MXPA99001173A

MXPA99001173A - Arthropodicidal and fungicidal cyclic amides

Info

Publication number: MXPA99001173A
Application number: MXPA/A/1999/001173A
Authority: MX
Inventors: Frederick Mccann Stephen; James Brown Richard; Paul Walker Michael; Mingtak Chan Dominic; Alan Clark David; Eugene Drumm Joseph Iii; Michael Koether Gerard; Padgett Rorer Morris; Paul Selby Thomas
Original assignee: James Brown Richard; Mingtak Chan Dominic; Alan Clark David; Eugene Drumm Joseph Iii; Ei Du Pont De Nemours And Company; Michael Koether Gerard; Frederick Mccann Stephen; Padgett Rorer Morris; Paul Selby Thomas; Paul Walker Michael
Priority date: 1996-08-01
Filing date: 1999-02-01
Publication date: 2000-01-01

Abstract

Compounds of Formula (I), and their N-oxides and agriculturally suitable salts, are disclosed which are useful as fungicides and arthropodicides, wherein A is O;S;N;NR5;or CR14;G is C or N;provided that when G is C, then A is O, S or NR5 and the floating double bond is attached to G;and when G is N, then A is N or CR14 and the floating double bond is attached to A;W is O;S;NH;N(C1-C6alkyl);or NO(C1-C6alkyl);X is OR1;S(O)mR1;or halogen;R1 is C1-C6alkyl;C1-C6haloalkyl;C2-C6alkenyl;C2-C6haloalkenyl;C2-C6alkynyl;C2-C6haloalkynyl;C3-C6cycloalkyl;C2-C4alkylcarbonyl;or C2-C4alkoxycarbonyl;R2 is H;C1-C6alkyl;C1-C6haloalkyl;C2-C6alkenyl;C2-C6haloalkenyl;C2-C6alkynyl;C2-C6haloalkynyl;C3-C6cycloalkyl;C2-C4alkylcarbonyl;C2-C4alkoxycarbonyl;hydroxy;C1-C2alkoxy;or acetyloxy;m is 0, 1 or 2;and E, R5, Y, Z and R14 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (I) and a method for controlling plant diseases caused by fungal plant pathogens which involves applying an effective amount of a compound of Formula (I). Also disclosed are compositions containing the compounds of Formula (I) and a method for controlling arthropods which involves contacting the arthropods or their environment with an effective amount of a compound of formula (I).

Description

CYTOTIC AMIDAS ARTOPRODICIDAS Y FUNGICIDAS BACKGROUND OF THE INVENTION This invention relates certain cyclic amides, their N-oxides, salts and agriculturally suitable compositions as well as methods for their use as fungicides and arthropodicides. The control of plant mortality caused by pathogens of fungal plants is extremely important to achieve a highly efficient crop. The damage in the mortality to crops of fruits, cereals, ornamental vegetables and of field can cause a significant reduction in the productivity with which results in an increase in the costs for the consumers. The control of arthropod pests is extremely important to achieve a highly efficient crop. Arthropod damage to the growth and agronomic storage of crops can cause a significant reduction in productivity which results in an increase in costs to the consumer. The control of arthropod pests in forestry in ornamental crops, nurseries, greenhouses, food storage, fiber products, livestock, and public and animal health is also important. A lot of products . They are commercially available for these purposes, but the need continues for new compounds which are more effective, less expensive, less toxic, safer to the environment or have different modes of action.

BRIEF DESCRIPTION OF THE INVENTION This invention is directed to compounds of Formula I which include all stereoisomers and geometries, N-oxides and agriculturally suitable salts, agricultural compositions containing them and their use as fungicides and arthropodicides: I wherein E is selected from: i) 1, 2-phenylene optionally substituted with one of R3, R4 or both R3 or R4; ii) a naphthalene ring, provided that when G and Y are linked to the same ring, then G and Y are linked to adjacent ring members, the naphthalene ring optionally substituted with one of R3, R4 or both R3 and iii) a ring system selected from. a monocyclic provided with 5 to 12 members and systems fused aromatic heterocyclic rings bicyclic, each heterocyclic ring system contains from 1 to 6 héteroáto os independently selected from nitrogen, oxygen and sulfur group, provided that each heterocyclic ring system contains no more of 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfides, each bicyclic ring system fused optionally contains one ring. non-aromatic which optionally contains 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 members of an adjacent ring, each system of aromatic heterocyclic rings are 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 0, 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; that; S; NH; N (C 1 -C 6 alkyl); or NO (alkyl C? -C6); X is OR1; S (0) m R1; Ó halogen; R1 is Ci-Cß alkyl; C6-C6 haloalkyl; C2-C2 alkenyl C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl C3-C6 cycloalkyl; to the C2-C4 ilcarbonyl; or alkoxycarbonyl C2-C4; R2 is H; is C? -C6 alkyl; C6-C6 haloalkyl; C2-C6 haloalkenyl, C2-C6, "C2-C6, 'C2-C6 haloalkynyl C3-C6 alkylcarbonyl, C2-C; C2-C4 alkoxycarbonyl; hydroxy; alkoxy or acetyloxy -C2 C;? R3 and R4 may be independently halogen, cyano, nitro, hydroxy, d-C6 alkyl; C6 haloalkyl C;? C2-C6 haloalkenyl, C2-C6 alkynyl C-C6 haloalkynyl, C2-C, alkoxy Ci-SCs; Ci-Ce haloalkoxy; C2-C6 alkenyloxy; C2-C2 alkynyloxy; Ccy-C6 alkylthio; Cys-C6-alkylsulfinyl; C12-alkylsulfonyl;; formyl; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; NH2C (0); alkyl (C1-C4) NHC (O); (C 1 -C 4 alkyl) 2NC (0); Yes (R25) 3; Ge (R25) 3; (R25) Si-C = C-; or phenyl, phenylethyl, benzoyl or phenylsulfonyl, each substitution with R8 and optionally substituted with 1 or more R10; or when E is 1,2-phenylene and R3 and R4 are bonded to adjacent atoms, R3 and R4 can be taken together as C-C5 alkylene, C3-C5 haloalkylene, C3-C5 alkenylene or C3-C5 haloalkenylene each optionally substituted with 1-2 C 1 -C 3 alkyl; R5 is H; is C? -C6 alkyl; C6-C6 haloalkyl; C2-C6 alkenyl C2-C2 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; or C2-C4 alkoxycarbonyl; And it's -0-; -S (0) n-; -NR15-; -C (= 0) -; -CH (OR15) -; -CHR6-; -CHRdCHR6 -; - 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) -; - CHR15OC (= 0) N (R15) -; -CHR15OC (= S) N (R15) -; CHR15OC (= 0) 0-; -CHR150C (= S) 0-; -CHR150C (= 0) S-; -CHR15OC (= S) S-; -CHR15SC (= 0) N (R15) -; -CHR15SC (= S) N (R15) -; -CHR15SC (= 0) 0-; -CHR15SC (= S) 0-; -CHR15SC (= 0) S; -CHR15SC (= S) S-; -CHR15SC (= NR15) S -; - CHR15N (R15) C (= 0) N (R15) -; -CHR15C ~ 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) -; -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-; -0-CH2CH20-N = C (R7) -; -CHR150-C (R15) = C (R7) -; -CHR150-C (R7) = N-; -CHR1 S-C (R7) = N-; -C (R7) = N-NR15-; -CH = N-N = C (R7) -; -CHR15N (R15) -N = C (R7) -; -CHR15N (C0CH3) -N = C (R7) -; -OC (= S) NR15C (= 0) -; CHR6-C (= 1) -A1-; -CHR6CHR6-C (= WX) -A1-; CR6 = CR6-C (= W * -) -A1-; -C = C-C (= X) -A1-; -N = CR6-C (= W1) -A1-; or a direct link; and the directionality of the link Y is defined in such a way that the radical labeled on the left side of the link is linked to E and the radical on the right side of the link is linked to Z; Z1 is H or -A3-Z2; W1 is O or S; A1 is O; S; NR15; or a direct link; A2 is O; NR15 or a direct link; A3 is -C (= 0) -; -S (0) 2-; or a direct link; Z2 is selected from: i) C1-C10 alkyl; C2-C6O alkenyl, and C2-C2 alkynyl, each optionally substituted with one or more R10; ii) C3-Cs cycloalkyl, C3-C8 cycloalkenyl, and phenyl, each optionally substituted with one or more R10; iii) a selected ring system consisting of systems of 3 to 14 monocyclic, fused bicyclic and non-aromatic tricyclic heterocyclic fused rings and systems of 5 to 14 monocyclic members, fused bicyclics and fused aromatic tricyclic heterocyclic rings, each ring system heterocyclic contains from 1 to 6 heteroatoms independently selected from the group of 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 sulfides, each ring system aromatic and non-aromatic heterocyclics are optionally substituted with 1 or more R10; iv) a system of selected multicyclic rings consisting of systems of 8 to 14 bicyclic-fused members and tricyclic-fused rings which are a carbocyclic aromatic ring system, a non-aromatic carbocyclic ring system, or a ring system containing one or two non-aromatic rings which 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 ring as aromatic carbocyclic rings, each ulticyclic ring system optionally substituted with 1 or more R10; and v) adamantyl optionally substituted with one or more R10; each R6 is independently H; 1-2 CH3; C2-C3 alkyl; C 1 -C 3 alkoxy; C3-C6 cycloalkyl; formylamino; C2-C4 alkylcarbonylamino; C2-C4 alkoxycarbonylamino; NH2C (0) NH; (C 1 -C 3 alkyl) NHC (O) NH; (C 1 -C 3 alkyl) 2 NC (0) NH; N (C 1 -C 3 alkyl) 2; piperinidyl; morpholinyl; 1-2 halogen; cyano; or nitro; each R7 is independently H; Ci-Cß alkyl; C6-C6 haloalkyl; Ci-Cβ alkoxy; haloalkoxy C? -C6; alkylthio C? -C6; alkylsulfinyl C? -C6; alkylsulfonyl CI-CT; haloalkylthio C? -C6; haloalkylsulfinyl C? -C6; haloalkylsulfonyl C? -C6; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; C2-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy; Not me; NH (C 1 -C 6 alkyl); N (C 1 -C 6 alkyl) or morpholinyl; Z is selected from: i) C3-C8 cycloalkyl / cycloalkenyl C-Cs and phenyl, each substituted with R9 and optionally substituted with 1 or more R10; ii) a ring system selected systems consisting of 3 to 14 monocyclic members, fused bicyclic and fused, heterocyclic ring tricyclic nonaromatic and systems consisting of 5 to 14 monocyclic members, fused bicyclic and fused, heterocyclic ring tricyclic aromatic, 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 sulfides, each system of aromatic and non-aromatic heterocyclic rings substituted with R9 and optionally substituted with 1 or more R10; iii) a system of multicyclic rings selected systems 8 to 14 bicyclic-fused and ring member tricyclic-fused which are a set of aromatic carbocyclic rings, a set of non-aromatic carbocyclic ring or ring system containing one or two non-aromatic rings which 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 ring as aromatic carbocyclic rings, each system of multicyclic ring substituted with R9 and optionally substituted with one or more R10; iv) adamantyl substituted with R 9 and optionally substituted with one or more R 10; each Q is independently selected from -CHR13-, NR13 -, - 0- and -S (0) p-; R8 is H; 1-2 halogen; C C-C6 alkyl; C6-C6 haloalkyl; C6-C6 alkoxy; Ci-Cß haloalkoxy; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C? -C6 alkyl; haloalkitium Ci-Ce; alkylsulfinyl Ci-Cß; alkylsulfonyl C? -C0; C3-C6 cycloalkyl; C3-C6 alkenyloxy; C02 (Ci-C6 alkyl); N (C1-C6 alkyl) 2; cyano; nitro; SiR19R20R21; or GeR19R20R21; R9 is C? -C6 alkyl substituted with 2-3 C? -C3 alkoxy; C2-C4 alkynyl substituted with a hydroxy or 1-3 C1-C4 alkoxy; C2-C6 haloalkynyl; C3-C6 cycloalkyl substituted with a select member of 1-4 halogen, 1-2 C1-C3 alkyl, 1-2 C1-C3 alkoxy and a Z3; C3-C6 cycloalkenyl or C3-C6 cycloalkoxy each optionally substituted with a select member of 1-2 halogen, 1-2 C1-C3 alkyl, 1-2 Ci-C3 alkoxy and a Z3; adamantyl; C2-C6 alkoxyalkyl; Cilt-C6 alkylthioalkyl; C2-C6 cyanoalkyl; C3-C6 alkoxyalkynyl; tetrahydropyranyloxyalkynyl C7-C10; C1-C3 alkoxy substituted with cyano; , C (= 0) R26 or C (= 0) N (R26) 2; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy; haloalkynyloxy C3-C6; C2-C6 alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; C 1 -C 3 alkyl substituted with cyano, C (= 0) OR 26 or C (= 0) N (R 26) 2; haloalkylsulfinyl C? -C6; haloalkylsulfonyl Ci-Cg; C3-C6 alkenylthio; C3-Cß haloalkenylthio; C3-C6 alkynylthio; haloalkynylthio C3-C6; C2-C6 alkoxyalkylthio; C2-C6 alkylthioalkylthio; thiocyanate; hydroxy; mercapto; Not me; N (R26) (R28); SiR22R23R24; GeR22R23R24; (R25) 3Si-C = C-; OSi (R25) 3; OGe (R25) 3; C (= 0) R29; C (= S) R26; C (= 0) OR30; C (= S) OR26; C (= 0) SR26; C (= S) SR26; C (= 0) N (R26) 2; C (= S = N (R26) 2; C (= NR26) OR27; OC (= 0) R26; OC (= S) R26; SC (= 0) R26; C (= S) R26; N (R26) C = 0) R26; N (R26) C (= S) R26; OC (= 0) OR27; OC (= 0) S R27; OC (= 0) N (R26) 2; SC (= 0) OR27; SC (= 0) SR27; S (0) 20 R26; S (0) 2N (R26) 2; OS (0) 2R27, or N (R26) S (0) 2R27 or R9 is benzyloxy, benzyloxymethyl, phenylethynyl, phenoxymethyl, phenylthio, phenylsulfonyl, benziniltio, pyridinylmethyl, piridinilmetiloxi, piridiniloximetil, pyridinylethynyl, pyridinylthio, thienyl ethyl, thienylthio, furanylmethyl, furanyloxy, furanylthio, pyrimidinylmethyl or piididylthio, each optionally substituted on the aromatic ring with one of R11, R12, or both R11 and R12; R9 is alkyl or C2-C6 or C2-C6 alkoxy substituted with 1-2 phenyl, naphthalenyl, phenoxy, benzyloxy, pyridinyl, pyrimidinyl, thienyl, furanyl or each aromatic ring optionally substituted with one of R11, R12, R11 or both and R12; or R9 is -A4-Z4; Each R10 is independently halogen; C 1 -C 4 alkyl optionally substituted with 1-3 C 1 -C 3 alkoxy; haloalkyl C? -C4; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; haloalkinyl C2-C6; C3-C6 cycloalkyl; C2-C6 alkoxyalkyl; C2-C6 alkylthioalkyl; C2-C6 cyanoalkyl; alkoxyalkynyl C3-C6; tetrahydropyranyloxyalkynyl C7-C10; benzyloxymethyl; C4-C4 alkoxy; haloalkoxy C? -C4; C3-C6 alkenyloxy; C3-C6 haloalkenyloxy; C3-C6 alkynyloxy, - haloalkynyloxy C3-C6; C3-C6 cycloalkoxy; C2-C6 alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; C 1 -C 4 alkylthio; haloalkitium C? -C4; C 1 -C 4 alkylsulfinyl; haloalkylsulfinyl C1-C4; C 1 -C 4 alkylsulfonyl; haloalkylsulfonyl C? -C4; C3-C6 alkenylthio; C3-C6 haloalkenithium; C3-C6 alkynylthio; haloalkenylthio C-C6; C2-C6 alkoxyalkylthio; C2-C6 alkylthioalkylthio; nitro; cyano; thiocyanate; hydroxy; mercapto; N (R26) 2; SF5; Yes (R25) 3; Ge (R25) 3; (R25) 3Si-C = C-; OSi (R25) 3; OGe (R25) 3; - C (R18) = NOR17; C (= 0) R26; C (= S) R26; C (= 0) OR26; C (= S) OR26; C (= 0) SR26; C (= S) SR26; C (= 0) N (R26) 2; OC (= S) N (R26) 2; C (= N R26) 0 R27; 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; OC (= 0) N (R26) 2; SC (= 0) OR27; SC (= 0) SR27; S (0) 20 R26; S (0) 2N (R26) 2: OS (O) 2 R27; N (R26) S (0) 2 R27; or phenyl, benzyl or phenoxy, each optionally substituted on the phenyl ring with one of R11, R12, or both R11 and R12; When Y and a R10 are joined to adjacent atoms in Z and Y is -CHR150-N = C (R7) -, -0-N = C (R7) -, -0-CH2CH20-N = C (R7) - , - CHR150-C (R15) = C (R7) -, -CH = NN = C (R7) -, -CHR15N (R15) -N = C (R7) - O -CHR 15N (COCH3) -N = C (R7) -, R7 and the above-mentioned adjacent junction R10 can be taken simultaneously as - (CH2) r-J- similarly J is linked to Z; J is -CH2-; -CH2CH2 -; - OCH2-; -CH20-; -SCH2-; -CH2S-; N (R16) CH2_; or -CH2N (R16) -; each CH2 group of J mentioned above is optionally substituted with 1 to 2 CH3; Z3 is phenyl, naphthalenyl, l-pyrrolyl, furanyl, thienyl, 1H-pyrazolyl, l-imidazolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, liT-1, 2, 3-triazolyl, 2if-l, 2,3-triazolyl, lii-1,2,4-triazolyl, 4H-1,2,4-triazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1, 2, 5-oxadiazolyl, 1,3,4- oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, l-tetrazolyl, 2H-tetrazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1, 3, 5-triazinyl, 1, 2,4-triazinyl, or 1,2,4,5-tetrazinyl, each optionally substituted with one of R11, R12, or both R11 and R12; A4 is O; S; open chain or Ci-Cβ alkylene branch, or a direct bond; Z4 is selected from: i) L-pyrrolyl, L-pyrazolyl, L-imidazolyl, isozazolyl, oxazolyl, isothiazolyl, thiazolyl, 1H-1,2,3-triazolyl, 2H-1,2,3-triazolyl, lf-1 , 2,4-triazolyl, 4H-1,2,4-triazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1, 2, 5-oxadiazolyl, 1, 3, 4-oxadiazolyl, 1, 2, 3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 2, 5-thiadiazolyl, 1, 3, 4-thiadiazolyl, l-tetrazolyl, 2H-tetrazolyl, pyridazinyl, pyrazinyl, 1,3,5-triazinyl, 1, 2, 4-triazinyl, and 1, 2, 4, 5-tetrazinyl, each optionally substituted with one of R11, R12, or both R11 and R12; ii) a ring system selected from a system of 3 to 14 members monocyclic, bicyclic fused and of heterocyclic tricyclic non-aromatic fused rings and systems of 8 to 14 bicyclic-fused members and fused aromatic tricyclic heterocyclic rings, each heterocyclic ring system contains from 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen and sulfur, provided each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfides, each aromatic heterocyclic ring system and non-aromatic optionally substituted with one of RX1, R12 or both R11 and iii) a multi-ring system selected from a system of 8 to 14 bicyclic-fused members and tricyclic-fused rings which are a system of aromatic carbocyclic rings, a system of non-aromatic carbocyclic rings, or a ring system containing one or two ani non-aromatic derivatives which 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 ring as carbocyclic aromatic rings, each ring system optionally multicrystalline replaced with one of R11, R12, or both R11 and R12; each R11 and each R12 is independently 1-2 halogen; alkyl C? -C; haloalkyl C? -C; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; haloalkinyl C2-C6; C2-Cß alkoxyalkyl; C2-Cß alkylthioalkyl; C3-C6 alkoxyalkynyl; C7-C10 tetrahydropyranyloxyalkynyl, benzyloxymethyl; C4-C4 alkoxy; haloalkoxy C? ~ C4; C3-C6 alkenyloxy; C-C6 haloalkenyloxy; C3-C6 alkynyloxy; C3-C6 haloalkynyloxy; C2-C6 alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy; C2-C6 alkylthioalkoxy; C 1 -C 4 alkylthio; haloalkitium C? -C; alkylsulfinyl C? ~ C; haloalkylsulfinyl C? ~ C4; C 1 -C 4 alkylsulfonyl; haloalkylsulfonyl C? -C; C3-C6 alkenylthio; C3-C6 haloalkenylthio; C2-C6 alkylthioalkylthio; nitro; cyano; thiocyanate;hydroxy; mercapto; N (R26) 2; SF5; Yes (R25) 3; Ge (R25) 3; (R25") 3Si-C = C-; OSÍ (R25) 3; OGe (R25) 3; C (= 0) R26; C (= S) R26; C (= 0) OR26; C (= S) OR26; C (= 0) SR26; C (= S) SR26; C (= 0) N (R26) 2; C (= S) N (R26) 2; OC (= 0) R26; 0C (= 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) OR27; SC (= 0) SR27; S (0) 2OR26; S (0) 2N (R26) 2: 0S (0) 2 R27; N (R2) S (0) 2 R27; or phenyl, phenoxy, benzyl, benzyloxy, phenylsulfonyl, phenylethynyl, or pyridinylethynyl, each optionally substituted on the aromatic ring with 1-2 independently selected groups of halogens, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, haloalkoxy C? ~ C4, nitro and cyano; each R13 is independently H; C C-C6 alkyl; C6-C6 haloalkyl; or phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C alkoxy; C1-C4 haloalkoxy, nitro or cyano; R14 is H; halogen; alkyl C? _C6; C6-C6 haloalkyl; C2-C6 alkenyl; haloalkenyl C2_C6; C2_C6 alkynyl; halbalquinyl C2-Cß, or C3-C6 cycloalkyl, 'Each R15 is independently H; alkyl C? _C; C-Cd cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano; or - When Y is -CHR1SN = C (= 0) N (R15) -, the two R15 attached to nitrogen atoms of the aforementioned group can be taken simultaneously as - (CH2) S-; or when Y is -CHR150-N = C (R7) NR15-, R7 and adjacently the junction R15 can be taken simultaneously as -CH2- (CH2) S-; -0- (CH2) s-; -S- (CH) ß; 0-N (alkyl dC3) - (CH2) S-; with the directionality of the aforesaid bond defined such that the radical labeled on the left side of the bond is bonded to the carbon and the radical on the right side of the bond is bonded to the nitrogen; R16, R17 and R18 are each independently H; C1-C3 alkyl; C3-C6 cycloalkyl, "or phenyl optionally substituted by halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl / C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano; R 19, R 20, R 21, R 22, and R 23 are each independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 2 alkenyl, C 1 -C 6 alkoxy or phenyl, R 24 is C 1 -C 4 haloalkyl, each R 25 is independently C 1 -C 4 alkyl, haloalkyl C 1 -C 4; C2-C4 alkenyl; C4-C4 alkoxy; or phenyl; Each R26 is independently H; alkyl C? _C6; haloalkyl C? _C6; 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 1-2 groups independently selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro and cyano; Each R27 is independently alkyl CI-CT * haloalkyl C? -C6; C2_C6 alkenyl; haloalkenyl C2_C6; C2_C6 alkynyl; C2-C6 haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with 1-2 groups independently selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro and cyano; Each R28 is independently haloalkyl C? -C6; C2-C6 alkenyl; C-C6 haloalkenyl; C2-C6 alkynyl; haloalkynyl C2_C6; C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with 1-2 groups independently selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro and cyano; Each R29 is H; C C-C6 alkyl; haloalkyl C? _C6; C2-Cß alkenyl; haloalkenyl C2_C6; C2_C6 alkynyl; haloalkynyl C2_C6; C3_C6 cycloalkyl, "or benzyl, optionally substituted on the phenyl ring with 1-2 groups independently selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro and cyano; Each R30 is H, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl; C3_C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with 1-2 groups independently selected from halogen, *} C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro and cyano; m, n and p are each independently 0, 1 or 2; r is 0 or 1; and s is 2 or 3; as Y is -CH (OR15) -, -CHR6- -CHR6CHR6-, -CR6 = CR6-, -C = C-, -CHR150-, OCHR15-, -S (0) NCHR15, - (R7) C = N -OCH (R15) -, -CHR150-N = C (R7) -CH20-, -CHR150-C (R15) = C (R7) -, -CHR6-C (= 1) -A1-, -CHR6CHR6-C (= 1) -A1-, -CR6 = CR6-C (= WX) -A1- or -C = C-C (= W) * •) -A1-, therefore Z can be as phenyl, furanyl, thienyl, pyridinyl and pyrimidinyl.

DESCRIPTION OF THE INVENTION In the above, the term "alkyl", used either alone or in compounds referred to as "alkyl lithium" or "haloalkyl" includes open chains or branches such as the isomers methyl, ethyl, n-propyl, i-propyl, or different butyl, pentyl, or hexyl. The term "1-2 CH3" indicates that the substituent may be methyl or, when there is a hydrogen attached to the same atom, the substituent and said hydrogen may both be methyl. The term "1-2 alkyl" indicates that one or two of the available positions for that substituent may be the alkyl which are independently selected. The "alkenyl" includes open chains or branches of alkenes such as the vinyl isomers, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. He "alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. The "alkynyl" includes open chains or branches of alkynes such as the isomers ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. The "alkynyl" may also include radicals comprising multiple triple bonds such as 2,5-hexadinyl. "Alkylene" denotes open chains (or branches when indicated) alknediyl. Examples of "alkyls" include CH2CH2, CH (CH3), CH2CH2CH2, CH2CH (CH3), CH2CH2CH2CH2, and CH2CH2CH2CH2CH2. "Alkenylene" denotes an open alkenediyl chain containing an olefinic linkage. Examples of some "alkenylenes" include CH2CH = CH, CH2CH2CH = CH, CH2CH = CHCH2 and CH2CH = CHCH2CH2. The "alkoxy" includes for example the following isomers methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and -hexyloxy isomers. The term "1-3 alkoxy" indicates that 1 to 3 of the appropriate positions for that substituent may be the alkoxy which is independently selected, and the term "1-2 alkoxy" is defined analogously. The "alkoxyalkyl" denotes a substitution of the alkoxy in the alkyl. Examples of the alkoxyalkyl include the CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. He "alkoxyalkoxy" denotes a substitution of the alkoxy in the alkoxy. "Alkenyloxy" includes open chains or portions of alkenyloxy branches. Examples of alkenyloxy include H2C = CHCH20, (CH3) 2C = CHCH20, (CH3) CH = CHCH20, (CH3) CH = C (CH3) CH20 and CH2 = CHCH2CH20. He "alkynyloxy" includes open chains and portions of alkynyloxy branches. Examples of "alkynyloxy" include HC = CCH20, CH3C = CCH20 and CH3C = CCH2CH20. "Alkylthio" includes branching or portions of open alkylthio chains such as the methylthio, ethylthio isomers, and the various propylthio, butylthio, pentylthio and hexylthio. The "alkylthioalkyl" denotes an alkylthio substitution in an alkyl. Examples of "alkylthioalkyl" include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. "Alkylthioalkylthio" denotes a substitution of an alkylthio in an alkylthio. Analogously, "alkoxyalkylthio" denotes an alkoxy substitution in an alkylthio and "alkylthioalkoxy" denotes a -alkylthio substitution in an alkoxy. "Alquisulfinil" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH3S (0), CH2CH2S (0), CH3CH2CH2S (0), (CH3) 2CHS (0) and the different isylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. Examples of "alkylsulfonyl" include CH3S (0) 2, CH2CH2S (0) 2, CH3CH2CH2S (0) 2, (CH3) 2CHS (0) 2 and the different butylsulfonyl, pentisulfonyl and hexylsulfonyl isomers. He "cyanoalkyl" denotes an alkyl group substituted with a cyano group. Examples of "cyanoalkyl" include NCCH2, NCCH2CH2 and CH3CH (CN) CH2. "Alkenylthio", "alkoxyalkynyl" are defined analogously in the above Examples. The "cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "cycloalkoxy" includes the same groups attached through an oxygen atom such as cyclopentyloxy and cyclohexyloxy. The "cycloalkenyl" includes groups such as cyclopentyl, cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1,4-cyclohexadienyl. The "trialkylsilylalkoxyalkoxy" denotes a substitution of the trialkylsilylalkoxy and the alkoxy. Examples of "trialkylsilylalkoxyalkoxy" include for example a (CH3) 3SiCH2CH2OCH20. The term "1-2 phenyl" indicates that one or two of the suitable positions for such substituent - may be phenyl. The term "aromatic carbocyclic ring system" fully includes aromatic carbocycles and carbocycles wherein at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the Hückel rule is satisfied). The term "non-aromatic carbocyclic ring system" fully denotes the saturated carbocycles as well as some or all of the unsaturated carbocycles where the Hückel rule is not satisfied by any of the rings in the ring system. The term "aromatic heterocyclic ring system" fully includes aromatic heterocycles and heterocycles wherein at least one of the rings of the polycyclic ring system is aromatic (where aromatic indicates that the Hückel rule is satisfied). The term "non-aromatic heterocyclic ring system" fully denotes the saturated heterocycles as well as a part or all of the unsaturated heterocycles in which the Hückel rule is not satisfied by any of the rings of the ring system. The heterocyclic ring system can be attached through any available carbon or nitrogen by the replacement of a hydrogen in said carbon or nitrogen. A skill in this science will appreciate that not all nitrogen containing heterocycles can form N-oxides since nitrogen requires a single pair available for oxidation of the oxide; A skill in this science will recognize those nitrogens that contain heterocycles which can form N-oxides. Another skill in this science will also recognize that tertiary amines can form N-oxides. The synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic acid and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, hydroperoxide alkyl such as t-butyl hydroperoxide, sodium perborate and dioxiranes such as dimethydioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T.L. Gilchrist in Comprehensive Organic Synthesis, vol.7, pp 748-750, S.V.Ley, Ed., Pergamon Press; M.Tisler and B. Stanovnik in Comprehensive Héterociclic Chemistry, vol.3, pp. 18-20, A.J. Boulton and A. McKillope, Eds., Pergamon Press; M.R. Grimmett and B.R.T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A.R. Katritzky, Ed., Cademic Press; M. Tisler and B. Stanovnik in Advances in Héterociclic Chemistry, vol.9, pp 285-281, A.R. Katritzky and A.J. Boulton, Eds., Academic Press., And G. .H. Cheeseman and E.S.G. erstiuk in Advances in Héterociccic Chemistry, vol.22, pp 390-392, A.R. Katritzky and A.J. Boulton, Eds., Academic Press. The term "halogen", whether only in compounds such as "haloalkyl", include fluorine, chlorine, bromine or iodine. The term "1-2 halogen" indicates that 1 or 2 of the available positions for that substituent may be a halogen which is independently selected. In addition, when a compound such as "haloalkyl" is used said alkyl may be partially or fully substituted with halogen atoms which may be different or the same. Examples of "haloalkyl" include F3C, C1CH2, CFCH2 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, CF3G = C, CC13C = C and FCH2C = CCH2. Examples of "haloalkoxy" include CF30, CC13CH20, HCF2CH2CH2 (O), and CF3CH20. Examples of "haloalkylthio" include CC13S, CF3S, CC13CH2S and C1CH2CH2CH2S. Examples of "haloalkylsulfinyl" include CFS (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. The total number of carbon atoms in a substituent group is indicated by the "Ci-C-," wherein the prefixes i and j are numbers from 1 to 10. For example, C 1 -C 3 alkylsulfonyl designates methylsulfonyl via propylsulfonyl. Examples of the "alkylcarbonyl" include C (0) CH3, C (0) CH2CH2CH3 and C (0) CH (CH3) 2. Examples of "alkoxycarbonyl" include CH30C (= 0), CH3CH2OC (= 0), CH3CH2CH2OC (= 0), (CH3) 2CHOC (= 0) and the different butoxy- or pentoxycarbonyl isomers. In what has been said above when a compound of Formula I is composed of 1 or more heterocyclic rings, all substituents are attached to those rings through any available carbon or nitrogen by the replacement of a hydrogen in said carbon or nitrogen. When a group contains a substituent which can be hydrogen, for example R8 or R13, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. The compounds of this invention can exist as one or more stereoisomers. The many stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skill in this science will appreciate that a stereoisomer may be more active and / or may exhibit beneficial effects when it is enriched relatively from another stereoisomer (s) or when it is separated from another stereoisomer (s). Additionally, it is known how to selectively separate, enrich, and / or prepare said stereoisomers. According to the present invention this comprises selected compounds of Formula I, N-oxides and agriculturally suitable salts thereof. The compounds of this invention can be presented as a mixture of stereoisomers, individual stereoisomers or as an optically active form. Salts of the compounds of the invention include acid-addition salts with organic or inorganic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salysilic, Tartaric, 4-toluenesulfonic or valeric. The salts of the compounds of the invention also include those forms with organic bases (e.g., pyridine, ammonium or triethylamine) or inorganic bases (e.g., hydrates, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group as for example a phenol. The selected compounds for reasons of a better activity and / or ease of synthesis are: Selection 1. Previous compounds of Formula I, and N-oxides and agriculturally suitable salts thereof, wherein: E is selected from the group 1, 2-phenylene; 1,5-, 1,6-, 1,7-, 1,8-, 2,6-, 2,7-, 1,2-, and 2,3-naphthalenediyl; 1H-pyrrolo-1, 2-, 2,3- and 3,4-diyl; 2,3- and 3, 4-furandil; 2,3-and 3, 4-thiofenediyl; L-pyrazoloyl, 5-, 3,4- and 4,5-diyl; 1H-imidazolo-1, 2-, 4,5- and 1,5-diyl; 3,4- and 4,5-isoxazolediil; 4, 5-oxazolediil; 3,4- and 4,5-isothiazolediyl; 4,5-thiazolediyl; 1H-1, 2, 3-triazolo-l, 5- and 4,5-diyl; 2i * i-l, 2,3-thiazolo-4,5-diyl; lii-1, 2,4-triazolo-1,5-diyl; 4H-1, 2,4-triazolo-3,4-diyl; 1, 2, 3-oxadiazolo-4,5-diyl; 1,2,5-oxadiazolo-3,4-diyl; 1, 2, 3-thiadiazolo-4,5-diyl; 1, 2, 5-thiadiazolo-3, 4-diyl; li -tetrazolo-1, 5-diyl; 2,3- and 3, 4-pyridinediyl; 3,4- and 4,5-pyridazinediil; 4, 5-pyrimidinediyl; 2, 3-pyrazinediil; 1, 2, 3-triazino-4,5-diyl; 1, 2, 4-triazino-5,6-diyl; líf-indolo-l, 4-, 1,5- 1,6, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5 -, 3.6-, 3.7-, 1,2-, 2,3-, 4,5-, 5,6-, and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl; benzo [b] thiophene-2, 4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3- , 4,5-, 5,6 and 6,7-diyl; 1H-indazolo-1, 4-, 1,5-, 1,6-, 1,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5 , 6- and 6,7-diyl; lyf-benzimidazole-1, 4-, 1,5-, 1,6-, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5 , 6- and 6,7-diyl; 1,2-, -benzisoxazolo-, 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-benzoxazolediil; 1, 2-benzisothiazolo-, 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-benzothiazolediil; 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-quinolinediil; 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-isoquinolinediil; 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-cinnolinediil; 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-quinazolinediil; 2,5-, 2,6-, 2,7-, 2,8-, 2,3-, 5,6-, 6,7-, and 7,8-quinoxalinediil; 1,8-naphthyridino-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-pteridinediil; pyrazolo [5, 1-b] thiazolo 2,6-, 2,7-, 3,6-, 3,7-, 2,3-, and 6,7-diyl; thiazolo [2, 3-c] -1, 2, 4-triazolo-2, 5-, 2,6-, 5,6-diyl; 2-oxo-l, 3-benzodioxolo-4, 5- and 5,6-diyl; 1,3-dioxo-lii-isoindolo-2,4-, 2,5-, 4,5- and 5,6-diyl; 2-oxo-2J * í-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; [1, 2, 4] triazolo [1, 5-a] pyridine-2,5-, 2,6-, 2,7-, 2,8-, 5,6-, 6,7-, and 7, 8-diyl; 3,4-dihydro-2,4-dioxo-2H-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-] tlazolo-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-quinolinediil; 2, 3-dihydro-l, 1,3-trioxo-1,2-benzisothiazolo-2, 4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-diyl; 1, 3-benzodioxolo-2, 4-, 2, 5-, 4, 5-, and 5,6-diyl; 2,3-dihydro-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5- , 5,6- and 6,7-benzofurandiyl; 2, 3-dihydro-1,4-benzodioxin-2, 5-, 2,6-, 2,7-, 2,8-, 5,6- and 6,7-diyl; and 5, 6, 7, 8-tetrahydro-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 is optionally substituted with one of R3, R4, or both R3 and R4; W is O; R 1 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl; R2 is H; C C-C6 alkyl; C6-C6 haloalkyl; C6-C6 cycloalkyl; R3 and R4 are each independently halogen; cyano; nitro; C C-C6 alkyl; haloalkyl Ci-Ce; C6-C6 alkoxy; haloalkoxy C? -C6; alkylthio C? -C3; C 1 -C 6 alkylsulfonyl; C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; (C1-C4 alkyl) NHC (0); (C 1 -C 4 alkyl) 2NC (O); benzoyl; or phenylsulfonyl; And it's -0-; -S (0) n-; -NR15-; -C (= 0) -; -CH (OR15) -; -CH2-; -CH2CH2-; -CH = CH-; -CSC-; -CH20-; -OCH2_; -CH2S (0) n-; - - S (0) nCH2-; -CH20-N = C (R7) -; (R7) C = N-OCH (R15) -; -C (R7) = N-0; or a direct link; R7 is H; C C-C6 alkyl; C6-C6 haloalkyl; C6-C6 alkoxy; alkylthio C? -C6; C2-C6 alkenyl; C2-C6 alkynyl; C3-C6 cycloalkyl; halogen; or cyano; When Y and R10 are joined to adjacent atoms in Z and Y is -CH2-0-N = C (R7), R7 and the aforementioned adjacent junction R10 can be taken at the same time as - (CH2) r-J- each J is joined to Z; Z is selected from the group C3-Cs, cycloalkyl, phenyl, naphthalenyl, anthracenyl; fenaltrenyl, lff-pyrrolyl; furanyl, thienyl, l-pyrazolyl, l-imidazonyl, isoxazolyl, oxazolyl; isothiazolyl, thiazolyl, 1H-1, 2, 3-triazolyl; 2H-1,2,3-triazolyl; LFI-1,2,4-triazolyl; 4H-1, 2,4-triazolyl; 1, 2, 3-oxadiazolyl; 1, 2, 4-oxadiazolyl; 1,2,5-oxadiazolyl; 1, 3, 4-oxadiazolyl; 1, 2, 3-oxadiazolyl; 1, 2, 3 thiadiazolyl; 1,2,4 thiadiazolyl; 1,2,5 thiadiazolyl; 1,3,4 thiadiazolyl; LF-tetrazolyl; 2H-tatrazolyl; pyridinyl; pyridazinyl; piri idinil; pyrazinyl; 1, 3, 5-triazinyl; 1, 2, 4-trazinyl; 1, 2, 4, 5-tetrazinyl; líf-indolyl; benzofuranyl; benzo [b] thiophenyl; li? -iindazolyl; L-benzimidazolyl; benzoxazolyl; benzothiazolyl; quinolinyl; isoquinolinyl; cinnolinil; phthalazinyl; quinazolinyl; quinoxalinyl; 1,8-naphthyridinyl; pteridinyl; 2, 3-dihydro-li? -indenyl; 1,2,3,4-tetrahydronaphthalenyl; 6, 7, 8, 9-tetrahydro-5iY-benzocycloheptenyl; 5, 6 ', 7,8,9, 10-hexahydrobenzocyclooctenyl; 2, 3-dihydro-3-oxobenzofuranyl; 1,3-dihydro-l-oxoisobenzofuranyl; 2, 3-dihydro-2-oxobenzofuranyl; 3, 4-dihydro-4-oxo-2iT-l-benzopyranyl; 3, 4-dihydro-l-oxo-lH-2-benzopyranyl; 3, 4-dihydro-3-oxo-l.ff-2-benzopyranyl; 3, 4-dihydro-2-oxo-2i? -l-benzopyranyl; 4-oxo-4-l-benzopyranyl; 2-oxo-2 # -l-benzopyranyl; 2,3,4,5-tetrahydro-5-oxo-l-benzoxepinyl; 2,3,4,5-tetrahydro-2-oxo-l-benzoxepinyl; 2, 3-dihydro-l, 3-dioxo-lH-isoindonyl; 1,2,3,4-tetrahydro-l, 3-dioxoisoquinolinyl; 3, 4-dihydro-2,4-dioxo-2H-l, 3-benzoxazinyl; 2-oxo-l, 3-benzodioxolil; 2, 3-dihydro-1,3,1-trioxo-1,2-benzisothiazolyl; 9T-fluorenil; azulenil; and thiazolo [2, 3-c] -1, 2,4-triazole; each group substituted with R9 and optionally substituted with one or more R10; and R15 is H; alkyl C? -C3; or C3-C6 cycloalkyl. Selection 2. Selection Compounds 1 where: E is selected from group 1, 2-phenylene; 1,6-, 1,7-, 1,2-, and 2,3-naphthalenediyl; 2,3- and 3, 4-furandil; 2,3- and 3, 4-thiofenedil; 2,3- and 3, 4-pyridinedil; 4,5-piri idinedil; 2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandyl and benzo [b] thiophene-2, 4-, 2, 7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-diyl; each aromatic ring system optionally substituted with one of R3, R4 or both R3 and Z is selected from the phenyl group; naphthalene; 2-thiazolyl; 1, 2, 4-oxadiazolyl; 1, 3, 4-oxadiazolyl; 1,2,4-thiadiazolyl; 1, 3, 4-thiadiazolyl; pyridinyl; and pydinyl; each group substituted with R9 and optionally substituted with one or more R10; R7 is H; Ci-Cß alkyl; haloalkyl CI-CT; Ci-Cβ alkoxy; Ci-Cß alkylthio, C2-C6 alkenyl, C2-C6 alkynyl; C3-C6 cycloalkyl; halogen; or cyano; or R 9 is cycloalkyl substituted with a minor member selected from 1-2 halogen, 1-2 C 1 -C 3 alkyl, 1-2 C 1 -C 3 alkoxy, and a Z 3; C? -C6 cycloalkyl optionally substituted with a minor member selected from 1-2 halogen, 1-2 C1-C3 alkyl, 1-2 C1-C3 alkoxy, and a Z3; haloalkylsulfinyl Ci-Ce; haloalkylsulfonyl C? -C6; thiocyanate; SiR22R23R24; GeR22R23R24; (R25) 3Si-C = C-; C (= 0) R29; C (= 0) OR30; S (0) 2N (R26) 2; OS (0) 2R27, or R9 is benzyloxy, phenylethynyl, phenoxymethyl, phenylthio, phenylsulfonyl, benzinylthio, pyridinyl ethyloxy, pyridinyloxy ethyl, pyridinylethynyl, or furanyloxy, each optionally substituted on the aromatic ring with one of R11, R12, or both R11 and R12; or R9 is C2-C6 alkyl or C2-C6 alkoxy substituted with 1-2 phenyl, naphthalenyl, phenoxy, benzyloxy, pyridinyl, pydinyl, thienyl, or furanyl, each -aromatic-ring optionally substituted with one of R11, R12, or both R11 and R12; or R9 is -A4-Z4; Each R10 is independently halogen; haloalkyl C? -C4 C2-C6 alkynyl; nitro; cyano; Yes (R25) 3; or (R25) 3Si-C = C-; or when Y and an R10 are attached to adjacent atoms in Z and Y is -CHR150-N = C (R7) -, R7 the above-mentioned adjacent junction R10 can be taken simultaneously as - (CH2) r-J- each J is joined to Z; J is -CH2-; -CH2CH2-; Z3 is phenyl, furanyl, thienyl or pyridinyl, each optionally substituted with one of R11, R12, or both R11 and R12; A4 is a direct bond Z4 is 1, 3-benzodioxolil optionally substituted with one of R11, R12, or both R11 and R12; r is 1; Selection 3. Selection Compounds 2 where: E is selected from the group of 1,2-phenylene; 2,3- and 3, 4-thiofenediyl; and 2,3- and 3, 4-pyridinediyl; each aromatic ring system optionally substituted with one of R3, R4, or both R3 and R4; A is O or N; X is OR1; R1 is C1-C3 alkyl; R 2 is H or C 1 -C 2 alkyl; - -And it's -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) -; -CH20C (= 0) NH-CH2S-C (R7) = N; or a direct link; Z is selected from the phenyl group; 2-thiazolyl; 1,2,4-thiadiazolyl; pyridinyl; and pyrimidinyl; each group substituted with R9 and optionally substituted with one or more R10; R7 is H; C1-C3 alkyl; C1-C3 haloalkyl / C? -C3 alkoxy; C1-C3 alkylthio; or cyclopropyl; and R15 is H; alkyl C? -C3; or cyclopropyl; Selection 4. Selection Compounds 3 where: R1 is methyl; R2 is methyl; And it's -0-; -CH20-; -CH20-N = C (R7) -; - (R7) C = N-OCH (R15) -; R9 is C3-C6 cycloalkyl substituted with a Z3; cycloalkoxy C3-C6; S iR22R23R24; GeR22R23R24; (R25) 3S i-C = C-; S (0) 2OR26; S (0) 2N (R26) 2, or OS (0) 2R27; or R9 is benzyloxy, pyridinyl ethyloxy, each optionally substituted on the aromatic ring with one of R11, R12, or both R11 and R12; or R9 is C2-C6 alkyl substituted with phenyl optionally substituted with one of R11, R12, or both R11 and R12; or R9 is -A4-Z4; Each R10 is independently halogen; C1-C4 haloalkyl C2-C6 alkynyl; ó Si (R25); and --Z3 is phenyl, optionally substituted with one of R11, R12, or both R11 and R12; Selection 5, Selection Compounds 4 where: Y is -0-; -CH20-N = C (R7) -; and R9 is C3-C6 cycloalkyl substituted with a Z3; cycloalkoxy C3-C6; SiR22R23R24; GeR22R23R24; or (R25) 3Si-C = -; or R9 is benzyloxy, optionally substituted on the aromatic ring with one of R11, R12, or both R11 and R12; or R9 is -A4-Z4; More preferably, they are selection compounds of the group: 4- [2- [[3- (1,3-benzodioxol-5-yl) -1,2,4-thiadiazol-5-yl] oxy] phenyl] -2 , 4-dihydro-5-methoxy-2-methyl-3-yl, 2,4-thiazol-3-one; 4- [2- [[[[1- [3- [dimethyl (3,3,3-triumphoropropyl) silyl] phenyl] ethylidene] amino] oxy] ethyl] phen yl] -2,4-dihydro-5-methoxy -2-methyl-3-l, 2,4-thiazol-3-one; 4- [2- [3- [(2-chlorophenyl) methoxy] phenoxy] phenyl] -2,4-dihydro-5-methoxy-2-methyl-3i "i-l, 2,4-thiazol-3-one; 4- [2- [[3- [1- (4-chlorophenyl) cyclopropyl] -1,2,4-thiadiazol-5-yl] oxy] phenyl] -2,4-dihydro-5-methoxy-2- methyl-3H-1,2,4-triazol-3-one; 4- [2- [[3- [1- (4-chlorophenyl) cyclopropyl] -1,2,4-thiadiazol-5-yl] oxy] phenyl] -6-2,4-dihydro-5-methoxy-2-methyl-4- [2- [[[1- [3- - - [tris (trifluoromethyl)] yl] phenyl] ethylidene] amino] oxy ] met il] phenyl] -3J? -1,2,4-triazol-3-one; and 2,4-dihydro-5-methoxy-2-methyl-4- [2- [3- [2- (trimethylsilyl ethynyl] phenoxy] phenyl] -3IT-1,2,4-triazol-3-one This invention also relates to fungicidal compositions comprising effective fungicidal amounts of the compounds of the present invention and at least one of a surfactant, a solid diluent or a liquid diluent The selected compositions of the present invention are those comprising the compounds selected above. relates a method to control the mortality in plants caused by fungal plant pathogens comprising the application of the plant or a portion of this, or for the seed of the plant or plant that has grown from seed, a fungicidally effective amount of the compounds of the invention (eg, as a composition described here). The methods selected for use are those that involve the compounds selected above. This invention also relates arthropodid compositions comprising arthropodidally effective amounts of the compounds of the present invention and at least one of a surfactant, a solid diluent or a liquid diluent. Of note are the arthropodocidal compositions of the present invention which comprise the compounds selected above. 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 the present invention (e.g., as compositions described herein). Of note are arthropodocidal methods which involve the compounds selected above. Note compounds for their arthropodicidal activity include: 4- [2- [[[[1- [3- [dimethyl (3,3,3-trifluoropropyl) silyl] phenyl] ethylidene] amino] oxy] methyl] phen il] -2,4-dihydro-5-methoxy-2-methyl-3i? -l, 2,4-triazol-3-one; 4- [2- [[3- [1- (4-chlorophenyl) cyclopropyl] -1,2,4-thiadiazol-5-yl] oxy] phenyl] -2,4-dihydro-5-methoxy-2-methyl -3H-1, 2,4-triazol-3-one; and 4- [2- [[3- [1- (4-chlorophenyl) cyclopropyl] -1,2,4-thiadiazol-5-yl] oxy] -6-methylphenyl] -2,4-dihydro-5-methoxy -2-methyl-3H-1,2,4-triazol-3-one. Of note are compounds where R9 is another thing that N (R26) (R28) and pyridinyloxymethyl; and R9 is other than C2-C6 alkyl substituted with naphthalelyl, phenoxy, benzyloxy each aromatic ring optionally substituted with 1 R11, R12 or both R11 and R12; and R9 is something other than alkoxy C2-Cd substituted with 1-2 phenyl, naphthalenyl, phenoxy, benzyloxy, pyridinyl, thienyl or furanyl, each aromatic ring optionally substituted with one of R11, R12, or both R11 and R12. The compounds of Formula 1 can be prepared by one or more of the following methods and variations as described in Scheme 1-41. The definitions of E, A, G, W, X, Rx-R30, Y, Z1-Z, W1, A1-A4, Z, Q, J, m, n, p, rys in the compounds of Formula 1- 94 below as defined above in the summary of the invention. The compounds of Formula Ia-In are sub-positioned of the compounds of Formula I, and all substituents for Formula Ia-In are defined above for Formula I. One skill will be to recognize that some compounds of Formula I may exist in a or more tautomeric forms. For example, a compound of Formula I wherein R2 is H may exist as a tautomer la or Ib or both la and Ib. The present invention comprises all tautomeric forms of Formula I.

- - Ib The compounds of Formula I can be prepared as described below in the procedures from 1) to 5). Procedures 1) to 4) describe syntheses that involve the construction of the amide ring after the formation of the aryl radical (E-Y-Z). Process 5) describes the synthesis of the aryl radical (E-Y-Z) with the amide ring already in place. 1) Alkylation procedure. The compounds of Formula I are prepared to treat compounds of Formula 1 with an appropriate alkyl transfer reagent in an inert solvent with or without adding acidic or basic reagents or other reagents (Scheme 1). Suitable solvents are selected from the group consisting of polar aprotic solvents such as acetonitrile, dimethylformamide or dimethylsulfoxide; ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.

- - I X '= OH, SH, NH2. X - OR > , SRl NH (CJ-C6 alkyl) or NH (Cj-C6 alkoxy) Method 1: U-CH-N2 (U = Hor (CH3) 3Si) 2 NH Method 2: C13C- 3 Method 3, - (R ') 3? + BF - Method 4: (R '^ SO ^; R1OS02V; orR'-hai; optional base (hal «= F, Cl, Br, orI) CV» alkyl »Cj-C6, haloalkyl C Cg 04 CH3-C6H4) For example, the compounds of Formula I can be prepared by the action of diazoalkene reagents of Formula 2 such as diazomethane (U = H) or trimethylsilyldiazomethane (U = (CH 3) 3 Si) in dicarbonyl compounds of Formula 1 (Method 1) . The 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 with Formula I can also be prepared by contacting them with carbonyl compounds of Formula I with alkyl trichloroacetimidate of Formula 3 and a catalyst - - Lewis acid. The Lewis acids include trimethylsilyl triflate and tetrafluoroboric acid. The alkyl trichloroacetimidate can be prepared from an appropriate alcohol and trichloroacetonitrile as described in the literature (J.Danklmaier and H. Hónig, Synth Commun. , (1990), 20,203). Compounds with Formula I can also be prepared from compounds of Formula 1 by treatment with a trialkyloxonium tetrafluoroborate (i.e., Meerwein salts) of Formula 4 (Method 3). The use of trialkyloxonium salts as powerful alkylate agents is very well known in the field (see U. Scholkopf, U. Groth, C. Deng, Angew. Chem., Int. Ed. Engl. , (1981), 20,798). Other alkylating agents which can convert carbonyl compounds of Formula 1 to compounds of Formula I are alkyl sulfates such as dimethyl sulfate, sulfonates such as methyl triofluoromethanesulfonate, and alkyl halides such as iodomethane and propargyl bromide (Method 4). These rentals can be conducted with or without additional base. Some suitable bases include alkali metal alkoxide such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, or tertiary amines such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec. Jan 7 (DBU), and triethylene diamine. See R.E. Benson, T.L. Cairns, J. Am.

Chem. Soc., (1948), 70, 2115, for Examples of alkylation using agents of this type. The compounds of Formula la (Formula compounds 1 where G = C, = 0 and X '= 0H) can be prepared by condensation of alonates or malonate derivatives of Formula 5 with an ambiguous nucleophile of Formula 6 (Scheme 2). The nucleophiles of Formula 6 are N-substituted hydroxylamines (HO-? HR2) and substituted hydrazines (H? (R5) -? HR2). Examples of such nucleophiles are N-methylhydroxylamine and methylhydrazine. The malonate esters of Formula 5 can be prepared by methods described above. The esters of Formula 5 can also be activated by a first hydrolysis of the ester to form the corresponding carboxylic acid, and then convert the acid to hydrochloric acid (T = C1) using thionyl chloride or oxalyl chloride, or in imidazole acyl (T = 1-imidazolyl) by treatment with 1,1 '-carbonyldiimidazole. The compounds of the laa Formula can be prepared by the reaction of nitrile esters of Formula 5b with ambient nucleophiles of Formula 6. See M. Scobie and G. Tennant, J. Chem. Soc., Chem. Comm. , (1994), 2451. Alkylation of lane with alkyl halides in the presence of a base provides - compounds of Formula Lab. Alternatively, the treatment of laa with alkylamines or alkoxyamines gives compounds of Formula Lab.

ESOUEMA 2 la = 0 < alkyl? -C41, Cl, 1- imidazole 5b iaa W = NH 0 lab HoNC alquUC! ^) = N (alquüC C6) or NO ^ lquil C [-C6) The esters of Formula 5a can be prepared by a reaction with catalyzed copper (I) of malonate esters of Formula 7 with aryl substituted halides of Formula 8 this according to the methods adopted by A. Ozuka, T. Kobayashi and H. Suzuki, Synthesis, (1983), 67 and MS Malamas, T.C. Hohman, and J. Millen, J. Med. Chem., 1994, 37, 2043-2058, and illustrated in Scheme 3. The methods for preparing the compounds of Formula 8 are described below (See Scheme 33). The malonate esters of Formula 5a can also be prepared from carboxylic acid diester of Formula 5c after modification of the carboxylic acid functional group of the appropriate group Y and Z. A coupled catalyzed copper (I) of malonates from Formula 7 with orthobromocarboxylic acids of Formula 8a (see A. Bruggink, A. McKillop, Tetrahedron, (1975), 31, 2607) can be used to prepare compounds with Formula 5c as shown in Scheme 3. Methods for preparing compounds with Formula 8a are common in this field (see P. Beack, V. Snieckus, Acc. Chem. Res., (1982), 15, 306 and Org. React., (1979), 26, 1 and references in this regard).

SCHEME 3 g Cul, base 5a R »C1-C alkyl 5c R »alkyl C 1 ^ Additionally, the malonate esters of Formula 5a can be prepared by treating the esters of acetic acid aryl of Formula 9 with an alkyl carbonate or an alkyl chloroformate in the presence of a suitable base such as, but not limited to, sodium metal or the hydride of sodium (Scheme 4). For example see J. Am. Chem. Soc., (1928), 50.2758. The nitrile esters of Formula 5b can be prepared similarly to compounds of Formula 10.

- - SCHEME 4 9 5a = alkyl Cj-Ca R = alkyl CJ-C4 The esters of Formula 9 can be prepared from the acid-catalyzed alcoholysis of the acetonitriles of Formula 10 or the etherification of the acetic acid aryl of Formula 11 as illustrated in Scheme 5 (see Org. Synth , Coll. Vol I, (1941), 270). Additionally the esters of Formula 9 can be prepared, by the cross-linking reaction with catalyst-palladium (0) of aryl iodides of Formula 8 with a Reformatsky reagent or an alkoxy (trialkyl stanil) acetylene followed by hydration (Scheme 5). For example see T. Sakamoto, A. Yasuhara, Y. Kondo, H.

- -Yamanaka, Synlett, (1992), 502, and J.F. Fauvarque, A.Jutard, J. Organometal. Chem., (1977), 132, C17. SCHEME 5 9 11 > i BrZnCH2C? 2Ror (1) R3SnC »COR Pd ° cat. (2) H + R »alkyl Cj-C4 The aryl acetic acid esters of Formula 9a can be prepared for a catalyzed copper (I) 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. FIGURE 6 12 9a R = alkyl C C < Y1 = O, S, OCHR15, SCHR15, 0-N = C (R7), NR15 - - Some esters of Formula 9 (Formula 9b) can be prepared by forming the Y2 bridge using a chemical substitution of conventional nucleophilics (Scheme 7). The displacement of an appropriate leaving group (Lg) in electrophiles of Formula 15 or 16 with a nucleophilic ester of Formula 14 provides compounds of Formula 9b A base, for example sodium hydride, is used to generate the corresponding alkoxide or thialkoxide of the compound of Formula 14. SCHEME 7 Lg- Z or 14 9b R = alkyl CJ-C4 R31-OH, SH. CHRl5OH, CHR15SH, NHR15 Y2-O, S, OCHR15, SCHR15, CHR! 50, CHR15S, NR15 Lg-Br, L OSO2CH3, OS? 2 (4-Me-Ih) Some esters of Formula 9 (Formula 9e) can be prepared by forming the Y3 bridge of the substituted 9d hydroxylamine and carbonyl compounds 14a. The hydroxylamine 9d which is in turn is prepared from esters 9c. This method has been described in EP-A-600, 835 and illustrated in Scheme 8.

SCHEME 8 9c 9C B-CHR ^ Br R "^ ^ 9d B - CHRl5ON» .Hs Y3 -CHR15ON-C (R7) 2) Addition / elimination conjugate displacement procedures. Compounds of Formula I can be prepared by the reaction of compounds of Formula 17 with alkali metal alkoxides (R 1 0"M +), alkali metal tialkoxides (R 1 S ~ M +), or an amine derivative in a suitable solvent (Scheme 9). The excess group Lg1 in the amides of Formula 17 are any group known in this field to be subjected to such a displacement reaction Examples of suitable leftover groups include bromine, chlorine and sulfonate and sulfonyl groups Examples of some solvents suitable inerts are dimethylformamide or dimethyl sulfoxide, methanol dimethoxyethane.

- - SCHEME 9 X-OR1, SR1, NH2, NHRI, N ^ lkC ^ J '. NalcoxyCi-Cg) :, or N (alkoxy q-C $) Rl Lg í - CL Br, -SQ2V, or -OSOjV, haloalkyl Cj-C? or -CH3-C6H4 M = Na The compounds of Formula 17a can be prepared from compounds of Formula Ib (compounds of Formula 1 wherein X is OH) by reaction with halogenated agents such as thionyl chloride or phosphorus oxybromide to form the corresponding β-halo-substituted derivatives. (Scheme 10). Alteranically the compounds of Formula Ib can be treated with alkylsulfonyl halides or haloalkyl sulfonyl anhydride, such as methanesulfonyl chloride, p-toluenesulfonyl chloride and the trifluoromethanesulfonyl anhydride, to form the corresponding β-alkylsulfonate of Formula 17a. The reaction with halide sulfonyl can be carried out in the presence of a suitable base (e.g., triethylamine).

SCHEME 10 I 17a Lg2 - CL Br, or-OS? 2V V «alkyl Cj-Cg, haloalkyl Cj-Cg or F ^ J ^ -Cg? Ij hal = Br, Clo: F As illustrated in Scheme 11, the sulfonyl compounds of Formula 17b can be prepared by the oxidation of the corresponding thio of Formula 18 using well-known methods for the oxidation of sulfides. (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® (KHS05). SCHEME 11 18 17b V = alkyl Cj-Cg, haloalkyl Cj-Cg or -CH3-C6H4 Alternatively the halo compounds of Formula 17c (compounds of Formula 17a wherein A = N, G = N and W = 0) can be prepared from hydrazine of Formula 19 - as illustrated in Scheme 12. When R32 = C (= S) S (alkyl) C1-C4) the diacyl compound of Formula 19 is treated with an excess of thianyl halide, for example an excess of thionyl chloride. The product formed first is the closed ring of compound of Formula 20 which can be isolated or converted in itself to the compound of Formula 17c; see P. Molina, A. Tarraga, A. Espinosa, Synthesis, (1989), 923 for a description of this process. Alternatively, when R32 = R2 as defined above, the hydrazide of Formula 19 is cyclized with phosgene to form cyclic urea of Formula 17c wherein hal = Cl. This procedure is described in detail in J. Org. Chem. (1989), 54, 1048. SCHEME 12 17c hal = Cl, Br, 1 - - The hydrazides of Formula 19 can be prepared as illustrated in Scheme 13. The condensation of the isocyanate of Formula 12 with the hydrazine of Formula H2NNR2R32 in an inert solvent such as tetrahydrofuran provides the hydrazide. SCHEME 13 R32 m C (* S) S (alkyl C! -C4) or R2 3) Addition / cyclization conjugate procedure In addition to the methods discussed above, the compounds of Formula I wherein X = SR1 and G = C (Formula le) can be prepared by the treatment by a ketenedithioacetal of Formula 22 with a nucleophilic acid of Formula 6 (Scheme 14). The nucleophiles of Formula 6 are described above.

SCHEME 14 22-R-alkyl Ci-G, - - The ketene dithioacetal of Formula 22a or 22b can be prepared by the condensation of acetic acid esters of Formula 9 or amides of Formula 9f, respectively, with carbon disulfide in the presence of a suitable base, followed by a reaction with two equivalents of a halide-R 1, such as iodomethane or propargyl bromide (Scheme 15). The conversion of 22b to 22c can be carried out by reaction with trialkyl tetrafluoroborates SCHEME 15 H2 R »alkyl CitC, 22a 9f 22o T = H, C6 alkyl, C6 alkoxy The 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 carbonyl Formula 24 (Scheme 16). Carbonylated agents of Formula 24 are carbonyl or thiocarbonyl transfer reagents such as phosgene, thiophosgene, diphosgene (C1C (= 0) 0CC13), triphosgene (C13C0C (= 0) 0CC13), N, N'-carbonyldiimidazole, N, N'-thiocarbonyldiimidazole, and the 1,1 '-carbonyldi (1, 2, 4-triazole). Alternatively, the compounds of Formula 24 may be alkyl chloroformates or dialkyl carbonates. Some of these carbonylated reactions may require the addition of a base for the reaction effect. Some suitable bases include alkoxides, alkali metal such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, tertiary amines such as triethylamine and triethylendia ina, pyridine, or 1,8-diacybicyclo [5.4.0 ] undec-7-en (DBU). Some suitable solvents include polar aprotic such as acetonitrile, dimethylformamide, or dimethyl sulfoxide, ethers such as tertahydrofuran, 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 between 0 and 150 ° C the reaction time can be from 1 to 72 hours depending on the selected base, solvent, temperature and substrate. ESOUEMA 16 23 ld T1 and T2 are independently Cl > OCCl3, 0 (alquUC? -C6), 1-imidazole, 1,2,4-thiazole X-OH or SH X ^ Oo S The N-amino-ureas of Formula 23 can be prepared as illustrated in Scheme 17. The treatment of any arylamine of Formula 25 with phosgene, thiophosgene, N, N'-carbonyldiimidazole, or N, N'-thiocarbonyldiimidazole yields the isocyanate. or isothiocyanate of Formula 26. A base can be added to the reactions with phosgene or thiophosgene. The isocyanates of Formula 26 can also be prepared by heating the acylazides of Formula 25a in a solvent such as toluene or benzene (Curtius array). The corresponding acylazides can be prepared from very well-known methods in this field (see March, J., Advanced Organic Chemistry, 3rd Edition, John Wiley: New York, (1985) pp 428,637 and also Chem. Pharm. Bull (1977) , 25,165, and references in this regard.

Subsequent treatment of iso (thio) cyanate with a substituted hydrazine R2 produces the N-amino-urea of Formula 23 SCHEME 17 NH- NH 23 Compounds of Formula I (compounds of Formula 1 wherein A = CR14, G = N, X = 0) can be prepared by any method illustrated in Scheme 18. Urea of Formula 27 react with activated 2-halocarboxylic acid derivatives such as 2-halocarboxylic acid chlorides, esters 2-halocarboxylic acid or imidazole 2-haloacyl. The acylation in the aryl amino nitrogen is followed by an intramolecular displacement of the 2-halo group for cyclization effects. A base can be added to accelerate the acylation and / or the subsequent cyclization. Some suitable bases include triethylamine and sodium hydride. Alternatively compounds of Formula can be prepared by the reaction of Formula 26 of iso (thio) cyanates of Formula 26a or carbodiimides with esters of Formula 28a. As described above, the base can be added to accelerate the reaction and the subsequent cyclization to compounds of Formula I. The carbodiimides 26a can be prepared as shown in Scheme 18, starting with compounds of Formula 26. SCHEME 18 23a 26a W = o, s W = NT5 T5 - C 1 -Cg alkyl, C 1 -C alkoxy - The (thio) ureas or amidones of Formula 27 can be prepared by either of the two methods illustrated in Scheme 19. Arylamine of Formula 25 can be contacted with an isocyanate or an isothiocyanate of Formula R2N = C = as described above. Alternatively, an iso (thio) cyanate of Formula 26 or a carbodiimide of Formula 26a can be condensed with an amine of Formula R2-NH2 to form urea or amidine. The arylamine and the iso (thio) cyanate of Formula 25 and 26, respectively, are commercially available or can be prepared by very well-known methods. For example, isothiocyanates can be prepared by methods described in J. Heterocycl. Chem., (1990), 27,407. The 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 of these. For methods where the preparation of arylamines of Formula 25 that are not commercially available are described, see M.S.Gibson in The Chemistry of the Amino Group; Patai, S., ed .; Interscience Publisher, 1968; P 37 and Tetrahedron Lett. (1982), 23 (7), 699 and references of these.

SCHEME 19 26: W «0, S 26a: W-NT5 T5 = alkyl Cj-Cg, alkoxy Cj-Cg 4) TION PROCESSES Compounds of Formula I, compounds of Formula I wherein W = S, can be prepared by treating compounds of Formula Id (I wherein W = 0) with reagents ++++ such as P2S5 or Lawesson's reagents (2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosptane-2, 4-disulfide) as illustrated in Scheme 20 (see Bull, Soc.Chim.Elg. , (1978) 87.229, and Tetrahedron Lett., (1983), 24.3815). . • SCHEME 20 Id X = O! O SR1 The reaction of compounds of Formula read with a halide alkyl in the presence of a base provides compounds of Formula leb, which can react with compounds of Formula T5NH2 and then alkylated with R2- (Br, Cl or I) to give compounds of Formula reads. SCHEME 20a read leb lee R- alkyl C C4 T5 = alkyl C? -C6, alkoxy C, -C? ) Procedure for the synthesis of the aryl radical (E-Y-Z) Compounds of Formula lf (compounds of Fe. Mui I where Y is CHR150, CHR15S, or CHR150-N = CR7) can be prepared by contacting halides of Formula 29 with several nucleophiles (Scheme, 21). The appropriate alcohol or thiol is treated with a base, for example sodium hydride, to form the corresponding alkoxide or thioalkoxide which acts as the nucleophile.

- - SCHEME 21 Some aryl halides of Formula 29 may be prepared by a radical halogenation of the corresponding alkyl compound (ie, H instead of the halogen in Formula 29), or by an acidic cleavage of the corresponding methyl ether (i. e, OMe instead of a halogen in Formula 29). Other aryl halides of Formula 29 can be prepared from suitable alcohols of Formula 30 by halogenation methods very well known in the art (see Carey, F.A., Sundberg, R.J.

Advanced Organic Chemistry; 3rd ed., Part B, Plenum: New York, (1990), p 122). The compounds of Formula I wherein Y is CR6 = CR6 or CHR6-CHR6 (Formula Ig and Ih, respectively) can be prepared as illustrated in Scheme 22. The treatment of the halides of Formula 29a with triphenylphosphine or a traxylphosphite yields 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 (Rd) C = 0 yields the olefin of Formula Ig.

SCHEME 22 ro- R- alkyl CJ-C4 32: 1) Halogenation 2) dehalogenation GAVE The olefins of Formula Ig can be converted to saturated compounds of Formula Ih by hydrogenation plus a metal catalyst such as palladium on carbon. This is very well known in the field (Rylander, Catalytic Hidrogenation in Organic Synthesis; Academic: New York, 1979). The alkynes of Formula Ii can be prepared by halogenation / dehalogenation of olefins of Formula Ig using known methods (March, J. Advanced Organic Chemistry; 3rd ed. , John Wiley: New York, (1985), p 924). Additionally, alkynes of Formula Ii can be prepared by known reactions of aryl halides with alkyne derivatives in the presence of a catalyst such as nickel or palladium (see J. Organomet, Chem., (1975), 93-253-257. ). The olefin of Formula Ij can also be prepared by reversing the reactivity of the reagents in Wittig or Horner-Emmons condensation. For example, the 2-alkylaryl derivatives of Formula 33 can be converted into corresponding dibromo compounds 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 can be condensed with a phosphorus-containing nucleophile of Formula 36 or 37 to proportionally the olefin of Formula Ig. Additionally, the compounds of Formula 35 can be prepared by the oxidation of the corresponding alcohols of Formula 30.

The vinyl halides of Formula Ij can be prepared by reacting phosphorus reagents of Formula 37a or 37b with carbonyl compounds of Formula 35 (Scheme 2. 3) . The preparation of the halides of Formula 37a from appropriate diethylphosphonoacetate are described by McKenna and Khawli in J. Org. Chem., (1986), 51.5467. The thiono esters of Formula 37b can be prepared from esters of Formula 37a by converting the carbonyl oxygen of the ester to thiocarbonyl (see Chem. Rev., (1984), 84, 17 and Tetrahedron Lett. , (1984), 25.2639).

SCHEME 23 l) Br2 or NBS, CH2R6 2 equiv., CO4, CR6J 'light *. 2) Morpholine With. HO, H20 A-N NBS "W-bromosuccinimide A-N R2 V - - The 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- (Cl, Br, or I) (Scheme 24). Alternatively, the O-substituted hydroxylamine can be condensed with the carbonyl compound of Formula 38 to produce oximes of Formula Ik directly. SCHEME 24 The carbamates of Formula II can be prepared by reacting the 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, the carbamates of Formula II can also be alkylated to obtain the carbamates of Formula Im.

- - Compounds of Formula I wherein Y is -CHR150-N = C (R7) -C (= N-A2-Z1) -A1-, -CHR150-N = C (R7) -C (R7) = N-A2 -A3- or -CHR150-N = C (-C (R7) = N-A2-ZX) - can be prepared by methods known in the art or by obvious modifications (see for example, WO 95/18789, WO 95 / 21153 and references to these) together with the methods described here. The compounds of Formula I wherein Y is -CHR15OC (== 0) 0-, -CHR1OC (= S) 0-, -CHR15OC (= 0) S-, CHR150C (= S) S-, -CHR15SC (= 0) N (R15) -, -CHR15SC (= S) N (R15) -, -CHR15SC (= 0) 0-, -CHR15SC (= S) 0-, -CHR15SC (-0) S-, CHR15SC (= S) S-, -CHR15SC (= NR1S) S- or -CHR15N (R15) C (= 0) N (R1S) -can be prepared by known methods or modifications obvious (see, for example US .5, 416, 110, EP 656,351 and references thereof) together with the methods described herein. The compounds of Formula In (Formula IA wherein Y is (CH2) xO, where x = 0 or 1) can be prepared by mixing them with hydroxy compounds of Formula 40 with appropriate heterocycles or activated aromatic hydrocarbons Lg-Z (where Lg is a suitable excess group, for example halogen or alkylsulfonyl) in the presence of a suitable base (for example, K2C03, KO-t-Bu or NaH) in suitable solvents (for example, acetone, dimethylformamide, dimethylsulfoxide or tetrahydrofuran) (See Scheme 26).

Where X = 0 or 1 In The compounds of Formula Lg-Z can be prepared according to the procedures found in the literature for example, Comprehensive Heterocyclic Chemistry, Pergamon Press, vol. 6, 1984, pp 463-511 or J.

Org. Chem. (1973), 38,469 or J. Het. Chem. (1979), 961 for the preparation of 1,2,4-thiadiazole, U.S. 5,166,165 or J. Chem. Soc. , Perkin Trans. 1 (1983), 967 for the preparation of 1,3,4-oxadiazole and 1,3,4-thiadiazole, -EP446.0110 or J. Med. Chem. (1992), 35.3691, for the preparation of 1, 2, 4-oxidiazole. The compounds of the present invention are prepared by combinations of reactions as illustrated in Schemes 1-26 in which Z is a radical as described in the abstract. The preparation of the compounds containing the radical Z5 [Z as described in the abstract substituted with L (defined as any group attached to Z as is marked in each of the individual Schemes)] can be carried out by a person skilled in the art. by an appropriate combination of reagents as well as a reaction second for a particular Z5-L. Such a reaction sequence can be developed in available reactions already known in the chemical area. For a general reference, see March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985) references in this regard. See the following paragraphs and Schemes as Examples of how L is defined in individual Schemes, and the preparation of the representative Examples Z5-L. Note that Z5 in Schemes 27-41 is also taken to be the radical below, such compounds linked by the methods taught in Schemes 1 to 26 can also be modified and illustrated by chemistry to give compounds I as described in the summary.

The compounds of Formula 42 in Scheme 27 can be prepared from compounds of Formula 41 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. The compounds of Formula 42 correspond to compounds of Formula 13 in Scheme 6 when Y1 = 0-N = C (R7) and in Scheme 21, reagent H0-N = CR7. SCHEME 27 0-CR-z5 =? .. HONKX7 ^ H2NOH «HO / base 41 42 The compounds of Formula 41 can be prepared from compounds of Formula 43 (Scheme 28) by Friedel-Krafts acylation with compounds of Formula; Four . (See Olah, G. "Friedel-Krafts and related reactions," Interscience, New York (1963-1964) 'for a general review). The compounds of Formula 41 can be prepared by the reaction of acyl halides, anhydrides, esters, or amides of Formula 47 with onargometalic reagents of Formula 46 (see March J. Advanced Organic Chemistry; 3rd Ed. John - - Wiley: New York, (1985), pp. 433-435 and references of this). The organometallic compounds of Formula 46 can be prepared by a reductive metallation or an exchange of a halogen-metal containing a halogen compound of Formula 45, for example, magnesium or an organolithium reagent, or by deprotonation of compounds of Formula 43 using a strong base such as lithium amide or an organolithium reagent, followed by a transmetallation. The compound 41a corresponds to the compound 14a in Scheme 8 and to the compound 41 in the Scheme 27, compound 41b corresponds to 0 = C (R6) Z in the Scheme 22 and compound 41c correspond to compound 93 (where T18 = R26) in Scheme 41. SCHEME 28 hal-CI, Br, I M'-MgX T ^ -CI CuLiZ OCOR33 CdZ OR SpR3 NR2 R33 .. R6, R7t R29 0 R26 R = alkyl C C The compounds of Formula 45 can be prepared by the reaction of the compounds of Formula 43 (Scheme 29) with, for example, bromide or chloride, with or without additional catalyst under a free radical or aromatic electrophilic halogenation conditions, depending on the nature of Z. Alternatively halogen sources, such as N-halosuccinimides, tert-butyl hypohalides or S02C12, can be used, (see March, J. Advanced Organic Chemistry; 3rd Ed. John Wiley: New York, (1985), pp. 476-479, 620-626 and references of this). For a review of halogenation of the free radical, see Huyser, 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 45 correspond to compound of Formula 15 in Scheme 7 where Lg = Br, Cl, or I and the Z-hal reagent in Scheme 24. Compounds of Formula 49 can be prepared from compounds of Formula 48 by similar procedures . The compounds of Formula 4 correspond to compounds of Formula 16 in Scheme 7 where Lg = Br, Cl or I. The compounds of Formula 36 or 37 in Scheme 23 can be prepared by the reaction of the compounds of Formula 49 with triphenylphosphine or trialkyl phosphites respectively, followed by a deprotonation with a base. See Cadogen, "Organophosphorus Reagents in Organic Synthesis," Academic Press, New York (1979) for a general treatise on these reagents. SCHEME 29 Z5-H Br. I -CHRW --- ^ hal-CHR6-Z5 R = alkyl C] -C4 36 037 is Scheme 23 Compounds of Formula 50 can be prepared from compounds of Formula 41d by treatment with percents such as perbenzoic or peracetic acid or with other peroxy compounds in the presence of an acid catalyst, followed by a resulting ester hydrolysis (Scheme 30). For a review see Plesnicar, and Trahanovsky, "Oxidation in Organic Chemistry, pt C, Academic Pres New York (1978) pp 254-267.Formula corresponds to Formula 13 in Scheme 6 when Y1 = 0 and the reagent HO-Z in Scheme 21. Compounds of Formula 45 can be prepared from compounds of Formula 50 by conversion of dialkyl thiocarbamate of Formula 52 followed by a rearrangement of Formula 53 and subsequent hydrolysis See MS Newman and HA Karnes, J. Org. Chem. (1966), 32.3980-4. Formula 54 corresponds to Formula 13 in Scheme 6 when Y1 = S and HS-Z reagent in Scheme 21.

SCHEME 30 OC (CH3> Z5,) [° 1 * • HOZ5 41 2) hydrolysis 50 HO-Z5 R "C1-C4 alkyl The compounds of Formula 55 can be converted to compounds of Formula 45, 50 or 54 via diazonium compounds, by treatment with nitrous acid followed by a subsequent reaction (Scheme 31). See some reviews such as 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 the compounds of Formula 56 with copper halides or iodide ions yields compounds of Formula 45. Treatment of the compounds of Formula 56 with copper oxide in the presence of an excess of cupric nitrate provides 50-formulations. (Cohen, Dietz, and Miser, J. Org. Chem., (1977), 42,2053). Treatment of compounds of Formula 56 with (S2) ~ 2 yields compounds of - Formula 54. Treatment of compounds of Formula 56 with S02 and Cl2 yield compounds of Formula 54a.

SCHEME 31 Z5-NH2 ^ ^ CuBr. CuCl or I * 55 56 Z5-hal hal = Br, Cl, I 45 Cu20 ^ Cu (N03) 2 HO-Z5 50 (S2T2 ».HS-Z5 54 so2 / c? 2». Z5-S02C1 54a The compounds of Formula 55 can be prepared from compounds of Formula 43 by nitration, followed by a reduction (Scheme 32) A wide variety of nitrating agents is available (see Schofield, "Aromatic.

Nitration, "Cambridge University Press, Cambridge (1980)). The reduction of nitro compounds can be carried out in a number of ways (see March, J.

Advanced Organic Chemistry; 3rd Ed. John Wiley: New York, (1985), pp 1103-4). Formula 55 corresponds to the Formula 13 in Scheme 6 when Y1 = NR15 and R15 = H. SCHEME 32 Z5-H Z ^ C ^ Z5-NH2 43 57 55 The iodides of Formula 8 can be prepared from compounds of Formula 60 by the methods described - previously in Schemes 21-26 for various Y-Z combinations. The compounds of Formula 60 in turn can be prepared from compounds of Formula 59 for interconversions of the functional group which is very well known in this field. The compounds of Formula 59 can be prepared by treatment of the compounds of Formula 58 with an organolithium reagent such as n-BuLi or LDA followed by the retention of an intermediate such as iodine (Beak, P., Snieckus, V. Acc. Chem. Res. , (1982), 15,306). Additionally, the lithium metal exchange via halogen of compound of Formula 48, where H is replaced by Br, so that an intermediate will be produced which can be retained with iodine to prepare compounds of Formula 59 (Parha, WE, Bradsher, CK Acc Chem. Res., (1982), 15, 300 (Scheme 32).

- - SCHEME 33 ion of R = C 1 -C 4 alkyl CH 2 OH, OMe, OCH 2OMe t - 1 or 2 Compounds of Formula 63 can be prepared by the reaction of compounds of Formula 61 with acylate agents of Formula 62, with or without an optional base. Suitable alkylating agents are, for example, chloroformates alkyl anhydrides, carbamoyl chlorides, or carbonylimidazoles. Alternatively, the compounds of Formula 61 can be reacted with compounds of Formula 24, (eg, phoenix, diphosgene, triphosgene, thiophosgene, N ^ N'-carbonyldiimidazole, or N, N'-thiocarbonyldiimidazole) followed by a reaction with compounds of Formula 64 with or without an optional base. Compounds of Formula 68 can be prepared by the reaction of compounds of Formula 66 with sulfonilate agents of Formula 67 (for example, methanesulfonyl chloride, trifluoromethanesulfonic anhydride) with or without an optional base. Some suitable bases include an alkali metal, alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, tertiary amines such as triethylamine and triethylene diamine, pyridine or 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU). Some suitable solvents include polar aprotic such as acetonitrile, dimethylformamide, or dimethyl sulfoxide, ethers such as tetrahydrofuran, dimethoxyethane or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons such as toluene or benzene; or halocarbons such as dichloromethane or chloroform. The reaction temperature can vary between 0 and 150 ° C the reaction time can be from 1 to 72 hours depending on the selected base, solvent, temperature and substrate.

- - SCHEME 34 Ql = 0, S. NR26? L = 0, S T9 = Cl, OCCI3, OCO (C 1 -C 4 alkyl), 1-imidazole 1,2,4-triazodil T10 = R26 > OR27, SR27, N (R26) 2 61 2) TH-H / opt.base 65 (64) x1 = o, s T1 and T2 are independently Cl, OCCI3, 0 (alkyl 1-C4), 1- imidazole, 1,2,4-triazolyl Tl 1 »OR27 , SR27, N (R26) 2 ZÍ-QÍ-u T ^ -SC ^ R27 ^ zL-Q ^ SQzR27 66 ° Pt base 68 Q2 = O, NR26 T12 = C1, R27S020 The compounds of Formula 71 can be prepared by the reaction of compounds of Formula 69 with isocyanates of Formula 70. A base such as triethylamine can be added to catalyze the reaction. The compounds of Formula 73 can be prepared by reacting the compounds of Formula 69 with silylate and germilate agents of Formula 72a or 72b, in the presence of a base such as, but not limited to, pyridine or imidazole.

Cl-S R25 ^ (72a) or ß - C SetR ^ ^ ^ ^^^ base ^ Q3 - Sio Ge Compounds of Formula 76 may be prepared by reaction of compounds of Formula 74 with alkylate agents of Formula 75 which include alkyl, haloalkyl- or sulfonates-aryl such as methanesulfonate ethyl lactate, 2-methoxyethyl trifluoromethanesulfonate or cyanomethybenzenesulfonate, and alkyl halides such as benzyl bromide and propargyl bromide (Scheme 36). These rentals can be conducted with or without additional base. Some suitable bases include alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, or tertiary amines such as triethylamine and pyridine, 1,8-diazabicyclo [5.4.0] undec Jan-7 (DBU), and triethylene diamine. Note that when Q4 = NH, two equivalents of the same compound 75 or two different compounds 75 can be reacted subsequently.

SCHEME 36 1 or 2 eq. ZL-QÍ-H '-13 (7S zL-O5- ^ opt base 74 76 Lgla-Cl, Br. I, OSO2V2 V2 »alkyl Cj-C6, haloalkyl Cj-Cg, phenyl, -MeC $ H -? L3« haloalkenyl and C ^, alkynyl Cj-Cg, haloalkynyl C3-Cg, alkoxyalkyl C2-Cg trialkylsilylaicosialkyl C5-C, alkylthioalkyl C- -C-61 C 1 -C 3 alkyl substituted with cyano, -C (-0) OR 26 or C (-0) N (R 26) 2 The compounds of Formula 78 can be prepared from compounds of Formula 77 by nucleophilic displacement with alkali metal alkoxides, alkali metal thioalkoxides (M + -T14) (Scheme 37). Similar shifts in compounds of Formula 80 in compounds M + -T15 provide compounds of Formula 81. Compounds of Formula 79 can be prepared by reaction with amine derivatives in a suitable solvent. The excess group Lg1 in compounds of Formula 77 and 80 are any group known in the art to be subjected to a displacement reaction of this type. Examples of suitable leftover groups include bromine, chlorine and the sulfonate and sulfonyl groups. Examples of some suitable inert solvents are dimethylformamide or dimethyl sulfoxide, dimethoxyethane and methanol.

SCHEME 37 z * - L * 1 ^ t14. z5- r'4 77 7g M-K or Na Lg = Cl, Br, -S02V or OSC ^ VV = alkyl C i -Cg, haloalkyl C j -Cg O 4 -CH 3 -C 6 H 4 T '"SCN, benzyloxy, phenylthio, benzylthio, pyrimidylmethoxy, pyridylthio, thienylthio, furanyloxy, furanthylthio, pyrimidylthio each optionally substituted 7-becyloxy, phenylthio, each optionally substituted The compounds of Formula 84 can be prepared from compounds of Formula 82 by reaction with nucleophiles of Formula 83 in the presence of an added base (Scheme 38). Similarly, reactions of compounds of Formula 54a with nucleophiles of Formula 85 leads to compounds of Formula 86. Some suitable bases include alkoxides, alkali metal such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, tertiary amines such as triethylamine, pyridine, or 1,8-diacybicyclo [5.4.0] undec-7-en (DBU) and triethylenediamine. The hydrochloric acids of formula 82 can be prepared from carboxylic acids of Formula 87 by a wide variety of methods (see March, J., Advanced Organic Chemistry, 3rd Edition, John Wiley: New York, (1985), pp 388-9 and references of these) . Carboxylic acids are widely available and can be synthesized by experts in the field by a wide variety of methods. The compounds of Formula 54a can be prepared, in addition to the method described in Scheme 31, by the halo-sulfonation of compounds of Formula 43 with chlorosulfonic acids. (for a review, see Gilbert, Sulfonation and Related Reactions, Interscience New York (1965) pp 62-83, 87-124). The compounds of Formula 54a can also be prepared by the oxidative chlorination of mercaptans of Formula 52 by water and chlorine. The sulphide, disulfide, and thioacetate derivatives derived from 52 (Formula 52a), among others, can be used for the same reaction effect. (for a review, see Gilbert, Sulfonation and Related Reactions, Interscience New York (1965) pp 202-21).

- SCHEME 38 H- -T16 (83) -COCÍ r _ COT 16 82 Base 84 T16 = OR 0, SR26 N ^ ß ^ z5- S02a, »-t" (i5) ZJ SQ2T 'Base 54a Z5- COOH ^ Z5- CC 1 87 82 Z H C1S ° 3"z5 - so? c? 43 54a Z5.SH Cl / Íl20 52"ZJ S02Q or 54a Z5-SQ6 52a Q6" a, < ^ ui, C1-C4, benzyl, S (alkylC? -C4), S-benzyl, SCOCH3 The compounds of Formula 90 (Scheme 39) can be prepared using methods already known in the art. (for references on how to prepare silyl- and germyl-substiutted compounds see The Organi c Compounds of Germani um, Michel Lesabre, Piere Mazerolles, and Jacques Satge, Dietmar Seyferth, Ed., John Wiley & Sons, new York; C. Eaborn and K.C. Pande, J. Chem. Soc. (1960) 3200-3203 M. Wieber and M. Schmidt, J. Organometal. Chem. (1963) 93-94; and WO94 / 08976). See Scheme 39 for the two methods. One method is the reductive metalation of the metal-halogen exchange of compounds of Formula 88 by dyeing a magnesium reagent or an organolithium, followed by a treatment with a silyl- or germyl-substituted halide of Formula 89. A second method is the deprotonation of compounds of Formula 43 using a strong base such as a lithium amide or an organolithium reagent followed by a treatment with a compound of Formula 89. SCHEME 39 l) Mgo R31Li) (Cl, BG, I; V 'l »J: 5 (OL Br. L) Z5 - Q7 88 90 D LiNÍR ^ o R lLi Z5 H 2) Cl, Br, l) Q7 (89) Z5- Q7 43 90 Q7 = S« R2 R 3R24 O GeR2 R23R24 R31 = C1-C4 alkyl or Compounds of Formula 92 can be prepared by the oxidation of the corresponding thio compounds of Formula 91 (Scheme 40) using methods already known for sulfide oxidation (see Schrenk, K. in The Chemistry of Sulpholes and Patai, S. Et al. , Eds., Wiley: New York, 1988). Using an equivalent of an oxidizing agent provides the sulfonyl radical (n = 1) two equivalents provide the sulfonyl radical (n = 2). Some oxidizing reagents include meta-chloroperoxybenzoic acid, hydrogen peroxide and Oxone® (KHSO5).

- - SCHEME 40 5 S_Q8 oxidizing agent Z5 SiOn-Q8 -S- O 92 91 Q8"haloalkyl Cj-Cg, phenyl (optionally substituted n-1 or 2) The compounds of Formula 94 can be prepared by treating compounds of Formula 93 with thionic reagents such as P2S5 or Lawesson's reagents (2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosptane-2. , 4-disulfide) as illustrated in Scheme 41 (see Bull. Soc.

Chim. Belg. , (1978), 87.229; and Tetrahedron Lett. , (1983), 24.3815). SCHEME 41 < II .o P2S5 ° H the z5-c-t18 ». z5-c-T18 93 94? l8 = R26, OR26 SR26, N (R26) Additionally, when Z is substituted with iodine or Lg2 (defined in Scheme 10), some R9 radicals can be introduced via a cross-catalyzed reaction with palladium (0) with the appropriate nucleophile containing R9, such as arylboronic acid, reagents aryl or alkyl zinc, and substituted acetylenes. It is to be recognized that some reagents and reaction conditions described above for the preparation of compounds of Formula I may not be compatible with certain functionalities present in the intermediates. Therefore, the incorporation of protection-deprotection sequences or interconversions of the functional group within the synthesis will help in obtaining the desired products. The use and selection of protective groups will apparently require knowledge in chemical synthesis (see, for example, Greene, T.W., Wuts, P.G. M. Protective Groups in Organic Synthesis, 2nd ed .; Wiley; New York, 1991). An expert in the field will recognize that, in some cases, after the introduction of a given reagent as marked in any individual Scheme, it may be necessary to perform some additional synthetic routine steps not described in detail to complete the synthesis of Formula compounds. I. It will also recognize that it may be necessary to perform a combination of the steps illustrated in the above Schemes in a different order from that implied by the particular sequence presented to prepare the compounds of Formula I. Also one skilled in the art will recognize that the compounds of Formula I and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation and reduction reactions to add substituents or modify existing substituents. Without further elaboration it is believed that an expert in the field using the preceding description could use the present invention to fully fill the scope. The following Examples are, therefore, to be analyzed as merely illustrative, and there must be no imitation in the disclosed. The percentages are by weight except for mixtures of solvent for chromatography or until otherwise indicated. The parts and percentages of the solvent mixtures for chromatography are by volume or until otherwise indicated. The 1HNMR spectra are reported in ppm of tetramethylsilane; S = singlet, d = doublet, t = triplet,, q = quartet, AB q = "AB" = quartet, m = multiplet, dd = doublet of doublets, dd = double of doublets of doublets, br = amplitude, br s = simple amplitude, br m = multiplet amplitude.

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

Step B: Preparation of 5-chloro-2-, 4-dihydro-4- (2-ethoxyphenyl) -2-methyl-3H-1, 2,4-triazol-3-one. To a stirred solution of 21 g of the title compound of Step A in 800 mL of dichloromethane under hydrogen are added 29.85 g of triphosgene. The reaction mixture is heated to reflux overnight, then cooled, and concentrated under reduced pressure. The resulting residue is dissolved in ethyl acetate, washed with distilled water, and then with an aqueous solution of saturated sodium chloride. The organic layer is dried (MgSO4), filtered and concentrated under reduced pressure. The solid is recrystallized from dichloromethane and the resulting solid is triturated with diethyl ether to provide 10 g of the title compound from step B as a metallic solid fused at 152-154 ° C. 1HMNR (CDC13) d 7.45 (t, 1H), 7.25 (d, 1H), 7.05 (m, 2H), 3.84 (s, 3H), 3.53 (s, 3H). Step C: Preparation of 5-Chloro-2-, 4-dihydro-4- (2-hydroxyphenyl) -2-methyl-3H-1, 2,4-triazol-3-one. The title compound of step B (7.7g) is dissolved in 65 mL of dichloromethane under nitrogen, cooled to -78 ° C, to then add 34 mL of a 1.0 M solution of tribromide boron in dichloromethane for more than 0.5 hours with stirring. After the addition, the cooling bath (acetone / dry ice) is kept in place for an additional 0.5 hours and then the reaction is left at room temperature. The ice is added to the reaction mixture which is diluted with diethyl ether and the product is extracted using a 1 N aqueous sodium hydroxide solution. The aqueous layer is acidified with a 6 N hydrochloric acid solution and extracted with dichloromethane and then with ethyl acetate. The organic layer is combined, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was triturated with diethyl ether to give 5.54 g of the title compound from step C as a white solid. 1HMNR (CDC13) d 8.18 (s, 1H), 7.11 (t, 2H), 6.91 (t, 1H), 6.76 (d, 1H), 3.56 (s, 3H).

Step D: Preparation of 2-, 4-dihydro-4- (2-hydroxyphenyl) -5-met-oxy-2-methyl-3H-1, 2,4-triazol-3-one To a stirred solution of 5.54 g of the title compound of step C in 50 L of methanol and 25 mL of 1,2-dimethoxyethane under nitrogen is added 18.6 mL of a 30% sodium methoxide solution in methanol.The reaction mixture is heated and for 5.5 hours is under reflux and then cooled to room temperature.

The mixture is diluted with diethyl ether and the product is extracted using an aqueous solution of 1 N sodium hydroxide. The aqueous layer is acidified with a 6 N hydrochloric acid solution and extracted with dichloromethane. The organic layer is dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue is triturated with diethyl ether to give 3.85 g of the title compound from step D as a white solid (85% purity). XHNMR (CDC13) d 8.40 (br s, 1H), 7.20 (m.2H), 7.03 (d, 1H), 6.94 (t, 1H), 4.00 (s, 3H), 3.48 (s, 3H). Step E: Preparation of 2,4-dihydro-4- [2- [(3-iodo-1,2,4-thiadiazol-5-yl) oxy] phenyl] -5-methoxy-2-methyl-3H-1 , 2,4-triazol-3-one. To a solution of the title compound of step D (3.0 g, 13.6 mmol) in acetone (27 mL) is added potassium carbonate (2.44 g) and 3-iodo-5- (methylsulfonyl) -1,2,4-thiadiazo KJ. Org. Chem (1973), 38, 469) (4.33 g). The mixture is stirred at room temperature for 36 hours before being diluted with water. The resulting mixture is extracted twice with methylene chloride and the combined extracts are dried with magnesium sulfate. The solution is concentrated to a solid which is triturated with hot methanol to give the title compound of step E (2.8 g, 48%). XHNMR (CDC13) d 7.55 (m, 2H), 7.46 (m, 2H), 3. 86 (s, 3H), 3.40 (s, 3H). Step F: Preparation of 2,4-dihydro-5-methoxy-l-methyl-4- [2- [[3- [(2-pyridinyl) ethynyl] -1,2,4-thiadiazol-5-yl] oxy ] phenyl] -3H-1, 2,4-triazol-3-one. To a solution of the title compound from step E (307 mg, 0.71 mmol) in DMF (4 L) is added copper (I) iodine (14 mg), triethylamine (0.347 mL), 2-ethynylpyridine (186 mg, 1.78 mmol) and bis (triphenylphosphine) palladium (II) chloride (25 mg). The mixture is stirred for 16 hours at room temperature before being diluted with ethyl acetate and washed twice with water. The aqueous phase is extracted with ethyl acetate and the combined organic phase is dried with magnesium sulfate. The solution is concentrated and the residue is purified by column chromatography (silica gel, ethyl ether) to give the title compound of step F, a compound of the invention. 1HNMR (CDC13) d 8.65 (d, 1H), 7.7 (, 1H), 7.65-7.5 (m, 3H), 7.5-7.4 (1X1, 2H), 7.3 (m, lH), 3.84 (s, 3H), 3.40 (s, 3H).

EXAMPLE 2 Step A: Preparation of ethyl l- (4-chlorophenyl) cyclopropanecarboximidate hydrochloride To a solution of 1- (4-chlorophenyl) -1-cyclopropanecarbonitrile (10 g, 53.3 mmol) in diethyl ether (56 L) absolute ethanol is added ( 3.4 L). The solution is cooled to 0 ° C and saturated with dry HCl gas. The reaction mixture is allowed to cool to room temperature for 11 days before being filtered under a flow of dry hydrogen to give the title compound of step A (11.60 g) as a white solid.1H NMR (Me2SO-dβ) d 7. 45 (s, 4H), 4.47 (q, 2H), 1.84 (m, 2H), 1.48 (m, 2H), 1. 30 (t, 3H). Step B: Preparation of 1- (4-chlorophenyl) cyclopropanecarboximidamine hydrochloride. To a solution of the title compound of step A (11.60 g, 44.6 mmol) in methanol (15 mL) is added ammonium (9.0 mL, a 7 N solution in methanol). This mixture is stirred for two days before being concentrated to give the title compound of step B (9.78 g). XH NMR (Me2SO-d6) d 9. 2-9.0 (br, 4H), 7.52-7.43 (m, 4H), 1.52 (m, 2H), 1.29 (m, 2H). Step C Preparation of 5-chloro-3- [1- (4-chlorophenyl) cyclopropyl] -1,2,4-thiadiazole.

- To a solution composed of the title step B (9.78 g, 42. 3 mmol) in water (100 mL) is added methylene chloride (200 mL), benzyltriethylammonium chloride (0.79 g) and perchloromethyl mercaptan (4.62 mL, 42.3 mmol) and the mixture is cooled in an ice bath. With efficient stirring, sodium hydroxide (6.77 g) in water (100 mL) is then added in the form of drops in such a way that the internal temperature does not exceed 10 ° C. After the addition, the cold bath is removed and the reaction mixture is stirred for 1.5 hours. The organic layer is then separated, dried with magnesium sulfate and concentrated. The brown / yellow pitch is extracted with boiling hexane and then filtered through a silica gel filter. The silica gel is washed with hexane and the solution is then concentrated to give a yellow solid which is recrystallized from ethanol to give 3.97 g of the title compound from step C as a white solid. XH NMR (CDC13) d 7.39-7.32 (m, 4H), 1.75 (m, 2H), 1.42 (, 2H). Step D: Preparation of 4- [2- [[3- [l- (4-chlorophenyl) cyclopropyl] -1,2-thiadiazol-5-yl] oxy] pheny] -2,4-dihydro-5-methoxy- 2-methyl-3H-l, 2,4-triazol-3-one. To a solution of the title compound of Step D in Example 1 (300 mg, 1.36 mmol) in acetone (3 mL) is added fresh potassium carbonate powder (244 mg) and the compound compound-title (368 mg, 1.36 mmol). The mixture is stirred at room temperature for two days before being diluted in water and the resulting mixture is extracted three times with methylene chloride. The combined organic layer is dried with magnesium sulfate and concentrated. The resulting residue is crystallized from ethanol to yield a title compound of D, a compound of the invention, as a white solid fused at 123-124 ° C. XH NMR (CDC13) d 7.52 (m, 2H), 7.44 (m, 2H), 7.36 (, 2H), 7.33 (m, 2H), 3.82 (s, 3H), 3.41 (s, 3H), 1.65 (m , 2H), 1.30 (m, 2H).

EXAMPLE 3 Step A: Preparation of ethyl 1,3-benzodioxol-5-carboximidate hydrochloride. To a solution of piperonylonitrile (10 g, 68.0 mmol) in diethyl ether (68 mL) and methylene chloride (30 mL) is added absolute ethanol (3.99 mL). The solution is cooled to 0 ° C and saturated with dry gas hydrochloric acid. The reaction mixture is left at room temperature for 5 days after which time it is concentrated and the residue is triturated with ethyl ether to give a title compound from step A (6.38 g) as a white solid.1H NMR (Me2SO-d6) d 7.80 (m, 2H), 7.18 (d, 1H), 6.23 (s, 2H), 4.61 (q, 2H), 1.47 (m, 3H).

- Step B: preparation of 1, 3-benzodioxol-5-carboximidamine hydrochloride. To a solution of the title compound of step A (6.38 g, 29.2 mmol) in ethanol is added ammonium (5.6 mL, a 7 N solution in ethanol). This mixture is stirred for 6 days before being concentrated to give the title compound of step B (5.60 g). XH NMR (Me2SO-d6) d 9.30 (s, 2H), 9.17 (s, 2H), 7.50-7.45 (m, 2H), 7.16 (d, 1H), 6.20 (s, 2H). Step C: Preparation of 5-chloro-3- (1,3-benzodioxol-5-yl) -1,2,4-thiadiazole. To a solution of the title compound from step B (5.60 g, 27.9 mmol) in water (68 mL) is added methylene chloride (136 mL), benzyltriethylammonium chloride (0.52 g) and perchloromethyl mercaptan (3.05 mL, 27.9 mmol) and the mixture is cooled in the ice bath. With efficient stirring, sodium hydroxide (68 mL, a 1.66.N solution) is added in the form of drops so 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 1 hour. The organic layer is then separated, dried with magnesium sulfate and concentrated. The brown / yellow pitch is extracted with boiling hexane and then filtered through a silica gel filter. The silica gel is washed with hexane and the solution is then concentrated to give a yellow solid which is recrystallized from ethanol to give a title compound from step C as a white solid. XH NMR (CDC13) d 7.84 (d, 1H), 7.70 (s, 1H), 6.90 (d, 1H), 6.06 (s, 2H). Step D: Preparation of 4- [2- [[3- (1,3-benzodioxol-5-yl) -1,4,4-thiadiazol-5-yl] oxy] pheny] -2,4-dihydro-5 -methoxy-2-methyl-3H-l, 2,4-triazol-3-one. To a solution of the title compound of Step D in Example 1 (300 mg, 1.36 mmol) in acetone (3 mL) is added fresh potassium carbonate powder (244 mg) and the title compound of Step C (327 mg, 1.36 mmol). ). The mixture is stirred at room temperature for two days before being diluted in water and the resulting mixture is extracted three times with methylene chloride. The combined organic layer is dried with magnesium sulfate and concentrated. The resulting residue is crystallized with ethanol to yield a title compound from step D, a compound of the invention, as a white solid fused at 168-169 ° C. XH NMR (CDC13) d 7.70 (d, 1H), 7.63 (m, 2H), 7.55 (m, 1H), 7.48 (m, 2H), 6.86 (d, 1H), 6.02 (s, 2H), 3.78 ( s, 3H), 3.37 (s, 3H).

EXAMPLE 4 Step A Preparation of 2- (methylthio) -5- (tricyclo) [3.3.1.13'7] dec-1-yl) -1,3,4-oxadiazole. To a solution of 1-adamantanecarboxylic acid hydrazide (2.0 g, 10.3 mmol) in ethanol (16 mL) is added potassium hydroxide (1.08 mL, a 10 N aqueous solution, 10.8 mmol) and carbon disulfide (0.682 mL) in drop shape. The mixture is diluted with ethanol (10 mL) and then it is heated to reflux overnight. Then methyl iodide (0.705 mL) is added and the mixture is cooled in an ice bath and stirred for 0.5 hours. The solution is concentrated and redissolved in methylene chloride. The solution is filtered through a silica gel filter and concentrated to give the title compound of step A (2.15 g) as a white solid. Step B Preparation of 2- (methylsulfonyl) -5- (tricyclo) [3.3.1. I3A dec-1-yl) -1, 3, 4-oxadiazole. To a solution of the title compound from step A (2.15 g, 7.62 mmol) in acetic acid (17 mL) is added a solution of potassium permanganate (60 mL, 0.3 M aqueous solution, 16.0 mmol) in droplet forms. A slight exotherm is controlled with an ice bath. A complete addition of sodium hydrosulfite (80 mL, 40% of an aqueous solution) is added and the resulting precipitate is filtered to give 1.84 g of the title compound of step B. XH NMR (CDC13) d 3.47 (s, 3H), 2.2-1.6 (br, several H). Step C: Preparation of 2,4-dihydro-5-methoxy-2-methyl-4- [2- [[5- (tricyclo [3.3.1.13,7] dec-1-yl) -l, 3,4- oxadiazol-2-yl] oxy] phenyl] -3H-1, 2,4-triazol-3-one. To a solution of the title compound of step D in the Example 1 (0.5 g, 2.26 mmol) in acetone (5 mL) is added potassium carbonate (406 mg) and the title compound of step B (383 mg). The mixture is stirred overnight, before being diluted with methylene chloride and washed with water. The aqueous phase is reextracted with methylene chloride and the combined organic phase is dried with magnesium sulfate so that the solution is then concentrated under reduced pressure. The residue is purified by column chromatography (silica gel, 80% ethyl ether in petroleum ether and ethyl ether) to give a title compound of step C, a compound of the invention. XH NMR (CDC13) d 7.8 (d, 1H), 7.5 (t, 1H), 7.42 (m, 2H), 3.86 (s, 3H), 3.44 (s, 3H), 2.1 (br s, 3H), 2.04 (br, 6H), 1.79 (br m, 6H).

EXAMPLE 5 Step A. Preparation of 3- [(2-chlorophenyl) methoxy] -5- (methylthio) -1,2,4-thiadiazole.

To a solution of 3-hydroxy-5-thiomethyl-1,2,4-thiadiazole (J. Het Chem., (1979), 961) (0.8 g) in DMF (10 mL) is added potassium carbonate. (1.12 g) bromide 2-chlorobenzyl. The mixture is stirred at room temperature for 3 days before being diluted with ethyl acetate.

The resulting mixture is washed with water and dried with magnesium sulfate. The solution is concentrated and the residue is purified by column chromatography (silica gel, then 20% then 40% then 60% after 80% ethyl ether in petroleum ether). The fractions are combined, concentrated and repurified by column chromatography (silica gel, then 5% then 10% ethyl ether in petroleum ether to give a title compound from step A. 1H NMR (CDC1) d 7.45 (m, 2H), 7.3 (m, 2H), 5.03 (s, 2H), 2.71 (s, 3H) Step B: Preparation of 4- [2- [[3- [(2-chlorophenyl) methoxy] -1, 2 , 4-thiadiazol-5-yl] oxy] phenyl] -2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one To a solution of title compound of step To (0.23 g) in acetic acid (lmL) and acetic anhydride (lmL) is added hydrogen peroxide (0.17 mL of a 30% aqueous solution) and the solution is left overnight.An extra portion of hydrogen peroxide ( 0.085 mL) is then added and then left for an additional two hours, the solution being previously diluted with ethyl ether, the resulting mixture is washed with Na 2 SO (an aqueous %), aqueous NaHC03 and then dried with magnesium sulfate. The solution is concentrated to give 0.32 g of the compound. This material was redissolved in acetone (5 mL) and potassium carbonate (0.218 g) and the title compound from Step D in Example 1 (0.232 g) was added. The mixture is stirred at room temperature for two hours before being diluted with water and extracted twice with methylene chloride. The organic extracts are dried with magnesium sulfate and concentrates. Crystallization of the residue from the ethyl ether gave the title compound of Step B (240 mg), a compound of the invention, as a solid with a melting point of 107-108 ° C. 1H NMR (CDC13) d 7.6-7.5 (m, 3H), 7.5-7.35 (m, 3H), 7.3 (m, 2H), 5.49 (s, 2H), 3.82 (s, 3H), 3.4 (s, 3H) ).

EXAMPLE 6 Step A: Preparation of dimethylpropanedinitrile. To a solution of malonitrile (10.0 g, 151.4 mmol) in DMF (300 mL) is added iodomethane (28.3 mL, 0.45 mol) and potassium carbonate (52.23 g, 379 mmol) and the reaction mixture is stirred overnight. The mixture is then diluted with ethyl ether, and washed with water and a saturated aqueous solution of NaCl, the organic layer is dried with magnesium sulfate. The concentration of a - compound title of step A (4.84 g) as an oil containing 20 mol% DMF. 2H NMR (CDC13) d 1.84 (s). Step B: Preparation of a-cyano- -methylpropanimidamide. (See Tet. Lett., 1990, 31, 1969). To a solution of trimethyl aluminum (20.6 ml, 2 M in toluene) in toluene (41 ml) at 0 ° C ammonium chloride (2.20 g) is added in small portions. With a complete addition the cooling bath is diluted and the mixture is stirred for more than two hours. To this mixture is added a title compound solution from step A (4.84 g) in toluene (20 ml) and the mixture is heated overnight. The mixture is cooled and drained to a slurry of silica gel (200g) in methylene chloride (300ml). The mixture is stirred for 5 minutes and filtered, and the filter is washed with methanol. The concentration of the filtrate produced 3.52 g of the title compound from step B. X H NMR (Me 2 SO-d 6) d 8.7-8.3 (br s, 3 H), 1.75 (s, 6 H). Step C: Preparation of 5-chloro-a, a-dimethyl-1,2,4-thiadiazole-3-acetonitrile. To a solution of the title compound from step B (3.52g, 31.4mmol), in methylene chloride (75ml) is added perchloromethyl mercaptan (3.4ml) and the mixture is cooled in an ice bath. 17.5 ml of triethylamine is added so that the internal temperature does not exceed 10 ° C.

- With a complete addition the cooling bath is removed and the mixture is stirred for 1.5 hours. The mixture is then washed with water, IN HCl and dried with magnesium sulfate. The mixture is concentrated and the residue is extracted with hot hexanes, filtered through a silica gel filter and concentrated to give the title compound of step C (1.3g). XH NMR (CDC13) d 1.84 (s). Step D: Preparation of 5- [2- (1, 5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1, 2,4-triazol-4-yl) phenoxy] -, α-dimethyl -1, 2,4-thiadiazole-3-acetonitrile. To a solution of the title compound from step D in Example 1 (0.5 g, 2.26 mmol) in acetone (5 ml) is added potassium carbonate (406 mg) and the title compound of step C (426 mg). The mixture is stirred overnight under reflux before being diluted with water. The mixture is extracted three times with methylene chloride and the organic extracts are dried with magnesium sulfate. The solution is concentrated and the residue purified by column chromatography (silica gel, ethyl ether) to give the title compound of step D (100 mg) a compound of the invention, as a brown solid. 1 H NMR (CDC13) d 7.57 (m, 2 H), 7.48 (m, 2 H), 3.83 (s, 3 H), 3.40 (s, 3 H), 1.77 (s, 6 H).

EXAMPLE 7 Step A: Preparation of 5- (methylthio) -3- (phenylmethoxy) -1,2,4-thiadiazole. To a solution of 3-hydroxy-5-thiomethyl-1,2,4-thiadiazole (J.Het. Chem., (1979), 961) (4.06 g) in DMF (50 mL) is added potassium carbonate (5.7 g) benzyl bromide (3.56 ml). The mixture is stirred at room temperature for 3 days before being diluted with ethyl ether. The resulting mixture is washed twice with water and the organic layer dried with magnesium sulfate. The solution is concentrated and the residue purified by column chromatography (silica gel, then 5% then 10% ethyl ether in petroleum ether). To give a title compound of step A (2.0 g). XH NMR (CDC13) d 7.5-7.4 (m, 2H), 7.45-7.3 (m, 3H), 5.43 (s, 2H), 2.68 (s, 3H). Step B: Preparation of 2,4-dihydro-5-methoxy-2-methyl-4- [2- [[3- (phenylmethoxy) -1,2,4-thiadiazol-5-yl] oxy] phenyl] -3H -1, 2, 4-triazol-3-one. To a solution of the title compound of step A (2.0 g) in acetic acid (20 ml) and acetic ahydride (20 ml) is added hydrogen peroxide (4.0 ml, and a 30% aqueous solution) and the solution is left room temperature. After 6 hours the solution diluted with ethyl ether and the resulting mixture are washed with Na 2 SO 3 - (10% aqueous solution), water and aqueous NaHCO 3. The organic layer is dried and concentrated with magnesium sulfate to give 1.95 g of the compound which was used without purification.

This material is dissolved in acetone (18ml) and potassium carbonate (1.3g) and the title compound of step B in the Example 1 (1.6g) where it is added. The mixture is stirred at room temperature before being diluted with ethyl acetate. The resulting mixture is washed twice with water and with a saturated aqueous solution of NaCl. The organic layer is dried with magnesium sulfate and concentrated to give a title compound from step B (2.75g), a compound of the invention. XH NMR (CDC13) d 7.6-7.3 (m, 9H), 5.37 (s, 2H), 3.79 (s, 3H), 3.40 (s, 3H).

EXAMPLE 8 Preparation of 2,4-dihydro-4- [2- [(3-hydroxy-1,2,4-thiadiazol-5-yl) oxy] phenyl] -5-methoxy-2-methyl-3H-1, 2, -triazol-3-one. To a solution of the title compound from Step B in Example 7 (2.68g, 6.52 mmol) in benzene (35ml) is added aluminum chloride (1.74g) and the mixture is stirred at room temperature overnight. Additional aluminum chloride (0.87 g) is added and the mixture is stirred for an additional 4 hours, being previously cooled with water and extracted with ethyl acetate, twice with methylene chloride and twice with methanol with 20% methylene chloride. The combined organic phases are dried with magnesium sulfate, concentrated and triturated with petroleum ether to yield a title compound of Example 8 (1.78g), a compound of the invention as an oil. H NMR (CDC13) d 7.3-7.1 (m, 4H), 3.98 (s, 1H), 3.89 (s, 3H), 3.41 (s, 3H).

EXAMPLE 9 Preparation of [5- [2- (1, 5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1, 2,4-triazol-4-yl) phenoxy] -1, 2, 4-thiadiazol-3-yl] trifluoromethanesulfonate. To a solution of the title compound of Example 8 (0.28 g, 0.87 mmol) in methylene chloride (4 ml) is added triethylamine (0.182 ml), a catalytic amount of dimethylaminopyridine and trifluoromethanesulfonic anhydride (0.176 ml) and the solution is left for the night. The mixture is then diluted with ethyl ether, washed with IN HCl and aqueous NaHCO 3. The organic layer is dried with magnesium sulfate and concentrated. The purification of the residue is by column chromatography (silica gel, 60% then 80% ethyl ether in petroleum ether) to give the title compound of Example 9, a compound of the invention, contaminated with an equal amount of the title compound from step D in - 10 - Example 1. XH NMR (CDC1) d 7. 6-7 .4 (, 4H), 3. 84 (s, 3H), 3. 41 (s, 3H).

EXAMPLE 10 Step A: Preparation of 2,2-diethoxyethanimide hydrochloride. To a solution of diethyxyacetonitrile (6.46g, 50.0 mmol), in methanol (50 ml) is added sodium methoxide (2.7 g, 50 mmol) and the mixture is stirred at room temperature for 24 hours. Ammonium chloride (5.35 g, 0.1 mol) is added and the mixture is stirred for more than 24 hours at room temperature before being concentrated to give a title compound of step A contaminated with sodium chloride (13.14 g) as a white solid. 1 H NMR (Me 2 SO-d 6) d 9.0-8.4 (br s, 4 H), 5.32 (s, 1 H), 3.62 (q, 4 H), 1.19 (t, 6 H). Step B: Preparation of 5-chloro-3- (diethoxymethyl) -1,2,4-thiadiazole. To a solution of the title compound from step A (13.14 mmol) in water (120 ml) is added methylene chloride (240 ml), benzyltriethylammonium chloride (0.5 g) and mercaptanoperchloromethyl (5.46 ml) to then cool the mixture in a bath of ice. With an efficient stirring, sodium hydroxide (120 ml, an aqueous solution at 1.66 N) is added in the form of drops so 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 0.5 hours. The organic layer is then separated, dried with magnesium sulfate and concentrated. The brown / yellow pitch is extracted with boiling hexane and the hot solution is filtered through a silica gel filter. The silica gel is washed with 5% ethyl ether in hexanes and the solution is then concentrated to give the title compound from step B. XH NMR (CDC13) d 5.68 (s, 1H), 3.8-3.65 (q, 4H ), 1.28 (t, 6H). Step C: Preparation of 4- [2- [[3- (diethoxymethyl) -1,2,4-thiadiazol-5-yl] oxy] pheny] -2,4-dihydro-5-methoxy-2-methyl-3H -1,2, 4-triazol-3-one. To a solution of the title compound of Step D in Example 1 (345 mg, 1.53 mmol) in acetone is added fresh potassium carbonate powder (378 mg) and the title compound of compound B (345 mg, 1.53 mmol). The mixture is stirred at room temperature for 16 hours before being diluted in water and the resulting mixture is extracted three times with methylene chloride. The combined organic layer is dried and concentrated with magnesium sulfate. The purification of the material is purified by column chromatography (silica gel, 80% ethyl ether in petroleum ether then ethyl ether) to give the title compound of step C, a compound of the invention. XH NMR (CDC13) d 7.6-7.4 (m, 4H), 5.53 (s, 1H), 3.81 (s, 3H), 3. 8-3.65 (, 4H), 3.40 (s, 3H), 1.23 (t, 6H).

EXAMPLE 11 Step A: Preparation of l-methoxy-3- (2-nitrophenoxy) benzene. The 3-methoxyphenol (11.52 g, 95.2 mmol) is added to a suspension of potassium carbonate (13. Ig, 95.2 mmol) in 100 ml of dry N, N-dimethylformamide at room temperature after the reaction is stirred at room temperature For 10 minutes. Then 2-fluoronitrobenzene (12.2 g, 86.5 mmol) is added. The mixture is stirred at room temperature for 16 hours. The reaction mixture is stirred with ice water and the solids were filtered. The filter is washed with water to yield 15.3 g of the title compound of step A as a solid of melting point 50 to 52 ° C. XH NMR (CDC13; 300 MHz) d 3.80 (s, 3H), 6.60 (m, 2H), 6.75 (m, 1H), 7.05 (, 1H), 7.2-7.3 (m, 2H), 7.5 (m, 1H) ), 8.0 (m, 1H). Step B: Preparation of 2- (3-methoxyphenoxy) benzenamine. A solution of l-methoxy-3- (2-nitrophenoxy) benzene (15. Og, 61.2 mmol) and 15 ml of water in 150 ml of acetic acid is heated in a steam bath at 65 ° C, at this temperature, Iron powder (11.3 g, 202 mmol) is added in drops noting the exotherm after each addition. The reaction temperature is maintained between 65-85 ° C by the addition of the flow and by a water cooling bath.

After an additional 10 minutes stirring at 85 ° C, the reaction mixture is cooled to room temperature, diluted with methylene chloride and filtered through Celite®. The filtrate is washed with water, then with saturated sodium bicarbonate, and dried with magnesium sulfate. The solvent is removed under reduced pressure to yield 12.1 g of the title compound of step B as an oil. XH NMR (CDC13; 300 MHz) d 3.8 (s, 5H total), 6.6-6.7 (m, 3H), 6.7 (m, 1H), 6.81 (dd, J = 1.5, 7.8 Hz, 1H), 6.89 (d , J = 7.9 Hz, 1H), 7.0 (m, 1H), 7.2 (m, 1H). Step Cj Preparation of 2,2-dimethyl-N- [2- (3-methoxyphenoxy) phenyl] hydrazinecarbozamide. The title compound of step D (11.8 g, 55.0 mmol) is dissolved in 120 ml of dry toluene, to this solution is added diphosgene (10.8 g, 55.0 mmol). The mixture was refluxed with washing water for 4 hours. The reaction mixture is cooled to room temperature, concentrated under reduced pressure to then dissolve oil in dry tetrahydrofuran (100 ml). To this solution is added 1,1-dimethylhydrazine (4.0 g, 66 mmol) at room temperature and the reaction is stirred sequentially at room temperature for 16 hours. The reaction mixture is concentrated under reduced pressure to obtain solids which are washed with water and dried by suction to yield 16.5 g of the title compound from step C as a solid with melting point of 93-95 ° C. 1 HOUR NMR (CDC13; 300 MHz) d 32.40 (s, 6H), 3.80 (s, 3H), 5.2 (s, 1H), 6.7-6.8 (, 2H), 6.85 (m, 1H), '7.0 (m, 2H) ), 7.1-7.3 I (m, 2H), 8.29 (d, J = 7.9 Hz, 1H), 8.6 (s, 1H). Step D: Preparation of 5-chloro-2,4-dihydro-4- [2- (3-methoxyphenoxy) phenyl] -2-methyl-3H-1, 2,4-triazol-3-one. The title compound of step C is dissolved in 600 ml of methylene chloride and cooled to 0 ° C at this temperature, triphosgene (15.9g, 53.5 mmol) is added. The reaction mixture is refluxed for 16 hours, cooled to room temperature and washed with water. The organic layer is then dried with magnesium sulfate and concentrated under reduced pressure to produce a crude oil which is purified by silica gel chromatography using 3: 2 hexanes: ethyl acetate as the eluent to yield 14.7g of the title compound. of step D as an oil. ? K NMR (CDC13; 300 MHz) d 3.47 (s, 3H), 3.77 (s, 3H), 6.61 (m, 2H), 6.70 (m, 1H), 7.01 (dd, J = 1.5, 8.2 Hz, 1H), 7.2-7.3 (m, 2H), 7.34-7.42 (m, 2H). Step E: Preparation of 5-chloro-2,4-dihydro-4- [2- (3-hydroxyphenoxy) phenyl] -2-methyl-3H-1, 2,4-triazol-3-one. The title compound of step D (12.6 g, 38.0 mmol) is dissolved in 300 ml of dry toluene and to this solution - aluminum chloride (30 g) is added., 228mmol) at room temperature with a slight exotherm at 35 ° C. The reaction mixture is subsequently refluxed for 4 hours, cooled to room temperature and carefully added ice in chunks. The crude slurry is extracted twice with diethyl ether, and the combined extracts are washed with a saturated aqueous solution of NaCl and dried with magnesium sulfate. The solvent is removed under reduced pressure to produce an oil which is subsequently purified by silica gel chromatography using 3: 2 hexanes: ethyl acetate as eluent to yield 9.50 g of the title compound of step E, a compound of the invention as a solid with a melting point of 135-138 ° C. XH NMR (CDC13; 300 MHz) d 3.46 (s, 3H), 6.46 (t, J = 2.2 Hz, 1H), 6.50-6.59 (m, 3H total), 6.99 (dd, J = 1.3, 8.3 Hz, 1H), 7.11 (t , J = 8.1 Hz, 1H), 7.20 (dd, J = 1.2, 7.6 Hz, lH) 7.32-7.40 (m, 2H).

EXAMPLE 12 Preparation of 2-, 4-dihydro-4- [2- (hydroxyphenoxy) phenyl] -5-methoxy-2-methyl-3H-1, 2,4-triazol-3-one. The title compound of step D in Example 11 (8.7 g, 27.4 mmol) is dissolved in 300 ml of methanol and then sodium methoxide (7.4 g, 137 mmol) is added at room temperature, noticing a slight exotherm. The reaction mixture is refluxed for 16 hours, cooled to room temperature and concentrated under reduced pressure to semi-solids. The semi-solids are diluted with 1 N HCl and extracted twice with diethyl ether, washed with a saturated aqueous solution of NaCl, and dried with magnesium sulfate. The solvent is removed under reduced pressure to produce crude solids which were subsequently purified by silica gel chromatography using 1: hexanes: ethyl acetate as eluent to yield 5.80 g of the title compound of Example 12, a compound of the invention, as a solid with a melting point of 153-155 ° C. ? E NMR (CDC13; 300 MHz) d 3.37 (s, 3 H), 3.87 (s, 3 H), 6.4-6.5 (m, 2 H), 6.55 (, 1 H), 6.9 (br s, 1 H), 7.0 (m , lH), 7.1-7.2 (, 2H), 7.3-7.4 (m, 2H). EXAMPLE 13 Preparation of 4- [2- [3- [(2-chlorophenyl) methoxy] phenoxy] phenyl] -5-methoxy-2-methyl-3H-1,2,4-triazol-3-l-one. The title compound of Example 12 (0.30 g, 0.95 mmol), 2-chlorobenzyl bromide (0.21 g, lmmol) and potassium carbonate (0.14 g, 1 mmol) are combined at room temperature in 10 ml of dry acetonitrile and the resulting mixture it is stirred at room temperature for 16 hours. The reaction mixture is filtered and the filtrate is concentrated under reduced pressure to obtain solids which are triturated with hexane and dried by suction to obtain 0.32 g of the title compound of the title compound.

Example 13, a compound of the invention, as a solid fused at 112-114 ° C. 1K NMR (CDC13; 300 MHz) d 3.38 (s, 3H), 3.85 (s, 3H), 5.13 (s, 2H), 6.6-6.8 (m, 3H), 7.0 (m, 1H), 7.2-7.4 (m, 7H), 7.5 (m, 1H).

EXAMPLE 14 Step A: Preparation 1- (4-Chlorophenyl) cyclopropanecarboximidamide hydrochloride. Small portions of ammonium chloride are added (3.01 g, 56.3 mmol) to a trimethylaluminium solution (56.3 mmol) in toluene (70 ml) at 0 ° C. After the addition is complete, the mixture is warmed to room temperature, stirred for 1.5 hours and then a dropwise solution of 1- (4-chlorophenyl) -1-cyclopropanecarbonitrile (10Og, 56.3 mmol) is added in drops. toluene (30ml) The reaction mixture is heated at 80 ° C for 15 hours, cooled to room temperature and stirred overnight. The reaction mixture is poured into a slurry of silica gel (250 g) and dichloromethane (300 ml).

The resulting mixture is stirred for 10 minutes and filtered, and the silica gel is washed with methanol (300 ml). The combined filtrates are concentrated to obtain 11. lg - of the title compound of step A as a white solid. 1 HOUR NMR (Me 2 SO-de) d 9.08 (m, 2H), 7.40 (m, 5H), 1.77 (m, 1H), 1. 52 (m, 2H), 1.27 (m, 1H). Step B: Preparation of 5-clo-3- [1- (4-chlorophenyl) cyclopropyl] -1,2,4-thiadiazole. The title compound from step A (11.1 g, 48.1 mmol) is dissolved in water (100 mL) and combined with a perchloromethyl mercaptan solution (8.94 g, 48. mmol) and benzyltriethylammonium chloride (0.55 g, 2.4 mmol) in dichloromethane. (200mL). The resulting biphasic mixture is stirred vigorously, and cooled to 0 ° C to then treated with a solution of sodium hydroxide (7.70 g, 193 mmol) in water (100 mL) maintaining by the addition of droplets a reaction temperature below 12 ° C. The mixture is warmed to room temperature and stirring continues for 1 hour. The layers are separated and the organic phase is washed with water, dried with MgSO 4, filtered and concentrated. The residual oil is purified by flash column chromatography on silica gel and eluted with 2% ethyl acetate / hexane to provide 2.68 g of the title compound from step B as a pale yellow solid. X H NMR (Me 2 S0-d 6) d 7.41 (m, 4 H), 1.62 (m, 2 H), 1.42 (m, 2 H). Step C: Preparation of N- (2-methoxy-6-methylphenyl) -2,2-dimethylhydrazinecarboxamide.

- To a stirred solution of benzene (108 g, 1.09 mol) in ethyl acetate (750 ml) at 0 ° C is added in the form of drops 2-methoxy-6-methylaniline (126 g, 911 mmol), dissolved in ethyl acetate (250 ml) for more than 20 minutes. The reaction mixture is slowly warmed to room temperature and then heated for reflux for 1 h. The solution is cooled to room temperature and concentrated under reduced pressure to provide the crude isocyanate as a dark reddish liquid which is redissolved in ethyl acetate (llt) and cooled to 0 ° C. 1,1-Dimethylhydrazine (55.Og, 91 lmmol) is also added in the form of drops for more than 30 min. And then the mixture is warmed to room temperature and stirred overnight. The mixture is cooled, filtered, and the solid is washed with ethyl acetate and dried to obtain 200 g of the title compound of step C as a white solid with a melting point of 151-153 ° C. 1 HOUR NMR (CDC13) d 7.58 (br s, 1H), 7.10 (t, 1H), 6.84 (d, 1H), 6.74 (d, 1H), 6.74 (d, 1H), 5.22 (br s, 1H), 3.80 (s, 3H), 2.63 (s, 6H), 2.31 (s, 3H). Step D: Preparation of 5-chloro-2,4-dihydro-4- (2-methoxy-6-methylphenyl) -2-methyl-3H-1, 2,4-triazol-3-one. The title compound from step C (100.0 g, 447.9 mmol) was suspended in ethyl acetate (ILt) and added dropwise, via mechanical pump, for 3.5 hours to a phosgene solution (111 g, 1.79 mol) in ethyl acetate (1.5Lt) which was heated to reflux. After the addition is complete, the mixture is refluxed for 3 hours, cooled to room temperature and stirred overnight. The solution is concentrated under reduced pressure and the residue is dissolved in ethyl acetate and water and extracted 4 times with ethyl acetate. The combined organic phases are washed with a saturated aqueous NaCl solution, dried with MgSO 4, filtered and concentrated to obtain 111.4 g of the title compound of step D as a pale yellow solid with a melting point between 132-134 ° C. 2H NMR (CDC13) d 7.34 (t, 1H), 6.93 (d, 1H), 6.85 (d, 1H), 3.79 (s, 3H), 3.54 (s, 3H), 2.20 (s, 3H). Step E: Preparation of 5-chloro-2,4-dihydro-4- (2-hydroxy-6-methylphenyl) -2-methyl-3H-1, 2,4-triazol-3-one. To a stirred solution of the title compound from step D (15. Og, 59.3mmol) in benzene (200mL) at 0 ° C is added aluminum chloride (23.7g, 178mmol) in small portions. The mixture is warmed and stirred at room temperature for 2 days. The mixture is poured into ice and water and then extracted four times with ethyl acetate.

The organic phases are washed with saturated aqueous NaCl solution, dried with MgSO 4, filtered and concentrated to an oil which was purified by flash column chromatography on silica gel to obtain 13.6 g of the title compound of step E as a pale orange solid with melting point of 175-178 ° C. XH NMR (CDC13) d 8.11 (s, 1H), 6.92 (t, 1H), 6.71 (d, 1H), 6.41 (d, 1H), 3.56 (s, 3H), 2.12 (s, 3H). Step F: Preparation of 2,4-dihydro-4- (2-hydroxy-6-methylphenyl) -5-methoxy-2-methyl-3H-1, 2,4-triazol-3-one. To a stirred solution of the title compound of passage E '(133.5 g, 557.0 mmol) in tetrahydrofuran (1.5 Lt) is added sodium methoxide in the form of drops (25% by weight methanol, 382 mL, 1.67 moles) the mixture heat at reflux for 3 h, cool to room temperature and then dilute with aqueous ammonium chloride and ethyl acetate. The aqueous layer is acidified (pH 4-5) with IN HCl and extracted three times with ethyl acetate. The organic phases are washed with a saturated aqueous solution of NaCl, dried with MgSO 4, filtered and concentrated to obtain a dark brown solid which is triturated with ethyl acetate to yield 75. Og of the title compound of step F as a white solid with melting point of 194-196 ° C. X H NMR (Me 2 SO-d 6) d 9.91 (s, 1 H), 7.17 (t, 1 H), 6.78 (m, 2 H), 3.84 (s, 3 H), 3.30 (s, 3 H), 2.03 (s, 3 H).

Step G: Preparation of 4- [2- [[3- [l- (4-chlorophenyl) cyclopropyl] -1,2,4-thiadiazol-5-yl] oxy] -6-methylpheni] -2,4-dihydro- 5-methoxy-2-methyl-3H-1, 2,4-triazol-3-one.

- - Potassium carbonate (1.41 g, 10.2 mmol) is added to a solution of title compound from step B (2.30 g, 8.50 mmol) and the title compound of step F (2.00 g, 8.50 mmol) in N, N-dimethylformamide. (lOOml) The mixture is stirred for 16 h at room temperature to then be diluted with water and extracted three times with ethyl acetate. The combined organic extracts are washed with a saturated aqueous solution of NaCl, dried with MgSO 4, filtered and concentrated. The residual oil is purified by flash column chromatography on silica gel and eluted with 40% ethyl acetate / hexane to obtain 2.49 g of the title compound of step G, a compound of the invention, as a pale yellow solid -121 ° C. XH NMR (CDC13) d 7.34 (m, 7H), 3.82 (s, 3H), 3.42 (s, 3H), 2.28 (s, 3H), 1.65 (m, 2H), 1.31 (, 2H).

EXAMPLE 15 Step A: Preparation of N- [2- (bromomethyl) phenyl] -2,2-dimethylhydrazinecarboxamide. A solution of o-tolyl isocyanate (50.4 g) and 75.2 g of N-bromosuccinimide in 800 L of carbon tetrachloride are heated to reflux. Benzoyl peroxide (1.1 g) is added and the mixture is heated at reflux for 1.5 h. The solution is cooled to room temperature and the precipitate is removed by filtration. The filtrate is concentrated in vacuo and redissolved in 500 mL of toluene and cooled to 5 ° C. Then 1, 1-dimethylhydrazine (30 mL) is added in 20 mL of toluene in the form of drops. The reaction mixture is stirred at room temperature overnight. The precipitated solid is collected by filtration and redissolved in 1 liter of dichloromethane. The organic solution is washed with 500 ml of water and then with 500 ml of a saturated solution of sodium chloride. The organic phase is dried (MgSO), filtered and concentrated to give 58 g (56% yield) of the title compound of step A as a beige solid. XH NMR (CDC13) d 8.6 (br s, 1H), 8.00 (d, 1H), 7.30 (m, 2H), 7.04 (t, 1H), 5.70 (br s, 1H), 4.52 (s, 2H), 2.67 (s, 6H). The material is used in the next step without further characterization. Step B: Preparation of 5-chloro-4- [2- (chloromethyl) phenyl] -2,4-dihydro-2-methyl-3H-1, 2,4-thiazol-3-one. The title compound of step A (58 g) is dissolved in 800 mL of dichloromethane and 86 g of triphosgene is added in one portion. A slight exotherm is observed and then the mixture is heated to reflux overnight. The reaction mixture is cooled and the solvent removed in vacuo. The resulting solid is dissolved in one liter of ethyl acetate and washed with 500 mL of water, 500 mL of a saturated solution of aqueous sodium bicarbonate, and 500 mL of an aqueous solution of aqueous sodium chloride.

- -The organic phase is dried (MgSO4), filtered and concentrated to give a dark oil which is solidified. The solid is triturated in 2: 1 hexane: n-butyl chloride to yield 32 g of a beige solid. Recrystallization of this solid from 150 mL of hot methanol yields 21 g of the title compound from Step B as a white fluffy solid fused at 122-124 ° C. A second batch is obtained from the recrystallization of the mother liquor. XH NMR (CDC13) d 7.45-7.6 (m, 3H), 7.25 (, 1H), 4.68 (d, 1H), 4.46 (d, 1H), 3.56 (s, 3H). Approximately 10% of 4- [2- (bromomethyl) phenyl] -5-chloro-2,4-dihydro-2-methyl-3H-2,4-triazol-3-one is observed in the NMR spectrum. Step C: Preparation of Oxima 1- (3-hydroxyphenyl) ethanone. To a solution of 6.8 g of 3'-hydroxyacetophenone in 50 mL of pyridine under a nitrogen atmosphere is added 3.5 g of hydroxylamine hydrochloride. The solution is refluxed for 5 h, and then the solvent is removed in vacuo. The residue is mixed with an aqueous solution of IN HCl and extracted twice with 50 mL of ethyl acetate. The combined organic phases are dried with MgSO 4, filtered and concentrated in vacuo to give 7.8 g of the title compound of step C, as a pale amber oil. XH NMR (CDC1) d 7.25 (d, 1H), 7.23 (s, 1H), 7.2 (m, -2H), 7.10 (d mating more satisfactory, 1H), 6.84 (ddd, 1H), 2.24 (s, 3H). Step D: Preparation of 5-chloro-2,4-dihydro-4- [2- [[[1- (3-hydroxyphenyl) ethylidene] amino] oxy] methyl] phenyl] -2-methyl-3H-1, 2,4-triazol-3-one. To a solution of the title compound of step C (3.9 g, 25.8 mmol) and the title compound of step B (6.6 g, . 8 mmol) in acetonitrile (100 mL) is added K2CO3 (7 g, 51 mmol). The mixture is refluxed for 4 h and then stirred at room temperature overnight. It is then heated (7 h) and left at room temperature (72 h), and in this way the mixture is diluted with water and extracted with ethyl acetate (3X50 mL). The combined organic phases are dried (MgSO4) and concentrated under reduced pressure and thus obtain an oil. Chromatography of this oil in silica gel (3: 2 hexanes: ethyl acetate as eluent) gives 5.47 g of the title compound of step D, a compound of the invention, as an oil. 1H NMR (CDC13) d 8.09 (br s, 1H), 7.62 (d, 1H), 7.51 (m, 2H), 7.22 (m, 4H), 6.9 (d, 1H), 5.08 (q, 2H), 3.44 (s, 3H), 2.25 (m, 4H). This material is used in Example 16 without further characterization.

- - EXAMPLE 16 Preparation of 2,4-dihydro-4- [2- [[[[1- (3-hydroxyphenyl) ethylidene] amino] oxy] methyl] phenyl] -5-methoxy-2-methyl-3H-1, 2 , 4-triazol-3-one. To a solution of the title compound of step D in the Example 15 (5.4.14.5 mmol) in tetrahydrofuran (350 mL) is added sodium methoxide as a 30% solution in methanol (6.8 mL, 36 mmol) and the resulting mixture is stirred at room temperature overnight. The mixture is diluted with IN HCl in diethyl ether (20 mL) and concentrated under reduced pressure to obtain a semi-solid. The residue is mixed with ethyl acetate and the insoluble portion is removed by filtration. The organic phase is concentrated under reduced pressure to obtain 4.36 g of the title compound of Example 16, a compound of the invention as an oil. 1H NMR (CDC13) d 7.6 (dd, 1H), 7.45 (m, 2H), 7.25 (m, 3H), 7.19 (m, 2H), 6.85 (dd, 1H), 5.08 (AB q, 2H), 3.92 (s, 2H), 3.39 (s, 3H), 2.24 (s, 3H). This material is used in Example 17 without further characterization.

EXAMPLE 17 Preparation of 1,1-dimethylethyl [3- [1- [[[2- (1, 5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1, 2,4-triazole-4] -yl) phenyl] methoxy} imino] ethyl] phenoxy] acetate.

- - To a solution of the compound title of example 16 (260 mg, 0.7 mmol) in tetrahydrofuran (20 mL) is added sodium hydride as a 60% dispersion oil (35 mg) followed by t-butyl bromoacetate (0.10 mL, 0.7 mmol). The mixture is stirred at room temperature for two hours and then diluted with water and extracted with 3 portions (20 mL) of ethyl acetate. The combined organic phases are dried with (MgSO4) and concentrated under reeduced pressure to obtain 290 mg of the title compound of Example 17, a compound of the invention, as an oil. 1 H NMR (CDC13) d 7.6 (m, 1 H), 7.45 (m, 2 H), 7.23 (m, 4 H), 6.87 (, 2 H), 3.91 (AB q, 2 H), 4.63 (s, 2 H), 3.91 (, s, 3H), 3.39 (s, 3H), 2.28 (s, 3H), 1.48 (s, 9H).

EXAMPLE 18 Step A Preparation of methyl (2-bromomethyl) benzeneacetate. Methyl o-tolylacetate (24 g), N-bromosuccinimide (27.2 g) and benzoyl peroxide (about 50 mg) are mixed in 200 mL of carbon tetrachloride and heated to reflux with a high intensity light source for 1.5 h. After cooling the precipitate is removed by filtration and the filtrate is concentrated in vacuo to yield 36 g (about 100% yield) of the title compound of step A as an amber oil. ? H NMR (CDC13) d 7.34 (m, 1H), 7.26 (m, 2H), 7. 16 (m, 1H), 4.57 (s, 2H), 3.80 (s, 2H), 3.69 (s, 3H). ** Step Bj Preparation of methyl 2- ^ [[(benzoylamino) oxy] methyl] benzeneacetate. The benzohydrohexamic acid (17 g) and the potassium carbonate (18.7 g) are suspended in 200 L of acetonitrile and the mixture is stirred at 60 ° C for 30 minutes.

A solution of 28 g of the title compound of step A in 100 mL of acetonitrile It is added in the form of drops for 0.5 h. The mixture is stirred at 60 ° C for 3 h and then cooled to room temperature overnight. The filtrate is concentrated in vacuo. It is reheated for 4 more hours. The mixture is cooled and filtered. The filtrate is concentrated in vacuo. The residue is mixed in 200 mL of ethyl acetate and washed with 100 mL of an aqueous solution of 6% potassium carbonate. The washed aqueous part is extracted with 100 mL of ethyl acetate. The combined organic phases are washed with 100 mL of water. The organic phase is dried (MgSO4)filter and concentrate in vacuo to yield 31.5 g (93% yield) of the title compound of step B as an orange oil. . XH NMR (CDC13) d 9.09 (br s, 1H), 7.60 (m, 2H), 7.47 (m, 1H), 7.37 (m, 3H), 7.29 (m, 3H), 5.14 (s, 2H), 3.88 (s, 2H), 3.71 (s, 3H).

- Step C: Preparation of hydrochloride methyl 2- [(aminooxy) ethyl] benzene acetate. To a solution of HCl in methanol (prepared by adding 20 mL acetyl chloride slowly in 200 mL of methanol) is added the title compound of step B (31.5 g). The mixture is heated at 60 ° C for 1.5 h. The solvent is removed in vacuo. The residue is taken up in 100 mL of diethyl ether and stirred at room temperature by minutes. The ether is decanted and the solid is taken up in 100 mL of tetrahydrofuran and heated to approximately 50 ° C. The mixture is cooled in an ice water bath and the solids are collected by filtration to produce 11. 5 g (47% yield) of the title compound from step C as a white solid melted at 169-170 ° C. Step Dj Preparation of methyl 2- [[[[1- (4-hydroxyphenyl) ethylidene] amino] oxymethyl] benzeneacetate. The 4 '-Hydroxyacetophenone (81.7 mg) and the title compound of step C (1.39 g) is dissolved in 40 L of pyridine. The solution is heated at 90 ° C overnight and cooled to room temperature. The pyridine is removed in vacuo and the residue taken in 40 mL of pyridine.

The solution is heated at 90 ° C overnight and cooled to room temperature. The pyridine is removed in vacuo and the residue is taken up in 40 mL of an IN HCl solution and extracted with a solution of ethyl acetate - (3X 50 mL). The combined organic layer is dried (MgSO4), filtered and concentrated in vacuo to yield 1.96 g of the title compound of step D as an amber oil. 1 HOUR NMR (CDC13) d 7.51 (d, 2H), 7.45 (m, 1H), 7.28 (m, 3H), 6.78 (d, 2H), 5.25 (s, 2H), 3.82 (s, 2H), 3.68 (s) , 3H), 2. 19 (s, 3H). Approximately 20% of the Z isomer is also observed. This material is used in subsequent steps without further purification. Step E: Preparation of dimethyl [2- [[[[1- (4-hydroxyphenyl) ethylidene] amino] oxy] methyl] phenyl] propanedioat or. The title compound from step D (1.87 g, 6 mmol) is dissolved in 10 mL of dimethyl carbonate. A mixture of 480 mg of sodium hydride (60% oil dispersion) is added in 10 mL of tetrahydrofuran and the mixture is heated to reflux for 1 h. The mixture is cooled to room temperature overnight, is quenched with 15 mL of an IN HCl solution and extracted with ethyl acetate (3 x 25 mL). The combined organic layers are dried with filtered (MgSO.sub.4) and concentrated in vacuo to yield 2.33 g of crude product, the title compound of step E, as an amber oil. XH NMR (CDC13) d 7.5 (m, 3H), 7.4 (m, 3H), 6.79 (d, 2H), 5.25 (s, 2H), 5.10 (s, 1H), 3.68 (s, 6H), 2.18 ( s, 3H). This material is used in subsequent steps without further purification. Step F: Preparation of dimethyl [2 - [[[[1- (4-hydroxyphenyl) ethylidene] amino] oxy] methyl] phenyl] -5-methoxy-2-methyl-3 (2H) -isoxazolone. The N-methylhydroxylamine hydrochloride (1.5 g) is dissolved in 25 mL of methanol. A solution of 2.0 g of potassium hydroxide dissolved in 25 mL of methanol is added and cooled with an ice bath. After 15 min, the precipitated potassium chloride is removed by filtration. A solution of 2.2 g of the title compound from step E in 10 mL of methanol is added to the filtrate. The resulting mixture is stirred at room temperature overnight. The mixture is diluted with water, acidified with HCl and extracted with methylene chloride (3 x 30 mL). The combined organic phases are dried (MgSO 4), filtered and concentrated in vacuo to obtain 1.95 g of an amber oil which is dissolved in 30 mL of toluene and 3 mL of methanol. A 10% solution of trimethylsilyldiazomethane in hexane (3 mL) is added dropwise and the solution is stirred at room temperature for 2 h. The solvents are removed in vacuo and the residue is purified by flash chromatography (1: 1 hexane: ethyl acetate as eluent). The third elution component is collected to yield 200 mg of the title compound of step F, a compound of the invention, as an amber oil. XH NMR (CDC13) d 7.52 (d, -1H), 7.42 (m, 2H), 7.32 (m, 3H), 6.72 (m, 3H), 5.24 (AB q, 2H), 3.94 (s, 3H), 3.44 (s, 3H), 2.16 (s, 3H). A smaller amount of the Z isomer is also observed.

EXAMPLE 19 Preparation of [3- [2- (1, 5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol-4-yl) phenoxy] phenyl] trifluoromethanesulfonate. To a solution of the title compound of Example 12 (313 mg, 1 mmol) in dichloromethane (10 mL) is added trifluoromethanesulfonate anhydride (0.17 mL, 1 mmol) and pyridine (0.08 mL, 1 mmol). The mixture is stirred at room temperature overnight, diluted with water, acidified with IN HCl and extracted with three 20 mL portions of dichloromethane. The combined organic phases are dried with (MgSO4), filtered and concentrated in vacuo in order to produce an oil that is purified by flash chromatography (1: 1 hexane: ethyl acetate as eluent) The component of the first elution is collected to obtain 100 mg of the title compound of Example 19, a compound of the invention, as an amber oil. XH NMR (CDC13) d 7.42 (m, 3H), 7.3 (m, 1H), 7.04 (m, 3H), 6.96 (t, 1H), 3.83 (s, 3H), 3.38 (s, 3H).

EXAMPLE 20 Step A: Preparation of 2- (3-bromomethyl) -2-methyl-l, 3-, dioxolane. The compound 1- (4-bromomethyl) ethanone (60.6 g, 0.3 mol), ethylene glycol (83.7 mL, 1.5 mol), and p-toluenesulfonic acid (0.15 g) is dissolved in benzene (250 mL) and heated to reflux All night long using a Dean-Stark device. Water and some ethylene glycol has been separated and cooled (at room temperature) the mixture is poured into water (300 mL) and the resulting mixture is extracted with 1-chlorobutane (2xl00mL). The combined organic phases are dried with (MgSO4) and concentrated to have the crude product as a yellow oil. The oil is purified by vacuum distillation (64-74 ° C / 19 Pa (0.14 'mm Hg)) to have 70.1 g of the title compound of step A as a low color oil (96% yield). Step B: Preparation of 1- [3- [tris (trifluoromethyl) germyl] phenyl] ethanone. A 250 mL flask neck-4 is loaded with a suspension of magnesium pieces (0.61 g, 0.025 mol) in 5 mL of THF. A solution of the title compound from step A is dissolved in 35 mL of THF and added with drops; A few iodine crystals to the mixture then a small portion of the solution is added. A reflux heating is required to start the reaction; the reaction is refluxed for 2 hours followed by the completion of the addition of the title compound from step A. After cooling the mixture to 63 ° C, a solution of tris (trifluoromethyl) germanium iodide (3.9 mL, 0.02 mol) is added. ) dissolved in THF (20 L) in small aliquots, allowing the exotherm in each addition to maintain the temperature between 62-69 ° C. The mixture is refluxed an additional 3 hours, and then dried at room temperature overnight. The mixture is poured into a solution of saturated ammonium chloride (100 mL). The following is to remove the organic layers and extraction with diethyl ether, the combined phases are dried with (MgSO.sub.2) and concentrated to have 8.9 g of a dark-colored oil. This oil is dissolved in acetone (400 mL) so that IN HCl (3 mL) is added. The resulting mixture is refluxed overnight. The mixture is concentrated, followed by a second addition of acetone (300 mL) and IN HCl (2 mL), and then reflux for 6 hours. The mixture is concentrated, and the residue is dissolved in diethyl ether and washed with saturated NaHCO 3. The organic layers are dried with (MgSO4) and concentrated. The dark brown oil is purified by filtration finishing 1.5 inches from the column of silica gel, eluted with 15% ethyl acetate / hexane to have 2.9 g (37% of both steps) of the title compound of step B as a low oil color. 2H NMR (CDC13) d 8.284 (s, 1H), 7.9-8.0 (m, 2H), 7.2 (t, 1H), 2.586 (s, 3H). Step C Preparation of maximum 1- [3- [tris (trifluoromethyl] germyl] phenyl] ethanone Sodium acetate trihydrate (1.22 g, 9 mmol) is added to a solution of hydroxylamine hydrochloride (0.62 g, 9 mmol) in water (7 mL), and this solution is added to a solution of the title compound of step B (2.95 g.7.4 mmol) in methanol (20 mL). The mixture was refluxed overnight and concentrated in vacuo. The mixture is treated with water and then extracted with methylene chloride (3x120 mL). The combined organic layers are dried with (MgSO4) and concentrated to obtain 2.74 g of a brown oil. This oil was chromatographed and eluted with 15 ° ethyl acetate / hexane to yield 1.72 g (56% yield) of the title compound of step C as a low color oil. This oil was crystallized to have a solid fused at 69-72 ° C. Step D: Preparation of 2,4-dihydro-5-methoxy-2-methyl-4- [2 - [[[[1- [3- [tris (trifluoromethyl) germyl] phenyl] ethylidene] amino] oxijmeth]] phenyl ] -3H-1, 2,4-thiazol-3-one.

- - A neck flask 4 of 125, sodium hydride (0.18 g, 4.5 mmol, 60% dispersion of mineral oil) was suspended in 8 mL of THF. The title compound of step C (2.0 g, 6.9 mmol) is dissolved in dry THF (5 mL) and added with droplets causing evolution of the gas. The mixture was then cooled to room temperature for 20 min, and then a solution of the title compound from step B in Example 15 (0.39 g, 1.5 mmol) was dissolved in Dry THF (5 L) is added in the form of drops. The thickener is added dry THF (3 L). The mixture is heated to reflux overnight, and then cooled to room temperature. Additional sodium hydrate (0.18 g, 4.5 mmol) is added and the reflux is restored for 6 hours. The mixture is cooled, and then stirred at room temperature overnight. Sodium hydrate (0.06 g, 1.5 mmol) is added followed by dry methanol (0.5 mL, 1.5 mmol) which was added cautiously slowly causing evolution of the gas. The mixture is refluxed for 3 hours and then allowed to cool to room temperature. Few drops of 2-propanol are added, the mixture is concentrated to only a small amount of remaining liquid. Hexane (100 L) is added, and the mixture is filtered and passed through 1 inch silica gel column eluted with a 1: 1 mixture of methylene chloride / ethyl acetate (500 mL) to have 0.72 g of a yellow oil - -after concentrate. This crude oil is purified by medium pressure with liquid chromatography (MPLC) using 20% ethyl acetate / hexane to yield the title compound of step D, a compound of the invention as an oil (0.27 g, 28%). XH NMR (CDC1 d 7.941 (s, 1H), 7.7 (d, 1H), 7.55 (m, 2H), 7.4-7.5 (m, 2H), 7.1 (t, 2H), 5.2- 5.4 (q, 2H), 3.889 (s, 3H), 3.413 (s, 3H) ), 2.152 (s, 3H).

EXAMPLE 21 Step A Preparation of 1- [3- [dimethyl (3,3,3-trifluoropropyl) silyl] phenyl] ethanone. A 250 L 4-neck flask is loaded with a suspension of magnesium pieces (1.09 g, 0.041 mol) in 8 L of THF. A solution of the title compound from step A in Example 20 was dissolved in THF (20 mL) and added slowly; A few iodine crystals are added to the mixture after a small portion of the solution has been added. A reflux heating is required to start the reaction; the reaction is refluxed for 3 hours followed by the completion of the addition of the title compound from step A. After cooling the mixture to 48 ° C, a solution of 3,3,3-trifluoropropyldimethylchlorosilane (7.82 g, 0.041 mol) is added. ) dissolved in THF (8 L) in small aliquots, allowing the exotherm in each addition to maintain - the temperature between 48-64 ° C. The mixture is refluxed an additional 5 hours, the mixture is poured into a saturated ammonium chloride solution (200 mL). The following is to remove the organic layers and extraction with diethyl ether, the combined phases are dried with (MgSO4) and concentrated to have 12.27 g of a yellow oil.

This oil is then dissolved in acetone (500 mL) to be added IN HCl (6 mL) The resulting mixture is refluxed overnight.The concentration, followed by the separation between water and diethyl ether, is dried with (MgSO4) of the organic phase to yield 10-79 g (94% total of both steps) the title compound of step A as a yellow oil. XH NMR (CDClj) 6 8.078 (s, 1H), 7.9 (d, 1H), 7.7 (d, 1H), 7.484 (t, 1H), 2.625 (s, 3H), 1.9-2.1 (m, 2H), 1.0 (m.2H), 0.359 (s, 6H). Step B: Preparation of oxim 1- [3- [dimethyl (3,3,3-trifluoropropyl) silyl] phenyl] ethanone. Sodium acetate trihydrate (7.76 g, 0.057 mmol) is added to a solution of hydroxylamine hydrochloride (3.96 g, 0.057 mmol) in water (59 mL), and to this solution is added to a solution of the title compound of step A (10.7 g, 0.039 mmol) in methanol (78 mL). The mixture is then refluxed overnight and concentrated in vacuo. The mixture is treated with water and then extracted with methylene chloride (3x120 mL). The combined organic layers are dried (MgSO4) and concentrated to obtain 11.34 g of a yellow oil. This oil is chromatographed and eluted with 10% ethyl acetate / hexane to yield 9.41 g (83% yield) of the title compound from Step B as a low color oil.

This oil is put to crystallize to have a solid fused at 69-72 ° C. Step C: Preparation of 4- [2- [[[[1- [dimethyl- (3,3,3-trifluoropropyl] silyl] phenyl] ethylidene] amino] oxymethyl] phen] -2,4-dihydro -5-methoxy-2-methyl-3H-1,2,4-thiazol-3-one A flask neck 4 of 250, sodium hydride (0.84 g, 0.021 mmol, 60% dispersion of mineral oil) The suspension is suspended in 50 L dry THF The title compound of step B (2.0 g, 6.9 mmol) is dissolved in dry THF (15 mL) and added with droplets causing evolution of the gas.The mixture is then stirred at room temperature by 1 h, and then a solution of the title compound from Step B in Example 15 (1.78 g, 6.9 mmol) is dissolved in dry THF (15 mL) is added as droplets.The mixture is heated at 35 ° C overnight , and then methanol (2.2 mL, 55 mmol) is added cautiously slowly causing evolution of the gas.The mixture is refluxed overnight.Some drops of 2-propanol are added, the mixture is concentrated to only a small amount of remaining liquid It is added of Hexane (100 mL), and the mixture is filtered and passed through 1 inch silica gel column eluted with a 1: 1 methylene chloride / ethyl acetate mixture (1500 mL) to have 3.35 g of an orange oil. This crude oil is purified with (MPLC) using 1.2% methanol / methylene chloride to yield the title compound of step C (1.31 g, 37%), a compound of the invention as an oil. XH NMR (CDC13) d 7.7 (s, 1H), 7.6 (m, 2H), 7.4-7.5 (m, 3H), 7.4 (t, 1H), 7.2 (d, 2H), 5.2-5.3 (q, 2H) ), 3.882 (s, 3H), 3.401 (s, 3H), 2.201 (s, 3H), 2.0 (, 2H), 1.0 (m, 2H), 0.32 (s, 5.5H).

For the methods described herein at the same time with methods known in the art, the following compounds of Tables 1 to 7 can be prepared. The following abbreviations are used in the Tables as follows: tertiary, n = normal, i = iso, c = cycle, Me = methyl, Et = ethyl, Pr = propyl, i-Pr = isopropyl, Bu = butyl, Hex = hexyl, F = phenyl, Ome = methoxy, Oet = ethoxy, Sme = methylthio, CN = cyano, SCN = thiocyanate, N02 = nitro, TMS = trimethylsilyl, Bzl = benzyl, ada = 1-adamatil, TMG = trimethylgermyl, and THP = 2-tetrahydropyranil.

R3"H, s s £ E? B" 3-CH2OCH3 3-OCH2OCH2TMS 4-SCH2CH = CH2 3-S (0) CF2CF3 3-C * C-OCH3 4-SCN 3-CßC-TMS 3- (l-Ph-2,2-Di-Cl-c-Pr) 3-C-C-I S-GeCMe ^ CFj S-OS Me ^ Ph 3- (2-Me-4-Ph-c-Hex) 3-ada 3-Si (e) 2CF3 2-OH 3-C? C-OTHP 3-CH2S-n-Pt 3-Ge (CF3) 3 2-N (Me) Bzl 3-OCH2CF-CF 3-SOCEt 3-SCH2 ^ C.I 3-SCH2OMe 3-SCH2SEt -OGe (Me) Ph 3- (C (= 0) (3-Me-Bz¡)) 4-C (= S) Me 4- < (4-F-BzI) -OC (-0)) -C (= S) 0Et 4-C (= S) SCHF2 2-C (= 0) N (Me) 2 2-C (= S) N ( Eth -CH2CN 3-0C (-0) Me 3-0C (-S) e 4-SC (0) Me -NHC (= 0) Me 4-NHC (= S) Ph 4-0C (= 0) 0- c-Hex 4-0C (= 0) Sn-Pr -SC (= 0) OCH2CF3 2-SC (= 0) SMe 4-S (0) 20CH2CF3 4-S (0) 2N (Me) 2 - (NHS02 ( 4-Me-Ph)) 4- (OCH (4-TMS-Ph)) 2-CH20CH2 (2.4-Di-F-Ph) 4-. {(4-TMS-Ph) -C «C) - ( S- (4-TMG-Ph)) 4-5 (0) ^ 11 3- (SCH 2 (3- e-Ph)) 3- (4-pyridinyl-CH 2) -. { 4- pyridinyl -CsC) 3- (2-pyridinyl -S) 4- (2-thienyl-CH 2) 4- (2-tienU -S) - (2-furaniI-0) 4- (3-furanyl-S) 2- (4-pyrimidinyl-CH2) 2- (2-pyrimidinyl -S) -0O = CCH3 4-OCH2CH2OMe 3-OCH2S and 3-S (0) 2CH2CH2CF3 -SFO) 2CF3 2-NH2 4-C (= S) OEt 2-C (= NHK> Me -SCI = SW-Pr 2-0C (= 0) N (Me) Ph 3-OS (0) 2CH3 3 - ((4-CN-Ph) -OCH- > ) -I2- furanyl-CH-)) 3- (2-thiazoyl-CH-)) 3 - ((3-CF3-4- pyridinyl-OCH2) RJ = 3- e. V E E? -CH2OCH3 3-OCH2OCH2T S4-SCH2CH = CH2 3-SfO) CF2CF3 -Cs -OCH3 4-SCN 3-CaC-T S 3- (l-Ph-2.2-Dl-CI-c-Pr) -C = CI 3-Ge (e) CF3 3-OS? (Me) 2Ph 3- (2-Me-4-Ph-c-Hex) -ada 3-Si (Me) 2CF3 2-OH 3-CsC-OTHP -CH2S - «- Pr 3-Ge (CF3) 3 2-N (Me) Bzl 3-OCH2CF = CF2 -SCsCEt 3-SCH2CsC-l 3-SCH2OMe 3-SCH2SEt -OGe (Me) Ph 3- (C (= 0) (3-Me-BzD) 4-C (= S) Me 4 - ((4-F-BzI) -OC (= 0)) -C (= S) 0The 4-C (-S) SCHF2 2-C (= 0) N (e) 2 2-C (= S) N (Et) 2 -CH CN 3-OC (= 0) e 3-0C (= S) Me 4-SC (= 0) Me -NHC (= 0) Me 4-NHC (= S) Ph 4-OC { 0) 0-c-Hex 4-0C (= 0) Sw-Pr -SC («O) 0CH CF3 2-SC (= 0 ) SMe 4-S (0) 2OCH2CF3 4-S (0) 2N (Me) 2 - (HS02 (4-Me-Ph)) 4- (OCH2 (4-TMS-Ph)) 2-CH2OCH2 (2.4-Di) -F-Ph) 4 - ((4-T S-Ph) -C «C) - (S- (4-TMG-P)) 4-S (0) 2Ph 3- (SCH2 (3-Me-Ph )) 3- (4-pyridinyl-CH) - (4-pyridinyl -CsC) 3- (2-pyridinyl -S) 4- (2-thienyl-CH 2) 4- (2-thienyl -S) - (2- furanyl -O) 4- (3-furanyl-S) 2- (4-pyrimidinyl-CH) 2- (2-pyrimidinyl -S) -OCsCCH3 4-OCH2CH2OMe 3-OCH2SMe 3-S (0) 2CH2CH2CF3 -S (0 ) 2CF3 2-NH2 4-C (= S) 0Et 2-C (= NH) OMe -SC (= S) - / '- Pr 2-0C (= 0) N (Me) Ph 3-OS (0) 2CH3 3 - ((4-CN-Ph> OCH- >) - (2-furanyl-CH2) 3- (2-thiazoyl-CH2) 3 - ((3-CF3-4. pyridinyl -OCH2) R3-6-Me. and E £ The E2 E! -CH2OCH3 3-OCH2OCH2TMS 4-SCH2CH = CH2 3-S (0) CF2CF3 3-C = C-OCH3 4-SCN 3-C »C-TMS 3- (1-Ph-2,2-Di-Cl- -Pr) -CaC-I 3-Ge (Me) 2CF3 3-OSi ( Me) 2Ph 3- (2- e-4-Ph-c-Hex) 3-ada 3-Si (Me) 2CF3 2-0H 3-C «C-OTHP 3-CH2S - * - Pr 3-Ge (CF3) 3 2-N (Me) Bzl 3-OCH2CF = CF2 3-SC = CEt 3-SCH2CsC-l 3-SCH2OMe 3-SCH2SEt 3-OGe (Mf) 2Ph 3- (C (= 0) (3-Me-Bzl)) 4-C (= S) Me 4- ( (4-F-Bzl) -OC «») -C (= S) OEt 4-C (= S) SCHF2 2-C (= 0) N (Me) 2 2-Cf = S) N (Et) 2 -CH2CN 3-OC (= 0) e 3-OC (= S Me 4-SC (0) Me 4-NHC (= 0) Me 4-NHC (= S) Ph 4-OC (= 0) 0-c -Hex 4-0C (O) Sn-Pr 3-SC (= 0) OCH2CF3 2-SC (= 0) S e 4-S (ObOCH2CF3 4-S (0) 2N (e) 2 - (NHS02 (4-Me-Ph)) 4- (OCH2 (4 -TMS-P)) 2-CH2OCH2 (2.4-D? -F-Ph) 4 - ((4-TMS-Ph) -C = C) 3- (S- (4-TMG-Ph »4-S (0) 2Ph 3- {CH2 (3-Me-Ph)) 3 - (4-pyridinyl-CH) - (4-pyridinyl -CsC) 3- (2- pyridinyl -S) 4- {2- thienyl-CH2) 4- (2-thienyl -S) 4- (2-furanU-0) 4- (3-fu? AnU-S) 2- (4-pyrimidinyl-CH2) 2- (2-pyrimidinyl -S) 4-OC CCH3 4-OCH2CH2OMe 3-OCH2SMe 3-S (0) 2CH2CH2CF3 3-S (0) 2CF3 2-NH2 4-C (= S) OEt 2-Cf = NH) OMe 4-SC (= S) -I-PG 2-OC (= 0) N (Me Ph 3-OS (0)? CH 3 3- "4-CN-Ph) -OCH-,) 3- (2-furanyl-CH) 3- (2-thiazoU-CH2 3 - ((3-CF3-4-pyridinyl-OCH) R3 = 6-TMO. E2 E! AND? 3-CH2OCH3 3-OCH OCH2TMS 4-SCH2CH-CH2 3-S (0) CF CF3 3-CsC-OCH3 4-SCN 3-CaC-TMS 3- (l-Ph-2.2-Di-Cl-c-Pr) 3-C * C-l S-GeíMe ^ CFs 3-OSi (Me) 2Ph 3- (2-Me-4-Ph-c-Hex) 3-ada 3-S¡ (Mc) 2CF3 2-OH 3-C ^ C-OTHP 3-CH2S - «- Pr 3-Ge (CF3) 3 2-N (Me) Bzl 3-OCH2CF = CF2 3-SC * CEt 3-SCH CaC-I 3-SCH2OMe 3-SCH2SEt S-OGeMeMe ^ Ph 3- (C (= 0X3-Me-Bzl)) 4-C (= S) Me 4 - ((4-F-Bzi) -0C (O)) 4-C (= S) OEt 4-C (= S) SCHF2 2-C (= 0) N (Me) 2 2-C (= S) N (Et) 2 4-CH2CN 3-OC (= 0) Me 3-0C (= S) Me 4-SC (-0) Me 4-NHC (= 0) Me 4-NHC (= S) Ph 4-OC (= 0) 0-c-Hex 4-OC (= 0) S-n-Pt 3-SC (= 0) OCH2CF3 2-SC (= 0) SMe 4-S (0) 2OCH2CF3 4-S (0) 2N (Me) 2 4- (NHS02 (4-Me-Ph)) 4- < OCH2 (4-TMS-Ph)) 2-CH2OCH2 (2.4-D-F-Ph) 4 - ((4-TMS-Ph) -C "C) 3- (S- (4-TMG-Ph)) 4-5 (0) ^ 11 3- (SCH2 (3-Me-P)) 3-. { 4-pyridinyl-CH 2) '- (4-pyridinyl -CQ 3- (2-pyridinyl -S) 4- (2-thienyl-CH) 4- (2-thieni S) - (2-furanyl-0) 4 - (3-furanyl-S) 2- (4-pyrimidinyl-CH2) 2- (2-pyrimidinyl -S) -OC * CCH3 4-OCH2CH2OMe 3-OCH2SMc 3-S (0) 2CH CH2CF3 -S (0) 2CF3 2-NH2 4-C (= S) 0Et 2-C (= NH) OMe -SC (= S) -; - Pr 2-0C (= O) N (Me) Ph 3-OS (0) 2CH3 3- ((4-CN-Ph) -OCH- >) - (2-furanyl-CH-7) 3- (2-thiazoyl-CH-i) 3 - ((3-CF3-4-pjridinyl-CH2) -CH OCH3 -CsC-OCH3) -Cs -I -ada -CH2S -? - PG -SO-CEt -OGei e) 2Ph -C (= S) 0Et -CH2CN -NHC (= 0) Me -SC (-0 ) OCH2CF3 - (HS0 (4-Me-Ph)) - (S- (4-TMG-Ph)) - (4-pyridinyl-C = C) - (2-furanyl-0) -0CsCCH3 -S (0) 2CF3 -SC (- = S) - -Pr - (2-furanyl-CH2) Table 2 D = CH. R3 = 7-Cl. R4 = H. and E! AND! £ 2 E £ -CH2OCH3 3-OCH2OCH2TMS 4 -CH2CH-CH2 3-S (0) CF CF3 -OC-OCH3 4-SCN 3-C = C-TMS 3- (1-Ph-2,2-D? - Cl-c-Pr) 3-CaC-t 3-Ge (Me) 2CF 3 3-OSi (Me) 2Ph 3- (2-e-4-Ph-c-Hex) -ada 3-Si (e) CF 3 -OH 3-C »C -OTHP -CH2S - «- Pr 3-Ge (CF3) 2-N (Me) BzI 3-OCH2CF = CF2 -SCeCEt 3-SCH2C * CI 3-SCH2O e 3-SCH2SEt -OGe (Me) 2Ph 3- (C (= 0) f3-Me-Bzl)) 4-C (= S) Me 4 - ((4-F-Bz!) - OC (= 0) > -C (= S) OEt 4-C (= S) SCHF2 2-C (= 0) N (Me) 2 2-C (= S) N (Et) 2 -CH2CN 3-OC (= 0) Me 3-OC (= S) Me 4-SC (< = 0) Me -NHC (= 0) Me 4-NHQ = S) Ph 4-OC (= 0) 0-c-Hex 4-0C (O) Sw-Pr -SC (= 0) OCH2CF3 2-SC (= 0) SMe 4-S (0) 2OCH2CF3 4-S (0) 2N (e) 2 -. { NHS02 (4-Me-Ph)) 4- (OCH2 (4-TMS-Ph)) 2-CH2OCH2 (2.4-Di-FP) 4 - ((4-TMS-PhVCEC) - (S- (4-TMG- Ph)) 4-S (0) 2Ph 3- (SCH 2 (3- e-Ph)) 3- (4-pyridinyl-CH 2) - (4-pyridinyl -CsC) 3- (2-pyridinyl-S) 4- (2-thienyl-CH 2) 4- (2-thienyl -S) - (2-furanyl-0) 4- (3-furanyl-S) 2- (4-pyrimidinyl -CH-> 2- (2- pyrimidinyl -S) -OC • CCH3 4-OCH2CH2OMe 3-OCH2S e 3-S (0) 2CF3 2-NH2 4-C (-S) OEt 2-C (-NH) OMe -SC (= S > / - Pr 2-OC (0) N (Me) Ph S-OSiO ^ CHs 3 - ((4-CN-Ph) -OCH 2) - (2-furanU-CH) 3- (2-thiazoyl-CH 2) 3- ( (3-CF3-4- pyridinyl -OCH2) D - N. R3 * 7-I. R4 = 5- Cl,? B! E £ B E £ -CH20CH3 3-OCH2OCH2T S 4 -CH2CH = CH2 3-S (0) CF2CF3 3-C = C-OCH3 4-SCN 3-C * C-TMS 3- (l-Ph-2.2-Di-CI-c-Pt) 3-CaC-I 3-Ge (Me) 2CF3 3-OSi (Me) 2Ph 3- (2-Me-4-Ph- £ Hex) 3-ada 3-Si (Me) 2CF 3 2-OH 3-C-C-OTHP -CH 2 S -n-Ft 3-Ge (CF 3) 3 2-N (Me) Bzl 3-OCH 2 CF = CF? -SG-CEt 3-SCH2C * CI 3-SCH? 0 and 3-SCH2SEt -OGe (e) 2Ph 3- (C (= 0) (3- e-Bzl)) 4-C (= S) Me 4- ((4-F-Bzl) -OC (= 0)) -C (= S) 0Et 4-C (= S) SCHF? 2-C («0) N (Me)? 2-C (= S) N (Et) 2 -CH 2 CN 3-0C (= 0) Me 3-0C (= S) Me 4-SC (= 0) Me-HC (- = 0) Me 4-NHC ( = S) Ph 4-0C (= O) 0-e-Hex 4-OC (= 0) Sn-Pr -SC (= 0) OCH2CF3 2-SC (= 0) SMe 4-S (0) 20CH2CF3 4- 5 (0) ^ (1 ^) - (NHS02 (4-Me-Ph)) 4- (0CH2 (4-TMS-Ph)) 2-CH20CH2 (2,4-Di-F-Ph) 4 - (( 4-TMS-Ph) -GC) - (S- (4-TMG-Ph)) 4-S (0) 2Ph 3- (SCH2 (3-Me-Ph)) 3- <4-pyridin -CH 2) - (4-pyridinyl -CsC) 3- (2-pyridinyl -S) 4- < 2- thienyl -CH?) 4- (2-thienyl -S) - (2 furanyl -0) 4- (3-furanU-S) 2- (4-pyrimidinyl-CH?) 2- (2-pyrimidin-S) ) -OCsCCH3 4-OCH? CH OMe 3-0CH? SMe 3-SiO)? CH2CH? CF3 -S (0) 2CF3 2-NH? 4-C (= S) 0Et 2-C (= NH) OMe -SC (-S) - / - Pr 2-0C (= 0) N (Me) Ph 3-0S (0) 2CH 3 3-. { (4-CN-Ph) -OCH2) - (2-furanyl-CH?) 3- (2-thiazoyl-CH?) 3 - ((3-CF3-4-pyridin-OCH?) D = N. R3 = 6-I. R4 = H V E2 E £ E? -CH? OCH3 3-OCH? OCH? T S 4 -CH? CH = CH? 3-S (0) CF? CF3 -CsC-OCH3 4-SCN 3-CaC-TMS 3- (1-Ph-2.2-Di-C! -c-Pr) -CCl 3-Ge (Me)? CF 3 3 -OSi (Me)? Ph 3- (2-Me-4-Ph-c-Hex) -ada 3-Si (Me)? CF3 2-OH 3-CsC-OTHP -CH2S - «- Pr 3-Ge ( CF3) 3 2-N (e) Bzl 3-OCH CF = CF? -SCOEt 3-SCH? C * CI 3-SCH? 0Me 3-SCH? SEt -OGeíMe ^ Ph 3- (C (-0) (3-Me-Bzl)) 4-C (= * S) c 4- ((4-F-Bzl) -OC (-0)) -C (= S) OEt 4-C (= S) SCHF2 2-C (= 0) N (e> 2-C (= S) N (Et) 2 -CH2CN 3-0C (O) Me 3-OC (= S) e 4-SC (0) Me -NHC (= 0) Me 4-NHC (-S) Ph 4-0C (= 0 ) 0-c-Hex 4-0C (O) Sn-Pt -SC (= 0) 0CH2CF3 2-SC (= 0) SMe 4-S (0) OCH? CF3 4-S (0) N (Me) 2 - (NHS02 (4-Me-Ph)) 4- (OCH2 (4-TMS-Ph)) 2-CH? OCH (2,4-D¡-F-Ph) 4- (4-TMS-Ph? C ) - (S- (4-TMG-Ph)) 4-5 (0) ^ 11 3- (SCH2 (3-Me-Ph)) 3- (4-pyridine-CH?) - (4-pyridinyl -C) * C) 3- (2-pyridinyl -S) 4- (2-thienyl-CH 2) 4- (2-thienyl-S) -. {2-furanyl-0) 4- (3-furanyl-S) 2 - (4-pyrimidinyl-CH 2) 2- (2-pyrimidin-S) -OCa-CCH 3 4-OCH 2 CH 2 OMe 3-OCH 2 SMe 3-S < 0) 2CH2CH? CF3 -S (0) 2CF3 2-NH2 4-C (= S) OE? 2-C (= NH) OMe -SC (= S? -Pr 2-0C (= 0) N (Me) Ph 3-OS (0) 2CH3 3 - ((4-C -Ph > OCH2) - ( 2-furanyl-CH2) 3- (2-thiazoyl-CH2) 3 - ((3-CF3-4-pyridinyl-OCH?) Table 3 RJ = H. and E E? Bl Bl -CH? OCH3 3-OCH? OCH? TMS 4-SCH? CH = CH? 3-S (0) CF? CF3 -CsC-OCH3 4-SC 3-CsC-TMS 3- (I -Ph-2.2-Di-Cl- »Pr) -C" Cl 3 -Ge (Me)? CF3 3 -0Yes (Me)? Ph 3- (2-Me-4-Ph-¡. -Hcx) -ada 3-Si (Me) CF3 2-OH 3-CsC-OTHP -CH? S - «- Pr 3- Ge (CF3) 3 2-NfMe) Bzl 3-OCH2CF-CF2 -SCeCEt 3-SCH? O -I 3 -CH? OMe 3-SCH? SEt -OGe (Me)? Ph 3- (Cf = 0) (3 -Me-BzD) 4-C (= S) Me 4 - ((4-F-Bzl) -OC (= 0)) -C (-S) OEt 4-C (= S) SCHF? 2-C (= 0) N (Me)? 2-C (= S) N (Et)? -CH2CN 3-0C (= 0) Me 3-OC (= S) Me 4-SC (-0) Me -NHC (= 0) Me 4-NHC (-S) Ph 4-OC (= 0) 0- c-Hex 4-0C (= 0) S - «- Pr -SC (= O) OCH2CF3 2-SC (= 0) SMe 4-S (0) 2OCH? CF3 4-S < 0)? N (Me)? -fNHSO? (4-Me-Ph)) 4- (OCH? (4-TMS-Ph)) 2-CH? OCH? (2,4-D? -F-Ph) 4- "4-TMS-Ph ) -0-C) - (S- (4-TMG-Ph)) 4-S (0)? P 3- (SCH? (3-Me-Ph)) 3-. { 4- püidinü -CH?) - (4-pyridin-C) 3- (2-pyridin-S) 4- (2-thienyl-CH?) 4. { 2- thienyl -S) - (2- furanU-O) 4- (3-furanyl-S) 2- (4-pyrimidinU-CH?) 2 - (2-pyrimidin-S) -OCaCCH3 4-OCH2CH2OMe 3-OCH ? SMe 3-S (0) 2CH2CH2CF3 -S (0) 2CF3 2-NH 4-C (= S) OEt 2-C (= NH) OMe -SC (-S) - -Pr 2-OC (-0) N (Me) Ph 3-OS (0) 3CH 3 3 - ((4-CN-Ph) -OCH 2) - (2-furanU-CH?) 3- (2-thiazole -CH?) 3 - ((3- CF3-4- piridinU -OCH?) R - 6-C "CS¡ (Meh.? E £ Si E? -CH2OCH3 3-OCH? OCH? TMS 4 -CH2CH = CH2 3-S (0) CF2CF3 -C * C-OCH3 4-SCN 3- CC-TMS 3- (l-Ph-2,2-Di-Cl-c-Pr) -C * CI 3-Ge (e) 2CF3 3-OSi (Me) 2Ph 3- (2-Me-4-Ph -e-Hex) -ada 3-Si (Me)? CF3 2-OH 3-OC-OTHP -CH? S - «- Pr" 3-G? (CF3) 3 2-N (Me) Bzl 3-OCH2CF «CF -SC * CEt 3-SCH? C = CI 3-SCH? OMe 3-SCH? SEt -OGe (Me) 2Ph 3- (C (= 0) (3-Me-Bzl)) 4-C (= S) Me 4 - ((4-F-Bzi) -0C (-0)) -C (= S) OEt 4-C (= S) SCHF? 2-C (= 0) N (Meh 2-C ( = S) N (Et) 2 -CH? CN 3-0C (= O) Me 3-OC (-S) Me 4-SC (0) Me -NHC (= 0) Me 4-NHC (= S) Ph 4-0C (= O) Oc-Hex 4-OC (= 0) Sn-Pr 3-SC (= 0) OCH CF3 2-SC (= 0) SMe 4-S (0) 2OCH? CF3 4-S (0) 2N (Me) 2 - (HSO? (4-Me-Ph)) 4 - (OCH? (4-TMS-Ph)) 2-CH? OCH? (2,4-Di-F-Ph) 4 - ((4-TMS-Ph) -CeC) - (S- (4-T) G-Ph)) 4-S (0) Ph 3- < SCH (3-Me-Ph)) 3 - (4-iridinU-CH?) - (4-pyridi'-U-C & C) 3- (2-pyridin-S) 4- (2-thienyl-CH2 ) 4- (2- tienU -S) - (2-furanyl-0) 4- (3-furanU-S) 2- (4-pyrimidinU-CH?) 2- (2-pyrimidin-S) -0CsCCH3 4- OCH2CH? OMe 3-0CH? SMe 3-S (0) 2CH2CH? CF3 -S (0)? CF3 2-NH? 4-C (= S) OEt 2-C (= NH) OMe -SC (= S) - -Pr i 2-0C (= 0) N (e) Ph 3-OS (0)? CH3 3. < (4-CN-Ph) -OCH?) - (2-furanU-CH?) J 3- (2-thiazoyl-CH?) 3 - ((3-CF3-4-pyridinU-OCH?) ) Table 4 E E! AND? Bl -CH? OCH3 3-0CH? OCH? T S 4 -CH2CH = CH? 5-S 0?; F? CF3 -CsC-OCH3 4-SCN 3-CsC-T S 3- (l -Ph-2.2-D-Cl-c-Pr) -CsC-I 3-Ge (e) 2CF3 3-0Si (Me)? Ph 3- (2-Mc-4-Ph-c-Hex) -ada 3-SiMe)? CF3 2-OH 3-C = C-OTHP -CH? S - /? - Pr 3-Ge (CF 3) 3 2-N (Me) Bzl 3-OCH? CF = CF 2 -SCsCEt 3-SCH? CsC-l 3-SCH? OMe 3-SCH? SEt -OGe (e)? Ph 3- (C (= 0) I3-Me-BzD) 4-C (= S) Me 4 - ((4-F-BzlVOC (= 0)) -C (= S) OEt 4-C (= S) SCHF? 2-C (= 0) N (Me)? 2-C (-S) N (Et) 2 -CH? CK 3-0C (= 0) Me 3-OC (= S) Me 4-SC (= 0 ) Me -NHO-0) Me i 4- HC (= S) Ph 4-OC (= 0) 0-c-Hex 4-0C (= 0) S - «- Pr -SC (= 0) OCH? CF3 2-SC (= 0) SMe 4-S (0)? OCH? CF3 4-S (0)? N (Me) 2 -fNHSO? (4-Me-Ph)) 4- (OCH? (4-TMS) -Ph)) 2-CH? OCH? (2.4-D? -F-Ph) 4- "4-TMS-Ph) -C = C) - (S- (4-TMG-Ph)) 4-S ( 0)? Ph 3- (SCH? (3- e-Ph)) 3- (4- phidinU-CH?) - (4-pyridinyl-CmC) 3- (2-pyridinyl -S) 4-. { 2- tienU -CH) 4-. { 2- thienyl -S) - (2-furanyl-0) 4- (3-furanyl-S) 2- (4-pyrimidinyl-CH 2) 2- (2-pyrimidinyl -S) -OCsCCH 3 4-OCH 2 CH α OMe 3- OCH2SMe 3-S (0) 2CH CH2CF3 -S (0) 2CF3 2-NH? 4-C (= S) OEt 2-C (= NH) OMe -SC (= S) - / - Pr 2-0C (= O) N (Me) Ph 3-0S (O)? CH3 3 - (( 4-CN-Ph) -OCH2) -i2-furanU-CH?) 3- (2-thiazoyl-CH?) 3 - ((3-CF3-4-pyridinyl-OCH?) Table 5 D3 «CH. D2 - CH. D1 - = CH. R3"H. v RÜ BiL RÜ J¿1 4-Cl 2,4-Di-Cl 4-C * C-I 4-O-C-O-T? P 3-F 2-Me 3-CH2OEt 3-CH OBzl 2-1 3-CF3 4-CH2SMe 3-O -? - FT 4-CH-CH2 3-C "CH 3-CeC-OMe 4-OCH2CF3 4-S (0) 2CF3 2-CN 2-N02 4-SCN 4-SF5 3-TMS 3-TMG 3-CsC-TMS 3-0-Ge (/ - Pt) 3 4-C (-0) Me 4-C (= S) Me 3-C (O) 0Bzl 4-C (= 0) N (Me) 2 4-C (= S) N (Me) 2 3-0C (* O) Ph 3-OC (-S) Ph 4-NHC (= 0) CH 3 4 -NHC (= S) Me 3-OC (= OK> -f-Bu 3-0C (O) N (Me) 2 2-OS (0) 2CF3 4-N (Me) S (0) 2CH3 2-Ph 2- (2-CN-Ph) 3 - ((3-CF3-Ph) -CH20) S-SiO ^ Ph 3-C ^ C-Ph 4- (4-pyridine-C «C) 4-OCH2CH-CH2 4-SEt 3-C (= 0) SMe 2- (2-C -Bzl) 4-OCH2CF = CF2 4-OH 3-SC (sO) -n-pentyl 3-SCHF2 3-OCH2OCH2-T S 3-0-S1 (/ - Pr) 3 3-S (0) 2? CH2CF3 3-S (0) CH3 3-S (0) CHF2 3-S (0) 2CH3 3-N (Me) 2 3-C (-S) SMe 3-SC (-S) Bzl 2-S (0) 2N (Me) 2 3 - ((2-F-Ph> 0) 3-CH 2 CH "C (Cl) 2 D3 = N. D2 «N. D] - C H. R3 = 3-Me. \ Sil Eli RÜ Eü 4-Cl 2,4-D¡-Cl 4-C-C-I 4-C * C-0-THP 3-F 2-Me 3-CH OEt 3-CH2OBzI 2-1 3-CF3 4-CH2SMe 3-Ow-Pr 4-CH; H2 3-CßCH 3-CC-OMe 4-OCH2CF3 -S (0) 2CF3 2-C 2 -N? 2 4-SCN .SF5 3 -TMS 3-TMG 3-C * C-TMS -0-Ge (1-Ft) 3 4-C (-0) Me 4-C ("S) Me 3-C (-OK> Bzl 4-C (-S) N (Me) 2 3-0C ("O) Ph 3-OC (-S) Ph 4 -NHC (0) CH 3 4- HC (= S) Me 3-0C (O) -0-f -Bu 3-0C (O) N (Me) 2 2-OS (0) 2CF3 4-N (Me) S (0) 2CH3 2-Ph 2- (2-C -Ph) 3 - ((3-CF3-Ph> CH20) 3-S (0) 2Ph 3-CsC-Ph 4- (4-pyridinU -CSC) 4-OCH CH-CH2 4-SEt 3-C (-0) SMe 2- (2-CN-Bzl) 4-OCH2CF-CF2 4-OH 3-SC ("0) -n-pentyl 3-SCHF2 3-OCH2OCH2-TMS 3-0-Si (/ - Pr) 3 3-S (0) 2? CH2CF3 3-S (0) CH3 3-S (0) CHF2 3-SiO) 2CH3 3-NfMe ^ 3-C (-S) SMe 3-SC (= »S) Bzl 2-S (0) 2N (Me) 2 3 - ((2-F-Ph) -0) 3-CH 2 CH-C (Cl) 2 Table 6 D3 = CH. D ^ CH. D1 »CH. R3 - H. Y E Ei 1 E EÜ 4-Cl 2,4-Di-CI 4-CsC-I 4-CßC-O-THP 3-F 2-Me 3-CH2OEt 3-CH2OBzl 2-1 3-CF3 4-CH2SMe 3-O -? - Pt 4 -CH "CH2 3-C" CH 3-CßC-OMe 4-OCH2CF3 4-S (0) CF3 2-CN 2-N02 4-SCN -SF5 3-TMS 3-TMG 3-CßC-TMS 3-O-Ge0-Pr) 3 4-C (0) Me 4-C (-S) Me 3-C (0) OBzl -C ()) N (Me) 4-C ("* S) N ( Me) 2 3-0C (= 0) Ph 3-OC (-S) Ph -NHC (-0) CH 3 4 -NHC ("S) Me 3-OC (0) -0-y-Bu 3-OC ( -0) N (Me) 2 -OS (0) 2CF 3 4-N (Me) S (0) 2CH 3 2- Ph 2-. { 2-CN-Ph) - ((3-CF3-Ph) -CH20) 3-S (0) 2Ph 3-CC-Ph 4- (4-pyridine -CC) -OCH CH-CH 2 4-SEt 3-C (> 0) SMe 2-. { 2-CN-Bzl) -OCH2CF-CF2 4-OH 3-SC (= 0) -? - pentiI 3 -CHF -OCH2OCH2-TMS 3-0-Si (1-Pr) 3 3-S (0) 20CH2CF3 3 -S (0) CH3 -S (0) CHF2 3-S (0) 2CH3 3-1 ^ (1 ^ 3-C (-S) SMe -SC (= S) Bzl 2-S (0) 2N (Me ) 2 3 - ((2-F-Ph) -0) 3-CH2CH-C (CI) 2 D3 - N. D2 «N. D '» CH.R3 - 3- e.V E sü Eü RÜ 4- Cl 2,4-Di-Cl 4-C "Cl 4-CaC-O-THP 3-F 2-Me 3-CH 2 OEt 3-CH 2 O Bzl 2-1 3-CF 3 4-CH 2 SMe 3-O -? - PG 4-CH = CH2 3-C "CH 3 -G-C-OMe 4-OCH 2 CF 3 4-S (0) 2 CF 3 2-CN 2 -N0 2 4-SCN 4-SF 5 3-TMS 3-TMG 3-CsC-TMS 3-0-Ge (/ - Pr) 3 4-C (-0) Mc 4-C (-S) Me 3-C (-0) OBzl 4-C (= 0) N (Me) 2 4-C (-S) N (Me) 2 3-OC (= 0) Ph 3-0C (-S) Pb 4 -NHC (-0) CH 3 4 -NHC (-S) Me 3-OC («0) -0 - / - Bu 3-0C (-0) N (Me) 2 2-0S (0) 2CF3 4-N (Me) S < 0) 2CH3 2-Ph 2- (2-CN-Ph) 3 - ((3-CF3-Ph) -CH 0) S-SiO ^ Ph 3-CaC-Ph 4- (4-pyridinyl -C »C) 4-OCH2CH-CH? 4-SEt 3-C (-0) SMe 2- (2-CN-Bzl) 4-OCH 2 CF = CF 2 4-OH 3-SC (= 0) -fl-pentiI 3-SCHF? 3-OCH2OCH2-TMS 3-0-Si (/ - Pr) 3 3-S (0) 20CH? CF3 3-S (0) CH3 3-S (0) CHF? 3-S (0) 2CH3 3-N (Me> 3-C (= S) SMe 3-SC («S) Bzl 2-S (0) 2N (Me) 2 3 - ((2-F) -Ph> 0) 3-CH2CH = C (Cl) 2 Table 7 2-C (= 0) N (Me) 2 2-C (= S) N (Et)? 3-OC (= S) Me 4-SC (= 0) Me 4-OC (= 0) 0-c-Hex 4-OC (= 0) S - »- Pr 4-S (0) 2OCH? CF3 4 -S (0) 2N (Me) 2)) 2-CH2OCH? (2,4-Di-F-Ph) 4 - ((4-TMS-Ph) -C »C) 3- (SCH (3-Me) -Ph)) 3- (4-pyridin-CH?) 4-. { 2- thienyl-CH?) 4- (2-thienyl -S) 2- (4-pyrimidinyl-CH?) 2- (2-pyrimidin-S) 3-OCH? SMe 3-S (0)? CH2CH? CF3 4-C (= S) OEt 2-C (= NH) OMe • OS (0) 2CH3 3 - ((4-CN-Ph) -0CH?) 3 - ((3-CF3-4- pyridinyl-OCH? ) R2 - Et. R3 = 5-NO ?, R4 - H. R10 = H. Y = CH E £ Bl Bl E! 3-CH? OCH3 3-OCH? OCH? TMS 4-SCH? CH = CH2 3-S (0) CF? CF3 3-CeC-OCH3 4-SCN 3-CsC-TMS 3- (I-Ph-2.2- Di-CI-¿-Pr) 3-CsC-l 3-Ge (Me)? CF3 3-0Si (Me) 2Ph 3- (2-Me-4-Ph-c-Hex) 3-ada 3-Si (Me) 2CF3 2-OH 3-CMC-0THP 3-CH? S -? - Pr 3 -Ge (CF3) 3 2-N (Me) Bzl 3-OCH? CF = CF2 3-SCeCEt 3-SCH? C * CI 3-SCH? OMe 3-SCH? SEt S-OGeMeMe ^ Ph 3- (C (= 0) (3-Me-Bzl).}. 4-C (= S) Me 4 - ((4-F-Bzl) -? A = 0)) 4-C (= S) OEt 4-C (= S) SCHF? 2-C (= 0) N (Me) 2 2-C (= S) N (Et)? 4-CH? CN 3-0C (-O) Me 3-0C (= S) e 4-SC (= 0) Me 4-NHC (= 0) Me 4-NHCf = S) Ph 4-OC (= 0 ) 0-c-Hex 4-OC (= 0) Sn-Pr 3-SC (= 0) OCH? CF3 2-SGf = 0) SMe 4-S (O)? OCH? CF3 4-S (0)? N (Meh 4- (NHSO? (4-Me-Ph)) 4- (0CH? Í4-TMS-Ph)): -CH? OCH? R2.4-D? -F-Ph) 4 - ((4-TMS-Ph) -C = C) 3- (S- (4-TMG-Ph)) 4-S (0)? Ph 3- (SCH? (3-Me-Ph)) 3- (4-pyridinyl-CH?) 3- (4-pyridin-C = C) 3- (2-pyridinyl-S) 4-f2-thienyl-CH?) 4- (2-tienU -S) 4- (2-furanU-0) 4- ( 3-furanyl-S) 2- (4-pyrimidinyl-CH?) 2- (2-pi ?? midin? -S) 4-OCsCCH3 4-OCH2CH? OMe 3-0CH? SMe 3-S (0)? CH? CH? CF3 3-S (0)? CF3 2-NH? 4-C (-S) 0E! 2-C (= NH) OMe 4-SC (= S) - / - Pr 2 -OC (= 0) N (Me) Ph 3-0S (0)? CH 3 3 - ((4-CN-Ph) - OCH?) 3- (2-furanU-CH?) 3- (2-thiazoyl-CH?) 3-y (3-CF-! - pyridinyl-OCH?) R2 = Me. R3 = H. R4 = H. R 1 0 = H. Y ^ CHfCH fi £ The Bl S2 3-CH? OCH3 3-OCH? OCH? TMS 4-SCH? CH = CH? 3-SfO) CF? CF3 3-CSC-OCH3 4-SCN 3-CeC-TMS 3- (l-P -2.2-D¡-CI-c-Pr) 3-CeC-l 3-Ge (Me) 2CF3 3-OSi (Me)? Ph 3- (2-Me-4-Ph-c-Hex) 3-ada 3-Si (Me) 2CF 3 2-OH 3-CaC-OTHP 3-CH 2 S-n-Pr 3-Ge (CF 3) 3 2-N (Me) Bzl 3-OCH 2 CF = CF? 3-SCßCEt 3-SCH? CBC-I 3-SCH? OMe 3-SCH? SEt S-OGcfMe ^ Ph 3- (C (-0) (3-Me-Bzi)) 4-C (= S) Me 4 - ((4-F-Bzl) -0C («O)) 4-C (= S) OEt 4-C (= S) SCHF2 2-C ("0) N (Me)? 2-C (= S) N (Et) 2 4-CH 2 CN 3-OC (= 0) Me 3-OC (= S) Me 4-SC (0) Me 4-NHC (= 0) Me 4-NHC ( = S) Ph 4-OC (= 0) 0-c-Hex 4-OC (-0) S - «- Pr 3-SC (= 0) OCH2CF3 2-SC (= 0) SMe 4-S (0) 2? CH2CF3 4-S (0) 2N (Me) 2 4- (NHS02 (4-Me-Ph)) 4- (OCH? (4-TMS-Ph)) 2-CH2OCH (2.4-Di-F-Ph) 4 - ((4-TMS-Ph) -Ca- C) 3- (S- (4-TMG-Ph)) 4-S (0)? Ph 3- (SCH? (3-Me-Ph)) 3- (4-pyriduyl-CH?) - (4-pyridinU- C «C) 3- (2-pyridinyl-S) 4- (2-tienU-CH?) 4- (2-tienU -S) - (2-furanU-O) 4- (3-furanü-S) 2 - (4-pyrimidinyl-CH2) 2- (2-pyrimidinyl -S) -OCsCCH3 4-OCH? CH? OMe 3-0CH? SMe 3-S (0) 2CH2CH? CF3 -S (0) 2CF3 2-NH? 4-C (-S) 0Et 2-C (= NH) OMe -SC (= S> / -Pr 2-OC (= 0) N (Me) Ph 3-OS (0)? CH3 3 - (( 4-CN-Ph) -OCH?) - (2-furanU-CH?) 3- (2-thiazoU-CH?) 3 - ((3-CF3-4-pyridin-OCH?) R2 = Me. R3 = 3-Me, R4 = 6-Me, R 10 = H. Y = -O-.v Bl E? Bl Bl -CH? OCH3 3-OCH? OCH? TMS 4-SCH? CH = CH? 3-S ( 0) CF2CF3 -CsC-OCH3 4-SCN 3-CsC-TMS 3- (1-Ph-2.2-D-Cl-oPr) -CsC-I 3-Ge (Me)? CF3 3-OSi (Me) Ph 3- (2-Me-4-Ph-c-Hex) -ada 3-Si (Me)? CF 3 2-OH 3-CsC-OTHP -CH? S - «- Pr 3 -GefCF3) 3 2- N (Me) Bzl 3-OCH? CF = CF; -SCsCEt 3-SCH? C = CI 3-SCH? OMe 3-SCH? SEt -OGe (Me)? Ph 3- (C (= 0) 3-Me -BzD) 4-Cf = S) Me 4 - ((4-F-Bzl) -OC (= 0) > -C (= S) OEt 4-C (= S) SCHF? 2-Cf = 0) N (Me)? 2-C (= S) N (Et) 2 -CH2CN 3-OC (= 0) Me 3-0C (= S) Me 4-SC (= 0) Me -NHC (= OÍMe 4-NHC (= S) P 4-OC (0) 0-c-Hex 4-OC (= 0) S- »7-Pr -SC (= 0) OCH? CF3 2-SC (= 0) SMe 4-S (0) 20CH? CF3 4-S (0)? N (Me) 2 - (NHSO? (4-Me-Ph)) 4- (OCH? (4-TMS-Ph)) 2-CH? OCH? (2.4-Di-F) -Ph) 4 - ((4-TMS-Ph) -CeC) - (S- (4-TMG-Ph »4-S (0) 2Ph 3- (SCH? (3-Me-Ph)) 3- ( 4-pyridinyl-CH?) - (4-pyridin-CsC) 3- (2-pyridyl) -S) 4- (2-thienyl-CH?) 4- (2-thienyl-S) -f2-furanyl-0 ) 4- (3-furanyl-S) 2- (4-pyrimidinyl-CH?) 2- (2-pyrimidinyl -S) -OCsCCH3 4-OCH? CH? OMe 3-0CH? SMe 3-S (0)? CH? CH? CF3 -S (0) 2CF3 2-NH2 4-C (= S) OEt 2-C (= NH) OMe -SC (= S) - (- Pr 2 -OC (= 0) N (Me ) Ph 3-OS (0) 2CH3 3 - ((4-CN-Ph) -OCH?) - (2-furanU-CH2) 3- (2-thiazoU-CH?) 3 - ((3-CF3-4) - pyridinyl-OCH?) R2 Me. R3 = 6-Me. R4 = H. R10 = 2-Mc, Y = -C ^ and E! E! E £ Bl -CH? OCH3 3-OCH2OCH? TMS 4- SCH2CH = CH? 3-S (0) CF2CF3 -CsC-OCH3 4-SCN 3-CC-TMS 3- (I-Ph-2.2-Di-Cl- or Pr) -C = CI 3-Ge (Me)? CF3 3-OSi (Me) 2Ph 3- (2-Me-4-Ph-c-Hex) -ada 3-Si (Me) 2CF3 2-OH 3-C "C-OTHP -CH2S -« - Pr 3-Ge (CF3) 3 2-N (Me) Bzl 3-OCH? CF = CF2 -SC «CEt 3-SCH? O -I 3 -SCH2OMe 3-SCH2SEt -OGeíMe ^ Ph 3- (C (= 0) (3-Me-Bzl)) 4-C (= S) Me 4 - ((4-F-Bzl) -0C (= O)) -C (= S) OEt 4-C (= S) SCHF? 2-C (= 0) N (Me)? 2-C (= S) N (Et) 2 -CH2CN 3-0C (= 0) Me 3-0C (= S) Me 4-SC (= 0) Me -NHC (= 0) Me 4-NHC (= S) Ph 4-0C (= 0) 0-oHex 4-OC (= 0) S - «- Pr -SC (-0) OCH2CF3 2-SC (-0) SMe 4-S (0) 2OCH2CF3 4-S (0)? N (Me) 2 - (NHS02 (4-Me-Ph)) 4- (0CH? (4-TMS-Ph)) 2-CH? OCH2 (2,4-Di-F-Ph) 4 - ((4-TMS-Ph) -CmC) - (S- (4-TMG-Ph)) 4-S (0)? Ph 3- (SCH? (3-Me-Ph)) 3- (4- pyrimidU-CH2) - (4-pyrimid? I -CEC) 3- (2-pyrimidiI-S) 4- (2-thienyl-CH?) 4- (2-tienU -S) - (2-furanU-0) 4- (3-furanU-S) 2- (4-pyrimidinU-CH?) 2- (2-pyrimidin-S) -0C »CCH 3 4-0CH? CH? OMe 3-OCH SMe 3-S (0)? CH2CH2CF3 -S (0) 2CF3 2-NH? 4-C (= S) OEt 2-C (= NH) OMe 2-0C (O) N (Me) Ph 3-OS (0)? CH 3 3- (4-CN-Ph) -OCH 2) - (2 -furanU-CH?) 3- (2-thiazoyl-CH?) 3 - ((3-CF3-4-pyrimidyl-OCH?) ) - - UTILITY / FOR ULATION The compounds of this invention will generally be used as a formulation or a composition with an agriculturally suitable carrier which comprises at least one liquid diluent., a solid diluent or a surfactant. The formulation or composition of the ingredients were selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors, such as soil type, humidity and temperature. Some formulations include liquids such as solutions (which include emulsifiable concentrates), suspensions, emulsions (including microeulsions and / or suspoemulsions) and the like which can be optionally condensed in gels. Some suitable formulations also include solids such as powder, granules, pills, tablets, films and the like that can be dispersed in water. ("mixable with water") or soluble in water. The active ingredient can be (micro) encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of the active ingredient can be encapsulated (or "coated"). The encapsulation can control or delay the release of the active ingredient. Some spray-type formulations can be extracted in a suitable medium and used as sprayed in volumes of about one to hundreds of liters per hectare. High strength compositions are used primarily as intermediates for the formulation. The formulations will typically contain effective amounts of the active diluent and surfactant within the following approximate ranges which add more than 100% by weight. % in weigh - A -t - y ... Diluent Surfac * -inte Dispersible in water and soluble PG, agii- 5-Qr 0-94 i-i? Granules, tablets and powder. Suspensions, emulsions, sulucion-f 5-r, "40-95 0-15 { Which includes emulsifiable tablets Powder l-_c; 70-9? 0-5 Pills and granules 0.01- °° 5-99.99 0-15 Composition of another firmness 0 __o 0-10 0-_! Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Cald ell, New Jersey. Typical liquid diluents are described in Mardsen, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp. , Ridgewood, New Jersey, in addition to Sisely and Wood, Encyclopedi a of Surfece Acti ve Agents, Chemical Publ. Co.mine. , New York, 1964, the list of - -surfactants and recommended uses. All formulations may contain minor amounts of additives to reduce foam, corrosion, microbiological growth or thickeners to increase viscosity. Some surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, fatty acid polyethoxylated ester sorbitan, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulphonates, organosilicon, N-N-dialkyltauranes, lignin sulphonates, condensates of forraaldehyde sulfonate naphthalene, polycarboxylates, polyoxyethylene / polyoxypropylene block copolymers. Some solid diluents include, for example, clay such as bentonite, montmorillonite, attapulgite and kaolin, starch, azicar, talc, silica, diatomaceous earths, urea, calcium carbonate, sodium carbonate and sodium bicarbonate and sodium sulfate. Some liquid diluents include for example, water, N, N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidine, ethylene glycol, propylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, olive oils, castor oil, flaxseed, sesame, corn, peanut, soybeans, coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and alcohol tetrahydrofuryl. Some solutions include emulsifiable concentrates, which can be prepared by mixing ingredients. The powders can be prepared by mixing and, usually when grinding as in a hammer mill or a fluid mill with energy. The suspensions are usually prepared by wet milling; see for example U.S. 3,060,084. The granules and pills can be prepared by spraying the active material in preformed granular carriers or by agglomeration techniques. See Browining, "Agglomeration," Chemical Engineering, December 4, 1967, pp. 147-48, Perry's Chemi cal Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57. The pills can be prepared as described in U.S. 4,172,714. The water-dispersible and water-soluble granules can be prepared as described in U.S. 4,144,050, U.S. 3,920,442 and DE 3, 246,493. The tablets can be prepared as described in U.S. 5,180,587, U.S. 5,208,030, the films can be prepared as described in GB '2,095,558 and U.S. 3, 299,556. For more information on the art of formulation, see U.S. 3,235,361, Col. 6 line 16 to Col. 7 line 19 and Examples 10-41, U.S. 3,309,192, Col. 5, line 43 to 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 to Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Sci ence, John Wiley and Sons, Inc., Blackwell Scientific Publications, Oxford, 1989. In the following Examples, all percentages are by weight and all formulations are prepared in conventional manners. The numbers of the compounds refer to the compounds in the Table Index A-C.

Example A Mixible powder with water Compound 39 65.0% Ether glycol polyethylene dodecifenol 2.0% Sodium ligninsulfonate 4.0% Sodium silicoaluminate 6.0% Montmorillonite (calcined) 23.0% Example B Granules Compound 39 10.0% Granules attapulgite (low volatility, 0.71 / 0.30 mm; Sieve U. S. No. 25-50) 90.0% Example C Extruded tablets Compound 39 25.0% Anhydrous sodium sulfate 10.0% Raw calcium ligninsulfonate 5.0% Sodium alkylnaphthalenesulfonate 1.0% Calcium / magnesium bentonite 59.0% Example D Emulsifiable concentrate Compound 39 20.0% Sulfonates soluble oil mixture And polyoxyethylene ethers 10.0% Isoform 70.0% The compounds of this invention are usually agents for controlling the killing of plants. The present invention further comprises a method for controlling the death of plants caused by plant fungal pathogens comprising the application to the seed of the plant or some portion to protect it, as well as to the plant born from the seed, an effective amount of a compound of this invention or a fungicidal composition containing a above-mentioned compound. The compounds and compositions of the present invention provide control of deaths caused by a large spectrum of fungal pathogens in the classes of Bacidiomycete, Ascomoceta, Oomyceta and Deutoromiceta. They are effective in controlling a broad spectrum of plant kill, particularly foliar pathogens from ornamental, vegetable, field, cereal and fruit crops. These pathogens include: Plasmopara viticola, Phytophtora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, Alternating brassicae, Septoria nodorum, Septoria tritici, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Piricularia oryzae, Podosphaera leucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recodida, Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Puccinia arachidi s, Rhizoctonia solani, Sphaerotheca fuliginia, Fasari um oxysporum, Verticilli um dahliae, Pythium aphanidermatum, Phytophthora megasperma, Sclerotinia sclerotiorum, Scl erotium rolfsii, Erysiphe polygoni, Pyrenophora teres, Gaeumannomyces graminis, Rynchosporium secalis, Fusarium roseum, Bremia lactucae and other genera and species closely related to the pathogens mentioned above. The compounds of this invention also exhibit an activity against a broad spectrum of food, foliar fruit, cane, root, seed, aquatic arthropods (the term arthropod includes insects, ticks and nematodes) which are growth pests and - agronomic crops, forestry, greenhouse crops, ornamentals, nursery harvest, storage of food and fiber-based products, livestock and the health of the public and animals. It can be seen that not all compounds are equally effective against all the growth states of all pests. However, all the compounds of the invention show an activity against pests that include: eggs, larvae and adults of the order Lepidoptera; egg, foliar, fruit, root, seed and adult food larvae of the order Coleoptera; immature eggs and adults of the hemiptera and Homoptera orders; eggs, larvae, chrysalises and adults of the order Acari; eggs, immature and adults of the orders Tisanoptera Ortóptera and Dermaptera; eggs, immature and adults of the order Diptera; and young and adult eggs of the Phylum Nematoda. The compounds of this invention are also active against pests of the orders Himenoptera, Isoptera, Sifonaptera, Blattaria, Tisonura, and Psocoptera; pests belonging to the class Arachnida and filum Platihelmintas. Specifically, the compounds are active against southern corn worms (Diabrotica undecimpunetata Howardi), skipjack (Macrosteles fascifrons), pod weevil (Anthonomus grandis), spider two spots (Tetranychus urticae), armyworm (Spodoptera frugiperda), aphid black bean (Aphis fabae), green peach aphid (Myzus pérsica), cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis noxia) English grain aphid (Sitobion avenae), tobacco budworm (Heliothis Virescons), rice weevil (Lissorhoptrus orizophilus), rice leaf beetle (Oulema oryzae), grasshopper of white loin (sogatella furcitera) , green leafhopper (Naphottetix cincticeps), grasshopper of coffee plant (Nilaparvata luguns), small brown grasshopper (Laodelphax striatellus), barrenillo de tronco de arrcz (Chilo Suppressalis), rice leaf flatten (Cnaphalocrocis medinalis, black stinky rice insect (Scotinophara landú), stinky rice insect (Ocbalus pugnax), rice bug (Leptocorista chinensis), thin rice insect (Cletus puntiger), and southern green stink insect ( Nezara viridula) The compounds are active in ticks, demonstrating ovicidal, larvicidal and chemosterilant activity against families such as Tetranychidde, urticae Tetranychus, Cinnabarinus Tetranychus, mcdanieli Tetranychus pacificus Tetranychus, turkestani Tetranychus, rubrioculus Byrobia, Panonychus ul i, Panonychus citri, Eotetranychus carpini borealis, Eotetranychus, hicoriae, Eotetranychus sexmaculatus, Eotetranychus yumensis, Eotetranychus banski and Oligonychus pratensis; Tenuipalpide that includes Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpus obovatus; Eriophyidae that includes Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae.

See WO90 / 10623 and WO 92/00673 for more detail in descriptions of pests. The compounds of this invention can be mixed with one or more other fungicidal, nematicidal, bacterozidal, acaricidal, growth regulating, chemosterilant, semi-chemical, repellent, attractant, pheromone, feed simulant or other biologically active insecticides to form a multicomponent pesticide giving a broad spectrum of agrucultural protection. Examples of such agricultural protectants with the compounds of the present invention can be formulated: insecticides such as abamectin, acephate, azympho-methyl, bifenthrin, buprofezin, carbofuran, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, cyhalothrin, lamda-cilothrin , deltamethrin, diafentiuron, diazinon, diflubenzuron, dimethoate, esfenvalerate, fenoxicarbon, fenpropatrin, fenvalerate, fipronil, flucitrinate, tau-fluvalinate, fonofos, imidaclopride, isophenofos, malathion, metaldehyde, methamidophos, metidation, methomyl, methoprene, methoxychlor, methyl 7- chloro-2, 5-dihydro-2 [[N- (methoxycarbonyl) -N- [4- (trifluoromethoxy] phenyl] amino] carbonyl] indene [1,2-e] [1,3,4] oxadiazine-4a ( 3H) -carboxylate (DPX-JW062), monocrotophos, oxamyl, parathion, patration-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pyrimicarbon, profenofos, retenone, sulprofos, tebufenozide, tefutrin, terbufos, tetrachlorvinphos, thiodicarbon, tralometrine, triclorphone, and triflumuron; fung such as azoxystrobin (ICIA5504), benomyl, blasticidin-S, Bordeaux mixture (tribasic cooper sulphate), bromoconazole, captafol, captan, carbendazim, chloronebo, chlorotanolil, cooper oxychloride, toner salts, cymoxanil, ciproconazole, cyprodinil (CGA 219417), diclomezine , dicloran, difenoconazole, dimethomorph, diniconazole, diniconazole-M, dodine, ediphenphos, epoxiconazolo, (BAS 480F), fenarimol, fenbuconazole, fenpiclonil, fenpropidin, fenpropimorph, fluazinam, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetil-aluminio, furalaxyl, hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamicin, kresoxim-methyl (BAS 490F), mancozeb, maneb, mepronil, metalaxyl, metconazole, S-methyl 7-benzothiazolocarbothionate (CGA 245704), 5-methyl-5- - - (4-phenoxyphenyl) -3-phenylamino-2, -oxazolidinedione (DPX-JE874), myclobutanil, neo-asozin (ferric metanearsonate), oxadixil, penconazole, pencicuron, probenazole, prochlorazo, propiconazole, pirifenox, piroquil on, sulfide, tebuconazole, tetraconazole, thiabendazole, thiophanate-methyl, thiram, triadimefon, triadimenol, tricyclazol, triticonazole, validamicin and vinclozolin, nematocides such as amitraz, chinomethionate, lorobenzilate, cyhexatin, dicofol, dienochlor, enazaquin, fenbutanin oxide, fenpropatrin, ~ enpyroximate, hexitiazoxo, propargite, pyrazole and tebufenpirada; and biological agents such as Bacillus thuringiensis, Bacillus thuri gi ensis delta endotoxin, baculovirus, and ento-opatogenic bacteria, viruses and fungi. On some occasions, combinations with other fungicides or arthropodicides having a similar spectrum of control but a different mode of action will be particularly advantageous for managing resistance. Preferred for better control of the death of plants caused by fungal pathogens (eg, lower use ratio or broad spectra of controlled plant pathogens) or resistance management are mixtures of a compound of the present invention with a fungicide selected from the group cyproponazole , copronidil, (CGA 219417), epoxiconazole (BAS 480F), fenpropidin, phenpropimorph, flusilazole and tebuconazole. Specifically preferred mixtures (the numbers of compounds refer to compounds in the Index of tables A-C) are selected from the group: compound 9 and ciproconazole; compound 9 and cyprodinil (CGA 219417); compound 9 and epoxiconazole (BAS 480F); compound 9 and fenpropidin; compound 9 and phenpropimorph; compound 9 and fusilazole; compound 9 and tebuconazole; compound 12 and ciproconazole; compound 12 and cipronidil ((CGA 219417), compound 12 and epoxiconazole (BAS 480F), compound 12 and fenpropidin, compound 12 and phenpropimorph, compound 12 and fusilazole, compound 12 and tebuconazole, compound 39 and ciproconazole, compound 39 and cipronidil (CGA) 219417), compound 39 and epoxiconazole (BAS 480F), compound 39 and fenpropidin, compound 39 and phenpropimorph, compound 39 and fusilazole, compound 39 and tebuconazole, compound 45 and ciproconazole, compound 45 and cipronidil (CGA 219417), compound 45 and epoxiconazole; (BAS 480F), compound 45 and fenpropidin, compound 45 and phenpropimorph, compound 45 and fusilazole, compound 45 and tebuconazole, compound 53 and ciproconazole, compound 53 and cipronidil (CGA 219417), compound 53 and epoxiconazole (BAS 480F); and fenpropidin, compound 53 and phenpropimorph, compound 53 and fusilazole, compound 53 and tebuconazole, compound 54 and ciproconazole, compound 54 and cipronidil (CGA 219417); compound 54 and epoxiconazole (BAS 480F); compound 54 and fenpropidin; compound 54 and phenpropimorph; compound 54 and fusilazole; compound 54 and tebuconazole; compound 103 and cyproconazole; compound 103 and cipronidil (CGA 219417); compound 103 and epoxiconazole (BAS 480F); compound 103 and fenpropidin; compound 103 and phenpropimorph; compound 103 and fusilazole; compound 103 and tebuconazole. The control on the mortality of the plants is ordinarily carried out by the application of an effective amount of a compound of this invention either before or after the infection to a portion of the plant that will be protected as the roots, fruits, seeds foliage, stem, tubes or bulbs or the average (spot or sand) in which the plants to be protected are growing. The compounds can be applied on the seed to protect the seed and the tree. For the control in the mortality of the plant, percentages of the application of these compounds can be influenced by many environmental factors and could be determined under current conditions. The foliage can be protected normally when it is a portion or less than 1 g / ha to 5000 g / ha of active ingredient. The seeds can be normally protected when they are treated with a portion of 0.1 to 10 g per kilogram of seed.

Arthropod type pests are controlled and protected, agronomic, horticultural and special crops, the health of humans and animals is carried out by applying one or more of the compounds of the invention, in an effective amount, in the environment pests include agronomic and / or non-agronomic sites of infestation, to the area not being protected or directly to The pests to be controlled. In this manner, the present invention further comprises a method for the control of foliar arthropods and nematode earth and pests and the protection of agronomic and / or non-agronomic crops, comprising the application of one or more of the compounds of the present invention, or compositions containing at least one compound, in an effective amount to the environment of pests including agronomic and / or nonagronomic sites of infestation, to the area to be protected or directly in the parts to be controlled. A preferred method of application is in the form of sprinkling. Alternatively, granular-type formulations of these compounds can be applied to the foliage of the plant or to the soil. Other methods of application include direct and residual sprays, aerial sprays, seed coatings, microcapsulations, baits, boluses, fimugantes, aereosols, powders and many others. The compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like. For the control of arthropod pestsThe compounds of this invention can be applied in their pure state, but the majority of the applications will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated use. A preferred method of application is the application in the form of spraying a water dispersion or a refined oil solution of the compounds. Combinations with aerosol oils, aerosol oil concentrations, adipose spraying tips, other solvents and synagogues such as piperonyl butoxide frequently increase the compound's effectiveness. The percentage of application required for an effective control will depend on some factors such as the Arthropod species to be controlled, the life cycle of the pests, state of life, c size, location, time of year, animal or harvest host, behavior of forage, mating behavior, humidity of the environment, temperature and the like. Under normal circumstances, the application of percentages of about 0.01 to 2 Kg of active ingredient per hectare may be sufficient to control pests in agronomic ecosystems, but as 0.001 Kg / hectare may be sufficient or as much as 8 Kg / hectare may be required. For non-gastronomic applications, effective percentages may be in the range of about 1.0 to 50 mg / m2 may be required. The following tests will demonstrate the efficiency -.the control of the compounds of this invention in pests of pathogens and arthropods. For tests on erropod pests the "control efficiency" represents the inhibition in the development of arthropods (including mortality) that significantly reduces forage. The control of the pathogenic and arthropod plague provided by the compounds is not limited, for the species. See the Table A-C index for the descriptions of the compounds.

- - The following abbreviations are used in the tables of the index and are the following: t = tertiary, c = cycle, Me = methyl, Et = ethyl, Bu = butyl, Ph = phenyl, Meo and oMe = methoxy, Eto = ethoxy , Pho = phenoxy, Phs = phenylthio, CN = cyano, N02 = nitro, Me3Si = trimethylsilyl and CHO = formyl. The abbreviation "dec" indicates that the compound appeared to decompose or melt. The abbreviation "EX" is for "Example" and is followed by a number indicating which Example the compound is prepared.

INDEX TABLE A Cropd No. y_ m, p, (° c) 1 Ex. 18 CH2ON = (Me) 4-HO-Ph? NMR See table index C for data 1 HNHR.

INTMCF. FROM TABLE B Creation o. X B &Y m m.a CO 2 MeO H CH 2 S 3- (MeOC (= NH) > -6- (MeC (-0)) -2- 190 (dec) pyridinyl 3 MeO H CH 2 S 3 -CN-6- (MeC ("0) > 2- pyridinyl 105-1 10 4 MeO H CH2S 3-CN-6- (MeC (OMe) 2) -2- pyridinyl 1 0 (dec) Cl H CH 2 S 3-CN-6-. { MeC (= 0) > 2- pyridinyl 143-148 6 Cl H CH 2 S 3-CN-6- (CH 3 C (OMe) 2) -2- pyridinyl 117-123 7 Ex. 1 1 Cl H O 3-HO-P 135-138 S Ex. 12 MeO H 0 3-HO-Ph 153-155 9 Ex. 3 MeO H 0 3- (1, 3-benzodioxol-5-yl) - 1,2,4- 168-169 riadiaznl -5-yl 10 MeO H 0 2-NH 2 3- (2-Me- PhO) -Ph 72-75 11 Ex.4 MeO H or 5- (1-ad amanil) - 1, 3, 4-oxadiazol-2-yl * 12 Ex. 21 MeO H CH2ON-C (Me) 3-ÍCF3CH2CH2SiMe2) -Ph oil * 13 MeO H CH2ON = C (Me) 3- (4-Me3Si-PhCH20) -Ph oil * 14 Cl H CH 2 3,5-dMe-4- (2-pyrimidinyl S) -? H-154-156 pyrazole-1-yl 15 to H CH 2 ON = C (Me) 3- (4-Me 3 Si- PhCH20) -Ph oil * 16 MeO H O 3- (PhCH20 Ph 98-100 17 MeO H O 3- (c-hexyl-0) -Ph oil * 18 MeO H CH2ON = C (Me) 4- (PhCH20C (= 0) 2-pyridinyl 130-132 19 MeO H 0 3-NH2-6-Cl-2-pyridinyl 163-166 0 MeO HO 3-PhS-Ph oil * 1 MeO H 0 3- (4-CI-PhCH20> -Ph oil * 2 MeO H 0 3 - (2,4-dtCI-PhCH20) -Ph oil * 3 MeO H 0 3- (2-CF3-PhCH20) -Ph oil * 4 MeO H 0 3- < 4-CF3-PhCH20) -Ph oil * 5 MeO H or 3- (2,5-dMe-PhCH20> -Ph oil * Cmpd No 2. R3a Y 26 MeO HO 3- (2,6-diF-PhCH20) -Ph oil * 27 MeO H O 3-. { 3-Me0-PhCH20) -Ph 128-131 28 MeO H O 3- (4-F-PhCH20) -Ph oil * 29 MeO H CH2ON = C (Me) 4-. { Me3Si-C - C) -2- pyridinyl oil * MeO H O 3- (2-Me-PhCH20) -Ph 104-105 31 MeO H O 3- (3-Me-PhCH20) -Ph oil * 32 MeO H O 3- (4-Me-PhCH20) -Ph oil * 33 MeO H O 3- (2-CN-PhCH20 > -Ph 97-98 34 MeO H O 3-í2-N? 2-PhCH20) -Ph 135-136 MeO H O 3-. { 3,5-diF-PhCH20 > Ph oil * 36 MeO H O 3-í2-F-PhCH20) -Ph oil * 37 MeO H O 3- (3-F-PhCH20) -Ph oil * 38 MeO H O 3-0-CF3-PhCH20) -Ph oil * 39 Ex. 13 MeO H O 3- (2-CI-PhCH20 > -Ph 1 12-114 40 MeO H O 3- (3-Cl-PhCH20) -Ph oil * 41 MeO H O 3- (3,5-d? Cl-PhCH20> Ph oil * 42 MeO HO 3- (2-pyridinyl-CH 20) -Ph oil * 3 MeO HO 3- (4-pyridinyl-CH 2?) - Ph oil * 4 MeO HO 3- (3,3-d? F-2-MeO -l-cyclohutene-l-yl oil * 1,2,4-thiadiazol-5-yl 5 Ex. 2 MeO HO 3- [1 - (4-Cl-Ph) -cyclopropyl J- 1, 2,4- 123 -124 thiadiazol-S-il 6 MeO HO 3- (1-Ph-cyclopropyl) -1,4-thiadiazole-solid * 5-yl 7 Ex. 10 MeO HO 3 - ((EtO) 2CH) -l_2, 4- thiadiazol-5-yl 8 MeO HO 3- (1_2,3,4-tetrahydro-oil * 1- naphthalenyl -0) -Ph 9 MeO HO 4-Cl-5-CHO-2-thiazolyl 98-101 0 MeO 6-Me O 3- (2-F-PhS) -Ph oil * 1 MeO HO 3- {4-F-Ph-C «C> - 1.2,4-thiadiazole -5- U 2 Ex. 1 MeO HO 3- (2-pyridinyl -C "C) -1,2,4-thiadiazol-5-yl 3 Ex. 20 MeO H CH2ON <: (Me) 3 - ((CF3) 3Ge Ph oil * 4 Ex 14 MeO 6-Me O 3- [l- {4-Cl-Ph c'clopropU] -l, 2,4- 119-121 thiadiazole-5-yl 5 MeO 4 -MeO O 3- [l- (4-C! -Ph) -cyclopropyl J-1,2,4- 150-151 rindiazol-5-yl C Dd No. X. 3a Y 56 MeO 6-Me 0 3 - (I -Ph-cyclopropyl) - 1,2,4-thiadiazole - 138-141 5- il 57 MeO 4-MeO O 3- (l-Ph-cyclopropyl) - 1,2,4-thia diaz? l - oil * 5- il 58 MeO H O 3- (2-Cl-4-F-PhCH20) -Ph oil * 59 MeO H 0 3- (2, i-diF-PhCH20) -Ph 83-86 60 MeO H or 3- (2,3-diF-PhCH20) -Ph oil * 61 MeO H or 3- (3,5-d¡Cl-PhOCH2) -Ph oil * 2 MeO H or 3- (4-thiomorpholinyl • CítjH'h oil * 3 MeO H or 3- (2-naphthalenyl -CH2 > -1.2,4-thiadiazole-5-yl 4 MeO H or 4-CI-5-C (0) NH2-2- thiazolyl solid * 5 MeO H 0 3- </ -BuC (-0) 0) - 1, 2,4-thiadiazol-5-yl 137-138 6 Ex. 5 MeO H or 3- (2-Cl-P CH 0) -1,2,4-thiadiazol-5-yl 107-108 7 Ex. 19 MeO H 0 3- (CF3S (0> 2?) - Ph oil * 8 MeO H CH2ON = C (Mc) 3 - (? HCH20) -Ph oil * 9 MeO HO 4- (3-CF3-Ph) -5-C? 2H-2-thiazolyl 204-205 (dec) 0 MeO H CH2ON «C (Me) 3- (HC * CCH20) -Ph oil * 1 Ex. 17 MeO H CH2ON = C (Me) 3- (/ -BuOC (= 0) CH20) -Ph oil * 2 MeO HO 3- [3,5- (CF3S (0) 20) 2-Ph] -, 4-thiadiazole -5- i) 3 MeO H CH2ON- C (Me) oil * 3- (Me0C (-O) CH2O) -Ph 4 MeO HO 3 - ((EtO) 2CHC-sC> .Ph oil * 5 MeO HO 4- (3,5-diCF3-Ph) -5-CHO-2- thiazolyl solid * 6 MeO HO 3 - ((EtO) 2CHCBC>, 4-thiadiazole -5- 55-58 il 7 MeO H 3 - ((/ - BuO) 2CHC-? C) - 1, 2,4-thiadiazole-115-116 5-il 8 Ex. 9 MeO H 0 3- (CF 3 S (0) 2?) - 1, 2,4-thiadiazol-5-yl 9 MeO H 0 3- ( 2,5-diCt-PhS (0) 20> 1, 2,4-ti adiazole -5_ il 0 MeO H O 3- (4-Br-PhS (0) 2?) - 1, 2,4-thiadiazol-5-yl 1 MeO H 0 3-. { Me 2 C (OH) Ca! C) -Ph 165-167 2 MeO H O 3 - ((/ - BuO) 2CHC «C) -Ph oil * Cmpd No. X. Bll m.t > .ra 83 MeO HO 3- (Me 2 C (OH) C * C) - 1.2.4- thiadiazole -5- oil * il 84 MeO H 0 3- (bicyclo [4.2.0] octale, 3,5-triep-7"U) - 139-140 1 -2,4-thiadiazole-5-yl 85 MeO H 0 3- (Ph 2 C (Me)) - 1, 2,4-thiadiazol-5-yl solid * 86 MeO H 0 3- (4-Br-Ph-C (Me) 2) - 1,2,4-thiadiazole - solid * 5- il 87 MeO H 0 3- (2- naphthalene-CÍMe ^) - 1,2,4-solid * thiadiazole-5-yl 88 MeO HO 3- (3,5-diF-Ph-C (Me) 2) -1,4,4-thiadiazoI-5-yl 89 MeO H 0 3- (3,5-diCF3- Ph-C (Me) 2) -, 4-thiadiazole-5-U 90 MeO H 0 3- (3-CF 3 -F-C (Me> 2) -l, 2,4-oil * thiadiazole-5- Il 1 Ex. 6 MeO HO 3- (Me 2 C (CN)) - 1, 2,4-thiadiazol-5-yl solid * 2 MeO HO 3- (3-Cl-Ph-C (Me) 2) -1, 2,4-thiadiazol-5-yl 3 MeO HO 3- (3-MeO-Ph-C (Me) 2) - 1, 2,4-oil * thiadiazole-5-yl 4 MeO HO 3- (4-Cl) -Ph-C (Me) 2) - 1,2,4-thiadiazole • 5-yl 5 MeO 6-Me O 6- (1 H-mdazol-1-yi-4-pyrimidinyl 175-179 6 Ex. 7 MeO HO 3- (PhCH20) -, 4-thiadiazol-5-yl • 7 Ex. 8 MeO HO 3-HO-l, 2,4-thiadiazole -5- ü oil * 8 Ex. 15 Cl H CH2ON-C (Me) 3-HO-Ph oil * 9 Ex. 16 M eO H CH2ON = C (Me) 3-HO-Ph oil * 100 MeO HO 3- (4-Cl-PhOC (Me) 2) -1,2,4-thiadiazol-5-yl 101 MeO 6-Me O 3- (Me 3 SiD-C>, 2,4-thiadiazole - 5- il 02 MeO HO 3- (Me3S¡C «C) -l, 2,4-thiadiazole -5- U 03 MeO HO 3- (Me3SiC« C) -Ph 04 MeO HO 6- (2-Cl-PhCH20 ) -4- pyrimidinyl 133-135 05 MeO 6-Me O 6- (2-Cl-PhCH20) -4- pyrimidinyl 135-137 06 MeO 6-Me O 6- (3,5-d? F-PhCH2? H -pyrimidinU oil * 07 MeO 6-Me O 6- (2_3-d¡F-PhCH2OH- pyrimidinyl oil * 08 MeO HO 6- (2,4-diF-PhCH2OH- pü-iit? dinil oil * Cmod No. 2_ s2 ? mP- CC 109 MeO H 0 6- (2,3-diF-PhCH20) -4- pyrimidinU oil * 110 MeO H 0 6- (2-Cl-PhCH2CH20) -4- pyrimidinyl oil " 11 1 MeO 6-Me O 6- (2-Cl-PhCH2CH2?) - 4-pyrimidinyl oil * 1 12 MeO H 0 6- (4-Me-PhCH20) -4- pyrimidinyl oil * 113 MeO 6-Me 0 6-í4-Me-PhCH20) -4- pyrimidinyl oil * 114 MeO H 0 6- (2,4-diCl-PhOCH2CH2?) - 4- oil * pyrimidinyl 115 MeO 6-Me 0 6- (2,4-diCl-Ph0CH2CH2O) -4- oil * piriniidin.il 116 MeO HO 6- (3,5-diCF3-PhCH2?) - 4-pyrimidinyl oil * 117 MeO 6-Me O 6- (3,5-d? CF3-PhCH20) -4- pyrimidinU 141-143 118 MeO H 0 6- (3-CF3-PhCH2CH2OH- pyrimidinU oil * 119 MeO 6-Me O 6-y3-CF3-PhCH2CH20) -4- pyrimidiumU oil * 120 MeO H 0 6- (1-naphthalenyl-CH 2 CH 20) -4- oil * pyridinediyl 121 MeO 6-Me O 6- (1-naphthalenyl .CH 2 CH 2?) - - oil * piyniidinyl 122 MeO HO 6- (4-pyridinyl CH 2 O ) -4 * pyrimidinyl oil * 123 MeO 6-Me O 6. (4- pyridine-pyrimidinyl oil * 24 MeO H 0 6- (MeOCH2CH20) -4- pyrimidinU oil * 125 MeO 6-Me 0 6- (MeOCH2CH20) -4- pyrimidine oil * 26 MeO 6-Me 0 6- (2-Me-PhCH2OH- pyrimidinU oil * 27 MeO 6-Me O 6- (3-Cl-PhCH? S) -4- pyrimidinU oil * * See Table C Index for data 'H NMR TABLE INDEX C Cmpd No.' H NMR data (solution of CDCI ^ unless otherwise indicated) * 1 d 7.52 (d, lH), 7.42 (m, 2H), 7.32 (m, 2H), 6.72 (m, 3H), 5.24 (AB q_2H), 3.94 (d, 3H), 3.44 (d, 3H) .2.16 (d, 3H). 1 1 d 7.8 (d, lH), 7.5 (t, lH), 7.42 (m, 2H), 3.86 (s, 3H), 3.44 (s.3H), 2.1 (br s, 3H), 2.04 (br m , 6H), 1.79 (br m, 6H). 12 d 7.7 (s, lH), 7.6 (m_2H), 7.4-7.5 (m, 3H), 7.4 (t, lH), 72 (d-2H), 5.2-5.3 (q_2H), 3.882 (s, 3H) , 3.401 (s, 3H), 2.201 (s, 3H), 2.0 (m_2H) - 1.0 (m_2H), 0.32 (s, 5.5H). 13 d 7.6 (m, 3H), 7.4 (m, 4H), 7.2 (d, 1 H), 6.9 (d, lH), 5.2 (q ^ H), 5.061 (s-2H), 3868 (s, 3H) ), 3.405 (s, 3H), 2.174 (s, 3H). 0271 (s, 7H). d 7.5-7.6 (m, 5H), 74 (t, 3H), 7,226 (s, 2H), 7.15 (d.lH), 6.9 (d, lH), 5.1-5.3 (q, 2H), 5,058 ( s, 2H), 3.463 (s, 3H), 2.156 (s, 3H), 0.271 (s, 9H). 17 d 1.2-1.4 (m.3H) .1.4-1.6 (m, 2H), 1.7-1.8 (m.3H), 1.9-2.0 (m ^ H), 3.39 (s.3H), 3.86 (s.3H) ), 4.2 (m, lH), 6.5-6.6 (m, 2H), 6.65 (m.lH), 7.0 (m, lH), 7.2 (m, 2H), 7.3-7.4 (m, 2H). 20 d 3.38 (s, 3H), 3.80 (s, 3H), 6.8-6.9 (m, lH), 6.9-7.1 (m, 2H), 7.2-7.4 (m, 10H). 21 d 3.38 (s, 3H), 3.85 (s, 3H), 4.99 (s, 2H), 6.6 (m_2H), 6.7 (m.lH), 7.0 (m.IH), 7.2 (m, 2H), 7.3 -7.4 (m, 6H). 22 d 3.38 (s, 3H), 3.85 (s, 3H), 5.08 (s_2H), 6.65 (m-2H), 6.75 (m.lH), 7.0 (m.lH), 7.2-7.3 (m, 3H) , 7.3-7.4 (m, 3H), 7.50 (m.lH). 23 d 3.38 (s, 3H), 3.84 (s, 3H), 5.23 (s, 2H) .6.6-6.75 (m, 3H) .7.0 (m.lH), 7.2 (m, 2H), 7.3-7.5 ( m.3H), 7.6 (.lH), 7.7 (m-2H). 24 d 3.37 (s, 3H), 3.85 (s, 3H), 5.08 (s, 2H), 6.6-6.7 (m, 2H) .6.7 (m.lH), 7.0 (m.lH), 7.2-7.3 ( m, 2H), 7.3-7.4 (m, 2H), 7.52 (d, J = 8.l HzJH), 7.62 (dJ = 8.2 HZ.2H). 25 d 2.31 (s, 3H), 2.32 (s, 3H), 3.39 (s, 3H), 3.85 (s, 3H), 5.30 (s, 2H), 6.6 (m, 2H) .6.68 (m, lH) , 6.75 (rn.lrT), 7.0-7.1 (tp, 3H), 7.2 (m, 3H), 7.35-7.40 (m, 2H, 26 d 3.38 (s, 3H), 3.84 (s, 3H), 5.07 ( s, 2H), 6.6-6.7 (m, 2H) .6.75 (m.lH), 6.9 (p H), 7.05 (m.lH) .7.2-7.3 (m, 2H), 7.3-7.4 (m.3H 28 d 3.38 (s, 3H), 3.85 (s, 3H), 4.97 (s, 2H), 6.6-6.7 (rn, 2H) .6.75 (m.lH), 7.0-7.1 (m, 3H), 7.2-7.3 (m, 2H), 7.3-7.4 (m, 4H), 29 d 8.50 (d, lH), 7.80 (s, lH), 7.60 (d, 1H), 7.50-7.40 (m_2H), 7.28- 7.24 (m, 2H), 5.3 (dd, 2H), 3.90 (s, 3H), 3.43 (s, 3H), 2.27 (s, 3H), 0.27 (s, 9H). 31 d 2.36 (s, 3H), 3.38 (s, 3H), 3.84 (s, 3H), 4.97 (s_2H), 6.6-6.7 (p H) .6.75 (m, lH), 7.0 (m.lH), 7.1-7.3 (ra, 6H), 7.3-7.4 (m, 2H). 32 d 2.35 (s, 3H), 3.38 (s, 3H), 3.84 (s, 3H), 4.97 (s, 2H), 6.6-6.7 (m, 2H) .6.75 (m, lH), 7.0 (rn. lH), 7.2-7.25 (, 4H), 7.3-7.4 (tn, 4H). 33 d 3.38 (s, 3H), 3.86 (s, 3H), 5.21 (s, 2H), 6.6-6.7 (m, 2H) .6.7 (m, lH), 6.75 (m.lH), 7.0-7.1 ( m.lH), 7.2-7.3 (m_2H), 7.35-7.50 (m, 3H) 7.6-7.8 (m_2H). d 3.37 (s, 3H), 3.86 (s, 3H), 5.00 (s, 2H), 6.6-6.8 (m, 4H), 6.9-7.0 (m, 3H), 7.2-7.3 (m, 2H), 7.3-7.4 (m, 2H). 36 d 3.38 (s, 3H), 3.84 (s, 3H), 5.08 (s, 2H), 6.6-6.7 (m, 2H), 6.75 (m, lH), 7.0-7.25 (m.5H), 7.3- 7.4 (m, 3H), 7.48 (m.lH). 37 3.38 (s, 3H), 3.85 (s, 3H), 5.01 (s, 2H), 6.6-6.7 (m-2H), 6.75 (ra.lH),, 7.0 (m-2H) .7.1-7.3 ( m, 4H), 7.3-7.4 (m, 3H). 38 d 3.38 (s.3H), 3.85 (s.3H) .5.06 (s_2H), 6.6-6.7 (m-2H), 6.75 (m.lH), 7.0 (m, lH), 7.2-7.3 (m, 2H) .7.3-7.4 (pUH), 7.5 (m.lH), 7.6 (m, 2H), 7.67 (m, lH). 40 d 3.38 (s, 3H), 3.85 (s, 3H), 4.99 (s, 2H), 6.6 (m, 2H), 6.7 (m, lH), 7.0 (m, lH), 7.2-7.4 (m, 8H). 41 d 3.38 (s, 3H), 3.86 (s, 3H), 4.96 (s-2H), 6.6-6.7 (m, 3H), 7.0 (rp.IH), 7.2-7.3 (m, 5H), 7.3- 7.4 (ra, 3H). 42 d 3.38 (s, 3H), 3.84 (s, 3H), 5.16 (s, 2H), 6.6 (m, lH), 6.7 (s.lH), 6.75 (m, lH), 7.0 (m, lH) , 7.2-7.3 (m_3H), 7.35 (m-2H), 7.5 (m, lH, 7.70 (m, lH), 8.6 (m, lH), 43 d 3.37 (s, 3H), 3.86 (s, 3H) , 5.04 (s, 2H), 6.6-6.65 (m_2H), 6.70 (m.lH), 7.0 (m.lH), 7.2-7.3 (m, 2H), 7.3-7.4 (m, 4H), 8.6 (dd) , Jl.5,4.5 Hz_2H). 44 d 7.54 (m_2H), 7.46 (irt-2H), 4.06 (s, 3H), 3.83 (s, 3H), 3.39 (s, 3H), 3.02 (m, 2H). 46 d 7.53 (m, 2H, 7.45 (m, 4H) .7.36 (m, 3H), 3.81 (s, 3H), 3. 1 (s, 3H), 1.65 (m, 2H), 1.35 (m, 2H 47 d 7.6-7.4 (m, 4H), 5.53 (s, lH), 3.81 (s, 3H), 3.8-3.65 (m, 4H), 3.40 (s, 3H), 1.23 (t, 6H). 48 d 1.8 (m.lH), 2.0 (m, 2H), 2.1 (m, lH), 2.7-2.9 (rn_2H), 3.38 (s, 3H), 3.85 (s, 3H), 5.35 (s, IH) , 6.6 (m, lH), 6.7 (, lH), 6.8 (m, lH), 7.0 (m.lH), 7.15-7.3 (m, 5H), 7.3-7.4 (m, 3H) 50 52.26 (s) , 3H), 3.39 (s, 3H), 3.81 (s, 3H), 6.8 (m_2H), 6.93 (U = 1.8 Hz, lH), 6.98 (d, J = 7.7 HzJH), 7.05-7.11 (m, 3H ), 72-7.4 (m, 4H), 51 d 7.6-7.55 (m, 4H), 7.5 (rp_2H), 7.1 (t, 2H), 3.84 (s, 3H), 3.40 (s, 3H). 52 d 8.65 (d, lH) .7.7 (ra.lH), 7.65-7.5 (mJH), 7.5-7.4 (m_2H), 7.3 (m, lH), 3.84 (s, 3H), 3.40 (s, 3H) . 53 d 7.941 (s, lH), 7.7 (d, lH), 7.55 (m-2H), 7.4-7.5 (m_2H), 7.4-7.5 (m-2H), 7.1 (t_2H), 5.2-5.4 (q_2H) , 3.889 (s, 3H), 3.413 (s, 3H), 2.152 (s, 3H). 57 d 7.44 (m, 2H), 7.32 (m, 4H), 7.09 (d, J-2.6 Hz, lH), 6.91 (d4J-8.8 ^ .6 HAIH), 3.81 (s, 6H), 3.40 (s, 3H), 1.65 (m_2H), 1.35 (m_2H). 58 d 3.38 (s, 3H), 3.85 (s, 3H), 5.09 (_-2H), 6.6-6.7 (itUH), 6.7-6.8 (m, lH), 6.9-7.1 (m-2H), 7.2- 7.3 (m_2H), 7.3-7.4 (m, 4H). 59 d 3.38 (s, 3H), 3.85 (s, 3H), 5.06 (s_2H), 6.6-6.8 (m, 3H), 6.95-7.05 (m, 4H), 7.2-7.3 (rn ^ H), 7.3- 7.4 (m, 2H). 60 d 3.38 (s, 3H), 3.85 (s, 3H), 5.09 (s_2H), 6.6-6.8 (m, 3H) .7.0 (m.lH), 7.1 (m_2H), 7.2-7.3 (m, 3H) , 7.3-7.4 (n H). 61 d 3.37 (s_3H), 3.85 (s, 3H), 4.99 (s_2H), 6.81 (m_2H), 7.0 (m, 3H), 7.05 (m, lH), 7.1-7.2 (_2H), 7.3-7.4 (m_3H ). 62 d 2.60-2.75 (m.8H), 3.38 (s.3H) .3.48 (s, 2H), 3.88 (s, 3H) .6.85-7.00 (m.3H), 7.07 (dJ-7.7 Hz, lH) , 7.15-730 (m.2H), 7.36 (dd.J = l.6.7.7 Hz_2H). 63 d 7.79 (m, 4H) .7.55-7.4 (m.7H), 4.28 (s_2H), 3.68 (s_3H), 3.37 (s, 3H). 64 67.55 (m, 2H), 7.45 (m, 2H), 3.87 (s, 3H), 3.40 (s_3H). 67 d 7.42 (rrOH), 7.3 (m, lH) .7.04 (m, 3H>, 6.96 (t.lH), 3.83 (s, 3H), 3.38 (m, 3H) .68 d 7.6 (rn.lH ), 7.4 (m, 7H), 7.24 (m, 4H), 6.86 (d, lH), 5.23 (sJH), 5.08 (q, 2H), 3.89 (s, 3H), 3.37 (s, 3H), 2.23 (s, 3H) .70 d 7.6 (m, 1H), 7.46 (m, 2H), 7.24 (m, 4H), 6.88 (m, 1H), 5.08 (q_2H), 4.785 (q, 2H), 3.92 ( s, 3H), 3.39 (s_3H), 2.48 (t, lH), 2.23 (s, 3H), 71 d 7.6 (m.lH), 7.45 (m_2H), 7.23 (m, 4H), 6.87 (m.lH ), 5.09 (AB q_2H), 4.63 (s_2H), 3.91 (s, 3H), 3.39 (s, 3H) .2.28 (s, 3H), 1.48 (s, 9H), 72 d 8.16 (s_2H), 7.60 ( m, 2H), 7.51 (m, 2H), 7.31 (m, lH), 3.84 (s, 3H), 3.38 (s, 3H), 73 d 7.61 (m, lH), 7.45 (m, 2H), 7.23 (m, 4H), 6.88 (m, lH), 5.075 (m_2H), 4745 (s, 2H), 3915 (s, 3H), 3.77 (s, 3H), 3.39 (s, 3H), 2.28 (s, 3H). 74 d 7.37 (m-2H), 7.25 (m, 3H), 7.11 (s.lH), 6.99 (, 2H), 5.46 (s, lH), 3.83 (s, 3H), 3.79 (m, 2H), 3.64 (m, 2H), 3.38 (s, 3H), 1.26 (t, 3H). 75 d 9.9 (s, lH), 8.15 (s_2H), 8.0 (s.lH) .7.6 (m, 2H.7.5 (m_2H), 3.9 (s, 3H), 3.4 (s, 3H) 78 d 7.6- 7.4 (m, 4H), 3.84 (s, 3H), 3.41 (s.3H), 79 d 8.06 (s, lH), 7.6-7.4 (m, 6H), 3.82 (s, 3H), 3.40 (s, 3H) .80 d 7.88 (d, 2H), 77-7.3 (m, 6H), 3.81 (s, 3H), 3.40 (s, 3H), 82 d 7.36 (d, 2H), 7.21 (m, 3H) , 7.08 (s, lH), 6.97 (d, 2H), 5.61 (s, lH), 3.84 (s, 3H), 3.38 (s, 3H), 1.35 (s, 18H), 83 d 7.55 (m, 2H) ), 7.46 (m_2H), 3.84 (s.3H), 3.40 (s.3H), 2.18 (s, lH), 1.60 85 d 7.55-7.40 (m, 4H), 7.29 (m, 3H), 7.25-7.20 (m, 7H), 3.62 (s, 3H), 3.39 (s, 3H), 2.18 (s, 3H), 86 d 7.52 (m, 2H), 7.42 (m, 4H), 7.22 (d-2H), 3.69 (s, 3H), 3.38 (s3H), 1.75 (s, 6H), 87 d 7.79 (m, 4H), 7.50-7.40 (m, 7H), 3.62 (s, 3H), 3.35 (s_3H), 1.88 (s, 6H). 88 d 7.53 (m-2H), 7.46 (m-2H), 6.85 (m, 2H), 6.65 (m, lH), 3.72 (s, 3H), 3.38 (s, 3H), 1.75 (s, 6H) . 89 d 7.80 (s, 2H), 7.74 (s, 1H), 7.50 (m_2H), 7.45 (m, 2H), 3.71 (s, 3H), 3.38 (s, 3H), 1.83 (s, 6H). 90 d 7.60 (S.1H), 7.51-7.41 (m, 7H), 3.66 (s, 3H), 3-38 (s, 3H), 1.80 (s, 6H). 91 d 7.57 (m, 2H), 7.48 (m, 2H), 3.83 (s, 3H), 3.40 (s, 3H), 1.77 (s, 6H). 92 d 7.50-7.40 (m, 4H), 7.30-7.20 (m, 4H), 3.67 (s, 3H). 3.38 (s, 3H), 1.76 (s.6H). 93 d 7.53 (m, 2H), 7.45 (m_2H), 7.21 (m.lH), 6.89 (m, 2H), 6.75 (d, lH), 3.77 (s, 3H), 3.64 (s, 3H), 3.38 (s, 3H), 1.77 (s.6H). 94 d 7.51 (m, 2H), 7.45 (m, 3H), 7. 26 (m, 3H), 3.68 (s, 3H), 3.38 (s, 3H), 1.76 (s, 6H). 96 d 7.6-7.3 (m, 9H), 5.37 (s_2H), 3.79 (s, 3H), 3.40 (s, 3H). 97 d 7.3-7.1 (m, 4H), 3.98 (s, lH), 3.89 (s, 3H), 3.41 WH). 98 d 8.09 (br s, lH), 7.62 (d, lH), 7.51 (m, 2H), 7.22 (m, 4H), 6.9 (d, lH), 5.08 (q, 2H), 3.44 (s, 3H) ), 2.25 (m, 4H). 99 d 7.6 (dd, lH), 7.45 (m_2H), 7.25 (m, 3H), 7.19 (tn-2H), 6.85 (dd, lH), 5.08 (AB q_2H), 3.92 (s.2H, 3.39 (s) , 3H), 2.24 (s, 3H), 100 d 7.49 (m_2H), 7.45 (m.2H), 7.15 (d, lH), 6.68 (d, lH), 3.80 (s, 3H), 3.37 (s, 3H), 1.75 (s, 6H), 101 d 7.42 (ml H), 7.30 (m, 2H), 3.82 (s, 3H), 3.40 (s, 3H), 2-29 (s, 3H), 025 ( s, 9H), 102 d 7.54 (m_2H), 7.46 (m, 2H), 3.83 (s.3H), 3.39 (s, 3H), 0.25 (s, 9H). 103 d 7.36 (m.2H), 7.22 (, 2H), 7.09 (s, lH), 6.98 (d-2H), 3.84 (s, 3H), 3.39 (s, 3H), 0.25 (s, 9H). 106 d 8.44 (s.lH), 7.43 (m.2H), 7.22 (m, lH), 7.1 1 (rn.lH), 6.86 (m, 2H), 6.22 (d, 1H), 5.43 (s, 2H) ), 3.78 (s, 3H), 3.33 (s, 3H), 2.27 (s, 3H). 107 d 8.44 (s.lH), 7.39 (m.h. H). 7.16 (xp, 5H), 6.24 (s.1H), 5.5 (s, 2H). 3.78 (s, 3H), 3.33 (s, 3H), 2.27 (s, 3H). 108 d 8.45 (m, lH), 7.39 (m, 5H), 6.86 (m_2H), 6.26 (m, 1H), 5.44 (s, 2H), 3.77 (s, 3H), 3.33 (s, 3H). 109 d 8.44 (s, lH), 7.32 (m, 7H), 6.27 (m, 1H), 5.51 (s_2H), 3.77 (s, 3H), 3.33 (s.3H). 110 d 8.4 (d, lH), 7.35 (m, 8H). 6.2 (d, 1H), 4.58 (t, 2H), 3.77 (s, 3H), 3.33 (s, 3H), 3.2 (t, 2H). 11 1 d 8.4 (d.lH), 7.25 (m.7H), 6.17 (d, 1H), 4.57 (t, 2H), 3.78 (s, 3H), 3.34 (s, 3H). 321 (t 2H), 2.27 (s.3H). 112 d 8.43 (d, lH), 7.41 (m, 6H), 7.19 (d_2H), 624 (m, 1H), 5.38 (s-2H), 3.76 (s, 3H), 3.33 (s, 3H). 2.36 (s.3H). 113 d 8.43 (d, lH), 7.35 (m, 3H), 7.2 (m, 3H), 7.09 (m, IH), 6.21 (d, lH), 5.37 (AB q_2H), 3.76 (s, 3H), 3.33 (s, 3H), 2.35 (s, 3H), 2.27 (s, 3H). 114 d 8.42 (s, lH). 7.4 (m, 5H). 7.19 (m.lH). 6.89 (d.lH). 6.27 (s, 1H), 4.76 (t, 2H), 4.34 (t, 2H), 3.79 (s, 3H), 3.34 (s, 3H). 115 d 8.42 (d.lH), 7.38 (m, 4H) .7.17 (ra.lH), 6.89 (d, lH), 6.24 (s.1H), 4.75 (t, 2H), 4.33 (t, 2H) , 3.79 (s.3H), 3.34 (s, 3H), 2.27 (s, 3H). 116 d 8.43 (s, lH) .7.87 (m, 3H) .7.41 (m, 4H), 6.34 (AB q, 2H), 3.78 (s, 3H), 3.33 (s, 3H). 118 d 8.41 (S.1H), 7.4 (m, 8H) .619 (s, 1H), 4.58 (t, 2H), 3.77 (s, 3H), 3.33 (s, 3H), 3.13 (t, 2H) . 119 d 8.4 (s, lH), 7.44 (m.5H), 7.2 (d, lH) .7.09 (d, lH) .6.17 (s, 1H), 4.57 (t, 2H), 3.77 (s, 3H) , 3.33 (s, 3H), 3.13 (t, 2H), 2.27 S.3H). 120 d 8.42 (d, lH), 8.14 (m.lH), 7.85 (d, lH), 7.77. (tn, lH), 7.47 (m, 6H), 7.32 (m_2H) .6.2 (d, 1H), 4.68 (m_2H), 3.76 (s, 3H), 3.54 (t_2H), 3.33 (s, 3H). 121 d 8.42 (d, lH), 8.15 (d, lH), 7.85 (d, lH), 7.75, (m.lH), 7.48 (m, 2H), 7.38 (m, 3H), 7.22 (m.lH ), 7.09 (d.lH), 6.18 (s, 1H), 4.68 (m_2H), 3.77 (s, 3H), 3.54 (t, 2H), 3.33 (s, 3H), 2.27 (s, 3H). 122 d 8.7 (lH), 8.59 (m.lH), 8.44 (s, lH) .7.77, (m, lH), 7.41 (m, 5H), 6.27 (d, 1H), 5.45 (s.2H), 3.78 (s, 3H), 3.33 (s, 3H). 123 d 8.7 (s.1H), 8.59 (d, 1H), 8.43 (d, 1H), 7.77, (ni, 1H), 7.32 (m, 3H), 7.11 (m, lH), 6.24 (m, 1H) ) .5.44 (s, 2H), 3.78 (s, 3H), 3.33 (s, 3H), 2.27 (s.lH). 124 d 8.4 (d, IH), 7.4 (m, 4H), 6.27 (d, 1H), 4.52 (m_2H), 3.78 (s.3H), 3.72 (m, 2H), 3.42 (s, 3H), 3.33 (s, 3H). 125 d 8.4 (s, lH), 7.38 (t, 1H), 7.2 (d, lH), 7.1 (d, lH), 6.22 (d, 1H), 4.5 (ra_2H), 3.78 (., 3H) .3.7 (m, 2H), 3.42 (s, 3H), 3.35 (s, 3H), 2.27 (s, 3H). 126 d 8.45 (d, lH), 7.39 (m, 2H), 7.23 (m, 4H), 7.11 (d, lH), 6.22 (d, lH), 5.41 (AB q, 2H), 3.77 (s.3H) ), 3.33 (s, 3H), 2.38 (s, 3H), 2-27 (s, 3H). 127 d 8.59 (d, lH), 7.52 (m, 1H), 7.38 (m, 2H), 7.22 (m, 3H), 7.09 (m.lH), 6.68 (cUH) .4.57 (AB q, 2H), 3.75 (s, 3H), 3.32 (s, 3H), 2.04 (s_3H). to 1 H NMR data are in ppm under the tetramethylsilane field. The couplings are designated by (s) -simplete, (d) -double, (t) -triplete, (q) -quartet, (m) -multiplete, (AB q) -AB cuartete, (dd) -doste doublets, (br s) -amplitude simplete and (br m) -ample multiplet.

BIOLOGICAL EXAMPLES OF THE INVENTION The test compounds were first dissolved in acetone in an amount equal to 3% of the final volume and then suspended in a concentration of 200ppm in purified water containing 250ppm of Trem® 014 surfactant (alcohol polyhydric ethers). The result of the test suspensions are then used in the A-F tests. Roseando these 200 ppm of the test suspensions to the point of printing on the test plants is the equivalent of a proportion of 500 g / ha.

TEST A The test suspensions were sprayed to the point of being printed on the wheat plants. The following days the tree was inoculated with a spore powder of Erysife graminis f. sp. tritisi, (the causal agent of wheat mold) and incubated in a growth chamber at 20 ° C for 7 days after which the classification of the deceases are made.

TEST B The test suspensions were sprayed to the point of being printed on the wheat plants. The following days the plant was inoculated with a reconstituted Puccin spore suspension, (the causal agent of wheat leaf mold) and incubated in a saturated atmosphere at 20 ° C for 24 hours and then moved to a 20 ° growth chamber. C for 6 days after which the classification of the deceases are made.

TEST C The test suspensions were sprayed to the point of printing them in the rice plant. The following days the plant was inoculated with a spore suspension of Pyricularia oryzae, (the causal agent of wilted rice mold) and incubated in a saturated atmosphere at 27 ° C for 24 h, and then moved to a growth chamber at 30 ° C. ° C for 5 days after which the classification of the deceases are made.

TEST D The test suspensions were sprayed to the point of printing them on the tomato plant. The following days the plant was inoculated with a spore suspension of Fitofthora infestans, (the causative agent of the tomato and potato pest) and incubated in a saturated atmosphere.

° C for 24 h, and then removed to a growth chamber at 20 ° C for 5 days after which the classification of the deaths are made.

TEST E The test suspensions were sprayed to the point of printing them on the grape plant. The following days the plant was inoculated with a spore suspension of Plasmopara viticola, (the causal agent of grape mold) and incubated in a saturated atmosphere at 20 ° C for 24 h, and then removed to a growth chamber at 20 ° C. ° C for 6 days, and then incubated in a saturated atmosphere at 20 ° C for 24 h, after which the classification of the deceases are made.

TEST F The test suspensions were sprayed to the point of printing them in the plant. cucumber. The following days the plant was inoculated with a spore suspension - from Botrytis sinerea, (the causal agent of gray mold in many crops) and incubated in a saturated atmosphere ° C for 48 h, and then removed to a growth chamber at 20 ° C for 5 days after which the classification of the deceases are made. The results of the tests A-F are given in the table A. In the table, a rating of 100 indicates a control of the mortality of 100. and a rating of 0 indicates that there is no control of mortality (relative to controls). A check mark (-) indicates that there are no test results. ND indicates that the control of the mortality has not been determined due to phytotoxicity.

Table A CmDd No. Test A Test B Test C Test D Test E Test F 1 75 85 0 0 0 »0 2 21b 37b Ob - 7b - 3 0 0 0 21 5b 68 4 0 24 0 21 5 68 0 85 0 21 16b 44 6 60 24 0 21 7 4 7 0 0 0 0 - 26 8 0 0 0 0 - 32 9 99 100 74 96 94a 0 85 85 32 22 28 to 39 11 94 99 0 92 67a 39 12 62 27 0 31 23 to 64 13 92 97 91 31 28 to 38 14 0 0 0 53 - 0 86 85 0 3 - 0 16 99 100 91 93 92a 0 17 100 100 91 64 72a 0 18 89 94 0 84 46th 7 19 0 0 0 0 I2 0 100 100 53 96 87a 46 21 99 99 90 100 94a 97 22 99 100 78. 100 100 * 87 23 99 100 96 100 78a 77 24 99 97 78 92 51a 0 99 100 90 100 80 96 26 99 100 78 61 100th 60 27 97 100 60 61 88 to 31 28 98 100 90 75 71 a 31 29 89 100 74 47 15a 0 99 100 86 96 72a 0 31 99 100 86 59 75th 1 32 32 84a 38b 84 * 93a - 33 98 100 94 92 75a 43 34 75 100 86 96 100a 81 99 100 99 92 96th 1 36 100 100 94 96 100th 81 37 99 99 94 84 95th 43 38 100 100 74 59 55th 1 39 99 99 97 83b 100a 0 40 99 100 74 99 67a 43 41 98 100 78 61 99th 77 42 63 85 0 82 47th 77 43 0 67 0 54 10a 0 44 99d 99d 78d ND 12a 87d 45 77 100 73 ND 100th 0 46 100 99 85 94b 100a 0 47 38 26 28 32 16th 48 97 99 97 91 100th 31 49 6! 68 0 83. 0 50 99 100 93 100 45a 0 51 100 100 73 99 35 to 55 52 95 85 51 73 11a 22 53 100 100 85 84 100th 22 54 99 100 97 ND 100th 0 55 73 99 53 65 100th 0 56 99 100 94 ND 100th 0 57 96 100 53 0 100th 0 58 100 100 94 - 100th 0 59 90 100 97 79 42a 0 60 98 100 99 89 77a 42 61 26 85 0 79 55th 42 62 0 99 32 79 12th 0 63 98 100 32 ND 99a 0 64 0 0 0 22. 0 65 28 68 0 0 0a 0 66 99 100 86 0 85a 0 67 100 100 91 24. 27 to 55 68 88 100 53 86 59 to 69 69 62 0 0 0. 0 70 91 99 32 74 43a 82 71 60 99 53 17 73a 0 72 91 93 32 0 - 0 73 57 94 0 23 38a 0 74 100 100 53 - 72a 0 75 99 99 94. 61a 0 76 20a 97d 0d 0 0a 0 * 1 77 21a 99 6 0 82a 0 78 IIa 86 35 0 19a 0 79 30th 97 91 0 0a 0 80 0a 97 64 0 6a 0 81 30 97 0 0 - 0 82 99 100 74 62. 0 83 0 66 0 0 6a 0 84 94 99 86 58e 93a 0 85 83 93 32 0 71a 0 86 96 100 74 100f 100a 0 87 94 100 74 15 100th 0 88 96 99 86 100f 100a 0 89 98 97 53 100f 18a 0 90 97 100 32 3 e - 0 91 58 99 0 100e 12a 0 92 31 100 53 928 96th 0 93 85 100 32 73e 87a 0 94 92a 98a 0a - 99a - 95 99 100 97 85 * 100a 0 101 98 97 86 74 - 91 102 86 67 53 57 - 91 103 100 100 86 85 - 0 104 100 100 74 100f 96a 0 105 100 100 74 100f 100th 0 106 100 too 74 100f 97a 0 107 100 100 73 100f 3a 0 108 97 97 74 82e 97a 0 109 92 99 53 90 64a 49 110 86 97 53 2 22a 11 111 97 99 86 90 52a 49 112 99 99 52 62 50a 0 113 100 100 94 45 100th 0 114 100 100 99 75 11a 0 1 Q - 115 99 100 99 99 79th 0 116 98 100 94 94 64a 0 117 98 100 86 94 84th 20 118 83 100 86 51 50a 0 119 83 100 94 90 86a 0 120 90 100 53 68 76a 0 121 99 99 97 100e 99a 0 122 78 94 0 19 11a 0 123 87 97 0 61 4a 0 124 78 86 0 0 2a 0 125 95 99 0 19 4a 0 126 100 100 97 100f 84a 0 127 97 97 97 - 47a 94 a The compound was tested with 10 pp (equivalent to 25 g / ha) "The compound was tested with 2 ppm (equivalent to 5 g / ha) c The compound was tested with 2 ppm (equivalent to 5 g / ha) d The compound was tested with 100 ppm (equivalent to 250 g / ha) and .20 »burns in plants f 100% burns in plants 8 50% burns in plants - - TEST G Southern corn rootworm The test units, each consisting of 230-mL (8-ounce) a plastic cup containing a plug of 6.5-cm2 (1 in2) and a wheat germ diet.

The solutions of each of the test compounds in 75:25 distilled acetone and water were sprayed into the cup and tray. Spraying was performed by passing the cup and the tray on a conveyor belt under a hydraulic nozzle which discharges in the form of a spray in a proportion of 0.138 kilograms of active ingredient per hectare (about 0.13 lb / acre) to 207 Kpa ( 30 psi). After the spray, the layers were dried, five seconds of incrustation of the larvae of the rootworm of the southern corn (Diabrotica undeci punctata howardi) were placed inside the crown. The cups were retained at 27 ° C and 50% relative humidity for 48 hrs, after which mortality times were recorded. The same units were recorded again for 6-8 days due to delayed toxicity. Of the test compounds the following given control of the efficiency levels of 80% or more: 44, 50, 54, 55, 56, 115 and 126.

- - TEST H Contact test against the black bean aphid The individual leaves of the mastuerzo were infested with 10 to 15 aphids (all in the morpho and growth stage of the faba aphid) and rubbed on their lining on the bottom sides as described in test G. The leaves were then colored in a bottle with a diameter of 0.94 cm (3/8 in) which contains 4 ml of a sugar solution (approximately 1.4 grams per liter) and covered with a transparent plastic cup 29 mL (1-ounce) to prevent any escape of leaf aphids. The test units were retained at 27 ° C and 50% relative humidity for 48 h, after which the mortality time was recorded. Of the test compounds, the following mortality levels were given 80% or more: 5.

TEST I Spider tick two spots Pieces of snap bean leaf, about 6.5 cm2 (lplg2) in area, that have been infected from the bottom sides with 25-30 adult spiders (Tetranichus urticae) were rubbed into their coatings on the sides of down in a hydra-rounded brush with a 75:25 solution of distilled acetone and water. The rubbing was done by passing the leaves, on a conveyor belt under a hydraulic nozzle which discharges in the form of spray in a proportion of 0.133 Kg of active ingredient per hectare (about 0.13 lb / hactarea) to 207 Kpa (30 Psi). The square sheets were placed below the sides in a square of wet cotton in a Petri dish and the perimeter of the square sheet was imprisoned on the cotton with a forcep so that the spiders could not escape above the surface of the sheet. treated. The test units were retained at 27 ° C and 50% relative humidity, for 48 h, after which the mortality times were recorded. Of the test compounds, the following mortality levels were 80% or more: 12, 13, 45, 54, 86, 88, 89, 90, 111, 113, 114, 115, 116, 11 ^, 118 , 119 and 126. The same units were retained for an additional 5 days and larvicidal / ovicidal mortality and / or development effects were recorded. The following activity levels of 80% or more were given for the test compounds: 63.

TEST J Contact activity against the green leafhopper Nymphs.

Three rice plants (Ori za sa ti va) in a leaf state of 1.5 and about 10 cm high were transplanted in a 14 mL (1/2 oz) plastic cup containing Kumisi Café artificial soil. 7 L of distilled water was then added to the cup. The test chemical was prepared by first dissolving the chemical in acetone and then adding water to produce a final test concentration of 75:25 (acetone-water). Four plastic cups, each serving as a replica, are placed in a spray chamber with a rotating platform. The layers were rubbed for 45 seconds with 50 mL of the chemical solution at a pressure of 2.0 Kg / cm2 with air atomizing nozzles. The turntable completed 7.5 rotations during 45 second spray intervals. After the chemical application, the treated layers were retained in an attached opening for drying about 2 h. After drying, the cups were placed inside conical shaped test units and the surface of the ground covered with 2 to 3 mm of quartz sand. From 8 to 10 hymphs of chrysalis 3 ° of the green grasshopper (Nephotettix cincticeps) were transferred in test units using a vacuum cleaner. The test units were retained at 27% and 65% relative humidity. Taking into account the number of dead and alive hymphs were taken 24 and 48 hours after the infestation. Insects that could not walk were classified as dead. Of the test compounds, the following mortality levels of 80% or more were given in 48 hours in an application equivalent to 0.05 Kg / hectare: 12 and 54.

TEST K Spider tick two larval spots (tetranychus urticae) The solutions of the test compounds were prepared by dissolving a minimum of acetone and then adding water containing a wet agent until the concentration of the compound was 50 ppm. The two-week-old beans were infested with spider tick eggs. Two spots were sprayed to come off (equivalent to 28 g / ha) with a test solution using a rotating platform sprayer. The plants were retained in a chamber at 25 ° C and 50 ° W of relative humidity. Of the test compounds, the following larvicidal / ovicidal activity of 80% or more was given 7 days after spraying: 54 and 84.

Claims

1. A compound selected from Formula 1, N-oxides and agriculturally suitable salts. characterized in that: -E is selected from: i) 1, 2-f-methylene optionally substituted with one of R3, R4 or both R3 or 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 RJ, R4 or both R3 and R4; and iii) a ring system selected from a monocyclic having 5 to 12 members and aromatic bicyclic fused heterocyclic ring systems, each heterocyclic ring system containing from 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen and sulfur, provided each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfides, each fused bicyclic ring system optionally contains a non-aromatic ring which optionally contains one or two Q as ring members and optionally includes one or two ring members independently selected from C (= 0) and S (0) as long as 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 members of an adjacent ring, each system of heterocyclic aromatic rings are optionally substituted with one of R3, R4 or both R 'and R "; G is C or N; 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 CR'4 and the floating double bond is attached to A; that; S; NH; N (C 1 -C alkyl); c NO (alkyl C_-C; X is OR1; S (0) m R1; O halogen; R1 is alkyl Ci-Ct, haloalkyl C.-C, alkenyl C¿-C3 haloalkenyl C2-Cβ; alkynyl C_- Cr, C 1 -C 6 haloalkynyl C 3 -C 6 cycloalkyl, C 1 -C 4 alkylcarbonyl, or C 2 -C 4 alkoxycarbonyl, R 2 is H, is C 1 -C 8 alkyl, haloalkyl CC, C 2 -C 6 alkenyl, C 2 -C 4 haloalkenyl, C 1 -C 8 alkynyl , haloalkynyl C 1 -C 6 C 3 -C 6 cycloalkyl; C 1 -C 4 alkylcarbonyl; alkoxycarbonyl C2-C; hydroxy; C-C alkoxy, or acetyloxy; R3 and R4 can independently be halogen; cyano; nitro; hydroxy; alkyl C: -C "; haloalkyl C -_- C «; C2-C6 alkenyl, "C2-C6-haloalkenyl, C-C9 alkynyl", C2-C2-haloalkynyl, Ci-C2 alkoxy, haloalkoxy C.-C ", C2-C6 alkenyloxy, alkynyloxy alkylthio C -C, alkylsulfinyl Ci -Cβ, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, NHC (O), alkyl (C 4 -C) NHC (0), (alkyl dC 4) 2NC (0); Si (R,; Ge (RÁ_.; A ") Si-C = C-; or phenyl, phenylethyl, benzoyl or phenylsulfonyl, each substitution with R8 and optionally substituted with 1 or more R10, or when E is 1,2-phenol and R3 and R4 are bonded to adjacent atoms, R * and R "* can be taken together as C-Cs alkylene, haloalkylene C, -C ^, C3-C5 alkenylene or haloalkenylene C.- C- each optionally substituted with 1-2 alkyl C.-C; R5 is H; is alkyl C.-C; haloaicyl C_-Cf, alkenyl C¿-Cs haloalkenyl C_ Cfo; alkynyl C-C; haloalkynyl C2-Cs C3-Cs cycloalkyl, C4-C4 alkylcarbonyl or alkoxycarbonyl C2-C4; And it's -0-; -S (0) n-; -NR1"'-; -C (= 0) -; -CH (0R1) -; -CHR6-; - CHR6CHR6 -; - CR6 = CR &-; -C = C-; -CHR 0-; -OCHR15-;; -CHR15S (O) n-; -S (0) nCHR15 -; - CHR150-N = C (R'7); - (R ~ 'C = N-0CH (R1"5) -; -C (R7) = N-0-; -0 -NC (R7) -; - CHR15OC (= 0) N (R? R) -; -CHRAc (= S) N (R15) -; - -CHR15OC (= 0) 0-; -CHR15OC (= S) 0-; -CHRAc (= 0) S-; -CHR15OC (= S) S-; -CHR15SC (= 0) N (R15) -; -CHR: cSC (= S) N (R: = <) -; -CHR: "SC (= 0) 0-; - CHR15SC (= S) 0 -; - CHR15SC (= 0) S; -CHRAc (= S) S -; - CHRlc, SC (= NR15) S-; - CHR15N (R15) C (= 0) N (R15) -; -CHR "ON (R1") C (= 0) N (R1.5) -; CHR150-N (R15) C (= S) N (RA -; -CHR ""? - N = C (R ") NR1 -; - CHR150 - N = C (R7) OCH2 -; - CHR150-N = C (R ~) -N = N-; -CHR150-N = C (R) -C (= 0) -; -CHR150-N = C (R7) -C (= NA "-Z :) -A1-; -CHR: ON = C (R7) -C (R7) = N-A2- A3-; -CHR150-N = C (-C (R ") = NA" -Z-; -; CHRA-N = CA) -CH20-; CHR150-N = C (R7) -CH2S-; -0-CH_CH_0-N = C (R_) -; -CHR1A C (R15) = C (R7) -; -CHR150-C (R ") = N-; -CHR: "'S-C (R ~) = N-; -C (R7) = N-NR15-; -CH = N-N = C (R7) -; -CHRA (R: r) -N = C (R ~) -; -CHR ^ N (COCH3) -N = C (R7) -; -OC (= S) NR15C (= 0) -; CHR '-C (= W :) -A1-; -CHR6CHR6-C (= W1) -A1-; CR6 = CR6-C (= W1) -A1-; -C = C-C (= WX) -A1-; -N = CR5-C (= 1) -A1-; or a direct link; and the directionality of the link Y is defined in such a way that the radical labeled on the left side of the link is linked to E and the radical on the right side of the link is linked to Z; Z1 is H or -A-Z2; W1 is 0 or S; A1 is 0; S; NR15; or a direct link; A2 is 0; NR15 or a direct link; A3 is -C (= 0) -; -S (0), -; or a direct link; Z2 is selected from: i) Ci-Cio alkyl; C_-C alkenyl; and C_-C10 alkynyl, each optionally substituted with one or more R10; ii) C3-C-cycloalkyl, C-C ^ cycloalkenyl, and phenyl, each optionally substituted with one or more Rl0; iii) a selected ring system consisting of systems of 3 to 14 monocyclic, fused bicyclic and non-aromatic tricyclic heterocyclic fused rings and systems of 5 to 14 monocyclic, fused bicyclic members and fused aromatic tricyclic heterocyclic rings, each ring system Heterocyclic contains from 1 to 6 heteroatoms independently selected from the group of 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 sulfides, each ring system aromatic and non-aromatic heterocyclics are optionally substituted with 1 or more R10; iv) a system of selected multicyclic rings consisting of systems of 8 to 14 bicyclic-fused members and tricyclic-fused rings which are a carbocyclic aromatic ring system, a non-aromatic carbocyclic ring system, or a ring system containing one or two non-aromatic rings which 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 ring remaining as aromatic carbocyclic rings, each multi-cyclic ring system optionally substituted with 1 or more R:; and v) adamantyl optionally substituted with one or more Ri0; each R6 is independently H; 1-2 CH <; C2-C3 alkyl; C 1 -C-alkoxy; cycloalkyl C < -C "; formylamino; alkylcarbonylamino C "-C4; akoxycarbonylamino C2-C4; NH2C (0) NH; (Ci-C alkyl,) NHC (O) NH; (alkyl C: -C.). NC (0) NH; N (C 1 -C 3 alkyl) 2; piperinidyl; morpholinyl; 1-2 halogen; cyano; or nitro; each R7 is independently H; alkyl C; -C; haloalkyl C? -C6; Ci-Cb alkoxy; haloalkoxy? DC"; alkylthio C? -C6; alkylsulfinyl C? -C <; alkylsulfonyl Ci-Ct-; haloalkylthio Ci-Cd; haloalkylsulfinyl C.-C,; haloalkylsulfonyl Ci-Cb; C2-C alkenyl "; haloalkenyl C_-C "; C-C6 alkynyl; haloalkynyl C ^ -C ^; C -C "cycloalkyl; C 4 -C 4 alkylcarbonyl; C 1 - alkoxycarbonyl; halogen; cyano; nitro; hydroxy; Not me; NH (alkyl C? ~ Cb); N (alkyl C.-C,); or morpholinyl; Z is selected from: i) C3-Cß cycloalkyl; Cycloaiqueml C.-C- and '£ < = n? l, each one substituted with R9 and optionally substituted with 1 or more R10; ii) a ring system selected from systems consisting of 3 to 14 monocyclic, fused bicyclic, and fused non-aromatic tricyclic heterocyclic ring members and systems consisting of 5 to 14 fused bicyclic monocyclic members and fused aromatic tricyclic heterocyclic rings, each Heterocyclic ring system contains from 1 to 6 heteroatoms independently selected from the group of 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 sulfides, each system of aromatic and non-aromatic heterocyclic rings substituted with R9 and optionally substituted with 1 or more R "; iii) a system of multi-cyclic rings selected from systems of 8 to 14 bicyclic-fused members and tricyclic-fused rings, which are a system of carbocyclic aromatic rings, a system of non-aromatic carbocyclic rings, or a system of rings containing one or two non-aromatic rings which include one or two Q as ring members and one or two ring members independently selected from C (= 0) and S (0), and any ring remaining as aromatic carbocyclic rings, each ring system multicyclic substituted ccn R 'and optionally substituted with one or more R ~; iv) adamantyl substituted with R 3 and optionally substituted with one or more R "; - every Q is independently selected from -CHR13-, NR13 -, - 0- and -S (0) p-; R8 is H; 1-2 halogen; alkyl C: -C "; haloalkyl C! -C6; C6-C6 alkoxy; haloalkoxy C: -C; C2-C6 alkenyl; C2-C6 haloalkenyl; C 1 -C 2 alkynyl; C? ~ C6 alkyl; haloalkitium C? -C6; alkylsulfinyl C.-C ,,, alkylsulfonyl C? -C6; C ciclo-Cf cycloalkyl; alkenyloxy Cj-Cß, 'CO (alkyl Cj.- C6); N (C 1 -C 4 alkyl); cyano; nitro; SiR19R20R21; or GeR19R20R21; R 9 is C 1 -C 4 alkyl, substituted with 2-3 C 1 -C 3 alkoxy; C2-C4 alkynyl substituted with a hydroxy or 1-3 C1-C4 alkoxy; C2-C6 haloalkynyl; C-C ^ cycloalkyl substituted with a select member of 1-4 halogen, 1-2 C 1 -C 3 alkyl, 1-2 C 1 -C alkoxy and a Z 3; cicloalquer.il C.-C, -. or cycloalkoxy C-C? each optionally substituted with a select member of 1-2 halogen, 1-2 Ci-C alkyl, 1-2 Ci-C3 alkoxy and a Z3; adamantyl; C.sub.1 -C.alkoxyalkyl; C2-C6 alkylthioalkyl; cyanoalkyl C_-C "; alkoxyalkynyl C-Cd; tetrahydropyranyloxyalkynyl C-C:; C1-C3 alkoxy substituted with cyano; , C; = 0) Rh or C (= 0) N (R26) 2; C3-C6 haloalkenyloxy, -alkynyloxy C < -C; C3-C6 haloalkynyloxy; C ^ -C "alkoxyalkoxy; trialkylsilylalkoxyalkoxy C5-Cg; C ^ -C, alkythoxy alkoxy; Ci-C alkylthio, substituted with cyano, C (= 0) OR26 or C (= 0) N (R " '); haloalkylsulfinyl C 6 alkyl; haloalkylsulfonyl C:.? -C,; C3-C6 alkenylthio,' C3 haloalkenylthio -Cb; alkynylthio C < -C "; haloalkynylthio C3-C6; alkoxyalkylthio C_-C.; C2-C6 alkylthioalkylthio; thiocyanate; hydroxy; mercapto; Not me; N (R26) (R28); SiR22R23R24; GeR-R-'R--; (RÁ? Si-C = C-; OSi (R25) 3; OGe (R25) 3; C (= 0) RQ; C (= S) R ""; C (= 0) OR "; C (= S) ) OR26; C (= 0) SR26; C (= S) SRA C (= 0) N (R ß) _; C (= S = N (R26) 2; C (= NR26) 0R27; 0C (= 0) R26; 0C (= S;?; SC (= 0) RA C (= S) R26; N (R26) C = 0) R26; N (R26) C (= S) R 0C (= 0) 0RA OC (= 0) S R27; S (0) 2N (R26); OS or N (R ") S, 0) _R-7 or R 'is benzyloxy, benzyloxymethyl, phenylethynyl, phenoxymethyl, phenylthio, phenylsulfonyl, benziniltio, pyridinylmethyl, piridinilmetiloxi, piridiniloximetil, pyridinylethynyl, pyridinylthio, thienylmethyl, thienylthio, furanylmethyl, furanyloxy, furanylthio, pirimidiiilmetil or piminidiltio, each optionally substituted on the aromatic ring with one of R11, RO both R " 'and R" ~; or R' is alkyl or C2-C6 alkoxy substituted with 1-2 phenyl, naphthalenyl, phenoxy, benzyloxy, pyridinyl, pyrimidinyl, thienyl, furanyl or each aromatic ring optionally substituted with one of R11, R12, or both R ' "and R"; or RJ is -A4-Z4; each R10 is independently halogen, C1-C4 alkoxy optionally substituted with 1-3 Ci-C ,; ~ C4 haloalkyl C;? C2-C6 haloalkenyl C-C "; C2-CTI; Cj-Cs haloalkinil; C -C cycloalkyl; C2-C6 alkoxyalkyl; - -alkylthioalkyl C¿-C0; cyanoalkyl C "-C, -; alkoxyalkynyl C3-C6; tetrahydropyranyloxyalkynyl C-Ci,; benzyloxymethyl; C4-C4 alkoxy; haloalkoxy C -C_; C3-Cfe alkenyloxy; C3-C0 haloalkenyloxy; Alkynyloxy C.-C; C3-C6 haloalkynyloxy; cycloalkoxy C.-C,; C2-Ce alkoxyalkoxy; trialkylsilylalkoxyalkoxy C-C; C2-C6 alkylthioalkoxy; C 1 -C 4 alkylthio; haloalkitium C -C_; C 1 -C 4 alkylsulfinyl; haloalkylsulfinyl C? -C; C 1 -C 4 alkylsulfonyl; haloalkylsulfonyl C.-C.,; C3-C6 alkenylthio; C3-Cb haloalkenithium; Alkylthio C-C "; C3-C6 haloalkenylthio; alkoxyalkylthio C.-C.,; C2-C6 aylthioalkylthio; nitro; cyano; thiocyanate; Hydroxy; mercapto; N (R "°) ^; SF5; Si (R2A; Ge (R2A; (RA-IF-C = C-; OSi (R-).; 0Ge (R-5 • C (R18) = NOR17; C (= 0) R- "; C (= S) P; C (= 0> OR-r; C (= S) ORb; C (= 0) SR26; C (= S) SR- *; C (= 0) N (R- '?; OC (= S) N (R-) _; C (= N Rfe) 0 R27; OC (= 0) R2 < 5; OC (= S) R ~; SC (= 0) R- '; SC (= S) R26; N (R6) C (= 0) R26; N (Rh) C (= S) R-; OC (= 0) OR 0C (= 0) SR27; OC (= 0) N (R26) 2; SC (= 0) 0RA SC (= 0) SR "1; S (O) ^ 0 R26; S (0) 2N (R26) 2: 0S (0) _ R NÍR-'JSIO) R or phenyl, benzyl or phenoxy, each optionally substituted on the phenyl ring with one of RR "", or both R'1 and R * ~; or When Y and a R10 are attached to adjacent atoms in Z and Y is -CHR150-N = C (R7) -, -0-N = C (R) -, -0-CH ^ CH.ON = C (R7) -, CHR150-C (R15) = C (R7) -, -CH = NN = C (R) -, -CHRA (RA -N = C (R7) - OR -CHR 15N (COCH3) -N = C (R7) -, R ~ and the adjacent -forementioned union R10 can be taken simultaneously as - (CH2) r-J- similarly J is linked to Z; J is -CH-; -CH.CH.-; -OCH_-; -CH_0-; -SCH_-; -CH2S-; N (R16) CH2_; or -CH2N (R:) -; each group CH_ of J mentioned above is optionally substituted with 1 to 2 CH3; Z3 is phenyl, naphthalenyl, l-pyrrolyl, furanyl, thienyl, l-pyrazolyl, l-imidazolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, 1H-1, 2, 3-triazolyl, 2H-1,2,3-triazolyl, ÍH-I, 2,4-triazolyl, H-1,2,4-triazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1, 2, 5-oxadiazolyl, 1,3,4- oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolii, l, -tetrazolyl, 2H-tetrazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1, 3, 5-triazinyl, 1, 1,4-triazinyl, or 1,2,4,5-tetrazinyl, each optionally substituted with one of R11, R12, or both R11 and R1-; A4 is O; S; open chain or C1-C0 alkylene branch; Or a direct link; Z4 is selected from: i) lJ-pyrrolyl, l-pyrazolyl, IH-imidazolyl, isozazolyl, oxazolyl, isothiazolyl, thiazole, 1H-1,2,3-triazolyl, 2H-1,2,3-triazolyl, 1H- 1, 2, 4-triazyl, 4H-1,2,4-triazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1, 2, 5-oxadiazolyl, 1,3,4-oxadiazolyl , 1, 2, 3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 2, 5-thiadiazolyl, 1, 3, 4-thiadia-olyl, 1-tetrazolyl, 2H- -tetrazolyl, pyridazinyl, pyrazinyl, 1, 3, 5-triazinyl, 1, 2, 4-triazinyl, and 1, 2, 4, 5-tetrazinyl, each optionally substituted with one of R11, R ", or both R11 and R12; ii) a ring system selected from a 3-way system 14 monocyclic, fused bicyclic, and fused non-aromatic tricyclic heterocyclic rings and systems of 8 to 14 bicyclic-fused members and fused aromatic tricyclic heterocyclic rings, each heterocyclic ring system contains from 1 to 6 heteroatoms independently selected from the nitrogen, oxygen group and sulfur, provided that each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfides, each aromatic and nonaromatic heterocyclic ring system optionally substituted with one of R "~ O both R11 and R12; and iii) a system of multicyclic rings selected from a system of 8 to 14 bicyclic-fused members and tricyclic-fused rings which are a carbocyclic aromatic ring system, a non-aromatic carbocyclic ring system, or a ring system that contain one or two non-aromatic rings which include one or two Q as ring members and one - or two ring members independently selected from C (= 0) and S (O) ¿, and any remaining ring as aromatic carbocyclic rings , each multicyclic ring system optionally substituted with one of R11, R12, or both R11 and R12; each R11 and each R12 is independently 1-2 halogen; alkyl C? ~ C; haloalkyl C.-C ,; C2-C6 alkenyl; C2-Cb haloalkenyl; C 1 -C alkynyl "; haloalkinyl C2-Cß; C-C6 alkoxyalkyl; C2-C2 alkylthioalkyl; C3-C6 alkoxyalkynyl; tetrahydropyranyloxyalkynyl C-Ci,; benzyloxymethyl; C? -C alkoxy; haloalkoxy C.-C4; C3-C6 alkenyloxy; haloalkenyloxy C-C "; C 1 -Ce alkynyloxy; haloalkynyloxy C3-C6; alkoxyalkoxy C.-C ,,, C5-C9 trialkylsilylalkoxyalkoxy; C2-C2 alkylthioalkoxy; alkylthio C.-C; haloalkitium C? ~ C4; alkylsulfinyl C_-C_; haloalkylsulfinyl C? ~ C4; C 1 -C 4 alkylsulfonyl; haioalkylsulfonyl C? ~ C4; alkenylthio C.-C- ,; C3-C6 haloalkenylthio, "C-C0-alkylthioalkylthio; nitro; cyano; thiocyanate; hydroxy; mercapto; N (R - '") _; SF-; Si (R "=), Ge (R25) 3; (R25) 3Si-C = C-; OSi (R2A; OGe (Rr) _; C (= 0) R" '; C (= S) R26; C (= 0) OR26; C (= S) OR26; C (= 0) SR; C (= S) SR- ~; C (-0) N (R26) 2; C (= S) N (R26) 2; 0C (= 0) R2h; 0C (= S1R- '; SC (= 0) R- "; SC (= S) R26; N (R26) C (= 0) R26; N (R6) C (= S) R-; OC (= 0) PRA OC (= 0) SR27; OC (= 0) N (R6) 2; SC (= 0) 0RA SC (= 0) SRA S (0) 2OR26; S (0) 2N (R26) 2: 0S (0) 2 R27; N (R "") S (0). R27; Or phenyl, phenoxy, -benzyl, benzylsilyl, phenylsulfonyl, phenylethynyl, or pyridinylethynyl, each optionally substituted on the aromatic ring with 1-2 independently selected halogen groups, C: -C4 alkyl, C1-C4 haloalkyl, C1-6 alkoxy C4, haloalkoxy Ci-C, nitro and cyano; each R13 is independently H; alkyl C_-C "; haloalkyl Ci-C? * Or phenyl optionally substituted with halogen, C1-C alkyl, C-C haloalkyl, C: ~ C alkoxy; haloalkoxy C1-C4, nitro or cyano; R14 is H; halogen; alkyl C: _C.; haloalkyl C; _C; C6-C6 alkenyl; haloalkenyl C_-C "; C_X alkynyl "; haloalkynyl C2_Cs; or cycloalkyl Cj_C; Each R15 is independently H; alkyl C.-C; C-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano; When Y is -CHR1N = C (= 0) N (R: '• -, the two R1"' attached to nitrogen atoms of the aforementioned group can be taken simultaneously as - (CH) .-; or when Y is -CHR150-N = CA) NR1"-, R7 and adjacently the junction R15 can be taken simultaneously as -CH2- (CH2) a-; -0- (CH) s-; -S- (CH) ..; O-N (C1-C3 alkyl) - (CH1) S ~; with the directionality of the aforementioned bond defined such that the radical labeled on the left-side of the bond is bonded to the carbon and the radical on the right side of the bond is bonded to the nitrogen; R16, R17 and R18 are each independently H; alkyl C? _ C3; C3-Cfe cycloalkyl; or phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 0 haloalkyl, C 1 -C 4 alkoxy, C 1 -C haloalkoxy, nitro or cyano; R19, R20, R21, R2? , and R ~ * 'are each independently alkyl C? _C6, haloalkyl C? -C "; C__C alkenyl "; C? -C alkoxy; or phenyl; R24 is haloalkyl CL_C4; Each R25 is independently alkyl C._C_; haloalkyl C? _ C4; C2-C4 alkenyl; C -C alkoxy; or phenyl; Each R26 is independently H; alkyl C.-C; Ci-Cß haloalkyl; alkenyl C¿_C;; haloalkenyl C_-C.,; C 1 -C 6 alkynyl, "haloalkynyl C 1 -Ce; cycloalkyl C, -C, or phenyl or benzyl, each optionally substituted on the phenyl ring with 1-2 groups independently selected from halogen, C 1 -C 4 alkyl / haloaicyl C1 C4, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro and cyano, each R 27 is independently C 1 C alkyl, C 1 -C 9 haloalkyl, C 1 -C 6 alkenyl, C 1 -C 6 haloalkenyl, C 2 -C 6 alkynyl, haloalkynyl C 2 -C 3 cycloalkyl C, -C "or phenyl or benzyl, each optionally substituted on the phenyl ring with 1-2 groups independently selected from -halogen, alkyl C? _C ?, haloalkyl C? _C4, alkoxy C1-C4, haloalkoxy C1-C4, nitro and cyano; each R28 is independently haloalkyl CC; DC; haloalkenyl C.-C; C-C alkynyl; haloalkynyl C-C; C-C, cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with 1-2 groups independently selected from halogen, C-C alkyl, C-C haloalkyl, C-C alkoxy, haloalkoxy C1-.C4, nitro and cyano; Each R29 is H; alkyl C-C; haloalkyl; C-C alkenyl; haloalkenyl C_-C; C-C alkynyl; haloalkynyl C-C; C_C cycloalkyl; or benzyl, optionally substituted on the phenyl ring with 1-2 groups independently selected from halogen, C3-C4 alkyl, C-C haloalkyl, C12 alkoxy, C1-C4 haloalkoxy, nitro and cyano; Each R30 is H; haloalkyl C_C; C-C alkenyl; haloalkenyl C-C; C-C alkynyl; haloalkynyl C-C; C-C cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with 1-2 groups independently selected from halogen, C1-C4 alkyl, C-C haloalkyl, C-C alkoxy, C1-C4 haloalkoxy, nitro and cyano; m, n and p are each independently 0, 1 or 2; r is 0 or 1; and - - s is 2 or 3; as Y is -CH (OR15) -, -CHR'- -CHR "CHRA -CR ° = CRA -C = C-, -CHR150-, OCHR15-, - A) C = N-OCH (R1 ') -, -CHR150- N = C (R7) -CH20-, -CHR150-C (R' ") = C (R ~) - , -CHR'-C (^ W1) -A1-, CHR6CHRβ-C (= W1) -A1-, -CR '= CR' -C (= W ") -A1- OR -C = CC (= W) x) -A1-, therefore Z can be as phenyl, furanyl thienyl, pyridinyl and pyrimidinyl. 2. A compound according to claim 1, characterized in that: E is selected from the group 1, 2-phenylene; 1,5-, 1,6-, 1,7-, 1,8-, 2,6-, 2,7-, 1,2-, and 2,3-naphthalenediyl; 1H-pyrrolo-1,2-, 2,3- and 3,4-diyl; 2,3- and 3, 4-furandil; 2,3-and 3, 4-thiofenediyl; L-pyrazolo-1, 5-, 3,4- and 4,5-diyl; 1H-imidazolo-1, 2-, 4,5- and 1,5-diyl; 3,4- and 4,5-isoxazolediil; 4, 5-oxazoled? L; 3,4- and 4,5-isothiazolediyl; 4,5-thiazolediyl; LFI-1, 2, 3-triazolo-l, 5- and 4,5-diyl; 2_T-1, 2,3-thiazolo-4, 5-diyl; 1H- 1, 2, 4-triazolo-1,5-diyl; 4H-1, 2,4-triazolo-3,4-diyl; 1, 2, 3-oxadiazolo-4,5-diyl; 1, 2, 5-oxadiazolo-3, -diyl; 1, 2, 3-thiadiazolo-4,5-diyl; 1, 2, 5-thiadiazolo-3, 4-diyl; li -tetrazolo-1, 5-diyl; 2,3- and 3, 4-pyridinediyl; 3,4- and 4,5-pyridazinediil; 4, 5-pyrimidinediyl; 2, 3-pyrazinediil; 1, 2, 3-triazino-4,5-diyl; 1, 2, 4-triazino-5,6-diyl; IH-indolo-l, 4-, 1,5- 1,6, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5 -, 3.6-, 3.7-, 1,2-, 2,3-, 4,5-, 5,6-, and 6,7-diyl; 2,4-, 2,5-, 2,6-, - -2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-, 4,5 -, 5,6- and 6,7-benzofurandiyl; benzo [b] thiophene-2, 4-, 2,5-, 2,6-, 2, 1-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3- , 4,5-, 5,6 and 6,7-diyl; 1H-indazolo-1, 4-, 1,5-, 1,6-, 1,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5 , 6- and 6,7-diyl; lyf-benzimidazole-1, 4-, 1,5-, 1,6-, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5 , 6- and 6,7-diyl; 1,2-benzisoxazolo-, 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-benzoxazolediil; 1, 2-benzisothiazolo-, 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-benzothiazolediil; 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-quinolinediil; 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-isoquinolinediil; 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-cinnolinediil; 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-quinazolinediil; 2,5-, 2,6-, 2,7-, 2,8-, 2,3-, 5,6-, 6,7-, and 7,8-quinoxalinediil; 1,8-naphthyridino-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-pteridinediil; pyrazolo [5, 1-io] thiazolo 2,6-, 2,7-, 3,6-, 3,7-, 2,3-, and 6,7-diyl; thiazolo [2, 3-c] -1, 2, 4-triazolo-2, 5-, 2,6-, 5,6-diyl; 2-oxo-l, 3-benzodioxolo-4, 5- and 5,6-diyl; 1,3-dioxo- - -lff-isoindolo-2, 4-, 2,5-, 4,5- and 5,6-diyl; 2-oxo-2if-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; [1, 2, 4] triazolo [1, 5-a] pyridine-2,5-, 2,6-, 2,7-, 2,8-, 5,6-, 6,7-, and 7, 8-diyl; 3,4-dihydro-2, 4-dioxo-2f-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-d] thiazolo-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-quinolinediil; 2, 3-dihydro-l, 1,3-trioxo-1,2-benzisothiazolo-2, 4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-diyl; 1, 3-benzodioxolo-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-4J? -cyclohepta [b] thiophene-2, 4-, 2, 5-, 2,6-, 2,7-, 2,8-, 3,4-, 3, 5-, 3, 6-, 3,7-, 3,8-, and 2,3-diyl; each aromatic ring system is optionally substituted with one of RJ, R ", or both R3 and R4, is O; R1 is alkyl CC or haloalkyl C.-C; R1 is H; alkylC ~ C; haloalkyl CC"; CC cycloalkyl; R3 and R4 are each independently halogen; cyano; nitro; alkyl C ~ C; haloalkyl C-C; C.-C alkoxy; haloalkoxy C.-C; alkylthio C -C; alkylsulfonyl C-C; alkylcarbonyl C ~ C; C 1 -C alkoxycarbonyl; (rent C-C4) NHC (0); (alkyl CC .NC (O); benzoyl; or phenylsulfonyl; Y is -0-; -S (0) n ~; -NR- "-; -C (= 0) -; -CH (OR:") -; -CH2-; -CH2CH2-; -CH = CH-; -C = C-; -CH.O-; -OCH_-; -CH¿S (0) n-; -S (0) nCH2-; -CH0-N = C (R ") -; A) C = N-OCH (R1") -; -C (R "AN-0; Ó a direct bond; R7 is H; alkyl * C ~ C; haloalkyl C, -C; alkoxy-C-alkylthio-C; alkenyl, C-; C2-C6 alkynyl; cycloalkyl CC; halogen; or cyano; or when Y and R10 are joined to adjacent atoms in Z and Y is -CH2-0-N = C (R7), R and the aforementioned adjacent linkage R10 can be taken at the same time as - (CH ..) r-J- each J is linked to Z; Z is selected from the group C -C, cycloalkyl, phenyl, naphthalenyl, anthracenyl; phenaltrenyl, li? -pyrrolyl; furanyl, thienyl, lff-pyrazolyl, 1/1-imidazonyl, isoxazolyl, oxazolyl; isothiazolyl, thiazolyl, 1H-1, 2, 3-triazolyl; 2H-1,2,3-triazolyl; 1H-1, 2,4-triazolyl; 4H-1, 2,4-triazolyl; 1, 2, 3-oxadiazolyl; 1, 2, 4-oxad? Azolyl; 1,2,5-oxadiazolyl; 1, 3, 4-oxadiazolyl; 1, 2, 3-oxadiazolyl; 1, 2, 3 thiadiazolyl; 1,2,4 thiadiazolyl; 1,2,5 thiadiazolyl; 1,3,4 thiadiazolyl; li? -tetrazolyl; 2i? - Tatrazolyl; pyridinyl; pyridazinyl; pyrimidinyl; pyrazinyl; 1, 3, 5-triazinyl; 1, 2, 4-trazinyl; 1, 2, 4, 5-tetrazinyl; líf-indolyl; benzofuranyl; benzo [b] thiophenyl; 1H-iindazolyl; lff-benzimidazolyl; benzoxazolyl; benzothiazolyl; quinolinyl; isoquinolinyl; cinnolinil; phthalazinyl; qumazolinyl; quinoxalinyl; 1,8-naphthyridinyl; pteridinyl; 2, 3-dihydro-liY-indenyl; 1, 2, 3, 4-tetrahydronaphthalenyl; 6,7,8,9-tetrahydro-5i? -benzocycloheptenyl; 5, 6, 7, 8, 9, 10-hexahydrobenzocyclooctenyl; 2, 3-dihydro-3-oxobenzofuranii; 1,3-dihydro-l-oxoisobenzofuran? L; 2, 3-dihydro-2-oxobenzofuranyl; 3, 4-dihydro-4-oxo-2'T-l-benzopyranyl; 3, 4-dihydro-l-oxo-lH-2-benzopyranyl; 3, 4-dihydro-3-oxo-liT-2-benzopyranyl; 3, 4-dihydro-2-oxo-2. £ f-l-benzopyranyl; 4-oxo-4ff-l-benzopyranyl; 2-oxo-2ff-1-benzopyranyl;

2, 3, 4, 5-tetrahydro-5-oxo-l-benzoxepinyl; 2, 3, 4, 5-tetrahydro-2-oxo-l-benzoxepinyl; 2, 3-dihydro-l, 3-dioxo-li? -isoindonyl; 1,2,3,4-tetrahydro-l, 3-dioxoisoquinolinyl; 3, 4-dihydro-2, -dioxo-2-l, 3-benzoxazinyl; 2-oxo-l, 3-benzodioxolil; 2, 3-dihydro-1,3,1-trioxo-1,2-benzisothiazolyl; 9i? -fluorenyl; azulenil; and thiazolo [2, 3-c] -1, 2,4-triazole; each group substituted with R9 and optionally substituted with one or more R ~; and R15 is H; alkyl C ~ C; or cycloalkyl C, - C ^.

- .- 3. A compound in accordance with the claim 2 characterized in that: E is selected from the group 1, 2-phenylene; 1,6-, 1,7-, 1,2-, and 2, 3-naphthalenediyl; 2,3- and 3, 4-furandil; 2,3- and 3, 4-thiofenedil; 2,3- and 3, 4-pyridinedil; 4,5-pyrimidinedil; 2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandyl; and benzo [b] thiophene-2, 4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-diyl; each aromatic ring system optionally substituted with one of R? "or both R3 and R4; Z is selected from the phenyl group; naphthalene; 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 R and optionally substituted with one or more R10; R7 is H; alkyl C-C; Halcalkyl C; -C; C-C alkoxy; alkylthio C-C; alkenyl C.-C; C2-C alkynyl; C-C cycloalkyl; halogen; or cyano; or R 9 is cycloalkyl substituted with a minor member selected from 1-2 halogen, 1-2 C 1 -C alkyl, 1-2 C 1 -C alkoxy, and a Z 3; C-C-cycloalkyl, optionally substituted with a minor member selected from 1-2 halogen, 1-2 C-C alkyl, 1-2 C-C alkoxy, and a Z3; haloalkylsulfinyl C-C,.; haloalkylsulfonyl C-C, thiocyanate; SiR2R3R24; GeR-'R RA (RA. YES-C = C-; C (= 0) R29; -C (= 0) 0R30; S (0) 2N (RA; OS (0) _R- ~, or R 'is benzyloxy, phenylethynyl, phenoxymethyl, phenylthio, phenylsulfonyl, benzinylthio, pyridinylmethyloxy, pyridinyloxymethyl, pyridinylethynyl, or furanyloxy, each optionally substituted on the aromatic ring with one of R11, R12, or both R11 and R12; or R '"is C-C alkyl or C2-C6 alkoxy substituted with 1-2 phenyl, naphthalenyl, phenoxy, benzyloxy, pyridinyl, pyrimidinyl, thienyl, or furanyl, each ring aromatic optionally substituted with one of Ri, R12, or both R11 and R12; or Rq is -A "-Z; each R10 is independently halogen; C4-C4 alkynyl C2-C6 haloalkyl; nitro; cyano; Si (RA S! (RA -Si-C = C-; or When Y and an R10 are joined to adjacent atoms in Z and Y is -CHRA-N = C (R7) -, R the aforementioned adjacent junction R10 can be taken simultaneously as - (CH1) rJ- each J is attached to Z; J is -CH2-; -CH1CH2-; Z3 is phenyl, furanyl, thienyl or pyridinyl, each optionally substituted with one of Ri, R '~, or both R11 and R12; A4 is a direct link Z4 is 1,3-benzodioxolyl optionally substituted with one of R11, R12, or both R11 and R ~; and r is 1;

4. A compound in accordance with the claim 3, characterized in that: E is selected from the group of 1,2-phenylene; 2,3- and 3,4-thiophenediyl; and 2,3- and 3, 4-p? ridinediil; each aromatic ring system optionally substituted with one of R3, R4, or both R3 and R4; A is 0 or N; X is OR1; R1 is alkyl C-C; R2 is H or C-alkyl; -C_; And it's -0-; -S (0) n-; -NR1"-; -C (= 0) -; -CH (OR:" A; -CH2-; -CH2CH-; -CH = CH-; -C = C-; -CH.O-; -OCH__; -CH¿S (0) n-; -S (0) nCH2-; -CH0-N = C (R7) -; (R) C = N-OCH (R: ") -; - CH.OC (= 0) NH - CH2S - C (R7) = N, or a direct bond: Z is selected from the phenyl, 2 - thiazolyl group; 1,2,4-thiadiazolyl, pyridinyl, and pyrimidinyl, each group substituted with R and optionally substituted with one or more R 10, R 7 is H, CC alkyl, haloalkyl CC, C-C 3 alkoxy, C 1 alkylthio or cyclopropyl; R15 is H; alkylC ~ C; or cyclopropyl;

5. A compound according to claim 4, characterized in that: R1 is methyl; R2 is methyl; - - And it's -0-; -CH20-; -CH.O-N = C (R ~) -; - (R ~) C = N-OCH (R1) -; R9 is C3-C-cycloalkyl substituted with a Z "; cycloalkoxy C-C; SiR22R23R24; GeR-R-'R-"; (RA. Si-C = C-; S (0) 2OR26; S (0) 2N (R2A, or OS (0) .R- "; or R'1 is benzyloxy, pyridinylmethyloxy, each optionally substituted on the ring aromatic with one of R?:, R ± _, or both R11 and R12; or R9 is alkyl CC "substituted with phenyl optionally substituted with one of R1 *, R" ~, or both R'- and R "; or R9 is -A4-Z4; each R10 is independently halogen, C-C4 haloalkyl alkynyl C- or Si (R ~), and Z3 is phenyl, optionally substituted with one of R ±?, R12, or both R11 and R12;

6. A compound according to claim 5, characterized in that: Y is -0-; -CH20-N = C (R ~) -; and Rq is cycloalkyl CC, substituted with a Z; cycloalkoxy; C3-C6; SiR22R3R24; GeR "R-'R"; or (R "" "'), Si-C = C-; or R9 is benzyloxy, optionally substituted on the aromatic ring with one of R", R ", or both Ri- and R" ~; or R9 is -A4-Z4; The compound according to claim 6, which is selected from the group: - -4- [2 - [[3- (1,3-benzodioxol-5-yl) -1,2,4-thiadiazole-5- il] oxy] phenyl] -2,4-dihydro-5-methoxy-2-methyl-3'-1, 2,4-thiazol-3-one; 4- [2- [[[[1- [3- [dimethyl (3,3,3-triumphloropropyl) silyl] phenyl] ethylidene] amino] oxy] methyl] phen il] -2,4-dihydro-5-m .etoxy-2-methyl-3.Hl, 2,4-thiazol-3-one; 4- [2- [3- [(2-chlorophenyl) ethoxy] phenoxy] phenyl] -2,4-dihydro-5-methoxy-2-methyl-3Hl, 2,4-thiazol-3-one; 4- [2- [[3- [1- (4-chlorophenyl) cyclopropyl] -1,2,4-thiadiazol-5-yl] oxy] phenyl] -2,4-dihydro-5-methoxy-2-methyl -3H-1, 2,4-triazol-3-one; 4- [2- [[3- [l- (4-chloropheniD cyclopropyl] -1,2,4-thiadiazol-5-yl] oxy] phenyl] -6-2,4-dihydro-5-methoxy-2- metii-4- [2- [[[[1- [3- [Tris (trifluoromethyl) germyl] phenyl] ethylidene] amino] oxy] met yl] phenyl] -3H-1, 2,4-triazol-3-one and 2,4-dihydro-5-methoxy-2-methyl-4- [2- [3- [2- (trimethylsilyl) ethynyl] phenoxy] phenyl] -3H-1,2,4-triazol-3-one 8. a fungic composition to, characterized in that it is understood that a compound according to claim 1 becomes fungicidally effective with the minimum of a surfactant, a solid diluent or a liquid diluent. 9. A method for controlling plant mortality caused by pathogens of fungal plants comprising the application to the plant or a portion thereof, or to the seed of the plant or to the plant born from seed, and that a compound in accordance with Claim 1 is fungicidally effective. 10. An arthropocidal composition comprising a compound according to claim 1 becoming arthropocidally effective with a minimum of a surfactant, a solid diluent or a liquid diluent. 11. A method that controls arthropods that comprises contacting the arthropods in their environment with a compound according to claim 1 and becomes arthropocidally effective. SUMMARY OF THE INVENTION In the present invention, the compounds of formula (I), their N-oxides and the agriculturally suitable salts are described, which are useful as fungicides and arthropodicides, where A is 0; S; N; NR5; or CR14; G is C or N; provided that when G is C, then A is 0, 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; is 0; S; NH; N (C-C6 alkyl); or N0 (C-C alkyl); X is OR1; SÍOJmR1; or halogen; R1 is C-C6 alkyl; haloalkyl C.-C; C2-C6 alkenyl; C6-C6 haloalkenyl; C2-C6 alkynyl; haloalkynyl C-C; C-C cycloalkyl; C2-C4 alkylcarbonyl; or C2-C alkoxycarbonyl; R2 is H; alkyl C-C; C6-C6 haloalkyl; C2-C3 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C-C6 cycloalkyl, * C-C4 alkylcarbonyl; C2-C4 alkoxycarbonyl; hydroxy; C-C2 alkoxy; or acetyloxy; m is 0, 1 or 2; and E, R5, Y, Z and R14 are as defined in the description. It also describes the compositions containing the compounds of formula (I) and a method for controlling plant mortality caused by fungal plant pathogens that involves the application of an effective amount of a compound of formula (I). It also describes the compositions containing the compounds of Formula (I) and a method for controlling arthropods which involves contacting the arthropods or their environment with an effective amount of a compound of formula (I).