MX2009002012A - Fungicides. - Google Patents

Fungicides.

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Publication number
MX2009002012A
MX2009002012A MX2009002012A MX2009002012A MX2009002012A MX 2009002012 A MX2009002012 A MX 2009002012A MX 2009002012 A MX2009002012 A MX 2009002012A MX 2009002012 A MX2009002012 A MX 2009002012A MX 2009002012 A MX2009002012 A MX 2009002012A
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MX
Mexico
Prior art keywords
optionally substituted
alkyl
hydrogen
compounds
methyl
Prior art date
Application number
MX2009002012A
Other languages
Spanish (es)
Inventor
Hans-Georg Brunner
Fredrik Cederbaum
Fiona Murphy Kessabi
Laura Quaranta
Renaud Beaudegnies
Original Assignee
Syngenta Participations Ag
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Publication date
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Publication of MX2009002012A publication Critical patent/MX2009002012A/en

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Quinoline Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compounds of the general formula wherein the substituents are as defined in claim (1), are useful as fungicides.

Description

FUNGICIDES Description of the Invention This invention relates to new quinolinyl oxyalkanoic acid amides, processes for preparing them, compositions containing them and their methods of use for combating fungi, especially plant infections caused by fungi. Certain derivatives of quinolinyloxyalkanoic acid amides and their use as bactericides in agriculture and horticulture are disclosed, for example, in WO 04/047538 and JP 2001-89453. The present invention relates to the provision of particular substituted quinoline-6-yloxyalkanoic acid amides for use primarily as plant fungicides. Thus, according to the present invention there is provided a compound of the General Formula I (1) where Q1, Q2 and Q3, independently of each other, are Ref. 200204 halogen, cyano, nitro, azido, optionally substituted (Ci-S) alkyl, optionally substituted (C3-6) cycloalkyl, optionally substituted heterocyclyl (C3-s), containing at least one heteroatom selected from sulfur, oxygen or NR ° wherein R ° is hydrogen or optionally substituted (Ci-6) alkyl, (C3-6) cycloalkyl optionally substituted (C1-4) alkyl, optionally substituted (C2-6) alkenyl, optionally substituted (C2-6) alkynyl, alkoxy (Ci-β) optionally substituted, optionally substituted (C 2-6) alkenyloxy, optionally substituted (C 2-6) alkynyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylalkyl (Ci-6), arylalkoxy (Ci 6) optionally substituted, optionally substituted heteroaryl, optionally substituted heteroaryloxy, optionally substituted heteroarylalkyl (Ci ~ 6), optionally substituted heteroarylalkoxy (???), -SF5 or -S (O) alkyl (C1-6), where u is 0.1 or 2 and the group alkyl or is optionally substituted with halogen, or Q1, Q2 and Q "independently of each other, are -OS02alkyl (Ci-4), wherein the alkyl group is optionally substituted with halogen, or Q1 r Q2 and Q3f independently of each other, are -CONRuRv, -CORu, -C02Ru, -CRU = NRV, -NRURV, -NRuCORv, -NRuC02Rv, -S02NRuRv or -NRuS02Rw, where Rw is optionally substituted alkyl (Ci-6) and Ru and Rv, independently of each other, They are hydrogen or (Ci ~ 6) alkyl optionally substituted with halogen, or, in the case of -CONRuRv or -S02NRuRv, RURV can be joined to form a 5- or 6-membered carbocyclic or heterocyclic ring containing a heteroatom selected from sulfur, oxygen and NR °, where R ° is hydrogen or optionally substituted alkyl (Ci-6), or, in the case of -CRU = NRV, Rv is optionally substituted hydroxy or (Ci-6) alkoxy, optionally substituted aryloxy or optionally substituted heteroaryloxy , or Q1 and Q2, independently of one another, further indicate hydrogen, R1 is optionally substituted (Ci-4) alkyl, optionally substituted (C2-4) alkenyl, optionally substituted (C2-4) alkynyl or (C3-4) cycloalkyl optionally substituted, R2 is hydrogen, alkyl (Ci-8), cycloalkyl (C3-4), alkenyl (C2-8) iocyano, hydroxy, alkoxy, cyano (C1-4) alkyl, alkoxy (C1-4) alkyl (C1 -4), (C 1-4) alkoxy (C 1-4) alkoxy (C 1-4) alkyl or benzyloxyalkyl (C 1-4), where the phenyl ring is optionally substituted with (C1-4) alkoxy, R3 is - (CRaRb) p (CRcRd) q (X) r (CReRf) sR4, where Ra, Rb, Rc, Rd, Re and Rf, independently of each other, are hydrogen, (1-4C) alkyl, halogen, cyano, hydroxy, (1-4C) alkoxy or (1-4C) alkoxycarbonyl, or RaRb, RcRd or ReRf can be attached to form a ring carbocyclic or heterocyclic of 3 to 8 members containing a heteroatom selected from sulfur, oxygen and NR °, where R ° is hydrogen or optionally substituted alkyl (Ci-e), X is (CO), (C0) 0.0 (C0) ), 0, S (0) t, where t is 0, lo 2, or X is NH or Nalkyl (Ci-6), p, r and s, independently of one another, are 0 or 1, q is 0, 1 or 2, R4 is optionally substituted (Ci-6) alkyl, optionally substituted (C2-e) alkenyl, -CRUU = NRVV, where Ruu is hydrogen or (Ci-6) alkyl and Rvv is optionally substituted hydroxy or (Ci-6) alkoxy, optionally substituted aryloxy or optionally substituted heteroaryloxy, or -CH2 ~ C = C-R5, where R5 is hydrogen, alkyl (Ci-8) optionally substituted with halogen, hydroxy, alkoxy (Ci-6), alkoxy (Ci-3) alkoxy (1-3C), cyano, (1-4C) alkyloxyloxy, aminocarbonyloxy, mono- or di-alkyl (C 1-4) aminocarbonyloxy, trialkyl (C 1-4) silyloxy or -S (O) galkyl (? -e), where g is 0, 1 or 2, or R 5 is (C 3-6) cycloalkyl optionally substituted with halogen , hydroxy, (C 1-6) alkoxy, (C 1-3) alkoxy (C 1-3) alkoxy, cyano, C 1-4 alkyl carbonyloxy, aminocarbonyloxy, mono- or dialkyl (C 1-4) aminocarbonyloxy, trialkyl (C 1-4) 4) silyloxy or -S (O) galkyl (Ci-6), where g is 0, 1 or 2, or R 5 is (C 3-6) cycloalkyl (C 1-4) alkyl, wherein the alkyl and / or cycloalkyl portion is optionally replaced with halogen, hydroxy, (Ci-6) alkoxy, (1-3C) alkoxy (1-3C) alkoxy, cyano, (1-4C) alkyloxycarbonyloxy, aminocarbonyloxy, mono- or dialkyl (1-4C) aminocarbonyloxy, trialkyl ( C1-) silyloxy or -S (0) galkyl (Ci-6), where g is 0, 1 or 2, or R5 is optionally substituted aryl, arylalkyl (C1-4) optionally substituted, aryloxyalkyl (Ci ~ 4) optionally substituted optionally substituted heteroaryl or optionally substituted (C1-4) heteroarylalkyl or optionally substituted (C1-4) heteroaryloxyalkyl, or R4 is optionally substituted (C3-6) cycloalkyl, optionally substituted (C5-6) cycloalkenyl, optionally substituted aryl, heteroaryl optionally substituted or an optionally substituted 5 to 8 membered ring optionally containing a heteroatom selected from sulfur, oxygen or NR °, where R ° is hydrogen or optionally substituted (C1-6) alkyl, or when R3 is - (CRaRb) p ( CRcRd) q (X) r (CReRf) SR4, R2 and R3 can be joined to form an ani 5- or 6-membered ring optionally substituted with halogen, (1-4C) alkyl, mono- or di (C1-4) alkylaminocarbonyl, and optionally containing a heteroatom selected from sulfur, oxygen and NR °°, where R ° ° is (C 1-4) alkyl optionally substituted with halogen, (C 1-6) alkoxy or cyano, or R 00 is phenyl optionally substituted with nitro, (C 1-4) alkyl, (C 1-4) haloalkyl, (C 1-4) alkyl carbonyl or heteroaryl, or R2 and R3 can be join to form an optionally substituted 6.6-membered bicyclic R3 is - (CR30R40) C = CR50, where R30 and R40, independently of each other, are hydrogen, alkyl (i ~ s), haloalkyl (Ci-4), alkoxy (Ci-4) alkyl (Ci-3), alkenyl (C 2-3) or alkynyl (C 2-3), or R 30 and R 40 are linked with the carbon atom to which they are attached to form a carbocyclic or heterocyclic ring of 3 to 6 members containing a heteroatom selected from sulfur, oxygen or NR000, where R °° is hydrogen or (1-4C) alkyl, wherein the carbocyclic or heterocyclic ring is optionally substituted with halo or alkyl (Ci-4), R50 is hydrogen, optionally substituted (C1-4) alkyl, optionally substituted (C3-6) cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl containing a heteroatom selected from sulfur, oxygen or NR °°, where R00 ° is hydrogen or (C1-6) alkyl, L is sulfur or oxygen, and n is 0, 1 or 2, and salts and N-oxides of the compounds of the formula I. The compounds of the invention contain at least one asymmetric carbon atom and can exist as enantiomers (or as pairs of diastereomers) or as mixtures thereof. Also, when n is 1, the compounds of the invention are sulfoxides, which can exist in two enantiomeric forms, and the adjacent carbon can also exist in two enantiomeric forms. The compounds of General Formula (I) can therefore exist as racemates, diastereoisomers, or single enantiomers, and the invention includes all possible isomers or mixtures of isomers in any proportion. It is believed that for any given compound, one isomer may be more active as a fungicide than another. The N-oxides of the compounds of Formula I preferably indicate the N-oxides formed by the quinoline moiety. The salts that the compounds of Formula I can form are preferably those formed by the interaction of these compounds with acids. The term "acid" comprises mineral acids such as hydrogen halides, sulfuric acid, phosphoric acid, etc., as well as organic acids, preferably the commonly used alkanoic acids, for example formic acid, acetic acid and propionic acid. Except where otherwise indicated, alkyl groups and alkyl portions of alkoxy, alkylthio, etc., are suitable to contain from 1 to 6, usually from 1 to 4, carbon atoms in the form of straight or branched chains. Examples are methyl, ethyl, n- and iso-propyl and n-, sec-, iso- and tere- butyl. When the alkyl portions contain 5 or 6 carbon atoms, examples are n-pentyl and n-hexyl. Suitable examples of optional substituents of alkyl groups and portions include halo, hydroxy, (C 1-4) alkoxy and (C 1-4) alkoxy (C 1-4) alkoxy, cyano, optionally substituted aryl and optionally substituted heteroaryl. Where the optional substituent is halo, the haloalkyl group or moiety is usually monochloromethyl, monofluoromethyl, dichloromethyl, difluoromethyl, trichloromethyl or trifluoromethyl. Except where otherwise indicated, the alkenyl and alkynyl portions also conveniently contain from 2 to 6, usually from 2 to 4, carbon atoms in the form of straight or branched chains. Examples are allyl, ethinyl and propargyl. Optional substituents include halo, alkoxy, optionally substituted aryl, and optionally substituted heteroaryl. Halo includes fluoro, chlorine, bromine and iodine. Aryl is generally phenyl but also includes naphthyl, anthryl and phenanthryl. Heteroaryl is usually an aromatic ring of 5 or 6 members containing one or more sulfur, oxygen or NR portions as heteroatoms, which may be fused to one or more other aromatic or heteroaromatic rings, such as a benzene ring. Examples are thienyl, furyl, pyrrolyl, isoxazolyl, oxazolyl, thiazolyl groups, oxadiazolyl, pyrazolyl, imidazolyl, triazolyl, isothiazolyl, tetrazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, indolyl, quinolyl, isoquinolyl, quinazolinyl and quinoxalinyl and, when correspond, N-oxides and salts thereof. Any of the aryl or heteroaryl values is optionally substituted. Except where otherwise indicated, substituents that may be present include one or more of the following: halo, hydroxy, mercapto, (Ci-6) alkyl (especially methyl and ethyl), (C 2-6) alkenyl (especially allyl) , (C2-6) alkynyl (especially propargyl), (Ci -6) alkoxy (especially methoxy), (C2-6) alkenyloxy (especially allyloxy), (C2-6) alkynyloxy (especially propargyloxy), haloalkyl (Ci-d) ) (especially trifluoromethyl), haloalkoxy (Ci-6) (especially trifluoromethoxy), S (O) malky (Ci-6) where m is 0, 1 or 2 and the alkyl is optionally substituted with halo, hydroxyalkyl (Ci-6) , alkoxy (Ci-4) alkyl (Ci-4), alkoxy (C 1-4) alkoxy (C 1-4), cycloalkyl (C 3 -s), cycloalkyl (C 3-6) alkyl (C 1-4), aryl optionally substituted (especially optionally substituted phenyl), optionally substituted heteroaryl (especially optionally substituted pyridyl or pyrimidinyl), optionally substituted aryloxy (especially optionally substituted phenoxy), optionally substituted heteroaryloxy (especially optionally substituted pyridyloxy or pyrimidinyloxy), -S (0) optionally substituted maryl wherein m is 0, 1 or 2 (especially optionally substituted phenylthio), -S (0) optionally substituted m-heteroaryl where m is 0, 1 or 2 (especially optionally substituted pyridylthio or pyrimidinylthio), optionally substituted arylalkyl (Ci-4) (especially optionally substituted benzyl, optionally substituted phenethyl and optionally substituted n-propyl phenyl) in which the alkyl portion is optionally substituted with optionally substituted hydroxy, heteroarylalkyl (Ci-4) (especially optionally substituted pyridyl- or pyrimidinyl (C 1-4) alkyl), optionally substituted aryl (C 2-4) alkyl (especially optionally substituted phenylethenyl), optionally substituted heteroaryl (C 2-4) alkyl (especially pyridiletenyl or optionally substituted pyrimidinylenyl), arylalkoxy (C1-4) optionally substituted (especially benzyloxy and optionally substituted phenethyloxy), optionally substituted heteroarylalkoxy (C1-4) (especially pyridylalkoxy (C1-4) or optionally substituted pyrimidinylalkoxy (C1-4)), aryloxyalkyl (C1.4) optionally substituted (especially phenoxymethyl), optionally substituted (C1-4) heteroaryloxyalkyl (especially pyridyloxy or pyrimidinyloxyalkyl (C1-4)) optionally substituted), -S (0) optionally substituted aryl (C 1-4) where m is 0, 1 or 2 (especially optionally substituted benzylthio and phenethylthio), S (0) maloyne (Ci-4) optionally substituted heteroaryl where m is 0, 1 or 2 (especially optionally substituted pyridylalkylthio (C 1-4) or pyrimidinylalkylthio (C 1-4) alkyl) optionally substituted (C 1-4) S (0) alkyl wherein m is 0, 1 or 2 (especially phenylthiomethyl) , (C 1-4) alkyl S (0) optionally substituted m-heteroaryl where m is 0, 1 or 2 (especially optionally substituted pyridyldioalkyl (C 1-4) or pyrimidinylthioalkyl (C 1-4), acyloxy, including (C 1-6) alkanoyloxy; 4) (especially acetyloxy) and benzoyloxy, cyano, isocyano, thiocyanate, isothiocyanate, nitro, NRgRh, -NHCOR9, -NHC0NR9Rh, -C0NRgRh, -C02R9, -SC ^ R1, -0S02Ri, -COR9, -CR9 = NR or - N = CR9Rh in which R1 is (C1-4) alkyl, (C1-4) haloalkyl, (C1-4) alkoxy, halo (C1-4) alkoxy, (C1-4) alkylthio, (C3-6) cycloalkyl ), cycloalkyl ( C3-6) (1-4C) alkyl, phenyl or benzyl, the phenyl and benzyl groups are optionally substituted with halogen, (1-4C) alkyl or (1-4C) alkoxy and R9 and Rh are independently hydrogen, alkyl (C1) -4), haloalkyl (0? -4), (C1-4) alkoxy, halo (C1-) alkoxy / (C1-4) alkylthio, (C3-6) cycloalkyl, (C3-6) cycloalkyl (C1) -4), phenyl or benzyl, the phenyl and benzyl groups are optionally substituted with halogen, (1-4C) alkyl or (1-4C) alkoxy.
Of particular interest are those compounds of Formula (I), wherein Q2 is hydrogen, Q1 and Q3 are as mentioned above. Another group of preferred compounds of Formula (I) are those wherein Q 1 is halogen, aryl or heteroaryl, Q 2 is hydrogen and Q 3 is as mentioned above. Another group of preferred compounds of Formula (I) are those wherein Q 1 is aryl, Q 2 is hydrogen and Q 3 is as defined above. Another group of preferred compounds of the Formula (I) are those where Q1 is heteroaryl, Q2 is hydrogen and Q3 is as defined above. Another group of preferred compounds of Formula (I) are those where Q1 and Q3 are halogen and Q2 is hydrogen. Another group of preferred compounds of the Formula (I) are those where Q1 is aryl or heteroaryl, Q2 is hydrogen and Q3 is halogen. Another group of preferred compounds of Formula (I) are those wherein Q1 and Q2 are hydrogen and Q3 is halogen or optionally substituted alkyl. Another group of preferred compounds of Formula (I) are those wherein Q 1 is halogen, Q 2 is hydrogen and Q 3 is optionally substituted alkyl. Another group of preferred compounds of Formula (I) are those where Q 1 and Q 2 are halogen and Q 3 is alkyl optionally substituted. Another group of preferred compounds of Formula (I) are those wherein Q 1 is bromine. Another group of preferred compounds of Formula (I) are those where Q 1 is iodine. Another group of preferred compounds of Formula (I) are those where Q 1 is chloro. Another group of preferred compounds of Formula (I) are those wherein Q 1 is fluoro. Another group of preferred compounds of Formula (I) are those wherein Q3 is halogen. Another group of preferred compounds of Formula (I) are those wherein Q3 is fluoro. Another group of preferred compounds of Formula (I) are those wherein Q 1 is bromine, Q 2 is hydrogen and Q 3 is fluoro. Another group of preferred compounds of Formula (I) are those wherein Q 1 is bromine, Q 2 is hydrogen and Q 3 is chlorine. Another group of preferred compounds of Formula (I) are those wherein Q 1 is iodine, Q 2 is hydrogen and Q 3 is fluoro. Another group of preferred compounds of Formula (I) are those where Q 1 is iodine, Q 2 is hydrogen and Q 3 is chlorine.
Another group of preferred compounds of Formula (I) are those wherein Q 1 is hydrogen, halogen, aryl or heteroaryl. Another group of preferred compounds of Formula (I) are those wherein R 1 is alkyl (Ci-4) or haloalkyl (0 -4). Another group of preferred compounds of Formula (I) are those wherein R 1 is methyl. Another group of preferred compounds of Formula (I) are those wherein R 1 is ethyl. Another group of preferred compounds of the Formula (I) are those where R2 is hydrogen or methyl. Another group of preferred compounds of Formula (I) are those wherein R 2 is hydrogen. Another group of preferred compounds of Formula (I) are those wherein Q1, Q2 and Q3 are halogen. Another group of preferred compounds of Formula (I) are those wherein Q 1 is halogen, Q 2 is (C 1-4) alkyl and Q 3 is halogen. Another group of preferred compounds of Formula (I) are those wherein Q 1 is halogen, Q 2 is (C 1-4) alkyl and Q 3 is chloro. Another group of preferred compounds of Formula (I) are those wherein Q 1 is halogen, Q 2 is (C 1-4) alkyl and Q 3 is fluoro. Another group of preferred compounds of the Formula (I) are those where Q1 is halogen, Q2 is methyl and Q3 is halogen. Another group of preferred compounds of Formula (I) are those wherein Q 1 is halogen, Q 2 is methyl and Q 3 is chloro. Another group of preferred compounds of Formula (I) are those wherein Q 1 is halogen, Q 2 is methyl and Q 3 is fluoro. Another group of preferred compounds of Formula (I) are those wherein Q 1 is bromine, Q 2 is methyl and Q 3 is chlorine. Another group of preferred compounds of Formula (I) are those wherein Q 1 is bromine, Q 2 is methyl and Q 3 is fluoro. Another group of preferred compounds of Formula (I) are those wherein Q 1 is iodine, Q 2 is methyl and Q 3 is chlorine. Another group of preferred compounds of Formula (I) are those where Q 1 is iodine, Q 2 is methyl and Q 3 is fluoro. Another group of preferred compounds of Formula (I) are those wherein Q 1 is halogen, Q 2 and Q 3 are a 1 qu i 1 or (Ci-4). Another group of preferred compounds of Formula (I) are those wherein R 3 is tere-butyl, 1-halo-2-methylprop-2-yl, 1,1-dihalo-2-methylprop-2-yl, 1, 1, l-trihalo-2-methylprop-2-yl, 1-a-1-coxy-2-methylprop-2-yl, l-alkenyloxy-2-methylprop-2-yl, 1-a 1-qu ini-1-oxy 2 - . 2-me ti lpr op-2-i 1 o, 1-cyano-2-methyl-1-pr or-2-y 1, 1-alkoxyalkoxy-2-methyl-prop-2-yl, l-halo -3-methylbut-3-yl, 1, l-dihalo-3-methylbut-3-yl, 1, 1, 1 r iha 1 o- 3 -methylbut-3-yl, l-alkoxy-3-met ilbut-3-yl, 1-alkenyloxy-3-methylbut-3-yl, 1-a 1 qu ini 1 ox i -3-methylbut-3-yl, 1-cyano-3-methyl ti-3-i It is 2-cyanoprop-2-yl, 2-methoxycarbonyl-2-yl or 2-methylaminocarbonylprop-2-yl, 1-a l and 11-o-2-met i-prop-2. ilo, 1-alkylsulfinyl 1 - 2-methyl-1-propyl-2-yl, 1-a 1-yl-1-yl-1-2-methyl-2-yl, 2-cyano- l-alkoxyprop-2-ylo, 2-methyl-1 - 1 - [(E and / or Z) -hydroxyimino] -prop-2-yl, 2-methyl-1 - 1 - [(E and / or Z ) -alkoxyimino] -prop-2-yl, 2 -me ti 1 - 1 - [(E and / or Z) -ari lox i imi no] -pr op- 2 - i 1 o, 2-met i 1- 1 - [(E and / or Z) -hether or to 1-oximino] -pr op-2-i 1 or, 1-alkoxy-prop-2-yl, 1 -ha 1 or -prop-2 - i lo, 3 -me ti 1 -bu t - 1 -in-3-yl, 1 to 1 qui 1 - 3 -me ti 1 -but - 1 - i n- 3 - i 1 o, 4-methyl-pent-2-in-4-yl, 1 -hi drox i - -me ti 1 -pen t - 2-in- 4 - i 1 o, 1-alkoxy-4-methyl-pent-2-yn-4-yl, l-alkoxyalkoxy-4-methyl-pent-2-yn-4-yl, l-alkoxyalkoxyalkyl- 4-methyl-pent-2-yn-4-yl, 1-cyan-1-yl-1 -3-methyl-l-butyl-3-yl, o-1-haloalkyl-3-methylbut-3-yl, and more preferably , wherein R3 is tere-butyl, l-halo-2-methylprop-2-yl, 1-fluoro-2-methylprop-2-yl, 1 -me toi-2 -me ti lp r op-2-i 1 or , l-ethoxy-2-methylprop-2-yl, l-allyloxy-2-methylprop-2-yl, 1- (prop-2-ynyloxy) -2-methyl t-p r o-2-y 1 o, 2 -ciano-l- et ox i -prop- 2-i lo, 2-cy ano- 1 -me t oxypr op-2-i 1 o, 1-halo-3-methylbut-3-yl, 1-f luoro-3-methylbut- 3-yl, 3-methylbut-l-in-3-yl, 4-methylpent-2-yn-4-yl, 5-methyl-hex-3-yn-5-yl, l-methoxy-4-methyl- pent-2-in-4-yl, 1-a 1 i loxi-4-methyl-1 -pent-2-in-4-yl, 1-pr ope rgi 1 ox i-4-methyl-pent-2 -in- -yl, l-ethoxy-4-methyl-pent-2-yn-4-yl. Another group of preferred compounds of Formula (I) are those wherein R 4 is (Ci-6) alkyl optionally substituted with alkoxy (Ci-4) alkoxy (Ci-4) alkyl (Ci-4), wherein the alkyl group is optionally substituted with halo, mono- or di-alkyl (Ci ~ 6) amino or trialkyl (Cj.-4) silyl, or R4 is (Ci-6) alkyl optionally substituted with benzyloxyalkyl (Ci ~ 4) ), wherein the alkyl group is optionally substituted with halo, mono- or di-alkyl (Ci ~ 6) amino or trialkyl (C 1-4) silyl, or R 4 is alkyl (Ci ~ 6) optionally substituted with alkenyloxy (C 2-6) ) or -S (O) xalkyl (??? 6), where x is 0, 1 or 2 and the alkyl group is optionally substituted with halo, mono- or di-alkyl (Ci-e) amino, -NHalkyl (Ci ~ 4) = NOR, where R is hydrogen or alkyl (Ci ~ 4), or where the alkyl group is optionally substituted with trialkyl (Ci ~) silyl, or R4 is -CRUU = NRVV, where Ruu is hydrogen or alkyl (Ci) -6) and Rvv is optionally substituted hydroxy or alkoxy (Ci ~ 6). Another group of preferred compounds of Formula (I) are those wherein the rings or optionally substituted aryl portions and heteroaryl optionally substituted of R 5 values are optionally substituted with halogen, cyano, nitro, azido, alkyl (Ci 6), haloalkyl (Ci 6), cycloalkyl (C 3-6), cycloalkyl (C 3-6) alkyl (C 1-4), alkenyl (C2 ~ 6) / haloalkenyl (C2-e) < alkynyl (C2-6), haloalkynyl (C2-6), alkoxy (Ci-6), haloalkoxy (C-e), alkenyloxy (C2-6), haloalkenyloxy (C2-6), alkynyloxy (C2-6), haloalkynyloxy (C2-6) # · aryl, aryloxy, arylalkyl (Ci-6), arylalkoxy (Ci-6), heteroaryl, heteroaryloxy, heteroarylalkyl (Ci-6), heteroarylalkoxy (Ci-e), -SF5, -S (O ) galkyl (Ci-4) where g is 0, 1 or 2 and the alkyl is optionally substituted with halo, or R5 is optionally substituted with -OS02alkyl (Ci-4), where the alkyl group is optionally substituted with halo, or R5 is optionally substituted with -CONRgRh, -CORg, -C02Rg, -Rg = NRh, -NRgRh, -NRgCORh, -NRgC02Rh, -S02NRgRh or -NRgS02Ri, where R1 is alkyl (Ci-6) optionally substituted with halogen and Rg and Rh , independently of one another, are hydrogen or (Ci ~ 6) alkyl optionally substituted with halogen, or, in the case of -CONRgRh or -S02NRgRh, RgRh can be joined to form a 5- or 6-membered carbocyclic or heterocyclic ring containing a hetero volume selected from sulfur, oxygen or NR °, where R ° is hydrogen or optionally substituted alkyl (Ci-6). Another group of preferred compounds of Formula (I) are those wherein the optionally substituted aryl ring, optionally substituted heteroaryl or from 5 to 8 optionally substituted R4 is optionally substituted with halogen, cyano, nitro, azido, alkyl (Ci-6), haloalkyl (Ci-6), cycloalkyl (C3-6), cycloalkyl (C3-6) alkyl (C1-4), alkenyl (C2-6) haloalkenyl (C2-6), alkynyl (C2-6), haloalkynyl (C2-6) / alkoxy (?? -e), haloalkoxy (Ci-6), alkenyloxy (C2-6) haloalkenyloxy ( C2-6), alkynyloxy (C2-6) ha 1 or 1 qu i ni 1 ox i (C2 - 6) ~ SF5, -S (0) xa 1 qu i 1 o (Ci - 6), where x is 0 , 1 or 2 and the alkyl group is optionally substituted with halo, or R4 is optionally substituted by -OS02a 1 qu i 1 or (Ci-4), where the alkyl group is optionally substituted with halogen, -CONRxRy, -CON (ORx ) Ry, -CORx, -C02Rx, -CRx = NRy, -NRxRy, -NRxCORy, -NRxC02Ry, -S02NRxRy or -NRxS02R% where Rz is alkyl (Ci-g) optionally substituted with halogen and Rx and Ry, independently one of the another, are hydrogen or alkyl (Ci-e) optionally substituted with halogen. Another group of preferred compounds of Formula (I) are those wherein R50 is (C1-4) alkyl optionally substituted with halogen, hydroxy, (Ci ~ 6) alkoxy to 1 queni 1 or (C2-6) (especially allyl), alkynyl (C2-6) (especially propargyl), alkoxy (Ci-4) alkoxy (C1-4), cyano, a 1 qu i 1 (C 1-4) ca rbon i 1 oxy, aminoca rboni 1 ox i, mono - or di (C1-4) alkyl amino-carbonyloxy, S (O) pa 1 qu i 1 or (Ci-6), where p is 0, 1 or 2, triazolyl, pyrazolyl, imidazolyl, trialkyl (Ci ~ 4) silyloxy, optionally substituted phenoxy, optionally substituted thienyloxy, optionally substituted benzyloxy or optionally substituted thienylmethoxy. Another group of preferred compounds of the Formula (I) are those in which R50 is cyc 1 or to 1 qui 1 or (C3 -6) optionally substituted with halogen, hydroxy, a 1 cox i (Ci-6), a 1 cox i (Cx-4) to 1 cox i (Ci -4), cyano, a 1 qu i 1 (Ci ~ 4) carboni 1 ox i, aminocarbonyloxy, mono- or di-a 1 qui lo (Ci ~ 4) amino-ca rbon i loxi, S (O ) palquilo (Ci-6), where p is 0, 1 or 2, triazolyl, pyrazolyl, imidazolyl, trialkyl (C 1-4) silyloxy, optionally substituted phenoxy, optionally substituted thienyloxy, optionally substituted benzyloxy or optionally substituted thienylmethoxy. Another group of preferred compounds of Formula (I) are those wherein the optionally substituted aryl or the optionally substituted heteroaryl R50 is optionally substituted with halogen, hydroxy, mercapto, (C1-4) alkyl, (C2-) alkenyl, alkynyl (C2) -4), (C 1-4) alkoxy, (C 2-4) alkenyloxy, (C 2-4) alkynyloxy, ha lo 1 (Ci -4), haloalkoxy (C 1-4), alkyloi (Ci -4) ), which has 1 to 11 (Ci -4), hydroxyalkyl (Ci ~ 4), (C 1-4) alkoxy (C 1-4) alkyl, (C 3-6) cycloalkyl, cycloalkyl (C 3-6) a lqui lo (Cx -4), phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanate, isothiocyanate, nitro, NRpRq, NHCORp, -NHCONRpRq, CONRpRq, -S02R °, OS02R °, CORp, CRp = NRq or N = CRpRq, where R ° is (C 1-4) alkyl, haloalkyl (Cx-4), alkoxy (Cx-4), haloalkoxy (Ci-4), alkylthio (C 1-4), cycloalkyl (C 3-6), cycloalkyl (C 3-6) alkyl (C 1-4), phenyl or benzyl, the phenyl and benzyl groups are optionally substituted with halogen, (1-4C) alkyl or (C -4) alkoxy, and Rp and Rq are independently hydrogen, (1-4C) alkyl, (1-4C) haloalkyl, alkoxy (C 1-4), haloalkoxy (C 1-4), alkylthio (Ci 4), cycloalkyl (C 3-6), cycloalkyl (C 3-6) alkyl (C 1-4), phenyl 0 benzyl, the phenyl and benzyl groups are optionally substituted with halogen, (1-4C) alkyl or (1-4C) alkoxy. Another group of preferred compounds of Formula (I) are those where L is oxygen. Another group of preferred compounds of the Formula (I) are those where n is 0. Another group of preferred compounds of Formula (I) are the N-oxides formed by the quinoline moiety in the compounds of Formula I. The compounds forming part of the invention are illustrated in Tables 1 to 192 below. In the Examples 1 to 5 indicate the melting points (pf) and / or the diagnostic molecular ion values (eg M +, [+ l] +) and / or the spectroscopic data (1H NMR) while the biological activities are indicate in Example 6.
Table 1 The compounds of Table 1 are of the General Formula (I) where Q1 is chlorine, Q2 is hydrogen, Q3 is chlorine, n is 0, L is O, R1 is methyl, and R2 and R3 have the values indicated in the board. 22 H 2, 4-dimethyl-pent-2-yl 23 H 2, 4, 4-trimethyl-but-2-yl 24 H 2,4, 4-trimethyl-pent-2-yl 25 H Cl-n-C3H6- 26 H C1-CH2 (CH3) 2C- 5 27 H F3C (CH3) 2C- 28 H NC-CH2- 29 CH3 NC-CH2- 30 NC-CH2- NC-CH2- 31 H (NC) 2CH- 32 H NC-C2H4- 10 33 CH3 NC-C2H4-34 NC-C2H4- NC-C2H4-35, H (CH3) 2C (CN) - 36H C2H5 (CH3) C (CN) - 37 H (C2H5) 2C (CN) -38 H (CH3) 2CH (CH3) C (CN) -15 H H -CH2 (CH3) 2C- 40 H HO-C2H4 (CH3) 2C-1-hydroxy-2H 41 H (hydroxymethyl) -prop-2-yl l-hydroxy-2- (methoxy-42 H methyl) prop-2-yl 20 l-methoxy-2- (methoxy-43 H methyl) prop-2-yl l- hydroxy-2- 44 H (hydroxymethyl) -but-2-yl 45 C2H OC2H4 - C2H5OC2H4- 46 CH3 (CH3O) 2CHCH2- 47 H CH 3 O -CH 2 (CH 3) 2 C- 48 H CH 3 O-C 2 H 4 (CH 3) 2 C- 49 H C 2 H 50 -C 2 H 4 (CH 3) 2 C- 50 H CH 3 S -CH 2 (CH 3) 2 C- 51 H NC- (CH 3 O) CH- 5 52 H CH3OCH2 (CH3) C (CN) - 53 H CH3SCH2 (CH3) C (CN) - 54 H CH3 (CO) (CH3) 2C- 55 H CH3CHBr (CO) (CH3) 2C- 56 H CH3 (CO ) (OH) CH (CH3) 2C- 57 H CH3OC2H4 (CO) (CH3) 2C- 10 58 H CH3 (CO) CH2 (CH3) 2C- 59 H CH30 (CO) (CH3) CH- 60 H CH30 (CO ) (CH3) 2C- 61 H C2H50 (CO) C2H4-62H CH3NH (CO) (CH3) 2C- 63 H (CH3) 2N (CO) (CH3) 2C- 15 64 H (CH3) 3SiCH2- tert-C4H9 (CH3) 2 SiO- 65 H CH2 (CH3) 2C- tert-C4H9 (CH3) 2SiO- 66 H C2H4 (CH3) 2C- 67 H 4-FPhCH2OCH2 (CH3) 2C- 20 68 H C2H5OCH2 (CH3) 2C-69 H CH 3 OCH 2 CH 2 O (CH 3) 2 C- 70 H CH 2 = CHCH 2 - 71 CH 2 = CHCH 2 - CH 2 = CHCH 2 - 72 H CH 2 = C (CH 3) CH 2 - 73 H CH 2 = CH (CH 3) CH - 74 H CH 2 = CH (CH 3) 2 C- 75 H CH 3 (CO) CH = CH- 76 CH 3 CH 3 (CO) CH = CH- 77 H pent-3-en-2-yl 2-methyl-hex-3-en -2-ilo 78 H (E) 2-methyl-hex-3-en-2-yl 79 H (Z) 2-methyl-pent-4-en-3-on-2- 80 H ilo 81 H CH30 (CO) CH = (Cl) C (CH3) 2C- 82 H C6H5-C (CH3) = CH (CH3) 2C- 83 CH2 = CHCH2- CH2 = CHCH2OC2H4-84 H CH = CCH2-85 CH3 CH = CCH2-86 H cycloprop-1-yl 87 NC-C2H4- cycloprop-1-yl 88 cycloprop-1-yl cycloprop-1-yl 89 H 1-cyano-cycloprop-1-yl 90 H 2-cyano-cycloprop-1-yl 1-methoxycarbonyl-91 H cyclopropyl 1- [N, N-dimethylamino-92 H carbonyl] -cycloprop-1-yl 1- [N-methyl-N- methoxy-93 H aminocarbonyl] -cyclopropyl-yl 1-cyano-l-cyclopropyl-et- 94 H 1 -yl 95 H cyclopent-l-yl 96 H 1-cyano-cyclopent-l-yl 97 H cyclohex-l-yl 98 CH2 = CHCH2- cyclohex-l-yl 99 H 4-cyano-cyclohex-l-yl l-cyano-4-methyl-cyclohex- 100 H 1 -yl-tert-butyl-l- cyano- 101 H cyclohex-l-yl 2-methyl-3- 102 H cyanotetrahydrofuran-3-yl 5-methyl-l, 3-dioxolan-5- 103 H ilo 104 H 5-ethyl-l, 3-dioxolan -5-yl 3, 5-dimethyl-l, 3-dioxolan-105 H 5-yl N-ethoxycarbonyl-piperid-106 H 4-yl 107 H morpholino 108 H cyclohex-l-yl-methyl 109 H 4-cyano-cyclopenten-3-yl 5-tert-butyl-2H-1, 3, 4- 110 H thiadiazin-2-yl 2- (cyclohexan-1-yl) -et-1- 111 H yll 112 H fur-2-yl 5-methoxycarbonyl-fur-2- 113 H yl 162 H 3-I-CgH4CH2- 163 H 3-CH3-C6H4CH2- 164 H 3-CH30-C6H4CH2- 165 H 4-F-C6H4CH2- 166 H 4-Cl-C6H4CH2- 167 H 4-CH3-C6H4CH2- 168 H 4-CF3-C6H4CH2- 169 H 4-CH30-C6H4CH2- 170 H 4-CF30-C6H4CH2- 171 H 2, 6-di-F-C6H3CH2- 3-methyl-but-2- 172 2, 5-di-F -C6H3CH2- en-l-yl 173 H 2 -F-4-Cl-C6H3CH2- 174 H 2 -F-6-Cl-C6H3CH2- 175 H 2, 6-di-Cl-C6H3CH2-4 -methyl-pent- 2- 176 3, 4-di-Cl-C6H3CH2- en-l-yl 177 H 2 -F-6-CH30-C6H3CH2- 178 H 2, 4, 5-tri-F-C6H2CH2- 179 H 2, 4- di-Cl-6-CH3-C6H2CH2- 180 H 3, 4, 5-tri-CH30-C6H2CH2- 181 H C6H5-CH (CH3) - 182 H 4-F-C6H4-CH (CH3) - 183 H 4- N02-C6H4-CH (CH3) - 184 H 4-n-pentyl-C6H4-CH (CH3) - 185 H 4-CH3S02-C6H4-CH (CH3) - 186 H C6H5 (CO) CH2- 187 H C6H5-CH (CN) - 188 H C6H5- (CH30) CH- 189 H C6H5- (CH3) 2C-190 H m-Cl-C6H5- (CH3) 2C- 191 H 3, 5-di-Cl-C6H3- (CH3) 2C- 192 H C6H5- (C2H50 (CO)) CH - 193 H phenethyl 3-methoxy-4-propargiloxy- 194 H phenethyl 3-ra- ethoxy-4- (pent-2-in-1-195 H -yloxy) -phenethyl 196 H 2 -methyl-3-phenyl-prop-2- ilo 197 H C6H50-C2H4- 198 H 4-F-C6H4-CH2OCH2 (CH3) 2C- 199H C6H5-CH20 (CO) C2H4- 200 H naphth-2-yl- (CH3) CH- 201 NC-C2H4- pyrid- 3-ylmethyl 202 CH 3 2-pyrid-2-ylethyl-l-2- (3-chloro-5-trifluoromethyl-203 H pyrid-2-yl) oxyeth-l-yl 2-methyl--pyrazin-2-yl -but- 204 H 3-on-2-yl 205 - (CH2) 4- 206"(CH2) 5- 207 - (CH2) 4CH (C2H5) - 208 - C3H6CH [(CO) N (C2H5) 2] CH2 - 209 -CH (CH3) CH = CHCH (CH3) - 210 :: P 211-C2H-OC2H-212-CH2CH (CH3) OCH (CH3) CH2- 213 -C2H4SCH2"- 214 - C2H4SC2H4- 215 - (CH2) 2NH (CH2) 2- 216 - (CH2) 2N (p-N02- C6H4) (CH2) 2- 217 - (CH2) 2N (m-CF3-C6H4) (CH2) 2- 218 - (CH2) 2N (p-CH3CO-C6H4) (CH2) 2- 219 - (CH2) 2N ( pyrid-2-yl) (CH2) 2- 220 H (H2C = CHCH2OCH2) (CH3) 2C-221H (HCCHCH2OCH2) (CH3) 2C- 222H (CH3CH2OCH2) (CH3) 2C- 223H ((CH3) 2CHOCH2 ) (CH3) 2C- 224 H C6H5CH2OCH2 (CH3) 2C- 225 H (CH3CH2OCH2) (CH3) 2C- 226H 4-F-C6H4-CH2 (CH3) C (CN) -227H 4-Cl-C6H4-CH2 (CH3) C (CN) -228H 4-CH30-C6H4-CH2CH2 (CH3) C (CN) -229H 2-Cl-CeH4-CH2 (CH3) C (CN) -230H (CH3) 2CH-CH2 (CH3) C (CN) -231H-1-methoxymethyl-cycloprop-1-yl 1-benzyloxymethyl-cycloprop-1-232 H -yl 1-methoxymethoxy-2-methyl-prop-233 H 2 -yl 235 H 1- cyclopropyl-et-l-yl 236 H 2-fluor-et-l-yl 2,2, 2-trifluor-l-methyl-et-l-237 H yl 238 H HC = CC (CH3) 2- 239 CH3 HC = CC (CH3) 2- 240 H HC = CC (CH2CH3) (CH3) - 241 CH3 HC = CC (CH2CH3) (CH3) - 242 H HC = CC ( CH2CH2) - 243 CH3 HC = CC (CH2CH2) - 244 H (H3C) C = CC (CH3) 2- 245 CH3 (H3C) C = CC (CH3) 2- 246 H (H3C) C = CC (CH2CH3) ( CH3) - 247 CH3 (H3C) C = CC (CH2CH3) (CH3) - 248 H (H3C) C = CC (CH2CH2) - 249 CH3 (H3C) C = CC (CH2CH2) - 250 H (HOCH2) C = CC (CH3) 2-251 H (CH3OCH2) C = CC (CH3) 2-252 H (HOCH2) C = CC (CH3) (CH2CH3) 2-253 H (CH3CH2OCH2) C = CC (CH3) 2-254 H ( CH3OCH2) C = CC (CH3) (CH2CH3) 2-255H (CH3OC2H4OC2H4) C = CC (CH3) 2-256H (Cl-n-C3H6) C = CC (CH3) 2-257H (NC-n- C3H6) C = CC (CH3) 2-258 H (CH3SCH2) C = CC (CH3) 2-259 H (C6H5) C = CC (CH3) 2- 260 H (CH3) 2 (CH30) CC = CC (CH3 ) 2- 261 H (H2C = CHCH2OCH2) (CH3) CH- 262 H (HC = CHCH2OCH2) (CH3) CH- 263 H (CH3CH2OCH2) (CH3) CH- 264 H (CH3OCH2) (CH3) CH- 265 H ( (CH3) 2CHOCH2) (CH3) CH- 266H C6H5CH2OCH2 (CH3) CH- 267 H (CH3CH2OCH2) (CH3) CH- 268 H (CC4H7) CH- 269 H (cC4H7) CH3C- 270 H FCH2 (CH3) CH- 271H CICH2 (CH3) CH- 272 H FCH2CH2 (CH3) CH- 273 H CICH2CH2 (CH3) CH- 274H FCH2 (CH3) 2C- 275H FCH2CH2 (CH3) 2C- 276H C1CH2CH2 (CH3) 2C- 277H CH30 (C2H4) C = CC (CH3) 2- 278H tetrahydro-furan- 2-ylmethyl 1- (tetrahydro-furan-2- 279 H yl) ethyl 1-methyl-1- (tetrahydro-furan-280 H 2 -yl) ethyl 281 H 2- [1, 3] dioxolan-2-yl- ethyl 2- [1, 3] dioxolan-2-yl-l-methyl- 282 H ethyl 2- [1, 3] dioxolan-2-yl-l, 1- 283 H dimethyl-ethyl 284 H prop-1-yl 285 CH3 prop-l-yl 286 H thiophen-3-ylmethyl 287 H 1- (thiophen-3-yl) -et-l-yl 1-methyl-l- (thiophen-3-yl) -et-l-289 H ilo 290 H cyclopent-l-yl 291 H 3-F-C6H4-CH2- 292 H 3-F-C6H4-CH (CH3) -293 H 3-F-C6H4-C (CH3) 2- 294 H C2H5C = CC (CH3) 2- 294 H nC3H7C = CC (CH2CH3) (CH3) - 296 H i-C3H7C = CC (CH2CH2) - 297 H n-C4H9C = CC (CH3) 2- 298 H sec-C4H9C = CC (CH3) 2- 299 H iso -C4H9C = CC (CH3) 2- 300H terc-C4H9C = CC (CH3) 2-301H HOC2H4C = CC (CH3) 2-302H CH3 (CH30) (CH) C = CC (CH3) 2-303H (nC3H7OCH2) C = CC (CH3) 2-304 H (nC3H7OCH2CH2) C == CC (CH3) 2- 305 H (tert-C4H9OCH2) C = CC (CH3) 2-306 H (tert-C H9OCH2CH2) C = CC (CH3) 2-307 H (NCCH2) C = CC (CH3) 2-308 H (NCCH2CH2) C = CC (CH3) 2- 309 H (C6H5OCH2) C = CC (CH3) 2- 310 H (C6H5OCH2CH2) C = CC (CH3) 2- 311 H (4-FC6H5) C = CC (CH3) 2- 312 H (4-ClC6H5) C = CC (CH3) 2- 313 H (4-BrC6H5) C = CC (CH3 ) 2- 314 H (4-CH3-C6H5) C = CC (CH3) 2- 315 H (3-FC6H5) C = CC (CH3) 2- 316 H (3-ClC6H5) C = CC (CH3) 2- 317 H (3-CH3-C6H5) C = CC (CH3) 2- 318 H (2-FC6H5) C = CC (CH3) 2- 319 H (2-ClC6H5) C = CC (CH3) 2- 320 H ( 2-BrC6H5) C = CC (CH3) 2- 321 H (2-CH3-C6H5) C = CC (CH3) 2-322H (thien-2-yl) C = CC (CH3) 2-323H (thien-3-yl) C = CC (CH3) 2 - Table 2 The compounds of Table 2 are of the General Formula (I) where Q 1 is bromine, Q 2 is hydrogen, Q 3 is chlorine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 2 is the same as compound 1 of Table 1 except that in compound 1 of Table 2 Ql is bromine, Q2 is hydrogen, Q3 is chlorine. Similarly, compounds 2 to 323 of Table 2 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 2 Q 1 is bromine, Q 2 is hydrogen, Q 3 is chlorine.
Table 3 The compounds of Table 3 are of the General Formula (I) where Q 1 is iodine, Q 2 is hydrogen, Q 3 is chlorine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 3 is the same as compound 1 of Table 1 except that in compound 1 of Table 3 Q1 is iodine, Q2 is hydrogen, Q3 is chlorine. Similarly, compounds 2 to 323 of Table 3 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 3 Ql is iodine, Q2 is hydrogen, Q3 is chlorine.
Table 4 The compounds of Table 4 are of the Formula General (I) where Q1 is fluoro, Q2 is hydrogen, Q3 is chloro, n is 0, L is O, R1 is methyl, R2 and R3 have the values listed in Table 1. Therefore, compound 1 of the Table 4 is the same as compound 1 of Table 1 except that in compound 1 of Table 4 Q1 is fluoro, Q2 is hydrogen, Q3 is chloro. Similarly, compounds 2 to 323 of Table 4 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 4 Q1 is fluoro, Q2 is hydrogen, Q3 is chloro.
Table 5 The compounds of Table 5 are of the General Formula (I) where Q 1 is chlorine, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 5 is the same as compound 1 of Table 1 except that in compound 1 of Table 5 Ql is chlorine, Q2 is hydrogen, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 5 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 5 Ql is chlorine, Q2 is hydrogen, Q3 is fluoro.
Table 6 The compounds of Table 6 are of the General Formula (I) where Q 1 is bromine, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 6 is the same as compound 1 of Table 1 except that in compound 1 of Table 6 Q1 is bromine, Q2 is hydrogen, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 6 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 6 Q1 is bromine, Q2 is hydrogen, Q3 is fluoro.
Table 7 The compounds of Table 7 are of the General Formula (I) where Q 1 is iodine, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 7 is the same as compound 1 of Table 1 except that in compound 1 of Table 7 Q1 is iodine, Q2 is hydrogen, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 7 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 7 Q1 is iodine, Q2 is hydrogen, Q3 is fluoro.
Table 8 The compounds of Table 8 are of the General Formula (I) where Q 1 is fluoro, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 8 is the same as compound 1 of Table 1 except that in compound 1 of Table 8 Q1 is fluoro, Q2 is hydrogen, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 8 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 8 Q1 is fluoro, Q2 is hydrogen, Q3 is fluoro.
Table 9 The compounds of Table 9 are of the General Formula (I) where Q 1 is hydrogen, Q 2 is hydrogen, Q 3 is chlorine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 9 is the same as compound 1 of Table 1 except that in compound 1 of Table 9 Q1 is hydrogen, Q2 is hydrogen, Q3 is chlorine. Similarly, compounds 2 to 323 of Table 9 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 9 Q1 is hydrogen, Q2 is hydrogen, Q3 is chlorine.
Table 10 The compounds of Table 10 are of the General Formula (I) where Q 1 is hydrogen, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, the compound 1 of Table 10 is the same as compound 1 of Table 1 except that in compound 1 of Table 10 Q1 is hydrogen, Q2 is hydrogen, Q3 is fluoro. Similarly, the compounds 2 to 323 of Table 10 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 10 Q1 is hydrogen, Q2 is hydrogen, Q3 is fluoro.
Table 11 The compounds of Table 11 are of the Formula General (I) where Q1 is hydrogen, Q2 is hydrogen, Q3 is bromine, n is 0, L is O, R1 is methyl, R2 and R3 have the values listed in Table 1. Therefore, compound 1 of the Table 11 is the same as compound 1 of Table 1 except that in compound 1 of Table 11 Q1 is hydrogen, Q2 is hydrogen, Q3 is bromine. Similarly, compounds 2 to 323 of Table 11 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 11 Q1 is hydrogen, Q2 is hydrogen, Q3 is bromine.
Table 12 The compounds of Table 12 are of the General Formula (I) where Q 1 is chlorine, Q 2 is hydrogen, Q 3 is methyl, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 12 is the same as compound 1 of Table 1 except that in compound 1 of Table 12 Q1 is chlorine, Q2 is hydrogen, Q3 is methyl. Similarly, compounds 2 to 323 of Table 12 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 12 Q 1 is chlorine, Q 2 is hydrogen, Q 3 is methyl.
Table 13 The compounds of Table 13 are of the Formula General (I) where Q 1 is bromine, Q 2 is hydrogen, Q 3 is methyl, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of the Table 13 is the same as compound 1 of Table 1 except that in compound 1 of Table 13 Q1 is bromine, Q2 is hydrogen, Q3 is methyl. Similarly, compounds 2 to 323 of Table 13 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 13 Q1 is bromine, Q2 is hydrogen, Q3 is methyl.
Table 14 The compounds of Table 14 are of the General Formula (I) where Q 1 is iodine, Q 2 is hydrogen, Q 3 is methyl, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 14 is the same as compound 1 of Table 1 except that in compound 1 of Table 14 Q1 is iodine, Q2 is hydrogen, Q3 is methyl. Similarly, compounds 2 to 323 of Table 14 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 14 Q1 is iodine, Q2 is hydrogen, Q3 is methyl.
Table 15 The compounds of Table 15 are of the General Formula (I) where Q 1 is fluoro, Q 2 is hydrogen, Q 3 is methyl, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 15 is the same as compound 1 of Table 1 except that in compound 1 of Table 15 Q1 is fluoro, Q2 is hydrogen, Q3 is methyl. Similarly, compounds 2 to 323 of Table 15 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 15 Q1 is fluoro, Q2 is hydrogen, Q3 is methyl.
Table 16 The compounds of Table 16 are of the General Formula (I) where Q 1 is hydrogen, Q 2 is hydrogen, Q 3 is methyl, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, the compound 1 of Table 16 is the same as compound 1 of Table 1 except that in compound 1 of Table 16 Q1 is hydrogen, Q2 is hydrogen, Q3 is methyl. Similarly, the compounds 2 to 323 of Table 16 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 16 Q1 is hydrogen, Q2 is hydrogen, Q3 is methyl.
Table 17 The compounds of Table 17 are of the Formula General (I) where Q 1 is chlorine, Q 2 is hydrogen, Q 3 is chlorine, n is 0, L is O, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of the Table 17 is the same as compound 1 of Table 1 except that in compound 1 of Table 17 R 1 is ethyl, Q 1 is chlorine, Q 2 is hydrogen, Q 3 is chlorine. Similarly, compounds 2 to 323 of Table 17 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 17 R 1 is ethyl, Q 1 is chlorine, Q 2 is hydrogen, Q3 is chlorine.
Table 18 The compounds of Table 18 are of the General Formula (I) where Q 1 is bromine, Q 2 is hydrogen, Q 3 is chlorine, n is 0, L is O, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 18 is the same as compound 1 of Table 1 except that in compound 1 of Table 18 R1 is ethyl, Q1 is bromine, Q2 is hydrogen, Q3 is chlorine . Similarly, compounds 2 to 323 of Table 18 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 18 R 1 is ethyl, Q 1 is bromine, Q 2 is hydrogen, Q3 is chlorine.
Table 19 The compounds of Table 19 are of the Formula General (I) where Q1 is iodine, Q2 is hydrogen, Q3 is chlorine, n is 0, L is O, R1 is ethyl, R2 and R3 have the values listed in Table 1. Therefore, compound 1 of the Table 19 is the same as compound 1 of Table 1 except that in compound 1 of Table 19 R 1 is ethyl, Q 1 is iodine, Q 2 is hydrogen, Q 3 is chlorine. Similarly, compounds 2 to 323 of Table 19 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 19 R 1 is ethyl, Q 1 is iodine, Q 2 is hydrogen, Q3 is chlorine.
Table 20 The compounds of Table 20 are of the General Formula (I) where Q 1 is chlorine, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is O, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 20 is the same as compound 1 of Table 1 except that in compound 1 of Table 20 R1 is ethyl, Q1 is chlorine, Q2 is hydrogen, Q3 is fluoro . Similarly, compounds 2 to 323 of Table 20 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 20 R 1 is ethyl, Q 1 is chlorine, Q 2 is hydrogen, Q3 is fluoro.
Table 21 The compounds of Table 21 are of the Formula General (I) where Q 1 is bromine, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is O, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of the Table 21 is the same as compound 1 of Table 1 except that in compound 1 of Table 21 R1 is ethyl, Q1 is bromine, Q2 is hydrogen, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 21 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 21 R1 is ethyl, Q1 is bromine, Q2 is hydrogen, Q3 is fluoro.
Table 22 The compounds of Table 22 are of the General Formula (I) where Q 1 is iodine, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is O, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 22 is the same as compound 1 of Table 1 except that in compound 1 of Table 22 R1 is ethyl, Q1 is iodine, Q2 is hydrogen, Q3 is fluoro . Similarly, compounds 2 to 323 of Table 22 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 22 R 1 is ethyl, Q 1 is iodine, Q 2 is hydrogen, Q3 is fluoro.
Table 23 The compounds of Table 23 are of the Formula General (I) where Q1 is hydrogen, Q2 is hydrogen, Q3 is chlorine, n is 0, L is O, R1 is ethyl, R2 and R3 have the values listed in Table 1. Therefore, compound 1 of the Table 23 is the same as compound 1 of Table 1 except that in compound 1 of Table 23 R 1 is ethyl, Q 1 is hydrogen, Q 2 is hydrogen, Q 3 is chlorine. Similarly, compounds 2 to 323 of Table 23 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 23 R1 is ethyl, Q1 is hydrogen, Q2 is hydrogen, Q3 is chlorine.
Table 24 The compounds of Table 24 are of the General Formula (I) where Q 1 is hydrogen, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is 0, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 24 is the same as compound 1 of Table 1 except that in compound 1 of Table 24 R1 is ethyl, Q1 is hydrogen, Q2 is hydrogen, Q3 is fluoro . Similarly, compounds 2 to 323 of Table 24 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 24 R1 is ethyl, Q1 is hydrogen, Q2 is hydrogen, Q3 is fluoro.
Table 25 The compounds of Table 25 are of the Formula General (I) where Q1 is chloro, Q2 is hydrogen, Q3 is methyl, n is 0, L is O, R1 is ethyl, R2 and R3 have the values listed in Table 1. Therefore, compound 1 of the Table 25 is the same as compound 1 of Table 1 except that in compound 1 of Table 25 R 1 is ethyl, Q 1 is chlorine, Q 2 is hydrogen, Q 3 is methyl. Similarly, compounds 2 to 323 of Table 25 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 25 R 1 is ethyl, Q 1 is chlorine, Q 2 is hydrogen, Q3 is methyl.
Table 26 The compounds of Table 26 are of the General Formula (I) where Q 1 is bromine, Q 2 is hydrogen, Q 3 is methyl, n is 0, L is O, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 26 is the same as compound 1 of Table 1 except that in compound 1 of Table 26 R1 is ethyl, Q1 is bromine, Q2 is hydrogen, Q3 is methyl . Similarly, compounds 2 to 323 of Table 26 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 26 R1 is ethyl, Q1 is bromine, Q2 is hydrogen, Q3 is methyl.
Table 27 The compounds of Table 27 are of the Formula General (I) where Q 1 is iodine, Q 2 is hydrogen, Q 3 is methyl, n is 0, L is O, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of the Table 27 is the same as compound 1 of Table 1 except that in compound 1 of Table 27 R 1 is ethyl, Q 1 is iodine, Q 2 is hydrogen, Q 3 is methyl. Similarly, compounds 2 to 323 of Table 27 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 27 R 1 is ethyl, Q 1 is iodine, Q 2 is hydrogen, Q3 is methyl.
Table 28 The compounds of Table 28 are of the General Formula (I) where Q 1 is hydrogen, Q 2 is hydrogen, Q 3 is methyl, n is 0, L is O, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 28 is the same as compound 1 of Table 1 except that in compound 1 of Table 28 R1 is ethyl, Q1 is hydrogen, Q2 is hydrogen, Q3 is methyl . Similarly, compounds 2 to 323 of Table 28 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 28 R1 is ethyl, Q1 is hydrogen, Q2 is hydrogen, Q3 is methyl.
Table 29 The compounds of Table 29 are of the Formula General (I) where Q 1 is thiophen-3-yl, Q 2 is hydrogen, Q 3 is chlorine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, the Compound 1 of Table 29 is the same as Compound 1 of Table 1 except that in Compound 1 of Table 29 Q1 is thiophen-3-yl, Q2 is hydrogen, Q3 is chloro. Similarly, compounds 2 to 323 of Table 29 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 29 Q1 is thiophen-3-yl, Q2 is hydrogen, Q3 is chlorine.
Table 30 The compounds of Table 30 are of the General Formula (I) where Q 1 is thiophen-3-yl, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is 0, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 30 is the same as compound 1 of Table 1 except that in compound 1 of Table 30 Q1 is thiophen-3-yl, Q2 is hydrogen , Q3 is fluoro. Similarly, compounds 2 to 323 of Table 30 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 30 Q1 is thiophen-3-yl, Q2 is hydrogen, Q3 is fluoro.
Table 31 The compounds of Table 31 are of the Formula General (I) where Q 1 is thiophen-2-yl, Q 2 is hydrogen, Q 3 is chlorine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, the Compound 1 of Table 31 is the same as Compound 1 of Table 1 except that in Compound 1 of Table 31 Q1 is thiophen-2-yl, Q2 is hydrogen, Q3 is chloro. Similarly, compounds 2 to 323 of Table 31 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 31 Q1 is thiophen-2-yl, Q2 is hydrogen, Q3 is chlorine.
Table 32 The compounds of Table 32 are of the General Formula (I) where Q 1 is thiophen-2-yl, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 32 is the same as compound 1 of Table 1 except that in compound 1 of Table 32 Q1 is thiophen-2-yl, Q2 is hydrogen , Q3 is fluoro. Similarly, compounds 2 to 323 of Table 32 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 32 Q1 is thiophen-2-yl, Q2 is hydrogen, Q3 is fluoro.
Table 33 The compounds of Table 33 are of the Formula General (I) where Q 1 is thiophen-3-yl, Q 2 is hydrogen, Q 3 is chlorine, n is 0, L is O, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, the Compound 1 of Table 33 is the same as Compound 1 of Table 1 except that in Compound 1 of Table 33 Q1 is thiophen-3-yl, Q2 is hydrogen, Q3 is chloro. Similarly, compounds 2 to 323 of Table 33 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 33 Q1 is thiophen-3-yl, Q2 is hydrogen, Q3 is chlorine.
Table 34 The compounds of Table 34 are of the General Formula (I) where Q 1 is thiophen-3-yl, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is 0, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 34 is the same as compound 1 of Table 1 except that in compound 1 of Table 34 Ql is thiophen-3-yl, Q2 is hydrogen , Q3 is fluoro. Similarly, compounds 2 to 323 of Table 34 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 34 Q1 is thiophen-3-yl, Q2 is hydrogen, Q3 is fluoro.
Table 35 The compounds of Table 35 are of the Formula General (I) where Q 1 is thiophen-2-yl, Q 2 is hydrogen, Q 3 is chlorine, n is 0, L is 0, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, the Compound 1 of Table 35 is the same as Compound 1 of Table 1 except that in Compound 1 of Table 35 Q1 is thiophen-2-yl, Q2 is hydrogen, Q3 is chloro. Similarly, compounds 2 to 323 of Table 35 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 35 Q1 is thiophen-2-yl, Q2 is hydrogen, Q3 is chlorine.
Table 36 The compounds of Table 36 are of the General Formula (I) where Q 1 is thiophen-2-yl, Q 2 is hydrogen, Q 3 is fluoro, n is 0, L is O, R 1 is ethyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 36 is the same as compound 1 of Table 1 except that in compound 1 of Table 36 Ql is thiophen-2-yl, Q2 is hydrogen , Q3 is fluoro. Similarly, compounds 2 to 323 of Table 36 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 36 Q1 is thiophen-2-yl, Q2 is hydrogen, Q3 is fluoro.
Table 37 The compounds of Table 37 are of the Formula General (I) where Ql is chlorine, Q2 is methyl, Q3 is chlorine, n is 0, L is O, R1 is methyl, R2 and R3 have the values listed in Table 1. Therefore, compound 1 of the Table 37 is the same as compound 1 of Table 1 except that in compound 1 of Table 37 Ql is chlorine, Q2 is methyl, Q3 is chlorine. Similarly, compounds 2 to 323 of Table 37 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 37 Ql is chlorine, Q2 is methyl, Q3 is chlorine.
Table 38 The compounds of Table 38 are of the General Formula (I) where Q 1 is bromine, Q 2 is methyl, Q 3 is chlorine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 38 is the same as compound 1 of Table 1 except that in compound 1 of Table 38 Ql is bromine, Q2 is methyl, Q3 is chlorine. Similarly, compounds 2 to 323 of Table 38 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 38 Ql is bromine, Q2 is methyl, Q3 is chlorine.
Table 39 The compounds of Table 39 are of the Formula General (I) where Q 1 is iodine, Q 2 is methyl, Q 3 is chlorine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of the Table 39 is the same as compound 1 of Table 1 except that in compound 1 of Table 39 Ql is iodine, Q2 is methyl, Q3 is chlorine. Similarly, compounds 2 to 323 of Table 39 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 39 Ql is iodine, Q2 is methyl, Q3 is chlorine.
Table 40 The compounds of Table 40 are of the General Formula (I) where Q 1 is fluoro, Q 2 is methyl, Q 3 is chlorine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 40 is the same as compound 1 of Table 1 except that in compound 1 of Table 40 Q1 is fluoro, Q2 is methyl, Q3 is chloro. Similarly, compounds 2 to 323 of Table 40 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 40 Q1 is fluoro, Q2 is methyl, Q3 is chloro.
Table 41 The compounds of Table 41 are of the General Formula (I) where Q 1 is chlorine, Q 2 is methyl, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 41 is the same as compound 1 of Table 1 except that in compound 1 of Table 41 Ql is chlorine, Q2 is methyl, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 41 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 41 Ql is chlorine, Q2 is methyl, Q3 is fluoro.
Table 42 The compounds of Table 42 are of the General Formula (I) where Q 1 is bromine, Q 2 is methyl, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 42 is the same as compound 1 of Table 1 except that in compound 1 of Table 42 Q1 is bromine, Q2 is methyl, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 42 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 42 Q1 is bromine, Q2 is methyl, Q3 is fluoro.
Table 43 The compounds of Table 43 are of the General Formula (I) where Q 1 is iodine, Q 2 is methyl, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 43 is the same as compound 1 of Table 1 except that in compound 1 of Table 43 Ql is iodine, Q2 is methyl, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 43 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 43 Q1 is iodine, Q2 is methyl, Q3 is fluoro.
Table 44 The compounds of Table 44 are of the General Formula (I) where Q 1 is fluoro, Q 2 is methyl, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 44 is the same as compound 1 of Table 1 except that in compound 1 of Table 44 Q1 is fluoro, Q2 is methyl, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 44 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 44 Q1 is fluoro, Q2 is methyl, Q3 is fluoro.
Table 45 The compounds of Table 45 are of the General Formula (I) where Q 1 is chlorine, Q 2 is methyl, Q 3 is bromine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 45 is the same as compound 1 of Table 1 except that in compound 1 of Table 45 Ql is chlorine, Q2 is methyl, Q3 is bromine. Similarly, compounds 2 to 323 of Table 45 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 45 Ql is chlorine, Q2 is methyl, Q3 is bromine.
Table 46 The compounds of Table 46 are of the General Formula (I) where Q 1 is bromine, Q 2 is methyl, Q 3 is bromine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 46 is the same as compound 1 of Table 1 except that in compound 1 of Table 46 Ql is bromine, Q2 is methyl, Q3 is bromine. Similarly, compounds 2 to 323 of Table 46 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 46 Q1 is bromine, Q2 is methyl, Q3 is bromine.
Table 47 The compounds of Table 47 are of the General Formula (I) where Q 1 is iodine, Q 2 is methyl, Q 3 is bromine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 47 is the same as compound 1 of Table 1 except that in compound 1 of Table 47 Ql is iodine, Q2 is methyl, Q3 is bromine. Similarly, compounds 2 to 323 of Table 47 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 47 Ql is iodine, Q2 is methyl, Q3 is bromine.
Table 48 The compounds of Table 48 are of the General Formula (I) where Q 1 is fluoro, Q 2 is methyl, Q 3 is bromine, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 48 is the same as compound 1 of Table 1 except that in compound 1 of Table 48 Q1 is fluoro, Q2 is methyl, Q3 is bromine. Similarly, compounds 2 to 323 of Table 48 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 48 Q1 is fluoro, Q2 is methyl, Q3 is bromine.
Table 49 The compounds of Table 49 are of the General Formula (I) where Q 1 is chlorine, Q 2 is chlorine, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 49 is the same as compound 1 of Table 1 except that in compound 1 of Table 49 Ql is chlorine, Q2 is chlorine, Q3 is fluoro. Similarly, compounds 2 through 323 of Table 49 are the same as compounds 2 through 323 of Table 1, respectively, except that in the compounds of Table 49 Q 1 is Q 1 is chlorine, Q 2 is chlorine, Q 3 is fluoro.
Table 50 The compounds of Table 50 are of the General Formula (I) where Q 1 is bromine, Q 2 is chlorine, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 50 is the same as compound 1 of Table 1 except that in compound 1 of Table 50 Q1 is bromine, Q2 is chlorine, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 50 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 50 Q1 is Q1 is bromine, Q2 is chlorine, Q3 is fluoro.
Table 51 The compounds of Table 51 are of the General Formula (I) where Q 1 is fluoro, Q 2 is chloro, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 51 is the same as compound 1 of Table 1 except that in compound 1 of Table 51 Ql is fluoro, Q2 is chloro, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 51 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 51 Q1 is Q1 is fluoro, Q2 is chloro, Q3 is fluoro.
Table 52 The compounds of Table 52 are of the General Formula (I) where Q 1 is iodine, Q 2 is chlorine, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 52 is the same as compound 1 of Table 1 except that in 'compound 1 of Table 52 Ql is iodine, Q2 is chlorine, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 52 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 52 Q1 is Q1 is iodine, Q2 is chlorine, Q3 is fluoro.
Table 53 The compounds of Table 53 are of the General Formula (I) where Q 1 is chlorine, Q 2 is bromine, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 53 is the same as compound 1 of Table 1 except that in compound 1 of Table 53 Ql is chlorine, Q2 is bromine, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 53 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 53 Q1 is Q1 is chlorine, Q2 is bromine, Q3 is fluoro.
Table 54 The compounds of Table 54 are of the General Formula (I) where Q 1 is bromine, Q 2 is bromine, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 54 is the same as compound 1 of Table 1 except that in compound 1 of Table 54 Ql is bromine, Q2 is bromine, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 54 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 54 Q1 is Q1 is bromine, Q2 is bromine, Q3 is fluoro.
Table 55 The compounds of Table 55 are of the General Formula (I) where Q 1 is fluoro, Q 2 is bromine, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 55 is the same as compound 1 of Table 1 except that in compound 1 of Table 55 Q1 is fluoro, Q2 is bromine, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 55 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 55 Q1 is Q1 is fluoro, Q2 is bromine, Q3 is fluoro.
Table 56 The compounds of Table 56 are of the Formula General (I) where Q1 is iodine, Q2 is bromine, Q3 is fluoro, n is 0, L is O, R1 is methyl, R2 and R3 have the values listed in Table 1. Therefore, compound 1 of the Table 56 is the same as compound 1 of Table 1 except that in compound 1 of Table 56 Ql is iodine, Q2 is bromine, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 56 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 56 Q1 is Q1 is iodine, Q2 is bromine, Q3 is fluoro.
Table 57 The compounds of Table 57 are of the General Formula (I) where Q 1 is chlorine, Q 2 is fluoro, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 57 is the same as compound 1 of Table 1 except that in compound 1 of Table 57 Ql is chlorine, Q2 is fluoro, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 57 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of the Table 57 Ql is Ql is chlorine, Q2 is fluoro, Q3 is fluoro.
Table 58 The compounds of Table 58 are of the General Formula (I) where Q 1 is bromine, Q 2 is fluoro, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 58 is the same as compound 1 of Table 1 except that in compound 1 of Table 58 Ql is bromine, Q2 is fluoro, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 58 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 58 Q1 is Q1 is bromine, Q2 is fluoro, Q3 is fluoro.
Table 59 The compounds of Table 59 are of the General Formula (I) where Q 1 is fluoro, Q 2 is fluoro, Q 3 is fluoro, n is 0, L is 0, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 59 is the same as compound 1 of Table 1 except that in compound 1 of Table 59 Q1 is fluoro, Q2 is fluoro, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 59 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 59 Q1 is Q1 is fluoro, Q2 is fluoro, Q3 is fluoro.
Table 60 The compounds of Table 60 are of the General Formula (I) where Q 1 is iodine, Q 2 is fluoro, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 have the values listed in Table 1. Therefore, compound 1 of Table 60 is the same as compound 1 of Table 1 except that in compound 1 of Table 60 Ql is iodine, Q2 is fluoro, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 60 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 60 Q1 is Q1 is iodine, Q2 is fluoro, Q3 is fluoro.
Table 61 The compounds of Table 61 are of the General Formula (I) where Q 1 is thiof en- 3 -i 1, Q 2 is fluoro, Q 3 is fluoro, n is 0, L is O, R 1 is methyl, R 2 and R 3 they have the values listed in Table 1. Therefore, compound 1 of Table 61 is the same as compound 1 of Table 1 except that in compound 1 of Table 61 Ql is thiof en- 3 - i 1 or, Q2 is fluoro, Q3 is fluoro. Similarly, compounds 2 to 323 of Table 61 are the same as compounds 2 to 323 of Table 1, respectively, except that in the compounds of Table 61 Q1 is Q1 is thiophen-3-yl, Q2 is fluoro, Q3 is fluoro.
Tables 62 to 121 Tables 62 to 121 correspond exactly to the Tables 1 to 61 (that is, Table 62 corresponds exactly to Table 1, Table 63 corresponds exactly to Table 2, and so on) with the only difference that in each of Tables 62 to 121, L is S instead of 0.
Tables 122 to 181 Tables 122 to 181 correspond exactly to Tables 1 to 61 (ie Table 122 corresponds exactly to Table 1, Table 123 corresponds exactly to Table 2, and so on) with the only difference being that in each of Tables 122 through 181, n is 1 instead of 0.
Tables 182 to 241 Tables 182 to 241 correspond exactly to Tables 1 to 61 (ie Table 182 corresponds exactly to Table 1, Table 183 corresponds exactly to Table 2, and so on) with the only difference being that in each of Tables 182 to 241, n is 2 instead of 0. The compounds of the General Formula (I) can be prepared as indicated in Reaction Schemes 1 to 8 to then, in which Q1, Q2, Q3, R1, R2 and R3 have the meanings given above, R14 is H or alkyl (Ci-4), as indicated, R10 is alkyl (Ci-6), optionally substituted benzyl, optionally substituted (C 2-6) alkenyl, (C 2-4) alkynyl optionally substituted, R 6, R 7, R 8, R 9, R 12 and R 13 are independently H or (C 1-4) alkyl, R 9 is H or (1-3C) alkyl , Rh is H or (1-3C) alkyl, R 1 is (Ci-6) alkyl, optionally substituted benzyl, optionally substituted (C 2-6) alkenyl, (C2-4) alkynyl optionally substituted, m is 0, 1 or 2, D F is?,? - dimethylformamide, NBS is N-bromosuccinimide, NCS is N-chlorosuccinimide and MCPBA is m-chloroperbenzoic acid. Other abbreviations are defined in the text. When typical or preferred process conditions are indicated (reaction temperature, time, solvent, molar ratios of reagents), unless otherwise specified, other process conditions may also be used. Although the optimum reaction conditions may vary according to the reagents or solvents used in particular, those skilled in the art can determine these conditions by routine optimization procedures. The compounds of formula (1), wherein n is 0 and L is O, can be prepared as shown in Reaction Scheme 1. The esters of formula (2), wherein R5 is (C -4) alkyl, can be halogenated to obtaining haloesters of formula (3), wherein Hal is a halogen atom such as bromine, chlorine or iodine, by reaction with a halogenating agent such as N- bromosuccinimide, in a suitable solvent such as carbon tetrachloride or acetonitrile, in the presence of a radical initiator such as AIBN (azo-isobutyronitrile), and a light source, at between room temperature and the reflux temperature of the solvent. The compounds of the general formula (3) are then reacted with alkanethiols of the general formula ^ SH, in the presence of a base such as sodium hydride, in a suitable solvent such as DMF, to obtain compounds of the general formula (6), or they are reacted with alkyllithiol salts of M +, where M is a metal such as sodium or lithium, in a suitable solvent such as DMF, to obtain compounds of General Formula (6).
Alternatively, esters of General Formula (4) are halogenated to obtain haloesters of formula (5), where Hal is a halogen atom such as bromine, chlorine or iodine, by reaction with a halogenating agent such as N-chlorosuccinimide or N-bromosuccinimide, in a suitable solvent such as carbon tetrachloride or acetonitrile, at between 0 ° C and the reflux temperature of the solvent. The haloesters of formula (5) are reacted with 6-hydroxy quinolines, where Q 1, Q 2 and Q 3 are as defined above, in the presence of a base such as potassium t-butoxide, potassium carbonate, or sodium hydride in a suitable solvent such as t-butanol, 1,4-dioxane or DMF, at between room temperature and the reflux temperature of the solvent, to obtain compounds of formula (6). The compounds of formula (6) are hydrolyzed to acids of formula (7) by reaction with an alkali metal hydroxide M + 0H ~, in a suitable solvent such as aqueous methanol, ethanol, or THF (tetrahydrofuran) at between room temperature and the reflux temperature of the solvent followed by acidification. The acids of formula (7) can be condensed with amines of formula (8), employing suitable activating agents such as HOBT (1-hydroxybenzotriazole) and EDC (1-ethyl-3-? -dimethylaminopropylcarbodiimide hydrochloride), among 0 ° C and room temperature in a suitable solvent such as DMF, to obtain compounds of General Formula (1) where n is 0 and L is O. Compounds of General Formula (1), where n is 1 or 2, are prepared by oxidation of compounds (1) where n = 0 to the oxidation state of the sulfoxide (n is 1) or sulfone (n is 2), as shown in Reaction Scheme 2. For example, the esters of the General Formula (6) wherein R5 is (C1-4) alkyl they can be oxidized to sulfoxides of formula (9) with an oxidizing agent such as sodium periodate in a suitable solvent such as ethanol, between 0 ° C and room temperature. The sulfones of formula (10) can be prepared directly from compounds of formula (6) with two or more equivalents of an oxidizing agent such as m-chloroperbenzoic acid (MCPBA), in a suitable solvent such as dichloromethane between 0 ° C. and the reflux temperature of the solvent, or from sulfoxides of formula (9) with one or more equivalents of m-chloroperbenzoic acid. The sulfides of formula (6), sulfoxides of formula (9) or sulfones of formula (10) can be hydrolysed to the corresponding acids (7), (11) or (12) by reaction with an alkali metal hydroxide in a suitable solvent such as ethanol at 0 ° C and the reflux temperature of the solvent followed by acidification. The acids of formula (7), (11) or (12) can be condensed with amines of formula (8), using suitable activating agents such as HOBT and EDC, at between 0 ° C and room temperature, to obtain compounds of Formula General (1) where n is 0, 1 or 2. reaction scheme 2 eg MCPBA Similarly, the sulfoxides of formula (11) and of formula (1) wherein n is 1 can be prepared from the sulfides of formula (7) and of formula (1) where n is 0 respectively, employing oxidizing agents such as sodium metaperiodate or m-chloroperbenzoic acid as described above. The sulfones of formula (12) and of formula (1) wherein n is 2, can be prepared from the sulfides of formula (7) and of formula (1) where n is 0, employing at least two equivalents of oxidizing agents such as m-chloroperbenzoic acid, or from sulfoxides of formula (11) and of formula (1) where n is 1, employing one or more equivalents of oxidizing agents such as m-chloroperbenzoic acid, as described above. The compounds of formula (1) can also be prepared as shown in Reaction Scheme 3. Acids of formula (13) can be condensed with amines of formula (8), by suitable activating agents such as HOBT and EDC, a 0 ° C and room temperature, to obtain compounds of formula (14). The compounds of formula (14) can be halogenated to compounds of formula (16) by employing a halogenating agent such as N-chlorosuccinimide, in a suitable solvent such as carbon tetrachloride or acetonitrile, at between 0 ° C and room temperature. Amides of formula (16) can also be prepared from acid halides of formula (15) by reaction with amines of formula (8) in the presence of a base such as triethylamine in a suitable solvent such as dichloromethane, at 0 ° C. and room temperature.
Reaction scheme 3 (16) (1) where n = 0 The halosulfides of formula (16) can be reacted with substituted 6-hydroxy quinolines, in the presence of a base such as potassium carbonate or sodium hydride, in a suitable solvent such as DMF, at 0 ° C to 80 ° C, to obtain compounds of formula (1) wherein n is 0. As shown in Reaction Scheme 4, the amines of the General Formula (18) or (20), which are examples of amines of the General Formula (8) where R2 is H, they can be prepared by alkylation of an aminoalcohol of the General Formula (17) or (19) using a suitable base, such as n-butyl lithium or sodium hydride, followed by reaction with a suitable alkylating reagent R10LG, such as an alkyl iodide, for example, methyl iodide, to form an alkylated compound of the General Formula (18) or (20), respectively. A carbonyl derivative R12COR13 (21), for example formaldehyde, can be reacted with ammonia, generally in the form of ammonium chloride, and cyanide, conveniently in the form of an aqueous solution of sodium cyanide, to obtain an a-aminoalkyne ( 22) (Synthesis of Strecker).
Reaction scheme 4 (17) (18) As shown in Reaction Scheme 5, the silyl-protected aminoalkynes of the General Formula (24) can be obtained by reacting amines of General Formula (23) with 1,2-bis- (chlorodimethylsilyl) ethane in the presence of a suitable base , such as a tertiary organic amine base, for example, triethylamine. The amines of the General Formula (26), which are examples of amines of the General Formula (8) wherein R2 is H and R3 is - (CR30R40) C = CR50, can be prepared by alkylation of a silyl-protected aminoalkyne of the Formula General (24) using a suitable base, such as n-butyl lithium, followed by reaction with a suitable alkylating reagent R50LG, such as an alkyl iodide, for example, methyl iodide, to form an alkylated compound of the General Formula ( 25). The silyl protecting group can then be removed from a compound of the General Formula (25) with, for example, a aqueous to form an aminoalkyne of the General Formula In a similar procedure, a silyl-protected aminoalkyne of the General Formula (24) can be reacted with a carbonyl derivative RaCORb, for example formaldehyde, using a suitable base, such as n-butyl lithium, to obtain an aminoalkino (27). ) containing a hydroxyalkyl moiety. A compound of the General Formula (27) can be treated first with a base, such as sodium hydride or potassium bis (trimethylsilyl) amide and then with a compound RCLG, where LG represents a leaving group such as a halogen, or ester of sulfonate such as 0S02Me, or OSC > 2-4-tolyl, for example ethyl iodide, to obtain a composed of the General Formula (29). After removing the silyl protecting group, the compounds of General Formula (30) are obtained. Alternatively, the silyl protecting group can be removed first to obtain compounds of the General Formula (28). The aminoalkynes of the General Formula (28) can be further derivatized by reacting them with a silylating agent, for example t-butyldimethylsilyl chloride, to obtain a silylated derivative in the oxygen of the General Formula (31).h.
Reaction scheme 6 As shown in Reaction Scheme 6, the silyl-protected aminoalkynes of the General Formula (32) can be obtained by reacting silyl-protected amines of General Formula (24) with chloroalkanes bearing a suitable leaving group, for example bromide or iodide, in the presence of a suitable base, such as a sodium or lithium amide base, for example, sodium bis (trimethylsilyl) amide or sodium amide. The amines of the General Formula (34), which are examples of amines of the General Formula (8) where R2 is H and R3 is - (CR30R40) C = CR50 can be prepared by displacement of a chloride anion by the cyanide, and then removal of the silyl protecting group with, for example, an aqueous acid, to form a cyano compound of the General Formula (34). In a similar procedure, an amide of the General Formula (35) can be reacted with, for example, potassium cyanide to obtain a cyano amidoalkyne of the General Formula (36). As shown in Reaction Scheme 7, the compounds of the General Formula (1), wherein R50 is H, can react under Sonogashira conditions with, for example, optionally substituted aryl or heteroaryl chlorides, bromides, iodides or triflates. to form substituted aryl or heteroaryl compounds of General Formula (1), wherein R50 is an optionally substituted aryl or heteroaryl group. A suitable palladium catalyst is bis (triphenylphosphine) palladium (II) chloride.
(Hetero) aryl (1) where R2 = H and palladium R3 is - (CRSOR'IOJCCRSO, R50 = H) L = Cl, Br. I. OS02CF3 Other amines of the General Formula (8) are available commercially or can be prepared by standard methods found in the literature or standard modifications. As shown in Reaction Scheme 8, compounds of the General Formula (1), where Q 1 is bromine or iodine, can react under Suzuki conditions with, for example, aryl or heteroaryl boronic acids optionally substituted to form aryl compounds or substituted heteroaryls of General Formula (1), wherein Q 1 is an optionally substituted aryl or heteroaryl group. A suitable palladium catalyst is tetrakis (triphenylphosphine) palladium (0). (1) where Q 1 = Br, I, n = 1 Thioamides (Compounds of the General Formula (1) where L = S) can be prepared from the corresponding amides using thionation agents such as phosphorus pentasulfide, Lawesson's or Davy's reagents or prepared from the corresponding thionoacids or thionosters by standard methods found in the literature or standard modifications. Substituted 6-hydroxy quinolines are achieved, or can be prepared by elementary techniques of organic chemistry. When the compounds are not commercially available, they can be prepared from available precursors by elementary transformations which are well known in the art and which are well described in the usual texts of heterocyclic chemistry. For example, the substituted aromatic amines can be easily converted to substituted quinolin-6-ols with appropriate electrophiles, such as 2,2,3-tribromopropanal. In the Examples 1 to 3 are examples of such reactions. The compounds of formula (I) are active fungicides and can be used to control one or more of the following pathogens: Pyricularia oryzae (Magnaporthe grisea) from rice and wheat and other Pyricularia spp. from other hosts; Puccinia triticina (or recondite), Puccinia striiformis and other blights of wheat, Puccinia hordei, Puccinia striiformis and other blights of barley, and blights of other hosts (eg turf, rye, coffee, pears, apples, peanuts, sugar beet, ornamental plants and plants); Erysiphe cichoracearum of cucurbits (for example melon); Blumeria (or Erysiphe) graminis (powdery mildew) of barley, wheat, rye and turf and other types of powdery mildew of various hosts, such as Sphaerotheca macularis of hops, Sphaerotheca fusca (Sphaerotheca fuliginea) of cucurbits (eg cucumber) , Leveillula taurica of tomatoes, aubergines and green peppers, Podosphaera leucotricha of apples and Uncinula necator of the vines; Cochliobolus spp., Helminthosporium spp., Drechslera spp. (Pyrenophora spp.), Rhynchosporium spp., Ycosphaerella graminicola (Septoria tritici) and Phaeosphaeria nodorum (Stagonospora nodorum or Septoria nodorum), Pseudocercosporella herpotrichoides and Gaeumannomyces graminis of cereals (for example wheat, barley, rye), turf and other hosts; Cercospora arachidicola and Cercosporidium personatum from peanuts and other Cercospora spp. from other hosts, for example, sugar beet, bananas, soybeans and rice; Botrytis cinerea (gray mold) of tomatoes, strawberries, vegetables, vines and other hosts and other Botrytis spp. from other hosts; I would alternate spp. of vegetables (eg carrots), oilseed rape, apples, tomatoes, potatoes, cereals (eg wheat) and other hosts; Venturia spp. (including Venturia inaequalis (escabro)) of apples, pears, stone fruits, nuts and other hosts; Cladosporium spp. from a variety of hosts including cereals (eg wheat) and tomatoes; Monilinia spp. of stone fruits, nuts and other hosts; Didymella spp. of tomatoes, turf, wheat, cucurbits and other hosts; Phoma spp. of oilseed rape, turf, rice, potatoes, wheat and other hosts; Aspergillus spp. and Aureobasidium spp. of wheat, wood and other hosts; Ascochyta spp. of peas, wheat, barley and other hosts; Stemphylium spp. (Pleospora spp.) Of apples, pears, onions and other hosts; summer diseases (eg bitter rot (Glomerella cingulata), black rot or leaf spot frog's eye (Botryosphaeria obtusa), points of Brook fruit (Mycosphaerella pomi), blight of cedar apple (Gymnosporangium j uniperi-virginianae), disease of soot (Gloeodes pomigena), fly feces (Schizothyrium pomi) and white rot (Botryosphaeria dothidea)) of apples and pears; Plasmopara viticulture of the vines; other types of downy mildew, such as Bremia lactucae of lettuce, Peronospora spp. of soybeans, tobacco, onions and other hosts, Pseudoperonospora humuli of hops and Pseudoperonospora cubensis of cucurbits; Pythium spp. (including Pythium ultimum) of turf and other hosts; Phytophthora infestans of potatoes and tomatoes and other Phytophthora spp. of vegetables, strawberries, avocados, peppers, ornamental plants, tobacco, cocoa and others hosts; Thanatephorus cucumeris of rice and turf and other Rhizoctonia spp. from various hosts such as wheat and barley, peanuts, vegetables, cotton and turf; Sclerotinia spp. of grass, peanuts, potatoes, oilseed rape and other hosts; Sclerotium spp. of grass, peanuts and other hosts; Gibberella fujikuroi of rice; Colletotrichum spp. from a variety of hosts including grass, coffee and vegetables; Laetica fuciformis of the lawn; Mycosphaerella spp. of bananas, peanuts, citrus fruits, pecans, papaya and other hosts; Diaporthe spp. of citrus fruits, soybeans, melons, pears, lupins and other hosts; Elsinoe spp. of citrus fruits, vines, olives, pecans, roses and other hosts; Verticillium spp. from a variety of hosts including hops, potatoes and tomatoes; Pyrenopeziza spp. of oilseed rape and other hosts; Oncobasidium theobromae of cocoa that causes vascular streak dieback ("vascular streak dieback"); Fusarium spp., Typhula spp., Microdochium nivale, Ustilago spp., Urocystis spp., Tilletia spp. and Claviceps purpurea from a variety of hosts but especially wheat, barley, turf and corn; Ramularia spp. of sugar beet, barley and other hosts; postharvest diseases especially of fruit (for example Penicillium digitatum, Penicillium italicum and Trichoderma viride of oranges, Colletotrichum musae and Gloeosporium musarum of bananas and Botrytis cinerea of grapes); other pathogens the vines, particularly Eutypa lata, Guignardia bidwellii, Phellinus igniarus, Phomopsis viticola, Pseudopeziza tracheiphila and Stereum hirsutum; other tree pathogens (for example Lophodermium seditiosum) or wood, particularly Cephaloascus fragrans, Ceratocystis spp., Ophiostoma piceae, Penicillium spp., Trichoderma pseudokoningii, Trichoderma viride, Trichoderma harzianum, Aspergillus niger, Leptographium lindbergi and Aureobasidium pullulans; and fungal vectors of viral diseases (for example Polymyxa graminis of cereals as the vector of yellow mosaic virus of barley (BYMV) and Polymyxa betae of sugar beet as the vector of rhizomania). A compound of formula (I) can move acropionately, basileptically or locally in plant tissue to be active against one or more fungi. In addition, a compound of Formula (I) may be sufficiently volatile to be active in the vapor phase against one or more fungi of the plant. The invention therefore proposes a method for combating or controlling phytopathogenic fungi which comprises applying an effective amount as a fungicide of a compound of Formula (I), or a composition containing a compound of Formula (I), to a plant, a seed of a plant, to the locus of the plant or seed or to the soil or any other means for the development of a plant, p. e. nutrient solution.
The term "plant" in the context of the present includes buds, shrubs and trees. In addition, the fungicidal method of the invention includes protective, curative, systemic, eradicating and antisporulating treatments. The compounds of formula (I) are preferably used in the agricultural, horticultural and turf care fields in the form of a composition. To apply a compound of formula (I) to a plant, to a seed of a plant, to the locus of the plant or seed or to the soil or any other means for its development, a compound of formula (I) is formulated in general as a composition that includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surfactant (SFA). SFAs are chemical products capable of modifying the properties of an inferium (for example, liquid / solid, liquid / gas or liquid / liquid interfaces) by decreasing the interfacial tension and through this changes are achieved in other properties (for example dispersion, emulsion and wetting). It is desirable that all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of a compound of formula (I). The composition is generally used to control fungi such that a compound of formula (I) is applied at an average of from O.lg to 10 kg. per hectare, preferably from 1 g to 6 kg per hectare, more preferably from lg to 1 kg per hectare. When used as a seed coat, a compound of formula (I) is applied at an average of 0.0001 g to 10 g (eg 0.001 g or 0.05 g), preferably 0.005 g to 10 g, more preferably 0.005 g to 4 g, per kilogram of seed. In another aspect, the present invention proposes a fungicidal composition comprising an effective fungicidal amount of a compound of formula (I) and a diluent or carrier suitable therefor. In another of the aspects, the invention proposes a method for combating and controlling fungi in a locus, which consists in treating the fungi, or the locus of the fungi with an effective amount as a fungicide of a composition comprising a compound of formula (I). ). The compositions can be selected from a variety of formulation types, including spreading powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), hydratable powders (WP), granules ( GR) (slow release or rapid release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) as water in oil (EO)), micro- emulsions (ME), suspension concentrates (SC), aerosols, vapor / smoke formulations, encapsulated suspensions (CS) and formulations for the treatment of seeds. The type of formulation chosen will depend, in any case, on the particular purpose assigned to it and on the physical, chemical and biological properties of the compound of formula (I). The spreading powders (DP) can be prepared by mixing a compound of formula (I) with one or more solid diluents (eg natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earth, calcium phosphates , calcium and magnesium carbonates, sulfur, lime, flours, talc and other solid organic and inorganic carriers) and mechanically grinding the mixture to a fine powder. Soluble powders (SP) can be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids ( such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of the agents to improve dispersibility / solubility in water. The mixture is then ground to a fine powder. Similar compositions can also be prepared in granules to form water soluble granules (SG).
Hydratable powders (WP) can be prepared by mixing a compound of formula (I) with one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more agents of suspension to facilitate dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions can also be prepared in granules to form water dispersible granules (WG). Granules (GR) can be formed by granulating a mixture of a compound of formula (I) and one or more solid diluents or powder carriers, or from preformed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice stone, attapulgite clays, fuller earth, kieselguhr, diatomaceous earths or ground corn kernels) or adsorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a hard nuclear material (such as sands, silicates, carbonates, sulphates or mineral phosphates) and drying it if necessary. Agents that are commonly employed to promote absorption or adsorption comprise solvents (such as alcohols, ethers, ketones, esters and aliphatic and aromatic petroleum solvents) and binding agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives can also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent). Dispersible concentrates (DC) can be prepared by dissolving a compound of formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surfactant (for example to improve dilution in water or prevent crystallization in a spray container). Emulsifiable concentrates (EC) or oil-in-water (EW) emulsions can be prepared by dissolving a compound of formula (I) in an organic solvent (optionally with one or more wetting agents, one or more emulsifying agents or a mixture of such agents). Organic solvents suitable for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, for example SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone), alcohols (such as alcohol) benzyl, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as Ce-Cιι fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product can spontaneously emulsify when added to water, to produce an emulsion with sufficient stability to allow application in the form of spray by means of appropriate equipment. The preparation of an EW consists of obtaining a compound of formula (I) in the form of liquid (if it is not a liquid at room temperature, it can be melted at a reasonable temperature, generally below 70 ° C) or in solution (dissolving it in a suitable solvent) and then emulsify the resulting liquid or solution in water containing one or more SFA, with high cut, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other suitable organic solvents of low water solubility. Microemulsions (ME) can be prepared by mixing water with a mixture of one or more solvents with one or more SFA, to spontaneously produce a thermodynamically stable isotropic liquid formulation. At the beginning, the compound of formula (I) is present either in the water or in the solvent / SFA mixture. Suitable solvents for use in EMs include those described so far for use in EC or EW. A ME can be an oil-in-water or water-in-oil system (which system is present can be determined by conductivity measurements) and can be suitable for mixing water-soluble pesticides and oil-soluble in the same formulation. An ME serves to dilute in water, whether it remains as a microemulsion or forms a conventional oil-in-water emulsion. The suspension concentrates (SC) can be aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I). The SCs can be prepared by beating with balls or beads the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a suspension in fine particles of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of formula (I) can be dry milled and added to the water, with the agents described so far, to obtain the desired final product. Aerosol formulations comprise a compound of formula (I) and a suitable propulsive agent (for example n-butane). A compound of formula (I) can also be dissolved or dispersed in a suitable medium (for example water or a water-miscible liquid, such as n-propanol) to obtain compositions for use in manual, non-pressurized spray pumps. A compound of formula (I) can be mixed in its dry state with a pyrotechnic mixture to form a suitable composition to generate, in a closed space, a smoke containing the compound. Encapsulated suspensions (CS) can be prepared in a similar manner to the preparation of formulations E but with an additional polymerization step such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated in a polymeric shell and it contains a compound of formula (I) and, optionally, a carrier or diluent therefor. The polymeric shell can be obtained by interfacial polycondensation reaction or by a coacervation process. The compositions can serve for the controlled release of the compound of formula (I) and can be used for the treatment of seeds. A compound of formula (I) can also be formulated in a biodegradable polymer matrix to achieve slow and controlled release of the compound. A composition may include one or more additives to improve the biological performance of the composition (e.g., improve wetting, retention or distribution on the surface, resistance to rain on the treated surfaces, or the absorption or mobility of a compound of formula (I)). These additives may be surfactants, additives in the form of an oil-based spray, for example some mineral oils or natural vegetable oils (such as as soybean oil and rapeseed oil), and mixtures of these with other bio-enhancing adjuvants (ingredients that can help or modify the action of a compound of formula (I)). A compound of formula (I) can also be formulated to be applied in the treatment of a seed, for example as a powder composition, including a powder for the treatment of dry seeds (DS), a water soluble powder (SS) or a water dispersible powder for suspension treatment (WS), or as a liquid composition, including a fluid concentrate (FS), a solution (LS) or a suspension in capsules (CS). The preparation of compositions DS, SS, WS, FS and LS is very similar to that of the compositions DP, SP, WP, SC and DC, respectively, described above. The compositions for treating seeds may include an agent to facilitate the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier). The wetting agents, dispersing agents and emulsifying agents can be SFA of the cationic, anionic, amphoteric or nonionic type. Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts. Suitable anionic SFAs include alkali metal salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (for example sodium lauryl sulfate), salts of sulfonated aromatic compounds (for example sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonate and mixtures of sodium di-isopropyl- and tri-isopropyl-naphthalene sulfonates), sulfates of ether, alcohol ether sulfates (for example sodium laureth-3-sulfate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products of the reaction between one or more fatty alcohols and phosphoric acid (especially mono-esters) or phosphorus pentoxide (especially di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid, on the other hand these products may be ethoxylated), sulfosuccinamates, sulfonates, taurates and lignosulfonates of paraffin or olefin. Suitable SFAs of the amphoteric type include betaines, propionates and glycinates. Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; products of the condensation of the partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example polyethylene glycol fatty acid esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins. Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and dilating clays (such as bentonite or attapulgite). A compound of formula (I) can be delivered through any known means for applying fungicidal compounds. For example, it can be applied, formulated or unformulated, to any part of the plant, including the foliage, stems, branches or roots, to the seed before planting it or to other means in which the plants develop or in which it is grown. they will plant these (such as the soil surrounding the roots, the soil in general, paddy water or hydroponic growing systems), directly or can be sprayed on, sprinkled on, applied by dipping, applied as a cream or paste formulation , apply as vapor or apply by distribution or incorporation of a composition (such as a granular composition or a composition packed in a water soluble pouch) on land or in an aquatic environment. A compound of formula (I) can also be injected into plants or sprayed onto vegetation using electrodynamic spray techniques or other low-level methods. volume, or applied by terrestrial or aerial irrigation systems. Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active, concentrated ingredient which is integrated into the water before use. Often it is necessary that these concentrates, which can be DC, SC, EC, EW, ME, SG, SP, WP, WG and CS, resist storage for prolonged periods and, after that time, are able to withstand the addition of water to form aqueous preparations that remain homogeneous for a sufficient time that allows their application by conventional spray equipment. These aqueous preparations may contain various amounts of a compound of formula (I) (for example 0.0001 to 10%, by weight) according to the purpose for which it is intended for use. A compound of formula (I) can be used in mixtures with fertilizers (for example fertilizers containing nitrogen, potassium or phosphorus). Suitable fertilizer types include fertilizer granules. The mixtures preferably contain up to 25% by weight of the compound of formula (I). The invention, therefore, also proposes a fertilizer composition comprising a fertilizer and a compound of formula (I). The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having similar or complementary fungicidal activity or possessing herbicidal, insecticidal, nematicidal, acaricidal or plant growth regulating activity. If another fungicide is included, the resulting composition may have a broader spectrum of activity or a higher level of intrinsic activity than the compound of formula (I) alone. In addition, the other fungicide can produce a synergistic effect on the fungicidal activity of the compound of formula (I). The compound of formula (I) may be the sole active ingredient of the composition or may be mixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. The additional active ingredient may: provide a composition having a broader spectrum of activity or greater persistence at a locus; synergizing the activity or complementing the activity (for example increasing the speed of the effect or overcoming the repellency) of the compound of formula (I); or help overcome or prevent the development of resistance to individual components. The additional active ingredient in particular it depends on the purpose to which the composition is intended. Examples of fungicidal compounds that can be included in the composition of the invention are AC 382042 (N- (1-cyano-1,2-dimethylpropyl) -2- (2,4-dichlorophenoxy) pro-pionamide), acibenzolar-S-methyl , alanicarb, aldimorf, anilazine, azaconazole, azafenidine, azoxystrobin, benalaxyl, benomyl, bentiavalicarb, biloxazole, bitertanol, blasticidin S, boscalid (new name of nicobifen), bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim hydrochloride, carboxin, carpropamide, carvone, CGA 41396, CGA 41397, chinomethionate, chlorbenzothiazone, chlorothalonil, chlorozolinate, clozilacon, copper-containing compounds such as copper oxychloride, copper oxy-cyclolate, copper sulfate, copper talate, and Bordeaux mixture, ciamidazosulfamide, cysoxamide ( IKF-916), flufenamide, cymoxanil, cyproconazole, cyprodinil, debacarb, 1,1'-di-2-pyridyl disulfide dioxide, diclofluanid, diclocimet, diclomezine, dichloran, dietofencarb, diphenoconazole, difenzoquat, diflumetorim, ti O, O-di-iso-propyl-S-benzyl, dimefluazole, dimetconazole, dimethirimol, dimetomorph, dimoxystrobin, diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride, dodemorf, dodine, doguadine, edifenfos, epoxiconazole, etaboxam , etirimol, (Z) -N-benzyl- ([methyl (methyl-thioethylidenaminooxycarbonyl) amino] thio) -D-alaninate ethyl, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil (AC 382042), fenpiclonil, fenpropidin, fenpropimorf, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorf, fluorimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hydroxyisoxazole, himexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb, isopropanol butyl carbamate , isoprothiolane, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY 248908, mancozeb, maneb, mefenoxam, mepanipyrim, mepronil, metalaxyl, metalaxyl M, metconazole, metiram, metiram-zinc, metominostrobin, metrafenone, MON65500 (N-alil-4 , 5-dimethyl-2-trimethylsilylthiophen-3-carboxamide), myclobutanil, NTN0301, neoasozin, nickel dimethyldithiocarbamate, nitrotal-iso-propyl, nuarimol, ofura ce, organic mercury compounds, oisastrobin, oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencicuron, phenazine oxide, phosphorus acids, phthalide, picoxystrobin, polyoxin D, polyram, probenazole, prochloraz, procyamide, propamocarb , propamocarb hydrochloride, propiconazole, propineb, propionic acid, proquinazid, protioconazole, pyraclostrobin, pyrazophos, pirifenox, pyrimethanil, piroquilon, piroxifur, pyrrolnitrine, quaternary ammonium compounds, quinomethionate, quinoxifen, quintozene, silthiofam (MON 65500), S-imazalil, simeconazole, sipconazole, sodium pentachlorophenate, spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tecnacene, tetraconazole, thiabendazole , tifluzamide, 2- (thiocyanomethylthio) benzothiazole, thiophanate-methyl, thiram, thiadinyl, timibenconazole, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutyl, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin A, vapam , vinclozolin, XRD-563, zineb, ziram, zoxamide and the compounds of the formulas: The compounds of formula (I) can be mixed with soil, peat or other means for rooting for the protection of plants against diseases with onset in the seed, soil or foliage, caused by fungi. Some mixtures may comprise active ingredients that have significantly different physical, chemical or biological properties, so that they do not all easily lend themselves to the same type of conventional formulation. Under these circumstances, other types of formulation. For example, when one active ingredient is a water-insoluble solid and the other is a water-insoluble liquid, it is possible, however, to disperse each of the active ingredients in the same continuous aqueous phase by dispersing the solid active ingredient in the form of suspension (using a preparation analogous to that of a SC) but dispersing the liquid active ingredient in the form of an emulsion (using a preparation analogous to that of an EW). The resulting composition is a formulation in the form of suspoemulsion (SE). The invention is illustrated by the following Examples in which the following abbreviations are used: mi = milliliters p.f. = melting point (uncorrected) g = grams p.e. = boiling point THF = tetrahydrofuran DMSO = dimethylsulfoxide M + = mass ion DMF = N, N-dimethylformamide s = singlet d = doublet HOBT = 1-hydroxybenzotriazole HOAT = 7-aza-l-hydroxybenzotriazole s amp = broad singlet NMR = nuclear magnetic resonance t = triplet HPLC = high performance liquid chromatography c = quartet TLC = thin layer chromatography m = multiplet glc = gas chromatography - liquid ppm = parts per million EDC = l-ethyl-3-? hydrochloride, N- M = dimethylamino propylcarbodiimide molar EXAMPLE 1 This example illustrates the preparation of 2- (3-bromo-7-chloro-quinolin-6-yloxy) -N-tert-buty1-2-methylsulfanyl-acetamide (Compound No. 12 of Table 2) Step 1: Preparation of 3-bromo-7-chloro-quinolin-6-ol Step 1 3-Chloro-4-methoxy aniline (10 g) in acetic acid (100 ml) was treated with 2,2,3-tribromopropanal (18.8 g) and The mixture was stirred at room temperature for 2 hours after which it was diluted with water and extracted with ethyl acetate. The organic phase was washed with 2N NaOH, dried over sodium sulfate, filtered and evaporated under reduced pressure to obtain the desired product, 3-bromo-7-chloro-6-methoxy-quinoline, as a yellow solid. according to chromatography (silica, hexane / ethyl acetate) (M + 274). NMR H1 (CDC13) d ppm: 8.78 (1H, d); 8.21 (1H, d); 8.10 (1H, s); 7.03 (1H, s). Step 2 A mixture of the product from Step 1 (1.4 g) and hydrobromic acid (water solution 48% by weight) (100 ml x2) was brought to reflux for 62 hours. The mixture was cooled to room temperature, diluted with water, treated with sodium carbonate and hydrogen and extracted with ethyl acetate. The extract was dried over magnesium sulfate, filtered and evaporated under reduced pressure to obtain the sought product, 3-bromo-7-chloro-quinolin-6-ol (M + 260). NMR H1 (DMSO) d ppm: 7.34 (1H, s); 7.07 (1H, s); 8.60 (1H, d); 8.73 (1H, d); 11.12 (1H, s). Step 2: Preparation of (3-bromo-7-chloro-quinolin-6-yloxy) -methylsulfanyl-acetic acid methyl ester Step 1 To a stirred solution of methyl (methylthio) acetate (10.8 ml) in dichloromethane (300 ml) ) cooled to -15 ° C sulfuryl chloride (8.1 ml) was added dropwise. The mixture was allowed to warm to room temperature in a space of two hours and then concentrated under reduced pressure to obtain crude methyl chloro-methylsulfanyl-acetic acid methyl ester in the form of a colorless liquid. The product was used in the next step without further purification. NMR H1 (CDC13) d ppm: 2.33 (3H, s); 3.83 (3H, s); 5.49 (1H, s). Step 2 To a stirred solution of 3-bromo-7-chloro-quinolin-6-ol from Step 1, Step 2 (1.1 g) in dry DMF (17 ml) containing anhydrous potassium carbonate (3.1 g) at room temperature. At room temperature, chloro-methylsulfanyl-acetic acid methyl ester (0.79 g) was added dropwise. The mixture was heated for 1 hour at 60-65 ° C, then cooled to room temperature, diluted with water and extracted with ethyl acetate. The extracts were combined, washed with brine, dried on magnesium sulfate, filtered and evaporated under reduced pressure. Purification of the crude material by chromatography (silica, ethyl acetate / hexane 1: 4 by volume) gave the title compound, 3-bromo-7-chloro-quinolin-6-yloxy) -methylsulfanyl-acetic acid methyl ester. (M + 378). NMR H1 (CDC13) d ppm: 2.29 (3H, s); 3.89 (3H, s); 5.74 (1H, s) 7.18 (1H, 8); 8.16 (1H, s); 8.23 (1H, s); 8.82 (1H, s). Step 3: Preparation of acid (3-bromo-7-chloro-quinolin-6-yloxy) -methylsulfanyl-acetic To a stirred solution of the product from Step 2, Step 2 (1.1 g) in ethanol (14 ml) at room temperature. At room temperature, a 2N sodium hydroxide solution in water (2.2 ml) was added. The mixture was stirred at room temperature for 1 hour and then poured into ice water and acidified with 2M hydrochloric acid. The resulting precipitate was filtered from the solution, washed with cold water and dried under vacuum to obtain (3-bromo-7-chloro-quinolin-6-yloxy) -methylsulfanyl-acetic acid (+ 364). NMR H1 (DMSO-d6) d ppm: 2.20 (3H, s); 6.18 (1H, s); 7.57 (1H, s); 8.19 (1H, s); 8.28 (1H, d); 8.88 (1H, d); 13.7 (1H, s amp). Step 4: Preparation of 2- (3-bromo-7-chloro-quinolin-6-yloxy) -N-tert-buty1-2-methylsulfanyl-acetamide The product of the above Step 3, 3-bromo-7-chloro acid -quinolin-6-yloxy) -methylsulfanyl-acetic acid (85 mg) of in Dry N -dimethylformamide (2 ml) was treated with t-butylamine (17 mg), N- (3-dimethylamino-propyl) -N'-ethyl carbodiimide hydrochloride (45 mg), HOAt (32 mg) and triethylamine ( 24 mg) at room temperature with stirring for 3 hours. The mixture was poured into water, extracted with ethyl acetate (three times) and the extracts were combined, washed with saturated aqueous sodium carbonate solution, water (three times) then dried over magnesium sulfate, filtered and they were evaporated under reduced pressure to obtain an oil. The oil was fractionated by chromatography (silica, hexane / ethyl acetate, 3: 1 by volume) to obtain the desired product as a white solid (mp 172-174 ° C, + 419). NMR H1 (CDCl3) d ppm: 1.46 (9H, s); 2.18 (3H, s); 5.63 (1H, s); 6.89 (1H, s amp); 7.28 (1H, s); 7.28 (1H, s); 8.18 (1H, s), 8.27 (1H, d); 8.83 (1H, d). The following amides were prepared using a similar procedure. Compound No. 238 of Table 2: using 1,1-dimethyl-prop-2-inylamine, m.p. 169-171 ° C; NMR H1 (CDC13) d ppm: 1.75 (6H, s); 2.19 (3H, s); 2.41 (1H, s); 5.69 (1H, s); 7.16 (1H, s amp); 7.29 (1H, s); 8.18 (1H, s); 8.27 (1H, d); 8.83 (1H, d). Compound No. 52 of Table 2: using 2-amino-3-methoxy-2-methyl-propionitrile, NMR H1 (CDC13) d ppm: diastereomeric mixture (1/1); 1.82 and 1.84 (3H, 2xs); 2.18 and 2.20 (3H, 2xs); 3.52 and 3.53 (3H, 2xs); 3.64-3.84 (2H, 2xdd); 5.76 and 5. 77 (1H, 2xs); 7.29 and 7.30 (1H, 2xs); 7.59 and 7.61 (1H, 2x amp); 8.18 (1H, s); 8.29 (1H, d); 8.85 (1H, s). Compound No. 244 of Table 2: using 1,1-dimethyl-but-2-inylamine, m.p. 160-162 ° C; NMR H1 (CDC13) d ppm: 1.71 (6H, s); 1.83 (3H, s); 2.19 (3H, s); 5.66 (1H, s); 7.15 (1H, s amp); 7.27 (1H, s); 8.18 (1H, s); 8.27 (1H, d); 8.83 (1H, d). Compound No. 251 of Table 2: using 4-methoxy-1, 1-dimethyl-but-2-inylamine, m.p. 124-125 ° C; NMR H1 (CDC13) d ppm: 1.75 (6H, s); 2.19 (3H, s); 3.39 (3H, s); 4.13 (2H, s); 5.67 (1H, s); 7.17 (1H, s amp); 7.28 (1H, s); 8.18 (1H, s); 8.28 (1H, d); 8.84 (1H, d).
EXAMPLE 2 This example illustrates the preparation of 2- (3-bromo-7-methyl-quinolin-6-yloxy) -N-tert-buty1-2-methylsulfanyl-acetamide (Compound No. 12 of Table 13) Step 1: Preparation of 3-bromo-7-methyl-quinolin-6-ol 4-Amino-2-methyl-phenol (5 g) in acetic acid (60 ml) was treated with 2,2,3-tribromopropanal (11.9 g) and the The mixture was stirred at room temperature for 3 hours after which it was diluted with water and extracted with ethyl acetate. The organic phase was washed with aqueous NH 4 OH, dried over sodium sulfate, filtered and evaporated under reduced pressure to obtain the desired product, 3-bromo-7-methyl-6-quinolin-6-ol which was used as such. in the next step (M + 240), NMR H1 (D SO-d6). d ppm: 2.32 (3H, s); 7.12 (1H, s); 7.75 (1H, s); 8.46 (1H, d); 8.64 (1H, d); 10.35 (1H, s amp). Step 2: Preparation of methyl 3-bromo-7-methyl-quinolinyl-6-oxy-2-methylthioacetate In a procedure similar to that of Step 2, Step 2 of Example 1, 3-bromo-7-methyl was reacted -quinolin-6-ol with methyl 2-bromo-2-methylthioacetate to obtain 3-bromo-7-methyl-quinolinyl-6-oxy-2-methylthio-methyl acetate (M + 358). NMR H1 (CDC13) d ppm: 2.25 (3H, s); 2.50 (3H, s); 3.88 (3H, s); 5.73 (1H, s); 6.99 (1H, s); 7.86 (1H, s); 8.19 (1H, d), 8.76 (1H, d). Step 3: Preparation of (3-bromo-7-methyl-quinolin-6-yloxy) -methylsulfanyl-acetic acid In a procedure similar to that of Step 3 of Example 1, 3-bromo-7-methyl-quinolinyl- was hydrolyzed. 6-Oxy-2-methylthio-methyl acetate to obtain (3-bromo-7-methyl-quinolin-6-yloxy) -methylsulfanyl-acetic acid (M + 344). NMR H1 (DMSO). d ppm: 2.19 (3H, s); 2.42 (3H, s); 6.07 (1H, s); 7.42 (1H, s); 7.86 (1H, s); 8.52 (1H, s), 8.78 (1H, s), 13.55 (1H, s amp). Step: Preparation of 2- (3-bromo-7-methyl-quinolin-6-yloxy) -N-tert-butyl-2-methylsulphane-acetamide In a procedure similar to that of Step 4 of Example 1, acid was condensed - (3-bromo-7-methyl-quinolinyl-6-oxy) -2-methylthio acetic acid with t-butylamine to obtain 2- (3- bromo-7-methyl-quinolin-6-yloxy) -N-tert-butyl-2-methylsulfanyl-acetamide (mp 132-134 ° C, M + 344). NMR H1 (CDC13) d ppm: 1.44 (9H, s); 2.19 (3H, s); 2.49 (3H, s); 5.60 (1H, s); 6.48 (1H, s amp); 7.10 (1H, s); 7.89 (1H, s); 8.21 (1H, d), 8.78 (1H, d). The following amides were prepared using a similar procedure. Compound No. 16 of Table 13: using 1,1-dimethyl-propylamine, m.p. 135-137 ° C; NMR H1 (CDC13) d ppm: 0.88 (3H, t); 1.39 (6H, s); 1.79 (2H, c); 2.20 (3H, s); 2.48 (3H, s); 5.59 (1H, s); 6.39 (1H, s amp); 7.10 (1H, s); 7.89 (1H, s); 8.21 (1H, d); 8.78 (1H, d). Compound No. 238 of Table 13: using 1,1-dimethyl-prop-2-inylamine, m.p. 141-146 ° C; NMR H1 (CDC13) d ppm: 1.74 (6H, s); 2.19 (3H, s); 2.41 (1H, s); 2.50 (3H, s); 5.65 (1H, s); 6.77 (1H, s amp); 7.10 (1H, s); 7.89 (1H, s); 8.21 (1H, d); 8.78 (1H, d) '. Compound No. 52 of Table 13: using 2-amino-3-methoxy-2-methyl-propionitrile, NMR H1 (CDC13) d ppm: diastereomeric mixture (1/1); 1.81 and 1.83 (3H, 2xs); 2.20 and 2.21 (3H, 2xs); 2.48 (3H, s); 3.50 and 3.53 (3H, 2xs); 3.61-3.82 (2H, 2xdd); 5.72 and 5.75 (1H, 2xs); 7.11 and 7.13 (1H, 2xs); 7.32 and 7.34 (1H, 2xs amp); 7.90 (1H, s); 8.23 (1H, s); 8.79 (1H, s). Compound No. 221 of Table 13: using 1,1-dimethyl-2-prop-2-ynyloxy-ethylamine, m.p. 114-116 ° C; NMR H1 (CDC13) d ppm: 1.41 (3H, s); 1.44 (3H, s); 2.18 (3H, s); 2.50 (1H, t); 3.54 (2H, dd); 4.19 (2H, d); 5.61 (1H, s); 6.92 (1H, s amp); 7.10 (1H, s); 7.88 (1H, s); 8.22 (1H, d); 8.77 (1H, d). Compound No. 251 of Table 13: using 4-methoxy-1,1-dimethyl-but-2-inylamine, m.p. 129-132 ° C; NMR H1 (CDC13) d ppm: 1.73 (6H, s); 2.20 (3H, s); 2.49 (3H, s); 3.37 (3H, s); 4.11 (2H, s); 5.63 (1H, s); 6.76 (1H, s amp); 7.10 (1H, s); 7.89 (1H, s); 8.21 (1H, d); 8.78 (1H, d). EXAMPLE 3 This example illustrates the preparation of 2- (3-bromo-7-fluoro-quinolin-6-yloxy) -N-tert-butyl-2-methylsulfanyl-acetamide (Compound No. 12 of Table 6) Step 1: Preparation of 3-bromo-7-fluoro-quinolin-6-ol Step 1 In a procedure similar to that of Step 1, Step 1 of Example 1, 3-fluoro-4-methoxy-phenylamine (2 g) was treated in acetic acid. (25 ml) with 2,2,3 tribromopropanal (4.2 g) to obtain 3-bromo-7-fluoro-6-methoxy-quinoline (? + · 258). NMR H1 (CDCl3) d ppm: 4.02 (3H, s); 7.07 (1H, d); 7.75 (1H, d); 8.23 (1H, d); 8.78 (1H, d). Step 2 In a procedure similar to Step 1, Step 2 of Example 1, 3-bromo-7-fluoro-6-methoxy-quinoline from the previous step was treated with hydrobromic acid to obtain 3-bromo- 7-fluoro-quinolin-6-ol (M + 244). NMR H1 (DMSO-d6). d ppm: 7.35 (1H, d); 7.77 (1H, d); 8.59 (1H, d); 8.74 (1H, d), 10.93 (1H, s). Step 2: Preparation of (3-bromo-7-fluoro-quinolin-6-yloxy) -methylsulphanyl-acetic acid methyl ester In a procedure similar to that of Step 2, Step 2 of Example 1, 3-bromine was reacted -7-fluoro-quinolin-6-ol from the previous step with methyl 2-bromo-2-methylthioacetate from Step 2, Step 1 of Example 1, to obtain 3-bromo-7-fluoro-quinolinyl-6-oxy Methyl 2-methylthioacetate (M + 362). NMR H1 (CDC13) d ppm: 2.27 (3H, s); 3.89 (3H, s); 5.77 (1H, s) 7.26 (1H, d); 7.77 (1H, s); 8.23 (1H, s); 8.83 (1H, s). Step 3: Preparation of (3-bromo-7-fluoro-quinolin-6-yloxy) -methylsulfanyl-acetic acid In a procedure similar to that of Step 3 of the Example 1, 3-bromo-7-fluoro-quinolinyl-6-oxy-2-methylthio-methyl acetate was hydrolyzed to obtain (3-bromo-7-fluoro-quinolin-6-yloxy) -methylsulfanyl-acetic acid (M + 348). NMR H1 (DMSO-d6). d ppm: 6.16 (1H, s); 7.71 (1H, d) 7.90 (1H, d); 8.62 (1H, d), 8.88 (1H, d), 13.69 (1H, s amp). Step 4: Preparation of 2- (3-bromo-7-fluoro-quinolin-6-yloxy) -N-tert-buty1-2-methylsulphane-acetamide In a procedure similar to that of Step 4 of Example 1, acid was condensed 2- (3-bromo-7-fluoro-quinolinyl-6-oxy) -2-methylthio acetic acid with t-butylamine to obtain 2- (3- bromo-7-fluoro-quinolin-6-yloxy) -N-tert-butyl-2-methylsulfanyl-acetamide (mp 144-145 ° C, M + 403). N R H1 (CDC13) d ppm: 1.45 (9H, s); 2.19 (3H, s); 5.62 (1H, s); 6.62 (1H, s amp); 7.30 (1H, d); 7.79 (1H, d); 8.26 (1H, d), 8.84 (1H, d). The following amides were prepared using a similar procedure. Compound No. 238 of Table 6: using 1,1-dimethyl-prop-2-inylamine, m.p. 167-169 ° C; NMR H1 (CDCI3) d ppm: 1.75 (6H, s); 2.21 (3H, s); 2.41 (1H, s); 2.50 (3H, s); 5.68 (1H, s); 6.89 (1H, s amp); 7.33 (1H, d); 7.79 (1H, d); 8.26 (1H, d); 8.84 (1H, d). Compound No. 52 of Table 6: using 2-amino-3-methoxy-2-methyl-propionitrile, NMR H1 (CDCl3) d ppm: diastereomeric mixture (1/1); 1.81 and 1.83 (3H, 2xs); 2.21 and 2.22 (3H, 2xs); 3.52 and 3.54 (3H, 2xs); 3.64-3.84 (2H, 2xdd); 5.75 and 5. 76 (1H, 2xs); 7.33-7.36 (2H, m); 7.80 (1H, d); 8.28 (1H, d); 8.85 (1H, d). Compound No. 221 of Table 6: using 1,1-dimethyl-2-prop-2-ynyloxy-ethylamine, m.p. 115-117 ° C; NMR H1 (CDCl3) d ppm: 1.44 (3H, s); 1.46 (3H, s); 2.20 (3H, s); 2.45 (1H, t); 3. 61 (2H, dd); 4.20 (2H, d); 5.63 (1H, s); 6.90 (1H, s amp); 7. 28 (1H, d); 7.78 (1H, d); 8.26 (1H, d); 8.83 (1H, d). Compound No. 251 of Table 6: using 4-methoxy-1, l-dimethyl-but-2-inylamine, m.p. 115-117 ° C; NMR H1 (CDCl3) d ppm: 1.74 (6H, s); 2.21 (3H, s); 2.49 (3H, s); 3.38 (3H, s); 4. 12 (2H, s); 5.65 (1H, s); 6.88 (1H, s amp); 7.31 (1H, d); 7.79 (1H, d); 8.26 (1H, d); 8.84 (1H, d). Compound No. 244 of Table 6: using 1,1-dimethyl-but-2-inylamine, m.p. 130-132 ° C; NMR H1 (CDC13) d ppm: 1.70 (6H, s); 1.83 (3H, s); 2.21 (3H, s); 5.65 (1H, s); 6.86 (1H, s amp); 7.31 (1H, d); 7.78 (1H, d); 8.25 (1H, d); 8.84 (1H, d). Compound No. 68 of Table 6: using 2-ethoxy-1, 1-dimethyl-ethylamine, m.p. 111-113 ° C; NMR H1 (CDC13) d ppm: 1.21 (3H, t); 1.43 (H, s); 1.46 (3H, s); 2.20 (3H, s); 3.43 (2H, dd); 3.51-3.58 (2H, m), 5.63 (1H, s); 7.17 (1H, s amp); 7.28 (1H, d); 7.78 (1H, d); 8.25 (1H, d); 8.83 (1H, d). Compound No. 277 of Table 6: using 5-methoxy-1, 1-dimethyl-pent-2-inylamine, m.p. 104-106 ° C; NMR H1 (CDC13) d ppm: 1.71 (6H, s); 2.20 (3H, s); 2.48 (2H, t); 3.37 (3H, s); 3.50 (2H, t); 5.65 (1H, s); 6.88 (1H, s amp); 7.31 (1H, d); 7.79 (1H, d); 8.26 (1H, d); 8.84 (1H, d). Compound No. 256 of Table 6: using 6-chloro-l, l-dimethyl-hex-2-inylamine, m.p. 95-97 ° C; NMR H1 (CDC13) d ppm: 1.70 (6H, s); 1.96 (2H, quin); 2.20 (3H, s); 2.90 (2H, t); 3.68 (2H, t); 3.50 (2H, t); 5.66 (1H, s); 6.87 (1H, s amp); 7.31 (1H, d); 7.79 (1H, d); 8.26 (1H, d); 8.84 (1H, d). EXAMPLE 4 This example illustrates the preparation of 2- (3-iodo-7-fluoro-quinolin-6-yloxy) -N-tert-butyl-2-methylsulfanyl-acetamide (Compound No. 12 of Table 7) Step 1: Preparation of 3-iodo-6-hydroxyquinoline To a stirred mixture of 3-bromo-7-fluoro-6-hydroxyquinoline from Example 3, Step 1, Step 2 (0.50 g), sodium iodide (0.62 g) and copper iodide (0.08 g) in dioxane (3.0 ml) was added N, N, N ', N' -tetramethyl-ethane-1,2-diamine (0.07 g) in a sealed tube. The mixture was stirred at 120 ° C for 14 hours and after cooling it was treated with aqueous ammonia and then aqueous hydrochloric acid. Extraction with ethyl acetate, drying of the organic phase over magnesium sulfate, filtration and evaporation under reduced pressure gave the desired product (M + 290) as a light brown powder which was used as such in the following He passed. NMR H1 (CDC13). d ppm: 7.30 (1H, d); 7.72 (1H, d); 8.02 (1H, d), 8.73 (1H, d); 8.83 (1H, d), 10.88 (1H, s). Step 2: Preparation of N-tert-butyl-2- (3-iodo-7-fluoro-quinolin-6-yloxy) -2-methylsulfanyl-acetamide In a procedure similar to that of Step 2, Step 1 of Example 1 , 3-iodo-7-fluoro-6-hydroxy-quinoline was reacted with ethyl ester of chloromethylsulfanyl-acetic acid to obtain ethyl ester of (3-iodo-7-fluoro-quinolin-6-yloxy) -methylsulfanyl- acetic acid (M + 408). In a procedure similar to that of Step 3 of Example 1, (3-iodo-7-fluoro-quinolin-6-yloxy) -methylsulfanyl-acetic acid ethyl ester was hydrolyzed to obtain (3-iodo-7-fluoro- quinolin-6-yloxy) -methylsulfanyl-acetic acid (M + 394). In a procedure similar to that of Step 4 of Example 1, (3-iodo-7-fluoro-quinolin-6-yloxy) -methylsulfanyl-acetic acid was condensed with t-butylamine to obtain N-tert-butyl-2- ( 3-iodo-quinolin-6-yloxy) -2-methylsulfanyl-acetamide as a white solid (mp 165-166 ° C, M + 449). NMR H1 (CDC13) .5 ppm: 1.44 (9H, s); 2.18 (3H, s); 5.60 (1H, s); 6.62 (1H, s amp); 7.27 (1H, d); 7.76 (1H, dd); 8.47 (1H, d); 8.97 (1H, d). The following amides were prepared using a. similar procedure. Compound No. 238 of Table 7: using 1,1-dimethyl-prop-2-inylamine, m.p. 150-152 ° C; NMR H1 (CDC13) d ppm: 1.75 (6H, s); 2.20 (3H, s); 2.40 (1H, s); 5.66 (1H, s); 6.88 (1H, s amp); 7.27 (1H, s); 7.77 (1H, s); 8.47 (1H, d); 8.97 (1H, d). Compound No. 52 of Table 7: using 2-amino-3-methoxy-2-methyl-propionitrile, NMR H1 (CDC13) d ppm: diastereomeric mixture (1/1); 1.82 and 1.84 (3H, 2xs); 2.20 and 2.22 (3H, 2xs); 3.53 and 3.54 (3H, 2xs); 3.64-3.84 (2H, 2xdd); 5.73 and 5.75 (1H, 2xs); 7.27-7.36 (3H, m); 7.77 (1H, d); 8.49 (1H, d); 8.98 (1H, s). Compound No. 244 of Table 7: using 1,1-dimethyl-but-2-inylamine, m.p. 142-145 ° C; NMR H1 (CDC13) d ppm: 1.70 (6H, s); 1.83 (3H, s); 2.20 (3H, s); 5.64 (1H, s); 6.87 (1H, s amp); 7.27 (1H, d); 7.76 (1H, d); 8.47 (1H, d); 8.96 (1H, d). Compound No. 251 of Table 7: using 4-methoxy-1,1-dimethyl-but-2-inylamine, m.p. 110-112 ° C; NR H1 (CDC13) d ppm: 1.74 (6H, s); 2.20 (3H, s); 3.38 (3H, s); 4.13 (2H, s); 5.65 (1H, s); 6.89 (1H, s amp); 7.27 (1H, d); 7.78 (1H, d); 8.47 (1H, d); 8.97 (1H, d).
EXAMPLE 5 This example illustrates the preparation of N-tert-butyl-2- (7-fluoro-3-thiophen-3-yl-quinolin-6-yloxy) -2-methylsulfanyl-acetamide (Compound No. 12 of Table 30 ). Step 1: A stirred mixture of 2- (3-bromo-7-fluoro-quinolin-6-yloxy) -N-tert-butyl-2-methylsulfanyl-acetamide of Example 3, Step 4 (160 mg), chloride was heated of bis (triphenylphosphine) aladio (II) (1.4 mg), 3-thiophene boronic acid (56 mg) and sodium carbonate and hydrogen (101 mg) in dioxane / water (1: 1 mixture, 4.8 ml) at 70 ° C for 14 hours. After cooling, the reaction mixture was treated with sodium carbonate and saturated aqueous hydrogen (5 ml). Extraction with ethyl acetate, drying of the organic phase over magnesium sulfate, filtration and evaporation under reduced pressure gave the crude product which was fractionated by chromatography (silica, hexane / ethyl acetate, 2: 1 by volume). to obtain the desired product in the form of a white solid (mp 170-173 ° C, M + 405). NMR H1 (CDC13) d ppm: 1.46 (9H, s); 2.20 (3H, s); 5.64 (1H, s); 6.66 (1H, s amp); 7.42 (1H, d); 7.51 (2H, m); 7.66 (1H, m), 7.80 (1H, d), 8.22 (1H, d); 9.13 (1H, d). The next amide was prepared using a similar procedure. 2- (7-Fluoro-3-thiophen-3-yl-quinolin-6-yloxy) -N- (4-methoxy-1, 1-dimethyl-but-2-ynyl) -2-methyl-sulfanyl- acetamide (Compound No. 251 of Table 30) pf 132-134 ° C; NMR H1 (CDC13) d ppm: 1.75 (6H, s); 2.22 (3H, s); 3.39 (3H, s); 4.13 (2H, s); 5.68 (1H, s); 6.93 (1H, s amp); 7.42 (1H, d); 7.51 (2H, m); 7.66 (1H, m), 7.82 (1H, d), 8.22 (1H, d); 9.13 (1H, d), from 2- (3-bromo-7-fluoro-quinolin-6-yloxy) -N- (4-methoxy-1,1-dimethyl-but-2-ynyl) -2- methylsulfanyl acetamide of Example 3, Step 4, above.
EXAMPLE 6 This Example illustrates the fungicidal properties of the compounds of formula (I). The compounds were evaluated by a foliar disk test, according to the methods described below. The test compounds were dissolved in DMSO and diluted in water at 200 ppm. In the case of the Pythium ultimum test, they were dissolved in DMSO and diluted in water to 20 ppm. Erysiphe graminís f.sp. trítici (powdery mildew) of wheat): segments of wheat leaves were placed on agar in a 24 cavity plate and sprayed with a solution of the test compound. After allowing to dry completely, for 12 to 24 hours, the leaf discs were inoculated with a spore suspension of the fungus. After the proper incubation, the activity of a compound was confirmed four days after the inoculation as a preventive fungicidal activity. Puccinia recondite f.sp. tritici (brown wheat blight): Wheat leaf segments were placed on agar in a 24-well plate and sprayed with a solution of the test compound. After allowing to dry completely, during 12 to 24 hours, the leaf discs were inoculated with a suspension of spores of the fungus. After the proper incubation, the activity of a compound was confirmed nine days after the inoculation as a preventive fungicidal activity. Septoria nodorum (wheat glume blotch): Wheat leaf segments were placed on agar in a 24 cavity plate and sprayed with a solution of the test compound. After allowing to dry completely, during 12 to 24 hours, the leaf discs were inoculated with a suspension of spores of the fungus. After the proper incubation, the activity of a compound was confirmed four days after inoculation as a fungicidal activity preventive Pyrenophora teres (barley net blotch): Segments of barley leaves were placed on agar in a 24 cavity plate and sprayed with a solution of the test compound. After allowing to dry completely, during 12 to 24 hours, the leaf discs were inoculated with a suspension of spores of the fungus. After the proper incubation, the activity of a compound was confirmed four days after the inoculation as a preventive fungicidal activity. Pyricularia oryzae ("burned" from rice): Segments of rice leaves were placed on agar in a 24 cavity plate and sprayed with a solution of the test compound. After allowing to dry completely, during 12 to 24 hours, the leaf discs were inoculated with a suspension of spores of the fungus. After the proper incubation, the activity of a compound was confirmed four days after the inoculation as a preventive fungicidal activity. Botrytis cinerea (gray mold): discs of bean leaves were placed on agar in a 24 cavity plate and sprayed with a solution of the test compound. After allowing to dry completely, during 12 to 24 hours, the leaf discs were inoculated with a suspension of spores of the fungus. After the proper incubation, the activity of a compound four days after inoculation as a preventive fungicidal activity. Phytophthora infestans (late potato blight in tomato): Tomato leaf discs were placed on aqueous agar in a 24 cavity plate and sprayed with a solution of the test compound. After allowing to dry completely, during 12 to 24 hours, the leaf discs were inoculated with a suspension of spores of the fungus. After the proper incubation, the activity of a compound was confirmed four days after the inoculation as a preventive fungicidal activity. Plasmopara viticola (Downy mildew of vineyards): Vine leaf discs were placed on agar in a 24-well plate and sprayed with a solution of the test compound. After allowing to dry completely, during 12 to 24 hours, the leaf discs were inoculated with a suspension of spores of the fungus. After the proper incubation, the activity of a compound was confirmed seven days after the inoculation as a preventive fungicidal activity. Septoria tritici (leaf spot): Cryogenically stored fungi conidia were mixed directly in nutrient broth (PDB potato dextrose broth). After placing a solution (DMSO) of the test compounds in a microtitre plate (96 cavity format) the nutrient broth with fungal spores. The test plates were incubated at 24 ° C and the inhibition of growth was determined by photometry 72 hours later. Fusarium culmorum (root rot): Cryogenically stored mushroom conidia were mixed directly in nutrient broth (PDB potato dextrose broth). After placing a solution (DMSO) of the test compounds in a microtitre plate (96 cavity format) the nutrient broth was added with the fungal spores. The test plates were incubated at 24 ° C and the inhibition of growth was determined by photometry 48 hours later. Pythium ultimum (drowning): Fragments of mushroom mycelia, prepared from a fresh liquid culture broth, were mixed in potato dextrose broth. A solution of the test compound in dimethyl sulfoxide was diluted with water at 20 ppm and then placed in a 96-well microtiter plate and the nutrient broth was added with the fungal spores. The test plate was incubated at 24 ° C and the inhibition of growth was determined by photometry 48 hours later. With the following compounds (number of the compound first, followed by the table number in parentheses) at least 60% control of the following fungal infections at 200 ppm was obtained: Plasmopara viticola, compounds 9 (6), 12 (7), 38 (6), 52 (6), 52 (7), 60 (6), 95 (6), 221 (6), 221 (13), 235 (6), 238 (7), 238 (10), 244 (6), 244 (7), 251 (2), 251 (7), 251 (10), 251 (13), 251 (30), 256 (6), 264 (6), 277 (6), 278 (6), Phytophthora infestans, compounds 12 (6), 12 (10), 52 (7), 52 (13), 221 (6), 221 (13), 238 (7), 238 (10), 238 (13), 244 (6), 244 (7), 251 (7), 251 (10), 256 (6), 275 (7), 277 (6), 278 (6), Erysiphe graminis f.sp. tritici, compounds 9 (6), 12 (6), 12 (13), 28 (6), 38 (6), 52 (6), 52 (7), 52 (13), 68 (6), 86 (6), 181 (6), 189 (6), 221 (6), 221 (13), 235 (6), 238 (6), 238 (7), 238 (10), 238 (13), 244 (6), 251 (6), 251 (7), 251 (13), 251 (30), 256 (6), 264 (6), 268 (6), 275 (6), 275 (7), 277 (6), 278 (6), 281 (6), 284 (6), Pyricularia oryzae, compounds 9 (6), 52 (6), 52 (7), 68 (6), 221 (6), 238 (6), 244 (7), 251 ( 6), 251 (7), 275 (7), 277 (6), 278 (6), Puccinía recondita f.sp. tritici, compounds 52 (6), 52 (7), 68 (6), 221 (6), 238 (7), 251 (2), 264 (6), Septoria nodorum, compounds 9 (6), 12 (2) ), 12 (7), 12 (10), 12 (13), 12 (30), 52 (6), 52 (7), 68 (6), 221 (6), 235 (6), 238 (6 ), 238 (7), 244 (6), 244 (7), 244 (13), 251 (6), 251 (7), 251 (13), 256 (6), 264 (6), 277 (6 ), 278 (6), 281 (6), Septoria tritici, compounds 9 (6), 12 (6), 12 (7), 12 (13), 16 (13), 38 (6), 52 (2) , 52 (6), 52 (7), 52 (13), 68 (6), 95 (6), 122 (6), 221 (6), 221 (13), 224 (6), 235 (6) , 238 (6), 238 (7), 238 (13), 244 (2), 244 (6), 244 (7), 251 (6), 251 (7), 251 (13), 251 (2), 251 (30), 256 (6), 264 (6), 268 (6), 275 (7), 277 (6), 278 (6), 281 (6), 284 (6), 287 (6), 291 (6), Fusarium culmorum, compounds 9 (6), 12 (6), 12 (7), 221 (6), 238 (6), 238 (7), 244 (6), 244 ( 7), 251 (6), 251 (7), 251 (13), 284 (6). With the following compounds (number of compound first, followed by the table number in parentheses) at least 60% control of the following 20 ppm fungal infection was obtained: Pythium ultimum, compounds 9 (6), 12 (10) , 52 (6), 52 (13), 221 (6), 221 (13), 235 (6), 238 (6), 244 (6), 251 (6), 251 (10), 251 (13) , 251 (30), 264 (6), 275 (7), 278 (6), 281 (6). It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims (4)

    CLAIMS Having described the invention as above, the content of the following claims is claimed as property: 1. A compound of the General Formula I ) characterized in that Q1 r Q2 and Q3 r independently of one another, are halogen, cyano, nitro, azido, optionally substituted (Ci-6) alkyl, optionally substituted (C3-6) cycloalkyl, optionally substituted (C3-6) heterocyclyl, which contains at least one heteroatom selected from sulfur, oxygen or NR °, where R ° is hydrogen or optionally substituted (C1-6) alkyl, (C3-6) cycloalkyl optionally substituted (C1-4) alkyl, (C2-) alkenyl 6) optionally substituted, optionally substituted (C 2-6) alkynyl, optionally substituted (C 1-6) alkoxy, optionally substituted C 2-6 alkenyloxy, optionally substituted C 2-6 alkynyloxy, optionally substituted aryl, optionally substituted aryloxy, arylalkyl (Ci ~ 6) optionally substituted, arylalkoxy (Ci ~ 6) optionally substituted, heteroaryl optionally substituted, optionally substituted heteroaryloxy, optionally substituted heteroarylalkyl (Ci-e), optionally substituted heteroarylalkoxy (Ci ~ 6), -SF 5 or -S (0) alkyl (C 1-6), where u is 0, 1 or 2 and the group alkyl is optionally substituted with halogen, or Q1 f Q2 and Q3, independently of each other, are -0S02 (C1-4) alkyl, where the alkyl group is optionally substituted with halogen, or Q1, Q2 and Q3, independently of each other, are -CONRuRv, -CORu, -C02Ru, -CRU = NRV, -NRURV,
  1. -NRuC0Rv, -NRuC02Rv, -S02NRuRv or -NRuS02Rw, where Rw is optionally substituted alkyl (Ci-6) and Ru and Rv, independently of each other, are hydrogen or alkyl (???) optionally substituted with halogen, or, in the case of -C0NRuRv or -S02NRuRv, RURV can be joined to form a 5- or 6-membered carbocyclic or heterocyclic ring containing a heteroatom selected from sulfur, oxygen and NR °, where R ° is hydrogen or alkyl (Ci-e) optionally substituted, or, in the case of -CRU = NRV, R is hydroxy or optionally substituted alkoxy (Ci ~ 6), optionally substituted aryloxy or optionally substituted heteroaryloxy, or Q1 and Q2, independently of each other, further indicate hydrogen, R1 is optionally substituted (C1-4) alkyl, optionally substituted (C2-4) alkenyl, (C2-4) alkynyl optionally substituted or optionally substituted cycloalkyl (C3-4), R2 is hydrogen, alkyl (Ci-s), cycloalkyl (C3-4), alkenyl (C2-8) cyano, hydroxy, alkoxy, cyano (C1-4) alkyl, alkoxy (C 1-4) (C 1-4) alkyl, (C 1-4) alkoxy (1-4) alkoxy (C 1-4) alkyl or (C 1-4) benzyloxyalkyl, wherein the phenyl ring is optionally substituted with alkoxy ( C1-4), R3 is - (CRaRb) p (CRcRd) q (X) r (CReRf) sR4, where Ra, Rb, Rc, Rd, Re and Rf, independently of each other, are hydrogen, alkyl (C1-) ), halogen, cyano, hydroxy, (1-4C) alkoxy or (1-4C) alkoxycarbonyl, or RaRb, RcRd or ReRf can be joined to form a 3- to 8-membered carbocyclic or heterocyclic ring containing a heteroatom selected from sulfur , oxygen and NR °, where R ° is hydrogen or optionally substituted alkyl (Ci-6), X is (CO), (CO) O, O (CO), O, S (0) t, where t is 0, what 2, or X is NH or Nalkyl (Ci-6), p, rys, independently of each other, are 0 or 1, q is 0, 1 or 2, R4 is optionally substituted (Ci-6) alkyl, (C2-6) alkenyl optionally substituted, -CRUU = NRVV, where Ruu is hydrogen or alkyl (C! -6) and Rvv is optionally substituted hydroxy or (C1-6) alkoxy, optionally substituted aryloxy or optionally substituted heteroaryloxy, or -CH2-C = C-R5, where
  2. R5 is hydrogen, alkyl (Ci_-8) optionally substituted with halogen, hydroxy, alkoxy (Ci-6), alkoxy (Ci ~
  3. 3) (C 1-3) alkoxy, cyano, C 1-4 alkylcarbonyloxy, aminocarbonyloxy, mono- or di (C 1-
  4. 4) alkylaminocarbonyloxy, trialkyl (C 1-4) silyloxy or -S (0) galkyl ( ? -6), where g is 0, 1 or 2, or R5 is (C3-6) cycloalkyl optionally substituted with halogen, hydroxy, (Ci-6) alkoxy, (1-3C) alkoxy (Cx-3) alkoxy, cyano, (C 1-4) alkyloxycarbonyloxy, aminocarbonyloxy, mono- or dialkyl (C 1-4) aminocarbonyloxy, trialkyl (C 1-4) 4) silyloxy or -S (O) galkyl (Ci ~ 6), where g is 0, 1 or 2, or R 5 is (C 3-6) cycloalkyl (C 1-4) alkyl, wherein the alkyl and / or cycloalkyl portion is optionally substituted with halogen, hydroxy, alkoxy (Ci-e), (1-3C) alkoxy (1-3C) alkoxy, cyano, (1-4C) alkyloxyloxy, aminocarbonyloxy, mono- or di (C1-4) alkyl aminocarbonyloxy, trialkyl (1-4C) silyloxy or -S (O) galkyl (Ci ~ 6), where g is 0, 1 or 2, or R5 is optionally substituted aryl, optionally substituted arylalkyl, optionally substituted aryloxyalkyl (??? 4), optionally substituted heteroaryl or optionally substituted (C1-4) heteroarylalkyl or optionally substituted (C1-4) heteroaryloxyalkyl, or R4 is optionally substituted (C3-6) cycloalkyl, optionally substituted (C5-6) cycloalkenyl, optionally substituted aryl, optionally substituted heteroaryl or a ring from 5 to 8 members optionally substituted that optionally contains a heteroatom selected from sulfur, oxygen or NR °, where R ° is hydrogen or optionally substituted alkyl (Ci-6), or when R3 is - (CRaRb) p (CRcRd) q (X) r (CReRf) SR4, R2 and R3 can be joined to form a 5 or 6 membered ring optionally substituted with halogen, (C1-4) alkyl, mono- or di (C1-4) alkylaminocarbonyl, and optionally containing a heteroatom selected from sulfur, oxygen and NR00, wherein R00 is (0? -4) alkyl optionally substituted with halogen, (Ci-6) alkoxy or cyano, or R00 is phenyl optionally substituted with nitro, (C1-4) alkyl, (C1-4) haloalkyl , (1-4C) alkylcarbonyl or heteroaryl, or R 2 and R 3 can be joined to form an optionally substituted 6.6-membered bicyclic, R 3 is - (CR 30 R 40) C = CR 50, where R 30 and R 40, independently of one another, they are hydrogen, alkyl (Ci-e), haloalkyl (C1-4), alkoxy (Ci-4) alkyl (C1-3), alkenyl (C2-3) or alkynyl (C2-3), or R30 and R40 are joined with the carbon atom to which they are attached to form a 3-6 membered carbocyclic or heterocyclic ring containing a heteroatom selected from sulfur, oxygen or NR000, where R000 is hydrogen or (C1-4) alkyl, where the carbocyclic or heterocyclic ring is optionally substituted with halo or (1-4C) alkyl, R is hydrogen, optionally substituted (C1-4) alkyl, optionally substituted (C3-6) cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl containing a heteroatom selected from sulfur, oxygen or NR000, where R000 is hydrogen or alkyl (Ci_6) , L is sulfur or oxygen, and n is 0, 1 or 2, and salts and N-oxides of the compounds of Formula I. 2. Compounds according to claim 1, characterized in that Q2 is hydrogen, Q1 and Q3 is in accordance with claim 1. 3. Compounds according to claim 1, characterized in that Q1 is halogen, aryl or heteroaryl, Q2 is hydrogen and Q3 is according to claim 1. 4. Compounds in accordance with the claim 1, characterized in that Q1 is aryl, Q2 is hydrogen and Q3 is according to claim 1. 5. Compounds according to claim 1, characterized in that Q1 is heteroaryl, Q2 is hydrogen and Q3 is according to claim 1. 6. Compounds according to claim 1, characterized in that Q1 and Q3 are halogen and Q2 is hydrogen. 7. Compounds according to claim 1, characterized in that Q1 is aryl or heteroaryl, Q2 is hydrogen and Q3 is halogen. Compounds according to claim 1, characterized in that Q1 and Q2 are hydrogen and Q3 is halogen or optionally substituted alkyl. 9. Compounds in accordance with the claim 1, characterized in that Q1 is halogen, Q2 is hydrogen and Q3 is optionally substituted alkyl. 10. Compounds according to claim 1, characterized in that Q1 and Q2 are halogen and Q3 is optionally substituted alkyl. 11. Compounds according to claim 1, characterized in that Q1 is bromine. 12. Compounds according to claim 1, characterized in that Q1 is iodine. 13. Compounds in accordance with the claim 1, characterized because Q1 is chlorine. 14. Compounds according to claim 1, characterized in that Q1 is fluoro. 15. Compounds according to claim 1, characterized in that Q3 is halogen. 16. Compounds according to claim 1, characterized in that Q3 is fluoro. 17. Compounds according to claim 1, characterized in that Q1 is bromine, Q2 is hydrogen and Q3 is fluoro. 18. Compounds according to claim 1, characterized in that Q1 is bromine, Q2 is hydrogen and Q3 is chlorine. 19. Compounds according to claim 1, characterized in that Q1 is iodine, Q2 is hydrogen and Q3 is fluoro. 20. Compounds according to claim 1, characterized in that Q1 is iodine, Q2 is hydrogen and QJ is chlorine. 21. Compounds in accordance with the claim 1, characterized in that Q1 is hydrogen, halogen, aryl or heteroaryl. 22. Compounds according to claim 1, characterized in that R1 is alkyl (Ci-4) or haloalkyl (Ci ~ 4) · 23. Compounds according to claim 1, characterized in that R1 is methyl. 24. Compounds according to claim 1, characterized in that R1 is ethyl. 25. Compounds in accordance with the claim 1, characterized in that R2 is hydrogen or methyl. 26. Compounds according to claim 1, characterized in that R2 is hydrogen. 27. Compounds according to claim 1, characterized in that Q1, Q2 and Q3 are halogen. 28. Compounds according to claim 1, characterized in that Q1 is halogen, Q2 is alkyl (Ci-4) and Q3 is halogen. 29. Compounds according to claim 28, characterized in that Q1 is halogen, Q2 is alkyl (Ci-4) and Q3 is chloro. 30. Compounds according to claim 28, characterized in that Q1 is halogen, Q2 is alkyl (Ci-4) and Q3 is fluoro. 31. Compounds according to claim 1, characterized in that Q1 is halogen, Q2 is methyl and Q3 is halogen. 32. Compounds according to claim 31, characterized in that Q1 is halogen, Q2 is methyl and Q3 is chloro. 33. Compounds according to claim 31, characterized in that Q1 is halogen, Q2 is methyl and Q3 is fluoro. 34. Compounds according to claim 31, characterized in that Q1 is bromine, Q2 is methyl and Q3 is chlorine. 35. Compounds according to claim 31, characterized in that Q1 is bromine, Q2 is methyl and Q3 is fluoro. 36. Compounds in accordance with the claim 31, characterized in that Q1 is iodine, Q2 is methyl and Q3 is chlorine. 37. Compounds according to claim 31, characterized in that Q1 is iodine, Q2 is methyl and Q3 is fluoro. 38. Compounds according to claim 1, characterized in that Q1 is halogen and Q2 and Q3 are alkyl (Ci-4). 39. Compounds according to claim 1, characterized in that R3 is tere-butyl, l-halo-2-methylprop-2-yl, 1, l-dihalo-2-methylprop-2-yl, 1, 1, 1- trihalo-2-methylprop-2-yl, l-alkoxy-2-methylprop-2-yl, 1-alkenyloxy-2-methylprop-2-yl, l-alkynyloxy-2-methylprop-2-yl, 1-cyano- 2-methyl-prop-2-yl, l-alkoxyalkoxy-2-methyl-prop-2-yl, 1-halo-3-methylbut-3-yl, 1, l-dihalo-3-methylbut-3-yl, 1, 1, 1-trihalo-3-methylbut-3-yl, l-alkoxy-3-methylbut-3-yl, l-alkenyloxy-3-methylbut-3-yl, l-alkynyloxy-3-methylbut-3- ilo, l-cyano-3-methylbut-3-yl, 2-cyanoprop-2-yl, 2-methoxycarbonylprop-2-yl or 2-methylaminocarbonylprop-2-yl, l-alkylthio-2-methylprop-2-yl, 1-Alkylsulfinyl-2-methylprop-2-yl, 1-alkylsulfonyl-2-methylprop-2-yl, 2-cyano-l-alkoxyprop-2-yl, 2-methyl-1- [(E and / or Z) -hydroxyimino] -prop-2-yl, 2-methyl-l- [(E and / or Z) -alkoxyimino] -prop-2-yl, 2-methyl-l- [(E and / or Z) -aryloxyimino] ] -prop-2-yl, 2-methyl-l- [(E and / or Z) -heteroaryloxyimino] -prop-2-yl, l-alkoxy-prop-2-yl, l-halo-prop-2-yl, 3-methyl-but-l-in- 3-yl, l-alkyl-3-methyl-but-l-in-3-yl, 4-methyl-pent-2-yn-4-yl, l-hydroxy-4-methyl-pent-2-yl 4-yl, l-alkoxy-4-methyl-pent-2-yn-4-yl, l-alkoxyalkoxy-4-methyl-pent-2-yn-4-yl, 1-alkoxyalkoxyalkyl-4-methyl-pent 2-in-4-yl, l-cyanoalkyl-3-methylbut-3-yl, l-haloalkyl-3-methylbut-3-yl. 40. Compounds according to claim 39, characterized in that R3 is tere-butyl, l-halo-2-met ilprop-2-yl, 1-fluoro-2-methylprop-2-yl, l-methoxy-2-methylprop -2-ilo, l-ethoxy-2-methylprop-2-yl, l-allyloxy-2-methylprop-2-yl, 1- (prop-2-ynyloxy) -2-methylprop-2-yl, 2-cyano-l-ethoxy -prop-2-yl, 2-cyano-l-methoxyprop-2-yl, 1-halo-3-methylbut-3-yl, 1-fluoro-3-methylbut-3-yl, 3-methylbut-l-in -3-yl, 4-methylpent-2-yn-4-yl, 5-methyl-hex-3-yn-5-yl, 1-methoxy-4-methyl-pent-2-yn-4-yl, l -alloyloxy-4-methyl-pent-2-yn-4-yl, l-propargyloxy-4-methyl-pent-2-yn-4-yl, l-ethoxy-4-methyl-pent-2-in- ilo. 41. Compounds according to claim 1, characterized in that R4 is (Ci-6) alkyl optionally substituted with (Ci-4) alkoxy (Ci-4) alkyl (Ci-4), where the alkyl group is optionally substituted with halo, mono- or di-alkyl (Ci ~ 6) amino or trialkyl (Ci-4) silyl, or R4 is alkyl (??? 6) optionally substituted with benzyloxyalkyl (Ci-4), where the alkyl group is optionally substituted with halo, mono- or di-alkyl (Ci ~ 6) amino or trialkyl (Ci-4) silyl, or R4 is (Ci-6) alkyl optionally substituted with (C2-6) alkenyloxy or -S (0) xalkyl (Ci-g), where x is 0, 1 or 2 and the alkyl group is optionally substituted with halo, mono- or di-alkyl (Ci-6) amino, -NHalkyl (Ci-4) = NOR, where R is hydrogen or (C 1-4) alkyl, or where the alkyl group is optionally substituted with trialkyl (C 1-4) silyl, or R 4 is -CRUU = NRVV, where Ruu is hydrogen or (Ci-6) alkyl and Rvv is optionally substituted hydroxy or (Ci-6) alkoxy. 42. Compounds according to claim 1, characterized in that the rings or optionally substituted aryl portions and optionally substituted heteroaryl of the R5 values are optionally substituted with halogen, cyano, nitro, azido, alkyl (Ci-6), haloalkyl (Ci-6), 6), (C3-6) cycloalkyl, (C3-e) cycloalkyl (C1-4) alkyl, (C2-6) alkenyl, (C2-6) haloalkenyl, (C2-6) alkynyl (C2-6) haloalkynyl, alkoxy (Ci ~ 6), haloalkoxy (Ci-6), alkenyloxy (C2-6) haloalkenyloxy (C2-6), alkynyloxy (C2-6), haloalkynyloxy (C2-6), aryl, aryloxy, arylalkyl (C1-6) ), arylalkoxy (Ci-d), heteroaryl, heteroaryloxy, heteroarylalkyl (Ci-e), heteroarylalkoxy (Ci-β), -SF 5, -S (0) galkyl (C 1-4) where g is 0, 1 or 2 and the alkyl is optionally substituted with halo, or R5 is optionally substituted with -0S02 (C1-4) alkyl, wherein the alkyl group is optionally substituted with halo, or R5 is optionally substituted with -CONRgRh, -CORg, -C02Rg, -Rg = NRh, -NRgRh, -NRgCORh, -NRgC02Rh, -S02NRgRh or -NRgS02Ri, where R1 is (Ci- 6) alkyl optionally substituted with halogen and Rg and Rh, independently of each other, are hydrogen or (C i -6) alkyl optionally substituted with halogen, or, in the case of -CONRgRh or -S02NRgRh, RgRh can be join to form a 5- or 6-membered carbocyclic or heterocyclic ring containing a heteroatom selected from sulfur, oxygen or NR °, where R ° is hydrogen or optionally substituted alkyl (Ci-6). 43. Compounds, according to claim 1, characterized in that the optionally substituted aryl, optionally substituted heteroaryl or the optionally substituted 5 to 8 membered ring R4 is optionally substituted with halogen, cyano, nitro, azido, alkyl (Ci-6) , haloalkyl (Ci ~ 6), cycloalkyl (C3-6), cycloalkyl (C3-6) alkyl (C1-4), alkenyl (C2-6), haloalkenyl (C2-6), alkynyl (C2-6), haloalkynyl (C2-6), alkoxy (Ci-6), haloalkoxy (Ci-6), alkenyloxy (C2-6), haloalkenyloxy (C2-6), alkynyloxy (C2-6), haloalkynyloxy (C2-6), -SF5 , -S (0) x-alkyl (Ci ~ 6), where x is 0, 1 or 2 and the alkyl group is optionally substituted with halo, or R4 is optionally substituted with -0S02 (C1-4) alkyl, where the group . alkyl is optionally substituted with halogen, -CONRxRy, -CON (ORx) Ry, -CORx, -C02Rx, -CR: = NRy, -NRXRY, -NRxCORY, -NRxC02Ry, -S02NRxRy or -NRxS02Rz, where Rz is alkyl (Ci) 8) optionally substituted with halogen and R x and R y, independently of one another, are hydrogen or (C 1-6) alkyl optionally substituted with halogen 44. Compounds according to claim 1, characterized in that R50 is (Ci-4) alkyl optionally substituted with halogen, hydroxy, alkoxy (Ci-6), alkenyl (C2-e) r alkynyl (C2-6) f alkoxy ( C1-4) alkoxy (Ci-4), cyano, alkyl (Ci-4) carbonyloxy, aminocarbonyloxy, mono- or di (C1-4) alkyl amino-carbonyloxy, S (0) palky (Ci-6), where p is 0, 1 or 2, triazolyl, pyrazolyl, imidazolyl, trialkyl (1-4C) silyloxy, optionally substituted phenoxy, optionally substituted thienyloxy, optionally substituted benzyloxy or optionally substituted thienylmethoxy. 45. Compounds according to claim 1, characterized in that R50 is (C3-6) cycloalkyl optionally substituted by halogen, hydroxy, alkoxy (Ci-6), alkoxy (C1-4) alkoxy (C1-4), cyano, alkyl (C 1-4) carbonyloxy, aminocarbonyloxy, mono- or di (C 1-4) alkyl amino-carbonyloxy, S (0) palky (Ci-6), where p is 0, 1 or 2, triazolyl, pyrazolyl, imidazolyl, trialkylsilyloxy (C1-4), optionally substituted phenoxy, optionally substituted thienyloxy, optionally substituted benzyloxy or optionally substituted thienylmethoxy. 46. Compounds according to claim 1, characterized in that the optionally substituted aryl or the optionally substituted heteroaryl R50 is optionally substituted by halogen, hydroxy, mercapto, (C1-4) alkyl, alkenyl (C 2-4), alkynyl (C 2-4) alkoxy (C 1-4), alkenyloxy (C 2-4), alkynyloxy (C 2-4), haloalkyl (C 1-4), haloalkoxy (C 1-4), alkylthio ( C1-4), haloalkylthio (C1-4), hydroxyalkyl (C1-4), alkoxy (C1-4) alkyl (C1-4), cycloalkyl (C3-6), cycloalkyl (C3-6) alkyl (C1-4) ), phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanate, isothiocyanate, nitro, NRpRq, NHCORp, -NHCONRpRq, CONRpRq, -S02R °, OS02R °, CORp, CRp = NRq or N = CRpRq, where R ° is alkyl ( C1-4), haloalkyl (C1-4), alkoxy (C1-4), haloalkoxy (Ci-4), alkylthio (C1-4), cycloalkyl (C3-6), cycloalkyl (C3-6) alkyl (C1-6) 4), phenyl or benzyl, the phenyl and benzyl groups are optionally substituted with halogen, (1-4C) alkyl or (1-4C) alkoxy, and Rp and Rq are independently hydrogen, (1-4C) alkyl, haloalkyl (C1 -4), (C 1-4) alkoxy, (C 1-4) haloalkoxy, (C 1-4) alkylthio, (C 3-6) cycloalkyl, (C 3-6) cycloalkyl (C 1-4) alkyl, phenyl or benzyl, phenyl and benzyl groups are or optionally substituted with halogen, (1-4C) alkyl or (C1-) alkoxy. 47. Compounds according to claim 1, characterized in that L is oxygen. 48. Compounds in accordance with the claim 1, characterized in that n is 0. 49. A process, characterized in that it is for preparing a compound of the Formula I according to claim 1 as described herein. 50. A fungicidal composition, characterized because it comprises an effective fungicidal amount of a compound according to claim 1 and a suitable carrier or diluent therefor. 51. A method for combating or controlling phytopathogenic fungi, characterized in that it comprises applying an effective fungicidal amount of a compound according to claim 1 to a plant, to a seed of a plant, to the locus of the plant or seed or to the soil or any other means for the growth of a plant.
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