d.IH), 7.55-7.5 (m.2H), 3.79 (s.3H). 3.35 (s,3H). 663 5 7.55 (d.IH), 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.IH), 7.53 (d,2H), 7.5-7.35 (m,2H), 3.77 (s,3H), 3.30 (s,3H). 665 5 8.2 (s.IH), 7.95 (d.IH), 7,65 (d,lH), 7.5-7.35 (m.3H), 3.79 (s,3H), 3.31 (s.3H). 667 5 8.05 (d.IH), 7.95 (s.IH), 7.65 (d.IH), 7.5-7.35 (m,3H). 7.3 (d.IH), 3.77 (s,3H), 3.45 (s,3H). 668 5 7.6 (dd.lH), 7.5 (m,2H), 3.81 (s,3H), 3.36 (s,3H), 1.30 (s,9H). 670 5 8.58 (s,2H), 7.95 (s.IH), 7.65 (d,lH), 7.5-7.35 (m.2H), 3.80 (s,3H), 3.31 (s,3H). 671 5 8.04 (d,2H), 7.6 (dd.lH), 7.43 (d,4H), 3.75 (s,3H), 3.31 (s,3H). 1.32 (s.9H). 681 5 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,lH,J-8.2), 6.93 (d,lH.J=7.7). 7.05-7.10 (m,2H), 7.15-7.30 (m,4H). 682 5 2.26 (s.3H), 3.39 (s,3H), 3.82 (s,3H), 6.65 (m.IH), 6.70 (m,2H), 6.84 (d,lH,J=7.5), 7.0-7.1 (m,4H), 7.2-7.4 (m,4H). 683 5 2.26 (s,3H), 3.39 (s,3H). 3.83 (s,3H), 6.6-6.7 (m,3H), 6.84 (d. 1 H.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 5 2.26 (s,3H), 3.39 (s,3H), 3.82 (s,3H), 6.6-6.7 (m.3H), 6.84 (d,lH,J=7.7), 7.0-7.2 (m,5H). 7.25 (m.IH), 7.28 (m,lH). 688 5 2.26 (s,3H), 3.38 (s.3H), 3.84 (s,3H), 6.63 (t.lH.J=2.2), 6.68 (m,2H), WO 97/00612 PCT/US96/10326 170 6.83 (d.lH,J=8.0), 6.95-7.10 (m,5H). 7.2 (m.IH). 7.26 (m.IH). 689 5 2.26 (s,3H), 3.39 (s,3H). 3.81 (s.3H), 6.6-6.7 un.3H), 6.82 (m.IH), 6.95-7.05 (m,3H), 7.1-7.2 (m,2H), 7.2S (m.IH). 692 5 7.99 (s.2H). 7.50 (m.IH), 7.3S (m.2H). 3.82 (s.3H). 3.3S is.3H), 2.32 (s.3H). 700 57.35 (d,J=9.0Hz. 1H), 7.15 (d,J=2.7Hz, 1H), 6.93 (dd,J=9.0, 2.7 Hz.lH), 3.85 (s,3H), 3.78 (s.3H), 3.39 (s.3H). 1.37 s.9H). 707 5 2.28 (s,3H), 3.36 (s,3H), 3.91 (s.3H),.6.85 (m.IH), 6.9-7.0 (m.2H), 7.25 (m.IH), 7.3-7.4 (m,2H). 726 5 2.26 (s,3H), 3.39 (s,3H), 3.83 (s.3H), 6.6-6.7 (m,3H), 6.80-6.85 (m.IH), 7.0-7.1 (m,3H), 7.2-7.4 (m.3H), 7.61 (dd,lH,J=1.4,7.8). a *H 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 m)-broad multiplet, (AB q)-AB pattern quanet. Coupling constants (indicated by J) are in Hertz. 5 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 Trem® 014 (polyhydric alcohol esters). The 10 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. TESTA The test suspension was sprayed to the point of run-off on wheat seedlings. The 15 following day the seedlings were inoculated with a spore dust of Erysiphe graminis f. sp. tritici, (the causal agent of wheat powdery mildew) and incubated in a growth chamber at 20°C for 7 days, after which disease ratings were made. TEST B The test suspension was sprayed to the point of run-off on wheat seedlings. The 20 following day the seedlings were inoculated with a spore suspension of Puccinia recondita (the causal agent of wheat leaf rust) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 6 days, after which disease ratings were made. WO 97/00612 PCT/US96/10326 171 TEST C The test suspension was sprayed to the point of run-off on rice seedlings. The following day the seedlings were inoculated with a spore suspension of Pyricularia oryzae (the causal agent of rice blast) and incubated in a saturated atmosphere at 27°C 5 for 24 h. and then moved to a growth chamber at 30°C for 5 days, after which disease ratings were made. TEST D The test suspension was sprayed to the point of run-off on tomato seedlings. The following day the seedlings were inoculated with a spore suspension of Phytophthora 10 infesians (the causal agent of potato and tomato late blight) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 5 days, after which disease ratings were made. TESTE The test suspension was sprayed to the point of run-off on grape seedlings. The 15 following day the seedlings were inoculated with a spore suspension of Plasmopara viticola (the causal agent of grape downy mildew) and incubated in a saturated atmosphere at 20°C for 24 h, moved to a growth chamber at 20°C for 6 days, and then incubated in a saturated atmosphere at 20°C for 24 h, after which disease ratings were made. 20 TEST F The test suspension was sprayed to the point of run-off on cucumber seedlings. The following day the seedlings were inoculated with a spore suspension of Botrytis cinerea (the causal agent of gray mold on many crops) and incubated in a saturated atmosphere at 20°C for 48 h, and moved to a growth chamber at 20°C for 5 days, after 25 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 conuol 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. 30 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 44 WO 97/00612 PCT/US96/10326 264 91 97 265 35 93 266 0 93 267 0 97 268 35 97 269 100 99 270 61 97 271 61 97 272 61 93 273 77 85 279 60 84 280 100a 99a 287 100 100 288 99 100 289 99 100 290 99 100 291 99 100 292 100 100 293 100 100 294 99 99 295 99 100 296 100 100 297 55 65 306 99 85 309 100 100 310 99 99 311 312 73 85 317 86 85 320 99 97 321 100 99 322 99 93 323 99 100 324 99 99 325 100 99 326 99 100 86 94a 44 0 96a 3 86 46a 3 77 30a 44 77 48a 3 93 68a 44 77 69a 0 64 41a 3 93 82a 3 77 79a 3 63 70a 92 31b 94a 86 94a 44 76 99a 32 63 100a 0 86 100a 0 25 87a 0 86 63a 5 93 100a 68 76 100a 45 46 99a 82 93 100a 5 0 96a 45 0 5a 0 25 99a 0 63b 96a 0 25 99a 45 91 2a 0 100 91a 0 96 97a 0 91 78a 0 96 99a 42 91 86a 42 ND 100a 42 72b 97a 0 172 0 0 0 0 32 53 0 0 0 0 32 39a 86 74 53 53 97 53 86 91 74 86 53 32 97 74 53 0 86 100 53 53 53 86 86 WO 97/00612 PCT/US96/10326 173 327 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 0 333 95 93 53 96 94a 66 334 100 97 91 83 6!a 94 335 100 99 86 96 94a 3 337 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 94 345 100 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 0 361 100 97 53 22 48a 0 363 100 100 74 70 30a 0 364 99 97 74 53 23a 88 365 98 97 53 53 43a 0 366 99 97 53 82 15a 38 367 99 97 53 85 5a 81 36S 99 93 53 3 10a 88 369 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 - 0 394 0 86 0 20 - 0 395 100 100 91 20 - 7 396 99 99 0 97 67a 0 397 99 100 0 77 58a 0 405 89 86 0 57 26a 0 WO 97/00612 174 PCT/US96/10326 410 50 94 0 57 21a 0 411 50 99 0 91 Ila 0 412 93 94 53 0 19a 7 413 100 100 94 72 100b 0 425 61 94 0 60 lla 0 All 95 97 53 74 45a 0 428 36 94 74 74 2a 0 445 99 86 0 96 100b 1 446 100 100 53 84 45a 81 449 0 68 74 15 - 0 452 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 18a 92 457 100 93 73 91 89a 0 458 63 co 73 91 55a 0 459 100 93 93 91 100a 0 462 99 93 73 91 87a 0 465 0 85 0 0 23a 0 466 0 26 0 82 6a 0 467 100 100 90 NDb 100a 0 474 99 97 85 99 100a 0 475 100 99 85 91 100a 0 476 77 26 50 91 24 a 77 477 99 93 50a 91 I00a 0 478 98 100 97 92 82a 22 485 99 97 60 95 94 a 97 486 73a 48a 14b 13b 67a - 487 73a 70c 81b 32b 74a - 488 98 99 74 62 63 a 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 WO 97/00612 PCT/US96/10326 175 495 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 55 511 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 91a 85 519 60 93 51 16 - 0 520 100 100 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 lla 22 531 94d 97d 32d 65d - 99d 532 98 99 86 79 12a 99 533 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 - 98 538 100 100 91 95 100a 99 539 100 99 53 79 97a 94 540 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 I00a 99 a 59b _ 100a . WO 97/00612 PCTAJS96/10326 176 554 555 556 557 561 562 563 564 567 568 569 572 573 574 577 582 656 657 658 659 660 661 662 663 664 665 666 667 668 669 670 671 672 673 674 675 100a 100a 99 95 90 100 99 100 100 98 0 99 94 100 97 57 95 62 86 37 77 77 86 95 94 98 99 99 91 100 86 100 99 99 100 99a 99a 97 97 94 100 100 100 100 94 68 100 94 94 97 97 85 93 85 93 93 85 97 97 94 99 100 94 86 94 100 99 100 100 87b 88b 74 52 53 99 86 86 90 86 0 74 0 74 0 0 32 0 0 0 32 32 32 0 53 53 53 53 0 53 53 96 90 90 98 100 94 84 91 91 58 29 81 29 65 0 25 0 0 82 70 31 31 70 3 3 ND 61 43 20 20 20 20 60 85 ND 20 ND 98a 100a 72a 88a lla 100e 67a 3a 14a 97a 13a 16a 10a 44a 44 a 10a 29a 26a 37a 66b 35a 99a 100a 39a 94a 97 a 75a 100a 42 SI 98 0 0 0 0 47 0 0 0 0 0 79 38 38 38 79 38 79 0 46 7 7 0 82 7 67 0 0 60 0 0 bOOI £9 06 OOl OOl l£Z. 0 L bOS 0 06 66 OOl 0£Z. 0 bOOI 98 06 OOl 66 63 L 0 c 16 ZZ 06 OOl 66 83 L £8 b98 zz 06 66 66 LZL LP bOOI 9 L 16 66 OOl S3 L 0 cOOl - P6 OOl OOl PZL 0 b^8 91. 16 OOl OOl ZZL LP b ZL 9 L PL 66 OOl ZZ L zs sz ZZ P6 66 IZL LP bO S3 ZS P6 66 03 L 0 b6£ I 06 OOl OOl 6IL 0 bOOI ON 16 66 OOl L\L 0 bOOI - 16 66 66 9\L 0 PI P6 98 fr8 PIL P6 bf3 OOl 06 98 16 £1L 8fr kL6 8 L l£ Z.6 16 31L 0 • £9 0 Z.6 86 60 L 0 b6 L 91 35 £6 16 80 L 0 bOOI ON P6 OOl OOl 90 L - bc9 - ql L b66 b66 SO L 0 eOOI - 001 OOl OOl POL 0 bOOI ON 0 66 86 OOL 0 bOOI ON £6 OOl OOl 669 0 b^ OOl PL t-6 98 S69 Z6 b£9 £8 £8 P6 98 £69 0 bOOI OOl £8 66 16 £69 19 b96 OOl PL 66 66 369 Z.8 b6S ;6 09 P6 66 169 Z.Z. eOI 0 PL 66 66 069 19 b61 0 PL 98 56 S89 0 b98 Z9 L6 66 OOl 089 0 bOOI 16 £6 OOl OOl 6L9 0 cOOl ON 06 OOl OOl SL9 c cOOl 16 OOl 66 C16 LL9 0 gOOI - t-6 001 001 9L9 * LL t 9C€0l/96SfVX3d E1900/Z.6 OAA 9 WO 97/00612 PCT/US96/10326 178 a Compound was tested at 10 ppm (equivalent to 25 g/ha). l' 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). 5 Results for arthropodicide Tests G-L are given below for compounds of Formulae I, IA and IB. TEST G Fall Armvworm 10 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 15 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 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 insects were transferred from the 230-mL cup to the H.I.S. tray (one 20 insect per cell). The trays were covered and held at 27°C and 50% relative humidity for 48 hours, after which time readings were taken on the twelve cells with lima bean leaves. 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, 404,493, 538, 543, 546, 672, 673, 674, 677, 678, 679, 680, 688, 699, 701, and 703. 25 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 30 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, 35 345, 403, 404, 413, 442, 443, 445, 451, 479, 500, 506, 514,515, 537, 542, 546, 550, WO 97/00612 PCT/US96/10326 179 675, 677, 679, 680, 6S2, 6S3, 684, 6S7. 688, 6S9, 699, 700, 701, 703, 704, 705, 706, 715, and 717. * Tested at 0.55 kg/ha. TEST I 5 Aster Leafhopper Test units were prepared from a series of 350-mL (12-ounce) cups, each containing oat (Avena sativa) seedlings in a 2.5-cm (1-inch) layer of sterilized soil. The test units were sprayed as described in TEST G with individual solutions of the test compounds. After the oats had dried from the spraying, 10 to 15 adult aster leafhoppers 10 (Mascrosteles fascifrons) were aspirated into each of the cups. The cups were covered with vented lids and held at 27°C 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 15 Contact Test Against Black Bean Aphid Individual nasturtium leaves were infested with 10 to 15 aphids (all morphs and growth stages of Aphis fabae) 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 20 29-rriL (1-ounce) cup to prevent escape of the aphids that drop from the leaves. The test units were held at 27°C 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: 187,272, 28S, 304,321, 325, 329, 342, 343, 348,400, 413, 515, 538, 550, 554, 674, 679, and 688. 25 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 30 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 (?bout 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 35 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 27°C and 50% relative WO 97/00612 PCT/US96/10326 180 humidity for 48 hours, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 809b or higher: 146, 162, 187, 239, 247, 296, 306, 321, 325, 329, 343, 345, 373, 378, 467, 490, 493, 500, 515, 531, 532, 537, 538, 550, 670, 672, 673, 674, 675, 676, 677, 679, 680, 681, 683, 690, 693, 5 699, 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. 10 * 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 15 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 25°C 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. 20 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 O. The abbreviation "Ex." stands for "Example" and is followed by a number and step indicating in which example step the intermediate is 25 prepared. </div>

Claims

<div class="application article clearfix printTableText" id="claims"> 181 INDEX TABLE N ■v '•v tr N— N \ CH3 wherein R^3 is H or Cmpd No. X E£! m,p- (°Q 733 Ex. 1 Step C CI H solid* 734 Ex. 1 Step D CH3O H solid* 735 Ex. 22 Step D CH3O 6-CH3 194-196 736 Ex. 22 Step C CI 6-CH3 175-178 737 CH30 4-CH3O 163-165 738 CI 4-CH3O 192-194 ♦See Index Table O for *H NMR data. INDEX TABLE O Cmpd No. *H NMR Data (CDCI3 solution unless indicated otherwise)2 733 8 8.18 (s.IH), 7.11 (t,2H). 6.91 (t,»I), 6.76 (d.IH), 3.56 (s.3H). 734 8 8.40 (br s.IH), 7.20 (m,2H). 7.03 (d,lH), 6.94 (t,lH), 4.00 (s,3H), 3.48 (s,3H). a NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (m)-multiplet, (br s)-broad singlet. Where the terms "comprise", "comprises", "comprised" or "comprising" are used in this specification, they are to be interpreted as specifying the presence of the stated features, integers, steps or components referred to, but not to preclude the presence or addition of one or more other feature, integer, step, component or group thereof. 'ntellectualThuherty office OF N.Z. 2 2 FEB 1999 I - RECEiVrn I WO 97/00612 PCT/US96/10326 182 CLAIMS What is claimed is:

1. A method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound selected 5 from Formula I, N-oxides and agriculturally suitable salts thereof, E^Z A —N R2 I wherein E is selected from: 10 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 15 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 20 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(=0) 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 25 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 30 floating double bond is attached to A; W is O; S; NH; N(CrC6 alkyl); or NO(CrC6 alkyl); WO 97/00612 PCT/VS96/10326 183 X is H; OR1; S(0)mR!; halogen; CrC6 alkyl; C,-C6 haloalkyl; C3-C6 cycloalkyl; cyano; NH2; NHR1; N(CrC6 alkyOR1; NH(C,-C6 alkoxy); or N(CrC6 alkoxy)Rl; R1 is C]-C6 alkyl; C^Cg haloalkyl; Ci-C^ alkenyl; C2-Cg haloalkenyl; C2-C6 5 alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; C2-C4 alkylcarbonyl; or Co-C, alkoxycarbonyl; R2 is H; C]-C6 alkyl; CrC6 haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; Co-Cg alkynyl; C2-Cg haloalkynyl; C3*C6 cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; hydroxy; CpC2 alkoxy; or acetyloxy; 10 R3 and R4 are each independently halogen; cyano; nitro; hydroxy; Cj-Cg alkyl; Cj-Cg haloalkyl; C2-Cg alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; Cj-C6 alkoxy; C^-Cg haloalkoxy; C2-C6 alkenyloxy; C2~Cg alkynyloxy; Cj-Cg alkylthio; Cj-Cg alkylsulfinyl; Cj-Cg alkylsulfonyl; formyl; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; NH2QO); 15 (CrC4 alkyl)NHC(O); (CrC4 alkyl)2NC(0); Si(R25)3; Ge(R25)3; (R25)3Si-OC-; 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 20 alkenylene or C3-C5 haloalkenylene each optionally substituted with 1-2 CrC3 alkyl; R5 is H; Cj-Cg alkyl; Cj-Cg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; 25 Y is -O-; -S(0)n-; -NR*5-; -C(=0)-; -CH(ORl5)-; -CHR*-; -CHR6CHR6-; -CR6=CR6-; -OC-; -CHRl50-; -OCHR15-; -CHR15S(0)n-; -S(0)nCHR15-; -CHR150-N=C(R7)-; -(R7)C=N-OCH(R15)-; -C(R7)=N-0-; -0-N=C(R7)-; -CHR150C(=0)N(R15)-; -CHR15OC(=S)N(R15)-; -CHR150C(=0)0-; -CHR15OC(=S)0-; -CHR150C(=0)S-; -CHR15OC(=S)S-; 30 -CHRl5SC(=0)N(Ri5)-; -CHRlsSC(=S)N(R15)-; -CHR15SC(=0)0-; -CHR15SC(=S)0-; -CHR15SC(=0)S-; -CHR15SC(=S)S-; -CHR 15SC(=NR15)S-; -CHR15N(R15)C(=0)N(R15)-; -CHR150-N(R15)C(=0)N(R15)-; -CHR150-N(R15)C(=S)N(R15)-; -CHR150-N=C(R7)NR15-; -CHR1 SO-N=C(R7)OCH2-; 35 -CHRl50-N=C(R7)-N=N-; -CHR150-N=C(R7)-C(=0)-; -CHR150-N=C(R7)-C(=N-A2-Z1)-A' -; WO 97/00612 l*CT/US96/l0326 184 -CHRl-'0-N=C(R7)-C(R7)=N-A--A3-; -CHR150-N=C(-C(R7)=N-A2-Z! -CHR150-N=C(R7)-CH20-;-CHR150-N=C(R7)-CH2S-: -0-CH2CH20-N=C(R7)-;-CHR150-C(RI5)=C(R7)-;-CHR150-C(R7)=:N-; -CHR15S-C(R7)=N-; -C(R7)=N-NR15-; -CH=N-N=C(R7)-; 5 -CHR15N(R15)-N=C(R7)-; -CHRl5N(COCH3)-N=C(R7)-; -0C(=S)NR15C(=0)-; -CHR6-C(=W1)-A1 -CKRSCHR^C^V/^-A1-; -CR6=CR6-C(=W1)-A1 -C=C-C(=W1)-A1 -; -N=CR6-C(=Wl)-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 10 on the right side of the linkage is bonded to Z; Zl is H or -A3-Z; V/l isOorS; A1 is O; S; NR15; or a direct bond; A2 is 0;NR15; or a direct bond; 15 A3 is -C(=0)-; -S(0)2-; or a direct bond; each R6 is independendy H; 1-2 CH3; C2-C3 alkyl; CrC3 alkoxy; C3-Cg cycloalkyl; formylamino; C2-C4 alkylcarbonylamino; C2-C4 alkexycarbonylamino; NH2C(0)NH; (CrC3 alkyl)NHC(0)NH; (Ci-C3 alkyl)2NC(0)NH; N(C]-C3 alkyl)2; piperidinyl; morpholinyl; 20 1-2 halogen; cyano; or nitro; each R7 is independently H; Cj-Cg alkyl; Cj-C6 haloalkyl; Cj-Cg alkoxy; CpCg haloalkoxy; CpCg alkylthio; C]-C6 alkylsulfinyl; CrCg alkylsulfonyl; CrCg haloalkylthio; Cj-Cg haloalkylsulfinyl; Cj-Cg haloalkylsulfonyl; C2-Cg alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-Cg haloalkynyl; C3-Cg 25 cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy; amino; NH(CrC6 alkyl); N(CrCg alkyl)2; or morpholinyl; each Z is independently selected from: i) Cj-Ci0 alkyl, C2-Cjo alkenyl, and C2-C]Q alkynyl each substituted with R9 and optionally substituted with one or more R10; 30 ii) C3-Cg cycloalkyl, CyCg cycloalkenyl and phenyl each substituted with R-' 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 35 heterocyclic ring systems, each heterocyclic ring system containing 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen, and WO 97/006 J 2 PCT/US96/10326 185 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; 5 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(=0) 10 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; 15 each Q is independently selected from the group -CHR13-, -NR13-, -O-, and -S(0)p-; R8 is H; 1-2 halogen; Cj-Cg alkyl; Cj-Cg haloalkyl; Cj-Cg alkoxy; Cj-Cg haloalkoxy; Cj-Cg alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C5-C6 alkylthio; Cj-Cg haloalkylthio; Cj-Cg alkylsulfinyl; Cj-Cg alkylsulfonyl; 20 C3-C6 cycloalkyl; C3-C6 alkenyloxy; CC>2(Cj-Cg alkyl); NH(Cj-C6 alkyl), N(Cj-C6 alky 1)2; cyano; nitro; SiR19R20R21; or GeR19R20R2); R9 is H; 1-2 halogen; Cj-Cg alkyl; Cj-Cg haloalkyl; Cj-Cg alkoxy; Cj-Cg haloalkoxy; C^-Cg alkenyl; Co-Cg haloalkenyl; C2-Cg alkynyl; Cj-Cg alkylthio; Cj-Cg haloalkylthio; Cj-Cg alkylsulfinyl; Cj-Cg alkylsulfonyl; 25 C3*Cg cycloalkyl; C3-C6 alkenyloxy; CCtyC j-Cg alkyl); NH(C] -C6 alkyl); N(Cj-Cg alkyl)2; -C(R18)=NOR17; cyano; nitro; SFs; 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; 30 each R1C) is independently halogen; Cj-C4 alkyl; Cj-C.} haloalkyl; C1-C4 alkoxy; nitro; or cyano; or when R9 and an R!0 are attached to adjacent atoms on Z, R9 and said adjacently attached R!0 can be taken together as -OCH2O- or -OCH2CH2O-; each CH2 group of said taken together R9 and R10 optionally substituted with 1-2 35 haloeen; or WO 97/(i06l2 PCT/US96/10326 186 when Y and an Ri0 are attached to adjacent atoms on Z and V is ® -CHR150-N=C(R7)-, -0-N=C(R7K -0-CH:CH:0-N=C(R7)-, -CHR150-C(R15)=C(R7)-, -CH=N-N=C(R7)-, -CHR15N(Rt5)-N=C(R7)- or -CHRl3N(COCH3)-N=C(R7)-, R7 and said adjacently attached R10can be 5 taken together as -(CH2)r-J- such that J is attached to Z; J is -CHr; -CH2CH2-; -OCHr; -CH20-; -SCHr; -CH2S-; -N(R,6)CH2-; or -CH2N(R16)-; each CH2 group of said J optionally substituted with 1 to 2 CH3; Rl1 and R12 are each independently 1-2 halogen; C1-C4 alkyl; C1-C4 haloalkyl; 10 C2-Cg alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C2-C6 alkoxyalkyl; C2-Cg alkylthioalkyl; C3-C6 alkoxyalkynyl; C7-C10 tetrahydropyranyloxyalkynyl; benzvloxymethyl; CrC4 alkoxy; Cj-C4 haloalkoxy; C3-Cg alkenyloxy; C3-Cg haloalkenyloxy; C3-C6 alkynyloxy; C3-C6 haloalkynyloxy; Cj-C^ alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; 15 C2-C6 alkylthioalkoxy; Cj-C4 alkylthio; C]-C4 haloalkylthio; C1-C4 alkylsulfinyl; C1-C4 haloalkylsulfinyl; C^-C^ alkylsulfonyl; CrC4 haloalkylsulfonyl; C3-Cg alkenylthio; C3-Cg haloalkenylthio; C2-C() alkylthioalkylthio; nitro; cyano; thiocyanato; hydroxy; N(R26)2; SF5; Si(R25)3; Ge(R25)3; (R25)3Si-OC-; OSi(R25)3; OGe(R25)3; C(=0)R26; 20 C(=S)R26; C(=0)0R26; C(=S)OR26; C(=Q)SR26; C(=S)SR26; C(=0)N(R26)2; C(=S)N(R26)2; 0C(=0)R2&; OC(=S)R26; SC(=0)R26; SC(=S)R26; N(R26)C(=0)R26; N(R26)C(=S)R26; 0C(=0)0R27; 0C(=0)SR27; 0C(=0)N(R26)2; SC(=0)0R27; SC(=0)SR27; S(0)2OR26; S(0)2N(R26)2; 0S(0)2R27; N(R26)S(0)2R27; or phenyl, phenoxy, benzyl, 25 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; CpC6 alkyl; CpQj haloalkyl; or phenyl optionally substituted with halogen, C1-C4 alkyl, Cj-C4 haloalkyl, C]-C4 alkoxy, Cj-Cj 30 haloalkoxy, nitro or cyano; R14 is H; halogen; CrCg aikyl; CpCg haloalkyl; C2-C6 alkenyl; C2-Q haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; or C3-Cg cycloalkyl; each R15 is independently H; Cj-C3 alkyl; C3-Cg cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C1-C4 alkyl. 35 C,-C4 haloalkyl, C|-C4 alkoxy, C]-C4 haloalkoxy, nitro or cyano; or WO'>7/00612 F'CT/TJS96/I0326 187 when Y is -CHRl5N(R15)C(=0)N(R15)-, the two R15 attached to nitrogen atoms on said group can be taken together as -(CH2V; or when Y is -CHR150-N=C(R7)NR15-, R7 and the adjacently attached R1? can be taken together as -CH2-(CH2)S-; -0-(CH2>s-; -S-(CH2)s-; or 5 -N(C)-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-Cg cycloalkyl; or 10 phenyl optionally substituted with halogen, C j-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, Cj-C4 haloalkoxy, nitro or cyano; R19, R20, R21, R22, R23, and R2^ are each independently Cj-Cg alkyl; C2*Cg alkenyl; C]-C4 alkoxy; or phenyl; each R25 is independently CrC4 alkyl; CrC4 haloalkyl; C2-C4 alkenyl; CrC4 15 alkoxy; or phenyl; each R26 is independently H; Cj-Cg alkyl; Cj-Cg haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-Cg cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C]-C4 alkyl, Cj-C4 haloalkyl, Ci~C4 alkoxy, Cj-04 haloalkoxy, nitro or cyano; 20 each R27 is independently CrC6 alkyl; Cj-Cg haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, Cj-C4 alkyl, Cj-C4 haloalkyl, C]-C4 alkoxy, CJ-C4 haloalkoxy, nitro or cyano; m, n and p are each independently 0, 1 or 2; 25 r is 0 or 1; and s is 2 or 3; provided that (i) when E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; X is OR1. S(0)mR! or halogen; Y is -0-, -SfO)n-. -NR15-, 30 -C(=0)-,-CH(0R15)-, -CHR6-, -CHR6CHR6-. -CR6=CR6-, -C=C-, -CHR150~, -OCHR15-, -CHRt5S(0)n-, -S(0)nCHR15-, -CHR150-N=C(R7)-, -(R7)C=N-OCH(R15)-, -C(R7)=N-0-, -0-N=C(R7)-, -CHR150C(=0)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 35 heterocyclic ring system each substituted with R9 and optionally substituted with one or more R10; 188 "■ 31 0 8^ (ii) wht?n E is a naphthalene ring optionally substituted with one of R3, RJ. or both R3 and R4; R3 or R4 is Si(R-5)3 or Ge(R-5)3; and Y is -0-, -S(0)n-, -C(=0)-, -CHR6-. -CHR6CHR6-, -CR6=CR6-, C=C-, -OCHR'5-, -S(0)nCHR15- or a direct bond; then Z is other than C j-Cj0 alkyl, C2-C10 alkenyl or C2-C10 alkynyl each substituted with R9 and optionally substituted with one or mors Rt0; (iii) when E is a naphthalene ring optionally substituted with one of R3, R4, or both R3 and R4; R3 or R4 is Si(R-5)3 or Ge(R25)3; and Y is -S(0)n-, -C(~0)-r -C=C- or a direct bond; then Z is other than phenyl substituted with R9 and optionally substituted with one or more R10; and (iv) when E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; W is 0; G is C; A is NR5 with the floating double bond attached to G; X is OR1, and R1 is C2-Cg alkenyl, C2-Cg haloalkenyl, C2-Cg alkynyl, C2-C6 haloalkynyl, C2-C4 alkylcarbonyl or C2-C4 alkoxy carbonyl; then Y-Z is other than Cj-Cjo alkyl or CpCjQ alkoxy.

2. A compound selected from Formula IA, N-oxides arid agriculturally suitable salts thereof, e-Y-Z I •°yw A —N R2 IA wherein E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; A is 0 or N; G is C or N; provided that when G is C, then A is O 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; WisO; X is OR'; R1 is C1-C3 alkyl; R2 is H or CpCj alkyl; R3 and R4 are each independently halogen; cyano; nitro; Cj-Cg alkyl; Cj-Cg haloalkyl; CpCg alkoxy; or Cj-Cg haloalkoxy; CpCg alkylsulfonyl; C2-Cg alkylcarbonyl; C2-Cg alkoxycarbonyl; (C[-C4 alkyl)NHC(O); (CrC4 alkyl)2NC(0); benzoyl; or phenylsulfonyl; 310 8« V is -0-; -S(0)n-: -NR15-; -C<=0)-; -CH(OR15)-; -CH2-; -CH:CH:-; -CH=CH-; -ChC-; -CH20-; -OCHn-; -CH2S(0)n-; -S(0)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; CpCg alkyl; C|-C6 haloalkyl; CrCg alkoxy; CrC6 haloalkoxy; C2-C6 alkenyi; C2-Cg haloalkenyl; C2-C6 alkynyl; CrC6 alkylthio; CrC6 haloalkylthio; CpCg alkylsulfinyl; C|-C6 alkylsulfonyl; C3-C6 cycloalkyl; C3-C6 alkenyloxy; C02(Ci-C6 alkyl); NH(CrC6 alkyl); N(CrCg 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 PJR12, or both R11 and R12; provided that when Z is pyrazinyl, then R9 is other than H or Cj-Cg haloalkyl; each R10 is independently halogen; CpC4 alkyl; CpC4 haloalkyl; C]-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 -OCH20- 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; C]-C4 alkyl; Cj-C4 haloalkyl; C2-Cg alkenyl; C2-C6 haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C2-Cg alkoxyalkyl; C2-Cg alkylthioalkyl; C3-C6 alkoxyalkynyl; C7-C10 tetrahydropyranyloxyalkynyl; benzyloxymethyl; CrC4 alkoxy; C]-C4 haloalkoxy; C3-Cg alkenyloxy; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy; C3-Cg haloalkynyloxy; C2-Cg alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-Cg alkylthioalkoxy; C|-C4 alkylthio; CpC4 haloalkylthio; C1-C4 alkylsulfinyl; C1-C4 haloalkylsulfinyl; C1-C4 alkylsulfonyl; Ci*C4 haloalkylsulfonyl: C3-Cg alkenylthio; C3-C6 haloalkenylthio; C2-Cg alkylthioalkyIthio; nitro; cyano; thiocyanato; hydroxy; N(R26)2; SFs; Si(R25)3; Ge(R25)3; (R25)3Si-C=C-; OSi(R25)3; OGe(R25)3; C(=0)R26; C(=S)R26; C(=0)0R26; C(=S)OR26; C(=0)SR26; C(=S)SR2<5; C(=0)N(R26)2; C(=S)N(R26)2; 0C(=0)R26; OC(=S)R26; SC(=0)R26; SC(=S)R26; N(R26)C(=0)R26; N(R26)C(=S)R26; 0C(=0)0R27; 0C(=0)SR27; 0C(=0)N(R26)2; SC(=0)0R27; SC(=0)SR27; S(0)20R26; S(0)2N(R26)2; 0S(0)2R27; N(R26)S(0)2R27; or phenyl, 190 31 0 (j • phenoxy. benzyl, benzyloxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted with halogen, CrC4 alkyl, C1-C4 haloalkyl, C|-C4 alkoxy, C|-C4 haloalkoxy, nitro or cyano; R> ^ is H; C1-C3 alkyl; or cyclopropyl; R17 and R'8 are each independently H; C1-C3 alkyl; C3-Cg cycloalkyl; or phenyl optionally substituted with halogen, C [-C4 alkyl, C |-C4 haloalkyl, C ]-C4 alkoxy, Q-C4 haloalkoxy, nitro or cyano; r22, r24 aje each independently CrCg alkyl; Cn-Cg alkenyl; C1-C4 alkoxy; or phenyl; each R25 is independently C1-C4 alkyl; CpC4 haloalkyl; C2~C4 alkenyl; CpC4 alkoxy; or-phenyl; each R26 is independently H; CpCg alkyl; CrCg haloalkyl; C2-Cg alkenyl; C2-C haloalkenyl; C2-Cg alkynyl; C2*Cg haloalkynyl; Cj-Cg cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, Q-C4 alkyl, C1-C4 haloalkyl, C!-C4 alkoxy, C]-C4 haloalkoxy, nitro or cyano; each R27 is independently CpCg alkyl; Cj-Cg haloalkyl; C2~Cg alkenyl; C2~Cg haloalkenyl; C2-Cg alkynyl; C2~Cg haloalkynyl; C3-Cg cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C1-C4 alkyl, C1-C4 haloalkyl, Ci*C4 alkoxy, Cj-C4 haloalkoxy, nitro or cyano; and n is 0, 1 or 2; provided that (a) when E is 1,2-phenylene optionaly substituted with one of R-\ R4, or both R3 and R4; R3 is H; R4 is H; R2 is CH3; W is O; G is C; A is O with the floating double bond is attached to G; X is OCH3; Y is O, CH20 or CH2ON=C(CH3); then Z is other than 6-CF3-2-pyrazinyl; and (b) when E is 1,2-phenvlene optionally substituted with one of R3, R4, or both R3 and R4; R3 is H; R4 is H; R2 is CH3; W is O; G is N; A is N with the floating double bond is attached to A; X is OCH3, Y is CH2ON=C(CH3) or CH2S; then Z is other than 6-CF3-2-pyrazinyl.

3. A compound of Claim 2 wherein: R1 is methyl; R2 is methyl; Y is -0-; -S(0)n-; -NR15-; -C(=0)-; -CH(OR15)-; -CH2-; or a direct bond; and 310 8B R9 is H; halogen; CpCg alkyl; C|-Cg haloalkyl; Cj-C6 alkoxy; CpC6 haloalkoxy; CpCg alkylthio; CpCg haloalkylthio; CrC6 alkylsulfinyl; C|-Cg alkylsulfonyl; C3-C6 cycloalkyl; CCbCCj-Cg alkyl); -C(R18)=NOR17; cyano; nitro; SF5; SiR--R-3R24; or GeR22R23R24; or R9 is phenyl, benzyl, phenoxy, pyridinyl, thienyl, furanyl, or pyrimidinyl each optionally substituted with one of R1', R1-, or both R11 and R12.

4. A compound of Claim 3 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 -0-; and R9 is phenyl optionally substituted with one of R1R12, or both R11 and R12. WO 97/00612 ^ PCT/US96/10326 3l0 8bL> I9l

5. The compound of Claim 3 which is selected from the group: 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-l,2,4-thiadiazol-5-yl]oxy]phenyl]-2.4-dihydro-5-methoxy-2-methyl-3//-1,2,4-triazol-3-one; 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-l ,2,4-thiadiazol-5-yl]oxy]-6-5 methylphenyl]-2,4-dihydro-5-methoxy-2-methyl-3tf-l,2,4-triazol-3-one; 4-[2-[[3-( 1,1 -dimethylethyl)-1,2,4-thiadiazol-5-yl]oxy]-6-methylphenyl]-2,4-dihydro-5-methoxy-2-methyl-3//-1,2,4-iriazol-3-one; 4-[2-[[3-( 1,1-dimethylethyl)-1,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4-dihvdro-5-methoxy-2-methyl-3//-1,2,4-triazol-3-one; 10 4-[2-[[3-(3,4-dichlorophenyl)-l,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4-dihydro-5- methoxy-2-methyl-3//-l,2,4-triazol-3-one; 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[3-[3-(trifluoromethoxy)phenyl]-l,2,4-thiadiazol-5-yl]oxy]phenyl]-3//-l,2,4-triazol-3-one; 4-[2-[[3-(4-bromophenyl)-l,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4-dihydro-5-15 methoxy-2-methyl-3/f-1,2,4-triazol-3-one; 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[5-methyl-4-[3-(trifluoromethyl)phenyl]-2-thiazolyl]oxy]phenyl]-3//-1,2,4-triazol-3-one; and 2,4-dlhydro-5-methoxy-2-Tnethyl-4-[2-[[6-[4-(trifluoromethyl)phenyl]-2-pyrazinyl]oxy]phenyl]-3H-l,2,4-triazol-3-one. 20

6. A compound selected from Formula IB, N-oxides and agriculturally suitable salts thereof, x^fYw A—N R2 IB wherein 25 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 30 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 WO 97/00612 PCT/US96/10326 192 bicyclic aromalic heterocyclic ring systems, each heterocyclic ring system containing 1 to 6 heteroatoms independently selected from the gro".p nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more 5 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(=0) 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 10 ring members, each aromatic heterocyclic ring system optionally substituted with one of R3, R4, or both R3 and R4; AisO; 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 15 floating double bond is attached to A; W is O; S; NH; N(CrC6 alkyl); or NO(CrC6 alkyl); X is H; OR1; S(0)mR'; halogen; CpCg alkyl; CpCg haloalkyl; C3-Cg cycloalkyl; cyano; NH2; NHR1; N(CrC6 alkyDR1; NH(C,-C6 alkoxy); or N(CrC6 alkoxy)R1; 20 R1 is Cj-Cgj alkyl; Cj-Cg haloalkyl; C2-Cg alkenyl; C2-C6 haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; R2 is H; Cj-Cg alkyl; Cj-Cg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 25 alkoxycarbonyl; hydroxy; Cj -C2 alkoxy; or acetyloxy; R3 and R4 are each independently halogen; cyano; nitro; hydroxy; CrCg alkyl; Cj-Cg haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; Cj-Cg alkoxy; CpCg haloalkoxy; C2-Cg alkenyloxy; C2-Cg alkynyloxy; Cj-Cg alkylthio; Cj-Cg alkylsulfinyl; CpCg alkylsulfonyl; formyl; 30 CrC6 alkylcarbonyl; C2-C6 alkoxycarbonyl; NH2C(0); (CrC4 alkyl)NHC(O); (CrC4 alkyl)2NC(0); Si(R25)3; Ge(R25)3; (R-5)3Si-C=C-; or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R8 and optionally substituted with one or more R'°; or when E is 1,2-phenylene and R3 and R4 are attached to adjacent atoms. R3 and R4 35 can be taken together as C3-C5 alkyJene, C3-C5 haloalkylene, C3-C5 WO 97/00612 PCT/US96/10326 193 alkenylene or C3-C5 haloalkenylene each optionally substituted with 1-2 CrC3 alkyl; R5 is H; CpCf, alkyl; C|-C6 haloalkyl; C2-Ch alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 5 alkoxycarbonyl; Y is -Os -S(0)n-; -NR15-; -C(=0)-; -CH(OR15)-; -CHR6-; -CHR6CHR6-; -CR6=CR6-; -C=C-; -CHR150-; -OCHR15-; -CHR15S(0)n-; -S(0)nCHR15-; -CHR150-N=C(R7)-; -(R7)C=N-0CH(R15)-; -C(R7)=N-0-; -0-N=C(R7)-; -CHR150C(=0)N(R!5)-; -CHR15OC(=S)N(R15)-; -CHR150C(=0)0-; 10 -CHR 150C(=S)0-; -CHR150C(=0)S-; -CHR15OC(=S)S-; -CHR15SC(=0)N(R15)-; -CHR15SC(=S)N(R'5)-; -CHR15SC(=0)0-; -CHR15SC(=S)0-; -CHR15SC(-0)S-; -CHR15SC(=S)S-; -CHR15SC(=NR15)S-; -CHR15N(R15)C(=0)N(R15)-; -CHR150-N(R15)C(=0)N(R15)-; -CHR150-N(R15)C(=S)N(R15)-; 15 -CHR150-N=C(R7)NR15-; -CHR150-N=C(R7)0CHr; -CHR150-N=C(R7)-N=N-;-CHR150-N=C(R7)-C(=0)-; -CHR150-N=C(R7)-C(=N-A2-Z1)-A1-; -CHR150-N=C(R7)-C(R7)=N-A2-A3-; -CHR150-N=C(-C(R7)=N-A2-Z1)-; -CHR150-N=C(R7)-CH20-;-CHR150-N=C(R7)-CH2S-; 20 -0-CH2CH20-N=C(R7)-; -CHR150-C(R15)-=C(R7)-; -CHR150-C(R7)=N-; -CHR 15S-C(R7)=N-; -C(R7)=N-NR15-; -CH=N-N=C(R7)-; -CHR15N(R15)-N=C(R7)-; -CHR15N(C0CH3)-N=C(R7)-; -0C(=S)NR15C(=0)-; -CHR6-C(=W1)-A1-; -CHRSCHRS-C^W^-A1-; -CR6=CR6-C(=W1 )-A1 -; -CsC-C^W^-A1-; -^CR^-C^W^-A1-; or a 25 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 isHor-A3-Z; W1 isOorS; 30 A1 is O; S; NR15; or a direct bond; A2 is O; NR15; or a direct bond; A3 is -C(=0)-; -S(0)2-; or a dircct bond; each R6 is independently H; 1-2 CH3; C2-C3 alkyl; C]-C3 alkoxy; C3*C6 cycloalkyl; forrnylamino; C2-C4 alkylcarbonvlamino; C2-C4 35 alkoxycarbonylamino; NH2C(0)NH; (C1-C3 alkyl)NHC(0)NH; WO 97/00612 PCT/US96/J0326 194 (C]-C3 alkylhNC(0)NH; N(Ci-C3 alkylb; pipcridinyl; morpholinyl; 1 -2 halogen; cyano; or nitro; each R7 is independently H; C|-C(l alkyl; Cj-C6 haloalkyl; C|-C^ alkoxy; C]-C(l haloalkoxy; Cj-Cg alkylthio; Cj-Cg alkylsulfinyl; CpCg alkylsulfonyl; CpCf, 5 haloalkylthio; Cj-Cg haloalkylsulfinyl; Cj-C6 haloalkylsulfonyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy; amino; NHCCpQ, alkyl); N(CI-Cfl alky 1)2', or morpholinyl; each Z is independently selected from: 10 i) CpCjo alkyl, C2-C10 alkenyl, or C2-C10 alkynyl each substituted with R9 and optionally substituted with one or more R10; ii) C3~Cg cycloalkyl, C3-Cg 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 15 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 20 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 25 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(=0) and S(0)2, and any remaining rings as aromatic carbocyclic rings, each multicyclic ring system substituted with R9 and optionally substituted with 30 one or more R1 °; and v) adamantyl substituted with R9 and optionally substituted with one or more Rlf); each Q is independently selected from the group -CHR13-, -NR13-, -0-, and -S(0)p-; 35 R8 is H; 1-2 halogen; Cj-Cg alkyl; Cj-Cg haloalkyl; Cj-Cg alkoxy; CrC6 haloalkoxy; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; Cj-Cf, # WO 97/00612 PCT/US96/10326 195 alkylthio; CpCg haloalkylthio; CpCg alkylsulfinyl; CpCg alkylsulfonyl; cycloalkyl; C3-Cg alkenyloxy; C02(C]-Ch alkyl); NH(C )-Cg alkyl); N(C|-Cg alkyl)2; cyano; nitro; SiR19R20R21; or GeRl9R20R21; R9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl. thienyloxy, 5 furanyl, pyrimidinyl, or pyrimidinyloxy each substituted with R11 and optionally substituted with R12; each R10 is independently halogen; CpC.^ alkyl; CpC4 haloalkyl; CpC4 alkoxy; nitro; or cyano; or when R9 and an R10 are attached to adjacent atoms on Z, R9 and said adjacently 10 attached R10 can be taken together as -OCH2O- or -0CH2CH20-; each CH2 group of said taken together R9 and R10 optionally substituted with 1-2 halogen; or when Y and an R1® are attached to adjacent atoms on Z and Y is -CHR150-N=C(R7)-, -0-N=C(R7)-, -O-CH2CH2O-N=CCR7)-, 15 -CHR150-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 -CHr; -CH2CH2-; -OCH2-; -CH20-; -SCH2-; -CH2S-; -N(R16)CH2-; or -CH2N(R16)-; each CH2 group of said J optionally substituted with 1 to 2 20 CH3; R11 is C2-Cg alkenyl; C2-C6 haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl: C2-C6 alkoxyalkyl; C2-Cg alkylthioalkyl; C3-Cg alkoxyalkynyl; C7-CK) tetrahydropyranyloxvalkynyl; benzyloxymethyl; C3-C6 alkenyloxy; C3-C6 haloalkenyloxy; C3-Cg alkynyloxy; C3-Cg haloalkynyloxy; C2-Cg 25 alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-Cg alkylthioalkoxy; C] -C4 alkylthio; C1-C4 haloa'.kylthio; C1-C4 alkylsulfinyl; CpC4 haloalkylsulfinyl; CpC4 alkylsulfonyl; C1-C4 haloalkylsulfonyl; C3*Cg alkenylthio; C3*Cg haloalkenylthio; C2-Cg alkylthioalkylthio; thiocyanato; hydroxy; N(R26)2'. SF5; (R25)3Si-C=C-; OSi(R25)3; OGe(R25)3; C(=0)R26; C(=S)R26; 30 C(=0)0R26; C(=S)OR26; C(=0)SR26; C(=S)SR26; C(=0)N(R26)2; C(=S)N(R26):; 0C(=0)R26; OC(=S)R26; SC(=0)R26; SC(=S)R26; N(R26)C(=0)R26; N(R26)C(=S)R26; 0C(=0)0R27; 0C(=0)SR27; 0C(=0)N(R26)2; SC(=0)0R27; SC(=0)SR27; S(0)20R26; S(0)2N(R26)2; 0S(0)2R27; N(R26)S(0)2R27; or phenyl, phenoxy, benzyl, benzyloxy, 35 phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted WO 97/00612 PCT/US96/10326 196 with halogen, C|-C4 alkyl, C]-C4 haloalkyl, C]-C4 alkoxy, C|-C4 haloalkoxy, nitro or cyano; R12is 1-2 halogen; CpC4 alkyl; CrC4 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-Cg alkynyl; Cn-C^ haloalkynyl; C2-Cg alkoxyalkyl; C2-Cg 5 alkylthioalkyl; C3-C6 alkoxyalkynyl; C7-C;0 tetrahydropyranyloxyalkynyl; benzyloxymethyl; C]-C4 alkoxy; C]-C4 haloalkoxy; C3-C6 alkenyloxy; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy; CyC(, haloalkynyloxy; C2-Cg alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; CrC4 alkylthio; CrC4 haloalkylthio; C]-C4 alkylsulfinyl; CrC4 haloalkylsulfinyl; 10 Ci-C4 alkylsulfonyl; C1-C4 haloalkylsulfonyl; C3-C6 alkenylthio; C3-Cg haloalkenylthio; C2-Cg alkylthioalkylthio; nitro; cyano; thiocyanato; hydroxy; N(R26)2; SF5; Si(R25)3; Ge(R25)3; (R-5)3Si-C=C-; OSi(R25)3; OGe(R25)3; C(=0)R26; C(=S)R26; C(=0)0R-6; C(=S)OR26; C(=0)SR26; C(=S)SR26; C(=0)N(R26)2; C(=S)N(R26)2; 0C(=O)R26; OC(=S)R26; SC(=0)R26; 15 SC(=S)R26; N(R26)C(=0)R26; N(R26)C(=S)R26; 0C(=0)0R27; OC(=0)SR27; 0C(=0)N(R26)2; SC(=0)0R27; SC(=0)SR27; S(O)20R26; S(0)2N(R26)2; 0S(0)2R27; N(R26)S(0)2R27; or phenyl, phenoxy, benzyl, benzyloxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each optionally substituted with halogen, Cj-C4 alkyl, Cj-C4 haloalkyl, CrC4 alkoxy, Cj-C4 20 haloalkoxy, nitro or cyano; each R13 is independently H; Cj-C6 alkyl; Cj-Cg haloalkyl; or phenvl optionally substituted with halogen, Cj-C4 alkyl, Cj-C4 haloalkyl, Cj-C4 alkoxy, Cj-C4 haloalkoxy, nitro or cyano; R14 is H; halogen; CpCg alkyl; Cj-Cg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; 25 C2-Cg alkynyl; C2-Cg haloalkynyl; or C3-Cg cycloalkyl; each R1^ is independently H; CJ-C3 alkyl; C3-Cg cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, Cj-C4 alkyl, C]-C4 haloalkyl, CpC4 alkoxy, CpC4 haloalkoxy, nitro or cyano; or when Y is -CHR15N(R15)C(=Q)N(R15)-, the two R15 attached to nitrogen atoms 30 on said group can be taken together as -(CH2)S-; or when Y is -CHR150-N=C(R7)NR15-, R7 and the adjacently attached R1 5 can be taken together as -CH2-(CH2)S-; -0-(CH2)s-; -S-(CH2)s-; or -N(CpC3 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 35 carbon and the moiety on the right side of the linkage is bonded to the nitrogen; WO 97/00612 PCT/US96/10326 197 R16 is H; C1-C3 alkyl; C3-Cg cycloalkyl; or phenyl optionally substituted with halogen, C|-C4 alkyl, C]-C4 haloalkyl, Cj-C4 alkoxy, C)-C4 haloalkoxy, nitro or cyano; R19, R20, and R21 are each independently CpCg alkyl; Co-Cg alkenyl; C]-C4 5 alkoxy; or phenyl; each R25 is independently C]-C4 alkyl; CpC4 haloalkyl; Cn-Q alkenyl; C1-C4 alkoxy; or phenyl; each R26 is independently H; CpCg alkyl; C]-C6 haloalkyl; Co-Cg alkenyl; Ci-Cg haloalkenyl; CVCg alkynyl; C2-Cg haloalkynyl; C3-C6 cycloalkyl; or phenyl 10 or benzyl, each optionally substituted on the phenyl ring with halogen, CpC4 alkyl, Cj-C4 haloalkyl, CpC4 alkoxy, CpC4 haloalkoxy, nitro or cyano; each R27 is independendy CpCg alkyl; CpCg haloalkyl; C2~Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C]-C4 15 alkyl, CpC4 haloalkyl, C]-C4 alkoxy, CpC4 haloalkoxy, nitro or cyano; m, n and p are each independently 0, 1 or 2; r is 0 or 1; and s is 2 or 3.

7. A compound of Claim 6 wherein: 20 E is selected from the group 1,2-phenvlene; 1,5-, 1,6-, 1,7-, 1,8-, 2,6-, 2,7-, 1,2-, and 2,3-naphthalenediyl; l//-pyrrole-l,2-, 2,3- and 3,4-diyl; 2,3- and 3.4-furandiyl; 2,3- and 3,4-thiophenediyl; l//-pyrazole-l,5-, 3,4- and 4.5-diyl; 1//-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; 25 l//-l,2,3-triazole-l,5- and 4,5-diyl; 2//-l,2,3-triazole-4,5-diyl; 1//- 1,2,4-triazole-1,5-diyl; AH-1,2,4-triazole-3,4-diyl; l,2,3-oxadiazole-4,5-diyl; l,2.5-oxadiazole-3,4-diyl; 1.2,3-thiadiazole-4,5-diyl; 1,2,5-thiadiazole-3,4-diyl; 1 //-tetrazole-1,5-diyl; 2,3- and 3,4-pyridinediyl; 3,4- and 4,5-pyridazinediyl; 4,5-pyrimidinediyl; 30 2,3-pyrazinediyl; l,2,3-triazine-4,5-diyl; l,2,4-triazine-5.6-diyl; 1//-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[£»]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; l//-indazole-l ,4-, 35 1.5-, 1,6-, 1,7-, 3,4-, 3.5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; l//-benzimidazole-l,4-, 1,5-, 1,6-, 1,7-, 2,4-, 2,5-, 2.6-, 2.7-, 4.5-, 5,6- and WO 97/00612 PCT/US96/10326 198 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-, 2,1-, 4,5-, 5,6- and 6,7-benzoxazolediyl; l,2-benzisothinzole-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-, 5 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 10 7,8-quinazolinediyl; 2,5-, 2,6-, 2,7-, 2,8-, 2,3-, 5,6-, 6,7- and 7,8-quinoxalinediyl; l,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,l-b]thiazole-2,6-, 2,7-, 3,6-, 3,7-, 2,3- and 6,7-diyl; thiazolo[2,3-c]-l,2,4-triazoIe-2,5-, 2,6-, 5,6-diyl; 15 2-oxo-l,3-benzodioxole-4,5- and 5,6-diyl; l,3-dioxo-l/f-isoindole-2,4-, 2,5- 4,5- and 5,6-diyl; 2-oxo-2H-l-benzopyraR-3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 5,6-, 6,7- and 7,8-diyl; [l,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-2//-l,3-benzoxazine-3,5-, 3,6-, 3,7-, 3,8-, 5,6-, 6,7-20 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-c/]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-l,l,3-trioxo-l,2-benzisothiazole-2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6-25 and 6,7-diyl; l,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-4//-cyclohepta[&]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 30 substituted with one of R3, R4, or both R3 and R4; Wis O; R1 isCpC3 alkyl orCpC3 haloalkyl; R2 is H; CpCg alkyl; CpCg haloalkyl; or C3-Cg cycloalkyl; R3 and R4 are each independently halogen; cyano; nitro; CpCg alkyl; CpCg 35 haloalkyl; CpCg alkoxy; CpCg haloalkoxy; CpCg alkylthio; CpCg PCT/US96/10326 199 alkylsulfonyl; C2-Cg alkylcarbonyl; CVQ, alkoxycarbonyl; (CpC4 alkyl)NHC(O); (C1-C4 alkyl)2NC(Oj; benzoyl; or phenylsulfonyl; is -O-; -S(0)n-; -NR15-; -C(=0)-; -CH(OR'5)-; -CH:-; -CH:CH2-; -CH=CH-; -CsC-; -CH20-; -OCHr; -CH2S(0)n-; -S(0)nCH2-; -CH20-N=C(R7)-; -(R7)C=N-OCH(R15)-; -C(R7)=N-0-; or a direct bond; 7 is H; CpCg alkyl; CpCg haloalkyl; CpCg alkoxy; CpCg alkylthio; C2-Cg alkenyl; C2-Cg alkynyl; Cs-Cg cycloalkyl; halogen; or cyano; or hen Y and an R1^ are attached to adjacent atoms on Z and Y is -CH20-N=C(R7)-, R7 and said adjacently attached R10 can be taken together as -(CH2)r-J- such that J is attached to Z; is selected from the group Ci-C10 alkyl; C3-C8 cycloalkyl; phenyl; naphthalenyl; anthracenyl; phenanthrenyl; 1/f-pyrrolyl; furanyl; thienyl; lH-pyrazolyl; l//-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl; thiazolyl; 1//-1,2,3-triazolyl;2/f-l,2,3-triazolyl; l//-l,2,4-triazolyl;4/M,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; l//-tetrazolyl; 2//-tetrazolyl; pyridinyl; pyridazinyl; pyrimidinyl; pyrazinyl; 1,3,5-triazinyl; 1,2,4-triazinyl; 1,2,4,5-tetrazinyl; 1/f-indolyl; benzofuranyl; benzo[fr]thiophenyl; ltf-indazolyl; l//-benzimidazolyl; benzoxazolyl; benzothiazolyl; quinolinyl; isoquinolinyl; cinnolinyl; phthalazinyl; quinazolinyl; quinoxalinyl; 1,8-naphthyridinyl; pteridinyl; 2,3-dihydro- ltf-indenyl; 1,2,3,4-tetrahydronaphthalenyl; 6,7,8,9-tetrahydro-5/f-benzocycloheptenyl; 5,6,7,8,9,10-hexahydrobenzocyclooctenyl; 2,3-dihydro-3-oxobenzofuranyl; 1.3-dihydro-1 -oxoisobenzofurany 1; 2,3-dihydro-2-oxobenzofuranyl; 3.4-dihydro-4-oxo-2//-1-benzopyranyl; 3,4-dihydro-1 -oxo-1 //-2-benzopy rany 1; 3,4-dihydro-3-oxo-1 /f-2-benzopyranyl; 3,4-dihydro-2-oxo-2//-1-benzopyranyl; 4-o\o-4H- 1-benzopyranyl; 2-OXO-2H-1 -benzopyranyi; 2,3,4,5-tetrahydro-5-oxo-1 -benzoxepinyl; 2,3,4,5-tetrahydro-2-oxo-1 -benzoxepinyl; 2.3-dihydro-1,3-dioxo-1 //-isoindolyl; 1,2,3,4-tetrahydro-1,3-dioxoisoquinolinyl; 3.4-dihydro-2,4-dioxo-2tf-1,3-benzoxazinyl; 2-oxo-1,3-benzodioxyl; 2,3-dihydro-1,1,3-trioxo-l,2-benzisothiazolyl; 9//-fluorenyl; azulenyl; and WO 97/00612 PCT/US96/10326 200 thiazolo[2,3-cj-l,2,4-triazolyl; each group substituted with R9 and optionally substituted with one or more R10; and R15 is H; CpC3 alkyl; or C3*Cg cycloalkyl.

8. A compound of Claim 7 wherein: 5 E is selected from the group 1,2-phenvlene; 1.6-, 1,7-, 1,2-, and 2,3-naphthaienediyl; 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[6]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, 10 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; 15 R7 is H; Cj-Cg alkyl; CpCg haloalkyl; CpCg alkoxy; CpCg alkylthio; C2-Cg alkenyl; C2-Cg alkynyl; cyclopropyl; halogen; or cyano; or when Y and an R10 are attached to adjacent atoms on Z and Y is -CH20-N=C(R1')-, R7 and said adjacently attached R10 can be taken together as -(CH2)r-J- such that J is attached to Z; 20 J is -CH2- or -CH2CH2-; and r is 1.

9. The compound of Claim 8 which is selected from the group: 4-[2-[[3-(3-ef.hynylphenyl)-l,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4-dihydro-5-methoxy-2-methyl-3W-1,2,4-triazol-3-one; and 25 [3-[5-[2-( 1,5-dihydro-3-methoxy- l-methyl-5-oxo-4//-1,2,4-triazol-4- yl)phenoxy]-l,2,4-thiadiazol-3-yl]phenyl] trifluoromethanesulfonate.

10. A fungicidal composition comprising a fungicidally effective amount of a compound of any of Claims 2-9 and at least one of a surfactant, a solid diluent or a liquid diluent. 30

11. An arthropodicidal composition comprising an arthropodicidally effective amount of a compound of any of Claims 2-9 and at least one of a surfactant, a solid diluent or a liquid diluent.

12. 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 35 fungicidally effective amount of a compound of any of Claims 2-9. WO 97/(10612 PCT/US96/10326 201

13. A compound selected from Formula 11, .OH A —N \ R2 n wherein 5 E is 1,2-phenylene optionally substituted with one of R3, R4, or both R3 and R4; AisO;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; 10 W is O; S; NH; N(C,-C6 alkyl); or NOfCpCg alkyl); X is OR1; SPhjR1; or halogen; R1 is CpCg alkyl; CpCg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-C6 alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl: C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; 15 R2 is H; CpCg alkyl; CpCg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-C6 haloalkynyl; C3-C5 cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; hydroxy; CpC2 alkoxy; or acetyloxy; R3 and R4 are each independently halogen; cyano; nitro; hydroxy; CpCg alkyl; CpCg haloalkyl; C2-Cg alkenyl; C2-Cg haloalkenyl; C2-Cg alkynyl; C2-Cg 20 haloalkynyl; CpCg alkoxy; CpCg haloalkoxy; C2-Cg alkenyloxy; C2-Cg alkynyloxy; CpCg alkyithio; CpCg alkylsulfinyl; CpCg alkylsulfonyl; formyl; C2-Cg alkylcarbonyl; C2-Cg alkoxycarbonyl; NH2C(0); (CrC4 alkyl)NHC(O); (CrC4 alkyl)2NC(0); Si(R25)3; Ge(R2^3, (R25)3Si-C=C-; or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each 25 substituted with R8 and optionally substituted with one or more R10; or 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 CpC3 alkyl; R5 is H; CpCg alkyl; CpCg haloalkyl; C2-C6 alkenyl; C2-Cg haloalkenyl; C2-C6 30 alkynyl; C2-Cg haloalkynyl; C3-Cg cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; - 202 - R8 is H; 1-2 halogen; C,-C6 alkyl; C,-C6 haloalkyl; CpCg alkoxy; C,-C6 haloalkoxy; C2-C5 alkenyl; C2*Cg haloalkenyl; C2*Cg alkynyl; CpCg alkylthio; CpC6 haloalkylthio; CrC6 alkylsulfinyl; CrC6 alkylsulfonyl; C3-C6 cycloalkyl; CrC6 alkenyloxy; C02(CrC6 alkyl); NH(CrC6 alkyl); N(CpCg alkyl)2", cyano; nitro; SiR19R20R21; or GeR19R20R21; each R10 is independently halogen; CpC4 alkyl; CpC4 haloalkyl; CpC4 alkoxy; nitro; or cyano; R14 is H; halogen; CpCg alkyl; CpCg haloalkyl; C2-Cg alkenyl; C2*Cg haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; or C3-C6 cycloalkyl; Rl9t R^O ^ r21 ^ each independently CpCg alkyl; C2~Cg alkenyi; CpC4 alkoxy; or phenyl; each R25 is independently CpC4 alkyl; CpC4 haloalkyl; C2-C4 alkenyl; CpC4 alkoxy; or phenyl; and m is 0, 1 or 2.

14. The compound of Claim 13 which is selected from the group: 2,4-dihy dro-4-(2-hvdroxy pheny l)-5 -methoxy-2-methy 1-3//- l,2,4-triazol-3-one; 2,4-dihydro-4-(2-hydroxy-6-methyIphenyl)-5-methoxy-2-methy 1-3//-1,2,4-triazol-3-one; 5-chloro-2v4-dihydro-4-(2-hydroxy-6-methylphenyl)-2-methyl-3/f-l,2,4-triazol-3-one; and 5-chloro-2,4-dihydro-4-(2-hydroxyphenyl)-2-methyl-3/M,2,4-triazol-3-one.

15. A method of claim 1 for controlling arthropods which method is substantially as herein described with reference to any one of the Examples.

16. A compour.d of any one of claims 2 to 9 or claims 13 or 14, substantially as herein described with reference to any one of the Examples.

17. A fungicidal composition of claim 10, substantially as herein described with reference to any one of the Examples.

18. An arthropodicidal composition of claim 11, substantially as herein described with reference to any one of the Examples. INTELLECTUAL PROPERTY OFFICE 5/7/9fcpop5s2.si(jp- 2 2 FEB 1999 RECEIVED -203-

19. A method of claim 12 for controlling plant diseases caused by fungal plant pathogens which method is substantially as herein described with reference to any one of the following Examples. DATED this 11th day of February, 1999. E.I. DU PONT DE NEMOURS AND COMPANY By their Patent Attorneys: CALLINAN LAWRIE end of clams </div>