WO2012146535A1 - Process for the preparation of 2-substituted 2,4-dihydro-[1,2,4]triazole-3-thiones - Google Patents

Process for the preparation of 2-substituted 2,4-dihydro-[1,2,4]triazole-3-thiones Download PDF

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WO2012146535A1
WO2012146535A1 PCT/EP2012/057230 EP2012057230W WO2012146535A1 WO 2012146535 A1 WO2012146535 A1 WO 2012146535A1 EP 2012057230 W EP2012057230 W EP 2012057230W WO 2012146535 A1 WO2012146535 A1 WO 2012146535A1
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Maximilian Dochnahl
Joachim Gebhardt
Michael Keil
Michael Rack
Uwe Josef Vogelbacher
Roland Götz
Rainer Noack
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Basf Se
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/06Heterocyclic 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 carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/14Heterocyclic 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 three or more hetero rings

Definitions

  • the present invention relates to a process for preparing 2-substituted 2,4-dihydro- [1 ,2,4]triazole-3-thiones, in particular pesticidal compounds of this triazole class with phytopathogenic activity.
  • the invention also relates to specific intermediates that are obtained during the reaction sequence.
  • Important pesticidal compounds carry a mercapto-triazole group.
  • Specific thio-triazole compounds are known as active ingredients having pesticidal, in particular fungicidal activity, for example, from WO 96/38440 (A1 ).
  • WO 2009/077471 (A2), WO 2009/077443 (A2), WO 2009/077500 (A2), WO 2009/077497 (A2), EP 09178224 (A1 ), EP 09178291 (A1 ), E P 09178288 (A1 ) describe further specific mercapto-triazole compounds and provide routes for the preparation of disclosed compounds.
  • prepa ration of such 2,4-dihydro-[1 ,2,4]triazole-3-thione derivatives is often cumbersome and not high yielding.
  • DE 19744401 (A1 ) describes the process for the preparation of certain 2-substituted 2,4-dihydro-[1 ,2,4]triazole-3-thiones using a hydrazine derivative with a carbonyl compound and thiocyanate to provide an intermediate triazolidinethione which is, in a second step, treated with formic acid to provide the corresponding 2,4-dihydro- [1 ,2,4]triazole-3-thiones.
  • the mercapto-triazole groups of the general formula (III) can be present in two tautomeric forms - the "thiol” form of the formula (Ilia) or in the "thiono” form of the formula (1Mb).
  • the disulfide (VII) is formed and can thus be produced in a directed synthesis.
  • This approach provides several advantages, as the disulfides of the formula (VI I) are obtained in yields that are greater than 80% without residual starting material and with very limited amounts of desulfurized compounds of the formula (VI).
  • disulfides of formula (VII) can be reduced to provide corresponding compounds of the formula (II I) in a subsequent reduction step using methods that are well known to the skilled person.
  • Disulfides of the formula (VII) are known to possess microbicidal activity and a process for their preparation by way of oxidation of 2,4-dihydro-[1 ,2,4]triazole-3-thiones has been described in WO 97/43269 (A1 ).
  • this process as it starts from thiono- triazoles, suffers from the disadvantages associated with the preparation of the starting material, as pointed out above.
  • one aspect of the present invention is a process for the preparation of 2- substituted 2,4-dihydro-[1 ,2,4]triazole-3-thiones of the formula (III) wherein is a group (1 )
  • # shall mean the point of attachment to the triazolo group, and A and B are defined as follows:
  • a or B is a three-, four-, five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated heterocycle or five-, six-, seven-, eight-, nine- or ten- membered aromatic heterocycle, where the heterocycle contains in each case one, two, three or four heteroatoms from the group consisting of O, N and S; is naphthyl or phenyl; and the respective other variable B or A has one of the meanings mentioned above for A or B or is Ci-Cs-alkyl, Ci-Cs-haloalkyl, C2-C8-alkenyl, C2-C8- haloalkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, or benzodioxolyl; where A and/or B independently of one another are unsubstituted or
  • L is halogen, cyano, nitro, cyanato (OCN), Ci-Cs-alkyl, Ci-Cs-haloalkyl, phenyl-Ci-C6-alkyloxy, C2-Cs-alkenyl, C2-C8-haloalkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, C4-Cio-alkadienyl, C4-Cio-haloalkadienyl, Ci-Cs-alk- oxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylcarbonyloxy, Ci-Cs-alkylsulfonyloxy, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8-alkynyloxy, C2-C8- haloalkynyloxy, Cs-Cs-cycloalkyl, Cs-Cs-hal
  • a 5 , A 6 independently of one another are hydrogen, Ci-Cs-alkyl,
  • Ci-Cs-haloalkyl C2-Cs-alkenyl , C2-C8-haloalkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-C8- cycloalkenyl or C3-Cs-halocycloalkenyl; where the aliphatic and/or alicyclic and/or aromatic groups of the radical definitions of L for their part may carry one, two, three or four identical or different groups R L : is halogen, cyano, nitro, Ci-Cs-alkyl, Ci-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Cs-Cs-cycloalkyl , C3-Cs-halocycloal kyl , C3-C8- cycloalkenyl, C3
  • R 11 and R 22 have the following meanings:
  • R 11 , R 22 independently of one another Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl or phenyl, wherein the alkyl, cycloalkyl and phenyl moieties may be unsubstituted or substituted by one, two, three or four substituents L; or
  • R 11 and R 22 together with the carbon atom to which they are attached, form a five- or six-membered saturated or partially unsaturated ring, that can be unsubstituted or substituted by one, two, three, four or five substituents L', wherein L' stands for L as defined above or stands for a group wherein R 33 and R 44 independently are selected from the group of hydrogen and the meaning for L as defined above. is a group (3)
  • phenyl-Ci-Cs-alkyI phenyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S; where the aliphatic and/or aromatic and/or heterocyclic groups for their part may carry one, two, three or four identical or different groups selected from halogen, cyano, nitro, Ci-Cs-alkyl, Ci-Cs-haloalkyl, d-Cs-alkoxy, Ci-Cs- haloalkoxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkenyl, C3-C8-cycloalkoxy, Cs-Cs-halocycloalkoxy, d-Cs-alkylcarbonyl, d-Cs- alkylcarbonyloxy, d-Cs-alk
  • R is defined as above by treatment with inorganic nitrites and an acid or in the presence of organic nitrites in an organic solvent or water or mixtures thereof giving the corresponding compound of formula (VIII).
  • R is defined as above and is an anion selected from fluoride, chloride, bromide, iodide, arylsulfonate, alkylsulfonate, haloalkylsulfonate or X 01 OSO 3 , in which X 01 is CrC 8 -alkyl, Ci-C 8 -haloalkyl or C 3 -C 8 -cycloalkyl where above mentioned alkyl, haloalkyl or aryl groups are unsubstituted or substituted by one, two, three or four independently selected inert substituents sulfate, sulfonate, phosphate, phosponate, tetrafluoroborate, tetraphenylborate, hexafluorophosphate, hexafluoroarsenate, hexafluoroantimonate, trifluoroacetate, trichloroace- tate, perchlorate, Ci-Cio-al
  • R is defined as above, by means of a reducing agent; iii) treating the reaction mixture with a reducing reagent suitable to cleave disulfide groups.
  • the present invention also relates to a process for the deamination of compounds of the formula (I) by way of conducting step i), step ii) and step iii) in one vessel (one-pot procedure) with successive addition of reagents or solvents.
  • the diazotation of an aromatic amine and replacement of the diazo group by hydrogen is well known to the skilled person and can be achieved as previously described in prior art (Organic Reactions 1944, 2, 262; Organic Reactions 1953, 7, 263; Comprehensive Organic Synthesis 1991 , 8, 81 1 ).
  • One suitable way is to treat compounds of the for- mula (I) with inorganic nitrites or organic nitrites.
  • Suitable inorganic nitrites can be, for example, alkali metal nitrites or alkaline earth metal nitrites. According to one embodiment of the present invention preferably sodium nitrite and potassium nitrite are used.
  • Ci-Cio-alkylnitrites for example n-butyl nitrite, iso-butyl nitrite, tert-butyl nitrite and isoamyl nitrite are preferred.
  • the diazotation step i) with inorganic nitrites requires the addition of an acid, preferably a strong acid such as hydrochloric acid, sulfuric acid, phosphoric acid or hypophos- phoric acid.
  • an acid preferably a strong acid such as hydrochloric acid, sulfuric acid, phosphoric acid or hypophos- phoric acid.
  • the reaction is carried out at temperatures from -10 to 60 °C, according to a preferred embodiment of the invention the reaction is carried out at temperatures from 0 to 30 °C.
  • the diazotation step i) with organic nitrites is preferably carried out at temperatures from 0 to 60°C, according to a preferred embodiment of the invention the reaction is carried out at temperatures from 10 to 40°C.
  • Suitable reducing agents in step ii) are, for example, Ci-Cio-alkanols such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, 2-butanol, iso-butanol, pentanol, 2-ethyl- hexanol or formic acid and its salts such as ammonium formate, esters of C1-C4- alkanoles with formic acid, formic amides such as formamide or mercaptanes or alka- line metal borohydrides or tin(ll) salts, phosphonic acid, hypophosponic acid can be used.
  • Ci-Cio-alkanols such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, 2-butanol, iso-butanol, pentanol, 2-ethyl- hexanol
  • reaction components in carrying out the diazotation of compounds of the formula (I) are usually employed in amounts such that 1 to 10 moles, in particular 1 to 3, more particularly 1 to 2 moles of inorganic nitrite are used per mole of the compound (I) while at least the same amount of reducing agent is added with the inorganic nitrite. It may be preferred if 1 to 1 .5 moles of inorganic nitrite are used per mole of the compound (I) while the same amount of reducing agent is added with the inorganic nitrite.
  • Another preferred embodiment of the present invention is that 1 to 5 moles of alkyl nitrite are used per mole of the compound (I). Still another preferred embodiment of the present invention is if 1 to 2 moles of alkyl nitrite are used per mole of the compound (I)-
  • Another embodiment of the present invention is that, when using an inorganic nitrite for the diazotation, 0.1 to 1 moles of a strong acid are used per mole of the compound (I). Still another preferred embodiment of the present invention is if 0.5 to 1 moles of a strong acid are used per mole of the compound (I).
  • Solvents that can be employed in such diazotation/reduction sequences provide ap- intestinal solubility of the starting materials, i.e. compounds of the formula (I), and are also suitable to at least partially dissolve the nitrite and/or the reducing agent.
  • the starting materials i.e. compounds of the formula (I)
  • the reducing agent preferably water or aqueous mixtures of water soluble solvents can be used.
  • Ci-C6-alkanols such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, 2-butanol, iso-butanol, tert-butanol, n- pentanol and 2-ethylhexanol or dimethyl sulfoxide, ⁇ , ⁇ -dimethylformamide, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone or cyclic ethers such as dioxane and tetrahydrofuran, 2-methyltetrahydrofuran, or nitriles such as acetonitrile and propionitrile or ketones, for example di-Ci-C6-alkyl ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone are examples of such solvents
  • the present invention relates to solvents in the diazotation/reduction sequences that are water or protic solvents or mixtures of water and protic solvents.
  • the present invention relates to solvents in the diazotation/reduction sequences that are water, n-butanol, iso-butanol, tert-butanol, tetrahydrofuran and toluene.
  • the present invention relates to solvents in the diazotation/reduction sequences that are water, n-butanol, iso-butanol or tert- butanol,. According to another preferred embodiment the present invention relates to tetrahydrofuran as solvent in the diazotation/reduction sequences.
  • the present invention relates to solvents in the diazotation/reduction sequences that are water or toluene.
  • the present invention relates to solvents in the diazotation/reduction sequences that are iso-butanol or n-butanol.
  • suitable counterions Y _ of said dia- zonium compounds of the formula (VIII) are halides, for example chloride, bromide, iodide or arylsulfonates, for example benzenesulfonate, p-tolylsulfonate, 2- nitrophenylsulfonate, 4-nitrophenylsulfonate, 4-bromophenylsulfonate or alkylsul- fonates, for example methanesulfonate or haloalkylsulfonates, for example trifluoro- methylsulfonate, nonafluorobutylsulfonate or alkyl- and haloalkylsulfates, for example methylsulfate where above mentioned alkyl,
  • the counterion Y- is an an- ion selected from fluoride, chloride, bromide, sulfate, sulfonate, phosphate, phosponate, tetrafluoroborate, tetraphenylborate, hexafluorophosphate, hexafluoroarsenate, hexafluoroantimonate.
  • the counterion Y- is an anion selected from Ci-Cio-alkoxide or hydroxide.
  • the duration of diazotation reactions as described in step i) of the process is between 5 and 60 minutes and is accompanied by the formation of IS O-gas.
  • the reducing agent of step (iii) is preferably selected from the group comprising alkali metal or alkaline earth metal dithionite, alkali metal formate, sulfur dioxide, hydrazine, zinc/ammonium chloride, alkali metal alanate, tin(ll) salts or mixtures thereof.
  • the use of sodium dithionite is particularly preferred.
  • 2-substituted 2,4-dihydro-[1 ,2,4]triazole-3-thiones of the formula (III) usually precipitate from concentrated solutions and the product can be separated from the reaction mixture by filtration. Purification of thus obtained material can be achieved by washing of the precipitate and/or recrystallization.
  • novel compounds according to the invention contain chiral centers and are generally obtained in the form of racemates or as diastereomeric mixtures of erythro and threo forms.
  • the erythro and threo diastereomers of the compounds according to the invention can be separated and isolated in pure form, for example, on the basis of their different solubilities or by column chromatography. Using known methods, such uniform pairs of diastereomers can be used to obtain uniform enantiomers.
  • the invention provides both the pure enantiomers or diastereomers and mixtures thereof.
  • the scope of the present invention includes in particular the (R) and (S) isomers and the racemates of the compounds according to the invention, which have centers of chirality.
  • Suitable compounds according to the invention also include all possible stereoisomers (cis/trans isomers) and mixtures thereof.
  • the compounds according to the invention may be present in various crystal modifications. They are likewise provided by the present invention.
  • the reactants used contain chiral centers and are generally used in the form of racemates or as diastereomeric mixtures of erythro and threo forms.
  • the erythro and threo diastereomers of these compounds can be separated and isolated in pure form, for example, on the basis of their different solubilities or by column chromatography. Using known methods, such uniform pairs of diastereomers can be used to obtain uniform enantiomers.
  • the invention provides both the use of pure enantiomers or diastereomers and mixtures thereof.
  • the scope of the present invention includes in particular the use of the (R) and (S) isomers and the racemates of the rspective reactants, which have centers of chirality.
  • Suitable compounds used according to the invention also include all possible stereoisomers (cis/trans isomers) and mixtures thereof.
  • the compounds used according to the invention may be present in various crystal modifications. They are likewise possible to be used in the inventive process.
  • 4-Amino-2,4-dihydro-[1 ,2,4]triazole-3-thione compounds of the formula (I) can be prepared as described in an application that was filed on the same day as the present application.
  • the present invention also relates to a process for the preparation of compounds of the formula (III) by way of an alkylation/thiolation sequentce to provide compounds of the formula (I) as set forth in the application mentioned above, followed by the diazotation/reduction sequence as described above, comprising step i), step ii) and step iii). All steps are conducted in one vessel (one-pot procedure) with successive addition of reagents or solvents.
  • halogen fluorine, chlorine, bromine and iodine
  • alkyl and the alkyl moieties of composite groups such as, for example, alkylamino: saturated straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 12 carbon atoms, for example Ci-C6-alkyl, such as methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-me- thylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpent
  • haloalkyi alkyl as mentioned above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above; in particular C1-C2- haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2- dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1 ,
  • unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one double bond in any position.
  • small alkenyl groups such as (C2-C4)-alkenyl
  • larger alkenyl groups such as (C5-C8)-alkenyl.
  • alkenyl groups are, for example, C2-C6-alkenyl, such as ethenyl, 1 - propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 - propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-1 - butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 -methyl-3- butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1 -dimethyl-2-propenyl, 1 ,2-di
  • halocycloalkenyl cycloalkenyl as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine; alkoxy: an alkyl group as defined above which is attached via an oxygen, preferably having 1 to 8, more preferably 2 to 6, carbon atoms.
  • Examples are: methoxy, ethoxy, n- propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy or 1 ,1 - dimethylethoxy, and also for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 - ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4- methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -
  • Examples are OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoro- methoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2- difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2- fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2- chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3- bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,
  • alkylene divalent unbranched chains of CH2 groups. Preference is given to (C1-C6)- alkylene, more preference to (C2-C4)-alkylene; furthermore, it may be preferred to use (Ci-C3)-alkylene groups.
  • alkylene radicals are CH2, CH2CH2, CH2CH2CH2, CH 2 (CH 2 )2CH2, CH 2 (CH 2 )3CH 2 and CH 2 (CH 2 )4CH 2 ; a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle which contains 1 , 2, 3 or 4 heteroatoms from the group consisting of O, N and S, where the heterocycle in question may be attached via a carbon atom or, if present, via a nitrogen atom. According to the invention, it may be preferred for the heterocycle in question to be attached via carbon, on the other hand, it may also be preferred for the heterocycle to be attached via nitrogen.
  • heterocyclyl a three- or four-membered saturated heterocycle which contains one or two heteroatoms from the group consisting of O, N and S as ring members
  • heterocyclyl a five- or six-membered saturated or partially unsaturated heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S as ring members: for example monocyclic saturated or partially
  • unsaturated heterocycles which, in addition to carbon ring members, contain one, two or three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3- isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4- isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5- thiazolidinyl, 2-imidazolidinyl, 4-
  • the heterocycle in question may be attached via a carbon atom or, if present, via a nitrogen atom. According to the invention, it may be preferred for the heterocycle in question to be attached via carbon, on the other hand, it may also be preferred for the heterocycle to be attached via nitrogen.
  • the heterocycle is in particular: a 5-membered heteroaryl which contains one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and/or one sulfur or oxygen atom, where the heteroaryl may be attached via carbon or nitrogen, if present: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one, two or three nitrogen atoms and/or one sulfur or oxygen atom as ring members, for example furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1 ,2,3-; 1 ,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1 ,3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, in particular 2-furyl, 3-furyl, 2-thienyl, 3- thienyl, 2-pyrrolyl,
  • 6-membered heteroaryl which contains one, two, three or four, preferably one, two or three, nitrogen atoms, where the heteroaryl may be attached via carbon or nitrogen, if present: 6-ring heteroaryl groups which, in addition to carbon atoms, may contain one to four or one, two or three nitrogen atoms as ring members, for example pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1 ,2,3-triazinyl, 1 ,2,4-triazinyl, 1 ,3,5-triazinyl, in particular 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl
  • optionally substituted heterocycle a saturated heterocycle which is bonded via a ring nitrogen atom and has 5, 6, 7 or 8 ring atoms, where, as well as the nitrogen atom, the ring atoms also further which is unsubstituted or bears 1 , 2, 3, 4 or 5 and especially 1 , 2 or 3 substituents which are inert under the conditions of the reaction.
  • inert substituents are CN, Ci-C6-alkyl, Ci-C6-alkylthio, Ci-C6-alkylsulfonyl, C1-C4- haloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, and Ci-C4-alkoxy-Ci-C6-alkyl.
  • the heterocycle may, as well as the nitrogen atom in position 1 and the ring carbon atoms, also comprise 1 or 2 further heteroatoms selected from N, O and S as ring atoms.
  • N-bonded, 5- to 8-membered, saturated, optionally substituted heterocycles are pyr- rolidin-1 -yl, piperdin-1 -yl, morpholin-4-yl, piperazin-1 -yl and N-methylpiperazin-1 -yl; alkylthio: alkyl as defined above which is attached via an S atom; amino: NR 1N R 2N group, in which R 1N and R 2N can be alkyl, aryl or heteroaryl as defined above, which is attached via an N atom alkylamino: alkyl as defined above which is attached via N atom; haloalkylthio: haloalkyl as defined above which is attached via an S atom; hydroxy: OH group which is attached via an O atom; carbonitrile: CN group which is attached via an C atom; aldehyde: CHO group, which is attached via an C atom; carboxylic ester: COOR 10 group, in which R 1 °
  • R can be in principle any group (1 ), (2) or (3) as defined above that allows carrying out the reaction steps according to the inventive process. If necessary, some reactive groups within the group R can be protected via suitable protecting groups. It is within the skill of a person of the art to choose suitable groups and it is general knowledge of the skilled person how to insert and remove such groups.
  • the group R in the compounds (III) and precurors thereof carries an epoxide group.
  • R is a group of the formula (1 ) as define above.
  • a and B independently are unsubstituted phenyl or sub- stituted phenyl containing one, two, three or four independently selected substituents L.
  • A is unsubstituted phenyl.
  • A is phenyl, containing one, two, three or four, in particular one or two, independently selected substituents L, wherein L is as defined or as preferably defined herein.
  • one of the substituents is in 4-position (para) of the phenyl ring.
  • L is in each case independently selected from F, CI, Br, nitro, phenyl, phenoxy, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoro- methyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and trifluorochloro- methyl.
  • L is in each case independently selected from F, CI and Br, in particular F and CI.
  • A is monosubstituted phenyl, containing one sub- stituent L, wherein L is as defined or as preferably defined herein. According to one aspect, said substituent is in para-position.
  • A is 3-fluorophenyl. According to another embodiment, A is phenyl, containing two or three independently selected substituents L.
  • A is phenyl which is substituted by one F and contains a further substituent L, where the phenyl may additionally contain one or two substituents L selected independently of one another, wherein L is as defined or preferably defined herein.
  • A is a group A-1
  • # is the point of attachment of the phenyl ring to the oxirane ring
  • L 2 is selected from the group consisting of F, CI , NO2, phenyl, halogenphenyl, phenoxy, halogenphenoxy, Ci-C4-al kyl , Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy and Ci-C4-haloalkylthio;
  • L 3 is independently selected from the group consisting of F, CI, Br, NO2, phenyl, halogenphenyl, phenoxy, halogenphenoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio; and
  • L 2 is selected from the group consisting of F, CI, methyl, methoxy, CF3, CHF2, OCF3, OCF3 and OCHF2. According to a more specific embodiment, L 2 is F or CI.
  • L 3 is independently selected from the group consisting of F, CI, methyl, methoxy, CF3, CH F2, OCF3, OCF3 or OCHF2. According to a more specific embodiment, L 3 is independently F or CI.
  • the fluorine substituent is, according to a preferred embodiment, in the 4-position.
  • A is disubstituted phenyl, containing exactly two substituents L that are independently selected from each other, wherein L is as defined or as preferably defined herein.
  • L is in each case independently selected from F, CI, Br, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, in particular selected from F, CI, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, in particular selected from F, CI, methyl, trifluoromethyl and methoxy.
  • the second substituent L is selected from methyl, methoxy and chloro.
  • one of the substituents is in the 4-position of the phenyl ring.
  • A is phenyl containing one F and exactly one further substituent L as defined or preferably defined herein.
  • A is disubstituted phenyl which contains one F and a further substituent L selected from the group consisting of CI, C1-C4- alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, in particular selected from the group consisting of CI, methyl, trifluoromethyl and methoxy.
  • the second substituent L is specifically selected from the group consisting of methyl, methoxy and chlorine.
  • one of the substituents is located in the 4-position of the phenyl ring.
  • A is 2,4-disubstituted phenyl.
  • A is 2,3-disubstituted phenyl.
  • A is 2,5-disubstituted phenyl.
  • A is 2,6-disubstituted phenyl.
  • A is 3,4-disubstituted phenyl.
  • A is 3,5-disubstituted phenyl.
  • A is phenyl which is substituted by exactly two F.
  • A is 2,3-difluoro-substituted.
  • A is 2,4-difluoro-substituted.
  • A is 2,5-difluoro-substituted.
  • A is 2,6-difluoro- substituted.
  • A is 3,4-difluoro-substituted.
  • A is 3,5-difluoro-substituted.
  • A is trisubstituted phenyl containing exactly three independently selected substituents L, wherein L is as defined or preferably defined herein.
  • A is phenyl which is substituted by exactly three F.
  • A is 2,3,4-trisubstituted, in particular 2,3,4- trifluoro-substituted.
  • A is 2,3,5-trisubstituted, in particular 2,3,5-trifluoro-substituted.
  • A is 2,3,6-trisubstituted, in particular 2,3, 6-trifluoro-substituted.
  • A is 2 ,4,6- trisubstituted, in particular 2,4, 6-trifluoro-substituted.
  • A is 3,4,5-trisubstituted, in particular 3,4,5-trifluoro-substituted.
  • A is 2,4,5-trisubstituted, in particular 2, 4, 5-trifluoro-substituted.
  • B is phenyl, that is unsubstituted or phenyl which contains one, two, three or four independently selected substituents L, wherein L is as defined or preferably defined herein. According to one embodiment of the invention, B is unsubstituted phenyl.
  • B is phenyl which contains one, two, three or four independently selected substituents L, wherein L is as defined or preferably defined herein.
  • B is phenyl which contains one, two or three, preferably one or two, independently selected substituents L, wherein L is as defined or preferably defined herein.
  • L is i n each case independently selected from F, CI, Br, methyl, methoxy and trifluoromethyl.
  • B is phenyl, which contains one, two or three, preferably, one or two, halogen substituents.
  • B is phenyl which contains one, two, three or four substituents L, wherein L is independently selected from F, CI, Br, methyl, ethyl, iso- propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, di- fluorochloromethyl, trifluoromethoxy, difluoromethoxy and difluorochloromethyl.
  • L is in each case independently selected from F, CI and Br.
  • B is unsubstituted phenyl or phenyl which contains one, two or three substituents independently selected from halogen, NO2, amino, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylamino, Ci-C4-dialkylamino, thio and Ci-C4-alkylthio.
  • B is a phenyl ring that is monosubstituted by one substituent L, where according to a special aspect of this embodiment, L is located in the ortho-position to the point of attachment of the phenyl ring to the oxirane ring.
  • L is as defined or preferably defined herein.
  • B is monochloro-substituted phenyl, in particular 2- chlorophenyl.
  • B is phenyl, which contains two or three, in particular two, independently selected substituents L, wherein L is as defined or preferably defined herein.
  • B is a phenyl ring which contains a substituent L in the ortho-position and furthermore has one further independently selected substituent L.
  • the phenyl ring is 2,3-disubstituted.
  • the phenyl ring is 2,4-disubstituted.
  • the phenyl ring is 2,5-disubstituted.
  • the phenyl ring is 2,6-disubstituted.
  • B is a phenyl ring which contains a substituent L in the ortho-position and furthermore contains two further independently selected substituents L.
  • the phenyl ring is 2,3,5-trisubstituted.
  • the phenyl ring is 2,3,4-trisubstituted.
  • the phenyl ring is 2,4,5-trisubstituted.
  • B is phenyl which contains one substituent L in the 2-position and one, two or three further independently selected substituents L.
  • B is a group B-1
  • L 1 is selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio, preferably selected from the group consisting of F, CI, methyl, ethyl, methoxy, ethoxy, CF3, CH F2, OCF3,
  • L 2 is selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio, preferably selected from the group consisting of F, CI, methyl, ethyl, methoxy, ethoxy, CF3, CH F2, OCF3,
  • L 3 is independently selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-ha l oa l kyl , Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio, preferably selected from the group consisting of F, CI, methyl, ethyl, methoxy, ethoxy, CF 3 , CHF 2 , OCF 3 , OCHF 2 and SCF 3 ; and
  • n 0, 1 or 2.
  • L 1 is F. According to another preferred embodiment, L 1 is CI. According to a further preferred embodiment, L 1 is methyl. According to yet a further preferred embodiment, L 1 is methoxy. According to yet a further preferred embodiment, L 1 is CF3. According to yet a further preferred embodiment, L 1 is OCF3 or OCHF2. According to a preferred embodiment, in the compounds of the formula I according to the invention, B is thus phenyl which contains a substituent selected from the group consisting of F, CI, CH3, OCH3, CF3, CHF2, OCF3 and OCHF2 in the 2-position and one or two further independently selected substituents L.
  • L 2 is F. According to another preferred embodiment, L 2 is CI . According to a further preferred embodiment, L 2 is methyl. According to yet a further preferred embodiment, L 2 is methoxy. According to yet a further preferred embodiment, L 2 is CF3. Accord i ng to yet a further preferred embodiment, L 2 is OCF 3 or OCHF 2 .
  • L 3 is F. According to another preferred embodiment, L 3 is CI. According to a further preferred embodiment, L 3 is methyl. According to yet a further preferred embodiment, L 3 is methoxy. According to yet a further preferred embodiment, L 3 is CF3. Accord i ng to yet a further preferred embodiment, L 3 is OCF 3 or OCHF 2 .
  • m 0; i.e. B is a disubstituted phenyl ring.
  • B is a 2,3-disubstituted phenyl ring.
  • the pheny ring B is 2,4-disubstituted.
  • the phenyl ring B is 2,5-disubstituted.
  • the phenyl ring is 2,6-disubstituted.
  • m 1 ; i.e. B is a trisubstituted phenyl ring.
  • the phenyl ring B is 2,3,5-trisubstituted. According to another preferred further aspect, the phenyl ring B is 2,3,4-trisubstituted. According to yet a further preferred embodiment, the phenyl ring B is 2,4,5- trisubstituted.
  • a 1 is hydrogen, hydroxy, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl
  • a 2 is one of the groups mentioned under A 1 or Ci-C 4 -alkoxy, Ci-C 4 - haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkoxy or C3-C6-halocycloalkoxy;
  • a 5 ,A 6 independently of one another are hydrogen, Ci-C 4 -alkyl, Ci-C 4 -halo- alkyl; where the aliphatic and/or alicyclic groups of the radical definitions of L for their part may carry one, two, three or four identical or different groups R L :
  • R L is halogen, cyano, nitro, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, amino, Ci-Cs- alkylamino, di-Ci-Cs-alkylamino.
  • L is independently selected from the group consisting of halogen, NO2, amino, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci- C 4 -alkylamino, di-Ci-C 4 -alkylamino, thio and Ci-C 4 -alkylthio.
  • L is independently selected from the group consisting of halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and C1-C4- haloalkylthio, in particular halogen, Ci-C 4 -alkyl and Ci-C 4 -haloalkyl.
  • L is independently selected from the group consisting of F, CI, Br, CH 3 , C 2 H 5 , i-C 3 H 7 , t-C 4 H 9 , OCH 3 , OC2H5, CF 3 , CCI 3 , CHF2, CCIF2, OCF3, OCHF2 and SCF3, in particular selected from the group consisting of F, CI, CH 3 , C2H5, OCH3, OC2H5, CF 3 , CHF 2 , OCF3, OCH F2 and SCF 3 .
  • L is independently selected from the group consisting of F, CI, CH3, OCH3, CF3, OCF3 and OCHF2. It may be preferred for L to be independently F or CI.
  • a and B are as defined as follows:
  • a phenyl which is unsubstituted or substituted by one, two or three substituents L that may be the same or different, independently selected from F, CI, Br, nitro, phenyl, phenoxy, methyl, ethyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, di- fluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and trifluoro- methylthio; and
  • B phenyl that is substituted by one, two or three substituents L that may be the same or different, independently selected from F, CI, Br, methyl, ethyl, iso-propyl, tert- butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloro- methyl, trifluoromethoxy, difluoromethoxy and trifluoromethylthio.
  • A is 4- flourphenyl and B is 2-chlorophenyl.
  • A is 4-fluorophenyl and B is 2-difluoromethoxyphenyl.
  • a i s ph enyl 4-chlorophenyl, 2,4-chlorophenyl, 2-chlorophenyl, 2-fluorophenyl, 4- methylphenyl, 4-fluorophenyl, 3-bromo-4-fluorophenyl, 4-bromophenyl, 3,4- dichlorophenyl, 4-tert-butyl-phenyl, 3-chlorophenyl, 3,5-dichlorophenyl or 4- trifluoromethoxyphenyl, and B is 2-fluorophenyl.
  • A is 2,4-difluorophenyl and B is 2-chlorophenyl.
  • A is 3,4-difluorophenyl and B is 2-chlorophenyl.
  • A is 2,4-difluorophenyl and B is 2-fluorophenyl.
  • A is 3,4-difluorophenyl and B is 2-fluorophenyl.
  • A is 2,4-difluorophenyl and B is 2-trifluoromethylphenyl.
  • A is 3,4-difluorophenyl and B is 2-trifluoromethylphenyl.
  • A is 3,4-difluorophenyl and B is 2-methylphenyl
  • a and B are defined as follows:
  • A is phenyl and B is 2,4-dichlorophenyl.
  • A is phenyl and B is 2-fluoro-3-chlorophenyl.
  • A is phenyl and B is 2,3,4-trichlorophenyl.
  • A is 4-fluorophenyl and B is 2,4-dichlorophenyl.
  • A is 4-fluorophenyl and B is 2-fluoro-3-chlorophenyl.
  • A is 4-fluorophenyl and B is 2,3,4-trichlorophenyl.
  • A is 2-chlorophenyl and B is 2,4-dichlorophenyl.
  • A is 2-chlorophenyl and B is 2-fluoro-3-chlorophenyl.
  • A is 2-chlorophenyl and B is 2,3,4-trichlorophenyl.
  • the pure enantiomers or a mixture of enantiomers (racemic or enantiomerically enriched) of the reactants, in particular of compounds of the formula (I), can be used.
  • the following different stereoisomers of compounds (l)-(1 ) can be employed in the inventive process: compound (l)-(1 )-a1 ):
  • the organic group R in the compounds (III) and precursors thereof carries a free hydroxy group and compounds (III) are from the triazole class of fungicides.
  • R is a group of the formula (2) as defined above.
  • R 11 and R 22 in the group of formula (2) are preferably independently selected from Ci-C4-alkyl and phenyl , wherein the alkyl and phenyl group independently may contain one, two, three or four substituents , independently selected from F, CI, Br, methoxy, ethoxy, propoxy, isopropoxy, Ci-C2-alkoximino, cy- clopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl.
  • R 11 stands for C1-C4- alkyl that is substituted by one or two substituents independently selected from F, CI, methoxy, cyclopropyl, cyclopentyl and/or cyclohexyl and R 22 stands for phenyl, that is substituted by one, two, three or four substituents independently selected from F, CI, Br and methoxy.
  • R 11 is 1 -ethyl that is 1 -substituted by cyclopropyl and R 22 is 4-chlorophenyl.
  • R 11 is n- butyl and R 22 is 2,4-dichlorophenyl.
  • R 11 and R 22 are preferably independently selected from Ci-C4-alkyl, phenyl-Ci-C4-alkyl and C3-C6-cycloalkyl, preferably phenyl-Ci-C4-alkyl and C3-C6-cycloalkyl, wherein the alkyl, phenyl and cycloalkyl groups independently may contain one, two, three or four substituents , independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl and/or tert-butyl.
  • R 11 stands for phenyl- Ci-C4-alkyl that is substituted in the phenyl moiety by one, two, three or four substitu- ents independently selected from F, CI and methoxy and R 22 stands for C3-C6- cycloalkyl, that is substituted by one, two, three or four substituents independently selected from F , C I , Br a nd methoxy.
  • I n one specifi c em bod i ment
  • R 11 is 2- chlorophenylmethyl and R 22 is 1 -chlorocyclopropyl.
  • R 11 and R 22 are preferably independently selected from Ci-C4-alkyl and phenyl-Ci-C4-alkyl, wherein the alkyl and phenyl groups may contain one, two, three or four substituents , independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoro- methyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxyvarbonyl, methoxyiminomethyl, 1 - methoximinoethyl and nitro.
  • substituents independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy
  • R 11 stands for Ci-C4-alkyl that may be substituted by one or two substituents, independently selected from methyl, ethyl, propyl, isopropyl and tert-butyl and R 22 stands for phenyl-Ci-C4-alkyl, that is substituted in the phenyl moiety by one, two, three or four substituents independently selected from F, CI, Br, CN, methyl, trifluoromethyl and methoxy.
  • R 11 is tert- butyl and R 22 is 2-(4-chlorophenyl)-1 -ethyl.
  • R 11 and R 22 are preferably independently se- lected from phenyl, wherein the phenyl moieties may contain one, two, three or four substituents , independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxyvarbonyl, methoxyiminomethyl, 1-methoximinoethyl and nitro.
  • substituents independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluorome
  • R 11 and R 22 independently stand for phenyl, that may contain one, two or three substituents , independently selected from F, CI and Br.
  • R 11 is 2-fluorophenyl and R 22 is 4-fluorophenyl.
  • R 11 and R 22 together with the carbon atom to which they are attached, form a five- or six-membered saturated ring, that can be unsubstituted or substituted by one, two or three substituents L', wherein L' stands for L as defined above or stands for a group
  • ently are selected from the group of hydrogen, Ci-C4-alkyl and phenyl, wherein the alkyl and phenyl groups may contain one, two, three or four substituents , independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy and nitro.
  • R 11 and R 22 together with the carbon atom to which they are attached, form a five-membered saturated ring, that is substituted by one, two or three substituents L', wherein L' stands for Ci-C4-alkyl or for a group wherein R 33 and R 44 independently are selected from the group of hydrogen, Ci-C4-alkyl and phenyl, wherein the alkyl and phenyl groups may contain one, two, three or four substituents , independently selected from F, CI, CN, methyl, isopro- pyl, tert-butyl and methoxy.
  • L' stands for Ci-C4-alkyl or for a group wherein R 33 and R 44 independently are selected from the group of hydrogen, Ci-C4-alkyl and phenyl, wherein the alkyl and phenyl groups may contain one, two, three or four substituents , independently selected from F, CI, CN, methyl, isopro- pyl,
  • R 11 and R 22 together with the carbon atom to which they are attached, form a five-membered saturated substituted in 5-position by two methyl groups and contains a group wherein R 33 is hydrogen and R 44 is 4-chlorophenyl in 2-position.
  • R 11 and R 22 together with the carbon atom to which they are attached, form a five- or six-membered saturated ring, that can be unsubstituted or substituted by one, two or three substituents, independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, methyl- thio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, di- fluoromethoxy, nitro, benzyl, wherein the phenyl moiety itself may contain on, two, three or four substituents, independently selected from F, CI, CN, methyl, isopropyl, tert-butyl and methoxy.
  • R 11 and R 22 together with the carbon atom to which they are attached, form a five-membered saturated ring, that is substituted in 5-position by two methyl groups and contains a 4-chlorobenzyl group in 2- position.
  • compounds (l)-(2) and the synthesis of precursors thereof see also WO 96/16048 (A1 ), WO 96/38423 (A1 ), E P 378953 (B1 ), EP 655443 (A2), DE 4030039 (A1 ), DE 3337937 (A), DE 3315681 (A1 ), US 4414210 (A).
  • R in the compounds (I II) and precursors thereof is a group of the formula (3) as defined above.
  • R 55 in a group of the formula (3) is phenyl that is unsubstituted or substituted by one, two, three or four substituents independently selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenoxy-Ci-C6-alkyl and halophenyloxy, and R 66 and R 77 are independently selected from hydrogen, methyl, ethyl, n-propyl and n-butyl.
  • R 55 is phenyl that contains one, two or three substituents independently selected from F, CI and halophenoxy, wherein the phenoxy moiety contains one or two halogen atoms selected from CI and F; and R 66 is hydrogen and R 77 is Ci-C 4 -alkyl.
  • R 55 is 4-(4-chlorophenoxy)-2- chlorophenyl, R 66 is hydrogen and R 77 is methyl.
  • R 55 is 2,4-dichlorophenyl, R 66 is hydrogen and R 77 is n-propyl.
  • Another aspect of the present invention is diazo compounds of the formula (VIII) in which R is a group of the formula (1), (2) or (3) as defined above.
  • R in compounds (VIII) is a group (1) as defined above, including the specific embodiments thereof.
  • Y is fluoride (Zl)-(1), chloride (Zll)-(1), bromide (Zlll)-(1), sulfate (ZIV)-(1), sulfonate (ZV)-(1), phosphate (ZVI)-(1), phosphonate (ZVII)-(1), tetrafluoroborate (ZVIII)- (1), tetraphenylborate (ZIX)-(1), hexafluorophosphate (ZX)-(1), hexafluoroarsenate (ZXI)-(1), hexafluoroantimonate (ZXII)-(1) according to the invention, wherein A is defined as in tables 1a to 257a in combination with residues B in rows 1 to 514 of table A below, are suitable for the synthesis of the respective fungicides of formula (111) and are obtained by the inventive process.
  • the groups mentioned for a substituent in the tables are furthermore per se, independently of the combination in which they are

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Abstract

Preparation of 2-substituted 2,4-dihydro-[1,2,4]triazole-3-thiones of the formula (III), comprising the steps i), diazotation of 2-substituted 4-amino-2,4-dihydro-[1,2,4]triazole- 3-thiones by treatment with inorganic nitrites and an acid or in the presence of organic nitrites in an organic solvent or water or mixtures thereof, giving the corresponding 4- diazo-2,4-dihydro-[1,2,4]triazole-3-thiones, and ii), reduction of the diazo intermediate to provide mixtures of compounds of the formula (III) and compounds of the formula (VII), by means of a reducing agent, followed by, iii), treating the reaction mixture with a reducing reagent suitable to cleave disulfide groups.

Description

Process for the preparation of 2-substituted 2,4-dihydro-[1 ,2,4]triazole-3-thiones
The present invention relates to a process for preparing 2-substituted 2,4-dihydro- [1 ,2,4]triazole-3-thiones, in particular pesticidal compounds of this triazole class with phytopathogenic activity. The invention also relates to specific intermediates that are obtained during the reaction sequence.
Important pesticidal compounds carry a mercapto-triazole group. Specific thio-triazole compounds are known as active ingredients having pesticidal, in particular fungicidal activity, for example, from WO 96/38440 (A1 ). Also WO 2009/077471 (A2), WO 2009/077443 (A2), WO 2009/077500 (A2), WO 2009/077497 (A2), EP 09178224 (A1 ), EP 09178291 (A1 ), E P 09178288 (A1 ) describe further specific mercapto-triazole compounds and provide routes for the preparation of disclosed compounds. However, prepa ration of such 2,4-dihydro-[1 ,2,4]triazole-3-thione derivatives is often cumbersome and not high yielding.
In particular it is known to introduce the thio-group into triazole compounds using a strong base such as n-BuLi and sulfur powder. Alternatively triazole compounds are heated with sulfur in the presence of an aprotic polar solvent, such as, for example, Ν,Ν-dimethylformamide. S e e a l s o W O 99/19307 (A1 ), WO 97/06151 (A1 ), WO 97/051 19 (A1 ) and WO 96/41804 (A1 ). The disadvantages of these methods are that the yield of the desired products is often not satisfying, high amounts of side products are produced and that the reaction conditions often do not allow for the application on technical scales. Regarding the reaction using n-BuLi, a further disadvantage is that the reagent is quite expensive and that the reaction has to be carried out at very low temperatures, which necessitates special cooling equipment. Upscales are thus elaborate and expensive.
DE 19744401 (A1 ) describes the process for the preparation of certain 2-substituted 2,4-dihydro-[1 ,2,4]triazole-3-thiones using a hydrazine derivative with a carbonyl compound and thiocyanate to provide an intermediate triazolidinethione which is, in a second step, treated with formic acid to provide the corresponding 2,4-dihydro- [1 ,2,4]triazole-3-thiones. In analogy to this transformation DE 19839688 (A1 ) describes the reaction of a hydrazine derivative with formaldehyde und thiocyanate to give an intermediate triazolidinethione, which can be reacted with formic acid or an oxidizing agent to give corresponding 2,4-dihydro-[1 ,2,4]triazole-3-thione derivatives.
This type of process suffers from the disadvantage that hydrazine derivatives are often not readily available. Moreover yields of the transformations are low. An a lternative synth eti c route to o bta i n 2-substituted 4-amino-2,4-dihydro- [1 ,2,4]triazole-3-thiones compounds is described in the literature (H. G. O. Becker, D. Nagel , H .-J. Timpe J. Prakt. Chem. 1973, 315, 9 7-105) where thiolation of corresponding amino-triazolium salts is carried out by way of treatment with sulfur in the presence of triethylamine in pyridine as the solvent. The same procedure is described for the thiolation of analog structural isomers, 4-substituted 1 -amino-1 ,2,4- triazolthiones by G . La u s a n d W. Klotzer in Synthesis 1990, 707-717. The disadvantages of the protocol are moderate yields and long reaction times. Moreover pyridine is an expensive and toxic solvent and therefore poses risks to the environment and is problematic with regards to worker exposure. Since pyridine has a low vapor pressure (18 mm Hg), and its flash point of 21 °C implies that it can be ignited under almost all ambient temperature conditions, it is not a suitable solvent to be used in industrial scale production processes.
The methods known from the prior art for the efficient synthesis of substituted thiono- triazoles are disadvantageous because the yields are insufficient and/or the reaction conditions and parameters such as temperature and/or reactants are not suitable for the industrial scale.
It is therefore an objective of the present invention to provide an efficient process for the preparation of 2,4-dihydro-[1 ,2,4]triazole-3-thiones of the formula (III), which affords the desired compounds with high yields and is suitable for the industrial scale.
Compounds of the formula (III) have an enormous economic significance as fungicidal^ active compounds. For these reasons, inter alia, there is an ongoing need for improved processes that easily make the mercapto-triazole compounds available.
Figure imgf000003_0001
The mercapto-triazole groups of the general formula (III) can be present in two tautomeric forms - the "thiol" form of the formula (Ilia) or in the "thiono" form of the formula (1Mb).
In search of an efficient process to prepare compounds of the formula (I II) a general protocol for their preparation has now surprisingly been found by way of treating 2- substituted 4-amino-2,4-dihydro-[1 ,2,4]triazole-3-thiones of the formula (I)
(I)
Figure imgf000003_0002
with inorganic or organic nitrites in the presence of a reducing agent in suitable organic solvents.
In conventional diazotation/reduction sequences sometimes strong acidic conditions do not allow for the presence of sensitive functional groups in other parts of the molecule. Under such conditions it is therefore often found in reactions with compounds according to the present invention, that besides the desired compounds of the formula (III) other products are formed such as desulfurized triazoles of the formula (VI) and dimeric compounds of the formula (VII), that contain a disulfide group.
Figure imgf000004_0001
(VI) (VII)
When using alkyl nitrites in excess preferably the disulfide (VII) is formed and can thus be produced in a directed synthesis. This approach provides several advantages, as the disulfides of the formula (VI I) are obtained in yields that are greater than 80% without residual starting material and with very limited amounts of desulfurized compounds of the formula (VI).
The disulfides of formula (VII) can be reduced to provide corresponding compounds of the formula (II I) in a subsequent reduction step using methods that are well known to the skilled person. Disulfides of the formula (VII) are known to possess microbicidal activity and a process for their preparation by way of oxidation of 2,4-dihydro-[1 ,2,4]triazole-3-thiones has been described in WO 97/43269 (A1 ). However, this process, as it starts from thiono- triazoles, suffers from the disadvantages associated with the preparation of the starting material, as pointed out above. Because certain disulfide compounds of the formula (VII) have fungicidal activity, they are relevant with regards to their use for pathogen control in the agrochemical industry. For that reason there is an ongoing need for improved processes that make disulfides of the formula (VII) available on an industrial scale. Therefore one aspect of the present invention is a process for the preparation of 2- substituted 2,4-dihydro-[1 ,2,4]triazole-3-thiones of the formula (III) wherein is a group (1 )
Figure imgf000005_0001
wherein # shall mean the point of attachment to the triazolo group, and A and B are defined as follows:
A or B is a three-, four-, five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated heterocycle or five-, six-, seven-, eight-, nine- or ten- membered aromatic heterocycle, where the heterocycle contains in each case one, two, three or four heteroatoms from the group consisting of O, N and S; is naphthyl or phenyl; and the respective other variable B or A has one of the meanings mentioned above for A or B or is Ci-Cs-alkyl, Ci-Cs-haloalkyl, C2-C8-alkenyl, C2-C8- haloalkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, or benzodioxolyl; where A and/or B independently of one another are unsubstituted or substituted by one, two, three or four independently selected substituents L; wherein
L is halogen, cyano, nitro, cyanato (OCN), Ci-Cs-alkyl, Ci-Cs-haloalkyl, phenyl-Ci-C6-alkyloxy, C2-Cs-alkenyl, C2-C8-haloalkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, C4-Cio-alkadienyl, C4-Cio-haloalkadienyl, Ci-Cs-alk- oxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylcarbonyloxy, Ci-Cs-alkylsulfonyloxy, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8-alkynyloxy, C2-C8- haloalkynyloxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8- cycloalkenyl, Cs-Cs-halocycloalkenyl, Cs-Cs-cycloalkoxy, C3-C6-cyclo- alkenyloxy, hydroxyimino-Ci-Cs-alkyl, Ci-C6-alkylene, oxy-C2-C4- alkylene, oxy-Ci-C3-alkyleneoxy, Ci-Cs-alkoximino-Ci-Cs-alkyl, C2-C8- alkenyloximino-Ci-Cs-alkyl, C2-C8-alkynyloximino-Ci-C8-alkyl, S(=0)nA1, C(=0)A2, C(=S)A2, NA3A4, phenyl-Ci-C8-alkyl, phenyl, phenyloxy or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S; where n, A1, A2, A5, A6 are: n is 0, 1 or 2; is hydrogen, hydroxyl, Ci-Cs-alkyl, Ci-Cs-haloalkyl, amino, Ci-Cs alkylamino or di-Ci-Cs-alkylamino, is one of the groups mentioned for A1 or C2-Cs-alkenyl, C2-C8 haloalkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, Ci-Cs-alkoxy, Ci-Cs haloalkoxy, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8 alkynyloxy, C2-C8-haloalkynyloxy, Cs-Cs-cycloalkyl, C3-C8 halocycloalkyl, C3-Cs-cycloalkoxy or Cs-Cs-halocycloalkoxy;
A5, A6 independently of one another are hydrogen, Ci-Cs-alkyl,
Ci-Cs-haloalkyl, C2-Cs-alkenyl , C2-C8-haloalkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-C8- cycloalkenyl or C3-Cs-halocycloalkenyl; where the aliphatic and/or alicyclic and/or aromatic groups of the radical definitions of L for their part may carry one, two, three or four identical or different groups RL: is halogen, cyano, nitro, Ci-Cs-alkyl, Ci-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Cs-Cs-cycloalkyl , C3-Cs-halocycloal kyl , C3-C8- cycloalkenyl, C3-Cs-cycloalkoxy, Cs-Cs-halocycloalkoxy, Ci-Cs- alkylcarbonyl, Ci-Cs-alkylcarbonyloxy, Ci-Cs-alkoxycarbonyl, amino, Ci-Cs-alkylamino, di-Ci-Cs-alkylamino; or is a group (2)
Figure imgf000006_0001
wherein
# shall mean the point of attachment to the triazolo group and R11 and R22 have the following meanings:
R11, R22 independently of one another Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl or phenyl, wherein the alkyl, cycloalkyl and phenyl moieties may be unsubstituted or substituted by one, two, three or four substituents L; or
R11 and R22, together with the carbon atom to which they are attached, form a five- or six-membered saturated or partially unsaturated ring, that can be unsubstituted or substituted by one, two, three, four or five substituents L', wherein L' stands for L as defined above or stands for a group
Figure imgf000007_0001
wherein R33 and R44 independently are selected from the group of hydrogen and the meaning for L as defined above. is a group (3)
Figure imgf000007_0002
wherein
# shall mean the point of attachment to the triazolo group and R55, R66 and R; have the following meanings:
?55 phenyl-Ci-Cs-alkyI, phenyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S; where the aliphatic and/or aromatic and/or heterocyclic groups for their part may carry one, two, three or four identical or different groups selected from halogen, cyano, nitro, Ci-Cs-alkyl, Ci-Cs-haloalkyl, d-Cs-alkoxy, Ci-Cs- haloalkoxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkenyl, C3-C8-cycloalkoxy, Cs-Cs-halocycloalkoxy, d-Cs-alkylcarbonyl, d-Cs- alkylcarbonyloxy, d-Cs-alkoxycarbonyl, amino, d-Cs-alkylamino, di-d- Cs-alkylamino, phenyl, halophenyl, phenyloxy, halophenyloxy; independently of one another are hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl or phenyl, wherein the alkyl, cycloalkyl or phenyl moieties may be unsubstituted or substituted by one, two or three substituents selected from halogen, cyano, nitro, d-Cs- alkyl, d-Cs-haloalkyl, d-Cs-alkoxy, d-Cs-haloalkoxy; comprising the steps i) diazotation of 2-substituted 4-amino-2,4-dihydro-[1 ,2,4]triazole-3-thiones of formula (I)
wherein
Figure imgf000007_0003
R is defined as above by treatment with inorganic nitrites and an acid or in the presence of organic nitrites in an organic solvent or water or mixtures thereof giving the corresponding compound of formula (VIII).
Figure imgf000008_0001
wherein
R is defined as above and is an anion selected from fluoride, chloride, bromide, iodide, arylsulfonate, alkylsulfonate, haloalkylsulfonate or X01OSO3, in which X01 is CrC8-alkyl, Ci-C8-haloalkyl or C3-C8-cycloalkyl where above mentioned alkyl, haloalkyl or aryl groups are unsubstituted or substituted by one, two, three or four independently selected inert substituents sulfate, sulfonate, phosphate, phosponate, tetrafluoroborate, tetraphenylborate, hexafluorophosphate, hexafluoroarsenate, hexafluoroantimonate, trifluoroacetate, trichloroace- tate, perchlorate, Ci-Cio-alkoxide, hydroxide ii) reduction of a compound of the formula (VIII) to provide mixtures of compounds of the formula (III) and c II),
Figure imgf000008_0002
(VII)
wherein
R is defined as above, by means of a reducing agent; iii) treating the reaction mixture with a reducing reagent suitable to cleave disulfide groups. In view of a concise and efficient preparation of compounds of the formula (III) the present invention also relates to a process for the deamination of compounds of the formula (I) by way of conducting step i), step ii) and step iii) in one vessel (one-pot procedure) with successive addition of reagents or solvents.
The diazotation of an aromatic amine and replacement of the diazo group by hydrogen is well known to the skilled person and can be achieved as previously described in prior art (Organic Reactions 1944, 2, 262; Organic Reactions 1953, 7, 263; Comprehensive Organic Synthesis 1991 , 8, 81 1 ). One suitable way is to treat compounds of the for- mula (I) with inorganic nitrites or organic nitrites. Suitable inorganic nitrites can be, for example, alkali metal nitrites or alkaline earth metal nitrites. According to one embodiment of the present invention preferably sodium nitrite and potassium nitrite are used. According to another embodiment of the present invention Ci-Cio-alkylnitrites, for example n-butyl nitrite, iso-butyl nitrite, tert-butyl nitrite and isoamyl nitrite are preferred.
The diazotation step i) with inorganic nitrites requires the addition of an acid, preferably a strong acid such as hydrochloric acid, sulfuric acid, phosphoric acid or hypophos- phoric acid. The reaction is carried out at temperatures from -10 to 60 °C, according to a preferred embodiment of the invention the reaction is carried out at temperatures from 0 to 30 °C.
The diazotation step i) with organic nitrites is preferably carried out at temperatures from 0 to 60°C, according to a preferred embodiment of the invention the reaction is carried out at temperatures from 10 to 40°C.
Suitable reducing agents in step ii) are, for example, Ci-Cio-alkanols such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, 2-butanol, iso-butanol, pentanol, 2-ethyl- hexanol or formic acid and its salts such as ammonium formate, esters of C1-C4- alkanoles with formic acid, formic amides such as formamide or mercaptanes or alka- line metal borohydrides or tin(ll) salts, phosphonic acid, hypophosponic acid can be used. According to the invention the use of Ci-Cio-alkanols is preferred, particularly n- butanol and iso-butanol are preferred.
The reaction components in carrying out the diazotation of compounds of the formula (I) are usually employed in amounts such that 1 to 10 moles, in particular 1 to 3, more particularly 1 to 2 moles of inorganic nitrite are used per mole of the compound (I) while at least the same amount of reducing agent is added with the inorganic nitrite. It may be preferred if 1 to 1 .5 moles of inorganic nitrite are used per mole of the compound (I) while the same amount of reducing agent is added with the inorganic nitrite.
Another preferred embodiment of the present invention is that 1 to 5 moles of alkyl nitrite are used per mole of the compound (I). Still another preferred embodiment of the present invention is if 1 to 2 moles of alkyl nitrite are used per mole of the compound (I)-
Another embodiment of the present invention is that, when using an inorganic nitrite for the diazotation, 0.1 to 1 moles of a strong acid are used per mole of the compound (I). Still another preferred embodiment of the present invention is if 0.5 to 1 moles of a strong acid are used per mole of the compound (I).
Solvents that can be employed in such diazotation/reduction sequences provide ap- propriate solubility of the starting materials, i.e. compounds of the formula (I), and are also suitable to at least partially dissolve the nitrite and/or the reducing agent. According to the present invention preferably water or aqueous mixtures of water soluble solvents can be used. Examples for such solvents are Ci-C6-alkanols such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, 2-butanol, iso-butanol, tert-butanol, n- pentanol and 2-ethylhexanol or dimethyl sulfoxide, Ν,Ν-dimethylformamide, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone or cyclic ethers such as dioxane and tetrahydrofuran, 2-methyltetrahydrofuran, or nitriles such as acetonitrile and propionitrile or ketones, for example di-Ci-C6-alkyl ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone are used. Solvents such as water, Ci-C6-alkanols, tetrahydrofuran, dioxane and N-methylpyrrolidon are particularly preferred.
According to one preferred embodiment the present invention relates to solvents in the diazotation/reduction sequences that are water or protic solvents or mixtures of water and protic solvents.
According to another preferred embodiment the present invention relates to solvents in the diazotation/reduction sequences that are water, n-butanol, iso-butanol, tert-butanol, tetrahydrofuran and toluene.
According to another preferred embodiment the present invention relates to solvents in the diazotation/reduction sequences that are water, n-butanol, iso-butanol or tert- butanol,. According to another preferred embodiment the present invention relates to tetrahydrofuran as solvent in the diazotation/reduction sequences.
According to another preferred embodiment the present invention relates to solvents in the diazotation/reduction sequences that are water or toluene.
According to another preferred embodiment the present invention relates to solvents in the diazotation/reduction sequences that are iso-butanol or n-butanol. According to one embodiment the present invention suitable counterions Y_ of said dia- zonium compounds of the formula (VIII) are halides, for example chloride, bromide, iodide or arylsulfonates, for example benzenesulfonate, p-tolylsulfonate, 2- nitrophenylsulfonate, 4-nitrophenylsulfonate, 4-bromophenylsulfonate or alkylsul- fonates, for example methanesulfonate or haloalkylsulfonates, for example trifluoro- methylsulfonate, nonafluorobutylsulfonate or alkyl- and haloalkylsulfates, for example methylsulfate where above mentioned alkyl, haloalkyl or aryl groups are unsubstituted or substituted by one, two, three or four independently selected inert substituents, sul- fate, sulfonate, phosphate, phosponate, tetrafluoroborate, tetraphenylborate, hex- afluorophosphate, hexafluoroarsenate, hexafluoroantimonate, trifluoroacetate, tri- chloroacetate, perchlorate, Ci-Cio-alkoxide, hydroxide.
According to a preferred embodiment the present invention the counterion Y- is an an- ion selected from fluoride, chloride, bromide, sulfate, sulfonate, phosphate, phosponate, tetrafluoroborate, tetraphenylborate, hexafluorophosphate, hexafluoroarsenate, hexafluoroantimonate.
According to another preferred embodiment the present invention the counterion Y- is an anion selected from Ci-Cio-alkoxide or hydroxide.
Typically according to the invention the duration of diazotation reactions as described in step i) of the process is between 5 and 60 minutes and is accompanied by the formation of IS O-gas.
The reductive cleavage of disulfide compounds of the formula (VII) to provide compounds of the formula (III) according to step iii) can be achieved as previously described in the literature (J. L. Wardell, S. Patai The Chemistry of the Thiol Group 1974, Wiley, New York). The use of sodium dithionite for the cleavage of disulfides has been described in Journal of Organic Chemistry 1945, 10, 381 -335. According to the present invention the reducing agent of step (iii) is preferably selected from the group comprising alkali metal or alkaline earth metal dithionite, alkali metal formate, sulfur dioxide, hydrazine, zinc/ammonium chloride, alkali metal alanate, tin(ll) salts or mixtures thereof. The use of sodium dithionite is particularly preferred.
2-substituted 2,4-dihydro-[1 ,2,4]triazole-3-thiones of the formula (III) usually precipitate from concentrated solutions and the product can be separated from the reaction mixture by filtration. Purification of thus obtained material can be achieved by washing of the precipitate and/or recrystallization.
The novel compounds according to the invention contain chiral centers and are generally obtained in the form of racemates or as diastereomeric mixtures of erythro and threo forms. The erythro and threo diastereomers of the compounds according to the invention can be separated and isolated in pure form, for example, on the basis of their different solubilities or by column chromatography. Using known methods, such uniform pairs of diastereomers can be used to obtain uniform enantiomers.
Accordingly, the invention provides both the pure enantiomers or diastereomers and mixtures thereof. This applies to the compounds according to the invention. The scope of the present invention includes in particular the (R) and (S) isomers and the racemates of the compounds according to the invention, which have centers of chirality. Suitable compounds according to the invention also include all possible stereoisomers (cis/trans isomers) and mixtures thereof.
The compounds according to the invention may be present in various crystal modifications. They are likewise provided by the present invention.
Furthermore, in the inventive process, the reactants used, contain chiral centers and are generally used in the form of racemates or as diastereomeric mixtures of erythro and threo forms. The erythro and threo diastereomers of these compounds can be separated and isolated in pure form, for example, on the basis of their different solubilities or by column chromatography. Using known methods, such uniform pairs of diastereomers can be used to obtain uniform enantiomers.
Accordingly, the invention provides both the use of pure enantiomers or diastereomers and mixtures thereof. The scope of the present invention includes in particular the use of the (R) and (S) isomers and the racemates of the rspective reactants, which have centers of chirality. Suitable compounds used according to the invention also include all possible stereoisomers (cis/trans isomers) and mixtures thereof.
The compounds used according to the invention may be present in various crystal modifications. They are likewise possible to be used in the inventive process.
4-Amino-2,4-dihydro-[1 ,2,4]triazole-3-thione compounds of the formula (I) can be prepared as described in an application that was filed on the same day as the present application. In view of a concise and efficient preparation of compounds of the formula (III) the present invention also relates to a process for the preparation of compounds of the formula (III) by way of an alkylation/thiolation sequentce to provide compounds of the formula (I) as set forth in the application mentioned above, followed by the diazotation/reduction sequence as described above, comprising step i), step ii) and step iii). All steps are conducted in one vessel (one-pot procedure) with successive addition of reagents or solvents. In some of the definitions of the symbols in the formulae given herein, collective terms are used which are generally representative of the following substituents: halogen: fluorine, chlorine, bromine and iodine; alkyl and the alkyl moieties of composite groups such as, for example, alkylamino: saturated straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 12 carbon atoms, for example Ci-C6-alkyl, such as methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-me- thylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,
1 .1 - dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dime- thylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-tri- methylpropyl, 1 -ethyl-1 -methylpropyl and 1 -ethyl-2-methyl propyl;
haloalkyi: alkyl as mentioned above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above; in particular C1-C2- haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2- dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1 ,1 ,1 -trifluoroprop-2-yl alkenyl and also the alkenyl moieties in composite groups, such as alkenyloxy:
unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one double bond in any position. According to the invention, it may be preferred to use small alkenyl groups, such as (C2-C4)-alkenyl; on the other hand, it may also be preferred to employ larger alkenyl groups, such as (C5-C8)-alkenyl. Examples of alkenyl groups are, for example, C2-C6-alkenyl, such as ethenyl, 1 - propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 - propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-1 - butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 -methyl-3- butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1 -dimethyl-2-propenyl, 1 ,2-dimethyl-
1 - propenyl, 1 ,2-dimethyl-2-propenyl, 1 -ethyl-1 -propenyl, 1 -ethyl-2-propenyl, 1 -hexenyl,
2- hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl-1 -pentenyl, 2-methyl-1 -pentenyl, 3-methyl-1 -pentenyl, 4-methyl-1 -pentenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3- methyl-2-pentenyl, 4-methyl-2-pentenyl, 1 -methyl-3-pentenyl, 2-methyl-3-pentenyl, 3- methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl-4-pentenyl, 2-methyl-4-pentenyl, 3- methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1 -dimethyl-2-butenyl, 1 ,1 -dimethyl-3-butenyl,
1 .2- dimethyl-1 -butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1 - butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3- dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1 - butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl-1 -butenyl, 1 -ethyl-2-butenyl, 1 -ethyl-3-butenyl, 2- ethyl-1 -butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1 - ethyl-1 -methyl-2-propenyl, 1 -ethyl-2-methyl-1 -propenyl and 1 -ethyl-2-methyl-2- propenyl; haloalkenyl: alkenyl as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine; alkadienyl: unsaturated straight-chain or branched hydrocarbon radicals having 4 to 6 or 4 to 8 carbon atoms and two double bonds in any position; alkynyl and the alkynyl moieties in composite groups: straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, for example C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2- propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl,
3- pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3- methyl-1 -butynyl, 1 ,1 -dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3- hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1 -methyl-3-pentynyl, 1 -methyl-4- pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1 -pentynyl, 3-methyl-4- pentynyl, 4-methyl-1 -pentynyl, 4-methyl-2-pentynyl, 1 ,1 -dimethyl-2-butynyl, 1 ,1 - dimethyl-3-butynyl, 1 ,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1 - butynyl, 1 -ethyl-2-butynyl, 1 -ethyl-3-butynyl, 2-ethyl-3-butynyl and 1 -ethyl-1 -methyl-2- propynyl; haloalkynyl: alkynyl as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine; cycloalkyi and also the cycloalkyi moieties in composite groups: mono- or bicyclic saturated hydrocarbon groups having 3 to 8, in particular 3 to 6, carbon ring members, for example C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; halocycloalkyi: cycloalkyi as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine; cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having preferably 3 to 8 or 4 to 6, in particular 5 to 6, carbon ring members, such as cyclopenten-1 -yl, cyclopenten-3-yl, cyclohexen-1 -yl, cyclohexen-3-yl, cyclohexen-4-yl and the like;
halocycloalkenyl: cycloalkenyl as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine; alkoxy: an alkyl group as defined above which is attached via an oxygen, preferably having 1 to 8, more preferably 2 to 6, carbon atoms. Examples are: methoxy, ethoxy, n- propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy or 1 ,1 - dimethylethoxy, and also for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 - ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4- methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl-1 -methylpropoxy or 1 -ethyl-2- methylpropoxy; haloalkoxy: alkoxy as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine. Examples are OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoro- methoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2- difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2- fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2- chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3- bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH2F)-2-fluoroethoxy, 1 -(CH2CI)-2-chloroethoxy, 1 -(CH2Br)-2-bromoethoxy, 4- fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy; and also 5- fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy. alkylene: divalent unbranched chains of CH2 groups. Preference is given to (C1-C6)- alkylene, more preference to (C2-C4)-alkylene; furthermore, it may be preferred to use (Ci-C3)-alkylene groups. Examples of preferred alkylene radicals are CH2, CH2CH2, CH2CH2CH2, CH2(CH2)2CH2, CH2(CH2)3CH2 and CH2(CH2)4CH2; a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle which contains 1 , 2, 3 or 4 heteroatoms from the group consisting of O, N and S, where the heterocycle in question may be attached via a carbon atom or, if present, via a nitrogen atom. According to the invention, it may be preferred for the heterocycle in question to be attached via carbon, on the other hand, it may also be preferred for the heterocycle to be attached via nitrogen. In particular: a three- or four-membered saturated heterocycle (hereinbelow also referred to as heterocyclyl) which contains one or two heteroatoms from the group consisting of O, N and S as ring members; a five- or six-membered saturated or partially unsaturated heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S as ring members: for example monocyclic saturated or partially
unsaturated heterocycles which, in addition to carbon ring members, contain one, two or three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3- isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4- isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5- thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4- oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl,
1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl,
1 ,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-
2- yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3- pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4- yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4- isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2- isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3- isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2- yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4- dihydropyrazol-1 -yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4- dihydropyrazol-5-yl, 4,5-dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5- dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3- dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4- dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydro- oxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1 ,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexa- hydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydro- pyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4-hexahydrotriazin-
3- yl and also the corresponding -ylidene radicals; a seven-membered saturated or partially unsaturated heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S as ring members: for example mono- and bicyclic heterocycles having 7 ring members which, in addition to carbon ring members, contain one, two or three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example tetra- and hexahydroazepinyl, such as 2,3,4,5- tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6-tetrahydro[2H]azepin-2- ,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1 -,-2-,- 3- or-4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2-,- 3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7- tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1 -,-2-,-3- or-4-yl, tetra- and hexahydro-1 ,3-diazepinyl, tetra- and hexahydro-1 ,4-diazepinyl, tetra- and hexahydro-1 ,3-oxazepinyl, tetra- and hexahydro-1 ,4-oxazepinyl, tetra- and hexahydro-1 ,3-dioxepinyl, tetra- and hexahydro-1 ,4-dioxepinyl and the
corresponding ylidene radicals; a 5-, 6-, 7-, 8-, 9- or 10-membered aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms from the group consisting of O, N and S: in particular a five- or six- membered aromatic mono- or bicyclic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S: the heterocycle in question may be attached via a carbon atom or, if present, via a nitrogen atom. According to the invention, it may be preferred for the heterocycle in question to be attached via carbon, on the other hand, it may also be preferred for the heterocycle to be attached via nitrogen. The heterocycle is in particular: a 5-membered heteroaryl which contains one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and/or one sulfur or oxygen atom, where the heteroaryl may be attached via carbon or nitrogen, if present: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one, two or three nitrogen atoms and/or one sulfur or oxygen atom as ring members, for example furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1 ,2,3-; 1 ,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1 ,3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, in particular 2-furyl, 3-furyl, 2-thienyl, 3- thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3- isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2- oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl, 1 ,2,4-thiadiazol-3-yl,
1 ,2,4-thiadiazol-5-yl, 1 ,2,4-triazol-3-yl, 1 ,3,4-oxadiazol-2-yl, 1 ,3,4-thiadiazol-2-yl and 1 ,3,4-triazol-2-yl; a 6-membered heteroaryl which contains one, two, three or four, preferably one, two or three, nitrogen atoms, where the heteroaryl may be attached via carbon or nitrogen, if present: 6-ring heteroaryl groups which, in addition to carbon atoms, may contain one to four or one, two or three nitrogen atoms as ring members, for example pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1 ,2,3-triazinyl, 1 ,2,4-triazinyl, 1 ,3,5-triazinyl, in particular 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1 ,3,5-triazin-2- yl and 1 ,2,4-triazin-3-yl. optionally substituted heterocycle: a saturated heterocycle which is bonded via a ring nitrogen atom and has 5, 6, 7 or 8 ring atoms, where, as well as the nitrogen atom, the ring atoms also further which is unsubstituted or bears 1 , 2, 3, 4 or 5 and especially 1 , 2 or 3 substituents which are inert under the conditions of the reaction. Examples of inert substituents are CN, Ci-C6-alkyl, Ci-C6-alkylthio, Ci-C6-alkylsulfonyl, C1-C4- haloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, and Ci-C4-alkoxy-Ci-C6-alkyl. The heterocycle may, as well as the nitrogen atom in position 1 and the ring carbon atoms, also comprise 1 or 2 further heteroatoms selected from N, O and S as ring atoms. Examples of N-bonded, 5- to 8-membered, saturated, optionally substituted heterocycles are pyr- rolidin-1 -yl, piperdin-1 -yl, morpholin-4-yl, piperazin-1 -yl and N-methylpiperazin-1 -yl; alkylthio: alkyl as defined above which is attached via an S atom; amino: NR1NR2N group, in which R1N and R2N can be alkyl, aryl or heteroaryl as defined above, which is attached via an N atom alkylamino: alkyl as defined above which is attached via N atom; haloalkylthio: haloalkyl as defined above which is attached via an S atom; hydroxy: OH group which is attached via an O atom; carbonitrile: CN group which is attached via an C atom; aldehyde: CHO group, which is attached via an C atom; carboxylic ester: COOR10 group, in which R1° can be alkyl, aryl or heteroaryl as defined above, which is attached via an C atom; mercapto: SH group which is attached via an S atom.
In the following, the meaning of the substituents of the compounds used according to the invention is further defined. Thereby, in each case the substituents are meant to have the given meanings and preferred meaning on their own or in any combination with the meanings or preferred meanings of any other substituent.
According to the present invention R can be in principle any group (1 ), (2) or (3) as defined above that allows carrying out the reaction steps according to the inventive process. If necessary, some reactive groups within the group R can be protected via suitable protecting groups. It is within the skill of a person of the art to choose suitable groups and it is general knowledge of the skilled person how to insert and remove such groups. According to one embodiment of the present invention, the group R in the compounds (III) and precurors thereof carries an epoxide group. In a particular embodiment thereof, R is a group of the formula (1 ) as define above.
In group (1 ) particular preference is given to the following meanings of the substituents, in each case on their own or in combination.
According to one embodiment, A and B independently are unsubstituted phenyl or sub- stituted phenyl containing one, two, three or four independently selected substituents L.
According to one specific embodiment, A is unsubstituted phenyl.
According to a further embodiment, A is phenyl, containing one, two, three or four, in particular one or two, independently selected substituents L, wherein L is as defined or as preferably defined herein. According to one aspect of this embodiment, one of the substituents is in 4-position (para) of the phenyl ring. According to a further aspect, L is in each case independently selected from F, CI, Br, nitro, phenyl, phenoxy, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoro- methyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and trifluorochloro- methyl. According to another specific aspect, L is in each case independently selected from F, CI and Br, in particular F and CI.
According to another embodiment, A is monosubstituted phenyl, containing one sub- stituent L, wherein L is as defined or as preferably defined herein. According to one aspect, said substituent is in para-position.
According to a specific embodiment, A is 3-fluorophenyl. According to another embodiment, A is phenyl, containing two or three independently selected substituents L.
According to another preferred embodiment of the invention, A is phenyl which is substituted by one F and contains a further substituent L, where the phenyl may additionally contain one or two substituents L selected independently of one another, wherein L is as defined or preferably defined herein. According to a preferred embodiment, A is a group A-1
Figure imgf000019_0001
in which # is the point of attachment of the phenyl ring to the oxirane ring; and
L2 is selected from the group consisting of F, CI , NO2, phenyl, halogenphenyl, phenoxy, halogenphenoxy, Ci-C4-al kyl , Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy and Ci-C4-haloalkylthio;
L3 is independently selected from the group consisting of F, CI, Br, NO2, phenyl, halogenphenyl, phenoxy, halogenphenoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio; and
m is 0, 1 or 2. In one embodiment, L2 is selected from the group consisting of F, CI, methyl, methoxy, CF3, CHF2, OCF3, OCF3 and OCHF2. According to a more specific embodiment, L2 is F or CI.
In one embodiment, L3 is independently selected from the group consisting of F, CI, methyl, methoxy, CF3, CH F2, OCF3, OCF3 or OCHF2. According to a more specific embodiment, L3 is independently F or CI.
According to a preferred embodiment, m = 0. According to a further preferred embodiment, m = 1.
In the formula A-1 , the fluorine substituent is, according to a preferred embodiment, in the 4-position.
According to still another embodiment, A is disubstituted phenyl, containing exactly two substituents L that are independently selected from each other, wherein L is as defined or as preferably defined herein. In particular, L is in each case independently selected from F, CI, Br, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, in particular selected from F, CI, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, in particular selected from F, CI, methyl, trifluoromethyl and methoxy. According to a further aspect of this embodiment, the second substituent L is selected from methyl, methoxy and chloro. According to another aspect, one of the substituents is in the 4-position of the phenyl ring. According to another specific aspect, A is phenyl containing one F and exactly one further substituent L as defined or preferably defined herein. According to yet a further preferred embodiment, A is disubstituted phenyl which contains one F and a further substituent L selected from the group consisting of CI, C1-C4- alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, in particular selected from the group consisting of CI, methyl, trifluoromethyl and methoxy. The second substituent L is specifically selected from the group consisting of methyl, methoxy and chlorine. According to one aspect thereof, one of the substituents is located in the 4-position of the phenyl ring. According to another specific embodiment, A is 2,4-disubstituted phenyl. According to still another specific embodiment, A is 2,3-disubstituted phenyl. According to still another specific embodiment, A is 2,5-disubstituted phenyl. According to still another specific embodiment, A is 2,6-disubstituted phenyl. According to still another specific em- bodiment, A is 3,4-disubstituted phenyl. According to still another specific embodiment, A is 3,5-disubstituted phenyl.
According to a further preferred embodiment of the invention, A is phenyl which is substituted by exactly two F. According to one aspect, A is 2,3-difluoro-substituted. According to a further aspect, A is 2,4-difluoro-substituted. According to yet a further aspect, A is 2,5-difluoro-substituted. According to yet a further aspect, A is 2,6-difluoro- substituted. According to yet a further aspect, A is 3,4-difluoro-substituted. According to yet a further aspect, A is 3,5-difluoro-substituted. According to a further embodiment, A is trisubstituted phenyl containing exactly three independently selected substituents L, wherein L is as defined or preferably defined herein. According to yet a further embodiment, A is phenyl which is substituted by exactly three F. According to one aspect, A is 2,3,4-trisubstituted, in particular 2,3,4- trifluoro-substituted. According to another aspect, A is 2,3,5-trisubstituted, in particular 2,3,5-trifluoro-substituted. According to still another aspect, A is 2,3,6-trisubstituted, in particular 2,3, 6-trifluoro-substituted. According to still another aspect, A is 2 ,4,6- trisubstituted, in particular 2,4, 6-trifluoro-substituted. According to still another aspect, A is 3,4,5-trisubstituted, in particular 3,4,5-trifluoro-substituted. According to still another aspect, A is 2,4,5-trisubstituted, in particular 2, 4, 5-trifluoro-substituted.
According to a preferred embodiment, B is phenyl, that is unsubstituted or phenyl which contains one, two, three or four independently selected substituents L, wherein L is as defined or preferably defined herein. According to one embodiment of the invention, B is unsubstituted phenyl.
According to a further embodiment, B is phenyl which contains one, two, three or four independently selected substituents L, wherein L is as defined or preferably defined herein.
According to a further embodiment, B is phenyl which contains one, two or three, preferably one or two, independently selected substituents L, wherein L is as defined or preferably defined herein. Accord i ng to a specific aspect, L is i n each case independently selected from F, CI, Br, methyl, methoxy and trifluoromethyl. According to still another embodiment, B is phenyl, which contains one, two or three, preferably, one or two, halogen substituents. According to a further embodiment, B is phenyl which contains one, two, three or four substituents L, wherein L is independently selected from F, CI, Br, methyl, ethyl, iso- propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, di- fluorochloromethyl, trifluoromethoxy, difluoromethoxy and difluorochloromethyl. Accord- ing to a specific aspect, L is in each case independently selected from F, CI and Br.
According to still a further embodiment, B is unsubstituted phenyl or phenyl which contains one, two or three substituents independently selected from halogen, NO2, amino, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylamino, Ci-C4-dialkylamino, thio and Ci-C4-alkylthio.
According to a further embodiment, B is a phenyl ring that is monosubstituted by one substituent L, where according to a special aspect of this embodiment, L is located in the ortho-position to the point of attachment of the phenyl ring to the oxirane ring. L is as defined or preferably defined herein. According to a further specific embodiment, B is monochloro-substituted phenyl, in particular 2- chlorophenyl.
According to a further embodiment, B is phenyl, which contains two or three, in particular two, independently selected substituents L, wherein L is as defined or preferably defined herein.
According to a further embodiment of the invention, B is a phenyl ring which contains a substituent L in the ortho-position and furthermore has one further independently selected substituent L. According to one aspect, the phenyl ring is 2,3-disubstituted. According to a further aspect, the phenyl ring is 2,4-disubstituted. According to yet a further aspect, the phenyl ring is 2,5-disubstituted. According to yet a further aspect, the phenyl ring is 2,6-disubstituted.
According to a further embodiment of the invention, B is a phenyl ring which contains a substituent L in the ortho-position and furthermore contains two further independently selected substituents L. According to one aspect, the phenyl ring is 2,3,5-trisubstituted. According to a further aspect, the phenyl ring is 2,3,4-trisubstituted. According to yet a further aspect, the phenyl ring is 2,4,5-trisubstituted. In a further embodiment, B is phenyl which contains one substituent L in the 2-position and one, two or three further independently selected substituents L. According to a preferred embodiment, B is a group B-1
# in which # denotes the point of attachment of the phenyl ring to the oxirane ring; and L1 is selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio, preferably selected from the group consisting of F, CI, methyl, ethyl, methoxy, ethoxy, CF3, CH F2, OCF3,
Figure imgf000023_0001
L2 is selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio, preferably selected from the group consisting of F, CI, methyl, ethyl, methoxy, ethoxy, CF3, CH F2, OCF3,
Figure imgf000023_0002
L3 is independently selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-ha l oa l kyl , Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-C4-haloalkylthio, preferably selected from the group consisting of F, CI, methyl, ethyl, methoxy, ethoxy, CF3, CHF2, OCF3, OCHF2 and SCF3; and
m is 0, 1 or 2.
According to a preferred embodiment, L1 is F. According to another preferred embodiment, L1 is CI. According to a further preferred embodiment, L1 is methyl. According to yet a further preferred embodiment, L1 is methoxy. According to yet a further preferred embodiment, L1 is CF3. According to yet a further preferred embodiment, L1 is OCF3 or OCHF2. According to a preferred embodiment, in the compounds of the formula I according to the invention, B is thus phenyl which contains a substituent selected from the group consisting of F, CI, CH3, OCH3, CF3, CHF2, OCF3 and OCHF2 in the 2-position and one or two further independently selected substituents L.
According to a further preferred embodiment, L2 is F. According to another preferred embodiment, L2 is CI . According to a further preferred embodiment, L2 is methyl. According to yet a further preferred embodiment, L2 is methoxy. According to yet a further preferred embodiment, L2 is CF3. Accord i ng to yet a further preferred embodiment, L2 is OCF3 or OCHF2.
According to a preferred embodiment, L3 is F. According to another preferred embodiment, L3 is CI. According to a further preferred embodiment, L3 is methyl. According to yet a further preferred embodiment, L3 is methoxy. According to yet a further preferred embodiment, L3 is CF3. Accord i ng to yet a further preferred embodiment, L3 is OCF3 or OCHF2.
According to a preferred embodiment, m = 0; i.e. B is a disubstituted phenyl ring. According to a preferred aspect, B is a 2,3-disubstituted phenyl ring. According to a further preferred aspect, the pheny ring B is 2,4-disubstituted. According to yet a further preferred aspect, the phenyl ring B is 2,5-disubstituted. According to yet a further preferred aspect, the phenyl ring is 2,6-disubstituted. According to a further preferred embodiment, m = 1 ; i.e. B is a trisubstituted phenyl ring. According to a preferred aspect, the phenyl ring B is 2,3,5-trisubstituted. According to another preferred further aspect, the phenyl ring B is 2,3,4-trisubstituted. According to yet a further preferred embodiment, the phenyl ring B is 2,4,5- trisubstituted.
Unless indicated otherwise, in group (1 ) L independently has the following preferred meanings:
According to one embodiment, L is independently selected from the group consisting of halogen, cyano, nitro, cyanato (OCN), Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci- C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, S-A1, C(=0)A2, C(=S)A2, NA3A; where A1, A2, A5, A6 are as defined below:
A1 is hydrogen, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl;
A2 is one of the groups mentioned under A1 or Ci-C4-alkoxy, Ci-C4- haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkoxy or C3-C6-halocycloalkoxy;
A5,A6 independently of one another are hydrogen, Ci-C4-alkyl, Ci-C4-halo- alkyl; where the aliphatic and/or alicyclic groups of the radical definitions of L for their part may carry one, two, three or four identical or different groups RL:
RL is halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, amino, Ci-Cs- alkylamino, di-Ci-Cs-alkylamino.
Furthermore preferably, L is independently selected from the group consisting of halogen, NO2, amino, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci- C4-alkylamino, di-Ci-C4-alkylamino, thio and Ci-C4-alkylthio. Furthermore preferably, L is independently selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and C1-C4- haloalkylthio, in particular halogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
According to a further preferred embodiment, L is independently selected from the group consisting of F, CI, Br, CH3, C2H5, i-C3H7, t-C4H9, OCH3, OC2H5, CF3, CCI3, CHF2, CCIF2, OCF3, OCHF2 and SCF3, in particular selected from the group consisting of F, CI, CH3, C2H5, OCH3, OC2H5, CF3, CHF2, OCF3, OCH F2 and SCF3. According to one aspect, L is independently selected from the group consisting of F, CI, CH3, OCH3, CF3, OCF3 and OCHF2. It may be preferred for L to be independently F or CI.
According to one preferred embodiment, A and B are as defined as follows:
A phenyl, which is unsubstituted or substituted by one, two or three substituents L that may be the same or different, independently selected from F, CI, Br, nitro, phenyl, phenoxy, methyl, ethyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, di- fluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and trifluoro- methylthio; and
B phenyl, that is substituted by one, two or three substituents L that may be the same or different, independently selected from F, CI, Br, methyl, ethyl, iso-propyl, tert- butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloro- methyl, trifluoromethoxy, difluoromethoxy and trifluoromethylthio.
In specific groups (1 ) A and B are defined as follows:
A i s ph enyl , 4-chlorophenyl, 2,4-chlorophenyl, 2-chlorophenyl, 2-fluorophenyl, 4- fluorophenyl, 4-methylphenyl, 3-bromo-4-fl uorophenyl , 4-bromophenyl, 3,4- d ichlorophenyl , 4-tert-butyl-phenyl, 3-chlorophenyl, 3,5-dichlorophenyl or 4- trifluoromethoxypghenyl and B is 2-chlorophenyl. In one specific group (1 ) A is 4- flourphenyl and B is 2-chlorophenyl. A is 4-fluorophenyl and B is 2-difluoromethoxyphenyl.
A i s ph enyl , 4-chlorophenyl, 2,4-chlorophenyl, 2-chlorophenyl, 2-fluorophenyl, 4- methylphenyl, 4-fluorophenyl, 3-bromo-4-fluorophenyl, 4-bromophenyl, 3,4- dichlorophenyl, 4-tert-butyl-phenyl, 3-chlorophenyl, 3,5-dichlorophenyl or 4- trifluoromethoxyphenyl, and B is 2-fluorophenyl.
A i s phe nyl, 4-chlorophenyl, 2,4-chlorophenyl, 2-chlorophenyl, 2-fluorophenyl, 4- methylphenyl, 4-fluorophenyl, 3-bromo-4-fluorophenyl, 4-bromophenyl, 3,4- dichlorophenyl, 4-tert-butyl-phenyl, 3-chlorophenyl, 3,5-dichlorophenyl or 4- trifluoromethoxyphenyl, and B is 2-bromophenyl.
In further specific groups (1 ) A and B are defined as follows:
A is 2,4-difluorophenyl and B is 2-chlorophenyl.
A is 3,4-difluorophenyl and B is 2-chlorophenyl.
A is 2,4-difluorophenyl and B is 2-fluorophenyl.
A is 3,4-difluorophenyl and B is 2-fluorophenyl. A is 2,4-difluorophenyl and B is 2-trifluoromethylphenyl.
A is 3,4-difluorophenyl and B is 2-trifluoromethylphenyl.
A is 3,4-difluorophenyl and B is 2-methylphenyl In further specific groups (1 ) A and B are defined as follows:
A is phenyl and B is 2,4-dichlorophenyl.
A is phenyl and B is 2-fluoro-3-chlorophenyl.
A is phenyl and B is 2,3,4-trichlorophenyl.
A is 4-fluorophenyl and B is 2,4-dichlorophenyl.
A is 4-fluorophenyl and B is 2-fluoro-3-chlorophenyl.
A is 4-fluorophenyl and B is 2,3,4-trichlorophenyl.
A is 2-chlorophenyl and B is 2,4-dichlorophenyl.
A is 2-chlorophenyl and B is 2-fluoro-3-chlorophenyl.
A is 2-chlorophenyl and B is 2,3,4-trichlorophenyl.
The meanings described above of the variables A, B and L for groups (1 ) apply for R = group (1 ) in compounds (III) and to the precursors/intermediates of the inventive process such as compounds of the formula (I), (VII) and (VIII).
According to the inventive process, the pure enantiomers or a mixture of enantiomers (racemic or enantiomerically enriched) of the reactants, in particular of compounds of the formula (I), can be used. For example, the following different stereoisomers of compounds (l)-(1 ) can be employed in the inventive process: compound (l)-(1 )-a1 ):
Formula (l)-(1 ), wherein A is 4-fluoro-phenyl and B is 2-chlorophenyl
4-amino-2-[(2S,3S)-3-(2-Chloro-phenyl)-2-(4-fluoro-phenyl)-oxiranylmethyl]-2H-
[1 ,2,4]triazole-3-thione ("cis")
compound (l)-(1 )-a2):
Formula (l)-(1 ), wherein A is 4-fluoro-phenyl and B is 2-chlorophenyl
4-amino-2-[(2R,3R)-3-(2-Chloro-phenyl)-2-(4-fluoro-phenyl)-oxiranylmethyl]-2H-
[1 ,2,4]triazole-3-thione ("cis")
compound (l)-(1 )-a3):
Formula (l)-(1 ), wherein A is 4-fluoro-phenyl and B is 2-chlorophenyl
4-amino-2-[(2S,3R)-3-(2-Chloro-phenyl)-2-(4-fluoro-phenyl)-oxiranylmethyl]-2H-
[1 ,2,4]triazole-3-thione ("trans")
compound (l)-(1 )-a4):
Formula (l)-(1 ), wherein A is 4-fluoro-phenyl and B is 2-chlorophenyl
4-amino-2-[(2R,3S)-3-(2-Chloro-phenyl)-2-(4-fluoro-phenyl)-oxiranylmethyl]-2H- [1 ,2,4]triazole-3-thione ("trans")
compound (l)-(1 )-b1 ): Formula (l)-(1 ), wherein A is 2,4-difluoro-phenyl and B is 2-chlorophenyl
4-amino-2-[(2S,3S)-3-(2-Chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]-2H- [1 ,2,4]triazole-3-thione ("cis")
compound (l)-(1 )-b2):
Formula (l)-(1 ), wherein A is 2,4-difluoro-phenyl and B is 2-chlorophenyl
4-amino-2-[(2R,3R)-3-(2-Chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]-2H- [1 ,2,4]triazole-3-thione ("cis")
compound (l)-(1 )-b3):
Formula (l)-(1 ), wherein A is 2,4-difluoro-phenyl and B is 2-chlorophenyl
4-amino-2-[(2S,3R)-3-(2-Chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]-2H- [1 ,2,4]triazole-3-thione ("trans")
compound (l)-(1 )-b4):
Formula (l)-(1 ), wherein A is 2,4-difluoro-phenyl and B is 2-chlorophenyl
4-amino-2-[(2R,3S)-3-(2-Chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]-2H- [1 ,2,4]triazole-3-thione ("trans")
With respect to the fungicidal activity of the end products, it may be preferred, if the "trans" diastereomers are synthesized in the inventive process. According to another embodiment of the present invention, the organic group R in the compounds (III) and precursors thereof carries a free hydroxy group and compounds (III) are from the triazole class of fungicides. In a particular embodiment thereof, R is a group of the formula (2) as defined above. According to one embodiment, R11 and R22 in the group of formula (2) are preferably independently selected from Ci-C4-alkyl and phenyl , wherein the alkyl and phenyl group independently may contain one, two, three or four substituents , independently selected from F, CI, Br, methoxy, ethoxy, propoxy, isopropoxy, Ci-C2-alkoximino, cy- clopropyl, cyclobutyl, cyclopentyl and/or cyclohexyl. Specifically, R11 stands for C1-C4- alkyl that is substituted by one or two substituents independently selected from F, CI, methoxy, cyclopropyl, cyclopentyl and/or cyclohexyl and R22 stands for phenyl, that is substituted by one, two, three or four substituents independently selected from F, CI, Br and methoxy. In one specific embodiment, R11 is 1 -ethyl that is 1 -substituted by cyclopropyl and R22 is 4-chlorophenyl. According to another specific embodiment, R11 is n- butyl and R22 is 2,4-dichlorophenyl.
According to another embodiment, R11 and R22 are preferably independently selected from Ci-C4-alkyl, phenyl-Ci-C4-alkyl and C3-C6-cycloalkyl, preferably phenyl-Ci-C4-alkyl and C3-C6-cycloalkyl, wherein the alkyl, phenyl and cycloalkyl groups independently may contain one, two, three or four substituents , independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl and/or tert-butyl. Specifically, R11 stands for phenyl- Ci-C4-alkyl that is substituted in the phenyl moiety by one, two, three or four substitu- ents independently selected from F, CI and methoxy and R22 stands for C3-C6- cycloalkyl, that is substituted by one, two, three or four substituents independently selected from F , C I , Br a nd methoxy. I n one specifi c em bod i ment, R11 is 2- chlorophenylmethyl and R22 is 1 -chlorocyclopropyl.
According to still another embodiment, R11 and R22 are preferably independently selected from Ci-C4-alkyl and phenyl-Ci-C4-alkyl, wherein the alkyl and phenyl groups may contain one, two, three or four substituents , independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoro- methyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxyvarbonyl, methoxyiminomethyl, 1 - methoximinoethyl and nitro. Specifically, R11 stands for Ci-C4-alkyl that may be substituted by one or two substituents, independently selected from methyl, ethyl, propyl, isopropyl and tert-butyl and R22 stands for phenyl-Ci-C4-alkyl, that is substituted in the phenyl moiety by one, two, three or four substituents independently selected from F, CI, Br, CN, methyl, trifluoromethyl and methoxy. In one specific embodiment R11 is tert- butyl and R22 is 2-(4-chlorophenyl)-1 -ethyl.
According to still another embodiment, R11 and R22 are preferably independently se- lected from phenyl, wherein the phenyl moieties may contain one, two, three or four substituents , independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxyvarbonyl, methoxyiminomethyl, 1-methoximinoethyl and nitro. Specifi- cally, R11 and R22 independently stand for phenyl, that may contain one, two or three substituents , independently selected from F, CI and Br. In one specific embodiment R11 is 2-fluorophenyl and R22 is 4-fluorophenyl.
According to still another embodiment, preferably R11 and R22, together with the carbon atom to which they are attached, form a five- or six-membered saturated ring, that can be unsubstituted or substituted by one, two or three substituents L', wherein L' stands for L as defined above or stands for a group
Figure imgf000028_0001
ently are selected from the group of hydrogen, Ci-C4-alkyl and phenyl, wherein the alkyl and phenyl groups may contain one, two, three or four substituents , independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy and nitro. Specifically, R11 and R22, together with the carbon atom to which they are attached, form a five-membered saturated ring, that is substituted by one, two or three substituents L', wherein L' stands for Ci-C4-alkyl or for a group
Figure imgf000029_0001
wherein R33 and R44 independently are selected from the group of hydrogen, Ci-C4-alkyl and phenyl, wherein the alkyl and phenyl groups may contain one, two, three or four substituents , independently selected from F, CI, CN, methyl, isopro- pyl, tert-butyl and methoxy. In one specific embodiment R11 and R22, together with the carbon atom to which they are attached, form a five-membered saturated substituted in 5-position by two methyl groups and contains a group
Figure imgf000029_0002
wherein R33 is hydrogen and R44 is 4-chlorophenyl in 2-position.
According to still another embodiment, R11 and R22, together with the carbon atom to which they are attached, form a five- or six-membered saturated ring, that can be unsubstituted or substituted by one, two or three substituents, independently selected from F, CI, Br, CN, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, methyl- thio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, di- fluoromethoxy, nitro, benzyl, wherein the phenyl moiety itself may contain on, two, three or four substituents, independently selected from F, CI, CN, methyl, isopropyl, tert-butyl and methoxy. In one specific embodiment R11 and R22, together with the carbon atom to which they are attached, form a five-membered saturated ring, that is substituted in 5-position by two methyl groups and contains a 4-chlorobenzyl group in 2- position. Regarding compounds (l)-(2) and the synthesis of precursors thereof see also WO 96/16048 (A1 ), WO 96/38423 (A1 ), E P 378953 (B1 ), EP 655443 (A2), DE 4030039 (A1 ), DE 3337937 (A), DE 3315681 (A1 ), US 4414210 (A).
According to another embodiment of the present invention, R in the compounds (I II) and precursors thereof is a group of the formula (3) as defined above.
According to one embodiment, R55 in a group of the formula (3) is phenyl that is unsubstituted or substituted by one, two, three or four substituents independently selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenoxy-Ci-C6-alkyl and halophenyloxy, and R66 and R77 are independently selected from hydrogen, methyl, ethyl, n-propyl and n-butyl. Specifically, R55 is phenyl that contains one, two or three substituents independently selected from F, CI and halophenoxy, wherein the phenoxy moiety contains one or two halogen atoms selected from CI and F; and R66 is hydrogen and R77 is Ci-C4-alkyl. In one specific embodiment R55 is 4-(4-chlorophenoxy)-2- chlorophenyl, R66 is hydrogen and R77 is methyl. In another specific embodiment R55 is 2,4-dichlorophenyl, R66 is hydrogen and R77 is n-propyl.
Regarding compounds (l)-(3) and the synthesis of precursors thereof see also WO 96/41804 (A1 ) and Pestic. Sci. 1980, 11, 95 and Research Disclosure 1989, 297,13. Another aspect of the present invention is diazo compounds of the formula (VIII) in which R is a group of the formula (1), (2) or (3) as defined above.
According to one specific embodiment of the present invention, R in compounds (VIII) is a group (1) as defined above, including the specific embodiments thereof. In particular, compounds (Z)-(1),
Figure imgf000030_0001
in which Y is fluoride (Zl)-(1), chloride (Zll)-(1), bromide (Zlll)-(1), sulfate (ZIV)-(1), sulfonate (ZV)-(1), phosphate (ZVI)-(1), phosphonate (ZVII)-(1), tetrafluoroborate (ZVIII)- (1), tetraphenylborate (ZIX)-(1), hexafluorophosphate (ZX)-(1), hexafluoroarsenate (ZXI)-(1), hexafluoroantimonate (ZXII)-(1) according to the invention, wherein A is defined as in tables 1a to 257a in combination with residues B in rows 1 to 514 of table A below, are suitable for the synthesis of the respective fungicides of formula (111) and are obtained by the inventive process. The groups mentioned for a substituent in the tables are furthermore per se, independently of the combination in which they are mentioned, a particularly preferred aspect of the substituent in question. table 1a
Compounds (Z)-(1), wherein A is 2,3-difluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).1 aA-1 to (Zl)-(1 ).1 aA-514;
compounds (Zll)-(1 ).1 aA-1 to (Zll)-(1 ).1 aA-514;
compounds (Zl ll)-(1 ).1 aA-1 to (ZIII)-(1).1aA-514;
compounds (ZIV)-(1).1aA-1 to (ZIV)-(1).1aA-514;
compounds (ZV)-(1).1aA-1 to (ZV)-(1).1aA-514;
compounds (ZVI)-(1).1aA-1 to (ZVI)-(1).1aA-514;
compounds (ZVII)-(1).1aA-1 to (ZVII)-(1).1aA-514;
compounds (ZVIII)-(1 ).1 aA-1 to (ZVIII)-(1).1aA-514;
compounds (ZIX)-(1).1aA-1 to (ZIX)-(1).1aA-514;
compounds (ZX)-(1).1aA-1 to (ZX)-(1).1aA-514;
compounds (ZXI)-(1).1aA-1 to (ZXI)-(1).1aA-514;
compounds (ZXII)-(1 ).1 aA-1 to (ZXII)-(1).1aA-514)
table 2a
Compounds (Z)-(1), wherein A is 2,4-difluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).2aA-1 to (Zl)-(1 ).2aA-514;
compounds (ZII)-(1).2aA-1 to (ZII)-(1).2aA-514;
compounds (ZIII)-(1).2aA-1 to (ZIII)-(1).2aA-514;
compounds (ZIV)-(1).2aA-1 to (ZIV)-(1).2aA-514;
compounds (ZV)-(1 ).2aA-1 to (ZV)-(1 ).2aA-514;
compounds (ZVI)-(1).2aA-1 to (ZVI)-(1).2aA-514;
compounds (ZVII)-(1).2aA-1 to (ZVII)-(1).2aA-514;
compounds (ZVIII)-(1).2aA-1 to (ZVIII)-(1).2aA-514;
compounds (ZIX)-(1).2aA-1 to (ZIX)-(1).2aA-514;
compounds (ZX)-(1 ).2aA-1 to (ZX)-(1 ).2aA-514;
compounds (ZXI)-(1).2aA-1 to (ZXI)-(1).2aA-514;
compounds (ZXII)-(1).2aA-1 to (ZXII)-(1).2aA-514)
table 3a
Compounds (Z)-(1), wherein A is 2,5-difluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).3aA-1 to (Zl)-(1 ).3aA-514;
compounds (ZII)-(1).3aA-1 to (ZII)-(1).3aA-514;
compounds (ZIII)-(1).3aA-1 to (ZIII)-(1).3aA-514;
compounds (ZIV)-(1).3aA-1 to (ZIV)-(1).3aA-514;
compounds (ZV)-(1).3aA-1 to (ZV)-(1).3aA-514;
compounds (ZVI)-(1 ).3aA-1 to (ZVI)-(1 ).3aA-514;
compounds (ZVII)-(1).3aA-1 to (ZVII)-(1).3aA-514;
compounds (ZVIII)-(1).3aA-1 to (ZVIII)-(1).3aA-514;
compounds (ZIX)-(1).3aA-1 to (ZIX)-(1).3aA-514;
compounds (ZX)-(1).3aA-1 to (ZX)-(1).3aA-514;
compounds (ZXI)-(1 ).3aA-1 to (ZXI)-(1 ).3aA-514;
compounds (ZXII)-(1).3aA-1 to (ZXII)-(1).3aA-514)
table 4a
Compounds (Z)-(1), wherein A is 2,6-difluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).4aA-1 to (Zl)-(1 ).4aA-514;
compounds (ZII)-(1).4aA-1 to (ZII)-(1).4aA-514;
compounds (ZIII)-(1).4aA-1 to (ZIII)-(1).4aA-514;
compounds (ZIV)-(1).4aA-1 to (ZIV)-(1).4aA-514;
compounds (ZV)-(1).4aA-1 to (ZV)-(1).4aA-514;
compounds (ZVI)-(1).4aA-1 to (ZVI)-(1).4aA-514;
compounds (ZVII)-(1).4aA-1 to (ZVII)-(1).4aA-514;
compounds (ZVIII)-(1).4aA-1 to (ZVIII)-(1).4aA-514;
compounds (ZIX)-(1).4aA-1 to (ZIX)-(1).4aA-514;
compounds (ZX)-(1).4aA-1 to (ZX)-(1).4aA-514;
compounds (ZXI)-(1).4aA-1 to (ZXI)-(1).4aA-514;
compounds (ZXII)-(1).4aA-1 to (ZXII)-(1).4aA-514)
table 5a
Compounds (Z)-(1), wherein A is 3,4-difluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).5aA-1 to (Zl)-(1 ).5aA-514;
compounds (ZII)-(1).5aA-1 to (ZII)-(1).5aA-514;
compounds (ZIII)-(1).5aA-1 to (ZIII)-(1).5aA-514;
compounds (ZIV)-(1).5aA-1 to (ZIV)-(1).5aA-514;
compounds (ZV)-(1 ).5aA-1 to (ZV)-(1 ).5aA-514;
compounds (ZVI)-(1).5aA-1 to (ZVI)-(1).5aA-514;
compounds (ZVII)-(1).5aA-1 to (ZVII)-(1).5aA-514;
compounds (ZVIII)-(1).5aA-1 to (ZVIII)-(1).5aA-514;
compounds (ZIX)-(1).5aA-1 to (ZIX)-(1).5aA-514;
compounds (ZX)-(1 ).5aA-1 to (ZX)-(1 ).5aA-514;
compounds (ZXI)-(1).5aA-1 to (ZXI)-(1).5aA-514;
compounds (ZXII)-(1).5aA-1 to (ZXII)-(1).5aA-514)
table 6a
Compounds (Z)-(1), wherein A is 3,5-difluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).6aA-1 to (Zl)-(1 ).6aA-514;
compounds (ZII)-(1).6aA-1 to (ZII)-(1).6aA-514;
compounds (ZIII)-(1).6aA-1 to (ZIII)-(1).6aA-514;
compounds (ZIV)-(1).6aA-1 to (ZIV)-(1).6aA-514;
compounds (ZV)-(1).6aA-1 to (ZV)-(1).6aA-514;
compounds (ZVI)-(1 ).6aA-1 to (ZVI)-(1 ).6aA-514;
compounds (ZVII)-(1).6aA-1 to (ZVII)-(1).6aA-514;
compounds (ZVIII)-(1).6aA-1 to (ZVIII)-(1).6aA-514;
compounds (ZIX)-(1).6aA-1 to (ZIX)-(1).6aA-514;
compounds (ZX)-(1).6aA-1 to (ZX)-(1).6aA-514;
compounds (ZXI)-(1 ).6aA-1 to (ZXI)-(1 ).6aA-514;
compounds (ZXII)-(1).6aA-1 to (ZXII)-(1).6aA-514)
table 7a
Compounds (Z)-(1), wherein A is 2-fluoro-3-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).7aA-1 to (ZI)-(1).7aA-514;
compounds (ZII)-(1).7aA-1 to (ZII)-(1).7aA-514;
compounds (ZIII)-(1).7aA-1 to (ZIII)-(1).7aA-514;
compounds (ZIV)-(1).7aA-1 to (ZIV)-(1).7aA-514;
compounds (ZV)-(1).7aA-1 to (ZV)-(1).7aA-514;
compounds (ZVI)-(1).7aA-1 to (ZVI)-(1).7aA-514;
compounds (ZVII)-(1).7aA-1 to (ZVII)-(1).7aA-514;
compounds (ZVIII)-(1).7aA-1 to (ZVIII)-(1).7aA-514;
compounds (ZIX)-(1).7aA-1 to (ZIX)-(1).7aA-514;
compounds (ZX)-(1).7aA-1 to (ZX)-(1).7aA-514;
compounds (ZXI)-(1).7aA-1 to (ZXI)-(1).7aA-514;
compounds (ZXII)-(1).7aA-1 to (ZXII)-(1).7aA-514)
table 8a
Compounds (Z)-(1), wherein A is 2-fluoro-4-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).8aA-1 to (ZI)-(1).8aA-514;
compounds (ZII)-(1).8aA-1 to (ZII)-(1).8aA-514;
compounds (ZIII)-(1).8aA-1 to (ZIII)-(1).8aA-514;
compounds (ZIV)-(1).8aA-1 to (ZIV)-(1).8aA-514;
compounds (ZV)-(1 ).8aA-1 to (ZV)-(1 ).8aA-514;
compounds (ZVI)-(1).8aA-1 to (ZVI)-(1).8aA-514;
compounds (ZVII)-(1).8aA-1 to (ZVII)-(1).8aA-514;
compounds (ZVIII)-(1).8aA-1 to (ZVIII)-(1).8aA-514;
compounds (ZIX)-(1).8aA-1 to (ZIX)-(1).8aA-514;
compounds (ZX)-(1 ).8aA-1 to (ZX)-(1 ).8aA-514;
compounds (ZXI)-(1).8aA-1 to (ZXI)-(1).8aA-514;
compounds (ZXII)-(1).8aA-1 to (ZXII)-(1).8aA-514)
table 9a
Compounds (Z)-(1), wherein A is 2-fluoro-5-chlorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).9aA-1 to (Zl)-(1 ).9aA-514;
compounds (ZII)-(1).9aA-1 to (ZII)-(1).9aA-514;
compounds (ZIII)-(1).9aA-1 to (ZIII)-(1).9aA-514;
compounds (ZIV)-(1).9aA-1 to (ZIV)-(1).9aA-514;
compounds (ZV)-(1).9aA-1 to (ZV)-(1).9aA-514;
compounds (ZVI)-(1 ).9aA-1 to (ZVI)-(1 ).9aA-514;
compounds (ZVII)-(1).9aA-1 to (ZVII)-(1).9aA-514;
compounds (ZVIII)-(1).9aA-1 to (ZVIII)-(1).9aA-514;
compounds (ZIX)-(1).9aA-1 to (ZIX)-(1).9aA-514;
compounds (ZX)-(1).9aA-1 to (ZX)-(1).9aA-514;
compounds (ZXI)-(1 ).9aA-1 to (ZXI)-(1 ).9aA-514;
compounds (ZXII)-(1).9aA-1 to (ZXII)-(1).9aA-514)
table 10a
Compounds (Z)-(1), wherein A is 2-fluoro-6-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).10aA-1 to (ZI)-(1).10aA-514;
compounds (Zll)-(1 ).10aA-1 to (ZII)-(1).10aA-514;
compounds (ZIII)-(1).10aA-1 to (ZIII)-(1).10aA-514;
compounds (ZIV)-(1).10aA-1 to (ZIV)-(1).10aA-514;
compounds (ZV)-(1).10aA-1 to (ZV)-(1).10aA-514;
compounds (ZVI)-(1).10aA-1 to (ZVI)-(1).10aA-514;
compounds (ZVII)-(1).10aA-1 to (ZVII)-(1).10aA-514;
compounds (ZVIII)-(1 ).10aA-1 to (ZVIII)-(1 ).1 OaA-514;
compounds (ZIX)-(1).10aA-1 to (ZIX)-(1).1 OaA-514;
compounds (ZX)-(1).10aA-1 to (ZX)-(1).1 OaA-514;
compounds (ZXI)-(1).10aA-1 to (ZXI)-(1).1 OaA-514;
compounds (ZXII)-(1).10aA-1 to (ZXII)-(1).1 OaA-514)
table 11a
Compounds (Z)-(1), wherein A is 3-fluoro-4-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).11aA-1 to (ZI)-(1).11aA-514;
compounds (ZII)-(1).11aA-1 to (Zll)-(1 ).11 aA-514;
compounds (ZIII)-(1).11aA-1 to (Zlll)-(1).11 aA-514;
compounds (ZIV)-(1).11aA-1 to (ZIV)-(1).11 aA-514;
compounds (ZV)-(1).11aA-1 to (ZV)-(1).11 aA-514;
compounds (ZVI)-(1).11aA-1 to (ZVI)-(1).11 aA-514;
compounds (ZVII)-(1 ).11 aA-1 to (ZVII)-(1).11aA-514;
compounds (ZVIII)-(1).11aA-1 to (ZVIII)-(1).11aA-514;
compounds (ZIX)-(1).11aA-1 to (ZIX)-(1).11 aA-514;
compounds (ZX)-(1).11 aA-1 to (ZX)-(1).11 aA-514;
compounds (ZXI)-(1).11aA-1 to (ZXI)-(1).11 aA-514;
compounds (ZXII)-(1 ).11 aA-1 to (ZXII)-(1).11 aA-514)
table 12a
Compounds (Z)-(1), wherein A is 3-fluoro-5-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).12aA-1 to (ZI)-(1).12aA-514;
compounds (ZII)-(1).12aA-1 to (ZII)-(1).12aA-514;
compounds (ZIII)-(1).12aA-1 to (ZIII)-(1).12aA-514;
compounds (ZIV)-(1).12aA-1 to (ZIV)-(1).12aA-514;
compounds (ZV)-(1).12aA-1 to (ZV)-(1).12aA-514;
compounds (ZVI)-(1).12aA-1 to (ZVI)-(1).12aA-514;
compounds (ZVII)-(1).12aA-1 to (ZVII)-(1).12aA-514;
compounds (ZVIII)-(1).12aA-1 to (ZVIII)-(1).12aA-514;
compounds (ZIX)-(1).12aA-1 to (ZIX)-(1).12aA-514;
compounds (ZX)-(1).12aA-1 to (ZX)-(1).12aA-514;
compounds (ZXI)-(1).12aA-1 to (ZXI)-(1).12aA-514;
compounds (ZXII)-(1).12aA-1 to (ZXII)-(1).12aA-514)
table 13a
Compounds (Z)-(1), wherein A is 2-chloro-3-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).13aA-1 to (ZI)-(1).13aA-514;
compounds (ZII)-(1).13aA-1 to (ZII)-(1).13aA-514;
compounds (ZIII)-(1).13aA-1 to (ZIII)-(1).13aA-514;
compounds (ZIV)-(1).13aA-1 to (ZIV)-(1).13aA-514;
compounds (ZV)-(1).13aA-1 to (ZV)-(1).13aA-514;
compounds (ZVI)-(1).13aA-1 to (ZVI)-(1).13aA-514;
compounds (ZVII)-(1).13aA-1 to (ZVII)-(1).13aA-514;
compounds (ZVIII)-(1).13aA-1 to (ZVIII)-(1).13aA-514;
compounds (ZIX)-(1).13aA-1 to (ZIX)-(1).13aA-514;
compounds (ZX)-(1).13aA-1 to (ZX)-(1).13aA-514;
compounds (ZXI)-(1).13aA-1 to (ZXI)-(1).13aA-514;
compounds (ZXII)-(1).13aA-1 to (ZXII)-(1).13aA-514)
table 14a
Compounds (Z)-(1), wherein A is 2-chloro-4-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).14aA-1 to (ZI)-(1).14aA-514;
compounds (ZII)-(1).14aA-1 to (ZII)-(1).14aA-514;
compounds (ZIII)-(1).14aA-1 to (ZIII)-(1).14aA-514;
compounds (ZIV)-(1).14aA-1 to (ZIV)-(1).14aA-514;
compounds (ZV)-(1).14aA-1 to (ZV)-(1).14aA-514;
compounds (ZVI)-(1).14aA-1 to (ZVI)-(1).14aA-514;
compounds (ZVII)-(1).14aA-1 to (ZVII)-(1).14aA-514;
compounds (ZVIII)-(1).14aA-1 to (ZVIII)-(1).14aA-514;
compounds (ZIX)-(1).14aA-1 to (ZIX)-(1).14aA-514;
compounds (ZX)-(1).14aA-1 to (ZX)-(1).14aA-514;
compounds (ZXI)-(1).14aA-1 to (ZXI)-(1).14aA-514;
compounds (ZXII)-(1).14aA-1 to (ZXII)-(1).14aA-514)
table 15a
Compounds (Z)-(1), wherein A is 2-chloro-5-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).15aA-1 to (ZI)-(1).15aA-514;
compounds (ZII)-(1).15aA-1 to (ZII)-(1).15aA-514;
compounds (ZIII)-(1).15aA-1 to (ZIII)-(1).15aA-514;
compounds (ZIV)-(1).15aA-1 to (ZIV)-(1).15aA-514;
compounds (ZV)-(1).15aA-1 to (ZV)-(1).15aA-514;
compounds (ZVI)-(1).15aA-1 to (ZVI)-(1).15aA-514;
compounds (ZVII)-(1).15aA-1 to (ZVII)-(1).15aA-514;
compounds (ZVIII)-(1).15aA-1 to (ZVIII)-(1).15aA-514;
compounds (ZIX)-(1).15aA-1 to (ZIX)-(1).15aA-514;
compounds (ZX)-(1).15aA-1 to (ZX)-(1).15aA-514;
compounds (ZXI)-(1).15aA-1 to (ZXI)-(1).15aA-514;
compounds (ZXII)-(1).15aA-1 to (ZXII)-(1).15aA-514)
table 16a
Compounds (Z)-(1), wherein A is 3-chloro-4-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).16aA-1 to (ZI)-(1).16aA-514;
compounds (ZII)-(1).16aA-1 to (ZII)-(1).16aA-514;
compounds (ZIII)-(1).16aA-1 to (ZIII)-(1).16aA-514;
compounds (ZIV)-(1).16aA-1 to (ZIV)-(1).16aA-514;
compounds (ZV)-(1).16aA-1 to (ZV)-(1).16aA-514;
compounds (ZVI)-(1).16aA-1 to (ZVI)-(1).16aA-514;
compounds (ZVII)-(1).16aA-1 to (ZVII)-(1).16aA-514;
compounds (ZVIII)-(1).16aA-1 to (ZVIII)-(1).16aA-514;
compounds (ZIX)-(1).16aA-1 to (ZIX)-(1).16aA-514;
compounds (ZX)-(1).16aA-1 to (ZX)-(1).16aA-514;
compounds (ZXI)-(1).16aA-1 to (ZXI)-(1).16aA-514;
compounds (ZXII)-(1).16aA-1 to (ZXII)-(1).16aA-514)
table 17a
Compounds (Z)-(1), wherein A is 2-methyl-3-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).17aA-1 to (ZI)-(1).17aA-514;
compounds (ZII)-(1).17aA-1 to (ZII)-(1).17aA-514;
compounds (ZIII)-(1).17aA-1 to (ZIII)-(1).17aA-514;
compounds (ZIV)-(1).17aA-1 to (ZIV)-(1).17aA-514;
compounds (ZV)-(1).17aA-1 to (ZV)-(1).17aA-514;
compounds (ZVI)-(1).17aA-1 to (ZVI)-(1).17aA-514;
compounds (ZVII)-(1).17aA-1 to (ZVII)-(1).17aA-514;
compounds (ZVIII)-(1).17aA-1 to (ZVIII)-(1).17aA-514;
compounds (ZIX)-(1).17aA-1 to (ZIX)-(1).17aA-514;
compounds (ZX)-(1).17aA-1 to (ZX)-(1).17aA-514;
compounds (ZXI)-(1).17aA-1 to (ZXI)-(1).17aA-514;
compounds (ZXII)-(1).17aA-1 to (ZXII)-(1).17aA-514)
table 18a
Compounds (Z)-(1), wherein A is 2-methyl-4-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).18aA-1 to (ZI)-(1).18aA-514;
compounds (ZII)-(1).18aA-1 to (ZII)-(1).18aA-514;
compounds (ZIII)-(1).18aA-1 to (ZIII)-(1).18aA-514;
compounds (ZIV)-(1).18aA-1 to (ZIV)-(1).18aA-514;
compounds (ZV)-(1).18aA-1 to (ZV)-(1).18aA-514;
compounds (ZVI)-(1).18aA-1 to (ZVI)-(1).18aA-514;
compounds (ZVII)-(1).18aA-1 to (ZVII)-(1).18aA-514;
compounds (ZVIII)-(1).18aA-1 to (ZVIII)-(1).18aA-514;
compounds (ZIX)-(1).18aA-1 to (ZIX)-(1).18aA-514;
compounds (ZX)-(1).18aA-1 to (ZX)-(1).18aA-514;
compounds (ZXI)-(1).18aA-1 to (ZXI)-(1).18aA-514;
compounds (ZXII)-(1).18aA-1 to (ZXII)-(1).18aA-514)
table 19a
Compounds (Z)-(1), wherein A is 2-methyl-5-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).19aA-1 to (ZI)-(1).19aA-514;
compounds (ZII)-(1).19aA-1 to (ZII)-(1).19aA-514;
compounds (ZIII)-(1).19aA-1 to (ZIII)-(1).19aA-514;
compounds (ZIV)-(1).19aA-1 to (ZIV)-(1).19aA-514;
compounds (ZV)-(1).19aA-1 to (ZV)-(1).19aA-514;
compounds (ZVI)-(1).19aA-1 to (ZVI)-(1).19aA-514;
compounds (ZVII)-(1).19aA-1 to (ZVII)-(1).19aA-514;
compounds (ZVIII)-(1).19aA-1 to (ZVIII)-(1).19aA-514;
compounds (ZIX)-(1).19aA-1 to (ZIX)-(1).19aA-514;
compounds (ZX)-(1).19aA-1 to (ZX)-(1).19aA-514;
compounds (ZXI)-(1).19aA-1 to (ZXI)-(1).19aA-514;
compounds (ZXII)-(1).19aA-1 to (ZXII)-(1).19aA-514)
table 20a
Compounds (Z)-(1), wherein A is 2-methyl-6-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).20aA-1 to (ZI)-(1).20aA-514;
compounds (ZII)-(1).20aA-1 to (ZII)-(1).20aA-514;
compounds (ZIII)-(1).20aA-1 to (ZIII)-(1).20aA-514;
compounds (ZIV)-(1).20aA-1 to (ZIV)-(1).20aA-514;
compounds (ZV)-(1 ).20aA-1 to (ZV)-(1 ).20aA-514;
compounds (ZVI)-(1).20aA-1 to (ZVI)-(1).20aA-514;
compounds (ZVII)-(1).20aA-1 to (ZVII)-(1).20aA-514;
compounds (ZVIII)-(1).20aA-1 to (ZVIII)-(1).20aA-514;
compounds (ZIX)-(1).20aA-1 to (ZIX)-(1).20aA-514;
compounds (ZX)-(1 ).20aA-1 to (ZX)-(1 ).20aA-514;
compounds (ZXI)-(1).20aA-1 to (ZXI)-(1).20aA-514;
compounds (ZXII)-(1).20aA-1 to (ZXII)-(1).20aA-514)
table 21a
Compounds (Z)-(1), wherein A is 3-methyl-4-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).21aA-1 to (ZI)-(1).21aA-514;
compounds (ZII)-(1).21aA-1 to (Zll)-(1 ).21 aA-514;
compounds (ZIII)-(1).21aA-1 to (ZIII)-(1).21aA-514;
compounds (ZIV)-(1).21aA-1 to (ZIV)-(1).21aA-514;
compounds (ZV)-(1).21aA-1 to (ZV)-(1).21aA-514;
compounds (ZVI)-(1).21aA-1 to (ZVI)-(1).21aA-514;
compounds (ZVII)-(1).21aA-1 to (ZVII)-(1).21aA-514;
compounds (ZVIII)-(1).21aA-1 to (ZVIII)-(1).21aA-514;
compounds (ZIX)-(1).21aA-1 to (ZIX)-(1).21aA-514;
compounds (ZX)-(1).21aA-1 to (ZX)-(1).21aA-514;
compounds (ZXI)-(1).21aA-1 to (ZXI)-(1).21aA-514;
compounds (ZXII)-(1).21aA-1 to (ZXII)-(1).21aA-514)
table 22a
Compounds (Z)-(1), wherein A is 3-methyl-5-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).22aA-1 to (ZI)-(1).22aA-514;
compounds (ZII)-(1).22aA-1 to (ZII)-(1).22aA-514;
compounds (ZIII)-(1).22aA-1 to (ZIII)-(1).22aA-514;
compounds (ZIV)-(1).22aA-1 to (ZIV)-(1).22aA-514;
compounds (ZV)-(1).22aA-1 to (ZV)-(1).22aA-514;
compounds (ZVI)-(1).22aA-1 to (ZVI)-(1).22aA-514;
compounds (ZVII)-(1).22aA-1 to (ZVII)-(1).22aA-514;
compounds (ZVIII)-(1).22aA-1 to (ZVIII)-(1).22aA-514;
compounds (ZIX)-(1).22aA-1 to (ZIX)-(1).22aA-514;
compounds (ZX)-(1).22aA-1 to (ZX)-(1).22aA-514;
compounds (ZXI)-(1).22aA-1 to (ZXI)-(1).22aA-514;
compounds (ZXII)-(1).22aA-1 to (ZXII)-(1).22aA-514)
table 23a
Compounds (Z)-(1), wherein A is 2-fluoro-3-methylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).23aA-1 to (ZI)-(1).23aA-514;
compounds (ZII)-(1).23aA-1 to (ZII)-(1).23aA-514;
compounds (ZIII)-(1).23aA-1 to (ZIII)-(1).23aA-514;
compounds (ZIV)-(1).23aA-1 to (ZIV)-(1).23aA-514;
compounds (ZV)-(1 ).23aA-1 to (ZV)-(1 ).23aA-514;
compounds (ZVI)-(1).23aA-1 to (ZVI)-(1).23aA-514;
compounds (ZVII)-(1).23aA-1 to (ZVII)-(1).23aA-514;
compounds (ZVIII)-(1).23aA-1 to (ZVIII)-(1).23aA-514;
compounds (ZIX)-(1).23aA-1 to (ZIX)-(1).23aA-514;
compounds (ZX)-(1 ).23aA-1 to (ZX)-(1 ).23aA-514;
compounds (ZXI)-(1).23aA-1 to (ZXI)-(1).23aA-514;
compounds (ZXII)-(1).23aA-1 to (ZXII)-(1).23aA-514)
table 24a
Compounds (Z)-(1), wherein A is 2-fluoro-4-methylphenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).24aA-1 to (Zl)-(1 ).24aA-514;
compounds (ZII)-(1).24aA-1 to (ZII)-(1).24aA-514;
compounds (ZIII)-(1).24aA-1 to (ZIII)-(1).24aA-514;
compounds (ZIV)-(1).24aA-1 to (ZIV)-(1).24aA-514;
compounds (ZV)-(1).24aA-1 to (ZV)-(1).24aA-514;
compounds (ZVI)-(1).24aA-1 to (ZVI)-(1).24aA-514;
compounds (ZVII)-(1).24aA-1 to (ZVII)-(1).24aA-514;
compounds (ZVIII)-(1).24aA-1 to (ZVIII)-(1).24aA-514;
compounds (ZIX)-(1).24aA-1 to (ZIX)-(1).24aA-514;
compounds (ZX)-(1).24aA-1 to (ZX)-(1).24aA-514;
compounds (ZXI)-(1).24aA-1 to (ZXI)-(1).24aA-514;
compounds (ZXII)-(1).24aA-1 to (ZXII)-(1).24aA-514)
table 25a
Compounds (Z)-(1), wherein A is 2-fluoro-5-methylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).25aA-1 to (ZI)-(1).25aA-514;
compounds (ZII)-(1).25aA-1 to (ZII)-(1).25aA-514;
compounds (ZIII)-(1).25aA-1 to (ZIII)-(1).25aA-514;
compounds (ZIV)-(1).25aA-1 to (ZIV)-(1).25aA-514;
compounds (ZV)-(1).25aA-1 to (ZV)-(1).25aA-514;
compounds (ZVI)-(1).25aA-1 to (ZVI)-(1).25aA-514;
compounds (ZVII)-(1).25aA-1 to (ZVII)-(1).25aA-514;
compounds (ZVIII)-(1).25aA-1 to (ZVIII)-(1).25aA-514;
compounds (ZIX)-(1).25aA-1 to (ZIX)-(1).25aA-514;
compounds (ZX)-(1).25aA-1 to (ZX)-(1).25aA-514;
compounds (ZXI)-(1).25aA-1 to (ZXI)-(1).25aA-514;
compounds (ZXII)-(1).25aA-1 to (ZXII)-(1).25aA-514)
table 26a
Compounds (Z)-(1), wherein A is 3-fluoro-4-methylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).26aA-1 to (ZI)-(1).26aA-514;
compounds (ZII)-(1).26aA-1 to (ZII)-(1).26aA-514;
compounds (ZIII)-(1).26aA-1 to (ZIII)-(1).26aA-514;
compounds (ZIV)-(1).26aA-1 to (ZIV)-(1).26aA-514;
compounds (ZV)-(1 ).26aA-1 to (ZV)-(1 ).26aA-514;
compounds (ZVI)-(1).26aA-1 to (ZVI)-(1).26aA-514;
compounds (ZVII)-(1).26aA-1 to (ZVII)-(1).26aA-514;
compounds (ZVIII)-(1).26aA-1 to (ZVIII)-(1).26aA-514;
compounds (ZIX)-(1).26aA-1 to (ZIX)-(1).26aA-514;
compounds (ZX)-(1 ).26aA-1 to (ZX)-(1 ).26aA-514;
compounds (ZXI)-(1).26aA-1 to (ZXI)-(1).26aA-514;
compounds (ZXII)-(1).26aA-1 to (ZXII)-(1).26aA-514)
table 27a
Compounds (Z)-(1), wherein A is 2-ethyl-3-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).27aA-1 to (ZI)-(1).27aA-514;
compounds (ZII)-(1).27aA-1 to (ZII)-(1).27aA-514;
compounds (ZIII)-(1).27aA-1 to (ZIII)-(1).27aA-514;
compounds (ZIV)-(1).27aA-1 to (ZIV)-(1).27aA-514;
compounds (ZV)-(1).27aA-1 to (ZV)-(1).27aA-514;
compounds (ZVI)-(1).27aA-1 to (ZVI)-(1).27aA-514;
compounds (ZVII)-(1).27aA-1 to (ZVII)-(1).27aA-514;
compounds (ZVIII)-(1).27aA-1 to (ZVIII)-(1).27aA-514;
compounds (ZIX)-(1).27aA-1 to (ZIX)-(1).27aA-514;
compounds (ZX)-(1).27aA-1 to (ZX)-(1).27aA-514;
compounds (ZXI)-(1).27aA-1 to (ZXI)-(1).27aA-514;
compounds (ZXII)-(1).27aA-1 to (ZXII)-(1).27aA-514)
table 28a
Compounds (Z)-(1), wherein A is 2-ethyl-4-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).28aA-1 to (ZI)-(1).28aA-514;
compounds (ZII)-(1).28aA-1 to (ZII)-(1).28aA-514;
compounds (ZIII)-(1).28aA-1 to (ZIII)-(1).28aA-514;
compounds (ZIV)-(1).28aA-1 to (ZIV)-(1).28aA-514;
compounds (ZV)-(1).28aA-1 to (ZV)-(1).28aA-514;
compounds (ZVI)-(1).28aA-1 to (ZVI)-(1).28aA-514;
compounds (ZVII)-(1).28aA-1 to (ZVII)-(1).28aA-514;
compounds (ZVIII)-(1).28aA-1 to (ZVIII)-(1).28aA-514;
compounds (ZIX)-(1).28aA-1 to (ZIX)-(1).28aA-514;
compounds (ZX)-(1).28aA-1 to (ZX)-(1).28aA-514;
compounds (ZXI)-(1).28aA-1 to (ZXI)-(1).28aA-514;
compounds (ZXII)-(1).28aA-1 to (ZXII)-(1).28aA-514)
table 29a
Compounds (Z)-(1), wherein A is 2-ethyl-5-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).29aA-1 to (ZI)-(1).29aA-514;
compounds (ZII)-(1).29aA-1 to (ZII)-(1).29aA-514;
compounds (ZIII)-(1).29aA-1 to (ZIII)-(1).29aA-514;
compounds (ZIV)-(1).29aA-1 to (ZIV)-(1).29aA-514;
compounds (ZV)-(1 ).29aA-1 to (ZV)-(1 ).29aA-514;
compounds (ZVI)-(1).29aA-1 to (ZVI)-(1).29aA-514;
compounds (ZVII)-(1).29aA-1 to (ZVII)-(1).29aA-514;
compounds (ZVIII)-(1).29aA-1 to (ZVIII)-(1).29aA-514;
compounds (ZIX)-(1).29aA-1 to (ZIX)-(1).29aA-514;
compounds (ZX)-(1 ).29aA-1 to (ZX)-(1 ).29aA-514;
compounds (ZXI)-(1).29aA-1 to (ZXI)-(1).29aA-514;
compounds (ZXII)-(1).29aA-1 to (ZXII)-(1).29aA-514)
table 30a
Compounds (Z)-(1), wherein A is 2-ethyl-6-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).30aA-1 to (ZI)-(1).30aA-514;
compounds (ZII)-(1).30aA-1 to (ZII)-(1).30aA-514;
compounds (ZIII)-(1).30aA-1 to (ZIII)-(1).30aA-514;
compounds (ZIV)-(1).30aA-1 to (ZIV)-(1).30aA-514;
compounds (ZV)-(1).30aA-1 to (ZV)-(1).30aA-514;
compounds (ZVI)-(1).30aA-1 to (ZVI)-(1).30aA-514;
compounds (ZVII)-(1).30aA-1 to (ZVII)-(1).30aA-514;
compounds (ZVIII)-(1).30aA-1 to (ZVIII)-(1).30aA-514;
compounds (ZIX)-(1).30aA-1 to (ZIX)-(1).30aA-514;
compounds (ZX)-(1).30aA-1 to (ZX)-(1).30aA-514;
compounds (ZXI)-(1).30aA-1 to (ZXI)-(1).30aA-514;
compounds (ZXII)-(1).30aA-1 to (ZXII)-(1).30aA-514)
table 31a
Compounds (Z)-(1), wherein A is 3-ethyl-4-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).31aA-1 to (ZI)-(1).31aA-514;
compounds (ZII)-(1).31aA-1 to (Zll)-(1 ).31 aA-514;
compounds (ZIII)-(1).31aA-1 to (ZIII)-(1).31aA-514;
compounds (ZIV)-(1).31aA-1 to (ZIV)-(1).31aA-514;
compounds (ZV)-(1).31aA-1 to (ZV)-(1).31aA-514;
compounds (ZVI)-(1).31aA-1 to (ZVI)-(1).31aA-514;
compounds (ZVII)-(1).31aA-1 to (ZVII)-(1).31aA-514;
compounds (ZVIII)-(1).31aA-1 to (ZVIII)-(1).31aA-514;
compounds (ZIX)-(1).31aA-1 to (ZIX)-(1).31aA-514;
compounds (ZX)-(1).31aA-1 to (ZX)-(1).31aA-514;
compounds (ZXI)-(1).31aA-1 to (ZXI)-(1).31aA-514;
compounds (ZXII)-(1).31aA-1 to (ZXII)-(1).31aA-514)
table 32a
Compounds (Z)-(1), wherein A is 3-ethyl-5-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).32aA-1 to (ZI)-(1).32aA-514;
compounds (ZII)-(1).32aA-1 to (ZII)-(1).32aA-514;
compounds (ZIII)-(1).32aA-1 to (ZIII)-(1).32aA-514;
compounds (ZIV)-(1).32aA-1 to (ZIV)-(1).32aA-514;
compounds (ZV)-(1 ).32aA-1 to (ZV)-(1 ).32aA-514;
compounds (ZVI)-(1).32aA-1 to (ZVI)-(1).32aA-514;
compounds (ZVII)-(1).32aA-1 to (ZVII)-(1).32aA-514;
compounds (ZVIII)-(1).32aA-1 to (ZVIII)-(1).32aA-514;
compounds (ZIX)-(1).32aA-1 to (ZIX)-(1).32aA-514;
compounds (ZX)-(1 ).32aA-1 to (ZX)-(1 ).32aA-514;
compounds (ZXI)-(1).32aA-1 to (ZXI)-(1).32aA-514;
compounds (ZXII)-(1).32aA-1 to (ZXII)-(1).32aA-514)
table 33a
Compounds (Z)-(1), wherein A is 2-fluoro-3-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).33aA-1 to (ZI)-(1).33aA-514;
compounds (ZII)-(1).33aA-1 to (ZII)-(1).33aA-514;
compounds (ZIII)-(1).33aA-1 to (ZIII)-(1).33aA-514;
compounds (ZIV)-(1).33aA-1 to (ZIV)-(1).33aA-514;
compounds (ZV)-(1).33aA-1 to (ZV)-(1).33aA-514;
compounds (ZVI)-(1).33aA-1 to (ZVI)-(1).33aA-514;
compounds (ZVII)-(1).33aA-1 to (ZVII)-(1).33aA-514;
compounds (ZVIII)-(1).33aA-1 to (ZVIII)-(1).33aA-514;
compounds (ZIX)-(1).33aA-1 to (ZIX)-(1).33aA-514;
compounds (ZX)-(1).33aA-1 to (ZX)-(1).33aA-514;
compounds (ZXI)-(1).33aA-1 to (ZXI)-(1).33aA-514;
compounds (ZXII)-(1).33aA-1 to (ZXII)-(1).33aA-514)
table 34a
Compounds (Z)-(1), wherein A is 2-fluoro-4-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).34aA-1 to (ZI)-(1).34aA-514;
compounds (ZII)-(1).34aA-1 to (ZII)-(1).34aA-514;
compounds (ZIII)-(1).34aA-1 to (ZIII)-(1).34aA-514;
compounds (ZIV)-(1).34aA-1 to (ZIV)-(1).34aA-514;
compounds (ZV)-(1).34aA-1 to (ZV)-(1).34aA-514;
compounds (ZVI)-(1).34aA-1 to (ZVI)-(1).34aA-514;
compounds (ZVII)-(1).34aA-1 to (ZVII)-(1).34aA-514;
compounds (ZVIII)-(1).34aA-1 to (ZVIII)-(1).34aA-514;
compounds (ZIX)-(1).34aA-1 to (ZIX)-(1).34aA-514;
compounds (ZX)-(1).34aA-1 to (ZX)-(1).34aA-514;
compounds (ZXI)-(1).34aA-1 to (ZXI)-(1).34aA-514;
compounds (ZXII)-(1).34aA-1 to (ZXII)-(1).34aA-514)
table 35a
Compounds (Z)-(1), wherein A is 2-fluoro-5-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).35aA-1 to (ZI)-(1).35aA-514;
compounds (ZII)-(1).35aA-1 to (ZII)-(1).35aA-514;
compounds (ZIII)-(1).35aA-1 to (ZIII)-(1).35aA-514;
compounds (ZIV)-(1).35aA-1 to (ZIV)-(1).35aA-514;
compounds (ZV)-(1 ).35aA-1 to (ZV)-(1 ).35aA-514;
compounds (ZVI)-(1).35aA-1 to (ZVI)-(1).35aA-514;
compounds (ZVII)-(1).35aA-1 to (ZVII)-(1).35aA-514;
compounds (ZVIII)-(1).35aA-1 to (ZVIII)-(1).35aA-514;
compounds (ZIX)-(1).35aA-1 to (ZIX)-(1).35aA-514;
compounds (ZX)-(1 ).35aA-1 to (ZX)-(1 ).35aA-514;
compounds (ZXI)-(1).35aA-1 to (ZXI)-(1).35aA-514;
compounds (ZXII)-(1).35aA-1 to (ZXII)-(1).35aA-514)
table 36a
Compounds (Z)-(1), wherein A is 3-fluoro-4-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).36aA-1 to (ZI)-(1).36aA-514;
compounds (ZII)-(1).36aA-1 to (ZII)-(1).36aA-514;
compounds (ZIII)-(1).36aA-1 to (ZIII)-(1).36aA-514;
compounds (ZIV)-(1).36aA-1 to (ZIV)-(1).36aA-514;
compounds (ZV)-(1).36aA-1 to (ZV)-(1).36aA-514;
compounds (ZVI)-(1).36aA-1 to (ZVI)-(1).36aA-514;
compounds (ZVII)-(1).36aA-1 to (ZVII)-(1).36aA-514;
compounds (ZVIII)-(1).36aA-1 to (ZVIII)-(1).36aA-514;
compounds (ZIX)-(1).36aA-1 to (ZIX)-(1).36aA-514;
compounds (ZX)-(1).36aA-1 to (ZX)-(1).36aA-514;
compounds (ZXI)-(1).36aA-1 to (ZXI)-(1).36aA-514;
compounds (ZXII)-(1).36aA-1 to (ZXII)-(1).36aA-514)
table 37a
Compounds (Z)-(1), wherein A is 2-methoxy-3-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).37aA-1 to (ZI)-(1).37aA-514;
compounds (ZII)-(1).37aA-1 to (ZII)-(1).37aA-514;
compounds (ZIII)-(1).37aA-1 to (ZIII)-(1).37aA-514;
compounds (ZIV)-(1).37aA-1 to (ZIV)-(1).37aA-514;
compounds (ZV)-(1).37aA-1 to (ZV)-(1).37aA-514;
compounds (ZVI)-(1).37aA-1 to (ZVI)-(1).37aA-514;
compounds (ZVII)-(1).37aA-1 to (ZVII)-(1).37aA-514;
compounds (ZVIII)-(1).37aA-1 to (ZVIII)-(1).37aA-514;
compounds (ZIX)-(1).37aA-1 to (ZIX)-(1).37aA-514;
compounds (ZX)-(1).37aA-1 to (ZX)-(1).37aA-514;
compounds (ZXI)-(1).37aA-1 to (ZXI)-(1).37aA-514;
compounds (ZXII)-(1).37aA-1 to (ZXII)-(1).37aA-514)
table 38a
Compounds (Z)-(1), wherein A is 2-methoxy-4-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).38aA-1 to (ZI)-(1).38aA-514;
compounds (ZII)-(1).38aA-1 to (ZII)-(1).38aA-514;
compounds (ZIII)-(1).38aA-1 to (ZIII)-(1).38aA-514;
compounds (ZIV)-(1).38aA-1 to (ZIV)-(1).38aA-514;
compounds (ZV)-(1 ).38aA-1 to (ZV)-(1 ).38aA-514;
compounds (ZVI)-(1).38aA-1 to (ZVI)-(1).38aA-514;
compounds (ZVII)-(1).38aA-1 to (ZVII)-(1).38aA-514;
compounds (ZVIII)-(1).38aA-1 to (ZVIII)-(1).38aA-514;
compounds (ZIX)-(1).38aA-1 to (ZIX)-(1).38aA-514;
compounds (ZX)-(1 ).38aA-1 to (ZX)-(1 ).38aA-514;
compounds (ZXI)-(1).38aA-1 to (ZXI)-(1).38aA-514;
compounds (ZXII)-(1).38aA-1 to (ZXII)-(1).38aA-514)
table 39a
Compounds (Z)-(1), wherein A is 2-methoxy-5-fluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).39aA-1 to (Zl)-(1 ).39aA-514;
compounds (ZII)-(1).39aA-1 to (ZII)-(1).39aA-514;
compounds (ZIII)-(1).39aA-1 to (ZIII)-(1).39aA-514;
compounds (ZIV)-(1).39aA-1 to (ZIV)-(1).39aA-514;
compounds (ZV)-(1).39aA-1 to (ZV)-(1).39aA-514;
compounds (ZVI)-(1).39aA-1 to (ZVI)-(1).39aA-514;
compounds (ZVII)-(1).39aA-1 to (ZVII)-(1).39aA-514;
compounds (ZVIII)-(1).39aA-1 to (ZVIII)-(1).39aA-514;
compounds (ZIX)-(1).39aA-1 to (ZIX)-(1).39aA-514;
compounds (ZX)-(1).39aA-1 to (ZX)-(1).39aA-514;
compounds (ZXI)-(1).39aA-1 to (ZXI)-(1).39aA-514;
compounds (ZXII)-(1).39aA-1 to (ZXII)-(1).39aA-514)
table 40a
Compounds (Z)-(1), wherein A is 2-methoxy-6-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).40aA-1 to (ZI)-(1).40aA-514;
compounds (ZII)-(1).40aA-1 to (ZII)-(1).40aA-514;
compounds (ZIII)-(1).40aA-1 to (ZIII)-(1).40aA-514;
compounds (ZIV)-(1).40aA-1 to (ZIV)-(1).40aA-514;
compounds (ZV)-(1).40aA-1 to (ZV)-(1).40aA-514;
compounds (ZVI)-(1).40aA-1 to (ZVI)-(1).40aA-514;
compounds (ZVII)-(1).40aA-1 to (ZVII)-(1).40aA-514;
compounds (ZVIII)-(1).40aA-1 to (ZVIII)-(1).40aA-514;
compounds (ZIX)-(1).40aA-1 to (ZIX)-(1).40aA-514;
compounds (ZX)-(1).40aA-1 to (ZX)-(1).40aA-514;
compounds (ZXI)-(1).40aA-1 to (ZXI)-(1).40aA-514;
compounds (ZXII)-(1).40aA-1 to (ZXII)-(1).40aA-514)
table 41a
Compounds (Z)-(1), wherein A is 3-methoxy-4-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).41aA-1 to (ZI)-(1).41aA-514;
compounds (ZII)-(1).41aA-1 to (Zll)-(1 ).41 aA-514;
compounds (ZIII)-(1).41aA-1 to (ZIII)-(1).41aA-514;
compounds (ZIV)-(1).41aA-1 to (ZIV)-(1).41aA-514;
compounds (ZV)-(1).41aA-1 to (ZV)-(1).41aA-514;
compounds (ZVI)-(1).41aA-1 to (ZVI)-(1).41aA-514;
compounds (ZVII)-(1).41aA-1 to (ZVII)-(1).41aA-514;
compounds (ZVIII)-(1).41aA-1 to (ZVIII)-(1).41aA-514;
compounds (ZIX)-(1).41aA-1 to (ZIX)-(1).41aA-514;
compounds (ZX)-(1).41aA-1 to (ZX)-(1).41aA-514;
compounds (ZXI)-(1).41aA-1 to (ZXI)-(1).41aA-514;
compounds (ZXII)-(1).41aA-1 to (ZXII)-(1).41aA-514)
table 42a
Compounds (Z)-(1), wherein A is 3-methoxy-5-fluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).42aA-1 to (Zl)-(1 ).42aA-514;
compounds (ZII)-(1).42aA-1 to (ZII)-(1).42aA-514;
compounds (ZIII)-(1).42aA-1 to (ZIII)-(1).42aA-514;
compounds (ZIV)-(1).42aA-1 to (ZIV)-(1).42aA-514;
compounds (ZV)-(1).42aA-1 to (ZV)-(1).42aA-514;
compounds (ZVI)-(1).42aA-1 to (ZVI)-(1).42aA-514;
compounds (ZVII)-(1).42aA-1 to (ZVII)-(1).42aA-514;
compounds (ZVIII)-(1).42aA-1 to (ZVIII)-(1).42aA-514;
compounds (ZIX)-(1).42aA-1 to (ZIX)-(1).42aA-514;
compounds (ZX)-(1).42aA-1 to (ZX)-(1).42aA-514;
compounds (ZXI)-(1).42aA-1 to (ZXI)-(1).42aA-514;
compounds (ZXII)-(1).42aA-1 to (ZXII)-(1).42aA-514)
table 43a
Compounds (Z)-(1), wherein A is 2-fluoro-3-methoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).43aA-1 to (ZI)-(1).43aA-514;
compounds (ZII)-(1).43aA-1 to (ZII)-(1).43aA-514;
compounds (ZIII)-(1).43aA-1 to (ZIII)-(1).43aA-514;
compounds (ZIV)-(1).43aA-1 to (ZIV)-(1).43aA-514;
compounds (ZV)-(1).43aA-1 to (ZV)-(1).43aA-514;
compounds (ZVI)-(1).43aA-1 to (ZVI)-(1).43aA-514;
compounds (ZVII)-(1).43aA-1 to (ZVII)-(1).43aA-514;
compounds (ZVIII)-(1).43aA-1 to (ZVIII)-(1).43aA-514;
compounds (ZIX)-(1).43aA-1 to (ZIX)-(1).43aA-514;
compounds (ZX)-(1).43aA-1 to (ZX)-(1).43aA-514;
compounds (ZXI)-(1).43aA-1 to (ZXI)-(1).43aA-514;
compounds (ZXII)-(1).43aA-1 to (ZXII)-(1).43aA-514)
table 44a
Compounds (Z)-(1), wherein A is 2-fluoro-4-methoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).44aA-1 to (ZI)-(1).44aA-514;
compounds (ZII)-(1).44aA-1 to (ZII)-(1).44aA-514;
compounds (ZIII)-(1).44aA-1 to (ZIII)-(1).44aA-514;
compounds (ZIV)-(1).44aA-1 to (ZIV)-(1).44aA-514;
compounds (ZV)-(1 ).44aA-1 to (ZV)-(1 ).44aA-514;
compounds (ZVI)-(1).44aA-1 to (ZVI)-(1).44aA-514;
compounds (ZVII)-(1).44aA-1 to (ZVII)-(1).44aA-514;
compounds (ZVIII)-(1).44aA-1 to (ZVIII)-(1).44aA-514;
compounds (ZIX)-(1).44aA-1 to (ZIX)-(1).44aA-514;
compounds (ZX)-(1 ).44aA-1 to (ZX)-(1 ).44aA-514;
compounds (ZXI)-(1).44aA-1 to (ZXI)-(1).44aA-514;
compounds (ZXII)-(1).44aA-1 to (ZXII)-(1).44aA-514)
table 45a
Compounds (Z)-(1), wherein A is 2-fluoro-5-methoxyphenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).45aA-1 to (Zl)-(1 ).45aA-514;
compounds (ZII)-(1).45aA-1 to (ZII)-(1).45aA-514;
compounds (ZIII)-(1).45aA-1 to (ZIII)-(1).45aA-514;
compounds (ZIV)-(1).45aA-1 to (ZIV)-(1).45aA-514;
compounds (ZV)-(1).45aA-1 to (ZV)-(1).45aA-514;
compounds (ZVI)-(1).45aA-1 to (ZVI)-(1).45aA-514;
compounds (ZVII)-(1).45aA-1 to (ZVII)-(1).45aA-514;
compounds (ZVIII)-(1).45aA-1 to (ZVIII)-(1).45aA-514;
compounds (ZIX)-(1).45aA-1 to (ZIX)-(1).45aA-514;
compounds (ZX)-(1).45aA-1 to (ZX)-(1).45aA-514;
compounds (ZXI)-(1).45aA-1 to (ZXI)-(1).45aA-514;
compounds (ZXII)-(1).45aA-1 to (ZXII)-(1).45aA-514)
table 46a
Compounds (Z)-(1), wherein A is 3-fluoro-4-methoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).46aA-1 to (ZI)-(1).46aA-514;
compounds (ZII)-(1).46aA-1 to (ZII)-(1).46aA-514;
compounds (ZIII)-(1).46aA-1 to (ZIII)-(1).46aA-514;
compounds (ZIV)-(1).46aA-1 to (ZIV)-(1).46aA-514;
compounds (ZV)-(1).46aA-1 to (ZV)-(1).46aA-514;
compounds (ZVI)-(1).46aA-1 to (ZVI)-(1).46aA-514;
compounds (ZVII)-(1).46aA-1 to (ZVII)-(1).46aA-514;
compounds (ZVIII)-(1).46aA-1 to (ZVIII)-(1).46aA-514;
compounds (ZIX)-(1).46aA-1 to (ZIX)-(1).46aA-514;
compounds (ZX)-(1).46aA-1 to (ZX)-(1).46aA-514;
compounds (ZXI)-(1).46aA-1 to (ZXI)-(1).46aA-514;
compounds (ZXII)-(1).46aA-1 to (ZXII)-(1).46aA-514)
table 47a
Compounds (Z)-(1), wherein A is 3-fluoro-5-methoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).47aA-1 to (ZI)-(1).47aA-514;
compounds (ZII)-(1).47aA-1 to (ZII)-(1).47aA-514;
compounds (ZIII)-(1).47aA-1 to (ZIII)-(1).47aA-514;
compounds (ZIV)-(1).47aA-1 to (ZIV)-(1).47aA-514;
compounds (ZV)-(1 ).47aA-1 to (ZV)-(1 ).47aA-514;
compounds (ZVI)-(1).47aA-1 to (ZVI)-(1).47aA-514;
compounds (ZVII)-(1).47aA-1 to (ZVII)-(1).47aA-514;
compounds (ZVIII)-(1).47aA-1 to (ZVIII)-(1).47aA-514;
compounds (ZIX)-(1).47aA-1 to (ZIX)-(1).47aA-514;
compounds (ZX)-(1 ).47aA-1 to (ZX)-(1 ).47aA-514;
compounds (ZXI)-(1).47aA-1 to (ZXI)-(1).47aA-514;
compounds (ZXII)-(1).47aA-1 to (ZXII)-(1).47aA-514)
table 48a
Compounds (Z)-(1), wherein A is 2-(trifluoromethyl)-3-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).48aA-1 to (Zl)-(1 ).48aA-514; compounds (ZII)-(1).48aA-1 to (ZII)-(1).48aA-514;
compounds (ZIII)-(1).48aA-1 to (ZIII)-(1).48aA-514;
compounds (ZIV)-(1).48aA-1 to (ZIV)-(1).48aA-514;
compounds (ZV)-(1).48aA-1 to (ZV)-(1).48aA-514;
compounds (ZVI)-(1).48aA-1 to (ZVI)-(1).48aA-514;
compounds (ZVII)-(1).48aA-1 to (ZVII)-(1).48aA-514;
compounds (ZVIII)-(1).48aA-1 to (ZVIII)-(1).48aA-514;
compounds (ZIX)-(1).48aA-1 to (ZIX)-(1).48aA-514;
compounds (ZX)-(1).48aA-1 to (ZX)-(1).48aA-514;
compounds (ZXI)-(1).48aA-1 to (ZXI)-(1).48aA-514;
compounds (ZXII)-(1).48aA-1 to (ZXII)-(1).48aA-514)
table 49a
Compounds (Z)-(1), wherein A is 2-(trifluoromethyl)-4-fluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).49aA-1 to (Zl)-(1 ).49aA-514; compounds (ZII)-(1).49aA-1 to (ZII)-(1).49aA-514;
compounds (ZIII)-(1).49aA-1 to (ZIII)-(1).49aA-514;
compounds (ZIV)-(1).49aA-1 to (ZIV)-(1).49aA-514;
compounds (ZV)-(1).49aA-1 to (ZV)-(1).49aA-514;
compounds (ZVI)-(1).49aA-1 to (ZVI)-(1).49aA-514;
compounds (ZVII)-(1).49aA-1 to (ZVII)-(1).49aA-514;
compounds (ZVIII)-(1).49aA-1 to (ZVIII)-(1).49aA-514;
compounds (ZIX)-(1).49aA-1 to (ZIX)-(1).49aA-514;
compounds (ZX)-(1).49aA-1 to (ZX)-(1).49aA-514;
compounds (ZXI)-(1).49aA-1 to (ZXI)-(1).49aA-514;
compounds (ZXII)-(1).49aA-1 to (ZXII)-(1).49aA-514)
table 50a
Compounds (Z)-(1), wherein A is 2-(trifluoromethyl)-5-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).50aA-1 to (Zl)-(1 ).50aA-514; compounds (ZII)-(1).50aA-1 to (ZII)-(1).50aA-514;
compounds (ZIII)-(1).50aA-1 to (ZIII)-(1).50aA-514;
compounds (ZIV)-(1).50aA-1 to (ZIV)-(1).50aA-514;
compounds (ZV)-(1 ).50aA-1 to (ZV)-(1 ).50aA-514;
compounds (ZVI)-(1).50aA-1 to (ZVI)-(1).50aA-514;
compounds (ZVII)-(1).50aA-1 to (ZVII)-(1).50aA-514;
compounds (ZVIII)-(1).50aA-1 to (ZVIII)-(1).50aA-514;
compounds (ZIX)-(1).50aA-1 to (ZIX)-(1).50aA-514;
compounds (ZX)-(1 ).50aA-1 to (ZX)-(1 ).50aA-514;
compounds (ZXI)-(1).50aA-1 to (ZXI)-(1).50aA-514;
compounds (ZXII)-(1).50aA-1 to (ZXII)-(1).50aA-514)
table 51a
Compounds (Z)-(1), wherein A is 2-(trifluoromethyl)-6-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).51 aA-1 to (Zl)-(1 ).51 aA-514; compounds (Zll)-(1 ).51 aA-1 to (Zll)-(1 ).51 aA-514;
compounds (ZIII)-(1).51aA-1 to (ZIII)-(1).51aA-514;
compounds (ZIV)-(1).51aA-1 to (ZIV)-(1).51aA-514;
compounds (ZV)-(1).51aA-1 to (ZV)-(1).51aA-514;
compounds (ZVI)-(1).51aA-1 to (ZVI)-(1).51aA-514;
compounds (ZVII)-(1).51aA-1 to (ZVII)-(1).51aA-514;
compounds (ZVIII)-(1).51aA-1 to (ZVIII)-(1).51aA-514;
compounds (ZIX)-(1).51aA-1 to (ZIX)-(1).51aA-514;
compounds (ZX)-(1).51aA-1 to (ZX)-(1).51aA-514;
compounds (ZXI)-(1).51aA-1 to (ZXI)-(1).51aA-514;
compounds (ZXII)-(1).51aA-1 to (ZXII)-(1).51aA-514)
table 52a
Compounds (Z)-(1), wherein A is 3-(trifluoromethyl)-4-fluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).52aA-1 to (Zl)-(1 ).52aA-514; compounds (ZII)-(1).52aA-1 to (ZII)-(1).52aA-514;
compounds (ZIII)-(1).52aA-1 to (ZIII)-(1).52aA-514;
compounds (ZIV)-(1).52aA-1 to (ZIV)-(1).52aA-514;
compounds (ZV)-(1).52aA-1 to (ZV)-(1).52aA-514;
compounds (ZVI)-(1).52aA-1 to (ZVI)-(1).52aA-514;
compounds (ZVII)-(1).52aA-1 to (ZVII)-(1).52aA-514;
compounds (ZVIII)-(1).52aA-1 to (ZVIII)-(1).52aA-514;
compounds (ZIX)-(1).52aA-1 to (ZIX)-(1).52aA-514;
compounds (ZX)-(1).52aA-1 to (ZX)-(1).52aA-514;
compounds (ZXI)-(1).52aA-1 to (ZXI)-(1).52aA-514;
compounds (ZXII)-(1).52aA-1 to (ZXII)-(1).52aA-514)
table 53a
Compounds (Z)-(1), wherein A is 3-(trifluoromethyl)-5-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).53aA-1 to (Zl)-(1 ).53aA-514; compounds (ZII)-(1).53aA-1 to (ZII)-(1).53aA-514;
compounds (ZIII)-(1).53aA-1 to (ZIII)-(1).53aA-514;
compounds (ZIV)-(1).53aA-1 to (ZIV)-(1).53aA-514;
compounds (ZV)-(1 ).53aA-1 to (ZV)-(1 ).53aA-514;
compounds (ZVI)-(1).53aA-1 to (ZVI)-(1).53aA-514;
compounds (ZVII)-(1).53aA-1 to (ZVII)-(1).53aA-514;
compounds (ZVIII)-(1).53aA-1 to (ZVIII)-(1).53aA-514;
compounds (ZIX)-(1).53aA-1 to (ZIX)-(1).53aA-514;
compounds (ZX)-(1 ).53aA-1 to (ZX)-(1 ).53aA-514;
compounds (ZXI)-(1).53aA-1 to (ZXI)-(1).53aA-514;
compounds (ZXII)-(1).53aA-1 to (ZXII)-(1).53aA-514)
table 54a
Compounds (Z)-(1), wherein A is 2-fluoro-3-(trifluoromethyl)phenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).54aA-1 to (Zl)-(1 ).54aA-514; compounds (ZII)-(1).54aA-1 to (ZII)-(1).54aA-514;
compounds (ZIII)-(1).54aA-1 to (ZIII)-(1).54aA-514;
compounds (ZIV)-(1).54aA-1 to (ZIV)-(1).54aA-514;
compounds (ZV)-(1).54aA-1 to (ZV)-(1).54aA-514;
compounds (ZVI)-(1).54aA-1 to (ZVI)-(1).54aA-514;
compounds (ZVII)-(1).54aA-1 to (ZVII)-(1).54aA-514;
compounds (ZVIII)-(1).54aA-1 to (ZVIII)-(1).54aA-514;
compounds (ZIX)-(1).54aA-1 to (ZIX)-(1).54aA-514;
compounds (ZX)-(1).54aA-1 to (ZX)-(1).54aA-514;
compounds (ZXI)-(1).54aA-1 to (ZXI)-(1).54aA-514;
compounds (ZXII)-(1).54aA-1 to (ZXII)-(1).54aA-514)
table 55a
Compounds (Z)-(1), wherein A is 2-fluoro-4-(trifluoromethyl)phenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).55aA-1 to (Zl)-(1 ).55aA-514; compounds (ZII)-(1).55aA-1 to (ZII)-(1).55aA-514;
compounds (ZIII)-(1).55aA-1 to (ZIII)-(1).55aA-514;
compounds (ZIV)-(1).55aA-1 to (ZIV)-(1).55aA-514;
compounds (ZV)-(1).55aA-1 to (ZV)-(1).55aA-514;
compounds (ZVI)-(1).55aA-1 to (ZVI)-(1).55aA-514;
compounds (ZVII)-(1).55aA-1 to (ZVII)-(1).55aA-514;
compounds (ZVIII)-(1).55aA-1 to (ZVIII)-(1).55aA-514;
compounds (ZIX)-(1).55aA-1 to (ZIX)-(1).55aA-514;
compounds (ZX)-(1).55aA-1 to (ZX)-(1).55aA-514;
compounds (ZXI)-(1).55aA-1 to (ZXI)-(1).55aA-514;
compounds (ZXII)-(1).55aA-1 to (ZXII)-(1).55aA-514)
table 56a
Compounds (Z)-(1), wherein A is 2-fluoro-5-(trifluoromethyl)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).56aA-1 to (ZI)-(1).56aA-514; compounds (ZII)-(1).56aA-1 to (ZII)-(1).56aA-514;
compounds (ZIII)-(1).56aA-1 to (ZIII)-(1).56aA-514;
compounds (ZIV)-(1).56aA-1 to (ZIV)-(1).56aA-514;
compounds (ZV)-(1 ).56aA-1 to (ZV)-(1 ).56aA-514;
compounds (ZVI)-(1).56aA-1 to (ZVI)-(1).56aA-514;
compounds (ZVII)-(1).56aA-1 to (ZVII)-(1).56aA-514;
compounds (ZVIII)-(1).56aA-1 to (ZVIII)-(1).56aA-514;
compounds (ZIX)-(1).56aA-1 to (ZIX)-(1).56aA-514;
compounds (ZX)-(1 ).56aA-1 to (ZX)-(1 ).56aA-514;
compounds (ZXI)-(1).56aA-1 to (ZXI)-(1).56aA-514;
compounds (ZXII)-(1).56aA-1 to (ZXII)-(1).56aA-514)
table 57a
Compounds (Z)-(1), wherein A is 3-fluoro-4-(trifluoromethyl)phenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).57aA-1 to (Zl)-(1 ).57aA-514; compounds (ZII)-(1).57aA-1 to (ZII)-(1).57aA-514;
compounds (ZIII)-(1).57aA-1 to (ZIII)-(1).57aA-514;
compounds (ZIV)-(1).57aA-1 to (ZIV)-(1).57aA-514;
compounds (ZV)-(1).57aA-1 to (ZV)-(1).57aA-514;
compounds (ZVI)-(1 ).57aA-1 to (ZVI)-(1 ).57aA-514;
compounds (ZVII)-(1).57aA-1 to (ZVII)-(1).57aA-514;
compounds (ZVIII)-(1).57aA-1 to (ZVIII)-(1).57aA-514;
compounds (ZIX)-(1).57aA-1 to (ZIX)-(1).57aA-514;
compounds (ZX)-(1).57aA-1 to (ZX)-(1).57aA-514;
compounds (ZXI)-(1).57aA-1 to (ZXI)-(1).57aA-514;
compounds (ZXII)-(1).57aA-1 to (ZXII)-(1).57aA-514)
table 58a
Compounds (Z)-(1), wherein A is 2-(trifluoromethoxy)-3-fluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).58aA-1 to (Zl)-(1 ).58aA-514; compounds (ZII)-(1).58aA-1 to (ZII)-(1).58aA-514;
compounds (ZIII)-(1).58aA-1 to (ZIII)-(1).58aA-514;
compounds (ZIV)-(1).58aA-1 to (ZIV)-(1).58aA-514;
compounds (ZV)-(1).58aA-1 to (ZV)-(1).58aA-514;
compounds (ZVI)-(1).58aA-1 to (ZVI)-(1).58aA-514;
compounds (ZVII)-(1).58aA-1 to (ZVII)-(1).58aA-514;
compounds (ZVIII)-(1).58aA-1 to (ZVIII)-(1).58aA-514;
compounds (ZIX)-(1).58aA-1 to (ZIX)-(1).58aA-514;
compounds (ZX)-(1).58aA-1 to (ZX)-(1).58aA-514;
compounds (ZXI)-(1).58aA-1 to (ZXI)-(1).58aA-514;
compounds (ZXII)-(1).58aA-1 to (ZXII)-(1).58aA-514)
table 59a
Compounds (Z)-(1), wherein A is 2-(trifluoromethoxy)-4-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).59aA-1 to (Zl)-(1 ).59aA-514; compounds (ZII)-(1).59aA-1 to (ZII)-(1).59aA-514;
compounds (ZIII)-(1).59aA-1 to (ZIII)-(1).59aA-514;
compounds (ZIV)-(1).59aA-1 to (ZIV)-(1).59aA-514;
compounds (ZV)-(1 ).59aA-1 to (ZV)-(1 ).59aA-514;
compounds (ZVI)-(1).59aA-1 to (ZVI)-(1).59aA-514;
compounds (ZVII)-(1).59aA-1 to (ZVII)-(1).59aA-514;
compounds (ZVIII)-(1).59aA-1 to (ZVIII)-(1).59aA-514;
compounds (ZIX)-(1).59aA-1 to (ZIX)-(1).59aA-514;
compounds (ZX)-(1 ).59aA-1 to (ZX)-(1 ).59aA-514;
compounds (ZXI)-(1).59aA-1 to (ZXI)-(1).59aA-514;
compounds (ZXII)-(1).59aA-1 to (ZXII)-(1).59aA-514)
table 60a
Compounds (Z)-(1), wherein A is 2-(trifluoromethoxy)-5-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).60aA-1 to (Zl)-(1 ).60aA-514; compounds (ZII)-(1).60aA-1 to (ZII)-(1).60aA-514;
compounds (ZIII)-(1).60aA-1 to (ZIII)-(1).60aA-514;
compounds (ZIV)-(1).60aA-1 to (ZIV)-(1).60aA-514;
compounds (ZV)-(1).60aA-1 to (ZV)-(1).60aA-514;
compounds (ZVI)-(1).60aA-1 to (ZVI)-(1).60aA-514;
compounds (ZVII)-(1).60aA-1 to (ZVII)-(1).60aA-514;
compounds (ZVIII)-(1).60aA-1 to (ZVIII)-(1).60aA-514;
compounds (ZIX)-(1).60aA-1 to (ZIX)-(1).60aA-514;
compounds (ZX)-(1).60aA-1 to (ZX)-(1).60aA-514;
compounds (ZXI)-(1).60aA-1 to (ZXI)-(1).60aA-514;
compounds (ZXII)-(1).60aA-1 to (ZXII)-(1).60aA-514)
table 61a
Compounds (Z)-(1), wherein A is 2-(trifluoromethoxy)-6-fluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).61 aA-1 to (Zl)-(1 ).61 aA-514; compounds (Zll)-(1 ).61 aA-1 to (Zll)-(1 ).61 aA-514;
compounds (Zl ll)-(1 ).61 aA-1 to (ZIII)-(1).61aA-514;
compounds (ZIV)-(1).61aA-1 to (ZIV)-(1).61aA-514;
compounds (ZV)-(1).61aA-1 to (ZV)-(1).61aA-514;
compounds (ZVI)-(1).61aA-1 to (ZVI)-(1).61aA-514;
compounds (ZVII)-(1).61aA-1 to (ZVII)-(1).61aA-514;
compounds (ZVIII)-(1).61aA-1 to (ZVIII)-(1).61aA-514;
compounds (ZIX)-(1).61aA-1 to (ZIX)-(1).61aA-514;
compounds (ZX)-(1).61aA-1 to (ZX)-(1).61aA-514;
compounds (ZXI)-(1).61aA-1 to (ZXI)-(1).61aA-514;
compounds (ZXII)-(1).61aA-1 to (ZXII)-(1).61aA-514)
table 62a
Compounds (Z)-(1), wherein A is 3-(trifluoromethoxy)-4-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).62aA-1 to (Zl)-(1 ).62aA-514; compounds (ZII)-(1).62aA-1 to (ZII)-(1).62aA-514;
compounds (ZIII)-(1).62aA-1 to (ZIII)-(1).62aA-514;
compounds (ZIV)-(1).62aA-1 to (ZIV)-(1).62aA-514;
compounds (ZV)-(1 ).62aA-1 to (ZV)-(1 ).62aA-514;
compounds (ZVI)-(1).62aA-1 to (ZVI)-(1).62aA-514;
compounds (ZVII)-(1).62aA-1 to (ZVII)-(1).62aA-514;
compounds (ZVIII)-(1).62aA-1 to (ZVIII)-(1).62aA-514;
compounds (ZIX)-(1).62aA-1 to (ZIX)-(1).62aA-514;
compounds (ZX)-(1 ).62aA-1 to (ZX)-(1 ).62aA-514;
compounds (ZXI)-(1).62aA-1 to (ZXI)-(1).62aA-514;
compounds (ZXII)-(1).62aA-1 to (ZXII)-(1).62aA-514)
table 63a
Compounds (Z)-(1), wherein A is 3-(trifluoromethoxy)-5-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).63aA-1 to (Zl)-(1 ).63aA-514; compounds (ZII)-(1).63aA-1 to (ZII)-(1).63aA-514;
compounds (ZIII)-(1).63aA-1 to (ZIII)-(1).63aA-514;
compounds (ZIV)-(1).63aA-1 to (ZIV)-(1).63aA-514;
compounds (ZV)-(1).63aA-1 to (ZV)-(1).63aA-514;
compounds (ZVI)-(1).63aA-1 to (ZVI)-(1).63aA-514;
compounds (ZVII)-(1).63aA-1 to (ZVII)-(1).63aA-514;
compounds (ZVIII)-(1).63aA-1 to (ZVIII)-(1).63aA-514;
compounds (ZIX)-(1).63aA-1 to (ZIX)-(1).63aA-514;
compounds (ZX)-(1).63aA-1 to (ZX)-(1).63aA-514;
compounds (ZXI)-(1).63aA-1 to (ZXI)-(1).63aA-514;
compounds (ZXII)-(1).63aA-1 to (ZXII)-(1).63aA-514)
table 64a
Compounds (Z)-(1), wherein A is 2-fluoro-3-(trifluoromethoxy)phenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).64aA-1 to (Zl)-(1 ).64aA-514; compounds (ZII)-(1).64aA-1 to (ZII)-(1).64aA-514;
compounds (ZIII)-(1).64aA-1 to (ZIII)-(1).64aA-514;
compounds (ZIV)-(1).64aA-1 to (ZIV)-(1).64aA-514;
compounds (ZV)-(1).64aA-1 to (ZV)-(1).64aA-514;
compounds (ZVI)-(1).64aA-1 to (ZVI)-(1).64aA-514;
compounds (ZVII)-(1).64aA-1 to (ZVII)-(1).64aA-514;
compounds (ZVIII)-(1).64aA-1 to (ZVIII)-(1).64aA-514;
compounds (ZIX)-(1).64aA-1 to (ZIX)-(1).64aA-514;
compounds (ZX)-(1).64aA-1 to (ZX)-(1).64aA-514;
compounds (ZXI)-(1).64aA-1 to (ZXI)-(1).64aA-514;
compounds (ZXII)-(1).64aA-1 to (ZXII)-(1).64aA-514)
table 65a
Compounds (Z)-(1), wherein A is 2-fluoro-4-(trifluoromethoxy)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).65aA-1 to (ZI)-(1).65aA-514; compounds (ZII)-(1).65aA-1 to (ZII)-(1).65aA-514;
compounds (ZIII)-(1).65aA-1 to (ZIII)-(1).65aA-514;
compounds (ZIV)-(1).65aA-1 to (ZIV)-(1).65aA-514;
compounds (ZV)-(1 ).65aA-1 to (ZV)-(1 ).65aA-514;
compounds (ZVI)-(1).65aA-1 to (ZVI)-(1).65aA-514;
compounds (ZVII)-(1).65aA-1 to (ZVII)-(1).65aA-514;
compounds (ZVIII)-(1).65aA-1 to (ZVIII)-(1).65aA-514;
compounds (ZIX)-(1).65aA-1 to (ZIX)-(1).65aA-514;
compounds (ZX)-(1 ).65aA-1 to (ZX)-(1 ).65aA-514;
compounds (ZXI)-(1).65aA-1 to (ZXI)-(1).65aA-514;
compounds (ZXII)-(1).65aA-1 to (ZXII)-(1).65aA-514)
table 66a
Compounds (Z)-(1), wherein A is 2-fluoro-5-(trifluoromethoxy)phenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).66aA-1 to (Zl)-(1 ).66aA-514; compounds (ZII)-(1).66aA-1 to (ZII)-(1).66aA-514;
compounds (ZIII)-(1).66aA-1 to (ZIII)-(1).66aA-514;
compounds (ZIV)-(1).66aA-1 to (ZIV)-(1).66aA-514;
compounds (ZV)-(1).66aA-1 to (ZV)-(1).66aA-514;
compounds (ZVI)-(1).66aA-1 to (ZVI)-(1).66aA-514;
compounds (ZVII)-(1).66aA-1 to (ZVII)-(1).66aA-514;
compounds (ZVIII)-(1).66aA-1 to (ZVIII)-(1).66aA-514;
compounds (ZIX)-(1).66aA-1 to (ZIX)-(1).66aA-514;
compounds (ZX)-(1).66aA-1 to (ZX)-(1).66aA-514;
compounds (ZXI)-(1).66aA-1 to (ZXI)-(1).66aA-514;
compounds (ZXII)-(1).66aA-1 to (ZXII)-(1).66aA-514)
table 67a
Compounds (Z)-(1), wherein A is 3-fluoro-4-(trifluoromethoxy)phenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).67aA-1 to (Zl)-(1 ).67aA-514; compounds (ZII)-(1).67aA-1 to (ZII)-(1).67aA-514;
compounds (ZIII)-(1).67aA-1 to (ZIII)-(1).67aA-514;
compounds (ZIV)-(1).67aA-1 to (ZIV)-(1).67aA-514;
compounds (ZV)-(1).67aA-1 to (ZV)-(1).67aA-514;
compounds (ZVI)-(1).67aA-1 to (ZVI)-(1).67aA-514;
compounds (ZVII)-(1).67aA-1 to (ZVII)-(1).67aA-514;
compounds (ZVIII)-(1).67aA-1 to (ZVIII)-(1).67aA-514;
compounds (ZIX)-(1).67aA-1 to (ZIX)-(1).67aA-514;
compounds (ZX)-(1).67aA-1 to (ZX)-(1).67aA-514;
compounds (ZXI)-(1).67aA-1 to (ZXI)-(1).67aA-514;
compounds (ZXII)-(1).67aA-1 to (ZXII)-(1).67aA-514)
table 68a
Compounds (Z)-(1), wherein A is 2-(difluoromethoxy)-3-fluorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).68aA-1 to (ZI)-(1).68aA-514; compounds (ZII)-(1).68aA-1 to (ZII)-(1).68aA-514;
compounds (ZIII)-(1).68aA-1 to (ZIII)-(1).68aA-514;
compounds (ZIV)-(1).68aA-1 to (ZIV)-(1).68aA-514;
compounds (ZV)-(1 ).68aA-1 to (ZV)-(1 ).68aA-514;
compounds (ZVI)-(1).68aA-1 to (ZVI)-(1).68aA-514;
compounds (ZVII)-(1).68aA-1 to (ZVII)-(1).68aA-514;
compounds (ZVIII)-(1).68aA-1 to (ZVIII)-(1).68aA-514;
compounds (ZIX)-(1).68aA-1 to (ZIX)-(1).68aA-514;
compounds (ZX)-(1 ).68aA-1 to (ZX)-(1 ).68aA-514;
compounds (ZXI)-(1).68aA-1 to (ZXI)-(1).68aA-514;
compounds (ZXII)-(1).68aA-1 to (ZXII)-(1).68aA-514)
table 69a
Compounds (Z)-(1), wherein A is 2-(difluoromethoxy)-4-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).69aA-1 to (Zl)-(1 ).69aA-514; compounds (ZII)-(1).69aA-1 to (ZII)-(1).69aA-514;
compounds (ZIII)-(1).69aA-1 to (ZIII)-(1).69aA-514;
compounds (ZIV)-(1).69aA-1 to (ZIV)-(1).69aA-514;
compounds (ZV)-(1).69aA-1 to (ZV)-(1).69aA-514;
compounds (ZVI)-(1).69aA-1 to (ZVI)-(1).69aA-514;
compounds (ZVII)-(1).69aA-1 to (ZVII)-(1).69aA-514;
compounds (ZVIII)-(1).69aA-1 to (ZVIII)-(1).69aA-514;
compounds (ZIX)-(1).69aA-1 to (ZIX)-(1).69aA-514;
compounds (ZX)-(1).69aA-1 to (ZX)-(1).69aA-514;
compounds (ZXI)-(1).69aA-1 to (ZXI)-(1).69aA-514;
compounds (ZXII)-(1).69aA-1 to (ZXII)-(1).69aA-514)
table 70a
Compounds (Z)-(1), wherein A is 2-(difluoromethoxy)-5-fluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).70aA-1 to (Zl)-(1 ).70aA-514; compounds (ZII)-(1).70aA-1 to (ZII)-(1).70aA-514;
compounds (ZIII)-(1).70aA-1 to (ZIII)-(1).70aA-514;
compounds (ZIV)-(1).70aA-1 to (ZIV)-(1).70aA-514;
compounds (ZV)-(1).70aA-1 to (ZV)-(1).70aA-514;
compounds (ZVI)-(1).70aA-1 to (ZVI)-(1).70aA-514;
compounds (ZVII)-(1).70aA-1 to (ZVII)-(1).70aA-514;
compounds (ZVIII)-(1).70aA-1 to (ZVIII)-(1).70aA-514;
compounds (ZIX)-(1).70aA-1 to (ZIX)-(1).70aA-514;
compounds (ZX)-(1).70aA-1 to (ZX)-(1).70aA-514;
compounds (ZXI)-(1).70aA-1 to (ZXI)-(1).70aA-514;
compounds (ZXII)-(1).70aA-1 to (ZXII)-(1).70aA-514)
table 71a
Compounds (Z)-(1), wherein A is 2-(difluoromethoxy)-6-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).71 aA-1 to (Zl)-(1 ).71 aA-514; compounds (Zll)-(1 ).71 aA-1 to (Zll)-(1 ).71 aA-514;
compounds (Zll l)-(1 ).71 aA-1 to (ZIII)-(1).71aA-514;
compounds (ZIV)-(1).71aA-1 to (ZIV)-(1).71aA-514;
compounds (ZV)-(1 ).71 aA-1 to (ZV)-(1 ).71 aA-514;
compounds (ZVI)-(1).71aA-1 to (ZVI)-(1).71aA-514;
compounds (ZVII)-(1).71aA-1 to (ZVII)-(1).71aA-514;
compounds (ZVIII)-(1).71aA-1 to (ZVIII)-(1).71aA-514;
compounds (ZIX)-(1).71aA-1 to (ZIX)-(1).71aA-514;
compounds (ZX)-(1 ).71 aA-1 to (ZX)-(1 ).71 aA-514;
compounds (ZXI)-(1).71aA-1 to (ZXI)-(1).71aA-514;
compounds (ZXII)-(1).71aA-1 to (ZXII)-(1).71aA-514)
table 72a
Compounds (Z)-(1), wherein A is 3-(difluoromethoxy)-4-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).72aA-1 to (Zl)-(1 ).72aA-514; compounds (ZII)-(1).72aA-1 to (ZII)-(1).72aA-514;
compounds (ZIII)-(1).72aA-1 to (ZIII)-(1).72aA-514;
compounds (ZIV)-(1).72aA-1 to (ZIV)-(1).72aA-514;
compounds (ZV)-(1).72aA-1 to (ZV)-(1).72aA-514;
compounds (ZVI)-(1).72aA-1 to (ZVI)-(1).72aA-514;
compounds (ZVII)-(1).72aA-1 to (ZVII)-(1).72aA-514;
compounds (ZVIII)-(1).72aA-1 to (ZVIII)-(1).72aA-514;
compounds (ZIX)-(1).72aA-1 to (ZIX)-(1).72aA-514;
compounds (ZX)-(1).72aA-1 to (ZX)-(1).72aA-514;
compounds (ZXI)-(1).72aA-1 to (ZXI)-(1).72aA-514;
compounds (ZXII)-(1).72aA-1 to (ZXII)-(1).72aA-514)
table 73a
Compounds (Z)-(1), wherein A is 3-(difluoromethoxy)-5-fluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).73aA-1 to (Zl)-(1 ).73aA-514; compounds (ZII)-(1).73aA-1 to (ZII)-(1).73aA-514;
compounds (ZIII)-(1).73aA-1 to (ZIII)-(1).73aA-514;
compounds (ZIV)-(1).73aA-1 to (ZIV)-(1).73aA-514;
compounds (ZV)-(1).73aA-1 to (ZV)-(1).73aA-514;
compounds (ZVI)-(1).73aA-1 to (ZVI)-(1).73aA-514;
compounds (ZVII)-(1).73aA-1 to (ZVII)-(1).73aA-514;
compounds (ZVIII)-(1).73aA-1 to (ZVIII)-(1).73aA-514;
compounds (ZIX)-(1).73aA-1 to (ZIX)-(1).73aA-514;
compounds (ZX)-(1).73aA-1 to (ZX)-(1).73aA-514;
compounds (ZXI)-(1).73aA-1 to (ZXI)-(1).73aA-514;
compounds (ZXII)-(1).73aA-1 to (ZXII)-(1).73aA-514)
table 74a
Compounds (Z)-(1), wherein A is 2-fluoro-3-(difluoromethoxy)phenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).74aA-1 to (Zl)-(1 ).74aA-514; compounds (ZII)-(1).74aA-1 to (ZII)-(1).74aA-514;
compounds (ZIII)-(1).74aA-1 to (ZIII)-(1).74aA-514;
compounds (ZIV)-(1).74aA-1 to (ZIV)-(1).74aA-514;
compounds (ZV)-(1 ).74aA-1 to (ZV)-(1 ).74aA-514;
compounds (ZVI)-(1).74aA-1 to (ZVI)-(1).74aA-514;
compounds (ZVII)-(1).74aA-1 to (ZVII)-(1).74aA-514;
compounds (ZVIII)-(1).74aA-1 to (ZVIII)-(1).74aA-514;
compounds (ZIX)-(1).74aA-1 to (ZIX)-(1).74aA-514;
compounds (ZX)-(1 ).74aA-1 to (ZX)-(1 ).74aA-514;
compounds (ZXI)-(1).74aA-1 to (ZXI)-(1).74aA-514;
compounds (ZXII)-(1).74aA-1 to (ZXII)-(1).74aA-514)
table 75a
Compounds (Z)-(1), wherein A is 2-fluoro-4-(difluoromethoxy)phenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).75aA-1 to (Zl)-(1 ).75aA-514; compounds (ZII)-(1).75aA-1 to (ZII)-(1).75aA-514;
compounds (ZIII)-(1).75aA-1 to (ZIII)-(1).75aA-514;
compounds (ZIV)-(1).75aA-1 to (ZIV)-(1).75aA-514;
compounds (ZV)-(1).75aA-1 to (ZV)-(1).75aA-514;
compounds (ZVI)-(1).75aA-1 to (ZVI)-(1).75aA-514;
compounds (ZVII)-(1).75aA-1 to (ZVII)-(1).75aA-514;
compounds (ZVIII)-(1).75aA-1 to (ZVIII)-(1).75aA-514;
compounds (ZIX)-(1).75aA-1 to (ZIX)-(1).75aA-514;
compounds (ZX)-(1).75aA-1 to (ZX)-(1).75aA-514;
compounds (ZXI)-(1).75aA-1 to (ZXI)-(1).75aA-514;
compounds (ZXII)-(1).75aA-1 to (ZXII)-(1).75aA-514)
table 76a
Compounds (Z)-(1), wherein A is 2-fluoro-5-(difluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).76aA-1 to (ZI)-(1).76aA-514; compounds (ZII)-(1).76aA-1 to (ZII)-(1).76aA-514;
compounds (ZIII)-(1).76aA-1 to (ZIII)-(1).76aA-514;
compounds (ZIV)-(1).76aA-1 to (ZIV)-(1).76aA-514;
compounds (ZV)-(1).76aA-1 to (ZV)-(1).76aA-514;
compounds (ZVI)-(1).76aA-1 to (ZVI)-(1).76aA-514;
compounds (ZVII)-(1).76aA-1 to (ZVII)-(1).76aA-514;
compounds (ZVIII)-(1).76aA-1 to (ZVIII)-(1).76aA-514;
compounds (ZIX)-(1).76aA-1 to (ZIX)-(1).76aA-514;
compounds (ZX)-(1).76aA-1 to (ZX)-(1).76aA-514;
compounds (ZXI)-(1).76aA-1 to (ZXI)-(1).76aA-514;
compounds (ZXII)-(1).76aA-1 to (ZXII)-(1).76aA-514)
table 77a
Compounds (Z)-(1), wherein A is 3-fluoro-4-(difluoromethoxy)phenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).77aA-1 to (Zl)-(1 ).77aA-514; compounds (ZII)-(1).77aA-1 to (ZII)-(1).77aA-514;
compounds (ZIII)-(1).77aA-1 to (ZIII)-(1).77aA-514;
compounds (ZIV)-(1).77aA-1 to (ZIV)-(1).77aA-514;
compounds (ZV)-(1 ).77aA-1 to (ZV)-(1 ).77aA-514;
compounds (ZVI)-(1).77aA-1 to (ZVI)-(1).77aA-514;
compounds (ZVII)-(1).77aA-1 to (ZVII)-(1).77aA-514;
compounds (ZVIII)-(1).77aA-1 to (ZVIII)-(1).77aA-514;
compounds (ZIX)-(1).77aA-1 to (ZIX)-(1).77aA-514;
compounds (ZX)-(1 ).77aA-1 to (ZX)-(1 ).77aA-514;
compounds (ZXI)-(1).77aA-1 to (ZXI)-(1).77aA-514;
compounds (ZXII)-(1).77aA-1 to (ZXII)-(1).77aA-514)
table 78a
Compounds (Z)-(1), wherein A is 2-(trifluoromethylthio)-3-fluorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).78aA-1 to (ZI)-(1).78aA-514; compounds (ZII)-(1).78aA-1 to (ZII)-(1).78aA-514;
compounds (ZIII)-(1).78aA-1 to (ZIII)-(1).78aA-514;
compounds (ZIV)-(1).78aA-1 to (ZIV)-(1).78aA-514;
compounds (ZV)-(1).78aA-1 to (ZV)-(1).78aA-514;
compounds (ZVI)-(1).78aA-1 to (ZVI)-(1).78aA-514;
compounds (ZVII)-(1).78aA-1 to (ZVII)-(1).78aA-514;
compounds (ZVIII)-(1).78aA-1 to (ZVIII)-(1).78aA-514;
compounds (ZIX)-(1).78aA-1 to (ZIX)-(1).78aA-514;
compounds (ZX)-(1).78aA-1 to (ZX)-(1).78aA-514;
compounds (ZXI)-(1).78aA-1 to (ZXI)-(1).78aA-514;
compounds (ZXII)-(1).78aA-1 to (ZXII)-(1).78aA-514)
table 79a
Compounds (Z)-(1), wherein A is 2-(trifluoromethylthio)-4-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).79aA-1 to (ZI)-(1).79aA-514; compounds (ZII)-(1).79aA-1 to (ZII)-(1).79aA-514;
compounds (ZIII)-(1).79aA-1 to (ZIII)-(1).79aA-514;
compounds (ZIV)-(1).79aA-1 to (ZIV)-(1).79aA-514;
compounds (ZV)-(1).79aA-1 to (ZV)-(1).79aA-514;
compounds (ZVI)-(1).79aA-1 to (ZVI)-(1).79aA-514;
compounds (ZVII)-(1).79aA-1 to (ZVII)-(1).79aA-514;
compounds (ZVIII)-(1).79aA-1 to (ZVIII)-(1).79aA-514;
compounds (ZIX)-(1).79aA-1 to (ZIX)-(1).79aA-514;
compounds (ZX)-(1).79aA-1 to (ZX)-(1).79aA-514;
compounds (ZXI)-(1).79aA-1 to (ZXI)-(1).79aA-514;
compounds (ZXII)-(1).79aA-1 to (ZXII)-(1).79aA-514)
table 80a
Compounds (Z)-(1), wherein A is 2-(trifluoromethylthio)-5-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).80aA-1 to (Zl)-(1 ).80aA-514; compounds (ZII)-(1).80aA-1 to (ZII)-(1).80aA-514;
compounds (ZIII)-(1).80aA-1 to (ZIII)-(1).80aA-514;
compounds (ZIV)-(1).80aA-1 to (ZIV)-(1).80aA-514;
compounds (ZV)-(1 ).80aA-1 to (ZV)-(1 ).80aA-514;
compounds (ZVI)-(1).80aA-1 to (ZVI)-(1).80aA-514;
compounds (ZVII)-(1).80aA-1 to (ZVII)-(1).80aA-514;
compounds (ZVIII)-(1).80aA-1 to (ZVIII)-(1).80aA-514;
compounds (ZIX)-(1).80aA-1 to (ZIX)-(1).80aA-514;
compounds (ZX)-(1 ).80aA-1 to (ZX)-(1 ).80aA-514;
compounds (ZXI)-(1).80aA-1 to (ZXI)-(1).80aA-514;
compounds (ZXII)-(1).80aA-1 to (ZXII)-(1).80aA-514)
table 81a
Compounds (Z)-(1), wherein A is 2-(trifluoromethylthio)-6-fluorophenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).81 aA-1 to (Zl)-(1 ).81 aA-514; compounds (Zll)-(1 ).81 aA-1 to (Zll)-(1 ).81 aA-514;
compounds (Zl ll)-(1 ).81 aA-1 to (Zlll)-(1 ).81 aA-514;
compounds (ZIV)-(1).81aA-1 to (ZIV)-(1).81aA-514;
compounds (ZV)-(1).81aA-1 to (ZV)-(1).81aA-514;
compounds (ZVI)-(1).81aA-1 to (ZVI)-(1).81aA-514;
compounds (ZVII)-(1).81aA-1 to (ZVII)-(1).81aA-514;
compounds (ZVIII)-(1).81aA-1 to (ZVIII)-(1).81aA-514;
compounds (ZIX)-(1).81aA-1 to (ZIX)-(1).81aA-514;
compounds (ZX)-(1).81aA-1 to (ZX)-(1).81aA-514;
compounds (ZXI)-(1).81aA-1 to (ZXI)-(1).81aA-514;
compounds (ZXII)-(1).81aA-1 to (ZXII)-(1).81 aA-514)
table 82a
Compounds (Z)-(1), wherein A is 3-(trifluoromethylthio)-4-fluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).82aA-1 to (Zl)-(1 ).82aA-514; compounds (ZII)-(1).82aA-1 to (ZII)-(1).82aA-514;
compounds (ZIII)-(1).82aA-1 to (ZIII)-(1).82aA-514;
compounds (ZIV)-(1).82aA-1 to (ZIV)-(1).82aA-514;
compounds (ZV)-(1).82aA-1 to (ZV)-(1).82aA-514;
compounds (ZVI)-(1).82aA-1 to (ZVI)-(1).82aA-514;
compounds (ZVII)-(1).82aA-1 to (ZVII)-(1).82aA-514;
compounds (ZVIII)-(1).82aA-1 to (ZVIII)-(1).82aA-514;
compounds (ZIX)-(1).82aA-1 to (ZIX)-(1).82aA-514;
compounds (ZX)-(1).82aA-1 to (ZX)-(1).82aA-514;
compounds (ZXI)-(1).82aA-1 to (ZXI)-(1).82aA-514;
compounds (ZXII)-(1).82aA-1 to (ZXII)-(1).82aA-514)
table 83a
Compounds (Z)-(1), wherein A is 3-(trifluoromethylthio)-5-fluorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).83aA-1 to (ZI)-(1).83aA-514; compounds (ZII)-(1).83aA-1 to (ZII)-(1).83aA-514;
compounds (ZIII)-(1).83aA-1 to (ZIII)-(1).83aA-514;
compounds (ZIV)-(1).83aA-1 to (ZIV)-(1).83aA-514;
compounds (ZV)-(1 ).83aA-1 to (ZV)-(1 ).83aA-514;
compounds (ZVI)-(1).83aA-1 to (ZVI)-(1).83aA-514;
compounds (ZVII)-(1).83aA-1 to (ZVII)-(1).83aA-514;
compounds (ZVIII)-(1).83aA-1 to (ZVIII)-(1).83aA-514;
compounds (ZIX)-(1).83aA-1 to (ZIX)-(1).83aA-514;
compounds (ZX)-(1 ).83aA-1 to (ZX)-(1 ).83aA-514;
compounds (ZXI)-(1).83aA-1 to (ZXI)-(1).83aA-514;
compounds (ZXII)-(1).83aA-1 to (ZXII)-(1).83aA-514)
table 84a
Compounds (Z)-(1), wherein A is 2-fluoro-3-(trifluoromethylthio)phenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).84aA-1 to (Zl)-(1 ).84aA-514; compounds (ZII)-(1).84aA-1 to (ZII)-(1).84aA-514;
compounds (ZIII)-(1).84aA-1 to (ZIII)-(1).84aA-514;
compounds (ZIV)-(1).84aA-1 to (ZIV)-(1).84aA-514;
compounds (ZV)-(1).84aA-1 to (ZV)-(1).84aA-514;
compounds (ZVI)-(1).84aA-1 to (ZVI)-(1).84aA-514;
compounds (ZVII)-(1).84aA-1 to (ZVII)-(1).84aA-514;
compounds (ZVIII)-(1).84aA-1 to (ZVIII)-(1).84aA-514;
compounds (ZIX)-(1).84aA-1 to (ZIX)-(1).84aA-514;
compounds (ZX)-(1).84aA-1 to (ZX)-(1).84aA-514;
compounds (ZXI)-(1).84aA-1 to (ZXI)-(1).84aA-514;
compounds (ZXII)-(1).84aA-1 to (ZXII)-(1).84aA-514)
table 85a
Compounds (Z)-(1), wherein A is 2-fluoro-4-(trifluoromethylthio)phenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).85aA-1 to (Zl)-(1 ).85aA-514; compounds (ZII)-(1).85aA-1 to (ZII)-(1).85aA-514;
compounds (ZIII)-(1).85aA-1 to (ZIII)-(1).85aA-514;
compounds (ZIV)-(1).85aA-1 to (ZIV)-(1).85aA-514;
compounds (ZV)-(1).85aA-1 to (ZV)-(1).85aA-514;
compounds (ZVI)-(1).85aA-1 to (ZVI)-(1).85aA-514;
compounds (ZVII)-(1).85aA-1 to (ZVII)-(1).85aA-514;
compounds (ZVIII)-(1).85aA-1 to (ZVIII)-(1).85aA-514;
compounds (ZIX)-(1).85aA-1 to (ZIX)-(1).85aA-514;
compounds (ZX)-(1).85aA-1 to (ZX)-(1).85aA-514;
compounds (ZXI)-(1).85aA-1 to (ZXI)-(1).85aA-514;
compounds (ZXII)-(1).85aA-1 to (ZXII)-(1).85aA-514)
table 86a
Compounds (Z)-(1), wherein A is 2-fluoro-5-(trifluoromethylthio)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).86aA-1 to (ZI)-(1).86aA-514; compounds (ZII)-(1).86aA-1 to (ZII)-(1).86aA-514;
compounds (ZIII)-(1).86aA-1 to (ZIII)-(1).86aA-514;
compounds (ZIV)-(1).86aA-1 to (ZIV)-(1).86aA-514;
compounds (ZV)-(1 ).86aA-1 to (ZV)-(1 ).86aA-514;
compounds (ZVI)-(1).86aA-1 to (ZVI)-(1).86aA-514;
compounds (ZVII)-(1).86aA-1 to (ZVII)-(1).86aA-514;
compounds (ZVIII)-(1).86aA-1 to (ZVIII)-(1).86aA-514;
compounds (ZIX)-(1).86aA-1 to (ZIX)-(1).86aA-514;
compounds (ZX)-(1 ).86aA-1 to (ZX)-(1 ).86aA-514;
compounds (ZXI)-(1).86aA-1 to (ZXI)-(1).86aA-514;
compounds (ZXII)-(1).86aA-1 to (ZXII)-(1).86aA-514)
table 87a
Compounds (Z)-(1), wherein A is 3-fluoro-4-(trifluoromethylthio)phenyl and B corre- sponds to one row of table A (compounds (Zl)-(1 ).87aA-1 to (Zl)-(1 ).87aA-514; compounds (ZII)-(1).87aA-1 to (ZII)-(1).87aA-514;
compounds (ZIII)-(1).87aA-1 to (ZIII)-(1).87aA-514;
compounds (ZIV)-(1).87aA-1 to (ZIV)-(1).87aA-514;
compounds (ZV)-(1).87aA-1 to (ZV)-(1).87aA-514;
compounds (ZVI)-(1).87aA-1 to (ZVI)-(1).87aA-514;
compounds (ZVII)-(1).87aA-1 to (ZVII)-(1).87aA-514;
compounds (ZVIII)-(1).87aA-1 to (ZVIII)-(1).87aA-514;
compounds (ZIX)-(1).87aA-1 to (ZIX)-(1).87aA-514;
compounds (ZX)-(1).87aA-1 to (ZX)-(1).87aA-514;
compounds (ZXI)-(1).87aA-1 to (ZXI)-(1).87aA-514;
compounds (ZXII)-(1).87aA-1 to (ZXII)-(1).87aA-514)
table 88a
Compounds (Z)-(1), wherein A is 2,3,4-trifluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).88aA-1 to (ZI)-(1).88aA-514;
compounds (ZII)-(1).88aA-1 to (ZII)-(1).88aA-514;
compounds (ZIII)-(1).88aA-1 to (ZIII)-(1).88aA-514;
compounds (ZIV)-(1).88aA-1 to (ZIV)-(1).88aA-514;
compounds (ZV)-(1).88aA-1 to (ZV)-(1).88aA-514;
compounds (ZVI)-(1).88aA-1 to (ZVI)-(1).88aA-514;
compounds (ZVII)-(1).88aA-1 to (ZVII)-(1).88aA-514;
compounds (ZVIII)-(1).88aA-1 to (ZVIII)-(1).88aA-514;
compounds (ZIX)-(1).88aA-1 to (ZIX)-(1).88aA-514;
compounds (ZX)-(1).88aA-1 to (ZX)-(1).88aA-514;
compounds (ZXI)-(1).88aA-1 to (ZXI)-(1).88aA-514;
compounds (ZXII)-(1).88aA-1 to (ZXII)-(1).88aA-514)
table 89a
Compounds (Z)-(1), wherein A is 2,3,5-trifluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).89aA-1 to (ZI)-(1).89aA-514;
compounds (ZII)-(1).89aA-1 to (ZII)-(1).89aA-514;
compounds (ZIII)-(1).89aA-1 to (ZIII)-(1).89aA-514;
compounds (ZIV)-(1).89aA-1 to (ZIV)-(1).89aA-514;
compounds (ZV)-(1 ).89aA-1 to (ZV)-(1 ).89aA-514;
compounds (ZVI)-(1).89aA-1 to (ZVI)-(1).89aA-514;
compounds (ZVII)-(1).89aA-1 to (ZVII)-(1).89aA-514;
compounds (ZVIII)-(1).89aA-1 to (ZVIII)-(1).89aA-514;
compounds (ZIX)-(1).89aA-1 to (ZIX)-(1).89aA-514;
compounds (ZX)-(1 ).89aA-1 to (ZX)-(1 ).89aA-514;
compounds (ZXI)-(1).89aA-1 to (ZXI)-(1).89aA-514;
compounds (ZXII)-(1).89aA-1 to (ZXII)-(1).89aA-514)
table 90a
Compounds (Z)-(1), wherein A is 2,3,6-trifluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).90aA-1 to (ZI)-(1).90aA-514;
compounds (ZII)-(1).90aA-1 to (ZII)-(1).90aA-514;
compounds (ZIII)-(1).90aA-1 to (ZIII)-(1).90aA-514;
compounds (ZIV)-(1).90aA-1 to (ZIV)-(1).90aA-514;
compounds (ZV)-(1).90aA-1 to (ZV)-(1).90aA-514;
compounds (ZVI)-(1).90aA-1 to (ZVI)-(1).90aA-514;
compounds (ZVII)-(1).90aA-1 to (ZVII)-(1).90aA-514;
compounds (ZVIII)-(1).90aA-1 to (ZVIII)-(1).90aA-514;
compounds (ZIX)-(1).90aA-1 to (ZIX)-(1).90aA-514;
compounds (ZX)-(1).90aA-1 to (ZX)-(1).90aA-514;
compounds (ZXI)-(1).90aA-1 to (ZXI)-(1).90aA-514;
compounds (ZXII)-(1).90aA-1 to (ZXII)-(1).90aA-514)
table 91a
Compounds (Z)-(1), wherein A is 2,4,5-trifluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).91aA-1 to (ZI)-(1).91aA-514;
compounds (ZII)-(1).91aA-1 to (Zll)-(1 ).91 aA-514;
compounds (ZIII)-(1).91aA-1 to (ZIII)-(1).91aA-514;
compounds (ZIV)-(1).91aA-1 to (ZIV)-(1).91aA-514;
compounds (ZV)-(1).91aA-1 to (ZV)-(1).91aA-514;
compounds (ZVI)-(1).91aA-1 to (ZVI)-(1).91aA-514;
compounds (ZVII)-(1).91aA-1 to (ZVII)-(1).91aA-514;
compounds (ZVIII)-(1).91aA-1 to (ZVIII)-(1).91aA-514;
compounds (ZIX)-(1).91aA-1 to (ZIX)-(1).91aA-514;
compounds (ZX)-(1).91aA-1 to (ZX)-(1).91aA-514;
compounds (ZXI)-(1).91aA-1 to (ZXI)-(1).91aA-514;
compounds (ZXII)-(1).91aA-1 to (ZXII)-(1).91aA-514)
table 92a
Compounds (Z)-(1), wherein A is 2,4,6-trifluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).92aA-1 to (ZI)-(1).92aA-514;
compounds (ZII)-(1).92aA-1 to (ZII)-(1).92aA-514;
compounds (ZIII)-(1).92aA-1 to (ZIII)-(1).92aA-514;
compounds (ZIV)-(1).92aA-1 to (ZIV)-(1).92aA-514;
compounds (ZV)-(1 ).92aA-1 to (ZV)-(1 ).92aA-514;
compounds (ZVI)-(1).92aA-1 to (ZVI)-(1).92aA-514;
compounds (ZVII)-(1).92aA-1 to (ZVII)-(1).92aA-514;
compounds (ZVIII)-(1).92aA-1 to (ZVIII)-(1).92aA-514;
compounds (ZIX)-(1).92aA-1 to (ZIX)-(1).92aA-514;
compounds (ZX)-(1 ).92aA-1 to (ZX)-(1 ).92aA-514;
compounds (ZXI)-(1).92aA-1 to (ZXI)-(1).92aA-514;
compounds (ZXII)-(1).92aA-1 to (ZXII)-(1).92aA-514)
table 93a
Compounds (Z)-(1), wherein A is 3,4,5-trifluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).93aA-1 to (ZI)-(1).93aA-514;
compounds (ZII)-(1).93aA-1 to (ZII)-(1).93aA-514;
compounds (ZIII)-(1).93aA-1 to (ZIII)-(1).93aA-514;
compounds (ZIV)-(1).93aA-1 to (ZIV)-(1).93aA-514;
compounds (ZV)-(1).93aA-1 to (ZV)-(1).93aA-514;
compounds (ZVI)-(1).93aA-1 to (ZVI)-(1).93aA-514;
compounds (ZVII)-(1).93aA-1 to (ZVII)-(1).93aA-514;
compounds (ZVIII)-(1).93aA-1 to (ZVIII)-(1).93aA-514;
compounds (ZIX)-(1).93aA-1 to (ZIX)-(1).93aA-514;
compounds (ZX)-(1).93aA-1 to (ZX)-(1).93aA-514;
compounds (ZXI)-(1).93aA-1 to (ZXI)-(1).93aA-514;
compounds (ZXII)-(1).93aA-1 to (ZXII)-(1).93aA-514)
table 94a
Compounds (Z)-(1), wherein A is phenyl and B corresponds to one row of table A
(compounds (ZI)-(1).94aA-1 to (ZI)-(1).94aA-514;
compounds (ZII)-(1).94aA-1 to (ZII)-(1).94aA-514;
compounds (ZIII)-(1).94aA-1 to (ZIII)-(1).94aA-514;
compounds (ZIV)-(1).94aA-1 to (ZIV)-(1).94aA-514;
compounds (ZV)-(1).94aA-1 to (ZV)-(1).94aA-514;
compounds (ZVI)-(1).94aA-1 to (ZVI)-(1).94aA-514;
compounds (ZVII)-(1).94aA-1 to (ZVII)-(1).94aA-514;
compounds (ZVIII)-(1).94aA-1 to (ZVIII)-(1).94aA-514;
compounds (ZIX)-(1).94aA-1 to (ZIX)-(1).94aA-514;
compounds (ZX)-(1).94aA-1 to (ZX)-(1).94aA-514;
compounds (ZXI)-(1).94aA-1 to (ZXI)-(1).94aA-514;
compounds (ZXII)-(1).94aA-1 to (ZXII)-(1).94aA-514)
table 95a
Compounds (Z)-(1), wherein A is 2-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).95aA-1 to (ZI)-(1).95aA-514;
compounds (ZII)-(1).95aA-1 to (ZII)-(1).95aA-514;
compounds (ZIII)-(1).95aA-1 to (ZIII)-(1).95aA-514;
compounds (ZIV)-(1).95aA-1 to (ZIV)-(1).95aA-514;
compounds (ZV)-(1 ).95aA-1 to (ZV)-(1 ).95aA-514;
compounds (ZVI)-(1).95aA-1 to (ZVI)-(1).95aA-514;
compounds (ZVII)-(1).95aA-1 to (ZVII)-(1).95aA-514;
compounds (ZVIII)-(1).95aA-1 to (ZVIII)-(1).95aA-514;
compounds (ZIX)-(1).95aA-1 to (ZIX)-(1).95aA-514;
compounds (ZX)-(1 ).95aA-1 to (ZX)-(1 ).95aA-514;
compounds (ZXI)-(1).95aA-1 to (ZXI)-(1).95aA-514;
compounds (ZXII)-(1).95aA-1 to (ZXII)-(1).95aA-514)
table 96a
Compounds (Z)-(1), wherein A is 3-chlorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).96aA-1 to (Zl)-(1 ).96aA-514;
compounds (ZII)-(1).96aA-1 to (ZII)-(1).96aA-514;
compounds (ZIII)-(1).96aA-1 to (ZIII)-(1).96aA-514;
compounds (ZIV)-(1).96aA-1 to (ZIV)-(1).96aA-514;
compounds (ZV)-(1).96aA-1 to (ZV)-(1).96aA-514;
compounds (ZVI)-(1).96aA-1 to (ZVI)-(1).96aA-514;
compounds (ZVII)-(1).96aA-1 to (ZVII)-(1).96aA-514;
compounds (ZVIII)-(1).96aA-1 to (ZVIII)-(1).96aA-514;
compounds (ZIX)-(1).96aA-1 to (ZIX)-(1).96aA-514;
compounds (ZX)-(1).96aA-1 to (ZX)-(1).96aA-514;
compounds (ZXI)-(1).96aA-1 to (ZXI)-(1).96aA-514;
compounds (ZXII)-(1).96aA-1 to (ZXII)-(1).96aA-514)
table 97a
Compounds (Z)-(1), wherein A is 4-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).97aA-1 to (ZI)-(1).97aA-514;
compounds (ZII)-(1).97aA-1 to (ZII)-(1).97aA-514;
compounds (ZIII)-(1).97aA-1 to (ZIII)-(1).97aA-514;
compounds (ZIV)-(1).97aA-1 to (ZIV)-(1).97aA-514;
compounds (ZV)-(1).97aA-1 to (ZV)-(1).97aA-514;
compounds (ZVI)-(1).97aA-1 to (ZVI)-(1).97aA-514;
compounds (ZVII)-(1).97aA-1 to (ZVII)-(1).97aA-514;
compounds (ZVIII)-(1).97aA-1 to (ZVIII)-(1).97aA-514;
compounds (ZIX)-(1).97aA-1 to (ZIX)-(1).97aA-514;
compounds (ZX)-(1).97aA-1 to (ZX)-(1).97aA-514;
compounds (ZXI)-(1).97aA-1 to (ZXI)-(1).97aA-514;
compounds (ZXII)-(1).97aA-1 to (ZXII)-(1).97aA-514)
table 98a
Compounds (Z)-(1), wherein A is 2-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).98aA-1 to (ZI)-(1).98aA-514;
compounds (ZII)-(1).98aA-1 to (ZII)-(1).98aA-514;
compounds (ZIII)-(1).98aA-1 to (ZIII)-(1).98aA-514;
compounds (ZIV)-(1).98aA-1 to (ZIV)-(1).98aA-514;
compounds (ZV)-(1 ).98aA-1 to (ZV)-(1 ).98aA-514;
compounds (ZVI)-(1).98aA-1 to (ZVI)-(1).98aA-514;
compounds (ZVII)-(1).98aA-1 to (ZVII)-(1).98aA-514;
compounds (ZVIII)-(1).98aA-1 to (ZVIII)-(1).98aA-514;
compounds (ZIX)-(1).98aA-1 to (ZIX)-(1).98aA-514;
compounds (ZX)-(1 ).98aA-1 to (ZX)-(1 ).98aA-514;
compounds (ZXI)-(1).98aA-1 to (ZXI)-(1).98aA-514;
compounds (ZXII)-(1).98aA-1 to (ZXII)-(1).98aA-514)
table 99a
Compounds (Z)-(1), wherein A is 3-fluorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).99aA-1 to (Zl)-(1 ).99aA-514;
compounds (ZII)-(1).99aA-1 to (ZII)-(1).99aA-514;
compounds (ZIII)-(1).99aA-1 to (ZIII)-(1).99aA-514;
compounds (ZIV)-(1).99aA-1 to (ZIV)-(1).99aA-514;
compounds (ZV)-(1).99aA-1 to (ZV)-(1).99aA-514;
compounds (ZVI)-(1).99aA-1 to (ZVI)-(1).99aA-514;
compounds (ZVII)-(1).99aA-1 to (ZVII)-(1).99aA-514;
compounds (ZVIII)-(1).99aA-1 to (ZVIII)-(1).99aA-514;
compounds (ZIX)-(1).99aA-1 to (ZIX)-(1).99aA-514;
compounds (ZX)-(1).99aA-1 to (ZX)-(1).99aA-514;
compounds (ZXI)-(1).99aA-1 to (ZXI)-(1).99aA-514;
compounds (ZXII)-(1).99aA-1 to (ZXII)-(1).99aA-514)
table 100a
Compounds (Z)-(1), wherein A is 4-fluorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).100aA-1 to (ZI)-(1).100aA-514;
compounds (Zll)-(1 ).100aA-1 to (Zll)-(1 ).100aA-514;
compounds (ZIII)-(1).100aA-1 to (Zll l)-(1 ).100aA-514;
compounds (ZIV)-(1).100aA-1 to (ZIV)-(1).100aA-514;
compounds (ZV)-(1).100aA-1 to (ZV)-(1).100aA-514;
compounds (ZVI)-(1).100aA-1 to (ZVI)-(1).100aA-514;
compounds (ZVII)-(1).100aA-1 to (ZVII)-(1).100aA-514;
compounds (ZVIII)-(1).100aA-1 to (ZVIII)-(1).100aA-514;
compounds (ZIX)-(1).100aA-1 to (ZIX)-(1).100aA-514;
compounds (ZX)-(1).100aA-1 to (ZX)-(1).100aA-514;
compounds (ZXI)-(1).100aA-1 to (ZXI)-(1).100aA-514;
compounds (ZXII)-(1).100aA-1 to (ZXII)-(1).100aA-514)
table 101a
Compounds (Z)-(1), wherein A is 2-methylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).101aA-1 to (ZI)-(1).101aA-514;
compounds (Zll)-(1 ).101 aA-1 to (ZII)-(1).101aA-514;
compounds (Zll l)-(1 ).101 aA-1 to (Zlll)-(1 ).101 aA-514;
compounds (ZIV)-(1).101aA-1 to (ZIV)-(1).101aA-514;
compounds (ZV)-(1).101aA-1 to (ZV)-(1).101aA-514;
compounds (ZVI)-(1).101aA-1 to (ZVI)-(1).101aA-514;
compounds (ZVII)-(1 ).101 aA-1 to (ZVII)-(1).101aA-514;
compounds (ZVIII)-(1).101aA-1 to (ZVIII)-(1).101aA-514;
compounds (ZIX)-(1).101aA-1 to (ZIX)-(1).101aA-514;
compounds (ZX)-(1).101aA-1 to (ZX)-(1).101aA-514;
compounds (ZXI)-(1).101aA-1 to (ZXI)-(1).101aA-514;
compounds (ZXII)-(1).101aA-1 to (ZXII)-(1).101aA-514)
table 102a
Compounds (Z)-(1), wherein A is 3-methylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).102aA-1 to (ZI)-(1).102aA-514;
compounds (ZII)-(1).102aA-1 to (ZII)-(1).102aA-514;
compounds (ZIII)-(1).102aA-1 to (ZIII)-(1).102aA-514;
compounds (ZIV)-(1).102aA-1 to (ZIV)-(1).102aA-514;
compounds (ZV)-(1).102aA-1 to (ZV)-(1).102aA-514;
compounds (ZVI)-(1).102aA-1 to (ZVI)-(1).102aA-514;
compounds (ZVII)-(1).102aA-1 to (ZVII)-(1).102aA-514;
compounds (ZVIII)-(1).102aA-1 to (ZVIII)-(1).102aA-514;
compounds (ZIX)-(1).102aA-1 to (ZIX)-(1).102aA-514;
compounds (ZX)-(1).102aA-1 to (ZX)-(1).102aA-514;
compounds (ZXI)-(1).102aA-1 to (ZXI)-(1).102aA-514;
compounds (ZXII)-(1).102aA-1 to (ZXII)-(1).102aA-514)
table 103a
Compounds (Z)-(1), wherein A is 4-methylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).103aA-1 to (ZI)-(1).103aA-514;
compounds (ZII)-(1).103aA-1 to (ZII)-(1).103aA-514;
compounds (ZIII)-(1).103aA-1 to (Zll l)-(1 ).103aA-514;
compounds (ZIV)-(1).103aA-1 to (ZIV)-(1).103aA-514;
compounds (ZV)-(1).103aA-1 to (ZV)-(1).103aA-514;
compounds (ZVI)-(1).103aA-1 to (ZVI)-(1).103aA-514;
compounds (ZVII)-(1).103aA-1 to (ZVII)-(1).103aA-514;
compounds (ZVIII)-(1).103aA-1 to (ZVIII)-(1).103aA-514;
compounds (ZIX)-(1).103aA-1 to (ZIX)-(1).103aA-514;
compounds (ZX)-(1).103aA-1 to (ZX)-(1).103aA-514;
compounds (ZXI)-(1).103aA-1 to (ZXI)-(1).103aA-514;
compounds (ZXII)-(1).103aA-1 to (ZXII)-(1).103aA-514)
table 104a
Compounds (Z)-(1), wherein A is 2-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).104aA-1 to (ZI)-(1).104aA-514;
compounds (ZII)-(1).104aA-1 to (ZII)-(1).104aA-514;
compounds (ZIII)-(1).104aA-1 to (ZIII)-(1).104aA-514;
compounds (ZIV)-(1).104aA-1 to (ZIV)-(1).104aA-514;
compounds (ZV)-(1).104aA-1 to (ZV)-(1).104aA-514;
compounds (ZVI)-(1).104aA-1 to (ZVI)-(1).104aA-514;
compounds (ZVII)-(1).104aA-1 to (ZVII)-(1).104aA-514;
compounds (ZVIII)-(1).104aA-1 to (ZVIII)-(1).104aA-514;
compounds (ZIX)-(1).104aA-1 to (ZIX)-(1).104aA-514;
compounds (ZX)-(1).104aA-1 to (ZX)-(1).104aA-514;
compounds (ZXI)-(1).104aA-1 to (ZXI)-(1).104aA-514;
compounds (ZXII)-(1).104aA-1 to (ZXII)-(1).104aA-514)
table 105a
Compounds (Z)-(1), wherein A is 3-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).105aA-1 to (ZI)-(1).105aA-514;
compounds (ZII)-(1).105aA-1 to (ZII)-(1).105aA-514;
compounds (ZIII)-(1).105aA-1 to (ZIII)-(1).105aA-514;
compounds (ZIV)-(1).105aA-1 to (ZIV)-(1).105aA-514;
compounds (ZV)-(1).105aA-1 to (ZV)-(1).105aA-514;
compounds (ZVI)-(1).105aA-1 to (ZVI)-(1).105aA-514;
compounds (ZVII)-(1).105aA-1 to (ZVII)-(1).105aA-514;
compounds (ZVIII)-(1).105aA-1 to (ZVIII)-(1).105aA-514;
compounds (ZIX)-(1).105aA-1 to (ZIX)-(1).105aA-514;
compounds (ZX)-(1).105aA-1 to (ZX)-(1).105aA-514;
compounds (ZXI)-(1).105aA-1 to (ZXI)-(1).105aA-514;
compounds (ZXII)-(1).105aA-1 to (ZXII)-(1).1aA-514)
table 106a
Compounds (Z)-(1), wherein A is 4-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).106aA-1 to (ZI)-(1).106aA-514;
compounds (ZII)-(1).106aA-1 to (ZII)-(1).106aA-514;
compounds (ZIII)-(1).106aA-1 to (ZIII)-(1).106aA-514;
compounds (ZIV)-(1).106aA-1 to (ZIV)-(1).106aA-514;
compounds (ZV)-(1).106aA-1 to (ZV)-(1).106aA-514;
compounds (ZVI)-(1).106aA-1 to (ZVI)-(1).106aA-514;
compounds (ZVII)-(1).106aA-1 to (ZVII)-(1).106aA-514;
compounds (ZVIII)-(1).106aA-1 to (ZVIII)-(1).106aA-514;
compounds (ZIX)-(1).106aA-1 to (ZIX)-(1).106aA-514;
compounds (ZX)-(1).106aA-1 to (ZX)-(1).106aA-514;
compounds (ZXI)-(1).106aA-1 to (ZXI)-(1).106aA-514;
compounds (ZXII)-(1).106aA-1 to (ZXII)-(1).106aA-514)
table 107a
Compounds (Z)-(1), wherein A is 2-methoxyphenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).107aA-1 to (Zl)-(1 ).107aA-514;
compounds (ZII)-(1).107aA-1 to (ZII)-(1).107aA-514;
compounds (ZIII)-(1).107aA-1 to (ZIII)-(1).107aA-514;
compounds (ZIV)-(1).107aA-1 to (ZIV)-(1).107aA-514;
compounds (ZV)-(1).107aA-1 to (ZV)-(1).107aA-514;
compounds (ZVI)-(1).107aA-1 to (ZVI)-(1).107aA-514;
compounds (ZVII)-(1).107aA-1 to (ZVII)-(1).107aA-514;
compounds (ZVIII)-(1).107aA-1 to (ZVIII)-(1).107aA-514;
compounds (ZIX)-(1).107aA-1 to (ZIX)-(1).107aA-514;
compounds (ZX)-(1).107aA-1 to (ZX)-(1).107aA-514;
compounds (ZXI)-(1).107aA-1 to (ZXI)-(1).107aA-514;
compounds (ZXII)-(1).107aA-1 to (ZXII)-(1).107aA-514)
table 108a
Compounds (Z)-(1), wherein A is 3-methoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).108aA-1 to (ZI)-(1).108aA-514;
compounds (ZII)-(1).108aA-1 to (ZII)-(1).108aA-514;
compounds (ZIII)-(1).108aA-1 to (ZIII)-(1).108aA-514;
compounds (ZIV)-(1).108aA-1 to (ZIV)-(1).108aA-514;
compounds (ZV)-(1).108aA-1 to (ZV)-(1).108aA-514;
compounds (ZVI)-(1).108aA-1 to (ZVI)-(1).108aA-514;
compounds (ZVII)-(1).108aA-1 to (ZVII)-(1).108aA-514;
compounds (ZVIII)-(1).108aA-1 to (ZVIII)-(1).108aA-514;
compounds (ZIX)-(1).108aA-1 to (ZIX)-(1).108aA-514;
compounds (ZX)-(1).108aA-1 to (ZX)-(1).108aA-514;
compounds (ZXI)-(1).108aA-1 to (ZXI)-(1).108aA-514;
compounds (ZXII)-(1).108aA-1 to (ZXII)-(1).108aA-514)
table 109a
Compounds (Z)-(1), wherein A is 4-methoxyphenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).109aA-1 to (Zl)-(1 ).109aA-514;
compounds (ZII)-(1).109aA-1 to (ZII)-(1).109aA-514;
compounds (ZIII)-(1).109aA-1 to (ZIII)-(1).109aA-514;
compounds (ZIV)-(1).109aA-1 to (ZIV)-(1).109aA-514;
compounds (ZV)-(1).109aA-1 to (ZV)-(1).109aA-514;
compounds (ZVI)-(1).109aA-1 to (ZVI)-(1).109aA-514;
compounds (ZVII)-(1).109aA-1 to (ZVII)-(1).109aA-514;
compounds (ZVIII)-(1).109aA-1 to (ZVIII)-(1).109aA-514;
compounds (ZIX)-(1).109aA-1 to (ZIX)-(1).109aA-514;
compounds (ZX)-(1).109aA-1 to (ZX)-(1).109aA-514;
compounds (ZXI)-(1).109aA-1 to (ZXI)-(1).109aA-514;
compounds (ZXII)-(1).109aA-1 to (ZXII)-(1).109aA-514)
table 110a
Compounds (Z)-(1), wherein A is 2-trifluoromethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).110aA-1 to (ZI)-(1).110aA-514;
compounds (Zll)-(1 ).110aA-1 to (ZII)-(1).110aA-514;
compounds (Zll l)-( ).110aA-1 to (ZIII)-(1).110aA-514;
compounds (ZIV)-(1).110aA-1 to (ZIV)-(1).110aA-514;
compounds (ZV)-(1).110aA-1 to (ZV)-(1).110aA-514;
compounds (ZVI)-(1).110aA-1 to (ZVI)-(1).110aA-514;
compounds (ZVII)-(1 ).110aA-1 to (ZVII)-(1).110aA-514;
compounds (ZVIII)-(1 ).110aA-1 to (ZVIII)-(1).110aA-514;
compounds (ZIX)-(1).110aA-1 to (ZIX)-(1).110aA-514;
compounds (ZX)-(1).110aA-1 to (ZX)-(1).110aA-514;
compounds (ZXI)-(1).110aA-1 to (ZXI)-(1).110aA-514;
compounds (ZXII)-(1 ).110aA-1 to (ZXII)-(1).110aA-514)
table 111a
Compounds (Z)-(1), wherein A is 3-trifluoromethylphenyl and B corresponds to one row of table A (compounds (Zl)-(1).111 aA-1 to (Zl)-(1).111aA-514;
compounds (ZII)-(1).111aA-1 to (ZII)-(1).111aA-514;
compounds (ZIII)-(1).111aA-1 to (Zlll)-(1 ).111 aA-514;
compounds (ZIV)-(1).111aA-1 to (ZIV)-(1).111aA-514;
compounds (ZV)-(1).111aA-1 to (ZV)-(1).111 aA-514;
compounds (ZVI)-(1).111 aA-1 to (ZVI)-(1).111 aA-514;
compounds (ZVII)-(1 ).111 aA-1 to (ZVII)-(1 ).111 aA-514;
compounds (ZVIII)-(1).111aA-1 to (ZVIII)-(1).111 aA-514;
compounds (ZIX)-(1).111aA-1 to (ZIX)-(1).111 aA-514;
compounds (ZX)-(1).111aA-1 to (ZX)-(1).111aA-514;
compounds (ZXI)-(1).111aA-1 to (ZXI)-(1).111 aA-514;
compounds (ZXII)-(1).111aA-1 to (ZXII)-(1).111aA-514)
table 112a
Compounds (Z)-(1), wherein A is 4-trifluoromethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).112aA-1 to (Zl)-(1).112aA-514;
compounds (ZII)-(1).112aA-1 to (ZII)-(1).112aA-514;
compounds (ZIII)-(1).112aA-1 to (Zlll)-(1).112aA-514;
compounds (ZIV)-(1).112aA-1 to (ZIV)-(1).112aA-514;
compounds (ZV)-(1).112aA-1 to (ZV)-(1).112aA-514;
compounds (ZVI)-(1).112aA-1 to (ZVI)-(1).112aA-514;
compounds (ZVII)-(1).112aA-1 to (ZVII)-(1).112aA-514;
compounds (ZVIII)-(1).112aA-1 to (ZVIII)-(1).112aA-514;
compounds (ZIX)-(1).112aA-1 to (ZIX)-(1).112aA-514;
compounds (ZX)-(1).112aA-1 to (ZX)-(1).112aA-514;
compounds (ZXI)-(1).112aA-1 to (ZXI)-(1).112aA-514;
compounds (ZXII)-(1).112aA-1 to (ZXII)-(1).112aA-514)
table 113a
Compounds (Z)-(1), wherein A is 2-trifluoromethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).113aA-1 to (ZI)-(1).113aA-514;
compounds (ZII)-(1).113aA-1 to (ZII)-(1).113aA-514;
compounds (Zll l)-(1 ).113aA-1 to (Zlll)-(1).113aA-514;
compounds (ZIV)-(1).113aA-1 to (ZIV)-(1).113aA-514;
compounds (ZV)-(1).113aA-1 to (ZV)-(1).113aA-514;
compounds (ZVI)-(1).113aA-1 to (ZVI)-(1).113aA-514;
compounds (ZVII)-(1).113aA-1 to (ZVII)-(1).113aA-514;
compounds (ZVIII)-(1).113aA-1 to (ZVIII)-(1).113aA-514;
compounds (ZIX)-(1).113aA-1 to (ZIX)-(1).113aA-514;
compounds (ZX)-(1).113aA-1 to (ZX)-(1).113aA-514;
compounds (ZXI)-(1).113aA-1 to (ZXI)-(1).113aA-514;
compounds (ZXII)-(1).113aA-1 to (ZXII)-(1).113aA-514)
table 114a
Compounds (Z)-(1), wherein A is 3-trifluoromethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).114aA-1 to (ZI)-(1).114aA-514;
compounds (ZII)-(1).114aA-1 to (ZII)-(1).114aA-514;
compounds (Zlll)-(1).114aA-1 to (Zlll)-(1).114aA-514;
compounds (ZIV)-(1).114aA-1 to (ZIV)-(1).114aA-514;
compounds (ZV)-(1).114aA-1 to (ZV)-(1).114aA-514;
compounds (ZVI)-(1).114aA-1 to (ZVI)-(1).114aA-514;
compounds (ZVII)-(1).114aA-1 to (ZVII)-(1).114aA-514;
compounds (ZVIII)-(1).114aA-1 to (ZVIII)-(1).114aA-514;
compounds (ZIX)-(1).114aA-1 to (ZIX)-(1).114aA-514;
compounds (ZX)-(1).114aA-1 to (ZX)-(1).114aA-514;
compounds (ZXI)-(1).114aA-1 to (ZXI)-(1).114aA-514;
compounds (ZXII)-(1).114aA-1 to (ZXII)-(1).114aA-514)
table 115a
Compounds (Z)-(1), wherein A is 4-trifluoromethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).115aA-1 to (ZI)-(1).115aA-514;
compounds (ZII)-(1).115aA-1 to (ZII)-(1).115aA-514;
compounds (ZIII)-(1).115aA-1 to (Zll l)-(1 ).115aA-514;
compounds (ZIV)-(1).115aA-1 to (ZIV)-(1).115aA-514;
compounds (ZV)-(1).115aA-1 to (ZV)-(1).115aA-514;
compounds (ZVI)-(1).115aA-1 to (ZVI)-(1).115aA-514;
compounds (ZVII)-(1 ).115aA-1 to (ZVII)-(1).115aA-514;
compounds (ZVIII)-(1).115aA-1 to (ZVIII)-(1).115aA-514;
compounds (ZIX)-(1).115aA-1 to (ZIX)-(1).115aA-514;
compounds (ZX)-(1).115aA-1 to (ZX)-(1).115aA-514;
compounds (ZXI)-(1).115aA-1 to (ZXI)-(1).115aA-514;
compounds (ZXII)-(1).115aA-1 to (ZXII)-(1).115aA-514)
table 116a
Compounds (Z)-(1), wherein A is 2-difluoromethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).116aA-1 to (ZI)-(1).116aA-514;
compounds (ZII)-(1).116aA-1 to (ZII)-(1).116aA-514;
compounds (Zll l)-(1 ).116aA-1 to (Zlll)-(1).116aA-514;
compounds (ZIV)-(1).116aA-1 to (ZIV)-(1).116aA-514;
compounds (ZV)-(1).116aA-1 to (ZV)-(1).116aA-514;
compounds (ZVI)-(1).116aA-1 to (ZVI)-(1).116aA-514;
compounds (ZVII)-(1).116aA-1 to (ZVII)-(1).116aA-514;
compounds (ZVIII)-(1).116aA-1 to (ZVIII)-(1).116aA-514;
compounds (ZIX)-(1).116aA-1 to (ZIX)-(1).116aA-514;
compounds (ZX)-(1).116aA-1 to (ZX)-(1).116aA-514;
compounds (ZXI)-(1).116aA-1 to (ZXI)-(1).116aA-514;
compounds (ZXII)-(1).116aA-1 to (ZXII)-(1).116aA-514)
table 117a
Compounds (Z)-(1), wherein A is 3-difluoromethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).117aA-1 to (ZI)-(1).117aA-514;
compounds (ZII)-(1).117aA-1 to (ZII)-(1).117aA-514;
compounds (Zlll)-(1).117aA-1 to (Zll l)-(1 ).117aA-514;
compounds (ZIV)-(1).117aA-1 to (ZIV)-(1).117aA-514;
compounds (ZV)-(1).117aA-1 to (ZV)-(1).117aA-514;
compounds (ZVI)-(1).117aA-1 to (ZVI)-(1).117aA-514;
compounds (ZVII)-(1).117aA-1 to (ZVII)-(1).117aA-514;
compounds (ZVIII)-(1).117aA-1 to (ZVIII)-(1).117aA-514;
compounds (ZIX)-(1).117aA-1 to (ZIX)-(1).117aA-514;
compounds (ZX)-(1).117aA-1 to (ZX)-(1).117aA-514;
compounds (ZXI)-(1).117aA-1 to (ZXI)-(1).117aA-514;
compounds (ZXII)-(1).117aA-1 to (ZXII)-(1).117aA-514)
table 118a
Compounds (Z)-(1), wherein A is 4-difluoromethoxyphenyl and B corresponds to one row of table A (compounds (Zl)-(1).118aA-1 to (ZI)-(1).118aA-514;
compounds (ZII)-(1).118aA-1 to (Zll)-(1).118aA-514;
compounds (ZIII)-(1).118aA-1 to (Zlll)-(1).118aA-514;
compounds (ZIV)-(1).118aA-1 to (ZIV)-(1).118aA-514;
compounds (ZV)-(1).118aA-1 to (ZV)-(1).118aA-514;
compounds (ZVI)-(1).118aA-1 to (ZVI)-(1).118aA-514;
compounds (ZVII)-(1 ).118aA-1 to (ZVII)-(1).118aA-514;
compounds (ZVIII)-(1).118aA-1 to (ZVIII)-(1).118aA-514;
compounds (ZIX)-(1).118aA-1 to (ZIX)-(1).118aA-514;
compounds (ZX)-(1).118aA-1 to (ZX)-(1).118aA-514;
compounds (ZXI)-(1).118aA-1 to (ZXI)-(1).118aA-514;
compounds (ZXII)-(1).118aA-1 to (ZXII)-(1).118aA-514)
table 119a
Compounds (Z)-(1), wherein A is 2-trifluoromethylthiophenyl and B corresponds to one row of table A (compounds (ZI)-(1).119aA-1 to (ZI)-(1).119aA-514;
compounds (ZII)-(1).119aA-1 to (ZII)-(1).119aA-514;
compounds (ZIII)-(1).119aA-1 to (Zlll)-(1).119aA-514;
compounds (ZIV)-(1).119aA-1 to (ZIV)-(1).119aA-514;
compounds (ZV)-(1).119aA-1 to (ZV)-(1).119aA-514;
compounds (ZVI)-(1).119aA-1 to (ZVI)-(1).119aA-514;
compounds (ZVII)-(1).119aA-1 to (ZVII)-(1).119aA-514;
compounds (ZVIII)-(1).119aA-1 to (ZVIII)-(1).119aA-514;
compounds (ZIX)-(1).119aA-1 to (ZIX)-(1).119aA-514;
compounds (ZX)-(1).119aA-1 to (ZX)-(1).119aA-514;
compounds (ZXI)-(1).119aA-1 to (ZXI)-(1).119aA-514;
compounds (ZXII)-(1).119aA-1 to (ZXII)-(1).119aA-514)
table 120a
Compounds (Z)-(1), wherein A is 3-trifluoromethylthiophenyl and B corresponds to one row of table A (compounds (ZI)-(1).120aA-1 to (ZI)-(1).120aA-514;
compounds (ZII)-(1).120aA-1 to (ZII)-(1).120aA-514;
compounds (ZIII)-(1).120aA-1 to (ZIII)-(1).120aA-514;
compounds (ZIV)-(1).120aA-1 to (ZIV)-(1).120aA-514;
compounds (ZV)-(1).120aA-1 to (ZV)-(1).120aA-514;
compounds (ZVI)-(1).120aA-1 to (ZVI)-(1).120aA-514;
compounds (ZVII)-(1).120aA-1 to (ZVII)-(1).120aA-514;
compounds (ZVIII)-(1).120aA-1 to (ZVIII)-(1).120aA-514;
compounds (ZIX)-(1).120aA-1 to (ZIX)-(1).120aA-514;
compounds (ZX)-(1).120aA-1 to (ZX)-(1).120aA-514;
compounds (ZXI)-(1).120aA-1 to (ZXI)-(1).120aA-514;
compounds (ZXII)-(1).120aA-1 to (ZXII)-(1).120aA-514)
table 121a
Compounds (Z)-(1), wherein A is 4-trifluoromethylthiophenyl and B corresponds to one row of table A (compounds (ZI)-(1).121aA-1 to (ZI)-(1).121aA-514;
compounds (Zll)-(1 ).121 aA-1 to (ZII)-(1).121aA-514;
compounds (ZIII)-(1).121aA-1 to (Zll l)-(1 ).121 aA-514;
compounds (ZIV)-(1).121aA-1 to (ZIV)-(1).121aA-514;
compounds (ZV)-(1).121aA-1 to (ZV)-(1).121aA-514;
compounds (ZVI)-(1).121aA-1 to (ZVI)-(1).121aA-514;
compounds (ZVII)-(1 ).121 aA-1 to (ZVII)-(1).121aA-514;
compounds (ZVIII)-(1).121aA-1 to (ZVIII)-(1).121aA-514;
compounds (ZIX)-(1).121aA-1 to (ZIX)-(1).121aA-514;
compounds (ZX)-(1).121aA-1 to (ZX)-(1).121aA-514;
compounds (ZXI)-(1).121aA-1 to (ZXI)-(1).121aA-514;
compounds (ZXII)-(1).121aA-1 to (ZXII)-(1).121aA-514)
table 122a
Compounds (Z)-(1), wherein A is 2,3-dichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).122aA-1 to (ZI)-(1).122aA-514;
compounds (ZII)-(1).122aA-1 to (ZII)-(1).122aA-514;
compounds (ZIII)-(1).122aA-1 to (ZIII)-(1).122aA-514;
compounds (ZIV)-(1).122aA-1 to (ZIV)-(1).122aA-514;
compounds (ZV)-(1).122aA-1 to (ZV)-(1).122aA-514;
compounds (ZVI)-(1).122aA-1 to (ZVI)-(1).122aA-514;
compounds (ZVII)-(1).122aA-1 to (ZVII)-(1).122aA-514;
compounds (ZVIII)-(1).122aA-1 to (ZVIII)-(1).122aA-514;
compounds (ZIX)-(1).122aA-1 to (ZIX)-(1).122aA-514;
compounds (ZX)-(1).122aA-1 to (ZX)-(1).122aA-514;
compounds (ZXI)-(1).122aA-1 to (ZXI)-(1).122aA-514;
compounds (ZXII)-(1).122aA-1 to (ZXII)-(1).122aA-514)
table 123a
Compounds (Z)-(1), wherein A is 2,4-dichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).123aA-1 to (ZI)-(1).123aA-514;
compounds (ZII)-(1).123aA-1 to (ZII)-(1).123aA-514;
compounds (ZIII)-(1).123aA-1 to (ZIII)-(1).123aA-514;
compounds (ZIV)-(1).123aA-1 to (ZIV)-(1).123aA-514;
compounds (ZV)-(1).123aA-1 to (ZV)-(1).123aA-514;
compounds (ZVI)-(1).123aA-1 to (ZVI)-(1).123aA-514;
compounds (ZVII)-(1).123aA-1 to (ZVII)-(1).123aA-514;
compounds (ZVIII)-(1).123aA-1 to (ZVIII)-(1).123aA-514;
compounds (ZIX)-(1).123aA-1 to (ZIX)-(1).123aA-514;
compounds (ZX)-(1).123aA-1 to (ZX)-(1).123aA-514;
compounds (ZXI)-(1).123aA-1 to (ZXI)-(1).123aA-514;
compounds (ZXII)-(1).123aA-1 to (ZXII)-(1).123aA-514)
table 124a
Compounds (Z)-(1), wherein A is 2,5-dichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).124aA-1 to (ZI)-(1).124aA-514;
compounds (ZII)-(1).124aA-1 to (ZII)-(1).124aA-514;
compounds (ZIII)-(1).124aA-1 to (ZIII)-(1).124aA-514;
compounds (ZIV)-(1).124aA-1 to (ZIV)-(1).124aA-514;
compounds (ZV)-(1).124aA-1 to (ZV)-(1).124aA-514;
compounds (ZVI)-(1).124aA-1 to (ZVI)-(1).124aA-514;
compounds (ZVII)-(1).124aA-1 to (ZVII)-(1).124aA-514;
compounds (ZVIII)-(1).124aA-1 to (ZVIII)-(1).124aA-514;
compounds (ZIX)-(1).124aA-1 to (ZIX)-(1).124aA-514;
compounds (ZX)-(1).124aA-1 to (ZX)-(1).124aA-514;
compounds (ZXI)-(1).124aA-1 to (ZXI)-(1).124aA-514;
compounds (ZXII)-(1).124aA-1 to (ZXII)-(1).124aA-514)
table 125a
Compounds (Z)-(1), wherein A is 2,6-dichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).125aA-1 to (ZI)-(1).125aA-514;
compounds (ZII)-(1).125aA-1 to (ZII)-(1).125aA-514;
compounds (ZIII)-(1).125aA-1 to (ZIII)-(1).125aA-514;
compounds (ZIV)-(1).125aA-1 to (ZIV)-(1).125aA-514;
compounds (ZV)-(1).125aA-1 to (ZV)-(1).125aA-514;
compounds (ZVI)-(1).125aA-1 to (ZVI)-(1).125aA-514;
compounds (ZVII)-(1).125aA-1 to (ZVII)-(1).125aA-514;
compounds (ZVIII)-(1).125aA-1 to (ZVIII)-(1).125aA-514;
compounds (ZIX)-(1).125aA-1 to (ZIX)-(1).125aA-514;
compounds (ZX)-(1).125aA-1 to (ZX)-(1).125aA-514;
compounds (ZXI)-(1).125aA-1 to (ZXI)-(1).125aA-514;
compounds (ZXII)-(1).125aA-1 to (ZXII)-(1).125aA-514)
table 126a
Compounds (Z)-(1), wherein A is 3,4-dichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).126aA-1 to (ZI)-(1).126aA-514;
compounds (ZII)-(1).126aA-1 to (ZII)-(1).126aA-514;
compounds (ZIII)-(1).126aA-1 to (ZIII)-(1).126aA-514;
compounds (ZIV)-(1).126aA-1 to (ZIV)-(1).126aA-514;
compounds (ZV)-(1).126aA-1 to (ZV)-(1).126aA-514;
compounds (ZVI)-(1).126aA-1 to (ZVI)-(1).126aA-514;
compounds (ZVII)-(1).126aA-1 to (ZVII)-(1).126aA-514;
compounds (ZVIII)-(1).126aA-1 to (ZVIII)-(1).126aA-514;
compounds (ZIX)-(1).126aA-1 to (ZIX)-(1).126aA-514;
compounds (ZX)-(1).126aA-1 to (ZX)-(1).126aA-514;
compounds (ZXI)-(1).126aA-1 to (ZXI)-(1).126aA-514;
compounds (ZXII)-(1).126aA-1 to (ZXII)-(1).126aA-514)
table 127a
Compounds (Z)-(1), wherein A is 3,5-dichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).127aA-1 to (ZI)-(1).127aA-514;
compounds (ZII)-(1).127aA-1 to (ZII)-(1).127aA-514;
compounds (ZIII)-(1).127aA-1 to (ZIII)-(1).127aA-514;
compounds (ZIV)-(1).127aA-1 to (ZIV)-(1).127aA-514;
compounds (ZV)-(1).127aA-1 to (ZV)-(1).127aA-514;
compounds (ZVI)-(1).127aA-1 to (ZVI)-(1).127aA-514;
compounds (ZVII)-(1).127aA-1 to (ZVII)-(1).127aA-514;
compounds (ZVIII)-(1).127aA-1 to (ZVIII)-(1).127aA-514;
compounds (ZIX)-(1).127aA-1 to (ZIX)-(1).127aA-514;
compounds (ZX)-(1).127aA-1 to (ZX)-(1).127aA-514;
compounds (ZXI)-(1).127aA-1 to (ZXI)-(1).127aA-514;
compounds (ZXII)-(1).127aA-1 to (ZXII)-(1).127aA-514)
table 128a
Compounds (Z)-(1), wherein A is 2,3-dimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).128aA-1 to (ZI)-(1).128aA-514;
compounds (ZII)-(1).128aA-1 to (ZII)-(1).128aA-514;
compounds (ZIII)-(1).128aA-1 to (ZIII)-(1).128aA-514;
compounds (ZIV)-(1).128aA-1 to (ZIV)-(1).128aA-514;
compounds (ZV)-(1).128aA-1 to (ZV)-(1).128aA-514;
compounds (ZVI)-(1).128aA-1 to (ZVI)-(1).128aA-514;
compounds (ZVII)-(1).128aA-1 to (ZVII)-(1).128aA-514;
compounds (ZVIII)-(1).128aA-1 to (ZVIII)-(1).128aA-514;
compounds (ZIX)-(1).128aA-1 to (ZIX)-(1).128aA-514;
compounds (ZX)-(1).128aA-1 to (ZX)-(1).128aA-514;
compounds (ZXI)-(1).128aA-1 to (ZXI)-(1).128aA-514;
compounds (ZXII)-(1).128aA-1 to (ZXII)-(1).128aA-514)
table 129a
Compounds (Z)-(1), wherein A is 2,4-dimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).129aA-1 to (ZI)-(1).129aA-514;
compounds (ZII)-(1).129aA-1 to (ZII)-(1).129aA-514;
compounds (ZIII)-(1).129aA-1 to (ZIII)-(1).129aA-514;
compounds (ZIV)-(1).129aA-1 to (ZIV)-(1).129aA-514;
compounds (ZV)-(1).129aA-1 to (ZV)-(1).129aA-514;
compounds (ZVI)-(1).129aA-1 to (ZVI)-(1).129aA-514;
compounds (ZVII)-(1).129aA-1 to (ZVII)-(1).129aA-514;
compounds (ZVIII)-(1).129aA-1 to (ZVIII)-(1).129aA-514;
compounds (ZIX)-(1).129aA-1 to (ZIX)-(1).129aA-514;
compounds (ZX)-(1).129aA-1 to (ZX)-(1).129aA-514;
compounds (ZXI)-(1).129aA-1 to (ZXI)-(1).129aA-514;
compounds (ZXII)-(1).129aA-1 to (ZXII)-(1).129aA-514)
table 130a
Compounds (Z)-(1), wherein A is 2,5-dimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).130aA-1 to (ZI)-(1).130aA-514;
compounds (ZII)-(1).130aA-1 to (ZII)-(1).130aA-514;
compounds (ZIII)-(1).130aA-1 to (ZIII)-(1).130aA-514;
compounds (ZIV)-(1).130aA-1 to (ZIV)-(1).130aA-514;
compounds (ZV)-(1).130aA-1 to (ZV)-(1).130aA-514;
compounds (ZVI)-(1).130aA-1 to (ZVI)-(1).130aA-514;
compounds (ZVII)-(1).130aA-1 to (ZVII)-(1).130aA-514;
compounds (ZVIII)-(1).130aA-1 to (ZVIII)-(1).130aA-514;
compounds (ZIX)-(1).130aA-1 to (ZIX)-(1).130aA-514;
compounds (ZX)-(1).130aA-1 to (ZX)-(1).130aA-514;
compounds (ZXI)-(1).130aA-1 to (ZXI)-(1).130aA-514;
compounds (ZXII)-(1).130aA-1 to (ZXII)-(1).130aA-514)
table 131a
Compounds (Z)-(1), wherein A is 2,6-dimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).131aA-1 to (ZI)-(1).131aA-514;
compounds (ZII)-(1).131aA-1 to (ZII)-(1).131aA-514;
compounds (ZIII)-(1).131aA-1 to (Zlll)-(1 ).131 aA-514;
compounds (ZIV)-(1).131aA-1 to (ZIV)-(1).131aA-514;
compounds (ZV)-(1).131aA-1 to (ZV)-(1).131aA-514;
compounds (ZVI)-(1).131aA-1 to (ZVI)-(1).131aA-514;
compounds (ZVII)-(1 ).131 aA-1 to (ZVII)-(1).131aA-514;
compounds (ZVIII)-(1).131aA-1 to (ZVIII)-(1).131aA-514;
compounds (ZIX)-(1).131aA-1 to (ZIX)-(1).131aA-514;
compounds (ZX)-(1).131aA-1 to (ZX)-(1).131aA-514;
compounds (ZXI)-(1).131aA-1 to (ZXI)-(1).131aA-514;
compounds (ZXII)-(1).131aA-1 to (ZXII)-(1).131aA-514)
table 132a
Compounds (Z)-(1), wherein A is 3,4-dimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).132aA-1 to (ZI)-(1).132aA-514;
compounds (ZII)-(1).132aA-1 to (ZII)-(1).132aA-514;
compounds (ZIII)-(1).132aA-1 to (ZIII)-(1).132aA-514;
compounds (ZIV)-(1).132aA-1 to (ZIV)-(1).132aA-514;
compounds (ZV)-(1).132aA-1 to (ZV)-(1).132aA-514;
compounds (ZVI)-(1).132aA-1 to (ZVI)-(1).132aA-514;
compounds (ZVII)-(1).132aA-1 to (ZVII)-(1).132aA-514;
compounds (ZVIII)-(1).132aA-1 to (ZVIII)-(1).132aA-514;
compounds (ZIX)-(1).132aA-1 to (ZIX)-(1).132aA-514;
compounds (ZX)-(1).132aA-1 to (ZX)-(1).132aA-514;
compounds (ZXI)-(1).132aA-1 to (ZXI)-(1).132aA-514;
compounds (ZXII)-(1).132aA-1 to (ZXII)-(1).132aA-514)
table 133a
Compounds (Z)-(1), wherein A is 3,5-dimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).133aA-1 to (ZI)-(1).133aA-514;
compounds (ZII)-(1).133aA-1 to (ZII)-(1).133aA-514;
compounds (ZIII)-(1).133aA-1 to (ZIII)-(1).133aA-514;
compounds (ZIV)-(1).133aA-1 to (ZIV)-(1).133aA-514;
compounds (ZV)-(1).133aA-1 to (ZV)-(1).133aA-514;
compounds (ZVI)-(1).133aA-1 to (ZVI)-(1).133aA-514;
compounds (ZVII)-(1).133aA-1 to (ZVII)-(1).133aA-514;
compounds (ZVIII)-(1).133aA-1 to (ZVIII)-(1).133aA-514;
compounds (ZIX)-(1).133aA-1 to (ZIX)-(1).133aA-514;
compounds (ZX)-(1).133aA-1 to (ZX)-(1).133aA-514;
compounds (ZXI)-(1).133aA-1 to (ZXI)-(1).133aA-514;
compounds (ZXII)-(1).133aA-1 to (ZXII)-(1).133aA-514)
table 134a
Compounds (Z)-(1), wherein A is 2,3-diethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).134aA-1 to (ZI)-(1).134aA-514;
compounds (ZII)-(1).134aA-1 to (ZII)-(1).134aA-514;
compounds (ZIII)-(1).134aA-1 to (ZIII)-(1).134aA-514;
compounds (ZIV)-(1).134aA-1 to (ZIV)-(1).134aA-514;
compounds (ZV)-(1).134aA-1 to (ZV)-(1).134aA-514;
compounds (ZVI)-(1).134aA-1 to (ZVI)-(1).134aA-514;
compounds (ZVII)-(1).134aA-1 to (ZVII)-(1).134aA-514;
compounds (ZVIII)-(1).134aA-1 to (ZVIII)-(1).134aA-514;
compounds (ZIX)-(1).134aA-1 to (ZIX)-(1).134aA-514;
compounds (ZX)-(1).134aA-1 to (ZX)-(1).134aA-514;
compounds (ZXI)-(1).134aA-1 to (ZXI)-(1).134aA-514;
compounds (ZXII)-(1).134aA-1 to (ZXII)-(1).134aA-514)
table 135a
Compounds (Z)-(1), wherein A is 2,4-diethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).135aA-1 to (ZI)-(1).135aA-514;
compounds (ZII)-(1).135aA-1 to (ZII)-(1).135aA-514;
compounds (ZIII)-(1).135aA-1 to (ZIII)-(1).135aA-514;
compounds (ZIV)-(1).135aA-1 to (ZIV)-(1).135aA-514;
compounds (ZV)-(1).135aA-1 to (ZV)-(1).135aA-514;
compounds (ZVI)-(1).135aA-1 to (ZVI)-(1).135aA-514;
compounds (ZVII)-(1).135aA-1 to (ZVII)-(1).135aA-514;
compounds (ZVIII)-(1).135aA-1 to (ZVIII)-(1).135aA-514;
compounds (ZIX)-(1).135aA-1 to (ZIX)-(1).135aA-514;
compounds (ZX)-(1).135aA-1 to (ZX)-(1).135aA-514;
compounds (ZXI)-(1).135aA-1 to (ZXI)-(1).135aA-514;
compounds (ZXII)-(1).135aA-1 to (ZXII)-(1).135aA-514)
table 136a
Compounds (Z)-(1), wherein A is 2,5-diethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).136aA-1 to (ZI)-(1).136aA-514;
compounds (ZII)-(1).136aA-1 to (ZII)-(1).136aA-514;
compounds (ZIII)-(1).136aA-1 to (ZIII)-(1).136aA-514;
compounds (ZIV)-(1).136aA-1 to (ZIV)-(1).136aA-514;
compounds (ZV)-(1).136aA-1 to (ZV)-(1).136aA-514;
compounds (ZVI)-(1).136aA-1 to (ZVI)-(1).136aA-514;
compounds (ZVII)-(1).136aA-1 to (ZVII)-(1).136aA-514;
compounds (ZVIII)-(1).136aA-1 to (ZVIII)-(1).136aA-514;
compounds (ZIX)-(1).136aA-1 to (ZIX)-(1).136aA-514;
compounds (ZX)-(1).136aA-1 to (ZX)-(1).136aA-514;
compounds (ZXI)-(1).136aA-1 to (ZXI)-(1).136aA-514;
compounds (ZXII)-(1).136aA-1 to (ZXII)-(1).136aA-514)
table 137a
Compounds (Z)-(1), wherein A is 2,6-diethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).137aA-1 to (ZI)-(1).137aA-514;
compounds (ZII)-(1).137aA-1 to (ZII)-(1).137aA-514;
compounds (ZIII)-(1).137aA-1 to (ZIII)-(1).137aA-514;
compounds (ZIV)-(1).137aA-1 to (ZIV)-(1).137aA-514;
compounds (ZV)-(1).137aA-1 to (ZV)-(1).137aA-514;
compounds (ZVI)-(1).137aA-1 to (ZVI)-(1).137aA-514;
compounds (ZVII)-(1).137aA-1 to (ZVII)-(1).137aA-514;
compounds (ZVIII)-(1).137aA-1 to (ZVIII)-(1).137aA-514;
compounds (ZIX)-(1).137aA-1 to (ZIX)-(1).137aA-514;
compounds (ZX)-(1).137aA-1 to (ZX)-(1).137aA-514;
compounds (ZXI)-(1).137aA-1 to (ZXI)-(1).137aA-514;
compounds (ZXII)-(1).137aA-1 to (ZXII)-(1).137aA-514)
table 138a
Compounds (Z)-(1), wherein A is 3,4-diethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).138aA-1 to (ZI)-(1).138aA-514;
compounds (ZII)-(1).138aA-1 to (ZII)-(1).138aA-514;
compounds (ZIII)-(1).138aA-1 to (ZIII)-(1).138aA-514;
compounds (ZIV)-(1).138aA-1 to (ZIV)-(1).138aA-514;
compounds (ZV)-(1).138aA-1 to (ZV)-(1).138aA-514;
compounds (ZVI)-(1).138aA-1 to (ZVI)-(1).138aA-514;
compounds (ZVII)-(1).138aA-1 to (ZVII)-(1).138aA-514;
compounds (ZVIII)-(1).138aA-1 to (ZVIII)-(1).138aA-514;
compounds (ZIX)-(1).138aA-1 to (ZIX)-(1).138aA-514;
compounds (ZX)-(1).138aA-1 to (ZX)-(1).138aA-514;
compounds (ZXI)-(1).138aA-1 to (ZXI)-(1).138aA-514;
compounds (ZXII)-(1).138aA-1 to (ZXII)-(1).138aA-514)
table 139a
Compounds (Z)-(1), wherein A is 3,5-diethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).139aA-1 to (ZI)-(1).139aA-514;
compounds (ZII)-(1).139aA-1 to (ZII)-(1).139aA-514;
compounds (ZIII)-(1).139aA-1 to (ZIII)-(1).139aA-514;
compounds (ZIV)-(1).139aA-1 to (ZIV)-(1).139aA-514;
compounds (ZV)-(1).139aA-1 to (ZV)-(1).139aA-514;
compounds (ZVI)-(1).139aA-1 to (ZVI)-(1).139aA-514;
compounds (ZVII)-(1).139aA-1 to (ZVII)-(1).139aA-514;
compounds (ZVIII)-(1).139aA-1 to (ZVIII)-(1).139aA-514;
compounds (ZIX)-(1).139aA-1 to (ZIX)-(1).139aA-514;
compounds (ZX)-(1).139aA-1 to (ZX)-(1).139aA-514;
compounds (ZXI)-(1).139aA-1 to (ZXI)-(1).139aA-514;
compounds (ZXII)-(1).139aA-1 to (ZXII)-(1).139aA-514)
table 140a
Compounds (Z)-(1), wherein A is 2,3-dimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).140aA-1 to (ZI)-(1).140aA-514;
compounds (ZII)-(1).140aA-1 to (ZII)-(1).140aA-514;
compounds (ZIII)-(1).140aA-1 to (ZIII)-(1).140aA-514;
compounds (ZIV)-(1).140aA-1 to (ZIV)-(1).140aA-514;
compounds (ZV)-(1).140aA-1 to (ZV)-(1).140aA-514;
compounds (ZVI)-(1).140aA-1 to (ZVI)-(1).140aA-514;
compounds (ZVII)-(1).140aA-1 to (ZVII)-(1).140aA-514;
compounds (ZVIII)-(1).140aA-1 to (ZVIII)-(1).140aA-514;
compounds (ZIX)-(1).140aA-1 to (ZIX)-(1).140aA-514;
compounds (ZX)-(1).140aA-1 to (ZX)-(1).140aA-514;
compounds (ZXI)-(1).140aA-1 to (ZXI)-(1).140aA-514;
compounds (ZXII)-(1).140aA-1 to (ZXII)-(1).140aA-514)
table 141a
Compounds (Z)-(1), wherein A is 2,4-dimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).141aA-1 to (ZI)-(1).141aA-514;
compounds (ZII)-(1).141aA-1 to (ZII)-(1).141aA-514;
compounds (ZIII)-(1).141aA-1 to (Zll l)-(1 ).141 aA-514;
compounds (ZIV)-(1).141aA-1 to (ZIV)-(1).141aA-514;
compounds (ZV)-(1).141aA-1 to (ZV)-(1).141aA-514;
compounds (ZVI)-(1).141aA-1 to (ZVI)-(1).141aA-514;
compounds (ZVII)-(1).141aA-1 to (ZVII)-(1).141aA-514;
compounds (ZVIII)-(1).141aA-1 to (ZVIII)-(1 ).141 aA-514;
compounds (ZIX)-(1).141aA-1 to (ZIX)-(1).141aA-514;
compounds (ZX)-(1).141aA-1 to (ZX)-(1).141aA-514;
compounds (ZXI)-(1).141aA-1 to (ZXI)-(1).141aA-514;
compounds (ZXII)-(1).141aA-1 to (ZXII)-(1).141aA-514)
table 142a
Compounds (Z)-(1), wherein A is 2,5-dimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).142aA-1 to (ZI)-(1).142aA-514;
compounds (ZII)-(1).142aA-1 to (ZII)-(1).142aA-514;
compounds (ZIII)-(1).142aA-1 to (ZIII)-(1).142aA-514;
compounds (ZIV)-(1).142aA-1 to (ZIV)-(1).142aA-514;
compounds (ZV)-(1).142aA-1 to (ZV)-(1).142aA-514;
compounds (ZVI)-(1).142aA-1 to (ZVI)-(1).142aA-514;
compounds (ZVII)-(1).142aA-1 to (ZVII)-(1).142aA-514;
compounds (ZVIII)-(1).142aA-1 to (ZVIII)-(1).142aA-514;
compounds (ZIX)-(1).142aA-1 to (ZIX)-(1).142aA-514;
compounds (ZX)-(1).142aA-1 to (ZX)-(1).142aA-514;
compounds (ZXI)-(1).142aA-1 to (ZXI)-(1).142aA-514;
compounds (ZXII)-(1).142aA-1 to (ZXII)-(1).142aA-514)
table 143a
Compounds (Z)-(1), wherein A is 2,6-dimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).143aA-1 to (ZI)-(1).143aA-514;
compounds (ZII)-(1).143aA-1 to (ZII)-(1).143aA-514;
compounds (ZIII)-(1).143aA-1 to (ZIII)-(1).143aA-514;
compounds (ZIV)-(1).143aA-1 to (ZIV)-(1).143aA-514;
compounds (ZV)-(1).143aA-1 to (ZV)-(1).143aA-514;
compounds (ZVI)-(1).143aA-1 to (ZVI)-(1).143aA-514;
compounds (ZVII)-(1).143aA-1 to (ZVII)-(1).143aA-514;
compounds (ZVIII)-(1).143aA-1 to (ZVIII)-(1).143aA-514;
compounds (ZIX)-(1).143aA-1 to (ZIX)-(1).143aA-514;
compounds (ZX)-(1).143aA-1 to (ZX)-(1).143aA-514;
compounds (ZXI)-(1).143aA-1 to (ZXI)-(1).143aA-514;
compounds (ZXII)-(1).143aA-1 to (ZXII)-(1).143aA-514)
table 144a
Compounds (Z)-(1), wherein A is 3,4-dimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).144aA-1 to (ZI)-(1).144aA-514;
compounds (ZII)-(1).144aA-1 to (ZII)-(1).144aA-514;
compounds (ZIII)-(1).144aA-1 to (ZIII)-(1).144aA-514;
compounds (ZIV)-(1).144aA-1 to (ZIV)-(1).144aA-514;
compounds (ZV)-(1).144aA-1 to (ZV)-(1).144aA-514;
compounds (ZVI)-(1).144aA-1 to (ZVI)-(1).144aA-514;
compounds (ZVII)-(1).144aA-1 to (ZVII)-(1).144aA-514;
compounds (ZVIII)-(1).144aA-1 to (ZVIII)-(1).144aA-514;
compounds (ZIX)-(1).144aA-1 to (ZIX)-(1).144aA-514;
compounds (ZX)-(1).144aA-1 to (ZX)-(1).144aA-514;
compounds (ZXI)-(1).144aA-1 to (ZXI)-(1).144aA-514;
compounds (ZXII)-(1).144aA-1 to (ZXII)-(1).144aA-514)
table 145a
Compounds (Z)-(1), wherein A is 3,5-dimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).145aA-1 to (ZI)-(1).145aA-514;
compounds (ZII)-(1).145aA-1 to (ZII)-(1).145aA-514;
compounds (ZIII)-(1).145aA-1 to (ZIII)-(1).145aA-514;
compounds (ZIV)-(1).145aA-1 to (ZIV)-(1).145aA-514;
compounds (ZV)-(1).145aA-1 to (ZV)-(1).145aA-514;
compounds (ZVI)-(1).145aA-1 to (ZVI)-(1).145aA-514;
compounds (ZVII)-(1).145aA-1 to (ZVII)-(1).145aA-514;
compounds (ZVIII)-(1).145aA-1 to (ZVIII)-(1).145aA-514;
compounds (ZIX)-(1).145aA-1 to (ZIX)-(1).145aA-514;
compounds (ZX)-(1).145aA-1 to (ZX)-(1).145aA-514;
compounds (ZXI)-(1).145aA-1 to (ZXI)-(1).145aA-514;
compounds (ZXII)-(1).145aA-1 to (ZXII)-(1).145aA-514)
table 146a
Compounds (Z)-(1), wherein A is 2,3-di(trifluoromethyl)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).146aA-1 to (ZI)-(1).146aA-514;
compounds (ZII)-(1).146aA-1 to (ZII)-(1).146aA-514;
compounds (ZIII)-(1).146aA-1 to (ZIII)-(1).146aA-514;
compounds (ZIV)-(1).146aA-1 to (ZIV)-(1).146aA-514;
compounds (ZV)-(1).146aA-1 to (ZV)-(1).146aA-514;
compounds (ZVI)-(1).146aA-1 to (ZVI)-(1).146aA-514;
compounds (ZVII)-(1).146aA-1 to (ZVII)-(1).146aA-514;
compounds (ZVIII)-(1).146aA-1 to (ZVIII)-(1).146aA-514;
compounds (ZIX)-(1).146aA-1 to (ZIX)-(1).146aA-514;
compounds (ZX)-(1).146aA-1 to (ZX)-(1).146aA-514;
compounds (ZXI)-(1).146aA-1 to (ZXI)-(1).146aA-514;
compounds (ZXII)-(1).146aA-1 to (ZXII)-(1).146aA-514)
table 147a
Compounds (Z)-(1), wherein A is 2,4-di(trifluoromethyl)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).147aA-1 to (ZI)-(1).147aA-514;
compounds (ZII)-(1).147aA-1 to (ZII)-(1).147aA-514;
compounds (ZIII)-(1).147aA-1 to (ZIII)-(1).147aA-514;
compounds (ZIV)-(1).147aA-1 to (ZIV)-(1).147aA-514;
compounds (ZV)-(1).147aA-1 to (ZV)-(1).147aA-514;
compounds (ZVI)-(1).147aA-1 to (ZVI)-(1).147aA-514;
compounds (ZVII)-(1).147aA-1 to (ZVII)-(1).147aA-514;
compounds (ZVIII)-(1).147aA-1 to (ZVIII)-(1).147aA-514;
compounds (ZIX)-(1).147aA-1 to (ZIX)-(1).147aA-514;
compounds (ZX)-(1).147aA-1 to (ZX)-(1).147aA-514;
compounds (ZXI)-(1).147aA-1 to (ZXI)-(1).147aA-514;
compounds (ZXII)-(1).147aA-1 to (ZXII)-(1).147aA-514)
table 148a
Compounds (Z)-(1), wherein A is 2,5-di(trifluoromethyl)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).148aA-1 to (ZI)-(1).148aA-514;
compounds (ZII)-(1).148aA-1 to (ZII)-(1).148aA-514;
compounds (ZIII)-(1).148aA-1 to (ZIII)-(1).148aA-514;
compounds (ZIV)-(1).148aA-1 to (ZIV)-(1).148aA-514;
compounds (ZV)-(1).148aA-1 to (ZV)-(1).148aA-514;
compounds (ZVI)-(1).148aA-1 to (ZVI)-(1).148aA-514;
compounds (ZVII)-(1).148aA-1 to (ZVII)-(1).148aA-514;
compounds (ZVIII)-(1).148aA-1 to (ZVIII)-(1).148aA-514;
compounds (ZIX)-(1).148aA-1 to (ZIX)-(1).148aA-514;
compounds (ZX)-(1).148aA-1 to (ZX)-(1).148aA-514;
compounds (ZXI)-(1).148aA-1 to (ZXI)-(1).148aA-514;
compounds (ZXII)-(1).148aA-1 to (ZXII)-(1).148aA-514)
table 149a
Compounds (Z)-(1), wherein A is 2,6-di(trifluoromethyl)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).149aA-1 to (ZI)-(1).149aA-514;
compounds (ZII)-(1).149aA-1 to (ZII)-(1).149aA-514;
compounds (ZIII)-(1).149aA-1 to (ZIII)-(1).149aA-514;
compounds (ZIV)-(1).149aA-1 to (ZIV)-(1).149aA-514;
compounds (ZV)-(1).149aA-1 to (ZV)-(1).149aA-514;
compounds (ZVI)-(1).149aA-1 to (ZVI)-(1).149aA-514;
compounds (ZVII)-(1).149aA-1 to (ZVII)-(1).149aA-514;
compounds (ZVIII)-(1).149aA-1 to (ZVIII)-(1).149aA-514;
compounds (ZIX)-(1).149aA-1 to (ZIX)-(1).149aA-514;
compounds (ZX)-(1).149aA-1 to (ZX)-(1).149aA-514;
compounds (ZXI)-(1).149aA-1 to (ZXI)-(1).149aA-514;
compounds (ZXII)-(1).149aA-1 to (ZXII)-(1).149aA-514)
table 150a
Compounds (Z)-(1), wherein A is 3,4-di(trifluoromethyl)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).150aA-1 to (ZI)-(1).150aA-514;
compounds (ZII)-(1).150aA-1 to (ZII)-(1).150aA-514;
compounds (ZIII)-(1).150aA-1 to (ZIII)-(1).150aA-514;
compounds (ZIV)-(1).150aA-1 to (ZIV)-(1).150aA-514;
compounds (ZV)-(1).150aA-1 to (ZV)-(1).150aA-514;
compounds (ZVI)-(1).150aA-1 to (ZVI)-(1).150aA-514;
compounds (ZVII)-(1).150aA-1 to (ZVII)-(1).150aA-514;
compounds (ZVIII)-(1).150aA-1 to (ZVIII)-(1).150aA-514;
compounds (ZIX)-(1).150aA-1 to (ZIX)-(1).150aA-514;
compounds (ZX)-(1).150aA-1 to (ZX)-(1).150aA-514;
compounds (ZXI)-(1).150aA-1 to (ZXI)-(1).150aA-514;
compounds (ZXII)-(1).150aA-1 to (ZXII)-(1).150aA-514)
table 151a
Compounds (Z)-(1), wherein A is 3,5-di(trifluoromethyl)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).151aA-1 to (ZI)-(1).151aA-514;
compounds (Zll)-(1 ).151 aA-1 to (ZII)-(1).151aA-514;
compounds (Zl ll)-(1 ).151 aA-1 to (Zll l)-(1 ).151 aA-514;
compounds (ZIV)-(1).151 aA-1 to (ZIV)-(1).151aA-514;
compounds (ZV)-(1).151 aA-1 to (ZV)-(1).151aA-514;
compounds (ZVI)-(1).151aA-1 to (ZVI)-(1).151aA-514;
compounds (ZVII)-(1).151aA-1 to (ZVII)-(1).151aA-514;
compounds (ZVIII)-(1).151aA-1 to (ZVIII)-(1).151aA-514;
compounds (ZIX)-(1).151aA-1 to (ZIX)-(1).151aA-514;
compounds (ZX)-(1).151 aA-1 to (ZX)-(1).151aA-514;
compounds (ZXI)-(1).151 aA-1 to (ZXI)-(1).151aA-514;
compounds (ZXII)-(1).151 aA-1 to (ZXII)-(1).151aA-514)
table 152a
Compounds (Z)-(1), wherein A is 2,3-di(trifluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).152aA-1 to (ZI)-(1).152aA-514;
compounds (ZII)-(1).152aA-1 to (ZII)-(1).152aA-514;
compounds (ZIII)-(1).152aA-1 to (ZIII)-(1).152aA-514;
compounds (ZIV)-(1).152aA-1 to (ZIV)-(1).152aA-514;
compounds (ZV)-(1).152aA-1 to (ZV)-(1).152aA-514;
compounds (ZVI)-(1).152aA-1 to (ZVI)-(1).152aA-514;
compounds (ZVII)-(1).152aA-1 to (ZVII)-(1).152aA-514;
compounds (ZVIII)-(1).152aA-1 to (ZVIII)-(1).152aA-514;
compounds (ZIX)-(1).152aA-1 to (ZIX)-(1).152aA-514;
compounds (ZX)-(1).152aA-1 to (ZX)-(1).152aA-514;
compounds (ZXI)-(1).152aA-1 to (ZXI)-(1).152aA-514;
compounds (ZXII)-(1).152aA-1 to (ZXII)-(1).152aA-514)
table 153a
Compounds (Z)-(1), wherein A is 2,4-di(trifluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).153aA-1 to (ZI)-(1).153aA-514;
compounds (ZII)-(1).153aA-1 to (ZII)-(1).153aA-514;
compounds (ZIII)-(1).153aA-1 to (ZIII)-(1).153aA-514;
compounds (ZIV)-(1).153aA-1 to (ZIV)-(1).153aA-514;
compounds (ZV)-(1).153aA-1 to (ZV)-(1).153aA-514;
compounds (ZVI)-(1).153aA-1 to (ZVI)-(1).153aA-514;
compounds (ZVII)-(1).153aA-1 to (ZVII)-(1).153aA-514;
compounds (ZVIII)-(1).153aA-1 to (ZVIII)-(1).153aA-514;
compounds (ZIX)-(1).153aA-1 to (ZIX)-(1).153aA-514;
compounds (ZX)-(1).153aA-1 to (ZX)-(1).153aA-514;
compounds (ZXI)-(1).153aA-1 to (ZXI)-(1).153aA-514;
compounds (ZXII)-(1).153aA-1 to (ZXII)-(1).153aA-514)
table 154a
Compounds (Z)-(1), wherein A is 2,5-di(trifluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).154aA-1 to (ZI)-(1).154aA-514;
compounds (ZII)-(1).154aA-1 to (ZII)-(1).154aA-514;
compounds (ZIII)-(1).154aA-1 to (ZIII)-(1).154aA-514;
compounds (ZIV)-(1).154aA-1 to (ZIV)-(1).154aA-514;
compounds (ZV)-(1).154aA-1 to (ZV)-(1).154aA-514;
compounds (ZVI)-(1).154aA-1 to (ZVI)-(1).154aA-514;
compounds (ZVII)-(1).154aA-1 to (ZVII)-(1).154aA-514;
compounds (ZVIII)-(1).154aA-1 to (ZVIII)-(1).154aA-514;
compounds (ZIX)-(1).154aA-1 to (ZIX)-(1).154aA-514;
compounds (ZX)-(1).154aA-1 to (ZX)-(1).154aA-514;
compounds (ZXI)-(1).154aA-1 to (ZXI)-(1).154aA-514;
compounds (ZXII)-(1).154aA-1 to (ZXII)-(1).154aA-514)
table 155a
Compounds (Z)-(1), wherein A is 2,6-di(trifluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).155aA-1 to (ZI)-(1).155aA-514;
compounds (ZII)-(1).155aA-1 to (ZII)-(1).155aA-514;
compounds (ZIII)-(1).155aA-1 to (ZIII)-(1).155aA-514;
compounds (ZIV)-(1).155aA-1 to (ZIV)-(1).155aA-514;
compounds (ZV)-(1).155aA-1 to (ZV)-(1).155aA-514;
compounds (ZVI)-(1).155aA-1 to (ZVI)-(1).155aA-514;
compounds (ZVII)-(1).155aA-1 to (ZVII)-(1).155aA-514;
compounds (ZVIII)-(1).155aA-1 to (ZVIII)-(1).155aA-514;
compounds (ZIX)-(1).155aA-1 to (ZIX)-(1).155aA-514;
compounds (ZX)-(1).155aA-1 to (ZX)-(1).155aA-514;
compounds (ZXI)-(1).155aA-1 to (ZXI)-(1).155aA-514;
compounds (ZXII)-(1).155aA-1 to (ZXII)-(1).155aA-514)
table 156a
Compounds (Z)-(1), wherein A is 3,4-di(trifluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).156aA-1 to (ZI)-(1).156aA-514;
compounds (ZII)-(1).156aA-1 to (ZII)-(1).156aA-514;
compounds (ZIII)-(1).156aA-1 to (ZIII)-(1).156aA-514;
compounds (ZIV)-(1).156aA-1 to (ZIV)-(1).156aA-514;
compounds (ZV)-(1).156aA-1 to (ZV)-(1).156aA-514;
compounds (ZVI)-(1).156aA-1 to (ZVI)-(1).156aA-514;
compounds (ZVII)-(1).156aA-1 to (ZVII)-(1).156aA-514;
compounds (ZVIII)-(1).156aA-1 to (ZVIII)-(1).156aA-514;
compounds (ZIX)-(1).156aA-1 to (ZIX)-(1).156aA-514;
compounds (ZX)-(1).156aA-1 to (ZX)-(1).156aA-514;
compounds (ZXI)-(1).156aA-1 to (ZXI)-(1).156aA-514;
compounds (ZXII)-(1).156aA-1 to (ZXII)-(1).156aA-514)
table 157a
Compounds (Z)-(1), wherein A is 3,5-di(trifluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).157aA-1 to (ZI)-(1).157aA-514;
compounds (ZII)-(1).157aA-1 to (ZII)-(1).157aA-514;
compounds (ZIII)-(1).157aA-1 to (ZIII)-(1).157aA-514;
compounds (ZIV)-(1).157aA-1 to (ZIV)-(1).157aA-514;
compounds (ZV)-(1).157aA-1 to (ZV)-(1).157aA-514;
compounds (ZVI)-(1).157aA-1 to (ZVI)-(1).157aA-514;
compounds (ZVII)-(1).157aA-1 to (ZVII)-(1).157aA-514;
compounds (ZVIII)-(1).157aA-1 to (ZVIII)-(1).157aA-514;
compounds (ZIX)-(1).157aA-1 to (ZIX)-(1).157aA-514;
compounds (ZX)-(1).157aA-1 to (ZX)-(1).157aA-514;
compounds (ZXI)-(1).157aA-1 to (ZXI)-(1).157aA-514;
compounds (ZXII)-(1).157aA-1 to (ZXII)-(1).157aA-514)
table 158a
Compounds (Z)-(1), wherein A is 2,3-di(difluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).158aA-1 to (ZI)-(1).158aA-514;
compounds (ZII)-(1).158aA-1 to (ZII)-(1).158aA-514;
compounds (ZIII)-(1).158aA-1 to (ZIII)-(1).158aA-514;
compounds (ZIV)-(1).158aA-1 to (ZIV)-(1).158aA-514;
compounds (ZV)-(1).158aA-1 to (ZV)-(1).158aA-514;
compounds (ZVI)-(1).158aA-1 to (ZVI)-(1).158aA-514;
compounds (ZVII)-(1).158aA-1 to (ZVII)-(1).158aA-514;
compounds (ZVIII)-(1).158aA-1 to (ZVIII)-(1).158aA-514;
compounds (ZIX)-(1).158aA-1 to (ZIX)-(1).158aA-514;
compounds (ZX)-(1).158aA-1 to (ZX)-(1).158aA-514;
compounds (ZXI)-(1).158aA-1 to (ZXI)-(1).158aA-514;
compounds (ZXII)-(1).158aA-1 to (ZXII)-(1).158aA-514)
table 159a
Compounds (Z)-(1), wherein A is 2,4-di(difluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).159aA-1 to (ZI)-(1).159aA-514;
compounds (ZII)-(1).159aA-1 to (ZII)-(1).159aA-514;
compounds (ZIII)-(1).159aA-1 to (ZIII)-(1).159aA-514;
compounds (ZIV)-(1).159aA-1 to (ZIV)-(1).159aA-514;
compounds (ZV)-(1).159aA-1 to (ZV)-(1).159aA-514;
compounds (ZVI)-(1).159aA-1 to (ZVI)-(1).159aA-514;
compounds (ZVII)-(1).159aA-1 to (ZVII)-(1).159aA-514;
compounds (ZVIII)-(1).159aA-1 to (ZVIII)-(1).159aA-514;
compounds (ZIX)-(1).159aA-1 to (ZIX)-(1).159aA-514;
compounds (ZX)-(1).159aA-1 to (ZX)-(1).159aA-514;
compounds (ZXI)-(1).159aA-1 to (ZXI)-(1).159aA-514;
compounds (ZXII)-(1).159aA-1 to (ZXII)-(1).159aA-514)
table 160a
Compounds (Z)-(1), wherein A is 2,5-di(difluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).160aA-1 to (ZI)-(1).160aA-514;
compounds (ZII)-(1).160aA-1 to (ZII)-(1).160aA-514;
compounds (ZIII)-(1).160aA-1 to (ZIII)-(1).160aA-514;
compounds (ZIV)-(1).160aA-1 to (ZIV)-(1).160aA-514;
compounds (ZV)-(1).160aA-1 to (ZV)-(1).160aA-514;
compounds (ZVI)-(1).160aA-1 to (ZVI)-(1).160aA-514;
compounds (ZVII)-(1).160aA-1 to (ZVII)-(1).160aA-514;
compounds (ZVIII)-(1).160aA-1 to (ZVIII)-(1).160aA-514;
compounds (ZIX)-(1).160aA-1 to (ZIX)-(1).160aA-514;
compounds (ZX)-(1).160aA-1 to (ZX)-(1).160aA-514;
compounds (ZXI)-(1).160aA-1 to (ZXI)-(1).160aA-514;
compounds (ZXII)-(1).160aA-1 to (ZXII)-(1).160aA-514)
table 161a
Compounds (Z)-(1), wherein A is 2,6-di(difluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).161aA-1 to (ZI)-(1).161aA-514;
compounds (ZII)-(1).161aA-1 to (ZII)-(1).161aA-514;
compounds (ZIII)-(1).161aA-1 to (Zlll)-(1 ).161 aA-514;
compounds (ZIV)-(1).161aA-1 to (ZIV)-(1).161aA-514;
compounds (ZV)-(1).161aA-1 to (ZV)-(1).161aA-514;
compounds (ZVI)-(1).161aA-1 to (ZVI)-(1).161aA-514;
compounds (ZVII)-(1 ).161 aA-1 to (ZVII)-(1).161aA-514;
compounds (ZVIII)-(1).161aA-1 to (ZVIII)-(1).161aA-514;
compounds (ZIX)-(1).161aA-1 to (ZIX)-(1).161aA-514;
compounds (ZX)-(1).161 aA-1 to (ZX)-(1).161aA-514;
compounds (ZXI)-(1).161 aA-1 to (ZXI)-(1).161aA-514;
compounds (ZXII)-(1).161 aA-1 to (ZXII)-(1).161aA-514)
table 162a
Compounds (Z)-(1), wherein A is 3,4-di(difluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).162aA-1 to (ZI)-(1).162aA-514;
compounds (ZII)-(1).162aA-1 to (ZII)-(1).162aA-514;
compounds (ZIII)-(1).162aA-1 to (ZIII)-(1).162aA-514;
compounds (ZIV)-(1).162aA-1 to (ZIV)-(1).162aA-514;
compounds (ZV)-(1).162aA-1 to (ZV)-(1).162aA-514;
compounds (ZVI)-(1).162aA-1 to (ZVI)-(1).162aA-514;
compounds (ZVII)-(1).162aA-1 to (ZVII)-(1).162aA-514;
compounds (ZVIII)-(1).162aA-1 to (ZVIII)-(1).162aA-514;
compounds (ZIX)-(1).162aA-1 to (ZIX)-(1).162aA-514;
compounds (ZX)-(1).162aA-1 to (ZX)-(1).162aA-514;
compounds (ZXI)-(1).162aA-1 to (ZXI)-(1).162aA-514;
compounds (ZXII)-(1).162aA-1 to (ZXII)-(1).162aA-514)
table 163a
Compounds (Z)-(1), wherein A is 3,5-di(difluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).163aA-1 to (ZI)-(1).163aA-514;
compounds (ZII)-(1).163aA-1 to (ZII)-(1).163aA-514;
compounds (ZIII)-(1).163aA-1 to (ZIII)-(1).163aA-514;
compounds (ZIV)-(1).163aA-1 to (ZIV)-(1).163aA-514;
compounds (ZV)-(1).163aA-1 to (ZV)-(1).163aA-514;
compounds (ZVI)-(1).163aA-1 to (ZVI)-(1).163aA-514;
compounds (ZVII)-(1).163aA-1 to (ZVII)-(1).163aA-514;
compounds (ZVIII)-(1).163aA-1 to (ZVIII)-(1).163aA-514;
compounds (ZIX)-(1).163aA-1 to (ZIX)-(1).163aA-514;
compounds (ZX)-(1).163aA-1 to (ZX)-(1).163aA-514;
compounds (ZXI)-(1).163aA-1 to (ZXI)-(1).163aA-514;
compounds (ZXII)-(1).163aA-1 to (ZXII)-(1).163aA-514)
table 164a
Compounds (Z)-(1), wherein A is 2,3-di(trifluoromethylthio)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).164aA-1 to (ZI)-(1).164aA-514; compounds (ZII)-(1).164aA-1 to (ZII)-(1).164aA-514;
compounds (ZIII)-(1).164aA-1 to (ZIII)-(1).164aA-514;
compounds (ZIV)-(1).164aA-1 to (ZIV)-(1).164aA-514;
compounds (ZV)-(1).164aA-1 to (ZV)-(1).164aA-514;
compounds (ZVI)-(1).164aA-1 to (ZVI)-(1).164aA-514;
compounds (ZVII)-(1).164aA-1 to (ZVII)-(1).164aA-514;
compounds (ZVIII)-(1).164aA-1 to (ZVIII)-(1).164aA-514;
compounds (ZIX)-(1).164aA-1 to (ZIX)-(1).164aA-514;
compounds (ZX)-(1).164aA-1 to (ZX)-(1).164aA-514;
compounds (ZXI)-(1).164aA-1 to (ZXI)-(1).164aA-514;
compounds (ZXII)-(1).164aA-1 to (ZXII)-(1).164aA-514)
table 165a
Compounds (Z)-(1), wherein A is 2,4-di(trifluoromethylthio)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).165aA-1 to (ZI)-(1).165aA-514; compounds (ZII)-(1).165aA-1 to (ZII)-(1).165aA-514;
compounds (ZIII)-(1).165aA-1 to (ZIII)-(1).165aA-514;
compounds (ZIV)-(1).165aA-1 to (ZIV)-(1).165aA-514;
compounds (ZV)-(1).165aA-1 to (ZV)-(1).165aA-514;
compounds (ZVI)-(1).165aA-1 to (ZVI)-(1).165aA-514;
compounds (ZVII)-(1).165aA-1 to (ZVII)-(1).165aA-514;
compounds (ZVIII)-(1).165aA-1 to (ZVIII)-(1).165aA-514;
compounds (ZIX)-(1).165aA-1 to (ZIX)-(1).165aA-514;
compounds (ZX)-(1).165aA-1 to (ZX)-(1).165aA-514;
compounds (ZXI)-(1).165aA-1 to (ZXI)-(1).165aA-514;
compounds (ZXII)-(1).165aA-1 to (ZXII)-(1).165aA-514)
table 166a
Compounds (Z)-(1), wherein A is 2,5-di(trifluoromethylthio)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).166aA-1 to (ZI)-(1).166aA-514; compounds (ZII)-(1).166aA-1 to (ZII)-(1).166aA-514;
compounds (ZIII)-(1).166aA-1 to (ZIII)-(1).166aA-514;
compounds (ZIV)-(1).166aA-1 to (ZIV)-(1).166aA-514;
compounds (ZV)-(1).166aA-1 to (ZV)-(1).166aA-514;
compounds (ZVI)-(1).166aA-1 to (ZVI)-(1).166aA-514;
compounds (ZVII)-(1).166aA-1 to (ZVII)-(1).166aA-514;
compounds (ZVIII)-(1).166aA-1 to (ZVIII)-(1).166aA-514;
compounds (ZIX)-(1).166aA-1 to (ZIX)-(1).166aA-514;
compounds (ZX)-(1).166aA-1 to (ZX)-(1).166aA-514;
compounds (ZXI)-(1).166aA-1 to (ZXI)-(1).166aA-514;
compounds (ZXII)-(1).166aA-1 to (ZXII)-(1).166aA-514)
table 167a
Compounds (Z)-(1), wherein A is 2,6-di(trifluoromethylthio)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).167aA-1 to (ZI)-(1).167aA-514; compounds (ZII)-(1).167aA-1 to (ZII)-(1).167aA-514;
compounds (ZIII)-(1).167aA-1 to (ZIII)-(1).167aA-514;
compounds (ZIV)-(1).167aA-1 to (ZIV)-(1).167aA-514;
compounds (ZV)-(1).167aA-1 to (ZV)-(1).167aA-514;
compounds (ZVI)-(1).167aA-1 to (ZVI)-(1).167aA-514;
compounds (ZVII)-(1).167aA-1 to (ZVII)-(1).167aA-514;
compounds (ZVIII)-(1).167aA-1 to (ZVIII)-(1).167aA-514;
compounds (ZIX)-(1).167aA-1 to (ZIX)-(1).167aA-514;
compounds (ZX)-(1).167aA-1 to (ZX)-(1).167aA-514;
compounds (ZXI)-(1).167aA-1 to (ZXI)-(1).167aA-514;
compounds (ZXII)-(1).167aA-1 to (ZXII)-(1).167aA-514)
table 168a
Compounds (Z)-(1), wherein A is 3,4-di(trifluoromethylthio)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).168aA-1 to (ZI)-(1).168aA-514; compounds (ZII)-(1).168aA-1 to (ZII)-(1).168aA-514;
compounds (ZIII)-(1).168aA-1 to (ZIII)-(1).168aA-514;
compounds (ZIV)-(1).168aA-1 to (ZIV)-(1).168aA-514;
compounds (ZV)-(1).168aA-1 to (ZV)-(1).168aA-514;
compounds (ZVI)-(1).168aA-1 to (ZVI)-(1).168aA-514;
compounds (ZVII)-(1).168aA-1 to (ZVII)-(1).168aA-514;
compounds (ZVIII)-(1).168aA-1 to (ZVIII)-(1).168aA-514;
compounds (ZIX)-(1).168aA-1 to (ZIX)-(1).168aA-514;
compounds (ZX)-(1).168aA-1 to (ZX)-(1).168aA-514;
compounds (ZXI)-(1).168aA-1 to (ZXI)-(1).168aA-514;
compounds (ZXII)-(1).168aA-1 to (ZXII)-(1).168aA-514)
table 169a
Compounds (Z)-(1), wherein A is 3,5-di(trifluoromethylthio)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).169aA-1 to (ZI)-(1).169aA-514; compounds (ZII)-(1).169aA-1 to (ZII)-(1).169aA-514;
compounds (ZIII)-(1).169aA-1 to (ZIII)-(1).169aA-514;
compounds (ZIV)-(1).169aA-1 to (ZIV)-(1).169aA-514;
compounds (ZV)-(1).169aA-1 to (ZV)-(1).169aA-514;
compounds (ZVI)-(1).169aA-1 to (ZVI)-(1).169aA-514;
compounds (ZVII)-(1).169aA-1 to (ZVII)-(1).169aA-514;
compounds (ZVIII)-(1).169aA-1 to (ZVIII)-(1).169aA-514;
compounds (ZIX)-(1).169aA-1 to (ZIX)-(1).169aA-514;
compounds (ZX)-(1).169aA-1 to (ZX)-(1).169aA-514;
compounds (ZXI)-(1).169aA-1 to (ZXI)-(1).169aA-514;
compounds (ZXII)-(1).169aA-1 to (ZXII)-(1).169aA-514)
table 170a
Compounds (Z)-(1), wherein A is 2-methyl-3-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).170aA-1 to (ZI)-(1).170aA-514;
compounds (ZII)-(1).170aA-1 to (ZII)-(1).170aA-514;
compounds (ZIII)-(1).170aA-1 to (ZIII)-(1).170aA-514;
compounds (ZIV)-(1).170aA-1 to (ZIV)-(1).170aA-514;
compounds (ZV)-(1).170aA-1 to (ZV)-(1).170aA-514;
compounds (ZVI)-(1).170aA-1 to (ZVI)-(1).170aA-514;
compounds (ZVII)-(1).170aA-1 to (ZVII)-(1).170aA-514;
compounds (ZVIII)-(1).170aA-1 to (ZVIII)-(1).170aA-514;
compounds (ZIX)-(1).170aA-1 to (ZIX)-(1).170aA-514;
compounds (ZX)-(1).170aA-1 to (ZX)-(1).170aA-514;
compounds (ZXI)-(1).170aA-1 to (ZXI)-(1).170aA-514;
compounds (ZXII)-(1).170aA-1 to (ZXII)-(1).170aA-514)
table 171a
Compounds (Z)-(1), wherein A is 2-methyl-4-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).171aA-1 to (ZI)-(1).171aA-514;
compounds (ZII)-(1).171aA-1 to (ZII)-(1).171aA-514;
compounds (ZIII)-(1).171aA-1 to (Zll l)-(1 ).171 aA-514;
compounds (ZIV)-(1).171aA-1 to (ZIV)-(1).171aA-514;
compounds (ZV)-(1).171aA-1 to (ZV)-(1).171aA-514;
compounds (ZVI)-(1).171aA-1 to (ZVI)-(1).171aA-514;
compounds (ZVII)-(1 ).171 aA-1 to (ZVII)-(1).171aA-514;
compounds (ZVIII)-(1).171aA-1 to (ZVIII)-(1).171aA-514;
compounds (ZIX)-(1).171 aA-1 to (ZIX)-(1).171aA-514;
compounds (ZX)-(1).171 aA-1 to (ZX)-(1).171aA-514;
compounds (ZXI)-(1).171 aA-1 to (ZXI)-(1).171aA-514;
compounds (ZXII)-(1).171 aA-1 to (ZXII)-(1).171aA-514)
table 172a
Compounds (Z)-(1), wherein A is 2-methyl-5-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).172aA-1 to (ZI)-(1).172aA-514;
compounds (ZII)-(1).172aA-1 to (ZII)-(1).172aA-514;
compounds (ZIII)-(1).172aA-1 to (ZIII)-(1).172aA-514;
compounds (ZIV)-(1).172aA-1 to (ZIV)-(1).172aA-514;
compounds (ZV)-(1).172aA-1 to (ZV)-(1).172aA-514;
compounds (ZVI)-(1).172aA-1 to (ZVI)-(1).172aA-514;
compounds (ZVII)-(1).172aA-1 to (ZVII)-(1).172aA-514;
compounds (ZVIII)-(1).172aA-1 to (ZVIII)-(1).172aA-514;
compounds (ZIX)-(1).172aA-1 to (ZIX)-(1).172aA-514;
compounds (ZX)-(1).172aA-1 to (ZX)-(1).172aA-514;
compounds (ZXI)-(1).172aA-1 to (ZXI)-(1).172aA-514;
compounds (ZXII)-(1).172aA-1 to (ZXII)-(1).172aA-514)
table 173a
Compounds (Z)-(1), wherein A is 2-methyl-6-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).173aA-1 to (ZI)-(1).173aA-514;
compounds (ZII)-(1).173aA-1 to (ZII)-(1).173aA-514;
compounds (ZIII)-(1).173aA-1 to (ZIII)-(1).173aA-514;
compounds (ZIV)-(1).173aA-1 to (ZIV)-(1).173aA-514;
compounds (ZV)-(1).173aA-1 to (ZV)-(1).173aA-514;
compounds (ZVI)-(1).173aA-1 to (ZVI)-(1).173aA-514;
compounds (ZVII)-(1).173aA-1 to (ZVII)-(1).173aA-514;
compounds (ZVIII)-(1).173aA-1 to (ZVIII)-(1).173aA-514;
compounds (ZIX)-(1).173aA-1 to (ZIX)-(1).173aA-514;
compounds (ZX)-(1).173aA-1 to (ZX)-(1).173aA-514;
compounds (ZXI)-(1).173aA-1 to (ZXI)-(1).173aA-514;
compounds (ZXII)-(1).173aA-1 to (ZXII)-(1).173aA-514)
table 174a
Compounds (Z)-(1), wherein A is 3-methyl-4-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).174aA-1 to (ZI)-(1).174aA-514;
compounds (ZII)-(1).174aA-1 to (ZII)-(1).174aA-514;
compounds (ZIII)-(1).174aA-1 to (ZIII)-(1).174aA-514;
compounds (ZIV)-(1).174aA-1 to (ZIV)-(1).174aA-514;
compounds (ZV)-(1).174aA-1 to (ZV)-(1).174aA-514;
compounds (ZVI)-(1).174aA-1 to (ZVI)-(1).174aA-514;
compounds (ZVII)-(1).174aA-1 to (ZVII)-(1).174aA-514;
compounds (ZVIII)-(1).174aA-1 to (ZVIII)-(1).174aA-514;
compounds (ZIX)-(1).174aA-1 to (ZIX)-(1).174aA-514;
compounds (ZX)-(1).174aA-1 to (ZX)-(1).174aA-514;
compounds (ZXI)-(1).174aA-1 to (ZXI)-(1).174aA-514;
compounds (ZXII)-(1).174aA-1 to (ZXII)-(1).174aA-514)
table 175a
Compounds (Z)-(1), wherein A is 3-methyl-5-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).175aA-1 to (ZI)-(1).175aA-514;
compounds (ZII)-(1).175aA-1 to (ZII)-(1).175aA-514;
compounds (ZIII)-(1).175aA-1 to (ZIII)-(1).175aA-514;
compounds (ZIV)-(1).175aA-1 to (ZIV)-(1).175aA-514;
compounds (ZV)-(1).175aA-1 to (ZV)-(1).175aA-514;
compounds (ZVI)-(1).175aA-1 to (ZVI)-(1).175aA-514;
compounds (ZVII)-(1).175aA-1 to (ZVII)-(1).175aA-514;
compounds (ZVIII)-(1).175aA-1 to (ZVIII)-(1).175aA-514;
compounds (ZIX)-(1).175aA-1 to (ZIX)-(1).175aA-514;
compounds (ZX)-(1).175aA-1 to (ZX)-(1).175aA-514;
compounds (ZXI)-(1).175aA-1 to (ZXI)-(1).175aA-514;
compounds (ZXII)-(1).175aA-1 to (ZXII)-(1).175aA-514)
table 176a
Compounds (Z)-(1), wherein A is 2-chloro-3-methylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).176aA-1 to (ZI)-(1).176aA-514;
compounds (ZII)-(1).176aA-1 to (ZII)-(1).176aA-514;
compounds (ZIII)-(1).176aA-1 to (ZIII)-(1).176aA-514;
compounds (ZIV)-(1).176aA-1 to (ZIV)-(1).176aA-514;
compounds (ZV)-(1).176aA-1 to (ZV)-(1).176aA-514;
compounds (ZVI)-(1).176aA-1 to (ZVI)-(1).176aA-514;
compounds (ZVII)-(1).176aA-1 to (ZVII)-(1).176aA-514;
compounds (ZVIII)-(1).176aA-1 to (ZVIII)-(1).176aA-514;
compounds (ZIX)-(1).176aA-1 to (ZIX)-(1).176aA-514;
compounds (ZX)-(1).176aA-1 to (ZX)-(1).176aA-514;
compounds (ZXI)-(1).176aA-1 to (ZXI)-(1).176aA-514;
compounds (ZXII)-(1).176aA-1 to (ZXII)-(1).176aA-514)
table 177a
Compounds (Z)-(1), wherein A is 2-chloro-4-methylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).177aA-1 to (ZI)-(1).177aA-514;
compounds (ZII)-(1).177aA-1 to (ZII)-(1).177aA-514;
compounds (ZIII)-(1).177aA-1 to (ZIII)-(1).177aA-514;
compounds (ZIV)-(1).177aA-1 to (ZIV)-(1).177aA-514;
compounds (ZV)-(1).177aA-1 to (ZV)-(1).177aA-514;
compounds (ZVI)-(1).177aA-1 to (ZVI)-(1).177aA-514;
compounds (ZVII)-(1).177aA-1 to (ZVII)-(1).177aA-514;
compounds (ZVIII)-(1).177aA-1 to (ZVIII)-(1).177aA-514;
compounds (ZIX)-(1).177aA-1 to (ZIX)-(1).177aA-514;
compounds (ZX)-(1).177aA-1 to (ZX)-(1).177aA-514;
compounds (ZXI)-(1).177aA-1 to (ZXI)-(1).177aA-514;
compounds (ZXII)-(1).177aA-1 to (ZXII)-(1).177aA-514)
table 178a
Compounds (Z)-(1), wherein A is 2-chloro-5-methylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).178aA-1 to (ZI)-(1).178aA-514;
compounds (ZII)-(1).178aA-1 to (ZII)-(1).178aA-514;
compounds (ZIII)-(1).178aA-1 to (ZIII)-(1).178aA-514;
compounds (ZIV)-(1).178aA-1 to (ZIV)-(1).178aA-514;
compounds (ZV)-(1).178aA-1 to (ZV)-(1).178aA-514;
compounds (ZVI)-(1).178aA-1 to (ZVI)-(1).178aA-514;
compounds (ZVII)-(1).178aA-1 to (ZVII)-(1).178aA-514;
compounds (ZVIII)-(1).178aA-1 to (ZVIII)-(1).178aA-514;
compounds (ZIX)-(1).178aA-1 to (ZIX)-(1).178aA-514;
compounds (ZX)-(1).178aA-1 to (ZX)-(1).178aA-514;
compounds (ZXI)-(1).178aA-1 to (ZXI)-(1).178aA-514;
compounds (ZXII)-(1).178aA-1 to (ZXII)-(1).178aA-514)
table 179a
Compounds (Z)-(1), wherein A is 3-chloro-4-methylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).179aA-1 to (ZI)-(1).179aA-514;
compounds (ZII)-(1).179aA-1 to (ZII)-(1).179aA-514;
compounds (ZIII)-(1).179aA-1 to (ZIII)-(1).179aA-514;
compounds (ZIV)-(1).179aA-1 to (ZIV)-(1).179aA-514;
compounds (ZV)-(1).179aA-1 to (ZV)-(1).179aA-514;
compounds (ZVI)-(1).179aA-1 to (ZVI)-(1).179aA-514;
compounds (ZVII)-(1).179aA-1 to (ZVII)-(1).179aA-514;
compounds (ZVIII)-(1).179aA-1 to (ZVIII)-(1).179aA-514;
compounds (ZIX)-(1).179aA-1 to (ZIX)-(1).179aA-514;
compounds (ZX)-(1).179aA-1 to (ZX)-(1).179aA-514;
compounds (ZXI)-(1).179aA-1 to (ZXI)-(1).179aA-514;
compounds (ZXII)-(1).179aA-1 to (ZXII)-(1).179aA-514)
table 180a
Compounds (Z)-(1), wherein A is 2-ethyl-3-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).180aA-1 to (ZI)-(1).180aA-514;
compounds (ZII)-(1).180aA-1 to (ZII)-(1).180aA-514;
compounds (ZIII)-(1).180aA-1 to (ZIII)-(1).180aA-514;
compounds (ZIV)-(1).180aA-1 to (ZIV)-(1).180aA-514;
compounds (ZV)-(1).180aA-1 to (ZV)-(1).180aA-514;
compounds (ZVI)-(1).180aA-1 to (ZVI)-(1).180aA-514;
compounds (ZVII)-(1).180aA-1 to (ZVII)-(1).180aA-514;
compounds (ZVIII)-(1).180aA-1 to (ZVIII)-(1).180aA-514;
compounds (ZIX)-(1).180aA-1 to (ZIX)-(1).180aA-514;
compounds (ZX)-(1).180aA-1 to (ZX)-(1).180aA-514;
compounds (ZXI)-(1).180aA-1 to (ZXI)-(1).180aA-514;
compounds (ZXII)-(1).180aA-1 to (ZXII)-(1).180aA-514)
table 181a
Compounds (Z)-(1), wherein A is 2-ethyl-4-chlorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).181 aA-1 to (ZI)-(1).181aA-514;
compounds (Zll)-(1 ).181 aA-1 to (ZII)-(1).181aA-514;
compounds (Zl ll)-(1 ).181 aA-1 to (Zll l)-(1 ).181 aA-514;
compounds (ZIV)-(1).181 aA-1 to (ZIV)-(1).181aA-514;
compounds (ZV)-(1).181 aA-1 to (ZV)-(1).181aA-514;
compounds (ZVI)-(1).181 aA-1 to (ZVI)-(1).181aA-514;
compounds (ZVII)-(1).181 aA-1 to (ZVII)-(1).181aA-514;
compounds (ZVIII)-(1).181aA-1 to (ZVIII)-(1).181aA-514;
compounds (ZIX)-(1).181 aA-1 to (ZIX)-(1).181aA-514;
compounds (ZX)-(1).181 aA-1 to (ZX)-(1).181aA-514;
compounds (ZXI)-(1).181 aA-1 to (ZXI)-(1).181aA-514;
compounds (ZXII)-(1).181 aA-1 to (ZXII)-(1).181aA-514)
table 182a
Compounds (Z)-(1), wherein A is 2-ethyl-5-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).182aA-1 to (ZI)-(1).182aA-514;
compounds (ZII)-(1).182aA-1 to (ZII)-(1).182aA-514;
compounds (ZIII)-(1).182aA-1 to (ZIII)-(1).182aA-514;
compounds (ZIV)-(1).182aA-1 to (ZIV)-(1).182aA-514;
compounds (ZV)-(1).182aA-1 to (ZV)-(1).182aA-514;
compounds (ZVI)-(1).182aA-1 to (ZVI)-(1).182aA-514;
compounds (ZVII)-(1).182aA-1 to (ZVII)-(1).182aA-514;
compounds (ZVIII)-(1).182aA-1 to (ZVIII)-(1).182aA-514;
compounds (ZIX)-(1).182aA-1 to (ZIX)-(1).182aA-514;
compounds (ZX)-(1).182aA-1 to (ZX)-(1).182aA-514;
compounds (ZXI)-(1).182aA-1 to (ZXI)-(1).182aA-514;
compounds (ZXII)-(1).182aA-1 to (ZXII)-(1).182aA-514)
table 183a
Compounds (Z)-(1), wherein A is 2-ethyl-6-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).183aA-1 to (ZI)-(1).183aA-514;
compounds (ZII)-(1).183aA-1 to (ZII)-(1).183aA-514;
compounds (ZIII)-(1).183aA-1 to (ZIII)-(1).183aA-514;
compounds (ZIV)-(1).183aA-1 to (ZIV)-(1).183aA-514;
compounds (ZV)-(1).183aA-1 to (ZV)-(1).183aA-514;
compounds (ZVI)-(1).183aA-1 to (ZVI)-(1).183aA-514;
compounds (ZVII)-(1).183aA-1 to (ZVII)-(1).183aA-514;
compounds (ZVIII)-(1).183aA-1 to (ZVIII)-(1).183aA-514;
compounds (ZIX)-(1).183aA-1 to (ZIX)-(1).183aA-514;
compounds (ZX)-(1).183aA-1 to (ZX)-(1).183aA-514;
compounds (ZXI)-(1).183aA-1 to (ZXI)-(1).183aA-514;
compounds (ZXII)-(1).183aA-1 to (ZXII)-(1).183aA-514)
table 184a
Compounds (Z)-(1), wherein A is 3-ethyl-4-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).184aA-1 to (ZI)-(1).184aA-514;
compounds (ZII)-(1).184aA-1 to (ZII)-(1).184aA-514;
compounds (ZIII)-(1).184aA-1 to (ZIII)-(1).184aA-514;
compounds (ZIV)-(1).184aA-1 to (ZIV)-(1).184aA-514;
compounds (ZV)-(1).184aA-1 to (ZV)-(1).184aA-514;
compounds (ZVI)-(1).184aA-1 to (ZVI)-(1).184aA-514;
compounds (ZVII)-(1).184aA-1 to (ZVII)-(1).184aA-514;
compounds (ZVIII)-(1).184aA-1 to (ZVIII)-(1).184aA-514;
compounds (ZIX)-(1).184aA-1 to (ZIX)-(1).184aA-514;
compounds (ZX)-(1).184aA-1 to (ZX)-(1).184aA-514;
compounds (ZXI)-(1).184aA-1 to (ZXI)-(1).184aA-514;
compounds (ZXII)-(1).184aA-1 to (ZXII)-(1).184aA-514)
table 185a
Compounds (Z)-(1), wherein A is 3-ethyl-5-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).185aA-1 to (ZI)-(1).185aA-514;
compounds (ZII)-(1).185aA-1 to (ZII)-(1).185aA-514;
compounds (ZIII)-(1).185aA-1 to (ZIII)-(1).185aA-514;
compounds (ZIV)-(1).185aA-1 to (ZIV)-(1).185aA-514;
compounds (ZV)-(1).185aA-1 to (ZV)-(1).185aA-514;
compounds (ZVI)-(1).185aA-1 to (ZVI)-(1).185aA-514;
compounds (ZVII)-(1).185aA-1 to (ZVII)-(1).185aA-514;
compounds (ZVIII)-(1).185aA-1 to (ZVIII)-(1).185aA-514;
compounds (ZIX)-(1).185aA-1 to (ZIX)-(1).185aA-514;
compounds (ZX)-(1).185aA-1 to (ZX)-(1).185aA-514;
compounds (ZXI)-(1).185aA-1 to (ZXI)-(1).185aA-514;
compounds (ZXII)-(1).185aA-1 to (ZXII)-(1).185aA-514)
table 186a
Compounds (Z)-(1), wherein A is 2-chloro-3-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).186aA-1 to (ZI)-(1).186aA-514;
compounds (ZII)-(1).186aA-1 to (ZII)-(1).186aA-514;
compounds (ZIII)-(1).186aA-1 to (ZIII)-(1).186aA-514;
compounds (ZIV)-(1).186aA-1 to (ZIV)-(1).186aA-514;
compounds (ZV)-(1).186aA-1 to (ZV)-(1).186aA-514;
compounds (ZVI)-(1).186aA-1 to (ZVI)-(1).186aA-514;
compounds (ZVII)-(1).186aA-1 to (ZVII)-(1).186aA-514;
compounds (ZVIII)-(1).186aA-1 to (ZVIII)-(1).186aA-514;
compounds (ZIX)-(1).186aA-1 to (ZIX)-(1).186aA-514;
compounds (ZX)-(1).186aA-1 to (ZX)-(1).186aA-514;
compounds (ZXI)-(1).186aA-1 to (ZXI)-(1).186aA-514;
compounds (ZXII)-(1).186aA-1 to (ZXII)-(1).186aA-514)
table 187a
Compounds (Z)-(1), wherein A is 2-chloro-4-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).187aA-1 to (ZI)-(1).187aA-514;
compounds (ZII)-(1).187aA-1 to (ZII)-(1).187aA-514;
compounds (ZIII)-(1).187aA-1 to (ZIII)-(1).187aA-514;
compounds (ZIV)-(1).187aA-1 to (ZIV)-(1).187aA-514;
compounds (ZV)-(1).187aA-1 to (ZV)-(1).187aA-514;
compounds (ZVI)-(1).187aA-1 to (ZVI)-(1).187aA-514;
compounds (ZVII)-(1).187aA-1 to (ZVII)-(1).187aA-514;
compounds (ZVIII)-(1).187aA-1 to (ZVIII)-(1).187aA-514;
compounds (ZIX)-(1).187aA-1 to (ZIX)-(1).187aA-514;
compounds (ZX)-(1).187aA-1 to (ZX)-(1).187aA-514;
compounds (ZXI)-(1).187aA-1 to (ZXI)-(1).187aA-514;
compounds (ZXII)-(1).187aA-1 to (ZXII)-(1).187aA-514)
table 188a
Compounds (Z)-(1), wherein A is 2-chloro-5-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).188aA-1 to (ZI)-(1).188aA-514;
compounds (ZII)-(1).188aA-1 to (ZII)-(1).188aA-514;
compounds (ZIII)-(1).188aA-1 to (ZIII)-(1).188aA-514;
compounds (ZIV)-(1).188aA-1 to (ZIV)-(1).188aA-514;
compounds (ZV)-(1).188aA-1 to (ZV)-(1).188aA-514;
compounds (ZVI)-(1).188aA-1 to (ZVI)-(1).188aA-514;
compounds (ZVII)-(1).188aA-1 to (ZVII)-(1).188aA-514;
compounds (ZVIII)-(1).188aA-1 to (ZVIII)-(1).188aA-514;
compounds (ZIX)-(1).188aA-1 to (ZIX)-(1).188aA-514;
compounds (ZX)-(1).188aA-1 to (ZX)-(1).188aA-514;
compounds (ZXI)-(1).188aA-1 to (ZXI)-(1).188aA-514;
compounds (ZXII)-(1).188aA-1 to (ZXII)-(1).188aA-514)
table 189a
Compounds (Z)-(1), wherein A is 3-chloro-4-ethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).189aA-1 to (ZI)-(1).189aA-514;
compounds (ZII)-(1).189aA-1 to (ZII)-(1).189aA-514;
compounds (ZIII)-(1).189aA-1 to (ZIII)-(1).189aA-514;
compounds (ZIV)-(1).189aA-1 to (ZIV)-(1).189aA-514;
compounds (ZV)-(1).189aA-1 to (ZV)-(1).189aA-514;
compounds (ZVI)-(1).189aA-1 to (ZVI)-(1).189aA-514;
compounds (ZVII)-(1).189aA-1 to (ZVII)-(1).189aA-514;
compounds (ZVIII)-(1).189aA-1 to (ZVIII)-(1).189aA-514;
compounds (ZIX)-(1).189aA-1 to (ZIX)-(1).189aA-514;
compounds (ZX)-(1).189aA-1 to (ZX)-(1).189aA-514;
compounds (ZXI)-(1).189aA-1 to (ZXI)-(1).189aA-514;
compounds (ZXII)-(1).189aA-1 to (ZXII)-(1).189aA-514)
table 190a
Compounds (Z)-(1), wherein A is 2-methoxy-3-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).190aA-1 to (ZI)-(1).190aA-514;
compounds (ZII)-(1).190aA-1 to (ZII)-(1).190aA-514;
compounds (ZIII)-(1).190aA-1 to (ZIII)-(1).190aA-514;
compounds (ZIV)-(1).190aA-1 to (ZIV)-(1).190aA-514;
compounds (ZV)-(1).190aA-1 to (ZV)-(1).190aA-514;
compounds (ZVI)-(1).190aA-1 to (ZVI)-(1).190aA-514;
compounds (ZVII)-(1).190aA-1 to (ZVII)-(1).190aA-514;
compounds (ZVIII)-(1).190aA-1 to (ZVIII)-(1).190aA-514;
compounds (ZIX)-(1).190aA-1 to (ZIX)-(1).190aA-514;
compounds (ZX)-(1).190aA-1 to (ZX)-(1).190aA-514;
compounds (ZXI)-(1).190aA-1 to (ZXI)-(1).190aA-514;
compounds (ZXII)-(1).190aA-1 to (ZXII)-(1).190aA-514)
table 191a
Compounds (Z)-(1), wherein A is 2-methoxy-4-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).191aA-1 to (ZI)-(1).191aA-514;
compounds (ZII)-(1).191aA-1 to (ZII)-(1).191aA-514;
compounds (ZIII)-(1).191aA-1 to (Zlll)-(1 ).191 aA-514;
compounds (ZIV)-(1).191aA-1 to (ZIV)-(1).191aA-514;
compounds (ZV)-(1).191aA-1 to (ZV)-(1).191aA-514;
compounds (ZVI)-(1).191aA-1 to (ZVI)-(1).191aA-514;
compounds (ZVII)-(1 ).191 aA-1 to (ZVII)-(1).191aA-514;
compounds (ZVIII)-(1).191aA-1 to (ZVIII)-(1).191aA-514;
compounds (ZIX)-(1).191aA-1 to (ZIX)-(1).191aA-514;
compounds (ZX)-(1).191aA-1 to (ZX)-(1).191aA-514;
compounds (ZXI)-(1).191aA-1 to (ZXI)-(1).191aA-514;
compounds (ZXII)-(1).191aA-1 to (ZXII)-(1).191aA-514)
table 192a
Compounds (Z)-(1), wherein A is 2-methoxy-5-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).192aA-1 to (ZI)-(1).192aA-514;
compounds (ZII)-(1).192aA-1 to (ZII)-(1).192aA-514;
compounds (ZIII)-(1).192aA-1 to (ZIII)-(1).192aA-514;
compounds (ZIV)-(1).192aA-1 to (ZIV)-(1).192aA-514;
compounds (ZV)-(1).192aA-1 to (ZV)-(1).192aA-514;
compounds (ZVI)-(1).192aA-1 to (ZVI)-(1).192aA-514;
compounds (ZVII)-(1).192aA-1 to (ZVII)-(1).192aA-514;
compounds (ZVIII)-(1).192aA-1 to (ZVIII)-(1).192aA-514;
compounds (ZIX)-(1).192aA-1 to (ZIX)-(1).192aA-514;
compounds (ZX)-(1).192aA-1 to (ZX)-(1).192aA-514;
compounds (ZXI)-(1).192aA-1 to (ZXI)-(1).192aA-514;
compounds (ZXII)-(1).192aA-1 to (ZXII)-(1).192aA-514)
table 193a
Compounds (Z)-(1), wherein A is 2-methoxy-6-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).193aA-1 to (ZI)-(1).193aA-514;
compounds (ZII)-(1).193aA-1 to (ZII)-(1).193aA-514;
compounds (ZIII)-(1).193aA-1 to (ZIII)-(1).193aA-514;
compounds (ZIV)-(1).193aA-1 to (ZIV)-(1).193aA-514;
compounds (ZV)-(1).193aA-1 to (ZV)-(1).193aA-514;
compounds (ZVI)-(1).193aA-1 to (ZVI)-(1).193aA-514;
compounds (ZVII)-(1).193aA-1 to (ZVII)-(1).193aA-514;
compounds (ZVIII)-(1).193aA-1 to (ZVIII)-(1).193aA-514;
compounds (ZIX)-(1).193aA-1 to (ZIX)-(1).193aA-514;
compounds (ZX)-(1).193aA-1 to (ZX)-(1).193aA-514;
compounds (ZXI)-(1).193aA-1 to (ZXI)-(1).193aA-514;
compounds (ZXII)-(1).193aA-1 to (ZXII)-(1).193aA-514)
table 194a
Compounds (Z)-(1), wherein A is 3-methoxy-4-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).194aA-1 to (ZI)-(1).194aA-514;
compounds (ZII)-(1).194aA-1 to (ZII)-(1).194aA-514;
compounds (ZIII)-(1).194aA-1 to (ZIII)-(1).194aA-514;
compounds (ZIV)-(1).194aA-1 to (ZIV)-(1).194aA-514;
compounds (ZV)-(1).194aA-1 to (ZV)-(1).194aA-514;
compounds (ZVI)-(1).194aA-1 to (ZVI)-(1).194aA-514;
compounds (ZVII)-(1).194aA-1 to (ZVII)-(1).194aA-514;
compounds (ZVIII)-(1).194aA-1 to (ZVIII)-(1).194aA-514;
compounds (ZIX)-(1).194aA-1 to (ZIX)-(1).194aA-514;
compounds (ZX)-(1).194aA-1 to (ZX)-(1).194aA-514;
compounds (ZXI)-(1).194aA-1 to (ZXI)-(1).194aA-514;
compounds (ZXII)-(1).194aA-1 to (ZXII)-(1).194aA-514)
table 195a
Compounds (Z)-(1), wherein A is 3-methoxy-5-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).195aA-1 to (ZI)-(1).195aA-514;
compounds (ZII)-(1).195aA-1 to (ZII)-(1).195aA-514;
compounds (ZIII)-(1).195aA-1 to (ZIII)-(1).195aA-514;
compounds (ZIV)-(1).195aA-1 to (ZIV)-(1).195aA-514;
compounds (ZV)-(1).195aA-1 to (ZV)-(1).195aA-514;
compounds (ZVI)-(1).195aA-1 to (ZVI)-(1).195aA-514;
compounds (ZVII)-(1).195aA-1 to (ZVII)-(1).195aA-514;
compounds (ZVIII)-(1).195aA-1 to (ZVIII)-(1).195aA-514;
compounds (ZIX)-(1).195aA-1 to (ZIX)-(1).195aA-514;
compounds (ZX)-(1).195aA-1 to (ZX)-(1).195aA-514;
compounds (ZXI)-(1).195aA-1 to (ZXI)-(1).195aA-514;
compounds (ZXII)-(1).195aA-1 to (ZXII)-(1).195aA-514)
table 196a
Compounds (Z)-(1), wherein A is 2-chloro-3-methoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).196aA-1 to (ZI)-(1).196aA-514;
compounds (ZII)-(1).196aA-1 to (ZII)-(1).196aA-514;
compounds (ZIII)-(1).196aA-1 to (ZIII)-(1).196aA-514;
compounds (ZIV)-(1).196aA-1 to (ZIV)-(1).196aA-514;
compounds (ZV)-(1).196aA-1 to (ZV)-(1).196aA-514;
compounds (ZVI)-(1).196aA-1 to (ZVI)-(1).196aA-514;
compounds (ZVII)-(1).196aA-1 to (ZVII)-(1).196aA-514;
compounds (ZVIII)-(1).196aA-1 to (ZVIII)-(1).196aA-514;
compounds (ZIX)-(1).196aA-1 to (ZIX)-(1).196aA-514;
compounds (ZX)-(1).196aA-1 to (ZX)-(1).196aA-514;
compounds (ZXI)-(1).196aA-1 to (ZXI)-(1).196aA-514;
compounds (ZXII)-(1).196aA-1 to (ZXII)-(1).196aA-514)
table 197a
Compounds (Z)-(1), wherein A is 2-chloro-4-methoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).197aA-1 to (ZI)-(1).197aA-514;
compounds (ZII)-(1).197aA-1 to (ZII)-(1).197aA-514;
compounds (ZIII)-(1).197aA-1 to (ZIII)-(1).197aA-514;
compounds (ZIV)-(1).197aA-1 to (ZIV)-(1).197aA-514;
compounds (ZV)-(1).197aA-1 to (ZV)-(1).197aA-514;
compounds (ZVI)-(1).197aA-1 to (ZVI)-(1).197aA-514;
compounds (ZVII)-(1).197aA-1 to (ZVII)-(1).197aA-514;
compounds (ZVIII)-(1).197aA-1 to (ZVIII)-(1).197aA-514;
compounds (ZIX)-(1).197aA-1 to (ZIX)-(1).197aA-514;
compounds (ZX)-(1).197aA-1 to (ZX)-(1).197aA-514;
compounds (ZXI)-(1).197aA-1 to (ZXI)-(1).197aA-514;
compounds (ZXII)-(1).197aA-1 to (ZXII)-(1).197aA-514)
table 198a
Compounds (Z)-(1), wherein A is 2-chloro-5-methoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).198aA-1 to (ZI)-(1).198aA-514;
compounds (ZII)-(1).198aA-1 to (ZII)-(1).198aA-514;
compounds (ZIII)-(1).198aA-1 to (ZIII)-(1).198aA-514;
compounds (ZIV)-(1).198aA-1 to (ZIV)-(1).198aA-514;
compounds (ZV)-(1).198aA-1 to (ZV)-(1).198aA-514;
compounds (ZVI)-(1).198aA-1 to (ZVI)-(1).198aA-514;
compounds (ZVII)-(1).198aA-1 to (ZVII)-(1).198aA-514;
compounds (ZVIII)-(1).198aA-1 to (ZVIII)-(1).198aA-514;
compounds (ZIX)-(1).198aA-1 to (ZIX)-(1).198aA-514;
compounds (ZX)-(1).198aA-1 to (ZX)-(1).198aA-514;
compounds (ZXI)-(1).198aA-1 to (ZXI)-(1).198aA-514;
compounds (ZXII)-(1).198aA-1 to (ZXII)-(1).198aA-514)
table 199a
Compounds (Z)-(1), wherein A is 3-chloro-4-methoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).199aA-1 to (ZI)-(1).199aA-514;
compounds (ZII)-(1).199aA-1 to (ZII)-(1).199aA-514;
compounds (ZIII)-(1).199aA-1 to (ZIII)-(1).199aA-514;
compounds (ZIV)-(1).199aA-1 to (ZIV)-(1).199aA-514;
compounds (ZV)-(1).199aA-1 to (ZV)-(1).199aA-514;
compounds (ZVI)-(1).199aA-1 to (ZVI)-(1).199aA-514;
compounds (ZVII)-(1).199aA-1 to (ZVII)-(1).199aA-514;
compounds (ZVIII)-(1).199aA-1 to (ZVIII)-(1).199aA-514;
compounds (ZIX)-(1).199aA-1 to (ZIX)-(1).199aA-514;
compounds (ZX)-(1).199aA-1 to (ZX)-(1).199aA-514;
compounds (ZXI)-(1).199aA-1 to (ZXI)-(1).199aA-514;
compounds (ZXII)-(1).199aA-1 to (ZXII)-(1).199aA-514)
table 200a
Compounds (Z)-(1), wherein A is 2-(trifluoromethyl)-3-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).200aA-1 to (ZI)-(1).200aA-514; compounds (ZII)-(1).200aA-1 to (ZII)-(1).200aA-514;
compounds (ZIII)-(1).200aA-1 to (ZIII)-(1).200aA-514;
compounds (ZIV)-(1).200aA-1 to (ZIV)-(1).200aA-514;
compounds (ZV)-(1 ).200aA-1 to (ZV)-(1 ).200aA-514;
compounds (ZVI)-(1).200aA-1 to (ZVI)-(1).200aA-514;
compounds (ZVII)-(1).200aA-1 to (ZVII)-(1).200aA-514;
compounds (ZVIII)-(1).200aA-1 to (ZVIII)-(1).200aA-514;
compounds (ZIX)-(1).200aA-1 to (ZIX)-(1).200aA-514;
compounds (ZX)-(1 ).200aA-1 to (ZX)-(1 ).200aA-514;
compounds (ZXI)-(1).200aA-1 to (ZXI)-(1).200aA-514;
compounds (ZXII)-(1).200aA-1 to (ZXII)-(1).200aA-514)
table 201a
Compounds (Z)-(1), wherein A is 2-(trifluoromethyl)-4-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).201aA-1 to (ZI)-(1).201aA-514; compounds (ZII)-(1).201aA-1 to (ZII)-(1).201aA-514;
compounds (ZIII)-(1).201aA-1 to (Zll l)-(1 ).201 aA-514;
compounds (ZIV)-(1).201aA-1 to (ZIV)-(1).201aA-514;
compounds (ZV)-(1).201aA-1 to (ZV)-(1).201aA-514;
compounds (ZVI)-(1).201aA-1 to (ZVI)-(1).201aA-514;
compounds (ZVII)-(1).201aA-1 to (ZVII)-(1).201aA-514;
compounds (ZVIII)-(1).201aA-1 to (ZVIII)-(1).201aA-514;
compounds (ZIX)-(1).201aA-1 to (ZIX)-(1).201aA-514;
compounds (ZX)-(1).201aA-1 to (ZX)-(1).201aA-514;
compounds (ZXI)-(1).201aA-1 to (ZXI)-(1).201aA-514;
compounds (ZXII)-(1).201aA-1 to (ZXII)-(1).201aA-514)
table 202a
Compounds (Z)-(1), wherein A is 2-(trifluoromethyl)-5-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).202aA-1 to (ZI)-(1).202aA-514; compounds (ZII)-(1).202aA-1 to (ZII)-(1).202aA-514;
compounds (ZIII)-(1).202aA-1 to (ZIII)-(1).202aA-514;
compounds (ZIV)-(1).202aA-1 to (ZIV)-(1).202aA-514;
compounds (ZV)-(1).202aA-1 to (ZV)-(1).202aA-514;
compounds (ZVI)-(1).202aA-1 to (ZVI)-(1).202aA-514;
compounds (ZVII)-(1).202aA-1 to (ZVII)-(1).202aA-514;
compounds (ZVIII)-(1).202aA-1 to (ZVIII)-(1).202aA-514;
compounds (ZIX)-(1).202aA-1 to (ZIX)-(1).202aA-514;
compounds (ZX)-(1).202aA-1 to (ZX)-(1).202aA-514;
compounds (ZXI)-(1).202aA-1 to (ZXI)-(1).202aA-514;
compounds (ZXII)-(1).202aA-1 to (ZXII)-(1).202aA-514)
table 203a
Compounds (Z)-(1), wherein A is 2-(trifluoromethyl)-6-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).203aA-1 to (ZI)-(1).203aA-514; compounds (ZII)-(1).203aA-1 to (ZII)-(1).203aA-514;
compounds (ZIII)-(1).203aA-1 to (ZIII)-(1).203aA-514;
compounds (ZIV)-(1).203aA-1 to (ZIV)-(1).203aA-514;
compounds (ZV)-(1 ).203aA-1 to (ZV)-(1 ).203aA-514;
compounds (ZVI)-(1).203aA-1 to (ZVI)-(1).203aA-514;
compounds (ZVII)-(1).203aA-1 to (ZVII)-(1).203aA-514;
compounds (ZVIII)-(1).203aA-1 to (ZVIII)-(1).203aA-514;
compounds (ZIX)-(1).203aA-1 to (ZIX)-(1).203aA-514;
compounds (ZX)-(1 ).203aA-1 to (ZX)-(1 ).203aA-514;
compounds (ZXI)-(1).203aA-1 to (ZXI)-(1).203aA-514;
compounds (ZXII)-(1).203aA-1 to (ZXII)-(1).203aA-514)
table 204a
Compounds (Z)-(1), wherein A is 3-(trifluoromethyl)-4-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).204aA-1 to (ZI)-(1).204aA-514; compounds (ZII)-(1).204aA-1 to (ZII)-(1).204aA-514;
compounds (ZIII)-(1).204aA-1 to (ZIII)-(1).204aA-514;
compounds (ZIV)-(1).204aA-1 to (ZIV)-(1).204aA-514;
compounds (ZV)-(1).204aA-1 to (ZV)-(1).204aA-514;
compounds (ZVI)-(1).204aA-1 to (ZVI)-(1).204aA-514;
compounds (ZVII)-(1).204aA-1 to (ZVII)-(1).204aA-514;
compounds (ZVIII)-(1).204aA-1 to (ZVIII)-(1).204aA-514;
compounds (ZIX)-(1).204aA-1 to (ZIX)-(1).204aA-514;
compounds (ZX)-(1).204aA-1 to (ZX)-(1).204aA-514;
compounds (ZXI)-(1).204aA-1 to (ZXI)-(1).204aA-514;
compounds (ZXII)-(1).204aA-1 to (ZXII)-(1).204aA-514)
table 205a
Compounds (Z)-(1), wherein A is 3-(trifluoromethyl)-5-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).205aA-1 to (ZI)-(1).205aA-514; compounds (ZII)-(1).205aA-1 to (ZII)-(1).205aA-514;
compounds (ZIII)-(1).205aA-1 to (ZIII)-(1).205aA-514;
compounds (ZIV)-(1).205aA-1 to (ZIV)-(1).205aA-514;
compounds (ZV)-(1).205aA-1 to (ZV)-(1).205aA-514;
compounds (ZVI)-(1).205aA-1 to (ZVI)-(1).205aA-514;
compounds (ZVII)-(1).205aA-1 to (ZVII)-(1).205aA-514;
compounds (ZVIII)-(1).205aA-1 to (ZVIII)-(1).205aA-514;
compounds (ZIX)-(1).205aA-1 to (ZIX)-(1).205aA-514;
compounds (ZX)-(1).205aA-1 to (ZX)-(1).205aA-514;
compounds (ZXI)-(1).205aA-1 to (ZXI)-(1).205aA-514;
compounds (ZXII)-(1).205aA-1 to (ZXII)-(1).205aA-514)
table 206a
Compounds (Z)-(1), wherein A is 2-chloro-3-(trifluoromethyl)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).206aA-1 to (ZI)-(1).206aA-514; compounds (ZII)-(1).206aA-1 to (ZII)-(1).206aA-514;
compounds (ZIII)-(1).206aA-1 to (ZIII)-(1).206aA-514;
compounds (ZIV)-(1).206aA-1 to (ZIV)-(1).206aA-514;
compounds (ZV)-(1 ).206aA-1 to (ZV)-(1 ).206aA-514;
compounds (ZVI)-(1).206aA-1 to (ZVI)-(1).206aA-514;
compounds (ZVII)-(1).206aA-1 to (ZVII)-(1).206aA-514;
compounds (ZVIII)-(1).206aA-1 to (ZVIII)-(1).206aA-514;
compounds (ZIX)-(1).206aA-1 to (ZIX)-(1).206aA-514;
compounds (ZX)-(1 ).206aA-1 to (ZX)-(1 ).206aA-514;
compounds (ZXI)-(1).206aA-1 to (ZXI)-(1).206aA-514;
compounds (ZXII)-(1).206aA-1 to (ZXII)-(1).206aA-514)
table 207a
Compounds (Z)-(1), wherein A is 2-chloro-4-(trifluoromethyl)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).207aA-1 to (ZI)-(1).207aA-514; compounds (ZII)-(1).207aA-1 to (ZII)-(1).207aA-514;
compounds (ZIII)-(1).207aA-1 to (ZIII)-(1).207aA-514;
compounds (ZIV)-(1).207aA-1 to (ZIV)-(1).207aA-514;
compounds (ZV)-(1).207aA-1 to (ZV)-(1).207aA-514;
compounds (ZVI)-(1).207aA-1 to (ZVI)-(1).207aA-514;
compounds (ZVII)-(1).207aA-1 to (ZVII)-(1).207aA-514;
compounds (ZVIII)-(1).207aA-1 to (ZVIII)-(1).207aA-514;
compounds (ZIX)-(1).207aA-1 to (ZIX)-(1).207aA-514;
compounds (ZX)-(1).207aA-1 to (ZX)-(1).207aA-514;
compounds (ZXI)-(1).207aA-1 to (ZXI)-(1).207aA-514;
compounds (ZXII)-(1).207aA-1 to (ZXII)-(1).207aA-514)
table 208a
Compounds (Z)-(1), wherein A is 2-chloro-5-(trifluoromethyl)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).208aA-1 to (ZI)-(1).208aA-514; compounds (ZII)-(1).208aA-1 to (ZII)-(1).208aA-514;
compounds (ZIII)-(1).208aA-1 to (ZIII)-(1).208aA-514;
compounds (ZIV)-(1).208aA-1 to (ZIV)-(1).208aA-514;
compounds (ZV)-(1).208aA-1 to (ZV)-(1).208aA-514;
compounds (ZVI)-(1).208aA-1 to (ZVI)-(1).208aA-514;
compounds (ZVII)-(1).208aA-1 to (ZVII)-(1).208aA-514;
compounds (ZVIII)-(1).208aA-1 to (ZVIII)-(1).208aA-514;
compounds (ZIX)-(1).208aA-1 to (ZIX)-(1).208aA-514;
compounds (ZX)-(1).208aA-1 to (ZX)-(1).208aA-514;
compounds (ZXI)-(1).208aA-1 to (ZXI)-(1).208aA-514;
compounds (ZXII)-(1).208aA-1 to (ZXII)-(1).208aA-514)
table 209a
Compounds (Z)-(1), wherein A is 3-chloro-4-(trifluoromethyl)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).209aA-1 to (ZI)-(1).209aA-514; compounds (ZII)-(1).209aA-1 to (ZII)-(1).209aA-514;
compounds (ZIII)-(1).209aA-1 to (ZIII)-(1).209aA-514;
compounds (ZIV)-(1).209aA-1 to (ZIV)-(1).209aA-514;
compounds (ZV)-(1 ).209aA-1 to (ZV)-(1 ).209aA-514;
compounds (ZVI)-(1).209aA-1 to (ZVI)-(1).209aA-514;
compounds (ZVII)-(1).209aA-1 to (ZVII)-(1).209aA-514;
compounds (ZVIII)-(1).209aA-1 to (ZVIII)-(1).209aA-514;
compounds (ZIX)-(1).209aA-1 to (ZIX)-(1).209aA-514;
compounds (ZX)-(1 ).209aA-1 to (ZX)-(1 ).209aA-514;
compounds (ZXI)-(1).209aA-1 to (ZXI)-(1).209aA-514;
compounds (ZXII)-(1).209aA-1 to (ZXII)-(1).209aA-514)
table 210a
Compounds (Z)-(1), wherein A is 2-(trifluoromethoxy)-3-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).210aA-1 to (ZI)-(1).210aA-514; compounds (Zll)-(1 ).210aA-1 to (Zll)-(1 ).21 OaA-514;
compounds (Zlll)-(1 ).210aA-1 to (Zll l)-(1 ).21 OaA-514;
compounds (ZIV)-(1).210aA-1 to (ZIV)-(1).210aA-514;
compounds (ZV)-(1).210aA-1 to (ZV)-(1).21 OaA-514;
compounds (ZVI)-(1).210aA-1 to (ZVI)-(1).21 OaA-514;
compounds (ZVII)-(1).210aA-1 to (ZVII)-(1).210aA-514;
compounds (ZVIII)-(1 ).210aA-1 to (ZVIII)-(1).210aA-514;
compounds (ZIX)-(1).210aA-1 to (ZIX)-(1).210aA-514;
compounds (ZX)-(1).210aA-1 to (ZX)-(1).21 OaA-514;
compounds (ZXI)-(1).210aA-1 to (ZXI)-(1).210aA-514;
compounds (ZXII)-(1).210aA-1 to (ZXII)-(1).21 OaA-514)
table 211a
Compounds (Z)-(1), wherein A is 2-(trifluoromethoxy)-4-chlorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).211 aA-1 to (Zl)-(1).211aA-514; compounds (Zll)-(1 ).211 aA-1 to (Zll)-(1 ).211 aA-514;
compounds (ZIII)-(1).211aA-1 to (Zll l)-(1 ).211 aA-514;
compounds (ZIV)-(1).211aA-1 to (ZIV)-(1).211aA-514;
compounds (ZV)-(1).211aA-1 to (ZV)-(1).211aA-514;
compounds (ZVI)-(1).211aA-1 to (ZVI)-(1).211aA-514;
compounds (ZVII)-(1 ).211 aA-1 to (ZVII)-(1).211aA-514;
compounds (ZVIII)-(1).211aA-1 to (ZVIII)-(1 ).21 aA-514;
compounds (ZIX)-(1).211aA-1 to (ZIX)-(1).211aA-514;
compounds (ZX)-(1).211aA-1 to (ZX)-(1).211aA-514;
compounds (ZXI)-(1).211aA-1 to (ZXI)-(1).211aA-514;
compounds (ZXII)-(1).211aA-1 to (ZXII)-(1).211aA-514)
table 212a
Compounds (Z)-(1), wherein A is 2-(trifluoromethoxy)-5-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).212aA-1 to (ZI)-(1).212aA-514; compounds (ZII)-(1).212aA-1 to (ZII)-(1).212aA-514;
compounds (ZIII)-(1).212aA-1 to (ZIII)-(1).212aA-514;
compounds (ZIV)-(1).212aA-1 to (ZIV)-(1).212aA-514;
compounds (ZV)-(1).212aA-1 to (ZV)-(1).212aA-514;
compounds (ZVI)-(1).212aA-1 to (ZVI)-(1).212aA-514;
compounds (ZVII)-(1).212aA-1 to (ZVII)-(1).212aA-514;
compounds (ZVIII)-(1).212aA-1 to (ZVIII)-(1).212aA-514;
compounds (ZIX)-(1).212aA-1 to (ZIX)-(1).212aA-514;
compounds (ZX)-(1 ).212aA-1 to (ZX)-(1 ).212aA-514;
compounds (ZXI)-(1).212aA-1 to (ZXI)-(1).212aA-514;
compounds (ZXII)-(1).212aA-1 to (ZXII)-(1).212aA-514)
table 213a
Compounds (Z)-(1), wherein A is 2-(trifluoromethoxy)-6-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).213aA-1 to (ZI)-(1).213aA-514; compounds (ZII)-(1).213aA-1 to (ZII)-(1).213aA-514;
compounds (ZIII)-(1).213aA-1 to (ZIII)-(1).213aA-514;
compounds (ZIV)-(1).213aA-1 to (ZIV)-(1).213aA-514;
compounds (ZV)-(1).213aA-1 to (ZV)-(1).213aA-514;
compounds (ZVI)-(1).213aA-1 to (ZVI)-(1).213aA-514;
compounds (ZVII)-(1).213aA-1 to (ZVII)-(1).213aA-514;
compounds (ZVIII)-(1).213aA-1 to (ZVIII)-(1).213aA-514;
compounds (ZIX)-(1).213aA-1 to (ZIX)-(1).213aA-514;
compounds (ZX)-(1).213aA-1 to (ZX)-(1).213aA-514;
compounds (ZXI)-(1).213aA-1 to (ZXI)-(1).213aA-514;
compounds (ZXII)-(1).213aA-1 to (ZXII)-(1).213aA-514)
table 214a
Compounds (Z)-(1), wherein A is 3-(trifluoromethoxy)-4-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).214aA-1 to (ZI)-(1).214aA-514; compounds (ZII)-(1).214aA-1 to (ZII)-(1).214aA-514;
compounds (ZIII)-(1).214aA-1 to (ZIII)-(1).214aA-514;
compounds (ZIV)-(1).214aA-1 to (ZIV)-(1).214aA-514;
compounds (ZV)-(1).214aA-1 to (ZV)-(1).214aA-514;
compounds (ZVI)-(1).214aA-1 to (ZVI)-(1).214aA-514;
compounds (ZVII)-(1).214aA-1 to (ZVII)-(1).214aA-514;
compounds (ZVIII)-(1).214aA-1 to (ZVIII)-(1).214aA-514;
compounds (ZIX)-(1).214aA-1 to (ZIX)-(1).214aA-514;
compounds (ZX)-(1).214aA-1 to (ZX)-(1).214aA-514;
compounds (ZXI)-(1).214aA-1 to (ZXI)-(1).214aA-514;
compounds (ZXII)-(1).214aA-1 to (ZXII)-(1).214aA-514)
table 215a
Compounds (Z)-(1), wherein A is 3-(trifluoromethoxy)-5-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).215aA-1 to (ZI)-(1).215aA-514; compounds (ZII)-(1).215aA-1 to (ZII)-(1).215aA-514;
compounds (ZIII)-(1).215aA-1 to (ZIII)-(1).215aA-514;
compounds (ZIV)-(1).215aA-1 to (ZIV)-(1).215aA-514;
compounds (ZV)-(1).215aA-1 to (ZV)-(1).215aA-514;
compounds (ZVI)-(1).215aA-1 to (ZVI)-(1).215aA-514;
compounds (ZVII)-(1).215aA-1 to (ZVII)-(1).215aA-514;
compounds (ZVIII)-(1).215aA-1 to (ZVIII)-(1).215aA-514;
compounds (ZIX)-(1).215aA-1 to (ZIX)-(1).215aA-514;
compounds (ZX)-(1).215aA-1 to (ZX)-(1).215aA-514;
compounds (ZXI)-(1).215aA-1 to (ZXI)-(1).215aA-514;
compounds (ZXII)-(1).215aA-1 to (ZXII)-(1).215aA-514)
table 216a
Compounds (Z)-(1), wherein A is 2-chloro-3-(trifluoromethoxy)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).216aA-1 to (ZI)-(1).216aA-514; compounds (ZII)-(1).216aA-1 to (ZII)-(1).216aA-514;
compounds (ZIII)-(1).216aA-1 to (ZIII)-(1).216aA-514;
compounds (ZIV)-(1).216aA-1 to (ZIV)-(1).216aA-514;
compounds (ZV)-(1).216aA-1 to (ZV)-(1).216aA-514;
compounds (ZVI)-(1).216aA-1 to (ZVI)-(1).216aA-514;
compounds (ZVII)-(1).216aA-1 to (ZVII)-(1).216aA-514;
compounds (ZVIII)-(1).216aA-1 to (ZVIII)-(1).216aA-514;
compounds (ZIX)-(1).216aA-1 to (ZIX)-(1).216aA-514;
compounds (ZX)-(1).216aA-1 to (ZX)-(1).216aA-514;
compounds (ZXI)-(1).216aA-1 to (ZXI)-(1).216aA-514;
compounds (ZXII)-(1).216aA-1 to (ZXII)-(1).216aA-514)
table 217a
Compounds (Z)-(1), wherein A is 2-chloro-4-(trifluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).217aA-1 to (ZI)-(1).217aA-514; compounds (ZII)-(1).217aA-1 to (ZII)-(1).217aA-514;
compounds (ZIII)-(1).217aA-1 to (ZIII)-(1).217aA-514;
compounds (ZIV)-(1).217aA-1 to (ZIV)-(1).217aA-514;
compounds (ZV)-(1).217aA-1 to (ZV)-(1).217aA-514;
compounds (ZVI)-(1).217aA-1 to (ZVI)-(1).217aA-514;
compounds (ZVII)-(1).217aA-1 to (ZVII)-(1).217aA-514;
compounds (ZVIII)-(1).217aA-1 to (ZVIII)-(1).217aA-514;
compounds (ZIX)-(1).217aA-1 to (ZIX)-(1).217aA-514;
compounds (ZX)-(1).217aA-1 to (ZX)-(1).217aA-514;
compounds (ZXI)-(1).217aA-1 to (ZXI)-(1).217aA-514;
compounds (ZXII)-(1).217aA-1 to (ZXII)-(1).217aA-514)
table 218a
Compounds (Z)-(1), wherein A is 2-chloro-5-(trifluoromethoxy)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).218aA-1 to (ZI)-(1).218aA-514; compounds (ZII)-(1).218aA-1 to (ZII)-(1).218aA-514;
compounds (ZIII)-(1).218aA-1 to (ZIII)-(1).218aA-514;
compounds (ZIV)-(1).218aA-1 to (ZIV)-(1).218aA-514;
compounds (ZV)-(1).218aA-1 to (ZV)-(1).218aA-514;
compounds (ZVI)-(1).218aA-1 to (ZVI)-(1).218aA-514;
compounds (ZVII)-(1).218aA-1 to (ZVII)-(1).218aA-514;
compounds (ZVIII)-(1).218aA-1 to (ZVIII)-(1).218aA-514;
compounds (ZIX)-(1).218aA-1 to (ZIX)-(1).218aA-514;
compounds (ZX)-(1 ).218aA-1 to (ZX)-(1 ).218aA-514;
compounds (ZXI)-(1).218aA-1 to (ZXI)-(1).218aA-514;
compounds (ZXII)-(1).218aA-1 to (ZXII)-(1).218aA-514)
table 219a
Compounds (Z)-(1), wherein A is 3-chloro-4-(trifluoromethoxy)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).219aA-1 to (ZI)-(1).219aA-514; compounds (ZII)-(1).219aA-1 to (ZII)-(1).219aA-514;
compounds (ZIII)-(1).219aA-1 to (ZIII)-(1).219aA-514;
compounds (ZIV)-(1).219aA-1 to (ZIV)-(1).219aA-514;
compounds (ZV)-(1).219aA-1 to (ZV)-(1).219aA-514;
compounds (ZVI)-(1).219aA-1 to (ZVI)-(1).219aA-514;
compounds (ZVII)-(1).219aA-1 to (ZVII)-(1).219aA-514;
compounds (ZVIII)-(1).219aA-1 to (ZVIII)-(1).219aA-514;
compounds (ZIX)-(1).219aA-1 to (ZIX)-(1).219aA-514;
compounds (ZX)-(1).219aA-1 to (ZX)-(1).219aA-514;
compounds (ZXI)-(1).219aA-1 to (ZXI)-(1).219aA-514;
compounds (ZXII)-(1).219aA-1 to (ZXII)-(1).219aA-514)
table 220a
Compounds (Z)-(1), wherein A is 2-(difluoromethoxy)-3-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).220aA-1 to (ZI)-(1).220aA-514; compounds (ZII)-(1).220aA-1 to (ZII)-(1).220aA-514;
compounds (ZIII)-(1).220aA-1 to (ZIII)-(1).220aA-514;
compounds (ZIV)-(1).220aA-1 to (ZIV)-(1).220aA-514;
compounds (ZV)-(1).220aA-1 to (ZV)-(1).220aA-514;
compounds (ZVI)-(1).220aA-1 to (ZVI)-(1).220aA-514;
compounds (ZVII)-(1).220aA-1 to (ZVII)-(1).220aA-514;
compounds (ZVIII)-(1).220aA-1 to (ZVIII)-(1).220aA-514;
compounds (ZIX)-(1).220aA-1 to (ZIX)-(1).220aA-514;
compounds (ZX)-(1).220aA-1 to (ZX)-(1).220aA-514;
compounds (ZXI)-(1).220aA-1 to (ZXI)-(1).220aA-514;
compounds (ZXII)-(1).220aA-1 to (ZXII)-(1).220aA-514)
table 221a
Compounds (Z)-(1), wherein A is 2-(difluoromethoxy)-4-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).221aA-1 to (ZI)-(1).221aA-514; compounds (ZII)-(1).221aA-1 to (ZII)-(1).221aA-514;
compounds (ZIII)-(1).221aA-1 to (ZIII)-(1).221aA-514;
compounds (ZIV)-(1).221aA-1 to (ZIV)-(1).221aA-514;
compounds (ZV)-(1).221aA-1 to (ZV)-(1).221aA-514;
compounds (ZVI)-(1).221aA-1 to (ZVI)-(1).221aA-514;
compounds (ZVII)-(1).221aA-1 to (ZVII)-(1).221aA-514;
compounds (ZVIII)-(1).221aA-1 to (ZVIII)-(1).221aA-514;
compounds (ZIX)-(1).221aA-1 to (ZIX)-(1).221aA-514;
compounds (ZX)-(1).221aA-1 to (ZX)-(1).221aA-514;
compounds (ZXI)-(1).221aA-1 to (ZXI)-(1).221aA-514;
compounds (ZXII)-(1).221aA-1 to (ZXII)-(1).221aA-514)
table 222a
Compounds (Z)-(1), wherein A is 2-(difluoromethoxy)-5-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).222aA-1 to (ZI)-(1).222aA-514; compounds (ZII)-(1).222aA-1 to (ZII)-(1).222aA-514;
compounds (ZIII)-(1).222aA-1 to (ZIII)-(1).222aA-514;
compounds (ZIV)-(1).222aA-1 to (ZIV)-(1).222aA-514;
compounds (ZV)-(1).222aA-1 to (ZV)-(1).222aA-514;
compounds (ZVI)-(1).222aA-1 to (ZVI)-(1).222aA-514;
compounds (ZVII)-(1).222aA-1 to (ZVII)-(1).222aA-514;
compounds (ZVIII)-(1).222aA-1 to (ZVIII)-(1).222aA-514;
compounds (ZIX)-(1).222aA-1 to (ZIX)-(1).222aA-514;
compounds (ZX)-(1).222aA-1 to (ZX)-(1).222aA-514;
compounds (ZXI)-(1).222aA-1 to (ZXI)-(1).222aA-514;
compounds (ZXII)-(1).222aA-1 to (ZXII)-(1).222aA-514)
table 223a
Compounds (Z)-(1), wherein A is 2-(difluoromethoxy)-6-chlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).223aA-1 to (ZI)-(1).223aA-514; compounds (ZII)-(1).223aA-1 to (ZII)-(1).223aA-514;
compounds (ZIII)-(1).223aA-1 to (ZIII)-(1).223aA-514;
compounds (ZIV)-(1).223aA-1 to (ZIV)-(1).223aA-514;
compounds (ZV)-(1).223aA-1 to (ZV)-(1).223aA-514;
compounds (ZVI)-(1).223aA-1 to (ZVI)-(1).223aA-514;
compounds (ZVII)-(1).223aA-1 to (ZVII)-(1).223aA-514;
compounds (ZVIII)-(1).223aA-1 to (ZVIII)-(1).223aA-514;
compounds (ZIX)-(1).223aA-1 to (ZIX)-(1).223aA-514;
compounds (ZX)-(1).223aA-1 to (ZX)-(1).223aA-514;
compounds (ZXI)-(1).223aA-1 to (ZXI)-(1).223aA-514;
compounds (ZXII)-(1).223aA-1 to (ZXII)-(1).223aA-514)
table 224a
Compounds (Z)-(1), wherein A is 3-(difluoromethoxy)-4-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).224aA-1 to (ZI)-(1).224aA-514; compounds (ZII)-(1).224aA-1 to (ZII)-(1).224aA-514;
compounds (ZIII)-(1).224aA-1 to (ZIII)-(1).224aA-514;
compounds (ZIV)-(1).224aA-1 to (ZIV)-(1).224aA-514;
compounds (ZV)-(1 ).224aA-1 to (ZV)-(1 ).224aA-514;
compounds (ZVI)-(1).224aA-1 to (ZVI)-(1).224aA-514;
compounds (ZVII)-(1).224aA-1 to (ZVII)-(1).224aA-514;
compounds (ZVIII)-(1).224aA-1 to (ZVIII)-(1).224aA-514;
compounds (ZIX)-(1).224aA-1 to (ZIX)-(1).224aA-514;
compounds (ZX)-(1 ).224aA-1 to (ZX)-(1 ).224aA-514;
compounds (ZXI)-(1).224aA-1 to (ZXI)-(1).224aA-514;
compounds (ZXII)-(1).224aA-1 to (ZXII)-(1).224aA-514)
table 225a
Compounds (Z)-(1), wherein A is 3-(difluoromethoxy)-5-chlorophenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).225aA-1 to (ZI)-(1).225aA-514; compounds (ZII)-(1).225aA-1 to (ZII)-(1).225aA-514;
compounds (ZIII)-(1).225aA-1 to (ZIII)-(1).225aA-514;
compounds (ZIV)-(1).225aA-1 to (ZIV)-(1).225aA-514;
compounds (ZV)-(1).225aA-1 to (ZV)-(1).225aA-514;
compounds (ZVI)-(1).225aA-1 to (ZVI)-(1).225aA-514;
compounds (ZVII)-(1).225aA-1 to (ZVII)-(1).225aA-514;
compounds (ZVIII)-(1).225aA-1 to (ZVIII)-(1).225aA-514;
compounds (ZIX)-(1).225aA-1 to (ZIX)-(1).225aA-514;
compounds (ZX)-(1).225aA-1 to (ZX)-(1).225aA-514;
compounds (ZXI)-(1).225aA-1 to (ZXI)-(1).225aA-514;
compounds (ZXII)-(1).225aA-1 to (ZXII)-(1).225aA-514)
table 226a
Compounds (Z)-(1), wherein A is 2-chloro-3-(difluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).226aA-1 to (ZI)-(1).226aA-514; compounds (ZII)-(1).226aA-1 to (ZII)-(1).226aA-514;
compounds (ZIII)-(1).226aA-1 to (ZIII)-(1).226aA-514;
compounds (ZIV)-(1).226aA-1 to (ZIV)-(1).226aA-514;
compounds (ZV)-(1).226aA-1 to (ZV)-(1).226aA-514;
compounds (ZVI)-(1).226aA-1 to (ZVI)-(1).226aA-514;
compounds (ZVII)-(1).226aA-1 to (ZVII)-(1).226aA-514;
compounds (ZVIII)-(1).226aA-1 to (ZVIII)-(1).226aA-514;
compounds (ZIX)-(1).226aA-1 to (ZIX)-(1).226aA-514;
compounds (ZX)-(1).226aA-1 to (ZX)-(1).226aA-514;
compounds (ZXI)-(1).226aA-1 to (ZXI)-(1).226aA-514;
compounds (ZXII)-(1).226aA-1 to (ZXII)-(1).226aA-514)
table 227a
Compounds (Z)-(1), wherein A is 2-chloro-4-(difluoromethoxy)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).227aA-1 to (ZI)-(1).227aA-514; compounds (ZII)-(1).227aA-1 to (ZII)-(1).227aA-514;
compounds (ZIII)-(1).227aA-1 to (ZIII)-(1).227aA-514;
compounds (ZIV)-(1).227aA-1 to (ZIV)-(1).227aA-514;
compounds (ZV)-(1 ).227aA-1 to (ZV)-(1 ).227aA-514;
compounds (ZVI)-(1).227aA-1 to (ZVI)-(1).227aA-514;
compounds (ZVII)-(1).227aA-1 to (ZVII)-(1).227aA-514;
compounds (ZVIII)-(1).227aA-1 to (ZVIII)-(1).227aA-514;
compounds (ZIX)-(1).227aA-1 to (ZIX)-(1).227aA-514;
compounds (ZX)-(1 ).227aA-1 to (ZX)-(1 ).227aA-514;
compounds (ZXI)-(1).227aA-1 to (ZXI)-(1).227aA-514;
compounds (ZXII)-(1).227aA-1 to (ZXII)-(1).227aA-514)
table 228a
Compounds (Z)-(1), wherein A is 2-chloro-5-(difluoromethoxy)phenyl and B corre- sponds to one row of table A (compounds (ZI)-(1).228aA-1 to (ZI)-(1).228aA-514; compounds (ZII)-(1).228aA-1 to (ZII)-(1).228aA-514;
compounds (ZIII)-(1).228aA-1 to (ZIII)-(1).228aA-514;
compounds (ZIV)-(1).228aA-1 to (ZIV)-(1).228aA-514;
compounds (ZV)-(1).228aA-1 to (ZV)-(1).228aA-514;
compounds (ZVI)-(1).228aA-1 to (ZVI)-(1).228aA-514;
compounds (ZVII)-(1).228aA-1 to (ZVII)-(1).228aA-514;
compounds (ZVIII)-(1).228aA-1 to (ZVIII)-(1).228aA-514;
compounds (ZIX)-(1).228aA-1 to (ZIX)-(1).228aA-514;
compounds (ZX)-(1).228aA-1 to (ZX)-(1).228aA-514;
compounds (ZXI)-(1).228aA-1 to (ZXI)-(1).228aA-514;
compounds (ZXII)-(1).228aA-1 to (ZXII)-(1).228aA-514)
table 229a
Compounds (Z)-(1), wherein A is 3-chloro-4-(difluoromethoxy)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).229aA-1 to (ZI)-(1).229aA-514; compounds (ZII)-(1).229aA-1 to (ZII)-(1).229aA-514;
compounds (ZIII)-(1).229aA-1 to (ZIII)-(1).229aA-514;
compounds (ZIV)-(1).229aA-1 to (ZIV)-(1).229aA-514;
compounds (ZV)-(1).229aA-1 to (ZV)-(1).229aA-514;
compounds (ZVI)-(1).229aA-1 to (ZVI)-(1).229aA-514;
compounds (ZVII)-(1).229aA-1 to (ZVII)-(1).229aA-514;
compounds (ZVIII)-(1).229aA-1 to (ZVIII)-(1).229aA-514;
compounds (ZIX)-(1).229aA-1 to (ZIX)-(1).229aA-514;
compounds (ZX)-(1).229aA-1 to (ZX)-(1).229aA-514;
compounds (ZXI)-(1).229aA-1 to (ZXI)-(1).229aA-514;
compounds (ZXII)-(1).229aA-1 to (ZXII)-(1).229aA-514)
table 230a
Compounds (Z)-(1), wherein A is 2-(trifluoromethylthio)-3-chlorophenyl and B cor- responds to one row of table A (compounds (ZI)-(1).230aA-1 to (ZI)-(1).230aA-514; compounds (ZII)-(1).230aA-1 to (ZII)-(1).230aA-514;
compounds (ZIII)-(1).230aA-1 to (ZIII)-(1).230aA-514;
compounds (ZIV)-(1).230aA-1 to (ZIV)-(1).230aA-514;
compounds (ZV)-(1 ).230aA-1 to (ZV)-(1 ).230aA-514;
compounds (ZVI)-(1).230aA-1 to (ZVI)-(1).230aA-514;
compounds (ZVII)-(1).230aA-1 to (ZVII)-(1).230aA-514;
compounds (ZVIII)-(1).230aA-1 to (ZVIII)-(1).230aA-514;
compounds (ZIX)-(1).230aA-1 to (ZIX)-(1).230aA-514;
compounds (ZX)-(1 ).230aA-1 to (ZX)-(1 ).230aA-514;
compounds (ZXI)-(1).230aA-1 to (ZXI)-(1).230aA-514;
compounds (ZXII)-(1).230aA-1 to (ZXII)-(1).230aA-514)
table 231a
Compounds (Z)-(1), wherein A is 2-(trifluoromethylthio)-4-chlorophenyl and B cor- responds to one row of table A (compounds (ZI)-(1).231aA-1 to (ZI)-(1).231aA-514; compounds (ZII)-(1).231aA-1 to (ZII)-(1).231aA-514;
compounds (ZIII)-(1).231aA-1 to (Zll l)-(1 ).231 aA-514;
compounds (ZIV)-(1).231aA-1 to (ZIV)-(1).231aA-514;
compounds (ZV)-(1).231aA-1 to (ZV)-(1).231aA-514;
compounds (ZVI)-(1).231aA-1 to (ZVI)-(1).231aA-514;
compounds (ZVII)-(1).231aA-1 to (ZVII)-(1).231aA-514;
compounds (ZVIII)-(1).231aA-1 to (ZVIII)-(1).231aA-514;
compounds (ZIX)-(1).231aA-1 to (ZIX)-(1).231aA-514;
compounds (ZX)-(1).231aA-1 to (ZX)-(1).231aA-514;
compounds (ZXI)-(1).231aA-1 to (ZXI)-(1).231aA-514;
compounds (ZXII)-(1).231aA-1 to (ZXII)-(1).231aA-514)
table 232a
Compounds (Z)-(1), wherein A is 2-(trifluoromethylthio)-5-chlorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).232aA-1 to (Zl)-(1 ).232aA-514; compounds (ZII)-(1).232aA-1 to (ZII)-(1).232aA-514;
compounds (ZIII)-(1).232aA-1 to (ZIII)-(1).232aA-514;
compounds (ZIV)-(1).232aA-1 to (ZIV)-(1).232aA-514;
compounds (ZV)-(1).232aA-1 to (ZV)-(1).232aA-514;
compounds (ZVI)-(1).232aA-1 to (ZVI)-(1).232aA-514;
compounds (ZVII)-(1).232aA-1 to (ZVII)-(1).232aA-514;
compounds (ZVIII)-(1).232aA-1 to (ZVIII)-(1).232aA-514;
compounds (ZIX)-(1).232aA-1 to (ZIX)-(1).232aA-514;
compounds (ZX)-(1).232aA-1 to (ZX)-(1).232aA-514;
compounds (ZXI)-(1).232aA-1 to (ZXI)-(1).232aA-514;
compounds (ZXII)-(1).232aA-1 to (ZXII)-(1).232aA-514)
table 233a
Compounds (Z)-(1), wherein A is 2-(trifluoromethylthio)-6-chlorophenyl and B cor- responds to one row of table A (compounds (Zl)-(1 ).233aA-1 to (Zl)-(1 ).233aA-514; compounds (ZII)-(1).233aA-1 to (ZII)-(1).233aA-514;
compounds (ZIII)-(1).233aA-1 to (ZIII)-(1).233aA-514;
compounds (ZIV)-(1).233aA-1 to (ZIV)-(1).233aA-514;
compounds (ZV)-(1 ).233aA-1 to (ZV)-(1 ).233aA-514;
compounds (ZVI)-(1).233aA-1 to (ZVI)-(1).233aA-514;
compounds (ZVII)-(1).233aA-1 to (ZVII)-(1).233aA-514;
compounds (ZVIII)-(1).233aA-1 to (ZVIII)-(1).233aA-514;
compounds (ZIX)-(1).233aA-1 to (ZIX)-(1).233aA-514;
compounds (ZX)-(1).233aA-1 to (ZX)-(1).233aA-514;
compounds (ZXI)-(1).233aA-1 to (ZXI)-(1).233aA-514;
compounds (ZXII)-(1).233aA-1 to (ZXII)-(1).233aA-514)
table 234a
Compounds (Z)-(1), wherein A is 3-(trifluoromethylthio)-4-chlorophenyl and B cor- responds to one row of table A (compounds (Zl)-(1 ).234aA-1 to (Zl)-(1 ).234aA-514; compounds (ZII)-(1).234aA-1 to (ZII)-(1).234aA-514;
compounds (ZIII)-(1).234aA-1 to (ZIII)-(1).234aA-514;
compounds (ZIV)-(1).234aA-1 to (ZIV)-(1).234aA-514;
compounds (ZV)-(1).234aA-1 to (ZV)-(1).234aA-514;
compounds (ZVI)-(1).234aA-1 to (ZVI)-(1).234aA-514;
compounds (ZVII)-(1).234aA-1 to (ZVII)-(1).234aA-514;
compounds (ZVIII)-(1).234aA-1 to (ZVIII)-(1).234aA-514;
compounds (ZIX)-(1).234aA-1 to (ZIX)-(1).234aA-514;
compounds (ZX)-(1).234aA-1 to (ZX)-(1).234aA-514;
compounds (ZXI)-(1).234aA-1 to (ZXI)-(1).234aA-514;
compounds (ZXII)-(1).234aA-1 to (ZXII)-(1).234aA-514)
table 235a
Compounds (Z)-(1), wherein A is 3-(trifluoromethylthio)-5-chlorophenyl and B corresponds to one row of table A (compounds (Zl)-(1 ).235aA-1 to (Zl)-(1 ).235aA-514; compounds (ZII)-(1).235aA-1 to (ZII)-(1).235aA-514;
compounds (ZIII)-(1).235aA-1 to (ZIII)-(1).235aA-514;
compounds (ZIV)-(1).235aA-1 to (ZIV)-(1).235aA-514;
compounds (ZV)-(1).235aA-1 to (ZV)-(1).235aA-514;
compounds (ZVI)-(1).235aA-1 to (ZVI)-(1).235aA-514;
compounds (ZVII)-(1).235aA-1 to (ZVII)-(1).235aA-514;
compounds (ZVIII)-(1).235aA-1 to (ZVIII)-(1).235aA-514;
compounds (ZIX)-(1).235aA-1 to (ZIX)-(1).235aA-514;
compounds (ZX)-(1).235aA-1 to (ZX)-(1).235aA-514;
compounds (ZXI)-(1).235aA-1 to (ZXI)-(1).235aA-514;
compounds (ZXII)-(1).235aA-1 to (ZXII)-(1).235aA-514)
table 236a
Compounds (Z)-(1), wherein A is 2-chloro-3-(trifluoromethylthio)phenyl and B cor- responds to one row of table A (compounds (ZI)-(1).236aA-1 to (ZI)-(1).236aA-514; compounds (ZII)-(1).236aA-1 to (ZII)-(1).236aA-514;
compounds (ZIII)-(1).236aA-1 to (ZIII)-(1).236aA-514;
compounds (ZIV)-(1).236aA-1 to (ZIV)-(1).236aA-514;
compounds (ZV)-(1 ).236aA-1 to (ZV)-(1 ).236aA-514;
compounds (ZVI)-(1).236aA-1 to (ZVI)-(1).236aA-514;
compounds (ZVII)-(1).236aA-1 to (ZVII)-(1).236aA-514;
compounds (ZVIII)-(1).236aA-1 to (ZVIII)-(1).236aA-514;
compounds (ZIX)-(1).236aA-1 to (ZIX)-(1).236aA-514;
compounds (ZX)-(1 ).236aA-1 to (ZX)-(1 ).236aA-514;
compounds (ZXI)-(1).236aA-1 to (ZXI)-(1).236aA-514;
compounds (ZXII)-(1).236aA-1 to (ZXII)-(1).236aA-514)
table 237a
Compounds (Z)-(1), wherein A is 2-chloro-4-(trifluoromethylthio)phenyl and B cor- responds to one row of table A (compounds (ZI)-(1).237aA-1 to (ZI)-(1).237aA-514; compounds (ZII)-(1).237aA-1 to (ZII)-(1).237aA-514;
compounds (ZIII)-(1).237aA-1 to (ZIII)-(1).237aA-514;
compounds (ZIV)-(1).237aA-1 to (ZIV)-(1).237aA-514;
compounds (ZV)-(1).237aA-1 to (ZV)-(1).237aA-514;
compounds (ZVI)-(1).237aA-1 to (ZVI)-(1).237aA-514;
compounds (ZVII)-(1).237aA-1 to (ZVII)-(1).237aA-514;
compounds (ZVIII)-(1).237aA-1 to (ZVIII)-(1).237aA-514;
compounds (ZIX)-(1).237aA-1 to (ZIX)-(1).237aA-514;
compounds (ZX)-(1).237aA-1 to (ZX)-(1).237aA-514;
compounds (ZXI)-(1).237aA-1 to (ZXI)-(1).237aA-514;
compounds (ZXII)-(1).237aA-1 to (ZXII)-(1).237aA-514)
table 238a
Compounds (Z)-(1), wherein A is 2-chloro-5-(trifluoromethylthio)phenyl and B corresponds to one row of table A (compounds (ZI)-(1).238aA-1 to (ZI)-(1).238aA-514; compounds (ZII)-(1).238aA-1 to (ZII)-(1).238aA-514;
compounds (ZIII)-(1).238aA-1 to (ZIII)-(1).238aA-514;
compounds (ZIV)-(1).238aA-1 to (ZIV)-(1).238aA-514;
compounds (ZV)-(1).238aA-1 to (ZV)-(1).238aA-514;
compounds (ZVI)-(1).238aA-1 to (ZVI)-(1).238aA-514;
compounds (ZVII)-(1).238aA-1 to (ZVII)-(1).238aA-514;
compounds (ZVIII)-(1).238aA-1 to (ZVIII)-(1).238aA-514;
compounds (ZIX)-(1).238aA-1 to (ZIX)-(1).238aA-514;
compounds (ZX)-(1).238aA-1 to (ZX)-(1).238aA-514;
compounds (ZXI)-(1).238aA-1 to (ZXI)-(1).238aA-514;
compounds (ZXII)-(1).238aA-1 to (ZXII)-(1).238aA-514)
table 239a
Compounds (Z)-(1), wherein A is 3-chloro-4-(trifluoromethylthio)phenyl and B cor- responds to one row of table A (compounds (Zl)-(1 ).239aA-1 to (Zl)-(1 ).239aA-514; compounds (ZII)-(1).239aA-1 to (ZII)-(1).239aA-514;
compounds (ZIII)-(1).239aA-1 to (ZIII)-(1).239aA-514;
compounds (ZIV)-(1).239aA-1 to (ZIV)-(1).239aA-514;
compounds (ZV)-(1 ).239aA-1 to (ZV)-(1 ).239aA-514;
compounds (ZVI)-(1).239aA-1 to (ZVI)-(1).239aA-514;
compounds (ZVII)-(1).239aA-1 to (ZVII)-(1).239aA-514;
compounds (ZVIII)-(1).239aA-1 to (ZVIII)-(1).239aA-514;
compounds (ZIX)-(1).239aA-1 to (ZIX)-(1).239aA-514;
compounds (ZX)-(1 ).239aA-1 to (ZX)-(1 ).239aA-514;
compounds (ZXI)-(1).239aA-1 to (ZXI)-(1).239aA-514;
compounds (ZXII)-(1).239aA-1 to (ZXII)-(1).239aA-514)
table 240a
Compounds (Z)-(1), wherein A is 2,3,4-trichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).240aA-1 to (ZI)-(1).240aA-514;
compounds (ZII)-(1).240aA-1 to (ZII)-(1).240aA-514;
compounds (ZIII)-(1).240aA-1 to (ZIII)-(1).240aA-514;
compounds (ZIV)-(1).240aA-1 to (ZIV)-(1).240aA-514;
compounds (ZV)-(1).240aA-1 to (ZV)-(1).240aA-514;
compounds (ZVI)-(1).240aA-1 to (ZVI)-(1).240aA-514;
compounds (ZVII)-(1).240aA-1 to (ZVII)-(1).240aA-514;
compounds (ZVIII)-(1).240aA-1 to (ZVIII)-(1).240aA-514;
compounds (ZIX)-(1).240aA-1 to (ZIX)-(1).240aA-514;
compounds (ZX)-(1).240aA-1 to (ZX)-(1).240aA-514;
compounds (ZXI)-(1).240aA-1 to (ZXI)-(1).240aA-514;
compounds (ZXII)-(1).240aA-1 to (ZXII)-(1).240aA-514)
table 241a
Compounds (Z)-(1), wherein A is 2,3,5-trichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).241aA-1 to (ZI)-(1).241aA-514;
compounds (ZII)-(1).241aA-1 to (ZII)-(1).241aA-514;
compounds (ZIII)-(1).241aA-1 to (Zll l)-(1 ).241 aA-514;
compounds (ZIV)-(1).241aA-1 to (ZIV)-(1).241aA-514;
compounds (ZV)-(1).241aA-1 to (ZV)-(1).241aA-514;
compounds (ZVI)-(1).241aA-1 to (ZVI)-(1).241aA-514;
compounds (ZVII)-(1).241aA-1 to (ZVII)-(1).241aA-514;
compounds (ZVIII)-(1).241aA-1 to (ZVIII)-(1).241aA-514;
compounds (ZIX)-(1).241aA-1 to (ZIX)-(1).241aA-514;
compounds (ZX)-(1).241aA-1 to (ZX)-(1).241aA-514;
compounds (ZXI)-(1).241aA-1 to (ZXI)-(1).241aA-514;
compounds (ZXII)-(1).241aA-1 to (ZXII)-(1).241aA-514)
table 242a
Compounds (Z)-(1), wherein A is 2,3,6-trichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).242aA-1 to (ZI)-(1).242aA-514;
compounds (ZII)-(1).242aA-1 to (ZII)-(1).242aA-514;
compounds (ZIII)-(1).242aA-1 to (ZIII)-(1).242aA-514;
compounds (ZIV)-(1).242aA-1 to (ZIV)-(1).242aA-514;
compounds (ZV)-(1 ).242aA-1 to (ZV)-(1 ).242aA-514;
compounds (ZVI)-(1).242aA-1 to (ZVI)-(1).242aA-514;
compounds (ZVII)-(1).242aA-1 to (ZVII)-(1).242aA-514;
compounds (ZVIII)-(1).242aA-1 to (ZVIII)-(1).242aA-514;
compounds (ZIX)-(1).242aA-1 to (ZIX)-(1).242aA-514;
compounds (ZX)-(1 ).242aA-1 to (ZX)-(1 ).242aA-514;
compounds (ZXI)-(1).242aA-1 to (ZXI)-(1).242aA-514;
compounds (ZXII)-(1).242aA-1 to (ZXII)-(1).242aA-514)
table 243a
Compounds (Z)-(1), wherein A is 2,4,5-trichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).243aA-1 to (ZI)-(1).243aA-514;
compounds (ZII)-(1).243aA-1 to (ZII)-(1).243aA-514;
compounds (ZIII)-(1).243aA-1 to (ZIII)-(1).243aA-514;
compounds (ZIV)-(1).243aA-1 to (ZIV)-(1).243aA-514;
compounds (ZV)-(1).243aA-1 to (ZV)-(1).243aA-514;
compounds (ZVI)-(1).243aA-1 to (ZVI)-(1).243aA-514;
compounds (ZVII)-(1).243aA-1 to (ZVII)-(1).243aA-514;
compounds (ZVIII)-(1).243aA-1 to (ZVIII)-(1).243aA-514;
compounds (ZIX)-(1).243aA-1 to (ZIX)-(1).243aA-514;
compounds (ZX)-(1).243aA-1 to (ZX)-(1).243aA-514;
compounds (ZXI)-(1).243aA-1 to (ZXI)-(1).243aA-514;
compounds (ZXII)-(1).243aA-1 to (ZXII)-(1).243aA-514)
table 244a
Compounds (Z)-(1), wherein A is 2,4,6-trichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).244aA-1 to (ZI)-(1).244aA-514;
compounds (ZII)-(1).244aA-1 to (ZII)-(1).244aA-514;
compounds (ZIII)-(1).244aA-1 to (ZIII)-(1).244aA-514;
compounds (ZIV)-(1).244aA-1 to (ZIV)-(1).244aA-514;
compounds (ZV)-(1).244aA-1 to (ZV)-(1).244aA-514;
compounds (ZVI)-(1).244aA-1 to (ZVI)-(1).244aA-514;
compounds (ZVII)-(1).244aA-1 to (ZVII)-(1).244aA-514;
compounds (ZVIII)-(1).244aA-1 to (ZVIII)-(1).244aA-514;
compounds (ZIX)-(1).244aA-1 to (ZIX)-(1).244aA-514;
compounds (ZX)-(1).244aA-1 to (ZX)-(1).244aA-514;
compounds (ZXI)-(1).244aA-1 to (ZXI)-(1).244aA-514;
compounds (ZXII)-(1).244aA-1 to (ZXII)-(1).244aA-514)
table 245a
Compounds (Z)-(1), wherein A is 3,4,5-trichlorophenyl and B corresponds to one row of table A (compounds (ZI)-(1).245aA-1 to (ZI)-(1).245aA-514;
compounds (ZII)-(1).245aA-1 to (ZII)-(1).245aA-514;
compounds (ZIII)-(1).245aA-1 to (ZIII)-(1).245aA-514;
compounds (ZIV)-(1).245aA-1 to (ZIV)-(1).245aA-514;
compounds (ZV)-(1 ).245aA-1 to (ZV)-(1 ).245aA-514;
compounds (ZVI)-(1).245aA-1 to (ZVI)-(1).245aA-514;
compounds (ZVII)-(1).245aA-1 to (ZVII)-(1).245aA-514;
compounds (ZVIII)-(1).245aA-1 to (ZVIII)-(1).245aA-514;
compounds (ZIX)-(1).245aA-1 to (ZIX)-(1).245aA-514;
compounds (ZX)-(1 ).245aA-1 to (ZX)-(1 ).245aA-514;
compounds (ZXI)-(1).245aA-1 to (ZXI)-(1).245aA-514;
compounds (ZXII)-(1).245aA-1 to (ZXII)-(1).245aA-514)
table 246a
Compounds (Z)-(1), wherein A is 2,3,4-trimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).246aA-1 to (ZI)-(1).246aA-514;
compounds (ZII)-(1).246aA-1 to (ZII)-(1).246aA-514;
compounds (ZIII)-(1).246aA-1 to (ZIII)-(1).246aA-514;
compounds (ZIV)-(1).246aA-1 to (ZIV)-(1).246aA-514;
compounds (ZV)-(1).246aA-1 to (ZV)-(1).246aA-514;
compounds (ZVI)-(1).246aA-1 to (ZVI)-(1).246aA-514;
compounds (ZVII)-(1).246aA-1 to (ZVII)-(1).246aA-514;
compounds (ZVIII)-(1).246aA-1 to (ZVIII)-(1).246aA-514;
compounds (ZIX)-(1).246aA-1 to (ZIX)-(1).246aA-514;
compounds (ZX)-(1).246aA-1 to (ZX)-(1).246aA-514;
compounds (ZXI)-(1).246aA-1 to (ZXI)-(1).246aA-514;
compounds (ZXII)-(1).246aA-1 to (ZXII)-(1).246aA-514)
table 247a
Compounds (Z)-(1), wherein A is 2,3,5-trimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).247aA-1 to (ZI)-(1).247aA-514;
compounds (ZII)-(1).247aA-1 to (ZII)-(1).247aA-514;
compounds (ZIII)-(1).247aA-1 to (ZIII)-(1).247aA-514;
compounds (ZIV)-(1).247aA-1 to (ZIV)-(1).247aA-514;
compounds (ZV)-(1).247aA-1 to (ZV)-(1).247aA-514;
compounds (ZVI)-(1).247aA-1 to (ZVI)-(1).247aA-514;
compounds (ZVII)-(1).247aA-1 to (ZVII)-(1).247aA-514;
compounds (ZVIII)-(1).247aA-1 to (ZVIII)-(1).247aA-514;
compounds (ZIX)-(1).247aA-1 to (ZIX)-(1).247aA-514;
compounds (ZX)-(1).247aA-1 to (ZX)-(1).247aA-514;
compounds (ZXI)-(1).247aA-1 to (ZXI)-(1).247aA-514;
compounds (ZXII)-(1).247aA-1 to (ZXII)-(1).247aA-514)
table 248a
Compounds (Z)-(1), wherein A is 2,3,6-trimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).248aA-1 to (ZI)-(1).248aA-514;
compounds (ZII)-(1).248aA-1 to (ZII)-(1).248aA-514;
compounds (ZIII)-(1).248aA-1 to (ZIII)-(1).248aA-514;
compounds (ZIV)-(1).248aA-1 to (ZIV)-(1).248aA-514;
compounds (ZV)-(1 ).248aA-1 to (ZV)-(1 ).248aA-514;
compounds (ZVI)-(1).248aA-1 to (ZVI)-(1).248aA-514;
compounds (ZVII)-(1).248aA-1 to (ZVII)-(1).248aA-514;
compounds (ZVIII)-(1).248aA-1 to (ZVIII)-(1).248aA-514;
compounds (ZIX)-(1).248aA-1 to (ZIX)-(1).248aA-514;
compounds (ZX)-(1 ).248aA-1 to (ZX)-(1 ).248aA-514;
compounds (ZXI)-(1).248aA-1 to (ZXI)-(1).248aA-514;
compounds (ZXII)-(1).248aA-1 to (ZXII)-(1).248aA-514)
table 249a
Compounds (Z)-(1), wherein A is 2,4,5-trimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).249aA-1 to (ZI)-(1).249aA-514;
compounds (ZII)-(1).249aA-1 to (ZII)-(1).249aA-514;
compounds (ZIII)-(1).249aA-1 to (ZIII)-(1).249aA-514;
compounds (ZIV)-(1).249aA-1 to (ZIV)-(1).249aA-514;
compounds (ZV)-(1).249aA-1 to (ZV)-(1).249aA-514;
compounds (ZVI)-(1).249aA-1 to (ZVI)-(1).249aA-514;
compounds (ZVII)-(1).249aA-1 to (ZVII)-(1).249aA-514;
compounds (ZVIII)-(1).249aA-1 to (ZVIII)-(1).249aA-514;
compounds (ZIX)-(1).249aA-1 to (ZIX)-(1).249aA-514;
compounds (ZX)-(1).249aA-1 to (ZX)-(1).249aA-514;
compounds (ZXI)-(1).249aA-1 to (ZXI)-(1).249aA-514;
compounds (ZXII)-(1).249aA-1 to (ZXII)-(1).249aA-514)
table 250a
Compounds (Z)-(1), wherein A is 2,4,6-trimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).250aA-1 to (ZI)-(1).250aA-514;
compounds (ZII)-(1).250aA-1 to (ZII)-(1).250aA-514;
compounds (ZIII)-(1).250aA-1 to (ZIII)-(1).250aA-514;
compounds (ZIV)-(1).250aA-1 to (ZIV)-(1).250aA-514;
compounds (ZV)-(1).250aA-1 to (ZV)-(1).250aA-514;
compounds (ZVI)-(1).250aA-1 to (ZVI)-(1).250aA-514;
compounds (ZVII)-(1).250aA-1 to (ZVII)-(1).250aA-514;
compounds (ZVIII)-(1).250aA-1 to (ZVIII)-(1).250aA-514;
compounds (ZIX)-(1).250aA-1 to (ZIX)-(1).250aA-514;
compounds (ZX)-(1).250aA-1 to (ZX)-(1).250aA-514;
compounds (ZXI)-(1).250aA-1 to (ZXI)-(1).250aA-514;
compounds (ZXII)-(1).250aA-1 to (ZXII)-(1).250aA-514)
table 251a
Compounds (Z)-(1), wherein A is 3,4,5-trimethylphenyl and B corresponds to one row of table A (compounds (ZI)-(1).251aA-1 to (ZI)-(1).251aA-514;
compounds (ZII)-(1).251aA-1 to (ZII)-(1).251aA-514;
compounds (ZIII)-(1).251aA-1 to (ZIII)-(1).251aA-514;
compounds (ZIV)-(1).251aA-1 to (ZIV)-(1).251aA-514;
compounds (ZV)-(1 ).251 aA-1 to (ZV)-(1 ).251 aA-514;
compounds (ZVI)-(1).251aA-1 to (ZVI)-(1).251aA-514;
compounds (ZVII)-(1).251aA-1 to (ZVII)-(1).251aA-514;
compounds (ZVIII)-(1).251aA-1 to (ZVIII)-(1).251aA-514;
compounds (ZIX)-(1).251aA-1 to (ZIX)-(1).251aA-514;
compounds (ZX)-(1 ).251 aA-1 to (ZX)-(1 ).251 aA-514;
compounds (ZXI)-(1).251aA-1 to (ZXI)-(1).251aA-514;
compounds (ZXII)-(1).251aA-1 to (ZXII)-(1).251aA-514)
table 252a
Compounds (Z)-(1), wherein A is 2,3,4-trimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).252aA-1 to (ZI)-(1).252aA-514;
compounds (ZII)-(1).252aA-1 to (ZII)-(1).252aA-514;
compounds (ZIII)-(1).252aA-1 to (ZIII)-(1).252aA-514;
compounds (ZIV)-(1).252aA-1 to (ZIV)-(1).252aA-514;
compounds (ZV)-(1).252aA-1 to (ZV)-(1).252aA-514;
compounds (ZVI)-(1).252aA-1 to (ZVI)-(1).252aA-514;
compounds (ZVII)-(1).252aA-1 to (ZVII)-(1).252aA-514;
compounds (ZVIII)-(1).252aA-1 to (ZVIII)-(1).252aA-514;
compounds (ZIX)-(1).252aA-1 to (ZIX)-(1).252aA-514;
compounds (ZX)-(1).252aA-1 to (ZX)-(1).252aA-514;
compounds (ZXI)-(1).252aA-1 to (ZXI)-(1).252aA-514;
compounds (ZXII)-(1).252aA-1 to (ZXII)-(1).252aA-514)
table 253a
Compounds (Z)-(1), wherein A is 2,3,5-trimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).253aA-1 to (ZI)-(1).253aA-514;
compounds (ZII)-(1).253aA-1 to (ZII)-(1).253aA-514;
compounds (ZIII)-(1).253aA-1 to (ZIII)-(1).253aA-514;
compounds (ZIV)-(1).253aA-1 to (ZIV)-(1).253aA-514;
compounds (ZV)-(1).253aA-1 to (ZV)-(1).253aA-514;
compounds (ZVI)-(1).253aA-1 to (ZVI)-(1).253aA-514;
compounds (ZVII)-(1).253aA-1 to (ZVII)-(1).253aA-514;
compounds (ZVIII)-(1).253aA-1 to (ZVIII)-(1).253aA-514;
compounds (ZIX)-(1).253aA-1 to (ZIX)-(1).253aA-514;
compounds (ZX)-(1).253aA-1 to (ZX)-(1).253aA-514;
compounds (ZXI)-(1).253aA-1 to (ZXI)-(1).253aA-514;
compounds (ZXII)-(1).253aA-1 to (ZXII)-(1).253aA-514)
table 254a
Compounds (Z)-(1), wherein A is 2,3,6-trimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).254aA-1 to (ZI)-(1).254aA-514;
compounds (ZII)-(1).254aA-1 to (ZII)-(1).254aA-514;
compounds (ZIII)-(1).254aA-1 to (ZIII)-(1).254aA-514;
compounds (ZIV)-(1).254aA-1 to (ZIV)-(1).254aA-514;
compounds (ZV)-(1 ).254aA-1 to (ZV)-(1 ).254aA-514;
compounds (ZVI)-(1).254aA-1 to (ZVI)-(1).254aA-514;
compounds (ZVII)-(1).254aA-1 to (ZVII)-(1).254aA-514;
compounds (ZVIII)-(1).254aA-1 to (ZVIII)-(1).254aA-514;
compounds (ZIX)-(1).254aA-1 to (ZIX)-(1).254aA-514;
compounds (ZX)-(1 ).254aA-1 to (ZX)-(1 ).254aA-514;
compounds (ZXI)-(1).254aA-1 to (ZXI)-(1).254aA-514;
compounds (ZXII)-(1).254aA-1 to (ZXII)-(1).254aA-514)
table 255a
Compounds (Z)-(1), wherein A is 2,4,5-trimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).255aA-1 to (ZI)-(1).255aA-514;
compounds (ZII)-(1).255aA-1 to (ZII)-(1).255aA-514;
compounds (ZIII)-(1).255aA-1 to (ZIII)-(1).255aA-514;
compounds (ZIV)-(1).255aA-1 to (ZIV)-(1).255aA-514;
compounds (ZV)-(1).255aA-1 to (ZV)-(1).255aA-514;
compounds (ZVI)-(1).255aA-1 to (ZVI)-(1).255aA-514;
compounds (ZVII)-(1).255aA-1 to (ZVII)-(1).255aA-514;
compounds (ZVIII)-(1).255aA-1 to (ZVIII)-(1).255aA-514;
compounds (ZIX)-(1).255aA-1 to (ZIX)-(1).255aA-514;
compounds (ZX)-(1).255aA-1 to (ZX)-(1).255aA-514;
compounds (ZXI)-(1).255aA-1 to (ZXI)-(1).255aA-514;
compounds (ZXII)-(1).255aA-1 to (ZXII)-(1).255aA-514)
table 256a
Compounds (Z)-(1), wherein A is 2,4,6-trimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1).256aA-1 to (ZI)-(1).256aA-514;
compounds (ZII)-(1).256aA-1 to (ZII)-(1).256aA-514;
compounds (ZIII)-(1).256aA-1 to (ZIII)-(1).256aA-514;
compounds (ZIV)-(1).256aA-1 to (ZIV)-(1).256aA-514;
compounds (ZV)-(1).256aA-1 to (ZV)-(1).256aA-514;
compounds (ZVI)-(1).256aA-1 to (ZVI)-(1).256aA-514;
compounds (ZVII)-(1).256aA-1 to (ZVII)-(1).256aA-514;
compounds (ZVIII)-(1).256aA-1 to (ZVIII)-(1).256aA-514;
compounds (ZIX)-(1).256aA-1 to (ZIX)-(1).256aA-514;
compounds (ZX)-(1).256aA-1 to (ZX)-(1).256aA-514;
compounds (ZXI)-(1).256aA-1 to (ZXI)-(1).256aA-514;
compounds (ZXII)-(1).256aA-1 to (ZXII)-(1).256aA-514)
table 257a
Compounds (Z)-(1), wherein A is 3,4,5-trimethoxyphenyl and B corresponds to one row of table A (compounds (ZI)-(1 ).257aA-1 to (ZI)-(1 ).257aA-514;
compounds (ZII)-(1 ).257aA-1 to (ZII)-(1 ).257aA-514;
compounds (ZIII)-(1 ).257aA-1 to (ZIII)-(1 ).257aA-514;
compounds (ZIV)-(1 ).257aA-1 to (ZIV)-(1 ).257aA-514;
compounds (ZV)-(1 ).257aA-1 to (ZV)-(1 ).257aA-514;
compounds (ZVI)-(1 ).257aA-1 to (ZVI)-(1 ).257aA-514;
compounds (ZVII)-(1 ).257aA-1 to (ZVII)-(1 ).257aA-514;
compounds (ZVIII)-(1 ).257aA-1 to (ZVIII)-(1 ).257aA-514;
compounds (ZIX)-(1 ).257aA-1 to (ZIX)-(1 ).257aA-514;
compounds (ZX)-(1 ).257aA-1 to (ZX)-(1 ).257aA-514;
compounds (ZXI)-(1 ).257aA-1 to (ZXI)-(1 ).257aA-514;
compounds (ZXII)-(1 ).257aA-1 to (ZXII)-(1 ).257aA-514)
table A
row B row B
A-1 phenyl A-28 4-trifluoromethylthiophenyl
A-2 2-chlorophenyl A-29 2,3-dichlorophenyl
A-3 3-chlorophenyl A-30 2,4-dichlorophenyl
A-4 4-chlorophenyl A-31 2,5-dichlorophenyl
A-5 2-fluorophenyl A-32 2,6-dichlorophenyl
A-6 3-fluorophenyl A-33 3,4-dichlorophenyl
A-7 4-fluorophenyl A-34 3,5-dichlorophenyl
A-8 2-methylphenyl A-35 2,3-difluorophenyl
A-9 3-methylphenyl A-36 2,4-difluorophenyl
A-10 4-methylphenyl A-37 2,5-difluorophenyl
A-1 1 2-ethylphenyl A-38 2,6-difluorophenyl
A-12 3-ethylphenyl A-39 3,4-difluorophenyl
A-13 4-ethylphenyl A-40 3,5-difluorophenyl
A-14 2-methoxyphenyl A-41 2,3-dimethylphenyl
A-15 3-methoxyphenyl A-42 2,4-dimethylphenyl
A-16 4-methoxyphenyl A-43 2,5-dimethylphenyl
A-17 2-trifluoromethylphenyl A-44 2,6-dimethylphenyl
A-18 3-trifluoromethylphenyl A-45 3,4-dimethylphenyl
A-19 4-trifluoromethylphenyl A-46 3,5-dimethylphenyl
A-20 2-trifluoromethoxyphenyl A-47 2,3-diethylphenyl
A-21 3-trifluoromethoxyphenyl A-48 2,4-diethylphenyl
A-22 4-trifluoromethoxyphenyl A-49 2,5-diethylphenyl
A-23 2-difluoromethoxyphenyl A-50 2,6-diethylphenyl
A-24 3-difluoromethoxyphenyl A-51 3,5-diethylphenyl
A-25 4-difluoromethoxyphenyl A-52 3,4-diethylphenyl
A-26 2-trifluoromethylthiophenyl A-53 2,3-dimethoxyphenyl
A-27 3-trifluoromethylthiophenyl A-54 2,4-dimethoxyphenyl row B row B
A-55 2,5-dimethoxyphenyl A-89 2-chloro-3-fluorophenyl
A-56 2,6-dimethoxyphenyl A-90 2-chloro-4-fluorophenyl
A-57 3,4-dimethoxyphenyl A-91 2-chloro-5-fluorophenyl
A-58 3,5-dimethoxyphenyl A-92 3-chloro-4-fluorophenyl
A-59 2,3-di(trifluoromethyl)phenyl A-93 2-methyl-3-chlorophenyl
A-60 2,4-di(trifluoromethyl)phenyl A-94 2-methyl-4-chlorophenyl
A-61 2,5-di(trifluoromethyl)phenyl A-95 2-methyl-5-chlorophenyl
A-62 2,6-di(trifluoromethyl)phenyl A-96 2-methyl-6-chlorophenyl
A-63 3,4-di(trifluoromethyl)phenyl A-97 3-methyl-4-chlorophenyl
A-64 3,5-di(trifluoromethyl)phenyl A-98 3-methyl-5-chlorophenyl
A-65 2,3-di(trifluoromethoxy)phenyl A-99 2-chloro-3-methylphenyl
A-66 2,4-di(trifluoromethoxy)phenyl A-100 2-chloro-4-methylphenyl
A-67 2,5-di(trifluoromethoxy)phenyl A-101 2-chloro-5-methylphenyl
A-68 2,6-di(trifluoromethoxy)phenyl A-102 3-chloro-4-methylphenyl
A-69 3,4-di(trifluoromethoxy)phenyl A-103 2-methyl-3-fluorophenyl
A-70 3,5-di(trifluoromethoxy)phenyl A-104 2-methyl-4-fluorophenyl
A-71 2,3-di(difluoromethoxy)phenyl A-105 2-methyl-5-fluorophenyl
A-72 2,4-di(difluoromethoxy)phenyl A-106 2-methyl-6-fluorophenyl
A-73 2,5-di(difluoromethoxy)phenyl A-107 3-methyl-4-fluorophenyl
A-74 2,6-di(difluoromethoxy)phenyl A-108 3-methyl-5-fluorophenyl
A-75 3,4-di(difluoromethoxy)phenyl A-109 2-fluoro-3-methylphenyl
A-76 3,5-di(difluoromethoxy)phenyl A-1 10 2-fluoro-4-methylphenyl
A-77 2,3- A-1 1 1 2-fluoro-5-methylphenyl di(trifluoromethylthio)phenyl A-1 12 3-fluoro-4-methylphenyl
A-78 2,4- A-1 13 2-chloro-3-ethylphenyl di(trifluoromethylthio)phenyl A-1 14 2-chloro-4-ethylphenyl
A-79 2,5- A-1 15 2-chloro-5-ethylphenyl di(trifluoromethylthio)phenyl A-1 16 3-chloro-4-ethylphenyl
A-80 2,6- A-1 17 2-ethyl-3-chlorophenyl di(trifluoromethylthio)phenyl A-1 18 2-ethyl-4-chlorophenyl
A-81 3,4- A-1 19 2-ethyl-5-chlorophenyl di(trifluoromethylthio)phenyl A-120 2-ethyl-6-chlorophenyl
A-82 3,5- A-121 3-ethyl-4-chlorophenyl di(trifluoromethylthio)phenyl A-122 3-ethyl-5-chlorophenyl
A-83 2-fluoro-3-chlorophenyl A-123 2-ethyl-3-fluorophenyl
A-84 2-fluoro-4-chlorophenyl A-124 2-ethyl-4-fluorophenyl
A-85 2-fluoro-5-chlorophenyl A-125 2-ethyl-5-fluorophenyl
A-86 2-fluoro-6-chlorophenyl A-126 2-ethyl-6-fluorophenyl
A-87 3-fluoro-4-chlorophenyl A-127 3-ethyl-4-fluorophenyl
A-88 3-fluoro-5-chlorophenyl A-128 3-ethyl-5-fluorophenyl row B row B
A-129 2-fluoro-3-ethylphenyl (trifluoromethyl)phenyl
A-130 2-fluoro-4-ethylphenyl A-162 2-chloro-5-
A-131 2-fluoro-5-ethylphenyl (trifluoromethyl)phenyl
A-132 3-fluoro-4-ethylphenyl A-163 3-chloro-4-
A-133 2-methoxy-3-chlorophenyl (trifluoromethyl)phenyl
A-134 2-methoxy-4-chlorophenyl A-164 2-(trifluoromethyl)-3-
A-135 2-methoxy-5-chlorophenyl fluorophenyl
A-136 2-methoxy-6-chlorophenyl A-165 2-(trifluoromethyl)-4-
A-137 3-methoxy-4-chlorophenyl fluorophenyl
A-138 3-methoxy-5-chlorophenyl A-166 2-(trifluoromethyl)-5-
A-139 2-chloro-3-methoxyphenyl fluorophenyl
A-140 2-chloro-4-methoxyphenyl A-167 2-(trifluoromethyl)-6-
A-141 2-chloro-5-methoxyphenyl fluorophenyl
A-142 3-chloro-4-methoxyphenyl A-168 3-(trifluoromethyl)-4-
A-143 2-methoxy-3-fluorophenyl fluorophenyl
A-144 2-methoxy-4-fluorophenyl A-169 3-(trifluoromethyl)-5-
A-145 2-methoxy-5-fluorophenyl fluorophenyl
A-146 2-methoxy-6-fluorophenyl A-170 2-fluoro-3-
A-147 3-methoxy-4-fluorophenyl (trifluoromethyl)phenyl
A-148 3-methoxy-5-fluorophenyl A-171 2-fluoro-4-
2-fluoro-3-methoxyphenyl (trifluoromethyl)phenyl
A-149
A-150 2-fluoro-4-methoxyphenyl A-172 2-fluoro-5-
(trifluoromethyl)phenyl
A-151 2-fluoro-5-methoxyphenyl
A-173 3-fluoro-4-
A-152 3-fluoro-4-methoxyphenyl
(trifluoromethyl)phenyl
A-153 3-fluoro-5-methoxyphenyl
A-174 2-(trifluoromethoxy)-3-
A-154 2-(trifluoromethyl)-3- chlorophenyl chlorophenyl
A-175 2-(trifluoromethoxy)-4-
A-155 2-(trifluoromethyl)-4- chlorophenyl chlorophenyl
A-176 2-(trifluoromethoxy)-5-
A-156 2-(trifluoromethyl)-5- chlorophenyl chlorophenyl
A-177 2-(trifluoromethoxy)-6-
A-157 2-(trifluoromethyl)-6- chlorophenyl chlorophenyl
A-178 3-(trifluoromethoxy)-4-
A-158 3-(trifluoromethyl)-4- chlorophenyl chlorophenyl
A-179 3-(trifluoromethoxy)-5-
A-159 3-(trifluoromethyl)-5- chlorophenyl chlorophenyl
A-180 2-chloro-3-
A-160 2-chloro-3-
(trifluoromethoxy)phenyl
(trifluoromethyl)phenyl
A-181 2-chloro-4-
A-161 2-chloro-4-
(trifluoromethoxy)phenyl row B row B
A-182 2-chloro-5- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-203 3-chloro-4-
A-183 3-chloro-4- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-204 2-(difluoromethoxy)-3-
A-184 2-(trifluoromethoxy)-3- fluorophenyl
fluorophenyl A-205 2-(difluoromethoxy)-4-
A-185 2-(trifluoromethoxy)-4- fluorophenyl
fluorophenyl A-206 2-(difluoromethoxy)-5-
A-186 2-(trifluoromethoxy)-5- fluorophenyl
fluorophenyl A-207 2-(difluoromethoxy)-6-
A-187 2-(trifluoromethoxy)-6- fluorophenyl
fluorophenyl A-208 3-(difluoromethoxy)-4-
A-188 3-(trifluoromethoxy)-4- fluorophenyl
fluorophenyl A-209 3-(difluoromethoxy)-5-
A-189 3-(trifluoromethoxy)-5- fluorophenyl
fluorophenyl A-210 2-fluoro-3-
A-190 2-fluoro-3- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-21 1 2-fluoro-4-
A-191 2-fluoro-4- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-212 2-fluoro-5-
A-192 2-fluoro-5- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-213 3-fluoro-4-
A-193 3-fluoro-4- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-214 2-(trifluoromethylthio)-3-
A-194 2-(difluoromethoxy)-3- chlorophenyl
chlorophenyl A-215 2-(trifluoromethylthio)-4-
A-195 2-(difluoromethoxy)-4- chlorophenyl
chlorophenyl A-216 2-(trifluoromethylthio)-5-
A-196 2-(difluoromethoxy)-5- chlorophenyl
chlorophenyl A-217 2-(trifluoromethylthio)-6-
A-197 2-(difluoromethoxy)-6- chlorophenyl
chlorophenyl A-218 3-(trifluoromethylthio)-4-
A-198 3-(difluoromethoxy)-4- chlorophenyl
chlorophenyl A-219 3-(trifluoromethylthio)-5-
A-199 3-(difluoromethoxy)-5- chlorophenyl
chlorophenyl A-220 2-chloro-3-
A-200 2-chloro-3- (trifluoromethylthio)phenyl
(difluoromethoxy)phenyl A-221 2-chloro-4-
A-201 2-chloro-4- (trifluoromethylthio)phenyl
(difluoromethoxy)phenyl A-222 2-chloro-5-
A-202 2-chloro-5- (trifluoromethylthio)phenyl row B row B
A-223 3-chloro-4- A-252 2,3,4-trimethoxyphenyl
(trifluoromethylthio)phenyl A-253 2,3,5-trimethoxyphenyl
A-224 2-(trifluoromethylthio)-3- A-254 2,3,6-trimethoxyphenyl fluorophenyl A-255 2,4,5-trimethoxyphenyl
A-225 2-(trifluoromethylthio)-4- A-256 2,4,6-trimethoxyphenyl fluorophenyl A-257 3,4,5-trimethoxyphenyl
A-226 2-(trifluoromethylthio)-5- A-258 phenyl
fluorophenyl A-259 2-chlorophenyl
A-227 2-(trifluoromethylthio)-6- A-260 3-chlorophenyl
fluorophenyl A-261 4-chlorophenyl
A-228 3-(trifluoromethylthio)-4- A-262 2-fluorophenyl
fluorophenyl A-263 3-fluorophenyl
A-229 3-(trifluoromethylthio)-5- A-264 4-fluorophenyl
fluorophenyl A-265 2-methylphenyl
A-230 2-fluoro-3- A-266 3-methylphenyl
(trifluoromethylthio)phenyl A-267 4-methylphenyl
A-231 2-fluoro-4- A-268 2-ethylphenyl
(trifluoromethylthio)phenyl A-269 3-ethylphenyl
A-232 2-fluoro-5- A-270 4-ethylphenyl
(trifluoromethylthio)phenyl
A-271 2-methoxyphenyl
A-233 3-fluoro-4- A-272 3-methoxyphenyl
(trifluoromethylthio)phenyl
A-273 4-methoxyphenyl
A-234 2,3,4-trichlorophenyl
A-274 2-trifluoromethylphenyl
A-235 2,3,5-trichlorophenyl
A-275 3-trifluoromethylphenyl
A-236 2,3,6-trichlorophenyl
A-276 4-trifluoromethylphenyl
A-237 2,4,5-trichlorophenyl
A-277 2-trifluoromethoxyphenyl
A-238 2,4,6-trichlorophenyl
A-278 3-trifluoromethoxyphenyl
A-239 3,4,5-trichlorophenyl
A-279 4-trifluoromethoxyphenyl
A-240 2,3,4-trifluorophenyl
A-280 2-difluoromethoxyphenyl
A-241 2,3,5-trifluorophenyl
A-281 3-difluoromethoxyphenyl
A-242 2,3,6-trifluorophenyl
A-282 4-difluoromethoxyphenyl
A-243 2,4,5-trifluorophenyl
A-283 2-trifluoromethylthiophenyl
A-244 2,4,6-trifluorophenyl
A-284 3-trifluoromethylthiophenyl
A-245 3,4,5-trifluorophenyl
A-285 4-trifluoromethylthiophenyl
A-246 2,3,4-trimethylphenyl
A-286 2,3-dichlorophenyl
A-247 2,3,5-trimethylphenyl
A-287 2,4-dichlorophenyl
A-248 2,3,6-trimethylphenyl
A-288 2,5-dichlorophenyl
A-249 2,4,5-trimethylphenyl
A-289 2,6-dichlorophenyl
A-250 2,4,6-trimethylphenyl
A-290 3,4-dichlorophenyl
A-251 3,4,5-trimethylphenyl
A-291 3,5-dichlorophenyl 1
row B row B
A-292 2,3-difluorophenyl A-332 3,4-di(difluoromethoxy)phenyl
A-293 2,4-difluorophenyl A-333 3,5-di(difluoromethoxy)phenyl
A-294 2,5-difluorophenyl A-334 2,3-
A-295 2,6-difluorophenyl di(trifluoromethylthio)phenyl
A-296 3,4-difluorophenyl A-335 2,4-
A-297 3,5-difluorophenyl di(trifluoromethylthio)phenyl
A-298 2,3-dimethylphenyl A-336 2,5-
A-299 2,4-dimethylphenyl di(trifluoromethylthio)phenyl
A-300 2,5-dimethylphenyl A-337 2,6-
A-301 2,6-dimethylphenyl di(trifluoromethylthio)phenyl
A-302 3,4-dimethylphenyl A-338 3,4-
A-303 3,5-dimethylphenyl di(trifluoromethylthio)phenyl
A-304 2,3-diethylphenyl A-339 3,5-
A-305 2,4-diethylphenyl di(trifluoromethylthio)phenyl
A-306 2,5-diethylphenyl A-340 2-fluoro-3-chlorophenyl
A-307 2,6-diethylphenyl A-341 2-fluoro-4-chlorophenyl
A-308 3,5-diethylphenyl A-342 2-fluoro-5-chlorophenyl
A-309 3,4-diethylphenyl A-343 2-fluoro-6-chlorophenyl
A-310 2,3-dimethoxyphenyl A-344 3-fluoro-4-chlorophenyl
A-31 1 2,4-dimethoxyphenyl A-345 3-fluoro-5-chlorophenyl
A-312 2,5-dimethoxyphenyl A-346 2-chloro-3-fluorophenyl
A-313 2,6-dimethoxyphenyl A-347 2-chloro-4-fluorophenyl
A-314 3,4-dimethoxyphenyl A-348 2-chloro-5-fluorophenyl
A-315 3,5-dimethoxyphenyl A-349 3-chloro-4-fluorophenyl
A-316 2,3-di(trifluoromethyl)phenyl A-350 2-methyl-3-chlorophenyl
A-317 2,4-di(trifluoromethyl)phenyl A-351 2-methyl-4-chlorophenyl
A-318 2,5-di(trifluoromethyl)phenyl A-352 2-methyl-5-chlorophenyl
A-319 2,6-di(trifluoromethyl)phenyl A-353 2-methyl-6-chlorophenyl
A-320 3,4-di(trifluoromethyl)phenyl A-354 3-methyl-4-chlorophenyl
A-321 3,5-di(trifluoromethyl)phenyl A-355 3-methyl-5-chlorophenyl
A-322 2,3-di(trifluoromethoxy)phenyl A-356 2-chloro-3-methylphenyl
A-323 2,4-di(trifluoromethoxy)phenyl A-357 2-chloro-4-methylphenyl
A-324 2,5-di(trifluoromethoxy)phenyl A-358 2-chloro-5-methylphenyl
A-325 2,6-di(trifluoromethoxy)phenyl A-359 3-chloro-4-methylphenyl
A-326 3,4-di(trifluoromethoxy)phenyl A-360 2-methyl-3-fluorophenyl
A-327 3,5-di(trifluoromethoxy)phenyl A-361 2-methyl-4-fluorophenyl
A-328 2,3-di(difluoromethoxy)phenyl A-362 2-methyl-5-fluorophenyl
A-329 2,4-di(difluoromethoxy)phenyl A-363 2-methyl-6-fluorophenyl
A-330 2,5-di(difluoromethoxy)phenyl A-364 3-methyl-4-fluorophenyl
A-331 2,6-di(difluoromethoxy)phenyl A-365 3-methyl-5-fluorophenyl row B row B
A-366 2-fluoro-3-methylphenyl A-406 2-fluoro-3-methoxyphenyl
A-367 2-fluoro-4-methylphenyl A-407 2-fluoro-4-methoxyphenyl
A-368 2-fluoro-5-methylphenyl A-408 2-fluoro-5-methoxyphenyl
A-369 3-fluoro-4-methylphenyl A-409 3-fluoro-4-methoxyphenyl
A-370 2-chloro-3-ethylphenyl A-410 3-fluoro-5-methoxyphenyl
A-371 2-chloro-4-ethylphenyl A-41 1 2-(trifluoromethyl)-3-
A-372 2-chloro-5-ethylphenyl chlorophenyl
A-373 3-chloro-4-ethylphenyl A-412 2-(trifluoromethyl)-4-
A-374 2-ethyl-3-chlorophenyl chlorophenyl
A-375 2-ethyl-4-chlorophenyl A-413 2-(trifluoromethyl)-5-
A-376 2-ethyl-5-chlorophenyl chlorophenyl
A-377 2-ethyl-6-chlorophenyl A-414 2-(trifluoromethyl)-6-
A-378 3-ethyl-4-chlorophenyl chlorophenyl
A-379 3-ethyl-5-chlorophenyl A-415 3-(trifluoromethyl)-4-
A-380 2-ethyl-3-fluorophenyl chlorophenyl
A-381 2-ethyl-4-fluorophenyl A-416 3-(trifluoromethyl)-5-
A-382 2-ethyl-5-fluorophenyl chlorophenyl
A-383 2-ethyl-6-fluorophenyl A-417 2-chloro-3-
A-384 3-ethyl-4-fluorophenyl (trifluoromethyl)phenyl
A-385 3-ethyl-5-fluorophenyl A-418 2-chloro-4-
A-386 2-fluoro-3-ethylphenyl (trifluoromethyl)phenyl
A-387 2-fluoro-4-ethylphenyl A-419 2-chloro-5-
A-388 2-fluoro-5-ethylphenyl (trifluoromethyl)phenyl
A-389 3-fluoro-4-ethylphenyl A-420 3-chloro-4-
2-methoxy-3-chlorophenyl (trifluoromethyl)phenyl
A-390
A-421
A-391 2-methoxy-4-chlorophenyl 2-(trifluoromethyl)-3- fluorophenyl
A-392 2-methoxy-5-chlorophenyl
A-422 2-(trifluoromethyl)-4-
A-393 2-methoxy-6-chlorophenyl
fluorophenyl
A-394 3-methoxy-4-chlorophenyl
A-423 2-(trifluoromethyl)-5-
A-395 3-methoxy-5-chlorophenyl
fluorophenyl
A-396 2-chloro-3-methoxyphenyl
A-424 2-(trifluoromethyl)-6-
A-397 2-chloro-4-methoxyphenyl
fluorophenyl
A-398 2-chloro-5-methoxyphenyl
A-425 3-(trifluoromethyl)-4-
A-399 3-chloro-4-methoxyphenyl
fluorophenyl
A-400 2-methoxy-3-fluorophenyl
A-426 3-(trifluoromethyl)-5-
A-401 2-methoxy-4-fluorophenyl
fluorophenyl
A-402 2-methoxy-5-fluorophenyl
A-427 2-fluoro-3-
A-403 2-methoxy-6-fluorophenyl
(trifluoromethyl)phenyl
A-404 3-methoxy-4-fluorophenyl
A-428 2-fluoro-4-
A-405 3-methoxy-5-fluorophenyl row B row B
(trifluoromethyl)phenyl A-449 2-fluoro-5-
A-429 2-fluoro-5- (trifluoromethoxy)phenyl
(trifluoromethyl)phenyl A-450 3-fluoro-4-
A-430 3-fluoro-4- (trifluoromethoxy)phenyl
(trifluoromethyl)phenyl A-451 2-(difluoromethoxy)-3-
A-431 2-(trifluoromethoxy)-3- chlorophenyl
chlorophenyl A-452 2-(difluoromethoxy)-4-
A-432 2-(trifluoromethoxy)-4- chlorophenyl
chlorophenyl A-453 2-(difluoromethoxy)-5-
A-433 2-(trifluoromethoxy)-5- chlorophenyl
chlorophenyl A-454 2-(difluoromethoxy)-6-
A-434 2-(trifluoromethoxy)-6- chlorophenyl
chlorophenyl A-455 3-(difluoromethoxy)-4-
A-435 3-(trifluoromethoxy)-4- chlorophenyl
chlorophenyl A-456 3-(difluoromethoxy)-5-
A-436 3-(trifluoromethoxy)-5- chlorophenyl
chlorophenyl A-457 2-chloro-3-
A-437 2-chloro-3- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-458 2-chloro-4-
A-438 2-chloro-4- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-459 2-chloro-5-
A-439 2-chloro-5- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-460 3-chloro-4-
A-440 3-chloro-4- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-461 2-(difluoromethoxy)-3-
A-441 2-(trifluoromethoxy)-3- fluorophenyl
fluorophenyl A-462 2-(difluoromethoxy)-4-
A-442 2-(trifluoromethoxy)-4- fluorophenyl
fluorophenyl A-463 2-(difluoromethoxy)-5-
A-443 2-(trifluoromethoxy)-5- fluorophenyl
fluorophenyl A-464 2-(difluoromethoxy)-6-
A-444 2-(trifluoromethoxy)-6- fluorophenyl
fluorophenyl A-465 3-(difluoromethoxy)-4-
A-445 3-(trifluoromethoxy)-4- fluorophenyl
fluorophenyl A-466 3-(difluoromethoxy)-5-
A-446 3-(trifluoromethoxy)-5- fluorophenyl
fluorophenyl A-467 2-fluoro-3-
A-447 2-fluoro-3- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-468 2-fluoro-4-
A-448 2-fluoro-4- (difluoromethoxy)phenyl
(trifluoromethoxy)phenyl A-469 2-fluoro-5- row B row B
(difluoromethoxy)phenyl fluorophenyl
A-470 3-fluoro-4- A-487 2-fluoro-3-
(difluoromethoxy)phenyl (trifluoromethylthio)phenyl
A-471 2-(trifluoromethylthio)-3- A-488 2-fluoro-4- chlorophenyl (trifluoromethylthio)phenyl
A-472 2-(trifluoromethylthio)-4- A-489 2-fluoro-5- chlorophenyl (trifluoromethylthio)phenyl
A-473 2-(trifluoromethylthio)-5- A-490 3-fluoro-4- chlorophenyl (trifluoromethylthio)phenyl
A-474 2-(trifluoromethylthio)-6- A-491 2,3,4-trichlorophenyl
chlorophenyl A-492 2,3,5-trichlorophenyl
A-475 3-(trifluoromethylthio)-4- A-493 2,3,6-trichlorophenyl
chlorophenyl A-494 2,4,5-trichlorophenyl
A-476 3-(trifluoromethylthio)-5- A-495 2,4,6-trichlorophenyl
chlorophenyl A-496 3,4,5-trichlorophenyl
A-477 2-chloro-3- A-497 2,3,4-trifluorophenyl
(trifluoromethylthio)phenyl A-498 2,3,5-trifluorophenyl
A-478 2-chloro-4- A-499 2,3,6-trifluorophenyl
(trifluoromethylthio)phenyl A-500 2,4,5-trifluorophenyl
A-479 2-chloro-5- A-501 2,4,6-trifluorophenyl
(trifluoromethylthio)phenyl A-502 3,4,5-trifluorophenyl
A-480 3-chloro-4- A-503 2,3,4-trimethylphenyl
(trifluoromethylthio)phenyl A-504 2,3,5-trimethylphenyl
A-481 2-(trifluoromethylthio)-3- A-505 2,3,6-trimethylphenyl fluorophenyl A-506 2,4,5-trimethylphenyl
A-482 2-(trifluoromethylthio)-4- A-507 2,4,6-trimethylphenyl fluorophenyl A-508 3,4,5-trimethylphenyl
A-483 2-(trifluoromethylthio)-5- A-509 2,3,4-trimethoxyphenyl fluorophenyl
A-510 2,3,5-trimethoxyphenyl
A-484 2-(trifluoromethylthio)-6- A-51 1 2,3,6-trimethoxyphenyl fluorophenyl
A-512 2,4,5-trimethoxyphenyl
A-485 3-(trifluoromethylthio)-4-
A-513 2,4,6-trimethoxyphenyl fluorophenyl
A-514 3,4,5-trimethoxyphenyl
A-486 3-(trifluoromethylthio)-5-
Experimental Procedures
The following examples further illustrate the present invention and do not restrict the invention in any manner. Synthesis of bis-{1-[3-(2-chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]-1 H- [1,2,4]triazole-5-yl}-disulfide
To a suspension of (2RS, 3SR)-4-amino-2-[3-(2-chloro-phenyl)-2-(2,4-difluoro-phenyl)- oxiranylmethyl]-2,4-dihydro-[1 ,2,4]triazole-3-thione (10.0 g, 25.3 mmol) in a mixture of 40 ml. n-butanol and 40 ml. of n-butyl acetate was added n-butylnitrite (5.0 g, 48.5 mmol). The mixture was stirred overnight (16 h) at room temperature. Then, the formed precipitate was filtered off and then washed with cold n-butanol and dried under reduced pressure (p<20 mbar) at 50 °C overnight. The product was obtained as a 1 : 1 mixture of diastereomers in the form of a colorless solid (9.0 g, 1 1 .9 mmol, 94% yield) 1 H NMR (CDCI3, 500 MHz): δ (ppm) = 7.67 (s, 2 H); 7.56-7.60 (m, 2 H); 7.42-7.48 (m, 2 H); 7.31 -7.38 (m, 4 H); 7.18 (t, J = 10.5 Hz, 1 H); 7.16 (t, J = 10.5 Hz, 1 H); 6.75-6.86 (m, 4 H); 4.79 (d, J = 18.5 Hz, 2 H); 4.25 (s, 2 H); 4.04-4.14 (m, 2 H).
Melting point: 140 °C
Synthesis of (2RS, 3SR)-2-[3-(2-chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]- 2,4-dihydro-[1,2,4]triazole-3-thione from the disulfide with sodium dithionite in ethyl acetate/water
A s o l ut i o n of b i s-{1 -[3-(2-chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]-1 H- [1 ,2,4]triazole-5-yl}-disulfide (5.0 g, 6.6 mmol) in 50 ml. of ethyl acetate was treated with a solution of sodium dithionite (10% solution in water, 20 ml.) at room temperature. Stirring was continued for 60 min, then the phases were separated and the organic phase dried with sodium sulfate. Evaporation of all volatiles under reduced pressure gave the desired compound as a colorless solid (4.8 g, 12.6 mmol, 95% yield).
1 H NMR (DMSO-d6, 500 MHz): δ (ppm) = 13.31 (bs, 1 H); 8.23 (s, 1 H); 7.56-7.60 (m, 2 H); 7.44-7.49 (m, 2 H); 7.35 (q, J = 8.0 Hz, 1 H); 7.26 (dt, J = 2.5 Hz, J = 9.5 Hz, 1 H); 7.01 -7.06 (m, 1 H); 4.47 (d, J = 14.5 Hz, 1 H); 4.39 (s, 1 H); 4.13 (d, J = 14.5 Hz, 1 H). 13C NMR (DMSO-d6, 125 MHz): δ (ppm) = 166.0; 162.4 (dd, J = 12.1 Hz, J = 246 Hz); 160.6 (dd, J = 13.0 Hz, J = 249 Hz); 139.2; 132.7; 131 .5; 130.1 (dd, J = 7.8 Hz, J = 15.8 Hz); 130.0; 129.3; 128.0; 127.1 ; 120.9 (dd, J = 5.4 Hz, J = 13.3 Hz); 1 1 1.1 (dd, J = 6.0 Hz, J = 19.1 Hz); 103.9 (t, J = 25.4 Hz); 62.1 ; 61 .2; 47.5.
Melting point: 180 °C
Synthesis of (2RS, 3SR)-2-[3-(2-chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]- 2,4-dihydro-[1,2,4]triazole-3-thione from the disulfide with sodium borohydride and acetic acid in iso-butanol/tetrahydrofuran
A s l u r r y o f b i s-{1 -[3-(2-chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]-1 H- [1 ,2,4]triazole-5-yl}-disulfide (7.6 g, 10.0 mmol) and acetic acid (2.4 g, 40.0 mmol) in 50 ml. of ethanol was treated portionwise with sodium borohydride (0.4 g, 10.6 mmol). Upon complete addition the mixture was stirred for another 2 h at room temperature. Then, 50 ml. of a saturated sodium bicarbonate solution in water were added, followed by 50 ml. of ethyl acetate. The phases were separated and the aqueous phase was extracted with 50 ml. of ethyl acetate. The combined organic phases were successively washed with water and saturated aqueous sodium chloride solution. The crude material was obtained after evaporation of all volatiles. The residue was recrystallized from o- xylene (20 ml.) to give the product as a colorless solid (3.1 g, 8.2 mmol, 41 % yield). One-pot synthesis of bis-{ 1 -[3-(2-chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]- 1 H-[1 ,2,4]triazole-5-yl}-disulfide from the aminotriazolethione
(2RS, 3SR)-4-amino-2-[3-(2-chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl]-2,4- dihydro-[1 ,2,4]triazole-3-thione (25.0 g, 63.3 mmol) was dissolved in 75 g of tetrahydro- furan at 30 °C. To the clear solution was added 75 g of iso-butanol, followed by the dropwise addition of iso-butylnitrite (7.2 g, 66.5 mmol). Upon complete addition, the solution was kept at 30 °C for 3 h. Then sodium dithionite (10% solution in water, 1 10 g) was added and the biphasic mixture was stirred for 10 min. The phases were separated and the organic phase was successively washed with water and saturated aqueous sodium chloride solution (both 50 g). Then, 75 g of iso-butanol were added and the solution was stepwise warmed to 80 °C with concomitant lowering of the pressure to 300 mbar. The solution was concentrated to an end volume of 120 ml. and then cooled to 0 °C. The precipitated solid was filtered off, washed with cold iso-butanol and dried at 60 °C and p<20 mbar overnight. The product was obtained as a colorless solid (19.7 g, 92% wt.-% by HPLC, 76% yield).
One-pot synthesis of (2RS, 3SR)-2-[3-(2-chloro-phenyl)-2-(2,4-difluoro-phenyl)- oxiranylmethyl]-2,4-dihydro-[1,2,4]triazole-3-thione from methanesulfonic acid
(2RS, 3SR)-3-(2-chloro-phenyl)-2-(2,4-difluoro-phenyl)-oxiranylmethyl ester without isolation of any intermediates
A mixture of methanesulfonic acid (2RS, 3SR)-3-(2-chloro-phenyl)-2-(2,4-difluoro- phenyl)-oxiranylmethyl ester (24.3 g, 64.8 mol) and 4-amino-1 ,2,4-triazole (6.0 g, 71.4 mmol) in 10.7 g of n-butanol was heated to reflux for 5.5 h. Then, additional n- butanol (39 g) was added and the solution was cooled to 60 °C. Tetrahydrofuran (70 g) and powdered sulfur (2.1 g, 65.5 mmol) were added, followed by the slow addition of an aqueous solution of potassium carbonate (25% in water, 39.4 g, 71.3 mmol). The biphasic mixture was stirred at 60 °C for 1 h and then cooled to room temperature. The phases were separated and the organic layer washed with saturated sodium chloride solution (40 g). The mixture was then warmed to 30 °C and n-butyl nitrite (8.5 g, 74.4 mmol) was added over 10 min and stirring at 30 °C was continued for 3 h and then cooled to room temperature. An aqueous solution of sodium dithionite (4% in water, 35.2 g, 8.1 mmol) was added and stirring continued for 15 min. The organic phase was then washed with water twice (both 50 g). Then, 50 g of o-xylene were added and the solution warmed to 60 °C. The pressure was stepwise reduced to 200 mbar. Then, another 100 g of o-xylene were added and distillation continued to a pressure of 40 mbar. The suspension was then cooled to 0 °C, filtered and washed with o-xylene (50 g). The solid was dried overnight at 60 °C under reduced pressure to give the product as a colorless solid (19.2 g, 96% purity by HPLC, 48.3 mmol, 75% yield).

Claims

Claims:
A process for the preparation of 2-substituted 2,4-dihydro-[1 ,2,4]triazole- 3-thiones of the formula (III)
Figure imgf000128_0001
wherein
R is a group (1 )
Figure imgf000128_0002
wherein # shall mean the point of attachment to the triazolo group, and A and B are defined as follows:
A or B is a three-, four-, five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated heterocycle or five-, six-, seven-, eight-, nine- or ten-membered aromatic heterocycle, where the heterocycle contains in each case one, two, three or four heteroatoms from the group consisting of O, N and S; is naphthyl or phenyl; and the respective other variable B or A has one of the meanings mentioned above for A or B or is Ci-Cs-alkyl, C-i-Cs-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, or benzodioxolyl; where A and/or B independently of one another are unsubstituted or substituted by one, two, three or four independently selected substitu- ents L; wherein is halogen, cyano, nitro, cyanato (OCN), C-i-Cs-alkyl, Ci-Cs- haloalkyl, phenyl-Ci-C6-alkyloxy, C2-Cs-alkenyl, C2-Cs-halo- alkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, C4-Cio-alkadienyl, C4- Cio-haloalkadienyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs- alkylcarbonyloxy, d-Cs-alkylsulfonyloxy, C2-C8-alkenyloxy, C2- Cs-haloalkenyloxy, C2-C8-alkynyloxy, C2-C8-haloalkynyloxy, Cs- Cs-cycloalkyl, C3-Cs-halocycloalkyl, Cs-Cs-cycloalkenyl, C3-C8- halocycloalkenyl, Cs-Cs-cycloalkoxy, C3-C6-cycloalkenyloxy, hydroxyimino-Ci-Cs-alkyl, Ci-C6-alkylene, oxy-C2-C4-alkylene, oxy-Ci-C3-alkyleneoxy, Ci-Cs-alkoximino-Ci-Cs-alkyl, C2-C8- alkenyloximino-Ci-Ce-a I k y I , C2-C8-alkynyloximino-Ci-C8-alkyl, S(=0)nA1 , C(=0)A2, C(=S)A2, NAW, phenyl-Ci-Ce-alkyl, phenyl, phenyloxy o r a f i v e- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S; where n, A1 , A2, A5, A6 are: n is 0, 1 or 2;
A1 is hydrogen, hydroxyl, Ci-Cs-alkyl, Ci-Cs-haloalkyl, amino, Ci-C8-alkylamino or di-d-Cs-alkylamino,
A2 is one of the groups mentioned for A1 or C2-Cs-alkenyl, C2- Cs-haloalkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, Ci-Cs-alk- oxy, Ci-Cs-haloalkoxy, C2-C8-alkenyloxy, C2-Cs-halo- alkenyloxy, C2-C8-alkynyloxy, C2-C8-haloalkynyloxy, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkoxy or C3- Cs-halocycloalkoxy;
A5, A6 independently of one another are hydrogen, Ci-Cs- alkyl, Ci-Cs-haloalkyl, C2-Cs-alkenyl, C2-C8-haloalkenyl, C2- Cs-alkynyl, C2-C8-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, C3-Cs-cycloalkenyl or Cs-Cs-halocyclo- alkenyl; where the aliphatic and/or alicyclic and/or aromatic groups of the radical definitions of L for their part may carry one, two, three or four identical or different groups RL:
RL is halogen, cyano, nitro, d-Cs-alkyl, Ci-Cs-haloalkyl, Ci-Cs- alkoxy, Ci-Cs-haloalkoxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cycloalkenyl, Cs-Cs-cycloalkoxy, C3-C8- halocycloalkoxy, Ci-Cs-alkylcarbonyl, Ci-Cs- alkylcarbonyloxy, Ci-Cs-alkoxycarbonyl, amino, Ci-Cs- alkylamino, di-Ci-Cs-alkylamino; or group (2)
Figure imgf000129_0001
# shall mean the point of attachment to the triazolo group and R11 and R22 have the following meanings:
R11, R22 independently of one another Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl or phenyl, wherein the alkyl, cy- cloalkyl and phenyl moieties may be unsubstituted or substituted by one, two, three or four substituents L; or
R11 and R22, together with the carbon atom to which they are attached, form a five- or six-membered saturated or partially unsaturated ring, that can be unsubstituted or substituted by one, two, three, four or five substituents L', wherein L' stands for L as defined above or stands for a group
R33
F
-.44
wherein R33 and R44 independently are selected from the group of hydrogen and the meaning for L as defined above;
Figure imgf000130_0001
wherein
# shall mean the point of attachment to the triazolo group and R55, R66 and R77 have the following meanings:
R55 phenyl-Ci-Ce-alkyl, phenyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S; where the aliphatic and/or aromatic and/or heterocyclic groups for their part may carry one, two, three or four identical or different groups selected from halogen, cyano, nitro, Ci-Cs-alkyl, Ci-Cs-haloalkyl, d-Cs-alkoxy, d-Cs-haloalkoxy, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, Cs-Cs-cycloalkenyl, Cs-Cs-cycloalkoxy, C3-C8- halocycloalkoxy, d-Cs-alkylcarbonyl, d-Cs-alkylcarbonyloxy, d- Cs-alkoxycarbonyl, amino, d-Cs-alkylamino, di-d-Cs-alkylamino, phenyl, halophenyl, phenyloxy, halophenyloxy; R66, R77 independently of one another are hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl or phenyl, wherein the alkyl, cycloalkyl or phenyl moieties may be unsubstituted or substituted by one, two or three substituents selected from halogen, cyano, nitro, Ci-Cs-alkyl, Ci-Cs-haloalkyl, d-Cs-alkoxy,
Ci-Cs-haloalkoxy; comprising the steps i) diazotation of 2-substituted 4-amino-2,4-dihydro-[1 ,2,4]triazole-3-thiones of formula of the formula (I)
Figure imgf000131_0001
wherein
R is defined as above by treatment with inorganic nitrites and an acid or in the presence of organic nitrites in an organic solvent or water or mixtures thereof giving the corresponding compound of the formula (VIII),
Figure imgf000131_0002
wherein
R is defined as above,
Y- is an anion selected from fluoride, chloride, bromide, iodide, arylsul- fonate, alkylsulfonate, haloalkylsulfonate or X01OSO3, in which X01 is
Ci-Cs-alkyl, Ci-Cs-haloalkyl or Cs-Cs-cycloalkyl where above mentioned alkyl, haloalkyl or aryl groups are unsubstituted or substituted by one, two, three or four independently selected inert substituents- sulfate, sulfonate, phosphate, phosponate, tetrafluoroborate, tetra- phenylborate, hexafluorophosphate, hexafluoroarsenate, hex- afluoroantimonate, trifluoroacetate, trichloroacetate, perchlorate, Ci-Cio-alkoxide or hydroxide; reduction of a compound of the formula (VIII) to provide mixtures of compounds of the formula (III) and compounds of the formula (VII),
Figure imgf000132_0001
wherein
R is defined as above, by means of a reducing agent; iii) treating the reaction mixture with a reducing reagent suitable to cleave disulfide groups.
The process according to claim 1 , wherein step (i), step (ii) and step (iii) are conducted in one vessel.
The process according to claim 1 or 2, wherein the solvent is water, Ci-Cs- alkanols, branched or unbranched Ci-Cio-alkanes, alicyclic hydrocarbons, aromatic hydrocarbons, branched or unbranched Ci-Cio-alkanes substituted by halogen, di-Ci-C6-alkyl ethers, Ci-C6-alkyl Cs-Cs-cycloalkyl ethers, substituted phenyl alkyl ethers, cyclic ethers, nitriles, di-Ci-C6-alkyl ketones, cyclic ketones, carbonic esters of d-Cs-alkanols, Ν,Ν-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, tetramethylurea or mixtures thereof.
4. The process according to claim 1 or 2, wherein the solvent is water or protic solvents or mixtures of water and protic solvents.
The process according to any one of claim 1 to 4, wherein the diazotation step i) involves the use of an alkaline metal nitrite and an acid.
The process according to claim 1 or 2, wherein the diazotation step i) involves the use of Ci-Cio-alkylnitrites.
The process according to claim 1 or 2, wherein the reducing agent of step (ii) is selected from the group consisting of Ci-Cio-alkanols or formic acid and its salts, formic esters, formic amides or mercaptanes or alkaline metal borohydrides or tin(ll) salts. 8. The process according to claim 1 or 2, wherein the reducing agent of step (iii) is alkali metal or alkaline earth metal dithionite, alkali metal formate, sulfur dioxide, hydrazine, zinc/ammonium chloride, alkali metal alanate or mixtures thereof.
9. The process according to any one of claims 1 to 8, wherein R is a group (1 ) as defined in claim 1 .
10. The process according to any one of claims 1 to 8, wherein R is a group (2) as defined in claim 1 . 1 1 . The process according to any one of claims 1 to 8, wherein R is a group (3) as defined in claim 1 .
12. Compounds of the formula (VIII), in which R is a group (1 ) as defined in claim 1 . 13. Compounds of the formula (VIII), in which R is a group (2) as defined in claim 1 .
14. Compounds of the formula (VIII), in which R is a group (3) as defined in claim 1 .
PCT/EP2012/057230 2011-04-28 2012-04-20 Process for the preparation of 2-substituted 2,4-dihydro-[1,2,4]triazole-3-thiones WO2012146535A1 (en)

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CN111269190A (en) * 2018-12-04 2020-06-12 北京颖泰嘉和生物科技股份有限公司 Method for synthesizing triazoline thioketone compound by one-pot method

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CN111269190A (en) * 2018-12-04 2020-06-12 北京颖泰嘉和生物科技股份有限公司 Method for synthesizing triazoline thioketone compound by one-pot method

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